WO2006058730A1 - Composes d'hydrazide pour lutter contre des parasites animaux - Google Patents

Composes d'hydrazide pour lutter contre des parasites animaux Download PDF

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Publication number
WO2006058730A1
WO2006058730A1 PCT/EP2005/012787 EP2005012787W WO2006058730A1 WO 2006058730 A1 WO2006058730 A1 WO 2006058730A1 EP 2005012787 W EP2005012787 W EP 2005012787W WO 2006058730 A1 WO2006058730 A1 WO 2006058730A1
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Prior art keywords
crc
alkyl
phenyl
formula
haloalkyl
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PCT/EP2005/012787
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English (en)
Inventor
Michael Hofmann
Michael Rack
David G. Kuhn
Deborah L. Culbertson
Douglas Anspaugh
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Basf Aktiengesellschaft
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Priority to AU2005311429A priority Critical patent/AU2005311429A1/en
Priority to US11/791,919 priority patent/US20070265231A1/en
Priority to MX2007006538A priority patent/MX2007006538A/es
Priority to JP2007543768A priority patent/JP2008521856A/ja
Priority to AP2007004018A priority patent/AP2007004018A0/xx
Priority to BRPI0518725-7A priority patent/BRPI0518725A2/pt
Priority to EP05810640A priority patent/EP1819224A1/fr
Publication of WO2006058730A1 publication Critical patent/WO2006058730A1/fr
Priority to IL183198A priority patent/IL183198A0/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
    • C07C243/38—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C243/42—Hydrazines having nitrogen atoms of hydrazine groups further singly-bound to hetero atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • A01N37/28—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 containing the group; 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
    • 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/12—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings condensed with a carbocyclic ring
    • A—HUMAN NECESSITIES
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/20—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—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
    • C07D307/56—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 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
    • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—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
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to new hydrazide compounds which are useful for combating animal pests, in particular insects, arachnids and nematodes.
  • the invention also relates to a method for combating insects, nematodes and arachnids.
  • JP 2000169461 describes inter alia thiadiazolylcarbonylhydrazones of phenylketones having insecticidal or fungicidal activity. However, the insecticidal activity of these compounds is not satisfactory.
  • Ar is an optionally substituted cyclic radical, selected from phenyl, napthyl and heterocyclic radicals, n is 0 or 1 , Y is inter alia CO or SO 2 , R 1a is H, d-Cio-alkyl, C 1 - C-io-haloalkyl, C 3 -C 10 -cycloalkyl, C 3 -C 10 -halocycloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 - haloalkenyl, C 2 -C 10 -alkynyl, C 2 -C 10 -haloalkynyl or optionally substituted phenyl, R 2a and R 3a are inter alia H, Ci-C 10 -alkyl, CrCio-haloalkyl, halogen, optionally substituted phenyl or cyano and R 4a is inter alia an optionally substituted aromatic radical selected from phenyl,
  • A is a cyclic radical selected from phenyl and a 5- or 6-membered heterocyclic radical with 1 to 4 heteroatoms as ring members which are selected, independently of one another, from O, N and S, the 5- or 6-membered heterocyclic radical may have a carbonyl group as ring member, and where the cyclic radical may have 1 , 2, 3, 4 or 5 substituents R a which are selected, independently of one another, from halogen, cyano, nitro, CrC 10 -alkyl, CrC 1o -haloalkyl, C 3 -C 10 -cycloalkyl, C 3 - C 10 -halocycloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -haloalkenyl, C 2 -C 10 -alkynyl, C 3 -C 10 - haloalkynyl, CrC ⁇ -alkoxy, CrC 10 -haloalkoxy, C 2
  • R b which are selected, independently of one another, from halogen, cyano, nitro, C r Cio-alkyl, Ci-C 10 -haloalkyl, C 3 -C 10 -cycloalkyl, C 3 - C 10 -halocycloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -haloalkenyl, C 2 -C 10 -alkynyl, C 3 -Ci 0 - haloalkynyl, CrCi 0 -alkoxy, CrC 10 -haloalkoxy, C 2 -C 10 -alkenyloxy, C 2 -Ci 0 - haloalkenyloxy, C 2 -C 10 -alkynyloxy, C 3 -C 10 -haloalkynyloxy, Ci-C 10 -alkylthio, C 1 -
  • Q is selected from the group consisting of a single bond, C r C 4 alkylidene,
  • Ar is an aromatic radical selected from phenyl, naphthyl, pyridyl, pyrimidyl, furyl and thienyl, where the aromatic radical may carry 1 , 2, 3, 4 or 5 substituents R c which are selected, independently of one another, from halogen, cyano, nitro, C 1 -C 10 - alkyl, C r Ci 0 -haloalkyl, C 3 -Ci 0 -cycloalkyl, C 3 -C 10 -halocycloalkyl, C 2 -Ci 0 -alkenyl,
  • R 1 is selected from the group consisiting of H, Ci-C 10 -alkyl, Ci-Ci 0 -haloalkyl, C 3 -C 10 - cycloalkyl, C 3 -C 1o -halocycloalkyl, C 2 -C 1o -alkenyl, C 2 -C 10 -haloalkenyl, C 2 -C 10 - alkynyl, C 2 -C 10 -haloalkynyl, phenyl and a 5- or 6-membered heterocyclic radical with 1 to 4 heteroatoms which are selected, independently of one another, from O, N and S, it being possible for the aforementioned two last radicals to be unsubstituted or substituted by 1 , 2, 3, 4 or 5 substituents R a as defined above;
  • R 2 is a monovalent radical selected from H, halogen, cyano, Ci-C 1o -alkyl, C 1 -C 10 - haloalkyl, C 3 -C 1o -cycloalkyl, C 3 -C 10 -halocycloalkyl, C 2 -Ci 0 -alkenyl, C 2 -C 10 - haloalkenyl, C 2 -C 1o -alkynyl, C 3 -C 10 -haloalkynyl, d-C 10 -alkoxy, C r C 10 -haloalkoxy, C 2 -C 10 -alkenyloxy, C 2 -C 10 -haloalkenyloxy, C 2 -C 10 -alkynyloxy, C 3 -C 10 - haloalkynyloxy, d-C 10 -alkylthio, CrC 10 -haloalkylthio, hydroxy
  • R 3 is selected from the group consisiting of H, halogen, cyano, CrC 1o -alkyl, C 1 -C 10 - haloalkyl, C 3 -C 1o -cycloalkyl, Qrdo-halocycloalkyl, C 2 -C 1o -alkenyl, C 2 -C 10 - haloalkenyl, C 2 -C 1o -alkynyl, C 3 -C 10 -haloalkynyl, C 1 -C 1 CaIkOXy, d-do-haloalkoxy, C 2 -C 10 -alkenyloxy, C 2 -C 1o -haloalkenyloxy, C 2 -Ci 0 -alkynyloxy, C 3 -C 10 - haloalkynyloxy, d-C ⁇ -alkylthio, CrC 1o -haloalkylthio,
  • R 4 is hydrogen or has one of the meanings given for R c or
  • N N, 0-CR 11 R 12 , S-CR 11 R 12 , N(R 13 )-CR 11 R 12 , O-C(O), O-C(S), S-C(O); N(R 13 )-C(O) or N(R 13 )-C(S);
  • R 5 is selected from the group consisiting of H, d-do-alkyl. d-do-haloalkyl, C 3 -C 10 - cycloalkyl, C 3 -C 10 -halocycloalkyl, C 2 -C 10 -alkenyl, C 2 -C 1o -haloalkenyl, C 2 -C 10 - alkynyl, C 2 -Ci 0 -haloalkynyl, benzyl and phenyl wherein benzyl and phenyl may be substituted by 1 , 2, 3, 4 or 5 substituents R d which are selected, independently of one another, from halogen, cyano, nitro, Ci-Ci O -alkyl, C ⁇ do-haloalkyl, C 3 -C 10 - cycloalkyl, C 3 -C 10 -halocycloalkyI, C 2 -Ci 0 -alkeny
  • R 6 is selected from the group consisiting of H, Ci-C 10 -alkyl optionally substituted by CN or NO 2 , C r C 1o -haloalkyl, C 3 -C 10 -cycloalkyl, C 3 -C 10 -halocycloalkyl, C 2 -C 10 - alkenyl, C 2 -Ci 0 -haloalkenyl, C 2 -C 10 -alkynyl, C 2 -C 10 -haloalkynyl, CrC-io-alkylthio,
  • R 7 , R 8 are selected independently of one another from H, CrC 1o -alkyl, CrCio-haloalkyl, C 3 -C 1o -cycloalkyl, C 3 -C 10 -halocycloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -haloalkenyl, C 2 - C 1o -alkynyl, C 3 -C 10 -haloalkynyl, phenyl, benzoyl, naphthyl or benzyl wherein the phenyl ring in the aforementioned four radicals may be substituted by 1 , 2, 3, 4 or 5 substituents which are selected, independently of one another, from halogen, cyano, nitro, Ci-Ci O -alkyl, C r C 1o -haloalkyl, C 3 -C 10 -cycloalkyl, C 3 -C 10 - halocycloalky
  • R 9 is hydrogen, cyano, d-Ci O -alkyl, d-Cio-haloalkyl, C 3 -C 10 -cycloalkyl, C 3 -Ci 0 - halocycloalkyl, C 2 -Ci 0 -alkenyl, C 2 -Ci 0 -haloalkenyl, C 2 -Ci 0 -alkynyl, C 3 -Ci 0 - haloalkynyl, Ci-Ci ⁇ -haloalkylsulfonyl, Ci-C 10 -alkylcarbonyl, C 1 -C 10 - haloalkylcarbonyl, R 7 R 8 N-CO-, phenyl or benzyl, wherein phenyl and benzyl may be substituted by 1 , 2, 3, 4 or 5 substituents R b ; and
  • R 10 is hydrogen or has one of the meanings given for R c ;
  • R 11 , R 12 are selected independently of one another from H, d-C 10 -alkyl, C 1 -C 10 - haloalkyl, C 3 -Ci 0 -cycloalkyl, C 3 -C 10 -halocycloalkyl, C 2 -C 10 -alkenyl, C 2 -Ci 0 - haloalkenyl, C 2 -Ci o -alkynyl and C 3 -Ci 0 -haloalkynyl, C r Ci 0 -alkoxy, C 1 -C 10 - haloalkoxy, d-do-alkylthio, C r C 1o -haloalkylthio, hydroxy-C r Ci 0 -alkyl, C 1 -C 10 - alkoxy-Ci-Ci 0 -alkyl, halo-Ci-Ci 0 -alkoxy-Ci-C
  • R 13 is hydrogen, cyano, Ci-Ci ⁇ -alkyl, Ci-Ci 0 -haloalkyl, C 3 -Ci 0 -cycloalkyl, C 3 -C 10 - halocycloalkyl, C 2 -C 10 -alkenyl, C 2 -Ci ⁇ -haloalkenyl, C 2 -Ci 0 -alkynyl, C 3 -Ci 0 - haloalkynyl, CrC 10 -haloalkylsulfonyl, CrCio-alkylcarbonyl, CrC 10 - haloalkylcarbonyl, R 7 R 8 N-CO-, phenyl or benzyl, wherein phenyl and benzyl may be substituted by 1 , 2, 3, 4 or 5 substituents R b ;
  • the compounds of the general formula I can be used for controlling pests, selected from harmful insects, arachnids and nematodes.
