WO1998055448A2 - Derives d'acides fluoralcenecarboxyliques, procede de production de ces derives, et agents insecticides contenant ces derives - Google Patents

Derives d'acides fluoralcenecarboxyliques, procede de production de ces derives, et agents insecticides contenant ces derives Download PDF

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WO1998055448A2
WO1998055448A2 PCT/EP1998/003214 EP9803214W WO9855448A2 WO 1998055448 A2 WO1998055448 A2 WO 1998055448A2 EP 9803214 W EP9803214 W EP 9803214W WO 9855448 A2 WO9855448 A2 WO 9855448A2
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formula
alkyl
substituted
hydrogen
halogen
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PCT/EP1998/003214
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German (de)
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WO1998055448A3 (fr
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Peter Maienfisch
Tibor GÖGH
Manfred Böger
Thomas Pitterna
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Novartis Ag
Novartis-Erfindungen Verwaltungsgesellschaft Mbh
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Priority to JP50145099A priority Critical patent/JP2002502405A/ja
Priority to EP98932100A priority patent/EP0986534A2/fr
Priority to CA002291441A priority patent/CA2291441A1/fr
Priority to AU82116/98A priority patent/AU734489B2/en
Priority to BR9809912-4A priority patent/BR9809912A/pt
Publication of WO1998055448A2 publication Critical patent/WO1998055448A2/fr
Publication of WO1998055448A3 publication Critical patent/WO1998055448A3/fr

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    • 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
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/53—Nitrogen atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • A01N37/16—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; 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
    • A01N37/28—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
    • 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
    • A01N37/36—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 singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/62—Oximes having oxygen atoms of oxyimino groups esterified
    • C07C251/64—Oximes having oxygen atoms of oxyimino groups esterified by carboxylic acids
    • C07C251/66—Oximes having oxygen atoms of oxyimino groups esterified by carboxylic acids with the esterifying carboxyl groups bound to hydrogen atoms, to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/72—Hydrazones
    • C07C251/86—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/63—Carboxylic acid nitriles containing cyano groups and nitrogen atoms further bound to other hetero atoms, other than oxygen atoms of nitro or nitroso groups, bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/195—Radicals derived from nitrogen analogues of carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18—Fluorenes; Hydrogenated fluorenes

Definitions

  • the present invention relates to new fluoroalkenecarboxylic acid derivatives, processes for their preparation, insecticidal compositions which comprise the new fluoroalkenecarboxylic acid derivatives as active ingredient, and the use of the new fluoroalkenecarboxylic acid derivatives for controlling harmful insects and acarids.
  • the present invention relates to compounds of the formula
  • R 3 is hydrogen, fluorine or methyl; m 0, 1, 2, 3, 4 or 5; n O or l;
  • X is oxygen or NR
  • R 4 represents hydrogen or CrC 6 alkyl or benzyl, which are optionally substituted, and optionally their possible E / Z isomers, E / Z isomer mixtures and / or tautomers, in each case in free form or in salt form, with the proviso that that a) R 3 is not hydrogen or fluorine and m and n are not both 0 when X is oxygen and R 1 and R 2 are independently hydrogen or unsubstituted or substituted alkyl, alkenyl, cycloalkyl, aryl or heteroaryl; b) R 3 is not hydrogen or fluorine and m and n are not both 0 when R 4 is hydrogen and R ⁇ and R 2 are independently hydrogen or unsubstituted or substituted alkyl, aryl or heteroaryl; c) m is not 0, 1 or 2 and R 4 is not hydrogen, alkyl or haloalkyl if one of the radicals R 1 or R 2 is 4-alkylsulfony
  • Preferred groups of compounds of the formula (I) - taking into account the above-mentioned measures - are those in which
  • Ri and R 2 are independently hydrogen or alkyl, cycloalkyl, alkenyl or
  • Alkynyl which are optionally substituted, mean R 3 represents hydrogen, fluorine or methyl, m 0, 1, 2, 3, 4 or 5; n is 0 or 1, X is oxygen or NR 4 , and R 4 is hydrogen or unsubstituted or substituted CC 6 alkyl or benzyl; wherein Ri is hydrogen or unsubstituted or substituted alkyl, alkenyl, alkynyl or
  • R 2 is hydrogen or unsubstituted or substituted aryl or heteroaryl
  • R 3 is hydrogen, fluorine or methyl
  • m is 0, 1, 2, 3, 4 or 5
  • n is 0 or 1
  • X is oxygen or NR 4
  • R 4 is hydrogen or unsubstituted or substituted dC 6 alkyl or benzyl
  • R 1 and R 2 independently of one another denote H or aryl, which are optionally substituted, or R 3 represents hydrogen, fluorine or methyl, m 0, 1, 2, 3, 4 or 5
  • n is 0 or 1
  • X represents oxygen or NR 4 .
