DE19531300A1 - Fluorobutenic acid amides - Google Patents

Fluorobutenic acid amides

Info

Publication number
DE19531300A1
DE19531300A1 DE19531300A DE19531300A DE19531300A1 DE 19531300 A1 DE19531300 A1 DE 19531300A1 DE 19531300 A DE19531300 A DE 19531300A DE 19531300 A DE19531300 A DE 19531300A DE 19531300 A1 DE19531300 A1 DE 19531300A1
Authority
DE
Germany
Prior art keywords
alkyl
formula
spp
halogen
optionally substituted
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Withdrawn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
DE19531300A
Other languages
German (de)
Inventor
Udo Dr Kraatz
Wolfram Dr Andersch
Ulrike Dr Wachendorff-Neumann
Andreas Dr Turnberg
Norbert Dr Mencke
Gopichand Yalamanchili
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 AG
Monsanto Co
Original Assignee
Bayer AG
Monsanto Co
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 AG, Monsanto Co filed Critical Bayer AG
Priority to DE19531300A priority Critical patent/DE19531300A1/en
Priority to CN96197624A priority patent/CN1200109A/en
Priority to CA002230100A priority patent/CA2230100A1/en
Priority to JP9509775A priority patent/JPH11511438A/en
Priority to PCT/EP1996/003570 priority patent/WO1997008132A1/en
Priority to EP96929247A priority patent/EP0848698A1/en
Priority to KR1019980701266A priority patent/KR19990044034A/en
Priority to AU68729/96A priority patent/AU6872996A/en
Priority to BR9610023A priority patent/BR9610023A/en
Priority to TR1998/00297T priority patent/TR199800297T1/en
Publication of DE19531300A1 publication Critical patent/DE19531300A1/en
Priority to MXPA/A/1998/001493A priority patent/MXPA98001493A/en
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C233/09—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an acyclic unsaturated carbon skeleton
    • 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
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/40—Acylated substituent nitrogen atom
    • 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
    • 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
    • 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
    • A01N37/24—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 containing at least one oxygen or sulfur atom being directly attached to the same aromatic ring system
    • 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
    • A01N37/44—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/10—Sulfones; Sulfoxides
    • 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
    • A01N43/08—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 with oxygen as the ring hetero atom
    • 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
    • A01N43/10—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 with sulfur as the ring hetero atom
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
    • C07C233/15—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/24—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
    • C07C233/27—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/30—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms
    • C07C233/33—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • C07C233/42—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
    • C07C233/44—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a carbon atom of an unsaturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/53—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
    • C07C233/55—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a carbon atom of an unsaturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
    • C07C255/60—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton at least one of the singly-bound nitrogen atoms being acylated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C317/34—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring
    • C07C317/38—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring with the nitrogen atom of at least one amino group being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfones
    • C07C317/40—Y being a hydrogen or a carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
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    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/14—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
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    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with 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
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/36—Nitrogen atoms
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    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/46—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings substituted on the ring sulfur atom
    • C07D333/48—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings substituted on the ring sulfur atom by oxygen atoms
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    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pyridine Compounds (AREA)
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Abstract

The present invention relates to new fluorobutene acid amides of formula (I), in which R<1 >is hydrogen or halogen; R<2> is hydrogen, alkyl or phenyl optionally substituted by halogen or alkyl; R<3> is one of the residues specified under a); b); c), wherein a methylene group is optionally replaced by SO2, or one or two not directly adjacent methylene groups are replaced by oxygen, sulphur or nitrogen (which is optionally substituted by alkyl, phenyl or benzyl); or d) 5 or 6-membered hetarylalkyl optionally substituted by alkyl or by phenyl optionally substituted by halogen, alkyl, alkyl halide, alkoxy or alkoxy halide, and one to three heteroatoms from the series of oxygen, sulphur and nitrogen; or e) is benzthiazolyl or pyridyl in each case optionally substituted by halogen, alkyl or alkyl halide, wherein X, Y, Z, R<4>, W, n, l and m have the meaning given in the description. It also relates to a method for the preparation thereof, and the use thereof for the control of animal pests.

Description

Die vorliegende Erfindung betrifft neue Fluorbutensäureamide, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von tierischen Schädlingen, insbesondere von Insekten, Spinnentieren und Nematoden, die in der Landwirt­ schaft, in Forsten, im Vorrats- und Materialschutz sowie auf dem Hygienesektor vorkommen.The present invention relates to new fluorobutenseamides, processes for their Production and their use for controlling animal pests, especially of insects, arachnids and nematodes that are in the farmer shaft, in forests, in the protection of stored goods and materials as well as in the hygiene sector occurrence.

Aus der WO 92/15 555 ist bekannt, daß die Verbindungen N-Phenyl-3,4,4-tri­ fluorbut-3-ensäureamid und N-(3-Carboxyphenyl)-3,4,4-trifluorbut-3-ensäureamid insektizide, akarizide und nematizide Eigenschaften aufweisen. Fluorvinyl­ carboxamidderivate mit insektiziden und akariziden Eigenschaften sind aus EP-A 0 661 289 bekannt.From WO 92/15 555 it is known that the compounds N-phenyl-3,4,4-tri fluorobut-3-enoamide and N- (3-carboxyphenyl) -3,4,4-trifluorobut-3-enoamide have insecticidal, acaricidal and nematicidal properties. Fluorovinyl carboxamide derivatives with insecticidal and acaricidal properties are from EP-A 0 661 289 known.

Die Wirksamkeit und Wirkungsbreite dieser Verbindungen ist jedoch insbesondere bei niedrigen Aufwandmengen und Konzentrationen nicht immer völlig zufrieden­ stellend.However, the effectiveness and range of action of these compounds is particular not always completely satisfied with low application rates and concentrations posed.

Es wurden nun neue Fluorbutensäureamide der Formel (I) gefunden,New fluorobutenamides of the formula (I) have now been found

in welcher
R¹ für Wasserstoff oder Halogen steht,
R² für Wasserstoff, Alkyl oder gegebenenfalls durch Halogen oder Alkyl substituiertes Phenyl steht,
R³ fürin which
R¹ represents hydrogen or halogen,
R² represents hydrogen, alkyl or phenyl which is optionally substituted by halogen or alkyl,
R³ for

steht worin
X für Amino, Hydroxy, Mercapto, Nitro, Cyano, Halogen, Alkyl, Halogenalkyl, Alkoxy, Halogenalkoxy, Alkylthio, Halogenalkylthio, Alkylsulfonyl, Halogenalkylsulfonyl, Al­ kylcarbonyl, Alkoxycarbonyl, Alkylamino, Dialkylamino, Aminocarbonyl, Alkylaminocarbonyl, Dialkylaminocarbonyl oder Halogenalkenylcarbonylamino steht,
Y und Z unabhängig voneinander für Wasserstoff- Amino, Hydroxy, Mercapto, Cyano, Carboxyl, Halogen, Alkyl, Halogenalkyl, Alkoxy, Halogenalkoxy, Alkylthio, Halogenalkylthio, Alkyl­ carbonyl, Alkoxycarbonyl, Alkylamino, Dialkylamino, Alkyl­ aminocarbonyl oder Dialkylaminocarbonyl stehen oderstands in what
X represents amino, hydroxy, mercapto, nitro, cyano, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfonyl, haloalkylsulfonyl, alkylcarbonyl, alkoxycarbonyl, alkylamino, dialkylamino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl or haloalkenylcarbonyl
Y and Z independently of one another represent hydrogen-amino, hydroxy, mercapto, cyano, carboxyl, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylcarbonyl, alkoxycarbonyl, alkylamino, dialkylamino, alkyl aminocarbonyl or dialkylaminocarbonyl or

steht, worin
X und Y die oben angegebene Bedeutung haben,
R⁴ für Wasserstoff oder Alkyl steht und
n für 0, 1, 2, 3 oder 4 steht oderstands in what
X and Y have the meaning given above,
R⁴ represents hydrogen or alkyl and
n stands for 0, 1, 2, 3 or 4 or

steht, worin
gegebenenfalls eine Methylengruppe durch SO₂ ersetzt ist oder eine oder zwei nicht direkt benachbarte Methylengruppen im Ring durch Sauerstoff, Schwefel oder Stickstoff (welcher gegebenenfalls durch Alkyl, Phenyl oder Benzyl substituiert ist) ersetzt sind,
1 für 0, 1 oder 2 steht,
m für 0, 1, 2, 3, 4 oder 5 steht und
W für Halogen, Alkyl oder gegebenenfalls durch Halogen, Alkyl, Halogenalkyl, Alkoxy oder Halogenalkoxy substituier­ tes Phenyl steht oderstands in what
optionally a methylene group is replaced by SO₂ or one or two not directly adjacent methylene groups in the ring are replaced by oxygen, sulfur or nitrogen (which is optionally substituted by alkyl, phenyl or benzyl),
1 represents 0, 1 or 2,
m represents 0, 1, 2, 3, 4 or 5 and
W represents halogen, alkyl or phenyl substituted by halogen, alkyl, haloalkyl, alkoxy or haloalkoxy or

d) gegebenenfalls durch Halogen, Alkyl oder durch gegebenenfalls durch Halogen, Alkyl, Halogenalkyl, Alkoxy oder Halogenalkoxy substituiertes Phenyl substituiertes 5- oder 6-gliedriges Hetarylalkyl steht mit ein bis drei Heteroatomen aus der Reihe Sauerstoff, Schwefel und Stickstoff.d) optionally by halogen, alkyl or by optionally by halogen, alkyl, haloalkyl, alkoxy or haloalkoxy substituted phenyl substituted 5- or 6-membered hetarylalkyl stands with one to three heteroatoms from the series oxygen, Sulfur and nitrogen.

