EP3325467A1 - Substituted heteroaryl carboxylic acid hydrazides or salts thereof and use thereof to increase stress tolerance in plants - Google Patents

Substituted heteroaryl carboxylic acid hydrazides or salts thereof and use thereof to increase stress tolerance in plants

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Publication number
EP3325467A1
EP3325467A1 EP16741278.2A EP16741278A EP3325467A1 EP 3325467 A1 EP3325467 A1 EP 3325467A1 EP 16741278 A EP16741278 A EP 16741278A EP 3325467 A1 EP3325467 A1 EP 3325467A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
aryl
heteroaryl
methyl
alkoxycarbonyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP16741278.2A
Other languages
German (de)
French (fr)
Inventor
Jens Frackenpohl
Guido Bojack
Marco BRÜNJES
Hendrik Helmke
Stefan Lehr
Peter BRÜCHNER
Jörg Tiebes
Marc Mosrin
Jan Dittgen
Dirk Schmutzler
Philippe Desbordes
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
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Bayer CropScience AG
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Filing date
Publication date
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Publication of EP3325467A1 publication Critical patent/EP3325467A1/en
Withdrawn legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/16—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/06—1,2,3-Thiadiazoles; Hydrogenated 1,2,3-thiadiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

Definitions

  • the invention relates to substituted Heteroarylcarbonsaurehydrazide or their salts and their use for increasing the stress tolerance in plants to abiotic stress, and to increase plant growth and / or to increase the plant yield.
  • substituted azinylcarboxamides such as, for example, substituted 4- (trifluoromethyl) nicotinamides, possess insecticidal properties (cf., for example, EP185256, WO2001 / 014373, WO2002 / 022583, JP07010841, JP07025853, WO2005 / 1 13553).
  • N-substituted Azinylalkylazincarboxamide and their insecticidal activity are described in DE102008041214, wherein as N-substituents of the amides in question, for example, alkyl, arylcarbonyl, alkylcarbonyl,
  • abiotic stress defense reactions e.g., cold, heat, drought, salt, flooding
  • signal transduction chains e.g., transcription factors, kinases, phosphatases
  • the signal chain genes of the abiotic stress reaction include, among others.
  • Late Embryogenesis Abundant Proteins which include dehydrins as an important class, is known (Ingram and Bartels, 1996, Annu Rev Plant Physiol Plant Mol Biol 47: 277-403, Close, 1997, Physiol Plant 700: 291-296). These are chaperones, the vesicles, proteins and
  • HSF Heat Shock Factors
  • HSP Heat Shock Proteins
  • Substances or their stable synthetic derivatives and derived structures are also effective in external application to plants or seed dressing and activate defense reactions that result in an increased stress or pathogen tolerance of the plant [Sembdner, and Parthier, 1993, Ann. Rev. Plant Physiol. Plant Mol. Biol. 44: 569-589].
  • naphthylsulfonamide (4-bromo-N- (pyridin-2-ylmethyl) naphthalene-1-sulfonamide) influences the germination of plant seeds in the same manner as abscisic acid (Park et al., Science 2009, 324, 1068-1071).
  • a naphthylsulfamidocarboxylic acid (N - [(4-bromo-1-naphthyl) sulfonyl] -5-methoxynorvaline) exhibits a mode of action in biochemical receptor assays that react with 4-bromo-N- (pyridin-2-ylmethyl) naphthalene-1-sulfonamide is comparable (Melcher et al., Nature Structural & Molecular Biology 2010, 17, 1, 102-1 108).
  • N- (6-aminohexyl) -5-chloronaphthalene-1-sulfonamide affects calcium levels in plants that have been cold shocked (Cholewa et al., Can. J. Botany 1997, 75, 375- 382). Similar effects are observed even when using fungicides, in particular from the group of strobilurins or succinate dehydrogenase inhibitors, which are often accompanied by an increase in yield (Draber et al., DE3534948, Bartlett et al., 2002, Pest Management, 60: 309 ). It is also known that the low dose herbicide glyphosate stimulates the growth of some plant species (Cedergreen, Env. Pollution 2008, 156, 1099).
  • osmolytes e.g. Glycine betaine or its biochemical precursors, e.g. Choline derivatives
  • Xanthines for increasing the abiotic stress tolerance in plants has already been described (Bergmann et al., DD277832, Bergmann et al., DD277835).
  • the molecular causes of the anti-stress effects of these substances are largely unknown.
  • PARP poly-ADP-ribose polymerases
  • PARG poly (ADP-ribose) glycohydrolases
  • the object of the present invention was to provide compounds which further increase the tolerance to abiotic stress in plants, cause a strengthening of plant growth and / or contribute to the increase of the plant yield.
  • tolerance to abiotic stress for example, tolerance to cold, heat,
  • Heteroarylcarbonklahydrazide can be used to increase the stress tolerance in plants to abiotic stress, as well as to increase plant growth and / or increase the plant yield.
  • the subject of the present invention are therefore substituted
  • R 1 , R 2 and R 7 independently of one another represent hydrogen, halogen, cyano, nitro,
  • X 1 , X 2 and X 3 are the same or different and are each independently O.
  • Grouping NR 20 are, but in no case adjacent to an O and S atom and in each case in each case more than one O or S atom in the formed 5-membered ring is contained, and wherein R 2 in the grouping CR 2 and R 20 in the moiety NR 20 each have the same or different meanings according to the above or below definitions, W is O (oxygen) or S (sulfur),
  • a 1 , A 2 , A 3 , A 4 and A 5 are the same or different and are independently N (nitrogen) or the group CR 7 , but in no case more than two N atoms are adjacent, and wherein R 7 in the group CR 7 each have the same or different meanings according to the above
  • R 3 is (Ci-Cs) alkyl, cyano (Ci-C 8) -alkyl, (C 2 -C 8) -alkenyl, (C 2 -C 8) -alkynyl, (C1-C10) - haloalkyl , (C 2 -C 8 ) -haloalkenyl, (C 2 -C 8 ) -haloalkynyl, (C 3 -C 10) -cycloalkyl,
  • R 4 is hydrogen, (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, (C 1 -C 10) -haloalkyl, (C 2 -C 8 ) -haloalkenyl , (C 2 -C 8 ) -haloalkynyl, (C 3 -Cio) -cycloalkyl,
  • R 5 and R 6 independently of one another represent hydrogen, (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, (C 1 -C 10) -haloalkyl, (C 2 -) C 8 ) -haloalkenyl, (C 2 -C 8 ) -haloalkynyl, (C 3 -C 10) -cycloalkyl, (C 3 -C 10) -halocycloalkyl, (C 1 -C 10) -cycloalkenyl, (C 1 -C 8 ) -halocycloalkenyl, aryl, aryl (Ci-C 8) alkyl, heteroaryl, heteroaryl (Ci-C 8) alkyl, (C3-C8) -Cycloal alkyl- (Ci-C8) -alkyl, heterocyclyl,
  • R 1 and X 1 when X 1 is a group CR 2 , with the atoms to which they are attached, a fully saturated, partially saturated or completely
  • X 1 and X 2 when both represent a group CR 2 , with the atoms to which they belong
  • a 1 and A 2 when both represent a group CR 7 , with the atoms to which they belong
  • a 2 and A 3 when both represent a group CR 7 , with the atoms to which they belong
  • a 3 and A 4 when both represent a group CR 7 , with the atoms to which they belong
  • R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 independently of one another represent hydrogen, halogen, (C 1 -C 8 ) alkyl, (C 2 -C 8) alkenyl, (C 2 -C 8) -alkynyl, (C1-C10) - haloalkyl, (C 2 -C 8) -haloalkenyl, (C 2 -C 8) haloalkynyl, (C 3 -Cio) cycloalkyl, aryl, aryl (Ci-C 8) alkyl, heteroaryl, heteroaryl (Ci-C 8) alkyl, (C 3 -C 8) -cycloalkyl- (Ci-Cs) alkyl, heterocyclyl, heterocyclyl (Ci-C8) alkyl, (Ci-C 8) alk
  • R 5 and R 6 with the atom to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring,
  • R 20 is hydrogen, (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, (C 1 -C 10) -haloalkyl, (C 2 -C 8 ) -haloalkenyl , (C 2 -C 8 ) -haloalkynyl, (C 3 -Cio) -cycloalkyl,
  • R 21 and R 22 are the same or different and independently of each other
  • Hydrogen (Ci-C 8) alkyl, (C 2 -C 8) alkenyl, (C 2 -C 8) -alkynyl, (Ci-C 8) cyanoalkyl, (Ci-Cio) -haloalkyl, (C 2 -C 8 ) -haloalkenyl, (C 2 -C 8 ) -haloalkynyl, (C 3 -C 10) -cycloalkyl (C 3 -C 10) -halocycloalkyl, (C 4 -C 10) -cycloalkenyl, (C 4 -C 10) - Halocycloalkenyl,
  • R 24 is hydrogen, (Ci-C 8) alkyl, (C 2 -C 8) alkenyl, (C 2 -C 8) -alkynyl, (Ci-C 8) - cyanoalkyl, (Ci-Cio) -haloalkyl , (C 2 -C 8 ) -haloalkenyl, (C 2 -C 8 ) -haloalkynyl, (C 3 -C 10) -cycloalkyl, (C 3 -C 10) -halocycloalkyl, (C 1 -C 8 ) -cycloalkenyl, Cio) - halocycloalkenyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -haloalkyl aryl, aryl- (C 1
  • the compounds of general formula (I) may be prepared by addition of a suitable inorganic or organic acid such as, for example, mineral acids such as HCl, HBr, H 2 SO 4 , H 8 PO 4 or HNO 3 , or organic acids, e.g.
  • a suitable inorganic or organic acid such as, for example, mineral acids such as HCl, HBr, H 2 SO 4 , H 8 PO 4 or HNO 3 , or organic acids, e.g.
  • carboxylic acids such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or sulfonic acids such as p-toluenesulfonic acid to form a basic group such as amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino, salts.
  • These salts then contain the conjugate base of the acid as an anion.
  • Sulfonic acids certain sulfonic acid amides or carboxylic acids are present, internal salts can in turn form protonatable groups, such as amino groups.
  • Suitable bases are, for example, organic amines, such as trialkylamines, morpholine, piperidine and pyridine, and ammonium, alkali or alkaline earth metal hydroxides, carbonates and bicarbonates, in particular sodium and potassium hydroxide, sodium and potassium carbonate and sodium and
  • Hydrogen is replaced by a cation suitable for agriculture
  • metal salts in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or ammonium salts, salts with organic amines or quaternary ammonium salts, for example with cations of the formula [NR a R b R c R d ] + , wherein R a to Each R d is independently one
  • alkylsulfonium and Alkylsulfoxoniumsalze such as (Ci-C4) - trialkylsulfonium and (Ci-C 4) -Trialkylsulfoxoniumsalze.
  • the Heteroarylcarbonklarehydrazide of the formula (I) may, depending on external conditions such as pH, solvent, and temperature, as well as X 1, X 2 are present, and X 3 in different tautomeric structures, all of which are intended to be embraced by the general formula (I) ,
  • the compounds of the formula (I) used according to the invention and their salts are referred to below as "compounds of the general formula (I)".
  • Preferred subject of the invention are compounds of the general formula (I) wherein
  • R 1 , R 2 and R 7 independently of one another represent hydrogen, halogen, cyano, nitro,
  • C -C7 Halocycloalkenyl, pentafluorosulfanyl, (Ci-C7) alkoxy (Ci-C7) haloalkyl,
  • (C 1 -C 7 ) -haloalkylthio (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkylcarbonyl- (C 1 -C 7 ) -alkyl, COOR 23 , CONR 21 R 22 , COR 23 , -C NOR 23, R 21 R 22 N- (C 7) alkyl, R 23 OOC- (C 7) alkyl, aryl (Ci-C7) alkynyl, heteroaryl (Ci-C 7) alkynyl, heterocyclyl (Ci-C7) alkynyl, tris [(Ci-C 7) alkyl] silyl (C 2 -C 7) alkynyl, - bis [(Ci-C 7) alkyl] (aryl) silyl (C 2 -C 7) alkynyl, bis-aryl [(Ci-C 7) alkyl] (aryl) silyl (
  • X 1 , X 2 and X 3 are the same or different and are each independently O.
  • Grouping NR 20 are, but in no case adjacent to an O and S atom and in each case in each case more than one O or S atom in the formed 5-membered ring is contained, and wherein R 2 in the grouping CR 2 and R 20 in moiety NR 20 each have the same or different meanings according to the above or below definitions, W is O (oxygen) or S (sulfur),
  • a 1 , A 2 , A 3 , A 4 and A 5 are the same or different and are independently N (nitrogen) or the group CR 7 , but in no case more than two N atoms are adjacent, and wherein R 7 in the group CR 7 has the same or different meanings as defined above,
  • R 3 is (C 7) alkyl, cyano (Ci-C7) alkyl, (C 2 -C 7) alkenyl, (C 2 -C 7) alkynyl, (Ci-C7) - Haloalkyl, (C 2 -C 7 ) -haloalkenyl, (C 2 -C 7 ) -haloalkynyl, (C 3 -C 7 ) -cycloalkyl, (C 3 -C 7 ) -halocycloalkyl, (C 4 -C 7 ) - cycloalkenyl, (C 4 -C 7) -Halocycloalkenyl, aryl, aryl (Ci-C7) alkyl, heteroaryl, heteroaryl (Ci-C7) alkyl, (C 3 -C 7) -cycloalkyl- ( Ci-C7) - alkyl, heterocyclyl, heterocyclyl (Ci-C7) al
  • R 4 represents hydrogen, (Ci-C7) alkyl, (C 2 -C 7) alkenyl, (C 2 -C 7) alkynyl, (Ci-C7) -
  • R 1 and X 1 when X 1 is a group CR 2 , with the atoms to which they are attached, a fully saturated, partially saturated or completely
  • X 1 and X 2 when both represent a group CR 2 , with the atoms to which they belong
  • a 1 and A 2 when both represent a group CR 7 , with the atoms to which they belong
  • a 2 and A 3 when both represent a group CR 7 , with the atoms to which they are attached form a fully saturated, partially saturated or fully unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring, and
  • a 3 and A 4 when both represent a group CR 7 , with the atoms to which they belong
  • R 20 is hydrogen, (Ci-C7) alkyl, (C 2 -C 7) alkenyl, (C 2 -C 7) alkynyl, (Ci-C7) -
  • Haloalkyl (C 2 -C 7 ) -haloalkenyl, (C 2 -C 7 ) -haloalkynyl, (C 3 -C 7 ) -cycloalkyl, (C 7 -C 7 ) -cycloalkenyl, (C 1 -C 7 ) -alkoxy, aryl, heteroaryl, heterocyclyl, (Ci-C7) - Al kylcarbonyl, aryl (Ci-C7) Al kylcarbonyl, (C3-C 7) -Cycloal kylcarbonyl,
  • R 21 and R 22 are the same or different and independently of each other
  • R 23 is hydrogen, (Ci-C7) alkyl, (C 2 -C 7) alkenyl, (C 2 -C 7) alkynyl, (Ci-C7) -
  • R 24 is hydrogen, (Ci-C7) alkyl, (C 2 -C 7) alkenyl, (C 2 -C 7) alkynyl, (Ci-C7) -
  • R 1 , R 2 and R 7 independently of one another represent hydrogen, halogen, cyano, nitro,
  • X 1 , X 2 and X 3 are the same or different and are each independently O.
  • Grouping NR 20 are, but in no case adjacent to an O and S atom and in each case in each case more than one O or S atom in the formed 5-membered ring is contained, and wherein R 2 in the grouping CR 2 and R 20 in moiety NR 20 each have the same or different meanings according to the above or below definitions,
  • W is O (oxygen) or S (sulfur),
  • a 1 , A 2 , A 3 , A 4 and A 5 are the same or different and are independently N (nitrogen) or the group CR 7 , but in no case more than two N atoms are adjacent, and wherein R 7 in the grouping CR 7 each has identical or different meanings according to the above definition,
  • R 3 is (Ci-C 6) -alkyl, cyano- (Ci-C6) alkyl, (C 2 -C 6) alkenyl , (C 2 -C 6) alkynyl, (Ci-C 6) - haloalkyl, (C2-C6) haloalkenyl, (C2-C6) haloalkynyl, (C3-C6) -cycloalkyl, (C 3 -C 6) - halocycloalkyl, (C 4 -C 6) cycloalkenyl, (C 4 -C 6) -Halocycloalkenyl, aryl,
  • Haloalkylthio (C 1 -C 6 ) -alkyl, R 21 R 22 N- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) - alkyl,
  • R 4 represents hydrogen, (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) -alkynyl, (Ci-C 6) - haloalkyl, (C2-C6) - haloalkenyl, (C2-C6) haloalkynyl, (C3-C6) -cycloalkyl, (C 3 -C 6) -
  • Halocycloalkyl (C 4 -C 6) -cycloalkenyl, (C 4 -C 6) -halocycloalkenyl, aryl, aryl- (C 1 -C 6 ) -alkyl, heteroaryl, heteroaryl- (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) ) -cycloalkyl- (Ci-C 6) - alkyl, heterocyclyl, heterocyclyl (Ci-C 6) alkyl, (Ci-C6) alkoxy (Ci-C 6) alkyl,
  • R 5 and R 6 independently of one another represent hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (C 1 -C 6 ) -haloalkyl, (C 2 -C 6 ) haloalkenyl, (C2-C6) haloalkynyl, (C3-C6) -cycloalkyl, (C3-C 6) halocycloalkyl, (C-C6) cycloalkenyl, (C-C6) - Halocycloalkenyl, aryl, Aryl- (C 1 -C 6) -alkyl, heteroaryl, heteroaryl- (C 1 -C 6) -alkyl, (C 3 -C 6) -cycloalkyl (C 1 -C 6) -alkyl, heterocyclyl, heterocyclyl- (C 1 -
  • R 1 and X 1 when X 1 is a group CR 2 , with the atoms to which they are attached, a fully saturated, partially saturated or completely
  • X 1 and X 2 when both represent a group CR 2 , with the atoms to which they are attached form a fully saturated, partially saturated or fully unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring,
  • a 1 and A 2 when both represent a group CR 7 , with the atoms to which they belong
  • a 2 and A 3 when both represent a group CR 7 , with the atoms to which they belong
  • a 3 and A 4 when both represent a group CR 7 , with the atoms to which they belong
  • R 9, R 10, R 1 1, R 12, R 13, R 14, R 15, R 16, R 17, R 18 and R 19 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, (Ci-C 6) -alkyl, (C2-C6) alkenyl, (C 2 -C 6) - alkynyl, (Ci-C 6) -haloalkyl, (C2-C6) haloalkenyl, (C2-C6) haloalkynyl , (C 3 -C 6) - cycloalkyl, aryl, aryl (Ci-C 6) alkyl, heteroaryl, heteroaryl (Ci-C 6) alkyl, (C 3 -C 6) - cycloalkyl (Ci- C 6 ) -alkyl, heterocyclyl, heterocyclyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy (C 1
  • R 23 is hydrogen, (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) -alkynyl, (Ci-C 6) - cyanoalkyl, (Ci-C 6) - haloalkyl, (C2-C6) haloalkenyl, (C2-C6) haloalkynyl, (C 3 -C 6) -
  • R 24 is hydrogen, (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) -alkynyl, (Ci-C 6) - cyanoalkyl, (Ci-C 6) - haloalkyl, (C2-C6) haloalkenyl, (C2-C6) haloalkynyl, (C 3 -C 6) -
  • R 1 , R 2 and R 7 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine,
  • Thfluoromethoxymethyl thfluoromethoxyethyl, trifluoromethoxy-n-propyl
  • Methoxyethoxymethyl, methoxyethoxyethyl, methoxymethoxyethyl, ethoxy-n-propoxymethyl, ethoxy-n-propoxyethyl, ethoxyethoxymethyl, ethoxyethoxyethyl (C 2 -C 6 ) -haloalkenyl, (C 2 -C 6 ) -haloalkynyl, pentafluorothio, aryl- (C 1 -C 6 ) - alkyl, heteroaryl- (C 1 -C 6 ) -alkyl-heterocyclyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylcarbonyl- (C 1 -C 6 ) -alkyl, COOR 23 , CONR 21 R 22 , COR 23 , -C NOR 23 , R 21 R 22 N- (C 1 -C 6 )
  • Cycloalkylaminosulfonylannino, diazo, aryldiazo, trimethylsilyl, triethylsilyl, tris (iso-propyl) silyl, diphenyl (methyl) silyl, dimethyl (phenyl) silyl, dimethyl (tert-butyl) silyl, diphenyl (tert-butyl) silyl, X 1 , X 2 and X 3 are the same or different and are each independently O.
  • Grouping NR 20 are, but in no case adjacent to an O and S atom and in each case in each case more than one O or S atom in the formed 5-membered ring is contained, and wherein R 2 in the grouping CR 2 and R 20 in the grouping NR 20 are the same or different
  • W is O (oxygen) or S (sulfur)
  • a 1 , A 2 , A 3 , A 4 and A 5 are the same or different and independently of one another represent N (nitrogen) or the group CR 7 , but in none If more than two N atoms are adjacent, and R 7 in the group CR 7 has the same or different meanings as defined above,
  • R 3 is methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-
  • Methoxyethoxymethyl methoxyethoxyethyl, methoxymethoxyethyl, ethoxy-n-propoxymethyl, ethoxy-n-propoxyethyl, ethoxyethoxymethyl, ethoxyethoxyethyl, methoxyethoxy-n-propyl, ethoxyethoxy-n-propyl, cyclopropylmethyl,
  • Nonafluorobutyl chlorodifluoromethyl, bromodifluoromethyl, dichlorofluoromethyl, iododifluoromethyl, bromofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, fluoromethyl, difluoromethyl, 1,1-difluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 3,3,3- trifluoro-n-propyl, difluoro-tert-butyl, (C2-C6) haloalkenyl, (C2-C6) haloalkynyl, (C 3 -C 6) - cycloalkyl, (C3-C 6) halocycloalkyl, (C -C 6 ) -cycloalkenyl, (C -C 6 ) -halocycloalkenyl, aryl, aryl- (C 1
  • Trifluoromethoxymethyl trifluoromethoxyethyl, trifluoromethoxy-n-propyl,
  • Heteroatoms form interrupted and optionally further substituted 3-7-membered ring
  • R 1 and X 1 when X 1 is a group CR 2 , with the atoms to which they are attached, a fully saturated, partially saturated or completely
  • X 1 and X 2 when both represent a group CR 2 , with the atoms to which they belong
  • a 1 and A 2 when both represent a group CR 7 , with the atoms to which they belong
  • a 2 and A 3 when both represent a group CR 7 , with the atoms to which they belong
  • a 3 and A 4 when both represent a group CR 7 , with the atoms to which they belong
  • R 8, R 9, R 10, R 1 1, R 12, R 13, R 14, R 15, R 16, R 17, R 18 and R 19 independently of one another represent hydrogen, fluorine, methyl, ethyl, n-propyl , iso-propyl, n-butyl, isobutyl, tert-butyl, ethenyl, 1-propenyl, 2-propenyl, 1-methyl-ethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl 1 -propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl,
  • Difluoromethoxy-n-propyl 2,2-difluoroethoxymethyl, 2,2-difluoroethoxyethyl, 2,2-difluoroethoxy-n-propyl, 2,2,2-thfluoroethoxynethyl, 2,2,2-thfluoroethoxyethyl, 2,2,2- Thfluoroethoxy-n-propyl, pentafluoroethoxymethyl, pentafluoroethoxyethyl, pentafluoroethoxy-n-propyl, methylthiomethyl, methylthioethyl, ethylthioethyl, methylthio-n-propyl, ethylthio-n-propyl, trifluoromethylthiomethyl,
  • Bromodifluoromethyl dichlorofluoromethyl, iododifluoromethyl, bromofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, fluoromethyl, difluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 3,3,3-trifluoro-n-propyl, difluoro-tert.
  • R 1 , R 2 and R 7 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine,
  • X 1 , X 2 and X 3 are the same or different and are each independently O.
  • Grouping NR 20 are, but in no case adjacent to an O and S atom and in each case in each case more than one O or S atom in the formed 5-membered ring is contained, and wherein R 2 in the grouping CR 2 and R 20 in moiety NR 20 each have the same or different meanings according to the above or below definitions,
  • W is O (oxygen) or S (sulfur),
  • a 1 , A 2 , A 3 , A 4 and A 5 are the same or different and are independently N (nitrogen) or the group CR 7 , but in no case more than two N atoms are adjacent, and wherein R 7 in the group CR 7 has the same or different meanings as defined above,
  • R 5 and R 6 independently of one another represent hydrogen, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, n-pentyl, 1-methylbutyl, 2 Methylbutyl, 3-methylbutyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyanomethyl,
  • a 1 and A 2 when both represent a group CR 7 , with the atoms to which they are attached form a fully saturated, partially saturated or completely unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring,
  • a 2 and A 3 when both represent a group CR 7 , with the atoms to which they belong
  • a 3 and A 4 when both represent a group CR 7 , with the atoms to which they belong
  • Hydrogen methyl, ethyl, n -propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1 , 1-dimethylpropyl, 1, 2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2 Dimethylbutyl, 1, 3-di-methylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2-thmethylpropyl, 1, 2,2 Trimethylpropyl, 1-ethyl-1-
  • Difluoromethoxy-n-propyl 2,2-difluoroethoxymethyl, 2,2-difluoroethoxyethyl, 2,2-difluoroethoxy-n-propyl, 2,2,2-thfluoroethoxymethyl, 2,2,2-trifluoroethoxyethyl, 2,2,2- Trifluoroethoxy-n-propyl, pentafluoroethoxymethyl, pentafluoroethoxyethyl, pentafluoroethoxy-n-propyl, methylthiomethyl, methylthioethyl, ethylthioethyl, methylthio-n-propyl, ethylthio-n-propyl, trifluoromethylthiomethyl,
  • Methoxycarbonylmethyl ethoxycarbonylmethyl, n-propyloxycarbonylmethyl, isopropyloxycarbonylmethyl, tert-butyloxycarbonylmethyl,
  • Methoxycarbonylmethyl ethoxycarbonylmethyl, n-propyloxycarbonylmethyl, isopropyloxycarbonylmethyl, tert-butyloxycarbonylmethyl,
  • heteroaryl heteroaryl- (C 1 -C 6 ) -alkyl, heterocyclyl- (C 1 -C 6 ) -alkyl, NR 21 R 22 .
  • Particular preference is given to compounds of the general formula (I) which are described by (la) to (ly)
  • R 1 , R 2 and R 7 are independently hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, thiocyanato, isothiocyanato, methoxy, ethoxy, iso-propyloxy, methylsulfonyl, hydrothio, hydroxy, amino, imino, diazo, methyl , Ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, tert-butyl, cyclopropylmethyl, cyclopropyl, cyclobutyl, cyclopentyl, ethenyl, 1-propenyl, 2-propenyl, 1-methyl-ethenyl, methoxymethyl, Trifluoromethyl, pentafluoroethyl, chlorodifluoromethyl, difluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl
  • X 1 , X 2 and X 3 are the same or different and are each independently O.
  • Grouping NR 20 are, but in no case adjacent to an O and S atom and in each case in each case more than one O or S atom in the formed 5-membered ring is contained, and wherein R 2 in the grouping CR 2 and R 20 in the moiety NR 20 each have the same or different meanings according to the above or below definitions, W is O (oxygen) or S (sulfur),
  • a 1 , A 2 , A 3 , A 4 and A 5 are the same or different and are independently N (nitrogen) or the group CR 7 , but in no case more than two N atoms are adjacent, and wherein R 7 in the group CR 7 each have the same or different meanings according to the above
  • R 5 and R 6 independently of one another represent hydrogen, methyl, ethyl, n-propyl, 1 -
  • R 1 and X 1 when X 1 is a group CR 2 , with the atoms to which they are attached, a fully saturated, partially saturated or completely form unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring, and X 2 , when both represent a group CR 2 , with the atoms to which they are attached, a fully saturated, partially saturated or fully unsaturated, form optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring, and A 2 , when both represent a group CR 7 , with the atoms to which they are attached, a fully saturated, partially saturated or fully unsaturated, optionally Heteroatoms form interrupted and optionally further substituted 5-7 membered ring, and A 3 , when both represent a group CR 7 , with the atoms to which they are attached, a fully saturated, partially saturated or fully unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered n ring
  • Y is a bond or groups Y-1 to Y-2
  • R 9 R 10, R 1 1, R 12 and R 13 are independently hydrogen, methyl
  • R 5 and R 6 with the atom to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring, and
  • R 20 is hydrogen, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, cyclopropylmethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, heterocyclyl, methylcarbonyl, ethylcarbonyl, iso -propylcarbonyl, iso Butylcarbonyl, tert-butylcarbonyl, cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl, methoxycarbonyl, ethoxycarbonyl, tert-butyloxycarbonyl,
  • Residue definitions apply both to the end products of the general formula (I) and correspondingly to the starting material or preparation required in each case for the preparation
  • arylsulfonyl is optionally substituted phenylsulfonyl or optionally substituted polycyclic arylsulfonyl, here in particular optionally substituted naphthylsulfonyl, for example substituted by fluorine, chlorine, bromine, iodine, cyano, nitro, alkyl, haloalkyl, haloalkoxy, amino,
  • cycloalkylsulfonyl alone or as part of a chemical group - is optionally substituted Cycloalkylsulfonyl, preferably having 3 to 6 carbon atoms such as cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl or cyclohexylsulfonyl.
  • AI kylsulfonyl alone or as part of a chemical group - is straight-chain or branched alkylsulfonyl, preferably having 1 to 8, or having 1 to 6 carbon atoms, for example (but not limited to) (Ci- C6) alkylsulfonyl as Methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, 1,1-dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methyl-butylsulfonyl, 1, 1 Dimethylpropylsulphonyl, 1, 2-dimethylpropylsulfonyl, 1, 2-
  • substituted polycyclic heteroarylsulfonyl here in particular optionally substituted quinolinylsulfonyl, for example substituted by fluorine, chlorine, bromine, iodine, cyano, nitro, alkyl, haloalkyl, haloalkoxy, amino, alkylamino,
  • Alkylcarbonylamino, dialkylamino or alkoxy groups Alkylcarbonylamino, dialkylamino or alkoxy groups.
  • alkylthio alone or as part of a chemical group - represents straight-chain or branched S-alkyl, preferably having 1 to 8, or having 1 to 6 carbon atoms, such as (C 1 -C 10) -, (C 1 -C 6) - or (C 1 -C 4 ) -alkylthio, for example (but not limited to) (C 1 -C 6) -alkylthio, such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1, 1-dimethylethyl thio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1, 1-dimethylpropylthio, 1, 2-dimethylpropylthio, 2,2-dimethylpropylthio, 1-ethylprop
  • alkenylthio means an alkenyl radical bonded via a sulfur atom
  • alkynylthio means an alkynyl radical bonded via a sulfur atom
  • cycloalkylthio means a cycloalkyl radical bonded via a sulfur atom
  • cycloalkenylthio means a cycloalkenyl radical bonded via a sulfur atom
  • alkylsulfinyl such as methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1, 1-dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl, 2 Methylbutylsulfinyl, 3-methylbutylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethyl-propylsulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl
  • alkenylsulfonyl and alkynylsulfonyl are defined according to the invention as alkenyl or alkynyl radicals which are linked to the skeleton via -S (OO) 2, such as (C 2 -C 10) -, (C 2 -C 6 ) - or (C 2 -) C) -alkenylsulfonyl or (C 3 -C 10) -, (C 3 -C 6 ) - or (C 3 -C) -alkynylsulfonyl.
  • -S (OO) 2 such as (C 2 -C 10) -, (C 2 -C 6 ) - or (C 2 -) C) -alkenylsulfonyl or (C 3 -C 10) -, (C 3 -C 6 ) - or (C 3 -C) -alkynylsulfonyl.
  • Alkoxy means an alkyl radical bonded through an oxygen atom, for example (but not limited to) (C 1 -C 6) -alkoxy, such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1 , 1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1, 1-dimethylpropoxy, 1, 2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2 Methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1, 1-dimethylbutoxy, 1, 2-dimethylbutoxy, 1, 3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1 ethyl butoxy, 2-ethylbutoxy, 1, 1, 2-trimethylpropoxy, 1, 2,2-trimethylpropoxy, 1-ethyl
  • Oxygen atom bound alkenyl radical, alkynyloxy means one over one
  • Alkoxy-bonded alkynyl such as (C 2 -C 10) -, (C 2 -C 6) - or (C 2 -C 4 ) -alkenoxy or (C 3 -C 10) -, (Cs-Ce) - or (C 3 -C) -alkynoxy ,
  • Cycloalkyloxy denotes a cycloalkyl radical bonded via an oxygen atom and cycloalkenyloxy denotes a cycloalkenyl radical bonded via an oxygen atom.
  • alkenylcarbonyl and “alkynylcarbonyl” are, unless otherwise defined elsewhere, according to the invention for alkenyl or alkynyl radicals which are bonded to the skeleton via -C (OO) -, such as (C 2 -C 10) -, ( C 2 -C 6) - or (C 2 -C 4 ) -alkenylcarbonyl or (C 2 -C 10) -, (C 2 -C 6) - or (C 2 -C 4 ) -alkynylcarbonyl.
  • the number of C atoms refers to the alkenyl or alkynyl radical in the alkenyl or alkynylcarbonyl group.
  • Alkoxycarbonyl (alkyl-OC ( O) -), unless otherwise defined elsewhere:
  • the number of C atoms refers to the alkyl radical in the alkoxycarbonyl group.
  • alkenyloxycarbonyl and “alkynyloxycarbonyl” are, unless otherwise defined elsewhere, according to the invention for alkenyl or alkynyl radicals which are bonded to the skeleton via -O-C (OO) -, such as (C 2 -C 10) - , (C 2 -C 6) - or (C 2 -C 4 ) -alkenyloxycarbonyl or (C 3 -C 10) -, (C 3 -C 6) - or (C 3 -C 4 ) -alkynyloxycarbonyl.
  • the number of C atoms refers to the alkenyl or alkynyl radical in the alkene or
  • the number of carbon atoms refers to the alkyl radical in the alkylcarbonyloxy group.
  • alkenylcarbonyloxy and “alkynylcarbonyloxy” are defined according to the invention as alkenyl or alkynyl radicals which are bonded to the skeleton via (-C (OO) -O-), such as (C 2 -C 10) -, (C 2 -C 4) -C 6) - or (C 2 -C 4 ) -alkenylcarbonyloxy or (C 2 -C 10) -, (C 2 -C 6) - or (C 2 -C 4 ) -alkynylcarbonyloxy.
  • the number of C atoms refers to the alkenyl or alkynyl radical in the alkenyl or alkynylcarbonyloxy group.
  • aryl means an optionally substituted mono-, bi- or
  • polycyclic aromatic system having preferably 6 to 14, in particular 6 to 10 ring C atoms, for example phenyl, naphthyl, anthryl, phenanthrenyl, and the like, preferably phenyl.
  • optionally substituted aryl also includes polycyclic systems, such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenylyl, the binding site being on the aromatic system.
  • Aryl is also generally known from the term “optionally substituted phenyl ".
  • Preferred aryl substituents here are, for example, hydrogen, halogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, halocycloalkyl, alkenyl, alkynyl, aryl,
  • heterocyclyl or heterocyclic ring is optionally substituted, it may be fused with other carbocyclic or heterocyclic rings.
  • heterocyclic ring preferably contains 3 to 9 ring atoms, especially 3 to 6
  • Ring atoms, and one or more, preferably 1 to 4, in particular 1, 2 or 3 heteroatoms in the heterocyclic ring, preferably from the group N, O, and S, but not two oxygen atoms should be directly adjacent, as
  • 3-membered and 4-membered heterocycles are, for example, 1- or 2-aziridinyl, oxiranyl, thiiranyl, 1- or 2- or 3-azetidinyl, 2- or 3-oxetanyl, 2- or 3-thietanyl, 1,3 -Dioxetan-2-yl.
  • Heterocyclyl are a partially or fully hydrogenated heterocyclic radical having two heteroatoms from the group N, O and S, such as 1- or 2- or 3- or 4-pyrazolidinyl; 4,5-dihydro-3H-pyrazole-3 or 4 or 5-yl; 4,5-dihydro-1H-pyrazole-1 - or 3- or 4- or 5-yl; 2,3-dihydro-1H-pyrazole-1 - or 2- or 3- or 4- or 5-yl; 1- or 2- or 3- or 4-imidazolidinyl; 2,3-dihydro-1H-imidazole-1 - or 2- or 3- or 4-yl; 2,5-dihydro-1H-imidazole-1 - or 2- or 4- or 5-yl; 4,5-dihydro-1H-imidazole-1 - or 2- or 4- or 5-yl; Hexahydropyridazine-1 - or 2- or 3- or
  • heterocyclyl are a partially or fully hydrogenated heterocyclic radical having 3 heteroatoms from the group N, O and S, such as, for example, 1, 4,2-dioxazolidin-2 or 3 or 5-yl; 1, 4,2-dioxazol-3 or 5-yl;
  • heterocycles listed above are preferably, for example, hydrogen, halogen, alkyl, haloalkyl, hydroxy, alkoxy, cycloalkoxy, aryloxy, alkoxyalkyl,
  • Suitable substituents for a substituted heterocyclic radical are the substituents mentioned below, in addition to oxo and thioxo.
  • Oxo group as a substituent on a ring C atom then means, for example, a carbonyl group in the heterocyclic ring.
  • lactones and lactams are preferably also included.
  • the oxo group may also be attached to the hetero ring atoms, which may exist in different oxidation states, e.g. in the case of N and S, for example, the divalent groups N (O), S (O) (also SO for short) and S (O) 2 (also SO2 for short) occur and form in the heterocyclic ring.
  • N and S for example, the divalent groups N (O), S (O) (also SO for short) and S (O) 2 (also SO2 for short) occur and form in the heterocyclic ring.
  • -N (O) and -S (O) groups both enantiomers are included.
  • heteroaryl is heteroaromatic
  • Heteroaryls of the invention are, for example, 1H-pyrrol-1-yl; 1H-pyrrol-2-yl; 1H-pyrrol-3-yl; Furan-2-yl; Furan-3-yl; Thien-2-yl; Thien-3-yl, 1H-imidazole-1-yl; 1 H-imidazol-2-yl; 1 H -imidazol-4-yl; 1 H -imidazol-5-yl; 1H-pyrazole-1-yl; 1H-pyrazol-3-yl; 1H-pyrazol-4-yl; 1 H-pyrazol-5-yl, 1 H-1, 2,3-triazol-1-yl, 1 H-1, 2,3-triazol-4-yl, 1 H-1, 2,3-triazole 5-yl, 2H-1, 2,3-triazol-2-yl, 2H-1,2,3-triazol-4-yl, 1H-1, 2,4-triazol-1-yl
  • heteroaryl groups according to the invention may furthermore be substituted by one or more identical or different radicals. If two adjacent carbon atoms are part of another aromatic ring, they are fused heteroaromatic systems, such as benzo-fused or multiply fused heteroaromatics.
  • quinolines for example quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl
  • Isoquinolines e.g., isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl, isoquinolin-8-yl
  • quinoxaline for example quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl
  • quinoxaline e.g., isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-
  • quinazoline cinnoline; 1,5-naphthyridine; 1,6-naphthyridine; 1,7-naphthyridine; 1,8-naphthyridine; 2,6-naphthyridine; 2,7-naphthyridine; phthalazine; Pyridopyrazine;
  • heteroaryl are also 5- or 6-membered benzo-fused rings from the group 1H-indol-1-yl, 1H-indol-2-yl, 1H-indol-3-yl, 1H-indole-4 yl, 1H-indol-5-yl, 1H-indol-6-yl, 1H-indol-7-yl, 1-benzofuran-2-yl, 1-benzofuran-3-yl, 1-benzofuran-4 -yl, 1-benzofuran-5-yl, 1-benzofuran-6-yl, 1-benzofuran-7-yl, 1-benzothiophen-2-yl, 1-benzothiophen-3-yl, 1-benzothiophen-4-yl , 1-benzothiophene-5-yl, 1-benzothiophene
  • halogen means, for example, fluorine, chlorine, bromine or iodine.
  • halogen means, for example, a fluorine, chlorine, bromine or iodine atom.
  • alkyl means a straight-chain or branched, open-chain, saturated hydrocarbon radical which is optionally monosubstituted or polysubstituted and is referred to in the latter case as “substituted alkyl".
  • Substituents are halogen atoms, alkoxy, haloalkoxy, cyano, alkylthio,
  • Haloalkylthio, amino or nitro groups particularly preferred are methoxy, methyl, fluoroalkyl, cyano, nitro, fluorine, chlorine, bromine or iodine.
  • the prefix "bis" also includes the combination of different alkyl radicals, for example, methyl (ethyl) or
  • Polyhaloalkyl such as CH 2 CHFCI, CF 2 CCIFH, CF 2 CBrFH, CH 2 CF 3 ;
  • perhaloalkyl also encompasses the term perfluoroalkyl.
  • Partially fluorinated alkyl means a straight-chain or branched, saturated
  • Hydrocarbon which is mono- or polysubstituted by fluorine, wherein the corresponding fluorine atoms as substituents on one or more
  • Hydrocarbon chain can be located, such as. B. CHFCH3, CH 2 CH 2 F, CH 2 CH 2 CF 3, CHF 2, CH 2 F, CF 3 CHFCF 2
  • Partially fluorinated haloalkyl means a straight-chain or branched, saturated hydrocarbon which is substituted by various halogen atoms having at least one fluorine atom, all other optionally present
  • Halogen atoms are selected from the group fluorine, chlorine or bromine, iodine.
  • the corresponding halogen atoms may be present as substituents on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain.
  • Partially fluorinated haloalkyl also includes the
  • Haloalkoxy is eg OCF 3 , OCHF 2 , OCH 2 F, OCF 2 CF 3 , OCH 2 CF 3 and OCH 2 CH 2 Cl;
  • (C 1 -C 4 ) -alkyl given here by way of example means a
  • Carbon atoms corresponding to the range for C atoms, d. H. includes the radicals methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl.
  • General alkyl radicals having a larger specified range of carbon atoms eg. As "(Ci-C6) alkyl", accordingly also include straight-chain or branched alkyl radicals having a larger number of C atoms, d. H. according to example, the alkyl radicals with 5 and 6 carbon atoms.
  • hydrocarbon radicals such as alkyl, alkenyl and alkynyl radicals, even in assembled radicals, are lower
  • Carbon skeletons e.g. with 1 to 6 C atoms or with unsaturated groups having 2 to 6 C atoms, preferred.
  • Alkyl radicals also in the assembled radicals such as alkoxy, haloalkyl, etc., mean e.g.
  • Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals, wherein at least one double bond or triple bond is contained. Preference is given to radicals having a double bond or triple bond.
  • alkenyl also includes straight-chain or branched open-chain hydrocarbon radicals having more than one double bond, such as 1,3-butadienyl and 1,4-pentadienyl, but also allenyl or cumulenyl radicals having one or more cumulative double bonds, such as For example, allenyl (1,2-propadienyl), 1,2-butadienyl and 1,2,3-pentatrienyl.
  • alkenyl means, for example, vinyl, which may optionally be substituted by further alkyl radicals, for example (but not
  • (C 2 -C 6) alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1 -propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl , 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3 - Methyl 3-butenyl, 1, 1-dimethyl-2-propenyl, 1, 2-dimethyl-1-propenyl, 1, 2-dimethyl-2-propenyl, 1-ethyl-1-propen
  • alkynyl in particular also includes straight-chain or branched open-chain hydrocarbon radicals having more than one triple bond or else having one or more triple bonds and one or more double bonds, for example 1,3-butatrienyl or 3-penten-1-yn-1 -yl.
  • (C 2 -C 6) -alkynyl is, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4 pentynyl, 2-methyl-3-pentynyl,
  • cycloalkyl means a carbocyclic, saturated ring system preferably having 3-8 ring C atoms, eg cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, which is optionally further substituted, preferably by hydrogen, alkyl, alkoxy, cyano, nitro, alkylthio , Haloalkylthio, halogen, alkenyl, alkynyl,
  • Cycloalkyl, z As an alkylidene group such as methylidene, are included.
  • optionally substituted cycloalkyl it also encompasses polycyclic aliphatic systems such as, for example, bicyclo [1, 1] -butan-1-yl, bicyclo [1, 1] -butan-2-yl, bicyclo [2.1.0] pentane 1 -yl, bicyclo [1 .1 .1] pentan-1-yl, bicyclo [2.1.0] pentan-2-yl,
  • (C 3 -C 7) -cycloalkyl means a
  • substituted cycloalkyl are also spirocyclic aliphatic
  • Cycloalkenyl means a carbocyclic, non-aromatic, partially unsaturated ring system preferably having 4-8 C atoms, for example 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2-
  • Alkylidene group such as methylidene, are included. In case of if necessary
  • Cycloalkylidene means a carbocyclic radical which is bonded via a double bond. If the compounds can form tautomers by hydrogen shift which would not be structurally formally recognized by the formula (I), these tautomers are nevertheless encompassed by the definition of the compounds of the formula (I) according to the invention, unless a particular tautomer is the subject of
  • the compounds of the general formula (I) can exist as stereoisomers.
  • the possible stereoisomers defined by their specific spatial form, such as enantiomers, diastereomers, Z and E isomers, are all encompassed by the formula (I). If, for example, one or more alkenyl groups are present, diastereomers (Z and E isomers) can occur. For example, if one or more asymmetric carbon atoms are present, enantiomers and diastereomers may occur.
  • Stereoisomers can be obtained from the resulting mixtures in the preparation by conventional separation methods. The chromatographic separation can be used both on an analytical scale for
  • stereoisomers can be selectively prepared by using stereoselective reactions using optically active sources and / or adjuvants.
  • the invention thus also relates to all stereoisomers which comprises the general formula (I) but are not specified with their specific stereoform, and mixtures thereof.
  • Substituted heteroarylcarboxylic acid hydrazides of the general formula (I) can be prepared by known processes (see Tetrahedron 2003, 59, 7733;
  • Heteroarylcarbonklaren and Heteroarylcarbonklarechloriden The optionally further substituted heteroarylcarboxylic acid in question is converted into the corresponding by means of a suitable chlorinating agent (for example oxalyl chloride or thionyl chloride) in an aprotic solvent (for example toluene)
  • a suitable chlorinating agent for example oxalyl chloride or thionyl chloride
  • an aprotic solvent for example toluene
  • Heteroarylcarbonklarechlorid transferred, if this is not commercially available, and this then with a corresponding 1, 1 'disubstituted hydrazine using a suitable base (eg triethylamine (EtsN)), di-iso-propylethylamine) in a suitable polar aprotic solvent ( For example, tetrahydrofuran (THF) or dichloromethane (DCM)) to a Heteroarylcarbonsaurehydrazid (A) implemented.
  • a suitable base eg triethylamine (EtsN)
  • EtsN triethylamine
  • DCM dichloromethane
  • the optionally further substituted heteroarylcarboxylic acid hydrazide (A) can also be prepared by a direct reaction with suitable reagents (eg 1-hydroxybenzotriazoles (HOBt), N- (3-dimethylaminopropyl) -N'-ethylcarbodiimide hydrochloride (EDC) or 2,4, 6-Tripropyl- 1, 3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide (T3P) together with a suitable base such as triethylamine or di-iso-propylethylamine) mediated coupling of an optionally further substituted heteroarylcarboxylic with a corresponding 1, 1 'disubstituted hydrazine in a suitable polar aprotic solvent (eg dichloromethane, acetonitrile or tetrahydrofuran) are prepared.
  • suitable polar aprotic solvent eg dichloromethane, ace
  • Step is the optionally further substituted heteroarylcarboxylic (A) using an appropriately substituted arylalkyl halide or
  • Heteroarylalkyl halide and a suitable base e.g., sodium hydride or
  • Triethylamine (EtsN)) in a suitable solvent (e.g., tetrahydrofuran, N, N-dimethylformamide (DMF) or dichloromethane) into a substituted solvent
  • a suitable solvent e.g., tetrahydrofuran, N, N-dimethylformamide (DMF) or dichloromethane
  • Substituted heteroarylcarboxylic acid hydrazides of the general formula (I) can alternatively also be prepared via the reduction of hydrazones (B), provided that the radical R 6 is hydrogen. In the course of this synthesis sequence becomes
  • Heteroarylcarbonklare hydrazide (I) is transferred (Scheme 2).
  • R 1 , R 3 , R 4 and R 5 and A 1 , A 2 , A 3 , A 4 , A 5 , X 1 , X 2 , X 3 and Y have the meanings defined above and W is exemplified, but not limiting in scheme 2 below for oxygen.
  • Unsymmetrically substituted heteroarylcarboxylic acid hydrazides (I) can also be prepared on the second hydrazide nitrogen (NR 3 R 4 ) using tert-butyl 1-methylhydrazinecarboxylate (Scheme 3). The person in question
  • Heteroarylcarboxylic acid chloride if not commercially available, and thereafter with tert-butyl-1-methylhydrazinecarboxylate using a suitable base (e.g., triethylamine (EtsN)), di-iso -propylethylamine) in one
  • a suitable base e.g., triethylamine (EtsN)
  • EtsN triethylamine
  • di-iso -propylethylamine di-iso -propylethylamine
  • polar aprotic solvents e.g., tetrahydrofuran (THF) or
  • the optionally further substituted heteroarylcarboxylic acid hydrazide (D) can also be prepared by a direct reaction with suitable reagents (eg 1-hydroxybenzotriazoles (HOBt), N- (3-dimethylaminopropyl) -N'-ethylcarbodiimide hydrochloride (EDC) or 2,4, 6-Tripropyl- 1, 3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide (T3P) together with a suitable base such as triethylamine or di-iso-propylethylamine) mediated coupling of an optionally further substituted heteroarylcarboxylic with tert-butyl-1 - methylhydrazinecarboxylate in a suitable polar aprotic solvent (eg
  • Heteroarylalkylhalogenids and a suitable base for example, sodium hydride or Triethylamine (EtsN)
  • a suitable solvent eg tetrahydrofuran, N, N-dimethylformamide (DMF) or dichloromethane
  • Heteroarylcarboxylic acid hydrazide (If) with a suitable acid e.g.
  • Trifluoroacetic acid in a polar aprotic solvent (e.g., dichloromethane) to the N-mono-substituted heteroarylcarboxylic acid hydrazide (Ie).
  • a suitable alkyl halide e.g., ethyl iodide in Scheme 3 below
  • a suitable base e.g., sodium hydride or potassium carbonate
  • R 1 , R 5 and R 6 and A 1 , A 2 , A 3 , A 4 , A 5 , X 1 , X 2 , X 3 and Y have the meanings defined above, R 3 is exemplary but not limiting, in the following scheme 3 for methyl and W is exemplified, but not limiting, for
  • Example numbers correspond to the numbers given in Tables A1 to G7 below.
  • Triethylamine (1: 3 equiv) in dichloromethane (2 ml / mmol) was added under argon.
  • the resulting reaction mixture was stirred for 30 minutes at room temperature and then treated with water and dichloromethane.
  • the aqueous phase was repeatedly extracted intensively with dichloromethane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated.
  • Final purification by column chromatography of the resulting crude product afforded the isolation of 5-fluoro-N ', N', 1-trimethyl-3- (trifluoromethyl) -1H-pyrazole-4-carbohydrazide as a colorless solid.
  • Tetrahydrofuran (5 ml) was dissolved under argon and treated at room temperature with sodium hydride (41 mg, 1 .03 mmol, 60% pure). After stirring for 30 minutes
  • Tetrahydrofuran (5 ml) was dissolved under argon and treated at room temperature with sodium hydride (63 mg, 1 .59 mmol, 60% pure). After stirring for 30 minutes

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Abstract

The invention relates to substituted heteroaryl carboxylic acid hydrazides of general formula (I) or salts thereof, wherein the groups of formula (I) have the definitions stated in the description, for increasing the stress tolerance in plants with respect to abiotic stress, and also for strengthening plant growth and/or for increasing plant yield.

Description

Substituierte Heteroarylcarbonsaurehydrazide oder deren Salze und ihre Verwendung zur Steigerung der Stresstoleranz in Pflanzen.  Substituted Heteroarylcarbonsaurehydrazide or their salts and their use for increasing the stress tolerance in plants.
Beschreibung description
Die Erfindung betrifft substituierte Heteroarylcarbonsaurehydrazide oder deren Salze und ihre Verwendung zur Steigerung der Stresstoleranz in Pflanzen gegenüber abiotischem Stress, sowie zur Steigerung des Pflanzenwachstums und/oder zur Erhöhung des Pflanzenertrags. The invention relates to substituted Heteroarylcarbonsaurehydrazide or their salts and their use for increasing the stress tolerance in plants to abiotic stress, and to increase plant growth and / or to increase the plant yield.
Es ist bekannt, dass bestimmte substituierte Azinylcarboxamide, wie beispielsweise substituierte 4-(Trifluoromethyl)nicotinamide, Insektizide Eigenschaften besitzen (vgl. z. B. EP185256, WO2001/014373, WO2002/022583, JP07010841 , JP07025853, WO2005/1 13553). N-substituierte Azinylalkylazincarboxamide und ihre Insektizide Wirkung sind in DE102008041214 beschrieben, wobei als N-Substituenten der betreffenden Amide beispielsweise Alkyl-, Arylcarbonyl-, Alkylcarbonyl-, It is known that certain substituted azinylcarboxamides, such as, for example, substituted 4- (trifluoromethyl) nicotinamides, possess insecticidal properties (cf., for example, EP185256, WO2001 / 014373, WO2002 / 022583, JP07010841, JP07025853, WO2005 / 1 13553). N-substituted Azinylalkylazincarboxamide and their insecticidal activity are described in DE102008041214, wherein as N-substituents of the amides in question, for example, alkyl, arylcarbonyl, alkylcarbonyl,
Alkoxycarbonyl- und Arylsulfonylgruppen beschrieben werden, jedoch keine Alkoxycarbonyl and arylsulfonyl groups, but none
Aminosubstituenten, die zu Hydrazidstrukturen führen. Es ist weiter bekannt, daß bestimmte N-Alkoxy-substituierte Heteroarylcarboxamide als Wirkstoffe zur Steigerung des Pflanzenertrags und zur Steigerung gegen abiotischen Pflanzenstress eingesetzt werden können (vgl. WO2013/167651 ).  Amino substituents that lead to hydrazide structures. It is further known that certain N-alkoxy-substituted heteroarylcarboxamides can be used as active ingredients for increasing the plant yield and for increasing abiotic plant stress (compare WO2013 / 167651).
Die Herstellung von acylierten Hydraziden durch Reduktion von Hydrazonen wird in Tetrahedron, 2003, 59, 773 sowie in IT2000/MI0292 beschrieben, während in J. Org. Chem. 1975, 40, 19 photochemische Reaktionen von Benzoyl- und Acetylhydraziden beschrieben werden. Die Umsetzung von 1 ,1 -Dibenzoyl-2,2-dimethylhydrazin mit Hydrid-Reagenzien ist aus J. Org. Chem. 1956, 21 , 1 177 bekannt, während die durch Raney Nickel vermittelte Hydrogenolyse der Stickstoff-Stickstoffbindung in The preparation of acylated hydrazides by reduction of hydrazones is described in Tetrahedron, 2003, 59, 773 and in IT2000 / MI0292, while in J. Org. Chem. 1975, 40, 19 photochemical reactions of benzoyl and acetylhydrazides are described. The reaction of 1,1-dibenzoyl-2,2-dimethylhydrazine with hydride reagents is known from J. Org. Chem. 1956, 21, 177, while the hydrogenolysis of the nitrogen-nitrogen bond mediated by Raney nickel in
Acylhydrazinen in J. Org. Chem. 1957, 22, 148 beschrieben wird. 1 -Acyl- und 1 ,1 - Diacyl-2,2-dimethylhydrazine sind weiterhin aus Org. Preparations and Procedures 1970, 2, 275 bekannt. Ausgewählte substituierte cyclische Benzoylhydrazide werden im Rahmen von Studien zur Verwendung von RAMP- und SAMP-Hydrazonen in asymmetrischen organischen Synthesen beschrieben, z. B. in Turkish J Org. Chem. 2013, 37, 492-518, in Org. Lett.2001 , 3, 1575-1577 und in Tetrahedron Lett. 1995, 36, 6709-4712. Es ist ebenfalls bekannt, daß spezielle hochsubstituierte Morpholin- basierte Hydrazide als Chemokinrezeptor-Modulatoren verwendet werden können (vgl. WO2008/1 12156). Acylhydrazines are described in J. Org. Chem. 1957, 22, 148. 1-acyl and 1, 1-diacyl-2,2-dimethylhydrazine are further known from Org. Preparations and Procedures 1970, 2, 275. Selected substituted cyclic benzoylhydrazides have been reported in studies of the use of RAMP and SAMP hydrazones in asymmetric organic syntheses described, for. In Turkish J Org. Chem. 2013, 37, 492-518, in Org. Lett.2001, 3, 1575-1577 and in Tetrahedron Lett. 1995, 36, 6709-4712. It is also known that specific highly substituted morpholine-based hydrazides can be used as chemokine receptor modulators (see WO 2008/112156).
Es ist bekannt, dass Pflanzen auf natürliche Stressbedingungen, wie beispielsweise Kälte-, Hitze-, Trockenstress (Stress verursacht durch Trockenheit und/oder It is known that plants are susceptible to natural stress conditions, such as cold, heat, drought stress (stress caused by dryness and / or
Wassermangel), Verwundung, Pathogenbefall (Viren, Bakterien, Pilze, Insekten) etc. aber auch auf Herbizide mit spezifischen oder unspezifischen Abwehrmechanismen reagieren können [Pflanzenbiochemie, S. 393-462 , Spektrum Akademischer Verlag, Heidelberg, Berlin, Oxford, Hans W. Heidt, 1996.; Biochemistry and Molecular Biology of Plants, S. 1 102-1203, American Society of Plant Physiologists, Rockville, Maryland, eds. Buchanan, Gruissem, Jones, 2000]. Lack of water), wounding, pathogen infestation (viruses, bacteria, fungi, insects) etc. but also can react to herbicides with specific or nonspecific defense mechanisms [Plant Biochemistry, pp. 393-462, Spektrum Akademischer Verlag, Heidelberg, Berlin, Oxford, Hans W. Heidt, 1996; Biochemistry and Molecular Biology of Plants, p. 1 102-1203, American Society of Plant Physiologists, Rockville, Maryland, eds. Buchanan, Gruissem, Jones, 2000].
In Pflanzen sind zahlreiche Proteine und die sie codierenden Gene bekannt, die an Abwehrreaktionen gegen abiotischen Stress (z.B. Kälte, Hitze, Trockenheit, Salz, Überflutung) beteiligt sind. Diese gehören teilweise zu Signaltransduktionsketten (z.B. Transkriptionsfaktoren, Kinasen, Phosphatasen) oder bewirken eine physiologische Antwort der Pflanzenzelle (z.B. lonentransport, Entgiftung reaktiver Sauerstoff- Spezies). Zu den Signalkettengenen der abiotischen Stressreaktion gehören u.a. In plants, numerous proteins and the genes encoding them are involved, which are involved in abiotic stress defense reactions (e.g., cold, heat, drought, salt, flooding). These partially belong to signal transduction chains (e.g., transcription factors, kinases, phosphatases) or cause a physiological response of the plant cell (e.g., ion transport, detoxification of reactive oxygen species). The signal chain genes of the abiotic stress reaction include, among others.
Transkriptionsfaktoren der Klassen DREB und CBF (Jaglo-Ottosen et al., 1998, Science 280: 104-106). An der Reaktion auf Salzstress sind Phosphatasen vom Typ ATPK und MP2C beteiligt. Ferner wird bei Salzstress häufig die Biosynthese von Osmolyten wie Prolin oder Sucrose aktiviert. Beteiligt sind hier z.B. die Sucrose- Synthase und Prolin-Transporter (Hasegawa et al., 2000, Annu Rev Plant Physiol Plant Mol Biol 57: 463-499). Die Stressabwehr der Pflanzen gegen Kälte und Transcription factors of classes DREB and CBF (Jaglo-Ottosen et al., 1998, Science 280: 104-106). The response to salt stress involves phosphatases of the ATPK and MP2C types. Furthermore, in salt stress the biosynthesis of osmolytes such as proline or sucrose is often activated. Involved here are e.g. sucrose synthase and proline transporters (Hasegawa et al., 2000, Annu Rev Plant Physiol Plant Mol. Biol. 57: 463-499). The stress control of plants against cold and
Trockenheit benutzt z.T. die gleichen molekularen Mechanismen. Bekannt ist die Akkumulation von sogenannten Late Embryogenesis Abundant Proteins (LEA- Proteine), zu denen als wichtige Klasse die Dehydrine gehören (Ingram and Bartels, 1996, Annu Rev Plant Physiol Plant Mol Biol 47: 277-403, Close, 1997, Physiol Plant 700: 291 -296). Es handelt sich dabei um Chaperone, die Vesikel, Proteine und Dryness used z.T. the same molecular mechanisms. The accumulation of so-called Late Embryogenesis Abundant Proteins (LEA proteins), which include dehydrins as an important class, is known (Ingram and Bartels, 1996, Annu Rev Plant Physiol Plant Mol Biol 47: 277-403, Close, 1997, Physiol Plant 700: 291-296). These are chaperones, the vesicles, proteins and
Membranstrukturen in gestressten Pflanzen stabilisieren (Bray, 1993, Plant Physiol 103: 1035-1040). Außerdem erfolgt häufig eine Induktion von Aldehyd- Deydrogenasen, welche die bei oxidativem Stress entstehenden reaktiven Sauerstoff- Spezies (ROS) entgiften (Kirch et al., 2005, Plant Mol Biol 57: 315-332). Stabilize membrane structures in stressed plants (Bray, 1993, Plant Physiol 103: 1035-1040). In addition, induction of aldehyde De-dehydrogenases which detoxify the reactive oxygen species (ROS) produced by oxidative stress (Kirch et al., 2005, Plant Mol Biol 57: 315-332).
Heat Shock Faktoren (HSF) und Heat Shock Proteine (HSP) werden bei Hitzestress aktiviert und spielen hier als Chaperone eine ähnliche Rolle wie die Dehydrine bei Kälte- und Trockenstress (Yu et al., 2005, Mol Cells 19: 328-333). Heat Shock Factors (HSF) and Heat Shock Proteins (HSP) are activated by heat stress and act as chaperones in a similar role to dehydrins in cold and dry stress (Yu et al., 2005, Mol Cells 19: 328-333).
Eine Reihe von pflanzenendogenen Signalstoffen, die in die Stresstoleranz bzw. die Pathogenabwehr involviert sind, sind bereits bekannt. Zu nennen sind hier A number of plant endogenous signaling substances involved in stress tolerance and pathogen defense are already known. To call here are
beispielsweise Salicylsäure, Benzoesäure, Jasmonsäure oder Ethylen [Biochemistry and Molecular Biology of Plants, S. 850-929, American Society of Plant Physiologists, Rockville, Maryland, eds. Buchanan, Gruissem, Jones, 2000]. Einige dieser for example, salicylic acid, benzoic acid, jasmonic acid or ethylene [Biochemistry and Molecular Biology of Plants, pp. 850-929, American Society of Plant Physiologists, Rockville, Maryland, eds. Buchanan, Gruissem, Jones, 2000]. Some of these
Substanzen oder deren stabile synthetische Derivate und abgeleitete Strukturen sind auch bei externer Applikation auf Pflanzen oder Saatgutbeizung wirksam und aktivieren Abwehrreaktionen, die eine erhöhte Stress- bzw. Pathogentoleranz der Pflanze zur Folge haben [Sembdner, and Parthier, 1993, Ann. Rev. Plant Physiol. Plant Mol. Biol. 44: 569-589]. Substances or their stable synthetic derivatives and derived structures are also effective in external application to plants or seed dressing and activate defense reactions that result in an increased stress or pathogen tolerance of the plant [Sembdner, and Parthier, 1993, Ann. Rev. Plant Physiol. Plant Mol. Biol. 44: 569-589].
Es ist weiter bekannt, dass chemische Substanzen die Toleranz von Pflanzen gegen abiotischen Stress erhöhen können. Derartige Substanzen werden dabei entweder durch Saatgut-Beizung, durch Blattspritzung oder durch Bodenbehandung appliziert. So wird eine Erhöhung der abiotischen Stresstoleranz von Kulturpflanzen durch Behandlung mit Elicitoren der Systemic Acquired Resistance (SAR) oder It is also known that chemical substances can increase the tolerance of plants to abiotic stress. Such substances are applied either by seed dressing, by foliar spraying or by soil treatment. Thus, increasing the abiotic stress tolerance of crops by treatment with systemic acquired resistance (SAR) or
Abscisinsäure-Derivaten beschrieben (Schading and Wei, WO2000/28055; Abrams and Gusta, US5201931 ; Abrams et al, WO97/23441 , Churchill et al., 1998, Plant Growth Regul 25: 35-45). Desweiteren wurden Effekte von Wachstumsregulatoren auf die Stresstoleranz von Kulturpflanzen beschrieben (Morrison and Andrews, 1992, J Plant Growth Regul 11: 1 13-1 17, RD-259027). In diesem Zusammenhang ist ebenfalls bekannt, dass ein wachstumsregulierendes Naphthylsulfonamid (4-Brom-N-(pyridin-2- ylmethyl)naphthalin-1 -Sulfonamid) die Keimung von Pflanzensamen in der gleichen Weise wie Abscisinsäure beeinflusst (Park et al. Science 2009, 324, 1068-1071 ).Abscisic acid derivatives (Schading and Wei, WO2000 / 28055, Abrams and Gusta, US5201931, Abrams et al, WO97 / 23441, Churchill et al., 1998, Plant Growth Regul 25: 35-45). Furthermore, effects of growth regulators on the stress tolerance of crop plants have been described (Morrison and Andrews, 1992, J Plant Growth Regulation 11: 1 13-1 17, RD-259027). In this context, it is also known that a growth-regulating naphthylsulfonamide (4-bromo-N- (pyridin-2-ylmethyl) naphthalene-1-sulfonamide) influences the germination of plant seeds in the same manner as abscisic acid (Park et al., Science 2009, 324, 1068-1071).
Weiterhin zeigt eine Naphthylsulfamidocarbonsäure (N-[(4-Brom-1 -naphthyl)sulfonyl]- 5-methoxynorvalin) eine Wirkungsweise in biochemischen Rezeptortests, die mit 4- Brom-N-(pyridin-2-ylmethyl)naphthalin-1 -Sulfonamid vergleichbar ist (Melcher et al. Nature Structural & Molecular Biology 2010, 17, 1 102-1 108). Außerdem ist bekannt, dass ein weiteres Naphthylsulfonamid, N-(6-aminohexyl)-5-chlornaphthalin-1 - sulfonamid, den Calcium-Spiegel in Pflanzen beeinflusst, die einem Kälteschock ausgesetzt wurden (Cholewa et al. Can. J. Botany 1997, 75, 375-382). Auch bei Anwendung von Fungiziden, insbesondere aus der Gruppe der Strobilurine oder der Succinat Dehydrogenase Inhibitoren werden ähnliche Effekte beobachtet, die häufig auch mit einer Ertragssteigerung einhergehen (Draber et al., DE3534948, Bartlett et al., 2002, Pest Manag Sei 60: 309). Es ist ebenfalls bekannt, dass das Herbizid Glyphosat in niedriger Dosierung das Wachstum einiger Pflanzenarten stimuliert (Cedergreen, Env. Pollution 2008, 156, 1099). Furthermore, a naphthylsulfamidocarboxylic acid (N - [(4-bromo-1-naphthyl) sulfonyl] -5-methoxynorvaline) exhibits a mode of action in biochemical receptor assays that react with 4-bromo-N- (pyridin-2-ylmethyl) naphthalene-1-sulfonamide is comparable (Melcher et al., Nature Structural & Molecular Biology 2010, 17, 1, 102-1 108). It is also known another naphthylsulfonamide, N- (6-aminohexyl) -5-chloronaphthalene-1-sulfonamide, affects calcium levels in plants that have been cold shocked (Cholewa et al., Can. J. Botany 1997, 75, 375- 382). Similar effects are observed even when using fungicides, in particular from the group of strobilurins or succinate dehydrogenase inhibitors, which are often accompanied by an increase in yield (Draber et al., DE3534948, Bartlett et al., 2002, Pest Management, 60: 309 ). It is also known that the low dose herbicide glyphosate stimulates the growth of some plant species (Cedergreen, Env. Pollution 2008, 156, 1099).
Bei osmotischem Stress ist eine Schutzwirkung durch Applikation von Osmolyten wie z.B. Glycinbetain oder deren biochemischen Vorstufen, z.B. Cholin-Derivate At osmotic stress, a protective effect is provided by the application of osmolytes, e.g. Glycine betaine or its biochemical precursors, e.g. Choline derivatives
beobachtet worden (Chen et al., 2000, Plant Cell Environ 23: 609-618, Bergmann et al., DE4103253). Auch die Wirkung von Antioxidantien wie z.B Naphthole und (Chen et al., 2000, Plant Cell Environ 23: 609-618, Bergmann et al., DE4103253). Also, the effect of antioxidants such as naphthols and
Xanthine zur Erhöhung der abiotischen Stresstoleranz in Pflanzen wurde bereits beschrieben (Bergmann et al., DD277832, Bergmann et al., DD277835). Die molekularen Ursachen der Anti-Stress-Wirkung dieser Substanzen sind jedoch weitgehend unbekannt. Xanthines for increasing the abiotic stress tolerance in plants has already been described (Bergmann et al., DD277832, Bergmann et al., DD277835). However, the molecular causes of the anti-stress effects of these substances are largely unknown.
Es ist weiter bekannt, dass die Toleranz von Pflanzen gegenüber abiotischem Stress durch eine Modifikation der Aktivität von endogenen Poly-ADP-ribose Polymerasen (PARP) oder Poly-(ADP-ribose) glycohydrolasen (PARG) erhöht werden kann (de Block et al., The Plant Journal, 2004, 41, 95; Levine et al., FEBS Lett. 1998, 440, 1 ; WO00/04173; WO2004/090140). It is further known that the tolerance of plants to abiotic stress can be increased by a modification of the activity of endogenous poly-ADP-ribose polymerases (PARP) or poly (ADP-ribose) glycohydrolases (PARG) (de Block et al. , The Plant Journal, 2004, 41, 95; Levine et al., FEBS Lett. 1998, 440, 1, WO00 / 04173, WO2004 / 090140).
Somit ist bekannt, dass Pflanzen über mehrere endogene Reaktionsmechanismen verfügen, die eine wirksame Abwehr gegenüber verschiedensten Schadorganismen und/oder natürlichem abiotischem Stress bewirken können. Da sich die ökologischen und ökonomischen Anforderungen an moderne Pflanzenbehandlungsmittel laufend erhöhen, beispielsweise was deren Toxizität, Selektivität, Aufwandmenge, Thus, it is known that plants have several endogenous reaction mechanisms that can effectively prevent various harmful organisms and / or natural abiotic stress. Since the ecological and economic requirements of modern plant treatment products are constantly increasing, for example as regards their toxicity, selectivity, application rate,
Rückstandsbildung und günstige Herstellbarkeit angeht, besteht die ständige Aufgabe, neue Pflanzenbehandlungsmittel zu entwickeln, die zumindest in Teilbereichen With regard to the formation of residues and favorable producibility, there is the constant task of developing new plant treatment products, at least in some areas
Vorteile gegenüber den bekannten aufweisen. Daher bestand die Aufgabe der vorliegenden Erfindung darin, Verbindungen bereitzustellen, die die Toleranz gegenüber abiotischem Stress in Pflanzen weiter erhöhen, eine Stärkung des Pflanzenwachstums bewirken und/oder zur Erhöhung des Pflanzenertrags beitragen. In diesem Zusammenhang wird unter Toleranz gegenüber abiotischem Stress beispielsweise die Toleranz gegenüber Kälte-, Hitze-, Have advantages over the known. Therefore, the object of the present invention was to provide compounds which further increase the tolerance to abiotic stress in plants, cause a strengthening of plant growth and / or contribute to the increase of the plant yield. In this context, tolerance to abiotic stress, for example, tolerance to cold, heat,
Trockenstress (Stress verursacht durch Trockenheit und/oder Wassermangel), Salzen und Überflutung verstanden. Überraschenderweise wurde nun gefunden, daß substituierte  Drought stress (stress caused by drought and / or lack of water), salting and flooding understood. Surprisingly, it has now been found that substituted
Heteroarylcarbonsäurehydrazide zur Steigerung der Stresstoleranz in Pflanzen gegenüber abiotischem Stress, sowie zur Steigerung des Pflanzenwachstums und/oder zur Erhöhung des Pflanzenertrags verwendet werden können. Gegenstand der vorliegenden Erfindung sind demnach substituierte  Heteroarylcarbonsäurehydrazide can be used to increase the stress tolerance in plants to abiotic stress, as well as to increase plant growth and / or increase the plant yield. The subject of the present invention are therefore substituted
Heteroarylcarbonsäurehydrazide der allgemeinen Formel (I) oder deren Salze,  Heteroarylcarboxylic acid hydrazides of the general formula (I) or salts thereof,
R1, R2 und R7 unabhängig voneinander für Wasserstoff, Halogen, Cyano, Nitro, R 1 , R 2 and R 7 independently of one another represent hydrogen, halogen, cyano, nitro,
NR21R22, OR23, S(O)nR24, Thiocyanato, Isothiocyanato, (Ci-C8)-Alkyl, (C2-C8)- Alkenyl, (C2-C8)-Alkinyl, (Ci-Cio)-Haloalkyl, (C2-C8)-Haloalkenyl, (C2-C8)- Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-Cio)-Halocycloalkyl, (C4-Cio)-Cycloalkenyl,NR 21 R 22, OR 23, S (O) n R 24, thiocyanato, isothiocyanato, (Ci-C 8) -alkyl, (C 2 -C 8) - alkenyl, (C 2 -C 8) -alkynyl, ( Ci-Cio) -haloalkyl, (C 2 -C 8 ) -haloalkenyl, (C 2 -C 8 ) -haloalkynyl, (C 3 -Cio) -cycloalkyl, (C 3 -Cio) -halocycloalkyl, (C 4 -Cio ) cycloalkenyl,
(C4-Cio)-Halocycloalkenyl, Pentafluorthio, (Ci-C8)-Alkoxy-(Ci-C8)-haloalkyl, (Ci-C8)-Haloalkoxy-(Ci-C8)-haloalkyl, (Ci-C8)-Haloalkoxy-(Ci-C8)-alkyl, Aryl, Aryl-(Ci-C8)-alkyl, Heteroaryl, Heteroaryl-(Ci-C8)-alkyl, (C3-C8)-Cycloalkyl- (Ci-C8)-alkyl, (C4-Cio)-Cycloalkenyl-(Ci-C8)-alkyl, Heterocyclyl, Heterocyclyl- (Ci-Cs)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, (Ci -C8)-Al kylth io-(Ci -C8)-al kyl , (Ci-C8)-Haloalkylthio-(Ci-C8)-alkyl, (Ci-C8)-Alkylcarbonyl-(Ci-C8)-alkyl, COOR23, CONR21R22, COR23 , -C=NOR23, R21 R22N-(Ci-C8)-alkyl, R23OOC-(Ci-C8)-alkyl, Aryl-(Ci-C8)-alkinyl, Heteroaryl-(Ci-C8)-alkinyl, Heterocyclyl-(Ci-C8)-alkinyl, Tris- [(Ci-C8)-alkyl]silyl-(C2-C8)-alkinyl, Bis-[(Ci-C8)-alkyl](aryl)silyl-(C2-C8)-alkinyl, Bis-aryl[(Ci-C8)-alkyl]silyl-(C2-C8)-alkinyl, (C3-C8)-Cycloalkyl-(C2-C8)-alkinyl, Aryl-(C 4 -C 10) -halocycloalkenyl, pentafluorothio, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -haloalkoxy- (C 1 -C 8 ) -haloalkyl, C 8) haloalkoxy (Ci-C 8) alkyl, aryl, aryl (Ci-C 8) alkyl, heteroaryl, heteroaryl (Ci-C 8) alkyl, (C 3 -C 8) cycloalkyl (C 1 -C 8 ) -alkyl, (C 4 -C 10) -cycloalkenyl- (C 1 -C 8 ) -alkyl, heterocyclyl, heterocyclyl- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylthio (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkylthio (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylcarbonyl- (C 1 -C 8 ) -alkyl, COOR 23 , CONR 21 R 22 , COR 23 , -C = NOR 23, R 21 R 22 N- (Ci-C 8) alkyl, R 23 OOC- (Ci-C 8) alkyl, aryl (Ci-C 8) alkynyl, heteroaryl (Ci-C 8) alkynyl, heterocyclyl (Ci-C8) -alkynyl, tris [(Ci-C 8) alkyl] silyl (C 2 -C 8) -alkynyl, - bis [(Ci-C 8) alkyl] (aryl) silyl (C 2 -C 8) -alkynyl, bis-aryl [(Ci-C 8) alkyl] silyl (C 2 -C 8) -alkynyl, (C 3 -C 8) cycloalkyl (C 2 -C 8 ) -alkynyl, aryl-
(C2-C8)-al kenyl , Heteroaryl-(C2-C8)-al kenyl , Heterocyclyl-(C2-C8)-al kenyl , (C3-C8)-Cycloal kyl-(C2-C8)-al kenyl , (Ci -C8)-Al koxy-(Ci -C8)-al koxy-(Ci -C8)-al kyl , (Ci-C8)-Alkylaminosulfonylannino, (C3-C8)-Cycloalkylaminosulfonylannino, Diazo, Aryldiazo, Tris-[(Ci-C8)-alkyl]silyl, Bis-[(Ci-C8)-alkyl](aryl)silyl, Bis-aryl[(Ci-C8)- alkyl]silyl stehen, (C2-C8) -alkenyl, heteroaryl- (C2-C8) -alkenyl, heterocyclyl- (C2-C8) -alkenyl, (C 3 -C 8) -Cycloal alkyl- (C 2 -C 8) -alkenyl, (Ci-C8) -alkyl alkoxy- (Ci-C8) -al alkoxy- (Ci-C8) -alkyl, (Ci-C 8) -Alkylaminosulfonylannino, (C3-C 8 ) -Cycloalkylaminosulfonylannino, diazo, aryldiazo, tris - [(C 1 -C 8 ) -alkyl] silyl, bis - [(C 1 -C 8 ) -alkyl] (aryl) silyl, bis-aryl [(C 1 -C 8 ) - alkyl] silyl,
X1, X2 und X3 gleich oder verschieden sind und unabhängig voneinander für O X 1 , X 2 and X 3 are the same or different and are each independently O.
(Sauerstoff), S (Schwefel), N (Stickstoff), die Gruppierung C-R2 oder die (Oxygen), S (sulfur), N (nitrogen), the group CR 2 or the
Gruppierung N-R20 stehen, wobei jedoch in keinem Fall ein O- und S-Atom benachbart sind und wobei in keinem Fall jeweils mehr als ein O- oder S-Atom im gebildeten 5-gliedrigen Ring enthalten ist, und wobei R2 in der Gruppierung C-R2 und R20 in der Gruppierung N-R20 jeweils gleiche oder verschiedene Bedeutungen gemäß der oben- oder nachstehenden Definitionen haben, W für O (Sauerstoff) oder S (Schwefel) steht, Grouping NR 20 are, but in no case adjacent to an O and S atom and in each case in each case more than one O or S atom in the formed 5-membered ring is contained, and wherein R 2 in the grouping CR 2 and R 20 in the moiety NR 20 each have the same or different meanings according to the above or below definitions, W is O (oxygen) or S (sulfur),
A1, A2, A3, A4 und A5 gleich oder verschieden sind und unabhängig voneinander für N (Stickstoff) oder die Gruppierung C-R7 stehen, wobei jedoch in keinem Fall mehr als zwei N-Atome benachbart sind, und wobei R7 in der Gruppierung C-R7 jeweils gleiche oder verschiedene Bedeutungen gemäß der oben stehendenA 1 , A 2 , A 3 , A 4 and A 5 are the same or different and are independently N (nitrogen) or the group CR 7 , but in no case more than two N atoms are adjacent, and wherein R 7 in the group CR 7 each have the same or different meanings according to the above
Definition hat, Definition has,
R3 für (Ci-Cs)-Alkyl, Cyano-(Ci-C8)-Alkyl, (C2-C8)-Al kenyl, (C2-C8)-Alkinyl, (C1-C10)- Haloalkyl, (C2-C8)-Haloalkenyl, (C2-C8)-Haloalkinyl, (C3-Cio)-Cycloalkyl, R 3 is (Ci-Cs) alkyl, cyano (Ci-C 8) -alkyl, (C 2 -C 8) -alkenyl, (C 2 -C 8) -alkynyl, (C1-C10) - haloalkyl , (C 2 -C 8 ) -haloalkenyl, (C 2 -C 8 ) -haloalkynyl, (C 3 -C 10) -cycloalkyl,
(C3-Cio)-Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, , Aryl,(C 3 -C 10) -halocycloalkyl, (C 4 -C 10) -cycloalkenyl, (C 4 -C 10) -halocycloalkenyl,, aryl,
Aryl-(Ci-C8)-alkyl, Heteroaryl, Heteroaryl-(Ci-C8)-alkyl, (C3-C8)-Cycloalkyl- (Ci-Cs)-alkyl, Heterocyclyl, Heterocyclyl-(Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)- alkyl, (C1 -C8)-Al kylth io-(Ci -C8)-al kyl , (Ci-C8)-Haloalkoxy-(Ci-C8)-alkyl, (Ci-C8)- Haloalkylthio-(Ci-C8)-alkyl, R21R22N-(Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)- alkoxy-(Ci-C8)-alkyl steht, Aryl (Ci-C 8) alkyl, heteroaryl, heteroaryl (Ci-C 8) alkyl, (C 3 -C 8) -cycloalkyl- (Ci-Cs) alkyl, heterocyclyl, heterocyclyl (Ci-C 8) alkyl, (Ci-C 8) alkoxy (Ci-C 8) - alkyl, (C1-C8) -alkyl kylth io- (Ci-C8) -alkyl, (Ci-C 8) Haloalkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) - Haloalkylthio- (Ci-C 8) alkyl, R 21 R 22 N- (Ci-C8) alkyl, (Ci-C 8) alkoxy (Ci-C 8) - alkoxy- (Ci-C 8) alkyl,
R4 für Wasserstoff, (Ci-Cs)-Alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (C1-C10)- Haloalkyl, (C2-C8)-Haloalkenyl, (C2-C8)-Haloalkinyl, (C3-Cio)-Cycloalkyl, R 4 is hydrogen, (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, (C 1 -C 10) -haloalkyl, (C 2 -C 8 ) -haloalkenyl , (C 2 -C 8 ) -haloalkynyl, (C 3 -Cio) -cycloalkyl,
(C3-Cio)-Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, Aryl, Aryl-(Ci-C8)-alkyl, Heteroaryl, Heteroaryl-(Ci-C8)-alkyl, (C3-C8)-Cycloalkyl- (Ci-Cs)-alkyl, Heterocyclyl, Heterocyclyl-(Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)- alkyl, (C1 -C8)-Al kylth io-(Ci -C8)-al kyl , (Ci-C8)-Haloalkoxy-(Ci-C8)-alkyl, (Ci-C8)- Haloalkylthio-(Ci-C8)-alkyl, (Ci-C8)-Alkylamino-(Ci-C8)-alkyl, Bis-[(Ci-C8)- alkyl]amino-(Ci-C8)-alkyl, (C3-C8)-Cycloalkylamino-(Ci-C8)-alkyl, (Ci-Cs)-Alkoxy- (Ci-C8)-alkoxy-(Ci-C8)-alkyl, COR23, (Ci-Cs)-Alkoxycarbonyl, (C2-C8)- Al kenyloxycarbonyl , (C2-C8)-Al kinyloxycarbonyl , Aryl-(Ci -C8)-al koxycarbonyl , Heteroaryl-(Ci-C8)-alkoxycarbonyl, (C3-C8)-Cycloalkyl-(Ci-C8)-alkoxycarbonyl, CONR21R22, SO2R24, Hydroxycarbonyl-(Ci-C8)-alkyl, (Ci-Cs)-Alkoxycarbonyl- (C1 -C8)-al kyl , (C2-C8)-Al kenyloxycarbonyl-(Ci -C8)-al kyl , (C2-C8)- Alkinyloxycarbonyl-(Ci-C8)-alkyl, Aryl-(Ci-C8)-alkoxycarbonyl-(Ci-C8)-alkyl, Heteroaryl-(Ci-C8)-alkoxycarbonyl-(Ci-C8)-alkyl, Heterocyclyl-(Ci-C8)- alkoxycarbonyl-(Ci-C8)-alkyl, (Ci-C8)-Alkylcarbonyl-(Ci-C8)-alkyl, (Ci-C8)- Alkylsulfonyl-(Ci-C8)-alkyl, (Ci-C8)-Alkylsulfinyl-(Ci-C8)-alkyl steht, (C 3 -C 10) -halocycloalkyl, (C 4 -C 10) -cycloalkenyl, (C 4 -C 10) -halocycloalkenyl, aryl, aryl- (C 1 -C 8 ) -alkyl, heteroaryl, heteroaryl- (C 1 -C 8 ) - alkyl, (C 3 -C 8) -cycloalkyl- (Ci-Cs) alkyl, heterocyclyl, heterocyclyl (Ci-C8) alkyl, (Ci-C 8) alkoxy (Ci-C 8) - alkyl , (C1-C8) -alkyl kylth io- (Ci-C8) -alkyl, (Ci-C8) haloalkoxy (Ci-C 8) alkyl, (Ci-C 8) - Haloalkylthio- ( Ci-C 8) alkyl, (Ci-C 8) alkylamino (Ci-C8) alkyl, - bis [(Ci-C 8) - alkyl] amino- (Ci-C 8) alkyl, ( C3-C8) cycloalkylamino (Ci-C 8) alkyl, (Ci-Cs) alkoxy (Ci-C 8) alkoxy (Ci-C 8) alkyl, COR 23, (Ci-Cs ) alkoxycarbonyl, (C 2 -C 8) - Al alkenyloxycarbonyl, (C 2 -C 8) -alkyl kinyloxycarbonyl, aryl (Ci-C8) -al koxycarbonyl, heteroaryl (Ci-C8) alkoxycarbonyl, ( C3-C8) -cycloalkyl- (Ci-C8) -alkoxycarbonyl, CONR 21 R 22, SO 2 R 24, hydroxycarbonyl (Ci-C 8) alkyl, (Ci-Cs) -alkoxycarbonyl (C1 -C 8) -alkyl, (C 2 -C 8) -alkyl kenyloxycarbonyl- (Ci-C8) -alkyl, (C 2 -C 8) - alkynyloxycarbonyl (Ci-C 8) alkyl, aryl (C -C 8 ) -alkoxycarbonyl- (C 1 -C 8 ) -alkyl, heteroaryl- (C 1 -C 8 ) -alkoxycarbonyl- (C 1 -C 8 ) -alkyl, heterocyclyl- (C 1 -C 8 ) -alkoxycarbonyl- (C 1 -C 8 ) alkyl, (Ci-C8) alkylcarbonyl (Ci-C8) alkyl, (Ci-C 8) - alkylsulfonyl (Ci-C 8) alkyl, (Ci-C8) alkylsulfinyl ( Ci-C 8 ) -alkyl,
R5 und R6 unabhängig voneinander für Wasserstoff, (Ci-Cs)-Alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (Ci-Cio)-Haloalkyl, (C2-C8)-Haloalkenyl, (C2-C8)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-Cio)-Halocycloalkyl, (C-Cio)-Cycloalkenyl, (C-Cio)- Halocycloalkenyl, Aryl, Aryl-(Ci-C8)-alkyl, Heteroaryl, Heteroaryl-(Ci-C8)-alkyl, (C3-C8)-Cycloal kyl-(Ci -C8)-al kyl , Heterocyclyl , Heterocyclyl-(Ci -C8)-al kyl , R 5 and R 6 independently of one another represent hydrogen, (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, (C 1 -C 10) -haloalkyl, (C 2 -) C 8 ) -haloalkenyl, (C 2 -C 8 ) -haloalkynyl, (C 3 -C 10) -cycloalkyl, (C 3 -C 10) -halocycloalkyl, (C 1 -C 10) -cycloalkenyl, (C 1 -C 8 ) -halocycloalkenyl, aryl, aryl (Ci-C 8) alkyl, heteroaryl, heteroaryl (Ci-C 8) alkyl, (C3-C8) -Cycloal alkyl- (Ci-C8) -alkyl, heterocyclyl, heterocyclyl (C 1 -C 8 ) -alcyl,
(Ci-C8)-Alkoxy-(Ci-C8)-alkyl, (Ci-Cs)-Al kylth io-(Ci-C8)-al kyl, (Ci-Cs)-Haloalkoxy- (Ci-Cs)-alkyl, (Ci-C8)-Haloalkylthio-(Ci-C8)-alkyl, COOR23, CONR21R22, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylthio (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkoxy- (C 1 -C 8 ) -alkyl ) -alkyl, (C 1 -C 8 ) -haloalkylthio (C 1 -C 8 ) -alkyl, COOR 23 , CONR 21 R 22 ,
Hydroxycarbonyl-(Ci-C8)-alkyl, (Ci-C8)-Alkoxycarbonyl-(Ci-C8)-alkyl, (C2-C8)- Al kenyloxycarbonyl-(Ci -C8)-al kyl , (C2-C8)-Al kinyloxycarbonyl-(Ci -C8)-al kyl , Aryl- (Ci-C8)-alkoxycarbonyl-(Ci-C8)-alkyl, Heteroaryl-(Ci-C8)-alkoxycarbonyl-(Ci-C8)- al kyl , Heterocyclyl-(Ci -C8)-al koxycarbonyl-(Ci-C8)-al kyl stehen , R3 und R4 mit dem Stickstoffatom, an das sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3-7- gliedrigen Ring bilden, Hydroxycarbonyl- (Ci-C 8) alkyl, (Ci-C8) alkoxycarbonyl (Ci-C 8) alkyl, (C 2 -C 8) - Al kenyloxycarbonyl- (Ci-C8) -alkyl, (C 2 -C 8) -alkyl kinyloxycarbonyl- (Ci-C8) -alkyl, aryl (Ci-C8) alkoxycarbonyl (Ci-C 8) alkyl, heteroaryl (Ci-C8) - alkoxycarbonyl (Ci-C 8) - al kyl, heterocyclyl (Ci-C8) -al koxycarbonyl- (Ci-C 8) -alkyl stand, R 3 and R 4 with the nitrogen atom to which they are attached form a completely saturated, partially saturated or completely unsaturated, optionally interrupted by heteroatoms and optionally further substituted 3-7-membered ring,
R1 und X1, wenn X1 für eine Gruppe C-R2 steht, mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig R 1 and X 1 , when X 1 is a group CR 2 , with the atoms to which they are attached, a fully saturated, partially saturated or completely
ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden,  form unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring,
X1 und X2, wenn beide für eine Gruppe C-R2 stehen, mit den Atomen, an die sie X 1 and X 2 , when both represent a group CR 2 , with the atoms to which they belong
gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden,  form a fully saturated, partially saturated or fully unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring,
A1 und A2, wenn beide für eine Gruppe C-R7 stehen, mit den Atomen, an die sie A 1 and A 2 , when both represent a group CR 7 , with the atoms to which they belong
gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden,  form a fully saturated, partially saturated or fully unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring,
A2 und A3, wenn beide für eine Gruppe C-R7 stehen, mit den Atomen, an die sie A 2 and A 3 , when both represent a group CR 7 , with the atoms to which they belong
gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden und  form a fully saturated, partially saturated or fully unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5-7-membered ring and form
A3 und A4, wenn beide für eine Gruppe C-R7 stehen, mit den Atomen, an die sie A 3 and A 4 , when both represent a group CR 7 , with the atoms to which they belong
gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden,  form a fully saturated, partially saturated or fully unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring,
Y für eine Bindung oder für die Gruppierungen Y-1 bis Y-7 Y for a bond or for the groupings Y-1 to Y-7
steht, wobei R8, R9, R10, R1 1, R12, R13, R14, R15, R16, R17, R18 und R19 jeweils die , wherein R 8, R 9, R 10, R 1 1, R 12, R 13, R 14, R 15, R 16, R 17, R 18 and R 19 in each case the
Bedeutung gemäß der nachstehenden Definition haben und wobei der Pfeil für eine Bindung zum 6-gliedrigen Ring mit den Gruppierungen A1, A2, A3, A4 und A5 steht, Have meaning as defined below and wherein the arrow represents a bond to the 6-membered ring with the groupings A 1 , A 2 , A 3 , A 4 and A 5 ,
R8, R9, R10, R1 1, R12, R13, R14, R15, R16, R17, R18 und R19 unabhängig voneinander für Wasserstoff, Halogen, (Ci-C8)-Alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (C1-C10)- Haloalkyl, (C2-C8)-Haloalkenyl, (C2-C8)-Haloalkinyl, (C3-Cio)-Cycloalkyl, Aryl, Aryl-(Ci-C8)-alkyl, Heteroaryl, Heteroaryl-(Ci-C8)-alkyl, (C3-C8)-Cycloalkyl- (Ci-Cs)-alkyl, Heterocyclyl, Heterocyclyl-(Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)- alkyl, (C1 -C8)-Al kylth io-(Ci -C8)-al kyl , (Ci-C8)-Haloalkoxy-(Ci-C8)-alkyl, (Ci-C8)- Haloalkylthio-(Ci-C8)-alkyl, COOR23 stehen, R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 independently of one another represent hydrogen, halogen, (C 1 -C 8 ) alkyl, (C 2 -C 8) alkenyl, (C 2 -C 8) -alkynyl, (C1-C10) - haloalkyl, (C 2 -C 8) -haloalkenyl, (C 2 -C 8) haloalkynyl, (C 3 -Cio) cycloalkyl, aryl, aryl (Ci-C 8) alkyl, heteroaryl, heteroaryl (Ci-C 8) alkyl, (C 3 -C 8) -cycloalkyl- (Ci-Cs) alkyl, heterocyclyl, heterocyclyl (Ci-C8) alkyl, (Ci-C 8) alkoxy (Ci-C 8) - alkyl, (C1-C8) -alkyl kylth io- (Ci-C8 ) -alkyl, (C 1 -C 8 ) -haloalkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkylthio (C 1 -C 8 ) -alkyl, COOR 23 ,
R5 und R6 mit dem Atom, an das sie gebunden sind, einen vollständig gesättigten, oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden, R 5 and R 6 with the atom to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring,
R20 für Wasserstoff, (Ci-Cs)-Alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (C1-C10)- Haloalkyl, (C2-C8)-Haloalkenyl, (C2-C8)-Haloalkinyl, (C3-Cio)-Cycloalkyl, R 20 is hydrogen, (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, (C 1 -C 10) -haloalkyl, (C 2 -C 8 ) -haloalkenyl , (C 2 -C 8 ) -haloalkynyl, (C 3 -Cio) -cycloalkyl,
(C4-Cio)-Cycloalkenyl, (Ci-Cs)-Alkoxy, Aryl, Heteroaryl, Heterocyclyl, (Ci-C8)- Al kylcarbonyl , Aryl-(Ci -C8)-Al kylcarbonyl , (C3-C8)-Cycloal kylcarbonyl , (C 4 -Cio) cycloalkenyl, (Ci-Cs) alkoxy, aryl, heteroaryl, heterocyclyl, (Ci-C 8) - Al kylcarbonyl, aryl (Ci-C8) -alkyl kylcarbonyl, (C3-C 8 ) -Cycloalkylcarbonyl,
Arylcarbonyl, Heteroarylcarbonyl, (Ci-Cs)-Alkoxycarbonyl, (C2-C8)- Alkenyloxycarbonyl, Aryl-(Ci-C8)-alkoxycarbonyl, Heteroaryl-(Ci-Cs)- alkoxycarbonyl, (C3-C8)-Cycloalkyl-(Ci-C8)-alkoxycarbonyl, (Ci-Cs)-Alkylsulfonyl, (Ci-C8)-Haloalkylsulfonyl, Arylsulfonyl, Heteroarylsulfonyl, (C3-C8)- Cycloalkylsulfonyl, (Ci-CsJ-Alkylsulfinyl, Arylsulfinyl, Heteroarylsulfinyl, (C3-C8)- Cycloalkylsulfinyl steht, n für 0, 1 oder 2 steht Arylcarbonyl, heteroarylcarbonyl, (Ci-Cs) -alkoxycarbonyl, (C 2 -C 8) - alkenyloxycarbonyl, aryl (Ci-C8) -alkoxycarbonyl, heteroaryl (Ci-Cs) - alkoxycarbonyl, (C3-C8) - Cycloalkyl- (C 1 -C 8 ) -alkoxycarbonyl, (C 1 -C 8 ) -alkylsulfonyl, (C 1 -C 8 ) -haloalkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, (C 3 -C 8 ) - Cycloalkylsulfonyl, (Ci-CsJ-alkylsulfinyl, arylsulfinyl, heteroarylsulfinyl, (C 3 -C 8 ) - cycloalkylsulfinyl, n is 0, 1 or 2
R21 und R22 gleich oder verschieden sind und unabhängig voneinander für R 21 and R 22 are the same or different and independently of each other
Wasserstoff, (Ci-C8)-Alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (Ci-C8)-Cyanoalkyl, (Ci-Cio)-Haloalkyl, (C2-C8)-Haloalkenyl, (C2-C8)-Haloalkinyl, (C3-Cio)-Cycloalkyl (C3-Cio)-Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, Hydrogen, (Ci-C 8) alkyl, (C 2 -C 8) alkenyl, (C 2 -C 8) -alkynyl, (Ci-C 8) cyanoalkyl, (Ci-Cio) -haloalkyl, (C 2 -C 8 ) -haloalkenyl, (C 2 -C 8 ) -haloalkynyl, (C 3 -C 10) -cycloalkyl (C 3 -C 10) -halocycloalkyl, (C 4 -C 10) -cycloalkenyl, (C 4 -C 10) - Halocycloalkenyl,
(Ci-C8)-Alkoxy-(Ci-C8)-alkyl, (Ci-C8)-Haloalkoxy-(Ci-C8)-alkyl, (Ci-Cs)-Alkylthio- (Ci-Cs)-alkyl, (Ci-C8)-Haloalkylthio-(Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)- haloalkyl, Aryl, Aryl-(Ci-C8)-alkyl, Heteroaryl, Heteroaryl-(Ci-C8)-alkyl, (C3-C8)- Cycloalkyl-(Ci-C8)-alkyl, (C4-Cio)-Cycloalkenyl-(Ci-C8)-alkyl, COR23, SO2R24, (Ci-C8)-Alkyl-HNO2S-, (C3-C8)-Cycloalkyl-HNO2S-, Heterocyclyl, (Ci-C8)- Alkoxycarbonyl-(Ci-C8)-alkyl, (Ci-Cs)-Alkoxycarbonyl, Aryl-(Ci-Cs)- Alkoxycarbonyl-(Ci-C8)-alkyl, Aryl-(Ci-C8)-Alkoxycarbonyl, Heteroaryl-(Ci-Cs)- Al koxycarbonyl , (C2-C8)-Al kenyloxycarbonyl , (C2-C8)-Al ki nyloxycarbonyl , Heterocyclyl-(Ci-C8)-alkyl stehen R23 für Wasserstoff, (Ci-Cs)-Alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (Ci-C8)- Cyanoalkyl, (Ci-Cio)-Haloalkyl, (C2-C8)-Haloalkenyl, (C2-C8)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-Cio)-Halocycloalkyl, (C-Cio)-Cycloalkenyl, (C-Cio)- Halocycloalkenyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)-haloalkyl Aryl, Aryl-(Ci-C8)-alkyl, Heteroaryl, Heteroaryl-(Ci-C8)-alkyl, (C3-C8)-Cycloalkyl- (Ci-C8)-alkyl, (C-Cio)-Cycloalkenyl-(Ci-C8)-alkyl, (Ci-C8)-Alkoxycarbonyl- (C1 -C8)-al kyl , (C2-C8)-Al kenyloxycarbonyl-(Ci -C8)-al kyl , Aryl-(Ci -C8)- Al koxycarbonyl-(Ci -C8)-al kyl , Hydroxycarbonyl-(Ci -C8)-al kyl , Heterocyclyl , Heterocyclyl-(Ci-C8)-alkyl steht und (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylthio (C 1 -C 8 ) -alkyl - alkyl, (C 1 -C 8 ) -haloalkylthio (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -haloalkyl, aryl, aryl- (C 1 -C 8 ) -alkyl , heteroaryl, heteroaryl (Ci-C 8) alkyl, (C 3 -C 8) - cycloalkyl, (Ci-C 8) alkyl, (C 4 -Cio) cycloalkenyl (Ci-C 8) -alkyl , COR 23, SO 2 R 24, (Ci-C 8) -alkyl-HNO 2 S, (C 3 -C 8) cycloalkyl-HNO 2 S, heterocyclyl, (Ci-C8) - alkoxycarbonyl ( C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxycarbonyl, aryl- (C 1 -C 5 ) -alkoxycarbonyl- (C 1 -C 8 ) -alkyl, aryl- (C 1 -C 8 ) -alkoxycarbonyl, heteroaryl- (C 1 -C 4) -alkoxycarbonyl, -Cs) - Al koxycarbonyl, (C 2 -C 8) -alkyl alkenyloxycarbonyl, (C 2 -C 8) -alkyl ki nyloxycarbonyl, heterocyclyl (Ci-C 8) alkyl, R 23 is hydrogen, (Ci-Cs ) alkyl, (C 2 -C 8) alkenyl, (C 2 -C 8) -alkynyl, (Ci-C 8) - cyanoalkyl, (Ci-Cio) -haloalkyl, (C 2 -C 8) -haloalkenyl , (C 2 -C 8) haloalkynyl, (C 3 -Cio) cycloalkyl, (C 3 -Cio) halocycloalkyl, (C-Cio) cycloalkenyl, (C-Cio) - Halocycloalkenyl, (Ci-C 8 ) -A lkoxy- (Ci-C 8) alkyl, (Ci-C 8) alkoxy (Ci-C8) -haloalkyl aryl, aryl (Ci-C 8) alkyl, heteroaryl, heteroaryl (Ci-C 8 ) alkyl, (C 3 -C 8) cycloalkyl (Ci-C8) alkyl, (C-Cio) cycloalkenyl (Ci-C 8) alkyl, (Ci-C8) alkoxycarbonyl ( C1-C8) -alkyl, (C 2 -C 8) -alkyl kenyloxycarbonyl- (Ci-C8) -alkyl, aryl (Ci-C8) - Al koxycarbonyl- (Ci-C8) -al kyl, hydroxycarbonyl (C 1 -C 8 ) -alkyl, heterocyclyl, heterocyclyl- (C 1 -C 8 ) -alkyl and
R24 für Wasserstoff, (Ci-C8)-Alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (Ci-C8)- Cyanoalkyl, (Ci-Cio)-Haloalkyl, (C2-C8)-Haloalkenyl, (C2-C8)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-Cio)-Halocycloalkyl, (C-Cio)-Cycloalkenyl, (C-Cio)- Halocycloalkenyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)-haloalkyl Aryl, Aryl-(Ci-C8)-alkyl, Heteroaryl, Heteroaryl-(Ci-C8)-alkyl, Heterocyclyl- (Ci-C8)-alkyl, (C3-C8)-Cycloalkyl-(Ci-C8)-alkyl, (C -Cio)-Cycloalkenyl-(Ci-C8)- alkyl, NR21R22 steht. R 24 is hydrogen, (Ci-C 8) alkyl, (C 2 -C 8) alkenyl, (C 2 -C 8) -alkynyl, (Ci-C 8) - cyanoalkyl, (Ci-Cio) -haloalkyl , (C 2 -C 8 ) -haloalkenyl, (C 2 -C 8 ) -haloalkynyl, (C 3 -C 10) -cycloalkyl, (C 3 -C 10) -halocycloalkyl, (C 1 -C 8 ) -cycloalkenyl, Cio) - halocycloalkenyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -haloalkyl aryl, aryl- (C 1 -C 8 ) alkyl, heteroaryl, heteroaryl- (C 1 -C 8 ) -alkyl, heterocyclyl (Ci-C 8) alkyl, (C3-C8) -cycloalkyl- (Ci-C8) alkyl, (C -Cio) cycloalkenyl (Ci-C 8) - alkyl, NR 21 R 22.
Die Verbindungen der allgemeinen Formel (I) können durch Anlagerung einer geeigneten anorganischen oder organischen Säure, wie beispielsweise Mineralsäuren, wie beispielsweise HCl, HBr, H2SO4, H8PO4 oder HNO3, oder organische Säuren, z. B. Carbonsäuren, wie Ameisensäure, Essigsäure, Propionsäure, Oxalsäure, Milchsäure oder Salicylsäure oder Sulfonsäuren, wie zum Beispiel p-Toluolsulfonsäure, an eine basische Gruppe, wie z.B. Amino, Alkylamino, Dialkylamino, Piperidino, Morpholino oder Pyridino, Salze bilden. Diese Salze enthalten dann die konjugierte Base der Säure als Anion. Geeignete Substituenten, die in deprotonierter Form, wie z.B. The compounds of general formula (I) may be prepared by addition of a suitable inorganic or organic acid such as, for example, mineral acids such as HCl, HBr, H 2 SO 4 , H 8 PO 4 or HNO 3 , or organic acids, e.g. For example, carboxylic acids such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or sulfonic acids such as p-toluenesulfonic acid to form a basic group such as amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino, salts. These salts then contain the conjugate base of the acid as an anion. Suitable substituents which are in deprotonated form, such as
Sulfonsäuren, bestimmte Sulfonsäureamide oder Carbonsäuren, vorliegen, können innere Salze mit ihrerseits protonierbaren Gruppen, wie Aminogruppen bilden. Sulfonic acids, certain sulfonic acid amides or carboxylic acids are present, internal salts can in turn form protonatable groups, such as amino groups.
Salzbildung kann auch durch Einwirkung einer Base auf Verbindungen der Salt formation can also be effected by the action of a base on compounds of the
allgemeinen Formel (I) erfolgen. Geeignete Basen sind beispielsweise organische Amine, wie Trialkylamine, Morpholin, Piperidin und Pyridin sowie Ammonium-, Alkalioder Erdalkalimetallhydroxide, -carbonate und -hydrogencarbonate, insbesondere Natrium- und Kaliumhydroxid, Natrium- und Kaliumcarbonat und Natrium- und general formula (I). Suitable bases are, for example, organic amines, such as trialkylamines, morpholine, piperidine and pyridine, and ammonium, alkali or alkaline earth metal hydroxides, carbonates and bicarbonates, in particular sodium and potassium hydroxide, sodium and potassium carbonate and sodium and
Kaliumhydrogencarbonat. Diese Salze sind Verbindungen, in denen der acide Potassium bicarbonate. These salts are compounds in which the acidic
Wasserstoff durch ein für die Landwirtschaft geeignetes Kation ersetzt wird, Hydrogen is replaced by a cation suitable for agriculture,
beispielsweise Metallsalze, insbesondere Alkalimetall-salze oder Erdalkalimetallsalze, insbesondere Natrium- und Kaliumsalze, oder auch Ammoniumsalze, Salze mit organischen Aminen oder quartäre Ammoniumsalze, zum Beispiel mit Kationen der Formel [NRaRbRcRd]+, worin Ra bis Rd jeweils unabhängig voneinander einen For example, metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or ammonium salts, salts with organic amines or quaternary ammonium salts, for example with cations of the formula [NR a R b R c R d ] + , wherein R a to Each R d is independently one
organischen Rest, insbesondere Alkyl, Aryl, Aralkyl oder Alkylaryl darstellen. Infrage kommen auch Alkylsulfonium- und Alkylsulfoxoniumsalze, wie (Ci-C4)- Trialkylsulfonium- und (Ci-C4)-Trialkylsulfoxoniumsalze. represent organic radical, in particular alkyl, aryl, aralkyl or alkylaryl. In question are also alkylsulfonium and Alkylsulfoxoniumsalze, such as (Ci-C4) - trialkylsulfonium and (Ci-C 4) -Trialkylsulfoxoniumsalze.
Die erfindungsgemäßen Heteroarylcarbonsäurehydrazide der Formel (I) können in Abhängigkeit von äußeren Bedingungen, wie pH-Wert, Lösungsmittel und Temperatur sowie X1, X2 und X3 in verschiedenen tautomeren Strukturen vorliegen, die alle von der allgemeinen Formel (I) umfasst sein sollen. Im Folgenden werden die erfindungsgemäß verwendeten Verbindungen der Formel (I) und ihre Salze "Verbindungen der allgemeinen Formel (I)" bezeichnet. The Heteroarylcarbonsäurehydrazide of the formula (I) may, depending on external conditions such as pH, solvent, and temperature, as well as X 1, X 2 are present, and X 3 in different tautomeric structures, all of which are intended to be embraced by the general formula (I) , The compounds of the formula (I) used according to the invention and their salts are referred to below as "compounds of the general formula (I)".
Bevorzugter Erfindungsgegenstand sind Verbindungen der allgemeinen Formel (I), worin Preferred subject of the invention are compounds of the general formula (I) wherein
R1, R2 und R7 unabhängig voneinander für Wasserstoff, Halogen, Cyano, Nitro, R 1 , R 2 and R 7 independently of one another represent hydrogen, halogen, cyano, nitro,
NR21R22, OR23, S(O)nR24, Thiocyanato, Isothiocyanato, (Ci-C7)-Alkyl, (C2-C7)- Alkenyl, (C2-C7)-Alkinyl, (Ci-C7)-Haloalkyl, (C2-C7)-Haloalkenyl, (C2-C7)- Haloalkinyl, (C3-C7)-Cycloalkyl, (C3-C7)-Halocycloalkyl, (C -C7)-Cycloalkenyl,NR 21 R 22, OR 23, S (O) n R 24, thiocyanato, isothiocyanato, (Ci-C7) alkyl, (C 2 -C 7) - alkenyl, (C 2 -C 7) alkynyl, ( C 1 -C 7 ) -haloalkyl, (C 2 -C 7 ) -haloalkenyl, (C 2 -C 7 ) -haloalkynyl, (C 3 -C 7 ) -cycloalkyl, (C 3 -C 7 ) -halocycloalkyl, (C -C 7 ) cycloalkenyl,
(C -C7)-Halocycloalkenyl, Pentafluorthio, (Ci-C7)-Alkoxy-(Ci-C7)-haloalkyl, (C -C7) -Halocycloalkenyl, pentafluorosulfanyl, (Ci-C7) alkoxy (Ci-C7) haloalkyl,
(Ci-C7)-Haloalkoxy-(Ci-C7)-haloalkyl, (Ci-C7)-Haloalkoxy-(Ci-C7)-alkyl, Aryl, Aryl-(Ci-C7)-alkyl, Heteroaryl, Heteroaryl-(Ci-C7)-alkyl, (C3-C7)-Cycloalkyl- (Ci-C7)-alkyl, (C4-C7)-Cycloalkenyl-(Ci-C7)-alkyl, Heterocyclyl, Heterocyclyl- (Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, (Ci-C7)-Alkylthio-(Ci-C7)-alkyl, (C 1 -C 7 ) -haloalkoxy- (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -haloalkoxy- (C 1 -C 7 ) -alkyl, aryl, aryl- (C 1 -C 7 ) -alkyl, heteroaryl , heteroaryl (Ci-C7) alkyl, (C 3 -C 7) cycloalkyl (Ci-C7) alkyl, (C 4 -C 7) cycloalkenyl (C 7) alkyl, Heterocyclyl, heterocyclyl- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkylthio (C 1 -C 7 ) -alkyl,
(Ci-C7)-Haloalkylthio-(Ci-C7)-alkyl, (Ci-C7)-Alkylcarbonyl-(Ci-C7)-alkyl, COOR23, CONR21R22, COR23 , -C=NOR23, R21 R22N-(Ci-C7)-alkyl, R23OOC-(Ci-C7)-alkyl, Aryl-(Ci-C7)-alkinyl, Heteroaryl-(Ci-C7)-alkinyl, Heterocyclyl-(Ci-C7)-alkinyl, Tris- [(Ci-C7)-alkyl]silyl-(C2-C7)-alkinyl, Bis-[(Ci-C7)-alkyl](aryl)silyl-(C2-C7)-alkinyl, Bis-aryl[(Ci-C7)-alkyl]silyl-(C2-C7)-alkinyl, (C3-C7)-Cycloalkyl-(C2-C7)-alkinyl, Aryl-(C 1 -C 7 ) -haloalkylthio (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkylcarbonyl- (C 1 -C 7 ) -alkyl, COOR 23 , CONR 21 R 22 , COR 23 , -C = NOR 23, R 21 R 22 N- (C 7) alkyl, R 23 OOC- (C 7) alkyl, aryl (Ci-C7) alkynyl, heteroaryl (Ci-C 7) alkynyl, heterocyclyl (Ci-C7) alkynyl, tris [(Ci-C 7) alkyl] silyl (C 2 -C 7) alkynyl, - bis [(Ci-C 7) alkyl] (aryl) silyl (C 2 -C 7) alkynyl, bis-aryl [(Ci-C 7) alkyl] (C 2 -C 7) silyl- -alkynyl, (C 3 -C 7) cycloalkyl (C 2 -C 7 ) -alkynyl, aryl-
(C2-C7)-al kenyl , Heteroaryl-(C2-C7)-al kenyl , Heterocyclyl-(C2-C7)-al kenyl , (C3-C7)-Cycloal kyl-(C2-C7)-al kenyl , (Ci -C7)-Al koxy-(Ci -C7)-al koxy-(Ci -C7)-al kyl , (Ci-C7)-Alkylaminosulfonylamino, (C3-C7)-Cycloalkylaminosulfonylamino, Diazo, Aryldiazo, Tris-[(Ci-C7)-alkyl]silyl, Bis-[(Ci-C7)-alkyl](aryl)silyl, Bis-aryl[(Ci-C7)- alkyl]silyl stehen, (C 2 -C 7 ) -alkenyl, heteroaryl- (C 2 -C 7 ) -alkenyl, heterocyclyl- (C 2 -C 7 ) -alkenyl, (C 3 -C 7 ) -cycloalkyl (C 2 -C 7) -alkenyl, (Ci-C7) -alkyl alkoxy- (Ci -C 7) -al alkoxy- (Ci-C7) -alkyl, (Ci-C 7) -Alkylaminosulfonylamino, (C 3 -C 7) -Cycloalkylaminosulfonylamino, diazo, Aryldiazo, tris - [(Ci-C 7) alkyl] silyl, bis - [(Ci-C 7) alkyl] (aryl) silyl, bis-aryl [(Ci- C 7 ) - alkyl] silyl,
X1, X2 und X3 gleich oder verschieden sind und unabhängig voneinander für O X 1 , X 2 and X 3 are the same or different and are each independently O.
(Sauerstoff), S (Schwefel), N (Stickstoff), die Gruppierung C-R2 oder die (Oxygen), S (sulfur), N (nitrogen), the group CR 2 or the
Gruppierung N-R20 stehen, wobei jedoch in keinem Fall ein O- und S-Atom benachbart sind und wobei in keinem Fall jeweils mehr als ein O- oder S-Atom im gebildeten 5-gliedrigen Ring enthalten ist, und wobei R2 in der Gruppierung C-R2 und R20 in der Gruppierung N-R20 jeweils gleiche oder verschiedene Bedeutungen gemäß der oben- oder nachstehenden Definitionen haben, W für O (Sauerstoff) oder S (Schwefel) steht, Grouping NR 20 are, but in no case adjacent to an O and S atom and in each case in each case more than one O or S atom in the formed 5-membered ring is contained, and wherein R 2 in the grouping CR 2 and R 20 in moiety NR 20 each have the same or different meanings according to the above or below definitions, W is O (oxygen) or S (sulfur),
A1, A2, A3, A4 und A5 gleich oder verschieden sind und unabhängig voneinander für N (Stickstoff) oder die Gruppierung C-R7 stehen, wobei jedoch in keinem Fall mehr als zwei N-Atome benachbart sind, und wobei R7 in der Gruppierung C-R7 jeweils gleiche oder verschiedene Bedeutungen gemäß der oben stehenden Definition hat, A 1 , A 2 , A 3 , A 4 and A 5 are the same or different and are independently N (nitrogen) or the group CR 7 , but in no case more than two N atoms are adjacent, and wherein R 7 in the group CR 7 has the same or different meanings as defined above,
R3 für (Ci-C7)-Alkyl, Cyano-(Ci-C7)-Alkyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (Ci-C7)- Haloalkyl, (C2-C7)-Haloalkenyl, (C2-C7)-Haloalkinyl, (C3-C7)-Cycloalkyl, (C3-C7)- Halocycloalkyl, (C4-C7)-Cycloalkenyl, (C4-C7)-Halocycloalkenyl, , Aryl, Aryl- (Ci-C7)-alkyl, Heteroaryl, Heteroaryl-(Ci-C7)-alkyl, (C3-C7)-Cycloalkyl-(Ci-C7)- alkyl, Heterocyclyl, Heterocyclyl-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, (C 1 -C7)-Al ky Ith io-(C 1 -C7)-al ky I , (Ci-C7)-Haloalkoxy-(Ci-C7)-alkyl, (Ci-C7)- Haloalkylthio-(Ci-C7)-alkyl, R21R22N-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)- alkoxy-(Ci-C7)-alkyl steht, R 3 is (C 7) alkyl, cyano (Ci-C7) alkyl, (C 2 -C 7) alkenyl, (C 2 -C 7) alkynyl, (Ci-C7) - Haloalkyl, (C 2 -C 7 ) -haloalkenyl, (C 2 -C 7 ) -haloalkynyl, (C 3 -C 7 ) -cycloalkyl, (C 3 -C 7 ) -halocycloalkyl, (C 4 -C 7 ) - cycloalkenyl, (C 4 -C 7) -Halocycloalkenyl, aryl, aryl (Ci-C7) alkyl, heteroaryl, heteroaryl (Ci-C7) alkyl, (C 3 -C 7) -cycloalkyl- ( Ci-C7) - alkyl, heterocyclyl, heterocyclyl (Ci-C7) alkyl, (Ci-C7) alkoxy (Ci-C7) alkyl, (C 1 -C 7) -alkyl ky Ith io- (C 1 -C 7) -al ky I, (Ci-C7) haloalkoxy (Ci-C7) alkyl, (Ci-C7) - Haloalkylthio- (Ci-C7) alkyl, R 21 R 22 N- (C 7) alkyl, (Ci-C7) alkoxy (Ci-C7) - alkoxy- (Ci-C7) alkyl,
R4 für Wasserstoff, (Ci-C7)-Alkyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (Ci-C7)-R 4 represents hydrogen, (Ci-C7) alkyl, (C 2 -C 7) alkenyl, (C 2 -C 7) alkynyl, (Ci-C7) -
Haloalkyl, (C2-C7)-Haloalkenyl, (C2-C7)-Haloalkinyl, (C3-C7)-Cycloalkyl, (C3-C7)- Halocycloalkyl, (C4-C7)-Cycloalkenyl, (C4-C7)-Halocycloalkenyl, Aryl, Aryl- (Ci-C7)-alkyl, Heteroaryl, Heteroaryl-(Ci-C7)-alkyl, (C3-C7)-Cycloalkyl-(Ci-C7)- alkyl, Heterocyclyl, Heterocyclyl-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, (C 1 -C7)-Al ky Ith io-(C 1 -C7)-al ky I , (Ci-C7)-Haloalkoxy-(Ci-C7)-alkyl, (Ci-C7)- Haloalkylthio-(Ci-C7)-alkyl, (Ci-C7)-Alkylamino-(Ci-C7)-alkyl, Bis-[(Ci-C7)- alkyl]amino-(Ci-C7)-alkyl, (C3-C7)-Cycloalkylamino-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy- (Ci-C7)-alkoxy-(Ci-C7)-alkyl, COR23, (Ci-C7)-Alkoxycarbonyl, (C2-C7)- Al kenyloxycarbonyl , (C2-C7)-Al kinyloxycarbonyl , Aryl-(Ci -C7)-al koxycarbonyl , Heteroaryl-(Ci-C7)-alkoxycarbonyl, (C3-C7)-Cycloalkyl-(Ci-C7)-alkoxycarbonyl, CONR21R22, SO2R24, Hydroxycarbonyl-(Ci-C7)-alkyl, (Ci-C7)-Alkoxycarbonyl- (Ci -C7)-al kyl , (C2-C7)-Al kenyloxycarbonyl-(Ci -C7)-al kyl , (C2-C7)- Alkinyloxycarbonyl-(Ci-C7)-alkyl, Aryl-(Ci-C7)-alkoxycarbonyl-(Ci-C7)-alkyl, Heteroaryl-(Ci-C7)-alkoxycarbonyl-(Ci-C7)-alkyl, Heterocyclyl-(Ci-C7)- alkoxycarbonyl-(Ci-C7)-alkyl, (Ci-C7)-Alkylcarbonyl-(Ci-C7)-alkyl, (Ci-C7)- Alkylsulfonyl-(Ci-C7)-alkyl, (Ci-C7)-Alkylsulfinyl-(Ci-C7)-alkyl steht, R5 und R6 unabhängig voneinander für Wasserstoff, (Ci-C7)-Alkyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (Ci-C7)-Haloalkyl, (C2-C7)-Haloalkenyl, (C2-C7)-Haloalkinyl, (C3-C7)-Cycloalkyl, (C3-C7)-Halocycloalkyl, (C -C7)-Cycloalkenyl, (C -C7)- Halocycloalkenyl, Aryl, Aryl-(Ci-C7)-alkyl, Heteroaryl, Heteroaryl-(Ci-C7)-alkyl, (C3-C7)-Cycloal kyl-(Ci -C7)-al kyl , Heterocyclyl , Heterocyclyl-(Ci -C7)-al kyl , (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, (C 1 -C7)-Al ky Ith io-(Ci -C7)-a I ky I , (Ci-C7)-Haloalkoxy- (Ci-C7)-alkyl, (Ci-C7)-Haloalkylthio-(Ci-C7)-alkyl, COOR23, CONR21 R22, Haloalkyl, (C 2 -C 7 ) -haloalkenyl, (C 2 -C 7 ) -haloalkynyl, (C 3 -C 7 ) -cycloalkyl, (C 3 -C 7 ) -halocycloalkyl, (C 4 -C 7 ) - cycloalkenyl, (C 4 -C 7) -Halocycloalkenyl, aryl, aryl (Ci-C7) alkyl, heteroaryl, heteroaryl (Ci-C7) alkyl, (C 3 -C 7) -cycloalkyl- (C -C 7 ) - alkyl, heterocyclyl, heterocyclyl (Ci-C 7 ) alkyl, (Ci-C 7 ) -Alkoxy- (Ci-C 7 ) -alkyl, (C 1 -C 7 ) -Al ky Ith io - (C 1 -C 7) -al ky I, (Ci-C7) haloalkoxy (Ci-C7) alkyl, (Ci-C7) - Haloalkylthio- (Ci-C7) alkyl, ( Ci-C7) alkylamino- (Ci-C7) alkyl, - bis [(Ci-C7) - alkyl] amino- (Ci-C7) alkyl, (C 3 -C 7) cycloalkylamino (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, COR 23 , (C 1 -C 7 ) -alkoxycarbonyl, (C 2 -C 7) - Al alkenyloxycarbonyl, (C 2 -C 7) -alkyl kinyloxycarbonyl, aryl (Ci -C 7) -al koxycarbonyl, heteroaryl (Ci-C7) -alkoxycarbonyl, (C 3 -C 7) cycloalkyl (Ci-C7) -alkoxycarbonyl, CONR 21 R 22, SO 2 R 24, hydroxycarbonyl (C 7) alkyl, (Ci-C 7) alkoxycarbonyl (Ci -C 7) -al kyl, (C 2 -C 7 ) -Al kenyloxycarbonyl- (Ci -C 7 ) -alcyl, (C 2 -C 7 ) - alkynyloxycarbonyl (Ci-C 7 ) alkyl, aryl- (Ci-C 7 ) -alkoxycarbonyl- (Ci -C 7) alkyl, heteroaryl (Ci-C7) alkoxycarbonyl (Ci-C7) alkyl, heterocyclyl (Ci-C7) - alkoxycarbonyl (Ci-C7) alkyl, (Ci- C 7) alkylcarbonyl (Ci-C7) alkyl, (Ci-C7) - alkylsulfonyl (Ci-C 7) alkyl, (Ci-C 7) alkylsulfinyl (Ci-C7) alkyl stands, R 5 and R 6 are each independently hydrogen, (Ci-C7) alkyl, (C2-C7) alkenyl, (C 2 -C 7) alkynyl, (Ci-C7) haloalkyl, (C 2 -C 7 ) -haloalkenyl, (C 2 -C 7 ) -haloalkynyl, (C 3 -C 7 ) -cycloalkyl, (C 3 -C 7 ) -halocycloalkyl, (C -C 7 ) -cycloalkenyl, (C -C 7 ) - Halocycloalkenyl, aryl, aryl (Ci-C7) alkyl, heteroaryl, heteroaryl (Ci-C7) alkyl, (C 3 -C 7) -Cycloal alkyl- (Ci-C7) -alkyl, heterocyclyl, heterocyclyl- (Ci-C7) -alkyl, (Ci-C7) alkoxy (Ci-C7) alkyl, (C 1 -C 7) -alkyl ky Ith io- (Ci-C7) - a I ky I, (C 1 -C 7 ) -haloalkoxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkylthio (C 1 -C 7 ) -alkyl, COOR 23 , CONR 21 R 22 ,
Hydroxycarbonyl-(Ci -C7)-al kyl , (Ci -C7)-Al koxycarbonyl-(Ci -C7)-al kyl , (C2-C7)- Al kenyloxycarbonyl-(Ci -C7)-al kyl , (C2-C7)-Al kinyloxycarbonyl-(Ci -C7)-al kyl , Aryl- (Ci-C7)-alkoxycarbonyl-(Ci-C7)-alkyl, Heteroaryl-(Ci-C7)-alkoxycarbonyl-(Ci-C7)- alkyl, Heterocyclyl-(Ci-C7)-alkoxycarbonyl-(Ci-C7)-alkyl stehen, Hydroxycarbonyl- (C 1 -C 7 ) -alkenyl, (C 1 -C 7 ) -alkoxycarbonyl- (C 1 -C 7 ) -alkyl, (C 2 -C 7 ) -alkhenyloxycarbonyl- (C 1 -C 7 ) -alkyl, (C 2 -C 7) -alkynyloxycarbonyl- (C 1 -C 7) -alkyl, aryl- (C 1 -C 7) -alkoxycarbonyl- (C 1 -C 7) -alkyl, heteroaryl- (C 1 -C 7) -alkoxycarbonyl- (C 1 -C 7 ) - alkyl, heterocyclyl- (C 1 -C 7) -alkoxycarbonyl- (C 1 -C 7) -alkyl,
R3 und R4 mit dem Stickstoffatom, an das sie gebunden sind, einen vollständig R 3 and R 4 with the nitrogen atom to which they are attached, a complete
gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3-7- gliedrigen Ring bilden,  form saturated, partially saturated or completely unsaturated, optionally interrupted by heteroatoms and optionally further substituted 3-7-membered ring,
R1 und X1 , wenn X1 für eine Gruppe C-R2 steht, mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig R 1 and X 1 , when X 1 is a group CR 2 , with the atoms to which they are attached, a fully saturated, partially saturated or completely
ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden,  form unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring,
X1 und X2, wenn beide für eine Gruppe C-R2 stehen, mit den Atomen, an die sie X 1 and X 2 , when both represent a group CR 2 , with the atoms to which they belong
gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden,  form a fully saturated, partially saturated or fully unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring,
A1 und A2, wenn beide für eine Gruppe C-R7 stehen, mit den Atomen, an die sie A 1 and A 2 , when both represent a group CR 7 , with the atoms to which they belong
gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden, A2 und A3, wenn beide für eine Gruppe C-R7 stehen, mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden und form a fully saturated, partially saturated or fully unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring, A 2 and A 3 , when both represent a group CR 7 , with the atoms to which they are attached form a fully saturated, partially saturated or fully unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring, and
A3 und A4, wenn beide für eine Gruppe C-R7 stehen, mit den Atomen, an die sie A 3 and A 4 , when both represent a group CR 7 , with the atoms to which they belong
gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden,  form a fully saturated, partially saturated or fully unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring,
Y für eine Bindung oder für die Gruppierungen Y-1 bis Y-7 Y for a bond or for the groupings Y-1 to Y-7
steht, wobei R8, R9, R10, R1 1, R12, R13, R14, R15, R16, R17, R18 und R19 jeweils die , wherein R 8, R 9, R 10, R 1 1, R 12, R 13, R 14, R 15, R 16, R 17, R 18 and R 19 in each case the
Bedeutung gemäß der nachstehenden Definition haben und wobei der Pfeil für eine Bindung zum 6-gliedrigen Ring mit den Gruppierungen A1, A2, A3, A4 und A5 steht, R8, R9, R10, R1 1, R12, R13, R14, R15, R16, R17, R18 und R19 unabhängig voneinander für Wasserstoff, Halogen, (Ci-C7)-Alkyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (Ci-C7)- Haloalkyl, (C2-C7)-Haloalkenyl, (C2-C7)-Haloalkinyl, (C3-C7)-Cycloalkyl, Aryl, Aryl-(Ci-C7)-alkyl, Heteroaryl, Heteroaryl-(Ci-C7)-alkyl, (C3-C7)-Cycloalkyl- (Ci-C7)-alkyl, Heterocyclyl, Heterocyclyl-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)- alkyl, (C 1 -C7)-Al ky Ith io-(C 1 -C7)-al ky I , (Ci-C7)-Haloalkoxy-(Ci-C7)-alkyl, (Ci-C7)-Have meaning as defined below and wherein the arrow represents a bond to the 6-membered ring with the groupings A 1 , A 2 , A 3 , A 4 and A 5 , R 8 , R 9 , R 10 , R 11 , R 12, R 13, R 14, R 15, R 16, R 17, R 18 and R 19 are independently hydrogen, halogen, (Ci-C7) alkyl, (C 2 -C 7) alkenyl, ( C 2 -C 7) alkynyl, (Ci-C7) - haloalkyl, (C 2 -C 7) haloalkenyl, (C 2 -C 7) haloalkynyl, (C 3 -C 7) cycloalkyl, aryl, aryl- (Ci-C7) alkyl, heteroaryl, heteroaryl (Ci-C7) alkyl, (C 3 -C 7) cycloalkyl (Ci-C7) alkyl, heterocyclyl, heterocyclyl (Ci- C 7) alkyl, (Ci-C7) alkoxy (Ci-C7) - alkyl, (C 1 -C 7) -alkyl ky Ith io- (C 1 -C 7) -al ky I, ( Ci-C 7 ) -haloalkoxy- (Ci-C 7 ) -alkyl, (Ci-C 7 ) -
Haloalkylthio-(Ci-C7)-alkyl, COOR23 stehen, R5 und R6 mit dem Atom, an das sie gebunden sind, einen vollständig gesättigten, oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden, Haloalkylthio (C 1 -C 7 ) -alkyl, COOR 23 , R 5 and R 6 with the atom to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring,
R20 für Wasserstoff, (Ci-C7)-Alkyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (Ci-C7)-R 20 is hydrogen, (Ci-C7) alkyl, (C 2 -C 7) alkenyl, (C 2 -C 7) alkynyl, (Ci-C7) -
Haloalkyl, (C2-C7)-Haloalkenyl, (C2-C7)-Haloalkinyl, (C3-C7)-Cycloalkyl, (C -C7)- Cycloalkenyl, (Ci-C7)-Alkoxy, Aryl, Heteroaryl, Heterocyclyl, (Ci-C7)- Al kylcarbonyl , Aryl-(Ci -C7)-Al kylcarbonyl , (C3-C7)-Cycloal kylcarbonyl , Haloalkyl, (C 2 -C 7 ) -haloalkenyl, (C 2 -C 7 ) -haloalkynyl, (C 3 -C 7 ) -cycloalkyl, (C 7 -C 7 ) -cycloalkenyl, (C 1 -C 7 ) -alkoxy, aryl, heteroaryl, heterocyclyl, (Ci-C7) - Al kylcarbonyl, aryl (Ci-C7) Al kylcarbonyl, (C3-C 7) -Cycloal kylcarbonyl,
Arylcarbonyl, Heteroarylcarbonyl, (Ci-C7)-Alkoxycarbonyl, (C2-C7)- Alkenyloxycarbonyl, Aryl-(Ci-C7)-alkoxycarbonyl, Heteroaryl-(Ci-C7)- alkoxycarbonyl, (C3-C7)-Cycloalkyl-(Ci-C7)-alkoxycarbonyl, (Ci-C7)-Alkylsulfonyl, (Ci-C7)-Haloalkylsulfonyl, Arylsulfonyl, Heteroarylsulfonyl, (C3-C7)- Cycloalkylsulfonyl, (Ci-C7)-Alkylsulfinyl, Arylsulfinyl, Heteroarylsulfinyl, (C3-C7)- Cycloalkylsulfinyl steht, n für 0, 1 oder 2 steht Arylcarbonyl, heteroarylcarbonyl, (Ci-C 7) alkoxycarbonyl, (C 2 -C 7) - alkenyloxycarbonyl, aryl (Ci-C 7) alkoxycarbonyl, heteroaryl- (Ci-C7) - alkoxycarbonyl, (C3-C 7 ) -cycloalkyl- (Ci-C 7) alkoxycarbonyl, (Ci-C7) alkylsulfonyl, (Ci-C 7) haloalkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, (C3-C7) - cycloalkylsulfonyl, (Ci-C 7) alkylsulfinyl, arylsulfinyl, heteroarylsulfinyl, (C3-C7) - cycloalkylsulfinyl, n is 0, 1 or 2;
R21 und R22 gleich oder verschieden sind und unabhängig voneinander für R 21 and R 22 are the same or different and independently of each other
Wasserstoff, (Ci-C7)-Alkyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (Ci-C7)-Cyanoalkyl, (Ci-C7)-Haloalkyl, (C2-C7)-Haloalkenyl, (C2-C7)-Haloalkinyl, (C3-C7)-Cycloalkyl, (C3-C7)-Halocycloalkyl, (C -C7)-Cycloalkenyl, (C -C7)-Halocycloalkenyl, (Ci-C7)- Alkoxy-(Ci-C7)-alkyl, (Ci-C7)-Haloalkoxy-(Ci-C7)-alkyl, (Ci-C7)-Alkylthio-(Ci-C7)- alkyl, (Ci-C7)-Haloalkylthio-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)-haloalkyl, Aryl, Aryl-(Ci-C7)-alkyl, Heteroaryl, Heteroaryl-(Ci-C7)-alkyl, (C3-C7)-Cycloalkyl- (Ci-C7)-alkyl, (C4-C7)-Cycloalkenyl-(Ci-C7)-alkyl, COR23, SO2R24, -(Ci-C7)-Alkyl- HNO2S-, (C3-C7)-Cycloalkyl-HNO2S-, Heterocyclyl, (Ci-C7)-Alkoxycarbonyl- (Ci-C7)-alkyl, (Ci-C7)-Alkoxycarbonyl, Aryl-(Ci-C7)-Alkoxycarbonyl-(Ci-C7)-alkyl, Aryl-(Ci -C7)-Al koxycarbonyl , Heteroaryl-(Ci -C7)-Al koxycarbonyl , (C2-C7)- Al kenyloxycarbonyl , (C2-C7)-Al kinyloxycarbonyl , Heterocyclyl-(Ci -C7)-al kyl stehen Hydrogen, (Ci-C7) alkyl, (C 2 -C 7) alkenyl, (C 2 -C 7) alkynyl, (Ci-C 7) cyanoalkyl, (Ci-C7) haloalkyl, ( C 2 -C 7 ) -haloalkenyl, (C 2 -C 7 ) -haloalkynyl, (C 3 -C 7 ) -cycloalkyl, (C 3 -C 7 ) -halocycloalkyl, (C 2 -C 7 ) -cycloalkenyl, (C -C 7) -Halocycloalkenyl, (Ci-C7) - alkoxy (Ci-C7) alkyl, (Ci-C7) haloalkoxy (Ci-C7) alkyl, (Ci-C7) - alkylthio (Ci-C7) - alkyl, (Ci-C 7) -Haloalkylthio- (Ci-C7) alkyl, (Ci-C7) alkoxy (Ci-C7) haloalkyl, aryl, aryl - (Ci-C7) alkyl, heteroaryl, heteroaryl (Ci-C7) alkyl, (C 3 -C 7) cycloalkyl (Ci-C7) alkyl, (C 4 -C 7) - cycloalkenyl (C 7) alkyl, COR 23, SO 2 R 24, - (Ci-C7) alkyl- HNO 2 S-, (C 3 -C 7) cycloalkyl-HNO 2 S-, heterocyclyl , (C 1 -C 7 ) -alkoxycarbonyl- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxycarbonyl, aryl- (C 1 -C 7 ) -alkoxycarbonyl- (C 1 -C 7 ) -alkyl, aryl- (Ci-C7) Al koxycarbonyl, heteroaryl (Ci-C7) Al koxycarbonyl, (C 2 -C 7) - Al alkenyloxycarbonyl, (C 2 -C 7) -alkyl kinyloxycarbonyl, heterocyclyl (Ci -C 7 ) -al kyl stand s
R23 für Wasserstoff, (Ci-C7)-Alkyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (Ci-C7)-R 23 is hydrogen, (Ci-C7) alkyl, (C 2 -C 7) alkenyl, (C 2 -C 7) alkynyl, (Ci-C7) -
Cyanoalkyl, (Ci-C7)-Haloalkyl, (C2-C7)-Haloalkenyl, (C2-C7)-Haloalkinyl, (C3-C7)- Cycloalkyl, (C3-C7)-Halocycloalkyl, (C -C7)-Cycloalkenyl, (C -C7)- Halocycloalkenyl, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)-haloalkyl Aryl, Aryl-(Ci-C7)-alkyl, Heteroaryl, Heteroaryl-(Ci-C7)-alkyl, (C3-C7)-Cycloalkyl- (Ci -C7)-al kyl , (C -C7)-Cycloal kenyl-(Ci -C7)-al kyl , (Ci -C7)-Al koxycarbonyl- (Ci-C7)-alkyl, (C2-C7)-Alkenyloxycarbonyl-(Ci-C7)-alkyl, Aryl-(Ci-C7)- Al koxycarbonyl-(Ci -C7)-al kyl , Hydroxycarbonyl-(Ci -C7)-al kyl , Heterocyclyl , Heterocyclyl-(Ci-C7)-alkyl steht und Cyanoalkyl, (Ci-C7) haloalkyl, (C 2 -C 7) haloalkenyl, (C 2 -C 7) haloalkynyl, (C 3 -C 7) - cycloalkyl, (C 3 -C 7) halocycloalkyl , (C -C 7 ) -Cycloalkenyl, (C -C 7 ) - Halocycloalkenyl, (Ci-C7) alkoxy (Ci-C7) alkyl, (Ci-C7) alkoxy (Ci-C7) haloalkyl aryl, aryl (Ci-C7) alkyl, Heteroaryl, heteroaryl- (Ci-C 7 ) -alkyl, (C 3 -C 7 ) -cycloalkyl- (Ci -C 7 ) -alkenyl, (C -C 7 ) -Cycloal kenyl- (Ci -C 7 ) - al kyl, (Ci-C7) -alkyl koxycarbonyl- (Ci-C7) alkyl, (C 2 -C 7) -Alkenyloxycarbonyl- (Ci-C7) alkyl, aryl (Ci-C7) - Al koxycarbonyl- (C 1 -C 7 ) -alkyl, hydroxycarbonyl- (C 1 -C 7 ) -alkyl, heterocyclyl, heterocyclyl- (C 1 -C 7 ) -alkyl and
R24 für Wasserstoff, (Ci-C7)-Alkyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (Ci-C7)-R 24 is hydrogen, (Ci-C7) alkyl, (C 2 -C 7) alkenyl, (C 2 -C 7) alkynyl, (Ci-C7) -
Cyanoalkyl, (Ci-C7)-Haloalkyl, (C2-C7)-Haloalkenyl, (C2-C7)-Haloalkinyl, (C3-C7)- Cycloalkyl, (C3-C7)-Halocycloalkyl, (C -C7)-Cycloalkenyl, (C -C7)- Halocycloalkenyl, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)-haloalkyl Aryl, Aryl-(Ci-C7)-alkyl, Heteroaryl, Heteroaryl-(Ci-C7)-alkyl, Heterocyclyl- (Ci-C7)-alkyl, (C3-C7)-Cycloalkyl-(Ci-C7)-alkyl, (C -C7)-Cycloalkenyl-(Ci-C7)- alkyl, NR21R22 steht. Cyanoalkyl, (Ci-C7) haloalkyl, (C 2 -C 7) haloalkenyl, (C 2 -C 7) haloalkynyl, (C 3 -C 7) - cycloalkyl, (C 3 -C 7) halocycloalkyl , (C-C7) cycloalkenyl, (C -C 7) - (Halocycloalkenyl, (Ci-C7) alkoxy (Ci-C7) alkyl, (Ci-C7) alkoxy Ci-C 7) -haloalkyl aryl, aryl (Ci-C7) alkyl, heteroaryl, heteroaryl (Ci-C7) alkyl, heterocyclyl (Ci-C7) alkyl, (C 3 -C 7) cycloalkyl - (Ci-C 7 ) -alkyl, (C -C 7 ) -cycloalkenyl- (Ci-C 7 ) - alkyl, NR 21 R 22 .
Besonders bevorzugt sind Verbindungen der allgemeinen Formel (I), worin Particular preference is given to compounds of the general formula (I) in which
R1, R2 und R7 unabhängig voneinander für Wasserstoff, Halogen, Cyano, Nitro, R 1 , R 2 and R 7 independently of one another represent hydrogen, halogen, cyano, nitro,
NR21R22, OR23, S(O)nR24, Thiocyanato, Isothiocyanato, (Ci-C6)-Alkyl, (C2-C6)- Alkenyl, (C2-C6)-Alkinyl, (Ci-C6)-Haloalkyl, (C2-C6)-Haloalkenyl, (C2-C6)- Haloalkinyl, (C3-C6)-Cycloalkyl, (C3-C6)-Halocycloalkyl, (C4-C6)-Cycloalkenyl, (C4-C6)-Halocycloalkenyl, Pentafluorthio, (Ci-C6)-Alkoxy-(Ci-C6)-haloalkyl, NR 21 R 22, OR 23, S (O) n R 24, thiocyanato, isothiocyanato, (Ci-C 6) -alkyl, (C 2 -C 6) - alkenyl, (C 2 -C 6) -alkynyl, ( Ci-C 6) -haloalkyl, (C 2 -C 6) haloalkenyl, (C 2 -C 6) - haloalkynyl, (C3-C6) cycloalkyl, (C 3 -C 6) halocycloalkyl, (C 4 - C 6 ) cycloalkenyl, (C 4 -C 6) -halocycloalkenyl, pentafluorothio, (C 1 -C 6) -alkoxy- (C 1 -C 6) -haloalkyl,
(Ci-C6)-Haloalkoxy-(Ci-C6)-haloalkyl, (Ci-C6)-Haloalkoxy-(Ci-C6)-alkyl, Aryl, Aryl-(Ci-C6)-alkyl, Heteroaryl, Heteroaryl-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl- (Ci-C6)-alkyl, (C4-C6)-Cycloalkenyl-(Ci-C6)-alkyl, Heterocyclyl, Heterocyclyl- (Ci -C6)-al kyl , (Ci -C6)-Al koxy-(Ci -C6)-al kyl , (Ci-C6)-Al kylth io-(Ci -C6)-al kyl , (C 1 -C 6 ) -haloalkoxy- (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -haloalkoxy- (C 1 -C 6 ) -alkyl, aryl, aryl- (C 1 -C 6 ) -alkyl, heteroaryl, heteroaryl (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 4 -C 6 ) -cycloalkenyl- (C 1 -C 6 ) -alkyl, heterocyclyl, heterocyclyl- ( C 1 -C 6 ) -alcyl, (C 1 -C 6 ) -alkoxy (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkyl (C 1 -C 6 ) -alkyl,
(Ci-C6)-Haloalkylthio-(Ci-C6)-alkyl, (Ci-C6)-Alkylcarbonyl-(Ci-C6)-alkyl, COOR23 CONR21R22, COR23 , -C=NOR23, R21 R22N-(Ci-C6)-alkyl, R23OOC-(Ci-C6)-alkyl, Aryl-(Ci-C6)-alkinyl, Heteroaryl-(Ci-C6)-alkinyl, Heterocyclyl-(Ci-C6)-alkinyl, Tris- [(Ci-C6)-alkyl]silyl-(C2-C6)-alkinyl, Bis-[(Ci-C6)-alkyl](aryl)silyl-(C2-C6)-alkinyl, Bis-aryl[(Ci-C6)-alkyl]silyl-(C2-C6)-alkinyl, (C3-C6)-Cycloalkyl-(C2-C6)-alkinyl, Aryl (C2-C6)-al kenyl , Heteroaryl-(C2-C6)-al kenyl , Heterocyclyl-(C2-C6)-al kenyl , (C3-C6)-Cycloal kyl-(C2-C6)-al kenyl , (Ci -C6)-Al koxy-(Ci -C6)-al koxy-(Ci -C6)-al kyl , (Ci-C6)-Alkylaminosulfonylannino, (C3-C6)-Cycloalkylaminosulfonylannino, Diazo, Aryldiazo stehen, (Ci-C 6) -Haloalkylthio- (Ci-C 6) alkyl, (Ci-C6) alkylcarbonyl (Ci-C 6) alkyl, COOR 23 CONR 21 R 22, COR 23, -C = NOR 23 , R 21 R 22 is N- (C 1 -C 6 ) -alkyl, R 23 is OOC- (C 1 -C 6 ) -alkyl, aryl- (C 1 -C 6 ) -alkynyl, heteroaryl- (C 1 -C 6 ) -alkynyl, Heterocyclyl (C 1 -C 6 ) alkynyl, tris [(C 1 -C 6 ) alkyl] silyl (C 2 -C 6 ) alkynyl, bis [(C 1 -C 6 ) alkyl] (aryl) silyl ( C 2 -C 6 ) alkynyl, bis-aryl [(C 1 -C 6 ) alkyl] silyl (C 2 -C 6 ) alkynyl, (C 3 -C 6 ) cycloalkyl (C 2 -C 6 ) alkynyl, aryl (C 2 -C 6) alkenyl, heteroaryl (C 2 -C 6 ) alkenyl, heterocyclyl (C 2 -C 6 ) alkenyl, (C 3 -C 6 ) cycloalkyl (C C 2 -C 6 ) -alkenyl, (C 1 -C 6 ) -alkoxy (C 1 -C 6 ) -alkoxy (C 1 -C 6 ) -alkyl, (C 1 -C 6) -alkylaminosulfonylannino, (C 3 -C 6) -cycloalkylaminosulfonylannino, diazo, aryldiazo,
X1, X2 und X3 gleich oder verschieden sind und unabhängig voneinander für O X 1 , X 2 and X 3 are the same or different and are each independently O.
