EP1173449A1 - Phosphoric benzoyl derivatives and their use as herbicides - Google Patents

Phosphoric benzoyl derivatives and their use as herbicides

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Publication number
EP1173449A1
EP1173449A1 EP00922650A EP00922650A EP1173449A1 EP 1173449 A1 EP1173449 A1 EP 1173449A1 EP 00922650 A EP00922650 A EP 00922650A EP 00922650 A EP00922650 A EP 00922650A EP 1173449 A1 EP1173449 A1 EP 1173449A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
alkoxy
formula
cyano
haloalkyl
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Withdrawn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
EP00922650A
Other languages
German (de)
French (fr)
Inventor
Klaus Langemann
Thorsten Volk
Ernst Baumann
Wolfgang Von Deyn
Steffen Kudis
Guido Mayer
Ulf Misslitz
Ulf Neidlein
Matthias Witschel
Martina Otten
Karl-Otto Westphalen
Helmut Walter
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.)
BASF SE
Original Assignee
BASF SE
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Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP1173449A1 publication Critical patent/EP1173449A1/en
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6568—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms
    • C07F9/65685—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms the ring phosphorus atom being part of a phosphine oxide or thioxide
    • 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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
    • A01N57/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing aromatic radicals
    • 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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
    • A01N57/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing heterocyclic radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4021—Esters of aromatic acids (P-C aromatic linkage)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4025—Esters of poly(thio)phosphonic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/44—Amides thereof
    • C07F9/4403—Amides thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4419—Amides of aromatic acids (P-C aromatic linkage)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
    • C07F9/5325—Aromatic phosphine oxides or thioxides (P-C aromatic linkage)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
    • C07F9/5329—Polyphosphine oxides or thioxides
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/572—Five-membered rings
    • C—CHEMISTRY; METALLURGY
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
    • C07F9/6503—Five-membered rings
    • C07F9/65031—Five-membered rings having the nitrogen atoms in the positions 1 and 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6527—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07F9/653—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
    • C07F9/657163—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom
    • C07F9/657181—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and, at least, one ring oxygen atom being part of a (thio)phosphonic acid derivative
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6578—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and sulfur atoms with or without oxygen atoms, as ring hetero atoms
    • C07F9/65785—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and sulfur atoms with or without oxygen atoms, as ring hetero atoms the ring phosphorus atom and, at least, one ring sulfur atom being part of a thiophosphonic acid derivative

Definitions

  • the present invention relates to phosphorus-containing benzoyl derivatives of the formula I.
  • R 2 is hydrogen, -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, hydroxy, Ci-C ⁇ -alkoxy, C 3 -C 6 -alkenyloxy, C 3 - C 6 -alkynyloxy, mercapto, Ci-C ⁇ -alkylthio, C -C 6 -alkenylthio, C 3 -C 6 -alkynylthio, amino, Ci-C ⁇ -alkyla ino, di- (-C-C 6 -alkyl) amino, (Ci-C ⁇ -alkoxy) (Ci-C ⁇ -alkyl) -amino, (C 3 -Ce-alkenyl) (-C-C 6 -alkyl) amino,
  • alkyl, Alkenyl or alkynyl radicals can be partially or completely halogenated and / or can carry one to three of the following groups:
  • Phenyl or phenoxy which may be partially or fully halogenated and / or may carry one to three of the following groups: nitro, cyano, C 1 -C 4 -alkyl, C 4 haloalkyl,
  • R 1 and R 2 together form a -0- (CH) m -0-, -0- (CH) m -S-, -S- (CH 2 ) m -S-, -NR5- (CH 2 ) m -NR 5 -, -0- (CH 2 ) m -NR 5 -, -S- (CH 2 ) m -NR 5 -, - (CH 2 ) n -0-, - (CH 2 ) n -S- or
  • Halogen cyano, C 1 -C 4 -alkyl, C 4 haloalkyl,
  • R 1 and R 2 together form a - (CH) P chain, which can be interrupted by oxygen, sulfur or NR 5 and / or can carry one to three radicals from the following group:
  • Halogen, cyano, C 4 -alkyl, C 4 haloalkyl, C 1 -C 4 -alkoxy, C 4 -alkoxycarbonyl or phenyl which is substituted is un- or partially or completely halogenated and / or can carry up to three of the following groups:
  • R 3 is hydrogen, nitro, cyano, halogen, -CC 6 alkyl
  • Di- (C ⁇ -C6 alkyl) aminosulfonyl, (C ⁇ -C 6 -Alkylsulfo- nyl) amino, (Ci-C ß haloalkylsulfonyl) amino, N- (Ci-C ⁇ -alkyl) -N- (C ⁇ - C 6 -alkylsulfonyl) amino, N- (-C-C 6 -alkyl) -N- (Ci-C ß -halogenalkylsulfonyl) amino, -P ( X) R 1 R 2 , phenyl or heterocyclyl, the two the latter radicals can be partially or completely halogenated and / or can carry one to three of the following groups:
  • R 5 is hydrogen, Ci-C ß- alkyl, Ci-C ⁇ -haloalkyl or Ci -C 6 alkoxy;
  • Q is a radical of the formula Q 1 , Q 2 , Q 3 or Q 4
  • R 8 , R 10 , R 12 are hydrogen, Cx-C ⁇ - alkyl, -C-C 6 -alkoxy, C ⁇ -C 6 -alkylthio or C ⁇ -C 6 -alkoxycarbonyl;
  • R 7 and R 8 or R 9 and R 10 or R 11 and R 12 together form an -O- (CH 2 ) u -0-, -0- (CH 2 ) U -S-, -S- (CH 2 ) U -S-, -0- (CH 2 ) v - or -S- (CH) V chain, which can be substituted by one to three radicals from the following group:
  • R 7 and R 8 or R 9 and R 10 or R 11 and R 12 together form a - (CH 2 ) W chain which can be interrupted by oxygen or sulfur and / or be substituted by one to four radicals from the following group can: halogen, cyano, C 1 -C 4 alkyl, -C-C 4 haloalkyl or
  • R 7 and R 8 or R 9 and R 10 or R 11 and R 12 together form a methylidene group which can be substituted by one or two radicals from the following group: halogen, hydroxyl, formyl, cyano, Ci-C ⁇ - alkyl, -C-C 6 _ haloalkyl, Ci-C ⁇ - alkoxy, Ci-Cg-haloalkoxy, Ci-C ⁇ -alkylthio, Ci-C ⁇ -haloalkylthio, Ci-C ⁇ -alkylsulfinyl, Ci-Cg-haloalkylsulfinyl, Ci C ⁇ -alkyl-sulfonyl or Ci-C ß -haloalkylsulfonyl;
  • R 7 and R 9 or R 9 and R 11 or R 7 and R 11 together form a - (CH) V chain, which can be substituted by one to three radicals from the following group: halogen, -CC 6 alkyl, C ⁇ -C 6 alkoxy, hydroxy or
  • R 13 Ci-C ⁇ -alkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl,
  • Phenylaminocarbonyl or heterocyclylaminocarbonyl where the phenyl and heterocyclyl radicals of the last 8 substituents can be partially or completely halogenated and / or can carry one to three of the following radicals:
  • R 14 , R 15 , R 16 C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl, C 3 -C 6 cycloalkyl,
  • Ci-C ß -haloalkylamino di- (Ci-C ⁇ -alkyl) amino or di- (Ci-Cg-haloalkyl) amino, where the alkyl, cycloalkyl and alkoxy radicals mentioned can be partially or completely halogenated and / or can wear one to three of the following groups: Cyano, -C ⁇ C 4 alkoxy, C ⁇ ⁇ C 4 alkylthio, di- (C 1 -C 4 alkyl) amino, C ! -C 4 alkylcarbonyl or C; ⁇ .-C 4 alkoxycarbonyl;
  • Phenyl, heterocyclyl, phenoxy or heterocyclyloxy where the phenyl and heterocyclyl radicals of the latter substituents can be partially or completely halogenated and / or can carry one to three of the following radicals: nitro, cyano, C 1 -C 4 -alkyl, Cx ⁇ Haloalkyl,
  • R 17 Ci-C ⁇ alkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl,
  • alkyl, cycloalkyl and alkoxy radicals mentioned can be partially or completely halogenated and / or can carry one to three radicals from the following group: cyano, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio or
  • R 18 , R 19 C ⁇ - C 6 alkyl, C 3 -C 6 alkenyl, C 3 - C 6 alkynyl or
  • R 20 is a radical as mentioned under R 6 ;
  • R 21 is hydrogen, Ci-C ß- alkyl, -C-C 6 -haloalkyl, hydroxy, Ci-C ß -alkoxy or Ci-C ⁇ -haloalkoxy;
  • R 22 is hydrogen, halogen, -CC 6 -alkyl, Ci-C ⁇ -haloalkyl, hydroxy, Ci-C ⁇ -alkoxy, -C-C 6 -haloalkoxy, Ci-C ß -alkylthio or Ci-C ⁇ -haloalkylthio ;
  • R 23 are hydrogen, C 6 alkyl, Ci-C ö haloalkyl, C 3 -C 6 -Cy- cloalkyl or C 3 -C 6 halocycloalkyl;
  • R 24 is hydrogen, -CC 6 alkoxycarbonyl, -C-C 6 haloalkoxycarbonyl, hydroxycarbonyl or cyano;
  • the invention relates to processes and intermediates for the preparation of compounds of the formula I, compositions which contain them, and to the use of the compounds of the formula I and compositions for controlling pests.
  • Herbicidally active phosphorothionoamidates are known from the literature, for example from DE-A 22 60 705 and DE-A 21 66 729. No. 3,775,057 describes pyridinylphosphonates.
  • Substituted benzoyl isoxazoles or pyrazoles and substituted 2-phenyl-cyclohexane-1,3-diones or 1-phenyl-2-cyanoalkane-1,3-diones are likewise, for example from EP-A 418 175, EP-A 609 797, Wo 96/26 192, WO 96/26 206, EP-A 203 428, US 4,780,127, EP-A 315 075 and EP-A 625 505.
  • herbicidal compositions which contain the compounds I and have a very good herbicidal action.
  • processes for the preparation of these compositions and processes for controlling unwanted vegetation using the compounds I have been found.
  • the compounds of the formula I can contain one or more centers of chirality and are then present as enantiomers or mixtures of diastereomers.
  • the invention relates both to the pure enantiomers or diastereomers and to their mixtures.
  • the compounds of the formula I can also be present in the form of their agriculturally useful salts, the type of salt generally not being important. In general, the salts of those cations or the acid addition salts of those acids whose cations or anions do not adversely affect the herbicidal activity of the compounds I
  • the cations used are, in particular, ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium and magnesium, and of the transition metals, preferably manganese, copper, zinc and iron, and ammonium, where if desired one to four hydrogen atoms by C ⁇ - C 4 alkyl, hydroxy-C ⁇ -C 4 alkyl, C 1 -C 4 alkoxy -CC-C 4 alkyl, hydroxy-Ci -C 4 alkoxy-C 1 -C 4 alkyl, phenyl or Benzyl can be replaced, preferably ammonium, dimethylammonium, diisopropylammonium, tetramethylammonium, tetrabutylammonium, 2- (2-hydroxyeth-1-oxy) eth-1-ylammonium, di (2-hydroxyeth-1-yl) ammonium, trimethylbenzylammonium , further phosphonium ions, sul
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of C 1 -C 4 -alkanoic acids, preferably formate, acylate , Propionate and butyra.
  • -C -C alkyl e.g. Methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl or 1, 1-dimethylethyl;
  • Ci-C ⁇ - alkyl and the alkyl parts of -CC 6 -alkylcarbonyl -CC-C 6 - alkyl, -C-C 6 -alkoxyimino -CC-C 6 alkyl, N- (C 3 -C 6 - Alkenyl) -N- (-C-C 6 -alkyl) -amino, N- (C 3 -C 6 -alkynyl) -N- (Ci-C ⁇ -alkyl) -amino, phenyl-Ci-C ⁇ -alkyl , N- (C ⁇ -C 6 -Al- kyl) -N- (C 3 -C 6 alkylsulfonyl) amino, N- (C ⁇ -C6 alkyl) -N- (C ⁇ -C 6 - haloalkylsulfonyl) -amino, heterocyclyl-Ci-C
  • C ⁇ -C 4 alkyl as mentioned above, and for example pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2, 2-dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1-dimethylpropyl, 1,2 -Dirne - thylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl,
  • C ⁇ -C haloalkyl a C ⁇ ⁇ 4 -alkyl radical, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl , Dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2, 2-difluoroethyl, 2, 2, 2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2 , 2-difluoroethyl, 2, 2-dichloro-2-fluoroethyl, 2, 2, 2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl
  • Ci-C ß -haloalkyl and the haloalkyl parts of C ⁇ -C 6 -haloalkylamino, di - (C ⁇ -C 6 -haloalkyl) amino: C ⁇ -C 4 ⁇ haloalkyl, as mentioned above, and for example 5-fluoropentyl , 5-chloropentyl, 5-bromopentyl, 5-iodopentyl, undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-iodohexyl or do- decafluorhexyl;
  • -C-C 4 alkoxy for example methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1, 1-dimethylethoxy;
  • C 1 -C 6 -alkoxy and the alkoxy parts of di- (C 1 -C 6 -alkoxy) methyl, (C 1 -C 6 -alkoxy) (C 1 -C 6 -alkylthio) methyl, Ci-C ⁇ -alkoxy- imino- Ci-C ⁇ -alkyl and N- (C ⁇ -C 6 -alkoxy) -N- (-C-C 6 -alkyl) -amino: C ⁇ -C 4 ⁇ alkoxy, as mentioned above, and for example pentoxy,
  • C ⁇ -C 4 -haloalkoxy a C ⁇ -C4-alkoxy as mentioned above, the, chlorine, bromine / iodine or partially or completely substituted by fluorine and is substituted, eg fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, Bromdi - fluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromomethoxy, 2-iodoethoxy, 2, 2-difluoroethoxy, 2, 2, 2-trifluoroethoxy,
  • 2-chloro-2-fluoroethoxy 2-chloro-2, 2-difluoroethoxy, 2,2-di-chloro-2-fluoroethoxy, 2, 2, 2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2- Chloropropoxy, 3-chloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 2, 2-difluoropropoxy, 2, 3-difluoropropoxy, 2, 3-dichloropropoxy, 3, 3, 3-trifluoropropoxy, 3, 3, 3-trichloropropoxy, 2,2, 3, 3, 3-pentafluoropropoxy, heptafluoropropoxy, 1- (fluoromethyl) -2-fluoroethoxy, 1- (chloromethyl) -2-chloroethoxy, 1- (bromomethyl) -2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or non
  • C 1 -C 4 -Alkylthio for example methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio or 1, 1-dimethylethylthio;
  • Ci-C ß -Alkylthio and the alkylthio parts of C ⁇ -C 6 -alkyl-thio-Ci-C ⁇ - alkyl, di- (-C-C 6 alkylthio) methyl and (-C-C 6 alkoxy) - (C ⁇ -C 6 -alkylthio) methyl: -C-C 4 alkylthio, as mentioned above, and for example pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2, 2-dimethylpropylthio, 1-ethylpropylthio, hexylthio , 1, 1-dimethylpropyl ⁇ thio, 1, 2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1, 1-dimethylbutylthio, 1, 2-dimethylbut
  • Ci-C ⁇ -haloalkylthio a Ci-C ⁇ -alkylthio radical, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio , 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2, 2, 2-trifluoroethylthio, 2,2,2-trichloroethylthio, 2-chloro-2-fluoroethylthio, 2 -Chlor-2, 2-di-fluoroethylthio, 2, 2-dichloro-2-fluoroethylthio, pentafluoroe
  • methylsulfinyl ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl or 1, 1-dimethylethylsulfinyl ;
  • Ci-C ⁇ -haloalkylsulfinyl Ci-C ⁇ -alkylsulfinyl radical, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example fluoromethylsulfinyl, difluoromethylsulfinyl, trifluoromethylsulfinyl, chlorodifluoromethylsulfinyl, bromodifluoromethylsulfonyl 2-fluoroethylsulfinyl, 2-chloroethylsulfinyl, 2-bromoethylsulfinyl, 2-iodoethylsulfinyl, 2,2-difluoroethylsulfinyl, 2,2, 2-trifluoroethylsulfinyl, 2,2, 2-trichloroethylsulfinyl, 2-chloro-2-fluoroe
  • methylsulfonyl ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl or 1 , 1-dimethylethylsulfonyl;
  • Ci-C ⁇ -alkylsulfonyl and the alkylsulfonyl radicals of C ⁇ -C 6 -alkylsulfonyl-C ⁇ -C 6 -alkyl, C ⁇ -C 6 -alkylsulfonyl -amino and N- (-C ⁇ -C 6 alkyl) -N- (C ⁇ -C 6- alkylsulfonyl) amino: -CC 4 -alkylsulfonyl as mentioned above, and pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1, 1-dimethylpropylsulfonyl, 1, 2-dimethylpropylsulfonyl -Dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylp
  • Ci-C ⁇ -haloalkylsulfonyl and the haloalkyl residues of N- (C ⁇ -C 6 -haloalkylsulfonyl) -amino and N- (Cx-C ⁇ -alkyl) -N- (Ci-C ⁇ -haloalkylsulfonyl) -amino: a C ⁇ - C 6 -alkylsulfonyl radical, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example fluoromethylsulfonyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethyl-2-sulfonyl, 2-fluorosulfonyl Chloroethylsulfonyl,
  • 2-bromoethylsulfonyl 2-iodoethylsulfonyl, 2, 2-difluoroethylsulfonyl, 2, 2, 2-trifluoroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl, 2-chloro-2,2-difluoroethylsulfonyl, 2, 2-dichloro- 2-fluoroethylsulfonyl, 2, 2, 2-trichloroethylsulfonyl, pentafluoroethylsulfonyl, 2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl,
  • Ci-C ⁇ - alkylamino and the alkylamino residues of (Ci-C ß -alkoxy) (-C-C 6 -alkyl) amino, for example methylamino, ethylamino, propylamino, 1-methylethylamino, butylamino, 1-methylpropylamino, 2 -Methylpropylamino, 1, 1-dimethylethylamino, pentylamino, 1-methylbutylamino, 2-methylbutylamino, 3-methylbutylamino, 2, 2-dimethylpropylamino, 1-ethylpropylamino, hexylamino, 1, 1-dimethylpropylamino, 1, 2 -Dimethylpropylamino, 1-methylpentylamino, 2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino, 1, 1-dimethylbutylamino, 1, 2-di
  • (-C-C 6 -Alkylamino) sulfonyl for example methylaminosulfonyl, ethyl-aminosulfonyl, propylaminosulfonyl, 1-methylethylaminosulfonyl, butylaminosulfonyl, 1-methylpropylaminosulfonyl, 2-methylpropylaminosulfonyl, 1, 1-dimethylethylaminosulfonyl, 2-methyl-aminosulfonyl, methyl , 3-Methylbutylaminosulfonyl, 2, 2-Dimethylpropylaminosulfonyl, 1-Ethylpropylaminosulfonyl, Hexylaminosulfonyl, 1, 1-Dimethylpropylaminosulfonyl, 1,2-Dirnethylpro- pylaminosulfonyl, 1-Methylpentylaminosulf
  • Di- (-C 6 -alkyl) -aminosulfonyl for example N, N-dimethylaminosulfonyl, N, N-diethylaminosulfonyl, N, N-di- (1-methylethyl) aminosulfonyl, N, N-dipropylaminosulfonyl, N , N-Dibutylaminosulfonyl, N, N-Di- (1-methylpropyl) -aminosulfonyl, N, N-Di- (2-methyl-propyl) -aminosulfonyl, N, N-Di- (1, 1-dimethylethyl) -aminosulfonyl, N-ethyl-N-methylaminosulfonyl, N-methyl-N-propylaminosulfonyl, N-methyl-N- (1-methylethyl) -aminosulfonyl, N-butyl-
  • Di- (-C 4 ⁇ alkyl) amino, and the dialkylamino residues of di- (-C 4 ⁇ alkyl) amino -CC-C 4 -alkoxycarbonyl so for example N, N-dimethylamino, N, N-diethylamino , N, N-dipropylamino, N, N-di- (1-methylethyl) amino, N, N-dibutylamino, N, N-di- (1-methylpropyl) amino, N, N-di- (2-methylpropyl ) amino, N, N-di- (1, 1-dimethylethyl) amino, N-ethyl-N-methylamino, N-methyl-N-propylamino, N-methyl-N- (1-methylethyl) amino, N- Butyl-N-methylamino, N-methyl-N- (1-methylpropyl) amino, N-methyl-N- (2-methylpropyl)
  • Di- (-C 6 -alkyl) amino di- (-C 4 -alkyl) amino as mentioned above, and N, N-dipentylamino, N, N-dihexylamino, N-methyl-N-pentylamino, N- Ethyl -N-pentylamino, N-methyl -N-hexylamino or N-ethyl-N-hexylamino.
  • C 1 -C 4 ⁇ alkylcarbonyl for example methylcarbonyl, ethylcarbonyl, propylcarbonyl, 1-methylethylcarbonyl, butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl or 1, 1-dimethylethylcarbonyl; Ci-C ⁇ -alkylcarbonyl, and the alkylcarbonyl radicals of -CC 6 -alkylcarbonyl -CC-C 6 -alkyl: -C-C 4 -alkylcarbonyl, as mentioned above, and for example pentylcarbonyl, 1-methylbutylcarbonyl, 2-methylbutylcarbonyl, 3rd -Methylbutylcarbonyl, 2,2-dimethylpropylcarbonyl, 1-ethylpropylcarbonyl, hexylcarbonyl, 1, 1-dimethylpropylcarbonyl, 1, 2-dimethylpropylcarbonyl,
  • C 1 -C 2 -alkylcarbonyl C ⁇ -C 6 -alkylcarbonyl, as mentioned above, and heptylcarbonyl, octylcarbonyl, pentadecylcarbonyl or heptadecylcarbonyl;
  • haloalkylcarbonyl a Ci-Cg-alkylcarbonyl radical, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example chloroacetyl, dichloroacetyl, trichloroacetyl, fluoroacetyl, difluoroacetyl, trifluoroacetyl, Chlorofluoroacetyl, dichlorofluoroacetyl, chlorodifluoroacetyl, 2-fluoroethylcarbonyl,
  • Di- (-C 4 ⁇ alkyl) amino -C -C 4 alkoxycarbonyl that is, for example, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, 1-methylethoxy carbonyl, butoxycarbonyl, 1-methylpropoxycarbonyl, 2-methylpropoxycarbonyl or 1, 1-dimethylethoxycarbonyl;
  • Ci-C ⁇ alkoxy carbonyl (Ci-C ⁇ alkoxy) carbonyl; and Alkoxycarbonylmaschine of Ci-C ⁇ -alkoxycarbonyloxy (C ⁇ -C -alkoxy) carbonyl as mentioned vorste ⁇ starting, as well as, for example, pentoxycarbonyl, 1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 2,2-dimethylpropoxycarbonyl, 1 -Ethylpropoxycarbonyl, hexoxycarbonyl, 1, 1-dimethylpropoxycarbonyl, 1, 2-dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1,1-dimethylbutoxycarbonyl, 1, 2-dimethylbutoxycarbonyl , 1, 3-dimethylbutoxycarbonyl, 2, 2-dimethylbutoxycarbonyl, 2, 3-dimethylbut - oxycarbon
  • C 1 -C 6 -haloalkoxycarbonyl a C 1 -C 4 -alkoxycarbonyl radical, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example fluoromethoxycarbonyl, difluoromethoxycarbonyl, trifluoromethoxycarbonyl, chlorodifluoromethoxycarbonyl, bromodifluoromethoxy 2-fluoroethoxycarbonyl, 2-chloroethoxycarbonyl, 2-bromoethoxycarbonyl, 2-iodoethoxycarbonyl, 2,2-di-fluoroethoxycarbonyl, 2, 2, 2-trifluoroethoxycarbonyl, 2-chloro-2-fluoroethoxycarbonyl, 2-chloro-2, 2- difluoroethoxycarbonyl, 2, 2-dichloro-2-fluoroethoxycarbonyl, 2,2, 2-trichloroethoxycarbony
  • (C 1 -C 4 -alkylamino) carbonyl for example methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl, 1-methylethylaminocarbonyl, butylaminocarbonyl, 1-methylpropylaminocarbonyl, 2-methylpropylaminocarbonyl or 1, 1-dimethylethylaminocarbonyl;
  • (Ci-C ⁇ - alkylamino) carbonyl (-C-C 4 -alkylamino) carbonyl, as mentioned above, and for example pentylaminocarbonyl, 1-methyl'-butylaminocarbonyl, 2-methylbutylaminocarbonyl, 3-methylbutylaminocarbonyl, 2, 2-dimethylpropylaminocarbonyl, 1-ethyl propylaminocarbonyl, hexylaminocarbonyl, 1, 1-dimethylpropylaminocarbonyl, 1, 2-dimethylpropylaminocarbonyl, 1-methylpentylaminocarbonyl, 2-methylpentylaminocarbonyl, 3-methylpentylaminocarbonyl, 4-methylpentylaminocarbonyl, 1,1-dimethyl , 2-Dimethylbutylaminocarbonyl, 1, 3-Dimethylbutylaminocarbonyl, 2, 2-Dimethylbutylaminocarbonyl, 2, 3-D
  • Di- (C ⁇ -C 4 -alkyl) -aminocarbonyl for example N, N-dimethylaminocarbonyl, N, N-diethylaminocarbonyl, N, N-di- (1-methylethyl) aminocarbonyl, N, N-dipropylaminocarbonyl, N, N -Dibutylaminocarbonyl, N, N-di- (1-methylpropyl) -aminocarbonyl, N, N-di- (2-methylpropyl) -aminocarbonyl, N, N-di- (1, 1-dimethylethyl) -aminocarbo - nyl, N-ethyl-N-methylaminocarbonyl, N-methyl-N-propylamino-carbonyl, N-methyl-N- (1-methylethyl) -aminocarbonyl, N-butyl-N-methylaminocarbonyl,
  • C 3 -C 6 alkenyl and the alkenyl parts of C 3 -C 6 alkenyl carbonyl, C 3 -C 6 alkenyloxy, C 3 -C 6 alkenylthio, N- (C 3 -C 6 alkenyl) - N- (-C-C 6 ) alkylamino and di (C 3 -C 6 -alkenyl) amino: for example prop-2-en-1-yl, but-1-en-4-yl, 1-methyl-prop -2-en-l-yl, 2-methyl-prop-2-en-l-yl, 2-butene-l-yl, l-penten-3-yl, l-penten-4-yl, 2-pentene -4-yl, 1-methyl-but-2-en-l-yl, 2-methyl-but-2-en-l-yl, 3-methyl-but-2-en-l-yl, l-methyl -but-3-en-l-yl, 2-methyl-but-3-
  • C 3 -C 6 haloalkenyl a C 3 -Cg alkenyl radical, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example 2-chloroallyl, 3-chloroallyl, 2, 3 -Dichlorallyl, 3, 3-dichlorallyl, 2,3,3-trichlorallyl, 2,3-dichlorobut-2-enyl, 2-bromoallyl, 3-bromoallyl, 2, 3-dibromoallyl, 3, 3-dibromoallyl, 2 , 3, 3-tribromoallyl or 2,3-dibromobut-2-enyl;
  • C 3 -C 6 alkynyl and the alkynyl parts of C 3 -C 6 alkynylcarbonyl, C 3 -C 6 alkynyloxy, C 3 -C 6 alkynylthio, N- (C 3 -C 6 -A1- kynyl ) -N- (Ci-C ⁇ - alkyl) -amino and di (C 3 -C 6 -alkynyl) amino: for example propargyl, but-l-in-3-yl, but-l-in-4-yl, But-2-in-l-yl, Pent-1-in-3-yl, Pent-1-in-4-yl, Pent-1-in-5-yl, Pent-2-in-1-yl, Pent-2-in-4-yl, Pent-2-in-5-yl, 3-methyl-but-l-in-3-yl, 3-methyl-but-l-in-4-yl, hex-l-in-3
  • C 2 -C 6 alkynyl and the alkynyl parts of C 2 -C 6 alkynylcarbonyl: C 3 -C 6 alkynyl, as mentioned above, and ethynyl;
  • C 3 -C 6 haloalkynyl a C 3 -C 6 alkynyl radical, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example 1,1-difluoroprop-2- in-l-yl, 3-iodo-prop-2-in-l-yl, 4-fluorobut-2-in-l-yl, 4-chlorobut-2-in-l-yl, 1, 1-difluorobut- 2-in-l-yl, 4-iodobut-3-in-l-yl, 5-fluoropent-3-in-l-yl, 5-iodo-pent-4-in-l-yl, 6- Fluoro-hex-4-in-1-yl or 6-iodo-hex-5-in-1-yl;
  • C 3 -C 6 ⁇ cycloalkyl and the cycloalkyl parts of C 3 -C 6 cycloalkylcarbonyl: for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;
  • C 3 -C 6 halocycloalkyl a C 3 -C 6 cycloalkyl radical, as above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example 2,2-dichlorocycloprop-1-yl , 2, 2-difluorocycloprop-1-yl, 3 -chlorocyclopent-1-yl, 3-fluorocyclopent-1-yl, 3-bromocyclopent-1-yl, 3, 3 -dichlorocyclopent-1-yl, 3, 3 -Difluorocyclopent-1-yl, 4 -chlorocyclohex-1-yl, 4 -fluorocyclohex-1-yl, 4-bromocyclohex-1-yl, 4, 4 -dichlorocyclohex-1-yl or 4, 4 -difluorocyclo-hex -l-yl;
  • 6-link rings such as:
  • 1,2,3, 6-tetrahydropyridazin-4-yl 4H-5, 6-dihydro-l, 3-oxazin-2-yl, 4H-5, 6-dihydro-l, 3-oxazin-4- yl, 4H-5,6-dihydro-1, 3-oxazin-5-yl, 4H-5, 6-dihydro-l, 3-oxazin-6-yl, 4H-5, 6-dihydro-l, 3-thiazin-2-yl, 4H-5, 6-dihydro-l, 3-thiazin-4-yl, 4H-5, 6-dihydro-l, 3-thiazin-5-yl, 4H-5, 6-dihydro-1,3-thiazin-6-yl, 3,4,5-6-tetrahydropyrimidin-2-yl, 3,4,5,6-tetrahydropyrimidin-4-yl, 3,4,5,6- Tetrahydropyrimidin-5-yl, 3, 4, 5, 6-tetrahydropyrimi
  • a bicyclic ring system can be formed with a fused-on phenyl ring or with a C 3 -C 6 carbocycle or with a further 5- to 6-membered heterocycle.
  • N-linked heterocyclyl a saturated, partially saturated or unsaturated 5- or 6-membered N-linked heterocyclic ring, the at least one nitrogen and optionally one to three identical or different heteroatoms, selected from the following group: oxygen, sulfur or contains nitrogen, for example
  • N-linked 5-membered rings such as:
  • N-linked 6-membered rings such as:
  • Piperidin-1-yl 1, 2, 3, 4-tetrahydropyridin-l-yl, 1,2,5,6-tetrahydropyridin-1-yl, 1, 4-dihydropyridin-l-yl, 1,2- Dihydropyridin-1-yl, hexahydropyrimidin-1-yl, hexahydropyrazin-1-yl, hexahydropyridazin-1-yl, tetrahydro-1, 3-oxazin-3-yl, tetrahydro-1, 3-thiazin-3- yl, tetrahydro-1, 4-thiazin-4-yl, tetrahydro-1, 4-oxazin-4-yl, tetrahydro-1, 2-oxazin-2-yl, 2H-5,6-dihydro 1, 2-oxazin-2-yl, 2H-5, 6-dihydro-l, 2-thiazin-2-yl, 2H-3, 6-dihydr
  • Phthalimide tetrahydrophthalimide, succinimide, maleimide or glutarimide, and also 4-oxo-1,4-dihydropyridin-1-yl;
  • Suitable heterocyclyl radicals are in particular 5-membered aromatic heterocycles such as 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, pyrrol-2-yl, pyrrol-3-yl, pyrazol-3- yl, pyrazol-4-yl, isoxazol-3-yl, isoxazol-4 -yl, isoxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, imidazole- 2-yl, imidazol-4-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, thiazol-2-yl, Thiazol-4-yl, thiazol-5-yl, 1, 2, 4 -triazol-3 -yl or tetrazol-5-yl;
  • 5-membered partially unsaturated heterocycles such as e.g. 4,5-dihydro-lH-pyrazol-3-yl, 4,5-dihydro-lH-pyrazol-4-yl, 4,5-dihydro-lH-pyrazol-5-yl, 4,5-dihydro- isoxazol -3 -yl, 4, 5-dihydroisoxazol-4-yl, 4, 5-dihydroisoxazol-5-yl, 4, 5 -dihydrooxazol -2 -yl, 4, 5-dihydrooxazol-2-yl, 4, 5-dihydrothiazol-2-yl or 4,5-dihydroimidazole -2 -yl;
  • 5-membered saturated heterocycles such as e.g. Tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydrothien-2-yl, tetrahydro-thien-3-yl, tetrahydropyrrol-2-yl, tetrahydropyrrol-3-yl, 1,3-dioxolan-2-yl, 1,3-dioxolan-4-yl, 1,3-oxathiolan-2-yl, 1,3-oxathiolan-4-yl, 1,3-oxathiolan-5-yl, 1,3-dithiolan-2-yl or 1,3-dithiolan-4-yl;
  • 6-membered aromatic heterocycles such as e.g. Pyridin-2-yl, pyridine-3-yl, pyridin-4 -yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidine-5-yl, pyrazin-2-yl, 1, 3, 5-triazin-2-yl, 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl or 1,2,4-triazin-6-yl;
  • 6-membered partially unsaturated heterocycles such as e.g.
  • 6-membered saturated heterocycles such as e.g. Tetrahydropyran-2-yl, tetrahydropyran-3 -yl, tetrahydropyran-4 -yl, piperidine-2-yl, piperidin-3 -yl, piperidin-4 -yl, tetrahydrothiopyran-2-yl, tetrahydrothiopyran 3 -yl, tetrahydrothiopyran-4 -yl, 1, 3-dioxan-2-yl, 1, 3 -dioxan-4 -yl, 1, 3 -dioxan-5-yl, 1,3-diethyl-2- yl, 1, 3 -dithian-4 -yl, 1, 3 -dithian-5 -yl, 1,3-oxathian-2-yl, 1, 3 -Oxathian-4 -yl, 1, 3 -Oxathian- 5-yl, tetrahydro-1,
  • the variables preferably have the following meaning, individually or in combination:
  • R ⁇ R 2 is hydrogen, -CC 6 alkyl, hydroxy, -C 6 alkoxy, C 6 -C 6 -alkylthio, di - (-C 6 - alkyl) amino, the alkyl radicals of the latter five substituents may be partially or fully halogenated and / or may carry one to three of the following groups: nitro, cyano, C 4 alkoxy, C 1 -C 4 alkylsulfonyl or C 1 -C 4 alkoxycarbonyl; in particular hydrogen, C 1 -C 4 alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1 -methylbutyl or 2-methylbutyl, hydroxy, C ⁇ -C 4 alkoxy such as methoxy, ethoxy, propoxy, 1-methylethoxy, Butoxy or 2-methyl-butoxy, C 1 -C 4 -alkylthio such as methylthio, ethylthio
  • R 1 and R 2 together form a -0- (CH 2 ) m -0-, -O- (CH 2 ) m -S-, -S- (CH 2 ) m -S-, -NR5- (CH 2 ) m -NR5-, -0- (CH 2 ) m -NR5-,
  • -S- (CH 2 ) m -NR 5 - or - (CH 2 ) p chain which can carry one to three radicals from the following group: halogen, cyano, C 1 -C alkyl or C 1 -C 4 -Alkoxycarbonyl; in particular R 1 and R 2 together form a -0-CH 2 ) m -0, -O- (CH 2 ) m -S-, -S- (CH 2 ) m -S or - (CH 2 ) p -
  • R 3 is hydrogen, nitro, cyano, halogen, Ci-C ß- alkyl,
  • Trifluoromethyl such as methoxy or ethoxy, C ⁇ -C 4 haloalkoxy, such as difluoromethoxy, trifluoro- methoxy, or chlorodif luormethoxy, -C-C 4 -alkylthio such as methylthio or ethylthio, C 1 -C -alkylsulfonyl such as methylsulfonyl or ethylsulfonyl, C ⁇ -C 4 -haloalkylsulfonyl such as difluoromethylsulfonyl, trifluoromethylsulfonyl (0) CH 3 ),
  • R 4 halogen, such as chlorine or bromine, or C 1 -C 4 alkyl such as methyl or ethyl;
  • R 5 is hydrogen or -CC alkyl, such as methyl or ethyl
  • Q is a radical of the formula Q 1 , Q 2 , Q 3 or Q 4
  • R ⁇ R ⁇ R 11 is hydrogen, halogen, cyano, -CC 6 alkyl
  • Ci-C ß -haloalkyl di- (-C-C 6 - alkoxy) methyl
  • C ⁇ -C 6 haloalkylthio Ci-C ⁇ alkylsulfonyl, C ⁇ -C 6 haloalkylsulfonyl, Ci-C ß alkylcarbonyl, Ci-C ö -haloalkylcarbonyl, C ⁇ -C 6 -alkoxycarbonyl or C ⁇ haloalkoxycarbonyl;
  • R 8 , R 10 , R 12 are hydrogen or Ci -C 6 alkyl; in particular hydrogen or -CC 4 alkyl, such as methyl or ethyl;
  • R 7 and R 8 or R 9 and R 10 or R 11 and R 12 together form a -0- (CH 2 ) u -0-, -O- (CH 2 ) U -S-, -S- (CH 2 ) U -S-, -0- (CH 2 ) v - or -S- (CH 2 ) V chain, which can be substituted by one to three radicals from the following group: halogen, cyano, C 1 -C 4 - Alkyl, C 1 -C 4 haloalkyl or
  • Ci-C ⁇ -alkyl C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, Ci-C ⁇ -alkylcarbonyl, C 2 -C 6 ⁇ alkenylcarbonyl, C 3 -C 6 -cycloalkylcarbonyl, Ci-C ⁇ -alkylamino-carbonyl, Ci-Cg-alkylcarbonyl-Ci-C ⁇ -alkyl or Ci-C ß -alkoxyimino-Ci-Cg-alkyl, the said
  • Alkyl and cycloalkyl radicals can be partially or completely halogenated and / or can carry one to three of the following groups: cyano, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkyl carbonyl, C 1 -C 4 ⁇ Alkoxycarbonyl, hydroxycarbonyl,
  • Phenyl, heterocyclyl, phenyl-Ci-C ⁇ - alkyl, heterocyclyl-Ci-C ß- alkyl, phenylcarbonyl or heterocyclylcarbonyl, the phenyl and heterocyclyl radical being the 6 latter substituents can be partially or completely halogenated and / or can carry one to three of the following radicals:
  • C 3 -C 6 cycloalkyl hydroxy, Ci-C ß- alkoxy, di-Ci-C ⁇ -alkylamino, or di- (C ⁇ -Cg-haloalkyl) amino, where the said alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and / or may carry one to three of the following groups: cyano, C 4 -alkoxy, C 4 alkylthio, C ⁇ -C4 ⁇ alkyl carbonyl or C ⁇ -C 4 -alkoxycarbonyl ;
  • Phenyl, heterocyclyl, phenoxy or heterocyclyloxy where the phenyl and heterocyclyl radicals of the latter substituents can be partially or completely halogenated and / or can carry one to three of the following radicals:
  • R 17 C ⁇ -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 cycloalkyl, C ⁇ -C 6 alkoxy or C 3 -C 6 alkenyloxy, wherein the said alkyl, cycloalkyl and alkoxy radicals can be partially or completely halogenated and / or can carry one to three radicals from the following group: cyano, C 1 -C 4 alkoxy or C 1 -C 4 alkylthio;
  • R 20 is a radical as mentioned under R 6 ;
  • R 21 is hydrogen, -CC 6 alkyl or Ci-C ⁇ haloalkyl; in particular hydrogen or -CC 4 alkyl such as methyl, ethyl, propyl, 1-methyl-eth-1-yl, or 1, 1-dimethyl-eth-l-yl;
  • R 22 is hydrogen or Ci -C 6 alkyl; in particular hydrogen or -CC 4 alkyl, such as methyl or ethyl;
  • R 23 C 1 -C 6 alkyl, Ci-C ⁇ haloalkyl, C 3 -C 6 cycloalkyl or C 3 -C 6 halocycloalkyl; in particular C ⁇ -C 6 alkyl or C 3 -C 6 cycloalkyl; extremely cyclopropyl;
  • R 24 is hydrogen
  • R 25 C ⁇ -C 6 -alkyl, C 6 haloalkyl, C 3 -C 6 -cycloalkyl or C 3 -C 6 halocycloalkyl; in particular Ci-C ⁇ -alkyl or C 3 -C 6 cycloalkyl;
  • the compounds la are particularly preferred, in particular the compounds la, where the variables have the following meaning, individually or in combination:
  • R 6 is hydroxy, mercapto, halogen, OR 13 , SR 13 , S0 2 R 14 - OS0 2 R 14 , NR 17 R 18 , ONR 18 R 19 or N-linked heterocyclyl, the heterocyclyl radical of the latter substituent being partially or completely C ⁇ -C nitro, cyano, C 4 alkyl, C 1 -C 4 haloalkyl, 4 alkoxy or C 1 -C 4 -haloalkoxy; may be halogenated and / or may carry one to three of the following radicals
  • R 7 , R 9 , R U are hydrogen, halogen, cyano, C 1 -C 6 -alkyl
  • -C-C 6 -haloalkyl di- (Ci-C ⁇ -alkoxy) -methyl, di- (C ⁇ -C 6 -alkylthio) -methyl, (C ⁇ -C 6 -alkoxy) (C ⁇ -C 6 -alkyl - thio) -methyl, hydroxy, Ci-C ß -alkoxy, Ci-C ⁇ -haloalkoxy, C ⁇ -C 6 -alkoxycarbonyloxy, Ci-C ⁇ -alkylthio or Ci-C ß -haloalkylthio;
  • R 8 , R 10 , R 12 are hydrogen or Ci -C 6 alkyl; in particular hydrogen or C 1 -C 4 alkyl, such as methyl or ethyl;
  • R 7 and R 11 together form a - (CH) V chain, which is optionally substituted by one to three -CC alkyl radicals;
  • R 13 C ⁇ -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C ⁇ -C 6 alkylcarbonyl, C 3 -C 6 -cycloalkyl- carbonyl, C 1 -C 6 -alkylaminocarbonyl, N, N-di- (Ci-C ⁇ - 1-alkyl) or C 1 -C 6 -alkylcarbonyl-C 6 -C 6 -alkyl, the alkyl or cycloalkyl radicals mentioned being partially or completely halogenated can and / or can carry one to three of the following groups:
  • Phenyl, heterocyclyl, phenoxy or heterocyclyloxy where the phenyl and heterocyclyl radicals of the latter substituents can be partially or completely halogenated and / or can carry one to three of the following radicals:
  • phenyl radicals of the above radicals can be partially or completely halogenated and / or can carry one to three of the following radicals:
  • R 7 , R 8 , R 9 , R 10 , R 1: 1 , R 12 are hydrogen or C 1 -C 4 alkyl, such as methyl or ethyl; especially hydrogen or methyl;
  • R 9 and R 10 together with the carbon to which they are attached form a carbonyl group
  • R 7 and R 11 together form a - (CH 2 ) - or - (CH 2 ) 2 chain;
  • Phenylthio where the phenyl radicals of the above substituted can be partially or completely halogenated and / or can carry one to three of the following radicals:
  • R 20 is a radical as mentioned under R 6 ;
  • R 21 are hydrogen, C 6 alkyl or Ci-C6 haloalkyl, • in particular C 1 -C 4 alkyl such as methyl, ethyl, 1-methyl - eth-l-yl, or 1, l, Dimethyleth- l-yl, or -CC haloalkyl such as 2-fluoroethyl or 2, 2, 2-trifluoroethyl;
  • R 22 are hydrogen, C 6 alkyl or C ⁇ -C 6 haloalkyl, in particular hydrogen, C 1 -C 4 alkyl, such as methyl or ethyl, or C 1 -C 4 haloalkyl such as trifluoromethyl; in particular hydrogen, methyl or trifluoromethyl;
  • R 20 is hydroxy, mercapto, halogen, OR 13 , SR 13 , S0 2 R 14 , OS0 2 R 14 , NR 17 R 18 , ONR 18 R 19 or N-linked heterocyclyl, the heterocyclyl radical of the latter substituent being partially or completely can be halogenated and / or can carry one to three of the following radicals: nitro, cyano, Cx ⁇ alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy; R 13 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl,
  • substituents can be partially or completely halogenated and / or can carry one to three of the following radicals: nitro, cyano, C 1 -C 4 alkyl, C ⁇ -C 4 haloalkyl, -C ⁇ C 4 alkoxy or C ⁇ -C 4 -haloalkoxy;
  • the said alkyl, cycloalkyl and alkoxy radicals can be partially or completely halogenated and / or can carry one to three of the following groups: cyano, -C-alkoxy, -C-C 4 -alkylthio, -C-C 4 -alkylcarbonyl or -C-C 4 -alkoxycarbonyl;
  • Phenyl, heterocyclyl, phenoxy or heterocyclyloxy where the phenyl and heterocyclyl radicals of the latter substituents can be partially or completely halogenated and / or can carry one to three of the following radicals:
  • R 17 C ⁇ -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 cycloalkyl, C ⁇ -C 6 alkoxy or C 3 -C 6 alkenyloxy, wherein the said alkyl, cycloalkyl and alkoxy radicals can be partially or completely halogenated and / or can carry one to three radicals from the following group: cyano, C 1 -C 4 alkoxy or C 1 -C 4 alkylthio; Phenyl, heterocyclyl, phenyl -C -C 6 alkyl or hetero - cyclyl -C -C 6 alkyl, where the phenyl or heterocyclyl radical of the four last-mentioned substituents can be partially or completely halogenated and / or one to three of the following Can carry leftovers:
  • R 21 -C 6 -alkyl such as methyl, ethyl, 1-methyl-eth-l-yl, or 1, 1-dimethyl-eth-1 -yl;
  • R 22 is hydrogen or -CC 6 alkyl such as methyl or ethyl; especially hydrogen or methyl;
  • R 24 is hydrogen
  • R 3 nitro, cyano, halogen, -CC 4 alkyl, C ! -C 4 haloalkyl, Ci-C ⁇ alkoxy, C 1 -C4 haloalkoxy, C 1 -C 4 alkylsulfonyl or C1-C4 haloalkylsulfonyl;
  • R 4 is halogen, such as chlorine or bromine, or C 3 -C 4 -alkyl, such as methyl or ethyl;
  • R 3 is nitro, cyano, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C ⁇ -C alkoxy, C 1 -C 4 haloalkoxy, C ⁇ -C 4 alkylthio, C ⁇ -C 4 - Haloalkylthio, C 1 -C 4 alkylsulfonyl or C 1 -C 4 haloalkylsulfonyl;
  • R 4 halogen, such as chlorine or bromine, or C 1 -C 4 alkyl such as methyl or ethyl;
  • R ⁇ R 2 is hydrogen, -CC 6 alkyl, hydroxy or -CC 6 alkoxy, where the alkyl radicals of the latter 3 substituents can be partially or completely halogenated and / or can carry one to three of the following groups: nitro, cyano , -CC 4 alkoxy, C 1 -C alkylsulfonyl or C 1 -C 4 alkoxycarbonyl; particularly preferably hydrogen, C 1 -C 4 alkyl or Ci -C 4 alkoxy;
  • R 7 , R 8 , R 9 , R 10 , R 1: L , R 12 are hydrogen or C 1 -C 4 alkyl
  • R ! R 2 C 3 -C 4 alkyl or Ci -C alkoxy
  • R 6 is hydroxy or phenylthio, where the phenyl radical can be partially or completely halogenated and / or can carry one to three of the following radicals: nitro, cyano, C ⁇ -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy;
  • R ⁇ R ⁇ R ⁇ R 10 ⁇ 11 ⁇ 12 is hydrogen or C 1 -C alkyl
  • R 7 and R 11 together form a - (CH 2 ) - or - (CH 2 ) 2 chain, in particular a - (CH) 2 chain.
  • R X , R 2 C 1 -C 4 alkyl or Ci -C alkoxy; in particular Ci-C 4 alkoxy;
  • R 20 hydroxy; R 21 Ci - C 4 alkyl;
  • R 22 is hydrogen or C x -C 4 alkyl; especially hydrogen.
  • the phosphorus-containing benzoyl derivatives of the formula I can be obtained in various ways, for example by the following processes:
  • Halogenating agent la with R halogen
  • Suitable halogenating agents are, for example, phosgene, diphosgene, triphosgene, thionyl chloride, oxalyl chloride, phosphorus oxychloride, phosphorus pentachloride, mesyl chloride, chloromethylene-N, N-dimethylammonium chloride, oxalyl bromide, phosphorus oxybromide etc.
  • the starting compounds are generally used in an equimolar ratio. However, it can also be advantageous to use one or the other component in excess.
  • solvents examples include chlorinated hydrocarbons such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons e.g. Toluene, xylene or chlorobenzene, polar aprotic solvents such as acetonitrile, dimethylformamide or dimethyl sulfoxide or mixtures thereof.
  • chlorinated hydrocarbons such as methylene chloride or 1,2-dichloroethane
  • aromatic hydrocarbons e.g. Toluene, xylene or chlorobenzene
  • polar aprotic solvents such as acetonitrile, dimethylformamide or dimethyl sulfoxide or mixtures thereof.
  • reaction temperature is in the range from 0 ° C. to the boiling point of the reaction mixture.
  • the product can be worked up in a manner known per se.
  • R 6 OR i3, OS0 2 R i4, OPR 15 R 16, OPOR l5 R 16 or OPSR l5 R l6
  • L 1 stands for a nucleophilically displaceable leaving group, such as halogen, e.g. B. chlorine or bromine, hetaryl, e.g. B. imidazolyl, carboxylate, e.g. B. acetate, or sulfonate, e.g. B. mesylate or triflate etc.
  • halogen e.g. B. chlorine or bromine
  • hetaryl e.g. B. imidazolyl
  • carboxylate e.g. B. acetate
  • sulfonate e.g. B. mesylate or triflate etc.
  • the compounds of formula Il ⁇ , Ilß, Il ⁇ , Il ⁇ or Il ⁇ can be used directly, such as. B. in the case of carboxylic acid halides or generated in situ, for. B. activated carboxylic acids (with carboxylic acid and dicyclohexylcarbodiimide etc.).
  • the starting compounds are generally used in an equimolar ratio. However, it can also be advantageous to use one or the other component in excess.
  • reaction it may also be advantageous to carry out the reaction in the presence of a base.
  • the reactants and the base are expediently used in equimolar amounts. An excess of the base e.g. 1.5 to 3 molar equivalents can be advantageous under certain circumstances.
  • Suitable bases are tertiary alkylamines, such as triethylamine, aromatic amines, such as pyridine, alkali metal carbonates, for example sodium carbonate or potassium carbonate, alkali metal hydrogen carbonates, such as sodium hydrogen carbonate and potassium hydrogen carbonate, alkali metal alcoholates such as sodium methoxide, sodium ethanolate, potassium tert. -butanolate or alkali metal hy- dide, eg sodium hydride. Triethylamine or pyridine are preferably used.
  • solvents examples include chlorinated hydrocarbons, such as methylene chloride or 1,2-dichloroethane, aromatic
  • Hydrocarbons e.g. Toluene, xylene or chlorobenzene, ethers such as diethyl ether, methyl tert. butyl ether, tetrahydrofuran or dioxane, polar aprotic solvents such as acetonitrile, dimethylformamide or dimethyl sulfoxide or esters such as ethyl acetate, or mixtures thereof.
  • ethers such as diethyl ether, methyl tert. butyl ether, tetrahydrofuran or dioxane
  • polar aprotic solvents such as acetonitrile, dimethylformamide or dimethyl sulfoxide or esters such as ethyl acetate, or mixtures thereof.
  • reaction temperature is in the range from 0 ° C. to the boiling point of the reaction mixture.
  • the product can be worked up in a manner known per se.
  • R 6 OR i3 , SR 13 , POR i5 R i6 , NR i7 R i8 , ONR i7 R 18 , N-bound heterocyclyl or ON-bound heterocyclyl
  • the starting compounds are generally used in an equimolar ratio. However, it can also be advantageous to use one or the other component in excess.
  • the reaction may also be advantageous to carry out the reaction in the presence of a base.
  • the reactants and the base are expediently used in equimolar amounts.
  • Suitable bases are tertiary alkyl amines such as triethylamine, aromatic amines such as pyridine, alkali metal carbonates, e.g. Sodium carbonate or potassium carbonate, alkali metal hydrogen carbonates, such as sodium hydrogen carbonate and potassium hydrogen carbonate, alkali metal alcoholates such as sodium methoxide, sodium ethanolate, potassium tert. butanolate or alkali metal hydrides, e.g. Sodium hydride. Sodium hydride or potassium tert are preferably used. -butanolate.
  • solvents examples include chlorinated hydrocarbons such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons e.g. Toluene, xylene or chlorobenzene, ethers such as diethyl ether, methyl tert. -butyl ether, tetrahydrofuran or dioxane, polar aprotic solvents, such as
  • reaction temperature is in the range from 0 ° C. to the boiling point of the reaction mixture.
  • the product can be worked up in a manner known per se.
  • Suitable oxidizing agents are m-chloroperbenzoic acid, peroxyacetic acid, trifluoroperoxyacetic acid, hydrogen peroxide, if appropriate in the presence of a catalyst such as tungstate.
  • the starting compounds are generally used in an equimolar ratio. However, it can also be advantageous to use one or the other component in excess.
  • solvents examples include chlorinated hydrocarbons such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons e.g. Toluene, xylene or chlorobenzene, ethers such as diethyl ether, methyl tert. butyl ether, tetrahydrofuran or dioxane, polar aprotic solvents such as acetonitrile or dimethylformamide or esters such as ethyl acetate, or mixtures thereof.
  • chlorinated hydrocarbons such as methylene chloride or 1,2-dichloroethane
  • aromatic hydrocarbons e.g. Toluene, xylene or chlorobenzene
  • ethers such as diethyl ether, methyl tert. butyl ether, tetrahydrofuran or dioxane
  • polar aprotic solvents such as acetonitrile or dimethylformamide or esters such as
  • reaction temperature is in the range from 0 ° C. to the boiling point of the reaction mixture.
  • the product can be worked up in a manner known per se.
  • L 2 stands for a nucleophilically displaceable leaving group, such as halogen, for example bromine or chlorine, hetaryl, for example imidazolyl or pyridyl, carboxylate, for example acetate or trifluoroacetate etc.
  • halogen for example bromine or chlorine
  • hetaryl for example imidazolyl or pyridyl
  • carboxylate for example acetate or trifluoroacetate etc.
  • the activated benzoic acid IV ⁇ can be used directly, as in the case of the benzoyl halides, or generated in situ, e.g. with dicyclohexylcarbodiimide, triphenylphosphine / azodicarboxylic acid ester, 2-pyridine disulfide / triphenylphosphine, carbonyldiimidazole etc.
  • auxiliary base It may be advantageous to carry out the acylation reaction in the presence of a base.
  • the reactants and the auxiliary base are expediently used in equimolar amounts.
  • a slight excess of the auxiliary base for example 1.2 to 1.5 molar equivalents, based on IV ⁇ or IVß may be advantageous under certain circumstances.
  • Tertiary alkyl amines, pyridine or alkali metal carbonates are suitable as auxiliary bases.
  • suitable solvents are chlorinated hydrocarbons, such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons, such as toluene, xylene or chlorobenzene, ethers, such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran or dioxane, polar aprotic solvents, such as acetonitrile, dimethylformamide or dimethyl sulfoxide or esters such as ethyl acetate or mixtures thereof.
  • chlorinated hydrocarbons such as methylene chloride or 1,2-dichloroethane
  • aromatic hydrocarbons such as toluene, xylene or chlorobenzene
  • ethers such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran or dioxane
  • polar aprotic solvents such as acetonitrile, dimethylformamide or
  • phosphorus-containing benzoyl halides are used as the activated carboxylic acid component, it may be expedient to cool the reaction mixture to 0-10 ° C. when this reactant is added. The mixture is then stirred at 20-100 ° C., preferably at 25-50 ° C., until the reaction is complete. The processing takes place in the usual way, e.g. the reaction mixture is poured onto water and the product of value is extracted. Methylene chloride, diethyl ether and ethyl acetate are particularly suitable as solvents for this. After drying the organic phase and removing the solvent, the crude ester can be used for rearrangement without further purification.
  • the rearrangement of the esters VI to the compounds of the formula Ia is advantageously carried out at from 20 to 100 ° C. in a solvent and in the presence of a base and, if appropriate, using a cyano compound as a catalyst.
  • solvent e.g. Acetonitrile, methylene chloride, 1, 2-dichloroethane, dioxane, ethyl acetate, toluene or mixtures thereof can be used.
  • Preferred solvents are acetonitrile and dioxane.
  • Suitable bases are tertiary amines such as triethylamine, aromatic amines such as pyridine or alkali carbonates such as sodium carbonate or potassium carbonate, which are preferably used in an equimolar amount or up to a fourfold excess, based on the ester.
  • Triethylamine or alkali carbonate are preferably used, preferably in a double equimolar ratio with respect to the ester.
  • Inorganic cyanides such as sodium cyanide or potassium cyanide and organic cyano compounds such as acetone cyanohydrin or trimethylsilyl cyanide are suitable as cyano compounds. They are used in an amount of 1 to 50 mole percent, based on the ester. Acetone cyanohydrin or trimethylsilyl cyanide, for example in a Amount of 5 to 15, preferably 10 mole percent, based on the ester, used.
  • the reaction mixture is e.g. acidified with dilute mineral acid such as 5% hydrochloric acid or sulfuric acid, with an organic solvent, e.g. Extracted methylene chloride or ethyl acetate.
  • the organic extract can be mixed with 5-10% alkali carbonate solution, e.g. Sodium carbonate or potassium carbonate solution can be extracted.
  • the aqueous phase is acidified and the precipitate formed is suction filtered and / or extracted with methylene chloride or ethyl acetate, dried and concentrated.
  • M stands for a metal, in particular for an alkali metal such as lithium or sodium, an alkaline earth metal such as magnesium or a transition metal such as palladium, nickel etc. and L 3 for a nucleophilically displaceable leaving group such as halogen, such as chlorine or bromine, alkyl sulfonate such as Mesylate, haloalkyl sulfonate such as triflate or cyanide.
  • halogen such as chlorine or bromine
  • alkyl sulfonate such as Mesylate
  • haloalkyl sulfonate such as triflate or cyanide.
  • the reaction is usually carried out at temperatures from -100 ° C. to the reflux temperature of the reaction mixture.
  • Inert aprotic solvents such as ethers, for example diethyl ether, tetrahydrofuran, are suitable as solvents.
  • the compounds of the formula IV ⁇ are generally used in excess, but it may also be advantageous to use them in equimolar amounts or in a deficit.
  • the processing takes place towards the product.
  • the metalated pyrazole derivatives of the formula VII can be formed in a manner known per se by reacting pyrazoles halogenated in the 4-position with metals such as lithium, sodium, magnesium etc. or with organometallic compounds such as butyllithium.
  • ester IX in situ by reacting a pyrazole of the formula VIII, or an alkali salt thereof, with a phosphorus-containing benzene derivative of the formula X in the presence of carbon monoxide, a catalyst and a base.
  • L 4 stands for a leaving group such as halogen, for example chlorine, bromine or iodine, or sulfonate such as mesylate or triflate; bromine or triflate are preferred.
  • halogen for example chlorine, bromine or iodine, or sulfonate such as mesylate or triflate; bromine or triflate are preferred.
  • the ester IX may react directly to the phosphorus-containing benzoyl derivative of the formula Ib.
  • Suitable catalysts are palladium ligand complexes in which the palladium is in oxidation state 0, metallic palladium, which has optionally been applied to a support, and preferably palladium (II) salts.
  • the reaction with palladium (II) salts and metallic palladium is preferably carried out in the presence of complex ligands.
  • a palladium (0) ligand complex for example, tetrakis (triphenylphosphine) palladium can be used.
  • Metallic palladium is preferably coated on an inert support such as activated carbon, silicon dioxide, aluminum oxide, barium sulfate or calcium carbonate.
  • the reaction is preferably carried out in the presence of complex ligands such as triphenylphosphine.
  • Suitable palladium (II) salts are, for example, palladium acetate and palladium chloride. It is preferred to work in the presence of complex ligands such as triphenylphosphine.
  • complex ligands such as triphenylphosphine.
  • Suitable complex ligands for the palladium ligand complexes, or in the presence of which the reaction with metallic palladium or palladium (II) salts is preferably carried out, are tertiary phosphines, the structure of which is given by the following formula:
  • R a to R9 are C ⁇ -C 6 alkyl, aryl-C ⁇ ⁇ C 2 alkyl or preferably aryl.
  • Aryl stands for example for naphthyl and optionally substituted phenyl such as 2-tolyl and in particular for unsubstituted phenyl.
  • the complex palladium salts can be prepared in a manner known per se from commercially available palladium salts such as palladium chloride or palladium acetate and the corresponding phosphanes such as e.g. Triphenylphosphan or 1, 2-bis (diphenylphosphano) ethane take place. Most of the complexed palladium salts are also commercially available.
  • Preferred palladium salts are [(R) (+) 2,2'-bis (diphenylphosphane) -1, l'-binaphthyl] palladium (II) chloride, bis (triphenylphosphine) palladium (II) acetate and in particular bis (triphenyl - phosphine) palladium (II) chloride.
  • the palladium catalyst is generally used in a concentration of 0.05 to 5 mol%, preferably 1-3 mol%.
  • Suitable bases are tertiary amines such as, for example, N-methylpiperidine, ethyldiisopropylamine, 1,8-bisdimethylaminonaphthalene or, in particular, triethylamine.
  • Alkali carbonate such as sodium carbonate or potassium carbonate, are also suitable. Mixtures of potassium carbonate and triethylamine are also suitable.
  • Nitriles such as benzonitrile and acetonitrile, amides such as dimethylformamide, dimethylacetamide, tetra-C 1 -C 8 -alkylureas or N-methylpyrrolidone and preferred wise ethers such as tetrahydrofuran, methyl tert. serve butyl ether.
  • ethers such as 1,4-dioxane and dimethoxyethane are preferred as solvents.
  • L 5 stands for an O-Ci-C ⁇ -alkyl or N (Ci-C ö -alkyl) 2 group.
  • the 1,3-dicarbonyl compound of the formula XI is reacted with hydroxylamine which is generated in situ, for example from a salt of hydroxylamine with a base or an acid acceptor such as triethylamine or sodium acetate.
  • the starting compound of the formula XI is obtained by reacting the known ⁇ -keto esters of the formula XII with an activated phosphorus-containing benzoic acid IV ⁇ .
  • the acylation product XIII is then converted, for example using p-toluenesulfonic acid as catalyst, into the 1,3-diketone XIV in an inert solvent such as toluene. This is then reacted with an orthoester or dimethylformamide dialkyl acetal to give the 1,3-dicarbonyl compound of the formula XI.
  • the ⁇ , ⁇ -unsaturated benzoyl derivative XV is obtained by ethinating the activated phosphorus-containing benzoic acid of the formula IV ⁇ .
  • Z stands for a metal such as lithium, an organotin residue such as Sn (C 4 H 9 ) 3 or a zinc residue such as ZnCl or ZnBr.
  • halogenating reagents such as thionyl chloride, thionyl bromide, phosgene, diphosgene, triphosgene, oxalyl chloride and oxalyl bromide.
  • the phosphorus-containing benzoic acids of the formula IVß are prepared in a known manner by acidic or basic hydrolysis from the corresponding phosphorus-containing benzoic acid esters iv ⁇ (cf. j. March, "Advanced Organic Chemistry", 4th edition, Wiley, New York, pp. 378 ff. )
  • T is C I -C ⁇ alkoxy
  • the phosphorus-containing benzoic acid esters IV ⁇ are available in different ways:
  • electrophilic aromatic substitution reaction may result in isomer mixtures which can be separated or purified by distillation, crystallization or chromatographic methods.
  • the reducing agents include Metals such as iron or zinc, in the presence of hydrochloric acid and catalytically activated hydrogen, (see J. March, “Advanced Organic Chemistry", 4th edition, p. 1216 ff.)
  • the latter can be converted into the corresponding N-alkyl derivatives by alkylation in the presence of a base.
  • R ' -C 6 alkyl
  • Ci - C 6 - haloalkyl It may be advantageous to carry out the reactions in the presence of metal catalysts such as copper (I) or palladium (II) (see, for example, Kikukawa et al., J. Org. Chem. 1983, 48, 1333)
  • Oxidizing agents such as bromine, peroxyacetic acid, m-chloroperbenzoic acid and hydrogen peroxide, optionally in the presence of a catalyst such as tungstate, can be obtained.
  • the sulfonic acid chloride is obtained by sulfochlorination of the corresponding diazonium salt.
  • suitable bases are in particular sodium carbonate, potassium carbonate, sodium hydride or potassium tert. -butanolate.
  • Suitable alkylation agents are preferably halogenated alkyl bromides or chlorides which may be halogenated (see, for example, H. Fener et al., "The Chemistry of the Ether Linkage", Wiley, New York, 1967, pp. 445-498.)
  • the phenols are accessible by "boiling" appropriate diazonium compounds.
  • a transition metal catalyst such as nickel or palladium
  • Phenyl or heterocyclyl Met Sn (-CC 4 -alkyl) 3 , B (OH) 2 , ZnBr, ZnCl Phosphorus-containing benzoic acid esters of the formula IV ⁇ with
  • R 3 optionally sub.
  • Heterocyclyl can also be obtained by building the heterocycle from suitable precursors.
  • aldoximes of the formula XIX can be used to produce 1, 2, 4 -oxadiazoline derivatives by condensation with aldehydes of the ketones (cf., for example, Arch. Phar. 1993, 326, 383-389).
  • the thioamides of the formula XX are suitable precursors for 2 -thiazolinyl derivatives (see, for example, Tetrahedron 1986, 42, 1449-1460) and for 2 -thiazolyl derivatives (see, for example, Houben-Weyl, "Methods of Organic Chemistry", 4 Edition, Vol. E5, pp. 1268 ff. (1985).
  • the carboxylic acids of the formula XXI are 2 -oxazolinyl-,
  • 1, 3-thiazol-5 (4H) thion-2-yl or 5-oxo-2-imidazolin-2 can be obtained from carboxylic acid halides of the formula XXII, where shark represents halogen, in particular from carboxylic acid chlorides -yl derivatives are produced (see, for example, Helv. Chim. Acta, 1986, 69, 374-388; Heterocycles 1989, 29, 1185-1189).
  • oximes of the formula XXIV into 4, 5-dihydroisoxazol-3-yl or isoxazol-3-yl derivatives can be carried out in a manner known per se via the intermediate stage of the hydroxamic acid chlorides or bromides. Nitrile oxides are generated from the latter in situ, which react with alkenes or alkynes to give the desired products (see e.g. Chem. Ber. 1973, 106, 3258-3274). 1,3-Dipolar cycloaddition with chlorosulfonyl isocyanate to the nitrile oxide formed in situ gives 1,2,4-oxadiazolin-5-one-3-yl derivatives (cf. e.g. Heterocycles 1988, 27, 683-685).
  • the aldehydes of the formula XXV can be converted via the intermediate stage of the semicarbazones into 2,4-dihydro-1,2,4-triazol-3-one-5-yl derivatives (see, for example, J. Heterocyclic Chem. 1986, 23, 881-883).
  • 2 -Imidazolinyl derivatives can be prepared from benzonitriles of the formula XXVI by known methods (cf., for example, J. Org. Chem. 1987, 52, 1017-1021.
  • 1, 2, 4-triazol-3-yl derivatives can also be prepared from the benzonitriles of the formula XXVI (cf. e.g. J. Chem. Soc. 1954, 3461-3464).
  • the aldehydes XXV can be prepared in a manner known per se by means of the Wittig reaction with phosphonium salts (Ph) 3 P + CH 2 COR * ⁇ - (J. March, "Advanced Organic Chemistry", 3rd edition, p 864 ff., Wiley-Interscience Publication, 1985) to convert ⁇ , ⁇ -unsaturated ketones XXVII. Reaction with hydroxylamine gives the corresponding oximes, which can be converted into the 5-isoxazolyl derivatives by means of oxidative cyclization (J. Am. Chem. Soc. 1972, 94, 9128) (the meaning of R * thus corresponds to the meaning of a radical by which heterocyclyl can be substituted).
  • aldehydes XXV with alkoxymethylphosphonium salts can be converted to the corresponding enol ethers in a manner known per se (J. March, "Advanced Organic Chemistry", 3rd edition, pp. 864 ff., Wiley-Interscience Publication, 1985). Cleavage of these enol ethers in analogy to methods known from the literature leads to the acetaldehyde derivatives XXVIII. These can be converted into the ⁇ -bromoacetaldehyde derivatives by bro ating in the ⁇ -position (Tetrahedron Lett. 1988, 29, 5893), which, by cyclization with amides, thioamides and amidines, give oxazoles, thiazoles and imidazoles. Furthermore, the acetaldehyde derivatives
  • XXVIII with dimethylformamidimethylacetal are converted into corresponding enamines, which can then be converted to isoxazoles or pyrazoles with hydroxylamines or hydrazines.
  • aldehydes XXV can be converted into hydroxyketone derivatives by means of an aldol reaction with ketones. Subsequent oxidation leads to 1,3-diketones which can be converted to isoxazoles, pyrazoles or pyrimidines using hydroxylamine, hydrazines or amidines.
  • aldehydes XXV can be converted into the corresponding diazo compounds XXIX by methods known from the literature (Houben-Weyl, "Methods of Organic Chemistry", 4th Edition, Volume E14b). 1,3-dipolar cycloaddition on alkenes or Alkynes and subsequent isomerization lead to pyrazolines or pyrazoles.
  • the aldehyde XXV can be used analogously to processes known from the literature, e.g. from the corresponding methyl compound XXX by bromination, for example with N-bromosuccinimide or 1, 3-dibromo-5, 5-dimethylhydantoin, and subsequent oxidation (cf. Synth. Commun. 1992, 22, 1967-1971).
  • the oximes of formula XXIV are advantageously obtained by reacting aldehydes of formula XXV with hydroxylamine in a manner known per se (cf. J. March, "Advanced Organic Chemistry", 3rd edition, pp. 805-806, Wiley, New York, 1985).
  • the conversion of the oxime XXIV into the nitrile XXVI can also be carried out according to methods known per se (cf. J. March, "Advanced Organic Chemistry", 3rd edition, pp. 931-932, Wiley, New York, 1985).
  • nitriles of the formula XXVI can be converted in a manner known per se with hydroxylamine into the corresponding aldoximes XIX, with hydrogen sulfide into the thioamides XX or can be saponified to give the carboxylic acids XXI.
  • the latter can also be obtained by oxidation from aldehydes XXV (cf. J. March, "Advanced Organic Chemistry", 3rd edition, p. 629 ff., Wiley, New York, 1985).
  • the acid halides XXII can be obtained analogously to the standard processes from the corresponding carboxylic acids of the formula XXI.
  • Halogenating agents include Phosgene, thionyl chloride and thionyl bromide into consideration.
  • Suitable oxidizing agents are e.g. Potassium permanganate (see, for example, Houben Weyl, "Methods of Organic Chemistry", vol. IV / la, 1981, and vol. VIII, 1952; EI Bengtsson, Acta Chem. Scand. 1953, 7, 774), chromium (VI) Compounds (see, for example, AW Singer et al., Org. Synth. Coll. Vol. III 1955, 740) or atmospheric oxygen in the presence of a catalyst such as, for example Cobalt or manganese (see e.g. A.S. Hay et al., Can. J. Chem. 1965, 43, 1306).
  • a catalyst such as, for example Cobalt or manganese
  • Suitable oxidizing agents are e.g. Hydrogen peroxide, peroxyacetic acid etc.
  • R 2 C ⁇ -C 6 alkoxy, Ci-C ⁇ alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl etc.
  • Suitable alkyl halides are preferably the corresponding bromides and iodides (cf., for example, BA Arbuzow, Pure Appl. Chem. 1964, 9, 307; GM Kosolapoff, Org. React. 1951, 6, 273).
  • the substituents R i and R 2 can be modified at a suitable stage of the reaction sequence.
  • Corresponding organolithium or organomagnesium compounds can be considered as organometallic reagents (cf., for example, Houben-Weyl, "Methods of Organic Chemistry", Vol. E. 2, pp. 38f., Wiley, New York).
  • R i, R 2 are hydrogen, C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C ⁇ -C 6 -alkoxy, C 3 -C ö alkenyloxy, C 3 -C 6 -Alkynyloxy, mercapto, -C-C 6 -alkylthio, C 3 -C 6 -alkenylthio, C 3 -C 6 -alkynylthio, amino, C ⁇ -C 6 -alkylamino, di- (-C ⁇ -C 6 - alkyDamino, ( .
  • Phenoxy which can be partially or completely halogenated and / or can carry one to three of the following groups:
  • R and R 2 together form a -0- (CH 2 ) m -0-, -0- (CH 2 ) m -S-, -S- (CH 2 ) m -S-, -NR 5 - (CH 2 ) m -NR 5 -, -0- (CH 2 ) m -NR 5 -, -S- (CH 2 ) m -NR 5 -, - (CH 2 ) n -0-, - (CH 2 ) n - S or - (CH 2 ) n -NR 5 chain, which can carry one to three radicals from the following group:
  • Ri and R 2 together form a - (CH 2 ) p chain, which can be interrupted by oxygen, sulfur or NR 5 and / or can carry one to three radicals from the following group:
  • R 3 cyano, halogen, -CC 6 -alkyl, -C-C 6 -haloalkyl, Ci-Ce-Al oxy-Ci-C ⁇ -alkyl, Ci -C 6 -haloalkoxy-Ci -C 6 - al - kyl, C ⁇ -C 6 -alkylthio-C ⁇ -C 6 -alkyl, C 6 -C -Alkylsulfi- nyl-C 6 alkyl, Ci-C6 alkylsulfonyl -C -C 6 alkyl, Ci-C ⁇ - alkylcarbonyl, Ci-C ⁇ -alkoxy, CI-C ⁇ -haloalkoxy, C ⁇ -C 6 -alkylthio, C ⁇ -C 6 - haloalkylthio, C ⁇ -C 6 -alkylsulfinyl, Ci-C ⁇ -haloalkylsul
  • R 5 is hydrogen, Ci-C ⁇ -alkyl, -C-C 6 haloalkyl or Ci-C ⁇ -alkoxy;
  • hydrolyzable residues are alkoxy, phenoxy, Al kylthio, phenylthio residues, which may be substituted; Halides, heteroaryl radicals which are bonded via nitrogen; Amino, imino residues, which can possibly be sub etc.
  • TC I -C ⁇ -alkoxy means.
