CN100502655C - Selective insecticides and/or acaricides based on substituted cyclic dicarbonyl compounds and safeners - Google Patents

Abstract

The invention relates to the use of selective insecticidal and/or acaricidal agents for controlling insects and/or arachnids. Said insecticidal and/or acaricidal agents are characterized by an active moiety of an active substance combination comprising (a) at least one substituted, cyclic dicarbonyl compound of formula (I), wherein W, X, Y, and Z have the meaning indicated in the description while CDC represents one of the dicarbonyl radicals mentioned in the description, and (b) at least one compound that improves crop plant tolerance and is part of the group of compounds indicated in the description. Also disclosed is a method for controlling insects and/or arachnids using the inventive agents.

Description

Selective insecticides and/or acaricides based on substituted cyclic dicarbonyl compounds and safeners

The present invention relates to the use of selective insecticidal and/or acaricidal active compound combinations (combinations) comprising, firstly, a substituted cyclic dicarbonyl compound and, secondly, at least one crop compatibility-improving compound, which combinations are useful for the selective control of insects and/or spider mites in various crops of useful plants.

4-chloro-and 4-nitro-4-phenyl-pyrazolyl-3, 5-dione (WO 99/20610) is known to have herbicidal action, and 3-halo-and 3-nitro-3-phenyl-substituted pyrrolidine-2, 4-dione and 4-oxofuran-2-one (JP-A12086628) has acaricidal and insecticidal action, and their herbicidal, acaricidal and insecticidal action is also known from WO 03/029213, DE-A10301805, WO 03/045957 and WO 2004/069841.

2-chloro-2-phenylcyclopentane-1, 3-dione and 2-chloro-2-phenylcyclohexane-1, 3-dione are also known from WO 2004/037749.

4-chloro-4-phenylpyrazolidine-3, 5-dione having herbicidal and insecticidal/acaricidal action is likewise known from WO 2005/016933.

Furthermore, selective herbicides based on substituted cyclic dicarbonyl compounds and safeners have also been described (WO 2004/064520).

However, the compatibility of these compounds, in particular with monocotyledonous crops, is not entirely satisfactory in all cases.

Surprisingly, it has now been found that certain substituted cyclic dicarbonyl compounds, when used together with the below described compounds improving crop compatibility (safeners/antidotes), provide excellent protection against crop damage and can be used particularly advantageously as a combination preparation with a broad spectrum of action for the selective control of insects, even in crops of beneficial monocotyledonous plants, such as in cereals.

The present invention provides the use of selective insecticidal and/or acaricidal compositions comprising an effective amount of active compound combinations for controlling insects and/or arachnids, which active compound combinations comprise the following components:

(a) at least one substituted cyclic dicarbonyl compound of formula (I) including all isomeric forms

Wherein,

w and Z independently of one another represent hydrogen, halogen, alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, haloalkyl, haloalkoxy, haloalkenyloxy, nitro or cyano,

x represents halogen, alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkyl, haloalkoxy, haloalkenyloxy, nitro or cyano,

y represents hydrogen, halogen, alkyl, haloalkyl, haloalkoxy, nitro, cyano or represents optionally substituted phenyl or heteroaryl,

CDC represents one of the following groups

Or

Wherein,

a represents hydrogen, in each case optionally halogenated alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, saturated or unsaturated optionally substituted cycloalkyl in which optionally at least one ring atom is replaced by a heteroatom, or aryl, aralkyl or heteroaryl in each case optionally substituted by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, cyano or nitro,

b represents hydrogen, alkyl or alkoxyalkyl, or

A and B together with the carbon atom to which they are attached represent a saturated or unsaturated, unsubstituted or substituted ring optionally containing at least one heteroatom,

d represents hydrogen or an optionally substituted group selected from: alkyl, alkenyl, alkynyl, alkoxyalkyl, saturated or unsaturated cycloalkyl in which optionally one or more ring atoms are replaced by heteroatoms, aralkyl, aryl, heteroarylalkyl or heteroaryl, or

A and D, together with the atoms to which they are each attached, represent a saturated or unsaturated ring, partially unsubstituted or substituted A, D and optionally containing at least one heteroatom, or

A and Q¹Together represent alkanediyl or alkenediyl which are optionally substituted by hydroxy or by alkyl, alkoxy, alkylthio, cycloalkyl, benzyloxy or aryl, each of which is optionally substituted, or

Q¹Represents hydrogen or an alkyl group,

Q²、Q⁴、Q⁵and Q⁶Independently of one another, represents hydrogen or an alkyl radical,

Q³represents hydrogen, alkyl, alkoxyalkyl, alkylthioalkyl, optionally substituted cycloalkyl in which optionally one methylene group is replaced by oxygen or sulfur, or optionally substituted phenyl, or

Q³And Q⁴Together with the carbon atom to which they are attached represent a saturated or unsaturated, substituted or unsubstituted ring optionally containing one heteroatom,

g represents halogen or nitro;

and

(b) at least one crop compatibility-improving compound selected from the group consisting of:

4-Dichloroacetyl-1-oxa-4-azaspiro [4.5] decane (AD-67, MON-4660), 1-Dichloroacetyl-hexahydro-3, 3, 8 a-trimethylpyrrolo [1, 2-a ] pyrimidin-6 (2H) -one (dicyclonon, BAS-145138),

4-dichloroacetyl-3, 4-dihydro-3-methyl-2H-1, 4-benzoxazine (benoxacor)),

1-methylhexyl 5-chloroquinoline-8-oxoacetate (cloquintocet-mexyl), cf. EP-A-86750, EP-A-94349, EP-A-191736, related compounds from EP-A-492366),

3- (2-chlorophenylmethyl) -1- (1-methyl-1-phenylethyl) urea (cumyluron (R)),

alpha- (cyano methoxyimino) phenylacetonitrile (metameril),

2, 4-dichlorophenoxyacetic acid (2, 4-D),

4- (2, 4-dichlorophenoxy) butanoic acid (2, 4-DB),

1- (1-methyl-1-phenylethyl) -3- (4-methylphenyl) urea (dazomet, dymron)),

3, 6-dichloro-2-methoxybenzoic acid (dicamba),

Piperidine-1-carbothioic acid-S-1-methyl-1-phenylethyl ester (dimeperate),

2, 2-dichloro-N- (2-oxo-2- (2-propenylamino) ethyl) -N- (2-propenyl) acetamide (DKA-24),

2, 2-dichloro-N, N-di-2-propenylacetamide (dichlormid),

4, 6-dichloro-2-phenylpyrimidine (fenclorim)),

ethyl 1- (2, 4-dichlorophenyl) -5-trichloromethyl-1H-1, 2, 4-triazole-3-carboxylate (fenchlorazole-ethyl, see EP-A-174562 and EP-A-346620 for reference),

2-chloro-4-trifluoromethylthiazole-5-carboxylic acid phenylmethyl ester (fluzazole),

4-chloro-N- (1, 3-dioxolan-2-yl-methoxy) -alpha-trifluoroacetyl ketoxime (fluxofenim),

3-dichloroacetyl-5- (2-furyl) -2, 2-dimethyloxazolidine (furilazole), MON-13900),

Ethyl 4, 5-dihydro-5, 5-diphenyl-3-isoxazolecarboxylate (isoxadifen-ethyl, see WO-A-95/07897 for related compounds),

1- (ethoxycarbonyl) ethyl 3, 6-dichloro-2-methoxybenzoate (lactidichlor),

(4-chloro-o-tolyloxy) acetic acid (MCPA),

2- (4-chloro-o-tolyloxy) propionic acid (2-methyl-4-chloropropionic acid (mecoprop)),

diethyl 1- (2, 4-dichlorophenyl) -4, 5-dihydro-5-methyl-1H-pyrazole-3, 5-dicarboxylate (mefenpyr-diethyl, see WO-A-91/07874 for related compounds),

2-dichloromethyl-2-methyl-1, 3-dioxolane (MG-191),

2-propenyl-1-oxa-4-azaspiro [4.5] decane-4-dithiocarboxylic ester (MG-838),

1, 8-naphthalic anhydride,

Alpha- (1, 3-dioxolan-2-yl-methoxyimino) phenylacetonitrile (oxabetrinil),

2, 2-dichloro-N- (1, 3-dioxolan-2-yl-methyl) -N- (2-propenyl) acetamide (PPG-1292),

3-dichloroacetyl-2, 2-dimethyloxazolidine (R-28725),

3-dichloroacetyl-2, 2, 5-trimethyloxazolidine (R-29148),

4- (4-chloro-o-tolyl) butanoic acid,

4- (4-chlorophenoxy) butyric acid,

Diphenyl methoxyacetic acid,

Methyl diphenylmethoxyacetate,

Ethyl diphenylmethoxyacetate,

1- (2-chlorophenyl) -5-phenyl-1H-pyrazole-3-carboxylic acid methyl ester,

1- (2, 4-dichlorophenyl) -5-methyl-1H-pyrazole-3-carboxylic acid ethyl ester,

1- (2, 4-dichlorophenyl) -5-isopropyl-1H-pyrazole-3-carboxylic acid ethyl ester,

1- (2, 4-dichlorophenyl) -5- (1, 1-dimethylethyl) -1H-pyrazole-3-carboxylic acid ethyl ester,

1- (2, 4-dichlorophenyl) -5-phenyl-1H-pyrazole-3-carboxylic acid ethyl ester (cf. related compounds of EP-A-269806 and EP-A-333131),

5- (2, 4-dichlorobenzyl) -2-isoxazoline-3-carboxylic acid ethyl ester,

5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester,

Ethyl 5- (4-fluorophenyl) -5-phenyl-2-isoxazoline-3-carboxylate (see related compounds in WO-A-91/08202),

5-chloroquinoline-8-oxyacetic acid-1, 3-dimethylbut-1-yl ester,

5-chloroquinoline-8-oxyacetic acid-4-allyloxybutyl ester,

5-chloroquinoline-8-oxyacetic acid-1-allyloxypropan-2-yl ester,

5-chloroquinoxaline-8-oxoacetic acid methyl ester,

5-chloroquinoline-8-oxyacetic acid ethyl ester,

5-chloroquinoxaline-8-oxyacetic acid allyl ester,

5-chloroquinoline-8-oxyacetic acid-2-oxoprop-1-yl ester,

5-chloroquinoline-8-oxomalonic acid diethyl ester,

5-chloroquinoxaline-8-yloxymalonic acid diallyl ester,

Diethyl 5-chloroquinoline-8-oxomalonate (cf. related compounds in EP-A-582198),

4-carboxychroman-4-ylacetic acids (AC-304415, cf. EP-A-613618),

4-chlorophenoxyacetic acid,

3, 3' -dimethyl-4-methoxy benzophenone,

1-bromo-4-chloromethylsulfonyl benzene,

1- [4- (N-2-methoxybenzoylsulfamoyl) phenyl ] -3-methylurea (i.e. N- (2-methoxybenzoyl) -4- [ (methylaminocarbonyl) amino ] benzenesulfonamide),