  • the compounds of the formula I are in particular useful from combating insects.
  • compositions for combating such pests preferably in the form of directly sprayable solutions, emulsions, pastes, oil dispersions, powders, materials for scattering, dusts or in the form of granules, which comprises a pesticidally effective amount of at least one compound of the general formula I or at least a salt thereof and at least one carrier which may be liquid and/or solid and which is prefarably agronomically acceptable, and/or at least one surfactant.
  • the invention provides a method for combating such pests, which comprises contacting said pests, their habitat, breeding ground, food supply, plant, seed, soil, area, material or environment in which the animal pests are growing or may grow, or the materials, plants, seeds, soils, surfaces or spaces to be protected from an attack of or infestation by said pest, with a pesticidally effective amount of a compound of the general formula I as defined herein or a salt thereof.
  • the invention provides in particular a method for protecting crops, including seeds, from attack or infestation by harmful insects, arachnids and/or nematodes, said method comprises contacting a crop with a pesticidally effective amount of at least one compound of formula I as defined herein or with a salt thereof.
  • the invention also provides a method for protecting non-living materials from attack or infestation by the aforementioned pests, which method comprises contacting the nonliving material with a pesticidally effective amount of at least one compound of formula I as defined herein or with a salt thereof.
  • the present invention provides both the pure enantiomes or diastereomers or mixtures thereof, the pure cis- and trans-isomers and the mixtures thereof.
  • the compounds of the general formula I may also exist in the form of different tautomers if A or Ar carry amino or hydroxy groups. The invention comprises the single tautomers, if seperable, as well as the tautomer mixtures.
  • Salts of the compounds of the formula I are preferably agriculturally acceptable salts. They can be formed in a customary method, e.g. by reacting the compound with an acid of the anion in question if the compound of formula I has a basic functionality or by reacting an acidic compound of formula I with a suitable base.
  • Suitable agriculturally useful salts are especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, do not have any adverse effect on the action of the compounds according to the present invention.
  • Suitable cations are in particular the ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium (NH 4 + ) and substituted ammonium in which one to four of the hydrogen atoms are replaced by CrC 4 -alkyl, CrC 4 -hydroxyalkyl, C 1 -C 4 ⁇ IkOXy, C 1 -C 4 -BIkOXy-C 1 - C 4 -alkyl, hydroxy-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, phenyl or benzyl.
  • substituted ammonium ions comprise methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2- hydroxyethoxy)ethylammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzyltriethylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(C r C 4 -alkyl)sulfonium, and sulfoxonium ions, preferably tri(C 1 -C 4 -alkyl)sulfoxonium.
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of CrC ⁇ alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting the compounds of the formula I with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
  • the organic moieties mentioned in the above definitions of the variables are - like the term halogen - collective terms for individual listings of the individual group members.
  • the prefix C n -C m indicates in each case the possible number of carbon atoms in the group.
  • Halogen or "halo” will be taken to mean fluoro, chloro, bromo and iodo.
  • the substituent O denotes a carbonyl group.
  • O-CrC 4 -alkylidene and "S-C r C 4 -alkylidene”, respectively refer to a linear or branched alkanediyl group having 1 to 4 carbon atoms, where one valency is attached to the skeleton via an oxygen or sulfur atom, respectively.
  • d-C ⁇ -alkyl refers to a branched or unbranched saturated hydrocarbon group having 1 to 10 carbon atoms, for example methyl, ethyl, propyl, 1-methylethyl, butyl, 1- methylpropyl, 2-methylpropyl, 1 ,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3- methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2- dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 ,1- dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3-di
  • C r C 4 -alkyl means for example methyl, ethyl, propyl, 1- methylethyl, butyl, 1 -methylpropyl, 2-methylpropyl or 1 ,1-dimethylethyl.
  • Cio-haloalkyl refers to a straight-chain or branched alkyl group having 1 to 10 carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, for example Ci-C 4 - haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2- difluoroethyl, 2,2,2-trifluoroethyl, 2-chlor
  • C 1 - C 10 -haloalkyl in particular comprises CrCa-fluoroalkyl, which is synonym with methyl or ethyl, wherein 1 , 2, 3, 4 or 5 hydrogen atoms are substituted by fluorine atoms, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2- difluoroethyl, 2,2,2-trifluoroethyl and pentafluoromethyl.
  • d-Cio-alkoxy and “C-i-C-io-alkylthio” refer to straight-chain or branched alkyl groups having 1 to 10 carbon atoms (as mentioned above) bonded through oxygen or sulfur linkages, respectively, in any position in the alkyl group.
  • Examples include C 1 -C 4 - alkoxy such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, isobutoxy and tert-butoxy, further CrC 4 -alkylthio such as methylthio, ethylthio, propylthio, isopropylthio, and n-butylthio.
  • Ci-C 10 -haloalkoxy and " refer to straight- chain or branched alkyl groups having 1 to 10 carbon atoms (as mentioned above) bonded through oxygen or sulfur linkages, respectively, in any position in the alkyl group, where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, for example C 1 -C 2 -IIaIOaIkOXy, such as chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroe
  • C r C 2 -fluoroalkoxy and C 1 -C 2 - fluoroalkylthio refer to Ci-C 2 -fluoroalkyl which is bound to the remainder of the molecule via an oxygen atom or a sulfur atom, respectively.
  • C 2 -C 10 -alkenyl intends a branched or unbranched unsaturated hydrocarbon group having 2 to 10 carbon atoms and a double bond in any position, such as ethenyl, 1-propenyl, 2-propenyl, 1-methyl-ethenyl, 1-butenyl, 2- butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2- methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyM-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3- methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1 ,1- dimethyl-2
  • C 2 -C 10 -haloalkenyl intends a branched or unbranched unsaturated hydrocarbon group having 2 to 10 carbon atoms and a double bond in any position, where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above.
  • C 2 -C 10 -alkenyloxy intends a branched or unbranched unsaturated hydrocarbon group having 2 to 10 carbon atoms and a double bond in any position, the alkenyl group being bonded through oxygen linkage, in any position in the alkenyl group, for example ethenyloxy, propenyloxy and the like.
  • C 2 -C 10 -haloalkenyloxy intends a branched or unbranched unsaturated hydrocarbon group having 2 to 10 carbon atoms and a double bond in any position, the alkenyl group being bonded through oxygen linkage, , in any position in the alkenyl group, where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above.
  • C 2 -C 10 -alkynyl refers to a branched or unbranched unsaturated hydrocarbon group having 2 to 10 carbon atoms and containing at least one triple bond, such as ethynyl, propynyl, 1-butynyl, 2-butynyl, and the like.
  • C 3 -C 10 -haloalkynyr refers to a branched or unbranched unsaturated hydrocarbon group having 3 to 10 carbon atoms and containing at least one triple bond, where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, with the proviso that the halogen atom is not directly bound to the triple bond.
  • C 2 -C 10 -alkynyloxy refers to a branched or unbranched unsaturated hydrocarbon group having 2 to 10 carbon atoms and containing at least one triple bond, the alkynyl group being bonded through oxygen linkage in any position in the alkynyl group.
