WO2010102758A2 - Halogenalkylmethylenoxy-phenyl-substituierte ketoenole - Google Patents
Halogenalkylmethylenoxy-phenyl-substituierte ketoenole Download PDFInfo
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- WO2010102758A2 WO2010102758A2 PCT/EP2010/001392 EP2010001392W WO2010102758A2 WO 2010102758 A2 WO2010102758 A2 WO 2010102758A2 EP 2010001392 W EP2010001392 W EP 2010001392W WO 2010102758 A2 WO2010102758 A2 WO 2010102758A2
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- alkyl
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- 0 C[C@](*)(CC=CN)CC(S)=C(*)C* Chemical compound C[C@](*)(CC=CN)CC(S)=C(*)C* 0.000 description 18
- HTFFABIIOAKIBH-UHFFFAOYSA-N C1CNNCC1 Chemical compound C1CNNCC1 HTFFABIIOAKIBH-UHFFFAOYSA-N 0.000 description 1
- JJGZAXOTVOUUNN-UHFFFAOYSA-N CC(C)(CCC1=O)C(O)=C1c(c(C)c1)c(C)cc1OCC(F)(F)F Chemical compound CC(C)(CCC1=O)C(O)=C1c(c(C)c1)c(C)cc1OCC(F)(F)F JJGZAXOTVOUUNN-UHFFFAOYSA-N 0.000 description 1
- KKHHOQVVBSCUHO-UHFFFAOYSA-N CCOC(C(C)(C)CCC(Cc(c(C)c1)c(C)cc1OCC(F)(F)F)=O)=O Chemical compound CCOC(C(C)(C)CCC(Cc(c(C)c1)c(C)cc1OCC(F)(F)F)=O)=O KKHHOQVVBSCUHO-UHFFFAOYSA-N 0.000 description 1
- CFRCVXKPEZZIAH-UHFFFAOYSA-N CCc(c(CC(O)=O)c1CC)ccc1Br Chemical compound CCc(c(CC(O)=O)c1CC)ccc1Br CFRCVXKPEZZIAH-UHFFFAOYSA-N 0.000 description 1
- MXUMVPROXXFERB-UHFFFAOYSA-N C[N](CCO)(N)I Chemical compound C[N](CCO)(N)I MXUMVPROXXFERB-UHFFFAOYSA-N 0.000 description 1
- RPRMPFMHOQCLKJ-UHFFFAOYSA-N Cc1c(C(C(Cl)=O)=C=O)c(C)cc(OCC(F)(F)F)c1 Chemical compound Cc1c(C(C(Cl)=O)=C=O)c(C)cc(OCC(F)(F)F)c1 RPRMPFMHOQCLKJ-UHFFFAOYSA-N 0.000 description 1
- CCYXBECHVQRDGH-UHFFFAOYSA-N Cc1cc(OCC(F)(F)F)cc(C)c1C(C(N1N2CCCC1)=O)=C2O Chemical compound Cc1cc(OCC(F)(F)F)cc(C)c1C(C(N1N2CCCC1)=O)=C2O CCYXBECHVQRDGH-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/72—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms
- C07C235/76—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
- C07C235/78—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton the carbon skeleton containing rings
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, 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
- A01N43/38—Biocides, 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
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, 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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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
- A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/734—Ethers
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/38—2-Pyrrolones
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/54—Spiro-condensed
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/94—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom spiro-condensed with carbocyclic rings or ring systems, e.g. griseofulvins
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
- C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/10—Spiro-condensed systems
Definitions
- the present invention relates to novel haloalkylmethylenephenyl-substituted ketoenols, to a plurality of processes for their preparation and to their use as pesticides and / or herbicides.
- the invention also provides selective herbicidal compositions which contain haloalkylmethylene-oxy-phenyl-substituted ketoenols on the one hand and a crop plant compatibility-improving compound on the other hand.
- the present invention further relates to the enhancement of the action of pesticides containing in particular haloalkylmethylenoxy-phenyl-substituted ketoenols, by the addition of ammonium or phosphonium salts and optionally penetration promoters, the corresponding agents, processes for their preparation and their use in crop protection as insecticides and / or Acaricides and / or to prevent unwanted plant growth.
- EP-A-0 262 399 and GB-A-2 266 888 disclose similarly structured compounds (3-aryl-pyrrolidine-2,4-diones), of which, however, no herbicidal, insecticidal or acaricidal action has become known.
- Unsubstituted, bicyclic 3-arylpyrrolidine-2,4-dione derivatives (EP-A-355 599, EP-A-415 211 and JP-A-12-053 670) are known to have a herbicidal, insecticidal or acaricidal action and substituted monocyclic 3-arylpyrrolidine-2,4-dione derivatives (EP-A-377 893 and EP-A-442 077).
- EP-A-442 073 polycyclic 3-arylpyrrolidine-2,4-dione derivatives
- EP-A-456 063 EP-A-521 334, EP-A- 596 298, EP-A-613 884, EP-A-613 885, WO 95/01 971, WO 95/26 954, WO 95/20 572, EP-A-0 668 267, WO 96/25 395, WO 96 / 35,664, WO 97/01 535, WO 97/02 243, WO 97/36868, WO 97/43275, WO 98/05638, WO 98/06721, WO 98/25928, WO 99/24437, WO 99/43649 , WO 99/48869, WO 99/55673, WO 01/17972, WO 01/23354, WO 01/74770, WO 03/013249, WO 03/
- ketal-substituted 1-H-arylpyrrolidine-2,4-diones from WO 99/16748 and (spiro) -ketalsubstitutechnisch N-alkoxy-alkoxy-substituted aryl-pyrrolidinedione from JP-A-14 205 984 and Ito M. et al. Bioscience, Biotechnology and Biochemistry 67, 1230-1238, (2003).
- the addition of safeners to ketoenols is also known in principle from WO 03/013249.
- WO 06/024411 discloses herbicidal compositions containing ketoenols.
- 3-aryl- ⁇ ⁇ -dihydrofuranone derivatives having herbicidal, acaricidal and insecticidal properties are known from EP-A-528 156, EP-A-647 637, WO 95/26 954, WO 96/20 196, WO 96 No.
- 3-aryl- ⁇ 3 -dihydrothiphen-on derivatives are known from WO 95/26 345, 96/25 395, WO 97/01 535, WO 97/02 243, WO 97/36 868, WO 98/05638, WO 98/25928, WO 99/16748, WO 99/43649, WO 99/48869, WO 99/55673, WO 01/17972, WO 01/23354, WO 01/74770, WO 03/013249, WO 04/080 962 WO 04/111 042, WO 05/092897, WO 06/029799 and WO 07/096058.
- Phenylpyrone derivatives having herbicidal, acaricidal and insecticidal properties substituted in the phenyl ring are described in EP-A-588 137, WO 96/25 395, WO 96/35 664, WO 97/01 535, WO 97/02 243, WO 97 / 16,436, WO 97/19941, WO 97/36868, WO 98/05638, WO 99/43649, WO 99/48869, WO 99/55673, WO 01/17972, WO 01/74770, WO 03/013249 , WO 04/080 962, WO 04/111 042, WO 05/092897, WO 06/029799 and WO 07/096058. Furthermore, isomeric pyran-3,5-diones in WO 08/071405 and WO 09/074314 described.
- phenyl ring substituted 5-phenyl-l, 3-thiazine derivatives with herbicidal, acaricidal and insecticidal activity are in WO 94/14785, WO 96/2 5395, WO 96/35 664, WO 97/01 535, WO 97 / 02 243, WO 97/02 243, WO 97/36 868, WO 99/43649, WO 99/48869, WO 99/55673, WO 01/17972, WO 01/74770, WO 03/013249, WO 04/080 962 , WO 04/1 11 042, WO 05/092897, WO 06/029799 and WO 07/096058.
- 4-phenyl-substituted [1.2] oxazine-3,5-diones are described as herbicides for the first time in WO 01/17972. Furthermore, 4-acyl-substituted [1.2] oxazine-3,5-diones have been described as pesticides, but especially as herbicides and growth regulators, e.g. in EP-A-394889; WO 92/07837, US 5,728,831 and as herbicides and pesticides in WO03 / 048138.
- W is hydrogen, alkyl, halogen, haloalkyl, alkoxy or haloalkoxy,
- X is alkyl, alkenyl, alkynyl, halogen, alkoxy, haloalkyl, haloalkoxy or cyano, represents hydrogen, alkyl, alkoxy or halogen,
- J 1 and J 2 are each independently of one another hydrogen or halogen and J 3 is halogen or a haloalkyl group
- U is -S-, -S (O) -, -S (O) 2 -, -O-,
- A represents hydrogen, in each case optionally halogen-substituted alkyl, 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,
- B is hydrogen, alkyl or alkoxyalkyl, or
- a and B together with the carbon atom to which they are bonded represent a saturated or unsaturated unsubstituted or substituted cycle optionally containing at least one heteroatom
- D is hydrogen or an optionally substituted radical from the series alkyl, alkenyl, alkynyl, alkoxyalkyl, saturated or unsaturated cycloalkyl in which optionally one or more ring members are replaced by heteroatoms, in each case optionally substituted arylalkyl, aryl, hetarylalkyl or hetaryl stands or
- B and Q 2 together with the atoms to which they are attached, represent a saturated or unsaturated and optionally at least one heteroatom-containing radical which is unsubstituted or substituted in the B, Q 1 part, or
- D and Q * together with the atoms to which they are bonded, represent a saturated or unsaturated and optionally at least one heteroatom-containing, unsubstituted or substituted in the D, Q * part cycle,
- Q! is hydrogen, alkyl, alkoxyalkyl, optionally substituted cycloalkyl, in which optionally a methylene group is replaced by oxygen or sulfur or represents optionally substituted phenyl,
- Q ⁇ , Q ⁇ are> Q ⁇ and Q ⁇ are independently hydrogen or alkyl
- Q ⁇ is hydrogen, in each case optionally substituted alkyl, alkoxy,
- a and Q ⁇ together with the carbon atom to which they are attached represent a saturated or unsaturated unsubstituted or substituted cycle optionally containing at least one heteroatom, or
- a and Q5 together with the carbon atom to which they are attached, represent a saturated or unsaturated unsubstituted or substituted cycle, optionally containing at least one heteroatom,
- G is hydrogen (a) or one of the groups
- E is a metal ion equivalent or an ammonium ion
- L is oxygen or sulfur
- M is oxygen or sulfur
- R.1 is in each case optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl or optionally substituted by halogen, alkyl or alkoxy-substituted cycloalkyl which may be interrupted by at least one heteroatom, in each case optionally substituted phenyl, phenylalkyl, hetaryl , Phenoxyalkyl or
- R.2 is in each case optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl or in each case optionally substituted cycloalkyl, phenyl or benzyl
- R 1, R 4 and R 4 independently of one another are each optionally halogen-substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio, cycloalkylthio or in each case optionally substituted phenyl, benzyl, phenoxy or phenylthio,
- R ⁇ and R ⁇ are each independently hydrogen, each optionally halogen-substituted alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, optionally substituted phenyl, optionally substituted benzyl, or together with the N-atom to which they are attached , stand for a possibly interrupted by oxygen or sulfur cycle.
