AU2005263566A1 - Selective insecticides and/or acaricides based on substituted, cyclic dicarbonyl compounds and safeners - Google Patents

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

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AU2005263566A1
AU2005263566A1 AU2005263566A AU2005263566A AU2005263566A1 AU 2005263566 A1 AU2005263566 A1 AU 2005263566A1 AU 2005263566 A AU2005263566 A AU 2005263566A AU 2005263566 A AU2005263566 A AU 2005263566A AU 2005263566 A1 AU2005263566 A1 AU 2005263566A1
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alkyl
optionally
alkoxy
methyl
represents hydrogen
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AU2005263566A
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Christian Arnold
Reiner Fischer
Udo Reckmann
Chris Rosinger
Erich Sanwald
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Bayer CropScience AG
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Bayer CropScience AG
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    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N33/00Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/16Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
    • A01N33/18Nitro compounds
    • A01N33/20Nitro compounds containing oxygen or sulfur attached to the carbon skeleton containing the nitro group
    • A01N33/22Nitro compounds containing oxygen or sulfur attached to the carbon skeleton containing the nitro group having at least one oxygen or sulfur atom and at least one nitro group directly attached to the same aromatic ring system
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/32Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N33/00Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N33/00Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/16Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A01N43/38Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Description

IN THE MATTER OF an Australian Application corresponding to PCT Application PCT/EP2005/007790 RWS Group Ltd, of Europa House, Marsham Way, Gerrards Cross, Buckinghamshire, England, hereby solemnly and sincerely declares that, to the best of its knowledge and belief, the following document, prepared by one of its translators competent in the art and conversant with the English and German languages, is a true and correct translation of the PCT Application filed under No. PCT/EP2005/007790. Date: 3 January 2007 N. T. SIMPKIN Acting Deputy Managing Director For and on behalf of RWS Group Ltd -1 Selective insecticides and/or acaricides based on substituted, cyclic dicarbonvl compounds and safeners The invention relates to the use of selective insecticidal and/or acaricidal active compound combinations comprising firstly substituted cyclic dicarbonyl compounds and secondly at least 5 one crop plant compatibility-improving compound, which combinations can be used for the selective control of insects and/or spider mites in various crops of useful plants. It is known that 4-chloro- und 4-nitro-4-phenyl-pyrazolyl-3,5-diones (WO 99/206 10) have herbicidal action and that 3-halo- and 3-nitro-3-phenyl-substituted pyrrolidine-2,4-diones and 4-oxofuran-2-ones (JP-A 12 086 628) have acaricidal and insecticidal action, and also 10 herbicidal, acaricidal and insecticidal action (WO 03/029 213, DE-A 103 01805, WO 03/045 957, WO 2004/069 841). Also known are 2-chloro-2-phenylcyclopentane-1,3-diones and 2-chloro-2-phenylcyclohexane 1,3-diones from WO 2004/037 749. Likewise known are 4-chloro-4-phenylpyrazolidine-3,5-diones having herbicidal and 15 insecticidal/acaricidal action from WO 2005/016 933. Moreover, selective herbicides based on substituted cyclic dicarbonyl compounds and safeners have been described (WO 2004/064 520). However, the compatibility of these compounds in particular with monocotyledonous crop plants is not under all conditions entirely satisfactory. 20 Surprisingly, it has now been found that certain substituted cyclic dicarbonyl compounds, when used together with the crop plant compatibility-improving compounds (safeners/antidotes) described below, prevent damage to crop plants extremely well and can be used particularly advantageously as broad-spectrum combination preparations for the selective control of insects even in crops of monocotyledonous useful plants, such as, for example, in 25 cereals. The invention provides the use of selective insecticidal and/or acaricidal compositions comprising an effective amount of an active compound combination comprising, as components (a) at least one substituted cyclic dicarbonyl compound of the formula (1) -2 x Y CDC Z W in which W and Z independently of one another represent hydrogen, halogen, alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, haloalkyl, haloalkoxy, haloalkenyloxy, nitro or cyano, 5 X represents halogen, alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkylthio, alkylsulphinyl, alkylsulphonyl, haloalkyl, haloalkoxy, haloalkenyloxy, nitro or cyano, Y represents hydrogen, halogen, alkyl, haloalkyl, haloalkoxy, nitro, cyano or represents optionally substituted phenyl or hetaryl, 10 CDC represents one of the groups o 0 A A B (1), B (2), - G G D O O A A, N B (3), (4) S G ,N G O D O 0 0 A A B (5) or B G (6), Q \G Q 4 O Q2 0 Q 6 in which 15 A represents hydrogen, in each case optionally halogen-substituted alkyl, -3 alkenyl, alkoxyalkyl, alkylthioalkyl, saturated or unsaturated, optionally substituted cycloalkyl in which optionally at least one ring atom is replaced by a heteroatom, or in each case optionally halogen-, alkyl-, haloalkyl-, alkoxy-, haloalkoxy-, cyano- or nitro-substituted aryl, arylalkyl or hetaryl, 5 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 cycle which optionally contains at least one heteroatom, D represents hydrogen or an optionally substituted radical from the group 10 consisting of alkyl, alkenyl, alkynyl, alkoxyalkyl, saturated or unsaturated cycloalkyl in which optionally one or more ring members are replaced by heteroatoms, arylalkyl, aryl, hetarylalkyl or hetaryl or A and D together with the atoms to which they are attached represent a saturated or unsaturated cycle which is unsubstituted or substituted in the A,D moiety 15 and optionally contains at least one heteroatom, or A and Q' together represent alkanediyl or alkenediyl optionally substituted by hydroxyl or by in each case optionally substituted alkyl, alkoxy, alkylthio, cycloalkyl, benzyloxy or aryl, or
Q
1 represents hydrogen or alkyl, 20 Q 2 , Q 4 , Qs and Q 6 independently of one another represent hydrogen or alkyl,
Q
3 represents hydrogen, alkyl, alkoxyalkyl, alkylthioalkyl, optionally substituted cycloalkyl (in which optionally one methylene group is replaced by oxygen or sulphur) or optionally substituted phenyl, or
Q
3 and Q 4 together with the carbon atom to which they are attached represent a 25 saturated or unsaturated, unsubstituted or substituted cycle which optionally contains a heteroatom, G represents halogen or nitro, including all isomeric forns, -4 and (b) at least one crop plant compatibility-improving compound from the following group of compounds: 4-dichloroacetyl-l-oxa-4-azaspiro[4.5]decane (AD-67, MON-4660), I-dichloroacetyl-hexa 5 hydro-3,3,8a-trimethylpyrrolo[ 1,2-a]pyrimidin-6(2H)-one (dicyclonon, BAS-145138), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H- l,4-benzoxazine (benoxacor), I -methylhexyl 5-chloroquinolin-8-oxyacetate (cloquintocet-mexyl - cf. also related compounds in EP-A 86750, EP-A-94349, EP-A-191736, EP-A-492366), 3-(2-chlorobenzyl)-l-(1-methyl-1 phenylethyl)urea (cumyluron), a-(cyanomethoximino)-phenylacetonitrile (cyometrinil), 2,4 10 dichlorophenoxyacetic acid (2,4-D), 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB), 1-(] methyl-I-phenylethyl)-3-(4-methylphenyl)urea (daimuron, dymron), 3,6-dichloro-2 methoxybenzoic acid (dicamba), S-1-methyl-I-phenylethyl piperidine- 1 -thiocarboxylate (dimepiperate), 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 15 phenylpyrimidine (fenclorim), ethyl 1-(2,4-dichlorophenyl)-5-trichloromethyl-IH-1,2,4 triazole-3-carboxylate (fenchlorazole-ethyl - cf. also related compounds in EP-A-174562 and EP-A-346620), phenylmethyl 2-chloro-4-trifluoromethylthiazole-5-carboxylate (flurazole), 4-chloro-N-(1,3-dioxolan-2-ylmethoxy)-a-trifluoroacetophenone oxime (fluxofenim), 3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyloxazolidine (furilazole, MON- 13900), ethyl 4,5 20 dihydro-5,5-diphenyl-3-isoxazolecarboxylate (isoxadifen-ethyl - cf. also related compounds in WO-A-95/07897), 1-(ethoxycarbonyl)ethyl-3,6-dichloro-2-methoxybenzoate (lactidichlor), (4-chloro-o-tolyloxy)acetic acid (MCPA), 2-(4-chloro-o-tolyloxy)propionic acid (mecoprop), diethyl 1-(2,4-dichlorophenyl)-4,5-dihydro-5-methyl-IH-pyrazole-3,5 dicarboxylate (mefenpyr-diethyl- cf. also related compounds in WO-A-91/07874), 2 25 dichloromethyl-2-methyl-1,3-dioxolane (MG-191), 2-propenyl-1-oxa-4-azaspiro[4.5]decane 4-carbodithioate (MG-838), 1,8-naphthalic anhydride, a-(I,3-dioxolan-2-yl methoximino)phenylacetonitrile (oxabetrinil), 2,2-dichloro-N-(1,3-dioxolan-2-ylmethyl)-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)butyric acid, 30 4-(4-chlorophenoxy)-butyric acid, diphenylmethoxyacetic acid, methyl diphenylmethoxyacetate, ethyl diphenylmethoxyacetate, methyl 1-(2-chlorophenyl)-5 phenyI-1H-pyrazole-3-carboxylate, ethyl 1-(2,4-dichlorophenyl)-5-methyl-1H-pyrazole-3 carboxylate, ethyl I-(2,4-d ich lorophenyl)-5-isopropyl- I H-pyrazole-3-carboxylate, ethyl I -(2,4-d ichlorophenyl)-5-( ,I 1-dimethylethyl)- 1 H-pyrazole-3-carboxylate, ethyl 1-(2,4- -5 dichlorophenyl)-5-phenyl-1H-pyrazole-3-carboxylate (cf. also related compounds in EP-A 269806 and EP-A-333131), ethyl 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate, ethyl 5-phenyl-2-isoxazol ine-3-carboxylate, ethyl 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3 carboxylate (cf. also related compounds in WO-A-91/08202), 1,3-dimethylbut-1-yl 5 5-chloroquinolin-8-oxyacetate, 4-allyloxybutyl 5-chloroquinolin-8-oxyacetate, I-allyl oxyprop-2-yl 5-chloroquinolin-8-oxyacetate, methyl 5-chloroquinoxalin-8-oxyacetate, ethyl 5-chloroquinolin-8-oxyacetate, allyl 5-chloroquinoxalin-8-oxyacetate, 2-oxoprop- I-yl 5-chloroquinolin-8-oxyacetate, diethyl 5-chloroquinolin-8-oxymalonate, diallyl 5-chloroquinoxalin-8-oxymalonate, diethyl 5-chloroquinolin-8-oxymalonate (cf. also related 10 compounds in EP-A-582198), 4-carboxy-chroman-4-ylacetic acid (AC-304415, cf. EP-A-613618), 4-chlorophenoxyacetic acid, 3,3'-dimethyl-4-methoxybenzophenone, I -bromo-4-chloromethylsulphonyl benzene, I-[4-(N-2-methoxybenzoylsulphamoyl)phenyl] 3-methylurea (alias N-(2-methoxybenzoyl)-4-[(methylam inocarbonyl)amino] benzene sulphonamide), 1-[4-(N-2-methoxybenzoylsulphamoyl)-phenyl]-3,3-dimethylurea, 1-[4-(N 15 4,5-dimethylbenzoylsulphamoyl)phenyl]-3-methylurea, I-[4-(N-naphthylsulphamoyl) phenyl]-3,3-dimethylurea, N-(2-methoxy-5-methylbenzoyl)-4-(cyclopropylaminocarbonyl) benzenesulphonamide, and/or one of the following compounds (defined by general formulae) of the general formula (Ila) (X20 A0 (Ia) 20R or of the general formula (Hb) X 3 X 2 N 0 OA2' R9 (11b) or of the formula (Hc) -6 0 I 11 where m represents a number 0, 1, 2, 3, 4 or 5, A] represents one of the divalent heterocyclic groups outlined hereinbelow, N R N N
R
15 0 OR 14 R 13 R13 5 0 n represents a number 0, 1, 2, 3, 4 or 5, A2 represents alkanediyl having 1 or 2 carbon atoms which is optionally substituted by C, -C 4 -alkyl and/or CI-C 4 -alkoxycarbonyl and/or , -C 4 -atkenyloxy-carbonyl, R8 represents hydroxyl, mercapto, amino, C,-C 6 -alkoxy, Cl-C6-alkylthio, C,-C 6 10 alkylamino or di-(C-C 4 -alkyl)amino,
R
9 represents hydroxyl, mercapto, amino, C-C 7 -alkoxy, Cl-C 6 -alkenyloxy, C-C 6 alkenyloxy-Ci -C 6 -alkoxy, C, -C 6 -alkylthio, C, -C 6 -alkylamino or di-(CI-C 4 -alkyl)amino, A20 represents C-C 4 -alkyl which is optionally substituted in each case by fluorine, chlorine and/or bromine, 15 R" represents hydrogen, or represents C,-C 6 -alkyl, C 2
-C
6 -alkenyl or C 2
-C
6 -alkynyl, Co-C 4 -alkoxy-C,-C 4 -alkyl, dioxolanyl-Cr-C 4 -alkyl, fury, furyi-C-C 4 -alkyl, thienyl, thiazolyl, piperidinyl, each of which is optionally substituted by fluorine, chlorine and/or bromine, or represents phenyl which is optionally substituted by fluorine, chlorine and/or bromine or C,-C 4 -alkyl, 20 R 2 represents hydrogen, or represents C-C 6 -alkyl, C 2
-C
6 -alkenyl or Cr-C 6 -alkynyl,
C,-C
4 -alkoxy-C -C 4 -alkyl, dioxolanyl-Cr-C 4 -alkyl, furyl, furyl-C-C 4 -alkyl, thienyl, thiazolyl, piperidinyl, each of which is optionally substituted by fluorine, chlorine and/or bromine, or represents phenyl which is optionally substituted by fluorine, -7 chlorine and/or bromine or Ci-C 4 -alkyl, or R" and R 12 together represent
C
3
-C
6 -alkanediyl or C 2
-C
5 -oxaalkanediyl, each of which is optionally substituted by
CI-C
4 -alkyl, phenyl, furyl, a fused benzene ring or by two substituents which, together with the C atom to which they are bonded, form a 5- or 6-membered 5 carbocycle, R represents hydrogen, cyano, halogen, or represents CI-C 4 -alkyl, C 3
-C
6 -cycloalkyl or phenyl, each of which is optionally substituted by fluorine, chlorine and/or bromine,
R
1 4 represents hydrogen, or represents CI-C 6 -alkyl, C 3
-C
6 -cycloalkyl or tri(CI-C 4 alkyl)silyl, optionally substituted by hydroxyl, cyano, halogen or CI-C 4 -alkoxy, 10 R" represents hydrogen, cyano, halogen, or represents CI-C 4 -alkyl, C 3
-C
6 -cycloalkyl or phenyl, each of which is optionally substituted by fluorine, chlorine and/or bromine, X1 represents nitro, cyano, halogen, CI-C 4 -alkyl, Cl-C 4 -haloalkyl, CI-C 4 -alkoxy or Ci-C 4 -haloalkoxy, X2 represents hydrogen, cyano, nitro, halogen, CI-C 4 -alkyl, C 1
-C
4 -haloalkyl, CI-C 4 15 alkoxy or Ci-C 4 -haloalkoxy, x3 represents hydrogen, cyano, nitro, halogen, CI-C 4 -alkyl, C,-C 4 -haloalkyl, C 1
-C
4 alkoxy or Cl-C 4 -haloalkoxy, and/or the following compounds (defined by general formulae) of the general formula (Ild) 0 N (X )
SO
2 (lid) 20 0 or of the general formula (Ie) -8 0 19 (X), R -N N R (lie) 1 20 1 X4 SO2 (Ile) 0 where t represents a number 0, 1, 2, 3, 4 or 5, v represents a number 0, 1, 2, 3, 4 or 5, 5 R16 represents hydrogen or CI-C4-alkyl, R represents hydrogen or Ci-C 4 -alkyl, R1 8 represents hydrogen, or represents C,-C 6 -alkyl, C 1
