WO2015007662A1 - Azin-2-one-3-carboxamides and their use as herbicides - Google Patents

Azin-2-one-3-carboxamides and their use as herbicides Download PDF

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Publication number
WO2015007662A1
WO2015007662A1 PCT/EP2014/064985 EP2014064985W WO2015007662A1 WO 2015007662 A1 WO2015007662 A1 WO 2015007662A1 EP 2014064985 W EP2014064985 W EP 2014064985W WO 2015007662 A1 WO2015007662 A1 WO 2015007662A1
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alkyl
alkoxy
halogeno
cycloalkyl
halo
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PCT/EP2014/064985
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German (de)
French (fr)
Inventor
Ralf Braun
Christian Waldraff
Jörg Tiebes
Ines Heinemann
Arnim Köhn
Alfred Angermann
Hartmut Ahrens
Stephen David Lindell
Dirk Schmutzler
Hansjörg Dietrich
Christopher Hugh Rosinger
Elmar Gatzweiler
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Bayer Cropscience Ag
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Publication of WO2015007662A1 publication Critical patent/WO2015007662A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the invention relates to the technical field of herbicides, in particular that of herbicides for the selective control of weeds and weeds in
  • WO 2010/126914 A1 discloses 1-benzyl-N- (5-methyl-1, 3,4-oxadiazol-2-yl) -2-oxo-1,2-dihydropyridine-3-carboxamide and 1-benzyl-2-yl oxo-N- (5-phenyl-1,3,4-oxadiazol-2-yl) -1,2-dihydropyridine-3-carboxamide as pharmacologically active compounds.
  • azin-2-one-3-carboxamides are particularly suitable as herbicides.
  • An object of the present invention are thus azin-2-one-3-carboxamides of the formula (I) or salts thereof
  • R 1 represents (C 1 -C 10) -alkyl, (C 2 -C 10) -alkenyl, (C 2 -C 10) -alkynyl, halogeno (C 1 -C 10) -alkyl, halogeno (C 2 -C 10) -alkenyl, halogen (C 2 -C 10) -alkynyl, (C 3 -C 10) -cycloalkyl, halogeno (C 3 -C 10) -cycloalkyl, (C 1 -C 6 ) -alkyl (C 3 -C 7 ) -cycloalkyl, ( C 3 -C 7 ) -cycloalkyl (C 1 -C 6 ) -alkyl, (C 3 -C 7 ) -cycloalkyl- (C 3 -C 7 ) -cycloalkyl- (C 3 -C 7 ) -cycloalkyl- (
  • R 1 is phenyl, phenylsulfonyl, W 1 - (phenyl), W 1 - (O-phenyl), W 1 - (S-phenyl), W 1 - (SO 2 -phenyl), W 2 - (SO 2 CH 2 Phenyl) or W 2 - (SCH 2 -phenyl), where the phenyl rings of the eight abovementioned radicals each carry s substituents R 6 ,
  • X 1 is N or CR 2a
  • X 2 is N or CR 2b
  • R 2a is phenyl or W 3 - (phenyl), wherein the phenyl rings of the two radicals mentioned above each carry s substituents R 6 , or
  • R 3 is (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, where these radicals are each represented by s radicals from the group consisting of halogen, cyano, hydroxyl, Nitro, SiR 10 3 , PO (OR 10 ) 2 , S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy,
  • R 3a is hydrogen, (Ci-C 6) -alkyl, (C2-C6) alkenyl, (C2-C6) -alkynyl, (C 3 -C 6) - cycloalkyl or (C3-C6) cycloalkyl (C 1 -C 6) -alkyl or phenyl,
  • R 3b represents (Ci-C 6) -alkyl, (C 2 -C 6) -alkenyl or (C2-C6) -alkynyl, (C3-C6) -cycloalkyl or (C3-C6) cycloalkyl (Ci -C 6 ) -alkyl or phenyl,
  • R 4 represents hydrogen, (Ci-C 6) -alkyl, (C 3 -C 7) -cycloalkyl, halo (Ci-C 6) alkyl, (Ci-Ce) alkoxy, halo (Ci- C 6) alkoxy, (C2-C6) alkenyl, (C2-C6) alkenyloxy, (C 2 -C 6) - haloalkenyl, (C2-C6) -alkynyl, (C2-C6) - alkynyloxy, (C2-C6) haloalkynyl, (Ci-C6) - alkoxy- (Ci-C6) alkyl, cyano, nitro, methylsulphenyl, methylsulphinyl, methylsulphonyl, acetylamino, benzoylamino, methoxycarbonyl, ethoxycarbonyl,
  • Methylaminocarbonyl dimethylaminocarbonyl, methoxymethyl, or
  • R 5 represents hydrogen, (Ci-C 6) -alkyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, CH 2 R 5a, (C 3 - C 7) cycloalkyl, halo ( Ci-C 6) alkyl, (C2-C6) alkenyl, halo (C2-C6) alkenyl, (C2 - Ce) alkynyl, halo (C2-C6) alkynyl, OR 6, NHR 6 , methoxycarbonyl, ethoxycarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, methylcarbonyl,
  • Trifluoromethylcarbonyl dimethylamino, acetylamino, methylsulfenyl, methylsulfinyl, methylsulfonyl or in each case by p radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 3 -C 4 ) -alkyl C 6 ) -cycloalkyl, S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkoxy- Ci-C) -alkyl
  • R 5a represents acetoxy, acetamido, N-methylacetamido, benzoyloxy, benzamido, N-methylbenzamido, methoxycarbonyl, ethoxycarbonyl, benzoyl, methylcarbonyl, Piperidinylcarbonyl, morpholinylcarbonyl, trifluoromethylcarbonyl, aminocarbonyl, methylaminocarbonyl, dimethylanninocarbonyl, (C 1 -C 6) -alkoxy, (C 3 -C 6) -cycloalkyl or in each case by p radicals from the group consisting of methyl, ethyl, methoxy,
  • Y is O or S
  • W 1 represents (Ci-Cio) alkylene, (C 2 -C 6) -alkenylene or (C2-C6) alkynylene
  • W 2, W 3 and W 4 each represents (Ci-Cio) alkylene
  • G means each consisting of halogen, nitro, cyano substituted by s radicals selected from the group (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C3-C6) -cycloalkyl, S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy and (C 1 -C 6 ) -alkoxy- (C 1 -C 4 ) -alkyl-substituted heteroaryl or heterocyclyl, where heterocyclyl carries n oxo groups,
  • alkyl radicals having more than two carbon atoms may be straight-chain or branched.
  • Alkyl radicals mean e.g. Methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i-hexyl and 1, 3-dimethylbutyl.
  • AI means kenyl, e.g. Allyl, 1-methylprop-2-en-1-yl,
  • Alkynyl means e.g. Propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methyl-but-3-yn-1-yl.
  • the multiple bond can each be in any position of the unsaturated radical.
  • Cycloalkyl means a carbocyclic saturated ring system having three to six C atoms, e.g. Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
  • cycloalkenyl is a monocyclic alkenyl group having three to six carbon ring members, e.g. Cyclopropenyl, cyclobutenyl,
  • Cyclopentenyl and cyclohexenyl, wherein the double bond may be in any position.
  • (C 1 -C 10) -alkylene accordingly denotes a methylene, ethylene, in each case unbranched propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene or decylene group.
  • Halogen is fluorine, chlorine, bromine or iodine.
  • Heterocyclyl means a saturated, partially saturated or fully unsaturated cyclic radical containing from 3 to 6 ring atoms, of which from 1 to 4 are from the group oxygen, nitrogen and sulfur, and additionally by a Benzoring can be annealed.
  • heterocyclyl is piperidinyl, pyrrolidinyl, tetrahydrofuranyl, dihydrofuranyl and oxetanyl,
  • Heteroaryl means an aromatic cyclic radical containing from 3 to 6 ring atoms, of which from 1 to 4 are from the group consisting of oxygen, nitrogen and sulfur, and may additionally be fused by a benzene ring.
  • heteroaryl is benzimidazol-2-yl, furanyl, imidazolyl, isoxazolyl, isothiazolyl, oxazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridinyl, benzisoxazolyl, thiazolyl, pyrrolyl, pyrazolyl, thiophenyl, 1, 2,3-oxadiazolyl, 1, 2 4-oxadiazolyl, 1, 2,5-oxadiazolyl, 1, 3,4-oxadiazolyl, 1, 2,4-triazolyl, 1, 2,3-triazolyl, 1, 2,5-triazolyl, 1, 3,4- Triazolyl, 1, 2,4-triazolyl, 1, 2,4-thiadiazolyl, 1, 3,4-thiadiazolyl, 1, 2,3-thiadiazolyl, 1, 2,5-thiadiazolyl, 2H-1,2,3, 4-tetrazolyl,
  • the compounds of the general formula (I) can exist as stereoisomers. For example, if one or more asymmetric carbon atoms are present, then enantiomers and
  • stereoisomers can be prepared by using stereoselective reactions using optically active starting materials and / or
  • the invention also relates to all stereoisomers and mixtures thereof which are of the general formula (I), but not specifically defined.
  • the compounds of the invention may also occur as geometric isomers (E / Z isomers) due to the oxime ether structure.
  • the invention also relates to all E / Z isomers and mixtures thereof, which are of the general formula (I), but not specifically defined.
  • the compounds of formula (I) can form salts.
  • Suitable bases are organic amines, such as trialkylamines, morpholine, piperidine or pyridine, and also ammonium, alkali metal or alkaline earth metal hydroxides, carbonates and bicarbonates, in particular sodium and potassium hydroxide, sodium and potassium carbonate and sodium and potassium bicarbonate.
  • salts are compounds in which the acidic hydrogen is replaced by an agriculturally suitable cation, for example metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or else ammonium salts, salts with organic amines or quaternary ammonium salts
  • metal salts in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or else ammonium salts, salts with organic amines or quaternary ammonium salts
  • R 1 to R '" each independently of one another represent an organic radical, in particular alkyl, aryl, aralkyl or alkylaryl.
  • suitable are also alkylsulfonium and alkylsulfoxonium salts, such as (Ci -C 4) - trialkylsulfonium and (Ci-C 4) -Trialkylsulfoxoniumsalze.
  • the compounds of formula (I) can be prepared by addition of a suitable organic compound.
  • inorganic or organic acid such as mineral acids such as HCl, HBr, H 2 SO 4, H3PO 4 or HNO 3, or organic acids, eg.
  • carboxylic acids such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or sulfonic acids such as p-toluenesulfonic acid to form a basic group such as amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino, salts.
  • These salts then contain the conjugate base of the acid as an anion.
  • R 1 represents (C 1 -C 10) -alkyl, (C 2 -C 10) -alkenyl, (C 2 -C 10) -alkynyl, halogeno (C 1 -C 10) -alkyl, halogeno (C 2 -C 10) -alkenyl, halogen - (C 2 -C 10) -alkynyl, (C 3 -C 10) -cycloalkyl, halogeno (C 3 -C 10) -cycloalkyl, (C 1 -C 6 ) -alkyl (C 3 -C 7 ) -cycloalkyl, ( C 3 -C 7 ) -cycloalkyl (C 1 -C 6 ) -alkyl, (C 3 -C 7 ) -cycloalkyl- (C 3 -C 7 ) -cycloalkyl, halogeno (C 3 -C 7 ) -cycl
  • R 1 is phenyl, phenylsulfonyl, W 1 - (phenyl), W 1 - (O-phenyl), W 1 - (S-phenyl), W 1 - (SO 2 -phenyl), W 2 - (SO 2 CH 2 Phenyl) or W 2 - (SCH 2 -phenyl), where the phenyl rings of the eight abovementioned radicals each carry s substituents R 6 , or X 1 denotes N or CR 2a ,
  • X 2 is N or CR 2b
  • R 2a is phenyl or W 3 - (phenyl), wherein the phenyl rings of the two radicals mentioned above each carry s substituents R 6 , or
  • R 2b is hydrogen, halogen, (C 1 -C 4) -alkyl or (C 1 -C 4) -alkoxy, 1, Q 2 , Q 3 or Q 4 ,
  • R 3 is (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, where these radicals are each represented by s radicals from the group consisting of halogen, cyano, nitro, S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy, (C 3 -C 6 ) -cycloalkyl, heteroaryl, heterocyclic or phenyl in which the 4 last-mentioned radicals are each substituted by p radicals from the group consisting of methyl, ethyl, methoxy, trifluoromethyl, cyano and halogen, and where heterocyclyl carries n oxo groups, or R 3 is phenyl, each being represented by p radicals from
  • R 4 is (Ci-C 6) -alkyl, (C 3 -C 7) -cycloalkyl, halo (Ci-C 6) alkyl, (Ci-C 6) - alkoxy, halo (Ci-C6 ) -alkoxy, cyano, nitro, methylsulfenyl, methylsulfinyl,
  • R 5 represents hydrogen, (Ci-C 6) -alkyl, (C 3 -C 7) cycloalkyl, halo (Ci-C 6) alkyl, (C3-C7) cycloalkylmethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl,
  • W 1 denotes (C 1 -C 10) -alkylene, (C 2 -C 6 ) -alkenylene or (C 2 -C 6 ) -alkynylene, W 2 , W 3 and W 4 are each (C 1 -C 10) -alkylene,
  • G represents in each case by s radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy and (C 1 -C 6 ) -alkoxy- (C 1 -C 4 ) -alkyl-substituted heteroaryl or heterocyclyl, where heterocyclyl carries n oxo groups, n denotes 0, 1 or 2, p denotes 0, 1, 2 or 3, s denotes 0, 1, 2, 3, 4 or 5, t denotes 0 or 1.
  • R 1 represents (C 1 -C 10) -alkyl, (C 2 -C 10) -alkenyl, (C 2 -C 10) -alkynyl, halogeno (C 1 -C 10) -alkyl, halogeno (C 2 -C 10) -alkenyl, halogen - (C 2 -C 10) -alkynyl, (C 3 -C 10) -cycloalkyl, halo (C 3 -C 10) -cycloalkyl, (C 1 -C 4 ) -alkyl (C 3 -C 7 ) -cycloalkyl, (C 3 -C 4 ) cycloalkyl, (C 3 -C 10) -cycloalkyl; 7 ) -cycloalkyl- (Ci-C 6 ) -alkyl, (C 3 -C 7 ) -cycloalkyl- (C 3 -C 7
  • R 1 is phenyl, W 1 - (phenyl), where the phenyl rings each carry s substituents R 6 ,
  • X 1 is N or CR 2a
  • X 2 is N or CR 2b
  • R 2a is phenyl or W 3 - (phenyl), wherein the phenyl rings of the two radicals mentioned above each carry s substituents R 6 , or
  • Q is a radical Q 1 , Q 2 , Q 3 or Q 4
  • R 3 represents in each case by s radicals from the group consisting of halogen, cyano, nitro, S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy and halogen- (C 1 -C 6 ) - alkoxy-substituted (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl or (C 2 -C 8 ) -alkynyl,
  • R 4 is (C 1 -C 6 ) -alkyl, (C 3 -C 7 ) -cycloalkyl, halogeno (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) alkoxy, cyano, nitro, methylsulfenyl, methylsulfinyl,
  • R 5 represents Wassetrstoff, (Ci-C 6) -alkyl, (C 3 -C 7) cycloalkyl, halo (Ci-C 6) - alkyl, (C3-C7) cycloalkylmethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, acetylmethyl, Methoxymethyl, methoxyethyl, benzyl, pyrazine-2-yl, furan-2-yl,
  • R 6 is halogen, cyano, nitro, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, halogeno (C 1 -C 6 ) -alkyl, (C 3 -C 4 ) -alkyl, C 6 ) -cycloalkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkylthio, (C 1 -C 6 ) -alkylsulfinyl, (C 1 -C 6 -alkylsulfonyl, Phenyl, methylene dioxo,
  • W 1 is (C 1 -C 10) -alkylene
  • W 2 , W 3 and W 4 are each (C 1 -C 10) -alkylene
  • G is in each case represented by s radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 3 ) -alkyl, cyclopropyl, S (O) n - (C 1 -C 3 ) -Alkyl, (Ci-C) - alkoxy, halogen- (Ci-C 4 ) -alkoxy and (Ci-C 4 ) -alkoxy- (Ci-C 4 ) -alkyl substituted
  • Heteroaryl or heterocyclyl wherein heterocyclyl carries n oxo groups, n means 0, 1 or 2, p means 0, 1, 2 or 3, s means 0, 1, 2, 3, 4 or 5.
  • azin-2-one-3-carboxylic acid chlorides (II) or their underlying azin-2-one-3-carboxylic acids (III) may be e.g. be prepared according to the methods described in WO 2012/148622 A1.
  • the listed equipment leads to a modular procedure, in which the individual work steps are automated, but between the work steps, manual operations must be performed.
  • This can be circumvented by the use of partially or fully integrated automation systems in which the respective automation modules are operated, for example, by robots.
  • Such automation systems can be obtained, for example, from Caliper, Hopkinton, MA 01748, USA.
  • Synthesis methods allow a number of protocols known from the literature, which in turn can be carried out manually or automatically.
  • the reactions can be carried out, for example, by means of IRORI technology in microreactors (microreactors) from Nexus Biosystems, 12140 Community Road, Poway, CA92064, USA.
  • the preparation according to the methods described herein provides compounds of formula (I) and their salts in the form of substance collections called libraries.
  • the present invention also provides libraries containing at least two compounds of formula (I) and their salts.
  • the compounds of the invention have an excellent herbicidal
  • Harmful plants that drive off rhizomes, rhizomes or other permanent organs are well detected by the active ingredients.
  • the present invention therefore also provides a method for controlling unwanted plants or for regulating the growth of plants, preferably in plant crops, wherein one or more of the present invention
  • Compound (s) on the plants e.g., weeds such as mono- or dicotyledons
  • the seeds eg grains, seeds or vegetative propagules such as tubers or sprout parts with buds
  • the area on which the plants grow eg the acreage
  • the compounds according to the invention can be applied, for example, in pre-sowing (optionally also by incorporation into the soil), pre-emergence or postemergence process.
  • some representatives of the monocotyledonous and dicotyledonous weed flora may be mentioned which control the compounds according to the invention without being restricted to certain species.
  • the compounds according to the invention are applied to the surface of the earth prior to germination, either the emergence of the weed seedlings is completely prevented or the weeds grow up to the cotyledon stage, but then stop their growth and finally die after three to four weeks
  • the compounds of the present invention have excellent herbicidal activity against mono- and dicotyledonous weeds, crops of economically important crops, e.g. dicotyledonous cultures of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium,
  • Crops such as agricultural crops or ornamental plantings.
  • the active compounds can also be used to control harmful plants in crops of genetically engineered or conventional mutagenized plants.
  • the transgenic plants are usually characterized by particular advantageous properties, for example by resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Other special special traits for example by resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Properties relate to e.g. the crop in terms of quantity, quality, shelf life, composition and special ingredients.
  • transgenic plants with increased starch content or altered quality of the starch or those with other fatty acid composition of the crop are known.
  • transgenic cultures Preferred with respect to transgenic cultures is the use of the compounds of the invention in economically important transgenic crops of useful and
  • Ornamental plants eg of cereals such as wheat, barley, rye, oats, millet, rice and maize or also crops of sugar beet, cotton, soya, rapeseed, potato, cassava, Tomato, pea and other vegetables.
  • the compounds of the invention as herbicides in
  • Crop plants are used, which are resistant to the phytotoxic effects of herbicides or have been made genetically resistant.
  • Glufosinate see, for example, EP-A-0242236, EP-A-242246) or glyphosate
  • transgenic crops for example cotton, with the ability
  • Bacillus thuringiensis toxins Bacillus thuringiensis toxins (Bt toxins) to produce, which the
  • transgenic crops characterized by a combination z.
  • nucleic acid molecules can be used in any genetic manipulations.
  • nucleic acid molecules can be used in any genetic manipulations.
  • Plasmids are introduced which allow mutagenesis or a sequence change by recombination of DNA sequences. With the help of standard methods z. For example, base substitutions are made, partial sequences are removed, or natural or synthetic sequences are added.
  • adapters or linkers can be attached to the fragments, see, for example, US Pat. Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2 Ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY, or Winnacker "Gene and Clones", VCH Weinheim 2nd edition, 1996
  • the production of plant cells having a reduced activity of a gene product can be achieved, for example, by the expression of at least one
  • DNA molecules may be used which comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules which comprise only parts of the coding sequence, which parts must be long enough to be present in the cells to cause an antisense effect. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but are not completely identical.
  • the synthesized protein may be located in any compartment of the plant cell. But to achieve the localization in a particular compartment, z.
  • the coding region can be linked to DNA sequences that ensure localization in a particular compartment. Such sequences are the
  • Organelles of the plant cells take place.
  • the transgenic plant cells can be regenerated to whole plants by known techniques.
  • the transgenic plants may, in principle, be plants of any plant species, that is, both monocotyledonous and dicotyledonous plants.
  • transgenic plants are available, the altered properties by
  • the compounds of the invention can be used in transgenic cultures which are resistant to growth factors, such as. B. Dicamba or against
  • Herbicides containing essential plant enzymes e.g. As acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or Hydroxyphenylpyruvat dioxygenases (HPPD) inhibit or herbicides from the group of sulfonylureas, the glyphosate, glufosinate or benzoylisoxazole and analogues, resistant.
  • ALS acetolactate synthases
  • EPSP synthases glutamine synthases
  • HPPD Hydroxyphenylpyruvat dioxygenases
  • Harmful plants often have effects that are specific for application in the particular transgenic culture, such as altered or specially extended weed spectrum that can be controlled
  • the invention therefore also relates to the use of the compounds according to the invention as herbicides for controlling harmful plants in transgenic
  • the compounds of the invention may be in the form of wettable powders
  • the invention therefore also relates to herbicidal and plant growth-regulating agents which contain the compounds according to the invention.
  • the compounds according to the invention can be formulated in various ways, depending on which biological and / or chemical-physical parameters are predetermined. Possible formulation options are, for example: wettable powder (WP), water-soluble powders (SP), water-soluble concentrates,
  • EC emulsifiable concentrates
  • EW emulsions
  • Water-in-oil emulsions sprayable solutions, suspension concentrates (SC), oil- or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusts (DP), mordants, granules for spreading and soil application, granules (GR) in the form of micro, spray, elevator and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG),
  • the necessary formulation auxiliaries such as inert materials, surfactants, solvents and other additives are also known and are, for example
  • Injectable powders are preparations which are uniformly dispersible in water and contain surfactants of the ionic and / or nonionic type (wetting agents, dispersants) in addition to the active ingredient except a diluent or inert substance.
  • polyoxyethylated alkylphenols polyoxethylated fatty alcohols, polyoxethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate,
  • the herbicidal active compounds are finely ground, for example, in customary apparatus such as hammer mills, blower mills and air-jet mills and mixed simultaneously or subsequently with the formulation auxiliaries.
  • Emulsifiable concentrates are made by dissolving the active ingredient in one
  • organic solvents e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents with the addition of one or more surfactants of ionic and / or nonionic type (emulsifiers).
  • emulsifiers which may be used are: alkylarylsulfonic acid calcium salts, such as
  • Ca-dodecylbenzenesulfonate or nonionic emulsifiers such as
  • Fatty acid polyglycol esters alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers,
  • Propylene oxide-ethylene oxide condensation products alkyl polyethers, sorbitan esters such as For example, sorbitan fatty acid esters or Polyoxethylenensorbitanester such as
  • Dusts are obtained by milling the active ingredient with finely divided solids, e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • finely divided solids e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • Suspension concentrates may be water or oil based. They can be prepared, for example, by wet grinding using commercially available bead mills and, if appropriate, addition of surfactants, as described, for example, in US Pat. upstairs with the others
  • Emulsions e.g. Oil-in-water emulsions (EW) can be prepared, for example, by means of stirrers, colloid mills and / or static mixers using aqueous organic solvents and optionally surfactants, as described e.g. listed above for the other formulation types.
  • EW Oil-in-water emulsions
  • Granules can be prepared either by spraying the active ingredient on adsorptive, granulated inert material or by applying
  • Active substance concentrates by means of adhesives, e.g. Polyvinyl alcohol, polyacrylic acid sodium or mineral oils, on the surface of carriers such as sand, kaolinites or granulated inert material. It is also possible to granulate suitable active ingredients in the manner customary for the production of fertilizer granules, if desired in admixture with fertilizers.
  • adhesives e.g. Polyvinyl alcohol, polyacrylic acid sodium or mineral oils
  • carriers such as sand, kaolinites or granulated inert material. It is also possible to granulate suitable active ingredients in the manner customary for the production of fertilizer granules, if desired in admixture with fertilizers.
  • Water-dispersible granules are generally prepared by the usual methods such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
  • spray drying fluidized bed granulation
  • plate granulation mixing with high-speed mixers and extrusion without solid inert material.
  • the agrochemical preparations generally contain from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of compounds according to the invention.
  • the drug concentration is e.g. about 10 to 90 wt .-%, the balance to 100 wt .-% consists of conventional formulation ingredients.
  • the active ingredient concentration may be about 1 to 90, preferably 5 to 80 wt .-%.
  • Dust-like formulations contain 1 to 30 wt .-% of active ingredient, preferably usually 5 to 20 wt .-% of active ingredient, sprayable solutions contain about 0.05 to 80, preferably 2 to 50 wt .-% of active ingredient.
  • the active ingredient content depends, in part, on whether the active compound is liquid or solid and which
  • Granulation aids, fillers, etc. are used. In the water
  • the content of active ingredient is for example between 1 and 95 wt .-%, preferably between 10 and 80 wt .-%.
  • the active substance formulations mentioned optionally contain the customary adhesive, wetting, dispersing, emulsifying, penetrating, preserving,
  • Evaporation inhibitors and pH and viscosity affecting agents On the basis of these formulations, it is also possible to prepare combinations with other pesticide-active substances, such as, for example, insecticides, acaricides, herbicides, fungicides, and with safeners, fertilizers and / or growth regulators, for example in the form of a ready-to-use formulation or as a tank mix.
  • pesticide-active substances such as, for example, insecticides, acaricides, herbicides, fungicides, and with safeners, fertilizers and / or growth regulators
  • the formulations present in commercially available form are optionally diluted in customary manner, for example in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules by means of water. Dust-like preparations, ground or scattered granules and sprayable solutions are usually no longer before use with other inert Diluted substances.
  • the type of herbicide used u.a. varies the required application rate of the compounds of formula (I). It can vary within wide limits, e.g. between 0.001 and 1.0 kg / ha or more of active substance, but is preferably between 0.005 and 750 g / ha.
  • Table 1 Compounds of the invention of the general formula (I) wherein Q is Q 1 , R 3 is methyl, wherein X 1 is CR 2a and X 2 is CR 2b , and Y is oxygen.
  • a dust is obtained by mixing 10 parts by weight of a compound of formula (I) and / or salts thereof and 90 parts by weight of talc as an inert material and comminuting in a hammer mill.
  • a wettable powder easily dispersible in water is obtained by adding 25 parts by weight of a compound of formula (I) and / or its salts, 64 parts by weight of kaolin-containing quartz as inert material, 10 parts by weight
  • a dispersion concentrate readily dispersible in water is obtained by reacting 20 parts by weight of a compound of the formula (I) and / or salts thereof with 6 parts by weight of alkylphenol polyglycol ether ( ⁇ Triton X 207), 3 parts by weight
  • Mineral oil (boiling range, for example, about 255 to about 277 C) mixed and ground in a ball mill to a fineness of less than 5 microns.
  • An emulsifiable concentrate is obtained from 15 parts by weight of a
  • a water-dispersible granules are obtained by
  • a water-dispersible granule is also obtained by
  • the compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then used as aqueous suspension or
  • the compound No. 2-1 at a rate of 0.32 kg of active ingredient or less per hectare showed a very good effect (80% to 100% herbicidal activity) against harmful plants such as Veronica persica or Stellaria media.
  • compounds according to the invention leave gramineous crops such as barley, wheat, rye, millet, maize or rice in the pre-emergence process practically undamaged even at high doses of active ingredient.
  • some substances also protect dicotyledonous crops such as soybeans, cotton, canola, sugar beet or potatoes.
  • Some of the compounds according to the invention show a high selectivity and are therefore suitable in the pre-emergence process for controlling undesired plant growth in agricultural crops. 2. Herbicidal action against harmful plants in postemergence
  • the compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then used as aqueous suspension or

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Abstract

Disclosed are azin-2-one-3-carboxamides of general formula (I) as herbicides. In said formula (I) Y and Z represent a chalcogen, X1 and X2 represent nitrogen, R1 and R2 represent groups such as hydrogen, organic groups such as alkyl and other groups such as halogen. Q represents an azolylcarbamoyl group.

Description

Azin-2-on-3-carboxamide und ihre Verwendung als Herbizide  Azin-2-one-3-carboxamides and their use as herbicides
Beschreibung description
Die Erfindung betrifft das technische Gebiet der Herbizide, insbesondere das der Herbizide zur selektiven Bekämpfung von Unkräutern und Ungräsern in The invention relates to the technical field of herbicides, in particular that of herbicides for the selective control of weeds and weeds in
Nutzpflanzenkulturen. Crops of useful plants.
WO 2010/126914 A1 offenbart 1 -Benzyl-N-(5-methyl-1 ,3,4-oxadiazol-2-yl)-2-oxo-1 ,2- dihydropyridin-3-carboxamid und 1 -Benzyl-2-oxo-N-(5-phenyl-1 ,3,4-oxadiazol-2-yl)- 1 ,2-dihydropyridin-3-carboxamid als pharmakologisch wirksame Verbindungen. WO 2010/126914 A1 discloses 1-benzyl-N- (5-methyl-1, 3,4-oxadiazol-2-yl) -2-oxo-1,2-dihydropyridine-3-carboxamide and 1-benzyl-2-yl oxo-N- (5-phenyl-1,3,4-oxadiazol-2-yl) -1,2-dihydropyridine-3-carboxamide as pharmacologically active compounds.
Aus WO2012148622 sind u. a. Pyrazin-2-on-3-carbonylcyclohexandione und Pyrazin- 2-on-3-carbonylpyrazole als Herbizide beschrieben. Aus WO2013139760 sind u. a. herbizid wirksame Pyridazin-3-on-4-carboxamide bekannt. EP 2 562 174 A1 offenbart u. a. Pyrimid-4-on-5-carboxamide und Pyrid-2-on-3-carboxamide als Herbizide. Die aus diesen Schriften bekannten Verbindungen weisen jedoch nicht immer eine ausreichende herbizide Wirkung und/oder Verträglichkeit gegenüber Kulturpflanzen auf. From WO2012148622 u. a. Pyrazine-2-one-3-carbonylcyclohexandione and pyrazine-2-one-3-carbonylpyrazole described as herbicides. From WO2013139760 u. a. herbicidally active pyridazin-3-one-4-carboxamides known. EP 2 562 174 A1 discloses u. a. Pyrimid-4-one-5-carboxamides and pyrid-2-one-3-carboxamides as herbicides. However, the compounds known from these publications do not always have a sufficient herbicidal activity and / or compatibility with crop plants.
Es wurde nun gefunden, dass Azin-2-on-3-carboxamide als Herbizide besonders gut geeignet sind. It has now been found that azin-2-one-3-carboxamides are particularly suitable as herbicides.