- the compounds of the formula (I) can be present in different compositions as geometric and / or optical isomers or mixtures of isomers, which can optionally be separated in a customary manner. Both the pure isomers and the isomer mixtures can be used in inventive compositions and can be increased in their effect by ammonium or phosphonium salts according to the invention. In the following, for the sake of simplicity, compounds of the formula (I) are always mentioned, although both the pure compounds and optionally also mixtures with different proportions of isomeric compounds are meant.
- A, B, D, G, Q 1 , Q 2 , Q 5 , Q 6 , U, W, X, Y and Z are as defined above.
- A, B, D, E, L, M, W, X, Y, Z, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 have the meanings given above. Taking into account the various meanings (a), (b), (c), (d), (e), (f) and (g) of the group G, the following main structures (I-2-a) to (I -2-g), if CKE stands for the group (2),
- A, B, E, L, M, W, X, Y, Z, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 have the abovementioned meaning.
- A, B, E, L, M, W, X, Y, Z, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 have the meaning given above.
- the compounds of formula (1-4) may be present in the two isomeric forms of formulas (I-4-A) and (I-4-B), depending on the position of substituent G,
- the compounds of the formulas (I-4-A) and (I-4-B) can be present both as mixtures and in the form of their pure isomers. Mixtures of the compounds of the formulas (I-4-A) and (I-4-B) can optionally be separated in a manner known per se by physical methods, for example by chromatographic methods.
- A, D, E, L, M, W, X, Y, Z, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 have the meanings given above.
- A, E, L, M, W, X, Y, Z, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 have the meanings given above.
- the compounds of the formula (1-6) may be present in the two isomeric forms of the formulas (I-6-A) and (I-6-B), depending on the position of the substituent G,
- the compounds of the formulas (I-6-A) and (I-6-B) can be present both as mixtures and in the form of their pure isomers. Mixtures of the compounds of the formulas (I-6-A) and (I-6-B) can optionally be separated by physical methods, for example by chromatographic methods.
- A, B, Ql, Q 2 , E, L, M, W, X, Y, Z, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 have the meanings given above.
- the compounds of formula (1-7) may be present in the two isomeric forms of formulas (I-7-A) and (I-7-B), respectively, depending on the position of substituent G, which is indicated by the dashed line in FIG Formula (1-7) should be expressed:
- the compounds of the formulas (1-7 -A) or (1-7 -B) can be present both as mixtures and in the form of their pure isomers. Mixtures of the compounds of the formulas (I-7-A) and (I-7-B) can optionally be separated by physical methods, for example by chromatographic methods.
- A, B, U nd R 7 are as defined above E, L, M, Q 5, Q 6, U, W, X, Y, Z, R 1, R 2, R 3, R 4, R ⁇ , R6 have.
- the compounds of the formula (1-8) may be present in the two isomeric formulas (I-8-A) and (I-8-B), depending on the position of the substituent G,
- the compounds of the formulas (1-8-A) and (1-8-B) can be present both as mixtures and in the form of their pure isomers. Mixtures of the compounds of the formula (1-8-A) and (1-8-B) can optionally be separated in a manner known per se by physical methods, for example by chromatographic methods.
- A, D, E, L, M, W, X, Y, Z, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 have the meanings given above.
- the compounds of formula (1-9) may be present in the two isomeric forms of formulas (I-9-A) and (I-9-B), depending on the position of substituent G, represented by the dashed line in the formula (1-9) should be expressed.
- the compounds of the formulas (I-9-A) and (I-9-B) can be present both as mixtures and in the form of their pure isomers. Mixtures of the compounds of the formulas (I-9-A) and (I-9-B) can optionally be separated in a manner known per se by physical methods, for example by chromatographic methods. For reasons of clarity, only one of the possible isomers will be listed below. This does not exclude that the compounds may optionally be present in the form of the isomer mixtures or in the other isomeric form.
- A, B, D, E, L, M, Ql, Q 2 , W, X, Y, Z, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 have the meanings given above ,
- the compounds of the formula (I-10) may be present in the two isomeric forms of the formulas (I-10A) and (I-10-B), depending on the position of the substituent G,
- the compounds of the formulas (I-10-A) and (I-10-B) can be present both as mixtures and in the form of their pure isomers. Mixtures of the compounds of the formulas (I-10-A) and (I-10-B) can optionally be separated in a manner known per se by physical methods, for example by chromatographic methods.
- A, B, E, L, M, Q 1 , Q 2 , W, X, Y, Z, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 have the meanings given above.
- the compounds of formula (I-11) may be present in the two isomeric forms of formulas (I-1-A) and (I-11-B), depending on the position of substituent G, which may be represented by the dashed line in the formula (I-11) is to be expressed.
- the compounds of the formulas (I-I-A) and (I-I-B) can be present both as mixtures and in the form of their pure isomers. Mixtures of the compounds of the formulas (I-II-A) and (I-H-B) can optionally be separated in a manner known per se by physical methods, for example by chromatographic methods.
- A, B, D, W, X, Y and Z have the meanings given above,
- A, B, D, W, X, Y and Z have the meanings given above,
- R 8 is alkyl (preferably C 1 -C 6 -alkyl)
- A, B, W, X, Y, Z and R ° have the meanings given above,
- A, B, W, X, Y, Z and R ⁇ have the meanings given above, and
- V is hydrogen, halogen, alkyl (preferably C j -Cg -alkyl) or alkoxy (preferred
- W, X, Y and Z have the meanings given above, and
- Hal is halogen (preferably chlorine or bromine),
- Hal, W, X, Y and Z have the meanings given above,
- A, B, Q1, Q1, W, X, Y and Z are as defined above,
- A, B, Q1, Q1, W, X, Y and Z are as defined above, and
- R 8 is alkyl (in particular C 1 -C 8 -alkyl),
- A, B, Q5, Q6 ; U, W, X, Y and Z are as defined above,
- A, B, Q ⁇ , Q6, U, W, X, Y and Z are as defined above
- R 8 is alkyl (preferably C 1 -C 6 -alkyl)
- Hal, W, X, Y and Z have the meanings given above,
- W, X, Y and Z are as defined above,
- U 1 is NH 2 or OR 8 , where R 8 has the abovementioned meaning
- A, D, W, X, Y, Z and R 1 have the abovementioned meaning, if appropriate in the presence of a diluent and if appropriate in the presence of a base.
- A, B, D, Q1, Q2, W, X, Y and Z have the meanings given above,
- A, B, D, Q1, Q2, W, X, Y and Z have the meanings given above,
- R 8 is alkyl (preferably C i -Cg -alkyl), in the presence of a diluent and in the presence of a base intramolecularly condensed.
- A, B, Q1, Q1, W, X, Y and Z have the meanings given above, if one
- A, B, Q1, Q2, W, X, Y and Z are as defined above, and
- R 8 is alkyl (preferably C 1 -C 6 -alkyl), optionally in the presence of a diluent and optionally in the presence a base.
- A, B, D, W, X, Y and Z have the meanings given above,
- A, B, D, W, X, Y and Z have the meanings given above,
- R 8 is alkyl (preferably C i -Cg -alkyl),
- Hal is halogen (especially chlorine or bromine)
- R 2 and M have the meanings given above,
- R 4 and R 5 have the meanings given above, and
- Hal is halogen (especially chlorine or bromine),
- Me for a monovalent or divalent metal preferably an alkali or alkaline earth metal such as lithium, sodium, potassium, magnesium or calcium
- a monovalent or divalent metal preferably an alkali or alkaline earth metal such as lithium, sodium, potassium, magnesium or calcium
- a ammonium preferably an alkali or alkaline earth metal such as lithium, sodium, potassium, magnesium or calcium
- R. 10, R, R 2 independently of one another represent hydrogen or alkyl (preferably C j -Cg-alkyl),
- halogenated alcohols e.g. Trifluoroethanol of the formula (XXVI)
- a solvent in the presence of a copper salt (e.g., Cu-I-J) and in the presence of a base (e.g., potassium tert-butylate, sodium hydride) exchanges the bromine or iodine atom.
- a copper salt e.g., Cu-I-J
- a base e.g., potassium tert-butylate, sodium hydride
- novel compounds of the formula (I) have very good activity as pesticides, preferably as insecticides, acaricides and / or herbicides.