Die Verbindungen der Formel (I) können in Abhängigkeit von der Art der Substi­ tuenten als geometrische und/oder optische Isomere oder Isomerengemische unter­ schiedlicher Zusammensetzung vorliegen. Die Erfindung betrifft sowohl die reinen Isomeren als auch die Isomerengemische.The compounds of formula (I) can, depending on the nature of the Substi tuenten as geometric and / or optical isomers or isomer mixtures under different composition. The invention relates to both the pure Isomers as well as the isomer mixtures.

Weiter wurde gefunden, daß man die Fluorbutensäureamide der Formel (I) erhält, wenn man
Amine der Formel (II)It has also been found that the fluorobutenamides of the formula (I) can be obtained if
Amines of formula (II)

HNR²R³ (II)HNR²R³ (II)

in welcher
R² und R³ die oben angegebene Bedeutung haben,
mit Säurechloriden der Formel (III)in which
R² and R³ have the meaning given above,
with acid chlorides of the formula (III)

in welcher
R¹ die oben angegebene Bedeutung hat,
gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Ge­ genwart einer Base umsetzt.in which
R¹ has the meaning given above,
if appropriate in the presence of a diluent and if appropriate in the presence of a base.

Schließlich wurde gefunden, daß die neuen Fluorbutensäureamide der Formel (I) stark ausgeprägte biologische Eigenschaften besitzen und vor allem zur Bekämp­ fung von tierischen Schädlingen, insbesondere von Insekten, Spinnentieren und Nematoden, die in der Landwirtschaft, in Forsten, im Vorrats- und Materialschutz sowie auf dem Hygienesektor vorkommen, geeignet sind.Finally, it was found that the new fluorobutenamides of the formula (I) have strong biological properties and especially to combat control of animal pests, in particular insects, arachnids and Nematodes used in agriculture, in forests, in the protection of stocks and materials as well as in the hygiene sector are suitable.

Die erfindungsgemäßen Fluorbutensäureamide sind durch die Formel (I) allgemein definiert.The fluorobutenamides according to the invention are general by the formula (I) Are defined.

Bevorzugte Substituenten bzw. Bereiche der in den oben und nachstehend erwähn­ ten Formeln aufgeführten Reste werden im folgenden erläutert:
R¹ steht bevorzugt für Wasserstoff, Fluor, Chlor oder Brom.
R² steht bevorzugt für Wasserstoff, C₁-C₆-Alkyl oder gegebenenfalls durch Fluor, Chlor, Brom oder C₁-C₄-Alkyl substituiertes Phenyl.
R³ steht bevorzugt für einen der unter a), b), c) oder d) genannten Reste.Preferred substituents or ranges of the radicals listed in the formulas mentioned above and below are explained below:
R1 is preferably hydrogen, fluorine, chlorine or bromine.
R² preferably represents hydrogen, C₁-C₆-alkyl or phenyl optionally substituted by fluorine, chlorine, bromine or C₁-C₄-alkyl.
R³ preferably represents one of the radicals mentioned under a), b), c) or d).

worin
X für Amino, Hydroxy, Mercapto, Nitro, Cyano, Fluor, Chlor, Brom, C₁-C₆-Alkyl, C₁-C₄-Halogenalkyl, C₁-C₆-Alkoxy, C₁-C₄-Halogenalkoxy, C₁-C₆-Alkylthio, C₁-C₄-Halogenalkylthio, C₁-C₆-Alkylsulfonyl, C₁-C₄-Halogen­ alkylsulfonyl, C₁-C₆-Alkylcarbonyl, C₁-C₆-Alkoxycarbonyl, C₁-C₆-Alkyl­ amino, Di-(C₁-C₆-alkyl)amino, Aminocarbonyl, C₁-C₆-Alkylaminocarbonyl, Di-(C₁-C₆-alkyl)aminocarbonyl oder C₂-C₆-Halogenalkenylcarbonylamino steht und
Y und Z unabhängig voneinander für Wasserstoff Amino, Hydroxy, Mercapto, Cyano, Carboxyl, Fluor, Chlor, Brom, C₁-C₆-Alkyl, C₁-C₄-Halogenalkyl, C₁-C₆-Alkoxy, C₁-C₄-Halogenalkoxy, C₁-C₆-Alkylthio, C₁-C₄-Halogenal­ kylthio, C₁-C₆-Alkylcarbonyl, C₁-C₆-Alkoxycarbonyl, C₁-C₆-Alkylamino, Di-(C₁-C₆-alkyl)amino, C₁-C₆-Alkylaminocarbonyl oder Di-(C₁-C₆-alkyl)­ aminocarbonyl stehen.wherein
X for amino, hydroxy, mercapto, nitro, cyano, fluorine, chlorine, bromine, C₁-C₆-alkyl, C₁-C₄-haloalkyl, C₁-C₆-alkoxy, C₁-C₄-haloalkoxy, C₁-C₆-alkylthio, C₁- C₄-Haloalkylthio, C₁-C₆-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl, C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylamino, di- (C₁-C₆-alkyl) amino, aminocarbonyl, C₁ -C₆-alkylaminocarbonyl, di- (C₁-C₆-alkyl) aminocarbonyl or C₂-C₆-haloalkenylcarbonylamino and
Y and Z independently of one another for hydrogen, amino, hydroxyl, mercapto, cyano, carboxyl, fluorine, chlorine, bromine, C₁-C₆-alkyl, C₁-C₄-haloalkyl, C₁-C₆-alkoxy, C₁-C₄-haloalkoxy, C₁-C₆ -Alkylthio, C₁-C₄-Halogenal kylthio, C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylamino, di- (C₁-C₆-alkyl) amino, C₁-C₆-alkylaminocarbonyl or di- (C₁- C₆-alkyl) aminocarbonyl.

worin
X und Y für die oben unter a) als jeweils bevorzugt für diese Substituenten genannten Bedeutungen stehen,
R⁴ für Wasserstoff oder C₁-C₄-Alkyl steht und
n für 0, 1 oder 2 steht.wherein
X and Y represent the meanings given above under a) as preferred for these substituents,
R⁴ represents hydrogen or C₁-C₄ alkyl and
n stands for 0, 1 or 2.

worin gegebenenfalls eine Methylengruppe durch SO₂ ersetzt ist oder eine oder zwei nicht direkt benachbarte Methylengruppen durch Sauerstoff Schwefel oder Stickstoff (welcher gegebenenfalls durch C₁-C₄-Alkyl, Phenyl oder Benzyl substituiert ist) ersetzt sind,
l für 0 oder 1 steht,
m für 0, 1, 2, 3, 4 oder 5 steht und
W für Fluor, Chlor, C₁-C₆-Alkyl oder gegebenenfalls durch Fluor, Chlor, Brom, C₁-C₄-Alkyl, C₁-C₄-Halogenalkyl, C₁-C₄-Alkoxy oder C₁-C₄-Halo­ genalkoxy substituiertes Phenyl steht.in which a methylene group is optionally replaced by SO₂ or one or two methylene groups which are not directly adjacent are replaced by oxygen, sulfur or nitrogen (which is optionally substituted by C₁-C₄-alkyl, phenyl or benzyl),
l represents 0 or 1,
m represents 0, 1, 2, 3, 4 or 5 and
W represents fluorine, chlorine, C₁-C₆-alkyl or phenyl which is optionally substituted by fluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C gen-halo.

d) Jeweils gegebenenfalls durch Fluor, Chlor, Brom, C₁-C₄-Alkyl oder durch gegebenenfalls durch Fluor, Chlor, C₁-C₄-Alkyl, C₁-C₄-Halogenalkyl, C₁-C₄-Alkoxy oder C₁-C₄-Halogenalkoxy substituiertes Phenyl substituiertes Pyridyl-C₁-C₂-alkyl, Furanyl-C₁-C₂-alkyl oder Thienyl-C₁-C₂-alkyl.d) in each case optionally by fluorine, chlorine, bromine, C₁-C₄-alkyl or phenyl optionally substituted by fluorine, chlorine, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy Pyridyl-C₁-C₂-alkyl, furanyl-C₁-C₂-alkyl or thienyl-C₁-C₂-alkyl.

