EP1883622A1 - Substituted aryl oximes - Google Patents

Substituted aryl oximes

Info

Publication number
EP1883622A1
EP1883622A1 EP06849372A EP06849372A EP1883622A1 EP 1883622 A1 EP1883622 A1 EP 1883622A1 EP 06849372 A EP06849372 A EP 06849372A EP 06849372 A EP06849372 A EP 06849372A EP 1883622 A1 EP1883622 A1 EP 1883622A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
alkoxy
spp
alkenyl
cyano
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP06849372A
Other languages
German (de)
French (fr)
Inventor
Iris Escher
Michael Müller
Peter Jeschke
Michael Beck
Oliver Gaertzen
Olga Malsam
Peter Lösel
Ulrich Ebbinghaus-Kintscher
Christian Arnold
Karl-Josef Haack
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Bayer CropScience AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of EP1883622A1 publication Critical patent/EP1883622A1/en
Withdrawn legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—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
    • 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
    • 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
    • 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
    • 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
    • A01N43/02—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
    • 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • 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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    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • 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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    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
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    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • 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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Abstract

The invention relates to compounds of the formula (I) in which A<SUP>1</SUP>, A<SUP>2</SUP>, R<SUP>1</SUP>, R<SUP>2</SUP>, R<SUP>3</SUP>, R<SUP>4</SUP>, R<SUP>5</SUP> and X have the definition specified in the description, to processes and intermediates for preparing them and to their use for controlling pests.

Description

Substituierte AryloximeSubstituted aryloximes
Gegenstand der vorliegenden Erfindung sind neue substituierte Aryloxime, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel.The present invention relates to novel substituted aryl oximes, processes for their preparation and their use as pesticides.
Substituierte Aryloxime sind bereits als Schädlingsbekämpfungsmittel bekannt geworden (vgl.WO2003/042147Al).Substituted aryloximes have already become known as pesticides (cf. WO2003 / 042147Al).
Es wurden nun neue substituierte Aryloxime der allgemeinen Formel (I) gefunden,New substituted aryloximes of the general formula (I) have now been found,
in welcherin which
A1 für eine der Gruppierungen -CH2-CH=CCl2, -CH2-CH=CBr2, -CH2-CH=CClF, -CH2- CF=CCl2, -(CHz)2-CH=CF2, -CH2-CH=CBrCl, -CH2-CH=CBrF, -CF=CH-CH=CH2, -CH2- CF=CF-CH=CH2, -CH2-CH=CClCF3, -(CH2)2-C(Halogen)3, -(CH2)2-CH(Halogen)2) -CH2- CH(Halogen)-CH(Halogen)2, -CH2-CH=CClCH3 steht und in welcherA 1 represents one of the groupings -CH 2 -CH = CCl 2 , -CH 2 -CH = CBr 2 , -CH 2 -CH = CClF, -CH 2 - CF = CCl 2 , - (CHz) 2 -CH = CF 2 , -CH 2 -CH = CBrCl, -CH 2 -CH = CBrF, -CF = CH-CH = CH 2 , -CH 2 - CF = CF-CH = CH 2 , -CH 2 -CH = CClCF 3 , - (CH 2 ) 2 -C (halogen) 3 , - (CH 2 ) 2 -CH (halo) 2) -CH 2 -CH (halo) -CH (halo) 2 , -CH 2 -CH = CClCH 3 and in which
A2-X ein verbrückendes Element ist. Zwischen X und R6 befindet sich gegebenenfalls das verbrückende Element,A 2 -X is a bridging element. Between X and R 6 is optionally the bridging element,
in dem die Reste R21 und R22 unabhängig voneinander für Wasserstoff, Nitro, Hydroxy, Amino, Cyano, Cyanato, Thiocyanato, Formyl, Halogen, für jeweils gegebenenfalls durch Cyano, Halogen oder Ci-Cβ-Alkoxy substituiertes Alkyl, Alkoxy, Alkylthio, Alkylsulfinyl, Alkylsulfonyl, Alkylamino, Dialkylamino oder Alkylcarbonylamino mit jeweils 1 bis 4 Kohlenstoffatomen in den Alkylgruppen, für Ci-C4-Alkyl-carbonyl, Ci-C4-Alkoxy- carbonyl, CrQ-AJkoximinoformyl, Ci-C4-Alkoximino-acetyl, oder für C2-C4-Alkenyl oder C2-C4-Alkinyl stehen.in which the 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 steht entweder für eine direkte Bindung oder für ein geradkettiges oder verzweigtes oder cyclisches Alkandiyl oder ein Alkendiyl mit jeweils bis zu 8 Kohlenstoffatomen und welche jeweils gegebenenfalls in Anknüpfung an die Kohlenstoffkette ein Sauerstoffatom,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,
Schwefelatom oder eine Gruppierung ausgewählt aus SO, SO2, NH, N(C) -C4- Alkyl) enthält.Sulfur atom or a moiety selected from SO, SO 2 , NH, N (C) -C 4 alkyl).
A2-X steht außerdem fürA 2 -X also stands for
-(C,-C4-Alkyl)-(CO)-O-, (C,-C4-Alkyl)-(CO)-(NH)-, -(C1-C4-AIlCyIMCO)-[N-(C1-C4- Alkyl)]-, -(C,-C4-Alkyl)-(CO)-S-, -(CrC4-Alkyl)-O-(CO)-, -(C,-C4-Alkyl)-(NH)-(CO)-,- (C 1 -C 4 -alkyl) - (CO) -O-, (C 1 -C 4 -alkyl) - (CO) - (NH) -, - (C 1 -C 4 -alkylCiIMCO) - [N - (C 1 -C 4 - alkyl)] -, - (C, -C 4 alkyl) - (CO) -S-, - (C r C 4 alkyl) -O- (CO) -, - ( C 1 -C 4 -alkyl) - (NH) - (CO) -,
-(C,-C4-Alkyl)-[N-(Ci-C4-Alkyl)]-(CO)-, -(CrC4-Alkyl)-S-(CO)-, -(C2-C8-Alkenyl)-(CO)- O-, -(C2-C8-Alkenyl)-(CO)-(NH)-, -(C2-C8-Alkenyl)-(CO)-[N-(C1-C4-Alkyl)]-, -(C2-C8- Alkenyl)-(CO)-S-, -(C2-C8-Alkenyl)-O-(CO)-(C2-C8-Alkenyl)-(NH)-(CO-)-, -(C1-C4- Alkyl)-[N-(C,-C4-Alkyl)]-(CO)-, -(C2-C8-Alkenyl)-S-(CO)-, -(C1-C4-AIlCyI)-[N-(C1-C4- Alkyl)]-(CO)-, -(C2-C8-Alkenyl)-S-(CO)-, -(CrC4-Alkyl)-(SO2)-(NH)-, -(C2-C8-Alkenyl)-- (C, -C 4 alkyl) - [N- (Ci-C 4 alkyl)] - (CO) -, - (C r C 4 alkyl) -S- (CO) -, - (C 2 -C 8 alkenyl) - (CO) - O-, - (C 2 -C 8 alkenyl) - (CO) - (NH) -, - (C 2 -C 8 alkenyl) - (CO) - [ N- (C 1 -C 4 -alkyl)] -, - (C 2 -C 8 -alkenyl) - (CO) -S-, - (C 2 -C 8 -alkenyl) -O- (CO) - ( C 2 -C 8 alkenyl) - (NH) - (CO -) -, - (C 1 -C 4 - alkyl) - [N- (C, -C 4 alkyl)] - (CO) -, - (C 2 -C 8 -alkenyl) -S- (CO) -, - (C 1 -C 4 -alkyl) - [N- (C 1 -C 4 -alkyl)] - (CO) -, - (C C 2 -C 8 -alkenyl) -S- (CO) -, - (C 1 -C 4 -alkyl) - (SO 2 ) - (NH) -, - (C 2 -C 8 -alkenyl) -
(CO)-S-, -(C2-C8-Alkenyl)-(SO2)-(NH)-, -(C1-C4-AIlCyI)-O-N=C(R9)-, -(CrC8-Alkenyl)-O- N=C(R9)-,(CO) -S-, - (C 2 -C 8 -alkenyl) - (SO 2 ) - (NH) -, - (C 1 -C 4 -alkyl) -ON = C (R 9 ) -, - ( C r C 8 alkenyl) -O- N = C (R 9 ) -,
R9 steht für CrC4-Alkyl oder für Aryl,R 9 is C r C 4 -alkyl or aryl,
A2-X steht weiterhin für ein carbocyclisches gegebenenfalls ein- oder mehrfach ungesättigtes 5,6 oder 7-gliedriges Ringsystem oder für ein gegebenenfalls ein- oder mehrfach ungesättigtesA 2 -X furthermore represents a carbocyclic, optionally mono- or polyunsaturated, 5,6 or 7-membered ring system or an optionally mono- or polyunsaturated one
7-10 gliedriges bicyclisches Ringsystem, das gegebenenfalls ein- oder mehrfach durch7-10-membered bicyclic ring system, which may be mono- or polysubstituted
Sauerstoff, Schwefel, Sulfonyl, Sulfoxyl, Carbonyl, NO, oder gegebenenfalls durch Alkyl substituierten Stickstoff unterbrochen sein kann und gegebenenfalls ein- oder mehrfach substituiert sein kann. Die Anknüpfung dieser Ringsysteme an den Oximsauerstoff erfolgt immer über Kohlenstoff. Die Anknüpfung an den Rest R6 kann über Kohlenstoff oder einOxygen, 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 (Stickstoff oder Schwefel) erfolgen.Heteroatom (nitrogen or sulfur) take place.
R1 steht für Wasserstoff, Nitro, Hydroxy, Amino, Cyano, Fluor, Chlor, Brom, Iod, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Methoxy, Ethoxy, n- oder i-Propoxy substituiertes CrC6-Alkyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkyloxy, C3-C6 Alkenyl, C3-C6 Alkenyl- oxy, C3-C6 Alkinyl, C3-C6 Alkinyloxy, Ci-C6 Alkylcarbonyloxy, C1-C3 Alkylsulfonyl,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,
Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Methoxy, Ethoxy, n- oder i-Propoxy, n-, i-, s- oder t-Butoxy, Methylthio, Ethylthio, n- oder i-Propylthio, n-, i-, s- oder t-Butyl- thio, Methylamino, Ethylamino, n- oder i-Propylamino, n-, i-, s- oder t-Butylamino, Di- methylamino, Diethylamino, Dipropylamino, Acetylamino, Propionylamino, n- oder i-Bu- tyroylamino, Methoximinomethyl, Ethoximinomethyl, Methoximinoethyl oder Ethoxi- minoethyl,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, di-, methylamino, diethylamino, dipropylamino, acetylamino, propionylamino, n- or i-butyrylamino, methoximinomethyl, ethoximinomethyl, methoximinoethyl or ethoximinoethyl,
R2 steht für Wasserstoff, Nitro, Hydroxy, Amino, Cyano, Cyanato, Thiocyanato, Formyl, Halogen, für jeweils gegebenenfalls durch Cyano, Halogen oder durch CpC6-Alkoxy substituiertes Alkyl, Alkoxy, Alkylthio, Alkylsulfinyl, Alkylsulfonyl, Alkylamino, Dialkyl- amino oder Alkylcarbonylamino mit jeweils 1 bis 6 Kohlenstoffatomen in den Alkyl- gruppen, für CpCβ-Alkyl-carbonyl, CpC6-Alkoxy-carbonyl, CpC6-Alkoximinoformyl, Cp Cβ-Alkoximino-acetyl, oder für C2-C6-Alkenyl oder Ca-Cβ-Alkinyl steht,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 CpCβ-alkylcarbonyl, CpC 6 -alkoxycarbonyl, CpC 6 -alkoximinoformyl, Cp Cβ-alkoximino-acetyl, or for C 2 -C 6 -alkenyl or Ca-Cβ-alkynyl,
R3 steht für Wasserstoff, Nitro, Hydroxy, Amino, Cyano, Halogen, für jeweils gegebenenfalls durch Cyano, Halogen oder Ci -Ce- Alkoxy substituiertes Alkyl, Alkoxy, Alkylthio, Alkylamino, Dialkylamino oder Alkylcarbonylamino mit jeweils 1 bis 6 Kohlenstoffatomen in den Alkylgruppen steht,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,
R4 für Wasserstoff, Nitro, Hydroxy, Amino, Cyano, Halogen, für jeweils gegebenenfalls durch Cyano, Halogen oder CpC6- Alkoxy substituiertes Alkyl, Alkoxy, Alkylthio, Alkylamino, Dialkylamino oder Alkylcarbonylamino mit jeweils 1 bis 6 Kohlenstoffatomen in den Alkylgruppen steht,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,
R5 steht für Wasserstoff, geradkettiges oder verzweigtes oder cyclisches Halogenalkanyl oder Halogenalkenyl mit jeweils bis zu 8 Kohlenstoffatomen, Aryl, substituiertes Aryl,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,
R6 steht für eine Alkenyl-Gruppierung, eine Alkinyl-Gruppierung mit jeweils 2 bis 6 Kohlenstoffatomen oder Cycloalkenyl-Gruppierung mit 4 bis 6 Kohlenstoffatomen, welche gegebenenfalls substituiert ist durch mindestens einen Substituenten aus der Reihe Nitro, Cyano, Carboxy, Carbamoyl, Hydroxy, Carbonyl (C=O), Hydroximino (C=N-OH), CpC6- Alkoxy, CpCβ-Alkoxy-carbonyl, CpC6-Alkylamino, Di-(C pC6-alkyl)-amino, CpC6-Al- kylamino-carbonyl, CpC6-Alkoxy-carbonylamino, CrC6-Alkoxy-CpC6-alkoxy, CpC6-AIk- oxyimino, C3-C6-Alkenyloxy, Cß-Cβ-Alkinyloxy, Cs-Cβ-Alkenyloxy-carbonyl, C3-C6- Alkinyloxy-carbonyl, C3-C6-Alkenyloxyimino, C3-C6-Alkinyloxyimino, C3-C6-Cycloalkyl, Furyl, Benzofuryl, Thienyl, Benzothienyl, Isoxazolyl, Benzisoxazolyl, Pyrazolyl, Pyri- dinyl, Pyrimidinyl, Pyrazinyl, Pyridazinyl.R 6 represents an alkenyl grouping, an alkynyl grouping each having 2 to 6 carbon atoms or cycloalkenyl grouping having 4 to 6 carbon atoms which is optionally substituted by at least one substituent selected from nitro, cyano, carboxy, carbamoyl, hydroxy, Carbonyl (C =O), hydroximino (C =N-OH), CpC 6 -alkoxy, CpCβ-alkoxycarbonyl, CpC 6 -alkylamino, di- (C pC 6 -alkyl) -amino, CpC 6 -alkylamino -carbonyl, CpC 6 alkoxy-carbonylamino, C r C 6 alkoxy CpC 6 alkoxy, CpC oxyimino 6 -AIk-, C 3 -C 6 alkenyloxy, C -Cβ ß-alkynyloxy, Cs-Cβ-alkenyloxy carbonyl, C 3 -C 6 -alkynyloxycarbonyl, C 3 -C 6 -alkenyloxyimino, C 3 -C 6 -alkynyloxyimino, C 3 -C 6 -cycloalkyl, furyl, benzofuryl, thienyl, benzothienyl, isoxazolyl, benzisoxazolyl, pyrazolyl, Pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl.
R6 steht außerdem für eine Gruppierung -A3 -Z, wobei A3 für eine Einfachbindung oder für geradkettiges oder verzweigtes und gegebenenfalls durch Halogen oder C3-C6-Cycloalkyl substituiertes Alkandiyl mit 1 bis 6 Kohlenstoffatomen steht undR 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 für gegebenenfalls durch Nitro, Hydroxy, Mercapto, Amino, Formyl, Cyano, Carboxy, Carbamoyl, Halogen, Ci-C6-Alkyl, CrC6-Hydroxyalkyl, CpQ-Halogen- alkyl, CpC6-Alkyl-carbonyl, Ci-C6-Halogenalkyl-carbonyl, CrC6-Alkoxy, CpC6- Hydroxyalkoxy, CpC6-Halogenalkoxy, CpCβ-Alkoxy-carbonyl, CpC6-Halogen- alkoxy-carbonyl, Ci-C6-Alkoxy-Ci-C6-alkyl, CpC6-Halogenalkoxy-CpC6-alkyl, Cp C2-Alkylendioxy, Ci-C2-Haloalkylendioxy, Ci-C6-Alkoxyimino-Ci-C6-alkyl, C2-Q- Alkenyl, C2-C6-Alkenyl-carbonyl, C2-C6-Halogenalkenyl, C2-C6-Halogenalkenyl- carbonyl, C∑-Q-Alkenyloxy-CpQ-alkyl, C2-C6-Halogenalkenyloxy-Ci-C6-alkyl, C2- C6-Alkinyl, C∑-Cδ-Halogenalkinyl, C2-C6-Alkenyloxy, C2-C6-Alkenyloxy-carbonyl, C2-C6-Halogenalkenyloxy, C2-C6-Halogenalkenyloxy-carbonyl, C2-C6-Alkinyloxy, C∑-Cβ-Alkinyloxy-carbonyl, C2-C6-Halogenalkinyloxy, C2-C6-Halogenalkinyloxy- carbonyl, C2-C6-Alkinyloxy-Ci-C6-alkyl, C2-C6-Halogenalkinyloxy-CpC6-alkyl, C3-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, CpCβ-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 -alkyl, C 2 -Q-alkenyl, C 2 -C 6 -alkenyl-carbonyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkenylcarbonyl, C Σ -Q-alkenyloxy-CpQ-alkyl, C 2 -C 6 -haloalkenyloxy-Ci-C 6 - alkyl, C 2 - C 6 alkynyl, C -C Σ δ haloalkynyl, C 2 -C 6 alkenyloxy, C 2 -C 6 alkenyloxy-carbonyl, C 2 -C 6 haloalkenyloxy, C 2 -C 6 - Haloalkenyloxy-carbonyl, C 2 -C 6 -alkynyloxy, C Σ -Cβ-alkynyloxy-carbonyl, C 2 -C 6 -haloalkynyloxy, C 2 -C 6 -haloalkynyloxycarbonyl, C 2 -C 6 -alkynyloxy-Ci-C 6 -alkyl, C 2 -C 6 Haloalkynyloxy-CpC 6 -alkyl, C 3 -
Cg-Cycloalkyl, C3-C8-Cycloalkyl-carbonyl, C3-C8-Cycloalkyl-CrC6-alkyl, C3-C8- Cycloalkyl-Ci-Cβ-alkyl-carbonyl, C3-C8-Cycloalkyloxy, C3-C8-Cycloalkyloxy- carbonyl, C3-C8-Cycloalkyl-Ci-C6-alkoxy, C3-C8-Cycloalkyl-Ci-C6-alkoxy-carbonyl, C3-C8-Cycloalkyloxy-CrC6-alkyl, C3-C8-Cycloalkyloxy-C,-C6-alkoxy, C3-C8-Cyclo- alkyl-Ci-Cβ-alkoxy-Ci-Ce-alkyl, Ci-C6-Alkyl-carbonyl-Ci-C6-alkyl, CrC6-Alkoxy- carbonyl-Ci-C6-alkyl, CrC6-Alkylthio, Ci-C6-Halogenalkylthio, C|-C6-Alkylsulfinyl, Ci-Cβ-Halogenalkylsulfinyl, Ci-Cβ-Alkylsulfonyl, CpCβ-Halogenalkylsulfonyl, C2- C6-Alkenylthio, C2-C6-Halogenalkenylthio, C2-C6-Alkinylthio, C3-C6-Cycloalkylthio, C3-C6-Cycloalkyl-C]-C6-alkylthio, Ci-Cβ-Alkylamino, Ci-Cβ-Alkylamino-carbonyl, Di-(C rC6-alkyl)-amino, Di-(C i-C6-alkyl)-amino-carbonyl, Ci-C6-Alkyl-carbonyl- amino, Ci-Cδ-Halogenalkyl-carbonylamino, Ci-Cβ-Alkoxy-carbonylamino, CpCe- Alkyl-aminocarbonylamino, oder durch Phenyl, Phenyloxy, Benzyl, Benzyloxy, Phenylamino, Benzylamino (wobei jeweils die Phenylgruppen gegebenenfalls durch Nitro, Hydroxy, Mercapto, Amino, Cyano, CpCβ-Alkyl, Ci-Cβ-Halogenalkyl, Ci-Cβ- Alkyl-carbonyl, C2-C6-Alkenyl, C2-C6-Halogenalkenyl, C2-C6-Alkiyl, C2-C6-Cg cycloalkyl, C 3 -C 8 cycloalkyl-carbonyl, C 3 -C 8 cycloalkyl-C r C 6 alkyl, C 3 -C 8 - cycloalkyl-Ci-Cβ-alkyl-carbonyl, C 3 -C 8 -Cycloalkyloxy, C 3 -C 8 -cycloalkyloxycarbonyl, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkoxy, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkoxycarbonyl, C 3 -C 8 -Cycloalkyloxy-C r C 6 -alkyl, C 3 -C 8 -cycloalkyloxy-C, -C 6 -alkoxy, C 3 -C 8 -cycloalkyl-Ci-Cβ-alkoxy-Ci-Ce-alkyl, ci C 6 alkyl-carbonyl-Ci-C 6 alkyl, C r C 6 alkoxy carbonyl-Ci-C 6 alkyl, C r C 6 alkylthio, Ci-C6 haloalkylthio, C | -C 6 - alkylsulfinyl, Ci-Cβ-haloalkylsulfinyl, Ci-Cβ alkylsulfonyl, CpCβ haloalkylsulfonyl, C 2 - C 6 alkenylthio, C 2 -C 6 -Halogenalkenylthio, C 2 -C 6 alkynylthio, C 3 -C 6 cycloalkylthio, C 3 -C 6 -cycloalkyl-C] -C6 alkylthio, Ci-Cβ alkylamino, Ci-Cβ alkylamino-carbonyl, di- (C r C 6 alkyl) amino, di (C iC 6 - alkyl) -amino-carbonyl, Ci-C 6 alkyl-carbonylamino, Ci-C δ haloalkyl-carbonylamino, Ci-Cβ-alkoxy-carbonylamino, CpCe- alkyl aminocarboxylic ylamino, or by phenyl, phenyloxy, benzyl, benzyloxy, phenylamino, benzylamino (in each case the phenyl groups are optionally substituted by nitro, hydroxy, mercapto, amino, cyano, CpCβ-alkyl, Ci-Cβ-haloalkyl, Ci-Cβ-alkyl-carbonyl, C 2 -C 6 alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkenyl, C 2 -C 6 -
Halogenalkinyl, Ci-Cβ-Alkoxy, Ci-Cβ-Halogenalkoxy, C2-C6-Alkenyloxy, C2-C6- Halogenalkenyloxy, C2-C6-Alkinyloxy, Ci-C6-Alkylthio, Ci-C6-Alkylsulfinyl, CpC6- Alkylsulfonyl oder CpC6-Alkoxy-carbonyl substituiert sind) substituiertes Aryl oder monocyclisches oder bicyclisches Heteroaryl mit bis zu 10 Kohlenstoffatomen und mindestens einem Heteroatom aus der Reihe N (Stickstoff, 1 bis 5 N-Atome), O (Sauerstoff, 1 oder 2 O- Atome), Schwefel (1 oder 2 S-Atome) und gegebenenfalls ersatzweise oder zusätzlich einer SO- oder SO2-Gruppierung, und gegebenenfalls zusätzlich einer Carbonyl-Gruppierung (C=O) und/oder einer Thiocarbonyl- Gruppierung (C=S) als Bestandteil des Heterocyclus.Haloalkynyl, Ci-Cβ-alkoxy, Ci-Cβ-haloalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 - haloalkenyloxy, C 2 -C 6 alkynyloxy, Ci-C 6 alkylthio, Ci-C 6 - Alkylsulfinyl, CpC 6 -alkylsulfonyl or CpC 6 -alkoxycarbonyl) substituted aryl or monocyclic or bicyclic heteroaryl having up to 10 carbon atoms and at least one heteroatom selected from N (nitrogen, 1 to 5 N atoms), O (Oxygen, 1 or 2 O atoms), sulfur (1 or 2 S atoms) and optionally substituted or in addition to an SO or SO 2 group , and optionally additionally a carbonyl group (C = O) and / or a Thiocarbonyl grouping (C = S) as part of the heterocycle.
R >6 steht des Weiteren für eine der Gruppierungen:R> 6 also stands for one of the groupings:
A3 steht für eine Bindung oder für eine gegebenenfalls einfach oder mehrfach durchA 3 is a bond or an optionally single or multiple
Halogen oder C3-C8 Cycloalkyl substituierte Ci-Q Alkylenbrücke.Halogen or C 3 -C 8 cycloalkyl substituted Ci-Q alkylene bridge.
M steht für Sauerstoff oder NOR7.M is oxygen or NOR 7 .
R7 steht für Wasserstoff, C,-Ci2Alkyl, C3-C8Cycloalkyl, Q-CeAlkylcarbonyl, C2-C6.R 7 is alkyl 2 represents hydrogen, C, -C, C 3 -C 8 cycloalkyl, Q-CeAlkylcarbonyl, C 2 -C. 6
Alkenyl, C2-C6AIk)TIyI, Aryl, heterocyclyl oder Benzyl, steht, wobei Alkyl, Cycloalkyl, Alkenyl und Alkynyl Reste unsubstituiert sind oder gegebenenfalls ein- bis fünffach mit einem Rest aus der folgender Gruppe substituiert sind: Halogen,-N3, CN, NO2, OH, SH, Ci-C6AIkOXy, Ci-CβHaloalkoxy, C2-C6Alkenyloxy, C2-C6-Haloalkenyloxy, C3-C6- Alkynyloxy, CrCeHaloalkynyloxy, C3-C8CyClOaIlCyI-Ci-C6AIkOXy, CrC6-Alkylcarb- onyl, Cj-CβHaloalkylcarbonyl, Ci-CöAlkoxycarbonyl, Ci-CόAlkylcarbonyl-Ci-CöAlkyl, Ci-CδAlkoxycarbonyl-Ci-CδAlkyl, d-C^kylthio, C2-C6Alkylthio, C3-C6AHCyHyUhIo, C3-C6Cycloalkyl- Ci-CδAlkylthio, C3-C6HaIOaIk)TIyI, Ca-CeHaloalkenylthio, C1-C6HaIo- alkylthio, Ci-C6AIkOXy-Ci-C6AIlCyI, Ci-C6HaIOaIkOXy-Ci-C6AIlCyI, C2-C6AHCeHyIoXy- Ci-C6AIlCyI, C2-C6Haloalkenyloxy-C1-C6Alkyl, C3-C6AIlCyHyIoXy-Ci-C6AIlCyI, NH2,Alkenyl, C 2 -C 6 Alk) TIyI, aryl, heterocyclyl or benzyl, wherein 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, Ci-C 6 -alkoxy, Ci-CβHaloalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 -Haloalkenyloxy, C 3 -C 6 alkynyloxy, CrCeHaloalkynyloxy, C 3 -C 8 CyClOaIlCyI-Ci-C 6 -alkoxy, C r C 6 alkylcarbonyl, Cj-CβHaloalkylcarbonyl, Ci-CöAlkoxycarbonyl, Ci-C ό alkylcarbonyl-Ci-CöAlkyl, Ci-C δ alkoxycarbonyl-Ci-C δ alkyl, dC ^ Kylthio, C 2 -C 6 alkylthio, C 3 -C 6 AHCyHyUhIo, C 3 -C 6 cycloalkyl-Ci-C δ alkylthio, C 3 -C 6 haloalkyl) TIyI, Ca-CeHaloalkenylthio, C 1 -C 6 haloalkylthio , Ci-C 6 -alkoxy-Ci-C 6 AIlCyI, Ci-C 6 HaIOaIkOXy-C 6 AIlCyI, C 2 -C 6 AHCeHyIoXy- Ci-C 6 AIlCyI, C 2 -C 6 haloalkenyloxy-C 1 -C 6 Alkyl, C 3 -C 6 Al 1 -CyHyIoXy-Ci-C 6 AlCl y, NH 2 ,
NHQ-CβAlkenyl, QrCeHaloalkenyl, C3-C6AIlCyHyI, C3-C8Cycloalkyl, C3-C8Cycloalkyl- Ci-C6AIlCyI, Ci-C6AIkOXy, Ci-CöHaloalkoxy, Ca-CeAlkenyloxy, C2-C6Haloalkenyloxy, C3-C6AIk)TIyIoXy, C3-C6HaIOaIk)TIyIoXy, C3-C8CyClOaIlCyI-Ci-C6AIkOXy, Ci-C6AIlCyI- carbonyl, CpCβHaloalkyl- Carbonyl, Ci-CδAlkoxycarbonyl, Cj-CδAlkylcarbonyl-Ci-Cö- Alkyl, Ci-CδAlkoxycarbonyl- Ci-C6AIlCyI, Ci-CöAlkylthio, C2-C6AIkCHyItHiO, C3-C6Al- kynylthio, C3-C6CyClOaUCyI-Ci-C6AUCyItHiO, C3-C6HaIOaIk)TIyI, C2-C6Haloalkenylthio, Ci-CeHaloalkylthio, C1-C6AIkOXy-C1-C6AIlCyI, C1-C6HaIOaIkOXy-C-C6AIlCyI, C2-C6Al- kenyloxy-Ci-CβAlkyl. C∑-CöHaloalkenyloxy-Ci-CδAlkyl, C3-C6AUCyHyIoXy-Ci-C6AIlCyI, N(Cj-C6AIlCyI)2, wobei die zwei Alkylgruppen unabhängig voneinander Ci-C6Al- kylcarbonylamino, CpCβHaloalkylcarbonylamino, Ci-CöAlkoxycarbonylamino und Ci-CβAlkylaminocarbonylamino sein können.NHQ-CβAlkenyl, QrCeHaloalkenyl, C 3 -C 6 AIlCyHyI, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkyl, Ci-C 6 AIlCyI, Ci-C 6 -alkoxy, Ci-CöHaloalkoxy, Ca-CeAlkenyloxy, C 2 - C 6 haloalkenyloxy, C 3 -C 6 alkyl), TIyIoXy, C 3 -C 6 haloalkyl), TIyIoXy, C 3 -C 8 CyClOAIlCyI-Ci-C 6 AIkOXy, Ci-C 6 AIlCyI- carbonyl, CpCβHaloalkyl- carbonyl, Ci-C δ alkoxycarbonyl, Cj-C δ alkylcarbonyl-Ci-COE alkyl, Ci-C δ alkoxycarbonyl Ci-C 6 AIlCyI, Ci-CöAlkylthio, C 2 -C 6 AIkCHyItHiO, C 3 -C 6 Al kynylthio, C 3 - C 6 CyClOaUCyI-Ci-C 6 AUCyItHiO, C 3 -C 6 haloalkyl) TIyI, C 2 -C 6 haloalkenylthio, C 1 -C 6 haloalkylthio, C 1 -C 6 alkoxy C 1 -C 6 alkyl, C 1 -C 6 haloalkoxy -CC 6 AIlCyI, C 2 -C 6 alkenyloxy-Ci-CβAlkyl. C Σ -CöHaloalkenyloxy-C δ 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, CpCβHaloalkylcarbonylamino, Ci-C ö Alkoxycarbonylamino and Ci-CβAlkylaminocarbonylamino can be.
W steht für *C(R32R33) oder *C(R32R33)C(R34R35), wobei der Stern „*"W stands for * C (R 32 R 33 ) or * C (R 32 R 33 ) C (R 34 R 35 ), where the star "*"
die Anbindung an Sauerstoff bedeutet und worin R32 bis R35 jeweils unabhängig voneinander für Halogen, Ci-C4Alkyl, Ci-C4Alkoxy(CrC4)Alkyl oder HaIo(Ci -C4) Alkyl stehen.the bond to oxygen and wherein 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 kann Werte von 0 bis 3 annehmen,n can take values from 0 to 3,
R8 steht jeweils unabhängig voneinander für Wasserstoff, Halogen, HaIo(Ci-C4) Alkyl, C3-Each R 8 is independently hydrogen, halogen, halo (C 1 -C 4 ) alkyl, C 3 -
C6Cycloalkyl, C2-C5Alkenyl, C2-C5Alkynyl, C,-C4Haloalkyl, CrC4Alkoxy, C-C4HaIo- alkoxy, C,-C4Alkylthio, CrC4Haloalkylthio, CrC4Alkylsulfonyl, CrC4Haloalkylsulfonyl,C 6 cycloalkyl, C 2 -C 5 alkenyl, C 2 -C 5 alkynyl, C, -C 4 haloalkyl, C r C 4 alkoxy, CC 4 haloalkoxy, C, -C 4 alkylthio, C r C 4 haloalkylthio, C r C 4 alkylsulfonyl, C r C 4 haloalkylsulfonyl,
Nitro, Cyano, Aryl, Alkylcarbonylamino, Arylcarbonylamino und Ci-CψAlkoxycarb- onylamino.Nitro, cyano, aryl, alkylcarbonylamino, arylcarbonylamino and Ci-CψAlkoxycarb- onylamino.
R10 und R11 stehen jeweils unabhängig voneinander für Wasserstoff, Halogen, Hydroxy, (Cr C4) Alkyl, HaIo(C1-C4) Alkyl oder (C1-C4) Alkoxy oderR 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
zusammen für Carbonyl, für -0-CH2-CH2-O-, S-CH2-CH2-S, Ketal, Thioketal oder ein Oxim bildend in der Form NOR12, wobeitogether for carbonyl, for -O-CH 2 -CH 2 -O-, S-CH 2 -CH 2 -S, ketal, thioketal or an oxime in the form of NOR 12 , wherein
R12 für (CrC3)Alkyl, (C1-C3)AIkOXy(C1-C3) Alkyl, Aryl-(CrC3)Alkyl, C2-C4Alkenyl-(C,- C3)Alkyl, HaIo(C2-C4) Alkenyl-(C1 -C3)AIlCyI, di(CrC3)Alkylphosphonat, Formyl, (C,- C3)Alkylcarbonyl, HaIo(C1- C3)Alkylcarbonyl, (Ci-C3)Alkoxy(C|-C3)Alkylcarbonyl, Arylcarbonyl und (CrC3)Alkylsulfonyl steht.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 | -C 3) alkylcarbonyl, arylcarbonyl and (C r C 3) alkylsulphonyl.
Bevorzugte Substituenten bzw. bevorzugte Bereiche der in den oben und nachstehend aufgeführten Formeln vorhandenen Reste werden im Folgenden definiert.Preferred substituents or preferred ranges of the radicals present in the formulas given above and below are defined below.
A1 steht bevorzugt für eine der folgenden Gruppierungen: -CH2-CH=CCl2, -CH2-CH=CBr2, -CH2-CH=CClF, -CH2-CH=CBrCl, -CH2-CH=CBrF.A 1 preferably represents one of the following groupings: -CH 2 -CH = CCl 2 , -CH 2 -CH = CBr 2 , -CH 2 -CH = CClF, -CH 2 -CH = CBrCl, -CH 2 -CH = CBrF.
A1 steht besonders bevorzugt für eine der folgenden Gruppierungen: -CH2-CH=CCl2, -CH2-CH=CBr2, -CH2-CH=CBrCl.A 1 particularly preferably represents one of the following groupings: -CH 2 -CH = CCl 2 , -CH 2 -CH = CBr 2 , -CH 2 -CH = CBrCl.
A1 steht ganz besonders bevorzugt für die Gruppierung -CH2-CH=CCl2. A2-X steht bevorzugt für ein geradkettiges oder verzweigtes Alkandiyl oder Alkendiyl mit jeweils bis zu 8 Kohlenstoffatomen, welches gegebenenfalls innerhalb der Kohlenstoffkette ein Sauerstoffatom, Schwefelatom oder eine Gruppierung ausgewählt aus SO, SO2, NH, N(C,-C4-Alkyl) enthält sowie fürA 1 very particularly preferably represents the grouping -CH 2 -CH = CCl 2 . 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
-(C1-C4-AIlCyI)-(CO)-O-, -(CrC4-Alkyl)-(CO)-(NH)-, -(C1-C4-AIlCyI)-(CO)-[N-(C1-C4-- (C 1 -C 4 -alkyl) - (CO) -O-, - (C r C 4 alkyl) - (CO) - (NH) -, - (C 1 -C 4 -alkyl) - (CO ) - [N- (C 1 -C 4 -
Alkyl)]-, -(CrC4-Alkyl)-(CO)-S-, (C2-C8-Alkenyl)-(CO)-O-, -(C2-C8-Alkenyl)-(CO)-(NH)-, -(C2-C8-AIkCHyI)-(CO)-[N-(C1-C4-AIlCyI)]-, -(C2-C8 '-Alkenyl)-(CO)-S, Piperidyl oder Piperazinyl, -(C1-C4-AIlCyI)-O-N=C(R9)-, -(C,-C6-Alkenyl)-O-N=C(R9)-, worinAlkyl)] -, - (C r C 4 alkyl) - (CO) -S-, (C 2 -C 8 alkenyl) - (CO) -O-, - (C 2 -C 8 alkenyl) - (CO) - (NH) -, - (C 2 -C 8 -alkyl) - (CO) - [N- (C 1 -C 4 -alkyl) -, - (C 2 -C 8 ' -alkenyl) - (CO) -S, piperidyl or piperazinyl, - (C 1 -C 4 -alkyl) -ON = C (R 9 ) -, - (C 1 -C 6 -alkenyl) -ON = C (R 9 ) - in which
R9 bevorzugt für Methyl oder für Aryl steht.R 9 is preferably methyl or aryl.
A2-X steht besonders bevorzugt für ein geradkettiges oder verzweigtes Alkandiyl oder Alkendiyl mit jeweils bis zu 8 Kohlenstoffatomen, welches gegebenenfalls innerhalb der Kohlenstoffkette ein Sauerstoffatom enthält sowie fürA 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
-(C1-C4-AIlCyI)-(CO)-O-, -(CrC4-Alkyl)-(CO)-(NH>, -(C1-C4-AIlCyI)-(CO)-[N-(C1-C4- Alkyl)]-, -(C1-C4-AIlCyIMCO)-S-, (C2-C8-Alkenyl)-(CO)-O-, -(C2-C8-Alkenyl)-(CO)-(NH)-, -(C2-C8-Alkenyl)-(CO)-[N-(CrC4-Alkyl)]-, -(C2-C8-Alkenyl)-(CO)-S, Piperidyl oder- (C 1 -C 4 -alkyl) - (CO) -O-, - (C r C 4 alkyl) - (CO) - (NH>, - (C 1 -C 4 -alkyl) - (CO) - [N- (C 1 -C 4 -alkyl)] -, (C 1 -C 4 -alkylCMIMCO) -S-, (C 2 -C 8 -alkenyl) - (CO) -O-, - (C 2 -C 8 alkenyl) - (CO) - (NH) -, - (C 2 -C 8 alkenyl) - (CO) - [N- (C r C 4 -alkyl)] -, - (C 2 -C 8 alkenyl) - (CO) -S, piperidyl or
Piperazinyl, -(C,-C4-Alkyl)-O-N=C(R9)-, -(C1-C6-AIk6HyI)-O-N=C(R9)-, worinPiperazinyl, - (C, -C 4 alkyl) -ON = C (R 9 ) -, - (C 1 -C 6 -Alk 6 HyI) -ON = C (R 9 ) -, in which
R9 besonders bevorzugt für Methyl steht.R 9 particularly preferably represents methyl.
A2-X steht ganz besonders bevorzugt für ein geradkettiges oder verzweigtes Alkandiyl mit bis zu 8 Kohlenstoffatomen, welches gegebenenfalls innerhalb der Kohlenstoffkette ein Sauerstoffatom enthält sowie für -(CrC4-Alkyl)-(CO)-O-, -(C1-C4-AIlCyI)-(CO)-(NH)- oderA 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
Piperidyl.Piperidyl.
Innerhalb der oben genannten Definition der optionalen BrückeWithin the above definition of the optional bridge
sind folgende Bedeutungen der Reste R21 und R22 bevorzugt oder besonders bevorzugt:the following meanings of the radicals R 21 and R 22 are preferred or particularly preferred:
R21 und R22 stehen unabhängig voneinander bevorzugt für Wasserstoff, Nitro, Hydroxy, Amino, Cyano, Cyanato, Thiocyanato, Formyl, Halogen oder Methyl,R 21 and R 22 independently of one another preferably represent hydrogen, nitro, hydroxyl, amino, cyano, cyanato, thiocyanato, formyl, halogen or methyl,
R21 und R22 stehen besonders bevorzugt für Wasserstoff. R1 steht bevorzugt für Wasserstoff, Nitro, Hydroxy, Cyano, Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-Propyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio, Ethylthio, n- oder i-Propylthio, Methylamino, Ethylamino, n- oder i-Propylamino, Dimethylamino oder für die Gruppierung -O-A1, wobei A1 eine der vorstehend angebenenen Bedeutungen hat.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.
R1 steht besonders bevorzugt für Wasserstoff, Nitro, Hydroxy, Cyano, Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-Propyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio, Ethylthio, n- oder i-Propylthio, Methylamino, Ethylamino, n- oder i-Propylamino oder Dimethylamino.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.
R1 steht ganz besonders bevorzugt für Wasserstoff, Methyl, Ethyl, Methoxy, Ethoxy oder Fluor, Chlor, Brom.R 1 very particularly preferably represents hydrogen, methyl, ethyl, methoxy, ethoxy or fluorine, chlorine, bromine.
R2 steht bevorzugt für Wasserstoff, Nitro, Cyano, Cyanato, Thiocyanato, Formyl, Halogen, für jeweils gegebenenfalls durch Cyano, Halogen oder Ci-C5-Alkoxy substituiertes Alkyl, Alkoxy, Alkylthio, Alkylamino, Dialkylamino oder Alkylcarbonylamino mit jeweils 1 bis 5 Kohlenstoffatomen in den Alkylgruppen, für für Ci-C5-Alkyl-carbonyl, Ci-Cs-Alkoxy- carbonyl, Ci-C5-Alkoximinoformyl, Ci-Cs-Alkoximino-acetyl, oder für C2-C5-Alkenyl oderR 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
C2-C5-Alkinyl.C 2 -C 5 alkynyl.
R2 steht besonders bevorzugt für Wasserstoff, Nitro, Cyano, Cyanato, Thiocyanato, Formyl, Fluor, Chlor, Brom, Iod, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Methoxy, Ethoxy, n- oder i-Propoxy substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t- Butyl, Methoxy, Ethoxy, n- oder i-Propoxy, n-, i-, s- oder t-Butoxy, Methylthio, Ethylthio, n- oder i-Propylthio, n-, i-, s- oder t-Butylthio, Methylamino, Ethylamino, n- oder i-Propyl- amino, n-, i-, s- oder t-Butylamino, Dimethylamino, Diethylamino, Acetylamino, Propionylamino, n- oder i-Butyroylamino, Acetyl, Propionyl, n- oder i-Butyroyl, Methoxy- carbonyl, Ethoxycarbonyl, n-oder i-Propoxycarbonyl, Methoximinoformyl, Ethoximino- formyl, Methoximinoacetyl oder Ethoximinoacetyl.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-butylamino, dimethylamino, diethylamino, acetylamino , Propionylamino, n- or i-butyroylamino, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methoximinoformyl, ethoximi- formyl, methoximinoacetyl or ethoximinoacetyl.
R2 steht ganz besonders bevorzugt für Wasserstoff, Cyano, Fluor, Chlor, Brom oder Iod.R 2 very particularly preferably represents hydrogen, cyano, fluorine, chlorine, bromine or iodine.
R2 steht am meisten bevorzugt für Wasserstoff, Fluor, Chlor oder Brom.R 2 most preferably represents hydrogen, fluorine, chlorine or bromine.