  • C 3 -C 10 -haloalkynyloxy refers to a branched or unbranched unsaturated hydrocarbon group having 3 to 10 carbon atoms and containing at least one triple bond, the group being bonded through oxygen linkages in any position in the alkynyl group, where some or all of the hydrogen atoms in these group may be replaced by halogen atoms as mentioned above, with the proviso that the halogen atom is not directly bound to the triple bond.
  • C 3 -C 10 -cycloalkyl refers to a monocyclic 3- to 10-membered saturated carbon atom ring, e.g. cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and cyclodecyl.
  • C 3 -C 10 -halocycloalkyr refers to a monocyclic 3- to 10- membered saturated carbon atom ring, e.g. cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and cyclodecyl, where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, for example chloro-, dichloro- and trichlorocyclopropyl, fluoro-, difluoro- and trifluorocyclopropyl, chloro-, dichloro-, trichloro, tetrachloro-, pentachloro- and hexachlorocyclohexyl and the like.
  • Ci-C 10 -alkylcarbonyr refers to d-d o -alkyl which is bound to the remainder of the molecule via a carbonyl group.
  • Examples include CO-CH 3 , CO-C 2 H 5 , CO-CH 2 -C 2 H 5 , CO-CH(CH 3 ) 2 , n-butylcarbonyl, CO-CH(CHa)-C 2 H 5 , CO-CH 2 -CH(CHa) 2 , CO-C(CH 3 ) 3 , n-pentylcarbonyl, 1- methylbutylcarbonyl, 2-methylbutylcarbonyl, 3-methylbutylcarbonyl, 2,2- dimethylpropylcarbonyl, 1-ethylpropylcarbonyl, n-hexylcarbonyl, 1 ,1- dimethylpropylcarbonyl, 1 ,2-dimethylpropylcarbonyl, 1-methylpentylcarbonyl, 2- methylpentylcarbon
  • d-C 10 -alkoxycarbonyl refers to Ci-C 10 -alkoxy which is bound to the remainder of the molecule via a carbonyl group.
  • Examples include CO-OCH 3 , CO-OC 2 H 5 , CO-OCH 2 -C 2 H 5 , CO-OCH(CH 3 ) 2 , n-butoxycarbonyl, CO-OCH(CHa)-C 2 H 5 , CO-OCH 2 -CH(CHa) 2 , CO-OC(CH 3 ) 3 , n-pentoxycarbonyl, 1- methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 2,2- dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, n-hexoxycarbonyl, 1 ,1- dimethylpropoxycarbonyl, 1 ,2-dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl, 2- methylpentoxycarbonyl, 3-methyl
  • halo-Ci-C 10 -alkoxycarbonyl refers to d-Cio-haloalkoxy which is bound to the remainder of the molecule via a carbonyl group.
  • hydroxy-C r C 10 -alkyr refers to d-do-alkyl, as defined herein, in particular to methyl, ethyl, 1 -propyl or 2-propyl, which is substituted by one radical selected from hydroxy, d-C 10 -alkoxy, C 1 -Ci 0 - haloalkoxy, CrC 10 -alkoxycarbonyl or Ci-C 10 -haIoalkoxycarbonyl.
  • the term "5- or 6-membered heterocyclic radical with 1 , 2, 3 or 4 heteroatoms which are selected, independently of one another, from O, N and S" comprises monocyclic 5- or 6-membered heteroaromatic rings and nonaromatic saturated or partially unsaturated 5- or 6-membered mono-heterocycles, which carry 1 , 2, 3, or 4 heteroatoms as ring members.
  • the heterocyclic radical may be attached to the remainder of the molecule via a carbon ring member or via a nitrogen ring member.
  • non-aromatic rings examples include pyrrolidinyl, pyrazolinyl, imidazolinyl, pyrrolinyl, pyrazolinyl, imidazolinyl, tetrahydrofuranyl, dihydrofuranyl, 1 ,3-dioxolanyl, dioxolenyl, thiolanyl, dihydrothienyl, oxazolidinyl, isoxazolidinyl, oxazolinyl, isoxazolinyl, thiazolinyl, isothiazolinyl, thiazolidinyl, isothiazolidinyl, oxathiolanyl, piperidinyl, piperazinyl, pyranyl, dihydropyranyl, tetrahydropyranyl, dioxanyl, thiopyranyl, dihydrothiopyranyl, tetrahydrothio
  • Examples for monocyclic 5- to 6-membered heteroaromatic rings include triazinyl, pyrazinyl, pyrimidyl, pyridazinyl, pyridyl, thienyl, furyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, thiazolyl, oxazolyl, thiadiazolyl, oxadiazolyl, isothiazolyl and isoxazolyl.
  • a in formula I is a cyclic radical selected from phenyl, thienyl, furyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazoloyl, pyridyl, pyrimidinyl, pyrazinyl, and pyridazinyl and where the cyclic radical may be unsubstituted or substituted as described above.
  • the aformentioned radicals are unsubstituted or substituted by 1, 2 or 3 radicals R a as defined above.
  • Preferred radicals R a comprise halogen, CN, Ci-C 4 -alkyl, CrC 4 -alkoxy, C 1 -C 4 - haloalkoxy, C r C 4 -alkylthio and Ci-C 4 -haloalkyl, in particular F, Cl, methyl, methoxy, ethoxy, methylthio, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, trifluoromethoxy and difluoromethoxy.
  • wherin A is a cyclic radical selected from phenyl, thienyl, furyl, isoxazolyl, pyrazolyl, imidazolyl, pyrazinyl, pyrimidinyl and pyridyl, in particular from pyridyl, thienyl and phenyl, where the cyclic radical may be substituted by 1 , 2 or 3 substuituents R a which are as defined above and which are preferably selected, independently of one another, from halogen, C 1 -C 4 - alkyl, C r C 4 -alkoxy, Ci-C 4 -haloalkoxy, Ci-C 4 -alkylthio and CrCrhaloalkyl, in particular from F, Cl, methyl, methoxy, ethoxy, methylthio, difluoromethyl, trifluoromethyl, 2,2,2- trifluoroethyl, trifluorome
  • Examples of preferred radicals A comprise: - 2-thienyl, 3-bromothien-2-yl, 4-bromothien-2-yl, 5-bromothien-2-yl, 4,5- dibromothien-2-yl, 3-chlorothien-2-yl, 4-chlorothien-2-yl, 5-chlorothien-2-yl, 3- chloro-4-methylthien-2-yl, 3-methylthien-2-yl, 4-methylthien-2-yl, 5-methylthien-2- yl, 3-methoxythien-2-yl, 3-methoxy-5-(trifluoromethyl)thien-2-yl, 3-ethoxy-5- (trifluoromethyl)thien-2-yl, 2-bromo-4,5-dimethylthien-2-yl, - pyridin-2-yl, 6-methylthiopyridin-2-yl, 3-fluoropyridin-2-yl, 3-methoxypyridin-2-yl, 6-methyl
  • the cyclic radical may also be napthyl, 1 ,2,3,4-tetrahydroisochinolin-3-yl, 2- benzothienyl, benzo[1 ,3]-dioxol-5-yl, indolyl or benzimidazolyl, where the cyclic radical may be unsubstituted or substituted as described above.
  • the aformentioned radicals are unsubstituted or substituted by 1 , 2 or 3 radicals R a as defined above. Examples of these radicals A comprise:
  • A is a 5- or 6-membered heterocyclic radical with 1 to 4 heteroatoms as ring members which are selected, independently of one another, from O, N and S and may also have a carbonyl group as ring member, and may have 1, 2, 3, 4 or 5 substituents R a as defined above.
  • a very preferred embodiment of the invention relates to compounds of the formula I 1 wherein A is thienyl, in particular 2-thienyl which is unsubstituted or substituted by 1 , 2 or 3 radicals R a as defined above, the radicals R a being preferably selected, independently of one another, from halogen, CrC 4 -alkyl, d-C 4 -alkoxy, CrC 4 -alkylthio, Ci-C 4 -haloalkoxy and CrC 4 -haloalkyl, in particular from F, Cl, Br, methyl, methoxy, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, trifluoromethoxy and difluoromethoxy.
  • A is furyl, in particular 2-furyl which is unsubstituted or substituted by 1, 2 or 3 radicals R a as defined above, the radicals R a being preferably selected, independently of one another, from halogen, C r C 4 -alkyl, C r C 4 -alkoxy, C r C 4 -alkylthio, CrC 4 -haloalkoxy and CrCVhaloalkyl, in particular from F, Cl, Br, methyl, methoxy, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, trifluoromethoxy and difluoromethoxy.
  • A is pyridyl, in particular 2- or 3-pyridyl, more preferably 2-pyridyl which is unsubstituted or substituted by 1, 2 or 3 radicals R a as defined above, the radicals R a being preferably selected, independently of one another, from halogen, Cr C 4 -alkyl, C 1 -C ⁇ aIkOXy, C r C 4 -alkylthio, C r C 4 -haloalkoxy and C 1 -C 4 -haloalkyl, in particular from F, Cl, Br, methyl, methoxy, difluoromethyl, trifluoromethyl, 2,2,2- trifluoroethyl, trifluoromethoxy and difluoromethoxy.
  • a further very preferred embodiment of the invention relates to compounds of the formula I, wherein A is phenyl, which is unsubstituted or substituted by 1, 2 or 3 radicals R a as defined above, the radicals R a being preferably selected, independently of one another, from halogen, Ci-C 4 -alkyl, CrC 4 -alkoxy, Ci-C 4 -haloalkoxy, C 1 -C 4 - alkylthio and C r C 4 -haloalkyl, in particular from F, Cl, Br 1 methyl, methoxy, ethoxy, methylthio, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, trifluoromethoxy and difluoromethoxy.