-C
6 -alkoxy, C-C 6 -alkylthio,
C
1
-C
6 -alkylamino or di-(Ci-C 4 -alkyl)amino, each of which is optionally substituted by cyano, halogen or Ci-C 4 -alkoxy, or represents C 3
-C
6 -cycloalkyl, C 3
-C
6 10 cycloalkyloxy, C 3
-C
6 -cycloalkylthio or C 3
-C
6 -cycloalkylamino, each of which is optionally substituted by cyano, halogen or Ci-C 4 -alkyl, R'9 represents hydrogen, or represents C 1
-C
6 -alkyl which is optionally substituted by cyano, hydroxyl, halogen or Cl-C 4 -alkoxy, or represents C 3
-C
6 -alkenyl or C 3
-C
6 alkynyl, each of which is optionally substituted by cyano or halogen, or represents 15 C 3
-C
6 -cycloalkyl which is optionally substituted by cyano, halogen or CI-C 4 -alkyl, R 20 represents hydrogen, or represents C 1
-C
6 -alkyl which is optionally substituted by cyano, hydroxyl, halogen or C 1
-C
4 -alkoxy, or represents C 3
-C
6 -alkenyl or CrC6 alkynyl, each of which is optionally substituted by cyano or halogen, or represents
C
3
-C
6 -cycloalkyl which is optionally substituted by cyano, halogen or Cl-C 4 -alkyl, 20 or represents phenyl which is optionally substituted by nitro, cyano, halogen, Ci-C 4 alkyl, Cl-C 4 -haloalkyl, Ci-C 4 -alkoxy or C 1
-C
4 -haloalkoxy, or together with R' 9 represents C 2
-C
6 -alkanediyl or C 2
-C
5 -oxaalkanediyl, each of which is optionally substituted by C,-C 4 -alkyl,
X
4 represents nitro, cyano, carboxyl, carbamoyl, formyl, sulphamoyl, hydroxyl, amino, 25 halogen, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, C-C 4 -alkoxy or Cl-C 4 -haloalkoxy, and -9
X
5 represents nitro, cyano, carboxyl, carbamoyl, formyl, sulphamoyl, hydroxyl, amino, halogen, CI-C 4 -alkyl, CI-C 4 -haloalkyl, Ci-C 4 -alkoxy or Ci-C 4 -haloalkoxy for controlling insects and/or arachnids. In the definitions, the hydrocarbon chains, such as in alkyl or alkanediyl, are in each case 5 straight-chain or branched - including in combination with heteroatoms, such as in alkoxy. Depending inter alia on the nature of the substituents, the compounds of the formula (I) can be present as geometrical and/or optical isomers or isomer mixtures of varying composition which, if appropriate, may be separated in a customary manner. The present invention provides both the pure isomers and the isomer mixtures, and also their use and compositions 10 comprising them. Hereinbelow, for the sake of simplicity, only compounds of the formula (I) are referred to in each case, although what is meant are both the pure compounds and, if appropriate, also mixtures having different proportions of isomeric compounds. Taking into account the meanings (1) to (6) of the group CDC, the following principal structures (I-I) to (1-6) result: O X O X A A B N (1-1), B (1-2), G Z G Z D 15 o W o W O X A 0 AA A -Y N B (1-3), z (1-4), S G z D/ G O W W X AO X B 0 Y B Y A z (1-5), A G Qi~ W (-) Q .2 G Z 6 Q O W 5 Q in which - 10 A, B, D, G, Q 1 , Q 2 , Q 3 , Q 4 , Qs, Q 6 , W, X, Y and Z are as defined above. The formula (I) provides a general definition of the substituted cyclic dicarbonyl compounds of the insecticidal and/or acaricidal compositions. Preferred substituents or ranges of the radicals given for the formulae mentioned above and below are illustrated below: 5 W and Z independently of one another preferably represent hydrogen, halogen, C-C 6 -alkyl,
C
1
-C
6 -haloalkyl or CI-C 6 -alkoxy, X preferably represents halogen, C-C 6 -alkyl, C 2
-C
6 -alkenyl, C 2
-C
6 -alkynyl, C-C 6 haloalkyl, C 1
-C
6 -alkoxy, C 3
-C
6 -alkenyloxy, C 1
-C
6 -haloalkoxy, C 3
-C
6 haloalkenyloxy, nitro or cyano, 10 Y preferably represents hydrogen, halogen, CI-C 4 -alkyl, CI-C 2 -haloalkyl, C-C 2 haloalkoxy, cyano or one of the radicals V V2 o 3 V 2 ,3 3 V S V3 S V2 in which 15 V 1 preferably represents hydrogen, halogen, C-C 12 -alkyl, CI-C 6 -alkoxy, C 1
-C
4 haloalkyl, Cr-C 4 -haloalkoxy, nitro or cyano,
V
2 and V 3 independently of one another preferably represent hydrogen, halogen, CI-C 6 alkyl, C-C 6 -alkoxy, C 1
-C
4 -haloalkyl or C-C 4 -haloalkoxy, CDC preferably represents one of the groups o 0 A A BB B (1), B (2), N G 0 G 20 D 0 -11 0 0 A A. N B (3), (4), S G N G O D O 0 0 A A B (5), B G (6), Q 11: G O 4 1X 6
Q
2 0 Q Q 6 A preferably represents hydrogen or in each case optionally halogen-substituted
C
1
-C
12 -alkyl, C 3 -C8-alkenyl, C 1
-C
1 o-alkoxy-C-C 8 -alkyl, C-Cio-alkylthio-C-C 6 -alkyl, 5 optionally halogen-, C-C 6 -alkyl- or Cl-C 6 -alkoxy-substituted C 3 -Cs-cycloalkyl in which optionally one or two not directly adjacent ring members are replaced by oxygen and/or sulphur or represents in each case optionally halogen-, C-C 6 -alkyl-,
C
1
-C
6 -haloalkyl-, C-C 6 -alkoxy-, C 1
-C
6 -haloalkoxy-, cyano- or nitro-substituted phenyl or phenyl-Ci-C 6 -alkyl, 10 B preferably represents hydrogen, C-C 12 -alkyl or CI-C 8 -alkoxy-C 1
-C
6 -alkyl, or A, B and the carbon atom to which they are attached preferably represent saturated
C
3 -CIo-cycloalkyl or unsaturated C 5
-C
1 o-cycloalkyl in which optionally one ring member is replaced by oxygen or sulphur and which are optionally mono- or disubstituted by C-C 8 -alkyl, C 3 -Clo-cycloalkyl, C 1
-C
8 -haloalkyl, CI-C 8 -alkoxy, 15 C-C 8 -alkylthio, halogen or phenyl, or A, B and the carbon atom to which they are attached preferably represent C 5
-C
6 cycloalkyl which is substituted by an alkylenediyl group which is optionally substituted by C 1
-C
4 -alkyl and which optionally contains one or two not directly adjacent oxygen and/or sulphur atoms, or by an alkylenedioxyl group or by an 20 alkylenedithioyl group which, together with the carbon atom to which it is attached, forms a further five- to eight-membered ring, or A, B and the carbon atom to which they are attached preferably represent C 3 -C8 cycloalkyl or C 5
-C
8 -cycloalkenyl in which two substituents together with the carbon atoms to which they are attached represent in each case optionally C-C 6 -alkyl-, 25 C-C 6 -alkoxy- or halogen-substituted C 2
-C
6 -alkanediyl, C 2
-C
6 -alkenediyl or C4-C6- - 12 alkanedienediyl in which optionally one methylene group is replaced by oxygen or sulphur, D preferably represents hydrogen, represents in each case optionally halogen substituted CI-C 12 -alkyl, C 3 -Cs-alkenyl, C 3
-C
8 -alkynyl, CI-CIo-alkoxy-C 2
-C
8 -alkyl, 5 optionally halogen-, CI-C 4 -alkyl-, CI-C 4 -alkoxy- or C-C 4 -haloalkyl-substituted
C
3
-C
8 -cycloalkyl in which optionally one ring member is replaced by oxygen or sulphur or in each case optionally halogen-, C 1
-C
6 -alkyl-, Cl-C 6 -haloalkyl-, Ci-C 6 alkoxy-, Cl-C 6 -haloalkoxy-, cyano- or nitro-substituted phenyl or phenyl-Ci-C 6 alkyl, 10 A and D together preferably represent in each case optionally substituted C 3
-C
6 -alkanediyl or C 3
-C
6 -alkenediyl in which optionally one methylene group is replaced by a carbonyl group, oxygen or sulphur suitable substituents being in each case: halogen, hydroxyl, mercapto or in each case optionally halogen-substituted CI-CIO 15 alkyl or C-C 6 -alkoxy, or a further C 3
-C
6 -alkanediyl grouping, C 3
-C
6 -alkenediyl grouping or a butadienyl grouping which is optionally substituted by CI-C 6 -alkyl or in which optionally two adjacent substituents together with the carbon atoms to which they are attached form a further saturated or unsaturated cycle having 5 or 6 ring atoms (in the case of the compound of the formula (I-), A and D together with 20 the atoms to which they are attached then preferably represent, for example, the groups AD-I to AD-10 mentioned below) which may contain oxygen or sulphur, A and Q 1 together preferably represent C 3
-C
6 -alkanediyl or C 4
-C
6 -alkenediyl, each of which is optionally mono- or disubstituted by identical or different substituents from the group consisting of halogen, of C 1 -CIo-alkyl, CI-C 6 -alkoxy, C 1
-C
6 -alkylthio, C 3
-C
7 25 cycloalkyl, each of which is optionally mono- to trisubstituted by identical or different halogen, and of benzyloxy and phenyl, each of which is optionally mono to trisubstituted by identical or different substituents from the group consisting of halogen, CI-C 6 -alkyl and CI-C 6 -alkoxy, which C 3
-C
6 -alkanediyl or C 4
-C
6 -alkenediyl is furthermore optionally bridged by a CI-Cr-alkanediyl group or by an oxygen atom, or 30 Q' preferably represents hydrogen or CI-C 4 -alkyl,
Q
2 , Q 4 , Q 5 and Q 6 independently of one another preferably represent hydrogen or CI-C4- - 13 alkyl,
Q
3 preferably represents hydrogen, C 1
-C
6 -alkyl, Ci-C 6 -alkoxy-Ci-C 2 -alkyl, C 1
-C
6 alkylthio-C-C 2 -alkyl, optionally halogen-, Cl-C 4 -alkyl- or C-C 4 -alkoxy-substituted
C
3
-C
8 -cycloalkyl in which optionally one methylene group is replaced by oxygen or 5 sulphur or represents optionally halogen-, C 1
-C
4 -alkyl-, Ci-C 4 -alkoxy-, CI-C 2 haloalkyl-, Ci-C 2 -haloalkoxy-, cyano- or nitro-substituted phenyl, or
Q
3 and Q 4 together with the carbon atom to which they are attached preferably represent an optionally Ci-C 4 -alkyl-, Ci-C 4 -alkoxy- or C-C 2 -haloalkyl-substituted C 3
-C
7 -ring in which optionally one ring member is replaced by oxygen or sulphur, 10 G preferably represents chlorine, bromine or nitro. In the radical definitions mentioned as being preferred, halogen represents fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine. W and Z independently of one another particularly preferably represent hydrogen, chlorine, bromine, Ci-C 3 -alkyl or Ci-C 3 -alkoxy, 15 X particularly preferably represents chlorine, bromine, Ci-C 4 -alkyl, C 1
-C
4 -alkoxy, Cl-C 3 -haloalkyl, Cl-C 3 -haloalkoxy or cyano, Y particularly preferably represents hydrogen, chlorine, bromine, CI-C 2 -alkyl, trifluoromethyl or represents the radical V2 20 V 1 particularly preferably represents hydrogen, fluorine, chlorine, bromine, C 1
-C
6 -alkyl, Cl-C 4 -alkoxy, Ci-Crhaloalkyl, Ci-C 2 -haloalkoxy, nitro or cyano,
V
2 particularly preferably represents hydrogen, fluorine, chlorine, bromine, Ci-C 4 -alkyl, Cl-C 4 -alkoxy, Ci-C 2 -haloalkyl or C-C 2 -haloalkoxy, CDC particularly preferably represents one of the groups - 14 o 0 A A B (1), B (2) /N G 0 G (2 D o A 0 A N B (3), I (4), S G DN G 0 0 A A B (5), B G (6), Q 2 O 5 Q 6 A particularly preferably represents hydrogen, represents C-C 6 -alkyl, C 1
-C
4 -alkoxy 5 C-C 2 -alkyl, each of which is optionally mono- to trisubstituted by fluorine or chlorine, or represents C 3
-C
7 -cycloalkyl which is optionally mono- or disubstituted by fluorine, chlorine, C-C 2 -alkyl or C-C 2 -alkoxy, B particularly preferably represents hydrogen or C-C 6 -alkyl, or A, B and the carbon atom to which they are attached particularly preferably represent 10 saturated C 3
-C
7 -cycloalkyl in which optionally one ring member is replaced by oxygen or sulphur and which is optionally monosubstituted by C 1
-C
4 -alkyl, C-C 2 haloalkyl or CI-C 4 -alkoxy, with the proviso that Q 3 then particularly preferably represents hydrogen or methyl, or A, B and the carbon atom to which they are attached particularly preferably represent 15 C 5
-C
6 -cycloalkyl which is substituted by an alkylenediyl group which optionally contains one or two not directly adjacent oxygen or sulphur atoms and which is optionally substituted by methyl or ethyl, or by an alkylenedioxyl group, which, together with the carbon atom to which it is attached, forms a further five- or six membered ring, with the proviso that Q 3 then particularly preferably represents 20 hydrogen or methyl, or A, B and the carbon atom to which they are attached particularly preferably represent - 15 C 3
-C
6 -cycloalkyl or C 5
-C
6 -cycloalkenyl in which two substituents together with the carbon atoms to which they are attached represent C 2
-C
4 -alkanediyl, C 2
-C
4 alkenediyl, where optionally one methylene group is replaced by oxygen, or butadienediyl, each of which is optionally monosubstituted by methyl or methoxy, 5 with the proviso that Q 3 then particularly preferably represents hydrogen or methyl, D particularly preferably represents hydrogen, represents CI-C 6 -alkyl, C 3
-C
6 -alkenyl, Ci-C 4 -alkoxy-C 2
-C
3 -alkyl, each of which is optionally mono- to trisubstituted by fluorine or chlorine, represents C 3
-C
7 -cycloalkyl which is optionally monosubstituted by CI-C 2 -alkyl, CI-C 2 -alkoxy or trifluoromethyl and in which 10 optionally one methylene group is replaced by oxygen or sulphur or (but not in the case of the compounds of the formula (I-1)) represents phenyl, pyridyl or benzyl, each of which is optionally mono- or disubstituted by fluorine, chlorine, bromine, CI-C4-alkyl, C 1
-C
2 -haloalkyl, C-C 4 -alkoxy or Cl-C 2 -haloalkoxy, or A and D together particularly preferably represent optionally substituted C 3
-C
5 -alkanediyl in 15 which one methylene group may be replaced by oxygen or sulphur, possible substituents being C-C 2 -alkyl, or A and D (in the case of the compounds of the formula (1-1)) together with the atoms to which they are attached particularly preferably represent one of the groups AD-i to AD-10: 20 N N N AD-I AD-2 AD-3 NA 5N AD-4 AD-5 AD-6 -16 N N N AD-7 AD-8 AD-9 AD-10 A and Q' together particularly preferably represent C 3
-C
4 -alkanediyl or C 3
-C
4 -alkenediyl, each of which is optionally mono- or disubstituted by identical or different substituents from the group consisting of CI-C 2 -alkyl and CI-C 2 -alkoxy, or 5 Q' particularly preferably represents hydrogen,
Q
2 particularly preferably represents hydrogen,
Q
4 , Q 5 and Q 6 independently of one another particularly preferably represent hydrogen or
CI-C
2 -alkyl, Q3 particularly preferably represents hydrogen, CI-C 4 -alkyl, Ci-C 4 -alkoxy-Ci-C 2 -alkyl, 10 CI-C 4 -alkylthio-CI-C 2 -alkyl or optionally methyl- or methoxy-substituted C 3
-C
6 cycloalkyl in which optionally one methylene group is replaced by oxygen or sulphur, or
Q
3 and Q 4 together with the carbon to which they are attached particularly preferably represent a saturated C 5
-C
6 -ring which is optionally mono- or disubstituted by CI-C 4 15 alkyl or CI-C 4 -alkoxy and in which optionally one ring member is replaced by oxygen or sulphur, with the proviso that A then particularly preferably represents hydrogen or methyl, G particularly preferably represents chlorine or nitro.
