Classifications

• • 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
  • A01N43/88—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 six-membered rings with three ring hetero atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • 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
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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  • 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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  • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
  • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
  • A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
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  • 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
  • A01N43/12—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 condensed with a carbocyclic ring
• • A—HUMAN NECESSITIES
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  • 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
  • A01N43/24—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 two or more hetero atoms
  • A01N43/26—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 two or more hetero atoms five-membered rings
  • A01N43/28—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 two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
  • A01N43/30—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 two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
• • 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
  • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
  • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
• • 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
  • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero 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
  • 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
  • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
• • 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
  • A01N47/08—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 one or more single bonds to nitrogen atoms
  • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
  • A01N47/20—N-Aryl derivatives thereof
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P33/00—Antiparasitic agents
  • A61P33/14—Ectoparasiticides, e.g. scabicides
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • 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
  • C07C251/52—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
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • 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
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • 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
  • C07C251/58—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • 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
  • C07C251/60—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by carboxyl groups
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
  • C07C271/06—Esters of carbamic acids
  • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
  • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
  • C07C271/18—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by doubly-bound oxygen atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
  • C07C271/06—Esters of carbamic acids
  • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
  • C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
  • C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • 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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  • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
  • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
  • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
  • C07D241/12—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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  • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
  • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
  • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
  • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
  • C07D277/24—Radicals substituted by oxygen atoms
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  • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
  • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
  • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
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  • C07C2601/14—The ring being saturated

Definitions

• the present invention relates to novel substituted aryl oximes, processes for their preparation and their use as pesticides.
• Substituted aryloximes have already become known as pesticides (cf. WO2003 / 042147Al).
• a 2 -X is a bridging element. Between X and R 6 is optionally the bridging element,
• radicals R 21 and R 22 independently of one another represent hydrogen, nitro, hydroxyl, amino, cyano, cyanato, thiocyanato, formyl, halogen, in each case optionally cyano, halogen or C 1 -C 6 -alkoxy-substituted alkyl, alkoxy, alkylthio, Alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino or alkylcarbonylamino having in each case 1 to 4 carbon atoms in the alkyl groups, for C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxy carbonyl, CrQ-AJkoximinoformyl, Ci-C 4 alkoximino-acetyl, or C 2 -C 4 alkenyl or C 2 -C 4 alkynyl.
• a -X is either a direct bond or a straight-chain or branched or cyclic alkanediyl or an alkenediyl having in each case up to 8 carbon atoms and which in each case optionally in connection to the carbon chain is an oxygen atom,
• Sulfur atom or a moiety selected from SO, SO 2 , NH, N (C) -C 4 alkyl).
• a 2 -X also stands for
• R 9 is C r C 4 -alkyl or aryl
• a 2 -X furthermore represents a carbocyclic, optionally mono- or polyunsaturated, 5,6 or 7-membered ring system or an optionally mono- or polyunsaturated one
• Oxygen, sulfur, sulfonyl, sulfoxyl, carbonyl, NO, or optionally substituted by alkyl-substituted nitrogen may be interrupted and may optionally be mono- or polysubstituted.
• the attachment of these ring systems to the oxime oxygen always takes place via carbon.
• the attachment to the radical R 6 may be via carbon or a
• Heteroatom nitrogen or sulfur
• R 1 is hydrogen, nitro, hydroxy, amino, cyano, fluorine, chlorine, bromine, iodine, in each case optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy C r C 6 alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyloxy, C 3 -C 6 alkenyl, C 3 -C 6 alkenyl oxy, C 3 -C 6 alkynyl, C 3 -C 6 alkynyloxy, Ci-C 6 Alkylcarbonyloxy, C 1 -C 3 alkylsulfonyl,
• R 2 is hydrogen, nitro, hydroxyl, amino, cyano, cyanato, thiocyanato, formyl, halogen, in each case optionally cyano, halogen or by CpC 6 -alkoxy-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkyl amino or alkylcarbonylamino having in each case 1 to 6 carbon atoms in the alkyl groups, for CpC ⁇ -alkylcarbonyl, CpC 6 -alkoxycarbonyl, CpC 6 -alkoximinoformyl, Cp C ⁇ -alkoximino-acetyl, or for C 2 -C 6 -alkenyl or Ca-C ⁇ -alkynyl,
• R 3 is hydrogen, nitro, hydroxy, amino, cyano, halogen, in each case optionally substituted by cyano, halogen or Ci-Ce alkoxy-substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or alkylcarbonylamino each having 1 to 6 carbon atoms in the alkyl groups stands,
• R 4 is hydrogen, nitro, hydroxyl, amino, cyano, halogen, in each case optionally cyano, halogen or CpC 6 - alkoxy-substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or alkylcarbonylamino each having 1 to 6 carbon atoms in the alkyl groups,
• R 5 is hydrogen, straight-chain or branched or cyclic haloalkanyl or haloalkenyl having in each case up to 8 carbon atoms, aryl, substituted aryl,
• R 6 also represents a grouping -A 3 -Z, where A 3 represents a single bond or straight-chain or branched and optionally substituted by halogen or C 3 -C 6 -cycloalkyl-substituted alkanediyl having 1 to 6 carbon atoms and
• Z is optionally substituted by nitro, hydroxy, mercapto, amino, formyl, cyano, carboxy, carbamoyl, halogen, Ci-C 6 alkyl, C r C 6 hydroxyalkyl, CPQ-halo alkyl, CpC 6 alkyl-carbonyl, C -C 6 haloalkyl-carbonyl, C r C 6 alkoxy, CpC 6 - hydroxyalkoxy, CpC 6 haloalkoxy, CpC ⁇ -alkoxy-carbonyl, halo-CpC 6 alkoxy-carbonyl, Ci-C 6 -alkoxy-C 6 -alkyl, CpC 6 -haloalkoxy-CpC 6 -alkyl, Cp C 2 -alkylenedioxy, C 1 -C 2 -haloalkylenedioxy, C 1 -C 6 -alkoxyimino-C 1 -C 6 -alky
• N
• R> 6 also stands for one of the groupings:
• a 3 is a bond or an optionally single or multiple
• M is oxygen or NOR 7 .