Ein Gegenstand der vorliegenden Erfindung sind somit Azin-2-on-3-carboxamide der Formel (I) oder deren Salze An object of the present invention are thus azin-2-one-3-carboxamides of the formula (I) or salts thereof
Figure imgf000002_0001
worin R1 bedeutet (Ci-Cio)-Alkyl, (C2-Cio)-Alkenyl, (C2-Cio)-Alkinyl, Halogen-(Ci-Cio)- alkyl, Halogen-(C2-Cio)-alkenyl, Halogen-(C2-Cio)-alkinyl, (C3-Cio)-Cycloalkyl, Halogen- (C3-Cio)-cycloal kyl , (Ci -C )-Al kyl-(C3-C7)-cycloal kyl , (C3-C7)-Cycloal kyl-(Ci -C6)-al kyl , (C3-C7)-Cycloalkyl-(C3-C7)-cycloalkyl, Halogen-(C3-C7)-cycloalkyl-(Ci-C6)-alkyl, (Ci-C6)- Alkyl-(C3-C7)-cycloalkyl-(Ci-C6)-alkyl, (C3-Ci2)-Cycloalkenyl, Halogen-(C3-Ci2)- cycloalkenyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(C2-C6)-alkenyl, (Ci-C6)- Al kyl-(C3-C7)-cycloal kyl , (Ci -C6)-Al koxy-(C3-C7)-cycloal kyl , (C3-C7)-Cycloal koxy-(Ci - C6)-al kyl , (C3-C7)-Cycloal koxy-(Ci -C6)-al koxy-(Ci -C6)-al kyl , (Ci -C6)-Al koxy-(Ci -C6)- alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkylthio-(Ci-C6)-alkyl, (Ci-C6)-Alkylsulfinyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylsulfonyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylamino-(Ci-C6)-alkyl, Di-(Ci-Ce)- alkylamino-(Ci-C6)-alkyl, Halogen-(Ci-C6)-alkylamino-(Ci-C6)-alkyl, (C3-C7)- Cycloalkylamino-(Ci-C6)-alkyl, (Ci-C6)-Alkyl-carbonyl, Halogen-(Ci-C6)-alkyl-carbonyl, (C3-C7)-Cycloal kyl-carbonyl , (Ci -ΟΘ)-ΑΙ koxy-carbonyl , (C3-C7)-Cycloal koxy-carbonyl , (C3-C7)-Cycloalkyl-(Ci-C6)-alkoxy-carbonyl, (Ci-C6)-Alkylamino-carbonyl, Di-(Ci-Ce)- alkylamino-carbonyl, (C3-C7)-Cycloalkylamino-carbonyl, Cyano-(Ci-C6)-alkyl, Hydroxy- (Ci-C6)-alkyl, (C3-C7)-Cycloalkenyl-(Ci-C6)-alkyl, Halogen-(Ci-C6)-alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-halogen-(Ci-C6)-alkyl, Halogen-(Ci-C6)-alkoxy-halogen-(Ci-C6)-alkyl, Halogen-(C3-C7)-cycloalkoxy-(Ci-C6)-alkyl, (C3-C7)-Cycloalkenyloxy-(Ci-C6)-alkyl, Halogen-(C3-C7)-cycloalkenyloxy-(Ci-C6)-alkyl, Di-(Ci-C6)-alkoxy-(Ci-C6)-alkyl, (Ci-C6)- AI koxy-(Ci-C6)-al kyl-carbonyl, (Ci-C6)-Alkoxy-carbonyl-(Ci-C6)-alkyl, Halogen-(Ci-C6)- al koxy-carbonyl, (Ci-Cio)-Alkoxy, Halogen-(Ci-Cio)-alkoxy, (C3-Ci2)-Cycloalkoxy, Halogen-(C3-C7)-cycloalkoxy, (C3-C7)-Cycloalkyl-(Ci-C6)-alkoxy, (C2-Ci2)-Alkenyloxy, Halogen-(C2-Cio)-alkenyloxy, (C2-Cio)-Alkinyloxy, Halogen-(C3-Cio)-alkinyloxy, (C1-C6)- alkoxy-(Ci-C6)-alkoxy, (Ci-C6)-Alkyl-carbonyloxy, Halogen-(C2-Ci2)-alkyl-carbonyloxy, (C3-C7)-Cycloalkyl-carbonyloxy, (Ci-C6)-Alkyl-carbonyl-(Ci-C6)-alkoxy, (C1-C10)- Alkylthio, Halogen-(Ci-Cio)-alkylthio, (C3-Ci2)-Cycloalkylthio, (Ci-Cio)-Alkylsulfinyl, Halogen-(Ci-Cio)-alkylsulfinyl, (Ci-Cio)-alkylsulfonyl, Halogen-(Ci-Cio)-alkylsulfonyl, (C3-Ci2)-Cycloal kylsulfonyl , (Ci -C6)-Al kyl-carbonylth io, (Ci -C6)-Al kyl(th iocarbonyl )th io, (C3-Ci2)-Cycloalkylsulfinyl, (Ci-C6)-Alkylaminosulfonyl, Di-(Ci-C6)-alkylamino-sulfonyl, (Ci-C6)-Alkylamino, Di-(Ci-C6)-alkylamino, Halogen-(Ci-C6)-alkylamino, Halogen-di- (Ci-C6)-alkylamino, (C3-Ci2)-Cycloalkylamino, (Ci-C6)-Alkyl-carbonylamino, Halogen- (Ci-C6)-alkyl-carbonylamino, (Ci-Cio)-Alkylsulfonylamino, Halogen-(Ci-Cio)- alkylsulfonylamino, (C3-C7)-Cycloalkyl-(Ci-C6)-alkyl-amino, Cyano, Hydroxy, Amino, C(=O)OH, C(=O)NHOH, SO2NH2, SO2NHCN , SO2NHOH, NHCHO, G, W2G, W2OG, oder
Figure imgf000002_0001
wherein R 1 represents (C 1 -C 10) -alkyl, (C 2 -C 10) -alkenyl, (C 2 -C 10) -alkynyl, halogeno (C 1 -C 10) -alkyl, halogeno (C 2 -C 10) -alkenyl, halogen (C 2 -C 10) -alkynyl, (C 3 -C 10) -cycloalkyl, halogeno (C 3 -C 10) -cycloalkyl, (C 1 -C 6 ) -alkyl (C 3 -C 7 ) -cycloalkyl, ( C 3 -C 7 ) -cycloalkyl (C 1 -C 6 ) -alkyl, (C 3 -C 7 ) -cycloalkyl- (C 3 -C 7 ) -cycloalkyl, halogeno (C 3 -C 7 ) - cycloalkyl- (Ci-C 6) alkyl, (Ci-C 6) - alkyl (C 3 -C 7) cycloalkyl- (Ci-C 6) alkyl, (C3-Ci2) cycloalkenyl, halogen - (C 3 -C 2) - cycloalkenyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, (Ci-C6) alkoxy (C2-C6) alkenyl, (Ci-C 6 ) - Al kyl- (C 3 -C 7 ) -cycloal kyl, (Ci -C 6 ) -Al koxy- (C 3 -C 7 ) -cycloal kyl, (C 3 -C 7 ) -Cycloal koxy- (Ci - C 6) -alkyl, (C 3 -C 7) -Cycloal alkoxy- (Ci-C6) -al alkoxy- (Ci-C6) -alkyl, (Ci-C6) alkoxy- -Al ( Ci-C6) - alkoxy- (Ci-C 6) alkyl, (Ci-C6) alkylthio (Ci-C 6) alkyl, (Ci-C6) alkylsulfinyl (Ci-C 6) alkyl , (C 1 -C 6 ) -alkylsulfonyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylamino- (C 1 -C 6 ) -alkyl, di- (C 1 -C 6 ) -alkylamino- (C 1 -C 6 ) -alkyl ) -alkyl, halo (C 1 -C 6 ) -alkylamino (C 1 -C 6 ) -alkyl, (C 3 -C 7 ) -cycloalkylamino (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylcarbonyl, Halogeno (C 1 -C 6 ) -alkyl-carbonyl, (C 3 -C 7 ) -cycloalkylcarbonyl, (C 1 -C 4 ) -alkoxy-carbonyl, (C 3 -C 7 ) -cycloalkoxy-carbonyl, ( C 3 -C 7 ) -cycloalkyl- (C 1 -C 6 ) -alkoxycarbonyl, (C 1 -C 6 ) -alkylamino-carbonyl, di- (C 1 -C 6 ) -alkylaminocarbonyl, (C 3 -C 7 ) -cycloalkylamino carbonyl, cyano- (C 1 -C 6 ) -alkyl, hydroxy- (C 1 -C 6 ) -alkyl, (C 3 -C 7 ) -cycloalkenyl- (C 1 -C 6 ) -alkyl, halogen- (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy-halogeno (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkoxy-halogeno (C 1 -C 6 ) -alkyl, Halogeno (C 3 -C 7 ) -cycloalkoxy- (C 1 -C 6 ) -alkyl, (C 3 -C 7 ) -cycloalkenyloxy- (C 1 -C 6 ) -alkyl, halogeno (C 3 -C 7 ) -cycloalkenyloxy- (C 1 -C 6 ) -alkyl, di- (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy (C 1 -C 6 ) -alkylcarbonyl, (Ci-C6) alkoxy-carbonyl- (Ci-C 6) alkyl, halo (Ci-C 6) - al koxy-carbonyl, (Ci-Cio) alkoxy, halo (Ci-Cio) alkoxy , (C 3 -C 12) -cycloalkoxy, halo (C 3 -C 7 ) -cycloalkoxy, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 6 ) -alkoxy, (C 2 -C 12) -alkenyloxy, halogeno (C 2 -C 10) -alkenyloxy, (C 2 -C 10) -alkynyloxy, halogeno (C 3 -C 10) -alkynyloxy, (C 1 -C 6) -alkoxy- (C 1 -C 6) -alkoxy, (C 1 -C 6) -alkyl-carbonyloxy, halogeno (C 2 -C 12) -alkyl-carbonyloxy, (C 3 -C 7 ) -cycloalkyl-carbonyloxy, (C 1 -C 6 ) -alkyl-carbonyl- (C 1 -C 6 ) -alkoxy, (C 1 -C 10) -alkylthio, halogeno (C 1 -C 10) -alkylthio, (C 3 - Ci 2 ) -cycloalkylthio, (Ci-Cio) -alkylsulfinyl, halogeno (Ci-Cio) -alkylsulfinyl, (Ci-Cio) -alkylsulfonyl, halo (Ci-Cio) -alkylsulfonyl, (C 3 -Ci 2 ) - Cycloalkylsulfonyl, (C 1 -C 6 ) -alkylcarbonylthio, (C 1 -C 6 ) -alkyl (thiocarbonyl) thio, (C 3 -C 12) -cycloalkylsulfinyl, (C 1 -C 6 ) -alkylaminosulfonyl, di - (C 1 -C 6) -alkylamino-sulfonyl, (C 1 -C 6) -alkylamino, di- (C 1 -C 6) -alkylamino, halogeno (C 1 -C 6) -alkylamino, halo-di- (C 1 -C 6) -alkylamino , (C 3 -C 12) -cycloalkylamino, (C 1 -C 6) -alkylcarbonylamino, halogeno (C 1 -C 6) -alkylcarbonylamino, (C 1 -C 10 -alkyl) sulfonylamino, halogeno (C 1 -C 10) -alkylsulfonylamino, (C 3 -C 7 ) cyclo alkyl (C 1 -C 6) -alkylamino, cyano, hydroxy, amino, C (OO) OH, C (OO) NHOH, SO 2 NH 2, SO 2 NHCN, SO 2 NHOH, NHCHO, G, W 2 G, W 2 OG, or
R1 bedeutet Phenyl, Phenylsulfonyl, W1-(Phenyl), W1-(O-Phenyl), W1-(S-Phenyl), W1-(SO2-Phenyl), W2-(SO2CH2-Phenyl) oder W2-(SCH2-Phenyl), wobei die Phenylringe der acht vorstehend genannten Reste jeweils s Substituenten R6 tragen, R 1 is phenyl, phenylsulfonyl, W 1 - (phenyl), W 1 - (O-phenyl), W 1 - (S-phenyl), W 1 - (SO 2 -phenyl), W 2 - (SO 2 CH 2 Phenyl) or W 2 - (SCH 2 -phenyl), where the phenyl rings of the eight abovementioned radicals each carry s substituents R 6 ,
X1 bedeutet N oder CR2a, X2 bedeutet N oder CR2b, R2a bedeutet Phenyl oder W3-(Phenyl), wobei die Phenylringe der zwei vorstehend genannten Reste jeweils s Substituenten R6 tragen, oder X 1 is N or CR 2a , X 2 is N or CR 2b , R 2a is phenyl or W 3 - (phenyl), wherein the phenyl rings of the two radicals mentioned above each carry s substituents R 6 , or
R2a bedeutet G, W4G, Wasserstoff, Cyano, Amino, Nitro, CHO, C(=O)OH, R 2a represents G, W 4 G, is hydrogen, cyano, amino, nitro, CHO, C (= O) OH,
C(=O)NH2, C(=S)NH2, C(=O)NHCN, C(=O)NHOH, SH, SO2NH2, SO2NHCN, C (= O) NH 2 , C (= S) NH 2 , C (= O) NHCN, C (= O) NHOH, SH, SO 2 NH 2 , SO 2 NHCN,
SO2NHOH, SF5, NHCHO, NHNH2, NHOH, NHCN, NHC(O)NH2, (Ci-Cio)-Alkyl, (C2- Cio)-Alkenyl, (C2-Cio)-Alkinyl, Halogen-(Ci-Cio)-alkyl, Halogen-(C2-Cio)-alkenyl,SO 2 NHOH, SF 5, NHCHO, NHNH 2, NHOH, NHCN, NHC (O) NH2, (Ci-Cio) alkyl, (C 2 - Cio) alkenyl, (C2 -Cio) alkynyl, halogen (C 1 -C 10) -alkyl, halogeno (C 2 -C 10) -alkenyl,
Halogen-(C2-Cio)-alkinyl, (C3-C8)-Cycloalkyl, Halogen-(C3-C8)-cycloalkyl, (Ci-Ce)-Alkyl- (C3-C7)-cycloal kyl , (C3-C7)-Cycloal kyl-(Ci -C6)-al kyl , (Ci -C6)-Cycloal kyl-(Ci -C6)- cycloalkyl, Halogen-(Ci-C6)-Cycloalkyl-(Ci-C6)-alkyl, (Ci-C6)-Alkyl-(C3-C7)-cycloalkyl- (Ci-C6)-alkyl, (C3-C8)-Cycloalkenyl, Halogen-(C3-C8)-Cycloalkenyl, (Ci-Ce)-Alkoxy (Ci- C6)-alkyl, (C1 -C6)-Alkoxy (Ci-C6)-alkenyl, (Ci-C6)-Alkyl-(C3-C7)-cycloalkyl, (Ci-C6)- Al koxy-(C3-C7)-cycloal kyl , (Ci -C6)-Cycloal koxy-(Ci -C6)-al kyl , (C3-C7)-Cycloal koxy-(Ci - C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxy-(Ci-C6)-alkyl, (C2-C8)-Al ky Ith ioal ky I , (Ci-C6)- Alkylsulfinyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylsulfonyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylamino-(Ci- C6)-alkyl, Di-(Ci-C6)-alkylamino-(Ci-C6)-alkyl, Halogen-(Ci-C6)-alkylamino-(Ci-C6)- alkyl, (C3-C7)-Cycloalkylamino-(Ci-C6)-alkyl, (Ci-C6)-Alkyl-carbonyl, Halogen-(Ci-Ce)- alkyl-carbonyl, (C3-C7)-Cycloalkyl-carbonyl, (Ci-C6)-Alkoxy-carbonyl, (C3-C7)- Cycloalkoxy-carbonyl, (C3-C7)-Cycloalkyl-(Ci-C6)-alkoxy-carbonyl, (Ci-C6)-Alkylamino- carbonyl, Di-(Ci-C6)-alkyl-amino-carbonyl, (C3-C7)-Cycloalkyl-amino-carbonyl, Cyano- (Ci-C6)-alkyl, Hydroxy-(Ci-C6)-alkyl, (C3-C7)-Cycloalkenyl-(Ci-C6)-alkyl, Halogen-(Ci- C6)-alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-halogen-alkyl, Halogen-(Ci-Ce)- alkoxy-(Ci-C6)-halogen-alkyl, Halogen-(C3-C7)-cycloalkoxy-(Ci-C6)-alkyl, (C3-C7)- Cycloalkenyloxy-(Ci-C6)-alkyl, Halogen-(C3-C7)-cycloalkenyloxy-(Ci-C6)-alkyl, Di-(Ci- C6)-alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl-carbonyl, (Ci-C6)-Alkoxy- carbonyl-(Ci-C6)-alkyl, Halogen-(Ci-C6)-alkoxy-carbonyl, (Ci-C6)-Alkoxy, Halogen-(Ci- C6)-alkoxy, (C3-C8)-Cycloalkoxy, Halogen-(C3-C8)-cycloalkoxy, (C3-C7)-Cycloalkyl-(Ci- C6)-alkoxy, (C2-C6)-Alkenyloxy, Halogen-(C2-C6)-alkenyloxy, (C2-C6)-Alkinyloxy, Halogen-(C3-C6)-alkinyloxy, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxy, (Ci-C8)-Alkyl-carbonyloxy, Halogen-(Ci-C8)-alkylcarbonyloxy, (C3-C7)-Cycloalkyl-carbonyloxy, (Ci-Ce)-Alky- carbonyl-(Ci-C6)-alkoxy, (Ci-C6)-Alkylthio, Halogen-(Ci-C6)-alkylthio, (C3-C8)-Halo (C 2 -C 10) -alkynyl, (C 3 -C 8 ) -cycloalkyl, halo (C 3 -C 8 ) -cycloalkyl, (C 1 -C 6 ) -alkyl (C 3 -C 7 ) -cycloal kyl, (C 3 -C 7 ) -cycloalkyl (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -cycloalkyl (C 1 -C 6 ) -cycloalkyl, halogeno (C 1 -C 6 ) - cycloalkyl- (Ci-C 6) alkyl, (Ci-C 6) -alkyl- (C 3 -C 7) cycloalkyl- (Ci-C 6) alkyl, (C 3 -C 8) cycloalkenyl, halogen (C 3 -C 8 ) -cycloalkenyl, (C 1 -C 6 ) -alkoxy (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy (C 1 -C 6 ) -alkenyl, (C 1 -C 6 ) Alkyl (C 3 -C 7 ) -cycloalkyl, (C 1 -C 6 ) -alkoxy (C 3 -C 7 ) -cycloalkyl, (C 1 -C 6 ) -cycloalkoxy (C 1 -C 6 ) -alkyl, (C 3 -C 7 ) -cycloalkoxy (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, ( C 2 -C 8) -alkyl ky Ith ioal ky I, (Ci-C 6) - alkylsulfinyl (Ci-C6) alkyl, (Ci-C6) alkylsulfonyl (Ci-C 6) alkyl, (C -C 6) alkylamino (Ci- C6) alkyl, di (Ci-C6) alkylamino (Ci-C6) alkyl, halo (Ci-C6) alkylamino (Ci-C 6 ) - alkyl, (C 3 -C 7 ) -cycloalkylamino- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylcarbonyl, halogeno (C 1 -C 6 ) -alkylcarbo nyl, (C 3 -C 7) -cycloalkyl-carbonyl, (Ci-C6) alkoxy-carbonyl, (C 3 -C 7) - cycloalkoxy-carbonyl, (C 3 -C 7) cycloalkyl (Ci-C6 ) -alkoxycarbonyl, (C 1 -C 6 ) -alkylaminocarbonyl, di (C 1 -C 6 ) -alkyl-amino-carbonyl, (C 3 -C 7 ) -cycloalkyl-amino-carbonyl, cyano- (C 1 -C 4 -alkyl) 6 ) -alkyl, hydroxy (Ci-C 6 ) -alkyl, (C 3 -C 7 ) -cycloalkenyl- (Ci-C 6 ) -alkyl, halo (Ci- C 6 ) -alkoxy- (Ci-C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -haloalkyl, halogeno (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -haloalkyl, halogeno (C 3 -C 7 ) -cycloalkoxy- (C 1 -C 6 ) -alkyl, (C 3 -C 7 ) -cycloalkenyloxy- (C 1 -C 6 ) -alkyl, halogeno (C 3 -C 7 ) -cycloalkenyloxy- (C 1 -C 6 ) -alkyl , Di- (C 1 -C 6 ) alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl-carbonyl, (C 1 -C 6 ) -alkoxycarbonyl- ( C 1 -C 6) -alkyl, halogeno (C 1 -C 6) -alkoxycarbonyl, (C 1 -C 6) -alkoxy, halogeno (C 1 -C 4) -alkoxy, C6) -alkoxy, (C3-C8) -cycloalkoxy, halo (C3-C8) -cycloalkoxy, (C3-C7) -cycloalkyl- (Ci- C6) -alkoxy, (C2-C6) -alkenyloxy, halogen- C 2 -C 6) -alkenyloxy, (C 2 -C 6) -alkynyloxy, halogeno (C 3 -C 6) -alkynyloxy, (C 1 -C 6) -alkoxy- (C 1 -C 6) -alkoxy, (C 1 -C 8) -alkyl-carbonyloxy , Halogen- (C 1 -C 8) -alkylcarbonyloxy, (C 3 -C 7) -cycloalkyl-carbonyloxy, (C 1 -C 6 ) -alkylcarbonyl- (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkylthio, halogen - (Ci-C 6) -alkylthio, (C 3 -C 8) -
Cycloalkylthio, (Ci-C6)-Alkylsulfinyl, Halogen-(Ci-C6)-alkylsulfinyl, (Ci-C6)-Alkylsulfonyl, Halogen-(Ci-C6)-alkylsulfonyl, (C3-Cio)-Cycloalkylsulfonyl, (Ci-C6)-Alkylcarbonylthio, (Ci-C6)-Alkyl(thiocarbonyl)thio, (C3-C8)-Cycloalkylsulfinyl, (Ci-C6)-Alkylaminosulfonyl, Di-(Ci-C6)-alkylaminosulfonyl, (Ci-C6)-Alkylamino, Di-(Ci-C6)-alkylamino, Halogen-(Ci- C6)-alkylamino, Halogen-di-(Ci-C6)-alkylamino, (C3-C8)-Cycloalkylamino, (C2-C8)-Cycloalkylthio, (Ci-C6) alkylsulfinyl, halo (Ci-C6) alkylsulfinyl, (Ci-C 6) alkylsulfonyl, halo (Ci-C6) alkylsulfonyl, (C3-Cio) cycloalkylsulfonyl, ( C 1 -C 6) -alkylcarbonylthio, (C 1 -C 6) -alkyl (thiocarbonyl) thio, (C 3 -C 8) -cycloalkylsulfinyl, (C 1 -C 6) -alkylaminosulfonyl, di- (C 1 -C 6) -alkylaminosulfonyl, (C 1 -C 6) Alkylamino, di- (Ci-C6) -alkylamino, halo (Ci- C6) -alkylamino, halo-di- (Ci-C6) -alkylamino, (C3-C8) -cycloalkylamino, (C2-C8) -
Alkylcarbonylamino, Halogen-(C2-C8)-alkylcarbonylamino, (Ci-Cio)-Alkylsulfonylamino, Halogen-(Ci-Cio)-alkylsulfonylamino, (C3-C7)-Cycloalkyl-(Ci-C6)-alkyl-amino oder Halogen-tri-(Ci-C4)-alkylsilyl, R2b bedeutet Wasserstoff, Halogen, Cyano, Nitro, (Ci-C )-Alkyl, (Ci-C )-Haloalkyl, (C2-C6)-Alkenyl, (C2-C6)-Halogenalkenyl, (C2-C6)-Alkinyl, (C2-C6)-Halogenalkinyl, (C3- C6)-Cycloalkyl, (C3-C6)-Halogencycloalkyl, (Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, (C3-C6)- Cycloalkyl-(Ci-C6)-alkyl, (Ci-C )-Alkoxy oder (Ci-C )-Haloalkoxy, 1, Q2, Q3 oder Q4, Alkylcarbonylamino, halo (C 2 -C 8) -alkylcarbonylamino, (C 1 -C 10) -alkylsulfonylamino, halogeno (C 1 -C 10) -alkylsulfonylamino, (C 3 -C 7) -cycloalkyl- (C 1 -C 6) -alkylamino or halogeno tri (C 1 -C 4 ) -alkylsilyl, R 2b is hydrogen, halogen, cyano, nitro, (C 1 -C 4) -alkyl, (C 1 -C 4) -haloalkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 4 ) -alkylbenzyl, C 6) haloalkenyl, (C2-C6) -alkynyl, (C2-C6) -haloalkynyl, (C 3 - C 6) cycloalkyl, (C3-C 6) halocycloalkyl, (Ci-C6) alkyl -O- (Ci-C 6) alkyl, (C 3 -C 6) - cycloalkyl, (Ci-C 6) alkyl, (Ci-C) alkoxy or (Ci-C) haloalkoxy, 1, Q 2 , Q 3 or Q 4 ,
Figure imgf000005_0001
Figure imgf000005_0001
R3 bedeutet (Ci-C8)-Alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, wobei diese Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Cyano, Hydroxy, Nitro, SiR10 3, PO(OR10)2, S(O)n-(Ci-C6)-Alkyl, (Ci-C6)-Alkoxy, Halogen-(Ci-C6)-alkoxy,R 3 is (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, where these radicals are each represented by s radicals from the group consisting of halogen, cyano, hydroxyl, Nitro, SiR 10 3 , PO (OR 10 ) 2 , S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy,
COR3a, COOR3a, OCOR3a, NR3aCOR3a, NR3aSO2R3b, (C3-C6)-Cycloalkyl, Heteroaryl, Heterocyclyl oder Phenyl substituiert sind, wobei die 4 letztgenannten Reste jeweils durch p Reste aus der Gruppe bestehend aus Methyl, Ethyl, Methoxy, Trifluormethyl, Cyano und Halogen substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, oder R3 bedeutet Phenyl, das durch p Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, S(O)n-(Ci-C6)- Alkyl, (Ci-Ce)-Alkoxy, Halogen-(Ci-C6)-alkoxy und (Ci-C6)-Alkoxy-(Ci-C )-alkyl substituiert ist, COR 3a , COOR 3a , OCOR 3a , NR 3a COR 3a , NR 3a SO 2 R 3b , (C 3 -C 6 ) -cycloalkyl, heteroaryl, heterocyclyl or phenyl are substituted, wherein the 4 latter radicals each by p radicals from the Group consisting of methyl, ethyl, methoxy, trifluoromethyl, cyano and halogen are substituted, and wherein heterocyclyl n carries oxo groups, or R 3 is phenyl which is represented by p radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy and (C 1 -C 6 ) -alkoxy- (C 1 -C 4) -alkyl is
R3a bedeutet Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (C3-C6)- Cycloalkyl oder (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl oder Phenyl, R 3a is hydrogen, (Ci-C 6) -alkyl, (C2-C6) alkenyl, (C2-C6) -alkynyl, (C 3 -C 6) - cycloalkyl or (C3-C6) cycloalkyl (C 1 -C 6) -alkyl or phenyl,
R3b bedeutet (Ci-C6)-Alkyl, (C2-C6)-Alkenyl oder (C2-C6)-Alkinyl, (C3-C6)-Cycloalkyl oder (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl oder Phenyl, R 3b represents (Ci-C 6) -alkyl, (C 2 -C 6) -alkenyl or (C2-C6) -alkynyl, (C3-C6) -cycloalkyl or (C3-C6) cycloalkyl (Ci -C 6 ) -alkyl or phenyl,
R4 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (C3-C7)-cyclo-Alkyl, Halogen-(Ci-C6)-alkyl, (Ci-Ce)-Alkoxy, Halogen-(Ci-C6)-alkoxy, (C2-C6)-Alkenyl, (C2-C6)-Alkenyloxy, (C2-C6)- Halogenalkenyl, (C2-C6)-Alkinyl, (C2-C6)-Alkinyloxy, (C2-C6)-Halogenalkinyl, (Ci-C6)- Alkoxy-(Ci-C6)-Alkyl, Cyano, Nitro, Methylsulfenyl, Methylsulfinyl, Methylsulfonyl, Acetylamino, Benzoylamino, Methoxycarbonyl, Ethoxycarbonyl, R 4 represents hydrogen, (Ci-C 6) -alkyl, (C 3 -C 7) -cycloalkyl, halo (Ci-C 6) alkyl, (Ci-Ce) alkoxy, halo (Ci- C 6) alkoxy, (C2-C6) alkenyl, (C2-C6) alkenyloxy, (C 2 -C 6) - haloalkenyl, (C2-C6) -alkynyl, (C2-C6) - alkynyloxy, (C2-C6) haloalkynyl, (Ci-C6) - alkoxy- (Ci-C6) alkyl, cyano, nitro, methylsulphenyl, methylsulphinyl, methylsulphonyl, acetylamino, benzoylamino, methoxycarbonyl, ethoxycarbonyl,
Methoxycarbonylmethyl, Ethoxycarbonylmethyl, Benzoyl, Methylcarbonyl, Methoxycarbonylmethyl, ethoxycarbonylmethyl, benzoyl, methylcarbonyl,
Piperidinylcarbonyl, Trifluormethylcarbonyl, Halogen, Amino, Aminocarbonyl, Piperidinylcarbonyl, trifluoromethylcarbonyl, halogen, amino, aminocarbonyl,
Methylaminocarbonyl, Dimethylaminocarbonyl, Methoxymethyl, oder Methylaminocarbonyl, dimethylaminocarbonyl, methoxymethyl, or
jeweils durch p Reste aus der Gruppe bestehend aus Methyl, Ethyl, Methoxy, in each case by p radicals from the group consisting of methyl, ethyl, methoxy,
Trifluormethyl und Halogen substituiertes Heteroaryl, Heterocyclyl oder Phenyl, Trifluoromethyl and halogen substituted heteroaryl, heterocyclyl or phenyl,
R5 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-Alkyl, CH2R5a, (C3- C7)-Cycloalkyl, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-alkenyl, (C2- Ce)-Alkinyl, Halogen-(C2-C6)-alkinyl, OR6, NHR6, Methoxycarbonyl, Ethoxycarbonyl, Methoxycarbonylmethyl, Ethoxycarbonylmethyl, Methylcarbonyl, R 5 represents hydrogen, (Ci-C 6) -alkyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, CH 2 R 5a, (C 3 - C 7) cycloalkyl, halo ( Ci-C 6) alkyl, (C2-C6) alkenyl, halo (C2-C6) alkenyl, (C2 - Ce) alkynyl, halo (C2-C6) alkynyl, OR 6, NHR 6 , methoxycarbonyl, ethoxycarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, methylcarbonyl,
Trifluormethylcarbonyl, Dimethylamino, Acetylamino, Methylsulfenyl, Methylsulfinyl, Methylsulfonyl oder jeweils durch p Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, S(O)n-(Ci-C6)- Alkyl, (Ci-Ce)-Alkoxy, Halogen-(Ci-C6)-alkoxy, (Ci-C6)-Alkoxy-(Ci-C )-alkyl Trifluoromethylcarbonyl, dimethylamino, acetylamino, methylsulfenyl, methylsulfinyl, methylsulfonyl or in each case by p radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 3 -C 4 ) -alkyl C 6 ) -cycloalkyl, S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkoxy- Ci-C) -alkyl
substituiertes Heteroaryl, Heterocyclyl, Benzyl oder Phenyl, substituted heteroaryl, heterocyclyl, benzyl or phenyl,
R5a bedeutet Acetoxy, Acetamido, N-Methylacetamido, Benzoyloxy, Benzamido, N- Methylbenzamido, Methoxycarbonyl, Ethoxycarbonyl, Benzoyl, Methylcarbonyl, Piperidinylcarbonyl, Morpholinylcarbonyl, Trifluormethylcarbonyl, Aminocarbonyl, Methylaminocarbonyl, Dimethylanninocarbonyl, (Ci-C6)-Alkoxy, (C3-C6)-Cycloalkyl oder jeweils durch p Reste aus der Gruppe bestehend aus Methyl, Ethyl, Methoxy, R 5a represents acetoxy, acetamido, N-methylacetamido, benzoyloxy, benzamido, N-methylbenzamido, methoxycarbonyl, ethoxycarbonyl, benzoyl, methylcarbonyl, Piperidinylcarbonyl, morpholinylcarbonyl, trifluoromethylcarbonyl, aminocarbonyl, methylaminocarbonyl, dimethylanninocarbonyl, (C 1 -C 6) -alkoxy, (C 3 -C 6) -cycloalkyl or in each case by p radicals from the group consisting of methyl, ethyl, methoxy,
Trifluormethyl und Halogen substituiertes Heteroaryl oder Heterocyclyl, Trifluoromethyl and halogen substituted heteroaryl or heterocyclyl,
Y bedeutet O oder S, Y is O or S,
W1 bedeutet (Ci-Cio)-Alkylen, (C2-C6)-Alkenylen oder (C2-C6)-Alkinylen, W2, W3 und W4 bedeuten jeweils (Ci-Cio)-Alkylen, W 1 represents (Ci-Cio) alkylene, (C 2 -C 6) -alkenylene or (C2-C6) alkynylene, W 2, W 3 and W 4 each represents (Ci-Cio) alkylene,
G bedeutet jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-C6)-Alkoxy, Halogen-(Ci-C6)-alkoxy und (Ci-C6)-Alkoxy-(Ci-C4)-alkyl substituiertes Heteroaryl oder Heterocyclyl, wobei Heterocyclyl n Oxogruppen trägt, G means each consisting of halogen, nitro, cyano substituted by s radicals selected from the group (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C3-C6) -cycloalkyl, S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy and (C 1 -C 6 ) -alkoxy- (C 1 -C 4 ) -alkyl-substituted heteroaryl or heterocyclyl, where heterocyclyl carries n oxo groups,
R6 bedeutet Halogen, Cyano, Hydroxy, Amino, Nitro, -CHO, -C(=O)OH, R 6 is halogen, cyano, hydroxy, amino, nitro, -CHO, -C (= O) OH,
-C(=O)NH2, -C(=S)NH2, -C(=O)NHCN, -C(=O)NHOH, -SH, -SO2NH2, -SO2NHCN, -SO2NHOH, -OCN, -SCN, -SF5, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, -C (= O) NH 2 , -C (= S) NH 2 , -C (= O) NHCN, -C (= O) NHOH, -SH, -SO 2 NH 2 , -SO 2 NHCN, -SO 2 NHOH, -OCN, -SCN, -SF 5, (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl,
Halogen-(Ci-C6)-alkyl, Halogen-(C2-C6)-alkenyl, Halogen-(C2-C6)-alkinyl, (C3-C8)- Cycloalkyl, Halogen-(C3-C8)-cycloalkyl, (Ci-C6)-Alkyl-(C3-C7)-cycloalkyl, (C3-C7)- Cycloalkyl-(Ci-C6)-alkyl, (C3-C8)-Cycloalkenyl, Halogen-(C3-C8)-cycloalkenyl, (C1-C6)- Al koxy-(Ci -C6)-al kyl , (C3-C7)-Cycloal koxy-(Ci -C6)-al kyl , (Ci -C6)-Al koxy-(Ci -C6)-al koxy- (Ci-C6)-alkyl, (Ci -C6)-Al kylth io-(Ci -C6)-al kyl , (Ci-C8)-Alkylsulfinyl-(Ci-C6)-alkyl, (Ci-C8)- Alkoxy-halogen-(Ci-C6)-alkyl, Cyano-(Ci-C6)-alkyl, Hydroxy-(Ci-C6)-alkyl, (Ci-C6)- Alkoxy, Halogen-(Ci-C6)-alkoxy, (C3-C8)-Cycloalkoxy, Halogen-(C3-C8)-cycloalkoxy, (C3-C8)-Cycloalkyl-(Ci-C6)-alkoxy, (C2-C6)-Alkenyloxy, Halogen-(C2-C6)-alkenyloxy, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxy, (C2-C6)-Alkylcarbonyloxy, (Ci-C6)-Alkylthio, Halogen- (Ci-C6)-alkylthio, (C3-C8)-Cycloal kylth io, (Ci-C6)-Alkylsulfinyl, Halogen-(Ci-C6)- alkylsulfinyl, (Ci-C6)-Alkylsulfonyl, Halogen-(Ci-C6)-alkylsulfonyl, (C3-C8)-Halo (Ci-C 6) alkyl, halo (C 2 -C 6) alkenyl, halo (C 2 -C 6) -alkynyl, (C 3 -C 8) - cycloalkyl, halo (C 3 -C 8) cycloalkyl, (Ci-C6) alkyl- (C 3 -C 7) cycloalkyl, (C 3 -C 7) - cycloalkyl- (Ci-C6) alkyl, (C 3 -C 8) - cycloalkenyl, halo (C 3 -C 8) -cycloalkenyl, (C1-C6) - Al alkoxy- (Ci-C6) -alkyl, (C 3 -C 7) -Cycloal alkoxy- (Ci-C6) - al kyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) - al kyl, (C 1 -C 8 ) -alkylsulfinyl- (C 1 -C 6 ) -alkyl, (C 1 -C 8 ) -alkoxy-halo (C 1 -C 6 ) -alkyl, cyano- (C 1 -C 6 ) - alkyl, hydroxy (Ci-C 6) alkyl, (Ci-C 6) - alkoxy, halo (Ci-C6) alkoxy, (C 3 -C 8) cycloalkoxy, halo (C 3 -C 8 ) -cycloalkoxy, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -alkoxy, (C 2 -C 6) -alkenyloxy, halogeno (C 2 -C 6) -alkenyloxy, (C 1 -C 6) -alkoxy-) (Ci-C 6) alkoxy, (C 2 -C 6) alkylcarbonyloxy, (Ci-C 6) alkylthio, halo (Ci-C 6) -alkylthio, (C 3 -C 8) -Cycloal kylth io , (C 1 -C 6 ) -alkylsulfinyl, halogeno (C 1 -C 6 ) -alkylsulfinyl, (C 1 -C 6 ) -alkylsulfone onyl, halo (C 1 -C 6 ) -alkylsulfonyl, (C 3 -C 8 ) -
Cycloalkylsulfonyl, (Ci-C6)-Alkylamino, Di-(Ci-C6)-alkylamino, Halogen-(Ci-C6)- alkylamino, Halogen-di-(Ci-C8)-alkylamino oder (C3-C8)-Cycloalkylamino, oder zwei vicinale Reste R6 bilden eine (C3-C6)-Alkylengruppe, in der p Kohlenstoffatome durch Sauerstoff, Schwefel oder Stickstoff ersetzt sind, und in der ein Kohlenstoffatom t Oxogruppen trägt, n bedeutet 0, 1 oder 2, p bedeutet 0, 1 , 2 oder 3, s bedeutet 0, 1 , 2, 3, 4 oder 5, t bedeutet 0 oder 1 . Cycloalkylsulfonyl, (Ci-C6) alkylamino, di- (Ci-C6) alkylamino, halo (Ci-C6) - alkylamino, halogen-di- (Ci-C 8) alkylamino or (C 3 -C 8) Cycloalkylamino, or two vicinal radicals R 6 form a (C 3 -C 6) -alkylene group in which p is carbon atoms Oxygen, sulfur or nitrogen are substituted, and in which a carbon atom t carries oxo groups, n means 0, 1 or 2, p means 0, 1, 2 or 3, s means 0, 1, 2, 3, 4 or 5, t means 0 or 1.
In der Formel (I) und allen nachfolgenden Formeln können Alkylreste mit mehr als zwei Kohlenstoffatomen geradkettig oder verzweigt sein. Alkylreste bedeuten z.B. Methyl, Ethyl, n- oder i-Propyl, n-, i-, t- oder 2-Butyl, Pentyle, Hexyle, wie n-Hexyl, i-Hexyl und 1 ,3-Dimethylbutyl. Analog bedeutet AI kenyl z.B. Allyl, 1 -Methylprop-2-en-1 -yl, In formula (I) and all subsequent formulas, alkyl radicals having more than two carbon atoms may be straight-chain or branched. Alkyl radicals mean e.g. Methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i-hexyl and 1, 3-dimethylbutyl. Analogously, AI means kenyl, e.g. Allyl, 1-methylprop-2-en-1-yl,
2-Methyl-prop-2-en-1 -yl, But-2-en-1 -yl, But-3-en-1 -yl, 1 -Methyl-but-3-en-1 -yl und 1 -Methyl-but-2-en-1 -yl. Alkinyl bedeutet z.B. Propargyl, But-2-in-1 -yl, But-3-in-1 -yl, 1 -Methyl-but-3-in-1 -yl. Die Mehrfachbindung kann sich jeweils in beliebiger Position des ungesättigten Rests befinden. Cycloalkyl bedeutet ein carbocyclisches, gesättigtes Ringsystem mit drei bis sechs C-Atomen, z.B. Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl. Analog bedeutet Cycloalkenyl eine monocyclische Alkenylgruppe mit drei bis sechs Kohlenstoffringgliedern, z.B. Cyclopropenyl, Cyclobutenyl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methyl-but-3-en-1-yl and 1 - Methyl-but-2-en-1-yl. Alkynyl means e.g. Propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methyl-but-3-yn-1-yl. The multiple bond can each be in any position of the unsaturated radical. Cycloalkyl means a carbocyclic saturated ring system having three to six C atoms, e.g. Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. Similarly, cycloalkenyl is a monocyclic alkenyl group having three to six carbon ring members, e.g. Cyclopropenyl, cyclobutenyl,
Cyclopentenyl und Cyclohexenyl, wobei sich die Doppelbindung an beliebiger Position befinden kann. (Ci-Cio)-Alkylen bedeutet entsprechend eine Methylen-, Ethylen-, jeweils unverzweigte Propylen-, Butylen-, Pentylen-, Hexylen-, Heptylen-, Octylen-, Nonylen- oder Decylen-Gruppe. Cyclopentenyl and cyclohexenyl, wherein the double bond may be in any position. (C 1 -C 10) -alkylene accordingly denotes a methylene, ethylene, in each case unbranched propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene or decylene group.
Halogen steht für Fluor, Chlor, Brom oder lod. Halogen is fluorine, chlorine, bromine or iodine.
Heterocyclyl bedeutet einen gesättigten, teilgesättigten oder vollständig ungesättigten cyclischen Rest, der 3 bis 6 Ringatome enthält, von denen 1 bis 4 aus der Gruppe Sauerstoff, Stickstoff und Schwefel stammen, und der zusätzlich durch einen Benzoring annelliert sein kann. Beispielsweise steht Heterocyclyl für Piperidinyl, Pyrrolidinyl, Tetrahydrofuranyl, Dihydrofuranyl und Oxetanyl, Heterocyclyl means a saturated, partially saturated or fully unsaturated cyclic radical containing from 3 to 6 ring atoms, of which from 1 to 4 are from the group oxygen, nitrogen and sulfur, and additionally by a Benzoring can be annealed. For example, heterocyclyl is piperidinyl, pyrrolidinyl, tetrahydrofuranyl, dihydrofuranyl and oxetanyl,
Heteroaryl bedeutet einen aromatischen cyclischen Rest, der 3 bis 6 Ringatome enthält, von denen 1 bis 4 aus der Gruppe Sauerstoff, Stickstoff und Schwefel stammen, und der zusätzlich durch einen Benzolring annelliert sein kann. Heteroaryl means an aromatic cyclic radical containing from 3 to 6 ring atoms, of which from 1 to 4 are from the group consisting of oxygen, nitrogen and sulfur, and may additionally be fused by a benzene ring.
Beispielsweise steht Heteroaryl für Benzimidazol-2-yl, Furanyl, Imidazolyl, Isoxazolyl, Isothiazolyl, Oxazolyl, Pyrazinyl, Pyrimidinyl, Pyridazinyl, Pyridinyl, Benzisoxazolyl, Thiazolyl, Pyrrolyl, Pyrazolyl, Thiophenyl, 1 ,2,3-Oxadiazolyl, 1 ,2,4-Oxadiazolyl, 1 ,2,5- Oxadiazolyl, 1 ,3,4-Oxadiazolyl, 1 ,2,4-Triazolyl, 1 ,2,3-Triazolyl, 1 ,2,5-Triazolyl, 1 ,3,4- Triazolyl, 1 ,2,4-Triazolyl, 1 ,2,4-Thiadiazolyl, 1 ,3,4-Thiadiazolyl, 1 ,2,3-Thiadiazolyl, 1 ,2,5-Thiadiazolyl, 2H-1 ,2,3,4-Tetrazolyl, 1 H-1 ,2,3,4-Tetrazolyl, 1 ,2,3,4-Oxatriazolyl, 1 ,2,3,5-Oxatriazolyl, 1 ,2,3,4-Thiatriazolyl und 1 ,2,3,5-Thiatriazolyl. For example, heteroaryl is benzimidazol-2-yl, furanyl, imidazolyl, isoxazolyl, isothiazolyl, oxazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridinyl, benzisoxazolyl, thiazolyl, pyrrolyl, pyrazolyl, thiophenyl, 1, 2,3-oxadiazolyl, 1, 2 4-oxadiazolyl, 1, 2,5-oxadiazolyl, 1, 3,4-oxadiazolyl, 1, 2,4-triazolyl, 1, 2,3-triazolyl, 1, 2,5-triazolyl, 1, 3,4- Triazolyl, 1, 2,4-triazolyl, 1, 2,4-thiadiazolyl, 1, 3,4-thiadiazolyl, 1, 2,3-thiadiazolyl, 1, 2,5-thiadiazolyl, 2H-1,2,3, 4-tetrazolyl, 1 H-1, 2,3,4-tetrazolyl, 1, 2,3,4-oxatriazolyl, 1, 2,3,5-oxatriazolyl, 1, 2,3,4-thiatriazolyl and 1, 2 , 3,5-thiatriazolyl.
Ist eine Gruppe mehrfach durch Reste substituiert, so ist darunter zu verstehen, daß diese Gruppe durch ein oder mehrere gleiche oder verschiedene der genannten Reste substituiert ist. Analoges gilt für den Aufbau von Ringsystemen durch verschiedene Atome und Elemente. Dabei sollen solche Verbindungen vom Anspruchsbegehren ausgenommen sein, von denen der Fachmann weiß, dass sie unter If a group is repeatedly substituted by radicals, it is to be understood that this group is substituted by one or more identical or different radicals. The same applies to the construction of ring systems by different atoms and elements. In this case, such compounds should be excluded from the claim, which is known to the skilled person that under
Normalbedingungen chemisch instabil sind. Normal conditions are chemically unstable.
Die Verbindungen der allgemeinen Formel (I) können je nach Art und Verknüpfung der Substituenten als Stereoisomere vorliegen. Sind beispielsweise ein oder mehrere asymmetrische Kohlenstoffatome vorhanden, so können Enantiomere und Depending on the nature and linkage of the substituents, the compounds of the general formula (I) can exist as stereoisomers. For example, if one or more asymmetric carbon atoms are present, then enantiomers and
Diastereomere auftreten. Ebenso treten Stereoisomere auf, wenn n für 1 steht Diastereomers occur. Likewise, stereoisomers occur when n is 1
(Sulfoxide). Stereoisomere lassen sich aus den bei der Herstellung anfallenden(Sulfoxides). Stereoisomers can be obtained from the resulting in the preparation
Gemischen nach üblichen Trennmethoden, beispielsweise durch chromatographische Trennverfahren, erhalten. Ebenso können Stereoisomere durch Einsatz stereoselektiver Reaktionen unter Verwendung optisch aktiver Ausgangs- und/oder Mixtures according to customary separation methods, for example by chromatographic separation methods obtained. Likewise, stereoisomers can be prepared by using stereoselective reactions using optically active starting materials and / or
Hilfsstoffe selektiv hergestellt werden. Die Erfindung betrifft auch alle Stereoisomeren und deren Gemische, die von der allgemeinen Formel (I) umfasst, jedoch nicht spezifisch definiert sind. Die erfindungsgemäßen Verbindungen können auf Grund der Oximether-Struktur auch als geometrische Isomere (E-/Z-lsomere) auftreten. Die Erfindung betrifft auch alle E-/Z-lsomere und deren Gemische, die von der allgemeinen Formel (I) umfasst, jedoch nicht spezifisch definiert sind. Die Verbindungen der Formel (I) können Salze bilden. Geeignete Basen sind beispielsweise organische Amine , wie Trialkylamine, Morpholin, Piperidin oder Pyridin sowie Ammonium-, Alkali- oder Erdalkalimetallhydroxide, -carbonate und -hydrogen- carbonate, insbesondere Natrium- und Kaliumhydroxid, Natrium- und Kaliumcarbonat und Natrium- und Kaliumhydrogencarbonat. Diese Salze sind Verbindungen, in denen der acide Wasserstoff durch ein für die Landwirtschaft geeignetes Kation ersetzt wird, beispielsweise Metallsalze, insbesondere Alkalimetallsalze oder Erdalkalimetallsalze, insbesondere Natrium- und Kaliumsalze, oder auch Ammoniumsalze, Salze mit organischen Aminen oder quartäre (quaternäre) Ammoniumsalze, zum Beispiel mit Kationen der Formel [NRR'R"R"']+, worin R bis R'" jeweils unabhängig voneinander einen organischen Rest, insbesondere Alkyl, Aryl, Aralkyl oder Alkylaryl darstellen. Infrage kommen auch Alkylsulfonium- und Alkylsulfoxoniumsalze, wie (Ci-C4)- Trialkylsulfonium- und (Ci-C4)-Trialkylsulfoxoniumsalze. Auxiliaries are selectively produced. The invention also relates to all stereoisomers and mixtures thereof which are of the general formula (I), but not specifically defined. The compounds of the invention may also occur as geometric isomers (E / Z isomers) due to the oxime ether structure. The invention also relates to all E / Z isomers and mixtures thereof, which are of the general formula (I), but not specifically defined. The compounds of formula (I) can form salts. Examples of suitable bases are organic amines, such as trialkylamines, morpholine, piperidine or pyridine, and also ammonium, alkali metal or alkaline earth metal hydroxides, carbonates and bicarbonates, in particular sodium and potassium hydroxide, sodium and potassium carbonate and sodium and potassium bicarbonate. These salts are compounds in which the acidic hydrogen is replaced by an agriculturally suitable cation, for example metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or else ammonium salts, salts with organic amines or quaternary ammonium salts Example with cations of the formula [NRR ' R ' R '' ] + , where R 1 to R '" each independently of one another represent an organic radical, in particular alkyl, aryl, aralkyl or alkylaryl.Suitable are also alkylsulfonium and alkylsulfoxonium salts, such as (Ci -C 4) - trialkylsulfonium and (Ci-C 4) -Trialkylsulfoxoniumsalze.