1- [4- (N-2-methoxybenzoylsulfamoyl) phenyl ] -3, 3-dimethylurea,

1- [4- (N-4, 5-dimethylbenzoylsulfamoyl) phenyl ] -3-methylurea,

1- [4- (N-naphthylsulfamoyl) phenyl ] -3, 3-dimethylurea,

N- (2-methoxy-5-methylbenzoyl) -4- (cyclopropylaminocarbonyl) benzenesulfonamide,

and/or one of the following compounds defined by the general formula,

general formula (IIa)

Or general formula (IIb)

Or of the general formula (IIc)

Wherein

m represents the number 0, 1, 2, 3, 4 or 5,

A¹represents one of the divalent heterocyclic groups shown below

n represents the number 0, 1, 2, 3, 4 or 5,

A²represents optionally substituted by C₁-C₄Alkyl and/or C₁-C₄Alkoxycarbonyl and/or C₁-C₄Alkenyloxycarbonyl-substituted alkanediyl having 1 or 2 carbon atoms,

R⁸represents hydroxy, mercapto, amino, C₁-C₆Alkoxy radical, C₁-C₆Alkylthio radical, C₁-C₆Alkylamino or di- (C)₁-C₄Alkyl) amino group(s),

R⁹represents hydroxy, mercapto, amino, C₁-C₇Alkoxy radical, C₁-C₆Alkenyloxy radical, C₁-C₆alkenyloxy-C₁-C₆Alkoxy radical, C₁-C₆Alkylthio radical, C₁-C₆Alkylamino or di- (C)₁-C₄Alkyl) amino group(s),

R¹⁰represents C, each of which is optionally substituted by fluorine, chlorine and/or bromine₁-C₄An alkyl group, a carboxyl group,

R¹¹represents hydrogen or represents C, each of which is optionally substituted by fluorine, chlorine and/or bromine₁-C₆Alkyl radical, C₂-C₆Alkenyl or C₂-C₆Alkynyl, C₁-C₄alkoxy-C₁-C₄Alkyl, dioxolanyl-C₁-C₄Alkyl, furyl-C₁-C₄Alkyl, thienyl, thiazolyl, piperidinyl, or represents optionally fluoro, chloro and/or bromo or C₁-C₄A phenyl group substituted with an alkyl group,

R¹²represents hydrogen or represents C, each of which is optionally substituted by fluorine, chlorine and/or bromine₁-C₆Alkyl radical, C₂-C₆Alkenyl or C₂-C₆Alkynyl, C₁-C₄alkoxy-C₁-C₄Alkyl, dioxolanyl-C₁-C₄Alkyl, furyl-C₁-C₄Alkyl, thienyl, thiazolyl, piperidinyl, or represents optionally fluoro, chloro and/or bromo or C₁-C₄Alkyl-substituted phenyl, or

R¹¹And R¹²Together represent each optionally substituted by C₁-C₄Alkyl, phenyl, furyl, fused benzene rings, or C substituted by two substituents₃-C₆Alkanediyl or C₂-C₅Oxaalkanediyl, said two substituents forming together with the C atom to which they are attached a 5-or 6-membered carbocyclic ring,

R¹³represents hydrogen, cyano, halogen or represents C, each of which is optionally substituted by fluorine, chlorine and/or bromine₁-C₄Alkyl radical, C₃-C₆A cycloalkyl group or a phenyl group, or a substituted or unsubstituted cycloalkyl group,

R¹⁴represents hydrogen or optionally substituted by hydroxy, cyano, halogen or C₁-C₄Alkoxy-substituted C₁-C₆Alkyl radical, C₃-C₆Cycloalkyl or tri- (C)₁-C₄An alkyl) silyl group, a silyl group,

R¹⁵represents hydrogen, cyano, halogen or represents C, each of which is optionally substituted by fluorine, chlorine and/or bromine₁-C₄Alkyl radical, C₃-C₆A cycloalkyl group or a phenyl group, or a substituted or unsubstituted cycloalkyl group,

X¹represents nitro, cyano, halogen, C₁-C₄Alkyl radical, C₁-C₄Haloalkyl, C₁-C₄Alkoxy or C₁-C₄A halogenated alkoxy group,

X²represents hydrogen, cyano, nitro, halogen, C₁-C₄Alkyl radical, C₁-C₄Haloalkyl, C₁-C₄Alkoxy or C₁-C₄A halogenated alkoxy group,

X³represents hydrogen, cyano, nitro, halogen, C₁-C₄Alkyl radical, C₁-C₄Haloalkyl, C₁-C₄Alkoxy or C₁-C₄A halogenated alkoxy group,

and/or the following compounds defined by the general formula,

general formula (IId)

Or of the general formula (IIe)

Wherein

t represents the number 0, 1, 2, 3, 4 or 5,

v represents the number 0, 1, 2, 3, 4 or 5,

R¹⁶represents hydrogen or C₁-C₄An alkyl group, a carboxyl group,

R¹⁷represents hydrogen or C₁-C₄An alkyl group, a carboxyl group,

R¹⁸represents hydrogen or represents in each case optionally cyano-, halogen or C₁-C₄Alkoxy-substituted C₁-C₆Alkyl radical, C₁-C₆Alkoxy radical, C₁-C₆Alkylthio radical, C₁-C₆Alkylamino or di- (C)₁-C₄Alkyl) amino, or represents in each case optionally cyano, halogen or C₁-C₄Alkyl substituted C₃-C₆Cycloalkyl radical, C₃-C₆Cycloalkyl oxy, C₃-C₆Cycloalkylthio radicals or C₃-C₆A cycloalkylamino group,

R¹⁹represents hydrogen or optionally cyano, hydroxy, halogen or C₁-C₄Alkoxy-substituted C₁-C₆Alkyl or represents C, each of which is optionally substituted by cyano or halogen₃-C₆Alkenyl or C₃-C₆Alkynyl or represents optionally cyano, halogen or C₁-C₄Alkyl substituted C₃-C₆A cycloalkyl group,

R²⁰represents hydrogen or optionally cyano, hydroxy, halogen or C₁-C₄Alkoxy-substituted C₁-C₆Alkyl or represents C, each of which is optionally substituted by cyano or halogen₃-C₆Alkenyl or C₃-C₆Alkynyl or represents optionally cyano, halogen or C₁-C₄Alkyl substituted C₃-C₆Cycloalkyl or represents optionally nitro, cyano, halogen, C₁-C₄Alkyl radical, C₁-C₄Haloalkyl, C₁-C₄Alkoxy or C₁-C₄Phenyl substituted by haloalkoxy, or with R¹⁹Together represent each optionally substituted by C₁-C₄Alkyl substituted C₂-C₆Alkanediyl or C₂-C₅An oxaalkanediyl group, which is an oxygen-containing heterocycle,

X⁴represents nitro, cyano, carboxyl, carbamoyl, formyl, aminosulfonyl, hydroxyl, amino, halogen, C₁-C₄Alkyl radical, C₁-C₄Haloalkyl, C₁-C₄Alkoxy or C₁-C₄A haloalkoxy group, and

X⁵represents nitro, cyano, carboxyl, carbamoyl, formyl, aminosulfonyl, hydroxyl, amino, halogen, C₁-C₄Alkyl radical, C₁-C₄Haloalkyl, C₁-C₄Alkoxy or C₁-C₄A haloalkoxy group.

In the above definitions, the hydrocarbon chain, such as alkyl or alkanediyl, including combinations with heteroatoms, such as alkoxy, may each be straight-chain or branched, respectively.

Among its various properties, the compounds of the formula (I) may, depending mainly on the nature of the substituents, be present as geometric and/or optical isomers or as mixtures of isomers of different composition, which mixtures may, if appropriate, be separated in a customary manner. The present invention provides pure isomers and isomer mixtures, their use and compositions containing them. For the sake of simplicity, however, the compounds of the formula (I) are referred to in each case only, but with the meaning of pure compounds and, if appropriate, also mixtures of isomers in different proportions.

In view of the meanings (1) to (6) of the CDC group, the following basic structures (I-1) to (I-6) result:

wherein,

A、B、D、G、Q¹、Q²、Q³、Q⁴、Q⁵、Q⁶w, X, Y and Z are as defined above.

Formula (I) provides a broad definition of substituted cyclic dicarbonyl compounds for insecticidal and/or acaricidal compositions. Preferred substituent or group ranges in the formulae set forth above and below are set forth below:

w and Z independently of one another preferably represent hydrogen, halogen, C₁-C₆Alkyl radical, C₁-C₆Haloalkyl or C₁-C₆An alkoxy group,

x preferably represents halogen, C₁-C₆Alkyl radical, C₂-C₆Alkenyl radical, C₂-C₆Alkynyl, C₁-C₆Haloalkyl, C₁-C₆Alkoxy radical, C₃-C₆Alkenyloxy radical, C₁-C₆Haloalkoxy, C₃-C₆Haloalkenyloxy, nitro or cyano,

y preferably represents hydrogen, halogen, C₁-C₄Alkyl radical, C₁-C₂Haloalkyl, C₁-C₂Haloalkoxy, cyano or one of the following

Wherein,

V¹preferably represents hydrogen, halogen, C₁-C₁₂Alkyl radical, C₁-C₆Alkoxy radical, C₁-C₄Haloalkyl, C₁-C₄Haloalkoxy, nitro or cyano, or a pharmaceutically acceptable salt thereof,

V²and V³Independently of one another preferably represents hydrogen, halogen, C₁-C₆Alkyl radical, C₁-C₆Alkoxy radical, C₁-C₄Haloalkyl or C₁-C₄A halogenated alkoxy group,

CDC preferably represents one of the following groups

A preferably represents hydrogen or in each case optionally halogenated C₁-C₁₂Alkyl radical, C₃-C₈Alkenyl radical, C₁-C₁₀alkoxy-C₁-C₈Alkyl radical, C₁-C₁₀alkylthio-C₁-C₆Alkyl, optionally substituted by halogen, C₁-C₆Alkyl or C₁-C₆Alkoxy-substituted C in which optionally one or two not directly adjacent ring atoms are replaced by oxygen and/or sulfur₃-C₈Cycloalkyl or represents each optionally halogen, C₁-C₆Alkyl radical, C₁-C₆Haloalkyl, C₁-C₆Alkoxy radical, C₁-C₆Phenyl or phenyl-C substituted by haloalkoxy, cyano or nitro₁-C₆An alkyl group, a carboxyl group,

b preferably represents hydrogen, C₁-C₁₂Alkyl or C₁-C₈alkoxy-C₁-C₆Alkyl, or

A. B together with the carbon atom to which they are attached preferably represents wherein optionally one ring atom is replaced by oxygen or sulphur and optionally by C₁-C₈Alkyl radical, C₃-C₁₀Cycloalkyl radical, C₁-C₈Haloalkyl, C₁-C₈Alkoxy radical, C₁-C₈Alkylthio, halogen or phenyl mono-or disubstituted saturated C₃-C₁₀Cycloalkyl or unsaturated C₅-C₁₀Cycloalkyl radicals, or