  • Rl, R 2 is hydrogen, -CC 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, Ci-C ⁇ -alkoxy, C 3 -C 6 alkenyloxy, C 3 -C 6 alkynyloxy , mercapto, C ⁇ -C 6 alkylthio, C 3 -C ö -alkenylthio, C 3 -C 6 -Alki- nylthio, amino, C ⁇ -C 6 -alkylamino or di- (C ⁇ -C ⁇ - alkyl) amino, wherein the alkyl, alkenyl or alkynyl radicals mentioned can be partially or completely halogenated and / or can carry one to three of the following groups:
  • Phenoxy which can be partially or completely halogenated and / or can carry one to three of the following groups: nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl,
  • R i and R 2 together form a -0- (CH 2 ) m -0-, -0- (CH 2 ) m -S-, -S- (CH 2 ) m -S-, -NR 5 - (CH 2 ) m -NR 5 -, -0- (CH 2 ) m -NR 5 - or -S- (CH 2 ) m -NR 5 chain, which can carry one to three radicals from the following group: halogen, cyano , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkoxycarbonyl or phenyl which is unsubstituted or partially or fully halogenated and / or one to three of the following groups: nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, Ci -C 4
  • R 2 phenyl or heterocyclyl, where the two last-mentioned radicals to be partially or fully halogenated and / or may carry one to three of the following groups: nitro, cyano, C 4 alkyl, C 1 -C 4 haloalkyl, C ! -C - alkoxy, C 1 -C 4 haloalkoxy or C 1 -C 4 alkoxycarbonyl;
  • R 5 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl or C 1 -C 6 -alkoxy;
  • R X , R 2 are hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy or C 1 -C 6 -alkylthio, where the alkyl radicals mentioned can be partially or completely halogenated and / or can carry one to three of the following groups: Nitro, cyano, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, di (C 1 -C 4 alkyl) amino, C 1 -C 4 alkylcarbonyl or Ci - C 4 alkoxycarbonyl, -
  • R 3 is cyano, halogen, C ⁇ -C 6 -alkyl, C 6 haloalkyl,
  • the O-acylated product (0.36 g) thus obtained was then mixed with potassium carbonate in 1,4-dioxane and heated under reflux for 4 hours.
  • the reaction mixture was poured into water and extracted with ethyl acetate.
  • the aqueous phase was washed once with diethyl ether, adjusted to pH 4 with hydrochloric acid and extracted with ethyl acetate.
  • the organic phase was dried and the solvent was removed.
  • tables 3 to 7 list further ones which were prepared or can be prepared in an analogous manner:
  • the compounds of formula I and their agriculturally useful salts are suitable both as isomer mixtures and in the form of the pure isomers - as herbicides.
  • the herbicidal compositions which contain compounds of the formula I control vegetation very well on non-cultivated areas, especially when high amounts are applied. In crops such as wheat, rice, corn, soybeans and cotton, they act against weeds and grass weeds without significantly damaging the crop plants. This effect occurs above all at low application rates.
  • the compounds of the formula I or herbicidal compositions comprising them can also be used in a further number of crop plants for eliminating undesired plants.
  • the following crops are considered, for example:
  • Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarle, Seeale Solanum tuberosum, sorghum bicolor (see vulgar), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.
  • the compounds of the formula I can also be used in crops which are tolerant to the action of herbicides by breeding, including genetic engineering methods.
  • the compounds of the formula I or the herbicidal compositions comprising them can be used, for example, in the form of directly sprayable aqueous solutions, powders, suspensions, including high-strength aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, Scattering agents or granules can be applied by spraying, atomizing, dusting, scattering or pouring.
  • the application forms depend on the purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • the herbicidal compositions comprise a herbicidally effective amount of at least one compound of the formula I or an agriculturally useful salt of I and auxiliaries customary for the formulation of crop protection agents.
  • Mineral oil fractions from medium to high boiling point such as kerosene and diesel oil, also coal tar oils as well as oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Paraffin, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes or their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, strongly polar solvents, e.g. Amines such as N-methylpyrrolidone and water.
  • Paraffin Paraffin, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes or their derivatives
  • alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol
  • ketones such as cyclo
  • Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water.
  • the phosphorus-containing benzoyl derivatives of the formula I as such or dissolved in an oil or solvent, can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers. However, it can also consist of active substance, wetting, adhesive,
  • Dispersants or emulsifiers and possibly solvents or oil existing concentrates are prepared which are suitable for dilution with water.
  • the surface-active substances are the alkali metal, alkaline earth metal and ammonium salts of aromatic sulfonic acids, for example lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa- , Hepta- and octadecanols as well as fatty alcohol glycol ether, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl, octyl or nonylphenyl glycolphenyl, alkylphen -
  • Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
  • Granules e.g. Coated, impregnated and homogeneous granules can be produced by binding the active ingredients to solid carriers.
  • Solid carriers are mineral soils such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, Ammonium nitrate, ureas and vegetable products such as corn flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
  • concentrations of the compounds of the formula I in the ready-to-use preparations can be varied within a wide range.
  • the formulations contain from about 0.001 to 98% by weight, preferably 0.01 to 95% by weight, of at least one active ingredient.
  • the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).
  • the application rates of the compound of the formula I are 0.001 to 3.0, preferably 0.01 to 1.0 kg / ha of active substance (as specified), depending on the control target, the season, the target plants and the growth stage.
  • the phosphorus-containing benzoyl derivatives of the formula I can be mixed with numerous representatives of other herbicidal or growth-regulating active compound groups and applied together.
  • Plastic flower pots with loamy sand with about 3.0% humus as substrate served as culture vessels.
  • the seeds of the test plants were sown separately according to species.
  • the active ingredients suspended or emulsified in water were applied directly after sowing using finely distributing nozzles.
  • the tubes were lightly sprinkled to promote germination and growth, and then covered with clear plastic hoods until the plants had grown. This cover causes the test plants to germinate evenly, provided that this has not been impaired by the active ingredients.
  • test plants For the purpose of post-emergence treatment, the test plants, depending on the growth habit, were first grown to a height of 3 to 15 cm and only then treated with the active ingredients suspended or emulsified in water. For this purpose, the test plants were either sown directly and grown in the same containers or they were first grown separately as seedlings and transplanted into the test containers a few days before the treatment.
  • the application rate for post-emergence treatment was 0.5 or 0.25 kg / ha a.S. (active substance).
  • the plants were kept in a species-specific manner at temperatures of 10 to 25 ° C and 20 to 35 ° C.
  • the trial period lasted 2 to 4 weeks. During this time, the plants were cared for and their response to each treatment was evaluated.
  • Evaluation was carried out on a scale from 0 to 100. 100 means no emergence of the plants or complete destruction of at least the aerial parts and 0 means no damage or normal growth.
  • the plants used in the greenhouse experiments are composed of the following types: At application rates of 0.5 or 0.25 kg / ha aS, compound 3.4 shows a very good effect against the undesired plants listed above.

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Abstract

The invention relates to phosphoric benzoyl derivatives of formula (I), in which the variables have the following meanings: P(=X)R<1>R<2>X represents an organic phosphorous group; R<3> represents hydrogen, nitro, cyano, halogen, optionally substituted alkyl, alkylcarbonyl, alkoxycarbonyl, optionally substituted alkoxy, optionally substituted alkylthio, optionally substituted alkylsulfinyl, optionally substituted alkylsulfonyl, optionally substituted aminosulfonyl, optionally substituted amino, P(=X)R<1>R<2>, optionally substituted phenyl or optionally substituted heterocyclyl; R<4> represents nitro, cyano, halogen, alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl; l is 0, 1 or 2; Q represents optionally substituted 1-hydroxy-3-oxo-cylcohex-1-ene-2-yl, optionally substituted 5-hydroxy-pyrazole-4-yl, optionally substituted isoxazole-4-yl or optionally substituted 2-cyano-1-oxo-eth-2-yl. The invention also relates to their agriculturally useful salts, to methods and intermediates for producing said phosphoric benzoyl derivatives, to agents containing them, to the use of said derivatives or of the agents containing them for controlling undesirable plants.

Description

PHOSPHORHALTIGE BENZOYL-DERIVATE UND PHOSPHOROUS BENZOYL DERIVATIVES AND
IHRE VERWENDUNG ALS HERBIZIDEYOUR USE AS HERBICIDES
Die vorliegende Erf indung betrif f t phosphorhaltige Benzoyl -Deri - vate der Formel IThe present invention relates to phosphorus-containing benzoyl derivatives of the formula I.
in der die Variablen folgende Bedeutung haben:in which the variables have the following meaning:
X Sauerstoff oder Schwefel;X oxygen or sulfur;
R!,R2 Wasserstoff, Cι-C6-Alkyl, C2 -C6-Alkenyl, C2-C6-Alkinyl, Hydroxy, Ci-Cδ-Alkoxy, C3-C6-Alkenyloxy, C3-C6-Alkinyl- oxy, Mercapto, Ci-Cβ-Alkylthio, C -C6-Alkenylthio, C3-C6-Alkinylthio, Amino, Ci-Cδ-Alkyla ino, Di- (Cι-C6-alkyl) amino, (Ci-Cε -Alkoxy) (Ci-Cδ-al- kyl) -amino, (C3 -Ce-Alkenyl) (Cι-C6 -alkyl) amino,R !, R 2 is hydrogen, -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, hydroxy, Ci-C δ -alkoxy, C 3 -C 6 -alkenyloxy, C 3 - C 6 -alkynyloxy, mercapto, Ci-Cβ-alkylthio, C -C 6 -alkenylthio, C 3 -C 6 -alkynylthio, amino, Ci-C δ -alkyla ino, di- (-C-C 6 -alkyl) amino, (Ci-Cε-alkoxy) (Ci-C δ -alkyl) -amino, (C 3 -Ce-alkenyl) (-C-C 6 -alkyl) amino,
(C3-C6-Alkinyl) (Cι-C6- alkyl) amino, Di (C3-C6-alke- nyDamino oder Di- (C3-C6-alkinyl) amino, wobei die genannten Alkyl-, Alkenyl- oder Alkinylreste partiell oder vollständig halogeniert sein können und/oder eine bis drei der folgenden Gruppen tragen können:(C 3 -C 6 alkynyl) (-C-C 6 alkyl) amino, di (C 3 -C 6 alkynylamino or di (C 3 -C 6 alkynyl) amino, where the alkyl, Alkenyl or alkynyl radicals can be partially or completely halogenated and / or can carry one to three of the following groups:
Nitro, Cyano, Cι-C4-Alkoxy, Cχ-C4-Alkylthio, C1-C4-AI- kylsulfinyl, C1-C4 -Alkylsulfonyl, Di(Cι-C4-al- kyl) -amino, Cι-C4-Alkylcarbonyl, Cι-C4-Alkoxycarbonyl , Phenyl oder Heterocyclyl, wobei die beiden letztgenannt ten Reste seinerseits partiell oder vollständig halogeniert sein können und/oder eine bis drei der folgenden Gruppen tragen können:Nitro, cyano, C 1 -C 4 -alkoxy, Cχ-C 4 -alkylthio, C 1 -C 4 -AI- alkylsulfinyl, C 1 -C 4 -alkylsulfonyl, di (Cι-C 4 -alkyl) -amino, Cι-C4-alkylcarbonyl, Cι-C 4 alkoxycarbonyl, phenyl or heterocyclyl, where the two last genann t th radicals may in turn be partially or fully halogenated and / or may carry one to three of the following groups:
Nitro, Cyano, Cι-C4-Alkyl, Cι-C4-Halogenalkyl, Cι-C4-Alkoxy, Cι-C4-Halogenalkoxy oder Cι-C4-Alkoxycar- bonyl ;Nitro, cyano, C 4 -alkyl, C 4 haloalkyl, Cι-C 4 -alkoxy, C 4 -haloalkoxy or Cι-C 4 -Alkoxycar- carbonyl;
Phenyl oder Phenoxy, das partiell oder vollständig halogeniert sein kann und/oder eine bis drei der folgenden Gruppen tragen kann: Nitro, Cyano, C1-C4 -Alkyl, Cι-C4-Halogenalkyl,Phenyl or phenoxy, which may be partially or fully halogenated and / or may carry one to three of the following groups: nitro, cyano, C 1 -C 4 -alkyl, C 4 haloalkyl,
Cι-C4-Alkoxy, C1-C -Halogenalkoxy oder Cι-C4-Alkoxycar- bonyl ; oderC 1 -C 4 alkoxy, C 1 -C haloalkoxy or C 1 -C 4 alkoxycarbonyl; or
R1 und R2 bilden gemeinsam eine -0- (CH )m-0- , -0- (CH )m-S- , -S- (CH2)m-S-, -NR5- (CH2)m-NR5-, -0- (CH2)m-NR5 - , -S- (CH2)m-NR5-, -(CH2)n-0-, -(CH2)n-S- oderR 1 and R 2 together form a -0- (CH) m -0-, -0- (CH) m -S-, -S- (CH 2 ) m -S-, -NR5- (CH 2 ) m -NR 5 -, -0- (CH 2 ) m -NR 5 -, -S- (CH 2 ) m -NR 5 -, - (CH 2 ) n -0-, - (CH 2 ) n -S- or
- (CH )n-NR5-Kette aus, die einen bis drei Reste aus folgender Gruppe tragen kann:- (CH) n -NR 5 chain, which can carry one to three residues from the following group:
Halogen, Cyano, C1-C4 -Alkyl, Cι-C4-Halogenalkyl,Halogen, cyano, C 1 -C 4 -alkyl, C 4 haloalkyl,
C1-C4 -Alkoxy, Cχ-C -Alkoxycarbonyl oder Phenyl, das un- substituiert ist oder partiell oder vollständig halogeniert ist und/oder eine bis drei der folgenden Gruppen tragen kann:C 1 -C 4 alkoxy, Cχ-C alkoxycarbonyl or phenyl which is unsubstituted or partially or fully halogenated and / or can carry one to three of the following groups:
Nitro, Cyano, Cι-C4-Alkyl, Cχ-C4-Halogenalkyl, C1-C4-Alkoxy, Cχ-C4-Halogenalkoxy oder Cι-C4-Alkoxycar- bonyl;Nitro, cyano, C 4 alkyl, Cχ-C 4 haloalkyl, C 1 -C 4 alkoxy, Cχ-C4-haloalkoxy or Cι-C 4 -Alkoxycar- carbonyl;
oderor
R1 und R2 bilden gemeinsam eine - (CH )P-Kette, die durch Sauer- stoff, Schwefel oder NR5 unterbrochen sein kann und/ oder einen bis drei Reste aus folgender Gruppe tragen kann:R 1 and R 2 together form a - (CH) P chain, which can be interrupted by oxygen, sulfur or NR 5 and / or can carry one to three radicals from the following group:
Halogen, Cyano, Cι-C4-Alkyl, Cι-C4-Halogenalkyl, C1-C4 -Alkoxy, Cι-C4-Alkoxycarbonyl oder Phenyl, das un- substituiert ist oder partiell oder vollständig halogeniert ist und/oder eine bis drei der folgenden Gruppen tragen kann:Halogen, cyano, C 4 -alkyl, C 4 haloalkyl, C 1 -C 4 -alkoxy, C 4 -alkoxycarbonyl or phenyl which is substituted is un- or partially or completely halogenated and / or can carry up to three of the following groups:
Nitro, Cyano, C1-C4 -Alkyl, Cι-C4-Halogenalkyl, Cι-C4-Alkoxy, Cι-C4-Halogenalkoxy oder Cι-C4-Alkoxycar- bonyl;Nitro, cyano, C 1 -C 4 -alkyl, C 4 haloalkyl, Cι-C 4 -alkoxy, C 4 -haloalkoxy or Cι-C 4 -Alkoxycar- carbonyl;
R3 Wasserstoff, Nitro, Cyano, Halogen, Cι-C6 -Alkyl,R 3 is hydrogen, nitro, cyano, halogen, -CC 6 alkyl,
Ci-Cδ-Halogenalkyl, Cι-C6-Alkoxy-Cι-C6-alkyl, Cι-C6-Ha- logenalkoxy-Cχ-C6 -alkyl, Ci -C6 -Alkylthio-Ci-Cε-alkyl, Cι-C6-Alkylsulfinyl-Cι-C6-alkyl, Ci-Cδ-Alkylsulfo- nyl-Ci-Cδ-alkyl, Ci-Cε-Alkylcarbonyl, Cι-C6-Alkoxycarbo- nyl, Ci-Cß-Alkoxy, Ci-Cg-Halogenalkoxy, Cι-C6-Alkylthio, Cι-C6-Halogenalkylthio, Cι-C6 -Alkylsulfinyl, Cι-C6-Halo- genalkylsulfinyl, Ci-Cε -Alkylsulfonyl, Ci-Cε-Halogenal- kylsulfonyl, Aminosulfonyl, Ci-Cß-Alkylaminosulfonyl,Ci-C δ -haloalkyl, -C-C 6 -alkoxy-Cι-C 6 -alkyl, Cι-C 6 -haloalkoxy-Cχ-C 6 -alkyl, Ci -C 6 -alkylthio-Ci-Cε-alkyl, C 1 -C 6 -alkylsulfinyl-C 1 -C 6 -alkyl, Ci-C δ -alkylsulfonyl-Ci-C δ -alkyl, C 1 -C 6 -alkylcarbonyl, Cι-C 6 -alkoxycarbonyl, Ci-C ß - Alkoxy, Ci-Cg-haloalkoxy, Cι-C 6 -alkylthio, Cι-C 6 -haloalkylthio, Cι-C 6 -alkylsulfinyl, Cι-C 6 -halogenated alkylsulfinyl, Ci-Cε-alkylsulfonyl, Ci-Cε-haloal- kylsulfonyl, aminosulfonyl, Ci-C ß -alkylaminosulfonyl,
Di- (Cι-C6-alkyl) aminosulfonyl, (Cι-C6-Alkylsulfo- nyl) amino, (Ci-Cß-Halogenalkylsulfonyl) amino, N- (Ci-Cδ-Alkyl) -N- (Cι-C6 -alkylsulfonyl) amino, N- (Cι-C6-Alkyl) -N- (Ci-Cß-halogenalkylsulfonyl) amino, -P(=X)R1R2, Phenyl oder Heterocyclyl, wobei die beiden letztgenannten Reste partiell oder vollständig halogeniert sein können und/oder einen bis drei der folgenden Gruppen tragen können:Di- (Cι-C6 alkyl) aminosulfonyl, (Cι-C 6 -Alkylsulfo- nyl) amino, (Ci-C ß haloalkylsulfonyl) amino, N- (Ci-C δ -alkyl) -N- (Cι- C 6 -alkylsulfonyl) amino, N- (-C-C 6 -alkyl) -N- (Ci-C ß -halogenalkylsulfonyl) amino, -P (= X) R 1 R 2 , phenyl or heterocyclyl, the two the latter radicals can be partially or completely halogenated and / or can carry one to three of the following groups:
Nitro, Cyano, C1-C4-Alkyl, Cι-C4-Halogenalkyl, Cι-C4-Alkoxy, Cι-C4-Halogenalkoxy oder Cχ-C4-Alkoxycar- bonyl ;Nitro, cyano, C 1 -C 4 -alkyl, C 4 haloalkyl, Cι-C 4 -alkoxy, C 4 -haloalkoxy or Cχ-C 4 -Alkoxycar- carbonyl;
R4 Nitro, Cyano, Halogen, Ci-Cδ-Alkyl, Cχ-C6-Alkoxy,R 4 nitro, cyano, halogen, Ci-C δ alkyl, Cχ-C 6 alkoxy,
Ci-Cδ-Alkylthio, Ci-Cβ -Alkylsulfinyl oder Ci-Cδ-Alkyl- sulfonyl;Ci-C δ- alkylthio, Ci-Cβ-alkylsulfinyl or Ci-C δ -alkylsulfonyl;
R5 Wasserstoff, Ci-Cß-Alkyl, Ci-Cε-Halogenalkyl oder Ci -C6-Alkoxy;R 5 is hydrogen, Ci-C ß- alkyl, Ci-Cε-haloalkyl or Ci -C 6 alkoxy;
1 0,1 oder 2 ;1 0.1 or 2;
m 2,3 oder 4 ;m 2, 3 or 4;
n 3,4 oder 5 ;n 3, 4 or 5;
p 4,5 oder 6 ;p 4,5 or 6;
Q ein Rest der Formel Q1, Q2, Q3 oder Q4 Q is a radical of the formula Q 1 , Q 2 , Q 3 or Q 4
Q1 Q2 Q3 Q"Q 1 Q 2 Q 3 Q "
R6 Hydroxy, Mercapto, Halogen, OR13, SR13 , SOR14, S02R14,R 6 hydroxy, mercapto, halogen, OR 13 , SR 13 , SOR 14 , S0 2 R 14 ,
OS02R14, POR15R16, OPR15R16, OPOR15R16, OPSR15R16, NRl7Rl8, ONR18R19, N-gebundenes Heterocyclyl oder 0- (N-gebundenes Heterocyclyl), wobei der Heterocyclyl -Rest der bei- den letztgenannten Substituenten partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann:OS0 2 R 14 , POR 15 R 16 , OPR 15 R 16 , OPOR 15 R 16 , OPSR 15 R 16 , NRl 7 Rl8, ONR 18 R 19 , N-linked heterocyclyl or 0- (N-linked heterocyclyl), where the Heterocyclyl radical of the latter two substituents can be partially or completely halogenated and / or can carry one to three of the following radicals:
Nitro, Cyano, Cχ-C4-Alkyl, Cι-C4-Halogenalkyl, C1-C4-AI- koxy oder Cχ-C4-Halogenalkoxy; R7,R9,R1]- Wasserstoff, Nitro, Halogen, Cyano, Cι-C6-Alkyl, Ci-Cε-Halogenalkyl, Di- (Ci-Cε- alkoxy) -methyl, Di- (Cι-C6-alkylthio) -methyl, (Cι-C6 -Alkoxy) (Cι-C6-alkyl- thio) -methyl, Hydroxy, Ci-Cδ-Alkoxy, Ci-Cß-Halogen- alkoxy, Ci-Cg-Alkoxycarbonyloxy, Ci-Cδ-Alkylthio,Nitro, cyano, Cχ-C 4 -alkyl, Cι-C 4 -haloalkyl, C 1 -C 4 -AI- koxy or Cχ-C 4 -haloalkoxy; R 7 , R 9 , R 1] - hydrogen, nitro, halogen, cyano, -C-C 6 alkyl, Ci-Cε-haloalkyl, di- (Ci-Cε-alkoxy) methyl, di- (Cι-C 6 -alkylthio) -methyl, (-C-C 6 -alkoxy) (-C-C 6 -alkyl-thio) -methyl, hydroxy, Ci-C δ -alkoxy, Ci-C ß -haloalkoxy, Ci-Cg-alkoxycarbonyloxy , Ci-C δ alkylthio,
Ci-Cδ-Halogenalkylthio, Cχ-C6-Alkylsulfinyl, Ci-Cδ-Halogenalkylsulfinyl , Cι-C6-Alkylsulfonyl , Ci-Cε-Halogenalkylsulfonyl , Ci-Cε-Alkylcarbonyl , Cι-C6-Halogenalkylcarbonyl, Cι-C6-Alkoxycarbonyl oder Ci-Cε-Halogenalkoxycarbonyl;Ci-C δ -haloalkylthio, Cχ-C 6 -alkylsulfinyl, Ci-C δ -haloalkylsulfinyl, Cι-C 6 -alkylsulfonyl, Ci-Cε-haloalkylsulfonyl, Ci-Cε-alkylcarbonyl, Cι-C 6 -haloalkylcarbonyl, Cι-C 6 -alkoxycarbonyl or Ci-Cε-haloalkoxycarbonyl;
R8,R10,R12 Wasserstoff, Cx-Cδ-Alkyl, Cι-C6-Alkoxy, Cι-C6 -Aikylthio oder Cι-C6 -Alkoxycarbonyl;R 8 , R 10 , R 12 are hydrogen, Cx-C δ- alkyl, -C-C 6 -alkoxy, Cι-C 6 -alkylthio or Cι-C 6 -alkoxycarbonyl;
oderor
R7 und R8 oder R9 und R10 oder R11 und R12 bilden gemeinsam eine -O- (CH2)u-0-, -0- (CH2)U-S-, -S- (CH2)U-S-, -0-(CH2)v- oder -S- (CH ) V-Kette, die durch einen bis drei Reste aus folgender Gruppe substituiert sein kann:R 7 and R 8 or R 9 and R 10 or R 11 and R 12 together form an -O- (CH 2 ) u -0-, -0- (CH 2 ) U -S-, -S- (CH 2 ) U -S-, -0- (CH 2 ) v - or -S- (CH) V chain, which can be substituted by one to three radicals from the following group:
Halogen, Cyano, C1-C4 -Alkyl, Cι-C4-Halogenalkyl oder Ci -C4 -Alkoxycarbonyl ;Halogen, cyano, C 1 -C 4 -alkyl, C 4 haloalkyl or Ci-C4 alkoxycarbonyl;
oderor
R7 und R8 oder R9 und R10 oder R11 und R12 bilden gemeinsam eine - (CH2)W-Kette, die durch Sauerstoff oder Schwefel unterbrochen sein kann und/oder durch einen bis vier Reste aus folgender Gruppe substituiert sein kann: Halogen, Cyano, C1-C4 -Alkyl, Cι-C4-Halogenalkyl oderR 7 and R 8 or R 9 and R 10 or R 11 and R 12 together form a - (CH 2 ) W chain which can be interrupted by oxygen or sulfur and / or be substituted by one to four radicals from the following group can: halogen, cyano, C 1 -C 4 alkyl, -C-C 4 haloalkyl or
Ci -C4 -Alkoxycarbonyl ;Ci -C 4 alkoxycarbonyl;
oderor
R7 und R8 oder R9 und R10 oder R11 und R12 bilden gemeinsam eine Methylidengruppe, die durch einen bis zwei Reste aus folgender Gruppe substituiert sein kann: Halogen, Hydroxy, Formyl , Cyano, Ci-Cδ-Alkyl, Cι-C6 _Halogenalkyl, Ci-Cδ-Alkoxy, Ci-Cg-Halogenalkoxy, Ci-Cβ-Alkylthio, Ci-Cδ-Halogenalkylthio, Ci-Cδ-Alkyl- sulfinyl, Ci-Cg-Halogenalkylsulfinyl, Ci-Cβ-Alkyl- sulfonyl oder Ci-Cß-Halogenalkylsulfonyl;R 7 and R 8 or R 9 and R 10 or R 11 and R 12 together form a methylidene group which can be substituted by one or two radicals from the following group: halogen, hydroxyl, formyl, cyano, Ci-C δ- alkyl, -C-C 6 _ haloalkyl, Ci-C δ- alkoxy, Ci-Cg-haloalkoxy, Ci-Cβ-alkylthio, Ci-C δ -haloalkylthio, Ci-C δ -alkylsulfinyl, Ci-Cg-haloalkylsulfinyl, Ci Cβ-alkyl-sulfonyl or Ci-C ß -haloalkylsulfonyl;
oder R7 und R8 oder R9 und R10 oder R11 und R12 bilden gemeinsam mit dem Kohlenstoff an den sie gebunden sind eine Carbonyl - gruppe aus;or R 7 and R 8 or R 9 and R 10 or R 11 and R 12 together with the carbon to which they are attached form a carbonyl group;
oderor
R7 und R9 oder R9 und R11 oder R7 und R11 bilden gemeinsam eine - (CH ) V-Kette, die durch einen bis drei Reste aus folgender Gruppe substituiert sein kann: Halogen, Cι-C6 -Alkyl, Cι-C6 -Alkoxy, Hydroxy oderR 7 and R 9 or R 9 and R 11 or R 7 and R 11 together form a - (CH) V chain, which can be substituted by one to three radicals from the following group: halogen, -CC 6 alkyl, Cι-C 6 alkoxy, hydroxy or
Ci -C6 -Alkoxycarbonyl ;Ci -C 6 alkoxycarbonyl;
R13 Ci-Cε-Alkyl, C3-C6-Alkenyl, C3-C6-Halogenalkenyl,R 13 Ci-Cε-alkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl,
C3-C6-Alkinyl, C3-C6-Halogenalkinyl , C3-C6-Cycloalkyl, Cι-C20-Alkylcarbonyl, C -C6-Alkenylcarbonyl ,C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl, C 3 -C 6 cycloalkyl, Cι-C 20 alkylcarbonyl, C -C 6 alkenylcarbonyl,
C2-C6-Alkinylcarbonyl , C3-C6-Cycloalkylcarbonyl , Ci -C6 -Alkylaminocarbonyl , Cι-C6-Alkylcarbonyl-Cι-C6-al - kyl oder Ci-Cg-Alkoxyimino-Ci-Cδ-alkyl, wobei die genannten Alkyl- und Cycloalkylreste partiell oder voll- ständig halogeniert sein können und/oder eine bis drei der folgenden Gruppen tragen können: Cyano, Cχ-C4-Alkoxy, Cι-C4-Alkylthio, Di- (Cι-C4-al - kyl) -amino, Cι-C4-Alkylcarbonyl, Cι-C4-Alkoxycarbonyl, Cι-C4-Alkoxy-Cι-C4-alkoxycarbonyl, Di- (Cι-C4-alkyl) -ami- no-Cι-C4-alkoxycarbonyl, Hydroxycarbonyl , Cχ-C -Alkyl- aminocarbonyl , Di- (Cι-C4-alkyl) -aminocarbonyl, Amino - carbonyl, Cι-C4-Alkylcarbonyloxy oder C3-C6-Cycloalkyl;C 2 -C 6 -alkynylcarbonyl, C 3 -C 6 -cycloalkylcarbonyl, Ci -C 6 -alkylaminocarbonyl, Cι-C 6 -alkylcarbonyl-Cι-C 6 -al - alkyl or Ci-Cg-alkoxyimino-Ci-C δ - alkyl, where the alkyl and cycloalkyl radicals mentioned can be partially or completely halogenated and / or can carry one to three of the following groups: cyano, Cχ-C 4 alkoxy, Cι-C 4 alkylthio, di- (Cι- C 4 -al - kyl) amino, -C-C 4 -alkylcarbonyl, Cι-C 4 -alkoxycarbonyl, Cι-C 4 -alkoxy-Cι-C 4 -alkoxycarbonyl, di- (-C-C 4 -alkyl) -ami - No -CC-C 4 -alkoxycarbonyl, hydroxycarbonyl, C C-C -alkyl-aminocarbonyl, di- (-C-C 4 -alkyl) -aminocarbonyl, amino - carbonyl, -C-C 4 -alkylcarbonyloxy or C 3 -C 6 - Cycloalkyl;
Phenyl, Heterocyclyl, Phenyl-Ci-Cβ-alkyl , Heterocy- dyl-Ci-Cß-alkyl, Phenylcarbonyl , Heterocyclylcarbonyl,Phenyl, heterocyclyl, phenyl-Ci-Cβ-alkyl, heterocydyl-Ci-C ß- alkyl, phenylcarbonyl, heterocyclylcarbonyl,
Phenylaminocarbonyl oder Heterocyclylaminocarbonyl, wobei der Phenyl- und der Heterocyclyl-Rest der 8 letztgenannten Substituenten partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann:Phenylaminocarbonyl or heterocyclylaminocarbonyl, where the phenyl and heterocyclyl radicals of the last 8 substituents can be partially or completely halogenated and / or can carry one to three of the following radicals:
Nitro, Cyano, Cι-C4-Alkyl, Cι-C4-Halogenalkyl, Cι-C4-Alkoxy oder Cχ-C4-Halogenalkoxy;Nitro, cyano, C 4 -alkyl, C 4 haloalkyl, Cι-C 4 alkoxy or Cχ-C 4 haloalkoxy;
R14,R15,R16 C1-C6-Alkyl, C3-C6-Alkenyl, C3-C6-Halogenalkenyl , C3-C6-Alkinyl, C3-C6-Halogenalkinyl, C3-C6-Cycloalkyl,R 14 , R 15 , R 16 C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl, C 3 -C 6 cycloalkyl,
Hydroxy, Ci-Cε-Alkoxy, Amino, Ci-Cδ-Alkylamino,Hydroxy, Ci-Cε-alkoxy, amino, Ci-C δ -alkylamino,
Ci-Cß-Halogenalkylamino, Di- (Ci-Cδ- alkyl) amino oder Di- (Ci-Cg-Halogenalkyl) amino, wobei die genannten Alkyl-, Cycloalkyl- und Alkoxyreste par- tiell oder vollständig halogeniert sein können und/oder eine bis drei der folgenden Gruppen tragen können: Cyano, Cι~C4-Alkoxy, Cι~C4-Alkylthio, Di- (C1-C4- alkyl) -amino, C!-C4-Alkylcarbonyl oder C;ι.-C4-Alkoxy- carbonyl ;Ci-C ß -haloalkylamino, di- (Ci-C δ -alkyl) amino or di- (Ci-Cg-haloalkyl) amino, where the alkyl, cycloalkyl and alkoxy radicals mentioned can be partially or completely halogenated and / or can wear one to three of the following groups: Cyano, -C ~ C 4 alkoxy, C ~ ~ C 4 alkylthio, di- (C 1 -C 4 alkyl) amino, C ! -C 4 alkylcarbonyl or C; ι.-C 4 alkoxycarbonyl;
Phenyl, Heterocyclyl, Phenoxy oder Heterocyclyloxy, wobei der Phenyl- und der Heterocyclyl-Rest der letztgenannten Substituenten partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann: Nitro, Cyano, Cι-C4-Alkyl, Cx^-Halogenalkyl,Phenyl, heterocyclyl, phenoxy or heterocyclyloxy, where the phenyl and heterocyclyl radicals of the latter substituents can be partially or completely halogenated and / or can carry one to three of the following radicals: nitro, cyano, C 1 -C 4 -alkyl, Cx ^ Haloalkyl,
Cι-C4~Alkoxy oder Cι-C4-Halogenalkoxy;-C-C 4 ~ alkoxy or -C-C 4 haloalkoxy;
R17 Ci-Cβ -Alkyl, C3-C6-Alkenyl, C3 -C6-Halogenalkenyl ,R 17 Ci-Cβ alkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl,
C3-C6-Alkinyl, C3 -Cg-Halogenalkinyl , C3-C6-Cycloalkyl, Hydroxy, Cι-C6 -Alkoxy, C -C6 -Alkenyloxy oderC 3 -C 6 alkynyl, C 3 -Cg haloalkynyl, C 3 -C 6 cycloalkyl, hydroxy, -C-C 6 alkoxy, C -C 6 alkenyloxy or
C3 -Cβ-Alkinyloxy, wobei die genannten Alkyl-, Cyclo- alkyl- und Alkoxyreste partiell oder vollständig halogeniert sein können und/oder einen bis drei Reste der folgenden Gruppe tragen können: Cyano, Cι-C4-Alkoxy, Cι-C4-Alkylthio oderC 3 -C 6 -alkynyloxy, where the alkyl, cycloalkyl and alkoxy radicals mentioned can be partially or completely halogenated and / or can carry one to three radicals from the following group: cyano, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio or
Di- (C1-C4 -alkyl) -amino;Di (C 1 -C 4 alkyl) amino;
Phenyl, Heterocyclyl, Phenyl -Cι-C6- lkyl oder Heterocyclyl -Cι-C6- alkyl, wobei der Phenyl- oder Heterocyclyl - Rest der vier letztgenannten Substituenten partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann: Nitro, Cyano, Cι-C4-Alkyl, Cι-C4-Halogenalkyl, C1-C4 -Alkoxy oder Cι-C4-Halogenalkoxy;Phenyl, heterocyclyl, phenyl -C 6 -alkyl or heterocyclyl -C 6 -alkyl, where the phenyl or heterocyclyl radical of the four last-mentioned substituents can be partially or completely halogenated and / or carry one to three of the following radicals can: nitro, cyano, C 4 -alkyl, C 4 haloalkyl, C 1 -C 4 alkoxy or Cι-C 4 haloalkoxy;
R18 , R19 Cι - C6 -Alkyl , C3 -C6 -Alkenyl , C3 - C6 -Alkinyl oderR 18 , R 19 Cι - C 6 alkyl, C 3 -C 6 alkenyl, C 3 - C 6 alkynyl or
Ci - C6 - Alkylcarbonyl ;Ci - C 6 alkylcarbonyl;
u 2 bis 4 ;u 2 to 4;
v 1 bis 5 ;v 1 to 5;
w 2 bis 5 ;w 2 to 5;
R20 ein Rest wie unter R6 genannt;R 20 is a radical as mentioned under R 6 ;
R21 Wasserstoff, Ci-Cß-Alkyl, Cι-C6-Halogenalkyl, Hydroxy, Ci-Cß -Alkoxy oder Ci-Cδ-Halogenalkoxy; R22 Wasserstoff, Halogen, Cι-C6 -Alkyl, Ci-Cβ-Halogenalkyl , Hydroxy, Ci-Cδ-Alkoxy, Cι-C6-Halogenalkoxy, Ci-Cß-Al- kylthio oder Ci-Cδ-Halogenalkylthio;R 21 is hydrogen, Ci-C ß- alkyl, -C-C 6 -haloalkyl, hydroxy, Ci-C ß -alkoxy or Ci-C δ -haloalkoxy; R 22 is hydrogen, halogen, -CC 6 -alkyl, Ci-Cβ-haloalkyl, hydroxy, Ci-C δ -alkoxy, -C-C 6 -haloalkoxy, Ci-C ß -alkylthio or Ci-C δ -haloalkylthio ;
R23 Wasserstoff, Cι-C6-Alkyl, Ci-Cö-Halogenalkyl, C3-C6-Cy- cloalkyl oder C3-C6-Halogencycloalkyl;R 23 are hydrogen, C 6 alkyl, Ci-C ö haloalkyl, C 3 -C 6 -Cy- cloalkyl or C 3 -C 6 halocycloalkyl;
R24 Wasserstoff, Cι-C6-Alkoxycarbonyl, Cι-C6-Halogenalk- oxycarbonyl , Hydroxycarbonyl oder Cyano;R 24 is hydrogen, -CC 6 alkoxycarbonyl, -C-C 6 haloalkoxycarbonyl, hydroxycarbonyl or cyano;
R25 Cι-C6-Alkyl, Ci-Cς-Halogenalkyl , C3-C6-Cycloalkyl oder C3 -Cß-Halogencycloalkyl ;R 25 -CC 6 alkyl, Ci-Cς haloalkyl, C 3 -C 6 cycloalkyl or C 3 -C ß halocycloalkyl;
sowie deren landwirtschaftlich brauchbaren Salze.and their agriculturally useful salts.
Außerdem betrifft die Erfindung Verfahren und Zwischenprodukte zur Herstellung von Verbindungen der Formel I, Mittel welche diese enthalten, sowie die Verwendung der Verbindungen der Formel I und diese enthaltende Mittel zur Schädlingsbekämpfung.In addition, the invention relates to processes and intermediates for the preparation of compounds of the formula I, compositions which contain them, and to the use of the compounds of the formula I and compositions for controlling pests.
Aus der Literatur, beispielsweise aus DE-A 22 60 705 und DE-A 21 66 729 sind herbizid wirksame Phosphorthionoamidate bekannt. Weiterhin beschreibt US 3,775,057 Pyridinylphosphonate.Herbicidally active phosphorothionoamidates are known from the literature, for example from DE-A 22 60 705 and DE-A 21 66 729. No. 3,775,057 describes pyridinylphosphonates.
Ebenso sind substituierte Benzoyl -isoxazole bzw. -pyrazole sowie substituierte 2 - Phenyl -cyclohexan-1, 3 -dione bzw. 1 -Phenyl -2 -cyanoalkan-1, 3-dione, beispielsweise aus EP-A 418 175, EP-A 609 797, Wo 96/26 192, WO 96/26 206, EP-A 203 428, US 4,780,127, EP-A 315 075 sowie EP-A 625 505, bekannt.Substituted benzoyl isoxazoles or pyrazoles and substituted 2-phenyl-cyclohexane-1,3-diones or 1-phenyl-2-cyanoalkane-1,3-diones are likewise, for example from EP-A 418 175, EP-A 609 797, Wo 96/26 192, WO 96/26 206, EP-A 203 428, US 4,780,127, EP-A 315 075 and EP-A 625 505.
Die herbiziden Eigenschaften der bisher bekannten Verbindungen sowie die Verträglichkeit gegenüber Kulturpflanzen können jedoch nur bedingt befriedigen. Es lag daher dieser Erfindung die Aufgabe zugrunde, neue, insbesondere herbizid wirksame Verbindungen mit verbesserten Eigenschaften zu finden.However, the herbicidal properties of the compounds known hitherto and the compatibility with crop plants can only satisfy to a limited extent. It was therefore the object of this invention to find new, in particular herbicidally active compounds with improved properties.
Demgemäß wurden die Phosphor-haltigen Benzoyl-Derivate der Formel I sowie deren herbizide Wirkung gefunden.Accordingly, the phosphorus-containing benzoyl derivatives of the formula I and their herbicidal activity have been found.
Ferner wurden herbizide Mittel gefunden, die die Verbindungen I enthalten und eine sehr gute herbizide Wirkung besitzen. Außerdem wurden Verfahren zur Herstellung dieser Mittel und Verfahren zur Bekämpfung von unerwünschtem Pflanzenwuchs mit den Verbindungen I gefunden. Die Verbindungen der Formel I können je nach Substitutionsmuster ein oder mehrere Chiralitätszentren enthalten und liegen dann als Enantiomeren oder Diastereomerengemische vor. Gegenstand der Erfindung sind sowohl die reinen Enantiomeren oder Diastereomeren als auch deren Gemische.Furthermore, herbicidal compositions have been found which contain the compounds I and have a very good herbicidal action. In addition, processes for the preparation of these compositions and processes for controlling unwanted vegetation using the compounds I have been found. Depending on the substitution pattern, the compounds of the formula I can contain one or more centers of chirality and are then present as enantiomers or mixtures of diastereomers. The invention relates both to the pure enantiomers or diastereomers and to their mixtures.
Die Verbindungen der Formel I können auch in Form ihrer landwirtschaftlich brauchbaren Salze vorliegen, wobei es auf die Art des Salzes in der Regel nicht ankommt. Im allgemeinen kommen die Salze derjenigen Kationen oder die Säureadditionssalze derjenigen Säuren in Betracht, deren Kationen, beziehungsweise Anionen, die herbizide Wirkung der Verbindungen I nicht negativ beeinträchtigen.The compounds of the formula I can also be present in the form of their agriculturally useful salts, the type of salt generally not being important. In general, the salts of those cations or the acid addition salts of those acids whose cations or anions do not adversely affect the herbicidal activity of the compounds I
Es kommen als Kationen insbesondere Ionen der Alkalimetalle, vorzugsweise Lithium, Natrium und Kalium, der Erdalkalimetalle, vorzugsweise Calcium und Magnesium, und der Übergangsmetalle, vorzugsweise Mangan, Kupfer, Zink und Eisen, sowie Ammonium, wobei hier gewünschtenfalls ein bis vier Wasserstoffatome durch Cι-C4-Alkyl, Hydroxy-Cχ-C4-alkyl, C1-C4 -Alkoxy-Cι-C4 -alkyl , Hydro- xy-Ci -C4 -alkoxy-C1-C4-alkyl, Phenyl oder Benzyl ersetzt sein können, vorzugsweise Ammonium, Dimethylammonium, Diisopropylammoni - um, Tetramethylammonium, Tetrabutylammonium, 2- (2 -Hydroxyeth-1- oxy) eth-1-ylammonium, Di (2 -hydroxyeth-1 -yl) ammonium, Trimethyl- benzylammonium, des weiteren Phosphoniumionen, Sulfoniumionen, vorzugsweise Tri (Cι-C4-alkyl) sulfonium und Sulfoxoniumionen, vorzugsweise Tri (Cχ-C4-alkyl) sulfoxonium, in Betracht.The cations used are, in particular, ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium and magnesium, and of the transition metals, preferably manganese, copper, zinc and iron, and ammonium, where if desired one to four hydrogen atoms by Cι- C 4 alkyl, hydroxy-Cχ-C 4 alkyl, C 1 -C 4 alkoxy -CC-C 4 alkyl, hydroxy-Ci -C 4 alkoxy-C 1 -C 4 alkyl, phenyl or Benzyl can be replaced, preferably ammonium, dimethylammonium, diisopropylammonium, tetramethylammonium, tetrabutylammonium, 2- (2-hydroxyeth-1-oxy) eth-1-ylammonium, di (2-hydroxyeth-1-yl) ammonium, trimethylbenzylammonium , further phosphonium ions, sulfonium ions, preferably tri (-C 4 alkyl) sulfonium and sulfoxonium ions, preferably tri (C TriC 4 alkyl) sulfoxonium, into consideration.
Anionen von brauchbaren Säureadditionsalzen sind in erster Linie Chlorid, Bromid, Fluorid, Hydrogensulfat, Sulfat, Dihydrogen- phosphat, Hydrogenphosphat, Nitrat, Hydrogencarbonat, Carbonat, Hexafluorosilikat, Hexafluorophosphat, Benzoat sowie die Anionen von Cι-C4-Alkansäuren, vorzugsweise Formiat, Acetat, Propionat und Butyra .Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of C 1 -C 4 -alkanoic acids, preferably formate, acylate , Propionate and butyra.
Die für die Substituenten R^—R25 oder als Reste an Phenyl- und Heterocyclyl-Resten genannten organischen Molekülteile stellen Sammelbegriffe für individuelle Aufzählungen der einzelnen Gruppenmitglieder dar. Sämtliche Kohlenwasserstoffketten, also alle Alkyl-, Halogenalkyl-, Alkoxy-, Halogenalkoxy-, Aikylthio-, Halogenalkylthio-, Alkylsulfinyl-, Halogenalkylsulfinyl-, Alkylsulfonyl-, Halogenalkylsulfonyl-, Alkylaminosulfonyl- , Dialkyl- aminosulfonyl - , Alkylamino- , Dialkylamino- , Halogenalkylamino- , Di (halogenalkyl) amino- , N-Alkoxy-N-alkylamino- , N-Alkylsulfonyl- amino-, N-Halogenalkylsulfonylamino- , N-Alkyl-N-alkylsulfonyla- mino-, N-Alkyl-N-halogenalkylsulfonylamino- , Alkylcarbonyl-, Halogenalkylcarbonyl-, Alkoxycarbonyl-, Halogenalkoxycarbonyl - , Alkyla inocarbonyl-, Dialkylaminocarbonyl-, Alkoxyalkyl-, Halo- genalkoxyalkyl - , Alkylthioalkyl- , Alkylsulfinylalkyl - , Alkylsul- fonylalkyl-, Dialkoxymethyl - , Dialkylthiomethyl- , (Alkoxy) (alkyl - thio) methyl - , Alkylcarbonylalkyl- , Alkoxyiminoalkyl - , Alkoxy- carbonyloxy, Phenylalkyl-, Heterocyclylalkyl-, Dialkylaminoalko- xycarbonyl-, Alkoxyalkoxycarbonyl-, Alkenylcarbonyl-, N-Alkenyl- N-alkylamino-, Dialkenylamino- , Alkinylcarbonyl-, N-Alkinyl-N-al- kylamino-, Dialkinylamino- , Alkenyl-, Alkinyl-, Halogenalkenyl-, Halogenalkinyl-, Alkenyloxy, Alkenylthio- , Alkinyloxy und Alki- nylthio-Teile können geradkettig oder verzweigt sein. Sofern nicht anders angegeben tragen halogenierte Substituenten vorzugsweise ein bis fünf gleiche oder verschiedene Halogenatome. Die Bedeutung Halogen steht jeweils für Fluor, Chlor, Brom oder lod.The organic parts of the molecule mentioned for the substituents R ^ —R 25 or as residues on phenyl and heterocyclyl residues are collective terms for individual lists of the individual group members. All hydrocarbon chains, that is to say all alkyl, haloalkyl, alkoxy, haloalkoxy and aikylthio -, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, alkylamino, dialkylamino, haloalkylamino, di (haloalkyl) amino, N-alkoxy-N-alkylamino, N-alkylsulfonylamino, N-haloalkylsulfonylamino, N-alkyl-N-alkylsulfonylamino, N-alkyl-N-haloalkylsulfonylamino, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, Alkyla inocarbonyl, dialkylaminocarbonyl, alkoxyalkyl, halogenoalkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, dialkoxymethyl, dialkylthiomethyl, (alkoxy) (alkylthio) methyl, alkylcarbonylalkyl, alkoxyiminoalkyl, alkoxy - Carbonyloxy, phenylalkyl, heterocyclylalkyl, dialkylaminoalkoxy, carbonyl, alkoxyalkoxycarbonyl, alkenylcarbonyl, N-alkenyl, N-alkylamino, dialkenylamino, alkynylcarbonyl, N-alkynyl-N-alkylamino, dialkinylamino, alkenylamino -, Alkynyl, haloalkenyl, haloalkynyl, alkenyloxy, alkenylthio, alkynyloxy and alkynylthio parts can be straight-chain or branched. Unless stated otherwise, halogenated substituents preferably carry one to five identical or different halogen atoms. Halogen is fluorine, chlorine, bromine or iodine.
Ferner bedeuten beispielsweise:Furthermore, for example:
Cι-C -Alkyl: z.B. Methyl, Ethyl, Propyl, 1-Methylethyl, Butyl, 1-Methylpropyl, 2-Methylpropyl oder 1, 1-Dimethylethyl;-C -C alkyl: e.g. Methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl or 1, 1-dimethylethyl;
- Ci-Cδ-Alkyl, sowie die Alkylteile von Cι-C6-Alkylcarbo- nyl-Cι-C6- lkyl, Cι-C6-Alkoxyimino-Cι-C6-alkyl, N-(C3-C6- Alkenyl) -N- (Cι-C6-alkyl) -amino, N- (C3-C6-Alkinyl) -N- (Ci-Cδ-alkyl) -amino, Phenyl-Ci-Cδ-alkyl, N-(Cι-C6-Al- kyl) -N- (C3.-C6-alkylsulfonyl) -amino, N- (Cι-C6-Alkyl) -N- (Cι-C6- halogenalkylsulfonyl) -amino, Heterocyclyl-Ci-Cδ-alkyl :- Ci-C δ- alkyl, and the alkyl parts of -CC 6 -alkylcarbonyl -CC-C 6 - alkyl, -C-C 6 -alkoxyimino -CC-C 6 alkyl, N- (C 3 -C 6 - Alkenyl) -N- (-C-C 6 -alkyl) -amino, N- (C 3 -C 6 -alkynyl) -N- (Ci-C δ -alkyl) -amino, phenyl-Ci-C δ -alkyl , N- (Cι-C 6 -Al- kyl) -N- (C 3 -C 6 alkylsulfonyl) amino, N- (Cι-C6 alkyl) -N- (Cι-C 6 - haloalkylsulfonyl) -amino, heterocyclyl-Ci-C δ -alkyl:
Cχ-C4-Alkyl, wie voranstehend genannt, sowie z.B. Pentyl, 1-Methylbutyl, 2-Methylbutyl, 3-Methylbutyl, 2, 2-Dimethyl- propyl, 1-Ethylpropyl, Hexyl, 1, 1-Dimethylpropyl, 1,2-Dirne - thylpropyl, 1-Methylpentyl, 2-Methylpentyl, 3-Methylpentyl, 4-Methylpentyl, 1, 1-Dimethylbutyl, 1, 2-Dimethylbutyl,Cχ-C 4 alkyl, as mentioned above, and for example pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2, 2-dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1-dimethylpropyl, 1,2 -Dirne - thylpropyl, 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-Tri- methylpropyl, 1-Ethyl-l-methylpropyl oder l-Ethyl-3-methyl- propyl ;1, 3-dimethylbutyl, 2, 2-dimethylbutyl, 2, 3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1-ethyl-l-methylpropyl or l-ethyl-3-methylpropyl;
Cχ-C -Halogenalkyl: einen Cι~C4-Alkylrest, wie vorstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder lod substituiert ist, also z.B. Chlormethyl, Dichlormethyl, Trichlormethyl, Fluormethyl, Difluormethyl, Trifluormethyl, Chlorfluormethyl, Dichlorfluormethyl, Chlor- difluormethyl, 2-Fluorethyl, 2-Chlorethyl, 2-Bromethyl, 2-Iodethyl, 2, 2-Difluorethyl, 2, 2, 2-Trifluorethyl, 2-Chlor-2-fluorethyl, 2-Chlor-2, 2-difluorethyl, 2, 2-Dichlor-2-fluorethyl, 2, 2, 2-Trichlorethyl, Pentafluor- ethyl, 2-Fluorpropyl, 3-Fluorpropyl, 2,2-Difluorpropyl,Cχ-C haloalkyl: a C ~ ~ 4 -alkyl radical, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl , Dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2, 2-difluoroethyl, 2, 2, 2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2 , 2-difluoroethyl, 2, 2-dichloro-2-fluoroethyl, 2, 2, 2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl,
2, 3-Difluorpropyl, 2-Chlorpropyl, 3-Chlorpropyl, 2,3-Dichlor- propyl, 2-Brompropyl, 3-Brompropyl, 3, 3 , 3-Trifluorpropyl, 3,3,3-Trichlorpropyl, 2 , 2 , 3 , 3 , 3-Pentafluorpropyl, Heptafluorpropyl , 1- (Fluormethyl) -2-fluorethyl, 1- (Chlormethyl) -2- chlorethyl, 1- (Brommethyl) -2-bromethyl, 4-Fluorbutyl, 4-Chlorbutyl, 4-Brombutyl oder Nonafluorbutyl;2, 3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3, 3, 3-trifluoropropyl, 3,3,3-trichloropropyl, 2, 2, 3, 3, 3-pentafluoropropyl, heptafluoropropyl, 1- (fluoromethyl) -2-fluoroethyl, 1- (chloromethyl) -2-chloroethyl, 1- (bromomethyl) -2- bromethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl;
Ci-Cß-Halogenalkyl, sowie die Halogenalkylteile von Cχ-C6-Ha- logenalkylamino, Di - (Cι-C6-halogenalkyl) amino: Cι-C4~Halogen- alkyl, wie voranstehend genannt, sowie z.B. 5-Fluorpentyl, 5-Chlorpentyl, 5-Brompentyl, 5-Iodpentyl, Undecafluorpentyl, 6-Fluorhexyl, 6-Chlorhexyl, 6-Bromhexyl, 6-Iodhexyl oder Do- decafluorhexyl ;Ci-C ß -haloalkyl, and the haloalkyl parts of Cχ-C 6 -haloalkylamino, di - (Cι-C 6 -haloalkyl) amino: Cι-C 4 ~ haloalkyl, as mentioned above, and for example 5-fluoropentyl , 5-chloropentyl, 5-bromopentyl, 5-iodopentyl, undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-iodohexyl or do- decafluorhexyl;
Cι-C4-Alkoxy: z.B. Methoxy, Ethoxy, Propoxy, 1-Methylethoxy, Butoxy, 1-Methylpropoxy, 2-Methylpropoxy oder 1, 1-Dimethyl- ethoxy;-C-C 4 alkoxy: for example methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1, 1-dimethylethoxy;
Cι-C6-Alkoxy, sowie die Alkoxyteile von Di- (Cι-C6 -alkoxy) methyl, (Ci-Cβ-Alkoxy) (Cι-C6-alkylthio) -methyl, Ci-Cδ-Alkoxy- imino-Ci-Cε-alkyl und N- (Cχ-C6-Alkoxy) -N- (Cι-C6-alkyl) -amino: Cι-C4~Alkoxy, wie voranstehend genannt, sowie z.B. Pentoxy,C 1 -C 6 -alkoxy, and the alkoxy parts of di- (C 1 -C 6 -alkoxy) methyl, (C 1 -C 6 -alkoxy) (C 1 -C 6 -alkylthio) methyl, Ci-C δ -alkoxy- imino- Ci-Cε-alkyl and N- (Cχ-C 6 -alkoxy) -N- (-C-C 6 -alkyl) -amino: Cι-C 4 ~ alkoxy, as mentioned above, and for example pentoxy,
1-Methylbutoxy, 2-Methylbutoxy, 3-Methylbutoxy, 1, 1-Dimethyl - propoxy, 1, 2-Dimethylpropoxy, 2, 2-Dimethylpropoxy, 1-Ethyl- propoxy, Hexoxy, 1-Methylpentoxy, 2-Methylpentoxy, 3-Methyl- pentoxy, 4-Methylpentoxy, 1, 1-Dimethylbutoxy, 1, 2-Dimethyl - butoxy, 1, 3-Dimethylbutoxy, 2, 2-Dimethylbutoxy, 2 , 3-Dimethyl - butoxy, 3 , 3-Dimethylbutoxy, 1-Ethylbutoxy, 2-Ethylbutoxy, 1,1, 2-Trimethylpropoxy, 1,2, 2-Trimethylpropoxy, 1-Ethyl-l-methylpropoxy oder l-Ethyl-2-methylpropoxy;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-ethyl butoxy, 1,1, 2-trimethyl propoxy, 1,2, 2-trimethyl propoxy, 1-ethyl-1-methyl propoxy or 1-ethyl-2-methyl propoxy;
Cι-C4-Halogenalkoxy: einen Cι-C4-Alkoxyrest, wie voranstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder lod substituiert ist, also z.B. Fluormethoxy, Difluormethoxy, Trifluormethoxy, Chlordifluormethoxy, Bromdi - fluormethoxy, 2-Fluorethoxy, 2-Chlorethoxy, 2-Brommethoxy, 2-Iodethoxy, 2 , 2-Difluorethoxy, 2 , 2 , 2-Trifluorethoxy,Cι-C 4 -haloalkoxy: a Cι-C4-alkoxy as mentioned above, the, chlorine, bromine / iodine or partially or completely substituted by fluorine and is substituted, eg fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, Bromdi - fluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromomethoxy, 2-iodoethoxy, 2, 2-difluoroethoxy, 2, 2, 2-trifluoroethoxy,
2-Chlor-2-fluorethoxy, 2-Chlor-2, 2-difluorethoxy, 2,2-Di- chlor-2-fluorethoxy, 2 , 2 , 2-Trichlorethoxy, Pentafluorethoxy, 2-Fluorpropoxy, 3-Fluorpropoxy, 2-Chlorpropoxy, 3-Chlor- propoxy, 2-Brompropoxy, 3-Brompropoxy, 2, 2-Difluorpropoxy, 2, 3-Difluorpropoxy, 2, 3-Dichlorpropoxy, 3 , 3, 3-Trifluorpropoxy, 3, 3, 3-Trichlorpropoxy, 2,2, 3, 3, 3-Pentafluorpropoxy, Heptafluorpropoxy, 1- (Fluormethyl) -2-fluorethoxy, 1- (Chlormethyl) -2-chlorethoxy, 1- (Brommethyl) -2-bromethoxy, 4-Fluor- butoxy, 4-Chlorbutoxy, 4-Brombutoxy oder Nonafluorbutoxy; Ci-Cß-Halogenalkoxy, sowie die Halogenalkoxyteile von Ci-Ce-Halogenalkoxy-Ci-Cδ-alkyl: Cι-C4~Halogenalkoxy, wie voranstehend genannt, sowie z.B. 5-Fluorpentoxy, 5-Chlorpent- oxy, 5-Brompentoxy, 5-Iodpentoxy, Undecafluorpentoxy, 6-Flu- orhexoxy, 6-Chlorhexoxy, 6-Bromhexoxy, 6-Iodhexoxy oder Dode- cafluorhexoxy;2-chloro-2-fluoroethoxy, 2-chloro-2, 2-difluoroethoxy, 2,2-di-chloro-2-fluoroethoxy, 2, 2, 2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2- Chloropropoxy, 3-chloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 2, 2-difluoropropoxy, 2, 3-difluoropropoxy, 2, 3-dichloropropoxy, 3, 3, 3-trifluoropropoxy, 3, 3, 3-trichloropropoxy, 2,2, 3, 3, 3-pentafluoropropoxy, heptafluoropropoxy, 1- (fluoromethyl) -2-fluoroethoxy, 1- (chloromethyl) -2-chloroethoxy, 1- (bromomethyl) -2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy; Ci-C ß -haloalkoxy, and the haloalkoxy parts of Ci-Ce-haloalkoxy-Ci-C δ- alkyl: -C-C 4 ~ haloalkoxy, as mentioned above, and for example 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy , 5-iodo-pentoxy, undecafluoropentoxy, 6-fluoro-hexoxy, 6-chloro-hexoxy, 6-bromo-hexoxy, 6-iodo-hexoxy or dodecafluoro-hexoxy;