• R 7 is alkyl 2 represents hydrogen, C, -C, C 3 -C 8 cycloalkyl, Q-CeAlkylcarbonyl, C 2 -C. 6
• C ⁇ -CöHaloalkenyloxy-C ⁇ alkyl C 3 -C 6 AUCyHyIoXy-Ci-C 6 AIlCyI, N (Cj-C 6 AIlCyI) 2 wherein the two alkyl groups are independently Ci-C 6 Al kylcarbonylamino, CpC ⁇ Haloalkylcarbonylamino, Ci-C ö Alkoxycarbonylamino and Ci-C ⁇ Alkylaminocarbonylamino can be.
• R 32 to R 35 are each independently halogen, Ci-C 4 alkyl, Ci-C 4 alkoxy (C r C 4 ) alkyl or halo (Ci-C 4 ) alkyl.
• n can take values from 0 to 3
• Each R 8 is independently hydrogen, halogen, halo (C 1 -C 4 ) alkyl, C 3 -
• R 10 and R 11 are each independently hydrogen, halogen, hydroxy, (Cr C4) alkyl, Haio (C 1 -C 4) alkyl or (C 1 -C 4) alkoxy or
• R 12 is (C r C 3 ) alkyl, (C 1 -C 3 ) alkoxy (C 1 -C 3 ) alkyl, aryl (C r C 3 ) alkyl, C 2 -C 4 alkenyl (C, -C 3 ) alkyl, halo (C 2 -C 4 ) alkenyl (C 1 -C 3 ) AlCl y, di (C r C 3 ) alkyl phosphonate, formyl, (C 1 -C 3 ) alkylcarbonyl, halo (C 1 -C 3 ) alkylcarbonyl, (Ci-C 3) alkoxy (C
• a 2 -X preferably represents a straight-chain or branched alkanediyl or alkenediyl having in each case up to 8 carbon atoms which optionally has, within the carbon chain, an oxygen atom, sulfur atom or a grouping selected from SO, SO 2 , NH, N (C 1 -C 4 ) Alkyl) and for
• R 9 is preferably methyl or aryl.
• a 2 -X particularly preferably represents a straight-chain or branched alkanediyl or alkenediyl having in each case up to 8 carbon atoms, which optionally contains an oxygen atom within the carbon chain and for
• R 9 particularly preferably represents methyl
• a 2 -X very particularly preferably represents a straight-chain or branched alkanediyl having up to 8 carbon atoms, optionally containing within the carbon chain an oxygen atom and is - (C r C 4 alkyl) - (CO) -O-, - (C C 1 -C 4 -alkyl) - (CO) - (NH) - or
• R 21 and R 22 independently of one another preferably represent hydrogen, nitro, hydroxyl, amino, cyano, cyanato, thiocyanato, formyl, halogen or methyl,
• R 21 and R 22 are particularly preferably hydrogen.
• R 1 preferably represents hydrogen, nitro, hydroxyl, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i- Propylthio, methylamino, ethylamino, n- or i-propylamino, dimethylamino or for the grouping -OA 1 , wherein A 1 has one of the meanings given above.
• R 1 particularly preferably represents hydrogen, nitro, hydroxyl, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i Propylthio, methylamino, ethylamino, n- or i-propylamino or dimethylamino.
• R 1 very particularly preferably represents hydrogen, methyl, ethyl, methoxy, ethoxy or fluorine, chlorine, bromine.
• R 2 is preferably hydrogen, nitro, cyano, cyanato, thiocyanato, formyl, halogen, in each case optionally substituted by cyano, halogen or Ci-C 5 alkoxy-substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or alkylcarbonylamino each having 1 to 5 Carbon atoms in the alkyl groups, for Ci-C 5 -alkyl-carbonyl, Ci-Cs-alkoxycarbonyl, Ci-C 5 -Alkoximinoformyl, Ci-Cs-alkoximino-acetyl, or for C 2 -C 5 alkenyl or
• R 2 particularly preferably represents hydrogen, nitro, cyano, cyanato, thiocyanato, formyl, fluorine, chlorine, bromine, iodine, in each case optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy methyl, ethyl , n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n - or i-Propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamin
• R 2 very particularly preferably represents hydrogen, cyano, fluorine, chlorine, bromine or iodine.
• R 2 most preferably represents hydrogen, fluorine, chlorine or bromine.
• R 3 preferably represents hydrogen, nitro, halogen, in each case optionally cyano, halogen or C] -C 5 -alkoxy-substituted alkyl, alkoxy, alkylthio or alkylamino having in each case 1 to 5 carbon atoms in the alkyl groups.
• R 3 particularly preferably represents hydrogen, nitro, fluorine, chlorine, bromine, iodine, in each case optionally cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n- , i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino.
• R 3 very particularly preferably represents hydrogen, cyano, fluorine, chlorine, bromine, methyl, ethyl, methoxy or ethoxy.