A. B together with the carbon atom to which they are attached preferably represents C substituted by alkylenediyl, alkylenedioxy or alkylenedisulfide₅-C₆Cycloalkyl, said alkylenediyl being optionally substituted by C₁-C₄Alkyl substituted and optionally containing one or two indirect phasesOrtho-oxygen and/or sulfur atoms, said alkylenedioxy or alkylenedisulfide group together with the carbon atom to which it is attached forming another five to eight membered ring, or

A. B together with the carbon atom to which they are attached preferably represents C₃-C₈Cycloalkyl or C₅-C₈Cycloalkenyl in which two substituents each, together with the carbon atom to which they are attached, represent each optionally substituted by C₁-C₆Alkyl radical, C₁-C₆Alkoxy-or halogen-substituted C in which optionally one methylene group is replaced by oxygen or sulphur₂-C₆Alkanediyl, C₂-C₆Alkenediyl or C₄-C₆(ii) an alkanedienediyl group,

d preferably represents hydrogen, represents in each case optionally halogenated C₁-C₁₂Alkyl radical, C₃-C₈Alkenyl radical, C₃-C₈Alkynyl, C₁-C₁₀alkoxy-C₂-C₈Alkyl, optionally substituted by halogen, C₁-C₄Alkyl radical, C₁-C₄Alkoxy or C₁-C₄Haloalkyl-substituted C in which optionally one ring atom is replaced by oxygen or sulphur₃-C₈Cycloalkyl, or each optionally substituted by halogen, C₁-C₆Alkyl radical, C₁-C₆Haloalkyl, C₁-C₆Alkoxy radical, C₁-C₆Phenyl or phenyl-C substituted by haloalkoxy, cyano or nitro₁-C₆An alkyl group, a carboxyl group,

a and D together preferably represent in each case optionally substituted C₃-C₆Alkanediyl or C₃-C₆Alkenediyl, in which optionally one methylene group is replaced by a carbonyl group, oxygen or sulphur,

suitable substituents are each:

halogen, hydroxy, mercapto or in each case optionally halogenated C₁-C₁₀Alkyl or C₁-C₆Alkoxy, or another C₃-C₆Alkanediyl, C₃-C₆An alkenediyl or butadienyl radical, the other C₃-C₆Alkanediyl, C₃-C₆Alkenediyl or butadienyl optionally substituted by C₁-C₆Alkyl substitution or in which optionally two adjacent substituents together with the carbon atom to which they are each attached form another saturated or unsaturated ring having 5 or 6 ring atoms which may contain oxygen or sulfur (in the case of compounds of formula (I-1), A and D together with the atoms to which they are attached preferably represent, for example, the following AD-1 to AD-10 groups),

a and Q¹Together preferably represent each optionally mono-or disubstituted by identical or different substituents from the following and are each optionally monosubstituted or disubstituted by C₁-C₂Alkanediyl or C bridged by an oxygen atom₃-C₆Alkanediyl or C₄-C₆Alkenediyl, which is selected from halogen, C, each of which is optionally mono-to trisubstituted by identical or different halogen₁-C₁₀Alkyl radical, C₁-C₆Alkoxy radical, C₁-C₆Alkylthio radical, C₃-C₇Cycloalkyl, and each optionally identical or different from halogen, C₁-C₆Alkyl and C₁-C₆A substituent of an alkoxy group is mono-to trisubstituted benzyloxy and phenyl, or

Q¹Preferably represents hydrogen or C₁-C₄An alkyl group, a carboxyl group,

Q²、Q⁴、Q⁵and Q⁶Independently of one another preferably represents hydrogen or C₁-C₄An alkyl group, a carboxyl group,

Q³preferably represents hydrogen, C₁-C₆Alkyl radical, C₁-C₆alkoxy-C₁-C₂Alkyl radical, C₁-C₆alkylthio-C₁-C₂Alkyl, optionally substituted by halogen, C₁-C₄Alkyl or C₁-C₄Alkoxy-substituted C in which optionally one methylene group is replaced by oxygen or sulphur₃-C₈Cycloalkyl or represents optionally halogen, C₁-C₄Alkyl radical, C₁-C₄Alkoxy radical, C₁-C₂Haloalkyl, C₁-C₂Phenyl substituted by haloalkoxy, cyano or nitro, or

Q³And Q⁴Together with the carbon atom to which they are attached preferably represent optionally substituted C₁-C₄Alkyl radical, C₁-C₄Alkoxy or C₁-C₂Haloalkyl-substituted C₃-C₇A ring in which optionally one ring atom is replaced by oxygen or sulphur,

g preferably represents chlorine, bromine or nitro.

In the radical definitions mentioned as preferred, halogen stands for fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine.

W and Z independently of one another particularly preferably represent hydrogen, chlorine, bromine, C₁-C₃Alkyl or C₁-C₃An alkoxy group,

x particularly preferably represents chlorine, bromine, C₁-C₄Alkyl radical, C₁-C₄Alkoxy radical, C₁-C₃Haloalkyl, C₁-C₃A haloalkoxy group or a cyano group,

y particularly preferably represents hydrogen, chlorine, bromine, C₁-C₂Alkyl, trifluoromethyl or represent the following groups

V¹Particularly preferably represents hydrogen, fluorine, chlorine, bromine, C₁-C₆Alkyl radical, C₁-C₄Alkoxy radical, C₁-C₂Haloalkyl, C₁-C₂Haloalkoxy, nitro or cyano, or a pharmaceutically acceptable salt thereof,

V²particularly preferably represents hydrogen, fluorine, chlorineBromine, C₁-C₄Alkyl radical, C₁-C₄Alkoxy radical, C₁-C₂Haloalkyl or C₁-C₂A halogenated alkoxy group,

CDC particularly preferably represents one of the following groups

A particularly preferably represents hydrogen, represents C which is in each case optionally mono-to trisubstituted by fluorine or chlorine₁-C₆Alkyl radical, C₁-C₄alkoxy-C₁-C₂Alkyl or represents optionally fluorine, chlorine, C₁-C₂Alkyl or C₁-C₂Alkoxy mono-or disubstituted C₃-C₇A cycloalkyl group,

b particularly preferably represents hydrogen or C₁-C₆Alkyl, or

A. B together with the carbon atom to which they are attached particularly preferably represents wherein optionally one ring atom is replaced by oxygen or sulphur and optionally by C₁-C₄Alkyl radical, C₁-C₂Haloalkyl or C₁-C₄Alkoxy monosubstituted saturated C₃-C₇Cycloalkyl with the proviso that Q³Particularly preferably represents hydrogen or methyl, or

A. B together with the carbon atom to which they are attached particularly preferably represents C substituted by alkylenediyl or alkylenedioxy₅-C₆Cycloalkyl, said alkylenedioxy optionally containing one or two oxygen or sulfur atoms which are not directly adjacent and optionally being substituted by methyl or ethyl, said alkylenedioxy group and being attached theretoThe carbon atoms to be bonded together form another five-or six-membered ring, with the proviso that Q³Particularly preferably represents hydrogen or methyl, or

A. B together with the carbon atom to which they are attached particularly preferably represents C₃-C₆Cycloalkyl or C₅-C₆Cycloalkenyl in which two substituents, together with the carbon atom to which they are each attached, represent C optionally one methylene group being replaced by oxygen₂-C₄Alkanediyl, C₂-C₄Alkenediyl, or represents butadienediyl, each of which is optionally mono-substituted by methyl or methoxy, with the proviso that Q³Particularly preferably represents hydrogen or a methyl group,

d particularly preferably represents hydrogen, represents C which is in each case optionally mono-to trisubstituted by fluorine or chlorine₁-C₆Alkyl radical, C₃-C₆Alkenyl radical, C₁-C₄alkoxy-C₂-C₃Alkyl, represents optionally substituted C₁-C₂Alkyl radical, C₁-C₂C mono-substituted alkoxy or trifluoromethyl and wherein optionally one methylene group is replaced by oxygen or sulphur₃-C₇Cycloalkyl, or (but not of formula (I-1)) represents independently optionally fluoro, chloro, bromo, C₁-C₄Alkyl radical, C₁-C₂Haloalkyl, C₁-C₄Alkoxy or C₁-C₂A haloalkoxy mono-or disubstituted phenyl, pyridyl or benzyl group, or

A and D together particularly preferably represent optionally substituted C in which one methylene group is replaced by oxygen or sulphur₃-C₅Alkanediyl, possible substituents being C₁-C₂Alkyl, or

A and D (when a compound of formula (I-1)) together with the atom to which they are each attached particularly preferably represent one of the groups AD-1 to AD-10:

a and Q¹Together particularly preferably represent each optionally selected from C₁-C₂Alkyl and C₁-C₂C of alkoxy which is monosubstituted or disubstituted by identical or different substituents₃-C₄Alkanediyl or C₃-C₄An alkenediyl radical, or

Q¹It particularly preferably represents hydrogen,

Q²it particularly preferably represents hydrogen,

Q⁴、Q⁵and Q⁶Independently of one another, particularly preferably represents hydrogen or C₁-C₂An alkyl group, a carboxyl group,

Q³particularly preferably represents hydrogen, C₁-C₄Alkyl radical, C₁-C₄alkoxy-C₁-C₂Alkyl radical, C₁-C₄alkylthio-C₁-C₂Alkyl, or C optionally substituted by methyl or methoxy wherein optionally one methylene group is replaced by oxygen or sulphur₃-C₆Cycloalkyl radicals, or

Q³And Q⁴Together with the carbon atom to which they are attached particularly preferably represents optionally substituted C₁-C₄Alkyl or C₁-C₄Saturated C mono-or disubstituted by alkoxy and in which optionally one ring atom is replaced by oxygen or sulphur₅-C₆The shape of the ring is such that,

with the proviso that A particularly preferably represents hydrogen or methyl,

g particularly preferably represents chlorine or nitro.

In the radical definitions mentioned as being particularly preferred, halogen represents fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine.