-17 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, 5 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 radical V 10 V, very particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, tert-butyl, methoxy, trifluoromethyl or trifluoromethoxy,
V
2 very particularly preferably represents hydrogen, fluorine, chlorine, methyl, methoxy or trifluoromethyl, CDC very particularly preferably represents one of the groups 0 0 A A B (1), B (2), N G 0 G 15 D 0 0 A. A N B (3,N(4), S G D G 0 0 0 0 A A B G B (5), Q o (6), 2 Q 6 Q 0 - 18 A very particularly preferably represents hydrogen, represents C-C 4 -alkyl or CrC2 alkoxy-Ci-C 2 -alkyl, each of which is optionally mono- to trisubstituted by fluorine, or represents C 3
-C
6 -cycloalkyl which is optionally monosubstituted by fluorine, methyl or methoxy, 5 B very particularly preferably represents hydrogen, methyl or ethyl, or A, B and the carbon atom to which they are attached very particularly preferably represent saturated C 5
-C
6 -cycloalkyl in which optionally one ring member is replaced by oxygen and which is optionally monosubstituted by methyl, trifluoromethyl, methoxy, ethoxy, propoxy, butoxy or isobutoxy, with the proviso 10 that Q 3 then very particularly preferably represents hydrogen, or A, B and the carbon atom to which they are attached very particularly preferably represent Cs-C 6 -cycloalkyl which is substituted by an alkylenedioxyl group which contains two not directly adjacent oxygen atoms, with the proviso that Q 3 then very particularly preferably represents hydrogen, 15 D very particularly preferably represents hydrogen, represents CI-C 4 -alkyl, C 3
-C
4 alkenyl, Cl-C 2 -alkoxy-C 2
-C
3 -alkyl or C 3
-C
6 -cycloalkyl in which optionally one methylene group is replaced by oxygen or sulphur, each of which radicals is optionally mono- to trisubstituted by fluorine, or (but not in the case of the compounds of the formula (I-1)) represents phenyl or pyridyl, each of which is 20 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 3
-C
5 alkanediyl in which optionally one carbon atom is replaced by oxygen or sulphur 25 and which is optionally mono- or disubstituted by methyl, or A and D (in the case of the compounds of the formula (I-1)) together with the atoms to which they are attached very particularly preferably represent the group:
N
-19 AD-i A and Q' together very particularly preferably represent C 3
-C
4 -alkanediyl which is optionally mono- or disubstituted by methyl or methoxy or Q1 very particularly preferably represents hydrogen, 5 Q 2 very particularly preferably represents hydrogen,
Q
4 , Q 5 and Q 6 independently of one another very particularly preferably represent hydrogen or methyl, Q3 very particularly preferably represents hydrogen, methyl, ethyl or C 3
-C
6 -cycloalkyl, or 10 Q 3 and Q 4 together with the carbon to which they are attached very particularly preferably represent a saturated CS-C 6 -ring which is optionally monosubstituted by methyl or methoxy and in which optionally one ring member is replaced by oxygen or sulphur, with the proviso that A then very particularly preferably represents hydrogen, G very particularly preferably represents chlorine or nitro, 15 W especially preferably represents hydrogen, chlorine, bromine, methyl, ethyl, methoxy or ethoxy, X especially preferably represents chlorine, bromine, methyl, ethyl, propyl, methoxy, ethoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy or cyano, Y especially preferably represents hydrogen, chlorine, bromine, methyl, 20 trifluoromethyl or represents the radical V V 23 VI especially preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, tert-butyl, methoxy, trifluoromethyl or trifluoromethoxy,
V
2 especially preferably represents hydrogen, fluorine, chlorine, methyl, methoxy or 25 trifluoromethyl, - 20 Z especially preferably represents hydrogen, methyl, chlorine or bromine, CDC especially preferably represents one of the groups 0 0 A A B (1), B (2), N/ G 0 G D 0 O A especially preferably represents hydrogen, represents CI-C 4 -alkyl or CI-C 2 -alkoxy 5 CI-C 2 -alkyl, each of which is optionally mono- to trisubstituted by fluorine, or represents C 3
-C
6 -cycloalkyl which is optionally monosubstituted by fluorine, methyl or methoxy, B especially preferably represents hydrogen, methyl or ethyl, or A, B and the carbon atom to which they are attached especially preferably represent 10 saturated C 5
-C
6 -cycloalkyl in which optionally one ring member is replaced by oxygen and which is optionally monosubstituted by methyl, trifluoromethyl, methoxy, ethoxy, propoxy, butoxy or isobutoxy, D especially preferably represents hydrogen, G especially preferably represents chlorine. 15 The general or preferred radical definitions or illustrations given above can be combined with one another as desired, i.e. including combinations between the respective ranges and preferred ranges. Preference according to the invention is given to the use of the compounds of the formula (I) which contain a combination of the meanings given above as being preferred (preferable). 20 Particular preference according to the invention is given to the use of the compounds of the formula (I) which contain a combination of the meanings given above as being particularly preferred. Very particular preference according to the invention is given to the use of the compounds of the formula (I) which contain a combination of the meanings given above as being very 25 particularly preferred.
-21 Special preference according to the invention is given to the use of the compounds of the formula (I) which contain a combination of the meanings given above as being especially preferred. Saturated or unsaturated hydrocarbon radicals, such as alkyl, alkylenediyl or alkenyl, can in 5 each case be straight-chain or branched as far as this is possible, including in combination with heteroatoms, such as, for example, in alkoxy. Unless indicated otherwise, optionally substituted radicals can be mono- or polysubstituted, where in the case of polysubstitution the substituents can be identical or different. In addition to the compounds mentioned in the examples, the following compounds of the 10 formula (I-1) may be specifically mentioned: O X A y B N N/ Cl - z D oW Table 1: W=CH 3 , X CH 3 ,Y=4-CH 3 ,Z H. A B D
CH
3
CH
3 H
C
2
H
5
CH
3 H
C
3
H
7
CH
3 H i-C 3
H
7
CH
3 H
CH
3 H
-(CH
2
)
4 H -(CH2)s- H -(CH2)2-0-(CH2)2- H -CH2-0-(CH2)3-H
-CH
2
-CHCH
3
-(CH
2
)
3 - H
-(CH
2
)
2
-CHCH
3
-(CH
2
)
2 - H - 22 A B D
-(CH
2
)
2
-CHOCH
3
-(CH
2
)
2 - H
-(CH
2
)
2
-CHOC
2
H
5
-(CH
2
)
2 - H -(CH2)2-C(CH3)2-(CH2)2- H Table 2: A, B and D as stated in Table I
W=CH
3 ; X=CH 3 ; Y=4-Cl;Z=H; Table 3: A, B and D as stated in Table 1 5 W = CH 3 ; X = CH 3 ; Y = 4-Br; Z H; Table 4: A, B and D as stated in Table I W = C 2
H
5 ; X = CH 3 ; Y =4-Cl; Z= H; Table 5: A, B and D as stated in Table I W = C 2 Hs; X = CH 3 ; Y = 4-Br; Z= H; 10 Table 6: A, B and D as stated in Table I W = C 2
H
5 ; X = C 2
H
5 ; Y = 4-Cl; Z = H; Table 7: A, B and D as stated in Table 1 W = C 2
H
5 ; X = C 2
H
5 ; Y = 4-Br; Z = H; Table 8: A, B and D as stated in Table 1 15 W=CH 3 ; X=Cl; Y=4-Cl; Z=H; Table 9: A, B and D as stated in Table 1
W=CH
3 ; X= Br; Y=4-Br; Z=H; Table 10: A, B and D as stated in Table 1 W = CH 3 ; X = Cl; Y = 4-Br; Z = H; -23 Table 11: A, B and D as stated in Table I W = CH 3 ; X = Br; Y = 4-Cl; Z = H; Table 12: A, B and D as stated in Table I W = C 2 Hs; X = Cl; Y = 4-Cl; Z = H; 5 Table 13: A, B and D as stated in Table I W = C 2
H
5 ; X = Br; Y = 4-Br; Z = H; Table 14: A, B and D as stated in Table 1 W = C 2
H
5 ; X = Cl; Y = 4-Br; Z = H; Table 15: A, B and D as stated in Table 1 10 W = C 2 H; X = Br; Y = 4-Cl; Z = H; Table 16: A, B and D as stated in Table 1 W = H; X = CH 3 ; Y = H; Z = H; Table 17: A, B and D as stated in Table I W=H;X= Cl;Y=H;Z=H; 15 Table 18: A, B and D as stated in Table I W = H; X = Br; Y = H; Z = H; Table 19: A, B and D as stated in Table I W=H; X= CH 3 ;Y=4-Cl;Z=H; Table 20: A, B and D as stated in Table 1 20 W=H;X=Cl;Y=4-CH 3 ;Z=H; Table 21: A, B and D as stated in Table I W = H; X = CH 3 ; Y = 4-CH 3 ; Z =H; - 24 Table 22: A, B and D as stated in Table I W = H; X = Cl; Y = 4-Cl; Z = H; Table 23: A, B and D as stated in Table I W = H; X = Cl; Y = 4-Br; Z = H; 5 Table 24: A, B and D as stated in Table I
W=CH
3 ; X = Cl; Y = 4-CH 3 ; Z = H; Table 25: A, B and D as stated in Table I
W=CH
3 ; X = Br; Y = 4-CH 3 ; Z = H; Table 26: A, B and D as stated in Table I 10 W=C 2 H; X = Cl; Y = 4-CH 3 ; Z = H; Table 27: A, B and D as stated in Table 1
W=C
2 H; X = Br; Y = 4-CH 3 ; Z = H; Table 28: A, B and D as stated in Table I W = C,H 5 ; X = CH 3 ; Y = 4-CH 3 ; Z = H; 15 Table 29: A, B and D as stated in Table I W = C 2
H
5 ; X = C 2
H
5 ; Y = 4-CH 3 ; Z = H; Table 30: A, B and D as stated in Table I
W=H;X=CH
3 ; Y = 4-CH 3 ; Z = 5-CH- 3 . Table 31: A, B and D as stated in Table 1 20 W=H;X=CH 3 ; Y = 4-Cl; Z = 5-CH 3 . Table 32: A, B and D as stated in Table I W = H; X = Br; Y = 4-CH 3 ; Z = 5-CH 3
.