R3 steht bevorzugt für Wasserstoff, Nitro, Halogen, für jeweils gegebenenfalls durch Cyano, Halogen oder C]-C5-Alkoxy substituiertes Alkyl, Alkoxy, Alkylthio oder Alkylamino mit jeweils 1 bis 5 Kohlenstoffatomen in den Alkylgruppen. R3 steht besonders bevorzugt für Wasserstoff, Nitro, Fluor, Chlor, Brom, Iod, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Methoxy, Ethoxy, n- oder i-Propoxy substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Methoxy, Ethoxy, n- oder i-Propoxy, n-, i-, s- oder t-Butoxy, Methylthio, Ethylthio, n- oder i-Propylthio, n-, i-, s- oder t-Butyl- thio, Methylamino, Ethylamino, n- oder i-Propylamino, n-, i-, s- oder t-Butylamino.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.
R3 steht ganz besonders bevorzugt für Wasserstoff, Cyano, Fluor, Chlor, Brom, Methyl, Ethyl, Methoxy oder Ethoxy.R 3 very particularly preferably represents hydrogen, cyano, fluorine, chlorine, bromine, methyl, ethyl, methoxy or ethoxy.
R4 steht bevorzugt für Wasserstoff, Nitro, Halogen, für jeweils gegebenenfalls durch Cyano, Halogen oder Ci-C5-Alkoxy substituiertes Alkyl, Alkoxy, Alkylthio oder Alkylamino mit jeweils 1 bis 5 Kohlenstoffatomen in den Alkylgruppen.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.
R4 steht besonders bevorzugt für Wasserstoff, Nitro, Fluor, Chlor, Brom, Iod, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Methoxy, Ethoxy, n- oder i-Propoxy substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Methoxy, Ethoxy, n- oder i-Propoxy, n-, i-, s- oder t-Butoxy, Methylthio, Ethylthio, n- oder i-Propylthio, n-, i-, s- oder t-Butyl- thio, Methylamino, Ethylamino, n- oder i-Propylamino, n-, i-, s- oder t-Butylamino.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.
R4 steht ganz besonders bevorzugt für Wasserstoff, Cyano, Fluor, Chlor oder Brom.R 4 very particularly preferably represents hydrogen, cyano, fluorine, chlorine or bromine.
R5 steht bevorzugt für eine Alkanyl-Gruppierung oder Alkinyl-Gruppierung mit jeweils 2 bisR 5 preferably represents an alkanyl grouping or alkynyl grouping with 2 to
5 Kohlenstoffatomen oder Cycloalkanyl-Gruppierung mit 4 bis 6 Kohlenstoffatomen, welche jeweils mindestens einen Substituenten aus der Reihe Nitro, Cyano, Carboxy, Carbamoyl, Hydroxy, Carbonyl (C=O), Hydroximino (C=N-OH), C,-C5-Alkoxy, C1-C5-5 carbon atoms or cycloalkanyl grouping having 4 to 6 carbon atoms, each having at least one substituent selected from nitro, cyano, carboxy, carbamoyl, hydroxy, carbonyl (C = O), hydroximino (C = N-OH), C, -C 5- alkoxy, C 1 -C 5 -
Alkoxy-carbonyl, Ci-Cs-Alkylamino, Di-(C i-C4-alkyl)-amino, Ci-Cs-Alkylamino-carbonyl, Ci-Cs-Alkoxy-carbonylamino, Ci-Cs-Alkoxy-CpCs-alkoxy, Ci-Cs-Alkoxyimino, C3-C5- Alkenyloxy, Ca-Cs-Alkinyloxy, Cs-Cs-Alkenyloxy-carbonyl, Cs-Cs-Alkinyloxy-carbonyl, C3-C5-Alkenyloxyimino, C3-C5-Alkinyloxyimino, C3-C6-Cycloalkyl enthalten.Alkoxycarbonyl, C 1 -C 8 -alkylamino, di (C 1 -C 4 -alkyl) amino, C 1 -C 8 -alkylamino-carbonyl, C 1 -C 8 -alkoxycarbonylamino, C 1 -C 8 -alkoxy-C 1 -C 5 -alkoxy, Cs-alkoxyimino, C 3 -C 5 -alkenyloxy, Ca-Cs-alkynyloxy, Cs-Cs-alkenyloxy-carbonyl, Cs-Cs-alkynyloxy-carbonyl, C 3 -C 5 -alkenyloxyimino, C 3 -C 5 -alkynyloxyimino, C 3 -C 6 cycloalkyl.
R5 steht besonders bevorzugt für Wasserstoff, Methyl, i-Propyl, Cyclopropy oder Cyclohexyl.R 5 particularly preferably represents hydrogen, methyl, isopropyl, cyclopropyl or cyclohexyl.
R5 steht ganz besonders bevorzugt für Methyl,R 5 is very particularly preferably methyl,
R6 steht bevorzugt für eine Alkenyl-Gruppierung oder Alkinyl-Gruppierung mit jeweils 2 bisR 6 preferably represents an alkenyl grouping or alkynyl grouping with 2 to
6 Kohlenstoffatomen oder Cycloalkenyl-Gruppierung mit 4 bis 6 Kohlenstoffatomen, welche gegebenenfalls substituiert ist durch mindestens einen Substituenten aus der Reihe Nitro, Cyano, Carboxy, Carbamoyl, Hydroxy, Carbonyl (C=O), Hydroximino (C=N-OH),6 carbon atoms or cycloalkenyl grouping having 4 to 6 carbon atoms which is optionally substituted by at least one substituent selected from nitro, cyano, carboxy, carbamoyl, hydroxy, carbonyl (C =O), hydroximino (C =N-OH),
Ci-C4-Alkoxy, Ci-GrAlkoxy-carbonyl, Ci-C4-Alkylamino, Di-(Ci-C4-alkyl)-amino, Q-C4- Alkylamino-carbonyl, Ci-C4-Alkoxy-carbonylamino, Ci-C4-Alkoxy-Ci-C6-alkoxy, C1-C4- Alkoxyimino, C3-C4-Alkenyloxy, C3-C4-Alkinyloxy, C3-C4-Alkenyloxy-carbonyl, C3-C4- Alkinyloxy-carbonyl, C3-C4-Alkenyloxyimino, C3-C4-Alkinyloxyimino, C3-C6-Cycloalkyl, Furyl, Benzofuryl, Thienyl, Benzothienyl, Isoxazolyl, Benzisoxazolyl, Pyrazolyl, Pyridinyl, Pyrimidinyl, Pyrazinyl, Pyridazinyl,C 1 -C 4 -alkoxy, C 1 -C 6 -alkoxy-carbonyl, C 1 -C 4 -alkylamino, di- (C 1 -C 4 -alkyl) -amino, QC 4 - Alkylamino-carbonyl, Ci-C 4 -alkoxy-carbonylamino, Ci-C 4 alkoxy-C 6 -alkoxy, C 1 -C 4 - alkoxyimino, C 3 -C 4 alkenyloxy, C 3 -C 4 alkynyloxy , C 3 -C 4 alkenyloxy-carbonyl, C 3 -C 4 -alkynyloxycarbonyl, C 3 -C 4 -alkenyloxyimino, C 3 -C 4 -alkynyloxyimino, C 3 -C 6 -cycloalkyl, furyl, benzofuryl, thienyl , Benzothienyl, isoxazolyl, benzisoxazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl,
Bevorzugt oder besonders bevorzugt sind auch die oben genannten Alternativen in der Definition von R6, in denen die Reste A3, Z, M, R7, W, n, R8, R10 und R11 die nachfolgenden bevorzugten oder besonders bevorzugten Bedeutungen haben.The abovementioned alternatives in the definition of 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.
A3 steht bevorzugt für eine Einfachbindung oder für geradkettiges oder verzweigtes und gege- benenfalls durch Halogen oder C3-C6-Cycloalkyl substituiertes Alkandiyl mit 1 bis 6A 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
Kohlenstoffatomen,Carbon atoms,
A3 steht besonders bevorzugt für eine Einfachbindung oder für jeweils gegebenenfalls durchA 3 particularly preferably stands for a single bond or for each case optionally
Fluor, Chlor, Brom, Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl substituiertesFluorine, chlorine, bromine, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl substituted
Methylen, Ethan-l,l-diyl (Ethyliden), Ethan-l,2-diyl (Dimethylen), Propan-l,l-diyl (Propyliden), Propan-l,2-diyl, Propan-l,3-diyl (Trimethylen), Butan- 1,1-diyl (Butyliden) oder Butan- 1,4-diyl (Tetramethylen),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),
A3 steht ganz besonders bevorzugt für eine Einfachbindung oder für Methylen,A 3 very particularly preferably represents a single bond or methylene,
Z bevorzugt für jeweils gegebenenfalls durch Nitro, Hydroxy, Amino, Formyl, Cyano, Carboxy, Carbamoyl, Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t- Butyl, Fluormethyl, Chlormethyl, Difluormethyl, Dichlormethyl, Trifluormethyl,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,
Trichlormethyl, Fluorethyl, Chlorethyl, Difluorethyl, Dichlorethyl, Chlorfluorethyl, Trifluorethyl, Trichlorethyl, Chlordifluorethyl, Fluorpropyl, Chloφropyl, Difluorpropyl, Dichlorpropyl, Trifluorpropyl, Fluor-i-propyl, Difluor-i-propyl, Trifluor-i-propyl, Tetra- fluor-i-propyl, Pentafluor-i-propyl, Methoxy, Ethoxy, n- oder i-Propoxy, Fluormethoxy, Difluormethoxy, Trifluormethoxy, Fluordichlormethoxy, Chlordifluormethoxy,Trichloromethyl, fluoroethyl, chloroethyl, difluoroethyl, dichloroethyl, chlorofluoroethyl, trifluoroethyl, trichloroethyl, chlorodifluoroethyl, fluoropropyl, chloropropyl, difluoropropyl, dichloropropyl, trifluoropropyl, fluoro-i-propyl, difluoro-i-propyl, trifluoro-i-propyl, tetrafluoro- i-propyl, pentafluoro-i-propyl, methoxy, ethoxy, n- or i-propoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, fluorodichloromethoxy, chlorodifluoromethoxy,
Fluorethoxy, Chlorethoxy, Difluorethoxy, Dichlorethoxy, Trifluorethoxy, Fluorpropoxy, Methoxycarbonyl, Ethoxycarbonyl, Fluorethoxycarbonyl, Chlorethoxycarbonyl, Methoxy- methyl, Ethoxymethyl, n- oder i-Propoxymethyl, Methoxyethyl, Ethoxyethyl, n- oder i- Propoxyethyl, Ethenyl, Propenyl, Butenyl, Fluorethenyl, Chlorethenyl, Difluorethenyl, Dichlorethenyl, Trifluorethenyl, Trichlorethenyl, Propenyloxymethyl, Butenyloxymethyl,Fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, trifluoroethoxy, fluoropropoxy, methoxycarbonyl, ethoxycarbonyl, fluoroethoxycarbonyl, chloroethoxycarbonyl, methoxymethyl, ethoxymethyl, n- or i-propoxymethyl, methoxyethyl, ethoxyethyl, n- or i-propoxyethyl, ethenyl, propenyl, butenyl, Fluoroethenyl, chloroethenyl, difluoroethenyl, dichloroethenyl, trifluoroethenyl, trichloroethenyl, propenyloxymethyl, butenyloxymethyl,
Propenyloxyethyl, Butenyloxyethyl, Ethinyl, Propinyl, Butinyl, Propenyloxy, Butenyloxy, Fluorpropenyloxy, Chlorpropenyloxy, Fluorbutenyloxy, Chlorbutenyloxy, Propenyloxy- carbonyl, Butenyloxycarbonyl, Propinyloxy, Butinyloxy, Propinyloxycarbonyl, Butinyl- .Propenyloxyethyl, butenyloxyethyl, ethynyl, propynyl, butynyl, propenyloxy, butenyloxy, fluoropropenyloxy, chloropropenyloxy, fluorobutenyloxy, chlorobutenyloxy, propenyloxycarbonyl, butenyloxycarbonyl, propynyloxy, butynyloxy, propynyloxycarbonyl, butynyl ,
oxycarbonyl, Propinyloxymethyl, Butinyloxymethyl, Propinyloxyethyl, Butinyloxyethyl, Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclopropylcarbonyl, Cyclobutylcarbonyl, Cyclo- pentylcarbonyl, Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl, Cyclohexylmethyl, Cyclopropylmethylcarbonyl, Cyclobutylmethylcarbonyl, Cyclopentyl- methylcarbonyl, Cyclopropyloxy, Cyclobutyloxy, Cyclopentyloxy, Cyclohexyloxy,oxycarbonyl, propynyloxymethyl, butynyloxymethyl, propynyloxyethyl, butynyloxyethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethylcarbonyl, cyclobutylmethylcarbonyl, cyclopentylmethylcarbonyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy,
Cyclopropyloxycarbonyl, Cyclobutyloxycarbonyl, Cyclopentyloxycarbonyl,Cyclopropyloxycarbonyl, cyclobutyloxycarbonyl, cyclopentyloxycarbonyl,
Cyclohexyloxycarbonyl, Cyclopropylmethoxy, Cyclobutylmethoxy, Cyclopentylmethoxy, Cyclohexylmethoxy, Cyclopropylmethoxycarbonyl, Cyclobutylmethoxycarbonyl, Cyclo- pentylmethoxycarbonyl, Cyclohexylmethoxycarbonyl, Cyclopropylmethoxymethyl, Cyclo- butylmethoxymethyl, Cyclopentylmethoxymethyl, Cyclopropyloxymethoxy, Cyclo- butyloxymethoxy, Cyclopentyloxymethoxy, Acetylmethyl, Propionylmethyl, n- oder i- Butyroylmethyl, Acetylethyl, Propionylethyl, Methoxycarbonylmethyl, Ethoxycarbonyl- methyl, n- oder i-Propoxycarbonylmethyl, Methoxycarbonylethyl, Ethoxycarbonylethyl, n- oder i-Propoxycarbonylethyl, Methylthio, Ethylthio, n- oder i-Propylthio, Difluormethyl- thio, Trifluormethylthio, Chlordifluormethylthio, Methylsulfinyl, Ethylsulfinyl, Trifluor- methylsulfϊnyl, Methylsulfonyl, Ethylsulfonyl, Trifluormethylsulfonyl, Propenylthio, Butenylthio, Fluoφropenylthio, Chlorpropenylthio, Fluorbutenylthio, Chlorbutenylthio, Propinylthio, Butinylthio, Cyclopropylthio, Cyclobutylthio, Cyclopentylthio, Cyclohexylthio, Cyclopropylmethylthio, Cyclobutylmethylthio, Cyclopentylmethylthio, Methylamino, Ethylamino, n- oder i-Propylamino, Methylaminocarbonyl, Ethylamino- carbonyl, n- oder i-Propylaminocarbonyl, Dimethylamino, Diethylamino, Dimethylamino- carbonyl, Diethylaminocarbonyl, Acetylamino, Propionylamino, n- oder i-Butyroylamino, Methoxycarbonylamino, Ethoxycarbonylamino, n- oder i-Propoxycarbonylamino, Methyl- aminocarbonylamino, Ethylaminocarbonylamino, n- oder i-Propylaminocarbonylamino, oder durch Phenyl, Phenyloxy, Benzyl, Benzyloxy, Phenylamino, Benzylamino (wobei jeweils die Phenylgruppen gegebenenfalls durch Nitro, Hydroxy, Mercapto, Amino, Cyano, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Trifluormethyl, Methoxy, Ethoxy, n- oder i-Propoxy, Difluormethoxy, Trifluormethoxy, Fluorethoxy, Difluorethoxy, Trifluorethoxy, Propenyloxy, Butenyloxy, Propinyloxy, Butinyloxy, Propinylthio, Butinyl- thio, Methylsulfinyl, Ethylsulfinyl, Methylsulfonyl, Ethylsulfonyl, Methoxycarbonyl,Cyclohexyloxycarbonyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, Cyclopropylmethoxycarbonyl, Cyclobutylmethoxycarbonyl, cyclo pentylmethoxycarbonyl, Cyclohexylmethoxycarbonyl, Cyclopropylmethoxymethyl, cyclo butylmethoxymethyl, Cyclopentylmethoxymethyl, Cyclopropyloxymethoxy, cyclo butyloxymethoxy, Cyclopentyloxymethoxy, acetylmethyl, propionylmethyl, n- or i- Butyroylmethyl, acetylethyl, Propionylethyl , Methoxycarbonylmethyl, ethoxycarbonylmethyl, n- or i-propoxycarbonylmethyl, methoxycarbonylethyl, ethoxycarbonylethyl, n- or i-propoxycarbonylethyl, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, methylsulfinyl, ethylsulfinyl, trifluoro- methylsulfϊnyl, methylsulfonyl, ethylsulfonyl, trifluoromethylsulfonyl, propenylthio, butenylthio, fluoφropenylthio, chloropropenylthio, fluorobutenylthio, chlorobutenylthio, propynylthio, butynylthio, cyclopropylthio, cyclobutylthio, cyclopentylt hio, cyclohexylthio, cyclopropylmethylthio, cyclobutylmethylthio, cyclopentylmethylthio, methylamino, ethylamino, n- or i-propylamino, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylamino, diethylamino, dimethylaminocarbonyl, diethylaminocarbonyl, acetylamino, propionylamino, n- or i-butyroylamino, methoxycarbonylamino, ethoxycarbonylamino, n- or i-propoxycarbonylamino, methylaminocarbonylamino, ethylaminocarbonylamino, n- or i-propylaminocarbonylamino, or by phenyl, phenyloxy, benzyl, benzyloxy, phenylamino, benzylamino (in each case the phenyl groups being optionally substituted by nitro , Hydroxy, mercapto, amino, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, Fluoroethoxy, difluoroethoxy, trifluoroethoxy, propenyloxy, butenyloxy, propynyloxy, butynyloxy, propynylthio, butynylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methoxycarbonyl,
Ethoxycarbonyl, n- oder i-Propoxycarbonyl substituiert sind) substituiertes, mono- cyclisches Heteroaryl mit bis zu 5 Kohlenstoffatomen und mindestens einem Heteroatom aus der Reihe N (Stickstoff, 1 bis 4 N-Atome), O (Sauerstoff, 1 O-Atom), Schwefel (1 S- Atom) und gegebenenfalls ersatzweise oder zusätzlich einer SO- oder SO2-Gruppierung, und gegebenenfalls zusätzlich einer Carbonyl-Gruppierung (C=O) und/oder einer Thio- carbonyl-Gruppierung (C=S) als Bestandteil des Heterocyclus steht, wobei als Heteroaryl- Gruppierungen insbesondere Pyrrolyl, Pyrazolyl, Imidazolyl, Triazolyl, Tetrazolyl, Furyl, Thienyl, Oxazolyl, Isoxazolyl, Thiazolyl, Isothiazolyl, Oxadiazolyl, Thiadiazolyl, Pyridinyl, Pyrimidinyl, Pyridazinyl, Pyrazinyl, ganz besonders aber Tetrazolyl genannt seien.Ethoxycarbonyl, n- or i-propoxycarbonyl) substituted, monocyclic heteroaryl having up to 5 carbon atoms and at least one heteroatom from the series N (nitrogen, 1 to 4 N atoms), O (oxygen, 1 O atom) , Sulfur (1 S atom) and optionally substituted or in addition to an SO or SO 2 group , and optionally in addition a carbonyl group (C = O) and / or a thiocarbonyl group (C = S) as a constituent of the heterocycle, where as heteroaryl In particular, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, but especially tetrazolyl, may be mentioned.
M steht bevorzugt für Sauerstoff,M is preferably oxygen,
R7 steht bevorzugt für Wasserstoff; C|-C6Alkyl, C3-C6Cycloalkyl, Ci-C4Alkylcarbonyl, C2- C4Alkenyl, C2-C4Alkynyl, Aryl, heterocyclyl oder Benzyl, steht wobei Alkyl, CycloAlkyl, Alkenyl und Alkynyl Reste unsubstituiert sind oder gegebenenfalls ein- bis fünffach mit einem Rest aus der folgender Gruppe substituiert sind: Halogen, -N3, CN, NO2, OH, SH, CrC4Alkoxy, CpC4HaIOaIkOXy, C2-C4Alkenyloxy, C2-C4Haloalkenyloxy, C3-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 -
CAlkynyloxy, C3-C4Haloalkynyloxy, C3-C6CyClOaIlCyI-Ci-C4AIkOXy, C1-C4Ha- lkylcarbonyl, Ci-QHaloalkylcarbonyl, Ci-C4Alkoxycarbonyl, Ci-C4Alkylcarbonyl-Cr C4Alkyl, CrC4Alkoxycarbonyl-CrC4Alkyl, CrC4Alkylthio, C2-C4Alkylthio, C3- C4Alkynylthio, C3-C4Cycloalkyl- CrC4Alkylthio, C3-C4Haloalkynyl, C2-C4HaIo- alkenylthio, CrC4Haloalkylthio, CrC4Alkoxy-Ci-C4Alkyl, CrC4Haloalkoxy-Ci-C4Alkyl,CAlkynyloxy, C 3 -C 4 Haloalkynyloxy, C 3 -C 6 CyClOaIlCyI-Ci-C 4 -alkoxy, C 1 -C 4 lkylcarbonyl Ha-, Ci-QHaloalkylcarbonyl, Ci-C 4 alkoxycarbonyl, Ci-C 4 alkylcarbonyl-C 4 Cr alkyl, C r C 4 alkoxycarbonyl-C r C 4 alkyl, C r C 4 alkylthio, C 2 -C 4 alkylthio, C 3 - C 4 alkynylthio, C 3 -C 4 cycloalkyl, C r C 4 alkylthio, C 3 - C 4 haloalkynyl, C 2 -C 4 alkenylthio halo-, C r C 4 haloalkylthio, C r C 4 alkoxy-Ci-C 4 alkyl, C r C 4 haloalkoxy-Ci-C 4 alkyl,
C2-C4Alkenyloxy-CrC4Alkyl, C2-C4Haloalkenyloxy-CrC4Alkyl, C3-C4 Alkynyloxy-Cr C4Alkyl, NH2, NHC∑-CφAlkenyl, C2-C4Haloalkenyl, C3-C6AIkVnVl, C3-C6Cycloalkyl, C3- C6Cycloalkyl-CrC4Alkyl, C,-CaAlkoxy, C,-C4Haloalkoxy, C2-C4AIkBHyIoXy, C2- C4Haloalkenyloxy, C3-C4Alkynyloxy, C3-C4Haloalkynyloxy, C3-C6Cycloalkyl-Cr C4Alkoxy, CrC4Alkylcarbonyl, CrC4Haloalkyl- Carbonyl, CrC4Alkoxycarbonyl, Cr C 2 -C 4 alkenyloxyC r C 4 alkyl, C 2 -C 4 haloalkenyloxyC r C 4 alkyl, C 3 -C 4 alkynyloxyC r C 4 alkyl, NH 2 , NHC Σ -Cφ alkenyl, C 2 - C 4 haloalkenyl, C 3 -C 6 AIkVnVl, C 3 -C 6 cycloalkyl, C 3 - C 6 cycloalkyl-C r C 4 alkyl, C, -C a alkoxy, C, -C 4 haloalkoxy, C 2 -C 4 AIkBhyIoXy, C 2 -C 4 haloalkenyloxy, C 3 -C 4 alkynyloxy, C 3 -C 4 haloalkynyloxy, C 3 -C 6 cycloalkyl-Cr C 4 alkoxy, C r C 4 alkylcarbonyl, C r C 4 haloalkylcarbonyl, C r C 4 alkoxycarbonyl, C r
C4Alkylcarbonyl-Ci-C4Alkyl, Ci-C4Alkoxycarbonyl- CrC4Alkyl, CrC4Alkylthio, C2- C4Alkenylthio, QrQAlkynylthio, C3-C6Cycloalkyl-C) -C4AHCyUhIo, C3-C4HaIOaIk)TIyI, C2- QHaloalkenylthio, CrC4Haloalkylthio, Ci-C4AIkOXy-Ci-C6AIlCyI, Ci-C4Haloalkoxy-Cr C4Alkyl, CrGtAlkenyloxy-CrGtAlkyl, C2-C4Haloalkenyloxy-CrC4Alkyl, C3-C4Al- kynyloxy-Ci -C4AIlCyI, N(Ci-C4Alkyl)2, wobei die zwei Alkylgruppen jeweils unabhängig voneinander Ci-QAlkylcarbonylamino, Ci-GtHaloalkylcarbonylamino, Ci-C4-Alkoxy- carbonylamino und Ci-QAlkylarninocarbonylamino sein können.C 4 alkylcarbonyl-Ci-C4-alkyl, Ci-C 4 alkoxycarbonyl C r C 4 alkyl, C r C 4 alkylthio, C 2 - C 4 alkenylthio, QrQAlkynylthio, C 3 -C 6 cycloalkyl C) -C 4 AHCyUhIo , C 3 -C 4 HaIOaIk) Tiyi, C 2 - QHaloalkenylthio, C r C 4 haloalkylthio, Ci-C 4 -alkoxy-Ci-C 6 AIlCyI, Ci-C4-haloalkoxy-C r C 4 alkyl, CRG t alkenyloxy CRG t is alkyl, C 2 -C 4 haloalkenyloxyC r C 4 alkyl, C 3 -C 4 alkynyloxy-Ci-C 4 AlCliI, N (C 1 -C 4 alkyl) 2 , where the two alkyl groups are each independently of one another QAlkylcarbonylamino, Ci-G t Haloalkylcarbonylamino, Ci-C 4 alkoxycarbonylamino and Ci-QAlkylarninocarbonylamino can be.
W steht bevorzugt für "C(R32R33) und *C(R32R33)C(R34R35), wobei der Stern „*"W preferably stands for "C (R 32 R 33 ) and * C (R 32 R 33 ) C (R 34 R 35 ), where the star" * "
die Anbindung an O bedeutet und worin R32 bis R35 unabhängig und jeweils für Halogen, C,-C3Alkyl, C,-C3Alkoxy(Ci-C3)Alkyl oder Halo(C,-C3)Alkyl stehen,the bond to O and in which 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 steht besonders bevorzugt für C(R32R33), wobei R32R33 für Halogen oder Ci-CφAlkyl steht.W is particularly preferably C (R 32 R 33 ), where R 32 R 33 is halogen or Ci-CφAlkyl.
W steht ganz besonders bevorzugt für C(R32R33), wobei R32R33 für Halogen oder Methyl steht. n nimmt bevorzugt Werte von 0 bis 2 an.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 steht besonders bevorzugt für 0.n is particularly preferably 0.
R8 steht bevorzugt jeweils unabhängig voneinander für Wasserstoff, Halogen, HaIo(Q -C4)Al- kyl oder Nitro.R 8 is preferably in each case independently of one another hydrogen, halogen, Halo (Q -C 4 ) alkyl or nitro.
R8 steht besonders bevorzugt für Wasserstoff.R 8 particularly preferably represents hydrogen.
R10 und R11 stehen bevorzugt zusammengenommen für =0 oder für Wasserstoff.R 10 and R 11 taken together are preferably = 0 or hydrogen.
Die Verbindungen der Formel (I) können gegebenenfalls auch in Abhängigkeit von der Art der Substituenten als Stereoisomere, d.h. als geometrische und/oder als optische Isomere oder Isomerengemische in unterschiedlichen Zusammensetzungen vorliegen. Sowohl die reinen Stereo- isomeren als auch beliebige Gemische dieser Isomeren sind Gegenstand dieser Erfindung, auch wenn hier im Allgemeinen nur von den Verbindungen der Formel (I) die Rede ist.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.
Gegenstand der Erfindung sind auch die aus Verbindungen der Formel (I) durch Umsetzung mit basischen bzw. sauren Verbindungen gebildeten salzartigen Derivate.The invention also provides the salt-like derivatives formed from compounds of the formula (I) by reaction with basic or acidic compounds.
Bevorzugte Substituenten bzw. bevorzugte Bereiche der in den oben und nachstehend aufgeführten Formeln vorhandenen Reste werden im Folgenden definiert.Preferred substituents or preferred ranges of the radicals present in the formulas given above and below are defined below.
Die oben aufgeführten allgemeinen oder in Vorzugsbereichen aufgeführten Restedefinitionen gelten sowohl für die Endprodukte der Formel (I) als auch entsprechend für die jeweils zur Herstellung benötigten Ausgangs- oder Zwischenprodukte. Diese Restedefinitionen können untereinander, also auch zwischen den angegebenen bevorzugten Bereichen beliebig kombiniert werden.The general or preferred radical definitions given above apply both to the end products of the formula (I) and correspondingly to the starting materials or intermediates required in each case for the preparation. These remainder definitions can be combined with one another as desired, ie also between the specified preferred ranges.
Erfindungsgemäß bevorzugt werden die Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als bevorzugt aufgeführten Bedeutungen vorliegt.Preference according to the invention is given to the compounds of the formula (I) which contain a combination of the meanings listed above as being preferred.
Erfindungsgemäß besonders bevorzugt werden die Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als besonders bevorzugt aufgeführten Bedeutungen vorliegt.Particular preference according to the invention is given to the compounds of the formula (I) in which a combination of the meanings listed above as being particularly preferred is present.
Erfindungsgemäß ganz besonders bevorzugt werden die Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als ganz besonders bevorzugt aufgeführten Bedeutungen vorliegt. Erfindungsgemäß am meisten bevorzugt werden die Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als am meisten bevorzugt aufgeführten Bedeutungen vorliegt.Very particular preference according to the invention is given to the compounds of the formula (I) which contain a combination of the meanings given above as being very particularly preferred. Most preferred according to the invention are the compounds of the formula (I) in which a combination of the meanings listed above as being most preferred is present.
In den oben und nachstehend aufgeführten Restedefinitionen sind Kohlenwasserstoffreste, wie Alkyl - auch in Verbindung mit Heteroatomen wie in Alkoxy - soweit möglich jeweils geradkettig oder verzweigt.In the radical definitions given above and below, 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.
Die neuen substituierten Aryloxime der allgemeinen Formel (I) weisen interessante biologische Eigenschaften auf. Sie zeichnen sich insbesondere durch starke arthropodizide (insektizide und akarizide) sowie nematizide Wirksamkeit aus und können in der Landwirtschaft, in den Forsten, im Vorrats- und Materialschutz sowie im Hygienebereich verwendet werden.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.
Die neuen substituierten Aryloxime der allgemeinen Formel (I) sind gemäß folgendem allgemeinem Reaktionsschema darstellbar. Die Synthese der Ausgangsverbindungen der Formel (II) ist in DE 103 20 782 Al beschrieben.The 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 = Abgangsgruppe wie z. B. Cl oder Methansulfonyloxy (MeSθ2θ-) Die Vorstufen der allgemeinen Formel H2N-O-A2-X-R6 sind über folgenden Reaktionsweg zugänglich.LG = leaving group such. Cl or methanesulfonyloxy (MeSθ 2 θ-) The precursors of the general formula H 2 NOA 2 -XR 6 are accessible via the following reaction route.
MR = Mitsunobu-Reaktion; vergl. O.MR = Mitsunobu reaction; compare O.
Mitsunobu Synthesis (1981), S. 1-2Mitsunobu Synthesis (1981), p. 1-2
Für den Fall, dass die Brücke A 2 = _In the event that the bridge A 2 = _
ist, stellt sich das allgemeine Reaktionsschema für die Synthese von Verbindungen der allgemeinen Formel (I) wie folgt daris the general reaction scheme for the synthesis of compounds of general formula (I) is as follows
LG = Abgangsgruppe wie z. B. Cl oder Methansulfonyloxy (MeSO2O-) Für den Fall, dass die Brücke A 2 = _LG = leaving group such. Cl or methanesulfonyloxy (MeSO 2 O-) In the event that the bridge A 2 = _
ist, stellt sich das allgemeine Reaktionsschema für die Synthese von Verbindungen der allgemeinen Formel (I) wie folgt daris the general reaction scheme for the synthesis of compounds of general formula (I) is as follows
Entschützendeprotection
PG = Schutzgruppe wie z. B. Boc oder FmocPG = protecting group such. Boc or Fmoc
Gegebenenfalls können die Substituenten der Verbindungen der Formel, wie beispielsweise der Substituent R1 auch in weiteren Reaktionsschritten modifiziert werden. Beispielsweise kann in dem Fall, dass R1 für Halogen, insbesondere Fluor steht, in Gegenwart von nachstehend noch genannten basischen Reaktionshilfsmitteln ein nucleophiler Austausch mit geeigneten Nucleo- philen im Rahmen der Substituentendefinition von R1 vorgenommen werden Die Ausgangsstoffe der allgemeinen Formel (D) sind bekannt und/oder können nach an sich bekannten Verfahren hergestellt werden (vgl. Herstellungsbeispiele).Optionally, the substituents of the compounds of formula such as substituent R 1 may also be modified in further reaction steps. For example, in the case where 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).
Die Reaktionstemperaturen können bei der Durchführung des erfindungsgemäßen Verfahrens in einem größeren Bereich variiert werden. Im Allgemeinen arbeitet man bei Temperaturen zwischen 00C und 1500C, vorzugsweise zwischen 1O0C und 1200C.The 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.
Das erfindungsgemäße Verfahren wird im Allgemeinen unter Normaldruck durchgeführt. Es ist jedoch auch möglich, das erfindungsgemäße Verfahren unter erhöhtem oder vermindertem Druck - im allgemeinen zwischen 0,1 bar und 10 bar - durchzuführen.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.
Zur Durchführung des erfindungsgemäßen Verfahrens werden die Ausgangsstoffe im Allgemeinen in angenähert äquimolaren Mengen eingesetzt. Es ist jedoch auch möglich, eine der Komponenten in einem größeren Überschuss zu verwenden. Die Umsetzung wird im Allgemeinen in einem geeigneten Verdünnungsmittel in Gegenwart eines Reaktionshilfsmittels durchgeführt und das Reaktionsgemisch wird im Allgemeinen mehrere Stunden bei der erforderlichen Temperatur gerührt. Die Aufarbeitung wird nach üblichen Methoden durchgeführt (vgl. die Herstellungsbeispiele).To carry out the process according to the invention, 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).
Die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) können nach prinzipiell bekannten Methoden in andere Verbindungen der allgemeinen Formel (I) umgewandelt werden. Einige dieser möglichen Umwandlungsreaktionen sind im Folgenden beispielhaft skizziert: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:
Die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) können Salze bilden. Als geeignete Salze der Verbindungen der allgemeinen Formel (I) können übliche nicht toxische Salze, d.h. Salze mit Basen und Salze („Addukte") mit Säuren, genannt werden. Vorzugsweise sind Salze mit anorganischen Basen, wie Alkalimetallsalze, beispielsweise Natrium-, Kalium- oder Cäsiumsalze, Erdalkalimetallsalze, beispielsweise Calzium- oder Magnesiumsalze, Ammoniumsalze, Salze mit organischen Basen, insbesondere mit organischen Aminen, beispielsweise Triethylammonium-, Dicyclohexylammonium-, N,N'-Dibenzylethylendiammonium-, Pyridinium-, Picolinium- oder Ethanolammoniumsalze, Salze mit anorganischen Säuren, beispielsweise Hydrochloride, Hydrobromide, Dihydrosulfate, Trihydrosulfate, oder Phosphate, Salze mit organischen Carbonsäuren oder organischen Sulfosäuren, beispielsweise Formiate, Acetate, Trifluoracetate, Maleate, Tartrate, Methansulfonate, Benzolsulfonate oder para-Toluolsulfonate zu nennen.The compounds of the general formula (I) according to the invention can form salts. As suitable salts of the compounds of general formula (I), conventional non-toxic salts, i. 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, maleates, tartrates, methanesulfonates, benzenesulfonates or para-toluenesulfonates to name.
Salze werden gemäß den Standardverfahren zur Salzherstellung gebildet. Beispielsweise werden die erfindungsgemässen Verbindungen mit entsprechenden Säuren umgesetzt, um Säureadditionssalze zu bilden. Repräsentative Säureadditionssalze sind Salze, die sich beispielsweise durch die Reaktion mit anorganischen Säuren, wie beispielsweise Schwefelsäure, Salzsäure, Bromwasserstoffsäure, Phosphorsäure oder organischen Carbonsäuren wie Essigsäure, Trifluoressigsäure, Zitronensäure, Bernsteinsäure, Milchsäure, Ameisensäure, Maleinsäure, Camphersäure, Phthalsäure, Glycolsäure, Glutarsäure, Stearinsäure, Salicylsäure, Sorbinsäure, Zimtsäure, Pikrinsäure, Benzoesäure oder organischen Sulfonsäuren wie Methansulfonsäure und para-Toluolsulfonsäure bilden.Salts are formed according to standard salt preparation procedures. For example, 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.
Die Verbindungen der Formel (I) können gegebenenfalls in verschiedenen polymorphen Formen oder als Mischung verschiedener polymorpher Formen vorliegen. Sowohl die reinen Polymorphe als auch die Polymorphgemische sind Gegenstand der Erfindung und können erfindungsgemäß verwendet werden.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.
Die erfindungsgemäßen Wirkstoffe eignen sich bei guter Pflanzenverträglichkeit, günstiger Warm- blütertoxizität und guter Umweltverträglichkeit zum Schutz von Pflanzen und Pflanzenorganen, zur Steigerung der Ernteerträge, Verbesserung der Qualität des Erntegutes und zur Bekämpfung von tierischen Schädlingen, insbesondere Insekten, Spinnentieren, Helminthen, Nematoden und Mollusken, die in der Landwirtschaft, im Gartenbau, bei der Tierzucht, in Forsten, in Gärten und Freizeiteinrichtungen, im Vorrats- und Materialschutz sowie auf dem Hygienesektor vorkommen. Sie können vorzugsweise als Pflanzenschutzmittel eingesetzt werden. Sie sind gegen normal sensible und resistente Arten sowie gegen alle oder einzelne Entwicklungsstadien wirksam. Zu den oben erwähnten Schädlingen gehören: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:
Aus der Ordnung der Anoplura (Phthiraptera) z.B. Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Trichodectes spp.From the order of the Anoplura (Phthiraptera) e.g. Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Trichodectes spp.
Aus der Klasse der Arachnida z.B. 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.From the class of 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.
Aus der Klasse der Bivalva z.B. Dreissena spp.From the class of bivalva, e.g. Dreissena spp.
Aus der Ordnung der Chilopoda z.B. Geophilus spp., Scutigera spp. Aus der Ordnung der Coleoptera z.B. Acanthoscelides obtectus, Adoretus spp., Agelastica alni, Agriotes spp., Amphimallon solstitialis, Anobium punctatum, Anoplophora spp., Anthonomus spp., Anthrenus spp., Apogonia spp., Atomaria spp., Attagenus spp., Bruchidius obtectus, Bruchus spp., Ceuthorhynchus spp., Cleonus mendicus, Conoderus spp., Cosmopolites spp., Costelytra zea- landica, Curculio spp., Cryptorhynchus lapathi, Dermestes spp., Diabrotica spp., Epilachna spp., Faustinus cubae, Gibbium psylloides, Heteronychus arator, Hylamoφha elegans, Hylotrupes bajulus, Hypera postica, Hypothenemus spp., Lachnosterna consanguinea, Leptinotarsa decemlineata, Lissorhoptrus oryzophilus, Lixus spp., Lyctus spp., Meligethes aeneus, Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Otiorrhynchus sulcatus, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Popillia japonica, Premnotrypes spp., Psylliodes chryso- cephala, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Sitophilus spp., Sphenophorus spp., Stemechus spp., Symphyletes spp., Tenebrio molitor, Tribolium spp., Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp.From the order of Chilopoda eg Geophilus spp., Scutigera spp. From the order Coleoptera eg Acanthoscelides obtectus, Adoretus spp., Agelastica alni, Agriotes spp., Amphimallon solstitialis, Anobium punctatum, Anoplophora spp., Anthonomus spp., Anthrenus spp., Apogonia spp., Atomaria spp., Attagenus spp. Bruchidius obtectus, Bruchus spp., Ceuthorhynchus spp., Cleonus mendicus, Conoderus spp., Cosmopolites spp., Costelytra zealandica, Curculio spp., Cryptorhynchus lapathi, Dermestes spp., Diabrotica spp., Epilachna spp., Faustinus cubae, Gibbium psylloides, Heteronychus arator, Hylamoφha elegans, Hylotrupes bajulus, Hypera postica, Hypothenemus spp., Lachnosterna consanguinea, Leptinotarsa decemlineata, Lissorhoptrus oryzophilus, Lixus spp., Lyctus spp., Meligethes aeneus, Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Otiorrhynchus sulcatus, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Popillia japonica, Premnotrypes spp., Psyl liodes chrysoccephala, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Sitophilus spp., Sphenophorus spp., Stemechus spp., Symphyletes spp., Tenebrio molitor, Tribolium spp., Trogoderma spp., Tychius spp., Xylotrechus spp. Zabrus spp.
Aus der Ordnung der Collembola z.B. Onychiurus armatus.From the order of Collembola e.g. Onychiurus armatus.
Aus der Ordnung der Dermaptera z.B. Forficula auricularia.From the order of the Dermaptera e.g. Forficula auricularia.
Aus der Ordnung der Diplopoda z.B. Blaniulus guttulatus.From the order of diplopoda e.g. Blaniulus guttulatus.
Aus der Ordnung der Diptera z.B. Aedes spp., Anopheles spp., Bibio hortulanus, Calliphora erythrocephala, Ceratitis capitata, Chrysomyia spp., Cochliomyia spp., Cordylobia anthropophaga, Culex spp., Cuterebra spp., Dacus oleae, Dermatobia hominis, Drosophila spp., Fannia spp., Gastrophilus spp., Hylemyia spp., Hyppobosca spp., Hypoderma spp., Liriomyza spp.. Lucilia spp., Musca spp., Nezara spp., Oestrus spp., Oscinella frit, Pegomyia hyoscyami, Phorbia spp., Stomoxys spp., Tabanus spp., Tannia spp., Tipula paludosa, Wohlfahrtia spp.From the order of Diptera e.g. Aedes spp., Anopheles spp., Bibio hortulanus, Calliphora erythrocephala, Ceratitis capitata, Chrysomyia spp., Cochliomyia spp., Cordylobia anthropophaga, Culex spp., Cuterebra spp., Dacus oleae, Dermatobia hominis, Drosophila spp., Fannia spp. Gastrophilus spp., Hylemyia spp., Hyppobosca spp., Hypoderma spp., Liriomyza spp. Lucilia spp., Musca spp., Nezara spp., Oestrus spp., Oscinella frit, Pegomyia hyoscyami, Phorbia spp., Stomoxys spp. Tabanus spp., Tannia spp., Tipula paludosa, Wohlfahrtia spp.
Aus der Klasse der Gastropoda z.B. Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Succinea spp.From the class Gastropoda, e.g. Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Succinea spp.
Aus der Klasse der Helminthen z.B. 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., Loa Loa, Nematodirus spp., Oesophagostomum spp., Opisthorchis spp., Onchocerca volvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp, Strongyloides fuelleborni, Strongyloides stercoralis, Stronyloides spp., Taenia saginata, Taenia solium, Trichinella spiralis, Trichinella nativa, Trichinella britovi, Trichinella nelsoni, Trichinella pseudopsiralis, Trichostrongulus spp., Trichuris trichuria, Wuchereria bancrofti.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., Loa Loa, Nematodirus spp., Oesophagostomum spp., Opisthorchis spp., Onchocerca volvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp, Strongyloides fuelleborni, Strongyloides stercoralis, Stronyloides spp., Taenia saginata, Taenia solium, Trichinella spiralis, Trichinella nativa, Trichinella britovi, Trichinella nelsoni, Trichinella pseudopsiralis, Trichostrongulus spp., Trichuris trichuria, Wuchereria bancrofti.
Weiterhin lassen sich Protozoen, wie Eimeria, bekämpfen.Furthermore, protozoa, such as Eimeria, can be combated.
Aus der Ordnung der Heteroptera z.B. Anasa tristis, Antestiopsis spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., Eurygaster spp., 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.From the order of Heteroptera, e.g. Anasa tristis, Antestiopsis spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., Eurygaster spp. 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.