Cι-C4-Alkylthio: z.B. Methylthio, Ethylthio, Propylthio, 1-Methylethylthio, Butylthio, 1-Methylpropylthio, 2-Methyl- propylthio oder 1, 1-Dimethylethylthio;C 1 -C 4 -Alkylthio: for example methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio or 1, 1-dimethylethylthio;
Ci-Cß-Alkylthio, sowie die Alkylthioteile von Cχ-C6-Alkyl- thio-Ci-Cδ- alkyl, Di- (Cι-C6-alkylthio)methyl und (Cι-C6-Alkoxy) - (Cι-C6-alkylthio)methyl: Cι-C4-Alkylthio, wie voranstehend genannt, sowie z.B. Pentylthio, 1-Methylbutyl- thio, 2-Methylbutylthio, 3-Methylbutylthio, 2 , 2-Dimethyl - propylthio, 1-Ethylpropylthio, Hexylthio, 1, 1-Dimethylpropyl ■ thio, 1, 2-Dimethylpropylthio, 1-Methylpentylthio, 2-Methyl- pentylthio, 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-l-methylpropylthio oder l-Ethyl-2-methylpropylthio;Ci-C ß -Alkylthio, and the alkylthio parts of Cχ-C 6 -alkyl-thio-Ci-C δ - alkyl, di- (-C-C 6 alkylthio) methyl and (-C-C 6 alkoxy) - (Cι -C 6 -alkylthio) methyl: -C-C 4 alkylthio, as mentioned above, and for example pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2, 2-dimethylpropylthio, 1-ethylpropylthio, hexylthio , 1, 1-dimethylpropyl ■ thio, 1, 2-dimethylpropylthio, 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-l-methylpropylthio or l-ethyl-2-methylpropylthio;
Ci-Cδ-Halogenalkylthio: einen Ci-Cβ-Alkylthiorest, wie voranstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder lod substituiert ist, also z.B. Fluor- methylthio, Difluormethylthio, Trifluormethylthio, Chlor- difluormethylthio, Bromdifluormethylthio, 2-Fluorethylthio, 2-Chlorethylthio, 2-Bromethylthio, 2-Iodethylthio, 2,2-Difluorethylthio, 2, 2, 2-Trifluorethylthio, 2,2,2-Tri- chlorethylthio, 2-Chlor-2-fluorethylthio, 2-Chlor-2 , 2-di- fluorethylthio, 2 , 2-Dichlor-2-fluorethylthio, Pentafluor- ethylthio, 2-Fluorpropylthio, 3-Fluorpropylthio, 2-Chlor- propylthio, 3-Chlorpropylthio, 2-Brompropylthio, 3-Brom- propylthio, 2 , 2-Difluorpropylthio, 2 , 3-Difluorpropylthio, 2 , 3-Dichlorpropylthio, 3 , 3 , 3-Trifluorpropylthio, 3,3,3-Tri- chlorpropylthio, 2, 2, 3 , 3 , 3-Pentafluorpropylthio, Heptafluor- propylthio, 1- (Fluormethyl) -2-fluorethylthio, 1- (Chlormethyl) -2-chlorethylthio, 1- (Brommethyl) -2-bromethylthio, 4-Fluorbutylthio, 4-Chlorbutyl hio, 4-Brombutylthio, Nona- fluorbutylthio, 5-Fluorpentylthio, 5-Chlorpentylthio, 5-Brom- pentylthio, 5-Iodpentylthio, Undecafluorpentylthio, 6-Fluor- hexylthio, 6-Chlorhexylthio, 6-Bromhexylthio, 6-Iodhexylthio oder Dodecafluorhexylthio; Cχ-C4-Alkylsulfinyl (Cι-C4-Alkyl-S (=0) -) : z.B. Methylsulfinyl, Ethylsulfinyl, Propylsulfinyl, 1-Methylethylsulfinyl, Butyl- sulfinyl, 1-Methylpropylsulfinyl, 2-Methylpropylsulfinyl oder 1, 1-Dimethylethylsulfinyl;Ci-C δ -haloalkylthio: a Ci-Cβ-alkylthio radical, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio , 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2, 2, 2-trifluoroethylthio, 2,2,2-trichloroethylthio, 2-chloro-2-fluoroethylthio, 2 -Chlor-2, 2-di-fluoroethylthio, 2, 2-dichloro-2-fluoroethylthio, pentafluoroethylthio, 2-fluoropropylthio, 3-fluoropropylthio, 2-chloropropylthio, 3-chloropropylthio, 2-bromopropylthio, 3-bromo - propylthio, 2, 2-difluoropropylthio, 2, 3-difluoropropylthio, 2, 3-dichloropropylthio, 3, 3, 3-trifluoropropylthio, 3,3,3-trichloropropylthio, 2, 2, 3, 3, 3-pentafluoropropylthio , Heptafluoropropylthio, 1- (fluoromethyl) -2-fluoroethylthio, 1- (chloromethyl) -2-chloroethylthio, 1- (bromomethyl) -2-bromomethylthio, 4-fluorobutylthio, 4-chlorobutyl hio, 4-Br ombutylthio, non-fluorobutylthio, 5-fluoropentylthio, 5-chloropentylthio, 5-bromopentylthio, 5-iodopentylthio, undecafluoropentylthio, 6-fluoro-hexylthio, 6-chlorohexylthio, 6-bromohexylthio, 6-iodohexylaflio or dio; Cχ-C 4 -Alkylsulfinyl (-C-C 4 -alkyl-S (= 0) -): e.g. methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl or 1, 1-dimethylethylsulfinyl ;
Cι-C6 -Alkylsulfinyl sowie die Alkylsulfinyl este von Ci -C6-Alkylsulfinyl -Ci-Cß-alkyl: Cχ-C4 -Alkylsulfinyl, wie voranstehend genannt, sowie z.B. Pentylsulfinyl, 1-Methylbutylsulfinyl, 2-Methylbutylsulfinyl, 3-Methylbutylsulfinyl, 2 , 2-Dimethyl- propylsulfinyl, 1-Ethylpropylsulfinyl, 1, 1-Dimethylpropylsul- finyl, 1, 2-Dimethylpropylsulfinyl, Hexylsulfinyl, 1-Methyl - pentylsulfinyl, 2-Methylpentylsulfinyl, 3-Methylpe tylsulfi- nyl, 4-Methylpentylsulfinyl, 1, 1-Dimethylbutylsulfinyl, 1, 2-Dimethylbutylsulfinyl, 1, 3-Dimethylbutylsulfinyl, 2,2-Di- methylbutylsulfinyl, 2, 3-Dimethylbutylsulfinyl, 3 , 3-Dimethylbutylsulfinyl, 1-Ethylbutylsulfinyl, 2-Ethylbutylsulfinyl , 1, 1,2-Trimethylpropylsulfinyl, 1, 2 , 2-Trimethylpropylsulfinyl, 1-Ethyl-l-methylpropylsulfinyl oder l-Ethyl-2-methylpropyl - sulfinyl;C 1 -C 6 -alkylsulfinyl and the alkylsulfinyl esters of C 1 -C 6 -alkylsulfinyl-Ci-C ß- alkyl: Cχ-C 4 -alkylsulfinyl, as mentioned above, and for example pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3- Methylbutylsulfinyl, 2, 2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, 1, 1-dimethylpropylsulfinyl, 1, 2-dimethylpropylsulfinyl, hexylsulfinyl, 1-methyl-pentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinylnyl , 1, 1-dimethylbutylsulfinyl, 1, 2-dimethylbutylsulfinyl, 1, 3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2, 3-dimethylbutylsulfinyl, 3, 3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl , 2-trimethylpropylsulfinyl, 1, 2, 2-trimethylpropylsulfinyl, 1-ethyl-l-methylpropylsulfinyl or l-ethyl-2-methylpropylsulfinyl;
Ci-Cδ-Halogenalkylsulfinyl: Ci-Cε-Alkylsulfinylrest, wie voranstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder lod substituiert ist, also z.B. Fluormethylsulfinyl, Difluormethylsulfinyl, Trifluormethyl - sulfinyl, Chlordifluormethylsulfinyl, Bromdifluormethylsulfi- nyl, 2-Fluorethylsulfinyl, 2-Chlorethylsulfinyl, 2-Bromethyl- sulfinyl, 2-Iodethylsulfinyl, 2,2-Difluorethylsulfinyl, 2,2, 2-Trifluorethylsulfinyl , 2,2, 2-Trichlorethylsulfinyl , 2-Chlor-2-fluorethylsulfinyl , 2-Chlor-2 , 2-difluorethylsulfi - nyl, 2 , 2-Dichlor-2-fluorethylsulfinyl, Pentafluorethylsulfi- nyl, 2-Fluorpropylsulfinyl, 3-Fluorpropylsulfinyl , 2-Chlor- propylsulfinyl, 3-Chlorpropylsulfinyl, 2-Brompropylsulfinyl, 3-Brompropylsulfinyl, 2, 2-Difluorpropylsulfinyl, 2,3-Difluor- propylsulfinyl, 2, 3-Dichlorpropylsulfinyl, 3 , 3, 3-Trifluorpro- pylsulfinyl, 3 , 3 , 3-Trichlorpropylsulfinyl, 2, 2, 3, 3, 3-Penta- fluorpropylsulfinyl, Heptafluorpropylsulfinyl, 1- (Fluormethyl) -2-fluorethylsulfinyl, 1- (Chlormethyl) -2-chlorethyl- sulfinyl, 1- (Brommethyl) -2-bromethylsulfinyl, 4-Fluorbutyl- sulfinyl, 4-Chlorbutylsulfinyl, 4-Brombutylsulfinyl, Nona- fluorbutylsulfinyl, 5-Fluorpentylsulfinyl, 5-Chlorpentylsul- finyl, 5-Brompentylsulfinyl, 5-Iodpentylsulfinyl, Undeca- fluorpentylsulfinyl, 6-Fluorhexylsulfinyl, 6-Chlorhexyl- sulfinyl, 6-Bromhexylsulfinyl, 6-Iodhexylsulfinyl oder Dodecafluorhexy1sulfinyl; C1-C4-Alkylsulfonyl (Cι-C4-Alkyl-S (=0) 2-) : z.B. Methylsulfonyl, Ethylsulfonyl, Propylsulfonyl, 1-Methylethyl- sulfonyl, Butylsulfonyl, 1-Methylpropylsulfonyl, 2-Methyl- propylsulfonyl oder 1, 1-Dimethylethylsulfonyl;Ci-C δ -haloalkylsulfinyl: Ci-Cε-alkylsulfinyl radical, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example fluoromethylsulfinyl, difluoromethylsulfinyl, trifluoromethylsulfinyl, chlorodifluoromethylsulfinyl, bromodifluoromethylsulfonyl 2-fluoroethylsulfinyl, 2-chloroethylsulfinyl, 2-bromoethylsulfinyl, 2-iodoethylsulfinyl, 2,2-difluoroethylsulfinyl, 2,2, 2-trifluoroethylsulfinyl, 2,2, 2-trichloroethylsulfinyl, 2-chloro-2-fluoroethylsulfinyl, 2- Chloro-2, 2-difluoroethylsulfinyl, 2, 2-dichloro-2-fluoroethylsulfinyl, pentafluoroethylsulfinyl, 2-fluoropropylsulfinyl, 3-fluoropropylsulfinyl, 2-chloropropylsulfinyl, 3-chloropropylsulfinyl, 2-bromopropylsulfinyl, 3-bromopropyl 2, 2-difluoropropylsulfinyl, 2,3-difluoropropylsulfinyl, 2, 3-dichloropropylsulfinyl, 3, 3, 3-trifluoropropylsulfinyl, 3, 3, 3-trichloropropylsulfinyl, 2, 2, 3, 3, 3-penta- fluoropropylsulfinyl, heptafluoropropylsulfinyl, 1- (fluoromethyl) -2-fluorine ethylsulfinyl, 1- (chloromethyl) -2-chloroethylsulfinyl, 1- (bromomethyl) -2-bromethylsulfinyl, 4-fluorobutylsulfinyl, 4-chlorobutylsulfinyl, 4-bromobutylsulfinyl, non-fluorobutylsulfinyl, 5-fluoropentylsulfinyl, 5-chloropentylsulfinyl finyl, 5-bromopentylsulfinyl, 5-iodopentylsulfinyl, undeca- fluoropentylsulfinyl, 6-fluorohexylsulfinyl, 6-chlorohexylsulfinyl, 6-bromohexylsulfinyl, 6-iodohexylsulfinyl or dodecafluorhexylsulfinyl; C 1 -C 4 -Alkylsulfonyl (-C-C 4 -alkyl-S (= 0) 2 -): e.g. methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl or 1 , 1-dimethylethylsulfonyl;
Ci-Cβ -Alkylsulfonyl, sowie die Alkylsulfonylreste von Cι-C6-Alkylsulfonyl-Cι-C6-alkyl, Cι-C6-Alkylsulfonyl -amino und N- (Cι-C6-Alkyl) -N- (Cι-C6-alkylsulfonyl) amino: Cι-C4-Alkylsul- fonyl wie voranstehend genannt, sowie Pentylsulfonyl, 1-Methylbutylsulfonyl, 2-Methylbutylsulfonyl, 3-Methylbutylsulfonyl, 1, 1-Dimethylpropylsulfonyl, 1, 2-Dimethylpropyl- sulfonyl, 2 , 2-Dimethylpropylsulfonyl, 1-Ethylpropylsulfonyl, Hexylsulfonyl, 1-Methylpentylsulfonyl, 2-Methylpentyl- sulfonyl, 3-Methylpentylsulfonyl, 4-Methylpentylsulfonyl, 1, 1-Dimethylbutylsulfonyl, 1, 2-Dimethylbutylsulfonyl ,Ci-Cβ-alkylsulfonyl, and the alkylsulfonyl radicals of Cι-C 6 -alkylsulfonyl-Cι-C 6 -alkyl, Cι-C 6 -alkylsulfonyl -amino and N- (-Cι-C 6 alkyl) -N- (Cι-C 6- alkylsulfonyl) amino: -CC 4 -alkylsulfonyl as mentioned above, and pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1, 1-dimethylpropylsulfonyl, 1, 2-dimethylpropylsulfonyl -Dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 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-Trimethyl- propylsulfonyl , 1,2, 2-Trimethylpropylsulfonyl , 1-Ethyl-l-methylpropylsulfonyl oder l-Ethyl-2-methylpropyl- sulfonyl;1, 3-dimethylbutylsulfonyl, 2, 2-dimethylbutylsulfonyl, 2, 3-dimethylbutylsulfonyl, 3, 3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1, 1, 2-trimethylpropylsulfonyl, 1,2 1-ethyl-l-methylpropylsulfonyl or l-ethyl-2-methylpropylsulfonyl;
Ci-Cδ-Halogenalkylsulfonyl, sowie die Halogenalkylreste von N- (Cι-C6-Halogenalkylsulfonyl) -amino und N- (Cx-Cε-Alkyl) -N- (Ci-Cδ-halogenalkylsulfonyl) -amino: einen Cι-C6-Alkylsulfonyl- rest, wie voranstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder lod substituiert ist, also z.B. Fluormethylsulfonyl, Difluormethylsulfonyl , Trifluor- methylsulfonyl, Chlordifluormethylsulfonyl, Bromdifluorme- thylsulfonyl, 2-Fluorethylsulfonyl , 2-Chlorethylsulfonyl,Ci-C δ -haloalkylsulfonyl, and the haloalkyl residues of N- (Cι-C 6 -haloalkylsulfonyl) -amino and N- (Cx-Cε-alkyl) -N- (Ci-C δ -haloalkylsulfonyl) -amino: a Cι- C 6 -alkylsulfonyl radical, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example fluoromethylsulfonyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethyl-2-sulfonyl, 2-fluorosulfonyl Chloroethylsulfonyl,
2-Bromethylsulfonyl, 2-Iodethylsulfonyl, 2 , 2-Difluorethylsul - fonyl, 2, 2, 2-Trifluorethylsulfonyl, 2-Chlor-2-fluorethylsul - fonyl, 2-Chlor-2,2-difluorethylsulfonyl, 2, 2-Dichlor-2-fluorethylsulfonyl, 2, 2, 2-Trichlorethylsulfonyl, Pentafluorethyl - sulfonyl, 2-Fluorpropylsulfonyl , 3-Fluorpropylsulfonyl ,2-bromoethylsulfonyl, 2-iodoethylsulfonyl, 2, 2-difluoroethylsulfonyl, 2, 2, 2-trifluoroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl, 2-chloro-2,2-difluoroethylsulfonyl, 2, 2-dichloro- 2-fluoroethylsulfonyl, 2, 2, 2-trichloroethylsulfonyl, pentafluoroethylsulfonyl, 2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl,
2-Chlorpropylsulfonyl, 3-Chlorpropylsulfonyl, 2-Brompropyl- sulfonyl, 3-Brompropylsulfonyl, 2, 2-Difluorpropylsulfonyl,2-chloropropylsulfonyl, 3-chloropropylsulfonyl, 2-bromopropylsulfonyl, 3-bromopropylsulfonyl, 2, 2-difluoropropylsulfonyl,
2, 3-Difluorpropylsulfonyl, 2, 3-Dichlorpropylsulfonyl,2,3-difluoropropylsulfonyl, 2,3-dichloropropylsulfonyl,
3,3, 3-Trifluorpropylsulfonyl, 3,3, 3-Trichlorpropylsulfonyl, 2, 2, 3, 3, 3-Pentafluorpropylsulfonyl, Heptafluorpropylsulfonyl, 1- (Fluormethyl) -2-fluorethylsulfonyl, 1- (Chlormethyl) -2- chlorethylsulfonyl, 1- (Brommethyl) -2-bromethylsulfonyl, 4-Fluorbutylsulfonyl, 4-Chlorbutylsulfonyl, 4-Brombutylsulfo- nyl, Nonafluorbutylsulfonyl, 5-Fluorpentylsulfonyl, 5-Chlor- pentylsulfonyl, 5-Brompentylsulfonyl, 5-Iodpentylsulfonyl, 6-Fluorhexylsulfonyl, 6-Bromhexylsulfonyl, 6-Iodhexylsulfonyl oder Dodecafluorhexylsulfonyl;3,3,3-trifluoropropylsulfonyl, 3,3,3-trichloropropylsulfonyl, 2, 2, 3, 3, 3-pentafluoropropylsulfonyl, heptafluoropropylsulfonyl, 1- (fluoromethyl) -2-fluoroethylsulfonyl, 1- (chloromethyl) -2-chloroethylsulfonyl, 1- (bromomethyl) -2-bromomethylsulfonyl, 4-fluorobutylsulfonyl, 4-chlorobutylsulfonyl, 4-bromobutylsulfonyl, nonafluorobutylsulfonyl, 5-fluoropentylsulfonyl, 5-chloropentylsulfonyl, 5-bromopentylsulfonylsulfonyl, 5 6-fluorohexylsulfonyl, 6-bromohexylsulfonyl, 6-iodohexylsulfonyl or dodecafluorohexylsulfonyl;
Ci-Cδ-Alkylamino, sowie die Alkylaminoreste von (Ci-Cß- Alkoxy) (Cι-C6-alkyl) amino, also z.B. Methylamino, Ethylamino, Propylamino, 1-Methylethylamino, Butylamino, 1-Methylpropyl- amino, 2-Methylpropylamino, 1, 1-Dimethylethylamino, Pentyl- amino, 1-Methylbutylamino, 2-Methylbutylamino, 3-Methylbutyl- amino, 2, 2-Dimethylpropylamino, 1-Ethylpropylamino, Hexyl- amino, 1, 1-Dimethylpropylamino, 1, 2-Dimethylpropylamino, 1-Methylpentylamino, 2-Methylpentylamino, 3-Methylpentyl- amino, 4-Methylpentylamino, 1, 1-Dimethylbutylamino, 1, 2-Dimethylbutylamino, 1, 3-Dimethylbutylamino, 2 , 2-Dimethyl- butylamino, 2, 3-Dimethylbutylamino, 3 , 3-Dimethylbutylamino, 1-Ethylbutylamino, 2-Ethylbutylamino, 1, 1, 2-Trimethylpropyl - amino, 1, 2, 2-Trimethylpropylamino, 1-Ethyl-l-methylpropyl- amino oder l-Ethyl-2-methylpropylamino;Ci-C δ- alkylamino, and the alkylamino residues of (Ci-C ß -alkoxy) (-C-C 6 -alkyl) amino, for example methylamino, ethylamino, propylamino, 1-methylethylamino, butylamino, 1-methylpropylamino, 2 -Methylpropylamino, 1, 1-dimethylethylamino, pentylamino, 1-methylbutylamino, 2-methylbutylamino, 3-methylbutylamino, 2, 2-dimethylpropylamino, 1-ethylpropylamino, hexylamino, 1, 1-dimethylpropylamino, 1, 2 -Dimethylpropylamino, 1-methylpentylamino, 2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino, 1, 1-dimethylbutylamino, 1, 2-dimethylbutylamino, 1, 3-dimethylbutylamino, 2, 2-dimethylbutylamino, 2, 3 -Dimethylbutylamino, 3, 3-dimethylbutylamino, 1-ethylbutylamino, 2-ethylbutylamino, 1, 1, 2-trimethylpropylamino, 1, 2, 2-trimethylpropylamino, 1-ethyl-l-methylpropylamino or l-ethyl-2 -methylpropylamino;
(Cι-C6-Alkylamino) sulfonyl : z.B. Methylaminosulfonyl, Ethyl - aminosulfonyl, Propylaminosulfonyl, 1-Methylethylaminosulfonyl, Butylaminosulfonyl, 1-Methylpropylaminosulfonyl, 2-Methylpropylaminosulfonyl , 1, 1-Dimethylethylaminosulfonyl , Pentylaminosulfonyl, 1-Methylbutylaminosulfonyl, 2-Methylbu- tylaminosulfonyl, 3-Methylbutylaminosulfonyl, 2, 2-Dimethyl- propylaminosulfonyl, 1-Ethylpropylaminosulfonyl, Hexylamino- sulfonyl, 1, 1-Dimethylpropylaminosulfonyl, 1,2-Dirnethylpro- pylaminosulfonyl, 1-Methylpentylaminosulfonyl, 2-Methylpen- tylaminosulfonyl, 3-Methylpentylaminosulfonyl, 4-Methylpen- tylaminosulfonyl, 1, 1-Dimethylbutylaminosulfonyl, 1,2-Dime- thylbutylaminosulfonyl, 1, 3-Dimethylbutylaminosulfonyl,(-C-C 6 -Alkylamino) sulfonyl: for example methylaminosulfonyl, ethyl-aminosulfonyl, propylaminosulfonyl, 1-methylethylaminosulfonyl, butylaminosulfonyl, 1-methylpropylaminosulfonyl, 2-methylpropylaminosulfonyl, 1, 1-dimethylethylaminosulfonyl, 2-methyl-aminosulfonyl, methyl , 3-Methylbutylaminosulfonyl, 2, 2-Dimethylpropylaminosulfonyl, 1-Ethylpropylaminosulfonyl, Hexylaminosulfonyl, 1, 1-Dimethylpropylaminosulfonyl, 1,2-Dirnethylpro- pylaminosulfonyl, 1-Methylpentylaminosulfonyl, 2-Methylpenyl- 4-Methylpen- tyl -Methylpentylaminosulfonyl, 1, 1-dimethylbutylaminosulfonyl, 1,2-dimethylbutylaminosulfonyl, 1, 3-dimethylbutylaminosulfonyl,
2 , 2-Dimethylbutylaminosulfonyl, 2, 3-Dimethylbutylaminosulfo- nyl, 3 , 3-Dimethylbutylaminosulfonyl, 1-Ethylbutylaminosulfo- nyl, 2-Ethylbutylaminosulfonyl, 1, 1, 2-Trimethylpropylamino- sulfonyl, 1, 2, 2-Trimethylpropylaminosulfonyl, 1-Ethyl-l-me- thylpropylaminosulfonyl oder l-Ethyl-2-methylpropylaminosul- fonyl;2, 2-dimethylbutylaminosulfonyl, 2, 3-dimethylbutylaminosulfonyl, 3, 3-dimethylbutylaminosulfonyl, 1-ethylbutylaminosulfonyl, 2-ethylbutylaminosulfonyl, 1, 1, 2-trimethylpropylaminosulfonyl, 1, 2, 1, 2, 1, 2-trimethyl Ethyl-l-methylpropylaminosulfonyl or l-ethyl-2-methylpropylaminosulfonyl;
Di- (Cι-C6-alkyl) -aminosulfonyl : z.B. N,N-Dimethylaminosulfo- nyl, N,N-Diethylaminosulfonyl, N,N-Di- (1-methylethyl) amino- sulfonyl, N,N-Dipropylaminosulfonyl, N,N-Dibutylaminosulfo- nyl, N,N-Di- (1-methylpropyl) -aminosulfonyl, N,N-Di- (2-methyl - propyl) -aminosulfonyl, N,N-Di- (1, 1-dimethylethyl) -aminosulfonyl, N-Ethyl-N-methylaminosulfonyl, N-Methyl-N-propyl- aminosulfonyl, N-Methyl-N- (1-methylethyl) -aminosulfonyl, N-Butyl-N-methylaminosulfonyl, N-Methyl-N- (1-methyl - propyl) -aminosulfonyl, N-Methyl-N- (2-methylpropyl) -aminosulfonyl , N- (1, 1-Dimethylethyl) -N-methylaminosulfonyl , N-Ethyl-N-propylaminosulfonyl , N-Ethyl-N- (1-methyl - ethyl) -aminosulfonyl, N-Butyl-N-ethylaminosulfonyl, N- Ethyl-N- (1-methylpropyl) -aminosulfonyl, N-Ethyl-N- (2-methyl - propyl) -aminosulfonyl, N-Ethyl-N- (1, 1-dimethylethyl) -amino- sulfonyl, N- (1-Methylethyl) -N-propylaminosulfonyl, N-Butyl- N-propylaminosulfonyl, N- (1-Methylpropyl) -N-propylaminosulfonyl, N- (2-Methylpropyl) -N-propylaminosulfonyl, N- (1, 1-Dimethylethyl) -N-propylaminosulfonyl, N-Butyl-N- (1-methylethyl) -aminosulfonyl, N- (1-Methylethyl) -N- (1-methyl - propyl) -aminosulfonyl, N- (1-Methylethyl) -N- (2-methyl - propyl) -aminosulfonyl , N- (1 , 1-Dimethylethyl) -N- (1-methyl - ethyl) -aminosulfonyl, N-Butyl-N- (1-methylpropyl) -aminosulfonyl, N-Butyl-N- (2-methylpropyl) -aminosulfonyl, N- Butyl-N- (1 , 1-dimethylethyl) -aminosulfonyl , N- (1-Methyl - propyl) -N- (2-methylpropyl) -aminosulfonyl, N- (1, 1-Dimethylethyl) -N- (1-methylpropyl) -aminosulfonyl , N- (1 , 1-Dimethyl - ethyl) -N- (2-methylpropyl) -aminosulfonyl, N-Methyl-N-pentylaminosulfonyl, N-Methyl-N- (1-methylbutyl) -aminosulfonyl, N-Methyl-N- (2-methylbutyl) -aminosulfonyl, N-Methyl-N- (3-methyl- butyl) -aminosulfonyl, N-Methyl-N- (2, 2-dimethylpropyl) -aminosulfonyl, N-Methyl-N- (1-ethylpropyl) -aminosulfonyl, N-Methyl- N-hexylaminosulfonyl, N-Methyl-N- (1, 1-dimethylpropyl) -aminosulfonyl , N-Methyl-N- (1, 2-dimethylpropyl) -aminosulfonyl , N-Methyl-N- (1-methylpentyl) -aminosulfonyl, N-Methyl-N- (2- methylpentyl) -aminosulfonyl, N-Methyl-N- (3-methylpentyl) - aminosulfonyl, N-Methyl-N- (4-methylpentyl) -aminosulfonyl, N-Methyl-N- (1 , 1-dimethylbutyl) -aminosulfonyl , N-Methyl-N- (1,2-dimethylbutyl) -aminosulfonyl, N-Methyl-N- (1, 3-dimethyl- butyl) -aminosulfonyl, N-Methyl-N- (2, 2-dimethylbutyl) -amino- sulfonyl, N-Methyl-N- (2, 3-dimethylbutyl) -aminosulfonyl, N-Methyl-N- (3 , 3-dimethylbutyl) -aminosulfonyl, N-Methyl-N- (1- ethylbutyl) -aminosulfonyl, N-Methyl-N- (2-ethylbutyl) -aminosulfonyl, N-Methyl-N- (1,1, 2-trimethylpropyl) -aminosulfonyl, N-Methyl-N- (1, 2 , 2-trimethylpropyl) -aminosulfonyl, N-Methyl-N- (1-ethyl-l-methylpropyl) -aminosulfonyl, N-Methyl-N- (1-ethyl- 2-methylpropyl) -aminosulfonyl, N-Ethyl-N-pentylaminosulfonyl, N-Ethyl-N- (1-methylbutyl) -aminosulfonyl , N-Ethyl-N- (2-methyl - butyl) -aminosulfonyl, N-Ethyl-N- (3-methylbutyl) -aminosulfonyl, N-Ethyl-N- (2, 2-dimethylpropyl) -aminosulfonyl, N- Ethyl-N- (1-ethylpropyl) -aminosulfonyl, N-Ethyl-N-hexylamino- sulfonyl , N-Ethyl-N- (1 , 1-dimethylpropyl) -aminosulfonyl , N- Ethyl-N- (1, 2-dimethylpropyl) -aminosulfonyl, N-Ethyl-N- (1-methylpentyl) -aminosulfonyl, N-Ethyl-N- (2-methyl - pentyl) -aminosulfonyl, N-Ethyl-N- (3-methylpentyl) -amino- sulfonyl, N-Ethyl-N- (4-methylpentyl) -aminosulfonyl,Di- (-C 6 -alkyl) -aminosulfonyl: for example N, N-dimethylaminosulfonyl, N, N-diethylaminosulfonyl, N, N-di- (1-methylethyl) aminosulfonyl, N, N-dipropylaminosulfonyl, N , N-Dibutylaminosulfonyl, N, N-Di- (1-methylpropyl) -aminosulfonyl, N, N-Di- (2-methyl-propyl) -aminosulfonyl, N, N-Di- (1, 1-dimethylethyl) -aminosulfonyl, N-ethyl-N-methylaminosulfonyl, N-methyl-N-propylaminosulfonyl, N-methyl-N- (1-methylethyl) -aminosulfonyl, N-butyl-N-methylaminosulfonyl, N-methyl-N- ( 1-methyl-propyl) -aminosulfonyl, N-methyl-N- (2-methylpropyl) -aminosulfonyl, N- (1, 1-dimethylethyl) -N-methylaminosulfonyl, N-ethyl-N-propylaminosulfonyl, N-ethyl-N- (1-methyl-ethyl) -aminosulfonyl, N-butyl-N-ethylaminosulfonyl, N-ethyl-N- (1-methylpropyl) -aminosulfonyl, N-ethyl- N- (2-methyl-propyl) -aminosulfonyl, N-ethyl-N- (1,1-dimethylethyl) -aminosulfonyl, N- (1-methylethyl) -N-propylaminosulfonyl, N-butyl-N-propylaminosulfonyl, N- (1-methylpropyl) -N-propylaminosulfonyl, N- (2-methylpropyl) -N-propylaminosulfonyl, N- (1, 1-dimethylethyl) -N-propylaminosulfonyl, N-butyl-N- (1-methylethyl) - aminosulfonyl, N- (1-methylethyl) -N- (1-methyl-propyl) -aminosulfonyl, N- (1-methylethyl) -N- (2-methyl-propyl) -aminosulfonyl, N- (1, 1-dimethylethyl ) -N- (1-methyl-ethyl) -aminosulfonyl, N-butyl-N- (1-methylpropyl) -aminosulfonyl, N-butyl-N- (2-methylpropyl) -aminosulfonyl, N-butyl-N- (1 , 1-dimethylethyl) aminosulfonyl, N- (1-methylpropyl) -N- (2-methylpropyl) aminosulfonyl, N- (1, 1-dimethylethyl) -N- (1-methylpropyl) aminosulfonyl, N- (1, 1-dimethyl-ethyl) -N- (2-methylpropyl) -am inosulfonyl, N-methyl-N-pentylaminosulfonyl, N-methyl-N- (1-methylbutyl) aminosulfonyl, N-methyl-N- (2-methylbutyl) aminosulfonyl, N-methyl-N- (3-methylbutyl) ) -aminosulfonyl, N-methyl-N- (2,2-dimethylpropyl) -aminosulfonyl, N-methyl-N- (1-ethylpropyl) -aminosulfonyl, N-methyl-N-hexylaminosulfonyl, N-methyl-N- (1st , 1-dimethylpropyl) aminosulfonyl, N-methyl-N- (1, 2-dimethylpropyl) aminosulfonyl, N-methyl-N- (1-methylpentyl) aminosulfonyl, N-methyl-N- (2-methylpentyl) - aminosulfonyl, N-methyl-N- (3-methylpentyl) aminosulfonyl, N-methyl-N- (4-methylpentyl) aminosulfonyl, N-methyl-N- (1, 1-dimethylbutyl) aminosulfonyl, N-methyl N- (1,2-dimethylbutyl) aminosulfonyl, N-methyl-N- (1, 3-dimethylbutyl) aminosulfonyl, N-methyl-N- (2, 2-dimethylbutyl) aminosulfonyl, N- Methyl-N- (2,3-dimethylbutyl) aminosulfonyl, N-methyl-N- (3,3-dimethylbutyl) aminosulfonyl, N-methyl-N- (1-ethylbutyl) aminosulfonyl, N-methyl-N- (2-ethylbutyl) aminosulfonyl, N-methyl-N- (1,1, 2-trim ethylpropyl) aminosulfonyl, N-methyl-N- (1, 2, 2-trimethylpropyl) aminosulfonyl, N-methyl-N- (1-ethyl-l-methylpropyl) aminosulfonyl, N-methyl-N- (1- ethyl 2-methylpropyl) aminosulfonyl, N-ethyl-N-pentylaminosulfonyl, N-ethyl-N- (1-methylbutyl) aminosulfonyl, N-ethyl-N- (2-methylbutyl) aminosulfonyl, N-ethyl -N- (3-methylbutyl) aminosulfonyl, N-ethyl-N- (2,2-dimethylpropyl) aminosulfonyl, N-ethyl-N- (1-ethylpropyl) aminosulfonyl, N-ethyl-N-hexylaminosulfonyl , N-ethyl-N- (1, 1-dimethylpropyl) aminosulfonyl, N-ethyl-N- (1, 2-dimethylpropyl) aminosulfonyl, N-ethyl-N- (1-methylpentyl) aminosulfonyl, N-ethyl -N- (2-methyl-pentyl) -aminosulfonyl, N-ethyl-N- (3-methylpentyl) -aminosulfonyl, N-ethyl-N- (4-methylpentyl) -aminosulfonyl,
N-Ethyl-N- (1, 1-dimethylbutyl) -aminosulfonyl, N-Ethyl-N- (1, 2-dimethylbutyl) -aminosulfonyl, N-Ethyl-N- (1, 3-dimethyl- butyl) -aminosulfonyl, N-Ethyl-N- (2, 2-dimethylbutyl) -aminosulfonyl, N-Ethyl-N- (2, 3-dimethylbutyl) -aminosulfonyl, N- Ethyl-N- (3, 3-dimethylbutyl) -aminosulfonyl, N-Ethyl-N-N-ethyl-N- (1, 1-dimethylbutyl) aminosulfonyl, N-ethyl-N- (1, 2-dimethylbutyl) aminosulfonyl, N-ethyl-N- (1, 3-dimethyl- butyl) aminosulfonyl, N-ethyl-N- (2,2-dimethylbutyl) -aminosulfonyl, N-ethyl-N- (2,3-dimethylbutyl) -aminosulfonyl, N-ethyl-N- (3,3-dimethylbutyl) -aminosulfonyl, N-ethyl-N-
(1-ethylbutyl) -aminosulfonyl, N-Ethyl-N- (2-ethylbutyl) -amino- sulfonyl, N-Ethyl-N- (1, 1, 2-trimethylpropyl) -aminosulfonyl, N- Ethyl-N- (1,2, 2-trimethylpropyl) -aminosulfonyl, N-Ethyl-N-(1-ethylbutyl) aminosulfonyl, N-ethyl-N- (2-ethylbutyl) aminosulfonyl, N-ethyl-N- (1, 1, 2-trimethylpropyl) aminosulfonyl, N-ethyl-N- (1 , 2,2-trimethylpropyl) aminosulfonyl, N-ethyl-N-
(1-ethyl-l-methylpropyl) -aminosulfonyl, N-Ethyl-N- (1-ethyl- 2-methylpropyl) -aminosulfonyl, N-Propyl-N-pentylaminosulfo- nyl, N-Butyl-N-pentylaminosulfonyl, N, N-Dipentylaminosulfo- nyl, N-Propyl-N-hexylaminosulfonyl, N-Butyl-N-hexylaminosul- fonyl, N-Pentyl-N-hexylaminosulfonyl oder N,N-Dihexylamino- sulfonyl;(1-ethyl-l-methylpropyl) aminosulfonyl, N-ethyl-N- (1-ethyl-2-methylpropyl) aminosulfonyl, N-propyl-N-pentylaminosulfonyl, N-butyl-N-pentylaminosulfonyl, N, N-dipentylaminosulfonyl, N-propyl-N-hexylaminosulfonyl, N-butyl-N-hexylaminosulfonyl, N-pentyl-N-hexylaminosulfonyl or N, N-dihexylaminosulfonyl;
Di- (Cι-C4~alkyl) amino, sowie die Dialkylaminoreste von Di- (Cι-C4~alkyl) amino-Cι-C4-alkoxycarbonyl, also z.B. N,N-Di- methylamino, N,N-Diethylamino, N,N-Dipropylamino, N,N-Di- (1-methylethyl) -amino, N,N-Dibutylamino, N, N-Di- (1-methylpropyl) amino, N, N-Di- (2-methylpropyl) amino, N,N-Di- (1, 1-dimethylethyl) -amino, N-Ethyl-N-methylamino, N-Methyl-N-propylamino, N-Methyl-N- (1-methylethyl) amino, N-Butyl-N-methylamino, N-Methyl-N- (1-methylpropyl) amino, N-Methyl-N- (2-methylpropyl) amino, N- (1, 1-Dimethylethyl) -N- methylamino, N-Ethyl-N-propylamino, N-Ethyl-N- (1-methylethyl) amino, N-Butyl-N-ethylamino, N-Ethyl-N- (1-methyl - propyl) amino, N-Ethyl-N- (2-methylpropyl) amino, N-Ethyl-N- (1, 1-dimethylethyl) amino, N- (1-Methylethyl) -N-propylamino, N-Butyl-N-propylamino, N- (1-Methylpropyl) -N-propylamino, N- (2-Methylpropyl) -N-propylamino, N- (1, 1-Dimethylethyl) -N- propylamino, N-Butyl-N- (1-methylethyl) amino, N-(1-Methyl- ethyl) -N- (1-methylpropyl) amino, N- (1-Methylethyl) -N-Di- (-C 4 ~ alkyl) amino, and the dialkylamino residues of di- (-C 4 ~ alkyl) amino -CC-C 4 -alkoxycarbonyl, so for example N, N-dimethylamino, N, N-diethylamino , N, N-dipropylamino, N, N-di- (1-methylethyl) amino, N, N-dibutylamino, N, N-di- (1-methylpropyl) amino, N, N-di- (2-methylpropyl ) amino, N, N-di- (1, 1-dimethylethyl) amino, N-ethyl-N-methylamino, N-methyl-N-propylamino, N-methyl-N- (1-methylethyl) amino, N- Butyl-N-methylamino, N-methyl-N- (1-methylpropyl) amino, N-methyl-N- (2-methylpropyl) amino, N- (1, 1-dimethylethyl) -N-methylamino, N-ethyl- N-propylamino, N-ethyl-N- (1-methylethyl) amino, N-butyl-N-ethylamino, N-ethyl-N- (1-methylpropyl) amino, N-ethyl-N- (2-methylpropyl ) amino, N-ethyl-N- (1, 1-dimethylethyl) amino, N- (1-methylethyl) -N-propylamino, N-butyl-N-propylamino, N- (1-methylpropyl) -N-propylamino, N- (2-methylpropyl) -N-propylamino, N- (1, 1-dimethylethyl) -N-propylamino, N-butyl-N- (1-methylethyl) amino, N- (1-methylethyl) -N - (1-methylpropyl) amino, N- (1-M ethylethyl) -N-
(2-methylpropyl) mino, N- (1, 1-Dimethylethyl) -N- (1-methylethyl) amino, N-Butyl-N- (1-methylpropyl) -amino, N-Butyl-N- (2-methylpropyl) amino, N-Butyl-N- (1, 1-dimethyl - ethyl) amino, N- (1-Methylpropyl) -N- (2-methylpropyl) -amino, N- (1, 1-Dimethylethyl) -N- (1-methylpropyl) -amino oder N- (1, 1-Dimethylethyl) -N- (2-methylpropyl) amino;(2-methylpropyl) mino, N- (1, 1-dimethylethyl) -N- (1-methylethyl) amino, N-butyl-N- (1-methylpropyl) amino, N-butyl-N- (2-methylpropyl ) amino, N-butyl-N- (1, 1-dimethylethyl) amino, N- (1-methylpropyl) -N- (2-methylpropyl) amino, N- (1, 1-dimethylethyl) -N- (1-methylpropyl) amino or N- (1, 1-dimethylethyl) -N- (2-methylpropyl) amino;
Di- (Cι-C6-alkyl) amino: Di- (Cι-C4-alkyl) amino wie voranstehend genannt, sowie N,N-Dipentylamino, N,N-Dihexylamino, N-Methyl- N-pentylamino, N-Ethyl -N-pentylamino, N-Methyl -N-hexylamino oder N-Ethyl-N-hexylamino.Di- (-C 6 -alkyl) amino: di- (-C 4 -alkyl) amino as mentioned above, and N, N-dipentylamino, N, N-dihexylamino, N-methyl-N-pentylamino, N- Ethyl -N-pentylamino, N-methyl -N-hexylamino or N-ethyl-N-hexylamino.
Cι-C4~Alkylcarbonyl: z.B. Methylcarbonyl, Ethylcarbonyl , Propylcarbonyl, 1-Methylethylcarbonyl, Butylcarbonyl, 1-Methylpropylcarbonyl, 2-Methylpropylcarbonyl oder 1 , 1-Dimethylethylcarbonyl; Ci-Cβ-Alkylcarbonyl, sowie die Alkylcarbonylreste von Cι-C6-Alkylcarbonyl-Cι-C6-alkyl: Cι-C4-Alkylcarbonyl, wie voranstehend genannt, sowie z.B. Pentylcarbonyl, 1-Methyl - butylcarbonyl, 2-Methylbutylcarbonyl, 3-Methylbutylcarbonyl, 2,2-Dimethylpropylcarbonyl, 1-Ethylpropylcarbonyl, Hexyl- carbonyl , 1 , 1-Dimethylpropylcarbonyl , 1 , 2-Dimethylpropyl - carbonyl, 1-Methylpentylcarbonyl, 2-Methylpentylcarbonyl, 3-Methylpentylcarbonyl, 4-Methylpentylcarbonyl, 1, 1-Dimethyl- butylcarbonyl, 1, 2-Dimethylbutylcarbonyl, 1, 3-Dimethylbutyl - carbonyl, 2, 2, -Dimethylbutylcarbonyl, 2, 3-Dimethylbutyl - carbonyl, 3 , 3-Dimethylbutylcarbonyl, 1-Ethylbutylcarbonyl, 2-Ethylbutylcarbonyl, 1,1, 2-Trimethylpropylcarbonyl, 1,2, 2-Trimethylpropylcarbonyl , 1-Ethyl-l-methylpropylcarbonyl oder l-Ethyl-2-methylpropylcarbonyl ;C 1 -C 4 ~ alkylcarbonyl: for example methylcarbonyl, ethylcarbonyl, propylcarbonyl, 1-methylethylcarbonyl, butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl or 1, 1-dimethylethylcarbonyl; Ci-Cβ-alkylcarbonyl, and the alkylcarbonyl radicals of -CC 6 -alkylcarbonyl -CC-C 6 -alkyl: -C-C 4 -alkylcarbonyl, as mentioned above, and for example pentylcarbonyl, 1-methylbutylcarbonyl, 2-methylbutylcarbonyl, 3rd -Methylbutylcarbonyl, 2,2-dimethylpropylcarbonyl, 1-ethylpropylcarbonyl, hexylcarbonyl, 1, 1-dimethylpropylcarbonyl, 1, 2-dimethylpropylcarbonyl, 1-methylpentylcarbonyl, 2-methylpentylcarbonyl, 3-methylpentylcarbonyl, 4-methylpentylcarbonyl, 1 -Dimethylbutylcarbonyl, 1, 2-dimethylbutylcarbonyl, 1, 3-dimethylbutyl - carbonyl, 2, 2, -dimethylbutylcarbonyl, 2, 3-dimethylbutyl - carbonyl, 3, 3-dimethylbutylcarbonyl, 1-ethylbutylcarbonyl, 2-ethylbutylcarbonyl, 1, 1,2-trimethylpropylcarbonyl, 1,2,2-trimethylpropylcarbonyl, 1-ethyl-l-methylpropylcarbonyl or l-ethyl-2-methylpropylcarbonyl;
Cι-C2o-Alkylcarbonyl: Cχ-C6-Alkylcarbonyl, wie voranstehend genannt, sowie Heptylcarbonyl, Octylcarbonyl, Pentadecylcar- bonyl oder Heptadecylcarbonyl;C 1 -C 2 -alkylcarbonyl: Cχ-C 6 -alkylcarbonyl, as mentioned above, and heptylcarbonyl, octylcarbonyl, pentadecylcarbonyl or heptadecylcarbonyl;
- Cι-C6-Halogenalkylcarbonyl: einen Ci-Cg-Alkylcarbonylrest, wie vorstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder lod substituiert ist, also z.B. Chloracetyl, Dichloracetyl, Trichloracetyl, Fluoracetyl, Difluoracetyl, Trifluoracetyl, Chlorfluoracetyl, Dichlor- fluoracetyl, Chlordifluoracetyl, 2-Fluorethylcarbonyl,-C 1 -C 6 haloalkylcarbonyl: a Ci-Cg-alkylcarbonyl radical, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example chloroacetyl, dichloroacetyl, trichloroacetyl, fluoroacetyl, difluoroacetyl, trifluoroacetyl, Chlorofluoroacetyl, dichlorofluoroacetyl, chlorodifluoroacetyl, 2-fluoroethylcarbonyl,
2-Chlorethylcarbonyl, 2-Bromethylcarbonyl, 2-Iodethylcarbo- nyl, 2, 2-Difluorethylcarbonyl, 2, 2, 2-Trifluorethylcarbonyl, 2-Chlor-2-fluorethylcarbonyl, 2-Chlor-2, 2-difluorethylcarbonyl, 2, 2-Dichlor-2-fluorethylcarbonyl, 2,2, 2-Trichlorethyl- carbonyl, Pentafluorethylcarbonyl, 2-Fluorpropylcarbonyl, 3-Fluorpropylcarbonyl, 2 , 2-Difluorpropylcarbonyl, 2,3-Di- fluorpropylcarbonyl, 2-Chlorpropylcarbonyl, 3-Chlorpropylcar- bonyl, 2 , 3-Dichlorpropylcarbonyl, 2-Brompropylcarbonyl, 3-Brompropylcarbonyl, 3,3, 3-Trifluorpropylcarbonyl, 3 , 3 , 3-Trichlorpropylcarbonyl, 2, 2 , 3, 3, 3-Pentafluorpropylcarbonyl, Heptafluorpropylcarbonyl, 1- (Fluormethyl) -2-fluorethylcarbonyl, 1- (Chlormethyl) -2-chlorethylcarbonyl, 1- (Brommethyl) -2-bromethylcarbonyl, 4-Fluorbutylcarbonyl, 4-Chlor- butylcarbonyl, 4-Brombutylcarbonyl, Nonafluorbutylcarbonyl, 5-Fluorpentylcarbonyl, 5 -Chlorpentylcarbonyl, 5-Brompentyl- carbonyl, Perfluorpentylcarbonyl, 6-Fluorhexylcarbonyl, 6-Chlorhexylcarbonyl, 6 -Bromhexylcarbonyl oder Perfluorhexyl- carbonyl ;2-chloroethylcarbonyl, 2-bromoethylcarbonyl, 2-iodoethylcarbonyl, 2, 2-difluoroethylcarbonyl, 2, 2, 2-trifluoroethylcarbonyl, 2-chloro-2-fluoroethylcarbonyl, 2-chloro-2, 2-difluoroethylcarbonyl, 2, 2- Dichloro-2-fluoroethylcarbonyl, 2,2, 2-trichloroethylcarbonyl, pentafluoroethylcarbonyl, 2-fluoropropylcarbonyl, 3-fluoropropylcarbonyl, 2, 2-difluoropropylcarbonyl, 2,3-di-fluoropropylcarbonyl, 2-chloropropylcarbonyl, 3-chloropropylcarbonyl, 2, 3-dichloropropylcarbonyl, 2-bromopropylcarbonyl, 3-bromopropylcarbonyl, 3,3, 3-trifluoropropylcarbonyl, 3, 3, 3-trichloropropylcarbonyl, 2, 2, 3, 3, 3-pentafluoropropylcarbonyl, heptafluoropropylcarbonyl, 1- (fluoromethyl) - 2-fluoroethylcarbonyl, 1- (chloromethyl) -2-chloroethylcarbonyl, 1- (bromomethyl) -2-bromethylcarbonyl, 4-fluorobutylcarbonyl, 4-chlorobutylcarbonyl, 4-bromobutylcarbonyl, nonafluorobutylcarbonyl, 5-fluoropentylcarbonyl, 5-chloropentylcarbonyl, 5- Bromopentylcarbonyl, perfluoropentylcarbonyl, 6-fluorohexylcarbonyl, 6-chlorohexylcarbonyl, 6-bromhexylcar bonyl or perfluorohexylcarbonyl;
- Cι-C4~Alkoxycarbonyl, sowie die Alkoxycarbonylteile von- Cι-C 4 ~ alkoxycarbonyl, and the alkoxycarbonyl parts of
Di- (Cι-C4~alkyl) amino-Cι-C4-alkoxycarbonyl, also z.B. Methoxy- carbonyl, Ethoxycarbonyl, Propoxycarbonyl , 1-Methylethoxy- carbonyl, Butoxycarbonyl , 1-Methylpropoxycarbonyl, 2-Methyl- propoxycarbonyl oder 1, 1-Dimethylethoxycarbonyl;Di- (-C 4 ~ alkyl) amino -C -C 4 alkoxycarbonyl, that is, for example, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, 1-methylethoxy carbonyl, butoxycarbonyl, 1-methylpropoxycarbonyl, 2-methylpropoxycarbonyl or 1, 1-dimethylethoxycarbonyl;
(Ci-Cδ-Alkoxy) carbonyl; sowie die Alkoxycarbonylteile von Ci-Cε-Alkoxycarbonyloxy: (Cχ-C-Alkoxy) carbonyl, wie vorste¬ hend genannt, sowie z.B. Pentoxycarbonyl , 1-Methylbutoxycar- bonyl, 2-Methylbutoxycarbonyl , 3-Methylbutoxycarbonyl, 2,2-Dimethylpropoxycarbonyl, 1-Ethylpropoxycarbonyl, Hexoxy- carbonyl, 1, 1-Dimethylpropoxycarbonyl, 1, 2-Dimethylpropoxy- carbonyl, 1-Methylpentoxycarbonyl, 2-Methylpentoxycarbonyl, 3-Methylpentoxycarbonyl, 4-Methylpentoxycarbonyl, 1,1-Dime- thylbutoxycarbonyl , 1, 2-Dimethylbutoxycarbonyl , 1, 3-Dimethyl - butoxycarbonyl , 2 , 2-Dimethylbutoxycarbonyl , 2 , 3-Dimethylbut - oxycarbonyl, 3 , 3-Dimethylbutoxycarbonyl, 1-Ethylbutoxycarbo- nyl, 2-Ethylbutoxycarbonyl, 1, 1, 2-Trimethylpropoxycarbonyl, 1,2, 2-Trimethylpropoxycarbonyl , 1-Ethyl-l-methyl-propoxy- carbonyl oder l-Ethyl-2-methyl-propoxycarbonyl;(Ci-C δ alkoxy) carbonyl; and Alkoxycarbonylteile of Ci-Cε-alkoxycarbonyloxy (Cχ-C -alkoxy) carbonyl as mentioned vorste ¬ starting, as well as, for example, pentoxycarbonyl, 1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 2,2-dimethylpropoxycarbonyl, 1 -Ethylpropoxycarbonyl, hexoxycarbonyl, 1, 1-dimethylpropoxycarbonyl, 1, 2-dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1,1-dimethylbutoxycarbonyl, 1, 2-dimethylbutoxycarbonyl , 1, 3-dimethylbutoxycarbonyl, 2, 2-dimethylbutoxycarbonyl, 2, 3-dimethylbut - oxycarbonyl, 3, 3-dimethylbutoxycarbonyl, 1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl, 1, 1, 2-trimethylpropoxycarbonyl, 1,2 , 2-trimethylpropoxycarbonyl, 1-ethyl-l-methyl-propoxycarbonyl or l-ethyl-2-methyl-propoxycarbonyl;
Cι-C6-Halogenalkoxycarbonyl: einen Cι-C4-Alkoxycarbonylrest, wie voranstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder lod substituiert ist, also z.B. Fluormethoxycarbonyl, Difluormethoxycarbonyl , Trifluor- methoxycarbonyl , Chlordifluormethoxycarbonyl, Bromdifluormethoxycarbonyl , 2-Fluorethoxycarbonyl, 2-Chlorethoxycar- bonyl, 2-Bromethoxycarbonyl, 2-Iodethoxycarbonyl, 2,2-Di- fluorethoxycarbonyl, 2, 2, 2-Trifluorethoxycarbonyl, 2-Chlor- 2-fluorethoxycarbonyl , 2-Chlor-2 , 2-difluorethoxycarbonyl , 2 , 2-Dichlor-2-fluorethoxycarbonyl, 2,2, 2-Trichlorethoxycar- bonyl, Pentafluorethoxycarbonyl, 2-Fluorpropoxycarbonyl, 3-Fluorpropoxycarbonyl, 2-Chlorpropoxycarbonyl , 3-Chlorpropo- xycarbonyl , 2-Brompropoxycarbonyl , 3-Brompropoxycarbonyl , 2 , 2-Difluorpropoxycarbonyl, 2, 3-Difluorpropoxycarbonyl, 2 , 3-Dichlorpropoxycarbonyl , 3,3, 3-Trifluorpropoxycarbonyl , 3,3, 3-Trichlorpropoxycarbonyl, 2,2,3,3, 3-Pentafluorpropoxy- carbonyl, Heptafluorpropoxycarbonyl, 1- (Fluormethyl) -2-fluorethoxycarbonyl , 1- (Chlormethyl) -2-chlorethoxycarbonyl, 1- (Brommethyl) -2-bromethoxycarbonyl, 4-Fluorbutoxycarbonyl, 4-Chlorbutoxycarbonyl, 4-Brombutoxycarbonyl, 4-Iodbutoxy- carbonyl, 5-Fluorpentoxycarbonyl, 5-Chlorpentoxycarbonyl, 5-Brompentoxycarbonyl, 6-Fluorhexoxycarbonyl, 6-Chlorhexoxy- carbonyl oder 6 -Bromhexoxycarbonyl;C 1 -C 6 -haloalkoxycarbonyl: a C 1 -C 4 -alkoxycarbonyl radical, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example fluoromethoxycarbonyl, difluoromethoxycarbonyl, trifluoromethoxycarbonyl, chlorodifluoromethoxycarbonyl, bromodifluoromethoxy 2-fluoroethoxycarbonyl, 2-chloroethoxycarbonyl, 2-bromoethoxycarbonyl, 2-iodoethoxycarbonyl, 2,2-di-fluoroethoxycarbonyl, 2, 2, 2-trifluoroethoxycarbonyl, 2-chloro-2-fluoroethoxycarbonyl, 2-chloro-2, 2- difluoroethoxycarbonyl, 2, 2-dichloro-2-fluoroethoxycarbonyl, 2,2, 2-trichloroethoxycarbonyl, pentafluoroethoxycarbonyl, 2-fluoropropoxycarbonyl, 3-fluoropropoxycarbonyl, 2-chloropropoxycarbonyl, 3-chloropropoxycarbonyl, 2-bromopropoxycarbonyl, 3-bromopropoxycarbonyl 2,2-difluoropropoxycarbonyl, 2,3-difluoropropoxycarbonyl, 2,3-dichloropropoxycarbonyl, 3,3,3-trifluoropropoxycarbonyl, 3,3,3-trichloropropoxycarbonyl, 2,2,3,3, 3-pentafluoropropoxycarbonyl, heptafluoropropoxy carbonyl, 1- (fluoromethyl) -2-fluoroethoxycarbonyl, 1- (chloromethyl) -2-chloroethoxycarbonyl, 1- (bromomethyl) -2-bromethoxycarbonyl, 4-fluorobutoxycarbonyl, 4-chlorobutoxycarbonyl, 4-bromobutoxycarbonyl, 4-iodobutoxycarbonyl, 5-fluoropentoxycarbonyl, 5-chloropentoxycarbonyl, 5-bromopentoxycarbonyl, 6-fluorohexoxycarbonyl, 6-chlorohexoxycarbonyl or 6-bromhexoxycarbonyl;
(Cι-C4-Alkylamino) carbonyl: z.B. Methylaminocarbonyl, Ethyl - aminocarbonyl , Propylaminocarbonyl, 1-Methylethylaminocarbo- nyl, Butylaminocarbonyl, 1-Methylpropylaminocarbonyl, 2-Methylpropylaminocarbonyl oder 1, 1-Dimethylethylamino- carbonyl ;(C 1 -C 4 -alkylamino) carbonyl: for example methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl, 1-methylethylaminocarbonyl, butylaminocarbonyl, 1-methylpropylaminocarbonyl, 2-methylpropylaminocarbonyl or 1, 1-dimethylethylaminocarbonyl;
(Ci-Cδ-Alkylamino) carbonyl : (Cι-C4-Alkylamino) carbonyl , wie vorstehend genannt, sowie z.B. Pentylaminocarbonyl, 1-Methyl' butylaminocarbonyl, 2-Methylbutylaminocarbonyl, 3-Methyl- butylaminocarbonyl, 2 , 2-Dimethylpropylaminocarbonyl, 1-Ethyl propylaminocarbonyl, Hexylaminocarbonyl , 1, 1-Dimethylpropyl- aminocarbonyl , 1, 2-Dimethylpropylaminocarbonyl, 1-Methylpen- tylaminocarbonyl, 2-Methylpentylaminocarbonyl, 3-Methyl- pentylaminocarbonyl, 4-Methylpentylaminocarbonyl, 1,1-Di- methylbutylaminocarbonyl, 1, 2-Dimethylbutylaminocarbonyl, 1, 3-Dimethylbutylaminocarbonyl, 2, 2-Dimethylbutylaminocarbonyl, 2, 3-Dimethylbutylaminocarbonyl, 3 , 3-Dimethylbutyl - aminocarbonyl , 1-Ethylbutylaminocarbonyl, 2-Ethylbutylaminocarbonyl, 1, 1, 2-Trimethylpropylaminocarbonyl, 1,2,2-Tri- methylpropylaminocarbonyl, 1-Ethyl-l-methylpropylamino- carbonyl oder l-Ethyl-2-methylpropylaminocarbonyl;(Ci-C δ- alkylamino) carbonyl: (-C-C 4 -alkylamino) carbonyl, as mentioned above, and for example pentylaminocarbonyl, 1-methyl'-butylaminocarbonyl, 2-methylbutylaminocarbonyl, 3-methylbutylaminocarbonyl, 2, 2-dimethylpropylaminocarbonyl, 1-ethyl propylaminocarbonyl, hexylaminocarbonyl, 1, 1-dimethylpropylaminocarbonyl, 1, 2-dimethylpropylaminocarbonyl, 1-methylpentylaminocarbonyl, 2-methylpentylaminocarbonyl, 3-methylpentylaminocarbonyl, 4-methylpentylaminocarbonyl, 1,1-dimethyl , 2-Dimethylbutylaminocarbonyl, 1, 3-Dimethylbutylaminocarbonyl, 2, 2-Dimethylbutylaminocarbonyl, 2, 3-Dimethylbutylaminocarbonyl, 3, 3-Dimethylbutyl - aminocarbonyl, 1-Ethylbutylaminocarbonyl, 2-Ethylbutylaminylcarbonyl, 1, 1 , 2-trimethylpropylaminocarbonyl, 1-ethyl-1-methylpropylaminocarbonyl or 1-ethyl-2-methylpropylaminocarbonyl;
Di- (Cχ-C4-alkyl) -aminocarbonyl : z.B. N,N-Dimethylaminocarbo- nyl, N,N-Diethylaminocarbonyl, N, N-Di- (1-methylethyl) aminocarbonyl, N,N-Dipropylaminocarbonyl, N,N-Dibutylaminocarbo- nyl, N, N-Di- (1-methylpropyl) -aminocarbonyl, N, N-Di- (2-methyl- propyl) -aminocarbonyl, N,N-Di- (1, 1-dimethylethyl) -aminocarbo- nyl, N-Ethyl-N-methylaminocarbonyl, N-Methyl-N-propylamino- carbonyl, N-Methyl-N- (1-methylethyl) -aminocarbonyl, N-Butyl- N-methylaminocarbonyl , N-Methyl-N- (1-methylpropyl) -amino- carbonyl, N-Methyl-N- (2-methylpropyl) -aminocarbonyl, N- (1 , 1-Dimethylethyl) -N-methylaminocarbonyl, N-Ethyl-N-pro- pylaminocarbonyl, N-Ethyl-N- (1-methylethyl) -aminocarbonyl, N-Butyl-N-ethylaminocarbonyl, N-Ethyl-N- (1-methylpropyl) - aminocarbonyl, N-Ethyl-N- (2-methylpropyl) -aminocarbonyl, N-Ethyl-N- (1, 1-dimethylethyl) -aminocarbonyl, N- (1-Methyl- ethyl) -N-propylaminocarbonyl, N-Butyl-N-propylaminocarbonyl, N- (1-Methylpropyl) -N-propylaminocarbonyl, N-(2-Methyl- propyl) -N-propylaminocarbonyl , N- (1 , 1-Dimethylethyl) -N-pro- pylaminocarbonyl , N-Butyl-N- (1-methylethyl) -aminocarbonyl , N- (1-Methylethyl) -N- (1-methylpropyl) -aminocarbonyl, N- (1-Methylethyl) -N- (2-methylpropyl) -aminocarbonyl, N- (1, 1-Dimethylethyl) -N- (1-methylethyl) -aminocarbonyl, N-Butyl-N- (1-methylpropyl) -aminocarbonyl, N-Butyl-N- (2-methyl - propyl) -aminocarbonyl, N-Butyl-N- (1 , 1-dimethylethyl) -amino- carbonyl, N- (1-Methylpropyl) -N- (2-methylpropyl) -aminocarbonyl , N- (1 , 1-Dimethylethyl) -N- (1-methylpropyl) -amino- carbonyl oder N- (1, 1-Dimethylethyl) -N- (2-methylpropyl) -aminocarbonyl ; Cι-C6-Alkoxy-Cι-C6-alkyl: durch Cι-C6-Alkoxy, wie vorstehend genannt, substituiertes Ci-Cβ-Alkyl, also z.B. für Methoxy- methyl, Ethoxymethyl , Propoxymethyl , (1-Methylethoxy) methyl, Butoxymethyl , (1-Methylpropoxy) methyl, (2-Methylpropoxy) - methyl, (1, 1-Dimethylethoxy) methyl, 2- (Methoxy) ethyl,Di- (Cχ-C 4 -alkyl) -aminocarbonyl: for example N, N-dimethylaminocarbonyl, N, N-diethylaminocarbonyl, N, N-di- (1-methylethyl) aminocarbonyl, N, N-dipropylaminocarbonyl, N, N -Dibutylaminocarbonyl, N, N-di- (1-methylpropyl) -aminocarbonyl, N, N-di- (2-methylpropyl) -aminocarbonyl, N, N-di- (1, 1-dimethylethyl) -aminocarbo - nyl, N-ethyl-N-methylaminocarbonyl, N-methyl-N-propylamino-carbonyl, N-methyl-N- (1-methylethyl) -aminocarbonyl, N-butyl-N-methylaminocarbonyl, N-methyl-N- ( 1-methylpropyl) aminocarbonyl, N-methyl-N- (2-methylpropyl) aminocarbonyl, N- (1, 1-dimethylethyl) -N-methylaminocarbonyl, N-ethyl-N-propylaminocarbonyl, N-ethyl -N- (1-methylethyl) aminocarbonyl, N-butyl-N-ethylaminocarbonyl, N-ethyl-N- (1-methylpropyl) aminocarbonyl, N-ethyl-N- (2-methylpropyl) aminocarbonyl, N-ethyl -N- (1, 1-dimethylethyl) aminocarbonyl, N- (1-methylethyl) -N-propylaminocarbonyl, N-butyl-N-propylaminocarbonyl, N- (1-methylpropyl) -N-propylaminocarbonyl, N- ( 2-methyl-propyl) -N-propyl aminocarbonyl, N- (1, 1-dimethylethyl) -N-propylaminocarbonyl, N-butyl-N- (1-methylethyl) -aminocarbonyl, N- (1-methylethyl) -N- (1-methylpropyl) aminocarbonyl, N- (1-methylethyl) -N- (2-methylpropyl) aminocarbonyl, N- (1, 1-dimethylethyl) -N- (1-methylethyl) aminocarbonyl, N-butyl-N- (1-methylpropyl) - aminocarbonyl, N-butyl-N- (2-methyl-propyl) -aminocarbonyl, N-butyl-N- (1, 1-dimethylethyl) -amino-carbonyl, N- (1-methylpropyl) -N- (2-methylpropyl ) aminocarbonyl, N- (1, 1-dimethylethyl) -N- (1-methylpropyl) aminocarbonyl or N- (1, 1-dimethylethyl) -N- (2-methylpropyl) aminocarbonyl; C 1 -C 6 -alkoxy-C 6 -C 6 -alkyl: C 1 -C 6 -alkoxy, as mentioned above, substituted C 1 -C 6 -alkyl, for example for methoxymethyl, ethoxymethyl, propoxymethyl, (1-methylethoxy) methyl , Butoxymethyl, (1-methylpropoxy) methyl, (2-methylpropoxy) methyl, (1, 1-dimethylethoxy) methyl, 2- (methoxy) ethyl,
2- (Ethoxy) ethyl, 2- (Propoxy) ethyl, 2- (1-Methylethoxy) ethyl, 2- (Butoxy) ethyl, 2- (1-Methylpropoxy) ethyl, 2-(2-Methyl- propoxy) ethyl , 2- (1, 1-Dirnethylethoxy) ethyl, 2- (Methoxy) - propyl, 2- (Ethoxy) propyl, 2- (Propoxy) propyl, 2-(l-Methyl- ethoxy) -propyl, 2- (Butoxy) propyl, 2- (1-Methylpropoxy) propyl, 2- (2-Methylpropoxy) propyl, 2- (1, 1-Dimethylethoxy) propyl, 3- (Methoxy) propyl , 3- (Ethoxy) -propyl , 3- (Propoxy) propyl , 3- (1-Methylethoxy) propyl, 3- (Butoxy) propyl, 3-(l-Methyl- propoxy) propyl, 3- (2-Methylpropoxy) propyl, 3- (1, 1-Dirnethyl - ethoxy) propyl, 2- (Methoxy) butyl, 2- (Ethoxy) butyl, 2- (Propoxy) butyl, 2- (1-Methylethoxy) butyl, 2- (Butoxy) butyl, 2- (1-Methylpropoxy) butyl, 2- (2-Methylpropoxy) butyl, 2- (1, 1-Dimethylethoxy) butyl, 3- (Methoxy) butyl, 3-(Ethoxy)- butyl, 3- (Propoxy) butyl, 3- (1-Methylethoxy) butyl, 3- (Butoxy) - butyl, 3- (1-Methylpropoxy) butyl , 3- (2-Methylpropoxy) butyl, 3- (1, 1-Dirnethylethoxy) butyl, 4- (Methoxy) butyl, 4- (Ethoxy) - butyl, 4- (Propoxy) butyl, 4- (1-Methylethoxy) butyl, 4- (Butoxy) - butyl, 4- (1-Methylpropoxy) butyl, 4- (2-Methylpropoxy) butyl 4- (1, 1-Dimethylethoxy) butyl, 5-Methoxypentyl, 5 -Ethoxypentyl, 6 -Methoxyhexyl oder 6-Ethoxyhexyl;2- (ethoxy) ethyl, 2- (propoxy) ethyl, 2- (1-methylethoxy) ethyl, 2- (butoxy) ethyl, 2- (1-methylpropoxy) ethyl, 2- (2-methylprooxy) ethyl, 2- (1, 1-dimethylethoxy) ethyl, 2- (methoxy) propyl, 2- (ethoxy) propyl, 2- (propoxy) propyl, 2- (l-methylethoxy) propyl, 2- (butoxy) propyl, 2- (1-methylpropoxy) propyl, 2- (2-methylpropoxy) propyl, 2- (1, 1-dimethylethoxy) propyl, 3- (methoxy) propyl, 3- (ethoxy) propyl, 3- (propoxy ) propyl, 3- (1-methylethoxy) propyl, 3- (butoxy) propyl, 3- (l-methylpropoxy) propyl, 3- (2-methylpropoxy) propyl, 3- (1, 1-dirnethylethoxy) propyl, 2- (methoxy) butyl, 2- (ethoxy) butyl, 2- (propoxy) butyl, 2- (1-methylethoxy) butyl, 2- (butoxy) butyl, 2- (1-methylpropoxy) butyl, 2- (2-methylpropoxy) butyl, 2- (1, 1-dimethylethoxy) butyl, 3- (methoxy) butyl, 3- (ethoxy) butyl, 3- (propoxy) butyl, 3- (1-methylethoxy) butyl, 3 - (Butoxy) - butyl, 3- (1-methylpropoxy) butyl, 3- (2-methylpropoxy) butyl, 3- (1, 1-dimethylethyloxy) butyl, 4- (methoxy) butyl, 4- (ethoxy) butyl, 4- (propoxy) butyl, 4- (1-methylethoxy) butyl, 4- (butoxy) butyl, 4- (1-methylpropoxy) butyl, 4- (2-methylpropoxy) butyl 4 - (1, 1-dimethylethoxy) butyl, 5-methoxypentyl, 5-ethoxypentyl, 6-methoxyhexyl or 6-ethoxyhexyl;