- 25 Table 33: A, B and D as stated in Table 1 W = H; X = Cl; Y = 4-Cl; Z = 5-CH 3 . Table 34: A, B and D as stated in Table I W = H; X = CH 3 ; Y = 4-Br; Z = 5-CH 3 . 5 Table 35: A, B and D as stated in Table I W = H; X = Cl; Y = 4-CH 3 ; Z = 5-Cl. Table 36: A, B and D as stated in Table I W=H; X= CH 3 ;Y=H;Z=5-CH 3 . Table 37: A, B and D as stated in Table 1 10 W = H; X = Cl; Y = H; Z = 5-CH 3 . Table 38: A, B and D as stated in Table I W = H; X = Br; Y = H; Z = 5-CH 3 . Table 39: A, B and D as stated in Table I W = CH 3 ; X = CH 3 ; Y = 4-CH 3 ; Z = 3-CH 3 . 15 Table 40: A, B and D as stated in Table 1 W = CH 3 ; X = CH 3 ; Y = 4-CH 3 ; Z = 3-Cl. Table 41: A, B and D as stated in Table I W = CH 3 ; X = CH- 3 ; Y = 4-CH 3 ; Z = 3-Br. Table 42: A, B and D as stated in Table 1 20 W=CH 3
;X=CH
3 ;Y=H;Z=3-Cl. Table 43: A, B and D as stated in Table 1 W = CH 3 ; X = CH 3 ; Y = H; Z = 3-Br. The compounds of the formula (f) are known in principle from the laid-open publications cited 25 at the outset, or they can be prepared by the processes described therein. Preferred meanings of the groups listed above in connection with the crop plant compatibility improving compounds ("herbicide safeners") of the formulae (la), (Hb), (c), (Ild) and (He) - 26 are defined below. m preferably represents the numbers 0, 1, 2, 3 or 4. A preferably represents one of the divalent heterocyclic groupings shown below NN N N NCH 2 )
R
1 5 / R 1 3 0-N
OR
14
R
13
R
13 0 5 n preferably represents the numbers 0, 1, 2, 3 or 4. A2 preferably represents in each case optionally methyl-, ethyl-, methoxycarbonyl- or ethoxycarbonyl- or allyloxycarbonyl-substituted methylene or ethylene. RE 8 preferably represents hydroxyl, mercapto, amino, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, 10 methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino.
R
9 preferably represents hydroxyl, mercapto, amino, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, 1-methylhexyloxy, allyloxy, I-allyloxymethylethoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i 15 propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino. R'o preferably represents in each case optionally fluorine-, chlorine- and/or bromine substituted methyl, ethyl, n- or i-propyl. R11 preferably represents hydrogen, in each case optionally fluorine- and/or chlorine substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, propenyl, butenyl, propynyl 20 or butynyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, dioxolanylmethyl, furyl, furylmethyl, thienyl, thiazolyl, piperidinyl, or optionally fluorine-, chlorine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-substituted phenyl. R2 preferably represents hydrogen, in each case optionally fluorine- and/or chlorine 25 substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, propenyl, butenyl, propynyl or butynyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, -27 dioxolanylmethyl, furyl, furylmethyl, thienyl, thiazolyl, piperidinyl, or optionally fluorine-, chlorine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-substituted phenyl, or together with R" represents one of the radicals -CH 2 -0-CH 2
-CH
2 - and
-CH
2
-CH
2 -0-CH 2
-CH
2 -, which are optionally substituted by methyl, ethyl, furyl, 5 phenyl, a fused-on benzene ring or by two substituents which together with the C atom to which they are attached form a 5- or 6-membered carbocycle.
R
13 preferably represents hydrogen, cyano, fluorine, chlorine, bromine, or represents in each case optionally fluorine-, chlorine- and/or bromine-substituted methyl, ethyl, n- or i-propyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or phenyl. 10 R" preferably represents hydrogen, optionally hydroxyl-, cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.
R
1 5 preferably represents hydrogen, cyano, fluorine, chlorine, bromine, or represents in each case optionally fluorine-, chlorine- and/or bromine-substituted methyl, ethyl, n- or 15 i-propyl, n-, i-, s- or t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or phenyl. X1 preferably represents nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i 20 propoxy, difluoromethoxy or trifluoromethoxy.
X
2 preferably represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy. 25 X 3 preferably represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy. t preferably represents the numbers 0, 1, 2, 3 or 4. 30 v preferably represents the numbers 0, 1, 2, 3 or 4.
-28 R16 preferably represents hydrogen, methyl, ethyl, n- or i-propyl.
R
7 preferably represents hydrogen, methyl, ethyl, n- or i-propyl.
R
1 8 preferably represents hydrogen, in each case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or 5 t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino, or in each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, 10 cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino or cyclohexylamino. R19 preferably represents hydrogen, in each case optionally cyano-, hydroxyl-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, 15 n-, i- or s-butyl, in each case optionally cyano-, fluorine-, chlorine- or bromine substituted propenyl, butenyl, propynyl or butynyl, or in each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
R
20 preferably represents hydrogen, represents in each case optionally cyano-, hydroxyl-, 20 fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, in each case optionally cyano-, fluorine-, chlorine- or bromine-substituted propenyl, butenyl, propynyl or butynyl, in each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, or optionally nitro-, cyano-, 25 fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy- or trifluoromethoxy-substituted phenyl, or together with R' 9 represents in each case optionally methyl- or ethyl-substituted butane-I,4-diyl (trimethylene), pentane-I,5 diyl, I -oxa-butane- 1,4-diyl or 3-oxa-pentane- 1,5-diyl. 30 X 4 preferably represents nitro, cyano, carboxyl, carbamoyl, formyl, sulphamoyl, hydroxyl, amino, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or - 29 trifluoromethoxy.
X
5 preferably represents nitro, cyano, carboxyl, carbamoyl, formyl, sulphamoyl, hydroxyl, amino, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or 5 trifluoromethoxy. Examples of compounds of the formula (Ia) which are very particularly preferred as herbicide safeners according to the invention are listed in the table below. Table: Examples of the compounds of the formula (IIa) ([ (Ila) -C A 11 R8 -30 Example (Positions) No. (X')m A R8 Ila-] (2) Cl, (4) Cl ,NN OCH 3 N
H
3 C
OCH
3 0 Ila-2 (2) Cl, (4) Cl N', N OCH 3
H
3 C
OC
2
H
5 0 Ua-3 (2) Cl, (4) Cl N OC 2
H
5
H
3 C
OCH
3 0 Ila-4 (2) Cl, (4) Cl N, OC 2
H
5
H
3 C
OC
2
H
5 0 Ha-5 (2) Cl N OCH 3 la-6 (2) Cl, (4) Cl N OCH 3 -31 Example (Positions) No. (X')m A' R 8 IIa-7 (2) F N OCH 3 Ila-8 (2) F N N OCH 3 N / CI Ila-9 (2) Cl, (4) Cl N OC2Hs N Cl3C Ila-10 (2) Cl, (4) CF 3 N OCH 3 -N Ila-l (2)C NN OCH 3 ~N' F lla-12 - OCH 5 /I, 0-N Ila-13 (2) Cl, (4) Cl , 'N N OC 2
H
5
H
3
C
-32 Example (Positions) No. (XI)m A' R 8 Ula-14 (2) Cl, (4) CI , N OC2HS1
C
3
H
7 -i Ha-15 (2) Cl, (4) Cl N OC 2
H
5
C
4
H
9 -t Ha-1 6 (2) Cl, (4) CI -- CH OC 2
H
5 O-N Ha-17 (2) Cl, (4) Cl OC 2
H
5 O-N Ila-18 - OH 0-N Examples of compounds of the formula (Hb) which are very particularly preferred as herbicide safeners according to the invention are listed in the table below. )(3 4 5 X 2 3 6 2 N 0 O A2.jR (b) - 33 Table Examples of compounds of the formula ([Ub) Example (Position) (Position) No. x2 x3 A2 R 9 Hb-l (5) - CH2 OH Cl Ub-2 (5) - CH 2
OCH
3 Cl Hb-3 (5) - CH 2
OC
2
H
5 Cl Ib-4 (5) - CH 2
OC
3
H
7 -n Cl Ilb-5 (5) - CH 2
OC
3
H
7 -i Cl Ub-6 (5) - CH 2
OC
4
H
9 -n Cl IIb-7 (5) - CH 2
OCH(CH
3
)C
5
H
1 -n Cl llb-8 (5) (2) CH 2 OH Cl F IHb-9 (5) (2) CH 2 OH Cl Cl Ilb-10 (5) - CH 2
OCH
2
CH=CH
2 Cl Ilb-1I (5) - CH 2
OC
4
H
9 -i Cl -34 Example (Position) (Position) No. x2 X 3
A
2
R
9 lb-12 (5) - CH2 CH 2 Il H2C H2C 0 H CH 3 IIb-13 (5) - CH 2
OCH
2
CH=CH
2 ClCH o o IIb-14 (5) - H25 OC 2 HS Cl 0 0 ClO Examples of the compounds of the formula (IHc) which are very particularly preferred as herbicide safeners according to the invention are listed in the table below. O R O NNR U (Hc)
RC
- 35 Table: Examples of the compounds of the formula (Ic) Example No. R'0 N(R", R 12 ) Hc-I CHC1 2
N(CH
2
CH=CH
2
)
2 Hc-2 CHC1 2 H3C CH N 0 Ilc-3 CHC1 2 HC CH N 0
CH
3 Hc-4 CHC12 N O [Ic-5 CHC1 2
H
3 C CH N 0 C 6
H
5 Hc-6 CHC1 2
CH
3 N 0 IJc-7 CHCl 2 HC CH N 0
O
-36 Examples of the compounds of the formula (lid) which are very particularly preferred as herbicide safeners according to the invention are listed in the table below. R 17 O N 181 1 (X )t
SO
2 (Ed) 0 5 Table Examples of the compounds of the formula (Ud) Example (Positions) (Positions) No. R R 7
R
18
(X
4 ), (X 5 )V Ud-I H H CH 3 (2) OCH 3 Ild-2 H H C 2 Hs (2) OCH 3 Id-3 H H C 3
H
7 -n (2) OCH 3 ld-4 H H C 3
H
7 -i (2) OCH 3 Ild-5 H H (2) OCH 3 Ild-6 H H CH 3 (2) OCH 3 (5)CH 3 Ud-7 H H C 2
H
5 (2) OCH 3 (5) CH 3 Hd-8 H H C 3
H
7 -n (2) OCH 3 (5) CH 3 -37 Example (Positions) (Positions) No. R 6
R
18
(X
4 ), (X,), Ild-9 H H C 3
H
7 -i (2) OCH 3 (5)CH 3 nd-I 0 H H (2) OCH 3 (5)CH 3 Ild-Il H H OCH 3 (2)OCH 3 (5)CH 3 H d-12 H H OC 2
H
5 (2) OCH 3 (5)CH 3 fld-13 H H OC 3
H
7 -i (2) OCH 3 (5) CH 3 Hd-14 H H SCH 3 (2) OCH 3 (5)CH 3 Hd-15 H H SC 2 Hs (2) OCH 3 (5)CH 3 Ild-16 H H SC 3
H
7 -i (2) OCH 3 (5)CH 3 Ild-17 H H NHCH 3 (2) OCH 3 (5)CH 3 Ild- 18 H H NHC 2 HS (2) OCH 3 (5) CH 3 -38 Example (Positions) (Positions) No. R16 R'1 R 1(X 4 ), (X 5 ), Ild-19 H H NHC 3
H
7 -i (2) OCH 3 (5)CH 3 Hd-20 H H NH (2)OCH 3 (5)CH 3 Ild-21 H H NH CH 3 (2) OCH 3 Ild-22 H H NHC 3
H
7 -i (2) OCH 3 Id-23 H H N(CH 3
)
2 (2) OCH 3 IHd-24 H H N(CH 3
)
2 (3) CH 3 (4) CH 3 Ild-25 H H CH 2 -0-CH 3 (2) OCH 3 Examples of the compounds of the formula (Ie) which are very particularly preferred as herbicide safeners according to the invention are listed in the table below. 19 (X), R ' N R16 20 1 (X1 RR/ SO 2 (IHe) 0 5 Table Examples of the compounds of the formula (Ile) Example (Positions) (Positions) No. R16 R 19
R
20 (X4), (X) Ile-] H H CH 3 (2) OCH 3
-
-39 Example (Positions) (Positions) No. R'1 R9 R 20
(X
4 ), ()" Ile-2 H H C 2
H
5 (2) OCH 3 He-3 H H C 3
H
7 -n (2) OCH 3 le-4 H H C 3
H
7 -i (2) OCH 3 Ile-5 H H (2) OCH 3 Ile-6 H CH 3
CH
3 (2) OCH 3 IIe-7 H H CH 3 (2) OCH 3 (5)CH 3 He-8 H H C 2
H
5 (2) OCH 3 (5) CH 3 fle-9 H H C 3
H
7 -n (2) OCH 3 (5) CH 3 Ile-10 H H C 3
H
7 -i (2) OCH 3 (5) CH 3 He-Il H H (2) OCH 3 (5) CH 3 le-1 2 H CH 3
CH
3 (2) OCH 3 (5)CH 3 Most preference is given as the crop plant compatibility-improving compound [component (b)] to cloquintocet-mexyl, fenchlorazole-ethyl, isoxadifen-ethyl, mefenpyr-diethyl, furilazole, - 40 fenclorim, cumyluron, dymron, dichlorimid, dimepiperate and the compounds Ile-5, and He- 1I, with cloquintocet-mexyl, mefenpyr-diethyl, isoxadifen-ethyl, furilazole, dichlormid, fenclorim and He-5 being particularly emphasized. Examples of the selectively herbicidal combinations according to the invention of in each case 5 one active compound of the formula (I) and in each case one of the safeners defined above are listed in the table below. Table Examples of combinations according to the invention Active compounds of the formula (I) Safener I-i cloquintocet-mexyl I-I fenchlorazole-ethyl I-I isoxadifen-ethyl I-i mefenpyr-diethyl I-1 furilazole I fenclorim 1-1 cumyluron I-I daimuron/dymron I-1 dichlormid 1-1 dimepiperate I-I He-l I-I He-5 1-2 cloquintocet-mexyl 1-2 fenchlorazole-ethyl 1-2 isoxadifen-ethyl 1-2 mefenpyr-diethyl 1-2 furilazole 1-2 fenclorim 1-2 cumyluron -41 Active compounds of the formula (I) Safener 1-2 daimuron/dymron 1-2 dichlormid 1-2 dimepiperate 1-2 Ie-] 1 1-2 1le-5 1-3 cloquintocet-mexyl 1-3 fenchlorazole-ethyl 1-3 isoxadifen-ethyl 1-3 mefenpyr-diethyl 1-3 furilazole 1-3 fenclorim 1-3 cumyluron 1-3 daimuron/dymron 1-3 dichlormid 1-3 dimepiperate 1-3 lle-5 1-3 fle-Il 1-4 cloquintocet-mexyl 1-4 fenchlorazole-ethyl 1-4 isoxadifen-ethyl 1-4 mefenpyr-diethyl 1-4 furilazole 1-4 fenclorim 1-4 cumyluron 1-4 daimuron/dymron 1-4 dichlormid - 42 Active compounds of the formula (1) Safener 1-4 dimepiperate 1-4 Ile-]l 1-4 Dle-5 I-5 cloquintocet-mexyl 1-5 fenchlorazole-ethyl 1-5 isoxadifen-ethyl 1-5 mefenpyr-diethyl 1-5 furilazole 1-5 fenclorim I-5 cumyluron 1-5 daimuron/dymron 1-5 dichlormid 1-5 dimepiperate 1-5 Ile-5 I-5 Ile-I I 1-6 cloquintocet-mexyl 1-6 fenchlorazole-ethyl 1-6 isoxadifen-ethyl 1-6 mefenpyr-diethyl 1-6 furilazole 1-6 fenclorim 1-6 cumyluron 1-6 daimuron/dymron 1-6 dichlormid 1-6 dimepiperate 1-6 fle-5 -43 Active compounds of the formula (I) Safener 1-6 le-i I The compounds of the general formula (Ha) to be used as safeners are known and/or can be prepared by processes known per se (cf. WO-A-91/07874, WO-A-95/07897). The compounds of the general formula (Hb) to be used as safeners are known and/or can be 5 prepared by processes known per se (cf. EP-A-191736). The compounds of the general formula (1ic) to be used as safeners are known and/or can be prepared by processes known per se (cf. DE-A-2218097, DE-A-2350547). The compounds of the general formula (Hd) to be used as safeners are known and/or can be prepared by processes known per se (cf. DE-A-l 9621522/US-A-6235680). 10 The compounds of the general formula (Ile) to be used as safeners are known and/or can be prepared by processes known per se (cf. WO-A-99/66795/US-A-6251827). Surprisingly, it has now been found that the above-defined active compound combinations of substituted aryl ketones of the general formula (I) and safeners (antidotes) of group (b) listed above, whilst being tolerated very well by useful plants, have good insecticidal and/or 15 acaricidal activity and can be used in various crops, in particular in cereal (especially barley), but also in millet, maize and rice, for the selective control of insects. Here, it has to be considered to be surprising that, from a large number of known safeners or antidotes which are capable of antagonizing the damaging effect of a herbicide on the crop plants, it is in particular the abovementioned compounds of group (b) which neutralize the 20 damaging effect of substituted cyclic dicarbonyl compounds of the formula (1) on the crop plants virtually completely without negatively affecting the insecticidal and/or acaricidal activity with respect to the weeds. Furthermore, it has to be considered to be completely surprising that compounds from group (b) listed above are not only capable of virtually completely neutralizing the damaging effect 25 of substituted cyclic dicarbonyl compounds of the formula (I) on the crop plants but in some cases even enhance the insecticidal and/or acaricidal activity of the cyclic dicarbonyl compounds of the formula (1), so that a synergistic effect can be observed.