• R 4 preferably represents hydrogen, nitro, halogen, in each case optionally cyano, halogen or C 1 -C 5 -alkoxy-substituted alkyl, alkoxy, alkylthio or alkylamino having in each case 1 to 5 carbon atoms in the alkyl groups.
• R 4 particularly preferably represents hydrogen, nitro, fluorine, chlorine, bromine, iodine, in each case optionally cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n- , i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino.
• R 4 very particularly preferably represents hydrogen, cyano, fluorine, chlorine or bromine.
• R 5 preferably represents an alkanyl grouping or alkynyl grouping with 2 to
• R 5 particularly preferably represents hydrogen, methyl, isopropyl, cyclopropyl or cyclohexyl.
• R 5 is very particularly preferably methyl
• R 6 preferably represents an alkenyl grouping or alkynyl grouping with 2 to
• R 6 in which the radicals A 3 , Z, M, R 7 , W, n, R 8 , R 10 and R 11 have the following preferred or particularly preferred meanings are also preferred or particularly preferred to have.
• a 3 preferably represents a single bond or straight-chain or branched and optionally halogen or C 3 -C 6 -cycloalkyl-substituted alkanediyl having 1 to 6
• a 3 particularly preferably stands for a single bond or for each case optionally
• Methylene ethane-1, l-diyl (ethylidene), ethane-l, 2-diyl (dimethylene), propane-l, l-diyl (propylidene), propane-l, 2-diyl, propane-l, 3-diyl (Trimethylene), butane-1,1-diyl (butylidene) or butane-1,4-diyl (tetramethylene),
• a 3 very particularly preferably represents a single bond or methylene
• Z is preferably in each case optionally nitro, hydroxy, amino, formyl, cyano, carboxy, carbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, Fluoromethyl, chloromethyl, difluoromethyl, dichloromethyl, trifluoromethyl,
• M is preferably oxygen
• R 7 is preferably hydrogen; C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 alkylcarbonyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, aryl, heterocyclyl or benzyl, where alkyl, cycloalkyl, alkenyl and alkynyl radicals are unsubstituted or optionally substituted one to five times with a radical from the following group: halogen, -N 3 , CN, NO 2 , OH, SH, C r C 4 alkoxy, CpC 4 haloalkoxy, C 2 -C 4 alkenyloxy, C 2 -C 4 haloalkenyloxy, C 3 -
• W preferably stands for "C (R 32 R 33 ) and * C (R 32 R 33 ) C (R 34 R 35 ), where the star” * "
• R 32 to R 35 are each independently and in each case halogen, C 1 -C 3 -alkyl, C 1 -C 3 -alkoxy (C 1 -C 3) -alkyl or halo (C 1 -C 3 ) -alkyl,
• W is particularly preferably C (R 32 R 33 ), where R 32 R 33 is halogen or Ci-C ⁇ Alkyl.
• W is very particularly preferably C (R 32 R 33 ), where R 32 R 33 is halogen or methyl.
• n preferably takes on values of 0 to 2.
• n is particularly preferably 0.
• R 8 is preferably in each case independently of one another hydrogen, halogen, Halo (Q -C 4 ) alkyl or nitro.
• R 8 particularly preferably represents hydrogen.
• the compounds of formula (I) may also be optionally substituted as stereoisomers, i.e., depending on the nature of the substituents. are present as geometric and / or optical isomers or isomer mixtures in different compositions. Both the pure stereoisomers and any mixtures of these isomers are the subject of this invention, even though in general only the compounds of the formula (I) are mentioned here.
• the invention also provides the salt-like derivatives formed from compounds of the formula (I) by reaction with basic or acidic compounds.
• hydrocarbon radicals such as alkyl - also in combination with heteroatoms, such as in alkoxy - as far as possible in each case straight-chain or branched.
• the new substituted aryloximes of the general formula (I) have interesting biological properties. They are characterized in particular by strong arthropodizide (insecticidal and acaricidal) and nematicidal activity and can be used in agriculture, in forests, in the protection of stored products and in the hygiene sector.
• novel substituted aryloximes of the general formula (I) can be prepared according to the general reaction scheme below.
• the synthesis of the starting compounds of the formula (II) is described in DE 103 20 782 A1.
• LG leaving group such. Cl or methanesulfonyloxy (MeS ⁇ 2 ⁇ -)
• the precursors of the general formula H 2 NOA 2 -XR 6 are accessible via the following reaction route.
• substituents of the compounds of formula such as substituent R 1 may also be modified in further reaction steps.
• R 1 is halogen, in particular fluorine
• nucleophilic exchange with suitable nucleophiles can be carried out in the presence of the basic reaction auxiliaries mentioned below in the context of the substituent definition of R 1
• the starting materials of the general formula (D) are known and / or can be prepared by processes known per se (see Preparation Examples).
• reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, preferably at temperatures between 0 0 C and 150 0 C, between 1O 0 C and 120 0 C.
• the process according to the invention is generally carried out under normal pressure. However, it is also possible to carry out the process according to the invention under elevated or reduced pressure-generally between 0.1 bar and 10 bar.
• the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess.
• the reaction is generally carried out in a suitable diluent in the presence of a reaction aid and the reaction mixture is generally stirred for several hours at the required temperature.
• the workup is carried out by customary methods (see the preparation examples).