Die Verbindungen der Formel (I) können durch Anlagerung einer geeigneten The compounds of formula (I) can be prepared by addition of a suitable
anorganischen oder organischen Säure, wie beispielsweise Mineralsäuren, wie HCl, HBr, H2SO4, H3PO4 oder HNO3, oder organische Säuren, z. B. Carbonsäuren, wie Ameisensäure, Essigsäure, Propionsäure, Oxalsäure, Milchsäure oder Salicylsäure oder Sulfonsäuren, wie p-Toluolsulfonsäure, an eine basische Gruppe, wie Amino, Alkylamino, Dialkylamino, Piperidino, Morpholino oder Pyridino, Salze bilden. Diese Salze enthalten dann die konjugierte Base der Säure als Anion. inorganic or organic acid, such as mineral acids such as HCl, HBr, H 2 SO 4, H3PO 4 or HNO 3, or organic acids, eg. For example, carboxylic acids such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or sulfonic acids such as p-toluenesulfonic acid to form a basic group such as amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino, salts. These salts then contain the conjugate base of the acid as an anion.
Bevorzugt sind Verbindungen der allgemeinen Formel (I), worin Preference is given to compounds of the general formula (I) in which
R1 bedeutet (Ci-Cio)-Alkyl, (C2-Cio)-Alkenyl, (C2-Cio)-Alkinyl, Halogen-(Ci-Cio)- alkyl, Halogen-(C2-Cio)-alkenyl, Halogen-(C2-Cio)-alkinyl, (C3-Cio)-Cycloalkyl, Halogen- (C3-Cio)-cycloal kyl , (C1 -C )-Al kyl-(C3-C7)-cycloal kyl , (C3-C7)-Cycloal kyl- (Ci-C6)-alkyl, (C3-C7)-Cycloalkyl-(C3-C7)-cycloalkyl, Halogen-(C3-C7)-cycloalkyl- (C1 -C6)-al kyl , (C1 -C6)-Al kyl-(C3-C7)-cycloal kyl-(Ci -C6)-al kyl , (C3-Ci2)-Cycloal kenyl , Halogen-(C3-Ci2)-cycloalkenyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(C2-C6)- al kenyl, (Ci-C6)-Alkyl-(C3-C7)-cycloalkyl, (Ci-C6)-Alkoxy-(C3-C7)-cycloalkyl, (C3-C7)- Cycloal koxy-(Ci -C6)-al kyl , (C3-C7)-Cycloal koxy-(Ci -C6)-al koxy-(Ci -C6)-al kyl , (C1 -C6)- Al koxy-(Ci -C6)-al koxy-(Ci -C6)-al kyl , (C1 -C6)-Al kylth io-(Ci -C6)-al kyl , (C1 -C6)- Alkylsulfinyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylsulfonyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylamino- (Ci-C6)-alkyl, Di-(Ci-C6)-alkylamino-(Ci-C6)-alkyl, Halogen-(Ci-C6)-alkylamino- (Ci-C6)-alkyl, (C3-C7)-Cycloalkylamino-(Ci-C6)-alkyl, (Ci-C6)-Alkyl-carbonyl, Halogen- (Ci -C6)-al kyl-carbonyl , (C3-C7)-Cycloal kyl-carbonyl , (Ci -ΟΘ)-ΑΙ koxy-carbonyl , R 1 represents (C 1 -C 10) -alkyl, (C 2 -C 10) -alkenyl, (C 2 -C 10) -alkynyl, halogeno (C 1 -C 10) -alkyl, halogeno (C 2 -C 10) -alkenyl, halogen - (C 2 -C 10) -alkynyl, (C 3 -C 10) -cycloalkyl, halogeno (C 3 -C 10) -cycloalkyl, (C 1 -C 6 ) -alkyl (C 3 -C 7 ) -cycloalkyl, ( C 3 -C 7 ) -cycloalkyl (C 1 -C 6 ) -alkyl, (C 3 -C 7 ) -cycloalkyl- (C 3 -C 7 ) -cycloalkyl, halogeno (C 3 -C 7 ) -cycloalkyl - (C 1 -C 6 ) -alcyl, (C 1 -C 6 ) -alkyl (C 3 -C 7 ) -cycloalkyl (C 1 -C 6 ) -alkyl, (C 3 -C 2 ) - Cycloalkenyl, halogen- (C 3 -C 12) -cycloalkenyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 2 -C 6 ) -alkhenyl, (Ci-C6) alkyl- (C3-C7) cycloalkyl, (Ci-C 6) alkoxy (C3-C7) cycloalkyl, (C 3 -C 7) - cycloalkylene alkoxy- (Ci - C 6) -alkyl, (C 3 -C 7) -Cycloal alkoxy- (Ci-C6) -al alkoxy- (Ci-C6) -alkyl, (C1-C6) - Al alkoxy- (C -C6) -al alkoxy- (Ci-C6) -alkyl, (C1-C6) -alkyl kylth io- (Ci-C6) -alkyl, (C1-C6) - alkylsulfinyl (Ci C 6 ) -alkyl, (C 1 -C 6 ) -alkylsulfonyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylamino (C 1 -C 6 ) -alkyl, di- (C 1 -C 6 ) -alkylamino (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkylamino (C 1 -C 6 ) -alkyl, (C 3 -C 7) Cycloalkylamino- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylcarbonyl, halogeno (C 1 -C 6 ) -alkylcarbonyl, (C 3 -C 7) -cycloalkylcarbonyl, (C 1 -C 4 ) -cycloalkyl; ) -Koxy-carbonyl,
(C3-C7)-Cycloal koxy-carbonyl , (C3-C7)-Cycloal kyl-(Ci -C6)-al koxy-carbonyl , (Ci -Ce)- Alkylamino-carbonyl, Di-(Ci-C6)-alkylamino-carbonyl, (C3-C7)-Cycloalkylamino- carbonyl, Cyano-(Ci-C6)-alkyl, Hydroxy-(Ci-C6)-alkyl, (C3-C7)-Cycloalkenyl-(Ci-C6)- alkyl, Halogen-(Ci-C6)-alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-halogen-(Ci-C6)-alkyl, Halogen-(Ci-C6)-alkoxy-halogen-(Ci-C6)-alkyl, Halogen-(C3-C7)-cycloalkoxy-(Ci-C6)- alkyl, (C3-C7)-Cycloalkenyloxy-(Ci-C6)-alkyl, Halogen-(C3-C7)-cycloalkenyloxy- (Ci-C6)-alkyl, Di-(Ci-C6)-alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl-carbonyl, (Ci-C6)-Alkoxy-carbonyl-(Ci-C6)-alkyl, Halogen-(Ci-C6)-alkoxy-carbonyl, (C1-C10)- Alkoxy, Halogen-(Ci-Cio)-alkoxy, (C3-Ci2)-Cycloalkoxy, Halogen-(C3-C7)-cycloalkoxy, (C3-C7)-Cycloalkyl-(Ci-C6)-alkoxy, (C2-Ci2)-Alkenyloxy, Halogen-(C2-Cio)-alkenyloxy, (C2-Cio)-Alkinyloxy, Halogen-(C3-Cio)-alkinyloxy, (Ci-C6)-alkoxy-(Ci-C6)-alkoxy, (C1- C6)-Alkyl-carbonyloxy, Halogen-(C2-Ci2)-alkyl-carbonyloxy, (C3-C7)-Cycloalkyl- carbonyloxy, (Ci-C6)-Alkyl-carbonyl-(Ci-C6)-alkoxy, (Ci-Cio)-Al kylthio, Halogen-(Ci- Cio)-alkylthio, (C3-Ci2)-Cycloalkylthio, (Ci-Cio)-Alkylsulfinyl, Halogen-(Ci-Cio)- alkylsulfinyl, (Ci-Cio)-alkylsulfonyl, Halogen-(Ci-Cio)-alkylsulfonyl, (C3-C12)- Cycloalkylsulfonyl, (Ci-C6)-Alkyl-carbonylthio, (Ci-C6)-Alkyl(thiocarbonyl)thio, (C3-C12)- Cycloalkylsulfinyl, (Ci-C6)-Alkylaminosulfonyl, Di-(Ci-C6)-alkylamino-sulfonyl, (C1-C6)- Alkylamino, Di-(Ci-C6)-alkylamino, Halogen-(Ci-C6)-alkylamino, Halogen-di-(Ci-C6)- alkylamino, (C3-Ci2)-Cycloalkylamino, (Ci-C6)-Alkyl-carbonylamino, Halogen-(Ci-C6)- alkyl-carbonylamino, (Ci-Cio)-Alkylsulfonylamino, Halogen-(Ci-Cio)-alkylsulfonylamino, (C3-C7)-Cycloalkyl-(Ci-C6)-alkyl-amino, Cyano, Hydroxy, Amino, C(=O)OH, (C 3 -C 7) -cycloalkoxy-carbonyl, (C 3 -C 7) -cycloalkyl (C 1 -C 6) -alkoxycarbonyl, (C 1 -C 6) -alkylaminocarbonyl, di- (C 1 -C 6) -alkylamino carbonyl, (C 3 -C 7) -cycloalkylaminocarbonyl, cyano- (C 1 -C 6) -alkyl, hydroxy- (C 1 -C 6) -alkyl, (C 3 -C 7) -cycloalkenyl- (C 1 -C 6) -alkyl, halogen - (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy-halogeno (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkoxy-halogeno ( C 1 -C 6) -alkyl, halogeno (C 3 -C 7) -cycloalkoxy- (C 1 -C 6) -alkyl, (C 3 -C 7) -cycloalkenyloxy- (C 1 -C 6) -alkyl, halogeno (C 3 -C 7) -cycloalkenyloxy - (Ci-C 6 ) -alkyl, di- (Ci-C6) -alkoxy- (Ci-C 6 ) -alkyl, (Ci-C6) -alkoxy- (Ci-C 6 ) -alkyl-carbonyl, (Ci -C6) alkoxycarbonyl (Ci-C6) alkyl, halogeno (Ci-C6) -alkoxycarbonyl, (C1-C10) - alkoxy, halogeno (Ci-Cio) -alkoxy, (C3-Ci2 ) -Cycloalkoxy, halo (C3-C7) -cycloalkoxy, (C3-C7) -cycloalkyl- (Ci-C6) -alkoxy, (C2-Ci2) -alkenyloxy, halo (C2-Cio) -alkenyloxy, (C2 -C) alklyloxy, halo (C 3 -C 10) -alkynyloxy, (C 1 -C 6) -alkoxy- (C 1 -C 6) -alkoxy, (C 1 -C 6) -alkyl-carbonyloxy, halogeno (C 2 -C 12) alkyl-carbonyloxy, (C3-C7) -Cy cycloalkylcarbonyloxy, (C 1 -C 6) -alkylcarbonyl- (C 1 -C 6) -alkoxy, (C 1 -C 10) -alkylthio, halogeno (C 1 -C 10) -alkylthio, (C 3 -C 12) -cycloalkylthio, (C 1 -C 10) -alkylsulfinyl, halogeno (C 1 -C 10) -alkylsulfinyl, (C 1 -C 10) -alkylsulfonyl, halogeno (C 1 -C 10) -alkylsulfonyl, (C 3 -C 12) -cycloalkylsulfonyl, (C 1 -C 6 ) Alkylcarbonylthio, (C 1 -C 6 ) -alkyl (thiocarbonyl) thio, (C 3 -C 12) -cycloalkylsulfinyl, (C 1 -C 6 ) -alkylaminosulfonyl, di- (C 1 -C 6 ) -alkylaminosulfonyl, (C 1 -C 6 ) - alkylamino, di- (C 1 -C 6) -alkylamino, halogeno (C 1 -C 6) -alkylamino, halo-di- (C 1 -C 6) -alkylamino, (C 3 -C 12) -cycloalkylamino, (C 1 -C 6) - Alkylcarbonylamino, halogeno (C 1 -C 6) -alkylcarbonylamino, (C 1 -C 10) -alkylsulfonylamino, halogeno (C 1 -C 10) -alkylsulfonylamino, (C 3 -C 7) -cycloalkyl- (C 1 -C 6) -alkyl- amino, cyano, hydroxy, amino, C (= O) OH,
C(=O)NHOH, SO2NH2. SO2NHCN, SO2NHOH, NHCHO, G, W2G, oder C (= O) NHOH, SO 2 NH 2. SO 2 NHCN, SO 2 NHOH, NHCHO, G, W 2 G, or
R1 bedeutet Phenyl, Phenylsulfonyl, W1-(Phenyl), W1-(O-Phenyl), W1-(S-Phenyl), W1-(SO2-Phenyl), W2-(SO2CH2-Phenyl) oder W2-(SCH2-Phenyl), wobei die Phenylringe der acht vorstehend genannten Reste jeweils s Substituenten R6 tragen, oder X1 bedeutet N oder CR2a, R 1 is phenyl, phenylsulfonyl, W 1 - (phenyl), W 1 - (O-phenyl), W 1 - (S-phenyl), W 1 - (SO 2 -phenyl), W 2 - (SO 2 CH 2 Phenyl) or W 2 - (SCH 2 -phenyl), where the phenyl rings of the eight abovementioned radicals each carry s substituents R 6 , or X 1 denotes N or CR 2a ,
X2 bedeutet N oder CR2b, R2a bedeutet Phenyl oder W3-(Phenyl), wobei die Phenylringe der zwei vorstehend genannten Reste jeweils s Substituenten R6 tragen, oder X 2 is N or CR 2b , R 2a is phenyl or W 3 - (phenyl), wherein the phenyl rings of the two radicals mentioned above each carry s substituents R 6 , or
R2a bedeutet G, W4G, Wasserstoff, Cyano, Amino, Nitro, CHO, C(=O)OH, R 2a represents G, W 4 G, is hydrogen, cyano, amino, nitro, CHO, C (= O) OH,
C(=O)NH2, C(=S)NH2, C(=O)NHCN, C(=O)NHOH, SH, SO2NH2, SO2NHCN, C (= O) NH 2 , C (= S) NH 2 , C (= O) NHCN, C (= O) NHOH, SH, SO 2 NH 2 , SO 2 NHCN,
SO2NHOH, SF5, NHCHO, NHNH2, NHOH, NHCN, NHC(O)NH2, (Ci-Cio)-Alkyl, (C2- Cio)-Alkenyl, (C2-Cio)-Alkinyl, Halogen-(Ci-Cio)-alkyl, Halogen-(C2-Cio)-alkenyl, Halogen-(C2-Cio)-alkinyl, (C3-C8)-Cycloalkyl, Halogen-(C3-C8)-cycloalkyl, (Ci-Ce)-Alkyl- (C3-C7)-cycloal kyl , (C3-C7)-Cycloal kyl-(Ci -C6)-al kyl , (C1 -C6)-Cycloal kyl-(Ci -C6)- cycloalkyl, Halogen-(Ci-C6)-Cycloalkyl-(Ci-C6)-alkyl, (Ci-C6)-Alkyl-(C3-C7)-cycloalkyl- (Ci-C6)-alkyl, (C3-C8)-Cycloalkenyl, Halogen-(C3-C8)-Cycloalkenyl, (Ci-Ce)-Alkoxy (C1- C6)-alkyl, (Ci-Ce)-Alkoxy (Ci-C6)-alkenyl, (Ci-C6)-Alkyl-(C3-C7)-cycloalkyl, (Ci-C6)- Al koxy-(C3-C7)-cycloal kyl , (C1 -C6)-Cycloal koxy-(Ci -C6)-al kyl , (C3-C7)-Cycloal koxy-(Ci- C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxy-(Ci-C6)-alkyl, (C2-C8)-Al ky Ith ioal ky I, (Ci-C6)- Alkylsulfinyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylsulfonyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylamino-(Ci- C6)-alkyl, Di-(Ci-C6)-alkylamino-(Ci-C6)-alkyl, Halogen-(Ci-C6)-alkylamino-(Ci-C6)- alkyl, (C3-C7)-Cycloalkylamino-(Ci-C6)-alkyl, (Ci-C6)-Alkyl-carbonyl, Halogen-(Ci-C6)- alkyl-carbonyl, (C3-C7)-Cycloalkyl-carbonyl, (Ci-C6)-Alkoxy-carbonyl, (C3-C7)- Cycloalkoxy-carbonyl, (C3-C7)-Cycloalkyl-(Ci-C6)-alkoxy-carbonyl, (Ci-C6)-Alkylamino- carbonyl, Di-(Ci-C6)-alkyl-amino-carbonyl, (C3-C7)-Cycloalkyl-amino-carbonyl, Cyano- (Ci-C6)-alkyl, Hydroxy-(Ci-C6)-alkyl, (C3-C7)-Cycloalkenyl-(Ci-C6)-alkyl, Halogen-(Ci- C6)-alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-halogen-alkyl, Halogen-(Ci-Ce)- alkoxy-(Ci-C6)-halogen-alkyl, Halogen-(C3-C7)-cycloalkoxy-(Ci-C6)-alkyl, (C3-C7)- Cycloalkenyloxy-(Ci-C6)-alkyl, Halogen-(C3-C7)-cycloalkenyloxy-(Ci-C6)-alkyl, Di-(Ci- C6)-alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl-carbonyl, (Ci-C6)-Alkoxy- carbonyl-(Ci-C6)-alkyl, Halogen-(Ci-C6)-alkoxy-carbonyl, (Ci-C6)-Alkoxy, Halogen-(Ci- C6)-alkoxy, (C3-C8)-Cycloalkoxy, Halogen-(C3-C8)-cycloalkoxy, (C3-C7)-Cycloalkyl-(Ci- C6)-alkoxy, (C2-C6)-Alkenyloxy, Halogen-(C2-C6)-alkenyloxy, (C2-C6)-Alkinyloxy, Halogen-(C3-C6)-alkinyloxy, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxy, (Ci-C8)-Alkyl-carbonyloxy, Halogen-(Ci-C8)-alkylcarbonyloxy, (C3-C7)-Cycloalkyl-carbonyloxy, (Ci-Ce)-Alky- carbonyl-(Ci-C6)-alkoxy, (Ci-C6)-Alkylthio, Halogen-(Ci-C6)-alkylthio, (C3-C8)-SO2NHOH, SF 5, NHCHO, NHNH 2, NHOH, NHCN, NHC (O) NH2, (Ci-Cio) alkyl, (C 2 - Cio) alkenyl, (C2 -Cio) alkynyl, halo ( C 1 -C 10) -alkyl, halogeno (C 2 -C 10) -alkenyl, halogeno (C 2 -C 10) -alkynyl, (C 3 -C 8 ) -cycloalkyl, halogeno (C 3 -C 8 ) -cycloalkyl , (C 1 -C 6 ) -alkyl (C 3 -C 7 ) -cycloalkyl, (C 3 -C 7 ) -cycloalkyl (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -cycloalkyl - (Ci-C6) - cycloalkyl, halo (Ci-C6) -cycloalkyl- (Ci-C 6) alkyl, (Ci-C 6) -alkyl- (C 3 -C 7) cycloalkyl- (C -C 6 ) -alkyl, (C 3 -C 8 ) -cycloalkenyl, halogeno (C 3 -C 8 ) -cycloalkenyl, (Ci-Ce) -alkoxy (C 1 -C 6 ) -alkyl, (Ci-Ce) alkoxy (Ci-C 6) alkenyl, (Ci-C 6) -alkyl- (C 3 -C 7) cycloalkyl, (Ci-C 6) - Al alkoxy- (C 3 -C 7) alkyl -cycloal , (C 1 -C 6 ) -cycloalkoxy (C 1 -C 6 ) -alkyl, (C 3 -C 7 ) -cycloalkoxy (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- Ci-C6) alkoxy (Ci-C 6) alkyl, (C 2 -C 8) -alkyl ky Ith ioal ky I, (Ci-C 6) - alkylsulfinyl (Ci-C 6) alkyl, ( C 1 -C 6 ) -alkylsulfonyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylamino- (C 1 -C 6 ) -alkyl, di- (C 1 -C 6 ) -alkylam ino- (Ci-C 6) alkyl, halo (Ci-C6) alkylamino (Ci-C 6) - alkyl, (C 3 -C 7) cycloalkylamino (Ci-C6) alkyl, (C -C 6 ) -alkyl-carbonyl, halo (C 1 -C 6 ) -alkyl-carbonyl, (C 3 -C 7 ) -cycloalkyl-carbonyl, (C 1 -C 6 ) -alkoxycarbonyl, (C 3 -C 7 ) - cycloalkoxycarbonyl, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 6 ) -alkoxycarbonyl, (C 1 -C 6 ) -alkylaminocarbonyl, di- (C 1 -C 6 ) -alkylaminocarbonyl, (C 3 -C 7 ) -cycloalkyl-amino-carbonyl, cyano- (C 1 -C 6 ) -alkyl, hydroxy- (C 1 -C 6 ) -alkyl, (C 3 -C 7 ) -cycloalkenyl- (C 1 -C -c 6 ) -alkyl, halogen- (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -haloalkyl, halogeno (C 1 -C 4) - alkoxy- (C 1 -C 6 ) -haloalkyl, halogeno (C 3 -C 7 ) -cycloalkoxy- (C 1 -C 6 ) -alkyl, (C 3 -C 7 ) -cycloalkenyloxy- (C 1 -C 6 ) -alkyl , Halogen- (C 3 -C 7 ) -cycloalkenyloxy- (C 1 -C 6 ) -alkyl, di- (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (Ci -C 6 ) -alkyl-carbonyl, (C 1 -C 6 ) -alkoxycarbonyl- (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkoxycarbonyl, (C 1 -C 6 ) -alkoxy, halogen- C 1 -C 6 ) alkoxy, (C 3 -C 8 ) cycloalkoxy, halo (C 3 -C 8 ) -cycloalkoxy, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 6 ) -alkoxy, (C 2 -C 6 ) -alkenyloxy, halogeno (C 2 -C 6 ) -alkenyloxy, (C 2 -C 6 ) - alkynyloxy, halo (C 3 -C 6) alkynyloxy, (Ci-C6) alkoxy (Ci-C6) alkoxy, (Ci-C 8) -alkyl-carbonyloxy, halo (Ci-C8) alkylcarbonyloxy , (C 3 -C 7) -cycloalkyl-carbonyloxy, (Ci-Ce) -Alky- carbonyl- (Ci-C 6) alkoxy, (Ci-C 6) alkylthio, halo (Ci-C 6) - alkylthio, (C 3 -C 8 ) -
Cycloalkylthio, (Ci-C6)-Alkylsulfinyl, Halogen-(Ci-C6)-alkylsulfinyl, (Ci-C6)-Alkylsulfonyl, Halogen-(Ci-C6)-alkylsulfonyl, (C3-Cio)-Cycloalkylsulfonyl, (Ci-C6)-Alkylcarbonylthio, (Ci-C6)-Alkyl(thiocarbonyl)thio, (C3-C8)-Cycloalkylsulfinyl, (Ci-C6)-Alkylaminosulfonyl, Di-(Ci-C6)-alkylaminosulfonyl, (Ci-C6)-Alkylamino, Di-(Ci-C6)-alkylamino, Halogen-(Ci- C6)-alkylamino, Halogen-di-(Ci-C6)-alkylamino, (C3-C8)-Cycloalkylamino, (C2-C8)- Alkylcarbonylamino, Halogen-(C2-C8)-alkylcarbonylamino, (Ci-Cio)-Alkylsulfonylamino, Halogen-(Ci-Cio)-alkylsulfonylamino, (C3-C7)-Cycloalkyl-(Ci-C6)-alkyl-amino oder Halogen-tri-(Ci-C4)-alkylsilyl, Cycloalkylthio, (C 1 -C 6 ) -alkylsulfinyl, halogeno (C 1 -C 6 ) -alkylsulfinyl, (C 1 -C 6 ) -alkylsulfonyl, halogeno (C 1 -C 6 ) -alkylsulfonyl, (C 3 -C 10) -cycloalkylsulfonyl, (C 1 -C 6 ) -alkylcarbonylthio, (C 1 -C 6 ) -alkyl (thiocarbonyl) thio, (C 3 -C 8 ) -cycloalkylsulfinyl, (C 1 -C 6 ) -alkylaminosulfonyl, di- (C 1 -C 6 ) -alkylaminosulfonyl, (Ci -C 6) -alkylamino, di- (C 1 -C 6) -alkylamino, halogenated C 6) -alkylamino, halo-di- (C 1 -C 6) -alkylamino, (C 3 -C 8) -cycloalkylamino, (C 2 -C 8) -alkylcarbonylamino, halogeno (C 2 -C 8) -alkylcarbonylamino, (C 1 -C 10) -alkylsulfonylamino , Halogeno (C 1 -C 10) -alkylsulfonylamino, (C 3 -C 7) -cycloalkyl- (C 1 -C 6) -alkylamino or halotri- (C 1 -C 4 ) -alkylsilyl,
R2b bedeutet Wasserstoff, Halogen, (Ci-C )-Alkyl oder (Ci-C )-Alkoxy, 1 , Q2, Q3 oder Q4, R 2b is hydrogen, halogen, (C 1 -C 4) -alkyl or (C 1 -C 4) -alkoxy, 1, Q 2 , Q 3 or Q 4 ,
Figure imgf000013_0001
Figure imgf000013_0001
R3 bedeutet (Ci-C8)-Alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, wobei diese Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Cyano, Nitro, S(O)n- (Ci-C6)-Alkyl, (Ci-Ce)-Alkoxy, Halogen-(Ci-C6)-alkoxy, (C3-C6)-Cycloalkyl, Heteroaryl, Heterocydyl oder Phenyl substituiert sind, wobei die 4 letztgenannten Reste jeweils durch p Reste aus der Gruppe bestehend aus Methyl, Ethyl, Methoxy, Trifluormethyl, Cyano und Halogen substituiert sind, und wobei Heterocydyl n Oxogruppen trägt, oder R3 bedeutet Phenyl, das jeweils durch p Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, S(O)n- (Ci-C6)-Alkyl, (Ci-Ce)-Alkoxy, Halogen-(Ci-C6)-alkoxy und (Ci-C6)-Alkoxy-(Ci-C )-alkyl substituiert ist, R 3 is (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, where these radicals are each represented by s radicals from the group consisting of halogen, cyano, nitro, S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy, (C 3 -C 6 ) -cycloalkyl, heteroaryl, heterocyclic or phenyl in which the 4 last-mentioned radicals are each substituted by p radicals from the group consisting of methyl, ethyl, methoxy, trifluoromethyl, cyano and halogen, and where heterocyclyl carries n oxo groups, or R 3 is phenyl, each being represented by p radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, S (O) n - (C 1 -C 6 ) - Alkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy and (C 1 -C 6 ) -alkoxy- (C 1 -C 4) -alkyl,
R4 bedeutet (Ci-C6)-Alkyl, (C3-C7)-cyclo-Alkyl, Halogen-(Ci-C6)-alkyl, (Ci-C6)- Alkoxy, Halogen-(Ci-C6)-alkoxy, Cyano, Nitro, Methylsulfenyl, Methylsulfinyl, R 4 is (Ci-C 6) -alkyl, (C 3 -C 7) -cycloalkyl, halo (Ci-C 6) alkyl, (Ci-C 6) - alkoxy, halo (Ci-C6 ) -alkoxy, cyano, nitro, methylsulfenyl, methylsulfinyl,
Methylsulfonyl, (Ci-C4)-Alkylcarbonylamino, Benzoylamino, Methoxycarbonyl, Methylsulfonyl, (C 1 -C 4 ) -alkylcarbonylamino, benzoylamino, methoxycarbonyl,
Ethoxycarbonyl, Benzoyl, Phenoxy, Methylcarbonyl, Piperidinylcarbonyl, Ethoxycarbonyl, benzoyl, phenoxy, methylcarbonyl, piperidinylcarbonyl,
Trifluormethylcarbonyl, Halogen, Amino, Aminocarbonyl, Methylaminocarbonyl, Dimethylanninocarbonyl, Methoxymethyl, 1 ,2,4-Triazol-1 -yl, Pyrazol-1 -yl, 2-Thiophen 2-Pyridinyl, 3-Pyridinyl, 4-Pyridinyl, 1 ,2,4-Oxadiazol-3-yl, Benzoxazol-2-yl, 1 - Ethylbenzimidazol-2-yl, Piperidin-1 -yl oder jeweils durch p Reste aus der Gruppe bestehend aus Methyl, Ethyl, Methoxy, Trifluormethyl und Halogen substituiertes Phenyl, Trifluoromethylcarbonyl, halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylanninocarbonyl, methoxymethyl, 1, 2,4-triazol-1-yl, pyrazol-1-yl, 2-thiophene 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 1, 2 , 4-oxadiazol-3-yl, benzoxazol-2-yl, 1-ethylbenzimidazol-2-yl, piperidin-1-yl or each by p radicals from the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen substituted phenyl,
R5 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (C3-C7)-Cycloalkyl, Halogen-(Ci-C6)-alkyl, (C3-C7)-Cycloalkylmethyl, Methoxycarbonylmethyl, Ethoxycarbonylmethyl, R 5 represents hydrogen, (Ci-C 6) -alkyl, (C 3 -C 7) cycloalkyl, halo (Ci-C 6) alkyl, (C3-C7) cycloalkylmethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl,
Acetylmethyl, Methoxymethyl, Methoxyethyl, Benzyl, Pyrazin-2-yl, Furan-2-yl, Acetylmethyl, methoxymethyl, methoxyethyl, benzyl, pyrazine-2-yl, furan-2-yl,
Tetrahydrofuran-2-yl, Morpholin, Dimethylamino oder durch p Reste aus der Gruppe bestehend aus Methyl, Methoxy, Trifluormethyl und Halogen substituiertes Phenyl, Tetrahydrofuran-2-yl, morpholine, dimethylamino or phenyl substituted by p radicals from the group consisting of methyl, methoxy, trifluoromethyl and halogen,
R6 bedeutet Halogen, Cyano, Hydroxy, Amino, Nitro, -CHO, -C(=O)OH, R 6 is halogen, cyano, hydroxy, amino, nitro, -CHO, -C (= O) OH,
-C(=O)NH2, -C(=S)NH2, -C(=O)NHCN, -C(=O)NHOH, -SH, -SO2NH2, -SO2NHCN, -SO2NHOH, -OCN, -SCN, -SF5, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, -C (= O) NH 2 , -C (= S) NH 2 , -C (= O) NHCN, -C (= O) NHOH, -SH, -SO 2 NH 2 , -SO 2 NHCN, -SO 2 NHOH, -OCN, -SCN, -SF 5, (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl,
Halogen-(Ci-C6)-alkyl, Halogen-(C2-C6)-alkenyl, Halogen-(C2-C6)-alkinyl, (C3-Cs)- Cycloalkyl, Halogen-(C3-C8)-cycloalkyl, (Ci-C6)-Alkyl-(C3-C7)-cycloalkyl, (C3-C7)-Halogeno (C 1 -C 6) -alkyl, halogeno (C 2 -C 6) -alkenyl, halogeno (C 2 -C 6) -alkynyl, (C 3 -C 5) -cycloalkyl, halogeno (C 3 -C 8 ) - cycloalkyl, (Ci-C6) alkyl- (C3-C7) cycloalkyl, (C 3 -C 7) -
Cycloalkyl-(Ci-C6)-alkyl, (C3-C8)-Cycloalkenyl, Halogen-(C3-C8)-cycloalkenyl, (C1-C6)- Al koxy-(Ci -C6)-al kyl , (C3-C7)-Cycloal koxy-(Ci -C6)-al kyl , (Ci -C6)-Al koxy-(Ci -C6)-al koxy- (Ci-C6)-alkyl, (Ci -C6)-Al kylth io-(Ci -C6)-al kyl , (Ci-C8)-Alkylsulfinyl-(Ci-C6)-alkyl, (Ci-C8)- Alkoxy-halogen-(Ci-C6)-alkyl, Cyano-(Ci-C6)-alkyl, Hydroxy-(Ci-C6)-alkyl, (Ci-C6)- Alkoxy, Halogen-(Ci-C6)-alkoxy, (C3-C8)-Cycloalkoxy, Halogen-(C3-C8)-cycloalkoxy, (C3-C8)-Cycloalkyl-(Ci-C6)-alkoxy, (C2-C6)-Alkenyloxy, Halogen-(C2-C6)-alkenyloxy, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxy, (C2-C6)-Alkylcarbonyloxy, (Ci-C6)-Alkylthio, Halogen- (Ci-C6)-alkylthio, (C3-C8)-Cycloal kylth io, (Ci-C6)-Alkylsulfinyl, Halogen-(Ci-Ce)- alkylsulfinyl, (Ci-C6)-Alkylsulfonyl, Halogen-(Ci-C6)-alkylsulfonyl, (C3-C8)- Cycloalkylsulfonyl, (Ci-C6)-Alkylamino, Di-(Ci-C6)-alkylamino, Halogen-(Ci-Ce)- alkylamino, Halogen-di-(Ci-C8)-alkylamino oder (C3-C8)-Cycloalkylamino, oder zwei vicinale Reste R6 bilden eine (C3-C6)-Alkylengruppe, in der p Kohlenstoffatonne durch Sauerstoff, Schwefel oder Stickstoff ersetzt sind, und in der ein Kohlenstoffatom t Oxogruppen trägt, Cycloalkyl- (Ci-C6) alkyl, (C3-C8) cycloalkenyl, halo (C3-C8) -cycloalkenyl, (C1-C6) - Al alkoxy- (Ci-C6) -alkyl, (C 3 -C 7 ) -cycloalkoxy (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy (C 1 -C 6 ) -alkoxy (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy C 6) -alkyl kylth io- (Ci-C6) -alkyl, (Ci-C8) alkylsulfinyl (Ci-C 6) alkyl, (Ci-C8) - alkoxy-halo (Ci- C 6) alkyl, cyano (Ci-C 6) alkyl, hydroxy (Ci-C 6) alkyl, (Ci-C 6) - alkoxy, halo (Ci-C6) alkoxy, (C3- C 8) cycloalkoxy, halo (C 3 -C 8) -cycloalkoxy, (C 3 -C 8) -cycloalkyl- (C 1 -C 6) -alkoxy, (C 2 -C 6) -alkenyloxy, halo (C 2 -C 6) -alkenyloxy , (Ci-C6) alkoxy (Ci-C 6) alkoxy, (C 2 -C 6) alkylcarbonyloxy, (Ci-C 6) alkylthio, halo (Ci-C 6) -alkylthio, (C 3 -C 8 ) -Cycloal kylth io, (Ci-C 6 ) alkylsulfinyl, halogen- (Ci-Ce) - alkylsulfinyl, (Ci-C 6 ) alkylsulfonyl, halo (Ci-C 6 ) alkylsulfonyl, ( C 3 -C 8 ) - cycloalkylsulfonyl, (C 1 -C 6 ) -alkylamino, di- (C 1 -C 6 ) -alkylamino, halogeno (C 1 -C 6 ) -alkylamino, halogeno-di- (C 1 -C 8 ) -alkylamino or ( C3-C8) cycloalkylamino, or two vicinal radicals R 6 form a (C 3 -C 6 ) -alkylene group in which p carbon atoms are replaced by oxygen, sulfur or nitrogen, and in which one carbon atom bears t oxo groups,
Y bedeutet O, Y is O,
W1 bedeutet (Ci-Cio)-Alkylen, (C2-C6)-Alkenylen oder (C2-C6)-Alkinylen, W2, W3 und W4 bedeuten jeweils (Ci-Cio)-Alkylen, W 1 denotes (C 1 -C 10) -alkylene, (C 2 -C 6 ) -alkenylene or (C 2 -C 6 ) -alkynylene, W 2 , W 3 and W 4 are each (C 1 -C 10) -alkylene,
G bedeutet jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-C6)-Alkoxy, Halogen-(Ci-C6)-alkoxy und (Ci-C6)-Alkoxy-(Ci-C4)-alkyl substituiertes Heteroaryl oder Heterocyclyl, wobei Heterocyclyl n Oxogruppen trägt, n bedeutet 0, 1 oder 2, p bedeutet 0, 1 , 2 oder 3, s bedeutet 0, 1 , 2, 3, 4 oder 5, t bedeutet 0 oder 1 . G represents in each case by s radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy and (C 1 -C 6 ) -alkoxy- (C 1 -C 4 ) -alkyl-substituted heteroaryl or heterocyclyl, where heterocyclyl carries n oxo groups, n denotes 0, 1 or 2, p denotes 0, 1, 2 or 3, s denotes 0, 1, 2, 3, 4 or 5, t denotes 0 or 1.