  • R 4 represents hydrogen or unsubstituted or substituted C 1 -C 6 -alkyl or benzyl, the general terms used in the above definitions of the substituents R 1, R 2 , R and R 4 are defined below as follows:
  • Halogen means fluorine, chlorine, bromine or iodine, especially fluorine, chlorine or bromine, especially fluorine or chlorine and especially chlorine.
  • Alkyl means straight-chain or branched alkyl radicals having 1 to 20 carbon atoms, which can be unsubstituted or substituted one or more times.
  • R 1 and R 2 as alkyl groups are preferably straight-chain or branched alkyl radicals having 1 to 8 carbon atoms and particularly preferably alkyl radicals having 1 to 4 carbon atoms.
  • Suitable substituents of R T and R 2 as alkyl groups are hydroxyl, halogen, alkoxy, haloalkoxy, alkoxyalkoxy, alkythio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, alkylsulfonyloxy, alkylcarbonyl, dialkylamino, pyrrolidino, piperidino, morphoiino, alkoxycarbonyl, alkylcarbonyloxy , Aryl, aryloxy, arylthio, arylsulfonyl, arylsulfonyloxy, arylcarbonyl or heteroaryl, where aryl or heteroaryl groups in turn are substituted one or more times by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, nitro, cyano, phenoxy, halophenoxy, phenyl
  • alkyl radicals present as alkyl groups in the substituents of R 1 and R 2 preferably have 1 to 4 carbon atoms. These alkyl radicals are particularly preferably methyl or ethyl radicals.
  • R ⁇ and R 2 as alkyl groups are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, 1-methylbutyl, 2,2-dimethylpropyl , Isopentyl, n-hexyl, 2-methylpentyl, 3-methylpentyl, 1, 3-dimethylbutyl, 2-ethylbutyl, n-heptyl, n-octyl, isooctyl, nonyl, decyl, undecyl, dodecyl, hexadecyl and octadecyl.
  • R *. and R 2 as alkyl groups are hydroxy, halogen, alkoxy, haloalkoxy, alkoxyalkoxy, alkythio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, alkylsulfonyloxy, alkylcarbonyl, dialkylamino, pyrrolidino, piperidino, morphoiino, alkoxycarbonyl, alkylcarbonyloxy, cycloalkyl, phenyl, phenyl, phenoxy, phenyl, phenoxy , Phenylsulfonyloxy, benzoyl and pyridyl can be substituted by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, nitro or cyano.
  • a single or multiple substitution of a radical R- or R 2 means in particular a 1 to 4-fold, preferably a 1 to 2-fold and particularly preferably a 1-fold substitution, with R and R 2 in particular as lower alkyl radicals , such as methyl or ethyl, can be perhalogenated, in particular perfluorinated, when substituted by halogen.
  • the respective substituents can be the same or different.
  • Aryl means phenyl or naphthyl, preferably phenyl.
  • Heteroaryl denotes aromatic radicals with 5 or 6 ring members and 1 or 2 heteroatoms, which are selected from the group consisting of nitrogen, oxygen and sulfur.