(Sauerstoff), S (Schwefel), N (Stickstoff), die Gruppierung C-R2 oder die (Oxygen), S (sulfur), N (nitrogen), the group CR 2 or the
Gruppierung N-R20 stehen, wobei jedoch in keinem Fall ein O- und S-Atom benachbart sind und wobei in keinem Fall jeweils mehr als ein O- oder S-Atom im gebildeten 5-gliedrigen Ring enthalten ist, und wobei R2 in der Gruppierung C-R2 und R20 in der Gruppierung N-R20 jeweils gleiche oder verschiedene Bedeutungen gemäß der oben- oder nachstehenden Definitionen haben, Grouping NR 20 are, but in no case adjacent to an O and S atom and in each case in each case more than one O or S atom in the formed 5-membered ring is contained, and wherein R 2 in the grouping CR 2 and R 20 in moiety NR 20 each have the same or different meanings according to the above or below definitions,
W für O (Sauerstoff) oder S (Schwefel) steht, W is O (oxygen) or S (sulfur),
A1, A2, A3, A4 und A5 gleich oder verschieden sind und unabhängig voneinander für N (Stickstoff) oder die Gruppierung C-R7 stehen, wobei jedoch in keinem Fall mehr als zwei N-Atome benachbart sind, und wobei R7 in der Gruppierung C-R7 jeweils gleiche oder verschiedene Bedeutungen gemäß der oben stehenden Definition hat, R3 für (Ci-C6)-Alkyl, Cyano-(Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (Ci-C6)- Haloalkyl, (C2-C6)-Haloalkenyl, (C2-C6)-Haloalkinyl, (C3-C6)-Cycloalkyl, (C3-C6)- Halocycloalkyl, (C4-C6)-Cycloalkenyl, (C4-C6)-Halocycloalkenyl, , Aryl, Aryl- (Ci-C6)-alkyl, Heteroaryl, Heteroaryl-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl-(Ci-C6)- alkyl, Heterocyclyl, Heterocyclyl-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, (C 1 -C6)-Al ky Ith io-(C 1 -C6)-al ky I , (Ci-C6)-Haloalkoxy-(Ci-C6)-alkyl, (Ci-C6)-A 1 , A 2 , A 3 , A 4 and A 5 are the same or different and are independently N (nitrogen) or the group CR 7 , but in no case more than two N atoms are adjacent, and wherein R 7 in the grouping CR 7 each has identical or different meanings according to the above definition, R 3 is (Ci-C 6) -alkyl, cyano- (Ci-C6) alkyl, (C 2 -C 6) alkenyl , (C 2 -C 6) alkynyl, (Ci-C 6) - haloalkyl, (C2-C6) haloalkenyl, (C2-C6) haloalkynyl, (C3-C6) -cycloalkyl, (C 3 -C 6) - halocycloalkyl, (C 4 -C 6) cycloalkenyl, (C 4 -C 6) -Halocycloalkenyl, aryl, aryl (Ci-C 6) alkyl, heteroaryl, heteroaryl (Ci-C 6) - alkyl, (C3-C6) cycloalkyl (Ci-C 6) - alkyl, heterocyclyl, heterocyclyl (Ci-C 6) alkyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, ( C 1 -C 6) -alkyl ky Ith io- (C 1 -C 6) -al ky I, (Ci-C 6) haloalkoxy (Ci-C 6) alkyl, (Ci-C 6) -
Haloalkylthio-(Ci-C6)-alkyl, R21R22N-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)- alkoxy-(Ci-C6)-alkyl steht, Haloalkylthio (C 1 -C 6 ) -alkyl, R 21 R 22 N- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) - alkyl,
R4 für Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (Ci-C6)- Haloalkyl, (C2-C6)-Haloalkenyl, (C2-C6)-Haloalkinyl, (C3-C6)-Cycloalkyl, (C3-C6)-R 4 represents hydrogen, (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) -alkynyl, (Ci-C 6) - haloalkyl, (C2-C6) - haloalkenyl, (C2-C6) haloalkynyl, (C3-C6) -cycloalkyl, (C 3 -C 6) -
Halocycloalkyl, (C4-C6)-Cycloalkenyl, (C4-C6)-Halocycloalkenyl, Aryl, Aryl- (Ci-C6)-alkyl, Heteroaryl, Heteroaryl-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl-(Ci-C6)- alkyl, Heterocyclyl, Heterocyclyl-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, Halocycloalkyl, (C 4 -C 6) -cycloalkenyl, (C 4 -C 6) -halocycloalkenyl, aryl, aryl- (C 1 -C 6 ) -alkyl, heteroaryl, heteroaryl- (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) ) -cycloalkyl- (Ci-C 6) - alkyl, heterocyclyl, heterocyclyl (Ci-C 6) alkyl, (Ci-C6) alkoxy (Ci-C 6) alkyl,
(Ci-C6)-Alkylthio-(Ci-C6)-alkyl, (Ci-C6)-Haloalkoxy-(Ci-C6)-alkyl, (Ci-C6)- Haloalkylthio-(Ci-C6)-alkyl, (Ci-C6)-Alkylamino-(Ci-C6)-alkyl, Bis-[(Ci-C6)- alkyl]amino-(Ci-C6)-alkyl, (C3-C6)-Cycloalkylamino-(Ci-C6)-alkyl, (Ci-Ce)-Alkoxy- (Ci-C6)-alkoxy-(Ci-C6)-alkyl, COR23, (Ci-C6)-Alkoxycarbonyl, (C2-C6)- Al kenyloxycarbonyl , (C2-C6)-Al kinyloxycarbonyl , Aryl-(Ci -C6)-al koxycarbonyl , Heteroaryl-(Ci-C6)-alkoxycarbonyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkoxycarbonyl, CONR21 R22, SO2R24, Hydroxycarbonyl-(Ci-C6)-alkyl, (Ci-C6)-Alkoxycarbonyl- (C1 -C6)-al kyl , (C2-C6)-Al kenyloxycarbonyl-(Ci -C6)-al kyl , (C2-C6)- Alkinyloxycarbonyl-(Ci-C6)-alkyl, Aryl-(Ci-C6)-alkoxycarbonyl-(Ci-C6)-alkyl, Heteroaryl-(Ci-C6)-alkoxycarbonyl-(Ci-C6)-alkyl, Heterocyclyl-(Ci-C6)- alkoxycarbonyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylcarbonyl-(Ci-C6)-alkyl, (Ci-C6)- Alkylsulfonyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylsulfinyl-(Ci-C6)-alkyl steht, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) - Haloalkylthio- (Ci-C 6) alkyl, (Ci-C6) alkylamino (Ci-C 6) alkyl, - bis [(Ci-C 6) - alkyl] amino- (Ci-C 6) alkyl , (C 3 -C 6) -cycloalkylamino- (C 1 -C 6) -alkyl, (C 1 -C 6) -alkoxy- (C 1 -C 6) -alkoxy- (C 1 -C 6 ) -alkyl, COR 23 , (C 1 -C 6 ) -alkyl) 6 ) -alkoxycarbonyl, (C 2 -C 6 ) -alkenyloxycarbonyl, (C 2 -C 6 ) -alkynyloxycarbonyl, aryl- (C 1 -C 6 ) -alkenoxycarbonyl, heteroaryl- (C 1 -C 6 ) -alkoxycarbonyl, (C 3 -C 6 ) ) -Cycloalkyl- (C 1 -C 6 ) -alkoxycarbonyl, CONR 21 R 22 , SO 2 R 24 , hydroxycarbonyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxycarbonyl- (C 1 -C 6 ) -alkyl, (C 2 -C 6) -alkyl kenyloxycarbonyl- (Ci-C6) -alkyl, (C 2 -C 6) - alkynyloxycarbonyl (Ci-C6) alkyl, aryl (Ci-C6) alkoxycarbonyl ( C 1 -C 6 ) -alkyl, heteroaryl- (C 1 -C 6 ) -alkoxycarbonyl- (C 1 -C 6 ) -alkyl, heterocyclyl- (C 1 -C 6 ) -alkoxycarbonyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) - alkylcarbonyl (Ci-C 6) alkyl, (Ci-C 6) - alkylsulfonyl (Ci-C 6) alkyl, (Ci-C6) alkylsulfinyl (Ci-C 6) -alkyl,
R5 und R6 unabhängig voneinander für Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (Ci-C6)-Haloalkyl, (C2-C6)-Haloalkenyl, (C2-C6)-Haloalkinyl, (C3-C6)-Cycloalkyl, (C3-C6)-Halocycloalkyl, (C -C6)-Cycloalkenyl, (C -C6)- Halocycloalkenyl, Aryl, Aryl-(Ci-C6)-alkyl, Heteroaryl, Heteroaryl-(Ci-C6)-alkyl, (C3-C6)-Cycloal kyl-(Ci -C6)-al kyl , Heterocyclyl , Heterocyclyl-(Ci -C6)-al kyl , (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkylthio-(Ci-C6)-alkyl, (Ci-Ce)-Haloalkoxy- (Ci-C6)-alkyl, (Ci-C6)-Haloalkylthio-(Ci-C6)-alkyl, COOR23, CONR21 R22, R 5 and R 6 independently of one another represent hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (C 1 -C 6 ) -haloalkyl, (C 2 -C 6 ) haloalkenyl, (C2-C6) haloalkynyl, (C3-C6) -cycloalkyl, (C3-C 6) halocycloalkyl, (C-C6) cycloalkenyl, (C-C6) - Halocycloalkenyl, aryl, Aryl- (C 1 -C 6) -alkyl, heteroaryl, heteroaryl- (C 1 -C 6) -alkyl, (C 3 -C 6) -cycloalkyl (C 1 -C 6) -alkyl, heterocyclyl, heterocyclyl- (C 1 -C 6) - al kyl, (Ci-C6) -alkoxy- (Ci-C 6 ) -alkyl, (Ci-C6) -alkylthio (Ci-C 6 ) -alkyl, (Ci-Ce) -haloalkoxy- (Ci-C 6 ) -alkyl, (C 1 -C 6 ) -haloalkylthio (C 1 -C 6 ) -alkyl, COOR 23 , CONR 21 R 22 ,
Hydroxycarbonyl-(Ci-C6)-alkyl, (Ci-C6)-Alkoxycarbonyl-(Ci-C6)-alkyl, (C2-C6)- Al kenyloxycarbonyl-(Ci -C6)-al kyl , (C2-C6)-Al kinyloxycarbonyl-(Ci -C6)-al kyl , Aryl- (Ci-C6)-alkoxycarbonyl-(Ci-C6)-alkyl, Heteroaryl-(Ci-C6)-alkoxycarbonyl-(Ci-C6)- al kyl , Heterocyclyl-(Ci -C6)-al koxycarbonyl-(Ci-C6)-al kyl stehen ,  Hydroxycarbonyl- (C 1 -C 6) -alkyl, (C 1 -C 6) -alkoxycarbonyl- (C 1 -C 6) -alkyl, (C 2 -C 6) -alkhenyloxycarbonyl- (C 1 -C 6) -alkyl, (C 2 -C 6) - Al kinyloxycarbonyl- (Ci -C6) -alkyl, aryl- (Ci-C6) -alkoxycarbonyl- (Ci-C6) -alkyl, heteroaryl- (Ci-C6) -alkoxycarbonyl- (Ci-C6) - al kyl, heterocyclyl - (C 1 -C 6) -alkoxycarbonyl- (C 1 -C 6) -alkyl,
R3 und R4 mit dem Stickstoffatom, an das sie gebunden sind, einen vollständig R 3 and R 4 with the nitrogen atom to which they are attached, a complete
gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3-7- gliedrigen Ring bilden,  form saturated, partially saturated or completely unsaturated, optionally interrupted by heteroatoms and optionally further substituted 3-7-membered ring,
R1 und X1 , wenn X1 für eine Gruppe C-R2 steht, mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig R 1 and X 1 , when X 1 is a group CR 2 , with the atoms to which they are attached, a fully saturated, partially saturated or completely
ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden, X1 und X2, wenn beide für eine Gruppe C-R2 stehen, mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden, form unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring, X 1 and X 2 , when both represent a group CR 2 , with the atoms to which they are attached form a fully saturated, partially saturated or fully unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring,
A1 und A2, wenn beide für eine Gruppe C-R7 stehen, mit den Atomen, an die sie A 1 and A 2 , when both represent a group CR 7 , with the atoms to which they belong
gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden,  form a fully saturated, partially saturated or fully unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring,
A2 und A3, wenn beide für eine Gruppe C-R7 stehen, mit den Atomen, an die sie A 2 and A 3 , when both represent a group CR 7 , with the atoms to which they belong
gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden und  form a fully saturated, partially saturated or fully unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5-7-membered ring and form
A3 und A4, wenn beide für eine Gruppe C-R7 stehen, mit den Atomen, an die sie A 3 and A 4 , when both represent a group CR 7 , with the atoms to which they belong
gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden,  form a fully saturated, partially saturated or fully unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring,
Y für eine Bindung oder für die Gruppierungen Y-1 bis Y-7 Y for a bond or for the groupings Y-1 to Y-7
steht, wobei R8, R9, R10, R1 1, R12, R13, R14, R15, R16, R17, R18 und R19 jeweils die , wherein R 8, R 9, R 10, R 1 1, R 12, R 13, R 14, R 15, R 16, R 17, R 18 and R 19 in each case the
Bedeutung gemäß der nachstehenden Definition haben und wobei der Pfeil für eine Bindung zum 6-gliedrigen Ring mit den Gruppierungen A1 , A2, A3, A4 und A5 steht, Have meaning as defined below and the arrow for is a bond to the 6-membered ring with the groups A 1 , A 2 , A 3 , A 4 and A 5 ,
R9, R10, R1 1 , R12, R13, R14, R15, R16, R17, R18 und R19 unabhängig voneinander für Wasserstoff, Fluor, Chlor, Brom, lod, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)- Alkinyl, (Ci-C6)-Haloalkyl, (C2-C6)-Haloalkenyl, (C2-C6)-Haloalkinyl, (C3-C6)- Cycloalkyl, Aryl, Aryl-(Ci-C6)-alkyl, Heteroaryl, Heteroaryl-(Ci-C6)-alkyl, (C3-C6)- Cycloalkyl-(Ci-C6)-alkyl, Heterocyclyl, Heterocyclyl-(Ci-C6)-alkyl, (Ci-Ce)-Alkoxy (Ci-C6)-alkyl, (Ci-C6)-Alkylthio-(Ci-C6)-alkyl, (Ci-C6)-Haloalkoxy-(Ci-C6)-alkyl, (Ci-C6)-Haloalkylthio-(Ci-C6)-alkyl, COOR23 stehen, und R6 mit dem Atom, an das sie gebunden sind, einen vollständig gesättigten, oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden, für Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (Ci-C6)- Haloalkyl, (C2-C6)-Haloalkenyl, (C2-C6)-Haloalkinyl, (C3-C6)-Cycloalkyl, (C -C6)- Cycloalkenyl, (Ci-C6)-Alkoxy, Aryl, Heteroaryl, Heterocyclyl, (C1-C6)- Al kylcarbonyl , Aryl-(Ci -C6)-Al kylcarbonyl , (C3-C6)-Cycloal kylcarbonyl , R 9, R 10, R 1 1, R 12, R 13, R 14, R 15, R 16, R 17, R 18 and R 19 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, (Ci-C 6) -alkyl, (C2-C6) alkenyl, (C 2 -C 6) - alkynyl, (Ci-C 6) -haloalkyl, (C2-C6) haloalkenyl, (C2-C6) haloalkynyl , (C 3 -C 6) - cycloalkyl, aryl, aryl (Ci-C 6) alkyl, heteroaryl, heteroaryl (Ci-C 6) alkyl, (C 3 -C 6) - cycloalkyl (Ci- C 6 ) -alkyl, heterocyclyl, heterocyclyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkylthio (C 1 -C 6 ) -alkyl, COOR 23 , and R 6 with the atom to which they are attached are, form a fully saturated, or partially saturated, optionally interrupted by hetero atoms and optionally further substituted 5-7-membered ring, is hydrogen, (Ci-C 6) -alkyl, (C2-C6) alkenyl, (C2-C 6) alkynyl, (Ci-C 6) - haloalkyl, (C2-C6) haloalkenyl, (C2-C6) haloalkynyl, (C3-C6) cycloalkyl, (C-C6) - Cy cloalkenyl, (C 1 -C 6) -alkoxy, aryl, heteroaryl, heterocyclyl, (C 1 -C 6) -alkylcarbonyl, aryl- (C 1 -C 6) -alkylcarbonyl, (C 3 -C 6) -cycloalkylcarbonyl,
Arylcarbonyl, Heteroarylcarbonyl, (Ci-C6)-Alkoxycarbonyl, (C2-C6)- Alkenyloxycarbonyl, Aryl-(Ci-C6)-alkoxycarbonyl, Heteroaryl-(Ci-Ce)- alkoxycarbonyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkoxycarbonyl, (Ci-C6)-Alkylsulfonyl (Ci-C6)-Haloalkylsulfonyl, Arylsulfonyl, Heteroarylsulfonyl, (C3-C6)- Cycloalkylsulfonyl, (Ci-C6)-Alkylsulfinyl, Arylsulfinyl, Heteroarylsulfinyl, (C3-C6)- Cycloalkylsulfinyl steht, für 0, 1 oder 2 steht und R22 gleich oder verschieden sind und unabhängig voneinander für Arylcarbonyl, heteroarylcarbonyl, (C 1 -C 6) -alkoxycarbonyl, (C 2 -C 6) -alkenyloxycarbonyl, aryl- (C 1 -C 6) -alkoxycarbonyl, heteroaryl- (C 1 -C 6) -alkoxycarbonyl, (C 3 -C 6) -cycloalkyl- (Ci -C 6) -alkoxycarbonyl, (C 1 -C 6) -alkylsulfonyl (C 1 -C 6) -haloalkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, (C 3 -C 6) -cycloalkylsulfonyl, (C 1 -C 6) -alkylsulfinyl, arylsulfinyl, heteroarylsulfinyl, (C 3 -C 6) - Cycloalkylsulfinyl, is 0, 1 or 2 and R 22 are identical or different and independently of one another
Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (Ci-C6)-Cyanoalkyl, (Ci-C6)-Haloalkyl, (C2-C6)-Haloalkenyl, (C2-C6)-Haloalkinyl, (C3-C6)-Cycloalkyl, (C3-C6)-Halocycloalkyl, (C4-C6)-Cycloalkenyl, (C4-C6)-Halocycloalkenyl, (C1-C6)- Alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Haloalkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkylthio-(Ci-C6) alkyl, (Ci-C6)-Haloalkylthio-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-haloalkyl, Aryl, Aryl-(Ci-C6)-alkyl, Heteroaryl, Heteroaryl-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl- (Ci-C6)-alkyl, (C4-C6)-Cycloalkenyl-(Ci-C6)-alkyl, COR23, SO2R24, -(Ci-C6)-Alkyl- HNO2S-, (C3-C6)-Cycloalkyl-HNO2S-, Heterocyclyl, (Ci-C6)-Alkoxycarbonyl- (Ci-C6)-alkyl, (Ci-C6)-Alkoxycarbonyl, Aryl-(Ci-C6)-Alkoxycarbonyl-(Ci-C6)-alkyl, Aryl-(Ci-C6)-Alkoxycarbonyl, Heteroaryl-(Ci-C6)-Alkoxycarbonyl, (C2-C6)-Hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (C 1 -C 6 ) -cyanoalkyl, (C 1 -C 6 ) -haloalkyl, (C 2 -C 6 ) -alkenyl, C 6) haloalkenyl, (C2-C6) haloalkynyl, (C3-C6) -cycloalkyl, (C3-C6) halocycloalkyl, (C 4 -C 6) cycloalkenyl, (C 4 -C 6) -Halocycloalkenyl, (C1-C6) - alkoxy- (Ci-C 6) alkyl, (Ci-C6) haloalkoxy (Ci-C 6) alkyl, (Ci-C6) alkylthio (Ci-C 6) alkyl, (C 1 -C 6 ) -haloalkylthio (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -haloalkyl, aryl, Aryl (Ci-C 6) alkyl, heteroaryl, heteroaryl (Ci-C 6) alkyl, (C3-C6) cycloalkyl (Ci-C 6) alkyl, (C 4 -C 6) - Cycloalkenyl- (C 1 -C 6 ) -alkyl, COR 23 , SO 2 R 24 , - (C 1 -C 6 ) -alkyl-HNO 2 S-, (C 3 -C 6 ) -cycloalkyl-HNO 2 S-, heterocyclyl, (C 1 -C 6 ) -Alkoxycarbonyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxycarbonyl, aryl- (C 1 -C 6 ) -alkoxycarbonyl- (C 1 -C 6 ) -alkyl, aryl- (C 1 -C 6 ) -alkoxycarbonyl , Heteroaryl- (C 1 -C 6) -alkoxycarbonyl, (C 2 -C 6) -
Al kenyloxycarbonyl , (C2-C6)-Al kinyloxycarbonyl , Heterocyclyl-(Ci -C6)-al kyl stehen Al kenyloxycarbonyl, (C2-C6) -Al kinyloxycarbonyl, heterocyclyl (Ci -C6) -alkyl stand
R23 für Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (Ci-C6)- Cyanoalkyl, (Ci-C6)-Haloalkyl, (C2-C6)-Haloalkenyl, (C2-C6)-Haloalkinyl, (C3-C6)-R 23 is hydrogen, (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) -alkynyl, (Ci-C 6) - cyanoalkyl, (Ci-C 6) - haloalkyl, (C2-C6) haloalkenyl, (C2-C6) haloalkynyl, (C 3 -C 6) -
Cycloalkyl, (C3-C6)-Halocycloalkyl, (C -C6)-Cycloalkenyl, (C -C6)- Halocycloalkenyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-haloalkyl, Aryl, Aryl-(Ci-C6)-alkyl, Heteroaryl, Heteroaryl-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl- (C1 -C6)-al kyl , (C -C6)-Cycloal kenyl-(Ci -C6)-al kyl , (C1 -C6)-Al koxycarbonyl- (Ci-C6)-alkyl, (C2-C6)-Alkenyloxycarbonyl-(Ci-C6)-alkyl, Aryl-(Ci-Ce)-Cycloalkyl, (C3-C 6) halocycloalkyl, (C-C6) cycloalkenyl, (C-C6) - Halocycloalkenyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, (Ci-C6 ) -Alkoxy- (C 1 -C 6 ) -haloalkyl, aryl, aryl- (C 1 -C 6 ) -alkyl, heteroaryl, heteroaryl- (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl- (Cl -C 6) -alkyl, (C-C6) -Cycloal kenyl- (Ci-C6) -alkyl, (C1-C6) -alkyl koxycarbonyl- (Ci-C 6) alkyl, (C2- C 6 ) alkenyloxycarbonyl- (C 1 -C 6 ) -alkyl, aryl- (C 1 -C 6 ) -
Al koxycarbonyl-(Ci -C6)-al kyl , Hydroxycarbonyl-(Ci -C6)-al kyl , Heterocyclyl , Heterocyclyl-(Ci-C6)-alkyl steht und Alkoxycarbonyl- (C 1 -C 6) -alkyl, hydroxycarbonyl- (C 1 -C 6) -alkyl, heterocyclyl, heterocyclyl- (C 1 -C 6) -alkyl and
R24 für Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (Ci-C6)- Cyanoalkyl, (Ci-C6)-Haloalkyl, (C2-C6)-Haloalkenyl, (C2-C6)-Haloalkinyl, (C3-C6)-R 24 is hydrogen, (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) -alkynyl, (Ci-C 6) - cyanoalkyl, (Ci-C 6) - haloalkyl, (C2-C6) haloalkenyl, (C2-C6) haloalkynyl, (C 3 -C 6) -
Cycloalkyl, (C3-C6)-Halocycloalkyl, (C -C6)-Cycloalkenyl, (C -C6)- Halocycloalkenyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-haloalkyl, Aryl, Aryl-(Ci-C6)-alkyl, Heteroaryl, Heteroaryl-(Ci-C6)-alkyl, Heterocyclyl- (Ci-C6)-alkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (C -C6)-Cycloalkenyl-(Ci-C6)- al kyl, NR21 R22 steht. Cycloalkyl, (C3-C 6) halocycloalkyl, (C-C6) cycloalkenyl, (C-C6) - Halocycloalkenyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, (Ci-C6 ) -Alkoxy- (C 1 -C 6 ) -haloalkyl, aryl, aryl- (C 1 -C 6 ) -alkyl, heteroaryl, heteroaryl- (C 1 -C 6 ) -alkyl, heterocyclyl- (C 1 -C 6 ) -alkyl, (C3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 6 -C 6 ) -cycloalkenyl- (C 1 -C 6 ) -alkyl, NR 21 R 22 .
Ganz besonders bevorzugt sind Verbindungen der allgemeinen Formel (I), worin Very particular preference is given to compounds of the general formula (I) in which
R1, R2 und R7 unabhängig voneinander für Wasserstoff, Fluor, Chlor, Brom, lod, R 1 , R 2 and R 7 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine,
Cyano, Nitro, NR21R22, OR23, S(O)nR24, Thiocyanato, Isothiocyanato, Methyl,Cyano, nitro, NR 21 R 22 , OR 23 , S (O) n R 24 , thiocyanato, isothiocyanato, methyl,
Ethyl, n-Propyl, 1 -Methylethyl, n-Butyl, 1 -Methyl propyl, 2-Methylpropyl, 1 ,1 - Dimethylethyl, n-Pentyl, 1 -Methylbutyl, 2-Methylbutyl, 3-Methylbutyl, 1 ,1 - Dimethylpropyl, 1 ,2-Dimethylpropyl, 2,2-Dimethylpropyl, 1 -Ethylpropyl, n-Hexyl, 1 -Methylpentyl, 2-Methylpentyl, 3-Methylpentyl, 4-Methylpentyl, 1 ,1 - Dimethylbutyl, 1 ,2-Dimethylbutyl, 1 ,3-Di-methylbutyl, 2,2-Dimethylbutyl, 2,3- Dimethylbutyl, 3,3-Dimethylbutyl, 1 -Ethylbutyl, 2-Ethylbutyl, 1 ,1 ,2- Trimethylpropyl, 1 ,2,2-Trinnethylpropyl, 1 -Ethyl-1 -methylpropyl und 1 -Ethyl-2- methylpropyl, Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl, Cyclohexylmethyl, gegebenenfalls substituiertes Phenyl, Heteroaryl, Ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1, 1-dimethylpropyl , 1, 2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1 - Dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1, 2,2-trinnethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, optionally substituted phenyl, heteroaryl,
Heterocyclyl, Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, , Spiro[2.2]pent 1 -yl, Spiro[2.3]hex-1 -yl, Spiro[2.3]hex-4-yl, 3-Spiro[2.3]hex-5-yl, Spiro[3.3]hept- 1 -yl, Spiro[3.3]hept-2-yl, Bicyclo[1 .1 .0]butan-1 -yl, Bicyclo[1 .1 .0]butan-2-yl, Bicyclo[2.1 .0]pentan-1 -yl, Bicyclo[1 .1 .1 ]pentan-1 -yl, Bicyclo[2.1 .0]pentan-2-yl, Bicyclo[2.1 .0]pentan-5-yl, Bicyclo[2.1 .1]hexyl, Bicyclo[2.2.1]hept-2-yl, Heterocyclyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, spiro [2.2] pent-1-yl, spiro [2.3] hex-1-yl, spiro [2.3] hex-4-yl, 3-spiro [2.3] hex-5- yl, spiro [3.3] hept-1-yl, spiro [3.3] hept-2-yl, bicyclo [1-1.0] butan-1-yl, bicyclo [1-1.0] butan-2-yl, Bicyclo [2.1.0] pentan-1-yl, bicyclo [1,11,1] pentan-1-yl, bicyclo [2.1.0] pentan-2-yl, bicyclo [2.1.0] pentan-5-yl, Bicyclo [2.1.1] hexyl, bicyclo [2.2.1] hept-2-yl,
Bicyclo[2.2.2]octan-2-yl, Bicyclo[3.2.1 ]octan-2-yl, Bicyclo[3.2.2]nonan-2-yl, Adamantan-1 -yl, Adamantan-2-yl, 1 -Methylcyclopropyl, 2-Methylcyclopropyl, 2,2-Dimethylcyclopropyl, 2,3-Dimethylcyclopropyl, 1 ,1 '-Bi(cyclopropyl)-1 -yl, 1 ,1 ' Bi(cyclopropyl)-2-yl, 2'-Methyl-1 ,1 '-bi(cyclopropyl)-2-yl, 1 -Cyanocyclopropyl, 2- Cyanocyclopropyl, 1 -Methylcyclobutyl, 2-Methylcyclobutyl, 3-Methylcyclobutyl, 1 -Cyanocyclobutyl, 2-Cyanocyclobutyl, 3-Cyanocyclobutyl, 1 -Allylcyclopropyl, 1 Vinylcyclobutyl, 1 -Vinylcyclopropyl, 1 -Ethylcyclopropyl, 1 -Methylcyclohexyl, 2- Methylcyclohexyl, 3-Methylcyclohexyl, 1 -Methoxycyclohexyl, 2- Methoxycyclohexyl, 3-Methoxycyclohexyl, Ethenyl, 1 -Propenyl, 2-Propenyl, 1 - Methyl-ethenyl, 1 -Butenyl, 2-Butenyl, 3-Butenyl, 1 -Methyl-1 -propenyl, 2-Methyl- 1 -propenyl, 1 -Methyl-2-propenyl, 2-Methyl-2-propenyl, 1 -Pentenyl, 2-Pentenyl, 3-Pentenyl, 4-Pentenyl, 1 -Methyl-1 -butenyl, 2-Methyl-1 -butenyl, 3-Methyl-1 - butenyl, 1 -Methyl-2-butenyl, 2-Methyl-2-butenyl, 3-Methyl-2-butenyl, 1 -Methyl-3 butenyl, 2-Methyl-3-butenyl, 3-Methyl-3-butenyl, 1 ,1 -Dimethyl-2-propenyl, 1 ,2- Dimethyl-1 -propenyl, 1 ,2-Dimethyl-2-propenyl, 1 -Ethyl-1 -propenyl, 1 -Ethyl-2- propenyl, 1 -Hexenyl, 2-Hexenyl, 3-Hexenyl, 4-Hexenyl, 5-Hexenyl, 1 -Methyl-1 - pentenyl, 2-Methyl-1 -pentenyl, 3-Methyl-1 -pentenyl, 4-Methyl-1 -pentenyl, 1 - Methyl-2-pentenyl, 2-Methyl-2-pentenyl, 3-Methyl-2-pentenyl, 4-Methyl-2- pentenyl, 1 -Methyl-3-pentenyl, 2-Methyl-3-pentenyl, 3-Methyl-3-pentenyl, 4- Methyl-3-pentenyl, 1 -Methyl-4-pentenyl, 2-Methyl-4-pentenyl, 3-Methyl-4- pentenyl, 4-Methyl-4-pentenyl, 1 ,1 -Dimethyl-2-butenyl, 1 ,1 -Dimethyl-3-butenyl, 1 ,2-Dimethyl-1 -butenyl, 1 ,2-Dimethyl-2-butenyl, 1 ,2-Dimethyl-3-butenyl, 1 ,3- Dimethyl-1 -butenyl, 1 ,3-Dimethyl-2-butenyl, 1 ,3-Dimethyl-3-butenyl, 2,2- Dimethyl-3-butenyl, 2,3-Dimethyl-1 -butenyl, 2,3-Dimethyl-2-butenyl, 2,3- Dimethyl-3-butenyl, 3,3-Dimethyl-l -butenyl, 3,3-Dimethyl-2-butenyl, 1 -Ethyl-1 - butenyl, 1 -Ethyl-2-butenyl, 1 -Ethyl-3-butenyl, 2-Ethyl-1 -butenyl, 2-Ethyl-2- butenyl, 2-Ethyl-3-butenyl, 1 ,1 ,2-Trimethyl-2-propenyl, 1 -Ethyl-1 -methyl-2- propenyl, 1 -Ethyl-2-methyl-1 -propenyl und 1 -Ethyl-2-methyl-2-propenyl, Ethinyl,Bicyclo [2.2.2] octan-2-yl, bicyclo [3.2.1] octan-2-yl, bicyclo [3.2.2] nonan-2-yl, adamantan-1-yl, adamantan-2-yl, 1 - Methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, 2,3-dimethylcyclopropyl, 1,1'-bis (cyclopropyl) -1-yl, 1,1 ', bi (cyclopropyl) -2-yl, 2'-methyl 1, 1 '-bi (cyclopropyl) -2-yl, 1-cyanocyclopropyl, 2-cyanocyclopropyl, 1-methylcyclobutyl, 2-methylcyclobutyl, 3-methylcyclobutyl, 1-cyanocyclobutyl, 2-cyanocyclobutyl, 3-cyanocyclobutyl, 1-allylcyclopropyl, 1 vinylcyclobutyl, 1-vinylcyclopropyl, 1-ethylcyclopropyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 1-methoxycyclohexyl, 2-methoxycyclohexyl, 3-methoxycyclohexyl, ethenyl, 1-propenyl, 2-propenyl, 1-methyl-ethenyl , 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2 Pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-bute nyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, 1-dimethyl-2-propenyl, 1, 2-dimethyl-1 -propenyl, 1, 2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1 -Methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl 2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4 -pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1, 1-dimethyl-2-butenyl, 1, 1-dimethyl-3-butenyl, 1, 2 -Dimethyl-1-butenyl, 1, 2-dimethyl-2-butenyl, 1, 2-dimethyl-3-butenyl, 1, 3-dimethyl-1-butenyl, 1, 3-dimethyl-2-butenyl, 1, 3 Dimethyl 3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3- Dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1, 1, 2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1 - Ethyl 2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl, ethynyl,
1 - Propinyl, 2-Propinyl, 1 -Butinyl, 2-Butinyl, 3-Butinyl, 1 -Methyl-2-propinyl, 1 - Pentinyl, 2-Pentinyl, 3-Pentinyl, 4-Pentinyl, 1 -Methyl-2-butinyl, 1 -Methyl-3- butinyl, 2-Methyl-3-butinyl, 3-Methyl-1 -butinyl, 1 ,1 -Dimethyl-2-propinyl, 1 -Ethyl-1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2- butinyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, 1-ethyl
2- propinyl, 1 -Hexinyl, 2-Hexinyl, 3-Hexinyl, 4-Hexinyl, 5-Hexinyl, 1 -Methyl-2- pentinyl, 1 -Methyl-3-pentinyl, 1 -Methyl-4-pentinyl, 2-Methyl-3-pentinyl, 2-Methyl- 4-pentinyl, 3-Methyl-1 -pentinyl, 3-Methyl-4-pentinyl, 4-Methyl-1 -pentinyl, 4- Methyl-2-pentinyl, 1 ,1 -Dimethyl-2-butinyl, 1 ,1 -Dimethyl-3-butinyl, 1 ,2-Dimethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2- Methyl 3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1, 1 - Dimethyl-2-butynyl, 1, 1-dimethyl-3-butynyl, 1, 2-dimethyl
3- butinyl, 2,2-Dimethyl-3-butinyl, 3,3-Dimethyl-1 -butinyl, 1 -Ethyl-2-butinyl, 1 - Ethyl-3-butinyl, 2-Ethyl-3-butinyl, 1 -Ethyl-1 -methyl-2-propinyl, Methoxymethyl, Ethoxymethyl, Ethoxyethyl, Methoxyethyl, Methoxy-n-propyl, Ethoxy-n-propyl, Methoxybutyl, Methoxy-iso-Propyl, iso-Propoxymethyl, iso-Propoxyethyl, Thfluormethyl, Pentafluorethyl, 1 ,1 ,2,2-Tetrafluorethyl, Heptafluorpropyl, Nonafluorbutyl, Chlordifluormethyl, Bromdifluormethyl, Dichlorfluormethyl, loddifluormethyl, Bromfluormethyl, 1 -Fluorethyl, 2-Fluorethyl, Fluormethyl, Difluormethyl, 2,2-Difluorethyl, 2,2,2-Thfluorethyl, Difluor-tert.-butyl, 3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1 - Ethyl 1-methyl-2-propynyl, methoxymethyl, ethoxymethyl, ethoxyethyl, methoxyethyl, methoxy-n-propyl, ethoxy-n-propyl, methoxybutyl, methoxy-isopropyl, iso-propoxymethyl, iso-propoxyethyl, thfluoromethyl, pentafluoroethyl, 1, 1, 2,2-tetrafluoroethyl, heptafluoropropyl, nonafluorobutyl, chlorodifluoromethyl, bromodifluoromethyl, dichlorofluoromethyl, iododifluoromethyl, bromofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, fluoromethyl, difluoromethyl, 2,2-difluoroethyl, 2,2,2-thfluoroethyl, difluoro-tert.-butyl,
Thfluormethoxymethyl, Thfluormethoxyethyl, Trifluormethoxy-n-propyl, Thfluoromethoxymethyl, thfluoromethoxyethyl, trifluoromethoxy-n-propyl,
Difluormethoxymethyl, Difluormethoxyethyl, Difluormethoxy-n-propyl, 2,2- Difluorethoxymethyl, 2,2-Difluorethoxyethyl, 2,2-Difluorethoxy-n-propyl, 2,2,2- Thfluorethoxymethyl, 2,2,2-Thfluorethoxyethyl, 2,2,2-Trifluorethoxy-n-propyl, Pentafluorethoxymethyl, Pentafluorethoxyethyl, Pentafluorethoxy-n-propyl, Methylthiomethyl, Methylthioethyl, Ethylthioethyl, Methylthio-n-propyl, Ethylthio- n-propyl, Trifluormethylthiomethyl, Trifluormethylthioethyl, Trifluormethylthio-n- propyl, 1 -Cyclobutenyl, 2-Cyclobutenyl, 1 -Cyclopentenyl, 2-Cyclopentenyl, 3- Cyclopentenyl, oder 1 -Cyclohexenyl, 2-Cyclohexenyl, 3-Cyclohexenyl, 1 ,3- Cyclohexadienyl oder 1 ,4-Cyclohexadienyl, Methoxymethoxymethyl, Difluoromethoxymethyl, difluoromethoxyethyl, difluoromethoxy-n-propyl, 2,2-difluoroethoxymethyl, 2,2-difluoroethoxyethyl, 2,2-difluoroethoxy-n-propyl, 2,2,2-thfluoroethoxymethyl, 2,2,2-thfluoroethoxyethyl, 2, 2,2-trifluoroethoxy-n-propyl, pentafluoroethoxymethyl, pentafluoroethoxyethyl, pentafluoroethoxy-n-propyl, methylthiomethyl, methylthioethyl, ethylthioethyl, methylthio-n-propyl, ethylthio-n-propyl, trifluoromethylthiomethyl, trifluoromethylthioethyl, trifluoromethylthio-n-propyl, 1 - Cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1, 3-cyclohexadienyl or 1, 4-cyclohexadienyl, methoxymethoxymethyl,
Methoxyethoxymethyl, Methoxyethoxyethyl, Methoxymethoxyethyl, Ethoxy-n- propoxymethyl, Ethoxy-n-propoxyethyl, Ethoxyethoxymethyl, Ethoxyethoxyethyl (C2-C6)-Haloalkenyl, (C2-C6)-Haloalkinyl, Pentafluorthio, Aryl-(Ci-C6)-alkyl, Heteroaryl-(Ci-C6)-alkylHeterocyclyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylcarbonyl- (Ci-C6)-alkyl, COOR23, CONR21 R22, COR23 , -C=NOR23, R21 R22N-(Ci-C6)-alkyl, R23OOC-(Ci-C6)-alkyl, Aryl-(Ci -Ce)-al kinyl , Heteroaryl-(Ci-C6)-alkinyl, Methoxyethoxymethyl, methoxyethoxyethyl, methoxymethoxyethyl, ethoxy-n-propoxymethyl, ethoxy-n-propoxyethyl, ethoxyethoxymethyl, ethoxyethoxyethyl (C 2 -C 6 ) -haloalkenyl, (C 2 -C 6 ) -haloalkynyl, pentafluorothio, aryl- (C 1 -C 6 ) - alkyl, heteroaryl- (C 1 -C 6 ) -alkyl-heterocyclyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylcarbonyl- (C 1 -C 6 ) -alkyl, COOR 23 , CONR 21 R 22 , COR 23 , -C = NOR 23 , R 21 R 22 N- (C 1 -C 6 ) -alkyl, R 23 is OOC- (C 1 -C 6 ) -alkyl, aryl- (C 1 -C 6 ) -alkenyl, heteroaryl- (C 1 -C 6 ) -alkynyl,
Heterocyclyl-(Ci-C6)-alkinyl, Trimethylsilylethinyl, Triethylsilylethinyl, Tris-(iso- propyl)silylethinyl, (C3-C6)-Cycloalkyl-(C2-C6)-alkinyl, Aryl-(C2-C6)-alkenyl, Heteroaryl-(C2-C6)-alkenyl, Heterocyclyl-(C2-C6)-alkenyl, (C3-C6)-Cycloalkyl- (C2-C6)-alkenyl, (Ci-C6)-Alkylaminosulfonylannino, (C3-C6)- Heterocyclyl (C 1 -C 6) alkynyl, trimethylsilylethynyl, triethylsilylethynyl, tris (isopropyl) silylethynyl, (C 3 -C 6) -cycloalkyl- (C 2 -C 6) -alkynyl, aryl- (C 2 -C 6) -alkenyl, heteroaryl (C2-C6) -alkenyl, heterocyclyl- (C2-C6) -alkenyl, (C3-C6) -cycloalkyl- (C2-C6) -alkenyl, (Ci-C6) -alkylaminosulfonylannino, (C3-C6) -
Cycloalkylaminosulfonylannino, Diazo, Aryldiazo, Trimethylsilyl, Triethylsilyl, Tris- (iso-propyl)silyl, Diphenyl(methyl)silyl, Dimethyl(phenyl)silyl, Dimethyl(tert.- butyl)silyl, Diphenyl(tert.-butyl)silyl stehen, X1, X2 und X3 gleich oder verschieden sind und unabhängig voneinander für O Cycloalkylaminosulfonylannino, diazo, aryldiazo, trimethylsilyl, triethylsilyl, tris (iso-propyl) silyl, diphenyl (methyl) silyl, dimethyl (phenyl) silyl, dimethyl (tert-butyl) silyl, diphenyl (tert-butyl) silyl, X 1 , X 2 and X 3 are the same or different and are each independently O.
(Sauerstoff), S (Schwefel), N (Stickstoff), die Gruppierung C-R2 oder die (Oxygen), S (sulfur), N (nitrogen), the group CR 2 or the
Gruppierung N-R20 stehen, wobei jedoch in keinem Fall ein O- und S-Atom benachbart sind und wobei in keinem Fall jeweils mehr als ein O- oder S-Atom im gebildeten 5-gliedrigen Ring enthalten ist, und wobei R2 in der Gruppierung C-R2 und R20 in der Gruppierung N-R20 jeweils gleiche oder verschiedeneGrouping NR 20 are, but in no case adjacent to an O and S atom and in each case in each case more than one O or S atom in the formed 5-membered ring is contained, and wherein R 2 in the grouping CR 2 and R 20 in the grouping NR 20 are the same or different
Bedeutungen gemäß der oben- oder nachstehenden Definitionen haben, Have meanings according to the above or below definitions,
W für O (Sauerstoff) oder S (Schwefel) steht, A1, A2, A3, A4 und A5 gleich oder verschieden sind und unabhängig voneinander für N (Stickstoff) oder die Gruppierung C-R7 stehen, wobei jedoch in keinem Fall mehr als zwei N-Atome benachbart sind, und wobei R7 in der Gruppierung C-R7 jeweils gleiche oder verschiedene Bedeutungen gemäß der oben stehenden Definition hat, W is O (oxygen) or S (sulfur), A 1 , A 2 , A 3 , A 4 and A 5 are the same or different and independently of one another represent N (nitrogen) or the group CR 7 , but in none If more than two N atoms are adjacent, and R 7 in the group CR 7 has the same or different meanings as defined above,
R3 für Methyl, Ethyl, n-Propyl, 1 -Methylethyl, n-Butyl, 1 -Methylpropyl, 2-R 3 is methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-
Methylpropyl, 1 ,1 -Dimethylethyl, n-Pentyl, 1 -Methylbutyl, 2-Methylbutyl, 3- Methylbutyl, 1 ,1 -Dimethylpropyl, 1 ,2-Dimethylpropyl, 2,2-Dimethylpropyl, 1 - Ethylpropyl, n-Hexyl, 1 -Methylpentyl, 2-Methylpentyl, 3-Methylpentyl, 4- Methyl pentyl, 1 ,1 -Dimethylbutyl, 1 ,2-Dimethylbutyl, 1 ,3-Di-methylbutyl, 2,2-Methylpropyl, 1, 1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2.2-
Dimethylbutyl, 2,3-Dimethylbutyl, 3,3-Dimethylbutyl, 1 -Ethylbutyl, 2-Ethylbutyl, 1 ,1 ,2-Trimethylpropyl, 1 ,2,2-Trimethylpropyl, 1 -Ethyl-1 -methylpropyl und 1 - Ethyl-2-methylpropyl, Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl, Cyclohexylmethyl, Cyanomethyl, Cyanoethyl, Cyano-n-propyl, Cyano-n-butyl, Ethenyl, 1 -Propenyl, 2-Propenyl, 1 -Methyl-ethenyl, 1 -Butenyl, 2-Butenyl, 3- Butenyl, 1 -Methyl-1 -propenyl, 2-Methyl-1 -propenyl, 1 -Methyl-2-propenyl, 2- Methyl-2-propenyl, 1 -Pentenyl, 2-Pentenyl, 3-Pentenyl, 4-Pentenyl, 1 -Methyl-1 - butenyl, 2-Methyl-1 -butenyl, 3-Methyl-1 -butenyl, 1 -Methyl-2-butenyl, 2-Methyl-2- butenyl, 3-Methyl-2-butenyl, 1 -Methyl-3-butenyl, 2-Methyl-3-butenyl, 3-Methyl-3- butenyl, 1 ,1 -Dimethyl-2-propenyl, 1 ,2-Dimethyl-l -propenyl, 1 ,2-Dimethyl-2- propenyl, 1 -Ethyl-1 -propenyl, 1 -Ethyl-2-propenyl, 1 -Hexenyl, 2-Hexenyl, 3- Hexenyl, 4-Hexenyl, 5-Hexenyl, 1 -Methyl-1 -pentenyl, 2-Methyl-1 -pentenyl, 3- Methyl-1 -pentenyl, 4-Methyl-1 -pentenyl, 1 -Methyl-2-pentenyl, 2-Methyl-2- pentenyl, 3-Methyl-2-pentenyl, 4-Methyl-2-pentenyl, 1 -Methyl-3-pentenyl, 2- Methyl-3-pentenyl, 3-Methyl-3-pentenyl, 4-Methyl-3-pentenyl, 1 -Methyl-4- pentenyl, 2-Methyl-4-pentenyl, 3-Methyl-4-pentenyl, 4-Methyl-4-pentenyl, 1 ,1 - Dimethyl-2-butenyl, 1 ,1 -Dimethyl-3-butenyl, 1 ,2-Dimethyl-1 -butenyl, 1 ,2- Dimethyl-2-butenyl, 1 ,2-Dimethyl-3-butenyl, 1 ,3-Dimethyl-1 -butenyl, 1 ,3- Dimethyl-2-butenyl, 1 ,3-Dimethyl-3-butenyl, 2,2-Dimethyl-3-butenyl, 2,3- Dimethyl-1 -butenyl, 2,3-Dimethyl-2-butenyl, 2,3-Dimethyl-3-butenyl, 3,3- Dimethyl-1 -butenyl, 3,3-Dimethyl-2-butenyl, 1 -Ethyl-1 -butenyl, 1 -Ethyl-2-butenyl, 1 -Ethyl-3-butenyl, 2-Ethyl-1 -butenyl, 2-Ethyl-2-butenyl, 2-Ethyl-3-butenyl, 1 ,1 ,2- Trinnethyl-2-propenyl, 1 -Ethyl-1 -methyl-2-propenyl, 1 -Ethyl-2-methyl-1 -propenyl und 1 -Ethyl-2-methyl-2-propenyl, Ethinyl, 1 -Propinyl, 2-Propinyl, 1 -Butinyl, 2- Butinyl, 3-Butinyl, 1 -Methyl-2-propinyl, 1 -Pentinyl, 2-Pentinyl, 3-Pentinyl, 4- Pentinyl, 1 -Methyl-2-butinyl, 1 -Methyl-3-butinyl, 2-Methyl-3-butinyl, 3-Methyl-1 - butinyl, 1 ,1 -Dimethyl-2-propinyl, 1 -Ethyl-2-propinyl, 1 -Hexinyl, 2-Hexinyl, 3- Hexinyl, 4-Hexinyl, 5-Hexinyl, 1 -Methyl-2-pentinyl, 1 -Methyl-3-pentinyl, 1 - Methyl-4-pentinyl, 2-Methyl-3-pentinyl, 2-Methyl-4-pentinyl, 3-Methyl-1 -pentinyl, 3-Methyl-4-pentinyl, 4-Methyl-1 -pentinyl, 4-Methyl-2-pentinyl, 1 ,1 -Dimethyl-2- butinyl, 1 ,1 -Dimethyl-3-butinyl, 1 ,2-Dimethyl-3-butinyl, 2,2-Dimethyl-3-butinyl, 3,3-Dimethyl-1 -butinyl, 1 -Ethyl-2-butinyl, 1 -Ethyl-3-butinyl, 2-Ethyl-3-butinyl, 1 - Ethyl-1 -methyl-2-propinyl, T fluormethyl, Pentafluorethyl, 1 ,1 ,2,2- Tetrafluorethyl, Heptafluorpropyl, Nonafluorbutyl, Chlordifluormethyl, Dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2-trimethylpropyl, 1, 2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl- 2-methylpropyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyanomethyl, cyanoethyl, cyano-n-propyl, cyano-n-butyl, Ethenyl, 1-propenyl, 2-propenyl, 1-methyl-ethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2- propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, 1-dimethyl-2-propenyl, 1, 2-dimethyl-1-propenyl, 1, 2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2- Hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl 2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3 pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1, 1-dimethyl-2 butenyl, 1, 1-dimethyl-3-butenyl, 1, 2-Dimethyl-1-butenyl, 1, 2-dimethyl-2-butenyl, 1, 2-dimethyl-3-butenyl, 1, 3-dimethyl-1-butenyl, 1, 3-dimethyl-2-butenyl, 1, 3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3, 3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1, 1, 2-trinethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1 - propenyl and 1-ethyl-2-methyl-2-propenyl, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2- Pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2- propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl 4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pent inyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1, 1-dimethyl-2-butynyl, 1, 1-dimethyl-3-butynyl, 1, 2 Dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl, T fluoromethyl, pentafluoroethyl, 1,1,2,2-tetrafluoroethyl, heptafluoropropyl, nonafluorobutyl, chlorodifluoromethyl,
Bromdifluormethyl, Dichlorfluormethyl, loddifluormethyl, Bromfluormethyl, 1 - Fluorethyl, 2-Fluorethyl, Fluormethyl, Difluormethyl, 1 ,1 -Difluorethyl, 2,2- Difluorethyl, 2,2,2-Thfluorethyl, 3,3-Difluor-n-propyl, 3,3,3-Thfluor-n-propyl, 4,4- Difluor-n-butyl, 4,4,4-Thfluor-n-butyl, Difluor-tert.-butyl, Methoxymethyl, Ethoxymethyl, Ethoxyethyl, Methoxyethyl, Methoxy-n-propyl, Ethoxy-n-propyl, Methoxybutyl, Methoxy-iso-Propyl, iso-Propoxymethyl, iso-Propoxyethyl, Trifluormethoxymethyl, Trifluormethoxyethyl, Trifluormethoxy-n-propyl, Bromodifluoromethyl, dichlorofluoromethyl, iododifluoromethyl, bromofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, fluoromethyl, difluoromethyl, 1,1-difluoroethyl, 2,2-difluoroethyl, 2,2,2-thfluoroethyl, 3,3-difluoro-n-propyl, 3,3,3-thfluoro-n-propyl, 4,4-difluoro-n-butyl, 4,4,4-thfluoro-n-butyl, difluoro-tert-butyl, methoxymethyl, Ethoxymethyl, ethoxyethyl, methoxyethyl, methoxy-n-propyl, ethoxy-n-propyl, methoxybutyl, methoxy-isopropyl, iso-propoxymethyl, iso-propoxyethyl, trifluoromethoxymethyl, trifluoromethoxyethyl, trifluoromethoxy-n-propyl,
Difluormethoxymethyl, Difluormethoxyethyl, Difluormethoxy-n-propyl, 2,2- Difluorethoxymethyl, 2,2-Difluorethoxyethyl, 2,2-Difluorethoxy-n-propyl, 2,2,2- Trifluorethoxymethyl, 2,2,2-Trifluorethoxyethyl, 2,2,2-Trifluorethoxy-n-propyl, Pentafluorethoxymethyl, Pentafluorethoxyethyl, Pentafluorethoxy-n-propyl, Methylthiomethyl, Methylthioethyl, Ethylthioethyl, Methylthio-n-propyl, Ethylthio- n-propyl, Trifluormethylthiomethyl, Trifluormethylthioethyl, Trifluormethylthio-n- propyl, 1 -Cyclobutenyl, 2-Cyclobutenyl, 1 -Cyclopentenyl, 2-Cyclopentenyl, 3- Cyclopentenyl, oder 1 -Cyclohexenyl, 2-Cyclohexenyl, 3-Cyclohexenyl, 1 ,3- Cyclohexadienyl oder 1 ,4-Cyclohexadienyl, Methoxymethoxymethyl, Difluoromethoxymethyl, difluoromethoxyethyl, difluoromethoxy-n-propyl, 2,2-difluoroethoxymethyl, 2,2-difluoroethoxyethyl, 2,2-difluoroethoxy-n-propyl, 2,2,2-trifluoroethoxymethyl, 2,2,2-trifluoroethoxyethyl, 2, 2,2-trifluoroethoxy-n-propyl, pentafluoroethoxymethyl, pentafluoroethoxyethyl, pentafluoroethoxy-n-propyl, methylthiomethyl, methylthioethyl, ethylthioethyl, methylthio-n-propyl, ethylthio-n-propyl, trifluoromethylthiomethyl, trifluoromethylthioethyl, trifluoromethylthio-n-propyl, 1 - Cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1, 3-cyclohexadienyl or 1, 4-cyclohexadienyl, methoxymethoxymethyl,
Methoxyethoxymethyl, Methoxyethoxyethyl, Methoxymethoxyethyl, Ethoxy-n- propoxymethyl, Ethoxy-n-propoxyethyl, Ethoxyethoxymethyl, Ethoxyethoxyethyl, Methoxyethoxy-n-propyl, Ethoxyethoxy-n-propyl, Cyclopropylmethyl, Methoxyethoxymethyl, methoxyethoxyethyl, methoxymethoxyethyl, ethoxy-n-propoxymethyl, ethoxy-n-propoxyethyl, ethoxyethoxymethyl, ethoxyethoxyethyl, methoxyethoxy-n-propyl, ethoxyethoxy-n-propyl, cyclopropylmethyl,
Cyclobutylmethyl, Cyclopentylmethyl, Cyclohexylmethyl, Cyclopropyl, Cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropyl,
Cyclobutyl, Cyclopentyl, Cyclohexyl, Spiro[2.2]pent-1 -yl, Spiro[2.3]hex-1 -yl, Spiro[2.3]hex-4-yl, 3-Spiro[2.3]hex-5-yl, Spiro[3.3]hept-1 -yl, Spiro[3.3]hept-2-yl, Bicyclo[1 .1 .0]butan-1 -yl, Bicyclo[1 .1 .0]butan-2-yl, Bicyclo[2.1 .0]pentan-1 -yl, Bicyclo[1 .1 .1 ]pentan-1 -yl, Bicyclo[2.1 .0]pentan-2-yl, Bicyclo[2.1 .0]pentan-5-yl, Bicyclo[2.1 .1 ]hexyl, Bicyclo[2.2.1 ]hept-2-yl, Bicyclo[2.2.2]octan-2-yl, Cyclobutyl, cyclopentyl, cyclohexyl, spiro [2.2] pent-1-yl, spiro [2.3] hex-1-yl, spiro [2.3] hex-4-yl, 3-spiro [2.3] hex-5-yl, spiro [ 3.3] hept-1-yl, spiro [3.3] hept-2-yl, bicyclo [1-1.0] butan-1-yl, bicyclo [1-1.0] butan-2-yl, bicyclo [2.1. 0] pentan-1-yl, bicyclo [1,11,1] pentan-1-yl, bicyclo [2.1.0] pentan-2-yl, bicyclo [2.1.0] pentan-5-yl, bicyclo [2.1. 1] hexyl, bicyclo [2.2.1] hept-2-yl, bicyclo [2.2.2] octan-2-yl,
Bicyclo[3.2.1 ]octan-2-yl, Bicyclo[3.2.2]nonan-2-yl, Adamantan-1 -yl, Adamantan- 2-yl, 1 -Methylcyclopropyl, 2-Methylcyclopropyl, 2,2-Dimethylcyclopropyl, 2,3- Dimethylcyclopropyl, 1 ,1 '-Bi(cyclopropyl)-1 -yl, 1 ,1 '-Bi(cyclopropyl)-2-yl, 2'- Methyl-1 ,1 '-bi(cyclopropyl)-2-yl, (C2-C6)-Haloalkenyl, (C2-C6)-Haloalkinyl, gegebenenfalls substituiertes Phenyl, Aryl-(Ci-C6)-alkyl, Heteroaryl, Heteroaryl- (Ci-C6)-alkyl, Heterocyclyl, Heterocyclyl-(Ci-C6)-alkyl, R21R22N-(Ci-C6)-alkyl steht, für Wasserstoff, Methyl, Ethyl, n-Propyl, 1 -Methylethyl, n-Butyl, 1 -Methylpropyl, 2-Methylpropyl, 1 ,1 -Dimethylethyl, n-Pentyl, 1 -Methylbutyl, 2-Methylbutyl, 3- Methylbutyl, 1 ,1 -Dimethylpropyl, 1 ,2-Dimethylpropyl, 2,2-Dimethylpropyl, 1 - Ethylpropyl, n-Hexyl, 1 -Methylpentyl, 2-Methylpentyl, 3-Methylpentyl, 4- Methylpentyl, 1 ,1 -Dimethylbutyl, 1 ,2-Dimethylbutyl, 1 ,3-Di-methylbutyl, 2,2- Dimethylbutyl, 2,3-Dimethylbutyl, 3,3-Dimethylbutyl, 1 -Ethylbutyl, 2-Ethylbutyl, 1 ,1 ,2-Trimethylpropyl, 1 ,2,2-Trimethylpropyl, 1 -Ethyl-1 -methylpropyl und 1 - Ethyl-2-methylpropyl, Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl, Cyclohexylmethyl, Cyanomethyl, Cyanoethyl, Cyano-n-propyl, Cyano-n-butyl, Ethenyl, 1 -Propenyl, 2-Propenyl, 1 -Methyl-ethenyl, 1 -Butenyl, 2-Butenyl, 3- Butenyl, 1 -Methyl-1 -propenyl, 2-Methyl-1 -propenyl, 1 -Methyl-2-propenyl, 2- Methyl-2-propenyl, 1 -Pentenyl, 2-Pentenyl, 3-Pentenyl, 4-Pentenyl, 1 -Methyl-1 - butenyl, 2-Methyl-1 -butenyl, 3-Methyl-1 -butenyl, 1 -Methyl-2-butenyl, 2-Methyl-2- butenyl, 3-Methyl-2-butenyl, 1 -Methyl-3-butenyl, 2-Methyl-3-butenyl, 3-Methyl-3- butenyl, 1 ,1 -Dimethyl-2-propenyl, 1 ,2-Dimethyl-1 -propenyl, 1 ,2-Dimethyl-2- propenyl, 1 -Ethyl-1 -propenyl, 1 -Ethyl-2-propenyl, 1 -Hexenyl, 2-Hexenyl, 3- Hexenyl, 4-Hexenyl, 5-Hexenyl, 1 -Methyl-1 -pentenyl, 2-Methyl-1 -pentenyl, 3- Methyl-1 -pentenyl, 4-Methyl-1 -pentenyl, 1 -Methyl-2-pentenyl, 2-Methyl-2- pentenyl, 3-Methyl-2-pentenyl, 4-Methyl-2-pentenyl, 1 -Methyl-3-pentenyl, 2- Methyl-3-pentenyl, 3-Methyl-3-pentenyl, 4-Methyl-3-pentenyl, 1 -Methyl-4- pentenyl, 2-Methyl-4-pentenyl, 3-Methyl-4-pentenyl, 4-Methyl-4-pentenyl, 1 ,1 - Dimethyl-2-butenyl, 1 ,1 -Dimethyl-3-butenyl, 1 ,2-Dimethyl-1 -butenyl, 1 ,2- Dimethyl-2-butenyl, 1 ,2-Dimethyl-3-butenyl, 1 ,3-Dimethyl-1 -butenyl, 1 ,3- Dimethyl-2-butenyl, 1 ,3-Dimethyl-3-butenyl, 2,2-Dimethyl-3-butenyl, 2,3- Dimethyl-1 -butenyl, 2,3-Dimethyl-2-butenyl, 2,3-Dimethyl-3-butenyl, 3,3- Dimethyl-1 -butenyl, 3,3-Dimethyl-2-butenyl, 1 -Ethyl-1 -butenyl, 1 -Ethyl-2-butenyl, 1 -Ethyl-3-butenyl, 2-Ethyl-1 -butenyl, 2-Ethyl-2-butenyl, 2-Ethyl-3-butenyl, 1 ,1 ,2- Trinnethyl-2-propenyl, 1 -Ethyl-1 -methyl-2-propenyl, 1 -Ethyl-2-methyl-1 -propenyl und 1 -Ethyl-2-methyl-2-propenyl, Ethinyl, 1 -Propinyl, 2-Propinyl, 1 -Butinyl, 2- Butinyl, 3-Butinyl, 1 -Methyl-2-propinyl, 1 -Pentinyl, 2-Pentinyl, 3-Pentinyl, 4- Pentinyl, 1 -Methyl-2-butinyl, 1 -Methyl-3-butinyl, 2-Methyl-3-butinyl, 3-Methyl-1 - butinyl, 1 ,1 -Dimethyl-2-propinyl, 1 -Ethyl-2-propinyl, 1 -Hexinyl, 2-Hexinyl, 3- Hexinyl, 4-Hexinyl, 5-Hexinyl, 1 -Methyl-2-pentinyl, 1 -Methyl-3-pentinyl, 1 - Methyl-4-pentinyl, 2-Methyl-3-pentinyl, 2-Methyl-4-pentinyl, 3-Methyl-1 -pentinyl, 3-Methyl-4-pentinyl, 4-Methyl-1 -pentinyl, 4-Methyl-2-pentinyl, 1 ,1 -Dimethyl-2- butinyl, 1 ,1 -Dimethyl-3-butinyl, 1 ,2-Dimethyl-3-butinyl, 2,2-Dimethyl-3-butinyl, 3,3-Dimethyl-1 -butinyl, 1 -Ethyl-2-butinyl, 1 -Ethyl-3-butinyl, 2-Ethyl-3-butinyl, 1 - Ethyl-1 -methyl-2-propinyl, T fluormethyl, Pentafluorethyl, 1 ,1 ,2,2- Tetrafluorethyl, Heptafluorpropyl, Nonafluorbutyl, Chlordifluormethyl, Bromdifluormethyl, Dichlorfluormethyl, loddifluormethyl, Bromfluormethyl, 1 - Fluorethyl, 2-Fluorethyl, Fluormethyl, Difluormethyl, 2,2-Difluorethyl, 2,2,2- Trifluorethyl, 3,3,3-Trifluor-n-propyl, Difluor-tert.-butyl, (C2-C6)-Haloalkenyl, (C2-C6)-Haloalkinyl, 1 -Cyclobutenyl, 2-Cyclobutenyl, 1 -Cyclopentenyl, 2- Cyclopentenyl, 3-Cyclopentenyl, oder 1 -Cyclohexenyl, 2-Cyclohexenyl, 3- Cyclohexenyl, 1 ,3-Cyclohexadienyl oder 1 ,4-Cyclohexadienyl, Bicyclo [3.2.1] octan-2-yl, bicyclo [3.2.2] nonan-2-yl, adamantan-1-yl, adamantan-2-yl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, 2,3-Dimethylcyclopropyl, 1,1 '-Bi (cyclopropyl) -1-yl, 1,1' -Bi (cyclopropyl) -2-yl, 2'-methyl-1,1 '-bi (cyclopropyl) -2 -yl, (C 2 -C 6 ) -haloalkenyl, (C 2 -C 6 ) -haloalkynyl, optionally substituted phenyl, aryl- (C 1 -C 6 ) -alkyl, heteroaryl, heteroaryl- (C 1 -C 6 ) -alkyl, heterocyclyl, Heterocyclyl (C 1 -C 6 ) -alkyl, R 21 R 22 is N- (C 1 -C 6 ) -alkyl, represents hydrogen, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n- Hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2.2- Dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2-trimethylpropyl, 1, 2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl- 2-methylpropyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyanomethyl, cyanoethyl, cyano-n-propyl, cyano-n-butyl, ethenyl, 1-propenyl, 2-propenyl, 1-methyl-ethenyl, 1-butenyl, 2- Butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2- butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, 1-dimethyl-2-propenyl, 1, 2-dimethyl-1-propenyl, 1, 2 Dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl , 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3 Methyl 3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1, 1 - Dimethyl-2-butenyl, 1, 1-dimethyl-3-butenyl, 1, 2-dimethyl-1-butenyl, 1, 2-dimethyl-2-butenyl, 1, 2-dimethyl-3-butenyl, 1, 3 Dimethyl 1-butenyl, 1, 3-dimethyl-2-butenyl, 1, 3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2.3 -Dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2 -butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1, 1, 2-trinnethyl-2-propenyl, 1-ethyl 1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl , 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl , 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, 1-ethyl-2-propynyl , 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3 pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1, 1-dimethyl-2 - butynyl, 1, 1-dimethyl-3-butynyl, 1, 2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl , 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl, T fluoromethyl, pentafluoroethyl, 1,1,2,2-tetrafluoroethyl, heptafluoropropyl, nonafluorobutyl, chlorodifluoromethyl, Bromodifluoromethyl, dichlorofluoromethyl, iododifluoromethyl, bromofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, fluoromethyl, difluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 3,3,3-trifluoro-n-propyl, difluoro-tert. -butyl, (C 2 -C 6) -haloalkenyl, (C 2 -C 6) -haloalkynyl, 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2-cyclohexenyl, 3 Cyclohexenyl, 1, 3-cyclohexadienyl or 1, 4-cyclohexadienyl,
Methoxymethoxymethyl, Methoxyethoxymethyl, Methoxyethoxyethyl, Methoxymethoxymethyl, methoxyethoxymethyl, methoxyethoxyethyl,
Methoxymethoxyethyl, Ethoxy-n-propoxymethyl, Ethoxy-n-propoxyethyl, Methoxymethoxyethyl, ethoxy-n-propoxymethyl, ethoxy-n-propoxyethyl,
Ethoxyethoxymethyl, Ethoxyethoxyethyl, Methoxyethoxy-n-propyl, Ethoxyethoxymethyl, ethoxyethoxyethyl, methoxyethoxy-n-propyl,
Ethoxyethoxy-n-propyl, Cyclopropylmethyl, Cyclobutylmethyl, Ethoxyethoxy-n-propyl, cyclopropylmethyl, cyclobutylmethyl,
Cyclopentylmethyl, Cyclohexylmethyl, Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Spiro[2.2]pent-1 -yl, Spiro[2.3]hex-1 -yl, Spiro[2.3]hex-4-yl, 3- Spiro[2.3]hex-5-yl, Spiro[3.3]hept-1 -yl, Spiro[3.3]hept-2-yl, Bicyclo[1 .1 .0]butan-1 - yl, Bicyclo[1 .1 .0]butan-2-yl, Bicyclo[2.1 .0]pentan-1 -yl, Bicyclo[1 .1 .1 ]pentan-1 -yl, Bicyclo[2.1 .0]pentan-2-yl, Bicyclo[2.1 .0]pentan-5-yl, Bicyclo[2.1 .1]hexyl, Cyclopentylmethyl, cyclohexylmethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, spiro [2.2] pent-1-yl, spiro [2.3] hex-1-yl, spiro [2.3] hex-4-yl, 3-spiro [2.3] hexyl 5-yl, spiro [3.3] hept-1-yl, spiro [3.3] hept-2-yl, bicyclo [1-1.0] butan-1-yl, bicyclo [1-1.0] butane-2- yl, bicyclo [2.1.0] pentan-1-yl, bicyclo [1,11,1] pentan-1-yl, bicyclo [2.1.0] pentan-2-yl, bicyclo [2.1.0] pentane-5 yl, bicyclo [2.1.1] hexyl,
Bicyclo[2.2.1 ]hept-2-yl, Bicyclo[2.2.2]octan-2-yl, Bicyclo[3.2.1 ]octan-2-yl, Bicyclo[3.2.2]nonan-2-yl, Adamantan-1 -yl, Adamantan-2-yl, 1 - Methylcyclopropyl, 2-Methylcyclopropyl, 2,2-Dimethylcyclopropyl, 2,3- Dimethylcyclopropyl, 1 ,1 '-Bi(cyclopropyl)-1 -yl, 1 ,1 '-Bi(cyclopropyl)-2-yl, 2'- Methyl-1 ,1 '-bi(cyclopropyl)-2-yl, (C3-C6)-Halocycloalkyl, (C -C6)- Halocycloalkenyl, gegebenenfalls substituiertes Phenyl, Aryl-(Ci-C6)-alkyl, Heteroaryl, Heteroaryl-(Ci-C6)-alkyl, Heterocyclyl-(Ci-C6)-alkyl, Methoxymethyl, Ethoxymethyl, Ethoxyethyl, Methoxyethyl, Methoxy-n-propyl, Ethoxy-n-propyl, Methoxybutyl, Methoxy-iso-Propyl, iso-Propoxymethyl, iso-Propoxyethyl, Trifluormethoxymethyl, Trifluormethoxyethyl, Trifluormethoxy-n-propyl, Bicyclo [2.2.1] hept-2-yl, bicyclo [2.2.2] octan-2-yl, bicyclo [3.2.1] octan-2-yl, bicyclo [3.2.2] nonan-2-yl, adamantane 1 -yl, adamantan-2-yl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, 2,3-dimethylcyclopropyl, 1,1'-bis (cyclopropyl) -1-yl, 1,1 '-Bi (cyclopropyl) -2-yl, 2'-methyl-1, 1 '-bi (cyclopropyl) -2-yl, (C3-C 6) halocycloalkyl, (C-C6) - Halocycloalkenyl, optionally substituted phenyl, aryl, - (C 1 -C 6) -alkyl, heteroaryl, heteroaryl- (C 1 -C 6) -alkyl, heterocyclyl- (C 1 -C 6) -alkyl, methoxymethyl, ethoxymethyl, ethoxyethyl, methoxyethyl, methoxy-n-propyl, ethoxy-n-propyl , Methoxybutyl, methoxy-isopropyl, iso-propoxymethyl, isopropoxyethyl, trifluoromethoxymethyl, trifluoromethoxyethyl, trifluoromethoxy-n-propyl,
Difluormethoxymethyl, Difluormethoxyethyl, Difluormethoxy-n-propyl, 2,2- Difluorethoxymethyl, 2,2-Difluorethoxyethyl, 2,2-Difluorethoxy-n-propyl, 2,2,2- Trifluorethoxymethyl, 2,2,2-Trifluorethoxyethyl, 2,2,2-Trifluorethoxy-n-propyl, Pentafluorethoxymethyl, Pentafluorethoxyethyl, Pentafluorethoxy-n-propyl, Methylthiomethyl, Methylthioethyl, Ethylthioethyl, Methylthio-n-propyl, Ethylthio- n-propyl, Trifluormethylthiomethyl, Trifluormethylthioethyl, Trifluormethylthio-n- propyl, (Ci-C5)-Alkylamino-(Ci-C5)-alkyl, Bis-[(Ci-C5)-alkyl]amino-(Ci-C5)-alkyl, (C3-C6)-Cycloal kylam ino-(Ci -C5)-al kyl , (Ci -C5)-Al koxy-(Ci -C5)-al koxy-(Ci -C5)- alkyl, COR23, (Ci-C5)-Alkoxycarbonyl, (C2-C6)-Alkenyloxycarbonyl, (C2-C6)- AI kinyloxycarbonyl , Aryl-(Ci-Cs)-al koxycarbonyl , Heteroaryl-(Ci -C5)- alkoxycarbonyl, (C3-C6)-Cycloalkyl-(Ci-C5)-alkoxycarbonyl, CONR21R22, SO2R24, Hydroxycarbonyl-(Ci-C5)-alkyl, (Ci-C5)-Alkoxycarbonyl-(Ci-C5)-alkyl, (C2-C6)- Al kenyloxycarbonyl-(Ci -C6)-al kyl , (C2-C6)-Al kinyloxycarbonyl-(Ci-Cs)-al kyl , Aryl- (Ci-C5)-alkoxycarbonyl-(Ci-C5)-alkyl, Heteroaryl-(Ci-C5)-alkoxycarbonyl-(Ci-C5)- alkyl, Heterocyclyl-(Ci-C5)-alkoxycarbonyl-(Ci-C5)-alkyl, (Ci-CsJ-Alkylcarbonyl- (Ci-C5)-alkyl, (Ci-C5)-Alkylsulfonyl-(Ci-C5)-alkyl, (Ci-C5)-Alkylsulfinyl-(Ci-C5)- alkyl steht, R6 unabhängig voneinander für Wasserstoff, Methyl, Ethyl, n-Propyl, 1 - Methylethyl, n-Butyl, 1 -Methyl propyl, 2-Methylpropyl, 1 ,1 -Dimethylethyl, n- Pentyl, 1 -Methylbutyl, 2-Methylbutyl, 3-Methylbutyl, 1 ,1 -Dimethylpropyl, 1 ,2- Dimethylpropyl, 2,2-Dimethylpropyl, 1 -Ethylpropyl, n-Hexyl, 1 -Methylpentyl, 2- Methylpentyl, 3-Methylpentyl, 4-Methylpentyl, 1 ,1 -Dimethylbutyl, 1 ,2- Dimethylbutyl, 1 ,3-Di-methylbutyl, 2,2-Dimethylbutyl, 2,3-Dimethylbutyl, 3,3- Dimethylbutyl, 1 -Ethylbutyl, 2-Ethylbutyl, 1 ,1 ,2-Trimethyl propyl, 1 ,2,2- Trimethylpropyl, 1 -Ethyl-1 -methylpropyl und 1 -Ethyl-2-methylpropyl, Difluoromethoxymethyl, difluoromethoxyethyl, difluoromethoxy-n-propyl, 2,2-difluoroethoxymethyl, 2,2-difluoroethoxyethyl, 2,2-difluoroethoxy-n-propyl, 2,2,2-trifluoroethoxymethyl, 2,2,2-trifluoroethoxyethyl, 2, 2,2-trifluoroethoxy-n-propyl, pentafluoroethoxymethyl, pentafluoroethoxyethyl, pentafluoroethoxy-n-propyl, methylthiomethyl, methylthioethyl, ethylthioethyl, methylthio-n-propyl, ethylthio-n-propyl, trifluoromethylthiomethyl, trifluoromethylthioethyl, trifluoromethylthio-n-propyl, (Ci -C 5 ) -alkylamino- (C 1 -C 5 ) -alkyl, bis - [(C 1 -C 5 ) -alkyl] amino- (C 1 -C 5 ) -alkyl, (C 3 -C 6 ) -cycloalkylamino ( Ci-C5) -alkyl, (Ci-C5) -alkyl alkoxy- (Ci-C5) -al alkoxy- (Ci-C5) - alkyl, COR 23, (Ci-C 5) alkoxycarbonyl, (C2-C6) alkenyloxycarbonyl, (C 2 -C 6) - Al kinyloxycarbonyl, aryl- (C 1 -C 5 ) -alkenoxycarbonyl, heteroaryl- (C 1 -C 5 ) -alkoxycarbonyl, (C 3 -C 6) -cycloalkyl- (C 1 -C 5 ) -alkoxycarbonyl, CONR 21 R 22 , SO 2 R 24 , Hydroxycarbonyl- (C 1 -C 5) -alkyl, (C 1 -C 5) -alkoxycarbonyl- (C 1 -C 5) -alkyl, (C 2 -C 6) -alkhenyloxycarbonyl- (C 1 -C 6) -alkyl, (C 2 -C 6) - Al kinyloxycarbonyl- (C 1 -C 5) -alkyl, aryl- (C 1 -C 5) -alkoxycarbonyl- (C 1 -C 5) -alkyl, heteroaryl- (C 1 -C 5) -alkoxycarbonyl- (C 1 -C 5) -alkyl, heterocyclyl- (C 1 -C 5 ) -alkoxycarbonyl- (C 1 -C 5 ) -alkyl, (C 1 -C 5 -alkylcarbonyl- (C 1 -C 5 ) -alkyl, (C 1 -C 5 ) -alkylsulfonyl- (C 1 -C 5 ) -alkyl, ( C 1 -C 5 ) -alkylsulfinyl- (C 1 -C 5 ) -alkyl, R 6 independently of one another are hydrogen, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1 , 1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl , 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1 , 3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl,
Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl, Cyclohexylmethyl, Cyanonnethyl, Cyanoethyl, Cyano-n-propyl, Cyano-n-butyl, Ethenyl, 1 -Propenyl, 2-Propenyl, 1 -Methyl-ethenyl, 1 -Butenyl, 2-Butenyl, 3-Butenyl, 1 -Methyl-1 - propenyl, 2-Methyl-1 -propenyl, 1 -Methyl-2-propenyl, 2-Methyl-2-propenyl, 1 - Pentenyl, 2-Pentenyl, 3-Pentenyl, 4-Pentenyl, 1 -Methyl-1 -butenyl, 2-Methyl-1 - butenyl, 3-Methyl-1 -butenyl, 1 -Methyl-2-butenyl, 2-Methyl-2-butenyl, 3-Methyl-2- butenyl, 1 -Methyl-3-butenyl, 2-Methyl-3-butenyl, 3-Methyl-3-butenyl, 1 ,1 - Dimethyl-2-propenyl, 1 ,2-Dimethyl-1 -propenyl, 1 ,2-Dimethyl-2-propenyl, 1 -Ethyl- 1 -propenyl, 1 -Ethyl-2-propenyl, 1 -Hexenyl, 2-Hexenyl, 3-Hexenyl, 4-Hexenyl, 5- Hexenyl, 1 -Methyl-1 -pentenyl, 2-Methyl-1 -pentenyl, 3-Methyl-1 -pentenyl, 4- Methyl-1 -pentenyl, 1 -Methyl-2-pentenyl, 2-Methyl-2-pentenyl, 3-Methyl-2- pentenyl, 4-Methyl-2-pentenyl, 1 -Methyl-3-pentenyl, 2-Methyl-3-pentenyl, 3- Methyl-3-pentenyl, 4-Methyl-3-pentenyl, 1 -Methyl-4-pentenyl, 2-Methyl-4- pentenyl, 3-Methyl-4-pentenyl, 4-Methyl-4-pentenyl, 1 ,1 -Dimethyl-2-butenyl, 1 ,1 - Dimethyl-3-butenyl, 1 ,2-Dimethyl-1 -butenyl, 1 ,2-Dimethyl-2-butenyl, 1 ,2- Dimethyl-3-butenyl, 1 ,3-Dimethyl-1 -butenyl, 1 ,3-Dimethyl-2-butenyl, 1 ,3- Dimethyl-3-butenyl, 2,2-Dimethyl-3-butenyl, 2,3-Dimethyl-1 -butenyl, 2,3- Dimethyl-2-butenyl, 2,3-Dimethyl-3-butenyl, 3,3-Dimethyl-1 -butenyl, 3,3- Dimethyl-2-butenyl, 1 -Ethyl-1 -butenyl, 1 -Ethyl-2-butenyl, 1 -Ethyl-3-butenyl, 2- Ethyl-1 -butenyl, 2-Ethyl-2-butenyl, 2-Ethyl-3-butenyl, 1 ,1 ,2-Trimethyl-2-propenyl,Cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyanoethyl, cyanoethyl, cyano-n-propyl, cyano-n-butyl, ethenyl, 1-propenyl, 2-propenyl, 1-methyl-ethenyl, 1-butenyl, 2-butenyl, 3 Butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1 - Methyl 3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1, 2-dimethyl-1-propenyl, 1, 2-dimethyl-2 propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl- 1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2 pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4 -pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1, 1-dimethyl-2-butenyl, 1, 1-dimethyl-3-butenyl, 1, 2 -Dimethyl-1-butenyl, 1, 2-dimethyl-2-butenyl, 1, 2-dimethyl-3-butenyl, 1, 3-dimethyl-1-butenyl, 1, 3-dimethyl-2-butenyl, 1, 3 Dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3- Dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2- butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1, 1, 2-trimethyl-2-propenyl,
1 - Ethyl-1 -methyl-2-propenyl, 1 -Ethyl-2-methyl-1 -propenyl und 1 -Ethyl-2-methyl-1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl
2- propenyl, Ethinyl, 1 -Propinyl, 2-Propinyl, 1 -Butinyl, 2-Butinyl, 3-Butinyl, 1 - Methyl-2-propinyl, 1 -Pentinyl, 2-Pentinyl, 3-Pentinyl, 4-Pentinyl, 1 -Methyl-2- butinyl, 1 -Methyl-3-butinyl, 2-Methyl-3-butinyl, 3-Methyl-1 -butinyl, 1 ,1 -Dimethyl-2-propenyl, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl
2- propinyl, 1 -Ethyl-2-propinyl, 1 -Hexinyl, 2-Hexinyl, 3-Hexinyl, 4-Hexinyl, 5- Hexinyl, 1 -Methyl-2-pentinyl, 1 -Methyl-3-pentinyl, 1 -Methyl-4-pentinyl, 2-Methyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1 - Methyl 4-pentynyl, 2-methyl
3- pentinyl, 2-Methyl-4-pentinyl, 3-Methyl-1 -pentinyl, 3-Methyl-4-pentinyl, 4- Methyl-1 -pentinyl, 4-Methyl-2-pentinyl, 1 ,1 -Dimethyl-2-butinyl, 1 ,1 -Dimethyl-3- butinyl, 1 ,2-Dimethyl-3-butinyl, 2,2-Dimethyl-3-butinyl, 3,3-Dimethyl-1 -butinyl, 1 - Ethyl-2-butinyl, 1 -Ethyl-3-butinyl, 2-Ethyl-3-butinyl, 1 -Ethyl-1 -methyl-2-propinyl, Thfluormethyl, Pentafluorethyl, 1 ,1 ,2,2-Tetrafluorethyl, Heptafluorpropyl, 3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1, 1-dimethyl 2-butynyl, 1, 1-dimethyl-3-butynyl, 1, 2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2- butinyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl, thfluoromethyl, pentafluoroethyl, 1,1,2,2-tetrafluoroethyl, heptafluoropropyl,
Nonafluorbutyl, Chlordifluormethyl, Bromdifluormethyl, Dichlorfluormethyl, loddifluormethyl, Bromfluormethyl, 1 -Fluorethyl, 2-Fluorethyl, Fluormethyl, Difluormethyl, 1 ,1 -Difluorethyl, 2,2-Difluorethyl, 2,2,2-Trifluorethyl, 3,3,3-Trifluor- n-propyl, Difluor-tert.-butyl, (C2-C6)-Haloalkenyl, (C2-C6)-Haloalkinyl, (C3-C6)- Cycloalkyl, (C3-C6)-Halocycloalkyl, (C -C6)-Cycloalkenyl, (C -C6)- Halocycloalkenyl, Aryl, Aryl-(Ci-C5)-alkyl, Heteroaryl, Heteroaryl-(Ci-C5)-alkyl, Heterocyclyl, Heterocyclyl-(Ci-C5)-alkyl, Methoxymethyl, Ethoxymethyl, Nonafluorobutyl, chlorodifluoromethyl, bromodifluoromethyl, dichlorofluoromethyl, iododifluoromethyl, bromofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, fluoromethyl, difluoromethyl, 1,1-difluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 3,3,3- trifluoro-n-propyl, difluoro-tert-butyl, (C2-C6) haloalkenyl, (C2-C6) haloalkynyl, (C 3 -C 6) - cycloalkyl, (C3-C 6) halocycloalkyl, (C -C 6 ) -cycloalkenyl, (C -C 6 ) -halocycloalkenyl, aryl, aryl- (C 1 -C 5 ) -alkyl, heteroaryl, heteroaryl- (C 1 -C 5 ) -alkyl, heterocyclyl, heterocyclyl- (C 1 -C 5 ) -alkyl, methoxymethyl, ethoxymethyl,
Ethoxyethyl, Methoxyethyl, Methoxy-n-propyl, Ethoxy-n-propyl, Methoxybutyl, Methoxy-iso-Propyl, iso-Propoxymethyl, iso-Propoxyethyl, Ethoxyethyl, methoxyethyl, methoxy-n-propyl, ethoxy-n-propyl, methoxy-butyl, methoxy-isopropyl, iso-propoxymethyl, iso-propoxyethyl,
Trifluormethoxymethyl, Trifluormethoxyethyl, Trifluormethoxy-n-propyl, Trifluoromethoxymethyl, trifluoromethoxyethyl, trifluoromethoxy-n-propyl,
Difluormethoxymethyl, Difluormethoxyethyl, Difluormethoxy-n-propyl, 2,2- Difluorethoxymethyl, 2,2-Difluorethoxyethyl, 2,2-Difluorethoxy-n-propyl, 2,2,2- Trifluorethoxymethyl, 2,2,2-Trifluorethoxyethyl, 2,2,2-Trifluorethoxy-n-propyl, Pentafluorethoxymethyl, Pentafluorethoxyethyl, Pentafluorethoxy-n-propyl, Methylthiomethyl, Methylthioethyl, Ethylthioethyl, Methylthio-n-propyl, Ethylthio- n-propyl, Trifluormethylthiomethyl, Trifluormethylthioethyl, Trifluormethylthio-n- propyl, COOR23, CONR21R22, Hydroxycarbonyl-(Ci-C5)-alkyl, (C1-C5)-Difluoromethoxymethyl, difluoromethoxyethyl, difluoromethoxy-n-propyl, 2,2-difluoroethoxymethyl, 2,2-difluoroethoxyethyl, 2,2-difluoroethoxy-n-propyl, 2,2,2-trifluoroethoxymethyl, 2,2,2-trifluoroethoxyethyl, 2, 2,2-trifluoroethoxy-n-propyl, pentafluoroethoxymethyl, pentafluoroethoxyethyl, pentafluoroethoxy-n-propyl, methylthiomethyl, methylthioethyl, ethylthioethyl, methylthio-n-propyl, ethylthio-n-propyl, trifluoromethylthiomethyl, trifluoromethylthioethyl, trifluoromethylthio-n-propyl, COOR 23 , CONR 21 R 22 , hydroxycarbonyl- (C 1 -C 5 ) -alkyl, (C 1 -C 5 ) -
Al koxycarbonyl-(Ci -C5)-al kyl , (C2-C6)-Al kenyloxycarbonyl-(Ci -C5)-al kyl , (C2-C6)- Alkinyloxycarbonyl-(Ci-C5)-alkyl, Aryl-(Ci-C5)-alkoxycarbonyl-(Ci-C5)-alkyl, Heteroaryl-(Ci-C5)-alkoxycarbonyl-(Ci-C5)-alkyl, Heterocyclyl-(Ci-C5)- alkoxycarbonyl-(Ci-C5)-alkyl stehen, Al koxycarbonyl- (Ci-C5) -alkyl, (C 2 -C 6) -alkyl kenyloxycarbonyl- (Ci-C5) -alkyl, (C 2 -C 6) - alkynyloxycarbonyl (Ci-C5) - alkyl, aryl- (C 1 -C 5) -alkoxycarbonyl- (C 1 -C 5) -alkyl, Heteroaryl- (C 1 -C 5) -alkoxycarbonyl- (C 1 -C 5) -alkyl, heterocyclyl- (C 1 -C 5) -alkoxycarbonyl- (C 1 -C 5) -alkyl,
R3 und R4 mit dem Stickstoffatom, an das sie gebunden sind, einen vollständig R 3 and R 4 with the nitrogen atom to which they are attached, a complete
gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfalls durch saturated, partially saturated or fully unsaturated, if necessary
Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3-7- gliedrigen Ring bilden, Heteroatoms form interrupted and optionally further substituted 3-7-membered ring,
R1 und X1, wenn X1 für eine Gruppe C-R2 steht, mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig R 1 and X 1 , when X 1 is a group CR 2 , with the atoms to which they are attached, a fully saturated, partially saturated or completely
ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden,  form unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring,
X1 und X2, wenn beide für eine Gruppe C-R2 stehen, mit den Atomen, an die sie X 1 and X 2 , when both represent a group CR 2 , with the atoms to which they belong
gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden,  form a fully saturated, partially saturated or fully unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring,
A1 und A2, wenn beide für eine Gruppe C-R7 stehen, mit den Atomen, an die sie A 1 and A 2 , when both represent a group CR 7 , with the atoms to which they belong
gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden,  form a fully saturated, partially saturated or fully unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring,
A2 und A3, wenn beide für eine Gruppe C-R7 stehen, mit den Atomen, an die sie A 2 and A 3 , when both represent a group CR 7 , with the atoms to which they belong
gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden und  form a fully saturated, partially saturated or fully unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5-7-membered ring and form
A3 und A4, wenn beide für eine Gruppe C-R7 stehen, mit den Atomen, an die sie A 3 and A 4 , when both represent a group CR 7 , with the atoms to which they belong
gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden,  form a fully saturated, partially saturated or fully unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring,
Y für eine Bindung oder für die Gruppierungen Y-1 bis Y-7 Y for a bond or for the groupings Y-1 to Y-7
steht, wobei R8, R9, R10, R1 1, R12, R13, R14, R15, R16, R17, R18 und R19 jeweils die , wherein R 8, R 9, R 10, R 1 1, R 12, R 13, R 14, R 15, R 16, R 17, R 18 and R 19 in each case the
Bedeutung gemäß der nachstehenden Definition haben und wobei der Pfeil für eine Bindung zum 6-gliedrigen Ring mit den Gruppierungen A1, A2, A3, A4 und A5 steht, Have meaning as defined below and wherein the arrow represents a bond to the 6-membered ring with the groupings A 1 , A 2 , A 3 , A 4 and A 5 ,
R8, R9, R10, R1 1, R12, R13, R14, R15, R16, R17, R18 und R19 unabhängig voneinander für Wasserstoff, Fluor, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, iso-Butyl, tert.- Butyl, Ethenyl, 1 -Propenyl, 2-Propenyl, 1 -Methyl-ethenyl, 1 -Butenyl, 2-Butenyl, 3-Butenyl, 1 -Methyl-1 -propenyl, 2-Methyl-1 -propenyl, 1 -Methyl-2-propenyl, 2- Methyl-2-propenyl, Ethinyl, 1 -Propinyl, 2-Propinyl, 1 -Butinyl, 2-Butinyl, 3-Butinyl,R 8, R 9, R 10, R 1 1, R 12, R 13, R 14, R 15, R 16, R 17, R 18 and R 19 independently of one another represent hydrogen, fluorine, methyl, ethyl, n-propyl , iso-propyl, n-butyl, isobutyl, tert-butyl, ethenyl, 1-propenyl, 2-propenyl, 1-methyl-ethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl 1 -propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl,
1 - Methyl-2-propinyl, 1 -Pentinyl, 2-Pentinyl, 3-Pentinyl, 4-Pentinyl, 1 -Methyl-2- butinyl, 1 -Methyl-3-butinyl, 2-Methyl-3-butinyl, 3-Methyl-1 -butinyl, 1 ,1 -Dimethyl-1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3 Methyl-1-butinyl, 1, 1-dimethyl
2- propinyl, 1 -Ethyl-2-propinyl, Trifluormethyl, Pentafluorethyl, 1 ,1 ,2,2- Tetrafluorethyl, Heptafluorpropyl, Nonafluorbutyl, Chlordifluormethyl, 2-propynyl, 1-ethyl-2-propynyl, trifluoromethyl, pentafluoroethyl, 1,1,2,2-tetrafluoroethyl, heptafluoropropyl, nonafluorobutyl, chlorodifluoromethyl,
Bromdifluormethyl, Dichlorfluormethyl, loddifluormethyl, Bromfluormethyl, 1 - Fluorethyl, 2-Fluorethyl, Fluormethyl, Difluormethyl, 1 ,1 -Difluorethyl, 2,2- Difluorethyl, 2,2,2-Trifluorethyl, 3,3,3-Trifluor-n-propyl, Difluor-tert.-butyl, Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Cyclopropylmethyl,  Bromodifluoromethyl, dichlorofluoromethyl, iododifluoromethyl, bromofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, fluoromethyl, difluoromethyl, 1,1-difluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 3,3,3-trifluoro-n- propyl, difluoro-tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl,
Cyclobutylmethyl, Cyclopentylmethyl, Cyclohexylmethyl, gegebenenfalls substituiertes Phenyl, Aryl-(Ci-C6)-alkyl, Heteroaryl, Heteroaryl-(Ci-C6)-alkyl, Heterocyclyl, Heterocyclyl-(Ci-C6)-alkyl, Methoxymethyl, Ethoxymethyl,  Cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, optionally substituted phenyl, aryl- (C 1 -C 6) -alkyl, heteroaryl, heteroaryl- (C 1 -C 6) -alkyl, heterocyclyl, heterocyclyl- (C 1 -C 6) -alkyl, methoxymethyl, ethoxymethyl,
Ethoxyethyl, Methoxyethyl, Methoxy-n-propyl, Ethoxy-n-propyl, Methoxybutyl, Methoxy-iso-Propyl, iso-Propoxymethyl, iso-Propoxyethyl,  Ethoxyethyl, methoxyethyl, methoxy-n-propyl, ethoxy-n-propyl, methoxy-butyl, methoxy-isopropyl, iso-propoxymethyl, iso-propoxyethyl,
Trifluormethoxymethyl, Trifluormethoxyethyl, Trifluormethoxy-n-propyl, Difluormethoxymethyl, Difluormethoxyethyl, Difluormethoxy-n-propyl, 2,2- Difluorethoxymethyl, 2,2-Difluorethoxyethyl, 2,2-Difluorethoxy-n-propyl, 2,2,2- Trifluorethoxymethyl, 2,2,2-Trifluorethoxyethyl, 2,2,2-Trifluorethoxy-n-propyl, Pentafluorethoxymethyl, Pentafluorethoxyethyl, Pentafluorethoxy-n-propyl, Methylthiomethyl, Methylthioethyl, Ethylthioethyl, Methylthio-n-propyl, Ethylthio- n-propyl, Trifluormethylthionnethyl, Trifluormethylthioethyl, Trifluormethylthio-n- propyl, COOR23 stehen, und R6 mit dem Atom, an das sie gebunden sind, einen vollständig gesättigten, oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden, für Wasserstoff, Methyl, Ethyl, n-Propyl, 1 -Methylethyl, n-Butyl, 1 -Methylpropyl, 2-Methylpropyl, 1 ,1 -Dimethylethyl, n-Pentyl, 1 -Methylbutyl, 2-Methylbutyl, 3- Methylbutyl, 1 ,1 -Dimethylpropyl, 1 ,2-Dimethylpropyl, 2,2-Dimethylpropyl, 1 - Ethylpropyl, n-Hexyl, 1 -Methylpentyl, 2-Methylpentyl, 3-Methylpentyl, 4- Methylpentyl, 1 ,1 -Dimethylbutyl, 1 ,2-Dimethylbutyl, 1 ,3-Di-methylbutyl, 2,2- Dimethylbutyl, 2,3-Dimethylbutyl, 3,3-Dimethylbutyl, 1 -Ethylbutyl, 2-Ethylbutyl, 1 ,1 ,2-Trimethylpropyl, 1 ,2,2-Trimethylpropyl, 1 -Ethyl-1 -methylpropyl und 1 - Ethyl-2-methylpropyl, Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl, Cyclohexylmethyl, Cyanomethyl, Cyanoethyl, Cyano-n-propyl, Cyano-n-butyl, Ethenyl, 1 -Propenyl, 2-Propenyl, 1 -Methyl-ethenyl, 1 -Butenyl, 2-Butenyl, 3- Butenyl, 1 -Methyl-1 -propenyl, 2-Methyl-1 -propenyl, 1 -Methyl-2-propenyl, 2- Methyl-2-propenyl, 1 -Pentenyl, 2-Pentenyl, 3-Pentenyl, 4-Pentenyl, 1 -Methyl-1 - butenyl, 2-Methyl-1 -butenyl, 3-Methyl-1 -butenyl, 1 -Methyl-2-butenyl, 2-Methyl-2 butenyl, 3-Methyl-2-butenyl, 1 -Methyl-3-butenyl, 2-Methyl-3-butenyl, 3-Methyl-3 butenyl, 1 ,1 -Dimethyl-2-propenyl, 1 ,2-Dimethyl-1 -propenyl, 1 ,2-Dimethyl-2- propenyl, 1 -Ethyl-1 -propenyl, 1 -Ethyl-2-propenyl, 1 -Hexenyl, 2-Hexenyl, 3- Hexenyl, 4-Hexenyl, 5-Hexenyl, 1 -Methyl-1 -pentenyl, 2-Methyl-1 -pentenyl, 3- Methyl-1 -pentenyl, 4-Methyl-1 -pentenyl, 1 -Methyl-2-pentenyl, 2-Methyl-2- pentenyl, 3-Methyl-2-pentenyl, 4-Methyl-2-pentenyl, 1 -Methyl-3-pentenyl, 2- Methyl-3-pentenyl, 3-Methyl-3-pentenyl, 4-Methyl-3-pentenyl, 1 -Methyl-4- pentenyl, 2-Methyl-4-pentenyl, 3-Methyl-4-pentenyl, 4-Methyl-4-pentenyl, 1 ,1 - Dimethyl-2-butenyl, 1 ,1 -Dimethyl-3-butenyl, 1 ,2-Dimethyl-1 -butenyl, 1 ,2- Dimethyl-2-butenyl, 1 ,2-Dimethyl-3-butenyl, 1 ,3-Dimethyl-1 -butenyl, 1 ,3- Dimethyl-2-butenyl, 1 ,3-Dimethyl-3-butenyl, 2,2-Dimethyl-3-butenyl, 2,3- Dimethyl-1 -butenyl, 2,3-Dimethyl-2-butenyl, 2,3-Dimethyl-3-butenyl, 3,3- Dimethyl-1 -butenyl, 3,3-Dimethyl-2-butenyl, 1 -Ethyl-1 -butenyl, 1 -Ethyl-2-butenylTrifluoromethoxymethyl, trifluoromethoxyethyl, trifluoromethoxy-n-propyl, Difluoromethoxymethyl, difluoromethoxyethyl, difluoromethoxy-n-propyl, 2,2-difluoroethoxymethyl, 2,2-difluoroethoxyethyl, 2,2-difluoroethoxy-n-propyl, 2,2,2-trifluoroethoxymethyl, 2,2,2-trifluoroethoxyethyl, 2, 2,2-trifluoroethoxy-n-propyl, pentafluoroethoxymethyl, pentafluoroethoxyethyl, pentafluoroethoxy-n-propyl, methylthiomethyl, methylthioethyl, ethylthioethyl, methylthio-n-propyl, ethylthio-n-propyl, trifluoromethylthionnethyl, trifluoromethylthioethyl, trifluoromethylthio-n-propyl, COOR 23 and R 6 with the atom to which they are attached form a completely saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring, for hydrogen, methyl, ethyl, n-propyl, 1 -Methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 2 , 2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpent yl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3- Dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2-trimethylpropyl, 1, 2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, Cyanomethyl, cyanoethyl, cyano-n-propyl, cyano-n-butyl, ethenyl, 1-propenyl, 2-propenyl, 1-methyl-ethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1 - propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl 3-butenyl, 3-methyl-3-butenyl, 1, 1-dimethyl-2-propenyl, 1, 2-dimethyl-1-propenyl, 1, 2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-H exenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4- Methyl 3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1, 1-dimethyl-2-butenyl, 1, 1-dimethyl-3-butenyl, 1, 2-dimethyl-1-butenyl, 1, 2 Dimethyl 2-butenyl, 1, 2-dimethyl-3-butenyl, 1, 3-dimethyl-1-butenyl, 1, 3-dimethyl-2-butenyl, 1, 3-dimethyl-3-butenyl, 2.2- Dimethyl 3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3- Dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl
1 - Ethyl-3-butenyl, 2-Ethyl-1 -butenyl, 2-Ethyl-2-butenyl, 2-Ethyl-3-butenyl, 1 ,1 ,2- Trinnethyl-2-propenyl, 1 -Ethyl-1 -methyl-2-propenyl, 1 -Ethyl-2-methyl-1 -propenyl und 1 -Ethyl-2-methyl-2-propenyl, Ethinyl, 1 -Propinyl, 2-Propinyl, 1 -Butinyl, 2- Butinyl, 3-Butinyl, 1 -Methyl-2-propinyl, 1 -Pentinyl, 2-Pentinyl, 3-Pentinyl, 4- Pentinyl, 1 -Methyl-2-butinyl, 1 -Methyl-3-butinyl, 2-Methyl-3-butinyl, 3-Methyl-1 - butinyl, 1 ,1 -Dimethyl-2-propinyl, 1 -Ethyl-2-propinyl, 1 -Hexinyl, 2-Hexinyl, 3- Hexinyl, 4-Hexinyl, 5-Hexinyl, 1 -Methyl-2-pentinyl, 1 -Methyl-3-pentinyl, 1 - Methyl-4-pentinyl, 2-Methyl-3-pentinyl, 2-Methyl-4-pentinyl, 3-Methyl-1 -pentinyl, 3-Methyl-4-pentinyl, 4-Methyl-1 -pentinyl, Methoxy, Ethoxy, n-Propyloxy, iso- Propyloxy, n-Butyloxy, tert.-Butyloxy, (Ci-C6)-Haloalkyl, Cyclopropyl, Cyclobutyl Cyclopentyl, Cyclohexyl, Spiro[2.2]pent-1 -yl, Spiro[2.3]hex-1 -yl, Spiro[2.3]hex-4- yl, 3-Spiro[2.3]hex-5-yl, Spiro[3.3]hept-1 -yl, Spiro[3.3]hept-2-yl, 1 - ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1, 1, 2-trinethyl-2-propenyl, 1-ethyl-1 - methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3- Butinyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl 2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4 pentynyl, 4-methyl-1-pentynyl, methoxy, ethoxy, n-propyloxy, isopropoxy, n-butyloxy, tert-butyloxy, (Ci-C6) -haloalkyl, cyclopropyl, cyclobutyl cyclopentyl, cyclohexyl, spiro [2.2] pent-1-yl, spiro [2.3] hex-1-yl, spiro [2.3] hex-4-yl, 3-spiro [2.3] hex-5-yl, spiro [3.3] hept-1-yl, spiro [ 3.3] hept-2-yl,
Bicyclo[1 .1 .0]butan-1 -yl, Bicyclo[1 .1 .0]butan-2-yl, Bicyclo[2.1 .0]pentan-1 -yl, Bicyclo[1 .1 .1 ]pentan-1 -yl, Bicyclo[2.1 .0]pentan-2-yl, Bicyclo[2.1 .0]pentan-5-yl, Bicyclo[2.1 .1 ]hexyl, Bicyclo[2.2.1 ]hept-2-yl, Bicyclo[2.2.2]octan-2-yl,  Bicyclo [1-1.0] butan-1-yl, bicyclo [1-1.0] butan-2-yl, bicyclo [2.1.0] pentan-1-yl, bicyclo [1,11,1] pentane 1 -yl, bicyclo [2.1.0] pentan-2-yl, bicyclo [2.1.0] pentan-5-yl, bicyclo [2.1.1] hexyl, bicyclo [2.2.1] hept-2-yl, bicyclo 2.2.2] octan-2-yl,
Bicyclo[3.2.1 ]octan-2-yl, Bicyclo[3.2.2]nonan-2-yl, Adamantan-1 -yl, Adamantan-Bicyclo [3.2.1] octan-2-yl, bicyclo [3.2.2] nonan-2-yl, adamantan-1-yl, adamantane
2- yl, 1 -Methylcyclopropyl, 2-Methylcyclopropyl, 2,2-Dimethylcyclopropyl, 2,3- Dimethylcyclopropyl, 1 ,1 '-Bi(cyclopropyl)-1 -yl, 1 ,1 '-Bi(cyclopropyl)-2-yl, 2'- Methyl-1 ,1 '-bi(cyclopropyl)-2-yl, gegebenenfalls substituiertes Phenyl, 2-yl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, 2,3-dimethylcyclopropyl, 1,1'-bis (cyclopropyl) -1-yl, 1,1'-bis (cyclopropyl) -2- yl, 2'-methyl-1, 1'-bi (cyclopropyl) -2-yl, optionally substituted phenyl,
Heteroaryl, Heterocyclyl, (Ci-C6)-Alkylcarbonyl, Aryl-(Ci-C5)-Alkylcarbonyl, (C3-C6)-Cycloalkylcarbonyl, Arylcarbonyl, Heteroarylcarbonyl, (C1-C5)- Alkoxycarbonyl, (C2-C6)-Alkenyloxycarbonyl, Aryl-(Ci-C5)-alkoxycarbonyl, Heteroaryl-(Ci-Cs)-al koxycarbonyl , (C3-C6)-Cycloal kyl-(Ci-Cs)-al koxycarbonyl , (Ci-C5)-Alkylsulfonyl, (Ci-CsJ-Haloalkylsulfonyl, Arylsulfonyl, Heteroarylsulfonyl, (C3-C6)-Cycloalkylsulfonyl, (Ci-Cs)-Al kylsulfinyl, Arylsulfinyl, Heteroarylsulfinyl, (C3-C6)-Cycloalkylsulfinyl steht, für 0, 1 oder 2 steht R22 gleich oder verschieden sind und unabhängig voneinander für Heteroaryl, heterocyclyl, (C 1 -C 6) -alkylcarbonyl, aryl- (C 1 -C 5) -alkylcarbonyl, (C 3 -C 6) -cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, (C 1 -C 5) -alkoxycarbonyl, (C 2 -C 6) -alkenyloxycarbonyl, Aryl- (C 1 -C 5) -alkoxycarbonyl, heteroaryl- (C 1 -C 5) -alkenoxycarbonyl, (C 3 -C 6) -cycloalkyl (C 1 -C 5) -alkenoxycarbonyl, (C 1 -C 5) -alkylsulfonyl, CsJ-haloalkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, (C3-C6) -cycloalkylsulfonyl, (Ci-Cs) -alkylsulfinyl, arylsulfinyl, heteroarylsulfinyl, (C3-C6) -cycloalkylsulfinyl, is 0, 1 or 2 R 22 are the same or different and are independently of each other
Wasserstoff, Methyl, Ethyl, n-Propyl, 1 -Methylethyl, n-Butyl, 1 -Methylpropyl, 2- Methylpropyl, 1 ,1 -Dimethylethyl, n-Pentyl, 1 -Methylbutyl, 2-Methylbutyl, 3- Methylbutyl, 1 ,1 -Dimethylpropyl, 1 ,2-Dimethylpropyl, 2,2-Dimethylpropyl, 1 - Ethylpropyl, n-Hexyl, 1 -Methylpentyl, 2-Methylpentyl, 3-Methylpentyl, 4- Methylpentyl, 1 ,1 -Dimethylbutyl, 1 ,2-Dimethylbutyl, 1 ,3-Di-methylbutyl, 2,2- Dimethylbutyl, 2,3-Dimethylbutyl, 3,3-Dimethylbutyl, 1 -Ethylbutyl, 2-Ethylbutyl, 1 ,1 ,2-Thmethylpropyl, 1 ,2,2-Thmethylpropyl, 1 -Ethyl-1 -methylpropyl und 1 - Ethyl-2-methylpropyl, Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl, Cyclohexylmethyl, Cyanomethyl, Cyanoethyl, Cyano-n-propyl, Cyano-n-butyl, Ethenyl, 1 -Propenyl, 2-Propenyl, 1 -Methyl-ethenyl, 1 -Butenyl, 2-Butenyl, 3- Butenyl, 1 -Methyl-1 -propenyl, 2-Methyl-1 -propenyl, 1 -Methyl-2-propenyl, 2- Methyl-2-propenyl, 1 -Pentenyl, 2-Pentenyl, 3-Pentenyl, 4-Pentenyl, 1 -Methyl-1 - butenyl, 2-Methyl-1 -butenyl, 3-Methyl-1 -butenyl, 1 -Methyl-2-butenyl, 2-Methyl-2- butenyl, 3-Methyl-2-butenyl, 1 -Methyl-3-butenyl, 2-Methyl-3-butenyl, 3-Methyl-3- butenyl, 1 ,1 -Dimethyl-2-propenyl, 1 ,2-Dimethyl-1 -propenyl, 1 ,2-Dimethyl-2- propenyl, 1 -Ethyl-1 -propenyl, 1 -Ethyl-2-propenyl, 1 -Hexenyl, 2-Hexenyl, 3- Hexenyl, 4-Hexenyl, 5-Hexenyl, 1 -Methyl-1 -pentenyl, 2-Methyl-1 -pentenyl, 3- Methyl-1 -pentenyl, 4-Methyl-1 -pentenyl, 1 -Methyl-2-pentenyl, 2-Methyl-2- pentenyl, 3-Methyl-2-pentenyl, 4-Methyl-2-pentenyl, 1 -Methyl-3-pentenyl, 2- Methyl-3-pentenyl, 3-Methyl-3-pentenyl, 4-Methyl-3-pentenyl, 1 -Methyl-4- pentenyl, 2-Methyl-4-pentenyl, 3-Methyl-4-pentenyl, 4-Methyl-4-pentenyl, 1 ,1 - Dimethyl-2-butenyl, 1 ,1 -Dimethyl-3-butenyl, 1 ,2-Dimethyl-1 -butenyl, 1 ,2- Dimethyl-2-butenyl, 1 ,2-Dimethyl-3-butenyl, 1 ,3-Dimethyl-1 -butenyl, 1 ,3- Dimethyl-2-butenyl, 1 ,3-Dimethyl-3-butenyl, 2,2-Dimethyl-3-butenyl, 2,3- Dimethyl-1 -butenyl, 2,3-Dimethyl-2-butenyl, 2,3-Dimethyl-3-butenyl, 3,3- Dimethyl-1 -butenyl, 3,3-Dimethyl-2-butenyl, 1 -Ethyl-1 -butenyl, 1 -Ethyl-2-butenyl, 1 -Ethyl-3-butenyl, 2-Ethyl-1 -butenyl, 2-Ethyl-2-butenyl, 2-Ethyl-3-butenyl, 1 ,1 ,2- Trimethyl-2-propenyl, 1 -Ethyl-1 -methyl-2-propenyl, 1 -Ethyl-2-methyl-1 -propenyl und 1 -Ethyl-2-methyl-2-propenyl, Ethinyl, 1 -Propinyl, 2-Propinyl, 1 -Butinyl, 2- Butinyl, 3-Butinyl, 1 -Methyl-2-propinyl, 1 -Pentinyl, 2-Pentinyl, 3-Pentinyl, 4- Pentinyl, 1 -Methyl-2-butinyl, 1 -Methyl-3-butinyl, 2-Methyl-3-butinyl, 3-Methyl-1 - butinyl, 1 ,1 -Dimethyl-2-propinyl, 1 -Ethyl-2-propinyl, 1 -Hexinyl, 2-Hexinyl, 3- Hexinyl, 4-Hexinyl, 5-Hexinyl, 1 -Methyl-2-pentinyl, 1 -Methyl-3-pentinyl, 1 - Methyl-4-pentinyl, 2-Methyl-3-pentinyl, 2-Methyl-4-pentinyl, 3-Methyl-1 -pentinyl, 3-Methyl-4-pentinyl, 4-Methyl-1 -pentinyl, 4-Methyl-2-pentinyl, 1 ,1 -Dimethyl-2- butinyl, 1 ,1 -Dimethyl-3-butinyl, 1 ,2-Dimethyl-3-butinyl, 2,2-Dimethyl-3-butinyl, 3,3-Dimethyl-1 -butinyl, 1 -Ethyl-2-butinyl, 1 -Ethyl-3-butinyl, 2-Ethyl-3-butinyl, 1 - Ethyl-1 -methyl-2-propinyl, (Ci-C6)-Haloalkyl, (C2-C6)-Haloalkenyl, (C2-C6)- Haloalkinyl, Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Spiro[2.2]pent-1 - yl, Spiro[2.3]hex-1 -yl, Spiro[2.3]hex-4-yl, 3-Spiro[2.3]hex-5-yl, Spiro[3.3]hept-1 - yl, Spiro[3.3]hept-2-yl, Bicyclo[1 .1 .0]butan-1 -yl, Bicyclo[1 .1 .0]butan-2-yl, Is hydrogen, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2 Dimethylbutyl, 1, 3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2-thmethylpropyl, 1, 2,2- Thmethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyanomethyl, cyanoethyl, cyano-n-propyl, cyano-n-butyl, ethenyl, 1 -propenyl, 2- Propenyl, 1-methyl-ethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2 propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl , 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1 , 1-dimethyl-2-propenyl, 1, 2-dimethyl-1-propenyl, 1, 2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2 -Hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl 2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3 pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1, 1-dimethyl-2 -butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1 -butenyl, 1,3-dimethyl-2-butenyl, 1, 3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2 -butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2 -butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl , 1, 1, 2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl, ethynyl , 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2 -butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2 Hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1 - Methyl 4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl 2-pentynyl, 1, 1-dimethyl-2-butynyl, 1, 1-dimethyl-3-butynyl, 1, 2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl 1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl, (C 1 -C 6 ) -haloalkyl, ( C 2 -C 6 ) -haloalkenyl, (C 2 -C 6 ) -haloalkynyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, spiro [2.2] pent-1-yl, spiro [2.3] hex-1-yl, spiro [2.3] hex-4-yl, 3-spiro [2.3] hex-5-yl, spiro [3.3] hept-1-yl, spiro [3.3] hept-2-yl, bicyclo [1 .1 .0] butane-1 - yl, bicyclo [1 .1 .0] butan-2-yl,
Bicyclo[2.1 .0]pentan-1 -yl, Bicyclo[1 .1 .1 ]pentan-1 -yl, Bicyclo[2.1 .0]pentan-2-yl, Bicyclo[2.1 .0]pentan-5-yl, Bicyclo[2.1 .1 ]hexyl, Bicyclo[2.2.1]hept-2-yl, Bicyclo [2.1.0] pentan-1-yl, bicyclo [1,11,1] pentan-1-yl, bicyclo [2.1.0] pentan-2-yl, bicyclo [2.1.0] pentan-5-yl, Bicyclo [2.1.1] hexyl, bicyclo [2.2.1] hept-2-yl,
Bicyclo[2.2.2]octan-2-yl, Bicyclo[3.2.1 ]octan-2-yl, Bicyclo[3.2.2]nonan-2-yl, Adamantan-1 -yl, Adamantan-2-yl, 1 -Methylcyclopropyl, 2-Methylcyclopropyl, 2,2-Dimethylcyclopropyl, 2,3-Dimethylcyclopropyl, 1 ,1 '-Bi(cyclopropyl)-1 -yl, 1 ,1 '- Bi(cyclopropyl)-2-yl, 2'-Methyl-1 ,1 '-bi(cyclopropyl)-2-yl, 1 -Cyanocyclopropyl, 2- Cyanocyclopropyl, 1 -Methylcyclobutyl, 2-Methylcyclobutyl, 3-Methylcyclobutyl, 1 -Cyanocyclobutyl, 2-Cyanocyclobutyl, 3-Cyanocyclobutyl, 3-Methoxycyclobutyl, 1 -Allylcyclopropyl, 1 -Vinylcyclobutyl, 1 -Vinylcyclopropyl, 1 -Ethylcyclopropyl, 1 - Methylcyclohexyl, 2-Methylcyclohexyl, 3-Methylcyclohexyl, 1 - Methoxycyclohexyl, 2-Methoxycyclohexyl, 3-Methoxycyclohexyl, 4- Methoxycyclohexyl, Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentyl methyl, Cyclohexylmethyl, (C3-C6)-Halocycloalkyl, (C4-C6)-Cycloalkenyl, (C4-C6)- Halocycloalkenyl, Methoxymethyl, Ethoxymethyl, Ethoxyethyl, Methoxyethyl, Methoxy-n-propyl, Ethoxy-n-propyl, Methoxybutyl, Methoxy-iso-Propyl, iso- Propoxymethyl, iso-Propoxyethyl, Thfluormethoxymethyl, Thfluormethoxyethyl, Thfluormethoxy-n-propyl, Difluormethoxymethyl, Difluormethoxyethyl, Bicyclo [2.2.2] octan-2-yl, bicyclo [3.2.1] octan-2-yl, bicyclo [3.2.2] nonan-2-yl, adamantan-1-yl, adamantan-2-yl, 1 - Methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, 2,3-dimethylcyclopropyl, 1,1'-bis (cyclopropyl) -1-yl, 1,1'-bi (cyclopropyl) -2-yl, 2'-methyl -1, 1'-bi (cyclopropyl) -2-yl, 1-cyanocyclopropyl, 2-cyanocyclopropyl, 1-methylcyclobutyl, 2-methylcyclobutyl, 3-methylcyclobutyl, 1-cyanocyclobutyl, 2-cyanocyclobutyl, 3-cyanocyclobutyl, 3-methoxycyclobutyl , 1-allylcyclopropyl, 1-vinylcyclobutyl, 1-vinylcyclopropyl, 1-ethylcyclopropyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 1-methoxycyclohexyl, 2-methoxycyclohexyl, 3-methoxycyclohexyl, 4-methoxycyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentyl methyl, cyclohexylmethyl, (C 3 -C 6) -halocycloalkyl, (C 4 -C 6) -cycloalkenyl, (C 4 -C 6) -halocycloalkenyl, methoxymethyl, ethoxymethyl, ethoxyethyl, methoxyethyl, methoxy-n-propyl, ethoxy-n-propyl, Methoxybutyl, methoxy-iso-propyl, iso- Propoxymethyl, iso -propoxyethyl, thfluoromethoxymethyl, thfluoromethoxyethyl, thfluoromethoxy-n-propyl, difluoromethoxymethyl, difluoromethoxyethyl,
Difluormethoxy-n-propyl, 2,2-Difluorethoxymethyl, 2,2-Difluorethoxyethyl, 2,2- Difluorethoxy-n-propyl, 2,2,2-Thfluorethoxynnethyl, 2,2,2-Thfluorethoxyethyl, 2,2,2-Thfluorethoxy-n-propyl, Pentafluorethoxymethyl, Pentafluorethoxyethyl, Pentafluorethoxy-n-propyl, Methylthiomethyl, Methylthioethyl, Ethylthioethyl, Methylthio-n-propyl, Ethylthio-n-propyl, Trifluormethylthiomethyl, Difluoromethoxy-n-propyl, 2,2-difluoroethoxymethyl, 2,2-difluoroethoxyethyl, 2,2-difluoroethoxy-n-propyl, 2,2,2-thfluoroethoxynethyl, 2,2,2-thfluoroethoxyethyl, 2,2,2- Thfluoroethoxy-n-propyl, pentafluoroethoxymethyl, pentafluoroethoxyethyl, pentafluoroethoxy-n-propyl, methylthiomethyl, methylthioethyl, ethylthioethyl, methylthio-n-propyl, ethylthio-n-propyl, trifluoromethylthiomethyl,
Thfluormethylthioethyl, Trifluormethylthio-n-propyl, gegebenenfalls substituiertes Phenyl, Aryl-(Ci-C5)-alkyl, Heteroaryl, Heteroaryl-(Ci-C5)-alkyl, (C -C6)- Cycloalkenyl-(Ci-C5)-alkyl, COR23, SO2R24, -(Ci-C6)-Alkyl-HNO2S-, (C3-C6)- Cycloalkyl-HNO2S-, Heterocyclyl, (Ci-C5)-Alkoxycarbonyl-(Ci-C5)-alkyl, (C1-C5)- Alkoxycarbonyl, Aryl-(Ci-C5)-Alkoxycarbonyl-(Ci-C5)-alkyl, Aryl-(Ci-Cs)- Alkoxycarbonyl, Heteroaryl-(Ci-C5)-Alkoxycarbonyl, (C2-C6)-Alkenyloxycarbonyl (C2-C6)-Alkinyloxycarbonyl, Heterocyclyl-(Ci-C5)-alkyl stehen für Wasserstoff, Methyl, Ethyl, n-Propyl, 1 -Methylethyl, n-Butyl, 1 -Methylpropyl, 2-Methylpropyl, 1 ,1 -Dimethylethyl, n-Pentyl, 1 -Methylbutyl, 2-Methylbutyl, 3- Methylbutyl, 1 ,1 -Dimethylpropyl, 1 ,2-Dimethylpropyl, 2,2-Dimethylpropyl, 1 - Ethylpropyl, n-Hexyl, 1 -Methylpentyl, 2-Methylpentyl, 3-Methylpentyl, 4- Methylpentyl, 1 ,1 -Dimethylbutyl, 1 ,2-Dimethylbutyl, 1 ,3-Di-methylbutyl, 2,2- Dimethylbutyl, 2,3-Dimethylbutyl, 3,3-Dimethylbutyl, 1 -Ethylbutyl, 2-Ethylbutyl, 1 ,1 ,2-Thmethylpropyl, 1 ,2,2-Thmethylpropyl, 1 -Ethyl-1 -methylpropyl und 1 - Ethyl-2-methylpropyl, Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl, Cyclohexylmethyl, Cyanomethyl, Cyanoethyl, Cyano-n-propyl, Cyano-n-butyl, Ethenyl, 1 -Propenyl, 2-Propenyl, 1 -Methyl-ethenyl, 1 -Butenyl, 2-Butenyl, 3- Butenyl, 1 -Methyl-1 -propenyl, 2-Methyl-1 -propenyl, 1 -Methyl-2-propenyl, 2- Methyl-2-propenyl, 1 -Pentenyl, 2-Pentenyl, 3-Pentenyl, 4-Pentenyl, 1 -Methyl-1 - butenyl, 2-Methyl-1 -butenyl, 3-Methyl-1 -butenyl, 1 -Methyl-2-butenyl, 2-Methyl-2 butenyl, 3-Methyl-2-butenyl, 1 -Methyl-3-butenyl, 2-Methyl-3-butenyl, 3-Methyl-3 butenyl, 1 ,1 -Dimethyl-2-propenyl, 1 ,2-Dimethyl-1 -propenyl, 1 ,2-Dimethyl-2- propenyl, 1 -Ethyl-1 -propenyl, 1 -Ethyl-2-propenyl, 1 -Hexenyl, 2-Hexenyl, 3- Hexenyl, 4-Hexenyl, 5-Hexenyl, 1 -Methyl-1 -pentenyl, 2-Methyl-1 -pentenyl, 3- Methyl-1 -pentenyl, 4-Methyl-1 -pentenyl, 1 -Methyl-2-pentenyl, 2-Methyl-2- pentenyl, 3-Methyl-2-pentenyl, 4-Methyl-2-pentenyl, 1 -Methyl-3-pentenyl, 2- Methyl-3-pentenyl, 3-Methyl-3-pentenyl, 4-Methyl-3-pentenyl, 1 -Methyl-4- pentenyl, 2-Methyl-4-pentenyl, 3-Methyl-4-pentenyl, 4-Methyl-4-pentenyl, 1 ,1 - Dimethyl-2-butenyl, 1 ,1 -Dimethyl-3-butenyl, 1 ,2-Dimethyl-1 -butenyl, 1 ,2- Dimethyl-2-butenyl, 1 ,2-Dimethyl-3-butenyl, 1 ,3-Dimethyl-1 -butenyl, 1 ,3- Dimethyl-2-butenyl, 1 ,3-Dimethyl-3-butenyl, 2,2-Dimethyl-3-butenyl, 2,3- Dimethyl-1 -butenyl, 2,3-Dimethyl-2-butenyl, 2,3-Dimethyl-3-butenyl, 3,3- Dimethyl-1 -butenyl, 3,3-Dimethyl-2-butenyl, 1 -Ethyl-1 -butenyl, 1 -Ethyl-2-butenyl 1 -Ethyl-3-butenyl, 2-Ethyl-1 -butenyl, 2-Ethyl-2-butenyl, 2-Ethyl-3-butenyl, 1 ,1 ,2- Trimethyl-2-propenyl, 1 -Ethyl-1 -methyl-2-propenyl, 1 -Ethyl-2-methyl-1 -propenyl und 1 -Ethyl-2-methyl-2-propenyl, Ethinyl, 1 -Propinyl, 2-Propinyl, 1 -Butinyl, 2- Butinyl, 3-Butinyl, 1 -Methyl-2-propinyl, 1 -Pentinyl, 2-Pentinyl, 3-Pentinyl, 4- Pentinyl, 1 -Methyl-2-butinyl, 1 -Methyl-3-butinyl, 2-Methyl-3-butinyl, 3-Methyl-1 - butinyl, 1 ,1 -Dimethyl-2-propinyl, 1 -Ethyl-2-propinyl, 1 -Hexinyl, 2-Hexinyl, 3- Hexinyl, 4-Hexinyl, 5-Hexinyl, 1 -Methyl-2-pentinyl, 1 -Methyl-3-pentinyl, 1 - Methyl-4-pentinyl, 2-Methyl-3-pentinyl, 2-Methyl-4-pentinyl, 3-Methyl-1 -pentinyl, 3-Methyl-4-pentinyl, 4-Methyl-1 -pentinyl, 4-Methyl-2-pentinyl, 1 ,1 -Dimethyl-2- butinyl, 1 ,1 -Dimethyl-3-butinyl, 1 ,2-Dimethyl-3-butinyl, 2,2-Dimethyl-3-butinyl, 3,3-Dimethyl-1 -butinyl, 1 -Ethyl-2-butinyl, 1 -Ethyl-3-butinyl, 2-Ethyl-3-butinyl, 1 - Ethyl-1 -methyl-2-propinyl, Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, , Spiro[2.2]pent-1 -yl, Spiro[2.3]hex-1 -yl, Spiro[2.3]hex-4-yl, 3-Spiro[2.3]hex-5-yl, Spiro[3.3]hept-1 -yl, Spiro[3.3]hept-2-yl, Bicyclo[1 .1 .0]butan-1 -yl, Thfluoromethylthioethyl, trifluoromethylthio-n-propyl, optionally substituted phenyl, aryl- (Ci-C 5 ) -alkyl, heteroaryl, heteroaryl (Ci-C 5 ) -alkyl, (C -C 6 ) - cycloalkenyl- (Ci-C 5 ) alkyl, COR 23, SO 2 R 24, - (Ci-C6) alkyl-HNO 2 S, (C 3 -C 6) - cycloalkyl-HNO 2 S, heterocyclyl, (Ci-C5) - Alkoxycarbonyl- (C 1 -C 5 ) -alkyl, (C 1 -C 5 ) - Alkoxycarbonyl, aryl- (C 1 -C 5 ) -alkoxycarbonyl- (C 1 -C 5 ) -alkyl, aryl- (C 1 -C 8) -alkoxycarbonyl, heteroaryl- (C 1 -C 5 ) -alkoxycarbonyl, (C 2 -C 6) -alkenyloxycarbonyl (C2 -C 6) -Alkynyloxycarbonyl, heterocyclyl- (C 1 -C 5) -alkyl are hydrogen, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, n -Pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3 Methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2 Ethyl butyl, 1, 1, 2-thmethylpropyl, 1, 2,2-thmethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyanomethyl, cyanoethyl, cyano-n -propyl, cyano-n-butyl, ethenyl, 1-propenyl, 2-propenyl, 1-methyl-ethenyl, 1-butenyl, 2-but enyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl , 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, 1-dimethyl-2-propenyl, 1, 2-dimethyl-1-propenyl, 1, 2-dimethyl 2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2- Methyl 1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl 2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4 pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1, 1-dimethyl-3-butenyl, 1, 2-dimethyl-1-butenyl, 1, 2-Dimethyl-2-butenyl, 1, 2-dimethyl-3-butenyl , 1, 3-Dimethyl-1-butenyl, 1, 3-dimethyl-2-butenyl, 1, 3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl , 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1 Ethyl-2-butenyl 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1, 1, 2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4- Pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, 1-ethyl-2-yl propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl 3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1, 1-dimethyl 2-butynyl, 1, 1-dimethyl-3-butynyl, 1, 2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2- butinyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, spiro [2.2] pent-1-yl, spiro [2.3] hex-1-yl, spiro [2.3] hex-4-yl, 3-spiro [2.3] hex-5-yl, spiro [3.3] hept-1-yl, spiro [3.3] hept-2-yl , Bicyclo [1 .1 .O] butan-1-yl,
Bicyclo[1 .1 .0]butan-2-yl, Bicyclo[2.1 .0]pentan-1 -yl, Bicyclo[1 .1 .1 ]pentan-1 -yl, Bicyclo[2.1 .0]pentan-2-yl, Bicyclo[2.1 .0]pentan-5-yl, Bicyclo[2.1 .1]hexyl, Bicyclo [1-1, 0] butan-2-yl, bicyclo [2.1.0] pentan-1-yl, bicyclo [1,11,1] pentan-1-yl, bicyclo [2.1.0] pentan-2-yl yl, bicyclo [2.1.0] pentan-5-yl, bicyclo [2.1.1] hexyl,
Bicyclo[2.2.1 ]hept-2-yl, Bicyclo[2.2.2]octan-2-yl, Bicyclo[3.2.1 ]octan-2-yl, Bicyclo[3.2.2]nonan-2-yl, Adamantan-1 -yl, Adamantan-2-yl, 1 - Methylcyclopropyl, 2-Methylcyclopropyl, 2,2-Dimethylcyclopropyl, 2,3- Dimethylcyclopropyl, 1 ,1 '-Bi(cyclopropyl)-1 -yl, 1 ,1 '-Bi(cyclopropyl)-2-yl, 2'- Methyl-1 ,1 '-bi(cyclopropyl)-2-yl, 2-Cyanocyclopropyl, 1 -Methylcyclobutyl, 2- Methylcyclobutyl, 3-Methylcyclobutyl, 2-Cyanocyclobutyl, 3-Cyanocyclobutyl, 3- Methoxycyclobutyl, 1 -AI lyl cyclopropyl, 1 -Ethylcyclopropyl, 1 -Methylcyclohexyl, 2-Methylcyclohexyl, 3-Methylcyclohexyl, 2-Methoxycyclohexyl, 3- Methoxycyclohexyl, 4-Methoxycyclohexyl, Cyclopropylnnethyl, Cyclobutylnnethyl, Cyclopentyl methyl, Cyclohexylmethyl, Trifluormethyl, Pentafluorethyl, 1 ,1 ,2,2- Tetrafluorethyl, Heptafluorpropyl, Nonafluorbutyl, Chlordifluormethyl, Bicyclo [2.2.1] hept-2-yl, bicyclo [2.2.2] octan-2-yl, bicyclo [3.2.1] octan-2-yl, bicyclo [3.2.2] nonan-2-yl, adamantane 1 -yl, adamantan-2-yl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, 2,3-dimethylcyclopropyl, 1,1'-bis (cyclopropyl) -1-yl, 1,1 '-Bi (cyclopropyl) -2-yl, 2'-methyl-1, 1 '-bi (cyclopropyl) -2-yl, 2-cyanocyclopropyl, 1-methylcyclobutyl, 2-methylcyclobutyl, 3-methylcyclobutyl, 2-cyanocyclobutyl, 3-cyanocyclobutyl , 3-methoxycyclobutyl, 1-allylcyclopropyl, 1-ethylcyclopropyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 2-methoxycyclohexyl, 3-methoxycyclohexyl, 4-methoxycyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, trifluoromethyl, Pentafluoroethyl, 1,1,2,2-tetrafluoroethyl, heptafluoropropyl, nonafluorobutyl, chlorodifluoromethyl,
Bromdifluormethyl, Dichlorfluormethyl, loddifluormethyl, Bromfluormethyl, 1 - Fluorethyl, 2-Fluorethyl, Fluormethyl, Difluormethyl, 2,2-Difluorethyl, 2,2,2- Trifluorethyl, 3,3-Difluor-n-propyl, 3,3,3-Trifluor-n-propyl, 4,4-Difluor-n-butyl, 4,4,4-Trifluor-n-butyl, (C2-C6)-Haloalkenyl, (C2-C6)-Haloalkinyl, (C3-C6)- Halocycloalkyl, (C4-C6)-Cycloalkenyl, (C4-C6)-Halocycloalkenyl, Methoxymethyl, Ethoxymethyl, Ethoxyethyl, Methoxyethyl, Methoxy-n-propyl, Ethoxy-n-propyl, Methoxybutyl, Methoxy-iso-Propyl, iso-Propoxymethyl, iso-Propoxyethyl, gegebenenfalls substituiertes Phenyl, Aryl-(Ci-C6)-alkyl, Heteroaryl, Heteroaryl- (Ci -C6)-al kyl , (C -C6)-Cycloal kenyl-(Ci -C6)-al kyl , (Ci -C6)-Al koxycarbonyl- (Ci -C6)-al kyl , (C2-C6)-Al kenyloxycarbonyl-(Ci -C6)-al kyl , Aryl-(Ci -C6)- AI koxycarbonyl-(Ci -C6)-al kyl , Hydroxycarbonyl-(Ci -C6)-al kyl , Heterocyclyl , Heterocyclyl-(Ci-C6)-alkyl steht und für Wasserstoff, Methyl, Ethyl, n-Propyl, 1 -Methylethyl, n-Butyl, 1 -Methylpropyl, 2-Methylpropyl, 1 ,1 -Dimethylethyl, n-Pentyl, 1 -Methylbutyl, 2-Methylbutyl, 3- Methylbutyl, 1 ,1 -Dimethylpropyl, 1 ,2-Dimethylpropyl, 2,2-Dimethylpropyl, 1 - Ethylpropyl, n-Hexyl, 1 -Methylpentyl, 2-Methylpentyl, 3-Methylpentyl, 4- Methylpentyl, 1 ,1 -Dimethylbutyl, 1 ,2-Dimethylbutyl, 1 ,3-Di-methylbutyl, 2,2- Dimethylbutyl, 2,3-Dimethylbutyl, 3,3-Dimethylbutyl, 1 -Ethylbutyl, 2-Ethylbutyl, 1 ,1 ,2-Trimethylpropyl, 1 ,2,2-Trimethylpropyl, 1 -Ethyl-1 -methylpropyl und 1 - Ethyl-2-methylpropyl, Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl, Cyclohexylmethyl, Cyanomethyl, Cyanoethyl, Cyano-n-propyl, Cyano-n-butyl, Ethenyl, 1 -Propenyl, 2-Propenyl, 1 -Methyl-ethenyl, 1 -Butenyl, 2-Butenyl, 3- Butenyl, 1 -Methyl-1 -propenyl, 2-Methyl-1 -propenyl, 1 -Methyl-2-propenyl, 2- Methyl-2-propenyl, 1 -Pentenyl, 2-Pentenyl, 3-Pentenyl, 4-Pentenyl, 1 -Methyl-1 - butenyl, 2-Methyl-1 -butenyl, 3-Methyl-1 -butenyl, 1 -Methyl-2-butenyl, 2-Methyl-2- butenyl, 3-Methyl-2-butenyl, 1 -Methyl-3-butenyl, 2-Methyl-3-butenyl, 3-Methyl-3- butenyl, 1 ,1 -Dimethyl-2-propenyl, 1 ,2-Dimethyl-1 -propenyl, 1 ,2-Dimethyl-2- propenyl, 1 -Ethyl-1 -propenyl, 1 -Ethyl-2-propenyl, 1 -Hexenyl, 2-Hexenyl, 3- Hexenyl, 4-Hexenyl, 5-Hexenyl, 1 -Methyl-1 -pentenyl, 2-Methyl-1 -pentenyl, 3- Methyl-1 -pentenyl, 4-Methyl-1 -pentenyl, 1 -Methyl-2-pentenyl, 2-Methyl-2- pentenyl, 3-Methyl-2-pentenyl, 4-Methyl-2-pentenyl, 1 -Methyl-3-pentenyl, 2- Methyl-3-pentenyl, 3-Methyl-3-pentenyl, 4-Methyl-3-pentenyl, 1 -Methyl-4- pentenyl, 2-Methyl-4-pentenyl, 3-Methyl-4-pentenyl, 4-Methyl-4-pentenyl, 1 ,1 - Dimethyl-2-butenyl, 1 ,1 -Dimethyl-3-butenyl, 1 ,2-Dimethyl-1 -butenyl, 1 ,2- Dimethyl-2-butenyl, 1 ,2-Dimethyl-3-butenyl, 1 ,3-Dimethyl-1 -butenyl, 1 ,3- Dimethyl-2-butenyl, 1 ,3-Dimethyl-3-butenyl, 2,2-Dimethyl-3-butenyl, 2,3- Dimethyl-1 -butenyl, 2,3-Dimethyl-2-butenyl, 2,3-Dimethyl-3-butenyl, 3,3- Dimethyl-1 -butenyl, 3,3-Dimethyl-2-butenyl, 1 -Ethyl-1 -butenyl, 1 -Ethyl-2-butenyl, 1 -Ethyl-3-butenyl, 2-Ethyl-1 -butenyl, 2-Ethyl-2-butenyl, 2-Ethyl-3-butenyl, 1 ,1 ,2- Thmethyl-2-propenyl, 1 -Ethyl-1 -methyl-2-propenyl, 1 -Ethyl-2-methyl-1 -propenyl und 1 -Ethyl-2-methyl-2-propenyl, Ethinyl, 1 -Propinyl, 2-Propinyl, 1 -Butinyl, 2- Butinyl, 3-Butinyl, 1 -Methyl-2-propinyl, 1 -Pentinyl, 2-Pentinyl, 3-Pentinyl, 4- Pentinyl, 1 -Methyl-2-butinyl, 1 -Methyl-3-butinyl, 2-Methyl-3-butinyl, 3-Methyl-1 - butinyl, 1 ,1 -Dimethyl-2-propinyl, 1 -Ethyl-2-propinyl, 1 -Hexinyl, 2-Hexinyl, 3- Hexinyl, 4-Hexinyl, 5-Hexinyl, 1 -Methyl-2-pentinyl, 1 -Methyl-3-pentinyl, 1 - Methyl-4-pentinyl, 2-Methyl-3-pentinyl, 2-Methyl-4-pentinyl, 3-Methyl-1 -pentinyl, 3-Methyl-4-pentinyl, 4-Methyl-1 -pentinyl, 4-Methyl-2-pentinyl, 1 ,1 -Dimethyl-2- butinyl, 1 ,1 -Dimethyl-3-butinyl, 1 ,2-Dimethyl-3-butinyl, 2,2-Dimethyl-3-butinyl, 3,3-Dimethyl-1 -butinyl, 1 -Ethyl-2-butinyl, 1 -Ethyl-3-butinyl, 2-Ethyl-3-butinyl, 1 - Ethyl-1 -methyl-2-propinyl, Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, , Spiro[2.2]pent-1 -yl, Spiro[2.3]hex-1 -yl, Spiro[2.3]hex-4-yl, 3-Spiro[2.3]hex-5-yl, Spiro[3.3]hept-1 -yl, Spiro[3.3]hept-2-yl, Bicyclo[1 .1 .0]butan-1 -yl, Bromodifluoromethyl, dichlorofluoromethyl, iododifluoromethyl, bromofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, fluoromethyl, difluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 3,3-difluoro-n-propyl, 3,3,3- trifluoro-n-propyl, 4,4-difluoro-n-butyl, 4,4,4-trifluoro-n-butyl, (C2-C6) haloalkenyl, (C2-C6) haloalkynyl, (C 3 - C 6 ) - Halocycloalkyl, (C 4 -C 6) -cycloalkenyl, (C 4 -C 6) -halocycloalkenyl, methoxymethyl, ethoxymethyl, ethoxyethyl, methoxyethyl, methoxy-n-propyl, ethoxy-n-propyl, methoxybutyl, methoxy-iso Propyl, iso-propoxymethyl, iso-propoxyethyl, optionally substituted phenyl, aryl- (Ci-C6) -alkyl, heteroaryl, heteroaryl (Ci -C 6 ) -alkenyl, (C -C 6 ) -Cycloal kenyl- (Ci -C 6) -alkyl, (Ci-C6) -alkyl koxycarbonyl- (Ci-C6) -alkyl, (C 2 -C 6) -alkyl kenyloxycarbonyl- (Ci-C6) -alkyl, aryl - (C 1 -C 6 ) - AI koxycarbonyl- (Ci -C6) -al kyl, hydroxycarbonyl (Ci -C6) -al kyl, heterocyclyl, heterocyclyl- (Ci-C6) alkyl and represents hydrogen, methyl, ethyl, n-propyl, 1-methylethyl , n-butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 2,2 -Dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-di-methylbutyl, 2.2 - Dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2-trimethylpropyl, 1, 2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1 - ethyl 2-methylpropyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyanomethyl, cyanoethyl, cyano-n-propyl, cyano-n-butyl, ethenyl, 1-propenyl, 2-propenyl, 1-methyl-ethenyl, 1-butenyl, 2 -Butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl 1- 2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl 2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, 1-dimethyl 2-propenyl, 1, 2-dimethyl-1-propenyl, 1, 2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3- Hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4- Methyl 3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1, 1-dimethyl-2-butenyl, 1, 1-dimethyl-3-butenyl, 1, 2-dimethyl-1-butenyl, 1, 2-dimethyl-2-butenyl, 1, 2-dimethyl-3-butenyl, 1, 3-dimethyl-1-butenyl, 1, 3-Dimethyl-2-butenyl, 1, 3-dimethyl-3-butenyl, 2,2-dimethyl 3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl -2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3 -butenyl, 1, 1, 2-thmethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl , Ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl 2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1 - butinyl, 1, 1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1 - Methyl 3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl 1-pentynyl, 4-methyl-2-pentynyl, 1, 1-dimethyl-2-butynyl, 1, 1-dimethyl-3-butynyl, 1, 2-dimethyl-3-butynyl, 2,2-dimethyl-3 butinyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl, cyclopropyl, Cyclobutyl, cyclopentyl, cyclohexyl, spiro [2.2] pent-1-yl, spiro [2.3] hex-1-yl, spiro [2.3] hex-4-yl, 3-spiro [2.3] hex-5-yl, spiro [3.3] hept-1-yl, spiro [3.3] hept-2-yl, bicyclo [1-1.0] butan-1-yl,
Bicyclo[1 .1 .0]butan-2-yl, Bicyclo[2.1 .0]pentan-1 -yl, Bicyclo[1 .1 .1 ]pentan-1 -yl, Bicyclo[2.1 .0]pentan-2-yl, Bicyclo[2.1 .0]pentan-5-yl, Bicyclo[2.1 .1 ]hexyl, Bicyclo [1-1, 0] butan-2-yl, bicyclo [2.1.0] pentan-1-yl, bicyclo [1,11,1] pentan-1-yl, bicyclo [2.1.0] pentan-2-yl yl, bicyclo [2.1.0] pentan-5-yl, bicyclo [2.1.1] hexyl,
Bicyclo[2.2.1 ]hept-2-yl, Bicyclo[2.2.2]octan-2-yl, Bicyclo[3.2.1]octan-2-yl, Bicyclo[3.2.2]nonan-2-yl, Adamantan-1 -yl, Adamantan-2-yl, 1 - Methylcyclopropyl, 2-Methylcyclopropyl, 2,2-Dimethylcyclopropyl, 2,3- Dimethylcyclopropyl, 1 ,1 '-Bi(cyclopropyl)-1 -yl, 1 ,1 '-Bi(cyclopropyl)-2-yl, 2'- Methyl-1 ,1 '-bi(cyclopropyl)-2-yl, 2-Cyanocyclopropyl, 1 -Methylcyclobutyl, 2- Methylcyclobutyl, 3-Methylcyclobutyl, 2-Cyanocyclobutyl, 3-Cyanocyclobutyl, 3- Methoxycyclobutyl, 1 -AI lyl cyclopropyl, 1 -Ethylcyclopropyl, 1 -Methylcyclohexyl, 2-Methylcyclohexyl, 3-Methylcyclohexyl, 2-Methoxycyclohexyl, 3- Methoxycyclohexyl, 4-Methoxycyclohexyl, Cyclopropylnnethyl, Cyclobutylnnethyl, Cyclopentyl methyl, Cyclohexylmethyl, Trifluormethyl, Pentafluorethyl, 1 ,1 ,2,2- Tetrafluorethyl, Heptafluorpropyl, Nonafluorbutyl, Chlordifluormethyl, Bicyclo [2.2.1] hept-2-yl, bicyclo [2.2.2] octan-2-yl, bicyclo [3.2.1] octan-2-yl, bicyclo [3.2.2] nonan-2-yl, adamantane 1 -yl, adamantan-2-yl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, 2,3-dimethylcyclopropyl, 1,1'-bis (cyclopropyl) -1-yl, 1,1 '-Bi (cyclopropyl) -2-yl, 2'-methyl-1, 1 '-bi (cyclopropyl) -2-yl, 2-cyanocyclopropyl, 1-methylcyclobutyl, 2-methylcyclobutyl, 3-methylcyclobutyl, 2-cyanocyclobutyl, 3-cyanocyclobutyl , 3-methoxycyclobutyl, 1-allylcyclopropyl, 1-ethylcyclopropyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 2-methoxycyclohexyl, 3-methoxycyclohexyl, 4-methoxycyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, trifluoromethyl, Pentafluoroethyl, 1,1,2,2-tetrafluoroethyl, heptafluoropropyl, nonafluorobutyl, chlorodifluoromethyl,
Bromdifluormethyl, Dichlorfluormethyl, loddifluormethyl, Bromfluormethyl, 1 - Fluorethyl, 2-Fluorethyl, Fluormethyl, Difluormethyl, 2,2-Difluorethyl, 2,2,2- Trifluorethyl, 3,3,3-Trifluor-n-propyl, Difluor-tert.-butyl, (C2-C6)-Haloalkenyl, (C2-C6)-Haloalkinyl, (C3-C6)-Halocycloalkyl, (C -C6)-Cycloalkenyl, (C -C6)- Halocycloalkenyl, Methoxymethyl, Ethoxymethyl, Ethoxyethyl, Methoxyethyl, Methoxy-n-propyl, Ethoxy-n-propyl, Methoxybutyl, Methoxy-iso-Propyl, iso- Propoxy methyl, iso-Propoxyethyl, gegebenenfalls substituiertes Phenyl, Aryl- (Ci-C6)-alkyl, Heteroaryl, Heteroaryl-(Ci-C6)-alkyl, Heterocyclyl-(Ci-C6)-alkyl, (C4-C6)-Cycloalkenyl-(Ci-C6)-alkyl, NR21R22 steht. Im Speziellen bevorzugt sind Verbindungen der allgemeinen Formel (I), die durch die Formeln (la) bis (Iz) beschrieben werden,Bromodifluoromethyl, dichlorofluoromethyl, iododifluoromethyl, bromofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, fluoromethyl, difluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 3,3,3-trifluoro-n-propyl, difluoro-tert. -butyl, (C2-C6) haloalkenyl, (C2-C6) haloalkynyl, (C3-C 6) halocycloalkyl, (C-C6) cycloalkenyl, (C-C6) - Halocycloalkenyl, methoxymethyl, ethoxymethyl , Ethoxyethyl, methoxyethyl, methoxy-n-propyl, ethoxy-n-propyl, methoxybutyl, methoxy-isopropyl, isopropoxy-methyl, isopropoxyethyl, optionally substituted phenyl, aryl- (C 1 -C 6) -alkyl, heteroaryl, Heteroaryl- (C 1 -C 6 ) -alkyl, heterocyclyl- (C 1 -C 6 ) -alkyl, (C 4 -C 6 ) -cycloalkenyl- (C 1 -C 6 ) -alkyl, NR 21 R 22 . Especially preferred are compounds of the general formula (I) which are described by the formulas (Ia) to (Iz)
(Ιζ) worin R1, R2 und R7 unabhängig voneinander für Wasserstoff, Fluor, Chlor, Brom, lod,(Ι ζ ) in which R 1 , R 2 and R 7 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine,
Cyano, Nitro, NR21R22, OR23, S(O)nR24, Thiocyanato, Isothiocyanato, Methyl, Ethyl, n-Propyl, 1 -Methylethyl, n-Butyl, 1 -Methyl propyl, 2-Methylpropyl, 1 ,1 - Dimethylethyl, n-Pentyl, 1 -Methylbutyl, 2-Methylbutyl, 3-Methylbutyl, 1 ,1 - Dimethylpropyl, 1 ,2-Dimethylpropyl, 2,2-Dimethylpropyl, 1 -Ethylpropyl, Cyano, nitro, NR 21 R 22 , OR 23 , S (O) n R 24 , thiocyanato, isothiocyanato, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1 , 1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl,
Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl, Cyclohexylmethyl, gegebenenfalls substituiertes Phenyl, Heteroaryl, Heterocyclyl, Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Adamantan-1 -yl, Adamantan-2-yl, 1 - Methylcyclopropyl, 2-Methylcyclopropyl, 2,2-Dimethylcyclopropyl, 2,3- Dimethylcyclopropyl, 1 ,1 '-Bi(cyclopropyl)-1 -yl, 1 ,1 '-Bi(cyclopropyl)-2-yl, 2'- Methyl-1 ,1 '-bi(cyclopropyl)-2-yl, Ethenyl, 1 -Propenyl, 2-Propenyl, 1 -Methyl- ethenyl, 1 -Butenyl, 2-Butenyl, 3-Butenyl, 1 -Methyl-1 -propenyl, 2-Methyl-1 - propenyl, 1 -Methyl-2-propenyl, 2-Methyl-2-propenyl, Ethinyl, 1 -Propinyl, 2- Propinyl, 1 -Butinyl, 2-Butinyl, 3-Butinyl, 1 -Methyl-2-propinyl, Methoxymethyl, Ethoxymethyl, Ethoxyethyl, Methoxyethyl, Methoxy-n-propyl, Ethoxy-n-propyl, Methoxybutyl, Trifluormethyl, Pentafluorethyl, 1 ,1 ,2,2-Tetrafluorethyl,  Cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, optionally substituted phenyl, heteroaryl, heterocyclyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantan-1-yl, adamantan-2-yl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, 2,3-Dimethylcyclopropyl, 1,1 '-Bi (cyclopropyl) -1-yl, 1,1' -Bi (cyclopropyl) -2-yl, 2'-methyl-1,1 '-bi (cyclopropyl) -2 -yl, ethenyl, 1-propenyl, 2-propenyl, 1-methyl-ethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl 2-propenyl, 2-methyl-2-propenyl, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, methoxymethyl, ethoxymethyl, ethoxyethyl, methoxyethyl , Methoxy-n-propyl, ethoxy-n-propyl, methoxybutyl, trifluoromethyl, pentafluoroethyl, 1,1,2,2-tetrafluoroethyl,
Heptafluorpropyl, Nonafluorbutyl, Chlordifluormethyl, 1 -Fluorethyl, 2-Fluorethyl, Fluormethyl, Difluormethyl, 2,2-Difluorethyl, 2,2,2-Trifluorethyl, Difluor-tert.-butyl Trifluormethoxymethyl, Trifluormethoxyethyl, Trifluormethoxy-n-propyl,  Heptafluoropropyl, nonafluorobutyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, fluoromethyl, difluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, difluoro-tert-butyl trifluoromethoxymethyl, trifluoromethoxyethyl, trifluoromethoxy-n-propyl,
Difluormethoxymethyl, Difluormethoxyethyl, Difluormethoxy-n-propyl, 2,2- Difluorethoxymethyl, 2,2-Difluorethoxyethyl, 2,2-Difluorethoxy-n-propyl, 2,2,2- Trifluorethoxymethyl, 2,2,2-Trifluorethoxyethyl, 2,2,2-Trifluorethoxy-n-propyl, Pentafluorethoxymethyl, Pentafluorethoxyethyl, Pentafluorethoxy-n-propyl, Methylthiomethyl, Methylthioethyl, Ethylthioethyl, Trifluormethylthiomethyl, Trifluormethylthioethyl, 1 -Cyclopentenyl, 2-Cyclopentenyl, 3-Cyclopentenyl, 1 - Cyclohexenyl, 2-Cyclohexenyl, 3-Cyclohexenyl, Methoxymethoxymethyl, Methoxyethoxymethyl, Methoxyethoxyethyl, Methoxymethoxyethyl, Ethoxy-n- propoxymethyl, Ethoxy-n-propoxyethyl, Ethoxyethoxymethyl, Ethoxyethoxyethyl Fluorethinyl, Chlorethinyl, Trifluormethylethinyl, Pentafluorthio, Aryl-(Ci-C6)- alkyl, Heteroaryl-(Ci-C6)-alkyl, Heterocyclyl-(Ci-C6)-alkyl, Methylcarbonylmethyl Methylcarbonylethyl, Methylcarbonyl-n-propyl, COOR23, CONR21R22, COR23 , - C=NOR23, R21 R22N-(Ci-C6)-alkyl, R23OOC-(Ci-C6)-alkyl, Aryl-(Ci-C6)-alkinyl, Heteroaryl-(Ci-C6)-alkinyl, Heterocyclyl-(Ci-C6)-alkinyl, Trimethylsilylethinyl, Triethylsilylethinyl, Tris-(iso-propyl)silylethinyl, Cyclopropylethinyl, Cyclobutylethinyl, Cyclopentylethinyl, Cyclohexylethinyl, Aryl-(C2-C6)-alkenyl, Heteroaryl-(C2-C6)-alkenyl, Heterocyclyl-(C2-C6)-alkenyl, (C1-C6)- Alkylaminosulfonylannino, (C3-C6)-Cycloalkylaminosulfonylannino, Diazo, Difluoromethoxymethyl, difluoromethoxyethyl, difluoromethoxy-n-propyl, 2,2-difluoroethoxymethyl, 2,2-difluoroethoxyethyl, 2,2-difluoroethoxy-n-propyl, 2,2,2-trifluoroethoxymethyl, 2,2,2-trifluoroethoxyethyl, 2, 2,2-trifluoroethoxy-n-propyl, pentafluoroethoxymethyl, pentafluoroethoxyethyl, pentafluoroethoxy-n-propyl, methylthiomethyl, methylthioethyl, ethylthioethyl, trifluoromethylthiomethyl, trifluoromethylthioethyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, methoxymethoxymethyl, methoxyethoxymethyl, methoxyethoxyethyl, methoxymethoxyethyl, ethoxy-n-propoxymethyl, ethoxy-n-propoxyethyl, ethoxyethoxymethyl, ethoxyethoxyethyl, fluoroethynyl, chloroethynyl, trifluoromethylethynyl, pentafluorothio, aryl- (C 1 -C 6) -alkyl, heteroaryl- (ci) C6) -alkyl, heterocyclyl- (C 1 -C 6) -alkyl, methylcarbonylmethyl, methylcarbonylethyl, methylcarbonyl-n-propyl, COOR 23 , CONR 21 R 22 , COR 23 , -C = NOR 23 , R 21 R 22 N- C 6 ) -alkyl, R 23 OOC- (C 1 -C 6 ) -alkyl, aryl- (Ci -C 6 ) -alkynyl, heteroaryl- (C 1 -C 6 ) -alkynyl, heterocyclyl- (C 1 -C 6 ) -alkynyl, trimethylsilylethynyl, triethylsilylethynyl, tris (iso-propyl) silylethynyl, cyclopropylethynyl, Cyclobutylethynyl, cyclopentylethynyl, cyclohexylethynyl, aryl- (C 2 -C 6) -alkenyl, heteroaryl- (C 2 -C 6) -alkenyl, heterocyclyl- (C 2 -C 6) -alkenyl, (C 1 -C 6) -alkylaminosulfonylannino, (C 3 -C 6) - Cycloalkylaminosulfonylannino, Diazo,
Aryldiazo, Trimethylsilyl stehen,  Aryldiazo, trimethylsilyl,
X1, X2 und X3 gleich oder verschieden sind und unabhängig voneinander für O X 1 , X 2 and X 3 are the same or different and are each independently O.