- the safeners are preferably selected from the group consisting of:
- n A is a natural number from 0 to 5, preferably 0 to 3;
- R A ' is halogen, (Ci-C 4 ) alkyl, (C r C 4 ) alkoxy, nitro or (C, -C 4 ) haloalkyl;
- W A is an unsubstituted or substituted divalent heterocyclic radical from the group of the unsaturated or unsaturated five-membered ring heterocycles having 1 to 3 hetero ring N and O groups, wherein at least one N atom and at most one O atom is contained in the ring, preferably a rest from the group
- n A is 0 or 1;
- R A 2 is OR A 3 , SR A 3 or NR A 3 R A "or a saturated or unsaturated 3- to 7-membered heterocycle having at least one N atom and up to 3 heteroatoms, preferably from the group O and S, which is connected via the N-atom to the carbonyl group in (SI) and is unsubstituted or substituted by radicals from the group (Ci-C 4) AIlCyI, (CpC 4) alkoxy or optionally substituted phenyl, preferably a radical of the formula oR a 3 , NHR A 4 or N (CH 3 ) 2 , in particular of the formula OR A 3 ;
- R A 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having a total of 1 to 18 C atoms;
- R A 4 is hydrogen, (C r C 6 ) alkyl, (C r C 6 ) alkoxy or substituted or unsubstituted phenyl;
- R A 5 is H, (Ci-Cg) alkyl, (C r C g ) haloalkyl, (Ci-C 4 ) alkoxy (C 1 -C 8 ) AIlCyI, cyano or COOR A 9 , wherein R A 9 is hydrogen, ( Ci-Cg) alkyl, (Ci-Cg) haloalkyl, (C r C 4 ) alkoxy (C r C 4 ) alkyl, (C r C 6 ) hydroxyalkyl, (C 3 -Ci 2 ) cycloalkyl or tri- (C r C 4) -alkyl-silyl;
- R A 6, R A 7 R A 8 are identical or different hydrogen, (C r C 8) alkyl, (C r C 8) haloalkyl, (C3-Ci2) cycloalkyl or substituted or unsubstituted phenyl;
- dichlorophenylpyrazolecarboxylic acid S l b
- compounds such as ethyl 1- (2,4-dichlorophenyl) -5-methyl-pyrazole-3-carboxylate (S 1 -2), 1- (2,4-dichlorophenyl) - Ethyl 5-isopropyl-pyrazole-3-carboxylate (S 1-3), 1 - (2,4-dichlorophenyl) -5- (1, 1-dimethyl-ethyl) -pyrazole-3-carboxylic acid ethyl ester (Sl-4) and related compounds as described in EP-A-333,131 and EP-A-269,806;
- S l d compounds of the type of the triazolecarboxylic acids (S l d ), preferably compounds such as fenchlorazole (ethyl), ie l- (2,4-dichlorophenyl) -5-richlormethyl (lH) -1, 2,4-triazole-3 -carboxylic acid ethyl ester (Sl-7), and related compounds as described in EP-A-174 562 and EP-A-346 620;
- R B ' is halogen, (C r C 4 ) alkyl, (C r C 4 ) alkoxy, nitro or (C, -C 4 ) haloalkyl;
- n B is a natural number from 0 to 5, preferably 0 to 3;
- R B 2 is OR B 3 , SR B 3 or NR B 3 R B 4 or a saturated one
- R B 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having a total of 1 to 18 C atoms;
- R B 4 is hydrogen, (Ci-C ⁇ JAlkyl, (C r C 6 ) alkoxy or substituted or unsubstituted phenyl;
- T B is a (C] or C 2) -alkanediyl chain which is unsubstituted or substituted with one or two carbonyl (Ci-C 4) alkyl radicals or by [(C r C 3) alkoxy];
- Rc 1 is (C r C 4 ) alkyl, (C r C 4 ) haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) haloalkenyl, (C 3 -C 7 ) cycloalkyl, preferably dichloromethyl;
- Rc 2 , Rc 3 are identical or different hydrogen, (C r C 4 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, (C r C 4 ) haloalkyl, (C 2 -C 4) haloalkenyl, (C r C 4) alkylcarbamoyl (C r C4) alkyl, (C 2 -C 4) Alkenylcarbamoy 1- (C, -C 4) alkyl, (C, -C 4) alkoxy (C -C 4 ) alkyl, dioxolanyl- (Ci-C 4 ) alkyl, thiazolyl, furyl, furylalkyl, thienyl, piperidyl, substituted or unsubstituted phenyl, or R 0 2 and Rc 3 together form a substituted or unsubstituted heterocyclic ring,
- R-29148 (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) from Stauffer (S3-2),
- Benoxacor (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (S3-4),
- PPG-1292 N-allyl-N - [(l 5 3-dioxolan-2-yl) -methyl] -dichloroacetamide
- X D is CH or N
- R D 1 is CO-NR D 5 R D 6 or NHCO-R D 7 ;
- R D 2 is halogen, (C, -C 4) haloalkyl, (C, -C 4) haloalkoxy, nitro, (C r C4) alkyl, (C, -C 4) alkoxy, (C r C4) alkylsulfonyl , (C r C 4 ) alkoxycarbonyl or (C r C 4 ) alkylcarbonyl;
- R D 3 is hydrogen, (C 1 -C 4 ) alkyl, (C 2 -C 4 ) alkenyl or (C 2 -C 4 ) alkynyl;
- R D 4 is halogen, nitro, (C r C4) alkyl, (C, -C 4) haloalkyl, (C, -C 4) haloalkoxy,
- R D 5 is hydrogen, (C 1 -C 6 ) alkyl, (C 3 -C 6 ) cycloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 5 -C 6 ) cycloalkenyl , Phenyl or 3- to 6-membered heterocyclyl containing v D
- R D 6 is hydrogen, (C r C 6 ) alkyl, (C 2 -C 6 ) alkenyl or (C 2 -C 6 ) alkynyl, where the last three radicals are represented by v D radicals from the group consisting of halogen, hydroxy, (C 1 -C 4 ) AlClI, (C 1 -C 4 ) alkoxy and (C 1 -C 4 ) alkylthio, or
- R D 5 and R D 6 together with the nitrogen atom carrying them form a pyrrolidinyl or piperidinyl radical;
- R D 7 is hydrogen, (C r C 4 ) alkylamino, di- (C r C 4 ) alkylamino, (C r C 6 ) alkyl,
- (C 3 -C 6 ) cycloalkyl where the 2 last-mentioned radicals by v D substituents selected from the group consisting of halogen, (C r C 4 ) alkoxy, (C r C 6 ) haloalkoxy and (C r C 4 ) alkylthio and in the case of cyclic Radicals are also substituted by (C 1 -C 4 ) alkyl and (C 1 -C 4 ) haloalkyl;
- n D 0, 1 or 2;
- n D is 1 or 2;
- v D is O, 1, 2 or 3;
- R D 4 is halogen, (C r C 4 ) alkyl, (C r C 4 ) alkoxy, CF 3,
- v D 0, 1, 2 or 3;
- Acylsulfamoylbenzoeklareamide for example, the following formula (S4 b ), for example, are known from WO-A-99/16744,
- R 8 and R D D 9 are independently hydrogen, (DC 8) alkyl, (C 3 -C 8) cycloalkyl, (C 3 - C 6) alkenyl, (C 3 -C 6) alkynyl,
- R D 4 is halogen, (C 1 -C 4 ) AlCl y, (C r C 4 ) alkoxy, CF 3
- n D 1 or 2;
- Ethyl 3,4,5-triacetoxybenzoate 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicyclic acid, 2-hydroxycinnamic acid, 1,2-dihydro-2-oxo-6-trifluoromethylpyridine 3-carboxamide, 2,4-dichlorocinnamic acid, as described in WO-A-2004/084631, WO-A-2005/015994, WO-A-2005/016001.
- R- E 1 , R E 2 are each independently halogen, (C r C 4 ) alkyl, (Ci-Q) alkoxy, (Ci-C 4 ) haloalkyl, (Ci-C 4 ) alkylamino, di- (C r C 4 ) alkylamino, nitro;
- a E is COOR E 3 or COSR E 4
- R E 3, R E 4 are independently hydrogen, (C r C4) alkyl, (C 2 -C 6) alkenyl, (C 2 -C 4) alkynyl, cyanoalkyl, (C r C 4) haloalkyl, phenyl, Nitrophenyl, benzyl, halobenzyl, pyridinylalkyl and alkylammonium,
- n E ! is 0 or 1 ⁇ E , ⁇ E are independently 0, 1 or 2,
- Methyl diphenylmethoxyacetate (CAS No. 41858-19-9) (S7-1).
- R F 1 is halogen, (C 1 -C 4 ) AlCl y, (C r C 4 ) haloalkyl, (C 1 -C 4 ) alkoxy, (C r C 4 ) haloalkoxy, nitro, (C r C 4 ) alkylthio, (C r C 4 ) -alkylsulfonyl, (C r C 4 ) alkoxycarbonyl, optionally substituted. Phenyl, optionally substituted phenoxy,
- R F 2 is hydrogen or (C, -C 4 ) alkyl
- R F 3 is hydrogen, (C r C g ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, or aryl, wherein each of the aforementioned C-containing radicals unsubstituted or by one or more, preferably up to three identical or different radicals from the group consisting of halogen and alkoxy are substituted, or their salts,
- n F is an integer from 0 to 2
- R F 1 is halogen, (C r C 4 ) alkyl, (C r C 4 ) haloalkyl, (C r C 4 ) alkoxy, (C, -C 4 ) haloalkoxy,
- R F 2 is hydrogen or (C r C 4 ) alkyl
- R F 3 is hydrogen, (C 1 -C 8 ) AlCl yI, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, or aryl, where each of the abovementioned C-containing radicals is unsubstituted or substituted by one or more preferably up to three identical or different radicals from the group consisting of halogen and alkoxy is substituted, mean, or their salts.
- S9 Agents from the class of 3- (5-tetrazolylcarbonyl) -2-quinolones (S9), e.g. 1,2-Dihydro-4-hydroxy-1-ethyl-3- (5-tetrazolylcarbonyl) -2-quinolone (CAS Reg. 219479-18-2), 1, 2-dihydro-4-hydroxy-1 -methyl-3- (5-tetrazolyl-carbonyl) -2-quinolone (CAS No. 95855-00-8) as described in WO-A-1999/000020.
- S9 1,2-Dihydro-4-hydroxy-1-ethyl-3- (5-tetrazolylcarbonyl) -2-quinolone (CAS Reg. 219479-18-2), 1, 2-dihydro-4-hydroxy-1 -methyl-3- (5-tetrazolyl-carbonyl) -2-quinolone (CAS No. 95855-00-8) as described in WO-A-1999/000020.