- 44 Emphasis is given here to the particularly advantageous effect of the particularly and most preferred combination partners from group (b), in particular in respect of sparing cereal plants, such as, for example, wheat, barley and rye, but also millet, maize and rice, as crop plants. 5 The combinations of active compounds can generally be used, for example, for the following plants: Dicotyledonous crops of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, lpomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cuburbita, Helianthus. 10 Monocotyledonous crops of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus, Allium. However, the use of the combinations of active compounds is by no means limited to these genera but equally also extends to other plants. The advantageous effect of the combinations of active compounds is particularly strongly 15 pronounced at certain concentration ratios. However, the weight ratios of the active compounds in the combinations of active compounds can be varied within relatively wide ranges. In general, 0.001 to 1000 parts by weight, preferably 0.01 to 100 parts by weight, particularly preferably 0.05 to 10 parts by weight and most preferably 0.07 to 1.5 parts by weight of one of the crop plant compatibility-improving compounds (antidotes/safeners) 20 mentioned above under (b) are present per part by weight of active compound of the formula (I) or salts thereof. The active compounds or active compound combinations can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspoemulsion concentrates, natural and 25 synthetic materials impregnated with active compound and microencapsulations in polymeric materials. These formulations are produced 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 surface-active agents, that is, emulsifiers and/or dispersants and/or foam formers.
- 45 If the extender used is water, it is also possible to use for example organic solvents as auxiliary solvents. Suitable liquid solvents are mainly: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as 5 cyclohexane or paraffins, for example mineral oil fractions, mineral and vegetable oils, alcohols, such as butanol or 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 dimethyl sulphoxide, and water. Suitable solid carriers are: 10 for example ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates; suitable as solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, and synthetic granules of inorganic and organic meals, and granules of 15 organic material such as sawdust, coconut shells, maize cobs and tobacco stalks; suitable as emulsifiers and/or foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates and protein hydrolysates; suitable as dispersants are: for example lignosulphite waste liquors and 20 methylcellulose. 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 natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations. Other possible additives are mineral and vegetable oils. 25 It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc. The formulations in general comprise between 0.1 and 95% by weight of active compounds, 30 including the active compounds with a safening effect, preferably between 0.5 and 90%. The combinations of active compounds are generally applied in the form of ready-to-use formulations. However, the active compounds contained in the combinations of active - 46 compounds may also be applied in the form of individual formulations which are mixed upon use, that is, in the form of tank mixes. The combinations of active compounds, as such or in their formulations, may furthermore also be used as a mixture with other known herbicides, again with ready-to-use formulations or tank 5 mixes being possible. A mixture with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, attractants, steriliants, bactericides, bird repellents, growth substances, plant nutrients and soil conditioners is also possible. It may furthermore be advantageous for specific applications, in particular for the post-emergence method, to incorporate into the formulations plant-compatible mineral or vegetable oils (for example the 10 commercial product "Rako Binol") or ammonium salts, such as, for example, ammonium sulphate or ammonium thiocyanate, as further additives. The combinations of active compounds can be used as such, in the form of their formulations or the use forms which can be prepared from these formulations by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. Application is 15 effected in the customary manner, for example by watering, spraying, atomizing, dusting or broadcasting. The application rates of the combinations of active compound can be varied within a certain range; they depend inter alia on the weather and on the soil factors. In general, the application rates are between 0.005 and 5 kg per ha, preferably between 0.01 and 2 kg per ha, particularly 20 preferably between 0.05 and 1.0 kg per ha. The combinations of active compounds can be applied before and after emergence of the plants, i.e. by the pre-emergenece and the post-emergence method. Depending on their properties, the safeners to be used can be employed for pretreating the seed of the crop plant (seed dressing) or be incorporated into the seed furrows before sowing or, 25 together with the herbicide, be applied before or after emergence of the plants. The combinations of active compounds are suitable for controlling animal pests, preferably arthropods and nematodes, in particular insects and arachnids, encountered in agriculture, in animal healthcare, in forests, in the protection of stored products and in the protection of materials, and also in the hygiene sector. They are effective against normally sensitive and 30 resistant species and against all or individual stages of development. The abovementioned pests include: -47 From the order of the Isopoda, for example, Oniscus asellus, Armadillidium vulgare, Porcellio scaber. From the order of the Diplopoda, for example, Blaniulus guttulatus. From the order of the Chilopoda, for example, Geophilus carpophagus, Scutigera spp.. 5 From the order of the Symphyla, for example, Scutigerella immaculata. From the order of the Thysanura, for example, Lepisma saccharina. From the order of the Collembola, for example, Onychiurus armatus. From the order of the Orthoptera, for example, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp., Schistocerca gregaria. 10 From the order of the Blattaria, for example, Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica. From the order of the Dermaptera, for example, Forficula auricularia. From the order of the Isoptera, for example, Reticulitermes spp.. From the order of the Phthiraptera, for example, Pediculus humanus corporis, Haematopinus 15 spp., Linognathus spp., Trichodectes spp., Damalinia spp.. From the order of the Thysanoptera, for example, Hercinothrips femoralis, Thrips tabaci, Thrips palmi, Frankliniella occidentalis. From the order of the Heteroptera, for example, Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.. 20 From the order of the Homoptera, for example, Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp., Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium comi, Saissetia oleae, 25 Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp..
-48 From the order of the Lepidoptera, for example, Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella xylostella, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, 5 Heliothis spp., Mamestra brassicae, Panolis flammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana, Cnaphalocerus spp., Oulema oryzae. 10 From the order of the Coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, 15 Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica, Lissorhoptrus oryzophilus. From the order of the Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius 20 spp., Monomorium pharaonis, Vespa spp.. From the order of the Diptera, for example, Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, 25 Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa, Hylemyia spp., Liriomyza spp.. From the order of the Siphonaptera, for example, Xenopsylla cheopis, Ceratophyllus spp.. From the class of the arachnids, for example, Scorpio maurus, Latrodectus mactans, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta 30 oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Hemitarsonemus spp., Brevipalpus spp.
-49 The plant-parasitic nematodes include, for example, Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp., Bursaphelenchus spp. 5 When used as insecticides, the combinations of active compounds can furthermore be present, in their commercial formulations and in the use forms prepared from these formulations, as a mixture with synergists. Synergists are compounds which enhance the activity of the active compounds, without it being necessary for the added synergist to be active for its part. 10 The content of active compounds of the use forms prepared from the commercial formulations may vary within wide ranges. The concentration of active compounds of the use forms may be from 0.0000001 to 95% by weight of active compound and is preferably from 0.0001 to 1% by weight. Application is carried out in a customary manner adapted to the use forms. 15 According to the invention, it is possible to treat all plants and parts of plants. Plants are to be understood here as meaning all plants and plant populations such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, 20 including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeder's certificates. Parts of plants are to be understood as meaning all above-ground and below-ground parts and organs of plants, such as shoot, leaf, flower and root, examples which may be mentioned being leaves, needles, stems, trunks, flowers, fruit bodies, fruits and seeds and also roots, tubers and rhizomes. Parts of plants also include 25 harvested plants and vegetative and generative propagation material, for example seedlings, tubers, rhizomes, cuttings and seeds. The treatment of the plants and parts of plants according to the invention with the active compounds is carried out directly or by action on their environment, habitat or storage area according to customary treatment methods, for example by dipping, spraying, evaporating, 30 atomizing, broadcasting, brushing-on and, in the case of propagation material, in particular in the case of seeds, furthermore by one- or multi-layer coating.
- 50 As already mentioned above, it is possible to treat all plants and their parts according to the invention. In a preferred embodiment, wild plant species and plant varieties, or those obtained by conventional biological breeding methods, such as crossing or protoplast fusion, and parts thereof, are treated. In a further preferred embodiment, transgenic plants and plant 5 varieties obtained by genetic engineering, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated. The term "parts" or "parts of plants" or "plant parts" has been explained above. Particularly preferably, plants of the plant varieties which are in each case commercially available or in use are treated according to the invention. 10 Depending on the plant species or plant varieties, their location and growth conditions (soils, climate, vegetation period, diet), the treatment according to the invention may also result in superadditive ("synergistic") effects. Thus, for example, reduced application rates 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, better plant 15 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, higher harvest yields, better quality and/or a higher nutritional value of the harvested products, better storage stability and/or processability of the harvested products are possible which exceed the effects which were actually to be expected. 20 The transgenic plants or plant varieties (i.e. those obtained by genetic engineering) which are preferred and to be treated according to the invention include all plants which, in the genetic modification, received genetic material which imparts particularly advantageous useful traits to these plants. Examples of such traits are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt 25 content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, better quality and/or a higher nutritional value of the harvested products, better storage stability and/or processability of the harvested products. Further and particularly emphasized examples of such properties are a better defence of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, 30 bacteria and/or viruses, and also increased tolerance of the plants to certain herbicidally active compounds. Examples of transgenic plants which may be mentioned are the important crop plants, such as cereals (wheat, rice), maize, soya beans, potatoes, cotton, oilseed rape and also fruit plants (with the fruits apples, pears, citrus fruits and grapes), and particular emphasis is given to maize, soya beans, potatoes, cotton and oilseed rape. Traits that are -51 particularly emphasized are the increased defence of the plants against insects by toxins formed in the plants, in particular those formed by the genetic material from Bacillus thuringiensis (for example by the genes CryIA(a), CryLA(b), CryIA(c), CryIIA, CrylIlA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CryIF and also combinations thereof) (hereinbelow 5 referred to as "Bt plants"). Traits that are furthermore particularly emphasized are the increased tolerance of the plants to certain herbicidally active compounds, for example imidazolinones, sulphonylureas, glyphosate or phosphinotricin (for example the "PAT" gene). The genes which impart the desired traits in question can also be present in combination with one another in the transgenic plants. Examples of "Bt plants" which may 10 be mentioned are maize varieties, cotton varieties, soya bean varieties and potato varieties which are sold under the trade names YIELD GARD@ (for example maize, cotton, soya beans), KnockOut@ (for example maize), StarLink® (for example maize), Bollgard@ (cotton), Nucotn@ (cotton) and NewLeaf® (potato). Examples of herbicide-tolerant plants which may be mentioned are maize varieties, cotton varieties and soya bean varieties which 15 are sold under the trade names Roundup Ready@ (tolerance to glyphosate, for example maize, cotton, soya bean), Liberty Link@ (tolerance to