(Sauerstoff), S (Schwefel), N (Stickstoff), die Gruppierung C-R2 oder die (Oxygen), S (sulfur), N (nitrogen), the group CR 2 or the
Gruppierung N-R20 stehen, wobei jedoch in keinem Fall ein O- und S-Atom benachbart sind und wobei in keinem Fall jeweils mehr als ein O- oder S-Atom im gebildeten 5-gliedrigen Ring enthalten ist, und wobei R2 in der Gruppierung C-R2 und R20 in der Gruppierung N-R20 jeweils gleiche oder verschiedene Bedeutungen gemäß der oben- oder nachstehenden Definitionen haben, Grouping NR 20 are, but in no case adjacent to an O and S atom and in each case in each case more than one O or S atom in the formed 5-membered ring is contained, and wherein R 2 in the grouping CR 2 and R 20 in moiety NR 20 each have the same or different meanings according to the above or below definitions,
W für O (Sauerstoff) oder S (Schwefel) steht, W is O (oxygen) or S (sulfur),
A1, A2, A3, A4 und A5 gleich oder verschieden sind und unabhängig voneinander für N (Stickstoff) oder die Gruppierung C-R7 stehen, wobei jedoch in keinem Fall mehr als zwei N-Atome benachbart sind, und wobei R7 in der Gruppierung C-R7 jeweils gleiche oder verschiedene Bedeutungen gemäß der oben stehenden Definition hat, A 1 , A 2 , A 3 , A 4 and A 5 are the same or different and are independently N (nitrogen) or the group CR 7 , but in no case more than two N atoms are adjacent, and wherein R 7 in the group CR 7 has the same or different meanings as defined above,
R5 und R6 unabhängig voneinander für Wasserstoff, Methyl, Ethyl, n-Propyl, 1 - Methylethyl, n-Butyl, 1 -Methylpropyl, 2-Methylpropyl, 1 ,1 -Dimethylethyl, n- Pentyl, 1 -Methylbutyl, 2-Methylbutyl, 3-Methylbutyl, 1 ,1 -Dimethylpropyl, 1 ,2- Dimethylpropyl, 2,2-Dimethylpropyl, 1 -Ethylpropyl, n-Hexyl, Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl, Cyclohexylmethyl, Cyanomethyl, R 5 and R 6 independently of one another represent hydrogen, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, n-pentyl, 1-methylbutyl, 2 Methylbutyl, 3-methylbutyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyanomethyl,
Cyanoethyl, Cyano-n-propyl, Cyano-n-butyl, Ethenyl, 1 -Propenyl, 2-Propenyl, 1 - Methyl-ethenyl, 1 -Butenyl, 2-Butenyl, 3-Butenyl, 1 -Methyl-1 -propenyl, 2-Methyl- 1 -propenyl, 1 -Methyl-2-propenyl, 2-Methyl-2-propenyl, Ethinyl, 1 -Propinyl, 2- Propinyl, 1 -Butinyl, 2-Butinyl, 3-Butinyl, 1 -Methyl-2-propinyl, 1 -Pentinyl, 2- Pentinyl, 3-Pentinyl, 4-Pentinyl, Trifluormethyl, Pentafluorethyl, 1 ,1 ,2,2- Tetrafluorethyl, Heptafluorpropyl, Nonafluorbutyl, 1 -Fluorethyl, 2-Fluorethyl, Fluormethyl, Difluormethyl, 1 ,1 -Difluorethyl, 2,2-Difluorethyl, 2,2,2-Trifluorethyl, 3,3,3-Trifluor-n-propyl, Difluor-tert.-butyl, Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, gegebenenfalls substituiertes Phenyl, Aryl, Aryl-(Ci -C5)-alkyl, Heteroaryl, Heteroaryl-(Ci -C5)-alkyl, Heterocyclyl, Heterocyclyl-(Ci -C5)-alkyl, Methoxymethyl, Ethoxymethyl, Ethoxyethyl, Methoxyethyl, Methoxy-n-propyl, Ethoxy-n-propyl, Methoxybutyl, iso-Propoxymethyl, iso-Propoxyethyl, Cyanoethyl, cyano-n-propyl, cyano-n-butyl, ethenyl, 1-propenyl, 2-propenyl, 1-methyl-ethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl 2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, trifluoromethyl, pentafluoroethyl, 1,1,2,2-tetrafluoroethyl, heptafluoropropyl, nonafluorobutyl, 1-fluoroethyl, 2-fluoroethyl, fluoromethyl, difluoromethyl, 1, 1 -difluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 3,3,3-trifluoro-n-propyl, difluoro-tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, Cyclohexyl, optionally substituted phenyl, aryl, aryl- (C 1 -C 5) -alkyl, heteroaryl, heteroaryl- (C 1 -C 5) -alkyl, heterocyclyl, heterocyclyl- (C 1 -C 5) -alkyl, methoxymethyl, ethoxymethyl, ethoxyethyl, methoxyethyl, Methoxy-n-propyl, ethoxy-n-propyl, methoxybutyl, iso-propoxymethyl, iso-propoxyethyl,
Trifluormethoxymethyl, Trifluormethoxyethyl, Trifluormethoxy-n-propyl, 2,2- Difluorethoxymethyl, 2,2-Difluorethoxyethyl, 2,2-Difluorethoxy-n-propyl, 2,2,2- Trifluorethoxymethyl, 2,2,2-Trifluorethoxyethyl, 2,2,2-Trifluorethoxy-n-propyl, Pentafluorethoxymethyl, Pentafluorethoxyethyl, Pentafluorethoxy-n-propyl, Methylthiomethyl, Methylthioethyl, Ethylthioethyl, Methylthio-n-propyl, Ethylthio- n-propyl, Trifluormethylthiomethyl, Trifluormethylthioethyl, Trifluormethylthio-n- propyl, COOR23, CONR21R22, Hydroxycarbonylmethyl, Hydroxycarbonylethyl, Hydroxycarbonyl-n-propyl, Methoxycarbonylmethyl, Ethoxycarbonylmethyl, n- Propyloxycarbonylmethyl, iso-Propyloxycarbonylmethyl, tert.- Butyloxycarbonylmethyl, Methoxycarbonylethyl, Ethoxycarbonylethyl, n- Propyloxycarbonylethyl, iso-Propyloxycarbonylethyl, tert.-Butyloxycarbonylethyl Methoxycarbonyl-n-propyl, Ethoxycarbonyl-n-propyl, n-Propyloxycarbonyl-n- propyl, iso-Propyloxycarbonyl-n-propyl, tert.-Butyloxycarbonyl-n-propyl, Trifluoromethoxymethyl, trifluoromethoxyethyl, trifluoromethoxy-n-propyl, 2,2-difluoroethoxymethyl, 2,2-difluoroethoxyethyl, 2,2-difluoroethoxy-n-propyl, 2,2,2-trifluoroethoxymethyl, 2,2,2-trifluoroethoxyethyl, 2, 2,2-trifluoroethoxy-n-propyl, pentafluoroethoxymethyl, pentafluoroethoxyethyl, pentafluoroethoxy-n-propyl, methylthiomethyl, methylthioethyl, ethylthioethyl, methylthio-n-propyl, ethylthio-n-propyl, trifluoromethylthiomethyl, trifluoromethylthioethyl, trifluoromethylthio-n-propyl, COOR 23 , CONR 21 R 22, hydroxycarbonylmethyl, hydroxycarbonylethyl, hydroxycarbonyl-n-propyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, n- Propyloxycarbonylmethyl, iso-Propyloxycarbonylmethyl, tert-Butyloxycarbonylmethyl, methoxycarbonylethyl, ethoxycarbonylethyl, n-Propyloxycarbonylethyl, iso-Propyloxycarbonylethyl, tert-methoxycarbonyl Butyloxycarbonylethyl -n-propyl, ethoxycarbonyl-n-propyl, n-propyloxycarbonyl-n-propyl, iso-propyloxycarbonyl-n-propyl, tert-butyloxycarbonyl-n-propyl,
Allyloxycarbonylmethyl, Allyloxycarbonylethyl, Allyloxycarbonyl-n-propyl, Propargyloxycarbonylmethyl, Propargyloxycarbonylethyl, Propargyloxycarbonyl n-propyl, Phenylmethyloxycarbonylmethyl, Phenylmethyloxycarbonylethyl, Phenylmethyloxycarbonyl-n-propyl, Heteroaryl-(Ci -C5)-alkoxycarbonyl-(Ci -C5)- al kyl , Heterocyclyl-(Ci -Cs)-al koxycarbonyl-(Ci-Cs)-al kyl stehen , und X1, wenn X1 für eine Gruppe C-R2 steht, mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig Allyloxycarbonylmethyl, allyloxycarbonylethyl, allyloxycarbonyl-n-propyl, propargyloxycarbonylmethyl, propargyloxycarbonylethyl, propargyloxycarbonyl, n-propyl, phenylmethyloxycarbonylmethyl, phenylmethyloxycarbonylethyl, phenylmethyloxycarbonyl-n-propyl, heteroaryl- (C 1 -C 5) -alkoxycarbonyl- (C 1 -C 5) -alkyl, heterocyclyl- (Ci-Cs) -al koxycarbonyl- (Ci-Cs) -al kyl, and X 1 , when X 1 is a group CR 2 , with the atoms to which they are attached, a fully saturated, partially saturated or completely
ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden, und X2, wenn beide für eine Gruppe C-R2 stehen, mit den Atomen, an die sie form unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring, and X 2 , when both represent a group CR 2 , with the atoms to which they
gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden, A1 und A2, wenn beide für eine Gruppe C-R7 stehen, mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden, form a fully saturated, partially saturated or fully unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring, A 1 and A 2 , when both represent a group CR 7 , with the atoms to which they are attached form a fully saturated, partially saturated or completely unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring,
A2 und A3, wenn beide für eine Gruppe C-R7 stehen, mit den Atomen, an die sie A 2 and A 3 , when both represent a group CR 7 , with the atoms to which they belong
gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden und  form a fully saturated, partially saturated or fully unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5-7-membered ring and form
A3 und A4, wenn beide für eine Gruppe C-R7 stehen, mit den Atomen, an die sie A 3 and A 4 , when both represent a group CR 7 , with the atoms to which they belong
gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden,  form a fully saturated, partially saturated or fully unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring,
Y für eine Bindung oder für die Gruppierungen Y-1 bis Y-7 Y for a bond or for the groupings Y-1 to Y-7
steht, wobei R8, R9, R10, R1 1, R12, R13, R14, R15, R16, R17, R18 und R19 jeweils die , wherein R 8, R 9, R 10, R 1 1, R 12, R 13, R 14, R 15, R 16, R 17, R 18 and R 19 in each case the
Bedeutung gemäß der nachstehenden Definition haben und wobei der Pfeil für eine Bindung zum 6-gliedrigen Ring mit den Gruppierungen A1, A2, A3, A4 und A5 steht, R8, R9, R10, R1 1, R12, R13, R14, R15, R16, R17, R18 und R19 unabhängig voneinander für Wasserstoff, Fluor, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, iso-Butyl, tert.- Butyl, Ethenyl, 1 -Propenyl, 2-Propenyl, 1 -Methyl-ethenyl, 1 -Butenyl, 2-Butenyl, 3-Butenyl, 1 -Methyl-1 -propenyl, 2-Methyl-1 -propenyl, 1 -Methyl-2-propenyl, 2- Methyl-2-propenyl, Ethinyl, 1 -Propinyl, 2-Propinyl, 1 -Butinyl, 2-Butinyl, 3-Butinyl, 1 -Methyl-2-propinyl, Thfluormethyl, Pentafluorethyl, 1 ,1 ,2,2-Tetrafluorethyl, Heptafluorpropyl, Nonafluorbutyl, Chlordifluormethyl, 1 -Fluorethyl, 2-Fluorethyl, Fluormethyl, Difluormethyl, 1 ,1 -Difluorethyl, 2,2-Difluorethyl, 2,2,2-Trifluorethyl, 3,3,3-Trifluor-n-propyl, Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl, Cyclohexylmethyl, gegebenenfalls substituiertes Phenyl, Aryl-(Ci-C6)-alkyl, Heteroaryl, Heteroaryl- (Ci-C6)-alkyl, Heterocyclyl, Heterocyclyl-(Ci-C6)-alkyl, Methoxymethyl, Have meaning as defined below and wherein the arrow represents a bond to the 6-membered ring with the groupings A 1 , A 2 , A 3 , A 4 and A 5 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 independently of one another are hydrogen, fluorine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, ethenyl, 1-propenyl, 2-propenyl, 1-methyl-ethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, thfluoromethyl, pentafluoroethyl, 1,1,2,2-tetrafluoroethyl, heptafluoropropyl, nonafluorobutyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, fluoromethyl, difluoromethyl, 1, 1-difluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 3,3,3-trifluoro-n-propyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, optionally substituted phenyl, Aryl- (C 1 -C 6) -alkyl, heteroaryl, heteroaryl- (C 1 -C 6) -alkyl, heterocyclyl, heterocyclyl- (C 1 -C 6) -alkyl, methoxymethyl,
Ethoxymethyl, Ethoxyethyl, Methoxyethyl, Methoxy-n-propyl, Ethoxy-n-propyl, Methoxybutyl, Methoxy-iso-propyl, iso-Propoxymethyl, iso-Propoxyethyl, Trifluormethoxymethyl, Trifluormethoxyethyl, Trifluormethoxy-n-propyl,  Ethoxymethyl, ethoxyethyl, methoxyethyl, methoxy-n-propyl, ethoxy-n-propyl, methoxybutyl, methoxy-isopropyl, iso-propoxymethyl, iso-propoxyethyl, trifluoromethoxymethyl, trifluoromethoxyethyl, trifluoromethoxy-n-propyl,
Difluormethoxymethyl, Difluormethoxyethyl, Difluormethoxy-n-propyl, 2,2,2- Trifluorethoxymethyl, 2,2,2-Trifluorethoxyethyl, 2,2,2-Trifluorethoxy-n-propyl, Pentaf I uorethoxymethyl , Pentaf I uorethoxyethyl , Pentafl uorethoxy-n-propyl , Methylthiomethyl, Methylthioethyl, Ethylthioethyl, Methylthio-n-propyl, Ethylthio- n-propyl, Trifluormethylthiomethyl, Trifluormethylthioethyl, Trifluormethylthio-n- propyl, COOR23 stehen, und R6 mit dem Atom, an das sie gebunden sind, einen vollständig gesättigten, oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden, für Wasserstoff, Methyl, Ethyl, n-Propyl, 1 -Methylethyl, n-Butyl, 1 -Methylpropyl, 2-Methylpropyl, 1 ,1 -Dimethylethyl, n-Pentyl, 1 -Methylbutyl, 2-Methylbutyl, 3- Methylbutyl, 1 ,1 -Dimethylpropyl, 1 ,2-Dimethylpropyl, 2,2-Dimethylpropyl, 1 - Ethylpropyl, n-Hexyl, Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl, Cyclohexylmethyl, Cyanomethyl, Cyanoethyl, Cyano-n-propyl, Cyano-n-butyl, Ethenyl, 1 -Propenyl, 2-Propenyl, 1 -Methyl-ethenyl, 1 -Butenyl, 2-Butenyl, 3- Butenyl, 1 -Methyl-1 -propenyl, 2-Methyl-1 -propenyl, 1 -Methyl-2-propenyl, 2- Methyl-2-propenyl, 1 -Pentenyl, 2-Pentenyl, 3-Pentenyl, 4-Pentenyl, 1 -Methyl-1 - butenyl, 2-Methyl-1 -butenyl, 3-Methyl-1 -butenyl, 1 -Methyl-2-butenyl, 2-Methyl-2 butenyl, 3-Methyl-2-butenyl, 1 -Methyl-3-butenyl, 2-Methyl-3-butenyl, 3-Methyl-3 butenyl, 1 ,1 -Dimethyl-2-propenyl, 1 ,2-Dimethyl-1 -propenyl, 1 ,2-Dimethyl-2- propenyl, 1 -Ethyl-1 -propenyl, 1 -Ethyl-2-propenyl, Ethinyl, 1 -Propinyl, 2-Propinyl, 1 -Butinyl, 2-Butinyl, 3-Butinyl, 1 -Methyl-2-propinyl, 1 -Pentinyl, 2-Pentinyl, 3- Pentinyl, 4-Pentinyl, 1 -Methyl-2-butinyl, 1 -Methyl-3-butinyl, 2-Methyl-3-butinyl, 3 Methyl-1 -butinyl, 1 ,1 -Dimethyl-2-propinyl, 1 -Ethyl-2-propinyl, Methoxy, Ethoxy, n-Propyloxy, iso-Propyloxy, n-Butyloxy, tert.-Butyloxy, 2,2-Difluorethyl, 2,2,2- Trifluorethyl, 3,3,3-Trifluor-n-propyl, Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Spiro[2.2]pent-1 -yl, Spiro[2.3]hex-1 -yl, Spiro[2.3]hex-4-yl, 3- Spiro[2.3]hex-5-yl, Spiro[3.3]hept-1 -yl, Spiro[3.3]hept-2-yl, Bicyclo[1 .1 .0]butan-1 yl, Bicyclo[1 .1 .0]butan-2-yl, Bicyclo[2.1 .0]pentan-1 -yl, Bicyclo[1 .1 .1 ]pentan-1 -yl, Bicyclo[2.1 .0]pentan-2-yl, Bicyclo[2.1 .0]pentan-5-yl, Bicyclo[2.1 .1]hexyl, Difluoromethoxymethyl, difluoromethoxyethyl, difluoromethoxy-n-propyl, 2,2,2-trifluoroethoxymethyl, 2,2,2-trifluoroethoxyethyl, 2,2,2-trifluoroethoxy-n-propyl, pentafluoroethoxymethyl, pentafluoroethoxyethyl, pentafluoroethoxy-n -propyl, methylthiomethyl, methylthioethyl, ethylthioethyl, methylthio-n-propyl, ethylthio-n-propyl, trifluoromethylthiomethyl, trifluoromethylthioethyl, trifluoromethylthio-n-propyl, COOR 23 , and R 6 with the atom to which they are attached, a complete form saturated, or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring, for hydrogen, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, cyclopropylmethyl, cyclobutylmethyl, Cyclopentylmethyl, cyclohexylmethyl, cyanomethyl 1, cyanoethyl, cyano-n-propyl, cyano-n-butyl, ethenyl, 1-propenyl, 2-propenyl, 1-methyl-ethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1 - propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl 3-butenyl, 3-methyl-3-butenyl, 1, 1-dimethyl-2-propenyl, 1, 2-dimethyl-1-propenyl, 1, 2-dimethyl-2- propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1 - Pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl 2-propynyl, 1-ethyl-2-propynyl, methoxy, ethoxy, n-propyloxy, isopropoxy, n-butyloxy, tert -butyloxy, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 3, 3,3-trifluoro-n-propyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, spiro [2.2] pent-1-yl, spiro [2.3] hex-1-yl, spiro [2.3] hex-4-yl, 3 Spiro [2.3] hex-5-yl, spiro [3.3] hept-1-yl, spiro [3.3] hept-2-yl, bicyclo [1 .1] butan-1-yl, bicyclo [1 .1 .0 ] butan-2-yl, bicyclo [2.1.0] pentan-1-yl, bicyclo [1,11,1] pentan-1-yl, bicyclo [2.1.0] pentan-2-yl, bicyclo [2.1 .0 ] pentan-5-yl, bicyclo [2.1.1] hexyl,
Bicyclo[2.2.1 ]hept-2-yl, Bicyclo[2.2.2]octan-2-yl, Bicyclo[3.2.1]octan-2-yl, Bicyclo[3.2.2]nonan-2-yl, Adamantan-1 -yl, Adamantan-2-yl, 1 - Methylcyclopropyl, 2-Methylcyclopropyl, 2,2-Dimethylcyclopropyl, 2,3- Dimethylcyclopropyl, 1 ,1 '-Bi(cyclopropyl)-1 -yl, 1 ,1 '-Bi(cyclopropyl)-2-yl, 2'- Methyl-1 ,1 '-bi(cyclopropyl)-2-yl, gegebenenfalls substituiertes Phenyl, Bicyclo [2.2.1] hept-2-yl, bicyclo [2.2.2] octan-2-yl, bicyclo [3.2.1] octan-2-yl, bicyclo [3.2.2] nonan-2-yl, adamantane 1 -yl, adamantan-2-yl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, 2,3-dimethylcyclopropyl, 1,1'-bis (cyclopropyl) -1-yl, 1,1 '-Bi (cyclopropyl) -2-yl, 2'-methyl-1, 1 '-bi (cyclopropyl) -2-yl, optionally substituted phenyl,
Heteroaryl, Heterocyclyl, Methylcarbonyl, Ethylcarbonyl, iso-Propylcarbonyl, n- Butylcarbonyl, iso-Butylcarbonyl, tert.-Butylcarbonyl, Aryl-(Ci-C5)-Alkylcarbonyl, Cyclopropylcarbonyl, Cyclobutylcarbonyl, Cyclopentylcarbonyl, Heteroaryl, heterocyclyl, methylcarbonyl, ethylcarbonyl, isopropylpolyyl, n-butylcarbonyl, isobutylcarbonyl, tert-butylcarbonyl, aryl- (C 1 -C 5) -alkylcarbonyl, cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl,
Cyclohexylcarbonyl, Arylcarbonyl, Heteroarylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl, iso-Propyloxycarbonyl, tert.-Butyloxycarbonyl, Allyloxycarbonyl Aryl-(Ci-C5)-alkoxycarbonyl, Heteroaryl-(Ci-C5)-alkoxycarbonyl, Cyclohexylcarbonyl, arylcarbonyl, heteroarylcarbonyl, methoxycarbonyl, ethoxycarbonyl, isopropyloxycarbonyl, tert-butyloxycarbonyl, allyloxycarbonyl, aryl- (C 1 -C 5) -alkoxycarbonyl, heteroaryl- (C 1 -C 5) -alkoxycarbonyl,
Cyclopropylmethoxycarbonyl, Cyclobutylmethoxycarbonyl, Cyclopropylmethoxycarbonyl, cyclobutylmethoxycarbonyl,
Cyclopentyl methoxycarbonyl, Cyclohexylmethoxycarbonyl, Methylsulfonyl, Ethylsulfonyl, n-Propylsulfonyl, iso-Propylsulfonyl, n-Butylsulfonyl, iso- Butylsulfonyl, tert.-Butylsulfonyl, Trifluormethylsulfonyl, Cyclopropylsulfonyl, Cyclobutylsulfonyl, Cyclopentylsulfonyl, Cyclohexylsulfonyl, Arylsulfonyl, Heteroarylsulfonyl, Arylsulfinyl, Heteroarylsulfinyl, Methylsulfinyl, Ethylsulfinyl, n Propylsulfinyl, iso-Propylsulfinyl, n-Butylsulfinyl, iso-Butylsulfinyl, tert.- Butylsulfinyl, Trifluormethylsulfinyl, Cyclopropylsulfinyl, Cyclobutylsulfinyl, Cyclopentylsulfinyl, Cyclohexylsulfinyl steht, für 0, 1 oder 2 steht R22 gleich oder verschieden sind und unabhängig voneinander für Cyclopentyl methoxycarbonyl, Cyclohexylmethoxycarbonyl, methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, iso-propylsulfonyl, n-butylsulfonyl, iso- butylsulfonyl, t-butylsulfonyl, trifluoromethylsulfonyl, cyclopropylsulfonyl, Cyclobutylsulfonyl, cyclopentylsulfonyl, cyclohexylsulfonyl, arylsulfonyl, heteroarylsulfonyl, arylsulfinyl, heteroarylsulfinyl, methylsulphinyl, Ethylsulfinyl, n is propylsulfinyl, iso -propylsulfinyl, n-butylsulfinyl, iso-butylsulfinyl, t-butylsulfinyl, trifluoromethylsulfinyl, cyclopropylsulfinyl, cyclobutylsulfinyl, cyclopentylsulfinyl, cyclohexylsulfinyl, is 0, 1 or 2 R 22 are the same or different and are independently of each other
Wasserstoff, Methyl, Ethyl, n-Propyl, 1 -Methylethyl, n-Butyl, 1 -Methylpropyl, 2- Methylpropyl, 1 ,1 -Dimethylethyl, n-Pentyl, 1 -Methyl butyl, 2-Methylbutyl, 3- Methylbutyl, 1 ,1 -Dimethylpropyl, 1 ,2-Dimethylpropyl, 2,2-Dimethylpropyl, 1 - Ethylpropyl, n-Hexyl, 1 -Methylpentyl, 2-Methylpentyl, 3-Methylpentyl, 4- Methylpentyl, 1 ,1 -Dimethylbutyl, 1 ,2-Dimethylbutyl, 1 ,3-Di-methylbutyl, 2,2- Dimethylbutyl, 2,3-Dimethylbutyl, 3,3-Dimethylbutyl, 1 -Ethylbutyl, 2-Ethylbutyl, 1 ,1 ,2-Thmethylpropyl, 1 ,2,2-Thmethylpropyl, 1 -Ethyl-1 -methylpropyl und 1 - Ethyl-2-methylpropyl, Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl, Cyclohexylmethyl, Cyanomethyl, Cyanoethyl, Cyano-n-propyl, Cyano-n-butyl, Ethenyl, 1 -Propenyl, 2-Propenyl, 1 -Methyl-ethenyl, 1 -Butenyl, 2-Butenyl, 3- Butenyl, 1 -Methyl-1 -propenyl, 2-Methyl-1 -propenyl, 1 -Methyl-2-propenyl, 2- Methyl-2-propenyl, 1 -Pentenyl, 2-Pentenyl, 3-Pentenyl, 4-Pentenyl, 1 -Methyl-1 - butenyl, 2-Methyl-1 -butenyl, 3-Methyl-1 -butenyl, 1 -Methyl-2-butenyl, 2-Methyl-2 butenyl, 3-Methyl-2-butenyl, 1 -Methyl-3-butenyl, 2-Methyl-3-butenyl, 3-Methyl-3 butenyl, 1 ,1 -Dimethyl-2-propenyl, 1 ,2-Dimethyl-1 -propenyl, 1 ,2-Dimethyl-2- propenyl, 1 -Ethyl-1 -propenyl, 1 -Ethyl-2-propenyl, 1 -Hexenyl, 2-Hexenyl, 3- Hexenyl, 4-Hexenyl, 5-Hexenyl, Ethinyl, 1 -Propinyl, 2-Propinyl, 1 -Butinyl, 2- Butinyl, 3-Butinyl, 1 -Methyl-2-propinyl, 1 -Pentinyl, 2-Pentinyl, 3-Pentinyl, 4- Pentinyl, 1 -Methyl-2-butinyl, 1 -Methyl-3-butinyl, 2-Methyl-3-butinyl, 3-Methyl-1 - butinyl, 1 ,1 -Dimethyl-2-propinyl, 1 -Ethyl-2-propinyl, 2,2-Difluormethyl, 2,2,2- Trifluorethyl, 3,3,3-Trifluor-n-Propyl, Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Spiro[2.2]pent-1 -yl, Spiro[2.3]hex-1 -yl, Spiro[2.3]hex-4-yl, 3- Spiro[2.3]hex-5-yl, Spiro[3.3]hept-1 -yl, Spiro[3.3]hept-2-yl, Bicyclo[1 .1 .0]butan-1 yl, Bicyclo[1 .1 .0]butan-2-yl, Bicyclo[2.1 .0]pentan-1 -yl, Bicyclo[1 .1 .1 ]pentan-1 -yl, Bicyclo[2.1 .0]pentan-2-yl, Bicyclo[2.1 .0]pentan-5-yl, Bicyclo[2.1 .1 ]hexyl, Bicyclo[2.2.1 ]hept-2-yl, Bicyclo[2.2.2]octan-2-yl, Bicyclo[3.2.1]octan-2-yl, Bicyclo[3.2.2]nonan-2-yl, Adamantan-1 -yl, Adamantan-2-yl, 1 - Methylcyclopropyl, 2-Methylcyclopropyl, 2,2-Dimethylcyclopropyl, 2,3- Dimethylcyclopropyl, 1 ,1 '-Bi(cyclopropyl)-1 -yl, 1 ,1 '-Bi(cyclopropyl)-2-yl, 2'- Methyl-1 ,1 '-bi(cyclopropyl)-2-yl, 1 -Methylcyclobutyl, 2-Methylcyclobutyl, 3- Methylcyclobutyl, 2-Cyanocyclobutyl, 3-Cyanocyclobutyl, 3-Methoxycyclobutyl, 1 -Allylcyclopropyl, 1 -Vinylcyclobutyl, 1 -Vinylcyclopropyl, 1 -Ethylcyclopropyl, 1 - Methylcyclohexyl, 2-Methylcyclohexyl, 3-Methylcyclohexyl, 1 - Methoxycyclohexyl, 2-Methoxycyclohexyl, 3-Methoxycyclohexyl, 4- Methoxycyclohexyl, Cyclopropylnnethyl, Cyclobutylnnethyl, Cyclopentylnnethyl, Cyclohexylmethyl, Methoxymethyl, Ethoxymethyl, Ethoxyethyl, Methoxyethyl, Methoxy-n-propyl, Ethoxy-n-propyl, Methoxybutyl, Methoxy-iso-Propyl, iso- Propoxymethyl, iso-Propoxyethyl, Trifluormethoxymethyl, Trifluormethoxyethyl, Trifluormethoxy-n-propyl, Difluormethoxymethyl, Difluormethoxyethyl, Hydrogen, methyl, ethyl, n -propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1 , 1-dimethylpropyl, 1, 2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2 Dimethylbutyl, 1, 3-di-methylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2-thmethylpropyl, 1, 2,2 Trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyanomethyl, cyanoethyl, cyano-n-propyl, cyano-n-butyl, ethenyl, 1 -propenyl, 2 Propenyl, 1-methyl-ethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2 -propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-buteny 1, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, 1-dimethyl-2-propenyl, 1, 2-dimethyl-1-propenyl, 1, 2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2- Hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2- Pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2- propynyl, 1-ethyl-2-propynyl, 2,2-difluoromethyl, 2,2,2-trifluoroethyl, 3,3,3-trifluoro-n-propyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, spiro [2.2] pentane 1 -yl, spiro [2.3] hex-1-yl, spiro [2.3] hex-4-yl, 3-spiro [2.3] hex-5-yl, spiro [3.3] hept-1-yl, spiro [3.3] hept-2-yl, bicyclo [1-1, 0] butan-1-yl, bicyclo [1-1, 0] butan-2-yl, bicyclo [2.1.0] pentan-1-yl, bicyclo [1 .1 .1] pentan-1-yl, bicyclo [2.1.0] pentan-2-yl, bicyclo [2.1.0] pentan-5-yl, bicyl clo [2.1.11] hexyl, bicyclo [2.2.1] hept-2-yl, bicyclo [2.2.2] octan-2-yl, bicyclo [3.2.1] octan-2-yl, bicyclo [3.2.2] nonan-2-yl, adamantane-1-yl, adamantan-2-yl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, 2,3-dimethylcyclopropyl, 1,1'-bis (cyclopropyl) -1 - yl, 1, 1 '-Bi (cyclopropyl) -2-yl, 2'-methyl-1, 1' -bi (cyclopropyl) -2-yl, 1-methylcyclobutyl, 2-methylcyclobutyl, 3-methylcyclobutyl, 2-cyanocyclobutyl , 3-cyanocyclobutyl, 3-methoxycyclobutyl, 1-allylcyclopropyl, 1-vinylcyclobutyl, 1-vinylcyclopropyl, 1-ethylcyclopropyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 1 - Methoxycyclohexyl, 2-methoxycyclohexyl, 3-methoxycyclohexyl, 4-methoxycyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, methoxymethyl, ethoxymethyl, ethoxyethyl, methoxyethyl, methoxy-n-propyl, ethoxy-n-propyl, methoxybutyl, methoxy-iso-propyl, isopropoxymethyl, isopropoxyethyl, trifluoromethoxymethyl, trifluoromethoxyethyl, trifluoromethoxy-n-propyl, difluoromethoxymethyl, difluoromethoxyethyl,
Difluormethoxy-n-propyl, 2,2-Difluorethoxymethyl, 2,2-Difluorethoxyethyl, 2,2- Difluorethoxy-n-propyl, 2,2,2-Thfluorethoxymethyl, 2,2,2-Trifluorethoxyethyl, 2,2,2-Trifluorethoxy-n-propyl, Pentafluorethoxymethyl, Pentafluorethoxyethyl, Pentafluorethoxy-n-propyl, Methylthiomethyl, Methylthioethyl, Ethylthioethyl, Methylthio-n-propyl, Ethylthio-n-propyl, Trifluormethylthiomethyl, Difluoromethoxy-n-propyl, 2,2-difluoroethoxymethyl, 2,2-difluoroethoxyethyl, 2,2-difluoroethoxy-n-propyl, 2,2,2-thfluoroethoxymethyl, 2,2,2-trifluoroethoxyethyl, 2,2,2- Trifluoroethoxy-n-propyl, pentafluoroethoxymethyl, pentafluoroethoxyethyl, pentafluoroethoxy-n-propyl, methylthiomethyl, methylthioethyl, ethylthioethyl, methylthio-n-propyl, ethylthio-n-propyl, trifluoromethylthiomethyl,
Trifluormethylthioethyl, Trifluormethylthio-n-propyl, gegebenenfalls substituiertes Phenyl, Aryl-(Ci-C5)-alkyl, Heteroaryl, Heteroaryl-(Ci-C5)-alkyl, COR23, SO2R24, -(Ci-C6)-Alkyl-HNO2S-, (C3-C6)-Cycloalkyl-HNO2S-, Heterocyclyl, Trifluoromethylthioethyl, trifluoromethylthio-n-propyl, optionally substituted phenyl, aryl- (Ci-C 5 ) -alkyl, heteroaryl, heteroaryl- (Ci-C 5 ) -alkyl, COR 23 , SO 2 R 24 , - (Ci-C 6 ) -Alkyl-HNO 2 S-, (C 3 -C 6 ) -cycloalkyl-HNO 2 S-, heterocyclyl,
Methoxycarbonylmethyl, Ethoxycarbonylmethyl, n-Propyloxycarbonylmethyl, iso-Propyloxycarbonylmethyl, tert.-Butyloxycarbonylmethyl, Methoxycarbonylmethyl, ethoxycarbonylmethyl, n-propyloxycarbonylmethyl, isopropyloxycarbonylmethyl, tert-butyloxycarbonylmethyl,
Methoxycarbonylethyl, Ethoxycarbonylethyl, n-Propyloxycarbonylethyl, iso- Propyloxycarbonylethyl, tert.-Butyloxycarbonylethyl, Methoxycarbonyl-n-propyl, Ethoxycarbonyl-n-propyl, n-Propyloxycarbonyl-n-propyl, iso-Propyloxycarbonyl- n-propyl, tert.-Butyloxycarbonyl-n-propyl, Methoxycarbonyl, Ethoxycarbonyl, n- Propyloxycarbonyl, iso-Propyloxycarbonyl, tert.Butyloxycarbonyl, Aryl-(Ci-Cs)- Alkoxycarbonyl-(Ci-C5)-alkyl, Aryl-(Ci-C5)-Alkoxycarbonyl, Heteroaryl-(Ci-C5)- Alkoxycarbonyl, Allyloxycarbonyl, Propargyloxycarbonyl, Heterocyclyl-(Ci-C5)- alkyl stehen für Wasserstoff, Methyl, Ethyl, n-Propyl, 1 -Methylethyl, n-Butyl, 1 -Methylpropyl, 2-Methylpropyl, 1 ,1 -Dimethylethyl, n-Pentyl, 1 -Methylbutyl, 2-Methylbutyl, 3- Methylbutyl, 1 ,1 -Dimethylpropyl, 1 ,2-Dimethylpropyl, 2,2-Dimethylpropyl, 1 - Ethylpropyl, n-Hexyl, 1 -Methylpentyl, 2-Methylpentyl, 3-Methylpentyl, 4- Methylpentyl, 1 ,1 -Dimethylbutyl, 1 ,2-Dimethylbutyl, 1 ,3-Di-methylbutyl, 2,2- Dimethylbutyl, 2,3-Dimethylbutyl, 3,3-Dimethylbutyl, 1 -Ethylbutyl, 2-Ethylbutyl, 1 ,1 ,2-Thmethylpropyl, 1 ,2,2-Thmethylpropyl, 1 -Ethyl-1 -methylpropyl und 1 - Ethyl-2-methylpropyl, Cyclopropylnnethyl, Cyclobutylnnethyl, Cyclopentylnnethyl, Cyclohexylmethyl, Cyanomethyl, Cyanoethyl, Cyano-n-propyl, Cyano-n-butyl, Ethenyl, 1 -Propenyl, 2-Propenyl, 1 -Methyl-ethenyl, 1 -Butenyl, 2-Butenyl, 3- Butenyl, 1 -Methyl-1 -propenyl, 2-Methyl-1 -propenyl, 1 -Methyl-2-propenyl, 2- Methyl-2-propenyl, 1 -Pentenyl, 2-Pentenyl, 3-Pentenyl, 4-Pentenyl, 1 -Methyl-1 - butenyl, 2-Methyl-1 -butenyl, 3-Methyl-1 -butenyl, 1 -Methyl-2-butenyl, 2-Methyl-2- butenyl, 3-Methyl-2-butenyl, 1 -Methyl-3-butenyl, 2-Methyl-3-butenyl, 3-Methyl-3- butenyl, 1 ,1 -Dimethyl-2-propenyl, 1 ,2-Dimethyl-l -propenyl, 1 ,2-Dimethyl-2- propenyl, 1 -Ethyl-1 -propenyl, 1 -Ethyl-2-propenyl, 1 -Hexenyl, 2-Hexenyl, 3- Hexenyl, 4-Hexenyl, 5-Hexenyl, 1 -Methyl-1 -pentenyl, 2-Methyl-1 -pentenyl, 3- Methyl-1 -pentenyl, 4-Methyl-1 -pentenyl, 1 -Methyl-2-pentenyl, 2-Methyl-2- pentenyl, 3-Methyl-2-pentenyl, 4-Methyl-2-pentenyl, 1 -Methyl-3-pentenyl, 2- Methyl-3-pentenyl, 3-Methyl-3-pentenyl, 4-Methyl-3-pentenyl, 1 -Methyl-4- pentenyl, 2-Methyl-4-pentenyl, 3-Methyl-4-pentenyl, 4-Methyl-4-pentenyl, 1 ,1 - Dimethyl-2-butenyl, 1 ,1 -Dimethyl-3-butenyl, 1 ,2-Dimethyl-1 -butenyl, 1 ,2- Dimethyl-2-butenyl, 1 ,2-Dimethyl-3-butenyl, 1 ,3-Dimethyl-1 -butenyl, 1 ,3- Dimethyl-2-butenyl, 1 ,3-Dimethyl-3-butenyl, 2,2-Dimethyl-3-butenyl, 2,3- Dimethyl-1 -butenyl, 2,3-Dimethyl-2-butenyl, 2,3-Dimethyl-3-butenyl, 3,3- Dimethyl-1 -butenyl, 3,3-Dimethyl-2-butenyl, 1 -Ethyl-1 -butenyl, 1 -Ethyl-2-butenyl,Methoxycarbonylethyl, ethoxycarbonylethyl, n-propyloxycarbonylethyl, isopropyloxycarbonylethyl, tert-butyloxycarbonylethyl, methoxycarbonyl-n-propyl, ethoxycarbonyl-n-propyl, n-propyloxycarbonyl-n-propyl, isopropyloxycarbonyl-n-propyl, tert-butyloxycarbonyl- n-propyl, methoxycarbonyl, ethoxycarbonyl, n-propyloxycarbonyl, isopropyloxycarbonyl, tert-butyloxycarbonyl, aryl- (C 1 -C 5) -alkoxycarbonyl- (C 1 -C 5) -alkyl, aryl- (C 1 -C 5) -alkoxycarbonyl, heteroaryl- (C 1 -C 5) -alkoxycarbonyl, allyloxycarbonyl, propargyloxycarbonyl, heterocyclyl- (C 1 -C 5) -alkyl stand for hydrogen, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1 , 1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl , 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-di-methylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-di methylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2-thmethylpropyl, 1, 2,2-thmethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, Cyanomethyl, cyanoethyl, cyano-n-propyl, cyano-n-butyl, Ethenyl, 1-propenyl, 2-propenyl, 1-methyl-ethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2- propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, 1-dimethyl-2-propenyl, 1, 2-dimethyl-1-propenyl, 1, 2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2- Hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl 2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3 pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1, 1-dimethyl-2 butenyl, 1, 1-dimethyl-3-butenyl, 1, 2-Dimethyl-1-butenyl, 1, 2-dimethyl-2-butenyl, 1, 2-dimethyl-3-butenyl, 1, 3-dimethyl-1-butenyl, 1, 3-dimethyl-2-butenyl, 1, 3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3, 3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl,
1 - Ethyl-3-butenyl, 2-Ethyl-1 -butenyl, 2-Ethyl-2-butenyl, 2-Ethyl-3-butenyl, 1 ,1 ,2- Trinnethyl-2-propenyl, 1 -Ethyl-1 -methyl-2-propenyl, 1 -Ethyl-2-methyl-1 -propenyl und 1 -Ethyl-2-methyl-2-propenyl, Ethinyl, 1 -Propinyl, 2-Propinyl, 1 -Butinyl, 2- Butinyl, 3-Butinyl, 1 -Methyl-2-propinyl, 1 -Pentinyl, 2-Pentinyl, 3-Pentinyl, 4- Pentinyl, 1 -Methyl-2-butinyl, 1 -Methyl-3-butinyl, 2-Methyl-3-butinyl, 3-Methyl-1 - butinyl, 1 ,1 -Dimethyl-2-propinyl, 1 -Ethyl-2-propinyl, 1 -Hexinyl, 2-Hexinyl, 3- Hexinyl, 4-Hexinyl, 5-Hexinyl, 1 -Methyl-2-pentinyl, 1 -Methyl-3-pentinyl, 1 - Methyl-4-pentinyl, 2-Methyl-3-pentinyl, 2-Methyl-4-pentinyl, 3-Methyl-1 -pentinyl, 3-Methyl-4-pentinyl, 4-Methyl-1 -pentinyl, 4-Methyl-2-pentinyl, 1 ,1 -Dimethyl-2- butinyl, 1 ,1 -Dimethyl-3-butinyl, 1 ,2-Dimethyl-3-butinyl, 2,2-Dimethyl-3-butinyl, 3,3-Dimethyl-1 -butinyl, 1 -Ethyl-2-butinyl, 1 -Ethyl-3-butinyl, 2-Ethyl-3-butinyl, 1 - Ethyl-1 -methyl-2-propinyl, Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, , Adamantan-1 -yl, Adamantan-2-yl, 1 -Methylcyclopropyl, 2-Methylcyclopropyl, 2,2-Dimethylcyclopropyl, 2,3-Dimethylcyclopropyl, 1 -Methylcyclobutyl, 2- Methylcyclobutyl, 3-Methylcyclobutyl, 2-Cyanocyclobutyl, 3-Cyanocyclobutyl, 3- Methoxycyclobutyl, 1 -AI lyl cyclopropyl, 1 -Ethylcyclopropyl, 1 -Methylcyclohexyl,1 - ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1, 1, 2-trinethyl-2-propenyl, 1-ethyl-1 - methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3- Butinyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl 2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4 pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2, 2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methyl 2-propynyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, Adamantane-1-yl, adamantan-2-yl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, 2,3-dimethylcyclopropyl, 1-methylcyclobutyl, 2-methylcyclobutyl, 3-methylcyclobutyl, 2-cyanocyclobutyl, 3 Cyanocyclobutyl, 3-methoxycyclobutyl, 1-alkylcyclopropyl, 1-ethylcyclopropyl, 1-methylcyclohexyl,
2- Methylcyclohexyl, 3-Methylcyclohexyl, 2-Methoxycyclohexyl, 3- Methoxycyclohexyl, 4-Methoxycyclohexyl, Cyclopropylnnethyl, Cyclobutylnnethyl Cyclopentylmethyl, Cyclohexylmethyl, Trifluormethyl, Pentafluorethyl, 1 ,1 ,2,2- Tetrafluorethyl, Heptafluorpropyl, Nonafluorbutyl, Chlordifluormethyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 2-methoxycyclohexyl, 3 Methoxycyclohexyl, 4-methoxycyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, trifluoromethyl, pentafluoroethyl, 1,1,2,2-tetrafluoroethyl, heptafluoropropyl, nonafluorobutyl, chlorodifluoromethyl,
Bromdifluormethyl, Dichlorfluormethyl, loddifluormethyl, Bromfluormethyl, 1 - Fluorethyl, 2-Fluorethyl, Fluormethyl, Difluormethyl, 2,2-Difluorethyl, 2,2,2- Trifluorethyl, 3,3,3-Trifluor-n-propyl, Methoxymethyl, Ethoxymethyl, Ethoxyethyl Methoxyethyl, Methoxy-n-propyl, Ethoxy-n-propyl, Methoxybutyl, Methoxy-iso- Propyl, iso-Propoxymethyl, iso-Propoxyethyl, gegebenenfalls substituiertes Phenyl, Aryl-(Ci-C6)-alkyl, Heteroaryl, Heteroaryl-(Ci-C6)-alkyl, Bromodifluoromethyl, dichlorofluoromethyl, iododifluoromethyl, bromofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, fluoromethyl, difluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 3,3,3-trifluoro-n-propyl, methoxymethyl, ethoxymethyl, Ethoxyethyl methoxyethyl, methoxy-n-propyl, ethoxy-n-propyl, methoxybutyl, methoxy-iso-propyl, iso-propoxymethyl, isopropoxyethyl, optionally substituted phenyl, aryl- (C 1 -C 6 ) -alkyl, heteroaryl, heteroaryl (C 1 -C 6 ) -alkyl,
Methoxycarbonylmethyl, Ethoxycarbonylmethyl, n-Propyloxycarbonylmethyl, iso-Propyloxycarbonylmethyl, tert.-Butyloxycarbonylmethyl, Methoxycarbonylmethyl, ethoxycarbonylmethyl, n-propyloxycarbonylmethyl, isopropyloxycarbonylmethyl, tert-butyloxycarbonylmethyl,
Methoxycarbonylethyl, Ethoxycarbonylethyl, n-Propyloxycarbonylethyl, iso- Propyloxycarbonylethyl, tert.-Butyloxycarbonylethyl, Methoxycarbonyl-n-propyl, Ethoxycarbonyl-n-propyl, n-Propyloxycarbonyl-n-propyl, iso-Propyloxycarbonyl- n-propyl, tert.-Butyloxycarbonyl-n-propyl, Allyloxycarbonylmethyl, Methoxycarbonylethyl, ethoxycarbonylethyl, n-propyloxycarbonylethyl, isopropyloxycarbonylethyl, tert-butyloxycarbonylethyl, methoxycarbonyl-n-propyl, ethoxycarbonyl-n-propyl, n-propyloxycarbonyl-n-propyl, isopropyloxycarbonyl-n-propyl, tert-butyloxycarbonyl- n-propyl, allyloxycarbonylmethyl,
Allyloxycarbonylethyl, Allyloxycarbonyl-n-propyl, Aryl-(Ci-C6)-Alkoxycarbonyl- (Ci-C6)-alkyl, Hydroxycarbonyl-(Ci-C6)-alkyl, Heterocyclyl, Heterocyclyl-(Ci-C6) alkyl steht und für Wasserstoff, Methyl, Ethyl, n-Propyl, 1 -Methylethyl, n-Butyl, 1 -Methylpropyl, 2-Methylpropyl, 1 ,1 -Dimethylethyl, n-Pentyl, 1 -Methylbutyl, 2-Methylbutyl, 3- Methylbutyl, 1 ,1 -Dimethylpropyl, 1 ,2-Dimethylpropyl, 2,2-Dimethylpropyl, 1 - Ethylpropyl, n-Hexyl, 1 -Methylpentyl, 2-Methylpentyl, 3-Methylpentyl, 4- Methylpentyl, 1 ,1 -Dimethylbutyl, 1 ,2-Dimethylbutyl, 1 ,3-Di-methylbutyl, 2,2- Dimethylbutyl, 2,3-Dimethylbutyl, 3,3-Dimethylbutyl, 1 -Ethylbutyl, 2-Ethylbutyl, 1 ,1 ,2-Trimethylpropyl, 1 ,2,2-Trimethylpropyl, 1 -Ethyl-1 -methylpropyl und 1 - Ethyl-2-methylpropyl, Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl, Cyclohexylmethyl, Cyanomethyl, Cyanoethyl, Cyano-n-propyl, Cyano-n-butyl, Ethenyl, 1 -Propenyl, 2-Propenyl, 1 -Methyl-ethenyl, 1 -Butenyl, 2-Butenyl, 3- Butenyl, 1 -Methyl-1 -propenyl, 2-Methyl-1 -propenyl, 1 -Methyl-2-propenyl, 2- Methyl-2-propenyl, 1 -Pentenyl, 2-Pentenyl, 3-Pentenyl, 4-Pentenyl, 1 -Methyl-1 - butenyl, 2-Methyl-1 -butenyl, 3-Methyl-1 -butenyl, 1 -Methyl-2-butenyl, 2-Methyl-2 butenyl, 3-Methyl-2-butenyl, 1 -Methyl-3-butenyl, 2-Methyl-3-butenyl, 3-Methyl-3 butenyl, 1 ,1 -Dimethyl-2-propenyl, 1 ,2-Dimethyl-1 -propenyl, 1 ,2-Dimethyl-2- propenyl, 1 -Ethyl-1 -propenyl, 1 -Ethyl-2-propenyl, 1 -Hexenyl, 2-Hexenyl, 3- Hexenyl, 4-Hexenyl, 5-Hexenyl, Ethinyl, 1 -Propinyl, 2-Propinyl, 1 -Butinyl, 2- Butinyl, 3-Butinyl, 1 -Methyl-2-propinyl, Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Adamantan-1 -yl, Adamantan-2-yl, 1 -Methylcyclopropyl, 2- Methylcyclopropyl, 2,2-Dimethylcyclopropyl, 2,3-Dimethylcyclopropyl, 1 ,1 '- Bi(cyclopropyl)-1 -yl, 1 ,1 '-Bi(cyclopropyl)-2-yl, 2'-Methyl-1 ,1 '-bi(cyclopropyl)-2-yl, Cyclopropylmethyl, Cyclobutyl methyl, Cyclopentylmethyl, Cyclohexylmethyl, Trifluormethyl, Pentafluorethyl, 1 ,1 ,2,2-Tetrafluorethyl, Heptafluorpropyl, Nonafluorbutyl, 1 -Fluorethyl, 2-Fluorethyl, Fluormethyl, Difluormethyl, 2,2- Difluorethyl, 2,2,2-Trifluorethyl, 3,3,3-Trifluor-n-propyl, Difluor-tert.-butyl, Methoxymethyl, Ethoxymethyl, Ethoxyethyl, Methoxyethyl, Methoxy-n-propyl, Ethoxy-n-propyl, Methoxybutyl, Methoxy-iso-Propyl, iso-Propoxymethyl, iso- Propoxyethyl, gegebenenfalls substituiertes Phenyl, Aryl-(Ci-C6)-alkyl, Allyloxycarbonylethyl, allyloxycarbonyl-n-propyl, aryl- (Ci-C6) -alkoxycarbonyl- (Ci-C6) -alkyl, hydroxycarbonyl- (Ci-C6) -alkyl, heterocyclyl, heterocyclyl- (Ci-C6) alkyl and represents hydrogen , Methyl, ethyl, n -propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1, 1 -Dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl , 1, 3-Di-methylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2-trimethylpropyl, 1, 2,2-trimethylpropyl , 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyanomethyl, cyanoethyl, cyano-n-propyl, cyano-n-butyl, ethenyl, 1-propenyl, 2-propenyl , 1-methyl-ethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propene yl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl 3-butenyl, 3-methyl-3-butenyl, 1, 1-dimethyl-2-propenyl, 1, 2-dimethyl-1-propenyl, 1, 2-dimethyl-2- propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, ethynyl, 1-propynyl, 2-propynyl, 1 - Butinyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantan-1-yl, adamantan-2-yl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2- Dimethylcyclopropyl, 2,3-dimethylcyclopropyl, 1,1'-bi (cyclopropyl) -1-yl, 1,1 '-Bi (cyclopropyl) -2-yl, 2'-methyl-1,1' -bi (cyclopropyl) 2-yl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, trifluoromethyl, pentafluoroethyl, 1,1,2,2-tetrafluoroethyl, heptafluoropropyl, nonafluorobutyl, 1-fluoroethyl, 2-fluoroethyl, fluoromethyl, difluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 3,3,3-trifluoro-n-propyl, difluoro-tert-butyl, methoxymethyl, ethoxymethyl, ethoxyethyl, methoxyethyl, methoxy-n-propyl, ethoxy-n-propyl, methoxybutyl, methoxy -iso-propyl, iso-propoxymethyl, iso -propoxyethyl, optionally substituted phenyl, aryl- (Ci-C 6) alkyl,
Heteroaryl, Heteroaryl-(Ci-C6)-alkyl, Heterocyclyl-(Ci-C6)-alkyl, NR21R22 steht. z Speziellen bevorzugt sind Verbindungen der allgemeinen Formel (I), die durchmeln (la) bis (ly) beschrieben werden, Heteroaryl, heteroaryl- (C 1 -C 6 ) -alkyl, heterocyclyl- (C 1 -C 6 ) -alkyl, NR 21 R 22 . Particular preference is given to compounds of the general formula (I) which are described by (la) to (ly)
worin R1, R2 und R7 unabhängig voneinander für Wasserstoff, Fluor, Chlor, Brom, lod, Cyano, Nitro, Thiocyanato, Isothiocyanato, Methoxy, Ethoxy, iso-Propyloxy, Methylsulfonyl, Hydrothio, Hydroxy, Amino, Imino, Diazo, Methyl, Ethyl, n- Propyl, 1 -Methylethyl, n-Butyl, 1 -Methylpropyl, tert.-Butyl, Cyclopropylmethyl, Cyclopropyl, Cyclobutyl, Cyclopentyl, Ethenyl, 1 -Propenyl, 2-Propenyl, 1 -Methyl- ethenyl, Methoxymethyl, Trifluormethyl, Pentafluorethyl, Chlordifluormethyl, Difluormethyl, 2,2-Difluorethyl, 2,2,2-Trifluorethyl, Trifluormethoxy, 2,2,2- Trifluorethoxy, Difluormethoxy, Trifluormethylthio, Methylthio, Ethylthio, Phenyl, Pyridin-2-yl, Pyridin-3-yl, Pyridin-4-yl, tert.Butyloxycarbonylamino, wherein R 1 , R 2 and R 7 are independently hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, thiocyanato, isothiocyanato, methoxy, ethoxy, iso-propyloxy, methylsulfonyl, hydrothio, hydroxy, amino, imino, diazo, methyl , Ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, tert-butyl, cyclopropylmethyl, cyclopropyl, cyclobutyl, cyclopentyl, ethenyl, 1-propenyl, 2-propenyl, 1-methyl-ethenyl, methoxymethyl, Trifluoromethyl, pentafluoroethyl, chlorodifluoromethyl, difluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, trifluoromethoxy, 2,2,2-trifluoroethoxy, difluoromethoxy, trifluoromethylthio, methylthio, ethylthio, phenyl, pyridin-2-yl, pyridine 3-yl, pyridin-4-yl, tert-butyloxycarbonylamino,
Dimethylamino, Hydroxycarbonyl, Methoxycarbonyl, Ethoxycarbonyl stehen,  Dimethylamino, hydroxycarbonyl, methoxycarbonyl, ethoxycarbonyl,
X1, X2 und X3 gleich oder verschieden sind und unabhängig voneinander für O X 1 , X 2 and X 3 are the same or different and are each independently O.
(Sauerstoff), S (Schwefel), N (Stickstoff), die Gruppierung C-R2 oder die (Oxygen), S (sulfur), N (nitrogen), the group CR 2 or the
Gruppierung N-R20 stehen, wobei jedoch in keinem Fall ein O- und S-Atom benachbart sind und wobei in keinem Fall jeweils mehr als ein O- oder S-Atom im gebildeten 5-gliedrigen Ring enthalten ist, und wobei R2 in der Gruppierung C-R2 und R20 in der Gruppierung N-R20 jeweils gleiche oder verschiedene Bedeutungen gemäß der oben- oder nachstehenden Definitionen haben, W für O (Sauerstoff) oder S (Schwefel) steht, Grouping NR 20 are, but in no case adjacent to an O and S atom and in each case in each case more than one O or S atom in the formed 5-membered ring is contained, and wherein R 2 in the grouping CR 2 and R 20 in the moiety NR 20 each have the same or different meanings according to the above or below definitions, W is O (oxygen) or S (sulfur),
A1, A2, A3, A4 und A5 gleich oder verschieden sind und unabhängig voneinander für N (Stickstoff) oder die Gruppierung C-R7 stehen, wobei jedoch in keinem Fall mehr als zwei N-Atome benachbart sind, und wobei R7 in der Gruppierung C-R7 jeweils gleiche oder verschiedene Bedeutungen gemäß der oben stehendenA 1 , A 2 , A 3 , A 4 and A 5 are the same or different and are independently N (nitrogen) or the group CR 7 , but in no case more than two N atoms are adjacent, and wherein R 7 in the group CR 7 each have the same or different meanings according to the above
Definition hat, Definition has,
R5 und R6 unabhängig voneinander für Wasserstoff, Methyl, Ethyl, n-Propyl, 1 -R 5 and R 6 independently of one another represent hydrogen, methyl, ethyl, n-propyl, 1 -
Methylethyl, n-Butyl, Cyclopropylmethyl, Cyclopropyl, Cyclobutyl, Cyclopentyl, Methoxycarbonyl, Ethoxycarbonyl, Hydroxycarbonyl, Methoxycarbonylmethyl,Methylethyl, n-butyl, cyclopropylmethyl, cyclopropyl, cyclobutyl, cyclopentyl, methoxycarbonyl, ethoxycarbonyl, hydroxycarbonyl, methoxycarbonylmethyl,
Ethoxycarbonylmethyl stehen, Ethoxycarbonylmethyl stand,
R1 und X1, wenn X1 für eine Gruppe C-R2 steht, mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden, und X2, wenn beide für eine Gruppe C-R2 stehen, mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden, und A2, wenn beide für eine Gruppe C-R7 stehen, mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden, und A3, wenn beide für eine Gruppe C-R7 stehen, mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden und und A4, wenn beide für eine Gruppe C-R7 stehen, mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden, R 1 and X 1 , when X 1 is a group CR 2 , with the atoms to which they are attached, a fully saturated, partially saturated or completely form unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring, and X 2 , when both represent a group CR 2 , with the atoms to which they are attached, a fully saturated, partially saturated or fully unsaturated, form optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring, and A 2 , when both represent a group CR 7 , with the atoms to which they are attached, a fully saturated, partially saturated or fully unsaturated, optionally Heteroatoms form interrupted and optionally further substituted 5-7 membered ring, and A 3 , when both represent a group CR 7 , with the atoms to which they are attached, a fully saturated, partially saturated or fully unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered n ring and A 4 , when both represent a group CR 7 , with the atoms to which they are attached, a fully saturated, partially saturated or fully unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring form,
Y für eine Bindung oder für die Gruppierungen Y-1 bis Y-2 Y is a bond or groups Y-1 to Y-2
Y-1 Y-2 steht, wobei R8, R9, R10, R1 1, R12, R13 jeweils die Bedeutung gemäß der Y-1 Y-2, wherein R 8 , R 9 , R 10 , R 1 1 , R 12 , R 13 each have the meaning according to the
nachstehenden Definition haben und wobei der Pfeil für eine Bindung zum 6- gliedrigen Ring mit den Gruppierungen A1, A2, A3, A4 und A5 steht und R8, R9, R10, R1 1, R12 und R13 unabhängig voneinander für Wasserstoff, Methyl stehen, have the following definition and wherein the arrow stands for a bond to the 6-membered ring with the groupings A 1 , A 2 , A 3 , A 4 and A 5 and R 8, R 9, R 10, R 1 1, R 12 and R 13 are independently hydrogen, methyl,
R5 und R6 mit dem Atom, an das sie gebunden sind, einen vollständig gesättigten, oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden und R 5 and R 6 with the atom to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring, and
R20 für Wasserstoff, Methyl, Ethyl, n-Propyl, 1 -Methylethyl, n-Butyl, 1 -Methylpropyl, 2-Methylpropyl, Cyclopropylmethyl, Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Heterocyclyl, Methylcarbonyl, Ethylcarbonyl, iso-Propylcarbonyl, iso-Butylcarbonyl, tert.-Butylcarbonyl, Cyclopropylcarbonyl, Cyclobutylcarbonyl, Cyclopentylcarbonyl, Cyclohexylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl, tert.-Butyloxycarbonyl steht, R 20 is hydrogen, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, cyclopropylmethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, heterocyclyl, methylcarbonyl, ethylcarbonyl, iso -propylcarbonyl, iso Butylcarbonyl, tert-butylcarbonyl, cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl, methoxycarbonyl, ethoxycarbonyl, tert-butyloxycarbonyl,
Die oben aufgeführten allgemeinen oder in Vorzugsbereichen aufgeführten The general or preferred ones listed above
Restedefinitionen gelten sowohl für die Endprodukte der allgemeinen Formel (I) als auch entsprechend für die jeweils zur Herstellung benötigten Ausgangs- oder Residue definitions apply both to the end products of the general formula (I) and correspondingly to the starting material or preparation required in each case for the preparation
Zwischenprodukte. Diese Restedefinitionen können untereinander, also auch zwischen den angegebenen bevorzugten Bereichen beliebig kombiniert werden. Intermediates. These remainder definitions can be combined with one another as desired, ie also between the specified preferred ranges.
Im Hinblick auf die erfindungsgemäßen Verbindungen werden die vorstehend und weiter unten verwendeten Bezeichnungen erläutert. Diese sind dem Fachmann geläufig und haben insbesondere die im Folgenden erläuterten Bedeutungen: With regard to the compounds according to the invention, the terms used above and below are explained. These are familiar to the person skilled in the art and in particular have the meanings explained below:
Erfindungsgemäß steht "Arylsulfonyl" für gegebenenfalls substituiertes Phenylsulfonyl oder gegebenenfalls substituiertes polycyclisches Arylsulfonyl, hier insbesondere gegebenenfalls substituiertes Naphthyl-sulfonyl, beispielsweise substituiert durch Fluor, Chlor, Brom, lod, Cyano, Nitro, Alkyl-, Haloalkyl-, Haloalkoxy-, Amino-, According to the invention "arylsulfonyl" is optionally substituted phenylsulfonyl or optionally substituted polycyclic arylsulfonyl, here in particular optionally substituted naphthylsulfonyl, for example substituted by fluorine, chlorine, bromine, iodine, cyano, nitro, alkyl, haloalkyl, haloalkoxy, amino,
Alkylamino-, Alkylcarbonylamino-, Dialkylamino- oder Alkoxy-gruppen. Erfindungsgemäß steht "Cycloalkylsulfonyl" - in Alleinstellung oder als Bestandteil einer chemischen Gruppe - für gegebenenfalls substituiertes Cycloalkylsulfonyl, vorzugsweise mit 3 bis 6 Kohlenstoffatomen wie beispielsweise Cyclopropylsulfonyl, Cyclobutylsulfonyl, Cyclopentylsulfonyl oder Cyclohexylsulfonyl. Erfindungsgemäß steht "AI kylsulfonyl" - in Alleinstellung oder als Bestandteil einer chemischen Gruppe - für geradkettiges oder verzweigtes Alkylsulfonyl, vorzugsweise mit 1 bis 8, oder mit 1 bis 6 Kohlenstoffatomen, z.B. (aber nicht beschränkt auf) (Ci- C6)-Alkylsulfonyl wie Methylsulfonyl, Ethylsulfonyl, Propylsulfonyl, 1 -Methylethyl- sulfonyl, Butylsulfonyl, 1 -Methylpropylsulfonyl, 2-Methylpropylsulfonyl, 1 ,1 -Dimethyl- ethylsulfonyl, Pentylsulfonyl, 1 -Methylbutylsulfonyl, 2-Methylbutylsulfonyl, 3-Methyl- butylsulfonyl, 1 ,1 -Dimethylpropylsulfonyl, 1 ,2-Dimethylpropylsulfonyl, 2,2-Dimethyl- propylsulfonyl, 1 -Ethylpropylsulfonyl, Hexylsulfonyl, 1 -Methylpentylsulfonyl, 2-Methyl- pentylsulfonyl, 3-Methylpentylsulfonyl, 4-Methylpentylsulfonyl, 1 ,1 -Dimethylbutyl- sulfonyl, 1 ,2-Dimethylbutylsulfonyl, 1 ,3-Dimethylbutylsulfonyl, 2,2-Dimethylbutyl- sulfonyl, 2,3-Dimethylbutylsulfonyl, 3,3-Dimethylbutylsulfonyl, 1 -Ethylbutylsulfonyl, 2- Ethylbutylsulfonyl, 1 ,1 ,2-Trimethylpropylsulfonyl, 1 ,2,2-Trimethylpropylsulfonyl, 1 -Ethyl- 1 -methylpropylsulfonyl und 1 -Ethyl-2-methylpropylsulfonyl. Erfindungsgemäß steht "Heteroarylsulfonyl" für gegebenenfalls substituiertes Alkylamino, alkylcarbonylamino, dialkylamino or alkoxy groups. According to the invention "cycloalkylsulfonyl" - alone or as part of a chemical group - is optionally substituted Cycloalkylsulfonyl, preferably having 3 to 6 carbon atoms such as cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl or cyclohexylsulfonyl. According to the invention "AI kylsulfonyl" - alone or as part of a chemical group - is straight-chain or branched alkylsulfonyl, preferably having 1 to 8, or having 1 to 6 carbon atoms, for example (but not limited to) (Ci- C6) alkylsulfonyl as Methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, 1,1-dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methyl-butylsulfonyl, 1, 1 Dimethylpropylsulphonyl, 1, 2-dimethylpropylsulphonyl, 2,2-dimethylpropylsulphonyl, 1-ethylpropylsulphonyl, hexylsulphonyl, 1-methylpentylsulphonyl, 2-methylpentylsulphonyl, 3-methylpentylsulphonyl, 4-methylpentylsulphonyl, 1,1-dimethylbutylsulfonyl, 1, 2-dimethylbutylsulfonyl, 1, 3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1, 1, 2-trimethylprop ylsulfonyl, 1, 2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl and 1-ethyl-2-methylpropylsulfonyl. According to the invention "heteroarylsulfonyl" is optionally substituted
Pyridylsulfonyl, Pyrimidinylsulfonyl, Pyrazinylsulfonyl oder gegebenenfalls Pyridylsulfonyl, pyrimidinylsulfonyl, pyrazinylsulfonyl or optionally
substituiertes polycyclisches Heteroarylsulfonyl, hier insbesondere gegebenenfalls substituiertes Chinolinylsulfonyl, beispielsweise substituiert durch Fluor, Chlor, Brom, lod, Cyano, Nitro, Alkyl-, Haloalkyl-, Haloalkoxy-, Amino-, Alkylamino-, substituted polycyclic heteroarylsulfonyl, here in particular optionally substituted quinolinylsulfonyl, for example substituted by fluorine, chlorine, bromine, iodine, cyano, nitro, alkyl, haloalkyl, haloalkoxy, amino, alkylamino,
Alkylcarbonylamino-, Dialkylamino- oder Alkoxygruppen. Alkylcarbonylamino, dialkylamino or alkoxy groups.
Erfindungsgemäß steht "Alkylthio" - in Alleinstellung oder als Bestandteil einer chemischen Gruppe - für geradkettiges oder verzweigtes S-Alkyl, vorzugsweise mit 1 bis 8, oder mit 1 bis 6 Kohlenstoffatomen, wie (C1-C10)-, (C1-C6)- oder (Ci-C4)-Alkylthio, z.B. (aber nicht beschränkt auf) (Ci-C6)-Alkylthio wie Methylthio, Ethylthio, Propylthio, 1 -Methylethylthio, Butylthio, 1 -Methylpropylthio, 2-Methylpropylthio, 1 ,1 -Dimethylethyl- thio, Pentylthio, 1 -Methylbutylthio, 2-Methylbutylthio, 3-Methylbutylthio, 1 ,1 -Dimethyl- propylthio, 1 ,2-Dimethylpropylthio, 2,2-Dimethylpropylthio, 1 -Ethylpropylthio, Hexylthio,According to the invention, "alkylthio" - alone or as part of a chemical group - represents straight-chain or branched S-alkyl, preferably having 1 to 8, or having 1 to 6 carbon atoms, such as (C 1 -C 10) -, (C 1 -C 6) - or (C 1 -C 4 ) -alkylthio, for example (but not limited to) (C 1 -C 6) -alkylthio, such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1, 1-dimethylethyl thio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1, 1-dimethylpropylthio, 1, 2-dimethylpropylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio,
1 - Methylpentylthio, 2-Methylpentylthio, 3-Methylpentylthio, 4-Methylpentylthio, 1 ,1 -Di- methylbutylthio, 1 ,2-Dimethylbutylthio, 1 ,3-Dimethylbutylthio, 2,2-Dimethylbutylthio,1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1, 1-dimethylbutylthio, 1, 2-dimethylbutylthio, 1, 3-dimethylbutylthio, 2,2-dimethylbutylthio,
2,3-Dimethylbutylthio, 3,3-Dimethylbutylthio, 1 -Ethylbutylthio, 2-Ethylbutylthio, 1 ,1 ,2- Trimethylpropylthio, 1 ,2,2-Trimethylpropylthio, 1 -Ethyl-1 -methylpropylthio und 1 -Ethyl-2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1, 1, 2-trimethylpropylthio, 1, 2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and 1-ethyl
2- methylpropylthio. Alkenylthio bedeutet erfindungsgemäßt ein über ein Schwefelatom gebundenen Alkenylrest, Alkinylthio bedeutet ein über ein Schwefelatom gebundenen Alkinylrest, Cycloalkylthio bedeutet ein über ein Schwefelatom gebundenen Cycloalkylrest und Cycloalkenylthio bedeutet ein über ein Schwefelatom gebundenen Cycloalkenylrest. 2-methylpropylthio. According to the invention, alkenylthio means an alkenyl radical bonded via a sulfur atom, alkynylthio means an alkynyl radical bonded via a sulfur atom, cycloalkylthio means a cycloalkyl radical bonded via a sulfur atom, and cycloalkenylthio means a cycloalkenyl radical bonded via a sulfur atom.
Alkylsulfinyl (Alkyl-S(=O)-), soweit nicht an anderer Stelle anders definiert steht erfindungsgemäß für Alkylreste, die über -S(=O)- an das Gerüst gebunden sind, wie (C1-C10)-, (Ci-C6)- oder (Ci-C4)-Al kylsulfinyl, z. B. (aber nicht beschränkt auf) (C1- C6)-Alkylsulfinyl wie Methylsulfinyl, Ethylsulfinyl, Propylsulfinyl, 1 -Methylethylsulfinyl, Butylsulfinyl, 1 -Methylpropylsulfinyl, 2-Methylpropylsulfinyl, 1 ,1 -Dimethylethylsulfinyl, Pentylsulfinyl, 1 -Methylbutylsulfinyl, 2-Methylbutylsulfinyl, 3-Methylbutylsulfinyl, 1 ,1 - Dimethylpropylsulfinyl, 1 ,2-Dimethylpropylsulfinyl, 2,2-Dimethylpropylsulfinyl, 1 -Ethyl- propylsulfinyl, Hexylsulfinyl, 1 -Methylpentylsulfinyl, 2-Methylpentylsulfinyl, 3-Methyl- pentylsulfinyl, 4-Methylpentylsulfinyl, 1 ,1 -Dimethylbutylsulfinyl, 1 ,2-Dimethylbutyl- sulfinyl, 1 ,3-Dimethylbutylsulfinyl, 2,2-Dimethylbutylsulfinyl, 2,3-Dimethylbutylsulfinyl, 3,3-Dimethylbutylsulfinyl, 1 -Ethylbutylsulfinyl, 2-Ethylbutylsulfinyl, 1 ,1 ,2-Trimethyl- propylsulfinyl, 1 ,2,2-Trimethylpropylsulfinyl, 1 -Ethyl-1 -methylpropylsulfinyl und 1 -Ethyl- 2-methylpropylsulfinyl. Analog sind Alkenylsulfinyl und Alkinylsulfinyl, erfindungsgemäß definiert als Alkenyl- bzw. Alkinylreste, die über -S(=O)- an das Gerüst gebunden sind, wie (C2-C10)-, (C2- C6)- oder (C2-C )-Alkenylsulfinyl bzw. (C3-C10)-, (C3-C6)- oder (C3-C4)-Al kinylsulfinyl . Alkylsulfinyl (alkyl-S (= O) -), unless otherwise defined elsewhere, according to the invention represents alkyl radicals which are bonded to the skeleton via -S (= O) -, such as (C 1 -C 10) -, C 6 ) - or (Ci-C 4 ) -Al kylsulfinyl, z. (But not limited to) (C 1 -C 6) alkylsulfinyl such as methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1, 1-dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl, 2 Methylbutylsulfinyl, 3-methylbutylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethyl-propylsulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1, 1-dimethylbutylsulfinyl, 1, 2-dimethylbutylsulfinyl, 1, 3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1, 1, 2-trimethyl-propylsulfinyl, 1, 2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl and 1-ethyl-2-methylpropylsulfinyl. Analogously, alkenylsulfinyl and alkynylsulfinyl, defined according to the invention as alkenyl or alkynyl radicals which are bonded to the skeleton via -S (= O) -, such as (C 2 -C 10) -, (C 2 -C 6 ) - or (C 2 -) C) -Alkenylsulfinyl or (C3-C10) -, (C 3 -C 6 ) - or (C 3 -C 4 ) -alkynylsulfinyl.
Analog sind Alkenylsulfonyl und Alkinylsulfonyl erfindungsgemäß definiert als Alkenyl- bzw. Alkinylreste, die über -S(=O)2- an das Gerüst gebunden sind, wie (C2-C10)-, (C2- C6)- oder (C2-C )-Alkenylsulfonyl bzw. (C3-C10)-, (C3-C6)- oder (C3-C )-Alkinylsulfonyl. Analogously, alkenylsulfonyl and alkynylsulfonyl are defined according to the invention as alkenyl or alkynyl radicals which are linked to the skeleton via -S (OO) 2, such as (C 2 -C 10) -, (C 2 -C 6 ) - or (C 2 -) C) -alkenylsulfonyl or (C 3 -C 10) -, (C 3 -C 6 ) - or (C 3 -C) -alkynylsulfonyl.
„Alkoxy" bedeutet ein über ein Sauerstoffatom gebundenen Alkylrest, z. B. (aber nicht beschränkt auf) (Ci-Ce)-Alkoxy wie Methoxy, Ethoxy, Propoxy, 1 -Methylethoxy, Butoxy, 1 -Methylpropoxy, 2-Methylpropoxy, 1 ,1 -Dimethylethoxy, Pentoxy, 1 -Methyl- butoxy, 2-Methylbutoxy, 3-Methylbutoxy, 1 ,1 -Dimethylpropoxy, 1 ,2-Dimethylpropoxy, 2,2-Dimethylpropoxy, 1 -Ethylpropoxy, Hexoxy, 1 -Methylpentoxy, 2-Methylpentoxy, 3- Methylpentoxy, 4-Methylpentoxy, 1 ,1 -Dimethylbutoxy, 1 ,2-Dimethylbutoxy, 1 ,3-Di- methylbutoxy, 2,2-Dimethylbutoxy, 2,3-Dimethylbutoxy, 3,3-Dimethylbutoxy, 1 -Ethyl- butoxy, 2-Ethylbutoxy, 1 ,1 ,2-Trimethylpropoxy, 1 ,2,2-Trimethylpropoxy, 1 -Ethyl-1 - methylpropoxy und l -Ethyl-2-methylpropoxy. Alkenyloxy bedeutet ein über ein "Alkoxy" means an alkyl radical bonded through an oxygen atom, for example (but not limited to) (C 1 -C 6) -alkoxy, such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1 , 1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1, 1-dimethylpropoxy, 1, 2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2 Methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1, 1-dimethylbutoxy, 1, 2-dimethylbutoxy, 1, 3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1 ethyl butoxy, 2-ethylbutoxy, 1, 1, 2-trimethylpropoxy, 1, 2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy. Alkenyloxy means one over one
Sauerstoffatom gebundenen Alkenylrest, Alkinyloxy bedeutet ein über ein Oxygen atom bound alkenyl radical, alkynyloxy means one over one
Sauerstoffatom gebundenen Alkinylrest wie (C2-C10)-, (C2-C6)- oder (C2-C4)-Alkenoxy bzw. (C3-C10)-, (Cs-Ce)- oder (C3-C )-Alkinoxy. Alkoxy-bonded alkynyl such as (C 2 -C 10) -, (C 2 -C 6) - or (C 2 -C 4 ) -alkenoxy or (C 3 -C 10) -, (Cs-Ce) - or (C 3 -C) -alkynoxy ,
„Cycloalkyloxy" bedeutet ein über ein Sauerstoffatom gebundenen Cycloalkylrest und Cycloalkenyloxy bedeutet ein über ein Sauerstoffatom gebundenen Cycloalkenylrest. „Alkylcarbonyl" (Alkyl-C(=O)-), soweit nicht an anderer Stelle anders definiert, steht erfindungsgemäß für Alkylreste, die über -C(=O)- an das Gerüst gebunden sind, wie (C1-C10)-, (C1-C6)- oder (Ci-C4)-Alkylcarbonyl. Die Anzahl der C-Atome bezieht sich dabei auf den Alkylrest in der Alkylcarbonylgruppe. Analog stehen„Alkenylcarbonyl" und„Alkinylcarbonyl", soweit nicht an anderer Stelle anders definiert, erfindungsgemäß für Alkenyl- bzw. Alkinylreste, die über -C(=O)- an das Gerüst gebunden sind, wie (C2-C10)-, (C2-C6)- oder (C2-C4)-Alkenylcarbonyl bzw. (C2-C10)-, (C2-C6)- oder (C2-C4)-Alkinylcarbonyl. Die Anzahl der C-Atome bezieht sich dabei auf den Alkenyl- bzw. Alkinylrest in der Alkenyl- bzw. Alkinylcarbonylgruppe. Alkoxycarbonyl (Alkyl-O-C(=O)-), soweit nicht an anderer Stelle anders definiert: "Cycloalkyloxy" denotes a cycloalkyl radical bonded via an oxygen atom and cycloalkenyloxy denotes a cycloalkenyl radical bonded via an oxygen atom. "Alkylcarbonyl" (alkylC (OO) -), unless otherwise defined elsewhere, in accordance with the invention represents alkyl radicals which C (= O) - are attached to the skeleton, such as (C 1 -C 10) -, (C 1 -C 6) - or (C 1 -C 4 ) -alkylcarbonyl. The number of C atoms refers to the alkyl radical in the alkylcarbonyl group. Analogously, "alkenylcarbonyl" and "alkynylcarbonyl" are, unless otherwise defined elsewhere, according to the invention for alkenyl or alkynyl radicals which are bonded to the skeleton via -C (OO) -, such as (C 2 -C 10) -, ( C 2 -C 6) - or (C 2 -C 4 ) -alkenylcarbonyl or (C 2 -C 10) -, (C 2 -C 6) - or (C 2 -C 4 ) -alkynylcarbonyl. The number of C atoms refers to the alkenyl or alkynyl radical in the alkenyl or alkynylcarbonyl group. Alkoxycarbonyl (alkyl-OC (= O) -), unless otherwise defined elsewhere:
Alkylreste, die über -O-C(=O)- an das Gerüst gebunden sind, wie (C1-C10)-, (C1-C6)- oder (Ci-C4)-Alkoxycarbonyl. Die Anzahl der C-Atome bezieht sich dabei auf den Alkylrest in der Alkoxycarbonylgruppe. Alkyl radicals which are bonded to the skeleton via -OC (OO) -, such as (C 1 -C 10) -, (C 1 -C 6) - or (C 1 -C 4 ) -alkoxycarbonyl. The number of C atoms refers to the alkyl radical in the alkoxycarbonyl group.
Analog stehen„Alkenyloxycarbonyl" und„Alkinyloxycarbonyl", soweit nicht an anderer Stelle anders definiert, erfindungsgemäß für Alkenyl- bzw. Alkinylreste, die über -O- C(=O)- an das Gerüst gebunden sind, wie (C2-C10)-, (C2-C6)- oder (C2-C4)-Alkenyloxy- carbonyl bzw. (C3-C10)-, (C3-C6)- oder (C3-C4)-Alkinyloxycarbonyl. Die Anzahl der C- Atome bezieht sich dabei auf den Alkenyl- bzw. Alkinylrest in der Alken- bzw. Analogously, "alkenyloxycarbonyl" and "alkynyloxycarbonyl" are, unless otherwise defined elsewhere, according to the invention for alkenyl or alkynyl radicals which are bonded to the skeleton via -O-C (OO) -, such as (C 2 -C 10) - , (C 2 -C 6) - or (C 2 -C 4 ) -alkenyloxycarbonyl or (C 3 -C 10) -, (C 3 -C 6) - or (C 3 -C 4 ) -alkynyloxycarbonyl. The number of C atoms refers to the alkenyl or alkynyl radical in the alkene or
Alkinyloxycarbonylgruppe. Alkynyloxycarbonyl.
Der Begriff„Alkylcarbonyloxy" (Alkyl-C(=O)-O-) steht erfindungsgemäß, soweit nicht an anderer Stelle anders definiert, für Alkylreste, die über eine Carbonyloxygruppe (- C(=O)-O-) mit dem Sauerstoff an das Gerüst gebunden sind, wie (C1-C10)-, (C1-C6)- oder (Ci-C4)-Alkylcarbonyloxy. Die Anzahl der C-Atome bezieht sich dabei auf den Alkylrest in der Alkylcarbonyloxygruppe. The term "alkylcarbonyloxy" (alkyl-C (= O) -O-) is according to the invention, unless otherwise defined elsewhere, for alkyl radicals which have a carbonyloxy group (- C (= O) -O-) with the oxygen the framework are bound, such as (C1-C10) -, (C1-C6) - or (C 1 -C 4 ) -alkylcarbonyloxy. The number of carbon atoms refers to the alkyl radical in the alkylcarbonyloxy group.
Analog sind„Alkenylcarbonyloxy" und„Alkinylcarbonyloxy" erfindungsgemäß definiert als Alkenyl- bzw. Alkinylreste, die über (-C(=O)-O-) mit dem Sauerstoff an das Gerüst gebunden sind, wie (C2-C10)-, (C2-C6)- oder (C2-C4)-Alkenylcarbonyloxy bzw. (C2-C10)-, (C2-C6)- oder (C2-C4)-Alkinylcarbonyloxy. Die Anzahl der C-Atome bezieht sich dabei auf den Alkenyl- bzw. Alkinylrest in der Alkenyl- bzw. Alkinylcarbonyloxygruppe. Der Begriff„Aryl" bedeutet ein gegebenenfalls substituiertes mono-, bi- oder Analogously, "alkenylcarbonyloxy" and "alkynylcarbonyloxy" are defined according to the invention as alkenyl or alkynyl radicals which are bonded to the skeleton via (-C (OO) -O-), such as (C 2 -C 10) -, (C 2 -C 4) -C 6) - or (C 2 -C 4 ) -alkenylcarbonyloxy or (C 2 -C 10) -, (C 2 -C 6) - or (C 2 -C 4 ) -alkynylcarbonyloxy. The number of C atoms refers to the alkenyl or alkynyl radical in the alkenyl or alkynylcarbonyloxy group. The term "aryl" means an optionally substituted mono-, bi- or
polycyclisches aromatisches System mit vorzugsweise 6 bis 14, insbesondere 6 bis 10 Ring-C-Atomen, beispielsweise Phenyl, Naphthyl, Anthryl, Phenanthrenyl, und ähnliches, vorzugsweise Phenyl. Vom Begriff„gegebenenfalls substituiertes Aryl" sind auch mehrcyclische Systeme, wie Tetrahydronaphtyl, Indenyl, Indanyl, Fluorenyl, Biphenylyl, umfasst, wobei die Bindungsstelle am aromatischen System ist. Von der Systematik her ist„Aryl" in der Regel auch von dem Begriff„gegebenenfalls substituiertes Phenyl" umfasst. polycyclic aromatic system having preferably 6 to 14, in particular 6 to 10 ring C atoms, for example phenyl, naphthyl, anthryl, phenanthrenyl, and the like, preferably phenyl. The term "optionally substituted aryl" also includes polycyclic systems, such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenylyl, the binding site being on the aromatic system. "Aryl" is also generally known from the term "optionally substituted phenyl ".
Bevorzugte Aryl-Substituenten sind hier zum Beispiel Wasserstoff, Halogen, Alkyl, Cycloalkyl, Cycloalkylalkyl, Cycloalkenyl, Halocycloalkyl, Alkenyl, Alkinyl, Aryl, Preferred aryl substituents here are, for example, hydrogen, halogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, halocycloalkyl, alkenyl, alkynyl, aryl,
Arylalkyl, Arylalkenyl, Heteroaryl, Heteroarylalkyl, Heterocyclyl, Heterocyclylalkyl, Alkoxyalkyl, Alkylthio, Haloalkylthio, Haloalkyl, Alkoxy, Haloalkoxy, Cycloalkoxy, Cycloalkylalkoxy, Aryloxy, Heteroraryloxy, Alkoxyalkoxy, Alkinylalkoxy, Alkenyloxy, Bis- alkylaminoalkoxy, Tris-[alkyl]silyl, Bis-[alkyl]arylsilyl, Bis-[alkyl]alkylsilyl, Tris- [alkyl]silylalkinyl, Arylalkinyl, Heteroarylalkinyl, Alkylalkinyl, Cycloalkylalkinyl, Arylalkyl, arylalkenyl, heteroaryl, heteroarylalkyl, heterocyclyl, heterocyclylalkyl, alkoxyalkyl, alkylthio, haloalkylthio, haloalkyl, alkoxy, haloalkoxy, cycloalkoxy, cycloalkylalkoxy, aryloxy, heteroaryloxy, alkoxyalkoxy, alkynylalkoxy, alkenyloxy, bisalkylaminoalkoxy, tris [alkyl] silyl, bis [alkyl] arylsilyl, bis [alkyl] alkylsilyl, tris [alkyl] silylalkynyl, arylalkynyl, heteroarylalkynyl, alkylalkynyl, cycloalkylalkynyl,
Haloalkylalkinyl, Heterocyclyl-N-alkoxy, Nitro, Cyano, Amino, Alkylamino, Bis- alkylamino, Alkylcarbonylamino, Cycloalkylcarbonylamino, Arylcarbonylamino, Haloalkylalkynyl, heterocyclyl-N-alkoxy, nitro, cyano, amino, alkylamino, bisalkylamino, alkylcarbonylamino, cycloalkylcarbonylamino, arylcarbonylamino,
Alkoxycarbonylamino, Alkoxycarbonylalkylamino, Arylalkoxycarbonylalkylamino, Hydroxycarbonyl, Alkoxycarbonyl, Aminocarbonyl, Alkylaminocarbonyl, Alkoxycarbonylamino, alkoxycarbonylalkylamino, arylalkoxycarbonylalkylamino, hydroxycarbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl,
Cycloalkylaminocarbonyl, Bis-Alkylaminocarbonyl, Heteroarylalkoxy, Arylalkoxy Cycloalkylaminocarbonyl, bis-alkylaminocarbonyl, heteroarylalkoxy, arylalkoxy
Ein heterocyclischer Rest (Heterocyclyl) enthält mindestens einen heterocyclischen Ring (=carbocyclischer Ring, in dem mindestens ein C-Atom durch ein Heteroatom ersetzt ist, vorzugsweise durch ein Heteroatom aus der Gruppe N, O, S, P) der gesättigt, ungesättigt, teilgesättigt oder heteroaromatisch ist und dabei unsubstituiert oder substituiert sein kann, wobei die Bindungsstelle an einem Ringatom lokalisiert ist. Ist der Heterocyclylrest oder der heterocyclische Ring gegebenenfalls substituiert, kann er mit anderen carbocyclischen oder heterocyclischen Ringen annelliert sein. Im Falle von gegebenenfalls substituiertem Heterocyclyl werden auch mehrcyclische Systeme umfasst, wie beispielsweise 8-Aza-bicyclo[3.2.1 ]octanyl, 8-Aza- bicyclo[2.2.2]octanyl oder 1 -Aza-bicyclo[2.2.1 ]heptyl. Im Falle von gegebenenfalls substituiertem Heterocyclyl werden auch spirocyclische Systeme umfasst, wie beispielsweise 1 -Oxa-5-aza-spiro[2.3]hexyl. Wenn nicht anders definiert, enthält der heterocyclische Ring vorzugsweise 3 bis 9 Ringatome, insbesondere 3 bis 6 A heterocyclic radical (heterocyclyl) contains at least one heterocyclic ring (= carbocyclic ring in which at least one carbon atom is replaced by a heteroatom, preferably by a heteroatom from the group N, O, S, P) of is saturated, unsaturated, partially saturated or heteroaromatic and may be unsubstituted or substituted, wherein the binding site is located on a ring atom. When the heterocyclyl or heterocyclic ring is optionally substituted, it may be fused with other carbocyclic or heterocyclic rings. In the case of optionally substituted heterocyclyl, polycyclic systems are also included, for example 8-azabicyclo [3.2.1] octanyl, 8-azabicyclo [2.2.2] octanyl or 1-azabicyclo [2.2.1] heptyl. In the case of optionally substituted heterocyclyl, spirocyclic systems are also included, such as 1-oxa-5-aza-spiro [2.3] hexyl. Unless defined otherwise, the heterocyclic ring preferably contains 3 to 9 ring atoms, especially 3 to 6
Ringatome, und ein oder mehrere, vorzugsweise 1 bis 4, insbesondere 1 , 2 oder 3 Heteroatome im heterocyclischen Ring, vorzugsweise aus der Gruppe N, O, und S, wobei jedoch nicht zwei Sauerstoffatome direkt benachbart sein sollen, wie  Ring atoms, and one or more, preferably 1 to 4, in particular 1, 2 or 3 heteroatoms in the heterocyclic ring, preferably from the group N, O, and S, but not two oxygen atoms should be directly adjacent, as
beispielsweise mit einem Heteroatom aus der Gruppe N, O und S 1 - oder 2- oder 3- Pyrrolidinyl, 3,4-Dihydro-2H-pyrrol-2- oder 3-yl, 2,3-Dihydro-1 H-pyrrol-1 - oder 2- oderfor example with a heteroatom from the group N, O and S 1 - or 2- or 3-pyrrolidinyl, 3,4-dihydro-2H-pyrrol-2 or 3-yl, 2,3-dihydro-1 H-pyrrole 1 - or 2 - or
3- oder 4- oder 5-yl; 2,5-Dihydro-1 H-pyrrol-1 - oder 2- oder 3-yl, 1 - oder 2- oder 3- oder3- or 4- or 5-yl; 2,5-dihydro-1H-pyrrol-1 - or 2- or 3-yl, 1- or 2- or 3- or
4- Piperidinyl; 2,3,4,5-Tetrahydropyridin-2- oder 3- oder 4- oder 5-yl oder 6-yl; 1 ,2,3,6- Tetrahydropyridin-1 - oder 2- oder 3- oder 4- oder 5- oder 6-yl; 1 ,2,3,4- Tetrahydropyridin-1 - oder 2- oder 3- oder 4- oder 5- oder 6-yl; 1 ,4-Dihydropyridin-1 - oder 2- oder 3- oder 4-yl; 2,3-Dihydropyridin-2- oder 3- oder 4- oder 5- oder 6-yl; 2,5- Dihydropyridin-2- oder 3- oder 4- oder 5- oder 6-yl, 1 - oder 2- oder 3- oder 4-Azepanyl; 2,3,4,5-Tetrahydro-1 H-azepin-1 - oder 2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 4-piperidinyl; 2,3,4,5-tetrahydropyridine-2- or 3- or 4- or 5-yl or 6-yl; 1, 2,3,6-tetrahydropyridine-1 - or 2- or 3- or 4- or 5- or 6-yl; 1, 2,3,4-tetrahydropyridine-1 - or 2- or 3- or 4- or 5- or 6-yl; 1,4-dihydropyridine-1 - or 2- or 3- or 4-yl; 2,3-dihydropyridine-2- or 3- or 4- or 5- or 6-yl; 2,5-dihydropyridine-2- or 3- or 4- or 5- or 6-yl, 1- or 2- or 3- or 4-azepanyl; 2,3,4,5-tetrahydro-1H-azepine-1 - or 2- or 3- or 4- or 5- or 6- or 7-yl;
2,3,4,7-Tetrahydro-1 H-azepin-1 - oder 2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,4,7-tetrahydro-1H-azepine-1 - or 2- or 3- or 4- or 5- or 6- or 7-yl;
2,3,6,7-Tetrahydro-1 H-azepin-1 - oder 2- oder 3- oder 4-yl; 3,4,5,6-Tetrahydro-2H- azepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 4,5-Dihydro-1 H-azepin-1 - oder 2- oder 3- oder 4-yl; 2,5-Dihydro-1 H-azepin-1 - oder -2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,7-Dihydro-1 H-azepin-1 - oder -2- oder 3- oder 4-yl; 2,3-Dihydro-1 H-azepin- 1 - oder -2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 3,4-Dihydro-2H-azepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 3,6-Dihydro-2H-azepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 5,6-Dihydro-2H-azepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 4,5-Dihydro-3H-azepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 1 H-Azepin-1 - oder -2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2H-Azepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 3H-Azepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 4H-Azepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl, 2- oder 3-Oxolanyl (= 2- oder 3-Tetrahydrofuranyl); 2,3-Dihydrofuran-2- oder 3- oder 4- oder 5-yl; 2,5-Dihydrofuran-2- oder 3-yl, 2- oder 3- oder 4-Oxanyl (= 2- oder 3- oder 4-Tetrahydropyranyl); 3,4-Dihydro-2H-pyran-2- oder2,3,6,7-tetrahydro-1H-azepine-1 - or 2- or 3- or 4-yl; 3,4,5,6-tetrahydro-2H-azepine-2 or 3 or 4 or 5 or 6 or 7-yl; 4,5-dihydro-1H-azepine-1 - or 2- or 3- or 4-yl; 2,5-dihydro-1H-azepine-1 or -2 or 3 or 4 or 5 or 6 or 7-yl; 2,7-dihydro-1H-azepine-1 - or -2- or 3- or 4-yl; 2,3-dihydro-1H-azepine-1 - or -2- or 3- or 4- or 5- or 6- or 7-yl; 3,4-dihydro-2H-azepine-2 or 3 or 4 or 5 or 6 or 7-yl; 3,6-dihydro-2H-azepine-2 or 3 or 4 or 5 or 6 or 7-yl; 5,6-dihydro-2H-azepine-2 or 3 or 4 or 5 or 6 or 7-yl; 4,5-dihydro-3H-azepine-2 or 3 or 4 or 5 or 6 or 7-yl; 1 H-azepine-1 or -2 or 3 or 4 or 5 or 6 or 7-yl; 2H-azepine-2- or 3- or 4- or 5- or 6- or 7-yl; 3H-azepine-2- or 3- or 4- or 5- or 6- or 7-yl; 4H-azepine-2- or 3- or 4- or 5- or 6- or 7-yl, 2- or 3-oxolanyl (= 2- or 3-tetrahydrofuranyl); 2,3-dihydrofuran-2- or 3- or 4- or 5-yl; 2,5-dihydrofuran-2- or 3-yl, 2- or 3- or 4-oxanyl (= 2- or 3- or 4-tetrahydropyranyl); 3,4-dihydro-2H-pyran-2-or
3- oder 4- oder 5- oder 6-yl; 3,6-Dihydro-2H-pyran-2- oder 3-oder 4- oder 5- oder 6-yl; 2H-Pyran-2- oder 3- oder 4- oder 5- oder 6-yl; 4H-Pyran-2- oder 3- oder 4-yl, 2- oder 3- oder 4-Oxepanyl; 2,3,4,5-Tetrahydrooxepin-2- oder 3- oder 4- oder 5- oder 6- oder 7- yl; 2,3,4,7-Tetrahydrooxepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,6,7- Tetrahydrooxepin-2- oder 3- oder 4-yl; 2,3-Dihydrooxepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 4,5-Dihydrooxepin-2- oder 3- oder 4-yl; 2,5-Dihydrooxepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; Oxepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2- oder 3-Tetrahydrothiophenyl; 2,3-Dihydrothiophen-2- oder 3- oder 4- oder 5-yl; 2,5- Dihydrothiophen-2- oder 3-yl; Tetrahydro-2H-thiopyran-2- oder 3- oder 4-yl; 3,4- Dihydro-2H-thiopyran-2- oder 3- oder 4- oder 5- oder 6-yl; 3,6-Dihydro-2H-thiopyran-3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-pyran-2 or 3 or 4 or 5 or 6-yl; 2H-pyran-2- or 3- or 4- or 5- or 6-yl; 4H-pyran-2- or 3- or 4-yl, 2- or 3- or 4-oxepanyl; 2,3,4,5-tetrahydrooxepin-2 or 3 or 4 or 5 or 6 or 7 yl; 2,3,4,7-tetrahydrooxepin-2 or 3 or 4 or 5 or 6 or 7-yl; 2,3,6,7-tetrahydrooxepin-2 or 3 or 4-yl; 2,3-dihydrooxepin-2 or 3 or 4 or 5 or 6 or 7-yl; 4,5-dihydrooxepin-2 or 3 or 4-yl; 2,5-dihydrooxepin-2 or 3 or 4 or 5 or 6 or 7-yl; Oxepin-2 or 3 or 4 or 5 or 6 or 7-yl; 2- or 3-tetrahydrothiophenyl; 2,3-dihydrothiophene-2 or 3 or 4 or 5-yl; 2,5-dihydrothiophene-2 or 3-yl; Tetrahydro-2H-thiopyran-2- or 3- or 4-yl; 3,4-dihydro-2H-thiopyran-2 or 3 or 4 or 5 or 6-yl; 3,6-dihydro-2H-thiopyran
2- oder 3- oder 4- oder 5- oder 6-yl; 2H-Thiopyran-2- oder 3- oder 4- oder 5- oder 6-yl; 4H-Thiopyran-2- oder 3- oder 4-yl. Bevorzugte 3-Ring und 4-Ring-Heterocyclen sind beispielsweise 1 - oder 2-Aziridinyl, Oxiranyl, Thiiranyl, 1 - oder 2- oder 3-Azetidinyl, 2- oder 3-Oxetanyl, 2- oder 3-Thietanyl, 1 ,3-Dioxetan-2-yl. Weitere Beispiele für 2- or 3- or 4- or 5- or 6-yl; 2H-thiopyran-2 or 3 or 4 or 5 or 6-yl; 4H-thiopyran-2- or 3- or 4-yl. Preferred 3-membered and 4-membered heterocycles are, for example, 1- or 2-aziridinyl, oxiranyl, thiiranyl, 1- or 2- or 3-azetidinyl, 2- or 3-oxetanyl, 2- or 3-thietanyl, 1,3 -Dioxetan-2-yl. Further examples of
"Heterocyclyl" sind ein partiell oder vollständig hydrierter heterocyclischer Rest mit zwei Heteroatomen aus der Gruppe N, O und S, wie beispielsweise 1 - oder 2- oder 3- oder 4-Pyrazolidinyl; 4,5-Dihydro-3H-pyrazol- 3- oder 4- oder 5-yl; 4,5-Dihydro-1 H- pyrazol-1 - oder 3- oder 4- oder 5-yl; 2,3-Dihydro-1 H-pyrazol-1 - oder 2- oder 3- oder 4- oder 5-yl; 1 - oder 2- oder 3- oder 4- Imidazolidinyl; 2,3-Dihydro-1 H-imidazol-1 - oder 2- oder 3- oder 4-yl; 2,5-Dihydro-1 H-imidazol-1 - oder 2- oder 4- oder 5-yl; 4,5-Dihydro- 1 H-imidazol-1 - oder 2- oder 4- oder 5-yl; Hexahydropyridazin-1 - oder 2- oder 3- oder"Heterocyclyl" are a partially or fully hydrogenated heterocyclic radical having two heteroatoms from the group N, O and S, such as 1- or 2- or 3- or 4-pyrazolidinyl; 4,5-dihydro-3H-pyrazole-3 or 4 or 5-yl; 4,5-dihydro-1H-pyrazole-1 - or 3- or 4- or 5-yl; 2,3-dihydro-1H-pyrazole-1 - or 2- or 3- or 4- or 5-yl; 1- or 2- or 3- or 4-imidazolidinyl; 2,3-dihydro-1H-imidazole-1 - or 2- or 3- or 4-yl; 2,5-dihydro-1H-imidazole-1 - or 2- or 4- or 5-yl; 4,5-dihydro-1H-imidazole-1 - or 2- or 4- or 5-yl; Hexahydropyridazine-1 - or 2- or 3- or
4- yl; 1 ,2,3,4-Tetrahydropyridazin-1 - oder 2- oder 3- oder 4- oder 5- oder 6-yl; 1 ,2,3,6- Tetrahydropyridazin-1 - oder 2- oder 3- oder 4- oder 5- oder 6-yl; 1 ,4,5,6-4-yl; 1,2,3,4-tetrahydropyridazine-1 - or 2- or 3- or 4- or 5- or 6-yl; 1, 2,3,6-tetrahydropyridazine-1 - or 2- or 3- or 4- or 5- or 6-yl; 1, 4,5,6-
Tetrahydropyridazin-1 - oder 3- oder 4- oder 5- oder 6-yl; 3,4,5,6-Tetrahydropyridazin-Tetrahydropyridazine-1 - or 3- or 4- or 5- or 6-yl; 3,4,5,6-Tetrahydropyridazin-
3- oder 4- oder 5-yl; 4,5-Dihydropyridazin-3- oder 4-yl; 3,4-Dihydropyridazin-3- oder 4- oder 5- oder 6-yl; 3,6-Dihydropyridazin-3- oder 4-yl; 1 ,6-Dihydropyriazin-1 - oder 3- oder 4- oder 5- oder 6-yl; Hexahydropyrimidin-1 - oder 2- oder 3- oder 4-yl; 1 ,4,5,6- Tetrahydropyrimidin-1 - oder 2- oder 4- oder 5- oder 6-yl; 1 ,2,5,6-Tetrahydropyrimidin- 1 - oder 2- oder 4- oder 5- oder 6-yl; 1 ,2,3,4-Tetrahydropyrimidin-1 - oder 2- oder 3- oder 4- oder 5- oder 6-yl; 1 ,6-Dihydropyrimidin-1 - oder 2- oder 4- oder 5- oder 6-yl; 1 ,2-Dihydropyrimidin-1 - oder 2- oder 4- oder 5- oder 6-yl; 2,5-Dihydropyrimidin-2- oder3- or 4- or 5-yl; 4,5-dihydropyridazine-3 or 4-yl; 3,4-dihydropyridazine-3- or 4- or 5- or 6-yl; 3,6-dihydropyridazine-3 or 4-yl; 1,6-dihydropyriazine-1 - or 3- or 4- or 5- or 6-yl; Hexahydropyrimidine-1 - or 2- or 3- or 4-yl; 1, 4,5,6-tetrahydropyrimidine-1 - or 2- or 4- or 5- or 6-yl; 1, 2,5,6-tetrahydropyrimidine-1 - or 2- or 4- or 5- or 6-yl; 1,2,3,4-tetrahydropyrimidine-1 - or 2- or 3- or 4- or 5- or 6-yl; 1,6-dihydropyrimidine-1 - or 2- or 4- or 5- or 6-yl; 1,2-dihydropyrimidine-1 - or 2- or 4- or 5- or 6-yl; 2,5-dihydropyrimidine-2- or
4- oder 5-yl; 4,5-Dihydropyrimidin- 4- oder 5- oder 6-yl; 1 ,4-Dihydropyrimidin-1 - oder 2- oder 4- oder 5- oder 6-yl; 1 - oder 2- oder 3-Piperazinyl; 1 ,2,3,6-Tetrahydropyrazin-1 - oder 2- oder 3- oder 5- oder 6-yl; 1 ,2,3,4-Tetrahydropyrazin-1 - oder 2- oder 3- oder 4- oder 5- oder 6-yl; 1 ,2-Dihydropyrazin-1 - oder 2- oder 3- oder 5- oder 6-yl; 1 ,4- Dihydropyrazin-1 - oder 2- oder 3-yl; 2,3-Dihydropyrazin-2- oder 3- oder 5- oder 6-yl; 2,5-Dihydropyrazin-2- oder 3-yl; 1 ,3-Dioxolan-2- oder 4- oder 5-yl; 1 ,3-Dioxol-2- oder 4-yl; 1 ,3-Dioxan-2- oder 4- oder 5-yl; 4H-1 ,3-Dioxin-2- oder 4- oder 5- oder 6-yl; 1 ,4- Dioxan-2- oder 3- oder 5- oder 6-yl; 2,3-Dihydro-1 ,4-dioxin-2- oder 3- oder 5- oder 6-yl; 1 ,4-Dioxin-2- oder 3-yl; 1 ,2-Dithiolan-3- oder 4-yl; 3H-1 ,2-Dithiol-3- oder 4- oder 5-yl;4- or 5-yl; 4,5-dihydropyrimidine-4- or 5- or 6-yl; 1,4-dihydropyrimidine-1 - or 2- or 4- or 5- or 6-yl; 1- or 2- or 3-piperazinyl; 1,2,3,6-tetrahydropyrazine-1 - or 2- or 3- or 5- or 6-yl; 1,2,3,4-tetrahydropyrazine-1 - or 2- or 3- or 4- or 5- or 6-yl; 1,2-dihydropyrazine-1 - or 2- or 3- or 5- or 6-yl; 1,4-dihydropyrazine-1 - or 2- or 3-yl; 2,3-dihydropyrazine-2- or 3- or 5- or 6-yl; 2,5-dihydropyrazine-2 or 3-yl; 1,3-dioxolane-2- or 4- or 5-yl; 1,3-dioxol-2- or 4-yl; 1,3-dioxane-2- or 4- or 5-yl; 4H-1, 3-dioxin-2 or 4 or 5 or 6-yl; 1, 4-dioxane-2 or 3 or 5 or 6-yl; 2,3-dihydro-1,4-dioxin-2- or 3- or 5- or 6-yl; 1, 4-dioxin-2 or 3-yl; 1,2-dithiolan-3 or 4-yl; 3H-1,2-dithiol-3- or 4- or 5-yl;
1 .3- Dithiolan-2- oder 4-yl; 1 ,3-Dithiol-2- oder 4-yl; 1 ,2-Dithian-3- oder 4-yl; 3,4-Dihydro- 1 ,2-dithiin-3- oder 4- oder 5- oder 6-yl; 3,6-Dihydro-1 ,2-dithiin-3- oder 4-yl; 1 ,2-Dithiin-1, 3-dithiolan-2 or 4-yl; 1,3-dithiol-2- or 4-yl; 1,2-dithian-3 or 4-yl; 3,4-dihydro-1,2-dithiin-3- or 4- or 5- or 6-yl; 3,6-dihydro-1,2-dithiin-3 or 4-yl; 1, 2-dithinine
3- oder 4-yl; 1 ,3-Dithian-2- oder 4- oder 5-yl; 4H-1 ,3-Dithiin-2- oder 4- oder 5- oder 6- yl; lsoxazolidin-2- oder 3- oder 4- oder 5-yl; 2,3-Dihydroisoxazol-2- oder 3- oder 4- oder 5-yl; 2,5-Dihydroisoxazol-2- oder 3- oder 4- oder 5-yl; 4,5-Dihydroisoxazol-3- oder3- or 4-yl; 1,3-dithian-2- or 4- or 5-yl; 4H-1, 3-dithiine-2 or 4 or 5 or 6 yl; Isoxazolidine-2 or 3 or 4 or 5-yl; 2,3-dihydroisoxazole-2 or 3 or 4 or 5-yl; 2,5-dihydroisoxazole-2 or 3 or 4 or 5-yl; 4,5-dihydroisoxazole-3- or
4- oder 5-yl; 1 ,3-Oxazolidin-2- oder 3- oder 4- oder 5-yl; 2,3-Dihydro-1 ,3-oxazol-2- oder 3- oder 4- oder 5-yl; 2,5-Dihydro-1 ,3-oxazol-2- oder 4- oder 5-yl; 4,5-Dihydro-1 ,3- oxazol-2- oder 4- oder 5-yl; 1 ,2-Oxazinan-2- oder 3- oder 4- oder 5- oder 6-yl; 3,4- Dihydro-2H-1 ,2-oxazin-2- oder 3- oder 4- oder 5- oder 6-yl; 3,6-Dihydro-2H-1 ,2-oxazin- 2- oder 3- oder 4- oder 5- oder 6-yl; 5,6-Dihydro-2H-1 ,2-oxazin-2- oder 3- oder 4- oder4- or 5-yl; 1,3-oxazolidine-2- or 3- or 4- or 5-yl; 2,3-dihydro-1,3-oxazol-2- or 3- or 4- or 5-yl; 2,5-dihydro-1,3-oxazol-2- or 4- or 5-yl; 4,5-dihydro-1,3-oxazol-2 or 4 or 5-yl; 1, 2-oxazinan-2 or 3 or 4 or 5 or 6-yl; 3,4-dihydro-2H-1,2-oxazine-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-1,2-oxazine-2- or 3- or 4- or 5- or 6-yl; 5,6-dihydro-2H-1, 2-oxazine-2 or 3 or 4 or
5- oder 6-yl; 5,6-Dihydro-4H-1 ,2-oxazin-3- oder 4- oder 5- oder 6-yl; 2H-1 ,2-Oxazin-2- oder 3- oder 4- oder 5- oder 6-yl; 6H-1 ,2-Oxazin-3- oder 4- oder 5- oder 6-yl; 4H-1 ,2-5- or 6-yl; 5,6-dihydro-4H-1,2-oxazine-3- or 4- or 5- or 6-yl; 2H-1, 2-oxazine-2 or 3 or 4 or 5 or 6-yl; 6H-1, 2-oxazine-3 or 4 or 5 or 6-yl; 4H-1, 2-
Oxazin-3- oder 4- oder 5- oder 6-yl; 1 ,3-Oxazinan-2- oder 3- oder 4- oder 5- oder 6-yl;Oxazine-3- or 4- or 5- or 6-yl; 1,3-oxazinan-2 or 3 or 4 or 5 or 6-yl;
3.4- Dihydro-2H-1 ,3-oxazin-2- oder 3- oder 4- oder 5- oder 6-yl; 3,6-Dihydro-2H-1 ,3- oxazin-2- oder 3- oder 4- oder 5- oder 6-yl; 5,6-Dihydro-2H-1 ,3-oxazin-2- oder 4- oder 5- oder 6-yl; 5,6-Dihydro-4H-1 ,3-oxazin-2- oder 4- oder 5- oder 6-yl; 2H-1 ,3-Oxazin-2- oder 4- oder 5- oder 6-yl; 6H-1 ,3-Oxazin-2- oder 4- oder 5- oder 6-yl; 4H-1 ,3-Oxazin-2- oder 4- oder 5- oder 6-yl; Morpholin-2- oder 3- oder 4-yl; 3,4-Dihydro-2H-1 ,4-oxazin-2- oder 3- oder 4- oder 5- oder 6-yl; 3,6-Dihydro-2H-1 ,4-oxazin-2- oder 3- oder 5- oder 6- yl; 2H-1 ,4-oxazin-2- oder 3- oder 5- oder 6-yl; 4H-1 ,4-oxazin-2- oder 3-yl; 1 ,2- Oxazepan-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,4,5-Tetrahydro-1 ,2- oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,4,7-Tetrahydro-1 ,2-oxazepin- 2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,6,7-Tetrahydro-1 ,2-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,5,6,7-Tetrahydro-1 ,2-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 4,5,6,7-Tetrahydro-1 ,2-oxazepin-3- oder 4- oder 5- oder 6- oder 7-yl; 2,3-Dihydro-1 ,2-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,5- Dihydro-1 ,2-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,7-Dihydro-1 ,2- oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 4,5-Dihydro-1 ,2-oxazepin-3- oder 4- oder 5- oder 6- oder 7-yl; 4,7-Dihydro-1 ,2-oxazepin-3- oder 4- oder 5- oder 6- oder 7-yl; 6,7-Dihydro-1 ,2-oxazepin-3- oder 4- oder 5- oder 6- oder 7-yl; 1 ,2-Oxazepin-3- oder 4- oder 5- oder 6- oder 7-yl; 1 ,3-Oxazepan-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,4,5-Tetrahydro-1 ,3-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 3,4-dihydro-2H-1,3-oxazine-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-1, 3-oxazine-2 or 3 or 4 or 5 or 6-yl; 5,6-dihydro-2H-1,3-oxazine-2- or 4- or 5- or 6-yl; 5,6-dihydro-4H-1,3-oxazine-2- or 4- or 5- or 6-yl; 2H-1, 3-oxazine-2- or 4- or 5- or 6-yl; 6H-1, 3-oxazine-2 or 4 or 5 or 6-yl; 4H-1, 3-oxazine-2 or 4 or 5 or 6-yl; Morpholine-2- or 3- or 4-yl; 3,4-dihydro-2H-1,4-oxazine-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-1,4-oxazine-2 or 3 or 5 or 6-yl; 2H-1,4-oxazine-2- or 3- or 5- or 6-yl; 4H-1,4-oxazine-2 or 3-yl; 1, 2- oxazepan-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,5-tetrahydro-1,2,10-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-tetrahydro-1,2-oxazepine 2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-tetrahydro-1,2-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5,6,7-tetrahydro-1,2-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 4,5,6,7-tetrahydro-1,2-oxazepine-3- or 4- or 5- or 6- or 7-yl; 2,3-dihydro-1,2-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5- Dihydro-1,2-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,7-dihydro-1, 2-oxazepine-2 or 3 or 4 or 5 or 6 or 7-yl; 4,5-dihydro-1,2-oxazepine-3- or 4- or 5- or 6- or 7-yl; 4,7-dihydro-1,2-oxazepine-3- or 4- or 5- or 6- or 7-yl; 6,7-dihydro-1,2-oxazepine-3- or 4- or 5- or 6- or 7-yl; 1,2-oxazepine-3- or 4- or 5- or 6- or 7-yl; 1,3-oxazepan-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,5-tetrahydro-1,3-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl;
2,3,4,7-Tetrahydro-1 ,3-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,6,7- Tetrahydro-1 ,3-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,5,6,7- Tetrahydro-1 ,3-oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; 4,5,6,7-Tetrahydro-1 ,3- oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; 2,3-Dihydro-1 ,3-oxazepin-2- oder 3- oder2,3,4,7-tetrahydro-1,3-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-tetrahydro-1,3-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5,6,7-tetrahydro-1,3-oxazepine-2- or 4- or 5- or 6- or 7-yl; 4,5,6,7-tetrahydro-1,3,10-oxazepine-2- or 4- or 5- or 6- or 7-yl; 2,3-dihydro-1,3-oxazepine-2- or 3- or
4- oder 5- oder 6- oder 7-yl; 2,5-Dihydro-1 ,3-oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; 2,7-Dihydro-1 ,3-oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; 4,5-Dihydro-1 ,3- oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; 4,7-Dihydro-1 ,3-oxazepin-2- oder 4- oder4- or 5- or 6- or 7-yl; 2,5-dihydro-1,3-oxazepine-2- or 4- or 5- or 6- or 7-yl; 2,7-dihydro-1,3-oxazepine-2- or 4- or 5- or 6- or 7-yl; 4,5-dihydro-1,3-oxazepine-2- or 4- or 5- or 6- or 7-yl; 4,7-dihydro-1,3-oxazepine-2- or 4- or
5- oder 6- oder 7-yl; 6,7-Dihydro-1 ,3-oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; 1 ,3-Oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; 1 ,4-Oxazepan-2- oder 3- oder 5- oder 6- oder 7-yl; 2,3,4,5-Tetrahydro-1 ,4-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,4,7-Tetrahydro-1 ,4-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,6,7-Tetrahydro-1 ,4-oxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; 2,5,6,7- Tetrahydro-1 ,4-oxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; 4,5,6,7-Tetrahydro-1 ,4- oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3-Dihydro-1 ,4-oxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; 2,5-Dihydro-1 ,4-oxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; 2,7-Dihydro-1 ,4-oxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; 4,5-Dihydro-1 ,4- oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 4,7-Dihydro-1 ,4-oxazepin-2- oder5- or 6- or 7-yl; 6,7-dihydro-1,3-oxazepine-2- or 4- or 5- or 6- or 7-yl; 1,3-oxazepine-2- or 4- or 5- or 6- or 7-yl; 1,4-oxazepan-2- or 3- or 5- or 6- or 7-yl; 2,3,4,5-tetrahydro-1,4-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-tetrahydro-1,4-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-tetrahydro-1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl; 2,5,6,7-tetrahydro-1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl; 4,5,6,7-tetrahydro-1, 4-oxazepine-2 or 3 or 4 or 5 or 6 or 7-yl; 2,3-dihydro-1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl; 2,5-dihydro-1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl; 2,7-dihydro-1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl; 4,5-dihydro-1,4-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 4,7-Dihydro-1,4-oxazepine-2-Or
3- oder 4- oder 5- oder 6- oder 7-yl; 6,7-Dihydro-1 ,4-oxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; 1 ,4-Oxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; lsothiazolidin-2- oder 3- oder 4- oder 5-yl; 2,3-Dihydroisothiazol-2- oder 3- oder 4- oder 5-yl; 2,5- Dihydroisothiazol-2- oder 3- oder 4- oder 5-yl; 4,5-Dihydroisothiazol-3- oder 4- oder 5- yl; 1 ,3-Thiazolidin-2- oder 3- oder 4- oder 5-yl; 2,3-Dihydro-1 ,3-thiazol-2- oder 3- oder3- or 4- or 5- or 6- or 7-yl; 6,7-dihydro-1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl; 1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl; isothiazolidine-2- or 3- or 4- or 5-yl; 2,3-dihydroisothiazole-2- or 3- or 4- or 5-yl; 2,5-dihydroisothiazole-2 or 3 or 4 or 5-yl; 4,5-dihydroisothiazole-3 or 4 or 5-yl; 1,3-thiazolidine-2- or 3- or 4- or 5-yl; 2,3-dihydro-1, 3-thiazole-2 or 3 or
4- oder 5-yl; 2,5-Dihydro-1 ,3-thiazol-2- oder 4- oder 5-yl; 4,5-Dihydro-1 ,3-thiazol-2- oder 4- oder 5-yl; 1 ,3-Thiazinan-2- oder 3- oder 4- oder 5- oder 6-yl; 3,4-Dihydro-2H-4- or 5-yl; 2,5-dihydro-1,3-thiazole-2 or 4 or 5-yl; 4,5-dihydro-1,3-thiazole-2- or 4- or 5-yl; 1, 3-thiazinan-2 or 3 or 4 or 5 or 6-yl; 3,4-dihydro-2H
1 ,3-thiazin-2- oder 3- oder 4- oder 5- oder 6-yl; 3,6-Dihydro-2H-1 ,3-thiazin-2- oder 3- oder 4- oder 5- oder 6-yl; 5,6-Dihydro-2H-1 ,3-thiazin-2- oder 4- oder 5- oder 6-yl; 5,6- Dihydro-4H-1 ,3-thiazin-2- oder 4- oder 5- oder 6-yl; 2H-1 ,3-Thiazin-2- oder 4- oder 5- oder 6-yl; 6H-1 ,3-Thiazin-2- oder 4- oder 5- oder 6-yl; 4H-1 ,3-Thiazin-2- oder 4- oder 5- oder 6-yl. Weitere Beispiele für "Heterocyclyl" sind ein partiell oder vollständig hydrierter heterocyclischer Rest mit 3 Heteroatomen aus der Gruppe N, O und S, wie beispielsweise 1 ,4,2-Dioxazolidin-2- oder 3- oder 5-yl; 1 ,4,2-Dioxazol-3- oder 5-yl;1, 3-thiazine-2 or 3 or 4 or 5 or 6-yl; 3,6-dihydro-2H-1, 3-thiazine-2 or 3 or 4 or 5 or 6-yl; 5,6-dihydro-2H-1, 3-thiazine-2 or 4 or 5 or 6-yl; 5,6-dihydro-4H-1, 3-thiazine-2 or 4 or 5 or 6-yl; 2H-1, 3-thiazine-2 or 4 or 5 or 6-yl; 6H-1, 3-thiazine-2 or 4 or 5 or 6-yl; 4H-1, 3-thiazine-2 or 4 or 5- or 6-yl. Further examples of "heterocyclyl" are a partially or fully hydrogenated heterocyclic radical having 3 heteroatoms from the group N, O and S, such as, for example, 1, 4,2-dioxazolidin-2 or 3 or 5-yl; 1, 4,2-dioxazol-3 or 5-yl;
1 ,4,2-Dioxazinan-2- oder -3- oder 5- oder 6-yl; 5,6-Dihydro-1 ,4,2-dioxazin-3- oder 5- oder 6-yl; 1 ,4,2-Dioxazin-3- oder 5- oder 6-yl; 1 ,4,2-Dioxazepan-2- oder 3- oder 5- oder1,2,2-dioxazinane-2- or -3- or 5- or 6-yl; 5,6-dihydro-1,2,2,2-dioxazine-3- or 5- or 6-yl; 1,2,2-dioxazine-3- or 5- or 6-yl; 1, 4,2-Dioxazepan-2 or 3 or 5 or
6- oder 7-yl; 6,7-Dihydro-5H-1 ,4,2-Dioxazepin-3- oder 5- oder 6- oder 7-yl; 2,3- Dihydro-7H-1 ,4,2-Dioxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; 2,3-Dihydro-5H-6- or 7-yl; 6,7-dihydro-5H-1, 4,2-dioxazepine-3 or 5 or 6 or 7-yl; 2,3-dihydro-7H-1,2,2-dioxazepine-2- or 3- or 5- or 6- or 7-yl; 2,3-dihydro-5H-
1 ,4,2-Dioxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; 5H-1 ,4,2-Dioxazepin-3- oder 5- oder 6- oder 7-yl; 7H-1 ,4,2-Dioxazepin-3- oder 5- oder 6- oder 7-yl. Strukturbeispiele für gegebenenfalls weiter substituierte Heterocyclen sind auch im Folgenden 1,2,2-dioxazepine-2- or 3- or 5- or 6- or 7-yl; 5H-1, 4,2-dioxazepine-3 or 5 or 6 or 7-yl; 7H-1, 4,2-dioxazepine-3 or 5 or 6 or 7-yl. Structural examples of optionally further substituted heterocycles are also mentioned below
aufgeführt: listed:
Die oben aufgeführten Heterocyclen sind bevorzugt beispielsweise durch Wasserstoff, Halogen, Alkyl, Haloalkyl, Hydroxy, Alkoxy, Cycloalkoxy, Aryloxy, Alkoxyalkyl, The heterocycles listed above are preferably, for example, hydrogen, halogen, alkyl, haloalkyl, hydroxy, alkoxy, cycloalkoxy, aryloxy, alkoxyalkyl,
Alkoxyalkoxy, Cycloalkyl, Halocycloalkyl, Aryl, Arylalkyl, Heteroaryl, Heterocyclyl, Alkenyl, Alkylcarbonyl, Cycloalkylcarbonyl, Arylcarbonyl, Heteroarylcarbonyl, Alkoxyalkoxy, cycloalkyl, halocycloalkyl, aryl, arylalkyl, heteroaryl, heterocyclyl, alkenyl, alkylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl,
Alkoxycarbonyl, Hydroxycarbonyl, Cycloalkoxycarbonyl, Cycloalkylalkoxycarbonyl, Alkoxycarbonylalkyl, Arylalkoxycarbonyl, Arylalkoxycarbonylalkyl, Alkinyl, Alkinylalkyl, Alkylalkinyl, Tris-alkylsilylalkinyl, Nitro, Amino, Cyano, Haloalkoxy, Haloalkylthio, Alkylthio, Hydrothio, Hydroxyalkyl, Oxo, Heteroarylalkoxy, Arylalkoxy,  Alkoxycarbonyl, hydroxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, alkoxycarbonylalkyl, arylalkoxycarbonyl, arylalkoxycarbonylalkyl, alkynyl, alkynylalkyl, alkylalkynyl, trisalkylsilylalkynyl, nitro, amino, cyano, haloalkoxy, haloalkylthio, alkylthio, hydrothio, hydroxyalkyl, oxo, heteroarylalkoxy, arylalkoxy,
Heterocyclylalkoxy, Heterocyclylalkylthio, Heterocyclyloxy, Heterocyclylthio, Heterocyclylalkoxy, heterocyclylalkylthio, heterocyclyloxy, heterocyclylthio,
Heteroaryloxy, Bis-alkylamino, Alkylamino, Cycloalkylamino, Heteroaryloxy, bis-alkylamino, alkylamino, cycloalkylamino,
Hydroxycarbonylalkylannino, Alkoxycarbonylalkylannino, Arylalkoxycarbonylalkylannino, Alkoxycarbonylalkyl(alkyl)amino, Aminocarbonyl, Alkylaminocarbonyl, Bis- alkylaminocarbonyl, Cycloalkylaminocarbonyl, Hydroxycarbonylalkylaminocarbonyl, Alkoxycarbonylalkylaminocarbonyl, Arylalkoxycarbonylalkylaminocarbonyl substituiert.  Hydroxycarbonylalkylannino, alkoxycarbonylalkylannino, arylalkoxycarbonylalkylannino, alkoxycarbonylalkyl (alkyl) amino, aminocarbonyl, alkylaminocarbonyl, bis-alkylaminocarbonyl, cycloalkylaminocarbonyl, hydroxycarbonylalkylaminocarbonyl, alkoxycarbonylalkylaminocarbonyl, arylalkoxycarbonylalkylaminocarbonyl.
Wenn ein Grundkörper "durch einen oder mehrere Reste" aus einer Aufzählung von Resten (= Gruppe) oder einer generisch definierten Gruppe von Resten substituiert ist, so schließt dies jeweils die gleichzeitige Substitution durch mehrere gleiche und/oder strukturell unterschiedliche Reste ein. If a main body is "substituted by one or more radicals" from an enumeration of radicals (= group) or a generically defined group of radicals, this includes the simultaneous substitution by several identical and / or structurally different radicals.
Handelt es sich es sich um einen teilweise oder vollständig gesättigten Stickstoff- Heterocyclus, so kann dieser sowohl über Kohlenstoff als auch über den Stickstoff mit dem Rest des Moleküls verknüpft sein. If it is a partially or fully saturated nitrogen heterocycle, it may be linked to the rest of the molecule via both carbon and nitrogen.
Als Substituenten für einen substituierten heterocyclischen Rest kommen die weiter unten genannten Substituenten in Frage, zusätzlich auch Oxo und Thioxo. Die Suitable substituents for a substituted heterocyclic radical are the substituents mentioned below, in addition to oxo and thioxo. The
Oxogruppe als Substituent an einem Ring-C-Atom bedeutet dann beispielsweise eine Carbonylgruppe im heterocyclischen Ring. Dadurch sind vorzugsweise auch Lactone und Lactame umfasst. Die Oxogruppe kann auch an den Heteroringatomen, die in verschiedenen Oxidationsstufen existieren können, z.B. bei N und S, auftreten und bilden dann beispielsweise die divalenten Gruppen N(O) , S(O) (auch kurz SO) und S(O)2 (auch kurz SO2) im heterocyclischen Ring. Im Fall von -N(O)- und -S(O)- Gruppen sind jeweils beide Enantiomere umfasst. Oxo group as a substituent on a ring C atom then means, for example, a carbonyl group in the heterocyclic ring. As a result, lactones and lactams are preferably also included. The oxo group may also be attached to the hetero ring atoms, which may exist in different oxidation states, e.g. in the case of N and S, for example, the divalent groups N (O), S (O) (also SO for short) and S (O) 2 (also SO2 for short) occur and form in the heterocyclic ring. In the case of -N (O) and -S (O) groups, both enantiomers are included.
Erfindungsgemäß steht der Ausdruck„Heteroaryl" für heteroaromatische According to the invention, the term "heteroaryl" is heteroaromatic
Verbindungen, d. h. vollständig ungesättigte aromatische heterocyclische Compounds, d. H. fully unsaturated aromatic heterocyclic
Verbindungen, vorzugsweise für 5- bis 7-gliedrige Ringe mit 1 bis 4, vorzugsweise 1 oder 2 gleichen oder verschiedenen Heteroatomen, vorzugsweise O, S oder N. Compounds, preferably for 5- to 7-membered rings having 1 to 4, preferably 1 or 2 identical or different heteroatoms, preferably O, S or N.
Erfindungsgemäße Heteroaryle sind beispielsweise 1 H-Pyrrol-1 -yl; 1 H-Pyrrol-2-yl; 1 H- Pyrrol-3-yl; Furan-2-yl; Furan-3-yl; Thien-2-yl; Thien-3-yl, 1 H-lmidazol-1 -yl; 1 H- lmidazol-2-yl; 1 H-lmidazol-4-yl; 1 H-lmidazol-5-yl; 1 H-Pyrazol-1 -yl; 1 H-Pyrazol-3-yl; 1 H- Pyrazol-4-yl; 1 H-Pyrazol-5-yl, 1 H-1 ,2,3-Triazol-1 -yl, 1 H-1 ,2,3-Triazol-4-yl, 1 H-1 ,2,3- Triazol-5-yl, 2H-1 ,2,3-Triazol-2-yl, 2H-1 ,2,3-Triazol-4-yl, 1 H-1 ,2,4-Triazol-1 -yl, 1 H- 1 ,2,4-Triazol-3-yl, 4H-1 ,2,4-Triazol-4-yl, 1 ,2,4-Oxadiazol-3-yl, 1 ,2,4-Oxadiazol-5-yl, 1 ,3,4-Oxadiazol-2-yl, 1 ,2,3-Oxadiazol-4-yl, 1 ,2,3-Oxadiazol-5-yl, 1 ,2,5-Oxadiazol-3-yl, Azepinyl, Pyridin-2-yl, Pyridin-3-yl, Pyridin-4-yl, Pyrazin-2-yl, Pyrazin-3-yl, Pyrimidin-2- yl, Pyrimidin-4-yl, Pyrimidin-5-yl, Pyridazin-3-yl, Pyridazin-4-yl, 1 ,3,5-Triazin-2-yl, 1 ,2,4- Triazin-3-yl, 1 ,2,4-Triazin-5-yl, 1 ,2,4-Triazin-6-yl, 1 ,2,3-Triazin-4-yl, 1 ,2,3-Triazin-5-yl, 1 ,2,4-, 1 ,3,2-, 1 ,3,6- und 1 ,2,6-Oxazinyl, lsoxazol-3-yl, lsoxazol-4-yl, lsoxazol-5-yl, 1 ,3- Oxazol-2-yl, 1 ,3-Oxazol-4-yl, 1 ,3-Oxazol-5-yl, lsothiazol-3-yl, lsothiazol-4-yl, Isothiazol- 5-yl, 1 ,3-Thiazol-2-yl, 1 ,3-Thiazol-4-yl, 1 ,3-Thiazol-5-yl, Oxepinyl, Thiepinyl, 1 ,2,4- Triazolonyl und 1 ,2,4-Diazepinyl, 2H-1 ,2,3,4-Tetrazol-5-yl, 1 H-1 ,2,3,4-Tetrazol-5-yl, 1 ,2,3,4-Oxathazol-5-yl, 1 ,2,3,4-Thiatriazol-5-yl, 1 ,2,3,5-Oxatriazol-4-yl, 1 ,2,3,5- Thiatriazol-4-yl. Die erfindungsgemäßen Heteroarylgruppen können ferner mit einem oder mehreren, gleichen oder verschiedenen Resten substituiert sein. Sind zwei benachbarte Kohlenstoffatome Bestandteil eines weiteren aromatischen Rings, so handelt es sich um annellierte heteroaromatische Systeme, wie benzokondensierte oder mehrfach annellierte Heteroaromaten. Bevorzugt sind beispielsweise Chinoline (z. B. Chinolin-2-yl, Chinolin-3-yl, Chinolin-4-yl, Chinolin-5-yl, Chinolin-6-yl, Chinolin-7- yl, Chinolin-8-yl); Isochinoline (z. B. lsochinolin-1 -yl, lsochinolin-3-yl, lsochinolin-4-yl, lsochinolin-5-yl, lsochinolin-6-yl, lsochinolin-7-yl, lsochinolin-8-yl); Chinoxalin; Heteroaryls of the invention are, for example, 1H-pyrrol-1-yl; 1H-pyrrol-2-yl; 1H-pyrrol-3-yl; Furan-2-yl; Furan-3-yl; Thien-2-yl; Thien-3-yl, 1H-imidazole-1-yl; 1 H-imidazol-2-yl; 1 H -imidazol-4-yl; 1 H -imidazol-5-yl; 1H-pyrazole-1-yl; 1H-pyrazol-3-yl; 1H-pyrazol-4-yl; 1 H-pyrazol-5-yl, 1 H-1, 2,3-triazol-1-yl, 1 H-1, 2,3-triazol-4-yl, 1 H-1, 2,3-triazole 5-yl, 2H-1, 2,3-triazol-2-yl, 2H-1,2,3-triazol-4-yl, 1H-1, 2,4-triazol-1-yl, 1H- 1, 2,4-triazol-3-yl, 4H-1, 2,4-triazol-4-yl, 1, 2,4-oxadiazol-3-yl, 1, 2,4-oxadiazol-5-yl, 1, 3,4-oxadiazol-2-yl, 1, 2,3-oxadiazol-4-yl, 1, 2,3-oxadiazol-5-yl, 1, 2,5-oxadiazol-3-yl, azepinyl, Pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyrazine-2-yl, pyrazine-3-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyridazine 3-yl, pyridazin-4-yl, 1, 3,5-triazin-2-yl, 1, 2,4-triazin-3-yl, 1, 2,4-triazin-5-yl, 1, 2, 4-triazin-6-yl, 1, 2,3-triazin-4-yl, 1, 2,3-triazin-5-yl, 1, 2,4-, 1, 3, 3, 1, 3, 6- and 1, 2,6-oxazinyl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, 1,3-oxazol-2-yl, 1,3-oxazol-4-yl, 1 , 3-oxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1, 3-thiazol-2-yl, 1, 3-thiazol-4-yl, 1, 3 Thiazol-5-yl, oxepinyl, thiepinyl, 1, 2,4- Triazolonyl and 1,2,4-diazepinyl, 2H-1,2,3,4-tetrazol-5-yl, 1H-1,2,3,4-tetrazol-5-yl, 1, 2,3,4 -Oxathazol-5-yl, 1,2,3,4-thiatriazol-5-yl, 1, 2,3,5-oxatriazol-4-yl, 1, 2,3,5-thiatriazol-4-yl. The heteroaryl groups according to the invention may furthermore be substituted by one or more identical or different radicals. If two adjacent carbon atoms are part of another aromatic ring, they are fused heteroaromatic systems, such as benzo-fused or multiply fused heteroaromatics. Preference is given, for example, to quinolines (for example quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl ); Isoquinolines (e.g., isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl, isoquinolin-8-yl); quinoxaline;
Chinazolin; Cinnolin; 1 ,5-Naphthyridin; 1 ,6-Naphthyridin; 1 ,7-Naphthyridin; 1 ,8- Naphthyridin; 2,6-Naphthyridin; 2,7-Naphthyridin; Phthalazin; Pyridopyrazine; quinazoline; cinnoline; 1,5-naphthyridine; 1,6-naphthyridine; 1,7-naphthyridine; 1,8-naphthyridine; 2,6-naphthyridine; 2,7-naphthyridine; phthalazine; Pyridopyrazine;
Pyridopyrimidine; Pyridopyridazine; Pteridine; Pyrimidopyrimidine. Beispiele für Heteroaryl sind auch 5- oder 6-gliedrige benzokondensierte Ringe aus der Gruppe 1 H- lndol-1 -yl, 1 H-lndol-2-yl, 1 H-lndol-3-yl, 1 H-lndol-4-yl, 1 H-lndol-5-yl, 1 H-lndol-6-yl, 1 H- lndol-7-yl, 1 -Benzofuran-2-yl, 1 -Benzofuran-3-yl, 1 -Benzofuran-4-yl, 1 -Benzofuran-5-yl, 1 -Benzofuran-6-yl, 1 -Benzofuran-7-yl, 1 -Benzothiophen-2-yl, 1 -Benzothiophen-3-yl, 1 - Benzothiophen-4-yl, 1 -Benzothiophen-5-yl, 1 -Benzothiophen-6-yl, 1 -Benzothiophen-7- yl, 1 H-lndazol-1 -yl, 1 H-lndazol-3-yl, 1 H-lndazol-4-yl, 1 H-lndazol-5-yl, 1 H-lndazol-6-yl, 1 H-lndazol-7-yl, 2H-lndazol-2-yl, 2H-lndazol-3-yl, 2H-lndazol-4-yl, 2H-lndazol-5-yl, 2H- lndazol-6-yl, 2H-lndazol-7-yl, 2H-lsoindol-2-yl, 2H-lsoindol-1 -yl, 2H-lsoindol-3-yl, 2H- lsoindol-4-yl, 2H-lsoindol-5-yl, 2H-lsoindol-6-yl; 2H-lsoindol-7-yl, 1 H-Benzimidazol-1 -yl, 1 H-Benzimidazol-2-yl, 1 H-Benzimidazol-4-yl, 1 H-Benzimidazol-5-yl, 1 H-Benzimidazol- 6-yl, 1 H-Benzimidazol-7-yl, 1 ,3-Benzoxazol-2-yl, 1 ,3-Benzoxazol-4-yl, 1 ,3-Benzoxazol- 5-yl, 1 ,3-Benzoxazol-6-yl, 1 ,3-Benzoxazol-7-yl, 1 ,3-Benzthiazol-2-yl, 1 ,3-Benzthiazol-4- yl, 1 ,3-Benzthiazol-5-yl, 1 ,3-Benzthiazol-6-yl, 1 ,3-Benzthiazol-7-yl, 1 ,2-Benzisoxazol-3- yl, 1 ,2-Benzisoxazol-4-yl, 1 ,2-Benzisoxazol-5-yl, 1 ,2-Benzisoxazol-6-yl, 1 ,2- Benzisoxazol-7-yl, 1 ,2-Benzisothiazol-3-yl, 1 ,2-Benzisothiazol-4-yl, 1 ,2-Benzisothiazol- 5-yl, 1 ,2-Benzisothiazol-6-yl, 1 ,2-Benzisothiazol-7-yl. pyridopyrimidines; Pyridopyridazine; pteridines; Pyrimidopyrimidine. Examples of heteroaryl are also 5- or 6-membered benzo-fused rings from the group 1H-indol-1-yl, 1H-indol-2-yl, 1H-indol-3-yl, 1H-indole-4 yl, 1H-indol-5-yl, 1H-indol-6-yl, 1H-indol-7-yl, 1-benzofuran-2-yl, 1-benzofuran-3-yl, 1-benzofuran-4 -yl, 1-benzofuran-5-yl, 1-benzofuran-6-yl, 1-benzofuran-7-yl, 1-benzothiophen-2-yl, 1-benzothiophen-3-yl, 1-benzothiophen-4-yl , 1-benzothiophene-5-yl, 1-benzothiophene-6-yl, 1-benzothiophene-7-yl, 1-indazol-1-yl, 1-indazol-3-yl, 1-indazole-4-yl yl, 1H-indazol-5-yl, 1H-indazol-6-yl, 1H-indazol-7-yl, 2H-indazol-2-yl, 2H-indazol-3-yl, 2H-indazole-4 -yl, 2H-indazol-5-yl, 2H-indazol-6-yl, 2H-indazol-7-yl, 2H-isoindol-2-yl, 2H-isoindol-1-yl, 2H-isoindol-3-yl , 2H-isoindol-4-yl, 2H-isoindol-5-yl, 2H-isoindol-6-yl; 2H-isoindol-7-yl, 1H-benzimidazol-1-yl, 1H-benzimidazol-2-yl, 1H-benzimidazol-4-yl, 1H-benzimidazol-5-yl, 1H-benzimidazole-6 -yl, 1H-benzimidazol-7-yl, 1, 3-benzoxazol-2-yl, 1,3-benzoxazol-4-yl, 1,3-benzoxazol-5-yl, 1,3-benzoxazole-6 yl, 1,3-benzoxazol-7-yl, 1,3-benzthiazol-2-yl, 1,3-benzthiazol-4-yl, 1,3-benzthiazol-5-yl, 1,3-benzthiazole-6 yl, 1, 3-benzthiazol-7-yl, 1,2-benzisoxazol-3-yl, 1,2-benzisoxazol-4-yl, 1,2-benzisoxazol-5-yl, 1,2-benzisoxazole-6 yl, 1, 2-benzisoxazol-7-yl, 1,2-benzisothiazol-3-yl, 1,2-benzisothiazol-4-yl, 1,2-benzisothiazol-5-yl, 1,2-benzisothiazole-6 yl, 1,2-benzisothiazol-7-yl.
Die Bezeichnung "Halogen" bedeutet beispielsweise Fluor, Chlor, Brom oder lod. Wird die Bezeichnung für einen Rest verwendet, dann bedeutet "Halogen" beispielsweise ein Fluor-, Chlor-, Brom- oder lodatom. Erfindungsgemäß bedeutet„Alkyl" einen geradkettigen oder verzweigten offenkettigen, gesättigten Kohlenwasserstoffrest, der gegebenenfalls ein- oder mehrfach substituiert ist und im letzteren Falle als„substituiertes Alkyl" bezeichnet wird. Bevorzugte The term "halogen" means, for example, fluorine, chlorine, bromine or iodine. When the term for a group is used, "halogen" means, for example, a fluorine, chlorine, bromine or iodine atom. According to the invention, "alkyl" means a straight-chain or branched, open-chain, saturated hydrocarbon radical which is optionally monosubstituted or polysubstituted and is referred to in the latter case as "substituted alkyl". preferred
Substituenten sind Halogenatome, Alkoxy-, Haloalkoxy-, Cyano-, Alkylthio, Substituents are halogen atoms, alkoxy, haloalkoxy, cyano, alkylthio,
Haloalkylthio-, Amino- oder Nitrogruppen, besonders bevorzugt sind Methoxy, Methyl, Fluoralkyl, Cyano, Nitro, Fluor, Chlor, Brom oder lod. Die Vorsilbe„Bis" schließt auch die Kombination unterschiedlicher Alkylreste ein, z. B. Methyl(Ethyl) oder Haloalkylthio, amino or nitro groups, particularly preferred are methoxy, methyl, fluoroalkyl, cyano, nitro, fluorine, chlorine, bromine or iodine. The prefix "bis" also includes the combination of different alkyl radicals, for example, methyl (ethyl) or
Ethyl(Methyl). „Haloalkyl",„-alkenyl" und„-alkinyl" bedeuten durch gleiche oder verschiedene Ethyl (methyl). "Haloalkyl", "alkenyl" and "alkynyl" mean the same or different
Halogenatome, teilweise oder vollständig substituiertes Alkyl, Alkenyl bzw. Alkinyl, z.B. Monohaloalkyl (= Monohalogenalkyl) wie z. B. CH2CH2CI, CH2CH2Br, CHCICH3, CH2CI, CH2F; Perhaloalkyl wie z. B. CCI3, CCIF2, CFCI2,CF2CCIF2, CF2CCIFCF3; Halogen atoms, partially or fully substituted alkyl, alkenyl or alkynyl, for example monohaloalkyl (= monohaloalkyl) such. CH 2 CH 2 Cl, CH 2 CH 2 Br, CHCICH 3 , CH 2 Cl, CH 2 F; Perhaloalkyl such. CCI 3 , CCIF 2 , CFCI 2 , CF 2 CCIF 2 , CF 2 CCIFCF 3 ;
Polyhaloalkyl wie z. B. CH2CHFCI, CF2CCIFH, CF2CBrFH, CH2CF3; Der Begriff Perhaloalkyl umfasst dabei auch den Begriff Perfluoralkyl. Polyhaloalkyl such. CH 2 CHFCI, CF 2 CCIFH, CF 2 CBrFH, CH 2 CF 3 ; The term perhaloalkyl also encompasses the term perfluoroalkyl.
Teilfluoriertes Alkyl bedeutet einen geradkettigen oder verzweigten, gesättigten Partially fluorinated alkyl means a straight-chain or branched, saturated
Kohlenwasserstoff, der einfach oder mehrfach durch Fluor substituiert ist, wobei sich die entsprechenden Fluoratome als Substituenten an einem oder mehreren Hydrocarbon which is mono- or polysubstituted by fluorine, wherein the corresponding fluorine atoms as substituents on one or more
verschiedenen Kohlenstoffatomen der geradkettigen oder verzweigten different carbon atoms of the straight-chain or branched
Kohlenwasserstoffkette befinden können, wie z. B. CHFCH3, CH2CH2F, CH2CH2CF3, CHF2, CH2F, CHFCF2CF3 Hydrocarbon chain can be located, such as. B. CHFCH3, CH 2 CH 2 F, CH 2 CH 2 CF 3, CHF 2, CH 2 F, CF 3 CHFCF 2
Teilfluoriertes Haloalkyl bedeutet einen geradkettigen oder verzweigten, gesättigten Kohlenwasserstoff, der durch verschiedenene Halogenatomen mit mindestens einem Fluoratom substituiert ist, wobei alle anderen gegebenenfalls vorhandenen Partially fluorinated haloalkyl means a straight-chain or branched, saturated hydrocarbon which is substituted by various halogen atoms having at least one fluorine atom, all other optionally present
Halogenatome ausgewählt sind aus der Gruppe Fluor, Chlor oder Brom, lod. Die entsprechenden Halogenatome können sich dabei als Substituenten an einem oder mehreren verschiedenen Kohlenstoffatomen der geradkettigen oder verzweigten Kohlenwasserstoffkette befinden. Teilfluoriertes Haloalkyl schließt auch die Halogen atoms are selected from the group fluorine, chlorine or bromine, iodine. The corresponding halogen atoms may be present as substituents on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain. Partially fluorinated haloalkyl also includes the
vollständige Substitution der geradkettigen oder verzweigten Kette durch Halogen unter Beteiligung von mindestens einem Fluoratom ein. Haloalkoxy ist z.B. OCF3, OCHF2, OCH2F, OCF2CF3, OCH2CF3 und OCH2CH2CI; complete substitution of the straight-chain or branched chain by halogen with the participation of at least one fluorine atom. Haloalkoxy is eg OCF 3 , OCHF 2 , OCH 2 F, OCF 2 CF 3 , OCH 2 CF 3 and OCH 2 CH 2 Cl;
Entsprechendes gilt für Haloalkenyl und andere durch Halogen substituierten Reste. The same applies to haloalkenyl and other halogen-substituted radicals.
Der hier beispielhaft genannte Ausdruck "(Ci-C4)-Alkyl" bedeutet eine The term "(C 1 -C 4 ) -alkyl" given here by way of example means a
Kurzschreibweise für geradkettiges oder verzweigtes Alkyl mit einem bis 4 Short notation for straight-chain or branched alkyl having one to four
Kohlenstoffatomen entsprechend der Bereichsangabe für C-Atome, d. h. umfasst die Reste Methyl, Ethyl, 1 -Propyl, 2-Propyl, 1 -Butyl, 2-Butyl, 2-Methylpropyl oder tert-Butyl. Allgemeine Alkylreste mit einem größeren angegebenen Bereich von C-Atomen, z. B. "(Ci-C6)-Alkyl", umfassen entsprechend auch geradkettige oder verzweigte Alkylreste mit einer größeren Zahl von C-Atomen, d. h. gemäß Beispiel auch die Alkylreste mit 5 und 6 C-Atomen.  Carbon atoms corresponding to the range for C atoms, d. H. includes the radicals methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl. General alkyl radicals having a larger specified range of carbon atoms, eg. As "(Ci-C6) alkyl", accordingly also include straight-chain or branched alkyl radicals having a larger number of C atoms, d. H. according to example, the alkyl radicals with 5 and 6 carbon atoms.
Wenn nicht speziell angegeben, sind bei den Kohlenwasserstoffresten wie Alkyl-, Alkenyl- und Alkinylresten, auch in zusammengesetzten Resten, die niederen Unless specifically stated, the hydrocarbon radicals such as alkyl, alkenyl and alkynyl radicals, even in assembled radicals, are lower
Kohlenstoffgerüste, z.B. mit 1 bis 6 C-Atomen bzw. bei ungesättigten Gruppen mit 2 bis 6 C-Atomen, bevorzugt. Alkylreste, auch in den zusammengesetzten Resten wie Alkoxy, Haloalkyl usw., bedeuten z.B. Methyl, Ethyl, n- oder i-Propyl, n-, i-, t- oder 2-Butyl, Pentyle, Hexyle, wie n-Hexyl, i-Hexyl und 1 ,3-Dimethylbutyl, Heptyle, wie n-Heptyl, 1 -Methylhexyl und 1 ,4-Dimethylpentyl; Alkenyl- und Alkinylreste haben die Bedeutung der den Alkylresten entsprechenden möglichen ungesättigten Reste, wobei mindestens eine Doppelbindung bzw. Dreifachbindung enthalten ist. Bevorzugt sind Reste mit einer Doppelbindung bzw. Dreifachbindung. Carbon skeletons, e.g. with 1 to 6 C atoms or with unsaturated groups having 2 to 6 C atoms, preferred. Alkyl radicals, also in the assembled radicals such as alkoxy, haloalkyl, etc., mean e.g. Methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i-hexyl and 1,3-dimethylbutyl, heptyls, such as n-heptyl, 1-methylhexyl and 1, 4-dimethylpentyl; Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals, wherein at least one double bond or triple bond is contained. Preference is given to radicals having a double bond or triple bond.