R¹ steht besonders bevorzugt für Wasserstoff oder Fluor.
R² steht besonders bevorzugt für Wasserstoff oder C₁-C₄-Alkyl.
R³ steht besonders bevorzugt für einen der unter a), b), c) oder d) genannten Reste.R 1 particularly preferably represents hydrogen or fluorine.
R² particularly preferably represents hydrogen or C₁-C₄-alkyl.
R³ particularly preferably represents one of the radicals mentioned under a), b), c) or d).

worin
X für Mercapto, Nitro, Cyano, Fluor, Chlor, Brom, C₁-C₄-Alkoxy, C₁-C₄-Halogenalkoxy, C₁-C₄-Alkylthio, C₁-C₄-Alkylsulfonyl, C₁-C₂-Halogenal­ kylsulfonyl) C₁-C₄-Alkylcarbonyl, C₁-C₄-Alkylamino, Di-(C₁-C₄-alkyl)-amino, Aminocarbonyl oder C₃-C₅-Halogenalkenylcarbonylamino steht und
Y und Z unabhängig voneinander für Wasserstoff Fluor, Chlor, Carboxyl, C₁-C₄-Alkyl, C₁-C₄-Halogenalkyl, C₁-C₂-Alkylcarbonyl oder C₁ -C₄-Alkoxycarbonyl stehen.wherein
X for mercapto, nitro, cyano, fluorine, chlorine, bromine, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulfonyl, C₁-C₂-haloalksulfonyl) C₁-C₄-alkylcarbonyl , C₁-C₄-alkylamino, di- (C₁-C₄-alkyl) -amino, aminocarbonyl or C₃-C₅-haloalkenylcarbonylamino and
Y and Z independently of one another represent hydrogen, fluorine, chlorine, carboxyl, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₂-alkylcarbonyl or C₁-C₄-alkoxycarbonyl.

worin
X¹ für Fluor, Chlor oder C₁-C₄-Alkyl steht und
R⁴ für Wasserstoff Methyl oder Ethyl steht.wherein
X¹ is fluorine, chlorine or C₁-C₄ alkyl and
R⁴ represents hydrogen methyl or ethyl.

worin für m ≠ 0 gegebenenfalls eine Methylengruppe durch SO₂, Sauer­ stoff Schwefel oder Stickstoff (welcher gegebenenfalls durch C₁-C₄-Alkyl oder Benzyl substituiert ist) ersetzt ist,
l für 0 oder 1 steht und
m für 0, 2 oder 3 steht.wherein for m ≠ 0 a methylene group is optionally replaced by SO₂, oxygen, sulfur or nitrogen (which is optionally substituted by C₁-C₄ alkyl or benzyl),
l stands for 0 or 1 and
m stands for 0, 2 or 3.

d) Gegebenenfalls durch Fluor, Chlor, Methyl, Ethyl oder jeweils durch gegebenenfalls durch Fluor, Chlor oder Methyl substituiertes Phenyl substituiertes Furanylmethyl oder Pyridylmethyl.d) optionally by fluorine, chlorine, methyl, ethyl or in each case by phenyl optionally substituted by fluorine, chlorine or methyl substituted furanylmethyl or pyridylmethyl.

R¹ steht ganz besonders bevorzugt für Fluor.
R² steht ganz besonders bevorzugt für Wasserstoff oder Methyl.
R³ steht ganz besonders bevorzugt für einen der unter a), b), c) oder d) ge­ nannten Reste.R¹ very particularly preferably represents fluorine.
R² very particularly preferably represents hydrogen or methyl.
R³ very particularly preferably represents one of the radicals mentioned under a), b), c) or d).

worin
X für Nitro, Cyano, Fluor, Chlor, Brom, Methoxy, Trifluormethoxy, Methylthio, Methylsulfonyl, Ethylsulfonyl, Trifluormethylsulfonyl, Methyl­ carbonyl, Aminocarbonyl oder 3,4,4-Trifluorbut-3-en-1-yl-carbonylamino steht,
Y und Z unabhängig voneinander für Wasserstoff Fluor, Chlor, Carboxyl, Methyl, Ethyl, n-Propyl, iso-Propyl oder Trifluormethyl stehen.wherein
X represents nitro, cyano, fluorine, chlorine, bromine, methoxy, trifluoromethoxy, methylthio, methylsulfonyl, ethylsulfonyl, trifluoromethylsulfonyl, methylcarbonyl, aminocarbonyl or 3,4,4-trifluorobut-3-en-1-yl-carbonylamino,
Y and Z are independently hydrogen, fluorine, chlorine, carboxyl, methyl, ethyl, n-propyl, iso-propyl or trifluoromethyl.

worin
X¹ für Chlor steht und
R⁴ für Wasserstoff oder Methyl steht.wherein
X¹ represents chlorine and
R⁴ represents hydrogen or methyl.

Eine besonders hervorgehobene Gruppe von Verbindungen sind diejenigen Verbin­ dungen der Formel (I), in welchen R³ für einen der unter a) aufgeführten Reste steht.A particularly highlighted group of connections are those verbs dungen of formula (I), in which R³ for one of the radicals listed under a) stands.

Eine weitere besonders hervorgehobene Gruppe von Verbindungen sind diejenigen Verbindungen der Formel (I), in welchen R³ für einen der unter b) aufgeführten Reste steht.Another particularly highlighted group of compounds are those Compounds of formula (I) in which R³ for one of those listed under b) Leftovers.

Ebenfalls besonders hervorgehoben seien Verbindungen der Formel (I), in welchen R³ für einen der unter c) aufgeführten Reste steht.Compounds of the formula (I) in which R³ represents one of the radicals listed under c).

Die oben aufgeführten allgemeinen oder in Vorzugsbereichen aufgeführten Reste­ definitionen bzw. Erläuterungen gelten für die Endprodukte und für die Ausgangs- und Zwischenprodukte entsprechend. Diese Restedefinitionen können untereinander, also auch zwischen den jeweiligen Vorzugsbereichen, beliebig kombiniert werden.The radicals listed above or listed in preferred areas Definitions and explanations apply to the end products and to the initial and Intermediates accordingly. These residual definitions can be thus also be combined as desired between the respective preferred areas.

Erfindungsgemäß bevorzugt werden die Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als bevorzugt (vorzugsweise) aufgeführten Be­ deutungen vorliegt.According to the invention, preference is given to the compounds of the formula (I) in which a combination of the Be listed as preferred (preferred) interpretations are available.

Erfindungsgemäß besonders bevorzugt werden die Verbindungen der Formel (1), in welchen eine Kombination der vorstehend als besonders bevorzugt aufgeführten Bedeutungen vorliegt.According to the invention, particular preference is given to the compounds of the formula (1), in which are a combination of those listed as particularly preferred above Meanings exist.

Erfindungsgemäß ganz besonders bevorzugt werden die Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als ganz besonders bevorzugt aufgeführten Bedeutungen vorliegt.The compounds of the formula are very particularly preferred according to the invention (I) in which a combination of the above is particularly preferred listed meanings is present.

In den oben und nachstehend aufgeführten Restedefinitionen sind Kohlenwasser­ stoffreste, wie Alkyl oder Alkenyl, - auch in Verbindung mit Heteroatomen wie Alkoxy oder Alkylthio - soweit möglich, geradkettig oder verzweigt.In the residue definitions listed above and below are hydrocarbons material residues, such as alkyl or alkenyl, - also in combination with heteroatoms such as Alkoxy or alkylthio - as far as possible, straight-chain or branched.

Verwendet man bei der Herstellung von Verbindungen der Formel (I) z. B. 3,4,4-Trifluorbut-3-en-säurechlorid und 4-Bromanilin als Ausgangsstoffe, so kann der Reaktionsverlauf durch folgendes Reaktionsschema wiedergegeben werden:Is used in the preparation of compounds of formula (I) z. B. 3,4,4-trifluorobut-3-ene acid chloride and 4-bromoaniline as starting materials, so the The course of the reaction can be represented by the following reaction scheme:

Das oben beschriebene Verfahren zur Herstellung von Verbindungen der Formel (I) ist dadurch gekennzeichnet, daß man Amine der Formel (II) mit Säurechloriden der Formel (III) gegebenenfalls in Gegenwart eines Verdünnungsmittels und gege­ benenfalls in Gegenwart einer Base umsetzt.The method described above for the preparation of compounds of the formula (I) is characterized in that amines of the formula (II) with acid chlorides of formula (III) optionally in the presence of a diluent and against if necessary in the presence of a base.

Das erfindungsgemäße Verfahren wird vorzugsweise in Gegenwart eines Verdün­ nungsmittels durchgeführt.The process according to the invention is preferably carried out in the presence of a diluent carried out.

Als Verdünnungsmittel kommen insbesondere organische Lösungsmittel in Frage, beispielsweise gegebenenfalls chlorierte aliphatische oder aromatische Kohlenwas­ serstoffe wie Cyclohexan, Toluol, Xylol, Dichlormethan, Dichlorethan, Chloroform oder Chlorbenzol, Ether wie Diethylether, Dioxan oder Tetrahydrofuran oder Nitrile wie Acetonitril.Organic solvents are particularly suitable as diluents, for example optionally chlorinated aliphatic or aromatic coal water substances such as cyclohexane, toluene, xylene, dichloromethane, dichloroethane, chloroform or chlorobenzene, ethers such as diethyl ether, dioxane or tetrahydrofuran or Nitriles such as acetonitrile.