phosphinotricin, for example oilseed rape), IMI@ (tolerance to imidazolinones) and STS@ (tolerance to sulphonylureas, for example maize). Herbicide-resistant plants (plants bred in a conventional manner for herbicide tolerance) which may be mentioned include the varieties sold under the name 20 Clearfield@ (for example maize). Of course, these statements also apply to plant varieties having these or still-to-be-developed genetic traits, which plants will be developed and/or marketed in the future. The plants listed can be treated according to the invention in a particularly advantageous manner with the active compound mixtures. The preferred ranges stated above for the 25 mixtures also apply to the treatment of these plants. Particular emphasis is given to the treatment of plants with the mixtures specifically mentioned in the present text. Use examples Preparation of the 20 WS formulation and subsequent seed dressing In an agate mortar, the amount of safener and the amount of active compound required to 30 prepare a 20 WS formulation are dissolved in acetone, and the appropriate amount of formulation without active compounds (which is actually used to prepare Gaucho 70 WS) is added. The mixture is allowed to dry until only a small amount of residual moisture can be detected. Using a spatula, the substance is carefully detached from the side of the mortar, and - 52 the substance is comminuted in the mortar until it has dried. An amount of the laboratory formulation thus prepared which is appropriate for the amount of seed to be dressed is filled into beakers of a size big enough so that, during dressing, they are at most one third filled with seed. A sufficient amount of water (depending on the properties of the seed surface) is then 5 added. The seed is then filled into these beakers containing formulation and water and dressed on a test tube shaker with the aid of a spatula or glass rod. Once the formulation is distributed on the seed as uniformly as possible, the seed is allowed to dry in a fume hood. Practice of the test in seed trays 3 1 trays made of plastic (20 x 20 x 5 cm) are filled with sandy loam. Using a punch, the soil is 10 firmed such that the deposition depth required for the crop in question is achieved. 20 seeds/ seed tray are placed at regular intervals with the aid of a pair of tweezers impressed into the soil using the abovementioned punch. The test containers are placed in a greenhouse and, using the punch, the surface is once again firmed gently. In addition to the test substances, an untreated control is tested, too. Per variant, there are at least 2 trays. The trays are watered and 15 covered with a film until the plants have emerged. After emergence, the trays are watered 2 times a day. Evaluation is carried out by counting the plants that have emerged and by assessing damage (in %) over an interval of 5 - 14 days after sowing in comparison to the untreated control. Results for the greenhouse trials with safener after seed dressing: - 53 Example 1-1-1 H O CH3 N O CI CI O CH3 known from WO 03/029213, Ex. No. 1-1-c-I I Table A Application rate Maize g of ai/kg of seed evaluation after 14 d plants that have emerged in % % damage Example 1-1-1 2 71 95 a) Example 1-1-1 2+1 100 60 + 11-e-5 H-e-5 1 100 0 b) Example I-1-1 2 + 1 96 80 + Isoxadifen-ethyl Isoxadifen-ethyl 1 96 0 5 Table B Application rate Summer barley g of ai/kg of seed evaluation after 14 d plants that have emerged % damage in % Example 1-1-1 2 0 100 Example I-1-1 2+1 69 0 + Mefenpyr-diethyl Mefenpyr-diethyl 1 75 0 - 54 Table C Application rate Winter barley g of ai/kg of seed evaluation after 14 d plants that have emerged in % damage Example I-1-1 2 0 100 Example 1-1-1 2 + 1 76 0 + Mefenpyr-diethyl Mefenpyr-diethyl 1 83 0 - 55 Method: Safener test after spraying Variant a) Solvent: 7 parts by weight of DMF Emulsifier: 2 parts by weight of alkylaryl polyglycol ether 5 To produce a suitable preparation of active compound, I 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 desired amount of safener (in the case of mefenpyr diethyl as WP 20) is mixed into the water used for dilution. Furthermore, 2 g of ai/l of rapeseed oil methyl ester 500 EW are added. Leaves of winter barley at the 2-leaf stage which are 10 infested by the bird cherry-oat aphid (Rhopalosiphum padi) are treated with the desired active compound and safener concentrations using a spray boom, the water application rate being 300 I/ha. Per variant, the test is carried out at least twice. Evaluation is carried out after 7 d and/or 14 d by assessing the plant damage in %, where both the treated plant and new growth and the kill of the grain aphids in % compared to the untreated control are evaluated. 100% 15 damage means that the plant has died, and 0% means no damage. 100% effect on the grain aphids means that all aphids have been killed; 0% means that none of the aphids have been killed. Variant b) In variant b), the active compound is applied as an SC formulation in the desired 20 concentrations as in variant a) in a mixture with mefenpyr-diethyl WP 20 and 2 g of ai/l rapeseed oil methyl ester 500 EW. Practice and evaluation is carried out as stated in variant a). Results for greenhouse trials with safener after spraying against Rhopalosiphum padi on winter barley Example 1-1-2 CH3 O3 HN Br H 3CO CI1 25 O CH3 known from WO 03/029 213, Ex. I-1-a-9 -56 Table D (Variant b) Application rate Kill (%) Damage (%) g of ai/ha 7d 14d 7d 14d Example I-1-2 40 100 70 40 60 Example 1-1 -2 40+100 98 86 10 10 + Mefenpyr-diethyl Mefenpyr-diethyl 200 0 0 0 0 Table E (Variant b) Application rate Kill (%) Damage to new g of ai/ha growth (%) 7d 14d 7d 14d Example 1-1-2 40 100 70 100 100 Example 1-1 -2 40+100 98 86 0 30 + Mefenpyr-diethyl Mefenpyr-diethyl 200 0 0 0 0 5 Table F (Variant b) Application rate Kill (%) Damage to new g of ai/ha growth (%) 7d 14d 7d 14d Example 1-1-2 8 73 33 100 70 Example 1-1-2 8 + 200 93 37 0 0 + Mefenpyr-diethyl Mefenpyr-diethyl 200 0 0 0 0 - 57 Table G (Variant a) Application rate Kill (%) Damage (%) g of ai/ha 7d 14d 7d 14d Example 1-1-2 40 100 78 40 50 Example I-1-2 40+50 100 88 0 10 + Mefenpyr-diethyl Mefenpyr-diethyl 200 0 0 0 0 Table H (Variant a) Application rate Kill (%) Damage to new g of ai/ha growth (%) 7d 14d 7d 14d Example 1-1-2 40 100 78 70 80 Example -1-2 40+50 100 88 30 30 + Mefenpyr-diethyl Mefenpyr-diethyl 200 0 0 0 0 - 58 Formula to calculate the kill rate of a combination of two active compounds The expected activity of a given combination of two active compounds can be calculated according to S.R. Colby, Weeds 1 (1967), 20-22 as follows: if 5 X is the kill rate when employing active compound A at an application rate of m g/ha or in a concentration of m ppm, Y is the kill rate when employing active compound B at an application rate of n g/ha or in a concentration of n ppm and E is the kill rate when using the active compounds A and B at application rates of m 10 and n g/ha or in a concentration of m and n ppm, then X-Y E=X+Y- 100 Here, the kill rate is determined in %. 0% means a kill rate which corresponds to that of the control, whereas a kill rate of 100% means that no infection is observed. 15 If the actual activity exceeds the calculated value, the activity of the combination is superadditive, i.e. a synergistic effect is present. In this case, the actually observed kill rate must exceed the value calculated using the above formula for the expected kill rate (E).
- 59 Examples of spray application Solvent: water Adjuvant: rapeseed oil methyl ester (0.1 % of a.i./l) To prepare a suitable application solution, 1 part by weight of formulation is mixed with the 5 appropriate amount of water and the adjuvant and the concentrate is diluted with water to the desired concentration. Example I Aphis gossypii test Cotton plants (Gossypium herbaceum) which are heavily infested by the cotton aphid (Aphis 10 gossypii) are sprayed to runoff point with the desired concentration of the application solution. Example J Myzus persicae test Bell pepper plants (Capsicum sativum) which are heavily infested by the green peach aphid 15 (Myzus persicae) are sprayed to runoff point with the desired concentration of the application solution. Example K Metopolophium dirhodum test Barley plants (Hordeum vulgare) which are heavily infested by a grain aphids 20 (Metopolophium dirhodum) are sprayed to runoff point with the desired concentration of the application solution. After the desired period of time, the kill in % is determined. 100% means that all aphids have been killed; 0% means that none of the aphids have been killed. The determined kill rates are entered in Colby's formula. 25 In this test, for example, the following active compound combination in accordance with the present application shows a synergistically enhanced activity compared to the active compounds applied individually: - 60 Table I Plant-damaging insects Aphis gossypii test Active compound/formulation Concentration Kill rate in ppm in % after 3d Ex. (1-1-2) 20 0 known Isoxadifen-ethyl WG50 100 0 known Ex. (1-1 -2) + Isoxadifen-ethyl (1:5) found* calc. ** according to the invention 20 + 100 35 0 Mefenpyr-diethyl WG15 100 0 known Ex. (1-1-2) + Mefenpyr-diethyl (1:5) found* calc. ** according to the invention 20 + 100 55 0 Ex. (Ile-5) 100 0 known Ex. (1-1 -2) + (Ex. Ile-5) found* calc. ** according to the invention 20 + 100 55 0 Cloquintocet-mexyl WP20 100 0 known Ex. (1-1-2) + Cloquintocet-mexyl (1:5) found* calc. ** according to the invention 20 + 100 55 0 Fenclorim a.i. 100 0 known Ex. (1-1-2) + Fenclorim (1:5) found* calc. ** according to the invention 20 + 100 30 0 Furilazole a.i. 100 0 known Ex. (1-1-2) + Furilazole (1:5) found* calc. ** according to the invention 20 + 100 65 0 * found = activity found ** calc. = activity calculated using Colby's formula -61 Table I-continued Plant-damaging insects Aphis gossypii test Active compound/formulation Concentration Kill rate in ppm in % after 7d Ex. (1-1-1) 20 20 known Isoxadifen-ethyl WG50 100 0 known Ex. (I-1-1) + Isoxadifen-ethyl (1:5) found* calc. ** according to the invention 20 + 100 65 20 Mefenpyr-diethyl WG15 100 0 known Ex. (I-1-1) + Mefenpyr-diethyl (1:5) found* caic. ** according to the invention 20 + 100 55 20 Ex. (IIe-5) 100 0 known Ex. (I-I- 1) + (Ex. IIe-5) found* calc. ** according to the invention 20 + 100 65 20 Cloquintocet-mexyl WP20 100 0 known Ex. (I-1-1) + Cloquintocet-mexyl (1:5) found* calc. ** according to the invention 20 + 100 75 20 Dichlormid a.i. 100 0 known Ex. (I-1-1) + Dichlormid (1:5) found* calc. ** according to the invention 20 + 100 55 20 Fenclorim a.i. 100 0 known Ex. (I-1-1) + Fenclorim (1:5) found* calc. ** according to the invention 20 + 100 60 20 * found = activity found ** calc. = activity calculated using Colby's formula - 62 Table J Plant-damaging insects Myzus persicae test Active compound/formulation Concentration Kill rate in ppm in % after 7 d Ex. (I-1-2) 20 25 known Isoxadifen-ethyl WG50 100 0 known Ex. (1-1-2) + Isoxadifen-ethyl (1:5) found* calc. ** according to the invention 20 + 100 85 25 Mefenpyr-diethyl WG 15 100 0 known Ex. (1-1-2) + Mefenpyr-diethyl (1:5) found* calc. ** according to the invention 20 + 100 45 25 Ex. (Ile-5) 100 0 known Ex. (1-1-2) + (Ex. Ile-5) found* calc. ** according to the invention 20 + 100 65 25 Cloquintocet-mexyl WP20 100 0 known Ex. (1-1-2) + Cloquintocet-mexyl (1:5) found* calc. ** according to the invention 20 + 100 65 25 Dichlormid a.i. 100 0 known Ex. (1-1-2) + Dichlormid (1:5) found* calc. ** according to the invention 20 + 100 45 25 Fenclorim a.i. 100 0 known Ex. (1-1-2) + Fenclorim (1:5) found* calc. ** according to the invention 20 + 100 70 25 Furilazole a.i. 100 0 known Ex. (1-1-2) + Furilazole (1:5) found* calc. ** according to the invention 20 + 100 85 25 * found activity found, ** calc. = activity calculated using Colby's formula - 63 Table K Plant-damaging insects Metopolophium dirhodum test Active compound/formulation Concentration Kill rate in ppm in % after 7 d Ex. (1-1-2) 20 45 known Isoxadifen-ethyl WG50 100 0 known Ex. (1-1-2) + Isoxadifen-ethyl (1:5) found* calc. ** according to the invention 20 + 100 65 45 Mefenpyrdiethyl WG15 100 0 known Ex. (1-1-2) + Mefenpyr-diethyl (1:5) found* calc. ** according to the invention 20 + 100 70 45 Ex. (IIe-5) 100 0 known Ex. (1-1 -2) + (Ex. Ile-5) found* calc. ** according to the invention 20 + 100 75 45 Cloquintocet-mexyl a.i. 100 0 known Ex. (1-1-2) + Cloquintocet-mexyl (1:5) found* calc. ** according to the invention 20 + 100 65 45 Furilazole a.i. 100 0 known Ex. (1-1-2) + Furilazole (1:5) found* calc. ** according to the invention 20 + 100 85 45 * found = activity found ** calc. = activity calculated using Colby's formula - 64 Example L Critical concentration test / soil insects - treatment of transgenic plants Test insect: Diabrotica balteata - larvae in soil Solvent: 7 parts by weight of acetone 5 Emulsifier: I part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, I part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration. The preparation of active compound is poured onto the soil. Here, the concentration of 10 active compound in the preparation is virtually irrelevant; only the amount by weight of active compound per volume unit of soil, which is stated in ppm (mg/I), matters. 0.25 1 pots are filled with the soil and allowed to stand at 20*C. Immediately after preparation, 5 pre-germinated maize corns of the cultivar YIELD GUARD (trade mark of Monsanto Comp., USA) are placed into each pot. After 2 days, the 15 corresponding test insects are placed into the treated soil. After a further 7 days, the efficacy of the active compound is determined by counting the maize plants that have emerged (I plant = 20% efficacy).
-65 Example M Heliothis virescens test - treatment of transgenic plants Solvent: 7 parts by weight of acetone Emulsifier: I part by weight of alkylaryl polyglycol ether 5 To produce a suitable preparation of active compound, I 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. Soya bean shoots (Glycine max) of the cultivar Roundup Ready (trade mark of Monsanto Comp., USA) are treated by being dipped into the preparation of active compound of the 10 desired concentration and are populated with the tobacco budworm Heliothis virescens while the leaves are still moist. After the desired period of time, the kill of the insects is determined.