- R G 1 is halogen, (C 1 -C 4 ) alkyl, methoxy, nitro, cyano, CF 3 , OCF 3
- n G is an integer from 0 to 4,
- R G (C r C 16 ) alkyl (C 2 -C 6 ) alkenyl, (C 3 -C 6 ) cycloalkyl, aryl; Benzyl, halobenzyl,
- R G 3 is hydrogen or (C, -C 6 ) alkyl.
- Si l) active substances of the type of oxyimino compounds (Si l) used as seed dressing are known, such.
- Si l) active substances of the type of oxyimino compounds (Si l) used as seed dressing are known, such.
- B. "Oxabetrinu" ((Z) -1,3-dioxolanylmethoxyimino (phenyl) acetonitrile) (SII) 5 which is known as a seed dressing safener for millet against damage by metolachlor
- Cyometrinil or “CGA-43089” ((Z) -cyanomethoxyimino (phenyl) acetonitrile) (S1-3), which is known as a seed dressing safener for millet against damage by metolachlor.
- Isothiochromanone (S12) class agents e.g. Methyl - [(3-oxo-
- Naphthalene anhydride (1,8-naphthalenedicarboxylic anhydride) (S13-1), which is known as a seed safener for corn against damage by thiocarbamate herbicides.
- MG 191 (CAS Reg. No. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S 13-5) from Nitrokemia, which is known as safener for corn,
- active substances primarily used as herbicides, but also having safener action on crop plants, e.g.
- W is preferably hydrogen, C 1 -C 6 -alkyl, halogen, C 1 -C 6 -alkoxy, C 1 -C 4 -halogenoalkyl or C 1 -C 4 -haloalkoxy,
- X is preferably halogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy or cyano,
- Y preferably represents hydrogen, halogen, Cj-Cg alkyl or C j -Cö alkoxy,
- Z is preferably a group
- J 1 and J 2 are preferably each independently hydrogen, fluorine or chlorine, and J 3 bevozugt halogen or C r C 4 haloalkyl,
- CKE preferably stands for one of the groups
- U is preferably -S-, -S (O) -, -S (O) 2-, -O-,
- n is the number O, 1 or 2
- A preferably represents hydrogen or respectively optionally halogen-substituted C 1 -C 1 2 alkyl, C 3 -C 8 alkenyl, C ⁇ Cio-alkoxy-Ci-Cg-alkyl, Ci-Cjo-alkylthio-Ci-Cg- C 3 -C 9 -cycloalkyl, optionally substituted by halogen, C 1 -C -alkenyl or C 1 -C -alkoxy, in which optionally one or two non-adjacent ring members are replaced by oxygen and / or sulfur or in each case optionally by halogen, C 1 -C 6 -alkyl, C 1 -C 6 -halogenoalkyl, C 1 -C 6 -alkoxy, C 1 -C 9 -halogenalkoxy, cyano or nitro-substituted phenyl, naphthyl, hetaryl having 5 to 6 ring atoms (for example furany
- B is preferably hydrogen, C 1 -C 2 -alky 1 or C 1 -C 9 -alkoxy-C 1 -CG-alky 1 or
- A, B and the carbon atom to which they are attached preferably represent saturated C 3 C j o-cycloalkyl or unsaturated C5-C ⁇ ) -cycloalkyl in which optionally one ring member is replaced by nitrogen, oxygen or sulfur and which are optionally mono- or disubstituted by Cj-Cg-alkyl, C ⁇ -CG-alkoxy, C3-Cg-alkenyloxy, C j -Cg- -alkoxy-C 1 -CG alkyl, C3-C ⁇ ) cycloalkyl, C 1 -Cg- haloalkyl, C2-Cg haloalkoxy, C 1 -C 6 alkoxy-C 1 -C 4 alkoxy substituted, where the radicals mentioned above come into question also as N-substituent, or A, B and the carbon atom to which they are attached are preferably C 3 -C 6 -cycloalkyl which is alkylenediyl optionally
- A, B and the carbon atom to which they are attached are preferably C 3 -C 6 -cycloalkyl or C 5 -C 8 -cycloalkenyl in which two substituents together with the carbon atoms to which they are attached are each optionally substituted by C 1 -C 4 -cycloalkyl -Cg alkyl, C j -Cg alkoxy or halogen substituted C2-Cg alkanediyl, C2-Cg alkenediyl or
- D preferably represents hydrogen, respectively optionally halogen-substituted CJ-C j 2-alkyl, C3-Cg alkenyl, C3-C8 alkynyl, Cj-C jQ alkoxy-Ci-Cg-alkyl, optionally substituted by halogen, C j ⁇ -C alkyl, C ⁇ alkoxy or C j -C j ⁇ -C haloalkyl-substituted C3-
- Cg-cycloalkyl in which optionally one ring member is replaced by oxygen or sulfur or in each case optionally substituted by halogen, Cj-Cg-alkyl, C j -CG haloalkyl, C j -CG-alkoxy, C j -CG-haloalkoxy, cyano or Nitro substituted phenyl, hetaryl having 5 or 6 ring atoms (for example, furanyl, imidazolyl, pyridyl, thiazolyl, pyrazolyl, pyrimidyl, pyrrolyl, thienyl or triazolyl), phenyl-Cj-Cg-alkyl or hetaryl-C j -Cg- alkyl 5 or 6 ring atoms (for example, furanyl, imidazolyl, pyridyl, thiazolyl, pyrazolyl, pyrimidyl, pyrrolyl, thien
- a and D together are preferably each optionally substituted C3-C6-alkanediyl or C3-C6-alkenediyl, wherein optionally a methylene group is replaced by a carbonyl group, oxygen or sulfur, and
- Ci-Cjo-alkyl Cj-Cg alkoxy, Cj-Cg-alkylthio, C3-C 7 -cycloalkyl, phenyl or benzyloxy, or a further C3-C6-Alkandiylgrupp réelle, C3 -C6-alkenediyl or a Butadienylgrupp réelle, which is optionally substituted by Ci -Cg-alkyl or in which optionally two adjacent substituents with the carbon atoms to which they are attached, form another saturated or unsaturated cycle with 5 or 6 ring atoms (in the case of the compound of the formula (I-1), A and D are then in common sam with the atoms to which they are attached, for example, for the groups AD-I to AD-IO mentioned below, which may contain oxygen or sulfur, or in which optionally one of the following groups
- a and Q! preferably together with the carbon atoms to which they are attached, each optionally optionally mono- or disubstituted, identically or differently, by halogen, hydroxyl, by in each case optionally monosubstituted to trisubstituted by identical or different substituents C 1 -C 8 -alkyl, C j -Cg-alkenyl, Cj-Cg-alkoxy, Cj-Cg-alkylthio, C ⁇ -C ⁇ -cycloalkyl or substituted by in each case optionally mono- to trisubstituted by identical or different halogen, C j -Cg-alkyl or Ci-Cg-alkoxy Benzyloxy or phenyl substituted C3-Cg-alkanediyl or C ⁇ Cg-alkenediyl, which also optionally one of the following groups
- Ci -C2-alkanediyl group or is bridged by a Ci -C2-alkanediyl group or by an oxygen atom or
- B and Q 2 together preferably represent optionally substituted by Ci-C 2 alkyl substituted C r C 3 -alkanediyl which may optionally be interrupted by oxygen, or
- D and Q! together are preferably C3-C6-alkanediyl which may be monosubstituted or disubstituted by identical or different substituents and substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, or
- Q 1 preferably represents hydrogen, C j -Cö alkyl, C ⁇ -CG-alkoxy-C ⁇ -C 2 alkyl, optionally substituted by fluorine, chlorine, Cj-C ⁇ alkyl, C j -C 2 haloalkyl or C] - C4-alkoxy-substituted C3-C7-cycloalkyl, where appropriate, a methylene group by oxygen or
- Q 1 and Q 2 independently of one another are preferably hydrogen or C 1 -C 4 -alkyl
- Q 3 is preferably hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkoxy-C 1 -C 2 -alkyl, C 1 -C 6 -alkylthio-C 1 -C 2 -alkyl optionally substituted by Ci-C 4 alkyl or Ci-C4-alkoxy-substituted C3-Cg-cycloalkyl, wherein optionally one or two methylene groups are replaced by oxygen or sulfur or optionally by halogen, Ci-C4-alkyl, Ci -C4-alkoxy , Cj ⁇ -haloalkyl, Cj ⁇ -haloalkoxy, cyano or nitro substituted phenyl, or
- Q 1 and Q are preferably attached to the carbon atom to which they are attached optionally substituted by C j -CG alkyl, Cj-Cg-Allcoxy or Ci-C2-haloalkyl CSS C ⁇ -ring in which optionally one ring member is replaced by oxygen or sulfur,
- Q.sup.11 and Q.sup.4 together with the carbon atom to which they are bonded are preferably C, -C.sub.10 alkyl, C.sub.1 -C.sub.10 alkoxy or C.sub.1 -C.sub.2 -C.sub.2 haloalkyl-substituted saturated or unsaturated C.sub.1-Cy rings which optionally one or two ring members are replaced by oxygen or sulfur,
- a and Q ⁇ are preferably together with the carbon atoms to which they are bonded, represent a saturated or unsaturated, optionally j by C-C4-alkyl, C] -C4-alkoxy or Ci-C2-haloalkyl-substituted C3-C7-ring in which optionally one or two ring members are replaced by oxygen or sulfur,
- a and Q ⁇ are preferably together with the carbon atoms to which they are bonded, substituted for a saturated or unsaturated, optionally substituted by C j-C4 alkyl, Cj-C4-alkoxy or Ci-C2-haloalkyl, C3-C7 ring in which optionally a ring member is replaced by oxygen or sulfur,
- G is preferably hydrogen (a) or one of the groups
- E is a metal ion equivalent or an ammonium ion
- M is oxygen or sulfur.