Als Verdünnungsmittel kommen auch Zweiphasensysteme, bestehend aus Wasser und einem organischen Lösungsmittel, in Frage, beispielsweise Wasser/Methylen­ chlorid oder Wasser/Toluol.Two-phase systems consisting of water also come as diluents and an organic solvent, for example water / methylene chloride or water / toluene.

Auch ein Überschuß des eingesetzten Amins der Formel (II) kommt als Ver­ dünnungsmittel in Frage.An excess of the amine of formula (II) used also comes as Ver fertilizer in question.

Als Base können prinzipiell alle für derartige Acylierungsreaktionen geeigneten or­ ganischen oder anorganischen Basen verwendet werden.In principle, all or suitable for such acylation reactions can be used as the base ganic or inorganic bases can be used.

Bevorzugt verwendet werden Amine, insbesondere tertiäre Amine wie Tri­ ethylamin, Diazabicycloundecen (DBU), Diazabicyclononen (DBN), Diazabicyclo­ octan (DABCO) oder Pyridin oder Alkali- oder Erdalkalicarbonate, -hydrogen­ carbonate oder -oxide. Beispielhaft seien Natriumcarbonat, Kaliumcarbonat, Na­ triumhydrogencarbonat und Calciumoxid genannt. Amines are preferably used, in particular tertiary amines such as tri ethylamine, diazabicycloundecene (DBU), diazabicyclonones (DBN), diazabicyclo octane (DABCO) or pyridine or alkali or alkaline earth carbonates, hydrogen carbonates or oxides. Examples include sodium carbonate, potassium carbonate, Na trium bicarbonate and calcium oxide called.  

Die Reaktionstemperatur kann in einem größeren Bereich variiert werden. Im allgemeinen arbeitet man bei Temperaturen zwischen -20°C und 140°C, bevorzugt zwischen 0°C und 60°C.The reaction temperature can be varied within a wide range. in the generally one works at temperatures between -20 ° C and 140 ° C, preferably between 0 ° C and 60 ° C.

Das Molverhältnis der Verbindung der Formel (II) zur Verbindung der Formel (III) beträgt im allgemeinen 2 : 1 bis 1 : 2.The molar ratio of the compound of formula (II) to the compound of formula (III) is generally 2: 1 to 1: 2.

Die Umsetzung wird im allgemeinen im Druckbereich von 0,5 bis 6 bar, vorzugs­ weise aber unter Normaldruck durchgeführt.The reaction is generally preferred in the pressure range from 0.5 to 6 bar wise but carried out under normal pressure.

Zur Aufarbeitung wird beispielsweise das Reaktionsgemisch hydroylsiert, das Pro­ dukt mit einem organischen Lösungsmittel wie Ethylacetat, Dichlormethan oder Toluol extrahiert und anschließend die organische Phase eingeengt.For working up, for example, the reaction mixture is hydroylated, the Pro product with an organic solvent such as ethyl acetate, dichloromethane or Extracted toluene and then concentrated the organic phase.

Die als Ausgangsstoffe benötigten Amine der Formel (II) sind bekannt und/oder lassen sich nach bekannten Methoden in einfacher Weise herstellen.The amines of the formula (II) required as starting materials are known and / or can be produced in a simple manner by known methods.

Die als Ausgangsstoffe benötigten Säurechloride der Formel (III) sind bekannt (s. z. B. US-5 389 680 sowie EP 432 861).The acid chlorides of the formula (III) required as starting materials are known (see. e.g. B. US-5 389 680 and EP 432 861).

Die Verbindungen der Formel (1) lassen sich auch herstellen, wenn man Amine der Formel (II) mit Carbonsäuren der Formel (IV)The compounds of formula (1) can also be prepared if amines of formula (II) with carboxylic acids of formula (IV)

in welcher
R¹ die obengenannte Bedeutung hat,
in Gegenwart eines reaktiven Hilfsstoffes wie Dicyclohexylcarbodiimid oder Carbonylbisimidazol in Gegenwart eines Verdünnungsmittels wie Tetrahydrofuran, Methylenchlorid oder Acetonitril umsetzt (vgl. Houben-Weyl, Methoden der Orga­ nischen Chemie, Band E5, S. 941 ff (1985)).in which
R¹ has the meaning given above,
in the presence of a reactive auxiliary such as dicyclohexylcarbodiimide or carbonylbisimidazole in the presence of a diluent such as tetrahydrofuran, methylene chloride or acetonitrile (cf. Houben-Weyl, Methods of Organic Chemistry, Volume E5, p. 941 ff (1985)).

Die Wirkstoffe eignen sich zur Bekämpfung von tierischen Schädlingen, insbeson­ dere Insekten, Spinnentieren und Nematoden, die in der Landwirtschaft, in Forsten, 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 Entwick­ lungsstadien wirksam. Zu den oben erwähnten Schädlingen gehören:
Aus der Ordnung der Isopoda z. B. Oniscus asellus, Armadillidium vulgare, Por­ cellioscaber.The active substances are suitable for controlling animal pests, in particular insects, arachnids and nematodes, which occur in agriculture, in forests, in the protection of stored goods and materials, and in the hygiene sector. They can preferably be used as pesticides. They are effective against normally sensitive and resistant species as well as against all or individual stages of development. The pests mentioned above include:
From the order of the Isopoda z. B. Oniscus asellus, Armadillidium vulgare, Por cellioscaber.

Aus der Ordnung der Diplopoda z. B. Blaniulus guttulatus.From the order of the Diplopoda z. B. Blaniulus guttulatus.

Aus der Ordnung der Chilopoda z. B. Geophilus carpophagus, Scutigera spec.From the order of the Chilopoda z. B. Geophilus carpophagus, Scutigera spec.

Aus der Ordnung der Symphyla z. B. Scutigerella immaculata.From the order of the Symphyla z. B. Scutigerella immaculata.

Aus der Ordnung der Thysanura z. B. Lepisma saccharina.From the order of the Thysanura z. B. Lepisma saccharina.

Aus der Ordnung der Collembola z. B. Onychiurus armatus.From the order of the Collembola z. B. Onychiurus armatus.

Aus der Ordnung der Orthoptera z. B. Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria.From the order of Orthoptera z. B. Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria.

Aus der Ordnung der Dermaptera z. B. Forficula auricularia.From the order of the Dermaptera z. B. Auricular Forficula.

Aus der Ordnung der Isoptera z. B. Reticulitermes spp.From the order of the Isoptera z. B. Reticulitermes spp.

Aus der Ordnung der Anoplura z. B. Pediculus humanus corporis, Haematopinus spp., Linognathus spp.From the order of the Anoplura z. B. Pediculus humanus corporis, Haematopinus spp., Linognathus spp.

Aus der Ordnung der Mallophaga z. B. Trichodectes spp., Damalinea spp.From the order of the Mallophaga z. B. Trichodectes spp., Damalinea spp.

Aus der Ordnung der Thysanoptera z. B. Hercinothrips femoralis, Thrips tabaci.From the order of the Thysanoptera z. B. Hercinothrips femoralis, Thrips tabaci.

Aus der Ordnung der Heteroptera z. B. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp. From the order of Heteroptera z. B. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.  

Aus der Ordnung der Homoptera z. B. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp., Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatüs, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.From the order of Homoptera z. B. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp., Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatüs, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.

Aus der Ordnung der Lepidoptera z. B. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Spodoptera exigua, Marnestra brassicae, Panolis flammea, Spodoptera litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana.From the order of the Lepidoptera z. B. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Spodoptera exigua, Marnestra brassicae, Panolis flammea, Spodoptera litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana.

Aus der Ordnung der Coleoptera z. B. Ahobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica.From the order of the Coleoptera z. B. Ahobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica.

Aus der Ordnung der Hymenoptera z. B. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.From the order of the Hymenoptera z. B. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.

Aus der Ordnung der Diptera z. B. Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa.From the order of the Diptera z. B. Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio  hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa.

Aus der Ordnung der Siphonaptera z. B. Xenopsylla cheopis, Ceratophyllus spp.From the order of the Siphonaptera z. B. Xenopsylla cheopis, Ceratophyllus spp.

Aus der Ordnung der Arachnida z. B. Scorpio maurus, Latrodectus mactans.From the order of the Arachnida z. B. Scorpio maurus, Latrodectus mactans.

Aus der Ordnung der Acarina z. B. Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp.From the order of Acarina z. B. Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp.

Zu den pflanzenparasitären Nematoden gehören z. B. Pratylenchus spp., Radopho­ lussimilis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp, Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp.The plant parasitic nematodes include z. B. Pratylenchus spp., Radopho lussimilis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp, Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp.

