Classifications

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  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
  • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
  • C07D213/53—Nitrogen atoms
• • 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
  • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
  • A01N35/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen
  • A01N35/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen containing a carbon-to-nitrogen double bond
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  • 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
  • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
  • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
  • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
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  • 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
• • 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
  • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
• • 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
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
• • 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
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K35/00—Medicinal preparations containing materials or reaction products thereof with undetermined constitution
  • A61K35/02—Medicinal preparations containing materials or reaction products thereof with undetermined constitution from inanimate materials
  • A61K35/10—Peat; Amber; Turf; Humus
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  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
  • C07C251/32—Oximes
  • C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
  • C07C251/48—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a six-membered aromatic ring
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  • C07C251/32—Oximes
  • C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
  • C07C251/52—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by halogen atoms or by nitro or nitroso groups
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  • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
  • C07C251/32—Oximes
  • C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
  • C07C251/54—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by singly-bound oxygen atoms
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  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
  • C07D213/61—Halogen atoms or nitro radicals
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  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
  • C07D213/62—Oxygen or sulfur atoms
  • C07D213/63—One oxygen atom
  • C07D213/64—One oxygen atom attached in position 2 or 6
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  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
  • C07D213/62—Oxygen or sulfur atoms
  • C07D213/63—One oxygen atom
  • C07D213/64—One oxygen atom attached in position 2 or 6
  • C07D213/643—2-Phenoxypyridines; Derivatives thereof
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  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
  • C07D213/62—Oxygen or sulfur atoms
  • C07D213/63—One oxygen atom
  • C07D213/65—One oxygen atom attached in position 3 or 5
• • C—CHEMISTRY; METALLURGY
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  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
  • C07D213/72—Nitrogen atoms
  • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
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  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
  • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
  • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
  • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
  • C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
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  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
  • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
  • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
  • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
  • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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  • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
  • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
  • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

• the invention relates to new substituted (hetero) aryl alkyl ketone oxime O ethers, processes for their preparation, compositions containing them and their use for controlling pests, in particular insects, acarina and
• Oxime ethers and their use as pesticides are e.g. T. already known [G. Holan et al., Recent Advances in the Chemistry of Insect Control II, pp. 114 ff. Cambridge 1990; T.G. Cullen et al., ACS Symp. Ser. 335 (1987) 173; M.J. Bull et al., Pestic. Be. 11 (1980) 349; WO-A-84/01772].
• Heteroaromatic oxime ethers with insecticidal properties are known from EP-A-4754 and EP-A-24888. However, some of them are insufficiently effective.
• New oxime O ethers with advantageous pesticidal, in particular insecticidal, acaricidal and / or nematicidal properties have been found.
• the invention therefore relates to compounds of the formula I and their salts,
• Ar 1 and Ar 2 are the same or different
• -ON CR ' 2 , in which R' represents identical or different radicals from the series hydrogen, (C 1 -C 6 ) alkyl, (C 3 -C 8 ) cycloalkyl and (C 6 -C 12 ) - Aryl stands,
• Halogen are replaced, the number of halogen atoms ⁇ . Is 4; the aryl and heteroaryl defined under L a) and b) can also be partially hydrogenated and one or two CH 2 groups can be replaced by CO therein; III. with the proviso that
• Ar 2 as defined under I. a) or b) but does not mean 4-fluoro-3-phenoxyphenyl, 3-phenoxyphenyl, pentafluorophenyl or 2,6-dihalophenyl; c) if R is (C 2 -C 6 ) -alkyl or is as defined under II. b) -f) and if Ar 1 is as defined under I. a), or as aryl as defined under lb) or as under lb ) 1st-20th or 24.-45.) defined heteroaryl means Ar 2 as defined under I. a and b), but not for
• X is O or S
• R 10 , R 11 and R 12 are the same or different and are hydrogen
• R 13 is hydrogen, fluorine or methyl
• R 6 is hydrogen, fluorine or alkyl
• R 8 is alkenyl or haloalkenyl; d) if R is (C 2 -C 6 ) -alkyl or is as defined under II. b) -f) and if Ar 1 is under I. b) 21.-23. defined heteroaryl means Ar 2 can also have the meaning defined under I. a and b); e) if R is (C 2 -C 6 ) -alkyl or is as defined under II. b) -f) and if Ar 1 is heteroaryl as defined under I. a) or b), Ar 2 also means pentafluorophenyl or
• R 13 and o are as defined above; f) if R is as defined under II. e) substituted (C 2 -C 6 ) alkyl, (C 2 -C 6 ) alkenyl or (C 2 -C 6 ) alkynyl and if Ar 1 under I. a ) or b) defined aryl, Ar 2 also means
• R 13 and o are as defined above; and g) if R is (C 2 -C 6 ) -alkyl or is as defined under II. b) -f) and if Ar 1 is as defined under I. b) 21. substituted (C 6 -C 12 ) -aryl means Ar 2 can also mean pentafluorophenyl.