  • Q is preferably selected from the group consisting of a single bond, -CH 2 -, -CH 2 -CH 2 -, -0-CH 2 -, -0-CH 2 -CH 2 -, 0-CH 2 -CH 2 -CH 2 -, -NH-CH 2 -CH 2 -, -NH-C(O)-CH 2 -, -S-CH 2 -, -S-CH 2 -CH 2 -, -0-CH(CH 3 )- and -S-CH(CH 3 )-, in particular from a single bond, -CH 2 -, -0-CH 2 -, -S-CH 2 -, -0-CH(CH 3 )- and -S-CH(CH 3 )-.
  • the heteroatom of Q is preferably attached to A. More preferably Q is a single bond or -CH 2 -.
  • Preferred examples of the moiety A-Q include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, 4-hydroxybutyl, 5- hydroxypentyl, 2,2-dimethoxyethyl, 2,2-diethoxyethyl, methoxycarbonylmethyl or ethoxycarbonylmethyl, especially methyl.
  • R 1 is H, CrC 10 -alkyl, d-C 10 -haloalkyl, C 3 -C 10 - cycloalkyl, C 3 -C 1o -halocycloalkyl, C 2 -C 10 -alkenyl, C 2 -C 1o -haloalkenyl, C 2 -C 10 -alkynyl and C 2 -C 10 -haloalkynyl.
  • R 1 is preferably hydrogen, CrC ⁇ -alkyl, C 1 -C 10 - haloalkyl, more preferably hydrogen, C r C 4 -alkyl or C r C 4 -haloalkyl, and especially hydrogen.
  • R 1 is selected from the group consisting of phenyl and a 5- or 6-membered heterocyclic radical with 1 to 4 heteroatoms which are selected, independently of one another, from O, N and S 1 it being possible for phenyl and the 5- or 6-membered heterocyclic radical to be unsubstituted or substituted by 1 , 2, 3, 4 or 5 substituents R a as defined above.
  • R 1 is pyridyl, in particular 3- pyridyl, C 3 -C 10 -cycloalkyl, phenyl and more preferably C 3 -C 6 -Cy clop ropy I
  • R 2 is preferably selected from hydrogen, halogen and Ci-C 4 -alkyl, in particular from hydrogen, fluorine chlorine, bromine, methyl or ethyl.
  • R 3 is preferably selected from hydrogen, halogen and CrC 4 -alkyl, with hydrogen being more preferred.
  • R 5 is preferably selected from hydrogen, Ci-Ci ⁇ -alkyl, C r C 1o -haloalkyl, C 3 -Ci 0 - cycloalkyl, C 3 -C 10 -halocycloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -haloalkenyl, in particular from hydrogen and Ci-C 4 -alkyl.
  • R 6 is selected from the group consisiting of H, CrCi O -alkyl, which is optionally substituted by CN or NO 2 , C r Ci 0 -haloalkyl, C 3 -C 10 -cycloalkyl, C 3 - C 1o -halocycloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -haloalkenyl, C 2 -C 10 -alkynyl, C 2 -Ci 0 - haloalkynyl, CrCio-alkylsulfinyl, Ci-Cio-haloalkylsulfinyl, Ci-Ci 0 -alkylsulfonyl, C 1 -C 10 - haloalkylsulfonyl, C r Ci 0 -alkoxycarbonyl, d-Cio-haloalkoxycarbonyl, C 2 r Ci 0
  • R 6 is preferably hydrogen, C r C 4 - alkyl, d-C ⁇ haloalkyl, C r C 4 -alkylsulfonyl, C r C 4 -alkylcarbonyl, C r C 4 -alkylsulfonyl or Ci-C 4 -haloalkylsulfonyl, in particular hydrogen.
  • R 6 is CrCi ⁇ -alkylthio, Ci-C 1o -haloalkylthio, CrCio-alkylcarbonyl, where the alkyl moiety of alkylcarbonyl is substituted by 1 , 2 or 3 substituents selected from the group consisting of C r Ci 0 - alkylthio, phenylthio, phenyl and phenoxy, benzoyl (C 6 H 5 -CO-), C 3 -Cio-cycloalkylcarbonyl, R 6a -CO-, wherein R 6a is C r C 4 -alkoxycarbonyl, phenoxy, naphthyl or a 5- or 6-membered heterocyclic radical with 1 to 4 heteroatoms which are selected, independently of one another, from O, N and S, it being possible for phenoxy, naphthyl and the 5- or 6-membered heterocyclic radical to be unsubsti
  • R 6 is preferably Ci-C 4 -alkylcarbonyI, wherein the alkyl moiety of alkylcarbonyl is substituted by a radical selected from phenyl, C r C 4 -alkylthio, phenylthio and phenoxy, such as phenoxymethylcarbonyl, 2-methylsulfanylethylcarbonyl and phenylsulfanylmethylcarbonyl or benzoyl.
  • R 6 is a benzoyl or a radical of the formula R 6a -C(0)-, wherein R 6a is C r C 2 -alkoxycarbonyl, phenoxy, a 5- or 6-membered aromatic heterocyclic radical with 1 or 2 heteroatoms which are selected, independently of one another, from O, N and S, it being possible for the 5- or 6-membered heterocyclic radical to be unsubstituted or substituted by 1 or 2 substituents R a as defined above.
  • R 6a are phenoxy, 3-isoxazolyl, 5-isoxazolyl, 2-thienyl and 2-furyl and methoxycarbonyl.
  • Ar is preferably phenyl, which is unsubstituted or substituted by 1 , 2, 3 or 4, in particular 1 , 2 or 3 radicals R c as defined above.
  • R 4 is one of the 1 to 4 radicals R c as defined above or R 4 together with R 2 is the aformentioned bivalent radical.
  • Ar is an aromatic radical selected from phenyl, naphthyl, pyridyl, pyrimidyl, furyl and thienyl and wherein two radicals R c which are bound to adjacent carbon atoms may form a 0-CH 2 -O moiety, where in said moiety 1 or 2 hydrogen atoms may be replaced by a radical R b as defined above.
  • the radical R c is halogen, cyano, nitro, Ci-C 10 -alkyl, C 1 -Ci 0 - haloalkyl, C 3 -Ci 0 -cycloalkyl, C 3 -C 10 -halocycloalkyl, C 2 -Ci 0 -alkenyl, C 2 -C 10 -haloalkenyl, C 2 -C 10 -alkynyl, C 3 -C 1o -haloalkynyl, d-C ⁇ -alkoxy, C r C 1o -haloalkoxy, C 2 -C 10 -alkenyloxy, C 2 -Ci 0 -alkynyloxy, C 3 -C 1o -haloalkynyloxy, C r C 1o -alkylthio, C r C 1o -haloalkylthio, C 1 -C 10 - alkyls
  • the radicals R c are selected, independently of one another, from halogen, CN, Ci-C 4 -alkyl, C r C 4 -alkoxy, C ⁇ C ⁇ haloalkoxy and Ci-C 4 -haloalkyl, more preferably F, Cl, CN, C r C 3 -alkoxy, in particular methoxy, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy and methyl.
  • the radical R c is C r C 1o -alkylcarbonyl.
  • a further very preferred embodiment of the invention relates to compounds of the formula I, wherein Ar is furyl, in particular 2-furyl which is unsubstituted or substituted by 1 radical R c as defined above or thienyl, in particular 2-thienyl, which may be unsubstituted or substituted by 1 radical R c as defined above.
  • the radical R 2 in formula I is a monovalent radical, i.e. R 2 and R 4 together do not form a bivalent radical.
  • R 2 is preferably selected from hydrogen, halogen, CrC 4 -alkyl, C r C 4 -alkoxy, C 1 -C 4 - haloalkoxy and C r C 4 -haloalkyl. More preferably R 2 is hydrogen, fluorine, chlorine bromine, methyl or ethyl.
  • R 4 is hydrogen or a radical R c as defined above, in particular hydrogen.
  • Ar in formula I is preferably phenyl, which is unsubstituted or substituted by 1, 2, 3 or 4, in particular 1, 2 or 3 radicals R c as defined above.
  • Ar in formula I is preferably phenyl, which is unsubstituted or substituted by 1 , 2 or 3, in particular O, 1 or 2 radicals R c as defined above.
  • R b is preferably selected from halogen, Ci-C 4 -alkyl, C r C 4 -alkoxy, C 1 - C 4 -haloalkoxy and C r C 4 -haloalkyl.
  • R 7 , R 8 are preferably selected independently from one another from hydrogen and C r C 4 -alkyl.
  • R 9 is preferably selected from hydrogen, C r C 4 -alkyl and C 1 -C 4 - alkylcarbonyl, in particular hydrogen.
  • R 10 is preferably selected from hydrogen, halogen and C 1 -C 4 ⁇ yI, in particular hydrogen.
  • R 11 , R 12 are preferably selected independently from one another from hydrogen and C r C 4 -alkyl, in particular hydrogen.
  • R 13 is preferably selected from hydrogen and CrC 4 -alkyl, in particular hydrogen.