Cι-C4-Alkoxy-Cι-C4-alkoxy-Rest von Cι-C4-Alkoxy-Cι-C4-alkoxy- carbonyl : durch Cι-C4-Alkoxy, wie vorstehend genannt, substituiertes Cι~C4-Alkoxy, also z.B. für Methoxymethoxy, Ethoxy- methoxy, Propoxymethoxy, (1-Methylethoxy) methoxy, Butoxy- methoxy, (1-Methylpropoxy)methoxy, (2-Methylpropoxy)methoxy, (1, 1-Dimethylethoxy) methoxy, 2- (Methoxy) ethoxy, 2- (Ethoxy) - ethoxy, 2- (Propoxy) ethoxy, 2- (1-Methylethoxy) ethoxy, 2- (Butoxy) ethoxy, 2- (1-Methylpropoxy) ethoxy, 2-(2-Methyl- propoxy) ethoxy, 2- (1, 1-Dimethylethoxy) ethoxy, 2- (Methoxy) - propoxy, 2- (Ethoxy) propoxy, 2- (Propoxy) propoxy, 2-(l-Methyl- ethoxy) propoxy, 2- (Butoxy) -propoxy, 2- (1-Methylpropoxy) propoxy, 2- (2-Methylpropoxy) -propoxy, 2- (1, 1-Dimethylethoxy) - propoxy, 3- (Methoxy) -propoxy, 3- (Ethoxy) propoxy, 3- (Propoxy) - propoxy, 3- (1-Methylethoxy) -propoxy, 3- (Butoxy)propoxy, 3- (1-Methylpropoxy) -propoxy, 3- (2-Methylpropoxy) propoxy, 3- (1, 1-Dirnethylethoxy) propoxy, 2- (Methoxy) butoxy, 2- (Ethoxy) butoxy, 2- (Propoxy) butoxy, 2- (1-Methylethoxy) butoxy, 2- (Butoxy) -butoxy, 2- (1-Methylpropoxy) butoxy, 2-(2-Methyl- propoxy)butoxy, 2- (1, 1-Dirnethylethoxy)butoxy, 3- (Methoxy) butoxy, 3- (Ethoxy) -butoxy, 3- (Propoxy) butoxy, 3-(l-Me- thylethoxy) butoxy, 3- (Butoxy) -butoxy, 3- (1-Methylprop- oxy)butoxy, 3- (2-Methylpropoxy) butoxy, 3- (1, 1-Dimethyl - ethoxy) butoxy, 4- (Methoxy) -butoxy, 4- (Ethoxy) -butoxy, 4- (Propoxy) butoxy, 4- (1-Methylethoxy) butoxy, 4- (Butoxy) butoxy, 4- (1-Methylpropoxy) butoxy, 4- (2-Methylpropoxy) butoxy oder 4- (1, 1-Dimethylethoxy) butoxy;C 1 -C 4 -alkoxy-C 4 -alkoxy radical of C 1 -C 4 -alkoxy-C 4 -alkoxy-carbonyl: C 1 -C 4 -alkoxy, as mentioned above, substituted C 1 -C 4 - Alkoxy, e.g. for methoxymethoxy, ethoxy-methoxy, propoxymethoxy, (1-methylethoxy) methoxy, butoxy-methoxy, (1-methylpropoxy) methoxy, (2-methylpropoxy) methoxy, (1, 1-dimethylethoxy) methoxy, 2- ( Methoxy) ethoxy, 2- (ethoxy) ethoxy, 2- (propoxy) ethoxy, 2- (1-methylethoxy) ethoxy, 2- (butoxy) ethoxy, 2- (1-methylpropoxy) ethoxy, 2- (2-methyl - propoxy) ethoxy, 2- (1, 1-dimethylethoxy) ethoxy, 2- (methoxy) propoxy, 2- (ethoxy) propoxy, 2- (propoxy) propoxy, 2- (l-methylethoxy) propoxy, 2 - (Butoxy) propoxy, 2- (1-methylpropoxy) propoxy, 2- (2-methylpropoxy) propoxy, 2- (1, 1-dimethylethoxy) propoxy, 3- (methoxy) propoxy, 3- (ethoxy ) propoxy, 3- (propoxy) propoxy, 3- (1-methylethoxy) propoxy, 3- (butoxy) propoxy, 3- (1-methylpropoxy) propoxy, 3- (2-methylpropoxy) propoxy, 3- ( 1, 1-Dirnethylethoxy) propoxy, 2- (methoxy) b utoxy, 2- (ethoxy) butoxy, 2- (propoxy) butoxy, 2- (1-methylethoxy) butoxy, 2- (butoxy) butoxy, 2- (1-methylpropoxy) butoxy, 2- (2-methylprooxy) ) butoxy, 2- (1, 1-dimethylethoxy) butoxy, 3- (methoxy) butoxy, 3- (ethoxy) butoxy, 3- (propoxy) butoxy, 3- (l-methylethoxy) butoxy, 3- ( Butoxy) butoxy, 3- (1-methylprop- oxy) butoxy, 3- (2-methylpropoxy) butoxy, 3- (1, 1-dimethylethoxy) butoxy, 4- (methoxy) butoxy, 4- (ethoxy) butoxy, 4- (propoxy) butoxy, 4 - (1-methylethoxy) butoxy, 4- (butoxy) butoxy, 4- (1-methylpropoxy) butoxy, 4- (2-methylpropoxy) butoxy or 4- (1, 1-dimethylethoxy) butoxy;
C3-C6-Alkenyl, sowie die Alkenylteile von C3-C6-Alkenyl- carbonyl, C3 -C6-Alkenyloxy, C3-C6-Alkenylthio, N-(C3-C6-Alkenyl) -N- (Cι-C6) alkylamino und Di (C3 -C6-alke- nyl) amino: z.B. Prop-2-en-l-yl, But-l-en-4-yl, 1-Methyl- prop-2-en-l-yl, 2-Methyl-prop-2-en-l-yl, 2-Buten-l-yl, l-Penten-3-yl, l-Penten-4-yl, 2-Penten-4-yl, 1-Methyl- but-2-en-l-yl, 2-Methyl-but-2-en-l-yl, 3-Methyl- but-2-en-l-yl, l-Methyl-but-3-en-l-yl, 2-Methyl- but-3-en-l-yl, 3-Methyl-but-3-en-l-yl, 1, 1-Dimethyl- prop-2-en-l-yl, 1, 2-Dimethyl-prop-2-en-l-yl, 1-Ethyl- prop-2-en-l-yl, Hex-3-en-l-yl, Hex-4-en-l-yl, Hex-5-en-l-yl, l-Methyl-pent-3-en-l-yl, 2-Methyl-pent-3-en-l-yl, 3-Methyl- pent-3-en-l-yl, 4-Methyl-pent-3-en-l-yl, 1-Methyl- pent-4-en-l-yl, 2-Methyl-pent-4-en-l-yl, 3-Methyl- pent-4-en-l-yl, 4-Methyl-pent-4-en-l-yl, 1, 1-Dimethyl- but-2-en-l-yl, 1, l-Dimethyl-but-3-en-l-yl , 1, 2-Dimethyl- but-2-en-l-yl, 1, 2-Dimethyl-but-3-en-l-yl, 1, 3-Dimethyl- but-2-en-l-yl, 1, 3-Dimethyl-but-3-en-l-yl, 2 , 2-Dimethyl- but-3-en-l-yl, 2 , 3-Dimethyl-but-2-en-l-yl , 2, 3-Dimethyl- but-3-en-l-yl, 3, 3-Dimethyl-but-2-en-l-yl, l-Ethyl-but-2- en-l-yl, l-Ethyl-but-3-en-l-yl, 2-Ethyl-but-2-en-l-yl, 2-Ethyl-but-3-en-l-yl, 1, 1, 2-Trimethyl-prop-2-en-l-yl, l-Ethyl-l-methyl-prop-2-en-l-yl oder l-Ethyl-2-methyl- prop-2-en-l-yl;C 3 -C 6 alkenyl, and the alkenyl parts of C 3 -C 6 alkenyl carbonyl, C 3 -C 6 alkenyloxy, C 3 -C 6 alkenylthio, N- (C 3 -C 6 alkenyl) - N- (-C-C 6 ) alkylamino and di (C 3 -C 6 -alkenyl) amino: for example prop-2-en-1-yl, but-1-en-4-yl, 1-methyl-prop -2-en-l-yl, 2-methyl-prop-2-en-l-yl, 2-butene-l-yl, l-penten-3-yl, l-penten-4-yl, 2-pentene -4-yl, 1-methyl-but-2-en-l-yl, 2-methyl-but-2-en-l-yl, 3-methyl-but-2-en-l-yl, l-methyl -but-3-en-l-yl, 2-methyl-but-3-en-l-yl, 3-methyl-but-3-en-l-yl, 1, 1-dimethylprop-2-ene -l-yl, 1,2-dimethyl-prop-2-en-l-yl, 1-ethyl-prop-2-en-l-yl, hex-3-en-l-yl, hex-4-ene -l-yl, hex-5-en-l-yl, l-methyl-pent-3-en-l-yl, 2-methyl-pent-3-en-l-yl, 3-methyl-pent-3 -en-1-yl, 4-methyl-pent-3-en-1-yl, 1-methyl-pent-4-en-1-yl, 2-methyl-pent-4-en-1-yl, 3 -Methyl-pent-4-en-1-yl, 4-methyl-pent-4-en-1-yl, 1, 1-dimethyl-but-2-en-1-yl, 1, 1-dimethyl-but -3-en-1-yl, 1, 2-dimethyl-but-2-en-1-yl, 1, 2-dimethyl-but-3-en-1-yl, 1, 3-dimethyl-but-2 -en-l-yl, 1,3-dimethylbut-3-ene -l-yl, 2,2-dimethyl-but-3-en-l-yl, 2,3-dimethyl-but-2-en-l-yl, 2,3-dimethyl-but-3-en-l -yl, 3,3-dimethyl-but-2-en-1-yl, 1-ethyl-but-2-en-1-yl, 1-ethyl-but-3-en-1-yl, 2-ethyl -but-2-en-l-yl, 2-ethyl-but-3-en-l-yl, 1, 1, 2-trimethyl-prop-2-en-l-yl, l-ethyl-l-methyl -prop-2-en-l-yl or l-ethyl-2-methyl-prop-2-en-l-yl;
C2-C6-Alkenyl, sowie die Alkenylteile von C2-Cδ-Alkenyl- carbonyl : C3-C6-Alkenyl, wie voranstehend genannt, sowie Ethenyl;C 2 -C 6 alkenyl, and the alkenyl parts of C 2 -C δ alkenyl carbonyl: C 3 -C 6 alkenyl, as mentioned above, and ethenyl;
C3-C6-Halogenalkenyl : einen C3-Cg-Alkenylrest, wie vorstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder lod substituiert ist, also z.B. 2-Chlorallyl, 3-Chlorallyl, 2 , 3-Dichlorallyl, 3 , 3-Dichlorallyl, 2,3,3-Tri- chlorallyl, 2, 3-Dichlorbut-2-enyl, 2-Bromallyl, 3-Bromallyl, 2, 3-Dibromallyl, 3 , 3-Dibromallyl, 2, 3, 3-Tribromallyl oder 2, 3-Dibrombut-2-enyl;C 3 -C 6 haloalkenyl: a C 3 -Cg alkenyl radical, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example 2-chloroallyl, 3-chloroallyl, 2, 3 -Dichlorallyl, 3, 3-dichlorallyl, 2,3,3-trichlorallyl, 2,3-dichlorobut-2-enyl, 2-bromoallyl, 3-bromoallyl, 2, 3-dibromoallyl, 3, 3-dibromoallyl, 2 , 3, 3-tribromoallyl or 2,3-dibromobut-2-enyl;
C3-C6-Alkinyl, sowie die Alkinylteile von C3-C6-Alkinyl- carbonyl, C3-C6-Alkinyloxy, C3-C6-Alkinylthio, N-(C3-C6-A1- kinyl) -N- (Ci-Cδ-alkyl) -amino und Di (C3-C6-alkinyl) amino: z.B. Propargyl, But-l-in-3-yl, But-l-in-4-yl, But-2-in-l-yl, Pent-l-in-3-yl , Pent-l-in-4-yl , Pent-l-in-5-yl , Pent-2-in-l- yl , Pent-2-in-4-yl , Pent-2-in-5-yl , 3-Methyl-but-l-in-3-yl , 3-Methyl-but-l-in-4-yl , Hex-l-in-3-yl , Hex-l-in-4-yl , Hex-l-in-5-yl , Hex-l-in-6-yl , Hex-2-in-l-yl , Hex-2-in-4-yl , Hex-2-in-5-yl , Hex-2-in-6-yl , Hex-3-in-l-yl , Hex-3-in-2-yl ,C 3 -C 6 alkynyl, and the alkynyl parts of C 3 -C 6 alkynylcarbonyl, C 3 -C 6 alkynyloxy, C 3 -C 6 alkynylthio, N- (C 3 -C 6 -A1- kynyl ) -N- (Ci-C δ- alkyl) -amino and di (C 3 -C 6 -alkynyl) amino: for example propargyl, but-l-in-3-yl, but-l-in-4-yl, But-2-in-l-yl, Pent-1-in-3-yl, Pent-1-in-4-yl, Pent-1-in-5-yl, Pent-2-in-1-yl, Pent-2-in-4-yl, Pent-2-in-5-yl, 3-methyl-but-l-in-3-yl, 3-methyl-but-l-in-4-yl, hex-l-in-3-yl, hex l-in-4-yl, hex-l-in-5-yl, hex-l-in-6-yl, hex-2-in-l-yl, hex-2-in-4-yl, hex 2-in-5-yl, hex-2-in-6-yl, hex-3-in-l-yl, hex-3-in-2-yl,
3-Methyl-pent-l-in-3-yl , 3-Methyl-pent-l-in-4-yl , 3-Methyl- pent-l-in-5-yl , 4-Methyl-pent-2-in-4-yl oder 4-Methyl- pent-2-in-5-yl ;3-methyl-pent-l-in-3-yl, 3-methyl-pent-l-in-4-yl, 3-methyl-pent-l-in-5-yl, 4-methyl-pent-2- in-4-yl or 4-methylpent-2-in-5-yl;
C2-C6-Alkinyl, sowie die Alkinylteile von C2-C6-Alkinyl- carbonyl : C3-C6-Alkinyl, wie voranstehend genannt, sowie Ethinyl ;C 2 -C 6 alkynyl, and the alkynyl parts of C 2 -C 6 alkynylcarbonyl: C 3 -C 6 alkynyl, as mentioned above, and ethynyl;
C3-C6-Halogenalkinyl : einen C3-C6-Alkinylrest, wie vorstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder lod substituiert ist, also z.B. 1,1-Difluor- prop-2-in-l-yl, 3-Iod-prop-2-in-l-yl, 4-Fluorbut-2-in-l-yl, 4-Chlorbut-2-in-l-yl, 1, 1-Difluorbut-2-in-l-yl, 4-Iod- but-3-in-l-yl, 5-Fluorpent-3-in-l-yl, 5-Iod-pent-4-in-l-yl, 6-Fluor-hex-4-in-l-yl oder 6-Iod-hex-5-in-l-yl ;C 3 -C 6 haloalkynyl: a C 3 -C 6 alkynyl radical, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example 1,1-difluoroprop-2- in-l-yl, 3-iodo-prop-2-in-l-yl, 4-fluorobut-2-in-l-yl, 4-chlorobut-2-in-l-yl, 1, 1-difluorobut- 2-in-l-yl, 4-iodobut-3-in-l-yl, 5-fluoropent-3-in-l-yl, 5-iodo-pent-4-in-l-yl, 6- Fluoro-hex-4-in-1-yl or 6-iodo-hex-5-in-1-yl;
C3-C6~Cycloalkyl, sowie die Cycloalkylteile von C3-C6-Cyclo- alkylcarbonyl : z.B. Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl;C 3 -C 6 ~ cycloalkyl, and the cycloalkyl parts of C 3 -C 6 cycloalkylcarbonyl: for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;
C3-C6-Halogencycloalkyl : einen C3-C6-Cycloalkylrest, wie voranstehend, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder lod substituiert ist, also z.B. 2 , 2-Dichlorcy- cloprop-1-yl, 2, 2-Difluorcycloprop- 1-yl, 3 -Chlorcyclo- pent-1-yl, 3 -Fluorcyclopent-1-yl, 3 -Bromcyclopent-1-yl, 3 , 3 -Dichlorcyclopent-1-yl, 3 , 3 -Difluorcyclopent- 1-yl, 4 -Chlorcyclohex-1-yl, 4 -Fluorcyclohex-1-yl, 4-Bromcyclo- hex-l-yl, 4 , 4 -Dichlorcyclohex- 1-yl oder 4, 4 -Difluorcyclo- hex-l-yl;C 3 -C 6 halocycloalkyl: a C 3 -C 6 cycloalkyl radical, as above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example 2,2-dichlorocycloprop-1-yl , 2, 2-difluorocycloprop-1-yl, 3 -chlorocyclopent-1-yl, 3-fluorocyclopent-1-yl, 3-bromocyclopent-1-yl, 3, 3 -dichlorocyclopent-1-yl, 3, 3 -Difluorocyclopent-1-yl, 4 -chlorocyclohex-1-yl, 4 -fluorocyclohex-1-yl, 4-bromocyclohex-1-yl, 4, 4 -dichlorocyclohex-1-yl or 4, 4 -difluorocyclo-hex -l-yl;
Heterocyclyl, sowie Heterocyclylteile von Heterocyclylcarbo- nyl, Heterocyclyl-Ci-Cε-alkyl, Heterocyclyloxy, Heterocyclyl - aminocarbonyl: ein gesättigter, partiell gesättigter oder un- gesättiger 5- oder 6-gliedriger, C-gebundener, hetero- cyclischer Ring, der ein bis vier gleiche oder verschiedene Heteroatome, ausgewählt aus folgender Gruppe: Sauerstoff, Schwefel oder Stickstoff, enthält, also z.B. 5-gliedrige Ringe wie:Heterocyclyl, and also heterocyclyl parts of heterocyclylcarbonyl, heterocyclyl-Ci-Cε-alkyl, heterocyclyloxy, heterocyclyl - aminocarbonyl: a saturated, partially saturated or unsaturated 5- or 6-membered, C-linked, heterocyclic ring, the one up to four identical or different heteroatoms, selected from the following group: contains oxygen, sulfur or nitrogen, for example 5-link rings such as:
Tetrahydrofuran-2-yl, Tetrahydrofuran-3-yl, Tetrahydrothien- 2-yl, Tetrahydrothien-3-yl,Tetrahydropyrrol-2-yl, Tetrahydro- pyrrol-3-yl, 2, 3-Dihydrofuran-2-yl, 2, 3-Dihydrofuran-3-yl, 2,5-Dihydrofuran-2-yl, 2, 5-Dihydrofuran-3-yl, 4,5-Dihydro- furan-2-yl, 4, 5-Dihydrofuran-3-yl, 2, 3-Dihydrothien-2-yl, 2,3-Dihydrothien-3-yl, 2, 5-Dihydrothien-2-yl, 2,5-Dihydro- thien-3-yl, 4 , 5-Dihydrothien-2-yl, 4, 5-Dihydrothien-3-yl, 2,3-Dihydro-lH-pyrrol-2-yl, 2 , 3-Dihydro-lH-pyrrol-3-yl, 2 , 5-Dihydro-lH-pyrrol-2-yl , 2 , 5-Dihydro-lH-pyrrol-3-yl , 4 , 5-Dihydro-lH-pyrrol-2-yl , 4 , 5-Dihydro-lH-pyrrol-3-yl , 3 , 4-Dihydro-2H-pyrrol-2-yl, 3 , 4-Dihydro-2H-pyrrol-3-yl , 3 , 4-Dihydro-5H-pyrrol-2-yl , 3 , 4-Dihydro-5H-pyrrol-3-yl , 2-Furyl, 3-Furyl, 2-Thienyl, 3-Thienyl, Pyrrol-2-yl,Tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydrothien-2-yl, tetrahydrothien-3-yl, tetrahydropyrrol-2-yl, tetrahydropyrrol-3-yl, 2, 3-dihydrofuran-2-yl, 2, 3-dihydrofuran-3-yl, 2,5-dihydrofuran-2-yl, 2,5-dihydrofuran-3-yl, 4,5-dihydrofuran-2-yl, 4,5-dihydrofuran-3-yl, 2,3-dihydrothien-2- yl, 2,3-dihydrothien-3-yl, 2,5-dihydrothien-2-yl, 2,5-dihydrothien-3-yl, 4,5-dihydrothien-2-yl, 4,5-dihydrothien 3-yl, 2,3-dihydro-lH-pyrrol-2-yl, 2,3-dihydro-lH-pyrrol-3-yl, 2,5-dihydro-lH-pyrrol-2-yl, 2,5- Dihydro-lH-pyrrol-3-yl, 4,5-dihydro-lH-pyrrol-2-yl, 4,5-dihydro-lH-pyrrol-3-yl, 3,4-dihydro-2H-pyrrol-2- yl, 3,4-dihydro-2H-pyrrol-3-yl, 3,4-dihydro-5H-pyrrol-2-yl, 3,4-dihydro-5H-pyrrol-3-yl, 2-furyl, 3- Furyl, 2-thienyl, 3-thienyl, pyrrol-2-yl,
Pyrrol-3-yl, Tetrahydropyrazol-3-yl, Tetrahydropyrazol-4-yl, Tetrahydroisoxazol-3-yl, Tetrahydroisoxazol-4-yl, Tetrahy- droisoxazol-5-yl, 1, 2-Oxathiolan-3-yl, l,2-Oxathiolan-4-yl, 1, 2-Oxathiolan-5-yl, Tetrahydroisothiazol-3-yl, Tetrahydro- isothiazol-4-yl, Tetrahydroisothiazol-5-yl , 1, 2-Dithiolan-3- yl, l,2-Dithiolan-4-yl, Tetrahydroimidazol-2-yl, Tetrahydro- imidazol-4-yl, Tetrahydrooxazol-2-yl, Tetrahydrooxazol-4-yl, Tetrahydrooxazol-5-yl, Tetrahydrothiazol-2-yl, Tetrahydro- thiazol-4-yl, Tetrahydrothiazol-5-yl, 1, 3-Dioxolan-2-yl, 1, 3-Dioxolan-4-yl, 1, 3-Oxathiolan-2-yl, 1, 3-Oxathiolan-4-yl, 1, 3-Oxathiolan-5-yl, 1, 3-Dithiolan-2-yl, 1, 3-Dithiolan-4-yl, 4, 5-Dihydro-lH-pyrazol-3-yl, 4, 5-Dihydro-lH-pyrazol-4-yl, 4 , 5-Dihydro-lH-pyrazol-5-yl , 2 , 5-Dihydro-lH-pyrazol-3-yl , 2 , 5-Dihydro-lH-pyrazol-4-yl , 2 , 5-Dihydro-lH-pyrazol-5-yl , 4, 5-Dihydroisoxazol-3-yl, 4 , 5-Dihydroisoxazol-4-yl, 4,5-Dihy- droisoxazol-5-yl, 2, 5-Dihydroisoxazol-3-yl, 2, 5-Dihydroisoxa- zol-4-yl, 2, 5-Dihydroisoxazol-5-yl, 2, 3-Dihydroisoxazol-3-yl, 2, 3-Dihydroisoxazol-4-yl, 2, 3-Dihydroisoxazol-5-yl, 4,5-Dihy- droisothiazol-3-yl, 4 , 5-Dihydroisothiazol-4-yl, 4,5-Dihydro- isothiazol-5-yl, 2, 5-Dihydroisothiazol-3-yl, 2, 5-Dihydroiso- thiazol-4-yl, 2 , 5-Dihydroisothiazol-5-yl, 2 , 3-Dihydroisothia- zol-3-yl, 2 , 3-Dihydroisothiazol-4-yl, 2, 3-Dihydroisothiazol- 5-yl, Δ3-l,2-Dithiol-3-yl, Δ3-l, 2-Dithiol-4-yl , Δ3-1,2-Di- thiol-5-yl, 4 , 5-Dihydro-lH-imidazol-2-yl, 4 , 5-Dihydro-lH-imi - dazol-4-yl, 4 , 5-Dihydro-lH-imidazol-5-yl, 2 , 5-Dihydro-lH-imi - dazol-2-yl, 2 , 5-Dihydro-lH-imidazol-4-yl, 2 , 5-Dihydro-lH-imi - dazol-5-yl, 2 , 3-Dihydro-lH-imidazol-2-yl, 2 , 3-Dihydro-lH-imi- dazol-4-yl, 4, 5-Dihydrooxazol-2-yl, 4, 5-Dihydrooxazol-4-yl, 4, 5-Dihydrooxazol-5-yl, 2, 5-Dihydrooxazol-2-yl, 2,5-Dihydro- oxazol-4-yl, 2, 5-Dihydrooxazol-5-yl, 2, 3-Dihydrooxazol-2-yl, 2, 3-Dihydrooxazol-4-yl, 2, 3-Dihydrooxazol-5-yl, 4,5-Dihydro- thiazol-2-yl, 4, 5-Dihydrothiazol-4-yl, 4, 5-Dihydrothia- zol-5-yl, 2, 5-Dihydrothiazol-2-yl, 2, 5-Dihydrothiazol-4-yl, 2, 5-Dihydrothiazol-5-yl, 2, 3-Dihydrothiazol-2-yl, 2,3-Dihy- drothiazol-4-yl, 2, 3-Dihydrothiazol-5-yl, 1, 3-Dioxol-2-yl, l,3-Dioxol-4-yl, 1, 3-Dithiol-2-yl, 1, 3-Dithiol-4-yl, 1,3-Oxa- thiol-2-yl, 1, 3-Oxathiol-4-yl, 1, 3-Oxathiol-5-yl, Pyrazol-3- yl, Pyrazol-4-yl, Isoxazol-3-yl, Isoxazol-4-yl , Isoxazol-5- yl, Isothiazol-3-yl, Isothiazol-4-yl , Isothiazol-5-yl , Imidazol-2-yl, Imidazol-4-yl, Oxazol-2-yl, Oxazol-4-yl, Oxazol-5-yl, Thiazol-2-yl, Thiazol-4-yl, Thiazol-5-yl, 1,2, 3-Δ-Oxadiazolin-4-yl, 1, 2, 3-Δ2-Oxadiazolin-5-yl, 1,2, 4-Δ4-Oxadiazolin-3-yl , 1,2, 4-Δ4-Oxadiazolin-5-yl , 1,2, 4-Δ2-Oxadiazolin-3-yl , 1,2, 4-Δ-Oxadiazolin-5-yl , 1,2, 4-Δ3-Oxadiazolin-3-yl, 1,2, 4-Δ3-Oxadiazolin-5-yl , 1,3, 4-Δ2-Oxadiazolin-2-yl, 1,3, 4-Δ2-Oxadiazolin-5-yl, l,3,4-Δ3-Oxadiazolin-2-yl, 1, 3 , 4-Oxadiazolin-2-yl,Pyrrol-3-yl, tetrahydropyrazol-3-yl, tetrahydropyrazol-4-yl, tetrahydroisoxazol-3-yl, tetrahydroisoxazol-4-yl, tetrahydroisoxazol-5-yl, 1, 2-oxathiolan-3-yl, l 2-oxathiolan-4-yl, 1, 2-oxathiolan-5-yl, tetrahydroisothiazol-3-yl, tetrahydroisothiazol-4-yl, tetrahydroisothiazol-5-yl, 1, 2-dithiolan-3-yl, l, 2-dithiolan-4-yl, tetrahydroimidazol-2-yl, tetrahydroimidazol-4-yl, tetrahydrooxazol-2-yl, tetrahydrooxazol-4-yl, tetrahydrooxazol-5-yl, tetrahydro-thiazol-2-yl 4-yl, tetrahydrothiazol-5-yl, 1, 3-dioxolan-2-yl, 1, 3-dioxolan-4-yl, 1, 3-oxathiolan-2-yl, 1, 3-oxathiolan-4-yl, 1,3-oxathiolan-5-yl, 1,3-dithiolan-2-yl, 1,3-dithiolan-4-yl, 4,5-dihydro-lH-pyrazol-3-yl, 4,5-dihydro- lH-pyrazol-4-yl, 4,5-dihydro-lH-pyrazol-5-yl, 2,5-dihydro-lH-pyrazol-3-yl, 2,5-dihydro-lH-pyrazol-4-yl, 2,5-dihydro-1H-pyrazol-5-yl, 4,5-dihydroisoxazol-3-yl, 4,5-dihydroisoxazol-4-yl, 4,5-dihydroisoxazol-5-yl, 2,5- Dihydroisoxazol-3-yl, 2,5-dihydroisoxazol-4-yl,2 , 5-dihydroisoxazol-5-yl, 2,3-dihydroisoxazol-3-yl, 2,3-dihydroisoxazol-4-yl, 2,3-dihydroisoxazol-5-yl, 4,5-dihydroisothiazol-3-yl , 4,5-dihydroisothiazol-4-yl, 4,5-dihydro-isothiazol-5-yl, 2,5-dihydroisothiazol-3-yl, 2,5-dihydroisothiazol-4-yl, 2,5-dihydroisothiazole -5-yl, 2,3-dihydroisothiazol-3-yl, 2,3-dihydroisothiazol-4-yl, 2,3-dihydroisothiazol-5-yl, Δ 3 -l, 2-dithiol-3-yl, Δ 3 -l, 2-dithiol-4-yl, Δ 3 -1,2-di-thiol-5-yl, 4, 5-dihydro-lH-imidazol-2-yl, 4, 5-dihydro-lH- imi - dazol-4-yl, 4,5-dihydro-lH-imidazol-5-yl, 2,5-dihydro-lH-imi - dazol-2-yl, 2,5-dihydro-lH-imidazol-4- yl, 2,5-dihydro-lH-imi - dazol-5-yl, 2,3-dihydro-lH-imidazol-2-yl, 2,3-dihydro-lH-imi-dazol-4-yl, 4, 5-dihydrooxazol-2-yl, 4,5-dihydrooxazol-4-yl, 4,5-dihydrooxazol-5-yl, 2,5-dihydrooxazol-2-yl, 2,5-dihydrooxazol-4-yl, 2, 5-dihydrooxazol-5-yl, 2, 3-dihydrooxazol-2-yl, 2, 3-dihydrooxazol-4-yl, 2, 3-dihydrooxazol-5-yl, 4,5-dihydro-thiazol-2- yl, 4,5-dihydrothiazol-4-yl, 4,5-dihydrothiazol-5-yl, 2,5-dihydrothiazol-2-yl, 2,5-dihydrothiazol-4-yl, 2,5-dihydrothiazol-5-yl, 2,3-dihydrothiazol-2- yl, 2,3-dihydrothiazol-4-yl, 2,3-dihydrothiazol-5-yl, 1,3-dioxol-2-yl, 1,3-dioxol-4-yl, 1,3-dithiol 2-yl, 1, 3-dithiol-4-yl, 1,3-oxathiol-2-yl, 1, 3-oxathiol-4-yl, 1, 3-oxathiol-5-yl, pyrazol-3- yl, pyrazol-4-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, imidazol-2-yl, Imidazol-4-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, 1,2, 3-Δ- Oxadiazolin-4-yl, 1, 2, 3-Δ 2 -oxadiazolin-5-yl, 1,2, 4-Δ 4 -oxadiazolin-3-yl, 1,2, 4-Δ 4 -oxadiazolin-5-yl , 1,2, 4-Δ 2 -Oxadiazolin-3-yl, 1,2, 4-Δ-oxadiazoline-5-yl, 1,2, 4-Δ 3 -Oxadiazolin-yl-3, 1,2, 4 -Δ 3 -oxadiazolin-5-yl, 1,3, 4-Δ 2 -oxadiazolin-2-yl, 1,3, 4-Δ 2 -oxadiazolin-5-yl, 1,3,4-Δ 3 -oxadiazolin -2-yl, 1, 3, 4-oxadiazolin-2-yl,
1,2, 4-Δ4-Thiadiazolin-3-yl , 1,2, 4-Δ4-Thiadiazolin-5-yl , 1,2, 4-Δ3-Thiadiazolin-3-yl , 1,2, 4-Δ3-Thiadiazolin-5-yl, 1,2, 4-Δ2-Thiadiazolin-3-yl , 1,2, 4-Δ2-Thiadiazolin-5-yl , 1,3, 4-Δ2-Thiadiazolin-2-yl , 1,3, 4-Δ2-Thiadiazolin-5-yl , l,3,4-Δ3-Thiadiazolin-2-yl, 1, 3 , 4-Thiadiazolin-2-yl, 1,3, 2-Dioxathiolan-4-yl , 1,2, 3-Δ2-Triazolin-4-yl , 1,2, 3-Δ2-Triazolin-5-yl , 1,2, 4-Δ2-Triazolin-3-yl , 1,2, 4-Δ2-Triazolin-5-yl , 1,2, 4-Δ3-Triazolin-3-yl , l,2,4-Δ3-Triazolin-5-yl, 1, 2, 4-Δ1-Triazolin-2-yl, 1,2,4-Tri- azolin-3-yl, 3H-1, 2, 4-Dithiazol-5-yl, 2H-1, 3 , 4-Dithiazol-5- yl, 2H-l,3,4-Oxathiazol-5-yl, 1, 2, 3-Oxadiazol-4-yl, 1,2, 3-Oxadiazol-5-yl, 1,2, 4-Oxadiazol-3-yl, 1,2,4, -Oxadiazol-5-yl , 1,3, 4-Oxadiazol-2-yl , 1,2, 3-Thiadiazol-4-yl , 1,2, 3-Thiadiazol-5-yl , l,2,4-Thiadiazol-3-yl, 1, 2 , 4-Thiadiazol-5-yl, 1,3,4-Thia- diazolyl-2-yl, 1, 2, 3-Triazol-4-yl, 1, 2, 4-Triazol-3-yl, Tetrazol-5-yl,1,2, 4-Δ 4 -Thiadiazolin-3-yl, 1,2, 4-Δ 4 -Thiadiazolin-yl-5, 1,2, 4-Δ 3 -Thiadiazolin-yl-3, 1,2, 4 -Δ 3 -Thiadiazolin-5-yl, 1,2, 4-Δ 2 -Thiadiazolin-3-yl, 1,2, 4-Δ 2 -Thiadiazolin-5-yl, 1,3, 4-Δ 2 -Thiadiazolin -2-yl, 1,3, 4-Δ 2 -thiadiazolin-5-yl, l, 3,4-Δ 3 -thiadiazolin-2-yl, 1, 3, 4-thiadiazolin-2-yl, 1,3 , 2-dioxathiolan-4-yl, 1,2, 3-Δ 2 -triazolin-4-yl, 1,2, 3-Δ 2 -triazolin-5-yl, 1,2, 4-Δ 2 -triazolin- 3-yl, 1,2, 4-Δ 2 -triazolin-5-yl, 1,2, 4-Δ 3 -triazolin-3-yl, l, 2,4-Δ 3 -triazolin-5-yl, 1 , 2, 4-Δ 1 -triazolin-2-yl, 1,2,4-triazolin-3-yl, 3H-1, 2, 4-dithiazol-5-yl, 2H-1, 3, 4- Dithiazol-5-yl, 2H-l, 3,4-oxathiazol-5-yl, 1, 2, 3-oxadiazol-4-yl, 1,2, 3-oxadiazol-5-yl, 1,2, 4- Oxadiazol-3-yl, 1,2,4, -oxadiazol-5-yl, 1,3, 4-oxadiazol-2-yl, 1,2, 3-thiadiazol-4-yl, 1,2, 3-thiadiazole -5-yl, l, 2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,3,4-thiadiazolyl-2-yl, 1,2,3-triazole -4-yl, 1, 2, 4-triazol-3-yl, tetrazol-5-yl,
6-gliedrige Ringe wie:6-link rings such as:
Tetrahydropyran-2-yl, Tetrahydropyran-3-yl , Tetrahydro- pyran-4-yl, Piperidin-2-yl, Piperidin-3-yl, Piperidin-4-yl, Tetrahydrothiopyran-2-yl, Tetrahydrothiopyran-3-yl, Tetra- hydrothiopyran-4-yl, 2H-3 , 4-Dihydropyran-6-yl, 2H-3,4-Dihydropyran-5-yl, 2H-3 , 4-Dihydropyran-4-yl, 2H-3 , 4-Dihydropyran-3-yl , 2H-3 , 4-Dihydropyran-2-yl , 2H-3 , 4-Dihydropyran-6-yl, 2H-3 , 4-Dihydrothiopyran-5-yl, 2H-3 , 4-Dihydrothiopyran-4-yl , 2H-3 , 4-Dihydropyran-3-yl, 2H-3 , 4-Dihydropyran-2-yl , 1,2,3, 4-Tetrahydropyridin-6-yl , l,2,3,4-Tetrahydropyridin-5-yl, 1, 2, 3,4-Tetrahydropyridin-4- yl, 1,2, 3,4-Tetrahydropyridin-3-yl, 1, 2, 3 , 4-Tetrahydropyri- din-2-yl, 2H-5, 6-Dihydropyran-2-yl, 2H-5, 6-Dihydropyran-3-yl, 2H-5, 6-Dihydropyran-4-yl, 2H-5, 6-Dihydropyran-5-yl, 2H-5 , 6-Dihydropyran-6-yl , 2H-5 , 6-Dihydrothiopyran-2-yl, 2H-5, 6-Dihydrothiopyran-3-yl, 2H-5, 6-Dihydrothiopyran-4-yl, 2H-5 , 6-Dihydrothiopyran-5-yl, 2H-5 , 6-Dihydrothiopyran-6-yl , 1,2,5, 6-Tetrahydropyridin-2-yl, 1,2,5, 6-Tetrahydropyridin-3- yl, l,2,5,6-Tetrahydropyridin-4-yl, 1, 2, 5, 6-Tetrahydropyri- din-5-yl, 1, 2, 5, 6-Tetrahydropyridin-6-yl, 2 , 3 , 4, 5-Tetrahydro- pyridin-2-yl, 2, 3 , 4, 5-Tetrahydropyridin-3-yl, 2 , 3 , 4 , 5-Tetra- hydropyridin-4-yl , 2,3,4, 5-Tetrahydropyridin-5-yl , 2,3,4, 5-Tetrahydropyridin-6-yl, 4H-Pyran-2-yl, 4H-Pyran-3- yl, 4H-Pyran-4-yl, 4H-Thiopyran-2-yl, 4H-Thiopyran-3-yl, 4H-Thiopyran-4-yl, 1, 4-Dihydropyridin-2-yl, 1, 4-Dihydropyri- din-3-yl, l,4-Dihydropyridin-4-yl, 2H-Pyran-2-yl, 2H-Pyran- 3-yl, 2H-Pyran-4-yl, 2H-Pyran-5-yl, 2H-Pyran-6-yl, 2H-Thiopy- ran-2-yl, 2H-Thiopyran-3-yl, 2H-Thiopyran-4-yl, 2H-Thiopyran- 5-yl, 2H-Thiopyran-6-yl, 1, 2-Dihydropyridin-2-yl, 1, 2-Dihydropyridin-3-yl, 1, 2-Dihydropyridin-4-yl,Tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, tetrahydrothiopyran-2-yl, tetrahydrothiopyran-3-yl, Tetra-hydrothiopyran-4-yl, 2H-3, 4-dihydropyran-6-yl, 2H-3,4-dihydropyran-5-yl, 2H-3, 4-dihydropyran-4-yl, 2H-3, 4- Dihydropyran-3-yl, 2H-3, 4-dihydropyran-2-yl, 2H-3, 4-dihydropyran-6-yl, 2H-3, 4-dihydrothiopyran-5-yl, 2H-3, 4-dihydrothiopyran 4-yl, 2H-3, 4-dihydropyran-3-yl, 2H-3, 4-dihydropyran-2-yl, 1,2,3, 4-tetrahydropyridin-6-yl, l, 2,3,4- Tetrahydropyridin-5-yl, 1, 2, 3,4-tetrahydropyridin-4-yl, 1,2, 3,4-tetrahydropyridin-3-yl, 1, 2, 3, 4-tetrahydropyridin-2-yl, 2H-5, 6-dihydropyran-2-yl, 2H-5, 6-dihydropyran-3-yl, 2H-5, 6-dihydropyran-4-yl, 2H-5, 6-dihydropyran-5-yl, 2H- 5, 6-dihydropyran-6-yl, 2H-5, 6-dihydrothiopyran-2-yl, 2H-5, 6-dihydrothiopyran-3-yl, 2H-5, 6-dihydrothiopyran-4-yl, 2H-5, 6-dihydrothiopyran-5-yl, 2H-5, 6-dihydrothiopyran-6-yl, 1,2,5, 6-tetrahydropyridin-2-yl, 1,2,5, 6-tet rahydropyridine-3- yl, l, 2,5,6-tetrahydropyridin-4-yl, 1, 2, 5, 6-tetrahydropyridin-5-yl, 1, 2, 5, 6-tetrahydropyridin-6-yl, 2, 3, 4, 5-tetrahydropyridin-2-yl, 2, 3, 4, 5-tetrahydropyridin-3-yl, 2, 3, 4, 5-tetrahydropyridin-4-yl, 2,3,4, 5- Tetrahydropyridin-5-yl, 2,3,4,5-tetrahydropyridin-6-yl, 4H-pyran-2-yl, 4H-pyran-3-yl, 4H-pyran-4-yl, 4H-thiopyran-2- yl, 4H-thiopyran-3-yl, 4H-thiopyran-4-yl, 1,4-dihydropyridin-2-yl, 1,4-dihydropyridine-3-yl, 1,4-dihydropyridin-4-yl, 2H-pyran-2-yl, 2H-pyran-3-yl, 2H-pyran-4-yl, 2H-pyran-5-yl, 2H-pyran-6-yl, 2H-thiopyran-2-yl, 2H-thiopyran-3-yl, 2H-thiopyran-4-yl, 2H-thiopyran- 5-yl, 2H-thiopyran-6-yl, 1, 2-dihydropyridin-2-yl, 1, 2-dihydropyridin-3- yl, 1, 2-dihydropyridin-4-yl,
1 , 2-Dihydropyridin-5-yl , 1 , 2-Dihydropyridin-6-yl , 3 , 4-Dihydropyridin-2-yl, 3 , 4-Dihydropyridin-3-yl , 3 , 4-Dihydropyridin-4-yl, 3 , 4-Dihydropyridin-5-yl, 3 , 4-Dihydropyridin-6-yl , 2 , 5-Dihydropyridin-2-yl , 2 , 5-Dihydropyridin-3-yl , 2 , 5-Dihydropyridin-4-yl , 2 , 5-Dihydropyridin-5-yl , 2 , 5-Dihydropyridin-6-yl ,1, 2-dihydropyridin-5-yl, 1, 2-dihydropyridin-6-yl, 3, 4-dihydropyridin-2-yl, 3, 4-dihydropyridin-3-yl, 3, 4-dihydropyridin-4-yl, 3, 4-dihydropyridin-5-yl, 3, 4-dihydropyridin-6-yl, 2, 5-dihydropyridin-2-yl, 2, 5-dihydropyridin-3-yl, 2, 5-dihydropyridin-4-yl, 2, 5-dihydropyridin-5-yl, 2, 5-dihydropyridin-6-yl,
2, 3-Dihydropyridin-2-yl, 2 , 3-Dihydropyridin-3-yl, 2, 3-Dihydropyridin-4-yl, 2 , 3-Dihydropyridin-5-yl,2, 3-dihydropyridin-2-yl, 2, 3-dihydropyridin-3-yl, 2, 3-dihydropyridin-4-yl, 2, 3-dihydropyridin-5-yl,
2 , 3-Dihydropyridin-6-yl, Pyridin-2-yl, Pyridin-3-yl , Pyridin-4-yl, 1, 3-Dioxan-2-yl , 1, 3-Dioxan-4-yl , 1,3-Dioxan- 5-yl, l,4-Dioxan-2-yl, 1, 3-Dithian-2-yl, 1, 3-Dithian-4-yl, 1, 3-Dithian-5-yl, 1, 4-Dithian-2-yl , 1, 3-Oxathian-2-yl , 1, 3-Oxathian-4-yl, 1, 3-Oxathian-5-yl, 1, 3-Oxathian-6-yl, l,4-Oxathian-2-yl, 1, 4-Oxathian-3-yl, l,2-Dithian-3-yl, 1, 2-Dithian-4-yl, Hexahydropyrimidin-2-yl, Hexahydropyrimi - din-4-yl, Hexahydropyrimidin-5-yl, Hexahydropyrazin-2-yl, Hexahydropyridazin-3-yl, Hexahydropyridazin-4-yl, Tetra - hydro-1, 3-oxazin-2-yl, Tetrahydro-1, 3-oxazin-4-yl, Tetra- hydro-1, 3-oxazin-5-yl, Tetrahydro-1, 3-oxazin-6-yl, Tetra- hydro-1, 3-thiazin-2-yl, Tetrahydro-1, 3-thiazin-4-yl , Tetra - hydro-1, 3-thiazin-5-yl, Tetrahydro-1, 3-thiazin-6-yl, Tetra- hydro-1, 4-thiazin-2-yl, Tetrahydro-1, 4-thiazin-3-yl , Tetr - hydro-1, 4-oxazin-2-yl, Tetrahydro-1, 4-oxazin-3-yl, Tetra- hydro-1, 2-oxazin-3-yl, Tetrahydro-1, 2-oxazin-4-yl, Tetra - hydro-1, 2-oxazin-5-yl, Tetrahydro-1, 2-oxazin-6-yl , 2H-5,6-Di- hydro-1, 2-oxazin-3-yl, 2H-5, 6-Dihydro-l, 2-oxazin-4-yl, 2H-5, 6-Dihydro-l,2-oxazin-5-yl, 2H-5, 6-Dihydro-l, 2-oxa- zin-6-yl, 2H-5, 6-Dihydro-l,2-thiazin-3-yl, 2H-5,6-Di- hydro-l,2-thiazin-4-yl, 2H-5, 6-Dihydro-l, 2-thiazin-5-yl , 2H-5, 6-Dihydro-l,2-thiazin-6-yl, 4H-5, 6-Dihydro-l, 2-oxa- zin-3-yl, 4H-5, 6-Dihydro-l, 2-oxazin-4-yl, 4H-5 , 6-Dihydro- 1, 2-oxazin-5-yl, 4H-5, 6-Dihydro-l, 2-oxazin-6-yl, 4H-5,6-Di- hydro-l,2-thiazin-3-yl, 4H-5, 6-Dihydro-l, 2-thiazin-4-yl, 4H-5,6-Dihydro-l,2-thiazin-5-yl, 4H-5, 6-Dihydro-l, 2-thia- zin-6-yl, 2H-3, 6-Dihydro-l, 2-oxazin-3-yl, 2H-3, 6-Dihydro- l,2-oxazin-4-yl, 2H-3 , 6-Dihydro-l, 2-oxazin-5-yl , 2H-3,6-Di- hydro-1, 2-oxazin-6-yl, 2H-3 , 6-Dihydro-l, 2-thiazin-3-yl, 2H-3 , 6-Dihydro-l , 2-thiazin-4-yl , 2H-3 , 6-Dihydro-l , 2-thia- zin-5-yl, 2H-3 , 6-Dihydro-l, 2-thiazin-6-yl , 2H-3 , 4-Dihydro- l,2-oxazin-3-yl, 2H-3 , 4-Dihydro-l, 2-oxazin-4-yl, 2H-3,4-Di- hydro-1, 2-oxazin-5-yl, 2H-3 , 4-Dihydro-l, 2-oxazin-6-yl, 2H-3 , 4-Dihydro-l , 2-thiazin-3-yl , 2H-3 , 4-Dihydro-l , 2-thia- zin-4-yl, 2H-3 , 4-Dihydro-l, 2-thiazin-5-yl, 2H-3 , 4-Dihydro- 1, 2-thiazin-6-yl, 2,3,4, 5-Tetrahydropyridazin-3-yl, 2, 3 , 4 , 5-Tetrahydropyridazin-4-yl, 2, 3, 4 , 5-Tetrahydropyrida- zin-5-yl, 2, 3 , 4, 5-Tetrahydropyridazin-6-yl, 3 , 4, 5, 6-Tetrahy- dropyridazin-3-yl, 3,4,5, 6-Tetrahydropyridazin-4-yl, 1,2,5, 6-Tetrahydropyridazin-3-yl, 1,2,5, 6-Tetrahydropyrida- zin-4-yl, 1, 2, 5, 6-Tetrahydropyridazin-5-yl, 1, 2, 5, 6-Tetrahy- dropyridazin-6-yl, 1, 2 , 3 , 6-Tetrahydropyridazin-3-yl,2, 3-dihydropyridin-6-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, 1, 3-dioxan-2-yl, 1, 3-dioxan-4-yl, 1, 3-dioxan-5-yl, l, 4-dioxan-2-yl, 1,3-dithian-2-yl, 1,3-dithian-4-yl, 1,3-dithian-5-yl, 1,1 4-dithian-2-yl, 1, 3-oxathian-2-yl, 1, 3-oxathian-4-yl, 1, 3-oxathian-5-yl, 1, 3-oxathian-6-yl, l, 4-oxathian-2-yl, 1,4-oxathian-3-yl, 1,2-dithian-3-yl, 1,2-dithian-4-yl, hexahydropyrimidin-2-yl, hexahydropyrimi - din-4- yl, hexahydropyrimidin-5-yl, hexahydropyrazin-2-yl, hexahydropyridazin-3-yl, hexahydropyridazin-4-yl, tetra - hydro-1, 3-oxazin-2-yl, tetrahydro-1, 3-oxazin-4- yl, tetrahydro-1,3-oxazin-5-yl, tetrahydro-1,3-oxazin-6-yl, tetrahydro-1,3-thiazin-2-yl, tetrahydro-1,3-thiazine 4-yl, tetra-hydro-1, 3-thiazin-5-yl, tetrahydro-1, 3-thiazin-6-yl, tetrahydro-1, 4-thiazin-2-yl, tetrahydro-1, 4- thiazin-3-yl, tetr - hydro-1, 4-oxazin-2-yl, tetrahydro-1, 4-oxazin-3-yl, tetrahydro-1, 2-oxazin-3-yl, tetrahydro-1, 2-oxazin-4-yl, tetra - hydro-1, 2-oxazin-5-yl, tetrahydro -1, 2-oxazin-6-yl, 2H-5,6-dihydro-1, 2-oxazin-3-yl, 2H-5, 6-dihydro-l, 2-oxazin-4-yl, 2H -5,6-dihydro-1,2-oxazin-5-yl, 2H-5,6-dihydro-1,2,2-oxazin-6-yl, 2H-5,6-dihydro-1,2-thiazine -3-yl, 2H-5,6-di-hydro-l, 2-thiazin-4-yl, 2H-5, 6-dihydro-l, 2-thiazin-5-yl, 2H-5, 6-dihydro -l, 2-thiazin-6-yl, 4H-5, 6-dihydro-l, 2-oxazin-3-yl, 4H-5, 6-dihydro-l, 2-oxazin-4-yl, 4H -5, 6-dihydro-1, 2-oxazin-5-yl, 4H-5, 6-dihydro-l, 2-oxazin-6-yl, 4H-5,6-di-hydro-l, 2-thiazine -3-yl, 4H-5, 6-dihydro-l, 2-thiazin-4-yl, 4H-5,6-dihydro-l, 2-thiazin-5-yl, 4H-5, 6-dihydro-l , 2-thiazin-6-yl, 2H-3, 6-dihydro-l, 2-oxazin-3-yl, 2H-3, 6-dihydro- l, 2-oxazin-4-yl, 2H-3, 6-dihydro-l, 2-oxazin-5-yl, 2H-3,6-dihydro-1, 2-oxazin-6-yl, 2H- 3, 6-dihydro-l, 2-thiazin-3-yl, 2H-3, 6-dihydro-l, 2-thiazin-4-yl, 2H-3, 6-dihydro-l, 2-thiazine 5-yl, 2H-3, 6-dihydro-l, 2-thiazin-6-yl, 2H-3, 4-dihydro-l, 2-oxazin-3-yl, 2H-3, 4-dihydro-l, 2-oxazin-4-yl, 2H-3,4-dihydro-1, 2-oxazin-5-yl, 2H-3, 4-dihydro-l, 2-oxazin-6-yl, 2H-3, 4-dihydro-l, 2-thiazin-3-yl, 2H-3, 4-dihydro-l, 2-thiazin-4-yl, 2H-3, 4-dihydro-l, 2-thiazin-5- yl, 2H-3,4-dihydro-1,2-thiazin-6-yl, 2,3,4,5-tetrahydropyridazin-3-yl, 2,3,4,5-tetrahydropyridazin-4-yl,2 3, 4, 5-tetrahydropyridazin-5-yl, 2, 3, 4, 5-tetrahydropyridazin-6-yl, 3, 4, 5, 6-tetrahydropyridazin-3-yl, 3,4,5, 6-tetrahydropyridazin-4-yl, 1,2,5, 6-tetrahydropyridazin-3-yl, 1,2,5, 6-tetrahydropyridazin-4-yl, 1, 2, 5, 6-tetrahydropyridazin-5- yl, 1, 2, 5, 6-tetrahydropyridazin-6-yl, 1, 2, 3, 6-tetrahydropyridazin-3-yl,
1,2,3, 6-Tetrahydropyridazin-4-yl, 4H-5, 6-Dihydro-l, 3-oxa- zin-2-yl, 4H-5 , 6-Dihydro-l, 3-oxazin-4-yl, 4H-5,6-Di- hydro-1, 3-oxazin-5-yl, 4H-5, 6-Dihydro-l, 3-oxazin-6-yl, 4H-5 , 6-Dihydro-l , 3-thiazin-2-yl , 4H-5 , 6-Dihydro-l , 3-thia- zin-4-yl, 4H-5, 6-Dihydro-l, 3-thiazin-5-yl, 4H-5, 6-Dihydro- 1, 3-thiazin-6-yl, 3,4, 5-6-Tetrahydropyrimidin-2-yl, 3,4,5,6-Tetrahydropyrimidin-4-yl, 3,4,5,6-Tetrahydro- pyrimidin-5-yl, 3 , 4 , 5, 6-Tetrahydropyrimidin-6-yl, 1,2,3,4-Te- trahydropyrazin-2-yl, 1,2,3, 4-Tetrahydropyrazin-5-yl, 1, 2, 3 , 4-Tetrahydropyrimidin-2-yl, 1, 2, 3, 4-Tetrahydropyrimi- din-4-yl, 1,2, 3 , 4-Tetrahydropyrimidin-5-yl, 1, 2, 3 , 4-Tetra- hydropyrimidin-6-yl, 2 , 3-Dihydro-l, 4-thiazin-2-yl, 2,3-Di- hydro-1, 4-thiazin-3-yl, 2, 3-Dihydro-l, 4-thiazin-5-yl, 2,3-Di- hydro-1, 4-thiazin-6-yl, 2H-1, 2-Oxazin-3-yl, 2H-1, 2-Oxazin-4- yl, 2H-l,2-Oxazin-5-yl, 2H-1, 2-Oxazin-6-yl , 2H-1, 2-Thiazin-3- yl, 2H-l,2-Thiazin-4-yl, 2H-1, 2-Thiazin-5-yl, 2H-1, 2-Thiazin- 6-yl, 4H-l,2-Oxazin-3-yl, 4H-1, 2-Oxazin-4-yl, 4H-1, 2-Oxazin- 5-yl, 4H-l,2-Oxazin-6-yl, 4H-1, 2-Thiazin-3-yl , 4H-1,2-Thia- zin-4-yl, 4H-1 , 2-Thiazin-5-yl, 4H-1, 2-Thiazin-6-yl , 6H-l,2-Oxazin-3-yl, 6H-1, 2-Oxazin-4-yl, 6H-1, 2-Oxazin-5-yl ,1,2,3, 6-tetrahydropyridazin-4-yl, 4H-5, 6-dihydro-l, 3-oxazin-2-yl, 4H-5, 6-dihydro-l, 3-oxazin-4- yl, 4H-5,6-dihydro-1, 3-oxazin-5-yl, 4H-5, 6-dihydro-l, 3-oxazin-6-yl, 4H-5, 6-dihydro-l, 3-thiazin-2-yl, 4H-5, 6-dihydro-l, 3-thiazin-4-yl, 4H-5, 6-dihydro-l, 3-thiazin-5-yl, 4H-5, 6-dihydro-1,3-thiazin-6-yl, 3,4,5-6-tetrahydropyrimidin-2-yl, 3,4,5,6-tetrahydropyrimidin-4-yl, 3,4,5,6- Tetrahydropyrimidin-5-yl, 3, 4, 5, 6-tetrahydropyrimidin-6-yl, 1,2,3,4-tetrahydropyrazin-2-yl, 1,2,3, 4-tetrahydropyrazine-5- yl, 1, 2, 3, 4-tetrahydropyrimidin-2-yl, 1, 2, 3, 4-tetrahydropyrimidin-4-yl, 1,2, 3, 4-tetrahydropyrimidin-5-yl, 1, 2, 3,4-tetrahydropyrimidin-6-yl, 2,3-dihydro-1,4-thiazin-2-yl, 2,3-dihydro-1,4-thiazin-3-yl, 2,3- Dihydro-l, 4-thiazin-5-yl, 2,3-di-hydro-1, 4-thiazin-6-yl, 2H-1, 2-oxazin-3-yl, 2H-1, 2-oxazin- 4- yl, 2H-l, 2-oxazin-5-yl, 2H-1, 2-oxazin-6-yl, 2H-1, 2-thiazin-3- yl, 2H-l, 2-thiazin-4- yl, 2H-1, 2-thiazin-5-yl, 2H-1, 2-thiazine-6-yl, 4H-l, 2- Oxazin-3-yl, 4H-1, 2-oxazin-4-yl, 4H-1, 2-oxazin-5-yl, 4H-l, 2-oxazin-6-yl, 4H-1, 2-thiazine 3-yl, 4H-1,2-thiazin-4-yl, 4H-1, 2-thiazin-5-yl, 4H-1, 2-thiazin-6-yl, 6H-l, 2-oxazin- 3-yl, 6H-1, 2-oxazin-4-yl, 6H-1, 2-oxazin-5-yl,
6H-l,2-Oxazin-6-yl, 6H-1, 2-Thiazin-3-yl, 6H-1, 2-Thiazin-4-yl, 6H-l,2-Thiazin-5-yl, 6H-1, 2-Thiazin-6-yl, 2H-1, 3-Oxazin-2-yl , 2H-l,3-Oxazin-4-yl, 2H-1, 3-Oxazin-5-yl, 2H-1, 3-Oxazin-6-yl, 2H-l,3-Thiazin-2-yl, 2H-1, 3-Thiazin-4-yl, 2H-1, 3-Thiazin-5- yl, 2H-l,3-Thiazin-6-yl, 4H-1, 3-Oxazin-2-yl, 4H-1, 3-Oxazin-6H-1, 2-oxazin-6-yl, 6H-1, 2-thiazin-3-yl, 6H-1, 2-thiazin-4-yl, 6H-1, 2-thiazin-5-yl, 6H- 1, 2-thiazin-6-yl, 2H-1, 3-oxazin-2-yl, 2H-1, 3-oxazin-4-yl, 2H-1, 3-oxazin-5-yl, 2H-1, 3-oxazin-6-yl, 2H-l, 3-thiazin-2-yl, 2H-1, 3-thiazin-4-yl, 2H-1, 3-thiazin-5- yl, 2H-l, 3- Thiazin-6-yl, 4H-1, 3-oxazin-2-yl, 4H-1, 3-oxazin-
4-yl, 4H-1, 3-Oxazin-5-yl, 4H-1, 3-Oxazin-6-yl, 4H-1, 3-Thiazin- 2-yl, 4H-l,3-Thiazin-4-yl, 4H-1, 3-Thiazin-5-yl, 4H-1,3-Thia- zin-6-yl, 6H-1, 3-Oxazin-2-yl, 6H-1, 3-Oxazin-4-yl, 6H-l,3-Oxa- zin-5-yl, 6H-1, 3-Oxazin-6-yl, 6H-1, 3-Thiazin-2-yl, 6H-l,3-Oxazin-4-yl, 6H-1, 3-Oxazin-5-yl, 6H-1, 3-Thiazin-6-yl, 2H-l,4-Oxazin-2-yl, 2H-1, 4-Oxazin-3-yl, 2H-1, 4-Oxazin-5-yl, 2H-l,4-Oxazin-6-yl, 2H-l,4-Thiazin-2-yl, 2H-1, 4-Thiazin-3-yl, 2H-l,4-Thiazin-5-yl, 2H-1, 4-Thiazin-6-yl, 4H-1, 4-Oxazin-2-yl, 4H-l,4-Oxazin-3-yl, 4H-1, 4-Thiazin-2-yl, 4H-1, 4-Thiazin-3-yl, l,4-Dihydropyridazin-3-yl, 1, 4-Dihydropyridazin-4-yl, 1,4-Di- hydropyridazin-5-yl, 1, 4-Dihydropyridazin-6-yl, 1,4-Dihydro- pyrazin-2-yl, 1, 2-Dihydropyrazin-2-yl, 1, 2-Dihydropyrazin- 3-yl, 1, 2-Dihydropyrazin-5-yl, 1, 2-Dihydropyrazin-6-yl, l,4-Dihydropyrimidin-2-yl, 1, 4-Dihydropyrimidin-4-yl, 1,4-Di- hydropyrimidin-5-yl, 1, 4-Dihydropyrimidin-6-yl, 3,4-Dihydro- pyrimidin-2-yl, 3 , 4-Dihydropyrimidin-4-yl, 3 , 4-Dihydropyrimi- din-5-yl oder 3 , 4-Dihydropyrimidin-6-yl, Pyridazin-3-yl,4-yl, 4H-1, 3-oxazin-5-yl, 4H-1, 3-oxazin-6-yl, 4H-1, 3-thiazin- 2-yl, 4H-l, 3-thiazin-4- yl, 4H-1, 3-thiazin-5-yl, 4H-1,3-thiazin-6-yl, 6H-1, 3-oxazin-2-yl, 6H-1, 3-oxazin-4- yl, 6H-l, 3-oxazin-5-yl, 6H-1, 3-oxazin-6-yl, 6H-1, 3-thiazin-2-yl, 6H-l, 3-oxazin-4- yl, 6H-1, 3-oxazin-5-yl, 6H-1, 3-thiazin-6-yl, 2H-l, 4-oxazin-2-yl, 2H-1, 4-oxazin-3-yl, 2H-1, 4-oxazin-5-yl, 2H-1, 4-oxazin-6-yl, 2H-1, 4-thiazin-2-yl, 2H-1, 4-thiazin-3-yl, 2H-l, 4-thiazin-5-yl, 2H-1, 4-thiazin-6-yl, 4H-1, 4-oxazin-2-yl, 4H-l, 4-oxazin-3-yl, 4H- 1,4-thiazin-2-yl, 4H-1,4-thiazin-3-yl, 1,4-dihydropyridazin-3-yl, 1,4-dihydropyridazin-4-yl, 1,4-dihydropyridazin- 5-yl, 1,4-dihydropyridazin-6-yl, 1,4-dihydropyrazin-2-yl, 1,2-dihydropyrazin-2-yl, 1,2-dihydropyrazine-3-yl, 1,2- Dihydropyrazin-5-yl, 1,2-dihydropyrazin-6-yl, 1,4-dihydropyrimidin-2-yl, 1,4-dihydropyrimidin-4-yl, 1,4-dihydropyrimidin-5-yl, 1,1 4-dihydropyrimidin-6-yl, 3,4-dihydropyrimidin-2-yl, 3,4-dihydropyrimidin-4-yl, 3,4-dihydropyrimidin-5-yl or 3,4-dihydropyrimidin-6--yl yl, pyridazin-3-yl,
Pyridazin-4-yl, Pyrimidin-2-yl, Pyrimidin-4-yl, Pyrimidin-5- yl, Pyrazin-2-yl, 1, 3 , 5-Triazin-2-yl, 1, 2, 4-Triazin-3-yl, l,2,4-Triazin-5-yl, 1, 2 , 4-Triazin-6-yl , 1, 2 , 4 , 5-Tetrazin- 3-yl;Pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl, 1, 3, 5-triazin-2-yl, 1, 2, 4-triazine 3-yl, l, 2,4-triazin-5-yl, 1, 2, 4-triazin-6-yl, 1, 2, 4, 5-tetrazin-3-yl;
wobei ggf. der Schwefel der genannten Heterocyclen zu S=0 oder S(=0)2 oxidiert sein kann;where appropriate the sulfur of the heterocycles mentioned can be oxidized to S = 0 or S (= 0) 2 ;
und wobei mit einem ankondensierten Phenylring oder mit einem C3-C6-Carbocyclus oder mit einem weiteren 5- bis 6-gliedrigen Heterocyclus ein bicyclisches Ringsystem ausgebildet werden kann.and a bicyclic ring system can be formed with a fused-on phenyl ring or with a C 3 -C 6 carbocycle or with a further 5- to 6-membered heterocycle.
N-gebundenes Heterocyclyl: ein gesättigter, partiell gesät- tigter oder ungesättigter 5- oder 6-gliedriger N-gebundener heterocyclischer Ring, der mindestens einen Stickstoff und gegebenenfalls ein bis drei gleiche oder verschiedene Hetero- atome, ausgewählt aus folgender Gruppe: Sauerstoff, Schwefel oder Stickstoff enthält, also z.B.N-linked heterocyclyl: a saturated, partially saturated or unsaturated 5- or 6-membered N-linked heterocyclic ring, the at least one nitrogen and optionally one to three identical or different heteroatoms, selected from the following group: oxygen, sulfur or contains nitrogen, for example
N-gebundene 5-gliedrige Ringe wie:N-linked 5-membered rings such as:
Tetrahydropyrrol-1-yl, 2 , 3-Dihydro-lH-pyrrol-l-yl, 2,5-Di- hydro-lH-pyrrol-1-yl, Pyrrol-1-yl, Tetrahydropyrazol-1-yl, Tetrahydroisoxazol-2-yl, Tetrahydroisothiazol-2-yl, Tetra- hydroimidazol-1-yl, Tetrahydrooxazol-3-yl, Tetrahydrothia- zol-3-yl, 4, 5-Dihydro-lH-pyrazol-l-yl, 2, 5-Dihydro-lH-pyra- zol-l-yl, 2, 3-Dihydro-lH-pyrazol-l-yl, 2, 5-Dihydroisoxazol- 2-yl, 2, 3-Dihydroisoxazol-2-yl, 2, 5-Dihydroisothiazol-2-yl, 2, 3-Dihydroisoxazol-2-yl, 4, 5-Dihydro-lH-imidazol-l-yl,Tetrahydropyrrol-1-yl, 2,3-dihydro-lH-pyrrol-l-yl, 2,5-di-hydro-lH-pyrrol-1-yl, pyrrol-1-yl, tetrahydropyrazol-1-yl, tetrahydroisoxazole 2-yl, tetrahydroisothiazol-2-yl, tetrahydroimidazol-1-yl, tetrahydrooxazol-3-yl, tetrahydrothiazol-3-yl, 4,5-dihydro-lH-pyrazol-l-yl, 2,5- Dihydro-lH-pyrazol-l-yl, 2,3-dihydro-lH-pyrazol-l-yl, 2,5-dihydroisoxazol-2-yl, 2,3-dihydroisoxazol-2-yl, 2,5- Dihydroisothiazol-2-yl, 2,3-dihydroisoxazol-2-yl, 4,5-dihydro-lH-imidazol-l-yl,
2, 5-Dihydro-lH-imidazol-l-yl, 2, 3-Dihydro-lH-imidazol-l-yl , 2, 3-Dihydrooxazol-3-yl, 2, 3-Dihydrothiazol-3-yl, Pyrazol-1- yl, Imidazol-1-yl, 1, 2, 4-Δ4-Oxadiazolin-2-yl, 1, 2 ,4-Δ2-Oxa- diazolin-4-yl, 1, 2, 4-Δ3-Oxadiazolin-2-yl, 1, 3 , 4-Δ2-Oxadiazo- lin-4-yl, 1, 2 , 4-Δ5-Thiadiazolin-2-yl, 1, 2 , 4-Δ3-Thiadiazo- lin-2-yl, 1, 2 , 4-Δ2-Thiadiazolin-4-yl, 1, 3,4-Δ2-Thiadiazo- lin-4-yl, 1, 2 , 3-Δ2-Triazolin-l-yl, 1, 2 , 4-Δ2-Triazolin-l-yl, l,2,4-Δ2-Triazolin-4-yl, 1, 2 , 4-Δ3-Triazolin-l-yl, 1,2,4-Δ1- Triazolin-4-yl, 1, 2 , 3-Triazol-l-yl , 1, 2 , 4-Triazol-l-yl , Tetrazol-1-yl ;2,5-dihydro-lH-imidazol-l-yl, 2,3-dihydro-lH-imidazol-l-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrothiazol-3-yl, pyrazole 1- yl, imidazol-1-yl, 1, 2, 4-Δ 4 -oxadiazolin-2-yl, 1, 2, 4-Δ 2 -oxadiazolin-4-yl, 1, 2, 4-Δ 3 -Oxadiazolin-2-yl, 1, 3, 4-Δ 2 -Oxadiazo-lin-4-yl, 1, 2, 4-Δ 5 -Thiadiazolin-2-yl, 1, 2, 4-Δ 3 -Thiadiazo- lin-2-yl, 1, 2, 4-Δ 2 -thiadiazolin-4-yl, 1, 3,4-Δ 2 -thiadiazo-lin-4-yl, 1, 2, 3-Δ 2 -triazolin-l -yl, 1, 2, 4-Δ 2 -triazolin-l-yl, l, 2,4-Δ 2 -triazolin-4-yl, 1, 2, 4-Δ 3 -triazolin-l-yl, 1,2,4-Δ 1 - triazolin-4-yl, 1, 2, 3 -Triazol-l-yl, 1, 2, 4-triazol-l-yl, tetrazol-1-yl;
sowie N-gebundene 6-gliedrige Ringe wie:as well as N-linked 6-membered rings such as:
Piperidin-1-yl, 1, 2, 3 , 4-Tetrahydropyridin-l-yl, 1,2,5,6-Te- trahydropyridin-1-yl, 1, 4-Dihydropyridin-l-yl, 1,2-Dihydro- pyridin-1-yl, Hexahydropyrimidin-1-yl, Hexahydropyrazin-1-yl, Hexahydropyridazin-1-yl, Tetrahydro-1, 3-oxazin-3-yl, Tetra- hydro-1, 3-thiazin-3-yl, Tetrahydro-1, 4-thiazin-4-yl, Tetra- hydro-1, 4-oxazin-4-yl, Tetrahydro-1, 2-oxazin-2-yl, 2H-5,6-Di- hydro-1, 2-oxazin-2-yl, 2H-5, 6-Dihydro-l, 2-thiazin-2-yl, 2H-3 , 6-Dihydro-l , 2-oxazin-2-yl , 2H-3 , 6-Dihydro-l , 2-thiazin- oxazin-2-yl, 2H-3 , 4-Dihydro-l, 2-thiazin-2-yl, 2 , 3,4 , 5-Tetra- hydropyridazin-2-yl, 1,2,5, 6-Tetrahydropyridazin-l-yl, 1,2,5, 6-Tetrahydropyridazin-2-yl, 1,2,3, 6-Tetrahydropyrida- zin-l-yl, 3 , 4, 5, 6-Tetrahydropyrimidin-3-yl, 1, 2, 3 ,4-Tetrahy- dropyrazin-1-yl , 1,2,3, 4-Tetrahydropyrimidin-l-yl , 1, 2 , 3 , 4-Tetrahydropyrimidin-3-yl, 2, 3-Dihdro-l, 4-thiazin- 4-yl, 2H-l,2-Oxazin-2-yl, 2H-1, 2-Thiazin-2-yl, 4H-l,4-Oxa- zin-4-yl, 4H-1, 4-Thiazin-4-yl , 1, 4-Dihydropyridazin-l-yl , 1, 4-Dihydropyrazin-l-yl, 1, 2-Dihydropyrazin-l-yl, 1,4-Dihy- dropyrimidin-1-yl oder 3, 4-Dihydropyrimidin-3-yl, sowie N-ge- bundene cyclische Imide wie:Piperidin-1-yl, 1, 2, 3, 4-tetrahydropyridin-l-yl, 1,2,5,6-tetrahydropyridin-1-yl, 1, 4-dihydropyridin-l-yl, 1,2- Dihydropyridin-1-yl, hexahydropyrimidin-1-yl, hexahydropyrazin-1-yl, hexahydropyridazin-1-yl, tetrahydro-1, 3-oxazin-3-yl, tetrahydro-1, 3-thiazin-3- yl, tetrahydro-1, 4-thiazin-4-yl, tetrahydro-1, 4-oxazin-4-yl, tetrahydro-1, 2-oxazin-2-yl, 2H-5,6-dihydro 1, 2-oxazin-2-yl, 2H-5, 6-dihydro-l, 2-thiazin-2-yl, 2H-3, 6-dihydro-l, 2-oxazin-2-yl, 2H-3, 6-dihydro-l, 2-thiazine-oxazin-2-yl, 2H-3,4, 4-dihydro-l, 2-thiazin-2-yl, 2, 3,4, 5-tetrahydropyridazin-2-yl, 1,2,5, 6-tetrahydropyridazin-l-yl, 1,2,5, 6-tetrahydropyridazin-2-yl, 1,2,3, 6-tetrahydropyridazin-l-yl, 3, 4, 5, 6-tetrahydropyrimidin-3-yl, 1, 2, 3, 4-tetrahydropyrazin-1-yl, 1,2,3, 4-tetrahydropyrimidin-l-yl, 1, 2, 3, 4-tetrahydropyrimidin-3- yl, 2, 3-dihdro-l, 4-thiazine-4-yl, 2H-l, 2-oxazin-2-yl, 2H-1, 2-thiazin-2-yl, 4H-l, 4-oxa- zin-4-yl, 4H-1,4-thiazin-4-yl, 1,4-dihydropyridazin-l-yl, 1,1 4-dihydropyrazin-l-yl, 1, 2-dihydropyrazin-l-yl, 1,4-dihydropyrimidin-1-yl or 3, 4-dihydropyrimidin-3-yl, as well as N-linked cyclic imides such as:
Phthalsäureimid, Tetrahydrophthalsäureimid, Succinimid, Ma- leinimid oder Glutarimid, sowie 4 -Oxo-1, 4-dihydro- pyridin- 1-yl;Phthalimide, tetrahydrophthalimide, succinimide, maleimide or glutarimide, and also 4-oxo-1,4-dihydropyridin-1-yl;
Alle Phenylringe bzw. Heterocyclylreste sowie alle Phenylkompo- nenten in Phenyl-Ci-Cδ-alkyl, Phenoxy, Phenylcarbonyl und Phenyl - aminocarbonyl bzw. Heterocyclylkomponenten in Heterocy- clyl-Cι-C6-alkyl, Heterocyclyloxy, Heterocyclylcarbonyl und Hete- rocyclylaminocarbonyl sind, soweit nicht anders angegeben, vorzugsweise unsubstituiert oder tragen ein bis drei Halogenatome und/oder eine Nitrogruppe, einen Cyanorest und/oder einen oder zwei Methyl-, Trifluormethyl-, Methoxy- oder Trifluormethoxysub- stituenten.All phenyl rings or heterocyclyl radicals and all components in Phenylkompo- phenyl-Ci-C δ alkyl, phenoxy, phenylcarbonyl and phenyl - aminocarbonyl or Heterocyclylkomponenten in hetero- clyl-Cι-C 6 alkyl, heterocyclyloxy, heterocyclylcarbonyl, and hetero- are rocyclylaminocarbonyl unless otherwise stated, preferably unsubstituted or carry one to three halogen atoms and / or a nitro group, a cyano radical and / or one or two methyl, trifluoromethyl, methoxy or trifluoromethoxy substituents.
Als Heterocyclylreste kommen insbesondere in Betracht, 5-glied- rige aromatische Heterocyclen wie z.B. 2-Furyl, 3-Furyl, 2-Thie- nyl, 3-Thienyl, Pyrrol-2-yl, Pyrrol-3-yl, Pyrazol-3-yl, Pyra- zol-4-yl, Isoxazol-3-yl, Isoxazol-4 -yl, Isoxazol-5-yl, Isothia- zol-3-yl, Isothiazol-4-yl, Isothiazol-5-yl, Imidazol-2-yl, Imida- zol-4-yl, Oxazol-2-yl, Oxazol-4-yl, Oxazol-5-yl, Thiazol-2-yl, Thiazol-4-yl, Thiazol-5-yl, 1, 2, 4 -Triazol-3 -yl oder Tetra- zol-5-yl;Suitable heterocyclyl radicals are in particular 5-membered aromatic heterocycles such as 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, pyrrol-2-yl, pyrrol-3-yl, pyrazol-3- yl, pyrazol-4-yl, isoxazol-3-yl, isoxazol-4 -yl, isoxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, imidazole- 2-yl, imidazol-4-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, thiazol-2-yl, Thiazol-4-yl, thiazol-5-yl, 1, 2, 4 -triazol-3 -yl or tetrazol-5-yl;
5-gliedrige partiell ungesättigte Heterocyclen wie z.B. 4,5-Dihy- dro-lH-pyrazol-3-yl, 4 , 5-Dihydro-lH-pyrazol-4 -yl, 4, 5-Dihydro-lH- pyrazol-5-yl, 4 , 5 -Dihydro-isoxazol -3 -yl , 4 , 5 -Dihydroisoxa- zol-4-yl, 4 , 5-Dihydroisoxazol-5-yl, 4 , 5 -Dihydrooxazol -2 -yl , 4, 5-Dihydrooxazol-2-yl, 4, 5-Dihydrothiazol-2-yl oder 4,5-Dihy- droimidazol -2 -yl ;5-membered partially unsaturated heterocycles such as e.g. 4,5-dihydro-lH-pyrazol-3-yl, 4,5-dihydro-lH-pyrazol-4-yl, 4,5-dihydro-lH-pyrazol-5-yl, 4,5-dihydro- isoxazol -3 -yl, 4, 5-dihydroisoxazol-4-yl, 4, 5-dihydroisoxazol-5-yl, 4, 5 -dihydrooxazol -2 -yl, 4, 5-dihydrooxazol-2-yl, 4, 5-dihydrothiazol-2-yl or 4,5-dihydroimidazole -2 -yl;
5-gliedrige gesättigte Heterocyclen wie z.B. Tetrahydrofu- ran-2-yl, Tetrahydrofuran-3 -yl, Tetrahydrothien-2-yl, Tetrahydro- thien-3-yl, Tetrahydropyrrol-2-yl, Tetrahydropyrrol-3 -yl, 1, 3-Dioxolan-2-yl, 1, 3 -Dioxolan-4 -yl , 1, 3 -Oxathiolan-2 -yl, l,3-Oxathiolan-4-yl, 1, 3 -Oxathiolan-5-yl, 1, 3 -Dithiolan-2-yl oder 1,3 -Dithiolan-4-yl;5-membered saturated heterocycles such as e.g. Tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydrothien-2-yl, tetrahydro-thien-3-yl, tetrahydropyrrol-2-yl, tetrahydropyrrol-3-yl, 1,3-dioxolan-2-yl, 1,3-dioxolan-4-yl, 1,3-oxathiolan-2-yl, 1,3-oxathiolan-4-yl, 1,3-oxathiolan-5-yl, 1,3-dithiolan-2-yl or 1,3-dithiolan-4-yl;
6-gliedrige aromatische Heterocyclen wie z.B. Pyridin-2-yl, Pyri- din-3-yl, Pyridin-4 -yl, Pyrimidin-2-yl, Pyrimidin-4-yl, Pyrimi- din-5-yl, Pyrazin-2-yl, 1, 3 , 5-Triazin-2-yl, 1, 2, 4-Triazin-3-yl, 1,2,4 -Triazin-5-yl oder 1, 2, 4 -Triazin-6-yl;6-membered aromatic heterocycles such as e.g. Pyridin-2-yl, pyridine-3-yl, pyridin-4 -yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidine-5-yl, pyrazin-2-yl, 1, 3, 5-triazin-2-yl, 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl or 1,2,4-triazin-6-yl;
6-gliedrige partiell ungesättigte Heterocyclen wie z.B.6-membered partially unsaturated heterocycles such as e.g.