• Alkyl, alkenyl and alkynyl can be straight-chain or branched. This also applies to residues derived therefrom, such as alkoxy, alkylmercapto, haloalkyl and arylalkyl.
• Haloalkyl, haloalkenyl and haloalkynyl are understood to mean alkyl, alkenyl or alkynyl, in which one, more or all hydrogen atoms have been replaced by halogen. The same applies to residues derived therefrom, such as haloalkoxy,
• Haloalkenyloxy or haloalkynyloxy
• Halogen means fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine.
• (C 6 -C 12 ) aryl preferably represents phenyl and radicals derived therefrom, such as naphthyl, biphenyl and indanyl.
• a heteroaryl radical with up to 10 carbon atoms is a preferably mono- or bicyclic aryl radical in which at least one CH is replaced by N and / or wherein at least two adjacent CH groups are replaced by NH, O and / or S.
• Examples of such radicals are thienyl, benzothienyl, furyl, benzofuryl, pyrrolyl, imidazolyl, pyrazolyl, pyrodyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, oxazolyl, isoxazolyl, thiazolyl and isothiazolyl.
• the invention also relates to their salts, in particular their acid addition salts.
• Acids that can be used for salt formation are inorganic acids such as
• Hydrochloric acid hydrobromic acid, nitric acid, sulfuric acid, phosphoric acid or organic acids such as formic acid, acetic acid, propionic acid, malonic acid, oxalic acid, fumaric acid, adipic acid, stearic acid, oleic acid, methanesulfonic acid, benzenesulfonic acid or toluenesulfonic acid.
• X represents O, S or NR 3 and
• (C 2 -C 6 ) alkynyl preferably -CH 2 -C ⁇ CH
• (C 3 -C 8 ) cycloalkyl optionally substituted with up to 6 identical or different radicals from the halogen and (C 1 -C 4 ) alkyl group, (C 1 -C 6 ) haloalkyl,
• Heteroaryloxycarbonyl having up to 10 C atoms in particular those compounds of the formula I in which
• Ar 1 is a radical of the formula
• p is an integer from 0 to 5
• R 1 is the same or different
• (C 6 -C 12 ) aryl optionally substituted up to three times with identical or different radicals from the series halogen, (C 1 -C 6 ) alkyl, (C 1 -C 6 ) alkoxy, (C 1 -C 6 ) -haloalkyl and (C 1 -C 6 ) -haloalkoxy,
• Heteroaryl- (C 1 -C 4 ) -alkyl having up to 10 C atoms in the heteroaryl part and optionally substituted there as aryl mentioned above,
• R 1 is in particular (C 1 -C 6 ) haloalkoxy, such as OCHF 2 , OCF 3 ,
• R 1 radicals mentioned as preferred are preferably in the 4-position of the phenyl radical, in the corresponding position of a heteroaromatic six-membered ring or in an analogous position in a heterocyclic five-membered ring (see below), the following Ar 1 radicals being preferred:
• R preferably denotes (C 1 -C 6 ) -alkyl or (C 3 -C 8 ) -cycloalkyl, which can in each case be partially or completely substituted by halogen, in particular (C 1 -C 6 ) -alkyl, which can be substituted with up to 3 Fluorine can be substituted, such as CF 3 , CF 2 H, or isopropyl or cyclopropyl.
• Ar 2 preferably means
• A, B and C are the same and different and denote N, CH or C-Hal,
• R 9 denotes hydrogen or as defined as R 1 ,
• R 3 is as defined above
• R 10 , R 11 and R 12 are as defined above, preferably CH 3 , CF 3 , CN,
• R 13 denotes hydrogen, fluorine or methyl
• O 0, 1 or 2
• R 6 denotes hydrogen, fluorine or (C 1 -C 6 ) alkyl
• CH 2 -CH CH 2 or CH 2 -C ⁇ CH means and
• R 8 is (C 2 -C 6 ) alkenyl or (C 2 -C 6 ) haloalkenyl.