- R! is preferably in each case optionally halogen-substituted Ci-C20-alkyl, C2-
- phenyl optionally substituted by halogen, nitro, cyano, C j -Cg -alkyl, Cj-Cg-alkoxy, Cj-Cg-haloalkyl or C j -Cg -haloalkoxy-Ci-Cg-alkyl,
- halogen or Cj-Cg-alkyl 5- or 6-membered hetaryl for example, pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl
- Cj-Cg-alkyl 5- or 6-membered hetaryl for example, pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl
- R ⁇ preferably represents in each case optionally halogen-substituted Ci -C 20 "alkyl, C 2 - C 2 o-alkenyl, C j -CG-alkoxy ⁇ -CG-alkyl, poly-C j -CG-alkoxy-C2-C8 alkyl,
- R ⁇ preferably represents optionally halogen-substituted C j -CG alkyl or in each case optionally substituted by halogen, Cj-Cg alkyl, Cj-Cg alkoxy, Cj-C ⁇ haloalkyl, Cj-C4 haloalkoxy, cyano or nitro substituted phenyl or benzyl,
- R ⁇ and R ⁇ are preferably independently of one another represent in each case optionally halogen-substituted Cj-Cg alkyl, Cj-Cg-alkoxy, C j -CG-alkylamino, di- (C j -CG-alkyl) amino,
- Haloalkyl, C j -C haloalkoxy, nitro or cyano-substituted phenyl, phenyl-CJ-C4-alkyl, hetaryl-Ci-C 4 alkyl, or only in the case of C NR 13 group phenyl-C JC 4 - alkoxy or hetaryl-Cj-C ⁇ alkoxy,
- R 14a stent preferably j is hydrogen or C -CG alkyl or
- R 1 and R 1 are together preferably C 1 -C 4 -alkanediyl optionally substituted by C 1 -C 4 -alkyl, which may optionally be interrupted by oxygen or sulfur,
- R 1 a and R 16a together preferably represent a C 2 -C 4 -alkanediyl radical or C 4 -alkanediyl radical which is optionally substituted by C 1 -C 6 -alkyl, C 1 -C 8 -halogenoalkyl or by halogen, C 1 -C 8 -alkyl, C 1 -C 4 Haloalkyl, Cj-Cg-alkoxy, C1-C4-haloalkoxy, nitro or cyano-substituted phenyl is substituted,
- Rl ⁇ a ⁇ a nd R independently of one another preferably represent hydrogen, represent optionally halogen-substituted C j -CG-alkyl, or represents optionally halogen-, C j -Cg- alkyl, Cj-Cg-alkoxy, C j -C4- Haloalkyl, Cj-C4-haloalkoxy, nitro or cyano substituted phenyl or
- R ⁇ a and Rl ** a are preferably a carbonyl group or optionally halogen, C 1 -C 4 -alkyl or C j - C4-alkoxy-substituted C5-C7-cycloalkyl in which optionally a methylene group is replaced by oxygen or sulfur,
- R 19a and R ⁇ Oa are each independently preferably C j -C j g alkyl, C2-C ⁇ ) alkenyl, Cj-C ⁇ o alkoxy, Cj-CIQ-alkylamino, CSS CIQ-alkenylamino, di- ( Ci-C ⁇ ) -alkyl) amino or di- (C3-C j Q -alkenyl) amino.
- halogen is fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine.
- W is particularly preferably hydrogen, fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 2 -haloalkyl or C 1 -C 2 -haloalkoxy,
- X particularly preferably represents chlorine, bromine, iodine, Cj-C4 alkyl, C2-C4-alkenyl, C2-C4 alkynyl, C] -C4-alkoxy, Ci-C2-haloalkyl, Ci-C2-haloalkoxy or cyano, .
- Y is particularly preferably hydrogen, methyl, ethyl, fluorine, chlorine, bromine, iodine, methoxy or ethoxy,
- Z is particularly preferably the group
- j1 and fi particularly preferably each independently of one another stand for hydrogen, fluorine or chlorine and J- * stands for fluorine, chlorine trichloromethyl, difluoromethyl, difluorochloromethyl, dichlorofluoromethyl or trifluoromethyl,
- CKE particularly preferably stands for one of the groups
- B particularly preferably represents hydrogen, C 1 -C 4 -alkyl or C 1 -C 2 -alkoxy-C 1 -C 2 -alkyl or
- A, B and the carbon atom to which they are attached are particularly preferably saturated or unsaturated C ⁇ -C ⁇ -cycloalkyl, in which optionally one ring member is replaced by nitrogen, oxygen or sulfur and which optionally once to twice by C ⁇ -Cg-alkyl , C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl, trifluoromethyl, C j -Cg -alkoxy,
- A, B and the carbon atom to which they are attached are particularly preferably C5-C6-cycloalkyl which is substituted by an optionally one or two oxygen or sulfur atoms not directly adjacent or optionally substituted by methyl or ethyl alkylenediyl or by an alkylenedioxy or is substituted by an alkylenedithiol group which forms, with the carbon atom to which it is bonded, another five- or six-membered ring with the proviso that Cy is then particularly preferably hydrogen or methyl, or
- A, B and the carbon atom to which they are attached are particularly preferably C 3 -C 9 -cycloalkyl or C 5 -C 6 -cycloalkenyl in which two substituents together with the carbon atoms to which they are attached are each optionally substituted by C j -C 2 alkyl or C 1 -C 2 alkoxy substituted C 2 -C 4 alkanediyl, C 2 -C 4 alkenediyl or
- D particularly preferably represents hydrogen, in each case optionally mono- to trisubstituted by fluorine-substituted C j -Cg-alkyl, C 3 -C 9 -alkenyl, C 1 -C 4 -alkoxy-C 1 -C 3 -alkyl, where appropriate, once to twice by C ] -C 4 -alkyl, C j -C 4 alkoxy or C j -C2
- a and D together are particularly preferably together for optionally mono- to disubstituted C3-C5-alkanediyl in which a methylene group may be replaced by a carbonyl group (but not in the case of the compounds of formula (I-11)), oxygen or sulfur, wherein as substituents C j -C 2 alkyl or Cj-C2 alkoxy come into question or
- a and D are (in the case of the compounds of formula (1-1)) together with the atoms to which they are attached, for one of the groups AD-I to AD-IO:
- a and D together particularly preferably represent C3-C5-alkanediyl which is optionally substituted by one to two not directly adjacent oxygen atoms, containing optionally mono- to tetrasubstituted by Ci-Q-alkyl or Ci-C 3 alkoxy-C r C 2 alkyl substituted Alkylendioxyl group is substituted, whereby a further 5- or 6-ring is formed, or
- a and Q! together are particularly preferably C 3 -C 4 -alkanediyl which is optionally monosubstituted or disubstituted by identical or different substituents and substituted by C 1 -C 2 -alkyl or C 1 -C 2 -alkoxy and which optionally contains the following group: in which
- R ⁇ a and R.16a particularly preferably identical or different methyl or ethyl, or
- Rl6a together are particularly preferably a C2-C4-alkanediyl or C4-alkenediyl radical, which is optionally substituted by methyl or ethyl, or
- B and Q 2 together are particularly preferably -CH 2 -, -CH 2 -CH 2 - -CH 2 -CH 2 -CH 2 -, or -CH 2 -O-CH 2 -, or
- D and Q! together are particularly preferably C3-C4-alkanediyl, or
- Q 1 particularly preferably represents hydrogen, C ⁇ -C 4 alkyl, C ⁇ -C 4 -alkoxy-C j -C 2 alkyl, or optionally methyl- or methoxy-substituted C3-Cg-cycloalkyl in which optionally one methylene group is replaced by oxygen .
- Q 1 particularly preferably represents hydrogen, methyl or ethyl
- ⁇ p, Q-> and Q are particularly preferably independently of one another hydrogen or C1-C3-alkyl
- Q ⁇ particularly preferably represents hydrogen, C j-C4-alkyl, Ci-C4-alkoxy, or represents optionally mono- or disubstituted by methyl or methoxy-substituted, optionally interrupted by an oxygen atom C3-C5 cycloalkyl, or
- Q! and Q.sup.11 are particularly preferably the carbon to which they are attached, optionally substituted by methyl or methoxy C3-C6-cycloalkyl, wherein optionally a methylene group is replaced by oxygen, with the proviso that then A and B particularly preferably independently of one another represent hydrogen or methyl, or
- Q.sup.11 and Q.sup.2 are particularly preferably together with the carbon to which they are bonded, for a saturated C5-Cg ring which is optionally substituted by C.sub.1-C.sub.2-alkyl or C.sub.1-C.sub.2-alkoxy and in which optionally one or two ring members Oxygen or
- A is particularly preferably hydrogen or methyl
- a and Q ⁇ are particularly preferably together with the carbon to which they are attached, an optionally substituted C] -C2 alkyl or Cj-C2 alkoxy saturated C5-Cg ring, in which optionally one ring member is replaced by oxygen or Sulfur is replaced with the proviso that then B, Q ⁇ , Q ⁇ and Q ⁇ are more preferably independently of one another hydrogen or methyl, or
- a and Q.sup.1 are particularly preferably taken together with the carbon atoms to which they are attached, for a saturated or unsaturated C5-Cg ring optionally substituted by C.sub.1-C.sub.2-alkyl or C.sub.1-C.sub.2-alkoxy, with the provisos that B, Q.sup.1, Q.sup.11 and Q.sup.6 are more preferably independently of one another hydrogen or methyl,
- G is particularly preferably hydrogen (a) or one of the groups
- E is a metal ion equivalent or an ammonium ion
- M stands for oxygen or sulfur,! is particularly preferably in each case optionally mono- to trisubstituted by fluorine or
- R ⁇ particularly preferably represents in each case optionally mono- to trisubstituted by fluorine-substituted C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl or C 1 -C 4 -alkoxy-C 2 -C 4 -alkyl,
- R 1 particularly preferably represents C 1 -C -alkyl which is optionally monosubstituted to trisubstituted by fluorine or is optionally monosubstituted by fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro
- R ⁇ is particularly preferably Ci-Cg-alkyl, Cj-Cg-alkoxy, Ci-Cg-alkylamino, di- (C j - Cg-alkyOamino, C 1 -CG-alkylthio, C3-C4-alkenylthio, CSS Cg Cycloalkylthio or each optionally optionally substituted by fluorine, chlorine, bromine, nitro, cyano, C j -C ⁇ -alkoxy, Ci-C3-haloalkoxy, Cj ⁇ -alkylthio, Ci-C3-haloalkylthio, Ci-C3-alkyl or trifluoromethyl substituted Phenyl, phenoxy or phenylthio,
- RS is particularly preferably C 1 -C 6 -alkoxy or C 1 -C 6 -alkylthio
- R 6 particularly preferably represents hydrogen, Cj-Cg alkyl, C3-C6-cycloalkyl, Cj-Cg alkoxy, C3-Cg alkenyl, C j-C6-alkoxy-Ci-C4-alkyl, which is optionally monosubstituted by fluorine , chloro, bromo, trifluoromethyl, C] -C4-alkyl or Cj-C4 alkoxy-substituted phenyl, represents optionally monosubstituted by fluorine, chlorine, bromine, C j -C 4 alkyl, trifluoromethyl or Cj-C4-alkoxy, benzyl,
- R 1 particularly preferably represents C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl or C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl,
- Ro and R ⁇ particularly preferably together represent an optionally methyl or Ethyl substituted C4-C5 alkylene radical in which optionally a methylene group is replaced by oxygen or sulfur.