W and Z independently of one another very particularly preferably represent hydrogen, chlorine, bromine, methyl, ethyl, methoxy or ethoxy,

x very particularly preferably represents chlorine, bromine, methyl, ethyl, propyl, methoxy, ethoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy or cyano,

y very particularly preferably represents hydrogen, chlorine, bromine, methyl, trifluoromethyl or represents the following group

V¹Very particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, tert-butyl, methoxy, trifluoromethyl or trifluoromethoxy,

V²very particularly preferably represents hydrogen, fluorine, chlorine, methyl, methoxy or trifluoromethyl,

very particular preference is given to CDC representing one of the following groups

A very particularly preferably represents hydrogen, represents C which is in each case optionally mono-to trisubstituted by fluorine₁-C₄Alkyl or C₁-C₂alkoxy-C₁-C₂Alkyl or represents C optionally mono-substituted by fluorine, methyl or methoxy₃-C₆A cycloalkyl group,

b very particularly preferably represents hydrogen, methyl or ethyl, or

A. B together with the carbon atom to which they are attached is very particularly preferredTable C saturated C wherein optionally one ring atom is replaced by oxygen and optionally monosubstituted by methyl, trifluoromethyl, methoxy, ethoxy, propoxy, butoxy or isobutoxy₅-C₆Cycloalkyl with the proviso that Q³Very particularly preferably represents hydrogen, or

A. B together with the carbon atom to which they are attached very particularly preferably represents C which is substituted by an alkylenedioxy group containing two oxygen atoms which are not directly adjacent₅-C₆Cycloalkyl with the proviso that Q³Very particularly preferably represents hydrogen,

d very particularly preferably represents hydrogen, represents C which is in each case optionally mono-to trisubstituted by fluorine₁-C₄Alkyl radical, C₃-C₄Alkenyl radical, C₁-C₂alkoxy-C₂-C₃Alkyl or C in which optionally one methylene group is replaced by oxygen or sulphur₃-C₆Cycloalkyl, or (but not for the compound of formula (I-1)) represents phenyl or pyridyl, each of which is optionally mono-or disubstituted by fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, trifluoromethyl or trifluoromethoxy, or

A and D together very particularly preferably represent optionally substituted C in which optionally one carbon atom is replaced by oxygen or sulphur and which is optionally mono-or disubstituted by methyl₃-C₅Alkanediyl, or

A and D (when a compound of formula (I-1)) together with the atoms to which they are each attached very particularly preferably represent a group:

a and Q¹Very particularly preferably together represent C which is optionally mono-or disubstituted by methyl or methoxy₃-C₄Alkanediyl, or

Q¹Very particularly preferred isThe compound is shown in the specification of hydrogen,

Q²very particularly preferably represents hydrogen,

Q⁴、Q⁵and Q⁶Very particularly preferably represents, independently of one another, hydrogen or methyl,

Q³very particularly preferably represents hydrogen, methyl, ethyl or C₃-C₆Cycloalkyl radicals, or

Q³And Q⁴Very particularly preferably, together with the carbon atom to which they are attached, represents saturated C which is optionally mono-substituted by methyl or methoxy and in which optionally one ring atom is replaced by oxygen or sulphur₅-C₆Ring, with the proviso that A very particularly preferably represents hydrogen,

g very particularly preferably represents chlorine or nitro,

w particularly preferably represents hydrogen, chlorine, bromine, methyl, ethyl, methoxy or ethoxy,

x particularly preferably represents chlorine, bromine, methyl, ethyl, propyl, methoxy, ethoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy or cyano,

y particularly preferably represents hydrogen, chlorine, bromine, methyl, trifluoromethyl or represents the following group

V¹Particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, tert-butyl, methoxy, trifluoromethyl or trifluoromethoxy,

V²particularly preferably represents hydrogen, fluorine, chlorine, methyl, methoxy or trifluoromethyl,

z particularly preferably represents hydrogen, methyl, chlorine or bromine,

CDC particularly preferably represents one of the following groups

A particularly preferably represents hydrogen, represents C which is in each case optionally mono-to trisubstituted by fluorine₁-C₄Alkyl or C₁-C₂alkoxy-C₁-C₂Alkyl or represents C optionally mono-substituted by fluorine, methyl or methoxy₃-C₆A cycloalkyl group,

b particularly preferably represents hydrogen, methyl or ethyl, or

A. B together with the carbon atom to which they are attached particularly preferably represents saturated C in which optionally one ring atom is replaced by oxygen and optionally monosubstituted by methyl, trifluoromethyl, methoxy, ethoxy, propoxy, butoxy or isobutoxy₅-C₆A cycloalkyl group,

d particularly preferably represents hydrogen,

g particularly preferably represents chlorine.

The broad or preferred radical definitions or specifications mentioned above may be combined with one another as desired, i.e. including combinations between ranges and preferred ranges.

The present invention preferably uses compounds of the formula (I) which comprise a combination of the preferred (preferred) meanings mentioned above.

Particular preference is given according to the invention to the use of compounds of the formula (I) which comprise a combination of the meanings mentioned as being particularly preferred.

Very particular preference is given according to the invention to the use of compounds of the formula (I) which comprise a combination of the meanings mentioned above as being very particularly preferred.

The present invention particularly preferably uses compounds of the formula (I) which comprise a combination of the abovementioned particularly preferred meanings.

Saturated or unsaturated hydrocarbon radicals, such as alkyl, alkylenediyl or alkenyl radicals, including combinations with heteroatoms, such as alkoxy radicals, can, to the extent possible, each be linear or branched, respectively.

Unless otherwise indicated, an optionally substituted group may be mono-or polysubstituted, wherein in the case of polysubstitution the substituents may be the same or different.

In addition to the compounds set forth in the examples, the following compounds of formula (I-1) may be specifically set forth:

table 1:W＝CH₃，X＝CH₃，Y＝4-CH₃，Z＝H

table 2:A. b and D are as described in Table 1

W＝CH₃；X＝CH₃；Y＝4-Cl；Z＝H；

Table 3:A. b and D are as described in Table 1

W＝CH₃；X＝CH₃；Y＝4-Br；Z＝H；

Table 4:A. b and D are as described in Table 1

W＝C₂H₅；X＝CH₃；Y＝4-Cl；Z＝H；

Table 5:A. b and D are as described in Table 1

W＝C₂H₅；X＝CH₃；Y＝4-Br；Z＝H；

Table 6:A. b and D are as described in Table 1

W＝C₂H₅；X＝C₂H₅；Y＝4-Cl；Z＝H；

Table 7:A. b and D are as described in Table 1

W＝C₂H₅；X＝C₂H₅；Y＝4-Br；Z＝H；

Table 8:A. b and D are as described in Table 1

W＝CH₃；X＝Cl；Y＝4-Cl；Z＝H；

Table 9:A. b and D are as described in Table 1

W＝CH₃；X＝Br；Y＝4-Br；Z＝H；

Table 10:A. b and D are as described in Table 1

W＝CH₃；X＝Cl；Y＝4-Br；Z＝H；

Table 11:A. b and D are as described in Table 1

W＝CH₃；X＝Br；Y＝4-Cl；Z＝H；

Table 12:A. b and D are as described in Table 1

W＝C₂H₅；X＝Cl；Y＝4-Cl；Z＝H；

Table 13:A. b and D are as described in Table 1

W＝C₂H₅；X＝Br；Y＝4-Br；Z＝H；

Table 14:A. b and D are as described in Table 1

W＝C₂H₅；X＝Cl；Y＝4-Br；Z＝H；

Table 15:A. b and D are as described in Table 1

W＝C₂H₅；X＝Br；Y＝4-Cl；Z＝H；

Table 16:A. b and D are as described in Table 1

W＝H；X＝CH₃；Y＝H；Z＝H；

Table 17:A. b and D are as described in Table 1

W＝H；X＝Cl；Y＝H；Z＝H；

Table 18:A. b and D are as described in Table 1

W＝H；X＝Br；Y＝H；Z＝H；

Table 19:A. b and D are as described in Table 1

W＝H；X＝CH₃；Y＝4-Cl；Z＝H；

Table 20:A. b and D are as described in Table 1

W＝H；X＝Cl；Y＝4-CH₃；Z＝H；

Table 21:A. b and D are as described in Table 1

W＝H；X＝CH₃；Y＝4-CH₃；Z＝H；

Table 22:A. b and D are as described in Table 1

W＝H；X＝Cl；Y＝4-Cl；Z＝H；

Table 23:A. b and D are as described in Table 1

W＝H；X＝Cl；Y＝4-Br；Z＝H；

Table 24:A. b and D are as described in Table 1

W＝CH₃；X＝Cl；Y＝4-CH₃；Z＝H；

Table 25:A. b and D are as described in Table 1

W＝CH₃；X＝Br；Y＝4-CH₃；Z＝H；

Table 26:A. b and D are as described in Table 1

W＝C₂H₅；X＝Cl；Y＝4-CH₃；Z＝H；

Table 27:A. b and D are as described in Table 1

W＝C₂H₅；X＝Br；Y＝4-CH₃；Z＝H；

Table 28:A. b and D are as described in Table 1

W＝C₂H₅；X＝CH₃；Y＝4-CH₃；Z＝H；

Table 29:A. b and D are as described in Table 1

W＝C₂H₅；X＝C₂H₅；Y＝4-CH₃；Z＝H；

Table 30:A. b and D are as described in Table 1

W＝H；X＝CH₃；Y＝4-CH₃；Z＝5-CH₃.

Table 31:A. b and D are as described in Table 1

W＝H；X＝CH₃；Y＝4-Cl；Z＝5-CH₃.

Table 32:A. b and D are as described in Table 1

W＝H；X＝Br；Y＝4-CH₃；Z＝5-CH₃.

Table 33:A. b and D are as described in Table 1

W＝H；X＝Cl；Y＝4-Cl；Z＝5-CH₃.

Table 34:A. b and D are as described in Table 1

W＝H；X＝CH₃；Y＝4-Br；Z＝5-CH₃.

Table 35:A. b and D are as described in Table 1

W＝H；X＝Cl；Y＝4-CH₃；Z＝5-Cl.

Table 36:A. b and D are as described in Table 1

W＝H；X＝CH₃；Y＝H；Z＝5-CH₃.

Table 37:A. b and D are as described in Table 1

W＝H；X＝Cl；Y＝H；Z＝5-CH₃.

Table 38:A. b and D are as described in Table 1

W＝H；X＝Br；Y＝H；Z＝5-CH₃.

Table 39:A. b and D are as described in Table 1

W＝CH₃；X＝CH₃；Y＝4-CH₃；Z＝3-CH₃.

Table 40:A. b and D are as described in Table 1

W＝CH₃；X＝CH₃；Y＝4-CH₃；Z＝3-Cl，

Table 41:A. b and D are as described in Table 1

W＝CH₃；X＝CH₃；Y＝4-CH₃；Z＝3-Br.

Table 42:A. b and D are as described in Table 1

W＝CH₃；X＝CH₃；Y＝H；Z＝3-Cl.

Table 43:A. b and D are as described in Table 1

W＝CH₃；X＝CH₃；Y＝H；Z＝3-Br.

The compounds of the formula (I) are known essentially from the patent publications cited at the outset or they can be prepared by the processes described in said patent publications.

Preferred meanings of the abovementioned radicals in connection with the compounds of the formulae (IIa), (IIb), (IIc), (IId) and (IIe) ("herbicide safeners") which improve crop compatibility are defined below.

m preferably represents the number 0, 1, 2, 3 or 4.

A¹Preferably represents one of the divalent heterocyclic groups shown below

n preferably represents the number 0, 1, 2, 3 or 4.