Aus der Ordnung der Homoptera z.B. Acyrthosipon spp., Aeneolamia spp., Agonoscena spp., Aleurodes spp., Aleurolobus barodensis, Aleurothrixus spp., Amrasca spp., Anuraphis cardui, Aonidiella spp., Aphanostigma piri, Aphis spp., Arboridia apicalis, Aspidiella spp., Aspidiotus spp., Atanus spp., Aulacorthum solani, Bemisia spp., Brachycaudus helichrysii, Brachycolus spp., Brevicoryne brassicae, Calligypona marginata, Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chromaphis juglandicola, Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp., Cryptomyzus ribis, Dalbulus spp., Dialeurodes spp., Diaphorina spp., Diaspis spp., Doralis spp., Drosicha spp., Dysaphis spp., Dysmicoccus spp., Empoasca spp., Eriosoma spp., Erythroneura spp., Euscelis bilobatus, Geococcus coffeae, Homalodisca coagulata, Hyalopterus arundinis, Icerya spp., Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., Lepidosaphes spp., Lipaphis erysimi, Macrosiphum spp., Mahanarva fimbriolata, Melanaphis sacchari, Metcalfiella spp., Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., Nasonovia ribisnigri, Nephotettix spp., Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Parabemisia myricae, Paratrioza spp., Parlatoria spp., Pemphigus spp., Pere- grinus maidis, Phenacoccus spp., Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., Pinnaspis aspidistrae, Planococcus spp., Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Psylla spp., Pteromalus spp., Pyrilla spp., Quadraspidiotus spp., Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., Saissetia spp., Scaphoides titanus, Schizaphis graminum, Selenaspidus articulatus, Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephala festina, Tenalaphara malayensis, Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., Tri- aleurodes vaporariorum, Trioza spp., Typhlocyba spp., Unaspis spp., Viteus vitifolii. _ -From the order of Homoptera eg Acyrthosipon spp., Aeneolamia spp., Agonoscena spp., Aleurodes spp., Aleurolobus barodensis, Aleurothrixus spp., Amrasca spp., Anuraphis cardui, Aonidiella spp., Aphanostigma piri, Aphis spp., Arboridia apicalis, Aspidiella spp., Aspidiotus spp., Atanus spp., Aulacorthum solani, Bemisia spp., Brachycaudus helichrysii, Brachycolus spp., Brevicoryne brassicae, Calligypona marginata, Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii, Chionetis tegalensis, Chlorita onukii, Chromaphis juglandicola, Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp., Cryptomyzus ribis, Dalbulus spp., Dialeurodes spp., Diaphorina spp., Diaspis spp., Doralis spp., Drosicha spp., Dysaphis spp. Dysmicoccus spp., Empoasca spp., Eriosoma spp., Erythroneura spp., Euscelis bilobatus, Geococcus coffeae, Homalodisca coagulata, Hyalopterus arundinis, Icerya spp., Idiocerus spp., Idioscopus spp., Laodelphax striatel lucid, Lecanium spp., Lepidosaphes spp., Lipaphis erysimi, Macrosiphum spp., Mahanarva fimbriolata, Melanaphis sacchari, Metcalfiella spp., Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., Nasonovia ribisnigri, Nephotettix spp., Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Parabemisia myricae, Paratrioza spp., Parlatoria spp., Pemphigus spp., Peregrinus maidis, Phenacoccus spp., Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., Pinnaspis aspidistrae, Planococcus spp., Protopulvinaria pyriformis , Pseudaulacaspis pentagona, Pseudococcus spp., Psylla spp., Pteromalus spp., Pyrilla spp., Quadraspidiotus spp., Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., Saissetia spp., Scaphoides titanus, Schizaphis graminum, Selenaspidus articulatus, Sogata spp Sogatella furcifera, Sogatodes spp., Stictocephala festina, Tenalaphara malayensis, Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., Trialurodes vaporariorum, Trioza spp., Typhlo cyba spp., Unaspis spp., Viteus vitifolii. _ -
Aus der Ordnung der Hymenoptera z.B. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.From the order of Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
Aus der Ordnung der Isopoda z.B. Armadillidium vulgäre, Oniscus asellus, Porcellio scaber.From the order of isopods e.g. Armadillidium vulgaris, Oniscus asellus, Porcellio scaber.
Aus der Ordnung der Isoptera z.B. Reticulitermes spp., Odontotermes spp.From the order of Isoptera e.g. Reticulitermes spp., Odontotermes spp.
Aus der Ordnung der Lepidoptera z.B. Acronicta major, Aedia leucomelas, Agrotis spp., Alabama argillacea, Anticarsia spp., Barathra brassicae, Bucculatrix thurberiella, Bupalus piniarius, Cacoecia podana, Capua reticulana, Caφocapsa pomonella, Cheimatobia brumata, Chilo spp., Choristoneura fumiferana, Clysia ambiguella, Cnaphalocerus spp., Earias insulana, Ephestia kuehniella, Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleria mellonella, Helicoveφa spp., Heliothis spp., Hofmannophila pseudospretella, Homona magnanima, Hyponomeuta padella, La- phygma spp., Lithocolletis blancardella, Lithophane antennata, Loxagrotis albicosta, Lymantria spp., Malacosoma neustria, Mamestra brassicae, Mocis repanda, Mythimna separata, Oria spp., Oulema oryzae, Panolis flammea, Pectinophora gossypiella, Phyllocnistis citrella, Pieris spp., Plutella xylostella, Prodenia spp., Pseudaletia spp., Pseudoplusia includens, Pyrausta nubilalis, Spodoptera spp., Thermesia gemmatalis, Tinea pellionella, Tineola bisselliella, Tortrix viridana, Trichoplusia spp.From the order of Lepidoptera e.g. Acronicta major, Aedia leucomelas, Agrotis spp., Alabama argillacea, Anticarsia spp., Barathra brassicae, Bucculatrix thurberiella, Bupalus pinarius, Cacoecia podana, Capua reticulana, Caφocapsa pomonella, Cheimatobia brumata, Chilo spp., Choristoneura fumiferana, Clysia ambiguella, Cnaphalocerus spp , Earias insulana, Ephestia kuehniella, Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleria mellonella, Helicovepha spp., Heliothis spp., Hofmannophila pseudospretella, Homona magnanima, Hyponomeuta padella, Lophygma spp., Lithocolletis blancardella, Lithophane antennata , Loxagrotis albicosta, Lymantria spp., Malacosoma neustria, Mamestra brassicae, Mocis repanda, Mythimna separata, Oria spp., Oulema oryzae, Panolis flammea, Pectinophora gossypiella, Phyllocnistis citrella, Pieris spp., Plutella xylostella, Prodenia spp., Pseudaletia spp. , Pseudoplusia includens, Pyrausta nubilalis, Spodoptera spp., Thermesia gemmatalis, Tinea pellionella, Tineola bisselliella, Tortrix viridana, Trichoplusia spp.
Aus der Ordnung der Orthoptera z.B. Acheta domesticus, Blatta orientalis, Blattella germanica, Gryllotalpa spp., Leucophaea maderae, Locusta spp., Melanoplus spp., Periplaneta americana, Schistocerca gregaria.From the order of Orthoptera e.g. Acheta domesticus, Blatta orientalis, Blattella germanica, Gryllotalpa spp., Leucophaea maderae, Locusta spp., Melanoplus spp., Periplaneta americana, Schistocerca gregaria.
Aus der Ordnung der Siphonaptera z.B. Ceratophyllus spp., Xenopsylla cheopis.From the order of siphonaptera e.g. Ceratophyllus spp., Xenopsylla cheopis.
Aus der Ordnung der Symphyla z.B. Scutigerella immaculata.From the order of Symphyla e.g. Scutigerella immaculata.
Aus der Ordnung der Thysanoptera z.B. Baliothrips biformis, Enneothrips flavens, Frankliniella spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamoni, Thrips spp.From the order of Thysanoptera e.g. Baliothrips biformis, Enneothrips flavens, Frankliniella spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamoni, Thrips spp.
Aus der Ordnung der Thysanura z.B. Lepisma saccharina.From the order of Thysanura e.g. Lepisma saccharina.
Zu den pflanzenparasitären Nematoden gehören z.B. 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. Die erfindungsgemäßen Verbindungen der Formel (I) zeichnen sich insbesondere durch starke Wirkung gegen...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 ...
Die erfindungsgemäßen Verbindungen können gegebenenfalls in bestimmten Konzentrationen bzw. Aufwandmengen auch als Herbizide, Safener, Wachstumsregulatoren oder Mittel zur Verbesserung der Pflanzeneigenschaften, oder als Mikrobizide, beispielsweise als Fungizide, Antimykotika, Bakterizide, Virizide (einschließlich Mittel gegen Viroide) oder als Mittel gegen MLO (Mycoplasma-like-organism) und RLO (Rickettsia-like-organism) verwendet werden. Sie lassen sich gegebenenfalls auch als Zwischen- oder Vorprodukte für die Synthese weiterer Wirkstoffe einsetzen.If appropriate, 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.
Erfindungsgemäß können alle Pflanzen und Pflanzenteile behandelt werden. Unter Pflanzen werden hierbei alle Pflanzen und Pflanzenpopulationen verstanden, wie erwünschte und unerwünschte Wildpflanzen oder Kulturpflanzen (einschließlich natürlich vorkommender Kulturpflanzen). Kulturpflanzen können Pflanzen sein, die durch konventionelle Züchtungs- und Optimierungsmethoden oder durch biotechnologische und gentechnologische Methoden oder Kombi- nationen dieser Methoden erhalten werden können, einschließlich der transgenen Pflanzen und einschließlich der durch Sortenschutzrechte schützbaren oder nicht schützbaren Pflanzensorten. Unter Pflanzenteilen sollen alle oberirdischen und unterirdischen Teile und Organe der Pflanzen, wie Sproß, Blatt, Blüte und Wurzel verstanden werden, wobei beispielhaft Blätter, Nadeln, Stengel, Stämme, Blüten, Fruchtkörper, Früchte und Saatgut sowie Wurzeln, Knollen und Rhizome aufgeführt werden. Zu den Pflanzenteilen gehört auch Erntegut sowie vegetatives und generatives Vermehrungsmaterial, beispielsweise Stecklinge, Knollen, Rhizome, Ableger und Saatgut.According to the invention, all plants and parts of plants can be treated. In this context, 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.
Die erfindungsgemäße Behandlung der Pflanzen und Pflanzenteile mit den Wirkstoffen erfolgt direkt oder durch Einwirkung auf deren Umgebung, Lebensraum oder Lagerraum nach den üblichen Behandlungsmethoden, z.B. durch Tauchen, Sprühen, Verdampfen, Vernebeln, Streuen, Aufstreichen, Injizieren und bei Vermehrungsmaterial, insbesondere bei Saatgut, weiterhin durch ein- oder mehrschichtiges Umhüllen.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.
Die Wirkstoffe können in die üblichen Formulierungen überfuhrt werden, wie Lösungen, Emulsionen, Spritzpulver, wasser- und ölbasierte Suspensionen, Pulver, Stäubemittel, Pasten, lös- liehe Pulver, lösliche Granulate, Streugranulate, Suspensions-Emulsions-Konzentrate, Wirkstoff- imprägnierte Naturstoffe, Wirkstoff-imprägnierte synthetische Stoffe, Düngemittel sowie Feinst- verkapselungen in polymeren Stoffen. . .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. , ,
Diese Formulierungen werden in bekannter Weise hergestellt, z.B. durch Vermischen der Wirkstoffe mit Streckmitteln, also flüssigen Lösungsmitteln und/oder festen Trägerstoffen, gegebenenfalls unter Verwendung von oberflächenaktiven Mitteln, also Emulgiermitteln und/oder Dispergiermitteln und/oder schaumerzeugenden Mitteln. Die Herstellung der Formulierungen erfolgt entweder in geeigneten Anlagen oder auch vor oder während der Anwendung.These 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. The preparation of the formulations is carried out either in suitable systems or before or during use.
Als Hilfsstoffe können solche Stoffe Verwendung finden, die geeignet sind, dem Mittel selbst oder und/oder davon abgeleitete Zubereitungen (z.B. Spritzbrühen, Saatgutbeizen) besondere Eigenschaften zu verleihen, wie bestimmte technische Eigenschaften und/oder auch besondere biologische Eigenschaften. Als typische Hilfsmittel kommen in Frage: Streckmittel, Lösemittel und Trägerstoffe.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.
Als Streckmittel eignen sich z.B. Wasser, polare und unpolare organische chemische Flüssigkeiten z.B. aus den Klassen der aromatischen und nicht-aromatischen Kohlenwasserstoffe (wie Paraffine, Alkylbenzole, Alkylnaphthaline, Chlorbenzole), der Alkohole und Polyole (die ggf. auch substituiert, verethert und/oder verestert sein können), der Ketone (wie Aceton, Cyclohexanon), Ester (auch Fette und Öle) und (poly-)Ether, der einfachen und substituierten Amine, Amide, Lactame (wie N-Alkylpyrrolidone) und Lactone, der Sulfone und Sulfoxide (wie Dimethylsysulfoxid).As extender, e.g. Water, 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).
Im Falle der Benutzung von Wasser als Streckmittel können z.B. auch organische Lösemittel als Hilfslösungsmittel verwendet werden. Als flüssige Lösemittel kommen im wesentlichen in Frage: Aromaten, wie Xylol, Toluol, oder Alkylnaphthaline, chlorierte Aromaten und chlorierte aliphatische Kohlenwasserstoffe, wie Chlorbenzole, Chlorethylene oder Methylenchlorid, alipha- tische Kohlenwasserstoffe, wie Cyclohexan oder Paraffine, z.B. Erdölfraktionen, mineralische und pflanzliche Öle, Alkohole, wie Butanol oder Glykol sowie deren Ether und Ester, Ketone wie Aceton, Methylethylketon, Methylisobutylketon oder Cyclohexanon, stark polare Lösungsmittel, wie Dimethylsulfoxid, sowie Wasser.In the case of using water as an extender, e.g. also organic solvents can be used as auxiliary solvent. 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.
Als feste Trägerstoffe kommen in Frage:Suitable solid carriers are:
z.B. Ammoniumsalze und natürliche Gesteinsmehle, wie Kaoline, Tonerden, Talkum, Kreide, Quarz, Attapulgit, Montmorillonit oder Diatomeenerde und synthetische Gesteinsmehle, wie hochdisperse Kieselsäure, Aluminiumoxid und Silikate, als feste Trägerstoffe für Granulate kommen in Frage: z.B. gebrochene und fraktionierte natürliche Gesteine wie Calcit, Marmor, Bims, Sepiolith, Dolomit sowie synthetische Granulate aus anorganischen und organischen Mehlen sowie Granulate aus organischem Material wie Papier, Sägemehl, Kokosnußschalen, Maiskolben und Tabakstengeln; als Emulgier- und/oder schaumerzeugende Mittel kommen in Frage: z.B. nichtionogene und anionische Emulgatoren, wie Polyoxyethylen-Fettsäure-Ester, Polyoxyethylen- . _For example, 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 , _
Fettalkohol-Ether, z.B. Alkylaryl-polyglykolether, Alkylsulfonate, Alkylsulfate, Arylsulfonate sowie Einweißhydrolysate; als Dispergiermittel kommen in Frage nicht-ionische und/oder ionische Stoffe, z.B. aus den Klassen der Alkohol-POE- und/oder POP-Ether, Säure- und/oder POP- POE- Ester, Alkyl-Aryl- und/oder POP- POE-Ether, Fett- und/oder POP- POE-Addukte, POE- und/oder POP-Polyol Derivate, POE- und/oder POP-Sorbitan- oder-Zucker-Addukte, Alky- oder Aryl- Sulfate, Sulfonate und Phosphate oder die entsprechenden PO-Ether-Addukte. Ferner geeignete Oligo- oder Polymere, z.B. ausgehend von vinylischen Monomeren, von Acrylsäure, aus EO und/oder PO allein oder in Verbindung mit z.B. (poly-) Alkoholen oder (poly-) Aminen. Ferner können Einsatz finden Lignin und seine Sulfonsäure-Derivate, einfache und modifizierte Cellulosen, aromatische und/oder aliphatische Sulfonsäuren sowie deren Addukte mit Formaldehyd.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. from the classes of alcohol POE and / or POP ethers, acid and / or POP POE esters, alkyl aryl and / or POP POE ethers, fatty and / or POP POE adducts, POE and / or POP polyol derivatives, POE and / or POP sorbitol or sugar adducts, alkyl or aryl sulfates, sulfonates and phosphates or the corresponding PO ether adducts. Further suitable oligo- or polymers, e.g. starting from vinylic monomers, from acrylic acid, from EO and / or PO alone or in combination with e.g. (poly) alcohols or (poly) amines. Furthermore, find use lignin and its sulfonic acid derivatives, simple and modified celluloses, aromatic and / or aliphatic sulfonic acids and their adducts with formaldehyde.
Es können in den Formulierungen Haftmittel wie Carboxymethylcellulose, natürliche und synthetische pulvrige, körnige oder latexförmige Polymere verwendet werden, wie Gummi- arabicum, Polyvinylalkohol, Polyvinylacetat, sowie natürliche Phospholipide, wie Kephaline und Lecithine und synthetische Phospholipide.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.
Es können Farbstoffe wie anorganische Pigmente, z.B. Eisenoxid, Titanoxid, Ferrocyanblau und organische Farbstoffe, wie Alizarin-, Azo- und Metallphthalocyaninfarbstoffe und Spurennährstoffe wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink verwendet werden.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.
Weitere Additive können Duftstoffe, mineralische oder vegetabile gegebenenfalls modifizierte Öle, Wachse und Nährstoffe (auch Spurennährstoffe), wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink sein.Other 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.
Weiterhin enthalten sein können Stabilisatoren wie Kältestabilisatoren, Konservierungsmittel, Oxidationsschutzmittel, Lichtschutzmittel oder andere die chemische und / oder physikalische Stabilität verbessernde Mittel.Stabilizers such as cold stabilizers, preservatives, antioxidants, light stabilizers or other chemical and / or physical stability-improving agents may also be present.
Die Formulierungen enthalten im allgemeinen zwischen 0,01 und 98 Gew.-% Wirkstoff, vorzugsweise zwischen 0,5 und 90 %.The formulations generally contain between 0.01 and 98% by weight of active ingredient, preferably between 0.5 and 90%.
Der erfindungsgemäße Wirkstoff kann in seinen handelsüblichen Formulierungen sowie in den aus diesen Formulierungen bereiteten Anwendungsformen in Mischung mit anderen Wirkstoffen wie Insektiziden, Lockstoffen, Sterilantien, Bakteriziden, Akariziden, Nematiziden, Fungiziden, wachstumsregulierenden Stoffen, Herbiziden, Safenern, Düngemitteln oder Semiochemicals vorliegen. Besonders günstige Mischpartner sind z.B. die folgenden: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. Particularly favorable mixing partners are, for example, the following:
Fungizide:fungicides:
2-Phenylphenol; 8-Hydroxyqυinoline Sulfate; Acibenzolar-S-methyl; Aldimorph; Amidoflumet;2-phenylphenol; 8-hydroxyquinoline sulfates; Acibenzolar-S-methyl; aldimorph; amidoflumet;
Ampropylfos; Ampropylfos-potassium; Andoprim; Anilazine; Azaconazole; Azoxystrobin; Benalaxyl; Benodanil; Benomyl; Benthiavalicarb-isopropyl; Benzamacril; Benzamacril-isobutyl;Ampropylfos; Ampropylfos-potassium; andoprim; anilazine; azaconazole; azoxystrobin; benalaxyl; Benodanil; benomyl; Benthiavalicarb-isopropyl; Benzamacril; Benzamacril-isobutyl;
Bilanafos; Binapacryl; Biphenyl; Bitertanol; Blasticidin-S; Bromuconazole; Bupirimate;bilanafos; binapacryl; biphenyl; bitertanol; Blasticidin-S; bromuconazole; Bupirimate;
Buthiobate; Butylamine; Calcium polysulfide; Capsimycin; Captafol; Captan; Carbendazim;Buthiobate; butylamine; Calcium polysulfides; capsimycin; captafol; captan; carbendazim;
Carboxin; Caφropamid; Carvone; Chinomethionat; Chlobenthiazone; Chlorfenazole; Chloroneb;carboxin; Caφropamid; carvones; chinomethionat; Chlobenthiazone; Chlorfenazole; chloroneb;
Chlorothalonil; Chlozolinate; Clozylacon; Cyazofamid; Cyflufenamid; Cymoxanil; Cyprocon- azole; Cyprodinil; Cyprofuram; Dagger G; Debacarb; Dichlofluanid; Dichlone; Dichlorophen;chlorothalonil; chlozolinate; Clozylacon; cyazofamid; cyflufenamid; cymoxanil; Cyproconazoles; cyprodinil; cyprofuram; Dagger G; debacarb; dichlofluanid; dichlone; dichlorophen;
Diclocymet; Diclomezine; Dicloran; Diethofencarb; Difenoconazole; Diflumetorim; Dimethirimol;diclocymet; Diclomezine; dicloran; diethofencarb; Difenoconazole; diflumetorim; dimethirimol;
Dimethomoφh; Dimoxystrobin; Diniconazole; Diniconazole-M; Dinocap; Diphenylamine;Dimethomoφh; dimoxystrobin; diniconazole; Diniconazole-M; dinocap; diphenylamines;
Dipyrithione; Ditalimfos; Dithianon; Dodine; Drazoxolon; Edifenphos; Epoxiconazole;Dipyrithione; Ditalimfos; dithianon; dodine; Drazoxolon; edifenphos; epoxiconazole;
Ethaboxam; Ethirimol; Etridiazole; Famoxadone; Fenamidone; Fenapanil; Fenarimol; Fenbuconazole; Fenfuram; Fenhexamid; Fenitropan; Fenoxanil; Fenpiclonil; Fenpropidin;ethaboxam; ethirimol; etridiazole; famoxadone; fenamidone; Fenapanil; fenarimol; Fenbuconazole; fenfuram; fenhexamid; Fenitropan; fenoxanil; fenpiclonil; fenpropidin;
Fenpropimorph; Ferbam; Fluazinam; Flubenzimine; Fludioxonil; Flumetover; Flumoφh;fenpropimorph; ferbam; fluazinam; Flubenzimine; fludioxonil; flumetover; Flumoφh;
Fluoromide; Fluoxastrobin; Fluquinconazole; Flurprimidol; Flusilazole; Flusulfamide; Flutolanil;fluoromides; fluoxastrobin; fluquinconazole; flurprimidol; flusilazole; flusulfamide; flutolanil;
Flutriafol; Folpet; Fosetyl-Al; Fosetyl-sodium; Fuberidazole; Furalaxyl; Furametpyr; Furcarbanil;flutriafol; folpet; Fosetyl-Al; Fosetyl-sodium; fuberidazole; furalaxyl; furametpyr; Furcarbanil;
Furmecyclox; Guazatine; Hexachlorobenzene; Hexaconazole; Hymexazol; Imazalil; Imibenconazole; Iminoctadine triacetate; Iminoctadine tris(albesilate); Iodocarb; Ipconazole;Furmecyclox; guazatine; Hexachlorobenzene; hexaconazole; hymexazol; imazalil; Imibenconazole; Iminoctadine triacetate; Iminoctadine tris (albesilate); iodocarb; ipconazole;
Iprobenfos; Iprodione; Iprovalicarb; Irumamycin; Isoprothiolane; Isovaledione; Kasugamycin;iprobenfos; iprodione; iprovalicarb; Irumamycin; isoprothiolane; Isovaledione; kasugamycin;
Kresoxim-methyl; Mancozeb; Maneb; Meferimzone; Mepanipyrim; Mepronil; Metalaxyl;Kresoxim-methyl; mancozeb; maneb; Meferimzone; mepanipyrim; mepronil; metalaxyl;
Metalaxyl-M; Metconazole; Methasulfocarb; Methfuroxam; Metiram; Metominostrobin;Metalaxyl-M; metconazole; methasulfocarb; Methfuroxam; metiram; metominostrobin;
Metsulfovax; Mildiomycin; Myclobutanil; Myclozolin; Natamycin; Nicobifen; Nitrothal- isopropyl; Noviflumuron; Nuarimol; Ofurace; Orysastrobin; Oxadixyl; Oxolinic acid; Oxpocon- azole; Oxycarboxin; Oxyfenthiin; Paclobutrazol; Pefurazoate; Penconazole; Pencycuron;Metsulfovax; mildiomycin; myclobutanil; myclozoline; natamycin; nicobifen; Nitrothal isopropyl; Noviflumuron; nuarimol; ofurace; orysastrobin; oxadixyl; Oxolinic acid; Oxpoconazoles; oxycarboxin; Oxyfenthiin; paclobutrazol; Pefurazoate; penconazole; pencycuron;
Phosdiphen; Phthalide; Picoxystrobin; Piperalin; Polyoxins; Polyoxorim; Probenazole; Prochloraz;phosdiphen; phthalides; picoxystrobin; piperalin; Polyoxins; Polyoxorim; Probenazole; prochloraz;
Procymidone; Propamocarb; Propanosine-sodium; Propiconazole; Propineb; Proquinazid;procymidone; propamocarb; Propanosine-sodium; propiconazole; propineb; proquinazid;
Prothioconazole; Pyraclostrobin; Pyrazophos; Pyrifenox; Pyrimethanil; Pyroquilon; Pyroxyfur; Pyrrolnitrine; Quinconazole; Quinoxyfen; Quintozene; Simeconazole; Spiroxamine; Sulfur;prothioconazole; pyraclostrobin; Pyrazohos; pyrifenox; pyrimethanil; pyroquilon; Pyroxyfur; Pyrrolnitrine; Quinconazole; quinoxyfen; quintozene; Simeconazole; spiroxamine; Sulfur;
Tebuconazole; Tecloftalam; Tecnazene; Tetcyclacis; Tetraconazole; Thiabendazole; Thicyofen;tebuconazole; tecloftalam; Tecnazene; Tetcyclacis; tetraconazole; thiabendazole; Thicyofen;
Thifluzamide; Thiophanate-methyl; Thiram; Tioxymid; Tolclofos-methyl; Tolylfluanid; Tria- dimefon; Triadimenol; Triazbutil; Triazoxide; Tricyclamide; Tricyclazole; Tridemoφh;Thifluzamide; Thiophanate-methyl; thiram; Tioxymid; Tolclofos-methyl; tolylfluanid; Triadimefon; triadimenol; Triazbutil; triazoxide; Tricyclamide; Tricyclazole; Tridemoφh;
Trifloxystrobin; Triflumizole; Triforine; Triticonazole; Uniconazole; Validamycin A; Vinclozolin; Zineb; Ziram; Zoxamide; (2S)-N-[2-[4-[[3-(4-chloφhenyl)-2-propynyl]oxy]-3-methoxyphenyl]- ethyl]-3-methyl- 2-[(methylsulfonyl)amino]-butanamide; l-(l-naphthalenyl)-lH-pyrrole-2,5-dione; 2,3,5,6-tetrachlor-4-(methylsulfonyl)-pyridine; 2-amino-4-methyl-N-phenyl-5-thiazolecarboxarni- de; 2-chlor-N-(2,3-dihydro-l,l,3-trimethyl-lH-inden-4-yl)-3-pyridincarboxamide; 3,4,5-trichlor- 2,6-pyridinedicarbonitrile; Actinovate; cis-l-(4-chlorphenyl)-2-(lH-l,2,4-triazole-l-yl)-cyclohep- tanol; methyl l-(2,3-dihydro-2,2-dimethyl-lH-inden-l-yl)-lH-imidazole-5-carboxylate; mono- potassium carbonate; N-(6-methoxy-3-pyridinyl)-cyclopropanecarboxamide; N-butyl-8-(l,l-dime- thylethyl)-l-oxaspiro[4.5]decan-3-amine; Sodium tetrathiocarbonate; sowie Kupfersalze und -Zubereitungen, wie Bordeaux mixture; Copper hydroxide; Copper naphthenate; Copper oxychloride; Copper sulfate; Cufraneb; Cuprous oxide; Mancopper; Oxine-copper.trifloxystrobin; triflumizole; triforine; triticonazole; Uniconazole; Validamycin A; vinclozolin; Zineb; ziram; zoxamide; (2S) -N- [2- [4 - [[3- (4-chloφhenyl) -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; 3,4,5-trichloro-2,6-pyridinedicarbonitrile; Actinovate; cis-1- (4-chlorophenyl) -2- (1H-l, 2,4-triazole-1-yl) -cycloheptanol; methyl 1- (2,3-dihydro-2,2-dimethyl-1H-inden-1-yl) -1H-imidazole-5-carboxylates; monopotassium carbonate; N- (6-methoxy-3-pyridinyl) -cyclopropanecarboxamide; N-butyl-8- (1,1-dimethylethyl) -1-oxaspiro [4.5] decan-3-amine; Sodium tetrathiocarbonate; and copper salts and preparations, such as Bordeaux mixture; Copper hydroxide; Copper naphthenates; Copper oxychloride; Copper sulfate; Cufraneb; Cuprous oxides; mancopper; Oxine-copper.
Bakterizide:bactericides:
Bronopol, Dichlorophen, Nitrapyrin, Nickel-Dimethyldithiocarbamat, Kasugamycin, Octhilinon, Furancarbonsäure, Oxytetracyclin, Probenazol, Streptomycin, Tecloftalam, Kupfersulfat und andere Kupfer-Zubereitungen.Bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulfate and other copper preparations.
Insektizide / Akarizide / Nematizide:Insecticides / acaricides / nematicides:
Acetylcholinesterase (AChE) InhibitorenAcetylcholinesterase (AChE) inhibitors
1.1 Carbamate, zum Beispiel Alanycarb, Aldicarb, Aldoxycarb, Allyxycarb, Aminocarb, Bendiocarb, Ben- furacarb, Bufencarb, Butacarb, Butocarboxim, Butoxycarboxim, Carbaryl, Carbofuran, Carbosulfan, Cloethocarb, Dimetilan, Ethiofencarb, Fenobucarb, Fenothiocarb, Formetanate, Furathiocarb, Isoprocarb, Metam-sodium, Methiocarb, Methomyl,1.1 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,
Metolcarb, Oxamyl, Pirimicarb, Promecarb, Propoxur, Thiodicarb, Thiofanox, Trimethacarb, XMC, Xylylcarb, TriazamateMetolcarb, Oxamyl, Pirimicarb, Promecarb, Propoxur, Thiodicarb, Thiofanox, Trimethacarb, XMC, Xylylcarb, Triazamates
1.2 Organophosphate, zum Beispiel Acephate, Azamethiphos, Azinphos (-methyl, -ethyl), Bromophos-ethyl, Bromfenvinfos (-methyl), Butathiofos, Cadusafos, Carbophenothion, Chlorethoxyfos,1.2 Organophosphates, for example acephates, azamethiphos, azinphos (-methyl, -ethyl), bromophos-ethyl, bromfenvinfos (-methyl), butathiofos, cadusafos, carbophenothione, chloroethoxyfos,
Chlorfenvinphos, Chlormephos, Chloφyrifos (-methyl/-ethyl), Coumaphos, Cyanofen- phos, Cyanophos, Chlorfenvinphos, Demeton-S-methyl, Demeton-S-methylsulphon,Chlorfenvinphos, chlormephos, chloφyrifos (-methyl / -ethyl), coumaphos, cyanofephos, cyanophos, chlorfenvinphos, demeton-S-methyl, demeton-S-methylsulphone,
Dialifos, Diazinon, Dichlofenthion, Dichlorvos/DDVP, Dicrotophos, Dimethoate, Di- methylvinphos, Dioxabenzofos, Disulfoton, EPN, Ethion, Ethoprophos, Etrimfos, Famphur, Fenamiphos, Fenitrothion, Fensulfothion, Fenthion, Flupyrazofos, Fonofos,Dialifos, Diazinon, Dichlofenthione, Dichlorvos / DDVP, Dicrotophos, Dimethoate, Dimethylvinphos, Dioxabenzofos, Disulfoton, EPN, Ethion, Ethoprophos, Etrimfos, Famphur, Fenamiphos, Fenitrothion, Fensulfothion, Fenthion, Flupyrazofos, Fonofos,
Formothion, Fosmethilan, Fosthiazate, Heptenophos, Iodofenphos, Iprobenfos, Isazofos,Formothion, Fosmethilan, Fosthiazate, Heptenophos, Iodofenphos, Iprobenfos, Isazofos,
Isofenphos, Isopropyl O-salicylate, Isoxathion, 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, Pyrida- thion, Quinalphos, Sebufos, Sulfotep, Sulprofos, Tebupirimfos, Temephos, Terbufos,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,
Tetrachlorvinphos, Thiometon, Triazophos, Triclorfon, VamidothionTetrachlorvinphos, thiometone, triazophos, triclorfone, vamidothion
Natrium-Kanal-Modulatoren / Spannungsabhängige Natrium-Kanal-BlockerSodium Channel Modulators / Voltage-Dependent Sodium Channel Blockers
2.1 Pyrethroide, zum Beispiel Acrinathrin, Allethrin (d-cis-trans, d-trans), Beta-Cyfluthrin, Bifenthrin, Bioallethrin, Bioallethrin-S-cyclopentyl-isomer, Bioethanomethrin, Biopermethrin, Biores- methrin, Chlovaporthrin, Cis-Cypermetbxin, Cis-Resmethrin, Cis-Permethrin, Clocythrin, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cypermethrin (alpha-, beta-, theta-, zeta-), Cy- phenothrin, Deltamethrin, Empenthrin (lR-isomer), Esfenvalerate, Etofenprox, Fenfluthrin, Fenpropathrin, Fenpyrithrin, Fenvalerate, Flubrocythrinate, Flucythrinate, Flufenprox, Flumethrin, Fluvalinate, Fubfenprox, Gamma-Cyhalothrin, Imiprothrin,2.1 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, fenpyrithrin, fenvalerate, flubrocythrinates, flucythrinates, flufenprox, flumethrin, fluvalinate, fubfenprox, gamma-cyhalothrin, imiprothrin,
Kadethrin, Lambda-Cyhalothrin, Metofluthrin, Permethrin (eis-, trans-), Phenothrin (IR- trans isomer), Prallethrin, Profluthrin, Protrifenbute, Pyresmethrin, Resmethrin, RU 15525, Silafluofen, Tau-Fluvalinate, Tefluthrin, Terallethrin, Tetramethrin (-1R- isomer), Tralomethrin, Transfluthrin, ZXI 8901, Pyrethrins (pyrethrum)Kadethrin, lambda-cyhalothrin, metofluthrin, permethrin (cis, trans), phenothrin (IR trans isomer), prallethrin, profuthrin, protrifenbute, pyresmethrin, resmethrin, RU 15525, silafluofen, tau-fluvalinate, tefluthrin, terallethrin, tetramethrin ( -1R- isomer), tralomethrin, transfluthrin, ZXI 8901, pyrethrins (pyrethrum)
DDTDDT
2.2 Oxadiazine, zum Beispiel Indoxacarb2.2 Oxadiazines, for example indoxacarb
Acetylcholin-Rezeptor-Agonisten/-AntagonistenAcetylcholine receptor agonists / antagonists
3.1 Chlomicotinyle, zum Beispiel Acetamiprid, Clothianidin, Dinotefuran, Imidacloprid, Nitenpyram, Ni- thiazine, Thiacloprid, Thiamethoxam3.1 Chlomicotinyls, for example acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazines, thiacloprid, thiamethoxam
3.2 Nicotine, Bensultap, Cartap3.2 Nicotine, Bensultap, Cartap
Acetylcholin-Rezeptor-ModulatorenAcetylcholine receptor modulators
4.1 Spinosyne, zum Beispiel Spinosad _4.1 Spinosyns, for example spinosad _
GABA-gesteuerte Chlorid-Kanal-AntagonistenGABA-driven chloride channel antagonists
5.1 Organochlorine, zum Beispiel Camphechlor, Chlordane, Endosulfan, Gamma-HCH, HCH, Heptachlor, Lindane, Methoxychlor5.1 Organochlorines, for example, camphechlor, chlordane, endosulfan, gamma-HCH, HCH, heptachlor, lindane, methoxychlor
5.2 Fiprole, zum Beispiel Acetoprole, Ethiprole, Fipronil, Pyrafluprole, Pyriprole, Vaniliprole5.2 Fiproles, for example acetoprole, ethiprole, fipronil, pyrafluprole, pyriprole, vaniliprole
Chlorid-Kanal-AktivatorenChloride channel activators
6.1 Mectine, zum Beispiel Avermectin, Emamectin, Emamectin-benzoate, Ivermectin, Milbemycin6.1 Mectins, for example avermectin, emamectin, emamectin benzoate, ivermectin, milbemycin
Juvenilhormon-Mimetika, zum Beispiel Diofenolan, Epofenonane, Fenoxycarb, Hydroprene, Kinoprene, Methoprene, Pyriproxifen, TripreneJuvenile hormone mimetics, for example, diofenolan, epofenonans, fenoxycarb, hydroprene, kinoprenes, methoprenes, pyriproxifen, triprene
Ecdysonagonisten/disruptorenEcdysone agonists / disruptors
8.1 Diacylhydrazine, zum Beispiel Chromafenozide, Halofenozide, Methoxyfenozide, Tebufenozide8.1 Diacylhydrazines, for example chromafenozides, halofenozides, methoxyfenozides, tebufenozides
Inhibitoren der ChitinbiosyntheseInhibitors of chitin biosynthesis
9.1 Benzoylharnstoffe, zum Beispiel Bistrifluron, Chlofluazuron, Diflubenzuron, Fluazuron, Flucycloxuron, FIu- fenoxuron, Hexaflumuron, Lufenuron, Novaluron, Noviflumuron, Penfluron, Teflubenzuron, Triflumuron9.1 Benzoylureas, for example bistrifluron, chlorofluazuron, diflubenzuron, fluazuron, flucycloxuron, fenphenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron, triflumuron
9.2 Buprofezin9.2 Buprofezin
9.3 Cyromazine9.3 Cyromazine
Inhibitoren der oxidativen Phosphorylierung, ATP-DisruptorenInhibitors of oxidative phosphorylation, ATP disruptors
10.1 Diafenthiuron10.1 Diafenthiuron
10.2 Organozinnverbindungen, zum Beispiel Azocyclotin, Cyhexatin, Fenbutatin-oxide Entkoppler der oxidativen Phoshorylierung durch Unterbrechung des H-Protongradienten10.2 Organotin compounds, for example azocyclotin, cyhexatin, fenbutatin oxides Decoupling of oxidative phosphorylation by interruption of the H proton gradient
11.1 Pyrrole, zum Beispiel Chlorfenapyr11.1 Pyrroles, for example Chlorfenapyr
11.2 Dinitrophenole, zum Beispiel Binapacyrl, Dinobuton, Dinocap, DNOC11.2 Dinitrophenols, for example binapacyrl, dinobutone, dinocap, DNOC
Seite-I-ElektronentransportinhibitorenSide-I electron transport inhibitors
12.1 METI's, zum Beispiel Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad12.1 METI's, for example Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad
12.2 Hydramethylnon12.2 Hydramethylnone
12.3 Dicofol12.3 Dicofol
Seite-Ü-ElektronentransportinhibitorenPage OB electron transport inhibitors
RotenoneRotenone
Seite-HI-ElektronentransportinhibitorenSide-HI electron transport inhibitors
Acequinocyl, FluacrypyrimAcequinocyl, Fluacrypyrim
Mikrobielle Disruptoren der InsektendarmmembranMicrobial disruptors of insect intestinal membrane
Bacillus thuringiensis-StämmeBacillus thuringiensis strains
Inhibitoren der FettsyntheseInhibitors of fat synthesis
Tetronsäuren, zum Beispiel Spirodiclofen, SpiromesifenTetronic acids, for example spirodiclofen, spiromesifen
Tetramsäuren, zum Beispiel Spirotetramat (CAS-Reg.-No.: 203313-25-1) und 3-(2,5-Dimethylphenyl)-8-methoxy-2 -oxo-1 -azaspiro[4.5]dec-3-en-4-yl ethyl carbonate (alias: Carbonic acid, 3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-l-azaspiro[4.5]dec-3-en-4- yl ethyl ester, CAS-Reg.-No. : 382608-10-8) Carboxamide, zum Beispiel FlonicamidTetramic 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
Oktopaminerge Agonisten, zum Beispiel AmitrazOctopaminergic agonists, for example, amitraz
Inhibitoren der Magnesium-stimulierten ATPase,Inhibitors of magnesium-stimulated ATPase,
Propargitepropargite
Aktivatoren des Ryanodine sensitiven Caclcium-Kanals, wie z.B.Activators of the Ryanodine sensitive Caclcium channel, e.g.
Benzoesäuredicarboxamide, zum Beispiel FlubendiamideBenzoic acid dicarboxamides, for example flubendiamides
Nereistoxin- Analoge, zum Beispiel Thiocyclam hydrogen Oxalate, Thiosultap-sodiumNereistoxin analogs, for example thiocyclam hydrogen oxalate, thiosultap-sodium
Biologika, Hormone oder PheromoneBiologics, hormones or pheromones
Azadirachtin, Bacillus spec, Beauveria spec, Codlemone, Metarrhizium spec, Paecilomyces spec, Thuringiensin, Verticillium spec.Azadirachtin, bacillus spec, beauveria spec, codlemone, metarrhicon spec, paecilomyces spec, thuringiensin, verticillium spec.
Wirkstoffe mit unbekannten oder nicht spezifischen WirkmechanismenActive substances with unknown or non-specific mechanisms of action
23.1 Begasungsmittel, zum Beispiel Aluminium phosphide, Methyl bromide, Sulfuryl fluoride23.1 fumigants, for example aluminum phosphides, methyl bromides, sulfuryl fluorides
23.2 Fraßhemmer, zum Beispiel Cryolite, Flonicamid, Pymetrozine23.2 feed inhibitors, for example cryolites, flonicamide, pymetrozines
23.3 Milbenwachstumsinhibitoren, zum Beispiel Clofentezine, Etoxazole, Hexythiazox23.3 mite growth inhibitors, for example clofentezine, etoxazole, hexythiazox
23.4 Amidoflumet, Benclothiaz, Benzoximate, Bifenazate, Bromopropylate, Buprofezin, Chino- methionat, Chlordimeform, Chlorobenzilate, Chloropicrin, Clothiazoben, Cycloprene, Cyflumetofen, Dicyclanil, Fenoxacrim, Fentrifanil, Flubenzimine, Flufenerim, Flutenzin, Gossyplure, Hydramethylnone, Japonilure, Metoxadiazone, Petroleum, Piperonyl butoxide, Potassium oleate, Pyridalyl, Sulfluramid, Tetradifon, Tetrasul, Tri- arathene,Verbutin Auch eine Mischung mit anderen bekannten Wirkstoffen, wie Herbiziden, Düngemitteln, Wachstumsregulatoren, Safenern, Semiochemicals, oder auch mit Mitteln zur Verbesserung der Pflanzeneigenschaften ist möglich.23.4 Amidoflumet, Benclothiaz, Benzoximate, Bifenazate, Bromopropylate, Buprofezin, Chino-methionate, Chlordimeform, Chlorobenzilate, Chloropicrin, Clothiazoben, Cycloprene, Cyflumetofen, Dicyclanil, Fenoxacrim, Fentrifanil, Flubenzimine, Flufenerim, Flotenzin, Gossyplure, Hydramethylnone, Japonilure, Metoxadiazone, Petroleum , Piperonyl butoxide, Potassium oleate, Pyralidyl, Sulfluramid, Tetradifon, Tetrasul, Tri- arathene, Verbutin A mixture with other known active ingredients, such as herbicides, fertilizers, growth regulators, safeners, semiochemicals, or with agents for improving the plant properties is possible.
Die erfindungsgemäßen Wirkstoffe können ferner beim Einsatz als Insektizide in ihren handels- üblichen Formulierungen sowie in den aus diesen Formulierungen bereiteten Anwendungsformen in Mischung mit Synergisten vorliegen. Synergisten sind Verbindungen, durch die die Wirkung der Wirkstoffe gesteigert wird, ohne daß der zugesetzte Synergist selbst aktiv wirksam sein muß.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.