- halogen is fluorine, chlorine and bromine, in particular fluorine and chlorine.
- W is very particularly preferably hydrogen, chlorine, methyl or ethyl
- X very particularly preferably represents chlorine, methyl, ethyl, methoxy or ethoxy
- Y very particularly preferably represents hydrogen, methyl or chlorine
- Z is most preferably the group
- J 1 and fi very particularly preferably each independently stand for hydrogen or fluorine and P stands for fluorine, chlorine or trifluoromethyl,
- CKE is most preferably one of the groups
- U is very particularly preferably -CH 2 -, -CH 2 -CH 2 -, -O- or
- B is very particularly preferably hydrogen, methyl or ethyl or
- A, B and the carbon atom to which they are attached very particularly preferably represent saturated C 5 -C 9 -cycloalkyl in which optionally a ring member is replaced by nitrogen, oxygen or sulfur and which is optionally mono- or disubstituted by methyl, ethyl, methoxymethyl, Ethoxymethyl, methoxyethyl, ethoxyethyl, trifluoromethyl, methoxy, ethoxy, propoxy, butoxy, methoxyethoxy, ethoxyethoxy, allyloxy, trifluoroethoxy or cyclopropylmethoxy is substituted, the above mentioned radicals also come as N-substituents in question, with the proviso that then Q is very particularly preferably hydrogen or
- A, B and the carbon atom to which they are attached are very particularly preferably C 5 -C 5 -cycloalkyl which is optionally substituted by an alkylidenediyl group which is optionally interrupted by an oxygen atom or by an alkylenedioxy group containing two oxygen atoms which are not directly adjacent to each other, forming a further 5- or 6-membered ring (which may be monosubstituted or disubstituted by methyl) with the proviso that Q.sup.1 is most preferably hydrogen or
- A, B and the carbon atom to which they are attached are most preferably C5-C6 cycloalkyl or C5-C6 cycloalkenyl wherein two substituents together with the carbon atoms to which they are attached are C2-C4 alkanediyl or C2-C4-alkenediyl or butadienediyl, with the proviso that then Q is very particularly preferably hydrogen,
- D very particularly preferably represents hydrogen, represents in each case optionally mono- to trisubstituted by fluorine Cj-C4 alkyl, C3-C4-alkenyl, Ci-C4-alkoxy-C j -C3- alkyl, (cyclopropyl, cyclopentyl or cyclohexyl, or in the case of the compounds of the formulas (1-4)), in each case optionally monosubstituted by fluorine, chlorine, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy or trifluoromethyl, phenyl or pyridyl,
- a and D together are very particularly preferably together C3-C5-alkanediyl which is optionally monosubstituted by methyl or methoxy and in which a carbon atom is optionally replaced by a carbonyl group (but not in the case of the compound of the formula (I-H)), oxygen or sulfur or represents the group AD-I, or
- a and D together are very particularly preferably C 3 -C 5 -alkanediyl which is optionally substituted by an alkylenedioxy group optionally substituted once or twice by C 1 -C 2 -alkyl which is substituted by two oxygen atoms which are not directly adjacent, another 5-ring is formed, or
- a and Q! together are very particularly preferably C3-C4-alkanediyl which is optionally monosubstituted or disubstituted by methyl or methoxy and which may optionally be substituted by methyl or methoxy following group contains: in which R 1 a and R 1 R 6a together are very particularly preferably a C 2 -C 4 -alkanediyl or C 4 -alkendiyl radical, or
- B and Q 2 together are very particularly preferably -CH 2 -CH 2 -CH 2 -, or -CH 2 -O-CH 2 -, or
- D and Q 1 together are very particularly preferably C3-C4-alkanediyl or
- Cy is very particularly preferably hydrogen, methyl, ethyl, propyl, isopropyl, cyclopropyl, cyclopentyl or cyclohexyl,
- Q 1 very particularly preferably represents hydrogen, methyl or ethyl
- Q.sup.1, Q.sup.5 and Q.sup.2 are very particularly preferably each independently of one another hydrogen or methyl
- Q 1 very particularly preferably represents hydrogen, methyl, ethyl, propyl, methoxy or ethoxy, or represents C 3 -C 9 -cycloalkyl optionally interrupted by an oxygen atom, optionally substituted by methyl or methoxy, or
- Cy and CK are most preferably the carbon atom to which they are attached, optionally substituted by methyl or methoxy C5-Cg-cycloalkyl wherein optionally a methylene group is replaced by oxygen, with the proviso that A and B are hydrogen, or
- Q- * and Q ⁇ are most preferably together with the carbon to which they are attached, for a saturated C5-C6 ring, optionally substituted by methyl or methoxy, optionally interrupted by an oxygen atom, with the proviso that A then , B, Cy and Q "are very particularly preferably hydrogen,
- G is very particularly preferably hydrogen (a) or one of the groups
- L is oxygen or sulfur
- M is oxygen or sulfur
- E is a metal ion equivalent or an ammonium ion
- RI very particularly preferably represents in each case optionally monosubstituted by chlorine-substituted Ci-Cg-alkyl, C2-C6 alkenyl, C] -C 2 -alkoxy-C j-alkyl, C ⁇ alkylthio j C j alkyl or optionally cyclopropyl or cyclohexyl which is monosubstituted by fluorine, chlorine, methyl or methoxy,
- R 1 very particularly preferably represents in each case optionally monosubstituted by fluorine C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl or C 1 -C 4 -alkoxy-C 2 -C 3 -alkyl, phenyl or benzyl,
- R 3 very particularly preferably represents C j -C g -alkyl 1.
- W is particularly preferably hydrogen, methyl or ethyl
- X is particularly preferably chlorine, methyl or ethyl
- Y is particularly preferably hydrogen
- Z is particularly preferably OCH 2 -CF 3 in the 3-position
- Z is particularly preferably also OCH 2 -CF 3 in the 4-position
- Z is particularly preferably likewise OCH 2 -CF 3 in the 5-position
- CKE is particularly preferably one of the groups
- B is particularly preferably hydrogen or methyl
- A, B and the carbon atom to which they are attached are particularly preferably saturated C 5 -C 9 -cycloalkyl in which optionally one ring member is replaced by oxygen and which is optionally mono- or disubstituted by methyl, ethyl, methoxymethyl, methoxy, ethoxy, propoxy , Butoxy, trifluoroethoxy, or
- A, B and the carbon atom to which they are attached are very particularly preferably C 9 -cycloalkyl, which is optionally substituted by one not having two directly adjacent ones
- Oxygen-containing alkylenedioxy group is substituted to form another 5- or 6-membered ring which may be monosubstituted or disubstituted by methyl,
- D is particularly preferably hydrogen, or
- a and D together are particularly preferably C3-C5-alkanediyl, wherein optionally one carbon atom is replaced by oxygen or
- a and D together are particularly preferably C3-C5-alkanediyl, which is optionally substituted by one containing two not directly adjacent oxygen atoms optionally mono- to disubstituted by methyl substituted alkylenedioxy group, wherein a further 5- ring is formed, (highlighted A and D together represent C3-C5-alkanediyl which is optionally substituted by an alkylenedioxy group containing two non-directly adjacent oxygen atoms to form another 5-ring), or
- a and Q 1 together are particularly preferably C 3 -Q-alkanediyl
- Q 2 is particularly preferably hydrogen
- G is particularly preferably hydrogen (a) or one of the groups
- RI particularly preferably represents Cj-Cg-Alkvl
- R.2 is particularly preferably Cj-Cg-alkyl.
- Particularly preferred according to the invention are the compounds of the formula (I) which contain a combination of the meanings listed above as being particularly preferred.
- Very particularly preferred according to the invention are the compounds of the formula (I) which contain a combination of the meanings given above as being very particularly preferred.
- Saturated or unsaturated hydrocarbon radicals such as alkyl, alkanediyl or alkenyl can also be straight-chain or branched, as far as possible, also in combination with heteroatoms, for example in alkoxy.
- optionally substituted radicals may be monosubstituted or polysubstituted, with multiple substituents the substituents being the same or different.
- Particularly preferred compounds according to the invention are compounds from the Table 1 mentioned for W, X, Y and Z with the rest combinations for A, B and D mentioned in Tables 2a and 2b in question.
- Further preferred compounds according to the invention are compounds comprising the radical combinations for W, X, Y and Z mentioned in Table 1 with the radical combinations for A and B mentioned in Table 3.
- active compounds are preferred compounds having the radical combinations mentioned in Table 1 for W, X, Y and Z and the radical combinations mentioned in Table 3 for A and B.
- ammonium sulfate as a formulation aid for certain drugs and Applications described (WO 92/16108), but it serves to stabilize the formulation, not to increase the effect.
- the present invention thus relates to the use of ammonium or phosphonium salts to increase the efficacy of plant protection products which contain herbicidal and / or insecticidal and / or acaricidal active haloalkylmethylenoxy-phenyl-substituted ketoenols of the formula (I) as active ingredient.
- the invention also relates to compositions which contain herbicidal and / or acaricidal and / or insecticidally active haloalkylmethylenoxyphenyl-substituted ketoenols of the formula (I) and the activity-enhancing ammonium or phosphonium salts, both formulated active ingredients and ready-to-use agents (spray liquors).