Besonders bevorzugt sind Verbindungen der allgemeinen Formel (I), worin Particular preference is given to compounds of the general formula (I) in which
R1 bedeutet (Ci-Cio)-Alkyl, (C2-Cio)-Alkenyl, (C2-Cio)-Alkinyl, Halogen-(Ci-Cio)- alkyl, Halogen-(C2-Cio)-alkenyl, Halogen-(C2-Cio)-alkinyl, (C3-Cio)-Cycloalkyl, Halogen- (C3-Cio)-cycloalkyl, (Ci-C )-Alkyl-(C3-C7)-cycloalkyl, (C3-C7)-Cycloalkyl-(Ci-C6)-alkyl, (C3-C7)-Cycloalkyl-(C3-C7)-cycloalkyl, Halogen-(C3-C7)-cycloalkyl-(Ci-C6)-alkyl, (Ci-C6)- Alkyl-(C3-C7)-cycloalkyl-(Ci-C6)-alkyl, (C3-Ci2)-Cycloalkenyl, Halogen-(C3-Ci2)- cycloalkenyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(C2-C6)-alkenyl, (Ci-C6)- Al kyl-(C3-C7)-cycloal kyl , (Ci -C6)-Al koxy-(C3-C7)-cycloal kyl , (C3-C7)-Cycloal koxy-(Ci - C6)-alkyl, (C3-C7)-Cycloalkoxy-(Ci-C6)-alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)- alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkylthio-(Ci-C6)-alkyl, (Ci-C6)-Alkylsulfinyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylsulfonyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylamino-(Ci-C6)-alkyl, Di-(Ci-Ce)- alkylamino-(Ci-C6)-alkyl, Halogen-(Ci-C6)-alkylamino-(Ci-C6)-alkyl, (C3-C7)- Cycloalkylamino-(Ci-C6)-alkyl, (Ci-C6)-Alkyl-carbonyl, Halogen-(Ci-C6)-alkyl-carbonyl, (C3-C7)-Cycloalkyl-carbonyl, (Ci-C6)-Alkoxy-carbonyl, (C3-C7)-Cycloalkoxy-carbonyl, (C3-C7)-Cycloalkyl-(Ci-C6)-alkoxy-carbonyl, (Ci-C6)-Alkylamino-carbonyl, Di-(Ci-Ce)- alkylamino-carbonyl, (C3-C7)-Cycloalkylamino-carbonyl, Cyano-(Ci-C6)-alkyl, Hydroxy- (Ci-C6)-alkyl, (C3-C7)-Cycloalkenyl-(Ci-C6)-alkyl, Halogen-(Ci-C6)-alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-halogen-(Ci-C6)-alkyl, Halogen-(Ci-C6)-alkoxy-halogen-(Ci-C6)-alkyl, Halogen-(C3-C7)-cycloalkoxy-(Ci-C6)-alkyl, (C3-C7)-Cycloalkenyloxy-(Ci-C6)-alkyl, Halogen-(C3-C7)-cycloalkenyloxy-(Ci-C6)-alkyl, Di-(Ci-C6)-alkoxy-(Ci-C6)-alkyl, (Ci-C6)- Alkoxy-(Ci-C6)-alkyl-carbonyl, (Ci-C6)-Alkoxy-carbonyl-(Ci-C6)-alkyl, Halogen-(Ci-C6)- alkoxy-carbonyl, (Ci-Cio)-Alkoxy, Halogen-(Ci-Cio)-alkoxy, (C3-Ci2)-Cycloalkoxy, Halogen-(C3-C7)-cycloalkoxy, (C3-C7)-Cycloalkyl-(Ci-C6)-alkoxy, (C2-Ci2)-Alkenyloxy, Halogen-(C2-Cio)-alkenyloxy, (C2-Cio)-Alkinyloxy, Halogen-(C3-Cio)-alkinyloxy, (C1-C6)- alkoxy-(Ci-C6)-alkoxy, (Ci-C6)-Alkyl-carbonyloxy, Halogen-(C2-Ci2)-alkyl-carbonyloxy, (C3-C7)-Cycloal kyl-carbonyloxy, (Ci -ΟΘ)-ΑΙ kyl-carbonyl-(Ci -C6)-al koxy, (Ci -C10)- Alkylthio, Halogen-(Ci-Cio)-alkylthio, (C3-Ci2)-Cycloalkylthio, (Ci-Cio)-Alkylsulfinyl, Halogen-(Ci-Cio)-alkylsulfinyl, (Ci-Cio)-alkylsulfonyl, Halogen-(Ci-Cio)-alkylsulfonyl, (C3-Ci2)-Cycloal kylsulfonyl , (Ci -C6)-Al kyl-carbonylth io, (Ci -C6)-Al kyl(th iocarbonyl )th io, (C3-Ci2)-Cycloalkylsulfinyl, (Ci-C6)-Alkylaminosulfonyl, Di-(Ci-C6)-alkylamino-sulfonyl, (Ci-C6)-Alkylamino, Di-(Ci-C6)-alkylamino, Halogen-(Ci-C6)-alkylamino, Halogen-di- (Ci-C6)-alkylamino, (C3-Ci2)-Cycloalkylamino, (Ci-C6)-Alkyl-carbonylamino, Halogen- (Ci-C6)-alkyl-carbonylamino, (Ci-Cio)-Alkylsulfonylamino, Halogen-(Ci-Cio)- alkylsulfonylamino, (C3-C7)-Cycloalkyl-(Ci-C6)-alkyl-amino, Cyano, Hydroxy, Amino,R 1 represents (C 1 -C 10) -alkyl, (C 2 -C 10) -alkenyl, (C 2 -C 10) -alkynyl, halogeno (C 1 -C 10) -alkyl, halogeno (C 2 -C 10) -alkenyl, halogen - (C 2 -C 10) -alkynyl, (C 3 -C 10) -cycloalkyl, halo (C 3 -C 10) -cycloalkyl, (C 1 -C 4 ) -alkyl (C 3 -C 7 ) -cycloalkyl, (C 3 -C 4 ) cycloalkyl, (C 3 -C 10) -cycloalkyl; 7 ) -cycloalkyl- (Ci-C 6 ) -alkyl, (C 3 -C 7 ) -cycloalkyl- (C 3 -C 7 ) -cycloalkyl, halogeno (C 3 -C 7 ) -cycloalkyl- (Ci-C 6 ) alkyl, (Ci-C6) - alkyl- (C3-C7) cycloalkyl- (Ci-C 6) alkyl, (C3-Ci2) cycloalkenyl, halo (C 3 -C 2) - Cycloalkenyl, (Ci-C6) -alkoxy- (Ci-C 6 ) -alkyl, (Ci-C6) -alkoxy- (C 2 -C 6 ) -alkenyl, (Ci-C 6 ) -Alkyl- (C 3 -C 7 ) -cycloalkyl, (C 1 -C 6 ) -alkoxy (C 3 -C 7 ) -cycloalkyl, (C 3 -C 7 ) -cycloalkoxy (C 1 -C 6 ) -alkyl, ( C 3 -C 7 -cycloalkoxy- (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl , (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylsulfinyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylsulfonyl- (C 1 -C 6 ) - alkyl, (C 1 -C 6 ) -alkylamino (C 1 -C 6 ) -alkyl, di- (C 1 -C 6 ) -alkylamino- (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkylamines no- (C 1 -C 6) -alkyl, (C 3 -C 7 ) -cycloalkylamino- (C 1 -C 6) -alkyl, (C 1 -C 6) -alkylcarbonyl, halogeno (C 1 -C 6) -alkylcarbonyl, ( C 3 -C 7 -cycloalkylcarbonyl, (C 1 -C 6) -alkoxycarbonyl, (C 3 -C 7 ) -cycloalkoxycarbonyl, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 6) -alkoxycarbonyl, (C 1 -C 6) -alkylamino-carbonyl, di- (C 1 -C 6 ) -alkylamino-carbonyl, (C 3 -C 7 ) -cycloalkylamino-carbonyl, cyano- (C 1 -C 6 ) -alkyl, hydroxy- (C 1 -C 6) ) -alkyl, (C 3 -C 7 ) -cycloalkenyl- (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy-halogen (C 1 -C 6) -alkyl, halogeno (C 1 -C 6) -alkoxy-halogeno (C 1 -C 6) -alkyl, Halo (C3-C7) cycloalkoxy (Ci-C6) alkyl, (C3-C7) -Cycloalkenyloxy- (Ci-C6) alkyl, halo (C 3 -C 7) -cycloalkenyloxy- (Ci-C6 ) -alkyl, di- (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl-carbonyl, (C 1 -C 6 ) -alkoxy carbonyl (C 1 -C 6) -alkyl, halogeno (C 1 -C 6) -alkoxycarbonyl, (C 1 -C 10) -alkoxy, halogeno (C 1 -C 10) -alkoxy, (C 3 -C 12) -cycloalkoxy, halogen (C 3 -C 7 ) -cycloalkoxy, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 6 ) -alkoxy, (C 2 -C 12) -alkenyloxy, halogeno (C 2 -C 10) -alkenyloxy, (C 2 -C 10) - Alkynyloxy, halo (C 3 -C 10) -alkynyloxy, (C 1 -C 6) -alkoxy- (C 1 -C 6) -alkoxy, (C 1 -C 6) -alkyl-carbonyloxy, halogeno (C 2 -C 12) -alkyl-carbonyloxy, (C 3 -C 7 ) -cycloalkylcarbonyloxy, (C 1 -C 6 ) -alkylcarbonyl- (C 1 -C 6) -alkoxy, (C 1 -C 10) -alkylthio, halogeno (C 1 -C 10) -alkylthio, (C 3 -C 12) -cycloalkylthio, (C 1 -C 10) -alkylsulfinyl, halogeno (C 1 -C 10) -alkylsulfinyl, (C 1 -C 10) -alkylsulfonyl, halogeno (C 1 -C 10) -alkylsulfonyl, (C 3 -C 12) ) -Cycloal kylsulfonyl, (Ci -C 6 ) -Al kyl-carbonylth io, (Ci -C 6 ) -Al kyl (th iocarbonyl) th io, (C3-Ci2) -Cycl oalkylsulfinyl, (C 1 -C 6) -alkylaminosulfonyl, di- (C 1 -C 6) -alkylaminosulfonyl, (C 1 -C 6) -alkylamino, di- (C 1 -C 6) -alkylamino, halogeno (C 1 -C 6) -alkylamino, Halo-di (Ci-C6) -alkylamino, (C3-Ci2) -cycloalkylamino, (Ci-C6) -alkyl-carbonylamino, halogeno (Ci-C6) -alkyl-carbonylamino, (Ci-Cio) -alkylsulfonylamino, Halogeno (C 1 -C 10) -alkylsulfonylamino, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 6) -alkylamino, cyano, hydroxy, amino,
C(=O)OH, C(=O)NHOH, SO2NH2. SO2NHCN, SO2NHOH, NHCHO, G, oder C (= O) OH, C (= O) NHOH, SO 2 NH 2 . SO 2 NHCN, SO 2 NHOH, NHCHO, G, or
R1 bedeutet Phenyl, W1-(Phenyl), wobei die Phenylringe jeweils s Substituenten R6 tragen, R 1 is phenyl, W 1 - (phenyl), where the phenyl rings each carry s substituents R 6 ,
X1 bedeutet N oder CR2a, X2 bedeutet N oder CR2b, R2a bedeutet Phenyl oder W3-(Phenyl), wobei die Phenylringe der zwei vorstehend genannten Reste jeweils s Substituenten R6 tragen, oder X 1 is N or CR 2a , X 2 is N or CR 2b , R 2a is phenyl or W 3 - (phenyl), wherein the phenyl rings of the two radicals mentioned above each carry s substituents R 6 , or
R2a bedeutet G, W4G, Wasserstoff, Cyano, Amino, Nitro, CHO, C(=O)OH, R 2a represents G, W 4 G, is hydrogen, cyano, amino, nitro, CHO, C (= O) OH,
C(=O)NH2, C(=S)NH2, C(=O)NHCN, C(=O)NHOH, SH, SO2NH2, SO2NHCN, C (= O) NH 2 , C (= S) NH 2 , C (= O) NHCN, C (= O) NHOH, SH, SO 2 NH 2 , SO 2 NHCN,
SO2NHOH, SF5, NHCHO, NHNH2, NHOH, NHCN, NHC(O)NH2, (Ci-Cio)-Alkyl, (C2- Cio)-Alkenyl, (C2-Cio)-Alkinyl, Halogen-(Ci-Cio)-alkyl, Halogen-(C2-Cio)-alkenyl,SO2NHOH, SF 5, NHCHO, NHNH 2, NHOH, NHCN, NHC (O) NH2, (Ci-Cio) alkyl, (C 2 - Cio) alkenyl, (C2 -Cio) alkynyl, halo ( C 1 -C 10) -alkyl, halogeno (C 2 -C 10) -alkenyl,
Halogen-(C2-Cio)-alkinyl, (C3-C8)-Cycloalkyl, Halogen-(C3-C8)-cycloalkyl, (Ci-C6)-Alkyl- (C3-C7)-cycloal kyl , (C3-C7)-Cycloal kyl-(Ci -C6)-al kyl , (Ci -C6)-Cycloal kyl-(Ci -C6)- cycloalkyl, Halogen-(Ci-C6)-Cycloalkyl-(Ci-C6)-alkyl, (Ci-C6)-Alkyl-(C3-C7)-cycloalkyl- (Ci-C6)-alkyl, (C3-C8)-Cycloalkenyl, Halogen-(C3-C8)-Cycloalkenyl, (Ci-Ce)-Alkoxy (Ci- C6)-alkyl, (Ci-C6)-Alkoxy (Ci-C6)-alkenyl, (Ci-C6)-Alkyl-(C3-C7)-cycloalkyl, (Ci-C6)- Al koxy-(C3-C7)-cycloal kyl , (Ci -C6)-Cycloal koxy-(Ci -C6)-al kyl , (C3-C7)-Cyclo-al koxy-(Ci - C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxy-(Ci-C6)-alkyl, (C2-C8)-Al ky Ith ioal ky I , (Ci-C6)- Alkylsulfinyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylsulfonyl-(Ci-C6)-alkyl, (Ci-C6)-Alkyl-amino-(Ci- C6)-alkyl, Di-(Ci-C6)-alkylamino-(Ci-C6)-alkyl, Halogen-(Ci-C6)-alkylamino-(Ci-C6)- alkyl, (C3-C7)-Cycloalkylannino-(Ci-C6)-alkyl, (Ci-C6)-Alkyl-carbonyl, Halogen-(Ci-C6)- alkyl-carbonyl, (C3-C7)-Cycloalkyl-carbonyl, (Ci-C6)-Alkoxy-carbonyl, (C3-C7)- Cycloalkoxy-carbonyl, (C3-C7)-Cycloalkyl-(Ci-C6)-alkoxy-carbonyl, (Ci-C6)-Alkylamino- carbonyl, Di-(Ci-C6)-alkyl-amino-carbonyl, (C3-C7)-Cycloalkyl-amino-carbonyl, Cyano- (Ci-C6)-alkyl, Hydroxy-(Ci-C6)-alkyl, (C3-C7)-Cycloalkenyl-(Ci-C6)-alkyl, Halogen-(Ci- C6)-alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-halogen-alkyl, Halogen-(Ci-Ce)- alkoxy-(Ci-C6)-halogen-alkyl, Halogen-(C3-C7)-cycloalkoxy-(Ci-C6)-alkyl, (C3-C7)- Cycloalkenyloxy-(Ci-C6)-alkyl, Halogen-(C3-C7)-cycloalkenyloxy-(Ci-C6)-alkyl, Di-(Ci- C6)-alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl-carbonyl, (Ci-Ce)-Alkoxy- carbonyl-(Ci-C6)-alkyl, Halogen-(Ci-C6)-alkoxy-carbonyl, (Ci-C6)-Alkoxy, Halogen-(Ci- C6)-alkoxy, (C3-C8)-Cycloalkoxy, Halogen-(C3-C8)-cycloalkoxy, (C3-C7)-Cycloalkyl-(Ci- c6)-alkoxy, (C2-C6)-Alkenyloxy, Halogen-(C2-C6)-alkenyloxy, (C2-C6)-Alkinyloxy, Halogen-(C3-C6)-alkinyloxy, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxy, (Ci-C8)-Alkyl-carbonyloxy, Halogen-(Ci-C8)-alkylcarbonyloxy, (C3-C7)-Cycloalkyl-carbonyloxy, (Ci-Ce)-Alky- carbonyl-(Ci-C6)-alkoxy, (Ci-C6)-Alkylthio, Halogen-(Ci-C6)-alkylthio, (C3-C8)-Cyclo- alkylthio, (Ci-C6)-Alkylsulfinyl, Halogen-(Ci-C6)-alkylsulfinyl, (Ci-C6)-Alkylsulfonyl, Halogen-(Ci-C6)-alkylsulfonyl, (C3-Cio)-Cycloalkylsulfonyl, (Ci-C6)-Alkylcarbonylthio, (Ci-C6)-Alkyl(thiocarbonyl)thio, (C3-C8)-Cycloalkylsulfinyl, (Ci-C6)-Alkylaminosulfonyl, Di-(Ci-C6)-alkylaminosulfonyl, (Ci-C6)-Alkylamino, Di-(Ci-C6)-alkylamino, Halogen-(Ci- C6)-alkylamino, Halogen-di-(Ci-C6)-alkylamino, (C3-C8)-Cycloalkylamino, (C2-C8)-Halo (C 2 -Cio) -alkynyl, (C 3 -C 8) cycloalkyl, halo (C 3 -C 8) cycloalkyl, (Ci-C 6) -alkyl- (C 3 -C 7) - cycloalkyl, (C 3 -C 7 ) -cycloalkyl (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -cycloalkyl (C 1 -C 6 ) -cycloalkyl, halogeno (C 1 -C 6 ) cycloalkyl (Ci-C 6) alkyl, (Ci-C6) alkyl- (C3-C7) cycloalkyl- (Ci-C 6) alkyl, (C 3 -C 8) cycloalkenyl, halogen - (C 3 -C 8 ) -cycloalkenyl, (C 1 -C 6 ) -alkoxy (ci) C 6) alkyl, (Ci-C 6) alkoxy (Ci-C 6) alkenyl, (Ci-C6) alkyl- (C 3 -C 7) cycloalkyl, (Ci-C 6) - Al koxy - (C 3 -C 7) -cycloal kyl, (Ci-C6) -Cycloal alkoxy- (Ci-C6) -alkyl, (C 3 -C 7) -cycloalkyl al alkoxy- (Ci - C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 2 -C 8 ) -alkyl, aklyl, ky I, (C 1 -C 6 ) - alkylsulfinyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylsulfonyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkyl-amino- (C 1 -C 6 ) -alkyl, di - (Ci-C6) alkylamino (Ci-C6) alkyl, halo (Ci-C6) alkylamino (Ci-C 6) - alkyl, (C 3 -C 7) -Cycloalkylannino- (Ci- C6) alkyl, (Ci-C 6) -alkyl-carbonyl, halo (Ci-C6) - alkyl-carbonyl, (C 3 -C 7) -cycloalkyl-carbonyl, (Ci-C6) alkoxy-carbonyl , (C 3 -C 7 ) -cycloalkoxycarbonyl, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 6 ) -alkoxycarbonyl, (C 1 -C 6 ) -alkylaminocarbonyl, di- (C 1 -C 6 ) -alkyl-amino-carbonyl, (C 3 -C 7 ) -cycloalkyl-amino-carbonyl, cyano- (C 1 -C 6 ) -alkyl, hydroxy- (C 1 -C 6 ) -alkyl, (C 3 -C 7 ) Cycloalkenyl- (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy y (Ci-C 6) -halogen-alkyl, halo (Ci-Ce) - alkoxy- (Ci-C6) -halogen-alkyl, halo (C 3 -C 7) cycloalkoxy (Ci-C6) alkyl, (C 3 -C 7 ) -cycloalkenyloxy- (C 1 -C 6 ) -alkyl, halogeno (C 3 -C 7 ) -cycloalkenyloxy- (C 1 -C 6 ) -alkyl, di- (C 1 -C 6 ) -alkoxy (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl-carbonyl, (C 1 -C 6 ) -alkoxycarbonyl- (C 1 -C 6 ) -alkyl, halogen- (C 1 -C 6 ) -alkyl C 1 -C 6) -alkoxycarbonyl, (C 1 -C 6) -alkoxy, halogeno (C 1 -C 6) -alkoxy, (C 3 -C 8) -cycloalkoxy, halogeno (C 3 -C 8) -cycloalkoxy, (C 3 -C 7 ) -cycloalkyl- (C 6 -C 6 ) -alkoxy, (C 2 -C 6) -alkenyloxy, halo (C 2 -C 6) -alkenyloxy, (C 2 -C 6) -alkynyloxy, halogen- (C 3 -C 6) - alkynyloxy, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkoxy, (C 1 -C 8) -alkyl-carbonyloxy, halogeno (C 1 -C 8) -alkylcarbonyloxy, (C 3 -C 7 ) -cycloalkyl-carbonyloxy, (Ci-Ce) -Alky- carbonyl- (Ci-C 6) alkoxy, (Ci-C 6) alkylthio, halo (Ci-C 6) -alkylthio, (C 3 -C 8) cyclo- alkylthio , (C 1 -C 6 ) -alkylsulfinyl, halogeno (C 1 -C 6 ) -alkylsulfinyl, (C 1 -C 6 ) -alkylsulfonyl, halogeno (C 1 -C 6 ) -alkylsulfonyl, (C 3 -C 10) -cycloalkylsulfonyl, ( Ci-C6) Alkylcarbonylthio, (C 1 -C 6) -alkyl (thiocarbonyl) thio, (C 3 -C 8) -cycloalkylsulfinyl, (C 1 -C 6) -alkylaminosulfonyl, di- (C 1 -C 6) -alkylaminosulfonyl, (C 1 -C 6) -alkylamino, Di- (C 1 -C 6) -alkylamino, halogeno (C 1 -C 6) -alkylamino, halo-di- (C 1 -C 6) -alkylamino, (C 3 -C 8) -cycloalkylamino, (C 2 -C 8) -
Alkylcarbonylamino, Halogen-(C2-C8)-alkylcarbonylamino, (Ci-Cio)-Alkylsulfonylamino, Halogen-(Ci-Cio)-alkylsulfonylamino, (C3-C7)-Cycloalkyl-(Ci-C6)-alkyl-amino oder Halogen-tri-(Ci-C4)-alkylsilyl, R2b bedeutet Wasserstoff, Halogen, (Ci-C )-Alkyl oder (Ci-C )-Alkoxy, Alkylcarbonylamino, halogeno (C 2 -C 8) -alkylcarbonylamino, (C 1 -C 10) -alkylsulfonylamino, halogeno (C 1 -C 10) -alkylsulfonylamino, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 6 ) -alkyl-amino or Halo-tri (C 1 -C 4 ) -alkylsilyl, R 2b is hydrogen, halogen, (C 1 -C 4) -alkyl or (C 1 -C 4) -alkoxy,
Q bedeutet einen Rest Q1, Q2, Q3 oder Q4
Figure imgf000018_0001
Q is a radical Q 1 , Q 2 , Q 3 or Q 4
Figure imgf000018_0001
R3 bedeutet jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Cyano, Nitro, S(0)n-(Ci-C6)-Alkyl, (Ci-C6)-Alkoxy und Halogen-(Ci-C6)-alkoxy substituiertes (Ci-C8)-Alkyl, (C2-C8)-Alkenyl oder (C2-C8)-Alkinyl, R 3 represents in each case by s radicals from the group consisting of halogen, cyano, nitro, S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy and halogen- (C 1 -C 6 ) - alkoxy-substituted (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl or (C 2 -C 8 ) -alkynyl,
R4 bedeutet (Ci-C6)-Alkyl, (C3-C7)-cyclo-Alkyl, Halogen-(Ci-C6)-alkyl, (Ci-C6)- Alkoxy, Halogen-(Ci-C6)-alkoxy, Cyano, Nitro, Methylsulfenyl, Methylsulfinyl, R 4 is (C 1 -C 6 ) -alkyl, (C 3 -C 7 ) -cycloalkyl, halogeno (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) alkoxy, cyano, nitro, methylsulfenyl, methylsulfinyl,
Methylsulfonyl, (Ci-C4)-Alkylcarbonylamino, Benzoylamino, Methoxycarbonyl, Methylsulfonyl, (C 1 -C 4 ) -alkylcarbonylamino, benzoylamino, methoxycarbonyl,
Ethoxycarbonyl, Benzoyl, Phenoxy, Methylcarbonyl, Piperidinylcarbonyl, Ethoxycarbonyl, benzoyl, phenoxy, methylcarbonyl, piperidinylcarbonyl,
Trifluormethylcarbonyl, Halogen, Amino, Aminocarbonyl, Methylaminocarbonyl, Dimethylanninocarbonyl, Methoxymethyl, 1 ,2,4-Triazol-1 H, 1 -Pyrazol-1 H, 2-Thiophenyl, 2-Pyridinyl, 3-Pyridinyl, 4-Pyridinyl, 1 ,2,4-Oxadiazol-3-yl, Benzoxazol-2-yl, 1 - Ethylbenzimidazol-2-yl, Piperidin-1 -yl oder jeweils durch s Reste aus der Gruppe bestehend aus Methyl, Ethyl, Methoxy, Trifluormethyl und Halogen substituiertes Phenyl,  Trifluoromethylcarbonyl, halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylanninocarbonyl, methoxymethyl, 1, 2,4-triazole-1H, 1-pyrazole-1H, 2-thiophenyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 1, 2,4-oxadiazol-3-yl, benzoxazol-2-yl, 1-ethylbenzimidazol-2-yl, piperidin-1-yl or phenyl substituted by s radicals selected from the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen .
R5 bedeutet Wassetrstoff, (Ci-C6)-Alkyl, (C3-C7)-Cycloalkyl, Halogen-(Ci-C6)- alkyl, (C3-C7)-Cycloalkylmethyl, Methoxycarbonylmethyl, Ethoxycarbonylmethyl, Acetylmethyl, Methoxymethyl, Methoxyethyl, Benzyl, Pyrazin-2-yl, Furan-2-yl, R 5 represents Wassetrstoff, (Ci-C 6) -alkyl, (C 3 -C 7) cycloalkyl, halo (Ci-C 6) - alkyl, (C3-C7) cycloalkylmethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, acetylmethyl, Methoxymethyl, methoxyethyl, benzyl, pyrazine-2-yl, furan-2-yl,
Tetrahydrofuran-2-yl, Morpholin, Dimethylamino oder durch p Reste aus der Gruppe bestehend aus Methyl, Methoxy, Trifluormethyl und Halogen substituiertes Phenyl,  Tetrahydrofuran-2-yl, morpholine, dimethylamino or phenyl substituted by p radicals from the group consisting of methyl, methoxy, trifluoromethyl and halogen,
R6 bedeutet Halogen, Cyano, Nitro, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, (Ci-Ce)-Alkoxy, Halogen-(Ci-C6)-alkoxy, (Ci- Ce)-Al kylthio, (Ci-Ce)-Al kylsulfinyl, (Ci-CeJ-Alkylsulfonyl, Phenyl, Methylendioxo, R 6 is halogen, cyano, nitro, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, halogeno (C 1 -C 6 ) -alkyl, (C 3 -C 4 ) -alkyl, C 6 ) -cycloalkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkylthio, (C 1 -C 6 ) -alkylsulfinyl, (C 1 -C 6 -alkylsulfonyl, Phenyl, methylene dioxo,
Y bedeutet O, W1 bedeutet (Ci-Cio)-Alkylen, W2, W3 und W4 bedeuten jeweils (Ci-Cio)-Alkylen, Y is O, W 1 is (C 1 -C 10) -alkylene, W 2 , W 3 and W 4 are each (C 1 -C 10) -alkylene,
G bedeutet jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C3)-alkyl, Cyclopropyl, S(O)n-(Ci-C3)-Alkyl, (Ci-C )- Alkoxy, Halogen-(Ci-C4)-alkoxy und (Ci-C4)-Alkoxy-(Ci-C4)-alkyl substituiertes G is in each case represented by s radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 3 ) -alkyl, cyclopropyl, S (O) n - (C 1 -C 3 ) -Alkyl, (Ci-C) - alkoxy, halogen- (Ci-C 4 ) -alkoxy and (Ci-C 4 ) -alkoxy- (Ci-C 4 ) -alkyl substituted
Heteroaryl oder Heterocyclyl, wobei Heterocyclyl n Oxogruppen trägt, n bedeutet 0, 1 oder 2, p bedeutet 0, 1 , 2 oder 3, s bedeutet 0, 1 , 2, 3, 4 oder 5. Heteroaryl or heterocyclyl, wherein heterocyclyl carries n oxo groups, n means 0, 1 or 2, p means 0, 1, 2 or 3, s means 0, 1, 2, 3, 4 or 5.
In allen nachfolgend genannten Formeln haben die Substituenten und Symbole, sofern nicht anders definiert, dieselbe Bedeutung wie unter Formel (I) beschrieben. In all of the formulas below, the substituents and symbols, unless otherwise defined, have the same meaning as described for formula (I).
Erfindungsgemäße Verbindungen können beispielsweise gemäß Schema 1 nach den in WO 2012/148622 A1 angegebenen Methoden hergestellt werden. Diese Methoden umfassen die Umsetzung einer Säure (III) mit einem Amin Q-H und die Umsetzung eines Säurechlorids (II) mit einem Amin Q-H. Compounds according to the invention can be prepared, for example, according to Scheme 1 by the methods given in WO 2012/148622 A1. These methods include the reaction of an acid (III) with an amine QH and the reaction of an acid chloride (II) with an amine QH.
Schema 1 Scheme 1
Figure imgf000020_0001
Figure imgf000020_0001
Die benötigten Azin-2-on-3-carbonsäurechloride (II) beziehungsweise die ihnen zugrunde liegenden Azin-2-on-3-carbonsäuren (III) können z.B. nach den in WO 2012/148622 A1 beschriebenen Methoden hergestellt werden. The required azin-2-one-3-carboxylic acid chlorides (II) or their underlying azin-2-one-3-carboxylic acids (III) may be e.g. be prepared according to the methods described in WO 2012/148622 A1.
Es kann zweckmäßig sein, Reaktionsschritte in ihrer Reihenfolge zu ändern. So sind Benzoesäuren, die ein Sulfoxid tragen, nicht ohne weiteres in ihre Säurechloride zu überführen. Hier bietet sich an, zunächst auf Thioether-Stufe das Amid zu herzustellen und danach den Thioether zum Sulfoxid zu oxidieren. It may be convenient to change reaction steps in order. Thus, benzoic acids carrying a sulfoxide are not readily converted into their acid chlorides. Here it is advisable to first produce the amide on the thioether stage and then to oxidize the thioether to the sulfoxide.
Kollektionen aus Verbindungen der Formel (I) und/oder deren Salzen, die nach den oben genannten Reaktionen synthetisiert werden können, können auch in Collections of compounds of the formula (I) and / or their salts, which can be synthesized after the abovementioned reactions, can also be found in
parallelisierter Weise hergestellt werden, wobei dies in manueller, teilweise be prepared in a parallelized manner, this manual, in part
automatisierter oder vollständig automatisierter Weise geschehen kann. Dabei ist es beispielsweise möglich, die Reaktionsdurchführung, die Aufarbeitung oder die automated or completely automated way. It is possible, for example, the reaction procedure, the work-up or the
Reinigung der Produkte bzw. Zwischenstufen zu automatisieren. Insgesamt wird hierunter eine Vorgehensweise verstanden, wie sie beispielsweise durch D. Tiebes in Combinatorial Chemistry - Synthesis, Analysis, Screening (Herausgeber Günther Jung), Verlag Wiley 1999, auf den Seiten 1 bis 34 beschrieben ist. Zur parallelisierten Reaktionsdurchführung und Aufarbeitung können eine Reihe von im Handel erhältlichen Geräten verwendet werden, beispielsweise Calpyso- Reaktionsblöcke (Caylpso reaction blocks) der Firma Barnstead International, Automate cleaning of products or intermediates. Overall, this is understood to mean a procedure as described, for example, by D. Tiebes in Combinatorial Chemistry - Synthesis, Analysis, Screening (publisher Günther Jung), Verlag Wiley 1999, on pages 1 to 34. For the parallelized reaction procedure and workup, a number of commercially available devices can be used, for example Calypyso reaction blocks (Caylpso reaction blocks) from Barnstead International,
Dubuque, Iowa 52004-0797, USA oder Reaktionsstationen (reaction stations) der Firma Radleys, Shirehill, Saffron Waiden, Essex, CB 1 1 3AZ, England oder Dubuque, Iowa 52004-0797, USA or reaction stations from Radleys, Shirehill, Saffron Waiden, Essex, CB 1 1 3AZ, England or
MultiPROBE Automated Workstations der Firma Perkin Elmar, Waltham, MultiPROBE Automated Workstations from Perkin Elmar, Waltham,
Massachusetts 02451 , USA. Für die parallelisierte Aufreinigung von Verbindungen der allgemeinen Formel (I) und deren Salzen beziehungsweise von bei der Herstellung anfallenden Zwischenprodukten stehen unter anderem Chromatographieapparaturen zur Verfügung, beispielsweise der Firma ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA. Massachusetts 02451, United States. For the parallelized purification of compounds of the general formula (I) and their salts or of intermediates obtained during the preparation, among others, chromatography apparatuses are available, for example the company ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA.
Die aufgeführten Apparaturen führen zu einer modularen Vorgehensweise, bei der die einzelnen Arbeitsschritte automatisiert sind, zwischen den Arbeitsschritten jedoch manuelle Operationen durchgeführt werden müssen. Dies kann durch den Einsatz von teilweise oder vollständig integrierten Automationssystemen umgangen werden, bei denen die jeweiligen Automationsmodule beispielsweise durch Roboter bedient werden. Derartige Automationssysteme können zum Beispiel von der Firma Caliper, Hopkinton, MA 01748, USA bezogen werden. The listed equipment leads to a modular procedure, in which the individual work steps are automated, but between the work steps, manual operations must be performed. This can be circumvented by the use of partially or fully integrated automation systems in which the respective automation modules are operated, for example, by robots. Such automation systems can be obtained, for example, from Caliper, Hopkinton, MA 01748, USA.
Die Durchführung einzelner oder mehrerer Syntheseschritte kann durch den Einsatz von Polymer-supported reagents/Scavanger-Harze unterstützt werden. In der The implementation of single or multiple synthetic steps can be supported by the use of polymer-supported reagents / Scavanger resins. In the
Fachliteratur sind eine Reihe von Versuchsprotokollen beschrieben, beispielsweise in ChemFiles, Vol. 4, No. 1 , Polymer-Supported Scavengers and Reagents for Solution- Phase Synthesis (Sigma-Aldrich). Technical literature describes a number of experimental protocols, for example in ChemFiles, Vol. 1, Polymer-Supported Scavengers and Reagents for Solution-Phase Synthesis (Sigma-Aldrich).
Neben den hier beschriebenen Methoden kann die Herstellung von Verbindungen der allgemeinen Formel (I) und deren Salzen vollständig oder partiell durch Festphasen unterstützte Methoden erfolgen. Zu diesem Zweck werden einzelne Zwischenstufen oder alle Zwischenstufen der Synthese oder einer für die entsprechende In addition to the methods described herein, the preparation of compounds of general formula (I) and their salts can be carried out fully or partially by solid-phase assisted methods. For this purpose, individual intermediates or all intermediates of the synthesis or one for the corresponding
Vorgehensweise angepassten Synthese an ein Syntheseharz gebunden. Festphasen- unterstützte Synthesemethoden sind in der Fachliteratur hinreichend beschrieben, z.B. Barry A. Bunin in "The Combinatorial Index", Verlag Academic Press, 1998 und  Approach adapted synthesis bound to a synthetic resin. Solid phase assisted synthetic methods are well described in the literature, e.g. Barry A. Bunin in "The Combinatorial Index", Academic Press, 1998 and
Combinatorial Chemistry - Synthesis, Analysis, Screening (Herausgeber Günther Jung), Verlag Wiley, 1999. Die Verwendung von Festphasen- unterstützten Combinatorial Chemistry - Synthesis, Analysis, Screening (Editor Günther Jung), Wiley, 1999. The Use of Solid Phase Assisted
Synthesemethoden erlaubt eine Reihe von literaturbekannten Protokollen, die wiederum manuell oder automatisiert ausgeführt werden können. Die Reaktionen können beispielsweise mittels IRORI-Technologie in Mikroreaktoren (microreactors) der Firma Nexus Biosystems, 12140 Community Road, Poway, CA92064, USA durchgeführt werden. Synthesis methods allow a number of protocols known from the literature, which in turn can be carried out manually or automatically. The reactions can be carried out, for example, by means of IRORI technology in microreactors (microreactors) from Nexus Biosystems, 12140 Community Road, Poway, CA92064, USA.
Sowohl an fester als auch in flüssiger Phase kann die Durchführung einzelner oder mehrerer Syntheseschritte durch den Einsatz der Mikrowellen-Technologie unterstützt werden. In der Fachliteratur sind eine Reihe von Versuchsprotokollen beschrieben, beispielsweise in Microwaves in Organic and Medicinal Chemistry (Herausgeber C. O. Kappe und a. Stadler), Verlag Wiley, 2005. Both solid and liquid phases can be supported by the implementation of single or multiple synthetic steps through the use of microwave technology. A number of experimental protocols are described in the specialist literature, for example in Microwaves in Organic and Medicinal Chemistry (publishers C. O. Kappe and A. Stadler), Verlag Wiley, 2005.
Die Herstellung gemäß der hier beschriebenen Verfahren liefert Verbindungen der Formel (I) und deren Salze in Form von Substanzkollektionen, die Bibliotheken genannt werden. Gegenstand der vorliegenden Erfindung sind auch Bibliotheken, die mindestens zwei Verbindungen der Formel (I) und deren Salzen enthalten. The preparation according to the methods described herein provides compounds of formula (I) and their salts in the form of substance collections called libraries. The present invention also provides libraries containing at least two compounds of formula (I) and their salts.
Die erfindungsgemäßen Verbindungen weisen eine ausgezeichnete herbizide The compounds of the invention have an excellent herbicidal
Wirksamkeit gegen ein breites Spektrum wirtschaftlich wichtiger mono- und dikotyler annueller Schadpflanzen auf. Auch schwer bekämpfbare perennierende Effectiveness against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful plants. Also difficult to combat perennial
Schadpflanzen, die aus Rhizomen, Wurzelstöcken oder anderen Dauerorganen austreiben, werden durch die Wirkstoffe gut erfasst. Harmful plants that drive off rhizomes, rhizomes or other permanent organs are well detected by the active ingredients.
Gegenstand der vorliegenden Erfindung ist daher auch ein Verfahren zur Bekämpfung von unerwünschten Pflanzen oder zur Wachstumsregulierung von Pflanzen, vorzugsweise in Pflanzenkulturen, worin eine oder mehrere erfindungsgemäße  The present invention therefore also provides a method for controlling unwanted plants or for regulating the growth of plants, preferably in plant crops, wherein one or more of the present invention
Verbindung(en) auf die Pflanzen (z.B. Schadpflanzen wie mono- oder dikotyle Compound (s) on the plants (e.g., weeds such as mono- or dicotyledons
Unkräuter oder unerwünschte Kulturpflanzen), das Saatgut (z.B. Körner, Samen oder vegetative Vermehrungsorgane wie Knollen oder Sprossteile mit Knospen) oder die Fläche, auf der die Pflanzen wachsen (z.B. die Anbaufläche), ausgebracht werden. Dabei können die erfindungsgemäßen Verbindungen z.B. im Vorsaat- (ggf. auch durch Einarbeitung in den Boden), Vorauflauf- oder Nachauflaufverfahren ausgebracht werden. Im Einzelnen seien beispielhaft einige Vertreter der mono- und dikotylen Unkrautflora genannt, die durch die die erfindungsgemäßen Verbindungen kontrolliert werden können, ohne dass durch die Nennung eine Beschränkung auf bestimmte Arten erfolgen soll. Weeds or unwanted crops), the seeds (eg grains, seeds or vegetative propagules such as tubers or sprout parts with buds) or the area on which the plants grow (eg the acreage) are applied. The compounds according to the invention can be applied, for example, in pre-sowing (optionally also by incorporation into the soil), pre-emergence or postemergence process. Specifically, by way of example, some representatives of the monocotyledonous and dicotyledonous weed flora may be mentioned which control the compounds according to the invention without being restricted to certain species.
Monokotyle Schadpflanzen der Gattungen: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria und Sorghum.  Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata , Ishamedum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, and Sorghum.
Dikotyle Unkräuter der Gattungen: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum,  Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum,
Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola und Xanthium. Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola and Xanthium.
Werden die erfindungsgemäßen Verbindungen vor dem Keimen auf die Erdoberfläche appliziert, so wird entweder das Auflaufen der Unkrautkeimlinge vollständig verhindert oder die Unkräuter wachsen bis zum Keimblattstadium heran, stellen jedoch dann ihr Wachstum ein und sterben schließlich nach Ablauf von drei bis vier Wochen If the compounds according to the invention are applied to the surface of the earth prior to germination, either the emergence of the weed seedlings is completely prevented or the weeds grow up to the cotyledon stage, but then stop their growth and finally die after three to four weeks
vollkommen ab. completely off.
Bei Applikation der Wirkstoffe auf die grünen Pflanzenteile im Nachauflaufverfahren tritt nach der Behandlung Wachstumsstop ein und die Schadpflanzen bleiben in dem zum Applikationszeitpunkt vorhandenen Wachstumsstadium stehen oder sterben nach einer gewissen Zeit ganz ab, so dass auf diese Weise eine für die Kulturpflanzen schädliche Unkrautkonkurrenz sehr früh und nachhaltig beseitigt wird.  When the active ingredients are applied to the green parts of the plants postemergence, growth stops after the treatment and the harmful plants remain in the growth stage existing at the time of application or die completely after a certain time, so that a weed competition harmful to the crop plants takes place very early and sustainably eliminated.
Obgleich die erfindungsgemäßen Verbindungen eine ausgezeichnete herbizide Aktivität gegenüber mono- und dikotylen Unkräutern aufweisen, werden Kulturpflanzen wirtschaftlich bedeutender Kulturen z.B. dikotyler Kulturen der Gattungen Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Although the compounds of the present invention have excellent herbicidal activity against mono- and dicotyledonous weeds, crops of economically important crops, e.g. dicotyledonous cultures of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium,
Ipomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, oder monokotyler Kulturen der Gattungen Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Seeale, Sorghum, Triticale, Triticum, Zea, insbesondere Zea und Triticum, abhängig von der Struktur der jeweiligen erfindungsgemäßen Verbindung und deren Aufwandmenge nur unwesentlich oder gar nicht geschädigt. Die vorliegenden Verbindungen eignen sich aus diesen Gründen sehr gut zur selektiven Bekämpfung von unerwünschtem Pflanzenwuchs in Ipomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotylic cultures of the genera Allium, Pineapple, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Seeale, Sorghum, Triticale, Triticum, Zea, in particular Zea and Triticum, depending on the structure of the respective compound of the invention and their application rate only insignificantly or not at all damaged. For these reasons, the present compounds are very well suited for the selective control of undesired plant growth in
Pflanzenkulturen wie landwirtschaftlichen Nutzpflanzungen oder Zierpflanzungen. Crops such as agricultural crops or ornamental plantings.
Darüber hinaus weisen die erfindungsgemäßen Verbindungen, abhängig von ihrer jeweiligen chemischen Struktur und der ausgebrachten Aufwandmenge, In addition, the compounds of the invention, depending on their respective chemical structure and the applied application rate,
hervorragende wachstumsregulatorische Eigenschaften bei Kulturpflanzen auf. Sie greifen regulierend in den pflanzeneigenen Stoffwechsel ein und können damit zur gezielten Beeinflussung von Pflanzeninhaltsstoffen und zur Ernteerleichterung wie z.B. durch Auslösen von Desikkation und Wuchsstauchung eingesetzt werden. Des excellent growth regulatory properties in crops. They regulate the plant's metabolism and can thus be used to specifically influence plant constituents and facilitate harvesting, such as be used by triggering desiccation and stunted growth. Of
Weiteren eignen sie sich auch zur generellen Steuerung und Hemmung von Furthermore, they are also suitable for the general control and inhibition of
unerwünschtem vegetativen Wachstum, ohne dabei die Pflanzen abzutöten. Eine Hemmung des vegetativen Wachstums spielt bei vielen mono- und dikotylen Kulturen eine große Rolle, da beispielsweise die Lagerbildung hierdurch verringert oder völlig verhindert werden kann. undesirable vegetative growth without killing the plants. Inhibition of vegetative growth plays an important role in many monocotyledonous and dicotyledonous crops, since, for example, storage formation can thereby be reduced or completely prevented.
Aufgrund ihrer herbiziden und pflanzenwachstumsregulatorischen Eigenschaften können die Wirkstoffe auch zur Bekämpfung von Schadpflanzen in Kulturen von gentechnisch oder durch konventionelle Mutagenese veränderten Pflanzen eingesetzt werden. Die transgenen Pflanzen zeichnen sich in der Regel durch besondere vorteilhafte Eigenschaften aus, beispielsweise durch Resistenzen gegenüber bestimmten Pestiziden, vor allem bestimmten Herbiziden, Resistenzen gegenüber Pflanzenkrankheiten oder Erregern von Pflanzenkrankheiten wie bestimmten Insekten oder Mikroorganismen wie Pilzen, Bakterien oder Viren. Andere besondere Because of their herbicidal and plant growth regulatory properties, the active compounds can also be used to control harmful plants in crops of genetically engineered or conventional mutagenized plants. The transgenic plants are usually characterized by particular advantageous properties, for example by resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses. Other special
Eigenschaften betreffen z.B. das Erntegut hinsichtlich Menge, Qualität, Lagerfähigkeit, Zusammensetzung und spezieller Inhaltsstoffe. So sind transgene Pflanzen mit erhöhtem Stärkegehalt oder veränderter Qualität der Stärke oder solche mit anderer Fettsäurezusammensetzung des Ernteguts bekannt. Properties relate to e.g. the crop in terms of quantity, quality, shelf life, composition and special ingredients. Thus, transgenic plants with increased starch content or altered quality of the starch or those with other fatty acid composition of the crop are known.