Der Begriff„Alkenyl" schließt insbesondere auch geradkettige oder verzweigte offenkettige Kohlenwasserstoffreste mit mehr als einer Doppelbindung ein, wie 1 ,3- Butadienyl und 1 ,4-Pentadienyl, aber auch Allenyl- oder Kumulenyl-reste mit einer bzw. mehreren kumulierten Doppelbindungen, wie beispielsweise Allenyl (1 ,2- Propadienyl), 1 ,2-Butadienyl und 1 ,2,3-Pentatrienyl. Alkenyl bedeutet z.B. Vinyl, welches ggf. durch weitere Alkylreste substituiert sein kann, z B. (aber nicht In particular, the term "alkenyl" also includes straight-chain or branched open-chain hydrocarbon radicals having more than one double bond, such as 1,3-butadienyl and 1,4-pentadienyl, but also allenyl or cumulenyl radicals having one or more cumulative double bonds, such as For example, allenyl (1,2-propadienyl), 1,2-butadienyl and 1,2,3-pentatrienyl.Alkenyl means, for example, vinyl, which may optionally be substituted by further alkyl radicals, for example (but not
beschränkt auf) (C2-C6)-Alkenyl wie Ethenyl, 1 -Propenyl, 2-Propenyl, 1 -Methylethenyl, 1 -Butenyl, 2-Butenyl, 3-Butenyl, 1 -Methyl-1 -propenyl, 2-Methyl-1 -propenyl, 1 -Methyl-2- propenyl, 2-Methyl-2-propenyl, 1 -Pentenyl, 2-Pentenyl, 3-Pentenyl, 4-Pentenyl, 1 - Methyl-1 -butenyl, 2-Methyl-1 -butenyl, 3-Methyl-1 -butenyl, 1 -Methyl-2-butenyl, 2- Methyl-2-butenyl, 3-Methyl-2-butenyl, 1 -Methyl-3-butenyl, 2-Methyl-3-butenyl, 3- Methyl-3-butenyl, 1 ,1 -Dimethyl-2-propenyl, 1 ,2-Dimethyl-1 -propenyl, 1 ,2-Dimethyl-2- propenyl, 1 -Ethyl-1 -propenyl, 1 -Ethyl-2-propenyl, 1 -Hexenyl, 2-Hexenyl, 3-Hexenyl, 4- Hexenyl, 5-Hexenyl, 1 -Methyl-1 -pentenyl, 2-Methyl-1 -pentenyl, 3-Methyl-1 -pentenyl, 4- Methyl-1 -pentenyl, 1 -Methyl-2-pentenyl, 2-Methyl-2-pentenyl, 3-Methyl-2-pentenyl, 4- Methyl-2-pentenyl, 1 -Methyl-3-pentenyl, 2-Methyl-3-pentenyl, 3-Methyl-3-pentenyl, 4- Methyl-3-pentenyl, 1 -Methyl-4-pentenyl, 2-Methyl-4-pentenyl, 3-Methyl-4-pentenyl, 4- Methyl-4-pentenyl, 1 ,1 -Dimethyl-2-butenyl, 1 ,1 -Dimethyl-3-butenyl, 1 ,2-Dimethyl-1 - butenyl, 1 ,2-Dimethyl-2-butenyl, 1 ,2-Dimethyl-3-butenyl, 1 ,3-Dimethyl-1 -butenyl, 1 ,3- Dimethyl-2-butenyl, 1 ,3-Dimethyl-3-butenyl, 2,2-Dimethyl-3-butenyl, 2,3-Dimethyl-1 - butenyl, 2,3-Dimethyl-2-butenyl, 2,3-Dimethyl-3-butenyl, 3,3-Dimethyl-1 -butenyl, 3,3- Dimethyl-2-butenyl, 1 -Ethyl-1 -butenyl, 1 -Ethyl-2-butenyl, 1 -Ethyl-3-butenyl, 2-Ethyl-1 - butenyl, 2-Ethyl-2-butenyl, 2-Ethyl-3-butenyl, 1 ,1 ,2-Trimethyl-2-propenyl, 1 -Ethyl-1 - methyl-2-propenyl, 1 -Ethyl-2-methyl-1 -propenyl und 1 -Ethyl-2-methyl-2-propenyl. Der Begriff„Alkinyl" schließt insbesondere auch geradkettige oder verzweigte offenkettige Kohlenwasserstoffreste mit mehr als einer Dreifachbindung oder auch mit einer oder mehreren Dreifachbindungen und einer oder mehreren Doppelbindungen ein, wie beispielsweise 1 ,3-Butatrienyl bzw. 3-Penten-1 -in-1 -yl. (C2-C6)-Alkinyl bedeutet z.B. Ethinyl, 1 -Propinyl, 2-Propinyl, 1 -Butinyl, 2-Butinyl, 3-Butinyl, 1 -Methyl-2- propinyl, 1 -Pentinyl, 2-Pentinyl, 3-Pentinyl, 4-Pentinyl, 1 -Methyl-2-butinyl, 1 -Methyl-3- butinyl, 2-Methyl-3-butinyl, 3-Methyl-1 -butinyl, 1 ,1 -Dimethyl-2-propinyl, 1 -Ethyl-2- propinyl, 1 -Hexinyl, 2-Hexinyl, 3-Hexinyl, 4-Hexinyl, 5-Hexinyl, 1 -Methyl-2-pentinyl, 1 - Methyl-3-pentinyl, 1 -Methyl-4-pentinyl, 2-Methyl-3-pentinyl, 2-Methyl-4-pentinyl, 3- Methyl-1 -pentinyl, 3-Methyl-4-pentinyl, 4-Me-"thyl-1 -pentinyl, 4-Methyl-2-pentinyl, 1 ,1 - Di-methyl-2-butinyl, 1 ,1 -Dimethyl-3-butinyl, 1 ,2-Di->methyl-3-butinyl, 2,2-Dimethyl-3- butinyl, 3,3-Dimethyl-1 -butinyl, 1 -Ethyl-2-butinyl, 1 -Ethyl-3-butinyl, 2-Ethyl-3-butinyl und 1 -Ethyl-1 -methyl-2-propinyl. limited to) (C 2 -C 6) alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1 -propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl , 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3 - Methyl 3-butenyl, 1, 1-dimethyl-2-propenyl, 1, 2-dimethyl-1-propenyl, 1, 2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2- propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl 1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3 pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1, 1-dimethyl-2-butenyl, 1, 1-dimethyl-3-butenyl, 1, 2-dimethyl-1-butenyl, 1, 2-dimethyl-2-butenyl, 1, 2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1, 3-dimethyl-2-butenyl, 1, 3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1 - Ethyl 2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl , 2-ethyl-3-butenyl, 1, 1, 2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2 -methyl-2-propenyl. The term "alkynyl" in particular also includes straight-chain or branched open-chain hydrocarbon radicals having more than one triple bond or else having one or more triple bonds and one or more double bonds, for example 1,3-butatrienyl or 3-penten-1-yn-1 -yl. (C 2 -C 6) -alkynyl is, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4 pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2 -pentinyl, 1,1-di-methyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-di-> methyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3, 3-dimethyl-1-butynyl, 1 - Ethyl 2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl.
Der Begriff„Cycloalkyl" bedeutet ein carbocyclisches, gesättigtes Ringsystem mit vorzugsweise 3-8 Ring-C-Atomen, z.B. Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl, das gegebenenfalls weiter substituiert ist, bevorzugt durch Wasserstoff, Alkyl, Alkoxy, Cyano, Nitro, Alkylthio, Haloalkylthio, Halogen, Alkenyl, Alkinyl, The term "cycloalkyl" means a carbocyclic, saturated ring system preferably having 3-8 ring C atoms, eg cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, which is optionally further substituted, preferably by hydrogen, alkyl, alkoxy, cyano, nitro, alkylthio , Haloalkylthio, halogen, alkenyl, alkynyl,
Haloalkyl, AMino, Alkylamino, Bisalkylamino, Alkocycarbonyl, Hydroxycarbonyl, Arylalkoxycarbonyl, Aminocarbonyl, Alkylaminocarbonyl, Cycloalkylaminocarbonyl . Im Falle von gegebenenfalls substituiertem Cycloalkyl werden cyclische Systeme mit Substituenten umfasst, wobei auch Substituenten mit einer Doppelbindung am Haloalkyl, amino, alkylamino, bisalkylamino, alkocycarbonyl, hydroxycarbonyl, arylalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, cycloalkylaminocarbonyl. in the Traps of optionally substituted cycloalkyl include cyclic systems having substituents wherein substituents having a double bond on the
Cycloalkylrest, z. B. eine Alkylidengruppe wie Methyliden, umfasst sind. Im Falle von gegebenenfalls substituiertem Cycloalkyl werden auch mehrcyclische aliphatische Systeme umfasst, wie beispielsweise Bicyclo[1 .1 .0]butan-1 -yl, Bicyclo[1 .1 .0]butan-2-yl, Bicyclo[2.1 .0]pentan-1 -yl, Bicyclo[1 .1 .1 ]pentan-1 -yl, Bicyclo[2.1 .0]pentan-2-yl, Cycloalkyl, z. As an alkylidene group such as methylidene, are included. In the case of optionally substituted cycloalkyl, it also encompasses polycyclic aliphatic systems such as, for example, bicyclo [1, 1] -butan-1-yl, bicyclo [1, 1] -butan-2-yl, bicyclo [2.1.0] pentane 1 -yl, bicyclo [1 .1 .1] pentan-1-yl, bicyclo [2.1.0] pentan-2-yl,
Bicyclo[2.1 .0]pentan-5-yl, Bicyclo[2.1 .1]hexyl, Bicyclo[2.2.1]hept-2-yl, Bicyclo [2.1.0] pentan-5-yl, bicyclo [2.1.1] hexyl, bicyclo [2.2.1] hept-2-yl,
Bicyclo[2.2.2]octan-2-yl, Bicyclo[3.2.1 ]octan-2-yl, Bicyclo[3.2.2]nonan-2-yl, Adamantan- 1 -yl und Adamantan-2-yl, aber auch Systeme wie z. B. 1 ,1 '-Bi(cyclopropyl)-1 -yl, 1 ,1 '- Bi(cyclopropyl)-2-yl. Der Ausdruck "(C3-C7)-Cycloalkyl" bedeutet eine Bicyclo [2.2.2] octan-2-yl, bicyclo [3.2.1] octan-2-yl, bicyclo [3.2.2] nonan-2-yl, adamantan-1-yl and adamantan-2-yl, but also Systems such. B. 1, 1 '-Bi (cyclopropyl) -1-yl, 1, 1' - Bi (cyclopropyl) -2-yl. The term "(C 3 -C 7) -cycloalkyl" means a
Kurzschreibweise für Cycloalkyl mit drei bis 7 Kohlenstoffatomen entsprechend der Bereichsangabe für C-Atome.  Abbreviation for cycloalkyl having three to 7 carbon atoms corresponding to the range for C atoms.
Im Falle von substituiertem Cycloalkyl werden auch spirocyclische aliphatische In the case of substituted cycloalkyl are also spirocyclic aliphatic
Systeme umfasst, wie beispielsweise Spiro[2.2]pent-1 -yl, Spiro[2.3]hex-1 -yl, Systems such as spiro [2.2] pent-1-yl, spiro [2.3] hex-1-yl,
Spiro[2.3]hex-4-yl, 3-Spiro[2.3]hex-5-yl, Spiro[3.3]hept-1 -yl, Spiro[3.3]hept-2-yl. Spiro [2.3] hex-4-yl, 3-spiro [2.3] hex-5-yl, spiro [3.3] hept-1-yl, spiro [3.3] hept-2-yl.
„Cycloalkenyl" bedeutet ein carbocyclisches, nicht aromatisches, partiell ungesättigtes Ringsystem mit vorzugsweise 4-8 C-Atomen, z.B. 1 -Cyclobutenyl, 2-Cyclobutenyl, 1 - Cyclopentenyl, 2-Cyclopentenyl, 3-Cyclopentenyl, oder 1 -Cyclohexenyl, 2-"Cycloalkenyl" means a carbocyclic, non-aromatic, partially unsaturated ring system preferably having 4-8 C atoms, for example 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2-
Cyclohexenyl, 3-Cyclohexenyl, 1 ,3-Cyclohexadienyl oder 1 ,4-Cyclohexadienyl, wobei auch Substituenten mit einer Doppelbindung am Cycloalkenylrest, z. B. eine Cyclohexenyl, 3-cyclohexenyl, 1, 3-cyclohexadienyl or 1, 4-cyclohexadienyl, wherein also substituents having a double bond on the cycloalkenyl, z. Legs
Alkylidengruppe wie Methyliden, umfasst sind. Im Falle von gegebenenfalls Alkylidene group such as methylidene, are included. In case of if necessary
substituiertem Cycloalkenyl gelten die Erläuterungen für substituiertes Cycloalkyl entsprechend. Substituted cycloalkenyl the explanations for substituted cycloalkyl apply accordingly.
Der Begriff„AI kyliden", z. B. auch in der Form (Ci-Cio)-Alkyliden, bedeutet den Rest eines geradkettigen oder verzweigten offenkettigen Kohlenwasserstoffrests, der über eine Zweifachbindung gebunden ist. Als Bindungsstelle für Alkyliden kommen naturgemäß nur Positionen am Grundkörper in Frage, an denen zwei H-Atome durch die Doppelbindung ersetzt werden können; Reste sind z. B. =CH2, =CH-CH3, The term "alkylidene", for example also in the form (C 1 -C 10) -alkylidene, means the radical of a straight-chain or branched open-chain hydrocarbon radical which is bonded via a double bond.As a binding site for alkylidene, only positions on the main body naturally occur in question, in which two H atoms can be replaced by the double bond, radicals are, for example = CH 2, = CH-CH 3,
=C(CH3)-CH3, =C(CH3)-C2H5 oder =C(C2H5)-C2H5. Cycloalkyliden bedeutet ein carbocyclischer Rest, der über eine Zweifachbindung gebunden ist. Wenn die Verbindungen durch Wasserstoffverschiebung Tautomere bilden können, welche strukturell formal nicht durch die Formel (I) erfasst würden, so sind diese Tautomere gleichwohl von der Definition der erfindungsgemäßen Verbindungen der Formel (I) umfasst, sofern nicht ein bestimmtes Tautomer Gegenstand der = C (CH 3) -CH 3, = C (CH 3) -C 2 H 5 or = C (C 2 H 5) C 2 H5. Cycloalkylidene means a carbocyclic radical which is bonded via a double bond. If the compounds can form tautomers by hydrogen shift which would not be structurally formally recognized by the formula (I), these tautomers are nevertheless encompassed by the definition of the compounds of the formula (I) according to the invention, unless a particular tautomer is the subject of
Betrachtung ist. So können beispielsweise viele Carbonylverbindungen sowohl in der Ketoform wie auch in der Enolform vorliegen, wobei beide Formen durch die Definition der Verbindung der Formel (I) umfasst werden. Contemplation is. For example, many carbonyl compounds may be present in both the keto form and the enol form, both of which are encompassed by the definition of the compound of formula (I).
Die Verbindungen der allgemeinen Formel (I) können je nach Art und Verknüpfung der Substituenten als Stereoisomere vorliegen. Die durch ihre spezifische Raumform definierten möglichen Stereoisomere, wie Enantiomere, Diastereomere, Z- und E- Isomere sind alle von der Formel (I) umfasst. Sind beispielsweise eine oder mehrere Alkenylgruppen vorhanden, so können Diastereomere (Z- und E-Isomere) auftreten. Sind beispielsweise ein oder mehrere asymmetrische Kohlenstoffatome vorhanden, so können Enantiomere und Diastereomere auftreten. Stereoisomere lassen sich aus den bei der Herstellung anfallenden Gemischen nach üblichen Trennmethoden erhalten. Die chromatographische Trennung kann sowohl im analytischen Maßstab zur Depending on the nature and linkage of the substituents, the compounds of the general formula (I) can exist as stereoisomers. The possible stereoisomers defined by their specific spatial form, such as enantiomers, diastereomers, Z and E isomers, are all encompassed by the formula (I). If, for example, one or more alkenyl groups are present, diastereomers (Z and E isomers) can occur. For example, if one or more asymmetric carbon atoms are present, enantiomers and diastereomers may occur. Stereoisomers can be obtained from the resulting mixtures in the preparation by conventional separation methods. The chromatographic separation can be used both on an analytical scale for
Feststellung des Enantiomerenüberschusses bzw. des Diastereomerenüberschusses, wie auch im präparativen Maßstab zur Herstellung von Prüfmustern für die biologische Ausprüfung erfolgen. Ebenso können Stereoisomere durch Einsatz stereoselektiver Reaktionen unter Verwendung optisch aktiver Ausgangs- und/oder Hilfsstoffe selektiv hergestellt werden. Die Erfindung betrifft somit auch alle Stereoisomeren, die von der allgemeinen Formel (I) umfasst, jedoch nicht mit ihrer spezifischen Stereoform angegeben sind, sowie deren Gemische. Determination of the enantiomeric excess or of the diastereomeric excess, as also carried out on a preparative scale for the production of test samples for biological testing. Similarly, stereoisomers can be selectively prepared by using stereoselective reactions using optically active sources and / or adjuvants. The invention thus also relates to all stereoisomers which comprises the general formula (I) but are not specified with their specific stereoform, and mixtures thereof.
Synthese von substituierten Heteroarylcarbonsäurehydraziden: Synthesis of substituted heteroarylcarboxylic acid hydrazides:
Substituierte Heteroarylcarbonsaurehydrazide der allgemeinen Formel (I) können nach bekannten Verfahren hergestellt werden (vgl. Tetrahedron 2003, 59, 7733; J. Substituted heteroarylcarboxylic acid hydrazides of the general formula (I) can be prepared by known processes (see Tetrahedron 2003, 59, 7733;
Organomet. Chem. 2001 , 617; J. Org. Chem. 1962, 27, 2640; IT2000MI0292; J. Organomet. Chem. 2001, 617; J. Org. Chem. 1962, 27, 2640; IT2000MI0292; J.
Heterocyclic Chem. 1981 , 18, 319). Verschiedene literaturbekannte Herstellungswege zum Aufbau der Kernstruktur wurden verwendet und teilweise optimiert (siehe Schema 1 ). Ausgewählte detaillierte Synthesebeispiele sind im nächsten Abschnitt aufgeführt. Die eingesetzten und untersuchten Syntheserouten zur Herstellung von substituierten Heteroarylcarbonsäurehydraziden gehen dabei von kommerziell erhältlichen oder anhand von literaturbeschriebenen Syntheserouten leicht herstellbaren Heterocyclic Chem. 1981, 18, 319). Various manufacturing routes known to build the core structure were used and partially optimized (see Scheme 1). Selected detailed synthesis examples are listed in the next section. The synthesis routes employed and investigated for the preparation of substituted heteroarylcarboxylic acid hydrazides are based on commercially available or easily synthesized synthetic routes
Heteroarylcarbonsäuren und Heteroarylcarbonsäurechloriden aus. Die betreffende gegebenenfalls weiter substituierte Heteroarylcarbonsäure wird dabei mit Hilfe eines geeigneten Chlorierungsmittels (z. B. Oxalylchlorid oder Thionylchlorid) in einem aprotischen Lösemittel (z.B. Toluol) in das entsprechende Heteroarylcarbonsäuren and Heteroarylcarbonsäurechloriden. The optionally further substituted heteroarylcarboxylic acid in question is converted into the corresponding by means of a suitable chlorinating agent (for example oxalyl chloride or thionyl chloride) in an aprotic solvent (for example toluene)
Heteroarylcarbonsäurechlorid überführt, falls dieses nicht kommerziell verfügbar ist, und dieses danach mit einem entsprechend 1 ,1 '-disubstituierten Hydrazin unter Verwendung einer geeigneten Base (z.B. Triethylamin (EtsN)), Di-iso-Propylethylamin) in einem geeigneten polar-aprotischen Lösemittel (z.B. Tetrahydrofuran (THF) oder Dichlormethan (DCM)) zu einem Heteroarylcarbonsaurehydrazid (A) umgesetzt. Das gegebenenfalls weiter substituierte Heteroarylcarbonsaurehydrazid (A) kann auch über eine direkte, durch geeignete Reagenzien (z. B. 1 -Hydroxybenzotriazole (HOBt), N-(3- Dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (EDC) oder 2,4,6-Tripropyl- 1 ,3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxid (T3P) zusammen mit einer geeigneten Base wie z.B. Triethylamin oder Di-iso-Propylethylamin) vermittelte Kupplung einer gegebenenfalls weiter substituierten Heteroarylcarbonsäure mit einem entsprechend 1 ,1 '-disubstituierten Hydrazin in einem geeigneten polar-aprotischen Lösemittel (z.B. Dichlormethan, Acetonitril oder Tetrahydrofuran) hergestellt werden. Im nächsten Heteroarylcarbonsäurechlorid transferred, if this is not commercially available, and this then with a corresponding 1, 1 'disubstituted hydrazine using a suitable base (eg triethylamine (EtsN)), di-iso-propylethylamine) in a suitable polar aprotic solvent ( For example, tetrahydrofuran (THF) or dichloromethane (DCM)) to a Heteroarylcarbonsaurehydrazid (A) implemented. The optionally further substituted heteroarylcarboxylic acid hydrazide (A) can also be prepared by a direct reaction with suitable reagents (eg 1-hydroxybenzotriazoles (HOBt), N- (3-dimethylaminopropyl) -N'-ethylcarbodiimide hydrochloride (EDC) or 2,4, 6-Tripropyl- 1, 3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide (T3P) together with a suitable base such as triethylamine or di-iso-propylethylamine) mediated coupling of an optionally further substituted heteroarylcarboxylic with a corresponding 1, 1 'disubstituted hydrazine in a suitable polar aprotic solvent (eg dichloromethane, acetonitrile or tetrahydrofuran) are prepared. In the next
Schritt wird das gegebenenfalls weiter substituierte Heteroarylcarbonsäurehydrazid (A) unter Verwendung eines entsprechend substituierten Arylalkylhalogenids oder Step is the optionally further substituted heteroarylcarboxylic (A) using an appropriately substituted arylalkyl halide or
Heteroarylalkylhalogenids und einer geeigneten Base (z.B. Natriumhydrid oder Heteroarylalkyl halide and a suitable base (e.g., sodium hydride or
Triethylamin (EtsN)) in einem geeigneten Lösemittel (z.B. Tetrahydrofuran, N,N- Dimethylformamid (DMF) oder Dichlormethan) in ein substituiertes Triethylamine (EtsN)) in a suitable solvent (e.g., tetrahydrofuran, N, N-dimethylformamide (DMF) or dichloromethane) into a substituted solvent
Heteroarylcarbonsäurehydrazid (I) überführt (Schema 1 ). R1, R3, R4, R5 und R6 sowie A1, A2, A3, A4, A5, X1, X2, X3 und Y haben die zuvor definierten Bedeutungen und W steht beispielhaft, aber nicht einschränkend, im folgenden Schema 1 für Sauerstoff. Heteroarylcarbonsäurehydrazid (I) transferred (Scheme 1). R 1 , R 3 , R 4 , R 5 and R 6 and A 1 , A 2 , A 3 , A 4 , A 5 , X 1 , X 2 , X 3 and Y have the meanings defined above and W is an example, but not limiting, in the following Scheme 1 for oxygen.
Schema 1 . Scheme 1.
Substituierte Heteroarylcarbonsäurehydrazide der allgemeinen Formel (I) können alternativ auch über die Reduktion von Hydrazonen (B) hergestellt werden, sofern der Rest R6 für Wasserstoff steht. Im Verlauf dieser Synthesesequenz wird ein Substituted heteroarylcarboxylic acid hydrazides of the general formula (I) can alternatively also be prepared via the reduction of hydrazones (B), provided that the radical R 6 is hydrogen. In the course of this synthesis sequence becomes
entsprechend substituierter Aldehyd oder ein entsprechend substituiertes Keton mit einem entsprechend 1 ,1 '-disubstituierten Hydrazin zur Hydrazonzwischenstufe (B) umgesetzt, danach mit Hilfe eines geeigneten Reagens (z. B. Triethylsilan, BH3, Natnumcyanoborhydrid, Natriumborhydrid oder Wasserstoff auf Palladium/Kohle) in einem geeigneten Lösemittel in die entsprechende Hydrazinzwischenstufe (C) überführt, die im abschließenden Reaktionsschritt mit einem gegebenenfalls weiter substituierten Heteroarylcarbonsäurechlorid in einem geeigneten polar-aprotischen Lösemittel (z. B. Tetrahydrofuran oder Dichlormethan in ein substituiertes correspondingly substituted aldehyde or a correspondingly substituted ketone with a corresponding 1, 1 '-disubstituted hydrazine to Hydrazonzwischenstufe (B) reacted, then with the aid of a suitable reagent (eg., Triethylsilan, BH3, Natnumcyanoborhydrid, sodium borohydride or hydrogen on palladium / carbon) in a suitable solvent in the corresponding hydrazine intermediate (C), which in the final reaction step with an optionally further substituted heteroarylcarbonyl chloride in a suitable polar aprotic solvent (eg., Tetrahydrofuran or dichloromethane in a substituted
Heteroarylcarbonsäure-hydrazid (I) überführt wird (Schema 2). R1, R3, R4 und R5 sowie A1, A2, A3, A4, A5, X1, X2, X3 und Y haben die zuvor definierten Bedeutungen und W steht beispielhaft, aber nicht einschränkend, im unten aufgeführten Schema 2 für Sauerstoff. Heteroarylcarbonsäure hydrazide (I) is transferred (Scheme 2). R 1 , R 3 , R 4 and R 5 and A 1 , A 2 , A 3 , A 4 , A 5 , X 1 , X 2 , X 3 and Y have the meanings defined above and W is exemplified, but not limiting in scheme 2 below for oxygen.
Schema 2.  Scheme 2.
Am zweiten Hydrazidstickstoff (NR3R4) unsymmetrisch substituierte Heteroaryl- carbonsäurehydrazide (I) können auch unter Verwendung von tert-Butyl-1 - methylhydrazincarboxylat hergestellt werden (Schema 3). Die betreffende Unsymmetrically substituted heteroarylcarboxylic acid hydrazides (I) can also be prepared on the second hydrazide nitrogen (NR 3 R 4 ) using tert-butyl 1-methylhydrazinecarboxylate (Scheme 3). The person in question
gegebenenfalls weiter substituierte Heteroarylcarbonsäure wird dabei mit Hilfe eines geeigneten Chlorierungsmittels (z. B. Oxalylchlorid oder Thionylchlorid) in einem aprotischen Lösemittel (z.B. Toluol) in das entsprechende Optionally further substituted heteroarylcarboxylic acid is thereby converted into the corresponding one by means of a suitable chlorinating agent (eg oxalyl chloride or thionyl chloride) in an aprotic solvent (for example toluene)
Heteroarylcarbonsäurechlorid überführt, falls dieses nicht kommerziell verfügbar ist, und dieses danach mit tert-Butyl-1 -methylhydrazincarboxylat unter Verwendung einer geeigneten Base (z.B. Triethylamin (EtsN)), Di-iso-Propylethylamin) in einem Heteroarylcarboxylic acid chloride, if not commercially available, and thereafter with tert-butyl-1-methylhydrazinecarboxylate using a suitable base (e.g., triethylamine (EtsN)), di-iso -propylethylamine) in one
geeigneten polar-aprotischen Lösemittel (z.B. Tetrahydrofuran (THF) oder suitable polar aprotic solvents (e.g., tetrahydrofuran (THF) or
Dichlormethan (DCM)) zu dem Heteroarylcarbonsaurehydrazid (D) umgesetzt. Das gegebenenfalls weiter substituierte Heteroarylcarbonsaurehydrazid (D) kann auch über eine direkte, durch geeignete Reagenzien (z. B. 1 -Hydroxybenzotriazole (HOBt), N-(3- Dimethylaminopropyl)-N'-ethylcarbodiimid hydrochlorid (EDC) oder 2,4,6-Tripropyl- 1 ,3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxid (T3P) zusammen mit einer geeigneten Base wie z.B. Triethylamin oder Di-iso-Propylethylamin) vermittelte Kupplung einer gegebenenfalls weiter substituierten Heteroarylcarbonsäure mit tert-Butyl-1 - methylhydrazincarboxylat in einem geeigneten polar-aprotischen Lösemittel (z.B. Dichloromethane (DCM)) to give the heteroarylcarboxylic acid hydrazide (D). The optionally further substituted heteroarylcarboxylic acid hydrazide (D) can also be prepared by a direct reaction with suitable reagents (eg 1-hydroxybenzotriazoles (HOBt), N- (3-dimethylaminopropyl) -N'-ethylcarbodiimide hydrochloride (EDC) or 2,4, 6-Tripropyl- 1, 3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide (T3P) together with a suitable base such as triethylamine or di-iso-propylethylamine) mediated coupling of an optionally further substituted heteroarylcarboxylic with tert-butyl-1 - methylhydrazinecarboxylate in a suitable polar aprotic solvent (eg
Dichlormethan, Acetonitril oder Tetrahydrofuran) hergestellt werden. Im nächsten Schritt wird das gegebenenfalls weiter substituierte Heteroarylcarbonsäurehydrazid (D) unter Verwendung eines entsprechend substituierten Arylalkylhalogenids oder Dichloromethane, acetonitrile or tetrahydrofuran). In the next step, the optionally further substituted Heteroarylcarbonsäurehydrazid (D) using an appropriately substituted arylalkyl halide or
Heteroarylalkylhalogenids und einer geeigneten Base (z.B. Natriumhydrid oder Triethylamin (EtsN)) in einem geeigneten Lösemittel (z.B. Tetra hydrofu ran, N,N- Dimethylformamid (DMF) oder Dichlormethan) in ein substituiertes Heteroarylalkylhalogenids and a suitable base (for example, sodium hydride or Triethylamine (EtsN)) in a suitable solvent (eg tetrahydrofuran, N, N-dimethylformamide (DMF) or dichloromethane) into a substituted
Heteroarylcarbonsaurehydrazid (If) überführt (Schema 3). Die tert. Butyloxycarbonyl- Schutzgruppe kann danach durch Behandlung des substituierten Heteroarylcarbonsaurehydrazid (If) transferred (Scheme 3). The tert. Butyloxycarbonyl protective group can then be replaced by treatment of the substituted
Heteroarylcarbonsäurehydrazids (If) mit einer geeigneten Säure (z. B. Heteroarylcarboxylic acid hydrazide (If) with a suitable acid (e.g.
Trifluoressigsäure (TFA)) in einem polar-aprotischen Lösemittel (z. B. Dichlormethan) zum N-mono-substituierten Heteroarylcarbonsaurehydrazid (le) umgesetzt werden. Mit Hilfe eines geeigneten Alkylhalogenids (z. B. Ethyliodid im nachfolgenden Schema 3) unter Verwendung einer geeigneten Base (z. B. Natriumhydrid oder Kaliumcarbonat) in einem geeigneten Lösemittel kann das betreffende N-mono-substituierte  Trifluoroacetic acid (TFA)) in a polar aprotic solvent (e.g., dichloromethane) to the N-mono-substituted heteroarylcarboxylic acid hydrazide (Ie). With the aid of a suitable alkyl halide (e.g., ethyl iodide in Scheme 3 below) using a suitable base (e.g., sodium hydride or potassium carbonate) in a suitable solvent, the subject N-mono-substituted
Heteroarylcarbonsaurehydrazid (le) in ein erfindungsgemäßes gegebenenfalls weiter substituiertes Heteroarylcarbonsäurehydrazid, beispielhaft (Ib) im nachfolgenden Schema 3, mit unsymmetrischen Gruppen am zweiten Hydrazidstickstoff überführt werden. R1, R5 und R6 sowie A1, A2, A3, A4, A5, X1, X2, X3 und Y haben die zuvor definierten Bedeutungen, R3 steht beispielhaft, aber nicht einschränkend, im folgenden Schema 3 für Methyl und W steht beispielhaft, aber nicht einschränkend, für Heteroarylcarbonsaurehydrazid (le) in an inventive optionally further substituted Heteroarylcarbonsäurehydrazid, for example (Ib) in the following Scheme 3, be converted with unsymmetrical groups on the second hydrazide nitrogen. R 1 , R 5 and R 6 and A 1 , A 2 , A 3 , A 4 , A 5 , X 1 , X 2 , X 3 and Y have the meanings defined above, R 3 is exemplary but not limiting, in the following scheme 3 for methyl and W is exemplified, but not limiting, for
Sauerstoff. Oxygen.
Schema 3. Ausgewählte detaillierte Synthesebeispiele für die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) sind im Folgenden aufgeführt. Die angegebenen Scheme 3. Selected detailed synthesis examples of the compounds of the general formula (I) according to the invention are listed below. The specified
Beispielnummern entsprechen den in den nachstehenden Tabellen A1 bis G7 genannten Numerierungen. Die 1H-NMR-, 13C-NMR- und 19F-NMR-spektroskopischen Daten, die für die in den nachfolgenden Abschnitten beschriebenen chemischenExample numbers correspond to the numbers given in Tables A1 to G7 below. The 1 H NMR, 13 C NMR, and 19 F NMR spectroscopic data available for the chemical reactions described in the following sections
Beispiele angegeben sind, (400 MHz bei 1H-NMR und 150 MHz bei 13C-NMR und 375 MHz bei 19F-NMR, Lösungsmittel CDCI3, CD3OD oder de-DMSO, interner Standard: Tetramethylsilan δ = 0.00 ppm), wurden mit einem Gerät der Firma Bruker erhalten, und die bezeichneten Signale haben die nachfolgend aufgeführten Bedeutungen: br = breit(es); s = Singulett, d = Dublett, t = Triplett, dd = Doppeldublett, ddd = Dublett eines Doppeldubletts, m = Multiplett, q = Quartett, quint = Quintett, sext = Sextett, sept = Septett, dq = Doppelquartett, dt = Doppeltriplett. Bei Diastereomerengemischen werden entweder die jeweils signifikanten Signale beider Diastereomere oder das charakteristische Signal des Hauptdiastereomers angegeben. Die verwendeten Abkürzungen für chemische Gruppen haben beispielsweise die nachfolgenden Examples are given (400 MHz at 1 H-NMR and 150 MHz at 13 C-NMR and 375 MHz at 19 F-NMR, solvent CDCl 3 , CD 3 OD or de-DMSO, internal standard: tetramethylsilane δ = 0.00 ppm) , were obtained with a Bruker device, and the designated signals have the meanings given below: br = broad (es); s = singlet, d = doublet, t = triplet, dd = double doublet, ddd = doublet of double doublet, m = multiplet, q = quartet, quint = quintet, sext = sextet, sept = septet, dq = double quartet, dt = double triplet. For diastereomeric mixtures, either the respective significant signals of both diastereomers or the characteristic signal of the main diastereomer are given. The abbreviations used for chemical groups have, for example, the following
Bedeutungen: Me = CH3, Et = CH2CH3, t-Hex = C(CH3)2CH(CH3)2, t-Bu = C(CH3)3, n- Bu = unverzweigtes Butyl, n-Pr = unverzweigtes Propyl, i-Pr = verzweigtes Propyl, c-Pr = Cyclopropyl, c-Hex = Cyclohexyl. Synthesebeispiele: Meanings: Me = CH3, Et = CH2CH3, t-Hex = C (CH 3) 2 CH (CH 3) 2, t-Bu = C (CH 3) 3, n-Bu = unbranched butyl, n-Pr = straight Propyl, i-Pr = branched propyl, c-Pr = cyclopropyl, c-hex = cyclohexyl. Synthesis Examples:
No. A1 -44: N-(4-Brom-2-fluorbenzyl)-5-chlor-N',N',1 -trimethyl-3-(trifluormethyl)-1 H- pyrazol-4-carbohydrazid No. A1 -44: N- (4-bromo-2-fluorobenzyl) -5-chloro-N ', N', 1-trimethyl-3- (trifluoromethyl) -1H-pyrazole-4-carbohydrazide
5-Chlor-1 -methyl-3-(trifluormethyl)-1 H-pyrazol-4-carbonsäure (1000 mg, 4.38 mmol) wurde in einem ausgeheizten Rundkolben unter Argon und bei Raumtemperatur in abs. Dichlormethan (30 ml) gelöst und mit Oxalyichlorid (472 mg, 3.72 mmol) versetzt. Die resultierende Reaktionslösung wurde danach 2 h lang bei Raumtemperatur und 30 Minuten lang unter Rückflußbedingungen gerührt. Nach dem Abkühlen auf Raumtemperatur wurde das Reaktionsgemisch eingeengt und mit wenig abs. Toluol co-evaporiert. Durch gründliches Entfernen von Lösemittelresten wurde 5-Chlor-1 - methyl-3-(trifluormethyl)-1 H-pyrazol-4-carbonylchlorid (1080 mg, 4.37 mmol) erhalten, das danach ohne weitere Reinigung erneut in abs. Dichlormethan (10 ml) gelöst und tropfenweise zu einer auf 0 °C eingekühlten Lösung von N,N-Dimethylhydrazin (263 mg, 4.37 mmol) sowie Triethylamin (0.73 ml, 5.25 mmol) in Dichlormethan (10 ml) unter Argon gegeben wurde. Das resultierende Reaktionsgemisch wurde 30 Minuten lang bei Raumtemperatur nachgerührt und danach mit Wasser und Dichlormethan versetzt. Die wäßrige Phase wurde mehrfach intensiv mit Dichlormethan extrahiert, und die vereinigten organischen Phasen wurden danach über Magnesiumsulfat getrocknet, filtriert und eingeengt. Durch abschließende säulenchromatographische Reinigung des resultierenden Rohproduktes konnte 5-Chlor-N',N',1 -trimethyl-3- (trifluormethyl)-l H-pyrazol-4-carbohydrazid in Form eines farblosen Feststoffs isoliert werden (1 160 mg, 98% der Theorie). 1H-NMR (400 MHz, CDCIs δ, ppm) 6.68-6.50 (br. s, 1 H, NH), 3.91 (s, 3H), 2.70 (s, 6H). 5-Chlor-N',N',1 -trimethyl-3-(trifluormethyl)-1 H- pyrazol-4-carbohydrazid (200 mg, 0.74 mmol) wurde in abs. Tetra hydrofu ran (5 ml) unter Argon gelöst und bei Raumtemperatur mit Natriumhydrid (33 mg, 0.81 mmol, 60%ige Reinheit) versetzt. Nach 30 Minuten Rühren bei Raumtemperatur erfolgte die Zugabe von 2-Fluor-4-Brombenzylchlorid (165 mg, 0.74 mmol), und das resultierende Reaktionsgemisch wurde 3 Stunden lang unter Rückflußbedingungen gerührt. Nach dem Abkühlen auf Raumtemperatur wurden ges. Natriumhydrogencarbonat-Lösung, Wasser und Dichlormethan zugegeben. Die wäßrige Phase wurde mehrfach intensiv mit Dichlormethan extrahiert, und die vereinigten organischen Phasen wurden danach über Magnesiumsulfat getrocknet, filtriert und eingeengt. Durch abschließende säulenchromatographische Reinigung des resultierenden Rohproduktes konnte N-(4- Brom-2-fluorbenzyl)-5-chlor-N',N',1 -trimethyl-3-(trifluormethyl)-1 H-pyrazol-4- carbohydrazid in Form eines farblosen Feststoffs isoliert werden (169 mg, 50% der Theorie). 1H-NMR (400 MHz, CDCIs δ, ppm) 7.60-7.55 (m, 1 H), 7.37-7.32 (m, 2H), 5.07 (s, 2H), 3.85 (s, 3H), 3.36 (s, 6H). 5-Chloro-1-methyl-3- (trifluoromethyl) -1H-pyrazole-4-carboxylic acid (1000 mg, 4.38 mmol) was dissolved in abs. Dissolved dichloromethane (30 ml) and treated with Oxalyichlorid (472 mg, 3.72 mmol). The resulting reaction solution was then left at room temperature for 30 minutes and 30 minutes Stirred under reflux conditions for minutes. After cooling to room temperature, the reaction mixture was concentrated and extracted with a little abs. Toluene co-evaporated. Thorough removal of solvent residues gave 5-chloro-1-methyl-3- (trifluoromethyl) -1H-pyrazole-4-carbonyl chloride (1080 mg, 4.37 mmol), which was then redissolved in abs. Dichloromethane (10ml) and added dropwise to a solution of N, N-dimethylhydrazine (263mg, 4.37mmol) cooled to 0 ° C and triethylamine (0.73ml, 5.25mmol) in dichloromethane (10ml) under argon. The resulting reaction mixture was stirred for 30 minutes at room temperature and then treated with water and dichloromethane. The aqueous phase was repeatedly extracted intensively with dichloromethane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography of the resulting crude product isolated 5-chloro-N ', N', 1-trimethyl-3- (trifluoromethyl) -1H-pyrazole-4-carbohydrazide in the form of a colorless solid (1,160 mg, 98%). the theory). 1 H-NMR (400 MHz, CDCIs δ, ppm) 6.68-6.50 (br. S, 1 H, NH), 3.91 (s, 3H), 2.70 (s, 6H). 5-Chloro-N ', N', 1-trimethyl-3- (trifluoromethyl) -1H-pyrazole-4-carbohydrazide (200 mg, 0.74 mmol) was dissolved in abs. Tetra hydrofu ran (5 ml) under argon and at room temperature with sodium hydride (33 mg, 0.81 mmol, 60% pure) was added. After stirring at room temperature for 30 minutes, 2-fluoro-4-bromobenzyl chloride (165 mg, 0.74 mmol) was added, and the resulting reaction mixture was stirred at reflux for 3 hours. After cooling to room temperature, sat. Sodium bicarbonate solution, water and dichloromethane added. The aqueous phase was repeatedly extracted intensively with dichloromethane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography of the resulting crude product gave N- (4-bromo-2-fluorobenzyl) -5-chloro-N ', N', 1-trimethyl-3- (trifluoromethyl) -1H-pyrazole-4-carbohydrazide in the form of a colorless solid (169 mg, 50% of theory). 1 H-NMR (400 MHz, CDCl3 δ, ppm) 7.60-7.55 (m, 1H), 7.37-7.32 (m, 2H), 5.07 (s, 2H), 3.85 (s, 3H), 3.36 (s, 6H).
No. A2-35: N-[(3,5-Dichlorpyridin-2-yl)methyl]-5-fluor-N',N',1 -trimethyl-3-(trifluormethyl)- 1 H-pyrazol-4-carbohydrazid No. A2-35: N - [(3,5-dichloropyridin-2-yl) methyl] -5-fluoro-N ', N', 1-trimethyl-3- (trifluoromethyl) -1 H -pyrazole-4-carbohydrazide
5-Fluor-1 -methyl-3-(trifluornnethyl)-1 H-pyrazol-4-carbonsäure (1 .0 equiv) wurde in einem ausgeheizten Rundkolben unter Argon und bei Raumtemperatur in abs. 5-Fluoro-1-methyl-3- (trifluoromethyl) -1H-pyrazole-4-carboxylic acid (1 .0 equiv) was dissolved in a heated round bottom flask under argon and at room temperature in abs.
Dichlormethan (10 ml/mmol) gelöst und mit Oxalylchlorid (0.75 equiv) versetzt. Die resultierende Reaktionslösung wurde danach 2 h lang bei Raumtemperatur und 30 Minuten lang unter Rückflußbedingungen gerührt. Nach dem Abkühlen auf Dissolved dichloromethane (10 ml / mmol) and treated with oxalyl chloride (0.75 equiv). The resulting reaction solution was then stirred for 2 hours at room temperature and for 30 minutes under reflux conditions. After cooling to
Raumtemperatur wurde das Reaktionsgemisch eingeengt und mit wenig abs. Toluol co-evaporiert. Durch gründliches Entfernen von Lösemittel resten wurde 5-Fluor-1 - methyl-3-(trifluormethyl)-1 H-pyrazol-4-carbonylchlorid erhalten, das danach ohne weitere Reinigung erneut in abs. Dichlormethan (10 ml) gelöst und tropfenweise zu einer auf 0 °C eingekühlten Lösung von N,N-Dimethylhydrazin (1 equiv) sowie Room temperature, the reaction mixture was concentrated and extracted with a little abs. Toluene co-evaporated. Thorough removal of solvent residues gave 5-fluoro-1-methyl-3- (trifluoromethyl) -1H-pyrazole-4-carbonyl chloride, which was then redissolved in abs. Dichloromethane (10 ml) and added dropwise to a cooled to 0 ° C solution of N, N-dimethylhydrazine (1 equiv.) And
Triethylamin (1 .3 equiv) in Dichlormethan (2 ml/mmol) unter Argon gegeben wurde. Das resultierende Reaktionsgemisch wurde 30 Minuten lang bei Raumtemperatur nachgerührt und danach mit Wasser und Dichlormethan versetzt. Die wäßrige Phase wurde mehrfach intensiv mit Dichlormethan extrahiert, und die vereinigten organischen Phasen wurden danach über Magnesiumsulfat getrocknet, filtriert und eingeengt. Durch abschließende säulenchromatographische Reinigung des resultierenden Rohproduktes konnte 5-Fluor-N',N',1 -trimethyl-3-(trifluormethyl)-1 H-pyrazol-4- carbohydrazid in Form eines farblosen Feststoffs isoliert werden. 5-Fluor-N',N',1 - trimethyl-3-(trifluormethyl)-1 H-pyrazol-4-carbohydrazid (129 mg, 0.51 mmol) wurde in abs. Tetrahydrofuran (5 ml) unter Argon gelöst und bei Raumtemperatur mit Triethylamine (1: 3 equiv) in dichloromethane (2 ml / mmol) was added under argon. The resulting reaction mixture was stirred for 30 minutes at room temperature and then treated with water and dichloromethane. The aqueous phase was repeatedly extracted intensively with dichloromethane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography of the resulting crude product afforded the isolation of 5-fluoro-N ', N', 1-trimethyl-3- (trifluoromethyl) -1H-pyrazole-4-carbohydrazide as a colorless solid. 5-Fluoro-N ', N', 1-trimethyl-3- (trifluoromethyl) -1H-pyrazole-4-carbohydrazide (129 mg, 0.51 mmol) was dissolved in abs. Tetrahydrofuran (5 ml) was dissolved under argon and at room temperature with
Natriumhydrid (24 mg, 0.61 mmol, 60%ige Reinheit) versetzt. Nach 30 Minuten Rühren bei Raumtemperatur erfolgte die Zugabe von 2-Chlormethyl-3,5-dichlorpyridin (99 mg, 0.51 mmol), und das resultierende Reaktionsgemisch wurde zweieinhalb Stunden lang unter Rückflußbedingungen gerührt. Nach dem Abkühlen auf Raumtemperatur wurden ges. Natriumhydrogencarbonat-Lösung, Wasser und Dichlormethan zugegeben. Die wäßrige Phase wurde mehrfach intensiv mit Dichlormethan extrahiert, und die vereinigten organischen Phasen wurden danach über Magnesiumsulfat getrocknet, filtriert und eingeengt. Durch abschließende säulenchromatographische Reinigung des resultierenden Rohproduktes konnte N-[(3,5-Dichlorpyridin-2-yl)methyl]-5-fluor-N',N',1 - trimethyl-3-(trifluormethyl)-1 H-pyrazol-4-carbohydrazid in Form eines farblosen Sodium hydride (24 mg, 0.61 mmol, 60% purity) was added. After stirring at room temperature for 30 minutes, 2-chloromethyl-3,5-dichloropyridine (99 mg, 0.51 mmol) was added, and the resulting reaction mixture was stirred under reflux conditions for two and a half hours. After cooling to room temperature, sat. Sodium bicarbonate solution, water and dichloromethane added. The aqueous phase was repeatedly extracted intensively with dichloromethane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography of the resulting crude product afforded N - [(3,5-dichloropyridin-2-yl) methyl] -5-fluoro-N ', N', 1-trimethyl-3- (trifluoromethyl) -1H-pyrazole 4-carbohydrazide in the form of a colorless
Feststoffs isoliert werden (132 mg, 63% der Theorie). 1H-NMR (400 MHz, CDCIs δ, ppm) 8.55 (m, 1 H), 7.84 (m, 1 H), 5.27 (s, 2H), 3.76 (s, 3H), 3.51 (s, 6H). Be isolated solid (132 mg, 63% of theory). 1 H-NMR (400 MHz, CDCl3 δ, ppm) 8.55 (m, 1H), 7.84 (m, 1H), 5.27 (s, 2H), 3.76 (s, 3H), 3.51 (s, 6H).
No. A4-4: N-(2,3-Dichlorbenzyl)-N',N',1 -trimethyl-3-(trifluormethyl)-1 H-pyrazol-4- carbohydrazid No. A4-4: N- (2,3-dichlorobenzyl) -N ', N', 1-trimethyl-3- (trifluoromethyl) -1H-pyrazole-4-carbohydrazide
1 -Methyl-3-(trifluormethyl)-1 H-pyrazol-4-carbonsäure (700 mg, 3.61 mmol) wurde in abs. Dichlormethan (15 ml) gelöst und mit Triethylamin (1 .51 ml, 10.82 mmol) versetzt. Nach 5 Minuten Rühren bei Raumtemperatur erfolgte die Zugabe von N,N- Dimethylhydrazin (0.33 ml, 4.33 mmol) und von 2,4,6-Tripropyl-1 ,3,5,2,4,6- trioxatriphosphorinan-2,4,6-trioxid (3.22 ml, 5.41 mmol, 50% Lösung in 1-Methyl-3- (trifluoromethyl) -1H-pyrazole-4-carboxylic acid (700 mg, 3.61 mmol) was dissolved in abs. Dissolve dichloromethane (15 mL) and add triethylamine (1.51 mL, 10.82 mmol). After stirring at room temperature for 5 minutes, N, N-dimethylhydrazine (0.33 ml, 4.33 mmol) and 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphorinan-2,4 were added, 6-trioxide (3.22 ml, 5.41 mmol, 50% solution in
Tetrahydrofuran). Das resultierende Reaktionsgemisch wurde 30 Minuten lang bei Raumtemperatur nachgerührt und danach mit Wasser, ges. Tetrahydrofuran). The resulting reaction mixture was stirred for 30 minutes at room temperature and then washed with water, sat.
Natriumhydrogencarbonatlösung und Dichlormethan versetzt. Die wäßrige Phase wurde mehrfach intensiv mit Dichlormethan extrahiert, und die vereinigten organischen Phasen wurden danach über Magnesiumsulfat getrocknet, filtriert und eingeengt. Sodium bicarbonate solution and dichloromethane. The aqueous phase was repeatedly extracted intensively with dichloromethane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated.
Durch abschließende säulenchromatographische Reinigung des resultierenden By final column chromatographic purification of the resulting
Rohproduktes konnte N',N',1 -Trimethyl-3-(trifluormethyl)-1 H-pyrazol-4-carbohydrazid in Form eines farblosen Feststoffs isoliert werden (430 mg, 50% der Theorie). 1H-NMR (400 MHz, CDCIs δ, ppm) 7.96 (m, 1 H), 7.27 (m, 1 H), 6.69 (br. s, 1 H, NH), 3.96 (s, 3H), 2.68 (s, 6H). N',N',1 -Trimethyl-3-(trifluormethyl)-1 H-pyrazol-4-carbohydrazid (140 mg, 0.59 mmol) wurde in abs. Tetrahydrofuran (10 ml) unter Argon gelöst und bei Crude product could be isolated N ', N', 1-trimethyl-3- (trifluoromethyl) -1H-pyrazole-4-carbohydrazide in the form of a colorless solid (430 mg, 50% of theory). 1 H-NMR (400 MHz, CDCl3 δ, ppm) 7.96 (m, 1H), 7.27 (m, 1H), 6.69 (br.s, 1H, NH), 3.96 (s, 3H), 2.68 ( s, 6H). N ', N', 1-trimethyl-3- (trifluoromethyl) -1H-pyrazole-4-carbohydrazide (140 mg, 0.59 mmol) was dissolved in abs. Dissolved tetrahydrofuran (10 ml) under argon and at
Raumtemperatur mit Natriumhydrid (28 mg, 0.71 mmol, 60%ige Reinheit) versetzt. Nach 30 Minuten Rühren bei Raumtemperatur erfolgte die Zugabe von 2,3- Dichlorbenzylchlorid (1 16 mg, 0.59 mmol), und das resultierende Reaktionsgemisch wurde 3 Stunden lang unter Rückflußbedingungen gerührt. Nach dem Abkühlen auf Raumtemperatur wurden ges. Natriumhydrogencarbonat-Lösung, Wasser und Room temperature with sodium hydride (28 mg, 0.71 mmol, 60% purity) was added. After stirring for 30 minutes at room temperature, the addition of 2,3-dichlorobenzyl chloride (1 16 mg, 0.59 mmol), and the resulting reaction mixture was stirred under reflux conditions for 3 hours. After cooling to room temperature, sat. Sodium bicarbonate solution, water and
Dichlormethan zugegeben. Die wäßrige Phase wurde mehrfach intensiv mit Dichloromethane added. The aqueous phase was repeatedly intensively with
Dichlormethan extrahiert, und die vereinigten organischen Phasen wurden danach über Magnesiumsulfat getrocknet, filtriert und eingeengt. Durch abschließende saulenchromatographische Reinigung des resultierenden Rohproduktes konnte N-(2,3- Dichlorbenzyl)-N',N',1 -trimethyl-3-(trifluormethyl)-1 H-pyrazol-4-carbohydrazid in Form eines farblosen zähen Öls isoliert werden (127 mg, 54% der Theorie). 1H-NMR (400 MHz, CDCIs δ, ppm) 7.69 (s, 1 H), 7.62 (m, 1 H), 7.55 (m, 1 H), 7.23 (m, 1 H), 5.30 (s, 2H), 3.89 (s, 3H), 3.39 (s, 6H). Dichloromethane extracted, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography of the resulting crude product gave N- (2,3-dichlorobenzyl) -N ', N', 1-trimethyl-3- (trifluoromethyl) -1H-pyrazole-4-carbohydrazide as a colorless, viscous oil (127 mg, 54% of theory). 1 H-NMR (400 MHz, CDCls δ, ppm) 7.69 (s, 1H), 7.62 (m, 1H), 7.55 (m, 1H), 7.23 (m, 1H), 5.30 (s, 2H ), 3.89 (s, 3H), 3.39 (s, 6H).
No. A6-21 : 5-Chlor-3-(difluormethyl)-N',N',1 -trimethyl-N-(pyridin-2-ylmethyl)-1 H- pyrazol-4-carbohydrazid No. A6-21: 5-chloro-3- (difluoromethyl) -N ', N', 1-trimethyl-N- (pyridin-2-ylmethyl) -1H-pyrazole-4-carbohydrazide
5-Chlor-3-(difluormethyl)-1 -methyl-1 H-pyrazol-4-carbonsäure (700 mg, 2.38 mmol) wurde in einem ausgeheizten Rundkolben unter Argon und bei Raumtemperatur in abs. Dichlormethan (20 ml) gelöst und mit Oxalylchlorid (257 mg, 2.02 mmol) sowie katalytischen Mengen Ν,Ν-Dimethylformamid versetzt. Die resultierende 5-Chloro-3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxylic acid (700 mg, 2.38 mmol) was dissolved in abs. Dissolved dichloromethane (20 ml) and treated with oxalyl chloride (257 mg, 2.02 mmol) and catalytic amounts of Ν, Ν-dimethylformamide. The resulting
Reaktionslösung wurde danach 3 h lang unter Rückflußbedingungen gerührt. Nach dem Abkühlen auf Raumtemperatur wurde das Reaktionsgemisch eingeengt und mit wenig abs. Toluol co-evaporiert. Durch gründliches Entfernen von Lösemittel resten wurde 5-Chlor-3-(difluormethyl)-1 -methyl-1 H-pyrazol-4-carbonylchlorid (743 mg, 2.38 mmol) erhalten, das danach ohne weitere Reinigung erneut in abs. Dichlormethan (10 ml) gelöst und tropfenweise zu einer auf 0 °C eingekühlten Lösung von N,N- Dimethylhydrazin (0.18 ml, 2.38 mmol) sowie Triethylamin (0.40 ml, 2.85 mmol) in Dichlormethan (10 ml) unter Argon gegeben wurde. Das resultierende  Reaction solution was then stirred for 3 hours under reflux conditions. After cooling to room temperature, the reaction mixture was concentrated and extracted with a little abs. Toluene co-evaporated. Thorough removal of solvent residues gave 5-chloro-3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carbonyl chloride (743 mg, 2.38 mmol), which was then redissolved in abs. Dichloromethane (10ml) and added dropwise to a solution of N, N-dimethylhydrazine (0.18ml, 2.38mmol) cooled to 0 ° C and triethylamine (0.40ml, 2.85mmol) in dichloromethane (10ml) under argon. The resulting
Reaktionsgemisch wurde 30 Minuten lang bei Raumtemperatur nachgerührt und danach mit Wasser und Dichlormethan versetzt. Die wäßrige Phase wurde mehrfach intensiv mit Dichlormethan extrahiert, und die vereinigten organischen Phasen wurden danach über Magnesiumsulfat getrocknet, filtriert und eingeengt. Durch abschließende säulenchromatographische Reinigung des resultierenden Rohproduktes konnte 5- Chlor-3-(difluormethyl)-N',N',1 -trimethyl-1 H-pyrazol-4-carbohydrazid in Form eines farblosen Feststoffs isoliert werden (541 mg, 90% der Theorie). 5-Chlor-3-The reaction mixture was stirred for 30 minutes at room temperature and then treated with water and dichloromethane. The aqueous phase was multiply extracted intensively with dichloromethane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography of the resulting crude product afforded the isolation of 5-chloro-3- (difluoromethyl) -N ', N', 1-trimethyl-1H-pyrazole-4-carbohydrazide as a colorless solid (541 mg, 90% of Theory). 5-chloro-3-
(difluormethyl)-N',N',1 -trimethyl-1 H-pyrazol-4-carbohydrazid (212 mg, 0.84 mmol) wurde in abs. Tetrahydrofuran (5 ml) unter Argon gelöst und bei Raumtemperatur mit Natriumhydrid (37 mg, 0.92 mmol, 60%ige Reinheit) versetzt. Nach 30 Minuten Rühren bei Raumtemperatur erfolgte die Zugabe von Picolylchlorid (107 mg, 0.84 mmol), und das resultierende Reaktionsgemisch wurde 2 Stunden lang unter (Difluoromethyl) -N ', N', 1-trimethyl-1H-pyrazole-4-carbohydrazide (212 mg, 0.84 mmol) was dissolved in abs. Dissolved tetrahydrofuran (5 ml) under argon and at room temperature with sodium hydride (37 mg, 0.92 mmol, 60% purity) was added. After stirring at room temperature for 30 minutes, the addition of picolyl chloride (107 mg, 0.84 mmol) was carried out, and the resulting reaction mixture was allowed to stand for 2 hours
Rückflußbedingungen gerührt. Nach dem Abkühlen auf Raumtemperatur wurden ges. Natriumhydrogencarbonat-Lösung, Wasser und Dichlormethan zugegeben. Die wäßrige Phase wurde mehrfach intensiv mit Dichlormethan extrahiert, und die vereinigten organischen Phasen wurden danach über Magnesiumsulfat getrocknet, filtriert und eingeengt. Durch abschließende säulenchromatographische Reinigung des resultierenden Rohproduktes konnte 5-Chlor-3-(difluormethyl)-N',N',1 -trimethyl-N- (pyridin-2-ylmethyl)-1 H-pyrazol-4-carbohydrazid in Form eines farblosen Feststoffs isoliert werden (196 mg, 68% der Theorie). 1H-NMR (400 MHz, CDCIs δ, ppm) 8.64 (m, 1 H), 7.73 (m, 1 H), 7.63 (m, 1 H), 7.36 (m, 1 H), 7.15-6.88 (br. t, 1 H, CHF2), 5.1 1 (s, 2H), 3.86 (s, 3H), 3.48 (s, 6H). Reflux conditions stirred. After cooling to room temperature, sat. Sodium bicarbonate solution, water and dichloromethane added. The aqueous phase was repeatedly extracted intensively with dichloromethane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography of the resulting crude product gave 5-chloro-3- (difluoromethyl) -N ', N', 1-trimethyl-N- (pyridin-2-ylmethyl) -1H-pyrazole-4-carbohydrazide as a colorless Be isolated solid (196 mg, 68% of theory). 1 H-NMR (400 MHz, CDCls δ, ppm) 8.64 (m, 1H), 7.73 (m, 1H), 7.63 (m, 1H), 7.36 (m, 1H), 7.15-6.88 (br t, 1H, CHF 2 ), 5.1 1 (s, 2H), 3.86 (s, 3H), 3.48 (s, 6H).
No. A7-4: N-(2,3-Dichlorbenzyl)-3-(difluormethyl)-1 -ethyl-5-fluor-N',N'-dimethyl-1 H- pyrazol-4-carbohydrazid No. A7-4: N- (2,3-dichlorobenzyl) -3- (difluoromethyl) -1-ethyl-5-fluoro-N ', N'-dimethyl-1H-pyrazole-4-carbohydrazide
5-Fluor-3-(difluormethyl)-1 -ethyl-1 H-pyrazol-4-carbonsäure (300 mg, 1 .44 mmol) wurde in abs. Dichlormethan (20 ml) gelöst und mit Triethylamin (0.60 ml, 4.32 mmol) versetzt. Nach 5 Minuten Rühren bei Raumtemperatur erfolgte die Zugabe von N,N- Dimethylhydrazin (0.13 ml, 1 .73 mmol) und von 2,4,6-Tripropyl-1 ,3,5,2,4,6- trioxatriphosphorinan-2,4,6-trioxid (1 .29 ml, 2.16 mmol, 50% Lösung in Tetrahydrofuran). Das resultierende Reaktionsgemisch wurde 30 Minuten lang bei Raumtemperatur nachgerührt und danach mit Wasser, ges. 5-Fluoro-3- (difluoromethyl) -1-ethyl-1H-pyrazole-4-carboxylic acid (300 mg, 1 .44 mmol) was dissolved in abs. Dissolved dichloromethane (20 ml) and treated with triethylamine (0.60 ml, 4.32 mmol). After stirring at room temperature for 5 minutes, N, N-dimethylhydrazine (0.13 ml, 1.73 mmol) and 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphorinan-2 were added, 4,6-trioxide (1 .29 ml, 2.16 mmol, 50% solution in Tetrahydrofuran). The resulting reaction mixture was stirred for 30 minutes at room temperature and then washed with water, sat.
Natriumhydrogencarbonatlösung und Dichlormethan versetzt. Die wäßrige Phase wurde mehrfach intensiv mit Dichlormethan extrahiert, und die vereinigten organischen Phasen wurden danach über Magnesiumsulfat getrocknet, filtriert und eingeengt. Sodium bicarbonate solution and dichloromethane. The aqueous phase was repeatedly extracted intensively with dichloromethane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated.
Durch abschließende saulenchromatographische Reinigung des resultierenden By final column chromatographic purification of the resulting
Rohproduktes konnte 5-Fluor-3-(difluormethyl)-N',N'-dimethyl-1 -ethyl-1 H-pyrazol-4- carbohydrazid in Form eines farblosen Feststoffs isoliert werden (309 mg, 86% der Theorie). 1H-NMR (400 MHz, CDCIs δ, ppm) 7.06-6.79 (br. t, 1 H, CHF2) 6.78 (br. s, 1 H, NH), 4.15-4.10 (q, 2H), 2.69 (s, 6H), 1 .47 (t, 3H). 5-Fluor-3-(difluormethyl)-N',N'- dimethyl-1 -ethyl-1 H-pyrazol-4-carbohydrazid (100 mg, 0.40 mmol) wurde in abs. Crude product, 5-fluoro-3- (difluoromethyl) -N ', N'-dimethyl-1-ethyl-1 H-pyrazole-4-carbohydrazide could be isolated as a colorless solid (309 mg, 86% of theory). 1 H-NMR (400 MHz, CDCIs δ, ppm) 7.06-6.79 (br. T, 1H, CHF 2), 6.78 (br. S, 1 H, NH), 4:15 to 4:10 (q, 2H), 2.69 ( s, 6H), 1 .47 (t, 3H). 5-Fluoro-3- (difluoromethyl) -N ', N'-dimethyl-1-ethyl-1H-pyrazole-4-carbohydrazide (100 mg, 0.40 mmol) was dissolved in abs.
Tetrahydrofuran (5 ml) unter Argon gelöst und bei Raumtemperatur mit Natriumhydrid (19 mg, 0.48 mmol, 60%ige Reinheit) versetzt. Nach 30 Minuten Rühren bei Dissolved tetrahydrofuran (5 ml) under argon and at room temperature with sodium hydride (19 mg, 0:48 mmol, 60% purity) was added. After stirring for 30 minutes
Raumtemperatur erfolgte die Zugabe von 2,3-Dichlorbenzylchlorid (78 mg, 0.40 mmol), und das resultierende Reaktionsgemisch wurde ca. 3 Stunden lang unter Room temperature, the addition of 2,3-dichlorobenzyl chloride (78 mg, 0.40 mmol), and the resulting reaction mixture was about 3 hours under
Rückflußbedingungen gerührt. Nach dem Abkühlen auf Raumtemperatur wurden ges. Natriumhydrogencarbonat-Lösung, Wasser und Dichlormethan zugegeben. Die wäßrige Phase wurde mehrfach intensiv mit Dichlormethan extrahiert, und die vereinigten organischen Phasen wurden danach über Magnesiumsulfat getrocknet, filtriert und eingeengt. Durch abschließende säulenchromatographische Reinigung des resultierenden Rohproduktes konnte N-(2,3-Dichlorbenzyl)-3-(difluormethyl)-1 -ethyl-5- fluor-N',N'-dimethyl-1 H-pyrazol-4-carbohydrazid in Form eines zähen Öls isoliert werden (72 mg, 44% der Theorie). 1H-NMR (400 MHz, CDCIs δ, ppm) 7.63 (m, 1 H), 7.57 (m, 1 H), 7.28 (m, 1 H), 7.27-7.00 (br. t, 1 H, CHF2), 5.26 (s, 2H), 4.14-4.09 (q, 2H), 3.41 (s, 6H), 1 .45 (t, 3H). Reflux conditions stirred. After cooling to room temperature, sat. Sodium bicarbonate solution, water and dichloromethane added. The aqueous phase was repeatedly extracted intensively with dichloromethane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography of the resulting crude product gave N- (2,3-dichlorobenzyl) -3- (difluoromethyl) -1-ethyl-5-fluoro-N ', N'-dimethyl-1H-pyrazole-4-carbohydrazide in the form of of a viscous oil (72 mg, 44% of theory). 1 H-NMR (400 MHz, CDCl 2 δ, ppm) 7.63 (m, 1H), 7.57 (m, 1H), 7.28 (m, 1H), 7.27-7.00 (br.t, 1H, CHF 2 ), 5.26 (s, 2H), 4.14-4.09 (q, 2H), 3.41 (s, 6H), 1.45 (t, 3H).
No. A18-21 : 3-(Difluormethyl)-1 -methyl-5-chlor-N-(pyridin-2-ylmethyl)-N-(pyrrolidin-1 - yl)-1 H-pyrazol-4-carboxamid No. A18-21: 3- (Difluoromethyl) -1-methyl-5-chloro-N- (pyridin-2-ylmethyl) -N- (pyrrolidin-1-yl) -1H-pyrazole-4-carboxamide
5-Clor-3-(difluormethyl)-1 -methyl-1 H-pyrazol-4-carbonsäure (400 mg, 1 .90 mmol) wurde in abs. Dichlormethan (20 ml) gelöst und mit Triethylamin (0.79 ml, 5.69 mmol) versetzt. Nach 5 Minuten Rühren bei Raumtemperatur erfolgte die Zugabe von 5-Clor-3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxylic acid (400 mg, 1.90 mmol) was dissolved in abs. Dissolved dichloromethane (20 ml) and treated with triethylamine (0.79 ml, 5.69 mmol). After stirring for 5 minutes at room temperature, the addition of
Pyrrolidin-1 -amin (197 mg, 2.28 mmol) und von 2,4,6-Tripropyl-1 ,3,5,2,4,6- trioxatriphosphorinan-2,4,6-trioxid (1 .69 ml, 2.85 mmol, 50% Lösung in Pyrrolidine-1-amine (197 mg, 2.28 mmol) and 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide (1 .69 ml, 2.85 mmol) mmol, 50% solution in
Tetrahydrofuran). Das resultierende Reaktionsgemisch wurde 30 Minuten lang bei Raumtemperatur nachgerührt und danach mit Wasser, ges.  Tetrahydrofuran). The resulting reaction mixture was stirred for 30 minutes at room temperature and then washed with water, sat.
Natriumhydrogencarbonatlösung und Dichlormethan versetzt. Die wäßrige Phase wurde mehrfach intensiv mit Dichlormethan extrahiert, und die vereinigten organischen Phasen wurden danach über Magnesiumsulfat getrocknet, filtriert und eingeengt. Sodium bicarbonate solution and dichloromethane. The aqueous phase was repeatedly extracted intensively with dichloromethane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated.
Durch abschließende saulenchromatographische Reinigung des resultierenden Rohproduktes konnte 5-Chlor 3-(difluormethyl)-1 -methyl-N-(pyrrolidin-1 -yl)-1 H-pyrazol- 4-carboxamid in Form eines farblosen Feststoffs isoliert werden (340 mg, 64% der Theorie). 1H-NMR (400 MHz, CDCIs δ, ppm) 7.13-6.86 (br. t, 1 H, CHF2), 6.31 (br. s, 1 H, NH), 3.91 (s, 3H), 3.02 (m, 4H), 1 .92 (m, 4H). 5-Chlor 3-(difluormethyl)-1 -methyl- N-(pyrrolidin-1 -yl)-1 H-pyrazol-4-carboxamid (130 mg, 0.47 mmol) wurde in abs. Final purification by column chromatography of the resulting crude product gave 5-chloro-3- (difluoromethyl) -1-methyl-N- (pyrrolidin-1-yl) -1H-pyrazole-4-carboxamide as a colorless solid (340 mg; 64% of theory). 1 H-NMR (400 MHz, CDCIs δ, ppm) 7.13-6.86 (br t, 1 H, CHF 2 ), 6.31 (br s, 1 H, NH), 3.91 (s, 3H), 3.02 (m , 4H), 1 .92 (m, 4H). 5-Chloro-3- (difluoromethyl) -1-methyl-N- (pyrrolidin-1-yl) -1H-pyrazole-4-carboxamide (130 mg, 0.47 mmol) was dissolved in abs.
Tetrahydrofuran (5 ml) unter Argon gelöst und bei Raumtemperatur mit Natriumhydrid (41 mg, 1 .03 mmol, 60%ige Reinheit) versetzt. Nach 30 Minuten Rühren bei Tetrahydrofuran (5 ml) was dissolved under argon and treated at room temperature with sodium hydride (41 mg, 1 .03 mmol, 60% pure). After stirring for 30 minutes
Raumtemperatur erfolgte die Zugabe von Picolyichlorid (HCI-Salz, 77 mg, 0.47 mmol), und das resultierende Reaktionsgemisch wurde ca. zweieinhalb Stunden lang unter Rückflußbedingungen gerührt. Nach dem Abkühlen auf Raumtemperatur wurden ges. Natriumhydrogencarbonat-Lösung, Wasser und Dichlormethan zugegeben. Die wäßrige Phase wurde mehrfach intensiv mit Dichlormethan extrahiert, und die vereinigten organischen Phasen wurden danach über Magnesiumsulfat getrocknet, filtriert und eingeengt. Durch abschließende säulenchromatographische Reinigung des resultierenden Rohproduktes konnte 3-(Difluormethyl)-1 -methyl-5-chlor-N-(pyridin-2- ylmethyl)-N-(pyrrolidin-1 -yl)-1 H-pyrazol-4-carboxamid in Form eines farblosen Room temperature, the addition of picrolichloride (HCl salt, 77 mg, 0.47 mmol) and the resulting reaction mixture was stirred for approximately two and a half hours under reflux conditions. After cooling to room temperature, sat. Sodium bicarbonate solution, water and dichloromethane added. The aqueous phase was repeatedly extracted intensively with dichloromethane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography of the resulting crude product afforded 3- (difluoromethyl) -1-methyl-5-chloro-N- (pyridin-2-ylmethyl) -N- (pyrrolidin-1-yl) -1H-pyrazole-4-carboxamide in the form of a colorless
Feststoffs isoliert werden (66 mg, 28% der Theorie). 1H-NMR (400 MHz, CDCIs δ, ppm) 8.60 (m, 1 H), 7.68 (m, 1 H), 7.55 (m, 1 H), 7.30 (m, 1 H), 7.1 1 -6.83 (br. t, 1 H, CHF2), 5.22 (s, 2H), 4.21 -4.13 (m, 2H), 3.85 (s, 3H), 3.65-3.56 (m, 2H), 2.32-2.24 (m, 2H), 2.12-2.03 (m, 2H). No. A20-21 : 3-(Difluormethyl)-1 -methyl-N-(pyndin-2-ylmethyl)-N-(pyrrolidin-1 -yl)-1 H- pyrazol-4-carboxamid Be isolated solid (66 mg, 28% of theory). 1 H-NMR (400 MHz, CDCl3 δ, ppm) 8.60 (m, 1H), 7.68 (m, 1H), 7.55 (m, 1H), 7.30 (m, 1H), 7.1 1 -6.83 ( t, 1H, CHF 2 ), 5.22 (s, 2H), 4.21 -4.13 (m, 2H), 3.85 (s, 3H), 3.65-3.56 (m, 2H), 2.32-2.24 (m, 2H ), 2.12-2.03 (m, 2H). No. A20-21: 3- (Difluoromethyl) -1-methyl-N- (pyndin-2-ylmethyl) -N- (pyrrolidin-1-yl) -1H-pyrazole-4-carboxamide
3-(Difluormethyl)-1 -nnethyl-1 H-pyrazol-4-carbonylchlorid (458 mg, 2.35 mmol) wurde in abs. Dichlormethan (5 ml) gelöst und tropfenweise zu einer auf 0 °C eingekühlten Lösung von Pyrrolidin-1 -amin (203 mg, 2.35 mmol) sowie Triethylamin (0.39 ml, 2.82 mmol) in Dichlormethan (10 ml) unter Argon gegeben wurde. Das resultierende 3- (Difluoromethyl) -1-methyl-1H-pyrazole-4-carbonyl chloride (458 mg, 2.35 mmol) was dissolved in abs. Dichloromethane (5ml) and added dropwise to a solution of pyrrolidine-1-amine (203mg, 2.35mmol) cooled to 0 ° C and triethylamine (0.39ml, 2.82mmol) in dichloromethane (10ml) under argon. The resulting
Reaktionsgemisch wurde 30 Minuten lang bei Raumtemperatur nachgerührt und danach mit Wasser und Dichlormethan versetzt. Die wäßrige Phase wurde mehrfach intensiv mit Dichlormethan extrahiert, und die vereinigten organischen Phasen wurden danach über Magnesiumsulfat getrocknet, filtriert und eingeengt. Durch abschließende saulenchromatographische Reinigung des resultierenden Rohproduktes konnte 3- (Difluormethyl)-1 -methyl-N-(pyrrolidin-1 -yl)-1 H-pyrazol-4-carboxamid in Form eines farblosen Feststoffs isoliert werden (500 mg, 83% der Theorie). 3-(Difluormethyl)-1 - methyl-N-(pyrrolidin-1 -yl)-1 H-pyrazol-4-carboxamid (130 mg, 0.53 mmol) wurde in abs. Tetrahydrofuran (5 ml) unter Argon gelöst und bei Raumtemperatur mit Natriumhydrid (47 mg, 1 .17 mmol, 60%ige Reinheit) versetzt. Nach 30 Minuten Rühren bei The reaction mixture was stirred for 30 minutes at room temperature and then treated with water and dichloromethane. The aqueous phase was repeatedly extracted intensively with dichloromethane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. By final column chromatography purification of the resulting crude product, 3- (difluoromethyl) -1-methyl-N- (pyrrolidin-1-yl) -1H-pyrazole-4-carboxamide was isolated as a colorless solid (500 mg, 83% of Theory). 3- (Difluoromethyl) -1-methyl-N- (pyrrolidin-1-yl) -1H-pyrazole-4-carboxamide (130 mg, 0.53 mmol) was dissolved in abs. Tetrahydrofuran (5 ml) was dissolved under argon and treated at room temperature with sodium hydride (47 mg, 1 .17 mmol, 60% pure). After stirring for 30 minutes
Raumtemperatur erfolgte die Zugabe von Picolylchlo d-Hydrochlorid (87 mg, 0.53 mmol), und das resultierende Reaktionsgemisch wurde knapp 3 Stunden lang unter Rückflußbedingungen gerührt. Nach dem Abkühlen auf Raumtemperatur wurden ges. Natriumhydrogencarbonat-Lösung, Wasser und Dichlormethan zugegeben. Die wäßrige Phase wurde mehrfach intensiv mit Dichlormethan extrahiert, und die vereinigten organischen Phasen wurden danach über Magnesiumsulfat getrocknet, filtriert und eingeengt. Durch abschließende säulenchromatographische Reinigung des resultierenden Rohproduktes konnte 3-(Difluormethyl)-1 -methyl-N-(pyridin-2-ylmethyl)- N-(pyrrolidin-1 -yl)-1 H-pyrazol-4-carboxamid in Form eines zähen Öls isoliert werden (73 mg, 41 % der Theorie). 1H-NMR (400 MHz, CDCIs δ, ppm) 8.59 (m, 1 H), 7.69 (m, 1 H), 7.66 (m, 1 H), 7.48 (m, 1 H), 7.31 -7.27 (m, 1 H), 7.24-6.97 (br. t, 1 H, CHF2), 5.19 (s, 2H), 4.13-4.08 (m, 2H), 3.90 (s, 3H), 3.70-3.62 (m, 2H), 2.28-2.21 (m, 2H), 2.10-2.03 (m, 2H). Room temperature, the addition of picolylchloro-hydrochloride (87 mg, 0.53 mmol) and the resulting reaction mixture was stirred under reflux conditions for almost 3 hours. After cooling to room temperature, sat. Sodium bicarbonate solution, water and dichloromethane added. The aqueous phase was repeatedly extracted intensively with dichloromethane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography of the resulting crude product gave 3- (difluoromethyl) -1-methyl-N- (pyridin-2-ylmethyl) -N- (pyrrolidin-1-yl) -1H-pyrazole-4-carboxamide as a viscous substance Oil are isolated (73 mg, 41% of theory). 1 H-NMR (400 MHz, CDCls δ, ppm) 8.59 (m, 1H), 7.69 (m, 1H), 7.66 (m, 1H), 7.48 (m, 1H), 7.31-7.27 (m , 1H), 7.24-6.97 (br t, 1H, CHF 2 ), 5.19 (s, 2H), 4.13-4.08 (m, 2H), 3.90 (s, 3H), 3.70-3.62 (m, 2H), 2.28-2.21 (m, 2H), 2.10-2.03 (m, 2H).
No. A20-36: N-{[3-Chlor-5-(trifluormethyl)pyridin-2-yl]methyl}-3-(difluormethyl)-1 - methyl-N-(pyrrolidin-1 -yl)-1 H-pyrazol-4-carboxamid No. A20-36: N - {[3-Chloro-5- (trifluoromethyl) pyridin-2-yl] methyl} -3- (difluoromethyl) -1-methyl-N- (pyrrolidin-1-yl) -1H-pyrazole -4-carboxamide
3-(Difluormethyl)-1 -methyl-1 H-pyrazol-4-carbonylchlorid (458 mg, 2.35 mmol) wurde in abs. Dichlormethan (5 ml) gelöst und tropfenweise zu einer auf 0 °C eingekühlten3- (Difluoromethyl) -1-methyl-1H-pyrazole-4-carbonyl chloride (458 mg, 2.35 mmol) was dissolved in abs. Dichloromethane (5 ml) and added dropwise to a cooled to 0 ° C.
Lösung von Pyrrolidin-1 -amin (203 mg, 2.35 mmol) sowie Triethylamin (0.39 ml, 2.82 mmol) in Dichlormethan (10 ml) unter Argon gegeben wurde. Das resultierende Solution of pyrrolidine-1-amine (203 mg, 2.35 mmol) and triethylamine (0.39 mL, 2.82 mmol) in dichloromethane (10 mL) under argon. The resulting
Reaktionsgemisch wurde 30 Minuten lang bei Raumtemperatur nachgerührt und danach mit Wasser und Dichlormethan versetzt. Die wäßrige Phase wurde mehrfach intensiv mit Dichlormethan extrahiert, und die vereinigten organischen Phasen wurden danach über Magnesiumsulfat getrocknet, filtriert und eingeengt. Durch abschließende saulenchromatographische Reinigung des resultierenden Rohproduktes konnte 3- (Difluormethyl)-1 -methyl-N-(pyrrolidin-1 -yl)-1 H-pyrazol-4-carboxamid in Form eines farblosen Feststoffs isoliert werden (500 mg, 83% der Theorie). 3-(Difluormethyl)-1 - methyl-N-(pyrrolidin-1 -yl)-1 H-pyrazol-4-carboxamid (100 mg, 0.41 mmol) wurde in abs. Aceton (15 ml) unter Argon gelöst und bei Raumtemperatur mit Kaliumcarbonat (1 13 mg, 0.82 mmol) sowie katalytischen mengen an Ν,Ν-Dimethylformamid versetzt. Nach 30 Minuten Rühren bei Raumtemperatur erfolgte die Zugabe von Picolyichlorid (94 mg, 0.41 mmol), und das resultierende Reaktionsgemisch wurde knapp 6 Stunden lang unter Rückflußbedingungen gerührt. Nach dem Abkühlen auf Raumtemperatur wurden ges. Natriumhydrogencarbonat-Lösung, Wasser und Dichlormethan zugegeben. Die wäßrige Phase wurde mehrfach intensiv mit Dichlormethan extrahiert, und die vereinigten organischen Phasen wurden danach über Magnesiumsulfat getrocknet, filtriert und eingeengt. Durch abschließende säulenchromatographische Reinigung des resultierenden Rohproduktes konnte N-{[3-Chlor-5-(trifluormethyl)pyridin-2-yl]methyl}- 3-(difluormethyl)-1 -methyl-N-(pyrrolidin-1 -yl)-1 H-pyrazol-4-carboxamid in Form eines farblosen Feststoffs isoliert werden (83 mg, 46% der Theorie). 1H-NMR (400 MHz, CDCIs δ, ppm) 8.78 (m, 1 H), 8.49 (m, 1 H), 8.05 (m, 1 H), 7.21 -6.94 (br. t, 1 H, CHF2), 5.45 (s, 2H), 4.75-4.70 (m, 2H), 4.21 -4.14 (m, 2H), 3.93 (s, 3H), 2.47-2.41 (m, 2H), 2.38-2.30 (m, 2H). The reaction mixture was stirred for 30 minutes at room temperature and then treated with water and dichloromethane. The aqueous phase was repeatedly extracted intensively with dichloromethane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. By final column chromatography purification of the resulting crude product, 3- (difluoromethyl) -1-methyl-N- (pyrrolidin-1-yl) -1H-pyrazole-4-carboxamide was isolated as a colorless solid (500 mg, 83% of Theory). 3- (Difluoromethyl) -1-methyl-N- (pyrrolidin-1-yl) -1H-pyrazole-4-carboxamide (100 mg, 0.41 mmol) was dissolved in abs. Dissolved acetone (15 ml) under argon and treated at room temperature with potassium carbonate (1 13 mg, 0.82 mmol) and catalytic amounts of Ν, Ν-dimethylformamide. After stirring at room temperature for 30 minutes, picolychloride (94 mg, 0.41 mmol) was added and the resulting reaction mixture was stirred under reflux conditions for almost 6 hours. After cooling to room temperature, sat. Sodium bicarbonate solution, water and dichloromethane added. The aqueous phase was repeatedly extracted intensively with dichloromethane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. By final column chromatographic purification of the N - {[3-chloro-5- (trifluoromethyl) pyridin-2-yl] methyl} -3- (difluoromethyl) -1-methyl-N- (pyrrolidin-1-yl) -1H-pyrazole 4-carboxamide in the form of a colorless solid isolated (83 mg, 46% of theory). 1 H-NMR (400 MHz, CDCIs δ, ppm) 8.78 (m, 1H), 8.49 (m, 1H), 8.05 (m, 1H), 7.21-6.94 (br.t, 1H, CHF 2 ), 5.45 (s, 2H), 4.75-4.70 (m, 2H), 4.21-4.14 (m, 2H), 3.93 (s, 3H), 2.47-2.41 (m, 2H), 2.38-2.30 (m, 2H ).
No. A24-21 : 3-(Difluormethyl)-1 -ethyl-5-fluor-N-(pyridin-2-ylmethyl)-N-(pyrrolidin-1 -yl)- 1 H-pyrazol-4-carboxamid No. A24-21: 3- (Difluoromethyl) -1-ethyl-5-fluoro-N- (pyridin-2-ylmethyl) -N- (pyrrolidin-1-yl) -1 H -pyrazole-4-carboxamide
5-Fluor-3-(difluormethyl)-1 -ethyl-1 H-pyrazol-4-carbonsäure (200 mg, 0.96 mmol) wurde in abs. Dichlormethan (20 ml) gelöst und mit Triethylamin (0.40 ml, 2.88 mmol) versetzt. Nach 5 Minuten Rühren bei Raumtemperatur erfolgte die Zugabe von 5-Fluoro-3- (difluoromethyl) -1-ethyl-1H-pyrazole-4-carboxylic acid (200 mg, 0.96 mmol) was dissolved in abs. Dissolved dichloromethane (20 ml) and triethylamine (0.40 ml, 2.88 mmol) was added. After stirring for 5 minutes at room temperature, the addition of
Pyrrolidin-1 -amin (99 mg, 1 .15 mmol) und von 2,4,6-Tripropyl-1 ,3,5,2,4,6- trioxatriphosphorinan-2,4,6-trioxid (0.86 ml, 1 .44 mmol, 50% Lösung in Pyrrolidine-1-amine (99 mg, 1.15 mmol) and 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide (0.86 ml, 1 .44 mmol, 50% solution in
Tetrahydrofuran). Das resultierende Reaktionsgemisch wurde 30 Minuten lang bei Raumtemperatur nachgerührt und danach mit Wasser, ges. Tetrahydrofuran). The resulting reaction mixture was stirred for 30 minutes at room temperature and then washed with water, sat.
Natriumhydrogencarbonatlösung und Dichlormethan versetzt. Die wäßrige Phase wurde mehrfach intensiv mit Dichlormethan extrahiert, und die vereinigten organischen Phasen wurden danach über Magnesiumsulfat getrocknet, filtriert und eingeengt. Durch abschließende säulenchromatographische Reinigung des resultierenden Rohproduktes konnte 3-(Difluormethyl)-1 -ethyl-5-fluor-N-(pyrrolidin-1 -yl)-1 H-pyrazol-4- carboxamid in Form eines farblosen Feststoffs isoliert werden (309 mg, 86% der Theorie). 1H-NMR (400 MHz, CDCIs δ, ppm) 7.08-6.94 (br. t, 1 H, CHF2) 6.81 (br. s, 1 H, NH), 4.15-4.10 (q, 2H), 2.99 (m, 4H), 1 .90 (m, 4H), 1 .47 (t, 3H). 3-(Difluormethyl)- 1 -ethyl-5-fluor-N-(pyrrolidin-1 -yl)-1 H-pyrazol-4-carboxamid (130 mg, 0.47 mmol) wurde in abs. Tetrahydrofuran (5 ml) unter Argon gelöst und bei Raumtemperatur mit Sodium bicarbonate solution and dichloromethane. The aqueous phase was repeatedly extracted intensively with dichloromethane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography of the resulting crude product afforded 3- (difluoromethyl) -1-ethyl-5-fluoro-N- (pyrrolidin-1-yl) -1H-pyrazole-4-carboxamide as a colorless solid (309 mg , 86% of the theory). 1 H-NMR (400 MHz, CDCIs δ, ppm) 7.08-6.94 (br.t, 1H, CHF 2 ) 6.81 (br.s, 1H, NH), 4.15-4.10 (q, 2H), 2.99 ( m, 4H), 1 .90 (m, 4H), 1 .47 (t, 3H). 3- (Difluoromethyl) -1-ethyl-5-fluoro-N- (pyrrolidin-1-yl) -1H-pyrazole-4-carboxamide (130 mg, 0.47 mmol) was dissolved in abs. Tetrahydrofuran (5 ml) was dissolved under argon and at room temperature with
Natriumhydrid (41 mg, 1 .02 mmol, 60%ige Reinheit) versetzt. Nach 30 Minuten Rühren bei Raumtemperatur erfolgte die Zugabe von Picolylchlorid (HCI-Salz, 77 mg, 0.47 mmol), und das resultierende Reaktionsgemisch wurde ca. 3 Stunden lang unter Rückflußbedingungen gerührt. Nach dem Abkühlen auf Raumtemperatur wurden ges. Natriumhydrogencarbonat-Lösung, Wasser und Dichlormethan zugegeben. Die wäßrige Phase wurde mehrfach intensiv mit Dichlormethan extrahiert, und die vereinigten organischen Phasen wurden danach über Magnesiumsulfat getrocknet, filtriert und eingeengt. Durch abschließende saulenchromatographische Reinigung des resultierenden Rohproduktes konnte 3-(Difluormethyl)-1 -ethyl-5-fluor-N-(pyridin-2- ylmethyl)-N-(pyrrolidin-1 -yl)-1 H-pyrazol-4-carboxamid in Form eines farblosen Sodium hydride (41 mg, 1 .02 mmol, 60% purity) was added. After stirring for 30 minutes at room temperature, the addition of picolyl chloride (HCl salt, 77 mg, 0.47 mmol), and the resulting reaction mixture was stirred for about 3 hours under reflux conditions. After cooling to room temperature, sat. Sodium bicarbonate solution, water and dichloromethane added. The aqueous phase was repeatedly extracted intensively with dichloromethane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column of the resulting crude product afforded 3- (difluoromethyl) -1-ethyl-5-fluoro-N- (pyridin-2-ylmethyl) -N- (pyrrolidin-1-yl) -1H-pyrazole-4-carboxamide in the form of a colorless
Feststoffs isoliert werden (86 mg, 49% der Theorie). 1H-NMR (400 MHz, CDCIs δ, ppm) 8.60 (m, 1 H), 7.68 (m, 1 H), 7.54 (m, 1 H), 7.30 (m, 1 H), 7.1 1 -6.83 (br. t, 1 H,Be isolated solid (86 mg, 49% of theory). 1 H-NMR (400 MHz, CDCl3 δ, ppm) 8.60 (m, 1H), 7.68 (m, 1H), 7.54 (m, 1H), 7.30 (m, 1H), 7.1 1 -6.83 ( br, t, 1 H,
CHF2), 5.19 (s, 2H), 4.17-4.05 (m, 4H), 3.65-3.58 (m, 2H), 2.28-2.22 (m, 2H), 2.09-2.04 (m, 2H), 1 .43 (t, 3H). CHF 2 ), 5.19 (s, 2H), 4.17-4.05 (m, 4H), 3.65-3.58 (m, 2H), 2.28-2.22 (m, 2H), 2.09-2.04 (m, 2H), 1 .43 (t, 3H).
No. B3-61 : N-(2-Cyanobenzyl)-2-(difluormethyl)-N',N'-dimethylthiophen-3- carbohydrazid No. B3-61: N- (2-cyanobenzyl) -2- (difluoromethyl) -N ', N'-dimethylthiophene-3-carbohydrazide
2-(Difluormethyl)thiophen-3-carbonsäure (600 mg, 3.37 mmol) wurde in abs. 2- (Difluoromethyl) thiophene-3-carboxylic acid (600 mg, 3.37 mmol) was dissolved in abs.
Dichlormethan (20 ml) gelöst und mit Triethylamin (1 .41 ml, 10.10 mmol) versetzt. Nach 5 Minuten Rühren bei Raumtemperatur erfolgte die Zugabe von N,N- Dimethylhydrazin (0.31 ml, 4.04 mmol) und von 2,4,6-Tripropyl-1 ,3,5,2,4,6- trioxatriphosphorinan-2,4,6-trioxid (3.01 ml, 5.05 mmol, 50% Lösung in Dissolved dichloromethane (20 ml) and treated with triethylamine (1 .41 ml, 10.10 mmol). After stirring for 5 minutes at room temperature, N, N-dimethylhydrazine (0.31 ml, 4.04 mmol) and 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphorinan-2,4 were added, 6-trioxide (3.01 ml, 5.05 mmol, 50% solution in
Tetrahydrofuran). Das resultierende Reaktionsgemisch wurde 30 Minuten lang bei Raumtemperatur nachgerührt und danach mit Wasser, ges. Tetrahydrofuran). The resulting reaction mixture was stirred for 30 minutes at room temperature and then washed with water, sat.
Natriumhydrogencarbonatlösung und Dichlormethan versetzt. Die wäßrige Phase wurde mehrfach intensiv mit Dichlormethan extrahiert, und die vereinigten organischen Phasen wurden danach über Magnesiumsulfat getrocknet, filtriert und eingeengt. Durch abschließende säulenchromatographische Reinigung des resultierenden Rohproduktes konnte 2-(Difluormethyl)-N',N'-dimethylthiophen-3-carbohydrazid in Form eines farblosen Feststoffs isoliert werden (760 mg, 97% der Theorie). 1H-NMR (400 MHz, CDCIs δ, ppm) 7.99 (m, 1 H), 7.27 (m, 1 H), 6.98-6.70 (br. t, 1 H, CHF2) 6.56 (br. s, 1 H, NH), 2.66 (s, 6H). 2-(Difluormethyl)-N',N'-dimethylthiophen-3-carbohydrazid (130 mg, 0.59 mmol) wurde in abs. Tetrahydrofuran (5 ml) unter Argon gelöst und bei Raumtemperatur mit Natriumhydrid (28 mg, 0.71 mmol, 60%ige Reinheit) versetzt. Nach 30 Minuten Rühren bei Raumtemperatur erfolgte die Zugabe von 2-Sodium bicarbonate solution and dichloromethane. The aqueous phase was repeatedly extracted intensively with dichloromethane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography of the resulting crude product allowed 2- (difluoromethyl) -N ', N'-dimethylthiophene-3-carbohydrazide to be isolated as a colorless solid (760 mg, 97% of theory). 1 H-NMR (400 MHz, CDCIs δ, ppm) 7.99 (m, 1H), 7.27 (m, 1H), 6.98-6.70 (br t, 1H, CHF 2 ) 6.56 (br s, 1H, NH) , 2.66 (s, 6H). 2- (Difluoromethyl) -N ', N'-dimethylthiophene-3-carbohydrazide (130 mg, 0.59 mmol) was dissolved in abs. Tetrahydrofuran (5 ml) was dissolved under argon and treated at room temperature with sodium hydride (28 mg, 0.71 mmol, 60% pure). After stirring for 30 minutes at room temperature, the addition of 2-
Chlormethylbenzonitril (89 mg, 0.59 mmol), und das resultierende Reaktionsgemisch wurde ca. 3 Stunden lang unter Rückflußbedingungen gerührt. Nach dem Abkühlen auf Raumtemperatur wurden ges. Natriumhydrogencarbonat-Lösung, Wasser und Dichlormethan zugegeben. Die wäßrige Phase wurde mehrfach intensiv mit Chloromethylbenzonitrile (89 mg, 0.59 mmol), and the resulting reaction mixture was stirred at reflux for about 3 hours. After cooling to room temperature, sat. Sodium bicarbonate solution, water and dichloromethane added. The aqueous phase was repeatedly intensively with
Dichlormethan extrahiert, und die vereinigten organischen Phasen wurden danach über Magnesiumsulfat getrocknet, filtriert und eingeengt. Durch abschließende säulenchromatographische Reinigung des resultierenden Rohproduktes konnte N-(2- Cyanobenzyl)-2-(difluormethyl)-N',N'-dimethylthiophen-3-carbohydrazid in Form eines zähen Öls isoliert werden (1 13 mg, 57% der Theorie). 1H-NMR (400 MHz, CDCIs δ, ppm) 7.89 (m, 1 H), 7.76 (m, 1 H), 7.67 (m, 1 H), 7.58 (m, 1 H), 7.49 (m, 1 H), 7.18 (m, 1 H), 6.92-6.64 (br. t, 1 H, CHF2), 5.16 (s, 2H), 2.50 (s, 6H). Dichloromethane extracted, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography of the resulting crude product gave N- (2-cyanobenzyl) -2- (difluoromethyl) -N ', N'-dimethylthiophene-3-carbohydrazide as a viscous oil (1 13 mg, 57% of theory). , 1 H-NMR (400 MHz, CDCl3 δ, ppm) 7.89 (m, 1H), 7.76 (m, 1H), 7.67 (m, 1H), 7.58 (m, 1H), 7.49 (m, 1 H), 7.18 (m, 1H), 6.92-6.64 (br t, 1H, CHF 2 ), 5.16 (s, 2H), 2.50 (s, 6H).
No. C4-21 : 2-Methyl-N-(pyridin-2-ylmethyl)-N-(pyrrolidin-1 -yl)-3-furamid No. C4-21: 2-methyl-N- (pyridin-2-ylmethyl) -N- (pyrrolidin-1-yl) -3-furamide
2-Methyl-3-furoylchlorid (500 mg, 3.46 mmol) wurde in abs. Dichlormethan (5 ml) gelöst und tropfenweise zu einer auf 0 °C eingekühlten Lösung von Pyrrolidin-1 -amin (298 mg, 3.46 mmol) sowie Triethylamin (0.58 ml, 4.15 mmol) in Dichlormethan (10 ml) unter Argon gegeben wurde. Das resultierende Reaktionsgemisch wurde 30 Minuten lang bei Raumtemperatur nachgerührt und danach mit Wasser und Dichlormethan versetzt. Die wäßrige Phase wurde mehrfach intensiv mit Dichlormethan extrahiert, und die vereinigten organischen Phasen wurden danach über Magnesiumsulfat getrocknet, filtriert und eingeengt. Durch abschließende säulenchromatographische Reinigung des resultierenden Rohproduktes konnte 2-Methyl-N-(pyrrolidin-1 -yl)-3- furamid in Form eines farblosen Feststoffs isoliert werden (290 mg, 43% der Theorie). 2-Methyl-N-(pyrrolidin-1 -yl)-3-furamid (140 mg, 0.72 mmol) wurde in abs. 2-Methyl-3-furoyl chloride (500 mg, 3.46 mmol) was dissolved in abs. Dichloromethane (5ml) and added dropwise to a solution of pyrrolidine-1-amine (298mg, 3.46mmol) cooled to 0 ° C and triethylamine (0.58ml, 4.15mmol) in dichloromethane (10ml) under argon. The resulting reaction mixture was stirred for 30 minutes at room temperature and then treated with water and dichloromethane. The aqueous phase was repeatedly extracted intensively with dichloromethane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography of the resulting crude product gave 2-methyl-N- (pyrrolidin-1-yl) -3- Furamid be isolated in the form of a colorless solid (290 mg, 43% of theory). 2-Methyl-N- (pyrrolidin-1-yl) -3-furamide (140 mg, 0.72 mmol) was dissolved in abs.
Tetrahydrofuran (5 ml) unter Argon gelöst und bei Raumtemperatur mit Natriumhydrid (63 mg, 1 .59 mmol, 60%ige Reinheit) versetzt. Nach 30 Minuten Rühren bei Tetrahydrofuran (5 ml) was dissolved under argon and treated at room temperature with sodium hydride (63 mg, 1 .59 mmol, 60% pure). After stirring for 30 minutes
Raumtemperatur erfolgte die Zugabe von Picolylchlo d-Hydrochlorid (1 18 mg, 0.72 mmol), und das resultierende Reaktionsgemisch wurde knapp 3 Stunden lang unter Rückflußbedingungen gerührt. Nach dem Abkühlen auf Raumtemperatur wurden ges. Natriumhydrogencarbonat-Lösung, Wasser und Dichlormethan zugegeben. Die wäßrige Phase wurde mehrfach intensiv mit Dichlormethan extrahiert, und die vereinigten organischen Phasen wurden danach über Magnesiumsulfat getrocknet, filtriert und eingeengt. Durch abschließende saulenchromatographische Reinigung des resultierenden Rohproduktes konnte 2-Methyl-N-(pyridin-2-ylmethyl)-N-(pyrrolidin-1 - yl)-3-furamid in Form eines zähen Öls isoliert werden (62 mg, 30% der Theorie). 1H- NMR (400 MHz, CDCIs δ, ppm) 8.59 (m, 1 H), 7.67 (m, 1 H), 7.54 (m, 1 H), 7.29 (m, 1 H), 7.14 (m, 1 H), 6.55 (m, 1 H), 5.22 (s, 2H), 4.13-4.08 (m, 2H), 3.73-3.67 (m, 2H), 2.42 (s, 3H), 2.29-2.22 (m, 2H), 2.09-2.02 (m, 2H). Room temperature, the addition of picolylchloro-hydrochloride (1 18 mg, 0.72 mmol) was performed, and the resulting reaction mixture was stirred under reflux conditions for almost 3 hours. After cooling to room temperature, sat. Sodium bicarbonate solution, water and dichloromethane added. The aqueous phase was repeatedly extracted intensively with dichloromethane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column of the resulting crude product gave 2-methyl-N- (pyridin-2-ylmethyl) -N- (pyrrolidin-1-yl) -3-fureamine as a viscous oil (62 mg, 30% of theory ). 1 H-NMR (400 MHz, CDCl3 δ, ppm) 8.59 (m, 1H), 7.67 (m, 1H), 7.54 (m, 1H), 7.29 (m, 1H), 7.14 (m, 1 H), 6.55 (m, 1H), 5.22 (s, 2H), 4.13-4.08 (m, 2H), 3.73-3.67 (m, 2H), 2.42 (s, 3H), 2.29-2.22 (m, 2H ), 2.09-2.02 (m, 2H).
No. D1 -21 : N',N',4-Trimethyl-2-(pyridin-3-yl)-N-(pyridin-2-ylmethyl)-1 ,3-thiazol-5- carbohydrazid No. D1 -21: N ', N', 4-trimethyl-2- (pyridin-3-yl) -N- (pyridin-2-ylmethyl) -1, 3-thiazole-5-carbohydrazide
4-Methyl-2-(pyridin-3-yl)-1 ,3-thiazol-5-carbonsäure (700 mg, 3.18 mmol) wurde in abs. Dichlormethan (20 ml) gelöst und mit Triethylamin (1 .33 ml, 9.54 mmol) versetzt. Nach 5 Minuten Rühren bei Raumtemperatur erfolgte die Zugabe von N,N-Dimethylhydrazin (0.29 ml, 3.81 mmol) und von 2,4,6-Tripropyl-1 ,3,5,2,4,6-trioxatriphosphorinan-2,4,6- trioxid (3.03 g, 4.76 mmol, 50% Lösung in Tetrahydrofuran). Das resultierende 4-Methyl-2- (pyridin-3-yl) -1,3-thiazole-5-carboxylic acid (700 mg, 3.18 mmol) was dissolved in abs. Dissolved dichloromethane (20 ml) and treated with triethylamine (1 .33 ml, 9.54 mmol). After stirring for 5 minutes at room temperature, N, N-dimethylhydrazine (0.29 ml, 3.81 mmol) and 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphorinan-2,4 were added, 6-trioxide (3.03 g, 4.76 mmol, 50% solution in tetrahydrofuran). The resulting
Reaktionsgemisch wurde 30 Minuten lang bei Raumtemperatur nachgerührt und danach mit Wasser, ges. Natriumhydrogencarbonatlösung und Dichlormethan versetzt. Die wäßrige Phase wurde mehrfach intensiv mit Dichlormethan extrahiert, und die vereinigten organischen Phasen wurden danach über Magnesiumsulfat getrocknet, filtriert und eingeengt. Durch abschließende säulenchromatographische Reinigung des resultierenden Rohproduktes konnte N',N',4-Trimethyl-2-(pyridin-3-yl)- 1 ,3-thiazol-5-carbohydrazid in Form eines farblosen Feststoffs isoliert werden (683 mg, 82% der Theorie). 1H-NMR (400 MHz, CDCIs δ, ppm) 9.20 (m, 1 H), 8.68 (m, 1 H), 8.33- 8.29 (m, 1 H), 7.41 (m, 1 H), 6.25 (br. s, 1 H, NH), 2.88 (s, 3H), 2.66 (s, 6H). Ν',Ν',4- Trimethyl-2-(pyridin-3-yl)-1 ,3-thiazol-5-carbohydrazid (120 mg, 0.46 mmol) wurde in abs. Tetrahydrofuran (5 ml) unter Argon gelöst und bei Raumtemperatur mit The reaction mixture was stirred for 30 minutes at room temperature and then washed with water, sat. Sodium bicarbonate solution and dichloromethane. The aqueous phase was repeatedly extracted intensively with dichloromethane, and the combined organic phases were then washed over magnesium sulfate dried, filtered and concentrated. Final purification by column chromatography of the resulting crude product isolated N ', N', 4-trimethyl-2- (pyridin-3-yl) -1,3-thiazole-5-carbohydrazide as a colorless solid (683 mg, 82%). the theory). 1 H-NMR (400 MHz, CDCl3 δ, ppm) 9.20 (m, 1H), 8.68 (m, 1H), 8.33-8.29 (m, 1H), 7.41 (m, 1H), 6.25 (br s, 1 H, NH), 2.88 (s, 3H), 2.66 (s, 6H). Ν ', Ν', 4-trimethyl-2- (pyridin-3-yl) -1,3-thiazole-5-carbohydrazide (120 mg, 0.46 mmol) was dissolved in abs. Tetrahydrofuran (5 ml) was dissolved under argon and at room temperature with
Natriumhydrid (40 mg, 1 .01 mmol, 60%ige Reinheit) versetzt. Nach 30 Minuten Rühren bei Raumtemperatur erfolgte die Zugabe von Picolylchlorid-Hydrochlorid (75 mg, 0.46 mmol), und das resultierende Reaktionsgemisch wurde ca. 3 Stunden lang unterSodium hydride (40 mg, 1 .01 mmol, 60% purity) was added. After stirring for 30 minutes at room temperature, picolyl chloride hydrochloride (75 mg, 0.46 mmol) was added and the resulting reaction mixture was allowed to stand for about 3 hours
Rückflußbedingungen gerührt. Nach dem Abkühlen auf Raumtemperatur wurden ges. Natriumhydrogencarbonat-Lösung, Wasser und Dichlormethan zugegeben. Die wäßrige Phase wurde mehrfach intensiv mit Dichlormethan extrahiert, und die vereinigten organischen Phasen wurden danach über Magnesiumsulfat getrocknet, filtriert und eingeengt. Durch abschließende säulenchromatographische Reinigung des resultierenden Rohproduktes konnte N',N',4-Trimethyl-2-(pyridin-3-yl)-N-(pyridin-2- ylmethyl)-1 ,3-thiazol-5-carbohydrazid in Form eines zähen Öls isoliert werden (92 mg, 57% der Theorie). 1H-NMR (400 MHz, CDCIs δ, ppm) 9.12 (m, 1 H), 8.63 (m, 1 H), 8.23 (m, 1 H), 7.87 (m, 1 H), 7.78 (m, 1 H), 7.69-7.65 (m, 1 H), 7.61 -7.58 (m, 1 H), 7.39-7.34 (m, 1 H), 5.22 (s, 2H), 3.50 (s, 6H), 2.77 (s, 3H). Reflux conditions stirred. After cooling to room temperature, sat. Sodium bicarbonate solution, water and dichloromethane added. The aqueous phase was repeatedly extracted intensively with dichloromethane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography of the resulting crude product gave N ', N', 4-trimethyl-2- (pyridin-3-yl) -N- (pyridin-2-ylmethyl) -1,3-thiazole-5-carbohydrazide as a viscous oil (92 mg, 57% of theory). 1 H-NMR (400 MHz, CDCl3 δ, ppm) 9.12 (m, 1H), 8.63 (m, 1H), 8.23 (m, 1H), 7.87 (m, 1H), 7.78 (m, 1 H), 7.69-7.65 (m, 1H), 7.61-7.58 (m, 1H), 7.39-7.34 (m, 1H), 5.22 (s, 2H), 3.50 (s, 6H), 2.77 (s , 3H).
No. E5-21 : 3,4-Dichlor-N-(pyridin-2-ylmethyl)-N-(pyrrolidin-1 -yl)-1 ,2-thiazol-5- carboxamid No. E5-21: 3,4-dichloro-N- (pyridin-2-ylmethyl) -N- (pyrrolidin-1-yl) -1,2-thiazole-5-carboxamide
3,4-Dichlorisothiazol-5-ylcarbonsäure (400 mg, 2.02 mmol) wurde in abs. 3,4-dichloroisothiazol-5-ylcarboxylic acid (400 mg, 2.02 mmol) was dissolved in abs.
Dichlormethan (20 ml) gelöst und mit Triethylamin (0.85 ml, 6.06 mmol) versetzt. Nach 5 Minuten Rühren bei Raumtemperatur erfolgte die Zugabe von Pyrrolidin-1 -amin (209 mg, 2.42 mmol) und von 2,4,6-Tripropyl-1 ,3,5,2,4,6-trioxatriphosphorinan-2,4,6-trioxid (1 .80 ml, 3.03 mmol, 50% Lösung in Tetrahydrofuran). Das resultierende Reaktionsgemisch wurde 30 Minuten lang bei Raumtemperatur nachgerührt und danach mit Wasser, ges. Natriumhydrogencarbonatlösung und Dichlormethan versetzt. Die wäßrige Phase wurde mehrfach intensiv mit Dichlormethan extrahiert, und die vereinigten organischen Phasen wurden danach über Magnesiumsulfat getrocknet, filtriert und eingeengt. Durch abschließende säulenchromatographische Reinigung des resultierenden Rohproduktes konnte 3,4-Dichlor-N-(pyrrolidin-1 -yl)-1 ,2- thiazol-5-carboxamid in Form eines farblosen Feststoffs isoliert werden (520 mg, 92% der Theorie). 1H-NMR (400 MHz, CDCIs δ, ppm) 6.75 (br. s, 1 H, NH), 3.38-3.28 (m, 2H), 2.73-2.64 (m, 2H), 2.03-1 .98 (m, 4H). 3,4-Dichlor-N-(pyrrolidin-1 -yl)-1 ,2-thiazol-5- carboxamid (120 mg, 0.45 mmol) wurde in abs. Tetrahydrofuran (5 ml) unter Argon gelöst und bei Raumtemperatur mit Natriumhydrid (40 mg, 1 .99 mmol, 60%ige Dissolved dichloromethane (20 ml) and treated with triethylamine (0.85 ml, 6.06 mmol). After stirring at room temperature for 5 minutes, pyrrolidine-1-amine (209 mg, 2.42 mmol) and 2,4,6-tripropyl-1, 3,5,2,4,6-trioxatriphosphorinane-2,4 were added, 6-trioxide (1 .80 ml, 3.03 mmol, 50% solution in tetrahydrofuran). The resulting The reaction mixture was stirred for 30 minutes at room temperature and then washed with water, sat. Sodium bicarbonate solution and dichloromethane. The aqueous phase was repeatedly extracted intensively with dichloromethane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography of the resulting crude product gave 3,4-dichloro-N- (pyrrolidin-1-yl) -1,2-thiazole-5-carboxamide as a colorless solid (520 mg, 92% of theory). 1 H-NMR (400 MHz, CDCIs δ, ppm) 6.75 (br.s, 1H, NH), 3.38-3.28 (m, 2H), 2.73-2.64 (m, 2H), 2.03-1 .98 (m , 4H). 3,4-Dichloro-N- (pyrrolidin-1-yl) -1,2-thiazole-5-carboxamide (120 mg, 0.45 mmol) was dissolved in abs. Tetrahydrofuran (5 ml) was dissolved under argon and washed at room temperature with sodium hydride (40 mg, 1 .99 mmol, 60%
Reinheit) versetzt. Nach 30 Minuten Rühren bei Raumtemperatur erfolgte die Zugabe von Picolylchlorid (HCI-Salz, 74 mg, 0.45 mmol), und das resultierende Purity). After stirring for 30 minutes at room temperature, the addition of picolyl chloride (HCl salt, 74 mg, 0.45 mmol) and the resulting
Reaktionsgemisch wurde ca. 3 Stunden lang unter Rückflußbedingungen gerührt. Nach dem Abkühlen auf Raumtemperatur wurden ges. Natriumhydrogencarbonat- Lösung, Wasser und Dichlormethan zugegeben. Die wäßrige Phase wurde mehrfach intensiv mit Dichlormethan extrahiert, und die vereinigten organischen Phasen wurden danach über Magnesiumsulfat getrocknet, filtriert und eingeengt. Durch abschließende säulenchromatographische Reinigung des resultierenden Rohproduktes konnte 3,4- Dichlor-N-(pyridin-2-ylmethyl)-N-(pyrrolidin-1 -yl)-1 ,2-thiazol-5-carboxamid in Form eines farblosen Feststoffs isoliert werden (1 12 mg, 69% der Theorie). 1H-NMR (400 MHz, CDCIs δ, ppm) 8.62 (m, 1 H), 7.71 -7.67 (m, 1 H), 7.53 (m, 1 H), 7.33 (m, 1 H), 5.15 (s, 2H), 4.18-4.13 (m, 2H), 3.71 -3.66 (m, 2H), 2.30-2.24 (m, 2H), 2.13-2.08 (m, 2H). The reaction mixture was stirred for about 3 hours under reflux conditions. After cooling to room temperature, sat. Sodium bicarbonate solution, water and dichloromethane added. The aqueous phase was repeatedly extracted intensively with dichloromethane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography of the resulting crude product allowed 3,4-dichloro-N- (pyridin-2-ylmethyl) -N- (pyrrolidin-1-yl) -1,2-thiazole-5-carboxamide to be isolated as a colorless solid (1 12 mg, 69% of theory). 1 H-NMR (400 MHz, CDCls δ, ppm) 8.62 (m, 1H), 7.71-7.67 (m, 1H), 7.53 (m, 1H), 7.33 (m, 1H), 5.15 (s , 2H), 4.18-4.13 (m, 2H), 3.71-3.66 (m, 2H), 2.30-2.24 (m, 2H), 2.13-2.08 (m, 2H).
No. F2-1 : N-(2-Chlorbenzyl)-4-isopropyl-N',N'-dimethyl-1 ,2,3-thiadiazol-5- carbohydrazid No. F2-1: N- (2-chlorobenzyl) -4-isopropyl-N ', N'-dimethyl-1, 2,3-thiadiazole-5-carbohydrazide
4-lsopropyl-1 ,2,3-thiadiazol-5-carbonsäure (600 mg, 3.48 mmol) wurde in abs. 4-Isopropyl-1,2,3-thiadiazole-5-carboxylic acid (600 mg, 3.48 mmol) was dissolved in abs.
Dichlormethan (20 ml) gelöst und mit Triethylamin (1 .46 ml, 10.45 mmol) versetzt. Nach 5 Minuten Rühren bei Raumtemperatur erfolgte die Zugabe von N,N- Dimethylhydrazin (0.32 ml, 4.18 mmol) und von 2,4,6-Tripropyl-1 ,3,5,2,4,6- trioxatriphosphorinan-2,4,6-trioxid (3.1 1 ml, 5.23 mmol, 50% Lösung in Dissolved dichloromethane (20 ml) and treated with triethylamine (1.46 ml, 10.45 mmol). After stirring for 5 minutes at room temperature, N, N-dimethylhydrazine (0.32 ml, 4.18 mmol) and 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphorinan-2,4 were added, 6-trioxide (3.1 ml, 5.23 mmol, 50% solution in
Tetrahydrofuran). Das resultierende Reaktionsgemisch wurde 30 Minuten lang bei Raumtemperatur nachgerührt und danach mit Wasser, ges. Tetrahydrofuran). The resulting reaction mixture was stirred for 30 minutes at room temperature and then washed with water, sat.
Natriumhydrogencarbonatlösung und Dichlormethan versetzt. Die wäßrige Phase wurde mehrfach intensiv mit Dichlormethan extrahiert, und die vereinigten organischen Phasen wurden danach über Magnesiumsulfat getrocknet, filtriert und eingeengt. Durch abschließende säulenchromatographische Reinigung des resultierenden Rohproduktes konnte 4-lsopropyl-N',N'-dimethyl-1 ,2,3-thiadiazol-5-carbohydrazid in Form eines farblosen Feststoffs isoliert werden (190 mg, 25% der Theorie). 1H-NMR (400 MHz, CDCIs δ, ppm) 6.53 (br. s, 1 H, NH), 4.29 (sept, 1 H), 2.68 (s, 6H), 1 .48 (d, 6H). 4-lsopropyl-N',N'-dimethyl-1 ,2,3-thiadiazol-5-carbohydrazid (130 mg, 0.61 mmol) wurde in abs. Tetrahydrofuran (5 ml) unter Argon gelöst und bei Raumtemperatur mit Natriumhydrid (29 mg, 0.73 mmol, 60%ige Reinheit) versetzt. Nach 30 Minuten Rühren bei Raumtemperatur erfolgte die Zugabe von 2-Chlorbenzylchlorid (98 mg, 0.61 mmol), und das resultierende Reaktionsgemisch wurde ca. 3 Stunden lang unter Rückflußbedingungen gerührt. Nach dem Abkühlen auf Raumtemperatur wurden ges. Natriumhydrogencarbonat-Lösung, Wasser und Dichlormethan zugegeben. Die wäßrige Phase wurde mehrfach intensiv mit Dichlormethan extrahiert, und die vereinigten organischen Phasen wurden danach über Magnesiumsulfat getrocknet, filtriert und eingeengt. Durch abschließende säulenchromatographische Reinigung des resultierenden Rohproduktes konnte N-(2-Chlorbenzyl)-4-isopropyl-N',N'-dimethyl- 1 ,2,3-thiadiazol-5-carbohydrazid in Form eines zähen Öls isoliert werden (62 mg, 30% der Theorie). 1H-NMR (400 MHz, CDCIs δ, ppm) 7.67 (m, 1 H), 7.48 (m, 1 H), 7.41 (m, 1 H), 7.33 (m, 1 H), 5.10 (s, 2H), 4.12-4.07 (sept, 1 H), 3.44 (s, 6H), 1 .48 (d, 6H). Sodium bicarbonate solution and dichloromethane. The aqueous phase was repeatedly extracted intensively with dichloromethane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography of the resulting crude product isolated 4-isopropyl-N ', N'-dimethyl-1,2,3-thiadiazole-5-carbohydrazide as a colorless solid (190 mg, 25% of theory). 1 H-NMR (400 MHz, CDCIs δ, ppm) 6.53 (br.s, 1H, NH), 4.29 (sept, 1H), 2.68 (s, 6H), 1.48 (d, 6H). 4-Isopropyl-N ', N'-dimethyl-1, 2,3-thiadiazole-5-carbohydrazide (130 mg, 0.61 mmol) was dissolved in abs. Dissolved tetrahydrofuran (5 ml) under argon and at room temperature with sodium hydride (29 mg, 0.73 mmol, 60% purity) was added. After stirring for 30 minutes at room temperature, 2-chlorobenzyl chloride (98 mg, 0.61 mmol) was added and the resulting reaction mixture was stirred at reflux for about 3 hours. After cooling to room temperature, sat. Sodium bicarbonate solution, water and dichloromethane added. The aqueous phase was repeatedly extracted intensively with dichloromethane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography of the resulting crude product gave N- (2-chlorobenzyl) -4-isopropyl-N ', N'-dimethyl-1,2,3-thiadiazole-5-carbohydrazide as a viscous oil (62 mg; 30% of theory). 1 H-NMR (400 MHz, CDCl3 δ, ppm) 7.67 (m, 1H), 7.48 (m, 1H), 7.41 (m, 1H), 7.33 (m, 1H), 5.10 (s, 2H ), 4.12-4.07 (sept, 1H), 3.44 (s, 6H), 1 .48 (d, 6H).
No. F2-27: 4-lsopropyl-N',N'-dimethyl-N-(pyrimidin-2-ylmethyl)-1 ,2,3-thiadiazol-5- carbohydrazid No. F2-27: 4-isopropyl-N ', N'-dimethyl-N- (pyrimidin-2-ylmethyl) -1, 2,3-thiadiazole-5-carbohydrazide
4-lsopropyl-N N'-dimethyl-1 ,2,3-thiadiazol-5-carbohydrazid (130 mg, 0.61 mmol) wurde in abs. Tetrahydrofuran (5 ml) unter Argon gelöst und bei Raumtemperatur mit Natriumhydrid (53 mg, 1 .34 mmol, 60%ige Reinheit) versetzt. Nach 30 Minuten Rühren bei Raumtemperatur erfolgte die Zugabe von 2-Chlormethylpyrimidin (120 mg, 1 .20 mmol), und das resultierende Reaktionsgemisch wurde ca. zweieinhalb Stunden lang unter Rückflußbedingungen gerührt. Nach dem Abkühlen auf Raumtemperatur wurden ges. Natriumhydrogencarbonat-Lösung, Wasser und Dichlormethan zugegeben. Die wäßrige Phase wurde mehrfach intensiv mit Dichlormethan extrahiert, und die vereinigten organischen Phasen wurden danach über Magnesiumsulfat getrocknet, filtriert und eingeengt. Durch abschließende saulenchromatographische Reinigung des resultierenden Rohproduktes konnte 4-lsopropyl-N',N'-dimethyl-N-(pyrimidin-2- ylmethyl)-1 ,2,3-thiadiazol-5-carbohydrazid in Form eines zähen Öls isoliert werden (78 mg, 42% der Theorie). 1H-NMR (400 MHz, CDCIs δ, ppm) 8.83 (m, 2H), 7.37 (m, 1 H), 5.18 (s, 2H), 4.07-4.01 (sept, 1 H), 3.61 (s, 6H), 1 .46 (d, 6H). 4-Isopropyl-N, N'-dimethyl-1,2,3-thiadiazole-5-carbohydrazide (130 mg, 0.61 mmol) was dissolved in abs. Tetrahydrofuran (5 ml) was dissolved under argon and treated at room temperature with sodium hydride (53 mg, 1 .34 mmol, 60% purity). After stirring at room temperature for 30 minutes, 2-chloromethylpyrimidine (120 mg, 1.20 mmol) was added and the resulting reaction mixture was stirred at reflux for about 2.5 hours. After cooling to room temperature, sat. Sodium bicarbonate solution, water and dichloromethane added. The aqueous phase was repeatedly extracted intensively with dichloromethane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column of the resulting crude product afforded 4-isopropyl-N ', N'-dimethyl-N- (pyrimidin-2-ylmethyl) -1,3,3-thiadiazole-5-carbohydrazide as a viscous oil (78 mg, 42% of theory). 1 H-NMR (400 MHz, CDCls δ, ppm) 8.83 (m, 2H), 7.37 (m, 1H), 5.18 (s, 2H), 4.07-4.01 (sept, 1H), 3.61 (s, 6H ), 1 .46 (d, 6H).
No. F2-61 : 4-lsopropyl-N',N'-dimethyl-N-(2-cyanobenzyl)-1 ,2,3-thiadiazol-5- carbohydrazid No. F2-61: 4-isopropyl-N ', N'-dimethyl-N- (2-cyanobenzyl) -1, 2,3-thiadiazole-5-carbohydrazide
4-lsopropyl-N',N'-dimethyl-1 ,2,3-thiadiazol-5-carbohydrazid (130 mg, 0.61 mmol) wurde in abs. Tetrahydrofuran (5 ml) unter Argon gelöst und bei Raumtemperatur mit Natriumhydrid (29 mg, 0.73 mmol, 60%ige Reinheit) versetzt. Nach 30 Minuten Rühren bei Raumtemperatur erfolgte die Zugabe von 2-Cyanobenzylchlorid (92 mg, 0.61 mmol), und das resultierende Reaktionsgemisch wurde ca. zweieinhalb Stunden lang unter Rückflußbedingungen gerührt. Nach dem Abkühlen auf Raumtemperatur wurden ges. Natriumhydrogencarbonat-Lösung, Wasser und Dichlormethan zugegeben. Die wäßrige Phase wurde mehrfach intensiv mit Dichlormethan extrahiert, und die vereinigten organischen Phasen wurden danach über Magnesiumsulfat getrocknet, filtriert und eingeengt. Durch abschließende säulenchromatographische Reinigung des resultierenden Rohproduktes konnte 4-lsopropyl-N',N'-dimethyl-N-(2-cyanobenzyl)- 1 ,2,3-thiadiazol-5-carbohydrazid in Form eines zähen Öls isoliert werden (30 mg, 15% der Theorie). 1H-NMR (400 MHz, CDCIs δ, ppm) 7.81 -7.77 (m, 2H), 7.65 (m, 1 H), 7.59 (m, 1 H), 5.12 (s, 2H), 4.08-4.02 (sept, 1 H), 3.50 (s, 6H), 1 .48 (d, 6H). 4-Isopropyl-N ', N'-dimethyl-1, 2,3-thiadiazole-5-carbohydrazide (130 mg, 0.61 mmol) was dissolved in abs. Dissolved tetrahydrofuran (5 ml) under argon and at room temperature with sodium hydride (29 mg, 0.73 mmol, 60% purity) was added. After stirring at room temperature for 30 minutes, 2-cyanobenzyl chloride (92 mg, 0.61 mmol) was added and the resulting reaction mixture was stirred at reflux for about 2.5 hours. After cooling to room temperature, sat. Sodium bicarbonate solution, water and dichloromethane added. The aqueous phase was repeatedly extracted intensively with dichloromethane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. By final column chromatographic purification of the resulting crude product 4-isopropyl-N ', N'-dimethyl-N- (2-cyanobenzyl) - 1, 2,3-thiadiazole-5-carbohydrazide in the form of a viscous oil were isolated (30 mg, 15% of theory) , 1 H-NMR (400 MHz, CDCls δ, ppm) 7.81-7.77 (m, 2H), 7.65 (m, 1H), 7.59 (m, 1H), 5.12 (s, 2H), 4.08-4.02 (sept , 1H), 3.50 (s, 6H), 1 .48 (d, 6H).
In Analogie zu den oben angeführten und an entsprechender Stelle rezitierten In analogy to the above and recited in the appropriate place
Herstellungsbeispielen und unter Berücksichtigung der allgemeinen Angaben zur Herstellung von substituierte Heteroarylcarbonsäurehydraziden der allgemeinen Formel (I) erhält man die nachfolgend genannten Verbindungen. In der nachfolgenden Tabelle 1 steht Y =„-" für eine direkte Bindung. Production Examples and taking into account the general information on the preparation of substituted Heteroarylcarbonsäurehydraziden of the general formula (I) gives the following compounds. In Table 1 below, Y = "-" represents a direct bond.
A1 . Verbindungen A1 -1 bis A1 -681 der allgemeinen Formel (Ia1 ), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen A1 -1 bis A1 -670) in der folgenden Tabelle 1 entsprechen. A1. Compounds A1 -1 to A1 -681 of the general formula (Ia1) in which R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 correspond to the definitions (Nos 1 to 681; 1 to A1 -670) in the following Table 1.