Claims (4)

  1. 4-dichloroacetyl- 1 -oxa-4-azaspiro[4.5]decane (AD-67, MON-4660), I -dichloroacetyl-hexahydro-3,3,8a-trimethylpyrrolo[ 1,2-a]pyrimidin-6(2H) one (dicyclonon, BAS-145138), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H 15 1,4-benzoxazine (benoxacor), 1-methylhexyl 5-chloroquinolin-8-oxyacetate (cloquintocet-mexyl - cf. also related compounds in EP-A-86750, EP-A-94349, EP-A-191736, EP-A-492366),3-(2-chlorobenzyl)-1-(1-methyl I-phenylethyl)urea (cumyluron), ct-(cyanomethoximino)-phenylacetonitrile (cyometrinil), 2,4-dichlorophenoxyacetic acid (2,4-D), 4-(2,4-dichloro 20 phenoxy)butyric acid (2,4-DB), 1-(1-methyl-I-phenylethyl)-3-(4-methyl phenyl)urea (daimuron, dymron), 3,6-dichloro-2-methoxybenzoic acid (dicamba), S-I-methyl-i -phenylethyl piperidine- I -thiocarboxylate (dimepiperate), 2,2-dichloro-N-(2-oxo-2-(2-propenylamino)ethyl) N-(2-propenyl)acetamide (DKA-24), 2,2-dichloro-N,N-di-2-propenyl 25 acetamide (dichlormid), 4,6-dichloro-2-phenylpyrimidine (fenclorim), ethyl 1-(2,4-dichlorophenyl)-5-trichloromethyl- 1 H-I ,2,4-triazole-3-carboxylate (fenchlorazole-ethyl - cf. also related compounds in EP-A-174562 and EP-A-346620), phenylmethyl 2-chloro-4-trifluoromethylthiazole-5 carboxylate (flurazole), 4-chloro-N-(1,3-dioxolan-2-ylmethoxy)-a-tri 30 fluoroacetophenone oxime (fluxofenim), 3-dichloroacetyl-5-(2-furanyl)-2,2 dimethyloxazolidine (furilazole, MON-13900), ethyl 4,5-dihydro-5,5 diphenyl-3-isoxazolecarboxylate (isoxadifen-ethyl - cf. also related -69 compounds in WO-A-95/07897), 1-(ethoxycarbonyl)ethyl-3,6-dichloro-2 methoxybenzoate (lactidichlor), (4-chloro-o-tolyloxy)acetic acid (MCPA), 2-(4-chloro-o-tolyloxy)propionic acid (mecoprop), diethyl I-(2,4-dichloro phenyl)-4,5-dihydro-5-methyl- I H-pyrazole-3,5-dicarboxylate (mefenpyr 5 diethyl - cf. also related compounds in WO-A-91/07874), 2-dichloromethyl 2-methyl-1,3-dioxolane (MG-191), 2-propenyl-1-oxa-4-azaspiro[4.5]decane 4-carbodithioate (MG-838), 1,8-naphthalic anhydride, c-(1,3-dioxolan-2-yl methoximino)phenylacetonitrile (oxabetrinil), 2,2-dichloro-N-(1,3-dioxolan 2-ylmethyl)-N-(2-propenyl)acetamide (PPG-1292), 3-dichloroacetyl-2,2 10 dimethyloxazolidine (R-28725), 3-dichloroacetyl-2,2,5-trimethyloxazolidine (R-29148), 4-(4-chloro-o-tolyl)butyric acid, 4-(4-chlorophenoxy)-butyric acid, diphenylmethoxyacetic acid, methyl diphenylmethoxyacetate, ethyl diphenylmethoxyacetate, methyl I-(2-chlorophenyl)-5-phenyl-IH-pyrazole 3-carboxylate, ethyl 1-(2,4-dichlorophenyl)-5-methyl- I H-pyrazole-3 15 carboxylate, ethyl 1-(2,4-dichlorophenyl)-5-isopropyl- 1 H-pyrazole-3 carboxylate, ethyl 1-(2,4-dichlorophenyl)-5-(1,1 -dimethylethyl)- I H pyrazole-3 -carboxylate, ethyl I-(2,4-dichlorophenyl)-5-phenyl-lH-pyrazole 3-carboxylate (cf. also related compounds in EP-A-269806 and EP-A-333131), ethyl 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate, 20 ethyl 5-phenyl-2-isoxazoline-3 -carboxylate, ethyl 5-(4-fluorophenyl)-5 phenyl-2-isoxazoline-3-carboxylate (cf. also related compounds in WO-A-91/08202), 1,3-dimethylbut- I -yl 5-chloroquinolin-8-oxyacetate, 4-allyloxybutyl 5-chloroquinolin-8-oxyacetate, I -allyloxyprop-2-yl 5-chloro quinolin-8-oxyacetate, methyl 5-chloroquinoxalin-8-oxyacetate, ethyl 25 5-chloroquinolin-8-oxyacetate, allyl 5-chloroquinoxalin-8-oxyacetate, 2-oxoprop-1-yl 5-chloroquinolin-8-oxyacetate, diethyl 5-chloroquinolin-8 oxymalonate, diallyl 5-chloroquinoxalin-8-oxymalonate, diethyl 5 chloroquinolin-8-oxymalonate (cf. also related compounds in EP-A-582198), 4-carboxy-chroman-4-ylacetic acid (AC-304415, cf. 30 EP-A-613618), 4-chlorophenoxyacetic acid, 3,3'-dimethyl-4 methoxybenzophenone, I -bromo-4-chloromethylsulphonylbenzene, 1-[4-(N 2-methoxybenzoylsuiphamoyl)phenyl]-3-methylurea (alias N-(2 methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulphonamide), 1-[4-(N-2-methoxybenzoylsulphamoyl)-phenyl]-3,3-dimethylurea, 1-[4-(N 35 4,5-dimethylbenzoylsulphamoyl)phenyl]-3-methylurea, 1-[4-(N- - 70 naphthylsulphamoyl)phenyl]-3,3-dimethylurea, N-(2-methoxy-5 methylbenzoyl)-4-(cyclopropylaminocarbonyl)benzenesulphonamide, and/or one of the following compounds (defined by general formulae) of the general formula (Ila) 1X 0(Ia 5 A R(Ia or of the general formula (Ilb) X 3 X 2 N 0 (H1b) OA2 R(Ib or of the formula (I1c) 0 R 1 N(Hc) R 10 where m represents a number 0, 1, 2, 3, 4 or 5, A' represents one of the divalent heterocyclic groups outlined hereinbelow, N N N (CH R'N N NR 1 R ~~R N R O-N OR 14 R 1 R" 0 15 n represents a number 0, 1, 2, 3, 4 or 5, -71 A 2 represents alkanediyl having I or 2 carbon atoms which is optionally substituted by C 1 -C 4 -alkyl and/or Ci-C 4 -alkoxycarbonyl and/or Ci-C 4 alkenyloxy-carbonyl, R 8 represents hydroxyl, mercapto, amino, Ci-C 7 -alkoxy, CI-C 6 -alkenyloxy, CI-C 6 5 alkenyloxy-Ci-C 6 -alkoxy, C 1 -C 6 -alkylthio, C-C 6 -alkylamino or di-(CI-C 4 alkyl)amino, R 9 represents hydroxyl, mercapto, amino, CI-C 6 -alkoxy, CI-C 6 -alkylthio, CI-C 6 alkylamino or di-(CI-C 4 -alkyl)amino, R1 represents CI-C 4 -alkyl which is optionally substituted in each case by 10 fluorine, chlorine and/or bromine, R" represents hydrogen, or represents Cl-C 6 -alkyl, C 2 -C 6 -alkenyl or C 2 -C 6 alkynyl, C 1 -C 4 -alkoxy-Ci-C 4 -alkyl, dioxolanyl-Cl-C 4 -alkyl, furyl, furyl C,-C 4 -alkyl, thienyl, thiazolyl, piperidinyl, each of which is optionally substituted by fluorine, chlorine and/or bromine, or represents phenyl which 15 is optionally substituted by fluorine, chlorine and/or bromine or CI-C 4 -alkyl, R2 represents hydrogen, or represents CI-C 6 -alkyl, C 2 -C 6 -alkenyl or C 2 -C 6 alkynyl, C-C 4 -alkoxy-Cl-C 4 -alkyl, dioxolanyl-C-C 4 -alkyl, furyl, furyl CI-C 4 -alkyl, thienyl, thiazolyl, piperidinyl, each of which is optionally substituted by fluorine, chlorine and/or bromine, or represents phenyl which 20 is optionally substituted by fluorine, chlorine and/or bromine or CI-C 4 -alkyl, or R" and R 2 together represent C 3 -C 6 -alkanediyl or C 2 -Cs-oxaalkanediyl, each of which is optionally substituted by CI-C 4 -alkyl, phenyl, furyl, a fused benzene ring or by two substituents which, together with the C atom to which they are bonded, form a 5- or 6-membered carbocycle, 25 R 13 represents hydrogen, cyano, halogen, or represents Ci-C 4 -alkyl, C 3 -C 6 cycloalkyl or phenyl, each of which is optionally substituted by fluorine, chlorine and/or bromine, R 14 represents hydrogen, or represents CI-C 6 -alkyl, C 3 -C 6 -cycloalkyl or tri(CI-C 4 -alkyl)silyl, optionally substituted by hydroxyl, cyano, halogen or 30 C 1 -C 4 -alkoxy, -72 R'" represents hydrogen, cyano, halogen, or represents CI-C 4 -alkyl, C 3 -C 6 cycloalkyl or phenyl, each of which is optionally substituted by fluorine, chlorine and/or bromine, X 1 represents nitro, cyano, halogen, CI-C 4 -alkyl, C 1 -C 4 -haloalkyl, Ci-C 4 -alkoxy 5 or Cl-C 4 -haloalkoxy, x2 represents hydrogen, cyano, nitro, halogen, CI-C 4 -alkyl, C 1 -C 4 -haloalkyl, Ci-C 4 -alkoxy or C-C 4 -haloalkoxy, x3 represents hydrogen, cyano, nitro, halogen, Cl-C 4 -alkyl, CI-C 4 -haloalkyl, CI-C 4 -alkoxy or C 1 -C 4 -haloalkoxy, 10 and/or the following compounds (defined by general formulae) of the general formula (Ud) R 1 11 0 N (X,), IR 16 SO 2 (fld) O or of the general formula (He) 19 (X )X R N 1 20 |( 4 SO 2 (He) 0 15 where t represents a number 0, 1, 2, 3, 4 or 5, v represents a number 0, 1, 2, 3, 4 or 5, R' 6 represents hydrogen or CI-C 4 -alkyl, - 73 R" 7 represents hydrogen or CI-C 4 -alkyl, R 18 represents hydrogen, or represents CI-C 6 -alkyl, CI-C 6 -alkoxy, CI-C 6 alkylthio, CI-C 6 -alkylamino or di-(CI-C 4 -alkyl)amino, each of which is optionally substituted by cyano, halogen or C 1 -C 4 -alkoxy, or represents 5 C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyloxy, C 3 -C 6 -cycloalkylthio or C 3 -C 6 cycloalkylamino, each of which is optionally substituted by cyano, halogen or CI-C 4 -alkyl, R19 represents hydrogen, or represents CI-C 6 -alkyl which is optionally substituted by cyano, hydroxyl, halogen or CI-C 4 -alkoxy, or represents 10 C 3 -C 6 -alkenyl or C 3 -C 6 -alkynyl, each of which is optionally substituted by cyano or halogen, or represents C 3 -C 6 -cycloalkyl which is optionally substituted by cyano, halogen or CI-C 4 -alkyl, R 20 represents hydrogen, or represents CI-C 6 -alkyl which is optionally substituted by cyano, hydroxyl, halogen or CI-C 4 -alkoxy, or represents 15 C 3 -C 6 -alkenyl or C 3 -C 6 -alkynyl, each of which is optionally substituted by cyano or halogen, or represents C 3 -C 6 -cycloalkyl which is optionally substituted by cyano, halogen or Ci-C 4 -alkyl, or represents phenyl which is optionally substituted by nitro, cyano, halogen, Ci-C 4 -alkyl, CI-C 4 -haloalkyl, CI-C 4 -alkoxy or C 1 -C 4 -haloalkoxy, or together with R' 9 represents C 2 -C 6 20 alkanediyl or C 2 -C 5 -oxaalkanediyl, each of which is optionally substituted by CI-C 4 -alkyl, X 4 represents nitro, cyano, carboxyl, carbamoyl, formyl, sulphamoyl, hydroxyl, amino, halogen, CI-C 4 -alkyl, CI-C 4 -haloalkyl, CI-C 4 -alkoxy or CI-C4 haloalkoxy, and 25 X represents nitro, cyano, carboxyl, carbamoyl, formyl, sulphamoyl, hydroxyl, amino, halogen, CI-C 4 -alkyl, CI-C 4 -haloalkyl, Ci-C 4 -alkoxy or CI-C4 haloalkoxy, for controlling insects and/or arachnids. 2. Use of a composition according to Claim 1 for controlling insects and/or arachnids, 30 which composition comprises compounds of the formula (I) in which -74 W and Z independently of one another represent hydrogen, halogen, CI-C 6 -alkyl, CI-C 6 -haloalkyl or CI-C 6 -alkoxy, X represents halogen, CI-C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, CI-C 6 haloalkyl, CI-C 6 -alkoxy, C 3 -C 6 -alkenyloxy, Ci-C 6 -haloalkoxy, C 3 -C 6 5 haloalkenyloxy, nitro or cyano, Y represents hydrogen, halogen, CI-C 4 -alkyl, CI-C 2 -haloalkyl, CI-C 2 haloalkoxy, cyano or one of the radicals V V 2 V 2 ,' V31 V S V3 S v2 10 in which VI represents hydrogen, halogen, CI-C 1 2 -alkyl, CI-C 6 -alkoxy, CI-C 4 -haloalkyl, CI-C 4 -haloalkoxy, nitro or cyano, V 2 and V 3 independently of one another represent hydrogen, halogen, CI-C 6 -alkyl, C 1 -C 6 -alkoxy, CI-C 4 -haloalkyl or CI-C 4 -haloalkoxy, 1 5 CDC represents one of the groups o 0 A A B N(1), B (2) / G G D 0 o 0 A A, N B (3), (4), S G N G 0 D 0 -75 0 0 A A B G B (5), B() SGO (6), Q2 0 Q 5 Q A represents hydrogen or in each case optionally halogen-substituted CI-Ci 2 alkyl, C 3 -C 8 -alkenyl, C 1 -Cio-alkoxy-CI-C 8 -alkyl, CI-C 1 o-alkylthio-CI-C alkyl, optionally halogen-, CI-C 6 -alkyl- or Ci-C 6 -alkoxy-substituted C 3 -C 8 5 cycloalkyl in which optionally one or two not directly adjacent ring members are replaced by oxygen and/or sulphur or represents in each case optionally halogen-, CI-C 6 -alkyl-, C 1 -C 6 -haloalkyl-, C-C 6 -alkoxy-, Ci-C 6 haloalkoxy-, cyano- or nitro-substituted phenyl or phenyl-C 1 -C 6 -alkyl, B represents hydrogen, Ci-C 12 -alkyl or Ci-C 8 -alkoxy-CI-C 6 -alkyl, or 10 A, B and the carbon atom to which they are attached represent saturated C 3 -CIO cycloalkyl or unsaturated CS-Cio-cycloalkyl in which optionally one ring member is replaced by oxygen or sulphur and which are optionally mono- or disubstituted by CI-Cs-alkyl, C 3 -Clo-cycloalkyl, Ci-Cg-haloalkyl, CI-Cs alkoxy, C-C 8 -alkylthio, halogen or phenyl, or 15 A, B and the carbon atom to which they are attached represent C 5 -C 6 -cycloalkyl which is substituted by an alkylenediyl group which is optionally substituted by Ci-C 4 -alkyl and which optionally contains one or two not directly adjacent oxygen and/or sulphur atoms, or by an alkylenedioxyl group or by an alkylenedithioyl group which, together with the carbon atom to which it 20 is attached, forms a further five- to eight-membered ring, or A, B and the carbon atom to which they are attached represent C 3 -Cs-cycloalkyl or C 5 -C8-cycloalkenyl in which two substituents together with the carbon atoms to which they are attached represent in each case optionally CI-C 6 alkyl-, CI-C 6 -alkoxy- or halogen-substituted C 2 -C 6 -alkanediyl, C 2 -C 6 25 alkenediyl or C 4 -C 6 -alkanedienediyl in which optionally one methylene group is replaced by oxygen or sulphur, D represents hydrogen, represents in each case optionally halogen-substituted CI-C 12 -alkyl, C 3 -C-alkenyl, C 3 -C 8 -alkynyl, CI-Clo-alkoxy-C 2 -Cs-alkyl, -76 optionally halogen-, CI-C 4 -alkyl-, Ci-C 4 -alkoxy- or Cl-C 4 -haloalkyl substituted C 3 -C 8 -cycloalkyl in which optionally one ring member is replaced by oxygen or sulphur or in each case optionally halogen-, Ci-C 6 alkyl-, C-C 6 -haloalkyl-, Ci-C-alkoxy-, Ci-C-haloalkoxy-, cyano- or nitro 5 substituted phenyl or phenyl-Ci-C 6 -alkyl, A and D together represent in each case optionally substituted C 3 -C 6 -alkanediyl or C 3 -C 6 -alkenediyl in which optionally one methylene group is replaced by a carbonyl group, oxygen or sulphur, suitable substituents being in each case: 10 halogen, hydroxyl, mercapto or in each case optionally halogen-substituted CI-Cio-alkyl or CI-C 6 -alkoxy, or a further C 3 -C 6 -alkanediyl grouping, C 3 -C 6 alkenediyl grouping or a butadienyl grouping which is optionally substituted by CI-C 6 -alkyl or in which optionally two adjacent substituents together with the carbon atoms to which they are attached form a further saturated or 15 unsaturated cycle having 5 or 6 ring atoms (in the case of the compound of the formula (1-1), A and D together with the atoms to which they are attached then represent, for example, the groups AD-I to AD-10 mentioned below) which may contain oxygen or sulphur, A and Q 1 together represent C 3 -C 6 -alkanediyl or C 4 -C 6 -alkenediyl, each of which is 20 optionally mono- or disubstituted by identical or different substituents from the group consisting of halogen, of CI-CIO-alkyl, CI-C 6 -alkoxy, CI-C 6 alkylthio, C 3 -C 7 -cycloalkyl, each of which is optionally mono- to trisubstituted by identical or different halogen, and of benzyloxy and phenyl, each of which is optionally mono- to trisubstituted by identical or different 25 substituents from the group consisting of halogen, Ci-C 6 -alkyl and CI-C 6 alkoxy, which C 3 -C 6 -alkanediyl or C 4 -C 6 -alkenediyl is furthermore optionally bridged by a CI-C 2 -alkanediyl group or by an oxygen atom, or Q1 represents hydrogen or CI-C 4 -alkyl, Q1, Q 4 , Qs and Q 6 independently of one another represent hydrogen or Ci-C 4 -alkyl, 30 Q 3 represents hydrogen, CI-C 6 -alkyl, CI-C 6 -alkoxy-CI-C-alkyl, Cl-C 6 -alkylthio Ci-C 2 -alkyl, optionally halogen-, CI-C 4 -alkyl- or C-C 4 -alkoxy-substituted -77 C 3 -C 8 -cycloalkyl in which optionally one methylene group is replaced by oxygen or sulphur or represents optionally halogen-, CI-C 4 -alkyl-, C 1 -C 4 alkoxy-, C -C 2 -haloalkyl-, C 1 -C 2 -haloalkoxy-, cyano- or nitro-substituted phenyl, or 5 Q 3 and Q 4 together with the carbon atom to which they are attached represent an optionally CI-C 4 -alkyl-, CI-C 4 -alkoxy- or Cl-C 2 -haloalkyl-substituted C 3 -C 7 ring in which optionally one ring member is replaced by oxygen or sulphur, G represents chlorine, bromine or nitro. 3. Use of a composition according to Claim I for controlling insects and/or arachnids, 10 which composition comprises compounds of the formula (I) in which W and Z independently of one another represent hydrogen, chlorine, bromine, C 1 -C 3 -alkyl or Ci-C 3 -alkoxy, X represents chlorine, bromine, CI-C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 3 -haloalkyl, CI-C 3 -haloalkoxy or cyano, 15 Y represents hydrogen, chlorine, bromine, CI-C 2 -alkyl, trifluoromethyl or represents the radical vi V2V V' represents hydrogen, fluorine, chlorine, bromine, CI-C 6 -alkyl, CI-C 4 -alkoxy, CI-C 2 -haloalkyl, Ci-C 2 -haloalkoxy, nitro or cyano, 20 V 2 represents hydrogen, fluorine, chlorine, bromine, CI-C 4 -alkyl, CI-C 4 -alkoxy, CI-C 2 -haloalkyl or C-C 2 -haloalkoxy, CDC represents one of the groups 0 0 A A B (1), B (2) N 0 D G O 0 0 0 -78 o A O A N B (3), 1 (4), S G DN G 0 0 A A B G (6), Q 1 : G Q4 O Q2 0 aQ 5 Q A represents hydrogen, represents C-C 6 -alkyl, C-C 4 -alkoxy-C-C 2 -alkyl, each of which is optionally mono- to trisubstituted by fluorine or chlorine, or 5 represents C 3 -C 7 -cycloalkyl which is optionally mono- or disubstituted by fluorine, chlorine, C-C 2 -alkyl or C-C 2 -alkoxy, B represents hydrogen or C-C 6 -alkyl, or A, B and the carbon atom to which they are attached represent saturated C 3 -C 7 cycloalkyl in which optionally one ring member is replaced by oxygen or 10 sulphur and which is optionally monosubstituted by C 1 -C 4 -alkyl, C-C 2 haloalkyl or C-C 4 -alkoxy, with the proviso that Q 3 then represents hydrogen or methyl, or A, B and the carbon atom to which they are attached represent C 5 -C 6 -cycloalkyl which is substituted by an alkylenediyl group which optionally contains one 15 or two not directly adjacent oxygen or sulphur atoms and which is optionally substituted by methyl or ethyl, or by an alkylenedioxyl group, which, together with the carbon atom to which it is attached, forms a further five- or six-membered ring, with the proviso that Q 3 then represents hydrogen or methyl, or 20 A, B and the carbon atom to which they are attached represent C 3 -C 6 -cycloalkyl or C 5 -C 6 -cycloalkenyl in which two substituents together with the carbon atoms to which they are attached represent C 2 -C 4 -alkanediyl, C 2 -C 4 alkenediyl, where optionally one methylene group is replaced by oxygen, or butadienediyl, each of which is optionally monosubstituted by methyl or 25 methoxy, with the proviso that Q 3 then represents hydrogen or methyl, -79 D represents hydrogen, represents C-C 6 -alkyl, C 3 -C 6 -alkenyl, CI-C 4 -alkoxy C 2 -C 3 -alkyl, each of which is optionally mono- to trisubstituted by fluorine or chlorine, represents C 3 -C 7 -cycloalkyl which is optionally monosubstituted by CI-C 2 -alkyl, CI-C 2 -alkoxy or trifluoromethyl and in which optionally one 5 methylene group is replaced by oxygen or sulphur or (but not in the case of the compounds of the formula (I-1)) represents phenyl, pyridyl or benzyl, each of which is optionally mono- or disubstituted by fluorine, chlorine, bromine, C 1 -C 4 -alkyl, CI-C 2 -haloalkyl, C-C 4 -alkoxy or C-C 2 -haloalkoxy, or A and D together represent optionally substituted C 3 -C-alkanediyl in which one 10 methylene group may be replaced by oxygen or sulphur, possible substituents being C-C 2 -alkyl, or A and D (in the case of the compounds of the formula (I-1)) together with the atoms to which they are attached represent one of the groups AD-I to AD-10: N N N AD-I AD-2 AD-3 I I AD-4 AD-5 AD-6 N N IN AD-7 AD-8 AD-9 - 80 AD-10 A and Q 1 together represent C 3 -C 4 -alkanediyl or C 3 -C 4 -alkenediyl, each of which is optionally mono- or disubstituted by identical or different substituents from the group consisting of C-C 2 -alkyl and Ci-C 2 -alkoxy, or Q1 represents hydrogen, 5 Q 2 represents hydrogen, Q 4 , Q 5 and Q 6 independently of one another represent hydrogen or CI-C 2 -alkyl, Q 3 represents hydrogen, Ci-C 4 -alkyl, Ci-C 4 -alkoxy-C 1 -C 2 -alkyl, C-C 4 -alkylthio CI-C 2 -alkyl or optionally methyl- or methoxy-substituted C 3 -C 6 -cycloalkyl in which optionally one methylene group is replaced by oxygen or sulphur, 10 or Q 3 and Q 4 together with the carbon to which they are attached represent a saturated C 5 -C 6 -ring which is optionally mono- or disubstituted by CI-C 4 -alkyl or CI-C 4 -alkoxy and in which optionally one ring member is replaced by oxygen or sulphur, 15 with the proviso that A then represents hydrogen or methyl, G represents chlorine or nitro. 4. Use of a composition according to Claim 1 for controlling insects and/or arachnids, which composition comprises compounds of the formula (I) in which W represents hydrogen, chlorine, bromine, methyl, ethyl, methoxy or ethoxy, 20 X represents chlorine, bromine, methyl, ethyl, propyl, methoxy, ethoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy or cyano, Y represents hydrogen, chlorine, bromine, methyl, trifluoromethyl or - 81 represents the radical v 1 V VI represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, tert-butyl, methoxy, trifluoromethyl or trifluoromethoxy, 5 V 2 represents hydrogen, fluorine, chlorine, methyl, methoxy or trifluoromethyl, Z represents hydrogen, chlorine, bromine, methyl, ethyl, methoxy or ethoxy, CDC represents one of the groups 0 0 A A N B (1), B (2), N 0 D/G G 0 0 A A .N 0 B (3) (4), S G D G 0 0 0 O A A B G B (5), O (6), G QQ 5 Q 6 Q 0 10 A represents hydrogen, represents CI-C 4 -alkyl or CI-C 2 -alkoxy-CI-C 2 -alkyl, each of which is optionally mono- to trisubstituted by fluorine, or represents C 3 -C 6 -cycloalkyl which is optionally monosubstituted by fluorine, methyl or methoxy, B represents hydrogen, methyl or ethyl, or 15 A, B and the carbon atom to which they are attached represent saturated C 5 -C 6 - - 82 cycloalkyl in which optionally one ring member is replaced by oxygen and which is optionally monosubstituted by methyl, trifluoromethyl, methoxy, ethoxy, propoxy, butoxy or isobutoxy, with the proviso that Q 3 then represents hydrogen, or 5 A, B and the carbon atom to which they are attached represent C 5 -C 6 -cycloalkyl which is substituted by an alkylenedioxyl group which contains two not directly adjacent oxygen atoms, with the proviso that Q 3 then represents hydrogen, D represents hydrogen, represents CI-C 4 -alkyl, C 3 -C 4 -alkenyl, CI-C 2 -alkoxy 10 C 2 -C 3 -alkyl or C 3 -C 6 -cycloalkyl in which optionally one methylene group is replaced by oxygen or sulphur, each of which radicals is optionally mono- to trisubstituted by fluorine, or (but not in the case of the compounds of the formula (I-1)) represents phenyl or pyridyl, each of which is optionally mono- or disubstituted by fluorine, chlorine, bromine, methyl, ethyl, 15 n-propyl, isopropyl, methoxy, ethoxy, trifluoromethyl or trifluoromethoxy, or A and D together represent optionally substituted C 3 -C 5 -alkanediyl in which optionally one carbon atom is replaced by oxygen or sulphur and which is optionally mono- or disubstituted by methyl, or 20 A and D (in the case of the compounds of the formula (I-1)) together with the atoms to which they are attached represent the group: N AD-I A and Q' together represent C 3 -C 4 -alkanediyl which is optionally mono- or 25 disubstituted by methyl or methoxy or Q 1 represents hydrogen, Q 2 represents hydrogen, - 83 Q 4 , Q 5 and Q 6 independently of one another represent hydrogen or methyl, Q 3 represents hydrogen, methyl, ethyl or C 3 -C 6 -cycloalkyl, or Q 3 and Q 4 together with the carbon to which they are attached represent a saturated CS-C 6 -ring which is optionally monosubstituted by methyl or methoxy and in 5 which optionally one ring member is replaced by oxygen or sulphur, with the proviso that A then represents hydrogen, G represents chlorine or nitro.
  2. 5. Use of a composition according to Claim I for controlling insects and/or arachnids, which composition comprises compounds of the formula (I) in which 10 W represents hydrogen, chlorine, bromine, methyl, ethyl, methoxy or ethoxy, X represents chlorine, bromine, methyl, ethyl, propyl, methoxy, ethoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy or cyano, Y represents hydrogen, chlorine, bromine, methyl, trifluoromethyl or represents the radical 15 V VI represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, tert-butyl, methoxy, trifluoromethyl or trifluoromethoxy, V2 represents hydrogen, fluorine, chlorine, methyl, methoxy or trifluoromethyl, Z represents hydrogen, methyl, chlorine or bromine, 20 CDC represents one of the groups 0 0 A A B (1), B (2), N 0 / G G D 0 0 -84 A represents hydrogen, represents C-C 4 -alkyl or C-C 2 -alkoxy-C-C 2 -alkyl, each of which is optionally mono- to trisubstituted by fluorine, or represents C 3 -C 6 -cycloalkyl which is optionally monosubstituted by fluorine, methyl or methoxy, 5 B represents hydrogen, methyl or ethyl, or A, B and the carbon atom to which they are attached represent saturated C 5 -C 6 cycloalkyl in which optionally one ring member is replaced by oxygen and which is optionally monosubstituted by methyl, trifluoromethyl, methoxy, ethoxy, propoxy, butoxy or isobutoxy, 10 D represents hydrogen, G represents chlorine.
  3. 6. Method for controlling insects and/or arachnids, characterized in that compositions as defined in Claim 1 are allowed to act on insects and/or arachnids and/or their habitat.
  4. 7. Use of a composition according to Claim I for controlling insects and/or arachnids, 15 where the crop plant compatibility-improving compound is cloquintocet-mexyl, mefenpyr-diethyl, isoxadifen-ethyl, furilazole, dichlormid, fenclorim or the compound of the formula (IIe-5).
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MX2007000636A (en) 2009-02-11
EP1773126A1 (en) 2007-04-18
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CA2574199A1 (en) 2006-01-26
JP2008506739A (en) 2008-03-06
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EA200700316A1 (en) 2007-06-29
CN101530101A (en) 2009-09-16

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