Die erfindungsgemäßen Wirkstoffe können ferner beim Einsatz als Insektizide in ihren handelsüblichen Formulierungen sowie in den aus diesen Formulierungen bereiteten Anwendungsformen in Mischungen mit Hemmstoffen vorliegen, die einen Abbau des Wirkstoffes nach Anwendung in der Umgebung der Pflanze, auf der Oberfläche von Pflanzenteilen oder in pflanzlichen Geweben vermindern.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 ,
Der Wirkstoffgehalt der aus den handelsüblichen Formulierungen bereiteten Anwendungsformen kann in weiten Bereichen variieren. Die Wirkstoffkonzentration der Anwendungsformen kann von 0,00000001 bis zu 95 Gew.-% Wirkstoff, vorzugsweise zwischen 0,00001 und 1 Gew.-% liegen.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.
Die Anwendung geschieht in einer den Anwendungsformen angepaßten üblichen Weise.The application is done in a custom forms adapted to the application.
Wie bereits oben erwähnt, können erfindungsgemäß alle Pflanzen und deren Teile behandelt werden. In einer bevorzugten Ausführungsform werden wild vorkommende oder durch konventionelle biologische Zuchtmethoden, wie Kreuzung oder Protoplastenfusion erhaltenen Pflanzenarten und Pflanzensorten sowie deren Teile behandelt. In einer weiteren bevorzugten Ausführungsform werden transgene Pflanzen und Pflanzensorten, die durch gentechnologische Methoden gegebenenfalls in Kombination mit konventionellen Methoden erhalten wurden (Genetic Modified Organisms) und deren Teile behandelt. Die Begriffe "Teile" bzw. "Teile von Pflanzen" oder "Pflanzenteile" wurden oben erläutert.As already mentioned above, according to the invention all plants and their parts can be treated. In a preferred embodiment, 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. In a further preferred embodiment, 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.
Besonders bevorzugt werden erfindungsgemäß Pflanzen der jeweils handelsüblichen oder in Gebrauch befindlichen Pflanzensorten behandelt. Unter Pflanzensorten versteht man Pflanzen mit neuen Eigenschaften ("Traits"), die sowohl durch konventionelle Züchtung, durch Mutagenese oder durch rekombinante DNA-Techniken gezüchtet worden sind. Dies können Sorten, Bio- und Genotypen sein.It is particularly preferred according to the invention to treat plants of the respective commercially available or in use plant cultivars. 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.
Je nach Pflanzenarten bzw. Pflanzensorten, deren Standort und Wachstumsbedingungen (Böden, Klima, Vegetationsperiode, Ernährung) können durch die erfindungsgemäße Behandlung auch überadditive ("synergistische") Effekte auftreten. So sind beispielsweise erniedrigte Aufwandmengen und/oder Erweiterungen des Wirkungsspektrums und/oder eine Verstärkung der Wirkung der erfindungsgemäß verwendbaren Stoffe und Mittel, besseres Pflanzenwachstum, erhöhte Toleranz gegenüber hohen oder niedrigen Temperaturen, erhöhte Toleranz gegen Trockenheit oder gegen Wasser- bzw. Bodensalzgehalt, erhöhte Blühleistung, erleichterte Ernte, Beschleunigung der Reife, höhere Ernteerträge, höhere Qualität und/oder höherer Ernährungswert der Ernteprodukte, höhere Lagerfähigkeit und/oder Bearbeitbarkeit der Ernteprodukte möglich, die über die eigentlich zu erwartenden Effekte hinausgehen.Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, diet), the treatment according to the invention may also give rise to superadditive ("synergistic") effects. For example, 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.
Zu den bevorzugten erfϊndungsgemäß zu behandelnden transgenen (gentechnologisch erhaltenen) Pflanzen bzw. Pflanzensorten gehören alle Pflanzen, die durch die gentechnologische Modifikation genetisches Material erhielten, welches diesen Pflanzen besondere vorteilhafte wertvolle Eigenschaften ("Traits") verleiht. Beispiele für solche Eigenschaften sind besseres Pflanzenwachstum, erhöhte Toleranz gegenüber hohen oder niedrigen Temperaturen, erhöhte Toleranz gegen Trockenheit oder gegen Wasser- bzw. Bodensalzgehalt, erhöhte Blühleistung, erleichterte Ernte, Beschleunigung der Reife, höhere Ernteerträge, höhere Qualität und/oder höherer Ernährungswert der Ernteprodukte, höhere Lagerfähigkeit und/oder Bearbeitbarkeit der Ernteprodukte. Weitere und besonders hervorgehobene Beispiele für solche Eigenschaften sind eine erhöhte Abwehr der Pflanzen gegen tierische und mikrobielle Schädlinge, wie gegenüber Insekten, Milben, pflanzenpathogenen Pilzen, Bakterien und/oder Viren sowie eine erhöhte Toleranz der Pflanzen gegen bestimmte herbizide Wirkstoffe. Als Beispiele transgener Pflanzen werden die wichtigen Kulturpflanzen, wie Getreide (Weizen, Reis), Mais, Soja, Kartoffel, Zuckerrüben, Tomaten, Erbsen und andere Gemüsesorten, Baumwolle, Tabak, Raps, sowie Obstpflanzen (mit den Früchten Äpfel, Birnen, Zitrusfrüchten und Weintrauben) erwähnt, wobei Mais, Soja, Kartoffel, Baumwolle, Tabak und Raps besonders hervorgehoben werden. Als Eigenschaften ("Traits") werden besonders hervorgehoben die erhöhte Abwehr der Pflanzen gegen Insekten, Spinnentiere, Nematoden und Schnecken durch in den Pflanzen entstehende Toxine, insbesondere solche, die durch das genetische Material aus Bacillus Thuringiensis (z.B. durch die Gene CryΙA(a), CryIA(b), CryΙA(c), CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb und CrylF sowie deren Kombinationen) in den Pflanzen erzeugt werden (im folgenden "Bt Pflanzen"). Als Eigenschaften ("Traits") werden auch besonders hervorgehoben die erhöhte Abwehr von Pflanzen gegen Pilze, Bakterien und Viren durch Systemische Akquirierte Resistenz (SAR), Systemin, Phytoalexine, Elicitoren sowie Resistenzgene und entsprechend exprimierte Proteine und Toxine. Als Eigenschaften ("Traits") werden weiterhin besonders hervorgehoben die erhöhte Toleranz der Pflanzen gegenüber bestimmten herbiziden Wirkstoffen, beispielsweise Imidazolinonen, Sulfonylharnstoffen, Glyphosate oder Phosphinotricin (z.B. "PAT"-Gen). Die jeweils die gewünschten Eigenschaften ("Traits") verleihenden Gene können auch in Kombinationen miteinander in den transgenen Pflanzen vorkommen. Als Beispiele für "Bt Pflanzen" seien Maissorten, Baumwollsorten, Sojasorten und Kartoffelsorten genannt, die unter den Handelsbezeichnungen YBELD GARD® (Z.B. Mais, Baumwolle, Soja), KnockOut® (z.B. Mais), StarLink® (z.B. Mais), Bollgard® (Baumwolle), Nucotn® (Baumwolle) und NewLeaf® (Kartoffel) vertrieben werden. Als Beispiele für Herbizid-tolerante Pflanzen seien Maissorten, Baumwollsorten und Sojasorten genannt, die unter den Handelsbezeichnungen Roundup Ready® (Toleranz gegen Glyphosate z.B. Mais, Baumwolle, Soja), Liberty Link® (Toleranz gegen Phosphinotricin, z.B. Raps), IMI® (Toleranz gegen Imidazolinone) und STS® (Toleranz gegen Sulfonylharnstoffe z.B. Mais) vertrieben werden. Als Herbizid- resistente (konventionell auf Herbizid-Toleranz gezüchtete) Pflanzen seien auch die unter der Bezeichnung Clearfield® vertriebenen Sorten (z.B. Mais) erwähnt. Selbstverständlich gelten diese Aussagen auch für in der Zukunft entwickelte bzw. zukünftig auf den Markt kommende Pflanzensorten mit diesen oder zukünftig entwickelten genetischen Eigenschaften ("Traits").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"). Examples of such properties 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. Examples of 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. Traits that are particularly emphasized 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 CryΙA (a) , CryIA (b), CryΙA (c), CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF, and combinations thereof) in the plants (hereinafter "Bt plants"). 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 ("traits") can also be combined with one another in combinations with one another transgenic plants occur. Examples of "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). Examples of 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). As herbicide-resistant (grown on conventional herbicide tolerance) plants are also sold under the name Clearfield® varieties (eg corn) mentioned. Of course, these statements also apply to future or future marketed plant varieties with these or future developed genetic traits.
Die aufgeführten Pflanzen können besonders vorteilhaft erfindungsgemäß mit den Verbindungen der allgemeinen Formel I bzw. den erfindungsgemäßen Wirkstoffmischungen behandelt werden. Die bei den Wirkstoffen bzw. Mischungen oben angegebenen Vorzugsbereiche gelten auch für die Behandlung dieser Pflanzen. Besonders hervorgehoben sei die Pflanzenbehandlung mit den im vorliegenden Text speziell aufgeführten Verbindungen bzw. Mischungen.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.
Die erfindungsgemäßen Wirkstoffe wirken nicht nur gegen Pflanzen-, Hygiene- und Vorratsschädlinge, sondern auch auf dem veterinärmedizinischen Sektor gegen tierische Parasiten (Ekto- und Endoparasiten) wie Schildzecken, Lederzecken, Räudemilben, Laufmilben, Fliegen (stechend und leckend), parasitierende Fliegenlarven, Läuse, Haarlinge, Federlinge und Flöhe. Zu diesen Parasiten gehören: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. These parasites include:
Aus der Ordnung der Anoplurida z.B. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp..From the order of the Anoplurida e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.
Aus der Ordnung der Mallophagida und den Unterordnungen Amblycerina sowie Ischnocerina z.B. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp..From the order of Mallophagida and suborders Amblycerina and Ischnocerina, for example. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp.
Aus s der Ordnung Diptera und den Unterordnungen Nematocerina sowie Brachycerina z.B. Aedes spp >., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilυs spp., Hippobosca spp., Lipoptena spp., Melophagus spp..From the order Diptera and the suborders Nematocerina and Brachycerina eg Aedes spp>., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra Spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp. , Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp.
Aus der Ordnung der Siphonapterida z.B. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp..From the order of siphonapterida e.g. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.
Aus der Ordnung der Heteropterida z.B. Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp..From the order of the heteropterid e.g. Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.
Aus der Ordnung der Blattarida z.B. Blatta orientalis, Periplaneta americana, Blattela germanica, Supella spp..From the order of Blattarida e.g. Blatta orientalis, Periplaneta americana, Blattela germanica, Supella spp.
Aus der Unterklasse der Acari (Acarina) und den Ordnungen der Meta- sowie Mesostigmata z.B. Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp..From the subclass of Acari (Acarina) and the orders of Meta and Mesostigmata e.g. Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp ., Sternostoma spp., Varroa spp.
Aus der Ordnung der Actinedida (Prostigmata) und Acaridida (Astigmata) z.B. Acarapis spp., Cheyletiella spp., Ornithocheyletia 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..From the order of Actinedida (Prostigmata) and Acaridida (Astigmata) e.g. Acarapis spp., Cheyletiella spp., Ornithocheyletia 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.
Die erfindungsgemäßen Wirkstoffe der Formel (I) eignen sich auch zur Bekämpfung von Arthropoden, die landwirtschaftliche Nutztiere, wie z.B. Rinder, Schafe, Ziegen, Pferde, Schweine, Esel, Kamele, Büffel, Kaninchen, Hühner, Puten, Enten, Gänse, Bienen, sonstige Haustiere wie z.B. Hunde, Katzen, Stubenvögel, Aquarienfische sowie sogenannte Versuchstiere, wie z.B. Hamster, Meerschweinchen, Ratten und Mäuse befallen. Durch die Bekämpfung dieser Arthropoden sollen Todesfälle und Leistungsminderungen (bei Fleisch, Milch, Wolle, Häuten, Eiern, Honig usw.) vermindert werden, so daß durch den Einsatz der erfindungsgemäßen Wirkstoffe eine wirtschaftlichere und einfachere Tierhaltung möglich ist.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. By controlling these arthropods deaths and reductions in performance (in meat, milk, wool, hides, eggs, honey, etc.) are reduced, so that a more economical and easier animal husbandry is possible by the use of the active compounds according to the invention.
Die Anwendung der erfindungsgemäßen Wirkstoffe geschieht im Veterinärsektor und bei der Tierhaltung in bekannter Weise durch enterale Verabreichung in Form von beispielsweise Tabletten, Kapseln, Tränken, Drenchen, Granulaten, Pasten, BoIi, des feed-through-Verfahrens, von Zäpfchen, durch parenterale Verabreichung, wie zum Beispiel durch Injektionen (intramuskulär, subcutan, intravenös, intraperitonal u.a.), Implantate, durch nasale Applikation, durch dermale Anwendung in Form beispielsweise des Tauchens oder Badens (Dippen), Sprühens (Spray), Aufgießens (Pour-on und Spot-on), des Waschens, des Einpudems sowie mit Hilfe von wirkstoffhaltigen Formkörpern, wie Halsbändern, Ohrmarken, Schwanzmarken, Gliedmaßenbändern, Halftern, Markierungsvorrichtungen usw.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.
Bei der Anwendung für Vieh, Geflügel, Haustiere etc. kann man die Wirkstoffe der Formel (I) als Formulierungen (beispielsweise Pulver, Emulsionen, fließfähige Mittel), die die Wirkstoffe in einer Menge von 1 bis 80 Gew.-% enthalten, direkt oder nach 100 bis 10 000-facher Verdünnung anwenden oder sie als chemisches Bad verwenden.In the application for livestock, poultry, pets, etc., 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.
Außerdem wurde gefunden, daß die erfindungsgemäßen Verbindungen eine hohe insektizide Wirkung gegen Insekten zeigen, die technische Materialien zerstören.In addition, it has been found that the compounds according to the invention show a high insecticidal activity against insects which destroy industrial materials.
Beispielhaft und vorzugsweise - ohne jedoch zu limitieren - seien die folgenden Insekten genannt:By way of example and preferably without limiting however, the following insects are mentioned:
Käfer wie Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthes rugicollis, Xyleborus spec. Tryptodendron spec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec. Dinoderus minutus;Beetles such as Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthes rugicollis, Xyleborus spec. Tryptodendron spec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec. Dinoderus minutus;
Hautflügler wie Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur;Hymenoptera such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur;
Termiten wie Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus;Termites such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus;
Borstenschwänze wie Lepisma saccharina.Bristle tails like Lepisma saccharina.
Unter technischen Materialien sind im vorliegenden Zusammenhang nicht-lebende Materialien zu verstehen, wie vorzugsweise Kunststoffe, Klebstoffe, Leime, Papiere und Kartone, Leder, Holz, Holzverarbeitungsprodukte und Anstrichmittel.Technical materials in the present context are non-living materials, such as preferably plastics, adhesives, glues, papers and cardboard, leather, wood, wood processing products and paints.
Die anwendungsfertigen Mittel können gegebenenfalls noch weitere Insektizide und gegebenenfalls noch ein oder mehrere Fungizide enthalten.The ready-to-use agents may optionally contain further insecticides and optionally one or more fungicides.
Hinsichtlich möglicher zusätzlicher Zumischpartner sei auf die oben genannten Insektizide und Fungizide verwiesen.With regard to possible additional admixing partners, reference is made to the above-mentioned insecticides and fungicides.
Zugleich können die erfindungsgemäßen Verbindungen zum Schutz vor Bewuchs von Gegenständen, insbesondere von Schiffskörpern, Sieben, Netzen, Bauwerken, Kaianlagen und Signalanlagen, welche mit See- oder Brackwasser in Verbindung kommen, eingesetzt werden. Weiter können die erfindungsgemäßen Verbindungen allein oder in Kombinationen mit anderen Wirkstoffen als Antifouling-Mittel eingesetzt werden.At the same time, 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.
Die Wirkstoffe eignen sich auch zur Bekämpfung von tierischen Schädlingen im Haushalts-, Hygiene- und Vorratsschutz, insbesondere von Insekten, Spinnentieren und Milben, die in geschlossenen Räumen, wie beispielsweise Wohnungen, Fabrikhallen, Büros, Fahrzeugkabinen u.a. vorkommen. Sie können zur Bekämpfung dieser Schädlinge allein oder in Kombination mit anderen Wirk- und Hilfsstoffen in Haushaltsinsektizid-Produkten verwendet werden. Sie sind gegen sensible und resistente Arten sowie gegen alle Entwicklungsstadien wirksam. Zu diesen Schädlingen gehören: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:
Aus der Ordnung der Scorpionidea z.B. Buthus occitanus.From the order of Scorpionidea e.g. Buthus occitanus.
Aus der Ordnung der Acarina z.B. Argas persicus, Argas reflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus, Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae.From the order of 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.
Aus der Ordnung der Araneae z.B. Aviculariidae, Araneidae.From the order of the Araneae e.g. Aviculariidae, Araneidae.
Aus der Ordnung der Opiliones z.B. Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, Opiliones phalangium.From the order of Opiliones e.g. Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, Opiliones phalangium.
Aus der Ordnung der Isopoda z.B. Oniscus asellus, Porcellio scaber.From the order of isopods e.g. Oniscus asellus, Porcellio scaber.
Aus der Ordnung der Diplopoda z.B. Blaniulus guttulatus, Polydesmus spp..From the order of diplopoda e.g. Blaniulus guttulatus, Polydesmus spp ..
Aus der Ordnung der Chilopoda z.B. Geophilus spp..From the order of Chilopoda e.g. Geophilus spp ..
Aus der Ordnung der Zygentoma z.B. Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus.From the order of Zygentoma e.g. Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus.
Aus der Ordnung der Blattaria z.B. Blatta orientalies, Blattella germanica, Blattella asahinai, Leucophaea maderae, Panchlora spp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana, Periplaneta brunnea, Periplaneta fuliginosa, Supella longipalpa.From the order of the Blattaria e.g. Blatta orientalies, Blattella germanica, Blattella asahinai, Leucophaea maderae, Panchlora spp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana, Periplaneta brunnea, Periplaneta fuliginosa, Supella longipalpa.
Aus der Ordnung der Saltatoria z.B. Acheta domesticus.From the order of Saltatoria e.g. Acheta domesticus.
Aus der Ordnung der Dermaptera z.B. Forfϊcula auricularia.From the order of the Dermaptera e.g. Forfϊcula auricularia.
Aus der Ordnung der Isoptera z.B. Kalotermes spp., Reticulitermes spp. Aus der Ordnung der Psocoptera z.B. Lepinatus spp., Liposcelis spp.From the order of the Isoptera eg Kalotermes spp., Reticulitermes spp. From the order of Psocoptera eg Lepinatus spp., Liposcelis spp.
Aus der Ordnung der Coleoptera z.B. Anthrenus spp., Attagenus spp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp., Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae, Sitophilus zeamais, Stegobium paniceum.From the order of Coleoptera e.g. Anthrenus spp., Attagenus spp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp., Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae, Sitophilus zeamais, Stegobium paniceum.
Aus der Ordnung der Diptera z.B. 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.From the order of 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.
Aus der Ordnung der Lepidoptera z.B. Achroia grisella, Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.From the order of Lepidoptera e.g. Achroia grisella, Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.
Aus der Ordnung der Siphonaptera z.B. Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.From the order of siphonaptera e.g. Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.
Aus der Ordnung der Hymenoptera z.B. Camponotus herculeanus, Lasius fϊiliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.From the order of Hymenoptera e.g. Camponotus herculeanus, Lasius fϊiliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.
Aus der Ordnung der Anoplura z.B. Pediculus humanus capitis, Pediculus humanus coφoris, Pemphigus spp., Phylloera vastatrix, Phthirus pubis.From the order of the Anoplura e.g. Pediculus humanus capitis, Pediculus humanus coφoris, Pemphigus spp., Phylloera vastatrix, Phthirus pubis.
Aus der Ordnung der Heteroptera z.B. Cimex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans.From the order of Heteroptera, e.g. Cimex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans.
Die Anwendung im Bereich der Haushaltsinsektizide erfolgt allein oder in Kombination mit anderen geeigneten Wirkstoffen wie Phosphorsäureestern, Carbamaten, Pyrethroiden, Neo- nicotinoiden, Wachstumsregulatoren oder Wirkstoffen aus anderen bekannten Insektizidklassen.The application in the field of household insecticides is carried out alone or in combination with other suitable active ingredients such as phosphoric acid esters, carbamates, pyrethroids, neonicotinoids, growth regulators or active compounds from other known classes of insecticides.
Die Anwendung erfolgt in Aerosolen, drucklosen Sprühmitteln, z.B. Pump- und Zerstäubersprays, Nebelautomaten, Foggem, Schäumen, Gelen, Verdampferprodukten mit Verdampferplättchen aus Cellulose oder Kunststoff, Flüssigverdampfern, Gel- und Membranverdampfern, propellergetriebenen Verdampfern, energielosen bzw. passiven Verdampfungssystemen, Mottenpapieren, Mottensäckchen und Mottengelen, als Granulate oder Stäube, in Streuködern oder Köderstationen. Herstellungsbeispiele: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. Preparation Examples:
Herstellungsbeispiele der Vorstufen für die Synthese der Verbindungen der allgemeinen Formel (II)Preparation Examples of the Precursors for the Synthesis of the Compounds of the General Formula (II)
(1): l-(3-Chlor-2,5-dihydroxyphenyl)-ethanon(1): 1- (3-Chloro-2,5-dihydroxyphenyl) -ethanone
Innerhalb von 2 h werden 57 g N-Chlorsuccinimid unter Stickstoff portionsweise zu einer Lösung von 50 g 2,5-Dihydroxypenylaceton in 800 ml DMF gegeben.Within 2 h, 57 g of N-chlorosuccinimide are added in portions under nitrogen to a solution of 50 g of 2,5-dihydroxypenylacetone in 800 ml of DMF.
Die Reaktionslösung verfärbte sich braun und wird über Nacht bei RT gerührt.The reaction solution turned brown and is stirred at RT overnight.
Das Reaktionsgemisch wird in 1,5 1 Wasser gegossen und mit einem Hexan/Ethylacetat Gemisch (1 :1) mehrfach extrahiert. Die vereinten organischen Phasen werden zweimal mit Wasser gewaschen, über Na2SO4 getrocknet, filtriert und zur Trockene eingeengt. Das Rohprodukt wird aus Hexan/Ethylacetat umkristallisiert. Es wurden 20,5 g sauberes l-(3-Chlor-2,5-dihydroxy- phenyl)-ethanon und 28,5 g leicht verunreinigtes Produkt erhalten.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.
M+(ES+)= (187, 100) 1H-NMR(CD3CN): 2,60 (s, 3H, CH3); 6,98 (bs, IH, OH); 7,18 (d, J= 0,3 Hz, IH, Aryl); 7,25 (d, JM + (ES +) = (187, 100) 1 H-NMR (CD 3 CN): 2.60 (s, 3H, CH 3 ); 6.98 (bs, IH, OH); 7.18 (d, J = 0.3Hz, IH, aryl); 7.25 (d, J
= 0,3 Hz, IH, Aryl); 12,22 (s, IH, OH)= 0.3 Hz, IH, aryl); 12.22 (s, IH, OH)
(2): l-(3-Chlor-2-hydroxy-5-triisopropylsilanyloxy-phenyl)-ethanon(2): 1- (3-Chloro-2-hydroxy-5-triisopropylsilanyloxy-phenyl) -ethanone
Zu 5 g l-(3-Chlor-2,5-dihydroxyphenyl)-ethanon in 300 ml Dichlormethan werden 4 g Triethyl- amin und 5,2 g Triisopropylsilylchlorid gegeben und 3 h bei RT gerührt. Das Reaktionsgemisch wird mit Wasser gewaschen, über Na2SO4 getrocknet, filtriert, und zur Trockene eingeengt. Man - -4 g of triethylamine and 5.2 g of triisopropylsilyl chloride are added to 5 g of 1- (3-chloro-2,5-dihydroxyphenyl) -ethanone in 300 ml of dichloromethane and the mixture is stirred at RT for 3 h. The reaction mixture is washed with water, dried over Na 2 SO 4 , filtered, and concentrated to dryness. you - -
erhält 8,28 g (73%-tig laut LC-MS) des l-(3-Chlor-2-hydroxy-5-triisopropylsilanyloxy-phenyl)- ethanon als dunkles Öl. M+(ES+)= (343, 100)receives 8.28 g (73% by LC-MS) of 1- (3-chloro-2-hydroxy-5-triisopropylsilanyloxyphenyl) ethanone as a dark oil. M + (ES +) = (343, 100)
1H-NMR(CD3CN): 1,11 (d, J=7,2 Hz; 9H, CH3, iPr); 1,26-1,33 (m, 3H, CH, iPr); 2,60 (s, 3H, CH3); 7,23 (d, J= 2,9 Hz, IH, Aryl); 7,29 (d, J= 2,9 Hz, IH, Aryl); 12,33 (s, IH, OH). 1 H-NMR (CD 3 CN): 1.11 (d, J = 7.2 Hz; 9H, CH 3 , iPr); 1.26-1.33 (m, 3H, CH, iPr); 2.60 (s, 3H, CH 3 ); 7.23 (d, J = 2.9 Hz, IH, aryl); 7.29 (d, J = 2.9 Hz, IH, aryl); 12.33 (s, IH, OH).
Analog zu (2) wurden folgende Verbindungen hergestellt:Analogously to (2), the following compounds were prepared:
(3) (4) (5)(3) (4) (5)
(3): (3-Chlor-2-hydroxy-5-(triisopropylsilyloxy)-phenyl)-2-methylpropan-l-on(3): (3-Chloro-2-hydroxy-5- (triisopropylsilyloxy) -phenyl) -2-methylpropan-1-one
Durch Umsetzung von 33g l-(3-Chlor-2,5-dihydroxyphenyl)-2-methylpropan-l-on und 31,3g Chlortriisopropylsilan wurden 56g Produkt (93%ig laut LC-MS) eines braunen Öls erhalten. M+(ES+)= (371, 100)By reaction of 33 g of 1- (3-chloro-2,5-dihydroxyphenyl) -2-methylpropan-1-one and 31.3 g of chlorotriisopropylsilane, 56 g of product (93% by LC-MS) of a brown oil were obtained. M + (ES +) = (371, 100)
1H-NMR(DMSO-D6): 1.08 (d, J=7.3Hz, 18H, SMPr3)1.14 (d, J=6.8Hz, 6H, iPr); 1,25 (m, 3H, Si- iPr3); 3.63 (m, IH, iPr); 7.23 (d, J=2.9Hz, IH, Aryl); 7.27 (d, J=2.9Hz, Aryl); 12.0 (s, IH, OH) 1 H-NMR (DMSO-D6): 1:08 (d, J = 7.3Hz, 18H, smpr 3) 1.14 (d, J = 6.8 Hz, 6H, iPr); 1.25 (m, 3H, Si-iPr 3 ); 3.63 (m, IH, iPr); 7.23 (d, J = 2.9Hz, IH, aryl); 7.27 (d, J = 2.9Hz, aryl); 12.0 (s, IH, OH)
(4): (3-Chlor-2-hydroxy-5-(trüsopropylsilyloxy)-phenyl)-cyclopropylketon(4): (3-Chloro-2-hydroxy-5- (triisopropylsilyloxy) -phenyl) -cyclopropyl ketone
Durch Umsetzung von 85g (3-Chlor-2,5-dihydroxyphenyl)-cyclopropylketon und 81g Chlortriisopropylsilan wurden nach kurzer Säulenfϊltration (Cyclohexan-Essigester 5:1) 85g eines braunen Öls als Produkt erhalten. M+(ES+)= (369, 100)By reacting 85 g of (3-chloro-2,5-dihydroxyphenyl) cyclopropyl ketone and 81 g of chlorotriisopropylsilane, 85 g of a brown oil were obtained as product after brief column filtration (5: 1 cyclohexane / ethyl acetate). M + (ES +) = (369, 100)
1H-NMR(DMSO-D6): 1.08 (d, J=7.3Hz, 18H, -iPr); 1.09 (m, 4H, -cPr); 1.26 (m, 3H, -iPr); 2.17(m, IH, -cPr); 7.24 (d, J=2.9Hz, IH, Aryl); 7.27 (d, J=2.9Hz, Aryl); 11.85 (s, IH, OH) 1 H-NMR (DMSO-D 6 ): 1.08 (d, J = 7.3Hz, 18H, -iPr); 1.09 (m, 4H, -cPr); 1.26 (m, 3H, -iPr); 2.17 (m, IH, -cPr); 7.24 (d, J = 2.9Hz, IH, aryl); 7.27 (d, J = 2.9Hz, aryl); 11.85 (s, IH, OH)
(5): (S-Chlor^-hydroxy-S-ftriisopropylsilyloxy^-phenyty-cyclohexylketon(5): (S-chloro-hydroxy-S-triisopropylsilyloxy-phenyl-cyclohexyl ketone
Durch Umsetzung von 33g (3-Chlor-2,5-dihydroxyphenyl)-cyclohexylketon und 31,3g Chlortriisopropylsilan wurden 56g eines braunen Öls als Rohprodukt erhalten, welches ohne Aufreinigung im nächsten Schritt eingesetzt wurde. - -By reaction of 33 g (3-chloro-2,5-dihydroxyphenyl) cyclohexyl ketone and 31.3 g of chlorotrisopropylsilane, 56 g of a brown oil were obtained as crude product, which was used without purification in the next step. - -
M+(ES+)= (411, 100)M + (ES +) = (411, 100)
1H-NMR(DMSO-D6): 1.08 (d, J=7.3Hz, 18H, -iPr); 1.24 (m, 3H, -iPr); 1.33 (m, 2H, -cHex); 2.58- 1 H-NMR (DMSO-D 6 ): 1.08 (d, J = 7.3Hz, 18H, -iPr); 1.24 (m, 3H, -iPr); 1.33 (m, 2H, -hex); 2.58-
2.83 (bm, 8H, cHex); 2.72 (m, IH, -cHex); 7.25 (m, 2H, Aryl); 12.0 (s, IH, OH)2.83 (bm, 8H, cHex); 2.72 (m, IH, -cHex); 7.25 (m, 2H, aryl); 12.0 (s, IH, OH)
(6) : l-(3-Chlor-5-hydroxy-2-methoxy-phenyl)-ethanon(6): 1- (3-chloro-5-hydroxy-2-methoxy-phenyl) -ethanone
15 g l-(3-Chlor-2-hydroxy-5-triisopropylsilanyloxy-phenyl)-ethanon werden in 250 ml DMF zusammen mit 24 g Kaliumcarbonat und 24,8 g Dimethylsulfat für ca. 5 h bei RT gerührt. Das Reaktionsgemisch wird filtriert und der Rückstand wird mit Dichlormethan nachgewaschen. Die vereinten organischen Phasen werden auf Wasser gegossen, 30 min nachgerührt und dreimal mit Dichlormethan extrahiert, über Na2SO4 getrocknet, filtriert und zur Trockene eingeengt.15 g of 1- (3-chloro-2-hydroxy-5-triisopropylsilanyloxyphenyl) -ethanone are stirred in 250 ml of DMF together with 24 g of potassium carbonate and 24.8 g of dimethyl sulfate for about 5 h at RT. The reaction mixture is filtered and the residue is washed with dichloromethane. The combined organic phases are poured into water, stirred for 30 min and extracted three times with dichloromethane, dried over Na 2 SO 4 , filtered and concentrated to dryness.
Das Rohprodukt wird in 250 ml Ethanol aufgenommen, mit IN-NaOH versetzt und mehrere Stunden unter Rückfiuss gerührt, bis nach DC-Kontrolle der Umsatz vollständig war. Der Ansatz wird zur Trockene aufkonzentiert, der Rückstand mit Wasser versetzen, mit HCl auf pH<7 gebracht und mehrfach mit EE extrahiert, über Na2SO4 getrocknet, filtriert' und zur Trockene einrotiert. Das Rohprodukt wird durch Flashchromatographie über Silica Gel gereinigt (Gradient: Hexan/Ethylacetat 4:1 zu Ethylacetat 100%). Man erhält zwei Fraktionen des Produkts, 4,6 g (100%-tige Reinheit laut LC-MS) und 1,3 g (95%-tige Reinheit laut LC-MS). M+(ES+)= (201, 100) 1H-NMR: 2,67 (s, 3H, CH3); 3,85 (s, 3H, OCH3); 6,21 (s, IH, OH); 7,11 (d, J= 6,2 Hz, IH, Aryl); 7, 12 (d, J= 6,2 Hz, 1 H, Aryl) Analog zu (6) wurden folgende Verbindungen hergestellt: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). M + (ES +) = (201, 100) 1 H NMR: 2.67 (s, 3H, CH 3 ); 3.85 (s, 3H, OCH 3 ); 6.21 (s, IH, OH); 7.11 (d, J = 6.2 Hz, IH, aryl); 7, 12 (d, J = 6.2 Hz, 1H, aryl) Analogously to (6), the following compounds were prepared:
(7) (8) (9)(7) (8) (9)
(7): (3-Chlor-5-hydroxy-2-methoxy-phenyl)-2-methylpropan-l-on(7): (3-chloro-5-hydroxy-2-methoxyphenyl) -2-methylpropan-1-one
Durch Umsetzung von 56.2g (3-Chlor-2-hydroxy-5-(triisopropylsilyloxy)-phenyl)-2-methylpropan- 1-on und 28.6mL Dimethylsulfat wurde ein braunes Öl erhalten, welches mit 150 mL 2N Natronlauge und 300 mL Ethanol mehrere Stunden unter Rückfluss gerührt und nach wässriger Aufarbeitung über Kieselgel (Cyclohexan-Ethylacetat 5:1) chromatographiert wurde. Es wurden 21,6g eines orangefarbenen Öls (GC-Reinheit 71%) erhalten. M+(ES+)= (229, 100)By reaction of 56.2 g (3-chloro-2-hydroxy-5- (triisopropylsilyloxy) -phenyl) -2-methylpropan-1-one and 28.6 mL dimethyl sulfate, a brown oil was obtained which was treated with 150 mL 2N sodium hydroxide solution and 300 mL ethanol Stirred under reflux for several hours and after aqueous work-up on silica gel (cyclohexane-ethyl acetate 5: 1) was chromatographed. There were obtained 21.6 g of an orange oil (GC purity 71%). M + (ES +) = (229, 100)
1H-NMR(DMSO-D6): 1.07 (d, J=6.9Hz, 6H, -iPr); 3.26 (m, IH, -iPr); 3.68 (s, 3H, -OMe); 6.75 (d, J=2.9Hz, IH, Aryl); 6.98 (d, J=2.9Hz, Aryl); 9.88 (s, IH, OH) 1 H-NMR (DMSO-D 6 ): 1.07 (d, J = 6.9Hz, 6H, -iPr); 3.26 (m, IH, -iPr); 3.68 (s, 3H, -OMe); 6.75 (d, J = 2.9Hz, IH, aryl); 6.98 (d, J = 2.9Hz, aryl); 9.88 (s, IH, OH)
(8) : (3-Chlor-5-hydroxy-2-methoxy-phenyl)-cyclopropylketon(8): (3-chloro-5-hydroxy-2-methoxy-phenyl) -cyclopropyl ketone
Durch Umsetzung von 85g (3-Chlor-2-hydroxy-5-(triisopropylsilyloxy)-phenyl)-cyclopropylketon und 58g Dimethylsulfat wurde ein braunes Öl erhalten, welches mit 290 mL 2N NaOH und 500 mL Ethanol mehrere Stunden rückflussiert und nach wässriger Aufarbeitung an KieselgelBy reaction of 85 g (3-chloro-2-hydroxy-5- (triisopropylsilyloxy) phenyl) cyclopropyl ketone and 58 g of dimethyl sulfate, a brown oil was obtained which refluxed with 290 ml of 2N NaOH and 500 ml of ethanol for several hours and after aqueous workup silica gel
(Cyclohexan-Essigester 5:1) chromatographiert wurde. Es wurden 15.3g eines orangefarbenen Öls erhalten.(Cyclohexane-ethyl acetate 5: 1) was chromatographed. 15.3 g of an orange oil were obtained.
M+(ES+)= (227, 100) 1H-NMR(DMSO-D6): 1.07 (d, J=6.2 Hz, 4H, -cPr); 2.61 (m, IH, -cPr); 3.72 (s, 3H,M + (ES +) = (227, 100) 1 H-NMR (DMSO-D 6 ): 1.07 (d, J = 6.2 Hz, 4H, -cPr); 2.61 (m, IH, -cPr); 3.72 (s, 3H,
-OMe); 6.84 (d, J=3Hz, Aryl); 7.02 (d, J=3Hz, Aryl); 9.92 (s, IH, OH)-OMe); 6.84 (d, J = 3Hz, aryl); 7.02 (d, J = 3Hz, aryl); 9.92 (s, IH, OH)
(9): (S-Chlor-S-hydroxy-Z-methoxy-pheny^-cyclohexylketon(9): (S-chloro-S-hydroxy-Z-methoxy-phenyl-cyclohexyl ketone
Durch Umsetzung von 83g (3-Chlor-2-hydroxy-5-(triisoρropylsilyloxy)-phenyl)-cyclohexylketon und 51g Dimethylsulfat wurde ein braunes Öl erhalten, welches mit 200 mL 2N NaOH und 400 mL Ethanol mehrere Stunden rückflussiert und nach wässriger Aufarbeitung an Kieselgel (Cyclohexan-Essigester 5:1) chromatographiert wurde. Es wurden 12g eines orangeroten Öls erhalten. M+(ES+)= (269, 100)By reaction of 83 g (3-chloro-2-hydroxy-5- (triisoρropylsilyloxy) phenyl) cyclohexyl ketone and 51 g of dimethyl sulfate, a brown oil was obtained which refluxed with 200 mL 2N NaOH and 400 mL of ethanol for several hours and after aqueous workup Silica gel (cyclohexane-ethyl acetate 5: 1) was chromatographed. 12g of orange-red oil was obtained. M + (ES +) = (269, 100)
1H-NMR(DMSO-D6): 1.11-1.33 (bm, 4H, -cHex); 1.54-1.82 (bm, 6H, -cHex); 2.99 (m, IH, -cHex); 1 H-NMR (DMSO-D 6 ): 1.11-1.33 (bm, 4H, -cHex); 1.54-1.82 (bm, 6H, -hex); 2.99 (m, IH, -hex);
3.68 (s, 3H, -OMe); 6.72 (d, J=2.9 Hz, Aryl); 6.96 (d, J=2.9 Hz, Aryl); 9.92 (s, IH, OH) 3.68 (s, 3H, -OMe); 6.72 (d, J = 2.9 Hz, aryl); 6.96 (d, J = 2.9 Hz, aryl); 9.92 (s, IH, OH)
Herstellungsbeispiele für Verbindungen der allgemeinen Formel (II)Preparation Examples of Compounds of General Formula (II)
(10): l-[3-Chlor-5-(3,3-dichlor-allyloxy)-2-hydroxy-phenyl]-ethanon(10): 1- [3-chloro-5- (3,3-dichloroallyloxy) -2-hydroxy-phenyl] -ethanone
Zu 8,6 g Kaliumcarbonat in 200 ml abs. Dimethylformamid werden unter Stickstoff 5 g l-(3- Chlor-2,5-dihydroxy-phenyl)-ethanon zugegeben. Anschließend werden 4,7 g Dichlorpropenyl- bromid unter heftigem Rühren als Lösung in 10 ml DMF zugetropft und weitere 5 h bei RT gerührt. Der Ansatz wird in ca. 200 ml Wasser gegossen, mehrfach mit Ethylacetat extrahiert, die organische Phase wird mit Wasser gewaschen, über Na2SO4 getrocknet, filtriert und zur Trockene eingeengt. Man erhält 7,5 g (97%-tig laut LC-MS) von l-[3-Chlor-5-(3,3-dichlor-allyloxy)-2- hydroxy-phenyl]-ethanon als zähflüssiges Öl. M+ (ES+)= (309, 100)To 8.6 g of potassium carbonate in 200 ml of abs. To dimethylformamide are added under nitrogen 5 g of 1- (3-chloro-2,5-dihydroxyphenyl) -ethanone. Thereafter, 4.7 g of dichloropropenyl bromide are added dropwise with vigorous stirring as a solution in 10 ml of DMF and the mixture is stirred at RT for a further 5 h. The mixture is poured into about 200 ml of water, extracted several times with ethyl acetate, the organic phase is washed with water, dried over Na 2 SO 4 , filtered and concentrated to dryness. This gives 7.5 g (97% strength according to LC-MS) of 1- [3-chloro-5- (3,3-dichloroallyloxy) -2-hydroxy-phenyl] -ethanone as a viscous oil. M + (ES +) = (309, 100)
1H-NMR(CDCl3): 2,65 (s, 3H, CH3); 3,85 (s, 3H, OCH3); 4,62 (d, J= 6,3 Hz, 2H, CH2); 6,12 (t, IH, J= 6,3 Hz, IH, CH); 7,05 (d, J= 3,2 Hz, IH, CH Aryl); 7,1 (d, J= 3,2 Hz, IH, CH Aryl) 1 H-NMR (CDCl3): 2.65 (s, 3H, CH 3); 3.85 (s, 3H, OCH 3 ); 4.62 (d, J = 6.3 Hz, 2H, CH 2 ); 6.12 (t, IH, J = 6.3 Hz, IH, CH); 7.05 (d, J = 3.2 Hz, IH, CH aryl); 7.1 (d, J = 3.2 Hz, IH, CH aryl)
Analog der Vorschrift zu l-[3-Chlor-5-(3,3-dichlor-allyloxy)-2-hydroxy-phenyl]-ethanon (10) wurden folgende Verbindungen hergestellt:Analogously to the procedure for 1- [3-chloro-5- (3,3-dichloroallyloxy) -2-hydroxy-phenyl] -ethanone (10), the following compounds were prepared:
Herstellungsbeispiele für Verbindungen der allgemeinen Formel (III)Preparation Examples of Compounds of General Formula (III)
(14): l-[3-Chlor-5-(3,3-dichlor-allyloxy)-2-methoxy-phenyl]-2-methyl-propan-l-on oxim(14): 1- [3-Chloro-5- (3,3-dichloroallyloxy) -2-methoxy-phenyl] -2-methylpropane-l-one oxime
Ig l-[3-Chlor-5-(3,3-dichlor-allyloxy)-2-methoxy-phenyl]-2-methyl-propan-l-on werden zusammen mit 1,44 g Hydroxylamoniumchlorid und 1,7 g Natriumacetat in 10 ml Ethanol für ca. 3 Stunden unter Rückfluss gerührt. Das Reaktionsgemisch wird zur Trockene eingeengt, der Rückstand mehrfach mit Ethylacetat extrahiert, die vereinten organischen Phasen über Natriumsulfat getrocknet, filtriert und zur Trockene eingeengt. Man erhält 1,06 g l-[3-Chlor-5-(3,3-dichlor- allyloxy)-2-methoxy-phenyl]-2-methyl-propan-l-on oxim als E/Z-Isomerengemisch. M+(ES+)= (352, 100)Ig I- [3-chloro-5- (3,3-dichloroallyloxy) -2-methoxy-phenyl] -2-methyl-propan-1-one are added together with 1.44 g of hydroxylammonium chloride and 1.7 g of sodium acetate stirred in 10 ml of ethanol for about 3 hours under reflux. The reaction mixture is concentrated to dryness, the residue extracted several times with ethyl acetate, the combined organic phases over sodium sulfate dried, filtered and concentrated to dryness. This gives 1.06 g of 1- [3-chloro-5- (3,3-dichloroallyloxy) -2-methoxyphenyl] -2-methylpropan-1-one oxime as E / Z isomer mixture. M + (ES +) = (352, 100)
1H-NMR(CD3CN): 1,03 (m, 12 Hz, 4xCH3) iPr); 2,67-2,74 (m, IH, CH, iPr); 3,28-3,41 (m, IH, CH, iPr); 3,71 (s, 3H, OCH3); 3,72 (s, 3H, OCH3); 4,64 (d, J= 6,4 Hz, 2H, CH2CHCCl2); 4,65 (d, J= 6,4 Hz, 2H, CH2CHCCl2); 6,25 (t, J= 6,4 Hz, 2H, 2X CH2CHCCl2); 6,54 (d, J= 3,0 Hz, Aryl); 6,63 (d, J= 3,0 Hz, Aryl); 7,00 (d, J= 3,0 Hz, Aryl); 7,03 (d, J= 3,0 Hz, Aryl). 1 H-NMR (CD 3 CN): 1.03 (m, 12 Hz, 4xCH 3) iPr); 2.67-2.74 (m, IH, CH, iPr); 3.28-3.41 (m, IH, CH, iPr); 3.71 (s, 3H, OCH 3 ); 3.72 (s, 3H, OCH 3 ); 4.64 (d, J = 6.4 Hz, 2H, CH 2 CHCCl 2 ); 4.65 (d, J = 6.4 Hz, 2H, CH 2 CHCCl 2 ); 6.25 (t, J = 6.4Hz, 2H, 2X CH 2 CHCCl 2 ); 6.54 (d, J = 3.0 Hz, aryl); 6.63 (d, J = 3.0 Hz, aryl); 7.00 (d, J = 3.0 Hz, aryl); 7.03 (d, J = 3.0 Hz, aryl).