Tabelle 1 Table 1
No. R5 R6 Y A1 A2 A3 A4 A5 No. R 5 R 6 YA 1 A 2 A 3 A 4 A 5
1 H H - C-Cl C-H C-H C-H C-H1 H H - C-Cl C-H C-H C-H C-H
2 H H - C-H C-Cl C-H C-H C-H2 H H - C-H C-Cl C-H C-H C-H
3 H H - C-H C-H C-Cl C-H C-H3 H H -C-H C-H C-Cl C-H C-H
4 H H - C-Cl C-Cl C-H C-H C-H4 H H - C-Cl C-Cl C-H C-H C-H
5 H H - C-Cl C-H C-Cl C-H C-H5 H H - C-Cl C-H C-Cl C-H C-H
6 H H - C-Cl C-H C-H C-Cl C-H6 H H - C-Cl C-H C-H C-Cl C-H
7 H H - C-Cl C-H C-H C-H C-Cl7 H H - C-Cl C-H C-H C-H C-Cl
8 H H - C-H C-Cl C-Cl C-H C-H8 H H - C-H C-Cl C-Cl C-H C-H
9 H H - C-H C-Cl C-H C-Cl C-H9 H H - C-H C-Cl C-H C-Cl C-H
10 H H - C-Cl C-H C-Cl C-H C-Cl10 H H - C-Cl C-H C-Cl C-H C-Cl
1 1 H H - C-F C-H C-H C-H C-H 5 R6 Y A1 A2 A3 A4 A5 1 HH - CF CH CH CH CH 5 R 6 YA 1 A 2 A 3 A 4 A 5
H H - C-H C-F C-H C-H C-HH H -C-H C-F C-H C-H C-H
H H - C-H C-H C-F C-H C-HH H - C - H C - H C - F C - H C - H
H H - C-F C-F C-H C-H C-HH H - C-F C-F C-H C-H C-H
H H - C-F C-H C-F C-H C-HH H -C-F C-H C-F C-H C-H
H H - C-F C-H C-H C-F C-HH H -C-F C-H C-H C-F C-H
H H - C-F C-H C-H C-H C-FH H -C-F C-H C-H C-H C-F
H H - C-H C-F C-F C-H C-HH H - C - H C - F C - F C - H C - H
H H - C-H C-F C-H C-F C-HH H - C - H C - F C - H C - F C - H
H H - C-F C-H C-F C-H C-FH H -C-F C-H C-F C-H C-F
H H - N C-H C-H C-H C-HH H - N C - H C - H C - H C - H
H H - C-H N C-H C-H C-HH H - C - H N C - H C - H C - H
H H - C-H C-H N C-H C-HH H - C - H C - H N C - H C - H
H H - N N C-H C-H C-HH H - N N C - H C - H C - H
H H - N C-H N C-H C-HH H - N C - H N C - H C - H
H H - N C-H C-H N C-HH H - N C - H C - H N C - H
H H - N C-H C-H C-H NH H - N C - H C - H C - H N
H H - C-H N N C-H C-HH H - C - H N N C - H C - H
H H - C-H N C-H N C-HHH-C-HNC-HNC-H
H H - N C-OCHs C-H C-OCHs NH H - N C-OCHs C-H C-OCHs N
H H - N C-Cl C-H C-H C-HH H - N C-Cl C-H C-H C-H
H H - N C-H C-Cl C-H C-HH H - N C-H C-Cl C-H C-H
H H - N C-H C-H C-Cl C-HH H - N C - H C - H C - Cl C - H
H H - N C-H C-H C-H C-ClH H - N C - H C - H C - H C - Cl
H H - N C-H C-Cl C-H C-ClH H - N C-H C-Cl C-H C-Cl
H H - N C-H C-CF3 C-H C-ClHH-N CH C-CF 3 CH C-Cl
H H - N C-H C-CH3 C-OCHs C-CH3 HH-N CH C-CH 3 C-OCHs C-CH 3
H H - N C-H C-H C-H C-CH3 HH - N CH CH CH C-CH 3
H H - N C-H C-H C-CH3 C-HHH - N CH CHC CH 3 CH
H H - N C-H C-H C-Cl C-ClH H - N C - H C - H C - Cl C - Cl
H H - C-Br C-H C-H C-H C-HHH - C-Br C-H C-H C-H C-H
H H - C-H C-Br C-H C-H C-H 5 R6 Y A1 A2 A3 A4 A5 HH - CH C-Br CH CH CH 5 R 6 YA 1 A 2 A 3 A 4 A 5
H H - C-H C-H C-Br C-H C-HH H - C - H C - H C - Br C - H C - H
H H - C-F C-H C-Br C-H C-HH H -C-F C-H C-Br C-H C-H
H H - C-Cl C-H C-Br C-H C-HHH - C-Cl C-H C-Br C-H C-H
H H - C-Br C-H C-F C-H C-HHH - C-Br C-H C-F C-H C-H
H H - C-Br C-H C-Cl C-H C-HHH - C-Br C-H C-Cl C-H C-H
H H - C-H C-Cl C-Br C-H C-HH H -C-H C-Cl C-Br C-H C-H
H H - C-H C-Br C-Cl C-H C-HH H -C-H C-Br C-Cl C-H C-H
H H - C-H N C-H C-Br C-HH H -C-H N C-H C-Br C-H
H H - C-l C-H C-H C-H C-HH H - C-1 C-H C-H C-H C-H
H H - C-H C-l C-H C-H C-HH H -C-H C-1 C-H C-H C-H
H H - C-H C-H C-l C-H C-HH H -C-H C-H C-1 C-H C-H
H H - C-F C-H C-l C-H C-HH H -C-F C-H C-1 C-H C-H
H H - C-F C-H C-Cl C-H C-HH H -C-F C-H C-Cl C-H C-H
H H - C-F C-H C-H C-Cl C-HH H -C-F C-H C-H C-Cl C-H
H H - C-H C-F C-Cl C-H C-HH H - C - H C - F C - Cl C - H C - H
H H - C-H C-Cl C-F C-H C-HH H - C-H C-Cl C-F C-H C-H
H H - C-F C-H C-H C-H C-ClH H -C-F C-H C-H C-H C-Cl
H H - C-H C-F C-H C-Cl C-HH H - C-H C-F C-H C-Cl C-H
H H - C-CN C-H C-H C-H C-HH H - C-CN C-H C-H C-H C-H
H H - C-H C-CN C-H C-H C-HH H - C - H C - CN C - H C - H C - H
H H - C-H C-H C-CN C-H C-HH H -C-H C-H C-CN C-H C-H
H H - C-Cl C-H C-CN C-H C-HH H - C-Cl C-H C-CN C-H C-H
H H - C-H C-Cl C-H C-CN C-HH H -C-H C-Cl C-H C-CN C-H
H H - C-OEt C-H C-H C-H C-HH H - C-OEt C-H C-H C-H C-H
H H - C-H C-OEt C-H C-H C-HH H -C-H C-OEt C-H C-H C-H
H H - C-H C-H C-OEt C-H C-HHH-C-H C-H C-OEt C-H C-H
H H - C-Cl C-H C-OEt C-H C-HHH - C-Cl C-H C-OEt C-H C-H
H H - C-H C-Cl C-H C-OEt C-HHH - C-H C-Cl C-H C-OEt C-H
H H - C-CH3 C-H C-H C-H C-HHH - C - CH 3 CH CH CH CH
H H - C-H C-CH3 C-H C-H C-HH - CH C - CH 3 CH CH CH
H H - C-H C-H C-CH3 C-H C-H No. R5 R6 Y A1 A2 A3 A4 A5 H - CH CH C - CH 3 CH CH No. R 5 R 6 YA 1 A 2 A 3 A 4 A 5
74 H H - C-CHs C-CHs C-H C-H C-H74 H H - C-CHs C-CHs C-H C-H C-H
75 H H - C-CHs C-H C-CHs C-H C-H75 H H - C-CHs C-H C-CHs C-H C-H
76 H H - C-CHs C-H C-H C-CHs C-H76 H H - C-CHs C-H C-H C-CHs C-H
77 H H - C-CHs C-H C-H C-H C-CHs77 H H - C-CHs C-H C-H C-H C-CHs
78 H H - C-H C-CHs C-CHs C-H C-H78 H H - C-H C-CHs C-CHs C-H C-H
79 H H - C-H C-CHs C-H C-CHs C-H79 H H - C-H C-CHs C-H C-CHs C-H
80 H H - C-CHs C-H C-CHs C-H C-CHs80 H H - C-CHs C-H C-CHs C-H C-CHs
81 H H - C-CFs C-H C-H C-H C-H81 H H - C-CFs C-H C-H C-H C-H
82 H H - C-H C-CFs C-H C-H C-H82 H H - C-H C-CFs C-H C-H C-H
83 H H - C-H C-H C-CFs C-H C-H83 H H -C-H C-H C-CFs C-H C-H
84 H H - C-CFs C-Cl C-H C-H C-H84 H H - C-CFs C-Cl C-H C-H C-H
85 H H - C-CFs C-H C-CFs C-H C-H85 H H - C-CFs C-H C-CFs C-H C-H
86 H H - C-Cl C-H C-H C-CFs C-H86 H H - C-Cl C-H C-H C-CFs C-H
87 H H - C-Cl C-H C-H C-H C-CFs87 H H - C-Cl C-H C-H C-H C-CFs
88 H H - C-H C-CFs C-CFs C-H C-H88 H H -C-H C-CFs C-CFs C-H C-H
89 H H - C-H C-CFs C-H C-CFs C-H89 H H -C-H C-CFs C-H C-CFs C-H
90 H H - C-Cl C-H C-Cl C-H C-CFs90 H H - C-Cl C-H C-Cl C-H C-CFs
91 H H - C-Cl C-H C-CFs C-H C-H91 H H - C-Cl C-H C-CFs C-H C-H
92 H H - C-CFs C-H C-Cl C-H C-H92 H H - C-CFs C-H C-Cl C-H C-H
93 H H - C-H C-Cl C-CFs C-H C-H93 H H - C-H C-Cl C-CFs C-H C-H
94 H H - C-H N C-Cl C-H C-H94 H H - C-H N C-Cl C-H C-H
95 H H - C-H N C-F C-H C-H95 H H - C - H N C - F C - H C - H
96 H H - C-H N C-CFs C-H C-H96 H H - C-H N C-CFs C-H C-H
96 H H - C-H N C- H C-CFs C-H96 H H - C - H N C - H C - CFs C - H
97 H H - C-Cl N C-H C-H C-H97 H H - C-Cl N C-H C-H C-H
98 H H - C-H N C-H C-Cl C-H98 H H -C-H N C-H C-Cl C-H
99 H H - C-Cl N C-Cl C-H C-H99 H H - C-Cl N C-Cl C-H C-H
100 H H - C-Cl N C-H C-H C-Cl100 H H - C-Cl N C-H C-H C-Cl
101 H H - C-OCHs C-H C-H C-H C-H101 H H - C-OCHs C-H C-H C-H C-H
102 H H - C-H C-OCHs C-H C-H C-H102HH-C-H C-OCHs C-H C-H C-H
103 H H - C-H C-H C-OCHs C-H C-H No. R5 R6 Y A1 A2 A3 A4 A5 103 HH - CH CH C-OCHs CH CH No. R 5 R 6 YA 1 A 2 A 3 A 4 A 5
104 H H - C-OCHs C-OCHs C-H C-H C-H104 H H - C-OCHs C-OCHs C-H C-H C-H
105 H H - C-OCHs C-H C-OCHs C-H C-H105 H H - C-OCHs C-H C-OCHs C-H C-H
106 H H - C-OCHs C-H C-H C-OCHs C-H106 H H - C-OCHs C-H C-H C-OCHs C-H
107 H H - C-OCHs C-H C-H C-H C-Cl107 H H - C-OCHs C-H C-H C-H C-Cl
108 H H - C-H C-OCHs C-OCHs C-H C-H108 H H - C-H C-OCHs C-OCHs C-H C-H
109 H H - C-H C-OCHs C-H C-OCHs C-H109HH-C-H C-OCHs C-H C-OCHs C-H
1 10 H H - C-H C-OCHs C-OCHs C-OCHs C-H1 H-C-H C-OCHs C-OCHs C-OCHs C-H
101 H H - C-SCHs C-H C-H C-H C-H101 H H - C-SCHs C-H C-H C-H C-H
102 H H - C-H C-SCHs C-H C-H C-H102 H H - C - H C - SCHs C - H C - H C - H
103 H H - C-H C-H C-SCHs C-H C-H103 H H - C-H C-H C-SCHs C-H C-H
104 H H - C-SCFs C-H C-H C-H C-H104 H H - C-SCFs C-H C-H C-H C-H
105 H H - C-H C-SCFs C-H C-H C-H105 H H - C-H C-SCFs C-H C-H C-H
106 H H - C-H C-H C-SCFs C-H C-H106 H H-C-H C-H C-SCFs C-H C-H
107 H H - C-OCFs C-H C-H C-H C-H107 H H - C-OCFs C-H C-H C-H C-H
108 H H - C-H C-OCFs C-H C-H C-H108 H H - C-H C-OCFs C-H C-H C-H
109 H H - C-H C-H C-OCFs C-H C-H109 H H - C-H C-H C -OCFs C-H C-H
1 10 H H - C-NO2 C-H C-H C-H C-H1 HH - C-NO 2 CH CH CH CH
1 1 1 H H - C-H C-NO2 C-H C-H C-H1 1 1 H H-C-H C-NO 2 C-H C-H C-H
1 12 H H - C-H C-H C-NO2 C-H C-H1 12 H H - C-H C-H C-NO2 C-H C-H
1 13 H H - C-Cl C-H C-NO2 C-H C-H1 13 H H - C-Cl C-H C-NO2 C-H C-H
1 14 H H - C-Cl C-H C-OCHs C-H C-H1 14 H H - C-Cl C-H C-OCHs C-H C-H
1 15 H H - C-H C-Cl C-OCHs C-H C-H1 HH-C-H C-Cl C-OCHs C-H C-H
1 16 H H - C-SCN C-H C-H C-H C-H1 16 H H - C-SCN C-H C-H C-H C-H
1 17 H H - C-H C-SCN C-H C-H C-H1 17 H H - C-H C-SCN C-H C-H C-H
1 18 H H - C-H C-H C-SCN C-H C-H1 18 H H-C-H C-H C-SCN C-H C-H
1 19 H H - C-H N C-CHs C-H C-H1 19 H H - C-H N C-CHs C-H C-H
120 H H - C-H N C-OCH C-H C-H 120 H H -C-H N C-OCH C-H C-H
121 H H - N C-H C-H No. R5 R6 Y A1 A2 A3 A4 A5 121 HH - N CH CH No. R 5 R 6 YA 1 A 2 A 3 A 4 A 5
170 CH3 H - C-CN C-H C-H C-H C-H170 CH 3 H - C-CN CH CH CH CH
171 CHs H - C-H C-H C-l C-H C-H171 CHs H - C - H C - H C - I C - H C - H
172 CHs H - C-H C-H C-OCHs C-H C-H172 CHs H - C - H C - H C - OCHs C - H C - H
173 CHs H - C-H C-H C-CFs C-H C-H173 CHs H-C-H C-H C-CFs C-H C-H
174 CHs H - C-H C-H C-CHs C-H C-H174 CHs H - C - H C - H C - CHs C - H C - H
175 CHs H - C-H C-H C-CN C-H C-H175 CHs H - C - H C - H C - CN C - H C - H
176 CHs H - C-H C-H C-SCFs C-H C-H176 CHs H-C-H C-H C-SCFs C-H C-H
177 CHs H - C-H C-H C-OCFs C-H C-H177 CHs H-C-H C-H C-OCFs C-H C-H
178 CHs H - C-H C-H C-OEt C-H C-H178 CHs H - C - H C - H C - OEt C - H C - H
179 CHs H - C-H C-H C-t-Bu C-H C-H179 CHs H-C-H C-H C-t-Bu C-H C-H
180 CHs H - C-F C-H C-Br C-H C-H180 CHs H-C-F C-H C-Br C-H C-H
181 CHs H - N C-H C-H C-H C-H181 CHs H - N C - H C - H C - H C - H
182 CHs H - N C-Cl C-H C-H C-H182 CHs H - N C-Cl C-H C-H C-H
183 CHs H - N C-H C-Cl C-H C-H183 CHs H - N C - H C - Cl C - H C - H
184 CHs H - N C-H C-H C-H C-Cl184 CHs H - N C - H C - H C - H C - Cl
185 CHs H - C-H N C-H C-H C-H185 CHs H - C - H N C - H C - H C - H
186 CHs H - C-H N C-Cl C-H C-H186 CHs H - C - H N C - Cl C - H C - H
187 CHs H - C-H C-H N C-H C-H187 CHs H - C - H C - H N C - H C - H
188 CHs H - N C-H C-H C-H N188 CHs H - N C - H C - H C - H N
189 CHs H - N C-H C-H N C-H189 CHs H - N C - H C - H N C - H
190 CHs H - C-Cl C-H N C-H C-H190 CHs H - C - Cl C - H N C - H C - H
191 CHs H - C-H C-l C-H C-H C-H191 CHs H - C - H C - I C - H C - H C - H
192 CHs H - C-H C-OCHs C-H C-H C-H192 CHs H - C - H C - OCHs C - H C - H C - H
193 CHs H - C-H C-CFs C-H C-H C-H193 CHs H-C-H C-CFs C-H C-H C-H
194 CHs H - C-H C-CHs C-H C-H C-H194 CHs H - C - H C - CHs C - H C - H C - H
195 CHs H - C-H C-CN C-H C-H C-H195 CHs H - C - H C - CN C - H C - H C - H
196 CHs H - C-H C-CHs C-H C-H C-H196 CHs H-C-H C-CHs C-H C-H C-H
197 CHs H - C-H C-Cl C-H C-Cl C-H197 CHs H - C - H C - Cl C - H C - Cl C - H
198 CHs H - C-H C-SCFs C-H C-H C-H198 CHs H-C-H C-SCFs C-H C-H C-H
199 CHs H - C-H C-OCFs C-H C-H C-H199 CHs H-C-H C-OCFs C-H C-H C-H
200 CHs H - C-H C-OEt C-H C-H C-H No. R5 R6 Y A1 A2 A3 A4 A5 200 CHs H - CH C-OEt CH CH CH No. R 5 R 6 YA 1 A 2 A 3 A 4 A 5
201 Et H - C-H C-H C-H C-H C-H201 EtH - C-H C-H C-H C-H C-H
202 Et H - C-Cl C-H C-H C-H C-H202 EtH - C-Cl C-H C-H C-H C-H
203 Et H - C-H C-Cl C-H C-H C-H203 Et H - C-H C-Cl C-H C-H C-H
204 Et H - C-H C-H C-Cl C-H C-H204 Et H-C-H C-H C-Cl C-H C-H
205 Et H - C-Cl C-H C-Cl C-H C-H205 Et H - C-Cl C-H C-Cl C-H C-H
206 Et H - C-Cl C-H C-H C-Cl C-H206 Et H - C-Cl C-H C-H C-Cl C-H
207 Et H - C-F C-H C-H C-H C-H207 EtH - C-F C-H C-H C-H C-H
208 Et H - C-H C-F C-H C-H C-H208 Et H-C-H C-F C-H C-H C-H
209 Et H - C-H C-H C-F C-H C-H209 EtH - C-H C-H C-F C-H C-H
210 Et H - C-F C-H C-F C-H C-H210 Et H - C-F C-H C-F C-H C-H
21 1 Et H - C-H C-F C-H C-F C-H21 1 EtH-C-H C-F C-H C-F C-H
212 Et H - C-F C-H C-H C-H C-F212 Et H-C-F C-H C-H C-H C-F
213 Et H - C-Br C-H C-H C-H C-H213 Et H - C-Br C-H C-H C-H C-H
214 Et H - C-H C-Br C-H C-H C-H214 EtH - C-H C-Br C-H C-H C-H
215 Et H - C-H C-H C-Br C-H C-H215 Et H - C-H C-H C-Br C-H C-H
216 Et H - C-l C-H C-H C-H C-H216 Et H-C-1 C-H C-H C-H C-H
217 Et H - C-OCHs C-H C-H C-H C-H217 Et H - C-OCHs C-H C-H C-H C-H
218 Et H - C-CF3 C-H C-H C-H C-H218 Et H - C-CF 3 CH CH CH CH
219 Et H - C-CH3 C-H C-H C-H C-H219 Et H - C-CH 3 CH CH CH CH
220 Et H - C-CN C-H C-H C-H C-H220 EtH - C-CN C-H C-H C-H C-H
221 Et H - C-H C-H C-l C-H C-H221 EtH - C-H C-H C-1 C-H C-H
222 Et H - C-H C-H C-OCHs C-H C-H222 EtH-C-H C-H C-OCHs C-H C-H
223 Et H - C-H C-H C-CF3 C-H C-H223 Et H - CH CH C-CF 3 CH CH
224 Et H - C-H C-H C-CH3 C-H C-H224 Et H - CH CH C - CH 3 CH CH
225 Et H - C-H C-H C-CN C-H C-H225 Et H-C-H C-H C-CN C-H C-H
226 Et H - C-H C-H C-SCFs C-H C-H226 EtH - C-H C-H C-SCFs C-H C-H
227 Et H - C-H C-H C-OCFs C-H C-H227 Et H-C-H C-H C-OCFs C-H C-H
228 Et H - C-H C-H C-OEt C-H C-H228 EtH - C-H C-H C-OEt C-H C-H
229 Et H - C-H C-H C-t-Bu C-H C-H229 EtH - C-H C-H C-t-Bu C-H C-H
230 Et H - C-F C-H C-Br C-H C-H230 Et H - C-F C-H C-Br C-H C-H
231 Et H - N C-H C-H C-H C-H No. R5 R6 Y A1 A2 A3 A4 A5 231 Et H - N CH CH CH CH No. R 5 R 6 YA 1 A 2 A 3 A 4 A 5
232 Et H - N C-Cl C-H C-H C-H232 Et H - N C-Cl C-H C-H C-H
233 Et H - N C-H C-Cl C-H C-H233 EtH - N C-H C-Cl C-H C-H
234 Et H - N C-H C-H C-H C-Cl234 Et H - N C-H C-H C-H C-Cl
235 Et H - C-H N C-H C-H C-H235 Et H - C-H N C-H C-H C-H
236 Et H - C-H N C-Cl C-H C-H236 Et H - C-H N C-Cl C-H C-H
237 Et H - C-H C-H N C-H C-H237 Et H - C-H C-H N C-H C-H
238 Et H - N C-H C-H C-H N238 Et H - N C-H C-H C-H N
239 Et H - N C-H C-H N C-H239 Et H - N C-H C-H N C-H
240 Et H - C-Cl C-H N C-H C-H240 Et H - C-Cl C-H N C-H C-H
241 Et H - C-H C-l C-H C-H C-H241 EtH - C-H C-1 C-H C-H C-H
242 Et H - C-H C-OCHs C-H C-H C-H242 EtH - C-H C-OCHs C-H C-H C-H
243 Et H - C-H C-CF3 C-H C-H C-H243 Et H - CH C-CF 3 CH CH CH
244 Et H - C-H C-CH3 C-H C-H C-H244 Et H - CH C-CH 3 CH CH CH
245 Et H - C-H C-CN C-H C-H C-H245 EtH - C-H C-CN C-H C-H C-H
246 Et H - C-H C-CH3 C-H C-H C-H246 Et H - CH C-CH 3 CH CH CH
247 Et H - C-H C-Cl C-H C-Cl C-H247 EtH - C-H C-Cl C-H C-Cl C-H
248 Et H - C-H C-SCFs C-H C-H C-H248 EtH - C-H C-SCFs C-H C-H C-H
249 Et H - C-H C-OCFs C-H C-H C-H249 EtH - C-H C-OCFs C-H C-H C-H
250 Et H - C-H C-OEt C-H C-H C-H250 Et H - C-H C-OEt C-H C-H C-H
251 i-Pr H - C-H C-H C-H C-H C-H251 i-Pr H - C-H C-H C-H C-H C-H
252 i-Pr H - C-Cl C-H C-H C-H C-H252 i-Pr H - C-Cl C-H C-H C-H C-H
253 i-Pr H - C-H C-Cl C-H C-H C-H253 i-Pr H - C-H C-Cl C-H C-H C-H
254 i-Pr H - C-H C-H C-Cl C-H C-H254 i-Pr H - C-H C-H C-Cl C-H C-H
255 i-Pr H - C-Cl C-H C-Cl C-H C-H255 i-Pr H - C-Cl C-H C-Cl C-H C-H
256 i-Pr H - C-Cl C-H C-H C-Cl C-H256 i-Pr H - C-Cl C-H C-H C-Cl C-H
257 i-Pr H - C-F C-H C-H C-H C-H257 i-Pr H - C-F C-H C-H C-H C-H
258 i-Pr H - C-H C-F C-H C-H C-H258 i-Pr H - C-H C-F C-H C-H C-H
259 i-Pr H - C-H C-H C-F C-H C-H259 i-Pr H - C-H C-H C-F C-H C-H
260 i-Pr H - C-F C-H C-F C-H C-H260 i-Pr H-C-F C-H C-F C-H C-H
261 i-Pr H - C-H C-F C-H C-F C-H261 i-Pr H - C-H C-F C-H C-F C-H
262 i-Pr H - C-F C-H C-H C-H C-F No. R5 R6 Y A1 A2 A3 A4 A5 262 i-Pr H - CF CH CH CH CF No. R 5 R 6 YA 1 A 2 A 3 A 4 A 5
263 i-Pr H - C-Br C-H C-H C-H C-H263 i-Pr H - C-Br C-H C-H C-H C-H
264 i-Pr H - C-H C-Br C-H C-H C-H264 i-Pr H - C-H C-Br C-H C-H C-H
265 i-Pr H - C-H C-H C-Br C-H C-H265 i-Pr H - C-H C-H C-Br C-H C-H
266 i-Pr H - C-l C-H C-H C-H C-H266 i-Pr H - C-1 C-H C-H C-H C-H
267 i-Pr H - C-OCHs C-H C-H C-H C-H267 i-Pr H - C-OCHs C-H C-H C-H C-H
268 i-Pr H - C-CF3 C-H C-H C-H C-H268 i-Pr H - C-CF 3 CH CH CH CH
269 i-Pr H - C-CHs C-H C-H C-H C-H269 i-Pr H - C-CHs C-H C-H C-H C-H
270 i-Pr H - C-CN C-H C-H C-H C-H270 i-Pr H - C-CN C-H C-H C-H C-H
271 i-Pr H - C-H C-H C-l C-H C-H271 i-Pr H - C-H C-H C-1 C-H C-H
272 i-Pr H - C-H C-H C-OCHs C-H C-H272 i-Pr H - C-H C-H C-OCHs C-H C-H
273 i-Pr H - C-H C-H C-CF3 C-H C-H273 i-Pr H - CH CH C-CF 3 CH CH
274 i-Pr H - C-H C-H C-CH3 C-H C-H274 i-Pr H - CH CH C -CH 3 CH CH
275 i-Pr H - C-H C-H C-CN C-H C-H275 i-Pr H - C-H C-H C-CN C-H C-H
276 i-Pr H - C-H C-H C-SCFs C-H C-H276 i-Pr H - C-H C-H C-SCFs C-H C-H
277 i-Pr H - C-H C-H C-OCFs C-H C-H277 i-Pr H-C-H C-H C-OCFs C-H C-H
278 i-Pr H - C-H C-H C-OEt C-H C-H278 i-Pr H - C-H C-H C-OEt C-H C-H
279 i-Pr H - C-H C-H C-t-Bu C-H C-H279 i-Pr H - C-H C-H C-t-Bu C-H C-H
280 i-Pr H - C-F C-H C-Br C-H C-H280 i-Pr H - C-F C-H C-Br C-H C-H
281 i-Pr H - N C-H C-H C-H C-H281 i-Pr H - N C-H C-H C-H C-H
282 i-Pr H - N C-Cl C-H C-H C-H282 i-Pr H - N C-Cl C-H C-H C-H
283 i-Pr H - N C-H C-Cl C-H C-H283 i-Pr H - N C-H C-Cl C-H C-H
284 i-Pr H - N C-H C-H C-H C-Cl284 i-Pr H - N C-H C-H C-H C-Cl
285 i-Pr H - C-H N C-H C-H C-H285 i-Pr H - C-H N C-H C-H C-H
286 i-Pr H - C-H N C-Cl C-H C-H286 i-Pr H - C-H N C-Cl C-H C-H
287 i-Pr H - C-H C-H N C-H C-H287 i-Pr H - C-H C-H N C-H C-H
288 i-Pr H - N C-H C-H C-H N288 i-Pr H - N C-H C-H C-H N
289 i-Pr H - N C-H C-H N C-H289 i-Pr H - N C-H C-H N C-H
290 i-Pr H - C-Cl C-H N C-H C-H290 i-Pr H - C-Cl C-H N C-H C-H
291 i-Pr H - C-H C-l C-H C-H C-H291 i-Pr H - C-H C-1 C-H C-H C-H
292 i-Pr H - C-H C-OCHs C-H C-H C-H292 i-Pr H - C-H C-OCHs C-H C-H C-H
293 i-Pr H - C-H C-CF3 C-H C-H C-H R5 R6 Y A1 A2 A3 A4 A5 i-Pr H - C-H C-CH3 C-H C-H C-H i-Pr H - C-H C-CN C-H C-H C-H i-Pr H - C-H C-CH3 C-H C-H C-H i-Pr H - C-H C-Cl C-H C-Cl C-H i-Pr H - C-H C-SCF3 C-H C-H C-H i-Pr H - C-H C-OCF3 C-H C-H C-H i-Pr H - C-H C-OEt C-H C-H C-H c-Pr H - C-H C-H C-H C-H C-H c-Pr H - C-Cl C-H C-H C-H C-H c-Pr H - C-H C-Cl C-H C-H C-H c-Pr H - C-H C-H C-Cl C-H C-H c-Pr H - C-Cl C-H C-Cl C-H C-H c-Pr H - C-Cl C-H C-H C-Cl C-H c-Pr H - C-F C-H C-H C-H C-H c-Pr H - C-H C-F C-H C-H C-H c-Pr H - C-H C-H C-F C-H C-H c-Pr H - C-F C-H C-F C-H C-H c-Pr H - C-H C-F C-H C-F C-H c-Pr H - C-F C-H C-H C-H C-F c-Pr H - C-Br C-H C-H C-H C-H c-Pr H - C-H C-Br C-H C-H C-H c-Pr H - C-H C-H C-Br C-H C-H c-Pr H - C-l C-H C-H C-H C-H c-Pr H - C-OCHs C-H C-H C-H C-H c-Pr H - C-CF3 C-H C-H C-H C-H c-Pr H - C-CH3 C-H C-H C-H C-H c-Pr H - C-CN C-H C-H C-H C-H c-Pr H - C-H C-H C-l C-H C-H c-Pr H - C-H C-H C-OCH3 C-H C-H c-Pr H - C-H C-H C-CF3 C-H C-H c-Pr H - C-H C-H C-CH3 C-H C-H R5 R6 Y A1 A2 A3 A4 A5 c-Pr H - C-H C-H C-CN C-H C-H c-Pr H - C-H C-H C-SCFs C-H C-H c-Pr H - C-H C-H C-OCFs C-H C-H c-Pr H - C-H C-H C-OEt C-H C-H c-Pr H - C-H C-H C-t-Bu C-H C-H c-Pr H - C-F C-H C-Br C-H C-H c-Pr H - N C-H C-H C-H C-H c-Pr H - N C-Cl C-H C-H C-H c-Pr H - N C-H C-Cl C-H C-H c-Pr H - N C-H C-H C-H C-Cl c-Pr H - C-H N C-H C-H C-H c-Pr H - C-H N C-Cl C-H C-H c-Pr H - C-H C-H N C-H C-H c-Pr H - N C-H C-H C-H N c-Pr H - N C-H C-H N C-H c-Pr H - C-Cl C-H N C-H C-H c-Pr H - C-H C-l C-H C-H C-H c-Pr H - C-H C-OCHs C-H C-H C-H c-Pr H - C-H C-CF3 C-H C-H C-H c-Pr H - C-H C-CH3 C-H C-H C-H c-Pr H - C-H C-CN C-H C-H C-H c-Pr H - C-H C-CH3 C-H C-H C-H c-Pr H - C-H C-Cl C-H C-Cl C-H c-Pr H - C-H C-SCFs C-H C-H C-H c-Pr H - C-H C-OCFs C-H C-H C-H c-Pr H - C-H C-OEt C-H C-H C-H293 i-Pr H - CH C-CF 3 CH CH CH R 5 R 6 YA 1 A 2 A 3 A 4 A 5 i-Pr H - CH C - CH 3 CH CH CH i - Pr H - CH C - CN CH CH CH i - Pr H - CH C - CH 3 CH CH CH i-Pr H - CH C-Cl CH C-Cl CH i-Pr H - CH C-SCF 3 CH CH CH i-Pr H - CH C -OCF 3 CH CH CH i-Pr H - CH C- OEt CH CH CH c-Pr H - CH CH CH CH CH c-Pr H - C-Cl CH CH CH CH c-Pr H - CH C-Cl CH CH CH c-Pr H - CH CH C-Cl CH CH c-Pr H - C-Cl CH C-Cl CH CH c-Pr H - C-Cl CH CH C-Cl CH c-Pr H - CF CH CH CH CH c-Pr H - CH CF CH CH CH c- Pr H - CH CH CF CH CH c Pr H - CF CH CF CH CH c Pr H - CH CF CH CF CH c Pr H - CF CH CH CH CF c Pr H - C - Br CH CH CH CH c-Pr H - CH C-Br CH CH CH c-Pr H - CH CH C-Br CH CH c-Pr H - Cl CH CH CH CH c-Pr H - C-OCHs CH CH CH CH c-Pr H - C-CF 3 CH CH CH CH c-Pr H - C-CH 3 CH CH CH CH c-Pr H - C-CN CH CH CH CH c-Pr H - CH CH Cl CH CH c-Pr H - CH CH C-OCH 3 CH CH c-Pr H - CH CH C-CF 3 CH CH c-Pr H - CH CH C-CH 3 CH CH R 5 R 6 YA 1 A 2 A 3 A 4 A 5 c-Pr H - CH CH C-CN CH CH c-Pr H - CH CH C-SCFs CH CH c-Pr H - CH CH C -OCFs CH CH c-Pr H - CH CH C-OEt CH CH c-Pr H - CH CH Ct-Bu CH CH c-Pr H - CF CH C-Br CH CH c-Pr H - N CH CH CH CH c-Pr H - N C - Cl CH CH CH c - Pr H - N CH C - Cl CH CH c - Pr H - N CH CH CH C - Cl c - Pr H - CH N CH CH CH c - Pr H - CH N C -Cl CH CH c-Pr H -CH CH N CH CH c-Pr H -N CH CH CH N c-Pr H -N CH CH N CH c-Pr H -C-Cl CH N CH CH c Pr H - CH Cl CH CH CH c-Pr H - CH C-OCHs CH CH CH c-Pr H - CH C-CF 3 CH CH CH c-Pr H - CH C-CH 3 CH CH CH c-Pr H - CH C-CN CH CH CH c-Pr H - CH C-CH 3 CH CH CH c-Pr H - CH C-Cl CH C-Cl CH c-Pr H - CH C-SCFs CH CH CH c-Pr H - CH C-OCFs CH CH CH c-Pr H - CH C-OEt CH CH CH
CH3 H CH2 C-H C-H C-H C-H C-HCH 3 H CH 2 CH CH CH CH CH
CH3 H CH2 C-Cl C-H C-H C-H C-HCH 3 H CH 2 C-Cl CH CH CH CH
CH3 H CH2 C-H C-Cl C-H C-H C-HCH 3 H CH 2 CH C-Cl CH CH CH
CH3 H CH2 C-H C-H C-Cl C-H C-HCH 3 H CH 2 CH CH C-Cl CH CH
CH3 H CH2 C-Cl C-H C-Cl C-H C-H R5 R6 Y A1 A2 A3 A4 A5 CH 3 H CH 2 C-Cl CH C-Cl CH CH R 5 R 6 YA 1 A 2 A 3 A 4 A 5
CH3 H CH2 C-Cl C-H C-H C-Cl C-HCH 3 H CH 2 C-Cl CH CH C-Cl CH
CH3 H CH2 C-F C-H C-H C-H C-HCH 3 H CH 2 CF CH CH CH CH
CH3 H CH2 C-H C-F C-H C-H C-HCH 3 H CH 2 CH CF CH CH CH
CH3 H CH2 C-H C-H C-F C-H C-HCH 3 H CH 2 CH CH CF CH CH
CH3 H CH2 C-F C-H C-F C-H C-HCH 3 H CH 2 CF CH CF CH CH
CH3 H CH2 C-H C-F C-H C-F C-HCH 3 H CH 2 CH CF CH CF CH
CH3 H CH2 C-F C-H C-H C-H C-FCH 3 H CH 2 CF CH CH CH CF
CH3 H CH2 C-Br C-H C-H C-H C-HCH 3 H CH 2 C-Br CH CH CH CH
CH3 H CH2 C-H C-Br C-H C-H C-HCH 3 H CH 2 CH C-Br CH CH CH
CH3 H CH2 C-H C-H C-Br C-H C-HCH 3 H CH 2 CH CH C-Br CH CH
CH3 H CH2 C-l C-H C-H C-H C-HCH 3 H CH 2 Cl CH CH CH CH
CH3 H CH2 C-OCHs C-H C-H C-H C-HCH 3 H CH 2 C-OCHs CH CH CH CH
CH3 H CH2 C-CF3 C-H C-H C-H C-HCH 3 H CH 2 C-CF 3 CH CH CH CH
CH3 H CH2 C-CH3 C-H C-H C-H C-HCH 3 H CH 2 C-CH 3 CH CH CH CH
CH3 H CH2 C-CN C-H C-H C-H C-HCH 3 H CH 2 C-CN CH CH CH CH
CH3 H CH2 C-H C-H C-l C-H C-HCH 3 H CH 2 CH CH Cl CH CH
CH3 H CH2 C-H C-H C-OCHs C-H C-HCH 3 H CH 2 CH CH C-OCHs CH CH
CH3 H CH2 C-H C-H C-CF3 C-H C-HCH 3 H CH 2 CH CH C-CF 3 CH CH
CH3 H CH2 C-H C-H C-CH3 C-H C-HCH 3 H CH 2 CH CH C-CH 3 CH CH
CH3 H CH2 C-H C-H C-CN C-H C-HCH 3 H CH 2 CH CH C-CN CH CH
CH3 H CH2 C-H C-H C-SCFs C-H C-HCH 3 H CH 2 CH CH C-SCF CH CH
CH3 H CH2 C-H C-H C-OCFs C-H C-HCH 3 H CH 2 CH CH C OCFs CH CH
CH3 H CH2 C-H C-H C-OEt C-H C-HCH 3 H CH 2 CH CH C-OEt CH CH
CH3 H CH2 C-H C-H C-t-Bu C-H C-HCH 3 H CH 2 CH CH Ct-Bu CH CH
CH3 H CH2 C-F C-H C-Br C-H C-HCH 3 H CH 2 CF CH C-Br CH CH
CH3 H CH2 N C-H C-H C-H C-HCH 3 H CH 2 N CH CH CH CH
CH3 H CH2 N C-Cl C-H C-H C-HCH 3 H CH 2 N C-Cl CH CH CH
CH3 H CH2 N C-H C-Cl C-H C-HCH 3 H CH 2 N CH C-Cl CH CH
CH3 H CH2 N C-H C-H C-H C-ClCH 3 H CH 2 N CH CH CH C-Cl
CH3 H CH2 C-H N C-H C-H C-HCH 3 H CH 2 CH N CH CH CH
CH3 H CH2 C-H N C-Cl C-H C-H R5 R6 Y A1 A2 A3 A4 A5 CH 3 H CH 2 CH N C-Cl CH CH R 5 R 6 YA 1 A 2 A 3 A 4 A 5
CH3 H CH2 C-H C-H N C-H C-HCH 3 H CH 2 CH CH N CH CH
CHs H CH2 N C-H C-H C-H NCHs H CH 2 N CH CH CH N
CHs H CH2 N C-H C-H N C-HCHs H CH 2 N CH CH N CH
CHs H CH2 C-Cl C-H N C-H C-HCHs H CH 2 C-Cl CH N CH CH
CHs H CH2 C-H C-l C-H C-H C-HCHs H CH 2 CH Cl CH CH CH
CHs H CH2 C-H C-OCHs C-H C-H C-HCHs H CH 2 CH C-OCHs CH CH CH
CHs H CH2 C-H C-CFs C-H C-H C-HCHs H CH 2 CH C-CFs CH CH CH
CHs H CH2 C-H C-CN C-H C-H C-HCHs H CH 2 CH C-CN CH CH CH
CHs H CH2 C-CHs C-H C-H C-H C-CHsCHs H CH 2 C-CHs CH CH CH C-CHs
CHs H CH2 C-Cl C-H C-H C-H C-ClCHs H CH 2 C-Cl CH CH CH C-Cl
CHs H CH2 C-H C-Cl C-H C-Cl C-HCHs H CH 2 CH C-Cl CH C-Cl CH
CHs H CH2 C-H C-SCFs C-H C-H C-HCHs H CH 2 CH C-SCFs CH CH CH
CHs H CH2 C-H C-OCFs C-H C-H C-HCHs H CH 2 CH C-OCFs CH CH CH
CHs H CH2 C-H C-OEt C-H C-H C-HCHs H CH 2 CH C-OEt CH CH CH
CHs H CH2CH2 C-H C-H C-H C-H C-HCHs H CH 2 CH 2 CH CH CH CH CH
CHs H CH2CH2 C-Cl C-H C-H C-H C-HCHs H CH 2 CH 2 C-Cl CH CH CH CH
CHs H CH2CH2 C-H C-Cl C-H C-H C-HCHs H CH 2 CH 2 CH C-Cl CH CH CH
CHs H CH2CH2 C-H C-H C-Cl C-H C-HCHs H CH 2 CH 2 CH CH C-Cl CH CH
CHs H CH2CH2 C-Cl C-H C-Cl C-H C-HCHs H CH 2 CH 2 C-Cl CH C-Cl CH CH
CHs H CH2CH2 C-Cl C-H C-H C-Cl C-HCHs H CH 2 CH 2 C-Cl CH CH C-Cl CH
CHs H CH2CH2 C-F C-H C-H C-H C-HCHs H CH 2 CH 2 CF CH CH CH CH
CHs H CH2CH2 C-H C-F C-H C-H C-HCHs H CH 2 CH 2 CH CF CH CH CH
CHs H CH2CH2 C-H C-H C-F C-H C-HCHs H CH 2 CH 2 CH CH CF CH CH
CHs H CH2CH2 C-F C-H C-F C-H C-HCHs H CH 2 CH 2 CF CH CF CH CH
CHs H CH2CH2 C-H C-F C-H C-F C-HCHs H CH 2 CH 2 CH CF CH CF CH
CHs H CH2CH2 C-F C-H C-H C-H C-FCHs H CH 2 CH 2 CF CH CH CH CF
CHs H CH2CH2 C-Br C-H C-H C-H C-HCHs H CH 2 CH 2 C-Br CH CH CH CH
CHs H CH2CH2 C-H C-Br C-H C-H C-HCHs H CH 2 CH 2 CH C-Br CH CH CH
CHs H CH2CH2 C-H C-H C-Br C-H C-HCHs H CH 2 CH 2 CH CH C-Br CH CH
CHs H CH2CH2 C-l C-H C-H C-H C-HCHs H CH 2 CH 2 Cl CH CH CH CH
CHs H CH2CH2 C-OCHs C-H C-H C-H C-H R5 R6 Y A1 A2 A3 A4 A5 CHs H CH 2 CH 2 C-OCHs CH CH CH CH R 5 R 6 YA 1 A 2 A 3 A 4 A 5
CH3 H CH2CH2 C-CFs C-H C-H C-H C-HCH 3 H CH 2 CH 2 C-CFs CH CH CH CH
CHs H CH2CH2 C-CHs C-H C-H C-H C-HCHs H CH2CH2 C-CHs C-H C-H C-H C-H
CHs H CH2CH2 C-CN C-H C-H C-H C-HCHs H CH2CH2 C-CN C-H C-H C-H C-H
CHs H CH2CH2 C-H C-H C-l C-H C-HCHs H CH2CH2 C-H C-H C-1 C-H C-H
CHs H CH2CH2 C-H C-H C-OCHs C-H C-HCHs H CH2CH2 C-H C-H C-OCHs C-H C-H
CHs H CH2CH2 C-H C-H C-CFs C-H C-HCHs H CH2CH2 C-H C-H C-CFs C-H C-H
CHs H CH2CH2 C-H C-H C-CHs C-H C-HCHs H CH2CH2 C-H C-H C-CHs C-H C-H
CHs H CH2CH2 C-H C-H C-CN C-H C-HCHs H CH2CH2 C-H C-H C-CN C-H C-H
CHs H CH2CH2 C-H C-H C-SCFs C-H C-HCHs H CH2CH2 C-H C-H C-SCFs C-H C-H
CHs H CH2CH2 C-H C-H C-OCFs C-H C-HCHs H CH2CH2 C-H C-H C-OCFs C-H C-H
CHs H CH2CH2 C-H C-H C-OEt C-H C-HCHs H CH2CH2 C-H C-H C-OEt C-H C-H
CHs H CH2CH2 C-H C-H C-t-Bu C-H C-HCHs H CH2CH2 C-H C-H C-t-Bu C-H C-H
CHs H CH2CH2 C-F C-H C-Br C-H C-HCHs H CH2CH2 C-F C-H C-Br C-H C-H
CHs H CH2CH2 N C-H C-H C-H C-HCHs H CH2CH2 N C-H C-H C-H C-H
CHs H CH2CH2 N C-Cl C-H C-H C-HCHs H CH2CH2 N C-Cl C-H C-H C-H
CHs H CH2CH2 N C-H C-Cl C-H C-HCHs H CH2CH2 N C-H C-Cl C-H C-H
CHs H CH2CH2 N C-H C-H C-H C-ClCHs H CH2CH2 N C-H C-H C-H C-Cl
CHs H CH2CH2 C-H N C-H C-H C-HCHs H CH2CH2 C-H N C-H C-H C-H
CHs H CH2CH2 C-H N C-Cl C-H C-HCHs H CH2CH2 C-H N C-Cl C-H C-H
CHs H CH2CH2 C-H C-H N C-H C-HCHs H CH2CH2 C-H C-H N C-H C-H
CHs H CH2CH2 N C-H C-H C-H NCHs H CH2CH2 N C-H C-H C-H N
CHs H CH2CH2 N C-H C-H N C-HCHs H CH2CH2 N C-H C-H N C-H
CHs H CH2CH2 C-Cl C-H N C-H C-HCHs H CH2CH2 C-Cl C-H N C-H C-H
CHs H CH2CH2 C-H C-l C-H C-H C-HCHs H CH2CH2 C-H C-1 C-H C-H C-H
CHs H CH2CH2 C-H C-OCHs C-H C-H C-HCHs H CH2CH2 C-H C-OCHs C-H C-H C-H
CHs H CH2CH2 C-H C-CFs C-H C-H C-HCHs H CH2CH2 C-H C-CFs C-H C-H C-H
CHs H CH2CH2 C-H C-CN C-H C-H C-HCHs H CH2CH2 C-H C-CN C-H C-H C-H
CHs H CH2CH2 C-CHs C-H C-H C-H C-CHsCHs H CH2CH2 C-CHs C-H C-H C-H C-CHs
CHs H CH2CH2 C-Cl C-H C-H C-H C-ClCHs H CH2CH2 C-Cl C-H C-H C-H C-Cl
CHs H CH2CH2 C-H C-Cl C-H C-Cl C-HCHs H CH2CH2 C-H C-Cl C-H C-Cl C-H
CHs H CH2CH2 C-H C-SCFs C-H C-H C-H R5 R6 Y A1 A2 A3 A4 A5 CHs H CH2 CH2 CH C-SCFs CH CH CH R 5 R 6 YA 1 A 2 A 3 A 4 A 5
CH3 H CH2CH2 C-H C-OCFs C-H C-H C-HCH 3 H CH 2 CH 2 CH C OCFs CH CH CH
CHs H CH2CH2 C-H C-OEt C-H C-H C-HCHs H CH2CH2 C-H C-OEt C-H C-H C-H
H H CH2CH2 C-H C-H C-H C-H C-HHH CH2CH2 C-H C-H C-H C-H C-H
H H CH2CH2 C-Cl C-H C-H C-H C-HHH CH2CH2 C-Cl C-H C-H C-H C-H
H H CH2CH2 C-H C-Cl C-H C-H C-HH H CH 2 CH 2 C-H C-Cl C-H C-H C-H
H H CH2CH2 C-H C-H C-Cl C-H C-HHH CH2CH2 C-H C-H C-Cl C-H C-H
H H CH2CH2 C-Cl C-H C-Cl C-H C-HH H CH 2 CH 2 C-Cl C-H C-Cl C-H C-H
H H CH2CH2 C-Cl C-H C-H C-Cl C-HH H CH 2 CH 2 C-Cl C-H C-H C-Cl C-H
H H CH2CH2 C-F C-H C-H C-H C-HHH CH2CH2 C-F C-H C-H C-H C-H
H H CH2CH2 C-H C-F C-H C-H C-HHH CH2CH2 C-H C-F C-H C-H C-H
H H CH2CH2 C-H C-H C-F C-H C-HHH CH2CH2 C-H C-H C-F C-H C-H
H H CH2CH2 C-F C-H C-F C-H C-HHH CH2CH2 C-F C-H C-F C-H C-H
H H CH2CH2 C-H C-F C-H C-F C-HHH CH2CH2 C-H C-F C-H C-F C-H
H H CH2CH2 C-F C-H C-H C-H C-FHH CH2CH2 C-F C-H C-H C-H C-F
H H CH2CH2 C-Br C-H C-H C-H C-HHH CH2CH2 C-Br C-H C-H C-H C-H
H H CH2CH2 C-H C-Br C-H C-H C-HHH CH2CH2 C-H C-Br C-H C-H C-H
H H CH2CH2 C-H C-H C-Br C-H C-HHH CH2CH2 C-H C-H C-Br C-H C-H
H H CH2CH2 C-l C-H C-H C-H C-HH H CH 2 CH 2 C-1 C-H C-H C-H C-H
H H CH2CH2 C-OCHs C-H C-H C-H C-HHH CH2CH2 C-OCHs C-H C-H C-H C-H
H H CH2CH2 C-CFs C-H C-H C-H C-HHH CH2CH2 C-CFs C-H C-H C-H C-H
H H CH2CH2 C-CHs C-H C-H C-H C-HH H CH 2 CH 2 C-CHs C-H C-H C-H C-H
H H CH2CH2 C-CN C-H C-H C-H C-HHH CH2CH2 C-CN C-H C-H C-H C-H
H H CH2CH2 C-H C-H C-l C-H C-HHH CH2CH2 C-H C-H C-1 C-H C-H
H H CH2CH2 C-H C-H C-OCHs C-H C-HHH CH2CH2 C-H C-H C-OCHs C-H C-H
H H CH2CH2 C-H C-H C-CFs C-H C-HHH CH2CH2 C-H C-H C-CFs C-H C-H
H H CH2CH2 C-H C-H C-CHs C-H C-HHH CH2CH2 C-H C-H C-CHs C-H C-H
H H CH2CH2 C-H C-H C-CN C-H C-HHH CH2CH2 C-H C-H C-CN C-H C-H
H H CH2CH2 C-H C-H C-SCFs C-H C-HHH CH2CH2 C-H C-H C-SCFs C-H C-H
H H CH2CH2 C-H C-H C-OCFs C-H C-HHH CH2CH2 C-H C-H C-OCFs C-H C-H
H H CH2CH2 C-H C-H C-OEt C-H C-HHH CH2CH2 C-H C-H C-OEt C-H C-H
H H CH2CH2 C-H C-H C-t-Bu C-H C-H 5 R6 Y A1 A2 A3 A4 A5 HH CH 2 CH 2 CH CH Ct-Bu CH CH 5 R 6 YA 1 A 2 A 3 A 4 A 5
H H CH2CH2 C-F C-H C-Br C-H C-HHH CH2CH2 C-F C-H C-Br C-H C-H
H H CH2CH2 N C-H C-H C-H C-HHH CH2CH2 N C-H C-H C-H C-H
H H CH2CH2 N C-Cl C-H C-H C-HH H CH 2 CH 2 N C-Cl C-H C-H C-H
H H CH2CH2 N C-H C-Cl C-H C-HH H CH 2 CH 2 N C-H C-Cl C-H C-H
H H CH2CH2 N C-H C-H C-H C-ClH H CH 2 CH 2 N C-H C-H C-H C-Cl
H H CH2CH2 C-H N C-H C-H C-HH H CH 2 CH 2 C-H N C-H C-H C-H
H H CH2CH2 C-H N C-Cl C-H C-HH H CH 2 CH 2 C-H N C-Cl C-H C-H
H H CH2CH2 C-H C-H N C-H C-HH H CH 2 CH 2 C-H C-H N C-H C-H
H H CH2CH2 N C-H C-H C-H NH H CH 2 CH 2 N C-H C-H C-H N
H H CH2CH2 N C-H C-H N C-HH H CH 2 CH 2 N C-H C-H N C-H
H H CH2CH2 C-Cl C-H N C-H C-HH H CH 2 CH 2 C-Cl C-H N C-H C-H
H H CH2CH2 C-H C-l C-H C-H C-HH H CH 2 CH 2 C-H C-1 C-H C-H C-H
H H CH2CH2 C-H C-OCHs C-H C-H C-HHH CH2CH2 C-H C-OCHs C-H C-H C-H
H H CH2CH2 C-H C-CFs C-H C-H C-HHH CH2CH2 C-H C-CFs C-H C-H C-H
H H CH2CH2 C-H C-CN C-H C-H C-HHH CH2CH2 C-H C-CN C-H C-H C-H
H H CH2CH2 C-CHs C-H C-H C-H C-CHsH H CH 2 CH 2 C-CHs C-H C-H C-H C-CHs
H H CH2CH2 C-Cl C-H C-H C-H C-ClH H CH 2 CH 2 C-Cl C-H C-H C-H C-Cl
H H CH2CH2 C-H C-Cl C-H C-Cl C-HH H CH 2 CH 2 C-H C-Cl C-H C-Cl C-H
H H CH2CH2 C-H C-SCFs C-H C-H C-HHH CH2CH2 C-H C-SCFs C-H C-H C-H
H H CH2CH2 C-H C-OCFs C-H C-H C-HHH CH2CH2 C-H C-OCFs C-H C-H C-H
H H CH2CH2 C-H C-OEt C-H C-H C-HHH CH2CH2 C-H C-OEt C-H C-H C-H
H H - C-H C-H C-OH C-H C-HH H -C-H C-H C-OH C-H C-H
H H - C-H C-OH C-OCHs C-Cl C-HH3 CHs - C-H C-H C-H C-H C-HHH - CH C - OH C - OCHs C - Cl C - HH 3 CHs - CH CH CH CH CH
H H - C-H C-H C-NMe2 C-H C-HHH - CH CH C-NMe 2 CH CH
H H - C-H C-CHs C-OCHs C-H C-HHH - C-H C-CHs C-OCHs C-H C-H
H H - C-H C-Cl C-OCHs C-H C-HHH - C-H C-Cl C-OCHs C-H C-H
H H - N C-H C-CHs N C-HH H - N C-H C-CHs N C-H
H H - N C-H C-Cl N C-H R5 R6 Y A1 A2 A3 A4 A5 HH - N CH C -ClNCH R 5 R 6 YA 1 A 2 A 3 A 4 A 5
CO2CH3 H CH2 C-H C-H C-H C-H C-HCO2CH3 H CH 2 CH CH CH CH CH
CO2CH3 H CH2 C-Cl C-H C-H C-H C-HCO2CH3 H CH 2 C-Cl CH CH CH CH
CO2CH3 H CH2 C-H C-Cl C-H C-H C-HCO2CH3 H CH 2 CH C-Cl CH CH CH
CO2CH3 H CH2 C-H C-H C-Cl C-H C-HCO2CH3 H CH 2 CH CH C-Cl CH CH
CO2CH3 H CH2 C-F C-H C-H C-H C-HCO2CH3 H CH 2 CF CH CH CH CH
CO2CH3 H CH2 C-H C-F C-H C-H C-HCO2CH3 H CH 2 CF CH CH CH CH
CO2CH3 H CH2 C-H C-H C-F C-H C-HCO2CH3 H CH 2 CH CH CH CF CH
CO2CH3 H CH2 C-Cl C-H C-Cl C-H C-ClCO2CH3 H CH 2 C-Cl CH C-Cl CH C-Cl
CO2CH3 H CH2 C-H C-H C-Br C-H C-HCO2CH3 H CH 2 CH CH C-Br CH CH
CO2CH3 H CH2 C-H C-H C-l C-H C-HCO2CH3 H CH 2 CH CH CH CH Cl
CO2CH3 H CH2 C-H C-H C-OCH3 C-H C-HCO2CH3 H CH 2 CH CH CH CH C-OCH3
CO2CH3 H CH2 C-H C-H C-CN C-H C-HCO2CH3 H CH 2 CH CH C-CN CH CH
CO2CH3 H CH2 C-H C-Cl C-H C-Cl C-HCO2CH3 H CH 2 CH C-Cl CH C-Cl CH
CO2Et H CH2 C-H C-H C-H C-H C-HCO 2 EtH CH 2 CH CH CH CH CH
CO2Et H CH2 C-Cl C-H C-H C-H C-HCO 2 EtH CH 2 C-Cl CH CH CH CH
CO2Et H CH2 C-H C-Cl C-H C-H C-HCO 2 EtH CH 2 CH C-Cl CH CH CH
CO2Et H CH2 C-H C-H C-Cl C-H C-HCO 2 EtH CH 2 CH CH C-Cl CH CH
CO2Et H CH2 C-F C-H C-H C-H C-HCO 2 EtH CH 2 CF CH CH CH CH
CO2Et H CH2 C-H C-F C-H C-H C-HCO 2 EtH CH 2 CH CF CH CH CH
CO2Et H CH2 C-H C-H C-F C-H C-HCO 2 EtH CH 2 CH CH CF CH CH
CO2Et H CH2 C-Cl C-H C-Cl C-H C-ClCO 2 Et H CH 2 C-Cl CH C-Cl CH C-Cl
CO2Et H CH2 C-H C-H C-Br C-H C-HCO 2 EtH CH 2 CH CH C-Br CH CH
CO2Et H CH2 C-H C-H C-l C-H C-HCO 2 EtH CH 2 CHCl Cl CH CH
CO2Et H CH2 C-H C-H C-OCH3 C-H C-HCO 2 EtH CH 2 CH CH C-OCH 3 CH CH
CO2Et H CH2 C-H C-H C-CN C-H C-HCO 2 EtH CH 2 CH CH C-CN CH CH
CO2Et H CH2 C-H C-Cl C-H C-Cl C-HCO 2 EtH CH 2 CH C-Cl CH C-Cl CH
CO2Et H CH2 N C-H C-H C-H C-HCO 2 EtH CH 2 N CH CH CH CH
CO2CH3 H CH2 N C-H C-H C-H C-HCO2CH3 H CH 2 N CH CH CH CH
CO2Et H - N C-H C-H C-H C-HCO 2 EtH - N CH CH CH CH
CO2CH3 H - N C-H C-H C-H C-HCO2CH3 H - N C-H C-H C-H C-H
CO2Et H CH2 C-H N C-H C-H C-H No. R5 R6 Y A1 A2 A3 A4 A5 CO 2 EtH CH 2 CH N CH CH CH No. R 5 R 6 YA 1 A 2 A 3 A 4 A 5
0 0
584 _rS H CH2 C-H C-H C-Br C-H C-H 584 _rS H CH 2 CH CH C-Br CH CH
0 0
585 _rS H CH2 C-H C-H C-l C-H C-H 585 _rS H CH 2 CH CH Cl CH CH
0 0
586 _rS H CH2 C-H C-Cl C-H C-H C-H 586 _rS H CH 2 CH C-Cl CH CH CH
0 0
587 H CH2 C-Cl C-H C-Cl C-H C-H o 587 H CH 2 C-Cl CH C-Cl CH CH o
588 6 H - C-H C-H C-H C-H C-H o 588 6 H - CH CH CH CH CH o
589 .6 H - C-H C-H C-Cl C-H C-H o 589. 6 H - CH CH C-Cl CH CH o
590 .6 H - C-H C-H C-Br C-H C-H o 590. 6 H - CH CH C-Br CH CH o
591 6 H - C-H C-H C-l C-H C-H o 591 6 H - CH CH Cl CH CH o
592 .6 H - C-H C-Cl C-H C-H C-H o 592. 6 H - CH C-Cl CH CH CH o
593 6 H - C-Cl C-H C-Cl C-H C-H 593 6 H - C-Cl CH C-Cl CH CH
No. R5 R6 Y A1 A2 A3 A4 A5 No. R 5 R 6 YA 1 A 2 A 3 A 4 A 5
C-C-
607 H H - C-H C-H C-H C-H 607 H H - C-H C-H C-H C-H
CO2Et CO 2 Et
C- C-
608 H H - C-H C-H C-H C-H 608 H H - C-H C-H C-H C-H
CO2Et CO 2 Et
609 H H - C-CO2H C-H C-H C-H C-H609 HH - C-CO 2 H CH CH CH CH
610 H H - C-H C-CO2H C-H C-H C-H610 HH - CH C-CO 2 H CH CH CH
61 1 H H CH2 C-H C-H C-H C-H C-H61 1 HH CH 2 CH CH CH CH CH
612 H H CH2 C-Cl C-H C-H C-H C-H612 HH CH 2 C-Cl CH CH CH CH
613 H H CH2 C-H C-Cl C-H C-H C-H613 HH CH 2 CH C-Cl CH CH CH
614 H H CH2 C-H C-H C-Cl C-H C-H614HH CH 2 CH CH C-Cl CH CH
615 H H CH2 C-Cl C-H C-Cl C-H C-H615 HH CH 2 C-Cl CH C-Cl CH CH
616 H H CH2 C-Cl C-H C-H C-Cl C-H616 HH CH 2 C-Cl CH CH C-Cl CH
617 H H CH2 C-F C-H C-H C-H C-H617HH CH 2 CF CH CH CH CH
618 H H CH2 C-H C-F C-H C-H C-H618HH CH 2 CH CF CH CH CH
619 H H CH2 C-H C-H C-F C-H C-H619HH CH 2 CH CH CF CH CH
620 H H CH2 C-F C-H C-F C-H C-H620HH CH 2 CF CH CF CH CH
621 H H CH2 C-H C-F C-H C-F C-H621 HH CH 2 CH CF CH CF CH
622 H H CH2 C-F C-H C-H C-H C-F622 HH CH 2 CF CH CH CH CF
623 H H CH2 C-Br C-H C-H C-H C-H623 HH CH 2 C-Br CH CH CH CH
624 H H CH2 C-H C-Br C-H C-H C-H624HH CH 2 CHC-Br CH CH CH
625 H H CH2 C-H C-H C-Br C-H C-H625HH CH 2 CH CH C-Br CH CH
626 H H CH2 C-l C-H C-H C-H C-H626 HH CH 2 Cl CH CH CH CH
627 H H CH2 C-OCHs C-H C-H C-H C-H627 HH CH 2 C-OCHs CH CH CH CH
628 H H CH2 C-CF3 C-H C-H C-H C-H628 HH CH 2 C-CF 3 CH CH CH CH
629 H H CH2 C-CH3 C-H C-H C-H C-H629 HH CH 2 C-CH 3 CH CH CH CH
630 H H CH2 C-CN C-H C-H C-H C-H630 HH CH 2 C-CN CH CH CH CH
631 H H CH2 C-H C-H C-l C-H C-H631 HH CH 2 CH CH Cl CH CH
632 H H CH2 C-H C-H C-OCHs C-H C-H632 HH CH 2 CH CH C-OCHs CH CH
633 H H CH2 C-H C-H C-CF3 C-H C-H633 HH CH 2 CH CH C-CF 3 CH CH
634 H H CH2 C-H C-H C-CH3 C-H C-H634 HH CH 2 CH CH C-CH 3 CH CH
635 H H CH2 C-H C-H C-CN C-H C-H No. R5 R6 Y A1 A2 A3 A4 A5 635 HH CH 2 CH CH C-CN CH CH No. R 5 R 6 YA 1 A 2 A 3 A 4 A 5
636 H H CH2 C-H C-H C-SCFs C-H C-H636 HH CH 2 CH CH C-SCF CH CH
637 H H CH2 C-H C-H C-OCFs C-H C-H637 HH CH 2 CH CH C -OCFs CH CH
638 H H CH2 C-H C-H C-OEt C-H C-H638 HH CH 2 CH CH C-OEt CH CH
639 H H CH2 C-H C-H C-t-Bu C-H C-H639 HH CH 2 CH CH Ct-Bu CH CH
640 H H CH2 C-F C-H C-Br C-H C-H640 HH CH 2 CF CH C-Br CH CH
641 H H CH2 N C-H C-H C-H C-H641HH CH 2 N CH CH CH CH
642 H H CH2 N C-Cl C-H C-H C-H642 HH CH 2 N C-Cl CH CH CH
643 H H CH2 N C-H C-Cl C-H C-H643 HH CH 2 N CH C-Cl CH CH
644 H H CH2 N C-H C-H C-H C-Cl644 HH CH 2 N CH CH CH C-Cl
645 H H CH2 C-H N C-H C-H C-H645HH CH 2 CHN CH CH CH
646 H H CH2 C-H N C-Cl C-H C-H646HH CH 2 CH N C-Cl CH CH
647 H H CH2 C-H C-H N C-H C-H647 HH CH 2 CH CH CH CH
648 H H CH2 N C-H C-H C-H N648HH CH 2 N CH CH CH N
649 H H CH2 N C-H C-H N C-H649 HH CH 2 N CH CH N CH
650 H H CH2 C-Cl C-H N C-H C-H650 HH CH 2 C-Cl CH N CH CH
651 H H CH2 C-H C-l C-H C-H C-H651 HH CH 2 CH Cl CH CH CH
652 H H CH2 C-H C-OCHs C-H C-H C-H652 HH CH 2 CH C-OCHs CH CH CH
653 H H CH2 C-H C-CF3 C-H C-H C-H653 HH CH 2 CH C-CF 3 CH CH CH
654 H H CH2 C-H C-CN C-H C-H C-H654HH CH 2 CHC-CN CH CH CH
655 H H CH2 C-CH3 C-H C-H C-H C-CHs655 HH CH 2 C-CH 3 CH CH CH C-CHs
656 H H CH2 C-Cl C-H C-H C-H C-Cl656 HH CH 2 C-Cl CH CH CH C-Cl
657 H H CH2 C-H C-Cl C-H C-Cl C-H657 HH CH 2 CH C-Cl CH C-Cl CH
658 H H CH2 C-H C-SCFs C-H C-H C-H658 HH CH 2 CH C-SCFs CH CH CH
659 H H CH2 C-H C-OCFs C-H C-H C-H659 HH CH 2 CH C-OCFs CH CH CH
660 H H CH2 C-H C-OEt C-H C-H C-H660HH CH 2 CH C-OEt CH CH CH
661 H H CH2 C-H C-OCHs C-OCHs C-OCHs C-H661 HH CH 2 CH C-OCHs C-OCHs C-OCHs CH
662 H H CH2 C-H C-OCHs C-OCHs C-H C-H662 HH CH 2 CH C-OCHs C-OCHs CH CH
663 H H CH2 C-H C-CH3 C-CHs C-H C-H663 HH CH 2 CH C-CH 3 C-CHs CH CH
664 H H CH2 C-CH3 C-H C-CHs C-H C-H664 HH CH 2 C-CH 3 CH C-CHs CH CH
665 H H CH2 C-CH3 C-H C-CHs C-H C-CHs665 HH CH 2 C-CH 3 CH C-CHs CH C-CHs
666 H H CH2 C-Et C-H C-CHs C-H C-H No. R5 R6 Y A1 A2 A3 A4 A5 666 HH CH 2 C-Et CH C-CHs CH CH No. R 5 R 6 YA 1 A 2 A 3 A 4 A 5
667 H H CH2 C-NO2 C-H C-H C-H C-H667 HH CH 2 C-NO 2 CH CH CH CH
668 H H CH2 C-H C-NO2 C-H C-H C-H668 HH CH 2 CH C-NO 2 CH CH CH
669 H H CH2 C-H C-H C-NO2 C-H C-H 669 HH CH 2 CH CH C-NO 2 CH CH
670 H H CH2 C-H C-H C-H 670HH CH 2 CH CH CH
671 H H - C-CHF2 C-H C-H C-H C-H671 HH - C-CHF 2 CH CH CH CH
672 H H - C-H C-CHF2 C-H C-H C-H672 HH - CH C-CHF 2 CH CH CH
673 H H - C-H C-H C-CHF2 C-H C-H673 HH - CH CH C-CHF 2 CH CH
674 H H - C-CH3 C-CH3 C-CH3 C-CH3 C-CH3 674 HH - C-CH 3 C-CH 3 C-CH 3 C-CH 3 C-CH 3
675 H H - C-F C-F C-F C-F C-F 675 H H - C-F C-F C-F C-F C-F
C- C-
676 H H - C-H C-H C-H C-H 676 H H - C-H C-H C-H C-H
OCHF2 OCHF 2
C- C-
677 H H - C-H C-H C-H C-H 677 H H - C-H C-H C-H C-H
OCHF2 OCHF 2
C- C-
678 H H - C-H C-H C-H C-H 678 H H - C-H C-H C-H C-H
OCHF2 OCHF 2
679 H H - C-CN N C-H C-H C-H 679 H H - C-CN N C-H C-H C-H
680 H H - C-Cl C-Cl C-CF3 C-Cl C-Cl680 HH - C-Cl C-Cl C-CF 3 C-Cl C-Cl
681 H H - C-H N C-Cl C-H C-Cl 681 H H - C-H N C-Cl C-H C-Cl
A2. Verbindungen A2-1 bis A2-681 der allgemeinen Formel (Ia2), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen A2-1 bis A2-681 ) in der oben stehenden Tabelle 1 entsprechen. A2. Compounds A2-1 to A2-681 of the general formula (Ia2) in which R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 correspond to the definitions (Nos 1 to 681; 1 to A2-681) in Table 1 above.
(Ia2)(Ia2)
A3. Verbindungen A3-1 bis A3-681 der allgemeinen Formel (Ia3), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen A3-1 bis A3-681 ) in der oben stehenden Tabelle 1 entsprechen. A3. Compounds A3-1 to A3-681 of the general formula (Ia3) in which R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 correspond to the definitions (Nos 1 to 681; 1 to A3-681) in Table 1 above.
A4. Verbindungen A4-1 bis A4-681681 der allgemeinen Formel (Ia4), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen A4-1 bis A4-681 ) in der oben stehenden Tabelle 1 entsprechen. A4. Compounds A4-1 to A4-681681 of the general formula (Ia4) in which R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 correspond to the definitions (Nos 1 to 681; 1 to A4-681) in Table 1 above.
A5. Verbindungen A5-1 bis A5-681 der allgemeinen Formel (Ia5), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen A5-1 bis A5-681 ) in der oben stehenden Tabelle 1 entsprechen. A5. Compounds A5-1 to A5-681 of the general formula (Ia5) in which R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 are as defined (Nos 1 to 681, corresponding to compounds A5- 1 to A5-681) in Table 1 above.
A6. Verbindungen A6-1 bis A6-681 der allgemeinen Formel (Ia6), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen A6-1 bis A6-681 ) in der oben stehenden Tabelle 1 entsprechen. A6. Compounds A6-1 to A6-681 of the general formula (Ia6) in which R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 correspond to the definitions (Nos 1 to 681, corresponding to compounds A6- 1 to A6-681) in Table 1 above.
(Ia6)(Ia6)
A7. Verbindungen A7-1 bis A7-681 der allgemeinen Formel (Ia7), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen A7-1 bis A7-681 ) in der oben stehenden Tabelle 1 entsprechen. A7. Compounds A7-1 to A7-681 of the general formula (Ia7) in which R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 correspond to the definitions (Nos 1 to 681; 1 to A7-681) in Table 1 above.
A8. Verbindungen A8-1 bis A8-681 der allgemeinen Formel (Ia8), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen A8-1 bis A8-681 ) in der oben stehenden Tabelle 1 entsprechen. A8. Compounds A8-1 to A8-681 of the general formula (Ia8) in which R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 are as defined (Nos 1 to 681; 1 to A8-681) in Table 1 above.
A9. Verbindungen A9-1 bis A9-681 der allgemeinen Formel (Ia9), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen A9-1 bis A9-681 ) in der oben stehenden Tabelle 1 entsprechen. A9. Compounds A9-1 to A9-681 of the general formula (Ia9) in which R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 are as defined (Nos 1 to 681; 1 to A9-681) in Table 1 above.
A10. Verbindungen A10-1 bis A10-681 der allgemeinen Formel (Ia10), worin R5, R6, Y A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen A10-1 bis A10-681 ) in der oben stehenden Tabelle 1 entsprechen. A10. Compounds A10-1 to A10-681 of the general formula (Ia10) in which R 5 , R 6 , YA 1 , A 2 , A 3 , A 4 , A 5 are as defined (Nos 1 to 681, corresponding to compounds A10-1 to A10-681) in Table 1 above.
(Ia10)(Ia10)
A1 1 . Verbindungen A1 1 -1 bis A1 1 -681 der allgemeinen Formel (Ia1 1 ), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen A1 1 -1 bis A1 1 -681 ) in der oben stehenden Tabelle 1 entsprechen. A1 1. Compounds A1 1 -1 to A1 1 -681 of the general formula (Ia1 1), wherein R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 are the definitions (Nos 1 to 681; Compounds A1 1 -1 to A1 1 -681) in Table 1 above.
A12. Verbindungen A12-1 bis A12-681 der allgemeinen Formel (If1 ), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen A12-1 bis A12-681 ) in der oben stehenden Tabelle 1 entsprechen. A12. Compounds A12-1 to A12-681 of the general formula (If1) in which R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 are as defined (Nos 1 to 681, corresponding to compounds A12- 1 to A12-681) in Table 1 above.
A13. Verbindungen A13-1 bis A13-681 der allgemeinen Formel (If2), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen A13-1 bis A13-681 ) in der oben stehenden Tabelle 1 entsprechen. A13. Compounds A13-1 to A13-681 of the general formula (If2) in which R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 are as defined (Nos 1 to 681, corresponding to compounds A13- 1 to A13-681) in Table 1 above.
A14. Verbindungen A14-1 bis A14-681 der allgemeinen Formel (If3), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen A14-1 bis A14-681 ) in der oben stehenden Tabelle 1 entsprechen. A14. Compounds A14-1 to A14-681 of the general formula (If3) in which R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 correspond to the definitions (Nos 1 to 681, corresponding to compounds A14- 1 to A14-681) in the above Table 1.
A15. Verbindungen A15-1 bis A15-681 der allgemeinen Formel (lo1 ), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen A15-1 bis A15-681 ) in der oben stehenden Tabelle 1 entsprechen. A15. Compounds A15-1 to A15-681 of the general formula (Io1) in which R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 correspond to the definitions (Nos 1 to 681; 1 to A15-681) in Table 1 above.
A16. Verbindungen A16-1 bis A16-681 der allgemeinen Formel (lo2), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen A16-1 bis A16-681 ) in der oben stehenden Tabelle 1 entsprechen. A16. Compounds A16-1 to A16-681 of the general formula (lo2) in which R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 correspond to the definitions (Nos 1 to 681; 1 to A16-681) in the above Table 1.
A17. Verbindungen A17-1 bis A17-681 der allgemeinen Formel (lo3), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen A17-1 bis A17-681 ) in der oben stehenden Tabelle 1 entsprechen. A17. Compounds A17-1 to A17-681 of the general formula (lo3) in which R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 correspond to the definitions (Nos 1 to 681; 1 to A17-681) in Table 1 above.
(lo3)(Lo3)
A18. Verbindungen A18-1 bis A18-681 der allgemeinen Formel (lo4), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen A18-1 bis A18-681 ) in der oben stehenden Tabelle 1 entsprechen. A18. Compounds A18-1 to A18-681 of the general formula (lo4) in which R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 correspond to the definitions (Nos 1 to 681, corresponding to compounds A18- 1 to A18-681) in Table 1 above.
A19. Verbindungen A19-1 bis A19-681 der allgemeinen Formel (lo5), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen A19-1 bis A19-681 ) in der oben stehenden Tabelle 1 entsprechen. A19. Compounds A19-1 to A19-681 of the general formula (lo5) in which R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 correspond to the definitions (Nos 1 to 681; 1 to A19-681) in Table 1 above.
A20. Verbindungen A20-1 bis A20-681 der allgemeinen Formel (lo6), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen A20-1 bis A20-681 ) in der oben stehenden Tabelle 1 entsprechen. A20. Compounds A20-1 to A20-681 of the general formula (lo6) in which R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 correspond to the definitions (Nos 1 to 681, corresponding to compounds A20- 1 to A20-681) in Table 1 above.
A21 . Verbindungen A21 -1 bis A21 -681 der allgemeinen Formel (Ie1 ), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen A21 -1 bis A21 -681 ) in der oben stehenden Tabelle 1 entsprechen. A21. Compounds A21-1 to A21 -681 of the general formula (Ie1) in which R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 correspond to the definitions (Nos 1 to 681; 1 to A21 -681) in Table 1 above.
(Ie1 )(Ie1)
A22. Verbindungen A22-1 bis A22-681 der allgemeinen Formel (Ie2), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen A22-1 bis A22-681 ) in der oben stehenden Tabelle 1 entsprechen. A22. Compounds A22-1 to A22-681 of the general formula (Ie2) in which R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 correspond to the definitions (Nos 1 to 681; 1 to A22-681) in Table 1 above.
A23. Verbindungen A23-1 bis A23-681 der allgemeinen Formel (Ie3), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen A23-1 bis A23-681 ) in der oben stehenden Tabelle 1 entsprechen. A23. Compounds A23-1 to A23-681 of the general formula (Ie3) in which R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 correspond to the definitions (Nos 1 to 681, corresponding to compounds A23- 1 to A23-681) in Table 1 above.
A24. Verbindungen A24-1 bis A24-681 der allgemeinen Formel (lo7), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen A24-1 bis A24-681 ) in der oben stehenden Tabelle 1 entsprechen. A24. Compounds A24-1 to A24-681 of the general formula (lo7) in which R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 correspond to the definitions (Nos 1 to 681; 1 to A24-681) in the above Table 1.
B1 . Verbindungen B1 -1 bis B1 -681 der allgemeinen Formel (Ia1 1 ), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen B1 -1 bis B1 -681 ) in der oben stehenden Tabelle 1 entsprechen. B1. Compounds B1 -1 to B1 -681 of the general formula (Ia1 1) in which R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 satisfy the definitions (Nos 1 to 681, corresponding to compounds B1 -1 to B1 -681) in Table 1 above.
(Ia11 )(Ia11)
B2. Verbindungen B2-1 bis B2-681 der allgemeinen Formel (Ia12), worin R5, R6, Y, A1 A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen B2-1 bis B2-681 ) in der oben stehenden Tabelle 1 entsprechen. B2. Compounds B2-1 to B2-681 of the general formula (Ia12) in which R 5 , R 6 , Y, A 1 A 2 , A 3 , A 4 , A 5 satisfy the definitions (Nos 1 to 681, corresponding to compounds B2-1 to B2-681) in Table 1 above.
B3. Verbindungen B3-1 bis B3-681 der allgemeinen Formel (Ia13), worin R5, R6, Y, A1 A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen B3-1 bis B3-681 ) in der oben stehenden Tabelle 1 entsprechen. B3. Compounds B3-1 to B3-681 of the general formula (Ia13), wherein R 5 , R 6 , Y, A 1 A 2 , A 3 , A 4 , A 5 are the definitions (Nos 1 to 681, corresponding to compounds B3-1 to B3-681) in Table 1 above.
B4. Verbindungen B4-1 bis B4-681 der allgemeinen Formel (Ia14), worin R5, R6, Y, A1 A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen B4-1 bis B4-681 ) in der oben stehenden Tabelle 1 entsprechen. B4. Compounds B4-1 to B4-681 of the general formula (Ia14) in which R 5 , R 6 , Y, A 1 A 2 , A 3 , A 4 , A 5 satisfy the definitions (Nos 1 to 681, corresponding to compounds B4-1 to B4-681) in Table 1 above.
B5. Verbindungen B5-1 bis B5-681 der allgemeinen Formel (lo8), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen B5-1 bis B5-681 ) in der oben stehenden Tabelle 1 entsprechen. B5. Compounds B5-1 to B5-681 of the general formula (lo8) in which R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 correspond to the definitions (Nos 1 to 681, corresponding to compounds B5- 1 to B5-681) in Table 1 above.
(lo8)(Lo8)
C1 . Verbindungen C1 -1 bis C1 -681 der allgemeinen Formel (Ia15), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen C1 -1 bis C1 -681 ) in der oben stehenden Tabelle 1 entsprechen. C1. Compounds C1 -1 to C1 -681 of the general formula (Ia15) in which R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 correspond to the definitions (Nos 1 to 681; 1 to C1 -681) in the above Table 1.
C2. Verbindungen C2-1 bis C2-681 der allgemeinen Formel (Ia16), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen C2-1 bis C2-681 ) in der oben stehenden Tabelle 1 entsprechen. C2. Compounds C2-1 to C2-681 of the general formula (Ia16) in which R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 correspond to the definitions (Nos 1 to 681; 1 to C2-681) in Table 1 above.
C3. Verbindungen C3-1 bis C3-681 der allgemeinen Formel (Ia17), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen C3-1 bis C3-681 ) in der oben stehenden Tabelle 1 entsprechen. C3. Compounds C3-1 to C3-681 of the general formula (Ia17) in which R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 correspond to the definitions (Nos 1 to 681; 1 to C3-681) in Table 1 above.
C4. Verbindungen C4-1 bis C4-681 der allgemeinen Formel (lo9), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen C4-1 bis C4-681 ) in der oben stehenden Tabelle 1 entsprechen. C4. Compounds C4-1 to C4-681 of the general formula (lo9) in which R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 correspond to the definitions (Nos 1 to 681; 1 to C4-681) in Table 1 above.
(lo9)(Lo9)
C5. Verbindungen C5-1 bis C5-681 der allgemeinen Formel (Ia18), worin R5, R6, Y, A1 A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen C5-1 bis C5-681 ) in der oben stehenden Tabelle 1 entsprechen. C5. Compounds C5-1 to C5-681 of the general formula (Ia18) in which R 5 , R 6 , Y, A 1 A 2 , A 3 , A 4 , A 5 are as defined (Nos 1 to 681, corresponding to compounds C5-1 to C5-681) in Table 1 above.
D1 . Verbindungen D1 -1 bis D1 -681 der allgemeinen Formel (Ia19), worin R5, R6, Y, A1 A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen D1 -1 bis D1 -681 ) in der oben stehenden Tabelle 1 entsprechen. D1. Compounds D1 -1 to D1 -681 of the general formula (Ia19) in which R 5 , R 6 , Y, A 1 A 2 , A 3 , A 4 , A 5 satisfy the definitions (Nos 1 to 681, corresponding to compounds D1 -1 to D1 -681) in Table 1 above.
D2. Verbindungen D2-1 bis D2-681 der allgemeinen Formel (Io10), worin R5, R6, Y, A1 A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen D1 -1 bis D1 -681 ) in der oben stehenden Tabelle 1 entsprechen. D2. Compounds D2-1 to D2-681 of the general formula (Io10) in which R 5 , R 6 , Y, A 1 A 2 , A 3 , A 4 , A 5 satisfy the definitions (Nos 1 to 681, corresponding to compounds D1 -1 to D1 -681) in Table 1 above.
D3. Verbindungen D3-1 bis D3-681 der allgemeinen Formel (Ia20), worin R5, R6, Y, A1 A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen D3-1 bis D3-681 ) in der oben stehenden Tabelle 1 entsprechen. D3. Compounds D3-1 to D3-681 of the general formula (Ia20) in which R 5 , R 6 , Y, A 1 A 2 , A 3 , A 4 , A 5 are as defined (Nos 1 to 681, corresponding to compounds D3-1 to D3-681) in Table 1 above.
D4. Verbindungen D4-1 bis D4-681 der allgemeinen Formel (Ia21 ), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen D4-1 bis D4-681 ) in der oben stehenden Tabelle 1 entsprechen. D4. Compounds D4-1 to D4-681 of the general formula (Ia21) in which R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 correspond to the definitions (Nos 1 to 681, corresponding to compounds D4- 1 to D4-681) in the above Table 1.
D5. Verbindungen D5-1 bis D5-681 der allgemeinen Formel (Ia22), worin R5, R6, Y, A1 A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen D5-1 bis D5-681 ) in der oben stehenden Tabelle 1 entsprechen. D5. Compounds D5-1 to D5-681 of the general formula (Ia22) in which R 5 , R 6 , Y, A 1 A 2 , A 3 , A 4 , A 5 correspond to the definitions (Nos 1 to 681, corresponding to compounds D5-1 to D5-681) in Table 1 above.
D6. Verbindungen D6-1 bis D6-681 der allgemeinen Formel (Ia23), worin R5, R6, Y, A1 A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen D6-1 bis D6-681 ) in der oben stehenden Tabelle 1 entsprechen. D6. Compounds D6-1 to D6-681 of the general formula (Ia23) in which R 5 , R 6 , Y, A 1 A 2 , A 3 , A 4 , A 5 correspond to the definitions (Nos 1 to 681, corresponding to compounds D6-1 to D6-681) in Table 1 above.
E1 . Verbindungen E1 -1 bis E1 -681 der allgemeinen Formel (Ia24), worin R5, R6, Y, A1 A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen E1 -1 bis E1 -681 ) in der oben stehenden Tabelle 1 entsprechen. E1. Compounds E1 -1 to E1 -681 of the general formula (Ia24) in which R 5 , R 6 , Y, A 1 A 2 , A 3 , A 4 , A 5 satisfy the definitions (Nos 1 to 681, corresponding to compounds E1 -1 to E1 -681) in Table 1 above.
E2. Verbindungen E2-1 bis E2-681 der allgemeinen Formel (Id1 ), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen E2-1 bis E2-681 ) in der oben stehenden Tabelle 1 entsprechen. E2. Compounds E2-1 to E2-681 of the general formula (Id1) in which R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 are as defined (Nos 1 to 681, corresponding to compounds E2- 1 to E2-681) in Table 1 above.
E3. Verbindungen E3-1 bis E3-681 der allgemeinen Formel (If4), worin R5, R6, Y, A1 A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen E3-1 bis E3-681 ) in der oben stehenden Tabelle 1 entsprechen. E3. Compounds E3-1 to E3-681 of the general formula (If4) in which R 5 , R 6 , Y, A 1 A 2 , A 3 , A 4 , A 5 correspond to the definitions (Nos 1 to 681, corresponding to compounds E3-1 to E3-681) in Table 1 above.
E4. Verbindungen E4-1 bis E4-681 der allgemeinen Formel (Ie4), worin R5, R6, Y, A1 A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen E4-1 bis E4-681 ) in der oben stehenden Tabelle 1 entsprechen. E4. Compounds E4-1 to E4-681 of the general formula (Ie4) in which R 5 , R 6 , Y, A 1 A 2 , A 3 , A 4 , A 5 have the definitions (Nos 1 to 681, corresponding to compounds E4-1 to E4-681) in Table 1 above.
(Ie4)(Ie4)
E5. Verbindungen E5-1 bis E5-681 der allgemeinen Formel (lo1 1 ), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen E5-1 bis E5-681 ) in der oben stehenden Tabelle 1 entsprechen. E5. Compounds E5-1 to E5-681 of the general formula (Io1) in which R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 are as defined (Nos 1 to 681, corresponding to compounds E5 -1 to E5-681) in Table 1 above.
F1 . Verbindungen F1 -1 bis F1 -681 der allgemeinen Formel (Ia25), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen F1 -1 bis F1 -681 ) in der oben stehenden Tabelle 1 entsprechen. F1. Compounds F1 -1 to F1 -681 of the general formula (Ia25) in which R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 correspond to the definitions (Nos 1 to 681; 1 to F1 -681) in Table 1 above.
F2. Verbindungen F2-1 bis F2-681 der allgemeinen Formel (Ia26), worin R5, R6, Y, A1 A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen F2-1 bis F2-681 ) in der oben stehenden Tabelle 1 entsprechen. F2. Compounds F2-1 to F2-681 of the general formula (Ia26) in which R 5 , R 6 , Y, A 1 A 2 , A 3 , A 4 , A 5 satisfy the definitions (Nos 1 to 681, corresponding to compounds F2-1 to F2-681) in Table 1 above.
G1 . Verbindungen G1 -1 bis G1 -681 der allgemeinen Formel (Ia27), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen G1 -1 bis G1 -681 ) in der oben stehenden Tabelle 1 entsprechen. G1. Compounds G1 -1 to G1 -681 of the general formula (Ia27) in which R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 correspond to the definitions (Nos 1 to 681; 1 to G1 -681) in Table 1 above.
(Ia27)(Ia27)
G2. Verbindungen G2-1 bis G2-681 der allgemeinen Formel (Ia28), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen G2-1 bis G2-681 ) in der oben stehenden Tabelle 1 entsprechen. G2. Compounds G2-1 to G2-681 of the general formula (Ia28) in which R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 correspond to the definitions (Nos 1 to 681; 1 to G2-681) in Table 1 above.
G3. Verbindungen G3-1 bis G3-681 der allgemeinen Formel (If5), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen G3-1 bis G3-681 ) in der oben stehenden Tabelle 1 entsprechen. G3. Compounds G3-1 to G3-681 of the general formula (If5) in which R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 correspond to the definitions (Nos 1 to 681; 1 to G3-681) in Table 1 above.
G4. Verbindungen G4-1 bis G4-681 der allgemeinen Formel (Ie5), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen G4-1 bis G4-681 ) in der oben stehenden Tabelle 1 entsprechen. G4. Compounds G4-1 to G4-681 of the general formula (Ie5) in which R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 are as defined (Nos 1 to 681, corresponding to compounds G4- 1 to G4-681) in Table 1 above.
G5. Verbindungen G5-1 bis G5-681 der allgemeinen Formel (lo12), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen G5-1 bis G5-681 ) in der oben stehenden Tabelle 1 entsprechen. G5. Compounds G5-1 to G5-681 of the general formula (Io12) in which R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 correspond to the definitions (Nos 1 to 681, corresponding to compounds G5- 1 to G5-681) in Table 1 above.
(lo12)(LO12)
G6. Verbindungen G6-1 bis G6-681 der allgemeinen Formel (lo13), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen G6-1 bis G6-681 ) in der oben stehenden Tabelle 1 entsprechen. G6. Compounds G6-1 to G6-681 of the general formula (Io13) in which R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 correspond to the definitions (Nos 1 to 681; 1 to G6-681) in Table 1 above.
G7. Verbindungen G7-1 bis G7-681 der allgemeinen Formel (Ia29), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen G7-1 bis G7-681 ) in der oben stehenden Tabelle 1 entsprechen. G7. Compounds G7-1 to G7-681 of the general formula (Ia29) in which R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 correspond to the definitions (Nos 1 to 681; 1 to G7-681) in Table 1 above.
G8. Verbindungen G8-1 bis G8-681 der allgemeinen Formel (Ia30), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen G8-1 bis G8-681 ) in der oben stehenden Tabelle 1 entsprechen. G8. Compounds G8-1 to G8-681 of the general formula (Ia30) in which R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 correspond to the definitions (Nos 1 to 681, corresponding to compounds G8- 1 to G8-681) in Table 1 above.
G9. Verbindungen G9-1 bis G9-681 der allgemeinen Formel (lo14), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen G9-1 bis G9-681 ) in der oben stehenden Tabelle 1 entsprechen. G9. Compounds G9-1 to G9-681 of the general formula (lo14) in which R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 are as defined (Nos 1 to 681; 1 to G9-681) in Table 1 above.
(lo14)(Lo14)
G10. Verbindungen G10-1 bis G10-681 der allgemeinen Formel (Ia31 ), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen G10- 1 bis G10-681 ) in der oben stehenden Tabelle 1 entsprechen. G10. Compounds G10-1 to G10-681 of the general formula (Ia31) in which R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 are as defined (Nos 1 to 681, corresponding to compounds G10- 1 to G10-681) in the above Table 1.
G1 1 . Verbindungen G1 1 -1 bis G1 1 -681 der allgemeinen Formel (Ia32), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen G1 1 - 1 bis G1 1 -681 ) in der oben stehenden Tabelle 1 entsprechen. G1 1. Compounds G1 1 -1 to G1 1 -681 of the general formula (Ia32) in which R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 are as defined (Nos 1 to 681; G1 1 - 1 to G1 1 -681) in Table 1 above.
H1 . Verbindungen H1 -1 bis H1 -681 der allgemeinen Formel (Ia33), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen H1 -1 bis H1 -681 ) in der oben stehenden Tabelle 1 entsprechen. H1. Compounds H1 -1 to H1 -681 of the general formula (Ia33) in which R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 correspond to the definitions (Nos 1 to 681; 1 to H1 -681) in Table 1 above.
H2. Verbindungen H2-1 bis H2-681 der allgemeinen Formel (lo15), worin R5, R6, Y, A1, A2, A3, A4, A5 den Definitionen (Nos 1 bis 681 ; entsprechend Verbindungen H2-1 bis H2-681 ) in der oben stehenden Tabelle 1 entsprechen. H2. Compounds H2-1 to H2-681 of the general formula (Io15) in which R 5 , R 6 , Y, A 1 , A 2 , A 3 , A 4 , A 5 correspond to the definitions (Nos 1 to 681; 1 to H2-681) in Table 1 above.
(lo15)(LO15)
Spektroskopische Daten ausgewählter Tabellenbeispiele: Spectroscopic data of selected table examples:
Die nachfolgend aufgeführten spektroskopischen Daten ausgewählter The spectroscopic data of selected
Tabellenbeispiele wurden über klassische 1H-NMR-lnterpretation oder über Table examples were obtained by classical 1 H-NMR interpretation or
NMR-Peak-Listenverfahren ausgewertet. a) klassische 1H-NMR-lnterpretation Beispiel No. A2-4: NMR peak list method evaluated. a) classical 1 H-NMR interpretation A2-4:
1H-NMR (400 MHz, CDCIs δ, ppm) 7.69 (m, 1 H), 7.57 (m, 1 H), 7.28-7.24 (m, 1 H), 5.26 (s, 2H), 3.77 (s, 3H), 3.41 (s, 6H). 1 H-NMR (400 MHz, CDCIs δ, ppm) 7.69 (m, 1H), 7.57 (m, 1H), 7.28-7.24 (m, 1H), 5.26 (s, 2H), 3.77 (s, 3H), 3.41 (s, 6H).
Beispiel No. A2-61 : Example No. A2-61:
1H-NMR (400 MHz, CDCI3 δ, ppm) 7.91 (m, 1 H), 7.75 (m, 1 H), 7.65 (m, 1 H), 7.57 (m, 1 H), 5.25 (s, 2H), 3.76 (s, 3H), 3.45 (s, 6H). 1H-NMR (400 MHz, CDCl3 δ, ppm) 7.91 (m, 1H), 7.75 (m, 1H), 7.65 (m, 1H), 7.57 (m, 1H), 5.25 (s, 2H) , 3.76 (s, 3H), 3.45 (s, 6H).
Beispiel No. A4-1 : Example No. A4-1:
1H-NMR (400 MHz, CDCI3 δ, ppm) 7.71 -7.66 (m, 2H), 7.45 (m, 1 H), 7.39-7.35 (m, 1 H), 7.32-7.27 (m, 1 H), 5.24 (s, 2H), 3.90 (s, 3H), 3.38 (s, 6H). 1 H-NMR (400 MHz, CDCl3 δ, ppm) 7.71-7.66 (m, 2H), 7.45 (m, 1H), 7.39-7.35 (m, 1H), 7.32-7.27 (m, 1H), 5.24 (s, 2H), 3.90 (s, 3H), 3.38 (s, 6H).
Beispiel No. A4-61 : Example No. A4-61:
1H-NMR (400 MHz, CDCI3 δ, ppm) 7.84 (m, 1 H), 7.75 (m, 1 H), 7.68 (s, 1 H), 7.65-7.60 (m, 1 H), 7.56-7.52 (m, 1 H), 5.29 (s, 2H), 3.89 (s, 3H), 3.43 (s, 6H). 1 H-NMR (400 MHz, CDCl3 δ, ppm) 7.84 (m, 1H), 7.75 (m, 1H), 7.68 (s, 1H), 7.65-7.60 (m, 1H), 7.56-7.52 (m, 1H), 5.29 (s, 2H), 3.89 (s, 3H), 3.43 (s, 6H).
Beispiel No. A7-61 : Example No. A7-61:
1H-NMR (400 MHz, CDCI3 δ, ppm) 7.84 (m, 1 H), 7.76 (m, 1 H), 7.65 (m, 1 H), 7.57 (m, 1 H), 7.25-6.96 (br. t, 1 H, CHF2), 5.24 (s, 2H), 4.1 1 (m, 2H), 3.45 (s, 6H), 1 .47 (t, 3H). Beispiel No. A8-1 : 1 H-NMR (400 MHz, CDCl3 δ, ppm) 7.84 (m, 1H), 7.76 (m, 1H), 7.65 (m, 1H), 7.57 (m, 1H), 7.25-6.96 (br t, 1H, CHF 2 ), 5.24 (s, 2H), 4.1 1 (m, 2H), 3.45 (s, 6H), 1.47 (t, 3H). Example No. A8-1:
1H-NMR (400 MHz, CDCI3 δ, ppm) 7.72 (s, 1 H), 7.58 (m, 1 H), 7.47 (m, 1 H), 7.38 (m, 1 H), 7.36-7.18 (br. t, 1 H, CHF2), 7.30 (m, 1 H), 5.24 (s, 2H), 3.92 (s, 3H), 3.39 (s, 6H). Beispiel No. A8-4: 1 H-NMR (400 MHz, CDCl3 δ, ppm) 7.72 (s, 1H), 7.58 (m, 1H), 7.47 (m, 1H), 7.38 (m, 1H), 7.36-7.18 (br t, 1H, CHF 2 ), 7.30 (m, 1H), 5.24 (s, 2H), 3.92 (s, 3H), 3.39 (s, 6H). Example No. A8-4:
1H-NMR (400 MHz, CDCIs δ, ppm) 7.71 (s, 1 H), 7.56 (m, 1 H), 7.52 (m, 1 H), 7.36-7.18 (br. t, 1 H, CHF2), 7.23 (m, 1 H), 5.31 (s, 2H), 3.92 (s, 3H), 3.39 (s, 6H). Beispiel No. A8-21 : 1 H-NMR (400 MHz, CDCIs δ, ppm) 7.71 (s, 1H), 7.56 (m, 1H), 7.52 (m, 1H), 7.36-7.18 (br.t, 1H, CHF 2 ), 7.23 (m, 1H), 5.31 (s, 2H), 3.92 (s, 3H), 3.39 (s, 6H). Example No. A8-21:
1H-NMR (400 MHz, CDCI3 δ, ppm) 8.63 (m, 1 H), 7.72 (m, 1 H), 7.68 (s, 1 H), 7.57 (m, 1 H), 7.34 (m, 1 H), 7.28-7.10 (br. t, 1 H, CHF2), 5.10 (s, 2H), 3.90 (s, 3H), 3.45 (s, 6H). 1 H-NMR (400 MHz, CDCl3 δ, ppm) 8.63 (m, 1H), 7.72 (m, 1H), 7.68 (s, 1H), 7.57 (m, 1H), 7.34 (m, 1 H), 7.28-7.10 (br t, 1H, CHF 2 ), 5.10 (s, 2H), 3.90 (s, 3H), 3.45 (s, 6H).
Beispiel No. A8-40: Example No. A8-40:
1H-NMR (400 MHz, CDCI3 δ, ppm) 8.47 (m, 1 H), 7.72 (s, 1 H), 7.52 (m, 1 H), 7.48-7.21 (br. t, 1 H, CHF2), 5.35 (s, 2H), 3.91 (s, 3H), 3.56 (s, 6H). 1H-NMR (400 MHz, CDCl 3 δ, ppm) 8:47 (m, 1 H), 7.72 (s, 1 H), 7:52 (m, 1 H), 7:48 to 7:21 (br. T, 1H, CHF 2) , 5.35 (s, 2H), 3.91 (s, 3H), 3.56 (s, 6H).
Beispiel No. A8-61 : Example No. A8-61:
1H-NMR (400 MHz, CDCI3 δ, ppm) 7.76-7.71 (m, 3H), 7.62 (m, 1 H), 7.55 (m, 1 H), 7.32- 7.13 (br. t, 1 H, CHF2), 5.30 (s, 2H), 3.92 (s, 3H), 3.43 (s, 6H). 1 H-NMR (400 MHz, CDCl3 δ, ppm) 7.76-7.71 (m, 3H), 7.62 (m, 1H), 7.55 (m, 1H), 7.32-7.13 (br.t, 1H, CHF 2 ), 5.30 (s, 2H), 3.92 (s, 3H), 3.43 (s, 6H).
Beispiel No. A15-21 : Example No. A15-21:
1H-NMR (400 MHz, CDCI3 δ, ppm) 8.58 (m, 1 H), 7.71 -7.67 (m, 1 H), 7.63-7.60 (m, 1 H), 7.28 (m, 1 H), 5.21 (s, 2H), 4.20-4.15 (m, 2H), 3.72 (s, 3H), 3.60-3.54 (m, 2H), 2.31 - 2.26 (m, 2H), 2.09-2.04 (m, 2H). 1 H-NMR (400 MHz, CDCl3 δ, ppm) 8.58 (m, 1H), 7.71-7.67 (m, 1H), 7.63-7.60 (m, 1H), 7.28 (m, 1H), 5.21 (s, 2H), 4.20-4.15 (m, 2H), 3.72 (s, 3H), 3.60-3.54 (m, 2H), 2.31-2.26 (m, 2H), 2.09-2.04 (m, 2H).
Beispiel No. A15-61 : Example No. A15-61:
1H-NMR (400 MHz, CDCI3 δ, ppm) 7.86 (m, 1 H), 7.72 (m, 2H), 7.64-7.59 (m, 1 H), 7.53- 7.49 (m, 1 H), 5.37 (s, 2H), 4.22-4.17 (m, 2H), 3.75 (s, 3H), 3.47-3.39 (m, 2H), 2.37- 2.29 (m, 2H), 2.16-2.09 (m, 2H). 1 H-NMR (400 MHz, CDCl3 δ, ppm) 7.86 (m, 1H), 7.72 (m, 2H), 7.64-7.59 (m, 1H), 7.53-7.49 (m, 1H), 5.37 ( s, 2H), 4.22-4.17 (m, 2H), 3.75 (s, 3H), 3.47-3.39 (m, 2H), 2.37-2.29 (m, 2H), 2.16-2.09 (m, 2H).
Beispiel No. A16-21 : Example No. A16-21:
1H-NMR (400 MHz, CDCI3 δ, ppm) 8.58 (m, 1 H), 7.70-7.65 (m, 2H), 7.62 (m, 1 H), 7.29 (m, 1 H), 5.21 (s, 2H), 4.20-4.15 (m, 2H), 3.72 (s, 3H), 3.60-3.54 (m, 2H), 2.32-2.25 (m, 2H), 2.09-2.03 (m, 2H). Beispiel No. A16-61 : 1 H-NMR (400 MHz, CDCl3 δ, ppm) 8.58 (m, 1H), 7.70-7.65 (m, 2H), 7.62 (m, 1H), 7.29 (m, 1H), 5.21 (s, 2H), 4.20-4.15 (m, 2H), 3.72 (s, 3H), 3.60-3.54 (m, 2H), 2.32-2.25 (m, 2H), 2.09-2.03 (m, 2H). Example No. A16-61:
1H-NMR (400 MHz, CDCIs δ, ppm) 7.78-7.75 (m, 1 H), 7.72-7.67 (m, 2H), 7.58-7.54 (m, 1 H), 7.51 -7.46 (m, 1 H), 5.37 (s, 2H), 4.23-4.16 (m, 2H), 3.74 (s, 3H), 3.48-3.42 (m, 2H), 2.31 -2.26 (m, 2H), 2.15-2.10 (m, 2H). 1 H-NMR (400 MHz, CDCls δ, ppm) 7.78-7.75 (m, 1H), 7.72-7.67 (m, 2H), 7.58-7.54 (m, 1H), 7.51-7.46 (m, 1H ), 5.37 (s, 2H), 4.23-4.16 (m, 2H), 3.74 (s, 3H), 3.48-3.42 (m, 2H), 2.31-2.26 (m, 2H), 2.15-2.10 (m, 2H ).
Beispiel No. A17-21 : Example No. A17-21:
1H-NMR (400 MHz, CDCI3 δ, ppm) 8.58 (m, 1 H), 7.68-7.63 (m, 2H), 7.57 (m, 1 H), 7.29 (m, 1 H), 5.22 (s, 2H), 4.17-4.12 (m, 2H), 3.86 (s, 3H), 3.66-3.59 (m, 2H), 2.31 -2.22 (m, 2H), 2.08-2.02 (m, 2H). 1 H-NMR (400 MHz, CDCl3 δ, ppm) 8.58 (m, 1H), 7.68-7.63 (m, 2H), 7.57 (m, 1H), 7.29 (m, 1H), 5.22 (s, 2H), 4.17-4.12 (m, 2H), 3.86 (s, 3H), 3.66-3.59 (m, 2H), 2.31-2.22 (m, 2H), 2.08-2.02 (m, 2H).
Beispiel No. A17-61 : Example No. A17-61:
1H-NMR (400 MHz, CDCI3 δ, ppm) 7.77 (m, 1 H), 7.71 (m, 2H), 7.59-7.55 (m, 1 H), 7.52- 7.48 (m, 1 H), 5.38 (s, 2H), 4.22-4.15 (m, 2H), 3.89 (s, 3H), 3.48-3.42 (m, 2H), 2.31 - 2.26 (m, 2H), 2.15-2.10 (m, 2H). 1 H-NMR (400 MHz, CDCl3 δ, ppm) 7.77 (m, 1H), 7.71 (m, 2H), 7.59-7.55 (m, 1H), 7.52-7.48 (m, 1H), 5.38 ( s, 2H), 4.22-4.15 (m, 2H), 3.89 (s, 3H), 3.48-3.42 (m, 2H), 2.31-2.26 (m, 2H), 2.15-2.10 (m, 2H).
Beispiel No. A18-61 : Example No. A18-61:
1H-NMR (400 MHz, CDCI3 δ, ppm) 7.78-7.76 (m, 1 H), 7.73-7.70 (m, 1 H), 7.61 -7.57 (m, 1 H), 7.53-7.49 (m, 1 H), 7.21 -6.94 (br. t, 1 H, CHF2), 5.39 (s, 2H), 4.23-4.18 (m, 2H), 3.87 (s, 3H), 3.49-3.42 (m, 2H), 2.38-2.28 (m, 2H), 2.18-2.1 1 (m, 2H). 1 H-NMR (400 MHz, CDCl3 δ, ppm) 7.78-7.76 (m, 1H), 7.73-7.70 (m, 1H), 7.61-7.57 (m, 1H), 7.53-7.49 (m, 1 H), 7.21-6.94 (br t, 1H, CHF 2 ), 5.39 (s, 2H), 4.23-4.18 (m, 2H), 3.87 (s, 3H), 3.49-3.42 (m, 2H), 2.38-2.28 (m, 2H), 2.18-2.1 1 (m, 2H).
Beispiel No. A19-61 : Example No. A19-61:
1H-NMR (400 MHz, CDCI3 δ, ppm) 7.7 (m, 1 H), 7.71 (m, 1 H), 7.61 (m, 1 H), 7.52 (m, 1 H), 7.19-6.92 (br. t, 1 H, CHF2), 5.37 (s, 2H), 4.18-4.1 1 (m, 2H), 3.88 (s, 3H), 3.51 - 3.43 (m, 2H), 2.35-2.28 (m, 2H), 2.19-2.10 (m, 2H). 1 H-NMR (400 MHz, CDCl3 δ, ppm) 7.7 (m, 1H), 7.71 (m, 1H), 7.61 (m, 1H), 7.52 (m, 1H), 7.19-6.92 (br t, 1H, CHF 2 ), 5.37 (s, 2H), 4.18-4.1 1 (m, 2H), 3.88 (s, 3H), 3.51 - 3.43 (m, 2H), 2.35-2.28 (m, 2H ), 2.19-2.10 (m, 2H).
Beispiel No. A20-61 : Example No. A20-61:
1H-NMR (400 MHz, CDCI3 δ, ppm) 7.74-7.66 (m, 3H), 7.58-7.48 (m, 2H), 7.31 -7.04 (br. t, 1 H, CHF2), 5.37 (s, 2H), 4.19-4.13 (m, 2H), 3.92 (s, 3H), 3.51 -3.44 (m, 2H), 2.31 - 2.24 (m, 2H), 2.16-2.08 (m, 2H). Beispiel No. A24-61 : 1 H NMR (400 MHz, CDCl 3 δ, ppm) 7.74-7.66 (m, 3H), 7.58-7.48 (m, 2H), 7.31 -7.04 (br t, 1H, CHF 2 ), 5.37 (s, 2H), 4.19-4.13 (m, 2H), 3.92 (s, 3H), 3.51-3.44 (m, 2H), 2.31-2.24 (m, 2H), 2.16-2.08 (m, 2H). Example No. A24-61:
1H-NMR (400 MHz, CDCI3 δ, ppm) 7.77 (m, 1 H), 7.72 (m, 1 H), 7.61 (m, 1 H), 7.52 (m, 1 H), 7.19-6.92 (br. t, 1 H, CHF2), 5.37 (s, 2H), 4.19-4.08 (m, 4H), 3.51 -3.43 (m, 2H), 2.35-2.28 (m, 2H), 2.19-2.10 (m, 2H), 1 .46 (t, 3H). Beispiel No. B3-4: 1 H-NMR (400 MHz, CDCl3 δ, ppm) 7.77 (m, 1H), 7.72 (m, 1H), 7.61 (m, 1H), 7.52 (m, 1H), 7.19-6.92 (br t, 1H, CHF 2 ), 5.37 (s, 2H), 4.19-4.08 (m, 4H), 3.51-3.43 (m, 2H), 2.35-2.28 (m, 2H), 2.19-2.10 (m, 2H), 1 .46 (t, 3H). Example No. B3-4:
1H-NMR (400 MHz, CDCIs δ, ppm) 7.68 (m, 1 H), 7.58 (m, 1 H), 7.49 (m, 1 H), 7.28 (m, 1H), 7.18 (m, 1H), 6.93-6.64 (br. t, 1H, CHF2), 5.20 (s, 2H), 3.46 (s, 6H). 1 H-NMR (400 MHz, CDCl3 δ, ppm) 7.68 (m, 1H), 7.58 (m, 1H), 7.49 (m, 1H), 7.28 (m, 1H), 7.18 (m, 1H) , 6.93-6.64 (br t, 1H, CHF 2 ), 5.20 (s, 2H), 3.46 (s, 6H).
Beispiel No. B3-40: Example No. B3-40:
1H-NMR (400 MHz, CDCI3 δ, ppm) 8.47 (d, 1H), 7.52-7.48 (m, 2H), 7.17 (m, 1H), 6.91- 6.63 (br. t, 1H, CHF2), 5.31 (s, 2H), 3.60 (s, 6H). Beispiel No. B3-61: 1 H-NMR (400 MHz, CDCl 3 δ, ppm) 8.47 (d, 1H), 7.52-7.48 (m, 2H), 7.17 (m, 1H), 6.91-6.63 (br.t, 1H, CHF 2 ), 5.31 (s, 2H), 3.60 (s, 6H). Example No. B3-61:
1H-NMR (400 MHz, CDCI3 δ, ppm) 8.64 (m, 1 H), 7.76-7.72 (m, 1 H), 7.67 (m, 1 H), 7.47 (m, 1H), 7.37 (m, 1H), 7.16 (m, 1H), 6.91-6.63 (br. t, 1H, CHF2), 5.03 (s, 2H), 3.48 (s, 6H). Beispiel No. B4-1: 1 H-NMR (400 MHz, CDCl 3 δ, ppm) 8.64 (m, 1H), 7.76-7.72 (m, 1H), 7.67 (m, 1H), 7.47 (m, 1H), 7.37 (m, 1H), 7.16 (m, 1H), 6.91-6.63 (br t, 1H, CHF 2 ), 5.03 (s, 2H), 3.48 (s, 6H). Example No. B4-1:
1H-NMR (400 MHz, CDCI3 δ, ppm) 7.71 (m, 1 H), 7.47 (m, 1 H), 7.37 (m, 1 H), 7.32 (m, 1H), 7.28 (m, 1H), 6.96 (m, 1H), 5.28 (s, 2H), 3.41 (s, 6H), 3.21 (q, 2H), 1.32 (t, 3H). 1 H-NMR (400 MHz, CDCl3 δ, ppm) 7.71 (m, 1H), 7.47 (m, 1H), 7.37 (m, 1H), 7.32 (m, 1H), 7.28 (m, 1H) , 6.96 (m, 1H), 5.28 (s, 2H), 3.41 (s, 6H), 3.21 (q, 2H), 1.32 (t, 3H).
Beispiel No. B4-21: Example No. B4-21:
1H-NMR (400 MHz, CDCI3 δ, ppm) 8.64 (m, 1 H), 7.73-7.70 (m, 1 H), 7.67-7.64 (m, 1 H), 7.36-7.31 (m, 1H), 7.18 (d, 1H), 6.93 (d, 1H), 5.15 (s, 2H), 3.47 (s, 6H), 3.10 (q, 2H), 1.27 (t, 3H). 1H-NMR (400 MHz, CDCl3 δ, ppm) 8.64 (m, 1H), 7.73-7.70 (m, 1H), 7.67-7.64 (m, 1H), 7.36-7.31 (m, 1H), 7.18 (d, 1H), 6.93 (d, 1H), 5.15 (s, 2H), 3.47 (s, 6H), 3.10 (q, 2H), 1.27 (t, 3H).
Beispiel No. B4-61: Example No. B4-61:
1H-NMR (400 MHz, CDCI3 δ, ppm) 8.64 (m, 1 H), 7.74-7.65 (m, 2H), 7.35-7.31 (m, 1 H), 7.18 (d, 1H), 6.92 (d, 1H), 5.15 (s, 2H), 3.47 (s, 6H), 3.11 (q, 2H), 1.25 (t, 3H). 1H-NMR (400 MHz, CDCl3 δ, ppm) 8.64 (m, 1H), 7.74-7.65 (m, 2H), 7.35-7.31 (m, 1H), 7.18 (d, 1H), 6.92 (d, 1H), 5.15 (s, 2H), 3.47 (s, 6H), 3.11 (q, 2H), 1.25 (t, 3H).
Beispiel No. B5-61: Example No. B5-61:
1H-NMR(400MHz, CDCI3 δ, ppm) 7.80 (m, 1H), 7.72 (m, 1H), 7.61-7.56 (m, 1H), 7.52- 7.48 (m, 1 H), 7.28 (m, 1 H), 6.96 (m, 1 H), 5.43 (s, 2H), 4.28-4.20 (m, 2H), 3.53-3.44 (m, 2H), 3.16 (q, 2H), 2.37-2.28 (m, 2H), 2.19-2.12 (m, 2H), 1.27 (t, 3H). Beispiel No. D1-1: 1 H-NMR (400MHz, CDCl3 δ, ppm) 7.80 (m, 1H), 7.72 (m, 1H), 7.61-7.56 (m, 1H), 7.52-7.48 (m, 1H), 7.28 (m, 1 H), 6.96 (m, 1H), 5.43 (s, 2H), 4.28-4.20 (m, 2H), 3.53-3.44 (m, 2H), 3.16 (q, 2H), 2.37-2.28 (m, 2H ), 2.19-2.12 (m, 2H), 1.27 (t, 3H). Example No. D1-1:
1H-NMR (400 MHz, CDCIs δ, ppm) 9.14 (m, 1 H), 8.63 (m, 1 H), 8.25 (m, 1 H), 7.72 (m, 1H), 7.49 (m, 1H), 7.42-7.31 (m, 3H), 5.19 (s, 2H), 3.45 (s, 6H), 2.78 (s, 3H). Beispiel No. D1-4: 1 H-NMR (400 MHz, CDCl3 δ, ppm) 9.14 (m, 1H), 8.63 (m, 1H), 8.25 (m, 1H), 7.72 (m, 1H), 7.49 (m, 1H) , 7.42-7.31 (m, 3H), 5.19 (s, 2H), 3.45 (s, 6H), 2.78 (s, 3H). Example No. D1-4:
1H-NMR(400MHz, CDCI3 δ, ppm) 9.13 (m, 1H), 8.63 (m, 1H), 8.24 (m, 1H), 7.66 (m, 1H), 7.58 (m, 1H), 7.37-7.34 (m, 1H), 7.31-7.28 (m, 1H), 5.25 (s, 2H), 3.46 (s, 6H), 2.78 (s, 3H). Beispiel No. D1 -35: 1 H-NMR (400MHz, CDCl3 δ, ppm) 9.13 (m, 1H), 8.63 (m, 1H), 8.24 (m, 1H), 7.66 (m, 1H), 7.58 (m, 1H), 7.37-7.34 (m, 1H), 7.31-7.28 (m, 1H), 5.25 (s, 2H), 3.46 (s, 6H), 2.78 (s, 3H). Example No. D1 -35:
1H-NMR(400MHz, CDCI3 δ, ppm) 9.12 (m, 1H), 8.62 (m, 1H), 8.56 (d, 1H), 8.24 (m, 1H), 7.87 (d, 1H), 7.37-7.33 (m, 1H), 5.23 (s, 2H), 3.57 (s, 6H), 2.77 (s, 3H). 1 H-NMR (400MHz, CDCl3 δ, ppm) 9.12 (m, 1H), 8.62 (m, 1H), 8.56 (d, 1H), 8.24 (m, 1H), 7.87 (d, 1H), 7.37-7.33 (m, 1H), 5.23 (s, 2H), 3.57 (s, 6H), 2.77 (s, 3H).
Beispiel No. D1-40: Example No. D1-40:
1H-NMR(400MHz, CDCI3 δ, ppm) 9.13 (m, 1H), 8.62 (m, 1H), 8.48 (d, 1H), 8.24 (m, 1H), 7.52 (d, 1H), 7.37-7.33 (m, 1H), 5.30 (s, 2H), 3.62 (s, 6H), 2.76 (s, 3H). 1H-NMR (400MHz, CDCl3 δ, ppm) 9.13 (m, 1H), 8.62 (m, 1H), 8.48 (d, 1H), 8.24 (m, 1H), 7.52 (d, 1H), 7.37-7.33 ( m, 1H), 5.30 (s, 2H), 3.62 (s, 6H), 2.76 (s, 3H).
Beispiel No. D1-61: Example No. D1-61:
1H-NMR (400 MHz, CDCI3 δ, ppm) 9.11 (m, 1 H), 8.66 (m, 1 H), 8.62 (m, 1 H), 8.23 (m, 1 H), 7.75-7.72 (m, 1 H), 7.66 (m, 1 H), 7.37-7.32 (m, 2H), 5.08 (s, 2H), 3.50 (s, 6H), 2.74 (s, 3H). 1 H-NMR (400 MHz, CDCl3 δ, ppm) 9.11 (m, 1H), 8.66 (m, 1H), 8.62 (m, 1H), 8.23 (m, 1H), 7.75-7.72 (m , 1H), 7.66 (m, 1H), 7.37-7.32 (m, 2H), 5.08 (s, 2H), 3.50 (s, 6H), 2.74 (s, 3H).
Beispiel No. D1-94: Example No. D1-94:
1H-NMR(400MHz, CDCI3 δ, ppm) 9.13 (m, 1H), 8.64 (m, 1H), 8.47 (m, 1H), 8.23 (m, 1 H), 7.90-7.86 (m, 1 H), 7.41 (m, 1 H), 7.36 (m, 1 H), 4.93 (s, 2H), 3.44 (s, 6H), 2.76 (s, 3H). 1 H-NMR (400MHz, CDCl3 δ, ppm) 9.13 (m, 1H), 8.64 (m, 1H), 8.47 (m, 1H), 8.23 (m, 1H), 7.90-7.86 (m, 1H) , 7.41 (m, 1H), 7.36 (m, 1H), 4.93 (s, 2H), 3.44 (s, 6H), 2.76 (s, 3H).
Beispiel No. D2-21: Example No. D2-21:
1H-NMR (400 MHz, CDCI3 δ, ppm) 9.11 (m, 1 H), 8.61 (m, 2H), 8.21 (m, 1 H), 7.70-7.66 (m, 1 H), 7.54 (m, 1 H), 7.35-7.31 (m, 2H), 5.21 (s, 2H), 4.20-4.13 (m, 2H), 3.77-3.68 (m, 2H), 2.71 (s, 3H), 2.33-2.25 (m, 2H), 2.14-2.08 (m, 2H). Beispiel No. D2-61 : 1 H-NMR (400 MHz, CDCl3 δ, ppm) 9.11 (m, 1H), 8.61 (m, 2H), 8.21 (m, 1H), 7.70-7.66 (m, 1H), 7.54 (m, 1 H), 7.35-7.31 (m, 2H), 5.21 (s, 2H), 4.20-4.13 (m, 2H), 3.77-3.68 (m, 2H), 2.71 (s, 3H), 2.33-2.25 (m , 2H), 2.14-2.08 (m, 2H). Example No. D2-61:
1H-NMR (400 MHz, CDCIs δ, ppm) 9.12 (m, 1 H), 8.63 (m, 2H), 8.23 (m, 1 H), 7.75-7.71 (m, 2H), 7.61 (m, 1 H), 7.53 (m, 1 H), 7.36 (m, 1 H), 5.38 (s, 2H), 4.25-4.18 (m, 2H), 3.54-3.48 (m, 2H), 2.76 (s, 3H), 2.35-2.28 (m, 2H), 2.20-2.13 (m, 2H). 1 H-NMR (400 MHz, CDCIs δ, ppm) 9.12 (m, 1H), 8.63 (m, 2H), 8.23 (m, 1H), 7.75-7.71 (m, 2H), 7.61 (m, 1 H), 7.53 (m, 1H), 7.36 (m, 1H), 5.38 (s, 2H), 4.25-4.18 (m, 2H), 3.54-3.48 (m, 2H), 2.76 (s, 3H) , 2.35-2.28 (m, 2H), 2.20-2.13 (m, 2H).
Beispiel No. D6-1 : Example No. D6-1:
1H-NMR (400 MHz, CDCI3 δ, ppm) 7.70 (m, 1 H), 7.49 (m, 1 H), 7.43-7.35 (m, 1 H), 5.07 (s, 2H), 3.42 (s, 6H). 1 H-NMR (400 MHz, CDCl3 δ, ppm) 7.70 (m, 1H), 7.49 (m, 1H), 7.43-7.35 (m, 1H), 5.07 (s, 2H), 3.42 (s, 6H).
Beispiel No. D6-3: Example No. D6-3:
1H-NMR (400 MHz, CDCI3 δ, ppm) 7.42 (m, 4H), 4.81 (s, 2H), 3.35 (s, 6H). Beispiel No. D6-1 1 : 1 H-NMR (400 MHz, CDCl 3 δ, ppm) 7.42 (m, 4H), 4.81 (s, 2H), 3.35 (s, 6H). Example No. D6-1 1:
1H-NMR (400 MHz, CDCI3 δ, ppm) 7.59-7.55 (m, 1 H), 7.50-7.45 (m, 1 H), 7.25-7.21 (m, 1 H), 7.19-7.14 (m, 1 H), 4.93 (s, 2H), 3.39 (s, 6H). 1H-NMR (400 MHz, CDCl3 δ, ppm) 7.59-7.55 (m, 1H), 7.50-7.45 (m, 1H), 7.25-7.21 (m, 1H), 7.19-7.14 (m, 1H ), 4.93 (s, 2H), 3.39 (s, 6H).
Beispiel No. D6-15: Example No. D6-15:
1H-NMR (400 MHz, CDCI3 δ, ppm) 7.63-7.57 (m, 1 H), 6.99-6.89 (m, 2H), 4.89 (s, 2H), 3.39 (s, 6H). 1 H-NMR (400 MHz, CDCl3 δ, ppm) 7.63-7.57 (m, 1H), 6.99-6.89 (m, 2H), 4.89 (s, 2H), 3.39 (s, 6H).
Beispiel No. E1 -1 : Example No. E1 -1:
1H-NMR (400 MHz, CDCI3 δ, ppm) 7.73 (m, 1 H), 7.50 (m, 1 H), 7.42 (m, 1 H), 7.35 (m, 1 H), 5.08 (s, 2H), 3.45 (s, 6H). 1 H-NMR (400 MHz, CDCl3 δ, ppm) 7.73 (m, 1H), 7.50 (m, 1H), 7.42 (m, 1H), 7.35 (m, 1H), 5.08 (s, 2H ), 3.45 (s, 6H).
Beispiel No. E1 -3: Example No. E1 -3:
1H-NMR (400 MHz, CDCI3 δ, ppm) 7.45 (d, 2H), 7.42 (d, 2H), 4.83 (s, 2H), 3.38 (s, 6H). Beispiel No. E1 -4: 1 H-NMR (400 MHz, CDCl3 δ, ppm) 7.45 (d, 2H), 7.42 (d, 2H), 4.83 (s, 2H), 3.38 (s, 6H). Example No. E1 -4:
1H-NMR (400 MHz, CDCI3 δ, ppm) 7.67 (m, 1 H), 7.61 (m, 1 H), 7.30 (m, 1 H), 5.14 (s, 2H), 3.47 (s, 6H). Beispiel No. E1 -21 : 1H-NMR (400 MHz, CDCl3 δ, ppm) 7.67 (m, 1H), 7.61 (m, 1H), 7.30 (m, 1H), 5.14 (s, 2H), 3.47 (s, 6H). Example No. E1 -21:
1H-NMR (400 MHz, CDCIs δ, ppm) 8.65 (m, 1 H), 7.77-7.73 (m, 1 H), 7.67-7.64 (m, 1 H), 7.39-7.36 (m, 1 H), 4.98 (s, 2H), 3.49 (s, 6H). 1 H-NMR (400 MHz, CDCls δ, ppm) 8.65 (m, 1H), 7.77-7.73 (m, 1H), 7.67-7.64 (m, 1H), 7.39-7.36 (m, 1H) , 4.98 (s, 2H), 3.49 (s, 6H).
Beispiel No. E1 -35: Example No. E1 -35:
1H-NMR (400 MHz, CDCI3 δ, ppm) 8.55 (m, 1 H), 7.87 (m, 1 H), 5.13 (s, 2H), 3.58 (s, 6H). Beispiel No. E1 -61 : 1 H-NMR (400 MHz, CDCl3 δ, ppm) 8.55 (m, 1H), 7.87 (m, 1H), 5.13 (s, 2H), 3.58 (s, 6H). Example No. E1 -61:
1H-NMR (400 MHz, CDCI3 δ, ppm) 7.89 (m, 1 H), 7.78 (m, 1 H), 7.69 (m, 1 H), 7.60 (m, 1 H), 5.10 (s, 2H), 3.51 (s, 6H). 1 H-NMR (400 MHz, CDCl3 δ, ppm) 7.89 (m, 1H), 7.78 (m, 1H), 7.69 (m, 1H), 7.60 (m, 1H), 5.10 (s, 2H ), 3.51 (s, 6H).
Beispiel No. E1 -94: Example No. E1 -94:
1H-NMR (400 MHz, CDCI3 δ, ppm) 8.46 (m, 1 H), 7.92 (m, 1 H), 7.43 (m, 1 H), 4.83 (s, 2H), 3.45 (s, 6H). 1H-NMR (400 MHz, CDCl3 δ, ppm) 8.46 (m, 1H), 7.92 (m, 1H), 7.43 (m, 1H), 4.83 (s, 2H), 3.45 (s, 6H).
Beispiel No. E1 -351 : Example No. E1 -351:
1H-NMR (400 MHz, CDCI3 δ, ppm) 7.53 (m, 2H), 7.48-7.44 (m, 3H), 4.98 (m, 1 H), 3.43 (s, 3H), 3.22 (s, 3H), 2.60-2.53 (m, 1 H), 2.30-2.20 (m, 1 H), 0.78 (m, 3H). 1 H-NMR (400 MHz, CDCl3 δ, ppm) 7.53 (m, 2H), 7.48-7.44 (m, 3H), 4.98 (m, 1H), 3.43 (s, 3H), 3.22 (s, 3H) , 2.60-2.53 (m, 1H), 2.30-2.20 (m, 1H), 0.78 (m, 3H).
Beispiel No. E1 -454: Example No. E1 -454:
1H-NMR (400 MHz, CDCI3 δ, ppm) 7.30 (m, 2H), 7.13 (d, 2H), 3.64-3.58 (m, 2H), 3.41 (s, 6H), 2.72-2.68 (m, 2H), 2.18-2.15 (m, 2H). 1 H-NMR (400 MHz, CDCl 3 δ, ppm) 7.30 (m, 2H), 7.13 (d, 2H), 3.64-3.58 (m, 2H), 3.41 (s, 6H), 2.72-2.68 (m, 2H ), 2.18-2.15 (m, 2H).
Beispiel No. E1 -612: Example No. E1 -612:
1H-NMR (400 MHz, CDCI3 δ, ppm) 7.38 (m, 1 H), 7.31 (m, 1 H), 7.27-7.22 (m, 2H), 3.83- 3.79 (m, 2H), 3.53 (s, 6H), 3.32-3.28 (m, 2H). Beispiel No. E2-13: 1 H-NMR (400 MHz, CDCl3 δ, ppm) 7.38 (m, 1H), 7.31 (m, 1H), 7.27-7.22 (m, 2H), 3.83- 3.79 (m, 2H), 3.53 (s , 6H), 3.32-3.28 (m, 2H). Example No. E2-13:
1H-NMR (400 MHz, CDCI3 δ, ppm) 7.49 (m, 2H), 7.03 (m, 2H), 4.64 (s, 2H), 3.02-2.95 (m, 2H), 2.89-2.83 (m, 2H), 0.92 (t, 6H). Beispiel No. E2-61 : 1 H-NMR (400 MHz, CDCl3 δ, ppm) 7.49 (m, 2H), 7.03 (m, 2H), 4.64 (s, 2H), 3.02-2.95 (m, 2H), 2.89-2.83 (m, 2H ), 0.92 (t, 6H). Example No. E2-61:
1H-NMR (400 MHz, CDCIs δ, ppm) 7.86 (m, 1 H), 7.75 (m, 1 H), 7.63-7.60 (m, 1 H), 7.57- 7.52 (m, 1 H), 5.21 (s, 2H), 4.03-3.98 (m, 2H), 3.62-3.57 (m, 2H), 1 .40 (t, 6H). 1 H-NMR (400 MHz, CDCl3 δ, ppm) 7.86 (m, 1H), 7.75 (m, 1H), 7.63-7.60 (m, 1H), 7.57-7.52 (m, 1H), 5.21 (s, 2H), 4.03-3.98 (m, 2H), 3.62-3.57 (m, 2H), 1.40 (t, 6H).
Beispiel No. E3-21 : Example No. E3-21:
1H-NMR (400 MHz, CDCI3 δ, ppm) 8.55 (m, 1 H), 7.72-7.66 (m, 1 H), 7.54 (m, 1 H), 7.22 (m, 1 H), 5.23 (d, 1 H), 4.67 (d, 1 H), 3.10 (s, 3H), 1 .36 (s, 9H). Beispiel No. E4-21 : 1 H-NMR (400 MHz, CDCl3 δ, ppm) 8.55 (m, 1H), 7.72-7.66 (m, 1H), 7.54 (m, 1H), 7.22 (m, 1H), 5.23 (i.e. , 1H), 4.67 (d, 1H), 3.10 (s, 3H), 1 .36 (s, 9H). Example No. E4-21:
1H-NMR (400 MHz, CDCI3 δ, ppm) 8.52 (m, 1 H), 7.73-7.68 (m, 1 H), 7.40 (m, 1 H), 7.25- 7.22 (m, 1 H), 5.49 (m, 1 H), 5.24-4.58 (m, 2H), 2.78 (d, 3H). 1 H-NMR (400 MHz, CDCl3 δ, ppm) 8.52 (m, 1H), 7.73-7.68 (m, 1H), 7.40 (m, 1H), 7.25- 7.22 (m, 1H), 5.49 (m, 1H), 5.24-4.58 (m, 2H), 2.78 (d, 3H).
Beispiel No. E5-61 : Example No. E5-61:
1H-NMR (400 MHz, CDCI3 δ, ppm) 7.76-7.70 (m, 2H), 7.64-7.60 (m, 1 H), 7.57-7.52 (m, 1 H), 5.33 (s, 2H), 4.23-4.17 (m, 2H), 3.53-3.47 (m, 2H), 2.33-2.28 (m, 2H), 2.19-2.15 (m, 2H). 1H-NMR (400 MHz, CDCl3 δ, ppm) 7.76-7.70 (m, 2H), 7.64-7.60 (m, 1H), 7.57-7.52 (m, 1H), 5.33 (s, 2H), 4.23- 4.17 (m, 2H), 3.53-3.47 (m, 2H), 2.33-2.28 (m, 2H), 2.19-2.15 (m, 2H).
Beispiel No. F1 -1 : Example No. F1 -1:
1H-NMR (400 MHz, CDCI3 δ, ppm) 7.67-7.63 (m, 1 H), 7.48 (m, 1 H), 7.42 (m, 1 H), 7.34 (m, 1 H), 5.10 (s, 2H), 3.44 (s, 6H), 2.93 (s, 3H). 1H-NMR (400 MHz, CDCl3 δ, ppm) 7.67-7.63 (m, 1H), 7.48 (m, 1H), 7.42 (m, 1H), 7.34 (m, 1H), 5.10 (s, 2H), 3.44 (s, 6H), 2.93 (s, 3H).
Beispiel No. F1 -4: Example No. F1 -4:
1H-NMR (400 MHz, CDCI3 δ, ppm) 7.60 (m, 2H), 7.29 (m, 1 H), 5.16 (s, 2H), 3.45 (s, 6H), 2.92 (s, 3H). 1 H-NMR (400 MHz, CDCl3 δ, ppm) 7.60 (m, 2H), 7.29 (m, 1H), 5.16 (s, 2H), 3.45 (s, 6H), 2.92 (s, 3H).
Beispiel No. F1 -21 : Example No. F1 -21:
1H-NMR (400 MHz, CDCI3 δ, ppm) 8.66 (m, 1 H), 7.75-7.72 (m, 1 H), 7.60 (m, 1 H), 7.39- 7.35 (m, 1 H), 5.00 (s, 2H), 3.49 (s, 6H), 2.89 (s, 3H). 1 H-NMR (400 MHz, CDCl3 δ, ppm) 8.66 (m, 1H), 7.75-7.72 (m, 1H), 7.60 (m, 1H), 7.39-7.35 (m, 1H), 5.00 (s, 2H), 3.49 (s, 6H), 2.89 (s, 3H).
Beispiel No. F1 -35: Example No. F1 -35:
1H-NMR (400 MHz, CDCI3 δ, ppm) 8.55 (m, 1 H), 7.87 (m, 1 H), 5.14 (s, 2H), 3.56 (s, 6H), 2.91 (s, 3H). Beispiel No. F1 -40: 1 H-NMR (400 MHz, CDCl3 δ, ppm) 8.55 (m, 1H), 7.87 (m, 1H), 5.14 (s, 2H), 3.56 (s, 6H), 2.91 (s, 3H). Example No. F1 -40:
1H-NMR (400 MHz, CDCIs δ, ppm) 8.47 (d, 1 H), 7.53 (d, 1 H), 5.23 (s, 2H), 3.60 (s, 6H), 2.91 (s, 3H). 1 H-NMR (400 MHz, CDCls δ, ppm) 8.47 (d, 1H), 7.53 (d, 1H), 5.23 (s, 2H), 3.60 (s, 6H), 2.91 (s, 3H).
Beispiel No. F1 -61 : Example No. F1 -61:
1H-NMR (400 MHz, CDCI3 δ, ppm) 7.80-7.77 (m, 2H), 7.67-7.64 (m, 1 H), 7.62-7.59 (m, 1 H), 5.12 (s, 2H), 3.50 (s, 6H), 2.92 (s, 3H). Beispiel No. F1 -94: 1 H-NMR (400 MHz, CDCl3 δ, ppm) 7.80-7.77 (m, 2H), 7.67-7.64 (m, 1H), 7.62-7.59 (m, 1H), 5.12 (s, 2H), 3.50 (s, 6H), 2.92 (s, 3H). Example No. F1 -94:
1H-NMR (400 MHz, CDCI3 δ, ppm) 8.45 (m, 1 H), 7.85 (m, 1 H), 7.42 (m, 1 H), 4.85 (s, 2H), 3.43 (s, 6H), 2.91 (s, 3H). 1 H-NMR (400 MHz, CDCl3 δ, ppm) 8.45 (m, 1H), 7.85 (m, 1H), 7.42 (m, 1H), 4.85 (s, 2H), 3.43 (s, 6H) , 2.91 (s, 3H).
Beispiel No. F2-4: Example No. F2-4:
1H-NMR (400 MHz, CDCI3 δ, ppm) 7.60 (m, 2H), 7.28 (m, 1 H), 5.16 (s, 2H), 4.1 1 -4.05 (m, 1 H), 3.45 (s, 6H), 1 .48 (d, 6H). 1 H NMR (400 MHz, CDCl 3 δ, ppm) 7.60 (m, 2H), 7.28 (m, 1H), 5.16 (s, 2H), 4.1 1 -4.05 (m, 1H), 3.45 (s, 6H ), 1 .48 (d, 6H).
Beispiel No. F2-21 : Example No. F2-21:
1H-NMR (400 MHz, CDCI3 δ, ppm) 8.66 (m, 1 H), 7.75-7.71 (m, 1 H), 7.61 (m, 1 H), 7.39- 7.36 (m, 1 H), 5.00 (s, 2H), 4.06-4.00 (m, 1 H), 3.49 (s, 6H), 1 .46 (d, 6H). 1 H-NMR (400 MHz, CDCl3 δ, ppm) 8.66 (m, 1H), 7.75-7.71 (m, 1H), 7.61 (m, 1H), 7.39-7.36 (m, 1H), 5.00 (s, 2H), 4.06-4.00 (m, 1H), 3.49 (s, 6H), 1 .46 (d, 6H).
Beispiel No. F2-35: Example No. F2-35:
1H-NMR (400 MHz, CDCI3 δ, ppm) 8.55 (d, 1 H), 7.87 (d, 1 H), 5.13 (s, 2H), 4.08-4.03 (sept, 1 H), 3.57 (s, 6H), 1 .47 (d, 6H). 1 H-NMR (400 MHz, CDCl3 δ, ppm) 8.55 (d, 1H), 7.87 (d, 1H), 5.13 (s, 2H), 4.08-4.03 (sept, 1H), 3.57 (s, 6H), 1 .47 (d, 6H).
Beispiel No. F2-40: Example No. F2-40:
1H-NMR (400 MHz, CDCI3 δ, ppm) 8.47 (d, 1 H), 7.52 (d, 1 H), 5.22 (s, 2H), 4.08-4.03 (sept, 1 H), 3.61 (s, 6H), 1 .47 (d, 6H). Beispiel No. F2-94: 1 H-NMR (400 MHz, CDCl3 δ, ppm) 8.47 (d, 1H), 7.52 (d, 1H), 5.22 (s, 2H), 4.08-4.03 (sept, 1H), 3.61 (s, 6H), 1 .47 (d, 6H). Example No. F2-94:
1H-NMR (400 MHz, CDCI3 δ, ppm) 8.44 (m, 1 H), 7.85 (m, 1 H), 7.41 (m, 1 H), 4.85 (s, 2H), 4.08-4.03 (m, 1 H), 3.43 (s, 6H), 1 .48 (d, 6H). Beispiel No. H1 -1 : 1 H-NMR (400 MHz, CDCl3 δ, ppm) 8.44 (m, 1H), 7.85 (m, 1H), 7.41 (m, 1H), 4.85 (s, 2H), 4.08-4.03 (m, 1 H), 3.43 (s, 6H), 1 .48 (d, 6H). Example No. H1 -1:
1H-NMR (400 MHz, CDCIs δ, ppm) 8.97 (s, 1 H), 7.67 (m, 1 H), 7.50 (m, 1 H), 7.41 (m, 1 H), 7.32 (m, 1 H), 5.29 (s, 2H), 3.49 (s, 6H). 1 H-NMR (400 MHz, CDCl3 δ, ppm) 8.97 (s, 1H), 7.67 (m, 1H), 7.50 (m, 1H), 7.41 (m, 1H), 7.32 (m, 1 H), 5.29 (s, 2H), 3.49 (s, 6H).
Beispiel No. H1 -3: Example No. H1 -3:
1H-NMR (400 MHz, CDCI3 δ, ppm) 8.94 (s, 1 H), 7.45-7.39 (m, 4H), 5.02 (s, 2H), 3.42 (s, 6H). Beispiel No. H1 -4: 1 H-NMR (400 MHz, CDCl3 δ, ppm) 8.94 (s, 1H), 7.45-7.39 (m, 4H), 5.02 (s, 2H), 3.42 (s, 6H). Example No. H1 -4:
1H-NMR (400 MHz, CDCI3 δ, ppm) 8.96 (s, 1 H), 7.62-7.55 (m, 2H), 7.25 (m, 1 H), 5.35 (s, 2H), 3.50 (s, 6H). 1 H-NMR (400 MHz, CDCl3 δ, ppm) 8.96 (s, 1H), 7.62-7.55 (m, 2H), 7.25 (m, 1H), 5.35 (s, 2H), 3.50 (s, 6H ).
Beispiel No. H1 -1 1 : Example No. H1 -1 1:
1H-NMR (400 MHz, CDCI3 δ, ppm) 8.96 (s, 1 H), 7.57-7.53 (m, 1 H), 7.48-7.44 (m, 1 H), 7.22-7.15 (m, 2H), 5.15 (s, 2H), 3.46 (s, 6H). 1H-NMR (400 MHz, CDCl3 δ, ppm) 8.96 (s, 1H), 7.57-7.53 (m, 1H), 7.48-7.44 (m, 1H), 7.22-7.15 (m, 2H), 5.15 (s, 2H), 3.46 (s, 6H).
Beispiel No. H1 -15: Example No. H1 -15:
1H-NMR (400 MHz, CDCI3 δ, ppm) 8.94 (s, 1 H), 7.59-7.54 (m, 1 H), 6.95-6.90 (m, 2H), 5.1 1 (s, 2H), 3.45 (s, 6H). 1 H-NMR (400 MHz, CDCl3 δ, ppm) 8.94 (s, 1H), 7.59-7.54 (m, 1H), 6.95-6.90 (m, 2H), 5.1 1 (s, 2H), 3.45 ( s, 6H).
Beispiel No. H1 -61 : Example No. H1 -61:
1H-NMR (400 MHz, CDCI3 δ, ppm) 8.95 (s, 1 H), 7.82-7.76 (m, 2H), 7.65-7.61 (m, 1 H), 7.59-7.54 (m, 1 H), 5.32 (s, 2H), 3.54 (s, 6H). b) NMR-Peak-Listenverfahren: 1 H-NMR (400 MHz, CDCl3 δ, ppm) 8.95 (s, 1H), 7.82-7.76 (m, 2H), 7.65-7.61 (m, 1H), 7.59-7.54 (m, 1H), 5.32 (s, 2H), 3.54 (s, 6H). b) NMR peak list method:
Die 1H-NMR-Daten ausgewählter Beispiele werden in Form von 1H-NMR-Peaklisten notiert. Zu jedem Signalpeak wird erst der δ-Wert in ppm und dann die Signalintensität in runden Klammern aufgeführt. Die δ-Wert - Signalintensitäts- Zahlenpaare von verschiedenen Signalpeaks werden durch Semikolons voneinander getrennt aufgelistet. Die Peakliste eines entsprechenden Beispieles hat daher die Form: δι (Intensität^; δ2 (lntensität.2); ; δ, (Intensität,); ; δη (Intensität) Die Intensität scharfer Signale korreliert mit der Höhe der Signale in einem gedruckten Beispiel eines NMR-Spektrums in cm und zeigt die wirklichen Verhältnisse der The 1 H NMR data of selected examples are noted in terms of 1 H NMR peaks. For each signal peak, first the δ value in ppm and then the signal intensity in round brackets are listed. The δ-value signal intensity number pairs of different signal peaks are listed separated by semicolons. The peak list of a corresponding example therefore has the form: δι (intensity ^; δ2 (intensity.2);; δ, (intensity, ) ;; δ η (intensity); The intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the
Signalintensitäten. Bei breiten Signalen können mehrere Peaks oder die Mitte des Signals und ihre relative Intensität im Vergleich zum intensivsten Signal im Spektrum gezeigt werden. Zur Kalibrierung der chemischen Verschiebung von 1H-NMR-Spektren benutzten wir Tetramethylsilan und/oder die chemische Verschiebung des Signal intensities. For broad signals, multiple peaks or the center of the signal and their relative intensity can be shown compared to the most intense signal in the spectrum. To calibrate the chemical shift of 1 H NMR spectra, we used tetramethylsilane and / or the chemical shift of the
Lösungsmittels, besonders im Falle von Spektren, die in DMSO gemessen werden. Daher kann in NMR-Peaklisten der Tetramethylsilan-Peak vorkommen, muss es aber nicht. Die Listen der 1H-NMR-Peaks sind ähnlich den klassischen 1H-NMR-Ausdrucken und enthalten somit gewöhnlich alle Peaks, die bei einer klassischen NMR-Solvent, especially in the case of spectra measured in DMSO. Therefore, the tetramethylsilane peak can occur in NMR peaks, but it does not have to. The lists of the 1 H NMR peaks are similar to the classical 1 H NMR prints and thus usually contain all the peaks which are present in a classical NMR
Interpretation aufgeführt werden. Darüber hinaus können sie wie klassische 1H-NMR- Ausdrucke Lösungsmittelsignale, Signale von Stereoisomeren der Zielverbindungen, die ebenfalls Gegenstand der Erfindung sind, und/oder Peaks von Verunreinigungen zeigen. Bei der Angabe von Verbindungssignalen im Delta-Bereich von Lösungsmitteln und/oder Wasser sind in unseren Listen von 1H-NMR-Peaks die gewöhnlichen Interpretation are listed. In addition, like classical 1 H NMR prints, they can show solvent signals, signals from stereoisomers of the target compounds, which are also the subject of the invention, and / or peaks of impurities. When specifying connection signals in the delta range of solvents and / or water are the usual in our lists of 1 H NMR peaks
Lösungsmittelpeaks, zum Beispiel Peaks von DMSO in DMSO-d6 und der Peak von Wasser, gezeigt, die gewöhnlich im Durchschnitt eine hohe Intensität aufweisen. Die Peaks von Stereoisomeren der Targetverbindungen und/oder Peaks von  Solvent peaks, for example peaks of DMSO in DMSO-d6 and the peak of water, which are usually of high intensity on average. The peaks of stereoisomers of the target compounds and / or peaks of
Verunreinigungen haben gewöhnlich im Durchschnitt eine geringere Intensität als die Peaks der Zielverbindungen (zum Beispiel mit einer Reinheit von >90%). Solche Stereoisomere und/oder Verunreinigungen können typisch für das jeweilige Impurities usually have on average a lower intensity than the peaks of the target compounds (for example with a purity of> 90%). Such stereoisomers and / or impurities may be typical of each
Herstellungsverfahren sein. Ihre Peaks können somit dabei helfen, die Reproduktion unseres Herstellungsverfahrens anhand von "Nebenprodukt-Fingerabdrücken" zu erkennen. Be manufacturing process. Their peaks can thus help identify the reproduction of our manufacturing process by "by-product fingerprints."
Einem Experten, der die Peaks der Zielverbindungen mit bekannten Verfahren An expert who analyzes the peaks of the target compounds using known methods
(MestreC, ACD-Simulation, aber auch mit empirisch ausgewerteten Erwartungswerten) berechnet, kann je nach Bedarf die Peaks der Zielverbindungen isolieren, wobei gegebenenfalls zusätzliche Intensitätsfilter eingesetzt werden. Diese Isolierung wäre ähnlich dem betreffenden Peak-Picking bei der klassischen 1H-NMR-lnterpretation. (MestreC, ACD simulation, but also with empirically evaluated expected values), can isolate the peaks of the target compounds as needed, using additional intensity filters if necessary. This isolation would be similar to peak-picking in the classical 1 H NMR interpretation.