2H- 3 , 4 -Dihydropyran- 6 -yl , 2H- 3 , 4 -Dihydropyran- 5 -yl , 2H- 3 , 4 -Dihy- dropyran-4 -yl, 2H- 3, 4 -Dihydropyran-3 -yl, 2H-3 , 4-Dihydropy- ran-2-yl, 2H-3 , 4 -Dihydrothiopyran-6 -yl, 2H-3, 4 -Dihydrothiopy- ran-5-yl, 2H-3, 4 -Dihydrothiopyran-4 -yl, 2H-3,4 -Dihydrothiopy- ran-3-yl, 2H-3 , 4 -Dihydrothiopyran-2 -yl, 4H-5, 6-Dihydro-l, 3 -oxa- zin-2-yl, 4H-5, 6-Dihydro-l, 3 - thiazin-2-yl oder 3 , 4, 5, 6-Tetrahy- dropyrimidin-2-yl;2H- 3, 4 -dihydropyran- 6 -yl, 2H- 3, 4 -dihydropyran- 5 -yl, 2H- 3, 4 -dihy- dropyran-4 -yl, 2H- 3, 4 -dihydropyran-3 -yl, 2H-3, 4-dihydropyran-2-yl, 2H-3, 4 -dihydrothiopyran-6 -yl, 2H-3, 4 -dihydrothiopyran-5-yl, 2H-3, 4 -dihydrothiopyran-4 - yl, 2H-3,4-dihydrothiopyran-3-yl, 2H-3,4, -dihydrothiopyran-2-yl, 4H-5, 6-dihydro-l, 3-oxazin-2-yl, 4H- 5, 6-dihydro-1,3-thiazin-2-yl or 3, 4, 5, 6-tetrahydropyrimidin-2-yl;
6-gliedrige gesättigte Heterocyclen wie z.B. Tetrahydropy- ran-2-yl, Tetrahydropyran-3 -yl, Tetrahydropyran-4 -yl, Piperi- din-2-yl, Piperidin-3 -yl, Piperidin-4 -yl, Tetrahydrothiopy- ran-2-yl, Tetrahydrothiopyran-3 -yl, Tetrahydrothiopyran-4 -yl, 1, 3-Dioxan-2-yl, 1, 3 -Dioxan-4 -yl, 1, 3 -Dioxan-5-yl, 1,3-Di- thian-2-yl, 1 , 3 -Dithian-4 -yl , 1, 3 -Dithian-5 -yl, 1,3-Oxa- thian-2-yl, 1, 3 -Oxathian-4 -yl, 1, 3 -Oxathian-5-yl, Tetrahy- dro-1, 4 -Oxazin-2-yl, Tetrahydro-1, 4-oxazin-3-yl, Tetrahy- dro-l,4-thiazin-2-yl oder Tetrahydro-1, 4- thiazin-3-yl;6-membered saturated heterocycles such as e.g. Tetrahydropyran-2-yl, tetrahydropyran-3 -yl, tetrahydropyran-4 -yl, piperidine-2-yl, piperidin-3 -yl, piperidin-4 -yl, tetrahydrothiopyran-2-yl, tetrahydrothiopyran 3 -yl, tetrahydrothiopyran-4 -yl, 1, 3-dioxan-2-yl, 1, 3 -dioxan-4 -yl, 1, 3 -dioxan-5-yl, 1,3-diethyl-2- yl, 1, 3 -dithian-4 -yl, 1, 3 -dithian-5 -yl, 1,3-oxathian-2-yl, 1, 3 -Oxathian-4 -yl, 1, 3 -Oxathian- 5-yl, tetrahydro-1,4-oxazin-2-yl, tetrahydro-1,4-oxazin-3-yl, tetrahydro-1,4-thiazin-2-yl or tetrahydro-1,4 thiazin-3-yl;
Die erfindungsgemäßen Verbindungen der Formel I mit Q = Q1 werden als Verbindungen der Formel Ia, Verbindungen der Formel I mit Q = Q2 als Ib, Verbindungen der Formel I mit Q = Q3 als Ic und Verbindungen der Formel I mit Q = Q4 als Id bezeichnet. Im Hinblick auf die Verwendung der erfindungsgemäßen Verbindungen der Formel I als Herbizide haben die Variablen vorzugsweise folgende Bedeutung, und zwar jeweils für sich allein oder in Kombination:The compounds of the formula I according to the invention with Q = Q 1 are compounds of the formula Ia, compounds of the formula I with Q = Q 2 as Ib, compounds of the formula I with Q = Q 3 as Ic and compounds of the formula I with Q = Q 4 referred to as Id. With regard to the use of the compounds of the formula I according to the invention as herbicides, the variables preferably have the following meaning, individually or in combination:
X Sauerstoff oder Schwefel; insbesondere Sauerstoff;X oxygen or sulfur; especially oxygen;
R^R2 Wasserstoff, Cι-C6 -Alkyl, Hydroxy, Cι-C6 -Alkoxy, Cχ-C6 -Aikylthio, Di - (Cι-C6- lkyl) amino, wobei die Al- kylreste der fünf letztgenannten Substituienten partiell oder vollständig halogeniert sein können und/oder eine bis drei der folgenden Gruppen tragen können: Nitro, Cyano, Cι-C4-Alkoxy, C1-C4 -Alkylsulfonyl oder C1-C4 -Alkoxycarbonyl ; insbesondere Wasserstoff, C1-C4 -Alkyl wie Methyl, Ethyl, Propyl, 1-Methylethyl, Butyl, 1 -Methylbutyl oder 2-Methylbutyl, Hydroxy, Cι-C4-Alkoxy wie Methoxy, Ethoxy, Propoxy, 1-Methylethoxy, Butoxy oder 2 -Methyl - butoxy, C1-C4 -Aikylthio wie Methylthio, Ethylthio, Propylthio oder 1-Methylethylthio, oder Di(Cι-C4-al- kyl) amino wie Dimethylamino, Diethylamino, Dipropyla- mino, Dibutylamino, N-Methyl -N-ethylamino, N-Methyl- N-propylamino, N-Methyl -N-butylamino, N-Ethyl -N-propy- lamino oder N-Ethyl -N-butylamino;R ^ R 2 is hydrogen, -CC 6 alkyl, hydroxy, -C 6 alkoxy, C 6 -C 6 -alkylthio, di - (-C 6 - alkyl) amino, the alkyl radicals of the latter five substituents may be partially or fully halogenated and / or may carry one to three of the following groups: nitro, cyano, C 4 alkoxy, C 1 -C 4 alkylsulfonyl or C 1 -C 4 alkoxycarbonyl; in particular hydrogen, C 1 -C 4 alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1 -methylbutyl or 2-methylbutyl, hydroxy, Cι-C 4 alkoxy such as methoxy, ethoxy, propoxy, 1-methylethoxy, Butoxy or 2-methyl-butoxy, C 1 -C 4 -alkylthio such as methylthio, ethylthio, propylthio or 1-methylethylthio, or di (-C-C 4 -alkyl) amino such as dimethylamino, diethylamino, dipropylaamino, dibutylamino, N-methyl -N-ethylamino, N-methyl-N-propylamino, N-methyl -N-butylamino, N-ethyl -N-propylamino or N-ethyl -N-butylamino;
oderor
R1 und R2 bilden gemeinsam eine -0- (CH2)m-0- , -O- (CH2) m-S- , -S- (CH2)m-S-, -NR5- (CH2)m-NR5-, -0- (CH2)m-NR5- ,R 1 and R 2 together form a -0- (CH 2 ) m -0-, -O- (CH 2 ) m -S-, -S- (CH 2 ) m -S-, -NR5- (CH 2 ) m -NR5-, -0- (CH 2 ) m -NR5-,
-S- (CH2)m-NR5- oder - (CH2)p-Kette aus, die einen bis drei Reste aus folgender Gruppe tragen kann: Halogen, Cyano, C1-C -Alkyl oder C1-C4 -Alkoxycarbonyl; insbesondere bilden R1 und R2 gemeinsam eine -0-CH2)m-0, -O- (CH2)m-S-, -S- (CH2)m-S oder -(CH2)p--S- (CH 2 ) m -NR 5 - or - (CH 2 ) p chain, which can carry one to three radicals from the following group: halogen, cyano, C 1 -C alkyl or C 1 -C 4 -Alkoxycarbonyl; in particular R 1 and R 2 together form a -0-CH 2 ) m -0, -O- (CH 2 ) m -S-, -S- (CH 2 ) m -S or - (CH 2 ) p -
Kette aus;Chain out;
R3 Wasserstoff, Nitro, Cyano, Halogen, Ci-Cß-Alkyl,R 3 is hydrogen, nitro, cyano, halogen, Ci-C ß- alkyl,
Ci-Cß-Halogenalkyl, Cι-C6-Alkoxy, Ci-Cβ-Halogenalkoxy, Ci-Cß-Alkylthio, Cι-C6 -Halogenalkyl hio, Ci-Cδ-Alkylsul- finyl, Ci-Cß-Halogenalkylsulfinyl, Cι-C6 -Alkylsulfonyl, Cι-C6 -Halogenalkylsulfonyl, -P(=0) (Cι-C4-Alkyl) 2 oder -P(=0) (C1-C4-Alkoxy)2; insbesondere Nitro, Halogen, Cι-C4-Alkyl wie Methyl oder Ethyl, C1-C4 -Halogenalkyl wie Difluormethyl oderCi-C ß -haloalkyl, Cι-C 6 alkoxy, Ci-Cβ-haloalkoxy, Ci-C ß -Alkylthio, Cι-C 6 -haloalkyl hio, Ci-C δ -alkylsulfinyl, Ci-C ß -haloalkylsulfinyl , Cι-C 6 alkylsulfonyl, Cι-C6 haloalkylsulfonyl, -P (= 0) (Cι-C4 alkyl) 2, or -P (= 0) (C 1 -C 4 alkoxy) 2; in particular nitro, halogen, -CC 4 alkyl such as methyl or ethyl, C 1 -C 4 haloalkyl such as difluoromethyl or
Trifluormethyl, C3.-C4 -Alkoxy wie Methoxy oder Ethoxy, Cι-C4-Halogenalkoxy wie Difluormethoxy, Trifluor- methoxy, oder Chlordif luormethoxy, Cι-C4-Alkylthio wie Methylthio oder Ethylthio, C1-C -Alkylsulfonyl wie Methylsulfonyl oder Ethylsulfonyl, Cι-C4-Halogenalkylsul- fonyl wie Difluormethylsulfonyl, Trifluormethylsulfonyl oder Chlordifluormethylsulfonyl, -P(=0) (CH3) ,Trifluoromethyl, C 3 -C 4 alkoxy such as methoxy or ethoxy, Cι-C 4 haloalkoxy, such as difluoromethoxy, trifluoro- methoxy, or chlorodif luormethoxy, -C-C 4 -alkylthio such as methylthio or ethylthio, C 1 -C -alkylsulfonyl such as methylsulfonyl or ethylsulfonyl, Cι-C 4 -haloalkylsulfonyl such as difluoromethylsulfonyl, trifluoromethylsulfonyl (0) CH 3 ),
-P(=0) (CH2CH3)2, -P(=0) (OCH3)2 oder -P (=0) (OCH2CH3) 2 ;-P (= 0) (CH 2 CH 3 ) 2 , -P (= 0) (OCH 3 ) 2 or -P (= 0) (OCH 2 CH 3 ) 2 ;
R4 Halogen, wie Chlor oder Brom, oder C1-C4 -Alkyl wie Methyl oder Ethyl;R 4 halogen, such as chlorine or bromine, or C 1 -C 4 alkyl such as methyl or ethyl;
R5 Wasserstoff oder Cι-C -Alkyl, wie Methyl oder Ethyl;R 5 is hydrogen or -CC alkyl, such as methyl or ethyl;
1 0 oder 1; m 2, 3 oder 4 ;1 0 or 1; m 2, 3 or 4;
p 4 oder 5p 4 or 5
Q ein Rest der Formel Q1, Q2, Q3 oder Q4 Q is a radical of the formula Q 1 , Q 2 , Q 3 or Q 4
R6 Hydroxy, Mercapto, Halogen, OR13, SR13, S02R14< OS02R14, OPOR15R16, OPR15R16, OPSR15R16, NR17R18, ONR18R19, N-gebun- denes Heterocyclyl oder O- (N-gebundenes Heterocyclyl) , wobei der Heterocyclyl -Rest der beiden letztgenannten Substituenten partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann:R 6 hydroxy, mercapto, halogen, OR 13 , SR 13 , S0 2 R 14 <OS0 2 R 14 , OPOR 15 R 16 , OPR 15 R 16 , OPSR 15 R 16 , NR 17 R 18 , ONR 18 R 19 , N -bound heterocyclyl or O- (N-linked heterocyclyl), where the heterocyclyl radical of the latter two substituents can be partially or completely halogenated and / or can carry one to three of the following radicals:
Nitro , Cyano, C1 - C4 -Alkyl , C1 -C4 -Halogenalkyl ,Nitro, cyano, C 1 - C 4 alkyl, C 1 -C 4 haloalkyl,
C3. - C4 -Alkoxy oder Cι - C4 -Halogenalkoxy;C 3. - C 4 alkoxy or -C - C 4 haloalkoxy;
R^R^R11 Wasserstoff, Halogen, Cyano, Cι-C6-Alkyl,R ^ R ^ R 11 is hydrogen, halogen, cyano, -CC 6 alkyl,
Ci-Cß-Halogenalkyl, Di- (Cι-C6- alkoxy) -methyl,Ci-C ß -haloalkyl, di- (-C-C 6 - alkoxy) methyl,
Di- (Cι-C6 -aikylthio) -methyl, (CX-CÖ -Alkoxy) (Cι-C6-alkyl- thio) -methyl, Hydroxy, Ci-Cg-Alkoxy, Ci-Cδ-Halogen- alkoxy, Ci -C6-Alkoxycarbonyloxy, Ci-Cö-Alkylthio,Di- (-C-C 6 -alkylthio) -methyl, (CX-C Ö -alkoxy) (Cι-C 6 -alkyl-thio) -methyl, hydroxy, Ci-Cg-alkoxy, Ci-C δ -haloalkoxy , Ci -C 6 alkoxycarbonyloxy, Ci-C ö alkylthio,
Cι-C6-Halogenalkylthio, Ci-Cβ-Alkylsulfonyl , Cι-C6-Halogenalkylsulfonyl , Ci-Cß-Alkylcarbonyl , Ci-Cö-Halogenalkylcarbonyl, Cι-C6-Alkoxycarbonyl oder Ci-Cδ-Halogenalkoxycarbonyl ;Cι-C 6 haloalkylthio, Ci-Cβ alkylsulfonyl, Cι-C 6 haloalkylsulfonyl, Ci-C ß alkylcarbonyl, Ci-C ö -haloalkylcarbonyl, Cι-C 6 -alkoxycarbonyl or C δ haloalkoxycarbonyl;
R8,R10,R12 Wasserstoff oder Ci -C6-Alkyl; insbesondere Wasserstoff oder Cι-C4-Alkyl, wie Methyl oder Ethyl;R 8 , R 10 , R 12 are hydrogen or Ci -C 6 alkyl; in particular hydrogen or -CC 4 alkyl, such as methyl or ethyl;
oder R7 und R8 oder R9 und R10 oder R11 und R12 bilden gemeinsam eine -0- (CH2)u-0-, -O- (CH2)U-S-, -S- (CH2)U-S-, -0-(CH2)v- oder -S- (CH2) V-Kette, die durch einen bis drei Reste aus folgender Gruppe substituiert sein kann: Halogen, Cyano, C1-C4 -Alkyl, C1-C4 -Halogenalkyl oderor R 7 and R 8 or R 9 and R 10 or R 11 and R 12 together form a -0- (CH 2 ) u -0-, -O- (CH 2 ) U -S-, -S- (CH 2 ) U -S-, -0- (CH 2 ) v - or -S- (CH 2 ) V chain, which can be substituted by one to three radicals from the following group: halogen, cyano, C 1 -C 4 - Alkyl, C 1 -C 4 haloalkyl or
Ci -C4 -Alkoxycarbonyl ;Ci -C 4 alkoxycarbonyl;
oderor
R7 und R8 oder R9 und R10 oder R11 und R12 bilden gemeinsam eineR 7 and R 8 or R 9 and R 10 or R 11 and R 12 together form one
- (CH2)W-Kette, die durch Sauerstoff oder Schwefel unterbrochen sein kann und/oder durch einen bis vier Reste aus folgender Gruppe substituiert sein kann: Halogen, Cyano, C1-C4 -Alkyl, C1-C4 -Halogenalkyl oder C1-C4 -Alkoxycarbonyl ;- (CH 2 ) W chain, which can be interrupted by oxygen or sulfur and / or can be substituted by one to four radicals from the following group: halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 - Haloalkyl or C 1 -C 4 alkoxycarbonyl;
oderor
R7 und R8 oder R9 und R10 oder R11 und R12 bilden gemeinsam mit dem Kohlenstoff an den sie gebunden sind eine Carbonyl- gruppe aus;R 7 and R 8 or R 9 and R 10 or R 11 and R 12 together with the carbon to which they are attached form a carbonyl group;
oderor
R7 und R9 oder R9 und R11 oder R7 und R11 bilden gemeinsam eineR 7 and R 9 or R 9 and R 11 or R 7 and R 11 together form one
- (CH ) V-Kette, die durch einen bis drei Reste aus folgender Gruppe substituiert sein kann:- (CH) V chain, which can be substituted by one to three radicals from the following group:
Halogen, Cι-C6-Alkyl, Cχ-C6-Alkoxy, Hydroxy oder Ci -C6 -Alkoxycarbonyl ;Halogen, -CC 6 alkyl, Cχ-C 6 alkoxy, hydroxy or Ci -C 6 alkoxycarbonyl;
R13 Ci-Cε-Alkyl, C3-C6-Alkenyl, C3-C6-Halogenalkenyl , C3-C6-Alkinyl, Ci-Cε-Alkylcarbonyl, C2-C6~Alkenyl- carbonyl, C3-C6-Cycloalkylcarbonyl , Ci-Cδ-Alkylamino- carbonyl, Ci-Cg-Alkylcarbonyl-Ci-Cβ-alkyl oder Ci-Cß-Alkoxyimino-Ci-Cg-alkyl, wobei die genanntenR 13 Ci-Cε-alkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, Ci-Cε-alkylcarbonyl, C 2 -C 6 ~ alkenylcarbonyl, C 3 -C 6 -cycloalkylcarbonyl, Ci-C δ -alkylamino-carbonyl, Ci-Cg-alkylcarbonyl-Ci-Cβ-alkyl or Ci-C ß -alkoxyimino-Ci-Cg-alkyl, the said
Alkyl- und Cycloalkylreste partiell oder vollständig halogeniert sein können und/oder eine bis drei der folgenden Gruppen tragen können: Cyano, Cι-C4-Alkoxy, Cι-C -Alkylthio, Cι~C4-Alkyl- carbonyl, Cι-C4~Alkoxycarbonyl, Hydroxycarbonyl ,Alkyl and cycloalkyl radicals can be partially or completely halogenated and / or can carry one to three of the following groups: cyano, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkyl carbonyl, C 1 -C 4 ~ Alkoxycarbonyl, hydroxycarbonyl,
Di- (Cι-C4-alkyl) -aminocarbonyl, Cχ-C4-Alkylcarbonyloxy oder C3-C6-Cycloalkyl;Di (C 1 -C 4 alkyl) aminocarbonyl, Cχ C 4 alkylcarbonyloxy or C 3 -C 6 cycloalkyl;
Phenyl, Heterocyclyl, Phenyl-Ci-Cδ-alkyl, Heterocy- clyl-Ci-Cß-alkyl, Phenylcarbonyl oder Heterocyclylcar- bonyl, wobei der Phenyl- und der Heterocyclyl-Rest der 6 letztgenannten Substituenten partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann:Phenyl, heterocyclyl, phenyl-Ci-C δ- alkyl, heterocyclyl-Ci-C ß- alkyl, phenylcarbonyl or heterocyclylcarbonyl, the phenyl and heterocyclyl radical being the 6 latter substituents can be partially or completely halogenated and / or can carry one to three of the following radicals:
Nitro, Cyano, Cι-C4~Alkyl, Cι-C4-Halogenalkyl, Cι-C4-Alkoxy oder Cι-C4-Halogenalkoxy;Nitro, cyano, C ~ 4 alkyl, Cι-C4-haloalkyl, Cι-C 4 alkoxy or Cι-C 4 haloalkoxy;
R1 ,R15,R16 Cι-C6-Alkyl, C3-C6-Alkenyl, C3-C6-Halogenalkenyl ,R 1 , R 15 , R 16 -CC 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl,
C3-C6-Cycloalkyl, Hydroxy, Ci-Cß-Alkoxy, Di -Ci-Cε-alkyl- amino, oder Di- (Cχ-Cg-halogenalkyl) amino, wobei die ge- nannten Alkyl-, Cycloalkyl- und Alkoxyreste partiell oder vollständig halogeniert sein können und/oder eine bis drei der folgenden Gruppen tragen können: Cyano, Cι-C4-Alkoxy, Cι-C4-Alkylthio, Cι-C4~Alkyl- carbonyl oder Cχ-C4-Alkoxycarbonyl;C 3 -C 6 cycloalkyl, hydroxy, Ci-C ß- alkoxy, di-Ci-Cε-alkylamino, or di- (Cχ-Cg-haloalkyl) amino, where the said alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and / or may carry one to three of the following groups: cyano, C 4 -alkoxy, C 4 alkylthio, Cι-C4 ~ alkyl carbonyl or Cχ-C 4 -alkoxycarbonyl ;
Phenyl, Heterocyclyl, Phenoxy oder Heterocyclyloxy, wobei der Phenyl- und der Heterocyclyl-Rest der letztgenannten Substituenten partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann:Phenyl, heterocyclyl, phenoxy or heterocyclyloxy, where the phenyl and heterocyclyl radicals of the latter substituents can be partially or completely halogenated and / or can carry one to three of the following radicals:
Nitro, Cyano, Cι-C4-Alkyl, Cι-C4-Halogenalkyl, Cι~C4-Alkoxy oder Cχ-C4-Halogenalkoxy;Nitro, cyano, C 4 -alkyl, C 4 haloalkyl, Cι ~ C4 alkoxy or Cχ-C 4 haloalkoxy;
R17 Cι-C6-Alkyl, C3 -C6-Alkenyl, C3 -C6-Halogenalkenyl , C3-C6-Cycloalkyl, Cι-C6 -Alkoxy oder C3-C6-Alkenyloxy, wobei die genannten Alkyl-, Cycloalkyl- und Alkoxyreste partiell oder vollständig halogeniert sein können und/ oder einen bis drei Reste der folgenden Gruppe tragen können: Cyano, Cι-C4-Alkoxy oder Cι-C4-Alkylthio;R 17 Cι-C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 cycloalkyl, Cι-C 6 alkoxy or C 3 -C 6 alkenyloxy, wherein the said alkyl, cycloalkyl and alkoxy radicals can be partially or completely halogenated and / or can carry one to three radicals from the following group: cyano, C 1 -C 4 alkoxy or C 1 -C 4 alkylthio;
Phenyl, Heterocyclyl, Phenyl -Cι-C6-alkyl oder Hetero- cyclyl-Cι-C6-alkyl, wobei der Phenyl- oder Heterocyclyl-Rest der vier letztgenannten Substituenten partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann: Nitro, Cyano, Cι-C4-Alkyl, C1-C4 -Halogenalkyl, C1-C4 -Alkoxy oder Cι-C4-Halogenalkoxy;Phenyl, heterocyclyl, phenyl -C 1 -C 6 alkyl or heterocyclic C 1 -C 6 alkyl, where the phenyl or heterocyclyl radical of the four last-mentioned substituents can be partially or completely halogenated and / or one to three of the following can carry radicals: nitro, cyano, C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or Cι-C 4 haloalkoxy;
R18, R19 Cι-C6-Alkyl oder C3 -C6 -Alkenyl;R 18 , R 19 -CC 6 alkyl or C 3 -C 6 alkenyl;
u 2 bis 4;u 2 to 4;
v 1 bis 5;v 1 to 5;
w 2 bis 5; R20 ein Rest wie unter R6 genannt;w 2 to 5; R 20 is a radical as mentioned under R 6 ;
R21 Wasserstoff, Cι-C6-Alkyl oder Ci-Cδ -Halogenalkyl; insbesondere Wasserstoff oder Cι-C4-Alkyl wie Methyl, Ethyl, Propyl, 1 -Methyl -eth- 1-yl , oder 1, 1-Dimethyl - eth-l-yl;R 21 is hydrogen, -CC 6 alkyl or Ci-C δ haloalkyl; in particular hydrogen or -CC 4 alkyl such as methyl, ethyl, propyl, 1-methyl-eth-1-yl, or 1, 1-dimethyl-eth-l-yl;
R22 Wasserstoff oder Ci -C6-Alkyl; insbesondere Wasserstoff oder Cι-C4-Alkyl, wie Methyl oder Ethyl;R 22 is hydrogen or Ci -C 6 alkyl; in particular hydrogen or -CC 4 alkyl, such as methyl or ethyl;
R23 Cι-C6 -Alkyl, Ci-Cε -Halogenalkyl , C3 -C6 -Cycloalkyl oder C3 -C6 -Halogencycloalkyl ; insbesondere Cι-C6-Alkyl oder C3 -C6-Cycloalkyl; außerordentlich Cyclopropyl;R 23 C 1 -C 6 alkyl, Ci-Cε haloalkyl, C 3 -C 6 cycloalkyl or C 3 -C 6 halocycloalkyl; in particular Cι-C 6 alkyl or C 3 -C 6 cycloalkyl; extremely cyclopropyl;
R24 Wasserstoff;R 24 is hydrogen;
R25 Cι-C6 -Alkyl, Cι-C6 -Halogenalkyl, C3 -C6-Cycloalkyl oder C3-C6-Halogencycloalkyl; insbesondere Ci-Cβ-Alkyl oder C3 -C6-Cycloalkyl;R 25 Cι-C 6 -alkyl, C 6 haloalkyl, C 3 -C 6 -cycloalkyl or C 3 -C 6 halocycloalkyl; in particular Ci-Cβ-alkyl or C 3 -C 6 cycloalkyl;
Besonders bevorzugt sind die Verbindungen la, insbesonders die Verbindungen la, wobei die Variablen folgende Bedeutung haben, und zwar für sich allein oder in Kombination:The compounds la are particularly preferred, in particular the compounds la, where the variables have the following meaning, individually or in combination:
R6 Hydroxy, Mercapto, Halogen, OR13, SR13, S02R14- OS02R14, NR17R18, ONR18R19 oder N-gebundenes Heterocyclyl, wobei der Heterocyclyl -Rest des letztgenannten Substituenten partiell oder vollständig halogeniert sein kann und/ oder einen bis drei der folgenden Reste tragen kann: Nitro, Cyano, Cι-C4-Alkyl, C1-C4 -Halogenalkyl, Cι-C4-Alkoxy oder C1-C4 -Halogenalkoxy;R 6 is hydroxy, mercapto, halogen, OR 13 , SR 13 , S0 2 R 14 - OS0 2 R 14 , NR 17 R 18 , ONR 18 R 19 or N-linked heterocyclyl, the heterocyclyl radical of the latter substituent being partially or completely Cι-C nitro, cyano, C 4 alkyl, C 1 -C 4 haloalkyl, 4 alkoxy or C 1 -C 4 -haloalkoxy; may be halogenated and / or may carry one to three of the following radicals
R7,R9,RU Wasserstoff, Halogen, Cyano, Cι-C6-Alkyl,R 7 , R 9 , R U are hydrogen, halogen, cyano, C 1 -C 6 -alkyl,
Cι-C6-Halogenalkyl, Di- (Ci-Cε- alkoxy) -methyl, Di- (Cι-C6-alkylthio) -methyl, (Cι-C6-Alkoxy) (Cι-C6-alkyl - thio) -methyl, Hydroxy, Ci-Cß-Alkoxy, Ci-Cδ-Halogen- alkoxy, Cι-C6-Alkoxycarbonyloxy, Ci-Cε-Alkylthio oder Ci-Cß-Halogenalkylthio;-C-C 6 -haloalkyl, di- (Ci-Cε-alkoxy) -methyl, di- (Cι-C 6 -alkylthio) -methyl, (Cι-C 6 -alkoxy) (Cι-C 6 -alkyl - thio) -methyl, hydroxy, Ci-C ß -alkoxy, Ci-C δ -haloalkoxy, Cι-C 6 -alkoxycarbonyloxy, Ci-Cε-alkylthio or Ci-C ß -haloalkylthio;
R8,R10,R12 Wasserstoff oder Ci -C6-Alkyl; insbesondere Wasserstoff oder C1-C4 -Alkyl, wie Methyl oder Ethyl;R 8 , R 10 , R 12 are hydrogen or Ci -C 6 alkyl; in particular hydrogen or C 1 -C 4 alkyl, such as methyl or ethyl;
oder R9 und R10 bilden gemeinsam mit dem Kohlenstoff an dem sie gebunden sind eine Carbonylgruppe aus;or R 9 and R 10 together with the carbon to which they are attached form a carbonyl group;
oderor
R7 und R11 bilden gemeinsam eine - (CH ) V-Kette, die ggf. durch ein bis drei Cι-C -Alkylreste substituiert ist;R 7 and R 11 together form a - (CH) V chain, which is optionally substituted by one to three -CC alkyl radicals;
R13 Cι-C6-Alkyl, C3-C6-Alkenyl, C3-C6-Halogenalkenyl, C3-C6-Alkinyl, Cι-C6-Alkylcarbonyl, C3-C6-Cycloalkyl- carbonyl, Cι-C6-Alkylaminocarbonyl, N,N-Di- (Ci-Cδ- l- kyl) oder Cι-C6-Alkylcarbonyl-Cι-C6-alkyl, wobei die genannten Alkyl- oder Cycloalkylreste partiell oder vollständig halogeniert sein können und/oder eine bis drei der folgenden Gruppen tragen können:R 13 Cι-C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, Cι-C 6 alkylcarbonyl, C 3 -C 6 -cycloalkyl- carbonyl, C 1 -C 6 -alkylaminocarbonyl, N, N-di- (Ci-C δ - 1-alkyl) or C 1 -C 6 -alkylcarbonyl-C 6 -C 6 -alkyl, the alkyl or cycloalkyl radicals mentioned being partially or completely halogenated can and / or can carry one to three of the following groups:
Cyano, Cι-C-Alkoxy, Cι-C4-Alkylthio, Cι-C-Alkyl- carbonyl, C1-C4-Alkoxycarbonyl, Hydroxycarbonyl , Di- (Cι-C4-alkyl ) -aminocarbonyl , Cι-C4-Alkylcarbonyloxy oder C3-C6-Cycloalkyl;Cyano, C alkoxy, Cι-C 4 alkylthio, Cι-C alkyl-carbonyl, C 1 -C 4 -alkoxycarbonyl, hydroxycarbonyl, di- (Cι-C4 alkyl) aminocarbonyl, Cι-C 4 -Alkylcarbonyloxy or C 3 -C 6 cycloalkyl;
Phenyl, Heterocyclyl, Phenyl-Ci-Cβ-alkyl, Heterocy- clyl-Cι-C6-alkyl, Phenylcarbonyl oder Heterocyclylcar- bonyl, wobei der Phenyl- und der Heterocyclyl-Rest der 6 letztgenannten Substituenten partiell oder vollstän- dig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann:Phenyl, heterocyclyl, phenyl-C 1 -C 6 -alkyl, heterocyclyl-C 1 -C 6 -alkyl, phenylcarbonyl or heterocyclylcarbonyl, where the phenyl and heterocyclyl radicals of the 6 latter substituents can be partially or completely halogenated and / or can carry one to three of the following residues:
Nitro, Cyano, C1-C4-Alkyl, Cι~C4-Halogenalkyl , Cι-C4-Alkoxy oder Cχ-C4-Halogenalkoxy;Nitro, cyano, C 1 -C 4 -alkyl, C ~ 4 haloalkyl, Cι-C 4 alkoxy or Cχ-C 4 haloalkoxy;
R14 Cι-C6-Alkyl, C3-C6-Alkenyl, C3-C6-Halogenalkenyl,R 14 -CC 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl,
C3-C6-Cycloalkyl, Hydroxy, Cι-C6-Alkoxy, Di - (Cι-C6-al- kyl) amino oder Di- (Ci-Cβ-halogenalkyl) amino, wobei die genannten Alkyl-, Cycloalkyl- und Alkoxyreste partiell oder vollständig halogeniert sein können und/oder eine bis drei der folgenden Gruppen tragen können:C 3 -C 6 -cycloalkyl, hydroxy, Cι-C6 alkoxy, di - (Cι-C 6 -AL- alkyl) amino or di- (Ci-Cβ-haloalkyl) amino, wherein the said alkyl, cycloalkyl and alkoxy radicals can be partially or completely halogenated and / or can carry one to three of the following groups:
Cyano, Cι-C -Alkoxy, Cx^-Alkylthio, Cι-C4-Alkyl- carbonyl oder C1-C4-Alkoxycarbonyl;Cyano, -CC alkoxy, Cx ^ alkylthio, -C 4 alkyl carbonyl or C 1 -C 4 alkoxycarbonyl;
Phenyl, Heterocyclyl, Phenoxy oder Heterocyclyloxy, wo- bei der Phenyl- und der Heterocyclyl-Rest der letztgenannten Substituenten partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann:Phenyl, heterocyclyl, phenoxy or heterocyclyloxy, where the phenyl and heterocyclyl radicals of the latter substituents can be partially or completely halogenated and / or can carry one to three of the following radicals:
Nitro, Cyano, Cι-C4-Alkyl, Cι-C4-Halogenalkyl, C1-C4-Alkoxy oder Cι-C4-Halogenalkoxy; R17 Cι-C6 -Alkyl, C3-C6 -Alkenyl, C3 -C6 -Halogenalkenyl,Nitro, cyano, C 4 -alkyl, C 4 haloalkyl, C 1 -C 4 alkoxy or Cι-C 4 haloalkoxy; R 17 -CC 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl,
C3-C6 -Cycloalkyl, Cι-C6-Alkoxy oder C3-C6"Alkenyloxy, wobei die genannten Alkyl-, Cycloalkyl- und Alkoxyreste partiell oder vollständig halogeniert sein können und/ oder einen bis drei Reste der folgenden Gruppe tragen können.- Cyano, C1-C4 -Alkoxy oder C1-C4 -Aikylthio;C 3 -C 6 cycloalkyl, -C-C 6 alkoxy or C 3 -C 6 "alkenyloxy, where the alkyl, cycloalkyl and alkoxy radicals mentioned can be partially or completely halogenated and / or carry one to three radicals from the following group - Cyano, C 1 -C 4 alkoxy or C 1 -C 4 alkylthio;
Phenyl, Heterocyclyl, Phenyl -Cι-C6 -alkyl oder Hetero- cyclyl-Ci-Cδ- alkyl, wobei der Phenyl- oder Heterocyclyl-Rest der vier letztgenannten Substituenten partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann: Nitro, Cyano, Cι-C4-Alkyl, Cχ-C4 -Halogenalkyl, Cι-C4-Alkoxy oder C1-C4 -Halogenalkoxy;Phenyl, heterocyclyl, phenyl -C-C 6 alkyl or heterocyclic-Ci-C δ - alkyl, where the phenyl or heterocyclyl radical of the four last-mentioned substituents can be partially or completely halogenated and / or one to three of the following can carry radicals: nitro, cyano, C 4 alkyl, Cχ-C4-haloalkyl, Cι-C 4 -alkoxy or C 1 -C 4 -haloalkoxy;
Ri8 Ri9 Cι-C6-Alkyl oder C3 -C6-Alkenyl; R i8 R i9 -CC 6 alkyl or C 3 -C 6 alkenyl;
v 1 oder 2; insbesondere 2;v 1 or 2; especially 2;
Ebenso besonders bevorzugt sind Verbindungen der Formel la, wobeiLikewise particularly preferred are compounds of formula la, wherein
R6 Hydroxy, Mercapto, Phenylcarbonyloxy, Cι-C6-Alkylthio, Phenylthio, N- (Cι-C6 -Alkoxy) -N- (Cx-Cö- alkyl) amino, 1-Tetrahydropyrrolyl oder 2-Tetrahydroisoxazolyl, wobei die Phenylreste der voranstehenden Reste partiell oder vollständig halogeniert sein können und/oder einen bis drei der folgenden Reste tragen können:R 6 hydroxy, mercapto, phenylcarbonyloxy, -C-C 6 -alkylthio, phenylthio, N- (-C-C 6 -alkoxy) -N- (Cx-Cö- alkyl) amino, 1-tetrahydropyrrolyl or 2-tetrahydroisoxazolyl, the phenyl radicals of the above radicals can be partially or completely halogenated and / or can carry one to three of the following radicals:
Nitro, Cyano, C1-C -Alkyl, C1-C4 -Halogenalkyl, C;L-C4-Alkoxy oder C1-C4 -Halogenalkoxy; insbesondere Hydroxy, Phenylcarbonyloxy, C1-C4-Aikylthio, Phenylthio, N- (C1-C4 -Alkoxy) -N- (C1-C4 -al- kyl) amino, 1-Tetrahydropyrrolyl oder 2-Tetrahydroisoxa- zolyl;Nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C; L -C 4 alkoxy or C 1 -C 4 haloalkoxy; in particular hydroxy, phenylcarbonyloxy, C 1 -C 4 -alkylthio, phenylthio, N- (C 1 -C 4 -alkoxy) -N- (C 1 -C 4 -alkyl) amino, 1-tetrahydropyrrolyl or 2-tetrahydroisoxa- zolyl;
R7,R8,R9,R10,R1:l,R12 Wasserstoff oder C1-C4 -Alkyl, wie Methyl oder Ethyl; insbesondere Wasserstoff oder Methyl;R 7 , R 8 , R 9 , R 10 , R 1: 1 , R 12 are hydrogen or C 1 -C 4 alkyl, such as methyl or ethyl; especially hydrogen or methyl;
oderor
R9 und R10 bilden gemeinsam mit dem Kohlenstoff an den sie gebun- den sind eine Carbonylgruppe aus; oderR 9 and R 10 together with the carbon to which they are attached form a carbonyl group; or
R7 und R11 bilden gemeinsam eine - (CH2) - oder - (CH2) 2-Kette aus;R 7 and R 11 together form a - (CH 2 ) - or - (CH 2 ) 2 chain;
Außerordentlich bevorzugt sind die Verbindungen der Formel la, wobeiThe compounds of the formula Ia are extraordinarily preferred, where
R6 Hydroxy, Mercapto, Phenylcarbonyloxy, Cχ-C6 -Aikylthio,R 6 hydroxy, mercapto, phenylcarbonyloxy, Cχ-C 6 -alkylthio,
Phenylthio, wobei die Phenylreste der voranstehenden substituierten partiell oder vollständig halogeniert sein können und/oder eine bis drei der folgenden Reste tragen können:Phenylthio, where the phenyl radicals of the above substituted can be partially or completely halogenated and / or can carry one to three of the following radicals:
Nitro, Cyano, Cι-C4-Alkyl, C1-C4 -Halogenalkyl, C1-C4-AI- koxy oder Ci-C4-Halogenalkoxy; insbesondere Hydroxy oder Phenylthio, wobei der Phenyl - rest partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann;Nitro, cyano, C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 -alkoxy -AI- or Ci-C 4 haloalkoxy; in particular hydroxy or phenylthio, where the phenyl radical can be partially or completely halogenated and / or can carry one to three of the following radicals;
Nitro, Cyano, C1-C4 -Alkyl, C1-C -Halogenalkyl, C1-C4-AI- koxy oder C1-C4-Halogenalkoxy;Nitro, cyano, C 1 -C 4 alkyl, C 1 -C haloalkyl, C 1 -C 4 -alkoxy or C1-C4-haloalkoxy;
Ebenso bevorzugt sind die Verbindungen Ib, insbesondere die Verbindungen Ib, wobei die Variablen folgende Bedeutung haben:Likewise preferred are the compounds Ib, in particular the compounds Ib, where the variables have the following meaning:
R20 ein Rest wie unter R6 genannt;R 20 is a radical as mentioned under R 6 ;
R21 Wasserstoff, Cι-C6-Alkyl oder Ci -C6-Halogenalkyl,• insbesondere C1-C4 -Alkyl, wie Methyl, Ethyl, 1 -Methyl - eth-l-yl, oder 1, l,Dimethyleth-l-yl, oder Cι-C -Halo- genalkyl wie 2-Fluorethyl oder 2, 2, 2 -Trifluorethyl;R 21 are hydrogen, C 6 alkyl or Ci-C6 haloalkyl, • in particular C 1 -C 4 alkyl such as methyl, ethyl, 1-methyl - eth-l-yl, or 1, l, Dimethyleth- l-yl, or -CC haloalkyl such as 2-fluoroethyl or 2, 2, 2-trifluoroethyl;
R22 Wasserstoff, Cι-C6 -Alkyl oder Cι-C6-Halogenalkyl, insbesondere Wasserstoff, C1-C4 -Alkyl, wie Methyl oder Ethyl, oder C1-C4-Halogenalkyl wie Trifluormethyl ; insbesondere Wasserstoff, Methyl oder Trifluormethyl;R 22 are hydrogen, C 6 alkyl or Cι-C 6 haloalkyl, in particular hydrogen, C 1 -C 4 alkyl, such as methyl or ethyl, or C 1 -C 4 haloalkyl such as trifluoromethyl; in particular hydrogen, methyl or trifluoromethyl;
Ebenso bevorzugt sind die Verbindungen Ib, wobei die Variablen folgende Bedeutung haben:Compounds Ib are likewise preferred, the variables having the following meaning:
R20 Hydroxy, Mercapto, Halogen, OR13, SR13, S02R14, OS02R14, NR17R18, ONR18R19 oder N-gebundenes Heterocyclyl, wobei der Heterocyclyl-Rest des letztgenannten Substituenten partiell oder vollständig halogeniert sein kann und/ oder einen bis drei der folgenden Reste tragen kann: Nitro, Cyano, Cx^-Alkyl, C1-C4 -Halogenalkyl, C1-C4 -Alkoxy oder C1-C4 -Halogenalkoxy; R13 Cι-C6-Alkyl, C3-C6-Alkenyl, C3-C6-Halogenalkenyl,R 20 is hydroxy, mercapto, halogen, OR 13 , SR 13 , S0 2 R 14 , OS0 2 R 14 , NR 17 R 18 , ONR 18 R 19 or N-linked heterocyclyl, the heterocyclyl radical of the latter substituent being partially or completely can be halogenated and / or can carry one to three of the following radicals: nitro, cyano, Cx ^ alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy; R 13 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl,
C3-C6-Alkinyl, Cι-C6-Alkylcarbonyl, C3-C6-Cycloalkyl- carbonyl, Cι-C6-Alkylaminocarbonyl, N,N-Di- (Cι-C6-al- kyl) oder Cι-C6-Alkylcarbonyl-Cι-C6-alkyl, wobei die genannten Alkyl- oder Cycloalkylreste partiell oder vollständig halogeniert sein können und/oder eine bis drei der folgenden Gruppen tragen können: Cyano, C!-C4-Alkoxy, Cι-C -Alkylthio, C!-C4-Alkyl- carbonyl, C1-C4-Alkoxycarbonyl, Hydroxycarbonyl , Di- (Cι-C4-alkyl) -aminocarbonyl, Cι-C4-Alkylcarbonyloxy oder C3-C6-Cycloalkyl;C 3 -C 6 alkynyl, -C-C 6 alkylcarbonyl, C 3 -C 6 -cycloalkylcarbonyl, Cι-C 6 -alkylaminocarbonyl, N, N-di- (Cι-C 6 -alkyl) or Cι -C 6 -Alkylcarbonyl -CC-C 6 -alkyl, where the alkyl or cycloalkyl radicals mentioned can be partially or completely halogenated and / or can carry one to three of the following groups: cyano, C ! -C 4 -alkoxy, -C-C -alkylthio, C ! -C 4 alkyl carbonyl, C 1 -C 4 -alkoxycarbonyl, hydroxycarbonyl, di- (Cι-C4 alkyl) aminocarbonyl, Cι-C 4 alkylcarbonyloxy or C 3 -C 6 cycloalkyl;
Phenyl, Heterocyclyl, Phenyl-Ci-Cβ-alkyl, Heterocy- clyl-Cι-C6-alkyl, Phenylcarbonyl oder Heterocyclylcar- bonyl, wobei der Phenyl- und der Heterocyclyl-Rest derPhenyl, heterocyclyl, phenyl-C 1 -C 6 -alkyl, heterocyclyl-C 1 -C 6 -alkyl, phenylcarbonyl or heterocyclylcarbonyl, the phenyl and heterocyclyl radicals being the
6 letztgenannten Substituenten partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann: Nitro, Cyano, C1-C4-Alkyl, Cχ-C4-Halogenalkyl, Cι~C4-Alkoxy oder Cι-C4-Halogenalkoxy;6 latter substituents can be partially or completely halogenated and / or can carry one to three of the following radicals: nitro, cyano, C 1 -C 4 alkyl, Cχ-C 4 haloalkyl, -C ~ C 4 alkoxy or Cι-C 4 -haloalkoxy;
R14 Cι-C6-Alkyl, C3-C6-Alkenyl , C3-C6-Halogenalkenyl,R 14 -CC 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl,
C3-C6-Cycloalkyl, Hydroxy, Cι-C6-Alkoxy, Di- (Cι-C6-al - kyDamino oder Di- (Ci-Cβ-halogenalkyl) amino, wobei die genannten Alkyl-, Cycloalkyl- und Alkoxyreste partiell oder vollständig halogeniert sein können und/oder eine bis drei der folgenden Gruppen tragen können: Cyano, Cι-C -Alkoxy, Cι-C4-Alkylthio, Cι-C4-Alkyl- carbonyl oder Cι-C4-Alkoxycarbonyl;C 3 -C 6 cycloalkyl, hydroxy, -C-C 6 alkoxy, di- (-C-C 6 -al - kyDamino or di- (Ci-Cβ-haloalkyl) amino, the said alkyl, cycloalkyl and alkoxy radicals can be partially or completely halogenated and / or can carry one to three of the following groups: cyano, -C-alkoxy, -C-C 4 -alkylthio, -C-C 4 -alkylcarbonyl or -C-C 4 -alkoxycarbonyl;
Phenyl, Heterocyclyl, Phenoxy oder Heterocyclyloxy, wobei der Phenyl- und der Heterocyclyl-Rest der letztgenannten Substituenten partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann:Phenyl, heterocyclyl, phenoxy or heterocyclyloxy, where the phenyl and heterocyclyl radicals of the latter substituents can be partially or completely halogenated and / or can carry one to three of the following radicals:
Nitro, Cyano, Cι-C4-Alkyl, Cι-C4-Halogenalkyl, Cι-C4-Alkoxy oder Cι-C4-Halogenalkoxy;Nitro, cyano, C 4 -alkyl, C 4 haloalkyl, Cι-C 4 alkoxy or Cι-C 4 haloalkoxy;
R17 Cι-C6 -Alkyl, C3-C6 -Alkenyl, C3 -C6-Halogenalkenyl, C3-C6 -Cycloalkyl, Cι-C6-Alkoxy oder C3-C6-Alkenyloxy, wobei die genannten Alkyl-, Cycloalkyl- und Alkoxyreste partiell oder vollständig halogeniert sein können und/ oder einen bis drei Reste der folgenden Gruppe tragen können: Cyano, C1-C4 -Alkoxy oder C1-C4 -Aikylthio; Phenyl, Heterocyclyl, Phenyl -Cι-C6-alkyl oder Hetero - cyclyl-Cι-C6-alkyl, wobei der Phenyl- oder Heterocyclyl-Rest der vier letztgenannten Substituenten partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann:R 17 Cι-C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 cycloalkyl, Cι-C 6 alkoxy or C 3 -C 6 alkenyloxy, wherein the said alkyl, cycloalkyl and alkoxy radicals can be partially or completely halogenated and / or can carry one to three radicals from the following group: cyano, C 1 -C 4 alkoxy or C 1 -C 4 alkylthio; Phenyl, heterocyclyl, phenyl -C -C 6 alkyl or hetero - cyclyl -C -C 6 alkyl, where the phenyl or heterocyclyl radical of the four last-mentioned substituents can be partially or completely halogenated and / or one to three of the following Can carry leftovers:
Nitro, Cyano, C1-C4 -Alkyl, C1-C4-Halogenalkyl, C1-C4 -Alkoxy oder C1-C4 -Halogenalkoxy;Nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 -haloalkoxy;
R18, R19 Cι-C6 -Alkyl oder C3 -C6 -Alkenyl;R 18 , R 19 -CC 6 alkyl or C 3 -C 6 alkenyl;
R21 Cι-C6 -Alkyl, wie Methyl, Ethyl, 1-Methyl-eth-l-yl, oder 1 , 1 -Dimethyl -eth- 1 -yl ;R 21 -C 6 -alkyl, such as methyl, ethyl, 1-methyl-eth-l-yl, or 1, 1-dimethyl-eth-1 -yl;
R22 Wasserstoff oder Cι-C6 -Alkyl wie Methyl oder Ethyl; insbesondere Wasserstoff oder Methyl;R 22 is hydrogen or -CC 6 alkyl such as methyl or ethyl; especially hydrogen or methyl;
Außerordentlich bevorzugt sind die Verbindungen Ib, wobei die Variablen folgende Bedeutung haben:The compounds Ib are extremely preferred, the variables having the following meaning:
R20 Hydroxy.R 20 hydroxy.
Ebenso bevorzugt sind Verbindungen der Formel Ic, insbesonders die Verbindungen lc, wobei die Variablen folgende Bedeutung haben:Likewise preferred are compounds of the formula Ic, in particular the compounds 1c, the variables having the following meaning:
R23 Cι-C6 -Alkyl oder C3-C6 -Cycloalkyl; insbesondere Cyclopropyl;R 23 -C 6 alkyl or C 3 -C 6 cycloalkyl; especially cyclopropyl;
R24 Wasserstoff;R 24 is hydrogen;
Ebenso bevorzugt sind Verbindungen der Formel Id, insbesonders die Verbindungen ld, wobei die Variablen folgende Bedeutung haben:Likewise preferred are compounds of the formula Id, in particular the compounds id, where the variables have the following meaning:
R25 Cι-C6-Alkyl oder C3-C6 -Cycloalkyl;R 25 -CC 6 alkyl or C 3 -C 6 cycloalkyl;
Weiterhin bevorzugt sind die Verbindungen II (= I mit X=0, R3 in 4-Position, R4 in 5-Position und "P(=X)R1R2" in 2-Position gebunden) The compounds II (= I with X = 0, R 3 in the 4-position, R 4 in the 5-position and "P (= X) R 1 R 2 " in the 2-position are furthermore preferably bonded)
Im Hinblick auf die Variablen R1 bis R4 und Q gelten die voranste henden Ausführungen.With regard to the variables R 1 to R 4 and Q, the above explanations apply.
Insbesondere bevorzugt sind die Verbindungen II, wobei die Variablen folgende Bedeutung haben:Compounds II are particularly preferred, the variables having the following meaning:
R3 Nitro, Cyano, Halogen, Cι-C4-Alkyl, C!-C4 -Halogenalkyl, Ci-Cδ-Alkoxy, C1-C4 -Halogenalkoxy, C1-C4 -Alkylsulfonyl oder C1-C4 -Halogenalkylsulfonyl;R 3 nitro, cyano, halogen, -CC 4 alkyl, C ! -C 4 haloalkyl, Ci-Cδ alkoxy, C 1 -C4 haloalkoxy, C 1 -C 4 alkylsulfonyl or C1-C4 haloalkylsulfonyl;
R4 Halogen, wie Chlor oder Brom, oder C3.-C4 -Alkyl wie Methyl oder Ethyl;R 4 is halogen, such as chlorine or bromine, or C 3 -C 4 -alkyl, such as methyl or ethyl;
1 0 oder 1;1 0 or 1;
Ebenso weiterhin bevorzugt sind die Verbindungen 12 (≡ I mit X=0, R3 in 2 -Position, R4 in 5 -Position und "Pf^XjRiR2" in 4 -Position gebunden)Likewise further preferred are the compounds 12 (≡ I with X = 0, R 3 in the 2 position, R 4 in the 5 position and "Pf ^ XjRiR 2 " in the 4 position)
Im Hinblick auf die Variablen R1 bis R4 und Q gelten die voranstellenden Ausführungen.With regard to the variables R 1 to R 4 and Q, the explanations above apply.
Insbesondere bevorzugt sind die Verbindungen 12, wobei die Variablen folgende Bedeutung haben: R3 Nitro, Cyano, Halogen, C1-C4 -Alkyl, C1-C4 -Halogenalkyl , Cι-C -Alkoxy, C1-C4 -Halogenalkoxy, Cι-C4-Alkylthio, Cι-C4-Halogenalkylthio, C1-C4 -Alkylsulfonyl oder C1-C4 -Halogenalkylsulfonyl;The compounds 12 are particularly preferred, the variables having the following meaning: R 3 is nitro, cyano, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, Cι-C alkoxy, C 1 -C 4 haloalkoxy, Cι-C 4 alkylthio, Cι-C 4 - Haloalkylthio, C 1 -C 4 alkylsulfonyl or C 1 -C 4 haloalkylsulfonyl;
R4 Halogen, wie Chlor oder Brom, oder C1-C4 -Alkyl wie Methyl oder Ethyl;R 4 halogen, such as chlorine or bromine, or C 1 -C 4 alkyl such as methyl or ethyl;
1 0 oder 1;1 0 or 1;
Ebenso weiterhin bevorzugt sind die Verbindungen I, insbesonders die Verbindungen la, Ib, II oder 12, wobei die Variablen folgende Bedeutung haben:Also preferred are the compounds I, in particular the compounds Ia, Ib, II or 12, where the variables have the following meaning:
R^R2 Wasserstoff, Cι-C6-Alkyl, Hydroxy oder Cι-C6-Alkoxy, wobei die Alkylreste der 3 letztgenannten Substituenten partiell oder vollständig halogeniert sein können und/ oder eine bis drei der folgenden Gruppen tragen können: Nitro, Cyano, Cι-C4-Alkoxy, C1-C -Alkylsulfonyl oder C1-C4 -Alkoxycarbonyl; insbesonders bevorzugt Wasserstoff, C1-C4 -Alkyl oder Ci -C4-Alkoxy;R ^ R 2 is hydrogen, -CC 6 alkyl, hydroxy or -CC 6 alkoxy, where the alkyl radicals of the latter 3 substituents can be partially or completely halogenated and / or can carry one to three of the following groups: nitro, cyano , -CC 4 alkoxy, C 1 -C alkylsulfonyl or C 1 -C 4 alkoxycarbonyl; particularly preferably hydrogen, C 1 -C 4 alkyl or Ci -C 4 alkoxy;
Ebenso weiterhin bevorzugt sind die Verbindungen Ila ( = I mit X=0, R3 in 4 -Position, Rι in 5-Position und "P^XjRiR2" in Position gebunden und Q=Q1) .Also preferred are the compounds Ila (= I with X = 0, R 3 in the 4-position, Rι in the 5-position and "P ^ XjR i R 2 " in position and Q = Q 1 ).
Insbesonders bevorzugt sind die Verbindungen Ila ( = I mit X=0, R3 in 4-Position, R4ι in 5-Position und "P(=X)R1R2" in 2-Position), wobei die Variablen folgende Bedeutung haben:The compounds Ila (= I with X = 0, R 3 in the 4-position, R 4 ι in the 5-position and "P (= X) R 1 R 2 " in the 2-position) are particularly preferred, the variables being as follows Have meaning:
R^R2 Cι-C4 -Alkyl oder Ci -C4-Alkoxy; insbesondere Ci -C4-Alkyl;R ^ R 2 -CC 4 alkyl or Ci -C 4 alkoxy; in particular Ci -C 4 alkyl;
R3 Halogen;R 3 halogen;
1 O;1 O;
R6 Hydroxy;R 6 hydroxy;
R7,R8,R9,R10,R1:L,R12 Wasserstoff oder C1-C4 -Alkyl,R 7 , R 8 , R 9 , R 10 , R 1: L , R 12 are hydrogen or C 1 -C 4 alkyl,
oder R9 und R10 bilden gemeinsam mit dem Kohlenstoff an den sie gebunden sind eine Carbonylgruppe aus; Ebenso weiterhin bevorzugt sind die Verbindungen I2a (≡ I mit X=0, R3 in 2-Position, Rχ in 5-Position und "P(=X)R1R2" in 4-Po- sition gebunden und Q=Q1) .or R 9 and R 10 together with the carbon to which they are attached form a carbonyl group; Likewise further preferred are the compounds I2a (≡ I with X = 0, R 3 in the 2-position, R 5 in the 5-position and "P (= X) R 1 R 2 " in the 4-position and Q = Q 1 ).
Insbesondere bevorzugt sind die Verbindungen I2a (= I mit X=0, R3 in 2-Position, R4χ in 5-Position und "P(=X)R1R2" in 4-Position gebunden und Q=QX) , wobei die Variablen folgende Bedeutung haben:The compounds I2a (= I with X = 0, R 3 in the 2-position, R 4 χ in the 5-position and "P (= X) R 1 R 2 " in the 4-position and Q = Q X ), where the variables have the following meaning:
R!,R2 C3.-C4 -Alkyl oder Ci -C -Alkoxy;R !, R 2 C 3 -C 4 alkyl or Ci -C alkoxy;
R3 Halogen;R 3 halogen;
1 0;1 0;
R6 Hydroxy oder Phenylthio, wobei der Phenylrest partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann: Nitro, Cyano, Cχ-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4 -Alkoxy oder C1-C4 -Halogenalkoxy;R 6 is hydroxy or phenylthio, where the phenyl radical can be partially or completely halogenated and / or can carry one to three of the following radicals: nitro, cyano, Cχ-C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy;
R^R^R^R10^11^12 Wasserstoff oder C1-C -Alkyl;R ^ R ^ R ^ R 10 ^ 11 ^ 12 is hydrogen or C 1 -C alkyl;
oder R9 und R10 bilden gemeinsam mit dem Kohlenstoff an den sie gebunden sind eine Carbonylgruppe aus;or R 9 and R 10 together with the carbon to which they are attached form a carbonyl group;
oder R7 und R11 bilden gemeinsam eine - (CH2) - oder - (CH2) 2-Kette, insbesonders eine - (CH ) 2 -Kette aus.or R 7 and R 11 together form a - (CH 2 ) - or - (CH 2 ) 2 chain, in particular a - (CH) 2 chain.
Ebenso weiterhin bevorzugt sind die Verbindungen I2b (≡ I mit X=0, R3 in 2-Position, R4χ in 5-Position und "P(=X)R1R2" in 4 -Position) .Also preferred are the compounds I2b (≡ I with X = 0, R 3 in the 2 position, R 4 χ in the 5 position and "P (= X) R 1 R 2 " in the 4 position).
Insbesondere bevorzugt sind die Verbindungen I2b (≡ I mit X=0, R3 in 2-Position, R4χ in 5-Position und "P(=X)R1R2" in 4-Position), wobei die Variablen folgende Bedeutung haben:The compounds I2b (≡ I with X = 0, R 3 in the 2-position, R 4 χ in the 5-position and "P (= X) R 1 R 2 " in the 4-position) are particularly preferred, the variables being as follows Have meaning:
RX,R2 C1-C4 -Alkyl oder Ci -C -Alkoxy; insbesondere Ci-C4-Alkoxy;R X , R 2 C 1 -C 4 alkyl or Ci -C alkoxy; in particular Ci-C 4 alkoxy;
R3 Halogen;R 3 halogen;
1 0;1 0;
R20 Hydroxy; R21 Ci - C4 - Alkyl ;R 20 hydroxy; R 21 Ci - C 4 alkyl;
R22 Wasserstoff oder Cx-C4-Alkyl; insbesondere Wasserstof .R 22 is hydrogen or C x -C 4 alkyl; especially hydrogen.
Außerordentlich bevorzugt sind die Verbindungen Ilal (≡ I mit X=0, R3 in 4-Position, R4 in 5-Position und "P(=X)R1R2" in 2-Posi- tion gebunden, Q=Q1, R7 bis R12 = Wasserstoff), insbesondere die Verbindungen Ilal.n, wobei die Variablen R1 bis R4 und R6 die in der Tabelle 1 genannte Bedeutung haben.The compounds Ilal (≡ I with X = 0, R 3 in the 4-position, R 4 in the 5-position and "P (= X) R 1 R 2 " in the 2-position are particularly preferably bound, Q = Q 1 , R 7 to R 12 = hydrogen), in particular the compounds Ilal.n, where the variables R 1 to R 4 and R 6 have the meaning given in Table 1.
Die gegebenen Restedefinitionen X, R1 bis R12, Q und 1 sind nicht nur in Kombination miteinander, sondern auch jeweils für sich al- lein betrachtet für die erfindungsgemäßen Verbindungen von bevorzugter Bedeutung. The given radical definitions X, R 1 to R 12 , Q and 1 are not only preferred in combination with one another, but also in each case are of particular importance when considered individually for the compounds according to the invention.
Tabelle 1Table 1
wöbei : wöbei:
Hetl für 1-Methoxy-N-methylamino; Het2 für 1-Tetrahydropyrrolyl; Het3 für 1-Tetrahydroisoxazolyl; stehen Ebenso außerordentlich bevorzugt sind die Verbindungen Ila2 (== I mit X = 0; R3 in 4 -Position, R4 in 5-Position und „P(=X)R1R2" in 2-Position gebunden; Q = Q1; R7, R8, R9, R11, R12 = H und R10 = CH3) , insbesondere die Verbindungen Ila2.n, wobei die Variablen R1 bis R4 und R6 die in Tabelle 1 genannte Bedeutung haben.Hetl for 1-methoxy-N-methylamino; Het2 for 1-tetrahydropyrrolyl; Het3 for 1-tetrahydroisoxazolyl; stand The compounds Ila2 (== I with X = 0; R 3 in the 4-position, R 4 in the 5-position and “P (= X) R 1 R 2 ” in the 2-position are also extremely preferably bound; Q = Q 1 ; R 7 , R 8 , R 9 , R 11 , R 12 = H and R 10 = CH 3 ), in particular the compounds Ila2.n, where the variables R 1 to R 4 and R 6 have the meaning given in Table 1 to have.
Ebenso außerordentlich bevorzugt sind die Verbindungen Ila3 (= I mit X = 0; R3 in 4-Position, R4 in 5-Position und „P(=X)R1R2" in 2 -Position gebunden; Q = Q1; R8, R9, R10, R11, R12 = H und R7 = CH3) , insbesondere die Verbindungen Ila3.n, wobei die Variablen R1 bis R4 und R6 die in Tabelle 1 genannte Bedeutung haben.The compounds Ila3 (= I with X = 0; R 3 in the 4-position, R 4 in the 5-position and "P (= X) R 1 R 2 " in the 2-position are also particularly preferably bound; Q = Q 1 R 8 , R 9 , R 10 , R 11 , R 12 = H and R 7 = CH 3 ), in particular the compounds Ila3.n, where the variables R 1 to R 4 and R 6 have the meaning given in Table 1 .
Ebenso außerordentlich bevorzugt sind die Verbindungen Ila4 (Ξ≡ I mit X = 0; R3 in 4-Position, R4 in 5-Position und „P(=X)R1R2" in 2 -Position gebunden; Q = Ql; R7, R8, R11, R2 = H und R9, R10 = CH3) , insbesondere die Verbindungen Ila4.n, wobei die Variablen R1 bis R4 und R6 die in Tabelle 1 genannte Bedeutung haben.The compounds Ila4 (Ξ≡ I with X = 0; R 3 in the 4-position, R 4 in the 5-position and "P (= X) R 1 R 2 " in the 2-position are also extremely preferably bound; Q = Ql R 7 , R 8 , R 11 , R 2 = H and R 9 , R 10 = CH 3 ), in particular the compounds Ila4.n, where the variables R 1 to R 4 and R 6 have the meaning given in Table 1 .
Ebenso außerordentlich bevorzugt sind die Verbindungen Ila5 (≡ I mit X = 0; R3 in 4-Position, R4 in 5-Position und „P(=X)R1R2" in 2-Position gebunden; Q = Q1; R7, R8 = CH3 und R9, R10, R11, R12 = H) , insbesondere die Verbindungen Ila5.n, wobei die Variablen R1 bis R4 und R6 die in Tabelle 1 genannte Bedeutung haben. The compounds Ila5 (≡ I with X = 0; R 3 in the 4-position, R 4 in the 5-position and “P (= X) R 1 R 2 ” in the 2-position are also extremely preferred; Q = Q 1 R 7 , R 8 = CH 3 and R 9 , R 10 , R 11 , R 12 = H), in particular the compounds Ila5.n, where the variables R 1 to R 4 and R 6 have the meaning given in Table 1 .
Ebenso außerordentlich bevorzugt sind die Verbindungen Ila6 (≡ I mit X = 0; R3 in 4 -Position, R4 in 5 -Position und „P(=X)R1R2" in 2 -Position gebunden; Q = Q1; R7, R8, R9, R10 = H und R11, R12 = CH3) , insbesondere die Verbindungen Ila6.n, wobei die Variablen R1 bis R4 und R6 die in Tabelle 1 genannte Bedeutung haben.Likewise, the compounds Ila6 (≡ I with X = 0; R 3 in the 4 position, R 4 in the 5 position and "P (= X) R 1 R 2 " in the 2 position are bonded with particular preference; Q = Q 1 R 7 , R 8 , R 9 , R 10 = H and R 11 , R 12 = CH 3 ), in particular the compounds Ila6.n, where the variables R 1 to R 4 and R 6 have the meaning given in Table 1 .
Ebenso außerordentlich bevorzugt sind die Verbindungen Ila7 (≡ I mit X = O; R3 in 4 -Position, R4 in 5 -Position und „P(=X)R1R2" in 2 -Position gebunden; Q = Q1; R7, R8, R11, R12 = H und R9 und R10 bilden gemeinsam mit dem Kohlenstoff, an dem sie gebunden sind eine Carbonylgruppe aus), insbesondere die Verbindungen Ila7.n, wobei die Variablen R1 bis R4 und R6 die in Tabelle 1 genannte Bedeutung haben.The compounds Ila7 (≡ I with X = O; R 3 in the 4 position, R 4 in the 5 position and “P (= X) R 1 R 2 ” in the 2 position are also particularly preferably bound; Q = Q 1 R 7 , R 8 , R 11 , R 12 = H and R 9 and R 10 together with the carbon to which they are attached form a carbonyl group), in particular the compounds Ila7.n, where the variables R 1 to R 4 and R 6 have the meaning given in Table 1.
Ebenso außerordentlich bevorzugt sind die Verbindungen Ila8 (= I mit X = 0; R3 in 4 -Position, R4 in 5-Position und „P(=X)R1R2" in 2 -Position gebunden; Q = Q1; R7, R8, R11, R12 = CH3 und R9 und R10 bilden gemeinsam mit dem Kohlenstoff, an dem sie gebunden sind eine Carbonylgruppe aus), insbesondere die Verbindungen Ilaδ.n, wobei die Variablen R1 bis R4 und R6 die in Tabelle 1 genannte Bedeutung haben. The compounds Ila8 (= I with X = 0; R 3 in the 4-position, R 4 in the 5-position and "P (= X) R 1 R 2 " in the 2-position are also particularly preferably bound; Q = Q 1 R 7 , R 8 , R 11 , R 12 = CH 3 and R 9 and R 10 together with the carbon to which they are attached form a carbonyl group), in particular the compounds Ilaδ.n, where the variables R 1 to R 4 and R 6 have the meaning given in Table 1.
Ebenso außerordentlich bevorzugt sind die Verbindungen Ila9 (-= I mit X = 0; R3 in 4 -Position, R4 in 5-Position und „P(=X)R1R2" in 2 -Position gebunden; Q = Q1; R7 und R11 bilden gemeinsam eineThe compounds Ila9 (- = I with X = 0; R 3 in the 4-position, R 4 in the 5-position and "P (= X) R 1 R 2 " in the 2-position are also extremely preferred; Q = Q 1 ; R 7 and R 11 together form one
-CH2-CH2 -Kette aus und R8, R9, R10, R12 = H) , insbesondere die Verbindungen Ila9.n, wobei die Variablen R1 bis R4 und R6 die in Tabelle 1 genannte Bedeutung haben.-CH 2 -CH 2 chain from and R 8 , R 9 , R 10 , R 12 = H), in particular the compounds Ila9.n, where the variables R 1 to R 4 and R 6 have the meaning given in Table 1 .
Ebenso außerordentlich bevorzugt sind die Verbindungen I2al (Ξ≡ I mit X = 0; R3 in 2 -Position, R4 in 5-Position und „P(=X)R1R2" in 4-Position gebunden; Q = Q1; R7 , R8, R9 , R10, R11, R12 = H) , insbesondere die Verbindungen I2al.n, wobei die Variablen R1 bis R4 und R6 die in Tabelle 1 genannte Bedeutung haben.The compounds I2al (Ξ≡ I with X = 0; R 3 in the 2-position, R 4 in the 5-position and "P (= X) R 1 R 2 " in the 4-position are also extremely preferred; Q = Q 1 ; R 7 , R 8 , R 9 , R 10 , R 11 , R 12 = H), in particular the compounds I2al.n, where the variables R 1 to R 4 and R 6 have the meaning given in Table 1.
Ebenso außerordentlich bevorzugt sind die Verbindungen I2a2 (≡ I mit X = 0; R3 in 2 -Position, R4 in 5 -Position und „P(=X)R1R2" in 4-Position gebunden; Q = Q1; R7, R8, R9, R11, R12 = H und R10 = CH3) , insbesondere die Verbindungen I2a2.n, wobei die Variablen R1 bis R4 und R6 die in Tabelle 1 genannte Bedeutung haben. The compounds I2a2 (≡ I with X = 0; R 3 in the 2 position, R 4 in the 5 position and “P (= X) R 1 R 2 ” in the 4 position are also extremely preferred; Q = Q 1 R 7 , R 8 , R 9 , R 11 , R 12 = H and R 10 = CH 3 ), in particular the compounds I2a2.n, where the variables R 1 to R 4 and R 6 have the meaning given in Table 1 .
Ebenso außerordentlich bevorzugt sind die Verbindungen I2a3 (Ξ≡ I mit X = 0; R3 in 2 -Position, R4 in 5-Position und „P(=X)R1R2" in 4 -Position gebunden; Q = Q1; R8, R9, R10, R11, R12 = H und R7 = CH3) , insbesondere die Verbindungen I2a3.n, wobei die Variablen R1 bis R4 und R6 die in Tabelle 1 genannte Bedeutung haben.The compounds I2a3 (Ξ≡ I with X = 0; R 3 in the 2-position, R 4 in the 5-position and “P (= X) R 1 R 2 ” in the 4-position are also extremely preferred; Q = Q 1 ; R 8 , R 9 , R 10 , R 11 , R 12 = H and R 7 = CH 3 ), in particular the compounds I2a3.n, where the variables R 1 to R 4 and R 6 have the meaning given in Table 1 to have.
Ebenso außerordentlich bevorzugt sind die Verbindungen I2a4 (Ξ≡ I mit X = 0; R3 in 2 -Position, R4 in 5-Position und „P(=X)R1R2" in 4 -Position gebunden; Q = Q1; R7, R8, R11, R12 = H und R9, R10 = CH3) , insbesondere die Verbindungen I2a4.n, wobei die Variablen R1 bis R4 und R6 die in Tabelle 1 genannte Bedeutung haben.The compounds I2a4 (Ξ≡ I with X = 0; R 3 in the 2-position, R 4 in the 5-position and “P (= X) R 1 R 2 ” in the 4-position are also extremely preferred; Q = Q 1 ; R 7 , R 8 , R 11 , R 12 = H and R 9 , R 10 = CH 3 ), in particular the compounds I2a4.n, where the variables R 1 to R 4 and R 6 have the meaning given in Table 1 to have.
Ebenso außerordentlich bevorzugt sind die Verbindungen I2a5 (= I mit X = 0; R3 in 2 -Position, R4 in 5-Position und „P(=X)R1R2" in 4-Position gebunden; Q = Q1; R7, R8 = CH3, R9, R10, R11, R12 = H) , insbesondere die Verbindungen I2a5.n, wobei die Variablen R1 bis R4 und R6 die in Tabelle 1 genannte Bedeutung haben.The compounds I2a5 (= I with X = 0; R 3 in the 2-position, R 4 in the 5-position and “P (= X) R 1 R 2 ” in the 4-position are also extremely preferred; Q = Q 1 ; R 7 , R 8 = CH 3 , R 9 , R 10 , R 11 , R 12 = H), in particular the compounds I2a5.n, where the variables R 1 to R 4 and R 6 have the meaning given in Table 1.
Ebenso außerordentlich bevorzugt sind die Verbindungen I2a6 (== I mit X = O; R3 in 2-Position, R4 in 5-Position und „P(=X)R1R2" in 4 -Position gebunden; Q = Q1; R7, R8, R9, R10 = H und R11, R12 = CH3) , insbesondere die Verbindungen I2a6.n, wobei die Variablen R1 bis R4 und R6 die in Tabelle 1 genannte Bedeutung haben.The compounds I2a6 (== I with X = O; R 3 in the 2-position, R 4 in the 5-position and “P (= X) R 1 R 2 ” in the 4-position are also extremely preferred; Q = Q 1 ; R 7 , R 8 , R 9 , R 10 = H and R 11 , R 12 = CH 3 ), in particular the compounds I2a6.n, where the variables R 1 to R 4 and R 6 have the meaning given in Table 1 to have.
Ebenso außerordentlich bevorzugt sind die Verbindungen I2a7 (ΞΞΞ≡ I mit X = 0; R3 in 2-Position, R4 in 5-Position und „P(=X)R1R2" in 4-Position gebunden; Q = Q1; R7, R8, R11, R12 = H und R9 und R10 bilden gemeinsam mit dem Kohlenstoff, an dem sie gebunden sind eine Carbonylgruppe aus), insbesondere die Verbindungen I2a7.n, wobei die Variablen R1 bis R4 und R6 die in Tabelle 1 genannte Bedeutung haben.The compounds I2a7 (ΞΞΞ≡ I with X = 0; R 3 in the 2-position, R 4 in the 5-position and “P (= X) R 1 R 2 ” in the 4-position are also extremely preferred; Q = Q 1 ; R 7 , R 8 , R 11 , R 12 = H and R 9 and R 10 together with the carbon to which they are attached form a carbonyl group), in particular the compounds I2a7.n, where the variables R 1 to R 4 and R 6 have the meaning given in Table 1.
Ebenso außerordentlich bevorzugt sind die Verbindungen I2a8 (= I mit X = 0; R3 in 2 -Position, R4 in 5 -Position und „P(=X)R1R2" in 4 -Position gebunden; Q = Q1; R7, R8, R11, R12 = CH3 und R9 und R10 bilden gemeinsam mit dem Kohlenstoff, an dem sie gebunden sind eine Carbonylgruppe aus), insbesondere die Verbindungen I2a8.n, wobei die Variablen R1 bis R4 und R6 die in Tabelle 1 genannte Be deutung haben.Likewise, the compounds I2a8 (= I with X = 0; R 3 in the 2 position, R 4 in the 5 position and “P (= X) R 1 R 2 ” in the 4 position are bonded with particular preference; Q = Q 1 R 7 , R 8 , R 11 , R 12 = CH 3 and R 9 and R 10 together with the carbon to which they are attached form a carbonyl group), in particular the compounds I2a8.n, where the variables R 1 to R 4 and R 6 have the meaning given in Table 1 Be.
Ebenso außerordentlich bevorzugt sind die Verbindungen I2a9 (≡ I mit X = 0; R3 in 2 -Position, R4 in 5-Position und „P(=X)R1R2" in 4 -Position gebunden; Q = Q1; R7 und R11 bilden gemeinsam eine -CH2-CH2 -Kette aus und R8, R9, R10, R12 = H) , insbesondere die Verbindungen I2a9.n, wobei die Variablen R1 bis R4 und R6 die in Tabelle 1 genannte Bedeutung haben.The compounds I2a9 (≡ I with X = 0; R 3 in the 2-position, R 4 in the 5-position and "P (= X) R 1 R 2 " in the 4-position are also extremely preferred; Q = Q 1 R 7 and R 11 together form a -CH 2 -CH 2 chain and R 8 , R 9 , R 10 , R 12 = H), in particular the compounds I2a9.n, where the variables R 1 to R 4 and R 6 have the meaning given in Table 1.
Ebenso außerordentlich bevorzugt sind die Verbindungen Ilbl (== I mit X = 0; R3 in 4 -Position, R4 in 5 -Position und „P(=X)R1R2" in 2-Position gebunden; Q = Q2; R2l = CH3 und R2 = H) , insbesondere die Verbindungen Ilbl.n, wobei die Variablen R1 bis R4 und R20 The compounds Ilbl (== I with X = 0; R 3 in the 4-position, R 4 in the 5-position and “P (= X) R 1 R 2 ” in the 2-position are also extremely preferred; Q = Q 2 ; R2l = CH 3 and R 2 = H), in particular the compounds Ilbl.n, where the variables R 1 to R 4 and R 20
(entspricht in diesem Fall R6) die in Tabelle 1 genannte Bedeutung haben.(corresponds to R 6 in this case) have the meaning given in Table 1.
Ebenso außerordentlich bevorzugt sind die Verbindungen Ilb2 (= I mit X = 0; R3 in 4-Position, R4 in 5-Position und „P(=X)R1R2" in 2-Position gebunden; Q = Q2 ; R21 = CH2CH3 und R2 = H) , insbesondere die Verbindungen Ilb2.n, wobei die Variablen R1 bis R4 und R20 (entspricht in diesem Fall R6) die in Tabelle 1 genannte Bedeutung haben.The compounds Ilb2 (= I with X = 0; R 3 in the 4-position, R 4 in the 5-position and "P (= X) R 1 R 2 " in the 2-position are also extremely preferably bound; Q = Q 2 ; R 21 = CH 2 CH 3 and R 2 = H), in particular the compounds Ilb2.n, where the variables R 1 to R 4 and R 20 (in this case corresponds to R 6 ) have the meaning given in Table 1.
Ebenso außerordentlich bevorzugt sind die Verbindungen Ilb3 (≡ I mit X = 0; R3 in 4-Position, R4 in 5-Position und „P(=X)R1R2" in 2-Position gebunden; Q = Q2; R21 = CH(CH3)2 und R22 = H) , insbesondere die Verbindungen Ilb3.n, wobei die Variablen R1 bis R4 und R20 (entspricht in diesem Fall R6) die in Tabelle 1 genannte Bedeutung haben.The compounds Ilb3 (≡ I with X = 0; R 3 in the 4-position, R 4 in the 5-position and "P (= X) R 1 R 2 " in the 2-position are also extremely preferred; Q = Q 2 R 21 = CH (CH 3 ) 2 and R 22 = H), in particular the compounds Ilb3.n, where the variables R 1 to R 4 and R 20 (in this case corresponds to R 6 ) have the meaning given in Table 1 .
Ebenso außerordentlich bevorzugt sind die Verbindungen Ilb4 (= I mit X = 0; R3 in 4 -Position, R4 in 5-Position und „P(=X)R1R2" in 2-Position gebunden; Q = Q2 ; R2 = c(CH3)3 und R22 = H) , insbesondere die Verbindungen Ilb4.n, wobei die Variablen R1 bis R4 und R20 (entspricht in diesem Fall R6) die in Tabelle 1 genannte Bedeutung haben.The compounds Ilb4 (= I with X = 0; R 3 in the 4-position, R 4 in the 5-position and "P (= X) R 1 R 2 " in the 2-position are also particularly preferably bound; Q = Q 2 ; R 2 = c (CH 3 ) 3 and R 22 = H), in particular the compounds Ilb4.n, where the variables R 1 to R 4 and R 20 (in this case corresponds to R 6 ) have the meaning given in Table 1 .
Ebenso außerordentlich bevorzugt sind die Verbindungen Ilb5 (Ξ≡ I mit X = 0; R3 in 4 -Position, R4 in 5 -Position und „P(=X)R1R2" in 2-Position gebunden; Q = Q2; R21 = CH2CF3 und R22 = H) , insbeson- dere die Verbindungen Ilb5.n, wobei die Variablen R1 bis R4 und R20 (entspricht in diesem Fall R6) die in Tabelle 1 genannte Bedeutung haben.The compounds Ilb5 (Ξ≡ I with X = 0; R 3 in the 4-position, R 4 in the 5-position and “P (= X) R 1 R 2 ” in the 2-position are also particularly preferred; Q = Q 2 ; R 21 = CH 2 CF 3 and R 22 = H), in particular the compounds Ilb5.n, where the variables R 1 to R 4 and R 20 (in this case corresponds to R 6 ) have the meaning given in Table 1.
Ebenso außerordentlich bevorzugt sind die Verbindungen Ilb6 (≡≡ I mit X = 0; R3 in 4 -Position, R4 in 5 -Position und „P(=X)R1R2" in 2-Position gebunden; Q = Q2,- R21 = CH3 und R2 = CH3) , insbesondere die Verbindungen Ilb6.n, wobei die Variablen R1 bis R4 und R20 (entspricht in diesem Fall R6) die in Tabelle 1 genannte Bedeutung haben.The compounds Ilb6 (≡≡ I with X = 0; R 3 in the 4-position, R 4 in the 5-position and “P (= X) R 1 R 2 ” in the 2-position are also extremely preferred; Q = Q 2 , - R 21 = CH 3 and R 2 = CH 3 ), in particular the compounds Ilb6.n, where the variables R 1 to R 4 and R 20 (in this case corresponds to R 6 ) have the meaning given in Table 1.
Ebenso außerordentlich bevorzugt sind die Verbindungen Ilb7 (Ξ≡ I mit X = 0; R3 in 4 -Position, R4 in 5-Position und „P(=X)R1R7" in 2-Position gebunden; Q = Q2; R21 = CH2CH3 und R22 = CH3), insbesondere die Verbindungen Ilb7.n, wobei die Variablen R1 bis R4 und R20 (entspricht in diesem Fall R6) die in Tabelle 1 genannte Be- deutung haben.The compounds Ilb7 (Ξ≡ I with X = 0; R 3 in the 4-position, R 4 in the 5-position and "P (= X) R 1 R 7 " in the 2-position are also particularly preferably bound; Q = Q 2 ; R 21 = CH 2 CH 3 and R 22 = CH 3 ), in particular the compounds IIb7.n, where the variables R 1 to R 4 and R 20 (in this case corresponds to R 6 ) have the designation given in Table 1 to have an interpretation.
Ebenso außerordentlich bevorzugt sind die Verbindungen Ilb8 (Ξ≡ I mit X = O; R3 in 4 -Position, R4 in 5 -Position und „P(=X)R1R2" in 2-Position gebunden; Q = Q2; R21 = CH(CH3) und R22 = CH3) , insbesondere die Verbindungen Ilbδ.n, wobei die Variablen R1 bis R4 und 20 (entspricht in diesem Fall R6) die in Tabelle 1 genannte Bedeutung haben. The compounds Ilb8 (Ξ≡ I with X = O; R 3 in the 4-position, R 4 in the 5-position and “P (= X) R 1 R 2 ” in the 2-position are also particularly preferred; Q = Q 2 ; R 21 = CH (CH 3 ) and R 22 = CH 3 ), in particular the compounds Ilbδ.n, where the variables R 1 to R 4 and 20 (in this case corresponds to R 6 ) have the meaning given in Table 1 .
Ebenso außerordentlich bevorzugt sind die Verbindungen Ilb9 (Ξ≡ I mit X = 0; R3 in 4 -Position, R4 in 5-Position und „P(=X)R1R2" in 2-Position gebunden; Q = Q2; R21 = C(CH3)3 und R22 = CH3) , insbe- sondere die Verbindungen Ilb9.n, wobei die Variablen R1 bis R4 und R20 (entspricht in diesem Fall R6) die in Tabelle 1 genannte Bedeutung haben.The compounds Ilb9 (Ξ≡ I with X = 0; R 3 in the 4-position, R 4 in the 5-position and “P (= X) R 1 R 2 ” in the 2-position are also extremely preferred; Q = Q 2 ; R 21 = C (CH 3 ) 3 and R 22 = CH 3 ), in particular the compounds Ilb9.n, where the variables R 1 to R 4 and R 20 (in this case corresponds to R 6 ) are those in the table 1 have the meaning given.
Ebenso außerordentlich bevorzugt sind die Verbindungen IlblO (Ξ≡ I mit X = 0; R3 in 4 -Position, R4 in 5-Position und „P(=X)R1R2" in 2-Position gebunden; Q = Q2; R21 = CH2CF3 und R22 = CH3), insbesondere die Verbindungen IlblO.n, wobei die Variablen R1 bis R4 und R20 (entspricht in diesem Fall R6) die in Tabelle 1 genannte Bedeutung haben. The compounds IlblO (Ξ≡ I with X = 0; R 3 in the 4-position, R 4 in the 5-position and “P (= X) R 1 R 2 ” in the 2-position are also extremely preferred; Q = Q 2 ; R 21 = CH 2 CF 3 and R 22 = CH 3 ), in particular the compounds IlblO.n, where the variables R 1 to R 4 and R 20 (in this case corresponds to R 6 ) have the meaning given in Table 1 .
Ebenso außerordentlich bevorzugt sind die Verbindungen Ilbll (Ξ≡ I mit X = 0; R3 in 4 -Position, R4 in 5-Position und „P(=X)R1R2" in 2-Position gebunden; Q = Q2; R21 = CH3 und R22 = CF3) , insbesondere die Verbindungen Ilbll.n, wobei die Variablen R1 bis R4 und R20 (entspricht in diesem Fall R6) die in Tabelle 1 genannte Bedeutung haben.The compounds Ilbll (Ξ≡ I with X = 0; R 3 in the 4-position, R 4 in the 5-position and “P (= X) R 1 R 2 ” in the 2-position are also particularly preferably bound; Q = Q 2 ; R 21 = CH 3 and R 22 = CF 3 ), in particular the compounds Ilbll.n, where the variables R 1 to R 4 and R 20 (in this case corresponds to R 6 ) have the meaning given in Table 1.
IlbllIlbll
Ebenso außerordentlich bevorzugt sind die Verbindungen Ilbl2 (Ξ≡ I mit X = 0; R3 in 4 -Position, R4 in 5-Position und „P(=X)RiR2" in 2-Position gebunden; Q = Q2; R2i = CH2CH3 und R22 = CF3) , insbesondere die Verbindungen Ilbl2.n, wobei die Variablen R1 bis R4 und R20 (entspricht in diesem Fall R6) die in Tabelle 1 genannte Bedeutung haben.The compounds Ilbl2 (Ξ≡ I with X = 0; R 3 in the 4-position, R 4 in the 5-position and “P (= X) RiR 2 ” in the 2-position are also particularly preferably bound; Q = Q 2 ; R 2i = CH 2 CH 3 and R 22 = CF 3 ), in particular the compounds Ilbl2.n, where the variables R 1 to R 4 and R 20 (in this case corresponds to R 6 ) have the meaning given in Table 1.
Ebenso außerordentlich bevorzugt sind die Verbindungen Ilbl3 (≡Ξ I mit X = O; R3 in 4 -Position, R4 in 5 -Position und „P(=X)RR2" in 2-Position gebunden; Q = Q2; R2i = CH(CH3)2 und R22 = CF3) , insbe- sondere die Verbindungen Ilbl3.n, wobei die Variablen R1 bis R4 und R20 (entspricht in diesem Fall R6) die in Tabelle 1 genannte Bedeutung haben.The compounds Ilbl3 (≡Ξ I with X = O; R 3 in the 4-position, R 4 in the 5-position and “P (= X) RR 2 ” in the 2-position are also extremely preferably bound; Q = Q 2 ; R 2i = CH (CH 3 ) 2 and R 22 = CF 3 ), in particular the compounds Ilbl3.n, where the variables R 1 to R 4 and R 20 (in this case corresponds to R 6 ) have the meaning given in Table 1.
Ebenso außerordentlich bevorzugt sind die Verbindungen Ilbl4 (≡= I mit X = 0; R3 in 4 -Position, R4 in 5 -Position und „P(=X)RiR2" in 2-Position gebunden; Q = Q2,- R2i = C(CH3)3 und R22 = CF3) , insbesondere die Verbindungen Ilbl4.n, wobei die Variablen Rl bis R4 und R20 (entspricht in diesem Fall R6) die in Tabelle 1 genannte Bedeutung haben.The compounds Ilbl4 (≡ = I with X = 0; R 3 in the 4-position, R 4 in the 5-position and “P (= X) R i R 2 ” in the 2-position are also particularly preferred; Q = Q 2 , - R 2i = C (CH 3 ) 3 and R 22 = CF 3 ), in particular the compounds Ilbl4.n, where the variables R 1 to R 4 and R 20 (in this case corresponds to R 6 ) are those given in Table 1 Have meaning.
Ebenso außerordentlich bevorzugt sind die Verbindungen Ilbl5 (≡Ξ I mit X = O; R3 in 4 -Position, R4 in 5 -Position und „P(=X)RiR2" in 2-Position gebunden; Q = Q2,- R2l = CH2CF3 und R22 = CF3), insbesondere die Verbindungen Ilbl5.n, wobei die Variablen R1 bis R4 und R20 (entspricht in diesem Fall R6) die in Tabelle 1 genannte Bedeutung haben.The compounds Ilbl5 (≡Ξ I with X = O; R 3 in the 4 position, R 4 in the 5 position and “P (= X) RiR 2 ” in the 2 position are also particularly preferably bound; Q = Q 2 , - R 2 l = CH 2 CF 3 and R 22 = CF 3 ), in particular the compounds Ilbl5.n, where the variables R 1 to R 4 and R 20 (in this case corresponds to R 6 ) have the meaning given in Table 1 .
Ebenso außerordentlich bevorzugt sind die Verbindungen I2bl (≡Ξ I mit X = O; R3 in 2 - Position, R4 in 5 - Position und „ P (=X) RiR2 " in 4 - Position gebunden; Q = Q2 ; R21 = CH3 und R22 = H) , insbesondere die Verbindungen I2bl.n, wobei die Variablen R1 bis R4 und R20 (entspricht in diesem Fall R6) die in Tabelle 1 genannte Bedeutung haben.The compounds I2bl (≡Ξ I with X = O; R 3 in the 2-position, R 4 in the 5-position and "P (= X) RiR 2 " in the 4-position are also particularly preferably bound; Q = Q 2 ; R 21 = CH 3 and R 22 = H), in particular the compounds I2bl.n, where the variables R 1 to R 4 and R 20 (in this case corresponds to R 6 ) have the meaning given in Table 1.
Ebenso außerordentlich bevorzugt sind die Verbindungen I2b2 (-= I mit X = 0; R3 in 2 -Position, R4 in 5 -Position und „P(=X)RiR2" in 4-Position gebunden; Q = Q2; R21 = CH2CH3 und R22 = H) , insbesondere die Verbindungen I2b2.n, wobei die Variablen R1 bis R4 und R20 (entspricht in diesem Fall R6) die in Tabelle 1 genannte Bedeutung haben.The compounds I2b2 (- = I with X = 0; R 3 in the 2-position, R 4 in the 5-position and “P (= X) R i R 2 ” in the 4-position are also extremely preferred; Q = Q 2 ; R 21 = CH 2 CH 3 and R 22 = H), in particular the compounds I2b2.n, where the variables R 1 to R 4 and R 20 (in this case corresponds to R 6 ) have the meaning given in Table 1.
Ebenso außerordentlich bevorzugt sind die Verbindungen I2b3 (Ξ≡ I mit X = O; R3 in 2-Position, R4 in 5-Position und „P(=X)RiR2" in 4-Position gebunden; Q = Q2; R2i = CH(CH3) und R22 = H) , insbesondere die Verbindungen I2b3.n, wobei die Variablen Rl bis R4 und R20 (entspricht in diesem Fall R6) die in Tabelle 1 genannte Be- deutung haben.The compounds I2b3 (Ξ≡ I with X = O; R 3 in the 2-position, R 4 in the 5-position and "P (= X) RiR 2 " in the 4-position are also extremely preferably bound; Q = Q 2 ; R 2i = CH (CH 3 ) and R 22 = H), in particular the compounds I2b3.n, where the variables Rl to R 4 and R 20 (in this case corresponds to R 6 ) have the meaning given in Table 1.
Ebenso außerordentlich bevorzugt sind die Verbindungen I2b4 (= I mit X = 0; R3 in 2 -Position, R4 in 5 -Position und „P(=X)RiR2" in 4-Position gebunden; Q = Q2; R2i = C(CH3)3 und R22 = H) , insbesondere die Verbindungen I2b4.n, wobei die Variablen R1 bis R4 und R2O (entspricht in diesem Fall R6) die in Tabelle 1 genannte Bedeutung haben. The compounds I2b4 (= I with X = 0; R 3 in the 2-position, R 4 in the 5-position and “P (= X) R i R 2 ” in the 4-position are also extremely preferred; Q = Q 2 R 2i = C (CH 3 ) 3 and R 22 = H), in particular the compounds I2b4.n, where the variables R 1 to R 4 and R2 O (in this case corresponds to R 6 ) have the meaning given in Table 1 .