• the compounds of the general formula (I) according to the invention can be converted into other compounds of the general formula (I) by methods known in principle. Some of these possible conversion reactions are outlined below by way of example:
• salts with bases and salts ("adducts") with acids preferably salts with inorganic bases, such as alkali metal salts, for example sodium, potassium or cesium salts, alkaline earth metal salts, for example calcium or magnesium salts, ammonium salts, salts with organic bases, in particular with organic amines, for example triethylammonium, dicyclohexylammonium, N, N'-dibenzylethylenediammonium, pyridinium, picolinium or ethanolammonium salts, salts with inorganic acids, for example hydrochlorides, hydrobromides, dihydrosulfates, trihydrosulfates or phosphates, salts with organic carboxylic acids or organic sulfonic acids, for example formates, acetates, trifluoroacetates
• Salts are formed according to standard salt preparation procedures.
• the compounds of this invention are reacted with appropriate acids to form acid addition salts.
• Representative acid addition salts are salts which are exemplified by the Reaction with inorganic acids, such as, for example, sulfuric acid, hydrochloric acid, hydrobromic acid, phosphoric acid or organic carboxylic acids such as acetic acid, trifluoroacetic acid, citric acid, succinic acid, lactic acid, formic acid, maleic acid, camphoric acid, phthalic acid, glycolic acid, glutaric acid, stearic acid, salicylic acid, sorbic acid, cinnamic acid, picric acid, Benzoic acid or organic sulfonic acids such as methanesulfonic acid and para-toluenesulfonic acid form.
• inorganic acids such as, for example, sulfuric acid, hydrochloric acid, hydrobromic acid, phosphoric acid or organic carboxylic acids such as acetic acid
• the compounds of formula (I) may optionally be present in different polymorphic forms or as a mixture of different polymorphic forms. Both the pure polymorphs and the polymorph mixtures are the subject of the invention and can be used according to the invention.
• the active compounds according to the invention are suitable for plant tolerance, favorable warm-blood toxicity and good environmental compatibility for the protection of plants and plant organs, for increasing crop yields, improving the quality of the crop and for controlling animal pests, in particular insects, arachnids, helminths, nematodes and molluscs which are found in agriculture, horticulture, livestock, forests, gardens and recreational facilities, in the protection of materials and materials and in the hygiene sector. They can preferably be used as crop protection agents. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
• the above mentioned pests include:
• Anoplura e.g. Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Trichodectes spp.
• arachnids e.g. Acarus siro, Aceria sheldoni, Aculops spp., Aculus spp., Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Chorioptes spp., Dermanyssus gallinae, Eotetranychus spp., Epitrimerus pyri, Eutetranychus spp.
• Eriophyes spp. Hemitarsonemus spp., Hyalomma spp., Ixodes spp., Latrodectus mactans, Metatetranychus spp., Oligonychus spp., Ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp. Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Stenotarsonemus spp., Tarsonemus spp., Tetranychus spp., Vasates lycopersici.
• Gastropoda e.g. Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Succinea spp.
• helminths from the class of helminths, for example, Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp., Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia timori, Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp., Dicrocoelium spp , Dictyocaulus filaria, Diphyllobothrium latum, Dracunculus medinensis, Echinococcus granulosus, Echinococcus multilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp., Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Lo
• protozoa such as Eimeria
• Eimeria protozoa
• Heliopeltis spp. Horcias nobilellus, Leptocorisa spp., Leptoglossus phyllopus, Lygus spp., Macropes excavatus, Miridae, Nezara spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., Psallus seriatus, Pseudacysta persea, Rhodnius spp. Sahlbergella singularis, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp.
• Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
• Pseudoplusia includens, Pyrausta nubilalis, Spodoptera spp., Thermesia gemmatalis, Tinea pellionella, Tineola bisselliella, Tortrix viridana, Trichoplusia spp.
• Orthoptera e.g. Acheta domesticus, Blatta orientalis, Blattella germanica, Gryllotalpa spp., Leucophaea maderae, Locusta spp., Melanoplus spp., Periplaneta americana, Schistocerca gregaria.
• siphonaptera e.g. Ceratophyllus spp., Xenopsylla cheopis.
• Symphyla e.g. Scutigerella immaculata.
• Thysanoptera e.g. Basothrips biformis, Enneothrips flavens, Frankliniella spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamoni, Thrips spp.
• Thysanura e.g. Lepisma saccharina.
• the plant parasitic nematodes include, for example, Anguina spp., Aphelenchoides spp., Belonoaimus spp., Bursaphelenchus spp., Ditylenchus dipsaci, Globodera spp., Heliocotylenchus spp., Heterodera spp., Longidorus spp., Meloidogyne spp., Pratylenchus spp., Radopholus similis, Rotylenchus spp., Trichodorus spp., Tylenchorhynchus spp., Tylenchulus spp., Tylenchulus semipenetrans, Xiphinema spp.
• the compounds of the formula (I) according to the invention are notable in particular for their strong action against ...
• the compounds according to the invention may also be used in certain concentrations or application rates as herbicides, safeners, growth regulators or agents for improving plant properties, or as microbicides, for example as fungicides, antimycotics, bactericides, viricides (including anti-viral agents) or as anti-MLO agents ( Mycoplasma-like-organism) and RLO (Rickettsia-like-organism). If appropriate, they can also be used as intermediates or precursors for the synthesis of further active ingredients.
• plants and parts of plants can be treated.
• plants are understood as meaning all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
• Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or can not be protected by plant breeders' rights.
• Plant parts are to be understood as meaning all aboveground and underground parts and organs of the plants, such as shoot, leaf, flower and root, by way of example leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds and roots, tubers and rhizomes.
• the plant parts also include crops and vegetative and generative propagation material, such as cuttings, tubers, rhizomes, offshoots and seeds.
• the treatment according to the invention of the plants and plant parts with the active ingredients is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment methods, e.g. by dipping, spraying, evaporating, atomizing, spreading, brushing, injecting and in propagating material, in particular in seeds, further by single or multilayer coating.