Beispiel No. A1 -1 : 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. A1 -1: 1 H-NMR (400 MHz, CDCls δ, ppm)
7,782(0,9);7,777(0,9);7,763(1 ,0);7,758(1 ,0);7,474(0,7);7,471 (0,9);7,454(1 ,1 );7,451 (1 ,3) ;7,402(0,5);7,398(0,6);7,384(1 ,1 );7,379(1 ,0);7,364(0,7);7,359(0,6);7,345(0,8);7,341 (0,8 );7,326(1 ,1 );7,323(1 ,1 );7,262(29,2);5,300(0,8);5,243(5,0);3,860(8,2);3,391 (16,0);1 ,584( 2,4);0,000(8,2) 7,782 (0.9); 7,777 (0.9); 7,763 (1, 0); 7,758 (1, 0); 7,474 (0.7); 7,471 (0.9); 7,454 (1, 1); 7,451 (1, 3); 7,402 (0.5); 7,398 (0.6); 7,384 (1,1); 7,379 (1, 0); 7,364 (0.7); 7,359 (0,6); 7,345 ( 0.8), 7.341 (0.8 7,326 (1, 1), 7,323 (1,1), 7,262 (29,2), 5,300 (0,8), 5,243 (5,0), 3,860 (8,2), 3,391 (16,0) ; 1, 584 (2,4); 0,000 (8,2)
Beispiel No. A1 -15: 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. A1 -15: 1 H-NMR (400 MHz, CDCIs δ, ppm)
8,941 (6,9);7,586(0,5);7,579(0,9);7,563(0,9);7,559(0,6);7,543(0,5);7,270(13,2);6,954(0, 7);6,949(0,7);6,942(0,9);6,934(1 ,3);6,928(0,8);6,922(1 ,3);6,917(1 ,1 );6,902(0,7);5,303(6 ,9);5,1 14(4,5);3,455(15,4);3,452(16,0);2,047(0,6);1 ,709(0,7);0,000(5,0) 8.941 (6.9); 7.586 (0.5); 7.579 (0.9); 7.563 (0.9); 7.559 (0.6); 7.543 (0.5); 7.270 (13.2); 6.954 (0, 7), 6.949 (0.7), 6.942 (0.9), 6.934 (1.3), 6.928 (0.8), 6.922 (1.3), 6.917 (1, 1), 6.902 ( 5.7), 5.303 (6, 9), 5.1 14 (4.5), 3.455 (15.4), 3.452 (16.0), 2.047 (0.6), 1.709 (0.7 ); 0,000 (5.0)
Beispiel No. A1 -21 : 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. A1 -21: 1 H-NMR (400 MHz, CDCIs δ, ppm)
8,637(1 ,0);8,635(1 ,2);8,633(1 ,3);8,630(1 ,1 );8,625(1 ,1 );8,621 (1 ,5);8,618(1 ,0);7,739(1 ,4) ;7,735(1 ,5);7,722(3,2);7,718(3,6);7,715(2,0);7,520(0,6);7,354(1 ,0);7,349(1 ,0);7,342(1 ,0 );7,337(1 ,7);7,332(0,9);7,325(0,8);7,320(0,9);7,261 (98,6);6,997(0,6);5,125(6,5);3,834(1 3,2);3,458(16,0);2,045(1 ,9);1 ,574(1 ,4);1 ,259(1 ,0);0,008(0,9);0,000(29,8);-0,009(0,8) Beispiel No. A1 -37: 1H-NMR (400 MHz, CDCIs δ, ppm) 8.637 (1, 0), 8.635 (1, 2), 8.633 (1, 3), 8.630 (1, 1), 8.625 (1, 1), 8.621 (1, 5), 8.618 (1, 0), 7.739 (1, 4); 7,735 (1, 5); 7,722 (3,2); 7,718 (3,6); 7,715 (2,0); 7,520 (0,6); 7,354 (1, 0); 7,349 ( 1, 0), 7.322 (1, 0), 7.337 (1, 7), 7.332 (0.9), 7.325 (0.8), 7.320 (0.9), 7.261 (98.6), 6.997 (0 , 6); 5,125 (6,5); 3,834 (1 3,2); 3,458 (16,0); 2,045 (1, 9); 1, 574 (1, 4); 1, 259 (1, 0) 0.008 (0.9); 0.000 (29.8); 0.009 (0.8) Example no. A1 -37: 1 H-NMR (400 MHz, CDCIs δ, ppm)
8,289(1 ,8);7,262(60,2);5,127(2,5);3,853(6,9);3,789(16,0);3,466(7,5);2,460(8,4);2,300(6 ,6);0,008(0,5);0,000(16,2)  8.289 (1, 8); 7.262 (60.2); 5.127 (2.5); 3.853 (6.9); 3.789 (16.0); 3.466 (7.5); 2.460 (8.4); 2.300 (6, 6); 0.008 (0.5); 0.000 (16.2)
Beispiel No. A2-1 : 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. A2-1: 1 H-NMR (400 MHz, CDCIs δ, ppm)
7,746(1 ,1 );7,742(1 ,2);7,728(1 ,3);7,723(1 ,3);7,520(1 ,0);7,471 (1 ,2);7,467(1 ,4);7,451 (1 ,8) ;7,447(2,0);7,400(0,8);7,395(0,9);7,381 (1 ,5);7,377(1 ,4);7,362(1 ,0);7,357(0,9);7,339(1 ,2 );7,335(1 ,2);7,320(1 ,6);7,317(1 ,6);7,301 (0,7);7,298(0,6);7,2734(0,6);7,2726(0,6);7,272( 0,7);7,271 (0,7);7,270(0,8);7,2694(1 ,0);7,2687(1 ,1 );7,268(1 ,2);7,267(1 ,5);7,266(1 ,9);7,2 654(2,4);7,2646(3,1 );7,261 (178,4);7,2573(4,4);7,2565(2,8);7,256(1 ,6);7,255(1 ,2);7,254 (0,9);7,253(0,8);7,2524(0,6);7,2516(0,5);7,251 (0,5);6,997(0,9);5,300(2,0);5,197(5,2);3, 766(8,2);3,765(8,3);3,394(16,0);1 ,552(8,5);0,008(1 ,8);0,006(0,6);0,0054(0,7);0,0046(0, 9);0,004(1 ,1 );0,002(2,9);0,000(60,8);-0,003(3,1 );-0,004(1 ,1 );-0,005(0,7);-0,006(0,6);- 0,007(0,5);-0,009(1 ,8) Beispiel No. A2-21 : 1H-NMR (400 MHz, CDCIs δ, ppm) 7,746 (1, 1); 7,742 (1,2), 7,728 (1,3), 7,723 (1,3), 7,520 (1, 0), 7,471 (1,2), 7,467 (1,4), 7,451 (1, 8); 7.477 (2.0); 7,400 (0.8); 7,395 (0.9); 7,381 (1, 5); 7,377 (1, 4); 7,362 (1, 0); 7,357 ( 7.399 (1, 2), 7.339 (1, 2), 7.339 (1, 6), 7.317 (1, 6), 7.301 (0.7), 7.298 (0.6), 7.2734 (0.6), 7.2726 (0.6), 7.272 (0.7), 7.271 (0.7), 7.270 (0.8), 7.2694 (1.0), 7.2687 (1 7,266 (1, 5); 7,266 (1, 9); 7,2654 (2,4); 7,2646 (3,1); 7,261 (178,4); 7,255 (1,4); 7,255 (1,2); (0.6); 7.2516 (0.5); 7.251 (0.5); 6.997 (0.9); 5.300 (2.0); 5.197 (5.2); 3, 766 (8.2 3,765 (8.3); 3.394 (16.0); 1, 552 (8.5); 0.008 (1, 8); 0.006 (0.6); 0.0054 (0.7); 0, 0046 (0, 9), 0.004 (1, 1), 0.002 (2.9), 0.000 (60.8), - 0.003 (3.1), - 0.004 (1, 1), - 0.005 (0.7 - 0.006 (0.6) - 0.007 (0.5) - 0.009 (1, 8) Example no. A2-21: 1 H-NMR (400 MHz, CDCl3 δ, ppm)
8,629(2,3);8,617(2,3);7,752(0,8);7,729(2,0);7,714(1 ,8);7,689(2,2);7,671 (1 ,1 );7,520(3,4) ;7,349(1 ,4);7,336(1 ,8);7,318(1 ,2);7,287(0,6);7,285(0,6);7,278(1 ,2);7,2773(1 ,2);7,2765( 1 ,2);7,276(1 ,4);7,275(1 ,4);7,274(1 ,6);7,2734(1 ,6);7,2725(1 ,9);7,272(2,2);7,271 (2,6);7,2 70(3,0);7,2693(3,6);7,2685(4,0);7,268(4,7);7,267(5,5);7,266(6,7);7,265(8,3);7,261 (630, 4);7,2564(9,7);7,2556(6,2);7,255(3,9);7,254(2,9);7,253(2,3);7,2523(1 ,9);7,2515(1 ,6);7, 251 (1 ,5);7,250(1 ,5);7,249(1 ,4);7,2483(1 ,4);7,2475(1 ,1 );7,247(1 ,0);7,246(0,9);7,245(0,8 );7,2444(0,7);7,2435(0,6);7,243(0,6);7,242(0,6);7,241 (0,6);7,2404(0,6);7,2395(0,6);7,2 39(0,7);7,238(0,6);7,2332(0,7);7,2325(0,6);7,21 1 (0,8);6,997(3,3);5,300(2,1 );5,089(5,1 ); 3,739(16,0);3,649(0,7);3,450(13,3);2,092(3,4);1 ,552(6,4);1 ,329(0,6);1 ,255(1 ,9);0,880(0 ,6);0,146(0,6);0,008(6,1 );0,000(220,5);-0,009(5,9);-0,150(0,6) 8.629 (2.3); 8.617 (2.3); 7.752 (0.8); 7.729 (2.0); 7.714 (1, 8); 7.689 (2.2); 7.671 (1, 1); 7.520 (3,4); 7,349 (1,4), 7,336 (1, 8), 7,318 (1,2), 7,287 (0,6), 7,285 (0,6), 7,278 (1,2), 773 (1, 2); 7,276 (1, 2); 7,276 (1,4); 7,275 (1,4); 7,274 (1,6); 7,2734 (1,6); 1, 9), 7.272 (2.2), 7.271 (2.6), 7.2 70 (3.0); 7.2693 (3.6) 7.2685 (4.0); 7,268 (4.7); 7,267 (5.5); 7,266 (6.7); 7,265 (8, 3); 7.261 (630, 4); 7.2564 (9.7); 7.2556 (6.2); 7.255 (3.9); 7.254 (2.9); 7.253 (2.3); 7 , 2523 (1, 9); 7,2515 (1, 6); 7, 251 (1, 5); 7,250 (1, 5); 7,249 (1, 4); 7,2483 (1, 4); 7 , 2475 (1, 1), 7.247 (1, 0), 7.246 (0.9), 7.245 (0.8), 7.2444 (0.7), 7.2435 (0.6), 7.243 (0 7,242 (0.6); 7.241 (0.6); 7.2404 (0.6); 7.2395 (0.6); 7.2 39 (0.7); 7.238 (0); 7,2332 (0.7), 7.2325 (0.6), 7.21 1 (0.8), 6.997 (3.3), 5.300 (2.1), 5.089 (5.1 ); 3,739 (16.0); 3.649 (0.7); 3,450 (13.3); 2.092 (3.4); 1, 552 (6.4); 1, 329 (0.6); 1, 255 ( 1, 9), 0.880 (0, 6), 0.146 (0.6), 0.008 (6.1), 0.000 (220.5), - 0.009 (5.9), - 0.150 (0.6)
Beispiel No. A2-37: 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. A2-37: 1 H-NMR (400 MHz, CDCIs δ, ppm)
8,281 (1 ,8);7,268(0,5);7,267(0,8);7,262(62,4);5,098(1 ,5);3,787(16,0);3,758(4,2);3,757(4 ,3);3,459(4,4);2,452(8,2);2,296(6,5);0,008(0,6);0,000(20,3);-0,009(0,5) 7.281 (1, 8), 7.268 (0.5), 7.267 (0.8), 7.262 (62.4), 5.098 (1.5), 3.787 (16.0), 3.758 (4.2), 3.757 (4, 3); 3.459 (4.4); 2.452 (8.2); 2.296 (6.5); 0.008 (0.6); 0.000 (20.3); 0.009 (0.5)
Beispiel No. A2-44: 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. A2-44: 1 H-NMR (400 MHz, CDCIs δ, ppm)
7,550(0,9);7,529(1 ,8);7,519(1 ,5);7,510(1 ,3);7,367(1 ,3);7,361 (1 ,9);7,349(1 ,6);7,344(3,0) ;7,325(1 ,9);7,320(1 ,4);7,260(257,6);7,255(0,8);7,254(0,6);6,996(1 ,4);5,300(6,8);5,019( 4,9);3,759(8,8);3,757(8,8);3,364(16,0);3,362(16,0);1 , 545(21 , 7);0,010(0,6);0,009(0,7);0, 008(3,1 );0,0063(1 ,2);0,0055(1 ,3);0,005(1 ,6);0,004(2,0);0,003(3,0);0,002(4,8);0,000(89, 4);-0,003(4,0);-0,0035(2,6);-0,0044(1 ,4);-0,005(0,8);-0,006(0,6);-0,007(0,6);-0,009(2,4). Beispiel No. A4-21 : 1H-NMR (400 MHz, CDCIs δ, ppm) 7.550 (0.9), 7.529 (1, 8), 7.519 (1, 5), 7.510 (1.3), 7.367 (1.3), 7.361 (1.9), 7.349 (1, 6), 7.344 (3.0); 7.325 (1, 9); 7.320 (1, 4); 7.260 (257.6); 7.255 (0.8); 7.254 (0.6); 6.996 (1, 4); 6.8), 5.019 (4.9), 3.759 (8.8), 3.757 (8.8), 3.364 (16.0), 3.362 (16.0), 1.555 (21, 7), 0.010 (0.6); 0.009 (0.7); 0.008 (3.1); 0.0063 (1, 2); 0.0055 (1.3); 0.005 (1.6); 0.004 (2 , 0), 0.003 (3.0), 0.002 (4.8), 0.000 (89, 4), - 0.003 (4.0), - 0.0035 (2.6), - 0.0044 (1, 4) - 0.005 (0.8) - 0.006 (0.6) - 0.007 (0.6) - 0.009 (2.4). Example No. A4-21: 1 H-NMR (400 MHz, CDCl3 δ, ppm)
8,629(1 ,5);8,626(1 ,7);8,624(1 ,8);8,622(1 ,6);8,617(1 ,6);8,614(1 ,7);8,612(1 ,7);8,610(1 ,5) ;7,732(0,8);7,728(0,9);7,713(2,1 );7,708(2,1 );7,694(1 ,6);7,689(1 ,6);7,652(2,4);7,649(3,7 );7,647(2,7);7,633(1 ,6);7,630(2,1 );7,627(1 ,4);7,521 (0,6);7,343(1 ,3);7,340(1 ,4);7,331 (1 , 4);7,328(1 ,4);7,324(1 ,4);7,321 (1 ,2);7,312(1 ,3);7,309(1 ,2);7,263(1 13,4);6,999(0,6);5,30 0(4,9);5,127(7,4);3,873(16,0);3,447(1 1 ,9);1 ,619(0,7);1 ,259(0,9);1 ,255(0,9);0,008(1 ,0);0 ,000(32,9);-0,009(1 ,0)  8.629 (1, 5), 8.626 (1, 7), 8.624 (1, 8), 8.622 (1, 6), 8.617 (1, 6), 8.614 (1, 7), 8.612 (1, 7), 8.610 (1, 5); 7,732 (0.8); 7,728 (0.9); 7,713 (2,1); 7,708 (2,1); 7,694 (1, 6); 7,689 (1, 6); 7,652 ( 2.4), 7.649 (3.7), 7.647 (2.7), 7.633 (1.6), 7.630 (2.1), 7.627 (1.4), 7.521 (0.6), 7.343 (1 7,324 (1, 4); 7,324 (1, 4); 7,324 (1, 4); 7,321 (1, 2); 7,312 (1, 3); 7,309 (1, 4); 2); 7.263 (1 13.4); 6.999 (0.6); 5.30 0 (4.9); 5.127 (7.4); 3.873 (16.0); 3.347 (1 1, 9); 1, 619 (0.7); 1, 259 (0.9); 1, 255 (0.9); 0.008 (1, 0); 0, 000 (32.9); - 0.009 (1, 0)
Beispiel No. A4-37: 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. A4-37: 1 H-NMR (400 MHz, CDCIs δ, ppm)
8,282(2,0);7,264(31 ,9);5,300(5,2);5,132(3,1 );3,895(6,9);3,781 (16,0);3,453(5,9);2,446(8 ,5);2,295(7,5);0,000(9,9)  8.282 (2.0), 7.264 (31, 9), 5.300 (5.2), 5.122 (3.1), 3.895 (6.9), 3.781 (16.0), 3.453 (5.9), 2.446 (8, 5); 2,295 (7,5); 0,000 (9,9)
Beispiel No. A4-44: 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. A4-44: 1 H-NMR (400 MHz, CDCIs δ, ppm)
7,663(1 ,0);7,521 (1 ,1 );7,494(1 ,4);7,474(2,8);7,454(1 ,5);7,340(4,8);7,319(4,3);7,262(192 ,5);7,212(0,5);6,998(1 ,1 );5,300(16,0);5,070(4,9);4,131 (0,7);4,1 13(0,7);3,884(1 1 ,0);3,35 1 (13,5);2,045(4,1 );1 ,594(1 ,9);1 ,277(1 ,1 );1 ,259(2,6);1 ,241 (1 ,1 );0,936(0,7);0,008(1 ,6);0, 000(57,1 );-0,009(1 , 7) Beispiel No. A5-1 : 1H-NMR (400 MHz, CDCIs δ, ppm) 7.663 (1, 0); 7.521 (1, 1); 7.494 (1, 4); 7.474 (2.8); 7.454 (1, 5); 7.340 (4.8); 7.319 (4.3); 7.262 (192 , 5), 7.212 (0.5), 6.998 (1, 1), 5.300 (16.0), 5.070 (4.9), 4.131 (0.7), 4.1 13 (0.7), 3.884 (1 1, 0); 3.35 1 (13.5); 2.045 (4.1); 1, 594 (1, 9); 1, 277 (1, 1); 1, 259 (2.6) ; 1, 241 (1, 1); 0.936 (0.7); 0.008 (1, 6); 0, 000 (57.1); - 0.009 (1, 7) A5-1: 1 H-NMR (400 MHz, CDCIs δ, ppm)
7,681 (1 ,1 );7,666(1 ,3);7,662(1 ,3);7,520(0,9);7,484(0,6);7,479(1 ,6);7,476(1 ,9);7,469(0,6) ;7,459(2,7);7,456(2,5);7,405(1 ,2);7,401 (1 ,3);7,392(0,8);7,387(1 ,8);7,382(1 ,8);7,367(1 ,1 );7,362(1 ,0);7,332(1 ,3);7,328(1 ,4);7,313(2,0);7,309(2,3);7,294(0,9);7,290(2,4);7,284(0, 6);7,281 (1 ,4);7,278(0,5);7,275(1 ,4);7,274(0,8);7,273(0,7);7,272(0,7);7,271 (0,8);7,270(0 ,9);7,269(1 ,0);7,267(3,1 );7,265(2,8);7,261 (170,7);7,171 (2,1 );7,035(1 ,1 );6,997(0,9);5,30 0(1 ,7);5,180(4,9);4,710(4,9);3,879(0,8);3,777(9,4);3,776(10,2);3,401 (16,0);1 ,565(8,1 );1 ,432(1 ,0);1 ,256(3,0);1 ,222(1 ,0);0,880(0,9);0,875(0,6);0,853(0,7);0,069(3,4);0,008(1 ,6); 0,000(58,9);-0,009(1 ,6) Beispiel No. A5-1 1 : 1H-NMR (400 MHz, CDCIs δ, ppm) 7.681 (1, 1), 7.666 (1, 3), 7.662 (1, 3), 7.520 (0.9), 7.484 (0.6), 7.479 (1, 6), 7.466 (1, 9), 7.469 (0.6); 7.459 (2.7); 7.456 (2.5); 7.405 (1, 2); 7.401 (1, 3); 7.392 (0.8); 7.387 (1, 8); 1, 8), 7.367 (1, 1), 7.362 (1, 0), 7.332 (1, 3), 7.328 (1, 4), 7.313 (2.0), 7.309 (2.3), 7.294 (0 7,278 (1, 4); 7,278 (0.5); 7,275 (1, 4); 7,274 (0.8); 7,273 (0, 6); 7,284 (0, 6); 7), 7.272 (0.7), 7.271 (0.8), 7.270 (0.9), 7.269 (1.0), 7.267 (3.1), 7.265 (2.8), 7.261 (170.7 7,171 (2,1), 7,035 (1,1), 6,997 (0,9), 5,30 0 (1, 7), 5,180 (4,9), 4,710 (4,9), 3,879 (0 , 8); 3,777 (9.4); 3,776 (10,2); 3,401 (16,0); 1, 565 (8,1); 1, 432 (1, 0); 1, 256 (3,0 1, 222 (1, 0), 0.880 (0.9), 0.875 (0.6), 0.853 (0.7), 0.069 (3.4), 0.008 (1, 6); 0.000 (58.9); - 0.009 (1, 6) Example no. A5-1 1: 1 NMR (400 MHz, CDCIs δ, ppm)
7,587(0,6);7,583(0,7);7,568(1 ,2);7,564(1 ,3);7,550(0,8);7,545(0,7);7,521 (0,6);7,473(0,6) ;7,463(0,6);7,459(1 ,1 );7,454(0,9);7,445(0,8);7,443(0,8);7,438(1 ,2);7,433(0,8);7,424(0,7 );7,420(0,7);7,292(1 ,4);7,262(1 1 1 ,7);7,221 (1 ,2);7,218(1 ,4);7,202(2,0);7,199(2,3);7,183( 1 ,0);7,180(1 ,2);7,175(1 ,5);7,172(1 ,3);7,156(3,3);7,150(1 ,9);7,147(1 ,3);7,129(1 ,1 );7,126 (1 ,0);7,020(1 ,4);6,998(0,6);5,300(3,4);5,1 19(0,5);5,037(4,6);4,386(1 ,3);4,368(1 ,3);4,07 4(0,7);3,872(0,9);3,770(9,3);3,768(10,0);3,687(2,6);3,377(16,0);1 , 581 (3,7);1 , 348(1 ,3);1 ,330(2,5);1 ,312(1 ,4);1 ,256(6,4);1 ,242(1 ,4);1 ,227(0,9);1 ,222(2,6);1 ,164(0,6);0,897(0,7); 0,880(1 ,7);0,874(1 ,3);0,870(1 ,1 );0,863(1 ,1 );0,857(1 ,2);0,853(1 ,4);0,836(1 ,0);0,069(1 ,6) ;0,008(1 ,1 );0,000(39,8);-0,009(1 ,2)  7,587 (0,6), 7,583 (0,7), 7,568 (1,2), 7,564 (1,3), 7,550 (0,8), 7,545 (0,7), 7,521 (0,6), 7,473 (0.6); 7.463 (0.6); 7.459 (1, 1); 7.454 (0.9); 7.445 (0.8); 7.443 (0.8); 7.438 (1, 2); 7.433 (7) 7.424 (0.7), 7.420 (0.7), 7.292 (1, 4), 7.262 (1 1, 1, 7), 7.221 (1.2), 7.218 (1, 4), 7.202 (2.0); 7.199 (2.3); 7.183 (1, 0); 7.180 (1, 2); 7.175 (1.5); 7.172 (1.3); 7.156 (3.3); 7.150 ( 1, 9), 7.147 (1, 3), 7.129 (1, 1), 7.126 (1, 0), 7.020 (1, 4), 6.998 (0.6), 5.300 (3.4), 5.1 19 (0.5), 5.037 (4.6), 4.386 (1.3), 4.368 (1.3), 4.07 4 (0.7), 3.872 (0.9), 3.770 (9.3 3,768 (10,0); 3,687 (2,6); 3,377 (16,0); 1, 581 (3,7); 1, 348 (1, 3); 1, 330 (2.5); 1, 312 (1, 4); 1, 256 (6.4); 1, 242 (1, 4); 1, 227 (0.9); 1, 222 (2.6); 1, 164 (0 , 6); 0.897 (0.7); 0.880 (1, 7), 0.874 (1.3), 0.870 (1, 1), 0.863 (1, 1), 0.857 (1.2), 0.853 (1.4), 0.836 (1.0), 0.069 (1, 6), 0.008 (1, 1), 0.000 (39.8), - 0.009 (1, 2)
Beispiel No. A5-13: 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. A5-13: 1 H-NMR (400 MHz, CDCls δ, ppm)
7,607(0,6);7,602(1 ,1 );7,586(1 ,1 );7,581 (0,6);7,565(0,5);7,341 (0,5);7,325(0,5);7,278(1 ,5) ;7,264(25,2);7,142(2,9);7,006(1 ,5);6,954(0,5);6,952(0,6);6,939(0,8);6,932(1 ,1 );6,923(0, 9);6,917(0,8);6,913(0,6);6,91 1 (0,7);6,902(1 ,0);6,898(1 ,0);6,892(0,7);6,877(0,8);6,870(0 ,6);6,809(0,5);4,994(4,4);4,400(2,2);4,398(2,2);3,765(7,2);3,764(7,7);3,371 (15,4);3,369 (16,0);2,955(0,7);2,884(0,6);2,882(0,6);1 ,258(1 ,0);1 ,256(1 ,0);0,000(10,0) Beispiel No. A5-21 : 1H-NMR (400 MHz, CDCIs δ, ppm) 7.607 (0.6), 7.602 (1, 1), 7.586 (1, 1), 7.581 (0.6), 7.565 (0.5), 7.341 (0.5), 7.325 (0.5), 7.278 (1, 5), 7.264 (25.2), 7.142 (2.9), 7.006 (1.5), 6.954 (0.5), 6.952 (0.6), 6.939 (0.8), 6.932 ( 1, 1); 6.923 (0.9); 6.917 (0.8); 6.913 (0.6); 6.91 1 (0.7); 6.902 (1.0); 6.898 (1.0); 6.892 (0.7), 6.877 (0.8), 6.870 (0, 6), 6.809 (0.5), 4.994 (4.4), 4.400 (2.2), 4.398 (2.2), 3.765 (7,2); 3,764 (7,7); 3,371 (15,4); 3,369 (16,0); 2,955 (0,7); 2,884 (0,6); 2,882 (0,6); 1, 258 (1, 0); 1, 256 (1, 0); 0.000 (10.0) Example No. A5-21: 1 H-NMR (400 MHz, CDCIs δ, ppm)
8,640(1 ,2);8,638(1 ,3);8,636(1 ,4);8,633(1 ,2);8,628(1 ,2);8,626(1 ,3);8,623(1 ,3);8,621 (1 ,1 ) ;7,747(0,8);7,742(0,8);7,727(1 ,8);7,723(1 ,8);7,708(1 ,2);7,704(1 ,3);7,633(1 ,6);7,614(1 ,1 );7,359(1 ,2);7,356(1 ,2);7,347(1 ,2);7,344(1 ,2);7,340(1 ,2);7,337(1 ,1 );7,328(1 ,1 );7,325(1 , 0);7,263(76,2);7,210(1 ,4);7,073(3,1 );6,937(1 ,5);5,058(5,5);3,755(7,9);3,754(8,4);3,752( 7,8);3,460(16,0);1 ,603(0,9);1 ,254(0,6);0,008(0,7);0,000(20,6);-0,009(0,6)  8.640 (1, 2), 8.638 (1, 3), 8.636 (1, 4), 8.633 (1, 2), 8.628 (1, 2), 8.626 (1, 3), 8.623 (1, 3), 8.621 (1, 1); 7.747 (0.8); 7.742 (0.8); 7.727 (1, 8); 7.723 (1, 8); 7.708 (1, 2); 7.704 (1, 3); 7.633 ( 1, 6), 7.614 (1, 1), 7.359 (1,2), 7,356 (1,2), 7,347 (1,2), 7,344 (1,2), 7,340 (1,2), 7,337 (1 7,328 (1, 1); 7,325 (1, 0); 7,263 (76,2); 7,210 (1, 4); 7,073 (3,1); 6,937 (1, 5); 5,058 (5, 5); 5), 3.755 (7.9), 3.754 (8.4), 3.752 (7.8), 3.460 (16.0), 1.603 (0.9), 1.254 (0.6), 0.008 (0.7); 0,000 (20.6) - 0.009 (0.6)
Beispiel No. A5-30: 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. A5-30: 1 H-NMR (400 MHz, CDCIs δ, ppm)
7,264(14,6);7,222(0,6);6,054(2,1 );5,300(0,7);4,978(1 ,7);3,943(16,0);3,760(1 ,9);3,759(2 ,0);3,757(2,0);3,609(5,0);0,000(4,2)  7.264 (14.6); 7.222 (0.6); 6.054 (2.1); 5,300 (0.7); 4,978 (1, 7); 3,943 (16,0); 3,760 (1,9); 3,759 (2, 0); 3.757 (2.0); 3.609 (5.0); 0.000 (4.2)
Beispiel No. A5-37: 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. A5-37: 1 H-NMR (400 MHz, CDCIs δ, ppm)
8,282(3,3);7,519(2,0);7,309(1 ,3);7,261 (356,9);7,21 1 (3,4);6,997(2,0);5,083(1 ,0);3,788(1 6,0);3,765(6,8);3,473(2,9);2,685(0,7);2,449(1 1 ,2);2,350(0,7);2,299(1 1 ,7);2,266(0,7);1 ,5 53(5,7);1 ,432(1 ,7);1 ,257(1 ,2);1 ,222(0,6);0,008(3,4);0,000(106,9);-0,009(3,2);- 0,050(0,9)  8,282 (3.3), 7.519 (2.0), 7.309 (1.3), 7.261 (356.9), 7.21 1 (3.4), 6.997 (2.0), 5.083 (1.0 3.788 (1 6.0), 3.765 (6.8), 3.473 (2.9), 2.685 (0.7), 2.449 (1 1, 2), 2.350 (0.7), 2.299 (1 1 , 7); 2,266 (0,7); 1, 5 53 (5,7); 1, 432 (1, 7); 1, 257 (1, 2); 1, 222 (0.6); 0.008 ( 3.4), 0.000 (106.9), - 0.009 (3.2), - 0.050 (0.9)
Beispiel No. A5-44: 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. A5-44: 1 H-NMR (400 MHz, CDCIs δ, ppm)
7,521 (0,7);7,496(0,6);7,476(1 ,5);7,456(1 ,1 );7,362(1 ,7);7,358(6,8);7,337(2,3);7,335(3,8) ;7,330(1 ,8);7,310(0,5);7,308(0,9);7,307(1 ,1 );7,305(1 ,0);7,303(0,7);7,299(0,8);7,296(0,8 );7,289(0,6);7,288(0,5);7,286(0,7);7,282(0,5);7,277(1 ,7);7,2734(0,8);7,2726(0,8);7,272( 0,7);7,271 (0,9);7,270(1 ,0);7,2694(1 ,0);7,2685(1 ,1 );7,268(1 ,4);7,262(127,8);7,141 (2,9); 7,004(1 ,4);6,998(0,8);5,300(7,5);4,995(4,7);4,584(2,1 );4,581 (2,0);4,363(0,8);4,345(0,7) ;4,060(0,6);3,869(1 ,0);3,766(1 1 ,3);3,687(1 ,6);3,374(16,0);1 ,580(4,1 );1 ,432(0,9);1 ,348( 0,7);1 ,330(1 ,4);1 ,313(0,8);1 ,256(3,0);1 ,222(1 ,7);0,880(0,9);0,874(0,6);0,853(0,7);0,069 (2,0);0,008(1 ,2);0,000(43,8);-0,009(1 ,2)  7.456 (0.7); 7.496 (0.6); 7.466 (1, 5); 7.456 (1, 1); 7.362 (1, 7); 7.358 (6.8); 7.377 (2.3); 7.335 (3,8); 7,330 (1, 8); 7,310 (0.5); 7,308 (0.9); 7,307 (1, 1); 7,305 (1, 0); 7,303 (0,7); 7,299 ( 7,296 (0.8), 7.289 (0.6), 7.288 (0.5), 7.286 (0.7), 7.282 (0.5), 7.277 (1, 7), 7.2734) (0.8); 7.2726 (0.8); 7.272 (0.7); 7.271 (0.9); 7.270 (1.0); 7.2694 (1.0); 7.2685 (1 , 1), 7.268 (1, 4), 7.262 (127.8), 7.141 (2.9); 7.004 (1, 4), 6.998 (0.8), 5.300 (7.5), 4.995 (4.7), 4.584 (2.1), 4.581 (2.0), 4.363 (0.8), 4.345 (0.7); 4.060 (0.6); 3.869 (1, 0); 3.766 (1, 1, 3); 3.687 (1, 6); 3.374 (16.0); 1, 580 (4.1) 1, 432 (0.9); 1, 348 (0.7); 1, 330 (1, 4); 1, 313 (0.8); 1, 256 (3.0); 1, 222 ( 1, 7), 0.880 (0.9), 0.874 (0.6), 0.853 (0.7), 0.069 (2.0), 0.008 (1, 2), 0.000 (43.8), - 0.009 ( 1, 2)
Beispiel No. A6-1 : 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. A6-1: 1 H-NMR (400 MHz, CDCIs δ, ppm)
7,666(1 ,0);7,662(1 ,0);7,647(1 ,2);7,643(1 ,1 );7,482(0,9);7,479(1 ,0);7,462(1 ,4);7,459(1 ,5) ;7,405(0,7);7,401 (0,8);7,387(1 ,2);7,382(1 ,1 );7,367(0,8);7,362(0,7);7,329(0,9);7,325(0,9 );7,310(1 ,3);7,307(1 ,2);7,291 (1 ,8);7,288(0,6);7,263(28,3);7,155(2,7);7,018(1 ,4);5,300(5 ,0);5,241 (5,1 );3,879(10,0);3,400(16,0);2,045(0,6);0,000(10,2) Beispiel No. A6-44: 1H-NMR (400 MHz, CDCIs δ, ppm) 7.666 (1, 0); 7.662 (1, 0); 7.647 (1, 2); 7.643 (1, 1); 7.482 (0.9); 7.499 (1, 0); 7.462 (1, 4); (1, 5); 7.405 (0.7); 7.401 (0.8); 7.387 (1, 2); 7.382 (1, 1); 7.367 (0.8); 7.362 (0.7); 7.329 ( 7.357 (1, 2), 7.291 (1, 8), 7.288 (0.6), 7.263 (28.3), 7.155 (2, 0.9); , 7); 7.018 (1, 4); 5,300 (5, 0); 5,241 (5,1); 3,879 (10,0); 3,400 (16,0); 2,045 (0,6); 0,000 (10, 2) Example No. A6-44: 1 H-NMR (400 MHz, CDCIs δ, ppm)
7,489(1 ,0);7,469(1 ,9);7,449(1 ,0);7,362(1 ,2);7,358(3,2);7,336(4,9);7,263(73,2);7,257(2, 1 );7,120(3,9);6,984(1 ,9);5,300(10,3);5,067(4,8);3,870(16,0);3,372(14,4);2,069(0,9);2,0 45(2,2);1 ,277(0,7);1 ,259(1 ,4);1 ,241 (0,6);0,008(0,8);0,002(1 ,1 );0,000(24,7);-0,009(0,7)  7.499 (1, 0), 7.469 (1, 9), 7.499 (1, 0), 7.362 (1, 2), 7.358 (3.2), 7.366 (4.9), 7.263 (73.2), 7.257 (2, 1); 7.120 (3.9); 6.984 (1, 9); 5,300 (10,3); 5,067 (4.8); 3,870 (16,0); 3,372 (14.4); 2,069 ( 0.9); 2.0 45 (2.2); 1, 277 (0.7); 1, 259 (1, 4); 1, 241 (0.6); 0.008 (0.8); 0.002 (1, 1); 0.000 (24.7); - 0.009 (0.7)
Beispiel No. A7-1 : 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. A7-1: 1 H-NMR (400 MHz, CDCIs δ, ppm)
7,694(0,7);7,690(0,8);7,675(0,9);7,670(0,9);7,479(0,7);7,475(0,8);7,459(1 ,1 );7,455(1 ,2) ;7,405(0,6);7,401 (0,6);7,387(1 ,0);7,382(1 ,0);7,367(0,7);7,362(0,6);7,338(0,8);7,334(0,8 );7,319(1 ,0);7,315(1 ,0);7,300(0,5);7,296(1 ,2);7,264(21 ,6);7,160(2,0);7,024(1 ,0);5,300(2 ,5);5,185(4,4);4,123(1 ,3);4,105(1 ,3);3,402(16,0);1 ,619(0,8);1 ,468(2,7);1 ,450(6,0);1 ,432 (2,7);0,000(7,4)  7.694 (0.7), 7.690 (0.8), 7.675 (0.9), 7.670 (0.9), 7.499 (0.7), 7.475 (0.8), 7.459 (1, 1), 7.455 (1,2), 7.405 (0.6), 7.401 (0.6), 7.387 (1, 0), 7.382 (1, 0), 7.367 (0.7), 7.362 (0.6), 7.338 ( 7,334 (1, 0); 7,300 (0.5); 7,296 (1,2); 7,264 (21,6); 7,160 (2,8); , 0, 7,024 (1,0), 5,300 (2,5), 5,185 (4,4), 4,123 (1,3), 4,105 (1,3), 3,402 (16,0), 1, 619 ( 0.8); 1, 468 (2.7); 1, 450 (6.0); 1, 432 (2.7); 0.000 (7.4)
Beispiel No. A7-21 : 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. A7-21: 1 H-NMR (400 MHz, CDCIs δ, ppm)
8,641 (1 ,0);8,639(1 ,0);8,636(1 ,1 );8,634(1 ,0);8,629(1 ,0);8,626(1 ,1 );8,624(1 ,0);8,622(0,9) ;7,752(0,6);7,748(0,6);7,733(1 ,5);7,728(1 ,5);7,714(1 ,0);7,709(1 ,0);7,640(1 ,4);7,620(1 ,0 );7,360(1 ,0);7,357(1 ,0);7,348(1 ,0);7,344(0,9);7,341 (0,9);7,338(0,8);7,329(0,8);7,326(0, 8);7,271 (0,5);7,270(0,6);7,269(0,7);7,268(0,9);7,262(69,7);7,195(1 ,2);7,058(2,7);6,922( 8.641 (1, 0); 8.639 (1, 0); 8.636 (1, 1); 8.634 (1, 0); 8.629 (1, 0); 8.626 (1, 1); 8.624 (1.0); 8.622 7.748 (1, 5); 7.714 (1, 5); 7.714 (1, 0); 7.702 (0.6); 7.748 (0.6); 7.733 (1, 5); 7.702 (1, 5); 1, 4); 7,620 (1, 0); 7,360 (1, 0); 7,357 (1, 0); 7,348 (1, 0); 7,344 (0,9); 7,341 (0,9); 7,338 (0 , 7,329 (0,8); 7,326 (0, 8); 7,271 (0.5); 7,270 (0,6); 7,269 (0,7); 7,268 (0,9); 7,262 (69); 7), 7.195 (1, 2), 7,058 (2,7), 6,922 (
1 .3) ;5,061 (5,1 );4,120(0,6);4,102(1 ,9);4,084(1 ,9);4,065(0,6);3,470(2,7);3,459(16,0);1 ,59 5(1 ,2);1 ,451 (4,0);1 ,432(8,8);1 ,414(4,0);0,008(0,8);0,000(25,0);-0,009(0,7) 5.01 (5.1), 4.120 (0.6), 4.102 (1.9), 4.084 (1.9), 4.065 (0.6), 3.470 (2.7), 3.459 (16 , 0); 1, 59 5 (1, 2); 1, 451 (4.0); 1, 432 (8.8); 1, 414 (4.0); 0.008 (0.8); 0.000 ( 25.0) - 0.009 (0.7)
Beispiel No. A8-35: 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. A8-35: 1 H-NMR (400 MHz, CDCls δ, ppm)
8,588(1 ,4);8,583(1 ,4);8,029(1 ,5);8,023(1 ,4);7,619(0,7);7,615(1 ,2);7,612(0,6);7,551 (0,8) ;7,414(1 ,6);7,277(0,8);5,096(4,7);3,832(5,7);3,448(16,0);2,134(12,0);1 ,964(2,3);1 ,958( 8,588 (1,4), 8,583 (1,4), 8,029 (1,5), 8,023 (1,4), 7,619 (0,7), 7,615 (1,2), 7,612 (0,6), 7,551 (0.8); 7.414 (1, 6); 7.277 (0.8); 5.096 (4.7); 3.832 (5.7); 3.448 (16.0); 2.134 (12.0); 1, 964 (2,3); 1, 958 (
3.4) ;1 ,952(15,1 );1 ,946(26,3);1 ,940(34,4);1 ,933(23,7);1 ,927(12,2);1 ,921 (0,4);0,000(0,8) 1, 934 (26, 4); 1, 940 (34.4); 1, 933 (23, 7); 1, 927 (12, 2); 921 (0.4); 0.000 (0.8)
Beispiel No. A8-36: 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. A8-36: 1 H-NMR (400 MHz, CDCIs δ, ppm)
8,887(1 ,0);8,884(1 ,0);8,257(1 ,0);8,253(0,9);7,61 1 (0,9);7,608(1 ,4);7,510(0,8);7,373(1 ,7) ;7,237(0,8);5,179(4,4);4,086(0,5);4,068(1 ,4);4,050(1 ,5);4,032(0,5);3,828(6,2);3,510(16, 0);2,144(4,0);1 ,972(6,4);1 ,964(0,8);1 ,958(1 ,2);1 ,952(5,1 );1 ,946(8,9);1 ,940(1 1 ,6);1 ,934( 8,0);1 ,927(4,1 );1 ,222(1 ,8);1 ,204(3,5);1 ,186(1 ,8)  8.887 (1, 0), 8.884 (1, 0), 8.257 (1, 0), 8.253 (0.9), 7.61 1 (0.9), 7.608 (1, 4), 7.510 (0.8 7.373 (1, 7); 7.237 (0.8); 5.179 (4.4); 4.086 (0.5); 4.068 (1, 4); 4.050 (1, 5); 4.032 (0.5) 3,828 (6,2); 3,510 (16, 0); 2,144 (4,0); 1,972 (6,4); 1,964 (0,8); 1,958 (1, 2); 1 , 952 (5.1); 1, 946 (8.9); 1, 940 (1 1, 6); 1, 934 (8.0); 1, 927 (4.1); 1, 222 (1 , 8); 1, 204 (3,5); 1, 186 (1, 8)
Beispiel No. A12-1 : 1H-NMR (600 MHz, de-DMSO δ, ppm) Example No. A12-1: 1 H-NMR (600 MHz, de-DMSO δ, ppm)
7,826(1 ,6);7,547(0,7);7,490(2,4);7,486(2,6);7,474(3,3);7,391 (0,9);7,380(2,3);7,376(2,8) ;7,372(4,0);7,367(2,1 );7,364(2,7);7,361 (2,5);7,352(0,8);7,265(0,5);4,928(0,5);4,819(0,6 );4,002(0,4);3,932(16,0);3,917(0,8);3,908(0,4);3,378(18,5);3,373(24,4);3,369(23,9);3,3 64(40,1 );3,361 (34,2);3,358(48,4);3,355(65,3);3,054(1 ,9);2,624(0,4);2,530(0,7);2,527(0, 7);2,515(47,8);2,512(66,8);2,509(49,4);2,396(0,4);1 ,495(0,4);1 ,362(0,8);1 ,267(0,4);1 ,2 36(0,4);0,993(5,6);0,008(0,3) 7.826 (1, 6); 7.547 (0.7); 7.490 (2.4); 7.486 (2.6); 7.474 (3.3); 7.391 (0.9); 7.380 (2.3); 7.376 (2.8) 7.372 (4.0), 7.367 (2.1), 7.364 (2.7), 7.361 (2.5), 7.352 (0.8), 7.265 (0.5), 4.928 (0.5); 4,819 (0.6), 4.002 (0.4), 3.932 (16.0), 3.917 (0.8), 3.908 (0.4), 3.378 (18.5), 3.373 (24.4), 3.369 (23.9); 3.3 64 (40.1); 3.361 (34.2); 3.358 (48.4); 3.355 (65.3); 3.054 (1, 9); 2.624 (0.4) 2.530 (0.7), 2.527 (0, 7), 2.515 (47.8), 2.512 (66.8), 2.509 (49.4), 2.396 (0.4), 1.495 (0.4 1, 362 (0.8), 1, 267 (0.4), 1, 2, 36 (0.4), 0.993 (5.6), 0.008 (0.3)
Beispiel No. A12-5: 1H-NMR (600 MHz, de-DMSO δ, ppm) Example No. A12-5: 1 H-NMR (600 MHz, de-DMSO δ, ppm)
7,833(1 ,3);7,663(2,9);7,577(0,7);7,475(1 ,9);7,462(1 ,4);7,258(0,4);4,993(0,4);4,975(0,5) ;4,733(0,5);4,713(0,4);4,001 (0,4);3,931 (16,0);3,917(0,6);3,909(0,3);3,395(2,4);3,372(1 3,5);3,363(19,6);3,357(18,7);3,354(25,1 );3,352(26,5);3,332(0,6);3,1 12(1 ,7);2,899(0,4); 2,530(0,4);2,527(0,4);2,515(34,1 );2,512(46,3);2,509(34,1 );1 ,508(1 ,6);1 ,493(0,4);1 ,350( 0,8);1 ,307(0,5);1 ,295(0,4);0,981 (5,1 );0,008(0,4)  7.833 (1, 3); 7.663 (2.9); 7.577 (0.7); 7.475 (1, 9); 7.462 (1, 4); 7.258 (0.4); 4.993 (0.4); 4.975 (0.5), 4.733 (0.5), 4.713 (0.4), 4.001 (0.4), 3.931 (16.0), 3.917 (0.6), 3.909 (0.3), 3.395 ( 2.4), 3.372 (1 3.5), 3.363 (19.6), 3.357 (18.7), 3.354 (25.1), 3.352 (26.5), 3.332 (0.6), 3, 1 12 (1, 7); 2,899 (0.4); 2.530 (0.4), 2.527 (0.4), 2.515 (34.1), 2.512 (46.3), 2.509 (34.1), 1, 508 (1, 6), 1, 493 (0, 4); 1, 350 (0.8); 1, 307 (0.5); 1, 295 (0.4); 0.981 (5.1); 0.008 (0.4)
Beispiel No. A12-612: 1H-NMR (600 MHz, de-DMSO δ, ppm) Example No. A12-612: 1 H-NMR (600 MHz, de-DMSO δ, ppm)
7,832(1 ,5);7,472(1 ,9);7,459(2,2);7,427(1 ,8);7,415(2,1 );7,400(0,6);7,385(0,8);7,336(1 ,1 ) ;7,324(2,1 );7,307(2,4);7,294(2,6);7,282(1 ,2);7,247(0,4);7,236(0,4);3,980(0,4);3,938(16, 0);3,917(1 ,7);3,909(1 ,0);3,822(1 ,0);3,650(0,8);3,644(0,8);3,370(29,3);3,366(27,4);3,36 1 (52,1 );3,357(44,2);3,355(38,7);3,353(40,8);3,120(0,5);3,096(1 ,0);3,082(1 ,2);3,070(1 ,0 );3,047(13,3);3,030(2,0);3,006(0,6);2,899(0,9);2,739(0,8);2,624(0,4);2,620(0,4);2,533(0 ,6);2,530(0,8);2,527(0,8);2,515(65,4);2,512(89,3);2,509(65,0);2,396(0,5);1 ,462(0,3);1 ,3 94(2,1 );1 ,305(0,5);1 ,265(0,6);1 ,199(8,4);0,008(0,6) 7.832 (1, 5), 7.472 (1, 9), 7.459 (2.2), 7.427 (1, 8), 7.415 (2.1), 7.400 (0.6), 7.385 (0.8), 7.366 (1, 1); 7,324 (2,1); 7,307 (2,4); 7,294 (2,6); 7,282 (1,2); 7,247 (0,4); 7,236 (0,4); 3,980 ( 3.938 (1, 7); 3.909 (1, 0); 3.822 (1, 0); 3.650 (0.8); 3.644 (0.8); 3.370 (29 , 3); 3.366 (27.4); 3.36 1 (52.1); 3.357 (44.2); 3.355 (38.7); 3.353 (40.8); 3.120 (0.5); 3.096 (1, 0); 3.082 (1, 2); 3.070 (1, 0); 3.047 (13.3); 3.030 (2.0); 3.006 (0.6); 2.899 (0.9); 2.739 ( 0.8), 2.624 (0.4), 2.620 (0.4), 2.533 (0, 6), 2.530 (0.8), 2.527 (0.8), 2.515 (65.4), 2.512 (89 , 3); 2.509 (65.0); 2.396 (0.5); 1, 462 (0.3); 1, 3, 94 (2.1); 1, 305 (0.5); 1, 265 ( 0.6); 1, 199 (8.4); 0.008 (0.6)
Beispiel No. A12-615: 1H-NMR (600 MHz, de-DMSO δ, ppm) Example No. A12-615: 1 H-NMR (600 MHz, de-DMSO δ, ppm)
7,961 (0,6);7,837(1 ,2);7,629(2,4);7,488(0,4);7,471 (2,0);7,457(2,9);7,418(1 ,7);7,405(1 ,2) ;7,276(0,5);7,187(0,3);3,936(16,0);3,917(0,6);3,908(0,6);3,899(0,4);3,845(0,4);3,838(0, 6);3,824(1 ,0);3,816(0,8);3,809(0,7);3,800(0,6);3,651 (0,6);3,638(0,8);3,626(0,8);3,616(0 ,7);3,601 (0,4);3,379(9,5);3,373(24,4);3,371 (26,0);3,364(37,6);3,359(74,0);3,106(0,4);3, 059(13,2);3,032(1 ,2);3,025(1 ,2);3,017(1 ,2);3,009(1 ,2);2,994(0,5);2,985(0,4);2,899(3,3); 2,739(3,0);2,623(0,3);2,530(0,4);2,515(38,0);2,512(52,3);2,509(39,0);1 , 388(1 ,7);1 ,349( 0,8);1 ,323(0,7);1 ,270(0,4);1 ,264(0,5);1 ,190(6,7);1 ,135(0,5);1 ,083(0,4)  7.961 (0.6), 7.837 (1.2), 7.629 (2.4), 7.488 (0.4), 7.471 (2.0), 7.457 (2.9), 7.418 (1, 7), 7.405 (1,2), 7,276 (0.5), 7.187 (0.3), 3.936 (16.0), 3.917 (0.6), 3.908 (0.6), 3.899 (0.4), 3.845 ( 3.838 (0.6), 3.681 (0.6), 3.838 (0, 6), 3.824 (1.0), 3.816 (0.8), 3.809 (0.7), 3.800 (0.6), 3.651 (0.6), 3.638 (0 , 3,626 (0.8), 3,616 (0, 7), 3,601 (0,4), 3,379 (9,5), 3,373 (24,4), 3,371 (26,0), 3,364 (37, 6), 3.359 (74.0), 3.106 (0.4), 3.059 (13.2), 3.032 (1.2), 3.025 (1.2), 3.017 (1.2), 3.009 (1 , 2), 2,994 (0.5); 2,985 (0.4); 2,899 (3.3); 2,739 (3.0), 2.623 (0.3), 2.530 (0.4), 2.515 (38.0), 2.512 (52.3), 2.509 (39.0), 1.388 (1, 7) 1, 349 (0.8); 1, 323 (0.7); 1, 270 (0.4); 1, 264 (0.5); 1, 190 (6.7); 1, 135 ( 0.5); 1, 083 (0.4)
Beispiel No. A13-1 : 1H-NMR (400 MHz, de-DMSO δ, ppm) Example No. A13-1: 1 H-NMR (400 MHz, de-DMSO δ, ppm)
7,51 1 (1 ,7);7,490(3,1 );7,483(3,3);7,468(4,3);7,396(2,0);7,379(7,3);7,370(6,8);7,361 (5,4) ;7,344(1 ,2);7,154(0,6);7,021 (1 ,1 );6,886(0,6);4,901 (1 ,1 );4,867(1 ,3);4,791 (0,7);4,754(0,5 );3,773(16,0);3,309(24,7);2,864(2,4);2,690(2,5);2,675(1 ,5);2,670(1 ,5);2,641 (0,9);2,551 ( 0,5);2,547(0,5);2,510(24,6);2,505(47,4);2,501 (63,1 );2,496(47,0);2,492(24,9);2,332(0,4) ;2,328(0,5);2,323(0,4);1 ,381 (2,0);1 ,285(7,0);1 ,237(2,5);1 ,136(7,2);0,000(2,6) 7.51 (1, 7), 7.490 (3.1), 7.483 (3.3), 7.468 (4.3), 7.396 (2.0), 7.379 (7.3), 7.370 (6.8) 7,361 (5.4) 7.344 (1, 2), 7.154 (0.6), 7.021 (1, 1), 6.886 (0.6), 4.901 (1, 1), 4.867 (1, 3), 4.791 (0.7); 4.754 (0.5), 3.773 (16.0), 3.309 (24.7), 2.864 (2.4), 2.690 (2.5), 2.675 (1.5), 2.670 (1.5), 2.641 (0.9), 2.551 (0.5), 2.547 (0.5), 2.510 (24.6), 2.505 (47.4), 2.501 (63.1), 2.496 (47.0), 2.492 ( 24.9); 2.332 (0.4); 2.328 (0.5); 2.233 (0.4); 1, 381 (2.0); 1, 285 (7.0); 1, 237 (2, 5); 1, 136 (7,2); 0,000 (2,6)
Beispiel No. A13-5: 1H-NMR (600 MHz, de-DMSO δ, ppm) Example No. A13-5: 1 H-NMR (600 MHz, de-DMSO δ, ppm)
7,961 (0,5);7,709(0,4);7,675(4,8);7,566(1 ,1 );7,529(0,5);7,486(3,5);7,483(3,5);7,473(2,7) ;7,133(0,4);7,044(0,6);7,006(0,6);6,958(0,4);6,240(0,7);4,913(0,8);4,862(0,4);4,839(1 ,0 );4,800(0,8);4,777(0,4);3,810(2,1 );3,781 (16,0);3,368(29,8);3,364(34,7);3,359(52,7);3,3 55(76,0);3,332(1 ,5);2,954(3,0);2,899(3,0);2,841 (0,4);2,804(0,4);2,748(2,4);2,739(3,2);2 ,71 1 (0,4);2,624(0,4);2,529(0,8);2,515(52,6);2,512(72,2);2,509(53,2);2,396(0,4);1 ,508(4 ,5);1 ,445(0,4);1 ,378(1 ,7);1 ,351 (2,0);1 ,306(1 ,0);1 ,273(6,2);1 ,236(0,9);1 ,1 10(8,5);0,007( 0,4) Beispiel No. A13-612: 1H-NMR (600 MHz, de-DMSO δ, ppm) 7.961 (0.5), 7.709 (0.4), 7.675 (4.8), 7.566 (1, 1), 7.529 (0.5), 7.486 (3.5), 7.483 (3.5), 7.473 (2.7); 7.133 (0.4); 7.044 (0.6); 7.006 (0.6); 6.958 (0.4); 6.240 (0.7); 4.913 (0.8); 0.4), 4.839 (1.0), 4.800 (0.8), 4.777 (0.4), 3.810 (2.1), 3.781 (16.0), 3.368 (29.8), 3.364 (34 , 7), 3.359 (52.7), 3.3 55 (76.0), 3.332 (1.5), 2.954 (3.0), 2.899 (3.0), 2.841 (0.4), 2.804 (0.4); 2.748 (2.4); 2.739 (3.2); 2, 71 1 (0.4); 2.624 (0.4); 2.529 (0.8); 2.515 (52.6) 2.512 (72.2); 2.509 (53.2); 2.396 (0.4); 1, 508 (4, 5); 1, 445 (0.4); 1, 378 (1, 7); 1 , 351 (2.0); 1, 306 (1, 0); 1, 273 (6.2); 1, 236 (0.9); 1, 10 (8.5); 0.007 (0.4 ) Example No. A13-612: 1 H-NMR (600 MHz, de-DMSO δ, ppm)
7,475(1 ,6);7,463(1 ,8);7,421 (1 ,8);7,41 1 (2,1 );7,387(0,6);7,360(0,6);7,352(0,7);7,338(0,8) ;7,328(1 ,6);7,313(2,2);7,297(1 ,7);7,288(1 ,3);7,050(0,5);6,961 (0,7);6,870(0,3);6,242(0,6 );3,917(0,5);3,893(1 ,0);3,885(0,7);3,878(0,7);3,870(0,5);3,787(16,0);3,762(0,6);3,705(0 ,4);3,691 (0,5);3,666(0,5);3,599(0,5);3,583(0,8);3,575(0,7);3,571 (0,8);3,563(0,7);3,560( 0,7);3,549(0,5);3,427(0,3);3,420(0,4);3,413(0,4);3,409(0,5);3,393(2,0);3,371 (1004,2);3, 337(0,5);3,326(0,4);3,131 (0,3);3,1 1 1 (0,7);3,095(1 ,0);3,083(0,7);3,070(0,4);3,060(0,8);3 ,036(1 ,9);3,027(4,1 );3,002(0,4);2,940(0,7);2,921 (0,4);2,900(2,1 );2,889(5,4);2,740(0,7); 2,624(0,6);2,534(1 ,2);2,530(1 ,3);2,528(1 ,3);2,516(104,9);2,513(143,8);2,510(105,2);2, 477(0,3);2,397(0,8);1 ,466(0,8);1 ,445(0,5);1 ,428(0,4);1 ,397(8,7);1 ,377(1 ,2);1 ,306(6,9);1 ,243(0,8);0,862(0,4);0,008(0,5)  7,475 (1,6); 7,463 (1, 8); 7,421 (1, 8); 7,41 1 (2,1); 7,387 (0,6); 7,360 (0,6); 7,352 (0,7 7.383 (0.8), 7.328 (1, 6), 7.313 (2.2), 7.297 (1, 7), 7.288 (1, 3), 7.050 (0.5), 6.961 (0.7) 6.870 (0.3), 6.242 (0.6), 3.917 (0.5), 3.893 (1.0), 3.885 (0.7), 3.878 (0.7), 3.870 (0.5); 3.787 (16.0), 3.762 (0.6), 3.705 (0.4), 3.691 (0.5), 3.666 (0.5), 3.599 (0.5), 3.583 (0.8), 3.575 (0.7), 3.571 (0.8), 3.563 (0.7), 3.560 (0.7), 3.549 (0.5), 3.427 (0.3), 3.420 (0.4), 3.413 ( 0.4); 3.409 (0.5); 3.393 (2.0); 3.371 (1004.2); 3, 337 (0.5); 3.326 (0.4); 3.113 (0.3); 3 , 1 1 1 (0.7), 3.095 (1, 0), 3.083 (0.7), 3.070 (0.4), 3.060 (0.8), 3.036 (1.9), 3.027 (4 , 1), 3.002 (0.4), 2.940 (0.7), 2.921 (0.4), 2.900 (2.1), 2.889 (5.4), 2.740 (0.7); 2.624 (0.6), 2.534 (1, 2), 2.530 (1.3), 2.528 (1.3), 2.516 (104.9), 2.513 (143.8), 2.510 (105.2), 2 , 477 (0.3); 2.397 (0.8); 1, 466 (0.8); 1, 445 (0.5); 1, 428 (0.4); 1, 397 (8.7) 1, 377 (1, 2); 1, 306 (6.9); 1, 243 (0.8); 0.862 (0.4); 0.008 (0.5)
Beispiel No. A13-615: 1H-NMR (600 MHz, de-DMSO δ, ppm) Example No. A13-615: 1 H-NMR (600 MHz, de-DMSO δ, ppm)
7,961 (0,4);7,632(2,7);7,588(0,9);7,468(1 ,6);7,454(2,5);7,419(1 ,9);7,406(1 ,5);7,393(1 ,5) ;7,044(0,5);6,957(0,7);6,244(0,5);3,888(0,8);3,786(16,0);3,756(0,6);3,698(0,5);3,662(0, 5);3,651 (0,4);3,577(0,7);3,382(17,7);3,376(23,7);3,366(41 ,5);3,364(20,5);3,360(24,8);3 ,357(40,9);3,353(36,2);3,094(0,9);3,080(1 ,1 );3,021 (4,3);2,970(0,9);2,922(5,7);2,899(3, 0);2,739(2,5);2,623(0,3);2,515(45,7);2,512(61 ,9);2,509(46,2);2,396(0,4);1 ,462(0,9);1 ,4 45(0,6);1 ,424(0,8);1 ,389(8,8);1 ,348(2,2);1 ,299(6,6);0,007(0,4) Beispiel No. A14-1 : 1H-NMR (600 MHz, de-DMSO δ, ppm) 7.961 (0.4), 7.632 (2.7), 7.588 (0.9), 7.468 (1, 6), 7.454 (2.5), 7.419 (1.9), 7.406 (1.5), 7.393 (1, 5); 7.044 (0.5); 6.957 (0.7); 6.244 (0.5); 3.888 (0.8); 3.786 (16.0); 3.756 (0.6); 3.698 ( 3.652 (0.5), 3.652 (0.5), 3.651 (0.4), 3.577 (0.7), 3.382 (17.7), 3.376 (23.7), 3.366 (41, 5), 3.364 (20 , 3,360 (24.8); 3, 357 (40.9); 3.353 (36.2); 3.094 (0.9); 3.080 (1, 1); 3.021 (4.3); 2.970 (3) 2.922 (5.7), 2.899 (3, 0), 2.739 (2.5), 2.623 (0.3), 2.515 (45.7), 2.512 (61, 9), 2.509 (46 , 2); 2.396 (0.4); 1, 462 (0.9); 1.445 (0.6); 1, 424 (0.8); 1, 389 (8.8); 1, 348 (2.2); 1, 299 (6.6); 0.007 (0.4) Example No. A14-1: 1 H-NMR (600 MHz, de-DMSO δ, ppm)
7,519(0,5);7,512(0,7);7,504(0,9);7,469(0,8);7,456(0,9);7,404(1 ,3);7,397(1 ,6);7,393(1 ,7) ;7,385(1 ,3);7,382(1 ,3);7,370(1 ,1 );7,358(0,7);7,076(0,6);6,987(0,3);4,810(0,8);4,787(1 ,3 );4,713(1 ,1 );4,689(0,7);3,925(5,6);3,915(0,9);3,882(3,8);3,378(9,3);3,373(8,9);3,366(17 ,2);3,361 (12,9);3,358(19,0);3,354(25,9);2,899(1 ,0);2,792(5,9);2,739(0,9);2,662(1 ,2);2,5 18(9,5);2,515(21 ,2);2,512(29,6);2,509(21 ,6);2,506(10,1 );1 ,512(0,4);1 ,396(2,1 );1 ,297(5, 2);1 , 237(16,0) Beispiel No. A14-5: 1H-NMR (600 MHz, de-DMSO δ, ppm) 7.519 (0.5), 7.512 (0.7), 7.504 (0.9), 7.469 (0.8), 7.456 (0.9), 7.404 (1.3), 7.397 (1, 6), 7.393 (1, 7); 7,385 (1,3), 7,382 (1,3), 7,370 (1,1), 7,358 (0,7), 7,076 (0,6), 6,987 (0,3), 4,810 ( 4,787 (1, 3); 4,787 (1, 1); 4,689 (0,7); 3,925 (5,6); 3,915 (0,9); 3,882 (3,8); 3,378 (9 3,373 (8,9); 3,366 (17,2); 3,361 (12,9); 3,358 (19,0); 3,354 (25,9); 2,899 (1, 0); 2,792 (5); 9), 2,739 (0.9), 2,662 (1,2), 2,5,18 (9,5), 2,515 (21, 2), 2,512 (29,6), 2,509 (21, 6), 2,506 ( 10.1); 1, 512 (0.4); 1, 396 (2.1); 1, 297 (5, 2); 1, 237 (16.0) A14-5: 1 H-NMR (600 MHz, de-DMSO δ, ppm)
17,528(0,6);13,061 (0,7);1 1 ,206(0,7);7,701 (1 ,0);7,659(1 ,5);7,533(1 ,2);7,512(1 ,1 );7,488( 1 ,0);7,475(1 ,2);7,425(1 ,3);7,41 1 (1 ,3);7,079(0,8);4,801 (0,8);4,778(1 ,4);4,686(1 ,3);4,663 (0,9);3,923(6,2);3,912(1 ,3);3,898(0,8);3,889(1 ,2);3,881 (3,6);3,461 (0,9);3,365(173,7);3, 362(167,0);3,356(223,6);3,355(242,3);3,351 (291 ,3);3,332(1 ,5);2,900(0,8);2,839(5,5);2, 755(0,8);2,740(1 ,8);2,726(0,7);2,623(3,2);2,530(5,6);2,526(6,1 );2,515(395,2);2,512(54 0,5);2,509(394,0);2,454(0,8);2,414(0,7);2,396(3,1 );1 ,509(3,5);1 ,377(1 ,9);1 ,358(0,7);1 ,2 78(4,7);1 ,242(0,9);1 ,223(16,0);0,009(3,9)  17.528 (0.6); 13.061 (0.7); 1 1, 206 (0.7); 7.701 (1, 0); 7.659 (1, 5); 7.533 (1, 2); 7.512 (1, 1 7,488 (1, 0), 7,475 (1,2), 7,425 (1,3), 7,41 1 (1,3), 7,079 (0,8), 4,801 (0,8), 4,778 (1 , 4), 4,686 (1,3), 4,663 (0,9), 3,923 (6,2), 3,912 (1,3), 3,898 (0,8), 3,889 (1,2), 3,881 (3, 6), 3.461 (0.9), 3.365 (173.7), 3, 362 (167.0), 3.356 (223.6), 3.355 (242.3), 3.351 (291, 3), 3.332 (1 2.900 (0.8), 2.839 (5.5), 2.755 (0.8), 2.740 (1.8), 2.726 (0.7), 2.623 (3.2), 2.530 (2) 5.6), 2.526 (6.1), 2.515 (395.2), 2.512 (54.5), 2.509 (394.0), 2.454 (0.8), 2.414 (0.7), 2.396 ( 3.1); 1, 509 (3.5); 1, 377 (1, 9); 1, 358 (0.7); 1, 2 78 (4.7); 1, 242 (0.9) 1, 223 (16.0), 0.009 (3.9)
Beispiel No. A14-612: 1H-NMR (600 MHz, de-DMSO δ, ppm) Example No. A14-612: 1 H-NMR (600 MHz, de-DMSO δ, ppm)
7,400(0,8);7,397(0,6);7,389(0,9);7,385(0,9);7,337(0,6);7,333(0,7);7,322(0,9);7,290(0,5) ;7,281 (0,9);7,278(0,9);7,275(1 ,0);7,270(1 ,4);7,266(0,8);7,263(0,8);7,259(0,7);7,121 (0,3 );7,032(0,8);6,943(0,4);3,888(5,9);3,883(2,5);3,581 (0,7);3,568(0,9);3,553(0,7);3,370(7, 6);3,365(8,8);3,361 (1 1 ,4);3,358(13,1 );3,354(19,2);3,1 1 1 (0,5);3,038(5,8);3,019(0,7);3,0 1 1 (0,7);3,004(0,5);2,999(0,5);2,899(1 ,1 );2,739(0,6);2,518(7,8);2,515(17,5);2,512(24,7); 2,509(18,2);2,506(8,5);1 ,479(1 ,3);1 ,426(16,0);1 ,404(0,4);1 ,380(0,5);1 ,343(1 ,1 );1 ,323(0 .6) 7,400 (0.8); 7,397 (0.6); 7,389 (0.9); 7,385 (0.9); 7,337 (0.6); 7,333 (0.7); 7,322 (0.9); 7,290 (0.5); 7.281 (0.9); 7.278 (0.9); 7.275 (1, 0); 7.270 (1, 4); 7.266 (0.8); 7.263 (0.8); 7.259 (7) 0.7), 7.121 (0.3), 7.032 (0.8), 6.943 (0.4), 3.888 (5.9), 3.883 (2.5), 3.581 (0.7), 3.568 (0 , 9), 3.553 (0.7), 3.370 (7, 6), 3.365 (8.8), 3.361 (1 1, 4), 3.358 (13.1), 3.354 (19.2), 3.1 1 1 (0.5), 3.038 (5.8), 3.019 (0.7), 3.0 1 1 (0.7), 3.004 (0.5), 2.999 (0.5), 2.899 (1 , 1), 2,739 (0.6), 2.518 (7.8), 2.515 (17.5), 2.512 (24.7); 2.509 (18.2), 2.506 (8.5), 1.479 (1, 3), 1.426 (16.0), 1.404 (0.4), 1.80 (0.5); 1, 343 (1, 1); 1, 323 (0 .6)
Beispiel No. A14-615: 1H-NMR (600 MHz, de-DMSO δ, ppm) Example No. A14-615: 1 H-NMR (600 MHz, de-DMSO δ, ppm)
7,961 (0,4);7,635(0,4);7,566(1 ,5);7,477(0,3);7,375(3,4);7,120(0,4);7,031 (0,8);6,942(0,4) ;3,909(0,3);3,885(6,0);3,880(2,8);3,579(0,4);3,575(0,6);3,568(0,7);3,560(0,7);3,552(0,5 );3,548(0,5);3,367(8,4);3,361 (10,7);3,358(14,9);3,356(14,6);3,353(22,3);3,099(0,6);3,0 29(5,7);3,014(0,9);3,001 (1 ,2);2,987(0,7);2,931 (0,5);2,899(2,9);2,739(2,4);2,530(0,3);2, 527(0,4);2,518(10,2);2,515(22,4);2,512(31 ,1 );2,509(22,4);2,506(10,0);1 ,473(1 ,3);1 ,419 (16,0);1 ,403(0,5);1 ,389(0,4);1 ,338(1 ,2);1 ,223(0,5) 7.961 (0.4), 7.635 (0.4), 7.566 (1.5), 7.477 (0.3), 7.375 (3.4), 7.120 (0.4), 7.031 (0.8), 6.942 (0.4); 3.909 (0.3); 3.885 (6.0); 3.880 (2.8); 3.579 (0.4); 3.575 (0.6); 3.568 (0.7); 3.560 ( 3.5) (0.5), 3.548 (0.5), 3.367 (8.4), 3.361 (10.7), 3.358 (14.9), 3.356 (14.6), 3.353 (22 , 3), 3.099 (0.6), 3.0 29 (5.7), 3.014 (0.9), 3.001 (1, 2), 2.987 (0.7), 2.931 (0.5), 2.899 (2.9); 2,739 (2.4); 2,530 (0.3); 2, 527 (0.4), 2.518 (10.2), 2.515 (22.4), 2.512 (31, 1), 2.509 (22.4), 2.506 (10.0), 1, 473 (1, 3) 1, 419 (16.0); 1, 403 (0.5); 1, 389 (0.4); 1, 338 (1, 2); 1, 223 (0.5)
Beispiel No. A19-13: 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. A19-13: 1 H-NMR (400 MHz, CDCls δ, ppm)
7,544(0,9);7,528(1 ,1 );7,522(2,3);7,506(1 ,9);7,501 (1 ,5);7,485(1 ,3);7,263(90,9);7,208(3, 1 );7,071 (6,7);6,999(0,5);6,935(3,5);6,904(0,9);6,902(0,8);6,898(1 ,2);6,896(1 ,3);6,882(2 ,5);6,877(5,0);6,860(1 ,6);6,856(5,8);6,850(1 ,3);6,834(1 ,7);6,828(1 ,2);5,156(8,7);5,154( 8,7);4,154(1 ,3);4,145(1 ,4);4,131 (1 ,9);4,121 (1 ,4);4,1 12(1 ,4);3,861 (0,8);3,759(14,9);3,75 7(16,0);3,364(0,8);3,360(0,8);3,343(1 ,9);3,330(1 ,7);3,321 (1 ,5);3,316(1 ,8);3,301 (0,8);3, 294(0,8);2,956(1 ,2);2,884(1 ,1 );2,883(1 ,0);2,309(0,7);2,302(1 ,1 );2,295(1 ,1 );2,286(1 ,8);2 ,274(1 ,7);2,269(2,0);2,256(1 ,1 );2,088(0,7);2,075(1 ,3);2,071 (1 ,7);2,063(1 ,5);2,054(2,6); 2,051 (2,4);2,044(2,3);2,036(1 ,4);1 ,600(3,5);1 ,285(0,6);1 ,259(0,8);0,008(1 ,1 );0,000(35, 0);-0,009(1 ,0) Beispiel No. A19-61 : 1H-NMR (400 MHz, CDCIs δ, ppm) 7,544 (0.9); 7.528 (1, 1); 7,522 (2,3); 7,506 (1,9); 7,501 (1,5); 7,485 (1,3); 7,263 (90,9); 7,208 (3, 1); 7.071 (6.7); 6.999 (0.5); 6.935 (3.5); 6.904 (0.9); 6.902 (0.8); 6.898 (1, 2); 1, 3), 6,882 (2,5), 6,877 (5,0), 6,860 (1,6), 6,856 (5,8), 6,850 (1,3), 6,834 (1, 7), 6,828 (1 , 2), 5,156 (8,7), 5,154 (8,7), 4,154 (1,3), 4,145 (1,4), 4,131 (1, 9), 4,121 (1,4), 4,112 (1, 4); 3,861 (0.8); 3,759 (14.9); 3,75 7 (16,0); 3,364 (0.8); 3,360 (0.8); 3,343 (1, 9) 3,330 (1, 7), 3,321 (1, 5), 3,316 (1, 8), 3,301 (0,8), 3, 294 (0,8), 2,956 (1,2), 2,884 (1, 1 2.883 (1, 0); 2.309 (0.7); 2.302 (1, 1); 2.295 (1, 1); 2.286 (1, 8); 2, 274 (1, 7); 2.269 (2, 2), 2.256 (1, 1), 2.088 (0.7), 2.075 (1, 3), 2.071 (1, 7), 2.063 (1, 5), 2.054 (2.6); 2.051 (2.4); 2.044 (2.3); 2.036 (1, 4); 1, 600 (3.5); 1, 285 (0.6); 1, 259 (0.8); 0.008 (0.008) 1, 1); 0.000 (35, 0); - 0.009 (1, 0) Example no. A19-61: 1 H-NMR (400 MHz, CDCIs δ, ppm)
8,019(0,8);7,755(2,1 );7,735(2,7);7,728(2,3);7,725(2,3);7,708(2,6);7,705(2,6);7,615(1 ,2) ;7,61 1 (1 ,2);7,596(2,5);7,592(2,3);7,576(1 ,5);7,573(1 ,3);7,534(1 ,8);7,532(1 ,8);7,520(1 ,4  8.019 (0.8), 7.755 (2.1), 7.735 (2.7), 7.728 (2.3), 7.725 (2.3), 7.708 (2.6), 7.705 (2.6), 7.615 (1, 2); 7.61 1 (1, 2); 7.596 (2.5); 7.592 (2.3); 7.576 (1, 5); 7.573 (1, 3); 7.534 (1, 8) 7.532 (1, 8); 7.520 (1, 4
0,5);7,274(0,6);7,2734(0,7);7,2726(0,7);7,272(0,8);7,271 (0,9);7,270(1 ,1 );7,2694(1 ,3);7, 2686(1 ,4);7,268(1 ,5);7,267(1 ,8);7,266(2,4);7,2654(2,9);7,2645(4,1 );7,261 (179,9);7,257 (2,0);7,2564(1 ,2);7,2555(1 ,0);7,255(0,8);7,254(0,5);7,21 1 (1 ,6);7,190(1 ,4);7,053(3,0);6, 997(1 ,0);6,916(1 ,5);5,363(9,9);4,172(1 ,6);4,149(1 ,4);4,131 (0,9);4,1 13(0,8);3,765(16,0); 3,465(1 ,5);3,440(1 ,5);2,9564(8,5);2,9557(8,7);2,885(7,5);2,883(7,6);2,299(1 ,7);2,282(1 ,7);2,170(0,7);2,129(2,5);2,1 1 1 (1 ,1 );2,080(3,4);2,044(3,6);1 ,568(6,1 );1 ,277(1 ,1 );1 ,259( 2,3);1 ,241 (1 ,1 );0,008(2,2);0,000(82,7);-0,009(2,3);-0,050(0,6) 7,274 (0.6); 7.2734 (0.7); 7.2726 (0.7); 7.272 (0.8); 7.271 (0.9); 7.270 (1, 1) 7,26694 (1, 3); 7, 2686 (1, 4); 7,268 (1, 5); 7,267 (1, 8); 7,266 (2,4); 7,2654 (2,9); 7 , 2645 (4.1), 7.261 (179.9), 7.257 (2.0), 7.2564 (1, 2), 7.2555 (1.0), 7.255 (0.8), 7.254 (0 , 5), 7,21 1 (1,6), 7,190 (1,4), 7,053 (3,0), 6, 997 (1, 0), 6,916 (1,5), 5,363 (9,9) 4,172 (1,6), 4,149 (1,4), 4,131 (0,9), 4,113 (0,8), 3,765 (16,0); 3,465 (1, 5); 3,440 (1, 5); 2,9564 (8,5); 2,9557 (8,7); 2,885 (7,5); 2,883 (7,6); 2,299 (1, 7), 2.282 (1, 7), 2.170 (0.7), 2.129 (2.5), 2.1 1 1 (1, 1), 2.080 (3.4), 2.044 (3.6), 1 , 568 (6.1); 1, 277 (1, 1); 1, 259 (2, 3); 1, 241 (1, 1); 0.008 (2.2); 0.000 (82.7); 0.009 (2.3) - 0.050 (0.6)
Beispiel No. A20-94: 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. A20-94: 1 H-NMR (400 MHz, CDCIs δ, ppm)
8,520(3,6);8,439(2,6);8,433(2,7);7,774(1 ,7);7,768(1 ,7);7,754(1 ,9);7,747(1 ,9);7,519(0,7) ;7,454(3,1 );7,433(2,7);7,260(125,3);7,184(1 ,8);7,049(4,0);6,996(0,7);6,914(2,0);5,246( 8,5);4,814(1 ,0);4,801 (1 ,3);4,788(1 ,2);3,955(0,7);3,934(16,0);3,726(0,6);3,710(1 ,2);3,69 5(1 ,2);3,680(1 ,2);3,665(0,6);2,463(0,6);2,448(1 ,2);2,428(1 ,3);2,416(0,9);2,271 (0,5);2,2 52(1 ,0);2,245(1 ,1 );2,232(1 ,6);2,224(1 ,0);2,217(0,8);1 ,333(0,7);1 ,285(1 ,1 );1 ,256(1 ,7);0, 008(1 ,5);0,000(53,8);-0,009(2,3) Beispiel No. A21 -1 : 1H-NMR (400 MHz, de-DMSO δ, ppm) 8.520 (3.6), 8.439 (2.6), 8.433 (2.7), 7.744 (1, 7), 7.768 (1, 7), 7.754 (1, 9), 7.747 (1, 9), 7.519 (0.7); 7.454 (3.1); 7.433 (2.7); 7.260 (125.3); 7.184 (1, 8); 7.049 (4.0); 6.996 (0.7); 6.914 ( 2.0), 5.246 (8.5), 4.814 (1, 0), 4.801 (1.3), 4.788 (1.2), 3.955 (0.7), 3.934 (16.0), 3.726 (0 , 6); 3.710 (1, 2); 3.69 5 (1, 2); 3.680 (1, 2); 3.665 (0.6); 2.463 (0.6); 2.448 (1, 2); 2.428 (1, 3); 2.416 (0.9); 2.271 (0.5); 2.2 52 (1, 0); 2.245 (1, 1); 2.232 (1, 6); 2.224 (1, 0) ; 2,217 (0,8); 1,333 (0,7); 1, 285 (1,1); 1, 256 (1, 7); 0, 008 (1, 5); 0,000 (53,8) ; -0.009 (2.3) Example No. A21 -1: 1 H-NMR (400 MHz, de-DMSO δ, ppm)
8,501 (1 ,8);7,485(2,0);7,480(1 ,4);7,475(1 ,3);7,468(1 ,9);7,462(3,0);7,343(0,8);7,330(3,4) ;7,325(5,4);7,316(7,3);7,307(5,0);7,302(2,8);7,289(0,7);7,283(0,3);7,233(2,0);7,224(1 ,7 );7,216(1 ,2);7,210(1 ,4);7,186(0,7);5,105(1 ,0);5,094(1 ,0);4,838(7,7);3,937(16,0);3,335(2 6,6);2,51 1 (7,3);2,505(20,6);2,503(20,0);2,498(12,9);2,491 (14,3);0,000(2,3)  7.475 (1, 3), 7.468 (1, 9), 7.462 (3.0), 7.343 (0.8), 7.303, 7.475 (1, 4), 7.475 (1, 4), 7.475 (1, 4); (3.4); 7.325 (5.4); 7.316 (7.3); 7.307 (5.0); 7.302 (2.8); 7.289 (0.7); 7.283 (0.3); 7.233 (7). 7.224 (1, 7), 7.216 (1,2), 7,210 (1,4), 7,186 (0,7), 5,105 (1,0), 5,094 (1,0), 4,838 (7 , 7); 3.937 (16.0); 3.335 (2.6.6); 2.51 1 (7.3); 2.555 (20.6); 2.503 (20.0); 2.498 (12.9); 2,491 (14,3); 0,000 (2,3)
Beispiel No. A21 -5: 1H-NMR (400 MHz, de-DMSO δ, ppm) Example No. A21 -5: 1 H-NMR (400 MHz, de-DMSO δ, ppm)
8,492(1 ,6);7,644(3,7);7,639(4,0);7,446(0,6);7,430(2,3);7,425(2,2);7,409(2,8);7,404(2,8) ;7,310(1 ,3);7,254(2,9);7,233(2,3);7,174(0,6);5,144(0,9);5,133(0,9);4,805(7,3);3,933(16, 0);3,329(21 ,3);2,524(0,5);2,51 1 (1 1 ,1 );2,506(22,9);2,502(32,1 );2,498(31 ,5);2,484(1 1 ,2); 0,000(6,0)  8.492 (1, 6), 7.644 (3.7), 7.639 (4.0), 7.446 (0.6), 7.430 (2.3), 7.425 (2.2), 7.409 (2.8), 7.404 (2.8); 7.310 (1, 3); 7.254 (2.9); 7.233 (2.3); 7.174 (0.6); 5.144 (0.9); 5.133 (0.9); 4.805 ( 3.333 (16, 0), 3.329 (21, 3), 2.524 (0.5), 2.51 1 (1 1, 1), 2.506 (22.9), 2.502 (32.1) 2.498 (31, 5); 2.484 (1 1, 2); 0,000 (6.0)
Beispiel No. A22-1 : 1H-NMR (400 MHz, de-DMSO δ, ppm) Example No. A22-1: 1 H-NMR (400 MHz, de-DMSO δ, ppm)
7,497(1 ,7);7,478(2,0);7,372(0,9);7,359(2,9);7,353(3,8);7,344(7,8);7,337(4,9);7,328(3,4) ;7,315(1 ,6);7,308(4,1 );7,300(2,7);7,290(1 ,7);7,284(1 ,8);7,139(2,6);7,003(5,8);6,868(3,0 );5,080(1 ,3);5,069(1 ,3);4,853(5,4);3,791 (16,0);3,318(136,7);3,268(0,7);2,682(0,5);2,67 8(0,7);2,673(0,6);2,531 (3,4);2,517(44,6);2,513(90,9);2,508(124,3);2,504(90,3);2,499(4 5,6);2,423(10,9);2,410(1 1 ,1 );2,345(0,5);2,340(0,7);2,335(0,9);2,331 (0,7) 7.497 (1, 7), 7.478 (2.0), 7.372 (0.9), 7.359 (2.9), 7.353 (3.8), 7.344 (7.8), 7.337 (4.9), 7.328 (3,4); 7,315 (1,6), 7,308 (4,1), 7,300 (2,7), 7,290 (1, 7), 7,284 (1, 8), 7,139 (2,6), 7,003 ( 5.8), 6.868 (3.0), 5.080 (1.3), 5.069 (1.3), 4.853 (5.4), 3.791 (16.0), 3.318 (136.7), 3.268 (0 , 7); 2.682 (0.5); 2.67 8 (0.7); 2.673 (0.6); 2.531 (3.4); 2.517 (44.6); 2.513 (90.9); 2.508 (124.3); 2.504 (90.3); 2.499 (4 5.6); 2.423 (10.9); 2.410 (1 1, 1); 2.345 (0.5); 2.340 (0.7); 2.335 (0.9); 2.331 (0.7)
Beispiel No. A22-5: 1H-NMR (400 MHz, de-DMSO δ, ppm) Example No. A22-5: 1 H-NMR (400 MHz, de-DMSO δ, ppm)
7,650(3,2);7,458(2,9);7,453(2,8);7,437(4,0);7,432(4,0);7,331 (4,5);7,310(3,3);7,128(2,7) ;6,993(5,9);6,858(3,0);5,1 14(1 ,3);5,102(1 ,3);4,820(5,6);3,782(16,0);3,336(40,7);2,891 ( 0,5);2,732(0,4);2,512(7,5);2,508(15,6);2,503(20,9);2,498(15,3);2,494(7,5);2,41 1 (9,3);2, 398(9,3);0,000(3,8)  7.650 (3.2), 7.458 (2.9), 7.453 (2.8), 7.437 (4.0), 7.432 (4.0), 7.331 (4.5), 7.310 (3.3), 7.128 (2,7); 6,993 (5.9); 6,858 (3,0); 5,1 14 (1, 3); 5,102 (1,3); 4,820 (5,6); 3,782 (16,0) 3.366 (40.7), 2.891 (0.5), 2.732 (0.4), 2.512 (7.5), 2.508 (15.6), 2.503 (20.9), 2.498 (15.3); 2.494 (7.5), 2.41 1 (9.3), 2.398 (9.3), 0.000 (3.8)
Beispiel No. A23-1 : 1H-NMR (400 MHz, de-DMSO δ, ppm) Example No. A23-1: 1 H-NMR (400 MHz, de-DMSO δ, ppm)
7,505(1 ,8);7,485(2,3);7,400(1 ,1 );7,383(4,5);7,369(3,5);7,358(2,7);7,352(2,8);7,340(2,3) ;7,334(2,1 );7,323(1 ,2);7,130(2,8);6,994(5,6);6,858(2,6);5,057(0,7);5,043(1 ,9);5,030(1 ,9 );5,017(0,7);4,871 (9,1 );4,617(0,6);3,874(16,0);3,331 (56,2);2,890(0,9);2,731 (0,8);2,524( 0,6);2,51 1 (13,7);2,506(28,3);2,502(37,7);2,497(27,8);2,493(13,7);2,332(8,5);2,319(8,3) ;0,000(7,2) Beispiel No. A23-5: 1H-NMR (400 MHz, de-DMSO δ, ppm) 7.555 (1, 8), 7.485 (2.3), 7.400 (1, 1), 7.383 (4.5), 7.369 (3.5), 7.358 (2.7), 7.352 (2.8), 7.340 (2,3); 7,334 (2,1); 7,323 (1,2); 7,130 (2,8); 6,994 (5,6); 6,858 (2,6); 5,057 (0,7); 5,043 ( 1, 9), 5.030 (1.9), 5.017 (0.7), 4.871 (9.1), 4.617 (0.6), 3.874 (16.0), 3.331 (56.2), 2.890 (0 , 9), 2,731 (0.8), 2.524 (0.6), 2.51 1 (13.7), 2.506 (28.3), 2.502 (37.7), 2.497 (27.8), 2.493 (13.7); 2.332 (8.5); 2.319 (8.3); 0.000 (7.2) Example No. A23-5: 1 H-NMR (400 MHz, de-DMSO δ, ppm)
7,952(0,4);7,665(3,4);7,485(1 ,5);7,464(2,6);7,413(3,5);7,393(2,2);7,1 17(1 ,5);6,981 (3,1 ) ;6,845(1 ,5);5,069(1 ,9);5,055(1 ,9);5,043(0,7);4,846(8,0);4,596(0,5);3,870(16,0);3,328(2 0,7);2,890(2,8);2,731 (2,5);2,506(23,5);2,502(31 ,2);2,498(24,4);2,326(7,6);2,313(7,3);0, 000(4,9)  7.952 (0.4), 7.665 (3.4), 7.485 (1.5), 7.464 (2.6), 7.413 (3.5), 7.393 (2.2), 7.1.17 (1, 5) 6.981 (3.1), 6.845 (1.5), 5.069 (1.9), 5.055 (1.9), 5.043 (0.7), 4.846 (8.0), 4.596 (0.5) 3,870 (16,0), 3,328 (2 0,7), 2,890 (2,8), 2,731 (2,5), 2,506 (23,5), 2,502 (31, 2), 2,498 (24,4) 2,326 (7,6); 2,313 (7,3); 0, 000 (4,9)
Beispiel No. A24-40: 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. A24-40: 1 H-NMR (400 MHz, CDCIs δ, ppm)
8,430(6,7);8,417(6,8);7,521 (0,6);7,464(6,7);7,452(6,4);7,289(2,2);7,271 (0,5);7,270(0,6) ;7,2693(0,7);7,2685(0,8);7,268(1 ,0);7,267(1 ,2);7,266(1 ,6);7,262(96,6);7,258(1 ,4);7,257 (1 ,1 );7,2562(0,8);7,2555(0,7);7,255(0,5);7,212(0,9);7,153(4,7);7,016(2,3);6,998(0,6);5, 494(16,0);4,370(0,9);4,361 (0,9);4,349(1 ,3);4,338(1 ,0);4,328(1 ,0);3,856(0,5);3,755(10,3 );3,753(1 1 ,3);3,628(0,6);3,623(0,7);3,607(1 ,4);3,602(1 ,1 );3,591 (1 ,2);3,585(1 ,1 );3,578(1 ,4);3,563(0,7);3,557(0,6);2,956(1 ,1 );2,885(0,9);2,883(1 ,0);2,287(0,7);2,280(0,7);2,273( 8.430 (6.7); 8.417 (6.8); 7.521 (0.6); 7.464 (6.7); 7.452 (6.4); 7.289 (2.2); 7.271 (0.5); 7.270 (0.6); 7.2693 (0.7); 7.2685 (0.8); 7.268 (1, 0); 7.267 (1, 2); 7.266 (1, 6); 7.262 (96.6 7,258 (1, 4), 7,257 (1,1), 7,2562 (0,8), 7,2555 (0,7), 7,255 (0,5), 7,212 (0,9), 7,153 ( 4.7), 7.016 (2.3), 6.998 (0.6), 5.494 (16.0), 4.370 (0.9), 4.361 (0.9), 4.349 (1, 3), 4.338 (1, 0), 4.328 (1, 0), 3.856 (0.5), 3.755 (10.3), 3.753 (1 1, 3), 3.628 (0.6), 3.623 (0.7), 3.607 (1, 4); 3.602 (1, 1); 3.591 (1, 2); 3.585 (1, 1); 3.578 (1, 4); 3.563 (0.7); 3.557 (0.6); 2.956 ( 1, 1); 2.885 (0.9); 2.883 (1, 0); 2.287 (0.7); 2.280 (0.7); 2.273 (
1 .3) ;2,259(1 ,2);2,255(1 ,5);2,242(0,8);2,074(2,6);1 ,981 (1 ,1 );1 ,964(1 ,8);1 ,961 (1 ,8);1 ,954 (1 ,2);1 ,946(1 ,0);0,008(1 ,1 );0,003(0,5);0,002(1 ,1 );0,000(41 ,4);-0,005(1 ,0);-0,006(0,8);-1. 3), 2.259 (1, 2), 2.255 (1, 5), 2.242 (0.8), 2.074 (2.6), 1, 981 (1, 1), 1, 964 (1, 8) 1, 961 (1, 8), 1, 954 (1, 2), 1, 946 (1, 0), 0.008 (1, 1), 0.003 (0.5), 0.002 (1, 1), 0.000 (41, 4), - 0.005 (1, 0), - 0.006 (0.8), -
0,007(0,7);-0,008(1 ,4) 0.007 (0.7); - 0.008 (1, 4)
Beispiel No. A24-679: 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. A24-679: 1 H-NMR (400 MHz, CDCls δ, ppm)
8,728(4,3);8,724(4,4);8,716(4,6);8,712(4,4);8,095(3,3);8,091 (3,4);8,074(3,6);8,070(3,4) ;7,522(3,9);7,519(2,6);7,51 1 (3,8);7,502(3,6);7,490(3,6);7,31 1 (0,9);7,305(0,6);7,299(0,5 );7,298(0,5);7,292(1 ,1 );7,291 (0,8);7,2884(0,7);7,2876(0,7);7,287(0,7);7,286(0,7);7,285 2(0,7);7,2845(0,8);7,284(0,8);7,283(0,8);7,282(0,9);7,2813(0,8);7,2805(0,8);7,280(0,9); 7,279(1 ,0);7,278(0,9);7,2773(0,9);7,2765(0,9);7,276(1 ,1 );7,275(1 ,2);7,274(1 ,3);7,2733( 8.728 (4.3), 8.724 (4.4), 8.716 (4.6), 8.712 (4.4), 8.095 (3.3), 8.091 (3.4), 8.074 (3.6), 8.070 (3.4), 7.522 (3.9), 7.519 (2.6), 7.51 (3.8), 7.502 (3.6), 7.490 (3.6), 7.31 (0 , 9), 7.305 (0.6), 7.299 (0.5), 7.298 (0.5), 7.292 (1, 1), 7.291 (0.8), 7.2884 (0.7), 7, 2876 (0.7), 7.287 (0.7), 7.286 (0.7), 7.285 2 (0.7), 7.2845 (0.8), 7.284 (0.8), 7.283 (0.8 ); 7.282 (0.9); 7.2813 (0.8) 7.2805 (0.8); 7,280 (0.9); 7.279 (1, 0), 7.278 (0.9), 7.2773 (0.9), 7.2765 (0.9), 7.276 (1, 1), 7.275 (1, 2), 7.274 (1, 3) 7.2733 (
1 .4) ;7,2725(1 ,5);7,272(1 ,7);7,271 (2,0);7,270(2,3);7,2693(2,7);7,2686(3,2);7,268(3,3);7, 267(3,8);7,266(4,4);7,2653(5,5);7,2645(6,8);7,264(9,0);7,260(391 ,9);7,257(8,1 );7,25637,2725 (1, 5), 7,272 (1, 7), 7,271 (2,0), 7,270 (2,3), 7,2693 (2,7), 7,2686 (3, 2), 7.268 (3.3), 7, 267 (3.8), 7.266 (4.4), 7.2653 (5.5), 7.2645 (6.8), 7.264 (9.0) 7,260 (391,9); 7,257 (8,1); 7,2563
(5,4);7,2555(4,1 );7,255(3,6);7,254(3,0);7,253(2,5);7,2523(1 ,7);7,2515(1 ,5);7,251 (1 ,4);7 ,250(1 ,2);7,249(1 ,0);7,2483(0,9);7,2475(0,7);7,247(0,6);7,246(0,6);7,245(0,5);7,210(3, 2);7,170(3,2);7,033(6,9);6,996(2,2);6,896(3,5);5,408(10,1 );5,381 (1 ,6);4,171 (1 ,9);4,149( 1 ,3);3,867(0,6);3,762(16,0);3,540(1 ,0);3,518(2,1 );3,503(1 ,6);3,491 (2,0);3,477(1 ,1 );2,95 6(1 ,6);2,885(1 ,5);2,883(1 ,3);2,326(2,0);2,312(1 ,9);2,306(1 ,8);2,296(1 ,1 );2,214(0,8);2,1 97(1 ,6);2,177(2,4);2,170(1 ,7);2,162(1 ,3);2,134(0,6);2,090(4,3);2,044(0,8);1 ,549(9,3);1 , 259(0,9);0,921 (0,7);0,01 1 (0,5);0,010(0,7);0,008(5,2);0,007(1 ,3);0,006(1 ,4);0,005(1 ,7);0 ,004(2,2);0,000(175,5);-0,006(2,2);-0,007(2,0);-0,009(5,0);-0,050(1 ,4) Beispiel No. B1 -1 : 1H-NMR (400 MHz, CDCIs δ, ppm) (5.4), 7.2555 (4.1), 7.255 (3.6), 7.254 (3.0), 7.253 (2.5), 7.2523 (1, 7), 7.2515 (1 , 5), 7,251 (1,4), 7,250 (1,2), 7.249 (1, 0), 7.2483 (0.9), 7.2475 (0.7), 7.247 (0.6 7,246 (0.6), 7.245 (0.5), 7.210 (3, 2), 7.170 (3.2), 7.033 (6.9), 6.996 (2.2), 6.896 (3.5) 5,408 (10,1), 5,381 (1,6), 4,171 (1,9), 4,149 (1,3), 3,867 (0,6), 3,762 (16,0), 3,540 (1, 0); 3.518 (2.1), 3.503 (1, 6), 3.491 (2.0), 3.477 (1, 1), 2.95 6 (1, 6), 2.855 (1.5), 2.883 (1, 3 2,326 (2,0), 2,312 (1,9), 2,306 (1,8), 2,296 (1,1), 2,214 (0,8), 2,197 (1,6), 2,177 (2 2,170 (1, 7), 2,162 (1,3), 2,134 (0,6), 2,090 (4,3), 2,044 (0,8), 1, 549 (9,3), 1, 259 (0.9), 0.921 (0.7), 0.01 1 (0.5), 0.010 (0.7), 0.008 (5.2), 0.007 (1.3), 0.006 (1.4 0.005 (1, 7), 0, 004 (2.2), 0.000 (175.5), - 0.006 (2.2), - 0.007 (2.0), - 0.009 (5.0), - 0.050 (1, 4) Example No. B1 -1: 1 H-NMR (400 MHz, CDCl3 δ, ppm)
7,768(0,7);7,763(0,7);7,749(0,8);7,744(0,8);7,582(0,9);7,579(1 ,0);7,573(1 ,0);7,570(0,9) ;7,472(0,6);7,469(0,7);7,453(0,9);7,449(1 ,0);7,375(0,9);7,371 (0,8);7,356(0,6);7,351 (0,5 );7,333(0,7);7,329(0,7);7,314(0,9);7,310(0,9);7,264(9,1 );7,259(1 ,2);7,249(1 ,2);7,246(1 , 2);7,019(1 ,3);7,010(1 ,3);7,006(1 ,2);6,997(1 ,1 );5,297(2,6);5,174(4,4);3,449(16,0);2,043( 1 ,3);1 ,432(0,6);1 ,258(1 ,3);1 ,217(1 ,1 );0,000(2,9)  7.768 (0.7); 7.763 (0.7); 7.749 (0.8); 7.744 (0.8); 7.582 (0.9); 7.579 (1.0); 7.573 (1.0); 7.570 7.459 (0.9); 7.499 (0.9); 7.449 (1, 0); 7.375 (0.9); 7.371 (0.8); 7.356 (0.9); 0.6), 7.351 (0.5), 7.333 (0.7), 7.329 (0.7), 7.314 (0.9), 7.310 (0.9), 7.264 (9.1), 7.259 (1 , 2), 7.249 (1, 2), 7.246 (1,2), 7,019 (1,3), 7,010 (1,3), 7,006 (1,2), 6,997 (1,1), 5,297 (2, 6); 5.174 (4.4); 3.499 (16.0); 2.043 (1, 3); 1, 432 (0.6); 1, 258 (1, 3); 1, 217 (1, 1) ; 0,000 (2.9)
Beispiel No. B1 -61 : 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. B1 -61: 1 H-NMR (400 MHz, CDCIs δ, ppm)
7,922(1 ,3);7,903(1 ,5);7,759(1 ,3);7,757(1 ,4);7,740(1 ,6);7,737(1 ,7);7,666(0,9);7,662(0,9) ;7,647(1 ,9);7,643(1 ,7);7,627(1 ,2);7,623(1 ,1 );7,591 (0,9);7,586(0,9);7,574(1 ,5);7,571 (1 ,5 );7,555(2,0);7,551 (2,0);7,535(0,8);7,532(0,8);7,275(1 ,3);7,272(1 ,4);7,264(28,9);7,025(2 ,4);7,016(2,4);7,013(2,3);7,004(2,1 );5,299(6,8);5,215(4,3);4,130(0,7);4,1 12(0,7);3,514( 16,0);2,044(3,5);1 ,276(1 ,0);1 ,259(2,0);1 ,241 (0,9);0,000(9,9) 7,922 (1, 3); 7,903 (1,5); 7,759 (1,3); 7,757 (1,4); 7,740 (1,6); 7,737 (1,7); 7,666 (0,9); 7,662 (0.9); 7.647 (1, 9); 7.643 (1, 7); 7.627 (1, 2); 7.623 (1, 1); 7.591 (0.9); 7.586 (0.9); 7.574 ( 1, 5), 7.571 (1.5), 7.555 (2.0), 7.551 (2.0), 7.535 (0.8), 7.532 (0.8), 7.275 (1.3), 7.272 (1 7,216 (2,4); 7,013 (2, 3); 7,004 (2,1); 5,299 (6,8); 5,215 (4, 4); 7,264 (28,9); 7,025 (2,4); 4,130 (0.7); 4.1 12 (0.7); 3.514 (16.0); 2.044 (3.5); 1, 276 (1, 0); 1, 259 (2.0 ), 1, 241 (0.9), 0.000 (9.9)
Beispiel No. B1 -122: 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. -122 B1: 1 H-NMR (400 MHz, CDCIs δ, ppm)
8,355(1 ,1 );8,334(1 ,2);8,103(0,9);8,081 (1 ,0);7,965(1 ,2);7,962(1 ,3);7,955(1 ,3);7,952(1 ,3) ;7,932(0,8);7,91 1 (1 ,0);7,856(0,6);7,853(0,6);7,839(0,8);7,835(1 ,1 );7,831 (0,6);7,818(0,7 );7,814(0,6);7,803(1 ,6);7,782(1 ,5);7,709(0,8);7,706(0,8);7,691 (0,8);7,688(1 ,4);7,685(0, 9);7,671 (0,6);7,668(0,5);7,651 (1 ,4);7,648(1 ,4);7,638(1 ,5);7,636(1 ,4);7,606(0,9);7,603(0 ,9);7,593(0,9);7,591 (0,9);7,519(1 ,6);7,294(2,0);7,260(304,4);7,228(1 ,1 );7,162(1 ,5);7,15 2(1 ,5);7,150(1 ,6);7,140(1 ,4);7,136(0,7);7,126(0,6);7,123(0,7);7,1 13(0,6);6,996(1 ,7);5,6 10(4,3);3,981 (16,0);3,314(1 ,9);0,034(0,7);0,008(3,1 );0,000(105,9);-0,009(3,2) Beispiel No. B2-1 : 1H-NMR (400 MHz, CDCIs δ, ppm) 8.355 (1, 1), 8.344 (1,2), 8,103 (0,9), 8,081 (1, 0), 7,965 (1,2), 7,962 (1,3), 7,955 (1,3), 7,952 (1, 3); 7.932 (0.8); 7.91 1 (1, 0); 7.856 (0.6); 7.853 (0.6); 7.839 (0.8); 7.835 (1, 1) 7.831 (0.6), 7.818 (0.7), 7.814 (0.6), 7.803 (1, 6), 7.782 (1.5), 7.709 (0.8), 7.706 (0.8); 7.691 (0.8), 7.688 (1, 4), 7.685 (0.9), 7.671 (0.6), 7.668 (0.5), 7.651 (1.4), 7.648 (1, 4), 7.638 (1, 5); 7.636 (1, 4); 7.606 (0.9); 7.603 (0.9); 7.593 (0.9); 7.591 (0.9); 7.519 (1, 6); 7.294 ( 7,260 (304,4); 7,228 (1, 1); 7,162 (1, 5); 7,15 2 (1, 5); 7,150 (1, 6); 7,140 (1, 4); 7.136 (0.7), 7.126 (0.6), 7.123 (0.7), 7.1 13 (0.6), 6.996 (1, 7), 5.6-10 (4.3), 3.981 ( 16.0), 3.314 (1, 9), 0.034 (0.7), 0.008 (3.1), 0.000 (105.9), - 0.009 (3.2). B2-1: 1 H-NMR (400 MHz, CDCIs δ, ppm)
7,810(0,9);7,807(0,9);7,802(0,9);7,799(0,9);7,699(0,7);7,694(0,7);7,680(0,8);7,675(0,8) ;7,477(0,6);7,474(0,7);7,466(1 ,2);7,464(1 ,2);7,457(1 ,0);7,454(2,3);7,451 (1 ,4);7,374(0,8 );7,370(0,8);7,354(0,6);7,350(0,5);7,322(0,6);7,319(0,7);7,303(0,9);7,300(0,9);7,264(9, 1 );7,226(1 ,2);7,218(1 ,3);7,213(1 ,2);7,206(1 ,1 );5,298(1 ,5);5,236(4,4);3,434(16,0);0,000( 3,2)  7.810 (0.9); 7,807 (0.9); 7,802 (0.9); 7,799 (0.9); 7,699 (0.7); 7,694 (0.7); 7,680 (0.8); 7,675 (0.8); 7.477 (0.6); 7.474 (0.7); 7.466 (1, 2); 7.444 (1, 2); 7.457 (1, 0); 7.454 (2.3); 7.451 ( 1, 4), 7.374 (0.8), 7.370 (0.8), 7.354 (0.6), 7.350 (0.5), 7.322 (0.6), 7.319 (0.7), 7.303 (0 , 7,300 (0,9); 7,264 (9,1); 7,226 (1,2); 7,218 (1,3); 7,213 (1,2); 7,206 (1,1); 5,298 (1); 5), 5.236 (4.4), 3.434 (16.0), 0.000 (3.2)
Beispiel No. B2-21 : 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. B2-21: 1 H-NMR (400 MHz, CDCIs δ, ppm)
8,646(1 ,6);8,644(1 ,8);8,642(1 ,8);8,639(1 ,7);8,634(1 ,7);8,632(1 ,8);8,630(1 ,8);8,627(1 ,6) ;7,830(1 ,1 );7,754(0,9);7,749(0,9);7,735(2,2);7,730(2,2);7,716(1 ,9);7,71 1 (1 ,8);7,683(2,1 );7,664(1 ,1 );7,441 (2,4);7,438(2,4);7,429(2,7);7,426(2,6);7,363(1 ,5);7,360(1 ,5);7,351 (1 , 5);7,348(1 ,6);7,345(1 ,5);7,341 (1 ,4);7,332(1 ,3);7,329(1 ,3);7,265(39,1 );7,222(2,9);7,215( 2,9);7,210(2,6);7,202(2,5);5,299(7,6);5,181 (5,5);3,531 (16,0);1 ,286(0,7);0,000(13,7) 8,646 (1,6), 8,644 (1,8), 8,642 (1,8), 8,639 (1,7), 8,634 (1, 7), 8,632 (1,8), 8,630 (1,8), 8,627 (1, 6) 7.730 (1, 1), 7.754 (0.9), 7.749 (0.9), 7.735 (2.2), 7.730 (2.2), 7.716 (1.9), 7.71 1 (1, 7) 7,641 (2,1); 7,664 (1, 1); 7,441 (2,4); 7,438 (2,4); 7,429 (2,7); 7,426 (2,6); 7,363 (1, 5) 7,360 (1, 5); 7,351 (1, 5); 7,348 (1, 6); 7,345 (1, 5); 7,341 (1, 4); 7,332 (1, 3); 7,329 (1, 3) 7.265 (39.1), 7.222 (2.9), 7.215 (2.9), 7.210 (2.6), 7.202 (2.5), 5.299 (7.6), 5.181 (5.5); 3.531 (16.0); 1, 286 (0.7); 0.000 (13.7)
Beispiel No. B2-61 : 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. B2-61: 1 H-NMR (400 MHz, CDCIs δ, ppm)
7,829(0,7);7,827(0,7);7,809(0,8);7,807(0,9);7,796(0,8);7,793(0,9);7,788(0,9);7,785(0,8) ;7,759(0,7);7,757(0,7);7,740(0,8);7,737(0,8);7,627(1 ,0);7,623(0,9);7,607(0,7);7,604(0,6 );7,566(0,8);7,563(0,8);7,547(1 ,1 );7,544(1 ,1 );7,437(1 ,3);7,434(1 ,3);7,424(1 ,4);7,421 (1 , 4);7,263(14,4);7,226(1 ,5);7,219(1 ,4);7,214(1 ,3);7,206(1 ,3);5,299(3,5);5,281 (3,9);3,482( 16,0);0,000(5,2)  7,829 (0.7); 7.827 (0.7); 7,809 (0.8); 7,807 (0.9); 7,796 (0.8); 7,793 (0.9); 7,788 (0.9); 7,785 (0.8); 7,759 (0.7); 7,757 (0.7); 7,740 (0.8); 7,737 (0.8); 7,627 (1, 0); 7,623 (0.9); 7,607 ( 0.7), 7.604 (0.6), 7.566 (0.8), 7.563 (0.8), 7.547 (1, 1), 7.544 (1, 1), 7.437 (1, 3), 7.434 (1 7,424 (1,4); 7,421 (1,4); 7,263 (14,4); 7,226 (1,5); 7,219 (1,4); 7,214 (1,3); 7,206 (1); 3); 5,299 (3.5); 5.281 (3.9); 3.482 (16.0); 0.000 (5.2)
Beispiel No. B2-122: 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. B2-122: 1 H-NMR (400 MHz, CDCl3 δ, ppm)
8,188(2,8);8,167(3,0);8,101 (2,2);8,099(2,2);8,080(2,5);8,077(2,5);7,864(1 ,9);7,860(2,0) ;7,840(2,4);7,784(2,5);7,780(2,4);7,766(2,4);7,762(3,4);7,758(4,7);7,745(2,0);7,741 (1 ,9 );7,736(3,6);7,625(1 ,9);7,622(2,0);7,608(1 ,7);7,605(3,1 );7,602(1 ,8);7,587(1 ,4);7,585(1 , 4);7,520(1 ,1 );7,438(2,0);7,436(2,0);7,426(2,2);7,423(2,1 );7,274(0,5);7,273(0,6);7,271 (0 ,9);7,270(0,9);7,269(1 ,3);7,268(1 ,4);7,261 (193,0);7,214(3,2);7,207(3,2);7,202(2,9);7,19 4(2,8);6,997(1 ,1 );5,304(5,8);5,299(5,2);3,563(16,0);1 ,589(1 ,9);1 ,371 (2,0);1 ,333(0,6);1 , 286(3,1 );1 ,256(1 ,6);0,008(2,1 );0,007(0,7);0,006(0,8);0,005(0,9);0,004(1 ,2);0,000(68,0); -0,007(0,7);-0,009(2,0)  8,188 (2.8); 8,167 (3.0); 8,101 (2,2); 8,099 (2,2); 8,080 (2.5); 8,077 (2.5); 7,864 (1,9); 7,860 (2.0); 7.840 (2.4); 7.784 (2.5); 7.780 (2.4); 7.766 (2.4); 7.762 (3.4); 7.758 (4.7); 7.745 ( 7.741 (1.9), 7.736 (3.6), 7.625 (1.9), 7.622 (2.0), 7.608 (1, 7), 7.605 (3.1), 7.602 (1 , 8), 7,587 (1,4), 7,585 (1,4), 7,520 (1,1), 7,438 (2,0), 7,436 (2,0), 7,426 (2,2), 7,423 (2, 7,274 (0.5), 7.273 (0.6), 7.271 (0.9), 7.270 (0.9), 7.269 (1.3), 7.268 (1.4), 7.261 (193.0 7,214 (3,2), 7,207 (3,2), 7,202 (2,9), 7,19 4 (2,8), 6,997 (1, 1), 5,304 (5,8), 5,299 (5 , 2); 3.563 (16.0); 1, 589 (1, 9); 1, 371 (2.0); 1, 333 (0.6); 1, 286 (3.1); 1, 256 (1, 6); 0.008 (2.1); 0.007 (0.7); 0.006 (0.8); 0.005 (0.9); 0.004 (1, 2); 0.000 (68.0); -0.007 (0.7) - 0.009 (2.0)
Beispiel No. C1 -1 : 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. C1 -1: 1 H NMR (400 MHz, CDCls δ, ppm)
7,656(0,7);7,651 (0,7);7,637(0,8);7,632(0,8);7,476(0,6);7,472(0,7);7,456(0,9);7,452(1 ,0) ;7,409(1 ,3);7,407(1 ,4);7,405(1 ,4);7,402(1 ,4);7,388(0,5);7,374(0,9);7,370(0,8);7,355(0,6 );7,350(0,5);7,327(0,7);7,323(0,7);7,308(0,9);7,304(0,9);7,267(10,2);6,941 (1 ,2);6,939(1 ,2);6,933(1 ,2);6,931 (1 ,2);6,420(1 ,3);6,416(1 ,3);6,412(1 ,3);6,407(1 ,3);5,317(4,4);5,299( 3,1 );3,447(16,0);2,044(0,8);1 ,259(1 ,2);1 ,219(0,6);0,071 (2,2);0,000(3,5) Beispiel No. C1 -21 : 1H-NMR (400 MHz, CDCIs δ, ppm) 7.656 (0.7), 7.651 (0.7), 7.637 (0.8), 7.632 (0.8), 7.466 (0.6), 7.472 (0.7), 7.456 (0.9), 7.452 (1, 0); 7,409 (1,3); 7,407 (1,4); 7,405 (1,4); 7,402 (1,4); 7,388 (0,5); 7,374 (0,9); 7,370 ( 7.355 (0.6), 7.355 (0.5), 7.327 (0.7), 7.323 (0.7), 7.308 (0.9), 7.304 (0.9), 7.267 (10 , 2), 6,941 (1,2), 6,939 (1,2), 6,933 (1,2), 6,931 (1,2), 6,420 (1,3), 6,416 (1,3), 6,412 (1, 2), 3); 6,407 (1,3); 5,317 (4,4); 5,299 (3,1); 3,447 (16,0); 2,044 (0.8); 1, 259 (1, 2); 1, 219 (0.6); 0.071 (2.2); 0.000 (3.5) Example no. C1 -21: 1 H-NMR (400 MHz, CDCIs δ, ppm)
8,714(0,6);8,712(0,7);8,709(0,7);8,707(0,6);8,699(0,7);8,697(0,7);7,889(1 ,0);7,884(1 ,0) ;7,869(0,6);7,865(0,6);7,769(1 ,1 );7,750(0,8);7,605(1 ,5);7,603(1 ,6);7,601 (1 ,6);7,599(1 ,5 );7,520(0,6);7,506(0,6);7,503(0,6);7,494(0,6);7,491 (0,6);7,486(0,6);7,484(0,5);7,474(0, 5);7,373(1 ,4);7,371 (1 ,4);7,364(1 ,4);7,362(1 ,4);7,272(0,6);7,271 (0,6);7,2704(0,7);7,269 7(0,8);7,268(1 ,0);7,267(1 ,2);7,261 (91 ,5);6,565(1 ,4);6,561 (1 ,4);6,556(1 ,4);6,552(1 ,3);5, 401 (4,2);3,905(16,0);3,102(1 ,1 );0,008(1 ,0);0,000(32,0);-0,009(0,9) Beispiel No. C1 -61 : 1H-NMR (400 MHz, CDCIs δ, ppm) 8.714 (0.6), 8.712 (0.7), 8.709 (0.7), 8.707 (0.6), 8.699 (0.7), 8.697 (0.7), 7.889 (1.0), 7.884 (1, 0), 7.689 (0.6), 7.865 (0.6), 7.769 (1, 1), 7.750 (0.8), 7.605 (1.5), 7.603 (1, 6), 7.601 ( 1, 6), 7.599 (1.5), 7.520 (0.6), 7.506 (0.6), 7.503 (0.6), 7.494 (0.6), 7.491 (0.6), 7.486 (0 , 6); 7,484 (0.5); 7,474 (0, 5,7,373 (1,4), 7,371 (1,4), 7,364 (1,4), 7,362 (1,4), 7,272 (0,6), 7,271 (0,6), 7,2704 (0 7,269,7 (0,8); 7,268 (1, 0); 7,267 (1,2), 7,261 (91,5), 6,565 (1,4), 6,561 (1,4), 6,556 (1 , 4); 6,552 (1,3); 5,401 (4,2); 3,905 (16,0); 3,102 (1,1); 0,008 (1, 0); 0,000 (32,0); - 0,009 (0.9) Example No. C1 -61: 1 H-NMR (400 MHz, CDCIs δ, ppm)
7,809(0,7);7,807(0,8);7,790(0,9);7,788(0,9);7,752(0,8);7,749(0,8);7,732(0,9);7,730(1 ,0) ;7,648(0,5);7,645(0,6);7,629(1 ,1 );7,625(1 ,0);7,610(0,7);7,606(0,6);7,562(0,8);7,558(0,9 );7,543(1 ,2);7,539(1 ,2);7,523(0,6);7,404(1 ,5);7,401 (1 ,6);7,399(1 ,7);7,397(1 ,5);7,264(22 ,5);6,944(0,9);6,942(0,9);6,935(0,9);6,934(0,9);6,424(1 ,7);6,419(1 ,7);6,415(1 ,6);6,41 1 ( 1 ,6);5,369(4,0);5,300(2,4);3,501 (16,0);2,044(2,1 );1 ,277(0,6);1 ,259(1 ,2);1 ,241 (0,6);0,00 0(7,8)  7,809 (0.7); 7,807 (0.8); 7,790 (0.9); 7,788 (0.9); 7,752 (0.8); 7,749 (0.8); 7,732 (0.9); 7,730 (1, 0); 7.648 (0.5); 7.645 (0.6); 7.629 (1, 1); 7.625 (1, 0); 7.610 (0.7); 7.606 (0.6); 7.562 (0.6) 7.5), 7.558 (0.9), 7.543 (1.2), 7.539 (1.2), 7.523 (0.6), 7.404 (1.5), 7.401 (1, 6), 7.399 (1 7.397 (1, 5), 7.264 (22, 5), 6.944 (0.9), 6.942 (0.9), 6.935 (0.9), 6.934 (0.9), 6.424 (1, 6,419 (1, 6), 6,415 (1,6), 6,41 1 (1,6), 5,369 (4,0), 5,300 (2,4), 3,501 (16,0), 2,044 ( 2.1); 1, 277 (0.6); 1, 259 (1, 2); 1, 241 (0.6); 0.00 0 (7.8)
Beispiel No. C2-1 : 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. C2-1: 1 H-NMR (400 MHz, CDCIs δ, ppm)
7,831 (1 ,0);7,829(1 ,1 );7,827(1 ,1 );7,825(1 ,0);7,680(0,7);7,676(0,7);7,661 (0,9);7,657(0,8) ;7,477(0,7);7,473(0,7);7,457(1 ,0);7,454(1 ,1 );7,396(0,5);7,392(0,6);7,378(0,9);7,373(0,9 );7,357(1 ,6);7,352(2,6);7,348(1 ,4);7,328(0,7);7,324(0,7);7,309(0,9);7,305(0,9);7,267(7, 8);6,676(1 ,3);6,674(1 ,4);6,671 (1 ,4);6,670(1 ,3);5,299(3,8);5,226(4,5);3,417(16,0);0,000( 2,9) Beispiel No. C2-21 : 1H-NMR (400 MHz, CDCIs δ, ppm) 7.831 (1, 0), 7.829 (1, 1), 7.827 (1, 1), 7.825 (1.0), 7.680 (0.7), 7.676 (0.7), 7.661 (0.9), 7.657 (0.8); 7.477 (0.7); 7.473 (0.7); 7.457 (1, 0); 7.454 (1, 1); 7.396 (0.5); 7.392 (0.6); 7.378 ( 7.357 (0.9), 7.373 (0.9), 7.357 (1, 6), 7.352 (2.6), 7.348 (1, 4), 7.328 (0.7), 7.324 (0.7), 7.309 (0 , 9), 7.305 (0.9), 7.267 (7, 8), 6.676 (1, 3), 6.674 (1, 4), 6.671 (1, 4), 6.670 (1, 3), 5.299 (3, 8), 5.266 (4.5), 3.417 (16.0), 0.000 (2.9) Example no. C2-21: 1 H-NMR (400 MHz, CDCIs δ, ppm)
8,662(2,3);8,659(2,7);8,658(2,7);8,656(2,4);8,650(2,3);8,647(3,1 );8,643(2,2);8,020(1 ,4) ;7,799(0,8);7,794(0,9);7,779(2,5);7,775(2,5);7,761 (3,2);7,757(4,2);7,735(0,9);7,524(0,6 );7,403(1 ,9);7,398(1 ,9);7,391 (2,2);7,384(5,5);7,380(7,8);7,375(4,5);7,369(2,2);7,364(0, 7);7,277(0,5);7,276(0,6);7,2753(0,6);7,2745(0,6);7,274(0,7);7,272(1 ,0);7,265(88,8);7,0 01 (0,5);6,748(3,3);5,300(16,0);3,660(12,3);2,778(0,6);1 ,450(0,6);1 ,441 (0,6);1 ,371 (2,2); 1 ,333(0,5);1 ,286(3,2);1 ,256(1 ,9);0,008(0,9);0,000(32,1 );-0,009(0,9)  8.662 (2.3), 8.659 (2.7), 8.658 (2.7), 8.656 (2.4), 8.650 (2.3), 8.647 (3.1), 8.643 (2.2), 8.020 (1, 4); 7,799 (0.8); 7,794 (0.9); 7,779 (2.5); 7,775 (2.5); 7,761 (3,2); 7,757 (4,2); 7,735 ( 7.998 (1, 9); 7.391 (2.2); 7.384 (5.5); 7.380 (7.8); 7.375 (4 .9); , 5); 7,369 (2,2); 7,364 (0, 7); 7,277 (0.5); 7,276 (0.6); 7,2753 (0.6); 7,2745 (0.6); 7.274 (0.7), 7.272 (1.0), 7.265 (88.8), 7.0 01 (0.5), 6.748 (3.3), 5.300 (16.0), 3.660 (12.3 2,778 (0.6); 1, 450 (0.6); 1, 441 (0.6); 1, 371 (2.2); 1, 333 (0.5); 1, 286 (3.2); 1, 256 (1, 9); 0.008 (0.9); 0.000 (32.1); - 0.009 (0.9)
Beispiel No. C2-61 : 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. C2-61: 1 H-NMR (400 MHz, CDCIs δ, ppm)
7,81 1 (1 ,8);7,809(1 ,6);7,807(1 ,3);7,805(1 ,2);7,794(0,9);7,792(0,9);7,760(0,7);7,757(0,7) ;7,740(0,8);7,737(0,8);7,637(1 ,0);7,633(0,9);7,617(0,6);7,613(0,5);7,572(0,7);7,569(0,8 );7,553(1 ,1 );7,550(1 ,0);7,354(1 ,4);7,349(2,3);7,345(1 ,4);7,266(9,6);6,649(1 ,4);6,647(1 , 5);6,644(1 ,4);6,642(1 ,3);5,300(4,2);5,263(4,0);3,464(16,0);0,000(3,4) Beispiel No. C3-1 : 1H-NMR (400 MHz, CDCIs δ, ppm) 7.81 (1, 8), 7.809 (1, 6), 7.807 (1, 3), 7.805 (1, 2), 7.794 (0.9), 7.792 (0.9), 7.760 (0.7 7.757 (0.7), 7.740 (0.8), 7.737 (0.8), 7.637 (1, 0), 7.633 (0.9), 7.617 (0.6), 7.613 (0.5) 7.552 (0.7); 7.569 (0.8); 7.553 (1, 1); 7.550 (1, 0); 7.354 (1, 4); 7.349 (2.3); 7.345 (1, 4); 7.266 (9.6); 6.649 (1, 4); 6.647 (1, 5); 6.644 (1, 4); 6.642 (1, 3); 5.300 (4.2); 5.263 (4.0); 3.344 (16.0) 0.000 (3.4) Example No. C3-1: 1 H-NMR (400 MHz, CDCIs δ, ppm)
7,678(0,7);7,674(0,7);7,659(0,8);7,655(0,8);7,473(0,6);7,469(0,7);7,453(0,9);7,450(0,9) ;7,386(0,5);7,372(0,8);7,367(0,8);7,352(0,6);7,347(0,5);7,320(0,6);7,317(0,7);7,301 (0,8 );7,298(0,8);7,263(10,0);7,179(1 ,4);7,174(1 ,5);6,591 (1 ,3);6,590(1 ,2);6,5862(1 ,3);6,585 5(1 ,2);5,297(1 ,0);5,238(4,2);3,404(16,0);2,530(9,0);0,000(4,2)  7,678 (0.7); 7,674 (0.7); 7.659 (0.8); 7.655 (0.8); 7,473 (0.6); 7.469 (0.7); 7,453 (0.9); 7,450 (0.9); 7.386 (0.5); 7.372 (0.8); 7.367 (0.8); 7.352 (0.6); 7.377 (0.5); 7.320 (0.6); 7.317 ( 0.7), 7.301 (0.8), 7.298 (0.8), 7.263 (10.0), 7.179 (1, 4), 7.174 (1, 5), 6.591 (1, 3), 6.590 (1 , 2); 6,5862 (1,3), 6,585 5 (1,2), 5,297 (1, 0), 5,238 (4,2), 3,404 (16,0), 2,530 (9,0), 0,000 (4.2)
Beispiel No. C3-4: 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. C3-4: 1 H-NMR (400 MHz, CDCIs δ, ppm)
7,610(1 ,0);7,606(1 ,1 );7,590(1 ,1 );7,586(1 ,2);7,560(1 ,2);7,556(1 ,1 );7,540(1 ,5);7,536(1 ,2) ;7,261 (21 ,8);7,243(2,1 );7,223(1 ,1 );7,178(1 ,9);7,173(2,0);6,574(1 ,3);6,569(1 ,3);5,31 1 (4, 9);5,298(1 ,0);3,41 1 (16,0);2,521 (1 1 ,7);0,000(8,9)  7.610 (1, 0), 7.606 (1, 1), 7.590 (1, 1), 7.586 (1, 2), 7.560 (1, 2), 7.556 (1, 1), 7.540 (1, 5), 7.536 (1,2), 7,261 (21, 8), 7,243 (2,1), 7,223 (1,1), 7,178 (1, 9), 7,173 (2,0), 6,574 (1,3), 6,569 (U.S. 1, 3); 5.31 1 (4, 9); 5.298 (1, 0); 3.41 1 (16.0); 2.521 (1 1, 7); 0.000 (8.9)
Beispiel No. C3-21 : 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. C3-21: 1 H-NMR (400 MHz, CDCIs δ, ppm)
8,640(0,6);8,637(0,6);8,635(0,7);8,633(0,6);8,627(0,6);8,625(0,7);8,623(0,6);8,621 (0,6) ;7,717(1 ,0);7,712(1 ,0);7,698(0,7);7,693(0,7);7,633(0,7);7,630(1 ,2);7,627(0,7);7,61 1 (0,8 );7,346(0,6);7,343(0,6);7,334(0,6);7,331 (0,6);7,327(0,6);7,324(0,6);7,315(0,6);7,312(0, 6);7,262(19,5);7,157(1 ,6);7,152(1 ,7);6,545(1 ,3);6,540(1 ,3);5,120(4,7);3,457(16,0);2,45 3(10,2);0,000(8,8)  8,640 (0.6); 8.637 (0.6); 8,635 (0.7); 8.633 (0.6); 8,627 (0.6); 8,625 (0.7); 8,623 (0.6); 8.621 (0.6); 7.717 (1, 0); 7.712 (1, 0); 7.688 (0.7); 7.693 (0.7); 7.633 (0.7); 7.630 (1, 2); 7.627 ( 0.7); 7.61 1 (0.8); 7.346 (0.6); 7.343 (0.6); 7.334 (0.6); 7.331 (0.6); 7.327 (0.6); 7.324 (0.6), 7.315 (0.6), 7.312 (0, 6), 7.262 (19.5), 7.157 (1, 6), 7.152 (1, 7), 6.545 (1, 3), 6.540 (1, 3); 5,120 (4,7); 3,457 (16,0); 2,45 3 (10,2); 0,000 (8,8)
Beispiel No. C3-61 : 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. C3-61: 1 H-NMR (400 MHz, CDCIs δ, ppm)
7,815(0,6);7,813(0,7);7,795(0,8);7,793(0,8);7,756(0,6);7,755(0,6);7,753(0,7);7,752(0,6) ;7,736(0,8);7,733(0,8);7,632(1 ,0);7,628(0,9);7,612(0,6);7,609(0,5);7,567(0,8);7,563(0,8 );7,547(1 ,1 );7,544(1 ,0);7,262(15,8);7,176(1 ,6);7,171 (1 ,6);6,5592(1 ,3);6,5586(1 ,4);6,55 5(1 ,3);6,554(1 ,3);5,298(2,4);5,291 (3,7);3,450(16,0);2,503(9,7);0,000(7,1 ) Beispiel No. C4-61 : 1H-NMR (400 MHz, CDCIs δ, ppm) 7.815 (0.6); 7,813 (0.7); 7,795 (0.8); 7,793 (0.8); 7,756 (0.6); 7,755 (0.6); 7,753 (0.7); 7,752 (0.6); 7.736 (0.8); 7.733 (0.8); 7.632 (1.0); 7.628 (0.9); 7.612 (0.6); 7.609 (0.5); 7.5), 7.563 (0.8), 7.547 (1, 1), 7.544 (1.0), 7.262 (15.8), 7.176 (1, 6), 7.171 (1, 6), 6.5592 (1, 3); 6.5586 (1, 4); 6.55 5 (1, 3); 6,554 (1, 3); 5,298 (2,4); 5,291 (3,7); 3,450 (16, 0); 2,503 (9,7); 0,000 (7,1) Example no. C4-61: 1 H-NMR (400 MHz, CDCIs δ, ppm)
7,752(1 ,1 );7,750(1 ,1 );7,732(1 ,4);7,730(1 ,4);7,717(1 ,0);7,714(1 ,2);7,698(1 ,3);7,695(1 ,4) ;7,602(0,8);7,598(0,8);7,583(1 ,6);7,579(1 ,5);7,563(1 ,0);7,560(0,9);7,518(1 ,2);7,515(1 ,2 );7,499(1 ,7);7,496(1 ,7);7,480(0,7);7,477(0,6);7,261 (32,7);7,173(2,6);7,169(2,7);6,579(2 ,1 );6,574(2,1 );5,402(4,7);5,298(4,3);4,201 (0,5);4,191 (0,6);4,179(0,8);4,168(0,6);4,157( 0,6);3,494(1 ,0);3,487(0,7);3,479(0,7);3,472(0,7);3,466(0,9);2,492(16,0);2,302(0,9);2,29 8(0,6);2,290(0,8);2,284(0,8);2,273(0,5);2,138(0,5);2,134(0,7);2,126(0,6);2,1 14(1 ,1 );2,1 06(0,7);2,099(0,6);0,000(13,6) Beispiel No. D6-1 : 1H-NMR (400 MHz, CDCIs δ, ppm) 7.752 (1, 1), 7.750 (1, 1), 7.732 (1, 4), 7.730 (1, 4), 7.717 (1, 0), 7.714 (1, 2), 7.698 (1, 3), 7.695 (1, 4); 7.602 (0.8); 7.598 (0.8); 7.583 (1, 6); 7.579 (1, 5); 7.563 (1, 0); 7.560 (0.9); 7.518 ( 1, 2), 7.459 (1, 2), 7.499 (1, 7), 7.496 (1, 7), 7.480 (0.7), 7.477 (0.6), 7.261 (32.7), 7.173 (2 7,169 (2,7); 6,579 (2, 1); 6,574 (2,1); 5,402 (4,7); 5,298 (4,3); 4,201 (0,5); 4,191 (0); 4,179 (0.8); 4.168 (0.6); 4.157 (0.6); 3.494 (1, 0); 3.487 (0.7); 3.479 (0.7); 3.472 (0.7 3.466 (0.9), 2.492 (16.0), 2.302 (0.9), 2.29 8 (0.6), 2.290 (0.8), 2.284 (0.8), 2.273 (0 , 5), 2.138 (0.5), 2.134 (0.7), 2.126 (0.6), 2.1.14 (1, 1), 2.1.06 (0.7), 2.099 (0.6 ); 0.000 (13.6) Example No. D6-1: 1 H-NMR (400 MHz, CDCIs δ, ppm)
7,705(0,7);7,700(0,7);7,686(0,8);7,681 (0,8);7,496(0,6);7,492(0,7);7,476(0,9);7,472(1 ,1 ) ;7,432(0,5);7,428(0,6);7,414(0,9);7,409(0,8);7,394(0,6);7,389(0,5);7,371 (0,7);7,367(0,7 );7,352(0,9);7,348(0,9);7,267(8,9);5,303(6,2);5,067(4,5);3,421 (16,0);2,047(0,6);0,000(3 ,8)  7.705 (0.7), 7.700 (0.7), 7.686 (0.8), 7.681 (0.8), 7.496 (0.6), 7.492 (0.7), 7.466 (0.9), 7.472 (1, 1), 7.432 (0.5), 7.428 (0.6), 7.414 (0.9), 7.409 (0.8), 7.394 (0.6), 7.389 (0.5), 7.371 ( 7.377 (0.7), 7.352 (0.9), 7.348 (0.9), 7.267 (8.9), 5.303 (6.2), 5.067 (4.5), 3.421 (16 , 0); 2,047 (0,6); 0,000 (3, 8)
Beispiel No. D6-3: 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. D6-3: 1 H-NMR (400 MHz, CDCIs δ, ppm)
7,417(21 , 0);7,266(12,1 );5,302(3,2);4,807(5,2);3,352(16,0);2,047(0,6);1 , 610(1 ,0);0,000( 5,3)  7.417 (21, 0); 7.266 (12.1); 5.302 (3.2); 4.807 (5.2); 3.352 (16.0); 2.047 (0.6); 1, 610 (1, 0) 0.000 (5.3)
Beispiel No. D6-4: 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. D6-4: 1 H-NMR (400 MHz, CDCIs δ, ppm)
7,645(0,9);7,641 (1 ,0);7,625(1 ,0);7,621 (1 ,1 );7,601 (1 ,2);7,597(1 ,1 );7,581 (1 ,4);7,577(1 ,1 ) ;7,320(1 ,3);7,300(1 ,8);7,280(1 ,0);7,266(14,1 );5,302(4,0);5,132(4,6);3,432(16,0);2,047( 0,6);0,000(5,7)  7.645 (0.9), 7.641 (1, 0), 7.625 (1, 0), 7.621 (1, 1), 7.601 (1, 2), 7.557 (1, 1), 7.581 (1, 4), 7.577 (1, 1); 7,320 (1,3); 7,300 (1, 8); 7,280 (1, 0); 7,266 (14.1); 5,302 (4,0); 5,132 (4,6); 3,432 ( 16.0), 2.047 (0.6), 0.000 (5.7)
Beispiel No. D6-1 1 : 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. D6-1 1: 1 H NMR (400 MHz, CDCIs δ, ppm)
7,595(0,5);7,590(0,6);7,576(1 ,1 );7,572(1 ,2);7,557(0,6);7,553(0,7);7,483(0,8);7,481 (0,6) ;7,478(0,5);7,476(0,5);7,469(0,6);7,467(0,5);7,465(0,6);7,462(0,8);7,266(20,5);7,255(0, 9);7,252(1 ,0);7,236(1 ,6);7,233(1 ,7);7,217(0,8);7,214(0,8);7,191 (0,8);7,188(0,7);7,170(0 ,7);7,166(1 ,1 );7,163(0,8);7,144(0,7);7,142(0,6);5,302(4,0);4,934(4,6);3,392(15,4);3,389 (16,0);1 ,608(3,2);0,000(8,5)  7.595 (0.5), 7.590 (0.6), 7.576 (1, 1), 7.572 (1.2), 7.557 (0.6), 7.553 (0.7), 7.483 (0.8), 7.481 (0.6), 7.478 (0.5), 7.466 (0.5), 7.469 (0.6), 7.467 (0.5), 7.465 (0.6), 7.462 (0.8), 7.266 ( 7.25 (0, 9), 7.252 (1, 0), 7.236 (1, 6), 7.233 (1, 7), 7.217 (0.8), 7.214 (0.8), 7.191 (0 7.18 (0.7), 7.170 (0, 7), 7.166 (1, 1), 7.163 (0.8), 7.144 (0.7), 7.142 (0.6), 5.302 (4, 0); 4,934 (4,6); 3,392 (15,4); 3,389 (16,0); 1, 608 (3,2); 0,000 (8,5)
Beispiel No. D6-15: 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. D6-15: 1 H-NMR (400 MHz, CDCIs δ, ppm)
7,625(0,6);7,609(0,6);7,604(1 ,1 );7,588(1 ,1 );7,583(0,6);7,567(0,6);7,270(12,1 );6,985(0, 5);6,983(0,8);6,979(0,6);6,977(0,9);6,947(0,7);6,940(0,5);6,925(0,8);6,921 (0,9);6,915(0 ,6);6,900(0,7);6,894(0,6);5,304(4,9);4,891 (4,3);4,889(4,3);4,131 (0,6);4,1 13(0,6);3,391 ( 15,7);3,388(16,0);2,047(3,0);1 ,655(1 ,4);1 ,278(0,9);1 ,260(1 ,9);1 ,243(0,9);0,000(5,0)  7.625 (0.6), 7.609 (0.6), 7.604 (1, 1), 7.588 (1, 1), 7.583 (0.6), 7.567 (0.6), 7.270 (12.1), 6.985 (0.5), 6.983 (0.8), 6.979 (0.6), 6.977 (0.9), 6.947 (0.7), 6.940 (0.5), 6.925 (0.8), 6.921 ( 6.915 (0.6), 6.900 (0.7), 6.894 (0.6), 5.304 (4.9), 4.891 (4.3), 4.889 (4.3), 4.113 (0 , 6); 4.1 13 (0.6); 3.391 (15.7); 3.388 (16.0); 2.047 (3.0); 1.655 (1, 4); 1, 278 (0, 9); 1, 260 (1, 9); 1, 243 (0.9); 0.000 (5.0)
Beispiel No. D6-21 : 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. D6-21: 1 H-NMR (400 MHz, CDCIs δ, ppm)
8,650(0,5);8,647(0,6);8,645(0,6);8,643(0,5);8,638(0,5);8,635(0,6);8,633(0,6);7,766(0,9) ;7,761 (0,9);7,746(0,6);7,742(0,6);7,645(0,6);7,643(1 ,0);7,640(0,6);7,623(0,7);7,383(0,5 );7,380(0,5);7,370(0,5);7,367(0,5);7,364(0,5);7,263(25,0);4,970(4,2);3,460(16,0);0,000( 10,3) Beispiel No. D6-36: 1H-NMR (400 MHz, CDCIs δ, ppm) 8,650 (0.5); 8.647 (0.6); 8,645 (0.6); 8,643 (0.5); 8,638 (0.5); 8,635 (0.6); 8.633 (0.6); 7,766 7.761 (0.9), 7.746 (0.6), 7.742 (0.6), 7.645 (0.6), 7.643 (1.0), 7.640 (0.6), 7.623 ( 7.383 (0.5), 7.379 (0.5), 7.379 (0.5), 7.367 (0.5), 7.364 (0.5), 7.263 (25.0), 4.970 (4 , 2); 3,460 (16,0); 0,000 (10,3) Example No. D6-36: 1 H-NMR (400 MHz, CDCIs δ, ppm)
8,840(0,8);8,838(0,9);8,835(0,9);8,833(0,8);8,084(0,9);8,083(0,9);8,079(0,9);8,078(0,9) ;7,263(17,1 );5,300(0,9);5,193(3,8);3,615(16,0);2,085(0,8);0,000(7,3)  8,840 (0.8); 8,838 (0.9); 8,835 (0.9); 8.833 (0.8); 8,084 (0.9); 8,083 (0.9); 8.079 (0.9); 8,078 (0.9); 7.263 (17.1), 5.300 (0.9), 5.193 (3.8), 3.615 (16.0), 2.085 (0.8), 0.000 (7.3)
Beispiel No. D6-61 : 1H-NMR (400 MHz, CDC δ, ppm) Example No. D6-61: 1 H-NMR (400 MHz, CDC δ, ppm)
7,855(0,6);7,853(0,6);7,835(0,8);7,833(0,8);7,789(0,6);7,786(0,7);7,785(0,6);7,770(0,8) ;7,767(0,8);7,699(1 ,0);7,696(0,9);7,680(0,6);7,676(0,5);7,621 (0,8);7,618(0,8);7,602(1 ,1 );7,599(1 ,1 );7,264(20,6);5,094(4,0);3,479(16,0);1 ,584(1 ,0);0,000(7,9)  7,855 (0.6); 7,853 (0.6); 7,835 (0.8); 7,833 (0.8); 7.789 (0.6); 7,786 (0.7); 7,785 (0.6); 7,770 7.767 (0.8), 7.699 (1, 0), 7.696 (0.9), 7.680 (0.6), 7.676 (0.5), 7.621 (0.8), 7.618 (0.8) 0.8); 7.602 (1, 1); 7.599 (1, 1); 7.264 (20.6); 5.094 (4.0); 3.479 (16.0); 1, 584 (1, 0); 0.000 (7,9)
Beispiel No. D6-94: 1H-NMR (400 MHz, CDC δ, ppm) Example No. D6-94: 1 H-NMR (400 MHz, CDC δ, ppm)
8,455(1 ,1 );8,449(1 ,1 );7,886(0,8);7,880(0,8);7,866(0,9);7,859(0,9);7,432(1 ,2);7,412(1 ,1 ) ;7,410(1 ,1 );7,262(36,2);5,300(0,5);4,809(4,1 );3,458(13,9);3,415(16,0);2,045(0,6);1 ,564 (1 ,3);1 ,259(0,6);0,000(15,5)  8.455 (1, 1), 8.449 (1, 1), 7.886 (0.8), 7.880 (0.8), 7.866 (0.9), 7.859 (0.9), 7.432 (1, 2), 7.412 (1, 1); 7.410 (1, 1); 7.262 (36.2); 5.300 (0.5); 4.809 (4.1); 3.458 (13.9); 3.415 (16.0); 2.045 ( 0.6); 1, 564 (1, 3); 1, 259 (0.6); 0.000 (15.5)
Beispiel No. E1 -2: 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. E1 -2: 1 H-NMR (400 MHz, CDCIs δ, ppm)
7,526(1 ,2);7,522(0,9);7,474(0,6);7,463(0,6);7,457(0,8);7,452(0,6);7,393(2,2);7,386(0,7) ;7,376(0,9);7,261 (60,0);7,210(0,6);4,808(4,5);3,409(16,0);1 ,546(1 ,0);0,008(0,8);0,000( 26,0);-0,009(1 ,1 )  7.526 (1.2), 7.522 (0.9), 7.474 (0.6), 7.463 (0.6), 7.457 (0.8), 7.452 (0.6), 7.393 (2.2), 7.386 (0.7); 7.376 (0.9); 7.261 (60.0); 7.210 (0.6); 4.808 (4.5); 3.409 (16.0); 1, 546 (1.0); 0.008 (0.8); 0.000 (26.0); - 0.009 (1, 1)
Beispiel No. G1 -1 : 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. G1 -1: 1 H NMR (400 MHz, CDCl3 δ, ppm)
7,759(0,7);7,755(0,7);7,740(0,8);7,736(0,8);7,486(0,6);7,483(0,7);7,466(0,9);7,463(1 ,0) ;7,418(0,6);7,404(0,9);7,399(0,8);7,384(0,6);7,380(0,6);7,366(0,7);7,362(0,7);7,347(0,9 );7,343(0,9);7,266(10,5);5,302(1 ,4);5,099(4,4);3,447(16,0);0,000(4,5)  7.759 (0.7); 7,755 (0.7); 7,740 (0.8); 7,736 (0.8); 7,486 (0.6); 7,483 (0.7); 7,466 (0.9); 7,463 (1, 0); 7.418 (0.6); 7.404 (0.9); 7.399 (0.8); 7.384 (0.6); 7.380 (0.6); 7.366 (0.7); 7.362 ( 7.374 (0.9), 7.347 (0.9), 7.343 (0.9), 7.266 (10.5), 5.302 (1, 4), 5.099 (4.4), 3.447 (16.0), 0.000 (4 , 5)
Beispiel No. G1 -2: 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. G1 -2: 1 H-NMR (400 MHz, CDCIs δ, ppm)
7,529(0,6);7,525(1 ,3);7,520(0,8);7,462(0,6);7,447(0,6);7,443(1 ,0);7,438(0,7);7,403(0,9) ;7,399(1 ,4);7,395(0,6);7,389(1 ,3);7,388(1 ,3);7,370(1 ,1 );7,369(1 ,1 );7,266(14,4);5,302(0, 9);4,829(4,3);4,694(0,9);3,397(16,0);0,000(5,9)  7.529 (0.6), 7.525 (1.3), 7.520 (0.8), 7.462 (0.6), 7.447 (0.6), 7.433 (1, 0), 7.438 (0.7), 7.403 (0.9); 7.399 (1, 4); 7.959 (0.6); 7.389 (1, 3); 7.388 (1, 3); 7.379 (1, 1); 7.369 (1, 1); 7.266 (7) 14.4), 5.302 (0.9), 4.829 (4.3), 4.694 (0.9), 3.397 (16.0), 0.000 (5.9)
Beispiel No. G1 -3: 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. G1 -3: 1 H-NMR (400 MHz, CDCIs δ, ppm)
7,456(1 ,0);7,441 (0,7);7,435(3,6);7,430(0,7);7,423(0,9);7,418(4,0);7,412(0,7);7,398(0,7) ;7,396(1 ,0);7,2683(0,5);7,2675(0,6);7,267(0,7);7,266(0,9);7,265(1 ,2);7,264(1 ,7);7,261 ( 64,1 );7,258(0,8);5,300(1 ,1 );4,848(4,2);4,687(0,7);3,377(16,0);1 ,254(0,8);0,008(0,7);0,0 02(0,9);0,000(27,2);-0,003(1 ,4);-0,0035(0,9);-0,0043(0,5);-0,009(0,9) 7.456 (1, 0), 7.441 (0.7), 7.435 (3.6), 7.430 (0.7), 7.423 (0.9), 7.418 (4.0), 7.412 (0.7), 7.398 (0.7); 7.396 (1, 0); 7.2683 (0.5); 7.2675 (0.6); 7.267 (0.7); 7.266 (0.9); 7.265 (1, 2 7,264 (1, 7); 7,261 ( 64.1), 7.258 (0.8), 5.300 (1, 1), 4.848 (4.2), 4.687 (0.7), 3.377 (16.0), 1.254 (0.8), 0.008 (0.7); 0.0.02 (0.9); 0.000 (27.2); - 0.003 (1, 4); - 0.0035 (0.9); - 0.0043 (0.5) ; -0.009 (0.9)
Beispiel No. G8-1 : 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. G8-1: 1 H-NMR (400 MHz, CDCIs δ, ppm)
8,430(2,3);8,425(2,3);7,724(0,6);7,720(0,6);7,705(0,8);7,700(0,7);7,589(2,8);7,585(2,7) ;7,494(0,6);7,491 (0,6);7,474(0,9);7,471 (0,9);7,421 (0,5);7,417(0,5);7,403(0,9);7,398(0,8 );7,383(0,6);7,378(0,5);7,350(0,6);7,346(0,7);7,331 (0,8);7,328(0,8);7,267(10,8);5,302(2 ,0);5,122(4,2);3,459(16,0);0,000(4,6) Beispiel No. G8-3: 1H-NMR (400 MHz, CDCIs δ, ppm) 8,430 (2.3); 8,425 (2.3); 7,724 (0.6); 7,720 (0.6); 7,705 (0.8); 7,700 (0.7); 7,589 (2.8); 7,585 (2.7); 7.494 (0.6); 7.491 (0.6); 7.474 (0.9); 7.471 (0.9); 7.421 (0.5); 7.417 (0.5); 7.403 (7. 7.998 (0.8); 7.378 (0.8); 7.378 (0.5); 7.350 (0.6); 7.346 (0.7); 7.331 (0.8); 7.328 (0 .9); , 8), 7.267 (10.8), 5.302 (2, 0), 5.122 (4.2), 3.459 (16.0), 0.000 (4.6) Example no. G8-3: 1 H-NMR (400 MHz, CDCIs δ, ppm)
8,423(2,1 );8,419(2,1 );7,570(2,5);7,566(2,5);7,446(0,7);7,431 (0,6);7,424(3,6);7,421 (0,9) ;7,415(1 ,0);7,412(3,9);7,405(0,6);7,391 (0,6);7,390(0,8);7,268(7,7);5,302(3,5);4,857(4,4 );3,387(16,0);0,000(3,1 ) Beispiel No. G8-4: 1H-NMR (400 MHz, CDCIs δ, ppm) 8.423 (2.1), 8.419 (2.1), 7.570 (2.5), 7.566 (2.5), 7.446 (0.7), 7.431 (0.6), 7.424 (3.6), 7.421 (0.9); 7.415 (1.0); 7.412 (3.9); 7.405 (0.6); 7.391 (0.6); 7.390 (0.8); 7.268 (7.7); 5.302 ( 3.5), 4.857 (4.4), 3.387 (16.0), 0.000 (3.1). G8-4: 1 H-NMR (400 MHz, CDCIs δ, ppm)
8,430(2,3);8,426(2,4);7,662(0,9);7,658(1 ,0);7,642(1 ,0);7,638(1 ,1 );7,589(1 ,2);7,585(3,1 ) ;7,581 (2,1 );7,569(1 ,3);7,565(1 ,1 );7,294(1 ,2);7,274(1 ,9);7,266(1 1 ,2);7,255(1 ,0);5,302(2, 1 );5,182(4,5);3,471 (16,0);0,000(4,7) Beispiel No. G8-1 1 : 1H-NMR (400 MHz, CDCIs δ, ppm) 8.430 (2.3), 8.426 (2.4), 7.662 (0.9), 7.658 (1, 0), 7.642 (1.0), 7.638 (1, 1), 7.589 (1, 2), 7.585 (3.1); 7.581 (2.1); 7.569 (1, 3); 7.565 (1, 1); 7.294 (1, 2); 7.274 (1, 9); 7.266 (1 1, 2); 7.255 (1, 0); 5.302 (2, 1); 5.182 (4.5); 3.471 (16.0); 0.000 (4.7) Example no. G8-1 1: 1 NMR (400 MHz, CDCIs δ, ppm)
8,421 (3,7);8,417(3,8);7,61 1 (0,6);7,607(0,6);7,592(1 ,1 );7,588(1 ,2);7,577(4,2);7,573(4,6) ;7,569(0,8);7,473(0,8);7,471 (0,6);7,468(0,5);7,459(0,5);7,457(0,5);7,455(0,6);7,452(0,8 );7,267(15,8);7,235(0,9);7,232(1 ,0);7,216(1 ,5);7,213(1 ,7);7,197(0,7);7,194(0,8);7,189(0 ,8);7,187(0,7);7,169(0,7);7,165(1 ,1 );7,162(0,7);7,143(0,7);7,141 (0,6);5,302(0,5);4,990( 4,5);4,989(4,5);3,429(15,8);3,427(16,0);0,000(6,6)  8.421 (3.7), 8.417 (3.8), 7.61 1 (0.6), 7.607 (0.6), 7.592 (1, 1), 7.588 (1.2), 7.577 (4.2 7.573 (4.6); 7.569 (0.8); 7.473 (0.8); 7.471 (0.6); 7.468 (0.5); 7.459 (0.5); 7.457 (0.5) 7.455 (0.6), 7.452 (0.8), 7.267 (15.8), 7.235 (0.9), 7.232 (1, 0), 7.216 (1, 5), 7.213 (1, 7); 7.197 (0.7), 7.194 (0.8), 7.189 (0, 8), 7.187 (0.7), 7.169 (0.7), 7.165 (1, 1), 7.162 (0.7), 7.143 (0.7); 7.141 (0.6); 5.302 (0.5); 4.990 (4.5); 4.989 (4.5); 3.499 (15.8); 3,427 (16.0); 0.000 ( 6,6)
Beispiel No. G8-15: 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. G8-15: 1 H-NMR (400 MHz, CDCIs δ, ppm)
8,420(3,7);8,416(3,8);7,622(0,6);7,617(1 ,1 );7,601 (1 ,1 );7,596(0,6);7,580(0,6);7,567(4,4) ;7,562(4,3);7,269(12,3);6,971 (0,5);6,957(0,7);6,951 (1 ,0);6,943(0,8);6,938(0,7);6,931 (0, 5);6,930(0,6);6,922(0,8);6,918(0,8);6,912(0,6);6,897(0,7);6,890(0,5);5,302(14,3);4,940( 4,2);4,938(4,2);3,427(15,8);3,425(16,0);2,046(0,7);0,000(4,4) Beispiel No. G8-21 : 1H-NMR (400 MHz, CDCIs δ, ppm) 8.420 (3.7), 8.416 (3.8), 7.622 (0.6), 7.617 (1, 1), 7.601 (1, 1), 7.596 (0.6), 7.580 (0.6), 7.567 (4.4); 7.562 (4.3); 7.269 (12.3); 6.971 (0.5); 6.957 (0.7); 6.951 (1.0); 6.943 (0.8); 6.938 ( 0.7), 6.931 (0.5), 6.930 (0.6), 6.922 (0.8), 6.918 (0.8), 6.912 (0.6), 6.897 (0.7), 6.890 (0 , 5); 5,302 (14.3); 4,940 (4,2); 4,938 (4,2); 3,427 (15,8); 3,425 (16,0); 2,046 (0,7); 0,000 (4, 4) Example No. G8-21: 1 H-NMR (400 MHz, CDCls δ, ppm)
8,648(0,5);8,646(0,6);8,644(0,5);8,639(0,5);8,636(0,6);8,634(0,6);8,407(2,0);8,402(2,0) ;7,741 (0,9);7,736(0,9);7,722(0,6);7,717(0,6);7,651 (0,6);7,648(1 ,0);7,645(0,7);7,629(0,7 );7,559(2,0);7,555(1 ,9);7,372(0,5);7,369(0,5);7,360(0,5);7,357(0,5);7,353(0,5);7,266(9, 6);5,300(0,8);5,023(4,4);3,495(16,0);0,000(4,0)  8.648 (0.5); 8,646 (0.6); 8,644 (0.5); 8,639 (0.5); 8,636 (0.6); 8,634 (0.6); 8,407 (2.0); 8,402 (2.0), 7.741 (0.9), 7.736 (0.9), 7.722 (0.6), 7.717 (0.6), 7.651 (0.6), 7.648 (1.0), 7.645 ( 0.7), 7.629 (0.7), 7.559 (2.0), 7.555 (1.9), 7.372 (0.5), 7.369 (0.5), 7.360 (0.5), 7.357 (0 , 5), 7.353 (0.5), 7.266 (9, 6), 5.300 (0.8), 5.023 (4.4), 3.495 (16.0), 0.000 (4.0)
Beispiel No. G8-36: 1H-NMR (400 MHz, CDC δ, ppm) Example No. G8-36: 1 H-NMR (400 MHz, CDC δ, ppm)
8,838(1 ,2);8,835(1 ,1 );8,403(2,0);8,399(1 ,9);8,091 (1 ,2);8,087(1 ,1 );7,565(1 ,4);7,561 (1 ,3) ;7,262(31 ,4);5,262(4,3);3,646(16,0);1 ,573(1 ,6);0,000(13,4);-0,009(0,6)  8,838 (1,2), 8,835 (1,1), 8,403 (2,0), 8,399 (1,9), 8,091 (1,2), 8,087 (1,1), 7,565 (1,4), 7,561 (1, 3); 7,262 (31, 4); 5,262 (4,3); 3,646 (16,0); 1, 573 (1, 6); 0,000 (13,4); - 0,009 (0,6)
Beispiel No. G8-61 : 1H-NMR (400 MHz, CDC δ, ppm) Example No. G8-61: 1 H-NMR (400 MHz, CDC δ, ppm)
8,431 (2,2);8,427(2,1 );7,866(0,7);7,848(0,8);7,784(0,6);7,781 (0,7);7,765(0,8);7,762(0,8) ;7,666(0,9);7,662(0,8);7,647(0,6);7,643(0,5);7,604(0,7);7,601 (0,7);7,589(2,0);7,585(2,9 );7,582(1 ,1 );7,263(42,1 );5,302(2,8);5,138(4,2);3,518(16,0);1 ,580(5,3);0,000(15,0)  8.431 (2.2); 8.427 (2.1); 7.866 (0.7); 7.848 (0.8); 7.784 (0.6); 7.781 (0.7); 7.765 (0.8); 7.762 (0.8); 7.666 (0.9); 7.662 (0.8); 7.647 (0.6); 7.643 (0.5); 7.604 (0.7); 7.601 (0.7); 2.0), 7.585 (2.9), 7.582 (1, 1), 7.263 (42.1), 5.302 (2.8), 5.138 (4.2), 3.518 (16.0), 1.580 0.000 (15.0) (5.3)
Beispiel No. G8-94: 1H-NMR (400 MHz, CDCb δ, ppm) Example No. G8-94: 1 H-NMR (400 MHz, CDCb δ, ppm)
8,447(1 ,2);8,442(1 ,2);8,425(2,5);8,421 (2,5);7,915(0,9);7,909(0,9);7,895(0,9);7,888(0,9) ;7,572(1 ,1 );7,568(1 ,1 );7,520(0,6);7,41 1 (1 ,4);7,410(1 ,3);7,390(1 ,2);7,389(1 ,2);7,2704(0, 6);7,2697(0,7);7,269(0,6);7,268(0,9);7,267(1 ,0);7,2664(1 ,3);7,2656(1 ,5);7,265(2,0);7,2 64(2,6);7,261 (1 13,6);7,258(2,0);7,257(1 ,1 );7,256(0,8);7,255(0,6);7,21 1 (1 ,0);6,997(0,6); 4,869(3,5);3,453(16,0);2,708(0,6);1 ,558(2,7);0,008(1 ,4);0,005(0,5);0,004(0,7);0,003(1 , 0);0,002(1 ,8);0,000(47,4);-0,003(2,4);-0,004(0,9);-0,005(0,7);-0,006(0,6);-0,008(1 ,4)  8.447 (1, 2), 8.442 (1.2), 8.425 (2.5), 8.421 (2.5), 7.915 (0.9), 7.909 (0.9), 7.895 (0.9), 7.888 (0.9); 7,572 (1, 1); 7,568 (1, 1); 7,520 (0,6); 7,41 1 (1, 4); 7,410 (1, 3); 7,390 (1, 2) 7.289 (0.7), 7.269 (0.6), 7.268 (0.9), 7.267 (1, 0), 7.2664 (1, 3); 7.2656 (1.5), 7.265 (2.0), 7.2 64 (2.6), 7.261 (1 13.6), 7.258 (2.0), 7.257 (1 , 1), 7.256 (0.8), 7.255 (0.6), 7.21 1 (1, 0), 6.997 (0.6); 4.689 (3.5); 3.453 (16.0); 2.708 (0.6); 1.558 (2.7); 0.008 (1, 4); 0.005 (0.5); 0.004 (0.7) 0.003 (1, 0), 0.002 (1, 8), 0.000 (47.4), - 0.003 (2.4), - 0.004 (0.9), - 0.005 (0.7), - 0.006 (0 , 6); - 0.008 (1, 4)
Beispiel No. G9-1 : 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. G9-1: 1 H-NMR (400 MHz, CDCIs δ, ppm)
8,430(7,2);8,426(7,1 );7,598(3,9);7,594(3,8);7,586(2,5);7,582(2,5);7,567(2,7);7,563(2,7) ;7,462(2,2);7,459(2,3);7,442(3,3);7,439(3,3);7,376(1 ,8);7,371 (1 ,8);7,357(2,9);7,353(2,6 );7,337(1 ,9);7,333(1 ,7);7,282(2,2);7,279(2,3);7,273(0,6);7,272(0,7);7,268(21 ,1 );7,266(1 ,1 );7,263(3,0);7,260(2,9);7,245(1 ,3);7,241 (1 ,3);5,321 (16,0);5,299(1 ,4);4,239(1 ,0);4,230 (1 ,1 );4,218(1 ,5);4,206(1 ,2);4,196(1 ,1 );3,463(0,7);3,457(0,8);3,448(0,8);3,441 (1 ,8);3,43 5(1 ,3);3,427(1 ,5);3,420(1 ,4);3,413(1 ,7);3,407(0,7);3,398(0,8);3,392(0,7);2,310(0,6);2,3 03(0,9);2,296(0,9);2,289(1 ,6);2,287(1 ,5);2,283(1 ,2);2,275(1 ,4);2,270(1 ,7);2,265(1 ,0);2, 258(1 ,0);2,248(0,6);2,080(0,6);2,067(1 ,0);2,062(1 ,4);2,055(1 ,2);2,045(2,2);2,042(2,1 );2 ,035(1 ,4);2,027(1 ,2);0,000(9,6) Beispiel No. G9-3: 1H-NMR (400 MHz, CDCIs δ, ppm) 8.430 (7.2); 8.426 (7.1); 7.598 (3.9); 7.594 (3.8); 7.586 (2.5); 7.582 (2.5); 7.567 (2.7); 7.563 (2.7); 7.462 (2.2); 7.459 (2.3); 7.442 (3.3); 7.439 (3.3); 7.376 (1.8); 7.371 (1, 8); 2.35), 7.353 (2.6), 7.373 (2.6), 7.337 (1, 9), 7.333 (1, 7), 7.282 (2.2), 7.279 (2.3), 7.273 (0.6), 7.272 (0 7,268 (21,1); 7,266 (1,1); 7,263 (3,0); 7,260 (2,9); 7,245 (1,3); 7,241 (1,3); 5,321 (16); 4,239 (1, 4), 4,239 (1, 0), 4,230 (1,1), 4,218 (1,5), 4,206 (1,2), 4,196 (1,1), 3,463 (0,7 3.457 (0.8), 3.448 (0.8), 3.441 (1.8), 3.43 5 (1, 3), 3.347 (1.5), 3.420 (1.4), 3.413 (1 , 7), 3.407 (0.7), 3.398 (0.8), 3.322 (0.7), 2.310 (0.6), 2.3 03 (0.9), 2.296 (0.9), 2.289 (1, 6); 2,287 (1,5), 2,283 (1,2), 2,275 (1,4), 2,270 (1,7), 2,265 (1,0), 2, 258 (1,0); 2.248 (0.6), 2.080 (0.6), 2.067 (1.0), 2.062 (1.4), 2.055 (1.2), 2.045 (2.2), 2.042 (2.1), 2 , 035 (1, 4), 2.027 (1, 2), 0.000 (9.6) Example No. G9-3: 1 H-NMR (400 MHz, CDCls δ, ppm)
8,422(5,5);8,418(5,5);7,576(4,0);7,573(3,8);7,343(44,8);7,293(0,5);7,262(56,2);5,053(1 6,0);4,165(1 ,2);4,156(1 ,4);4,144(1 ,9);4,131 (1 ,6);4,122(1 ,3);3,376(0,8);3,371 (0,9);3,355 (2,0);3,349(1 ,5);3,341 (1 ,8);3,333(1 ,5);3,327(1 ,9);3,312(0,9);3,306(0,8);2,317(0,7);2,31 0(1 ,1 );2,304(1 ,1 );2,297(1 ,8);2,283(1 ,7);2,277(2,1 );2,265(1 ,2);2,257(0,8);2,085(0,9);2,0 52(0,6);2,045(1 ,2);2,034(1 ,6);2,026(1 ,5);2,017(2,4);2,007(1 ,7);1 ,999(1 ,3);1 ,601 (2,9);1 , 255(2,8);1 ,241 (0,6);0,008(0,7);0,000(23,3);-0,009(0,9) Beispiel No. G9-4: 1H-NMR (400 MHz, CDCIs δ, ppm) 8,422 (5.5); 8,418 (5.5); 7,576 (4.0); 7.573 (3.8); 7,343 (44.8); 7,293 (0.5); 7,262 (56.2); 5,053 (1 6,0), 4,165 (1,2), 4,156 (1,4), 4,144 (1,9), 4,131 (1,6), 4,122 (1,3), 3,376 (0,8), 3,371 (0.9); 3.355 (2.0); 3.349 (1, 5); 3.341 (1, 8); 3.333 (1, 5); 3.327 (1, 9); 3,312 (0,9); 3,306 ( 0.8), 2.317 (0.7), 2.31 0 (1, 1), 2.304 (1, 1), 2.297 (1.8), 2.283 (1, 7), 2.277 (2.1); 2,265 (1,2), 2,257 (0.8), 2.085 (0.9), 2.0 52 (0.6), 2.045 (1.2), 2.034 (1.6), 2.026 (1.5) 2.017 (2.4); 2.007 (1, 7); 1, 999 (1, 3); 1, 601 (2.9); 1, 255 (2.8); 1, 241 (0.6 0.008 (0.7); 0.000 (23.3); 0.009 (0.9) Example no. G9-4: 1 H-NMR (400 MHz, CDCls δ, ppm)
8,430(7,5);8,426(7,6);7,592(5,5);7,587(5,4);7,545(2,9);7,541 (3,9);7,525(3,4);7,521 (6,9) ;7,516(2,7);7,501 (3,9);7,497(2,7);7,270(0,5);7,264(44,7);7,224(3,8);7,214(0,5);7,205(6, 4);7,185(3,1 );5,372(16,0);5,300(3,3);4,246(1 ,1 );4,237(1 ,1 );4,225(1 ,6);4,213(1 ,2);4,204( 1 ,1 );3,468(0,7);3,462(0,8);3,453(0,8);3,447(1 ,8);3,440(1 ,3);3,432(1 ,4);3,425(1 ,4);3,419 (1 ,7);3,403(0,8);3,397(0,7);2,323(0,6);2,316(0,9);2,309(0,9);2,300(1 ,6);2,297(1 ,2);2,28 8(1 ,4);2,284(1 ,7);2,271 (1 ,0);2,261 (0,6);2,104(0,6);2,091 (1 ,0);2,087(1 ,4);2,079(1 ,2);2,0 76(1 ,4);2,069(2,1 );2,066(2,1 );2,059(1 ,4);2,052(1 ,2);2,045(0,9);1 ,635(1 ,2);0,008(0,6);0, 000(19,4);-0,009(0,5) Beispiel No. G9-1 1 1H-NMR (400 MHz, CDCIs δ, ppm) 8.430 (7.5), 8.426 (7.6), 7.592 (5.5), 7.587 (5.4), 7.545 (2.9), 7.541 (3.9), 7.525 (3.4), 7.521 (6.9), 7.516 (2.7), 7.551 (3.9), 7.497 (2.7), 7.270 (0.5), 7.264 (44.7), 7.224 (3.8), 7.214 ( 0.5), 7.205 (6, 4), 7.185 (3.1), 5.372 (16.0), 5.300 (3.3), 4.246 (1, 1), 4.237 (1, 1), 4.225 (1 , 4,213 (1, 1); 4,468 (0,7); 3,462 (0,8); 3,453 (0,8); 3,447 (1, 8); 3,440 (1, 2); 3), 3,432 (1,4), 3,425 (1,4), 3,419 (1,7), 3,403 (0,8), 3,397 (0,7), 2,323 (0,6), 2,316 (0,9 2.309 (0.9), 2.309 (0.9), 2.300 (1, 6), 2.297 (1, 2), 2.28 8 (1, 4), 2.284 (1, 7), 2.271 (1, 0), 2.261 (0 , 6); 2.104 (0.6); 2.091 (1, 0); 2.087 (1, 4); 2.079 (1, 2); 2.076 (1, 4); 2.069 (2.1); 2.066 (2.1); 2.059 (1, 4); 2.052 (1, 2); 2.045 (0.9); 1, 635 (1, 2); 0.008 (0.6); 0.000 (19.4 ) - 0.009 (0.5) Example no. G9-1 1 1 H-NMR (400 MHz, CDCIs δ, ppm)
8,419(12,8);8,415(12,7);7,582(7,7);7,578(7,5);7,491 (1 ,9);7,486(2,4);7,471 (3,7);7,467(4 ,3);7,452(2,1 );7,448(2,3);7,433(1 ,3);7,428(1 ,2);7,419(1 ,5);7,414(2,6);7,410(1 ,7);7,407( 1 ,7);7,400(2,0);7,399(1 ,9);7,396(2,0);7,394(2,9);7,389(1 ,6);7,380(1 ,7);7,375(1 ,5);7,265 (62,7);7,215(0,5);7,151 (2,5);7,149(5,0);7,146(4,0);7,143(2,6);7,132(4,8);7,130(6,2);7,1 26(3,1 );7,121 (3,7);7,1 18(2,5);7,1 13(2,8);7,1 10(2,6);7,100(2,5);7,097(2,0);5,299(4,2);5, 192(16,0);5,190(15,9);4,203(1 ,9);4,195(2,1 );4,182(2,9);4,170(2,3);4,160(2,0);4,130(0,7 );4,1 12(0,6);3,445(1 ,2);3,440(1 ,3);3,424(2,9);3,418(2,2);3,410(2,7);3,403(2,2);3,397(2, 8);3,382(1 ,2);3,375(1 ,2);2,313(1 ,1 );2,306(1 ,6);2,299(1 ,7);2,292(2,8);2,286(2,3);2,278(2 ,6);2,273(3,1 );2,261 (1 ,8);2,253(1 ,2);2,085(1 ,1 );2,072(1 ,9);2,067(2,6);2,060(2,4);2,050( 3,8);2,047(3,9);2,045(5,0);2,040(2,7);2,032(2,1 );2,025(1 ,2);2,016(0,5);2,012(0,6);1 ,671 (2,1 );1 ,277(0,9);1 ,259(2,0);1 ,241 (0,9);0,008(0,8);0,000(26,2);-0,009(0,8) Beispiel No. G9-15: 1H-NMR (400 MHz, CDCIs δ, ppm) 8.419 (12.8), 8.415 (12.7), 7.582 (7.7), 7.578 (7.5), 7.491 (1, 9), 7.486 (2.4), 7.471 (3.7), 7.467 (4, 3); 7.452 (2.1); 7.448 (2.3); 7.433 (1, 3); 7.428 (1, 2); 7.419 (1, 5); 7.414 (2.6); 7.410 ( 7,707 (1, 7), 7,400 (2,0), 7,399 (1, 9), 7,396 (2,0), 7,394 (2,9), 7,389 (1, 6), 7,380 (1 7, 775 (1, 5), 7.265 (62.7), 7.215 (0.5), 7.151 (2.5), 7.149 (5.0), 7.146 (4.0), 7.143 (2, 7,132 (4,8), 7,130 (6,2), 7,1 26 (3,1), 7,121 (3,7), 7,1 18 (2,5), 7,1 13 (2 , 7,1,10 (2,6); 7,100 (2.5); 7,097 (2,0); 5,299 (4,2); 5,192 (16,0); 5,190 (15.9); 4.193 (1, 9), 4.195 (2.1), 4.182 (2.9), 4.170 (2.3), 4.160 (2.0), 4.130 (0.7), 4.1 12 (0, 6,445 (1,2), 3,440 (1,3), 3,424 (2,9), 3,418 (2,2), 3,410 (2,7), 3,403 (2,2), 3,397 (2, 8 3,382 (1,2), 3,375 (1,2), 2,313 (1,1), 2,306 (1,6), 2,299 (1, 7), 2,292 (2,8), 2,286 (2,3) 2,278 (2,6), 2,273 (3,1), 2,261 (1,8), 2,253 (1,2), 2,085 (1,1), 2,072 (1,9), 2,067 (2,6); 2.060 (2.4); 2.050 (3.8); 2.047 (3.9); 2.045 (5.0); 2.040 (2.7); 2.032 (2.1); 2.025 (1, 2); 2.016 (0.5); 2.012 (0.6); 1, 671 (2.1); 1, 277 (0.9); 1, 259 (2.0); 1, 241 (0.9); 0.008 (0.8); 0,000 (26.2) - 0.009 (0.8) Example No. G9-15: 1 H-NMR (400 MHz, CDCls δ, ppm)
8,419(12,4);8,415(12,4);7,572(16,0);7,568(15,1 );7,491 (1 ,5);7,475(1 ,7);7,470(2,7);7,45 4(2,9);7,448(1 ,5);7,437(0,5);7,432(1 ,2);7,2724(0,6);7,2716(0,7);7,265(62,0);6,902(1 ,3); 6,896(2,3);6,893(1 ,2);6,889(2,1 );6,887(2,0);6,882(1 ,6);6,875(3,7);6,869(5,6);6,862(1 ,4) ;6,854(1 ,7);6,849(4,5);6,842(1 ,0);5,300(8,2);5,149(12,8);5,146(12,6);4,187(1 ,5);4,182( 1 ,7);4,173(1 ,9);4,161 (2,6);4,148(2,1 );4,139(1 ,8);3,436(1 ,1 );3,432(1 ,1 );3,415(2,5);3,410 (1 ,8);3,401 (2,3);3,394(1 ,8);3,388(2,4);3,372(1 ,0);3,367(1 ,0);2,322(0,9);2,316(1 ,4);2,30 9(1 ,5);2,302(2,4);2,296(1 ,9);2,288(2,2);2,282(2,6);2,271 (1 ,6);2,263(1 ,0);2,109(0,9);2,0 96(1 ,6);2,091 (2,2);2,084(2,0);2,072(3,8);2,064(2,3);2,056(1 ,8);2,049(1 ,0);2,045(0,5);2, 036(0,5);1 ,671 (0,8);1 ,254(0,6);0,008(0,8);0,000(26,3);-0,009(0,8)  8.419 (12.4); 8.415 (12.4); 7.572 (16.0); 7.568 (15.1); 7.491 (1, 5); 7.475 (1, 7); 7.470 (2.7); 7 , 45 4 (2.9), 7.448 (1, 5), 7.437 (0.5), 7.432 (1.2), 7.2724 (0.6), 7.2716 (0.7), 7.265 ( 62.0), 6.902 (1, 3); 6.896 (2.3), 6.893 (1.2), 6.889 (2.1), 6.887 (2.0), 6.882 (1.6), 6.875 (3.7), 6.689 (5.6), 6.862 (1,4); 6,854 (1, 7); 6,849 (4,5); 6,842 (1,0); 5,300 (8,2); 5,149 (12,8); 5,146 (12,6); 4,187 ( 1, 5), 4,182 (1, 7), 4,173 (1, 9), 4,161 (2,6), 4,148 (2,1), 4,139 (1, 8), 3,436 (1,1), 3,432 (1 , 1), 3,415 (2,5), 3,410 (1, 8), 3,401 (2,3), 3,394 (1, 8), 3,388 (2,4), 3,372 (1, 0), 3,367 (1, 2,322 (1,4); 2,30,9 (1,5); 2,302 (2,4); 2,296 (1,9); 2,288 (2,2,2); 2,282 ( 2,6), 2,271 (1,6), 2,263 (1,0), 2,109 (0,9), 2,096 (1,6), 2,091 (2,2), 2,084 (2,0); 2.072 (3.8); 2.064 (2.3); 2.056 (1.8); 2.049 (1.0); 2.045 (0.5); 2.036 (0.5); 1.671 (0); 8), 1, 254 (0.6), 0.008 (0.8), 0.000 (26.3), - 0.009 (0.8)
Beispiel No. G9-21 : 1H-NMR (400 MHz, CDC δ, ppm) Example No. G9-21: 1 H-NMR (400 MHz, CDC δ, ppm)
8,609(1 ,8);8,607(2,0);8,605(2,0);8,602(1 ,8);8,597(1 ,8);8,595(2,0);8,593(2,0);8,590(1 ,8) ;8,397(7,5);8,393(7,4);7,674(1 ,4);7,670(1 ,5);7,655(3,2);7,651 (3,1 );7,636(2,1 );7,631 (2,0 );7,551 (9,2);7,547(8,9);7,510(2,1 );7,507(3,5);7,505(2,2);7,490(1 ,7);7,488(2,8);7,485(1 , 7);7,323(1 ,9);7,320(1 ,9);7,31 1 (1 ,9);7,308(1 ,9);7,304(1 ,8);7,301 (1 ,7);7,292(1 ,7);7,289(1 ,7);7,270(0,6);7,265(40,1 );5,299(0,7);5,180(16,0);4,162(0,7);4,159(0,8);4,155(0,9);4,15 2(0,9);4,148(1 ,0);4,145(1 ,2);4,137(1 ,2);4,131 (1 ,7);4,126(1 ,2);4,1 19(1 ,4);4,1 16(1 , 1 );4,1 1 1 (1 ,0);4,108(1 ,0);4,105(0,9);4,101 (0,8);3,742(0,8);3,736(0,9);3,728(0,8);3,722(1 ,9);3, 715(1 ,2);3,713(1 ,1 );3,707(1 ,7);3,701 (1 ,1 );3,699(1 ,1 );3,692(1 ,7);3,686(0,8);3,678(0,7);3 ,672(0,7);2,288(0,9);2,282(1 ,0);2,273(1 ,5);2,268(1 ,2);2,261 (1 ,5);2,258(1 ,2);2,254(1 ,6); 2,243(1 ,0);2,234(0,7);2,097(0,6);2,093(1 ,0);2,090(1 ,2);2,087(1 ,2);2,084(1 ,7);2,078(1 ,2) ;2,073(1 ,7);2,070(1 ,9);2,062(1 ,3);2,053(1 ,0);2,047(0,7);2,044(0,8);1 ,691 (1 ,0);1 ,258(0,9 );1 ,255(0,9);0,008(0,5);0,000(16,9)  8,609 (1,8), 8,607 (2,0), 8,605 (2,0), 8,602 (1,8), 8,597 (1, 8), 8,595 (2,0), 8,593 (2,0), 8,590 (1, 8); 8.397 (7.5); 8.393 (7.4); 7.674 (1, 4); 7.670 (1, 5); 7.655 (3.2); 7.651 (3.1); 7.636 ( 7.1), 7.631 (2.0), 7.551 (9.2), 7.547 (8.9), 7.510 (2.1), 7.507 (3.5), 7.555 (2.2), 7.490 (1 , 7); 7,488 (2,8); 7,485 (1, 7); 7,323 (1,9); 7,320 (1,9); 7,31 1 (1,9); 7,308 (1,9); 7,304 (1, 8); 7,301 (1, 7); 7,292 (1, 7); 7,289 (1, 7); 7,270 (0,6); 7,265 (40,1); 5,299 (0,7); 5,180 ( 16.0), 4.162 (0.7), 4.159 (0.8), 4.155 (0.9), 4.15 2 (0.9), 4.148 (1, 0), 4.145 (1, 2); 4,137 (1, 2); 4,131 (1, 7); 4,126 (1, 2); 4,1 19 (1, 4); 4,1 16 (1, 1); 4,1 1 1 (1, 0) 4,108 (1, 0), 4,105 (0,9), 4,101 (0,8), 3,742 (0,8), 3,736 (0,9), 3,728 (0,8), 3,722 (1, 9) 3,715 (1,2), 3,713 (1,1), 3,707 (1,7), 3,701 (1,1), 3,699 (1,1), 3,692 (1, 7), 3,686 (0,8 3.678 (0.7); 3.672 (0.7); 2.288 (0.9); 2.282 (1.0); 2.273 (1.5); 2.268 (1.2); 2.261 (1); 5); 2.258 (1, 2); 2.254 (1, 6); 2.233 (1, 0); 2.234 (0.7); 2.097 (0.6); 2.093 (1, 0); 2.090 (1, 2); 2.087 (1, 2); 2.084 (1, 7); 2.078 (1, 2); 2.073 (1, 7); 2.070 (1, 9); 2.062 (1, 3); 2.053 (1, 0); 2.047 (0.7); 2.044 (0.8); 1, 691 (1, 0); 1, 258 (0.9); 1, 255 (0.9); 0.008 (0.5); 0.000 (16.9)
Beispiel No. G9-36: 1H-NMR (400 MHz, CDC δ, ppm) Example No. G9-36: 1 H-NMR (400 MHz, CDC δ, ppm)
8,660(2,2);8,657(2,2);8,491 (5,7);8,486(5,8);7,959(6,7);7,955(6,5);7,920(2,4);7,919(2,5) ;7,915(2,5);7,914(2,3);7,527(1 ,1 );7,268(201 ,9);7,218(1 ,3);7,004(1 ,1 );4,936(7,1 );3,289( 0,9);3,284(1 ,0);3,278(0,8);3,268(1 ,6);3,254(1 ,0);3,247(1 ,0);3,242(1 ,1 );2,847(0,6);2,830 (1 ,6);2,807(1 ,7);2,792(0,6);2,786(0,7);2,584(0,6);2,579(0,9);2,575(0,7);2,101 (1 ,5);2,08 8(1 ,1 );2,083(1 ,4);2,071 (0,8);1 ,924(1 ,0);1 ,906(1 ,8);1 ,898(1 ,1 );1 ,891 (0,8);1 ,718(14,2);1 , 333(0,5);1 ,290(1 ,1 );1 ,285(1 ,5);1 ,255(16,0);1 ,105(0,6);0,888(1 ,0);0,880(1 ,7);0,863(1 ,0); 0,853(1 ,0);0,836(0,9);0,008(2,0);0,000(83,9);-0,009(2,8);-0,050(0,6) Beispiel No. G9-61 : 1H-NMR (400 MHz, CDCIs δ, ppm) 8.660 (2.2), 8.657 (2.2), 8.491 (5.7), 8.486 (5.8), 7.959 (6.7), 7.955 (6.5), 7.920 (2.4), 7.919 (2.5); 7.915 (2.5); 7.914 (2.3); 7.527 (1, 1); 7.268 (201, 9); 7.218 (1, 3); 7.004 (1, 1); 4.936 ( 3.189 (0.9), 3.284 (1, 0), 3.288 (0.8), 3.268 (1, 6), 3.254 (1, 0), 3.247 (1, 0), 3.242 (1 2,847 (1, 7), 2,792 (0,6), 2,786 (0,7), 2,584 (0,6), 2,579 (0, 1), 2,847 (0,6), 2,830 (1,6); 9); 2.575 (0.7); 2.101 (1, 5); 2.08 8 (1, 1); 2.083 (1, 4); 2.071 (0.8); 1, 924 (1, 0); 1, 906 (1, 8), 1, 898 (1,1), 1,891 (0,8), 1,718 (14,2), 1,333 (0,5), 1,290 (1 , 1), 1, 285 (1, 5), 1, 255 (16.0), 1, 105 (0.6), 0.888 (1, 0), 0.880 (1, 7), 0.863 (1, 0 ); 0.853 (1.0), 0.836 (0.9), 0.008 (2.0), 0.000 (83.9), -0.009 (2.8), -0.050 (0.6) Example No. G9-61: 1 H-NMR (400 MHz, CDCIs δ, ppm)
8,433(9,7);8,429(9,9);7,745(2,5);7,742(2,4);7,741 (2,3);7,727(3,7);7,722(3,1 );7,699(2,3) ;7,696(2,8);7,679(2,9);7,677(3,2);7,598(10,7);7,594(10,9);7,591 (2,3);7,576(4,0);7,571 ( 3,6);7,557(3,1 );7,552(2,5);7,547(3,5);7,543(3,7);7,528(4,2);7,524(3,7);7,520(1 ,5);7,509 (1 ,5);7,505(1 ,3);7,262(229,6);7,212(1 ,9);6,998(1 ,2);5,354(16,0);5,300(0,6);4,226(1 ,3);4 ,217(1 ,5);4,204(2,0);4,193(1 ,6);4,183(1 ,4);3,547(0,9);3,541 (0,9);3,532(1 ,0);3,525(2,2); 3,519(1 ,5);3,51 1 (1 ,7);3,504(1 ,7);3,497(2,1 );3,482(1 ,0);3,476(0,9);2,337(0,7);2,331 (1 ,1 ) ;2,323(1 ,2);2,314(2,1 );2,302(1 ,9);2,296(1 ,9);2,285(1 ,2);2,188(0,8);2,171 (1 ,6);2,164(1 ,5 );2,151 (2,6);2,144(1 ,7);2,136(1 ,3);2,090(1 ,7);2,045(0,8);1 ,593(1 ,2);1 ,284(0,6);1 ,254(2, 4);0,008(2,6);0,000(98,4);-0,009(2,7);-0,050(0,8)  8.433 (9.7), 8.429 (9.9), 7.745 (2.5), 7.742 (2.4), 7.741 (2.3), 7.727 (3.7), 7.722 (3.1), 7.699 (2.3); 7.696 (2.8); 7.679 (2.9); 7.677 (3.2); 7.598 (10.7); 7.594 (10.9); 7.551 (2.3); 4.0), 7.571 (3.6), 7.557 (3.1), 7.552 (2.5), 7.547 (3.5), 7.543 (3.7), 7.528 (4.2), 7.524 (3 , 7); 7,520 (1, 5); 7,509 (1, 5); 7,505 (1, 3); 7,262 (229,6); 7,212 (1, 9); 6,998 (1, 2); 5,354 (16, 4, 217 (1, 5), 4.204 (2.0), 4.193 (1, 6), 4.183 (1, 4), 3.547 (0), 5,300 (0,6), 4,226 (1, 3), 4,237 (1, 5); , 9), 3.541 (0.9), 3.532 (1.0), 3.525 (2.2); 3.519 (1, 5), 3.51 1 (1, 7), 3.504 (1, 7), 3.497 (2.1), 3.482 (1.0), 3.476 (0.9), 2.379 (0.7 2,331 (1,1), 2,323 (1,2), 2,314 (2,1), 2,302 (1, 9), 2,296 (1, 9), 2,285 (1,2), 2,188 (0,8) 2,171 (1,6), 2,164 (1,5), 2,151 (2,6), 2,144 (1, 7), 2,136 (1,3), 2,090 (1,7), 2,045 (0,8); 1, 593 (1, 2); 1, 284 (0.6); 1, 254 (2, 4); 0.008 (2.6); 0.000 (98.4); - 0.009 (2.7); - 0.050 (0.8)
Beispiel No. G9-94: 1H-NMR (400 MHz, CDC δ, ppm) Example No. G9-94: 1 H-NMR (400 MHz, CDC δ, ppm)
8,423(8,4);8,419(8,6);8,376(4,5);8,371 (4,7);7,744(3,3);7,737(3,3);7,723(3,6);7,717(3,6) ;7,569(9,9);7,564(9,9);7,334(5,0);7,333(4,9);7,314(4,5);7,313(4,5);7,266(38,2);5,300(3, 6);5,102(16,0);4,186(1 ,3);4,180(1 ,5);4,172(1 ,8);4,159(2,4);4,147(1 ,9);4,137(1 ,6);3,405( 1 ,0);3,399(1 ,1 );3,390(1 ,1 );3,384(2,5);3,377(1 ,8);3,370(2,2);3,362(1 ,8);3,356(2,4);3,349 (1 ,1 );3,341 (1 ,1 );3,335(1 ,0);2,354(0,8);2,347(1 ,3);2,340(1 ,3);2,333(2,1 );2,327(1 ,8);2,31 9(2,0);2,314(2,4);2,302(1 ,4);2,294(1 ,0);2,129(0,7);2,1 16(1 ,4);2,1 1 1 (1 ,8);2,104(1 ,8);2,0 91 (2,8);2,084(2,0);2,076(1 ,5);1 ,656(1 ,7);1 ,255(0,9);0,008(0,5);0,000(16,3);-0,009(0,6)  8.423 (8.4), 8.419 (8.6), 8.376 (4.5), 8.371 (4.7), 7.744 (3.3), 7.737 (3.3), 7.723 (3.6), 7.717 (3.6), 7.569 (9.9), 7.564 (9.9), 7.334 (5.0), 7.333 (4.9), 7.314 (4.5), 7.313 (4.5), 7.266 ( 38.2); 5,300 (3, 6); 5,102 (16,0); 4,186 (1,3); 4,180 (1, 5); 4,172 (1, 8); 4,159 (2,4); 4,147 (1 , 4,137 (1,6), 3,405 (1,0), 3,399 (1,1), 3,390 (1,1), 3,384 (2,5), 3,377 (1, 8), 3,370 (2, 3,362 (1, 8), 3,356 (2,4), 3,349 (1,1), 3,341 (1,1), 3,335 (1, 0), 2,354 (0,8), 2,347 (1, 3) 2,340 (1,3), 2,333 (2,1), 2,327 (1,8), 2,31,9 (2,0), 2,314 (2,4), 2,302 (1,4), 2,294 (1 2,129 (0,7); 2,116 (1,4); 2,1 1 1 (1, 8); 2,104 (1, 8); 2,091 (2,8); 2,084 (2.0); 2.076 (1, 5); 1, 656 (1, 7); 1, 255 (0.9); 0.008 (0.5); 0.000 (16.3); - 0.009 (0, 6)
Beispiel No. G10-1 : 1H-NMR (400 MHz, CDC δ, ppm) Example No. G10-1: 1 H-NMR (400 MHz, CDC δ, ppm)
7,717(0,8);7,712(0,8);7,698(0,9);7,693(0,9);7,482(0,7);7,478(0,8);7,462(1 ,9);7,459(2,3) ;7,442(1 ,7);7,440(1 ,6);7,439(1 ,4);7,412(0,5);7,408(0,6);7,396(0,8);7,393(1 ,7);7,389(1 ,1 );7,375(2,4);7,371 (1 ,1 );7,360(0,6);7,357(1 ,1 );7,351 (0,9);7,347(0,8);7,340(0,5);7,336(1 , 0);7,332(1 ,4);7,328(1 ,0);7,318(0,9);7,261 (13,3);6,986(5,2);5,394(4,8);5,296(1 ,9);5,095( 4,6);3,432(16,0);0,000(5,9)  7.717 (0.8), 7.712 (0.8), 7.698 (0.9), 7.693 (0.9), 7.482 (0.7), 7.478 (0.8), 7.462 (1.9), 7.459 (2.3); 7.442 (1, 7); 7.440 (1, 6); 7.439 (1, 4); 7.412 (0.5); 7.408 (0.6); 7.396 (0.8); 7.393 ( 1, 7), 7.389 (1, 1), 7.375 (2.4), 7.371 (1, 1), 7.360 (0.6), 7.357 (1, 1), 7.351 (0.9), 7.347 (0 , 8,3); 7,340 (0.5); 7,336 (1, 0); 7,332 (1, 4); 7,328 (1, 0); 7,318 (0,9); 7,261 (13,3); 6,986 (5, 5); 2), 5.394 (4.8), 5.296 (1, 9), 5.095 (4.6), 3.432 (16.0), 0.000 (5.9)
Beispiel No. G10-3: 1H-NMR (400 MHz, CDCb δ, ppm) Example No. G10-3: 1 H-NMR (400 MHz, CDCb δ, ppm)