Bevorzugt bezüglich transgener Kulturen ist die Anwendung der erfindungsgemäßen Verbindungen in wirtschaftlich bedeutenden transgenen Kulturen von Nutz- undPreferred with respect to transgenic cultures is the use of the compounds of the invention in economically important transgenic crops of useful and
Zierpflanzen, z.B. von Getreide wie Weizen, Gerste, Roggen, Hafer, Hirse, Reis und Mais oder auch Kulturen von Zuckerrübe, Baumwolle, Soja, Raps, Kartoffel, Maniok, Tomate, Erbse und anderen Gemüsesorten. Ornamental plants, eg of cereals such as wheat, barley, rye, oats, millet, rice and maize or also crops of sugar beet, cotton, soya, rapeseed, potato, cassava, Tomato, pea and other vegetables.
Vorzugsweise können die erfindungsgemäßen Verbindungen als Herbizide in Preferably, the compounds of the invention as herbicides in
Nutzpflanzenkulturen eingesetzt werden, welche gegenüber den phytotoxischen Wirkungen der Herbizide resistent sind bzw. gentechnisch resistent gemacht worden sind. Crop plants are used, which are resistant to the phytotoxic effects of herbicides or have been made genetically resistant.
Herkömmliche Wege zur Herstellung neuer Pflanzen, die im Vergleich zu bisher vorkommenden Pflanzen modifizierte Eigenschaften aufweisen, bestehen Conventional ways of producing new plants that have modified properties compared to previously occurring plants exist
beispielsweise in klassischen Züchtungsverfahren und der Erzeugung von Mutanten. Alternativ können neue Pflanzen mit veränderten Eigenschaften mit Hilfe for example, in classical breeding methods and the generation of mutants. Alternatively, new plants with altered properties can help
gentechnischer Verfahren erzeugt werden (siehe z. B. EP-A-0221044, EP-A-0131624). Beschrieben wurden beispielsweise in mehreren Fällen genetic engineering methods are produced (see eg EP-A-0221044, EP-A-0131624). For example, several cases have been described
gentechnische Veränderungen von Kulturpflanzen zwecks Modifikation der in den Pflanzen synthetisierten Stärke (z. B. WO 92/1 1376, WO 92/14827, WO 91/19806),  genetic engineering of crops for modification of the starch synthesized in the plants (eg WO 92/1 1376, WO 92/14827, WO 91/19806),
- transgene Kulturpflanzen, welche gegen bestimmte Herbizide vom Typ transgenic crops which are resistant to certain herbicides of the
Glufosinate (vgl. z. B. EP-A-0242236, EP-A-242246) oder Glyphosate  Glufosinate (see, for example, EP-A-0242236, EP-A-242246) or glyphosate
(WO 92/00377) oder der Sulfonylharnstoffe (EP-A-0257993, US-A-5013659) resistent sind  (WO 92/00377) or the sulfonylureas (EP-A-0257993, US-A-5013659) are resistant
transgene Kulturpflanzen, beispielsweise Baumwolle, mit der Fähigkeit  transgenic crops, for example cotton, with the ability
Bacillus thuringiensis-Toxine (Bt-Toxine) zu produzieren, welche die  Bacillus thuringiensis toxins (Bt toxins) to produce, which the
Pflanzen gegen bestimmte Schädlinge resistent machen (EP-A-0142924, EP-A-0193259).  Make plants resistant to certain pests (EP-A-0142924, EP-A-0193259).
transgene Kulturpflanzen mit modifizierter Fettsäurezusammensetzung (WO 91/13972).  Transgenic crop plants with modified fatty acid composition (WO 91/13972).
gentechnisch veränderte Kulturpflanzen mit neuen Inhalts- oder  genetically modified crops with new content or
Sekundärstoffen z. B. neuen Phytoalexinen, die eine erhöhte  Secondary materials z. B. new phytoalexins, which increased one
Krankheitsresistenz verursachen (EPA 309862, EPA0464461 )  Disease resistance cause (EPA 309862, EPA0464461)
gentechnisch veränderte Pflanzen mit reduzierter Photorespiration, die höhere Erträge und höhere Stresstoleranz aufweisen (EPA 0305398).  genetically modified plants with reduced photorespiration, which have higher yields and higher stress tolerance (EPA 0305398).
Transgene Kulturpflanzen, die pharmazeutisch oder diagnostisch wichtige Proteine produzieren („molecular pharming") transgene Kulturpflanzen, die sich durch höhere Erträge oder bessere Qualität auszeichnen Transgenic crop plants that produce pharmaceutically or diagnostically important proteins ("molecular pharming") Transgenic crops that are characterized by higher yields or better quality
transgene Kulturpflanzen die sich durch eine Kombinationen z. B. der o. g. neuen Eigenschaften auszeichnen („gene stacking")  transgenic crops characterized by a combination z. B. the o. G. characterize new properties ("gene stacking")
Zahlreiche molekularbiologische Techniken, mit denen neue transgene Pflanzen mit veränderten Eigenschaften hergestellt werden können, sind im Prinzip bekannt, siehe z. B. I. Potrykus und G. Spangenberg (eds.) Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg, oder Christou, "Trends in Plant Science" 1 (1996) 423-431 ). Numerous molecular biological techniques that can be used to produce novel transgenic plants with altered properties are known in principle. B. I. Potrykus and G. Spangenberg (eds.) Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg, or Christou, "Trends in Plant Science" 1 (1996) 423-431).
Für derartige gentechnische Manipulationen können Nucleinsäuremoleküle in For such genetic manipulations, nucleic acid molecules can be used in
Plasmide eingebracht werden, die eine Mutagenese oder eine Sequenzveränderung durch Rekombination von DNA-Sequenzen erlauben. Mit Hilfe von Standardverfahren können z. B. Basenaustausche vorgenommen, Teilsequenzen entfernt oder natürliche oder synthetische Sequenzen hinzugefügt werden. Für die Verbindung der DNA- Fragmente untereinander können an die Fragmente Adaptoren oder Linker angesetzt werden, siehe z. B. Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2 Aufl. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY, oder Winnacker "Gene und Klone", VCH Weinheim 2. Auflage 1996 Plasmids are introduced which allow mutagenesis or a sequence change by recombination of DNA sequences. With the help of standard methods z. For example, base substitutions are made, partial sequences are removed, or natural or synthetic sequences are added. For the connection of the DNA fragments with one another adapters or linkers can be attached to the fragments, see, for example, US Pat. Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2 Ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY, or Winnacker "Gene and Clones", VCH Weinheim 2nd edition, 1996
Die Herstellung von Pflanzenzellen mit einer verringerten Aktivität eines Genprodukts kann beispielsweise erzielt werden durch die Expression mindestens einer The production of plant cells having a reduced activity of a gene product can be achieved, for example, by the expression of at least one
entsprechenden antisense-RNA, einer sense-RNA zur Erzielung eines corresponding antisense RNA, a sense RNA to obtain a
Cosuppressionseffekt.es oder die Expression mindestens eines entsprechend konstruierten Ribozyms, das spezifisch Transkripte des obengenannten Genprodukts spaltet. Hierzu können zum einen DNA-Moleküle verwendet werden, die die gesamte codierende Sequenz eines Genprodukts einschließlich eventuell vorhandener flankierender Sequenzen umfassen, als auch DNA-Moleküle, die nur Teile der codierenden Sequenz umfassen, wobei diese Teile lang genug sein müssen, um in den Zellen einen antisense-Effekt zu bewirken. Möglich ist auch die Verwendung von DNA-Sequenzen, die einen hohen Grad an Homologie zu den codiereden Sequenzen eines Genprodukts aufweisen, aber nicht vollkommen identisch sind. Bei der Expression von Nucleinsäuremolekülen in Pflanzen kann das synthetisierte Protein in jedem beliebigen Kompartiment der pflanzlichen Zelle lokalisiert sein. Um aber die Lokalisation in einem bestimmten Kompartiment zu erreichen, kann z. B. die codierende Region mit DNA-Sequenzen verknüpft werden, die die Lokalisierung in einem bestimmten Kompartiment gewährleisten. Derartige Sequenzen sind demCosuppressionseffekt.es or the expression of at least one appropriately engineered ribozyme that specifically cleaves transcripts of the above gene product. For this purpose, DNA molecules may be used which comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules which comprise only parts of the coding sequence, which parts must be long enough to be present in the cells to cause an antisense effect. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but are not completely identical. In the expression of nucleic acid molecules in plants, the synthesized protein may be located in any compartment of the plant cell. But to achieve the localization in a particular compartment, z. For example, the coding region can be linked to DNA sequences that ensure localization in a particular compartment. Such sequences are the
Fachmann bekannt (siehe beispielsweise Braun et al., EMBO J. 1 1 (1992), 3219-3227, Wolter et al., Proc. Natl. Acad. Sei. USA 85 (1988), 846-850, Sonnewald et al., Plant J. 1 (1991 ), 95-106). Die Expression der Nukleinsäuremoleküle kann auch in den See, for example, Braun et al., EMBO J. 1 1 (1992), 3219-3227, Wolter et al., Proc. Natl. Acad., U.S.A. 85 (1988), 846-850, Sonnewald et al. , Plant J. 1 (1991), 95-106). Expression of the nucleic acid molecules can also be found in the
Organellen der Pflanzenzellen stattfinden. Organelles of the plant cells take place.
Die transgenen Pflanzenzellen können nach bekannten Techniken zu ganzen Pflanzen regeneriert werden. Bei den transgenen Pflanzen kann es sich prinzipiell um Pflanzen jeder beliebigen Pflanzenspezies handeln, d.h., sowohl monokotyle als auch dikotyle Pflanzen. The transgenic plant cells can be regenerated to whole plants by known techniques. The transgenic plants may, in principle, be plants of any plant species, that is, both monocotyledonous and dicotyledonous plants.
So sind transgene Pflanzen erhältlich, die veränderte Eigenschaften durch Thus, transgenic plants are available, the altered properties by
Überexpression, Suppression oder Inhibierung homologer (= natürlicher) Gene oder Gensequenzen oder Expression heterologer (= fremder) Gene oder Gensequenzen aufweisen. Overexpression, suppression or inhibition of homologous (= natural) genes or gene sequences or expression of heterologous (= foreign) genes or gene sequences.
Vorzugsweise können die erfindungsgemäßen Verbindungen in transgenen Kulturen eingesetzt werden, welche gegen Wuchsstoffe, wie z. B. Dicamba oder gegen Preferably, the compounds of the invention can be used in transgenic cultures which are resistant to growth factors, such as. B. Dicamba or against
Herbizide, die essentielle Pflanzenenzyme, z. B. Acetolactatsynthasen (ALS), EPSP Synthasen, Glutaminsynthasen (GS) oder Hydroxyphenylpyruvat Dioxygenasen (HPPD) hemmen, respektive gegen Herbizide aus der Gruppe der Sulfonylharnstoffe, der Glyphosate, Glufosinate oder Benzoylisoxazole und analogen Wirkstoffe, resistent sind. Herbicides containing essential plant enzymes, e.g. As acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or Hydroxyphenylpyruvat dioxygenases (HPPD) inhibit or herbicides from the group of sulfonylureas, the glyphosate, glufosinate or benzoylisoxazole and analogues, resistant.
Bei der Anwendung der erfindungsgemäßen Wirkstoffe in transgenen Kulturen treten neben den in anderen Kulturen zu beobachtenden Wirkungen gegenüber In the application of the active compounds according to the invention in transgenic cultures, in addition to the effects to be observed in other cultures
Schadpflanzen oftmals Wirkungen auf, die für die Applikation in der jeweiligen transgenen Kultur spezifisch sind, beispielsweise ein verändertes oder speziell erweitertes Unkrautspektrum, das bekämpft werden kann, veränderte  Harmful plants often have effects that are specific for application in the particular transgenic culture, such as altered or specially extended weed spectrum that can be controlled
Aufwandmengen, die für die Applikation eingesetzt werden können, vorzugsweise gute Kombinierbarkeit mit den Herbiziden, gegenüber denen die transgene Kultur resistent ist, sowie Beeinflussung von Wuchs und Ertrag der transgenen Kulturpflanzen. Application rates that can be used for the application, preferably good Combinability with the herbicides to which the transgenic culture is resistant, as well as influencing the growth and yield of the transgenic crops.
Gegenstand der Erfindung ist deshalb auch die Verwendung der erfindungsgemäßen Verbindungen als Herbizide zur Bekämpfung von Schadpflanzen in transgenen The invention therefore also relates to the use of the compounds according to the invention as herbicides for controlling harmful plants in transgenic
Kulturpflanzen. Crops.
Die erfindungsgemäßen Verbindungen können in Form von Spritzpulvern, The compounds of the invention may be in the form of wettable powders,
emulgierbaren Konzentraten, versprühbaren Lösungen, Stäubemitteln oder Granulaten in den üblichen Zubereitungen angewendet werden. Gegenstand der Erfindung sind deshalb auch herbizide und pflanzenwachstumsregulierende Mittel, welche die erfindungsgemäßen Verbindungen enthalten. emulsifiable concentrates, sprayable solutions, dusts or granules are used in the usual preparations. The invention therefore also relates to herbicidal and plant growth-regulating agents which contain the compounds according to the invention.
Die erfindungsgemäßen Verbindungen können auf verschiedene Art formuliert werden, je nachdem welche biologischen und/oder chemisch-physikalischen Parameter vorgegeben sind. Als Formulierungsmöglichkeiten kommen beispielsweise in Frage: Spritzpulver (WP), wasserlösliche Pulver (SP), wasserlösliche Konzentrate, The compounds according to the invention can be formulated in various ways, depending on which biological and / or chemical-physical parameters are predetermined. Possible formulation options are, for example: wettable powder (WP), water-soluble powders (SP), water-soluble concentrates,
emulgierbare Konzentrate (EC), Emulsionen (EW), wie Öl-in-Wasser- und emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and
Wasser-in-ÖI-Emulsionen, versprühbare Lösungen, Suspensionskonzentrate (SC), Dispersionen auf Öl- oder Wasserbasis, ölmischbare Lösungen, Kapselsuspensionen (CS), Stäubemittel (DP), Beizmittel, Granulate für die Streu- und Bodenapplikation, Granulate (GR) in Form von Mikro-, Sprüh-, Aufzugs- und Adsorptionsgranulaten, wasserdispergierbare Granulate (WG), wasserlösliche Granulate (SG), Water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), oil- or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusts (DP), mordants, granules for spreading and soil application, granules (GR) in the form of micro, spray, elevator and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG),
ULV-Formulierungen, Mikrokapseln und Wachse. ULV formulations, microcapsules and waxes.
Diese einzelnen Formulierungstypen sind im Prinzip bekannt und werden These individual formulation types are known and will be known in principle
beispielsweise beschrieben in: Winnacker-Küchler, "Chemische Technologie", for example, described in: Winnacker-Kuchler, "Chemical Technology",
Band 7, C. Hanser Verlag München, 4. Aufl. 1986, Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, N.Y., 1973, K. Martens, "Spray Drying" Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London. Volume 7, C. Hanser Verlag Munich, 4th ed. 1986, Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, N.Y., 1973, K. Martens, "Spray Drying" Handbook, 3rd ed. 1979, G. Goodwin Ltd. London.
Die notwendigen Formulierungshilfsmittel wie Inertmaterialien, Tenside, Lösungsmittel und weitere Zusatzstoffe sind ebenfalls bekannt und werden beispielsweise The necessary formulation auxiliaries such as inert materials, surfactants, solvents and other additives are also known and are, for example
beschrieben in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell N.J., H.v. Olphen, "Introduction to Clay Colloid Chemistry", 2nd Ed., J. Wiley & Sons, N.Y., C. Marsden, "Solvents Guide", 2nd Ed., Interscience, N.Y. 1963, McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J., Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964, Schönfeldt, "Grenzflächenaktive described in Watkins, "Handbook of Insecticide Dust Diluents and Carriers," 2nd Ed., Darland Books, Caldwell NJ, Hv Olphen, "Introduction to Clay Colloid Chemistry, 2nd Ed., J. Wiley & Sons, NY, C. Marsden, "Solvents Guide", 2nd Ed., Interscience, NY 1963, McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood NJ, Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., NY 1964, Schonfeldt, "Surface Active
Äthylenoxidaddukte", Wiss. Verlagsgesell., Stuttgart 1976, Winnacker-Küchler, "Chemische Technologie", Band 7, C. Hanser Verlag München, 4. Aufl. 1986. Äthylenoxidaddukte ", Wiss. Verlagsgesell., Stuttgart 1976, Winnacker-Küchler," Chemical Technology ", Volume 7, C. Hanser Verlag Munich, 4th ed. 1986.
Auf der Basis dieser Formulierungen lassen sich auch Kombinationen mit anderen Pestizid wirksamen Stoffen, wie z.B. Insektiziden, Akariziden, Herbiziden, Fungiziden, sowie mit Safenern, Düngemitteln und/oder Wachstumsregulatoren herstellen, z.B. in Form einer Fertigformulierung oder als Tankmix. Geeignete Safener sind On the basis of these formulations, combinations with other pesticidally active substances, such as e.g. Insecticides, acaricides, herbicides, fungicides, as well as with safeners, fertilizers and / or growth regulators, e.g. in the form of a ready-made formulation or as a tank mix. Suitable safeners are
beispielsweise Mefenpyr-diethyl, Cyprosulfamid, Isoxadifen-ethyl, Cloquintocet-mexyl und Dichlormid. Spritzpulver sind in Wasser gleichmäßig dispergierbare Präparate, die neben dem Wirkstoff außer einem Verdünnungs- oder Inertstoff noch Tenside ionischer und/oder nichtionischer Art (Netzmittel, Dispergiermittel), z.B. polyoxyethylierte Alkylphenole, polyoxethylierte Fettalkohole, polyoxethylierte Fettamine, Fettalkoholpolyglykol- ethersulfate, Alkansulfonate, Alkylbenzolsulfonate, ligninsulfonsaures Natrium, for example, mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl, cloquintocet-mexyl and dichloromide. Injectable powders are preparations which are uniformly dispersible in water and contain surfactants of the ionic and / or nonionic type (wetting agents, dispersants) in addition to the active ingredient except a diluent or inert substance. polyoxyethylated alkylphenols, polyoxethylated fatty alcohols, polyoxethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate,
2,2'-dinaphthylmethan-6,6'-disulfonsaures Natrium, dibutylnaphthalin-sulfonsaures Natrium oder auch oleoylmethyltaurinsaures Natrium enthalten. Zur Herstellung der Spritzpulver werden die herbiziden Wirkstoffe beispielsweise in üblichen Apparaturen wie Hammermühlen, Gebläsemühlen und Luftstrahlmühlen feingemahlen und gleichzeitig oder anschließend mit den Formulierungshilfsmitteln vermischt. 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, dibutylnaphthalene-sulfonic acid sodium or oleoylmethyltaurine acid. To prepare the wettable powders, the herbicidal active compounds are finely ground, for example, in customary apparatus such as hammer mills, blower mills and air-jet mills and mixed simultaneously or subsequently with the formulation auxiliaries.
Emulgierbare Konzentrate werden durch Auflösen des Wirkstoffes in einem Emulsifiable concentrates are made by dissolving the active ingredient in one
organischen Lösungsmittel z.B. Butanol, Cyclohexanon, Dimethylformamid, Xylol oder auch höhersiedenden Aromaten oder Kohlenwasserstoffen oder Mischungen der organischen Lösungsmittel unter Zusatz von einem oder mehreren Tensiden ionischer und/oder nichtionischer Art (Emulgatoren) hergestellt. Als Emulgatoren können beispielsweise verwendet werden: Alkylarylsulfonsaure Calzium-Salze wie organic solvents e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents with the addition of one or more surfactants of ionic and / or nonionic type (emulsifiers). Examples of emulsifiers which may be used are: alkylarylsulfonic acid calcium salts, such as
Ca-Dodecylbenzolsulfonat oder nichtionische Emulgatoren wie Ca-dodecylbenzenesulfonate or nonionic emulsifiers such as
Fettsäurepolyglykolester, Alkylarylpolyglykolether, Fettalkoholpolyglykolether, Fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers,
Propylenoxid-Ethylenoxid-Kondensationsprodukte, Alkylpolyether, Sorbitanester wie z.B. Sorbitanfettsäureester oder Polyoxethylensorbitanester wie z.B. Propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as For example, sorbitan fatty acid esters or Polyoxethylenensorbitanester such as
Polyoxyethylensorbitanfettsäureester. Polyoxyethylene.
Stäubemittel erhält man durch Vermählen des Wirkstoffes mit fein verteilten festen Stoffen, z.B. Talkum, natürlichen Tonen, wie Kaolin, Bentonit und Pyrophyllit, oder Diatomeenerde. Dusts are obtained by milling the active ingredient with finely divided solids, e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
Suspensionskonzentrate können auf Wasser- oder Ölbasis sein. Sie können beispielsweise durch Naß-Vermahlung mittels handelsüblicher Perlmühlen und gegebenenfalls Zusatz von Tensiden, wie sie z.B. oben bei den anderen Suspension concentrates may be water or oil based. They can be prepared, for example, by wet grinding using commercially available bead mills and, if appropriate, addition of surfactants, as described, for example, in US Pat. upstairs with the others
Formulierungstypen bereits aufgeführt sind, hergestellt werden. Formulation types already listed are produced.
Emulsionen, z.B. ÖI-in-Wasser-Emulsionen (EW), lassen sich beispielsweise mittels Rührern, Kolloidmühlen und/oder statischen Mischern unter Verwendung von wäßrigen organischen Lösungsmitteln und gegebenenfalls Tensiden, wie sie z.B. oben bei den anderen Formulierungstypen bereits aufgeführt sind, herstellen. Emulsions, e.g. Oil-in-water emulsions (EW) can be prepared, for example, by means of stirrers, colloid mills and / or static mixers using aqueous organic solvents and optionally surfactants, as described e.g. listed above for the other formulation types.
Granulate können entweder durch Verdüsen des Wirkstoffes auf adsorptionsfähiges, granuliertes Inertmaterial hergestellt werden oder durch Aufbringen von Granules can be prepared either by spraying the active ingredient on adsorptive, granulated inert material or by applying
Wirkstoffkonzentraten mittels Klebemitteln, z.B. Polyvinylalkohol, polyacrylsaurem Natrium oder auch Mineralölen, auf die Oberfläche von Trägerstoffen wie Sand, Kaolinite oder von granuliertem Inertmaterial. Auch können geeignete Wirkstoffe in der für die Herstellung von Düngemittelgranulaten üblichen Weise - gewünschtenfalls in Mischung mit Düngemitteln - granuliert werden. Active substance concentrates by means of adhesives, e.g. Polyvinyl alcohol, polyacrylic acid sodium or mineral oils, on the surface of carriers such as sand, kaolinites or granulated inert material. It is also possible to granulate suitable active ingredients in the manner customary for the production of fertilizer granules, if desired in admixture with fertilizers.
Wasserdispergierbare Granulate werden in der Regel nach den üblichen Verfahren wie Sprühtrocknung, Wirbelbett-Granulierung, Teller-Granulierung, Mischung mit Hochgeschwindigkeitsmischern und Extrusion ohne festes Inertmaterial hergestellt. Zur Herstellung von Teller-, Fließbett-, Extruder- und Sprühgranulate siehe z.B. Water-dispersible granules are generally prepared by the usual methods such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material. For the preparation of plate, fluid bed, extruder and spray granules, see e.g.
Verfahren in "Spray-Drying Handbook" 3rd ed. 1979, G. Goodwin Ltd., London, J.E. Browning, "Agglomeration", Chemical and Engineering 1967, Seiten 147 ff, "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York 1973, S. 8-57. Für weitere Einzelheiten zur Formulierung von Pflanzenschutzmitteln siehe z.B. G.C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961 , Seiten 81 -96 und J.D. Freyer, S.A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, Seiten 101 -103. Process in "Spray-Drying Handbook" 3rd Ed. 1979, G. Goodwin Ltd., London, JE Browning, "Agglomeration", Chemical and Engineering 1967, pages 147 et seq., "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw. Hill, New York 1973, pp. 8-57. See, for example, GC Klingman, "Weed Control as a Science," John Wiley and Sons, Inc., New York, 1961, pp. 81-96, and JD Freyer, SA Evans, "Weed Control Handbook," for further details on pesticide formulation. 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.
Die agrochemischen Zubereitungen enthalten in der Regel 0.1 bis 99 Gew.-%, insbesondere 0.1 bis 95 Gew.-%, erfindungsgemäße Verbindungen. The agrochemical preparations generally contain from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of compounds according to the invention.
In Spritzpulvern beträgt die Wirkstoffkonzentration z.B. etwa 10 bis 90 Gew.-%, der Rest zu 100 Gew.-% besteht aus üblichen Formulierungsbestandteilen. Bei emulgierbaren Konzentraten kann die Wirkstoffkonzentration etwa 1 bis 90, vorzugsweise 5 bis 80 Gew.-% betragen. Staubförmige Formulierungen enthalten 1 bis 30 Gew.-% Wirkstoff, vorzugsweise meistens 5 bis 20 Gew.-% an Wirkstoff, versprühbare Lösungen enthalten etwa 0.05 bis 80, vorzugsweise 2 bis 50 Gew.-% Wirkstoff. Bei wasserdispergierbaren Granulaten hängt der Wirkstoffgehalt zum Teil davon ab, ob die wirksame Verbindung flüssig oder fest vorliegt und welche In wettable powders, the drug concentration is e.g. about 10 to 90 wt .-%, the balance to 100 wt .-% consists of conventional formulation ingredients. For emulsifiable concentrates, the active ingredient concentration may be about 1 to 90, preferably 5 to 80 wt .-%. Dust-like formulations contain 1 to 30 wt .-% of active ingredient, preferably usually 5 to 20 wt .-% of active ingredient, sprayable solutions contain about 0.05 to 80, preferably 2 to 50 wt .-% of active ingredient. In the case of water-dispersible granules, the active ingredient content depends, in part, on whether the active compound is liquid or solid and which
Granulierhilfsmittel, Füllstoffe usw. verwendet werden. Bei den in Wasser Granulation aids, fillers, etc. are used. In the water
dispergierbaren Granulaten liegt der Gehalt an Wirkstoff beispielsweise zwischen 1 und 95 Gew.-%, vorzugsweise zwischen 10 und 80 Gew.-%. Daneben enthalten die genannten Wirkstofformulierungen gegebenenfalls die jeweils üblichen Haft-, Netz-, Dispergier-, Emulgier-, Penetrations-, Konservierungs-, dispersible granules, the content of active ingredient is for example between 1 and 95 wt .-%, preferably between 10 and 80 wt .-%. In addition, the active substance formulations mentioned optionally contain the customary adhesive, wetting, dispersing, emulsifying, penetrating, preserving,
Frostschutz- und Lösungsmittel, Füll-, Träger- und Farbstoffe, Entschäumer, Antifreeze and solvents, fillers, carriers and dyes, defoamers,
Verdunstungshemmer und den pH-Wert und die Viskosität beeinflussende Mittel. Auf der Basis dieser Formulierungen lassen sich auch Kombinationen mit anderen Pestizid wirksamen Stoffen, wie z.B. Insektiziden, Akariziden, Herbiziden, Fungiziden, sowie mit Safenern, Düngemitteln und/oder Wachstumsregulatoren herstellen, z.B. in Form einer Fertigformulierung oder als Tankmix. Zur Anwendung werden die in handelsüblicher Form vorliegenden Formulierungen gegebenenfalls in üblicher Weise verdünnt z.B. bei Spritzpulvern, emulgierbaren Konzentraten, Dispersionen und wasserdispergierbaren Granulaten mittels Wasser. Staubförmige Zubereitungen, Boden- bzw. Streugranulate sowie versprühbare Lösungen werden vor der Anwendung üblicherweise nicht mehr mit weiteren inerten Stoffen verdünnt. Evaporation inhibitors and pH and viscosity affecting agents. On the basis of these formulations, it is also possible to prepare combinations with other pesticide-active substances, such as, for example, insecticides, acaricides, herbicides, fungicides, and with safeners, fertilizers and / or growth regulators, for example in the form of a ready-to-use formulation or as a tank mix. For use, the formulations present in commercially available form are optionally diluted in customary manner, for example in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules by means of water. Dust-like preparations, ground or scattered granules and sprayable solutions are usually no longer before use with other inert Diluted substances.
Mit den äußeren Bedingungen wie Temperatur, Feuchtigkeit, der Art des verwendeten Herbizids, u.a. variiert die erforderliche Aufwandmenge der Verbindungen der Formel (I). Sie kann innerhalb weiter Grenzen schwanken, z.B. zwischen 0,001 und 1 ,0 kg/ha oder mehr Aktivsubstanz, vorzugsweise liegt sie jedoch zwischen 0,005 und 750 g/ha. With the external conditions such as temperature, humidity, the type of herbicide used, u.a. varies the required application rate of the compounds of formula (I). It can vary within wide limits, e.g. between 0.001 and 1.0 kg / ha or more of active substance, but is preferably between 0.005 and 750 g / ha.
Die nachstehenden Beispiele erläutern die Erfindung. A. Chemische Beispiele The following examples illustrate the invention. A. Chemical examples
1 . Synthese von 6-Chlor-4-phenyl-5-(3,5-difluorphenyl)-N-(1 -methyltetrazol-5-yl)- pyrazin-3-on-2-carbonsäureamid, (Tabellenbeispiel Nr. 1 -6)  1 . Synthesis of 6-chloro-4-phenyl-5- (3,5-difluorophenyl) -N- (1-methyltetrazol-5-yl) -pyrazine-3-one-2-carboxylic acid amide, (Table Example No. 1-6)
Zu 327 mg (1 mmol) 6-Chlor-4-phenyl-5-(3,5-difluorphenyl)-pyrazin-3-on-2- carbonsäure und 152 mg (1 .5 mmol) 1 -Methyl-5-aminotetrazol in 3 ml Pyridin werden bei 0°C 157 mg (1 .3 mmol) Thionylchlorid gegeben. Das Gemisch wird 16h beiTo 327 mg (1 mmol) of 6-chloro-4-phenyl-5- (3,5-difluorophenyl) -pyrazine-3-one-2-carboxylic acid and 152 mg (1 .5 mmol) of 1-methyl-5-aminotetrazole in 3 ml of pyridine are added at 0 ° C 157 mg (1 .3 mmol) of thionyl chloride. The mixture is 16h
Raumtemperatur gerührt. Anschließend wird mit 2N Salzsäure versetzt, das Produkt abgesaugt und mit Wasser gewaschen. Ausbeute 309 mg (70 %). Room temperature stirred. Then 2N hydrochloric acid is added, the product is filtered off with suction and washed with water. Yield 309 mg (70%).
Die in nachfolgenden Tabellen aufgeführten Beispiele wurden analog oben genannten Methoden hergestellt beziehungsweise sind analog oben genannten Methoden erhältlich. Diese Verbindungen sind ganz besonders bevorzugt. The examples listed in the following tables were prepared analogously to the above-mentioned methods or are obtainable analogously to the methods mentioned above. These compounds are most preferred.
Die verwendeten Abkürzungen bedeuten: Ph = Phenyl Me = Methyl The abbreviations used mean: Ph = phenyl Me = methyl
Tabelle 1 : Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q1, R3für Methyl, worin X1 für CR2a und X2 für CR2b stehen, und Y Sauerstoff bedeutet. Table 1: Compounds of the invention of the general formula (I) wherein Q is Q 1 , R 3 is methyl, wherein X 1 is CR 2a and X 2 is CR 2b , and Y is oxygen.
Figure imgf000033_0001
Figure imgf000033_0001
Physikalische Daten Physical data
Nr. R1 R2a R2b No. R 1 R 2a R 2b
(Ή-NMR, DMSO-de, 400 MHz) (Ή-NMR, DMSO-de, 400 MHz)
1-1 Me Ph Cl 1-1 Me Ph Cl
1-2 Me 3,5-F2Ph Cl 1-2M 3,5-F 2 Ph Cl
1-3 MeOC2H4 Ph Cl 1-3 MeOC 2 H 4 Ph Cl
1-4 MeOC2H4 3,5-F2Ph Cl1-4 MeOC 2 H 4 3,5-F 2 Ph Cl
.98 (brs,1 H), 7.52-7.28 (m,6H), 7.18-7.15 .98 (brs, 1 H), 7.52-7.28 (m, 6H), 7.18-7.15
1-5 Ph Ph 11 1-5 Ph Ph 11
Cl  Cl
(m,2H), 7.07-7.04 (m,2H), 3.97 (s,3H)  (m, 2H), 7.07-7.04 (m, 2H), 3.97 (s, 3H)
1-6 Ph 3,5-F2Ph Cl 11.79 (brs,1 H), 7.41-7.19 (m,8H), 3.95 (s,3H)1-6 Ph 3,5-F 2 Ph Cl 11:79 (brs, 1H), 7.41-7.19 (m, 8H), 3.95 (s, 3H)
1-7 2-MePh Ph Cl 1-7 2-MePh Ph Cl
1-8 2-MePh 3,5-F2Ph Cl 1-8 2-MePh 3,5-F 2 Ph Cl
1-9 3-MePh Ph Cl  1-9 3-Meph Ph Cl
1-10 3-MePh 3,5-F2Ph Cl 1-10 3-MePh 3,5-F 2 Ph Cl
1-1 1 4-MePh Ph Cl  1-1 1 4-MePh Ph Cl
1-12 4-MePh 3,5-F2Ph Cl 1-12 4-MePh 3,5-F 2 Ph Cl
1-13 2-MeOPh Ph Cl  1-13 2-MeOPh Ph Cl
1-14 2-MeOPh 3,5-F2Ph Cl 1-14 2-MeOH 3,5-F 2 Ph Cl
1-15 3-MeOPh Ph Cl  1-15 3-MeOPh Ph Cl
1-16 3-MeOPh 3,5-F2Ph Cl 1-16 3-MeOPh 3,5-F 2 Ph Cl
1-17 4-MeOPh Ph Cl  1-17 4-MeOPh Ph Cl
1-18 4-MeOPh 3,5-F2Ph Cl 1-18 4-MeOPh 3,5-F 2 Ph Cl
1-19 4-FPh Ph Cl  1-19 4-FPh Ph Cl
1-20 4-FPh 3,5-F2Ph Cl  1-20 4-FPh 3.5-F2Ph Cl
1-21 4-CIPh Ph Cl  1-21 4-CIPh Ph Cl
1-22 4-CIPh 3,5-F2Ph Cl  1-22 4-CIPh 3,5-F2Ph Cl
Ph 12.12 (brs,1 H), 7.97 (s,1 H), 7.43-7.30 (m,6H), 7.28- Ph 12.12 (brs, 1H), 7.97 (s, 1H), 7.43-7.30 (m, 6H), 7.28-
1-23 Ph H 1-23 Ph H
7.13 (m,4H), 3.96 (s,3H)  7.13 (m, 4H), 3.96 (s, 3H)
1-24 Ph 3,5-F2Ph H 1-24 Ph 3,5-F 2 Ph H
1-25 4-MeOPh Ph H -26 4-MeOPh 3,5-F2Ph H1-25 4-MeOPh Ph H -26 4-MeOPh 3,5-F 2 Ph H
-27 4-FPh Ph H-27 4-FPh Ph H
-28 4-FPh 3,5-F2Ph H-28 4-FPh 3.5-F2Ph H
-29 Ph Ph Me-29 Ph Ph Me
-30 Ph 3,5-F2Ph Me-30 Ph 3,5-F 2 Ph Me
-31 4-MeOPh Ph Me-31 4-MeOPh Ph Me
-32 4-MeOPh 3,5-F2Ph Me-32 4-MeOPh 3,5-F 2 Ph Me
-33 4-FPh Ph Me-33 4-FPh Ph Me
-34 4-FPh 3,5-F2Ph Me -34 4-FPh 3.5-F2Ph Me
Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q1, R3 für Methyl, X1 für CR2a und X2 für N steht, und Y Sauerstoff bedeutet. Compounds of the invention of the general formula (I) wherein Q is Q 1 , R 3 is methyl, X 1 is CR 2a and X 2 is N, and Y is oxygen.
Figure imgf000034_0001
Figure imgf000034_0001
Nr. R1 R2a Physikalische Daten No. R 1 R2a Physical data
( H-NMR, DMSO-d6, 400 MHz) (H-NMR, DMSO-d 6 , 400 MHz)
12.07 (brs,1 H), 7.76 (m,2H), 7.69-7.59 (m,3H), 3.97 (s,3H), 12.07 (brs, 1H), 7.76 (m, 2H), 7.69-7.59 (m, 3H), 3.97 (s, 3H),
2-1 Me Ph 2-1 Me Ph
3.85 (s,3H)  3.85 (s, 3H)
2-2 Me 3,5-F2Ph 12.00 (brs,1 H), 7.61 (m,1 H), 7.54 (m,2H), 3.96 (s,3H), 3.83 2-2 Me 3,5-F 2 Ph 12.00 (brs, 1H), 7.61 (m, 1H), 7.54 (m, 2H), 3.96 (s, 3H), 3.83
(s,3H)  (S, 3H)
12.01 (brs,1 H), 7.72 (m,2H), 7.66-7.55 (m,3H), 4.28 (m,2H), 12.01 (brs, 1H), 7.72 (m, 2H), 7.66-7.55 (m, 3H), 4.28 (m, 2H),
2-3 MeOC2H4 Ph 2-3 MeOC 2 H 4 Ph
3.98 (s,3H), 3.64 (m,2H), 3.12 (s,3H)  3.98 (s, 3H), 3.64 (m, 2H), 3.12 (s, 3H)
2-4 H), 7.60 (m,1 H), 7.51 (m,2H), 4.24 (m,2H),  2-4 H), 7.60 (m, 1H), 7.51 (m, 2H), 4.24 (m, 2H),
MeOC2H4 3,5-F2Ph 11.98 (brs,1 3.97 MeOC 2 H 4 3,5-F 2 Ph 11.98 (brs, 1 3.97
(s,3H), 3.64 (m,2H), 3.17 (s,3H)  (s, 3H), 3.64 (m, 2H), 3.17 (s, 3H)
Hydrat: 13.37 (brs,1 H), 11.22 (brs,1 H), 10.99 (brs,1 H), 7.92- Hydrate: 13.37 (brs, 1H), 11.22 (brs, 1H), 10.99 (brs, 1H), 7.92-
2-5 Ph Ph 2-5 Ph Ph
7.18 (m,10H), 3.99 (s,3H)  7.18 (m, 10H), 3.99 (s, 3H)
9.41 (brs,1 H), 7.65- 9.41 (brs, 1H), 7.65-
2-6 Ph 3,5-F2Ph Hydrat: 14.62 (brs,1 H), 13.09 (brs,1 H), 2-6 Ph 3,5-F 2 Ph hydrate: 14.62 (brs, 1H), 13.09 (brs, 1H),
7.11 (m,8H), 3.98 (s,3H)  7.11 (m, 8H), 3.98 (s, 3H)
2-7 4-MePh Ph  2-7 4-Meph Ph
2-8 4-MePh 3,5-F2Ph 2-8 4-MePh 3,5-F 2 Ph
Hydrat: 14.63 (brs,1 H), 13.23 (brs,1 H), 9.33 (brs,1 H), 7.55- Hydrate: 14.63 (brs, 1H), 13.23 (brs, 1H), 9.33 (brs, 1H), 7.55-
2-9 4-MeOPh Ph 7.50 (m,4H), 7.13 (m,1 H), 6.96 (m,2H), 3.99 (s,3H), 3.74 2-9 4-MeOPh Ph 7.50 (m, 4H), 7.13 (m, 1H), 6.96 (m, 2H), 3.99 (s, 3H), 3.74
(s,3H)  (S, 3H)
Hydrat: 14.58 (brs,1 H), 11.46 (brs,1 H), 11.13 (brs,1 H), 8.34 Hydrate: 14.58 (brs, 1H), 11.46 (brs, 1H), 11.13 (brs, 1H), 8.34
2-10 4-MeOPh 3,5-F2Ph (d,1 H), 7.72-7.58 (m,3H), 7.19 (t,1 H), 7.13 (d,1 H), 7.02 2-10 4-MeOPh 3,5-F 2 Ph (d, 1H), 7.72-7.58 (m, 3H), 7.19 (t, 1H), 7.13 (d, 1H), 7.02
(t,1 H), 3.98 (s,3H), 3.87 (s,3H) Hydrat: 14.91 (brs,1H), 11.59 (brs,1H), 11.12 (brs,1H), 8.35-11 2-MeOPh Ph (d,1H), 7.96 (d,2H), 7.75 (t,1H), 7.76 (t,2H), 7.19 (t,1H), 7.13 (t, 1H), 3.98 (s, 3H), 3.87 (s, 3H) Hydrate: 14.91 (brs, 1H), 11.59 (brs, 1H), 11.12 (brs, 1H), 8.35-11 2-MeOPh Ph (d, 1H), 7.96 (d, 2H), 7.75 (t, 1H), 7.76 (t, 2H), 7.19 (t, 1H), 7.13
(d,1H), 7.02 (t,1H), 3.99 (s,3H), 3.87 (s,3H)  (d, 1H), 7.02 (t, 1H), 3.99 (s, 3H), 3.87 (s, 3H)
Hydrat: 14.58 (brs,1H), 11.46 (brs,1H), 11.13 (brs,1H), 8.34-12 2-MeOPh 3,5-F2Ph (d,1H), 7.72-7.58 (m,3H), 7.19 (t,1H), 7.13 (d,1H), 7.02 Hydrate: 14.58 (brs, 1H), 11.46 (brs, 1H), 11.13 (brs, 1H), 8.34-12 2-MeOPh 3,5-F 2 Ph (d, 1H), 7.72-7.58 (m, 3H) , 7.19 (t, 1H), 7.13 (d, 1H), 7.02
(t,1H), 3.98 (s,3H), 3.87 (s,3H)  (t, 1H), 3.98 (s, 3H), 3.87 (s, 3H)
3,4- Hydrat: 14.66 (brs,1H), 13.15 (brs,1H), 9.42 (brs,1H), 8.01-13 Ph  3,4-hydrate: 14.66 (brs, 1H), 13.15 (brs, 1H), 9.42 (brs, 1H), 8.01-13 Ph
(OCH20)Ph (d,2H), 7.68 (t,1H), 7.57 (t,2H), 7.30 (d,1H), 6.99 (dd,1H), (OCH 2 O) Ph (d, 2H), 7.68 (t, 1H), 7.57 (t, 2H), 7.30 (d, 1H), 6.99 (dd, 1H),
6.83 (d,1H), 6.02 (s,2H), 3.99 (s,3H)  6.83 (d, 1H), 6.02 (s, 2H), 3.99 (s, 3H)
3,4- Hydrat: 13.30 (brs,1H), 11.23 (brs,1H), 10.84 (brs,1H), 7.63--14 3,5-F2Ph 3,4-hydrate: 13.30 (brs, 1H), 11.23 (brs, 1H), 10.84 (brs, 1H), 7.63--14 3,5-F 2 Ph
(OCH20)Ph 7.50 (m,3H), 7.38 (d,1H), 7.08 (dd,1H), 6.94 (d,1H), 6.04 (OCH 2 O) Ph 7.50 (m, 3H), 7.38 (d, 1H), 7.08 (dd, 1H), 6.94 (d, 1H), 6.04
(s,2H), 3.97 (s,3H) (s, 2H), 3.97 (s, 3H)
-15 4-FPh Ph-15 4-FPh Ph
-16 4-FPh 3,5-F2Ph -16 4-FPh 3,5-F 2 Ph
Formulierungsbeispiele formulation Examples
Ein Stäubemittel wird erhalten, indem man 10 Gew.-Teile einer Verbindung der Formel (I) und/oder deren Salze und 90 Gew.-Teile Talkum als Inertstoff mischt und in einer Schlagmühle zerkleinert.  A dust is obtained by mixing 10 parts by weight of a compound of formula (I) and / or salts thereof and 90 parts by weight of talc as an inert material and comminuting in a hammer mill.