  • k is O 1 1, 2 or 3, and wherein A, Q, R 1 , R 2 , R 3 , R 5 and R c are as defined above. Amongst the compounds Ia those are preferred, wherein Q, A, R 1 , R 2 , R 3 , R 5 and R c have the meanings given as preferred.
  • Table 10 Compounds of the formula Ia, wherein R 1 is H, R 3 is H, R 2 is H, R 5 is H and (R c ) k is 2-F and wherein Q and A are given in table A;
  • Table 15 Compounds of the formula Ia, wherein R 1 is H, R 3 is H, R 2 is H, R 5 is H and (R c ) k is 2- OCHF 2 and wherein Q and A are given in table A;
  • Table 19 Compounds of the formula Ia, wherein R 1 is H, R 3 is H, R 2 is F, R 5 is H and (R c ) k is 3- fluoro and wherein Q and A are given in table A;
  • Table 20 Compounds of the formula Ia, wherein R 1 is H 1 R 3 is H 1 R 2 is F, R 5 is H and (R c ) k is 3- difluoromethoxy and wherein Q and A are given in table A;
  • Table 25 Compounds of the formula Ia, wherein R 1 is H 1 R 3 is H, R 2 is F, R 5 is H and (R c ) k is 2-F and wherein Q and A are given in table A;
  • Table 29 Compounds of the formula Ia, wherein R 1 is H, R 3 is H, R 2 is F, R 5 is H and (R c ) k is A- OCH 3 and wherein Q and A are given in table A;
  • Table 30 Compounds of the formula Ia, wherein R 1 is H, R 3 is H, R 2 is F, R 5 is H and (R c ) k is 2- OCHF 2 and wherein Q and A are given in table A;
  • Table 35 Compounds of the formula Ia, wherein R 1 is H, R 3 is H, R 2 is Cl, R 5 is H and (R c ) k is 3- difluoromethoxy and wherein Q and A are given in table A;
  • Table 39 Compounds of the formula Ia, wherein R 1 is H, R 3 is H, R 2 is Cl, R 5 is H and (R c ) k is A- methylthio-3-trifluoromethyl and wherein Q and A are given in table A;
  • Table 40 Compounds of the formula Ia, wherein R 1 is H, R 3 is H, R 2 is Cl, R 5 is H and (R c ) k is 2-F and wherein Q and A are given in table A;
  • Table 45 Compounds of the formula Ia, wherein R 1 is H, R 3 is H, R 2 is Cl, R 5 is H and (R c ) k is 2- OCHF 2 and wherein Q and A are given in table A;
  • Table 49 Compounds of the formula Ia, wherein R 1 is H, R 3 is H, R 2 is B, R 5 is H r and (R c ) k is 3- fluoro and wherein Q and A are given in table A;
  • Table 50 Compounds of the formula Ia 1 wherein R 1 is H, R 3 is H 1 R 2 is Br, R 5 is H and (R c ) k is 3- difluoromethoxy and wherein Q and A are given in table A;
  • Table 55 Compounds of the formula Ia 1 wherein R 1 is H, R 3 is H, R 2 is Br, R 5 is H and (R c ) k is 2-F and wherein Q and A are given in table A;
  • Table 59 Compounds of the formula Ia, wherein R 1 is H, R 3 is H 1 R 2 is Br, R 5 is H and (R c ) k is 4- OCH 3 and wherein Q and A are given in table A;
  • Table 60 Compounds of the formula Ia, wherein R 1 is H, R 3 is H, R 2 is Br, R 5 is H and (R c ) k is 2- OCHF 2 and wherein Q and A are given in table A;
  • Table 65 Compounds of the formula Ia, wherein R 1 is H, R 3 is H, R 2 is CH 3 , R 5 is H and (R c ) k is 3-difluoromethoxy and wherein Q and A are given in table A;
  • Table 69 Compounds of the formula Ia, wherein R 1 is H, R 3 is H, R 2 is CH 3 , R 5 is H and (R c ) k is 4-methylthio-3-trifluoromethyl and wherein Q and A are in given table A.
  • Table 70 Compounds of the formula Ia, wherein R 1 is H, R 3 is H, R 2 is CH 3 , R 5 is H and (R c ) k is 2-F and wherein Q and A are given in table A;
  • Table 75 Compounds of the formula Ia, wherein R 1 is H, R 3 is H, R 2 is CH 3 , R 5 is H and (R c ) k is 2-OCHF 2 and wherein Q and A are given in table A;
  • Table 79 Compounds of the formula Ia, wherein R 1 is H, R 3 is H, R 2 is CH 2 CH 3 , R 5 is H and (R c ) k is 3-fluoro and wherein Q and A are given in table A;
  • Table 80 Compounds of the formula Ia, wherein R 1 is H, R 3 is H, R 2 is CH 2 CH 3 , R 5 is H and (R c ) k is 3-difluoromethoxy and wherein Q and A are given in table A;
  • Table 85 Compounds of the formula Ia, wherein R 1 is H, R 3 is H, R 2 is CH 2 CH 3 , R 5 is H and (R c ) k is 2-F and wherein Q and A are given in table A;
  • Table 89 Compounds of the formula Ia 1 wherein R 1 is H, R 3 is H, R 2 is CH 2 CH 3 , R 5 is H and (R c ) k is 4-OCH 3 and wherein Q and A are given in table A;.
  • Table 90 Compounds of the formula Ia, wherein R 1 is H, R 3 is H, R 2 is CH 2 CH 3 , R 5 is H and (R c ) k is 2-OCHF 2 and wherein Q and A are given in table A;
  • k is 0, 1 , 2 or 3, and wherein A, Q, R 1 , R 3 , R 5 and R c are as defined above and Y is as defined above.
  • Y is O, OCH 2 or S and wherein Q, A, R 1 , R 3 , R 5 and R c have the meanings given as preferred.
  • Table 367 Compounds of the formula Ia 1 wherein Y is O 1 R 1 is H, R 3 is H, R 5 is CH 3 and (R c ) k is A- Cl and wherein Q and A are given in table A;
  • Table 372 Compounds of the formula Ia, wherein Y is S 1 R 1 is H, R 3 is H, R 5 is CH 3 and (R c ) k is A- Cl, 5-NO 2 and wherein Q and A are given in table A;
  • the compounds of the formula I may be readily synthesized using techniques generally known by synthetic organic chemists.
  • individual compounds I are not obtainable by the route described above, they can be prepared by derivatization of other compounds I or by customary modifications of the synthesis routes described.
  • the preparation of the compounds of formula I may lead to them being obtained as isomer mixtures (stereoisomers, enantiomers). If desired, these can be resolved by the methods customary for this purpose, such as crystallization or chromatography, also on optically active adsorbate, to give the pure isomers.
  • Acyl hydrazones of the formula Il are known in the art, e.g. from PCT/EP 2004/005681 , or they can be obtained applying synthesis methods described for example in WO 87/06133 by analogy.
  • suitable hydrazides III can be reacted with aldehydes, esters or ketones IV according to scheme 3 to form acyl hydrazones of the formula II.
  • the compounds of formula I are effective through contact (via soil, glass, wall, bed net, carpet, plant parts or animal parts), and/or ingestion (bait, or plant part).
  • the compounds of the formula I are in particular suitable for efficiently controlling nematodes and insects. In particular, they are suitable for controlling the following pests:
  • beetles Coldoptera
  • Agrilus sinuatus for example Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceuthorrhynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Diabrotica Iongicornis, Diabrotica 12-punctata, Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis,
  • dipterans dipterans
  • Aedes aegypti Aedes vexans, Anastrepha ludens, Anopheles mac ⁇ lipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Contarinia sorghicola, Cordylobia anthropophaga, Culex pipiens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Fannia canicularis, Gasterophilus intestinalis, Glossina morsitans, Haematobia irritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineata, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, May
  • Thrips e.g. Dichromothrips spp., Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci,
  • Hymenopterans e.g. Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata and Solenopsis invicta,
  • Heteroptera e.g. Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubea insularis and Thyanta perditor,
  • homopterans e.g. Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis forbesi, Aphis pomi, Aphis gossypii, Aphis grossulariae, Aphis schneideri, Aphis spiraecola, Aphis sambuci, Acyrthosiphon pisum, Aulacorthum solani, Bemisa tabaci, Bemisa argentifolii, Brachycaudus cardui, Brachycaudus helichrysi, Brachycaudus persicae, Brachycaudus prunicola, Brevicoryne brassicae, Capitophorus horni, Cerosipha gossypii, Chaetosiphon fragaefolii, Cryptomyzus ribis, Dreyfusia nordmannianae
  • Isoptera e.g. Calotermes flavicollis, Leucotermes flavipes, Reticulitermes lucifugus und Termes natalensis, and
  • orthopterans e.g. Acheta domestica, Blatta orientalis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femur-rubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Periplaneta americana, Schistocerca ameri- cana, Schistocerca peregrina, Stauronotus maroccanus and Tachycines asynamorus;
  • Orthoptera e.g. Acheta domestica, Blatta orientalis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femur-rubrum, Melan
  • plant parasitic nematodes such as root knot nematodes, Meloidogyne hapla, Meloido- gyne incognita, Meloidogyne javanica, and other Meloidogyne species; cyst-forming nematodes, Globodera rostochiensis and other Globodera species; Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, and other Heterode- ra species; Seed gall nematodes, Anguina species; Stem and foliar nematodes, Aphe- lenchoides species; Sting nematodes, Belonolaimus longicaudatus and other Belono- laimus species; Pine nematodes, Bursaphelenchus xylophilus and other Bursaphelen- chus species; Ring nematodes, Criconema species
  • the compounds of the formula I and their salts are also useful for controlling arachnids (Arachnoidea), such as acarians (Acarina), e.g. of the families Argasidae, Ixodidae and Sarcoptidae, such as Amblyomma americanum, Amhlyomma variegatum, Argas persi- cus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Dermacentor silvarum, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus mou- bata, Otobius megnini, Dermanyssus gallinae, Psoroptes ovis, Rhipicephal ⁇ s appendi- culatus, Rhipicephalus evertsi, Sarcoptes scabiei, and Eriophyidae spp.