7,461 (0,9);7,457(1 ,2);7,440(1 ,9);7,439(1 ,8);7,437(1 ,6);7,432(0,6);7,41 1 (5,2);7,405(5,5) ;7,396(0,9);7,393(1 ,1 );7,388(0,5);7,385(0,5);7,383(0,6);7,380(0,6);7,375(2,2);7,371 (0,9 );7,360(0,7);7,357(1 ,2);7,337(0,9);7,319(0,9);7,261 (15,4);6,969(5,3);5,390(5,1 );5,297(2 ,0);4,830(4,7);3,361 (16,0);2,075(0,7);0,000(6,6) Beispiel No. G10-4: 1H-NMR (400 MHz, CDCIs δ, ppm) 7.461 (0.9); 7.457 (1, 2); 7.440 (1, 9); 7.439 (1, 8); 7.437 (1, 6); 7.432 (0.6); 7.41 (5.2 7.405 (5.5), 7.396 (0.9), 7.393 (1, 1), 7.388 (0.5), 7.385 (0.5), 7.383 (0.6), 7.380 (0.6) 7.375 (2.2); 7.371 (0.9); 7.360 (0.7); 7.357 (1, 2); 7.379 (0.9); 7.319 (0.9); 7.261 (15.4); 6.969 (5.3), 5.390 (5.1), 5.297 (2, 0), 4.830 (4.7), 3.361 (16.0), 2.075 (0.7), 0.000 (6.6) Example No. G10-4: 1 H-NMR (400 MHz, CDCIs δ, ppm)
7,653(0,8);7,650(0,9);7,634(1 ,0);7,630(1 ,0);7,580(1 ,0);7,576(0,9);7,560(1 ,2);7,556(1 ,0) ;7,461 (0,9);7,457(1 ,3);7,440(1 ,9);7,439(1 ,9);7,396(0,7);7,393(1 ,1 );7,375(2,3);7,371 (1 ,0 );7,360(0,7);7,357(1 ,2);7,341 (0,6);7,337(1 ,0);7,334(0,5);7,319(1 ,0);7,295(1 ,0);7,275(1 , 6);7,261 (17,7);7,256(0,8);6,982(2,3);5,391 (5,5);5,297(0,8);5,154(5,2);3,444(16,0);2,06 5(0,9);2,044(0,6);1 ,258(0,6);0,000(7,5)  7.653 (0.8), 7.650 (0.9), 7.634 (1.0), 7.630 (1.0), 7.580 (1.0), 7.576 (0.9), 7.560 (1.2), 7.556 (1, 0); 7,461 (0.9); 7,457 (1,3), 7,440 (1,9), 7,439 (1,9), 7,396 (0,7), 7,393 (1,1), 7,375 ( 2.3); 7.371 (1, 0); 7.360 (0.7); 7.357 (1, 2); 7.341 (0.6); 7.337 (1, 0); 7.334 (0.5); 7.319 (1 7,295 (1, 0), 7.275 (1, 6), 7.261 (17.7), 7.256 (0.8), 6.982 (2.3), 5.391 (5.5), 5.297 (0, 8); 5.154 (5.2); 3.444 (16.0); 2.06 5 (0.9); 2.044 (0.6); 1, 258 (0.6); 0.000 (7.5)
Beispiel No. G10-1 1 : 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. G10-1 1: 1 H NMR (400 MHz, CDCIs δ, ppm)
7,603(0,6);7,599(0,6);7,584(1 ,2);7,580(1 ,2);7,566(0,7);7,561 (0,7);7,463(1 ,0);7,460(1 ,8) ;7,456(2,2);7,450(1 ,1 );7,443(2,2);7,439(3,2);7,438(3,1 );7,429(0,8);7,425(0,5);7,394(1 ,1 );7,391 (1 ,6);7,386(0,6);7,373(3,4);7,369(1 ,5);7,358(1 ,0);7,355(1 ,8);7,338(0,8);7,334(1 , 4);7,331 (0,8);7,317(1 ,4);7,261 (20,4);7,235(1 ,0);7,232(1 ,0);7,216(1 ,6);7,213(1 ,7);7,197( 0,8);7,194(0,8);7,177(0,8);7,174(0,8);7,156(0,8);7,152(1 ,1 );7,149(0,8);7,131 (0,7);7,128 (0,7);6,977(9,3);5,389(7,8);5,297(1 ,1 );4,963(4,8);3,403(15,9);3,401 (16,0);2,069(1 ,0);0, 000(8,6) 7.603 (0.6); 7.599 (0.6); 7.584 (1, 2); 7.580 (1, 2); 7.566 (0.7); 7.561 (0.7); 7.463 (1, 0); 7.460 (1, 8); 7.456 (2.2); 7.450 (1, 1); 7.443 (2.2); 7.499 (3.2); 7.438 (3.1); 7.429 (0.8); 7.425 ( 7.359 (1, 1), 7.391 (1, 6), 7.399 (1, 6), 7.399 (1, 6), 7.399 (1, 6), 7.399 (1, 6), 7.399 (1, 6), 7.369 (1, 5), 7.359 (1, 6); , 7,338 (0,8), 7,317 (1,4), 7,261 (20,4), 7,235 (1, 0), 7,232 (1, 4); 7.216 (1, 6), 7.213 (1, 7), 7.197 (0.8), 7.194 (0.8), 7.177 (0.8), 7.174 (0.8), 7.156 (0.8 7.152 (1, 1), 7.149 (0.8), 7.131 (0.7), 7.128 (0.7), 6.977 (9.3), 5.389 (7.8), 5.297 (1, 1) 4.963 (4.8), 3.403 (15.9), 3.401 (16.0), 2.069 (1, 0), 0, 000 (8.6)
Beispiel No. G10-15: 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. G10-15: 1 H-NMR (400 MHz, CDCIs δ, ppm)
7,631 (0,6);7,615(0,6);7,610(1 ,1 );7,594(1 ,1 );7,588(0,6);7,572(0,6);7,459(1 ,3);7,455(1 ,8) ;7,450(0,6);7,439(2,8);7,437(2,6);7,435(2,3);7,396(1 ,1 );7,392(1 ,6);7,387(0,6);7,379(0,7 );7,374(3,4);7,370(1 ,4);7,360(0,9);7,356(1 ,8);7,340(0,8);7,336(1 ,4);7,333(0,7);7,319(1 , 4);7,261 (24,4);6,974(0,5);6,972(0,6);6,965(9,5);6,959(0,9);6,953(1 ,0);6,931 (1 ,2);6,924( 0,5);6,909(0,8);6,905(0,9);6,899(0,6);6,884(0,7);6,877(0,6);5,387(7,9);5,297(2,1 );4,913 7.631 (0.6), 7.615 (0.6), 7.610 (1, 1), 7.594 (1, 1), 7.588 (0.6), 7.572 (0.6), 7.459 (1, 3), 7.455 (1, 8), 7.450 (0.6), 7.439 (2.8), 7.437 (2.6), 7.435 (2.3), 7.396 (1, 1), 7.392 (1, 6), 7.387 ( 7.369 (0.7); 7.379 (0.7); 7.374 (3.4); 7.370 (1.4); 7.366 (0.9); 7.356 (1.8); 7.340 (0.8); 7.336 (1 7,333 (0.7); 7,319 (1, 4); 7,261 (24.4); 6,974 (0.5); 6,972 (0.6); 6,965 (9,5); 6,959 (0); 9), 6.953 (1, 0), 6.931 (1.2), 6.924 (0.5), 6.909 (0.8), 6.905 (0.9), 6.899 (0.6), 6.884 (0.7 6.877 (0.6), 5.387 (7.9), 5.297 (2.1), 4.913
(4.4) ;3,401 (15,9);3,399(16,0);2,073(1 ,5);2,044(1 ,0);1 ,258(0,8);0,000(10,3) (4.4); 3.401 (15.9); 3.399 (16.0); 2.073 (1, 5); 2.044 (1, 0); 1, 258 (0.8); 0.000 (10.3)
Beispiel No. G10-21 : 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. G10-21: 1 H-NMR (400 MHz, CDCIs δ, ppm)
8,639(0,6);8,637(0,6);8,635(0,6);8,633(0,6);8,627(0,6);8,625(0,6);8,623(0,6);8,620(0,6) ;7,742(1 ,0);7,738(0,9);7,723(0,7);7,719(0,6);7,643(0,7);7,640(1 ,1 );7,638(0,7);7,624(0,5 );7,621 (0,8);7,454(0,7);7,450(1 ,0);7,437(0,7);7,434(1 ,5);7,432(1 ,4);7,431 (1 ,3);7,392(0, 6);7,389(0,9);7,371 (1 ,9);7,367(0,9);7,365(0,7);7,362(0,6);7,356(0,6);7,353(1 ,5);7,346(0 ,6);7,343(0,6);7,334(1 ,2);7,331 (0,8);7,315(0,7);7,261 (17,5);6,955(5,3);5,381 (4,2);4,998 8,639 (0.6); 8.637 (0.6); 8,635 (0.6); 8.633 (0.6); 8,627 (0.6); 8,625 (0.6); 8,623 (0.6); 8,620 (0.6); 7.742 (1.0); 7.738 (0.9); 7.723 (0.7); 7.719 (0.6); 7.643 (0.7); 7.640 (1, 1); 7.638 (7.638). 0.7), 7.624 (0.5), 7.621 (0.8), 7.454 (0.7), 7.450 (1, 0), 7.437 (0.7), 7.434 (1.5), 7.432 (1 , 4); 7,431 (1,3), 7,392 (0, 6), 7,389 (0,9), 7,371 (1, 9), 7,367 (0,9), 7,365 (0,7), 7,362 (0, 6), 7.356 (0.6), 7.353 (1, 5), 7.346 (0, 6), 7.343 (0.6), 7.334 (1, 2), 7.331 (0.8), 7.315 (0.7 7.261 (17.5), 6.955 (5.3), 5.381 (4.2), 4.998
(4.5) ;3,468(16,0);1 ,624(1 ,9);0,000(7,6) Beispiel No. G10-36: 1H-NMR (400 MHz, CDCIs δ, ppm) (4.5); 3.468 (16.0); 1, 624 (1, 9); 0.000 (7.6) Example No. G10-36: 1 H-NMR (400 MHz, CDCls δ, ppm)
8,667(0,7);8,664(0,7);7,919(0,7);7,918(0,8);7,914(0,7);7,913(0,7);7,465(0,5);7,461 (0,7) ;7,444(1 ,1 );7,442(1 ,0);7,441 (0,9);7,397(0,7);7,379(1 ,4);7,375(0,6);7,361 (0,7);7,352(4,8 );7,341 (0,6);7,323(0,6);7,265(0,8);7,259(83,1 );7,256(1 ,1 );7,255(0,7);5,392(3,1 );4,932(2 ,0);2,690(14,6);1 ,537(16,0);0,008(1 ,0);0,002(1 ,2);0,000(35,1 );-0,009(1 ,0)  8,667 (0.7); 8,664 (0.7); 7.919 (0,7) 7.918 (0.8); 7.914 (0,7) 7.913 (0.7); 7.465 (0,5); 7,461 (0.7); 7.444 (1, 1); 7.442 (1, 0); 7.441 (0.9); 7.397 (0.7); 7.379 (1, 4); 7.375 (0.6); 7.361 ( 0.7), 7.352 (4.8), 7.341 (0.6), 7.323 (0.6), 7.265 (0.8), 7.259 (83.1), 7.256 (1, 1), 7.255 (0 , 7); 5,392 (3,1); 4,932 (2, 0); 2,690 (14,6); 1, 537 (16,0); 0.008 (1, 0); 0.002 (1, 2); 0.000 ( 35.1), - 0.009 (1, 0)
Beispiel No. G10-61 : 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. G10-61: 1 H-NMR (400 MHz, CDCIs δ, ppm)
7,862(0,7);7,860(0,7);7,842(0,9);7,840(0,9);7,769(0,7);7,766(0,7);7,750(0,9);7,747(0,9) ;7,670(1 ,0);7,666(0,9);7,650(0,6);7,646(0,5);7,594(0,8);7,591 (0,8);7,575(1 ,1 );7,572(1 ,1 );7,461 (0,8);7,457(1 ,1 );7,444(0,8);7,441 (1 ,7);7,439(1 ,6);7,437(1 ,4);7,398(0,7);7,394(1 , 0);7,377(2,1 );7,373(0,8);7,362(0,6);7,359(1 ,1 );7,339(0,9);7,322(0,8);7,261 (14,1 );6,981 ( 5,7);5,390(4,8);5,297(3,0);5,1 15(4,1 );3,490(16,0);2,070(0,7);2,043(0,6);0,000(6,1 )  7,862 (0.7); 7,860 (0.7); 7,842 (0.9); 7,840 (0.9); 7,769 (0.7); 7,766 (0.7); 7,750 (0.9); 7.747 7.666 (0.9); 7.650 (0.6); 7.646 (0.5); 7.594 (0.8); 7.591 (0.8); 7.575 (7.966 (0.9); 1, 1); 7,572 (1, 1); 7,461 (0.8); 7,457 (1, 1); 7,444 (0.8); 7,441 (1, 7); 7,439 (1, 6); 7,437 (1 7,398 (0,7); 7,394 (1, 0); 7,377 (2,1); 7,373 (0,8); 7,362 (0,6); 7,359 (1, 1); 7,339 (0); 9); 7,322 (0.8); 7,261 (14.1); 6,981 (5,7); 5,390 (4,8); 5,297 (3,0); 5,1 15 (4,1); 3,490 ( 16.0), 2.070 (0.7), 2.043 (0.6), 0.000 (6.1)
Beispiel No. G10-94: 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. G10-94: 1 H-NMR (400 MHz, CDCl3 δ, ppm)
8,423(1 ,4);8,417(1 ,4);7,902(0,9);7,896(0,9);7,882(0,9);7,875(0,9);7,461 (0,9);7,457(1 ,3) ;7,440(1 ,9);7,439(1 ,8);7,407(1 ,5);7,399(0,8);7,395(1 ,1 );7,390(0,5);7,387(1 ,5);7,378(2,3 );7,374(1 ,0);7,363(0,7);7,360(1 ,2);7,344(0,5);7,340(1 ,0);7,337(0,5);7,323(0,9);7,265(10 ,5);6,957(5,4);5,386(5,4);4,830(4,3);4,748(5,1 );3,416(16,0);1 ,707(1 ,6);0,000(4,1 ) Beispiel No. G1 1 -1 : 1H-NMR (400 MHz, CDCIs δ, ppm) 8.423 (1, 4), 8.417 (1, 4), 7.902 (0.9), 7.896 (0.9), 7.882 (0.9), 7.875 (0.9), 7.461 (0.9), 7.457 (1, 3); 7,440 (1, 9); 7,439 (1, 8); 7,407 (1, 5); 7,399 (0.8); 7,395 (1, 1); 7,390 (0.5); 7,387 ( 1, 5); 7,378 (2,3); 7,374 (1, 0); 7,363 (0.7); 7,360 (1, 2); 7,344 (0.5); 7,340 (1, 0); 7,337 (0 , 7,323 (0.9), 7.265 (10, 5), 6.957 (5.4), 5.386 (5.4), 4.830 (4.3), 4.748 (5.1), 3.416 (16, 0); 1, 707 (1, 6); 0.000 (4.1) Example no. G1 1 -1: 1 H NMR (400 MHz, CDCl3 δ, ppm)
7,738(0,8);7,734(0,7);7,719(0,9);7,715(0,8);7,481 (0,7);7,477(0,8);7,466(0,9);7,461 (1 ,8) ;7,457(1 ,5);7,449(0,8);7,447(1 ,1 );7,446(1 ,6);7,444(1 ,5);7,442(1 ,3);7,410(0,6);7,406(0,6 );7,393(0,8);7,391 (1 ,6);7,387(1 ,1 );7,372(2,5);7,369(1 ,1 );7,358(0,6);7,354(1 ,1 );7,350(0, 9);7,346(0,8);7,332(1 ,2);7,328(1 ,4);7,312(1 ,0);7,31 1 (1 ,0);7,260(20,8);5,426(4,3);5,297( 0,7);5,124(4,3);3,437(15,5);2,350(16,0);2,043(0,9);1 ,588(0,5);1 ,258(0,7);0,000(8,6)  7.738 (0.8), 7.734 (0.7), 7.719 (0.9), 7.715 (0.8), 7.481 (0.7), 7.477 (0.8), 7.466 (0.9), 7.461 (1, 8); 7,457 (1, 5); 7,449 (0.8); 7,447 (1, 1); 7,446 (1,6); 7,444 (1, 5); 7,442 (1, 3); 7,410 ( 7.406 (0.6), 7.406 (0.6), 7.393 (0.8), 7.391 (1, 6), 7.387 (1, 1), 7.372 (2.5), 7.369 (1, 1), 7.358 (0 7,354 (1, 1), 7,350 (0, 9), 7,346 (0,8), 7,332 (1,2), 7,328 (1,4), 7,312 (1, 0), 7,31 1 (1, 0); 7.260 (20.8); 5.426 (4.3); 5.297 (0.7); 5.124 (4.3); 3.437 (15.5); 2.350 (16.0); 2.043 ( 0.9); 1, 588 (0.5); 1, 258 (0.7); 0.000 (8.6)
Beispiel No. G1 1 -3: 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. G1 1 -3: 1 H-NMR (400 MHz, CDCls δ, ppm)
7,464(0,8);7,460(1 ,2);7,443(1 ,8);7,441 (2,2);7,435(0,6);7,425(0,7);7,419(3,9);7,415(0,9) ;7,409(1 ,1 );7,405(4,3);7,399(0,7);7,393(0,7);7,389(1 ,5);7,385(1 ,0);7,383(1 ,1 );7,372(2,1 );7,368(0,9);7,357(0,6);7,354(1 ,1 );7,329(0,8);7,31 1 (0,9);7,261 (15,6);5,422(4,3);5,296(3 ,1 );4,857(4,4);3,363(16,0);2,336(15,4);2,043(0,9);1 ,258(0,7);0,000(6,7) Beispiel No. G1 1 -4: 1H-NMR (400 MHz, CDCIs δ, ppm) 7.444 (0.8), 7.460 (1.2), 7.443 (1, 8), 7.441 (2.2), 7.435 (0.6), 7.425 (0.7), 7.419 (3.9), 7.415 7.499 (0.7), 7.399 (0.7), 7.399 (1, 5), 7.389 (1, 1), 7.409 (1, 1), 7.405 (4.3), 7.399 (0.7), 7.393 (0.7), 7.389 (1, 5), 7.385 (1, 0), 7.383 ( 1, 1), 7.372 (2.1), 7.368 (0.9), 7.357 (0.6), 7.354 (1, 1), 7.329 (0.8), 7.31 1 (0.9); 7.261 (15.6), 5.422 (4.3), 5.296 (3, 1), 4.857 (4.4), 3.363 (16.0), 2.336 (15.4), 2.043 (0.9), 1 , 258 (0.7); 0,000 (6.7) Example No. G1 1 -4: 1 H-NMR (400 MHz, CDCl3 δ, ppm)
7,675(1 ,0);7,671 (1 ,1 );7,656(1 ,1 );7,652(1 ,1 );7,577(1 ,2);7,573(1 ,2);7,557(1 ,5);7,553(1 ,3) ;7,464(0,9);7,460(1 ,2);7,447(0,8);7,445(1 ,2);7,444(1 ,8);7,442(1 ,7);7,440(1 ,5);7,393(0,7 );7,390(1 ,1 );7,372(2,2);7,368(1 ,0);7,357(0,6);7,354(1 ,1 );7,330(0,9);7,31 1 (0,9);7,294(1 , 6);7,274(2,1 );7,261 (1 1 ,3);7,254(1 ,1 );5,423(4,7);5,295(4,8);5,178(4,6);3,445(16,0);2,34 2(16,0);0,000(4,9)  7.675 (1, 0), 7.671 (1, 1), 7.656 (1, 1), 7.652 (1, 1), 7.577 (1, 2), 7.573 (1, 2), 7.557 (1, 5), 7.553 (1, 3); 7,464 (0,9); 7,460 (1, 2); 7,447 (0.8); 7,445 (1, 2); 7,444 (1, 8); 7,442 (1, 7); 7,440 ( 1, 5), 7,393 (0.7), 7,390 (1,1), 7,372 (2,2), 7,368 (1, 0), 7,357 (0,6), 7,354 (1,1), 7,330 (0 , 9), 7.31 1 (0.9), 7.294 (1, 6), 7.274 (2.1), 7.261 (1, 1, 3), 7.254 (1, 1), 5.433 (4.7); 5.295 (4.8), 5.178 (4.6), 3.445 (16.0), 2.34 2 (16.0), 0.000 (4.9)
Beispiel No. G1 1 -1 1 : 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. G1 1 -1 1: 1 H-NMR (400 MHz, CDCIs δ, ppm)
7,604(0,7);7,599(0,8);7,463(1 ,0);7,461 (1 ,3);7,459(1 ,6);7,455(0,7);7,442(2,0);7,441 (2,2) ;7,391 (0,7);7,388(1 ,1 );7,371 (2,2);7,367(0,9);7,355(0,6);7,352(1 ,1 );7,327(0,9);7,309(0,9 );7,260(18,8);7,234(0,6);7,231 (0,7);7,215(1 ,0);7,212(1 ,1 );7,193(0,5);7,176(0,5);7,151 (0 ,7);7,148(0,5);5,422(4,6);4,992(2,9);3,406(9,7);3,404(9,9);2,341 (16,0);1 , 586(1 ,9);0,000 (8,2) Beispiel No. G1 1 -15: 1H-NMR (400 MHz, CDCIs δ, ppm) 7.604 (0.7), 7.599 (0.8), 7.463 (1, 0), 7.461 (1.3), 7.459 (1.6), 7.455 (0.7), 7.442 (2.0), 7.441 (2.2), 7.391 (0.7), 7.388 (1, 1), 7.371 (2.2), 7.367 (0.9), 7.355 (0.6), 7.352 (1, 1), 7.327 ( 7.29 (0.9), 7.260 (18.8), 7.234 (0.6), 7.231 (0.7), 7.215 (1, 0), 7.212 (1, 1), 7.193 (0 7,176 (0.5), 7,151 (0, 7), 7,148 (0.5), 5,422 (4,6), 4,992 (2,9), 3,406 (9,7), 3,404 (9, 9); 2.341 (16.0); 1, 586 (1, 9); 0.000 (8.2) Example no. G1 1 -15: 1 H-NMR (400 MHz, CDCl3 δ, ppm)
7,631 (0,7);7,615(0,7);7,462(0,9);7,459(1 ,2);7,443(1 ,2);7,442(1 ,8);7,440(1 ,7);7,438(1 ,4) ;7,392(0,7);7,389(1 ,1 );7,371 (2,2);7,367(0,9);7,356(0,6);7,353(1 ,1 );7,329(0,8);7,31 1 (0,9 );7,261 (20,6);6,951 (0,6);6,929(0,7);6,903(0,5);5,419(4,5);5,297(0,8);4,940(2,6);4,939(2 ,6);3,404(9,9);3,401 (9,8);2,341 (0,8);2,330(16,0);1 ,590(2,9);0,000(9,0)  7.631 (0.7); 7.615 (0.7); 7.462 (0.9); 7.459 (1, 2); 7.433 (1, 2); 7.442 (1, 8); 7.440 (1, 7); 7.438 (1, 4); 7.392 (0.7); 7.389 (1, 1); 7.371 (2.2); 7.367 (0.9); 7.356 (0.6); 7.353 (1, 1); 0.8); 7.31 1 (0.9); 7.261 (20.6); 6.951 (0.6); 6.929 (0.7); 6.903 (0.5); 5.419 (4.5); 5.997 (0.8); 4.940 (2.6); 4.939 (2, 6); 3.404 (9.9); 3.401 (9.8); 2.341 (0.8); 2.330 (16.0); 1 , 590 (2.9); 0,000 (9.0)
Beispiel No. G1 1 -21 : 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. G1 1 -21: 1 H-NMR (400 MHz, CDCls δ, ppm)
8,639(0,6);8,637(0,6);8,635(0,7);8,632(0,6);8,627(0,6);8,625(0,6);8,623(0,6);8,620(0,6) ;7,742(0,9);7,738(0,9);7,723(0,7);7,719(0,7);7,668(0,7);7,665(1 ,1 );7,663(0,7);7,646(0,7 );7,456(0,7);7,452(1 ,0);7,436(1 ,5);7,434(1 ,5);7,432(1 ,3);7,389(0,6);7,385(1 ,0);7,368(1 , 9);7,364(1 ,4);7,361 (0,7);7,352(1 ,0);7,349(1 ,5);7,345(0,7);7,342(0,6);7,333(0,6);7,330(0 ,8);7,325(0,8);7,307(0,8);7,262(12,7);5,41 1 (4,0);5,018(4,5);3,476(16,0);3,468(0,6);2,30 7(14,1 );2,080(0,9);2,043(0,6);1 ,258(0,6);0,000(5,3)  8,639 (0.6); 8.637 (0.6); 8,635 (0.7); 8,632 (0.6); 8,627 (0.6); 8,625 (0.6); 8,623 (0.6); 8,620 (0.6), 7.742 (0.9), 7.738 (0.9), 7.723 (0.7), 7.719 (0.7), 7.668 (0.7), 7.665 (1, 1), 7.663 ( 7.466 (0.7), 7.466 (0.7), 7.456 (0.7), 7.452 (1, 0), 7.436 (1.5), 7.434 (1.5), 7.432 (1.3), 7.389 (0 , 6); 7,385 (1, 0); 7,368 (1, 9); 7,364 (1, 4); 7,361 (0,7); 7,352 (1, 0); 7,349 (1, 5); 7,345 (0); 7); 7,342 (0.6); 7,333 (0,6); 7,330 (0, 8); 7,325 (0.8); 7,307 (0.8); 7,262 (12,7); 5,41 1 ( 4.0), 5.018 (4.5), 3.476 (16.0), 3.468 (0.6), 2.30 7 (14.1), 2.080 (0.9), 2.043 (0.6); 1, 258 (0.6); 0.000 (5.3)
Beispiel No. G1 1 -36: 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. G1 1 -36: 1 H-NMR (400 MHz, CDCIs δ, ppm)
8,836(0,9);8,834(1 ,0);8,831 (1 ,0);8,829(0,9);8,068(1 ,0);8,067(1 ,0);8,063(1 ,0);8,062(0,9) ;7,452(0,8);7,449(1 ,1 );7,435(0,7);7,432(1 ,6);7,430(1 ,5);7,428(1 ,3);7,386(0,7);7,383(1 ,0 );7,365(2,0);7,361 (0,9);7,350(0,6);7,347(1 ,0);7,323(0,8);7,305(0,8);7,265(0,6);7,264(0, 8);7,260(36,2);5,410(4,1 );5,266(3,9);3,628(16,0);2,318(14,7);2,083(0,6);1 ,256(0,6);0,0 02(0,6);0,000(15,9) 8.836 (0.9), 8.834 (1.0), 8.831 (1.0), 8.829 (0.9), 8.068 (1.0), 8.067 (1.0), 8.063 (1.0), 8.062 7.492 (0.7); 7.432 (1, 6); 7.430 (1, 5); 7.428 (1, 3); 7.386 (1, 7); 7,383 (1, 0); 7,365 (2,0); 7,361 (0.9); 7,350 (0.6); 7,347 (1, 0); 7,323 (0.8); 7,305 (0 , 8); 7,265 (0.6); 7,264 (0, 8), 7.260 (36.2), 5.410 (4.1), 5.266 (3.9), 3.628 (16.0), 2.318 (14.7), 2.083 (0.6), 1.256 (0 , 6) 0,0 02 (0,6); 0,000 (15,9)
Beispiel No. G1 1 -61 : 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. G1 1 -61: 1 H-NMR (400 MHz, CDCl3 δ, ppm)
7,892(0,7);7,890(0,8);7,872(0,9);7,870(0,9);7,766(0,7);7,763(0,8);7,746(0,9);7,744(0,9) ;7,685(0,5);7,669(1 ,0);7,666(0,9);7,650(0,7);7,646(0,6);7,590(0,8);7,587(0,8);7,571 (1 ,1 );7,568(1 ,1 );7,464(0,8);7,460(1 ,2);7,444(1 ,7);7,442(1 ,6);7,440(1 ,4);7,395(0,7);7,392(1 , 0);7,374(2,1 );7,370(0,9);7,359(0,6);7,356(1 ,1 );7,332(0,8);7,314(0,9);7,261 (14,0);5,422( 4,5);5,297(1 ,3);5,145(4,1 );3,490(16,0);2,334(15,5);1 ,607(0,6);0,000(5,7) 7,892 (0.7); 7,890 (0.8); 7,872 (0.9); 7,870 (0.9); 7,766 (0.7); 7,763 (0.8); 7.746 (0.9); 7.744 7.666 (0.9), 7.650 (0.7), 7.646 (0.6), 7.590 (0.8), 7.586 (0.9) 7.5), 7.571 (1, 1), 7.568 (1, 1), 7.444 (0.8), 7.460 (1.2), 7.444 (1, 7), 7.442 (1, 6), 7.440 (1 , 4); 7,395 (0.7); 7,392 (1, 0); 7,374 (2,1); 7,370 (0,9); 7,359 (0,6); 7,356 (1, 1); 7,332 (0); 8), 7.314 (0.9), 7.261 (14.0), 5.422 (4.5), 5.297 (1, 3), 5.145 (4.1), 3.490 (16.0), 2.334 (15.5 ), 1, 607 (0.6), 0.000 (5.7)
Beispiel No. G1 1 -94: 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. G1 1 -94: 1 H-NMR (400 MHz, CDCIs δ, ppm)
8,423(1 ,1 );8,422(1 ,2);8,417(1 ,2);8,416(1 ,2);7,926(0,9);7,920(0,9);7,905(1 ,0);7,899(1 ,0) ;7,464(0,8);7,461 (1 ,2);7,447(0,8);7,445(1 ,1 );7,444(1 ,7);7,442(1 ,6);7,440(1 ,4);7,406(1 ,4 );7,405(1 ,4);7,396(0,7);7,393(1 ,1 );7,386(1 ,4);7,384(1 ,4);7,375(2,1 );7,371 (0,9);7,360(0, 6);7,357(1 ,0);7,333(0,8);7,315(0,8);7,262(17,1 );5,419(4,3);5,298(1 ,4);4,863(3,8);3,421 ( 15,9);2,322(16,0);2,072(0,6);2,044(1 ,9);1 ,276(0,6);1 ,258(1 ,5);1 ,240(0,6);0,000(7,7)  8.423 (1, 1), 8.422 (1, 2), 8.417 (1, 2), 8.416 (1, 2), 7.926 (0.9), 7.920 (0.9), 7.905 (1, 0), 7.899 (1, 0); 7.464 (0.8); 7.461 (1, 2); 7.447 (0.8); 7.445 (1, 1); 7.444 (1, 7); 7.442 (1, 6); 7.440 ( 1, 4), 7,406 (1,4), 7,405 (1,4), 7,396 (0,7), 7,393 (1,1), 7,386 (1,4), 7,384 (1,4), 7,375 (2 7.371 (0.9), 7.367 (0.6), 7.357 (1, 0), 7.333 (0.8), 7.315 (0.8), 7.262 (17.1), 5.419 (4, 3); 5,298 (1,4), 4,863 (3,8), 3,421 (15,9), 2,322 (16,0), 2,072 (0,6), 2,044 (1, 9), 1, 276 (0 , 6); 1, 258 (1, 5); 1, 240 (0.6); 0.000 (7.7)
Beispiel No. H1 -1 : 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. H1 -1: 1 H-NMR (400 MHz, CDCl3 δ, ppm)
8,974(4,3);7,669(0,7);7,665(0,7);7,650(0,8);7,646(0,8);7,504(0,6);7,501 (0,7);7,484(1 ,0) ;7,480(1 ,0);7,420(0,5);7,416(0,5);7,402(0,8);7,397(0,8);7,382(0,6);7,377(0,5);7,337(0,7 );7,334(0,7);7,318(0,9);7,315(0,9);7,266(13,9);5,302(1 ,2);5,288(4,4);3,488(16,0);0,000( 5,8)  7.665 (0.8); 7.646 (0.8); 7.504 (0.6); 7.551 (0.7); 7.484 (1, 0); 7,480 (1, 0); 7,420 (0.5); 7,416 (0.5); 7,402 (0.8); 7,397 (0.8); 7,382 (0.6); 7,377 ( 7.373 (0.9), 7.315 (0.9), 7.266 (13.9), 5.302 (1, 2), 5.288 (4 , 4); 3,488 (16,0); 0,000 (5,8)
Beispiel No. H1 -3: 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. H1 -3: 1 H-NMR (400 MHz, CDCl3 δ, ppm)
8,943(4,5);7,445(0,8);7,429(0,6);7,423(3,7);7,419(0,9);7,414(0,9);7,410(3,9);7,404(0,6) ;7,390(0,6);7,388(0,8);7,270(7,5);5,301 (5,0);5,018(4,5);3,420(16,0);2,045(1 ,6);1 ,259(1 , 0);0,000(3,1 ) 8,943 (4.5); 7,445 (0.8); 7.429 (0.6); 7,423 (3.7); 7,419 (0.9); 7,414 (0.9); 7,410 (3.9); 7,404 (0.6); 7.390 (0.6); 7.388 (0.8); 7.270 (7.5); 5.301 (5.0); 5.018 (4.5); 3.420 (16.0); 2.045 ( 1, 6); 1, 259 (1, 0); 0.000 (3.1)
Beispiel No. H1 -4: 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. H1 -4: 1 H-NMR (400 MHz, CDCIs δ, ppm)
8,958(4,6);7,61 1 (0,8);7,607(1 ,0);7,591 (0,9);7,587(1 ,4);7,586(1 ,5);7,582(0,9);7,565(1 ,4) ;7,561 (0,9);7,277(1 ,2);7,268(10,6);7,257(1 ,7);7,238(0,9);5,348(4,7);5,303(4,2);3,497(1 6,0);2,047(0,5);0,000(4,5) Beispiel No. H1 -1 1 : 1H-NMR (400 MHz, CDCIs δ, ppm) 8.958 (4.6), 7.61 (0.8), 7.607 (1, 0), 7.551 (0.9), 7.587 (1, 4), 7.586 (1, 5), and 7.582 (0.9) 7.565 (1, 4); 7.561 (0.9); 7.277 (1, 2); 7.268 (10.6); 7.257 (1, 7); 7.238 (0.9); 5.338 (4.7); 5.303 (4.2); 3.497 (1 6.0); 2.047 (0.5); 0.000 (4.5) Example No. H1 -1 1: 1 H-NMR (400 MHz, CDCIs δ, ppm)
8,960(8,9);7,575(0,5);7,571 (0,6);7,556(1 ,1 );7,552(1 ,2);7,537(0,6);7,533(0,7);7,473(0,8) ;7,471 (0,6);7,468(0,5);7,466(0,5);7,459(0,6);7,457(0,6);7,454(0,6);7,452(0,8);7,438(0,5 );7,269(16,8);7,224(0,9);7,222(1 ,1 );7,206(1 ,5);7,203(2,0);7,196(0,9);7,187(0,7);7,184(0 ,9);7,176(0,8);7,172(1 ,1 );7,169(0,8);7,151 (0,7);7,148(0,6);5,303(4,0);5,150(4,7);5,148( 4,6);3,461 (15,9);3,458(16,0);1 ,724(0,6);0,000(7,1 )  8.960 (8.9), 7.575 (0.5), 7.571 (0.6), 7.556 (1, 1), 7.552 (1.2), 7.537 (0.6), 7.533 (0.7), 7.473 (0.8); 7.471 (0.6); 7.468 (0.5); 7.466 (0.5); 7.459 (0.6); 7.457 (0.6); 7.454 (0.6); 7.452 ( 7.438 (0.5), 7.269 (16.8), 7.224 (0.9), 7.222 (1, 1), 7.206 (1.5), 7.203 (2.0), 7.196 (0 7,187 (0,7); 7,172 (1, 1); 7,169 (0,8); 7,151 (0,7); 7,148 (0, 7,148 (0, 9); 6), 5.303 (4.0), 5.150 (4.7), 5.148 (4.6), 3.461 (15.9), 3.458 (16.0), 1, 724 (0.6), 0.000 (7 ,1 )
Beispiel No. H1 -21 : 1H-NMR (400 MHz, CDC δ, ppm) Example No. H1 -21: 1 H-NMR (400 MHz, CDC δ, ppm)
8,922(4,0);8,657(0,6);8,655(0,6);8,653(0,5);8,647(0,5);8,645(0,6);8,643(0,6);7,725(0,9) ;7,721 (0,9);7,706(0,6);7,701 (0,6);7,621 (0,6);7,618(1 ,0);7,616(0,6);7,599(0,7);7,365(0,5 );7,362(0,5);7,353(0,5);7,350(0,5);7,346(0,5);7,271 (7,4);5,301 (2,4);5,177(4,5);3,539(16 ,0);0,000(3,0)  8,922 (4.0); 8.657 (0.6); 8.655 (0.6); 8.653 (0.5); 8.647 (0.5); 8,645 (0.6); 8,643 (0.6); 7,725 7.721 (0.9), 7.706 (0.6), 7.701 (0.6), 7.621 (0.6), 7.618 (1, 0), 7.616 (0.6), and 7.599 (7.921). 0.7), 7.365 (0.5), 7.362 (0.5), 7.353 (0.5), 7.350 (0.5), 7.346 (0.5), 7.271 (7.4), 5.301 (2 , 4), 5.177 (4.5), 3.539 (16, 0), 0.000 (3.0)
Beispiel No. H1 -36: 1H-NMR (400 MHz, CDC δ, ppm) Example No. H1 -36: 1 H-NMR (400 MHz, CDC δ, ppm)
8,956(4,5);8,856(0,9);8,853(0,9);8,851 (0,8);8,078(0,9);8,074(0,9);7,261 (47,6);5,453(3, 6);3,668(16,0);2,090(1 ,0);1 ,256(0,8);0,921 (0,6);0,008(0,6);0,000(21 ,0);-0,009(0,6) 8.956 (4.5), 8.856 (0.9), 8.853 (0.9), 8.851 (0.8), 8.078 (0.9), 8.074 (0.9), 7.261 (47.6), 5.453 (3, 6); 3.668 (16.0); 2.090 (1, 0); 1, 256 (0.8); 0.921 (0.6); 0.008 (0.6); 0.000 (21, 0); -0.009 (0.6)
Beispiel No. H1 -61 : 1H-NMR (400 MHz, CDCb δ, ppm) Example No. H1 -61: 1 H NMR (400 MHz, CDCb δ, ppm)
8,952(4,5);7,817(0,6);7,814(0,7);7,797(0,8);7,795(0,8);7,783(0,7);7,780(0,7);7,764(0,8) ;7,761 (0,8);7,636(1 ,0);7,632(0,9);7,617(0,7);7,613(0,6);7,590(0,8);7,587(0,8);7,571 (1 ,0 );7,568(1 ,0);7,268(1 1 ,2);5,320(4,0);5,303(2,0);3,543(16,0);0,000(4,3)  8,952 (4.5); 7,817 (0.6); 7,814 (0.7); 7,797 (0.8); 7,795 (0.8); 7,783 (0.7); 7,780 (0.7); 7.764 (0.8); 7.761 (0.8); 7.636 (1.0); 7.632 (0.9); 7.617 (0.7); 7.613 (0.6); 7.590 (0.8); 7.5), 7.571 (1, 0), 7.568 (1, 0), 7.268 (1 1, 2), 5.320 (4.0), 5.303 (2.0), 3.543 (16.0), 0.000 ( 4,3)
Beispiel No. H1 -94: 1H-NMR (400 MHz, CDCb δ, ppm) Example No. H1 -94: 1 H-NMR (400 MHz, CDCb δ, ppm)
8,926(4,3);8,461 (1 ,2);8,455(1 ,2);7,888(0,8);7,882(0,8);7,868(0,9);7,861 (0,8);7,390(1 ,3) ;7,369(1 ,2);7,264(22,9);5,301 (1 ,7);5,046(4,1 );3,475(16,0);1 ,622(0,6);1 ,284(0,6);1 ,256( 0,7);0,000(9,7)  8.926 (4.3), 8.461 (1.2), 8.455 (1.2), 7.888 (0.8), 7.882 (0.8), 7.868 (0.9), 7.861 (0.8), 7.390 (1, 3); 7.369 (1, 2); 7.264 (22.9); 5.301 (1, 7); 5.046 (4.1); 3.475 (16.0); 1.622 (0.6); 1, 284 (0.6); 1, 256 (0.7); 0.000 (9.7)
Beispiel No. H2-1 : 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. H2-1: 1 H-NMR (400 MHz, CDCIs δ, ppm)
8,937(14,9);7,606(2,4);7,602(2,4);7,587(2,7);7,583(2,7);7,463(2,2);7,460(2,4);7,443(3, 3);7,440(3,3);7,371 (1 ,8);7,367(1 ,9);7,352(2,8);7,348(2,6);7,332(2,0);7,328(1 ,8);7,276(2 ,4);7,273(2,6);7,267(35,6);7,257(3,0);7,254(2,9);7,238(1 ,4);7,235(1 ,3);5,377(16,0);5,30 0(5,0);4,326(1 ,1 );4,317(1 ,2);4,305(1 ,6);4,293(1 ,2);4,283(1 ,1 );3,534(0,7);3,527(0,8);3,5 18(0,8);3,512(1 ,9);3,505(1 ,3);3,497(1 ,5);3,490(1 ,4);3,484(1 ,8);3,478(0,7);3,468(0,8);3, 462(0,8);2,338(0,6);2,331 (0,9);2,324(0,9);2,317(1 ,6);2,31 1 (1 ,2);2,303(1 ,5);2,298(1 ,8);2 ,293(1 ,0);2,286(1 ,0);2,276(0,7);2,095(0,6);2,082(1 ,0);2,078(1 ,4);2,070(1 ,3);2,061 (2,2); 2,058(2,1 );2,050(1 ,5);2,044(1 ,2);2,043(1 ,2);0,000(15,9) Beispiel No. H2-3: 1H-NMR (400 MHz, CDCIs δ, ppm) 8,937 (14.9); 7,606 (2.4); 7,602 (2.4); 7,587 (2.7); 7,583 (2.7); 7,463 (2.2); 7,460 (2.4); 7,443 (3, 3); 7,440 (3.3); 7,371 (1, 8); 7,367 (1, 9); 7,352 (2,8); 7,348 (2,6); 7,332 (2,0); 7,328 ( 7,276 (2, 4), 7,273 (2,6), 7,267 (35,6), 7,257 (3,0), 7,254 (2,9), 7,238 (1, 4), 7,235 (1 , 3); 5,377 (16,0); 5,30 0 (5,0); 4,326 (1,1), 4,317 (1,2), 4,305 (1,6), 4,293 (1,2), 4,283 (1, 1); 3.534 (0.7); 3.527 (0.8); 3.518 (0.8); 3.512 (1.9); 3.505 (1.3); 3.497 (1, 5) 3,490 (1,4), 3,484 (1,8), 3,478 (0,7), 3,468 (0,8), 3, 462 (0.8), 2.338 (0.6), 2.331 (0.9), 2.324 (0.9), 2.317 (1.6), 2.31 1 (1.2), 2.303 (1.5 2.298 (1, 8), 2.293 (1, 0), 2.286 (1.0), 2.276 (0.7), 2.095 (0.6), 2.082 (1.0), 2.078 (1, 4), 2.070 (1, 3), 2.061 (2.2); 2.058 (2.1), 2.050 (1.5), 2.044 (1.2), 2.043 (1, 2), 0.000 (15.9) Example no. H2-3: 1 H-NMR (400 MHz, CDCls δ, ppm)
8,895(16,0);7,378(2,0);7,376(1 ,5);7,371 (1 ,0);7,362(1 ,8);7,356(12,4);7,352(3,6);7,349(3 ,7);7,346(13,5);7,339(1 ,8);7,330(1 ,2);7,326(1 ,6);7,324(2,2);7,265(47,0);5,300(4,3);5,1 1 3(13,9);4,248(0,8);4,243(1 ,0);4,234(1 ,2);4,221 (1 ,5);4,209(1 ,3);4,199(1 ,0);3,456(0,7);3, 450(0,7);3,441 (0,7);3,435(1 ,8);3,428(1 ,1 );3,421 (1 ,5);3,413(1 ,2);3,406(1 ,7);3,400(0,7);3 ,391 (0,7);3,385(0,7);2,345(0,5);2,338(0,9);2,331 (0,9);2,324(1 ,5);2,320(1 ,2);2,318(1 ,2); 2,310(1 ,3);2,305(1 ,7);2,299(0,9);2,293(0,9);2,284(0,6);2,055(0,9);2,050(1 ,3);2,045(1 ,2) ;2,042(1 ,2);2,033(1 ,8);2,030(1 ,9);2,022(1 ,4);2,015(1 ,0);2,008(0,7);1 ,259(0,6);0,008(0,5 );0,002(0,7);0,000(19,3);-0,003(1 ,0);-0,009(0,6) Beispiel No. H2-4: 1H-NMR (400 MHz, CDCIs δ, ppm) 8.895 (16.0), 7.378 (2.0), 7.376 (1.5), 7.371 (1, 0), 7.362 (1, 8), 7.356 (12.4), 7.352 (3.6), 7.349 (3,7); 7,346 (13.5); 7,339 (1, 8); 7,330 (1, 2); 7,326 (1,6); 7,324 (2,2); 7,265 (47,0); 5,300 ( 4,3); 5,1 1 3 (13,9); 4,248 (0,8); 4,243 (1, 0); 4,234 (1, 2); 4,221 (1, 5); 4,209 (1, 3) 4.149 (1, 0), 3.456 (0.7), 3, 450 (0.7), 3.441 (0.7), 3.435 (1, 8), 3.442 (1, 1), 3.491 (1, 5) 3,413 (1,2), 3,406 (1, 7), 3,400 (0,7), 3,391 (0,7), 3,385 (0,7), 2,345 (0,5), 2,338 (0, 9); 2,331 (0.9); 2,324 (1,5), 2,320 (1,2), 2,318 (1,2); 2,310 (1,3), 2,305 (1,7), 2,299 (0.9), 2,293 (0.9), 2,284 (0,6), 2,055 (0.9), 2,050 (1,3), 2,045 (1, 2); 2.042 (1, 2); 2.033 (1, 8); 2.030 (1, 9); 2.022 (1, 4); 2.015 (1, 0); 2.008 (0.7); 1, 259 (0.6), 0.008 (0.5), 0.002 (0.7), 0.000 (19.3), - 0.003 (1.0), - 0.009 (0.6) Example no. H2-4: 1 H-NMR (400 MHz, CDCIs δ, ppm)
8,921 (15,1 );7,549(2,0);7,545(4,0);7,539(4,5);7,535(2,4);7,529(2,3);7,525(4,6);7,519(5, 4);7,515(2,2);7,270(23,7);7,218(3,8);7,198(5,1 );7,178(3,0);5,427(15,9);5,301 (16,0);4,3 30(1 ,1 );4,322(1 ,2);4,309(1 ,7);4,297(1 ,4);4,288(1 ,2);3,534(0,7);3,528(0,8);3,519(0,8);3, 513(1 ,8);3,506(1 ,3);3,498(1 ,5);3,491 (1 ,4);3,485(1 ,8);3,479(0,7);3,469(0,8);3,463(0,8);2 ,349(0,6);2,343(0,9);2,335(0,9);2,328(1 ,6);2,323(1 ,3);2,314(1 ,5);2,310(1 ,8);2,297(1 ,0); 2,288(0,7);2,120(0,6);2,107(1 ,0);2,102(1 ,4);2,095(1 ,2);2,085(2,2);2,082(2,2);2,075(1 ,5) ;2,067(1 ,3);2,063(1 ,9);2,045(2,0);1 ,277(0,6);1 ,259(1 ,3);1 ,241 (0,6);0,000(9,5)  8.921 (15.1), 7.549 (2.0), 7.545 (4.0), 7.539 (4.5), 7.535 (2.4), 7.529 (2.3), 7.525 (4.6), 7.519 (5, 4), 7.515 (2.2), 7.270 (23.7), 7.218 (3.8), 7.198 (5.1), 7.178 (3.0), 5.427 (15.9), 5.301 ( 4,309 (1, 7); 4,297 (1, 4); 4,288 (1, 2); 3,534 (0.7); 3.528 (0.8), 3.519 (0.8), 3.513 (1, 8), 3.506 (1.3), 3.498 (1.5), 3.491 (1.4), 3.485 (1, 8) 3.479 (0.7), 3.469 (0.8), 3.463 (0.8), 2.349 (0.6), 2.343 (0.9), 2.355 (0.9), 2.328 (1, 6 2,323 (1,3), 2,314 (1,5), 2,310 (1,8), 2,297 (1,0); 2.288 (0.7); 2.120 (0.6); 2.107 (1, 0); 2.102 (1, 4); 2.095 (1.2); 2.085 (2.2); 2.082 (2.2); 2.075 (1, 5); 2.067 (1, 3); 2.063 (1, 9); 2.045 (2.0); 1, 277 (0.6); 1, 259 (1, 3); 1, 241 (0 0,000 (9.5);, 6)
Beispiel No. H2-1 1 : 1H-NMR (400 MHz, CDCIs δ, ppm) Example No. H2-1 1: 1 H NMR (400 MHz, CDCls δ, ppm)
8,908(16,0);7,506(0,9);7,503(1 ,0);7,488(1 ,8);7,484(2,1 );7,469(1 ,0);7,465(1 ,2);7,423(0, 7);7,419(0,7);7,410(0,8);7,405(1 ,5);7,402(1 ,1 );7,400(1 ,0);7,398(0,9);7,391 (1 ,1 );7,389(1 ,0);7,384(1 ,4);7,379(0,9);7,370(1 ,0);7,366(0,8);7,271 (22,1 );7,139(3,0);7,120(4,8);7,1 18 (4,5);7,102(1 ,4);7,099(1 ,7);7,096(1 ,5);7,094(1 ,0);5,301 (13,2);5,249(8,4);5,247(8,4);4,2 83(0,9);4,279(1 ,0);4,270(1 ,2);4,257(1 ,6);4,245(1 ,3);4,235(1 ,1 );3,528(0,6);3,524(0,6);3, 507(1 ,6);3,501 (1 ,1 );3,493(1 ,4);3,486(1 ,1 );3,480(1 ,5);3,463(0,7);3,458(0,7);2,342(0,5);2 ,335(0,9);2,328(0,9);2,321 (1 ,5);2,315(1 ,2);2,307(1 ,4);2,302(1 ,7);2,297(1 ,0);2,290(1 ,0); 2,281 (0,6);2,106(0,5);2,092(1 ,0);2,088(1 ,3);2,080(1 ,2);2,077(1 ,1 );2,070(1 ,9);2,068(1 ,9) ;2,060(1 ,4);2,052(1 ,1 );2,045(1 ,1 );1 ,259(0,5);0,000(9,1 ) Beispiel No. H2-15: 1H-NMR (400 MHz, CDCIs δ, ppm) 7.908 (16.0), 7.506 (0.9), 7.503 (1, 0), 7.488 (1.8), 7.484 (2.1), 7.469 (1, 0), 7.465 (1, 2), 7.423 (0, 7); 7.419 (0.7); 7.410 (0.8); 7.405 (1, 5); 7.402 (1, 1); 7,400 (1, 0); 7,398 (0.9); 7,391 ( 1, 1), 7.389 (1, 0), 7.384 (1, 4), 7.379 (0.9), 7.370 (1, 0), 7.366 (0.8), 7.271 (22.1), 7.139 (3 7,120 (4,8); 7,118 (4,5); 7,102 (1, 4); 7,099 (1, 7); 7,096 (1, 5); 7,094 (1, 0); 5,301 (13.2); 5.249 (8.4); 5.247 (8.4); 4.2 83 (0.9); 4.279 (1, 0); 4.270 (1, 2); 4.257 (1, 6) 4.245 (1, 3); 4.235 (1, 1); 3.528 (0.6); 3.524 (0.6); 3.507 (1, 6); 3.501 (1, 1); 3.493 (1, 4); 3.486 (1, 1); 3.486 (1, 5); 3.463 (0.7); 3.458 (0.7); 2.342 (0.5); 2.335 (0.9); 2.328 (0); 9), 2,321 (1,5), 2,315 (1,2), 2,307 (1,4), 2,302 (1,7), 2,297 (1,0), 2,290 (1,0); 2.281 (0.6); 2.106 (0.5); 2.092 (1, 0); 2.088 (1, 3); 2.080 (1, 2); 2.077 (1, 1); 2.070 (1, 9); 2.068 (1, 9); 2.060 (1, 4); 2.052 (1, 1); 2.045 (1, 1); 1, 259 (0.5); 0.000 (9.1) Example No. H2-15: 1 H-NMR (400 MHz, CDCIs δ, ppm)
8,893(16,0);7,513(1 ,3);7,497(1 ,6);7,493(2,3);7,477(2,3);7,470(1 ,3);7,454(1 ,2);7,266(45 ,1 );6,899(1 ,3);6,892(1 ,8);6,877(2,8);6,871 (3,8);6,866(1 ,6);6,857(3,0);6,855(3,0);6,850( 3,0);6,845(1 ,5);6,837(1 ,5);6,829(0,8);5,301 (4,1 );5,208(10,8);5,206(10,5);4,256(1 ,5);4,2 48(1 ,7);4,235(2,3);4,222(1 ,8);4,213(1 ,5);3,519(1 ,0);3,514(1 ,0);3,498(2,2);3,492(1 ,7);3, 484(2,0);3,477(1 ,6);3,470(2,1 );3,454(0,9);3,450(0,9);2,352(0,8);2,345(1 ,3);2,338(1 ,3);2 ,331 (2,2);2,317(2,0);2,31 1 (2,3);2,300(1 ,4);2,292(0,9);2,130(0,8);2,1 17(1 ,5);2,1 13(1 ,9); 2,105(1 ,8);2,093(2,7);2,085(2,0);2,077(1 ,5);2,072(1 ,6);1 ,670(1 ,4);1 ,255(1 ,2);0,008(0,6) ;0,000(19,3);-0,009(0,6)  8.893 (16.0), 7.513 (1, 3), 7.497 (1, 6), 7.493 (2.3), 7.477 (2.3), 7.470 (1, 3), 7.454 (1, 2), 7.266 (45, 1); 6.899 (1, 3), 6.892 (1, 8), 6.877 (2.8), 6.871 (3.8), 6.866 (1.6), 6.857 (3.0), 6.855 ( 3.0), 6.850 (3.0), 6.845 (1.5), 6.837 (1.5), 6.829 (0.8), 5.301 (4.1), 5.208 (10.8), 5.206 (10 4,256 (1, 5); 4,248 (1, 7); 4,235 (2,3); 4,222 (1, 8); 4,213 (1, 5); 3,519 (1, 0); 3,514 (1, 0); 3.498 (2.2); 3.492 (1, 7); 3, 484 (2.0); 3.477 (1, 6); 3.470 (2.1); 3.454 (0.9); 3,450 (0.9), 2,352 (0.8), 2,345 (1,3), 2,338 (1,3), 2,331 (2,2), 2,317 (2,0), 2,31 1 (2 , 3); 2,300 (1,4); 2,292 (0,9); 2,130 (0,8); 2,117 (1, 5); 2,113 (1,9); 2.105 (1, 8); 2.093 (2.7); 2.085 (2.0); 2.077 (1, 5); 2.072 (1, 6); 1, 670 (1, 4); 1, 255 (1, 2), 0.008 (0.6), 0.000 (19.3), - 0.009 (0.6)
Beispiel No. H2-21 : 1H-NMR (400 MHz, CDC δ, ppm) Example No. H2-21: 1 H-NMR (400 MHz, CDC δ, ppm)
8,854(14,9);8,607(1 ,8);8,605(2,0);8,603(2,0);8,600(1 ,9);8,595(1 ,9);8,593(2,0);8,591 (2, 0);8,588(1 ,8);7,663(1 ,5);7,658(1 ,5);7,643(3,3);7,639(3,2);7,624(2,2);7,620(2,1 );7,529(2 ,2);7,526(3,7);7,524(2,3);7,510(1 ,7);7,507(2,7);7,504(1 ,6);7,312(2,0);7,309(1 ,9);7,299( 1 ,9);7,296(1 ,9);7,293(1 ,9);7,290(1 ,7);7,280(1 ,9);7,277(1 ,8);7,266(40,9);5,300(1 ,0);5,24 2(16,0);4,235(0,7);4,231 (0,8);4,227(0,9);4,224(0,9);4,217(1 ,2);4,209(1 ,2);4,204(1 ,7);4, 198(1 ,2);4,191 (1 ,4);4,183(0,9);4,180(1 ,0);4,177(0,9);4,173(0,9);3,840(0,8);3,834(0,9);3 ,825(0,8);3,819(1 ,9);3,813(1 ,2);3,810(1 ,0);3,804(1 ,7);3,799(1 ,1 );3,796(1 ,1 );3,790(1 ,7); 3,784(0,8);3,775(0,7);3,769(0,8);2,315(0,9);2,308(1 ,1 );2,301 (1 ,5);2,295(1 ,3);2,287(1 ,5) ;2,281 (1 ,7);2,277(1 ,0);2,270(1 ,0);2,261 (0,7);2,1 17(0,6);2,1 13(1 ,0);2,1 10(1 ,2);2,106(1 ,1 );2,102(1 ,2);2,098(1 ,2);2,092(1 ,7);2,090(1 ,9);2,081 (1 ,4);2,072(1 ,0);2,066(0,7);2,044(0, 6);1 ,692(1 ,8);1 ,259(0,7);1 ,256(0,6);0,008(0,5);0,000(17,4) Beispiel No. H2-36: 1H-NMR (400 MHz, CDC δ, ppm) 8.854 (14.9), 8.607 (1, 8), 8.605 (2.0), 8.603 (2.0), 8.600 (1.9), 8.595 (1.9), 8.593 (2.0), 8.591 (2, 0); 8,588 (1, 8); 7,663 (1, 5); 7,658 (1, 5); 7,643 (3,3); 7,639 (3,2); 7,624 (2,2); 7,620 ( 7.5), 7.529 (2, 2), 7.526 (3.7), 7.524 (2.3), 7.510 (1, 7), 7.507 (2.7), 7.504 (1, 6), 7.312 (2 7, 299 (1, 9); 7,296 (1, 9); 7,296 (1, 9); 7,293 (1, 9); 7,290 (1, 7); 7,280 (1, 9); 7,277 (1, 7); 7,266 (40,9), 5,300 (1, 0), 5,24 2 (16,0), 4,235 (0,7), 4,231 (0,8), 4,227 (0,9), 4,224 ( 4,217 (1,2), 4,209 (1,2), 4,204 (1, 7), 4,198 (1,2), 4,191 (1,4), 4,183 (0,9), 4,180 (1, 0); 4.177 (0.9); 4.173 (0.9); 3.840 (0.8); 3.834 (0.9); 3, 825 (0.8); 3.819 (1, 9); 3.813 (1, 2); 3.810 (1, 0); 3.804 (1, 7); 3.799 (1, 1); 3.796 (1, 1); 3.790 (1, 7); 3.784 (0.8); 3.775 (0.7); 3.769 (0.8); 2.315 (0.9); 2.308 (1, 1); 2.301 (1, 5); 2.295 (1, 3); 2.287 (1, 5), 2.281 (1, 7), 2.277 (1, 0), 2.270 (1, 0), 2.261 (0.7), 2.1 (0.6), 2.1 (1 , 2), 2,10 (1, 2), 2,106 (1,1), 2,102 (1,2), 2,098 (1,2), 2,092 (1, 7), 2,090 (1, 9), 2,081 (1, 4); 2.072 (1, 0); 2.066 (0.7); 2.044 (0, 6); 1, 692 (1, 8); 1, 259 (0.7); 1, 256 (0 , 6); 0.008 (0.5); 0.000 (17.4) Example no. H2-36: 1 H-NMR (400 MHz, CDC δ, ppm)
9,135(0,6);8,921 (16,0);8,803(2,7);8,802(3,0);8,798(2,9);8,797(2,6);7,991 (3,0);7,989(3, 1 );7,986(3,0);7,984(2,8);7,271 (0,5);7,270(0,6);7,2694(0,8);7,2685(1 ,0);7,265(52,9);5,5 34(13,8);5,300(2,5);4,478(0,8);4,473(1 ,0);4,464(1 ,2);4,451 (1 ,6);4,446(1 ,2);4,439(1 ,3);4 ,429(1 ,1 );4,425(0,9);3,844(0,7);3,838(0,7);3,829(0,8);3,823(1 ,8);3,817(1 ,1 );3,809(1 ,6); 3,800(1 ,1 );3,794(1 ,6);3,788(0,7);3,779(0,7);3,773(0,7);2,362(0,5);2,355(0,9);2,348(0,9) ;2,340(1 ,6);2,335(1 ,2);2,327(1 ,4);2,321 (1 ,7);2,316(0,9);2,309(1 ,0);2,301 (0,6);2,076(0,9 );2,070(1 ,3);2,064(1 ,2);2,052(1 ,9);2,044(1 ,5);2,038(1 ,1 );2,036(1 ,1 );2,029(0,7);1 ,952(0, 5);1 ,255(1 ,5);0,008(0,6);0,000(24,2);-0,009(0,7) Beispiel No. H2-61 : 1H-NMR (400 MHz, CDC δ, ppm) 9.135 (0.6), 8.921 (16.0), 8.803 (2.7), 8.802 (3.0), 8.798 (2.9), 8.797 (2.6), 7.991 (3.0), 7.989 (3, 1); 7.986 (3.0); 7.984 (2.8); 7.271 (0.5); 7.270 (0.6); 7.2694 (0.8); 7.2685 (1.0) 7,265 (52.9); 5.5 34 (13.8); 5,300 (2.5); 4,478 (0.8); 4,473 (1, 0); 4,464 (1, 2); 4,451 (1 4,446 (1, 2); 4,439 (1,3); 4,429 (1,1); 4,425 (0,9); 3,844 (0,7); 3,838 (0,7); 3,829 ( 0.8); 3.823 (1, 8); 3.817 (1, 1); 3.809 (1, 6); 3,800 (1, 1), 3,794 (1,6), 3,788 (0,7), 3,779 (0,7), 3,773 (0,7), 2,362 (0,5), 2,355 (0,9), 2,348 (0.9); 2,340 (1,6), 2,335 (1,2), 2,327 (1,4), 2,321 (1,7), 2,316 (0,9), 2,309 (1,0), 2,301 ( 0.6), 2.076 (0.9), 2.070 (1, 3), 2.064 (1.2), 2.052 (1.9), 2.044 (1.5), 2.038 (1, 1), 2.036 (1 , 1); 2.029 (0.7); 1, 952 (0, 5); 1, 255 (1, 5); 0.008 (0.6); 0.000 (24.2); - 0.009 (0.7) Example No. H2-61: 1 H-NMR (400 MHz, CDC δ, ppm)
8,906(1 1 ,8);7,741 (2,9);7,737(2,7);7,723(6,4);7,703(3,5);7,581 (1 ,3);7,578(1 ,5);7,563(3, 5);7,558(3,1 );7,544(2,7);7,539(2,6);7,535(3,1 );7,531 (2,9);7,516(3,4);7,513(3,1 );7,497(1 ,2);7,310(0,5);7,262(106,0);7,212(0,6);6,998(0,6);5,410(16,0);5,300(2,8);4,302(1 ,8);4,2 93(2,0);4,281 (2,8);4,269(2,1 );4,259(1 ,9);3,623(1 ,2);3,602(2,7);3,588(2,4);3,580(2,2);3, 574(2,5);3,559(1 ,3);2,360(1 ,4);2,345(2,7);2,331 (2,5);2,326(2,6);2,315(1 ,6);2,213(1 ,0);2 ,195(2,1 );2,176(3,3);2,169(2,1 );2,160(1 ,7);2,089(0,8);2,045(0,6);1 ,572(7,3);1 ,255(1 ,0); 0,000(43,3);-0,008(2,0)  7.907 (1, 8); 7.741 (2.9); 7.737 (2.7); 7.723 (6.4); 7.703 (3.5); 7.581 (1.3); 7.578 (1, 5); 7,563 (3,5); 7,558 (3,1); 7,544 (2,7); 7,539 (2,6); 7,535 (3,1); 7,531 (2,9); 7,516 (3,4); 7,513 (3.1); 7.497 (1,2); 7,310 (0.5); 7,262 (106,0); 7,212 (0.6); 6,998 (0,6); 5,410 (16,0); 5,300 (5) 4,802 (1,8); 4,293 (2,0); 4,281 (2,8); 4,269 (2,1); 4,259 (1,9); 3,623 (1, 2); 3.602 (2.7); 3.588 (2.4); 3.580 (2.2); 3, 574 (2.5); 3.559 (1.3); 2.356 (1.4); 2.355 (2.7) 2,331 (2,5); 2,326 (2,6); 2,315 (1,6); 2,213 (1,0); 2,195 (2,1); 2,176 (3,3); 2,169 (2,169); 2.160 (1, 7); 2.089 (0.8); 2.045 (0.6); 1, 572 (7.3); 1, 255 (1, 0); 0,000 (43.3) - 0.008 (2.0)
Beispiel No. H2-94: 1H-NMR (400 MHz, CDC δ, ppm) Example No. H2-94: 1 H-NMR (400 MHz, CDC δ, ppm)
8,884(16,0);8,396(3,3);8,395(3,4);8,390(3,4);7,768(2,7);7,762(2,6);7,747(2,9);7,741 (2, 9);7,325(3,9);7,324(3,9);7,305(3,5);7,303(3,3);7,273(0,5);7,272(0,7);7,271 (0,9);7,268(3 4,9);7,265(0,5);5,301 (6,6);5,166(1 1 ,6);4,259(0,9);4,254(1 ,0);4,246(1 ,2);4,233(1 ,6);4,22 8(1 ,2);4,220(1 ,3);4,210(1 ,0);4,207(0,9);3,492(0,7);3,486(0,8);3,477(0,8);3,471 (1 ,8);3,4 65(1 ,2);3,457(1 ,6);3,449(1 ,2);3,442(1 ,7);3,436(0,7);3,428(0,7);3,421 (0,7);2,384(0,5);2, 377(0,9);2,370(0,9);2,363(1 ,5);2,357(1 ,3);2,349(1 ,4);2,343(1 ,7);2,338(0,9);2,332(1 ,0);2 ,323(0,6);2,152(0,5);2,139(1 ,0);2,135(1 ,3);2,127(1 ,2);2,124(1 ,1 );2,1 14(1 ,9);2,107(1 ,4); 2,099(1 ,0);2,092(0,6);1 ,680(1 ,8);1 ,255(0,5);0,000(14,3)  8.884 (16.0); 8,396 (3.3); 8,395 (3.4); 8,390 (3.4); 7.768 (2.7); 7,762 (2.6); 7.747 (2.9) 7.741 (2,9); 7,325 (3,9); 7,324 (3,9); 7,305 (3,5); 7,303 (3,3); 7,273 (0.5); 7,272 (0,7); 7,271 ( 7.29 (3.4.9), 7.268 (0.5), 5.301 (6.6), 5.166 (1, 1, 6), 4.259 (0.9), 4.254 (1, 0), 4.246 (1,2), 4,233 (1,6), 4,22 8 (1,2), 4,220 (1,3), 4,210 (1, 0), 4,207 (0,9), 3,492 (0,7) 3.486 (0.8), 3.477 (0.8), 3.471 (1, 8), 3.465 (1, 2), 3.457 (1, 6), 3.499 (1, 2), 3.442 (1, 7); 3,436 (0,7); 3,428 (0,7); 3,421 (0,7); 2,384 (0,5); 2,337 (0,9); 2,370 (0,9); 2,363 (1 , 5), 2,357 (1,3), 2,349 (1,4), 2,343 (1,7), 2,338 (0,9), 2,332 (1,0), 2, 323 (0,6), 2,152 ( 2,135 (1, 3); 2,127 (1,2); 2,124 (1,1); 2,114 (1,9); 2,107 (1,4); 2.099 (1, 0); 2.092 (0.6); 1, 680 (1, 8); 1, 255 (0.5); 0.000 (14.3)
Weiterer Gegenstand der vorliegenden Erfindung ist die Verwendung mindestens einer erfindungsgemäßen Verbindung, ausgewählt aus der Gruppe, bestehend aus substituierten Heteroarylcarbonsäurehydraziden der allgemeinen Formel (I), sowie von beliebigen Mischungen dieser erfindungsgemäßen substituierten Another object of the present invention is the use of at least one compound of the invention selected from the group consisting of substituted Heteroarylcarbonsäurehydraziden the general formula (I), as well as any mixtures of these substituted according to the invention
Heteroarylcarbonsäurehydrazide der allgemeinen Formel (I) mit weiteren Heteroarylcarbonsäurehydrazide of the general formula (I) with further
agrochemischen Wirkstoffen wie beispielsweise Fungizide, Insektizide, Herbizide, Pflanzenwachstumsregulatoren oder Safener, zur Steigerung der Widerstandsfähigkeit von Pflanzen gegenüber abiotischen Stressfaktoren, bevorzugt Trockenstress, sowie zur Stärkung des Pflanzenwachstums und/oder zur Erhöhung des Pflanzenertrags. agrochemical active substances such as, for example, fungicides, insecticides, herbicides, plant growth regulators or safeners, for increasing the resistance of plants to abiotic stress factors, preferably drought stress, and for strengthening plant growth and / or for increasing the plant yield.
Weiterer Gegenstand der vorliegenden Erfindung ist eine Sprühlösung zur Behandlung von Pflanzen, enthaltend eine zur Steigerung der Widerstandsfähigkeit von Pflanzen gegenüber abiotischen Stressfaktoren wirksame Menge von mindestens einer Verbindung, ausgewählt aus der Gruppe, bestehend aus den erfindungsgemäß substituierten Heteroarylcarbonsäurehydraziden, der allgemeinen Formel (I). Zu den dabei relativierbaren abiotischen Stressbedingungen können zum Beispiel Hitze, Dürre, Kälte- und Trockenstress (Stress verursacht durch Trockenheit und/oder Wassermangel), osmotischer Stress, Staunässe, erhöhter Bodensalzgehalt, erhöhtes Ausgesetztsein an Mineralien, Ozonbedingungen, Starklichtbedingungen, beschränkte Verfügbarkeit von Stickstoffnährstoffen, beschränkte Verfügbarkeit von A further subject of the present invention is a spray solution for the treatment of plants, comprising an amount of at least one effective for increasing the resistance of plants to abiotic stress factors A compound selected from the group consisting of the inventively substituted Heteroarylcarbonsäurehydraziden, the general formula (I). For example, heat, drought, cold and drought stress (stress caused by drought and / or lack of water), osmotic stress, waterlogging, increased soil salt content, increased exposure to minerals, ozone conditions, high light conditions, limited availability of nitrogen nutrients, limited availability of
Phosphornährstoffen zählen. In einer Ausführungsform kann beispielsweise vorgesehen sein, dass die Counting phosphorus nutrients. For example, in one embodiment, it may be provided that the
erfindungsgemäßen Verbindungen, d. h. die entsprechenden erfindungsgemäß substituierten Heteroarylcarbonsäurehydrazide der allgemeinen Formel (I), durch eine Sprühapplikation auf entsprechend zu behandelnde Pflanzen oder Pflanzenteile aufgebracht werden. Die Verwendung der erfindungsgemäßen Verbindungen der allgemeinen Formel (I) oder deren Salze erfolgt vorzugsweise mit einer Dosierung zwischen 0,00005 und 3 kg/ha, besonders bevorzugt zwischen 0,0001 und 2 kg/ha, insbesondere bevorzugt zwischen 0,0005 und 1 kg/ha, im Speziellen bevorzugt zwischen 0,001 und 0,25 kg/ha. Unter der Bezeichnung Resistenz bzw. Widerstandsfähigkeit gegenüber abiotischem Stress werden im Rahmen der vorliegenden Erfindung verschiedenartige Vorteile für Pflanzen verstanden. Solche vorteilhaften Eigenschaften äußern sich beispielsweise in den nachfolgend genannten verbesserten Pflanzencharakteristika: verbessertes Wurzelwachstum hinsichtlich Oberfläche und Tiefe, vermehrte Ausläuferbildung oder Bestückung, stärkere und produktivere Ausläufer und Bestockungstriebe, Compounds of the invention, d. H. the corresponding inventively substituted Heteroarylcarbonsäurehydrazide of the general formula (I), are applied by a spray application to be treated according to plants or plant parts. The use of the compounds of general formula (I) or salts thereof according to the invention is preferably carried out with a dosage between 0.00005 and 3 kg / ha, more preferably between 0.0001 and 2 kg / ha, particularly preferably between 0.0005 and 1 kg / ha, more preferably between 0.001 and 0.25 kg / ha. In the context of the present invention, the term resistance or resistance to abiotic stress is understood to mean various advantages for plants. Such advantageous properties are manifested, for example, in the following improved plant characteristics: improved root growth in terms of surface area and depth, increased tailing or stocking, stronger and more productive shoots and tillers,
Verbesserung des Sprosswachstums, erhöhte Standfestigkeit, vergrößerte Improvement of shoot growth, increased stability, increased
Sprossbasisdurchmesser, vergrößerte Blattfläche, höhere Erträge an Nähr- und Inhaltsstoffen, wie z.B. Kohlenhydrate, Fette, Öle, Proteine, Vitamine, Mineralstoffe, ätherische Öle, Farbstoffe, Fasern, bessere Faserqualität, früheres Blühen, gesteigerte Blütenanzahl, reduzierter Gehalt an toxischen Produkten wie Mycotoxine, reduzierter Gehalt an Rückständen oder unvorteilhaften Bestandteilen jeglicher Art oder bessere Verdaulichkeit, verbesserte Lagerstabilität des Erntegutes, verbesserter Toleranz gegenüber unvorteilhaften Temperaturen, verbesserter Toleranz gegenüber Dürre und Trockenheit, wie auch Sauerstoffmangel durch Wasserüberschuss, verbesserte Toleranz gegenüber erhöhten Salzgehalten in Böden und Wasser, gesteigerte Sprout base diameter, increased leaf area, higher yields of nutrients and ingredients, such as carbohydrates, fats, oils, proteins, vitamins, minerals, essential oils, dyes, fibers, better fiber quality, earlier flowering, increased number of flowers, reduced content of toxic products such as mycotoxins , reduced content of residues or unfavorable ingredients of any kind or better digestibility, improved storage stability of the crop, improved tolerance to unfavorable temperatures, improved tolerance to drought and dryness, as well as oxygen deficiency due to excess water, improved Tolerance to increased salt levels in soils and water, increased
Toleranz gegenüber Ozonstress, verbesserte Verträglichkeit gegenüber Herbiziden und anderen Pflanzenbehandlungsmitteln, verbesserte Wasseraufnahme und Tolerance to ozone stress, improved tolerance to herbicides and other plant treatment agents, improved water absorption and
Photosyntheseleistung, vorteilhafte Pflanzeneigenschaften, wie beispielsweise Beschleunigung der Reifung, gleichmäßigere Abreife, größere Anziehungskraft für Nützlinge, verbesserte Bestäubung oder andere Vorteile, die einem Fachmann durchaus bekannt sind. Photosynthetic performance, beneficial plant properties, such as acceleration of maturation, more uniform maturity, greater attraction for beneficials, improved pollination or other benefits that are well known to a person skilled in the art.
Insbesondere zeigt die Verwendung einer oder mehrerer erfindungsgemäßer In particular, the use of one or more inventive
Verbindungen der allgemeinen Formel (I) in der Sprühapplikation auf Pflanzen und Pflanzenteilen die beschriebenen Vorteile. Die kombinierte Verwendung von erfindungsgemäß substituierten Heteroarylcarbonsäurehydraziden der allgemeinen Formel (I) mit gentechnisch veränderten Sorten in Bezug auf erhöhte abiotische Stresstoleranz ist darüber hinaus ebenfalls möglich. Compounds of general formula (I) in the spray application to plants and parts of plants the advantages described. The combined use of substituted heteroarylcarboxylic according to the invention of the general formula (I) with genetically modified varieties with respect to increased abiotic stress tolerance is also possible.
Die weiter oben genannten verschiedenartigen Vorteile für Pflanzen lassen sich bekannterweise partiell zusammenfassen und mit allgemein gültigen Begriffen belegen. Soche Begriffe sind beispielsweise die nachfolgend aufgeführten The various advantages for plants mentioned above can, as is known, be partially summarized and substantiated by generally valid terms. Soche terms are, for example, those listed below
Bezeichnungen: phytotonischer Effekt, Widerstandsfähigkeit gegenüber Terms: phytotonic effect, resistance to
Stressfaktoren, weniger Pflanzenstress, Pflanzengesundheit, gesunde Pflanzen, Pflanzenfitness, („Plant Fitness"),„Plant Wellness",„Plant Concept",„Vigor Effect", „Stress Shield", Schutzschild,„Crop Health",„Crop Health Properties",„Crop Health Products",„Crop Health Management",„Crop Health Therapy",„Plant Health", Plant Health Properties", Plant Health Products",„Plant Health Management",„Plant Health Therapy", Grünungseffekt („Greening Effect" oder„Re-greening Effect"),„Freshness" oder andere Begriffe, die einem Fachmann durchaus bekannt sind. Stress Factors, Less Plant Stress, Plant Health, Healthy Plants, Plant Fitness, Plant Wellness, Plant Concept, Vigor Effect, Stress Shield, Shield, Crop Health, Crop Health Properties "Crop Health Products", "Crop Health Management", "Crop Health Therapy", "Plant Health", Plant Health Properties, "Plant Health Products", "Plant Health Management", "Plant Health Therapy", Greening Effect (" Greening effect "or" re-greening effect ")," Freshness "or other terms that are well known to a person skilled in the art.
Im Rahmen der vorliegenden Erfindung wird unter einem guten Effekt auf die In the present invention is under a good effect on the
Widerstandsfähigkeit gegenüber abiotischem Stress nicht beschränkend mindestens ein um im Allgemeinen 3 %, insbesondere größer als 5 % besonders bevorzugt größer als 10 % verbessertes Auflaufen, Resistance to abiotic stress not limiting at least one emergence improved by generally 3%, in particular greater than 5%, more preferably greater than 10%,
mindestens einen im Allgemeinen 3 %, insbesondere größer als 5 % besonders bevorzugt größer als 10 % gesteigerten Ertrag, mindestens eine um im Allgemeinen 3 %, insbesondere größer als 5 % besonders bevorzugt größer als 10 % verbesserte Wurzelentwicklung, at least one generally 3%, in particular greater than 5%, particularly preferably greater than 10% increased yield, at least one root development generally improved by 3%, in particular greater than 5%, particularly preferably greater than 10%,
mindestens eine um im Allgemeinen 3 %, insbesondere größer als 5 % besonders bevorzugt größer als 10 % ansteigende Sprossgröße,  at least one shoot size increasing by generally 3%, in particular greater than 5%, particularly preferably greater than 10%,
· mindestens eine um im Allgemeinen 3 %, insbesondere größer als 5 % besonders bevorzugt größer als 10 % vergrößerte Blattfläche, At least one leaf area increased by generally 3%, in particular greater than 5%, particularly preferably greater than 10%,
mindestens eine um im Allgemeinen 3 %, insbesondere größer als 5 % besonders bevorzugt größer als 10 % verbesserte Photosyntheseleistung und/oder mindestens eine um im Allgemeinen 3 %, insbesondere größer als 5 % besonders bevorzugt größer als 10 % verbesserte Blütenausbildung verstanden, wobei die Effekte einzeln oder aber in beliebiger Kombination von zwei oder mehreren Effekten auftreten können. Weiterer Gegenstand der vorliegenden Erfindung ist eine Sprühlösung zur Behandlung von Pflanzen, enthaltend eine zur Steigerung der Widerstandsfähigkeit von Pflanzen gegenüber abiotischen Stressfaktoren wirksame Menge von mindestens einer  at least one generally improved by 3%, in particular greater than 5%, more preferably greater than 10% improved photosynthesis and / or at least one generally improved by 3%, in particular greater than 5%, more preferably greater than 10% improved flower formation, the effects individually or in any combination of two or more effects. A further subject of the present invention is a spray solution for the treatment of plants, comprising an amount of at least one effective for increasing the resistance of plants to abiotic stress factors
Verbindung aus der Gruppe der erfindungsgemäß substituierten Compound from the group of substituted according to the invention
Heteroarylcarbonsäurehydrazide der allgemeinen Formel (I). Die Sprühlösung kann andere übliche Bestandteile aufweisen, wie Lösungsmittel, Formulierhilfsstoffe, insbesondere Wasser, enthalten. Weitere Bestandteile können unter anderem agrochemische Wirkstoffe sein, welche unten noch weiter beschrieben werden. Heteroarylcarbonsäurehydrazide of the general formula (I). The spray solution may comprise other conventional ingredients, such as solvents, formulation auxiliaries, especially water. Other ingredients may include agrochemical agents, which are further described below.
Weiterer Gegenstand der vorliegenden Erfindung ist die Verwendung von Another object of the present invention is the use of
entsprechenden Sprühlösungen zur Steigerung der Widerstandsfähigkeit von Pflanzen gegenüber abiotischen Stressfaktoren. Die nachfolgenden Ausführungen gelten sowohl für die Verwendung einer oder mehrerer erfindungsgemäßer Verbindungen der allgemeinen Formel (I) an sich als auch für die entsprechenden Sprühlösungen. Erfindunsgemäß wurde darüber hinaus gefunden, dass die Anwendung einer oder mehrerer erfindungsgemäßer Verbindungen der allgemeinen Formel (I) in Kombination mit mindestens einem Düngemittel wie weiter unten stehend definiert auf Pflanzen oder in deren Umgebung möglich ist. Düngemittel, die erfindungsgemäß zusammen mit den oben näher erläuterten erfindungsgemäßen Verbindungen der allgemeinen Formel (I) verwendet werden können, sind im Allgemeinen organische und anorganische Stickstoff-haltige corresponding spray solutions to increase the resistance of plants to abiotic stress factors. The following statements apply both to the use of one or more compounds of the general formula (I) according to the invention per se and to the corresponding spray solutions. According to the invention, moreover, it has been found that the use of one or more compounds of the general formula (I) according to the invention in combination with at least one fertilizer, as defined below, is possible on plants or in their environment. Fertilizers which, according to the invention, can be used together with the compounds of the general formula (I) according to the invention which are explained in more detail above, are generally organic and inorganic nitrogen-containing
Verbindungen wie beispielsweise Harnstoffe, Harnstoff-Formaldehyd- Kondensationsprodukte, Aminosäuren, Ammoniumsalze und -nitrate, Kaliumsalze (bevorzugt Chloride, Sulfate, Nitrate), Phosphorsäuresalze und/oder Salze von Compounds such as ureas, urea-formaldehyde condensation products, amino acids, ammonium salts and nitrates, potassium salts (preferably chlorides, sulfates, nitrates), phosphoric acid salts and / or salts of
Phosphoriger Säure (bevorzugt Kaliumsalze und Ammoniumsalze). Insbesondere zu nennen sind in diesem Zusammenhang die NPK-Dünger, d.h. Düngemittel, die Phosphoric acid (preferably potassium salts and ammonium salts). Particularly noteworthy in this connection are the NPK fertilizers, i. Fertilizers that
Stickstoff, Phosphor und Kalium enthalten, Kalkammonsalpeter, d.h. Düngemittel, die noch Calcium enthalten, Ammonsulfatsalpeter (Allgemeine Formel (NH4)2SO4 Ammonium nitrate, ie fertilizers which still contain calcium, ammonium sulfate nitrate (general formula (NH 4 ) 2SO 4)
NH4NO3), Ammonphosphat und Ammonsulfat. Diese Düngemittel sind dem Fachmann allgemein bekannt, siehe auch beispielsweise Ullmann's Encyclopedia of Industrial Chemistry, 5. Edition, Vol. A 10, Seiten 323 bis 431 , Verlagsgesellschaft, Weinheim, 1987. NH 4 NO 3), ammonium phosphate and ammonium sulfate. These fertilizers are well known to those skilled in the art, see also, for example, Ullmann's Encyclopedia of Industrial Chemistry, 5th Edition, Vol. A 10, pages 323 to 431, Verlagsgesellschaft, Weinheim, 1987.
Die Düngemittel können auch Salze aus Mikronährstoffen (bevorzugt Calcium, The fertilizers may also contain salts of micronutrients (preferably calcium,
Schwefel, Bor, Mangan, Magnesium, Eisen, Bor, Kupfer, Zink, Molybdän und Kobalt) und Phytohormonen (z. B. Vitamin B1 und Indol-(lll)essigsäure) oder Gemische davon enthalten. Erfindungsgemäß eingesetzte Düngemittel können auch weitere Salze wie Monoammoniumphosphat (MAP), Diammoniumphosphat (DAP), Kaliumsulfat, Sulfur, boron, manganese, magnesium, iron, boron, copper, zinc, molybdenum and cobalt) and phytohormones (eg, vitamin B1 and indole (III) acetic acid) or mixtures thereof. Fertilizers used according to the invention may also contain other salts such as monoammonium phosphate (MAP), diammonium phosphate (DAP), potassium sulfate,
Kaliumchlorid, Magnesiumsulfat enthalten. Geeignete Mengen für die sekundären Nährstoffe oder Spurenelemente sind Mengen von 0,5 bis 5 Gew.-%, bezogen auf das gesamte Düngemittel. Weitere mögliche Inhaltsstoffe sind Pflanzenschutzmittel, wie beispielsweise Fungizide, Insektizide, Herbizide, Pflanzenwachstumsregulatoren oder Safener, oder Gemische davon. Hierzu folgen weiter unten weitergehende Containing potassium chloride, magnesium sulfate. Suitable amounts for the secondary nutrients or trace elements are amounts of 0.5 to 5 wt .-%, based on the total fertilizer. Further possible ingredients are crop protection agents, such as, for example, fungicides, insecticides, herbicides, plant growth regulators or safeners, or mixtures thereof. Further below follow this
Ausführungen. Versions.
Die Düngemittel können beispielsweise in Form von Pulvern, Granulaten, Prills oder Kompaktaten eingesetzt werden. Die Düngemittel können jedoch auch in flüssiger Form, gelöst in einem wässrigen Medium, eingesetzt werden. In diesem Fall kann auch verdünnter wässriger Ammoniak als Stickstoffdüngemittel eingesetzt werden. Weitere mögliche Inhaltsstoffe für Düngemittel sind beispielsweise in Ullmann's The fertilizers can be used, for example, in the form of powders, granules, prills or compactates. However, the fertilizers can also be used in liquid form dissolved in an aqueous medium. In this case, dilute aqueous ammonia can be used as nitrogen fertilizer. Further possible ingredients for fertilizers are, for example, in Ullmann's
Encyclopedia of Industrial Chemistry, 5. Auflage, 1987, Band A 10, Seiten 363 bis 401 , DE-A 41 28 828, DE-A 19 05 834 und DE-A 196 31 764 beschrieben. Die allgemeine Zusammensetzung der Düngemittel, bei welchen es sich im Rahmen der vorliegenden Erfindung um Einzelnährstoff- und/oder Mehrnährstoffdünger handeln kann, Encyclopedia of Industrial Chemistry, 5th edition, 1987, Volume A 10, pages 363 to 401, DE-A 41 28 828, DE-A 19 05 834 and DE-A 196 31 764 described. The general Composition of the fertilizers, which in the context of the present invention may be single-nutrient and / or complex nutrient fertilizers,
beispielsweise aus Stickstoff, Kalium oder Phosphor, kann innerhalb eines breiten Bereichs variieren. Im Allgemeinen ist ein Gehalt von 1 bis 30 Gew.-% Stickstoff (bevorzugt 5 bis 20 Gew.-%), von 1 bis 20 Gew.-% Kalium (bevorzugt 3 bis 15 Gew.- %) und ein Gehalt von 1 bis 20 Gew.-% Phosphor (bevorzugt 3 bis 10 Gew.-%) vorteilhaft. Der Gehalt von Mikroelementen ist üblicherweise im ppm-Bereich, bevorzugt im Bereich von von 1 bis 1000 ppm. Im Rahmen der vorliegenden Erfindung können das Düngemittel sowie eine oder mehrere erfindungsgemäße Verbindungen der allgemeinen Formel (I) zeitgleich verabreicht werden. Es ist jedoch auch möglich, zunächst das Düngemittel und dann eine oder mehrere erfindungsgemäße Verbindungen der allgemeinen Formel (I) oder zunächst eine oder mehrere Verbindungen der allgemeinen Formel (I) und dann das Düngemittel anzuwenden. Bei nicht zeitgleicher Anwendung einer oder mehrerer erfindungsgemäßer Verbindungen der allgemeinen Formel (I) und des Düngemittels erfolgt im Rahmen der vorliegenden Erfindung jedoch die Anwendung in funktionellem Zusammenhang, insbesondere innerhalb eines Zeitraums von im Allgemeinen 24 Stunden, bevorzugt 18 Stunden, besonders bevorzugt 12 Stunden, speziell 6 Stunden, noch spezieller 4 Stunden, noch weiter spezieller innerhalb 2 Stunden. In ganz besonderen Ausführungsformen der vorliegenden Erfindung erfolgt die Anwendung einer oder mehrerer erfindungsgemäßer Verbindungen der Formel (I) und des For example, nitrogen, potassium or phosphorus may vary within a wide range. In general, a content of 1 to 30 wt .-% of nitrogen (preferably 5 to 20 wt .-%), from 1 to 20 wt .-% potassium (preferably 3 to 15% by weight) and a content of 1 to 20% by weight of phosphorus (preferably 3 to 10% by weight) is advantageous. The content of microelements is usually in the ppm range, preferably in the range of from 1 to 1000 ppm. In the context of the present invention, the fertilizer and one or more compounds of the general formula (I) according to the invention can be administered at the same time. However, it is also possible first to apply the fertilizer and then one or more compounds of the general formula (I) according to the invention or first of all one or more compounds of the general formula (I) and then the fertilizer. In the case of non-simultaneous application of one or more compounds of the general formula (I) and the fertilizer according to the invention, however, the application takes place in a functional context, in particular within a period of generally 24 hours, preferably 18 hours, particularly preferably 12 hours, specifically 6 hours, more specifically 4 hours, even more specifically within 2 hours. In very particular embodiments of the present invention, the use of one or more compounds according to the invention of the formula (I) and of the
Düngemittels in einem zeitlichen Rahmen von weniger als 1 Stunden, vorzugsweise weniger als 30 Minuten, besonders bevorzugt weniger als 15 Minuten. Fertilizer in a time frame of less than 1 hour, preferably less than 30 minutes, more preferably less than 15 minutes.
Bevorzugt ist die Verwendung erfindungsgemäßer Verbindungen der allgemeinen Formel (I) auf Pflanzen aus der Gruppe der Nutzpflanzen, Zierpflanzen, Rasenarten, allgemein genutzte Bäume, die in öffentlichen und privaten Bereichen als Zierpflanzen Verwendungen finden, und Forstbestand. Der Forstbestand umfasst Bäume für die Herstellung von Holz, Zellstoff, Papier und Produkten die aus Teilen der Bäume hergestellt werden. Der Begriff Nutzpflanzen, wie hier verwendet, bezeichnet Preference is given to the use of compounds of the general formula (I) according to the invention on plants from the group of crops, ornamental plants, lawn species, generally used trees which are used as ornamental plants in public and private sectors, and forest stands. The forest stock includes trees for the production of wood, pulp, paper and products made from parts of the trees. The term crops as used herein refers to
Kulturpflanzen, die als Pflanzen für die Gewinnung von Nahrungsmitteln, Futtermitteln, Treibstoffe oder für technische Zwecke eingesetzt werden. Zu den Nutzpflanzen zählen z. B. folgende Pflanzenarten: Triticale, Durum (Hartweizen), Turf, Reben, Getreide, beispielsweise Weizen, Gerste, Roggen, Hafer, Reis, Mais und Hirse; Rüben, beispielsweise Zuckerrüben und Futterrüben; Früchte, beispielsweise Kernobst, Steinobst und Beerenobst, beispielsweise Äpfel, Birnen, Pflaumen, Pfirsiche, Mandeln, Kirschen und Beeren, z. B. Erdbeeren, Himbeeren, Brombeeren; Hülsenfrüchte, beispielsweise Bohnen, Linsen, Erbsen und Sojabohnen; Ölkulturen, beispielsweise Raps, Senf, Mohn, Oliven, Sonnenblumen, Kokos, Crop plants used as plants for the production of food, feed, fuel or for technical purposes. Among the useful plants include z. The following plant species: triticale, durum (durum wheat), turf, vines, cereals, for example wheat, barley, rye, oats, rice, corn and millet; Beets, for example sugar beets and fodder beets; Fruits, such as pome fruit, stone fruit and soft fruit, such as apples, pears, plums, peaches, almonds, cherries and berries, eg. Strawberries, raspberries, blackberries; Legumes, such as beans, lentils, peas and soybeans; Oil crops, such as oilseed rape, mustard, poppy, olives, sunflowers, coconut,
Castorölpflanzen, Kakaobohnen und Erdnüsse; Gurkengewächse, beispielsweise Kürbis, Gurken und Melonen; Fasergewächse, beispielsweise Baumwolle, Flachs, Hanf und Jute; Citrusfrüchte, beispielsweise Orangen, Zitronen, Pampelmusen und Mandarinen; Gemüsesorten, beispielsweise Spinat, (Kopf)-Salat, Spargel, Kohlarten, Möhren, Zwiebeln, Tomaten, Kartoffeln und Paprika; Lorbeergewächse, beispielsweise Avocado, Cinnamomum, Kampfer, oder ebenso Pflanzen wie Tabak, Nüsse, Kaffee, Aubergine, Zuckerrohr, Tee, Pfeffer, Weinreben, Hopfen, Bananen, Castor oil plants, cocoa beans and peanuts; Cucurbits, for example squash, cucumbers and melons; Fiber plants, for example cotton, flax, hemp and jute; Citrus fruits, such as oranges, lemons, grapefruit and mandarins; Vegetables such as spinach, (head) salad, asparagus, cabbages, carrots, onions, tomatoes, potatoes and peppers; Laurel family, such as avocado, cinnamomum, camphor, or plants such as tobacco, nuts, coffee, eggplant, sugar cane, tea, pepper, vines, hops, bananas,
Naturkautschukgewächse sowie Zierpflanzen, beispielsweise Blumen, Sträucher,Natural rubber plants and ornamental plants, such as flowers, shrubs,
Laubbäume und Nadelbäume wie Koniferen. Diese Aufzählung stellt keine Limitierung dar. Deciduous trees and conifers like conifers. This list is not a limitation.
Als besonders geeignete Zielkulturen für die Anwendung des erfindungsgemäßen Verfahrens sind folgende Pflanzen anzusehen: Hafer, Roggen, Triticale, Durum,Particularly suitable target crops for the application of the method according to the invention are the following plants: oats, rye, triticale, durum,
Baumwolle, Aubergine, Turf, Kernobst, Steinobst, Beerenobst, Mais, Weizen, Gerste, Gurke, Tabak, Reben, Reis, Getreide, Birne, Pfeffer, Bohnen, Sojabohnen, Raps, Tomate, Paprika, Melonen, Kohl, Kartoffel und Apfel. Als Bäume, die entsprechend dem erfindungsgemäßen Verfahren verbessert werden können, seien beispielhaft genannt: Abies sp., Eucalyptus sp., Picea sp., Pinus sp., Aesculus sp., Platanus sp., Tilia sp., Acer sp., Tsuga sp., Fraxinus sp., Sorbus sp., Betula sp., Crataegus sp., Ulmus sp., Quercus sp., Fagus sp., Salix sp., Populus sp.. Als bevorzugte Bäume, die entsprechend dem erfindungsgemäßen Verfahren verbessert werden können, können genannt werden: Aus der Baumart Aesculus: A. hippocastanum, A. pariflora, A. carnea; aus der Baumart Platanus: P. aceriflora, P. occidentalis, P. racemosa; aus der Baumart Picea: P. abies; aus der Baumart Pinus: P. radiate, P. ponderosa, P. contorta, P. sylvestre, P. elliottii, P. montecola, P. albicaulis, P. resinosa, P. palustris, P. taeda, P. flexilis, P. jeffregi, P. baksiana, P. strobes; aus der Baumart Eucalyptus: E. grandis, E. globulus, E. camadentis, E. Cotton, aubergine, turf, pome fruit, stone fruit, soft fruit, corn, wheat, barley, cucumber, tobacco, vines, rice, cereals, pear, pepper, beans, soybeans, rapeseed, tomato, peppers, melons, cabbage, potato and apple. Examples of trees which can be improved according to the method of the invention are: Abies sp., Eucalyptus sp., Picea sp., Pinus sp., Aesculus sp., Platanus sp., Tilia sp., Acer sp., Tsuga sp , Fraxinus sp., Sorbus sp., Betula sp., Crataegus sp., Ulmus sp., Quercus sp., Fagus sp., Salix sp., Populus sp .. As preferred trees that can be improved according to the method of the invention , may be mentioned: From the tree species Aesculus: A. hippocastanum, A. pariflora, A. carnea; from the tree species Platanus: P. aceriflora, P. occidentalis, P. racemosa; from the tree species Picea: P. abies; from the tree Pinus: P. radiate, P. ponderosa, P. contorta, P. sylvestre, P. elliottii, P. montecola, P. albicaulis, P. resinosa, P. palustris, P. taeda, P. flexilis, P. jeffregi, P. baksiana, P. strobes; from the tree species Eucalyptus: E. grandis, E. globulus, E. camadentis, E.
nitens, E. obliqua, E. regnans, E. pilularus. Als besonders bevorzugte Bäume, die entsprechend dem erfindungsgemäßen nitens, E. obliqua, E. regnans, E. pilularus. As particularly preferred trees, according to the invention
Verfahren verbessert werden können, können genannt werden: Aus der Baumart Pinus: P. radiate, P. ponderosa, P. contorta, P. sylvestre, P. strobes; aus der Baumart Eucalyptus: E. grandis, E. globulus und E. camadentis. Als besonders bevorzugte Bäume, die entsprechend dem erfindungsgemäßen Methods can be improved can be mentioned: From the tree species Pinus: P. radiate, P. ponderosa, P. contorta, P. sylvestre, P. strobes; from the tree species Eucalyptus: E. grandis, E. globulus and E. camadentis. As particularly preferred trees, according to the invention
Verfahren verbessert werden können, können genannt werden: Rosskastanie, Procedures can be improved: horse chestnut,
Platanengewächs, Linde und Ahornbaum. Sycamore plant, linden and maple tree.
Die vorliegende Erfindung kann auch an beliebigen Rasenarten („turfgrasses") durchgeführt werden, einschließlich„cool season turfgrasses" und„warm season turfgrasses". Beispiele für Rasenarten für die kalte Jahreszeit sind Blaugräser („blue grasses"; Poa spp.), wie„Kentucky bluegrass" (Poa pratensis L),„rough bluegrass" (Poa trivialis L),„Canada bluegrass" (Poa compressa L),„annual bluegrass" (Poa annua L),„upland bluegrass" (Poa glaucantha Gaudin),„wood bluegrass" (Poa nemoralis L.) und„bulbous bluegrass" (Poa bulbosa L); Straussgräser („Bentgrass", Agrostis spp.), wie„creeping bentgrass" (Agrostis palustris Huds.),„colonial bentgrass" (Agrostis tenuis Sibth.),„velvet bentgrass" (Agrostis canina L),„South German Mixed Bentgrass" (Agrostis spp. einschließlich Agrostis tenius Sibth., Agrostis canina L, und Agrostis palustris Huds.), und„redtop" (Agrostis alba L); The present invention may also be practiced on any turfgrasses, including "cool season turfgrasses" and "warm season turfgrasses." Examples of cold season turf species are blue grasses (Poa spp.), Such as "Kentucky bluegrass" (Poa pratensis L), "rough bluegrass" (Poa trivialis L), "Canada bluegrass" (Poa compressa L), "annual bluegrass" (Poa annua L), "upland bluegrass" (Poa glaucantha Gaudin), "Wood bluegrass" (Poa nemoralis L.) and "bulbous bluegrass" (Poa bulbosa L); ostrich grasses ("Bentgrass", Agrostis spp.), Such as "creeping bentgrass" (Agrostis palustris Huds.), "Colonial bentgrass" (Agrostis Tenuis Sibth.), "velvet bentgrass" (Agrostis canina L), "South German Mixed Bentgrass" (Agrostis spp., including Agrostis tenius Sibth., Agrostis canina L, and Agrostis palustris Huds.), and "redtop" (Agrostis alba L );
Schwingel („Fescues", Festucu spp.), wie„red fescue" (Festuca rubra L. spp. rubra), „creeping fescue" (Festuca rubra L),„chewings fescue" (Festuca rubra commutata Gaud.),„sheep fescue" (Festuca ovina L),„hard fescue" (Festuca longifolia Thuill.), „hair fescue" (Festucu capillata Lam.),„tall fescue" (Festuca arundinacea Schreb.) und „meadow fescue" (Festuca elanor L.); Fescue ("Fescues", Festucu spp.), Such as "red fescue" (Festuca rubra L. spp. Rubra), "creeping fescue" (Festuca rubra L), "chewings fescue" (Festuca rubra commutata Gaud.), "Sheep fescue "(Festuca ovina L)," hard fescue "(Festuca longifolia Thuill.)," hair fescue "(Festucu capillata Lam.)," tall fescue "(Festuca arundinacea Schreb.) and" meadow fescue "(Festuca elanor L. );
Lolch („ryegrasses", Lolium spp.), wie„annual ryegrass" (Lolium multiflorum Lam.), „perennial ryegrass" (Lolium perenne L.) und„italian ryegrass" (Lolium multiflorum Lam.); und Weizengräser ("wheatgrasses", Agropyron spp..), wie "fairway wheatgrass" (Agropyron cristatum (L.) Gaertn.),„crested wheatgrass" (Agropyron desertorum (Fisch.) Schult.) und "western wheatgrass" (Agropyron smithii Rydb.). Lolium ("ryegrasses", Lolium spp.), Such as "annual ryegrass" (Lolium multiflorum Lam.), "Perennial ryegrass" (Lolium perenne L.) and "Italian ryegrass" (Lolium multiflorum Lam.); and wheat grasses ("wheatgrasses", Agropyron spp.), such as "fairway wheatgrass" (Agropyron cristatum (L.) Gaertn.), "crested wheatgrass" (Agropyron desertorum (fish.) Schult.) and "western wheatgrass" (Agropyron smithii Rydb.).
Beispiele für weitere "cool season turfgrasses" sind "beachgrass" (Ammophila breviligulata Fern.), "smooth bromegrass" (Bromus inermis Leyss.), Schilf ("cattails") wie "Timothy" (Phleum pratense L), "sand cattail" (Phleum subulatum L), Examples of other "cool season turfgrasses" are "beachgrass" (Ammophila breviligulata Fern.), "Smooth bromegrass" (Bromus inermis leyss.), Reeds ("cattails") such as "Timothy" (Phleum pratense L), "sand cattail" (Phleum subulatum L),
"orchardgrass" (Dactylis glomerata L.), "weeping alkaligrass" (Puccinellia distans (L.) Pari.) und "crested dog's-tail" (Cynosurus cristatus L). "orchardgrass" (Dactylis glomerata L.), "weeping alkaligrass" (Puccinellia distans (L.) Pari.) and "crested dog's-tail" (Cynosurus cristatus L).
Beispiele für "warm season turfgrasses" sind„Bermudagrass" (Cynodon spp. L. C. Rieh), "zoysiagrass" (Zoysia spp. Willd.),„St. Augustine grass" (Stenotaphrum secundatum Walt Kuntze),„centipedegrass" (Eremochloa ophiuroides Munro Hack.), „carpetgrass" (Axonopus affinis Chase),„Bahia grass" (Paspalum notatum Flügge), „Kikuyugrass" (Pennisetum clandestinum Höchst, ex Chiov.),„buffalo grass" (Buchloe daetyloids (Nutt.) Engelm.), "Blue gramma" (Bouteloua gracilis (H.B.K.) Lag. ex Griffiths),„seashore paspalum" (Paspalum vaginatum Swartz) und„sideoats grama" (Bouteloua curtipendula (Michx. Torr.). "Cool season turfgrasses" sind für die erfindungsgemäße Verwendung im Allgemeinen bevorzugt. Besonders bevorzugt sind Blaugras, Straussgras und„redtop", Schwingel und Lolch. Straussgras ist Examples of "warm season turfgrasses" are "Bermudagrass" (Cynodon spp., LC Rieh), "zoysiagrass" (Zoysia spp. Willd.), "St. Augustine grass" (Stenotaphrum secundatum Walt Kuntze), "centipedegrass" (Eremochloa ophiuroides Munro Hack.), "Carpetgrass" (Axonopus affinis chase), "Bahia grass" (Paspalum notatum flügge), "Kikuyugrass" (Pennisetum clandestinum Höchst, ex Chiov.), "Buffalo grass" (Buchloe daetyloids (Nutt.) Engelm.) , "Blue gramma" (Bouteloua gracilis (HBK) lag. Ex Griffiths), "seashore paspalum" (Paspalum vaginatum Swartz) and "sideoats grama" (Bouteloua curtipendula (Michx. Torr.). "Cool season turfgrasses" are for the present invention Use is generally preferred Bleach grass, ostrich grass and "redtop", fescue and lolk are particularly preferred
insbesondere bevorzugt. especially preferred.
Besonders bevorzugt werden mit den erfindungsgemäßen Verbindungen der allgemeinen Formel (I) Pflanzen der jeweils handelsüblichen oder in Gebrauch befindlichen Pflanzensorten behandelt. Unter Pflanzensorten versteht man Pflanzen mit neuen Eigenschaften ("Traits"), die sowohl durch konventionelle Züchtung, durch Mutagenese oder mit Hilfe rekombinanter DNA-Techniken, gezüchtet worden sind. Kulturpflanzen können demnach Pflanzen sein, die durch konventionelle Züchtungs- und Optimierungsmethoden oder durch biotechnologische und gentechnologische Methoden oder Kombinationen dieser Methoden erhalten werden können, einschließlich der transgenen Pflanzen und einschließlich der durch Sortenschutzrechte schützbaren oder nicht schützbaren Pflanzensorten. Das erfindungsgemäße Behandlungsverfahren kann somit auch für die Behandlung von genetisch modifizierten Organismen (GMOs), z. B. Pflanzen oder Samen, verwendet werden. Genetisch modifizierte Pflanzen (oder transgene Pflanzen) sind Pflanzen, bei denen ein heterologes Gen stabil in das Genom integriert worden ist. Der Begriff "heterologes Gen" bedeutet im wesentlichen ein Gen, das außerhalb der Pflanze bereitgestellt oder assembliert wird und das bei Einführung in das Particular preference is given to treating the compounds of the general formula (I) according to the invention with plants of the respective commercially available or used plant cultivars. Plant varieties are understood to be plants with new traits which have been bred either by conventional breeding, by mutagenesis or by recombinant DNA techniques. Crop plants can therefore be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties protectable or non-protectable plant varieties. The treatment method according to the invention can thus also for the treatment of genetically modified organisms (GMOs), z. As plants or seeds are used. Genetically modified plants (or transgenic plants) are plants in which a heterologous gene has been stably integrated into the genome. The term "heterologous gene" essentially means a gene that is provided or assembled outside the plant and that when introduced into the plant
Zellkerngenom, das Chloroplastengenom oder das Hypochondriengenom der transformierten Pflanze dadurch neue oder verbesserte agronomische oder sonstige Eigenschaften verleiht, dass es ein interessierendes Protein oder Polypeptid exprimiert oder dasses ein anderes Gen, das in der Pflanze vorliegt bzw. andere Gene, die in der Pflanze vorliegen, herunterreguliert oder abschaltet (zum Beispiel mittels Antisense- Technologie, Co-suppressionstechnologie oder RNAi-Technologie [RNA Interference]). Ein heterologes Gen, das im Genom vorliegt, wird ebenfalls als Transgen bezeichnet. Ein Transgen, das durch sein spezifisches Vorliegen im Pflanzengenom definiert ist, wird als Transformations- bzw. transgenes Event bezeichnet. Cell nucleus genome, the chloroplast genome or the hypochondrial genome of the transformed plant by conferring new or improved agronomic or other properties by expressing a protein or polypeptide of interest or by having another gene present in the plant or other genes present in the plant; downregulated or switched off (for example by means of antisense technology, co-suppression technology or RNAi technology [RNA Interference]). A heterologous gene present in the genome is also referred to as a transgene. A transgene defined by its specific presence in the plant genome is referred to as a transformation or transgenic event.
Zu Pflanzen und Pflanzensorten, die vorzugsweise mit den erfindungsgemäßen To plants and plant varieties, preferably with the inventive
Verbindungen der allgemeinen Formel (I) behandelt werden, zählen alle Pflanzen, die über Erbgut verfügen, das diesen Pflanzen besonders vorteilhafte, nützliche Merkmale verleiht (egal, ob dies durch Züchtung und/oder Biotechnologie erzielt wurde). Compounds of general formula (I) include all plants which have genetic material conferring on these plants particularly advantageous, useful characteristics (whether obtained by breeding and / or biotechnology).
Pflanzen und Pflanzensorten, die ebenfalls mit den erfindungsgemäßen Verbindungen der allgemeinen Formel (I) behandelt werden können, sind solche Pflanzen, die gegen einen oder mehrere abiotische Stressfaktoren resistent sind. Zu den abiotischen Stressbedingungen können zum Beispiel Hitze, Dürre, Kälte- und Trockenstress,, osmotischer Stress, Staunässe, erhöhter Bodensalzgehalt, erhöhtes Ausgesetztsein an Mineralien, Ozonbedingungen, Starklichtbedingungen, beschränkte Verfügbarkeit von Stickstoffnährstoffen, beschränkte Verfügbarkeit von Phosphornährstoffen oder Vermeidung von Schatten zählen. Plants and plant varieties which can also be treated with the compounds of the general formula (I) according to the invention are those plants which are resistant to one or more abiotic stress factors. Abiotic stress conditions may include, for example, heat, drought, cold and dry stress, osmotic stress, waterlogging, increased soil salinity, increased exposure to minerals, ozone conditions, high light conditions, limited availability of nitrogen nutrients, limited availability of phosphorous nutrients, or avoidance of shade.
Pflanzen und Pflanzensorten, die ebenfalls mit den erfindungsgemäßen Verbindungen der allgemeinen Formel (I) behandelt werden können, sind solche Pflanzen, die durch erhöhte Ertragseigenschaften gekennzeichnet sind. Ein erhöhter Ertrag kann bei diesen Pflanzen z. B. auf verbesserter Pflanzenphysiologie, verbessertem Pflanzenwuchs und verbesserter Pflanzenentwicklung, wie Plants and plant varieties which can also be treated with the compounds of the general formula (I) according to the invention are those plants which are characterized by increased yield properties. An increased yield can in these plants z. B. on improved plant physiology, improved Plant growth and improved plant development, such as
Wasserverwertungseffizienz, Wasserhalteeffizienz, verbesserter Stickstoffverwertung, erhöhter Kohlenstoffassimilation, verbesserter Photosynthese, verstärkter Keimkraft und beschleunigter Abreife beruhen. Der Ertrag kann weiterhin durch eine verbesserte Pflanzenarchitektur (unter Stress- und nicht-Stress-Bedingungen) beeinflusst werden, darunter frühe Blüte, Kontrolle der Blüte für die Produktion von Hybridsaatgut,  Water utilization efficiency, water retention efficiency, improved nitrogen utilization, increased carbon assimilation, improved photosynthesis, increased germination power and accelerated Abreife based. The yield may be further influenced by improved plant architecture (under stress and non-stress conditions), including early flowering, control of flowering for the production of hybrid seed,
Keimpflanzenwüchsigkeit, Pflanzengröße, Internodienzahl und -abstand, Seedling vigor, plant size, internode count and distance,
Wurzelwachstum, Samengröße, Fruchtgröße, Schotengröße, Schoten- oder Root growth, seed size, fruit size, pod size, pods or
Ährenzahl, Anzahl der Samen pro Schote oder Ähre, Samenmasse, verstärkte Ear number, number of seeds per pod or ear, seed mass, strengthened
Samenfüllung, verringerter Samenausfall, verringertes Schotenplatzen sowie Seed filling, reduced seed failure, reduced pod popping as well
Standfestigkeit. Zu weiteren Ertragsmerkmalen zählen Samenzusammensetzung wie Kohlenhydratgehalt, Proteingehalt, Ölgehalt und Ölzusammensetzung, Nährwert, Verringerung der nährwidrigen Verbindungen, verbesserte Verarbeitbarkeit und verbesserte Lagerfähigkeit.  Stability. Other yield-related traits include seed composition such as carbohydrate content, protein content, oil content and composition, nutritional value, reduction of nontoxic compounds, improved processability, and improved shelf life.
Pflanzen, die ebenfalls mit den erfindungsgemäßen Verbindungen der allgemeinen Formel (I) behandelt werden können, sind Hybridpflanzen, die bereits die Plants which can also be treated with the compounds of the general formula (I) according to the invention are hybrid plants which have already been used
Eigenschaften der Heterosis bzw. des Hybrideffekts exprimieren, was im allgemeinen zu höherem Ertrag, höherer Wüchsigkeit, besserer Gesundheit und besserer Characteristics of heterosis or hybrid effect, which generally results in higher yield, higher vigor, better health and better
Resistenz gegen biotische und abiotische Stressfaktoren führt. Solche Pflanzen werden typischerweise dadurch erzeugt, dass man eine ingezüchtete pollensterile Elternlinie (den weiblichen Kreuzungspartner) mit einer anderen ingezüchteten pollenfertilen Elternlinie (dem männlichen Kreuzungspartner) kreuzt. Das Resistance to biotic and abiotic stress factors. Such plants are typically produced by crossing an inbred male sterile parental line (the female crossover partner) with another inbred male fertile parent line (the male crossbred partner). The
Hybridsaatgut wird typischerweise von den pollensterilen Pflanzen geerntet und an Vermehrer verkauft. Pollensterile Pflanzen können manchmal (z. B. beim Mais) durch Entfahnen (d. h. mechanischem Entfernen der männlichen Geschlechtsorgane bzw. der männlichen Blüten), produziert werden; es ist jedoch üblicher, dass die Hybrid seed is typically harvested from the male sterile plants and sold to propagators. Pollen sterile plants can sometimes be produced (eg in maize) by delaving (i.e., mechanically removing male genitalia or male flowers); but it is more common that the
Pollensterilität auf genetischen Determinanten im Pflanzengenom beruht. In diesem Fall, insbesondere dann, wenn es sich bei dem gewünschten Produkt, da man von den Hybridpflanzen ernten will, um die Samen handelt, ist es üblicherweise günstig, sicherzustellen, dass die Pollenfertilität in Hybridpflanzen, die die für die Pollensterilität verantwortlichen genetischen Determinanten enthalten, völlig restoriert wird. Dies kann erreicht werden, indem sichergestellt wird, dass die männlichen Kreuzungspartner entsprechende Fertilitätsrestorergene besitzen, die in der Lage sind, die Pollenfertilität in Hybhdpflanzen, die die genetischen Determinanten, die für die Pollensterilität verantwortlich sind, enthalten, zu restorieren. Genetische Determinanten für Pollen sterility is based on genetic determinants in the plant genome. In this case, especially when the desired product, as one wants to harvest from the hybrid plants, is the seeds, it is usually beneficial to ensure that the pollen fertility in hybrid plants containing the genetic determinants responsible for male sterility , completely restored. This can be accomplished by ensuring that the male crossbrothers possess appropriate fertility restorer genes capable of controlling pollen fertility in hybrids containing the genetic determinants responsible for male sterility. Genetic determinants for
Pollensterilität können im Cytoplasma lokalisiert sein. Beispiele für cytoplasmatische Pollensterilität (CMS) wurden zum Beispiel für Brassica-Arten beschrieben (WO 92/005251 , WO 95/009910, WO 98/27806, WO 05/002324, WO 06/021972 und US 6,229,072). Genetische Determinanten für Pollensterilität können jedoch auch im Zellkerngenom lokalisiert sein. Pollensterile Pflanzen können auch mit Methoden der pflanzlichen Biotechnologie, wie Gentechnik, erhalten werden. Ein besonders günstiges Mittel zur Erzeugung von pollensterilen Pflanzen ist in WO 89/10396 beschrieben, wobei zum Beispiel eine Ribonuklease wie eine Barnase selektiv in den Tapetumzellen in den Staubblättern exprimiert wird. Die Fertilität kann dann durch Expression eines Ribonukleasehemmers wie Barstar in den Tapetumzellen restoriert werden (z. B. WO 91/002069). Pflanzen oder Pflanzensorten (die mit Methoden der Pflanzenbiotechnologie, wie der Gentechnik, erhalten werden), die ebenfalls mit den erfindungsgemäßen Pollen sterility may be localized in the cytoplasm. Examples of cytoplasmic male sterility (CMS) have been described, for example, for Brassica species (WO 92/005251, WO 95/009910, WO 98/27806, WO 05/002324, WO 06/021972 and US 6,229,072). However, genetic determinants of pollen sterility may also be localized in the nuclear genome. Pollen sterile plants can also be obtained using plant biotechnology methods such as genetic engineering. A particularly convenient means of producing male-sterile plants is described in WO 89/10396, wherein, for example, a ribonuclease such as a barnase is selectively expressed in the tapetum cells in the stamens. The fertility can then be restorated by expression of a ribonuclease inhibitor such as barstar in the tapetum cells (eg WO 91/002069). Plants or plant varieties (which are obtained by plant biotechnology methods, such as genetic engineering), which also with the inventive
Verbindungen der allgemeinen Formel (I) behandelt werden können, sind Compounds of general formula (I) can be treated are
herbizidtolerante Pflanzen, d. h. Pflanzen, die gegenüber einem oder mehreren vorgegebenen Herbiziden tolerant gemacht worden sind. Solche Pflanzen können entweder durch genetische Transformation oder durch Selektion von Pflanzen, die eine Mutation enthalten, die solch eine Herbizidtoleranz verleiht, erhalten werden. herbicide-tolerant plants, d. H. Plants tolerant to one or more given herbicides. Such plants can be obtained either by genetic transformation or by selection of plants containing a mutation conferring such herbicide tolerance.
Herbizidtolerante Pflanzen sind zum Beispiel glyphosatetolerante Pflanzen, d. h. Herbicide-tolerant plants are, for example, glyphosate-tolerant plants, i. H.
Pflanzen, die gegenüber dem Herbizid Glyphosate oder dessen Salzen tolerant gemacht worden sind. So können zum Beispiel glyphosatetolerante Pflanzen durch Transformation der Pflanze mit einem Gen, das für das Enzym 5-Enolpyruvylshikimat- 3-phosphatsynthase (EPSPS) kodiert, erhalten werden. Beispiele für solche EPSPS- Gene sind das AroA-Gen (Mutante CT7) des Bakterium Salmonella typhimurium (Comai et al., Science (1983), 221 , 370-371 ), das CP4-Gen des Bakteriums Plants tolerant to the herbicide glyphosate or its salts. For example, glyphosate-tolerant plants can be obtained by transforming the plant with a gene encoding the enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS). Examples of such EPSPS genes are the AroA gene (mutant CT7) of the bacterium Salmonella typhimurium (Comai et al., Science (1983), 221, 370-371), the CP4 gene of the bacterium
Agrobacterium sp. (Barry et al., Curr. Topics Plant Physiol. (1992), 7, 139-145), die Gene, die für eine EPSPS aus der Petunie (Shah et al., Science (1986), 233, 478- 481 ), für eine EPSPS aus der Tomate (Gasser et al., J. Biol. Chem. (1988), 263, 4280- 4289) oder für eine EPSPS aus Eleusine (WO 01/66704) kodieren. Es kann sich auch um eine mutierte EPSPS handeln, wie sie zum Beispiel in EP-A 0837944, WO 00/066746, WO 00/066747 oder WO 02/026995 beschrieben ist. Glyphosatetolerante Pflanzen können auch dadurch erhalten werden, dass man ein Gen exprimiert, das für ein Glyphosate-Oxidoreduktase-Enzym, wie es in US 5,776,760 und US 5,463,175 beschrieben ist, kodiert. Glyphosatetolerante Pflanzen können auch dadurch erhalten werden, dass man ein Gen exprimiert, das für ein Glyphosate-acetyltransferase- Enzym, wie es in z. B. WO 02/036782, WO 03/092360, WO 05/012515 und WO Agrobacterium sp. (Barry et al., Curr Topics Plant Physiol. (1992), 7, 139-145), the genes responsible for petunia EPSPS (Shah et al., Science (1986), 233, 478-481). , for a EPSPS from the tomato (Gasser et al., J. Biol. Chem. (1988), 263, 4280- 4289) or for an EPSPS from Eleusine (WO 01/66704) encode. It may also be a mutated EPSPS, as described for example in EP-A 0837944, WO 00/066746, WO 00/066747 or WO 02/026995. Glyphosate-tolerant plants can also be obtained by expressing a gene coding for a glyphosate oxidoreductase enzyme as described in US 5,776,760 and US 5,463,175. Glyphosate-tolerant plants may also be obtained by expressing a gene encoding a glyphosate acetyltransferase enzyme as described in, e.g. WO 02/036782, WO 03/092360, WO 05/012515 and WO
07/024782 beschrieben ist, kodiert. Glyphosatetolerante Pflanzen können auch dadurch erhalten werden, dass man Pflanzen, die natürlich vorkommende Mutationen der oben erwähnten Gene, wie sie zum Beispiel in WO 01/024615 oder WO 07/024782 is encoded. Glyphosate-tolerant plants can also be obtained by culturing plants containing the naturally occurring mutations of the above-mentioned genes, as described, for example, in WO 01/024615 or WO
03/013226 beschrieben sind, enthalten, selektiert. 03/013226 are described, contained, selected.
Sonstige herbizidresistente Pflanzen sind zum Beispiel Pflanzen, die gegenüber Herbiziden, die das Enzym Glutaminsynthase hemmen, wie Bialaphos, Phosphinotricin oder Glufosinate, tolerant gemacht worden sind. Solche Pflanzen können dadurch erhalten werden, dass man ein Enzym exprimiert, das das Herbizid oder eine Mutante des Enzyms Glutaminsynthase, das gegenüber Hemmung resistent ist, entgiftet. Solch ein wirksames entgiftendes Enzym ist zum Beispiel ein Enzym, das für ein Other herbicide-resistant plants are, for example, plants which have been tolerated to herbicides which inhibit the enzyme glutamine synthase, such as bialaphos, phosphinotricin or glufosinate. Such plants can be obtained by expressing an enzyme which detoxifies the herbicide or a mutant of the enzyme glutamine synthase, which is resistant to inhibition. Such an effective detoxifying enzyme is, for example, an enzyme suitable for
Phosphinotricin-acetyltransferase kodiert (wie zum Beispiel das bar- oder pat-Protein aus Streptomyces-Arten). Pflanzen, die eine exogene Phosphinotricin- acetyltransferase exprimieren, sind zum Beispiel in US 5,561 ,236; US 5,648,477; US 5,646,024; US 5,273,894; US 5,637,489; US 5,276,268; US 5,739,082; US 5,908,810 und US 7,1 12,665 beschrieben. Phosphinotricin acetyltransferase encoded (such as the bar or pat protein from Streptomyces species). Plants expressing an exogenous phosphinotricin acetyltransferase are described, for example, in US 5,561,236; US 5,648,477; US 5,646,024; US 5,273,894; US 5,637,489; US 5,276,268; US 5,739,082; US 5,908,810 and US 7,112,665.
Weitere herbizidtolerante Pflanzen sind auch Pflanzen, die gegenüber den Herbiziden, die das Enzym Hydroxyphenylpyruvatdioxygenase (HPPD) hemmen, tolerant gemacht worden sind. Bei den Hydroxyphenylpyruvatdioxygenasen handelt es sich um Enzyme, die die Reaktion, in der para-Hydroxyphenylpyruvat (HPP) zu Homogentisat umgesetzt wird, katalysieren. Pflanzen, die gegenüber HPPD-Hemmern tolerant sind, können mit einem Gen, das für ein natürlich vorkommendes resistentes HPPD-Enzym kodiert, oder einem Gen, das für ein mutiertes HPPD-Enzym gemäß WO 96/038567, WOFurther herbicide-tolerant plants are also plants tolerant to the herbicides which inhibit the enzyme hydroxyphenylpyruvate dioxygenase (HPPD). The hydroxyphenylpyruvate dioxygenases are enzymes that catalyze the reaction in which para-hydroxyphenylpyruvate (HPP) is converted to homogentisate. Plants tolerant to HPPD inhibitors may be treated with a gene encoding a naturally occurring resistant HPPD enzyme or a gene encoding a mutant HPPD enzyme according to WO 96/038567, WO
99/024585 und WO 99/024586 kodiert, transformiert werden. Eine Toleranz gegenüber HPPD-Hemmern kann auch dadurch erzielt werden, dass man Pflanzen mit Genen transformiert, die für gewisse Enzyme kodieren, die die Bildung von Homogentisat trotz Hemmung des nativen HPPD-Enzyms durch den HPPD-Hemmer ermöglichen. Solche Pflanzen und Gene sind in WO 99/034008 und WO 2002/36787 beschrieben. Die Toleranz von Pflanzen gegenüber HPPD-Hemmern kann auch dadurch verbessert werden, dass man Pflanzen zusätzlich zu einem Gen, das für ein HPPD-tolerantes Enzym kodiert, mit einem Gen transformiert, das für ein Prephenatdehydrogenase- Enzym kodiert, wie dies in WO 2004/024928 beschrieben ist. 99/024585 and WO 99/024586. Tolerance to HPPD inhibitors can also be achieved by transforming plants with genes encoding certain enzymes that allow the formation of homogentisate despite inhibition of the native HPPD enzyme by the HPPD inhibitor. Such plants and genes are described in WO 99/034008 and WO 2002/36787. The tolerance of plants to HPPD inhibitors can also be improved by transforming plants, in addition to a gene which codes for an HPPD-tolerant enzyme, with a gene which codes for a prephenate dehydrogenase enzyme, as described in WO 2004 / 024928 is described.
Weitere herbizidresistente Pflanzen sind Pflanzen, die gegenüber Acetolactatsynthase (ALS)-Hemmern tolerant gemacht worden sind. Zu bekannten ALS-Hemmern zählen zum Beispiel Sulfonylharnstoff, Imidazolinon, Triazolopyrimidine, Other herbicide-resistant plants are plants that have been tolerated to acetolactate synthase (ALS) inhibitors. Examples of known ALS inhibitors include sulfonylurea, imidazolinone, triazolopyrimidines,
Pyrimidinyloxy(thio)benzoate und/oder Sulfonylaminocarbonyltriazolinon-Herbizide. Es ist bekannt, dass verschiedene Mutationen im Enzym ALS (auch als Pyrimidinyloxy (thio) benzoates and / or sulfonylaminocarbonyltriazolinone herbicides. It is known that various mutations in the enzyme ALS (also known as
Acetohydroxysäure-Synthase, AHAS, bekannt) eine Toleranz gegenüber Acetohydroxy acid synthase, AHAS, known) a tolerance to
unterschiedlichen Herbiziden bzw. Gruppen von Herbiziden verleihen, wie dies zum Beispiel bei Tranel und Wright, Weed Science (2002), 50, 700-712, jedoch auch in US 5,605,01 1 , US 5,378,824, US 5,141 ,870 und US 5,013,659, beschrieben ist. Die Herstellung von sulfonylharnstofftoleranten Pflanzen und imidazolinontoleranten Pflanzen ist in US 5,605,01 1 ; US 5,013,659; US 5,141 ,870; US 5,767,361 ; US different herbicides or groups of herbicides, as described, for example, by Tranel and Wright, Weed Science (2002), 50, 700-712, but also in US Pat. Nos. 5,605,011, 5,378,824, 5,141,870 and 5,013,659. is described. The preparation of sulfonylurea tolerant plants and imidazolinone tolerant plants is described in US 5,605,011 1; US 5,013,659; US 5,141,870; US 5,767,361; US
5,731 ,180; US 5,304,732; US 4,761 ,373; US 5,331 ,107; US 5,928,937; und US 5,731,180; US 5,304,732; US 4,761,373; US 5,331, 107; US 5,928,937; and US
5,378,824; sowie in der internationalen Veröffentlichung WO 96/033270 beschrieben. Weitere imidazolinontolerante Pflanzen sind auch in z. B. WO 2004/040012, WO 2004/106529, WO 2005/020673, WO 2005/093093, WO 2006/007373, WO 5,378,824; and in international publication WO 96/033270. Other imidazolinontolerante plants are also in z. WO 2004/040012, WO 2004/106529, WO 2005/020673, WO 2005/093093, WO 2006/007373, WO
2006/015376, WO 2006/024351 und WO 2006/060634 beschrieben. Weitere 2006/015376, WO 2006/024351 and WO 2006/060634. Further
Sulfonylharnstoff- und imidazolinontolerante Pflanzen sind auch in z.B. WO Sulfonylurea and imidazolinone tolerant plants are also useful in e.g. WHERE
2007/024782 beschrieben. 2007/024782 described.
Weitere Pflanzen, die gegenüber ALS-Inhibitoren, insbesondere gegenüber Other plants that are resistant to ALS inhibitors, especially against
Imidazolinonen, Sulfonylharnstoffen und/oder Sulfamoylcarbonyltriazolinonen tolerant sind, können durch induzierte Mutagenese, Selektion in Zellkulturen in Gegenwart des Herbizids oder durch Mutationszüchtung erhalten werden, wie dies zum Beispiel für die Sojabohne in US 5,084,082, für Reis in WO 97/41218, für die Zuckerrübe in US 5,773,702 und WO 99/057965, für Salat in US 5,198,599 oder für die Sonnenblume in WO 2001/065922 beschrieben ist. Pflanzen oder Pflanzensorten (die nach Methoden der pflanzlichen Biotechnologie, wie der Gentechnik, erhalten wurden), die ebenfalls mit den erfindungsgemäßen Imidazolinones, sulfonylureas and / or sulfamoylcarbonyltriazolinones, can be obtained by induced mutagenesis, selection in cell cultures in the presence of the herbicide or by mutation breeding, as for example for the soybean in US 5,084,082, for rice in WO 97/41218, for the sugar beet in US 5,773,702 and WO 99/057965, for salad in US 5,198,599 or for the sunflower in WO 2001/065922. Plants or plant varieties (obtained by plant biotechnology methods, such as genetic engineering), which are also with the inventive
Verbindungen der allgemeinen Formel (I) behandelt werden können, sind Compounds of general formula (I) can be treated are
insektenresistente transgene Pflanzen, d.h. Pflanzen, die gegen Befall mit gewissen Zielinsekten resistent gemacht wurden. Solche Pflanzen können durch genetische Transformation oder durch Selektion von Pflanzen, die eine Mutation enthalten, die solch eine Insektenresistenz verleiht, erhalten werden. insect-resistant transgenic plants, i. Plants that have been made resistant to attack by certain target insects. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such insect resistance.
Der Begriff "insektenresistente transgene Pflanze" umfasst im vorliegenden The term "insect-resistant transgenic plant" as used herein
Zusammenhang jegliche Pflanze, die mindestens ein Transgen enthält, das eine Kodiersequenz umfasst, die für folgendes kodiert: Relates to any plant containing at least one transgene comprising a coding sequence coding for:
1 ) ein Insektizides Kristallprotein aus Bacillus thuringiensis oder einen Insektiziden Teil davon, wie die Insektiziden Kristallproteine, die von Crickmore et al., Microbiology and Molecular Biology Reviews (1998), 62, 807-813, zusammengestellt wurden, von Crickmore et al. (2005) in der Bacillus thuringiensis-Toxinnomenklatur aktualisiert (online bei: 1) an insecticidal crystal protein from Bacillus thuringiensis or an insecticidal portion thereof, such as the insecticidal crystal proteins collected by Crickmore et al., Microbiology and Molecular Biology Reviews (1998), 62, 807-813, by Crickmore et al. (2005) in the Bacillus thuringiensis toxin nomenclature (online at:
http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/), oder Insektizide Teile davon, z.B. Proteine der Cry-Proteinklassen CrylAb, CrylAc, Cryl F, Cry2Ab, Cry3Ae oder Cry3Bb oder Insektizide Teile davon; oder http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/), or insecticidal parts thereof, e.g. Proteins of Cry protein classes CrylAb, CrylAc, Cryl F, Cry2Ab, Cry3Ae or Cry3Bb or insecticidal parts thereof; or
2) ein Kristallprotein aus Bacillus thuringiensis oder einen Teil davon, der in Gegenwart eines zweiten, anderen Kristallproteins als Bacillus thuringiensis oder eines Teils davon insektizid wirkt, wie das binäre Toxin, das aus den Kristallproteinen Cy34 und Cy35 besteht (Moellenbeck et al., Nat. Biotechnol. (2001 ), 19, 668-72; Schnepf et al., Applied Environm. Microb. (2006), 71 , 1765-1774); oder 2) a crystal protein from Bacillus thuringiensis or a part thereof which is insecticidal in the presence of a second, different crystal protein than Bacillus thuringiensis or a part thereof, such as the binary toxin consisting of the crystal proteins Cy34 and Cy35 (Moellenbeck et al., Nat Biotechnol. (2001), 19, 668-72; Schnepf et al., Applied Environment Microb. (2006), 71, 1765-1774); or
3) ein Insektizides Hybridprotein, das Teile von zwei unterschiedlichen Insektiziden Kristallproteinen aus Bacillus thuringiensis umfasst, wie zum Beispiel ein Hybrid aus den Proteinen von 1 ) oben oder ein Hybrid aus den Proteinen von 2) oben, z. B. das Protein Cry1A.105, das von dem Mais-Event MON98034 produziert wird (WO 3) an insecticidal hybrid protein comprising parts of two different insecticides of Bacillus thuringiensis crystal proteins, such as a hybrid of the proteins of 1) above or a hybrid of the proteins of 2) above, e.g. For example, the protein Cry1A.105 produced by the corn event MON98034 (WO
2007/027777); oder 4) ein Protein gemäß einem der Punkte 1 ) bis 3) oben, in dem einige, insbesondere 1 bis 10, Aminosäuren durch eine andere Aminosäure ersetzt wurden, um eine höhere Insektizide Wirksamkeit gegenüber einer Zielinsektenart zu erzielen und/oder um das Spektrum der entsprechenden Zielinsektenarten zu erweitern und/oder wegen Veränderungen, die in die Kodier- DNA während der Klonierung oder Transformation induziert wurden, wie das Protein Cry3Bb1 in Mais-Events MON863 oder MON88017 oder das Protein Cry3A im Mais-Event MIR 604; oder 2007/027777); or 4) a protein according to any one of items 1) to 3) above, in which some, in particular 1 to 10, amino acids have been replaced by another amino acid to achieve a higher insecticidal activity against a target insect species and / or the spectrum of the corresponding To expand target insect species and / or due to changes induced in the coding DNA during cloning or transformation, such as the protein Cry3Bb1 in maize events MON863 or MON88017 or the protein Cry3A in the maize event MIR 604; or
5) ein Insektizides sezerniertes Protein aus Bacillus thuringiensis oder Bacillus cereus oder einen Insektiziden Teil davon, wie die vegetativ wirkenden 5) an insecticidal secreted protein from Bacillus thuringiensis or Bacillus cereus or an insecticidal part thereof, such as the vegetative
insektentoxischen Proteine (vegetative insecticidal proteins, VIP), die unter folgendem Link angeführt sind, z. B. Proteine der Proteinklasse VIP3Aa: insecticidal proteins (VIP) listed under the following link, e.g. B. Proteins of protein class VIP3Aa:
http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/vip.html oder 6) ein sezerniertes Protein aus Bacillus thuringiensis oder Bacillus cereus, das in Gegenwart eines zweiten sezernierten Proteins aus Bacillus thuringiensis oder B. cereus insektizid wirkt, wie das binäre Toxin, das aus den Proteinen VIP1A und VIP2A besteht (WO 94/21795); oder 7) ein Insektizides Hybridprotein, das Teile von verschiedenen sezerniertenhttp://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/vip.html or 6) a secreted protein from Bacillus thuringiensis or Bacillus cereus, which is expressed in the presence of a second secreted protein from Bacillus thuringiensis or B. cereus insecticide, such as the binary toxin consisting of the proteins VIP1A and VIP2A (WO 94/21795); or 7) an insecticidal hybrid protein that secretes parts of various
Proteinen von Bacillus thuringiensis oder Bacillus cereus umfasst, wie ein Hybrid der Proteine von 1 ) oder ein Hybrid der Proteine von 2) oben; oder Proteins of Bacillus thuringiensis or Bacillus cereus, such as a hybrid of the proteins of 1) or a hybrid of the proteins of 2) above; or
8) ein Protein gemäß einem der Punkte 1 ) bis 3) oben, in dem einige, 8) a protein according to any one of items 1) to 3) above, in which some,
insbesondere 1 bis 10, Aminosäuren durch eine andere Aminosäure ersetzt wurden, um eine höhere Insektizide Wirksamkeit gegenüber einer Zielinsektenart zu erzielen und/oder um das Spektrum der entsprechenden Zielinsektenarten zu erweitern und/oder wegen Veränderungen, die in die Kodier- DNA während der Klonierung oder Transformation induziert wurden (wobei die Kodierung für ein Insektizides Protein erhalten bleibt), wie das Protein VIP3Aa im Baumwoll-Event COT 102. In particular, 1 to 10, amino acids have been replaced by another amino acid to achieve higher insecticidal activity against a target insect species and / or to broaden the spectrum of the corresponding target insect species and / or due to changes in the coding DNA during cloning or Transformation (retaining coding for an insecticidal protein) such as protein VIP3Aa in cotton event COT 102.
Natürlich zählt zu den insektenresistenten transgenen Pflanzen im vorliegenden Zusammenhang auch jegliche Pflanze, die eine Kombination von Genen umfasst, die für die Proteine von einer der oben genannten Klassen 1 bis 8 kodieren. In einer Ausführungsform enthält eine insektenresistente Pflanze mehr als ein Transgen, das für ein Protein nach einer der oben genannten 1 bis 8 kodiert, um das Spektrum der entsprechenden Zielinsektenarten zu erweitern oder um die Entwicklung einer Of course, insect-resistant transgenic plants in the present context also include any plant comprising a combination of genes encoding the proteins of any of the above classes 1 to 8. In a Embodiment contains an insect-resistant plant more than a transgene encoding a protein according to any one of the above 1 to 8, in order to expand the spectrum of the corresponding target insect species or to the development of a
Resistenz der Insekten gegen die Pflanzen dadurch hinauszuzögern, dass man verschiedene Proteine einsetzt, die für dieselbe Zielinsektenart insektizid sind, jedoch eine unterschiedliche Wirkungsweise, wie Bindung an unterschiedliche To delay insect resistance to plants by using different proteins which are insecticidal for the same target insect species, but a different mode of action, such as binding to different ones
Rezeptorbindungsstellen im Insekt, aufweisen. Receptor binding sites in the insect.