  • heteroaryl radicals are pyrrolyl, furyl, thienyl, imidazolyl, pyrrazolyl, oxazolyl, thiazolyl, pyridyl, pyridazinyl, pyrimidinyl and pyrazinyl, the radicals R 1 and R 2 as heteroaryl radicals each being bonded via a carbon atom and optionally a benzene ring being fused to these radicals can.
  • Preferred heteroaryl radicals are pyridyl, pyrimidinyl, quinolyl, furyl and thienyl.
  • Aryl residues and heteroaryl residues can be unsubstituted or one or more times by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfonyloxy, haloalkylsulfonyloxy, haloalkoxysulfonyloxy, nitro, cyano, benzoyl, phenyl, phenoxy, phenylthyl, benzylkinoamino, dialylyloxylamino, dialylyloxylamino, trialyl , Pyrrolidino, piperidino, morphoiino, anilino, cycloalkylalkoxy or halocycloalkylalkoxy, heteroaryl or heteroaryloxy, where benzoyl, phenyl, phenoxy, phenylthio, benzyloxy, anilino,
  • Alkenyl means straight-chain or branched alkenyl radicals having 3 to 20, preferably 3 to 8 carbon atoms and particularly preferably alkenyl radicals having 3 to 5 carbon atoms, which can be unsubstituted or substituted one or more times by halogen.
  • Alkenyl preferably denotes those alkenyl radicals which are bonded via a saturated carbon atom, ie alkenyl radicals with a central or terminal double bond.
  • alkenyl radicals are allyl, methallyl, 2-buten-1-yl, 3-butene-1-yl, 2-penten-1-yl, 3-penten-1-yl, 4-penten-1-yl, 2-methyl -2-buten-1-yl, 2-hexen-1-yl, 3-hexen-1-yl, 4-hexen-1-yl, 5-hexen-1yl, 2-hepten-1-yl, 2-octene -1-yl and 2-decen-1 -yl. Allyl and methallyl are particularly preferred alkenyl radicals.
  • Alkynyl means straight-chain or branched alkynyl radicals having 3 to 20, preferably 3 to 8 carbon atoms and particularly preferably alkynyl radicals having 3 to 5 carbon atoms, which may be unsubstituted or substituted one or more times by halogen.
  • Alkynyl preferably denotes those alkynyl radicals which are bonded via a saturated carbon atom, i.e. H. Alkynyl residues with a middle or terminal triple bond.
  • alkynyl radicals are propargyl, 2-butyn-1-yl, 3-butyn-1-yl, 2-, 3- or 4-pentyn-1-yl, 2-, 3-, 4- or 5-hexyn-1 -yl, 2-, 3-, 4-, 5- or 6 heptin-1-yl and 2-, 3-, 4-, 5-, 6- or 7-octin-1yl.
  • a particularly preferred alkynyl radical is the propargyl radical.
  • Cycloalkyl means cycloalkyl radicals having 3 to 7 carbon atoms, which may be unsubstituted or substituted one or more times by halogen, alkyl or haloalkyl, alkyl and haloalkyl radicals preferably containing 1 to 4 carbon atoms and particularly preferably 1 to 2 carbon atoms.
  • cycloalkyl radicals are cyclopropyl, 2-methylcyclopropyl, cyclobutyl, cyclopentyl, 2-methylcyclopentyl, 3,4-dimethylcyclopentyl, cyclohexyl, 2-methylcylohexyl, 4-methylcyclohexyl, 3,4-dimethylcyclohexyl, 2,4-dimethylcyclohexyl and cycloheptyl.