Die erfindungsgemäßen Verbindungen der Formel (I) zeichnen sich insbesondere durch eine hervorragende nematizide Wirkung, beispielsweise gegen Meloidogyne incognita und durch eine sehr gute akarizide Wirkung, beispielsweise gegen die gemeine Spinnmilbe (Tetranychus urticae) aus.The compounds of the formula (I) according to the invention are particularly noteworthy with an excellent nematicidal effect, for example against Meloidogyne incognita and by a very good acaricidal effect, for example against the common spider mite (Tetranychus urticae).

Sie besitzen auch eine blattinsektizide Wirkung und eine Wirkung gegen Pyri­ cularia oryzae am Reis.They also have leaf insecticidal activity and activity against pyri cularia oryzae on rice.

Die Wirkstoffe können in die üblichen Formulierungen überführt werden, wie Lö­ sungen, Emulsionen, Spritzpulver, Suspensionen, Pulver, Stäubemittel, Pasten, lös­ liche Pulver, Granulate, Suspensions-Emulsions-Konzentrate, Wirkstoff-impräg­ nierte Natur- und synthetische Stoffe sowie Feinstverkapselungen in polymeren Stoffen.The active ingredients can be converted into the usual formulations, such as Lö solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, sol Liche powder, granules, suspension emulsion concentrates, active ingredient impregnated nated natural and synthetic substances as well as very fine encapsulation in polymers Fabrics.

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 schaum­ erzeugenden Mitteln. These formulations are prepared in a known manner, e.g. B. by Mixing the active ingredients with extenders, i.e. liquid solvents and / or solid carriers, optionally using surface-active agents Agents, ie emulsifiers and / or dispersants and / or foam generating means.  

Im Falle der Benutzung von Wasser als Streckmittel können z. B. auch organische Lösungsmittel als Hilfslösungsmittel verwendet werden. Als flüssige Lösungsmittel kommen im wesentlichen in Frage: Aromaten, wie Xylol, Toluol, oder Alkylnaphthaline, clorierte Aromaten und chlorierte aliphatische Kohlenwasser­ stoffe, wie Chlorbenzole, Chlorethylene oder Methylenchlorid, aliphatische Koh­ lenwasserstoffe, 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 Cyclo­ hexanon, stark polare Lösungsmittel, wie Dimethylformamid und Dimethyl­ sulfoxid, sowie Wasser.In the case of the use of water as an extender, e.g. B. also organic Solvents are used as auxiliary solvents. As a liquid solvent essentially come into question: aromatics, such as xylene, toluene, or Alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons substances such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic Koh hydrogen, such as cyclohexane or paraffins, e.g. B. 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 cyclo hexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.

Als feste Trägerstoffe kommen in Frage:
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 Sägemehl, Kokosnußschalen, Maiskolben und Tabakstengeln; als Emulgier- und/oder schaumerzeugende Mittel kommen in Frage: z. B. nichtionogene und anionische Emulgatoren, wie Polyoxyethylen-Fett­ säure-Ester, Polyoxyethylen-Fettalkohol-Ether, z. B. Alkylaryl-polyglykolether, Al­ kylsulfonate, Alkylsulfate, Arylsulfonate sowie Einweißhydrolysate; als Dispergier­ mittel kommen in Frage: z. B. Lignin-Sulfitablaugen und Methylcellulose.The following are suitable as solid carriers:
e.g. B. ammonium salts and natural rock powders, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates, are suitable as solid carriers for granules: z. B. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foam-generating agents come into question: z. B. nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. B. alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; as a dispersing agent come into question: z. B. lignin sulfite and methyl cellulose.

Es können in den Formulierungen Haftmittel wie Carboxymethylcellulose, natür­ liche und synthetische pulvrige, körnige oder latexförmige Polymere verwendet werden, wie Gummiarabicum, Polyvinylalkohol, Polyvinylacetat, sowie natürliche Phospholipide, wie Kephaline und Lecithine und synthetische Phospholipide. Weitere Additive können mineralische und vegetabile Öle sein.Adhesives such as carboxymethyl cellulose, natural, can be used in the formulations Liche and synthetic powdery, granular or latex-shaped polymers used such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural Phospholipids such as cephalins and lecithins and synthetic phospholipids. Other additives can be mineral and vegetable oils.

Es können Farbstoffe wie anorganische Pigmente, z. B. Eisenoxid, Titanoxid, Ferrocyanblau und organische Farbstoffe, wie Alizarin-, Azo- und Metallphthalo­ cyaninfarbstoffe und Spurennährstoffe wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink verwendet werden. Dyes such as inorganic pigments, e.g. B. iron oxide, titanium oxide, Ferrocyan blue and organic dyes such as alizarin, azo and metal phthalalo cyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, Cobalt, molybdenum and zinc can be used.  

Die Formulierungen enthalten im allgemeinen zwischen 0,1 und 95 Gew.-% Wirkstoff vorzugsweise zwischen 0,5 und 90%.The formulations generally contain between 0.1 and 95% by weight 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 Stof­ fen oder Herbiziden vorliegen. Zu den Insektiziden zählen beispielsweise Phos­ phorsäureester, Carbamate, Carbonsäureester, chlorierte Kohlenwasserstoffe, Phe­ nylharnstoffe, durch Mikroorganismen hergestellte Stoffe u. a.
Besonders günstige Mischpartner sind z. B. die folgenden:The active compound according to the invention can be present in its commercially available formulations and in the use forms prepared from these formulations in a mixture with other active compounds, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides. The insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms and others
Particularly cheap mixing partners are e.g. B. the following:

Fungizide:
2-Aminobutan; 2-Ahilino-4-methyl-6-cydopropyl-pyrimidin; 2′,6′-Dibromo-2-me­ thyl-4′-trifluoromethoxy-4′-trifluoro-methyl-1,3-thiazol-5-carboxani-lid; 2,6-Di­ chloroN-(4-trifluoromethylbenzyl)-benzamid; (E)-2-Methoxyimino-N-methyl-2-(2- phenoxyphenyl)-acetamid; 8-Hydroxyquinolinsulfat; Methyl-(E)-2-{2-[6-(2-cyano­ phenoxy)-pyrimidin-4-yloxy]-phenyl}-3-methoxyacrylat; Methyl-(E)-methoxirmno [alpha-(o-tolyloxy)-o-tolyl]acetat; 2-Phenylphenol (OPP), Aldimorph, Ampropylfos, Anilazin, Azaconazol,
Benalaxyl, Benodanil, Benomyl, Binapacryl, Biphenyl, Bitertanol, Blasticidin-S, Bromuconazole, Bupirimate, Buthiobate,
Calciumpolysulfid, Captafol, Captan, Carbendazim, Carboxin, Chinomethionat (Quinomethionat), Chloroneb, Chloropicrin, Chlorothalonil, Chlozolinat, Cufraneb, Cymoxanil, Cyproconazole, Cyprofuram,
Dichlorophen, Diclobutrazol, Diclofluanid, Diclomezin, Dicloran, Diethofencarb, Difenoconazol, Dimethirimol, Dimethomorph, Diniconazol, Dinocap, Diphenyl­ amin, Dipyrithion, Ditalimfos, Dithianon, Dodine, Drazoxolon,
Edifenphos, Epoxyconazole, Ethirimol, Etridiazol,
Fenarimol, Fenbuconazole, Fenfuram, Fenitropan, Fenpiclonil, Fenpropidin, Fen­ propimorph, Fentinacetat, Fentinhydroxyd, Ferbam, Ferimzone, Fluazinam, Flu­ dioxonil, Fluoromide, Fluquinconazole, Flusilazole, Flusulfamide, Flutolanil, Flu­ triafol, Folpet, Fosetyl-Aluminium, Fthalide, Fuberidazd, Furalaxyl, Furmecyclox, Guazatine,
Hexachlorobenzol, Hexaconazol, Hymexazol,
Imazalil, Imibenconazol, Iminoctadin, Iprobenfos (IBP), Iprodion, Isoprothiolan,
Kasugamycin, Kupfer-Zubereitungen, wie: Kupferhydroxid, Kupfernaphthenat, Kupferoxychlorid, Kupfersulfat, Kupferoxid, Oxin-Kupfer und Bordeaux-Mi­ schung,
Mancopper, Mancozeb, Maneb, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfuroxam, Metiram, Metsulfovax, Myclobutanil,
Nickel-dimethyldithiocarbamat, Nitrothal-isopropyl, Nuarimol,
Ofurace, Oxadixyl, Oxamocarb, Oxycarboxin,
Pefurazoat, Penconazol, Pencycuron, Phosdiphen, Phthalid, Pimaricin, Piperalin, Polycarb amate, Polyoxin, Probenazol, Prochloraz, Procymidon, Propamocarb, Propiconazole, Propineb, Pyrazophos, Pyrifenox, Pyrimethanil, Pyroquilon,
Quintozen (PCNB),
Schwefel und Schwefel-Zubereitungen,
Tebuconazol, Tecloftalam, Tecnazen, Tetraconazol, Thiabendazol, Thicyofen, Thiophanat-methyl, Thiram, Tolclophos-methyl, Tolylfluanid, Triadimefon, Triadi­ menol, Triazoxid, Trichlamid, Tricyclazol, Tridemorph, Triflumizol, Triforin, Tri­ ticonazol,
Validamycin A, Vinclozolin,
Zineb, Ziram.Fungicides:
2-aminobutane; 2-ahilino-4-methyl-6-cydopropyl-pyrimidine; 2 ′, 6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoromethyl-1,3-thiazole-5-carboxanide; 2,6-di chloroN- (4-trifluoromethylbenzyl) benzamide; (E) -2-methoxyimino-N-methyl-2- (2-phenoxyphenyl) acetamide; 8-hydroxyquinoline sulfate; Methyl- (E) -2- {2- [6- (2-cyanophenoxy) pyrimidin-4-yloxy] phenyl} -3-methoxyacrylate; Methyl (E) methoxirmno [alpha- (o-tolyloxy) -o-tolyl] acetate; 2-phenylphenol (OPP), aldimorph, ampropylfos, anilazine, azaconazole,
Benalaxyl, Benodanil, Benomyl, Binapacryl, Biphenyl, Bitertanol, Blasticidin-S, Bromuconazole, Bupirimate, Buthiobate,
Calcium polysulfide, captafol, captan, carbendazim, carboxin, quinomethionate (quinomethionate), chloroneb, chloropicrin, chlorothalonil, chlozolinate, cufraneb, cymoxanil, cyproconazole, cyprofuram,
Dichlorophene, diclobutrazole, diclofluanid, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, dinocap, diphenylamine, dipyrithione, ditalimfos, dithianon, dodine, drazoxolone,
Edifenphos, epoxyconazole, ethirimol, etridiazole,
Fenarimol, Fenbuconazole, Fenfuram, Fenitropan, Fenpiclonil, Fenpropidin, Fen propimorph, Fentinacetat, Fentinhydroxyd, Ferbam, Ferimzone, Fluazinam, Flu dioxonil, Fluoromide, Fluquinconazole, Flusilazole, Flusulfamide, Flutolanil, Fulfinaflide, Flu triafolet , Furalaxyl, Furmecyclox, Guazatine,
Hexachlorobenzene, hexaconazole, hymexazole,
Imazalil, Imibenconazol, Iminoctadin, Iprobefos (IBP), Iprodione, Isoprothiolan,
Kasugamycin, copper preparations such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine copper and Bordeaux mixture,
Mancopper, Mancozeb, Maneb, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfuroxam, Metiram, Metsulfovax, Myclobutanil,
Nickel dimethyldithiocarbamate, nitrothal isopropyl, Nuarimol,
Ofurace, oxadixyl, oxamocarb, oxycarboxin,
Pefurazoate, penconazole, pencycuron, phosdiphen, phthalide, pimaricin, piperalin, polycarb amate, polyoxin, probenazole, prochloraz, procymidon, propamocarb, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilon,
Quintozen (PCNB),
Sulfur and sulfur preparations,
Tebuconazole, Tecloftalam, Tecnazen, Tetraconazole, Thiabendazole, Thicyofen, Thiophanat-methyl, Thiram, Tolclophos-methyl, Tolylfluanid, Triadimefon, Triadi menol, Triazoxid, Trichlamid, Tricyclazol, Tridemorph, Triforazol, Tri,
Validamycin A, vinclozolin,
Zineb, ziram.

Bakterizide:
Bronopol, Dichlorophen, Nitrapyrin, Nickel-Dimethyldithiocarbamat, Kasugamy­ cin, Octhilinon, Furancarbonsäure, Oxytetracyclin, Probenazol, Streptomycin, Tecloftalam, Kupfersulfat und andere Kupfer-Zubereitungen.Bactericides:
Bronopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, Kasugamy cin, octhilinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulfate and other copper preparations.

Insektizide/Akarizide/Nernatizide:
Abamectin, AC 303 630, Acephat, Acrinathrin, Alanycarb, Aldicarb, Alpha­ methrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azinphos A, Azinphos M, Azocyclotin,
Bacillus thuringiensis, Bendiocarb, Benfuracarb, Bensultap, Betacyfluthrin, Bifen­ thrin, BPMC, Brofenprox, Bromophos A, Bufencarb, Buprofezin, Butocarboxin, Butylpyridaben,
Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, CGA 1 57 419, CGA 184699, Chloethocarb, Chlorethoxyfos, Chlorfenvinphos, Chlor­ fluazuron, Chlormephos, Chlorpyrifos, Chlorpyrifos M, Cis-Resmethrin, Clocy­ thrin, Clofentezin, Cyanophos, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cyhexatin, Cypermethrin, Cyromazin,
Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Di­ azinon, Dichlofenthion, Dichlorvos, Dicliphos, Dicrotophos, Diethion, Diflu­ benzuron, Dimethoat, Dimethylvinphos, Dioxathion, Disulfoton,
Edifenphos, Emamectin, Esfenvalerat, Ethiofencarb, Ethion, Ethofenprox, Etho­ prophos, Etrimphos,
Fenamiphos, Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenprox, Fluva­ linate, Fonophos, Formothion, Fosthiazat, Fubfenprox, Furathiocarb,
HCH, Heptenophos, Hexaflumuron, Hexythiazox,
Imidacloprid, Iprobenfos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Iver­ mectin, Lambda-cyhalothrin, Lufenuron,
Malathion, Mecarbam, Mervinphos, Mesulfenphos, Metaldehyd, Methacrifos, Methamidophos, Methidathion, Methiocarb, Methomyl, Metolcarb, Milbemectin, Monocrotophos, Moxidectin,
Naled, NC 184, M 25, Nitenpyram,
Omethoat, Oxamyl, Oxydemethon M, Oxydeprofos,
Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenofos, Promecarb, Propaphos, Propoxur, Prothiofos, Prothoat, Pymetrozin, Pyrachlophos, Pyradaphenthion, Pyresmethrin, Pyrethrum, Pyridaben, Pyrimidifen, Pyriproxifen, Quinalphos,
RH 5992,
Salithion, Sebufos, Silafluofen, Sulfotep, Sulprofos,
Tebufenozid, Tebufenpyrad, Tebupirimphos, Teflubenzuron, Tefluthrin, Temephos, Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thio­ methon, Thionazin, Thuringiensin, Tralomethrin, Triarathen, Triazophos, Tri­ azuron, Trichlorfon, Triflumuron, Trimethacarb,
Vamidothion, XMC, Xylylcarb, XI 5301/5302, Zetamethrin.Insecticides / acaricides / nernicides:
Abamectin, AC 303 630, Acephat, Acrinathrin, Alanycarb, Aldicarb, Alpha methrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azinphos A, Azinphos M, Azocyclotin,
Bacillus thuringiensis, Bendiocarb, Benfuracarb, Bensultap, Betacyfluthrin, Bifen thrin, BPMC, Brofenprox, Bromophos A, Bufencarb, Buprofezin, Butocarboxin, Butylpyridaben,
Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, CGA 1 57 419, CGA 184699, Chloethocarb, Chlorethoxyfos, Chlorfenvinphos, Chlor fluazuron, Chlormephos, Chlorpyrifos, Chlorpyrifos M, Cis-Resmethrin, Clocyhrinhrhrhrhrhrhrhrinhrinhrinhrinhrinhrofhrinophrinophrine , Cyhalothrin, cyhexatin, cypermethrin, cyromazine,
Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Di azinon, Dichlofenthion, Dichlorvos, Dicliphos, Dicrotophos, Diethion, Diflu benzuron, Dimethoat, Dimethylvinphos, Dioxathion, Disulfoton,
Edifenphos, Emamectin, Esfenvalerat, Ethiofencarb, Ethion, Ethofenprox, Etho prophos, Etrimphos,
Fenamiphos, Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenothxatophion, Fufionophon, Fufionophon, Fufionophon, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufon, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufox
HCH, heptenophos, hexaflumuron, hexythiazox,
Imidacloprid, Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Iver mectin, Lambda-cyhalothrin, Lufenuron,
Malathion, Mecarbam, Mervinphos, Mesulfenphos, Metaldehyde, Methacrifos, Methamidophos, Methidathion, Methiocarb, Methomyl, Metolcarb, Milbemectin, Monocrotophos, Moxidectin,
Naled, NC 184, M 25, Nitenpyram,
Omethoate, Oxamyl, Oxydemethon M, Oxydeprofos,
Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenofos, Promecarb, Propaphos, Propoxur, Prothiofos, Prothoat, Pymetrozin, Pyrachlophhine, Pyrachlophhion, Pyrachlophion, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophion Pyridaben, Pyrimidifen, Pyriproxifen, Quinalphos,
RH 5992,
Salithion, Sebufos, Silafluofen, Sulfotep, Sulprofos,
Tebufenozid, Tebufenpyrad, Tebupirimphos, Teflubenzuron, Tefluthrin, Temephos, Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thio methon, Thionazin, Thuringiensin, Tralomichonon, Triaromenontron, Triaromenontron, Triarathenlarbon, Triarathenltronium, Triarathenltronium, Triarathenltronium, Triarathenltronium, Triarathenltronium, Triarathenltronium, Triaromenontrin, Triarathenltronium, Triaromenontrin, Triarathenltron, Triaromenontron
Vamidothione, XMC, xylylcarb, XI 5301/5302, zetamethrin.