Pflanzen oder Pflanzensorten (die nach Methoden der pflanzlichen Biotechnologie, wie der Gentechnik, erhalten wurden), die ebenfalls mit den erfindungsgemäßen Plants or plant varieties (obtained by plant biotechnology methods, such as genetic engineering), which are also with the inventive
Verbindungen der allgemeinen Formel (I) behandelt werden können, sind gegenüber abiotischen Stressfaktoren tolerant. Solche Pflanzen können durch genetische  Compounds of general formula (I) are tolerant to abiotic stressors. Such plants can be caused by genetic
Transformation oder durch Selektion von Pflanzen, die eine Mutation enthalten, die solch eine Stressresistenz verleiht, erhalten werden. Zu besonders nützlichen Pflanzen mit Stresstoleranz zählen folgende: a. Pflanzen, die ein Transgen enthalten, das die Expression und/oder Aktivität des Gens für die Poly(ADP-ribose)polymerase (PARP) in den Pflanzenzellen oder Transformation or selection of plants containing a mutation conferring such stress resistance. Particularly useful plants with stress tolerance include the following: a. Plants which contain a transgene which have the expression and / or activity of the gene for the poly (ADP-ribose) polymerase (PARP) in the plant cells or
Pflanzen zu reduzieren vermag, wie dies in WO 2000/004173 oder EP 04077984.5 oder EP 06109836.5 beschrieben ist. b. Pflanzen, die ein stresstoleranzförderndes Transgen enthalten, das die To reduce plants, as described in WO 2000/004173 or EP 04077984.5 or EP 06109836.5. b. Plants that contain a stress tolerance enhancing transgene that the
Expression und/oder Aktivität der für PARG kodierenden Gene der Pflanzen oder Pflanzenzellen zu reduzieren vermag, wie dies z.B. in WO 2004/090140 beschrieben ist; c. Pflanzen, die ein stresstoleranzförderndes Transgen enthalten, das für ein in Pflanzen funktionelles Enzym des Nicotinamidadenindinukleotid-Salvage- Biosynthesewegs kodiert, darunter Nicotinamidase, To reduce expression and / or activity of PARG-encoding genes of plants or plant cells, as described e.g. in WO 2004/090140 is described; c. Plants which contain a stress tolerance enhancing transgene encoding a plant functional enzyme of the nicotinamide adenine dinucleotide salvage biosynthetic pathway, including nicotinamidase,
Nicotinatphosphoribosyltransferase, Nicotinsäuremononukleotid-adenyltransferase, Nicotinamidadenindinukleotidsynthetase oder Nicotinamidphosphoribosyl-transferase, wie dies z. B. in EP 04077624.7 oder WO 2006/133827 oder PCT/EP07/002433 beschrieben ist. Pflanzen oder Pflanzensorten (die nach Methoden der pflanzlichen Biotechnologie, wie der Gentechnik, erhalten wurden), die ebenfalls mit den erfindungsgemäßen Nicotinate phosphoribosyltransferase, nicotinic acid mononucleotide adenyltransferase, nicotinamide adenine dinucleotide synthetase or nicotinamide phosphoribosyltransferase, as described e.g. As described in EP 04077624.7 or WO 2006/133827 or PCT / EP07 / 002433. Plants or plant varieties (obtained by plant biotechnology methods, such as genetic engineering), which are also with the inventive
Verbindungen der allgemeinen Formel (I) behandelt werden können, weisen eine veränderte Menge, Qualität und/oder Lagerfähigkeit des Ernteprodukts und/oder veränderte Eigenschaften von bestimmten Bestandteilen des Ernteprodukts auf, wie zum Beispiel: Compounds of general formula (I) may have an altered amount, quality and / or shelf life of the crop and / or altered properties of certain components of the crop, such as:
1 ) Transgene Pflanzen, die eine modifizierte Stärke synthetisieren, die bezüglich ihrer chemisch-physikalischen Eigenschaften, insbesondere des Amylosegehalts oder des Amylose/Amylopektin-Verhältnisses, des Verzweigungsgrads, der 1) Transgenic plants that synthesize a modified starch, with respect to their chemical-physical properties, in particular the amylose content or the amylose / amylopectin ratio, the degree of branching, the
durchschnittlichen Kettenlänge, der Verteilung der Seitenketten, des average chain length, the distribution of side chains, the
Viskositätsverhaltens, der Gelfestigkeit, der Stärkekorngröße und/oder Viscosity behavior, the gel strength, the starch grain size and / or
Stärkekornmorphologie im Vergleich mit der synthetisierten Stärke in Starch grain morphology in comparison with the synthesized starch in
Wildtyppflanzenzellen oder -pflanzen verändert ist, so dass sich diese modifizierte Stärke besser für bestimmte Anwendungen eignet. Diese transgenen Pflanzen, die eine modifizierte Stärke synthetisieren, sind zum Beispiel in EP 0571427, WO Wild-type plant cells or plants, so that this modified starch is better suited for certain applications. These transgenic plants synthesizing a modified starch are described, for example, in EP 0571427, WO
95/004826, EP 0719338, WO 96/15248, WO 96/19581 , WO 96/27674, WO 97/1 1 188, WO 97/26362, WO 97/32985, WO 97/42328, WO 97/44472, WO 97/45545, WO 98/27212, WO 98/40503, WO 99/58688, WO 99/58690, WO 99/58654, WO 95/004826, EP 0719338, WO 96/15248, WO 96/19581, WO 96/27674, WO 97/1 1 188, WO 97/26362, WO 97/32985, WO 97/42328, WO 97/44472, WO 97/45545, WO 98/27212, WO 98/40503, WO 99/58688, WO 99/58690, WO 99/58654, WO
2000/008184, WO 2000/008185, WO 2000/28052, WO 2000/77229, WO 2001/12782, WO 2001/12826, WO 2002/101059, WO 2003/071860, 2000/008184, WO 2000/008185, WO 2000/28052, WO 2000/77229, WO 2001/12782, WO 2001/12826, WO 2002/101059, WO 2003/071860,
WO 2004/056999, WO 2005/030942, WO 2005/030941 , WO 2005/095632, WO 2004/056999, WO 2005/030942, WO 2005/030941, WO 2005/095632,
WO 2005/095617, WO 2005/095619, WO 2005/095618, WO 2005/123927, WO 2005/095617, WO 2005/095619, WO 2005/095618, WO 2005/123927,
WO 2006/018319, WO 2006/103107, WO 2006/108702, WO 2007/009823, WO 2006/018319, WO 2006/103107, WO 2006/108702, WO 2007/009823,
WO 2000/22140, WO 2006/063862, WO 2006/072603, WO 2002/034923, WO 2000/22140, WO 2006/063862, WO 2006/072603, WO 2002/034923,
EP 06090134.5, EP 06090228.5, EP 06090227.7, EP 07090007.1 , EP 07090009.7, WO 2001/14569, WO 2002/79410, WO 2003/33540, WO 2004/078983,  EP 06090134.5, EP 06090228.5, EP 06090227.7, EP 07090007.1, EP 07090009.7, WO 2001/14569, WO 2002/79410, WO 2003/33540, WO 2004/078983,
WO 2001/19975, WO 95/26407, WO 96/34968, WO 98/20145, WO 99/12950, WO 2001/19975, WO 95/26407, WO 96/34968, WO 98/20145, WO 99/12950,
WO 99/66050, WO 99/53072, US 6,734,341 , WO 2000/1 1 192, WO 98/22604, WO 99/66050, WO 99/53072, US 6,734,341, WO 2000/1 1 192, WO 98/22604,
WO 98/32326, WO 2001/98509, WO 2001/98509, WO 2005/002359, US 5,824,790, US 6,013,861 , WO 94/004693, WO 94/009144, WO 94/1 1520, WO 95/35026 bzw. WO 97/20936 beschrieben. 2) Transgene Pflanzen, die Nichtstärkekohlenhydratpolymere synthetisieren, oder Nichtstärkekohlenhydratpolymere, deren Eigenschaften im Vergleich zu WO 98/32326, WO 2001/98509, WO 2001/98509, WO 2005/002359, US 5,824,790, US Pat. No. 6,013,861, WO 94/004693, WO 94/009144, WO 94/1 1520, WO 95/35026 and WO 97, respectively / 20936. 2) Transgenic plants that synthesize non-starch carbohydrate polymers, or non-starch carbohydrate polymers whose properties are compared to
Wildtyppflanzen ohne genetische Modifikation verändert sind. Beispiele sind Pflanzen, die Polyfructose, insbesondere des Inulin- und Levantyps, produzieren, wie dies in EP 0663956, WO 96/001904, WO 96/021023, WO 98/039460 und Wildtype plants are modified without genetic modification. Examples are plants which produce polyfructose, in particular of the inulin and levan type, as described in EP 0663956, WO 96/001904, WO 96/021023, WO 98/039460 and
WO 99/024593 beschrieben ist, Pflanzen, die alpha-1 ,4-Glucane produzieren, wie dies in WO 95/031553, US 2002/031826, US 6,284,479, US 5,712,107,  WO 99/024593, plants which produce alpha-1, 4-glucans, as described in WO 95/031553, US 2002/031826, US 6,284,479, US 5,712,107,
WO 97/047806, WO 97/047807, WO 97/047808 und WO 2000/14249 beschrieben ist, Pflanzen, die alpha-1 ,6-verzweigte alpha-1 ,4-Glucane produzieren, wie dies in WO 2000/73422 beschrieben ist, und Pflanzen, die Alternan produzieren, wie dies in WO 2000/047727, EP 06077301 .7, US 5,908,975 und EP 0728213 beschrieben ist. WO 97/047806, WO 97/047807, WO 97/047808 and WO 2000/14249, plants which produce alpha-1, 6-branched alpha-1, 4-glucans, as described in WO 2000/73422 , and plants that produce alternan, as described in WO 2000/047727, EP 06077301.7, US 5,908,975 and EP 0728213.
3) Transgene Pflanzen, die Hyaluronan produzieren, wie dies zum Beispiel in WO 06/032538, WO 2007/039314, WO 2007/039315, WO 2007/039316, 3) Transgenic plants producing hyaluronan, as described for example in WO 06/032538, WO 2007/039314, WO 2007/039315, WO 2007/039316,
JP 2006/304779 und WO 2005/012529 beschrieben ist. JP 2006/304779 and WO 2005/012529.
Pflanzen oder Pflanzensorten (die nach Methoden der pflanzlichen Biotechnologie, wie der Gentechnik, erhalten wurden), die ebenfalls mit den erfindungsgemäßen Plants or plant varieties (obtained by plant biotechnology methods, such as genetic engineering), which are also with the inventive
Verbindungen der allgemeinen Formel (I) behandelt werden können, sind Pflanzen wie Baumwollpflanzen mit veränderten Fasereigenschaften. Solche Pflanzen können durch genetische Transformation oder durch Selektion von Pflanzen, die eine Mutation enthalten, die solche veränderten Fasereigenschaften verleiht, erhalten werden; dazu zählen: a) Pflanzen wie Baumwollpflanzen, die eine veränderte Form von Compounds of general formula (I) can be treated are plants such as cotton plants with altered fiber properties. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such altered fiber properties; These include: a) plants, such as cotton plants, which have an altered form of
Cellulosesynthasegenen enthalten, wie dies in WO 98/000549 beschrieben ist, b) Pflanzen wie Baumwollpflanzen, die eine veränderte Form von rsw2- oder rsw3- homologen Nukleinsäuren enthalten, wie dies in WO 2004/053219 beschrieben ist; c) Pflanzen wie Baumwollpflanzen mit einer erhöhten Expression der  Contain cellulose synthase genes, as described in WO 98/000549, b) plants such as cotton plants containing an altered form of rsw2 or rsw3 homologous nucleic acids, as described in WO 2004/053219; c) plants such as cotton plants with an increased expression of the
Saccharosephosphatsynthase, wie dies in WO 2001/017333 beschrieben ist; d) Pflanzen wie Baumwollpflanzen mit einer erhöhten Expression der Saccharosesynthase, wie dies in WO 02/45485 beschrieben ist; e) Pflanzen wie Baumwollpflanzen bei denen der Zeitpunkt der Sucrose phosphate synthase as described in WO 2001/017333; d) plants such as cotton plants with an increased expression of sucrose synthase, as described in WO 02/45485; e) plants such as cotton plants where the date of
Durchlasssteuerung der Plasmodesmen an der Basis der Faserzelle verändert ist, z. B. durch Herunterregulieren der faserselektiven ß-1 ,3-Glucanase, wie dies in Transmission control of the Plasmodesmen is changed at the base of the fiber cell, z. By downregulating the fiber-selective β-1,3-glucanase, as described in U.S. Patent No. 5,348,786
WO 2005/017157 beschrieben ist; f) Pflanzen wie Baumwollpflanzen mit Fasern mit veränderter Reaktivität, z. B. durch Expression des N-Acetylglucosamintransferasegens, darunter auch nodC, und von Chitinsynthasegenen, wie dies in WO 2006/136351 beschrieben ist. WO 2005/017157 is described; f) plants such as cotton plants with modified reactivity fibers, e.g. By expression of the N-acetylglucosamine transferase gene, including nodC, and chitin synthase genes, as described in WO 2006/136351.
Pflanzen oder Pflanzensorten (die nach Methoden der pflanzlichen Biotechnologie, wie der Gentechnik, erhalten wurden), die ebenfalls mit den erfindungsgemäßen Plants or plant varieties (obtained by plant biotechnology methods, such as genetic engineering), which are also with the inventive
Verbindungen der allgemeinen Formel (I) behandelt werden können, sind Pflanzen wie Raps oder verwandte Brassica-Pflanzen mit veränderten Eigenschaften der Compounds of general formula (I) can be treated are plants such as rapeseed or related Brassica plants with altered properties of
Ölzusammensetzung. Solche Pflanzen können durch genetische Transformation oder durch Selektion von Pflanzen, die eine Mutation enthalten, die solche veränderten Öleigenschaften verleiht, erhalten werden; dazu zählen: a) Pflanzen wie Rapspflanzen, die Öl mit einem hohen Ölsäuregehalt produzieren, wie dies zum Beispiel in US 5,969,169, US 5,840,946 oder Oil composition. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such altered oil properties; These include: a) plants such as rape plants that produce high oleic oil, as described, for example, in US 5,969,169; US 5,840,946;
US 6,323,392 oder US 6,063, 947 beschrieben ist; b) Pflanzen wie Rapspflanzen, die Öl mit einem niedrigen Linolensäuregehalt produzieren, wie dies in US 6,270828, US 6,169,190 oder US 5,965,755 beschrieben ist. c) Pflanzen wie Rapspflanzen, die Öl mit einem niedrigen gesättigten US 6,323,392 or US 6,063,947; b) plants such as oilseed rape plants which produce low linolenic acid oil, as described in US 6,270,828, US 6,169,190 or US 5,965,755. c) plants such as rape plants, the oil with a low saturated
Fettsäuregehalt produzieren, wie dies z. B. in US 5,434,283 beschrieben ist. Produce fatty acid content, as z. As described in US 5,434,283.
Besonders nützliche transgene Pflanzen, die mit den erfindungsgemäßen Particularly useful transgenic plants with the inventive
Verbindungen der allgemeinen Formel (I) behandelt werden können, sind Pflanzen, die Transformations-Events, oder eine Kombination von Transformations-Events, enthalten und die zum Beispiel in den Dateien von verschiedenen nationalen oder regionalen Behörden angeführt sind. Besonders nützliche transgene Pflanzen, die mit den erfindungsgemäßen Compounds of general formula (I) can be treated are plants which Transformation events, or a combination of transformation events, included, for example, in the files of various national or regional authorities. Particularly useful transgenic plants with the inventive
Verbindungen der allgemeinen Formel (I) behandelt werden können, sind beispielhaft Pflanzen mit einem oder mehreren Genen, die für ein oder mehrere Toxine kodieren, sind die transgenen Pflanzen, die unter den folgenden Handelsbezeichnungen angeboten werden: YIELD GARD® (zum Beispiel Mais, Baumwolle, Sojabohnen), KnockOut® (zum Beispiel Mais), BiteGard® (zum Beispiel Mais), BT-Xtra® (zum Beispiel Mais), StarLink® (zum Beispiel Mais), Bollgard® (Baumwolle), Nucotn® (Baumwolle), Nucotn 33B® (Baumwolle), NatureGard® (zum Beispiel Mais),  Exemplary plants having one or more genes encoding one or more toxins are the transgenic plants available under the following tradenames: YIELD GARD® (for example, corn, cotton , Soybeans), KnockOut® (for example corn), BiteGard® (for example maize), BT-Xtra® (for example maize), StarLink® (for example corn), Bollgard® (cotton), Nucotn® (cotton), Nucotn 33B® (cotton), NatureGard® (for example corn),
Protecta® und NewLeaf® (Kartoffel). Herbizidtolerante Pflanzen, die zu erwähnen sind, sind zum Beispiel Maissorten, Baumwollsorten und Sojabohnensorten, die unter den folgenden Handelsbezeichnungen angeboten werden: Roundup Ready® Protecta® and NewLeaf® (potato). Herbicide-tolerant crops to be mentioned include, for example, corn, cotton and soybean varieties sold under the following tradenames: Roundup Ready®
(Glyphosatetoleranz, zum Beispiel Mais, Baumwolle, Sojabohne), Liberty Link® (Phosphinotricintoleranz, zum Beispiel Raps), IMI® (Imidazolinontoleranz) und SCS® (Sylfonylharnstofftoleranz), zum Beispiel Mais. Zu den herbizidresistenten Pflanzen (traditionell auf Herbizidtoleranz gezüchtete Pflanzen), die zu erwähnen sind, zählen die unter der Bezeichnung Clearfield® angebotenen Sorten (zum Beispiel Mais). (Glyphosate tolerance, for example corn, cotton, soybean), Liberty Link® (phosphinotricin tolerance, for example rapeseed), IMI® (imidazolinone tolerance) and SCS® (sylphonylurea tolerance), for example maize. Herbicide-resistant plants (plants traditionally grown for herbicide tolerance) to be mentioned include the varieties sold under the name Clearfield® (for example corn).
Die erfindungsgemäßen Verbindungen der Formel (I) können in übliche The compounds of the formula (I) according to the invention can be prepared in conventional
Formulierungen überführt werden, wie Lösungen, Emulsionen, Spritzpulver, wasser- und ölbasierte Suspensionen, Pulver, Stäubemittel, Pasten, lösliche Pulver, lösliche Granulate, Streugranulate, Suspensions-Emulsions-Konzentrate, Wirkstoff-imprägnierte Naturstoffe, Wirkstoff-imprägnierte synthetische Stoffe, Düngemittel sowie Feinstverkapselungen in polymeren Stoffen. Im Rahmen der vorliegenden Erfindung ist es insbesondere bevorzugt, wenn die Verbindungen der allgemeinen Formel (I) in der Form einer Sprühformulieruing verwendet werden. Formulations are transferred, such as solutions, emulsions, wettable powders, water and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, scattering granules, suspension emulsion concentrates, drug-impregnated natural products, drug-impregnated synthetic substances, fertilizers and Very fine encapsulation in polymeric substances. In the context of the present invention it is particularly preferred if the compounds of the general formula (I) are used in the form of a spray formulation.
Die vorliegende Erfindung betrifft daher darüber hinaus auch eine Sprühformulierung zur Steigerung der Widerstandsfähigkeit von Pflanzen gegenüber abiotischem Stress. Im Folgenden wird eine Sprühformulierung näher beschrieben: Die Formulierungen zur Sprühapplikation werden in bekannter Weise hergestellt, z.B. durch Vermischen der erfindungsgemäßen Verbindungen der allgmeinen Formel (I) mit Streckmitteln, also flüssigen Lösungsmitteln und/oder festen Trägerstoffen, gegebenenfalls unter Verwendung von oberflächenaktiven Mitteln, also The present invention therefore further relates to a spray formulation for increasing the resistance of plants to abiotic stress. In the following, a spray formulation is described in more detail: The formulations for spray application are prepared in a known manner, for example by mixing the compounds of the general formula (I) according to the invention with extenders, ie liquid solvents and / or solid carriers, if appropriate using surface-active agents, ie
Emulgiermitteln und/oder Dispergiermitteln und/oder schaumerzeugenden Mitteln. Weitere übliche Zusatzstoffe, wie zum Beispiel übliche Streckmittel sowie Lösungsoder Verdünnungsmittel, Farbstoffe, Netzmittel, Dispergiermittel, Emulgatoren, Entschäumer, Konservierungsmittel, sekundäre Verdickungsmittel, Kleber,  Emulsifiers and / or dispersants and / or foam-forming agents. Other conventional additives, such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives,
Gibberelline und auch Wasser, können gegebenenfalls auch verwendet werden. Die Herstellung der Formulierungen erfolgt entweder in geeigneten Anlagen oder auch vor oder während der Anwendung. Gibberellins and also water may also be used if necessary. The preparation of the formulations is carried out either in suitable systems or before or during use.
Als Hilfsstoffe können solche Stoffe Verwendung finden, die geeignet sind, dem Mittel selbst oder und/oder davon abgeleitete Zubereitungen (z.B. Spritzbrühen) besondere Eigenschaften zu verleihen, wie bestimmte technische Eigenschaften und/oder auch besondere biologische Eigenschaften. Als typische Hilfsmittel kommen in Frage: Excipients which can be used are those which are suitable for imparting special properties to the composition itself or to preparations derived therefrom (for example spray mixtures), such as certain technical properties and / or special biological properties. As typical aids are:
Streckmittel, Lösemittel und Trägerstoffe. Als Streckmittel eignen sich z.B. Wasser, polare und unpolare organische chemische Flüssigkeiten z.B. aus den Klassen der aromatischen und nicht-aromatischen Extenders, solvents and carriers. As extender, e.g. Water, polar and non-polar organic chemical liquids e.g. from the classes of aromatic and non-aromatic
Kohlenwasserstoffe (wie Paraffine, Alkylbenzole, Alkylnaphthaline, Chlorbenzole), der Alkohole und Polyole (die ggf. auch substituiert, verethert und/oder verestert sein können), der Ketone (wie Aceton, Cyclohexanon), Ester (auch Fette und Öle) und (Poly-)Ether, der einfachen und substituierten Amine, Amide, Lactame (wie N-Hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which may also be substituted, etherified and / or esterified), ketones (such as acetone, cyclohexanone), esters (including fats and oils) and ( Poly) ethers, the simple and substituted amines, amides, lactams (such as
Alkylpyrrolidone) und Lactone, der Sulfone und Sulfoxide (wie Dimethylsysulfoxid). Alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as dimethyl sulfoxide).
Im Falle der Benutzung von Wasser als Streckmittel können z.B. auch organische Lösemittel als Hilfslösungsmittel verwendet werden. Als flüssige Lösemittel kommen im wesentlichen in Frage: Aromaten, wie Xylol, Toluol, oder Alkylnaphthaline, chlorierte Aromaten und chlorierte aliphatische Kohlenwasserstoffe, wie Chlorbenzole, Chlorethylene oder Methylenchlorid, aliphatische Kohlenwasserstoffe, wie Cyclohexan oder Paraffine, z.B. Erdölfraktionen, mineralische und pflanzliche Öle, Alkohole, wie Butanol oder Glykol sowie deren Ether und Ester, Ketone wie Aceton, Methylethyl- keton, Methyl isobutylketon oder Cyclohexanon, stark polare Lösungsmittel, wie In the case of using water as extender, for example, organic solvents can also be used as auxiliary solvents. Suitable liquid solvents are essentially: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methylethyl ketone, methyl isobutyl ketone or cyclohexanone, strong polar solvents, such as
Dimethylsulfoxid, sowie Wasser. Dimethyl sulfoxide, as well as water.
Es können Farbstoffe wie anorganische Pigmente, z.B. Eisenoxid, Titanoxid, Ferro- cyanblau und organische Farbstoffe, wie Alizarin-, Azo- und Metallphthalocyanin- farbstoffe und Spurennährstoffe wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink verwendet werden. Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
Als Netzmittel, die in den erfindungsgemäß verwendbaren Formulierungen enthalten sein können, kommen alle zur Formulierung von agrochemischen Wirkstoffen üblichen, die Benetzung fördernden Stoffe in Frage. Vorzugsweise verwendbar sind Alkylnaphthalin-Sulfonate, wie Diisopropyl- oder Diisobutylnaphthalin-Sulfonate. Suitable wetting agents which may be present in the formulations which can be used according to the invention are all wetting-promoting substances customary for the formulation of agrochemical active compounds. Preferably usable are alkylnaphthalene sulfonates such as diisopropyl or diisobutylnaphthalene sulfonates.
Als Dispergiermittel und/oder Emulgatoren, die in den erfindungsgemäß verwendbaren Formulierungen enthalten sein können, kommen alle zur Formulierung von agrochemischen Wirkstoffen üblichen nichtionischen, anionischen und kationischen Dispergiermittel in Betracht. Vorzugsweise verwendbar sind nichtionische oder anionische Dispergiermittel oder Gemische von nichtionischen oder anionischen Dispergiermitteln. Als geeignete nichtionische Dispergiermittel sind insbesondere Ethylenoxid- Propylenoxid-Blockpolymere, Alkylphenolpolyglykolether sowie Tristryrylphenol- polyglykolether und deren phosphatierte oder sulfatierte Derivate zu nennen. Geeignete anionische Dispergiermittel sind insbesondere Ligninsulfonate, Poly- acrylsäuresalze und Arylsulfonat-Formaldehydkondensate. Als Entschäumer können in den erfindungsgemäß verwendbaren Formulierungen alle zur Formulierung von agrochemischen Wirkstoffen üblichen schaumhemmenden Stoffe enthalten sein. Vorzugsweise verwendbar sind Silikonentschäumer und Magne- siumstearat. Als Konservierungsmittel können in den erfindungsgemäß verwendbaren Suitable dispersants and / or emulsifiers which may be present in the formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemical active compounds. Preferably usable are nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants. Particularly suitable nonionic dispersants are ethylene oxide-propylene oxide block polymers, alkylphenol polyglycol ethers and tristryrylphenol polyglycol ethers and their phosphated or sulfated derivatives. Suitable anionic dispersants are in particular lignosulfonates, polyacrylic acid salts and arylsulfonate-formaldehyde condensates. Defoamers which may be present in the formulations which can be used according to the invention are all foam-inhibiting substances customary for the formulation of agrochemical active compounds. Preference is given to using silicone defoamers and magnesium stearate. As preservatives can be used in the invention
Formulierungen alle für derartige Zwecke in agrochemischen Mitteln einsetzbaren Stoffe vorhanden sein. Beispielhaft genannt seien Dichlorophen und Benzylalkohol- hemiformal. Als sekundäre Verdickungsmittel, die in den erfindungsgemäß verwendbaren Formulierungen enthalten sein können, kommen alle für derartige Zwecke in agrochemischen Mitteln einsetzbaren Stoffe in Frage. Vorzugsweise in Betracht kommen Cellulose- derivate, Acrylsäurederivate, Xanthan, modifizierte Tone und hochdisperse Kiesel- säure. Formulations all substances that can be used for such purposes in agrochemical agents be present. Examples include dichlorophen and benzyl alcohol hemiformal. Suitable secondary thickeners which may be present in the formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Preference is given to cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silicic acid.
Als Kleber, die in den erfindungsgemäß verwendbaren Formulierungen enthalten sein können, kommen alle üblichen in Beizmitteln einsetzbaren Bindemittel in Frage. Suitable adhesives which may be present in the formulations which can be used according to the invention are all customary binders which can be used in pickling agents.
Vorzugsweise genannt seien Polyvinylpyrrolidon, Polyvinylacetat, Polyvinylalkohol und Tylose. Als Gibberelline, die in den erfindungsgemäß verwendbaren Formulierungen enthalten sein können, kommen vorzugsweise die Gibberelline A1 , A3 (= Preferably mentioned are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and Tylose. As gibberellins which may be present in the formulations which can be used according to the invention, the gibberellins A1, A3 (=
Gibberellinsäure), A4 und A7 infrage, besonders bevorzugt verwendet man die Gibberellinic acid), A4 and A7 in question, particularly preferably using the
Gibberellinsäure. Die Gibberelline sind bekannt (vgl. R. Wegler„Chemie der Gibberellic acid. The gibberellins are known (see R. Wegler "Chemie der
Pflanzenschutz- und Schädlingsbekämpfungsmittel", Bd. 2, Springer Verlag, 1970, S. 401 -412). Phytosanitary and Pesticides ", Vol. 2, Springer Verlag, 1970, pp. 401-412).
Weitere Additive können Duftstoffe, mineralische oder vegetabilische gegebenenfalls modifizierte Öle, Wachse und Nährstoffe (auch Spurennährstoffe), wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink sein. Weiterhin enthalten sein können Stabilisatoren wie Kältestabilisatoren, Oxidationsschutzmittel, Lichtschutzmittel oder andere die chemische und / oder physikalische Stabilität verbessernde Mittel. Other additives may be fragrances, mineral or vegetable optionally modified oils, waxes and nutrients (also micronutrients), such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc. Stabilizers such as cold stabilizers, antioxidants, light stabilizers or other chemical and / or physical stability improving agents may also be included.
Die Formulierungen enthalten im Allgemeinen zwischen 0,01 und 98 Gew.-%, vorzugsweise zwischen 0,5 und 90 %, der Verbindung der allgemeinen Formel (I). The formulations generally contain between 0.01 and 98% by weight, preferably between 0.5 and 90%, of the compound of general formula (I).
Die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) können in The compounds of general formula (I) according to the invention can be described in
handelsüblichen Formulierungen sowie in den aus diesen Formulierungen bereiteten Anwendungsformen in Mischung mit anderen Wirkstoffen wie Insektiziden, commercial formulations and in the formulations prepared from these formulations in admixture with other active ingredients such as insecticides,
Lockstoffen, Sterilantien, Bakteriziden, Akariziden, Nematiziden, Fungiziden, wachstumsregulierenden Stoffen, Herbiziden, Safenern, Düngemitteln oder Attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, safeners, fertilizers or
Semiochemicals vorliegen. Ferner lässt sich die beschriebene positive Wirkung der Verbindungen der Formel (I) auf die pflanzeneigenen Abwehrkräfte durch eine zusätzliche Behandlung mit insektziden, fungiziden oder bakteriziden Wirkstoffen unterstützen. Bevorzugte Zeitpunkte für die Applikation der erfindungsgemäß zu verwendenden Verbindungen der allgemeinen Formel (I) oder deren Salze zur Steigerung der Resistenz gegenüber abiotischem Stress sind Boden-, Stamm- und/oder Semiochemicals are present. Furthermore, the described positive effect of the compounds of the formula (I) on the plant's own defenses can be assisted by additional treatment with insecticidal, fungicidal or bactericidal active substances. Preferred times for the application of the compounds of the general formula (I) to be used according to the invention or their salts for increasing the resistance to abiotic stress are soil, parent and / or
Blattbehandlungen mit den zugelassenen Aufwandmengen. Die erfindungsgemäßen Wirkstoffe der allgemeinen Formel (I) oder deren Salze können im Allgemeinen darüber hinaus in ihren handelsüblichen Formulierungen sowie in den aus diesen Formulierungen bereiteten Anwendungsformen in Leaf treatments with the approved application rates. The active compounds of the general formula (I) or salts thereof according to the invention can generally also be used in their commercial formulations and in the forms of use prepared from these formulations
Mischungen mit anderen Wirkstoffen, wie Insektiziden, Lockstoffen, Sterilantien, Akariziden, Nematiziden, Fungiziden, Bakteriziden, wachstumsregulierenden Stoffen, die Pflanzenreife beeinflussenden Stoffen, Safenern oder Herbiziden vorliegen. Mixtures with other active ingredients, such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, bactericides, growth regulators, plant maturity affecting substances, safeners or herbicides are present.
Die Erfindung soll durch die nachfolgenden biologischen Beispiele veranschaulicht werden, ohne sie jedoch darauf einzuschränken. Biologische Beispiele: The invention will be illustrated by the following biological examples without, however, limiting them thereto. Biological examples:
In vivo-Analysen In vivo analyzes
Samen von mono- bzw. dikotylen Kulturpflanzen wurden in Holzfaser- oder Seeds of monocotyledonous or dicotyledonous crops were found in wood fiber or
Plastiktöpfen in sandigem Lehmboden ausgesät, mit Erde oder Sand abgedeckt und im Gewächshaus unter guten Wachstumsbedingungen angezogen. Die Behandlung der Versuchspflanzen erfolgte im frühen Laubblattstadium (BBCH10 - BBCH13). Zur Gewährleistung einer uniformen Wasserversorgung vor Stressbeginn wurden die bepflanzten Töpfe vor Substanzapplikation durch Anstaubewässerung mit Wasser versorgt. Seeded plastic pots in sandy loam soil, covered with soil or sand and grown in the greenhouse under good growth conditions. The treatment of the test plants took place in the early leaf foliage stage (BBCH10 - BBCH13). To ensure a uniform water supply before the onset of stress, the planted pots were supplied with water before being applied with substance by means of dewatering.
Die in Form von benetzbaren Pulvern (WP) formulierten erfindungsgemässen The formulated according to the invention in the form of wettable powders (WP)
Verbindungen wurden als wässrige Suspension mit einer Wasseraufwandmenge von umgerechnet 600 l/ha unter Zusatz von 0,2% Netzmittel (z.B. Agrotin) auf die grünen Pflanzenteile gesprüht. Unmittelbar nach Substanzapplikation erfolgte die Stressbehandlung der Pflanzen. Die Holzfasertöpfe wurden dazu in Plastikeinsätze transferiert, um anschliessendes, zu schnelles Abtrocknen zu verhindern. Der Trockenstress wurde durch langsames Abtrocknen unter folgenden Bedingungen induziert: Compounds were added to the green as an aqueous suspension with a water application rate of 600 l / ha with the addition of 0.2% wetting agent (eg agrotin) Sprayed plant parts. Immediately after substance administration, the stress treatment of the plants was carried out. The wood fiber pots were transferred to plastic inserts to prevent subsequent, too rapid drying. The dry stress was induced by slow drying under the following conditions:
„Tag": 14 Stunden beleuchtet bei ~ 26-30°C "Day": 14 hours lit at ~ 26-30 ° C
„Nacht": 10 Stunden ohne Beleuchtung bei ~ 18-20°C. Die Dauer der jeweiligen Stressphasen richtete sich hauptsächlich nach dem Zustand der gestressten Kontrollpflanzen. Sie wurde (durch Wiederbewässerung und Transfer in ein Gewächshaus mit guten Wachstumsbedingungen) beendet, sobald irreversible Schäden an den gestressten Kontrollpflanzen zu beobachten waren. Nach Beendigung der Stressphase folgte eine ca. 4-7 tägige Erholungsphase, während der die Pflanzen abermals unter guten Wachstumsbedingungen im "Night": 10 hours without illumination at ~ 18-20 ° C. The duration of the respective stress phases mainly depends on the condition of the stressed control plants and was terminated (by irrigation and transfer to a greenhouse with good growth conditions), as soon as irreversible damage occurs After completion of the stress phase, a recovery period of about 4-7 days followed, during which the plants were again grown under good growth conditions
Gewächshaus gehalten wurden. Die Dauer der Erholungsphase richtete sich hauptsächlich danach, wann die Versuchspflanzen einen Zustand erreicht hatten, der eine visuelle Bonitur potenzieller Effekte ermöglichte, und ist daher variabel. Greenhouse were kept. The duration of the recovery period was mainly dependent on when the test plants reached a state that allowed a visual assessment of potential effects and is therefore variable.
Wenn dieser Zeitpunkt erreicht war, wurden die Schadintensitäten visuell im Vergleich zu unbehandelten, ungestressten Kontrollen gleichen Alters bonitiert. Die Erfassung der Schadintensität erfolgte zunächst in Prozent. Aus diesen Werten wurde sodann der Wirkungsgrad der Testverbindungen nach folgender Formel ermittelt: When this time was reached, the levels of damage were scored visually compared to untreated, unstressed controls of the same age. The detection of the damage intensity was initially in percent. From these values, the efficiency of the test compounds was then determined according to the following formula:
S  S
WG: Wirkungsgrad (Efficacy) WG: Efficiency
Sls: Schadintensität der gestressten Kontrollpflanzen Sl s : Harmful intensity of stressed control plants
S : Schadintensität der mit Testverbindung behandelten, gestressten Pflanzen Bei den in unten stehenden Tabellen A-1 bis A-3 angegebenen Werten handelt es sich um Mittelwerte aus mindestens einem Versuch mit mindestens zwei Replikaten. S: Detrimental intensity of the test compound treated, stressed plants The values given in Tables A-1 to A-3 below are average values from at least one test with at least two replicates.
Gemessen wurden die.Wirkungen ausgewählter Verbindungen der allgemeinen Formel (I) unter Trockenstress auf verschiedene Kulturpflanzen The effects of selected compounds of the general formula (I) under dry stress on various crop plants were measured
Tabelle A-1 Table A-1
Tabelle A-2 Table A-2
WG [%]  WG [%]
No. Substanz Dosierung Einheit  No. Substance dosage unit
(ZEAMX)  (ZEAMX)
1 A5-30 25 g/ha > 5 %  1 A5-30 25 g / ha> 5%
2 A6-21 250 g/ha > 5 %  2 A6-21 250 g / ha> 5%
3 B2-1 25 g/ha > 5 %  3 B2-1 25 g / ha> 5%
4 B2-21 250 g/ha > 5 %  4 B2-21 250 g / ha> 5%
5 B2-61 250 g/ha > 5 %  5 B2-61 250 g / ha> 5%
6 C1 -61 250 g/ha > 5 % 6 C1 -61 250 g / ha> 5%
Tabelle A-3 Table A-3
/n vivo-Analysen - Teil B / n vivo Analyzes - Part B
Sannen von mono- bzw. dikotylen Kulturpflanzen wurden in Plastiktöpfen in sandigem Lehmboden ausgesät, mit Erde oder Sand abgedeckt und im Gewächshaus unter guten Wachstumsbedingungen angezogen. Die Behandlung der Versuchspflanzen erfolgt im frühen Laubblattstadium (BBCH10 - BBCH13). Zur Gewährleistung einer uniformen Wasserversorgung vor Stressbeginn wurden die bepflanzten Töpfe vor Substanzapplikation durch Anstaubewässerung mit Wasser versorgt. Sannen of monocotyledonous or dicotyledonous crops were sown in sandy loam soil in plastic pots, covered with soil or sand and grown in the greenhouse under good growth conditions. The treatment of the test plants takes place in the early leaves leaf stage (BBCH10 - BBCH13). To ensure a uniform water supply before the onset of stress, the planted pots were supplied with water before being applied with substance by means of dewatering.
Die erfindungsgemässen Verbindungen wurden zunächst als benetzbare Pulver (WP) formuliert oder in einem Lösungsmittelgemisch gelöst. Die weitere Verdünnung erfolgte mit Wasser unter Zusatz von 0,2% Netzmittel (z.B. Agrotin). Die fertigeThe compounds according to the invention were initially formulated as wettable powders (WP) or dissolved in a solvent mixture. Further dilution was made with water with the addition of 0.2% wetting agent (e.g., agrotine). The finished one
Spritzbrühe wurde mit einer Wasseraufwandmenge von umgerechnet 600 l/ha auf die grünen Pflanzenteile gesprüht. Unmittelbar nach Substanzapplikation erfolgte die Stressbehandlung der Pflanzen. Der Trockenstress wurde durch langsames Abtrocknen unter folgenden Bedingungen induziert: Spray mixture was sprayed onto the green parts of the plant at a rate of 600 l / ha. Immediately after administration of the substance, stress treatment of the plants took place. The dry stress was induced by slow drying under the following conditions:
„Tag": 14 Stunden beleuchtet bei ~ 26-30°C "Day": 14 hours lit at ~ 26-30 ° C
„Nacht": 10 Stunden ohne Beleuchtung bei ~ 18-20°C. Die Dauer der jeweiligen Stressphasen richtete sich hauptsächlich nach dem Zustand der gestressten Kontrollpflanzen. Sie wurde (durch Wiederbewässerung und Transfer in ein Gewächshaus mit guten Wachstumsbedingungen) beendet, sobald irreversible Schäden an den gestressten Kontrollpflanzen zu beobachten waren. Nach Beendigung der Stressphase folgte eine ca. 4-7 tägige Erholungsphase, während der die Pflanzen abermals unter guten Wachstumsbedingungen im "Night": 10 hours without illumination at ~ 18-20 ° C. The duration of the respective stress phases mainly depends on the condition of the stressed control plants and was terminated (by irrigation and transfer to a greenhouse with good growth conditions), as soon as irreversible damage occurs on the stressed control plants. After completion of the stress phase followed by a 4-7 day recovery period during which the plants again under good growth conditions in
Gewächshaus gehalten wurden. Die Dauer der Erholungsphase richtete sich Greenhouse were kept. The duration of the recovery phase was directed
hauptsächlich danach, wann die Versuchspflanzen einen Zustand erreicht hatten, der eine visuelle Bonitur potenzieller Effekte ermöglichte, und war daher variabel. mainly after when the experimental plants reached a state that allowed a visual assessment of potential effects, and was therefore variable.
Wenn dieser Zeitpunkt erreicht war, wurde das Erscheinungsbild der mit When that time was reached, the appearance of the
Testsubstanzen behandelten Pflanzen im Vergleich zu den gestressten Test substances treated plants compared to the stressed ones
Kontrollpflanzen nach folgenden Kategorien erfasst: kein positiver Effekt Control plants included in the following categories: no positive effect
leicht positiver Effekt  slightly positive effect
deutlich positiver Effekt  clearly positive effect
stark positiver Effekt  strong positive effect
Um auszuschliessen, dass die beobachteten Effekte von der ggf. fungiziden oder Insektiziden Wirkung der Testverbindungen beeinflusst wurden, wurde zudem darauf geachtet, dass die Versuche ohne Pilzinfektion oder Insektenbefall abliefen. In order to rule out that the observed effects were influenced by the possibly fungicidal or insecticidal activity of the test compounds, care was also taken that the experiments proceeded without fungus infection or insect infestation.
Bei den in den unten stehenden Tabellen B-1 und B-2 angegebenen Werten handelt es sich um Mittelwerte der Ergebnisse aus mindestens drei Replikaten. The values given in Tables B-1 and B-2 below are averages of the results from at least three replicates.
Wirkungen ausgewählter Verbindungen der allgemeinen Formel (I) unter Effects of selected compounds of general formula (I) under
Trockenstress gemäß nachstehender Tabellen B-1 und B-2: Drought stress according to Tables B-1 and B-2 below:
Tabelle B-1 Table B-1
Effekt  effect
No. Substanz Dosierung Einheit  No. Substance dosage unit
(BRSNS)  (BRSNS)
1 A1 -15 25 g/ha ++  1 A1 -15 25 g / ha ++
2 A2-61 25 g/ha ++  2 A2-61 25 g / ha ++
3 A13-1 250 g/ha ++  3 A13-1 250 g / ha ++
4 A20-1 250 g/ha + A22-1 250 g/ha +4 A20-1 250 g / ha + A22-1 250 g / ha +
A24-40 250 g/ha +A24-40 250 g / ha +
B3-40 250 g/ha +B3-40 250 g / ha +
D1-1 25 g/ha +D1-1 25 g / ha +
D2-21 25 g/ha +D2-21 25 g / ha +
D6-1 25 g/ha +D6-1 25g / ha +
D6-4 25 g/ha +D6-4 25 g / ha +
D6-11 250 g/ha +D6-11 250 g / ha +
D6-61 250 g/ha +D6-61 250 g / ha +
E1-4 250 g/ha +E1-4 250 g / ha +
E2-61 250 g/ha +E2-61 250 g / ha +
F1-4 250 g/ha +F1-4 250 g / ha +
F1-94 250 g/ha +F1-94 250 g / ha +
F2-4 250 g/ha +F2-4 250 g / ha +
F2-40 250 g/ha +F2-40 250 g / ha +
F2-61 250 g/ha +F2-61 250 g / ha +
G1-2 25 g/ha +G1-2 25 g / ha +
G8-1 250 g/ha +G8-1 250 g / ha +
G8-11 25 g/ha +G8-11 25g / ha +
G8-94 25 g/ha +G8-94 25 g / ha +
G9-4 250 g/ha ++G9-4 250 g / ha ++
G9-11 250 g/ha +G9-11 250 g / ha +
G9-21 250 g/ha ++G9-21 250 g / ha ++
G9-36 250 g/ha ++G9-36 250 g / ha ++
G10-4 250 g/ha +G10-4 250 g / ha +
G 10-94 250 g/ha ++G 10-94 250 g / ha ++
G11-4 250 g/ha ++G11-4 250 g / ha ++
G11-94 250 g/ha +G11-94 250 g / ha +
H1-3 25 g/ha +H1-3 25 g / ha +
H1-11 250 g/ha +H1-11 250 g / ha +
H1-21 25 g/ha +H1-21 25 g / ha +
H2-4 250 g/ha + 37 H2-1 1 25 g/ha + H2-4 250 g / ha + 37 H2-1 1 25 g / ha +
38 H2-36 250 g/ha ++ 38 H2-36 250 g / ha ++
39 H2-94 250 g/ha + 39 H2-94 250 g / ha +
Tabelle B-2 Table B-2
Effekt effect
No. Substanz Dosierung Einheit No. Substance dosage unit
(TRZAS) (TRZAS)
1 A1 -15 25 g/ha + 1 A1 -15 25 g / ha +
2 A2-61 25 g/ha + 2 A2-61 25 g / ha +
3 A4-4 25 g/ha +3 A4-4 25 g / ha +
4 A4-61 25 g/ha +4 A4-61 25 g / ha +
5 A7-61 250 g/ha ++5 A7-61 250 g / ha ++
6 A8-1 25 g/ha +6 A8-1 25 g / ha +
7 A13-5 25 g/ha +7 A13-5 25 g / ha +
8 A14-1 25 g/ha +8 A14-1 25 g / ha +
9 A14-615 25 g/ha +9 A14-615 25 g / ha +
10 A18-61 25 g/ha + 10 A18-61 25 g / ha +
1 1 A20-61 250 g/ha +  1 1 A20-61 250 g / ha +
12 A22-1 250 g/ha +  12 A22-1 250 g / ha +
13 A24-40 250 g/ha +  13 A24-40 250 g / ha +
14 A24-679 250 g/ha +  14 A24-679 250 g / ha +
15 B3-21 25 g/ha +  15 B3-21 25 g / ha +
16 B3-61 250 g/ha +  16 B3-61 250 g / ha +
17 B4-1 25 g/ha +  17 B4-1 25 g / ha +
18 B4-21 25 g/ha +  18 B4-21 25 g / ha +
19 B4-61 25 g/ha +  19 B4-61 25 g / ha +
20 C3-61 250 g/ha + 20 C3-61 250 g / ha +
21 D1 -1 250 g/ha +21 D1 -1 250 g / ha +
22 D1 -4 250 g/ha +22 D1 -4 250 g / ha +
23 D1 -61 25 g/ha +23 D1 -61 25 g / ha +
24 D2-61 25 g/ha +24 D2-61 25 g / ha +
25 D6-4 25 g/ha + D6-11 25 g/ha +25 D6-4 25 g / ha + D6-11 25g / ha +
D6-21 250 g/ha +D6-21 250 g / ha +
D6-36 250 g/ha +D6-36 250 g / ha +
D6-61 25 g/ha +D6-61 25 g / ha +
D6-94 250 g/ha +D6-94 250 g / ha +
E1-1 250 g/ha +E1-1 250 g / ha +
E1-3 250 g/ha +E1-3 250 g / ha +
E1-61 250 g/ha +E1-61 250 g / ha +
E1-94 25 g/ha +E1-94 25 g / ha +
E1-351 25 g/ha +E1-351 25 g / ha +
E5-61 25 g/ha +E5-61 25 g / ha +
F1-4 250 g/ha +F1-4 250 g / ha +
F1-61 250 g/ha +F1-61 250 g / ha +
F2-1 250 g/ha +F2-1 250 g / ha +
F2-61 250 g/ha +F2-61 250 g / ha +
F2-94 25 g/ha +F2-94 25 g / ha +
G1-1 25 g/ha +G1-1 25 g / ha +
G8-1 250 g/ha +G8-1 250 g / ha +
G8-21 250 g/ha +G8-21 250 g / ha +
G8-36 250 g/ha ++G8-36 250 g / ha ++
G8-94 25 g/ha ++G8-94 25 g / ha ++
G9-4 25 g/ha ++G9-4 25 g / ha ++
G9-11 250 g/ha +G9-11 250 g / ha +
G9-15 250 g/ha +G9-15 250 g / ha +
G9-21 250 g/ha +G9-21 250 g / ha +
G9-36 25 g/ha +G9-36 25 g / ha +
G9-94 250 g/ha ++G9-94 250 g / ha ++
G10-11 250 g/ha +G10-11 250 g / ha +
G10-21 25 g/ha +G10-21 25 g / ha +
G 10-36 250 g/ha ++G 10-36 250 g / ha ++
G10-61 250 g/ha +G10-61 250 g / ha +
G 10-94 25 g/ha + 58 G11-4 250 g/ha +G 10-94 25 g / ha + 58 G11-4 250 g / ha +
59 G11-36 250 g/ha ++59 G11-36 250 g / ha ++
60 G11-94 250 g/ha +60 G11-94 250 g / ha +
61 H1-3 25 g/ha +61 H1-3 25 g / ha +
62 H1-11 250 g/ha +62 H1-11 250 g / ha +
63 H2-1 250 g/ha +63 H2-1 250 g / ha +
64 H2-3 250 g/ha +64 H2-3 250 g / ha +
65 H2-4 250 g/ha +65 H2-4 250 g / ha +
66 H2-11 250 g/ha +66 H2-11 250 g / ha +
67 H2-15 25 g/ha ++67 H2-15 25 g / ha ++
68 H2-61 250 g/ha +68 H2-61 250 g / ha +
69 H2-94 250 g/ha + 69 H2-94 250 g / ha +
In den zuvorgenannten Tabellen bedeuten: In the aforementioned tables mean:
BRSNS = Brassica napus BRSNS = Brassica napus
ZEAMX = Zea mays ZEAMX = Zea mays
TRZAS = Triticum aestivunn  TRZAS = Triticum aestivunn

Claims

Patentansprüche BCS151027 Claims BCS151027
1 . Substituierte Heteroarylcarbonsaurehydrazide der allgenneinen Formel (I) oder deren Salze, 1 . Substituted heteroarylcarboxylic acid hydrazides of the general formula (I) or salts thereof,
worin wherein
R1, R2 und R7 unabhängig voneinander für Wasserstoff, Halogen, Cyano, Nitro, NR21R22, OR23, S(O)nR24, Thiocyanato, Isothiocyanato, (Ci-C8)-Alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (Ci-Cio)-Haloalkyl, (C2-C8)-Haloalkenyl, (C2-C8)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-Cio)-Halocycloalkyl, (C4-Cio) Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, Pentafluorthio, (Ci-Cs)-Alkoxy- (Ci-Cs)-haloalkyl, (Ci-C8)-Haloalkoxy-(Ci-C8)-haloalkyl, (Ci-C8)- Haloalkoxy-(Ci-C8)-alkyl, Aryl, Aryl-(Ci-C8)-alkyl, Heteroaryl, Heteroaryl- (Ci-Cs)-alkyl, (C3-C8)-Cycloalkyl-(Ci-C8)-alkyl, (C -Cio)-Cycloalkenyl- (Ci-Cs)-alkyl, Heterocyclyl, Heterocyclyl-(Ci-C8)-alkyl, (Ci-Cs)-Alkoxy- (Ci-Cs)-alkyl, (Ci -C8)-Al kylth io-(Ci -C8)-al kyl , (Ci-C8)-Haloalkylthio- (Ci-Cs)-alkyl, (Ci-C8)-Alkylcarbonyl-(Ci-C8)-alkyl, COOR23, CONR21R22, COR23 , -C=NOR23, R21R22N-(Ci-C8)-alkyl, R23OOC-(Ci-C8)-alkyl, Aryl- (Ci-C8)-alkinyl, Heteroaryl-(Ci-C8)-alkinyl, Heterocyclyl-(Ci-C8)-alkinyl, Tris-[(Ci-C8)-alkyl]silyl-(C2-C8)-alkinyl, Bis-[(Ci-C8)-alkyl](aryl)silyl-(C2-C8) alkinyl, Bis-aryl[(Ci-C8)-alkyl]silyl-(C2-C8)-alkinyl, (C3-C8)-Cycloalkyl- (C2-C8)-al kinyl , Aryl-(C2-C8)-al kenyl , Heteroaryl-(C2-C8)-al kenyl , R 1 , R 2 and R 7 independently of one another represent hydrogen, halogen, cyano, nitro, NR 21 R 22 , OR 23 , S (O) n R 24 , thiocyanato, isothiocyanato, (C 1 -C 8 ) -alkyl, (C 2 -C 8) alkenyl, (C 2 -C 8) -alkynyl, (Ci-Cio) -haloalkyl, (C 2 -C 8) -haloalkenyl, (C 2 -C 8) haloalkynyl, (C 3 - Cio) cycloalkyl, (C 3 -Cio) halocycloalkyl, (C 4 -Cio) cycloalkenyl, (C4 -Cio) -Halocycloalkenyl, pentafluorosulfanyl, (Ci-Cs) alkoxy (Ci-Cs) -haloalkyl, ( C 1 -C 8 ) -haloalkoxy- (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -haloalkoxy- (C 1 -C 8 ) -alkyl, aryl, aryl- (C 1 -C 8 ) -alkyl, heteroaryl, heteroaryl- (Ci-Cs) alkyl, (C 3 -C 8) -cycloalkyl- (Ci-C8) alkyl, (C -Cio) cycloalkenyl (Ci-Cs) alkyl, heterocyclyl, heterocyclyl ( Ci-C 8) alkyl, (Ci-Cs) alkoxy (Ci-Cs) alkyl, (Ci-C8) -alkyl kylth io- (Ci-C8) -alkyl, (Ci-C 8 ) Haloalkylthio (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylcarbonyl (C 1 -C 8 ) -alkyl, COOR 23 , CONR 21 R 22 , COR 23 , -C = NOR 23 , R 21 R 22 N- (Ci-C 8) alkyl, R 23 OOC- (Ci-C 8) alkyl, aryl (Ci-C 8) alkynyl, heteroaryl (Ci-C 8 ) alkynyl, heterocyclyl (Ci-C8) -alkynyl, tris - [(Ci-C 8) alkyl] silyl (C 2 -C 8) -alkynyl, - bis [(Ci-C 8) -alkyl ] (aryl) silyl (C 2 -C 8) alkynyl, bis-aryl [(Ci-C 8) alkyl] (C 2 -C 8) silyl -alkynyl, (C 3 -C 8) cycloalkyl (C 2 -C 8 ) -alkenyl, aryl- (C 2 -C 8 ) -alkenyl, heteroaryl- (C 2 -C 8 ) -alkenyl,
Heterocyclyl-(C2-C8)-al kenyl , (C3-C8)-Cycloal kyl-(C2-C8)-al kenyl , (Ci -C8)- Alkoxy-(Ci-C8)-alkoxy-(Ci-C8)-alkyl, (Ci-C8)-Alkylaminosulfonylamino, (C3-C8)-Cycloalkylaminosulfonylamino, Diazo, Aryldiazo, Tris-[(Ci-C8)- alkyl]silyl, Bis-[(Ci-C8)-alkyl](aryl)silyl, Bis-aryl[(Ci-C8)-alkyl]silyl stehen, X1 , X2 und X3 gleich oder verschieden sind und unabhängig voneinander für O (Sauerstoff), S (Schwefel), N (Stickstoff), die Gruppierung C-R2 oder die Gruppierung N-R20 stehen, wobei jedoch in keinem Fall ein O- und S- Atom benachbart sind und wobei in keinem Fall jeweils mehr als ein O- oder S-Atom im gebildeten 5-gliedrigen Ring enthalten ist, und wobei R2 in der Gruppierung C-R2 und R20 in der Gruppierung N-R20 jeweils gleiche oder verschiedene Bedeutungen gemäß der oben- oder nachstehenden Definitionen haben, Heterocyclyl (C 2 -C 8) -alkenyl, (C 3 -C 8) -Cycloal alkyl- (C 2 -C 8) -alkenyl, (Ci-C8) - alkoxy (Ci-C 8) alkoxy (Ci-C 8) alkyl, (Ci-C 8) -Alkylaminosulfonylamino, (C 3 -C 8) -Cycloalkylaminosulfonylamino, diazo, Aryldiazo, tris - [(Ci-C 8) - alkyl] silyl, bis - [(C 1 -C 8 ) -alkyl] (aryl) silyl, bis-aryl [(C 1 -C 8 ) -alkyl] silyl, X 1 , X 2 and X 3 are identical or different and independently of one another are O (oxygen), S (sulfur), N (nitrogen), the group CR 2 or the group NR 20 , but in no case is an O and S atom are adjacent and wherein in each case more than one O or S atom in the formed 5-membered ring is not contained, and wherein R 2 in the group CR 2 and R 20 in the grouping NR 20 are the same or have different meanings according to the above or below definitions,
W für O (Sauerstoff) oder S (Schwefel) steht, W is O (oxygen) or S (sulfur),
A1 , A2, A3, A4 und A5 gleich oder verschieden sind und unabhängig voneinander für N (Stickstoff) oder die Gruppierung C-R7 stehen, wobei jedoch in keinem Fall mehr als zwei N-Atome benachbart sind, und wobei R7 in der Gruppierung C-R7 jeweils gleiche oder verschiedene Bedeutungen gemäß der oben stehenden Definition hat, A 1 , A 2 , A 3 , A 4 and A 5 are the same or different and are independently N (nitrogen) or the group CR 7 , but in no case more than two N atoms are adjacent, and wherein R 7 in the group CR 7 has the same or different meanings as defined above,
R3 für (Ci-C8)-Alkyl, Cyano-(Ci-C8)-Alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (Ci-Cio)-Haloalkyl, (C2-C8)-Haloalkenyl, (C2-C8)-Haloalkinyl, (C3-C10)- Cycloalkyl, (C3-Cio)-Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C4-Cio)- Halocycloalkenyl, , Aryl, Aryl-(Ci-C8)-alkyl, Heteroaryl, Heteroaryl-(Ci-Cs)- alkyl, (C3-C8)-Cycloalkyl-(Ci-C8)-alkyl, Heterocyclyl, Heterocyclyl-(Ci-C8)- alkyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, (Ci-C8)-Alkylthio-(Ci-C8)-alkyl, (Ci-C8)- Haloalkoxy-(Ci-C8)-alkyl, (Ci-C8)-Haloalkylthio-(Ci-C8)-alkyl, R21 R22N- (C1 -C8)-al kyl , (C1 -C8)-Al koxy-(Ci -C8)-al koxy-(Ci -C8)-al kyl steht, R 3 is (Ci-C 8) -alkyl, cyano- (Ci-C 8) alkyl, (C 2 -C 8) alkenyl, (C 2 -C 8) -alkynyl, (Ci-Cio) -haloalkyl , (C 2 -C 8) -haloalkenyl, (C 2 -C 8) haloalkynyl, (C3-C10) - cycloalkyl, (C3-Cio) halocycloalkyl, (C 4 -Cio) cycloalkenyl, (C 4 - Cio) - halocycloalkenyl,, aryl, aryl- (C 1 -C 8 ) -alkyl, heteroaryl, heteroaryl- (C 1 -C 8 ) -alkyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 8 ) -alkyl, heterocyclyl , heterocyclyl (Ci-C8) - alkyl, (Ci-C 8) alkoxy (Ci-C 8) alkyl, (Ci-C8) alkylthio (Ci-C8) alkyl, (C -C 8) - haloalkoxy (Ci-C 8) alkyl, (Ci-C 8) -Haloalkylthio- (Ci-C 8) alkyl, R 21 R 22 N- (C 1 -C 8) -alkyl, (C 1 -C 8 ) -alkoxy (C 1 -C 8 ) -alkoxy (C 1 -C 8 ) -alkyl radical,
R4 für Wasserstoff, (Ci-Cs)-Alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (C1-C10)- Haloalkyl, (C2-C8)-Haloalkenyl, (C2-C8)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-Cio)-Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, Aryl, Aryl-(Ci-C8)-alkyl, Heteroaryl, Heteroaryl-(Ci-C8)-alkyl, (C3-C8)- Cycloalkyl-(Ci-C8)-alkyl, Heterocyclyl, Heterocyclyl-(Ci-C8)-alkyl, (Ci-C8)- Alkoxy-(Ci-C8)-alkyl, (Ci-C8)-Alkylthio-(Ci-C8)-alkyl, (Ci-Cs)-Haloalkoxy- (Ci-Cs)-alkyl, (Ci-C8)-Haloalkylthio-(Ci-C8)-alkyl, (Ci-Cs)-Alkylamino- (Ci-Cs)-alkyl, Bis-[(Ci-C8)-alkyl]amino-(Ci-C8)-alkyl, (C3-C8)- Cycloalkylamino-(Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkoxy-(Ci-C8)- alkyl, COR23, (Ci-C8)-Alkoxycarbonyl, (C2-C8)-Alkenyloxycarbonyl, (C2-C8)-Alkinyloxycarbonyl, Aryl-(Ci-C8)-alkoxycarbonyl, Heteroaryl- (Ci -C8)-al koxycarbonyl , (C3-C8)-Cycloal kyl-(Ci -C8)-al koxycarbonyl , CONR21 R22, SO2R24, Hydroxycarbonyl-(Ci-C8)-alkyl, (Ci-C8)- Al koxycarbonyl-(Ci -C8)-al kyl , (C2-C8)-Al kenyloxycarbonyl-(Ci -C8)-al kyl , (C2-C8)-Al kinyloxycarbonyl-(Ci -C8)-al kyl , Aryl-(Ci -C8)-al koxycarbonyl- (Ci-C8)-alkyl, Heteroaryl-(Ci-C8)-alkoxycarbonyl-(Ci-C8)-alkyl, R 4 is hydrogen, (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, (C 1 -C 10) -haloalkyl, (C 2 -C 8 ) -haloalkenyl , (C 2 -C 8 ) -haloalkynyl, (C 3 -C 10) -cycloalkyl, (C 3 -C 10) -halocycloalkyl, (C 4 -C 10) -cycloalkenyl, (C 4 -C 10) -halocycloalkenyl, aryl, aryl- (Ci-C 8) alkyl, heteroaryl, heteroaryl (Ci-C 8) alkyl, (C 3 -C 8) - cycloalkyl, (Ci-C 8) alkyl, heterocyclyl, heterocyclyl (Ci-C 8 ) alkyl, (Ci-C8) - alkoxy (Ci-C 8) alkyl, (Ci-C8) alkylthio (Ci-C8) alkyl, (Ci-Cs) haloalkoxy (C -Cs) -alkyl, (Ci-C 8 ) -haloalkylthio (Ci-C 8 ) -alkyl, (Ci-Cs) -Alkylamino- (Ci-Cs) -alkyl, bis - [(Ci-C 8 ) - alkyl] amino- (Ci-C 8) alkyl, (C 3 -C 8) - Cycloalkylamino (Ci-C 8) alkyl, (Ci-C 8) alkoxy (Ci-C 8) alkoxy (Ci-C 8) - alkyl, COR 23, (Ci-C8) alkoxycarbonyl, (C 2 -C 8) alkenyloxycarbonyl, (C2-C8) alkynyloxycarbonyl, aryl (Ci-C8) alkoxycarbonyl, heteroaryl- (Ci-C8) -al koxycarbonyl, (C3-C8) -Cycloal alkyl- (Ci-C8) -al koxycarbonyl, CONR 21 R 22, SO 2 R 24, hydroxycarbonyl (Ci-C 8) alkyl, (Ci-C 8) - Al koxycarbonyl- (Ci-C8) - al kyl, (C2-C8) -alkyl kenyloxycarbonyl- (Ci-C8) -alkyl, (C2-C8) -alkyl kinyloxycarbonyl- (Ci-C8) -alkyl, aryl (Ci-C8 ) -alkoxycarbonyl- (C 1 -C 8 ) -alkyl, heteroaryl- (C 1 -C 8 ) -alkoxycarbonyl- (C 1 -C 8 ) -alkyl,
Heterocyclyl-(Ci-C8)-alkoxycarbonyl-(Ci-C8)-alkyl, (Ci-Cs)-Alkylcarbonyl- (Ci-Cs)-alkyl, (Ci-C8)-Alkylsulfonyl-(Ci-C8)-alkyl, (Ci-C8)-Al kylsulfinyl- (Ci-Cs)-alkyl steht, Heterocyclyl (Ci-C8) alkoxycarbonyl (Ci-C 8) alkyl, (Ci-Cs) alkylcarbonyl (Ci-Cs) alkyl, (Ci-C8) alkylsulfonyl (Ci-C 8 ) -alkyl, (C 1 -C 8 ) -alkylsulfinyl- (C 1 -C 5) -alkyl,
R5 und R6 unabhängig voneinander für Wasserstoff, (Ci-Cs)-Alkyl, (C2-C8)-R 5 and R 6 independently of one another represent hydrogen, (C 1 -C 5) -alkyl, (C 2 -C 8 ) -
Alkenyl, (C2-C8)-Alkinyl, (Ci-Cio)-Haloalkyl, (C2-C8)-Haloalkenyl, (C2-C8) Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-Cio)-Halocycloalkyl, (C -Cio)- Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, Aryl, Aryl-(Ci-C8)-alkyl, Alkenyl, (C 2 -C 8 ) alkynyl, (C 1 -C 8 ) haloalkyl, (C 2 -C 8 ) haloalkenyl, (C 2 -C 8 ) haloalkynyl, (C 3 -C 10) cycloalkyl, (C 3- Cio) -halocycloalkyl, (C -Cio) -cycloalkenyl, (C 4 -C 10) -halocycloalkenyl, aryl, aryl- (C 1 -C 8 ) -alkyl,
Heteroaryl, Heteroaryl-(Ci-C8)-alkyl, (C3-C8)-Cycloalkyl-(Ci-C8)-alkyl, Heterocyclyl , Heterocyclyl-(Ci -C8)-al kyl , (C1 -C8)-Al koxy-(Ci -C8)-al kyl , (C 1 -C8)-Al ky Ith io-(C 1 -C8)-al ky I , (Ci-C8)-Haloalkoxy-(Ci-C8)-alkyl, (Ci-C8)- Haloalkylthio-(Ci-C8)-alkyl, COOR23, CONR21 R22, Hydroxycarbonyl- (Ci-Cs)-alkyl, (Ci-C8)-Alkoxycarbonyl-(Ci-C8)-alkyl, (C2-C8)- Al kenyloxycarbonyl-(Ci -C8)-al kyl , (C2-C8)-Al kinyloxycarbonyl-(Ci -C8)- alkyl, Aryl-(Ci-C8)-alkoxycarbonyl-(Ci-C8)-alkyl, Heteroaryl-(Ci-Cs)- alkoxycarbonyl-(Ci-C8)-alkyl, Heterocyclyl-(Ci-C8)-alkoxycarbonyl- (Ci-C8)-alkyl stehen, Heteroaryl, heteroaryl (Ci-C 8) alkyl, (C 3 -C 8) -cycloalkyl- (Ci-C 8) alkyl, heterocyclyl, heterocyclyl (Ci-C8) -alkyl, (C 1 -C 8 ) -Al koxy- (Ci -C 8 ) -alkenyl, (C 1 -C 8 ) -Al ky Ith io- (C 1 -C 8 ) -alkenyl, (Ci-C 8 ) -haloalkoxy- (Ci-C 8) alkyl, (Ci-C 8) - Haloalkylthio- (Ci-C 8) alkyl, COOR 23, CONR 21 R 22, hydroxycarbonyl (Ci-Cs) alkyl, (Ci-C 8 ) alkoxycarbonyl (Ci-C 8) alkyl, (C 2 -C 8) - Al kenyloxycarbonyl- (Ci-C8) -alkyl, (C2-C8) -alkyl kinyloxycarbonyl- (Ci-C8) alkyl, aryl- (C 1 -C 8 ) -alkoxycarbonyl- (C 1 -C 8 ) -alkyl, heteroaryl- (C 1 -C 5 ) -alkoxycarbonyl- (C 1 -C 8 ) -alkyl, heterocyclyl- (C 1 -C 8 ) alkoxycarbonyl- (C 1 -C 8 ) -alkyl,
R3 und R4 mit dem Stickstoffatom, an das sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfall durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3-7-gliedrigen Ring bilden, R 3 and R 4 with the nitrogen atom to which they are attached form a completely saturated, partially saturated or completely unsaturated, optionally interrupted by heteroatoms and optionally further substituted 3-7-membered ring,
R1 und X1 , wenn X1 für eine Gruppe C-R2 steht, mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden, R 1 and X 1 , when X 1 is a group CR 2 , with the atoms to which they are attached, a fully saturated, partially saturated or fully unsaturated, optionally by heteroatoms form interrupted and optionally further substituted 5-7 membered ring,
X1 und X2, wenn beide für eine Gruppe C-R2 stehen, mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfalls durch Heteroatome X 1 and X 2 , when both represent a group CR 2 , with the atoms to which they are attached, a fully saturated, partially saturated or fully unsaturated, optionally by heteroatoms
unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden, A1 und A2, wenn beide für eine Gruppe C-R7 stehen, mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfalls durch Heteroatome form interrupted and optionally further substituted 5-7 membered ring, A 1 and A 2 , when both represent a group CR 7 , with the atoms to which they are attached, a fully saturated, partially saturated or fully unsaturated, optionally by heteroatoms
unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden,  form interrupted and optionally further substituted 5-7 membered ring,
A2 und A3, wenn beide für eine Gruppe C-R7 stehen, mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfalls durch Heteroatome A 2 and A 3 , when both represent a group CR 7 , with the atoms to which they are attached, a fully saturated, partially saturated or fully unsaturated, optionally by heteroatoms
unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden und  form interrupted and optionally further substituted 5-7 membered ring and
A3 und A4, wenn beide für eine Gruppe C-R7 stehen, mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfalls durch Heteroatome A 3 and A 4 , when both represent a group CR 7 , with the atoms to which they are attached, a fully saturated, partially saturated or fully unsaturated, optionally by heteroatoms
unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen interrupted and optionally further substituted 5-7 membered
Ring bilden, Form ring,
Y für eine Bindung oder für die Gruppierungen Y-1 bis Y-7 Y for a bond or for the groupings Y-1 to Y-7
steht, wobei R8, R9, R10, R1 1, R12, R13, R14, R15, R16, R17, R18 und R19 jeweils die Bedeutung gemäß der nachstehenden Definition haben und wobei der Pfeil für eine Bindung zum 6-gliedrigen Ring mit den , wherein R 8, R 9, R 10, R 1 1, R 12, R 13, R 14, R 15, R 16, R 17, R 18 and R 19 each have the meaning as defined below, and wherein the Arrow for a bond to the 6-membered ring with the
Gruppierungen A1, A2, A3, A4 und A5 steht, Groups A 1 , A 2 , A 3 , A 4 and A 5 ,
R8, R9, R10, R1 1, R12, R13, R14, R15, R16, R17, R18 und R19 unabhängig R 8, R 9, R 10, R 1 1, R 12, R 13, R 14, R 15, R 16, R 17, R 18 and R 19 are independently
voneinander für Wasserstoff, Halogen, (Ci-C8)-Alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (Ci-Cio)-Haloalkyl, (C2-C8)-Haloalkenyl, (C2-C8)- Haloalkinyl, (C3-Cio)-Cycloalkyl, Aryl, Aryl-(Ci-C8)-alkyl, Heteroaryl, Heteroaryl-(Ci-C8)-alkyl, (C3-C8)-Cycloalkyl-(Ci-C8)-alkyl, Heterocyclyl, Heterocyclyl-(Ci -C8)-al kyl , (Ci -C8)-Al koxy-(Ci -C8)-al kyl , (Ci -C8)-Al kylth io- (Ci-Cs)-alkyl, (Ci-C8)-Haloalkoxy-(Ci-C8)-alkyl, (Ci-Cs)-Haloalkylthio- (Ci-Cs)-alkyl, COOR23 stehen, each other is hydrogen, halogen, (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, (C 1 -C 10) -haloalkyl, (C 2 -C 8 ) -haloalkenyl, (C 2 -C 8 ) - haloalkynyl, (C 3 -C 10) -cycloalkyl, aryl, aryl- (C 1 -C 8 ) -alkyl, heteroaryl, heteroaryl- (C 1 -C 8 ) -alkyl, (C 3 -C 8 ) -cycloalkyl- (Ci-C 8 ) alkyl, heterocyclyl, heterocyclyl (Ci -C 8 ) -al kyl, (Ci -C 8 ) -Al koxy- (Ci -C 8 ) -al kyl, (Ci -C 8 ) -Al kylth io- (Ci-Cs) -alkyl, (Ci-C 8 ) -haloalkoxy- (Ci-C 8 ) -alkyl, (Ci-Cs) -haloalkylthio (Ci-Cs) -alkyl , COOR 23 ,
R5 und R6 mit dem Atom, an das sie gebunden sind, einen vollständig R 5 and R 6 with the atom to which they are attached, a complete
gesättigten, oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden,  form saturated, or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring,
R20 für Wasserstoff, (Ci-Cs)-Alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (C1-C10)- Haloalkyl, (C2-C8)-Haloalkenyl, (C2-C8)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C4-Cio)-Cycloalkenyl, (Ci-Cs)-Alkoxy, Aryl, Heteroaryl, Heterocyclyl, (Ci-Cs)-Alkylcarbonyl, Aryl-(Ci-C8)-Alkylcarbonyl, (C3-C8)- Cycloalkylcarbonyl, Arylcarbonyl, Heteroarylcarbonyl, (Ci-C8)- Alkoxycarbonyl, (C2-C8)-Alkenyloxycarbonyl, Aryl-(Ci-C8)-alkoxycarbonyl, Heteroaryl-(Ci-C8)-alkoxycarbonyl, (C3-C8)-Cycloalkyl-(Ci-C8)- alkoxycarbonyl, (Ci-C8)-Alkylsulfonyl, (Ci-C8)-Haloalkylsulfonyl, R 20 is hydrogen, (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, (C 1 -C 10) -haloalkyl, (C 2 -C 8 ) -haloalkenyl , (C 2 -C 8 ) -haloalkynyl, (C 3 -C 10) -cycloalkyl, (C 4 -C 10) -cycloalkenyl, (C 1 -C 8 ) -alkoxy, aryl, heteroaryl, heterocyclyl, (C 1 -C 8 ) -alkylcarbonyl , aryl (Ci-C8) alkylcarbonyl, (C 3 -C 8) - cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, (Ci-C8) - alkoxycarbonyl, (C 2 -C 8) alkenyloxycarbonyl, aryl (Ci- C 8 ) alkoxycarbonyl, Heteroaryl- (C 1 -C 8) -alkoxycarbonyl, (C 3 -C 8) -cycloalkyl- (C 1 -C 8) -alkoxycarbonyl, (C 1 -C 8) -alkylsulfonyl, (C 1 -C 8) -haloalkylsulfonyl,
Arylsulfonyl, Heteroarylsulfonyl, (C3-C8)-Cycloalkylsulfonyl, (Ci-Cs)- Alkylsulfinyl, Arylsulfinyl, Heteroarylsulfinyl, (C3-C8)-Cycloalkylsulfinyl steht, n für 0, 1 oder 2 steht  Arylsulfonyl, heteroarylsulfonyl, (C3-C8) -cycloalkylsulfonyl, (Ci-Cs) -alkylsulfinyl, arylsulfinyl, heteroarylsulfinyl, (C3-C8) -cycloalkylsulfinyl, n is 0, 1 or 2
R21 und R22 gleich oder verschieden sind und unabhängig voneinander für R 21 and R 22 are the same or different and independently of each other
Wasserstoff, (Ci-C8)-Alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (Ci-C8)- Cyanoalkyl, (Ci-Cio)-Haloalkyl, (C2-C8)-Haloalkenyl, (C2-C8)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-Cio)-Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C -Cio)-Halocycloalkenyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, (Ci-C8)- Haloalkoxy-(Ci-C8)-alkyl, (Ci -C8)-Al kylth io-(Ci -C8)-al kyl , (Ci-C8)- Haloalkylthio-(Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)-haloalkyl, Aryl, Aryl- (Ci-C8)-alkyl, Heteroaryl, Heteroaryl-(Ci-C8)-alkyl, (C3-C8)-Cycloalkyl- (Ci-C8)-alkyl, (C4-Cio)-Cycloalkenyl-(Ci-C8)-alkyl, COR23, SO2R24, Hydrogen, (Ci-C 8) alkyl, (C 2 -C 8) alkenyl, (C 2 -C 8) -alkynyl, (Ci-C 8) - cyanoalkyl, (Ci-Cio) -haloalkyl, (C 2 -C 8) -haloalkenyl, (C 2 -C 8) haloalkynyl, (C3-Cio) cycloalkyl, (C3-Cio) halocycloalkyl, (C 4 -Cio) cycloalkenyl, (C -Cio) -Halocycloalkenyl , (Ci-C 8) alkoxy (Ci-C 8) alkyl, (Ci-C 8) - haloalkoxy (Ci-C 8) alkyl, (Ci-C8) -alkyl kylth io- (C -C 8) -alkyl, (Ci-C 8) - Haloalkylthio- (Ci-C 8) alkyl, (Ci-C 8) alkoxy (Ci-C8) -haloalkyl, aryl, aryl (C C 8 ) alkyl, heteroaryl, heteroaryl (Ci-C 8 ) alkyl, (C 3 -C 8 ) cycloalkyl (Ci-C 8 ) alkyl, (C 4 -Cio) cycloalkenyl (Ci C 8 ) alkyl, COR 23 , SO 2 R 24 ,
(Ci-C8)-Alkyl-HNO2S-, (C3-C8)-Cycloalkyl-HNO2S-, Heterocyclyl, (Ci-C8)- Alkoxycarbonyl-(Ci-C8)-alkyl, (Ci-C8)-Alkoxycarbonyl, Aryl-(Ci-Cs)- Alkoxycarbonyl-(Ci-C8)-alkyl, Aryl-(Ci-C8)-Alkoxycarbonyl, Heteroaryl- (Ci-C8)-Alkoxycarbonyl, (C2-C8)-Alkenyloxycarbonyl, (C2-Cs)- Alkinyloxycarbonyl, Heterocyclyl-(Ci-C8)-alkyl stehen (Ci-C 8) -alkyl-HNO 2 S, (C 3 -C 8) cycloalkyl-HNO 2 S, heterocyclyl, (Ci-C8) - alkoxycarbonyl, (Ci-C8) alkyl, (C -C8) -alkoxycarbonyl, aryl- (C 1 -C 8) -alkoxycarbonyl- (C 1 -C 8) -alkyl, aryl- (C 1 -C 8) -alkoxycarbonyl, heteroaryl- (C 1 -C 8) -alkoxycarbonyl, (C 2 -C 8) Alkenyloxycarbonyl, (C 2 -Cs) -alkynyloxycarbonyl, heterocyclyl- (C 1 -C 8) -alkyl
R23 für Wasserstoff, (Ci-C8)-Alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (Ci-C8)- Cyanoalkyl, (Ci-Cio)-Haloalkyl, (C2-C8)-Haloalkenyl, (C2-C8)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-Cio)-Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C -Cio)-Halocycloalkenyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, (Ci-C8)-Alkoxy- (Ci-C8)-haloalkyl, Aryl, Aryl-(Ci-C8)-alkyl, Heteroaryl, Heteroaryl-(Ci-C8)- alkyl, (C3-C8)-Cycloalkyl-(Ci-C8)-alkyl, (C -Cio)-Cycloalkenyl-(Ci-C8)- al kyl , (Ci -Cs)-Al koxycarbonyl-(Ci -Cs)-al kyl , (C2-Cs)-Al kenyloxycarbonyl- (Ci -C8)-al kyl , Aryl-(Ci -Cs)-Al koxycarbonyl-(Ci -Cs)-al kyl , Hydroxycarbonyl- (Ci-C8)-alkyl, Heterocyclyl, Heterocyclyl-(Ci-C8)-alkyl steht und für Wasserstoff, (Ci-C8)-Alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (Ci-C8)- Cyanoalkyl, (Ci-Cio)-Haloalkyl, (C2-C8)-Haloalkenyl, (C2-C8)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-Cio)-Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C -Cio)-Halocycloalkenyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, (Ci-Cs)-Alkoxy- (Ci-Cs)-haloalkyl, Aryl, Aryl-(Ci-C8)-alkyl, Heteroaryl, Heteroaryl-(Ci-Cs)- al kyl , Heterocyclyl-(Ci -C8)-al kyl , (C3-C8)-Cycloal kyl-(Ci -C8)-al kyl , R 23 is hydrogen, (Ci-C 8) alkyl, (C 2 -C 8) alkenyl, (C 2 -C 8) -alkynyl, (Ci-C 8) - cyanoalkyl, (Ci-Cio) -haloalkyl , (C 2 -C 8) -haloalkenyl, (C 2 -C 8) haloalkynyl, (C3-Cio) cycloalkyl, (C3-Cio) halocycloalkyl, (C 4 -Cio) cycloalkenyl, (C -Cio ) -Halocycloalkenyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -haloalkyl, aryl, aryl- (C 1 -C 8 ) alkyl, heteroaryl, heteroaryl (Ci-C 8) - alkyl, (C3-C8) -cycloalkyl- (Ci-C8) alkyl, (C -Cio) cycloalkenyl (Ci-C 8) - al kyl, (C 1 -C 6) -alkoxycarbonyl- (C 1 -C 6) -alkyl, (C 2 -Cs) -alkhenyloxycarbonyl- (C 1 -C 8) -alkyl, aryl- (C 1 -C 6) -alkoxycarbonyl- (C 1 -C 8) -alkyl, hydroxycarbonyl- (C 1 -C 8) -alkyl, heterocyclyl, heterocyclyl- (C 1 -C 8) -alkyl and is hydrogen, (Ci-C 8) alkyl, (C 2 -C 8) alkenyl, (C 2 -C 8) -alkynyl, (Ci-C 8) - cyanoalkyl, (Ci-Cio) -haloalkyl, ( C 2 -C 8) -haloalkenyl, (C 2 -C 8) haloalkynyl, (C3-Cio) cycloalkyl, (C3-Cio) halocycloalkyl, (C 4 -Cio) cycloalkenyl, (C -Cio) - Halocycloalkenyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -haloalkyl, aryl, aryl- (C 1 -C 8 ) -alkyl, heteroaryl , heteroaryl (Ci-Cs) - al kyl, heterocyclyl (Ci-C8) -alkyl, (C 3 -C 8) -Cycloal alkyl- (Ci-C8) -alkyl,
(C4-Cio)-Cycloalkenyl-(Ci-C8)-alkyl, NR21R22 steht. (C 4 -C 10) -cycloalkenyl- (C 1 -C 8 ) -alkyl, NR 21 R 22 .
Substituierte Heteroarylcarbonsäurehydrazide gemäß Anspruch 1 , Substituted heteroarylcarboxylic acid hydrazides according to claim 1,
wobei in which
R1, R2 und R7 unabhängig voneinander für Wasserstoff, Halogen, Cyano, Nitro, NR21R22, OR23, S(O)nR24, Thiocyanato, Isothiocyanato, (Ci-C7)-Alkyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (Ci-C7)-Haloalkyl, (C2-C7)-Haloalkenyl, (C2-C7)-Haloalkinyl, (C3-C7)-Cycloalkyl, (C3-C7)-Halocycloalkyl, (C -C7)- Cycloalkenyl, (C4-C7)-Halocycloalkenyl, Pentafluorthio, (Ci-C7)-Alkoxy- (Ci-C7)-haloalkyl, (Ci-C7)-Haloalkoxy-(Ci-C7)-haloalkyl, (Ci-C7)- Haloalkoxy-(Ci-C7)-alkyl, Aryl, Aryl-(Ci-C7)-alkyl, Heteroaryl, Heteroaryl- (Ci-C7)-alkyl, (C3-C7)-Cycloalkyl-(Ci-C7)-alkyl, (C -C7)-Cycloalkenyl- (Ci-C7)-alkyl, Heterocyclyl, Heterocyclyl-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy- (Ci-C7)-alkyl, (C 1 -C7)-Al ky Ith io-(C 1 -C7)-al ky I , (Ci-C7)-Haloalkylthio- (Ci-C7)-alkyl, (Ci-C7)-Alkylcarbonyl-(Ci-C7)-alkyl, COOR23, CONR21R22, COR23 , -C=NOR23, R21R22N-(Ci-C7)-alkyl, R23OOC-(Ci-C7)-alkyl, Aryl- (Ci-C7)-alkinyl, Heteroaryl-(Ci-C7)-alkinyl, Heterocyclyl-(Ci-C7)-alkinyl, Tris-[(Ci-C7)-alkyl]silyl-(C2-C7)-alkinyl, Bis-[(Ci-C7)-alkyl](aryl)silyl-(C2-C7)- alkinyl, Bis-aryl[(Ci-C7)-alkyl]silyl-(C2-C7)-alkinyl, (C3-C7)-Cycloalkyl- (C2-C7)-al kinyl , Aryl-(C2-C7)-al kenyl , Heteroaryl-(C2-C7)-al kenyl , R 1 , R 2 and R 7 independently of one another represent hydrogen, halogen, cyano, nitro, NR 21 R 22 , OR 23 , S (O) n R 24 , thiocyanato, isothiocyanato, (C 1 -C 7 ) -alkyl, (C 2 -C 7) alkenyl, (C 2 -C 7) alkynyl, (Ci-C7) haloalkyl, (C 2 -C 7) haloalkenyl, (C 2 -C 7) haloalkynyl, (C 3 -C 7) cycloalkyl, (C 3 -C 7) halocycloalkyl, (C-C7) - cycloalkenyl, (C 4 -C 7) -Halocycloalkenyl, pentafluorosulfanyl, (Ci-C7) alkoxy (Ci- C 7 ) -haloalkyl, (C 1 -C 7 ) -haloalkoxy- (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -haloalkoxy- (C 1 -C 7 ) -alkyl, aryl, aryl- (C 1 -C 4 ) -haloalkyl; 7 ) alkyl, heteroaryl, heteroaryl (Ci-C 7 ) alkyl, (C 3 -C 7 ) cycloalkyl (Ci-C 7 ) alkyl, (C -C 7 ) cycloalkenyl (Ci-C 7) alkyl, heterocyclyl, heterocyclyl (Ci-C7) alkyl, (Ci-C7) alkoxy (Ci-C7) alkyl, (C 1 -C 7) -alkyl ky Ith io- ( C 1 -C 7) -al ky I, (Ci-C 7) -Haloalkylthio- (Ci-C7) alkyl, (Ci-C 7) alkylcarbonyl (Ci-C7) alkyl, COOR 23, CONR 21 R 22 , COR 23 , -C = NOR 23 , R 21 R 22 N- (C 1 -C 7 ) -alkyl, R 23 OOC- (C 1 -C 7 ) -alkyl, aryl- (C 1 -C 7 ) -alki nyl, heteroaryl (Ci-C7) alkynyl, heterocyclyl (Ci-C7) alkynyl, tris - [(Ci-C 7) alkyl] silyl (C 2 -C 7) alkynyl, bis- [(Ci-C 7) alkyl] (aryl) silyl (C 2 -C 7) - alkynyl, bis-aryl [(Ci-C 7) alkyl] silyl (C 2 -C 7) alkynyl, (C 3 -C 7 ) -cycloalkyl- (C 2 -C 7 ) -alkenyl, aryl- (C 2 -C 7 ) -alkenyl, heteroaryl- (C 2 -C 7 ) -alkenyl,
Heterocyclyl-(C2-C7)-al kenyl , (C3-C7)-Cycloal kyl-(C2-C7)-al kenyl , (Ci -C7)- Alkoxy-(Ci-C7)-alkoxy-(Ci-C7)-alkyl, (Ci-C7)-Alkylaminosulfonylamino, (C3-C7)-Cycloalkylaminosulfonylamino, Diazo, Aryldiazo, Tris-[(Ci-C7)- alkyl]silyl, Bis-[(Ci-C7)-alkyl](aryl)silyl, Bis-aryl[(Ci-C7)-alkyl]silyl stehen, X1, X2 und X3 gleich oder verschieden sind und unabhängig voneinander für O (Sauerstoff), S (Schwefel), N (Stickstoff), die Gruppierung C-R2 oder die Gruppierung N-R20 stehen, wobei jedoch in keinem Fall ein O- und S- Atom benachbart sind und wobei in keinem Fall jeweils mehr als ein O- oder S-Atom im gebildeten 5-gliedrigen Ring enthalten ist, und wobei R2 in der Gruppierung C-R2 und R20 in der Gruppierung N-R20 jeweils gleiche oder verschiedene Bedeutungen gemäß der oben- oder nachstehenden Definitionen haben, Heterocyclyl (C 2 -C 7) -alkenyl, (C 3 -C 7) -Cycloal alkyl- (C 2 -C 7) -alkenyl, (Ci-C7) - alkoxy (Ci-C 7) alkoxy (Ci-C7) alkyl, (Ci-C 7) -Alkylaminosulfonylamino, (C 3 -C 7) -Cycloalkylaminosulfonylamino, diazo, Aryldiazo, tris - [(Ci-C7) - alkyl] silyl, bis - [(C 1 -C 7 ) -alkyl] (aryl) silyl, bis-aryl [(C 1 -C 7 ) -alkyl] silyl, X 1 , X 2 and X 3 are identical or different and independently of one another are O (oxygen), S (sulfur), N (nitrogen), the group CR 2 or the group NR 20 , but in no case is an O and S atom are adjacent and wherein in each case more than one O or S atom in the formed 5-membered ring is not contained, and wherein R 2 in the group CR 2 and R 20 in the grouping NR 20 are the same or have different meanings according to the above or below definitions,
W für O (Sauerstoff) oder S (Schwefel) steht, W is O (oxygen) or S (sulfur),
A1, A2, A3, A4 und A5 gleich oder verschieden sind und unabhängig voneinander für N (Stickstoff) oder die Gruppierung C-R7 stehen, wobei jedoch in keinem Fall mehr als zwei N-Atome benachbart sind, und wobei R7 in der Gruppierung C-R7 jeweils gleiche oder verschiedene Bedeutungen gemäß der oben stehenden Definition hat, A 1 , A 2 , A 3 , A 4 and A 5 are the same or different and are independently N (nitrogen) or the group CR 7 , but in no case more than two N atoms are adjacent, and wherein R 7 in the group CR 7 has the same or different meanings as defined above,
R3 für (Ci-C7)-Alkyl, Cyano-(Ci-C7)-Alkyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (Ci-C7)-Haloalkyl, (C2-C7)-Haloalkenyl, (C2-C7)-Haloalkinyl, (C3-C7)- Cycloalkyl, (C3-C7)-Halocycloalkyl, (C -C7)-Cycloalkenyl, (C -C7)- Halocycloalkenyl, , Aryl, Aryl-(Ci-C7)-alkyl, Heteroaryl, Heteroaryl- (Ci-C7)-alkyl, (C3-C7)-Cycloalkyl-(Ci-C7)-alkyl, Heterocyclyl, Heterocyclyl- (Ci -C7)-al kyl , (Ci -C7)-Al koxy-(Ci -C7)-al kyl , (Ci-C7)-Al kylth io-(Ci -C7)-al kyl , (Ci-C7)-Haloalkoxy-(Ci-C7)-alkyl, (Ci-C7)-Haloalkylthio-(Ci-C7)-alkyl, R21R22N-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)-alkoxy-(Ci-C7)-alkyl steht, R 3 is (C 7) alkyl, cyano (Ci-C7) alkyl, (C 2 -C 7) alkenyl, (C 2 -C 7) alkynyl, (Ci-C7) - Haloalkyl, (C 2 -C 7 ) haloalkenyl, (C 2 -C 7 ) haloalkynyl, (C 3 -C 7 ) cycloalkyl, (C 3 -C 7 ) -halocycloalkyl, (C 7 -C 7 ) -cycloalkenyl , (C-C7) - Halocycloalkenyl, aryl, aryl (Ci-C7) alkyl, heteroaryl, heteroaryl (Ci-C7) alkyl, (C 3 -C 7) cycloalkyl (Ci- C 7 ) alkyl, heterocyclyl, heterocyclyl (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxy (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkyl keto - (Ci-C7) -alkyl, (Ci-C7) haloalkoxy (Ci-C7) alkyl, (Ci-C 7) -Haloalkylthio- (Ci-C7) alkyl, R 21 R 22 N- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl,
R4 für Wasserstoff, (Ci-C7)-Alkyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (Ci-C7)- Haloalkyl, (C2-C7)-Haloalkenyl, (C2-C7)-Haloalkinyl, (C3-C7)-Cycloalkyl, (C3-C7)-Halocycloalkyl, (C4-C7)-Cycloalkenyl, (C4-C7)-Halocycloalkenyl, Aryl, Aryl-(Ci-C7)-alkyl, Heteroaryl, Heteroaryl-(Ci-C7)-alkyl, (C3-C7)- Cycloalkyl-(Ci-C7)-alkyl, Heterocyclyl, Heterocyclyl-(Ci-C7)-alkyl, (Ci-C7)- Alkoxy-(Ci-C7)-alkyl, (Ci-C7)-Al kylth io-(Ci-C7)-al kyl, (Ci-C7)-Haloalkoxy- (Ci-C7)-alkyl, (Ci-C7)-Haloalkylthio-(Ci-C7)-alkyl, (Ci-C7)-Alkylamino- (Ci-C7)-alkyl, Bis-[(Ci-C7)-alkyl]amino-(Ci-C7)-alkyl, (C3-C7)- Cycloalkylamino-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)-alkoxy-(Ci-C7)- alkyl, COR23, (Ci-C7)-Alkoxycarbonyl, (C2-C7)-Alkenyloxycarbonyl, (C2-C7)-Alkinyloxycarbonyl, Aryl-(Ci-C7)-alkoxycarbonyl, Heteroaryl- (Ci -C7)-al koxycarbonyl , (C3-C7)-Cycloal kyl-(Ci -C7)-al koxycarbonyl , CONR21 R22, SO2R24, Hydroxycarbonyl-(Ci-C7)-alkyl, (Ci-C7)- Al koxycarbonyl-(Ci -C7)-al kyl , (C2-C7)-Al kenyloxycarbonyl-(Ci -C7)-al kyl , (C2-C7)-Al kinyloxycarbonyl-(Ci -C7)-al kyl , Aryl-(Ci -C7)-al koxycarbonyl- (Ci-C7)-alkyl, Heteroaryl-(Ci-C7)-alkoxycarbonyl-(Ci-C7)-alkyl, R 4 represents hydrogen, (Ci-C7) alkyl, (C 2 -C 7) alkenyl, (C 2 -C 7) alkynyl, (Ci-C7) - haloalkyl, (C 2 -C 7) Haloalkenyl, (C 2 -C 7 ) -haloalkynyl, (C 3 -C 7 ) -cycloalkyl, (C 3 -C 7 ) -halocycloalkyl, (C 4 -C 7 ) -cycloalkenyl, (C 4 -C 7 ) -Halocycloalkenyl, aryl, aryl (Ci-C7) alkyl, heteroaryl, heteroaryl (Ci-C7) alkyl, (C 3 -C 7) - cycloalkyl- (Ci-C7) alkyl, heterocyclyl, heterocyclyl- (Ci-C7) alkyl, (Ci-C7) - alkoxy (Ci-C7) alkyl, (Ci-C 7) -Al kylth io- (Ci-C7) -alkyl, (Ci-C7) haloalkoxy (Ci-C7) alkyl, (Ci-C 7) -Haloalkylthio- (Ci-C7) alkyl, (Ci-C7) alkylamino (Ci-C 7 ) alkyl, - bis [(Ci-C 7) alkyl] amino- (Ci-C7) alkyl, (C 3 -C 7) - Cycloalkylamino (Ci-C7) alkyl, (Ci-C7) alkoxy (Ci-C7) alkoxy (Ci-C7) - alkyl, COR 23, (Ci-C 7) alkoxycarbonyl, (C 2 -C 7) alkenyloxycarbonyl, (C2-C7) alkynyloxycarbonyl, aryl (Ci-C 7) alkoxycarbonyl, heteroaryl- (Ci -C 7) -al koxycarbonyl, (C3-C 7) -Cycloal alkyl- (Ci -C 7) -al koxycarbonyl, CONR 21 R 22, SO 2 R 24, hydroxycarbonyl (C 7) alkyl, (Ci-C7) - Al koxycarbonyl- (Ci-C7) - al kyl, (C2-C7) -Al kenyloxycarbonyl- (Ci-C7) -alkyl, (C2-C7) -Al kinyloxycarbonyl- (Ci-C7) -alkyl, aryl (Ci -C 7 ) -alkoxycarbonyl (C 1 -C 7 ) -alkyl, heteroaryl- (C 1 -C 7 ) -alkoxycarbonyl- (C 1 -C 7 ) -alkyl,
Heterocyclyl-(Ci-C7)-alkoxycarbonyl-(Ci-C7)-alkyl, (Ci-C7)-Alkylcarbonyl- (Ci-C7)-alkyl, (Ci-C7)-Alkylsulfonyl-(Ci-C7)-alkyl, (Ci-C7)-Alkylsulfinyl- (Ci-C7)-alkyl steht, Heterocyclyl- (C 1 -C 7 ) -alkoxycarbonyl- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkylcarbonyl- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkylsulfonyl- (C 1 -C 4 ) -alkylcarbonyl- C 7 ) -alkyl, (C 1 -C 7 ) -alkylsulfinyl- (C 1 -C 7 ) -alkyl,
R5 und R6 unabhängig voneinander für Wasserstoff, (Ci-C7)-Alkyl, (C2-C7)-R 5 and R 6 independently of one another represent hydrogen, (C 1 -C 7 ) -alkyl, (C 2 -C 7 ) -
Alkenyl, (C2-C7)-Alkinyl, (Ci-C7)-Haloalkyl, (C2-C7)-Haloalkenyl, (C2-C7)- Haloalkinyl, (C3-C7)-Cycloalkyl, (C3-C7)-Halocycloalkyl, (C -C7)- Cycloalkenyl, (C4-C7)-Halocycloalkenyl, Aryl, Aryl-(Ci-C7)-alkyl, Alkenyl, (C 2 -C 7) alkynyl, (Ci-C7) haloalkyl, (C 2 -C 7) haloalkenyl, (C 2 -C 7) - haloalkynyl, (C 3 -C 7) cycloalkyl , (C 3 -C 7 ) -halocycloalkyl, (C 7 -C 7 ) -cycloalkenyl, (C 4 -C 7 ) -halocycloalkenyl, aryl, aryl- (C 1 -C 7 ) -alkyl,
Heteroaryl, Heteroaryl-(Ci-C7)-alkyl, (C3-C7)-Cycloalkyl-(Ci-C7)-alkyl, Heterocyclyl , Heterocyclyl-(Ci -C7)-al kyl , (C1 -C7)-Al koxy-(Ci -C7)-al kyl , (C 1 -C7)-Al ky Ith io-(C 1 -C7)-al ky I , (Ci-C7)-Haloalkoxy-(Ci-C7)-alkyl, (Ci-C7)- Haloalkylthio-(Ci-C7)-alkyl, COOR23, CONR21 R22, Hydroxycarbonyl- (Ci-C7)-alkyl, (Ci-C7)-Alkoxycarbonyl-(Ci-C7)-alkyl, (C2-C7)- Al kenyloxycarbonyl-(Ci -C7)-al kyl , (C2-C7)-Al kinyloxycarbonyl-(Ci -C7)- alkyl, Aryl-(Ci-C7)-alkoxycarbonyl-(Ci-C7)-alkyl, Heteroaryl-(Ci-C7)- alkoxycarbonyl-(Ci-C7)-alkyl, Heterocyclyl-(Ci-C7)-alkoxycarbonyl- (Ci-C7)-alkyl stehen, Heteroaryl, heteroaryl (Ci-C7) alkyl, (C 3 -C 7) cycloalkyl (Ci-C7) alkyl, heterocyclyl, heterocyclyl (Ci-C7) -alkyl, (C 1 -C 7 ) -Al koxy- (Ci -C 7 ) -alcyl, (C 1 -C 7 ) -Al ky Ith io- (C 1 -C 7 ) -alkenyl, (Ci-C 7 ) -haloalkoxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkylthio (C 1 -C 7 ) -alkyl, COOR 23 , CONR 21 R 22 , hydroxycarbonyl- (C 1 -C 7 ) -alkyl, (Ci-C 7 ) alkoxycarbonyl- (Ci-C 7 ) alkyl, (C 2 -C 7 ) - Al kenyloxycarbonyl- (Ci -C 7 ) -al kyl, (C 2 -C 7 ) -Al kinyloxycarbonyl- (Ci -C 7 ) - alkyl, aryl- (Ci-C 7 ) -alkoxycarbonyl- (Ci-C 7 ) -alkyl, heteroaryl- (Ci-C 7 ) - alkoxycarbonyl- (Ci-C 7 ) -alkyl, heterocyclyl- (Ci-C 7 ) -alkoxycarbonyl- (C 1 -C 7 ) -alkyl,
R3 und R4 mit dem Stickstoffatom, an das sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfall durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3-7-gliedrigen Ring bilden, R 3 and R 4 with the nitrogen atom to which they are attached form a completely saturated, partially saturated or completely unsaturated, optionally interrupted by heteroatoms and optionally further substituted 3-7-membered ring,
R1 und X1 , wenn X1 für eine Gruppe C-R2 steht, mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden, R 1 and X 1 , when X 1 is a group CR 2 , with the atoms to which they are attached, a fully saturated, partially saturated or fully unsaturated, optionally by heteroatoms form interrupted and optionally further substituted 5-7 membered ring,
X1 und X2, wenn beide für eine Gruppe C-R2 stehen, mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfalls durch Heteroatome X 1 and X 2 , when both represent a group CR 2 , with the atoms to which they are attached, a fully saturated, partially saturated or fully unsaturated, optionally by heteroatoms
unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden, A1 und A2, wenn beide für eine Gruppe C-R7 stehen, mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfalls durch Heteroatome form interrupted and optionally further substituted 5-7 membered ring, A 1 and A 2 , when both represent a group CR 7 , with the atoms to which they are attached, a fully saturated, partially saturated or fully unsaturated, optionally by heteroatoms
unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden,  form interrupted and optionally further substituted 5-7 membered ring,
A2 und A3, wenn beide für eine Gruppe C-R7 stehen, mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfalls durch Heteroatome A 2 and A 3 , when both represent a group CR 7 , with the atoms to which they are attached, a fully saturated, partially saturated or fully unsaturated, optionally by heteroatoms
unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden und  form interrupted and optionally further substituted 5-7 membered ring and
A3 und A4, wenn beide für eine Gruppe C-R7 stehen, mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfalls durch Heteroatome A 3 and A 4 , when both represent a group CR 7 , with the atoms to which they are attached, a fully saturated, partially saturated or fully unsaturated, optionally by heteroatoms
unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen interrupted and optionally further substituted 5-7 membered
Ring bilden, Form ring,
Y für eine Bindung oder für die Gruppierungen Y-1 bis Y-7 Y for a bond or for the groupings Y-1 to Y-7
Υ-5 steht, wobei R8, R9, R10, R1 1 , R12, R13, R14, R15, R16, R17, R18 und R19 jeweils die Bedeutung gemäß der nachstehenden Definition haben und wobei der Pfeil für eine Bindung zum 6-gliedrigen Ring mit den Υ-5 , wherein R 8, R 9, R 10, R 1 1, R 12, R 13, R 14, R 15, R 16, R 17, R 18 and R 19 each have the meaning as defined below, and wherein the Arrow for a bond to the 6-membered ring with the
Gruppierungen A1 , A2, A3, A4 und A5 steht, Groups A 1 , A 2 , A 3 , A 4 and A 5 ,
R8, R9, R10, R1 1 , R12, R13, R14, R15, R16, R17, R18 und R19 unabhängig R 8, R 9, R 10, R 1 1, R 12, R 13, R 14, R 15, R 16, R 17, R 18 and R 19 are independently
voneinander für Wasserstoff, Halogen, (Ci-C7)-Alkyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (Ci-C7)-Haloalkyl, (C2-C7)-Haloalkenyl, (C2-C7)- Haloalkinyl, (C3-C7)-Cycloalkyl, Aryl, Aryl-(Ci-C7)-alkyl, Heteroaryl, Heteroaryl-(Ci-C7)-alkyl, (C3-C7)-Cycloalkyl-(Ci-C7)-alkyl, Heterocyclyl, Heterocyclyl-(Ci -C7)-al kyl , (C1 -C7)-Al koxy-(Ci -C7)-al kyl , (C1 -C7)-Al kylth io- (Ci-C7)-alkyl, (Ci-C7)-Haloalkoxy-(Ci-C7)-alkyl, (Ci-C7)-Haloalkylthio- (Ci-C7)-alkyl, COOR23 stehen, represent hydrogen, halogen, (Ci-C7) alkyl, (C2-C7) alkenyl, (C 2 -C 7) alkynyl, (Ci-C7) haloalkyl, (C 2 -C 7) haloalkenyl , (C2-C7) - haloalkynyl, (C 3 -C 7) cycloalkyl, aryl, aryl (Ci-C7) alkyl, heteroaryl, heteroaryl (Ci-C7) alkyl, (C3-C 7 ) -Cycloalkyl- (C 1 -C 7 ) -alkyl, heterocyclyl, heterocyclyl- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, (Cl - C 7 ) -Al kylth io- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkoxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkylthio (C 1 -C 7 ) alkyl, COOR 23 ,
R5 und R6 mit dem Atom, an das sie gebunden sind, einen vollständig R 5 and R 6 with the atom to which they are attached, a complete
gesättigten, oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden,  form saturated, or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring,
R20 für Wasserstoff, (Ci-C7)-Alkyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (C1-C7)- Haloalkyl, (C2-C7)-Haloalkenyl, (C2-C7)-Haloalkinyl, (C3-C7)-Cycloalkyl, (C4-C7)-Cycloalkenyl, (Ci-C7)-Alkoxy, Aryl, Heteroaryl, Heterocyclyl, (Ci-C7)-Alkylcarbonyl, Aryl-(Ci-C7)-Alkylcarbonyl, (C3-C7)- Cycloalkylcarbonyl, Arylcarbonyl, Heteroarylcarbonyl, (C1-C7)- Alkoxycarbonyl, (C2-C7)-Alkenyloxycarbonyl, Aryl-(Ci-C7)-alkoxycarbonyl, Heteroaryl-(Ci-C7)-alkoxycarbonyl, (C3-C7)-Cycloalkyl-(Ci-C7)- alkoxycarbonyl, (Ci-C7)-Alkylsulfonyl, (Ci-C7)-Haloalkylsulfonyl, R 20 represents hydrogen, (C 1 -C 7 ) -alkyl, (C 2 -C 7 ) -alkenyl, (C 2 -C 7 ) -alkynyl, (C 1 -C 7 ) -haloalkyl, (C 2 -C 7 ) - Haloalkenyl, (C 2 -C 7 ) -haloalkynyl, (C 3 -C 7 ) -cycloalkyl, (C 4 -C 7 ) -cycloalkenyl, (C 1 -C 7 ) -alkoxy, aryl, heteroaryl, heterocyclyl, (C 1 -C 7 ) -Alkylcarbonyl, aryl- (C 1 -C 7 ) -alkylcarbonyl, (C 3 -C 7 ) -cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, (C 1 -C 7) -alkoxycarbonyl, (C 2 -C 7) -alkenyloxycarbonyl, aryl- (C 1 -C 7 ) -alkoxycarbonyl Heteroaryl (C 1 -C 7) -alkoxycarbonyl, (C 3 -C 7) -cycloalkyl- (C 1 -C 7) -alkoxycarbonyl, (C 1 -C 7) -alkylsulfonyl, (C 1 -C 7) -haloalkylsulfonyl,
Arylsulfonyl, Heteroarylsulfonyl, (C3-C7)-Cycloalkylsulfonyl, (C1-C7)- Alkylsulfinyl, Arylsulfinyl, Heteroarylsulfinyl, (C3-C7)-Cycloalkylsulfinyl steht, n für 0, 1 oder 2 steht  Arylsulfonyl, heteroarylsulfonyl, (C 3 -C 7) -cycloalkylsulfonyl, (C 1 -C 7) -alkylsulfinyl, arylsulfinyl, heteroarylsulfinyl, (C 3 -C 7) -cycloalkylsulfinyl, n is 0, 1 or 2
R21 und R22 gleich oder verschieden sind und unabhängig voneinander für Wasserstoff, (Ci-C7)-Alkyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (C1-C7)- Cyanoalkyl, (Ci-C7)-Haloalkyl, (C2-C7)-Haloalkenyl, (C2-C7)-Haloalkinyl, (C3-C7)-Cycloalkyl, (C3-C7)-Halocycloalkyl, (C -C7)-Cycloalkenyl, (C -C7)- Halocycloalkenyl, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, (Ci-C7)-Haloalkoxy- (Ci-C7)-alkyl, (C1 -C7)-Al kylth io-(Ci -C7)-al kyl , (Ci-C7)-Haloalkylthio- (Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)-haloalkyl, Aryl, Aryl-(Ci-C7)-alkyl, Heteroaryl, Heteroaryl-(Ci-C7)-alkyl, (C3-C7)-Cycloalkyl-(Ci-C7)-alkyl, (C4-C7)-Cycloalkenyl-(Ci-C7)-alkyl, COR23, SO2R24, -(Ci-C7)-Alkyl- HNO2S-, (C3-C7)-Cycloalkyl-HNO2S-, Heterocyclyl, (C1-C7)- Alkoxycarbonyl-(Ci-C7)-alkyl, (Ci-C7)-Alkoxycarbonyl, Aryl-(Ci-C7)- Alkoxycarbonyl-(Ci-C7)-alkyl, Aryl-(Ci-C7)-Alkoxycarbonyl, Heteroaryl- (Ci-C7)-Alkoxycarbonyl, (C2-C7)-Alkenyloxycarbonyl, (C2-C7)- Alkinyloxycarbonyl, Heterocyclyl-(Ci-C7)-alkyl stehen R 21 and R 22 are identical or different and are each independently hydrogen, (Ci-C7) alkyl, (C 2 -C 7) alkenyl, (C 2 -C 7) alkynyl, (C1-C7) - Cyanoalkyl, (C 1 -C 7 ) -haloalkyl, (C 2 -C 7 ) -haloalkenyl, (C 2 -C 7 ) -haloalkynyl, (C 3 -C 7 ) -cycloalkyl, (C 3 -C 7 ) -halocycloalkyl , (C-C7) cycloalkenyl, (C -C 7) - (Halocycloalkenyl, (Ci-C7) alkoxy (Ci-C7) alkyl, (Ci-C7) haloalkoxy Ci-C 7) alkyl, (C1-C7) -alkyl kylth io- (Ci-C7) -alkyl, (Ci-C 7) -Haloalkylthio- (Ci-C7) alkyl, (Ci-C 7) Alkoxy- (C 1 -C 7 ) -haloalkyl, aryl, aryl- (C 1 -C 7 ) -alkyl, heteroaryl, heteroaryl- (C 1 -C 7 ) -alkyl, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 4 ) -alkyl, C 7) alkyl, (C 4 -C 7) cycloalkenyl (C 7) alkyl, COR 23, SO 2 R 24, - (Ci-C7) alkyl- HNO 2 S-, (C 3 -C 7) -cycloalkyl-HNO 2 S, heterocyclyl, (C1-C7) - alkoxycarbonyl (Ci-C7) alkyl, (Ci-C 7) alkoxycarbonyl, aryl (Ci-C7) - alkoxycarbonyl (Ci-C7) alkyl, aryl (Ci-C7) alkoxycarbonyl, heteroaryl- (Ci-C7) -alkoxycarbonyl, (C2-C7) alkenyloxycarbonyl, (C 2 -C 7) - Alkynyloxycarbonyl, heterocyclyl (Ci-C7) alkyl
R23 für Wasserstoff, (Ci-C7)-Alkyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (C1-C7)- Cyanoalkyl, (Ci-C7)-Haloalkyl, (C2-C7)-Haloalkenyl, (C2-C7)-Haloalkinyl, (C3-C7)-Cycloalkyl, (C3-C7)-Halocycloalkyl, (C -C7)-Cycloalkenyl, (C -C7)- Halocycloalkenyl, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)- haloalkyl, Aryl, Aryl-(Ci-C7)-alkyl, Heteroaryl, Heteroaryl-(Ci-C7)-alkyl, (C3-C7)-Cycloalkyl-(Ci-C7)-alkyl, (C -C7)-Cycloalkenyl-(Ci-C7)-alkyl, (C1 -C7)-Al koxycarbonyl-(Ci -C7)-al kyl , (C2-C7)-Al kenyloxycarbonyl-(Ci -C7) alkyl, Aryl-(Ci-C7)-Alkoxycarbonyl-(Ci-C7)-alkyl, Hydroxycarbonyl-(Ci-C7) alkyl, Heterocyclyl, Heterocyclyl-(Ci-C7)-alkyl steht und für Wasserstoff, (Ci-C7)-Alkyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (Ci-C7)- Cyanoalkyl, (Ci-C7)-Haloalkyl, (C2-C7)-Haloalkenyl, (C2-C7)-Haloalkinyl, (C3-C7)-Cycloalkyl, (C3-C7)-Halocycloalkyl, (C -C7)-Cycloalkenyl, (C -C7)- Halocycloalkenyl, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)- haloalkyl, Aryl, Aryl-(Ci-C7)-alkyl, Heteroaryl, Heteroaryl-(Ci-C7)-alkyl, Heterocyclyl-(Ci -C7)-alkyl , (C3-C7)-Cycloal kyl-(Ci -C7)-al kyl , (C -C7)- Cycloalkenyl-(Ci-C7)-alkyl, NR21R22 steht. R 23 is hydrogen, (Ci-C7) alkyl, (C 2 -C 7) alkenyl, (C 2 -C 7) alkynyl, (C1-C7) - cyanoalkyl, (Ci-C 7) -haloalkyl , (C 2 -C 7 ) -haloalkenyl, (C 2 -C 7 ) -haloalkynyl, (C 3 -C 7 ) -cycloalkyl, (C 3 -C 7 ) -halocycloalkyl, (C 7 -C 7 ) -cycloalkenyl, (C-C7) - Halocycloalkenyl, (Ci-C7) alkoxy (Ci-C7) alkyl, (Ci-C7) alkoxy (Ci-C7) - haloalkyl, aryl, aryl ( Ci-C 7) alkyl, heteroaryl, heteroaryl (Ci-C7) alkyl, (C3-C7) -cycloalkyl- (Ci-C7) alkyl, (C-C7) cycloalkenyl (C -C 7) alkyl, (C1-C7) -alkyl koxycarbonyl- (Ci-C7) -alkyl, (C 2 -C 7) -alkyl kenyloxycarbonyl- (Ci-C7) alkyl, aryl (C -C 7) alkoxycarbonyl- (C 1 -C 7) -alkyl, hydroxycarbonyl- (C 1 -C 7) -alkyl, heterocyclyl, heterocyclyl- (C 1 -C 7) -alkyl and is hydrogen, (Ci-C7) alkyl, (C 2 -C 7) alkenyl, (C 2 -C 7) alkynyl, (Ci-C7) - cyanoalkyl, (Ci-C7) haloalkyl, (C 2 -C 7 ) -haloalkenyl, (C 2 -C 7 ) -haloalkynyl, (C 3 -C 7 ) -cycloalkyl, (C 3 -C 7 ) -halocycloalkyl, (C 2 -C 7 ) -cycloalkenyl, ( C -C 7) - Halocycloalkenyl, (Ci-C7) alkoxy (Ci-C7) alkyl, (Ci-C7) alkoxy (Ci-C7) - haloalkyl, aryl, aryl (C -C 7 ) alkyl, heteroaryl, heteroaryl (Ci-C 7 ) alkyl, heterocyclyl (Ci -C 7 ) alkyl, (C 3 -C 7 ) -Cycloal kyl- (Ci -C 7 ) -al alkyl, (C-C7) - cycloalkenyl (Ci-C7) alkyl, NR 21 R 22.
Substituierte Heteroarylcarbonsäurehydrazide gemäß Anspruch 1 , wobei Substituted heteroarylcarboxylic acid hydrazides according to claim 1, wherein
R1, R2 und R7 unabhängig voneinander für Wasserstoff, Halogen, Cyano, Nitro, NR21R22, OR23, S(O)nR24, Thiocyanato, Isothiocyanato, (Ci-C6)-Alkyl, (C2-C6)-Al kenyl, (C2-C6)-Alkinyl, (Ci-C6)-Haloalkyl, (C2-C6)-Haloalkenyl, (C2-C6)-Haloalkinyl, (C3-C6)-Cycloalkyl, (C3-C6)-Halocycloalkyl, (C -C6)- Cycloalkenyl, (C4-C6)-Halocycloalkenyl, Pentafluorthio, (Ci-Ce)-Alkoxy- (Ci-C6)-haloalkyl, (Ci-C6)-Haloalkoxy-(Ci-C6)-haloalkyl, (Ci-C6)- Haloalkoxy-(Ci-C6)-alkyl, Aryl, Aryl-(Ci-C6)-alkyl, Heteroaryl, Heteroaryl- (Ci -C6)-al kyl , (C3-C6)-Cycloal kyl-(Ci -C6)-al kyl , (C -C6)-Cycloal kenyl- (Ci-C6)-alkyl, Heterocyclyl, Heterocyclyl-(Ci-C6)-alkyl, (Ci-Ce)-Alkoxy- (Ci-C6)-alkyl, (Ci -C6)-Al kylth io-(Ci -C6)-al kyl , (Ci-C6)-Haloalkylthio- (Ci-C6)-alkyl, (Ci-C6)-Alkylcarbonyl-(Ci-C6)-alkyl, COOR23, CONR21R22, COR23 , -C=NOR23, R21R22N-(Ci-C6)-alkyl, R23OOC-(Ci-C6)-alkyl, Aryl- (Ci-C6)-alkinyl, Heteroaryl-(Ci-C6)-alkinyl, Heterocyclyl-(Ci-C6)-alkinyl, Tris-[(Ci-C6)-alkyl]silyl-(C2-C6)-alkinyl, Bis-[(Ci-C6)-alkyl](aryl)silyl-(C2-C6)- alkinyl, Bis-aryl[(Ci-C6)-alkyl]silyl-(C2-C6)-alkinyl, (C3-C6)-Cycloalkyl- (C2-C6)-al kinyl , Aryl-(C2-C6)-al kenyl , Heteroaryl-(C2-C6)-al kenyl , R 1 , R 2 and R 7 independently of one another represent hydrogen, halogen, cyano, nitro, NR 21 R 22 , OR 23 , S (O) n R 24 , thiocyanato, isothiocyanato, (C 1 -C 6 ) -alkyl, (C 2 -C 6) -alkenyl, (C 2 -C 6) alkynyl, (Ci-C 6) -haloalkyl, (C 2 -C 6) haloalkenyl, (C 2 -C 6) haloalkynyl, (C3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -halocycloalkyl, (C -C 6 ) -cycloalkenyl, (C 4 -C 6 ) -halocycloalkenyl, pentafluorothio, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) haloalkyl, (C 1 -C 6 ) -haloalkoxy- (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -haloalkoxy- (C 1 -C 6 ) -alkyl, aryl, aryl- (C 1 -C 6 ) -alkyl, heteroaryl , heteroaryl (Ci-C6) -alkyl, (C 3 -C 6) -Cycloal alkyl- (Ci-C6) -alkyl, (C-C6) -Cycloal kenyl- (Ci-C 6) alkyl, heterocyclyl, heterocyclyl (Ci-C 6) alkyl, (Ci-Ce) alkoxy (Ci-C 6) alkyl, (Ci-C6) -alkyl kylth io- (Ci-C6) -alkyl, (C 1 -C 6 ) -haloalkylthio (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylcarbonyl- (C 1 -C 6 ) -alkyl, COOR 23 , CONR 21 R 22 , COR 23 , -C = NOR 23 , R 21 R 22 N- (C 1 -C 6 ) -alkyl, R 23 OOC- (C 1 -C 6 ) -alkyl, aryl- (C 1 -C 6 ) -alkynyl, heteroar yl- (Ci-C6) alkynyl, heterocyclyl (Ci-C6) alkynyl, tris - [(Ci-C6) alkyl] silyl (C 2 -C 6 ) alkynyl, bis - [(Ci-C6 ) -alkyl] (aryl) silyl- (C 2 -C 6 ) -alkynyl, bis-aryl [(C 1 -C 6 ) -alkyl] silyl- (C 2 -C 6 ) -alkynyl, (C 3 -C 6 ) - Cycloalkyl- (C 2 -C 6 ) -alkenyl, aryl- (C 2 -C 6 ) -alkenyl, heteroaryl- (C 2 -C 6 ) -alkenyl,
Heterocyclyl-(C2-C6)-al kenyl , (C3-C6)-Cycloal kyl-(C2-C6)-al kenyl , (Ci -C6)- Alkoxy-(Ci-C6)-alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkylaminosulfonylamino, (C3-C6)-Cycloalkylaminosulfonylamino, Diazo, Aryldiazo stehen, Heterocyclyl (C 2 -C 6) -alkenyl, (C 3 -C 6) -Cycloal alkyl- (C 2 -C 6) -alkenyl, (Ci-C6) - alkoxy- (Ci-C6) - alkoxy- (C 1 -C 6) -alkyl, (C 1 -C 6) -alkylaminosulfonylamino, (C 3 -C 6) -cycloalkylaminosulfonylamino, diazo, aryldiazo,
X1, X2 und X3 gleich oder verschieden sind und unabhängig voneinander für O (Sauerstoff), S (Schwefel), N (Stickstoff), die Gruppierung C-R2 oder die Gruppierung N-R20 stehen, wobei jedoch in keinem Fall ein O- und S- Atom benachbart sind und wobei in keinem Fall jeweils mehr als ein O- oder S-Atom im gebildeten 5-gliedrigen Ring enthalten ist, und wobei R2 in der Gruppierung C-R2 und R20 in der Gruppierung N-R20 jeweils gleiche oder verschiedene Bedeutungen gemäß der oben- oder nachstehenden Definitionen haben, X 1 , X 2 and X 3 are identical or different and independently of one another are O (oxygen), S (sulfur), N (nitrogen), the group CR 2 or the group NR 20 , but in no case is an O and S- Atom are adjacent and wherein in each case more than one O or S atom in the formed 5-membered ring is contained, and wherein R 2 in the group CR 2 and R 20 in the grouping NR 20 each have the same or different meanings according to have the above or below definitions,
W für O (Sauerstoff) oder S (Schwefel) steht, W is O (oxygen) or S (sulfur),
A1 , A2, A3, A4 und A5 gleich oder verschieden sind und unabhängig voneinander für N (Stickstoff) oder die Gruppierung C-R7 stehen, wobei jedoch in keinem Fall mehr als zwei N-Atome benachbart sind, und wobei R7 in der Gruppierung C-R7 jeweils gleiche oder verschiedene Bedeutungen gemäß der oben stehenden Definition hat, A 1 , A 2 , A 3 , A 4 and A 5 are the same or different and are independently N (nitrogen) or the group CR 7 , but in no case more than two N atoms are adjacent, and wherein R 7 in the group CR 7 has the same or different meanings as defined above,
R3 für (Ci-C6)-Alkyl, Cyano-(Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (Ci-C6)-Haloalkyl, (C2-C6)-Haloalkenyl, (C2-C6)-Haloalkinyl, (C3-C6)- Cycloalkyl, (C3-C6)-Halocycloalkyl, (C -C6)-Cycloalkenyl, (C -C6)- Halocycloalkenyl, , Aryl, Aryl-(Ci-C6)-alkyl, Heteroaryl, Heteroaryl- (Ci-C6)-alkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, Heterocyclyl, Heterocyclyl- (Ci -C6)-al kyl , (Ci -C6)-Al koxy-(Ci -C6)-alkyl , (Ci-C6)-Al kylth io-(Ci -C6)-al kyl , (Ci-C6)-Haloalkoxy-(Ci-C6)-alkyl, (Ci-C6)-Haloalkylthio-(Ci-C6)-alkyl, R21 R22N-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxy-(Ci-C6)-alkyl steht, R 3 is (C 1 -C 6 ) -alkyl, cyano- (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (C 1 -C 6 ) -haloalkyl, (C2-C6) haloalkenyl, (C2-C6) haloalkynyl, (C 3 -C 6) - cycloalkyl, (C3-C 6) halocycloalkyl, (C-C6) cycloalkenyl, (C -C 6 ) - halocycloalkenyl,, aryl, aryl- (C 1 -C 6 ) -alkyl, heteroaryl, heteroaryl- (C 1 -C 6) -alkyl, (C 3 -C 6) -cycloalkyl- (C 1 -C 6) -alkyl, heterocyclyl, heterocyclyl- (C 1 -C 6 ) -alkenyl, (C 1 -C 6 ) -alkoxy (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkylthio (C 1 -C 6 ) -alkyl, R 21 R 22 N- (C 1 -C 6 ) -alkyl, ( C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl,
R4 für Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (Ci-C6)- Haloalkyl, (C2-C6)-Haloalkenyl, (C2-C6)-Haloalkinyl, (C3-C6)-Cycloalkyl, (C3-C6)-Halocycloalkyl, (C4-C6)-Cycloalkenyl, (C4-C6)-Halocycloalkenyl, Aryl, Aryl-(Ci-C6)-alkyl, Heteroaryl, Heteroaryl-(Ci-C6)-alkyl, (C3-C6)- Cycloalkyl-(Ci-C6)-alkyl, Heterocyclyl, Heterocyclyl-(Ci-C6)-alkyl, (C1-C6)- Alkoxy-(Ci-C6)-alkyl, (Ci-Ce)-Al kylth io-(Ci-C6)-al kyl, (Ci-Ce)-Haloalkoxy- (Ci-C6)-alkyl, (Ci-C6)-Haloalkylthio-(Ci-C6)-alkyl, (Ci-C6)-Alkylamino- (Ci-C6)-alkyl, Bis-[(Ci-C6)-alkyl]amino-(Ci-C6)-alkyl, (C3-C6)- Cycloalkylamino-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxy-(Ci-C6)- alkyl, COR23, (Ci-C6)-Alkoxycarbonyl, (C2-C6)-Alkenyloxycarbonyl, (C2-C6)-Alkinyloxycarbonyl, Aryl-(Ci-C6)-alkoxycarbonyl, Heteroaryl- (Ci -C6)-al koxycarbonyl , (C3-C6)-Cycloal kyl-(Ci -C6)-al koxycarbonyl , CONR21R22, SO2R24, Hydroxycarbonyl-(Ci-C6)-alkyl, (Ci-C6)- Al koxycarbonyl-(Ci -C6)-al kyl , (C2-C6)-Al kenyloxycarbonyl-(Ci -C6)-al kyl , (C2-C6)-Al kinyloxycarbonyl-(Ci -C6)-al kyl , Aryl-(Ci -C6)-al koxycarbonyl- (Ci-C6)-alkyl, Heteroaryl-(Ci-C6)-alkoxycarbonyl-(Ci-C6)-alkyl, R 4 represents hydrogen, (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) -alkynyl, (Ci-C 6) - haloalkyl, (C2-C6) - haloalkenyl, (C2-C6) haloalkynyl, (C3-C6) -cycloalkyl, (C3-C6) halocycloalkyl, (C 4 -C 6) cycloalkenyl, (C 4 -C 6) -Halocycloalkenyl, aryl, aryl (C 1 -C 6 ) -alkyl, heteroaryl, heteroaryl- (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, heterocyclyl, heterocyclyl- (C 1 -C 6 ) - alkyl, (C 1 -C 6 ) -alkoxy (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkoxy- (C 1 -C 4 ) -alkyl C 6 ) -alkyl, (C 1 -C 6 ) -haloalkylthio (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylamino (C 1 -C 6 ) -alkyl, bis - [(C 1 -C 6 ) - alkyl] amino- (Ci-C 6) alkyl, (C 3 -C 6) - cycloalkylamino (Ci-C 6) alkyl, (Ci-C6) alkoxy (Ci-C6) alkoxy (Ci -C 6 ) -alkyl, COR 23 , (C 1 -C 6 ) -alkoxycarbonyl, (C 2 -C 6 ) -alkenyloxycarbonyl, (C 2 -C 6 ) -alkynyloxycarbonyl, aryl- (C 1 -C 6 ) -alkoxycarbonyl, heteroaryl (C 1 -C 6 ) -alkoxycarbonyl, (C 3 -C 6 ) -cycloalkyl (C 1 -C 6 ) -alkoxycarbonyl, CONR 21 R 22 , SO 2 R 24 , hydroxycarbonyl- (C 1 -C 6 ) -alkyl, (Ci -C 6 ) - alkoxycarbonyl- (C 1 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkhenyloxycarbonyl- (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkynyloxycarbonyl- (C 1 -C 6 ) - al kyl, aryl- (C 1 -C 6) -alkoxycarbonyl- (C 1 -C 6) -alkyl, heteroaryl- (C 1 -C 6) -alkoxycarbonyl- (C 1 -C 6) -alkyl,
Heterocyclyl-(Ci-C6)-alkoxycarbonyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylcarbonyl- (Ci-C6)-alkyl, (Ci-C6)-Alkylsulfonyl-(Ci-C6)-alkyl, (Ci-C6)-Al kylsulfinyl- (Ci-Ce)-alkyl steht, Heterocyclyl- (C 1 -C 6 ) -alkoxycarbonyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylcarbonyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylsulfonyl- (C 1 -C 6 ) - alkyl, (C 1 -C 6 ) -alkylsulfinyl- (C 1 -C 6 ) -alkyl,
R5 und R6 unabhängig voneinander für Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-R 5 and R 6 independently of one another represent hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6) -
Alkenyl, (C2-C6)-Alkinyl, (Ci-C6)-Haloalkyl, (C2-C6)-Haloalkenyl, (C2-C6)- Haloalkinyl, (C3-C6)-Cycloalkyl, (C3-C6)-Halocycloalkyl, (C -C6)- Cycloalkenyl, (C4-C6)-Halocycloalkenyl, Aryl, Aryl-(Ci-C6)-alkyl, Alkenyl, (C2-C6) -alkynyl, (Ci-C 6) -haloalkyl, (C2-C6) haloalkenyl, (C 2 -C 6) - haloalkynyl, (C3-C6) -cycloalkyl, (C3 -C 6 ) -halocycloalkyl, (C -C 6 ) -cycloalkenyl, (C 4 -C 6 ) -halocycloalkenyl, aryl, aryl- (C 1 -C 6 ) -alkyl,
Heteroaryl, Heteroaryl-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, Heterocyclyl , Heterocyclyl-(Ci -C6)-al kyl , (C1 -C6)-Al koxy-(Ci -C6)-al kyl , (Ci-C6)-Alkylthio-(Ci-C6)-alkyl, (Ci-C6)-Haloalkoxy-(Ci-C6)-alkyl, (Ci-C6)- Haloalkylthio-(Ci-C6)-alkyl, COOR23, CONR21 R22, Hydroxycarbonyl- (Ci-C6)-alkyl, (Ci-C6)-Alkoxycarbonyl-(Ci-C6)-alkyl, (C2-C6)- Al kenyloxycarbonyl-(Ci -C6)-al kyl , (C2-C6)-Al kinyloxycarbonyl-(Ci -Ce)- alkyl, Aryl-(Ci-C6)-alkoxycarbonyl-(Ci-C6)-alkyl, Heteroaryl-(Ci-C6)- alkoxycarbonyl-(Ci-C6)-alkyl, Heterocyclyl-(Ci-C6)-alkoxycarbonyl- (Ci-C6)-alkyl stehen, Heteroaryl, heteroaryl (Ci-C 6) alkyl, (C3-C6) cycloalkyl (Ci-C 6) alkyl, heterocyclyl, heterocyclyl (Ci-C6) -alkyl, (C1-C6) -Al alkoxy- (Ci-C6) -alkyl, (Ci-C6) alkylthio (Ci-C 6) alkyl, (Ci-C6) haloalkoxy (Ci-C 6) alkyl, (C -C 6 ) - haloalkylthio (C 1 -C 6 ) -alkyl, COOR 23 , CONR 21 R 22 , hydroxycarbonyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxycarbonyl- (C 1 -C 6 ) - alkyl, (C 2 -C 6 ) -alkenyloxycarbonyl- (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkynyloxycarbonyl- (C 1 -C 6 ) -alkyl, aryl- (C 1 -C 6 ) -alkoxycarbonyl- C 1 -C 6) -alkyl, heteroaryl- (C 1 -C 6) -alkoxycarbonyl- (C 1 -C 6) -alkyl, heterocyclyl- (C 1 -C 6) -alkoxycarbonyl- (C 1 -C 6) -alkyl,
R3 und R4 mit dem Stickstoffatom, an das sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfall durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3-7-gliedrigen Ring bilden, R 3 and R 4 with the nitrogen atom to which they are attached form a completely saturated, partially saturated or completely unsaturated, optionally interrupted by heteroatoms and optionally further substituted 3-7-membered ring,
R1 und X1, wenn X1 für eine Gruppe C-R2 steht, mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfalls durch Heteroatome R 1 and X 1 , when X 1 is a group CR 2 , with the atoms to which they are attached, a fully saturated, partially saturated or fully unsaturated, optionally by heteroatoms
unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden, X1 und X2, wenn beide für eine Gruppe C-R2 stehen, mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfalls durch Heteroatome form interrupted and optionally further substituted 5-7 membered ring, X 1 and X 2 , when both represent a group CR 2 , with the atoms to which they are attached, a fully saturated, partially saturated or fully unsaturated, optionally by heteroatoms
unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden,  form interrupted and optionally further substituted 5-7 membered ring,
A1 und A2, wenn beide für eine Gruppe C-R7 stehen, mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfalls durch Heteroatome A 1 and A 2 , when both represent a group CR 7 , with the atoms to which they are attached, a fully saturated, partially saturated or fully unsaturated, optionally by heteroatoms
unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen interrupted and optionally further substituted 5-7 membered
Ring bilden, Form ring,
A2 und A3, wenn beide für eine Gruppe C-R7 stehen, mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfalls durch Heteroatome A 2 and A 3 , when both represent a group CR 7 , with the atoms to which they are attached, a fully saturated, partially saturated or fully unsaturated, optionally by heteroatoms
unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden und  form interrupted and optionally further substituted 5-7 membered ring and
A3 und A4, wenn beide für eine Gruppe C-R7 stehen, mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder vollständig ungesättigten, gegebenenfalls durch Heteroatome A 3 and A 4 , when both represent a group CR 7 , with the atoms to which they are attached, a fully saturated, partially saturated or fully unsaturated, optionally by heteroatoms
unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden, Y für eine Bindung oder für die Gruppierungen Y-1 bis Y-7  form interrupted and optionally further substituted 5-7 membered ring, Y for a bond or for the groupings Y-1 to Y-7
Y-1 Y-2 Y-3 Y-4 Y-5 Y-1 Y-2 Y-3 Y-4 Y-5
steht, wobei R8, R9, R10, R1 1, R12, R13, R14, R15, R16, R17, R18 und R19 jeweils die Bedeutung gemäß der nachstehenden Definition haben und wobei der Pfeil für eine Bindung zum 6-gliedrigen Ring mit den , wherein R 8, R 9, R 10, R 1 1, R 12, R 13, R 14, R 15, R 16, R 17, R 18 and R 19 each have the meaning as defined below, and wherein the Arrow for a bond to the 6-membered ring with the
Gruppierungen A1, A2, A3, A4 und A5 steht, Groups A 1 , A 2 , A 3 , A 4 and A 5 ,
R8, R9, R10, R1 1, R12, R13, R14, R15, R16, R17, R18 und R19 unabhängig R 8, R 9, R 10, R 1 1, R 12, R 13, R 14, R 15, R 16, R 17, R 18 and R 19 are independently
voneinander für Wasserstoff, Fluor, Chlor, Brom, lod, (Ci-C6)-Alkyl,  each other for hydrogen, fluorine, chlorine, bromine, iodine, (C 1 -C 6) -alkyl,
(C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (Ci-C6)-Haloalkyl, (C2-C6)-Haloalkenyl, (C2-C6)-Haloalkinyl, (C3-C6)-Cycloalkyl, Aryl, Aryl-(Ci-C6)-alkyl, (C2-C6) alkenyl, (C2-C6) -alkynyl, (Ci-C 6) -haloalkyl, (C2-C6) haloalkenyl, (C2-C6) haloalkynyl, (C3-C6 ) -Cycloalkyl, aryl, aryl- (C 1 -C 6 ) -alkyl,
Heteroaryl , Heteroaryl-(Ci -C6)-al kyl , (C3-C6)-Cycloal kyl-(Ci -C6)-al kyl , Heterocyclyl , Heterocyclyl-(Ci -C6)-al kyl , (Ci -C6)-Al koxy-(Ci -C6)-al kyl , (Ci-C6)-Alkylthio-(Ci-C6)-alkyl, (Ci-C6)-Haloalkoxy-(Ci-C6)-alkyl, (Ci-C6)- Haloalkylthio-(Ci-C6)-alkyl, COOR23 stehen, Heteroaryl, heteroaryl (Ci-C6) -alkyl, (C 3 -C 6) -Cycloal alkyl- (Ci-C6) -alkyl, heterocyclyl, heterocyclyl (Ci-C6) -alkyl, ( Ci -C 6) -alkyl alkoxy- (Ci-C6) -alkyl, (Ci-C6) alkylthio (Ci-C 6) alkyl, (Ci-C6) haloalkoxy (Ci-C 6) alkyl, (C 1 -C 6 ) -haloalkylthio (C 1 -C 6 ) -alkyl, COOR 23 ,
R5 und R6 mit dem Atom, an das sie gebunden sind, einen vollständig R 5 and R 6 with the atom to which they are attached, a complete
gesättigten, oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5-7-gliedrigen Ring bilden,  form saturated, or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring,
R20 für Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (Ci-C6)- Haloalkyl, (C2-C6)-Haloalkenyl, (C2-C6)-Haloalkinyl, (C3-C6)-Cycloalkyl, (C4-C6)-Cycloalkenyl, (Ci-C6)-Alkoxy, Aryl, Heteroaryl, Heterocyclyl, R 20 is hydrogen, (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) -alkynyl, (Ci-C 6) - haloalkyl, (C2-C6) - haloalkenyl, (C2-C6) haloalkynyl, (C3-C6) -cycloalkyl, (C 4 -C 6) cycloalkenyl, (Ci-C6) alkoxy, aryl, heteroaryl, heterocyclyl,
(Ci-C6)-Alkylcarbonyl, Aryl-(Ci-C6)-Alkylcarbonyl, (C3-C6)- Cycloalkylcarbonyl, Arylcarbonyl, Heteroarylcarbonyl, (C1-C6)- Alkoxycarbonyl, (C2-C6)-Alkenyloxycarbonyl, Aryl-(Ci-C6)-alkoxycarbonyl, Heteroaryl-(Ci-C6)-alkoxycarbonyl, (C3-C6)-Cycloalkyl-(Ci-C6)- alkoxycarbonyl, (Ci-C6)-Alkylsulfonyl, (Ci-C6)-Haloalkylsulfonyl, (Ci-C 6) alkylcarbonyl, aryl (Ci-C 6) alkylcarbonyl, (C 3 -C 6) - cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, (C1-C6) - alkoxycarbonyl, (C2-C6) alkenyloxycarbonyl, Aryl- (C 1 -C 6) -alkoxycarbonyl, heteroaryl- (C 1 -C 6) -alkoxycarbonyl, (C 3 -C 6) -cycloalkyl- (C 1 -C 6) -alkoxycarbonyl, (C 1 -C 6) -alkylsulphonyl, (C 1 -C 6) - haloalkylsulfonyl,
Arylsulfonyl, Heteroarylsulfonyl, (C3-C6)-Cycloalkylsulfonyl, (C1-C6)- Alkylsulfinyl, Arylsulfinyl, Heteroarylsulfinyl, (C3-C6)-Cycloalkylsulfinyl steht, n für 0, 1 oder 2 steht R21 und R22 gleich oder verschieden sind und unabhängig voneinander für Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (Ci-C6)- Cyanoalkyl, (Ci-C6)-Haloalkyl, (C2-C6)-Haloalkenyl, (C2-C6)-Haloalkinyl, (C3-C6)-Cycloalkyl, (C3-C6)-Halocycloalkyl, (C -C6)-Cycloalkenyl, (C -C6)- Halocycloalkenyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Haloalkoxy- (Ci-C6)-alkyl, (Ci -C6)-Al kylth io-(Ci -C6)-al kyl , (Ci-C6)-Haloalkylthio- (Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-haloalkyl, Aryl, Aryl-(Ci-C6)-alkyl, Heteroaryl, Heteroaryl-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (C4-C6)-Cycloalkenyl-(Ci-C6)-alkyl, COR23, SO2R24, -(Ci-C6)-Alkyl- HNO2S-, (C3-C6)-Cycloalkyl-HNO2S-, Heterocyclyl, (Ci-C6)- Alkoxycarbonyl-(Ci-C6)-alkyl, (Ci-C6)-Alkoxycarbonyl, Aryl-(Ci-Ce)- Alkoxycarbonyl-(Ci-C6)-alkyl, Aryl-(Ci-C6)-Alkoxycarbonyl, Heteroaryl- (Ci-C6)-Alkoxycarbonyl, (C2-C6)-Alkenyloxycarbonyl, (C2-C6)- Alkinyloxycarbonyl, Heterocyclyl-(Ci-C6)-alkyl stehen Arylsulfonyl, heteroarylsulfonyl, (C 3 -C 6) -cycloalkylsulfonyl, (C 1 -C 6) -alkylsulfinyl, arylsulfinyl, heteroarylsulfinyl, (C 3 -C 6) -cycloalkylsulfinyl, n is 0, 1 or 2 R 21 and R 22 are identical or different and are each independently hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (C 1 -C 6 ) -cyanoalkyl , (Ci-C 6) -haloalkyl, (C2-C6) haloalkenyl, (C2-C6) haloalkynyl, (C3-C6) -cycloalkyl, (C3-C 6) halocycloalkyl, (C -C 6) -cycloalkenyl, (C-C6) - Halocycloalkenyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, (Ci-C 6) haloalkoxy (Ci-C 6) alkyl, ( Ci -C 6) -alkyl kylth io- (Ci-C6) -alkyl, (Ci-C 6) -Haloalkylthio- (Ci-C 6) alkyl, (Ci-C6) alkoxy (Ci-C 6 ) -haloalkyl, aryl, aryl- (C 1 -C 6 ) -alkyl, heteroaryl, heteroaryl- (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 4 -C 6) cycloalkenyl (Ci-C 6) alkyl, COR 23, SO 2 R 24, - (Ci-C 6) alkyl HNO2S-, (C3-C6) -cycloalkyl-HNO 2 S , Heterocyclyl, (C 1 -C 6 ) -alkoxycarbonyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxycarbonyl, aryl- (C 1 -C 6 ) -alkoxycarbonyl- (C 1 -C 6 ) -alkyl, aryl- (Ci -C6) alkoxycarbonyl, heteroaryl- (C 1 -C 6) -alkoxycarbonyl, (C 2 -C 6) -alkenyloxycarbonyl, (C 2 -C 6) -alkynyloxycarbonyl, hetero cyclyl (Ci-C6) alkyl
R23 für Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (Ci-C6)- Cyanoalkyl, (Ci-C6)-Haloalkyl, (C2-C6)-Haloalkenyl, (C2-C6)-Haloalkinyl, (C3-C6)-Cycloalkyl, (C3-C6)-Halocycloalkyl, (C -C6)-Cycloalkenyl, (C -C6)- Halocycloalkenyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)- haloalkyl, Aryl, Aryl-(Ci-C6)-alkyl, Heteroaryl, Heteroaryl-(Ci-C6)-alkyl, (C3-C6)-Cycloal kyl-(Ci -C6)-al kyl , (C -C6)-Cycloal kenyl-(Ci -C6)-alkyl , (C1 -C6)-Al koxycarbonyl-(Ci -C6)-al kyl , (C2-C6)-Al kenyloxycarbonyl-(Ci -C6) alkyl, Aryl-(Ci-C6)-Alkoxycarbonyl-(Ci-C6)-alkyl, Hydroxycarbonyl-(Ci-C6) alkyl, Heterocyclyl, Heterocyclyl-(Ci-C6)-alkyl steht und R 23 is hydrogen, (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) -alkynyl, (Ci-C 6) - cyanoalkyl, (Ci-C 6) - haloalkyl, (C2-C6) haloalkenyl, (C2-C6) haloalkynyl, (C3-C6) -cycloalkyl, (C3-C 6) halocycloalkyl, (C-C6) cycloalkenyl, (C - C 6 ) - halocycloalkenyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -haloalkyl, aryl, aryl- (C 1 -C 6 ) - alkyl, heteroaryl, heteroaryl (Ci-C6) alkyl, (C 3 -C 6) -Cycloal alkyl- (Ci-C6) -alkyl, (C-C6) -Cycloal kenyl- (Ci-C6 ) -alkyl, (C 1 -C 6) -alkoxycarbonyl- (C 1 -C 6) -alkyl, (C 2 -C 6) -alkhenyloxycarbonyl- (C 1 -C 6) -alkyl, aryl- (C 1 -C 6) -alkoxycarbonyl- (Ci -C 6) -alkyl, hydroxycarbonyl- (C 1 -C 6) -alkyl, heterocyclyl, heterocyclyl- (C 1 -C 6) -alkyl and
R24 für Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (Ci-C6)- Cyanoalkyl, (Ci-C6)-Haloalkyl, (C2-C6)-Haloalkenyl, (C2-C6)-Haloalkinyl, (C3-C6)-Cycloalkyl, (C3-C6)-Halocycloalkyl, (C -C6)-Cycloalkenyl, (C -C6)- Halocycloalkenyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)- haloalkyl, Aryl, Aryl-(Ci-C6)-alkyl, Heteroaryl, Heteroaryl-(Ci-C6)-alkyl, Heterocyclyl-(Ci -C6)-alkyl , (C3-C6)-Cycloal kyl-(Ci -C6)-al kyl , (C -C6)- Cycloalkenyl-(Ci-C6)-alkyl, NR21 R22 steht. Verwendung einer oder mehrerer Verbindungen der Formel (I) oder deren Salze gemäß einem der Ansprüche 1 bis 3 zur Toleranzerhöhung gegenüber abiotischem Stress in Pflanzen. R 24 is hydrogen, (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) -alkynyl, (Ci-C 6) - cyanoalkyl, (Ci-C 6) - haloalkyl, (C2-C6) haloalkenyl, (C2-C6) haloalkynyl, (C3-C6) -cycloalkyl, (C3-C 6) halocycloalkyl, (C-C6) cycloalkenyl, (C - C 6 ) - halocycloalkenyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -haloalkyl, aryl, aryl- (C 1 -C 6 ) - alkyl, heteroaryl, heteroaryl (Ci-C6) alkyl, heterocyclyl (Ci-C6) alkyl, (C 3 -C 6) -Cycloal alkyl- (Ci-C6) -alkyl, (C -C 6 ) - cycloalkenyl- (C 1 -C 6 ) -alkyl, NR 21 R 22 . Use of one or more compounds of the formula (I) or salts thereof according to one of Claims 1 to 3 for increasing the tolerance to abiotic stress in plants.
Behandlung von Pflanzen, umfassend die Applikation einer zur Steigerung der Widerstandsfähigkeit von Pflanzen gegenüber abiotischen Stressfaktoren wirksamen, nicht-toxischen Menge einer oder mehrerer Verbindungen der allgemeinen Formel (I) oder deren Salze gemäß einem der Ansprüche 1 bis 3. Treatment of plants comprising the application of a non-toxic amount of one or more compounds of the general formula (I) or salts thereof according to one of Claims 1 to 3 which is effective for increasing the resistance of plants to abiotic stress factors.
Behandlung gemäß Anspruch 5, wobei die abiotischen Streßbedingungen einer oder mehrer Bedingungen ausgewählt aus der Gruppe von Hitze, Dürre, Kälte- und Trockenstress, osmotischer Streß, Staunässe, erhöhter Bodensalzgehalt, erhöhtes Ausgesetztsein an Mineralien, Ozonbedingungen, A treatment according to claim 5, wherein the abiotic stress conditions include one or more conditions selected from the group consisting of heat, drought, cold and dry stress, osmotic stress, waterlogging, increased soil salinity, increased exposure to minerals, ozone conditions,
Starklichtbedingungen, beschränkte Verfügbarkeit von Stickstoffnährstoffen, beschränkte Verfügbarkeit von Phosphornährstoffen entsprechen. High light conditions, limited availability of nitrogen nutrients, limited availability of phosphorus nutrients.
Verwendung einer oder mehrerer Verbindungen der allgemeinen Formel (I) oder deren Salze gemäß einem der Ansprüche 1 bis 3 in der Sprühapplikation auf Pflanzen und Pflanzenteilen in Kombinationen mit einem oder mehrer Use of one or more compounds of the general formula (I) or salts thereof according to any one of claims 1 to 3 in the spray application to plants and plant parts in combinations with one or more
Wirkstoffen ausgewählt aud der Gruppe der Insektizide, Lockstoffe, Akarizide, Fungizide, Nematizide, Herbizide, wachstumsregulatorische Stoffe, Safener, die Pflanzenreife beeinflussende Stoffe und Bakterizide. Active ingredients selected from the group of insecticides, attractants, acaricides, fungicides, nematicides, herbicides, growth regulators, safeners, plant maturity affecting substances and bactericides.
Verwendung einer oder mehrerer der Verbindungen der allgemeinen Formel (I) oder deren Salze gemäß einem der Ansprüche 1 bis 3 in der Sprühapplikation auf Pflanzen und Pflanzenteilen in Kombinationen mit Düngemitteln. Use of one or more of the compounds of general formula (I) or salts thereof according to one of Claims 1 to 3 in the spray application on plants and plant parts in combinations with fertilizers.
Verwendung einer oder meherer der Verbindungen der allgemeinen Formel (I) oder deren Salze gemäß einem der Ansprüche 1 bis 3 zur Applikation auf gentechnisch veränderten Sorten, deren Saatgut, oder auf Anbauflächen auf denen diese Sorten wachsen. Use of one or more of the compounds of the general formula (I) or salts thereof according to one of claims 1 to 3 for application to genetically modified varieties, their seed, or on cultivated areas on which these varieties grow.
10. Sprühlösung zur Behandlung von Pflanzen, enthaltend eine zur Steigerung der Widerstandsfähigkeit von Pflanzen gegenüber abiotischen Stressfaktoren wirksame Menge einer oder meherer Verbindungen der allgemeinen Formel (I) gemäß einem der Ansprüche 1 bis 3 oder deren Salze. 10. A spray solution for the treatment of plants, comprising an effective for increasing the resistance of plants to abiotic stress factors amount of one or more compounds of general formula (I) according to any one of claims 1 to 3 or salts thereof.
1 1 . Verwendung von Sprühlösungen, die eine oder mehrere der Verbindungen der allgemeinen Formel (I) gemäß einem der Ansprüche 1 bis 3 oder deren Salze enthalten, zur Steigerung der Widerstandsfähigkeit von Pflanzen gegenüber abiotischen Stressfaktoren. 1 1. Use of spray solutions containing one or more of the compounds of the general formula (I) according to any one of claims 1 to 3 or salts thereof for increasing the resistance of plants to abiotic stress factors.
12. Verfahren zur Erhöhung der Stresstoleranz bei Pflanzen ausgewählt aus der Gruppe der Nutzpflanzen, Zierpflanzen, Rasenarten, oder Bäumen, welches die Applikation einer ausreichenden, nicht-toxischen Menge einer oder mehrere Verbindungen der allgemeinen Formel (I) gemäß einem der Ansprüche 1 bis 3 oder deren Salze auf die Fläche, wo die entsprechende Wirkung gewünscht wird, umfasst, wobei die Applikation auf die Pflanzen, deren Saatgut oder auf die Fläche, auf der die Pflanzen wachsen, erfolgt. 12. A method for increasing the stress tolerance in plants selected from the group of useful plants, ornamental plants, lawn species, or trees, which comprises applying a sufficient, non-toxic amount of one or more compounds of the general formula (I) according to one of claims 1 to 3 or their salts on the area where the corresponding effect is desired, wherein the application is carried out on the plants, their seeds or on the surface on which the plants grow.
13. Verfahren gemäß Anspruch 12, wobei die Widerstandsfähigkeit der so 13. The method according to claim 12, wherein the resistance of the so
behandelten Pflanzen gegenüber abiotischem Stress gegenüber nicht behandelten Pflanzen unter ansonsten gleichen physiologischen Bedingungen um mindestens 3% erhöht ist.  treated plants is increased by at least 3% against abiotic stress compared to untreated plants under otherwise identical physiological conditions.
EP16741278.2A 2015-07-17 2016-07-14 Substituted heteroaryl carboxylic acid hydrazides or salts thereof and use thereof to increase stress tolerance in plants Withdrawn EP3325467A1 (en)

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