A²Preferably represents methylene or ethylene, each of which is optionally substituted by methyl, ethyl, methoxycarbonyl, ethoxycarbonyl or allyloxycarbonyl.

R⁸Preferably represents hydroxyl, mercapto, amino, methoxy, ethoxy, n-or i-propoxy, n-butoxy, i-butoxy, s-or t-butoxy, methylthio, ethylthio, n-or i-propylthio, n-butylthio, i-butylthio, s-or t-butylthio, methylamino, ethylamino, n-or i-propylamino, n-butylamino, i-butylamino, s-or t-butylamino, dimethylamino or diethylamino.

R⁹Preferably represents hydroxyl, mercapto, amino, methoxy, ethoxy, n-or i-propoxy, n-butoxy, i-butoxy, sec-butoxyButoxy or tert-butoxy, 1-methylhexyloxy, allyloxy, 1-allyloxymethyl-ethoxy, methylthio, ethylthio, n-or isopropylthio, n-or tert-butylthio, isobutylthio, sec-or tert-butylthio, methylamino, ethylamino, n-or iso-propylamino, n-butylamino, isobutylamino, sec-or tert-butylamino, dimethylamino or diethylamino.

R¹⁰Preferably represents methyl, ethyl, n-propyl or isopropyl, each of which is optionally substituted by fluorine, chlorine and/or bromine.

R¹¹Preferably represents hydrogen, methyl, ethyl, n-or isopropyl, n-butyl, isobutyl, sec-or tert-butyl, propenyl, butenyl, propynyl or butynyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, dioxolanylmethyl, furyl, furylmethyl, thienyl, thiazolyl, piperidinyl, each of which is optionally substituted by fluorine, chlorine, methyl, ethyl, n-or isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl.

R¹²Preferably represents hydrogen, methyl, ethyl, n-or isopropyl, n-butyl, isobutyl, sec-or tert-butyl, propenyl, butenyl, propynyl or butynyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, dioxolanylmethyl, furyl, furylmethyl, thienyl, thiazolyl, piperidinyl, or phenyl, which is optionally substituted by fluorine, chlorine, methyl, ethyl, n-or isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, or with R, each of which is optionally substituted by fluorine and/or chlorine¹¹Together represent a group-CH optionally substituted by methyl, ethyl, furyl, phenyl, a fused benzene ring or by two substituents₂-O-CH₂-CH₂-and-CH₂-CH₂-O-CH₂-CH₂-one of said two substituents, together with the C atom to which they are attached, forming a 5 or 6 membered carbocyclic ring.

R¹³Preferably represents hydrogen, cyano, fluorine, chlorine, bromine or represents in each case optionally fluorine-, chlorine-and/or bromine-substituted methyl, ethyl, n-or isopropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or phenyl.

R¹⁴Preferably represents hydrogen, methyl, ethyl, n-or i-propyl, n-butyl, i-butyl, s-butyl or t-butyl, optionally substituted by hydroxyl, cyano, fluorine, chlorine, methoxy, ethoxy, n-or i-propoxy.

R¹⁵Preferably represents hydrogen, cyano, fluorine, chlorine, bromine or represents in each case optionally fluorine-, chlorine-and/or bromine-substituted methyl, ethyl, n-or isopropyl, n-butyl, isobutyl, sec-or tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or phenyl.

X¹Preferably represents nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n-or isopropyl, n-butyl, isobutyl, sec-or tert-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n-or isopropoxy, difluoromethoxy or trifluoromethoxy.

X²Preferably represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n-or isopropyl, n-butyl, isobutyl, sec-or tert-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n-or isopropoxy, difluoromethoxy or trifluoromethoxy.

X³Preferably represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n-or isopropyl, n-butyl, isobutyl, sec-or tert-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n-or isopropoxy, difluoromethoxy or trifluoromethoxy.

t preferably represents the number 0, 1, 2, 3 or 4.

v preferably represents the number 0, 1, 2, 3 or 4.

R¹⁶Preferably represents hydrogen, methyl, ethyl, n-propyl or isopropyl.

R¹⁷Preferably represents hydrogen, methyl, ethyl, n-propyl or isopropyl.

R¹⁸Preferably represents hydrogen, methyl, ethyl, n-propyl or isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, methoxy, ethoxy, n-propoxy or isopropoxy, n-butoxy, isobutoxy, sec-butoxy or tert-butoxy, methylthio, ethylthio, n-propylthio or isopropylthio, n-butylthio, isobutylthio, sec-butylthio or tert-butylthio, methylamino, ethylamino, n-propylamino or isopropylamino, n-butylamino, isobutylamino, sec-butylamino or tert-butylamino, dimethylamino or diethylamino, or cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, each of which is optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n-propyl or isopropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, n-propyloxy or isopropoxy, Cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino or cyclohexylamino.

R¹⁹Preferably represents hydrogen, methyl, ethyl, n-propyl or isopropyl, n-butyl, isobutyl or sec-butyl, in each case optionally substituted by cyano, hydroxyl, fluorine, chlorine, methoxy, ethoxy, n-propoxy or isopropoxy, propenyl, butenyl, propynyl or butynyl, in each case optionally substituted by cyano, fluorine, chlorine or bromine, or cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, in each case optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n-propyl or isopropyl.

R²⁰Preferably represents hydrogen, represents methyl, ethyl, n-propyl or isopropyl, n-butyl, isobutyl or sec-butyl, in each case optionally substituted by cyano, fluorine, chlorine or bromine, propenyl, butenyl, propynyl or butynyl, in each case optionally substituted by cyano, fluorine, chlorine or bromine, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, in each case optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n-propyl or isopropyl, or phenyl, in each case optionally substituted by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n-propyl or isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, trifluoromethyl, methoxy, ethoxy, n-propoxy or isopropoxy, difluoromethoxy or trifluoromethoxy, or is substituted with R¹⁹Together represent but-1, 4-diyl (1, 3-propylene), pent-1, 5-diyl, 1-oxabut-1, 4-diyl or 3-oxapent-1, 5-diyl, each of which is optionally substituted by methyl or ethyl.

X⁴Preferably represents nitro, cyano, carboxyl, carbamoyl, formyl, sulfamoyl, hydroxyl, amino, fluorine, chlorine, bromine, methyl, ethyl, n-or i-propyl, n-butyl, i-butyl, s-or t-butyl, trifluoromethyl, methoxy, ethoxy, n-or i-propoxy, difluoromethoxy or trifluoromethoxy.

X⁵Preferably represents nitro, cyano, carboxyl, carbamoyl, formyl, sulfamoyl, hydroxyl, amino, fluorine, chlorine, bromine, methyl, ethyl, n-or i-propyl, n-butyl, i-butyl, s-or t-butyl, trifluoromethyl, methoxy, ethoxy, n-or i-propoxy, difluoromethoxy or trifluoromethoxy.

Examples of compounds of the formula (IIa) which are very particularly preferred according to the invention as herbicide safeners are listed in the table below.

Table:examples of Compounds of formula (IIa)

Examples of compounds of the formula (IIb) which are very particularly preferred according to the invention as herbicide safeners are listed in the table below.

Watch (A)Examples of Compounds of formula (II b)

Examples of compounds of the formula (II c) which are very particularly preferred according to the invention as herbicide safeners are listed in the table below.

Table:examples of Compounds of formula (II c)

Examples of compounds of the formula (II d) which are very particularly preferred according to the invention as herbicide safeners are listed in the table below.

Watch (A)Examples of Compounds of formula (II d)

Examples of compounds of the formula (II e) which are very particularly preferred according to the invention as herbicide safeners are listed in the table below.

Watch (A)Examples of Compounds of formula (II e)

Most preferred as compounds for improving crop compatibility [ component (b) ] are: cloquintocet-mexyl, fenchlorazole, isoxadifen, mefenpyr-diethyl, fenclorim, cumarone, dichlormid, penflufen and compounds II e-5 and II e-11, with particular emphasis on cloquintocet-mexyl, mefenpyr-diethyl, isoxadifen, mefenpyr-diethyl, dichlormid, fenclorim and compound IIe-5.

Examples of selective herbicidal combinations according to the invention which each comprise an active compound of the formula (I) and one of the abovementioned safeners are listed in the table below.

Watch (A)Examples of conjugates of the invention

Active compounds of the formula (I)	Safeners
		I-1	Cloquintocet-mexyl
I-1	Fenchlorazole
		I-1	Biphenyl oxazole acid
I-1	Pyrazolyl cloquintocet-mexyl
		I-1	Grass-decomposing oxazole
I-1	Grass decompositionPyridine (I)
		I-1	Benzyweed-lon
I-1	Vanilla-Royle
		I-1	Allicamide
I-1	Picaodan
		I-1	IIe-11
I-1	IIe-5
		I-2	Cloquintocet-mexyl
I-2	Fenchlorazole
		I-2	Biphenyl oxazole acid
I-2	Pyrazolyl cloquintocet-mexyl
		I-2	Grass-decomposing oxazole
I-2	Fenclorim
		I-2	Benzyweed-lon
I-2	Vanilla-Royle
		I-2	Allicamide
I-2	Picaodan
		I-2	IIe-11

Active compounds of the formula (I)	Safeners
		I-2	II e-5
I-3	Cloquintocet-mexyl
		I-3	Fenchlorazole
I-3	Biphenyl oxazole acid
		I-3	Pyrazolyl cloquintocet-mexyl
I-3	Grass-decomposing oxazole
		I-3	Fenclorim
I-3	Benzyweed-lon
		I-3	Vanilla-Royle
I-3	Allicamide
		I-3	Picaodan
I-3	IIe-5
		I-3	IIe-11
I-4	Cloquintocet-mexyl
		I-4	Fenchlorazole
I-4	Biphenyl oxazole acid
		I-4	Pyrazolyl cloquintocet-mexyl
I-4	Grass-decomposing oxazole
		I-4	Fenclorim
I-4	Benzyweed-lon
		I-4	Vanilla-Royle
I-4	Allicamide
		I-4	Picaodan
I-4	II e-11
		I-4	II e-5
I-5	Cloquintocet-mexyl
		I-5	Fenchlorazole
I-5	Biphenyl oxazole acid
		I-5	Pyrazolyl cloquintocet-mexyl
I-5	Grass-decomposing oxazole

Active compounds of the formula (I)	Safeners
		I-5	Fenclorim
I-5	Benzyweed-lon
		I-5	Vanilla-Royle
I-5	Allicamide
		I-5	Picaodan
I-5	II e-5
		I-5	II e-11
I-6	Cloquintocet-mexyl
		I-6	Fenchlorazole
I-6	Biphenyl oxazole acid
		I-6	Pyrazolyl cloquintocet-mexyl
I-6	Grass-decomposing oxazole
		I-6	Fenclorim
I-6	Benzyweed-lon
		I-6	Vanilla-Royle
I-6	Allicamide
		I-6	Picaodan
I-6	II e-5
		I-6	II e-11

The compounds of the formulA (II A) used as safeners are known compounds and/or can be prepared by methods known per se (cf. WO-A-9I/07874, WO-A-95/07897).