  • arachnoidea
  • Tetranychidae spp. such as Tetranych ⁇ s cinnaba ⁇ nus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius and Tetranychus urticae, Panonychus ulmi, Panonychus citri, and oligonychus pratensis.
  • the compounds I can be converted into the customary formulations, e.g. solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • the use form depends on the particular purpose; it is intended to ensure in each case a fine and uniform distribution of the compound according to the invention.
  • the formulations are prepared in a known manner, e.g. by extending the active ingredient with solvents and/or carriers, if desired using emulsifiers and dispersants.
  • Solvents/auxiliaries which are suitable, are essentially:
  • aromatic solvents for example Solvesso products, xylene
  • paraffins for example mineral fractions
  • alcohols for example methanol, butanol, pentanol, benzyl alcohol
  • ketones for example cyclohexanone, gamma-butyrolactone
  • pyrrolidones NMP, NOP
  • acetates glycols, fatty acid dimethylamides, fatty acids and fatty acid esters.
  • solvent mixtures may also be used.
  • carriers such as ground natural minerals (e.g. kaolins, clays, talc, chalk) and ground synthetic minerals (e.g.
  • emulsifiers such as nonionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates) and dispersants such as lignin-sulfite waste liquors and methylcellulose.
  • Suitable surfactants are alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, furthermore condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenyl ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenyl polyglycol ethers, tributylpheny
  • Substances which are suitable for the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions are mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strongly polar solvents, for example dimethyl sulfoxide, N-methylpyrrolidone and water.
  • mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example toluene, xylene, paraffin
  • Powders, materials for spreading and dusts can be prepared by mixing or concomitantly grinding the active substances with a solid carrier.
  • Granules for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers.
  • solid carriers are mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as, for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.
  • mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth
  • the formulations comprise from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the active ingredient.
  • the active ingredients are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
  • a compound according to the invention 20 parts by weight of a compound according to the invention are dissolved in cyclohexanone with addition of a dispersant, for example polyvinylpyrrolidone. Dilution with water gives a dispersion.
  • a dispersant for example polyvinylpyrrolidone
  • a compound according to the invention 40 parts by weight of a compound according to the invention are dissolved in xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5% strength).
  • This mixture is introduced into water by means of an emulsifier (Ultraturrax) and made into a homogeneous emulsion. Dilution with water gives an emulsion.
  • a compound according to the invention in an agitated ball mill, 20 parts by weight of a compound according to the invention are milled with addition of dispersant, wetters and water or an organic solvent to give a fine active ingredient suspension. Dilution with water gives a stable suspension of the active ingredient.
  • Water-dispersible granules and water-soluble granules (WG, SG) 50 parts by weight of a compound according to the invention are ground finely with addition of dispersants and wetters and made into water-dispersible or water-soluble granules by means of technical appliances (for example extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active ingredient.
  • Water-dispersible powders and water-soluble powders (WP, SP) 75 parts by weight of a compound according to the invention are ground in a rotor- stator mill with addition of dispersant, wetters and silica gel. Dilution with water gives a stable dispersion or solution with the active ingredient.
  • a compound according to the invention is ground finely and associated with 95.5% carriers.
  • Current methods are extrusion, spray drying or the fluidized bed. This gives granules to be applied undiluted.
  • the active ingredients can be used as such, in the form of their formulations or the use forms prepared therefrom, eg. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dustable products, materials for spreading, or granules, by means of spraying, atomizing, dusting, spreading or pouring.
  • the use forms depend entirely on the intended purposes; it is intended to ensure in each case the finest possible distribution of the active ingredients according to the invention.
  • Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions) by adding water.
  • emulsions, pastes or oil dispersions the substances, as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetter, tackifier, dispersant or emulsifier.
  • concentrates composed of active substance, wetter, tackifier, dispersant or emulsifier and, if appropriate, solvent or oil and such concentrates are suitable for dilution with water.
  • the active ingredient concentrations in the ready-to-use products can be varied within relatively wide ranges. In general, they are from 0.0001 to 10%, preferably from 0.01 to 1%.
  • the active ingredients may also be used successfully in the ultra-low-volume process (ULV), it being possible to apply formulations comprising over 95% by weight of active ingredient, or even to apply the active ingredient without additives.
  • UUV ultra-low-volume process
  • compositions of this invention may also contain other active ingredients, for example other pesticides, insecticides, herbicides, fertilizers such as ammonium nitrate, urea, potash, and superphosphate, phytotoxicants and plant growth regulators, safeners and nematicides.
  • additional ingredients may be used sequentially or in combination with the above-described compositions, if appropriate also added only immediately prior to use (tank mix).
  • the plant(s) may be sprayed with a composition of this invention either before or after being treated with other active ingredients.
  • These agents usually are admixed with the agents according to the invention in a weight ratio of 1 :100 to 100:1.
  • Organophosphates Acephate, Azinphos-methyl, Chlorpyrifos, Chlorfenvinphos, Diazinon, Dichlorvos, Dicrotophos, Dimethoate, Disulfoton, Ethion, Fenitrothion, Fenthion, Isoxathion, Malathion, Methamidophos, Methidathion, Methyl-Parathion, Mevinphos, Monocrotophos, Oxydemeton-methyl, Paraoxon, Parathion, Phenthoate, Phosalone, Phosmet, Phosphamidon, Phorate, Phoxim, Pirimiphos-methyl, Profenofos, Prothiofos, Sulprophos, Tetrachlorvinphos, Terbufos, Triazophos, Trichlorfon;
  • Pyrethroids Bifenthrin, Cyfluthrin, Cypermethrin, alpha-Cypermethrin, Deltamethrin, Esfenvalerate, Ethofenprox, Fenpropathrin, Fenvalerate, Cyhalothrin, Lambda- Cyhalothrin, Permethrin, Silafluofen, Tau-Fluvalinate, Tefluthrin, Tralomethrin, Zeta- Cypermethrin;
  • Arthropod growth regulators a) chitin synthesis inhibitors: benzoylureas: Chlorfluazuron, Diflubenzuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron, Teflubenzuron, Triflumuron; Buprofezin, Diofenolan, Hexythiazox, Etoxazole, Clofentazine; b) ecdysone antagonists: Halofenozide, Methoxyfenozide, Tebufenozide; c) juvenoids: Pyriproxyfen, Methoprene, Fenoxycarb; d) lipid biosynthesis inhibitors: Spirodiclofen;
  • Fungicides are those selected from the group consisting of
  • acylalanines such as benalaxyl, metalaxyl, ofurace, oxadixyl,
  • amine derivatives such as aldimorph, dodine, dodemorph, fenpropimorph, fenpropidin, guazatine, iminoctadine, spiroxamin, tridemorph
  • anilinopyrimidines such as pyrimethanil, mepanipyrim or cyrodinyl
  • antibiotics such as cycloheximid, griseofulvin, kasugamycin, natamycin, polyoxin or streptomycin
  • azoles such as bitertanol, bromoconazole, cyproconazole, difenoconazole, dinitroconazole, epoxiconazole, fenbuconazole, fluquiconazole, flusilazole, hexaconazole, imazalil, metconazole, myclobutanil, penconazole, propiconazole, prochloraz, prothioconazole, tebuconazole, triadimefon, triadimenol, triflumizol, triticonazole, flutriafol
  • dicarboximides such as iprodion, myclozolin, procymidon, vinclozolin,
  • dithiocarbamates such as ferbam, nabam, maneb, mancozeb, metam, metiram, propineb, polycarbamate, thiram, ziram, zineb, • heterocyclic compounds such as anilazine, benomyl, boscalid, carbendazim, carboxin, oxycarboxin, cyazofamid, dazomet, dithianon, famoxadon, fenamidon, fenarimol, fuberidazole, flutolanil, furametpyr, isoprothiolane, mepronil, nuarimol, probenazole, proquinazid, pyrifenox, pyroquilon, quinoxyfen, silthiofam, thiabendazole, thifluzamid, thiophanate-methyl, tiadinil, tricyclazole, triforine, • copper fungicides such as Bordeaux mixture, copper acetate, copper
  • nitrophenyl derivatives such as binapacryl, dinocap, dinobuton, nitrophthalisopropyl
  • phenylpyrroles such as fenpiclonil or fludioxonil
  • strobilurins such as azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin or trifloxystrobin, • sulfenic acid derivatives such as captafol, captan, dichlofluanid, folpet, tolylfluanid
  • compositions are particularly useful for protecting plants against infestation of said pests or to combat these pests in infested plants.
  • the compounds of formula I are also suitable for the treatment of seeds.