  • the present invention relates in particular to compounds of the general formula (I) in which, taking into account the above-mentioned measures,
  • C Cao-alkyl which is straight-chain or branched and one to four times by hydroxy, halogen, alkoxy, haloalkoxy, alkoxyalkoxy, alkythio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, alkylsulfonyloxy, alkylcarbonyl, dialkylamino, pyrrolidino, piperidino, morphoino, alkoxycarbonylcycloalkylcarbonyl , Phenyl, Naphthyl, Phenoxy, Naphthoxy, Phenylthio, Naphthylthio, Phenylsulfonyl, Naphthylsulfonyl, Phenylsulfonyloxy, Naphthylsulfonyloxy, Benzoyl, Naphthoyl, Heteroaryl or Heteroary
  • Phenylthio or halophenylthio may be substituted
  • Phenyl or naphthyl which is one to four times by halogen, alkyl, haloalkyl, alkoxy,
  • Ring members and 1 to 2 heteroatoms N, O or S can be substituted, with phenyl,
  • Heteroaryloxy radicals as substituents in turn, one or two times by halogen, alkyl,
  • Halogenphenylthio, Cycloalkylalkoxy or Halogencycloalkylalkoxy can be substituted
  • Benzyloxy, anilino, naphthyl, heteroaryl or heteroaryloxy with 5 to 6 ring members and 1 to 2 heteroatoms N, O or S can be substituted, phenyl, phenoxy,
  • Cycloalkylalkoxy or Halogencycloalkylalkoxy may be substituted
  • R 3 is hydrogen, fluorine or methyl; m 0, 1, 2, 3, 4 or 5; n 0 or 1; and
  • X represents oxygen or NR 4 , where R represents hydrogen, CC-alkyl, which can be substituted one or more times by halogen, C 1 -C 4 -alkoxy or di-C C -alkylamino, or stands for benzyl, one or more times by halogen, CC 4 -Alkyl, halogen-C C -alkyl, dd-alkoxy, nitro or cyano may be substituted.
  • R 1 and R 2 independently of one another are hydrogen, C 1 -C 8 -alkyl, which is straight-chain or branched and mono- or disubstituted by hydroxyl, halogen, CrC 4 - Alkoxy, halogen-dC -alkoxy, CC -alkoxyalkoxy, C 1 -C 4 -alkylthio, halogen-C C 4 -alkylthio, CrC -alkylsulfinyl, C ⁇ -C 4 -alkylsulfonyl, CrC lkylsulfonyloxy, d- C 4 -alkylcarbonyl, Di -Crd-alkyiamino, pyrrolidino, piperidino, morphoiino, dC -alkoxycarbonyl, -C-C 4 -alkylcarbonyioxy,
  • C 3 -C 8 alkynyl which can be straight-chain or branched and can be mono- or disubstituted by halogen;
  • C 3 -C cycloalkyl which can be mono- or disubstituted by halogen, CC-alkyl or halogen-C C 4 - alkyl;
  • Phenyl or naphthyl which is mono- or disubstituted by halogen, CrC 4 -alkyl, halogen-C C-alkyl, CC 4 -alkoxy, halogen-C C 4 -alkoxy, C 3 -C 6 -cycloalkyl-C C 4 - alkoxy, halogen-C C 4 - cycloalkyl -CC -alkoxy, CC 4 -alkylthio, halogen-
  • Ring members and 1 to 2 heteroatoms N, O or S can be substituted, with phenyl,
  • Halogen-C 3 -C 6 -cycloalkyl -CC-C 4 alkoxy may be substituted
  • R 3 is hydrogen, fluorine or methyl, m 0, 1, 2, 3 or 4, n 0 or 1 and
  • X represents oxygen or NR
  • R 4 is hydrogen, dC 4 alkyl, which can be mono- or disubstituted by halogen, CrC 4 alkoxy or di-dC 4 alkylamino, or for
  • Benzyl is the one to two times by halogen, dd-alkyl, halogen-dC 4 -alkyl, dC 4 -
  • Alkoxy, nitro or cyano can be substituted.
  • R 3 is hydrogen; b) m denotes 0, 1, 2, 3 or 4, particularly preferably 1 or 4; c) n denotes 0; d) R 4 represents hydrogen; e) Ri and R 2 have the meaning given above, R 3 represents hydrogen, m is 0, 1, 2, 3 or 4, n represents 0 or 1, and X represents oxygen or NH; f) Ri and R 2 have the meaning given above, R 3 stands for hydrogen, m is 1 or 4, n means 0 and X represents oxygen or NH: g) Ri has the meaning given above, R 3 stands for hydrogen and R 2 is a group
  • Alk is methyl or ethyl and the phenyl ring is optionally substituted.