The compounds of the general formulｃA (II b) used as safeners are known compounds and/or can be prepared by methods known per se (cf. EP-A-191736).

The compounds of the formula (II c) used as safeners are known compounds and/or can be prepared by methods known per se (cf. DE-A-2218097, DE-A-2350547).

The compounds of the formulA (II d) used as safeners are known compounds and/or can be prepared by methods known per se (cf. DE-A-19621522/US-A-6235680).

The compounds of the general formulA (II e) used as safeners are known compounds and/or can be prepared by methods known per se (cf. WO-A-99/66795/US-A-6251827).

Surprisingly, it has now been found that active compound combinations of substituted aryl ketones of the general formula (I) as defined above with safeners (antidotes) of the abovementioned part (b) have good insecticidal and/or acaricidal activity, while having very good compatibility with the useful plants, and can be used for the selective control of insects in a wide variety of crops, in particular cereals (in particular barley), but also millet, maize and rice.

In the present invention it is considered surprising that from a large number of known safeners or antidotes which are capable of combating the damaging effects of herbicides on crops, it has been found that in particular the compounds of part (b) above almost completely eliminate the damaging effects of substituted cyclic dicarbonyl compounds of formula (I) on crops without adversely affecting insecticidal and/or acaricidal activity.

Furthermore, it is also to be considered quite surprising that the compounds of section (b) above not only eliminate the damaging effect of the substituted cyclic dicarbonyl compounds of formula (I) on crop plants almost completely, but in some cases even enhance the insecticidal and/or acaricidal activity of the cyclic dicarbonyl compounds of formula (I), so that a synergistic effect is observed.

It is emphasized that particularly preferred and most preferred combination partners of part (b) have particularly advantageous pharmacological effects, in particular with regard to the harmlessness of cereal plants, such as wheat, barley and rye, and crops such as millet, maize and rice.

Combinations of active compounds can be used in general, for example, in the following plants:

dicotyledonous crops of the following genera:cotton (Gossypium), soybean (Glycine), beet (Beta), carrot (Daucus), Phaseolus (Phaseolus), pea (Pisum), Solanum (Solanum), flax (Linum), Ipomoea (Ipomoea), vetch (Vicia), Nicotiana (Nicotiana), tomato (Lycopersicon), peanut (arachi), Brassica (Brassica), Lactuca (Lactuca), Cucumis (Cucumis), cubitu, sunflower (helniahus).

Monocotyledonous crops of the following genera:oryza (Oryza), Zea (Zea), Triticum (Triticum), Hordeum (Hordeum), Avena (Avena), Secale (Secale), Sorghum (Sorghum), Panicum (Panicum), Saccharum (Saccharum), Ananas (Ananas), Asparagus (Asparagus), Allium (Allium).

However, the use of active compound combinations is in no way restricted to the above genera, but extends in the same way to other plants.

The advantageous effect of the active compound combinations is particularly pronounced at certain concentration ratios. However, the weight ratio of active compound in the active compound combination can also be varied within wide limits. Generally, from 0.001 to 1000 parts by weight, preferably from 0.01 to 100 parts by weight, particularly preferably from 0.05 to 10 parts by weight and most preferably from 0.07 to 1.5 parts by weight of one of the compounds (antidotes/safeners) which improve crop compatibility in (b) described above are present per part by weight of active compound of the formula (I) or a salt thereof.

The active compounds or active compound combinations can be converted into the customary formulations, for example solutions, emulsions, wettable powders, suspensions, dusts, powders, pastes, soluble powders, granules, suspoemulsion concentrates, natural and synthetic substances impregnated with active compound, and microcapsules in polymers.

The formulations are prepared in a known manner, for example by mixing the active compounds with extenders, that is, liquid solvents and/or solid carriers, optionally with the use of surfactants, that is, emulsifiers and/or dispersants, and/or foam formers.

If the filler used is water, it is also possible, for example, to use organic solvents as cosolvents. Suitable liquid solvents are mainly: aromatic compounds such as xylene, toluene or alkylnaphthalene; chlorinated aromatic or chlorinated aliphatic hydrocarbons, such as chlorobenzene, vinyl chloride or dichloromethane; aliphatic hydrocarbons, for example cyclohexane or paraffins, such as mineral oil fractions, mineral oil and vegetable oil; alcohols, such as butanol or ethylene glycol and ethers and esters thereof; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone; strongly polar solvents such as dimethylformamide and dimethylsulfoxide; and water.

Suitable solid carriers are:

for example ammonium salts, comminuted natural minerals such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and comminuted synthetic materials such as highly comminuted silica, alumina and silicates; suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, and also synthetic particles of inorganic and organic flours, and particles of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks; suitable emulsifiers and/or foaming agents are: for example nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and protein hydrolysates; suitable dispersants are: such as lignin sulfite waste liquor and methyl cellulose.

Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, and also natural phospholipids such as cephalins and lecithins and synthetic phospholipids, can be used in the formulations. Other additives may be mineral and vegetable oils.

Colorants such as inorganic pigments, for example iron oxide, titanium oxide and prussian blue, and organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.

The formulations generally contain from 0.1 to 95% by weight, preferably from 0.5 to 90% by weight, of active compound, including active compounds having a safety effect.

The active compound combinations are generally administered in the form of ready-to-use formulations. However, the active compounds contained in the active compound combinations may also be used in the form of separate preparations which are mixed in use, i.e. in the form of a canned mixture.

The active compound combinations can also be used as such or in the form of their formulations, or else in admixture with other known herbicides in the form of ready-to-use formulations or canned mixtures. It can also be in admixture with other known active compounds, for example fungicides, insecticides, acaricides, nematicides, attractants, disinfectants, bactericides, bird repellents, growth regulators, plant nutrients and soil conditioners. For certain applications, in particular by post-emergence methods, it may also be advantageous to include the following further additives in the formulation: vegetable or mineral oils with plant compatibility (e.g. "Rako Binol" as a commercial product), or ammonium salts, such as ammonium sulphate or ammonium thiocyanate.

The active compound combinations can be administered as such, in the form of their formulations or in the use forms prepared from the formulations by further dilution, for example ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. Application is effected in the customary manner, for example by pouring, spraying, atomizing, dusting or broadcasting.

The application rate of the active compound combinations can vary within certain limits; the rate of application depends, among other factors, primarily on weather and soil factors. In general, the application rate is from 0.005 to 5kg per hectare, preferably from 0.01 to 2kg per hectare, particularly preferably from 0.05 to 1.0kg per hectare.

The active compound combinations can be applied both before emergence of the plants and after emergence of the plants, i.e. both by the pre-emergence method and by the post-emergence method.

Depending on their nature, the safeners to be used can be used for pretreating the seed of the crop (dressing), or can be placed in the seed furrow before sowing (seed weeds), or can be used with the herbicide before or after emergence of the plant.

The active compound combinations are suitable for controlling animal pests, preferably arthropods and nematodes, in particular insects and arachnids, which are encountered in agriculture, in animal health, in forests, in stored products and in the protection of materials and in the hygiene sector. They are active against normally sensitive and resistant species and all or some stages of development. The pests include:

isopoda (Isopoda), for example, white-eared beetle (Oniscus asellus), Armadillium vulgare (Armadillidium vulgare) and Armadillidium globosum (Porcellio scaber).

From the order of the Diplopoda (Diplopoda), for example, Blaniulus guttulatus.

From the order of the Chilopoda (Chilopoda), for example, Geophilus carpophagus, Scutigerispp.

For general purposes (Symphyla), for example, Scutigerella immacula.

From the order of the Thysanura, for example, Chlamydomonas (Lepisma saccharana).

From the order of the Collelmola (Collelmbola), for example, Onychiurus armatus (Onychiurus armatus).

From the order of the Orthoptera (Orthoptera), for example, cricket-mae (Acheta domestica), Gryllotalpa spp, African migratory locusts (Locusta migratoriatoides), Black Locusta (Melanoplus spp), desert locusts (Schistocercagregaria).

From the order of the Blattaria (Blattaria), for example, Blatta orientalis (Blatta orientalis), Periplaneta americana (Periplaneta americana), Bladella maderae (Leucophaea germanae), Blatta germanica (Blattaria germanica).

From the Dermaptera (Dermaptera), for example, Forficula auricularia (Forficula auricularia).

From the order of the Isoptera (Isoptera), for example, Reticulitermes spp.

From the order of the Phtiaviridae (Phthiraptera), for example, Pediculus humanus (Pediculus humanus murroris), Pediculus humanus (Haematopinus spp.), Pediculus mucosus (Linogaphus spp.), Pediculus masticus (Trichoderma spp.), and Pediculus anidae (Damalinia spp.).

From the order of the Thysanoptera (Thysanoptera), for example, Thrips palmi (Hercinothrips femoralis), Thrips tabaci (Thrips tabaci), Thrips palmi (Thrips palmi), Thrips lucernifolia (Frankliniella occidentalis).

Heteroptera (Heteroptera), for example, Douglas bugs (Eurygaster spp.), Dysdercus intermedius, Blastus squaratus (Piesma quadrata), Cimex lecularius (Cimex lectularius), Nepholus longirostratus (Rhodnius prolixus), Nepholygus droguensis (Triatoma spp.).

Homoptera, for example, whitefly brassicae (Aleurodeses brassicae), whitefly cassava (Bemis tabaci), whitefly greenhouse (Trialeurodes vaporariorum), cotton aphid (Aphis gossypii), cabbage aphid (Brevicornus brassicae), Cryptosporidium theophyllum (Cryptomyces ribis), beet aphid (Aphis fabae), apple aphid (Aphis sphaeroides), apple woolly aphid (Eriosoma lanigerum), tail aphid (Hyalopterussuritus indusidinis), root nodule aphid (Phyllotreta), gall aphid (Pemphigus spp.), ductus avenae (Macrophyceae avenae), blast aphid (Phyllococcus laurentis), blast (Phyllococcus laurentii), blast furnace (Phyllococcus laurentis spp.), blast furnace leaf aphid (Phyllospirillus), blast furnace leaf blast (Phyllostachydis), blast (Phyllophora nigra), blast (Phyllophora), blast (Phosphaericoides), blast, Lepidoticus nigra (Lepidium), Piper grandis (Lepidium), Echinus (Lepidotis), Echinus (Lepidoticus), Echinus (Lepidotis sp), Echinus (Lepidotis), Echinus (Lepidotis, Phytopus), Echinus (Lepidotis), Echinus (Lepidotis, Echinus), Echinus (Lepidotis, Piercus), Echinus, Piercus), Echinus (Lepidotis, Piercus), Echinus, Piercus (Le, Pediculosis (Psylla spp.).