Analog der Vorschrift von l-[3-ChIor-5-(3,3-dichlor-aHyloxy)-2-methoxy-phenyI]-2-methyl- propan-1-on oxim (14) wurden folgende Verbindungen hergestellt:Analogously to the instructions of 1- [3-chloro-5- (3,3-dichloro-aHyloxy) -2-methoxy-phenyl] -2-methyl-propan-1-one oxime (14), the following compounds were prepared:
(17): l-[3-Chlor-5-(3,3-dichIor-aIlyloxy)-2-methoxy-phenyl]-ethanon oxim (17): 1- [3-Chloro-5- (3,3-dichloro-alyloxy) -2-methoxy-phenyl] -ethanone oxime
Zu 1 g 2-Methoxy-3-chlor-5-dichlθφropenoxybenzaceton in 4,3 ml Ethanol gibt man 2,2 g wässrige Hydroxylamin-Lösung (50% tig) und erhitzt für 2 Stunden auf 70 0C. Man lässt auf RT Abkühlen, die entstandene Suspension wird filtriert, der Feststoff in Dichlormethan gelöst, über Natriumsulfat getrocknet, filtriert und zur Trockene eingeengt. Man erhält 824 mg des l-[3-Chlor- 5-(3,3-dichlor-allyloxy)-2-methoxy-phenyl]-ethanon oxims als E/Z-Isomere im Verhältnis 20:1. M+(ES+)= (324, 100)2.2 g of aqueous hydroxylamine solution (50% strength) are added to 1 g of 2-methoxy-3-chloro-5-dichloro-propenoxybenzacetone in 4.3 ml of ethanol and the mixture is heated to 70 ° C. for 2 hours. The mixture is allowed to cool to RT , the resulting suspension is filtered, the solid dissolved in dichloromethane, dried over sodium sulfate, filtered and concentrated to dryness. 824 mg of the 1- [3-chloro-5- (3,3-dichloroallyloxy) -2-methoxyphenyl] ethanone oxime are obtained as E / Z isomers in the ratio 20: 1. M + (ES +) = (324, 100)
IH-NMR(CD3CN): 3,70 (s, 3H, OCH3); 4,64 (d, J= 6,4 Hz, 2H, CH2CHCCl2); 6,26 (t, J= 6,4 Hz, IH, CH2CHCCl2); 6,79 (d, J= 3,0 Hz, IH, Aryl); 7,03 (d, J= 3,0 Hz, IH, Aryl); 9,05 (s, IH, OH).IH-NMR (CD 3 CN): 3.70 (s, 3H, OCH 3); 4.64 (d, J = 6.4 Hz, 2H, CH 2 CHCCl 2 ); 6.26 (t, J = 6.4 Hz, IH, CH 2 CHCCl 2 ); 6.79 (d, J = 3.0 Hz, IH, aryl); 7.03 (d, J = 3.0 Hz, IH, aryl); 9.05 (s, IH, OH).
Das Filtrat wird zur Trockene eingeengt, der Rückstand zweimal ca. 50 ml Dichlormethan extrahiert, über Natriumsulfat getrocknet, filtriert, und zur Trockene eingeengt. Man erhält 209 mg des l-[3-Chlor-5-(3,3-dichlor-allyloxy)-2-methoxy-phenyl]-ethanon oxims als E/Z-Isomere im Verhältnis 1:1. M+(ES+)= (324, 100)The filtrate is concentrated to dryness, the residue twice extracted about 50 ml of dichloromethane, dried over sodium sulfate, filtered, and concentrated to dryness. This gives 209 mg of 1- [3-chloro-5- (3,3-dichloroallyloxy) -2-methoxyphenyl] ethanone oxime as E / Z isomers in a ratio of 1: 1. M + (ES +) = (324, 100)
(18): l-[3-Chlor-5-(3,3-dichlor-allyloxy)-2-methoxy-phenyl]-ethanon-O-(2-hydroxy-ethyl)- oxim(18): 1- [3-Chloro-5- (3,3-dichloroallyloxy) -2-methoxy-phenyl] -ethanone O- (2-hydroxyethyl) oxime
400 mg l-[3-Chlor-5-(3,3-dichlor-allyloxy)-2-hydroxy-phenyl]-ethanon werden zusammen mit 510 mg Kaliumcarbonat und 700 mg 2-Chlorethanol für 90 min unter Stickstoff bei 1000C gerührt. Es werden weitere 345 mg 2-Chlorethanol zugegeben und weitere 4 h bei 1000C gerührt. Es wird mit ca. 10 ml Wasser versetzt, 2 x mit ca. 50 ml Dichlormethan extrahiert, die vereinten organischen Phasen über Na2SO4 getrocknet, filtriert, und zur Trockene eingeengt. Man erhält 560 mg des l-[3-Chlor-5-(3,3-dichlor-allyloxy)-2-methoxy-phenyl]-ethanon-O-(2-hydroxy-ethyl)- oxims. M+(ES+)= (368, 25)400 mg of 1- [3-chloro-5- (3,3-dichloroallyloxy) -2-hydroxy-phenyl] -ethanone are together with 510 mg of potassium carbonate and 700 mg of 2-chloroethanol for 90 min under nitrogen at 100 ° C. touched. A further 345 mg of 2-chloroethanol are added and the mixture is stirred at 100 ° C. for a further 4 h. It is mixed with about 10 ml of water, extracted 2 x with about 50 ml of dichloromethane, the combined organic phases over Na 2 SO 4 dried, filtered, and concentrated to dryness. This gives 560 mg of 1- [3-chloro-5- (3,3-dichloroallyloxy) -2-methoxyphenyl] ethanone O- (2-hydroxyethyl) oxime. M + (ES +) = (368, 25)
Analog zu (18) wurde folgende Verbindung synthetisiert:Analogously to (18), the following compound was synthesized:
Herstellungsbeispiele für Verbindungen der allgemeinen Formel (I)Preparation Examples of Compounds of General Formula (I)
(20) l-ß-Chlor-S-ß^-dichlor-allyloxy^-methoxy-phenyll-ethanon-O-ß-ß-chlor-S- trifluormethyl-pyridin-2-yloxy)-ethyll-oxim(20) 1-.beta.-chloro-S-.beta.-dichloro-allyloxy-3-methoxy-phenyl-ethanone-O-.beta.-.beta.-chloro-S-trifluoromethyl-pyridin-2-yloxy) -ethyl-oxime
250 mg 1 -[3-Chlor-5-(3,3-dichlor-allyloxy)-2-methoxy-phenyl]-ethanon-O-(2-hydroxy-ethyl)- oxim, 133 mg 2-Hydroxy-5-trifluormethylpyridin und 355 mg Triphenylphosphin werden zusammen in 15 ml abs. Tetrahydrofuran vorgelegt. 236 mg DEAD werden als Lösung in 1 ml Tetrahydrofuran zugetropft. Man lässt über Nacht bei RT rühren. Das Reaktionsgemisch wird zur Trockene eingeengt und das Rohprodukt über HPLC gereinigt. Man erhält 6 mg des l-[3-Chlor-5- (3,3-dichlor-allyloxy)-2-methoxy-phenyl]-ethanon-0-[2-(3-chlor-5-trifluoromethyl-pyridin-2- yloxy)-ethyl]-oxims. M+(ES+)= (547, 80)250 mg of 1 - [3-chloro-5- (3,3-dichloroallyloxy) -2-methoxyphenyl] ethanone O- (2-hydroxyethyl) oxime, 133 mg 2-hydroxy-5- trifluoromethylpyridine and 355 mg of triphenylphosphine together in 15 ml of abs. Submitted tetrahydrofuran. 236 mg of DEAD are added dropwise as a solution in 1 ml of tetrahydrofuran. It is allowed to stir overnight at RT. The reaction mixture is concentrated to dryness and the crude product purified by HPLC. This gives 6 mg of 1- [3-chloro-5- (3,3-dichloroallyloxy) -2-methoxyphenyl] ethanone 0- [2- (3-chloro-5-trifluoromethyl-pyridine-2 - yloxy) -ethyl] oxime. M + (ES +) = (547, 80)
1H-NMR(CDCl3): 2,20 (s, 3H, CH3); 3,74 (s, 3H, OCH3); 4,56 (dd, J= 4,6; J= 5,1; 2H, CH2); 4,61 (d, J= 6,3 Hz, CH2CHCCl2); 4,75 (dd, J= 4,6; J= 5,1; 2H, CH2); 6,12 (t, J= 6,3 Hz, IH, CH2CHCCl2); 6,77 (d, J= 3,1 Hz, IH, Aryl); 6,94 (d, J= 3,1 Hz, IH, Aryl); 7,85 (d, J= 2,1 Hz; IH, Pyridyl); 8,31 (d, J= 1,2 Hz, IH, Pyridyl). 1 H-NMR (CDCl3): 2.20 (s, 3H, CH 3); 3.74 (s, 3H, OCH 3 ); 4.56 (dd, J = 4.6, J = 5.1, 2H, CH 2 ); 4.61 (d, J = 6.3 Hz, CH 2 CHCCl 2 ); 4.75 (dd, J = 4.6, J = 5.1, 2H, CH 2 ); 6.12 (t, J = 6.3 Hz, IH, CH 2 CHCCl 2 ); 6.77 (d, J = 3.1 Hz, IH, aryl); 6.94 (d, J = 3.1 Hz, IH, aryl); 7.85 (d, J = 2.1 Hz, IH, pyridyl); 8.31 (d, J = 1.2 Hz, IH, pyridyl).
Analog der Vorschrift zu l-[3-Chlor-5-(3,3-dichlor-allyloxy)-2-methoxy-phenyl]-ethanon-0- [2-(3-chlor-5-trifluoromethyl-pyridin-2-yloxy)-ethylJ-oxim (20) wurden folgende Verbindungen der allgemeinen Formel I synthetisiert:Analogously to the procedure for 1- [3-chloro-5- (3,3-dichloroallyloxy) -2-methoxyphenyl] ethanone 0- [2- (3-chloro-5-trifluoromethylpyridine-2-one yloxy) -ethylJ-oxime (20), the following compounds of general formula I were synthesized:
(D(D
- - - -
Tabelle 1 für X= OTable 1 for X = O
Variante zur Herstellung der Verbindung (27:)Variant for the preparation of the compound (27 :)
Die Synthese der Aminoetherseitenketten ist in DE 10301519 Al beschrieben.The synthesis of the amino ether side chains is described in DE 10301519 A1.
(25): 3-{[5-(Trifluormethyl)pyτidin-2-yl]oxy}propan-l-ol(25): 3 - {[5- (trifluoromethyl) pyidin-2-yl] oxy} propan-1-ol
Zu einer Suspension von 4 g Natriumhydrid in 100 ml DMF werden 12,6 g 1,3-Propandiol gegeben. Nach beendeter Gasentwicklung wird ca. 10 min bei Raumtemperatur nachgerührt.To a suspension of 4 g of sodium hydride in 100 ml of DMF, 12.6 g of 1,3-propanediol are added. After completion of gas evolution is stirred for about 10 min at room temperature.
Anschließend werden 10 g 2-Chlor-5-trifluorrnethylpyridin als Lösung in 10 ml DMF zugegeben und über Nacht bei Raumtemperatur gerührt. Das Reaktionsgemisch wird In Wasser gegossen und dreimal mit Dichlormethan extrahiert. Die vereinigten organischen Phasen werden über Natriumsulfat getrocknet, filtriert und zur Trockene eingeengt. Das Rohprodukt wird in Toluol aufgenommen, mit Wasser gewaschen, über Natriumsulfat getrocknet, filtriert und zur Trockene eingeengt.Subsequently, 10 g of 2-chloro-5-trifluoromethylpyridine are added as a solution in 10 ml of DMF and stirred overnight at room temperature. The reaction mixture is poured into water and extracted three times with dichloromethane. The combined organic phases are dried over sodium sulfate, filtered and concentrated to dryness. The crude product is taken up in toluene, washed with water, dried over sodium sulfate, filtered and concentrated to dryness.
Der ölige Rückstand wird mit Pentan verrührt. Und im Tiefkühlschrank zur Kristallisation gebracht. Der Ausgefallene Feststoff wird über eine Fritte abfiltriert, mit Pentan gewaschen und im Vakuum getrocknet. Man erhält 5,2 g 3-{[5-(Trifluormethyl)pyridin-2-yl]oxy}propan-l-ol. M+(ES+)= (222, 100)The oily residue is stirred with pentane. And brought to crystallization in the freezer. The precipitated solid is filtered through a frit, washed with pentane and dried in vacuo. This gives 5.2 g of 3 - {[5- (trifluoromethyl) pyridin-2-yl] oxy} propan-1-ol. M + (ES +) = (222, 100)
1H-NMR(CDCl3): 2,02 (dt, 2H, CH2); 3,75 (t, J= 6 Hz, 2H, CH2); 4,55 (t, J= 6 Hz, 2H, CH2); 6,82 (d, J= 8,8 Hz, IH, CH, Pyridyl); 7,78 (dd, J= 8,8 Hz, J= 2,5 Hz, IH, CH, Pyridyl); 8,42 (s, IH, CH, Pyridyl). 1 H-NMR (CDCl3): 2.02 (dt, 2H, CH 2); 3.75 (t, J = 6 Hz, 2H, CH 2 ); 4.55 (t, J = 6 Hz, 2H, CH 2 ); 6.82 (d, J = 8.8 Hz, IH, CH, pyridyl); 7.78 (dd, J = 8.8 Hz, J = 2.5 Hz, IH, CH, pyridyl); 8.42 (s, IH, CH, pyridyl).
(26) : l-(3- { [5-(Trifluormethyl)pyridin-2-yl] oxy} propoxy)pyrrolidin-2,5-dion(26): 1- (3- {[5- (trifluoromethyl) pyridin-2-yl] oxy} propoxy) pyrrolidine-2,5-dione
Unter Stickstoff werden 2,5 g 3-{[5-(Trifluormethyl)pyridin-2-yl]oxy}propan-l-ol zusammen mit 1,3 g N-Hydroxylphthalimid und 2,96 g Triphenylphosphin in 200 ml abs. Tetrahydrofuran gerührt. Bei 0 0C werden 1,97 g Diethylazodicarboxylat zugetropft und über Nacht bei Raumtemperatur gerührt. Das Reaktionsgemisch wird zur Trockene eingeengt und aus Hexan/EE 4:1 umkristallisiert. Der erhaltene Feststoff wird erneut in heißem Isopropanol gelöst und im Kühlschrank zur Kristallisation gebracht. Man erhält 3,25 g l-(3-{[5(Trifluor-methyl)pyridin-2- yl]oxy}propoxy)pyrrolidin-2,5-dion als farblosen Feststoff. M+(ES+)= (319, 100)Under nitrogen, 2.5 g of 3 - {[5- (trifluoromethyl) pyridin-2-yl] oxy} propan-1-ol together with 1.3 g of N-hydroxylphthalimide and 2.96 g of triphenylphosphine in 200 ml of abs. Stirred tetrahydrofuran. At 0 ° C., 1.97 g of diethyl azodicarboxylate are added dropwise and the mixture is stirred overnight at room temperature. The reaction mixture is concentrated to dryness and recrystallized from hexane / EA 4: 1. The resulting solid is redissolved in hot isopropanol and crystallized in the refrigerator. 3.25 g of 1- (3 - {[5 (trifluoro-methyl) -pyridin-2-yl] oxy} -propoxy) -pyrrolidine-2,5-dione are obtained as a colorless solid. M + (ES +) = (319, 100)
1H-NMR(CDCl3): 2,10 (dt, 2H, CH2); 3,13 (s, 4H, CH2); 4,16 (t, J= 6,3 Hz, 2H, CH2); 4,51 (t, J= 6,4 Hz, 2H, CH2); 6,99 (d, J= 8,7 Hz, IH, CH, Pyridyl); 8,01 (dd, J= 8,8 Hz, J= 6,5 Hz, IH, CH Pyridyl); 8,54 (s, IH, CH, Pyridyl) 1 H-NMR (CDCl3): 2.10 (dt, 2H, CH2); 3.13 (s, 4H, CH2); 4.16 (t, J = 6.3 Hz, 2H, CH 2); 4.51 (t, J = 6.4 Hz, 2H, CH2); 6.99 (d, J = 8.7 Hz, IH, CH, pyridyl); 8.01 (dd, J = 8.8 Hz, J = 6.5 Hz, IH, CH pyridyl); 8.54 (s, IH, CH, pyridyl)
(27): 2-[3-(Aminooxy)propoxy]-5-(trifluormethyl)pyridin(27): 2- [3- (Aminooxy) propoxy] -5- (trifluoromethyl) pyridine
- - - -
2 g l-(3-{[5(Trifluor-methyl)pyridin-2-yl]oxy}propoxy)pyrrolidin-2,5-dion werden in 60 ml Dichlormethan und 3 ml Methanol vorgelegt. Anschließend werden 378 mg Hydrazinhydrat zugegeben. Man lässt ca. 4 h unter Rückfluss Rühren.2 g of 1- (3 - {[5 (trifluoro-methyl) -pyridin-2-yl] oxy} -propoxy) -pyrrolidine-2,5-dione are initially charged in 60 ml of dichloromethane and 3 ml of methanol. Subsequently, 378 mg of hydrazine hydrate are added. It is allowed to stir for about 4 h under reflux.
Nach dem Abkühlen wird gegen 5N Ammoniak-Lösung extrahiert. Die organische Phase wird abtrennt, über Natriumsulfat getrocknet, filtriert und zur Trockene eingeengt. Man erhält 0,77 g 2- [3-(Aminooxy)propoxy]-5-(trifluormethyl)pyridin.After cooling, it is extracted against 5N ammonia solution. The organic phase is separated, dried over sodium sulfate, filtered and concentrated to dryness. This gives 0.77 g of 2- [3- (aminooxy) propoxy] -5- (trifluoromethyl) pyridine.
1H-NMR(CD3CN): 2,02 (dt, 2H, CH2); 3,72 (t, J= 6,3 Hz, 2H, CH2); 4,40 (t, J= 6,6 Hz, 2H, CH2); 6,88 (d, J= 8,8 Hz, IH, CH, Pyridyl); 7,22 (bs, 2H, NH2); 7,90 (dd, J= 8,8 Hz, J= 2,6 Hz, IH, CH, Pyridyl); 8,49 (s, IH, CH, Pyridyl). 1 H-NMR (CD 3 CN): 2.02 (dt, 2H, CH 2 ); 3.72 (t, J = 6.3 Hz, 2H, CH 2 ); 4.40 (t, J = 6.6 Hz, 2H, CH 2 ); 6.88 (d, J = 8.8 Hz, IH, CH, pyridyl); 7.22 (bs, 2H, NH 2 ); 7.90 (dd, J = 8.8 Hz, J = 2.6 Hz, IH, CH, pyridyl); 8.49 (s, IH, CH, pyridyl).
(28): l-[3-Chlor-5-(3,3-dichlor-allyloxy)-2-methoxy-phenyl]-ethanon O-[l-(6-chlor-pyri- din-3-yl)-ethyl] -oxim(28): 1- [3-chloro-5- (3,3-dichloroallyloxy) -2-methoxyphenyl] ethanone O- [1- (6-chloro-pyridin-3-yl) - ethyl] oxime
112 mg O-[l-(6-Chlor-pyridin-3-yl)-ethyl]-hydroxylamin werden zu einer Lösung von l-[3-Chlor- 5-(3,3-dichlor-allyloxy)-2-hydroxy-phenyl]-ethanon in 5 ml abs. Pyridin unter Stickstoff gegeben. Man lässt über Nacht bei 25 0C rühren. Das Reaktionsgemisch wird zur Trockene eingeengt und über Kieselgel mit Cyclohexan: Essigester 4:1 chromatographiert. Man erhält 81 mg des l-[3- Chlor-5-(3,3-dichlor-allyloxy)-2-methoxy-phenyl]-ethanon O-[l-(6-chlor-pyridin-3-yl)-ethyl]- oxims. M+(ES+)=(M+ 463, 75) 1H-NMR(CD3CN): 1 ,58 (d, J= 6,7 Hz, 3H, CH3); 2,22 (s, 3H, CH3); 3,58 (s, 3H, OCH3); 4,61 (d, J= 6,4 Hz, 2H, OCH2CHCCl2); 5,36 (g, J= 6,7 Hz, IH, CH); 6,22 (t, J= 6,4 Hz, OCH2CHCCl2); 6,68 (d, J= 3,1 Hz, IH, CH, Aryl); 7,01 (d, J= 3,1 Hz, IH, CH, Aryl); 7,38 (d, J= 8,3 Hz, IH, Pyridyl); 7,75 (dd, J= 8,3 und 2,4 Hz, IH, Pyridyl); 8,37 (d, J= 2,4 Hz, IH, Pyridyl). - -112 mg of O- [1- (6-chloro-pyridin-3-yl) -ethyl] -hydroxylamine become a solution of 1- [3-chloro-5- (3,3-dichloroallyloxy) -2-hydroxy -phenyl] -ethanone in 5 ml of abs. Pyridine is added under nitrogen. The mixture is stirred at 25 ° C. overnight. The reaction mixture is evaporated to dryness and chromatographed over silica gel with cyclohexane: ethyl acetate 4: 1. This gives 81 mg of 1- [3-chloro-5- (3,3-dichloroallyloxy) -2-methoxyphenyl] ethanone O- [1- (6-chloro-pyridin-3-yl) -ethyl ] - oxime. M + (ES +) = (M + 463, 75) 1 H-NMR (CD 3 CN): 1.58 (d, J = 6.7 Hz, 3H, CH 3 ); 2.22 (s, 3H, CH 3 ); 3.58 (s, 3H, OCH 3 ); 4.61 (d, J = 6.4 Hz, 2H, OCH 2 CHCCl 2 ); 5.36 (g, J = 6.7 Hz, IH, CH); 6.22 (t, J = 6.4 Hz, OCH 2 CHCCl 2 ); 6.68 (d, J = 3.1 Hz, IH, CH, aryl); 7.01 (d, J = 3.1 Hz, IH, CH, aryl); 7.38 (d, J = 8.3 Hz, IH, pyridyl); 7.75 (dd, J = 8.3 and 2.4 Hz, IH, pyridyl); 8.37 (d, J = 2.4 Hz, IH, pyridyl). - -
Analog der Vorschrift zu (35): l-[3-Chlor-5-(3,3-dichlor-aIIyloxy)-2-methoxy-phenyl]- etbanon O-[l-(6-chlor-pyridin-3-yl)-ethyl]-oxim wurden folgende Verbindungen der allgemeinen Formel I synthetisiert:Analogously to the procedure for (35): 1- [3-chloro-5- (3,3-dichloro-alyloxy) -2-methoxyphenyl] -etbanone O- [1- (6-chloro-pyridin-3-yl ) -ethyl] -oxime, the following compounds of general formula I were synthesized:
Tabelle 2a für X = direkte BindungTable 2a for X = direct bond
Physikalischephysical
Name A1 R1 R2 R3 R4 R5 R6 DatenName A 1 R 1 R 2 R 3 R 4 R 5 R 6 Data
(29): CH2CHCCl2 OCH3 Cl H H CH3 nr ^CF3 (29): CH 2 CHCCl 2 OCH 3 Cl HH CH 3 nr ^ CF 3
CH2 (M+ 498, 100)CH 2 (M + 498, 100)
(30): CH2CHCCl2 OCH3 Cl H H CH3 ^Ph CH2 (M+ 524, 100)(30): CH 2 CHCCl 2 OCH 3 Cl HH CH 3 ^ Ph CH 2 (M + 524, 100)
Cyclocyclo
(31): CH2CHCCl2 OCH3 Cl H H 0, 100) propyl ,Ph CH2 (M+ 55(31): CH 2 CHCCl 2 OCH 3 Cl HH 0, 100) propyl, Ph CH 2 (M + 55
(32): CH2CHCCl2 OCH3 Cl H H CH3 CH2 (M+ 483, 68) (32): CH 2 CHCCl 2 OCH 3 Cl HH CH 3 CH 2 (M + 483, 68)
ClCl
(33): CH2CHCCl2 OCH3 Cl H H CH3 CH2 (M+ 449, 84)(33): CH 2 CHCCl 2 OCH 3 Cl HH CH 3 CH 2 (M + 449, 84)
(34): CH2CHCCl2 OCH3 Cl H H CH3 (CH2)2 (M+ 547, 100) -(34): CH 2 CHCCl 2 OCH 3 Cl HH CH 3 (CH 2 ) 2 (M + 547, 100) -
Ph = Phenyl, Me = MethylPh = phenyl, Me = methyl
Analog der Vorschrift zu (35): l-[3-Chlor-5-(3,3-dichlor-allyloxy)-2-methoxy-phenyl]- ethanon O-[l-(6-chlor-pyridin-3-yl)-ethyl]-oxim wurden folgende Verbindung der allgemeinen Formel I synthetisiert:Analogously to the procedure for (35): 1- [3-chloro-5- (3,3-dichloroallyloxy) -2-methoxyphenyl] ethanone O- [1- (6-chloropyridin-3-yl ) -ethyl] oxime, the following compound of general formula I were synthesized:
Tabelle 2b für X= O BindungTable 2b for X = O bond
(50): N-{4-[2-({[(lE)-{3-chlor-5-[(3,3-dichlorprop-2-en-l-yl)oxy]-2- methoxyphenyl}(cyclopropyl)methylene] amino}oxy)ethyl] phenyI}-2- methylpropanamid (50): N- {4- [2 - ({[(LE) - {3-chloro-5 - [(3,3-dichloroprop-2-en-1-yl) oxy] -2-methoxyphenyl} ( cyclopropyl) methylene] amino} oxy) ethyl] phenyl] -2-methylpropanamide
132 mg N-{4-[2-(Aminooxy)ethyl]phenyl}-2-methylpropanamid werden zu einer Lösung von 100 mg [3-Chlor-5-(3,3-dichlor-allyloxy)-2-methoxy-phenyl]-cyclopropyl-methanon in 5 ml abs. Pyri- din und 5 ml Toluol unter Stickstoff gegeben. Man lässt über Nacht am Wasserabscheider unter Rückfluss rühren. Das Reaktionsgemisch wird zu Trockene eingeengt. Anschließend werden erneut 5 ml Pyridin und Toluol zugegeben. Man lässt wieder über Nacht am Wasserabscheider unter Rückfluss rühren.132 mg of N- {4- [2- (aminooxy) ethyl] phenyl} -2-methylpropanamide are added to a solution of 100 mg of [3-chloro-5- (3,3-dichloroallyloxy) -2-methoxy-phenyl ] -cyclopropyl-methanone in 5 ml abs. Pyridine and 5 ml of toluene under nitrogen. It is allowed to stir overnight at the water separator under reflux. The reaction mixture is concentrated to dryness. Subsequently, 5 ml of pyridine and toluene are added again. It is again stirred overnight at the water separator under reflux.
Das Reaktionsgemisch wird zur Trockene eingeengt, und der Rückstand durch Flashchromatographie gereinigt (Cyclohexan:Essigester 4:1). Man erhält 44,5 mg des N-{4-[2-({[(lE)-{3-chlor- 5-[(3,3-dichlorprop-2-en-l -yl)oxy]-2 methoxyphenyl} (cyclopropyl)methylene]amino} oxy)ethyl]- phenyl}-2-methylpropanamid als E/Z-Isomerengemisch. M+(ES+)= (539, 100)The reaction mixture is concentrated to dryness and the residue is purified by flash chromatography (cyclohexane: ethyl acetate 4: 1). This gives 44.5 mg of N- {4- [2- ({[(LE) - {3-chloro-5 - [(3,3-dichloroprop-2-en-1-yl) oxy] -2-methoxyphenyl } (cyclopropyl) methylene] amino} oxy) ethyl] phenyl} -2-methylpropanamide as E / Z isomer mixture. M + (ES +) = (539, 100)
1H-NMR(CD3CN): 0,41-0,43 (m, 2H, CH2, cPr); 0,64-0,69 (m, 2H, CH2, cPr); 0,77-0,84 (m, 4H, CH2, cPr); 1,71-1,80 (m, IH, CH, cPr); 2,31-2,38 (m, IH, CH); 2,50-2,52 (m, IH, CH); 2,80 (t, J= 6,6 Hz, 2H, CH2); 2,95 (t, J= 6,7 Hz, 2H, CH2); 3,62 (s, 3H, OCH3); 3,76 (s, 3H, OCH3); 4,11 (t, J= 6,6 Hz, 2H, CH2); 4,28 (t, J= 6,7 Hz, 2H, CH2); 4,59 (d, J= 6,5 Hz, 2H, OCH2CHCCl2); 4,64 (d, J= 6,4 Hz, 2H, OCH2CHCCl2); 1 H-NMR (CD 3 CN): 0.41-0.43 (m, 2H, CH 2 , cPr); 0.64-0.69 (m, 2H, CH 2 , cPr); 0.77-0.84 (m, 4H, CH 2 , cPr); 1.71-1.80 (m, IH, CH, cPr); 2.31-2.38 (m, IH, CH); 2.50-2.52 (m, IH, CH); 2.80 (t, J = 6.6 Hz, 2H, CH 2 ); 2.95 (t, J = 6.7 Hz, 2H, CH 2 ); 3.62 (s, 3H, OCH 3 ); 3.76 (s, 3H, OCH 3 ); 4.11 (t, J = 6.6 Hz, 2H, CH 2 ); 4.28 (t, J = 6.7 Hz, 2H, CH 2 ); 4.59 (d, J = 6.5 Hz, 2H, OCH 2 CHCCl 2 ); 4.64 (d, J = 6.4 Hz, 2H, OCH 2 CHCCl 2 );
6,22-6,25 (m, 2xlH, OCH2CHCCl); 6,44 (d, J= 3,0 Hz, IH, Aryl); 6,58 (d, J= 3,0 Hz, IH, Aryl); 6,99-7,04 (m, H, Aryl); 7,21 (d, J= 8,5 Hz, IH, Aryl); 7,40 (d, J= 8,5 Hz, IH, Aryl); 7,49 (d, J= 8,5 Hz, IH, Aryl); 8,1-8,2 (bd, 2H, NH). - -6.22-6.25 (m, 2xlH, OCH 2 CHCCl); 6.44 (d, J = 3.0 Hz, IH, aryl); 6.58 (d, J = 3.0 Hz, IH, aryl); 6.99-7.04 (m, H, aryl); 7.21 (d, J = 8.5 Hz, IH, aryl); 7.40 (d, J = 8.5 Hz, IH, aryl); 7.49 (d, J = 8.5 Hz, IH, aryl); 8.1-8.2 (bd, 2H, NH). - -
Analog der Vorschrift zu (50): N-{4-[2-({[(lE)-{3-chlor-5-[(3,3-dichlorprop-2-en-l-yl)oxy]-2- methoxyphenyl}(cyclopropyl)methylen] amino}oxy)ethyl]phenyl}-2-methyIpropanamid wurden folgende Verbindungen der allgemeinen Formel I synthetisiert:Analogous to the procedure for (50): N- {4- [2 - ({[(LE) - {3-chloro-5 - [(3,3-dichloroprop-2-en-1-yl) oxy] -2 - methoxyphenyl} (cyclopropyl) methylene] amino} oxy) ethyl] phenyl} -2-methylpropanamide the following compounds of general formula I were synthesized:
Tabelle 3a für X= direkte BindungTable 3a for X = direct bond
- - - -
Analog der Vorschrift zu (50): N-{4-[2-({[(lE)-{3-chlor-5-[(3,3-dichlorprop-2-en-l-yl)oxy]-2- methoxyphenyl}(cyclopropyl)methylen] amino}oxy)ethyl]phenyl}-2-methylpropanamid wurde folgende Verbindung der allgemeinen Formel I synthetisiert:Analogous to the procedure for (50): N- {4- [2 - ({[(LE) - {3-chloro-5 - [(3,3-dichloroprop-2-en-1-yl) oxy] -2 - methoxyphenyl} (cyclopropyl) methylene] amino} oxy) ethyl] phenyl} -2-methylpropanamide, the following compound of general formula I was synthesized:
Tabelle 3b für X= O BindungTable 3b for X = O bond
(63): 4-{l-(3-Chlor-5-(3,3-dichlor-allyloxy)-2-methoxy-phenyl]-ethylideneaminooxy}- buttersäure (63): 4- {1- (3-Chloro-5- (3,3-dichloro-allyloxy) -2-methoxy-phenyl] -ethylideneaminooxy} -butyric acid
1,2 g l-[3-Chlor-5-(3,3-dichlor-allyloxy)-2-hydroxy-phenyl]-ethanon werden zusammen mit 664 mg 4-Aminooxy-buttersäurehydrochlorid in Gegenwart von Molsieb in 60 ml abs. Methanol bei RT für 3 Tage gerührt. Das Reaktionsgemisch wird filtriert, zur Trockene eingeengt, der Rückstand wird mit Ethylacetat verdünnt und mit Wasser gewaschen, über Natriumsulfat getrocknet, filtriert und zur Trockene aufkonzentriert.1.2 g of 1- [3-chloro-5- (3,3-dichloroallyloxy) -2-hydroxyphenyl] -ethanone are together with 664 mg of 4-aminooxy-butyric acid hydrochloride in the presence of molecular sieve in 60 ml of abs. Methanol stirred at RT for 3 days. The reaction mixture is filtered, concentrated to dryness, the residue is diluted with ethyl acetate and washed with water, dried over sodium sulfate, filtered and concentrated to dryness.
Der Rückstand wird in Methanol aufgenommen, mit 2 ml Wasser und 1 g Kaliumcarbonat versetzt und über Nacht bei RT gerührt. Das Reaktionsgemisch wird zur Trockene eingeengt, in Wasser/EE 1:1 aufgenommen, und einmal mit Ethylacetat extrahiert. Die wässrige Phase wird mit IN-HCl angesäuert und mehrfach mit Ethylacetat extrahiert. Die vereinten organischen Phasen werden über Natriumsulfat getrocknet, filtriert und zur Trockene eingeengt. Man erhält 354 mg der 4-{l- [S-Chlor-S-CSjS-dichlor-allyloxyJ^-methoxy-pheny^-ethylidenaminooxyJ-buttersäure. M+(ES+)= (408, 98) 1H-NMR(CD3CN): 2,08-2,26 (m, 2H, CH2 und Wasser); 2,16 (s, 3H, CH3); 2,40 (t, J= 7,3 Hz, 2H, CH2); 3,72 (s, 3H, CH3); 4,16 (t, J= 6,3 Hz, 2H, CH2); 4,65 (d, J= 6,4 Hz, 2H, OCH2CHCCl2); 6,26 (t, J= 6,4 Hz, IH, OCH2CHCCl2); 6,81 (d, J= 3,1 Hz, CH, Aryl); 7,04 (d, (d, J= 3,1 Hz, CH, Aryl)The residue is taken up in methanol, treated with 2 ml of water and 1 g of potassium carbonate and stirred overnight at RT. The reaction mixture is concentrated to dryness, taken up in water / EA 1: 1 and extracted once with ethyl acetate. The aqueous phase is acidified with IN HCl and extracted several times with ethyl acetate. The combined organic phases are dried over sodium sulfate, filtered and concentrated to dryness. This gives 354 mg of 4- {l- [S-chloro-S-CS j S-dichloro-allyloxyJ ^ -methoxy-pheny ^ -ethylidenaminooxyJ-butyric acid. M + (ES +) = (408, 98) 1 H-NMR (CD 3 CN): 2.08-2.26 (m, 2H, CH 2 and water); 2.16 (s, 3H, CH 3); 2.40 (t, J = 7.3 Hz, 2H, CH 2 ); 3.72 (s, 3H, CH 3); 4.16 (t, J = 6.3 Hz, 2H, CH 2 ); 4.65 (d, J = 6.4 Hz, 2H, OCH 2 CHCCl 2 ); 6.26 (t, J = 6.4 Hz, IH, OCH 2 CHCCl 2 ); 6.81 (d, J = 3.1 Hz, CH, aryl); 7.04 (d, (d, J = 3.1 Hz, CH, aryl)
(64): 4-{l-[3-Chlor-5-(3,3-dichlor-allyloxy)-2-methoxy-phenyl]-ethylidenaminooxy}-N- phenyl-butyramid(64): 4- {1- [3-Chloro-5- (3,3-dichloroallyloxy) -2-methoxyphenyl] ethylideneaminooxy} -N-phenylbutyramide
50 mg 4- { 1 -[3-Chlor-5-(3,3-dichlor-allyloxy)-2-methoxy-phenyl]-ethyliden-aminooxy} -buttersäure werden in 2 ml Dichlormethan vorgelegt mit 13 mg Anilin, 7,5 mg DMAP und 37 mg Triethylamin - -50 mg of 4- {1 - [3-chloro-5- (3,3-dichloroallyloxy) -2-methoxyphenyl] ethylidene-aminooxy} -butyric acid are initially introduced in 2 ml of dichloromethane with 13 mg of aniline, 7, 5 mg DMAP and 37 mg triethylamine - -
versetzt. Anschließend werden 28 mg N-(3-Dimethylaminopropyl)-N-ethylcarbodiimid hydro- chlorid gelöst in 1 ml Dichlormethan zugetropft und über Nacht bei RT gerührt. Das Reaktionsgemisch wird mit IN HCl gewaschen, die organische Phase über Natriumsulfat getrocknet, filtriert und zur Trockene eingeengt. Das Rohprodukt wird durch Flashchromatographie gereinigt (Eluent: Dichlormethan/Methanol 98:2). Man erhält 18 mg des 4-{l-[3-Chlor-5-(3,3-dichlor-allyloxy)-2- methoxy-phenyl]-ethylidenaminooxy}-N-phenyl-butyramids. (M+ 485, 100)added. Then 28 mg of N- (3-dimethylaminopropyl) -N-ethylcarbodiimide hydrochloride dissolved in 1 ml of dichloromethane are added dropwise and the mixture is stirred at RT overnight. The reaction mixture is washed with IN HCl, the organic phase dried over sodium sulfate, filtered and concentrated to dryness. The crude product is purified by flash chromatography (eluent: dichloromethane / methanol 98: 2). This gives 18 mg of 4- {1- [3-chloro-5- (3,3-dichloroallyloxy) -2-methoxyphenyl] ethylideneaminooxy} -N-phenylbutyramide. (M + 485, 100)
1H-NMR(CD3CN): 2,04 (t, J= 7,2 Hz, CH2); 2,15 (s, 33,71H, CH3); 2,44 (t, J= 7,3 Hz, 2H, CH2); 3,71 (s, 3H, OCH3); 4,21 (t, J= 6,3 Hz, 2H, CH2); 4,64 (d, J= 6,4 Hz, 2H, OCH2CHCCl2); 6,25 (t, J=6,4 Hz, IH, OCH2CHCCl2); 6,82 (d, J= 3,1 Hz, IH, Aryl); 7,04 (d, J= 3,1 Hz, IH, Aryl); 7,04- 7,08 (m, IH, Anilin); 7,29 (dd, 2H, J= 5,8 und 6,6 Hz, Anilin); 7,55 (d, 2H; J= 7,6 Hz); 8,3 (bs, IH, NH). 1 H-NMR (CD 3 CN): 2.04 (t, J = 7.2 Hz, CH 2 ); 2.15 (s, 33,71H, CH 3); 2.44 (t, J = 7.3 Hz, 2H, CH 2 ); 3.71 (s, 3H, OCH 3 ); 4.21 (t, J = 6.3 Hz, 2H, CH 2 ); 4.64 (d, J = 6.4 Hz, 2H, OCH 2 CHCCl 2 ); 6.25 (t, J = 6.4 Hz, IH, OCH 2 CHCCl 2 ); 6.82 (d, J = 3.1 Hz, IH, aryl); 7.04 (d, J = 3.1 Hz, IH, aryl); 7.04-7.08 (m, IH, aniline); 7.29 (dd, 2H, J = 5.8 and 6.6 Hz, aniline); 7.55 (d, 2H, J = 7.6 Hz); 8.3 (bs, IH, NH).
Analog zu (64): wurde (65) synthetisiert:Analogous to (64): (65) was synthesized:
(66): Ethyl (2E)-3-{4-[(4-{[((lE)-l-{3-chlor-5-[(3,3-dichlorprop-2-en-l-yl)oxy]-2-methoxy- phenyl} ethylidene)amino] oxy} butanoyl)amino] phenyl} acrylat(66): Ethyl (2E) -3- {4 - [(4 - {[((IE) -l- {3-chloro-5 - [(3,3-dichloro-prop-2-en-1-yl) oxy] -2-methoxyphenyl} ethylidene) amino] oxy} butanoyl) amino] phenyl} acrylate
50 mg 4-{l-[3-Chlor-5-(3,3-dichlor-allyloxy)-2-methoxy-phenyl]-ethyliden-aminooxy} buttersäure werden in 2 ml Dichlormethan vorgelegt und mit 17 mg Oxalylchlorid und einem Tropfen DMF versetzt. Nach beendeter Gasentwicklung werden 25 mg Ethyl (2E)-3-(4-aminophenyl)acrylat als Lösung in 1 ml Dichlormethan zusammen mit 37 mg Triethylamin zugetropft. Man läßt über Nacht bei Raum Temperatur rühren. -50 mg of 4- {1- [3-chloro-5- (3,3-dichloroallyloxy) -2-methoxyphenyl] ethylidene-aminooxy} butyric acid are introduced into 2 ml of dichloromethane and admixed with 17 mg of oxalyl chloride and one drop DMF offset. After completion of the evolution of gas, 25 mg of ethyl (2E) -3- (4-aminophenyl) acrylate are added dropwise as a solution in 1 ml of dichloromethane together with 37 mg of triethylamine. It is allowed to stir overnight at room temperature. -
Das Reaktionsgemisch wird mit IN HCl gewaschen, die organische Phase über Natriumsulfat getrocknet, filtriert und zur Trockene eingeengt. Das Rohprodukt wird durch Flashchromatographie gereinigt (Eluent: Dichlormethan/Methanol 98:2). Man erhält 11 mg Ethyl (2E)-3-{4-[(4- {[((lE)-l-{3-chlor-5-[(3,3-dichloφrop-2-en-l-yl)oxy]-2-methoxyphenyl}ethylidene)amino]oxy}- butanoyl)amino]phenyl} acrylat.The reaction mixture is washed with IN HCl, the organic phase dried over sodium sulfate, filtered and concentrated to dryness. The crude product is purified by flash chromatography (eluent: dichloromethane / methanol 98: 2). This gives 11 mg of ethyl (2E) -3- {4 - [(4- {[((LE) -l- {3-chloro-5 - [(3,3-dichloro-2-en-l-yl) oxy] -2-methoxyphenyl} ethylidenes) amino] oxy} -butanoyl) amino] phenyl} acrylate.