  • Particularly preferred individual compounds are compounds of the formula (I) in which R 3 is hydrogen and a) Ri is hydrogen, R 2 is hydrogen, X is oxygen, m 1 and n 0; b) Ri methyl, R 2 methyl, X oxygen, m 1 and n 0; c) Ri methyl, R 2 phenyl, X oxygen, m 1 and n 0; d) Ri methyl, R 2 4-trifluoromethylphenyl, X oxygen, m 1 and n 0; e) Ri methyl, R 2 4-nitrophenyl, X oxygen, m 1 and n 0; f) R !
  • the present invention further provides a process for the preparation of a compound of the formula (I), characterized in that a) for the preparation of a compound of the formula (I), in which n is 0 and R 1, R 2 , R 3 , X and m have the meaning given above under formula (I), a compound of the formula
  • R 3 and m have the meaning given under formula (I) and Y 2 is Cl, Br or OSO 2 alkyl, with a compound of the formula
  • the starting materials of the formula (III) can be prepared in a manner known per se by reacting a ketone of the above formula (V) with hydrazine, a hydrazine monosubstituted by R 4 as defined above or with hydroxylamine, the ketones of the formula (V) in turn are accessible by the known processes customary for the production of ketones.
  • the starting materials of formula (II) can be obtained by using an acid halide of the formula
  • the starting materials of formula (VII) can be obtained by using a chloroacetic acid halide, e.g. B. chloroacetyl chloride, with a compound of formula (III) as defined above.
  • Process a) is preferably not carried out in an inert, hydroxyl-free solvent in the presence of an organic base, such as, for example, pyridine, 4-dimethylaminopyridine, 4-pyrrolidinopyridine, lutidine, coilidine, trialkylamine, N, N-dialkylaniline, or a bicyclic one nucleophilic base such as 1,4-diazabicyclo [2.2.2] octane (DABCO),
  • DABCO 1,4-diazabicyclo [2.2.2] octane
  • DBN 1,5-diazabicyclo [4.3.0] non-5-ene
  • DBU 1,8-diazabicyclo [5.4.0] undec-7-ene
  • the reaction is generally carried out at temperatures from -30 ° C. to + 70 ° C., preferably from -10 ° C. to + 50 ° C.
  • the procedure is expediently carried out in the presence of an inert solvent or solvent mixture.
  • Aliphatic and aromatic hydrocarbons such as benzene, toluene, xylenes, petroleum ether, hexane are suitable for this purpose; halogenated hydrocarbons such as chlorobenzene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, tetrachlorethylene; Ethers and ethereal compounds such as dialkyl ether (diethyl ether, diisopropyl ether, tert-butyl methyl ether, etc.) anisole, dioxane, tetrahydrofuran; Nitriles such as acetonitrile, propionitrile; Esters such as ethyl acetate (ethyl acetate), propyl acetate or butyl acetate; Ketones such as acetone, diethyl ketone, methyl ethyl ketone; and mixtures of such solvents with one another.
  • reaction can also be carried out in excess of one of the bases mentioned above, or a second equivalent or a larger excess of the compound of I can also be used instead of the base.
  • the reaction is carried out under the pressure of the environment, although it could also be carried out under increased or reduced pressure.
  • the reaction of process b) is advantageously carried out in an inert solvent at a temperature of 20 ° C. to 150 ° C., preferably at 40 ° C. to 120 ° C., optionally in the presence of a catalytic amount of an acid, such as acetic acid or p-toluenesulfone. acid.
  • Preferred inert solvents are lower alkanols, especially methanol and ethanol.
  • reaction of process c) is advantageously carried out in an inert solvent in the presence of a base and, if appropriate, in the presence of a catalyst, such as NaI or CsF, with polar aprotic solvents such as N, N-dimethylformamide, dimethyl sulfoxide, dioxane being preferred as the inert solvent and tetrahydrofuran.