Lepidoptera (Lepidoptera), for example, Henropa sanguinea (Pectinophora gossypiella), Ectropis gigantea (Bupalus piniarius), Fangchi (Cheimatobirudoma), Spinidia pomonella (Lithocollectis blancardella), Plumeria pomonella (Hypomeuta padela), Plutella xylostella (Plutella xylostella), Trichosporona fulvescens (Malacospora neospora), yellow moth (Euproctis chrysospora), Potentilla (Lytrinia spp.), Cotton Endomastoma (Buccatrix thyristeriella), Phylophilus ostreatus (Phyllostachys nigra), Geotrichum (Agrostis spp.), Ceriporia virescens (Spirospodoptera), Sporidia sp., Sporidia spp (Sporidia spp.), Sporidia sp.), Sporidia falcata (Sporidia spp.), Sporidia sp., Sporidia spp), Sporidia spp (Sporidia spp.), Sporidia spp., Sporidia spp (Sporidia spp.), Sporidia spp., Sporidia spp (Sporidia spp.), Sporidia spp. (Sporidia spp.), Sporidia spp. (Sporidia, Curtain rice moth (Tineola bisseliella), bag rice moth (Tineoa pellionella), brown moth (Hofmonophila subcoudospora), yellow cabbage moth (Cacoecia podana), Capuarictoria, Colostrinia (Choristoneura fumerisana), grape fruit moth (Clysia ambiguella), tea leaf roller moth (Homona magnania), oak green roller moth (Tortrix viridana), Cnaphalocerus spp.

Coleoptera, for example, bark beetles (Anobium punctatum), bark beetles (Rhizopertha dominica), yellow bean weevil (Bruchidia), bean weevil (Acanthoscelides obtatus), Dolichos domestica (Hylotalpus), Pyrola giganteus (Agrimonia albus), Bubrotica (Agrimonia solani), Bupleura decemlineata (Leptospira decemlineata), Horseradix armenii (Eben. cochleariae), Diabrotica (Diabrotica spp.), Bupleuropyrophylla brassica (Psyllides chrysospora), Spanisum japonicum (Epilaphiophytum), Spira variola (Epilanthis), Atlanta spp Arachnoid (Ptinus spp.), yellow spider beetle (niptospiroucus), naked spider beetle (gibbsium psiloides), parvallia (tribolium spp.), yellow mealworm (Tenebrio molitor), click beetle (Agriotes spp.), broad chest click beetle (condereus spp.), western pentamonth gill (Melothalamolontha), potato gill horn (amphenglottilia), brown new zealand gill horn (Costelytra zealandica), and rice root elephant (lissorthophorus oryzae).

From the order of the Hymenoptera (Hymenoptera), for example, from the genus Trichoplusia (Diprion spp.), the genus Vespa (Hoplocpa spp.), the genus Maclea (Lasius spp.), the genus Melissa (Monomoumpharaonis), and the genus Vespa (Vespa spp.).

Diptera (Diptera), for example, Aedes (Aedes spp.), anopheles (anopheles spp.), Culex (Culex spp.), Drosophila melanogaster (Drosophila melanogaster), Musca (Musca spp.), latanidae (Fannia spp.), callimastix (calliphora erythrepha), Drosophila (Lucilia spp.), chrysomyzidae (chrysomyzilla spp.), xanthocera (cuteria spp.), gastrophila (gastrophilia spp.), hypecopia spp.), copora spp., hylotepa spp., hylocereus (hylocereuses spp.), pyricularia (ostrinia spp.), pyricularia spp.), cophaga (hylotepa spp.), pyricularia (hylotella spb), callitrichia (phyllospora spp.), pyricularia (ostrea spp.), pyricularia sp., echinacea (phylum spp.), pyricularia, callis (ostrea), callimastia (ostrinia spp.), pyricularia (ostrea), calli (ostrea spp.), pyricularia (ostrea), pyricularia (echinacea, echinus spp.), pyricularia (echinacea, echinus (echinus spp.), pyricularia (echinacea, echinus spp.), pyricularia (purpura) and pyricularia (penaeta).

Siphonaptera (Siphonaptera), for example, Xenopsylla cheopis (Xenopsylla cheopis), Ceratophyllus spp.

Arachnids, for example, the species Ceratopteris nipponensis (Scorpio maurus), Aranea nigripes (Latridectrus mactrans), Dermatophagoides farinae (Acarus sruro), Argassp (Argassp.), Bluella (Ornithiodosos spp.), Dermanyssus gallinarum (Dermanyssus gallinae), Scirpus latifolius (Eriophysphyes ribacteris), Phyllophora citrifolia (Phyllophora), Bull (Boophilus spp.), Rhipicephalus (Rhipicephalus lupussp.), Amblymoma sp., Taraxacum (Hyalomma spp.), Spp (ixodermatophagus spp.), Dermatophagus sp., Brucella (Thorophys spp.), Tetranysfos spp., Sarcophagus sp., Tetranysfos sp., Chloromyces spp., Tetranysfos sp., Tetranysfos (Tetranysfos spp.), Tetranysfos spp., Tetranysfos sp., Tetranysfos (Tetranysfos sp.), Tetranysfos sp., Tetranysfos (Tetranysfos sp.), and Tetranysfos sp.).

Plant parasitic nematodes include, for example, Pratylenchus spp, Radopholus similis, hedyotis herbacea (Ditylenchus dipsaci), hemithora nematoda (Tylenchus semipenetans), Heterodera (Heterodera spp), Globodera (Globodera spp), Meloidogyne (Meloidogyne spp), Globodera (Aphelenchides spp), Longidoxus (Looideus spp), Globodera (Xipelema spp), Trichopodiscus (Trichlororus spp), and Globodera (Burserpyschynia spp).

When used as insecticides in their commercially available formulations and in the use forms prepared from them, the active compounds can also be present in the form of a mixture with synergists. A synergist is a compound that enhances the activity of an active compound, but does not necessarily have activity on its own.

The active compound content of the use forms prepared from the commercially available formulations can vary within wide limits. The active compound concentration of the use forms can be from 0.0000001 to 95% by weight of active compound, preferably from 0.0001 to 1% by weight.

Application is carried out in a conventional manner suitable for the form of use.

All plants and plant parts can be treated according to the invention. Plants are to be understood as meaning all plants and plant populations, for example desired and undesired wild plants or crops (including naturally occurring crops). The crop plants can be plants which are obtained by conventional plant breeding and optimization methods or by biotechnological and genetic engineering methods or by combinations of these methods, including the transgenic plants, but also including the plant cultivars which are protected or not protected by plant breeders' rights. Plant parts are to be understood as meaning all parts and organs of the plant above and below the ground, such as shoots, leaves, flowers and roots, examples which may be mentioned being leaves, needles, stems, flowers, fruit bodies (fruit-bodies), fruits, seeds, roots, tubers and rhizomes. Plant parts also include harvests, as well as vegetative and generative propagation material, such as, for example, seedlings, tubers, rhizomes, cuttings and seeds.

The treatment of plants and plant parts with active compounds according to the invention is carried out directly or by allowing the compounds to act on the surroundings, habitat or storage space by conventional treatment methods, for example by soaking, spraying, evaporating, atomizing, broadcasting, painting on (broushing-on), and also, in the case of propagation material, in particular seeds, by applying one or more layers.

As mentioned above, all plants and parts thereof can be treated according to the invention. In a preferred embodiment, wild plant species and plant varieties, or varieties obtained by conventional biological breeding methods, for example by crossing or protoplast fusion, as well as parts of said plant varieties, are treated. In a more preferred embodiment, transgenic plants and plant varieties (genetically modified organisms) and parts thereof obtained by genetic engineering, if appropriate in combination with conventional methods, are treated. The term "part" or "part of a plant" or "plant part" is to be construed as above.

Particularly preferred plants to be treated according to the invention are the respective commercially available or used plant varieties.

Depending on the plant species or plant variety, its location and growth conditions (soil, climate, vegetation period, nutrition), the treatment of the invention may also produce superadditive ("synergistic") effects. This can lead to effects which are beyond the actual expectations, for example a reduction in the application rate and/or a widening of the activity spectrum and/or an increase in the activity of the substances and compositions which can be used according to the invention, an improvement in the growth of the plants, an increase in the tolerance to high or low temperatures, an increase in the tolerance to drought or to water or soil salt content, an increase in the flowering performance, an easier harvesting, an accelerated maturation, an increase in the yield, an increase in the quality and/or the nutritional value of the harvested products, an improvement in the storage stability of the harvested products and/or in their processability.

Preferred transgenic plants or plant varieties to be treated according to the invention, i.e.obtained by genetic engineering, include all plants which, in the genetic modification, receive genetic material which confers particularly advantageous useful properties on the plant in question. Examples of such properties are improved plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, increased yield, increased quality and/or increased nutritional value of the harvested products, improved storage stability and/or processability of the harvested products. Further examples of such properties, which are to be particularly emphasized, are improved plant resistance to animal and microbial pests, for example to insects, mites, phytopathogenic fungi, bacteria and/or viruses, and increased plant tolerance to certain herbicidally active compounds. Examples of transgenic plants which may be mentioned are important crops, such as cereals (wheat, rice), maize, soya beans, potatoes, cotton, oilseed rape (oilseed rape) and fruit plants (the fruits are apples, pears, citrus fruits)And grapes), particular emphasis is given to corn, soybean, potato, cotton, and oilseed rape. A particularly emphasized property is the increased resistance of plants to insects by forming toxins within the plant, in particular toxins formed within the plant by the genetic material of Bacillus thuringiensis, for example by the genes Cry IA (a), Cry IA (B), Cry IA (c), Cry IIA, Cry III A, Cry III B2, Cry9c, Cry2Ab, Cry3Bb and Cry IF and combinations thereof (hereinafter referred to simply as "Bt plants"). Other properties which are particularly emphasized are the increased tolerance of the plants to certain herbicidally active compounds, for example imidazolinones, sulphonylureas, glyphosate (e.g.the "PAT" gene) or phosphinotricin. The genes in question which confer the desired properties can also be combined with one another in the transgenic plants. An example of a "Bt plant" that may be mentioned is the commercial trade name YIELD(e.g., corn, cotton, soybean),

(e.g., corn),

(e.g., corn),

(cotton),

(Cotton) and

maize varieties, cotton varieties, soybean varieties, and potato varieties. An example of a plant with herbicide tolerance that may be proposed is the commercially available plant under the trade name Roundup(having glyphosate tolerance, e.g. corn)Cotton, soybean), Liberty

(tolerant to phosphinotricin, e.g. oilseed rape),(having imidazolinone tolerance) and

maize varieties, cotton varieties and soybean varieties (with sulfonylurea tolerance, e.g. maize). Plants with herbicide resistance (plants bred in a conventional herbicide-tolerant manner) that may be proposed also include the so-calledA commercially available variety of (e.g., maize). Of course, the above statements also apply to plant varieties having the genetic characteristics described or to be developed, which plant varieties will be developed and/or marketed in the future.