1H-NMR: 1,33 (t, J= 7,1 Hz, 3H, CH3 Ethyl); 2,16 (t, J= 6,5 Hz, 2H, CH2); 2,22 (s, 3H, CH3); 2,54 (t, J= 6,9 Hz, 2H, CH2); 3,76 (s, 3H, OCH3); 4,27-4,30 (m, 4H, 2x CH2); 4,59 (d, J= 6,3 Hz, 2H, OCH2CHCCl2); 6,10 (t, J= 6,3 Hz, IH, OCH2CHCCl2); 6,35 (d, J= 16 Hz, IH, CH=CH); 6,75 (d, J= 3,0 Hz, IH, Aryl); 6,95 (d, J= 3,0 Hz, IH, Aryl); 7,44-7,51 (m, 4H, Aryl); 7,62 (d, J= 16 Hz, IH, CH); 7,76 (bs, IH, NH). 1 H-NMR: 1.33 (t, J = 7.1 Hz, 3H, CH 3 ethyl); 2.16 (t, J = 6.5 Hz, 2H, CH 2 ); 2.22 (s, 3H, CH 3 ); 2.54 (t, J = 6.9 Hz, 2H, CH 2 ); 3.76 (s, 3H, OCH 3 ); 4.27-4.30 (m, 4H, 2x CH 2 ); 4.59 (d, J = 6.3 Hz, 2H, OCH 2 CHCCl 2 ); 6.10 (t, J = 6.3 Hz, IH, OCH 2 CHCCl 2 ); 6.35 (d, J = 16 Hz, IH, CH = CH); 6.75 (d, J = 3.0 Hz, IH, aryl); 6.95 (d, J = 3.0 Hz, IH, aryl); 7.44-7.51 (m, 4H, aryl); 7.62 (d, J = 16 Hz, IH, CH); 7.76 (bs, IH, NH).
Analog der Vorschrift zu (66): Ethyl (2E)-3-{4-[(4-{[((lE)-l-{3-chlor-5-[(3,3-dichlorprop-2- en-l-yl)oxy]-2-methoxyphenyl}ethyliden)amino]oxy} butanoyl)amino]phenyl}acrylat wurden folgende Verbindungen der allgemeinen Formel I synthetisiert:Analogously to the procedure for (66): ethyl (2E) -3- {4 - [(4 - {[((IE) -l- {3-chloro-5 - [(3,3-dichloroprop-2-ene] 1-yl) oxy] -2-methoxyphenyl} ethylidene) amino] oxy} butanoyl) amino] phenyl} acrylate, the following compounds of general formula I were synthesized:
Tabelle 4 für X= NHTable 4 for X = NH
- - - -
(69): 2,2-Dimethyl-2,3-dihydro-l-benzofuran-7-yl 4-{[((lE)-l-{3-chlor-5-[(3,3-dichlorprop- 2-en-l-yl)oxy]-2-methoxyphenyI}ethyliden)amino]oxy} butyrat(69): 2,2-Dimethyl-2,3-dihydro-1-benzofuran-7-yl 4 - {[((IE) -l- {3-chloro-5 - [(3,3-dichloroprop-2 -en-1-yl) oxy] -2-methoxyphenyl} ethylidene) amino] oxy} butyrate
50 mg 4- { 1 -[3-Chlor-5-(3,3-dichlor-allyloxy)-2-methoxy-phenyl]-ethyliden-amino-oxy} -buttersäure werden in 2 ml Dichlormethan vorgelegt und nacheinander mit 22 mg 2,2-Dimethyl-2,3- dihydro-l-benzofuran-7-ol, 7,5 mg 4-Dimethylaminopyridin und 40 mg Triethylamin versetzt. Anschließend werden 28 mg 1,3-Dicyclohexylcarbodiimid als Lösung in 1 ml Dichlormethan zugetropft und über Nacht bei RT gerührt. Anschließend wird Ih unter Rückfluss gerührt.50 mg of 4- {1 - [3-chloro-5- (3,3-dichloroallyloxy) -2-methoxyphenyl] ethylidene-amino-oxy} -butyric acid are initially charged in 2 ml of dichloromethane and admixed successively with 22 mg Added 2,2-dimethyl-2,3-dihydro-l-benzofuran-7-ol, 7.5 mg of 4-dimethylaminopyridine and 40 mg of triethylamine. Subsequently, 28 mg of 1,3-dicyclohexylcarbodiimide are added dropwise as a solution in 1 ml of dichloromethane and stirred overnight at RT. Then Ih is stirred under reflux.
Das Reaktionsgemisch wird mit IN HCl gewaschen, die organische Phase über Natriumsulfat getrocknet, filtriert und zur Trockene eingeengt. Nach Reinigung mittels HPLC erhält man 27 mg von 2,2-Dimethyl-2,3-dihydro- 1 -benzofuran-7-yl 4- { [(( 1 E)- 1 - {3-chlor-5-[(3 ,3-dichlorprop-2-en-l - yl)oxy]-2-methoxyphenyl}ethyliden)amino]oxy} butanoat als E/Z-Isomerengemisch. M+(ES+)= (556, 100)The reaction mixture is washed with IN HCl, the organic phase dried over sodium sulfate, filtered and concentrated to dryness. After purification by HPLC, 27 mg of 2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl 4- {[((1 E) -1 - {3-chloro-5 - [(3 , 3-dichloroprop-2-en-1-yl) oxy] -2-methoxyphenyl} ethylidene) amino] oxy} butanoate as E / Z isomer mixture. M + (ES +) = (556, 100)
1H-NMR(CD3CN): 2,06-2,12 (m, 4H, 2xCH2); 2,14 (s, 12H, 4xCH3); 2,15 (s, 3H, CH3); 2,18 (s, 3H, CH3); 4,15 (t, J= 6,3 Hz, 2H, CH2); 4,25 (t, J= 6,3 Hz, 2H, CH2); 4,64-4,66 (m, 4H, 2x OCH2CHCCl2); 6,23-6,26 (m, 2H, 2xOCH2CHCCl2); 6,81-6,84 (m, 6H, Aryl); 7,04-7,05 (m, 4H, Aryl). 1 H-NMR (CD 3 CN): 2.06-2.12 (m, 4H, 2xCH 2 ); 2.14 (s, 12H, 4xCH 3); 2.15 (s, 3H, CH 3); 2.18 (s, 3H, CH 3); 4.15 (t, J = 6.3 Hz, 2H, CH 2 ); 4.25 (t, J = 6.3 Hz, 2H, CH 2 ); 4.64-4.66 (m, 4H, 2x OCH 2 CHCCl 2 ); 6.23-6.26 (m, 2H, 2xOCH 2 CHCCl 2 ); 6.81-6.84 (m, 6H, aryl); 7.04-7.05 (m, 4H, aryl).
(70): (2-Hydroxy-5-methoxy-phenyl)-cyclopropylketon (A) (2,5-Dimethoxyphenyl)-cyclopropyIketon (B)(70): (2-Hydroxy-5-methoxyphenyl) cyclopropyl ketone (A) (2,5-dimethoxyphenyl) cyclopropyl ketone (B)
Unter Schutzgas werden 48.2g AlCl3 in 350 mL 1,2-Dichlorethan vorgelegt und mit 50g 1,4- Dimethoxybenzol versetzt. Anschließend werden 37.8g Cyclopropylcarbonsäurechlorid langsam zugetropft und das Gemisch mehrere Stunden unter Rückfluss gerührt. Das Gemisch wird nach dem Abkühlen auf Eiswasser ausgetragen, mit wenig konz. HCl versetzt und die wässrige Phase . .Under protective gas, 48.2 g of AlCl 3 in 350 mL of 1,2-dichloroethane are introduced and mixed with 50 g of 1,4-dimethoxybenzene. Subsequently, 37.8 g of cyclopropylcarboxylic acid are slowly added dropwise and the mixture is stirred under reflux for several hours. The mixture is discharged after cooling on ice water, with little conc. HCl and the aqueous phase , ,
zweimal mit Dichlormethan extrahiert. Die vereinigten organischen Phasen werden getrocknet und konzentriert. Man erhält 50g eines 2:1 -Gemisches aus (2-Hydroxy-5-methoxy-phenyl)-cyclo- propylketon (A) und (2,5-Dimethoxyphenyl)-cyclopropylketon (B) als gelben Feststoff, welcher im nächsten Schritt eingesetzt wird. M+(ES+)= (193, 100) für A; (207, 100) für Bextracted twice with dichloromethane. The combined organic phases are dried and concentrated. This gives 50 g of a 2: 1 mixture of (2-hydroxy-5-methoxyphenyl) cyclopropyl ketone (A) and (2,5-dimethoxyphenyl) cyclopropyl ketone (B) as a yellow solid, which is used in the next step becomes. M + (ES +) = (193, 100) for A; (207, 100) for B
1H-NMR(DMSO-Do) für A: 1.11 (m, 4H, -cPr); 3.04 (m, IH, -cPr); 3.78 (s, 3H, -OMe); 6.92 (d, J=9 Hz, IH, Aryl); 7.17 (dd, J=2.1 Hz, 9 Hz, IH, Aryl); 7.53 (d, J=3.1 Hz, IH, Aryl); 11.58 (s, IH, OH) 1 H-NMR (DMSO-Do) for A: 1.11 (m, 4H, -cPr); 3.04 (m, IH, -cPr); 3.78 (s, 3H, -OMe); 6.92 (d, J = 9 Hz, IH, aryl); 7.17 (dd, J = 2.1 Hz, 9 Hz, IH, aryl); 7.53 (d, J = 3.1 Hz, IH, aryl); 11.58 (s, IH, OH)
1H-NMR(DMSO-DO) für B: 1.00 (m, 4H, -cPr); 2.71 (m, IH, -cPr); 3.73 (s, 3H, -OMe); 3.83 (s, 3H, -OMe); 6.97 (m, IH, Aryl); 7.12 (m, 2H, Aryl); 11.20 (s, IH, OH) 1 H-NMR (DMSO-DO) for B: 1.00 (m, 4H, -cPr); 2.71 (m, IH, -cPr); 3.73 (s, 3H, -OMe); 3.83 (s, 3H, -OMe); 6.97 (m, IH, aryl); 7.12 (m, 2H, aryl); 11.20 (s, IH, OH)
(71) (3-Chlor-2-hydroxy-5-methoxy-phenyl)-cyclopropylketon-(2,5-Dimethoxyphenyl)- cyclopropylketon(71) (3-Chloro-2-hydroxy-5-methoxy-phenyl) -cyclopropyl ketone (2,5-dimethoxyphenyl) -cyclopropyl ketone
Eine Lösung von 68g eines ca. 2:1 -Gemisches aus l-(2-Hydroxy-5-methoxyphenyl)-cyclopro- pylketon und (2,5-Dimethoxyphenyl)-cyclopropylketon in DMF wird unter Schutzgas innerhalb von Ih portionsweise mit 57.2g N-Chlorsuccinimid versetzt. Die Reaktionslösung verfärbte sich braun und wird über Nacht bei RT gerührt. Das Reaktionsgemisch wird auf 600 mL Wasser gegossen; dabei fallen 53g (3-Chlor-2-hydroxy-5-methoxy-phenyl)-cyclopropylketon als beigefarbener Feststoff an. Die überstehende wässrige Lösung wird mehrfach mit Dichlormethan extrahiert, die vereinigten organischen Phasen werden mehrfach mit Wasser gewaschen, über Na2SO4 getrocknet, filtriert und zur Trockne eingeengt. Es wurden 35g 2,5-Dimethoxyphenyl)- cyclopropylketon als rötliches Öl erhalten. Beide Verbindungen wurden ohne Aufreinigung im nächsten Schritt eingesetzt. M+(ES+)= (227, 100) 1H-NMR(DMSO-D6): 1.17 (m, 4H, -cPr); 3.07 (m, IH, -cPr); 3.81 (s, 3H, -OMe); 7.42 (d, J=3 Hz, IH, Aryl); 7.66 (d, J=3 Hz, IH, Aryl); 12.25 (s, IH, OH). (72): (3-Chlor-2,5-dihydroxyphenyl)-cycIopropylketonA 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. The supernatant aqueous solution is extracted several times with dichloromethane, the combined organic phases are washed several times with water, dried over Na 2 SO 4 , filtered and concentrated to dryness. There were obtained 35 g of 2,5-dimethoxyphenyl) - cyclopropyl ketone as a reddish oil. Both compounds were used without purification in the next step. M + (ES +) = (227, 100) 1 H-NMR (DMSO-D 6 ): 1.17 (m, 4H, -cPr); 3.07 (m, IH, -cPr); 3.81 (s, 3H, -OMe); 7.42 (d, J = 3 Hz, IH, aryl); 7.66 (d, J = 3 Hz, IH, aryl); 12.25 (s, IH, OH). (72): (3-chloro-2,5-dihydroxyphenyl) cyclopropyl ketone
Unter Schutzgas werden 53g ß-CMor^-hydroxy-S-methoxy-phenyO-cyclopropylketon in 400 mL Dichlormethan vorgelegt und bei 00C tropfenweise mit einer Lösung aus 44.2 mL BBr3 in 100 mL Dichlormethan versetzt. Anschließend wird Ih bei Raumtemperatur nachgerührt und das Gemisch vorsichtig auf Eiswasser gegossen. Nach Phasentrennung wird die wässrige Phase einmal mit Dichlormethan extrahiert, die vereinigten organischen Phasen getrocknet und konzentriert. M+(ES+)= (213, 100)Under protective gas 53 g ß-CMor ^ -hydroxy-S-methoxy-phenyO-cyclopropyl ketone are introduced into 400 mL dichloromethane and treated dropwise at 0 0 C with a solution of 44.2 mL BBr 3 in 100 mL dichloromethane. Then Ih is stirred at room temperature and the mixture poured carefully on ice water. After phase separation, the aqueous phase is extracted once with dichloromethane, the combined organic phases are dried and concentrated. M + (ES +) = (213, 100)
1H-NMR(DMSO-D6): 1.16 (m, 4H, -cPr); 3.13 (m, IH, -cPr); 7.16 (d, J=2.8Hz, IH, Aryl); 7.24 (d, J=2.8Hz, Aryl); 9.5 (s, IH, OH); 11.8 (s, IH, OH) 1 H-NMR (DMSO-D 6 ): 1.16 (m, 4H, -cPr); 3.13 (m, IH, -cPr); 7.16 (d, J = 2.8Hz, IH, aryl); 7.24 (d, J = 2.8Hz, aryl); 9.5 (s, IH, OH); 11.8 (s, IH, OH)
(73): (2,5-Dihydroxyphenyl)-cyclopropylketon(73): (2,5-Dihydroxyphenyl) cyclopropyl ketone
(74): (3-Chlor-2,5-dihydroxyphenyl)-cyclopropylketon(74): (3-chloro-2,5-dihydroxyphenyl) cyclopropyl ketone
(73): Unter Schutzgas werden 35g (2,5-Dimethoxyphenyl)-cyclopropylketon in 300 mL Dichlormethan vorgelegt und auf 00C gekühlt. Anschließend wird eine Lösung von 32 mL BBr3 in 10OmL Dichlormethan langsam zugetropft. Danach wird Ih bei Raumtemperatur nachgerührt und das Gemisch vorsichtig auf Eiswasser gegossen. Nach Phasentrennung wird die wässrige Phase einmal mit Dichlormethan extrahiert, die vereinigten organischen Phasen getrocknet und konzentriert. Man erhält 34g (2,5-Dihydroxyphenyl)-cyclopropylketon in Form eines rötlichen Öls, welches ohne weitere Aufreinigung im nächsten Schritt eingesetzt wird. M+(ES+)= (195, 100)(73): Under protective gas, are introduced 35 g of (2,5-dimethoxyphenyl) -cyclopropylketon in 300 mL of dichloromethane and cooled to 0 0 C. Then a solution of 32 mL BBr 3 in 10OmL dichloromethane is slowly added dropwise. Thereafter, Ih is stirred at room temperature and the mixture is poured carefully onto ice water. After phase separation, the aqueous phase is extracted once with dichloromethane, the combined organic phases are dried and concentrated. This gives 34g (2,5-dihydroxyphenyl) cyclopropyl ketone in the form of a reddish oil, which is used without further purification in the next step. M + (ES +) = (195, 100)
(74): Über einen Zeitraum von 1 h werden 33,1 g N-Chlorsuccinimid unter Stickstoff portionsweise zu einer Lösung von 34 g (2,5-Dihydroxyphenyl)-cyclopropylketon in 400 ml DMF gegeben. Die Reaktionslösung verfärbte sich braun und wird über Nacht bei RT gerührt. Das Reaktionsgemisch wird in 0,5 L Wasser gegossen und mehrfach mit Dichlormethan extrahiert. Die vereinten organischen Phasen werden mehrfach mit Wasser gewaschen, über Na2SO4 getrocknet, filtriert und zur Trockne eingeengt. Es wurden 39g Produkt (75%ig laut LC-MS) als Feststoff erhalten, welches ohne Aufreinigung im nächsten Schritt eingesetzt wurde.(74): Over a period of 1 h, 33.1 g of N-chlorosuccinimide are added in portions under nitrogen to a solution of 34 g (2,5-dihydroxyphenyl) cyclopropyl ketone in 400 ml of DMF. The reaction solution turned brown and is stirred at RT overnight. The The reaction mixture is poured into 0.5 L of water and extracted several times with dichloromethane. The combined organic phases are washed several times with water, dried over Na 2 SO 4 , filtered and concentrated to dryness. There were obtained 39g product (75% by LC-MS) as a solid, which was used without purification in the next step.
(75): (2-Hydroxy-5-methoxyphenyl)-2-methylpropan-l-on(75): (2-hydroxy-5-methoxyphenyl) -2-methylpropan-1-one
Bei Raumtemperatur werden 48,2g AICI3 und 50g 1 ,4-Dimethoxybenzol in 350 mL 1,2- Dichlorethan vorgelegt und langsam 37,9 mL Isobutyrylchlorid zugetropft. Anschließend rührt man 16h unter Rückfluss. Zur Aufarbeitung lässt man abkühlen gießt das Reaktionsgemisch vorsichtig unter Rühren auf 500 mL Eis und lässt 10 min. nachrühren. Anschließend werden die Phasen getrennt und die wässrige Phase 2x mit Dichlormethan extrahiert. Vereinigte organische Phasen werden über Natriumsulfat getrocknet und zur Trockene eingeengt. Es wurden 77g leicht verunreinigtes Produkt (92%ig laut LC-MS) als orangefarbenes Öl erhalten, welches ohne Aufreinigung im nächsten Schritt eingesetzt wurde. M+(ES+)= (195, 100)At room temperature, 48.2 g of AICI 3 and 50 g of 1, 4-dimethoxybenzene are initially charged in 350 mL of 1,2-dichloroethane and slowly added dropwise 37.9 mL of isobutyryl chloride. Then it is stirred for 16 h under reflux. For workup, allowed to cool, the reaction mixture is poured carefully with stirring on 500 mL of ice and allowed 10 min. stirred. The phases are then separated and the aqueous phase extracted 2x with dichloromethane. Combined organic phases are dried over sodium sulfate and concentrated to dryness. There was obtained 77g slightly contaminated product (92% by LC-MS) as an orange oil, which was used without purification in the next step. M + (ES +) = (195, 100)
1H-NMR(DMSO-D6): 1.13 (d, J=6.8Hz, 6H, iPr); 3.74 (m, IH, iPr); 3.75 (s, 3H, OMe); 6.90 (d, J=9Hz, IH, Aryl); 7.14 (dd, J=3.1Hz, 9Hz, Aryl); 7.30 (d, J=3.1Hz, IH, Aryl); 11.4 (s, IH, OH) 1 H-NMR (DMSO-D 6 ): 1.13 (d, J = 6.8Hz, 6H, iPr); 3.74 (m, IH, iPr); 3.75 (s, 3H, OMe); 6.90 (d, J = 9Hz, IH, aryl); 7.14 (dd, J = 3.1Hz, 9Hz, aryl); 7.30 (d, J = 3.1Hz, IH, aryl); 11.4 (s, IH, OH)
(76): (3-Chlor-2-hydroxy-5-methoxyphenyl)-2-methylpropan-l-on(76): (3-chloro-2-hydroxy-5-methoxyphenyl) -2-methylpropan-1-one
Innerhalb von 1 h werden 53,6 g N-Chlorsuccinimid unter Stickstoff portionsweise zu einer Lösung von 60 g (2-Hydroxy-5-methoxyphenyl)-2-methylpropan-l-on in 600 ml DMF gegeben. Die Reaktionslösung verfärbte sich braun und wird über Nacht bei RT gerührt. Das Reaktionsgemisch wird in 1 ,2 1 Wasser gegossen und mehrfach mit Dichlormethan extrahiert. Die vereinten organischen Phasen werden mehrfach mit Wasser gewaschen, über Na2SO4 getrocknet, filtriert und zur Trockne eingeengt. Es wurden 70g Produkt (75%ig laut LC-MS) als Feststoff erhalten, welches ohne Aufreinigung im nächsten Schritt eingesetzt wurde. M+(ES+)= (229, 100)Within 1 h, 53.6 g of N-chlorosuccinimide are added in portions under nitrogen to a solution of 60 g of (2-hydroxy-5-methoxyphenyl) -2-methylpropan-1-one in 600 ml of DMF. The reaction solution turned brown and is stirred at RT overnight. The reaction mixture is poured into 1, 2 1 of water and extracted several times with dichloromethane. The combined organic phases are washed several times with water, dried over Na 2 SO 4 , filtered and concentrated to dryness. There were obtained 70g product (75% by LC-MS) as a solid, which was used without purification in the next step. M + (ES +) = (229, 100)
1H-NMR(DMSO-D6): 1.15 (d, J=6.8Hz, 6H, iPr); 3.79 (m, IH, iPr); 3.79 (s, 3H, OMe); 7.40 (s, 1 H-NMR (DMSO-D 6 ): 1.15 (d, J = 6.8Hz, 6H, iPr); 3.79 (m, IH, iPr); 3.79 (s, 3H, OMe); 7.40 (s,
2H, Aryl); 12,0 (s, IH, OH)2H, aryl); 12.0 (s, IH, OH)
(77): (3-Chlor-2,5-dihvdroxyphenyl)-2-methylpropan-l-on(77): (3-chloro-2,5-dihydroxy-phenyl) -2-methylpropan-1-one
Unter Schutzgas werden 36g (3-Chlor-2-hydroxy-5-Methoxyphenyl)-2-methylpropan-l-on in 36OmL Dichlormethan vorgelegt, auf 00C gekühlt und tropfenweise über binnen 10 min. mit einer Lösung von 3OmL BBr3 in 180 mL Dichlormethan versetzt. Nach 2h Nachrühren bei gegebener Temperatur wird die Reaktionsmischung auf 0,7L Eis gegossen, 30 min. nachgerührt und durch Zugabe von 350 mL ges. NaHCO3-LSg. neutralisiert. Nach Phasentrennung wird die wässrige Phase 3x mit 15OmL Dichlormethan extrahiert, die vereinigten organischen Phasen werden getrocknet und zur Trockne eingeengt. Es werden 33g Produkt (75%ig laut LC-MS) als Öl erhalten, welches ohne Aufreinigung im nächsten Schritt eingesetzt wurde. M+(ES+)= (215, 100)Under inert gas, 36 g of (3-chloro-2-hydroxy-5-methoxyphenyl) -2-methylpropan-l-on in 36OmL dichloromethane, cooled to 0 0 C and dropwise over 10 min. with a solution of 3OmL BBr 3 in 180 mL dichloromethane. After 2 h stirring at a given temperature, the reaction mixture is poured onto 0.7 L of ice, 30 min. stirred and by adding 350 mL sat. NaHCO 3 -LSg. neutralized. After phase separation, the aqueous phase is extracted 3 times with 15OmL dichloromethane, the combined organic phases are dried and concentrated to dryness. There are obtained 33g product (75% according to LC-MS) as an oil, which was used without purification in the next step. M + (ES +) = (215, 100)
IH-NMR(DMSO-D6): 1.14 (d, J=6.8Hz, 6H, iPr); 3.62 (m, IH, iPr); 7.16 (d, J=2.8Hz, IH, Aryl); 7.26 (d, J=2.8Hz, Aryl); 9.5 (s, IH, OH); 11.9 (s, IH, OH)IH-NMR (DMSO-D 6 ): 1.14 (d, J = 6.8Hz, 6H, iPr); 3.62 (m, IH, iPr); 7.16 (d, J = 2.8Hz, IH, aryl); 7.26 (d, J = 2.8Hz, aryl); 9.5 (s, IH, OH); 11.9 (s, IH, OH)
(78): (2,5-Dimethoxy-phenyl)-cyclohexylketon (2-Hydroxy-5-methoxy-phenyl)-cyclo- hexylketon(78): (2,5-Dimethoxyphenyl) cyclohexyl ketone (2-hydroxy-5-methoxyphenyl) cyclohexyl ketone
Bei Raumtemperatur werden 48,2g AlCl3 und 50g 1,4-Dimethoxybenzol in 350 mL 1,2- Dichlorethan vorgelegt und langsam 53 g Cyclohexylcarbonylchlorid zugetropft. Anschliessend rührt man 16h unter Rückfluss. Zur Aufarbeitung lässt man abkühlen gießt das Reaktionsgemisch vorsichtig unter Rühren auf 500 mL Eis und läßt 10 min. nachrühren. Anschließend werden die Phasen getrennt und die wässrige Phase 2x mit Dichlormethan extrahiert. Vereinigte organische Phasen werden über Natriumsulfat getrocknet und zur Trockene eingeengt. Als Rohprodukt - -At room temperature, 48.2 g of AlCl 3 and 50 g of 1,4-dimethoxybenzene are initially charged in 350 mL of 1,2-dichloroethane and slowly added dropwise 53 g of cyclohexylcarbonyl chloride. Then it is stirred for 16 h under reflux. For workup, allowed to cool, pour the reaction mixture carefully with stirring to 500 mL of ice and allowed to 10 min. stirred. The phases are then separated and the aqueous phase extracted 2x with dichloromethane. Combined organic phases are dried over sodium sulfate and concentrated to dryness. As a crude product - -
wurden 93g leicht verunreinigtes Produkt (96%ig laut LC-MS) als Gemisch aus (2,5-Dimethoxy- phenyl)-cyclohexylketon (B, 83%) und (2-Hydroxy-5-methoxy-phenyl)-cyclohexylketon (A, 14%) als orangefarbenes Ol erhalten, welches ohne Aufreinigung im nächsten Schritt eingesetzt wurde. M+(ES+)= (235, 100) für B; (221,100) für Awere 93 g slightly contaminated product (96% by LC-MS) as a mixture of (2,5-dimethoxyphenyl) cyclohexyl ketone (B, 83%) and (2-hydroxy-5-methoxyphenyl) cyclohexyl ketone (A , 14%) as an orange oil, which was used without purification in the next step. M + (ES +) = (235, 100) for B; (221,100) for A
1H-NMR(DMSO-D6) (nur B): 1.18 (m, IH, -cHex); 1.37 (bm, 4H, -cHex); 1.65 (m, IH, -cHex); 1.73 (m, 2H, -cHex); 1.83 (m, 2H, -cHex); 3.46 (m, IH, -cHex); 3-76 (s, 6H, -OMe); 6.91 (d, J=9 Hz, IH, Aryl); 7.16 (dd, J=3.1 Hz, 9 Hz, IH, Aryl); 7.29 (d, J=3.1 Hz, IH, Aryl); 9.08 (s, IH, OH); 11.39 (s, IH, OH) 1 H-NMR (DMSO-D 6 ) (B only): 1.18 (m, IH, -hexex); 1.37 (bm, 4H, -hex); 1.65 (m, IH, -hex); 1.73 (m, 2H, -hex); 1.83 (m, 2H, -hex); 3.46 (m, IH, -hex); 3-76 (s, 6H, -OMe); 6.91 (d, J = 9 Hz, IH, aryl); 7.16 (dd, J = 3.1 Hz, 9 Hz, IH, aryl); 7.29 (d, J = 3.1 Hz, IH, aryl); 9.08 (s, IH, OH); 11.39 (s, IH, OH)
(79) : (2,5-Dihydroxyphenyl)-cyclohexylketon(79): (2,5-Dihydroxyphenyl) cyclohexyl ketone
Unter Schutzgas werden 84,3g (2,5-Dihydroxyphenyl)-cyclohexylketon in 550 mL Dichlormethan vorgelegt, auf O0C gekühlt und tropfenweise über einen Zeitraum von 30 min. mit einer Lösung von 68 mL BBr3 in 200 mL Dichlormethan versetzt. Nach 2h Nachrühren bei gegebener Temperatur wird die Reaktionsmischung auf 0,7L Eis gegossen, 30 min. nachgerührt und durch Zugabe von 400 mL ges. NaHCO3-LSg. neutralisiert. Nach Phasentrennung wurde die wässrige Phase mehrfach mit Dichlormethan extrahiert, die vereinigten organischen Phasen getrocknet und zur Trockene eingeengt. Es werden 37,7g (2,5-Dihydroxyphenyl)-cyclohexylketon (99%ig laut LC-MS) als Öl erhalten, welches ohne Aufreinigung im nächsten Schritt eingesetzt wurde. M+(ES+)= (221, 100) 1H-NMR(DMSO-D6): 1.19 (m, IH, -cHex); 1.35 (bm, 4H, -cHex); 1.67 (m, IH, -cHex); 1.78 (bm, 4H, -cHex); 3.34 (m, IH, -cHex); 6.81 (d, J=8.8 Hz, IH, Aryl); 6.97 (dd, J=2.9 Hz, 8.8 Hz, IH, Aryl); 7.20 (d, J=2.9 Hz, IH, Aryl); 9.08 (s, IH, OH); 11.37 (s, IH, OH)Under protective gas 84.3g (2,5-dihydroxyphenyl) cyclohexyl ketone are placed in 550 mL of dichloromethane, cooled to 0 0 C and dropwise over a period of 30 min. a solution of 68 mL BBr 3 in 200 mL dichloromethane. After 2 h stirring at a given temperature, the reaction mixture is poured onto 0.7 L of ice, 30 min. stirred and by adding 400 mL sat. NaHCO 3 -LSg. neutralized. After phase separation, the aqueous phase was extracted several times with dichloromethane, the combined organic phases were dried and concentrated to dryness. 37.7 g (2,5-dihydroxyphenyl) cyclohexyl ketone (99% according to LC-MS) are obtained as an oil, which was used without purification in the next step. M + (ES +) = (221, 100) 1 H-NMR (DMSO-D 6 ): 1.19 (m, IH, -cHex); 1.35 (bm, 4H, -hex); 1.67 (m, IH, -hex); 1.78 (bm, 4H, -hex); 3.34 (m, IH, -hex); 6.81 (d, J = 8.8 Hz, IH, aryl); 6.97 (dd, J = 2.9 Hz, 8.8 Hz, IH, aryl); 7.20 (d, J = 2.9 Hz, IH, aryl); 9.08 (s, IH, OH); 11.37 (s, IH, OH)
(80) : (S-Chlor-ZjS-dihydroxyphenyty-cyclohexylketon(80): (S-Chloro-Z j S-dihydroxyphenyty-cyclohexyl ketone
- O - - O -
Innerhalb von 1 h werden 29 g N-Chlorsuccinimid unter Stickstoff portionsweise zu einer Lösung von 36.7 g (2,5-Dihydroxyphenyl)-cyclohexylketon in 170 ml DMF gegeben. Die Reaktionslösung verfärbte sich braun und wird über Nacht bei RT gerührt. Das Reaktionsgemisch wird in 0.6 1 Wasser gegossen und mehrfach mit Dichlormethan extrahiert. Die vereinten organischen Phasen werden mehrfach mit Wasser gewaschen, über Na2SO4 getrocknet, filtriert und zur Trockne eingeengt. Es wurden 70g (3-Chlor-2,5-dihydroxyphenyl)-cyclohexylketon (50%ig laut LC-MS) als Feststoff erhalten, welches ohne Aufreinigung im nächsten Schritt eingesetzt wurde. M+(ES+)= (255, 100)Within 1 h, 29 g of N-chlorosuccinimide are added in portions under nitrogen to a solution of 36.7 g of (2,5-dihydroxyphenyl) cyclohexyl ketone in 170 ml of DMF. The reaction solution turned brown and is stirred at RT overnight. The reaction mixture is poured into 0.6 1 of water and extracted several times with dichloromethane. The combined organic phases are washed several times with water, dried over Na 2 SO 4 , filtered and concentrated to dryness. There were 70g (3-chloro-2,5-dihydroxyphenyl) cyclohexyl ketone (50% by LC-MS) as a solid, which was used without purification in the next step. M + (ES +) = (255, 100)
1H-NMR(DMSO-D6): 1.10-1.39 (bm, 5H, -cHex); 1.57-1.88 (m, 5H, -cHex); 3.35 (m, IH, -cHex); 7.16 (d, J=2.8 Hz, IH, Aryl); 7.28 (m, J=2.8 Hz, IH, Aryl); 9,50 (s, IH, OH); 11.96 (s, IH, OH) 1 H-NMR (DMSO-D 6 ): 1.10-1.39 (bm, 5H, -cHex); 1.57-1.88 (m, 5H, -hex); 3.35 (m, IH, -hex); 7.16 (d, J = 2.8 Hz, IH, aryl); 7.28 (m, J = 2.8 Hz, IH, aryl); 9.50 (s, IH, OH); 11.96 (s, IH, OH)
Biologische BeispieleBiological examples
Beispiel Nr. AExample No. A
Spodoptera frugiperda-Test (Spritzbehandlung)Spodoptera frugiperda test (spray treatment)
Lösungsmittel: 78 Gewichtsteile Aceton 1,5 Gewichtsteile DimethylformamidSolvent: 78 parts by weight of acetone 1.5 parts by weight of dimethylformamide
Emulgator: 0,5 Gewichtsteile AlkylarylpolyglykoletherEmulsifier: 0.5 part by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit den angegebenen Mengen Lösungsmittel und Emulgator und verdünnt das Konzentrat mit emulgatorhaltigem Wasser auf die gewünschte Konzentration.To prepare a suitable preparation of 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.
Maisblattscheiben (Zea mays) werden mit einer Wirkstoffzubereitung der gewünschten Konzentration gespritzt und nach dem Abtrocknen mit Raupen des Heerwurms (Spodoptera frugiperdä) besetzt.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).
Nach der gewünschten Zeit wird die Wirkung in % bestimmt. Dabei bedeutet 100 %, dass alle Raupen abgetötet wurden; 0 % bedeutet, dass keine Raupe abgetötet wurde.After the desired time, the effect is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillar has been killed.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele eine gute Wirksamkeit: siehe Tabelle In this test, z. For example, the following compounds of the preparation examples a good activity: see table
- -- -
Tabelle ATable A
Beispiel Nr. B Example No. B
Phaedon-Test (Spritzbehandlung)Phaedon test (spray treatment)
Lösungsmittel: 78 Gewichtsteile AcetonSolvent: 78 parts by weight of acetone
1,5 Gewichtsteile Dimethylformamid1.5 parts by weight of dimethylformamide
Emulgator: 0,5 Gewichtsteile AlkylarylpolyglykoletherEmulsifier: 0.5 part by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit den angegebenen Mengen Lösungsmittel und Emulgator und verdünnt das Konzentrat mit emulgatorhaltigem Wasser auf die gewünschte Konzentration.To prepare a suitable preparation of 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.
Chinakohlblattscheiben (Brassica pekinensis) werden mit einer Wirkstoffzubereitung der ge- wünschten Konzentration gespritzt und nach dem Abtrocknen mit Larven des Meerrettichblattkäfers (Phaedon cochleariae) besetzt.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).
Nach der gewünschten Zeit wird die Wirkung in % bestimmt. Dabei bedeutet 100 %, dass alle Käferlarven abgetötet wurden; 0 % bedeutet, dass keine Käferlarven abgetötet wurden.After the desired time, the effect is determined in%. 100% means that all beetle larvae have been killed; 0% means that no beetle larvae have been killed.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele gute Wirksam- keit: siehe Tabelle In this test, z. B. the following compounds of the preparation examples good activity: see table
- -- -
Tabelle BTable B
Beispiel Nr. CExample No. C
Aedes Aegypti-TestAedes Aegypti test
Lösungsmittel: 1000 Gewichtsteile DimethylsulfoxidSolvent: 1000 parts by weight of dimethyl sulfoxide
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man den Wirkstoff mit den angegebenen Mengen Lösungsmittel und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration.To produce a suitable preparation of active compound, the active compound is mixed with the stated amounts of solvent and the concentrate is diluted with water to the desired concentration.
Die Aedsae aegypti Larven (drittes Laevenstadium L3) werden mit einer Wirkstoffzubereitung der gewünschten Konzentration behandelt.The Aedsae aegypti larvae (third Laevstadium L3) are treated with an active compound preparation of the desired concentration.
Nach der gewünschten Zeit wird die Wirkung in % bestimmt. Dabei bedeutet 100 %, dass alle Aedsae aegypti abgetötet wurden; 0 % bedeutet, dass keine Aedsae aegypti abgetötet wurden und -1 bedeutet nicht auswertbar.After the desired time, 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.