  • a catalyst such as NaI or CsF
  • polar aprotic solvents such as N, N-dimethylformamide, dimethyl sulfoxide, dioxane being preferred as the inert solvent and tetrahydrofuran.
  • pyridine, 4-dimethylaminopyridine, 4-pyrrolidinopyridine, lutidine, coilidine, trialkylamine, N, N-dialkylaniline, or a bicyclic base are not bases nucleophilic base such as 1,4-diazabicyclo [2.2.2] octane (DABCO), 1,5-diazabicyclo [4.3.O] non-5-ene (DBN) or 1,8-diazabicyclo [5.4.0] undec-7 -en (1, 5-5) (DBU), suitable.
  • DABCO 1,4-diazabicyclo [2.2.2] octane
  • DBN 1,5-diazabicyclo [4.3.O] non-5-ene
  • DBU 1,8-diazabicyclo [5.4.0] undec-7 -en (1, 5-5)
  • reaction described above and below are carried out in a manner known per se, e.g. in the absence or, where appropriate, in the presence of a suitable solvent or diluent or a mixture thereof, with cooling, at room temperature or with heating, e.g. in a temperature range from about -80 ° C to the boiling temperature of the reaction mixture, preferably from about -20 ° C to about + 150 ° C, and, if necessary, in a closed vessel, under pressure, in an inert gas atmosphere and / or under anhydrous Conditions works. Particularly advantageous reaction conditions can be found in the examples.
  • the compounds of the formula (I) according to the invention are valuable active ingredients in the field of pest control, while being well tolerated by warm-blooded animals, fish and plants.
  • the active compounds according to the invention act against insects and arachnids, as they occur on useful and ornamental plants in agriculture and horticulture, in particular in rice, cotton, vegetable and fruit plantations, and in the forest.
  • the compounds of the formula (I) are particularly suitable for controlling insects in rice, fruit and vegetable crops, in particular insects which damage plants, such as Aphis craccivora, Nilaparvata lugens and Nephotettix cincticeps.
  • the compounds of the formula (I) are active against all or individual stages of development of normally sensitive, but also of resistant types of pests. Their effect can be such. B. in a killing of the pests, which occurs immediately or only after some time, for example when molting, or in a reduced egg laying and / or hatching rate.
  • the animal pests mentioned include, for example, those which are mentioned in European patent application EP-A-736'252.
  • EP-A-736'252 is therefore included by reference in the present subject matter.
  • the compounds of the formula (I) are particularly suitable as active compounds for controlling pests from the Homoptera order and from the Akarina order.
  • the compounds of the formula (I) are particularly suitable for controlling the pests in cotton, vegetable, fruit and rice crops, such as spider mites, aphids, and caterpillars and rice cicadas.
  • Spider mites like Panonychus ulmi
  • aphids like Aphis craccivora
  • caterpillars like those of Heliothis virescens and rice leafhoppers like Nilaparvata lugens or Nephotettix cincticeps can be checked.
  • the good pesticidal activity of the compounds of the formula (I) according to the invention corresponds to a mortality rate of at least 50-60% of the pests mentioned.
  • the action of the compounds of the formula (I) according to the invention and the compositions comprising them can be broadened considerably by adding other insecticides and / or acaricides and adapted to the given circumstances.
  • Representatives of the following classes of active substances are suitable as additives: organic phosphorus compounds, nitrophenols and derivatives, formamidines, ureas, carbamates, pyrethroids, chlorinated hydrocarbons and Bacillus thuringiensis preparations.
  • the compounds of the formula (I) are used in unchanged form or, preferably, together with the auxiliaries customary in formulation technology and can therefore, for example, also to emulsifiable concentrates, directly sprayable or dilutable solutions, diluted emulsions, wettable powders, soluble powders, dusts, granules Encapsulations in polymeric substances are processed in a known manner.
  • the application methods such as spraying, atomizing, dusting, scattering or pouring, as well as the agents, are chosen in accordance with the desired goals and the given conditions.