  • compositions for seed treatments include for example flowable concentrates FS, solutions LS, powders for dry treatment DS, water dispersible powders for slurry treatment WS, water soluble powders SS and emulsion ES.
  • Application to the seeds is carried out before sowing, either directly on the seeds or after having pregerminated the latter.
  • Preferred FS formulations of compounds of formula I for seed treatment usually comprise from 0.5 to 80% of the active ingredient, from 0,05 to 5 % of a wetter, from 0.5 to 15 % of a dispersing agent, from 0,1 to 5 % of a thickener, from 5 to 20 % of an anti-freeze agent, from 0,1 to 2 % of an anti-foam agent, from 1 to 20 % of a pigment and/or a dye, from 0 to 15 % of a sticker /adhesion agent, from 0 to 75 % of a filler/vehicle, and from 0,01 to 1 % of a preservative.
  • Suitable pigments or dyes for seed treatment formulations are pigment blue 15:4, pigment blue 15:3, pigment blue 15:2, pigment blue 15:1 , pigment blue 80, pigment yellow 1 , pigment yellow 13, pigment red 112, pigment red 48:2, pigment red 48:1, pigment red 57:1, pigment red 53:1 , pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51, acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108.
  • Suitable adhesives are block copolymers EO/PO surfactants but also polyvinylalcohols, polyvinylpyrrolidones, polyacrylates, polymethacrylates, polybutenes, polyisobutylenes, polystyrene, polyethyleneamines, polyethyleneamides, polyethyleneimines (Lupasol®, Polymin®), polyethers and copolymers derived from these polymers.
  • Compositions which are useful for seed treatment are e.g.:
  • a Soluble concentrates (SL, LS)
  • compounds of formula I are preferably used in a bait composition.
  • the bait can be a liquid, a solid or a semisolid preparation (e.g. a gel).
  • Solid baits can be formed into various shapes and forms suitable to the respective application e.g. granules, blocks, sticks, disks.
  • Liquid baits can be filled into various devices to ensure proper application, e.g. open containers, spray devices, droplet sources, or evaporation sources.
  • Gels can be based on aqueous or oily matrices and can be formulated to particular necessities in terms of stickyness, moisture retention or aging characteristics.
  • the bait employed in the composition is a product which is sufficiently attractive to incite insects such as ants, termites, wasps, flies, mosquitos, crickets etc. or cockroaches to eat it.
  • the attractiveness can be manipulated by using feeding stimulants or sex pheromones.
  • Food stimulants are chosen, for example, but not exclusively, from animal and/or plant proteins (meat-, fish- or blood meal, insect parts, egg yolk), from fats and oils of animal and/or plant origin, or mono-, oligo- or polyorganosaccharides, especially from sucrose, lactose, fructose, dextrose, glucose, starch, pectin or even molasses or honey.
  • Fresh or decaying parts of fruits, crops, plants, animals, insects or specific parts thereof can also serve as a feeding stimulant.
  • Sex pheromones are known to be more insect specific. Specific pheromones are described in the literature and are known to those skilled in the art.
  • Formulations of compounds of formula I as aerosols are highly suitable for the non-professional user for controlling pests such as flies, fleas, ticks, mosquitos or cockroaches.
  • Aerosol recipes are preferably composed of the active compound, solvents such as lower alcohols (e.g. methanol, ethanol, propanol, butanol), ketones (e.g. acetone, methyl ethyl ketone), paraffin hydrocarbons (e.g.
  • kerosenes having boiling ranges of approximately 50 to 250 0 C 1 dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, aromatic hydrocarbons such as toluene, xylene, water, furthermore auxiliaries such as emulsifiers such as sorbitol monooleate, oleyl ethoxylate having 3-7 mol of ethylene oxide, fatty alcohol ethoxylate, perfume oils such as ethereal oils, esters of medium fatty acids with lower alcohols, aromatic carbonyl compounds, if appropriate stabilizers such as sodium benzoate, amphoteric surfactants, lower epoxides, triethyl orthoformate and, if required, propellants such as propane, butane, nitrogen, compressed air, dimethyl ether, carbon dioxide, nitrous oxide, or mixtures of these gases.
  • emulsifiers such as sorbitol monooleate, oleyl ethoxylate having 3-7 mol of
  • the oil spray formulations differ from the aerosol recipes in that no propellants are used.
  • the compounds of formula I and its respective compositions can also be used in mosquito and fumigating coils, smoke cartridges, vaporizer plates or long-term vaporizers and also in moth papers, moth pads or other heat-independent vaporizer systems.
  • Methods to control infectious diseases transmitted by insects e.g. malaria, dengue and yellow fever, lymphatic filariasis, and leishmaniasis
  • compounds of formula I and its respective compositions also comprise treating surfaces of huts and houses, air spraying and impregnation of curtains, tents, clothing items, bed nets, tsetse-fly trap or the like, lnsecticidal compositions for application to fibers, fabric, knitgoods, nonwovens, netting material or foils and tarpaulins preferably comprise a mixture including the insecticide, optionally a repellent and at least one binder.
  • Suitable repellents for example are N,N-diethyl-meta-toluamide (DEET), N 1 N- diethylphenylacetamide (DEPA), 1-(3-cyclohexan-1-yl-carbonyl)-2-methylpiperine, (2- hydroxymethylcyclohexyl) acetic acid lactone, 2-ethyl-1 ,3-hexandiol, indalone, Methylneodecanamide (MNDA), a pyrethroid not used for insect control such as ⁇ (+/-)- 3-allyl-2-methyl-4-oxocyclopent-2-(+)-enyl-(+)-trans-chrysantemate (Esbiothrin), a repellent derived from or identical with plant extracts like limonene, eugenol, (+)- Eucamalol (1), (-)-i-epi-eucamalol or crude plant extracts from plants like Eucalyp
  • Suitable binders are selected for example from polymers and copolymers of vinyl esters of aliphatic acids (such as such as vinyl acetate and vinyl versatate), acrylic and methacrylic esters of alcohols, such as butyl acrylate, 2-ethylhexylacrylate, and methyl acrylate, mono- and di-ethylenically unsaturated hydrocarbons, such as styrene, and aliphatic diens, such as butadiene.
  • vinyl esters of aliphatic acids such as such as vinyl acetate and vinyl versatate
  • acrylic and methacrylic esters of alcohols such as butyl acrylate, 2-ethylhexylacrylate, and methyl acrylate
  • mono- and di-ethylenically unsaturated hydrocarbons such as styrene
  • aliphatic diens such as butadiene.
  • the impregnation of curtains and bednets is mostly done by dipping the textile material into emulsions or dispersions of the insecticide or spraying them onto the nets.
  • the compounds of formula I and its compositions can be used for protecting non-living material, in particular cellulose-based materials such as wooden materials e.g. trees, board fences, sleepers, etc. and buildings such as houses, outhouses, factories, but also construction materials, furniture, leathers, fibers, vinyl articles, electric wires and cables etc. from ants and/or termites, and for controlling ants and termites from doing harm to crops or human being (e.g. when the pests invade into houses and public facilities).
  • cellulose-based materials such as wooden materials e.g. trees, board fences, sleepers, etc. and buildings such as houses, outhouses, factories, but also construction materials, furniture, leathers, fibers, vinyl articles, electric wires and cables etc. from ants and/or termites, and for controlling ants and termites from doing harm to crops or human being (e.g. when the pests invade into houses and public facilities).
  • the compounds of formula I are applied not only to the surrounding soil surface or into the under-floor soil in order to protect wooden materials but it can also be applied to lumbered articles such as surfaces of the under-floor concrete, alcove posts, beams, plywoods, furniture, etc., wooden articles such as particle boards, half boards, etc. and vinyl articles such as coated electric wires, vinyl sheets, heat insulating material such as styrene foams, etc.
  • the ant controller of the present invention is applied to the crops or the surrounding soil, or is directly applied to the nest of ants or the like.
  • the pests are controlled by contacting the target parasite/pest, its food supply, habitat, breeding ground or its locus with a pesticidally effective amount of compounds of formula I or with a salt thereof or with a composition, containing a pesticidally effective amount of a compound of formula I or a salt thereof.
  • “Locus” means a habitat, breeding ground, plant, seed, soil, area, material or environment in which a pest or parasite is growing or may grow.
  • pesticidally effective amount means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism.
  • the pesticidally effective amount can vary for the various compounds/compositions used in the invention.
  • a pesticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired pesticidal effect and duration, weather, target species, locus, mode of application, and the like.
  • the compounds of the invention can also be applied preventively to places at which occurrence of the pests is expected.
  • the compounds of formula I may be also used to protect growing plants from attack or infestation by pests by contacting the plant with a pesticidally effective amount of compounds of formula I.
  • "contacting” includes both direct contact (applying the compounds/compositions directly on the pest and/or plant - typically to the foliage, stem or roots of the plant) and indirect contact (applying the compounds/compositions to the locus of the pest and/or plant).
  • the quantity of active ingredient ranges from 0.0001 to 500 g per 100 m 2 , preferably from 0.001 to 2O g per 100 m 2 .
  • Customary application rates in the protection of materials are, for example, from 0.01 g to 1000 g of active compound per m 2 treated material, desirably from 0.1 g to 50 g per m 2 .
  • lnsecticidal compositions for use in the impregnation of materials typically contain from 0.001 to 95 weight %, preferably from 0.1 to 45 weight %, and more preferably from 1 to 25 weight % of at least one repellent and / or insecticide.