Ein in Wasser leicht dispergierbares, benetzbares Pulver wird erhalten, indem man 25 Gewichtsteile einer Verbindung der Formel (I) und/oder deren Salze, 64 Gew.-Teile kaolinhaltigen Quarz als Inertstoff, 10 Gewichtsteile A wettable powder easily dispersible in water is obtained by adding 25 parts by weight of a compound of formula (I) and / or its salts, 64 parts by weight of kaolin-containing quartz as inert material, 10 parts by weight
ligninsulfonsaures Kalium und 1 Gew.-Teil oleoylmethyltaurinsaures Natrium als Netz- und Dispergiermittel mischt und in einer Stiftmühle mahlt.  potassium lignosulfonate and 1 part by weight oleoylmethyltaurine sodium as wetting and dispersing agent and grinding in a pin mill.
Ein in Wasser leicht dispergierbares Dispersionskonzentrat wird erhalten, indem man 20 Gew.-Teile einer Verbindung der Formel (I) und/oder deren Salze mit 6 Gew.-Teilen Alkylphenolpolyglykolether (©Triton X 207), 3 Gew.-Teilen A dispersion concentrate readily dispersible in water is obtained by reacting 20 parts by weight of a compound of the formula (I) and / or salts thereof with 6 parts by weight of alkylphenol polyglycol ether (© Triton X 207), 3 parts by weight
Isotridecanolpolyglykolether (8 EO) und 71 Gew.-Teilen paraffinischem  Isotridecanol polyglycol ether (8 EO) and 71 parts by weight paraffinic
Mineralöl (Siedebereich z.B. ca.255 bis über 277 C) mischt und in einer Reibkugelmühle auf eine Feinheit von unter 5 Mikron vermahlt.  Mineral oil (boiling range, for example, about 255 to about 277 C) mixed and ground in a ball mill to a fineness of less than 5 microns.
Ein emulgierbares Konzentrat wird erhalten aus 15 Gew.-Teilen einer An emulsifiable concentrate is obtained from 15 parts by weight of a
Verbindung der Formel (I) und/oder deren Salze, 75 Gew.-Teilen Cyclohexanon als Lösungsmittel und 10 Gew.-Teilen oxethyliertes Nonylphenol als Emulgator.  Compound of the formula (I) and / or salts thereof, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated nonylphenol as emulsifier.
Ein in Wasser dispergierbares Granulat wird erhalten indem man A water-dispersible granules are obtained by
75 Gew.-Teile einer Verbindung der Formel (I) und/oder deren Salze, 10 Gew.-Teile ligninsulfonsaures Calcium, 75 parts by weight of a compound of the formula (I) and / or salts thereof, 10 parts by weight of lignosulfonic acid calcium,
5 Gew.-Teile Natriumlaurylsulfat,  5 parts by weight of sodium lauryl sulfate,
3 Gew.-Teile Polyvinylalkohol und  3 parts by weight of polyvinyl alcohol and
7 Gew.-Teile Kaolin  7 parts by weight kaolin
mischt, auf einer Stiftmühle mahlt und das Pulver in einem Wirbelbett durch mixed, ground on a pin mill and the powder in a fluidized bed by
Aufsprühen von Wasser als Granulierflüssigkeit granuliert. Spraying of water as granulating liquid granulated.
Ein in Wasser dispergierbares Granulat wird auch erhalten, indem man A water-dispersible granule is also obtained by
25 Gew.-Teile einer Verbindung der Formel (I) und/oder deren Salze,  25 parts by weight of a compound of the formula (I) and / or salts thereof,
5 Gew.-Teile 2,2'-dinaphthylmethan-6,6'-disulfonsaures Natrium  5 parts by weight of 2,2'-dinaphthylmethane-6,6'-disulfonate sodium
2 Gew.-Teile oleoylmethyltaurinsaures Natrium,  2 parts by weight oleoylmethyltaurine acid sodium,
1 Gew.-Teil Polyvinylalkohol,  1 part by weight of polyvinyl alcohol,
17 Gew.-Teile Calciumcarbonat und  17 parts by weight of calcium carbonate and
50 Gew.-Teile Wasser  50 parts by weight of water
auf einer Kolloidmühle homogenisiert und vorzerkleinert, anschließend auf einer Perlmühle mahlt und die so erhaltene Suspension in einem Sprühturm mittels einer Einstoffdüse zerstäubt und trocknet.  Homogenized on a colloid mill and pre-crushed, then grinded on a bead mill and the suspension thus obtained in a spray tower by means of a Einstoffdüse atomized and dried.
C. Biologische Beispiele C. Biological examples
1 . Herbizide Wirkung gegen Schadpflanzen im Vorauflauf 1 . Herbicidal action against weevils in pre-emergence
Samen von mono- bzw. dikotylen Unkraut- bzw. Kulturpflanzen werden in  Seeds of monocotyledonous or dicotyledonous weeds are cultivated in
Holzfasertöpfen in sandiger Lehmerde ausgelegt und mit Erde abgedeckt. Die in Form von benetzbaren Pulvern (WP) oder als Emulsionskonzentrate (EC) formulierten erfindungsgemäßen Verbindungen werden dann als wäßrige Suspension bzw. Wood fiber pots laid in sandy loam soil and covered with soil. The compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then used as aqueous suspension or
Emulsion mit einer Wasseraufwandmenge von umgerechnet 600 bis 800 l/ha unter Zusatz von 0,2% Netzmittel auf die Oberfläche der Abdeckerde appliziert. Nach der Behandlung werden die Töpfe im Gewächshaus aufgestellt und unter guten Emulsion with a water application rate of 600 to 800 l / ha with the addition of 0.2% wetting agent applied to the surface of the cover soil. After the treatment, the pots are placed in the greenhouse and under good
Wachstumsbedingungen für die Testpflanzen gehalten. Die visuelle Bonitur der Schäden an den Versuchspflanzen erfolgt nach einer Versuchszeit von 3 Wochen im Vergleich zu unbehandelten Kontrollen (herbizide Wirkung in Prozent (%): 100% Wirkung = Pflanzen sind abgestorben, 0 % Wirkung = wie Kontrollpflanzen). Maintained growth conditions for the test plants. The visual assessment of the damage to the test plants is carried out after a test period of 3 weeks in comparison to untreated controls (herbicidal action in percent (%): 100% effect = plants are dead, 0% effect = like control plants).
Beispielsweise zeigte dabei die Verbindung Nr. 2-1 bei einer Aufwandmenge von 0,32 kg Aktivsubstanz oder weniger pro Hektar eine sehr gute Wirkung (80% bis 100% herbizide Wirkung) gegen Schadpflanzen wie Veronica persica oder Stellaria media. Gleichzeitig lassen erfindungsgemäße Verbindungen Gramineenkulturen wie Gerste, Weizen, Roggen, Hirse, Mais oder Reis im Vorauflaufverfahren selbst bei hohen Wirkstoffdosierungen praktisch ungeschädigt. Einige Substanzen schonen darüber hinaus auch zweikeimblattrige Kulturen wie Soja, Baumwolle, Raps, Zuckerrüben oder Kartoffeln. For example, the compound No. 2-1 at a rate of 0.32 kg of active ingredient or less per hectare showed a very good effect (80% to 100% herbicidal activity) against harmful plants such as Veronica persica or Stellaria media. At the same time, compounds according to the invention leave gramineous crops such as barley, wheat, rye, millet, maize or rice in the pre-emergence process practically undamaged even at high doses of active ingredient. In addition, some substances also protect dicotyledonous crops such as soybeans, cotton, canola, sugar beet or potatoes.
Die erfindungsgemäßen Verbindungen zeigen teilweise eine hohe Selektivität und eignen sich deshalb im Vorauflaufverfahren zur Bekämpfung von unerwünschtem Pflanzenwuchs in landwirtschaftlichen Kulturen. 2. Herbizide Wirkung gegen Schadpflanzen im Nachauflauf  Some of the compounds according to the invention show a high selectivity and are therefore suitable in the pre-emergence process for controlling undesired plant growth in agricultural crops. 2. Herbicidal action against harmful plants in postemergence
Samen von mono- bzw. dikotylen Unkraut- bzw. Kulturpflanzen werden in  Seeds of monocotyledonous or dicotyledonous weeds are cultivated in
Holzfasertöpfen in sandigem Lehmboden ausgelegt, mit Erde abgedeckt und im Gewächshaus unter guten Wachstumsbedingungen angezogen. 2 bis 3 Wochen nach der Aussaat werden die Versuchspflanzen im Einblattstadium behandelt. Die in Form von benetzbaren Pulvern (WP) oder als Emulsionskonzentrate (EC) formulierten erfindungsgemäßen Verbindungen werden dann als wäßrige Suspension bzw. Wood fiber pots laid in sandy loam soil, covered with soil and grown in the greenhouse under good growth conditions. 2 to 3 weeks after sowing, the test plants are treated in the single leaf stage. The compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then used as aqueous suspension or
Emulsion mit einer Wasseraufwandmenge von umgerechnet 600 bis 800 l/ha unter Zusatz von 0,2% Netzmittel auf die grünen Pflanzenteile gesprüht. Nach ca. 3 Wochen Standzeit der Versuchspflanzen im Gewächshaus unter optimalen Emulsion sprayed with an amount of water equivalent of 600 to 800 l / ha with the addition of 0.2% wetting agent on the green plant parts. After about 3 weeks life of the test plants in the greenhouse under optimal
Wachstumsbedingungen wird die Wirkung der Präparate visuell im Vergleich zu unbehandelten Kontrollen bonitiert (herbizide Wirkung in Prozent (%): 100% Wirkung = Pflanzen sind abgestorben, 0 % Wirkung = wie Kontrollpflanzen). Beispielsweise zeigten dabei die Verbindungen Nr. 2-1 und 2-2 bei einer Aufwandmenge von 0,32 kg Aktivsubstanz oder weniger pro Hektar eine sehr gute herbizide Wirkung (80% bis 100% herbizide Wirkung) gegen Schadpflanzen wie Veronica persica und Stellaria media. Gleichzeitig lassen erfindungsgemäße Verbindungen Gramineenkulturen wie Gerste, Weizen, Roggen, Hirse, Mais oder Reis im Nachauflaufverfahren selbst bei hohen Wirkstoffdosierungen praktisch ungeschädigt. Einige Substanzen schonen darüber hinaus auch zweikeimblättrige Kulturen wie Soja, Baumwolle, Raps, Growth conditions, the effect of the preparations is scored visually compared to untreated controls (herbicidal action in percent (%): 100% effect = plants are dead, 0% effect = like control plants). For example, compounds Nos. 2-1 and 2-2 exhibited a very good herbicidal activity (80% to 100% herbicidal activity) against harmful plants such as Veronica persica and Stellaria media at an application rate of 0.32 kg of active substance or less per hectare. At the same time, compounds according to the invention leave gramineous crops such as barley, wheat, rye, millet, maize or rice, post-emergence, virtually undamaged, even at high doses of active ingredient. In addition, some substances also protect dicotyledonous crops such as soya, cotton, rapeseed,
Zuckerrüben oder Kartoffeln. Die erfindungsgemäßen Verbindungen zeigen teilweise eine hohe Selektivität und eignen sich deshalb im Nachauflaufverfahren zur Sugar beets or potatoes. Some of the compounds according to the invention show a high selectivity and are therefore suitable for the postemergence process
Bekämpfung von unerwünschtem Pflanzenwuchs in landwirtschaftlichen Kulturen. Control of undesirable plant growth in agricultural crops.

Claims

Patentansprüche claims
1 . Azin-2-on-3-carboxamide der Formel (I) oder deren Salze 1 . Azin-2-one-3-carboxamides of the formula (I) or salts thereof
Figure imgf000038_0001
worin die Substituenten folgende Bedeutungen haben
Figure imgf000038_0001
wherein the substituents have the following meanings
R1 bedeutet (Ci-Cio)-Alkyl, (C2-Cio)-Alkenyl, (C2-Cio)-Alkinyl, Halogen-(Ci-Cio)- alkyl, Halogen-(C2-Cio)-alkenyl, Halogen-(C2-Cio)-alkinyl, (C3-Cio)-Cycloalkyl, Halogen- (C3-Cio)-cycloal kyl , (Ci -C )-Al kyl-(C3-C7)-cycloal kyl , (C3-C7)-Cycloal kyl-(Ci -C6)-al kyl , (C3-C7)-Cycloalkyl-(C3-C7)-cycloalkyl, Halogen-(C3-C7)-cycloalkyl-(Ci-C6)-alkyl, (Ci-C6)- Alkyl-(C3-C7)-cycloalkyl-(Ci-C6)-alkyl, (C3-Ci2)-Cycloalkenyl, Halogen-(C3-Ci2)- cycloalkenyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(C2-C6)-alkenyl, (Ci-C6)- Alkyl-(C3-C7)-cycloalkyl, (Ci-C6)-Alkoxy-(C3-C7)-cycloalkyl, (C3-C7)-Cycloalkoxy-(Ci- C6)-al kyl , (C3-C7)-Cycloal koxy-(Ci -C6)-al koxy-(Ci -C6)-al kyl , (Ci -C6)-Al koxy-(Ci -C6)- alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkylthio-(Ci-C6)-alkyl, (Ci-C6)-Alkylsulfinyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylsulfonyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylamino-(Ci-C6)-alkyl, Di-(Ci-Ce)- alkylamino-(Ci-C6)-alkyl, Halogen-(Ci-C6)-alkylamino-(Ci-C6)-alkyl, (C3-C7)- Cycloalkylamino-(Ci-C6)-alkyl, (Ci-C6)-Alkyl-carbonyl, Halogen-(Ci-C6)-alkyl-carbonyl, (C3-C7)-Cycloal kyl-carbonyl , (Ci-ΟΘ)-ΑΙ koxy-carbonyl , (C3-C7)-Cycloal koxy-carbonyl , (C3-C7)-Cycloalkyl-(Ci-C6)-alkoxy-carbonyl, (Ci-C6)-Alkylamino-carbonyl, Di-(Ci-Ce)- alkylamino-carbonyl, (C3-C7)-Cycloalkylamino-carbonyl, Cyano-(Ci-C6)-alkyl, Hydroxy- (Ci-C6)-alkyl, (C3-C7)-Cycloalkenyl-(Ci-C6)-alkyl, Halogen-(Ci-C6)-alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-halogen-(Ci-C6)-alkyl, Halogen-(Ci-C6)-alkoxy-halogen-(Ci-C6)-alkyl, Halogen-(C3-C7)-cycloalkoxy-(Ci-C6)-alkyl, (C3-C7)-Cycloalkenyloxy-(Ci-C6)-alkyl, Halogen-(C3-C7)-cycloalkenyloxy-(Ci-C6)-alkyl, Di-(Ci-C6)-alkoxy-(Ci-C6)-alkyl, (Ci-C6)- Alkoxy-(Ci-C6)-al kyl-carbonyl, (Ci-C6)-Alkoxy-carbonyl-(Ci-C6)-alkyl, Halogen-(Ci-C6)- al koxy-carbonyl, (Ci-Cio)-Alkoxy, Halogen-(Ci-Cio)-alkoxy, (C3-Ci2)-Cycloalkoxy, Halogen-(C3-C7)-cycloalkoxy, (C3-C7)-Cycloalkyl-(Ci-C6)-alkoxy, (C2-Ci2)-Alkenyloxy, Halogen-(C2-Cio)-alkenyloxy, (C2-Cio)-Alkinyloxy, Halogen-(C3-Cio)-alkinyloxy, (C1-C6)- alkoxy-(Ci-C6)-alkoxy, (Ci-C6)-Alkyl-carbonyloxy, Halogen-(C2-Ci2)-alkyl-carbonyloxy, (C3-C7)-Cycloal kyl-carbonyloxy, (Ci -ΟΘ)-ΑΙ kyl-carbonyl-(Ci -C6)-al koxy, (Ci -C10)- Alkylthio, Halogen-(Ci-Cio)-alkylthio, (C3-Ci2)-Cycloalkylthio, (Ci -Ci o)-AI kylsulfinyl , Halogen-(Ci-Cio)-alkylsulfinyl, (Ci-Cio)-alkylsulfonyl, Halogen-(Ci-Cio)-alkylsulfonyl, (C3-Ci2)-Cycloalkylsulfonyl, (Ci-C6)-Alkyl-carbonylthio, (Ci-C6)-Alkyl(thiocarbonyl)thio, (C3-Ci2)-Cycloalkylsulfinyl, (Ci-C6)-Alkylaminosulfonyl, Di-(Ci-C6)-alkylamino-sulfonyl, (Ci-C6)-Alkylamino, Di-(Ci-C6)-alkylamino, Halogen-(Ci-C6)-alkylamino, Halogen-di- (Ci-C6)-alkylamino, (C3-Ci2)-Cycloalkylamino, (Ci-C6)-Alkyl-carbonylamino, Halogen- (Ci-C6)-alkyl-carbonylamino, (Ci-Cio)-Alkylsulfonylamino, Halogen-(Ci-Cio)- alkylsulfonylamino, (C3-C7)-Cycloalkyl-(Ci-C6)-alkyl-amino, Cyano, Hydroxy, Amino, C(=O)OH, C(=O)NHOH, SO2NH2, SO2NHCN, SO2NHOH, NHCHO, G, W2G, W2OG, oder R 1 represents (C 1 -C 10) -alkyl, (C 2 -C 10) -alkenyl, (C 2 -C 10) -alkynyl, halogeno (C 1 -C 10) -alkyl, halogeno (C 2 -C 10) -alkenyl, halogen (C 2 -C 10) -alkynyl, (C 3 -C 10) -cycloalkyl, halogeno (C 3 -C 10) -cycloalkyl, (C 1 -C 6 ) -alkyl (C 3 -C 7 ) -cycloalkyl, ( C 3 -C 7 ) -cycloalkyl (C 1 -C 6 ) -alkyl, (C 3 -C 7 ) -cycloalkyl- (C 3 -C 7 ) -cycloalkyl, halogeno (C 3 -C 7 ) - cycloalkyl- (Ci-C 6) alkyl, (Ci-C 6) - alkyl (C 3 -C 7) cycloalkyl- (Ci-C 6) alkyl, (C3-Ci2) cycloalkenyl, halogen - (C 3 -C 2) - cycloalkenyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, (Ci-C6) alkoxy (C2-C6) alkenyl, (Ci-C 6 ) Alkyl (C 3 -C 7 ) cycloalkyl, (C 1 -C 6 ) alkoxy (C 3 -C 7 ) cycloalkyl, (C 3 -C 7 ) cycloalkoxy (C 1 -C 6 ) - al kyl, (C 3 -C 7 ) -cycloalkoxy (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy (C 1 -C 6 ) - alkoxy- (Ci-C 6 ) -alkyl, (Ci-C6) -alkylthio (Ci-C 6 ) -alkyl, (Ci-C6) -alkylsulfinyl- (Ci-C 6 ) -alkyl, (Ci-C6 ) -Alkylsulfonyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylamino- (C 1 -C 6 ) -alkyl, di- (C 1 -C 6 ) -alkylamino- (C 1 -C 6 ) -alkyl, Halogeno (C 1 -C 6 ) -alkylamino (C 1 -C 6 ) -alkyl, (C 3 -C 7 ) -cycloalkylamino (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylcarbonyl, halogeno (Ci -C6) -alkyl-carbonyl, (C 3 -C 7 ) -cycloalkyl-carbonyl, (Ci-ΟΘ) -ΑΙ-carboxy-carbonyl, (C 3 -C 7 ) -cycloalkoxy-carbonyl, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 6 ) -alkoxycarbonyl, (C 1 -C 6 ) -alkylamino-carbonyl, di- (C 1 -C 6 ) -alkylaminocarbonyl, (C 3 -C 7 ) -cycloalkylaminocarbonyl, cyano - (Ci-C6) alkyl, hydroxy (Ci-C 6) alkyl, (C 3 -C 7) cycloalkenyl (Ci-C 6) alkyl, halo (Ci-C6) alkoxy ( C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy-halogeno (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkoxy-halogeno (C 1 -C 6 ) -alkyl, halogeno (C 3 -C 7 ) -cycloalkoxy- (C 1 -C 6 ) -alkyl, (C 3 -C 7 ) -cycloalkenyloxy- (C 1 -C 6 ) -alkyl, halogeno (C 3 -C 7 ) -cycloalkenyloxy- (C 1 -C 7 ) -cycloalkoxy- (C 1 -C 6 ) -alkyl 6 ) -alkyl, di- (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl-carbonyl, (C 1 -C 6 ) - Alkoxycarbonyl- (C 1 -C 6) -alkyl, halogen- (C 1 -C 6) -alkoxy-carbonyl, (C 1 -C 10) -alkoxy, halogeno (C 1 -C 10) -alkoxy, (C 3 -C 12) - Cycloalkoxy, halo (C 3 -C 7 ) -cycloalkoxy, ( C 3 -C 7 ) -cycloalkyl- (C 1 -C 6 ) -alkoxy, (C 2 -C 12) -alkenyloxy, halo (C 2 -C 10) -alkenyloxy, (C 2 -C 10) -alkynyloxy, halogeno (C 3 -Cio) -alkynyloxy, (C1-C6) - alkoxy- (C 1 -C 6) -alkoxy, (C 1 -C 6) -alkyl-carbonyloxy, halogeno (C 2 -C 12) -alkyl-carbonyloxy, (C 3 -C 7) -cycloalkyl-carbonyloxy, (C 1 -C 4) -ΑΙ kyl-carbonyl- (C 1 -C 6) -alkoxy, (C 1 -C 10) -alkylthio, halogeno (C 1 -C 10) -alkylthio, (C 3 -C 12) -cycloalkylthio, (C 1 -C 10) -alkylsulfinyl, Halogeno- (C 1 -C 10) -alkylsulfinyl, (C 1 -C 10) -alkylsulfonyl, halogeno (C 1 -C 10) -alkylsulfonyl, (C 3 -C 12) -cycloalkylsulfonyl, (C 1 -C 6 ) -alkylcarbonylthio, (Ci -C 6 ) -alkyl (thiocarbonyl) thio, (C 3 -C 12) -cycloalkylsulfinyl, (C 1 -C 6 ) -alkylaminosulfonyl, di- (C 1 -C 6 ) -alkylaminosulfonyl, (C 1 -C 6 ) -alkylamino, di- ( C 1 -C 6) -alkylamino, halogeno (C 1 -C 6) -alkylamino, halo-di- (C 1 -C 6) -alkylamino, (C 3 -C 12) -cycloalkylamino, (C 1 -C 6) -alkylcarbonylamino, halogeno ( C 1 -C 6) -alkyl-carbonylamino, (C 1 -C 10) -alkylsulfonylamino, halogeno (C 1 -C 10) -alkylsulfonylamino, (C 3 -C 7) -cycloalkyl- (C 1 -C 6) -alkyl-amino, cyano, hydroxy, amino , C (= O) OH, C (= O) NHOH, SO 2 NH 2, SO 2 NHCN, SO2NHOH, NHCHO, G, W 2 G, W 2 OG, or
R1 bedeutet Phenyl, Phenylsulfonyl, W1-(Phenyl), W1-(O-Phenyl), W1-(S-Phenyl), W1-(SO2-Phenyl), W2-(SO2CH2-Phenyl) oder W2-(SCH2-Phenyl), wobei die Phenylringe der acht vorstehend genannten Reste jeweils s Substituenten R6 tragen, R 1 is phenyl, phenylsulfonyl, W 1 - (phenyl), W 1 - (O-phenyl), W 1 - (S-phenyl), W 1 - (SO 2 -phenyl), W 2 - (SO 2 CH 2 Phenyl) or W 2 - (SCH 2 -phenyl), where the phenyl rings of the eight abovementioned radicals each carry s substituents R 6 ,
X1 bedeutet N oder CR2a, X 1 is N or CR 2a ,
X2 bedeutet N oder CR2b, X 2 is N or CR 2b ,
R2a bedeutet Phenyl oder W3-(Phenyl), wobei die Phenylringe der zwei vorstehend genannten Reste jeweils s Substituenten R6 tragen, oder R 2a is phenyl or W 3 - (phenyl), wherein the phenyl rings of the two radicals mentioned above each carry s substituents R 6 , or
R2a bedeutet G, W4G, Wasserstoff, Cyano, Amino, Nitro, CHO, C(=O)OH, R 2a represents G, W 4 G, is hydrogen, cyano, amino, nitro, CHO, C (= O) OH,
C(=O)NH2, C(=S)NH2, C(=O)NHCN, C(=O)NHOH, SH, SO2NH2, SO2NHCN, C (= O) NH 2 , C (= S) NH 2 , C (= O) NHCN, C (= O) NHOH, SH, SO 2 NH 2 , SO 2 NHCN,
SO2NHOH, SF5, NHCHO, NHNH2, NHOH, NHCN, NHC(O)NH2, (Ci-C10)-Alkyl, (C2- Cio)-Alkenyl, (C2-Cio)-Alkinyl, Halogen-(Ci-Cio)-alkyl, Halogen-(C2-Cio)-alkenyl, Halogen-(C2-Cio)-alkinyl, (C3-C8)-Cycloalkyl, Halogen-(C3-C8)-cycloalkyl, (Ci-Ce)-Alkyl- (C3-C7)-cycloal kyl , (C3-C7)-Cycloal kyl-(Ci -C6)-al kyl , (Ci -C6)-Cycloal kyl-(Ci -C6)- cycloalkyl, Halogen-(Ci-C6)-Cycloalkyl-(Ci-C6)-alkyl, (Ci-C6)-Alkyl-(C3-C7)-cycloalkyl- (Ci-C6)-alkyl, (C3-C8)-Cycloalkenyl, Halogen-(C3-C8)-Cycloalkenyl, (Ci-Ce)-Alkoxy (C1- C6)-alkyl, (C1 -C6)-Alkoxy (Ci-C6)-alkenyl, (Ci-C6)-Alkyl-(C3-C7)-cycloalkyl, (Ci-C6)- Al koxy-(C3-C7)-cycloal kyl , (Ci -C6)-Cycloal koxy-(Ci -C6)-al kyl , (C3-C7)-Cycloal koxy-(Ci - C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxy-(Ci-C6)-alkyl, (C2-C8)-Al ky Ith ioal ky I , (Ci-C6)- Alkylsulfinyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylsulfonyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylamino-(Ci- C6)-alkyl, Di-(Ci-C6)-alkylamino-(Ci-C6)-alkyl, Halogen-(Ci-C6)-alkylamino-(Ci-C6)- alkyl, (C3-C7)-Cycloalkylamino-(Ci-C6)-alkyl, (Ci-C6)-Alkyl-carbonyl, Halogen-(Ci-C6)- alkyl-carbonyl, (C3-C7)-Cycloalkyl-carbonyl, (Ci-C6)-Alkoxy-carbonyl, (C3-C7)- Cycloalkoxy-carbonyl, (C3-C7)-Cycloalkyl-(Ci-C6)-alkoxy-carbonyl, (Ci-C6)-Alkylamino- carbonyl, Di-(Ci-C6)-alkyl-amino-carbonyl, (C3-C7)-Cycloalkyl-amino-carbonyl, Cyano- (Ci-C6)-alkyl, Hydroxy-(Ci-C6)-alkyl, (C3-C7)-Cycloalkenyl-(Ci-C6)-alkyl, Halogen-(Ci- C6)-alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-halogen-alkyl, Halogen-(Ci-Ce)- alkoxy-(Ci-C6)-halogen-alkyl, Halogen-(C3-C7)-cycloalkoxy-(Ci-C6)-alkyl, (C3-C7)- Cycloalkenyloxy-(Ci-C6)-alkyl, Halogen-(C3-C7)-cycloalkenyloxy-(Ci-C6)-alkyl, Di-(Ci- C6)-alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl-carbonyl, (Ci-C6)-Alkoxy- carbonyl-(Ci-C6)-alkyl, Halogen-(Ci-C6)-alkoxy-carbonyl, (Ci-C6)-Alkoxy, Halogen-(Ci- C6)-alkoxy, (C3-C8)-Cycloalkoxy, Halogen-(C3-C8)-cycloalkoxy, (C3-C7)-Cycloalkyl-(Ci- C6)-alkoxy, (C2-C6)-Alkenyloxy, Halogen-(C2-C6)-alkenyloxy, (C2-C6)-Alkinyloxy, Halogen-(C3-C6)-alkinyloxy, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxy, (Ci-C8)-Alkyl-carbonyloxy, Halogen-(Ci-C8)-alkylcarbonyloxy, (C3-C7)-Cycloalkyl-carbonyloxy, (Ci-Ce)-Alky- carbonyl-(Ci-C6)-alkoxy, (Ci-C6)-Alkylthio, Halogen-(Ci-C6)-alkylthio, (C3-C8)- Cycloalkylthio, (Ci-C6)-Alkylsulfinyl, Halogen-(Ci-C6)-alkylsulfinyl, (Ci-C6)-Alkylsulfonyl, Halogen-(Ci-C6)-alkylsulfonyl, (C3-Cio)-Cycloalkylsulfonyl, (Ci-C6)-Alkylcarbonylthio, (Ci-C6)-Alkyl(thiocarbonyl)thio, (C3-C8)-Cycloalkylsulfinyl, (Ci-C6)-Alkylaminosulfonyl, Di-(Ci-C6)-alkylaminosulfonyl, (Ci-C6)-Alkylamino, Di-(Ci-C6)-alkylamino, Halogen-(Ci- C6)-alkylamino, Halogen-di-(Ci-C6)-alkylamino, (C3-C8)-Cycloalkylamino, (C2-C8)- Alkylcarbonylamino, Halogen-(C2-C8)-alkylcarbonylamino, (Ci-Cio)-Alkylsulfonylamino, Halogen-(Ci-Cio)-alkylsulfonylamino, (C3-C7)-Cycloalkyl-(Ci-C6)-alkyl-amino oder Halogen-tri-(Ci-C4)-alkylsilyl, SO2NHOH, SF 5, NHCHO, NHNH 2, NHOH, NHCN, NHC (O) NH2, (Ci-C10) alkyl, (C 2 - Cio) alkenyl, (C2 -Cio) alkynyl, halo ( C 1 -C 10) -alkyl, halogeno (C 2 -C 10) -alkenyl, halogeno (C 2 -C 10) -alkynyl, (C 3 -C 8 ) -cycloalkyl, halogeno (C 3 -C 8 ) -cycloalkyl , (C 1 -C 6 ) -alkyl (C 3 -C 7 ) -cycloalkyl, (C 3 -C 7 ) -cycloalkyl (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -cycloalkyl - (Ci-C6) - cycloalkyl, halo (Ci-C6) -cycloalkyl- (Ci-C 6) alkyl, (Ci-C 6) -alkyl- (C 3 -C 7) cycloalkyl- (C -C 6 ) -alkyl, (C 3 -C 8 ) -cycloalkenyl, halo (C 3 -C 8 ) -cycloalkenyl, (Ci-Ce) -alkoxy (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) alkoxy (Ci-C 6) alkenyl, (Ci-C 6) -alkyl- (C 3 -C 7) cycloalkyl, (Ci-C 6) - Al alkoxy- (C 3 -C 7) -cycloal kyl, (C 1 -C 6 ) -cycloalkoxy (C 1 -C 6 ) -alkyl, (C 3 -C 7 ) -cycloalkoxy (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy (Ci-C6) alkoxy (Ci-C 6) alkyl, (C 2 -C 8) -alkyl ky Ith ioal ky I, (Ci-C 6) - alkylsulfinyl (Ci-C6) alkyl, ( C 1 -C 6 ) -alkylsulfonyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylamino- (C 1 -C 4 ) -alkyl C 6) alkyl, di (Ci-C6) alkylamino (Ci-C6) alkyl, halo (Ci-C6) alkylamino (Ci-C 6) - alkyl, (C3-C7) - Cycloalkylamino- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylcarbonyl, halogeno (C 1 -C 6 ) -alkylcarbonyl, (C 3 -C 7) -cycloalkylcarbonyl, (C 1 -C 6 ) - Alkoxycarbonyl, (C 3 -C 7) -cycloalkoxycarbonyl, (C 3 -C 7) -cycloalkyl- (C 1 -C 6) -alkoxycarbonyl, (C 1 -C 6) -alkylaminocarbonyl, di- (C 1 -C 6) alkylamino-carbonyl, (C 3 -C 7 ) -cycloalkylamino-carbonyl, cyano- (C 1 -C 6 ) -alkyl, hydroxy- (C 1 -C 6 ) -alkyl, (C 3 -C 7 ) -cycloalkenyl- (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -haloalkyl, halogeno (Ci -Ce) - alkoxy- (C 1 -C 6) -haloalkyl, halogeno (C 3 -C 7) -cycloalkoxy- (C 1 -C 6) -alkyl, (C 3 -C 7) -cycloalkenyloxy- (C 1 -C 6) -alkyl, halo (C3 C7) -cycloalkenyloxy- (Ci-C6) alkyl, di (Ci- C6) alkoxy (Ci-C 6) alkyl, (Ci-C6) alkoxy (Ci-C 6 ) -alkyl-carbonyl, (C 1 -C 6) -alkoxycarbonyl- (C 1 -C 6) -alkyl, halogeno (C 1 -C 6) -alkoxycarbonyl, (C 1 -C 6) -alkoxy, halogeno-C 1 -C 6 ) -alkoxy, (C3-C8) -cycloalkoxy, halo (C3-C8) -c ycloalkoxy, (C 3 -C 7) -cycloalkyl- (C 1 -C 6) -alkoxy, (C 2 -C 6) -alkenyloxy, halo (C 2 -C 6) -alkenyloxy, (C 2 -C 6) -alkynyloxy, halogeno-C 3 -C 6 ) -alkynyloxy, (C 1 -C 6) -alkoxy- (C 1 -C 6) -alkoxy, (C 1 -C 8) -alkyl-carbonyloxy, halogeno (C 1 -C 8) -alkylcarbonyloxy, (C 3 -C 7) -cycloalkyl-carbonyloxy, (Ci-Ce) -Alky- carbonyl- (Ci-C 6) alkoxy, (Ci-C 6) alkylthio, halo (Ci-C 6) -alkylthio, (C 3 -C 8) - cycloalkylthio, ( C 1 -C 6 ) -alkylsulfinyl, halogeno (C 1 -C 6 ) -alkylsulfinyl, (C 1 -C 6 ) -alkylsulfonyl, halogeno (C 1 -C 6 ) -alkylsulfonyl, (C 3 -C 10) -cycloalkylsulfonyl, (C 1 -C 6 ) ) -Alkylcarbonylthio, (C 1 -C 6) -alkyl (thiocarbonyl) thio, (C 3 -C 8) -cycloalkylsulfinyl, (C 1 -C 6) -alkylaminosulfonyl, di- (C 1 -C 6) -alkylaminosulfonyl, (C 1 -C 6) -alkylamino, Di- (C 1 -C 6) -alkylamino, halogeno (C 1 -C 6) -alkylamino, halo-di- (C 1 -C 6) -alkylamino, (C 3 -C 8) -cycloalkylamino, (C 2 -C 8) -alkylcarbonylamino, halogeno (C 2 -C 8) -alkylcarbonylamino, (C 1 -C 10) -alkylsulfonylamino, halogeno (C 1 -C 10) -alkylsulfonylamino, (C 3 -C 7) -cycloalkyl- (C 1 -C 6) -alkylamino or halo-tri- (C 1 -C 4) -alkylcarbonylamino, (C 1 -C 10) -alkylsulfonylamino -C 4 ) Alkylsilyl,
R2b bedeutet Wasserstoff, Halogen, Cyano, Nitro, (Ci-C )-Alkyl, (Ci-C )-Haloalkyl, (C2-C6)-Alkenyl, (C2-C6)-Halogenalkenyl, (C2-C6)-Alkinyl, (C2-C6)-Halogenalkinyl, (C3- C6)-Cycloalkyl, (C3-C6)-Halogencycloalkyl, (Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, (C3-C6)- Cycloalkyl-(Ci-C6)-alkyl, (Ci-C )-Alkoxy oder (Ci-C )-Haloalkoxy, R 2b is hydrogen, halogen, cyano, nitro, (Ci-C) alkyl, (Ci-C) -haloalkyl, (C2-C6) alkenyl, (C2-C6) haloalkenyl, (C2-C6 ) alkynyl, (C2-C6) -haloalkynyl, (C 3 - C 6) cycloalkyl, (C3-C 6) halocycloalkyl, (Ci-C6) alkyl-O- (Ci-C 6) alkyl , (C 3 -C 6) - cycloalkyl, (Ci-C 6) alkyl, (Ci-C) alkoxy or (Ci-C) haloalkoxy,
Q bedeutet einen Rest Q1 , Q2, Q3 oder Q4,
Figure imgf000041_0001
Q is a radical Q 1 , Q 2 , Q 3 or Q 4 ,
Figure imgf000041_0001
R3 bedeutet (Ci-C8)-Alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, wobei diese Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Cyano, Hydroxy, Nitro, SiR10 3, PO(OR10)2, S(O)n-(Ci-C6)-Alkyl, (Ci-C6)-Alkoxy, Halogen-(Ci-C6)-alkoxy, COR3a, COOR3a, OCOR3a, NR3aCOR3a, NR3aSO2R3b, (C3-C6)-Cycloalkyl, Heteroaryl, Heterocyclyl oder Phenyl substituiert sind, wobei die 4 letztgenannten Reste jeweils durch p Reste aus der Gruppe bestehend aus Methyl, Ethyl, Methoxy, Trifluornnethyl, Cyano und Halogen substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, oder R 3 is (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, where these radicals are each represented by s radicals from the group consisting of halogen, cyano, hydroxyl, nitro, SiR 10 3, PO (OR 10) 2, S (O) n - (Ci-C 6) -alkyl, (Ci-C 6) alkoxy, halo (Ci-C 6) alkoxy, COR 3a , COOR 3a , OCOR 3a , NR 3a COR 3a , NR 3a SO 2 R 3b , (C 3 -C 6 ) cycloalkyl, heteroaryl, heterocyclyl or phenyl are substituted, wherein the 4 latter radicals each by p radicals from the group from methyl, ethyl, methoxy, trifluoromethyl, cyano and halogen, and wherein heterocyclyl n carries oxo groups, or
R3 bedeutet Phenyl, das durch p Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, S(O)n-(Ci-C6)- Alkyl, (Ci-Ce)-Alkoxy, Halogen-(Ci-C6)-alkoxy und (Ci-C6)-Alkoxy-(Ci-C )-alkyl substituiert ist, R 3 is phenyl which is represented by p radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy and (C 1 -C 6 ) -alkoxy- (C 1 -C 4) -alkyl is
R3a bedeutet Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (C3-C6)- Cycloalkyl oder (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl oder Phenyl, R 3a is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl or (C 3 -C 6 ) - Cycloalkyl- (C 1 -C 6) -alkyl or phenyl,
R3b bedeutet (Ci-C6)-Alkyl, (C2-C6)-Alkenyl oder (C2-C6)-Alkinyl, (C3-C6)-Cycloalkyl oder (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl oder Phenyl, R 3b represents (Ci-C 6) -alkyl, (C 2 -C 6) -alkenyl or (C 2 -C 6) -alkynyl, (C3-C6) -cycloalkyl or (C3-C6) -cycloalkyl- ( C 1 -C 6 ) -alkyl or phenyl,
R4 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (C3-C7)-cyclo-Alkyl, Halogen-(Ci-C6)-alkyl, (Ci-Ce)-Alkoxy, Halogen-(Ci-C6)-alkoxy, (C2-C6)-Alkenyl, (C2-C6)-Alkenyloxy, (C2-C6)- Halogenalkenyl, (C2-C6)-Alkinyl, (C2-C6)-Alkinyloxy, (C2-C6)-Halogenalkinyl, (Ci-C6)- Alkoxy-(Ci-C6)-Alkyl, Cyano, Nitro, Methylsulfenyl, Methylsulfinyl, Methylsulfonyl, Acetylamino, Benzoylamino, Methoxycarbonyl, Ethoxycarbonyl, R 4 represents hydrogen, (Ci-C 6) -alkyl, (C 3 -C 7) -cycloalkyl, halo (Ci-C 6) alkyl, (Ci-Ce) alkoxy, halo (Ci- C 6) alkoxy, (C 2 -C 6) alkenyl, (C 2 -C 6) alkenyloxy, (C 2 -C 6) - haloalkenyl, (C 2 -C 6) -alkynyl, (C 2 - C 6) -alkynyloxy, (C 2 -C 6) haloalkynyl, (Ci-C6) - alkoxy- (Ci-C6) alkyl, cyano, nitro, methylsulphenyl, methylsulphinyl, methylsulphonyl, acetylamino, benzoylamino, methoxycarbonyl, ethoxycarbonyl .