Ebenso außerordentlich bevorzugt sind die Verbindungen I2b5 (Ξ≡ I mit X = 0; R3 in 2 -Position, R4 in 5-Position und „P(=X)RR2" in 4-Position gebunden; Q = Q2; R21 - CH2CF3 und R22 = H) , insbeson- dere die Verbindungen I2b5.n, wobei die Variablen Rl bis R4 und R20 (entspricht in diesem Fall R6) die in Tabelle 1 genannte Bedeutung haben.The compounds I2b5 (Ξ≡ I with X = 0; R 3 in the 2-position, R 4 in the 5-position and "P (= X) RR 2 " in the 4-position are also extremely preferred; Q = Q 2 ; R 21 - CH 2 CF 3 and R 22 = H), in particular the compounds I2b5.n, where the variables R 1 to R 4 and R 20 (in this case corresponds to R 6 ) have the meaning given in Table 1.
Ebenso außerordentlich bevorzugt sind die Verbindungen I2b6 (= I mit X = O; R3 in 2-Position, R4 in 5-Position und „P(=X)RlR2" in 4-Position gebunden; Q = Q2; R21 = CH3 und R22 = CH3) , insbesondere die Verbindungen I2b6.n, wobei die Variablen R1 bis R4 und R20 (entspricht in diesem Fall R6) die in Tabelle 1 genannte Bedeutung haben. The compounds I2b6 (= I with X = O; R 3 in the 2-position, R 4 in the 5-position and "P (= X) RIR 2 " in the 4-position are also particularly preferably bound; Q = Q 2 ; R 21 = CH 3 and R 22 = CH 3 ), in particular the compounds I2b6.n, where the variables R 1 to R 4 and R 20 (in this case corresponds to R 6 ) have the meaning given in Table 1.
Ebenso außerordentlich bevorzugt sind die Verbindungen I2b7 (Ξ≡ I mit X = 0; R3 in 2 -Position, R4 in 5-Position und „P(=X)RiR7" in 24Position gebunden; Q = Q2; R21 = CH2CH3 und R22 = CH3), insbesondere die Verbindungen I2b7.n, wobei die Variablen Rl bis R4 und R20 (entspricht in diesem Fall R6) die in Tabelle 1 genannte Be- deutung haben.The compounds I2b7 (Ξ≡ I with X = 0; R 3 in the 2-position, R 4 in the 5-position and "P (= X) R i R 7 " in the 24-position are also extremely preferred; Q = Q 2 ; R 21 = CH 2 CH 3 and R 22 = CH 3 ), in particular the compounds I2b7.n, where the variables R 1 to R 4 and R 20 (in this case corresponds to R 6 ) have the meaning given in Table 1 .
Ebenso außerordentlich bevorzugt sind die Verbindungen I2b8 (Ξ≡ I mit X = 0; R3 in 2 -Position, R4 in 5-Position und „P(=X)RR2" in 4-Position gebunden; Q = Q2; R21 = CH(CH3)2 und R22 = CH3) , insbesondere die Verbindungen I2b8.n, wobei die Variablen Rl bis R4 und R20 (entspricht in diesem Fall R6) die in Tabelle 1 genannte Bedeutung haben.The compounds I2b8 (Ξ≡ I with X = 0; R 3 in the 2-position, R 4 in the 5-position and "P (= X) RR 2 " in the 4-position are also extremely preferred; Q = Q 2 ; R 21 = CH (CH 3 ) 2 and R 22 = CH 3 ), in particular the compounds I2b8.n, where the variables Rl to R 4 and R 20 (in this case corresponds to R 6 ) have the meaning given in Table 1.
Ebenso außerordentlich bevorzugt sind die Verbindungen Ilb9 (≡Ξ I mit X = 0; R3 in 2 -Position, R4 in 5 -Position und „P(=X)RiR2" in 4-Position gebunden; Q = Q2; R21 = C(CH3)3 und R22 = CH3) , insbe- sondere die Verbindungen I2b9.n, wobei die Variablen Rl bis R4 und R20 (entspricht in diesem Fall R6) die in Tabelle 1 genannte Bedeutung haben.The compounds Ilb9 (≡Ξ I with X = 0; R 3 in the 2-position, R 4 in the 5-position and “P (= X) RiR 2 ” in the 4-position are also particularly preferably bound; Q = Q 2 ; R 21 = C (CH 3 ) 3 and R 22 = CH 3 ), in particular the compounds I2b9.n, where the variables Rl to R 4 and R 20 (in this case corresponds to R 6 ) have the meaning given in Table 1.
Ebenso außerordentlich bevorzugt sind die Verbindungen I2bl0 (Ξ≡ I mit X = 0; R3 in 2 -Position, R4 in 5 -Position und „P(=X)RiR2" in 4-Position gebunden; Q = Q2 ; R21 = CH2CF3 und R22 = CH3), insbesondere die Verbindungen I2bl0.n, wobei die Variablen Ri bis R4 und R20 (entspricht in diesem Fall R6) die in Tabelle 1 genannte Bedeutung haben.The compounds I2bl0 (Ξ≡ I with X = 0; R 3 in the 2-position, R 4 in the 5-position and “P (= X) R i R 2 ” in the 4-position are also extremely preferred; Q = Q 2 ; R 21 = CH 2 CF 3 and R 22 = CH 3 ), in particular the compounds I2bl0.n, where the variables R i to R 4 and R 20 (in this case corresponds to R 6 ) have the meaning given in Table 1 .
Ebenso außerordentlich bevorzugt sind die Verbindungen I2bll (Ξ≡ I mit X = O; R3 in 2 -Position, R4 in 5 -Position und „P(=X)RiR2" in 4 -Position gebunden; Q = Q2; R2i = CH3 und R22 = CF3) , insbesondere die Verbindungen I2bll.n, wobei die Variablen R1 bis R4 und R20 (entspricht in diesem Fall R6) die in Tabelle 1 genannte Bedeutung haben.Likewise, the compounds I2bll (Ξ≡ I with X = O; R 3 in the 2 position, R 4 in the 5 position and “P (= X) R i R 2 ” in the 4 position are particularly preferred; Q = Q 2 ; R 2 i = CH 3 and R 22 = CF 3 ), in particular the compounds I2bll.n, where the variables R 1 to R 4 and R 20 (in this case corresponds to R 6 ) have the meaning given in Table 1.
Ebenso außerordentlich bevorzugt sind die Verbindungen I2bl2 (≡Ξ I mit X = O; R3 in 2 -Position, R4 in 5-Position und „P(=X)R1R2" in 4-Position gebunden; Q = Q2; R21 = CH2CH3 und R22 = CF3) , insbeson- dere die Verbindungen I2bl2.n, wobei die Variablen R1 bis R4 und R20 (entspricht in diesem Fall R6) die in Tabelle 1 genannte Bedeutung haben.The compounds I2bl2 (≡Ξ I with X = O; R 3 in the 2-position, R 4 in the 5-position and “P (= X) R 1 R 2 ” in the 4-position are also extremely preferred; Q = Q 2 ; R 21 = CH 2 CH 3 and R 22 = CF 3 ), in particular the compounds I2bl2.n, where the variables R 1 to R 4 and R 20 (in this case corresponds to R 6 ) have the meaning given in Table 1.
Ebenso außerordentlich bevorzugt sind die Verbindungen I2bl3 (Ξ≡ mit X = 0; R3 in 2-Position, R4 in 5-Position und „P(=X)RiR2" in 4-Position gebunden; Q = Q2; R2i = CH(CH3)2 und R22 = CF3) , insbesondere die Verbindungen I2bl3.n, wobei die Variablen Rx bis R4 und R20 (entspricht in diesem Fall R6) die in Tabelle 1 genannte Bedeutung haben.The compounds I2bl3 (Ξ≡ with X = 0; R 3 in the 2-position, R 4 in the 5-position and "P (= X) R i R 2 " in the 4-position are also particularly preferably bound; Q = Q 2 ; R 2i = CH (CH 3 ) 2 and R 22 = CF 3 ), in particular the compounds I2bl3.n, where the variables R x to R 4 and R 20 (in this case corresponds to R 6 ) have the meaning given in Table 1 to have.
Ebenso außerordentlich bevorzugt sind die Verbindungen Ilbl4 (Ξ≡ mit X = O; R3 in 2 -Position, R4 in 5-Position und „P(=X)RlR2" in 4-Position gebunden; Q = Q2; R2i = C(CH3)3 und R22 = CF3), insbesondere die Verbindungen I2bl4.n, wobei die Variablen R1 bis R4 und R20 (entspricht in diesem Fall R6) die in Tabelle 1 genannte Bedeutung haben.The compounds Ilbl4 (Ξ≡ with X = O; R 3 in the 2-position, R 4 in the 5-position and “P (= X) R 1 R 2 ” in the 4-position are also particularly preferably bound; Q = Q 2 ; R 2i = C (CH 3 ) 3 and R 22 = CF 3 ), in particular the compounds I2bl4.n, where the variables R 1 to R 4 and R 20 (in this case corresponds to R 6 ) have the meaning given in Table 1 to have.
Ebenso außerordentlich bevorzugt sind die Verbindungen I2bl5 (Ξ≡ I mit X = 0; R3 in 2 -Position, R4 in 5-Position und „P(=X)RiR2" in 4-Position gebunden; Q = Q2; R21 = CH2CF3 und R22 = CF3) , insbesondere die Verbindungen I2bl5.n, wobei die Variablen R1 bis R4 und R20 (entspricht in diesem Fall R6) die in Tabelle 1 genannte Bedeutung haben. The compounds I2bl5 (Ξ≡ I with X = 0; R 3 in the 2-position, R 4 in the 5-position and “P (= X) R i R 2 ” in the 4-position are also particularly preferred; Q = Q 2 ; R 21 = CH 2 CF 3 and R 22 = CF 3 ), in particular the compounds I2bl5.n, where the variables R 1 to R 4 and R 20 (in this case corresponds to R 6 ) have the meaning given in Table 1 .
Ebenso außerordentlich bevorzugt sind die Verbindungen Ilcl (Ξ≡ I mit X = 0; R3 in 4 -Position und „P(=X)R1R2" in 2-Position gebunden; Q = Q3; 1 = 0, R23 = Cyclopropyl und R24 = H) , insbesondere die Verbindungen Icl.n, wobei die Variablen Rl bis R3 die in Tabelle 2 genannte Bedeutung haben.The compounds Ilcl (Ξ≡ I with X = 0; R 3 in the 4-position and "P (= X) R 1 R 2 " in the 2-position are also extremely preferred; Q = Q 3 ; 1 = 0, R 23 = cyclopropyl and R 24 = H), in particular the compounds Icl.n, where the variables Rl to R 3 have the meaning given in Table 2.
Tabelle 2 Table 2
Ebenso außerordentlich bevorzugt sind die Verbindungen Ilc2 (Ξ≡ I mit X = 0; R3 in 4 -Position, R4 in 5-Position und „P(=X)RiR2" in 2 -Position gebunden; Q = Q3; R4 = CH3, R23 = Cyclopropyl und R24 = H) , insbesondere die Verbindungen Ilc2.n, wobei die Variablen Ri bis R3 die in Tabelle 2 genannte Bedeutung haben. The compounds Ilc2 (Ξ≡ I with X = 0; R 3 in the 4-position, R 4 in the 5-position and “P (= X) R i R 2 ” in the 2-position are also extremely preferred; Q = Q 3 ; R 4 = CH 3 , R 23 = cyclopropyl and R 24 = H), in particular the compounds Ilc2.n, where the variables R 1 to R 3 have the meaning given in Table 2.
Ebenso außerordentlich bevorzugt sind die Verbindungen Ilc3 (Ξ≡ I mit X = 0; R3 in 4 -Position, R4 in 5-Position und „P(=X)RiR2" in 2 -Position gebunden; Q = Q3; R4 = CI, R23 = Cyclopropyl und R24 = H) , insbesondere die Verbindungen Ilc3.n, wobei die Variablen R1 bis R3 die in Tabelle 2 genannte Bedeutung haben.The compounds Ilc3 (Ξ≡ I with X = 0; R 3 in the 4-position, R 4 in the 5-position and "P (= X) RiR 2 " in the 2-position are also extremely preferably bound; Q = Q 3 ; R 4 = CI, R 23 = cyclopropyl and R 24 = H), in particular the compounds Ilc3.n, where the variables R 1 to R 3 have the meaning given in Table 2.
Ebenso außerordentlich bevorzugt sind die Verbindungen Ilc4 (≡Ξ I mit X = 0; R3 in 4 -Position, R4 in 5-Position und „P(=X)RiR2" in 2 -Position gebunden; Q = Q3; R4 = Br, R23 = Cyclopropyl und R24 = H) , insbesondere die Verbindungen Ilc4, wobei die Variablen R1 bis R3 die in Tabelle 2 genannte Bedeutung haben.The compounds Ilc4 (≡Ξ I with X = 0; R 3 in the 4-position, R 4 in the 5-position and “P (= X) RiR 2 ” in the 2-position are also particularly preferably bound; Q = Q 3 ; R 4 = Br, R 23 = cyclopropyl and R 24 = H), in particular the compounds Ilc4, where the variables R 1 to R 3 have the meaning given in Table 2.
Ebenso außerordentlich bevorzugt sind die Verbindungen I2cl (≡Ξ I mit X = O; R3 in 2-Position und „P(=X)RiR2" in 4-Position gebunden; Q = Q3; 1 = O; R23 = Cyclopropyl und R24 = H) , insbesondere die Verbindungen I2cl.n, wobei die Variablen R1 bis R3 die in Tabelle 2 genannte Bedeutung haben. Likewise, the compounds I2cl (≡Ξ I with X = O; R 3 in the 2-position and "P (= X) R i R 2 " in the 4-position are bound with extreme preference; Q = Q 3 ; 1 = O; R 23 = cyclopropyl and R 24 = H), in particular the compounds I2cl.n, where the variables R 1 to R 3 have the meaning given in Table 2.
Ebenso außerordentlich bevorzugt sind die Verbindungen I2c2 (Ξ≡ I mit X = 0; R3 in 2-Position, R4 in 5-Position und „P(=X)RiR2" in 4 -Position gebunden; Q = Q3; R4 = CH3, R23 = Cyclopropyl und R24 = H) , insbesondere die Verbindungen I2c2.n, wobei die Varia- blen Ri bis R3 die in Tabelle 2 genannte Bedeutung haben.The compounds I2c2 (Ξ≡ I with X = 0; R 3 in the 2-position, R 4 in the 5-position and "P (= X) R i R 2 " in the 4-position are also extremely preferred; Q = Q 3 ; R 4 = CH 3 , R 23 = cyclopropyl and R 24 = H), in particular the compounds I2c2.n, where the variables R i to R 3 have the meaning given in Table 2.
Ebenso außerordentlich bevorzugt sind die Verbindungen I2c3 (Ξ≡ I mit X = O; R3 in 2-Position, R4 in 5-Position und „P(=X)RiR2" in 2 -Position gebunden; Q = Q3; R4 = CI, R23 = Cyclopropyl und R24 = H) , insbesondere die Verbindungen I2c3.n, wobei die Varia - blen R1 bis R3 die in Tabelle 2 genannte Bedeutung haben.The compounds I2c3 (Ξ≡ I with X = O; R 3 in the 2-position, R 4 in the 5-position and "P (= X) RiR 2 " in the 2-position are also extremely preferably bound; Q = Q 3 ; R 4 = CI, R 23 = cyclopropyl and R 24 = H), in particular the compounds I2c3.n, where the variables R 1 to R 3 have the meaning given in Table 2.
Ebenso außerordentlich bevorzugt sind die Verbindungen I2c4 (Ξ≡ I mit X = 0; R3 in 2-Position, R4 in 5-Position und „P(=X)RiR2" in 4-Position gebunden; Q = Q3; R4 = Br, R23 = Cyclopropyl und R24 = H) , insbesondere die Verbindungen I2c4, wobei die Variablen Ri bis R3 die in Tabelle 2 genannte Bedeutung haben. The compounds I2c4 (Ξ≡ I with X = 0; R 3 in the 2-position, R 4 in the 5-position and “P (= X) R i R 2 ” in the 4-position are also particularly preferably bound; Q = Q 3 ; R 4 = Br, R 23 = cyclopropyl and R 24 = H), in particular the compounds I2c4, where the variables Ri to R 3 have the meaning given in Table 2.
Ebenso außerordentlich bevorzugt sind die Verbindungen Ildl (Ξ≡ I mit X = 0; R3 in 4 -Position und „P(=X)RR2" in 2 -Position gebunden; Q = Q4; 1 = 0; R25 = Cyclopropyl) , insbesondere die Verbindungen Ildl.n, wobei die Variablen R1 bis R3 die in Tabelle 2 ge- nannte Bedeutung haben.The compounds Ildl (Ξ≡ I with X = 0; R 3 in the 4 position and "P (= X) RR 2 " in the 2 position are also particularly preferably bound; Q = Q 4 ; 1 = 0; R 25 = Cyclopropyl), in particular the compounds Ildl.n, where the variables R 1 to R 3 have the meaning given in Table 2.
Ebenso außerordentlich bevorzugt sind die Verbindungen Ild2 (Ξ≡ I mit X = 0; R3 in 4-Position, R4 in 5-Position und „P(=X)RiR2" in 2-Position gebunden; Q = Q4; R4 = CH3, R25 = Cyclopropyl), insbesondere die Verbindungen Ild2.n, wobei die Variablen R1 bis R3 die in Tabelle 2 genannte Bedeutung haben.The compounds Ild2 (Ξ≡ I with X = 0; R 3 in the 4-position, R 4 in the 5-position and "P (= X) RiR 2 " in the 2-position are also extremely preferred; Q = Q 4 ; R 4 = CH 3 , R 25 = cyclopropyl), in particular the compounds Ild2.n, where the variables R 1 to R 3 have the meaning given in Table 2.
Ebenso außerordentlich bevorzugt sind die Verbindungen Ild3 (Ξ≡ I mit X = 0; R3 in 4-Position, R4 in 5-Position und „P(=X)RlR2" in 2-Position gebunden; Q = Q4; R4 = CI, R25 = Cyclopropyl), insbesondere die Verbindungen Ild3.n, wobei die Variablen R1 bis R3 die in Tabelle 2 genannte Bedeutung haben. The compounds Ild3 (Ξ≡ I with X = 0; R 3 in the 4-position, R 4 in the 5-position and "P (= X) R 1 R 2 " in the 2-position are also particularly preferably bound; Q = Q 4 ; R 4 = CI, R 25 = cyclopropyl), in particular the compounds Ild3.n, where the variables R 1 to R 3 have the meaning given in Table 2.
CICI
Ebenso außerordentlich bevorzugt sind die Verbindungen Ild4 (Ξ≡ I mit X = 0; R3 in 4 -Position, R4 in 5 -Position und „P(=X)RiR2" in 2-Position gebunden; Q = Q4; R4 = Br, R25 = Cyclopropyl), insbesondere die Verbindungen Ild4, wobei die Variablen R1 bis R3 die in Tabelle 2 genannte Bedeutung haben.The compounds Ild4 (Ξ≡ I with X = 0; R 3 in the 4-position, R 4 in the 5-position and “P (= X) RiR 2 ” in the 2-position are also extremely preferred; Q = Q 4 ; R 4 = Br, R 25 = cyclopropyl), in particular the compounds Ild4, where the variables R 1 to R 3 have the meaning given in Table 2.
Ebenso außerordentlich bevorzugt sind die Verbindungen I2dl (≡Ϊ I mit X = O; R3 in 2 -Position und „P(=X)RiR2" in 4 -Position gebunden; Q = Q4; 1 = 0; R25 = Cyclopropyl) , insbesondere die Verbindungen I2dl.n, wobei die Variablen Rx bis R3 die in Tabelle 2 ge- nannte Bedeutung haben.The compounds I2dl (≡Ϊ I with X = O; R 3 in the 2 position and "P (= X) RiR 2 " in the 4 position are also particularly preferably bound; Q = Q 4 ; 1 = 0; R 25 = Cyclopropyl), in particular the compounds I2dl.n, where the variables R x to R 3 have the meaning given in Table 2.
Ebenso außerordentlich bevorzugt sind die Verbindungen I2d2 (Ξ≡ I mit X = 0; R3 in 4-Position, R4 in 5-Position und „P(=X)RiR2" in 2-Position gebunden; Q = Q4; R4 = CH3, R25 = Cyclopropyl), insbesondere die Verbindungen I2a2.n, wobei die Variablen Ri bis R3 die in Tabelle 2 genannte Bedeutung haben. The compounds I2d2 (Ξ≡ I with X = 0; R 3 in the 4-position, R 4 in the 5-position and "P (= X) R i R 2 " in the 2-position are also extremely preferred; Q = Q 4 ; R 4 = CH 3 , R 25 = cyclopropyl), in particular the compounds I2a2.n, where the variables R i to R 3 have the meaning given in Table 2.
Ebenso außerordentlich bevorzugt sind die Verbindungen I2d3 (== I mit X = 0; R3 in 2-Position, R4 in 5-Position und „P(=X)RiR2" in 2-Position gebunden; Q = Q4; R4 = CI, R25 = Cyclopropyl), insbesondere die Verbindungen I2d3.n, wobei die Variablen R1 bis R3 die in Tabelle 2 genannte Bedeutung haben.The compounds I2d3 (== I with X = 0; R 3 in the 2-position, R 4 in the 5-position and "P (= X) RiR 2 " in the 2-position are also particularly preferably bound; Q = Q 4 ; R 4 = CI, R 25 = cyclopropyl), in particular the compounds I2d3.n, where the variables R 1 to R 3 have the meaning given in Table 2.
Ebenso außerordentlich bevorzugt sind die Verbindungen I2d4 (= I mit X = 0; R3 in 4 -Position, R4 in 5-Position und „P(=X)RiR2" in 2-Position gebunden; Q = Q4; R4 = Br, R25 = Cyclopropyl), insbesondere die Verbindungen I2d4, wobei die Variablen Ri bis R3 die in Tabelle 2 genannte Bedeutung haben.The compounds I2d4 (= I with X = 0; R 3 in the 4-position, R 4 in the 5-position and “P (= X) RiR 2 ” in the 2-position are also extremely preferred; Q = Q 4 ; R 4 = Br, R 25 = cyclopropyl), in particular the compounds I2d4, where the variables R i to R 3 have the meaning given in Table 2.
Die Phosphor-haltigen Benzoyl-Derivate der Formel I sind auf verschiedene Art und Weise erhältlich, beispielsweise nach folgenden Verfahren: The phosphorus-containing benzoyl derivatives of the formula I can be obtained in various ways, for example by the following processes:
A. Darstellung von Verbindungen der Formel la mit R6 = Halogen durch Umsetzung von Verbindungen der Formel la (Ξ≡ I mit Q = Q ) mit R6 = Hydroxy mit Halogenierungsmitteln:A. Preparation of compounds of the formula Ia with R 6 = halogen by reacting compounds of the formula Ia (Ξ≡ I with Q = Q) with R 6 = hydroxy with halogenating agents:
Halogenierungs- mittel la mit R = Halogen Halogenating agent la with R = halogen
la mit R6 = Hydroxyla with R 6 = hydroxy
Als Halogenierungsmittel eignen sich beispielsweise Phosgen, Diphosgen, Triphosgen, Thionylchlorid, Oxalylchlorid, Phosphoroxychlorid, Phosphorpentachlorid, Mesylchlorid, Chlormethylen-N, N-dimethylammoniumchlorid, Oxalylbromid, Phosphoroxybromid etc.Suitable halogenating agents are, for example, phosgene, diphosgene, triphosgene, thionyl chloride, oxalyl chloride, phosphorus oxychloride, phosphorus pentachloride, mesyl chloride, chloromethylene-N, N-dimethylammonium chloride, oxalyl bromide, phosphorus oxybromide etc.
Die Ausgangsverbindungen werden in der Regel im äquimolaren Verhältnis eingesetzt. Es kann aber auch von Vorteil sein, die eine oder andere Komponente im Überschuß einzusetzen.The starting compounds are generally used in an equimolar ratio. However, it can also be advantageous to use one or the other component in excess.
Als Lösungsmittel kommen z.B. chlorierte Kohlenwasserstoffe, wie Methylenchlorid oder 1, 2 -Dichlorethan, aromatische Kohlenwasserstoffe, z.B. Toluol, Xylol oder Chlorbenzol, polare aprotische Lösungsmittel wie Acetonitril, Dimethylform- amid oder Dimethylsulfoxid oder Gemische hiervon in Betracht. Es ist aber auch möglich, die Reaktion in Substanz durchzuführen.Examples of solvents are chlorinated hydrocarbons such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons e.g. Toluene, xylene or chlorobenzene, polar aprotic solvents such as acetonitrile, dimethylformamide or dimethyl sulfoxide or mixtures thereof. However, it is also possible to carry out the reaction in bulk.
In der Regel liegt die Reaktionstemperatur im Bereich von 0°C bis zur Höhe des Siedepunktes des Reaktionsgemisches.As a rule, the reaction temperature is in the range from 0 ° C. to the boiling point of the reaction mixture.
Die Aufarbeitung kann in an sich bekannter Weise zum Produkt hin erfolgen. Darstellung von Verbindungen der Formel la (Ξ≡ I mit Q=Qi) mit 6 = OR13, OS02Ri4, OPR15R6, OPOR5Ri6 oder OPSRi5R16 durch Umsetzung von Verbindungen der Formel la (≡Ξ I mit Q=Q1) mit R6 = Hydroxy mit Alkylierungs- , Sulfonylierungs- bzw. Phos- phonylierungsmitteln Ilα, Ilß, Ilγ, Ilδ bzw. Ilε.The product can be worked up in a manner known per se. Representation of compounds of the formula la (Ξ≡ I with Q = Q i ) with 6 = OR 13 , OS0 2 Ri 4 , OPR 15 R 6 , OPOR 5 R i6 or OPSR i5 R 16 by reacting compounds of the formula la (≡ Ξ I with Q = Q 1 ) with R 6 = hydroxy with alkylating, sulfonylating or phosphonylating agents Ilα, Ilß, Ilγ, Ilδ or Ilε.
la mit R6 = Hydroxyla with R 6 = hydroxy
la mit R6 = ORi3, OS02Ri4, OPR15R16, OPORl5R16 oder OPSRl5Rl6 la with R 6 = OR i3, OS0 2 R i4, OPR 15 R 16, OPOR l5 R 16 or OPSR l5 R l6
L1 steht für eine nucleophil verdrängbare Abgangsgruppe, wie Halogen, z. B. Chlor oder Brom, Hetaryl, z. B. Imidazolyl, Carboxylat, z. B. Acetat, oder Sulfonat, z. B. Mesylat oder Triflat etc.L 1 stands for a nucleophilically displaceable leaving group, such as halogen, e.g. B. chlorine or bromine, hetaryl, e.g. B. imidazolyl, carboxylate, e.g. B. acetate, or sulfonate, e.g. B. mesylate or triflate etc.
Die Verbindungen der Formel Ilα, Ilß, Ilγ, Ilδ oder Ilε können direkt eingesetzt werden wie z. B. im Fall der Carbonsäure- halogenide oder in situ erzeugt werden, z. B. aktivierte Carbonsäuren (mit Carbonsäure und Dicyclohexylcarbodiimid etc. ) .The compounds of formula Ilα, Ilß, Ilγ, Ilδ or Ilε can be used directly, such as. B. in the case of carboxylic acid halides or generated in situ, for. B. activated carboxylic acids (with carboxylic acid and dicyclohexylcarbodiimide etc.).
Die Ausgangsverbindungen werden in der Regel im äquimolaren Verhältnis eingesetzt. Es kann aber auch von Vorteil sein, die eine oder andere Komponente im Überschuß einzusetzen.The starting compounds are generally used in an equimolar ratio. However, it can also be advantageous to use one or the other component in excess.
Gegebenenfalls kann es auch von Vorteil sein, die Umsetzung in Gegenwart einer Base durchzuführen. Die Reaktanden und die Base werden dabei zweckmäßigerweise in äquimolaren Mengen eingesetzt. Ein Überschuß der Base von z.B. 1,5 bis 3 Moläquivalenten kann unter Umständen vorteilhaft sein.If appropriate, it may also be advantageous to carry out the reaction in the presence of a base. The reactants and the base are expediently used in equimolar amounts. An excess of the base e.g. 1.5 to 3 molar equivalents can be advantageous under certain circumstances.
Als Basen eignen sich tertiäre Alkylamine, wie Triethyla in, aromatische Amine, wie Pyridin, Alkalimetallcarbonate, z.B. Natriumcarbonat oder Kaliumcarbonat, Alkalimetallhydrogencar- bonate, wie Natriumhydrogencarbonat und Kaliumhydrogen- carbonat, Alkalimetallalkoholate wie Natriummethanolat, Natriumethanolat, Kalium-tert . -butanolat oder Alkalimetallhy- dide, z.B. Natriumhydrid. Bevorzugt verwendet werden Tri- ethylamin oder Pyridin.Suitable bases are tertiary alkylamines, such as triethylamine, aromatic amines, such as pyridine, alkali metal carbonates, for example sodium carbonate or potassium carbonate, alkali metal hydrogen carbonates, such as sodium hydrogen carbonate and potassium hydrogen carbonate, alkali metal alcoholates such as sodium methoxide, sodium ethanolate, potassium tert. -butanolate or alkali metal hy- dide, eg sodium hydride. Triethylamine or pyridine are preferably used.
Als Lösungsmittel kommen z.B. chlorierte Kohlenwasserstoffe, wie Methylenchlorid oder 1, 2 -Dichlorethan, aromatischeExamples of solvents are chlorinated hydrocarbons, such as methylene chloride or 1,2-dichloroethane, aromatic
Kohlenwasserstoffe, z.B. Toluol, Xylol oder Chlorbenzol, Ether, wie Diethylether, Methyl- tert. -butylether, Tetrahydro- furan oder Dioxan, polare aprotische Lösungsmittel, wie Acetonitril, Dimethylformamid oder Dimethylsulfoxid oder Ester, wie Essigsäureethylester, oder Gemische hiervon in Betracht.Hydrocarbons, e.g. Toluene, xylene or chlorobenzene, ethers such as diethyl ether, methyl tert. butyl ether, tetrahydrofuran or dioxane, polar aprotic solvents such as acetonitrile, dimethylformamide or dimethyl sulfoxide or esters such as ethyl acetate, or mixtures thereof.
In der Regel liegt die Reaktionstemperatur im Bereich von 0°C bis zur Höhe des Siedepunktes des Reaktionsgemisches.As a rule, the reaction temperature is in the range from 0 ° C. to the boiling point of the reaction mixture.
Die Aufarbeitung kann in an sich bekannter Weise zum Produkt hin erfolgen.The product can be worked up in a manner known per se.
Darstellung von Verbindungen der Formel la (Ξ≡ I mit Q = Q1) mit R6 = ORi3, SRi3, PORi5R16, NRi7Ri8, ONR8Ri9, N-gebundenes Heterocyclyl oder 0- (N-gebundenes Heterocyclyl) durch Umsetzung von Verbindungen der Formel la (Ξ≡ I mit Q = Q1) mit R6 = Halogen, OS02Ri4 mit Verbindungen der Formel Illα, HIß, Illγ, Illδ, Illε, Illη oder lir&, gegebenenfalls in Gegenwart einer Base oder unter vorangehender Salzbildung.Representation of compounds of the formula la (Ξ≡ I with Q = Q 1 ) with R 6 = OR i3 , SR i3 , POR i5 R 16 , NR i7 R i8 , ONR 8 R i9 , N-linked heterocyclyl or 0- (N -bound heterocyclyl) by reacting compounds of the formula la (Ξ≡ I with Q = Q 1 ) with R 6 = halogen, OS0 2 R i4 with compounds of the formula Illα, HIß, Illγ, Illδ, Illε, Illη or lir &, if appropriate in the presence of a base or with previous salt formation.
HORi3 (illα) oder HSRi3 (HIß) oder HPORi5Ri6 (Illγ) oder HNRi7R8 (Illδ) oder la mit R6 = Halogen, OS02R14 + HONRl8Ri9 (Illε) oderHOR i3 (illα) or HSR i3 (HIß) or HPOR i5 R i6 (Illγ) or HNR i7 R 8 (Illδ) or la with R 6 = halogen, OS0 2 R 14 + HONRl 8 Ri 9 (Illε) or
H (N-gebundenes Heterocylyl (Illη) oderH (N-linked heterocylyl (Illη) or
H (ON-gebundenes Heterocyclyl) (Iirθ)H (ON-bound heterocyclyl) (Iirθ)
la mit R6 = ORi3, SR13, PORi5Ri6, NRi7Ri8, ONRi7R18, N-gebundenes Heterocyclyl oder ON-gebundenes Heterocyclyl Die Ausgangsverbindungen werden in der Regel im äquimolaren Verhältnis eingesetzt. Es kann aber auch von Vorteil sein, die eine oder andere Komponente im Überschuß einzusetzen.la with R 6 = OR i3 , SR 13 , POR i5 R i6 , NR i7 R i8 , ONR i7 R 18 , N-bound heterocyclyl or ON-bound heterocyclyl The starting compounds are generally used in an equimolar ratio. However, it can also be advantageous to use one or the other component in excess.
Gegebenenfalls kann es auch von Vorteil sein, die Umsetzung in Gegenwart einer Base durchzuführen. Die Reaktanden und die Base werden dabei zweckmäßigerweise in äquimolaren Mengen eingesetzt. Ein Überschuß der Base von z.B. 1,5 bis 3 Moläquivalenten, bezogen auf la (Ξ≡ I mit Q = Qi) mit R6 = Halo- gen, OS02RX4, kann unter Umständen vorteilhaft sein.If appropriate, it may also be advantageous to carry out the reaction in the presence of a base. The reactants and the base are expediently used in equimolar amounts. An excess of the base of, for example, 1.5 to 3 molar equivalents, based on la (Ξ≡ I with Q = Q i ) with R 6 = halogen, OS0 2 R X4 , can be advantageous under certain circumstances.
Als Basen eignen sich tertiäre Alkylamine, wie Triethylamin, aromatische Amine, wie Pyridin, Alkalimetallcarbonate, z.B. Natriumcarbonat oder Kaliumcarbonat, Alkalimetallhydrogencar- bonate, wie Natriumhydrogencarbonat und Kaliumhydrogen- carbonat, Alkalimetallalkoholate wie Natriummethanolat, Natriumethanolat, Kalium- tert . -butanolat oder Alkalimetallhy- dide, z.B. Natriumhydrid. Bevorzugt verwendet werden Natriumhydrid oder Kalium- tert . -butanolat .Suitable bases are tertiary alkyl amines such as triethylamine, aromatic amines such as pyridine, alkali metal carbonates, e.g. Sodium carbonate or potassium carbonate, alkali metal hydrogen carbonates, such as sodium hydrogen carbonate and potassium hydrogen carbonate, alkali metal alcoholates such as sodium methoxide, sodium ethanolate, potassium tert. butanolate or alkali metal hydrides, e.g. Sodium hydride. Sodium hydride or potassium tert are preferably used. -butanolate.
Als Lösungsmittel kommen z.B. chlorierte Kohlenwasserstoffe, wie Methylenchlorid oder 1, 2 -Dichlorethan, aromatische Kohlenwasserstoffe, z.B. Toluol, Xylol oder Chlorbenzol, Ether, wie Diethylether, Methyl-tert . -butylether, Tetrahydro- furan oder Dioxan, polare aprotische Lösungsmittel, wieExamples of solvents are chlorinated hydrocarbons such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons e.g. Toluene, xylene or chlorobenzene, ethers such as diethyl ether, methyl tert. -butyl ether, tetrahydrofuran or dioxane, polar aprotic solvents, such as
Acetonitril, Dimethylformamid oder Dimethylsulfoxid oder Gemische hiervon in Betracht.Acetonitrile, dimethylformamide or dimethyl sulfoxide, or mixtures thereof.
In der Regel liegt die Reaktionstemperatur im Bereich von 0°C bis zur Höhe des Siedepunktes des Reaktionsgemisches.As a rule, the reaction temperature is in the range from 0 ° C. to the boiling point of the reaction mixture.
Die Aufarbeitung kann in an sich bekannter Weise zum Produkt hin erfolgen.The product can be worked up in a manner known per se.
D. Darstellung von Verbindungen der Formel la (Ξ≡ I mit Q = Qi) mit R6 = SOR14, S02Ri4 durch Umsetzung von Verbindungen der Formel la (Ξ≡ I mit Q = Qi) mit R6 = SRX4 mit einem Oxida- tionsmittel.D. Representation of compounds of the formula la (Ξ≡ I with Q = Qi) with R 6 = SOR 14 , S0 2 R i4 by reacting compounds of the formula la (Ξ≡ I with Q = Q i ) with R 6 = SR X4 with an oxidizing agent.
la mi t R6 = SR14 Oxidationsmittel _ I a mi t Re = SQ^4 Qder gQ 14la mi t R 6 = SR 14 oxidizing agent _ I a mi t R e = SQ ^ 4 Qder gQ 14
2-1- Als Oxidationsmittel kommen beispielsweise m-Chlorperbenzoe- säure, Peroxyessigsäure, Trifluorperoxyessigsäure, Wasserstof peroxid, ggf. in Gegenwart eines Katalysators wie Wol- framat, in Betracht.2- 1 - Examples of suitable oxidizing agents are m-chloroperbenzoic acid, peroxyacetic acid, trifluoroperoxyacetic acid, hydrogen peroxide, if appropriate in the presence of a catalyst such as tungstate.
Die Ausgangsverbindungen werden in der Regel im äquimolaren Verhältnis eingesetzt. Es kann aber auch von Vorteil sein, die eine oder andere Komponente im Überschuß einzusetzen.The starting compounds are generally used in an equimolar ratio. However, it can also be advantageous to use one or the other component in excess.
Als Lösungsmittel kommen z.B. chlorierte Kohlenwasserstoffe, wie Methylenchlorid oder 1, 2-Dichlorethan, aromatische Kohlenwasserstoffe, z.B. Toluol, Xylol oder Chlorbenzol, Ether, wie Diethylether, Methyl-tert. -butylether, Tetrahydro- furan oder Dioxan, polare aprotische Lösungsmittel, wie Acetonitril oder Dimethylformamid oder Ester, wie Essigsäure- ethylester, oder Gemische hiervon in Betracht.Examples of solvents are chlorinated hydrocarbons such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons e.g. Toluene, xylene or chlorobenzene, ethers such as diethyl ether, methyl tert. butyl ether, tetrahydrofuran or dioxane, polar aprotic solvents such as acetonitrile or dimethylformamide or esters such as ethyl acetate, or mixtures thereof.
In der Regel liegt die Reaktionstemperatur im Bereich von 0°C bis zur Höhe des Siedepunktes des Reaktionsgemisches.As a rule, the reaction temperature is in the range from 0 ° C. to the boiling point of the reaction mixture.
Die Aufarbeitung kann in an sich bekannter Weise zum Produkt hin erfolgen.The product can be worked up in a manner known per se.
Darstellung von Verbindungen der Formel la (Ξ≡ I mit Q = Q1) mit R6 = OH durch Umsetzung einer aktivierten Phosphor-haltigen Benzoesäure der Formel IVα oder einer Phosphor-haltigen Benzoesäure IVß, die vorzugsweise in situ aktiviert wird, mit einem Cyclohexandion der Formel V zu dem Acylierungsprodukt und anschließende Umlagerung. Representation of compounds of formula la (Ξ≡ I with Q = Q 1 ) with R 6 = OH by reacting an activated phosphorus-containing benzoic acid of the formula IVα or a phosphorus-containing benzoic acid IVß, which is preferably activated in situ, with a cyclohexanedione of the formula V to the acylation product and subsequent rearrangement.
,.
la mi t R6=OH let's say R 6 = OH
L2 steht für eine nucleophil verdrängbare Abgangsgruppe, wie Halogen z.B. Brom oder Chlor, Hetaryl, z.B. Imidazolyl oder Pyridyl, Carboxylat, z.B. Acetat oder Trifluoracetat etc.L 2 stands for a nucleophilically displaceable leaving group, such as halogen, for example bromine or chlorine, hetaryl, for example imidazolyl or pyridyl, carboxylate, for example acetate or trifluoroacetate etc.
Die aktivierte Benzoesäure IVα kann direkt eingesetzt werden, wie im Fall der Benzoylhalogenide oder in situ erzeugt werden, z.B. mit Dicyclohexylcarbodiimid, Triphenylphosphin/Azo- dicarbonsäureester, 2-Pyridindisulfid/Triphenylphosphin, Carbonyldiimidazol etc.The activated benzoic acid IVα can be used directly, as in the case of the benzoyl halides, or generated in situ, e.g. with dicyclohexylcarbodiimide, triphenylphosphine / azodicarboxylic acid ester, 2-pyridine disulfide / triphenylphosphine, carbonyldiimidazole etc.
Gegebenenfalls kann es von Vorteil sein, die Acylierungsreak- tion in Gegenwart einer Base auszuführen. Die Reaktanden und die Hilfsbase werden dabei zweckmäßigerweise in äquimolaren Mengen eingesetzt. Ein geringer Überschuß der Hilfsbase z.B. 1,2 bis 1,5 Moläquivalente, bezogen auf IVα bzw. IVß kann unter Umständen vorteilhaft sein. Als Hilfsbasen eignen sich tertiäre Alkylamine, Pyridin oder Alkalimetallcarbonate. Als Lösungsmittel können z.B. chlorierte Kohlenwasserstoffe, wie Methylenchlorid oder 1, 2-Dichlorethan, aromatische Kohlenwasserstoffe, wie Toluol, Xylol oder Chlorbenzol, Ether, wie Diethylether, Methyl- tert .-butylether, Tetrahydrofuran oder Dioxan, polare aprotische Lösungsmittel, wie Acetonitril, Dimethylformamid oder Dimethylsulfoxid oder Ester wie Essigsäureethylester oder Gemische hiervon verwendet werden.It may be advantageous to carry out the acylation reaction in the presence of a base. The reactants and the auxiliary base are expediently used in equimolar amounts. A slight excess of the auxiliary base, for example 1.2 to 1.5 molar equivalents, based on IVα or IVß may be advantageous under certain circumstances. Tertiary alkyl amines, pyridine or alkali metal carbonates are suitable as auxiliary bases. Examples of suitable solvents are chlorinated hydrocarbons, such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons, such as toluene, xylene or chlorobenzene, ethers, such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran or dioxane, polar aprotic solvents, such as acetonitrile, dimethylformamide or dimethyl sulfoxide or esters such as ethyl acetate or mixtures thereof.
Werden Phosphor-haltige Benzoylhalogenide als aktivierte Carbonsäurekomponente eingesetzt, so kann es zweckmäßig sein, bei Zugabe dieses Reaktionspartners die Reaktionsmischung auf 0-10°C abzukühlen. Anschließend rührt man bei 20 - 100°C, vorzugsweise bei 25 - 50°C, bis die Umsetzung vollständig ist. Die Aufarbeitung erfolgt in üblicher Weise, z.B. wird das Reaktionsgemisch auf Wasser gegossen und das Wertprodukt extrahiert. Als Lösungsmittel eignen sich hierfür besonders Methylenchlorid, Diethylether und Essigsäureethylester. Nach Trocknen der organischen Phase und Entfernen des Lösungsmittels kann der rohe Ester ohne weitere Reinigung zur Umla- gerung eingesetzt werden.If phosphorus-containing benzoyl halides are used as the activated carboxylic acid component, it may be expedient to cool the reaction mixture to 0-10 ° C. when this reactant is added. The mixture is then stirred at 20-100 ° C., preferably at 25-50 ° C., until the reaction is complete. The processing takes place in the usual way, e.g. the reaction mixture is poured onto water and the product of value is extracted. Methylene chloride, diethyl ether and ethyl acetate are particularly suitable as solvents for this. After drying the organic phase and removing the solvent, the crude ester can be used for rearrangement without further purification.
Die Umlagerung der Ester VI zu den Verbindungen der Formel la erfolgt zweckmäßigerweise bei Temperaturen von 20 bis 100°C in einem Lösungsmittel und in Gegenwart einer Base sowie gegebenenfalls mit Hilfe einer Cyanoverbindung als Katalysator.The rearrangement of the esters VI to the compounds of the formula Ia is advantageously carried out at from 20 to 100 ° C. in a solvent and in the presence of a base and, if appropriate, using a cyano compound as a catalyst.
Als Lösungsmittel können z.B. Acetonitril, Methylenchlorid, 1, 2-Dichlorethan, Dioxan, Essigsäureethylester, Toluol oder Gemische hiervon verwendet werden. Bevorzugte Lösungsmittel sind Acetonitril und Dioxan.As a solvent e.g. Acetonitrile, methylene chloride, 1, 2-dichloroethane, dioxane, ethyl acetate, toluene or mixtures thereof can be used. Preferred solvents are acetonitrile and dioxane.
Geeignete Basen sind tertiäre Amine wie Triethylamin, aroma- tische Amine wie Pyridin oder Alkalicarbonate, wie Natrium- carbonat oder Kaliumcarbonat, die vorzugsweise in äquimolarer Menge oder bis zu einem vierfachen Überschuß, bezogen auf den Ester, eingesetzt werden. Bevorzugt werden Triethylamin oder Alkalicarbonat verwendet, vorzugsweise in doppelt äquimolaren Verhältnis in Bezug auf den Ester.Suitable bases are tertiary amines such as triethylamine, aromatic amines such as pyridine or alkali carbonates such as sodium carbonate or potassium carbonate, which are preferably used in an equimolar amount or up to a fourfold excess, based on the ester. Triethylamine or alkali carbonate are preferably used, preferably in a double equimolar ratio with respect to the ester.
Als Cyanoverbindungen kommen anorganische Cyanide, wie Natriumcyanid oder Kaliumcyanid und organische Cyanoverbindungen, wie Acetoncyanhydrin oder Trimethylsilylcyanid in Betracht. Sie werden in einer Menge von 1 bis 50 Molprozent, bezogen auf den Ester, eingesetzt. Vorzugsweise werden Acetoncyanhydrin oder Trimethylsilylcyanid, z.B. in einer Menge von 5 bis 15, vorzugsweise 10 Molprozent, bezogen auf den Ester, eingesetzt.Inorganic cyanides such as sodium cyanide or potassium cyanide and organic cyano compounds such as acetone cyanohydrin or trimethylsilyl cyanide are suitable as cyano compounds. They are used in an amount of 1 to 50 mole percent, based on the ester. Acetone cyanohydrin or trimethylsilyl cyanide, for example in a Amount of 5 to 15, preferably 10 mole percent, based on the ester, used.
Die Aufarbeitung kann in an sich bekannter Weise erfolgen. Das Reaktionsgemisch wird z.B. mit verdünnter Mineralsäure, wie 5 %ige Salzsäure oder Schwefelsäure, angesäuert, mit einem organischen Lösungsmittel, z.B. Methylenchlorid oder Essigsäureethylester extrahiert. Der organische Extrakt kann mit 5-10%iger Alkalicarbonatlösung, z.B. Natriumcarbonat- oder Kaliumcarbonatlösung extrahiert werden. Die wäßrige Phase wird angesäuert und der sich bildende Niederschlag abgesaugt und/oder mit Methylenchlorid oder Essigsäureethylester extrahiert, getrocknet und eingeengt.Working up can be carried out in a manner known per se. The reaction mixture is e.g. acidified with dilute mineral acid such as 5% hydrochloric acid or sulfuric acid, with an organic solvent, e.g. Extracted methylene chloride or ethyl acetate. The organic extract can be mixed with 5-10% alkali carbonate solution, e.g. Sodium carbonate or potassium carbonate solution can be extracted. The aqueous phase is acidified and the precipitate formed is suction filtered and / or extracted with methylene chloride or ethyl acetate, dried and concentrated.
Darstellung von Verbindungen der Ib (≡ I mit Q = Q2) mitRepresentation of compounds of Ib (≡ I with Q = Q 2 ) with
R 0 = Halogen durch Umsetzung von Verbindungen der Formel Ib (Ξ≡ I mit Q = Q2) mit R20 = Hydroxy mit Halogenierungsmitteln:R 0 = halogen by reacting compounds of the formula Ib (Ξ≡ I with Q = Q 2 ) with R 20 = hydroxy with halogenating agents:
Ib mit R20 = HydroxyIb with R 20 = hydroxy
Es gelten die unter Punkt A aufgeführten Ausführungen in Analogie.The explanations listed under point A apply analogously.
Darstellung von Verbindungen der Formel Ib (Ξ≡ I mit Q=Q2) mit R 20 = 0R i3 ( 0S02Ri4, OPR15Rie, OPOR15Ri6 oder OPSR5Ri6 durch Umsetzung von Verbindungen der Formel Ib (Ξ≡ I mit Q=Q2) mit R6 = Hydroxy mit Alkylierungs- , Sulfonylierungs- bzw. Phos- phonylierungsmitteln Ilα, Ilß, Ilγ, Ilδ bzw. Ilε. Representation of compounds of the formula Ib (Ξ≡ I with Q = Q 2 ) with R 20 = 0R i3 ( 0S0 2 R i4 , OPR 15 Rie, OPOR 15 R i6 or OPSR 5 Ri 6 by reacting compounds of the formula Ib (Ξ ≡ I with Q = Q 2 ) with R 6 = hydroxy with alkylating, sulfonylating or phosphonylating agents Ilα, Ilß, Ilγ, Ilδ or Ilε.
Ib mit R20 = HydroxyIb with R 20 = hydroxy
Ib mit R20 = ORi3, OS02Rl4, OPRiSRi6, OPORiSR 6 oder OPSRl5Rl6 Ib with R 20 = OR i3 , OS0 2 Rl 4 , OPRiSRi 6 , OPORiSR 6 or OPSRl 5 Rl 6
Es gelten die unter Punkt B aufgeführten Ausführungen in Analogie. . Darstellung von Verbindungen der Formel Ib (Ξ≡ I mit Q = Q2) mit R6 = ORi3, SRi3, PORiSR6, NRi7Ri8, ONRiβRi9, N-gebundenes Heterocyclyl oder 0- (N-gebundenes Heterocyclyl) durch Umsetzung von Verbindungen der Formel la (≡Ξ I mit Q = Q2) mit R20 = Halogen, OS02Ri4 mit Verbindungen der Formel Illα, HIß, Illγ, Illδ, Illε, Illη oder Iir&, gegebenenfalls in Gegenwart einer Base oder unter vorangehender Salzbildung.The explanations listed under point B apply in analogy. , Representation of compounds of the formula Ib (Ξ≡ I with Q = Q 2 ) with R 6 = OR i3 , SR i3 , POR iS R 6 , NR i7 R i8 , ONR iβ R i9 , N-linked heterocyclyl or 0- (N -bound heterocyclyl) by reacting compounds of the formula la (≡Ξ I with Q = Q 2 ) with R 20 = halogen, OS0 2 R i4 with compounds of the formula Illα, HIß, Illγ, Illδ, Illε, Illη or Iir &, if appropriate in the presence of a base or with previous salt formation.
HORi3 niα oder HORi 3 niα or
HP0Ri5Ri6 (illγ) oderHP0Ri 5 Ri 6 (illγ) or
HNRl?Rl8 (Illδ) oderHNRl ? Rl 8 (Illδ) or
Ib mit R6 = Halogen, 0S02Ri4 + HONRiδRi9 (Illε oder H (N-gebundenes Heterocyclyl (Illη) oder H ( ON - g ebun dene s Heterocyclyl) (III*)Ib with R 6 = halogen, 0S0 2 Ri 4 + HONRi δ R i9 (Illε or H (N-linked heterocyclyl (Illη) or H (ON - found heterocyclyl)) (III *)
Ib mit R 0 = 0RI3, SRi3, PORi5R16, NRi?Ri8, ONRiβRi9' N- gebundenes Heterocyclyl oder ON- gebundenes Heterocyclyl Es gelten die unter Punkt C aufgeführten Ausführungen in Analogie.Ib with R 0 = 0RI 3 , SR i3 , POR i5 R 16 , NR i? Ri 8 , ONR and Ri 9 'N-linked heterocyclyl or ON-linked heterocyclyl The explanations listed under point C apply analogously.
I. Darstellung von Verbindungen der Formel Ib (Ξ≡ I mit Q = Q2) mit R20 = SOR14, S02Ri4 durch Umsetzung von Verbindungen der Formel Ib (= I mit Q = Q2) mit R20 = SRi4 mit einem Oxida- tionsmittel .I. Representation of compounds of the formula Ib (Ξ≡ I with Q = Q 2 ) with R 20 = SOR 14 , S0 2 R i4 by reacting compounds of the formula Ib (= I with Q = Q 2 ) with R 20 = SR i4 with an oxidizing agent.
Oxidations ittelOxidation agent
Ib mit R6 = SR8 Ib mit R6 = SOR8 oder S02RIb with R 6 = SR 8 Ib with R 6 = SOR 8 or S0 2 R
Es gelten die unter Punkt D aufgeführten Ausführungen in Analogie.The explanations listed under point D apply analogously.
K. Darstellung von Verbindungen der Formel Ib (Ξ≡ I mit Q = Q2) R2Ö Φ Hydroxy durch Umsetzung eines metallierten Pyrazol-De- rivats der Formel VII mit einem Phosphor-haltigen Benzoesäure-Derivat der Formel Vlγ:K. Preparation of compounds of the formula Ib (Ξ≡ I with Q = Q 2 ) R2 Ö Φ hydroxy by reacting a metalated pyrazole derivative of the formula VII with a phosphorus-containing benzoic acid derivative of the formula VI:
VII mi t R20 Φ Hydroxy ivγ Ib mit R20 * HydroxyVII with R 20 Φ hydroxy ivγ Ib with R 20 * hydroxy
M steht hierbei für ein Metall, insbesondere für ein Alkali - metall wie Lithium oder Natrium, ein Erdalkalimetall wie z.B. Magnesium oder ein Übergangsmetall wie Palladium, Nickel etc. und L3 für eine nucleophil verdrängbare Abgangsgruppe wie Halogen, z.B. Chlor oder Brom, Alkylsulfonat wie Mesylat, Halogenalkylsulfonat wie Triflat oder Cyanid.M stands for a metal, in particular for an alkali metal such as lithium or sodium, an alkaline earth metal such as magnesium or a transition metal such as palladium, nickel etc. and L 3 for a nucleophilically displaceable leaving group such as halogen, such as chlorine or bromine, alkyl sulfonate such as Mesylate, haloalkyl sulfonate such as triflate or cyanide.
Die Umsetzung wird in der Regel bei Temperaturen von -100°C bis Rückflußtemperatur des Reaktionsgemisches durchgeführt. Als Lösungsmittel eignen sich inerte aprotische Lösungsmittel, wie Ether, z.B. Diethylether, Tetrahydrofuran. Die Verbindungen der Formel IVγ werden in der Regel im Überschuß eingesetzt, es kann aber auch von Vorteil sein, diese in äquimolaren Mengen oder im Unterschuß einzusetzen. Die Aufarbeitung erfolgt zum Produkt hin. Die metallierten Pyrazol -Derivate der Formel VII können auf an sich bekannte Art und Weise durch Umsetzung von in 4 -Position halogenierten Pyrazolen mit Metallen wie Lithium, Natrium, Magnesium etc. oder mit metallorganischen Verbindungen wie z.B. Butyllithiu gebildet werden. Es ist aber auch möglich Pyrazole, die in 4 -Position mit Wasserstoff verknüpft sind, direkt zu metallieren, z.B. mit den voranstehend genannten Metallen bzw. metallorganischen Verbindungen. Die Umsetzungen werden in der Regel in einem inerten aprotischen Lösungsmittel durchgeführt, bevorzugt in Ether wie Diethylether, Tetrahydrofuran etc.. Die Reaktionstemperatur liegt im Bereich von -100°C bis zur Höhe des Siedepunktes des Reaktionsgemisches. Die Verbindungen der Formel VII werden in der Regel direkt weiter umgesetzt oder in situ erzeugt.The reaction is usually carried out at temperatures from -100 ° C. to the reflux temperature of the reaction mixture. Inert aprotic solvents such as ethers, for example diethyl ether, tetrahydrofuran, are suitable as solvents. The compounds of the formula IVγ are generally used in excess, but it may also be advantageous to use them in equimolar amounts or in a deficit. The processing takes place towards the product. The metalated pyrazole derivatives of the formula VII can be formed in a manner known per se by reacting pyrazoles halogenated in the 4-position with metals such as lithium, sodium, magnesium etc. or with organometallic compounds such as butyllithium. However, it is also possible to directly metallize pyrazoles which are linked to hydrogen in the 4-position, for example using the metals or organometallic compounds mentioned above. The reactions are generally carried out in an inert aprotic solvent, preferably in ethers such as diethyl ether, tetrahydrofuran etc. The reaction temperature is in the range from -100 ° C. to the boiling point of the reaction mixture. The compounds of the formula VII are generally reacted further directly or produced in situ.
Darstellung von Verbindungen der Formel Ib (Ξ≡ I mit Q=Q2) mit R 20 = Hydroxy durch Umsetzung einer aktivierten Phosphor-haltigen Benzoesäure der Formel IVα oder einer Phosphor-haltigen Benzoesäure IVß, die vorzugsweise in situ aktiviert wird, mit einem Pyrazol der Formel VIII zu dem Acylierungsprodukt und anschließende Umlagerung. Representation of compounds of formula Ib (Ξ≡ I with Q = Q 2 ) with R 20 = hydroxy by reacting an activated phosphorus-containing benzoic acid of formula IVα or a phosphorus-containing benzoic acid IVß, which is preferably activated in situ, with a pyrazole of formula VIII to the acylation product and subsequent rearrangement.
Ib mit R20 = HydroxyIb with R 20 = hydroxy
Es gelten die unter Punkt E aufgeführten Ausführungen in Analogie.The explanations listed under point E apply in analogy.
Es ist aber auch möglich, den Ester IX in situ zu erzeugen, indem man ein Pyrazol der Formel VIII, oder ein Alkalisalz hiervon, mit einem Phosphor-haltigen Benzolderivat der Formel X in Gegenwart von Kohlenmonoxid, eines Katalysators sowie einer Base, umsetzt. However, it is also possible to produce the ester IX in situ by reacting a pyrazole of the formula VIII, or an alkali salt thereof, with a phosphorus-containing benzene derivative of the formula X in the presence of carbon monoxide, a catalyst and a base.
L4 steht für eine Abgangsgruppe wie Halogen, z.B. Chlor, Brom oder lod, oder Sulfonat wie Mesylat oder Triflat; bevorzugt sind Brom oder Triflat.L 4 stands for a leaving group such as halogen, for example chlorine, bromine or iodine, or sulfonate such as mesylate or triflate; bromine or triflate are preferred.
Der Ester IX reagiert ggf. direkt zu dem Phosphor-haltigen Benzoyl-Derivat der Formel Ib ab.The ester IX may react directly to the phosphorus-containing benzoyl derivative of the formula Ib.
Als Katalysatoren eignen sich Palladiumligandkomplexe, in denen das Palladium in der Oxidationsstufe 0 vorliegt, metallisches Palladium, das gegebenenfalls auf einen Träger aufgezo- gen wurde, und vorzugsweise Palladium (II) salze. Die Umsetzung mit Palladium(II) salzen und metallischem Palladium wird vorzugsweise in Gegenwart von Komplexliganden durchgeführt.Suitable catalysts are palladium ligand complexes in which the palladium is in oxidation state 0, metallic palladium, which has optionally been applied to a support, and preferably palladium (II) salts. The reaction with palladium (II) salts and metallic palladium is preferably carried out in the presence of complex ligands.
Als Palladium (0) ligandkomplex kommt beispielsweise Tetra- kis (triphenylphosphan) palladium in Frage.As a palladium (0) ligand complex, for example, tetrakis (triphenylphosphine) palladium can be used.
Metallisches Palladium ist vorzugsweise auf einen inerten Träger wie beispielsweise Aktivkohle, Siliciumdioxid, Aluminiumoxid, Bariumsulfat oder Calciumcarbonat aufgezogen. Die Reaktion wird vorzugsweise in Gegenwart von Komplexliganden wie beispielsweise Triphenylphosphan durchgeführt.Metallic palladium is preferably coated on an inert support such as activated carbon, silicon dioxide, aluminum oxide, barium sulfate or calcium carbonate. The reaction is preferably carried out in the presence of complex ligands such as triphenylphosphine.
Als Palladium(II) salze eigenen sich beispielsweise Palladium- acetat und Palladiumchlorid. Bevorzugt wird in Gegenwart von Komplexliganden wie beispielsweise Triphenylphosphan gearbeitet. Geeignete Komplexliganden für die Palladiumligandkomplexe, bzw. in deren Gegenwart die Umsetzung mit metallischem Palladium oder Palladium (II) salzen vorzugsweise ausgeführt wird, sind tertiäre Phosphane, deren Struktur durch folgende For- mein wiedergegeben wird:Suitable palladium (II) salts are, for example, palladium acetate and palladium chloride. It is preferred to work in the presence of complex ligands such as triphenylphosphine. Suitable complex ligands for the palladium ligand complexes, or in the presence of which the reaction with metallic palladium or palladium (II) salts is preferably carried out, are tertiary phosphines, the structure of which is given by the following formula:
wobei z die Zahlen 1 bis 4 bedeutet und die Reste Ra bis R9 für Cχ-C6-Alkyl, Aryl-Cι~C2-alkyl oder vorzugsweise Aryl stehen. Aryl steht beispielsweise für Naphthyl und gegebenen- falls substituiertes Phenyl wie beispielsweise 2-Tolyl und insbesondere für unsubstituiertes Phenyl.where z is the numbers 1 to 4 and the radicals R a to R9 are Cχ-C 6 alkyl, aryl-Cι ~ C 2 alkyl or preferably aryl. Aryl stands for example for naphthyl and optionally substituted phenyl such as 2-tolyl and in particular for unsubstituted phenyl.
Die Herstellung der komplexen Palladiumsalze kann in an sich bekannter Weise ausgehend von kommerziell erhältlichen Palla- diumsalzen wie Palladiumchlorid oder Palladiumacetat und den entsprechenden Phosphanen wie z.B. Triphenylphosphan oder 1, 2-Bis (diphenylphosphano) ethan erfolgen. Ein Großteil der komplexierten Palladiumsalze ist auch kommerziell erhältlich. Bevorzugte Palladiumsalze sind [ (R) (+) 2, 2 ' -Bis (diphenylphos- phano) -1, l'-binaphthyl] palladium (II) chlorid, Bis (triphenylphosphan) palladium (II) acetat und insbesondere Bis (triphenyl - phosphan) palladium (II) chlorid.The complex palladium salts can be prepared in a manner known per se from commercially available palladium salts such as palladium chloride or palladium acetate and the corresponding phosphanes such as e.g. Triphenylphosphan or 1, 2-bis (diphenylphosphano) ethane take place. Most of the complexed palladium salts are also commercially available. Preferred palladium salts are [(R) (+) 2,2'-bis (diphenylphosphane) -1, l'-binaphthyl] palladium (II) chloride, bis (triphenylphosphine) palladium (II) acetate and in particular bis (triphenyl - phosphine) palladium (II) chloride.
Der Palladiumkatalysator wird in der Regel in einer Konzen- tration von 0,05 bis 5 Mol%, bevorzugt 1-3 Mol%, eingesetzt.The palladium catalyst is generally used in a concentration of 0.05 to 5 mol%, preferably 1-3 mol%.
Als Basen kommen tertiäre Amine wie beispielsweise N-Methyl - piperidin, Ethyldiisopropylamin, 1, 8-Bisdimethylaminonaphtha- lin oder insbesondere Triethylamin in Betracht. Ebenso eige- nen sich Alkalicarbonat, wie Natriumcarbonat oder Kalium- carbonat. Aber auch Gemische von Kaliumcarbonat und Triethylamin sind geeignet.Suitable bases are tertiary amines such as, for example, N-methylpiperidine, ethyldiisopropylamine, 1,8-bisdimethylaminonaphthalene or, in particular, triethylamine. Alkali carbonate, such as sodium carbonate or potassium carbonate, are also suitable. Mixtures of potassium carbonate and triethylamine are also suitable.
In der Regel werden 2 bis 4 Moläquivalente, insbesondere 2 Moläquivalente, des Alkalicarbonats, sowie 1 bis 4 Moläquivalente, insbesondere 2 Moläquivalente des tertiären Amins bezogen auf das Phosphor-haltige Benzolderivat der Formel X eingesetzt.As a rule, 2 to 4 molar equivalents, in particular 2 molar equivalents, of the alkali metal carbonate, and 1 to 4 molar equivalents, in particular 2 molar equivalents, of the tertiary amine, based on the phosphorus-containing benzene derivative of the formula X, are used.
Als Lösungsmittel können Nitrile wie Benzonitril und Acetonitril, Amide wie Dimethylformamid, Dimethylacetamid, Te- tra-Cι-C-alkylharnstoffe oder N-Methylpyrrolidon und Vorzugs- weise Ether wie Tetrahydrofuran, Methyl-tert. -butylether dienen. Insbesondere werden Ether wie 1,4-Dioxan und Dimethoxye- than als Lösungsmittel bevorzugt.Nitriles such as benzonitrile and acetonitrile, amides such as dimethylformamide, dimethylacetamide, tetra-C 1 -C 8 -alkylureas or N-methylpyrrolidone and preferred wise ethers such as tetrahydrofuran, methyl tert. serve butyl ether. In particular, ethers such as 1,4-dioxane and dimethoxyethane are preferred as solvents.
Darstellung von Verbindungen der Formel Ic (≡≡ I mit Q=Q3) mit R24 = H durch Umsetzung einer 1, 3 -DicarbonylVerbindung der Formel XI mit Hydroxylamin.Preparation of compounds of the formula Ic (≡≡ I with Q = Q 3 ) with R 24 = H by reacting a 1,3-dicarbonyl compound of the formula XI with hydroxylamine.
XI IC mit R24 - HXI IC with R 24 - H
L5 steht für eine O-Ci-Cβ-Alkyl oder N (Ci-Cö-Alkyl) 2-Gruppe. Die 1, 3 -Dicarbonylverbindung der Formel XI wird mit Hydroxylamin, das in situ erzeugt wird, z.B. aus einem Salz von Hydroxylamin mit einer Base oder einen Säureakzeptor wie Triethylamin oder Natriumacetat, umgesetzt.L 5 stands for an O-Ci-Cβ-alkyl or N (Ci-C ö -alkyl) 2 group. The 1,3-dicarbonyl compound of the formula XI is reacted with hydroxylamine which is generated in situ, for example from a salt of hydroxylamine with a base or an acid acceptor such as triethylamine or sodium acetate.
Die Ausgangsverbindung der Formel XI erhält man, indem man die an sich bekannten ß-Ketoester der Formel XII mit einer aktivierten Phosphor-haltigen Benzoesäure IVα umsetzt. Anschließend wird das Acylierungsprodukt XIII beispielsweise mit p-Toluolsulfonsäure als Katalysator in einem inerten Lösungsmittel wie Toluol in das 1,3-Diketon XIV überführt. Dieses wird anschließend mit einem Orthoester oder Dimethylfor- mamiddialkylacetal zu der 1, 3 -Dicarbonylverbindung der Formel XI umgesetzt. The starting compound of the formula XI is obtained by reacting the known β-keto esters of the formula XII with an activated phosphorus-containing benzoic acid IVα. The acylation product XIII is then converted, for example using p-toluenesulfonic acid as catalyst, into the 1,3-diketone XIV in an inert solvent such as toluene. This is then reacted with an orthoester or dimethylformamide dialkyl acetal to give the 1,3-dicarbonyl compound of the formula XI.
XII IVαXII IVα
XIII XIVXIII XIV
XIXI
N. Darstellung von Verbindungen der Formel Ic (Ξ≡ I mit Q=Q3) durch Cycloaddition des α,ß-ungesättigten Benzoylderivats XV mit einem Nitriloxid der Formel XVIN. Preparation of compounds of the formula Ic (Ξ≡ I with Q = Q 3 ) by cycloaddition of the α, β-unsaturated benzoyl derivative XV with a nitrile oxide of the formula XVI
XV XVI IC Das α,ß-ungesättigten Benzoylderivats XV wird durch Ethiny- lierung der aktivierten phosphorhaltigen Benzoesäure der Formel IVα erhalten.XV XVI IC The α, β-unsaturated benzoyl derivative XV is obtained by ethinating the activated phosphorus-containing benzoic acid of the formula IVα.
Z steht für ein Metall wie Lithium, einen zinnorganischen Rest wie Sn(C4H9)3 oder einen Zink-Rest wie ZnCl oder ZnBr.Z stands for a metal such as lithium, an organotin residue such as Sn (C 4 H 9 ) 3 or a zinc residue such as ZnCl or ZnBr.
O. Darstellung von Verbindungen der Formel Id (Ξ≡ I mit Q=Q4) durch Umsetzung des Cyanoketons XVII mit einer aktivierten Phosphor-haltigen Benzoesäure der Formel IVα in Gegenwart einer Base wie Triethylamin, Natriumcarbonat, Natriumhydrid oder Magnesiumethanolat in einem inerten organischen Lösungsmittel wie Diethylether, Tetrahydrofuran, N,N-Diethylforma- mid, Dichlormethan oder Acetonitril.O. Preparation of compounds of the formula Id (Ξ≡ I with Q = Q 4 ) by reacting the cyanoketone XVII with an activated phosphorus-containing benzoic acid of the formula IVα in the presence of a base such as triethylamine, sodium carbonate, sodium hydride or magnesium ethanolate in an inert organic solvent such as diethyl ether, tetrahydrofuran, N, N-diethylformamide, dichloromethane or acetonitrile.
XVII IVα IdXVII IVα Id
Die Phosphor -haltigen Benzloylhalogenide der Formel IVα mit L2 = Halogen können auf an sich bekannte Art und Weise durch Umsetzung der Benzoesäuren der Formel IVß mit Halogenierungs- reagentien wie Thionylchlorid, Thionylbromid, Phosgen, Diphosgen, Triphosgen, Oxalylchlorid, Oxalylbromid hergestellt werden.The phosphorus-containing benzloyl halides of the formula IVα with L 2 = halogen can be prepared in a manner known per se by reacting the benzoic acids of the formula IVß with halogenating reagents such as thionyl chloride, thionyl bromide, phosgene, diphosgene, triphosgene, oxalyl chloride and oxalyl bromide.
Die Phosphor -haltigen Benzoesäuren der Formel IVß in bekannter weise durch saure oder basische Hydrolyse aus den entsprechenden Phosphor-haltigen Benzoesäureestern ivδ hergestellt werden (vgl. j. March, "Advanced Organic Chemistry" , 4. Auflage, Wiley, New York, S. 378 ff . )The phosphorus-containing benzoic acids of the formula IVß are prepared in a known manner by acidic or basic hydrolysis from the corresponding phosphorus-containing benzoic acid esters ivδ (cf. j. March, "Advanced Organic Chemistry", 4th edition, Wiley, New York, pp. 378 ff. )
wobei T für CI-CÖ -Alkoxy steht.where T is C I -C Ö alkoxy.
Die Phosphor -haltigen Benzoesäureester IV δ sind auf verschiedene Art und Weise erhältlich:The phosphorus-containing benzoic acid esters IV δ are available in different ways:
Sie können durch elektrophile oder nukleophile aromatische Substitution von Benzoesäureestern der Formel XVIII und gegebenenfalls weiterer Funktinalisierung der so eingeführten Gruppe erhalten werden.They can be obtained by electrophilic or nucleophilic aromatic substitution of benzoic acid esters of the formula XVIII and, if appropriate, further functionalization of the group introduced in this way.
Beispielsweise kann der Ester der Formel XVIII in Analogie zu bekannten Methoden nitriert (R3=N02; vgl. J. March, "Advanced Organic Chemistry", 4. Auflage, S. 522 ff.), bromiert oder chloriert (R3=C1, Br; vgl. J. March, "Advanced Organic Chemistry", 4. Auflage, S. 531 ff.) werden.For example, the ester of formula XVIII can be nitrated analogously to known methods (R 3 = N0 2 ; cf. J. March, "Advanced Organic Chemistry", 4th edition, p. 522 ff.), Brominated or chlorinated (R 3 = C1, Br; see J. March, "Advanced Organic Chemistry", 4th edition, p. 531 ff.).
Bei der oben genannten elektrophilen aromatischen Substitutionsreaktion entstehen ggf. Isomerengemische, die durch Destillation, Kristallisation oder chromatografische Methoden getrennt bzw. gereinigt werden können. Phosphor -haltige Benzoesäureester der Formel IV δ mit R3=NH2 können durch Reduktion der entsprechenden Nitroverbindungen der Formel IV δ mit R3=N0 erhalten werden.The above-mentioned electrophilic aromatic substitution reaction may result in isomer mixtures which can be separated or purified by distillation, crystallization or chromatographic methods. Phosphorus-containing benzoic acid esters of the formula IV δ with R 3 = NH 2 can be obtained by reducing the corresponding nitro compounds of the formula IV δ with R 3 = N0.
IVδ mit R3=N02 IVδ mit R3=NH2 IVδ with R 3 = N0 2 IVδ with R 3 = NH 2
Als Reduktionsmittel kommen u.a. Metalle wie Eisen oder Zink, in Gegenwart von Salzsäure und katalytisch aktivierter Wasserstoff in Betracht, (vgl. J. March, "Advanced Organic Chemistry", 4. Auflage, S. 1216 ff.)The reducing agents include Metals such as iron or zinc, in the presence of hydrochloric acid and catalytically activated hydrogen, (see J. March, "Advanced Organic Chemistry", 4th edition, p. 1216 ff.)
Phosphor -haltige Benzoesäureester der Formel IV δ mit R3 = (CI-CÖ -Alkylsulfonyl) amino, (CI-CÖ -Halogenalkylsulfo- nyl) amino können durch Reaktion der entsprechenden Amino-Ver- bindungen mit geeignet substituierten Sulfonsäurechloriden in Gegenwart einer Base erhalten werden, (vgl. T.W. Green et al., "Protective Groups in Organic Synthesis" , S. 379 f.)Phosphorus-containing benzoic acid esters of the formula IV δ with R 3 = (C I -C Ö alkylsulfonyl) amino, (C I -C Ö haloalkylsulfonyl) amino can be obtained by reacting the corresponding amino compounds with suitably substituted sulfonic acid chlorides in Presence of a base can be obtained, (see TW Green et al., "Protective Groups in Organic Synthesis", p. 379 f.)
Cι - C6 -Halogenalkyl IVδ mi R3=NH2 IVδ mi t R3=NHS02R 'Cι - C 6 haloalkyl IVδ mi R 3 = NH 2 IVδ mi t R 3 = NHS0 2 R '
Letztere können durch Alkylierung in Gegenwart einer Base in die entsprechenden N-Alkyl -Derivate übergeführt werden. The latter can be converted into the corresponding N-alkyl derivatives by alkylation in the presence of a base.
R" S02-R'R "S0 2 -R '
IVδ mi t R3=NHS02R' IVδ mit R3=N"S02R'IVδ with R 3 = NHS0 2 R 'IVδ with R 3 = N "S0 2 R'
Als Base können u.a. Natriumhydrid, Kaliumhydrid, Kalium- tert -butanolat und als Alkylhalogenid Alkylbromide und Alkyl- iodide dienen. (Vgl. J.P. Dünn et al., J. Med. Chem. 1981, 24, S. 1097) .As a base, i.a. Sodium hydride, potassium hydride, potassium tert-butoxide and as alkyl halide, alkyl bromides and alkyl iodides are used. (See J.P. Dünn et al., J. Med. Chem. 1981, 24, p. 1097).
Phosphor-haltige Benzoesäureester der Formel IVδ mit R3 = Halogen, Cyano, Ci-Cö-Alkyl, Cι-C6 -Aikylthio oder Cι-C6 -Halogenalkylthio können durch Sandmeyer-Reaktion oder verwandte Reaktionen aus den entsprechenden Amino -Verbindungen erhalten werden, (vgl. J. March, "Advanced Organic Chemistry", 4. Auf läge, S. 723-724, S. 669-671) Phosphorus-containing benzoic esters of the formula IVδ with R 3 = halogen, cyano, Ci-C ö -alkyl, C 6 -Aikylthio or Cι-C6 haloalkylthio can be obtained by Sandmeyer reaction or related reactions from the corresponding amino compounds (see J. March, "Advanced Organic Chemistry", 4th edition, pp. 723-724, pp. 669-671)
II.