• the active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, scattering granules, suspension-emulsion concentrates, active substance-impregnated natural products, Active substance-impregnated synthetic substances, fertilizers and ultrafine encapsulations in polymeric substances.
• customary formulations such as solutions, emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, scattering granules, suspension-emulsion concentrates, active substance-impregnated natural products, Active substance-impregnated synthetic substances, fertilizers and ultrafine encapsulations in polymeric substances.
• formulations are prepared in a known manner, e.g. by mixing the active compounds with extenders, ie liquid solvents and / or solid carriers, if appropriate using surface-active agents, ie emulsifiers and / or dispersants and / or foam-forming agents.
• extenders ie liquid solvents and / or solid carriers
• surface-active agents ie emulsifiers and / or dispersants and / or foam-forming agents.
• Excipients which can be used are those which are suitable for imparting special properties to the composition itself and / or preparations derived therefrom (for example spray liquor, seed dressing), such as certain technical properties and / or specific biological properties.
• Typical auxiliaries are: extenders, solvents and carriers.
• polar and non-polar organic chemical liquids e.g. from the classes of aromatic and non-aromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which may also be substituted, etherified and / or esterified), ketones (such as acetone, cyclohexanone), Esters (including fats and oils) and (poly) ethers, simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as dimethyl sulfoxide).
• aromatic and non-aromatic hydrocarbons such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes
• alcohols and polyols which may also be substituted, etherified and / or esterified
• ketones such
• Suitable liquid solvents are essentially: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g.
• Petroleum fractions mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethyl sulfoxide, and water.
• Suitable solid carriers are:
• ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic minerals, such as finely divided silica, alumina and silicates, as solid carriers for granules in question: eg broken and fractionated natural rocks such Calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as paper, sawdust, coconut shells, corn cobs and tobacco stalks; suitable emulsifiers and / or foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene , _
• Fatty alcohol ethers e.g. Alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and protein hydrolysates;
• suitable dispersants are non-ionic and / or ionic substances, e.g.
• Adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-type polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids may be used in the formulations.
• Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
• inorganic pigments e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
• additives may be fragrances, mineral or vegetable optionally modified oils, waxes and nutrients (also trace nutrients), such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
• Stabilizers such as cold stabilizers, preservatives, antioxidants, light stabilizers or other chemical and / or physical stability-improving agents may also be present.
• the formulations generally contain between 0.01 and 98% by weight of active ingredient, preferably between 0.5 and 90%.
• the active ingredient according to the invention may be present in its commercial formulations as well as in the formulations prepared from these formulations in admixture with other active ingredients such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, safeners, fertilizers or semiochemicals.
• active ingredients such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, safeners, fertilizers or semiochemicals.
• Particularly favorable mixing partners are, for example, the following:
• bilanafos binapacryl; biphenyl; bitertanol; Blasticidin-S; bromuconazole; Bupirimate;
• Buthiobate butylamine; Calcium polysulfides; capsimycin; captafol; captan; carbendazim;
• carboxin Ca ⁇ ropamid; carvones; chinomethionat; Chlobenthiazone; Chlorfenazole; chloroneb;
• chlorothalonil chlozolinate; Clozylacon; cyazofamid; cyflufenamid; cymoxanil; Cyproconazoles; cyprodinil; cyprofuram; Dagger G; debacarb; dichlofluanid; dichlone; dichlorophen;
• fluoromides fluoxastrobin; fluquinconazole; flurprimidol; flusilazole; flusulfamide; flutolanil;
• flutriafol flutriafol; folpet; Fosetyl-Al; Fosetyl-sodium; fuberidazole; furalaxyl; furametpyr; Furcarbanil;
• iprobenfos iprodione; iprovalicarb; Irumamycin; isoprothiolane; Isovaledione; kasugamycin;
• Metalaxyl-M metconazole; methasulfocarb; Methfuroxam; metiram; metominostrobin;
• phosdiphen phthalides; picoxystrobin; piperalin; Polyoxins; Polyoxorim; Probenazole; prochloraz;
• procymidone propamocarb; Propanosine-sodium; propiconazole; propineb; proquinazid;
• prothioconazole pyraclostrobin; Pyrazohos; pyrifenox; pyrimethanil; pyroquilon; Pyroxyfur; Pyrrolnitrine; Quinconazole; quinoxyfen; quintozene; Simeconazole; spiroxamine; Sulfur;
• tebuconazole tecloftalam; Tecnazene; Tetcyclacis; tetraconazole; thiabendazole; Thicyofen;
• Thifluzamide Thiophanate-methyl; thiram; Tioxymid; Tolclofos-methyl; tolylfluanid; Triadimefon; triadimenol; Triazbutil; triazoxide; Tricyclamide; Tricyclazole; Tridemo ⁇ h;
• trifloxystrobin triflumizole; triforine; triticonazole; Uniconazole; Validamycin A; vinclozolin; Zineb; ziram; zoxamide; (2S) -N- [2- [4 - [[3- (4-chlo ⁇ henyl) -2-propynyl] oxy] -3-methoxyphenyl] - ethyl] -3-methyl-2 - [(methylsulfonyl) amino] -butanamide; l- (l-naphthalenyl) -lH-pyrrole-2,5-dione; 2,3,5,6-tetrachloro-4- (methylsulfonyl) -pyridine; 2-amino-4-methyl-N-phenyl-5-thiazolecarboxamide; 2-chloro-N- (2,3-dihydro-l, l, 3-trimethyl-lH-inden-4-yl) -3-pyridinecarboxamides