Auch eine Mischung mit anderen bekannten Wirkstoffen, wie Herbiziden oder mit Düngemitteln und Wachstumsregulatoren ist möglich.A mixture with other known active ingredients, such as herbicides or with Fertilizers and growth regulators are possible.

Die erfindungsgemäßen Wirkstoffe können ferner in ihren handelsüblichen Formu­ lierungen 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 also be used in their commercially available form formulations and in the application forms prepared from these formulations in a mixture with synergists. Synergists are connections through which  the effect of the active ingredients is increased without the added synergist must be actively active itself.

Der Wirkstoffgehalt der aus den handelsüblichen Formulierungen bereiteten An­ wendungsformen kann in weiten Bereichen vanieren. Die Wirkstoffkonzentration der Anwendungsformen kann von 0,0000001 bis zu 95 Gew.-% Wirkstoff vorzugsweise zwischen 0,0001 und 1 Gew.-% liegen.The active ingredient content of the prepared from the commercially available formulations Forms of application can vary in many areas. The drug concentration The application forms can range from 0.0000001 to 95% by weight of active ingredient preferably between 0.0001 and 1% by weight.

Die Anwendung geschieht in einer den Anwendungsformen angepaßten üblichen Weise.The application takes place in a customary manner adapted to the application forms Wise.

Bei der Anwendung gegen Hygiene- und Vorratsschädlinge zeichnet sich der Wirkstoff durch eine hervorragende Residualwirkung auf Holz und Ton sowie durch eine gute Alkalistabilität auf gekälkten Unterlagen aus.When used against hygiene and storage pests, the stands out Active ingredient through an excellent residual effect on wood and clay as well due to good stability to alkali on limed substrates.

Die Herstellung und die Verwendung der erfindungsgemäßen Wirkstoffe gehen aus den nachfolgenden Beispielen hervor. The manufacture and use of the active compounds according to the invention start out the following examples.  

HerstellungsbeispielManufacturing example Beispiel 1example 1

Zur Lösung von 19,1 g (0,15 Mol) 4-Chloranilin in 200 ml Dichlormethan und 15,2 g (0,15 Mol) Triethylamin tropft man unter Eiskühlung und Rühren 23,8 g (0,15 Mol) 3,4,4-Trifluorbuten-3-säurechlorid, gelöst in 40 ml Dichlormethan. Nach 3 Stunden Rühren bei 20°C fügt man Wasser zu, trennt die organische Phase ab, wäscht diese mit verdünnter Salzsäure und anschließend mit Wasser. Nach dem Einengen der organischen Phase im Vakuum wird der Rückstand mit Petrol­ ether verrührt, abgesaugt und getrocknet. Man erhält 29,5 g N-(4-Chlorphenyl)- 3,4,4-trifluorbuten-3-carbonsäureamid vom Fp.: 124°C.For the solution of 19.1 g (0.15 mol) of 4-chloroaniline in 200 ml of dichloromethane and 15.2 g (0.15 mol) of triethylamine are added dropwise with ice cooling and stirring 23.8 g (0.15 mol) 3,4,4-trifluorobutene-3-acid chloride, dissolved in 40 ml dichloromethane. After stirring for 3 hours at 20 ° C., water is added and the organic phase is separated , wash it with dilute hydrochloric acid and then with water. After concentrating the organic phase in vacuo, the residue with petroleum ether stirred, suction filtered and dried. 29.5 g of N- (4-chlorophenyl) - are obtained. 3,4,4-trifluorobutene-3-carboxamide, mp: 124 ° C.

Analog bzw. gemäß den allgemeinen Angaben zur Herstellung erhält man die folgenden Verbindungen der Formel (I):Analogously or according to the general information on the preparation, the the following compounds of formula (I):

AnwendungsbeispielApplication example Beispiel AExample A

Grenzkonzentrations-Test/Nematoden
Testnematode: Meloidogyne incognita
Lösungsmittel: 4 Gewichtsteile Aceton
Emulgator: 1 Gewichtsteil Alkylarylpolyglykolether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Ge­ wichtsteil Wirkstoff mit der angegebenen Menge Lösungsmittel, gibt die angege­ bene Menge Emulgator zu und verdünnt das Konzentrat mit Wasser auf die ge­ wünschte Konzentration.Limit concentration test / nematodes
Test nematode: Meloidogyne incognita
Solvent: 4 parts by weight of acetone
Emulsifier: 1 part by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

Die Wirkstoffzubereitung wird innig mit Boden vermischt, der mit den Test­ nematoden stark verseucht ist. Dabei spielt die Konzentration des Wirkstoffs in der Zubereitung praktisch keine Rolle, entscheidend ist allein die Wirkstoffmenge pro Volumeneinheit Boden, welche in ppm (= mg/l) angegeben wird. Man füllt den behandelten Boden in Töpfe, sät Salat ein und hält die Töpfe bei einer Gewächs­ haus-Temperatur von 25°C.The active ingredient preparation is intimately mixed with soil, the one with the test nematodes is heavily contaminated. The concentration of the active ingredient plays in the Preparation practically does not matter, the decisive factor is the amount of active ingredient per Volume unit of soil, which is given in ppm (= mg / l). You fill it treated soil in pots, seeds lettuce and keeps the pots in a crop house temperature of 25 ° C.

Nach vier Wochen werden die Salatwurzeln auf Nematodenbefall (Wurzelgallen) untersucht und der Wirkungsgrad des Wirkstoffs in % bestimmt. Der Wirkungs­ grad ist 100%, wenn der Befall vollständig vermieden wird, er ist 0%, wenn der Befall genau so hoch ist wie bei den Kontrollpflanzen in unbehandeltem, aber in gleicher Weise verseuchtem Boden.After four weeks, the lettuce roots are attacked by nematodes (root galls) examined and the effectiveness of the active ingredient determined in%. The effect degree is 100% if the infestation is completely avoided, it is 0% if the Is just as high as in the control plants in untreated, but in same way contaminated soil.

Bei diesem Test besaßen z. B. die Verbindungen gemäß den Herstellungsbeispielen 1, 5, 15, 16, 17, 18, 19, 20, 21, 24, 25, 26, 27, 28 und 44 bei einer beispielhaften Wirkstoffkonzentration von 20 ppm einen Wirkungsgrad von 100%. In this test z. B. the compounds according to the preparation examples 1, 5, 15, 16, 17, 18, 19, 20, 21, 24, 25, 26, 27, 28 and 44 in an exemplary Active ingredient concentration of 20 ppm an efficiency of 100%.  

Beispiel BExample B

Tetranychus-Test (OP-resistent/Tauchbehandlung)
Lösungsmittel: 7 Gewichtsteile Dimethylformamid
Emulgator: 1 Gewichtsteil AlkylarylpolyglykoletherTetranychus test (OP-resistant / immersion treatment)
Solvent: 7 parts by weight of dimethylformamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether

Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Ge­ wichtsteil Wirkstoff mit der angegebenen Menge Lösungsmittel und der angege­ benen Menge Emulgator und verdünnt das Konzentrat mit Wasser auf die ge­ wünschte Konzentration.To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amount of solvent and the specified amount of emulsifier and dilute the concentrate with water to the wanted concentration.

Bohnenpflanzen (Phaseolus vulgaris), die stark von allen Entwicklungsstadien der gemeinen Spinnmilbe Tetranychus urticae befallen sind, werden in eine Wirkstoff­ zubereitung der gewünschten Konzentration getaucht.Bean plants (Phaseolus vulgaris), strongly affected by all stages of development Common spider mite Tetranychus urticae are infested in an active ingredient preparation of the desired concentration submerged.

Nach der gewünschten Zeit wird die Abtötung in % bestimmt. Dabei bedeutet 100%, daß alle Spinnmilben abgetötet wurden; 0% bedeutet, daß keine Spinn­ milben abgetötet wurden.After the desired time, the kill is determined in%. Here means 100% that all spider mites have been killed; 0% means that no spinning mites have been killed.

In diesem Test zeigten z. B. die Verbindungen gemäß den Herstellungsbeispielen 1, 13 und 19 bei einer beispielhaften Wirkstoffkonzentration von 0,01% eine Wir­ kung von mindestens 95% nach 13 Tagen.In this test, e.g. B. the compounds according to Preparation Examples 1, 13 and 19 at an exemplary active ingredient concentration of 0.01% reduction of at least 95% after 13 days.