Bei diesem Test zeigt z. B. die folgende Verbindung der Herstellungsbeispiele gute Wirksamkeit: siehe Tabelle In this test, z. B. the following compound of the preparation examples good activity: see table
- -- -
Tabelle CTable C

Claims

Patentansprüche claims
1. Verbindungen der Formel (I)1. Compounds of the formula (I)
in welcherin which
A1 für eine der Gruppierungen -CH2-CH=CCl2, -CH2-CH=CBr2, -CH2-CH=CClF, -CH2-CF=CCl2, -(CH2)2-CH=CF2) -CH2-CH=CBrCl, -CH2-CH=CBrF, -CF=CH- CH=CH2, -CH2-CF=CF-CH=CH2, -CH2-CH=CClCF3, -(CH2)2-C(Halogen)3, -(CH2)2-CH(Halogen)2, -CH2-CH(HaIOgCn)-CH(HaIOgCn)2, -CH2-CH=CClCH3 steht,A 1 for one of the groupings -CH 2 -CH = CCl 2 , -CH 2 -CH = CBr 2 , -CH 2 -CH = CClF, -CH 2 -CF = CCl 2 , - (CH 2 ) 2 -CH = CF 2) -CH 2 -CH = CBrCl, -CH 2 -CH = CBrF, -CF = CH-CH = CH 2 , -CH 2 -CF = CF-CH = CH 2 , -CH 2 -CH = CClCF 3 , - (CH 2 ) 2 -C (halogen) 3 , - (CH 2 ) 2 -CH (halo) 2 , -CH 2 -CH (HaIOgCn) -CH (HaIOgCn) 2 , -CH 2 -CH = CClCH 3 stands,
A2-X entweder für eine direkte Bindung oder für ein geradkettiges oder verzweigtes oder cyclisches Alkandiyl oder ein Alkendiyl mit jeweils bis zu 8 Kohlenstoffatomen, und welche jeweils gegebenenfalls in Anknüpfung an die Kohlenstoffkette ein Sauerstoffatom, Schwefelatom oder eine Gruppierung ausgewählt aus SO, SO2, NH, N(CrC4-Alkyl) enthält, steht oderA 2 -X either for a direct bond or for a straight-chain or branched or cyclic alkanediyl or an alkenediyl each having up to 8 carbon atoms, and which in each case optionally in connection with the carbon chain an oxygen atom, sulfur atom or a grouping selected from SO, SO 2 , NH, N (C r C 4 alkyl), is or
A2-X für -(CrC4-Alkyl)-(CO)-O-, (CrC4-Alkyl)-(CO)-(NH)-, -(C,-C4-Alkyl)-(CO)-[N- (C,-C4-Alkyl)]-, -(C,-C4-Alkyl)-(CO)-S-, -(C,-C4-Alkyl)-O-(CO)-, -(CrC4-Alkyl)- (NH)-(CO)-, -(CrC4-Alkyl)-[N-(C,-C4-Alkyl)]-(CO)-, -(CrC4-Alkyl)-S-(CO)-, -(C2-C8-Alkenyl)-(CO)-O-, -(C2-C8-Alkenyl)-(CO)-(NH)-, -(C2-C8-Alkenyl)-(CO)- [N-(Ci-C4-Alkyl)]-, -(C2-C8-Alkenyl)-(CO)-S-, -(C2-C8-Alkenyl)-O-(CO)-(C2-C8- Alkenyl)-(NH)-(CO-)-, -(Ci-C4-AIk^)-[N-(C1-C4-AUCyI)MCO)-, -(C2-C8-Alkenyl)- S-(CO)-, -(Ci-C4-Alkyl)-[N-(CrC4-Alkyl)]-(CO)-, -(C2-C8-Alkenyl)-S-(CO)-, -(C1- C4-Alkyl)-(SO2)-(NH)-, -(C2-C8-Alkenyl)-(CO)-S-, -(C2-C8-Alkenyl)-(SO2)-(NH)-, -(C,-C4-Alkyl)-O-N=C(R9)-, -(CrC8-Alkenyl)-O-N=C(R9)- steht, wobei R9 für C1- C4-Alkyl oder für Aryl steht, oder - -A 2 -X - (C r C 4 alkyl) - (CO) -O-, (C r C 4 alkyl) - (CO) - (NH) -, - (C, -C 4 alkyl) - (CO) - [N- (C 1 -C 4 -alkyl)] -, - (C 1 -C 4 -alkyl) - (CO) -S-, - (C 1 -C 4 -alkyl) -O - (CO) -, - (C r C 4 alkyl) - (NH) - (CO) -, - (C r C 4 alkyl) - [N- (C, -C 4 alkyl)] - ( CO) -, - (C r C 4 alkyl) -S- (CO) -, - (C 2 -C 8 alkenyl) - (CO) -O-, - (C 2 -C 8 alkenyl) - (CO) - (NH) -, (C 2 -C 8 -alkenyl) - (CO) - [N- (C 1 -C 4 -alkyl)] -, - (C 2 -C 8 -alkenyl) - (C 2 -C 8 -alkenyl) - CO) -S-, - (C 2 -C 8 -alkenyl) -O- (CO) - (C 2 -C 8 -alkenyl) - (NH) - (CO -) -, - (C 1 -C 4 - AIk ^) - [N- (C 1 -C 4 -alkyl) MCO) -, (C 2 -C 8 -alkenyl) -S- (CO) -, - (C 1 -C 4 -alkyl) - [N - (C r C 4 alkyl)] - (CO) -, - (C 2 -C 8 -alkenyl) -S- (CO) -, - (C 1 - C 4 alkyl) - (SO 2) - (NH) -, - (C 2 -C 8 alkenyl) - (CO) -S-, - (C 2 -C 8 alkenyl) - (SO 2 ) - (NH) -, - (C, -C 4- alkyl) -ON = C (R 9 ) -, - (C r C 8 -alkenyl) -ON = C (R 9 ) -, where R 9 is C 1 -C 4 -alkyl or aryl, or - -
A2-X für ein carbocyclisches gegebenenfalls ein- oder mehrfach ungesättigtes 5,6 oder 7-gliedriges Ringsystem oder für ein gegebenenfalls ein- oder mehrfach ungesättigtes 7-10-gliedriges bicyclisches Ringsystem steht, das gegebenenfalls ein- oder mehrfach durch Sauerstoff, Schwefel, Sulfonyl, Sulfoxyl, Carbonyl, NO, oder gegebenenfalls durch mit Alkyl substituierten Stickstoff unterbrochen und gegebenenfalls ein- oder mehrfach substituiert sein kann, wobei die Anknüpfung dieser Ringsysteme an den Oximsauerstoff immer über Kohlenstoff erfolgt und die Anknüpfung an den Rest R6 über Kohlenstoff oder ein Heteroatom (Stickstoff oder Schwefel) erfolgt,A 2 -X represents a carbocyclic, optionally mono- or polyunsaturated, 5,6 or 7-membered ring system or an optionally mono- or polyunsaturated 7-10-membered bicyclic ring system which is optionally mono- or polysubstituted by oxygen, sulfur, Sulfonyl, sulfoxyl, carbonyl, NO, or optionally interrupted by alkyl-substituted nitrogen and may optionally be mono- or polysubstituted, wherein the attachment of these ring systems to the oxime oxygen always takes place via carbon and the attachment to the radical R 6 via carbon or a Heteroatom (nitrogen or sulfur),
wobei zwischen X und R6 sich gegebenenfalls das verbrückende Elementwhere between X and R 6 is optionally the bridging element
befindet, in dem die Reste R21 und R22 unabhängig voneinander für Wasserstoff, Nitro, Hydroxy, Amino, Cyano, Cyanato, Thiocyanato, Formyl, Halogen, für jeweils gegebenenfalls durch Cyano, Halogen oder Ci-C6-Alkoxy substituiertes Alkyl, Alkoxy, Alkylthio, Alkylsulfϊnyl, Alkylsulfonyl, Alkylamino, Dialkylamino oder Alkylcarbonylamino mit jeweils 1 bis 4 Kohlenstoffatomen in den Alkyl- gruppen, für Ci-C4-Alkyl-carbonyl, Ci-C4-Alkoxy-carbonyl, Ci-C4-Alkoximino- formyl, Ci-C4-Alkoximino-acetyl, oder für C2-C4- Alkenyl oder C2-C4- Alkinyl stehen,is in which the radicals R 21 and R 22 are independently hydrogen, nitro, hydroxy, amino, cyano, cyanato, thiocyanato, formyl, halogen, each optionally substituted by cyano, halogen or Ci-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 -alkoxycarbonyl, C 1 -C 4 -alkoximino, formyl, C 1 -C 4 -alkoximino-acetyl, or C 2 -C 4 -alkenyl or C 2 -C 4 -alkynyl,
R1 für Wasserstoff, Nitro, Hydroxy, Amino, Cyano, Fluor, Chlor, Brom, Iod, oder für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Methoxy, Ethoxy, n- oder i- Propoxy substituiertes Ci -C6- Alkyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkyloxy, C3- C6- Alkenyl, C3-C6- Alkenyloxy, C3-C6-Alkinyl, C3-C6-Alkinyloxy, CrC6-Alkyl- carbonyloxy, Ci-C3-Alkylsulfonyl, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t- Butyl, Methoxy, Ethoxy, n- oder i-Propoxy, n-, i-, s- oder t-Butoxy, Methylthio,R 1 represents hydrogen, nitro, hydroxyl, amino, cyano, fluorine, chlorine, bromine, iodine, or represents in each case optionally cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy-substituted C 1 -C 6 -alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyloxy, C 3 - C 6 - alkenyl, C 3 -C 6 - alkenyloxy, C 3 -C 6 alkynyl, C 3 -C 6 alkynyloxy, C r C 6 -alkyl-carbonyloxy, C 1 -C 3 -alkylsulfonyl, 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- oder i-Propylthio, n-, i-, s- oder t-Butylthio, Methylamino, Ethyl- amino, n- oder i-Propylamino, n-, i-, s- oder t-Butylamino, Dimethylamino, Di- ethylamino, Dipropylamino, Acetylamino, Propionylamino, n- oder i-Butyroyl- amino, Methoximinomethyl, Ethoximinomethyl, Methoximinoethyl oder Ethox- iminoethyl steht, R2 für Wasserstoff, Nitro, Hydroxy, Amino, Cyano, Cyanato, Thiocyanato, Formyl, Halogen, für jeweils gegebenenfalls durch Cyano, Halogen oder durch CpCe- Alkoxy substituiertes Alkyl, Alkoxy, Alkylthio, Alkylsulfinyl, Alkylsulfonyl, Alkylamino, Dialkylamino oder Alkylcarbonylamino mit jeweils 1 bis 6 Kohlen- Stoffatomen in den Alkylgruppen, für Ci-Cβ-Alkyl-carbonyl, Ci-Cβ-Alkoxy- carbonyl, Ci-C6-Alkoximinoformyl, Ci-Cβ-Alkoximino-acetyl, oder für C2-C6- Alkenyl oder Ca-Cβ-Alkinyl steht,Ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, Diethylamino, dipropylamino, acetylamino, propionylamino, n- or i-butyroylamino, methoximinomethyl, ethoximinomethyl, methoximinoethyl or ethoximinoethyl, R 2 is hydrogen, nitro, hydroxyl, amino, cyano, cyanato, thiocyanato, formyl, halogen, each optionally substituted by cyano, halogen or by CpCe- alkoxy-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino or alkylcarbonylamino with in each case 1 to 6 carbon atoms in the alkyl groups, for C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkoxymino-formyl, C 1 -C 6 -alkoximino-acetyl, or for C 2 -C 6 - Alkenyl or Ca-Cβ-alkynyl,
R3 für Wasserstoff, Nitro, Hydroxy, Amino, Cyano, Halogen, für jeweils gegebenenfalls durch Cyano, Halogen oder Ci-C6-Alkoxy substituiertes Alkyl, Alkoxy, Alkylthio, Alkylamino, Dialkylamino oder Alkylcarbonylamino mit jeweils 1 bis 6R 3 is hydrogen, nitro, hydroxy, amino, cyano, halogen, in each case optionally substituted by cyano, halogen or Ci-C 6 alkoxy-substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or alkylcarbonylamino each having 1 to 6
Kohlenstoffatomen in den Alkylgruppen steht,Carbon atoms in the alkyl groups,
R4 für Wasserstoff, Nitro, Hydroxy, Amino, Cyano, Halogen, für jeweils gegebenenfalls durch Cyano, Halogen oder Ci -C6- Alkoxy substituiertes Alkyl, Alkoxy, Alkylthio, Alkylamino, Dialkylamino oder Alkylcarbonylamino mit jeweils 1 bis 6 Kohlenstoffatomen in den Alkylgruppen steht,R 4 is hydrogen, nitro, hydroxyl, amino, cyano, halogen, in each case optionally substituted by cyano, halogen or Ci -C 6 - alkoxy-substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or alkylcarbonylamino each having 1 to 6 carbon atoms in the alkyl groups stands,
R5 für Wasserstoff, ein geradkettiges oder verzweigtes oder cyclisches Halogen- alkanyl oder Halogenalkenyl mit jeweils bis zu 8 Kohlenstoffatomen für Aryl oder substituiertes Aryl steht,R 5 is hydrogen, a straight-chain or branched or cyclic haloalkanyl or haloalkenyl having in each case up to 8 carbon atoms is aryl or substituted aryl,
R6 für eine Alkenyl-Gruppierung, Alkinyl-Gruppierung mit jeweils 2 bis 6 Kohlen- stoffatomen oder Cycloalkenyl-Gruppierung mit 4 bis 6 Kohlenstoffatomen steht, welche gegebenenfalls substituiert ist durch mindestens einen Substituenten aus der Reihe Nitro, Cyano, Carboxy, Carbamoyl, Hydroxy, Carbonyl (C=O), Hydroximino (C=N-OH), CrC6-Alkoxy, CrC6-Alkoxy-carbonyl, C1-C6- Alkylamino, Di-(C i-C6-alkyl)-amino, Ci-Cö-Alkylamino-carbonyl, Ci-C6-Alkoxy- carbonylamino, Ci-Cö-Alkoxy-Ci-Cβ-alkoxy, Ci-C6-Alkoxyimino, Cs-Cβ-Alkenyl- oxy, C3-C6-Alkinyloxy, Cj-Cβ-Alkenyloxy-carbonyl, C3-C6-Alkinyloxy-carbonyl, C3-C6-Alkenyloxyimino, Ca-Cβ-Alkinyloxyimino, C3-C6-Cycloalkyl, Furyl, Benzo- furyl, Thienyl, Benzothienyl, Isoxazolyl, Benzisoxazolyl, Pyrazolyl, Pyridinyl, Pyrimidinyl, Pyrazinyl, Pyridazinyl, oderR 6 is an alkenyl grouping, alkynyl moiety having in each case 2 to 6 carbon atoms or cycloalkenyl moiety having 4 to 6 carbon atoms which is optionally substituted by at least one substituent selected from nitro, cyano, carboxy, carbamoyl, hydroxy , carbonyl (C = O), hydroxyimino (C = N-OH), C r C 6 alkoxy, C r C 6 alkoxy-carbonyl, C 1 -C 6 - alkylamino, di- (C iC 6 alkyl) amino, Ci-C ö alkylamino-carbonyl, Ci-C 6 alkoxy carbonylamino, Ci-C ö alkoxy-Ci-Cβ-alkoxy, Ci-C 6 alkoxyimino, Cs-Cβ-alkenyl oxy, C 3 -C 6 alkynyloxy, Cj-Cβ-alkenyloxy-carbonyl, C 3 -C 6 alkynyloxy-carbonyl, C 3 -C 6 -Alkenyloxyimino, Ca-Cβ-Alkinyloxyimino, C 3 -C 6 cycloalkyl, furyl, benzo - furyl, thienyl, benzothienyl, isoxazolyl, benzisoxazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, or
R6 für eine Gruppierung -A3-Z steht, wobei - -R 6 is a grouping -A 3 -Z, where - -
A3 für eine Einfachbindung oder für geradkettiges oder verzweigtes und gegebenenfalls durch Halogen oder C3-C6-Cycloalkyl substituiertes Alkandiyl mit 1 bis 6 Kohlenstoffatomen steht undA 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 für gegebenenfalls durch Nitro, Hydroxy, Mercapto, Amino, Formyl, Cyano, Carboxy, Carbamoyl, Halogen, Ci-C6-Alkyl, Ci-C6-Hydroxyalkyl,Z is optionally substituted by nitro, hydroxy, mercapto, amino, formyl, cyano, carboxy, carbamoyl, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -hydroxyalkyl,
Ci-Cβ-Halogenalkyl, Ci-C6-Alkyl-carbonyl, Ci-Q-Halogenalkyl-carbonyl, Ci-C6-Alkoxy, Ci-C6-Hydroxyalkoxy, CrC6-Halogenalkoxy, CpC6-AIk- oxy-carbonyl, CpC6-Halogenalkoxy-carbonyl, CpC6-Alkoxy-CpC6-alkyl, C,-C6-Halogenalkoxy-Ci-C6-alkyl, CrC2-Alkylendioxy, C,-C2-Haloalky- lendioxy, CpC6-Alkoxyimino-CpC6-alkyl, C2-C6- Alkenyl, C2-C6-Alkenyl- carbonyl, C2-C6-Halogenalkenyl, C2-C6-Halogenalkenyl-carbonyl, C2-C6- Alkenyloxy-Cj -C6-alkyl, C2-C6-Halogenalkenyloxy-C] -C6-alkyl, C2-C6- Alkinyl, C2-C6-Halogenalkinyl, C2-C6-Alkenyloxy, C2-C6-Alkenyloxy- carbonyl, C2-C6-Halogenalkenyloxy, C2-C6-Halogenalkenyloxy-carbonyl, C2-C6-Alkinyloxy, CrCβ-Alkinyloxy-carbonyl, C2-C6-Halogenalkinyloxy,Ci-Cβ-haloalkyl, Ci-C 6 alkyl-carbonyl, Ci-Q-haloalkyl-carbonyl, Ci-C 6 alkoxy, Ci-C6 hydroxyalkoxy, C r C 6 haloalkoxy, CpC 6 -AIk- oxy -carbonyl, CpC 6 haloalkoxy-carbonyl, CpC 6 alkoxy CpC 6 alkyl, C, -C 6 haloalkoxy-C 6 alkyl, C r C 2 alkylenedioxy, C, -C 2 -Haloalky- lendioxy, CpC 6 -alkoxyimino-CpC 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkenylcarbonyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkenyl-carbonyl, C 2 -C 6 - alkenyloxy Cj -C 6 alkyl, C 2 -C 6 haloalkenyloxy-C] to C 6 alkyl, C 2 -C 6 - alkynyl, C 2 -C 6 haloalkynyl, C 2 -C 6 alkenyloxy, C 2 -C 6 alkenyloxy carbonyl, C 2 -C 6 haloalkenyloxy, C 2 -C 6 haloalkenyloxy-carbonyl, C 2 -C 6 alkynyloxy, CrCβ alkynyloxy-carbonyl, C 2 -C 6 haloalkynyloxy,
C2-C6-Halogenalkinyloxy-carbonyl, C2-C6-Alkinyloxy-Ci-C6-alkyl, C2-C6- Halogenalkinyloxy-Ci-C6-alkyl, C3-C8-Cycloalkyl, C3-C8-Cycloalkyl- carbonyl, C3-C8-CyClOaIlCyI-C1 -C6-alkyl, C3-C8-Cycloalkyl-C,-C6-alkyl- carbonyl, Cs-Cs-Cycloalkyloxy, C3-C8-Cycloalkyloxy-carbonyl, C3-C8- Cycloalkyl-CrC6-alkoxy, C3-C8-Cycloalkyl-CrC6-alkoxy-carbonyl, C3-C8-C 2 -C 6 haloalkynyloxy-carbonyl, C 2 -C 6 alkynyloxy-Ci-C 6 alkyl, C 2 -C 6 - haloalkynyloxy-Ci-C 6 alkyl, C 3 -C 8 cycloalkyl, C 3 -C 8 -cycloalkylcarbonyl, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkyl-C, -C 6 -alkylcarbonyl, Cs-Cs-cycloalkyloxy, C 3 -C 8 cycloalkyloxycarbonyl, C 3 -C 8 cycloalkylC r C 6 alkoxy, C 3 -C 8 cycloalkylC r C 6 alkoxycarbonyl, C 3 -C 8 -
Cycloalkyloxy-CrC6-alkyl, C3-C8-Cycloalkyloxy-CrC6-alkoxy, C3-C8- Cycloalkyl-Ci-C6-alkoxy-C,-C6-alkyl, CrC6-Alkyl-carbonyl-C,-C6-alkyl, CrC6-Alkoxy-carbonyl-Ci-C6-alkyl, C,-C6-Alkylthio, CrC6-Halogen- alkylthio, CrCβ-Alkylsulfinyl, Ci-Ce-Halogenalkylsulfinyl, CrC6-Alkyl- sulfonyl, Ci-Cβ-Halogenalkylsulfonyl, C2-C6- Alkenylthio, C2-C6-Halogen- alkenylthio, C2-C6-Alkinylthio, C3-C6-Cycloalkylthio, C3-C6-Cycloalkyl- Ci-C6-alkylthio, Ci-C6-Alkylamino, CrCβ-Alkylamino-carbonyl, Di-(Cr C6-alkyl)-amino, Di-(Ci-C6-alkyl)-amino-carbonyl, CrC6-Alkyl-carbonyl- amino, Ci-Cβ-Halogenalkyl-carbonylamino, Ci-C6-Alkoxy-carbonylamino, Ci-Cft-Alkyl-aminocarbonylamino, oder durch Phenyl, Phenyloxy, Benzyl,CycloalkyloxyC r C 6 alkyl, C 3 -C 8 cycloalkyloxyC r C 6 alkoxy, C 3 -C 8 cycloalkyl-Ci-C 6 alkoxy-C, C 6 alkyl, C r C 6 alkyl-carbonyl-C, -C 6 alkyl, C r C 6 alkoxy-carbonyl-Ci-C 6 alkyl, C, -C 6 alkylthio, C r C 6-halo alkylthio, alkylsulfinyl CrCβ , Ci-Ce-haloalkylsulfinyl, C r C 6 alkyl sulfonyl, Ci-Cβ-haloalkylsulfonyl, C 2 -C 6 - alkenylthio, C 2 -C 6 halo-alkenylthio, C 2 -C 6 alkynylthio, C 3 -C 6 -cycloalkylthio, C 3 -C 6 cycloalkyl, Ci-C 6 alkylthio, Ci-C 6 -alkylamino, CrCβ-alkylamino-carbonyl, di- (Cr C 6 alkyl) amino, di (C -C 6 -alkyl) -amino-carbonyl, C r C 6 alkyl-carbonylamino, Ci-Cβ-haloalkyl-carbonylamino, Ci-C 6 alkoxy-carbonylamino, Ci-C ft alkyl-aminocarbonylamino, or by Phenyl, phenyloxy, benzyl,
Benzyloxy, Phenylamino, Benzylamino (wobei jeweils die Phenylgruppen gegebenenfalls durch Nitro, Hydroxy, Mercapto, Amino, Cyano, CpC6- Alkyl, Ci-C6-Halogenalkyl, Ci-C6-Alkyl-carbonyl, C2-C6-Alkenyl, C2-C6- Halogenalkenyl, C2-C6-Alkiyl, C2-C6-Halogenalkinyl, C]-C6-Alkoxy, Cp C6-Halogenalkoxy, C2-C6- Alkenyloxy, C2-C6-Halogenalkenyloxy, C2-C6- Benzyloxy, phenylamino, benzylamino (wherein the phenyl in each case optionally substituted by nitro, hydroxy, mercapto, amino, cyano, CpC 6 - alkyl, Ci-C 6 haloalkyl, Ci-C 6 alkyl-carbonyl, C 2 -C 6 alkenyl , C 2 -C 6 - haloalkenyl, C 2 -C 6 -Alkiyl, C 2 -C 6 haloalkynyl, C] -C6 alkoxy, Cp C 6 haloalkoxy, C 2 -C 6 - alkenyloxy, C 2 - C 6 haloalkenyloxy, C 2 -C 6 -
. ., ,
Alkinyloxy, Ci-C6-Alkylthio, C,-C6-Alkylsulfinyl, C,-C6-Alkylsulfonyl oder Ci-C6-Alkoxy-carbonyl substituiert sind) substituiertes, Aryl oder monocyclisches oder bicyclisches Heteroaryl mit bis zu 10 Kohlenstoffatomen und mindestens einem Heteroatom aus der Reihe N (Stickstoff, 1 i bis 5 N-Atome), O (Sauerstoff, 1 oder 2 O-Atome), Schwefel (1 oder 2 S-Alkynyloxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl or C 1 -C 6 -alkoxycarbonyl are substituted), aryl or monocyclic or bicyclic heteroaryl having up to 10 carbon atoms and at least one heteroatom from the series N (nitrogen, 1 i to 5 N atoms), O (oxygen, 1 or 2 O atoms), sulfur (1 or 2 S atoms)
Atome) steht und gegebenenfalls ersatzweise oder zusätzlich eine SO- oder SO2-Gruppierung, und gegebenenfalls zusätzlich eine Carbonyl- Gruppierung (C=O) und/oder einer Thiocarbonyl-Gruppierung (C=S) als Bestandteil des Heterocyclus enthält, oderAtoms) and optionally substituted or additionally an SO or SO 2 group , and optionally additionally a carbonyl group (C = O) and / or a thiocarbonyl group (C = S) contains as part of the heterocycle, or
R für eine der GruppierungenR for one of the groupings
steht, worinstands in which
A3 für eine Einfachbindung oder für eine gegebenenfalls einfach oder mehrfach durch Halogen oder C3-C8 Cycloalkyl substituierte Q-C6 Alkylenbrücke steht,A 3 represents a single bond or a QC 6 alkylene bridge which is optionally monosubstituted or polysubstituted by halogen or C 3 -C 8 cycloalkyl,
M für Sauerstoff oder NOR7 steht, wobeiM is oxygen or NOR 7 , where
R7 für Wasserstoff; CrCi2Alkyl, C3-C8Cycloalkyl, Cj-CAlkylcarbonyl, C2-C6Al- kenyl, C2-CoAIk)HyI, Aryl, Heterocyclyl oder Benzyl steht, wobei die Alkyl, Cycloalkyl, Alkenyl und Alkynyl Reste unsubstituiert sind oder gegebenenfalls ein- bis fünffach mit einem Rest aus der folgender Gruppe substituiert sind: Halogen,-N3, CN, NO2, OH, SH, Ci-C6AIkOXy, C,-C6HaloAlkoxy, C2-C6Al- kenyloxy, Q-C^aloalkenyloxy, CrCβAlkynyloxy, CrCδHaloalkynyloxy, C3-Cg- Cycloalkyl-Ci-CfrAlkoxy, Ci-CβAlkylcarbonyl, CpCβHaloalkylcarbonyl, Ci-C6AIk- oxycarbonyl, Ci-C6Alkylcarbonyl-Ci-C6Alkyl, Ci-CδAlkoxycarbonyl-Ci-CδAlkyl, d-C6Alkylthio, C2-C6AUCyUhIo, CrC^kynyltru^ C3-C6Cycloalkyl- Cr CδAlkylthio, C3-C<jHaloalkynyl, C2-C6Haloalkenylthio, Ci-CβHaloalkylthio, C,-R 7 is hydrogen; C r -C 2 alkyl, C 3 -C 8 cycloalkyl, Cj-CAlkylcarbonyl, C 2 -C 6 alkenyl, C 2 -CoAIk) HYI, aryl, heterocyclyl or benzyl, wherein the alkyl, cycloalkyl, alkenyl and alkynyl radicals unsubstituted or optionally substituted one to five times with a radical from the following group: halogen, -N 3 , CN, NO 2 , OH, SH, Ci-C 6 alkoxy, C, -C 6 haloalkoxy, C 2 -C 6 Al kenyloxy, QC ^ aloalkenyloxy, CrCβAlkynyloxy, CrC δ Haloalkynyloxy, C 3 -Cg- cycloalkyl-C f rAlkoxy, Ci-CβAlkylcarbonyl, CpCβHaloalkylcarbonyl, Ci-C 6 AIk- oxycarbonyl, Ci-C 6 alkylcarbonyl-Ci- C 6 alkyl, Ci-C δ alkoxycarbonyl-Ci-C δ alkyl, dC 6 alkylthio, C 2 -C 6 AUCyUhIo, CrC ^ ^ kynyltru C 3 -C 6 cycloalkyl C r C δ alkylthio, C 3 -C <jHaloalkynyl , C 2 -C 6 haloalkenylthio, Ci-CβHaloalkylthio, C, -
C6AIkOXy-CrC6AIlCyI, Ci-C6HaIOaIkOXy-Ci-C6Al]CyI, C∑-CeAlkenyloxy-Ci-CδAl- kyl, C2-C6HaIOaIkCHyIoXy-Ci-C6AIlCyI, C3-C6AUCyHyIoXy-C1-C6AIlCyI, NH2, NHC2- CβAlkenyl, C2-C6Haloalkenyl, C3-C6AIkJTIyI, C3-C8Cycloalkyl, C3-C8Cycloalkyl- Ci-C6AIlCyI, CpC6AIkOXy, Ci-C6HaIOaIkOXy, C2-C6Alkenyloxy, C2-C6HaIo- alkenyloxy, C3-C6AIkJTIyIoXy, C3-C6HaIOaIk)TIyIoXy, C3-CgCyClOaIlCyI-CpC6AIk- oxy, Ci-C6Alkylcarbonyl, Ci-CβHaloalkyl- Carbonyl, CpCδAlkoxycarbonyl, Cp CöAlkylcarbonyl-Ci-CeAlkyl, CpCeAlkoxycarbonyl- Ci-C6Alkyl, Ci-C6Alkylthio, C2-C6Alkenylthio, C3-C6Alkynylthio, C3-C6Cycloalkyl-Ci-C6Alkylthio, C3-C6HaIo- alkynyl, C2-C6Haloalkenylthio, Ci-CeHaloalkylthio, Ci-C6AIkOXy-Ci-C6AIlCyI, C,-C 6 alkoxy-CrC 6 AlCliI, Ci-C 6 haloalkoxy-Ci-C 6 Al] CyI, C Σ -CeAlkenyloxy-Ci-C δ alkyl, C 2 -C 6 haloalkyl-Cyanyl-Ci-C 6 AIlCyI, C 3 -C 6 AUCyHyIoXy-C 1 -C 6 AlCl yI, NH 2 , NHC 2 -Cβ alkenyl, C 2 -C 6 haloalkenyl, C 3 -C 6 alkyl, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkyl-C C 6 AIlCyI, CpC 6 -alkoxy, Ci-C 6 HaIOaIkOXy, C 2 -C 6 alkenyloxy, C 2 -C 6 halo- alkenyloxy, C 3 -C 6 alkyl-hexyl, C 3 -C 6 haloalkyl), TIyIoXy, C 3 -CgCyClOAlCl-CpC 6 alkoxy, Ci-C 6 alkylcarbonyl, Ci-CβHaloalkyl- carbonyl, CpC δ alkoxycarbonyl, Cp C ö alkylcarbonyl Ci-CeAlkyl, CpCeAlkoxycarbonyl- Ci-C 6 alkyl, Ci-C 6 alkylthio, C 2 -C 6 alkenylthio, C 3 -C6Alkynylthio, C 3 -C 6 cycloalkyl-Ci-C 6 alkylthio, C 3 -C 6 halo- alkynyl, C 2 -C 6 Haloalkenylthio, Ci-CeHaloalkylthio, Ci-C 6 -alkoxy-Ci-C 6 AIlCyI, C, -
CδHaloalkoxy-Ci-CδAlkyl, C2-C6AIkBHyIoXy-Ci-C6AIlCyI, C2-C6Haloalkenyloxy- Ci-C6Alkyl, C3-C6AHcJTIyIoXy-Ci-C6AIlCyI und N(Ci-C6AIlCyI)2, wobei die beiden Alkylgruppen unabhängig voneinander CpCβAlkylcarbonylamino, CpC6HaIo- alkylcarbonylamino, Ci-CβAlkoxycarbonylamino und CpCöAlkylaminocarbonyl- amino sein können,C δ haloalkoxy-Ci-C δ alkyl, C 2 -C 6 AlkBHyIoXy-Ci-C 6 AllCyI, C 2 -C 6 haloalkenyloxy-Ci-C 6 alkyl, C 3 -C 6 AHcJTIyIoXy-Ci-C 6 AIlCyI and N (Ci-C 6 AIlCyI) 2 wherein the two alkyl groups CpCβAlkylcarbonylamino, CpC alkylcarbonylamino independently 6 halo-, C CβAlkoxycarbonylamino and CpC ö alkylaminocarbonyl amino may be,
W für *C(R32R33) oder *C(R32R33)C(R34R35) steht und wobei der Stern „*"W stands for * C (R 32 R 33 ) or * C (R 32 R 33 ) C (R 34 R 35 ) and where the star "*"
die Anbindung an Sauerstoff bedeutet und wobei R32 bis R35 jeweils unabhängig voneinander für Halogen, CpC4Alkyl, CpC4AIkOXy(CpC4)Al]CyI oder HaIo(Cp C4)Alkyl stehen können,the bond to oxygen and wherein R 32 to R 35 may each independently be halogen, CpC 4 alkyl, CpC 4 alkoxy (CpC 4 ) Al] CyI or halo (Cp C 4 ) alkyl,
n Werte von O bis 3 annehmen kann,n can assume values from 0 to 3,
R8 für Wasserstoff, Halogen, HaIo(CpC4) Alkyl, C3-C6Cycloalkyl, C2-C5Alkenyl, C2- C5Alkynyl, CpCφHaloalkyl, CpC4Alkoxy, CrC4-Haloalkoxy, CpC4Alkylthio, Cp QHaloalkylthio, CrC4Alkylsulfonyl, CrC4Haloalkylsulfonyl, Nitro, Cyano, Aryl, Alkylcarbonylamino, Arylcarbonylamino und CpC4Alkxycarbonylamino steht,R 8 is hydrogen, halogen, Haio (CPC 4) alkyl, C 3 -C 6 cycloalkyl, C 2 -C 5 alkenyl, C 2 - C 5 alkynyl, CpCφHaloalkyl, CpC 4 alkoxy, C r C 4 haloalkoxy, CpC 4 Alkylthio, Cp Q haloalkylthio, C r C 4 alkylsulfonyl, C r C 4 haloalkylsulfonyl, nitro, cyano, aryl, alkylcarbonylamino, arylcarbonylamino and CpC 4 alkoxycarbonylamino,
R10 und R11 jeweils unabhängig voneinander für Wasserstoff, Halogen, Hydroxy, (CpR 10 and R 11 are each independently hydrogen, halo, hydroxy, (Cp
C4) Alkyl, HaIo(CpC4) Alkyl oder (CpC4) Alkoxy oder zusammen für Carbonyl, -0-CH2-CH2-O-, S-CH2-CH2-S, Ketal, Thioketal oder NOR12 steht, wobeiC 4 ) alkyl, halo (CpC 4 ) alkyl or (CpC 4 ) alkoxy or together for carbonyl, -O-CH 2 -CH 2 -O-, S-CH 2 -CH 2 -S, ketal, thioketal or NOR 12 stands, where
R12 für (CpC3)Alkyl, (CpC3)AIkOXy(CpC3) Alkyl, Aryl-(C,-C3)Alkyl, (C2-C4)alkenyl- (C,-C3)Alkyl, Halo(C2-C4)Alkenyl-(Cl -C3)Alkyl, di(C,-C3)Alkylphosphonat, Formyl, (CrC3)Alkylcarbonyl,R 12 is (CpC 3 ) alkyl, (CpC 3 ) alkoxy (CpC 3 ) alkyl, aryl (C, -C 3 ) alkyl, (C 2 -C 4 ) alkenyl (C, -C 3 ) alkyl, halo (C 2 -C 4) alkenyl, (Cl-C3) alkyl, di (C, -C 3) alkylphosphonate, formyl, (C r C 3) alkylcarbonyl,
HaIo(Cp C3)Alkylcarbonyl, (CrC3)Alkoxy(CrC3)Alkylcarbonyl, Arylcarbonyl und (CrC3)Alkylsulfonyl steht. Halo (Cp C 3 ) alkylcarbonyl, (C r C 3 ) alkoxy (C r C 3 ) alkylcarbonyl, arylcarbonyl and (C r C 3 ) alkylsulfonyl.
. _, _
2. Verbindungen der Formel (I) gemäß Anspruch 1 , dadurch gekennzeichnet dass2. Compounds of formula (I) according to claim 1, characterized in that
A1 für eine der GruppierungenA 1 for one of the groupings
-CH2-CH=CCl2, -CH2-CH=CBr2, -CH2-CH=CClF, -CH2-CH=CBrCl, -CH2- CH=CBrF steht,-CH 2 -CH = CCl 2 , -CH 2 -CH = CBr 2 , -CH 2 -CH = CClF, -CH 2 -CH = CBrCl, -CH 2 - CH = CBrF,
A2-X für ein geradkettiges oder verzweigtes Alkandiyl oder Alkendiyl mit jeweils bis zuA 2 -X for a straight-chain or branched alkanediyl or alkenediyl, each with up to
8 Kohlenstoffatomen steht, welches jeweils gegebenenfalls innerhalb der Kohlenstoffkette durch ein Sauerstoffatom, Schwefelatom oder eine Gruppierung ausgewählt aus SO, SO2, NH, N(C]-C4-Alkyl) unterbrochen sein kann oder8 carbon atoms, each of which may optionally be interrupted within the carbon chain by an oxygen atom, sulfur atom or a grouping selected from SO, SO 2 , NH, N (C] -C 4 alkyl) or
A2-X für -(CrC4-Alkyl)-(CO)-O-, -(C1-C4-AIlCyI)-(CO)-(NH)-, -(C,-C4-Alkyl)-(CO)-[N- (C-C4-Alkyl)]-, -(C1-C4-AIlCyIHCO)-S-, (C2-C8-Alkenyl)-(CO)-O-, -(C2-C8-A 2 -X - (C r C 4 alkyl) - (CO) -O-, - (C 1 -C 4 -alkyl) - (CO) - (NH) -, - (C, -C 4 - Alkyl) - (CO) - [N- (CC 4 -alkyl)] -, - (C 1 -C 4 -alkylCh) -S-, (C 2 -C 8 -alkenyl) - (CO) -O-, - (C 2 -C 8 -
Alkenyl)-(CO)-(NH)-, -(C2-C8-Alkenyl)-(CO)-[N-(C,-C4-Alkyl)]-, -(C2-C8- Alkenyl)-(CO)-S, Piperidyl oder Piperazinyl, -(CrC4-Alkyl)-O-N=C(R9)-, -(C1-C6- steht, wobei R9 entweder für Methyl oder für Aryl steht, undAlkenyl) - (CO) - (NH) -, - (C 2 -C 8 alkenyl) - (CO) - [N- (C 1 -C 4 alkyl)] -, - (C 2 -C 8 - alkenyl) - (CO) -S, piperidyl or piperazinyl, - (C r C 4 alkyl) -ON = C (R 9) -, - (C 1 -C 6 - wherein R 9 is either methyl or aryl, and
wobei sich zwischen X und R6 gegebenenfalls das verbrückende Elementwhere between X and R 6 optionally the bridging element
befindet, in dem die Reste R21 und R22 R21 und R22 unabhängig voneinander für Wasserstoff, Nitro, Hydroxy, Amino, Cyano, Cyanato, Thiocyanato, Formyl, Halogen oder Methyl stehen können,in which the radicals R 21 and R 22 R 21 and R 22 independently of one another may be hydrogen, nitro, hydroxyl, amino, cyano, cyanato, thiocyanato, formyl, halogen or methyl,
R1 für Wasserstoff, Nitro, Hydroxy, Cyano, Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-Propyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio, Ethylthio, n- oder i-Propylthio, Methylamino, Ethylamino, n- oder i-Propylamino, Dimethylamino oder für die Gruppierung -O-A1 steht, wobei A1 eine der vorstehend angebenenenR 1 is 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 the grouping -OA 1 , wherein A 1 is one of the abovementioned
Bedeutungen hat,Has meanings
R2 für Wasserstoff, Nitro, Cyano, Cyanato, Thiocyanato, Formyl, Halogen, für jeweils gegebenenfalls durch Cyano, Halogen oder durch CrC5-Alkoxy substituiertes Alkyl, Alkoxy, Alkylthio, Alkylamino, Dialkylamino oder Alkylcarbonyl- amino mit jeweils 1 bis 5 Kohlenstoffatomen in den Alkylgruppen, für Ci-C5- Alkyl-carbonyl, Ci-C5-Alkoxy-carbonyl, CrCs-Alkoximinoformyl, Ci-C5-Alkox- imino-acetyl, oder für C2-C5-Alkenyl oder C2-C5-Alkinyl steht, - o -R 2 is hydrogen, nitro, cyano, cyanato, thiocyanato, formyl, halogen, in each case optionally substituted by cyano, halogen or by C r C 5 alkoxy-substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or alkylcarbonylamino having 1 to 5 carbon atoms in the alkyl groups, for Ci-C 5 - alkyl-carbonyl, Ci-C 5 -alkoxycarbonyl, CrCs-Alkoximinoformyl, Ci-C 5 alkox-imino-acetyl, or for C 2 -C 5 alkenyl or C 2 -C 5 -alkynyl, - o -
R3 für Wasserstoff, Nitro, Halogen, für jeweils gegebenenfalls durch Cyano, Halogen oder CrC5-Alkoxy substituiertes Alkyl, Alkoxy, Alkylthio oder Alkylamino mit jeweils 1 bis 5 Kohlenstoffatomen in den Alkylgruppen steht,R 3 is hydrogen, nitro, halogen, in each case optionally cyano, halogen or C r C 5 alkoxy-substituted alkyl, alkoxy, alkylthio or alkylamino having in each case 1 to 5 carbon atoms in the alkyl groups,
R4 für Wasserstoff, Nitro, Halogen, für jeweils gegebenenfalls durch Cyano, Halogen oder Ci-C5-Alkoxy substituiertes Alkyl, Alkoxy, Alkylthio oder Alkylamino mit jeweils 1 bis 5 Kohlenstoffatomen in den Alkylgruppen steht,R 4 is 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,
R5 für eine Alkanyl-Gruppierung, eine Alkinyl-Gruppierung mit jeweils 2 bis 5 Kohlenstoffatomen oder eine Cycloalkanyl-Gruppierung mit 4 bis 6 Kohlenstoffatomen steht, welche mindestens einen Substituenten aus der Reihe Nitro, Cyano, Carboxy, Carbamoyl, Hydroxy, Carbonyl (C=O), Hydroximino (C=N-OH), C1-C5-R 5 is an alkanyl grouping, an alkynyl grouping each having 2 to 5 carbon atoms, or a cycloalkanyl grouping having 4 to 6 carbon atoms which have at least one substituent selected from nitro, cyano, carboxy, carbamoyl, hydroxy, carbonyl (C = O), hydroximino (C = N-OH), C 1 -C 5 -
Alkoxy, Ci-C5-Alkoxy-carbonyl, Ci -C5- Alkylamino, Di-(Ci -C4-alkyl)-amino, Cr C5-Alkylamino-carbonyl, Ci-Cs-Alkoxy-carbonylamino, CrC5-Alkoxy-Ci-C5- alkoxy, Ci-C5-Alkoxyimino, C3-C5-Alkenyloxy, C3-C5-Alkinyloxy, C3-C5- Alkenyloxy-carbonyl, CrCs-Alkinyloxy-carbonyl, C3-C5-Alkenyloxyimino, C3-C5- Alkinyloxyimino, C3-C6-Cycloalkyl enthält,Alkoxy, Ci-C5 alkoxycarbonyl, Ci -C5 - alkylamino, di- (Ci -C 4 alkyl) amino, C r C 5 alkylamino-carbonyl, Ci-Cs-alkoxy-carbonylamino, C r C 5 alkoxy-Ci-C 5 - alkoxy, Ci-C 5 -alkoxyimino, C 3 -C 5 alkenyloxy, C 3 -C 5 alkynyloxy, C 3 -C 5 - alkenyloxy-carbonyl, alkinyloxy-carbonyl CRCS , C 3 -C 5 -alkenyloxyimino, C 3 -C 5 -alkynyloxyimino, C 3 -C 6 -cycloalkyl,
R6 für eine Alkenyl-Gruppierung, eine Alkinyl-Gruppierung mit jeweils 2 bis 6 Kohlenstoffatomen oder eine Cycloalkenyl-Gruppierung mit 4 bis 6 Kohlenstoffatomen steht, welche gegebenenfalls substituiert ist durch mindestens einen Substituenten aus der Reihe Nitro, Cyano, Carboxy, Carbamoyl, Hydroxy, Carbonyl (C=O), Hydroximino (C=N-OH), CrC4-Alkoxy, Ci-C4-Alkoxy-carbonyl,R 6 is an alkenyl grouping, an alkynyl grouping each having 2 to 6 carbon atoms or a cycloalkenyl grouping having 4 to 6 carbon atoms, which is optionally substituted by at least one substituent selected from nitro, cyano, carboxy, carbamoyl, hydroxy , carbonyl (C = O), hydroxyimino (C = N-OH), C r C 4 alkoxy, Ci-C4-alkoxy-carbonyl,
Ci-GrAlkylamino, Di-(C i-C4-alkyl)-amino, Ci-C4-Alkylamino-carbonyl, Ci-C4- Alkoxy-carbonylamino, Ci-d-Alkoxy-Ci-Cβ-alkoxy, Ci-C4-Alkoxyimino, C3-C4- Alkenyloxy, C3-C4-Alkinyloxy, C3-C4-Alkenyloxy-carbonyl, C3-C4-Alkinyloxy- carbonyl, C3-C4-Alkenyloxyimino, C3-C4-Alkinyloxyimino, C3-C6-Cycloalkyl, Furyl, Benzofuryl, Thienyl, Benzothienyl, Isoxazolyl, Benzisoxazolyl, Pyrazolyl,Ci-GrAlkylamino, di- (C iC 4 alkyl) amino, Ci-C4-alkylamino-carbonyl, Ci-C 4 - alkoxy-carbonylamino, Ci-d-alkoxy-Ci-Cβ-alkoxy, Ci-C4- Alkoxyimino, C 3 -C 4 -alkenyloxy, C 3 -C 4 -alkynyloxy, C 3 -C 4 -alkenyloxycarbonyl, C 3 -C 4 -alkynyloxycarbonyl, C 3 -C 4 -alkenyloxyimino, C 3 - C 4 alkynyloxyimino, C 3 -C 6 cycloalkyl, furyl, benzofuryl, thienyl, benzothienyl, isoxazolyl, benzisoxazolyl, pyrazolyl,
Pyridinyl, Pyrimidinyl, Pyrazinyl, Pyridazinyl steht, oderPyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, or
R6 für eine Gruppierung -A3-Z steht, wobeiR 6 is a grouping -A 3 -Z, where
A3 bevorzugt für eine Einfachbindung oder für geradkettiges oder verzweigtes und gegebenenfalls durch Halogen oder C3-C6-Cycloalkyl substituiertes Alkandiyl mit 1 bis 6 Kohlenstoffatomen steht undA 3 preferably represents a single bond or represents straight-chain or branched alkanediyl having 1 to 6 carbon atoms and optionally substituted by halogen or C 3 -C 6 -cycloalkyl, and
Z für jeweils gegebenenfalls durch Nitro, Hydroxy, Amino, Formyl, Cyano,Z is each optionally substituted by nitro, hydroxy, amino, formyl, cyano,
Carboxy, Carbamoyl, Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- - -Carboxy, carbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- - -
oder t-Butyl, Fluormethyl, Chlormethyl, Difluormethyl, Dichlormethyl, Trifluor- methyl, Trichlormethyl, Fluorethyl, Chlorethyl, Difluorethyl, Dichlorethyl, Chlorfluorethyl, Trifluorethyl, Trichlorethyl, Chlordifluorethyl, Fluoφropyl, Chloφropyl, Difluorpropyl, Dichlorpropyl, Trifluoφropyl, Fluor-i-propyl, Difluor- i-propyl, Trifluor-i-propyl, Tetrafluor-i-propyl, Pentafluor-i-propyl, Methoxy,or t-butyl, fluoromethyl, chloromethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, fluoroethyl, chloroethyl, difluoroethyl, dichloroethyl, chlorofluoroethyl, trifluoroethyl, trichloroethyl, chlorodifluoroethyl, fluoφropyl, chloφropyl, difluoropropyl, dichloropropyl, trifluoropropyl, fluoro-i-propyl , Difluoro-i-propyl, trifluoro-i-propyl, tetrafluoro-i-propyl, pentafluoro-i-propyl, methoxy,
Ethoxy, n- oder i-Propoxy, Fluormethoxy, Difluormethoxy, Trifluormethoxy, Fluordichlormethoxy, Chlordifluormethoxy, Fluorethoxy, Chlorethoxy, Difluor- ethoxy, Dichlorethoxy, Trifluorethoxy, Fluoφropoxy, Methoxycarbonyl, Ethoxycarbonyl, Fluorethoxycarbonyl, Chlorethoxycarbonyl, Methoxymethyl, Ethoxymethyl, n- oder i-Propoxymethyl, Methoxyethyl, Ethoxyethyl, n- oder i-Ethoxy, n- or i-propoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, fluorodichloromethoxy, chlorodifluoromethoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, trifluoroethoxy, fluoφropoxy, methoxycarbonyl, ethoxycarbonyl, fluoroethoxycarbonyl, chloroethoxycarbonyl, methoxymethyl, ethoxymethyl, n- or i- Propoxymethyl, methoxyethyl, ethoxyethyl, n- or i-
Propoxyethyl, Ethenyl, Propenyl, Butenyl, Fluorethenyl, Chlorethenyl, Difluorethenyl, Dichlorethenyl, Trifluorethenyl, Trichlorethenyl, Propenyl- oxymethyl, Butenyloxymethyl, Propenyloxyethyl, Butenyloxyethyl, Ethinyl, Propinyl, Butinyl, Propenyloxy, Butenyloxy, Fluoφropenyloxy, Chloφropenyl- oxy, Fluorbutenyloxy, Chlorbutenyloxy, Propenyloxycarbonyl, Butenyloxy- carbonyl, Propinyloxy, Butinyloxy, Propinyloxycarbonyl, Butinyloxycarbonyl, Propinyloxymethyl, Butinyloxymethyl, Propinyloxyethyl, Butinyloxyethyl, Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclopropylcarbonyl, Cyclobutylcarbonyl, Cyclopentylcarbonyl, Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl, Cyclohexylmethyl, Cyclopropylmethylcarbonyl, Cyclobutylmethylcarbonyl,Propyloxyethyl, ethenyl, propenyl, butenyl Propenyloxycarbonyl, butenyloxycarbonyl, propynyloxy, butynyloxy, propynyloxycarbonyl, butynyloxycarbonyl, propynyloxymethyl, butynyloxymethyl, propynyloxyethyl, butynyloxyethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethylcarbonyl, cyclobutylmethylcarbonyl,