• Carbamates for example alanycarb, aldicarb, aldoxycarb, allyxycarb, aminocarb, bendiocarb, benzuracarb, bufencarb, butacarb, butocarboxime, butoxycarboxim, carbaryl, carbofuran, carbosulfan, cloethocarb, dimetilane, ethiofencarb, fenobucarb, fenothiocarb, formetanate, furathiocarb, isoprocarb , Metam-sodium, Methiocarb, Methomyl,
• Organophosphates for example acephates, azamethiphos, azinphos (-methyl, -ethyl), bromophos-ethyl, bromfenvinfos (-methyl), butathiofos, cadusafos, carbophenothione, chloroethoxyfos,
• Chlorfenvinphos Chlormephos, chlo ⁇ yrifos (-methyl / -ethyl), coumaphos, cyanofephos, cyanophos, chlorfenvinphos, demeton-S-methyl, demeton-S-methylsulphone,
• Isofenphos Isopropyl O-Salicylate, Isoxathione, Malathion, Mecarbam, Methacrifos, Methamidophos, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion (-methyl / -ethyl), Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidon, Phosphocarb, Phoxim, Pirimiphos (-methyl / -ethyl), Profenofos, Propaphos, Propetamphos, Prothiofos, Prothoate, Pyraclofos, Pyridaphenthion, Pyridathion, Quinalphos, Sebufos, Sulfotep, Sulprofos, Tebupirimfos, Temephos, Terbufos,
• pyrethroids for example acrinathrin, allethrin (d-cis-trans, d-trans), beta-cyfluthrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentyl isomer, bioethanomethrin, biopermethrin, bioresmethrin, chlovaporthrin, cis-cypermetbxin, Cis-resmethrin, cis-permethrin, clocthrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin (alpha, beta, theta, zeta), cyphenothrin, deltamethrin, empenthrin (IR isomer), esfenvalerate, etofenprox, fenfluthrin, Fenpropathrin, f
• Chlomicotinyls for example acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazines, thiacloprid, thiamethoxam
• Acetylcholine receptor modulators are Acetylcholine receptor modulators
• Organochlorines for example, camphechlor, chlordane, endosulfan, gamma-HCH, HCH, heptachlor, lindane, methoxychlor
• Fiproles for example acetoprole, ethiprole, fipronil, pyrafluprole, pyriprole, vaniliprole
• Mectins for example avermectin, emamectin, emamectin benzoate, ivermectin, milbemycin
• Juvenile hormone mimetics for example, diofenolan, epofenonans, fenoxycarb, hydroprene, kinoprenes, methoprenes, pyriproxifen, triprene
• Diacylhydrazines for example chromafenozides, halofenozides, methoxyfenozides, tebufenozides
• Benzoylureas for example bistrifluron, chlorofluazuron, diflubenzuron, fluazuron, flucycloxuron, fenphenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron, triflumuron
• Organotin compounds for example azocyclotin, cyhexatin, fenbutatin oxides Decoupling of oxidative phosphorylation by interruption of the H proton gradient
• METI's for example Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad
• Tetronic acids for example spirodiclofen, spiromesifen
• Tetramic acids for example spirotetramat (CAS Reg. No .: 203313-25-1) and 3- (2,5-dimethylphenyl) -8-methoxy-2-oxo-1-azaspiro [4.5] dec-3-ene 4-yl ethyl carbonate (also known as: Carbonic acid, 3- (2,5-dimethylphenyl) -8-methoxy-2-oxo-1-azaspiro [4.5] dec-3-en-4-yl ethyl ester, CAS Reg. No .: 382608-10-8) Carboxamides, for example flonicamide
• Octopaminergic agonists for example, amitraz
• Activators of the Ryanodine sensitive Caclcium channel e.g.
• Benzoic acid dicarboxamides for example flubendiamides
• Nereistoxin analogs for example thiocyclam hydrogen oxalate, thiosultap-sodium
• fumigants for example aluminum phosphides, methyl bromides, sulfuryl fluorides
• feed inhibitors for example cryolites, flonicamide, pymetrozines
• the active compounds according to the invention can furthermore be present when used as insecticides in their commercial formulations as well as in the formulations prepared from these formulations in admixture with synergists.
• Synergists are compounds which increase the effect of the active ingredients without the added synergist itself having to be active.
• the active compounds according to the invention may furthermore, when used as insecticides in their commercial formulations and in the forms of use prepared from these formulations, be present in mixtures with inhibitors which reduce degradation of the active ingredient after application in the environment of the plant, on the surface of plant parts or in plant tissues ,
• the active substance content of the application forms prepared from the commercial formulations can vary within wide ranges.
• the active ingredient concentration of the use forms may be from 0.00000001 up to 95% by weight of active compound, preferably between 0.00001 and 1% by weight.
• the application is done in a custom forms adapted to the application.
• plants and their parts can be treated.
• wild-type or plant species obtained by conventional biological breeding methods, such as crossing or protoplast fusion, and plant cultivars and their parts are treated.
• transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated.
• the terms "parts” or “parts of plants” or “plant parts” have been explained above.
• Plant varieties are understood as meaning plants having new traits which have been bred by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be varieties, biotypes and genotypes.
• the treatment according to the invention may also give rise to superadditive ("synergistic") effects.
• superadditive are degraded Application rates and / or enhancements of the spectrum of action and / or enhancement of the effect of the substances and agents usable according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering efficiency, easier harvest, Acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products possible, which go beyond the expected effects actually.