Claims (7)

1. Verbindungen der Formel (I) in welcher
R¹ für Wasserstoff oder Halogen steht,
R² für Wasserstoff Alkyl oder gegebenenfalls durch Halogen oder Alkyl substituiertes Phenyl steht,
R³ für steht, worin
X für Amino, Hydroxy, Mercapto, Nitro, Cyano, Halo­ gen, Alkyl, Halogenalkyl, Alkoxy, Halogenalkoxy, Alkylthio, Halogenalkylthio, Alkylsulfonyl, Halogen­ alkylsulfonyl, Alkylcarbonyl, Alkoxycarbonyl, Al­ kylamino, Dialkylamino, Aminocarbonyl, Alkylaminocarbonyl, Dialkylaminocarbonyl oder Halogenal­ kenylcarbonylamino steht,
Y und Z unabhängig voneinander für Wasserstoff Amino, Hydroxy, Mercapto, Cyano, Carboxyl, Halogen, Al­ kyl, Halogenalkyl, Alkoxy, Halogenalkoxy, Alkylthio, Halogenalkylthio, Alkylcarbonyl, Alkoxycarbonyl, Alkylamino, Dialkylamino, Alkylaminocarbonyl oder Dialkylaminocarbonyl stehen oder steht, worin
X und Y die oben angegebene Bedeutung haben,
R⁴ für Wasserstoff oder Alkyl steht und
n für 0, 1, 2, 3 oder 4 steht oder worin
gegebenenfalls eine Methylengruppe durch SO₂ ersetzt ist oder eine oder zwei nicht direkt benachbarte Methylengrup­ pen im Ring durch Sauerstoff Schwefel oder Stickstoff (welcher gegebenenfalls durch Alkyl, Phenyl oder Benzyl substituiert ist) ersetzt sind,
l für 0, 1 oder 2 steht,
m für 0, 1, 2, 3, 4 oder 5 steht und
W für Halogen, Alkyl oder gegebenenfalls durch Halo­ gen, Alkyl, Halogenalkyl, Alkoxy oder Halogenalk­ oxy substituiertes Phenyl steht oder
  • d) gegebenenfalls durch Halogen, Alkyl oder durch gegebenen­ falls durch Halogen, Alkyl, Halogenalkyl, Alkoxy oder Halo­ genalkoxy substituiertes Phenyl substituiertes 5- oder 6-glie­ driges Hetarylalkyl steht mit ein bis drei Heteroatomen aus der Reihe Sauerstoff Schwefel und Stickstoff.
1. Compounds of formula (I) in which
R¹ represents hydrogen or halogen,
R² represents hydrogen alkyl or phenyl optionally substituted by halogen or alkyl,
R³ for stands in what
X represents amino, hydroxy, mercapto, nitro, cyano, halo, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfonyl, haloalkylsulfonyl, alkylcarbonyl, alkoxycarbonyl, alkylamino, dialkylamino, aminocarbonyl, alkylaminocarbonyl, dialkylalinoaminocarbonyl or haloalkylamino carbonyl ,
Y and Z independently of one another represent hydrogen, amino, hydroxy, mercapto, cyano, carboxyl, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylcarbonyl, alkoxycarbonyl, alkylamino, dialkylamino, alkylaminocarbonyl or dialkylaminocarbonyl or stands in what
X and Y have the meaning given above,
R⁴ represents hydrogen or alkyl and
n stands for 0, 1, 2, 3 or 4 or wherein
optionally a methylene group is replaced by SO₂ or one or two not directly adjacent methylene groups in the ring are replaced by oxygen, sulfur or nitrogen (which is optionally substituted by alkyl, phenyl or benzyl),
l represents 0, 1 or 2,
m represents 0, 1, 2, 3, 4 or 5 and
W represents halogen, alkyl or phenyl optionally substituted by halo, alkyl, haloalkyl, alkoxy or haloalkoxy or
  • d) optionally substituted by halogen, alkyl or by optionally substituted by halogen, alkyl, haloalkyl, alkoxy or halo genalkoxy substituted 5- or 6-glazed hetarylalkyl is one to three heteroatoms from the series oxygen, sulfur and nitrogen.
2. Verfahren zur Herstellung von Verbindungen der Formel (I) gemäß Anspruch 1, dadurch gekennzeichnet, daß man
Amine der Formel (II) HNR²R³ (II)in welcher
R² und R³ die oben angegebene Bedeutung haben,
mit Säurechloriden der Formel (III) in welcher
R¹ die oben angegebene Bedeutung hat,
gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart einer Base umsetzt.2. A process for the preparation of compounds of formula (I) according to claim 1, characterized in that
Amines of the formula (II) HNR²R³ (II) in which
R² and R³ have the meaning given above,
with acid chlorides of the formula (III) in which
R¹ has the meaning given above,
if appropriate in the presence of a diluent and if appropriate in the presence of a base. 3. Schädlingsbekämpfungsmittel, gekennzeichnet durch einen Gehalt an min­ destens einer Verbindung der Formel (I) gemäß Anspruch 1.3. pesticide, characterized by a content of min at least one compound of formula (I) according to claim 1. 4. Verwendung von Verbindungen der Formel (I) gemäß Anspruch 1 zur Be­ kämpfung von Schädlingen. 4. Use of compounds of formula (I) according to claim 1 for loading pest control.   5. Verfahren zur Bekämpfung von Schädlingen, dadurch gekennzeichnet, daß man Verbindungen der Formel (1) gemäß Anspruch 1 auf Schädlinge und/oder ihren Lebensraum einwirken läßt.5. A method for controlling pests, characterized in that compounds of formula (1) according to claim 1 on pests and / or let their living space take effect. 6. Verfahren zur Herstellung von Schädlingsbekämpfungsmitteln, dadurch gekennzeichnet, daß man Verbindungen der Formel (I) gemäß Anspruch 1 mit Streckmitteln und/oder oberflächenaktiven Mitteln vermischt.6. Process for the preparation of pesticides, thereby characterized in that compounds of the formula (I) according to Claim 1 mixed with extenders and / or surfactants. 7. Verwendung von Verbindungen der Formel (I) gemäß Anspruch 1 zur Herstellung von Schädlingsbekämpfungsmitteln.7. Use of compounds of formula (I) according to claim 1 for Manufacture of pesticides.
DE19531300A 1995-08-25 1995-08-25 Fluorobutenic acid amides Withdrawn DE19531300A1 (en)

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DE19531300A DE19531300A1 (en) 1995-08-25 1995-08-25 Fluorobutenic acid amides
EP96929247A EP0848698A1 (en) 1995-08-25 1996-08-13 Fluorobutene acid amides
CA002230100A CA2230100A1 (en) 1995-08-25 1996-08-13 Fluorobutene acid amides
JP9509775A JPH11511438A (en) 1995-08-25 1996-08-13 Fluorobutenoic acid amide
PCT/EP1996/003570 WO1997008132A1 (en) 1995-08-25 1996-08-13 Fluorobutene acid amides
CN96197624A CN1200109A (en) 1995-08-25 1996-08-13 Fluorobutene acid amides
KR1019980701266A KR19990044034A (en) 1995-08-25 1996-08-13 Fluorobutene Acid Amide
AU68729/96A AU6872996A (en) 1995-08-25 1996-08-13 Fluorobutene acid amides
BR9610023A BR9610023A (en) 1995-08-25 1996-08-13 Fluorine butenamides
TR1998/00297T TR199800297T1 (en) 1995-08-25 1996-08-13 Fluorobutenamides on.
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BR (1) BR9610023A (en)
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US6852888B2 (en) * 1998-06-02 2005-02-08 Syngenta Crop Protection, Inc. Carboxylic acid derivatives
WO2007089455A1 (en) * 2006-01-27 2007-08-09 E. I. Du Pont De Nemours And Company Fluoroalkenyl derivatives as insecticides and nematicides
WO2013144179A1 (en) * 2012-03-28 2013-10-03 Intervet International B.V. Heteroaryl compounds with a-cyclic bridging unit
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US6852888B2 (en) * 1998-06-02 2005-02-08 Syngenta Crop Protection, Inc. Carboxylic acid derivatives
WO2007089455A1 (en) * 2006-01-27 2007-08-09 E. I. Du Pont De Nemours And Company Fluoroalkenyl derivatives as insecticides and nematicides
WO2013144179A1 (en) * 2012-03-28 2013-10-03 Intervet International B.V. Heteroaryl compounds with a-cyclic bridging unit
US9321724B2 (en) 2012-03-28 2016-04-26 Intervet Inc. Heteroaryl compounds with A-cyclic bridging unit
WO2020144695A1 (en) * 2019-01-09 2020-07-16 Yeda Research And Development Co. Ltd. Modulators of pin1 activity and uses thereof

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BR9610023A (en) 1999-07-06
JPH11511438A (en) 1999-10-05
MX9801493A (en) 1998-08-30
TR199800297T1 (en) 1998-05-21
CN1200109A (en) 1998-11-25
CA2230100A1 (en) 1997-03-06
KR19990044034A (en) 1999-06-25
AU6872996A (en) 1997-03-19
WO1997008132A1 (en) 1997-03-06

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