R' = Cι-C6 -Alkyl,R '= -C 6 alkyl,
Ci - C6 - Halogenalkyl Gegebenenfalls kann es von Vorteil sein, die Reaktionen in Gegenwart von Metallkatalysatoren wie z.B. Kupfer (I) oder Palladium (II) durchzuführen (vgl. z.B. Kikukawa et al., J. Org. Chem. 1983, 48, 1333)Ci - C 6 - haloalkyl It may be advantageous to carry out the reactions in the presence of metal catalysts such as copper (I) or palladium (II) (see, for example, Kikukawa et al., J. Org. Chem. 1983, 48, 1333)
Phosphor -haltige Benzoesäureester der Formel IVδ mit R3 = S(O) ι/2-Cι-C6-Alkyl oder S(0)ι/2- Cι-C6 -Halogenalkyl können durch Umsetzung der entsprechenden Schwefel -Verbindungen mit einem Oxidationsmittel wie Brom, Peroxyessigsäure, m-Chlorperbenzoesäure und Wasserstoffperoxid, gegebenenfalls in Gegenwart eines Katalysators wie Wolframat, erhalten werden.Phosphorus-containing benzoic acid esters of the formula IVδ with R 3 = S (O) ι / 2 -Cι-C 6 alkyl or S (0) ι / 2 - Cι-C 6 haloalkyl can be reacted with a corresponding sulfur compounds Oxidizing agents such as bromine, peroxyacetic acid, m-chloroperbenzoic acid and hydrogen peroxide, optionally in the presence of a catalyst such as tungstate, can be obtained.
ι- 6 -Ha ogena y IVδ mi t R3=NH2 IVδ mit R3=S(0)1/2R' ι- 6 -Ha ogena y IVδ with R 3 = NH 2 IVδ with R 3 = S (0) 1/2 R '
Phosphor-haltige Benzoesäureester der Formel IVδ mit R3 = Aminosulfonyl, Cι-C6 -Alkylaminosulfonyl oder Di (Cι-C6-alkyl) aminosulfonyl können durch Umsetzung des entsprechenden Sulfonsäurechlorids mit Ammoniak bzw. geeigneten Aminen erhalten werden. Gegebenenfalls kann es in Betracht kommen in Gegenwart einer Base wie Triethylamin, Natriumcarbonat, Kali- umcarbonat, Natriumhydrogencarbonat, Kaliumhydrogencarbonat oder Pyridin zu arbeiten (vgl. J. March, "Advanced Organic Chemistry", 4. Auflage, S. 499). Das Sulfonsäurechlorid erhält man durch Sulfochlorierung des entsprechenden Diazonium- salzes . Phosphorus-containing benzoic acid esters of the formula IVδ with R 3 = aminosulfonyl, C 1 -C 6 -alkylaminosulfonyl or di (C 1 -C 6 -alkyl) aminosulfonyl can be obtained by reacting the corresponding sulfonic acid chloride with ammonia or suitable amines. If appropriate, it can be considered to work in the presence of a base such as triethylamine, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or pyridine (cf. J. March, "Advanced Organic Chemistry", 4th edition, p. 499). The sulfonic acid chloride is obtained by sulfochlorination of the corresponding diazonium salt.
IVδ mit R3=NH2 IVδ with R 3 = NH 2
IVδ mit R3=S02NR2'"IVδ with R 3 = S0 2 NR 2 '"
Phosphor -haltige Benzoesäureester der Formel IVδ mit R3 = Cι-C6 -Alkoxy oder Cχ-C6 -Halogenalkoxy können durch Alky- lierung der entsprechenden Phenole in Gegenwart einer Base erhalten werden. Als Basen eignen sich neben den üblichen Basen insbesondere Natriumcarbonat, Kaliumcarbonat, Natriumhydrid oder Kalium- tert . -butanolat. Als Alkylierungsagentien kommen bevorzugt entsprechende ggf. halogenierte Alkylbromide bzw. -chloride in Betracht (vgl. z.B. H. Fener et al . , "The Chemistry of the Ether Linkage" , Wiley, New York, 1967, S. 445-498.)Phosphorus-containing benzoic acid esters of the formula IVδ with R 3 = -CC 6 -alkoxy or Cχ-C 6 -haloalkoxy can be obtained by alkylation of the corresponding phenols in the presence of a base. In addition to the usual bases, suitable bases are in particular sodium carbonate, potassium carbonate, sodium hydride or potassium tert. -butanolate. Suitable alkylation agents are preferably halogenated alkyl bromides or chlorides which may be halogenated (see, for example, H. Fener et al., "The Chemistry of the Ether Linkage", Wiley, New York, 1967, pp. 445-498.)
Die Phenole sind mittels "Verkochung" entsprechender Diazoni - umverbindungen zugänglich. The phenols are accessible by "boiling" appropriate diazonium compounds.
IVδ mit R3 = OR'IVδ with R 3 = OR '
Phosphor-haltige Benzoesäureester der Formel ivδ mit R3 = PXRiR2 können durch Umsetzung von Verbindungen der Formel IVδ mit R3=Br, I, OS02CF3 etc. mit geeigneten Phosphonig- säuren bzw. Phosphorigsäuren in Gegenwart eines Übergangsmetallkatalysators, wie Nickel oder Palladium, sowie ggf. einer Base erhalten werden (vgl. z.B. T. Hirao et al . , Synthesis 1981, 56).Phosphorus-containing benzoic acid esters of the formula ivδ with R 3 = PXRiR 2 can be obtained by reacting compounds of the formula IVδ with R 3 = Br, I, OS0 2 CF 3 etc. with suitable phosphonic acids or phosphorous acids in the presence of a transition metal catalyst, such as nickel or palladium, and optionally a base (see, for example, T. Hirao et al., Synthesis 1981, 56).
IVδ mit R3=Br, I,OS02CF3 IVδ with R 3 = Br, I, OS0 2 CF 3
• Phosphor -haltige Benzoesäureester der Formel IVδ mit R3 = Phenyl können durch Reaktion eines entsprechenden Bro- mids oder Iodids der Formel IVδ mit R3 = Br oder I mit einem Phenylbromid oder Phenyliodid, das ggf. substituiert ist, in Gegenwart von Kupfer hergestellt werden, (vgl. Ranta et. al., Synthesis 1974, 9; Goshaer et al . , Russ. Chem. Rev. 1972, 41, 1046)• Phosphorus-containing benzoic acid esters of the formula IVδ with R 3 = phenyl can be reacted by reacting a corresponding bromide or iodide of the formula IVδ with R 3 = Br or I with a phenylbromide or phenyliodide, which is optionally substituted Be produced in the presence of copper (see Ranta et. Al., Synthesis 1974, 9; Goshaer et al., Russ. Chem. Rev. 1972, 41, 1046)
Phosphor -haltige Benzoesäureester der Formel IVδ mit R3 = ggf. sub. Phenyl, ggf. sub. Heterocyclyl können durch Umsetzung von Verbindungen der Formel IVδ mit R3 = Abgangs - gruppe wie Brom, lod, Triflat, Fluorsulfonyloxy etc. mit einem ggf. sub. Phenyl- bzw. Heterocyclyl -Stannan (Stille-Kupplung), einer ggf. sub. Phenyl- bzw. Heterocyclyl -Borverbindung (Suzuki -Kupplung) oder einer ggf. sub. Phenyl- bzw. Heterocyclyl -Zinkverbindung (Negishi- Kupplung) auf an sich be- kante Art und Weise (vgl. Tetrahedron Lett. 1986, 27, 5265) in Gegenwart eines Palladium- oder Nickelkatalysators und gegebenenfalls einer Base erhalten werden.Phosphorus-containing benzoic acid esters of the formula IVδ with R 3 = optionally sub. Phenyl, optionally sub. Heterocyclyl can be reacted with compounds of the formula IVδ with R 3 = leaving group such as bromine, iodine, triflate, fluorosulfonyloxy etc. with a possibly Sub. phenyl or heterocyclyl stannane (Stille coupling), an optionally sub. phenyl or heterocyclyl boron compound (Suzuki coupling) or an optionally sub. phenyl or heterocyclyl zinc compound (Negishi coupling ) can be obtained in a manner known per se (cf. Tetrahedron Lett. 1986, 27, 5265) in the presence of a palladium or nickel catalyst and optionally a base.
IVδ mit R3=Br , I , OS02CF3 etc . IVδ mit R3=Ar'IVδ with R 3 = Br, I, OS0 2 CF 3 etc. IVδ with R 3 = Ar '
Ar' = ggf. sub. Phenyl bzw. Heterocyclyl Met = Sn(Cι-C4-alkyl)3, B(OH)2, ZnBr, ZnCl Phosphor-haltige Benzoesäureester der Formel IVδ mitAr '= optionally sub. Phenyl or heterocyclyl Met = Sn (-CC 4 -alkyl) 3 , B (OH) 2 , ZnBr, ZnCl Phosphorus-containing benzoic acid esters of the formula IVδ with
R3 = ggf. sub. Heterocyclyl können auch erhalten werden, indem der Heterocyclus aus geeigneten Vorstufen aufgebaut wird.R 3 = optionally sub. Heterocyclyl can also be obtained by building the heterocycle from suitable precursors.
Beispielsweise können aus Aldoximen der Formel XIX durch Kondensation mit Aldehyden der Ketonen 1, 2 , 4 -Oxadiazolin-Deri- vate hergestellt werden (vg. z.B. Arch. Phar . 1993, 326, 383-389) .For example, aldoximes of the formula XIX can be used to produce 1, 2, 4 -oxadiazoline derivatives by condensation with aldehydes of the ketones (cf., for example, Arch. Phar. 1993, 326, 383-389).
Die Thioamide der Formel XX sind geeignete Vorprodukte für 2 -Thiazolinyl -Derivate (vgl. z.B. Tetrahedron 1986, 42, 1449-1460) sowie für 2 -Thiazolyl -Derivate (vgl. z.B. Houben- Weyl, "Methoden der organischen Chemie", 4. Auflage, Bd. E5, S. 1268 ff. (1985) .The thioamides of the formula XX are suitable precursors for 2 -thiazolinyl derivatives (see, for example, Tetrahedron 1986, 42, 1449-1460) and for 2 -thiazolyl derivatives (see, for example, Houben-Weyl, "Methods of Organic Chemistry", 4 Edition, Vol. E5, pp. 1268 ff. (1985).
Aus den Carbonsäuren der Formel XXI sind 2 -Oxazolinyl- ,The carboxylic acids of the formula XXI are 2 -oxazolinyl-,
2 -Thiazolinyl- und 2 -Imidazolinyl -Derivate zugänglich (vgl. z.B. Tetrahedron Lett. 1981, 22, 4471-4474).2 -Thiazolinyl and 2 -Imidazolinyl derivatives available (see e.g. Tetrahedron Lett. 1981, 22, 4471-4474).
Nach literaturbekannten Verfahren können aus Carbonsäurehalo- geniden der Formel XXII, wobei Hai für Halogen steht, insbesondere aus Carbonsäurechloriden, 1, 3 -Thiazol-5 (4H) - thion- 2-yl- bzw. 5-Oxo-2-imidazolin-2 -yl-Derivate hergestellt werden (vgl. z.B. Helv. Chim. Acta, 1986, 69, 374-388; Heterocy- cles 1989, 29, 1185-1189).According to processes known from the literature, 1, 3-thiazol-5 (4H) thion-2-yl or 5-oxo-2-imidazolin-2 can be obtained from carboxylic acid halides of the formula XXII, where shark represents halogen, in particular from carboxylic acid chlorides -yl derivatives are produced (see, for example, Helv. Chim. Acta, 1986, 69, 374-388; Heterocycles 1989, 29, 1185-1189).
Weiterhin ist es möglich aus den Carbonsäuren der Formel XXI bzw. den Carbonsäurehalogeniden der Formel XXII 2-Oxazolyl- Derivate herzustellen (vgl. z.B. Heterocyclic Chem. 1991, 28, 17-28) .It is also possible to prepare 2-oxazolyl derivatives from the carboxylic acids of the formula XXI or the carboxylic acid halides of the formula XXII (cf. e.g. Heterocyclic Chem. 1991, 28, 17-28).
Die Umwandlung von Oximen der Formel XXIV in 4, 5-Dihydroiso- xazol-3-yl bzw. Isoxazol- 3 -yl-Derivate kann auf an sich bekannte Weise über die Zwischenstufe der Hydroxamsäurechloride bzw. -bromide erfolgen. Aus letzeren werden in situ Nitril- oxide erzeugt, die mit Alkenen bzw. Alkinen zu den gewünschten Produkten abreagieren (vgl. z.B. Chem. Ber. 1973, 106, 3258-3274). 1,3 -Dipolare Cycloaddition mit Chlorsulfonyliso- cyanat an das in situ gebildete Nitriloxid liefert 1,2,4-Oxa- diazolin-5-on-3-yl-Derivate (vgl. z.B. Heterocycles 1988, 27, 683-685) .The conversion of oximes of the formula XXIV into 4, 5-dihydroisoxazol-3-yl or isoxazol-3-yl derivatives can be carried out in a manner known per se via the intermediate stage of the hydroxamic acid chlorides or bromides. Nitrile oxides are generated from the latter in situ, which react with alkenes or alkynes to give the desired products (see e.g. Chem. Ber. 1973, 106, 3258-3274). 1,3-Dipolar cycloaddition with chlorosulfonyl isocyanate to the nitrile oxide formed in situ gives 1,2,4-oxadiazolin-5-one-3-yl derivatives (cf. e.g. Heterocycles 1988, 27, 683-685).
Die Aldehyde der Formel XXV können über die Zwischenstufe der Semicarbazone in 2 , 4 -Dihydro-1, 2 , 4 - triazol-3 -on-5-yl -Derivate umgewandelt werden (vgl. z.B. J. Heterocyclic Chem. 1986, 23, 881-883) . 2 -Imidazolinyl -Derivate sind aus Benzonitrilen der Formel XXVI nach bekannten Methoden (vgl. z.B. J. Org. Chem. 1987, 52, 1017-1021 herstellbar.The aldehydes of the formula XXV can be converted via the intermediate stage of the semicarbazones into 2,4-dihydro-1,2,4-triazol-3-one-5-yl derivatives (see, for example, J. Heterocyclic Chem. 1986, 23, 881-883). 2 -Imidazolinyl derivatives can be prepared from benzonitriles of the formula XXVI by known methods (cf., for example, J. Org. Chem. 1987, 52, 1017-1021.
Ebenfalls aus den Benzonitrilen der Formel XXVI sind nach bekannten Verfahren 1, 2, 4 -Triazol-3 -yl-Derivate herstellbar (vgl. z.B. J. Chem. Soc. 1954, 3461-3464).1, 2, 4-triazol-3-yl derivatives can also be prepared from the benzonitriles of the formula XXVI (cf. e.g. J. Chem. Soc. 1954, 3461-3464).
Die Aldehyde XXV lassen sich durch Wittig-Reaktion mit Phos- phonium- Salzen (Ph) 3P+CH2COR*χ- auf an sich bekannte Art und Weise (J. March, "Advanced Organic Chemistry", 3. Auflage, S. 864 ff., Wiley-Interscience Publication, 1985) zu α,ß-un- gesättigen Ketonen XXVII umsetzen. Durch Reaktion mit Hydro- xylamin erhält man daraus die entsprechenden Oxime, die mit- tels oxidativer Cyclisierung in die 5 -Isoxazolyl -Derivate übergeführt werden können (J. Am. Chem. Soc. 1972, 94, 9128) (die Bedeutung von R* entspricht somit der Bedeutung eines Restes durch den Heterocyclyl substituiert sein kann) .The aldehydes XXV can be prepared in a manner known per se by means of the Wittig reaction with phosphonium salts (Ph) 3 P + CH 2 COR * χ- (J. March, "Advanced Organic Chemistry", 3rd edition, p 864 ff., Wiley-Interscience Publication, 1985) to convert α, β-unsaturated ketones XXVII. Reaction with hydroxylamine gives the corresponding oximes, which can be converted into the 5-isoxazolyl derivatives by means of oxidative cyclization (J. Am. Chem. Soc. 1972, 94, 9128) (the meaning of R * thus corresponds to the meaning of a radical by which heterocyclyl can be substituted).
Ebenso können die Aldehyde XXV mit Alkoxymethylphosphonium- salzen auf an sich bekannte Weise (J. March, "Advanced Organic Chemistry", 3. Auflage, S. 864 ff., Wiley-Interscience Publication, 1985) zu den entsprechenden Enolethern übergeführt werden. Spaltung dieser Enolether in Analogie zu lite- raturbekannten Verfahren führt den Acetaldehyd-Derivaten XXVIII. Diese können durch Bro ierung in α- Position zu den α-Bromacetaldehyd-Abkömmlingen umgesetzt werden (Tetrahedron Lett. 1988, 29, 5893), welche durch Cyclisierung mit Amiden, Thioamiden und Amidinen Oxazole, Thiazole und Imida- zole liefern. Weiterhin können die Acetaldehyd-DerivateLikewise, the aldehydes XXV with alkoxymethylphosphonium salts can be converted to the corresponding enol ethers in a manner known per se (J. March, "Advanced Organic Chemistry", 3rd edition, pp. 864 ff., Wiley-Interscience Publication, 1985). Cleavage of these enol ethers in analogy to methods known from the literature leads to the acetaldehyde derivatives XXVIII. These can be converted into the α-bromoacetaldehyde derivatives by bro ating in the α-position (Tetrahedron Lett. 1988, 29, 5893), which, by cyclization with amides, thioamides and amidines, give oxazoles, thiazoles and imidazoles. Furthermore, the acetaldehyde derivatives
XXVIII mit Dimethylformamidimethylacetal in entsprechende En- amine überführt werden, die dann mit Hydroxylaminen bzw. Hy- drazinen zu Isoxazolen bzw. Pyrazolen überführt werden können .XXVIII with dimethylformamidimethylacetal are converted into corresponding enamines, which can then be converted to isoxazoles or pyrazoles with hydroxylamines or hydrazines.
Weiterhin können die Aldehyde XXV mittels Aldolreaktion mit Ketonen in Hydroxyketon-Derivate übergeführt werden. Anschließende Oxidation führt zu 1, 3 -Diketonen, die mit Hydro- xylamin, Hydrazinen oder Amidinen zu Isoxazolen, Pyrazolen oder Pyrimidinen überführt werden können.Furthermore, the aldehydes XXV can be converted into hydroxyketone derivatives by means of an aldol reaction with ketones. Subsequent oxidation leads to 1,3-diketones which can be converted to isoxazoles, pyrazoles or pyrimidines using hydroxylamine, hydrazines or amidines.
Ebenso können die Aldehyde XXV nach literaturbekannten Methoden (Houben-Weyl, "Methoden der organischen Chemie", 4. Auflage, Bd. E14b) in die entsprechenden Diazoverbindungen XXIX übergeführt werden. 1,3-dipolare Cycloaddition an Alkene bzw. Alkine und anschließende Isomerisierung führt zu Pyrazolinen bzw. Pyrazolen.Likewise, the aldehydes XXV can be converted into the corresponding diazo compounds XXIX by methods known from the literature (Houben-Weyl, "Methods of Organic Chemistry", 4th Edition, Volume E14b). 1,3-dipolar cycloaddition on alkenes or Alkynes and subsequent isomerization lead to pyrazolines or pyrazoles.
Der Aldehyd XXV kann in Analogie zu literaturbekannten Verfahren, z.B. aus der entsprechenden Methylverbindung XXX durch Bromierung, beispielsweise mit N-Bromsuccinimid oder 1, 3-Dibrom-5, 5 -dimethylhydantoin, und anschließende Oxidation dargestellt werden (vgl. Synth. Commun. 1992, 22, 1967-1971).The aldehyde XXV can be used analogously to processes known from the literature, e.g. from the corresponding methyl compound XXX by bromination, for example with N-bromosuccinimide or 1, 3-dibromo-5, 5-dimethylhydantoin, and subsequent oxidation (cf. Synth. Commun. 1992, 22, 1967-1971).
Die Oxime der Formel XXIV erhält man vorteilhaft dadurch, daß man in an sich bekannter Weise Aldehyde der Formel XXV mit Hydroxylamin umsetzt (vgl. J. March, "Advanced Organic Chemistry", 3. Auflage, S. 805-806, Wiley, New York, 1985).The oximes of formula XXIV are advantageously obtained by reacting aldehydes of formula XXV with hydroxylamine in a manner known per se (cf. J. March, "Advanced Organic Chemistry", 3rd edition, pp. 805-806, Wiley, New York, 1985).
Die Umwandlung der Oxime XXIV in die Nitrile XXVI kann ebenfalls nach an sich bekannten Verfahren erfolgen (vgl. J. March, "Advanced Organic Chemistry", 3. Auflage, S. 931-932, Wiley, New York, 1985).The conversion of the oxime XXIV into the nitrile XXVI can also be carried out according to methods known per se (cf. J. March, "Advanced Organic Chemistry", 3rd edition, pp. 931-932, Wiley, New York, 1985).
Die Nitrile der Formel XXVI können auf an sich bekannte Art und Weise mit Hydroxylamin in die entsprechenden Ald- oxime XIX, mit Schwefelwasserstoff in die Thioamide XX überführt werden bzw. zu den Carbonsäuren XXI verseift werden. Letztere können auch durch Oxidation aus den Aldehyden XXV erhalten werden (vgl. J. March, "Advanced Organic Chemistry", 3. Auflage, S. 629 ff., Wiley, New York, 1985).The nitriles of the formula XXVI can be converted in a manner known per se with hydroxylamine into the corresponding aldoximes XIX, with hydrogen sulfide into the thioamides XX or can be saponified to give the carboxylic acids XXI. The latter can also be obtained by oxidation from aldehydes XXV (cf. J. March, "Advanced Organic Chemistry", 3rd edition, p. 629 ff., Wiley, New York, 1985).
Die Säurehalogenide XXII können in Analogie zu den Standart - verfahren aus den entsprechenden Carbonsäuren der Formel XXI erhalten werden. The acid halides XXII can be obtained analogously to the standard processes from the corresponding carboxylic acids of the formula XXI.
324 Die Phosphor-haltigen Verbindungen der Formel IVδ sind durch Reaktion von Verbindungen der Formel XXXII mit L5 = Brom, lod, Triflat und einer entsprechend substituierten Phospho- rigsäure oder Phosphonigsäure in Gegenwart eines Übergangsmetallkatalysators, wie Nickel oder Palladium, sowie gegebenenfalls einer Base zugänglich (vgl. z.B. T. Hirao et al., Syn- thesis 1981, 56.)324 The phosphorus-containing compounds of the formula IVδ can be obtained by reacting compounds of the formula XXXII with L 5 = bromine, iodine, triflate and a correspondingly substituted phosphoric acid or phosphonous acid in the presence of a transition metal catalyst, such as nickel or palladium, and optionally a base ( see e.g. T. Hirao et al., Synthesis 1981, 56.)
L5=Br, I, OS02CF3 XXXII IVδL 5 = Br, I, OS0 2 CF 3 XXXII IVδ
Die Verbindungen der Formel XXXII mit L5 = Br, I werden erhalten aus den entsprechenden Nitroverbindungen durch Reduktion der Nitrogruppe und anschließende Sandmeyer-Reaktion. Die Verbindungen der Formel XXXII mit L5=OS02CF3 können durch Umsetzung des entsprechenden Phenols mit Trifluormethylsul- fonsäurechlorid, -anhydrid erhalten werden.The compounds of formula XXXII with L 5 = Br, I are obtained from the corresponding nitro compounds by reduction of the nitro group and subsequent Sandmeyer reaction. The compounds of formula XXXII with L 5 = OS0 2 CF 3 can be obtained by reacting the corresponding phenol with trifluoromethylsulfonic acid chloride, anhydride.
Ebenso können die Verbindungen der Formel IVδ mit R!,R2 = Cι-C6-Alkoxy, Cι-C6 -Aikylthio, Cι-C6 -Alkylamino etc. durch Umseztzung von nucleophil substituierbaren Phosphor- Verbindungen der Formel IVδ mit L' , L" = Abgangsgruppe, wie Halogen, Cι-C6 -Alkoxy etc. mit geeigneten Alkoholen, A inen oder Mercaptanen, ggf. in Gegenwart einer Base, erhalten werden (vgl. z.B. L.J. Kaplan, J.Org. Chem. 1979, 44, 2226; Hou- ben-Weyl, "Methoden der organischen Chemie", Bd. XII/1, S. 423 ff.; R.Z. Greenley et al., J. Org . Chem. 1964, 29, 1009) . Likewise, the compounds of formula IVδ with R ! , R 2 = -C 6 -alkoxy, -C-C 6 -alkylthio, -C-C 6 -alkylamino etc. by reacting nucleophilically substitutable phosphorus compounds of the formula IVδ with L ', L "= leaving group, such as halogen, Cι -C 6 -alkoxy etc. with suitable alcohols, amines or mercaptans, optionally in the presence of a base (see, for example, LJ Kaplan, J.Org. Chem. 1979, 44, 2226; Houben-Weyl, "Methods of Organic Chemistry", Vol. XII / 1, p. 423 ff .; RZ Greenley et al., J. Org. Chem. 1964, 29, 1009).
IVδ mit Ri , R =Cι -C6 - Alkoxy, Cι -C6 -Alkylthio, Cι -C6 -Al -IVδ with R i , R = -C 6 -C alkoxy, -C -C 6 alkylthio, -C -C 6 -Al -
IVδ mit L' ,L"=Abgangsgruppe kylaminoIVδ with L ', L "= leaving group kylamino
Verbindungen der Formel IVδ mit L', L" = Halogen können durch Reaktion von Verbindungen der Formel IVδ mit R1, R2 = OCH3 mit Halogenierungsmitteln erhalten werden, (vgl. z.B. W. Althoff et al., Chem. Ber. 1978, 111, 1845).Compounds of the formula IVδ with L ', L "= halogen can be obtained by reacting compounds of the formula IVδ with R 1 , R 2 = OCH 3 with halogenating agents (see, for example, W. Althoff et al., Chem. Ber. 1978 , 111, 1845).
Als Halogenierungsmittel kommen u.a. Phosgen, Thionylchlorid und Thionylbromid in Betracht.Halogenating agents include Phosgene, thionyl chloride and thionyl bromide into consideration.
Weiterhin sind Verbindungen der Formel IVß durch Oxidation von Verbindungen der Formel XXXIII zugänglich.Compounds of the formula IVß are also accessible by oxidation of compounds of the formula XXXIII.
Oxidationoxidation
XXXIII XXXIII
Geeignete Oxidationsmittel sind z.B. Kaliumpermanganat, (vgl. z.B. Houben Weyl, "Methoden der Organischen Chemie", Bd. IV/la, 1981, sowie Bd. VIII, 1952; E.I. Bengtsson, Acta Chem. Scand. 1953, 7, 774), Chrom (VI) -Verbindungen (vgl. z.B. A.W. Singer et al., Org. Synth. Coll. Vol. III 1955, 740) oder Luftsauerstoff in Gegenwart eines Katalysators wie z.B. Kobalt oder Mangan (vgl. z.B. A.S. Hay et al., Can. J. Chem. 1965, 43, 1306).Suitable oxidizing agents are e.g. Potassium permanganate (see, for example, Houben Weyl, "Methods of Organic Chemistry", vol. IV / la, 1981, and vol. VIII, 1952; EI Bengtsson, Acta Chem. Scand. 1953, 7, 774), chromium (VI) Compounds (see, for example, AW Singer et al., Org. Synth. Coll. Vol. III 1955, 740) or atmospheric oxygen in the presence of a catalyst such as, for example Cobalt or manganese (see e.g. A.S. Hay et al., Can. J. Chem. 1965, 43, 1306).
Die Verbindungen der Formel XXXIII sind durch Reaktion von metallorganischen Verbindungen der Formel XXXIV (mit Met'=Li, Mg) mit Phosphorverbindungen, die nucleophil ersetzbare Gruppen tra- gen (L = Halogen, wie CI, Br, Alkoxy etc.) erhältlich (vgl. z.B. A. Berger et al . , J. Org. Chem. 1951, 16, 1250; M. Sander, Chem. Ber. 1960, 93, 1220) . The compounds of the formula XXXIII can be obtained by reacting organometallic compounds of the formula XXXIV (with Met '= Li, Mg) with phosphorus compounds which carry nucleophilically replaceable groups (L = halogen, such as CI, Br, alkoxy etc.) (cf. e.g. A. Berger et al., J. Org. Chem. 1951, 16, 1250; M. Sander, Chem. Ber. 1960, 93, 1220).
XXXIV XXXIIIXXXIV XXXIII
Ebenso können diese Verbindungen erhalten werden durch Oxidation der entsprechenden Phosphor- III -Verbindungen, die analog zu der oben aufgeführten Reaktion hergestellt werden können.These compounds can also be obtained by oxidation of the corresponding phosphorus III compounds, which can be prepared analogously to the reaction listed above.
Oxidation oxidation
XXXIVXXXIV
XXXIII mit X = 0XXXIII with X = 0
Als Oxidationsmittel eignen sich z.B. Wasserstoffperoxid, Per- oxyessigsäure etc.Suitable oxidizing agents are e.g. Hydrogen peroxide, peroxyacetic acid etc.
Weiterhin können die Verbindungen der Formel XXXIII (mit R2=Cι-C6 -Alkoxy, Cι-C6-Alkyl, C2 -C6 -Alkenyl, C2-C6 -Alkinyl etc.) durch Umsetzung einer Phosphor-Verbindung der Formel XXXV mit einem Alkylhalogenid (Arbuzow-Reaktion) erhalten werden. Can Furthermore, the compounds of Formula XXXIII (with R 2 = Cι-C 6 -alkoxy, C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl etc.) by reacting a phosphorus compound of the formula XXXV can be obtained with an alkyl halide (Arbuzow reaction).
XXXV XXXIII mit R2=Cι-C6 -Alkoxy, Ci-Cβ -Alkyl, C2-C6 -Alkenyl, C2-C6 -Alkinyl etc.XXXV XXXIII where R 2 = Cι-C 6 alkoxy, Ci-Cβ alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl etc.
Als Alkylhalogenide kommen bevorzugt die entsprechenden Bromide und lodide in Betracht (vgl. z.B. B.A. Arbuzow, Pure Appl. Chem. 1964, 9, 307; G.M. Kosolapoff, Org. React. 1951, 6, 273). Suitable alkyl halides are preferably the corresponding bromides and iodides (cf., for example, BA Arbuzow, Pure Appl. Chem. 1964, 9, 307; GM Kosolapoff, Org. React. 1951, 6, 273).
Im Allgemeinen ist es möglich auf einer geeigneten Stufe der Reaktionssequenz der Darstellung der Verbindungen der Formel I den Rest R3 einzuführen bzw. aufzubauen, wobei diese Reaktion voran- stehend geschildert sind oder in Analogie zu bekannten Verfahren durchgeführt werden können. In general, it is possible to introduce or build up the radical R 3 at a suitable stage in the reaction sequence for the preparation of the compounds of the formula I, this reaction being described above or can be carried out in analogy to known processes.
Ebenso kann es in Betracht kommen die Abfolge der Reaktionsschritte zu verändern.It can also be considered to change the sequence of the reaction steps.
Weiterhin können auf einer geeigneten Stufe der Reaktionssequenz die Substituenten Ri und R2 modifiziert werden. Beispielsweise können die Reste R1, R2 = Cι-C6-Alkoxy durch Reaktion mit organo- metallischen Verbindungen in R1, R2 = Cι-C6-Alkyl, C2-C6 -Alkenyl, C2-C6-Alkinyl etc. übergeführt werden. Als Organometallreagentien kommen hier entsprechende Organolithium- oder Organomagnesiumver- bindungen in Betracht (vgl. z.B. Houben-Weyl, "Methoden der Organischen Chemie", Bd. E. 2, S. 38f., Wiley, New York).Furthermore, the substituents R i and R 2 can be modified at a suitable stage of the reaction sequence. For example, the radicals R 1, R 2 can = Cι-C 6 alkoxy by reaction with organo-metallic compounds in R 1, R 2 = Cι-C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 -Alkynyl etc. are transferred. Corresponding organolithium or organomagnesium compounds can be considered as organometallic reagents (cf., for example, Houben-Weyl, "Methods of Organic Chemistry", Vol. E. 2, pp. 38f., Wiley, New York).
Die Phosphor -haltigen Benzoesäurederivate der Formel IVThe phosphorus-containing benzoic acid derivatives of the formula IV
sind neu, wobei die Variablen folgende Bedeutung haben:are new, the variables have the following meaning:
X Sauerstoff oder Schwefel;X oxygen or sulfur;
Ri,R2 Wasserstoff, Cι-C6 -Alkyl, C2 -C6 -Alkenyl, C2-C6 -Alkinyl , Cι-C6 -Alkoxy, C3 -Cö-Alkenyloxy, C3-C6-Alkinyloxy, Mercapto, Cι-C6-Alkylthio, C3-C6-Alkenylthio, C3-C6-Alki- nylthio, Amino, Cι-C6 -Alkylamino, Di-(Cι-C6- alkyDamino, (Ca. -C6 -Alkoxy) (Ci-Cβ-alkyl) -amino, (C3-C6- Alkenyl) (Cι-C6 -alkyl) amino, (C3-C6-Alkinyl) (Cι-C6-al- kyDamino, Di (C3-C6-alkenyl) amino oder Di- (C3-C6-alki- nyl) amino, wobei die genannten Alkyl-, Alkenyl- oder Alkinylreste partiell oder vollständig halogeniert sein können und/oder eine bis drei der folgenden Gruppen tragen können: Nitro, Cyano, C1-C4 -Alkoxy, C1-C4 -Aikylthio, C1-C4-AI- kylsulfinyl, C1-C4 -Alkylsulfonyl, Di(Cι-C4-al- kyl) -amino, C1-C4 -Alkylcarbonyl, C1-C4 -Alkoxycarbonyl, Phenyl oder Heterocyclyl, wobei die beiden letztgenannten Reste seinerseits partiell oder vollständig halogeniert sein können und/oder eine bis drei der foglenden Gruppen tragen können: Nitro, Cyano, C1-C4 -Alkyl, C1-C4 -Halogenalkyl,R i, R 2 are hydrogen, C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, Cι-C 6 -alkoxy, C 3 -C ö alkenyloxy, C 3 -C 6 -Alkynyloxy, mercapto, -C-C 6 -alkylthio, C 3 -C 6 -alkenylthio, C 3 -C 6 -alkynylthio, amino, Cι-C 6 -alkylamino, di- (-Cι-C 6 - alkyDamino, ( . Ca -C 6 alkoxy) (Ci-Cβ-alkyl) amino, (C 3 -C 6 - alkenyl) (Cι-C6 alkyl) amino, (C 3 -C 6 alkynyl) (Cι-C 6 -alkyDamino, di (C 3 -C 6 -alkenyl) amino or di- (C 3 -C 6 -alkynyl) amino, where the alkyl, alkenyl or alkynyl radicals mentioned can be partially or completely halogenated and / or can carry one to three of the following groups: nitro, cyano, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkyl sulfyl, C 1 -C 4 alkyl sulfonyl, di (Cι-C 4 -AL- alkyl) amino, C 1 -C 4 alkylcarbonyl, C 1 -C 4 alkoxycarbonyl, Phenyl or heterocyclyl, where the latter two radicals can in turn be partially or completely halogenated and / or can carry one to three of the following groups: nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl,
C1-C4 -Alkoxy, C1-C4 -Halogenalkoxy oder C1-C4-Alkoxycarbonyl ;C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy or C 1 -C 4 alkoxycarbonyl;
Phenoxy, das partiell oder vollständig halogeniert sein kann und/oder eine bis drei der folgenden Gruppen tragen kann:Phenoxy, which can be partially or completely halogenated and / or can carry one to three of the following groups:
Nitro, Cyano, C1-C4 -Alkyl, C1-C4 -Halogenalkyl, C1-C4 -Alkoxy, C1-C4 -Halogenalkoxy oder C1-C4-Alkoxycarbonyl ; oderNitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy or C 1 -C 4 alkoxycarbonyl; or
R und R2 bilden gemeinsam eine -0- (CH2)m-0- , -0- (CH2)m-S- , -S- (CH2)m-S-, -NR5- (CH2)m-NR5-, -0- (CH2) m-NR5- , -S- (CH2)m-NR5-, -(CH2)n-0-, - (CH2)n-S- oder - (CH2)n-NR5-Kette aus, die einen bis drei Reste aus folgender Gruppe tragen kann:R and R 2 together form a -0- (CH 2 ) m -0-, -0- (CH 2 ) m -S-, -S- (CH 2 ) m -S-, -NR 5 - (CH 2 ) m -NR 5 -, -0- (CH 2 ) m -NR 5 -, -S- (CH 2 ) m -NR 5 -, - (CH 2 ) n -0-, - (CH 2 ) n - S or - (CH 2 ) n -NR 5 chain, which can carry one to three radicals from the following group:
Halogen, Cyano, C1-C4 -Alkyl, C1-C4-Halogenalkyl, C1-C4 -Alkoxy, C1-C4 -Alkoxycarbonyl oder Phenyl, das unsubstituiert ist oder partiell oder vollständig haloge- niert ist und/oder eine bis drei der folgenden Gruppen tragen kann:Halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkoxycarbonyl or phenyl, which is unsubstituted or partially or completely halogenated and / or can carry one to three of the following groups:
Nitro, Cyano, Cι-C -Alkyl, C!-C -Halogenalkyl, Cχ-C4- Alkoxy, C1-C4 -Halogenalkoxy oder Ci-C4-Alkoxycarbonyl ;Nitro, cyano, -CC alkyl, C ! -C -haloalkyl, Cχ-C 4 - alkoxy, C 1 -C 4 -haloalkoxy or Ci-C 4 -alkoxycarbonyl;
oderor
Ri und R2 bilden gemeinsam eine - (CH2)p-Kette, die durch Sauerstoff, Schwefel oder NR5 unterbrochen sein kann und/ oder einen bis drei Reste aus folgender Gruppe tragen kann :Ri and R 2 together form a - (CH 2 ) p chain, which can be interrupted by oxygen, sulfur or NR 5 and / or can carry one to three radicals from the following group:
Halogen, Cyano, Cι-C4-Alkyl, C1-C4 -Halogenalkyl, C1-C4 -Alkoxy, C1-C4 -Alkoxycarbonyl oder Phenyl, das unsubstituiert ist oder partiell oder vollständig halogeniert ist und/oder eine bis drei der folgenden Gruppen tragen kann:Halogen, cyano, C 1 -C 4 -alkyl, C1-C4-haloalkyl, C1-C 4 -alkoxy, C 1 -C 4 -alkoxycarbonyl or phenyl, which is unsubstituted or partially or completely halogenated and / or one to three of the following Groups can carry:
Nitro, Cyano, Cι-C -Alkyl, C1-C4-Halogenalkyl, C1-C4-AI- koxy, C1-C4 -Halogenalkoxy oder Ci -C4-Alkoxycarbonyl;Nitro, cyano, C alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 -AI- koxy, C 1 -C 4 -haloalkoxy or Ci-C4 alkoxycarbonyl;
R3 Cyano, Halogen, Cι-C6 -Alkyl, Cι-C6-Halogenalkyl, Ci-Ce-Al oxy-Ci-Cδ-alkyl, Ci -C6-Halogenalkoxy-Ci -C6 - al - kyl, Cι-C6-Alkylthio-Cι-C6-alkyl, Cι-C6-Alkylsulfi- nyl -Ci-C6 -alkyl , Ci -C6-Alkylsulfonyl -Ci -C6 -alkyl , Ci-Cδ-Alkylcarbonyl, Ci-Cβ-Alkoxy, CI-CÖ -Halogenalkoxy, Cι-C6-Alkylthio, Cι-C6- Halogenalkylthio, Cι-C6-Alkylsul- finyl, Ci-Cβ -Halogenalkylsulfinyl, Cι-C6 -Alkylsulfonyl, Ci-Cβ-Halogenalkylsulfonyl, Aminosulfonyl, Cι-C6-Alky- laminosulfonyl, Di- (Cι-C6- alkyl) aminosulfonyl,R 3 cyano, halogen, -CC 6 -alkyl, -C-C 6 -haloalkyl, Ci-Ce-Al oxy-Ci-C δ -alkyl, Ci -C 6 -haloalkoxy-Ci -C 6 - al - kyl, Cι-C 6 -alkylthio-Cι-C 6 -alkyl, C 6 -C -Alkylsulfi- nyl-C 6 alkyl, Ci-C6 alkylsulfonyl -C -C 6 alkyl, Ci-C δ- alkylcarbonyl, Ci-Cβ-alkoxy, CI-C Ö -haloalkoxy, Cι-C 6 -alkylthio, Cι-C 6 - haloalkylthio, Cι-C 6 -alkylsulfinyl, Ci-Cβ -haloalkylsulfinyl, Cι -C 6 -alkylsulfonyl, Ci-Cβ-haloalkylsulfonyl, aminosulfonyl, -C-C 6 -alkyl-laminosulfonyl, di- (-C-C 6 -alkyl) aminosulfonyl,
(CI-CÖ -Alkylsulfonyl) amino, (Cι-C6-Halogenalkylsulfo- nyl) amino, N- (Cι-C6-Alkyl) -N- (Cι-C6-alkylsulfonyl) amino, N- (Ci-Cδ-Alkyl) -N- (Ci -C6 -halogenalkylsulfo- nyl) mino, -P(=X)RiR2, Phenyl oder Heterocyclyl, wobei die beiden letztgenannten Reste partiell oder vollständig halogeniert sein können und/oder einen bis drei der folgenden Gruppen tragen können:(CI-C Ö alkylsulfonyl) amino, (Cι-C 6 -Halogenalkylsulfo- nyl) amino, N- (Cι-C6 alkyl) -N- (Cι-C 6 alkylsulfonyl) amino, N- (Ci- C δ- alkyl) -N- (Ci-C 6 -haloalkylsulfonyl) mino, -P (= X) R i R 2 , phenyl or heterocyclyl, where the latter two radicals can be partially or completely halogenated and / or one can carry up to three of the following groups:
Nitro, Cyano, Cι-C4-Alkyl, Ci -C4 -Halogenalkyl, C1-C4- Alkoxy, C1-C4 -Halogenalkoxy oder C1-C4 -Alkoxycarbonyl;Nitro, cyano, C 4 alkyl, Ci -C 4 haloalkyl, C 1 -C 4 - alkoxy, C 1 -C 4 -haloalkoxy or C 1 -C 4 alkoxycarbonyl;
R4 Nitro, Cyano, Halogen, Cι-C6-Alkyl, Ci-Cβ-Alkoxy,R 4 nitro, cyano, halogen, -CC 6 alkyl, Ci-Cβ-alkoxy,
Ci-Cö-Alkylthio, Cι-C6 -Alkylsulfinyl oder CI-CÖ-Alkylsulfonyl;Ci-Cö-alkylthio, -C-C 6 alkylsulfinyl or CI-C Ö -alkylsulfonyl;
R5 Wasserstoff, Ci-Cβ-Alkyl, Cι-C6 -Halogenalkyl oder Ci-Cβ -Alkoxy;R 5 is hydrogen, Ci-Cβ-alkyl, -C-C 6 haloalkyl or Ci-Cβ-alkoxy;
1 0 , 1 oder 2 ,-1 0, 1 or 2, -
m 2 , 3 oder 4 ,-m 2, 3 or 4, -
n 3 , 4 oder 5 ;n 3, 4 or 5;
P 4 , 5 oder 6 ;P 4, 5 or 6;
R26 abhydrolysierbarer Rest R 26 hydrolyzable residue
Beispiele für abhydrolysierbare Reste sind Alkoxy-, Phenoxy-, AI kylthio-, Phenylthio-Reste, die ggf. substituiert sein können; Halogenide, Heteroaryl -Reste, die über Stickstoff gebunden sind; Amino-, Imino-Reste, die ggf. sub. sein können etc.Examples of hydrolyzable residues are alkoxy, phenoxy, Al kylthio, phenylthio residues, which may be substituted; Halides, heteroaryl radicals which are bonded via nitrogen; Amino, imino residues, which can possibly be sub etc.
Bevorzugt sind Phosphor -haltige Benzoesäurederivate der Formel IVα mit L2 = Halogen (Ξ≡ IV mit R26 = Halogen) , Hai IVα mit L2 = Halogen Preferred are phosphorus-containing benzoic acid derivatives of the formula IVα with L 2 = halogen (Ξ≡ IV with R 26 = halogen), Shark IVα with L 2 = halogen
wobei die Variablen X, R1 bis R4 und 1 die bei den Verbindungen der Formel IV angegebene Bedeutung haben. Hai steht für Halogen, insbesondere für Chlor oder Brom.where the variables X, R 1 to R 4 and 1 have the meaning given for the compounds of the formula IV. Shark represents halogen, especially chlorine or bromine.
Ebenso bevorzugt sind die Phosphor -haltigen Benzoesäurederivate der Formel IVß (Ξ≡ IV mit R26 = Hydroxy) ,Also preferred are the phosphorus-containing benzoic acid derivatives of the formula IVß (Ξ≡ IV with R 26 = hydroxy),
wobei die Variablen X, R1 bis R4 und 1 die unter den Verbindungen der Formel IV angegebene Bedeutung haben.where the variables X, R 1 to R 4 and 1 have the meaning given under the compounds of the formula IV.
Ebenso bevorzugt sind die Phosphor-haltigen Benzoesäurederivate der Formel IVδ (= IV mit R26 = Ci -C6 -Alkoxy) ,Likewise preferred are the phosphorus-containing benzoic acid derivatives of the formula IVδ (= IV with R 26 = Ci -C 6 alkoxy),
wobei die Variablen X, R1 bis R4 und 1 die bei den Verbindungen der Formel IV angegebene Bedeutung haben undwhere the variables X, R 1 to R 4 and 1 have the meaning given for the compounds of the formula IV and
T CI-CÖ -Alkoxy bedeutet. Die besonders bevorzugten Ausführungsformen der Phosphor-haltigen Benzoesäurederivate der Formel IV, IVα mit L2 = Halogen, IVß und IVÖ in Bezug auf die Variablen X, R1 bis R4 und 1 entsprechen denen der Phosphor-haltigen Benzoyl-Derivate der Formel I.TC I -C Ö -alkoxy means. The particularly preferred embodiments of the phosphorus-containing benzoic acid derivatives of the formula IV, IVα with L 2 = halogen, IVß and IVÖ with respect to the variables X, R 1 to R 4 and 1 correspond to those of the phosphorus-containing benzoyl derivatives of the formula I.
Besonders bevorzugt sind ebenso die Verbindungen der Formel IV, wobei die Variablen folgende Bedeutung haben:The compounds of the formula IV are also particularly preferred, the variables having the following meaning:
Rl,R2 Wasserstoff, Cι-C6-Alkyl, C2-C6-Alkenyl, C2-C6 -Alkinyl, Ci-Cβ-Alkoxy, C3 -C6-Alkenyloxy, C3 -C6 -Alkinyloxy, Mercapto, Cι-C6 -Alkylthio, C3 -Cö-Alkenylthio, C3-C6-Alki- nylthio, Amino, Cι-C6 -Alkylamino oder Di-(Cι-Cδ- alkyl) amino, wobei die genannten Alkyl-, Alkenyl- oder Alkinylreste partiell oder vollständig halogeniert sein können und/oder eine bis drei der folgenden Gruppen tragen können:Rl, R 2 is hydrogen, -CC 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, Ci-Cβ-alkoxy, C 3 -C 6 alkenyloxy, C 3 -C 6 alkynyloxy , mercapto, Cι-C 6 alkylthio, C 3 -C ö -alkenylthio, C 3 -C 6 -Alki- nylthio, amino, Cι-C 6 -alkylamino or di- (Cι-C δ - alkyl) amino, wherein the alkyl, alkenyl or alkynyl radicals mentioned can be partially or completely halogenated and / or can carry one to three of the following groups:
Nitro, Cyano, C1-C4 -Alkoxy, C1-C4 -Aikylthio, C1-C4-Alkylsulfonyl, Di (C1-C4-alkyl) -amino, Cι-C -Alkylcarbo- nyl, C1-C4 -Alkoxycarbonyl, Phenyl oder Heterocyclyl, wobei die beiden letztgenannten Reste seinerseits partiell oder vollständig halogeniert sein können und/oder eine bis drei der foglenden Gruppen tragen können: Nitro, Cyano, C1-C4 -Alkyl, C1-C4 -Halogenalkyl, Cι-C4-Alkoxy, C1-C4 -Halogenalkoxy oder C1-C4 -Alkoxycar- bonyl;Nitro, cyano, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfonyl, di (C 1 -C 4 alkyl) amino, C 1 -C 4 alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl, phenyl or heterocyclyl, where the latter two radicals in turn can be partially or completely halogenated and / or can carry one to three of the following groups: nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 -haloalkyl, -CC 4 alkoxy, C 1 -C 4 haloalkoxy or C 1 -C 4 alkoxycarbonyl;
Phenoxy, das partiell oder vollständig halogeniert sein kann und/oder eine bis drei der folgenden Gruppen tragen kann: Nitro, Cyano, C1-C4 -Alkyl, C1-C4 -Halogenalkyl,Phenoxy which can be partially or completely halogenated and / or can carry one to three of the following groups: nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl,
C1-C4 -Alkoxy, C1-C4-Halogenalkoxy oder C1-C4 -Alkoxycarbonyl ; oderC 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy or C 1 -C 4 alkoxycarbonyl; or
Ri und R2 bilden gemeinsam eine -0- (CH2)m-0- , -0- (CH2)m-S- , -S- (CH2)m-S-, -NR5- (CH2)m-NR5-, -0- (CH2) m-NR5- oder -S- (CH2)m-NR5-Kette aus, die einen bis drei Reste aus folgender Gruppe tragen kann: Halogen, Cyano, C1-C4 -Alkyl, C1-C4 -Halogenalkyl, C1-C4 -Alkoxy, C1-C4 -Alkoxycarbonyl oder Phenyl, das unsubstituiert ist oder partiell oder vollständig halogeniert ist und/oder eine bis drei der folgenden Gruppen tragen kann: Nitro, Cyano, C1-C4 -Alkyl, C1-C4-Halogenalkyl, C1-C4- Alkoxy, Ci -C4 -Halogenalkoxy oder C1-C4 -Alkoxycarbonyl; R3 Cyano, Halogen, Cι-C6 -Alkyl, Cι-C6 -Halogenalkyl,R i and R 2 together form a -0- (CH 2 ) m -0-, -0- (CH 2 ) m -S-, -S- (CH 2 ) m -S-, -NR 5 - (CH 2 ) m -NR 5 -, -0- (CH 2 ) m -NR 5 - or -S- (CH 2 ) m -NR 5 chain, which can carry one to three radicals from the following group: halogen, cyano , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkoxycarbonyl or phenyl which is unsubstituted or partially or fully halogenated and / or one to three of the following groups: nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, Ci -C 4 haloalkoxy or C 1 -C 4 alkoxycarbonyl; R 3 is cyano, halogen, Cι-C 6 -alkyl, C 6 haloalkyl,
Cι-C6-Alkylcarbonyl, C3.-C6 -Alkoxy, Ci-Cβ -Halogenalkoxy, Cx-Cö-Alkylthio, C;ι.-C6-Halogenalkylthio, Cι-C6-Alkylsul- finyl, Cι-C6 -Halogenalkylsulfinyl, Cι-C6 -Alkylsulfonyl, Cι-C6 -Halogenalkylsulfonyl, -P(=X)R!R2, Phenyl oder Heterocyclyl, wobei die beiden letztgenannten Reste partiell oder vollständig halogeniert sein können und/oder einen bis drei der folgenden Gruppen tragen können: Nitro, Cyano, Cι-C4-Alkyl, C1-C4 -Halogenalkyl, C!-C - Alkoxy, C1-C4 -Halogenalkoxy oder C1-C4 -Alkoxycarbonyl;Cι-C 6 alkylcarbonyl, C 3 -C 6 alkoxy, Ci-Cβ haloalkoxy, Cx-C ö alkylthio, C; ι.-C6 haloalkylthio, Cι-C 6 -Alkylsul- finyl, Cι- C 6 -haloalkylsulfinyl, -C-C 6 -alkylsulfonyl, Cι-C 6 -haloalkylsulfonyl, -P (= X) R ! R 2, phenyl or heterocyclyl, where the two last-mentioned radicals to be partially or fully halogenated and / or may carry one to three of the following groups: nitro, cyano, C 4 alkyl, C 1 -C 4 haloalkyl, C ! -C - alkoxy, C 1 -C 4 haloalkoxy or C 1 -C 4 alkoxycarbonyl;
R4 Nitro, Cyano, Halogen, C!-C6-Alkyl, Cι-C6-Alkoxy,R 4 nitro, cyano, halogen, C ! -C 6 alkyl, -CC 6 alkoxy,
Cι-C6-Alkylthio, Ci -C6 -Alkylsulfinyl oder Cι-C6-Alkyl- sulfonyl;C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl or C 1 -C 6 alkyl sulfonyl;
R5 Wasserstoff, Cι-C6 -Alkyl, Cι-C6 -Halogenalkyl oder Ci -C6-Alkoxy;R 5 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl or C 1 -C 6 -alkoxy;
1 0,1 oder 2 ;1 0.1 or 2;
m 2,3 oder 4 ;m 2, 3 or 4;
R26 abhydrolysierbarer Rest.R 26 hydrolyzable residue.
Insbesondere bevorzugt sind die Verbinduntgen der Formel IV, wobei die Variablen folgende Bedeutung haben:The compounds of the formula IV are particularly preferred, the variables having the following meaning:
RX,R2 Wasserstoff, Cι-C6 -Alkyl, Cι-C6 -Alkoxy oder Cι-C6-Aikylthio, wobei die genannten Alkylreste partiell oder vollständig halogeniert sein können und/oder eine bis drei der folgenden Gruppen tragen können: Nitro, Cyano, C1-C4 -Alkoxy, Cι-C -Alkylthio, Di (C1-C4 -alkyl) -amino, Cι-C -Alkylcarbonyl oder Ci - C4 -Alkoxycarbonyl ,-R X , R 2 are hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy or C 1 -C 6 -alkylthio, where the alkyl radicals mentioned can be partially or completely halogenated and / or can carry one to three of the following groups: Nitro, cyano, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, di (C 1 -C 4 alkyl) amino, C 1 -C 4 alkylcarbonyl or Ci - C 4 alkoxycarbonyl, -
R3 Cyano, Halogen, Cι-C6-Alkyl, Cι-C6 -Halogenalkyl,R 3 is cyano, halogen, Cι-C 6 -alkyl, C 6 haloalkyl,
Cι-C6 -Alkoxy, Cι-C6 -Halogenalkoxy, Cι-C6 -Aikylthio, Cι-C6-Halogenalkylthio, Ci-Cβ -Alkylsulfinyl, Ci-Cö-Halo- genalkylsulfinyl, Cχ-C6 -Alkylsulfonyl oder Cι-C6-Halo- genalkylsulfonyl;Cι-C 6 -alkoxy, C 6 haloalkoxy, Cι-C 6 -Aikylthio, Cι-C 6 haloalkylthio, Ci-Cβ alkylsulfinyl, Ci-COE-halo genalkylsulfinyl, Cχ-C 6 alkylsulfonyl or Cι -C 6 haloalkylsulfonyl;
1 0; HerStellungsbeispiele:1 0; Manufacturing examples:
1. Synthese von {3 -Chlor-4 - [ (2 -hydroxy-4, 4 -dimethyl-6-oxo-cyclo- hex-1-en-l-yl- ) carbonyl] -phenyl} -phosphonsäurediethylester (Verbindung 3.1)1. Synthesis of {3-chloro-4 - [(2-hydroxy-4,4, -dimethyl-6-oxo-cyclo-hex-1-en-1-yl-) carbonyl] -phenyl} -phosphonic acid diethyl ester (compound 3.1 )
Stufe a) (3-Chlor-4-methyl-phenyl) -phosphonsäurediethylesterStep a) (3-chloro-4-methyl-phenyl) -phosphonic acid diethyl ester
Ein Gemisch aus 32,0 g (0,127 mol) 2 -Chlor-4 -iod- toluol, 17,5 g (0,127 mol) Phosphorigsaurediethylester, 12,8 g (0,127 mol) Triethylamin und 14,7 g (0,0127 mol) Tetrakis- triphenylphosphin- Palladium (0) in 200 ml Acetonitril wurde 5 Stunden unter Rückfluß erhitzt. Nach dem Erkalten rührte man in Wasser ein und extrahierte mit Ethylacetat. Die organische Phase wurde getrocknet, eingeengt und der Rückstand anschließend destilliert. Ausbeute: 23,4 g (70 %) ; farbloses Öl iH-NMR (CDC13) : δ=7,88 (m, IH) ; 7,60 (m, IH) ; 7,52 (m, IH) ; 4,10 (m,4H); 2,40 (s,3H); 1,34 (t, 6H)A mixture of 32.0 g (0.127 mol) of 2-chloro-4-iodotoluene, 17.5 g (0.127 mol) of diethyl phosphate, 12.8 g (0.127 mol) of triethylamine and 14.7 g (0.0127 mol) ) Tetrakis triphenylphosphine palladium (0) in 200 ml of acetonitrile was heated under reflux for 5 hours. After cooling, the mixture was stirred into water and extracted with ethyl acetate. The organic phase was dried and concentrated, and the residue was then distilled. Yield: 23.4 g (70%); colorless oil iH-NMR (CDC1 3 ): δ = 7.88 (m, IH); 7.60 (m, IH); 7.52 (m, IH); 4.10 (m, 4H); 2.40 (s, 3H); 1.34 (t, 6H)
Stufe b) (3 -Chlor-4 -hydroxycarbonyl-phenyl) -phosphonsäurediethylester (Verbindung 6.1)Step b) (3-chloro-4-hydroxycarbonyl-phenyl) -phosphonic acid diethyl ester (compound 6.1)
Zu einer Lösung von 1,0 g (3,81 mmol) des Produktes aus Stufe a) in 5 ml Pyridin gab man bei 80°C portionsweise eine Lösung von 1,76 g (11 'mmol) Kaliumpermanganat in 10 ml Wasser. Nach 6 Stunden Rühren bei Raumtemperatur gab man Sodalösung zu und filtrierte vom Niederschlag ab. Das Filtrat wurde mit Salzsäure angesäuert und mit Ethylacetat extrahiert. Ausbeute: 0,75 g (67%); farbloser Farbstoff iH-NMR (d6-DMSO) δ= 13,8 (bs, IH) ; 7,90 (m, IH) ; 7,75 (m, 2H) ; 4,06 (m,4H) ; 1,25 (t,6H)A solution of 1.76 g (11 ' mmol) of potassium permanganate in 10 ml of water was added in portions to a solution of 1.0 g (3.81 mmol) of the product from stage a) in 5 ml of pyridine at 80 ° C. After stirring for 6 hours at room temperature, sodium carbonate solution was added and the precipitate was filtered off. The filtrate was acidified with hydrochloric acid and extracted with ethyl acetate. Yield: 0.75 g (67%); colorless dye iH-NMR (d 6 -DMSO) δ = 13.8 (bs, IH); 7.90 (m, IH); 7.75 (m. 2H); 4.06 (m, 4H); 1.25 (t, 6H)
Stufe c) {3-Chlor-4- [2 -hydroxy-4, 4 -dimethyl-δ-oxo-cyclo- hex-l-en-l-yl) carbonyl] -phenyl} -phosphonsäurediethyl- esterStep c) {3-chloro-4- [2-hydroxy-4,4,4-dimethyl-δ-oxo-cyclo-hex-1-en-1-yl) carbonyl] -phenyl} -phosphonic acid diethyl ester
Ein Gemisch aus 0,65 g (2,2 mmol) des Produktes der Stufe b) , 0,45 g (2,2 mmol) N,N-Dicyclohexylcarbodiimid und 0,31 g Dimedon in 30 ml Acetonitril wurde über Nacht bei Raumtemperatur gerührt. Anschließend setzte man 0,45 g (4,4 mmol) Triethylamin und 0,2 ml Trimethylsilylcyanid zu und rührte weitere 18 Stunden bei Raumtemperatur. Das Reaktionsgemisch wurde auf je 50 ml Ethylacetat und 2%ige Sodalösung gegeben und filtriert. Die wäßrige Phase wurde mit Diethylether gewaschen und anschließend ein pH-Wert von 4-5 mit Salzsäure eingestellt. Man extrahierte mit Ethylacetat, trocknete die organische Phase und entfernte das Lösungsmittel. Ausbeute: 0,36 g (39 %) ; rotes Öl IH-NMR (CDCI3) : δ= 7,78 (m,2H) ; 7,28 (m, IH) ; 4,12 (m, 4H) ; 2,65 (m,2H) ; 2,32 (m,2H) ; 1,32 (t,6H) ; 1,14 (s,6H) .A mixture of 0.65 g (2.2 mmol) of the product of step b), 0.45 g (2.2 mmol) of N, N-dicyclohexylcarbodiimide and 0.31 g of dimedone in 30 ml of acetonitrile was left overnight at room temperature touched. Then 0.45 g (4.4 mmol) of triethylamine and 0.2 ml of trimethylsilyl cyanide were added and the mixture was stirred at room temperature for a further 18 hours. The reaction mixture was added to 50 ml each of ethyl acetate and 2% sodium carbonate solution and filtered. The aqueous phase was washed with diethyl ether and then a pH of 4-5 was adjusted with hydrochloric acid. The mixture was extracted with ethyl acetate, the organic phase was dried and the solvent was removed. Yield: 0.36 g (39%); red oil IH NMR (CDCI 3 ): δ = 7.78 (m, 2H); 7.28 (m, IH); 4.12 (m, 4H); 2.65 (m. 2H); 2.32 (m, 2H); 1.32 (t, 6H); 1.14 (s, 6H).
2. Synthese von {3 -Chlor-4 - [ (1 -ethyl -5 -hydroxy- lH-pyrazol- 4 -yl- carbonyl] -phenyl}phosphonsäurediethylester (Verbindung 5.1)2. Synthesis of {3-chloro-4 - [(1-ethyl -5-hydroxy-1H-pyrazole-4 -ylcarbonyl] phenyl} phosphonic acid diethyl ester (compound 5.1)
Ein Gemisch von 1,0 g (3,4 mmol) des Produktes aus Synthese 1 Stufe b) 0,71 g (3,4 mmol) N,N-Dicyclohexylcarbodiimid und (0,38 g, 3,4 mmol) 5-Hydroxy- 1-ethylpyrazol wurde bei Raumtemperatur 36 Stunden gerührt. Man gab das Reaktionsgemisch auf je 50 ml Ethylacetat und 2 %ige Sodalösung, trocknete die organische Phase und entfernte das Lösungsmittel. Der Rückstand wurde an Kieselgel mit Cyclohexan/Ethylacetat chromatografiert. Das so er- haltene O-acylierte Produkt (0,36 g) wurde dann in 1,4-Dioxan mit Kaliumcarbonat versetzt und 4 Stunden unter Rückfluß erhitzt. Man gab das Reaktionsgemisch auf Wasser und extrahierte mit Ethylacetat. Die wäßrige Phase wurde einmal mit Diethylether gewaschen, mit Salzsäure auf pH 4 eingestellt und mit Ethylacetat extra - hiert. Man trocknete die organische Phase und entfernte das Lösungsmittel .A mixture of 1.0 g (3.4 mmol) of the product from synthesis 1 stage b) 0.71 g (3.4 mmol) of N, N-dicyclohexylcarbodiimide and (0.38 g, 3.4 mmol) of 5- Hydroxy-1-ethylpyrazole was stirred at room temperature for 36 hours. The reaction mixture was added to 50 ml of ethyl acetate and 2% sodium carbonate solution, the organic phase was dried and the solvent was removed. The residue was chromatographed on silica gel with cyclohexane / ethyl acetate. The O-acylated product (0.36 g) thus obtained was then mixed with potassium carbonate in 1,4-dioxane and heated under reflux for 4 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The aqueous phase was washed once with diethyl ether, adjusted to pH 4 with hydrochloric acid and extracted with ethyl acetate. The organic phase was dried and the solvent was removed.
Ausbeute: 0,17 g; rotes Öl iH-NMR (CDC13): δ= 7,95 (m, IH) ; 7,78 (m, IH) ; 7,55 (m, IH) ,- 7,38 (S,1H); 4,40 (m,2H); 4,13 (m, 4H) ; 1,44 (t,3H); 1,36 (t,6H)Yield: 0.17 g; red oil iH-NMR (CDC1 3 ): δ = 7.95 (m, IH); 7.78 (m, IH); 7.55 (m, IH) - 7.38 (S, 1H); 4.40 (m. 2H); 4.13 (m, 4H); 1.44 (t, 3H); 1.36 (t, 6H)
In den Tabellen 3 bis 7 sind neben den voranstehend beschriebenen Verbindungen der Formel I bzw. IV weitere aufgeführt, die in analoger Weise hergestellt wurden oder herstellbar sind: In addition to the compounds of the formula I or IV described above, tables 3 to 7 list further ones which were prepared or can be prepared in an analogous manner:
ro α> > -Q röro α>> -Q ro
Eπ Tabelle :Eπ Table :
I2a mit X = O; R8, R9 , R10, R12 =H; R7+RH=-CH2-CH2- I2a with X = O; R 8 , R 9 , R 10 , R 12 = H; R 7 + RH = -CH 2 -CH 2 -
Tabelle 5: Table 5:
oO
CDCD
Λ rd EH Tabelle 7: E rd EH Table 7:
Die Verbindungen der Formel I und deren landwirtschaftlich brauchbaren Salze eignen sich sowohl als Isomerengemische als auch in Form der reinen Isomeren - als Herbizide. Die herbiziden Mittel, die Verbindungen der Formel I enthalten, bekämpfen Pflanzenwuchs auf Nichtkulturflächen sehr gut, besonders bei hohen Aufwandmengen. In Kulturen wie Weizen, Reis, Mais, Soja und Baumwolle wirken sie gegen Unkräuter und Schadgräser, ohne die Kulturpflanzen nennenswert zu schädigen. Dieser Effekt tritt vor al- lern bei niedrigen Aufwandmengen auf .The compounds of formula I and their agriculturally useful salts are suitable both as isomer mixtures and in the form of the pure isomers - as herbicides. The herbicidal compositions which contain compounds of the formula I control vegetation very well on non-cultivated areas, especially when high amounts are applied. In crops such as wheat, rice, corn, soybeans and cotton, they act against weeds and grass weeds without significantly damaging the crop plants. This effect occurs above all at low application rates.
In Abhängigkeit von der jeweiligen Applikationsmethode können die Verbindungen der Formel I bzw. sie enthaltenden herbiziden Mittel noch in einer weiteren Zahl von Kulturpflanzen zur Beseitigung unerwünschter Pflanzen eingesetzt werden. In Betracht kommen beispielsweise folgende Kulturen:Depending on the particular application method, the compounds of the formula I or herbicidal compositions comprising them can also be used in a further number of crop plants for eliminating undesired plants. The following crops are considered, for example:
Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica) , Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum,Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea libericaus), Cucumodison , Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum,
(Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium) , Helianthus annuus, Hevea brasiliensis, Hordeum vulgäre, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec, Manihot esculenta, Medicago sativa, Musa spec, Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Seeale cereale, Solanum tuberosum, Sorghum bicolor (s. vulgäre), Theobroma cacao, Trifo- lium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera und Zea mays .(Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgäre, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersica, Musus spec, manus spec, Medicinal specimen, Malus spec. Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarle, Seeale Solanum tuberosum, sorghum bicolor (see vulgar), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.
Darüber hinaus können die Verbindungen der Formel I auch in Kul- turen, die durch Züchtung einschließlich gentechnischer Methoden gegen die Wirkung von Herbiziden tolerant sind, verwandt werden.In addition, the compounds of the formula I can also be used in crops which are tolerant to the action of herbicides by breeding, including genetic engineering methods.
Die Verbindungen der Formel I bzw. die sie enthaltenden herbiziden Mittel können beispielsweise in Form von direkt versprühbaren wäßrigen Lösungen, Pulvern, Suspensionen, auch hochprozentigen wäßrigen, öligen oder sonstigen Suspensionen oder Dispersionen, Emulsionen, Öldispersionen, Pasten, Stäubemitteln, Streumitteln oder Granulaten durch Versprühen, Vernebeln, Verstäuben, Verstreuen oder Gießen angewendet werden. Die Anwendungsformen richten sich nach den Verwendungszwecken; sie sollten in jedem Fall möglichst die feinste Verteilung der erfindungsgemäßen Wirkstoffe gewährleisten.The compounds of the formula I or the herbicidal compositions comprising them can be used, for example, in the form of directly sprayable aqueous solutions, powders, suspensions, including high-strength aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, Scattering agents or granules can be applied by spraying, atomizing, dusting, scattering or pouring. The application forms depend on the purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
Die herbiziden Mittel enthalten eine herbizid wirksame Menge mindestens einer Verbindung der Formel I oder eines landwirtschaftlich brauchbaren Salzes von I und für die Formulierung von Pflan- zenschutzmitteln übliche Hilfsmittel.The herbicidal compositions comprise a herbicidally effective amount of at least one compound of the formula I or an agriculturally useful salt of I and auxiliaries customary for the formulation of crop protection agents.
Als inerte Hilfsstoffe kommen im Wesentlichen in Betracht:The following are essentially considered as inert auxiliaries:
Mineralölfraktionen von mittlerem bis hohem Siedepunkt wie Kerosin und Dieselöl, ferner Kohlenteeröle sowie Öle pflanzlichen oder tierischen Ursprungs, aliphatische, cyclische und aromatische Kohlenwasserstoffe, z.B. Paraffin, Tetrahydronaphthalin, alkylierte Naphthaline und deren Derivate, alkylierte Benzole oder deren Derivate, Alkohole wie Methanol, Ethanol, Propanol, Butanol und Cyclohexanol, Ketone wie Cyclohexanon, stark polare Lösungsmittel, z.B. Amine wie N-Methylpyrrolidon und Wasser.Mineral oil fractions from medium to high boiling point such as kerosene and diesel oil, also coal tar oils as well as oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Paraffin, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes or their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, strongly polar solvents, e.g. Amines such as N-methylpyrrolidone and water.
Wäßrige Anwendungsformen können aus Emulsionskonzentraten, Suspensionen, Pasten, netzbaren Pulvern oder wasserdispergierbaren Granulaten durch Zusatz von Wasser bereitet werden. Zur Herstellung von Emulsionen, Pasten oder Öldispersionen können die Phosphor-haltigen Benzoyl-Derivate der Formel I als solche oder in einem Öl oder Lösungsmittel gelöst, mittels Netz-, Haft-, Dispergier- oder Emulgiermittel in Wasser homogenisiert werden. Es können aber auch aus wirksamer Substanz, Netz-, Haft-,Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water. To prepare emulsions, pastes or oil dispersions, the phosphorus-containing benzoyl derivatives of the formula I, as such or dissolved in an oil or solvent, can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers. However, it can also consist of active substance, wetting, adhesive,
Dispergier- oder Emulgiermittel und eventuell Lösungsmittel oder Öl bestehende Konzentrate hergestellt werden, die zur Verdünnung mit Wasser geeignet sind.Dispersants or emulsifiers and possibly solvents or oil existing concentrates are prepared which are suitable for dilution with water.
Als oberflächenaktive Stoffe kommen die Alkali-, Erdalkali-, Ammoniumsalze von aromatischen Sulfonsäuren, z.B. Lignin-, Phenol-, Naphthalin- und Dibutylnaphthalinsulfonsäure, sowie von Fettsäuren, Alkyl- und Alkylarylsulfonaten, Alkyl-, Laurylether- und Fettalkoholsulfaten, sowie Salze sulfatierter Hexa-, Hepta- und Octadecanolen sowie von Fettalkoholglykolether, Kondensationsprodukte von sulfoniertem Naphthalin und seiner Derivate mit Formaldehyd, Kondensationsprodukte des Naphthalins bzw. der Naphthalinsulfonsäuren mit Phenol und Formaldehyd, Polyoxy- ethylenoctylphenolether, ethoxyliertes Isooctyl-, Octyl- oder Nonylphenol, Alkylphenyl-, Tributylphenylpolyglykolether, Alkyl - arylpolyetheralkohole, Isotridecylalkohol, Fettalkoholethylen- oxid-Kondensate, ethoxyliertes Rizinusöl, Polyoxyethylen- oder Polyoxypropylenalkylether, Laurylalkoholpolyglykoletheracetat, Sorbitester, Lignin-Sulfitablaugen oder Methylcellulose in Betracht.The surface-active substances are the alkali metal, alkaline earth metal and ammonium salts of aromatic sulfonic acids, for example lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa- , Hepta- and octadecanols as well as fatty alcohol glycol ether, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl, octyl or nonylphenyl glycolphenyl, alkylphen - Aryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene or Polyoxypropylene alkyl ether, lauryl alcohol polyglycol ether acetate, sorbitol ester, lignin sulfite waste liquor or methyl cellulose.
Pulver-, Streu- und Stäubemittel können durch Mischen oder gemeinsames Vermählen der wirksamen Substanzen mit einem festen Trägerstoff hergestellt werden.Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
Granulate, z.B. Umhüllungs-, Imprägnierungs- und Homogengranulate können durch Bindung der Wirkstoffe an feste Trägerstoffe hergestellt werden. Feste Trägerstoffe sind Mineralerden wie Kieselsäuren, Kieselgele, Silikate, Talkum, Kaolin, Kalkstein, Kalk, Kreide, Bolus, Löß, Ton, Dolomit, Diatomeenerde, Calcium- und Magnesiumsulfat, Magnesiumoxid, gemahlene Kunststoffe, Dünge- mittel, wie Ammoniumsulfat, Ammoniumphosphat, Ammoniumnitrat, Harnstoffe und pflanzliche Produkte wie Getreidemehl, Baumrinden-, Holz- und Nußschalenmehl, Cellulosepulver oder andere feste Trägerstoffe.Granules, e.g. Coated, impregnated and homogeneous granules can be produced by binding the active ingredients to solid carriers. Solid carriers are mineral soils such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, Ammonium nitrate, ureas and vegetable products such as corn flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
Die Konzentrationen der Verbindungen der Formel I in den anwendungsfertigen Zubereitungen können in weiten Bereichen variiert werden. Im allgemeinen enthalten die Formulierungen etwa von 0,001 bis 98 Gew.-%, vorzugsweise 0,01 bis 95 Gew.-%, mindestens eines Wirkstoffs. Die Wirkstoffe werden dabei in einer Reinheit von 90% bis 100%, vorzugsweise 95% bis 100% (nach NMR- Spektrum) eingesetzt.The concentrations of the compounds of the formula I in the ready-to-use preparations can be varied within a wide range. In general, the formulations contain from about 0.001 to 98% by weight, preferably 0.01 to 95% by weight, of at least one active ingredient. The active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).
Die folgenden Formulierungsbeispiele verdeutlichen die Herstellung solcher Zubereitungen:The following formulation examples illustrate the preparation of such preparations:
I. 20 Gewichtsteile der Verbindung Nr. 3.3 werden in einer Mischung gelöst, die aus 80 Gewichtsteilen alkyliertem Benzol, 10 Gewichtsteilen des Anlagerungsproduktes von 8 bis 10 Mol Ethylenoxid an 1 Mol Ölsäure-N-monoethanolamid, 5 Gewichtsteilen Calciumsalz der Dodecylbenzolsulfonsäure und 5 Gewichtsteilen des Anlagerungsproduktes von 40 Mol Ethylenoxid an 1 Mol Rizinusöl besteht. Durch Ausgießen und feines Verteilen der Lösung in 100000 Gewichtsteilen Wasser erhält man eine wäßrige Dispersion, die 0,02 Gew.-% des Wirkstoffs enthält.I. 20 parts by weight of compound no. 3.3 are dissolved in a mixture consisting of 80 parts by weight of alkylated benzene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight of calcium salt of dodecylbenzenesulfonic acid and 5 parts by weight of Addition product of 40 moles of ethylene oxide with 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and finely distributing it therein, an aqueous dispersion is obtained which contains 0.02% by weight of the active ingredient.