• Ar 2 is as defined above under A., preference is given to compounds in which A, B and C are not all N at the same time, in particular those in which only one of the groups is A, B or CN. Are preferred
• R 9 is (C 1 -C 6 ) alkyl, in particular methyl, (C 1 -C 6 ) alkoxy, (C 1 -C 6 ) haloalkoxy or (C 1 -C 6 ) haloalkyl.
• X is NR 3 , O or S, Q 'is O or CH 2 and R 11 and R 12 are as defined above.
• Ar 1 is optionally substituted Heteroaryl and R mean trifluoromethyl or wherein Ar 1 is optionally substituted aryl or heteroaryl, Ar 2 is as defined above under D. or E. and R is trifluoromethyl.
• the oxime ethers of the formula I can occur in two isomeric forms: the “syn” and the “anti” form.
• “syn” regardless of the substituent R, denotes the oxime ether in which the oxime oxygen is syn to the aromatic or heteroaromatic Ar 1 .
• the invention relates to both the syn and anti forms and mixtures of both forms.
• compounds of the formula I can have one or more
• Racemates can be converted into the enantiomers by customary methods
• the invention also relates to a process for the preparation of compounds of the formula I, which is characterized in that a) a compound of formula II
• Ar 1 and R are defined in formula I and M is hydrogen or a
• alkali metal atom means reacting with a compound of the formula III in the presence of a suitable base
• the reaction is carried out in the presence of a suitable base such as tert.
• a suitable base such as tert.
• Alkali metal bicarbonates, alkali metal carbonates in a suitable solvent preferably from the group ether (diethyl ether, THF, dimethoxyethane, dioxane etc.), aromatic and non-aromatic, also halogenated
• Hydrocarbons toluene, heptane, chlorobenzene, etc.
• aprotic, dipolar solvents such as DMF, DMSO, acetonitrile, acetone, N-methylpyrrolidone
• Suitable leaving groups X are halogen (with the exception of fluorine), OSO 2 CH 3 , OSO 2 CF 3 , p-toluenesulfonyloxy or quaternary ammonium salts etc.
• the oxime ethers according to the invention can also by condensation of a hydroxylamine-O-alkyl-aryl 2 ether (salt) with the respective ketone, possibly in
• Alkali metal carboxylates tert. are particularly suitable as bases.
• Amines are particularly suitable as bases.
• Alkali metal hydroxides, alkali metal carbonates and bicarbonates as
• Solvents (also in the form of mixtures), preferably alcohols,
• Hydrocarbons, halogenated and non-halogenated (also aromatic) Hydrocarbons, ethers Hydrocarbons, halogenated and non-halogenated (also aromatic) Hydrocarbons, ethers.
• the hydroxylamine O-ethers can be prepared according to the literature specification (Kaztreiner et al., Acta Chem. Hung. 80 (1975) 167).
• Hydroxylammonium salt such as hydroxylamine hydrochloride at temperatures between - 20 and + 150 ° C in a suitable solvent from the group of alcohols, (halogenated) aromatic and non-aromatic hydrocarbons, ethers (THF, dioxane, diethyl ether, dimethoxyethane), preferably water, possibly with the addition of a suitable base as defined under (b) (see also Houben-Weyl; Methods of Organic Chemistry, Volume 10/4 pp. 55 ff, 352 ff; Volume E 14b Part 1, pp. 287 ff, 307 ff, 367 ff and RL Salvador et al., J. Med. Chem. 15 (1972) 646).
• a suitable solvent from the group of alcohols, (halogenated) aromatic and non-aromatic hydrocarbons, ethers (THF, dioxane, diethyl ether, dimethoxyethane), preferably water, possibly with the addition of
• the oximes or mixtures of the isomeric oximes can be prepared using (Lewis) acids such as boron trifluoride etherate, titanium tetrachloride, HCl and others. can be converted into the thermodynamically more stable form according to the literature specification (US Patent 4158015).
• the trifluoromethyl ketones can be synthesized in various ways, e.g. described in the literature (J.-P. Begue et al., Tetrahedron 47 (1991) 3207), but preferably via
• Ar 1 aromatic, heteroaromatic
• the active ingredients are suitable for good plant tolerance and cheaper
• Warmblood toxicity for controlling animal pests in particular insects, arachnids, helminths, nematodes and molluscs, very particularly preferably for controlling insects and arachnids, which in the
• Acarina e.g. Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rh ⁇ picephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spptes, ., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Eotetranychus spp., Oligonychus spp., Eutetranychus spp.