• the preferred plants or plant cultivars to be treated according to the invention include all plants which, as a result of the genetic engineering modification, obtained genetic material which gives these plants particularly advantageous valuable properties ("traits").
• traits are better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to bottoms salt, increased flowering, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products , higher shelf life and / or workability of the harvested products.
• Further and particularly emphasized examples of such properties are an increased defense of the plants against animal and microbial pests, as against insects, mites, phytopathogenic fungi, bacteria and / or viruses as well as an increased tolerance of the plants against certain herbicidal active substances.
• transgenic plants are the important crops such as cereals (wheat, rice), corn, soybeans, potatoes, sugar beets, tomatoes, peas and other vegetables, cotton, tobacco, oilseed rape and fruit plants (with the fruits apples, pears, citrus fruits and Grapes), with special emphasis on maize, soya, potato, cotton, tobacco and oilseed rape.
• Bt plants are the increased defense of the plants against insects, arachnids, nematodes and snails by toxins produced in the plants, in particular those which are produced by the genetic material from Bacillus thuringiensis (eg by the genes Cry ⁇ A (a) , CryIA (b), Cry ⁇ A (c), CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF, and combinations thereof) in the plants (hereinafter "Bt plants”).
• Bacillus thuringiensis eg by the genes Cry ⁇ A (a) , CryIA (b), Cry ⁇ A (c), CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF, and combinations thereof
• Traits also highlight the increased resistance of plants to fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins. Traits which are furthermore particularly emphasized are the increased tolerance of the plants to certain herbicidally active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg "PAT" gene).
• the genes which confer the desired properties can also be combined with one another in combinations with one another transgenic plants occur.
• Bt plants are maize varieties, cotton varieties, soybean varieties and potato varieties, which are sold under the trade names YBELD GARD® (eg corn, cotton, soya), KnockOut® (eg corn), StarLink® (eg corn), Bollgard® ( Cotton), Nucotn® (cotton) and NewLeaf® (potato).
• YBELD GARD® eg corn, cotton, soya
• KnockOut® eg corn
• StarLink® eg corn
• Bollgard® Cotton
• Nucotn® cotton
• NewLeaf® potato
• herbicide-tolerant plants are maize varieties, cotton varieties and soybean varieties, which are sold under the trade names Roundup Ready® (tolerance to glyphosate eg corn, cotton, soy), Liberty Link® (tolerance to phosphinotricin, eg rapeseed), IMI® (tolerance against imidazolinone) and STS® (tolerance to sulfonylureas eg corn).
• Roundup Ready® tolerance to glyphosate eg corn, cotton, soy
• Liberty Link® tolerance to phosphinotricin, eg rapeseed
• IMI® tolerance against imidazolinone
• STS® tolerance to sulfonylureas eg corn
• Clearfield® varieties eg corn
• the listed plants can be treated particularly advantageously according to the invention with the compounds of the general formula I or the active substance mixtures according to the invention.
• the preferred ranges given above for the active compounds or mixtures also apply to the treatment of these plants.
• Particularly emphasized is the plant treatment with the compounds or mixtures specifically mentioned in the present text.
• the active compounds of the invention not only against plant, hygiene and storage pests, but also in the veterinary sector against animal parasites (ecto- and endoparasites) such as ticks, leather ticks, mange mites, running mites, flies (stinging and licking), parasitic fly larvae, lice , Hair pieces, featherlings and fleas.
• animal parasites ecto- and endoparasites
• ticks ecto- and endoparasites
• leather ticks such as ticks, leather ticks, mange mites, running mites, flies (stinging and licking), parasitic fly larvae, lice , Hair pieces, featherlings and fleas.
• flies stinging and licking
• parasitic fly larvae such as ticks, leather ticks, mange mites, running mites, flies (stinging and licking), parasitic fly larvae, lice , Hair pieces, featherlings and fleas.
• Anoplurida e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.
• Trimenopon spp. Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp.
• siphonaptrida e.g. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.
• heteropterid e.g. Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.
• Actinedida Prostigmata
• Acaridida e.g. Acarapis spp., Cheyletiella spp., Ornitrocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp , Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.
• the active compounds of the formula (I) according to the invention are also suitable for controlling arthropods which are farm animals, such as e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as e.g. Dogs, cats, caged birds, aquarium fish and so-called experimental animals, such. Hamsters, guinea pigs, rats and mice.
• arthropods are farm animals, such as e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as e.g. Dogs, cats, caged birds, aquarium fish and so-called experimental animals, such. Hamsters, guinea pigs, rats and mice.
• the application of the active compounds according to the invention takes place in the veterinary sector and in animal husbandry in a known manner by enteral administration in the form of, for example, tablets, capsules, infusions, drenches, granules, pastes, boilies, the feed-through process, suppositories, by parenteral administration, as by injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, by nasal application, by dermal application in the form of, for example, diving or bathing (dipping), spraying, pouring (pour-on and spot-on ), the washing, the Einpudems and with the help of active substance-containing moldings, such as collars, ear tags, tail marks, limb bands, holsters, marking devices, etc.
• enteral administration in the form of, for example, tablets, capsules, infusions, drenches, granules, pastes, boilies, the feed-through process, suppositories
• parenteral administration as by
• the active compounds of the formula (I) can be used as formulations (for example powders, emulsions, flowable agents) which contain the active ingredients in an amount of from 1 to 80% by weight, directly or apply after 100 to 10,000 times dilution or use as a chemical bath.
• formulations for example powders, emulsions, flowable agents
• the compounds according to the invention show a high insecticidal activity against insects which destroy industrial materials.