- the invention further relates to the use of these agents for controlling noxious insects and / or spider mites and / or undesired plant growth.
- the compounds of the formula (I) have a broad insecticidal and / or acaricidal and / or herbicidal action, but the action and / or plant tolerance leaves something to be desired in detail.
- the active compounds can be used in the compositions according to the invention in a wide concentration range.
- concentration of the active ingredients in the formulation is usually 0.1-50 wt .-%.
- Ammonium and phosphonium salts which according to the invention increase the action of crop protection agents containing fatty acid biosynthesis inhibitors are defined by formula (EI ')
- D is nitrogen or phosphorus, D is preferably nitrogen,
- R 26 , R 27 , R 28 and R 29 independently of one another are hydrogen or in each case optionally substituted C 1 -C 6 -alkyl or mono- or polyunsaturated, optionally substituted C 1 -C 6 -alkylene, where the substituents are selected from halogen, nitro and cyano can,
- R 26 , R 27 , R 28 and R 29 preferably independently of one another represent hydrogen or in each case optionally substituted C 1 -C 4 -alkyl, where the substituents can be selected from halogen, nitro and cyano,
- R 26 , R 27 , R 28 and R 29 particularly preferably independently of one another represent hydrogen
- R 26 , R 27 , R 28 and R 29 most preferably represent hydrogen
- n 1, 2, 3 or 4
- n is preferably 1 or 2
- R 3 is an inorganic or organic anion
- R 30 is preferably hydrogencarbonate, tetraborate, fluoride, bromide, iodide, chloride, monohydrogenphosphate, dihydrogenphosphate, hydrogensulphate, tartrate, sulphate, nitrate, thiosulphate, thiocyanate, formate, lactate, acetate, propionate, butyrate, pentanoate or oxalate,
- R 30 particularly preferably represents lactate, sulfate, nitrate, thiosulphate, thiocyanate, oxalate or formate,
- R 30 very particularly preferably represents sulfate.
- Penetration promoter means that any compound which acts as a penetration promoter in the test for cuticle penetration (Baur et al., 1997, Pesticide Science 51, 131-152) is suitable.
- the ammonium and phosphonium salts of the formula (HI ') can be used in a broad concentration range to increase the effect of pesticides Ketoenols are used.
- the ammonium or phosphonium salts in the ready-to-use crop protection agent are used in a concentration of 0.5 to 80 mmol / l, preferably 0.75 to 37.5 mmol / l, particularly preferably 1.5 to 25 mmol / l.
- the ammonium and / or phosphonium salt concentration in the formulation is selected to be in the specified general, preferred or more preferred ranges after dilution of the formulation to the desired drug concentration.
- the concentration of the salt in the formulation is usually 1-50 wt .-%.
- a penetration promoter is added to the crop protection agents to increase the effect. It can be described as completely surprising that even in these cases an even greater increase in activity can be observed.
- the present invention thus also relates to the use of a combination of penetrants and ammonium and / or phosphonium salts to increase the efficacy of plant protection products containing insecticidal and / or acaricidal and / or herbicidally active haloalkylmethylenoxy-phenyl-substituted ketoenols of the formula (I) as active ingredient .
- the invention also relates to compositions which contain herbicidal and / or acaricidal and / or insecticidally active haloalkylmethyleneoxy-phenyl-substituted ketoenols of the formula (I), penetrants and ammonium and / or phosphonium salts, both formulated active ingredients and ready-to-use agents (spray liquors ).
- the invention further relates to the use of these agents for controlling noxious insects and / or spider mites and / or undesired plant growth.
- Suitable penetration promoters in the present context are all those substances which are usually used to improve the penetration of agrochemical active substances into plants.
- Penetration promoters are defined in this context by the fact that they can penetrate from the aqueous spray mixture and / or from the spray coating in the cuticle of the plant and thereby increase the material mobility (mobility) of active ingredients in the cuticle.
- the method described in the literature can be used to determine this property.
- Suitable penetration promoters are, for example, alkanol alkoxylates.
- Penetration promoters according to the invention are alkanol alkoxylates of the formula (Fv ") in which R represents straight-chain or branched alkyl having 4 to 20 carbon atoms,
- R 1 is hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl or n-hexyl,
- AO stands for an ethylene oxide radical, a propylene oxide radical, a butylene oxide radical or mixtures of ethylene oxide and propylene oxide radicals or butylene oxide radicals and
- v stands for numbers from 2 to 30.
- a preferred group of penetration enhancers are alkanol alkoxylates of the formula
- n stands for numbers from 2 to 20.
- Another preferred group of penetration enhancers are alkanol alkoxylates of the formula
- EO stands for -CH 2 -CH 2 -O-
- Another preferred group of penetration promoters are alkanol alkoxylates of the formula
- EO is -CH 2 -CH 2 -O-
- PO stands for r is a number from 1 to 10 and s is a number from 1 to 10.
- Another preferred group of penetration promoters are alkanol alkoxylates of the formula RO - (- EO-) p - (- BO-) q -R '(IV'-d) in which
- R and R have the meanings given above, EO is -CH 2 -CH 2 -O-,
- BO stands for p stands for numbers from 1 to 10 and q stands for numbers from 1 to 10.
- Another preferred group of penetration promoters are alkanol alkoxylates of the formula RO - (--BO-) r - (- EO-) s -R '(IV'-e) in which
- EO stands for -CH 2 -CH 2 -O-
- s stands for numbers from 1 to 10.
- Another preferred group of penetration promoters are alkanol alkoxylates of the formula
- u stands for numbers from 6 to 17.
- R is preferably butyl, i-butyl, n-pentyl, i-pentyl, neo-pentyl, n-hexyl, i-hexyl, n-octyl, i-octyl, 2-ethyl-hexyl, nonyl, i-nonyl, decyl, n Dodecyl, i-dodecyl, lauryl,
- alkanol alkoxylate of the formula (IV-c) is 2-ethyl-hexyl alkoxylate of the formula
- EO stands for -CH 2 -CH 2 -O-
- PO stands for
- the numbers 8 and 6 represent average values called.
- EO stands for -CH 2 -CH 2 -O-
- the numbers 10, 6 and 2 represent average values called.
- alkanol alkoxylates of the formula (IV ⁇ -f) are compounds of this formula in which
- alkanol alkoxylate of the formula (FV'-f-1) very particular preference is given to alkanol alkoxylate of the formula (FV'-f-1)
- u stands for the average 8.4.
- the alkanol alkoxylates are generally defined by the above formulas. These substances are mixtures of substances of the specified type with different chain lengths. For the indices, therefore, average values are calculated, which can also differ from whole numbers.
- the alkanol alkoxylates of the formulas given are known and are partly available commercially or can be prepared by known methods (compare WO 98/35 553, WO 00/35 278 and EP-A 0 681 865).
- suitable penetration promoters are substances which promote the availability of the compounds of the formula (I) in the spray coating. These include, for example, mineral or vegetable oils. As oils are all commonly used in agrochemical means mineral or vegetable - optionally modified
- oils in question examples include sunflower oil, rapeseed oil, olive oil, castor oil, rapeseed oil,
- the concentration of penetration promoter can be varied within a wide range in the agents according to the invention.
- a formulated crop protection agent it is generally from 1 to 95% by weight, preferably from 1 to 55% by weight, more preferably from 15 to 40% by weight.
- the concentration is generally between 0.1 and 10 g / l, preferably between 0.5 and 5 g / l.
- Plant protection agents according to the invention may also contain further components, for example surfactants or dispersing aids or emulsifiers.
- Suitable nonionic surfactants or dispersing agents are all substances of this type which can usually be used in agrochemical compositions. Preference is given to polyethylene oxide-polypropylene oxide block copolymers, polyethylene glycol ethers of linear alcohols, reaction products of fatty acids with ethylene oxide and / or propylene oxide, furthermore polyvinyl alcohol, polyvinylpyrrolidone, copolymers of polyvinyl alcohol and polyvinylpyrrolidone and copolymers of (meth) acrylic acid and (meth) acrylic esters , furthermore alkyl ethoxylates and alkylaryl ethoxylates, which may optionally be phosphated and optionally neutralized with bases, wherein sorbitol ethoxylates may be mentioned by way of example, and polyoxyalkyleneamine derivatives.
- Suitable anionic surfactants are all substances of this type conventionally usable in agrochemical compositions. Preference is given to alkali metal and alkaline earth metal salts of alkyl sulfonic acids or alkylaryl sulfonic acids.
- a further preferred group of anionic surfactants or dispersants are salts of polystyrenesulfonic acids which are sparingly soluble in vegetable oil, salts of polyvinylsulfonic acids, salts of naphthalenesulfonic acid-formaldehyde condensation products, salts of condensates. sation products of naphthalenesulfonic acid, phenolsulfonic acid and formaldehyde and salts of lignosulfonic acid.
- Suitable additives which may be present in the formulations according to the invention are emulsifiers, foam-inhibiting agents, preservatives, antioxidants, dyes and inert fillers.
- Preferred emulsifiers are ethoxylated nonylphenols, reaction products of alkylphenols with ethylene oxide and / or propylene oxide, ethoxylated arylalkylphenols, furthermore ethoxylated and propoxylated arylalkylphenols, and sulfated or phosphated arylalkyl ethoxylates or ethoxy-propoxylates, sorbitan derivatives such as polyethylene oxide sorbitan fatty acid esters and sorbitan Fatty acid esters, may be mentioned as examples.
- reaction scheme (2,6-dimethyl-4-trifluoroethoxyphenyl) - 5,5-pentamethylene-pyrrolidine-2,4-dione and methanesulfonyl chloride as the starting material, the reaction can be represented by the following reaction scheme become:
- reaction course can be represented by the following reaction scheme:
- A, B, D, WX, Y, Z and R 8 have the meanings given above,
- acylamino acid esters of the formula (D) are obtained, for example, if amino acid derivatives of the formula (XXVII) are obtained.
- W, X, Y and Z have the meanings given above, and
- carboxylic acid activating reagents such as carbonyldiimidazole, carbonyldiimides (such as dicyclohexylcarbonediimide), phosphorylation reagents (e.g.