  • the typical content of active ingredient is from 0.001 weight % to 15 weight %, desirably from 0.001 weight % to 5% weight % of active compound.
  • the content of active ingredient is from 0.001 to 80 weights %, preferably from 0.01 to 50 weight % and most preferably from 0.01 to 15 weight %.
  • the rate of application of the active ingredients of this invention may be in the range of 0.1 g to 4000 g per hectare, desirably from 25 g to 600 g per hectare, more desirably from 50 g to 500 g per hectare.
  • the application rates of the mixture are generally from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, in particular from 1 g to 200 g per 100 kg of seed.
  • HPLC column RP-18 column (Chromolith Speed ROD from Merck KgaA, Germany).
  • Furan-2-carboxylic acid N'-[3-(2-fluorophenyl)-2-methyl-allyl]-N-methyl-hydrazide To 114 mg (0.4 mmol) of furan-2-carboxylic acid N-methyl-N'-[2-methyl-3-(2- fluorophenyl)-allylidene]-hydrazide and 38 mg (0.64 mmol) of dimethylamine- borane complex in 1 ml of dichloromethane which were cooled to O 0 C 456 mg (2.4 mmol) of p-toluenesulfonic acid monohydrate in 2ml of dichloromethand/methanol 3:1were added.
  • the heteroatom of the moiety Q is attached to the radical A
  • the active compounds were formulated in 50:50 acetone:water and 100 ppm Kinetic ® surfactant.
  • Cotton plants at the cotyledon stage were infested by placing a heavily infested leaf from the main colony on top of each cotyledon. The aphids were allowed to transfer to the host plant overnight, and the leaf used to transfer the aphids was removed. The cotyledons were dipped in the test solution and allowed to dry. After 5 days, mortality counts were made.
  • the active compounds were formulated in 50:50 acetone:water and 100 ppm Kinetic ® surfactant.
  • Pepper plants in the 2 nd leaf-pair stage (variety 'California Wonder') were infested with approximately 40 laboratory-reared aphids by placing infested leaf sections on top of the test plants. The leaf sections were removed after 24 hr. The leaves of the intact plants were dipped into gradient solutions of the test compound and allowed to dry. Test plants were maintained under fluorescent light (24 hour photoperiod) at about 25 0 C and 20-40% relative humidity. Aphid mortality on the treated plants, relative to mortality on check plants, was determined after 5 days.
  • Dichromothrips corbetti adults used for bioassay were obtained from a colony maintained continuously under laboratory conditions.
  • the test compound was diluted to a concentration of 500 ppm (wt compound: vol diluent) in a 1 :1 mixture of acetone:water, plus 0.01 % Kinetic ® surfactant.
  • Thrips potency of each compound was evaluated by using a floral-immersion technique.
  • Plastic petri dishes were used as test arenas. All petals of individual, intact orchid flowers were dipped into treatment solution for approximately 3 seconds and allowed to dry for 2 hours. Treated flowers were placed into individual petri dishes along with 10 - 15 adult thrips. The petri dishes were then covered with lids. All test arenas were held under continuous light and a temperature of about 28 0 C for duration of the assay. After 4 days, the numbers of live thrips were counted on each flower, and along inner walls of each petri dish.
  • the level of thrips mortality was extrapolated from pre-treatment thrips numbers.
  • Nasturtium plants grown in Metro mix in the 1 st leaf-pair stage were infested with approximately 2-30 laboratory-reared aphids by placing infested cut plants on top of the test plants. The cut plants were removed after 24 hr. Each plant was dipped into the test solution to provide complete coverage of the foliage, stem, protruding seed surface and surrounding cube surface and allowed to dry in the fume hood. The treated plants were kept at about 25°C with continuous fluorescent light. Aphid mortality is determined after 3 days.

Abstract

La présente invention concerne de nouveaux composés d'hydrazide pouvant être employés dans la lutte contre des parasites animaux, notamment des insectes, des arachnides et des nématodes, ainsi que les sels desdits composés. La présente invention concerne également une méthode de lutte contre les insectes, les nématodes et les arachnides. Les composés d'hydrazide selon l'invention sont décrits par la formule générale (I) où ….. représente un vide ou une liaison covalente; A est un radical cyclique éventuellement substitué sélectionné parmi les phényles, les naphtyles et un radical hétérocyclique à 5 ou 6 chaînons comprenant entre 1 et 4 hétéroatomes sélectionnés parmi O, N et S, ces hétéroatomes pouvant être différents les uns des autres, ledit radical hétérocyclique pouvant comprendre un groupement carbonyle comme chaînon cyclique; Q représente une liaison simple, un alkylidène en C1-C4, un alkylidène en O-C1-C4, un alkylidène en S-C1-C4 ou un alkylidène en NR9-C1-C4, ledit groupement alkylidène au sein des quatre radicaux précédents pouvant comporter entre 0 et 4 substituants sélectionnés parmi OH, =O, les halogènes, les halogénoalkyles en C1-C4 et les alcoxy en C1-C4; A-Q peuvent représenter conjointement un groupement alkyle en C1-C10, éventuellement substitué par 1 ou 2 substituants sélectionnés au sein du groupe constitué par =O, OH, les alcoxy en C1-C4, les alkylthio en C1-C4, les halogènes et les alkylcarbonyloxy en C1-C4, X représente C=O, C=S ou SO2; Ar est un radical aromatique éventuellement substitué sélectionné parmi les phényles, les naphtyles, les pyridyles, les pyrimidyles, les furyles et les thiényles; et R1 à R6 et R9 sont tels que décrits dans les revendications et la description.
PCT/EP2005/012787 2004-12-01 2005-11-30 Composes d'hydrazide pour lutter contre des parasites animaux WO2006058730A1 (fr)

Priority Applications (8)

Application Number Priority Date Filing Date Title
AU2005311429A AU2005311429A1 (en) 2004-12-01 2005-11-30 Hydrazide compounds for combating animal pests
US11/791,919 US20070265231A1 (en) 2005-11-30 2005-11-30 Hydrazide Compounds for Combating Animal Pests
MX2007006538A MX2007006538A (es) 2004-12-01 2005-11-30 Compuestos de hidrazida para combatir plagas animales.
JP2007543768A JP2008521856A (ja) 2004-12-01 2005-11-30 有害動物を防除するためのヒドラジド化合物
AP2007004018A AP2007004018A0 (en) 2004-12-01 2005-11-30 Hydrazide compounds for combating animal pests
BRPI0518725-7A BRPI0518725A2 (pt) 2004-12-01 2005-11-30 mÉtodos para o combate de pestes, para a proteÇço de safras contra o ataque ou infestaÇço por pestes e para a proteÇço de materiais nço-vivos contra o ataque ou a infestaÇço por pestes, composto hidrazida, e, composiÇço para o combate de pestes
EP05810640A EP1819224A1 (fr) 2004-12-01 2005-11-30 Composes d'hydrazide pour lutter contre des parasites animaux
IL183198A IL183198A0 (en) 2004-12-01 2007-05-15 Hydrazide compounds for combating animal pests

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US63227404P 2004-12-01 2004-12-01
US60/632,274 2004-12-01

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JP (1) JP2008521856A (fr)
KR (1) KR20070090898A (fr)
CN (1) CN101068468A (fr)
AP (1) AP2007004018A0 (fr)
AU (1) AU2005311429A1 (fr)
BR (1) BRPI0518725A2 (fr)
CR (1) CR9137A (fr)
IL (1) IL183198A0 (fr)
MA (1) MA29112B1 (fr)
MX (1) MX2007006538A (fr)
WO (1) WO2006058730A1 (fr)
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WO2012051708A1 (fr) * 2010-10-21 2012-04-26 The University Of British Columbia Composés antibactériens modulateurs de la pyruvate kinase, compositions, utilisations et méthodes associées
CN103304441A (zh) * 2013-06-09 2013-09-18 南京师范大学 一种邻甲氧基苯乙酸类席夫碱及其合成方法及应用

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CN105837517B (zh) * 2016-04-07 2019-08-06 浙江工业大学 一种含羟基嘧啶的酰肼衍生物及其制备方法与应用

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WO2009059607A2 (fr) 2007-11-05 2009-05-14 Vestergaard Frandsen Sa Pièce comportant deux objets insecticides qui permettent de lutter contre les insectes résistants
WO2012051708A1 (fr) * 2010-10-21 2012-04-26 The University Of British Columbia Composés antibactériens modulateurs de la pyruvate kinase, compositions, utilisations et méthodes associées
CN103304441A (zh) * 2013-06-09 2013-09-18 南京师范大学 一种邻甲氧基苯乙酸类席夫碱及其合成方法及应用
CN103304441B (zh) * 2013-06-09 2016-05-04 南京师范大学 一种邻甲氧基苯乙酸类席夫碱及其合成方法及应用

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JP2008521856A (ja) 2008-06-26
AP2007004018A0 (en) 2007-06-30
CN101068468A (zh) 2007-11-07
BRPI0518725A2 (pt) 2008-12-02
MA29112B1 (fr) 2007-12-03
MX2007006538A (es) 2007-09-11
IL183198A0 (en) 2007-08-19
CR9137A (es) 2008-01-21
EP1819224A1 (fr) 2007-08-22
KR20070090898A (ko) 2007-09-06
AU2005311429A1 (en) 2006-06-08

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