Methoxycarbonylmethyl, Ethoxycarbonylmethyl, Benzoyl, Methylcarbonyl, Methoxycarbonylmethyl, ethoxycarbonylmethyl, benzoyl, methylcarbonyl,
Piperidinylcarbonyl, Trifluormethylcarbonyl, Halogen, Amino, Aminocarbonyl, Piperidinylcarbonyl, trifluoromethylcarbonyl, halogen, amino, aminocarbonyl,
Methylaminocarbonyl, Dimethylaminocarbonyl, Methoxymethyl, oder jeweils durch p Reste aus der Gruppe bestehend aus Methyl, Ethyl, Methoxy, Methylaminocarbonyl, dimethylaminocarbonyl, methoxymethyl, or in each case by p radicals from the group consisting of methyl, ethyl, methoxy,
Trifluormethyl und Halogen substituiertes Heteroaryl, Heterocyclyl oder Phenyl, Trifluoromethyl and halogen substituted heteroaryl, heterocyclyl or phenyl,
R5 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-Alkyl, CH2R5a, (C3- C7)-Cycloalkyl, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-alkenyl, (C2- CeJ-Alkinyl, Halogen-(C2-C6)-alkinyl, OR6, NHR6, Methoxycarbonyl, Ethoxycarbonyl, Methoxycarbonylmethyl, Ethoxycarbonylmethyl, Methylcarbonyl, R 5 represents hydrogen, (Ci-C 6) -alkyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, CH 2 R 5a, (C 3 - C 7) cycloalkyl, halo ( Ci-C 6) alkyl, (C2-C6) alkenyl, halo (C2-C6) alkenyl, (C 2 - CeJ-alkynyl, halo (C2-C6) alkynyl, OR 6, NHR 6 , methoxycarbonyl, ethoxycarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, methylcarbonyl,
Trifluormethylcarbonyl, Dimethylamino, Acetylamino, Methylsulfenyl, Methylsulfinyl, Methylsulfonyl oder jeweils durch p Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (Cs-CeJ-Cycloalkyl, S(O)n-(Ci-C6)- Alkyl, (Ci-C6)-Alkoxy, Halogen-(Ci-C6)-alkoxy, (Ci-C6)-Alkoxy-(Ci-C )-alkyl Trifluoromethylcarbonyl, dimethylamino, acetylamino, methylsulfenyl, methylsulfinyl, methylsulfonyl or in each case by p radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, CeJ-cycloalkyl, S (O) n - (Ci-C 6) - alkyl, (Ci-C 6) alkoxy, halo (Ci-C 6) alkoxy, (Ci-C6) alkoxy (Ci- C) -alkyl
substituiertes Heteroaryl, Heterocyclyl, Benzyl oder Phenyl, substituted heteroaryl, heterocyclyl, benzyl or phenyl,
R5a bedeutet Acetoxy, Acetamido, N-Methylacetamido, Benzoyloxy, Benzamido, N- Methylbenzamido, Methoxycarbonyl, Ethoxycarbonyl, Benzoyl, Methylcarbonyl, Piperidinylcarbonyl, Morpholinylcarbonyl, Trifluormethylcarbonyl, Aminocarbonyl, Methylaminocarbonyl, Dimethylaminocarbonyl, (Ci-C6)-Alkoxy, (C3-C6)-Cycloalkyl oder jeweils durch p Reste aus der Gruppe bestehend aus Methyl, Ethyl, Methoxy, R 5a represents acetoxy, acetamido, N-methylacetamido, benzoyloxy, benzamido, N-methylbenzamido, methoxycarbonyl, ethoxycarbonyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, morpholinylcarbonyl, trifluoromethylcarbonyl, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, (Ci-C6) -alkoxy, (C3-) C 6) -cycloalkyl or in each case by p radicals from the group consisting of methyl, ethyl, methoxy,
Trifluormethyl und Halogen substituiertes Heteroaryl oder Heterocyclyl, Trifluoromethyl and halogen substituted heteroaryl or heterocyclyl,
Y bedeutet O oder S, Y is O or S,
W1 bedeutet (Ci-Cio)-Alkylen, (C2-C6)-Alkenylen oder (C2-C6)-Alkinylen, W2, W3 und W4 bedeuten jeweils (Ci-Cio)-Alkylen, W 1 represents (Ci-Cio) alkylene, (C 2 -C 6) -alkenylene or (C2-C6) alkynylene, W 2, W 3 and W 4 each represents (Ci-Cio) alkylene,
G bedeutet jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-C6)-Alkoxy, Halogen-(Ci-C6)-alkoxy und (Ci-C6)-Alkoxy-(Ci-C4)-alkyl substituiertes Heteroaryl oder Heterocyclyl, wobei Heterocyclyl n Oxogruppen trägt, G means each consisting of halogen, nitro, cyano substituted by s radicals selected from the group (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C3-C6) -cycloalkyl, S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy and (C 1 -C 6 ) -alkoxy- (C 1 -C 4 ) -alkyl-substituted heteroaryl or heterocyclyl, where heterocyclyl carries n oxo groups,
R6 bedeutet Halogen, Cyano, Hydroxy, Amino, Nitro, -CHO, -C(=O)OH, R 6 is halogen, cyano, hydroxy, amino, nitro, -CHO, -C (= O) OH,
-C(=O)NH2, -C(=S)NH2, -C(=O)NHCN, -C(=O)NHOH, -SH, -SO2NH2, -SO2NHCN, -SO2NHOH, -OCN, -SCN, -SF5, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, Halogen-(Ci-C6)-alkyl, Halogen-(C2-C6)-alkenyl, Halogen-(C2-C6)-alkinyl, (C3-C8)- Cycloalkyl, Halogen-(C3-C8)-cycloalkyl, (Ci-C6)-Alkyl-(C3-C7)-cycloalkyl, (C3-C7)- Cycloalkyl-(Ci-C6)-alkyl, (C3-C8)-Cycloalkenyl, Halogen-(C3-C8)-cycloalkenyl, (C1-C-6)- Al koxy-(Ci -C6)-al kyl , (C3-C7)-Cycloal koxy-(Ci -C6)-al kyl , (C1 -C6)-Al koxy-(Ci -C6)-al koxy- (Ci-C6)-alkyl, (C1 -C6)-Al kylth io-(Ci -C6)-al kyl , (Ci-C8)-Alkylsulfinyl-(Ci-C6)-alkyl, (Ci-C8)- Alkoxy-halogen-(Ci-C6)-alkyl, Cyano-(Ci-C6)-alkyl, Hydroxy-(Ci-C6)-alkyl, (Ci-C6)- Alkoxy, Halogen-(Ci-C6)-alkoxy, (C3-C8)-Cycloalkoxy, Halogen-(C3-C8)-cycloalkoxy, (C3-C8)-Cycloalkyl-(Ci-C6)-alkoxy, (C2-C6)-Alkenyloxy, Halogen-(C2-C6)-alkenyloxy, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxy, (C2-C6)-Alkylcarbonyloxy, (Ci-C6)-Alkylthio, Halogen- (Ci-Ce)-al kylth io, (C3-C8)-Cycloal kylth io, (Ci-C6)-Alkylsulfinyl, Halogen-(Ci-Ce)- alkylsulfinyl, (Ci-C6)-Alkylsulfonyl, Halogen-(Ci-C6)-alkylsulfonyl, (C3-C8)- Cycloalkylsulfonyl, (Ci-C6)-Alkylamino, Di-(Ci-C6)-alkylamino, Halogen-(Ci-C6)- alkylamino, Halogen-di-(Ci-C8)-alkylamino oder (C3-C8)-Cycloalkylamino, oder zwei vicinale Reste R6 bilden eine (C3-C6)-Alkylengruppe, in der p Kohlenstoffatonne durch Sauerstoff, Schwefel oder Stickstoff ersetzt sind, und in der ein Kohlenstoffatom t Oxogruppen trägt, n bedeutet 0, 1 oder 2, p bedeutet 0, 1 , 2 oder 3, s bedeutet 0, 1 , 2, 3, 4 oder 5, t bedeutet 0 oder 1 . -C (= O) NH 2, -C (= S) NH 2, -C (= O) NHCN, -C (= O) NHOH, -SH, -SO2NH2, -SO2NHCN, -SO2NHOH, -OCN, - SCN, -SF 5, (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl, Halogeno (C 1 -C 6 ) -alkyl, halogeno (C 2 -C 6 ) -alkenyl, halogeno (C 2 -C 6 ) -alkynyl, (C 3 -C 8 ) -cycloalkyl, halogeno (C 3 -C 8 ) -cycloalkyl, (C 1 -C 6 ) -alkyl (C 3 -C 7 ) -cycloalkyl, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 3 -C 8) -cycloalkenyl, and halogen- (C 3 -C 8) -cycloalkyl- (C 1 -C 6 ) -alkyl cycloalkenyl, (C1-C-6) - Al alkoxy- (Ci-C6) -alkyl, (C 3 -C 7) -Cycloal alkoxy- (Ci-C6) -alkyl, (C1-C6) -Al koxy- (Ci -C 6 ) -alkoxy- (Ci-C 6 ) -alkyl, (C 1 -C 6 ) -Al kylth io- (Ci -C 6 ) -alcyl, (Ci-C 8 ) alkylsulfinyl (Ci-C 6) alkyl, (Ci-C8) - alkoxy-halo (Ci-C 6) alkyl, cyano (Ci-C 6) alkyl, hydroxy (Ci-C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy, (C 3 -C 8) -cycloalkoxy, halogeno (C 3 -C 8) -cycloalkoxy, (C 3 -C 8) -cycloalkyl- ( C 1 -C 6 ) -alkoxy, (C 2 -C 6 ) -alkenyloxy, halogeno (C 2 -C 6 ) -alkenyloxy, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkoxy, (C 2 -C 6 ) -alkylcarbonyloxy , (C 1 -C 6 ) -alkylthio, halogen- (C 1 -C 6 ) -alkylthio, (C 3 -C 8 ) -cycloalkylthio, (C 1 -C 6 ) -alkylsulfinyl, halogen- (C 1 -C 6 ) alkylsulfinyl, (C 1 -C 6 ) -alkylsulfonyl, halo (C 1 -C 6 ) -alkylsulfonyl, (C 3 -C 8 ) -cycloalkylsulfonyl, (C 1 -C 6 ) -alkylamino, di (C 1 -C 6 ) -alkylamino, halogeno (C 1 -C 6 ) -alkylamino, halo-di- (C 1 -C 8 ) -alkylamino or (C 3 -C8) -cycloalkylamino, or two vicinal radicals R 6 form a (C3-C6) -alkylene group in which p Kohlenstoffatonne replaced by oxygen, sulfur or nitrogen, and in which a carbon atom t carries oxo groups, n means 0, 1 or 2, p is 0, 1, 2 or 3, s is 0, 1, 2, 3, 4 or 5, t is 0 or 1.
2. Azin-2-on-3-carboxamide der Formel (I) oder deren Salze nach Anspruch 1 , worin 2. azin-2-one-3-carboxamides of the formula (I) or salts thereof according to claim 1, wherein
R1 bedeutet (Ci-Cio)-Alkyl, (C2-Cio)-Alkenyl, (C2-Cio)-Alkinyl, Halogen-(Ci-Cio)- alkyl, Halogen-(C2-Cio)-alkenyl, Halogen-(C2-Cio)-alkinyl, (C3-Cio)-Cycloalkyl, Halogen- (C3-Cio)-cycloal kyl , (C1 -C )-Al kyl-(C3-C7)-cycloal kyl , (C3-C7)-Cycloal kyl- (Ci-C6)-alkyl, (C3-C7)-Cycloalkyl-(C3-C7)-cycloalkyl, Halogen-(C3-C7)-cycloalkyl- (C1 -C6)-al kyl , (C1 -C6)-Al kyl-(C3-C7)-cycloal kyl-(Ci -C6)-al kyl , (C3-Ci2)-Cycloal kenyl , Halogen-(C3-Ci2)-cycloalkenyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(C2-C6)- alkenyl, (Ci-C6)-Alkyl-(C3-C7)-cycloalkyl, (Ci-C6)-Alkoxy-(C3-C7)-cycloalkyl, (C3-C7)- Cycloal koxy-(Ci -C6)-al kyl , (C3-C7)-Cycloal koxy-(Ci -C6)-al koxy-(Ci -C6)-al kyl , (Ci -C6)- Al koxy-(Ci -C6)-al koxy-(Ci -C6)-al kyl , (Ci -C6)-Al kylth io-(Ci -C6)-al kyl , (Ci -C6)- Alkylsulfinyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylsulfonyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylamino- (Ci-C6)-alkyl, Di-(Ci-C6)-alkylamino-(Ci-C6)-alkyl, Halogen-(Ci-C6)-alkylamino- (Ci-C6)-alkyl, (C3-C7)-Cycloalkylamino-(Ci-C6)-alkyl, (Ci-C6)-Alkyl-carbonyl, Halogen- (Ci -C6)-al kyl-carbonyl , (C3-C7)-Cycloal kyl-carbonyl , (Ci -ΟΘ)-ΑΙ koxy-carbonyl , R 1 represents (C 1 -C 10) -alkyl, (C 2 -C 10) -alkenyl, (C 2 -C 10) -alkynyl, halogeno (C 1 -C 10) -alkyl, halogeno (C 2 -C 10) -alkenyl, halogen - (C 2 -C 10) -alkynyl, (C 3 -C 10) -cycloalkyl, halogeno (C 3 -C 10) -cycloalkyl, (C 1 -C 6 ) -alkyl (C 3 -C 7 ) -cycloalkyl, ( C 3 -C 7 ) -cycloalkyl (C 1 -C 6 ) -alkyl, (C 3 -C 7 ) -cycloalkyl- (C 3 -C 7 ) -cycloalkyl, halogeno (C 3 -C 7 ) -cycloalkyl - (C 1 -C 6 ) -alcyl, (C 1 -C 6 ) -alkyl (C 3 -C 7 ) -cycloalkyl (C 1 -C 6 ) -alkyl, (C 3 -C 2 ) - Cycloalkenyl, Halogeno- (C 3 -C 12) -cycloalkenyl, (C 1 -C 6) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 2 -C 6 ) -alkenyl, (C 1 -C 6 ) alkyl- (C 3 -C 7) cycloalkyl, (Ci-C 6) alkoxy (C3-C7) cycloalkyl, (C 3 -C 7) - cycloalkylene alkoxy- (Ci-C6) -al kyl, (C 3 -C 7 ) -cycloalkoxy (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) - al koxy- (C 1 -C 6 ) -alkenyl, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylsulfinyl- (C 1 -C 6 ) - alkyl, (C 1 -C 6 ) -alkylsulfonyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylamino- (C 1 -C 6 ) -alkyl, di- (C 1 -C 6 ) -alkylamino- (C 1 -C 6 ) -alkyl ) -alkyl, halo (C 1 -C 6 ) -alkylamino (C 1 -C 6 ) -alkyl, (C 3 -C 7 ) -cycloalkylamino (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkyl) carbonyl, halogen- (C 1 -C 6 ) -alkenyl-carbonyl, (C 3 -C 7 ) -cycloalkyl-carbonyl, (C 1 -C 4 ) -alkoxy-carbonyl,
(C3-C7)-Cycloal koxy-carbonyl , (C3-C7)-Cycloal kyl-(Ci -C6)-al koxy-carbonyl , (Ci -Ce)- Alkylamino-carbonyl, Di-(Ci-C6)-alkylamino-carbonyl, (C3-C7)-Cycloalkylamino- carbonyl, Cyano-(Ci-C6)-alkyl, Hydroxy-(Ci-C6)-alkyl, (C3-C7)-Cycloalkenyl-(Ci-C6)- alkyl, Halogen-(Ci-C6)-alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-halogen-(Ci-C6)-alkyl, Halogen-(Ci-C6)-alkoxy-halogen-(Ci-C6)-alkyl, Halogen-(C3-C7)-cycloalkoxy-(Ci-C6)- alkyl, (C3-C7)-Cycloalkenyloxy-(Ci-C6)-alkyl, Halogen-(C3-C7)-cycloalkenyloxy- (Ci-C6)-alkyl, Di-(Ci-C6)-alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl-carbonyl, (Ci-C6)-Alkoxy-carbonyl-(Ci-C6)-alkyl, Halogen-(Ci-C6)-alkoxy-carbonyl, (C1-C10)- Alkoxy, Halogen-(Ci-Cio)-alkoxy, (C3-Ci2)-Cycloalkoxy, Halogen-(C3-C7)-cycloalkoxy, (C3-C7)-Cycloalkyl-(Ci-C6)-alkoxy, (C2-Ci2)-Alkenyloxy, Halogen-(C2-Cio)-alkenyloxy, (C2-Cio)-Alkinyloxy, Halogen-(C3-Cio)-alkinyloxy, (Ci-C6)-alkoxy-(Ci-C6)-alkoxy, (C1- C6)-Alkyl-carbonyloxy, Halogen-(C2-Ci2)-alkyl-carbonyloxy, (C3-C7)-Cycloalkyl- carbonyloxy, (Ci-C6)-Alkyl-carbonyl-(Ci-C6)-alkoxy, (Ci-Cio)-Al kylthio, Halogen-(Ci- Cio)-alkylthio, (C3-Ci2)-Cycloalkylthio, (Ci-Cio)-Alkylsulfinyl, Halogen-(Ci-Cio)- alkylsulfinyl, (Ci-Cio)-alkylsulfonyl, Halogen-(Ci-Cio)-alkylsulfonyl, (C3-Ci2)- Cycloalkylsulfonyl, (Ci-C6)-Alkyl-carbonylthio, (Ci-C6)-Alkyl(thiocarbonyl)thio, (C3-Ci2)- Cycloalkylsulfinyl, (Ci-C6)-Alkylaminosulfonyl, Di-(Ci-C6)-alkylamino-sulfonyl, (C1-C6)- Alkylamino, Di-(Ci-C6)-alkylamino, Halogen-(Ci-C6)-alkylamino, Halogen-di-(Ci-C6)- alkylamino, (C3-Ci2)-Cycloalkylamino, (Ci-C6)-Alkyl-carbonylamino, Halogen-(Ci-C6)- alkyl-carbonylamino, (Ci-Cio)-Alkylsulfonylamino, Halogen-(Ci-Cio)-alkylsulfonylamino, (C3-C7)-Cycloalkyl-(Ci-C6)-alkyl-amino, Cyano, Hydroxy, Amino, C(=O)OH, (C 3 -C 7 ) -Cycloal koxycarbonyl, (C 3 -C 7 ) -Cycloal kyl- (Ci -C6) -al koxycarbonyl, (Ci-Ce) - alkylamino-carbonyl, di- (C C 6 ) -alkylaminocarbonyl, (C 3 -C 7 ) -cycloalkylaminocarbonyl, cyano- (C 1 -C 6 ) -alkyl, hydroxy- (C 1 -C 6 ) -alkyl, (C 3 -C 7 ) -cycloalkenyl- (C 3 -C 7 ) -cycloalkenyl- C 1 -C 6 ) -alkyl, halogen- (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy-halogeno (C 1 -C 6 ) -alkyl, halogenated C6) -alkoxy-halogeno (C 1 -C 6 ) -alkyl, halogeno (C 3 -C 7 ) -cycloalkoxy- (C 1 -C 6 ) -alkyl, (C 3 -C 7 ) -cycloalkenyloxy- (C 1 -C 6 ) alkyl, halo (C 3 -C 7 ) -cycloalkenyloxy- (C 1 -C 6 ) -alkyl, di- (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy (C 1 -C 6 ) -alkyl-carbonyl, (C 1 -C 6 ) -alkoxycarbonyl- (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkoxycarbonyl, (C 1 -C 10) -alkoxy, Halogeno (C 1 -C 10) -alkoxy, (C 3 -C 12) -cycloalkoxy, halo (C 3 -C 7 ) -cycloalkoxy, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 6 ) -alkoxy, ( C 2 -C 12) -alkenyloxy, halogeno (C 2 -C 10) -alkenyloxy, (C 2 -C 10) -alkynyloxy, halogeno (C 3 -C 10) -alkynyloxy, (C 1 -C 6) -alkoxy- (C 1 -C 6) - alkoxy, (C 1 -C 6) -alkyl-carbonyloxy, halogens n- (C 2 -C 12) -alkyl-carbonyloxy, (C 3 -C 7 ) -cycloalkyl-carbonyloxy, (C 1 -C 6) -alkyl-carbonyl- (C 1 -C 6 ) -alkoxy, (C 1 -C 10) -alkylthio , halo (Ci- Cio) alkylthio, (C 3 -C 2) cycloalkylthio, (Ci-Cio) alkylsulfinyl, halo (Ci-Cio) - alkylsulfinyl, (Ci-Cio) alkylsulfonyl, halo ( Ci-Cio) alkylsulfonyl, (C3 -Ci2) - cycloalkylsulfonyl, (Ci-C 6) alkyl-carbonylthio, (Ci-C 6) -alkyl (thiocarbonyl) thio, (C 3 -C 2) - cycloalkylsulfinyl, (C 1 -C 6) -alkylaminosulphonyl, di (C 1 -C 6) -alkylaminosulphonyl, (C 1 -C 6) -alkylamino, di- (C 1 -C 6) -alkylamino, halogeno (C 1 -C 6) -alkylamino, halogeno di- (C 1 -C 6) alkylamino, (C 3 -C 12) cycloalkylamino, (C 1 -C 6) alkylcarbonylamino, halo (C 1 -C 6) -alkylcarbonylamino, (C 1 -C 10) -alkylsulfonylamino, halogen (C 1 -C 10) -alkylsulfonylamino, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 6 ) -alkylamino, cyano, hydroxy, amino, C (OO) OH,
C(=O)NHOH, SO2NH2. SO2NHCN, SO2NHOH, NHCHO, G, W2G, oder C (= O) NHOH, SO 2 NH 2. SO 2 NHCN, SO 2 NHOH, NHCHO, G, W 2 G, or
R1 bedeutet Phenyl, Phenylsulfonyl, W1-(Phenyl), W1-(O-Phenyl), W1-(S-Phenyl), W1-(SO2-Phenyl), W2-(SO2CH2-Phenyl) oder W2-(SCH2-Phenyl), wobei die Phenylringe der acht vorstehend genannten Reste jeweils s Substituenten R6 tragen, oder X1 bedeutet N oder CR2a, R 1 is phenyl, phenylsulfonyl, W 1 - (phenyl), W 1 - (O-phenyl), W 1 - (S-phenyl), W 1 - (SO 2 -phenyl), W 2 - (SO 2 CH 2 -Phenyl) or W 2 - (SCH 2 -phenyl), wherein the phenyl rings of the eight radicals mentioned above each carry s substituents R 6 , or X 1 is N or CR 2a ,
X2 bedeutet N oder CR2b, R2a bedeutet Phenyl oder W3-(Phenyl), wobei die Phenylringe der zwei vorstehend genannten Reste jeweils s Substituenten R6 tragen, oder X 2 is N or CR 2b , R 2a is phenyl or W 3 - (phenyl), wherein the phenyl rings of the two radicals mentioned above each have s substituents R 6 , or
R2a bedeutet G, W4G, Wasserstoff, Cyano, Amino, Nitro, CHO, C(=O)OH, R 2a represents G, W 4 G, is hydrogen, cyano, amino, nitro, CHO, C (= O) OH,
C(=O)NH2, C(=S)NH2, C(=O)NHCN, C(=O)NHOH, SH, SO2NH2, SO2NHCN, C (= O) NH 2 , C (= S) NH 2 , C (= O) NHCN, C (= O) NHOH, SH, SO 2 NH 2 , SO 2 NHCN,
SO2NHOH, SF5, NHCHO, NHNH2, NHOH, NHCN, NHC(O)NH2, (Ci-Cio)-Alkyl, (C2- Cio)-Alkenyl, (C2-Cio)-Alkinyl, Halogen-(Ci-Cio)-alkyl, Halogen-(C2-Cio)-alkenyl,SO 2 NHOH, SF 5, NHCHO, NHNH 2, NHOH, NHCN, NHC (O) NH2, (Ci-Cio) alkyl, (C 2 - Cio) alkenyl, (C2 -Cio) alkynyl, halogen (C 1 -C 10) -alkyl, halogeno (C 2 -C 10) -alkenyl,
Halogen-(C2-Cio)-alkinyl, (C3-C8)-Cycloalkyl, Halogen-(C3-C8)-cycloalkyl, (Ci-Ce)-Alkyl- (C3-C7)-cycloal kyl , (C3-C7)-Cycloal kyl-(Ci -C6)-al kyl , (Ci -C6)-Cycloal kyl-(Ci -C6)- cycloalkyl, Halogen-(Ci-C6)-Cycloalkyl-(Ci-C6)-alkyl, (Ci-C6)-Alkyl-(C3-C7)-cycloalkyl- (Ci-C6)-alkyl, (C3-C8)-Cycloalkenyl, Halogen-(C3-C8)-Cycloalkenyl, (Ci-Ce)-Alkoxy (Ci- C6)-alkyl, (Ci-Ce)-Alkoxy (Ci-C6)-alkenyl, (Ci-C6)-Alkyl-(C3-C7)-cycloalkyl, (Ci-C6)- Al koxy-(C3-C7)-cycloal kyl , (Ci -C6)-Cycloal koxy-(Ci -C6)-al kyl , (C3-C7)-Cycloal koxy-(Ci- C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxy-(Ci-C6)-alkyl, (C2-C8)-Al ky Ith ioal ky I , (Ci-C6)- Alkylsulfinyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylsulfonyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylamino-(Ci- C6)-alkyl, Di-(Ci-C6)-alkylamino-(Ci-C6)-alkyl, Halogen-(Ci-C6)-alkylamino-(Ci-C6)- alkyl, (C3-C7)-Cycloalkylamino-(Ci-C6)-alkyl, (Ci-C6)-Alkyl-carbonyl, Halogen-(Ci-Ce)- alkyl-carbonyl, (C3-C7)-Cycloalkyl-carbonyl, (Ci-C6)-Alkoxy-carbonyl, (C3-C7)- Cycloalkoxy-carbonyl, (C3-C7)-Cycloalkyl-(Ci-C6)-alkoxy-carbonyl, (Ci-C6)-Alkylamino- carbonyl, Di-(Ci-C6)-alkyl-amino-carbonyl, (C3-C7)-Cycloalkyl-amino-carbonyl, Cyano- (Ci-C6)-alkyl, Hydroxy-(Ci-C6)-alkyl, (C3-C7)-Cycloalkenyl-(Ci-C6)-alkyl, Halogen-(Ci- C6)-alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-halogen-alkyl, Halogen-(Ci-Ce)- alkoxy-(Ci-C6)-halogen-alkyl, Halogen-(C3-C7)-cycloalkoxy-(Ci-C6)-alkyl, (C3-C7)- Cycloalkenyloxy-(Ci-C6)-alkyl, Halogen-(C3-C7)-cycloalkenyloxy-(Ci-C6)-alkyl, Di-(Ci- C6)-alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl-carbonyl, (Ci-C6)-Alkoxy- carbonyl-(Ci-C6)-alkyl, Halogen-(Ci-C6)-alkoxy-carbonyl, (Ci-C6)-Alkoxy, Halogen-(Ci- C6)-alkoxy, (C3-C8)-Cycloalkoxy, Halogen-(C3-C8)-cycloalkoxy, (C3-C7)-Cycloalkyl-(Ci- C6)-alkoxy, (C2-C6)-Alkenyloxy, Halogen-(C2-C6)-alkenyloxy, (C2-C6)-Alkinyloxy, Halogen-(C3-C6)-alkinyloxy, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxy, (Ci-C8)-Alkyl-carbonyloxy, Halogen-(Ci-C8)-alkylcarbonyloxy, (C3-C7)-Cycloalkyl-carbonyloxy, (Ci-Ce)-Alky- carbonyl-(Ci-C6)-alkoxy, (Ci-C6)-Alkylthio, Halogen-(Ci-C6)-alkylthio, (C3-C8)- Cycloalkylthio, (Ci -Ce)-Al ky Isulfinyl , Halogen-(Ci-C6)-alkylsulfinyl, (Ci-C6)-Alkylsulfonyl, Halogen-(Ci-C6)-alkylsulfonyl, (C3-Cio)-Cycloalkylsulfonyl, (Ci-C6)-Alkylcarbonylthio, (Ci-C6)-Alkyl(thiocarbonyl)thio, (C3-C8)-Cycloalkylsulfinyl, (Ci-C6)-Alkylaminosulfonyl, Di-(Ci-C6)-alkylaminosulfonyl, (Ci-C6)-Alkylamino, Di-(Ci-C6)-alkylamino, Halogen-(Ci- C6)-alkylamino, Halogen-di-(Ci-C6)-alkylamino, (C3-C8)-Cycloalkylamino, (C2-C8)-Halo (C 2 -C 10) -alkynyl, (C 3 -C 8 ) -cycloalkyl, halo (C 3 -C 8 ) -cycloalkyl, (C 1 -C 6 ) -alkyl (C 3 -C 7 ) -cycloal kyl, (C 3 -C 7 ) -cycloalkyl (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -cycloalkyl (C 1 -C 6 ) -cycloalkyl, halogeno (C 1 -C 6 ) - cycloalkyl- (Ci-C 6) alkyl, (Ci-C 6) -alkyl- (C 3 -C 7) cycloalkyl- (Ci-C 6) alkyl, (C 3 -C 8) cycloalkenyl, halogen - (C 3 -C 8) cycloalkenyl, (Ci-Ce) alkoxy (Ci- C6) alkyl, (Ci-Ce) alkoxy (Ci-C 6) alkenyl, (Ci-C 6) - Alkyl- (C 3 -C 7 ) -cycloalkyl, (C 1 -C 6 ) -alkoxy- (C 3 -C 7 ) -cycloalkyl, (C 1 -C 6 ) -cycloalkoxy (C 1 -C 6 ) - al kyl, (C 3 -C 7 ) -cycloalkoxy (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 2 -C 8 ) -Al ky Ith ioal ky I, (Ci-C 6 ) - alkylsulfinyl (Ci-C 6 ) alkyl, (Ci-C6) alkylsulfonyl (Ci-C 6 ) alkyl, (Ci -C 6) alkylamino (Ci- C6) alkyl, di (Ci-C6) alkylamino (Ci-C6) alkyl, halo (Ci-C6) alkylamino (Ci-C 6 ) - alkyl, (C 3 -C 7 ) -cycloalkylamino- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylcarbonyl, halogeno (C 1 -C 6 ) -alkylcarbonyl l, (C 3 -C 7) -cycloalkyl-carbonyl, (Ci-C6) alkoxy-carbonyl, (C 3 -C 7) - cycloalkoxy-carbonyl, (C 3 -C 7) cycloalkyl (Ci-C6 ) -alkoxycarbonyl, (C 1 -C 6 ) -alkylaminocarbonyl, di (C 1 -C 6 ) -alkyl-amino-carbonyl, (C 3 -C 7 ) -cycloalkyl-amino-carbonyl, cyano- (C 1 -C 4 -alkyl) 6 ) -alkyl, hydroxy (Ci-C 6 ) -alkyl, (C 3 -C 7 ) -cycloalkenyl- (Ci-C 6 ) -alkyl, halo (Ci- C 6 ) -alkoxy- (Ci-C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -haloalkyl, halogeno (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -haloalkyl, halogeno (C 3 -C 7 ) -cycloalkoxy- (C 1 -C 6 ) -alkyl, (C 3 -C 7 ) -cycloalkenyloxy- (C 1 -C 6 ) -alkyl, halogeno (C 3 -C 7 ) -cycloalkenyloxy- (C 1 -C 6 ) -alkyl , Di- (C 1 -C 6 ) alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl-carbonyl, (C 1 -C 6 ) -alkoxycarbonyl- ( C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkoxycarbonyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy, (C 3 -C 8 ) -cycloalkoxy, halogeno ( C 3 -C 8 ) -cycloalkoxy, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 6 ) -alkoxy, (C 2 -C 6) -alkenyloxy, halo (C 2 -C 6) -alkenyloxy, (C 2 -C 6) alkynyloxy, halogeno (C 3 -C 6) alkynyloxy, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkoxy, (C 1 -C 8 ) -alkyl-carbonyloxy, halogeno (C 1 -C 8 ) -alkylcarbonyloxy, (C 3 -C 7 ) -cycloalkyl-carbonyloxy, (Ci-Ce) -Alky- carbonyl- (Ci-C 6) alkoxy, (Ci-C 6) alkylthio, halo (Ci-C 6) -alkylthio, (C 3 -C 8) - Cycloalkylthio, (Ci -Ce) -Al ky Isulfinyl, halo (Ci-C6) alkylsulfinyl, (Ci-C 6) alkylsulfonyl, halo (Ci-C6) alkylsulfonyl, (C3-Cio) cycloalkylsulfonyl, (C 1 -C 6) -alkylcarbonylthio, (C 1 -C 6) -alkyl (thiocarbonyl) thio, (C 3 -C 8) -cycloalkylsulfinyl, (C 1 -C 6) -alkylaminosulfonyl, di- (C 1 -C 6) -alkylaminosulfonyl, (C 1 -C 6) ) -Alkylamino, di- (C 1 -C 6) -alkylamino, halogeno (C 1 -C 6) -alkylamino, halo-di- (C 1 -C 6) -alkylamino, (C 3 -C 8) -cycloalkylamino, (C 2 -C 8) -
Alkylcarbonylamino, Halogen-(C2-C8)-alkylcarbonylamino, (Ci-Cio)-Alkylsulfonylamino, Halogen-(Ci-Cio)-alkylsulfonylamino, (C3-C7)-Cycloalkyl-(Ci-C6)-alkyl-amino oder Halogen-tri-(Ci-C4)-alkylsilyl, bedeutet Wasserstoff, Halogen, (Ci-C4)-Alkyl oder (Ci-C4)-Alkoxy, 1 , Q2, Q3 oder Q4, Alkylcarbonylamino, halo (C 2 -C 8) -alkylcarbonylamino, (C 1 -C 10) -alkylsulfonylamino, halogeno (C 1 -C 10) -alkylsulfonylamino, (C 3 -C 7) -cycloalkyl- (C 1 -C 6) -alkylamino or halogeno tri- (C 1 -C 4 ) -alkylsilyl, denotes hydrogen, halogen, (C 1 -C 4 ) -alkyl or (C 1 -C 4 ) -alkoxy, 1, Q 2 , Q 3 or Q 4 ,
Figure imgf000046_0001
R3 bedeutet (Ci-C8)-Alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, wobei diese Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Cyano, Nitro, S(O)n- (Ci-C6)-Alkyl, (Ci-Ce)-Alkoxy, Halogen-(Ci-C6)-alkoxy, (C3-C6)-Cycloalkyl, Heteroaryl, Heterocydyl oder Phenyl substituiert sind, wobei die 4 letztgenannten Reste jeweils durch p Reste aus der Gruppe bestehend aus Methyl, Ethyl, Methoxy, Trifluormethyl, Cyano und Halogen substituiert sind, und wobei Heterocydyl n Oxogruppen trägt, oder R3 bedeutet Phenyl, das jeweils durch p Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, S(O)n- (Ci-C6)-Alkyl, (Ci-Ce)-Alkoxy, Halogen-(Ci-C6)-alkoxy und (Ci-C6)-Alkoxy-(Ci-C )-alkyl substituiert ist,
Figure imgf000046_0001
R 3 is (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, where these radicals are each represented by s radicals from the group consisting of halogen, cyano, nitro, S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy, (C 3 -C 6 ) -cycloalkyl, heteroaryl, heterocyclic or phenyl in which the 4 last-mentioned radicals are each substituted by p radicals from the group consisting of methyl, ethyl, methoxy, trifluoromethyl, cyano and halogen, and where heterocyclyl carries n oxo groups, or R 3 is phenyl, each being represented by p radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, S (O) n - (C 1 -C 6 ) - Alkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy and (C 1 -C 6 ) -alkoxy- (C 1 -C 4) -alkyl,
R4 bedeutet (Ci-C6)-Alkyl, (C3-C7)-cyclo-Alkyl, Halogen-(Ci-C6)-alkyl, (Ci-C6)- Alkoxy, Halogen-(Ci-C6)-alkoxy, Cyano, Nitro, Methylsulfenyl, Methylsulfinyl, R 4 is (Ci-C 6) -alkyl, (C 3 -C 7) -cycloalkyl, halo (Ci-C 6) alkyl, (Ci-C 6) - alkoxy, halo (Ci-C6 ) -alkoxy, cyano, nitro, methylsulfenyl, methylsulfinyl,
Methylsulfonyl, (Ci-C4)-Alkylcarbonylamino, Benzoylamino, Methoxycarbonyl, Methylsulfonyl, (C 1 -C 4 ) -alkylcarbonylamino, benzoylamino, methoxycarbonyl,
Ethoxycarbonyl, Benzoyl, Phenoxy, Methylcarbonyl, Piperidinylcarbonyl, Ethoxycarbonyl, benzoyl, phenoxy, methylcarbonyl, piperidinylcarbonyl,
Trifluormethylcarbonyl, Halogen, Amino, Aminocarbonyl, Methylaminocarbonyl, Dimethylanninocarbonyl, Methoxymethyl, 1 ,2,4-Triazol-1 -yl, Pyrazol-1 -yl, 2-Thiophenyl, 2-Pyridinyl, 3-Pyridinyl, 4-Pyridinyl, 1 ,2,4-Oxadiazol-3-yl, Benzoxazol-2-yl, 1 - Ethylbenzimidazol-2-yl, Piperidin-1 -yl oder jeweils durch p Reste aus der Gruppe bestehend aus Methyl, Ethyl, Methoxy, Trifluormethyl und Halogen substituiertes Phenyl, Trifluoromethylcarbonyl, halogen, amino, aminocarbonyl, methylaminocarbonyl, Dimethylanninocarbonyl, methoxymethyl, 1, 2,4-triazol-1-yl, pyrazol-1-yl, 2-thiophenyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 1, 2,4-oxadiazol-3-yl, Benzoxazol-2-yl, 1-ethylbenzimidazol-2-yl, piperidin-1-yl or phenyl each substituted by p radicals selected from the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen,
R5 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (C3-C7)-Cycloalkyl, Halogen-(Ci-C6)-alkyl, (C3-C7)-Cycloalkylmethyl, Methoxycarbonylmethyl, Ethoxycarbonylmethyl, R 5 represents hydrogen, (Ci-C 6) -alkyl, (C 3 -C 7) cycloalkyl, halo (Ci-C 6) alkyl, (C3-C7) cycloalkylmethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl,
Acetylmethyl, Methoxymethyl, Methoxyethyl, Benzyl, Pyrazin-2-yl, Furan-2-yl, Acetylmethyl, methoxymethyl, methoxyethyl, benzyl, pyrazine-2-yl, furan-2-yl,
Tetrahydrofuran-2-yl, Morpholin, Dimethylamino oder durch p Reste aus der Gruppe bestehend aus Methyl, Methoxy, Trifluormethyl und Halogen substituiertes Phenyl, Tetrahydrofuran-2-yl, morpholine, dimethylamino or phenyl substituted by p radicals from the group consisting of methyl, methoxy, trifluoromethyl and halogen,
R6 bedeutet Halogen, Cyano, Hydroxy, Amino, Nitro, -CHO, -C(=O)OH, R 6 is halogen, cyano, hydroxy, amino, nitro, -CHO, -C (= O) OH,
-C(=O)NH2, -C(=S)NH2, -C(=O)NHCN, -C(=O)NHOH, -SH, -SO2NH2, -SO2NHCN, -SO2NHOH, -OCN, -SCN, -SF5, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, -C (= O) NH 2 , -C (= S) NH 2 , -C (= O) NHCN, -C (= O) NHOH, -SH, -SO 2 NH 2 , -SO 2 NHCN, -SO 2 NHOH, -OCN, -SCN, -SF 5, (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl,