• insects By way of example and preferably without limiting however, the following insects are mentioned:
• Hymenoptera such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur;
• Termites such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus;
• Non-living materials such as preferably plastics, adhesives, glues, papers and cardboard, leather, wood, wood processing products and paints.
• the ready-to-use agents may optionally contain further insecticides and optionally one or more fungicides.
• the compounds according to the invention can be used to protect against fouling of objects, in particular hulls, sieves, nets, structures, quay systems and signal systems, which come into contact with seawater or brackish water. Furthermore, the compounds according to the invention can be used alone or in combinations with other active substances as antifouling agents.
• the active compounds are also suitable for controlling animal pests in household, hygiene and storage protection, in particular of insects, arachnids and mites, which are used in closed rooms, such as apartments, factory buildings, offices, vehicle cabins u.a. occurrence. They can be used to control these pests, alone or in combination with other active ingredients and adjuvants in household insecticide products. They are effective against sensitive and resistant species and against all stages of development. These pests include:
• Acarina e.g. Argas persicus, Argas reflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus, Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae.
• Opiliones e.g. Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, Opiliones phalangium.
• Zygentoma e.g. Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus.
• Diptera e.g. Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles spp., Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Musca domestica, Phlebotomus spp., Sarcophaga carnaria, Simulium spp., Stomoxys Calcitrans, Tipula paludosa.
• Lepidoptera e.g. Achroia grisella, Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.
• Ctenocephalides canis Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.
• Hymenoptera e.g. Camponotus herculeanus, Lasius f ⁇ iliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.
• Heteroptera e.g. Cimex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans.
• the application is carried out in aerosols, non-pressurized sprays, eg pump and atomizer sprays, smoke machines, Foggem, foams, gels, evaporator products with evaporator plates of cellulose or plastic, liquid evaporators, gel and membrane evaporators, propeller driven evaporators, energy-less or passive evaporation systems, moth papers, moth cakes and moth gels, as granules or dusts, in straw baits or bait stations.
• reaction solution turned brown and is stirred at RT overnight.
• the reaction mixture is poured into 1.5 1 of water and extracted several times with a hexane / ethyl acetate mixture (1: 1).
• the combined organic phases are washed twice with water, dried over Na 2 SO 4 , filtered and concentrated to dryness.
• the crude product is recrystallized from hexane / ethyl acetate. There were obtained 20.5 g of clean 1- (3-chloro-2,5-dihydroxyphenyl) -ethanone and 28.5 g of slightly contaminated product.
• the crude product is taken up in 250 ml of ethanol, admixed with IN-NaOH and stirred under reflux for several hours until the conversion is complete after TLC monitoring.
• the batch is concentrated by dryness to enable the residue with water, brought with HCl to pH ⁇ 7 and extracted several times with EA, dried over Na 2 SO4, filtered 'and evaporated to dryness.
• the crude product is purified by flash chromatography on silica gel (gradient: hexane / ethyl acetate 4: 1 to ethyl acetate 100%). Two fractions of the product are obtained, 4.6 g (100% purity by LC-MS) and 1.3 g (95% purity by LC-MS).
• a solution of 68 g of an approximately 2: 1 mixture of 1- (2-hydroxy-5-methoxyphenyl) cyclopropyl ketone and (2,5-dimethoxyphenyl) cyclopropyl ketone in DMF is added under protective gas within 1 h in portions with 57.2 g N-chlorosuccinimide added.
• the reaction solution turned brown and is stirred at RT overnight.
• the reaction mixture is poured onto 600 ml of water; 53 g of (3-chloro-2-hydroxy-5-methoxyphenyl) cyclopropyl ketone are obtained as a beige solid.
• Emulsifier 0.5 part by weight of alkylaryl polyglycol ether
• active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
• Maize leaf discs (Zea mays) are sprayed with an active compound preparation of the desired concentration and, after drying, are infested with caterpillars of the armyworm (Spodoptera frugiperdä).
• the effect is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillar has been killed.
• Emulsifier 0.5 part by weight of alkylaryl polyglycol ether
• active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
• Chinese cabbage leaf discs (Brassica pekinensis) are sprayed with an active compound preparation of the desired concentration and, after drying, are populated with larvae of the horseradish leaf beetle (Phaedon cochleariae).
• the effect is determined in%. 100% means that all beetle larvae have been killed; 0% means that no beetle larvae have been killed.
• the active compound is mixed with the stated amounts of solvent and the concentrate is diluted with water to the desired concentration.
• the Aedsae aegypti larvae (third Laevstadium L3) are treated with an active compound preparation of the desired concentration.
• the effect is determined in%. 100% means that all Aedsae aegypti have been killed; 0% means that no Aedsae aegypti have been killed and -1 means unreadable.

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• 2005
  • 2005-05-14 DE DE102005022384A patent/DE102005022384A1/de not_active Withdrawn
• 2006
  • 2006-05-06 US US11/920,266 patent/US20090221596A1/en not_active Abandoned
  • 2006-05-06 EP EP06849372A patent/EP1883622A1/de not_active Withdrawn
  • 2006-05-06 KR KR1020077029002A patent/KR20080015443A/ko not_active Application Discontinuation
  • 2006-05-06 CN CNA2006800207833A patent/CN101193855A/zh active Pending
  • 2006-05-06 JP JP2008510470A patent/JP2008540474A/ja active Pending
  • 2006-05-06 WO PCT/EP2006/004256 patent/WO2007090434A1/de active Application Filing
  • 2006-05-06 BR BRPI0611271-4A patent/BRPI0611271A2/pt not_active IP Right Cessation
  • 2006-05-11 AR ARP060101905A patent/AR054190A1/es unknown
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