• Acarina e.g. Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis,
• Tysanura e.g. Lepisma saccharina.
• Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci.
• Trialeurodes vaporariorum Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi,
• Empoasca spp. Euscelus bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla 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, Costimallontra pursuits.
• Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
• hypoderma spp. Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa.
• Ancylostoma, Ascaris and Heterakis as well as Fasciola and plant and animal-damaging nematodes e.g. B. those of the genera Meloidogyne, Heterodera, Ditylenchus, Aphelenchoides, Radopholus, Globodera, Pratylenchus, Longidorus and Xiphinema.
• the invention also relates to compositions which contain the compounds of the formula I in addition to suitable formulation auxiliaries.
• the agents according to the invention generally contain the active ingredients of the formula I in an amount of 1 to 95% by weight.
• emulsifiable concentrates EC
• SC aqueous solutions
• SC emulsions
• sprayable solutions oil or water-based dispersions
• SC suspoemulsions
• DP dusts
• mordants granules in the form of micro, spray, elevator - and adsorption granules
• WG water-dispersible granules
• ULV formulations microcapsules, waxes and baits.
• the necessary formulation aids such as inert materials, surfactants, solvents and other additives are also known and are, for example described in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell NJ; HvOlphen, "Introduction to Clay Colloid
• combinations with other pesticidally active substances, fertilizers and / or growth regulators can also be prepared, e.g. B. in the form of a finished formulation or as a tank mix.
• Spray powders are preparations which are uniformly dispersible in water and which, in addition to the active substance, are also a wetting agent, in addition to a diluent or inert substance.
• Alkylphenols, polyoxethylated fatty alcohols, alkyl or alkylphenol sulfonates and dispersants e.g. B. sodium lignosulfonate, 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, dibutylnaphthalene-sulfonic acid sodium or oleylmethyl tauric acid sodium.
• Emulsifiable concentrates are made by dissolving the active ingredient in an organic solvent, e.g. Butanol, cyclohexanone, D ⁇ methylformamid, xylene or higher-boiling aromatics or hydrocarbons with the addition of one or more emulsifiers. The following can be used as emulsifiers:
• Alkylarylsulfonic acid calcium salts such as Ca-dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers,
• Dusts are obtained by grinding the active ingredient with finely divided solid substances, for example talc, natural clays such as kaolin, bentonite, pyrophillite or diatomaceous earth.
• Granules can either be produced by spraying the active ingredient onto adsorbable, granulated inert material or by Application of active ingredient concentrates to the surface of by means of adhesives, for example polyvinyl alcohol, polyacrylic acid sodium or mineral oils
• Carriers such as sand, kaolinite or granulated inert material. Suitable active ingredients can also be granulated in the manner customary for the production of fertilizer granules, if desired in a mixture with fertilizers.
• the active substance concentration in wettable powders is e.g. about 10 to 90 wt .-%, the rest of 100 wt .-% consists of conventional formulation components. In the case of emulsifiable concentrates, the active substance concentration can be approximately 5 to 80% by weight. Dust-like formulations usually contain 5 to 20 wt .-% of active ingredient, sprayable solutions about 2 to 20 wt .-%. In the case of granules, the active ingredient content depends in part on whether the active compound is in liquid or solid form and which granulation aids, fillers, etc. are used.
• the active ingredient formulations mentioned may contain the customary adhesives, wetting agents, dispersants, emulsifiers, penetrants, solvents, fillers or carriers.
• the concentrates which are commercially available, are diluted in the customary manner, e.g. in the case of wettable powders, emulsifiable concentrates, dispersions and in some cases also in the case of microgranules by means of water, dusty and granulated preparations and sprayable solutions are usually no longer diluted with further inert substances before use.
• the required application rate varies. It can fluctuate within wide limits, e.g. between 0.005 and 10.0 kg / ha or more of active substance, but is preferably between 0.01 and 5 kg / ha.
• the active compounds according to the invention can be used in their commercially available formulations and in the use forms prepared from these formulations
• Herbicides are present.