Halogen-(Ci-C6)-alkyl, Halogen-(C2-C6)-alkenyl, Halogen-(C2-C6)-alkinyl, (C3-C8)- Cycloalkyl, Halogen-(C3-C8)-cycloalkyl, (Ci-C6)-Alkyl-(C3-C7)-cycloalkyl, (C3-C7)- Cycloalkyl-(Ci-C6)-alkyl, (C3-C8)-Cycloalkenyl, Halogen-(C3-C8)-cycloalkenyl, (C1-C6)- Alkoxy-(Ci-C6)-alkyl, (C3-C7)-Cycloalkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxy- (Ci-C6)-alkyl, (Ci-C6)-Alkylthio-(Ci-C6)-alkyl, (Ci-C8)-Alkylsulfinyl-(Ci-C6)-alkyl, (Ci-C8)- Alkoxy-halogen-(Ci-C6)-alkyl, Cyano-(Ci-C6)-alkyl, Hydroxy-(Ci-C6)-alkyl, (Ci-C6)- Alkoxy, Halogen-(Ci-C6)-alkoxy, (C3-C8)-Cycloalkoxy, Halogen-(C3-C8)-cycloalkoxy, (C3-C8)-Cycloalkyl-(Ci-C6)-alkoxy, (C2-C6)-Alkenyloxy, Halogen-(C2-C6)-alkenyloxy, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxy, (C2-C6)-Alkylcarbonyloxy, (Ci-C6)-Alkylthio, Halogen- (Ci-C6)-alkylthio, (C3-C8)-Cycloalkylthio, (Ci-C6)-Alkylsulfinyl, Halogen-(Ci-C6)- alkylsulfinyl, (Ci-C6)-Alkylsulfonyl, Halogen-(Ci-C6)-alkylsulfonyl, (C3-C8)- Cycloalkylsulfonyl, (Ci-C6)-Alkylamino, Di-(Ci-C6)-alkylamino, Halogen-(Ci-C6)- alkylamino, Halogen-di-(Ci-C8)-alkylamino oder (C3-C8)-Cycloalkylamino, oder zwei vicinale Reste R6 bilden eine (C3-C6)-Alkylengruppe, in der p Kohlenstoffatome durch Sauerstoff, Schwefel oder Stickstoff ersetzt sind, und in der ein Kohlenstoffatom t Oxogruppen trägt, Halo (C 1 -C 6) alkyl, halo (C 2 -C 6) alkenyl, halo (C 2 -C 6) alkynyl, (C 3 -C 8) cycloalkyl, halo (C 3 -C 8 ) cycloalkyl , (Ci-C6) alkyl- (C3-C7) cycloalkyl, (C 3 -C 7) - cycloalkyl- (Ci-C6) alkyl, (C3-C8) cycloalkenyl, halo (C3-C8 ) -cycloalkenyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 3 -C 7 ) -cycloalkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 4) -alkyl C 6 ) alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -alkyl, (C 1 -C 8 ) -alkylsulfinyl- (C 1 -C 6 ) -alkyl, (Ci -C 8 ) - alkoxy-halo (C 1 -C 6 ) -alkyl, cyano- (C 1 -C 6 ) -alkyl, hydroxy (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, halogen - (C 1 -C 6) -alkoxy, (C 3 -C 8) -cycloalkoxy, halogeno (C 3 -C 8) -cycloalkoxy, (C 3 -C 8) -cycloalkyl- (C 1 -C 6) -alkoxy, (C 2 -C 6) - alkenyloxy, halo (C 2 -C 6) alkenyloxy, (Ci-C6) alkoxy (Ci-C6) alkoxy, (C 2 -C 6) alkylcarbonyloxy, (Ci-C 6) alkylthio, halo (C 1 -C 6 ) -alkylthio, (C 3 -C 8 ) -cycloalkylthio, (C 1 -C 6 ) -alkylsulfinyl, halogeno- (C 1 -C 6 ) -alkylsulfinyl, (C 1 -C 6 ) -alkylsulfonyl, halogen- C 1 -C 6 ) -alkylsulfonyl, (C 3 -C 8 ) -cycloalkylsulfone onyl, (C 1 -C 6) -alkylamino, di- (C 1 -C 6) -alkylamino, halogeno (C 1 -C 6) -alkylamino, halo-di- (C 1 -C 8) -alkylamino or (C 3 -C 8) -cycloalkylamino, or two vicinal radicals R 6 form a (C 3 -C 6 ) -alkylene group in which p carbon atoms are replaced by oxygen, sulfur or nitrogen, and in which a carbon atom carries t oxo groups,
Y bedeutet O, W1 bedeutet (Ci-Cio)-Alkylen, (C2-C6)-Alkenylen oder (C2-C6)-Alkinylen, Y is O, W 1 denotes (C 1 -C 10) -alkylene, (C 2 -C 6 ) -alkenylene or (C 2 -C 6 ) -alkynylene,
W2, W3 und W4 bedeuten jeweils (Ci-Cio)-Alkylen, W 2 , W 3 and W 4 are each (C 1 -C 10) -alkylene,
G bedeutet jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-C6)-Alkoxy, Halogen-(Ci-C6)-alkoxy und (Ci-C6)-Alkoxy-(Ci-C4)-alkyl substituiertes Heteroaryl oder Heterocyclyl, wobei Heterocyclyl n Oxogruppen trägt, n bedeutet 0, 1 oder 2, p bedeutet 0, 1 , 2 oder 3, s bedeutet 0, 1 , 2, 3, 4 oder 5, t bedeutet 0 oder 1 G represents in each case by s radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy and (C 1 -C 6 ) -alkoxy- (C 1 -C 4 ) -alkyl-substituted heteroaryl or heterocyclyl, where heterocyclyl carries n oxo groups, n denotes 0, 1 or 2, p denotes 0, 1, 2 or 3, s denotes 0, 1, 2, 3, 4 or 5, t denotes 0 or 1
3. Azin-2-on-3-carboxamide der Formel (I) oder deren Salze nach Anspruch 1 oder 2, worin 3. Azin-2-one-3-carboxamides of the formula (I) or salts thereof according to claim 1 or 2, wherein
R1 bedeutet (Ci-Cio)-Alkyl, (C2-Cio)-Alkenyl, (C2-Cio)-Alkinyl, Halogen-(Ci-Cio)- alkyl, Halogen-(C2-Cio)-alkenyl, Halogen-(C2-Cio)-alkinyl, (C3-Cio)-Cycloalkyl, Halogen- (C3-Cio)-cycloal kyl , (Ci -C )-Al kyl-(C3-C7)-cycloal kyl , (C3-C7)-Cycloal kyl-(Ci -C6)-al kyl , (C3-C7)-Cycloalkyl-(C3-C7)-cycloalkyl, Halogen-(C3-C7)-cycloalkyl-(Ci-C6)-alkyl, (Ci-C6)- Alkyl-(C3-C7)-cycloalkyl-(Ci-C6)-alkyl, (C3-Ci2)-Cycloalkenyl, Halogen-(C3-Ci2)- cycloalkenyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(C2-C6)-alkenyl, (Ci-C6)- Al kyl-(C3-C7)-cycloal kyl , (Ci -C6)-Al koxy-(C3-C7)-cycloal kyl , (C3-C7)-Cycloal koxy-(Ci - C6)-al kyl , (C3-C7)-Cycloal koxy-(Ci -C6)-al koxy-(Ci -C6)-al kyl , (Ci -C6)-Al koxy-(Ci -C6)- alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkylthio-(Ci-C6)-alkyl, (Ci-C6)-Alkylsulfinyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylsulfonyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylamino-(Ci-C6)-alkyl, Di-(Ci-Ce)- alkylamino-(Ci-C6)-alkyl, Halogen-(Ci-C6)-alkylamino-(Ci-C6)-alkyl, (C3-C7)- Cycloalkylamino-(Ci-C6)-alkyl, (Ci-C6)-Alkyl-carbonyl, Halogen-(Ci-C6)-alkyl-carbonyl, (C3-C7)-Cycloal kyl-carbonyl , (Ci -ΟΘ)-ΑΙ koxy-carbonyl , (C3-C7)-Cycloal koxy-carbonyl , (C3-C7)-Cycloalkyl-(Ci-C6)-alkoxy-carbonyl, (Ci-C6)-Alkylamino-carbonyl, Di-(Ci-Ce)- alkylamino-carbonyl, (C3-C7)-Cycloalkylamino-carbonyl, Cyano-(Ci-C6)-alkyl, Hydroxy- (Ci-C6)-alkyl, (C3-C7)-Cycloalkenyl-(Ci-C6)-alkyl, Halogen-(Ci-C6)-alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-halogen-(Ci-C6)-alkyl, Halogen-(Ci-C6)-alkoxy-halogen-(Ci-C6)-alkyl, Halogen-(C3-C7)-cycloalkoxy-(Ci-C6)-alkyl, (C3-C7)-Cycloalkenyloxy-(Ci-C6)-alkyl,R 1 represents (C 1 -C 10) -alkyl, (C 2 -C 10) -alkenyl, (C 2 -C 10) -alkynyl, halogeno (C 1 -C 10) -alkyl, halogeno (C 2 -C 10) -alkenyl, halogen (C 2 -C 10) -alkynyl, (C 3 -C 10) -cycloalkyl, halogeno (C 3 -C 10) -cycloalkyl, (C 1 -C 6 ) -alkyl (C 3 -C 7 ) -cycloalkyl, ( C 3 -C 7 ) -cycloalkyl (C 1 -C 6 ) -alkyl, (C 3 -C 7 ) -cycloalkyl- (C 3 -C 7 ) -cycloalkyl, halogeno (C 3 -C 7 ) -cycloalkyl - (Ci-C 6) alkyl, (Ci-C6) - alkyl- (C3-C7) cycloalkyl- (Ci-C 6) alkyl, (C3-Ci2) cycloalkenyl, halo ( C 3 -C 2 ) - cycloalkenyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 2 -C 6 ) -alkenyl, (C 1 -C 6 ) - Al kyl- (C 3 -C 7 ) -cycloal kyl, (Ci -C 6 ) -Al koxy- (C 3 -C 7 ) -cycloal kyl, (C 3 -C 7 ) -Cycloal koxy- (Ci - C 6 ) -alkenyl, (C 3 -C 7 ) -cycloalkoxy (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylsulfinyl- (C 1 -C 6 ) -alkyl, ( C 1 -C 6 ) -alkylsulfonyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylamino- (C 1 -C 6 ) -alkyl, di (C 1 -C 6 ) -alkylamino- (C 1 -C 6 ) -al kyl, halo (C 1 -C 6) -alkylamino (C 1 -C 6) -alkyl, (C 3 -C 7 ) -cycloalkylamino (C 1 -C 6) -alkyl, (C 1 -C 6) -alkylcarbonyl, halogeno ( C 1 -C 6) -alkyl-carbonyl, (C 3 -C 7 ) -cycloalkylcarbonyl, (C 1 -C 4) -alkoxy-carbonyl, (C 3 -C 7 ) -cycloalkoxy-carbonyl, (C 3 -C 7) -cycloalkyl- (C 1 -C 6) -alkoxycarbonyl, (C 1 -C 6) -alkylamino-carbonyl, di- (C 1 -C 6) -alkylaminocarbonyl, (C 3 -C 7) -cycloalkylamino-carbonyl, Cyano- (C 1 -C 6 ) -alkyl, hydroxy- (C 1 -C 6 ) -alkyl, (C 3 -C 7 ) -cycloalkenyl- (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkoxy- ( C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy-halogeno (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkoxy-halogeno (C 1 -C 6 ) -alkyl, halogeno (C 3 -C 7) cycloalkoxy (Ci-C6) alkyl, (C3-C 7) -Cycloalkenyloxy- (Ci-C6) alkyl,
Halogen-(C3-C7)-cycloalkenyloxy-(Ci-C6)-alkyl, Di-(Ci-C6)-alkoxy-(Ci-C6)-alkyl, (Ci-C6)- Alkoxy-(Ci-C6)-alkyl-carbonyl, (Ci-C6)-Alkoxy-carbonyl-(Ci-C6)-alkyl, Halogen-(Ci-C6)- alkoxy-carbonyl, (Ci-Cio)-Alkoxy, Halogen-(Ci-Cio)-alkoxy, (C3-Ci2)-Cycloalkoxy, Halogen-(C3-C7)-cycloalkoxy, (C3-C7)-Cycloalkyl-(Ci-C6)-alkoxy, (C2-Ci2)-Alkenyloxy, Halogen-(C2-Cio)-alkenyloxy, (C2-Cio)-Alkinyloxy, Halogen-(C3-Cio)-alkinyloxy, (C1-C6)- alkoxy-(Ci-C6)-alkoxy, (Ci-C6)-Alkyl-carbonyloxy, Halogen-(C2-Ci2)-alkyl-carbonyloxy, (C3-C7)-Cycloal kyl-carbonyloxy, (Ci -ΟΘ)-ΑΙ kyl-carbonyl-(Ci -C6)-al koxy, (Ci -C10)- Alkylthio, Halogen-(Ci-Cio)-alkylthio, (C3-Ci2)-Cycloalkylthio, (Ci-Cio)-Alkylsulfinyl, Halogen-(Ci-Cio)-alkylsulfinyl, (Ci-Cio)-alkylsulfonyl, Halogen-(Ci-Cio)-alkylsulfonyl, (C3-Ci2)-Cycloalkylsulfonyl, (Ci-C6)-Alkyl-carbonylthio, (Ci-C6)-Alkyl(thiocarbonyl)thio, (C3-Ci2)-Cycloalkylsulfinyl, (Ci-C6)-Alkylaminosulfonyl, Di-(Ci-C6)-alkylamino-sulfonyl, (Ci-C6)-Alkylamino, Di-(Ci-C6)-alkylamino, Halogen-(Ci-C6)-alkylamino, Halogen-di- (Ci-C6)-alkylamino, (C3-Ci2)-Cycloalkylamino, (Ci-C6)-Alkyl-carbonylamino, Halogen- (Ci-C6)-alkyl-carbonylamino, (Ci-Cio)-Alkylsulfonylamino, Halogen-(Ci-Cio)- alkylsulfonylamino, (C3-C7)-Cycloalkyl-(Ci-C6)-alkyl-amino, Cyano, Hydroxy, Amino, C(=O)OH, C(=O)NHOH, SO2NH2. SO2NHCN, SO2NHOH, NHCHO, G, oder Halo (C3-C 7) -cycloalkenyloxy- (Ci-C 6) alkyl, di (Ci-C6) alkoxy (Ci-C 6) alkyl, (Ci-C6) - alkoxy- (Ci -C 6) -alkyl-carbonyl, (C 1 -C 6) -alkoxycarbonyl- (C 1 -C 6) -alkyl, halogeno (C 1 -C 6) -alkoxycarbonyl, (C 1 -C 10) -alkoxy, halogeno (Ci -C) alkoxy, (C 3 -C 12) -cycloalkoxy, halogeno (C 3 -C 7 ) -cycloalkoxy, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 6 ) -alkoxy, (C 2 -C 12) -alkenyloxy, Halogen (C 2 -C 10) alkenyloxy, (C 2 -C 10) -alkynyloxy, halogeno (C 3 -C 10) -alkynyloxy, (C 1 -C 6) -alkoxy- (C 1 -C 6) -alkoxy, (C 1 -C 6) - Alkyl-carbonyloxy, halogeno (C 2 -C 12) -alkyl-carbonyloxy, (C 3 -C 7 ) -cycloalkyl-carbonyloxy, (C 1 -C 4) -cyclocarbonyl- (C 1 -C 6) -alkoxy, (Ci -C10) - alkylthio, halogeno (Ci-Cio) -alkylthio, (C 3 -Ci 2) -cycloalkylthio, (Ci-Cio) -alkylsulfinyl, halo (Ci-Cio) -alkylsulfinyl, (Ci-Cio) -alkylsulfonyl , Halo (C 1 -C 10) -alkylsulfonyl, (C 3 -C 12) -cycloalkylsulfonyl, (C 1 -C 6 ) -alkylcarbonylthio, (C 1 -C 6 ) -alkyl (thiocarbonyl) thio, (C 3 -C 12) - Cycloalkylsulfinyl, (Ci-C6) -alkylaminosulfonyl, di- (Ci-C6) -alkylamino-sulfonyl, (Ci-C6) -Alkylami no, di- (C 1 -C 6) -alkylamino, halogeno (C 1 -C 6) -alkylamino, halo-di- (C 1 -C 6) -alkylamino, (C 3 -C 12) -cycloalkylamino, (C 1 -C 6) -alkyl- carbonylamino, halo (C 1 -C 6) alkylcarbonylamino, (C 1 -C 10) -alkylsulfonylamino, halo (C 1 -C 10) -alkylsulfonylamino, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 6) -alkylamino , Cyano, hydroxy, amino, C (= O) OH, C (= O) NHOH, SO 2 NH 2 . SO 2 NHCN, SO 2 NHOH, NHCHO, G, or
R1 bedeutet Phenyl, W1-(Phenyl), wobei die Phenylringe jeweils s Substituenten R6 tragen, X1 bedeutet N oder CR2a, X2 bedeutet N oder CR2b, R 1 is phenyl, W 1 - (phenyl), where the phenyl rings each carry s substituents R 6 , X 1 is N or CR 2a , X 2 is N or CR 2b ,
R2a bedeutet Phenyl oder W3-(Phenyl), wobei die Phenylringe der zwei vorstehend genannten Reste jeweils s Substituenten R6 tragen, oder R 2a is phenyl or W 3 - (phenyl), wherein the phenyl rings of the two radicals mentioned above each carry s substituents R 6 , or
R2a bedeutet G, W4G, Wasserstoff, Cyano, Amino, Nitro, CHO, C(=O)OH, R 2a represents G, W 4 G, is hydrogen, cyano, amino, nitro, CHO, C (= O) OH,
C(=O)NH2, C(=S)NH2, C(=O)NHCN, C(=O)NHOH, SH, SO2NH2, SO2NHCN, C (= O) NH 2 , C (= S) NH 2 , C (= O) NHCN, C (= O) NHOH, SH, SO 2 NH 2 , SO 2 NHCN,
SO2NHOH, SF5, NHCHO, NHNH2, NHOH, NHCN, NHC(O)NH2, (Ci-Cio)-Alkyl, (C2- Cio)-Alkenyl, (C2-Cio)-Alkinyl, Halogen-(Ci-Cio)-alkyl, Halogen-(C2-Cio)-alkenyl, Halogen-(C2-Cio)-alkinyl, (C3-C8)-Cycloalkyl, Halogen-(C3-C8)-cycloalkyl, (Ci-Ce)-Alkyl- (C3-C7)-cycloal kyl , (C3-C7)-Cycloal kyl-(Ci -C6)-al kyl , (Ci -C6)-Cycloal kyl-(Ci -C6)- cycloalkyl, Halogen-(Ci-C6)-Cycloalkyl-(Ci-C6)-alkyl, (Ci-C6)-Alkyl-(C3-C7)-cycloalkyl- (Ci-C6)-alkyl, (C3-C8)-Cycloalkenyl, Halogen-(C3-C8)-Cycloalkenyl, (Ci-Ce)-Alkoxy (Ci- C6)-alkyl, (Ci-Ce)-Alkoxy (Ci-C6)-alkenyl, (Ci-C6)-Alkyl-(C3-C7)-cycloalkyl, (Ci-C6)- Al koxy-(C3-C7)-cycloal kyl , (Ci -C6)-Cycloal koxy-(Ci -C6)-al kyl , (C3-C7)-Cyclo-al koxy-(Ci - C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxy-(Ci-C6)-alkyl, (C2-C8)-Al ky Ith ioal ky I , (Ci-C6)- Alkylsulfinyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylsulfonyl-(Ci-C6)-alkyl, (Ci-C6)-Alkyl-amino-(Ci- C6)-alkyl, Di-(Ci-C6)-alkylamino-(Ci-C6)-alkyl, Halogen-(Ci-C6)-alkylamino-(Ci-C6)- alkyl, (C3-C7)-Cycloalkylamino-(Ci-C6)-alkyl, (Ci-C6)-Alkyl-carbonyl, Halogen-(Ci-Ce)- alkyl-carbonyl, (C3-C7)-Cycloalkyl-carbonyl, (Ci-C6)-Alkoxy-carbonyl, (C3-C7)- Cycloalkoxy-carbonyl, (C3-C7)-Cycloalkyl-(Ci-C6)-alkoxy-carbonyl, (Ci-C6)-Alkylamino- carbonyl, Di-(Ci-C6)-alkyl-amino-carbonyl, (C3-C7)-Cycloalkyl-amino-carbonyl, Cyano- (Ci-C6)-alkyl, Hydroxy-(Ci-C6)-alkyl, (C3-C7)-Cycloalkenyl-(Ci-C6)-alkyl, Halogen-(Ci- C6)-alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-halogen-alkyl, Halogen-(Ci-Ce)- alkoxy-(Ci-C6)-halogen-alkyl, Halogen-(C3-C7)-cycloalkoxy-(Ci-C6)-alkyl, (C3-C7)- Cycloalkenyloxy-(Ci-C6)-alkyl, Halogen-(C3-C7)-cycloalkenyloxy-(Ci-C6)-alkyl, Di-(Ci- C6)-alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl-carbonyl, (Ci-Ce)-Alkoxy- carbonyl-(Ci-C6)-alkyl, Halogen-(Ci-C6)-alkoxy-carbonyl, (Ci-C6)-Alkoxy, Halogen-(Ci- C6)-alkoxy, (C3-C8)-Cycloalkoxy, Halogen-(C3-C8)-cycloalkoxy, (C3-C7)-Cycloalkyl-(Ci- c6)-alkoxy, (C2-C6)-Alkenyloxy, Halogen-(C2-C6)-alkenyloxy, (C2-C6)-Alkinyloxy, Halogen-(C3-C6)-alkinyloxy, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxy, (Ci-C8)-Alkyl-carbonyloxy, Halogen-(Ci-C8)-alkylcarbonyloxy, (C3-C7)-Cycloalkyl-carbonyloxy, (Ci-Ce)-Alky- carbonyl-(Ci-C6)-alkoxy, (Ci-C6)-Alkylthio, Halogen-(Ci-C6)-alkylthio, (C3-C8)-Cyclo- alkylthio, (Ci-C6)-Alkylsulfinyl, Halogen-(Ci-C6)-alkylsulfinyl, (Ci-C6)-Alkylsulfonyl, Halogen-(Ci-C6)-alkylsulfonyl, (C3-Cio)-Cycloalkylsulfonyl, (Ci-C6)-Alkylcarbonylthio, (Ci-C6)-Alkyl(thiocarbonyl)thio, (C3-C8)-Cycloalkylsulfinyl, (Ci-C6)-Alkylaminosulfonyl, Di-(Ci-C6)-alkylaminosulfonyl, (Ci-C6)-Alkylamino, Di-(Ci-C6)-alkylamino, Halogen-(Ci- C6)-alkylamino, Halogen-di-(Ci-C6)-alkylamino, (C3-C8)-Cycloalkylamino, (C2-C8)- Alkylcarbonylannino, Halogen-(C2-C8)-alkylcarbonylamino, (Ci-Cio)-Alkylsulfonylamino, Halogen-(Ci-Cio)-alkylsulfonylamino, (C3-C7)-Cycloalkyl-(Ci-C6)-alkyl-amino oder Halogen-tri-(Ci-C4)-alkylsilyl, bedeutet Wasserstoff, Halogen, (Ci-C4)-Alkyl oder (Ci-C4)-Alkoxy, Q bedeutet einen Rest Q1 , Q2, Q3 oder Q4 SO2NHOH, SF 5, NHCHO, NHNH 2, NHOH, NHCN, NHC (O) NH2, (Ci-Cio) alkyl, (C 2 - Cio) alkenyl, (C2 -Cio) alkynyl, halo ( C 1 -C 10) -alkyl, halogeno (C 2 -C 10) -alkenyl, Halo (C 2 -C 10) -alkynyl, (C 3 -C 8 ) -cycloalkyl, halo (C 3 -C 8 ) -cycloalkyl, (C 1 -C 6 ) -alkyl (C 3 -C 7 ) -cycloal kyl, (C 3 -C 7 ) -cycloalkyl (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -cycloalkyl (C 1 -C 6 ) -cycloalkyl, halogeno (C 1 -C 6 ) - cycloalkyl- (Ci-C 6) alkyl, (Ci-C 6) -alkyl- (C 3 -C 7) cycloalkyl- (Ci-C 6) alkyl, (C 3 -C 8) cycloalkenyl, halogen - (C 3 -C 8) cycloalkenyl, (Ci-Ce) alkoxy (Ci- C6) alkyl, (Ci-Ce) alkoxy (Ci-C 6) alkenyl, (Ci-C 6) - Alkyl- (C 3 -C 7 ) -cycloalkyl, (C 1 -C 6 ) -alkoxy- (C 3 -C 7 ) -cycloalkyl, (C 1 -C 6 ) -cycloalkoxy (C 1 -C 6 ) - al kyl, (C 3 -C 7) -cycloalkyl al alkoxy- (Ci - C 6) alkyl, (Ci-C6) alkoxy (Ci-C6) alkoxy (Ci-C 6) alkyl, (C 2 -C 8) -alkyl ky Ith ioal ky I, (Ci-C 6) - alkylsulfinyl (Ci-C 6) alkyl, (Ci-C6) alkylsulfonyl (Ci-C 6) alkyl, (C 1 -C 6 ) -alkylamino (C 1 -C 6 ) -alkyl, di (C 1 -C 6 ) -alkylamino (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkylamino ( Ci-C 6) - alkyl, (C 3 -C 7) cycloalkylamino (Ci-C 6) alkyl, (Ci-C 6) -alkyl-carbonyl, halo (Ci-Ce) - alkyl-ca rbonyl, (C 3 -C 7) -cycloalkyl-carbonyl, (Ci-C6) alkoxy-carbonyl, (C 3 -C 7) - cycloalkoxy-carbonyl, (C 3 -C 7) cycloalkyl (Ci-C6 ) -alkoxycarbonyl, (C 1 -C 6 ) -alkylaminocarbonyl, di (C 1 -C 6 ) -alkyl-amino-carbonyl, (C 3 -C 7 ) -cycloalkyl-amino-carbonyl, cyano- (C 1 -C 4 -alkyl) 6 ) -alkyl, hydroxy (Ci-C 6 ) -alkyl, (C 3 -C 7 ) -cycloalkenyl- (Ci-C 6 ) -alkyl, halo (Ci- C 6 ) -alkoxy- (Ci-C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -haloalkyl, halogeno (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -haloalkyl, halogeno (C 3 -C 7 ) -cycloalkoxy- (C 1 -C 6 ) -alkyl, (C 3 -C 7 ) -cycloalkenyloxy- (C 1 -C 6 ) -alkyl, halogeno (C 3 -C 7 ) -cycloalkenyloxy- (C 1 -C 6 ) -alkyl , Di- (C 1 -C 6 ) alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl-carbonyl, (C 1 -C 6 ) -alkoxycarbonyl- ( C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkoxycarbonyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy, (C 3 -C 8 ) -cycloalkoxy, halogeno ( C 3 -C 8 ) -cycloalkoxy, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 6 ) -alkoxy, (C 2 -C 6 ) -alkenyloxy, halogeno (C 2 -C 6 ) -alkenyloxy, (C 2 -C 6 ) Alkynyloxy, halo (C 3 -C 6) alkynyloxy, ( C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkoxy, (C 1 -C 8 ) -alkyl-carbonyloxy, halogeno (C 1 -C 8 ) -alkylcarbonyloxy, (C 3 -C 7 ) -cycloalkyl-carbonyloxy, ( Ci-Ce) -Alky- (carbonyl- (Ci-C 6) alkoxy, (Ci-C 6) alkylthio, halo Ci-C 6) -alkylthio, (C 3 -C 8) cyclo- alkylthio, (C 1 -C 6 ) -alkylsulfinyl, halogeno (C 1 -C 6 ) -alkylsulfinyl, (C 1 -C 6 ) -alkylsulfonyl, halogeno (C 1 -C 6 ) -alkylsulfonyl, (C 3 -C 10) -cycloalkylsulfonyl, (Ci -C 6) -alkylcarbonylthio, (C 1 -C 6 ) -alkyl (thiocarbonyl) thio, (C 3 -C 8 ) -cycloalkylsulfinyl, (C 1 -C 6 ) -alkylaminosulfonyl, di- (C 1 -C 6 ) -alkylaminosulfonyl, (C 1 -C 6 ) -alkyl ) -Alkylamino, di- (Ci-C6) -alkylamino, halo (Ci- C6) -alkylamino, halo-di- (Ci-C6) -alkylamino, (C 3 -C 8 ) -cycloalkylamino, (C2-C 8) - Alkylcarbonylannino, halo (C2-C8) alkylcarbonylamino, (Ci-Cio) alkylsulfonylamino, halo (Ci-Cio) alkylsulfonylamino, (C 3 -C 7) cycloalkyl (Ci-C6) - alkyl-amino or halo-tri (C 1 -C 4 ) -alkylsilyl, denotes hydrogen, halogen, (C 1 -C 4 ) -alkyl or (C 1 -C 4 ) -alkoxy, Q is a radical Q 1 , Q 2 , Q 3 or Q 4
Figure imgf000051_0001
Figure imgf000051_0001
R3 bedeutet jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Cyano, Nitro, S(0)n-(Ci-C6)-Alkyl, (Ci-C6)-Alkoxy und Halogen-(Ci-C6)-alkoxy substituiertes (Ci-C8)-Alkyl, (C2-C8)-Alkenyl oder (C2-C8)-Alkinyl, R4 bedeutet (Ci-C6)-Alkyl, (C3-C7)-cyclo-Alkyl, Halogen-(Ci-C6)-alkyl, (Ci-C6)- Alkoxy, Halogen-(Ci-C6)-alkoxy, Cyano, Nitro, Methylsulfenyl, Methylsulfinyl, R 3 represents in each case by s radicals from the group consisting of halogen, cyano, nitro, S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy and halogen- (C 1 -C 6 ) - alkoxy substituted (Ci-C 8) alkyl, (C 2 -C 8) alkenyl or (C2-C8) alkynyl, R 4 is (Ci-C 6) -alkyl, (C3-C7) -cyclo Alkyl, halo (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy, cyano, nitro, methylsulfenyl, methylsulfinyl,
Methylsulfonyl, (Ci-C4)-Alkylcarbonylamino, Benzoylamino, Methoxycarbonyl, Methylsulfonyl, (C 1 -C 4 ) -alkylcarbonylamino, benzoylamino, methoxycarbonyl,
Ethoxycarbonyl, Benzoyl, Phenoxy, Methylcarbonyl, Piperidinylcarbonyl, Ethoxycarbonyl, benzoyl, phenoxy, methylcarbonyl, piperidinylcarbonyl,
Trifluormethylcarbonyl, Halogen, Amino, Aminocarbonyl, Methylaminocarbonyl, Dimethylanninocarbonyl, Methoxymethyl, 1 ,2,4-Triazol-1 H, 1 -Pyrazol-1 H, 2-Thiophenyl, 2-Pyridinyl, 3-Pyridinyl, 4-Pyridinyl, 1 ,2,4-Oxadiazol-3-yl, Benzoxazol-2-yl, 1 - Ethylbenzimidazol-2-yl, Piperidin-1 -yl oder jeweils durch s Reste aus der Gruppe bestehend aus Methyl, Ethyl, Methoxy, Trifluormethyl und Halogen substituiertes Phenyl, Trifluoromethylcarbonyl, halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylanninocarbonyl, methoxymethyl, 1, 2,4-triazole-1H, 1-pyrazole-1H, 2-thiophenyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 1, 2,4-oxadiazol-3-yl, benzoxazol-2-yl, 1-ethylbenzimidazol-2-yl, piperidin-1-yl or phenyl substituted by s radicals selected from the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen .
R5 bedeutet Wassetrstoff, (Ci-C6)-Alkyl, (C3-C7)-Cycloalkyl, Halogen-(Ci-C6)- alkyl, (C3-C7)-Cycloalkylmethyl, Methoxycarbonylmethyl, Ethoxycarbonylmethyl, Acetylmethyl, Methoxymethyl, Methoxyethyl, Benzyl, Pyrazin-2-yl, Furan-2-yl, R 5 represents Wassetrstoff, (Ci-C 6) -alkyl, (C 3 -C 7) cycloalkyl, halo (Ci-C 6) - alkyl, (C3-C7) cycloalkylmethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, acetylmethyl, Methoxymethyl, methoxyethyl, benzyl, pyrazine-2-yl, furan-2-yl,
Tetrahydrofuran-2-yl, Morpholin, Dimethylamino oder durch p Reste aus der Gruppe bestehend aus Methyl, Methoxy, Trifluormethyl und Halogen substituiertes Phenyl, Tetrahydrofuran-2-yl, morpholine, dimethylamino or phenyl substituted by p radicals from the group consisting of methyl, methoxy, trifluoromethyl and halogen,
R6 bedeutet Halogen, Cyano, Nitro, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, (Ci-Ce)-Alkoxy, Halogen-(Ci-C6)-alkoxy, (Ci- Ce)-Al kylthio, (Ci-Ce)-Al kylsulfinyl, (Ci-CeJ-Alkylsulfonyl, Phenyl, Methylendioxo, Y bedeutet O, R 6 is halogen, cyano, nitro, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, halogeno (C 1 -C 6 ) -alkyl, (C 3 -C 4 ) -alkyl, C 6 ) -cycloalkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkylthio, (C 1 -C 6 ) -alkylsulfinyl, (C 1 -C 6 -alkylsulfonyl, Phenyl, methylene dioxo, Y is O,
W1 bedeutet (Ci-Cio)-Alkylen, W2, W3 und W4 bedeuten jeweils (Ci-Cio)-Alkylen, W 1 is (C 1 -C 10) -alkylene, W 2 , W 3 and W 4 are each (C 1 -C 10) -alkylene,
G bedeutet jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C3)-alkyl, Cyclopropyl, S(O)n-(Ci-C3)-Alkyl, (Ci-C )- Alkoxy, Halogen-(Ci-C4)-alkoxy und (Ci-C4)-Alkoxy-(Ci-C4)-alkyl substituiertes G is in each case represented by s radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 3 ) -alkyl, cyclopropyl, S (O) n - (C 1 -C 3 ) -Alkyl, (Ci-C) - alkoxy, halogen- (Ci-C 4 ) -alkoxy and (Ci-C 4 ) -alkoxy- (Ci-C 4 ) -alkyl substituted
Heteroaryl oder Heterocyclyl, wobei Heterocyclyl n Oxogruppen trägt, n bedeutet 0, 1 oder 2, p bedeutet 0, 1 , 2 oder 3, s bedeutet 0, 1 , 2, 3, 4 oder 5. Heteroaryl or heterocyclyl, wherein heterocyclyl carries n oxo groups, n means 0, 1 or 2, p means 0, 1, 2 or 3, s means 0, 1, 2, 3, 4 or 5.
4. Herbizide Mittel, gekennzeichnet durch einen herbizid wirksamen Gehalt an mindestens einer Verbindung der Formel (I) gemäß einem der Ansprüche 1 bis 3. 4. A herbicidal composition, characterized by a herbicidally active content of at least one compound of the formula (I) according to one of claims 1 to 3.
5. Herbizide Mittel nach Anspruch 4 in Mischung mit Formulierungshilfsmitteln. 5. A herbicidal composition according to claim 4 in admixture with formulation auxiliaries.
6. Herbizide Mittel nach Anspruch 4 oder 5 enthaltend mindestens einen weiteren pestizid wirksamen Stoff aus der Gruppe Insektizide, Akarizide, Herbizide, Fungizide,6. A herbicidal composition according to claim 4 or 5 containing at least one further pesticidal substance from the group insecticides, acaricides, herbicides, fungicides,
Safener und Wachstumsregulatoren. Safeners and growth regulators.
7. Herbizide Mittel nach Anspruch 6 enthaltend einen Safener. 7. A herbicidal composition according to claim 6 containing a safener.
8. Herbizide Mittel nach Anspruch 7 enthaltend cyprosulfamid, cloquintocet-mexyl, mefenpyr-diethyl oder isoxadifen-ethyl. 8. A herbicidal composition according to claim 7 containing cyprosulfamide, cloquintocet-mexyl, mefenpyr-diethyl or isoxadifen-ethyl.
9. Herbizide Mittel nach einem der Ansprüche 4 bis 8 enthaltend ein weiteres Herbizid. 9. A herbicidal composition according to any one of claims 4 to 8 containing a further herbicide.
10. Verfahren zur Bekämpfung unerwünschter Pflanzen, dadurch gekennzeichnet, daß man eine wirksame Menge mindestens einer Verbindung der Formel (I) gemäß einem der Ansprüche 1 bis 3 oder eines herbiziden Mittels nach einem der Ansprüche 4 bis 8 auf die Pflanzen oder auf den Ort des unerwünschten Pflanzenwachstums appliziert. 10. A method for controlling undesirable plants, characterized in that an effective amount of at least one compound of formula (I) according to any one of claims 1 to 3 or a herbicidal composition according to any one of claims 4 to 8 on the plants or on the place of unwanted plant growth applied.
1 1 . Verwendung von Verbindungen der Formel (I) gemäß einem der Ansprüche 1 bis 3 oder von herbiziden Mitteln nach einem der Ansprüche 4 bis 8 zur Bekämpfung unerwünschter Pflanzen. 1 1. Use of compounds of the formula (I) according to one of claims 1 to 3 or of herbicidal agents according to any one of claims 4 to 8 for controlling unwanted plants.
12. Verwendung nach Anspruch 1 1 , dadurch gekennzeichnet, daß die 12. Use according to claim 1 1, characterized in that the
Verbindungen der Formel (I) zur Bekämpfung unerwünschter Pflanzen in Kulturen von Nutzpflanzen eingesetzt werden. Compounds of formula (I) for controlling undesirable plants in crops of crops are used.
13. Verwendung nach Anspruch 12, dadurch gekennzeichnet, daß die Nutzpflanzen transgene Nutzpflanzen sind. 13. Use according to claim 12, characterized in that the crops are transgenic crops.
PCT/EP2014/064985 2013-07-16 2014-07-11 Azin-2-one-3-carboxamides and their use as herbicides WO2015007662A1 (en)

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Publication number Priority date Publication date Assignee Title
WO2017042259A1 (en) 2015-09-11 2017-03-16 Bayer Cropscience Aktiengesellschaft Hppd variants and methods of use
US10125138B2 (en) 2015-02-27 2018-11-13 Syngenta Participations Ag Triazolotriazinone derivatives having activity a s herbicides
US11180770B2 (en) 2017-03-07 2021-11-23 BASF Agricultural Solutions Seed US LLC HPPD variants and methods of use

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WO2012148622A1 (en) * 2011-04-28 2012-11-01 E. I. Du Pont De Nemours And Company Herbicidal pyrazinones
EP2562174A1 (en) * 2011-08-24 2013-02-27 Bayer Cropscience AG Herbicidal 6-Oxo-1,6-dihydropyrimidin-5-carboxamides and 2-Oxo-1,2-dihydropyridin-3-carboxamides

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WO2012148622A1 (en) * 2011-04-28 2012-11-01 E. I. Du Pont De Nemours And Company Herbicidal pyrazinones
EP2562174A1 (en) * 2011-08-24 2013-02-27 Bayer Cropscience AG Herbicidal 6-Oxo-1,6-dihydropyrimidin-5-carboxamides and 2-Oxo-1,2-dihydropyridin-3-carboxamides

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10125138B2 (en) 2015-02-27 2018-11-13 Syngenta Participations Ag Triazolotriazinone derivatives having activity a s herbicides
WO2017042259A1 (en) 2015-09-11 2017-03-16 Bayer Cropscience Aktiengesellschaft Hppd variants and methods of use
US11180770B2 (en) 2017-03-07 2021-11-23 BASF Agricultural Solutions Seed US LLC HPPD variants and methods of use

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