- halogenating agent e.g. Is the leaving group introduced with thionyl chloride, oxalyl chloride, phosgene or chloroformate,
- A, B, D, W, X 5 Y and Z have the meanings given above are new.
- W, X, Y and Z have the meanings given above, and
- the compounds of formula (XXVIII) are new. They can be prepared by processes which are known in principle (see, for example, H. Henecka, Houben-Weyl, Methoden der Organischen Chemie, Vol. 8, pp. 467-469 (1952)) WO 97/02243, WO 99/43699 or are disclosed in US Pat Reagents generated above in situ.
- W, X, Y and Z are as defined above,
- halogenating agents for example thionyl chloride, thionyl bromide, oxalyl chloride, phosgene, phosphorus trichloride, phosphorus tribromide or phosphorus tachloride), Phosphonyl mecanicsreagenzien such as (eg POCl3, BOP-Cl), carbonyldiimidazole, carbonyldiimides (eg Dicyclohexylcarbonyldiimid) optionally in the presence of a diluent (eg, optionally chlorinated alipha - Table or aromatic hydrocarbons such as toluene or methylene chloride or ethers, for example tetrahydrofuran, dioxane, methyl tert-butyl ether) at temperatures from -20 0 C to 150 ° C, preferably from -10 0 C to 100 0 C, is reacted.
- a diluent eg, optionally
- the substituted cyclic aminocarboxylic acids of the formula (XXX) in which A and B form a ring are generally obtainable by the Bucherer-Bergs synthesis or by the Strecker synthesis and in each case arise in different isomeric forms.
- ß isomers
- the radicals R and the carboxyl group are equatorial
- the isomers im hereinafter referred to as ⁇ for the sake of simplicity
- A, B, D, W, X, Y, Z and R 8 have the meanings given above,
- W, X, Y, Z and ⁇ fl have the meanings given above,
- A, B, D, W, X, Y and Z have the meanings given above,
- A, B, W, X, Y, Z and R 8 have the meanings given above are new. They can be prepared by methods known in principle.
- A, B and R 8 have the meanings given above and
- Hal is chlorine or bromine
- W, X, Y, Z and R 8 have the abovementioned meaning
- W, X, Y, Z and R 8 have the abovementioned meaning
- R 8 , W, X and Y have the abovementioned meaning
- haloalkyl alcohols e.g. Trifluoroethanol in the presence of a base and optionally in the presence of a copper salt (preferably Cu-I-J) is reacted.
- phenylacetic acid esters of the formula (XXXV-a) are in principle, for example, from Publications WO 96/35 664, WO 97/02243, WO 97/01535, WO 98/05638 and DE-A-10 301 804 are known and can be prepared by the processes described therein.
- A, B, V, W, X, Y, Z and R 8 have the meanings given above are new.
- Hal is halogen (especially chlorine or bromine), acylated in the presence of strong bases (see eg MS Chambers, EJ Thomas, DJ Williams, J. Chem. Soc. Chem. Commun., (1987), 1228).
- benzylthio-carboxylic acid halides of the formula (XXXVI) are known in some cases and / or can be prepared by known processes (J. Antibiotics (1983), 26, 1589).
- halocarbonyl ketones of the formula (VI) required as starting materials in the above processes (D), (E) and (H- ⁇ ) are novel. They can be prepared by methods known in principle (cf., for example, Org., Prep., Proced. Int., 7, (4), 155-158, 1975, and DE 1 945 703). Thus, for example, the compounds of the formula (VI)
- W, X, Y and Z have the meanings given above, and
- Hal is chlorine or bromine
- W, X, Y and Z are as defined above,
- W, X, Y and Z are as defined above,
- R 8 has the meaning given above
- A, D and R 8 have the meanings given above, are commercially available, commonly known or accessible by known methods compounds.
- A, B, Q, Q 2, W, X, Y, Z and R 8 have the abovementioned meaning
- the 5-aryl-4-ketocarboxylic esters of the formula (VIII) are obtained, for example, by reacting 5-aryl-4-ketocarboxylic acids of the formula (XXXVIII)
- W, X, Y, Z, A, B, Q 1 and Q 2 are as defined above,
- A, B, Q 1 , Q 2 , W, X, Y and Z are as defined above,
- the 5-aryl-4-ketocarboxylic acids of the formula (XXXVIII) are obtained, for example, by reacting 2-phenyl-3-oxo-adipic esters of the formula (XXXEX)
- A, B, Ql, Q 2 , W, X, Y and Z are as defined above and
- R 8 and R 8 ' are alkyl (in particular C 1 -C 6 -alkyl) and when using the compound of the formula (XLI-a) R 8 is hydrogen,
- A, B, Q 1, Q 2 and R 8 have the abovementioned meaning and
- Hal is chlorine or bromine
- the compounds of the formulas (XL) and (XLI-a) are partially known compounds of organic chemistry and / or can be prepared in a simple manner by methods known in principle.
- A, B, Q 5 , Q 6 , U, W, X, Y, Z and R 8 are as defined above,
- 6-aryl-5-ketocarboxylic acid esters of the formula (DC) are obtained, for example, by reacting 6-aryl-5-ketocarboxylic acids of the formula (XLII)
- U, W, X, Y and Z are as defined above,
Abstract
Description
Claims
Priority Applications (11)
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BRPI1008949-7A BRPI1008949B1 (pt) | 2009-03-11 | 2010-03-05 | Cetoenóis haloalquilmetilenóxi-fenil-substituídos e seu uso, composição, seu uso e seu método de produção, métodos para combate de pestes animais e/ou crescimento de plantas indesejadas |
AU2010223535A AU2010223535B2 (en) | 2009-03-11 | 2010-03-05 | Halogenalkylmethylenoxy-phenyl-substituted ketoenols |
EP10708924.5A EP2406216B1 (de) | 2009-03-11 | 2010-03-05 | Halogenalkylmethylenoxy-phenyl-substituierte ketoenole |
MX2011009188A MX2011009188A (es) | 2009-03-11 | 2010-03-05 | Cetoenoles sustituidos con haloalquilmetilenoxi-fenilo. |
MX2013011965A MX338802B (es) | 2009-03-11 | 2010-03-05 | Cetoenoles sustituidos con haloalquilmetilenoxi-fenilo. |
KR1020117023789A KR101703633B1 (ko) | 2009-03-11 | 2010-03-05 | 할로겐알킬메틸렌옥시페닐-치환된 케토에놀 |
CN201080011864.3A CN102348684B (zh) | 2009-03-11 | 2010-03-05 | 被卤代烷基亚甲基氧基苯基取代的酮烯醇 |
CA2754847A CA2754847C (en) | 2009-03-11 | 2010-03-05 | Halogenalkylmethylenoxy-phenyl-substituted ketoenols |
JP2011553331A JP5840955B2 (ja) | 2009-03-11 | 2010-03-05 | ハロゲンアルキルメチレンオキシフェニル置換ケトエノール類 |
ES10708924.5T ES2632567T3 (es) | 2009-03-11 | 2010-03-05 | Cetoenoles sustituidos con haloalquilmetilenoxi-fenilo |
EA201190190A EA024266B1 (ru) | 2009-03-11 | 2010-03-05 | Кетоенолы, замещенные галоидалкилметиленоксифенилом, и их применение |
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US (2) | US8518985B2 (de) |
EP (2) | EP2406216B1 (de) |
JP (1) | JP5840955B2 (de) |
KR (1) | KR101703633B1 (de) |
CN (2) | CN103641709B (de) |
AR (1) | AR075848A1 (de) |
AU (1) | AU2010223535B2 (de) |
BR (1) | BRPI1008949B1 (de) |
CA (1) | CA2754847C (de) |
EA (1) | EA024266B1 (de) |
ES (1) | ES2632567T3 (de) |
HU (1) | HUE035166T2 (de) |
MX (2) | MX2011009188A (de) |
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- 2010-03-05 WO PCT/EP2010/001392 patent/WO2010102758A2/de active Application Filing
- 2010-03-05 MX MX2011009188A patent/MX2011009188A/es active IP Right Grant
- 2010-03-05 KR KR1020117023789A patent/KR101703633B1/ko active IP Right Grant
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- 2010-03-05 MX MX2013011965A patent/MX338802B/es unknown
- 2010-03-05 EP EP16193742.0A patent/EP3153503A1/de not_active Withdrawn
- 2010-03-05 AU AU2010223535A patent/AU2010223535B2/en not_active Ceased
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BRPI1008949A8 (pt) | 2016-05-03 |
MX2011009188A (es) | 2011-09-26 |
US9045390B2 (en) | 2015-06-02 |
CN103641709B (zh) | 2017-08-25 |
AU2010223535A1 (en) | 2011-09-22 |
EP3153503A1 (de) | 2017-04-12 |
US20140031577A1 (en) | 2014-01-30 |
KR20110132591A (ko) | 2011-12-08 |
AU2010223535B2 (en) | 2015-09-10 |
ES2632567T3 (es) | 2017-09-14 |
EP2406216B1 (de) | 2017-04-19 |
WO2010102758A3 (de) | 2011-01-20 |
EA201190190A1 (ru) | 2012-02-28 |
CA2754847A1 (en) | 2010-09-16 |
BRPI1008949A2 (pt) | 2015-09-01 |
AR075848A1 (es) | 2011-05-04 |
EA024266B1 (ru) | 2016-09-30 |
US8518985B2 (en) | 2013-08-27 |
CN102348684B (zh) | 2014-11-12 |
EP2406216A2 (de) | 2012-01-18 |
PL2406216T3 (pl) | 2017-09-29 |
JP2012520242A (ja) | 2012-09-06 |
CA2754847C (en) | 2017-07-11 |
CN103641709A (zh) | 2014-03-19 |
KR101703633B1 (ko) | 2017-02-07 |
MX338802B (es) | 2016-05-02 |
CN102348684A (zh) | 2012-02-08 |
HUE035166T2 (en) | 2018-05-02 |
JP5840955B2 (ja) | 2016-01-06 |
US20100311593A1 (en) | 2010-12-09 |
BRPI1008949B1 (pt) | 2018-07-10 |
US20140213813A9 (en) | 2014-07-31 |
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