The plants mentioned above can be treated particularly advantageously according to the invention with a mixture of active compounds. The preferred ranges for the above mixtures also apply to the treatment of said plants. Particular emphasis is given to the treatment of plants with the mixtures specifically proposed according to the invention.

Application examples

Preparation of 20WS formulation and subsequent dressing

The amounts of safener and active compound required to prepare a 20WS formulation were dissolved in acetone in an agate mortar and the appropriate amount of the formulation without active compound (actually used to prepare Gaucho70WS) was added. The mixture was dried until only a small amount of residual moisture could be detected. The material was carefully separated from the bowl wall using a spatula and the material was crushed in a mortar to dryness. The experimental preparation prepared as above, in an amount appropriate to the amount of seed to be dressed, was filled into a beaker having a size so large that the seed filled at most one third of it during dressing. Sufficient water is added (depending on the nature of the seed surface). The seeds are then filled into beakers containing the formulation and water and dressed on a test tube shaker by means of a spatula or glass rod. After the preparation has been distributed as uniformly as possible on the seeds, the seeds are dried in a fume hood.

Testing in seed trays

31 plastic trays (20X 5cm) were filled with sandy loam. The soil is compacted using a punch to the depth of the stack required for the crop under study. 20 seeds were sown at regular intervals in each seed tray by tweezers and buried in soil using the above punch. The test container was placed in a greenhouse and the surface was slowly compacted again using a punch. In addition to the test substance, an untreated control sample was also tested. Each variant employs at least 2 discs. The seed discs were watered and covered with film until the plants emerged. After emergence, the seed disks were watered twice daily. Evaluation was carried out by counting the number of plants that have germinated and determining the damage (expressed in%) by comparison with untreated controls 5-14 days after sowing.

Greenhouse test results for safener after dressing:

example I-1

Known from WO 03/029213, example No. I-1-c-11

TABLE A

TABLE B

Watch C

The method comprises the following steps: post-spray safener testing

Modification a)

Solvent: 7 parts by weight of DMF

Emulsifier: 2 parts by weight of an alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with tap water to the desired concentration. The required amount of safener (WP 20 for mefenpyr) was mixed into the dilution water. In addition, 2g active ingredient/l rape oil methyl ester 500EW was added. Leaves of winter barley in the 2-leaf stage infested with the aphid glonaschium graminifolium (Rhopalosiphum padi) were treated by means of a spray boom with the desired concentration of active compound and safener, the water application rate being 300 l/ha. For each deformation protocol, the test was performed at least twice. Evaluation was carried out by determining the percentage damage of the plants after 7 and/or 14 days, wherein both the percentage damage of the treated and the new plants and the percentage mortality of the cereal aphids were evaluated by comparison with the untreated control. 100% damage means plant death, and 0% means no damage. A 100% efficacy on grain aphids indicates that all aphids are killed; 0% means that no aphids were killed.

Variant b)

In variant b), the active compound is applied in the form of an SC preparation in a mixture with mefenpyr-diethyl WP20 and 2g of active ingredient per liter of rape seed methyl ester 500EW at the same desired concentration as in variant a). The implementation and evaluation were carried out as described in variant a).

Greenhouse test result of safener after spraying on wheat grain aphid in sinonovacula constricta in winter

Examples I-1 to 2

Known from WO 03/029213, example No. I-1-a-9

Table D(modification b)

TABLE E(modification b)

TABLE F(modification b)

Watch G(modification a)

Watch H(modification a)

Formula for calculating mortality of two active compound combinations

The expected activity of a given combination of two active compounds can be determined in terms of S.R. Colby, Weeds15(1967) Pages 20-22, as follows:

if it is

X is at the application ratemg/ha or in concentrationmThe mortality rate in ppm of the active compound A administered,

y is at the application rateng/ha or in concentrationnThe mortality rate in ppm of the active compound B applied,

e is at the application ratemg/ha andng/ha or in concentrationmppm andnthe mortality rate in ppm of the active compounds A and B applied,

then

<math> <mrow> <mi>E</mi> <mo>=</mo> <mi>X</mi> <mo>+</mo> <mi>Y</mi> <mo>-</mo> <mfrac> <mrow> <mi>X</mi> <mo>&CenterDot;</mo> <mi>Y</mi> </mrow> <mn>100</mn> </mfrac> <mo>.</mo> </mrow></math>

In the present invention, mortality is measured as a percentage. 0% indicates an equivalent mortality rate to the control, while 100% mortality indicates no infection was observed.

If the actual mortality is higher than the calculated value, the activity of the conjugate is superadditive, i.e., there is a synergistic effect. In this case, the actual observed mortality rate must exceed the expected mortality rate (E) calculated using the above equation.

Spray application examples

Solvent: water (W)

Auxiliary agent: rape oil methyl ester (0.1% active ingredient/liter)

To prepare a suitable application solution, 1 part by weight of the formulation is mixed with the appropriate amounts of water and auxiliaries and the concentrate is diluted with water to the desired concentration.

Example I

Aphis gossypii test

Grass cotton (gossypium herbaceum) heavily infested by cotton aphid (Aphis gossypii) is sprayed to the point of runoff point with an application solution of the desired concentration.

Example J

Myzus test

Bell peppers (Capsicumsativum) heavily infested by the green peach aphid (Myzus persicae) were sprayed to the runoff point with the application solution of the desired concentration.

Example K

Wheat non-net aphid test

Barley (Hordeum vulgare) heavily infested by the aphid metopodium dirhodium is sprayed to the point of run-off with the application solution of the desired concentration.

After the desired time, the percent mortality was determined. 100% means that all aphids are killed; 0% means that no aphids were killed. The measured mortality was substituted into Colby's formula.

In this test, for example, the following active compound combinations according to the present application show a synergistically enhanced activity compared with the active compounds administered alone:

TABLE I

Insect harmful to plant

Aphis gossypii test

^*Measured value is the activity actually measured

^**Calculated value ═ Activity calculated using Colby formula

TABLE I (continuation)

Insect harmful to plant

Aphis gossypii test

^*Measured value is the activity actually measured

^**Calculated value ═ Activity calculated using Colby formula

TABLE J

Insect harmful to plant

Myzus test

^*Measured values are the activity actually measured,^**calculated value ═ Activity calculated using Colby formula

Watch K

Insect harmful to plant

Wheat non-net aphid test

^*Measured value is the activity actually measured

^*Calculated value ═ activity calculated using Colby formula

Example L

Critical concentration test/soil insect-transgenic plant treatment

Testing insects: cucumber streak (Diabrotica balteata) -larvae in soil

Solvent: 7 parts by weight of acetone

Emulsifier: 1 part by weight of an alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound and the stated amount of solvent are mixed, the stated amount of emulsifier is added, and the concentrate is diluted with water to the desired concentration.

The active compound preparation is poured onto the soil. The concentration of active compound in the preparation is not critical in practice here, but only the weight of active compound per unit volume of soil (expressed in ppm (mg/l)). The soil was filled in 0.251 pot and left to stand at 20 ℃.

Immediately after the preparation process, 5 pregerminated cultivar YIELDGUARD (trademark of Monsanto, USA) corn (maize corn) was placed in each pot. After 2 days, the corresponding test insects were placed in the treated soil. After a further 7 days, the potency of the active compounds was determined by counting the number of maize plants that had germinated (1 plant-20% activity).

Example M

Tobacco budworm (Heliothis virescens) test-transgenic plant treatment

Solvent: 7 parts by weight of acetone

Emulsifier: 1 part by weight of an alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.

Seedlings of the cultivar Roundup Ready (trademark of Monsanto, USA) soybean (Glycinemax) were treated by dipping them in the preparation of active compound of the desired concentration and inoculated with the tobacco budworm while the leaves were still moist.

After the desired time, the death of the insect was determined.

Claims (7)

1. Use of compositions containing an effective amount of active compound combinations containing

(a) At least one compound of formula (I)

Wherein,

w represents C₁-C₆An alkyl group, a carboxyl group,

x represents C₁-C₆An alkyl group, a carboxyl group,

y represents a halogen atom or a halogen atom,

z represents a hydrogen atom or a hydrogen atom,

CDC represents the following group

Wherein,

a and B together with the carbon atom to which they are attached represent saturated, unsubstituted or substituted by C₁-C₈C substituted by alkoxy, optionally with one ring atom replaced by oxygen or sulphur₃-C₁₀A cycloalkyl group,

d represents hydrogen, and the compound (D) represents hydrogen,

g represents halogen;

and

(b) at least one crop compatibility-improving compound selected from the group consisting of:

the cloquintocet-mexyl is prepared from cloquintocet-mexyl,

and/or one of the following compounds defined by the general formula,

general formula (IIb)

Wherein

A²Represents an alkanediyl group having 1 or 2 carbon atoms,

R⁹represents hydroxy or C₁-C₆An alkoxy group,

X²represents hydrogen or a halogen, and is,

X³represents hydrogen.

2. Use according to claim 1 for controlling insects using a composition comprising a compound of formula (I),

wherein,

A. b together with the carbon atom to which they are attached represents wherein optionally one ring atom is replaced by oxygen or sulphur and optionally by C₁-C₈Alkoxy mono-or disubstituted saturated C₃-C₁₀Cycloalkyl radicals，

G represents chlorine or bromine.

3. Use according to claim 1 for controlling insects using a composition comprising a compound of formula (I),

wherein,

w represents C₁-C₃An alkyl group, a carboxyl group,

x represents C₁-C₄An alkyl group, a carboxyl group,

y represents chlorine or bromine,

A. b together with the carbon atom to which they are attached represents wherein optionally one ring atom is replaced by oxygen or sulphur and optionally by C₁-C₄Alkoxy monosubstituted saturated C₃-C₇A cycloalkyl group,

g represents chlorine.

4. Use according to claim 1 for controlling insects using a composition comprising a compound of formula (I),

wherein,

w represents a methyl group or an ethyl group,

x represents a methyl, ethyl or propyl group,

y represents chlorine or bromine,

A. b together with the carbon atom to which they are attached represents saturated C wherein optionally one ring atom is replaced by oxygen and optionally monosubstituted by methoxy, ethoxy, propoxy, butoxy or isobutoxy₅-C₆A cycloalkyl group,

g represents chlorine.

5. Use according to claim 1 for controlling insects using a composition comprising a compound of formula (I),

wherein,

w represents a methyl group or an ethyl group,

x represents a methyl, ethyl or propyl group,

y represents chlorine or bromine,

A. b together with the carbon atom to which they are attached represents whereinSaturated C wherein one ring atom is replaced by oxygen and optionally monosubstituted by methoxy, ethoxy, propoxy, butoxy or isobutoxy₅-C₆A cycloalkyl group,

g represents chlorine.

6. Method for controlling insects and/or arachnids, characterized in that a composition as defined in claim 1 is allowed to act on the insects and/or arachnids and/or their habitat.

7. Use of a composition according to claim 1 for controlling insects and/or arachnids, wherein the compound which improves the action compatibility is cloquintocet-mexyl.