• the pesticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, formamidines, tin compounds
• Fensulfothion, Fenthion, Fonofos Formothion, Heptenophos, Isazophos, Isothioate, Isoxathion, Malathion, Methacrifos, Methamidophos, Methidathion, Salithion, Mevinphos, Monocrotophos, Naled, Omethoate,
• Isoprocarb methomyl, 5-methyl-m-cu-menylbutyryl (methyl) carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, ethyl 4,6,9-triaza-4-benzyl-6,10-dimethyl-8-oxa -7-oxo-5,11-dithia-9-dodecenoate (OK 135), 1-methylthio (ethylideneamino) -N-methyl-N- (morpholinothio) carbamate (UC 51717); 3. from the group of carboxylic acid esters
• Bioallethrin ((S) -cyclopentyl isomer), bioresmethrin, biphenates, (RS) -1-cyano-1- (6-phenoxy-2-pyridyl) methyl- (1RS) -trans-3- (4-tert.butylphenyl) - 2,2-dimethylcyclopropane decarboxylate (NCI 85193), cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin, cyphenothrin, deltamethrin, empenthrin,
• Cyclopropanecarboxylic acid (2-naphthylmethyl) ester (Ro 12-0470), cyromazine, N- (3,5-dichloro-4- (1,1,2,3,3,3-hexafluoro-1-propyloxy) phenyl) carbomoyl ) -2-chlorobenzcarboximidic acid ethyl ester, DDT, diflubenzuron, N- (2,3-dihydro-3-methyl-1,3-thiazol-2-ylidenes) 2,4-xylidines, dinobutone, dinocap, endosulfan, ethofenprox, (4- Ethoxyphenyl) (dimethyl) (3- (3-phenoxyphenyl) propyl) silane, (4-ethoxyphenyl) (3- (4-fluoro-3-phenoxyphenyl) propyl) dimethylsilane,
• Fenoxycarb flubenzimine, flucycloxuron, flufenoxuron, gamma-HCH, hexythiazox, hydramethylnon (AC 217300), ivermectin, 2-nitromethyl-4,5-dihydro-6H-thiazine (SD 52618), 2-nitromethyl-3,4-dihydrothiazole ( SD 35651), 2-Nitromethylene-1,2-thiazinan-3-yIcarbamafdehyde (WL 108477), propargite, teflubenzuron, tetradifon, tetrasul, thiocyclam, triflumuron.
• Application forms can be from 0.00000001 up to 99% by weight of active ingredient
• the application takes place in a customary manner adapted to the application forms.
• the active compounds according to the invention are also suitable for controlling endoparasites and ectoparasites and nematodes in the veterinary field or in the field of animal husbandry.
• the active compounds according to the invention are used here in a known manner, such as by oral use in the form of, for example, tablets, capsules, drinkers, granules, by dermal use in the form of, for example, diving (dipping), spraying (spraying), pouring on (pour-on and spot) -on) and powdering and by parenteral use in the form of, for example, injection.
• novel compounds of the formula I according to the invention can accordingly also be particularly advantageous in animal husbandry (e.g. cattle, sheep, pigs and
• Poultry such as chickens, geese, etc.
• Poultry such as chickens, geese, etc.
• the animals are given the new compounds, if appropriate in suitable formulations (see above) and, if appropriate, orally with the drinking water or feed. Since excretion in the faeces is effective, the development of insects in the faeces of the animals can be prevented very easily in this way.
• the appropriate dosages and formulations depend in particular on the type and stage of development of the door and also on the infestation pressure and can be easily determined and determined using the usual methods.
• the new compounds can be used in cattle, for example, in doses of 0.01 to 1 mg / kg body weight. The following examples serve to explain the invention, without this being restricted thereto.
• Formulation examples a) A dusting agent is obtained by mixing 10 parts by weight of active compound and 90 parts by weight of talc as an inert substance and comminuting them in a hammer mill. b) A dispersion concentrate which is readily dispersible in water is prepared by adding 25 parts by weight of active compound, 65 parts by weight of kaolin-containing quartz as inert substance, 10 parts by weight of lignosulfonic acid potassium and 1 part by weight of oleoylmethyl tauric acid sodium as wetting and Mixes dispersant and grinds in a pin mill. c) A dispersion concentrate which is easily dispersible in water is prepared by mixing 40 parts by weight of active compound with 7 parts by weight of a
• An emulsifiable concentrate can be prepared from 15 parts by weight
• Granules can be produced from 2 to 15 parts by weight of active ingredient and
• an inert granule carrier material such as attapulgite, pumice granulate and / or quartz sand.
• a suspension of the wettable powder from example b) having a solids content of 30% is expediently used and sprayed onto the surface of an attapulgite granulate, dried and mixed intimately.
• the proportion by weight of the wettable powder is approximately 5% and that of the inert carrier material approximately 95% of the finished granulate.
• the ethanol is at room temperature in a vacuum. (12 Torr / 40 ° C), the
• Residue was taken up in water and extracted several times with ethyl acetate.

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