II. 20 Gewichtsteile der Verbindung Nr. 3.3 werden in einer Mischung gelöst, die aus 40 Gewichtsteilen Cyclohexanon,II. 20 parts by weight of compound no. 3.3 are dissolved in a mixture consisting of 40 parts by weight of cyclohexanone,
30 Gewichtsteilen Isobutanol, 20 Gewichtsteilen des Anlage- rungsproduktes von 7 Mol Ethylenoxid an 1 Mol Isooctyl- phenol und 10 Gewichtsteilen des Anlagerungsproduktes von 40 Mol Ethylenoxid an 1 Mol Rizinusöl besteht. Durch Ein- gießen und feines Verteilen der Lösung in 100000 Gewichtsteilen Wasser erhält man eine wäßrige Dispersion, die 0,02 Gew.-% des Wirkstoffs enthält.30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 moles of ethylene oxide and 1 mole of isooctylphenol and 10 parts by weight of the additive of 40 moles of ethylene oxide in 1 mole of castor oil. Through a- pouring and finely distributing the solution in 100,000 parts by weight of water gives an aqueous dispersion which contains 0.02% by weight of the active ingredient.
III. 20 Gewichtsteile der Verbindung Nr. 3.3 werden in einer Mischung gelöst, die aus 25 Gewichtsteilen Cyclohexanon, 65 Gewichtsteilen einer Mineralölfraktion vom Siedepunkt 210 bis 280°C und 10 Gewichtsteilen des Anlagerungs- produktes von 40 Mol Ethylenoxid an 1 Mol Ricinusöl be- steht. Durch Eingießen und feines Verteilen der Lösung in 100000 Gewichtsteilen Wasser erhält man eine wäßrige Dispersion, die 0,02 Gew.-% des Wirkstoffs enthält.III. 20 parts by weight of compound no. 3.3 are dissolved in a mixture consisting of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction with a boiling point of 210 to 280 ° C. and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active ingredient.
IV. 20 Gewichtsteile der Verbindung Nr. 3.3 werden mit 3 Gewichtsteilen des Natriumsalzes der Diisobutylnaphthalin- sulfonsäure, 17 Gewichtsteilen des Natriumsalzes einer Ligninsulfonsäure aus einer Sulfit-Ablauge und 60 Gewichtsteilen pulverförmigem Kieselsäuregel gut vermischt und in einer Hammermühle vermählen. Durch feines Verteilen der Mischung in 20000 Gewichtsteilen Wasser erhält man eine Spritzbrühe, die 0,1 Gew.-% des Wirkstoffs enthält.IV. 20 parts by weight of compound no. 3.3 are mixed well with 3 parts by weight of the sodium salt of diisobutylnaphthalenesulfonic acid, 17 parts by weight of the sodium salt of lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of powdered silica gel and ground in a hammer mill. By finely distributing the mixture in 20,000 parts by weight of water, a spray liquor is obtained which contains 0.1% by weight of the active ingredient.
V. 3 Gewichtsteile der Verbindung Nr. 3.3 werden mitV. 3 parts by weight of compound no
97 Gewichtsteilen feinteiligem Kaolin vermischt. Man erhält auf diese Weise ein Stäubemittel, das 3 Gew.-% des Wirkstoffs enthält.97 parts by weight of finely divided kaolin mixed. In this way, a dust is obtained which contains 3% by weight of the active ingredient.
VI. 20 Gewichtsteile der Verbindung Nr. 3.3 werden mitVI. 20 parts by weight of compound no
2 Gewichtsteilen Calciumsalz der Dodecylbenzolsulfonsäure, 8 Gewichtsteilen Fettalkoholpolyglykolether, 2 Gewichtsteilen Natriumsalz eines Phenol-Harnstoff-Formaldehyd-Kondensates und 68 Gewichtsteilen eines paraffinischen Mineralöls innig vermischt. Man erhält eine stabile ölige Dispersion.2 parts by weight of calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of fatty alcohol polyglycol ether, 2 parts by weight of sodium salt of a phenol-urea-formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil. A stable oily dispersion is obtained.
VII. 1 Gewichtsteil der Verbindung Nr. 3.3 wird in einer Mischung gelöst, die aus 70 Gewichtsteilen Cyclohexanon, 20 Gewichtsteilen ethoxyliertem Isooctylphenol undVII. 1 part by weight of compound no. 3.3 is dissolved in a mixture consisting of 70 parts by weight of cyclohexanone, 20 parts by weight of ethoxylated isooctylphenol and
10 Gewichtsteilen ethoxyliertem Rizinusöl besteht. Man er- hält ein stabiles Emulsionskonzentrat.There are 10 parts by weight of ethoxylated castor oil. A stable emulsion concentrate is obtained.
VIII. 1 Gewichtsteil der Verbindung Nr. 3.3 wird in einer Mischung gelöst, die aus 80 Gewichtsteilen Cyclohexanon und 20 Gewichtsteilen WettolR EM 31 (= nichtionischer Emulgator auf der Basis von ethoxyliertem Rizinusöl) besteht. Man erhält ein stabiles Emulsionskonzentrat. Die Applikation der Verbindungen der Formel I bzw. der herbiziden Mittel kann im Vorauflauf- oder im Nachauflaufverfahren erfolgen. Sind die Wirkstoffe für gewisse Kulturpflanzen weniger verträglich, so können Ausbringungstechniken angewandt werden, bei welchen die herbiziden Mittel mit Hilfe der Spritzgeräte so gespritzt werden, daß die Blätter der empfindlichen Kulturpflanzen nach Möglichkeit nicht getroffen werden, während die Wirkstoffe auf die Blätter darunter wachsender unerwünschter Pflanzen oder die unbedeckte Bodenfläche gelangen (post-directed, lay-by) .VIII. 1 part by weight of compound no. 3.3 is dissolved in a mixture consisting of 80 parts by weight of cyclohexanone and 20 parts by weight of Wettol R EM 31 (= nonionic emulsifier based on ethoxylated castor oil). A stable emulsion concentrate is obtained. The compounds of the formula I or the herbicidal compositions can be applied pre- or post-emergence. If the active ingredients are less compatible for certain crop plants, application techniques can be used in which the herbicidal compositions are sprayed with the aid of sprayers in such a way that the leaves of the sensitive crop plants are not hit wherever possible, while the active ingredients are applied to the leaves of undesirable plants growing below them or the uncovered floor area (post-directed, lay-by).
Die Aufwandmengen an Verbindung der Formel I betragen je nach Bekämpfungsziel, Jahreszeit, Zielpflanzen und WachstumsStadium 0.001 bis 3.0 vorzugsweise 0.01 bis 1.0 kg/ha aktive Substanz (a.S.).The application rates of the compound of the formula I are 0.001 to 3.0, preferably 0.01 to 1.0 kg / ha of active substance (as specified), depending on the control target, the season, the target plants and the growth stage.
Zur Verbreiterung des Wirkungsspektrums und zur Erzielung synergistischer Effekte können die Phosphor-haltigen Benzoyl-Derivate der Formel I mit zahlreichen Vertretern anderer herbizider oder wachstumsregulierender Wirkstoffgruppen gemischt und gemeinsam ausgebracht werden. Beispielsweise kommen als Mischungspartner 1, 2, 4-Thiadiazole, 1, 3 , 4-Thiadiazole, Amide, Aminophosphorsäure und deren Derivate, Aminotriazole, Anilide, Aryloxy-/Heteroaryl - oxyalkansäuren und deren Derivate, Benzoesäure und deren Derivate, Benzothiadiazinone, 2-Aroyl-l, 3-cyclohexandione, Heteroaryl-Aryl-Ketone, Benzylisoxazolidinone, meta-CF3-Phenyl- derivate, Carbamate, Chinolincarbonsäure und deren Derivate, Chloracetanilide, Cyclohexenonoximetherderivate, Diazine, Dichlorpropionsäure und deren Derivate, Dihydrobenzofurane, Dihydrofuran-3-one, Dinitroaniline, Dinitrophenole, Diphenyl- ether, Dipyridyle, Halogencarbonsäuren und deren Derivate, Harnstoffe, 3-Phenyluracile, Imidazole, Imidazolinone, N-Phe- nyl-3 , 4, 5, 6-tetrahydrophthalimide, Oxadiazole, Oxirane, Phenole, Aryloxy- und Heteroaryloxyphenoxypropionsäureester, Phenylessig- säure und deren Derivate, Phenylpropionsaure und deren Derivate, Pyrazole, Phenylpyrazole, Pyridazine, Pyridincarbonsäure und deren Derivate, Pyrimidylether, Sulfonamide, Sulfonylharnstoffe, Triazine, Triazinone, Triazolinone, Triazolcarboxamide und Uracile in Betracht.To broaden the spectrum of activity and to achieve synergistic effects, the phosphorus-containing benzoyl derivatives of the formula I can be mixed with numerous representatives of other herbicidal or growth-regulating active compound groups and applied together. For example, 1, 2, 4-thiadiazoles, 1, 3, 4-thiadiazoles, amides, aminophosphoric acid and their derivatives, aminotriazoles, anilides, aryloxy- / heteroaryl-oxyalkanoic acids and their derivatives, benzoic acid and their derivatives, benzothiadiazinones, 2- Aroyl-l, 3-cyclohexanediones, heteroaryl aryl ketones, benzylisoxazolidinones, meta-CF 3 phenyl derivatives, carbamates, quinolinecarboxylic acid and their derivatives, chloroacetanilides, cyclohexenone oxime ether derivatives, diazines, dichloropropionic acid and their derivatives, dihydrofuran acid and their derivatives, dihydrofuran acid and their derivatives , Dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3, 4, 5, 6-tetrahydrophthalimides, oxadiazoles, oxiranes, phenols, aryloxy- aryloxy- and heteroaryloxyphenoxypropionic acid esters, phenylacetic acid and its derivatives, phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and their de derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxamides and uraciles.
Außerdem kann es von Nutzen sein, die Verbindungen der Formel I allein oder in Kombination mit anderen Herbiziden auch noch mit weiteren Pflanzenschutzmitteln gemischt, gemeinsam auszubringen, beispielsweise mit Mitteln zur Bekämpfung von Schädlingen oder phytopathogenen Pilzen bzw. Bakterien. Von Interesse ist ferner die Mischbarkeit mit Mineralsalzlösungen, welche zur Behebung von Ernährungs- und Spurenelementmängeln eingesetzt werden. Es können auch nichtphytotoxische Öle und Ölkonzentrate zugesetzt werden.It may also be useful to apply the compounds of the formula I, alone or in combination with other herbicides, mixed with other crop protection agents, for example with agents for controlling pests or phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions, which are used to remedy nutritional and trace element deficiencies. It can non-phytotoxic oils and oil concentrates can also be added.
AnwendungsbeispieleExamples of use
Die herbizide Wirkung der Phosphor-haltigen Benzoyl-Derivate der Formel I ließ sich durch die folgenden Gewächshausversuche zeigen:The herbicidal activity of the phosphorus-containing benzoyl derivatives of the formula I was demonstrated by the following greenhouse tests:
Als Kulturgefäße dienten Plastikblumentöpfe mit lehmigem Sand mit etwa 3,0 % Humus als Substrat. Die Samen der Testpflanzen wurden nach Arten getrennt eingesät.Plastic flower pots with loamy sand with about 3.0% humus as substrate served as culture vessels. The seeds of the test plants were sown separately according to species.
Bei Vorauflaufbehandlung wurden die in Wasser suspendierten oder emulgierten Wirkstoffe direkt nach Einsaat mittels fein vertei- lender Düsen aufgebracht. Die Gefäße wurden leicht beregnet, um Keimung und Wachstum zu fördern, und anschließend mit durchsichtigen Plastikhauben abgedeckt, bis die Pflanzen angewachsen waren. Diese Abdeckung bewirkt ein gleichmäßiges Keimen der Test- pflanzen, sofern dies nicht durch die Wirkstoffe beeinträchtigt wurde.In pre-emergence treatment, the active ingredients suspended or emulsified in water were applied directly after sowing using finely distributing nozzles. The tubes were lightly sprinkled to promote germination and growth, and then covered with clear plastic hoods until the plants had grown. This cover causes the test plants to germinate evenly, provided that this has not been impaired by the active ingredients.
Zum Zweck der Nachauflaufbehandlung wurden die Testpflanzen je nach Wuchsform erst bis zu einer Wuchshöhe von 3 bis 15 cm angezogen und erst dann mit den in Wasser suspendierten oder emulgier- ten Wirkstoffen behandelt. Die Testpflanzen wurden dafür entweder direkt gesät und in den gleichen Gefäßen aufgezogen oder sie wurden erst als Keimpflanzen getrennt angezogen und einige Tage vor der Behandlung in die Versuchsgefäße verpflanzt. Die Aufwandmenge für die Nachauflaufbehandlung betrug 0.5 bzw. 0.25 kg/ha a.S. (aktive Substanz) .For the purpose of post-emergence treatment, the test plants, depending on the growth habit, were first grown to a height of 3 to 15 cm and only then treated with the active ingredients suspended or emulsified in water. For this purpose, the test plants were either sown directly and grown in the same containers or they were first grown separately as seedlings and transplanted into the test containers a few days before the treatment. The application rate for post-emergence treatment was 0.5 or 0.25 kg / ha a.S. (active substance).
Die Pflanzen wurden artenspezifisch bei Temperaturen von 10 bis 25°C bzw. 20 bis 35°C gehalten. Die Versuchsperiode erstreckte sich über 2 bis 4 Wochen. Während dieser Zeit wurden die Pflanzen gepflegt, und ihre Reaktion auf die einzelnen Behandlungen wurde ausgewertet.The plants were kept in a species-specific manner at temperatures of 10 to 25 ° C and 20 to 35 ° C. The trial period lasted 2 to 4 weeks. During this time, the plants were cared for and their response to each treatment was evaluated.
Bewertet wurde nach einer Skala von 0 bis 100. Dabei bedeutet 100 kein Aufgang der Pflanzen bzw. völlige Zerstörung zumindest der oberirdischen Teile und 0 keine Schädigung oder normaler Wachstumsverlauf .Evaluation was carried out on a scale from 0 to 100. 100 means no emergence of the plants or complete destruction of at least the aerial parts and 0 means no damage or normal growth.
Die in den Gewächshausversuchen verwendeten Pflanzen setzten sich aus folgenden Arten zusammen: Bei Aufwandmengen von 0.5 bzw. 0.25 kg/ha a.S. zeigt die Verbindung 3.4 im Nachauflauf eine sehr gute Wirkung gegen die oben aufgeführten unerwünschten Pflanzen. The plants used in the greenhouse experiments are composed of the following types: At application rates of 0.5 or 0.25 kg / ha aS, compound 3.4 shows a very good effect against the undesired plants listed above.

Claims

Patentansprüche claims
1. Phosphor -haltige Benzoyl-Derivate der Formel I1. Phosphorus-containing benzoyl derivatives of the formula I.
in der die Variablen folgende Bedeutung haben:in which the variables have the following meaning:
X Sauerstoff oder Schwefel;X oxygen or sulfur;
Ri,R2 Wasserstoff, Cι-C6-Alkyl, C2 -C6 -Alkenyl, C2-C6-Alki- nyl, Hydroxy, Cι-C6 -Alkoxy, C3-C6-Alkenyloxy,R i , R 2 are hydrogen, -CC 6 alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, hydroxy, -C-C 6 alkoxy, C 3 -C6-alkenyloxy,
C3 -C6-Alkinyloxy, Mercapto, Cι-C6-Alkylthio, C3-C6 -Alkenylthio, C3-C6-Alkinylthio, Amino, Cι-C6 -Alkylamino, Di - (Cι-C6 -alkyl) amino, (Cι-C6-Alk- oxy) (Ci-Cβ-alkyl) -amino, (C3 -C6 -Alkenyl) (Ci-Cβ-al- kyDamino, (C3-C6 -Alkinyl) (Cι-C6-alkyl) amino,C 3 -C 6 alkynyloxy, mercapto, C 1 -C 6 -alkylthio, C 3 -C 6 -alkenylthio, C 3 -C 6 -alkynylthio, amino, C 1 -C 6 -alkylamino, di - (Cι-C 6 - alkyl) amino, (Cι-C 6 -alk- oxy) (Ci-Cβ-alkyl) amino, (C 3 -C 6 alkenyl) (Ci-Cβ-kyDamino al, (C 3 -C 6 alkynyl ) (-C 6 alkyl) amino,
Di (C3-C6- alkenyl) amino oder Di- (C -C6 -alkinyl) amino, wobei die genannten Alkyl-, Alkenyl - oder Alkinylreste partiell oder vollständig halogeniert sein können und/oder eine bis drei der folgenden Gruppen tragen können:Di (C 3 -C 6 -alkenyl) amino or di- (C -C 6 -alkynyl) amino, where the alkyl, alkenyl or alkynyl radicals mentioned can be partially or completely halogenated and / or carry one to three of the following groups can:
Nitro, Cyano, C1-C4 -Alkoxy, C1-C4 -Aikylthio,Nitro, cyano, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio,
C1-C4 -Alkylsulfinyl, C1-C4 -Alkylsulfonyl,C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl,
Di (Cι-C4-alkyl) -amino, C1-C4 -AIkylcarbonyl,Di (Cι-C4 alkyl) amino, C 1 -C 4 -AIkylcarbonyl,
C1-C4 -Alkoxycarbonyl, Phenyl oder Heterocyclyl, wo- bei die beiden letztgenannten Reste seinerseits partiell oder vollständig halogeniert sein können und/oder eine bis drei der folgenden Gruppen tragen können: Nitro, Cyano, Cι-C4-Alkyl, C1-C4 -Halogenalkyl, C1-C4 -Alkoxy, C1-C4 -Halogenalkoxy oder C1-C4 -Alkoxycarbonyl;C 1 -C 4 alkoxycarbonyl, phenyl or heterocyclyl, where the latter two radicals can in turn be partially or completely halogenated and / or can carry one to three of the following groups: nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy or C 1 -C 4 alkoxycarbonyl;
Phenyl oder Phenoxy, das partiell oder vollständig halogeniert sein kann und/oder eine bis drei der folgenden Gruppen tragen kann: Nitro, Cyano, C1-C4 -Alkyl, C1-C -Halogenalkyl, C1-C4 -Alkoxy, C1-C4 -Halogenalkoxy oder C1-C4-Alkoxycarbonyl ; oderPhenyl or phenoxy, which can be partially or completely halogenated and / or can carry one to three of the following groups: Nitro, cyano, C 1 -C 4 alkyl, C 1 -C haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy or C 1 -C 4 alkoxycarbonyl; or
Ri und R2 bilden gemeinsam eine -0- (CH2)m-0- , -0- (CH2)m-S- , -S- (CH2)m-S-, -NR5- (CH2)m-NR5-, -0- (CH2) m-NR5- , -S- (CH2)m-NR5-, -(CH2)n-0-, - (CH2)n-S- Oder - (CH2)n-NR5-Kette aus, die einen bis drei Reste aus folgender Gruppe tragen kann:R i and R 2 together form a -0- (CH 2 ) m -0-, -0- (CH 2 ) m -S-, -S- (CH 2 ) m -S-, -NR 5 - (CH 2 ) m -NR 5 -, -0- (CH 2 ) m -NR 5 -, -S- (CH 2 ) m -NR 5 -, - (CH 2 ) n -0-, - (CH 2 ) n -S- Or - (CH 2 ) n -NR 5 chain, which can carry one to three residues from the following group:
Halogen, Cyano, C1-C4 -Alkyl, C1-C4 -Halogenalkyl, C1-C4 -Alkoxy, C1-C4-Alkoxycarbonyl oder Phenyl, das unsubstituiert ist oder partiell oder vollständig halogeniert ist und/oder eine bis drei der folgen- den Gruppen tragen kann:Halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkoxycarbonyl or phenyl, which is unsubstituted or partially or completely halogenated and / or can carry one to three of the following groups:
Nitro, Cyano, Cι-C4-Alkyl, C3.-C4-Halogenalkyl, C1-C4 -Alkoxy, C1-C4- Halogenalkoxy oder C1-C4 -Alkoxycarbonyl ;Nitro, cyano, C 4 alkyl, C 3 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 - haloalkoxy or C 1 -C 4 alkoxycarbonyl;
oderor
R und R2 bilden gemeinsam eine - (CH2)p-Kette, die durch Sauerstoff, Schwefel oder NR5 unterbrochen sein kann und/oder einen bis drei Reste aus folgender Gruppe tragen kann:R and R 2 together form a - (CH 2 ) p chain, which can be interrupted by oxygen, sulfur or NR 5 and / or can carry one to three radicals from the following group:
Halogen, Cyano, Cι-C4-Alkyl, C1-C4- Halogenalkyl, C1-C4 -Alkoxy, C1-C4 -Alkoxycarbonyl oder Phenyl, das unsubstituiert ist oder partiell oder vollständig halogeniert ist und/oder eine bis drei der folgen- den Gruppen tragen kann:Halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkoxycarbonyl or phenyl, which is unsubstituted or partially or completely halogenated and / or one can carry up to three of the following groups:
Nitro, Cyano, Cι-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4 -Alkoxy, C1-C4- Halogenalkoxy oder C1-C4 -Alkoxycarbonyl ;Nitro, cyano, C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 - haloalkoxy or C 1 -C 4 alkoxycarbonyl;
R3 Wasserstoff, Nitro, Cyano, Halogen, Cι-C6 -Alkyl,R 3 is hydrogen, nitro, cyano, halogen, -CC 6 alkyl,
Ci -C6 -Halogenalkyl , Ci -C6 -Alkoxy- Ci - C6 - alkyl , Ci -C6 -Halogenalkoxy- Ci -C6 -alkyl , Ci - C6 -Alkyl - thio -Ci -C6 - alkyl , Ci - C6 -Alkylsulfinyl -Ci - C6 - alkyl , Ci -C6 -Alkylsulfonyl -Ci -C6 - alkyl , Ci -C6 -Alkylcarbo- nyl, Cι-C6 -Alkoxycarbonyl, Cι-C6 -Alkoxy, Ci-Cβ-Halo- genalkoxy, Ci-Cß-Alkylthio, Cι-C6 -Halogenalkylthio, Ci -C6 -Alkylsulfinyl , Ci -Cβ -Halogenalkylsulf inyl , Ci -Cδ -Alkylsulfonyl , Ci -C6 - Halogenalkylsulfonyl , Aminosulfonyl, Cι-C6 -Alkylaminosulfonyl, Di- (Cι-C6- alkyl) aminosulfonyl, (Cι-C6-Alkylsulfo- nyl) amino, (Ci-Cg-Halogenalkylsulfonyl) amino, N- (Ci-Cβ-Alkyl) -N- (Cι-C6-alkylsulfonyl) amino, N- (Ci-Cδ-Alkyl) -N- (Ci -C6-halogenalkylsulfo- nyl) amino, -P(=X)RiR2, Phenyl oder Heterocyclyl, wobei die beiden letztgenannten Reste partiell oder vollständig halogeniert sein können und/oder einen bis drei der folgenden Gruppen tragen können:Ci -C 6 haloalkyl, Ci -C 6 alkoxy- Ci - C 6 alkyl, Ci -C 6 haloalkoxy- Ci -C 6 alkyl, Ci - C 6 alkyl - thio -Ci -C 6 alkyl , Ci - C 6 alkylsulfinyl -Ci - C 6 - alkyl, Ci -C 6 alkylsulfonyl -Ci -C 6 - alkyl, Ci -C 6 alkylcarbonyl, Cι-C 6 -alkoxycarbonyl, Cι-C 6 - Alkoxy, Ci-Cβ-haloalkoxy, Ci-Cß-alkylthio, Cι-C 6 -haloalkylthio, Ci -C 6 alkylsulfinyl, Ci -Cβ -haloalkylsulfonyl, Ci -Cδ -alkylsulfonyl, Ci -C 6 - haloalkylsulfonyl, aminosulfonyl, Cι-C 6 alkylaminosulfonyl, di- (Cι-C 6 - alkyl) aminosulfonyl, (Cι-C 6 -Alkylsulfo- nyl) amino, (Ci-Cg haloalkylsulfonyl) amino, N- (Ci-Cβ-alkyl ) -N- (-CC 6 alkylsulfonyl) amino, N- (Ci-C δ- alkyl) -N- (Ci-C 6 -haloalkylsulfonyl) amino, -P (= X) R i R 2 , phenyl or heterocyclyl, the latter two radicals being partially or completely halogenated can and / or can carry one to three of the following groups:
Nitro, Cyano, Cι-C4-Alkyl, Ci -C4 -Halogenalkyl, C1-C4 -Alkoxy, C1-C4 -Halogenalkoxy oder C1-C4 -Alkoxycarbonyl;Nitro, cyano, C 4 alkyl, Ci -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 -haloalkoxy or C 1 -C 4 alkoxycarbonyl;
R4 Nitro, Cyano, Halogen, Cι-C6 -Alkyl, Cι-C6 -Alkoxy,R 4 nitro, cyano, halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy,
Cι-C6 -Aikylthio, Cι-C6 -Alkylsulfinyl oder Cι-C6-Al- kylsulfonyl;C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl or C 1 -C 6 alkyl sulfonyl;
R5 Wasserstoff, Cι-C6-Alkyl, Cι-C6-Halogenalkyl oderR 5 are hydrogen, C 6 -alkyl, C 6 haloalkyl or
Cι-C6 -Alkoxy;-C 6 alkoxy;
1 0 , 1 oder 2 ;1 0, 1 or 2;
m 2,3 oder 4;m 2, 3 or 4;
n 3.4 oder 5 ;n 3.4 or 5;
P 4.5 oder 6 ;P 4.5 or 6;
ein Rest der Formel Q1, Q2, Q3 oder Q4 a radical of the formula Q 1 , Q 2 , Q 3 or Q 4
Q Q2 Q3 Q4 QQ 2 Q 3 Q 4
R6 Hydroxy, Mercapto , Halogen, ORi3 , SR13 , SORi4 , S02Rl4 , OS02Ri4 , PORl5Rl6 , OPRl 5R 6 , OPOR15R16 ,R 6 is hydroxy, mercapto, halogen, OR i3, SR 13, SOR i4, S0 2 R l4, OS0 2 R i4, POR l5 R l6, OPR l 5 R 6, OPOR 15 R 16,
OPSR 5R16 , NR17Ri8 , ONRi8Ri9 , N- gebundenes Hetero cyclyl oder 0- (N-gebundenes Heterocyclyl ) , wobei der Heterocyclyl - Rest der beiden letztgenannten Substituenten partiell oder vollständig haloge- niert sein kann und/oder einen bis drei der fol genden Reste tragen kann : Nitro, Cyano, C1-C4 -Alkyl, C1-C4-Halogenalkyl, C1-C4 -Alkoxy oder Ci -C4 -Halogenalkoxy;OPSR 5 R 16 , NR 17 R i8 , ONR i8 R i9 , N-linked heterocyclic or 0- (N-linked heterocyclyl), where the heterocyclyl radical of the latter two substituents can be partially or completely halogenated and / or can carry one to three of the following residues: Nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or Ci -C 4 haloalkoxy;
R ,R9,Riι Wasserstoff, Nitro, Halogen, Cyano, Cι-C6-Alkyl, Ci-Cδ-Halogenalkyl, Di- (Cι-C6- alkoxy) -methyl,R, R 9 , R i ι hydrogen, nitro, halogen, cyano, Cι-C 6 alkyl, Ci-C δ -haloalkyl, di- (Cι-C 6 - alkoxy) methyl,
Di- (Cι-C6-alkylthio) -methyl, (Cι-C6 -Alkoxy) (Cι-C6- alkylthio) -methyl, Hydroxy, Cι-C6-Alkoxy, Cχ-C6-Halogenalkoxy, Ci -C6 -Alkoxycarbonyloxy, Cι-C6-Alkylthio, Cι-C6-Halogenalkylthio, Ci-Cδ-Alkylsulfinyl, Ci-Cβ-Halogenalkylsulfinyl ,Di- (Cι-C 6 -alkylthio) methyl, (Cι-C6 alkoxy) (Cι-C 6 - alkylthio) methyl, hydroxy, Cι-C 6 -alkoxy, Cχ-C 6 haloalkoxy, Ci - C 6 -alkoxycarbonyloxy, -C-C 6 -alkylthio, Cι-C 6 -haloalkylthio, Ci-Cδ-alkylsulfinyl, Ci-Cβ-haloalkylsulfinyl,
Ci-Cβ-Alkylsulfonyl , Cι-C6-Halogenalkylsulfonyl , Ci-Cδ-Alkylcarbonyl , Ci-Cβ-Halogenalkylcarbonyl , Ci-Cδ-Alkoxycarbonyl oder Ci-Cö-Halogenalkoxycarbo- nyl;Ci-Cβ-alkylsulfonyl, Cι-C 6 haloalkylsulfonyl, Ci-C δ- alkylcarbonyl, Ci-Cβ-haloalkylcarbonyl, Ci-Cδ-alkoxycarbonyl or Ci-Cö-haloalkoxycarbonyl;
R8,Ri°,Ri2 Wasserstoff, Cι-C6-Alkyl, Cι-C6 -Alkoxy, Cι-C6-Al- kyl hio oder Ci -C6-Alkoxycarbonyl ;R 8, R i o, R i2 are hydrogen, C 6 -alkyl, C 6 -alkoxy, C 6 -Al- hio alkyl or Ci-C6 alkoxycarbonyl;
oderor
R7 und R8 oder R9 und R10 oder Ru und Ri2 bilden gemeinsam eine -0- (CH2)u-0- , -0- (CH2)U-S- , -S- (CH2)U-S- , -0- (CH2)V- oder -S- (CH ) V-Kette, die durch einen bis drei Reste aus folgender Gruppe substituiert sein kann:R 7 and R 8 or R 9 and R 10 or R u and R i2 together form a -0- (CH 2 ) u -0-, -0- (CH 2 ) U -S-, -S- (CH 2 ) U -S-, -0- (CH 2 ) V - or -S- (CH) V chain, which can be substituted by one to three radicals from the following group:
Halogen, Cyano, C1-C4 -Alkyl, C1-C4-Halogenalkyl oder C1-C4 -Alkoxycarbonyl;Halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 alkoxycarbonyl;
oderor
R7 und R8 oder R9 und R10 oder R11 und R12 bilden gemeinsam eine - (CH )W-Kette, die durch Sauerstoff oder Schwefel unterbrochen sein kann und/oder durch einen bis vier Reste aus folgender Gruppe substi- tuiert sein kann:R 7 and R 8 or R 9 and R 10 or R 11 and R 12 together form a - (CH) W chain, which can be interrupted by oxygen or sulfur and / or substituted by one to four radicals from the following group can be:
Halogen, Cyano, C1-C4 -Alkyl, C1-C4 -Halogenalkyl oder C1-C4 -Alkoxycarbonyl ;Halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 alkoxycarbonyl;
oderor
R7 und R8 oder R9 und R10 oder R11 und R12 bilden gemeinsam eine Methylidengruppe, die durch einen bis zwei Reste aus folgender Gruppe substituiert sein kann: Halogen, Hydroxy, Formyl, Cyano, Cι-C6-Alkyl, Ci-Cδ-Halogenalkyl, Cι-C6-Alkoxy, Ci-Cö-Halogen- alkoxy, Cι-C6-Alkylthio, Cι-C6-Halogenalkylthio, Cι-C6-Alkylsulfinyl, Cι-C6-Halogenalkylsulf inyl, Ci-Cβ-Alkylsulfonyl oder Ci-Cö-Halogenalkyl- sulfonyl;R 7 and R 8 or R 9 and R 10 or R 11 and R 12 together form a methylidene group which can be substituted by one or two radicals from the following group: halogen, hydroxy, formyl, cyano, C 1 -C 6 alkyl, Ci-C δ haloalkyl, Cι-C6 alkoxy, Ci-COE-halo- alkoxy, Cι-C 6 alkylthio, Cι-C 6 haloalkylthio, Cι-C 6 alkylsulfinyl, Cι-C 6 ynyl -Halogenalkylsulf , Ci-Cβ-alkylsulfonyl or Ci-C ö -haloalkyl-sulfonyl;
oderor
R7 und R8 oder R9 und R10 oder R11 und Ri2 bilden gemeinsam mit dem Kohlenstoff an den sie gebunden sind eine Carbonylgruppe aus;R 7 and R 8 or R 9 and R 10 or R 11 and R i2 together with the carbon to which they are attached form a carbonyl group;
oderor
R7 und R9 oder R9 und R11 oder R7 und R11 bilden gemeinsam eine - (CH2) V-Kette, die durch einen bis drei Reste aus folgender Gruppe substituiert sein kann: Halogen, Cχ-C6 -Alkyl, Cι-C6 -Alkoxy, Hydroxy oderR 7 and R 9 or R 9 and R 11 or R 7 and R 11 together form a - (CH 2 ) V chain, which can be substituted by one to three radicals from the following group: halogen, Cχ-C 6 alkyl , -CC 6 alkoxy, hydroxy or
Ci -C6 -Alkoxycarbonyl ,-Ci -C 6 alkoxycarbonyl, -
Ri3 Cι-C6-Alkyl, C3-C6-Alkenyl , C3-C6-Halogenalkenyl, C3-C6-Alkinyl, C3-C6-Halogenalkinyl, C3-C6-Cyclo- alkyl, Cι-C2n.-Alkylcarbonyl, C2-C6-Alkenylcarbonyl,R i3 -CC 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl, C 3 -C 6 cycloalkyl , -C 2 -N.-alkylcarbonyl, C 2 -C 6 alkenylcarbonyl,
C2-C6-Alkinylcarbonyl , C3-C6-Cycloalkylcarbonyl , Ci -Cβ -Alkylaminocarbonyl , Ci-Cö-Alkylcarbo- nyl-Cι-C6-alkyl oder Cι-C6-Alkoxyimino-Cι-C6-alkyl, wobei die genannten Alkyl- und Cycloalkylreste partiell oder vollständig halogeniert sein können und/oder eine bis drei der folgenden Gruppen tragen können:C 2 -C 6 -alkynylcarbonyl, C 3 -C 6 -cycloalkylcarbonyl, Ci -Cβ -alkylaminocarbonyl, Ci-C ö -alkylcarbonyl-Cι-C 6 -alkyl or Cι-C 6 -alkoxyimino-Cι-C 6 - alkyl, where the alkyl and cycloalkyl radicals mentioned can be partially or completely halogenated and / or can carry one to three of the following groups:
Cyano, Cι-C4-Alkoxy, Cι-C4-Alkylthio, Di- (C1-C4- alkyl) -amino, Cι-C4-Alkylcarbonyl, C1-C4-Alkoxy- carbonyl, Cι-C4-Alkoxy-Cι-C4-alkoxycarbonyl,Cyano, C 4 -alkoxy, C 4 alkylthio, di (C 1 -C 4 - alkyl) amino, Cι-C4-alkylcarbonyl, C1-C4 alkoxy carbonyl, Cι-C 4 - Alkoxy-C 4 -alkoxycarbonyl,
Di- (Cι~C4-alkyl) -amino-Cι-C4-alkoxycarbonyl , Hydroxycarbonyl , C1-C4-Alkylaminocarbonyl, Di- (Cι-C-alkyl) -aminocarbonyl, Aminocarbonyl, Cι-C4-Alkylcarbonyloxy oder C3-C6-Cycloalkyl;Di- (-C ~ C 4 -alkyl) amino -CC-C 4 -alkoxycarbonyl, hydroxycarbonyl, C 1 -C 4 -alkylaminocarbonyl, di- (-C-C-alkyl) -aminocarbonyl, aminocarbonyl, Cι-C 4 -alkylcarbonyloxy or C 3 -C 6 cycloalkyl;
Phenyl, Heterocyclyl, Phenyl-Ci-Cβ-alkyl, Heterocy- clyl-Ci-Cö-alkyl, Phenylcarbonyl, Heterocyclylcar- bonyl, Phenylaminocarbonyl oder Heterocyclylamino- carbonyl, wobei der Phenyl- und der Heterocyclyl- Rest der 8 letztgenannten Substituenten partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann: Nitro, Cyano, Cι-C4-Alkyl, Cι-C4-Halogenalkyl, Cι-C4~Alkoxy oder Cι-C4-Halogenalkoxy,-Phenyl, heterocyclyl, phenyl-Ci-Cβ-alkyl, heterocyclyl-Ci-C ö alkyl, phenylcarbonyl, Heterocyclylcar- carbonyl, phenylaminocarbonyl or heterocyclylamino carbonyl, wherein the phenyl and the heterocyclyl radical of the 8 last-mentioned substituents partially or Cι-C nitro, cyano, C 4 alkyl, 4-haloalkyl, Cι-C4 ~ alkoxy or Cι-C4-haloalkoxy, -: can be completely halogenated and / or may carry one to three of the following radicals
Ri4 , Ri5 , Ri6 Cι-C6-Alkyl , C3-C6-Alkenyl , C3-C6-Halogenalkenyl , C3-C6~Alkinyl, C3-C6-Halogenalkinyl, C3-C6-Cyclo- alkyl, Hydroxy, Cι-C6-Alkoxy, Amino, Ci-Cβ-Alkyl- amino, Cx-Cg-Halogenalkylamino, Di-(Cι-C6- alkyDamino oder Di- (Cι-C6-halogenalkyl) amino, wobei die genannten Alkyl-, Cycloalkyl- und Alkoxyreste partiell oder vollständig halogeniert sein können und/oder eine bis drei der folgenden Gruppen tragen können:R i4 , R i5 , R i6 -CC 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 ~ alkynyl, C 3 -C 6 haloalkynyl, C 3 - C 6 cyclo alkyl, hydroxy, -C 6 -alkoxy, amino, Ci-Cβ-alkylamino, Cx-Cg-haloalkylamino, di- (-C-C 6 - alkyDamino or di- (-C-C 6 -haloalkyl) amino, where the alkyl, cycloalkyl and alkoxy radicals mentioned can be partially or completely halogenated and / or can carry one to three of the following groups:
Cyano, Cι-C4-Alkoxy, Cι-C -Alkylthio, Di- (C1-C4- alkyl) -amino, Cι-C4~Alkylcarbonyl oder Cι-C4-Alkoxycarbonyl;Cyano, C 4 -alkoxy, C alkylthio, di- (C 1 -C 4 - alkyl) amino, Cι-C ~ 4 alkylcarbonyl or Cι-C 4 alkoxycarbonyl;
Phenyl, Heterocyclyl, Phenoxy oder Heterocyclyloxy, wobei der Phenyl- und der Heterocyclyl- Rest der letztgenannten Substituenten partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann: Nitro, Cyano, Cι-C4-Alkyl, Cι-C4-Halogenalkyl, Cι-C4~Alkoxy oder C1-C4-Halogenalkoxy;Phenyl, heterocyclyl, phenoxy or heterocyclyloxy, where the phenyl and heterocyclyl radicals of the latter substituents can be partially or completely halogenated and / or can carry one to three of the following radicals: nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, Cι-C 4 -alkoxy or C 1 -C 4 -haloalkoxy;
Ri"7 Ci-Ce -Alkyl, C3-C6 -Alkenyl, C -C6-Halogenalkenyl,R i "7 Ci-Ce alkyl, C 3 -C 6 alkenyl, C -C 6 haloalkenyl,
C3-C6 -Alkinyl, C3-C6 -Halogenalkinyl, C3-C6-Cyclo- alkyl, Hydroxy, Cι-C6 -Alkoxy, C3-C6-Alkenyloxy oder C3 -Cβ-Alkinyloxy, wobei die genannten Alkyl-, Cycloalkyl- und Alkoxyreste partiell oder voll- ständig halogeniert sein können und/oder einen bis drei Reste der folgenden Gruppe tragen können: Cyano, C1-C4 -Alkoxy, C1-C4 -Aikylthio oder Di- (Cι~C4-alkyl) -amino;C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl, C 3 -C 6 -cycloalkyl, hydroxy, Cι-C 6 -alkoxy, C 3 -C 6 alkenyloxy or C 3 -Cβ-alkynyloxy, where the alkyl, cycloalkyl and alkoxy radicals mentioned can be partially or completely halogenated and / or can carry one to three radicals from the following group: cyano, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio or di - (-C ~ C 4 alkyl) amino;
Phenyl, Heterocyclyl, Phenyl -Cι-C6-alkyl oder Hete- rocyclyl-Ci-Cβ -alkyl, wobei der Phenyl- oder Heterocyclyl-Rest der vier letztgenannten Substituenten partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann:Phenyl, heterocyclyl, phenyl -C-C 6 alkyl or heterocyclyl-Ci-Cβ-alkyl, where the phenyl or heterocyclyl radical of the four last-mentioned substituents can be partially or completely halogenated and / or one to three of the following radicals can carry:
Nitro, Cyano, C1-C4 -Alkyl, C1-C4 -Halogenalkyl, C1-C4 -Alkoxy oder C1-C4 -Halogenalkoxy;Nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy;
R8, Ri9 Cι-C6 -Alkyl, C3-C6 -Alkenyl, C3-C6-Alkinyl oder Cι-C6-Alkylcarbonyl;R 8 , R i9 -CC 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl or C 6 -C 6 alkylcarbonyl;
u 2 bis 4;u 2 to 4;
v 1 bis 5;v 1 to 5;
w 2 bis 5; R20 ein Rest wie unter R6 genannt;w 2 to 5; R 20 is a radical as mentioned under R 6 ;
R21 Wasserstoff, Cι-C6 -Alkyl, Cι-C6 -Halogenalkyl, Hydroxy, Cι-C6 -Alkoxy oder Ci-Cß -Halogenalkoxy; R 21 are hydrogen, C 6 -alkyl, C 6 haloalkyl, hydroxy, Cι-C 6 alkoxy or Ci-C -haloalkoxy ß;
R22 Wasserstoff, Halogen, Cχ-C6-Alkyl, Ci-Cδ-Halogenal kyl, Hydroxy, CI-CÖ -Alkoxy, Cι-C6 -Halogenalkoxy, Cι-C6 -Aikylthio oder Cχ-C6 -Halogenalkylthio; R 22 is hydrogen, halogen, Cχ-C 6 -alkyl, Ci-C δ -halogenal kyl, hydroxy, C I -C Ö -alkoxy, Cι-C 6 -haloalkoxy, Cι-C 6 -alkylthio or Cχ-C 6 - Haloalkylthio;
R23 Wasserstof f , Ci -Cβ -Alkyl , Cι - C6 -Halogenalkyl , C3 -C6 - Cycloalkyl oder C3 -C6 -Halogencycloalkyl ; R 23 hydrogen f, Ci -Cβ alkyl, Cι - C 6 haloalkyl, C 3 -C 6 cycloalkyl or C 3 -C 6 halocycloalkyl;
R2 Wasserstoff, Cι-C6 -Alkoxycarbonyl, Ci-Cö-Halo- genalkoxycarbonyl, Hydroxycarbonyl oder Cyano; R 2 are hydrogen, C 6 alkoxycarbonyl, Ci-C ö -Halo- genalkoxycarbonyl, hydroxycarbonyl or cyano;
R25 Cι-C6-Alkyl, Cι-C6 -Halogenalkyl, C3 -C6 -Cycloalkyl oder C3-C6-Halogencycloalkyl; R 25 Cι-C 6 -alkyl, C 6 haloalkyl, C 3 -C 6 -cycloalkyl or C 3 -C 6 halocycloalkyl;
sowie deren landwirtschaftlich brauchbaren Salze.and their agriculturally useful salts.
Phosphor -haltige Benzoyl-Derivate der Formel I gemäß Anspruch 1, wobei Q für Qi steht (la)Phosphorus-containing benzoyl derivatives of the formula I according to claim 1, where Q is Q i (la)
Phosphor -haltige Benzoyl-Derivate der Formel I gemäß Anspruch 1, wobei Q für Q2 steht (Ib)Phosphorus-containing benzoyl derivatives of the formula I according to claim 1, where Q is Q 2 (Ib)
Phosphor-haltige Benzoyl-Derivate der Formel I gemäß den Ansprüchen 1 bis 3, wobei X=0 bedeutet und R3 in 4 -Position, R4ι in 5-Position und "P(=X)R!R2" in 2-Position gebunden sind (II) . Phosphorus-containing benzoyl derivatives of the formula I according to claims 1 to 3, where X = 0 and R 3 in the 4 position, R 4 in the 5 position and "P (= X) R ! R 2 " in 2 -Position are bound (II).
Phosphor -haltige Benzoyl-Derivate der Formel I gemäß den An- Sprüchen 1 bis 3, wobei X=0 bedeutet und R3 in 2 -Position, R4ι in 5 -Position und "P(=X)R1R2" in 4 -Position gebunden sind (12) .Phosphorus-containing benzoyl derivatives of the formula I according to claims 1 to 3, where X = 0 and R 3 in the 2 position, R 4 in the 5 position and "P (= X) R 1 R 2 " are bound in the 4 position (12).
Phosphor -haltige Benzoyl-Derivate der Formel I gemäß den Ansprüchen 1 bis 5, wobei die VariablenPhosphorus-containing benzoyl derivatives of the formula I according to claims 1 to 5, wherein the variables
Rl,R2 Wasserstoff, Ci-Cö-Alkyl, Hydroxy, Cι-C6-Alkoxy, Ci-Cδ-Alkylthio, Di - (Cι-C6 -alkyl) amino, wobei die Alkylreste der fünf letztgenannten Substituienten partiell oder vollständig halogeniert sein können und/oder eine bis drei der folgenden Gruppen tragen können:R l , R 2 is hydrogen, Ci-C ö alkyl, hydroxy, -C-C 6 alkoxy, Ci-C δ -alkylthio, di - (Cι-C 6 alkyl) amino, the alkyl radicals of the five latter substituents being partial or can be completely halogenated and / or can carry one to three of the following groups:
Nitro, Cyano, C1-C4 -Alkoxy, Cχ-C4 -Alkylsulfonyl oder C1-C4 -Alkoxycarbonyl ; bedeuten oderNitro, cyano, C 1 -C 4 alkoxy, Cχ-C 4 alkylsulfonyl or C 1 -C 4 alkoxycarbonyl; mean or
R1 und R2 bilden gemeinsam eine -0- (CH )m-0- , -O- (CH2)m-S- , -S- (CH2)m-S-, -NR5- (CH2)m-NR5-, -0- (CH2)m-NR5 - , -S- (CH2)m-NR5- oder - (CH2)P-Kette aus, die einen bis drei Reste aus folgender Gruppe tragen kann: Halogen, Cyano, C1-C4 -Alkyl oder Cι-C4-Alkoxycar- bony.R 1 and R 2 together form a -0- (CH) m -0-, -O- (CH 2 ) m -S-, -S- (CH 2 ) m -S-, -NR 5 - (CH 2 ) m -NR 5 -, -0- (CH 2 ) m -NR 5 -, -S- (CH 2 ) m -NR 5 - or - (CH 2 ) P chain, which contain one to three residues from the following Group can carry: Halogen, cyano, C 1 -C 4 alkyl or C 1 -C 4 alkoxycar- bony.
Phosphorhaltige Benzoyl-Derivate der Formel I gemäß den Ansprüchen 1 bis 6, wobeiPhosphorus-containing benzoyl derivatives of the formula I according to claims 1 to 6, wherein
R3 Nitro, Halogen, Cι-C4-Alkyl, Ci -C4 -Halogenalkyl ,R 3 nitro, halogen, -CC 4 alkyl, Ci -C 4 haloalkyl,
Cι-C4-Alkoxy, C1-C4 -Halogenalkoxy, Cι-C4-Alkylthio, C1-C4 -Alkylsulfonyl, C1-C4 -Halogenalkylsulf onyl, -P(=0) (CH3)2, -P(=0) (CH2CH3)2, -P(=0) (OCH3)2 oder -P(=0) (OCH2CH3)2;Cι-C 4 alkoxy, C 1 -C 4 haloalkoxy, Cι-C 4 alkylthio, C 1 -C 4 alkylsulfonyl, C 1 -C 4 -Halogenalkylsulf onyl, -P (= 0) (CH 3) 2 , -P (= 0) (CH 2 CH 3 ) 2 , -P (= 0) (OCH 3 ) 2 or -P (= 0) (OCH 2 CH 3 ) 2 ;
bedeutet.means.
Verfahren zur Herstellung von Verbindungen der Formel la (= I mit Q=Qi) mit R6 = Halogen oder von Verbindungen der Formel Ib ( ≡ I mit Q=Q2) mit R20 = Halogen gemäß Anspruch 1, dadurch gekennzeichnet, daß manA process for the preparation of compounds of the formula Ia (= I with Q = Q i ) with R 6 = halogen or of compounds of the formula Ib (≡ I with Q = Q 2 ) with R 20 = halogen according to Claim 1, characterized in that one
a) ein entsprechendes Phosphor-haltiges Benzoylderivat der Formel la ( ≡ I mit Q=Qi) mit R6 = Hydroxya) a corresponding phosphorus-containing benzoyl derivative of the formula la (≡ I with Q = Q i ) with R 6 = hydroxy
oderor
b) ein entsprechendes Phosphor-haltiges Benzoylderivat der Formel Ib (≡ I mit Q=Q2) mit R20 = Hydroxyb) a corresponding phosphorus-containing benzoyl derivative of the formula Ib (≡ I with Q = Q 2 ) with R 20 = hydroxy
wobei die Variablen X, R1 bis R4, R7 bis Ri2, R21 bis R22 und 1 die in Anspruch 1 genannte Bedeutung haben, mit einem Haloge- nierungsmittel umsetzt. where the variables X, R 1 to R 4 , R 7 to R i2 , R 21 to R 22 and 1 have the meaning given in claim 1, are reacted with a halogenating agent.
Verfahren zur Herstellung von Verbindungen der Formel la (≡ I mit Q=Q!) mit R6 = OR13, OS02Rl4, OPR15Rl6, OPORl5Rl6 oder OPSR15Rl6 oder von Verbindungen der Formel Ib ( ≡ I mit Q=Q2) mit R20 = ORi3, OS02R14, OPRi5Ri6, OPORi5Ri6 oder OPSRi5Ri6 gemäß Anspruch 1, dadurch gekennzeichnet, daß manA process for the preparation of compounds of formula la (≡ I where Q = Q!) Where R 6 = OR 13, OS0 2 R l4, OPR 15 R l6, OPOR l5 R l6 or OPSR 15 R l6 or of compounds of formula Ib ( ≡ I with Q = Q 2 ) with R 20 = OR i3 , OS0 2 R 14 , OPR i5 R i6 , OPOR i5 R i6 or OPSR i5 R i6 according to claim 1, characterized in that
a) ein entsprechendes Phosphor- haltiges Benzoylderivat der Formel la (≡ I mit Q=Q!) mit R6 = Hydroxya) a corresponding phosphorus-containing benzoyl derivative of the formula la (≡ I with Q = Q ! ) with R 6 = hydroxy
oderor
b) ein entsprechendes Phosphor-haltiges Benzoylderivat der Formel Ib (≡ I mit Q=Q2) mit R20 = Hydroxyb) a corresponding phosphorus-containing benzoyl derivative of the formula Ib (≡ I with Q = Q 2 ) with R 20 = hydroxy
wobei die Variablen X, R bis R4, R7 bis R12, R2i bis R22 und 1 die in Anspruch 1 genannte Bedeutung haben, mit einer Verbindung der Formel Ilα, Ilß, Ilγ, ilδ oder Ilε,where the variables X, R to R 4 , R 7 to R 12 , R 2i to R 22 and 1 have the meaning given in claim 1, with a compound of the formula Ilα, Ilß, Ilγ, ilδ or Ilε,
L1 - R13 Ll - S02R14 Li - PRlSR16 LlPORi 5R16 L! - PSR15Rl6 L 1 - R13 Ll - S0 2 R 14 Li - PRl S R 16 L l POR i 5 R 16 L! - PSR 15 Rl 6
( ilα) (ilß) ( ilγ) ( ilδ) ( ilε) wobei die Variablen Ri3 bis Ri6 die in Anspruch 1 genannte Bedeutung haben und L1 für eine nucleophil verdrängbare Abgangsgruppe steht, umsetzt.(ilα) (ilß) (ilγ) (ilδ) (ilε) where the variables R i3 to R i6 have the meaning given in claim 1 and L 1 stands for a nucleophilically displaceable leaving group.
Verfahren zur Herstellung von Verbindungen der Formel laProcess for the preparation of compounds of formula la
(≡ I mit Q=Ql) mit R = ORi3, SRi3, PORl5Rl6, NRl7Rl8, ONRl8R19, N-gebundenes Heterocyclyl oder O-N-gebundenes Heterocyclyl oder von Verbindungen der Formel Ib ( ≡ I mit Q=Q2) mit R20 = 0RI3, SRi3, PORX5Ri6, NRi7Ri8, ONRi8Ri9, N-gebundenes Hete- rocyclyl gemäß Anspruch 1, dadurch gekennzeichnet, daß man(≡ I where Q = Q l) with R = OR i3, SR i3, POR l5 R l6, NR l7 R l8, ONR l8 R 19, N-bonded heterocyclyl or ON-bonded heterocyclyl or of compounds of formula Ib (≡ I with Q = Q 2 ) with R 20 = 0R I3 , SR i3 , POR X5 R i6 , NR i7 R i8 , ONR i8 R i9 , N-linked heterocyclyl according to claim 1, characterized in that
a) ein entsprechendes Phosphor-haltiges Benzoylderivat der Formel la ( ≡ I mit Q=Q!) mit R6 = Halogen oder OS02Ri4 a) a corresponding phosphorus-containing benzoyl derivative of the formula la (≡ I with Q = Q ! ) with R 6 = halogen or OS0 2 Ri 4
la mit R6 = Halogen oder OS02Ri4 la with R 6 = halogen or OS0 2 R i4
oderor
b) ein entsprechendes Phosphor-haltiges Benzoylderivat der Formel Ib ( ≡ I mit Q=Q2) mit R20 = Halogen oder OS0Ri4 b) a corresponding phosphorus-containing benzoyl derivative of the formula Ib (≡ I with Q = Q 2 ) with R 20 = halogen or OS0Ri 4
Ib mi t R20 = Halogen oder OS02Ri4 Ib with R 20 = halogen or OS0 2 R i4
wobei die Variablen X, Ri bis R4, R7 bis R2, R14 , R21 bis R22 und 1 die in Anspruch 1 genannte Bedeutung haben, mit einer Verbindung der Formel Illα, HIß, Illγ, Illδ oder Illε, Illη oder Illθwhere the variables X, R i to R 4 , R 7 to R 2 , R 14 , R 21 to R 22 and 1 have the meaning given in claim 1, with a compound of the formula Illα, HIß, Illγ, Illδ or Illε, Illη or Illθ
HORl3 HSRi3 HPOR15Rl6 HNR Rl8 HONRlδR9 (Illα) (HIß) (iiiγ) (IHδ) (ilε) H (N-gebundenes Heterocyclyl) H (ON-gebundenes Heterocyclyl) (Illη) (III*)HOR l3 HSR i3 HPOR 15 R l6 HNR Rl 8 HONR lδ R 9 (Illα) (HIß) (iiiγ) (IHδ) (ilε) H (N-bound heterocyclyl) H (ON-bound heterocyclyl) (Illη) (III *)
wobei die Variablen R13 bis Ri9 die in Anspruch 1 genannte Be- deutung haben, gegebenenfalls in Gegenwart einer Base, umsetzt.where the variables R 13 to R i9 have the meaning given in claim 1, optionally in the presence of a base.
Verfahren zur Herstellung von Verbindungen der Formel laProcess for the preparation of compounds of formula la
(≡ I mit Q=Q ) mit R6 = SORi4, S02R14 oder von Verbindungen der Formel Ib ( ≡ I mit Q=Q2) mit R20 = SORi4, S02Ri4 gemäß Anspruch 1, dadurch gekennzeichnet, daß man(≡ I with Q = Q) with R 6 = SOR i4 , S0 2 R 14 or of compounds of the formula Ib (≡ I with Q = Q 2 ) with R 20 = SOR i4 , S0 2 R i4 according to claim 1, thereby characterized that one
a) ein entsprechendes Phosphor-haltiges Benzoylderivat der Formel la ( ≡ I mit Q=Qi) mit R6 = SRi4 a) a corresponding phosphorus-containing benzoyl derivative of the formula la (≡ I with Q = Q i ) with R 6 = SR i4
oderor
b) ein entsprechendes Phosphor-haltiges Benzoylderivat der Formel Ib ( ≡ I mit Q=Q2) mit R20 = SRi4 b) a corresponding phosphorus-containing benzoyl derivative of the formula Ib (≡ I with Q = Q 2 ) with R 20 = SR i4
wobei die Variablen X, Ri bis R4, R7 bis Ri2, Ri4, R2i bis R22 und 1 die in Anspruch 1 genannte Bedeutung haben, mit einem Oxidationsmittel umsetzt. Verfahren zur Herstellung von Verbindungen der Formel la (≡ I mit Q=Q!) mit R6 = Hydroxy oder von Verbindungen der Formel Ib ( ≡ I mit Q=Q2) mit R20 = Hydroxy, gemäß Anspruch 1, dadurch gekennzeichnet, daß manwherein the variables X, R i to R 4 , R 7 to R i2 , R i4 , R 2 i to R 22 and 1 have the meaning given in claim 1, with an oxidizing agent. Process for the preparation of compounds of the formula Ia (≡ I with Q = Q ! ) With R 6 = hydroxy or of compounds of the formula Ib (≡ I with Q = Q 2 ) with R 20 = hydroxy, according to Claim 1, characterized in that that he
a) ein Cyclohexandion der Formel Va) a cyclohexanedione of formula V
wobei die Variablen R7 bis Ri2 die in Anspruch 1 angegebene Bedeutung haben,where the variables R 7 to R i2 have the meaning given in claim 1,
oderor
b) ein Pyrazol der Formel VIIIb) a pyrazole of the formula VIII
wobei die Variablen R2i bis R22 die in Anspruch 1 angegebene Bedeutung haben,where the variables R 2i to R 22 have the meaning given in claim 1,
mit einer aktivierten Phosphor-haltigen Benzoesäure der Formel IVα oder einer Phosphor-haltigen Benzoesäure der Formel IVß with an activated phosphorus-containing benzoic acid of the formula IVα or a phosphorus-containing benzoic acid of the formula IVß
wobei die Variablen X, R1 bis R4 und 1 die in Anspruch 1 genannte Bedeutung haben und L2 für eine nucleophil vergräng- bare Abgangsgruppe steht, acyliert und das Acylierungsprodukt ggf. in Gegenwart eines Katalysators umlagert.where the variables X, R 1 to R 4 and 1 have the meaning given in claim 1 and L 2 represents a nucleophilically extendable leaving group, acylated and the acylation product optionally rearranged in the presence of a catalyst.
Verfahren zur Herstellung von Verbindungen der Formel IbProcess for the preparation of compounds of formula Ib
(≡ I mit Q=Q2) mit R20 * Hydroxy gemäß Anspruch 1, dadurch gekennzeichnet, daß man ein metalliertes Pyrazol -Derivat der Formel VII, wobei M für Metall steht und R20 bis R22 die in Anspruch 1 genannte Bedeutung mit Ausnahme von R20 = Hydroxy haben, mit einem Phosphor-haltigen Benzoesäure-Derivat der Formel IVγ, wobei X, R bis R4 und 1 die in Anspruch 1 genannte Bedeutung haben und L3 für eine nucleophil verdräng- bare Abgangsgruppe steht, umsetzt.(≡ I with Q = Q 2 ) with R 20 * hydroxy according to claim 1, characterized in that a metallized pyrazole derivative of the formula VII, where M is metal and R 20 to R 22 has the meaning given in claim 1 Exception of R 20 = hydroxy, with a phosphorus-containing benzoic acid derivative of the formula IVγ, where X, R to R 4 and 1 have the meaning given in claim 1 and L 3 is a nucleophilically displaceable leaving group.
mit R20 * Hydroxy ivγ Ib mit R20 * Hydroxy with R 20 * hydroxy ivγ Ib with R 20 * hydroxy
Verfahren zur Herstellung von Phosphor-haltigen Benzoyl-Derivate der Formel Ib ( ≡ I mit Q=Q2) mit R20 = Hydroxy, gemäß Anspruch 1, dadurch gekennzeichnet, daß man ein Pyrazol der Formel VIII, in der die Variablen R2i und R22 die in An- spruch 1 genannte Bedeutung haben, oder ein Alkalisalz hiervon, Process for the preparation of phosphorus-containing benzoyl derivatives of the formula Ib (≡ I with Q = Q 2 ) with R 20 = hydroxy, according to Claim 1, characterized in that a pyrazole of the formula VIII in which the variables R 2i and R 22 has the meaning given in claim 1, or an alkali salt thereof,
mit einem Phosphor-haltigen Benzolderivat der Formel X, wobei die Variablen X, R1 bis R4 und 1 die in Anspruch 1 genannte Bedeutung haben und L4 für eine Abgangsgruppe steht .with a phosphorus-containing benzene derivative of the formula X, where the variables X, R 1 to R 4 and 1 have the meaning given in claim 1 and L 4 represents a leaving group.
in Gegenwart von Kohlenmonoxid, eines Katalysators sowie ei ner Base umsetzt.in the presence of carbon monoxide, a catalyst and a base.
Verfahren zur Herstellung von Phosphor-haltigen Benzoyl-Derivate der Formel Ic (≡ I mit Q=Q3) gemäß Anspruch 1, dadurch gekennzeichnet, daß man eine 1, 3 -Dicarbonylverbindung der Formel XIA process for the preparation of phosphorus-containing benzoyl derivatives of the formula Ic (≡ I with Q = Q 3 ) according to claim 1, characterized in that a 1,3-dicarbonyl compound of the formula XI
wobei die Variablen X, R1 bis R4, R23 und 1 die in Anspruch genannte Bedeutung haben und L5 für Cι-C6 -Alkoxy oder Di (Cι-C6 -alkyl) amino steht, mit Hydroxylamin umsetzt.where the variables X, R 1 to R 4 , R 23 and 1 have the meaning given in claim and L 5 is -C 6 -alkoxy or di (-C 6 -alkyl) amino, reacted with hydroxylamine.
Verfahren zur Herstellung von Phosphor-haltigen Benzoyl-Derivate der Formel Id ( = I mit Q=Q4) gemäß Anspruch 1, dadurch gekennzeichnet, daß man ein Cyanoketon XVII, Process for the preparation of phosphorus-containing benzoyl derivatives of the formula Id (= I with Q = Q 4 ) according to Claim 1, characterized in that a cyanoketone XVII,
wobei R25 die in Anspruch 1 genannte Bedeutung hat, mit einer aktivierten Phosphor-haltigen Benzoesäure IVα,where R 25 has the meaning given in claim 1, with an activated phosphorus-containing benzoic acid IVα,
wobei die Variablen X, R1 bis R4, R23 und 1 die in An- spruch 1 genannte Bedeutung haben und L2 für eine nucleophil verdrängbare Abgangsgruppe steht, in Gegenwart einer Base umsetzt.where the variables X, R 1 to R 4 , R 23 and 1 have the meaning given in claim 1 and L 2 represents a nucleophilically displaceable leaving group, in the presence of a base.
Mittel, enthaltend eine herbizid wirksame Menge mindestens eines Phosphor-haltigen Benzoyl -Derivates der Formel I oder eines landwirtschaftlich brauchbaren Salzes von I gemäß Anspruch 1, und für die Formulierung von Pflanzenschutzmitteln übliche Hilfsmittel.Agent containing a herbicidally effective amount of at least one phosphorus-containing benzoyl derivative of the formula I or an agriculturally useful salt of I according to claim 1, and auxiliaries customary for the formulation of crop protection agents.
Verfahren zur Herstellung von Mitteln gemäß Anspruch 17, dadurch gekennzeichnet, daß man eine herbizid wirksame Menge mindestens eines Phosphor-haltigen Benzoyl-Derivates der Formel I oder eines landwirtschaftlich brauchbaren Salzes von I gemäß Anspruch 1 und für die Formulierung von Pflanzenschutz- mittein übliche Hilfsmittel mischt.A process for the preparation of compositions according to claim 17, characterized in that a herbicidally effective amount of at least one phosphorus-containing benzoyl derivative of the formula I or an agriculturally useful salt of I according to claim 1 is mixed and auxiliaries customary for the formulation of crop protection agents .
Verfahren zur Bekämpfung von unerwünschtem Pflanzenwuchs, dadurch gekennzeichnet, daß man eine herbizid wirksame Menge mindestens eines Phosphor-haltigen Benzoyl -Derivates der For- mel I oder eines landwirtschaftlich brauchbaren Salzes von I gemäß Anspruch 1 auf Pflanzen, deren Lebensraum und/oder auf Samen einwirken läßt.Process for combating undesirable plant growth, characterized in that a herbicidally effective amount of at least one phosphorus-containing benzoyl derivative of the formula I or an agriculturally useful salt of I according to claim 1 acts on plants, their habitat and / or on seeds leaves.
Verwendung von Phosphor-haltigen Benzoyl -Derivates der For- mel I oder deren landwirtschaftlich brauchbaren Salze gemäßUse of phosphorus-containing benzoyl derivatives of the formula I or their agriculturally useful salts in accordance with
Anspruch 1 als Herbizide. Phosphor -haltigen Benzoesaure-Derivate der Formel IVClaim 1 as a herbicide. Phosphorus-containing benzoic acid derivatives of the formula IV
wobei die Variablen folgende Bedeutung haben:where the variables have the following meaning:
X Sauerstoff oder Schwefel;X oxygen or sulfur;
Ri,R2 Wasserstoff, Cι-C6 -Alkyl, C2-C6 -Alkenyl, C2-C6-Alki- nyl, Cι-C6 -Alkoxy, C3 -Cö-Alkenyloxy, C3 -C6 -Alkinyl - oxy, Mercapto, Ci-Cg-Alkylthio, C3-C6-Alkenylthio, C3-C6 -Alkinylthio, Amino, Cι-C6 -Alkylamino, Di- (Cι-C6-alkyl) amino, (Cι-C6 -Alkoxy) (Cι-C6-al- kyl) -amino, (C3-C6-Alkenyl) (Ci-Cβ-alkyl) amino, (C3-C6 -Alkinyl) (Cι-C6 -alkyl) amino, Di (C3-C6-alke- nyDamino oder Di- (C3-C6 -alkinyl) amino, wobei die genannten Alkyl-, Alkenyl- oder Alkinylreste par- tiell oder vollständig halogeniert sein können und/oder eine bis drei der folgenden Gruppen tragen können:R i, R 2 are hydrogen, C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 -Alki- nyl, Cι-C 6 -alkoxy, C 3 -C ö alkenyloxy, C 3 - C 6 -alkynyloxy, mercapto, C 1 -C 6 -alkylthio, C 3 -C 6 -alkenylthio, C 3 -C 6 -alkynylthio, amino, C 1 -C 6 -alkylamino, di- (-C 6 -alkyl) amino, (-C-C 6 -alkoxy) (Cι-C 6 -alkyl) -amino, (C 3 -C 6 -alkenyl) (Ci-Cβ-alkyl) amino, (C 3 -C 6 -alkynyl) (-C-C 6 -alkyl) amino, di (C 3 -C 6 -alkenyDamino or di- (C 3 -C 6 -alkynyl) amino), the alkyl, alkenyl or alkynyl radicals mentioned being partial or complete can be halogenated and / or can carry one to three of the following groups:
Nitro, Cyano, Cι-C4-Alkoxy, Cι-C4-Alkylthio, C1-C4 -Alkylsulfinyl, C1-C4 -Alkylsulfonyl, Di (Cι-C4-alkyl) -amino, Cι-C -Alkylcarbonyl,Nitro, cyano, C 4 -alkoxy, C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 -alkylsulfonyl, di (Cι-C4 alkyl) amino, Cι-C - Alkylcarbonyl,
C1-C4 -Alkoxycarbonyl, Phenyl oder Heterocyclyl, wobei die beiden letztgenannten Reste seinerseits partiell oder vollständig halogeniert sein können und/oder eine bis drei der foglenden Gruppen tra- gen können:C 1 -C 4 alkoxycarbonyl, phenyl or heterocyclyl, where the latter two radicals can in turn be partially or completely halogenated and / or can carry one to three of the following groups:
Nitro, Cyano, Cι-C4-Alkyl, C1-C4 -Halogenalkyl, C1-C4 -Alkoxy, C1-C4-Halogenalkoxy oder C1-C4-Alkoxycarbonyl;Nitro, cyano, C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 -haloalkoxy or C 1 -C 4 alkoxycarbonyl;
Phenoxy, das partiell oder vollständig halogeniert sein kann und/oder eine bis drei der folgenden Gruppen tragen kann:Phenoxy, which can be partially or completely halogenated and / or can carry one to three of the following groups:
Nitro, Cyano, C1-C4 -Alkyl, C1-C4 -Halogenalkyl, C1-C4 -Alkoxy, C1-C4-Halogenalkoxy oder C1-C4 -Alkoxy- carbonyl; oder Ri und R2 bilden gemeinsam eine -0- (CH2)m-0- , -0- (CH )m-S- , -S- (CH2)m-S-, -NR5- (CH2)m-NR5-, -O- (CH2) m-NR5- , -S- (CH2)m-NR5-, -(CH2)n-0-, - (CH2)n-S- oder - (CH )n-NR5 -Kette aus, die einen bis drei Reste aus folgender Gruppe tragen kann:Nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy or C 1 -C 4 alkoxycarbonyl; or R i and R 2 together form a -0- (CH 2 ) m -0-, -0- (CH) m -S-, -S- (CH 2 ) m -S-, -NR 5 - (CH 2 ) m -NR 5 -, -O- (CH 2 ) m -NR 5 -, -S- (CH 2 ) m -NR 5 -, - (CH 2 ) n -0-, - (CH 2 ) n - S or - (CH) n -NR 5 chain, which can carry one to three residues from the following group:
Halogen, Cyano, Cι-C4-Alkyl, C1-C4 -Halogenalkyl, C1-C4 -Alkoxy, C1-C4 -Alkoxycarbonyl oder Phenyl, das unsubstituiert ist oder partiell oder vollständig halogeniert ist und/oder eine bis drei der folgen- den Gruppen tragen kann:Halogen, cyano, -CC 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkoxycarbonyl or phenyl, which is unsubstituted or partially or fully halogenated and / or one can carry up to three of the following groups:
Nitro, Cyano, C1-C4 -Alkyl, C1-C4-Halogenalkyl, C1-C4 -Alkoxy, C1-C4 -Halogenalkoxy oder C1-C4 -Alkoxycarbonyl;;Nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy or C 1 -C 4 alkoxycarbonyl ;;
oderor
Ri und R2 bilden gemeinsam eine - (CH2)p-Kette, die durch Sauerstoff, Schwefel oder NR5 unterbrochen sein kann und/oder einen bis drei Reste aus folgender Gruppe tragen kann:R i and R 2 together form a - (CH 2 ) p chain, which can be interrupted by oxygen, sulfur or NR 5 and / or can carry one to three radicals from the following group:
Halogen, Cyano, C1-C4 -Alkyl, C1-C4 -Halogenalkyl, C1-C4 -Alkoxy, C1-C4 -Alkoxycarbonyl oder Phenyl, das unsubstituiert ist oder partiell oder vollständig halogeniert ist und/oder eine bis drei der folgen- den Gruppen tragen kann:Halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkoxycarbonyl or phenyl, which is unsubstituted or partially or completely halogenated and / or can carry one to three of the following groups:
Nitro, Cyano, C1-C4 -Alkyl, C1-C4 -Halogenalkyl, C1-C4 -Alkoxy, C3.-C4 -Halogenalkoxy oder C1-C4 -Alkoxycarbonyl;Nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 3 -C 4 haloalkoxy or C 1 -C 4 alkoxycarbonyl;
R3 Cyano, Halogen, Cι-C6 -Alkyl, Cι-C6 -Halogenalkyl,R 3 is cyano, halogen, Cι-C 6 -alkyl, C 6 haloalkyl,
Cx -C6 -Alkoxy-Cι-C6- lkyl, C -C6-Halogenalkoxy-Cι-C6- alkyl, Cx -C6 -Alkylthio-Cι-C6- alkyl, Ci -Cβ -Alkylsulfinyl -Ci -C6 -alkyl , Ci -C6 -Alkylsulfo- nyl-Cι-C6-alkyl, Ci-Cß-Alkylcarbonyl, Cι-C6-Alkoxy, C!-C6 -Halogenalkoxy, Cι-C6 -Aikylthio, Ci-Cδ-Haloge- nalkylthio, Cι-C6 -Alkylsulf inyl, Cι-C6 -Halogenal- kylsulfinyl, Ci -C6-Alkylsulfonyl, C3. -C6-Halogenal- kylsulfonyl, Aminosulfonyl, Ci-Cβ-Alkylaminosulfo- nyl, Di- (Ci-Cβ-alkyl) aminosulfonyl, (Ci-Cδ-Alkyl- sulfonyl) amino, (Cι-C6 -Halogenalkylsulfonyl) amino, Cx-C6 alkoxy-Cι-C 6 - lkyl, C-C6 haloalkoxy-Cι-C 6 - alkyl, C x -C 6 alkylthio-Cι-C 6 - alkyl, Ci -Cβ alkylsulfinyl -C -C 6 -alkyl, Ci -C 6 -alkylsulfonyl-Cι-C 6 -alkyl, Ci-C ß -alkylcarbonyl, Cι-C 6 -alkoxy, C ! -C 6 -haloalkoxy, -C-C 6 -alkylthio, Ci-C δ -halo-alkylthio, -C-C 6 -alkylsulfyl, Cι-C 6 -haloalkylsulfinyl, Ci -C 6 -alkylsulfonyl, C 3rd -C 6 -Halogenal- alkylsulfonyl, aminosulfonyl, Ci-Cβ-alkylaminosulfonyl, di- (Ci-Cβ-alkyl) aminosulfonyl, (Ci-C δ- alkylsulfonyl) amino, (Cι-C 6 -haloalkylsulfonyl) amino ,
N- (Ci-Cβ-Alkyl) -N- (Cι-C6- alkylsulfonyl) amino, N- (Cι-C6-Alkyl) -N- (Cχ-C6 -halogenalkylsulfo- nyl) amino, -P(=X)RiR2, Phenyl oder Heterocyclyl, wobei die beiden letztgenannten Reste partiell oder vollständig halogeniert sein können und/oder einen bis drei der folgenden Gruppen tragen können: Nitro, Cyano, C1-C4 -Alkyl, C1-C4 -Halogenalkyl, C1-C4 -Alkoxy, C1-C4 -Halogenalkoxy oder C1-C4-Alkoxycarbonyl ;N- (Ci-Cβ-alkyl) -N- (-C-C 6 -alkylsulfonyl) amino, N- (Cι-C 6 -alkyl) -N- (Cχ-C 6 -haloalkylsulfonyl) amino, -P ( = X) R i R 2 , phenyl or heterocyclyl, where the latter two radicals can be partially or completely halogenated and / or can carry one to three of the following groups: Nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy or C 1 -C 4 alkoxycarbonyl;
R4 Nitro, Cyano, Halogen, Cι-C6 -Alkyl, Cι-C6 -Alkoxy,R 4 nitro, cyano, halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy,
Ci-Cβ-Alkylthio, Ci-Cβ -Alkylsulfinyl oder Cι-C6-Al- kylsulfonyl;Ci-Cβ-alkylthio, Ci-Cβ-alkylsulfinyl or -C-C 6 alkylsulfonyl;
R5 Wasserstoff, Cι-C6 -Alkyl, Cι-C6 -Halogenalkyl oder Ci -C6-Alkoxy;R 5 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl or C 1 -C 6 -alkoxy;
1 0 , 1 oder 2 ;1 0, 1 or 2;
m 2 , 3 oder 4 ;m 2, 3 or 4;
n 3 , 4 oder 5 ;n 3, 4 or 5;
P 4 , 5 oder 6 ;P 4, 5 or 6;
R26 abhydrolysi R 26 abhydrolysi
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