Cyclopentylmethylcarbonyl, Cyclopropyloxy, Cyclobutyloxy, Cyclopentyloxy, Cyclohexyloxy, Cyclopropyloxycarbonyl, Cyclobutyloxycarbonyl, Cyclopentyl- oxycarbonyl, Cyclohexyloxycarbonyl, Cyclopropylmethoxy, Cyclobutylmethoxy, Cyclopentylmethoxy, Cyclohexylmethoxy, Cyclopropylmethoxycarbonyl, Cyclobutylmethoxycarbonyl, Cyclopentylmethoxycarbonyl,Cyclopentylmethylcarbonyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropyloxycarbonyl, cyclobutyloxycarbonyl, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethoxycarbonyl, cyclobutylmethoxycarbonyl, cyclopentylmethoxycarbonyl,
Cyclohexylmethoxycarbonyl, Cyclopropylmethoxymethyl, Cyclo- butylmethoxymethyl, Cyclopentylmethoxymethyl, Cyclopropyloxymethoxy, Cyclobutyloxymethoxy, Cyclopentyloxymethoxy, Acetylmethyl, Propionylmethyl, n- oder i-Butyroylmethyl, Acetylethyl, Propionylethyl, Methoxycarbonylmethyl, Ethoxycarbonylmethyl, n- oder i-Propoxycarbonylmethyl, Methoxycarbonylethyl,Cyclohexylmethoxycarbonyl, cyclopropylmethoxymethyl, cyclobutylmethoxymethyl, cyclopentylmethoxymethyl, cyclopropyloxymethoxy, cyclobutyloxymethoxy, cyclopentyloxymethoxy, acetylmethyl, propionylmethyl, n- or i-butyroylmethyl, acetylethyl, propionylethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, n- or i-propoxycarbonylmethyl, methoxycarbonylethyl,
Ethoxycarbonylethyl, n- oder i-Propoxycarbonylethyl, Methylthio, Ethylthio, n- oder i-Propylthio, Difluormethylthio, Trifluormethylthio, Chlordifluormethylthio, Methylsulfinyl, Ethylsulfinyl, Trifluormethylsulfinyl, Methylsulfonyl, Ethyl- sulfonyl, Trifluormethylsulfonyl, Propenylthio, Butenylthio, Fluoφropenylthio, Chloφropenylthio, Fluorbutenylthio, Chlorbutenylthio, Propinylthio, Butinylthio,Ethoxycarbonylethyl, n- or i-propoxycarbonylethyl, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, methylsulfinyl, ethylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, trifluoromethylsulfonyl, propenylthio, butenylthio, fluoφropenylthio, cholφropenylthio, fluorobutenylthio, Chlorobutenylthio, propynylthio, butynylthio,
Cyclopropylthio, Cyclobutylthio, Cyclopentylthio, Cyclohexylthio, Cyclopropyl- - -Cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropyl - -
methylthio, Cyclobutylmethylthio, Cyclopentylmethylthio, Methylamino, Ethyl- amino, n- oder i-Propylamino, Methylaminocarbonyl, Ethylaminocarbonyl, n- oder i-Propylaminocarbonyl, Dimethylamino, Diethylamino, Dimethylaminocarbonyl, Diethylaminocarbonyl, Acetylamino, Propionylamino, n- oder i-Butyroylamino, Methoxycarbonylamino, Ethoxycarbonylamino, n- oder i-Propoxycarbonylamino, Methylaminocarbonylamino, Ethylaminocarbonylamino, n- oder i-Propylamino- carbonylamino, oder durch Phenyl, Phenyloxy, Benzyl, Benzyloxy, Phenylamino, Benzylamino (wobei jeweils die Phenylgruppen gegebenenfalls durch Nitro, Hydroxy, Mercapto, Amino, Cyano, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Trifluormethyl, Methoxy, Ethoxy, n- oder i-Propoxy, Difluormethoxy, Tri- fluormethoxy, Fluorethoxy, Difluorethoxy, Trifluorethoxy, Propenyloxy, Butenyloxy, Propinyloxy, Butinyloxy, Propinylthio, Butinylthio, Methylsulfmyl, Ethylsulfϊnyl, Methylsulfonyl, Ethylsulfonyl, Methoxycarbonyl, Ethoxycarbonyl, n- oder i-Propoxycarbonyl substituiert sind) substituiertes, monocyclisches Heteroaryl mit bis zu 5 Kohlenstoffatomen und mindestens einem Heteroatom aus der Reihe N (Stickstoff, 1 bis 4 N-Atome), O (Sauerstoff, 1 O-Atom), Schwefel (1 S-Atom) und gegebenenfalls ersatzweise oder zusätzlich einer SO- oder SO2- Gruppierung, und gegebenenfalls zusätzlich einer Carbonyl-Gruppierung (C=O) und/oder einer Thiocarbonyl-Gruppierung (C=S) als Bestandteil des Heterocyclus steht, odermethylthio, cyclobutylmethylthio, cyclopentylmethylthio, methylamino, ethylamino, n- or i-propylamino, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylamino, diethylamino, dimethylaminocarbonyl, diethylaminocarbonyl, acetylamino, propionylamino, n- or i-butyroylamino, methoxycarbonylamino , Ethoxycarbonylamino, n- or i-propoxycarbonylamino, methylaminocarbonylamino, ethylaminocarbonylamino, n- or i-propylaminocarbonylamino, or by phenyl, phenyloxy, benzyl, benzyloxy, phenylamino, benzylamino (where in each case the phenyl groups are optionally substituted by nitro, hydroxy, mercapto, amino , Cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, fluoroethoxy, difluoroethoxy, Trifluoroethoxy, propenyloxy, butenyloxy, propynyloxy, butynyloxy, propynylthio, butynylthio, methylsulfmyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methoxycarbonyl, ethoxycarbonyl, substituted mono- or i-propoxycarbonyl) substituted, monocyclic heteroaryl having up to 5 carbon atoms and at least one heteroatom from the series N (nitrogen, 1 to 4 N atoms), O (oxygen, 1 O atom), sulfur (1 S atom) and optionally substituted or additionally an SO or SO 2 - grouping, and optionally additionally a carbonyl group (C = O) and / or a thiocarbonyl group (C = S) as part of the heterocycle, or
R für eine der GruppierungenR for one of the groupings
steht, worinstands in which
M für Sauerstoff oder NOR7 steht,M is oxygen or NOR 7 ,
R7 für Wasserstoff; C]-C6AIlCyI, C3-C6Cycloalkyl, Ci-C4Alkylcarbonyl, C2-C4Alkenyl, C2-C4Alkynyl, Aryl, heterocyclyl oder Benzyl, steht wobei Alkyl, CycloAlkyl, Alkenyl und Alkynyl Reste unsubstituiert sind oder gegebenenfalls ein- bis fünffach mit einem Rest aus der folgender Gruppe substituiert sind: Halogen,-N3, CN, NO2, OH, SH, C-C4AIkOXy, C1-C4HaIOaIkOXy, Q-CψAlkenyloxy, C2-C4HaIo- alkenyloxy, Cs-CψAlkynyloxy, C3-C4Haloalkynyloxy, C3-C6Cycloalkyl-Cr - J -R 7 is hydrogen; C] -C6 AIlCyI, C 3 -C 6 cycloalkyl, C 4 alkylcarbonyl, C 2 -C 4 alkenyl, C 2 -C4Alkynyl, aryl, heterocyclyl or benzyl, wherein 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, CC 4 AIkOXy, C 1 -C 4 haloalkoxy, Q-CψAlkenyloxy, C 2 -C 4 Haloalkenyloxy, Cs-Cψalkynyloxy, C 3 -C 4 haloalkynyloxy, C 3 -C 6 cycloalkyl-C r - J -
C4AIkOXy, Ci-C4Halkylcarbonyl, C]-C4Haloalkylcarbonyl, Ci-C4Alkoxycarbonyl, Ci-C4Alkylcarbonyl-CrC4Alkyl> Ci-C4Alkoxycarbonyl-CrC4Alkyl, Cr QAlkylthio, C2-C4Alkylthio, C3-C4Alkynylthio, CrC4Cycloalkyl- CrC4Alkylthio, C3-C4Haloalkynyl, C2-C4Haloalkenylthio, CrC4Haloalkylthio, CrC4Alkoxy-Cr C4Alkyl, CrC4Haloalkoxy-Ci-C4Alkyl, C2-C4Alkenyloxy-C,-C4Alkyl, C2-C 4 -alkoxy, Ci-C4Halkylcarbonyl, C] -C 4 haloalkylcarbonyl, Ci-C4-alkoxycarbonyl, Ci-C4-alkylcarbonyl -C 4 alkyl> Ci-C4 alkoxycarbonyl-CrC 4 alkyl, C r QAlkylthio, C 2 -C 4 Alkylthio, C 3 -C 4 alkynylthio, C r C 4 cycloalkyl C r C 4 alkylthio, C 3 -C 4 haloalkynyl, C 2 -C 4 haloalkenylthio, C r C 4 haloalkylthio, C r C 4 alkoxy C r C 4 alkyl, -C 4 haloalkoxy-Ci-C 4 alkyl, C 2 -C 4 alkenyloxy-C, -C 4 alkyl, C 2 -
C4Haloalkenyloxy-CrC4Alkyl, C3-C4Alkynyloxy-Ci-C4Alkyl, NH2, NHC2- C4Alkenyl, C2-C4Haloalkenyl, Gs-CeAlkynyl, C3-C6Cycloalkyl, C3-C6Cycloalkyl- CrC4Alkyl, Ci-CaAlkoxy, CrC4Haloalkoxy, C2-C4Alkenyloxy, C2- C4Haloalkenyloxy, C3-C4Alkynyloxy, C3-C4Haloalkynyloxy, C3-C6Cycloalkyl-Cr C4Alkoxy, Ci-C4Alkylcarbonyl, Ci-C4Haloalkyl- Carbonyl, Ci-C4Alkoxycarbonyl,C 4 haloalkenyloxyC r C 4 alkyl, C 3 -C 4 alkynyloxy-Ci-C 4 alkyl, NH 2 , NHC 2 - C 4 alkenyl, C 2 -C 4 haloalkenyl, Gs-CeAlkynyl, C 3 -C 6 cycloalkyl , C 3 -C 6 cycloalkyl C r C 4 -alkyl, C a alkoxy, C r C 4 haloalkoxy, C 2 -C 4 alkenyloxy, C 2 - C 4 haloalkenyloxy, C 3 -C 4 alkynyloxy, C 3 - C 4 Haloalkynyloxy, C 3 -C 6 cycloalkyl-Cr C4-alkoxy, Ci-C4-alkylcarbonyl, Ci-C 4 haloalkyl carbonyl, Ci-C4-alkoxycarbonyl,
CrC4Alkylcarbonyl-Ci-C4Alkyl, CrC4Alkoxycarbonyl- CrC4Alkyl, C,- C4Alkylthio, C2-C4Alkenylthio, C3-C4Alkynylthio, C3-C6Cycloalkyl-Cr QAlkylthio, C3-C4Haloalkynyl, C2-C4Haloalkenylthio, CrC4Haloalkylthio, Cr C4AIkOXy-C1-C6AIlCyI, CrC4Haloalkoxy-Ci-C4Alkyl, C2-C4Alkenyloxy-Cr C4Alkyl, C2-C4Haloalkenyloxy-CrC4Alkyl, C3-C4Alkynyloxy-CrC4Alkyl, N(C,-C r C 4 alkylcarbonyl-Ci-C 4 alkyl, C r C 4 alkoxycarbonyl C r C 4 alkyl, C, - C 4 alkylthio, C 2 -C 4 alkenylthio, C 3 -C 4 alkynylthio, C 3 -C 6 cycloalkyl-C r QAlkylthio, C 3 -C 4 haloalkynyl, C 2 -C 4 Haloalkenylthio, C r C 4 haloalkylthio, C r C 4 -alkoxy-C 1 -C 6 AIlCyI, C r C 4 haloalkoxy-Ci-C 4 alkyl , C 2 -C 4 alkenyloxyC r C 4 alkyl, C 2 -C 4 haloalkenyloxyC r C 4 alkyl, C 3 -C 4 alkynyloxyC r C 4 alkyl, N (C, -
C4Alkyl)2, wobei die zwei Alkylgruppen unabhängig voneinander C\- C4Alkylcarbonylamino, Ci-C4Haloalkylcarbonylamino, Ci-C4-Alkoxy- carbonylamino und Ci-CφAlkylaminocarbonylamino sein können, steht,C 4 alkyl) 2 , where the two alkyl groups can be, independently of one another, C 1 -C 4 -alkylcarbonylamino, C 1 -C 4 -alkylcarbonylamino, C 1 -C 4 -alkoxycarbonylamino and C 1 -C 4 -alkylaminocarbonylamino,
R8 für Wasserstoff, Halogen, Halo(CrC4)Alkyl oder Nitro steht,R 8 is hydrogen, halogen, halo (C r C 4 ) alkyl or nitro,
n für Werte von 0 bis 2 steht,n stands for values from 0 to 2,
R10 und R11 zusammengenommen für =0 oder allein für Wasserstoff stehen undR 10 and R 11 taken together are = 0 or stand alone for hydrogen and
W für C(R32R33), wobei R32R33 jeweils unabhängig voneinander für Halogen oder Ci- QAlkyl steht.W is C (R 32 R 33 ), where R 32 R 33 are each independently halogen or C 1-10 alkyl.
3. Verbindungen der Formel (I) gemäß Anspruch 1 , gekennzeichnet dadurch dass3. Compounds of formula (I) according to claim 1, characterized in that
A1 für eine der folgenden Gruppierungen:A 1 for one of the following groupings:
-CH2-CH=CCl2, -CH2-CH=CBr2, -CH2-CH=CBrCl steht,-CH 2 -CH = CCl 2 , -CH 2 -CH = CBr 2 , -CH 2 -CH = CBrCl,
A2-X für ein geradkettiges oder verzweigtes Alkandiyl oder Alkendiyl mit jeweils bis zu 8 Kohlenstoffatomen, welches gegebenenfalls innerhalb der Kohlenstoffkette durch ein Sauerstoffatom unterbrochen sein kann, oder - D -A 2 -X represents a straight-chain or branched alkanediyl or alkenediyl each having up to 8 carbon atoms, which may optionally be interrupted by an oxygen atom within the carbon chain, or - D -
A2-X für -(C1-C4-AIlCyI)-(CO)-O-, -(C,-C4-Alkyl)-(CO)-(NH)-, -(C,-C4-Alkyl)-(CO)-[N- (C1-C4-AIlCyI)]-, -(Ci-C4-Alkyl)-(CO)-S-, (C2-C8-Alkenyl)-(CO)-O-, -(C2-C8- Alkenyl)-(CO)-(NH)-, -(C2-C8-Alkenyl)-(CO)-[N-(C1-C4-Alkyl)]-, -(C2-C8- Alkenyl)-(CO)-S, Piperidyl oder Piperazinyl, -(CrC4-Alkyl)-O-N=C(R9)-, -(C1-C6- Alkenyl)-O-N=C(CH3)- steht,A 2 -X - (C 1 -C 4 -alkyl) - (CO) -O-, - (C, -C 4 alkyl) - (CO) - (NH) -, - (C, -C 4 alkyl) - (CO) - [N- (C 1 -C 4 -alkyl)] -, - (Ci-C 4 alkyl) - (CO) -S-, (C 2 -C 8 alkenyl) - (CO) -O-, - (C 2 -C 8 alkenyl) - (CO) - (NH) -, (C 2 -C 8 alkenyl) - (CO) - [N- (C 1 -C 4- alkyl)] -, - (C 2 -C 8 alkenyl) - (CO) -S, piperidyl or piperazinyl, - (C r C 4 alkyl) -ON = C (R 9 ) -, - (C 1 -C 6 alkenyl) -ON = C (CH 3 ) -,
R.9 für Methyl oder Aryl steht, undR. 9 is methyl or aryl, and
wobei sich zwischen X und R6 gegebenenfalls das verbrückende Elementwhere between X and R 6 optionally the bridging element
befindet,is,
R1 für Wasserstoff, Nitro, Hydroxy, Cyano, Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-Propyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio, Ethylthio, n- oder i-Propylthio, Methylamino, Ethylamino, n- oder i-Propylamino oder Dimethyl- amino steht,R 1 is 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,
R2 für Wasserstoff, Nitro, Cyano, Cyanato, Thiocyanato, Formyl, Fluor, Chlor, Brom, Iod, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Methoxy, Ethoxy, n- oder i-Propoxy substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Methoxy, Ethoxy, n- oder i-Propoxy, n-, i-, s- oder t-Butoxy, Methylthio, Ethylthio, n- oder i-Propylthio, n-, i-, s- oder t-Butylthio, Methylamino, Ethylamino, n- oder i-Propylamino, n-, i-, s- oder t-Butylamino, Dimethylamino, Diethylamino, Acetylamino, Propionylamino, n- oder i-Butyroylamino, Acetyl, Propionyl, n- oder i-Butyroyl, Methoxycarbonyl, Ethoxycarbonyl, n-oder i-Propoxycarbonyl, Methoximinoformyl, Ethoximinoformyl, Methoximinoacetyl oder Ethoximino- acetyl steht,R 2 is hydrogen, nitro, cyano, cyanato, thiocyanato, formyl, 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, dimethylamino, diethylamino, acetylamino, propionylamino, n- or i-butyroylamino, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methoximinoformyl, ethoximinoformyl, methoximinoacetyl or ethoximinoacetyl,
R3 für Wasserstoff, Nitro, Fluor, Chlor, Brom, Iod, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Methoxy, Ethoxy, n- oder i-Propoxy substituiertes Methyl,R 3 is hydrogen, nitro, fluorine, chlorine, bromine, iodine, in each case optionally cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy-substituted methyl,
Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Methoxy, Ethoxy, n- oder i-Propoxy, n-, i-, s- oder t-Butoxy, Methylthio, Ethylthio, n- oder i-Propylthio, n-, i-, s- oder t- Butylthio, Methylamino, Ethylamino, n- oder i-Propylamino, n-, i-, s- oder t-Butyl- amino steht, R4 für Wasserstoff, Nitro, Fluor, Chlor, Brom, Iod, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Methoxy, Ethoxy, n- oder i-Propoxy substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Methoxy, Ethoxy, n- oder i-Propoxy, n-, i-, s- oder t-Butoxy, Methylthio, Ethylthio, n- oder i-Propylthio, n-, i-, s- oder t- Butylthio, Methylamino, Ethylamino, n- oder i-Propylamino, n-, i-, s- oder t-Butyl- amino steht,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 is 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-butyl-amino,
R5 für Wasserstoff, Methyl, i-Propyl, Cyclopropy oder Cyclohexyl steht,R 5 is hydrogen, methyl, i-propyl, cyclopropyl or cyclohexyl,
R6 für eine der GruppierungenR 6 for one of the groupings
steht, worinstands in which
A3 für eine Einfachbindung oder für jeweils gegebenenfalls durch Fluor, Chlor, Brom,A 3 represents a single bond or optionally in each case by fluorine, chlorine, bromine,
Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl substituiertes Methylen,Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl substituted methylene,
Ethan-l,l-diyl (Ethyliden), Ethan-l,2-diyl (Dimethylen), Propan-l,l-diylEthane-1, l-diyl (ethylidene), ethane-l, 2-diyl (dimethylene), propane-l, l-diyl
(Propyliden), Propan-l,2-diyl, Propan-l,3-diyl (Trimethylen), Butan- 1,1-diyl (Butyliden) oder Butan-1 ,4-diyl (Tetramethylen) steht,(Propylidene), propan-l, 2-diyl, propane-l, 3-diyl (trimethylene), butane-1,1-diyl (butylidene) or butane-1, 4-diyl (tetramethylene),
M für Sauerstoff steht,M stands for oxygen,
W für C(R32R33), wobei R32R33 jeweils unabhängig voneinander für Halogen oder Methyl steht,W is C (R 32 R 33 ), where R 32 R 33 is each independently halogen or methyl,
Z für jeweils gegebenenfalls durch Nitro, Hydroxy, Amino, Formyl, Cyano, Carboxy, Carbamoyl, Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Fluormethyl, Chlormethyl, Difiuormethyl, Dichlormethyl, Trifluor- methyl, Trichlormethyl, Fluorethyl, Chlorethyl, Difluorethyl, Dichlorethyl,Z is 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, trichloromethyl, fluoroethyl, chloroethyl, difluoroethyl, dichloroethyl,
Chlorfluorethyl, Trifluorethyl, Trichlorethyl, Chlordifluorethyl, Fluoφropyl,Chlorofluoroethyl, trifluoroethyl, trichloroethyl, chlorodifluoroethyl, fluoφropyl,
Chlorpropyl, Difluorpropyl, Dichloφropyl, Trifluorpropyl, Fluor-i-propyl, Difluor-i-propyl, Trifluor-i-propyl, Tetrafluor-i-propyl, Pentafluor-i-propyl,Chloropropyl, difluoropropyl, dichloφropyl, trifluoropropyl, fluoro-i-propyl, difluoro-i-propyl, trifluoro-i-propyl, tetrafluoro-i-propyl, pentafluoro-i-propyl,
Methoxy, Ethoxy, n- oder i-Propoxy, Fluormethoxy, Difluormethoxy,Methoxy, ethoxy, n- or i-propoxy, fluoromethoxy, difluoromethoxy,
Trifluormethoxy, Fluordichlormethoxy, Chlordifluormethoxy, Fluorethoxy,Trifluoromethoxy, fluorodichloromethoxy, chlorodifluoromethoxy, fluoroethoxy,
Chlorethoxy, Difluorethoxy, Dichlorethoxy, Trifluorethoxy, Fluoφropoxy, - -Chloroethoxy, difluoroethoxy, dichloroethoxy, trifluoroethoxy, fluoφropoxy, - -
Methoxycarbonyl, Ethoxycarbonyl, Fluorethoxycarbonyl, Chlorethoxycarbonyl, Methoxymethyl, Ethoxymethyl, n- oder i-Propoxymethyl, Methoxyethyl, Ethoxy- ethyl, n- oder i-Propoxyethyl, Ethenyl, Propenyl, Butenyl, Fluorethenyl, Chlor- ethenyl, Difluorethenyl, Dichlorethenyl, Trifluorethenyl, Trichlorethenyl, Prope- nyloxymethyl, Butenyloxymethyl, Propenyloxyethyl, Butenyloxyethyl, Ethinyl,Methoxycarbonyl, ethoxycarbonyl, fluoroethoxycarbonyl, chloroethoxycarbonyl, methoxymethyl, ethoxymethyl, n- or i-propoxymethyl, methoxyethyl, ethoxyethyl, n- or i-propoxyethyl, ethenyl, propenyl, butenyl, fluoroethenyl, chloroethenyl, difluoroethenyl, dichloroethenyl, trifluoroethenyl, Trichloroethenyl, propenyloxymethyl, butenyloxymethyl, propenyloxyethyl, butenyloxyethyl, ethynyl,
Propinyl, Butinyl, Propenyloxy, Butenyloxy, Fluorpropenyloxy, Chlorpropenyl- oxy, Fluorbutenyloxy, Chlorbutenyloxy, Propenyloxycarbonyl, Butenyloxy- carbonyl, Propinyloxy, Butinyloxy, Propinyloxycarbonyl, Butinyloxycarbonyl, Propinyloxymethyl, Butinyloxymethyl, Propinyloxyethyl, Butinyloxyethyl, Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclopropylcarbonyl, Cyclobutylcarbonyl,Propinyl, butinyl, propenyloxy, butenyloxy, fluoropropenyloxy, chloropropenyl-oxy, fluorobutenyloxy, chlorobutenyloxy, propenyloxycarbonyl, butenyloxycarbonyl, propynyloxy, butynyloxy, propynyloxycarbonyl, butynyloxycarbonyl, propynyloxymethyl, butynyloxymethyl, propynyloxyethyl, butynyloxyethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclopropylcarbonyl, cyclobutylcarbonyl,
Cyclopentylcarbonyl, Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl, Cyclohexylmethyl, Cyclopropylmethylcarbonyl, Cyclobutylmethylcarbonyl, Cyclopentylmethylcarbonyl, Cyclopropyloxy, Cyclobutyloxy, Cyclopentyloxy, Cyclohexyloxy, Cyclopropyloxycarbonyl, Cyclobutyloxycarbonyl, Cyclopentyl- oxycarbonyl, Cyclohexyloxycarbonyl, Cyclopropylmethoxy, Cyclobutylmethoxy,Cyclopentylcarbonyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethylcarbonyl, cyclobutylmethylcarbonyl, cyclopentylmethylcarbonyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropyloxycarbonyl, cyclobutyloxycarbonyl, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl, cyclopropylmethoxy, cyclobutylmethoxy,
Cyclopentylmethoxy, Cyclohexylmethoxy, Cyclopropylmethoxycarbonyl, Cyclobutylmethoxycarbonyl, Cyclopentylmethoxycarbonyl,Cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethoxycarbonyl, cyclobutylmethoxycarbonyl, cyclopentylmethoxycarbonyl,
Cyclohexylmethoxycarbonyl, Cyclopropylmethoxymethyl, Cyclo- butylmethoxymethyl, Cyclopentylmethoxymethyl, Cyclopropyloxymethoxy, Cyclobutyloxymethoxy, Cyclopentyloxymethoxy, Acetylmethyl, Propionylmethyl, n- oder i-Butyroylmethyl, Acetylethyl, Propionylethyl, Methoxycarbonylmethyl, Ethoxycarbonylmethyl, n- oder i-Propoxycarbonylmethyl, Methoxycarbonylethyl, Ethoxycarbonylethyl, n- oder i-Propoxycarbonylethyl, Methylthio, Ethylthio, n- oder i-Propylthio, Difluormethylthio, Trifluormethylthio, Chlordifluormethylthio, Methylsulfinyl, Ethylsulfinyl, Trifluormethylsulfinyl, Methylsulfonyl, Ethyl- sulfonyl, Trifluormethylsulfonyl, Propenylthio, Butenylthio, Fluoφropenylthio, Chlorpropenylthio, Fluorbutenylthio, Chlorbutenylthio, Propinylthio, Butinylthio, Cyclopropylthio, Cyclobutylthio, Cyclopentylthio, Cyclohexylthio, Cyclopropyl- methylthio, Cyclobutylmethylthio, Cyclopentylmethylthio, Methylamino, Ethyl- amino, n- oder i-Propylamino, Methylaminocarbonyl, Ethylaminocarbonyl, n- oder i-Propylaminocarbonyl, Dimethylamino, Diethylamino, Dimethylaminocarbonyl, Diethylaminocarbonyl, Acetylamino, Propionylamino, n- oder i-Butyroylamino, Methoxycarbonylamino, Ethoxycarbonylamino, n- oder i-Propoxycarbonylamino, Methylaminocarbonylamino, Ethylaminocarbonylamino, n- oder i-Propylamino- carbonylamino, oder durch Phenyl, Phenyloxy, Benzyl, Benzyloxy, Phenylamino,Cyclohexylmethoxycarbonyl, cyclopropylmethoxymethyl, cyclobutylmethoxymethyl, cyclopentylmethoxymethyl, cyclopropyloxymethoxy, cyclobutyloxymethoxy, cyclopentyloxymethoxy, acetylmethyl, propionylmethyl, n- or i-butyroylmethyl, acetylethyl, propionylethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, n- or i-propoxycarbonylmethyl, methoxycarbonylethyl, ethoxycarbonylethyl, n- or i -Propoxycarbonylethyl, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, methylsulfinyl, ethylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, trifluoromethylsulfonyl, propenylthio, butenylthio, fluoφropenylthio, chloropropenylthio, fluorobutenylthio, chlorobutenylthio, propynylthio, butynylthio, Cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylmethylthio, cyclobutylmethylthio, cyclopentylmethylthio, methylamino, ethylamino, n- or i-propylamino, methylaminocarbonyl, ethylaminocarbonyl, n- or i-pr opylaminocarbonyl, dimethylamino, diethylamino, dimethylaminocarbonyl, diethylaminocarbonyl, acetylamino, propionylamino, n- or i-butyroylamino, methoxycarbonylamino, ethoxycarbonylamino, n- or i-propoxycarbonylamino, methylaminocarbonylamino, ethylaminocarbonylamino, n- or i-propylaminocarbonylamino, or by phenyl, phenyloxy , Benzyl, benzyloxy, phenylamino,
Benzylamino (wobei jeweils die Phenylgruppen gegebenenfalls durch Nitro, Hydroxy, Mercapto, Amino, Cyano, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Trifluormethyl, Methoxy, Ethoxy, n- oder i-Propoxy, Difluormethoxy, Trifluormethoxy, Fluorethoxy, Difluorethoxy, Trifluorethoxy, Propenyloxy, Butenyloxy, Propinyloxy, Butinyloxy, Propinylthio, Butinylthio, Methylsulfϊnyl, Ethylsulfinyl, Methylsulfonyl, Ethylsulfonyl, Methoxycarbonyl, Ethoxycarbonyl, n- oder i-Propoxycarbonyl substituiert sind) substituiertes Pyrrolyl, Pyrazolyl, Imidazolyl, Triazolyl, Tetrazolyl, Furyl, Thienyl, Oxazolyl, Isoxazolyl, Thiazolyl, Isothiazolyl, Oxadiazolyl, Thiadiazolyl, Pyridinyl, Pyrimidinyl, Pyridazinyl, Pyrazinyl steht.Benzylamino (where each of the phenyl groups is optionally substituted by nitro, Hydroxy, mercapto, amino, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, fluoroethoxy , Difluoroethoxy, trifluoroethoxy, propenyloxy, butenyloxy, propynyloxy, butynyloxy, propynylthio, butynylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl) substituted pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, furyl , Thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl.
4. Verbindungen der Formel (I) gemäß Anspruch 1, dadurch gekennzeichnet, dass,4. Compounds of formula (I) according to claim 1, characterized in that,
A1 für die Gruppierung -CH2-CH=CCl2 steht,A 1 represents the group -CH 2 -CH = CCl 2 ,
A2-X für ein geradkettiges oder verzweigtes Alkandiyl mit bis zu 8 Kohlenstoffatomen, welches gegebenenfalls innerhalb der Kohlenstoffkette ein Sauerstoffatom enthält sowie für -(CrC4-Alkyl)-(CO)-O-, -(Ci-C4-Alkyl)-(CO)-(NH)- oder Piperidyl steht,A 2 -X is 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-, - (Ci-C 4 - Alkyl) - (CO) - (NH) - or piperidyl,
R1 für Wasserstoff, Methyl, Ethyl, Methoxy, Ethoxy oder Fluor, Chlor, Brom steht,R 1 is hydrogen, methyl, ethyl, methoxy, ethoxy or fluorine, chlorine, bromine,
R2 für Wasserstoff, Cyano, Fluor, Chlor, Brom oder Iod steht,R 2 is hydrogen, cyano, fluorine, chlorine, bromine or iodine,
R2 für Wasserstoff, Fluor, Chlor oder Brom steht,R 2 is hydrogen, fluorine, chlorine or bromine,
R3 für Wasserstoff, Cyano, Fluor, Chlor, Brom, Methyl, Ethyl, Methoxy oder Ethoxy steht,R 3 is hydrogen, cyano, fluorine, chlorine, bromine, methyl, ethyl, methoxy or ethoxy,
R4 für Wasserstoff, Cyano, Fluor, Chlor oder Brom steht,R 4 is hydrogen, cyano, fluorine, chlorine or bromine,
R5 für Methyl steht,R 5 is methyl,
R6 für eine GruppierungR 6 for a grouping
steht, worin A3 für eine Einfachbindung oder für Methylen steht undstands in which A 3 is a single bond or methylene and
Z für jeweils gegebenenfalls durch Nitro, Hydroxy, Amino, Formyl, Cyano, Carboxy, Carbamoyl, Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Fluormethyl, Chlormethyl, Difluormethyl, Dichlormethyl, Trifluor- methyl, Trichlormethyl, Fluorethyl, Chlorethyl, Difiuorethyl, Dichlorethyl,Z is 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, trichloromethyl, fluoroethyl, chloroethyl, difluoroethyl, dichloroethyl,
Chlorfluorethyl, Trifluorethyl, Trichlorethyl, Chlordifluorethyl, Fluoφropyl, Chloφropyl, Difluoφropyl, Dichloφropyl, Trifluoφropyl, Fluor-i-propyl, Difluor-i-propyl, Trifluor-i-propyl, Tetrafluor-i-propyl, Pentafluor-i-propyl, Methoxy, Ethoxy, n- oder i-Propoxy, Fluormethoxy, Difluormethoxy, Trifluormethoxy, Fluordichlormethoxy, Chlordifluormethoxy, Fluorethoxy,Chlorofluoroethyl, trifluoroethyl, trichloroethyl, chlorodifluoroethyl, fluoφropyl, chloφropyl, difluoropropyl, dichloφropyl, trifluoropropyl, fluoro-i-propyl, difluoro-i-propyl, trifluoro-i-propyl, tetrafluoro-i-propyl, pentafluoro-i-propyl, methoxy, Ethoxy, n- or i-propoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, fluorodichloromethoxy, chlorodifluoromethoxy, fluoroethoxy,
Chlorethoxy, Difluorethoxy, Dichlorethoxy, Trifluorethoxy, Fluoφropoxy, Methoxycarbonyl, Ethoxycarbonyl, Fluorethoxycarbonyl, Chlorethoxycarbonyl, Methoxymethyl, Ethoxymethyl, n- oder i-Propoxymethyl, Methoxyethyl, Ethoxy- ethyl, n- oder i-Propoxyethyl, Ethenyl, Propenyl, Butenyl, Fluorethenyl, Chlor- ethenyl, Difluorethenyl, Dichlorethenyl, Trifluorethenyl, Trichlorethenyl, Prope- nyloxymethyl, Butenyloxymethyl, Propenyloxyethyl, Butenyloxyethyl, Ethinyl, Propinyl, Butinyl, Propenyloxy, Butenyloxy, Fluoφropenyloxy, Chloφropenyl- oxy, Fluorbutenyloxy, Chlorbutenyloxy, Propenyloxycarbonyl, Butenyloxy- carbonyl, Propinyloxy, Butinyloxy, Propinyloxycarbonyl, Butinyloxycarbonyl, Propinyloxymethyl, Butinyloxymethyl, Propinyloxyethyl, Butinyloxyethyl,Chloroethoxy, difluoroethoxy, dichloroethoxy, trifluoroethoxy, fluoφropoxy, methoxycarbonyl, ethoxycarbonyl, fluoroethoxycarbonyl, chloroethoxycarbonyl, methoxymethyl, ethoxymethyl, n- or i-propoxymethyl, methoxyethyl, ethoxyethyl, n- or i-propoxyethyl, ethenyl, propenyl, butenyl, fluoroethenyl, Chloroethenyl, difluoroethenyl, dichloroethenyl, trifluoroethenyl, trichloroethenyl, propenyloxymethyl, butenyloxymethyl, propenyloxyethyl, butenyloxyethyl, ethynyl, propynyl, butynyl, propenyloxy, butenyloxy, fluoφropenyloxy, chloφrophenyloxy, fluorobutenyloxy, chlorobutenyloxy, propenyloxycarbonyl, butenyloxycarbonyl, propynyloxy, Butinyloxy, propinyloxycarbonyl, butinyloxycarbonyl, propinyloxymethyl, butinyloxymethyl, propinyloxyethyl, butynyloxyethyl,
Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclopropylcarbonyl, Cyclobutylcarbonyl, Cyclopentylcarbonyl, Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl, Cyclohexylmethyl, Cyclopropyhnethylcarbonyl, Cyclobutylmethylcarbonyl, Cyclopentylmethylcarbonyl, Cyclopropyloxy, Cyclobutyloxy, Cyclopentyloxy, Cyclohexyloxy, Cyclopropyloxycarbonyl, Cyclobutyloxycarbonyl, Cyclopentyl- oxycarbonyl, Cyclohexyloxycarbonyl, Cyclopropylmethoxy, Cyclobutylmethoxy, Cyclopentylmethoxy, Cyclohexylmethoxy, Cyclopropylmethoxycarbonyl, Cyclobutyhnethoxycarbonyl, Cyclopentylmethoxycarbonyl,Cyclopropyl, cyclobutyl, cyclopentyl, cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, Cyclopropyhnethylcarbonyl, Cyclobutylmethylcarbonyl, Cyclopentylmethylcarbonyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropyloxycarbonyl, cyclobutyloxycarbonyl, cyclopentyl oxycarbonyl, cyclohexyloxycarbonyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, Cyclohexylmethoxy, cyclopropylmethoxycarbonyl, cyclobutyhnethoxycarbonyl, cyclopentylmethoxycarbonyl,
Cyclohexylmethoxycarbonyl, Cyclopropylmethoxymethyl, Cyclo- butylmethoxymethyl, Cyclopentylmethoxymethyl, Cyclopropyloxymethoxy,Cyclohexylmethoxycarbonyl, cyclopropylmethoxymethyl, cyclobutylmethoxymethyl, cyclopentylmethoxymethyl, cyclopropyloxymethoxy,
Cyclobutyloxymethoxy, Cyclopentyloxymethoxy, Acetylmethyl, Propionylmethyl, n- oder i-Butyroylmethyl, Acetylethyl, Propionylethyl, Methoxycarbonylmethyl, Ethoxycarbonylmethyl, n- oder i-Propoxycarbonylmethyl, Methoxycarbonylethyl, Ethoxycarbonylethyl, n- oder i-Propoxycarbonylethyl, Methylthio, Ethylthio, n- oder i-Propylthio, Difluormethylthio, Trifluormethylthio, Chlordifluormethylthio, Methylsulfinyl, Ethylsulfinyl, Trifluormethylsulfinyl, Methylsulfonyl, Ethyl- sulfonyl, Trifluormethylsulfonyl, Propenylthio, Butenylthio, Fluoφropenylthio, Chloφropenylthio, Fluorbutenylthio, Chlorbutenylthio, Propinylthio, Butinylthio, Cyclopropylthio, Cyclobutylthio, Cyclopentylthio, Cyclohexylthio, Cyclopropyl- methylthio, Cyclobutylmethylthio, Cyclopentylmethylthio, Methylamino, Ethyl- amino, n- oder i-Propylamino, Methylaminocarbonyl, Ethylaminocarbonyl, n- oder i-Propylaminocarbonyl, Dimethylamino, Diethylamino, Dimethylaminocarbonyl, Diethylaminocarbonyl, Acetylamino, Propionylamino, n- oder i-Butyroylamino, Methoxycarbonylamino, Ethoxycarbonylamino, n- oder i-Propoxycarbonylamino, Methylaminocarbonylamino, Ethylaminocarbonylamino, n- oder i-Propylamino- carbonylamino, oder durch Phenyl, Phenyloxy, Benzyl, Benzyloxy, Phenylamino, Benzylamino (wobei jeweils die Phenylgruppen gegebenenfalls durch Nitro, Hydroxy, Mercapto, Amino, Cyano, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Trifluormethyl, Methoxy, Ethoxy, n- oder i-Propoxy, Difluormethoxy, Trifluormethoxy, Fluorethoxy, Difluorethoxy, Trifluorethoxy, Propenyloxy,Cyclobutyloxymethoxy, cyclopentyloxymethoxy, acetylmethyl, propionylmethyl, n- or i-butyroylmethyl, acetylethyl, propionylethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, n- or i-propoxycarbonylmethyl, methoxycarbonylethyl, ethoxycarbonylethyl, n- or i-propoxycarbonylethyl, methylthio, ethylthio, n- or i- Propylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, Methylsulfinyl, ethylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethyl sulfonyl, trifluoromethylsulfonyl, propenylthio, butenylthio, Fluoφropenylthio, Chloφropenylthio, Fluorbutenylthio, Chlorbutenylthio, propynylthio, butynylthio, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropyl methylthio, Cyclobutylmethylthio, Cyclopentylmethylthio, methylamino, ethyl amino, n- or i-propylamino, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylamino, diethylamino, dimethylaminocarbonyl, diethylaminocarbonyl, acetylamino, propionylamino, n- or i-butyroylamino, methoxycarbonylamino, ethoxycarbonylamino, n- or i-propoxycarbonylamino, Methylaminocarbonylamino, ethylaminocarbonylamino, n- or i-propylaminocarbonylamino, or by phenyl, phenyloxy, benzyl, benzyloxy, phenylamino, benzylamino (where in each case the phenyl groups are optionally substituted by nitro, hydroxy, mercapto, amino, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, fluoroethoxy, difluoroethoxy, trifluoroethoxy, propenyloxy,
Butenyloxy, Propinyloxy, Butinyloxy, Propinylthio, Butinylthio, Methylsulfinyl, Ethylsulfinyl, Methylsulfonyl, Ethylsulfonyl, Methoxycarbonyl, Ethoxycarbonyl, n- oder i-Propoxycarbonyl substituiert sind)substituiertes Tetrazolyl steht.Butenyloxy, propinyloxy, butynyloxy, propynylthio, butynylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl) substituted tetrazolyl.
5. Verfahren zur Herstellung von Verbindungen der allgemeinen Formel (I) gemäß Anspruch 1 , durch Umsetzung von Verbindungen der allgemeinen Formel (II),5. A process for preparing compounds of general formula (I) according to claim 1, by reacting compounds of general formula (II),
mit Verbindungen der allgemeinen Formel H2N-O- A2-X-R6, wobei die Reste wobei die Reste R1, R2, R3, A1, R4, R5, A2, X und R6 die in Anspruch 1 angegebenen Bedeutungen haben oder durch Umsetzung von Verbindungen der allgemeinen Formel (IV) - - with compounds of the general formula H 2 NO-A 2 -XR 6 , where the radicals where R 1 , R 2 , R 3 , A 1 , R 4 , R 5 , A 2 , X and R 6 are as defined in claim 1 have specified meanings or by reaction of compounds of general formula (IV) - -
mit einer Verbindung der allgemeinen Formel ausgewählt aus: LG-R6, HO-R6, H2N-R6 oder LG-CO-R6, wobei die Reste R1, R2, R3, A1, R4, R5, A2, X und R6 die in Anspruch 1 angegebene Bedeutung haben und LG für eine Abgangsgruppe steht. with a compound of the general formula selected from: LG-R 6 , HO-R 6 , H 2 NR 6 or LG-CO-R 6 , where the radicals R 1 , R 2 , R 3 , A 1 , R 4 , R 5 , A 2 , X and R 6 have the meaning given in claim 1 and LG is a leaving group.
6. Mittel, gekennzeichnet durch einen Gehalt von mindestens einer Verbindung der Formel (I) gemäß Anspruch 1 und üblichen Streckmitteln und/oder oberflächenaktiven Substanzen.6. agent, characterized by a content of at least one compound of formula (I) according to claim 1 and conventional extenders and / or surface-active substances.
7. Verfahren zum Bekämpfen von Schädlingen, dadurch gekennzeichnet, dass man eine Verbindung der Formel (I) gemäß Anspruch 1 oder ein Mittel gemäß Anspruch 13 auf die Schädlinge und/oder ihren Lebensraum einwirken lässt.7. A method for controlling pests, which comprises allowing a compound of formula (I) according to claim 1 or an agent according to claim 13 to act on the pests and / or their habitat.
8. Verwendung von Verbindungen der Formel (I) gemäß Anspruch 1 oder von Mitteln gemäß Anspruch 13 zum Bekämpfen von Schädlingen. 8. Use of compounds of formula (I) according to claim 1 or of agents according to claim 13 for controlling pests.
EP06849372A 2005-05-14 2006-05-06 Substituted aryl oximes Withdrawn EP1883622A1 (en)

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