  • the formulation that is to say an active ingredient (I), or combinations of these active ingredients with other insecticides or acaricides, and, if appropriate, agents, preparations or compositions comprising a solid or liquid additive are prepared in a known manner, for example by intimate mixing and / or Grinding the active ingredients with extenders, such as with solvents, solid carriers, and optionally surface-active compounds (surfactants).
  • extenders such as with solvents, solid carriers, and optionally surface-active compounds (surfactants).
  • auxiliaries such as solvents, solid carriers, surface-active compounds, nonionic surfactants, cationic surfactants, anionic surfactants and other auxiliaries in the agents used according to the invention are, for example, the same as those described in EP-A-736'252.
  • the pesticidal preparations generally contain 0.1 to 99%, in particular 0.1 to 95%, of active ingredient I or of the combination of this active ingredient with other insecticides and / or acaricides and 1 to 99.9%, in particular 5 to 99.9%, of a solid or liquid auxiliary, it being possible for the preparations to be, as a rule, 0 to 25%, in particular 0.1 to 20%, surfactants (% means weight percent). While concentrated products are preferred as a commercial product, the end user generally uses diluted preparations which have significantly lower active substance concentrations. Typical application concentrations are between 0.1 and 1000 ppm, preferably between 0.1 and 500 ppm. The application rates per hectare are generally 1 to 1000 g of active ingredient per hectare, preferably 25 to 500 g / ha.
  • Emulsifiable concentrates are:
  • Active ingredient 1 to 90%, preferably 5 to 20%
  • Surfactant 1 to 30%, preferably 10 to 20% liquid carrier: 5 to 94%, preferably 70 to 85%
  • Active ingredient 0.1 to 10%, preferably 0.1 to 1% solid carrier: 99.9 to 90%, preferably 99.9 to 99%
  • Active ingredient 5 to 75%, preferably 10 to 50%
  • Surfactant 1 to 40%, preferably 2 to 30%
  • Active ingredient 0.5 to 90%, preferably 1 to 80%
  • Surfactant 0.5 to 20%, preferably 1 to 15% solid carrier: 5 to 95%, preferably 15 to 90%
  • Active ingredient 0.5 to 30%, preferably 3 to 15% solid carrier 99.5 to 70%, preferably 97 to 85%
  • the preparations can also contain other auxiliaries, such as stabilizers, e.g. B. optionally epoxidized vegetable oils (e.g. epoxidized coconut oil, rapeseed oil or soybean oil), defoamers, z. B. silicone oil, preservatives, viscosity regulators, binders and / or adhesives, as well as fertilizers or other active ingredients to achieve special effects.
  • stabilizers e.g. B. optionally epoxidized vegetable oils (e.g. epoxidized coconut oil, rapeseed oil or soybean oil), defoamers, z. B. silicone oil, preservatives, viscosity regulators, binders and / or adhesives, as well as fertilizers or other active ingredients to achieve special effects.
  • epoxidized vegetable oils e.g. epoxidized coconut oil, rapeseed oil or soybean oil
  • defoamers e.g. epoxidized coconut oil, rape
  • DAHSCI 6,6-difluoro-5-hexenoyl chloride
  • 0.5 g (10 mmol) of the hydrazine hydrate is added to a solution of 0.9 g (10 mmol) of methyl glycolate in 10 ml of methanol.
  • the solution is heated under reflux on the water bath for 10 minutes and then concentrated in a rotary evaporator.
  • the residue is reslurried in 10 ml of methanol, mixed with 0.58 g (10 mmol) of acetone and stirred for a further 10 hours at room temperature. After evaporating off the methanol, the residue is slurried in 20 ml of dichloromethane-tetrahydrofuran.
  • Example B1 Ovicidal action on Heliothis virescens
  • Eggs from Heliothis virescens deposited on filter paper are briefly immersed in an acetonic-aqueous test solution containing 400 ppm of the active ingredient to be tested. After the test solution has dried on, the eggs are incubated in petri dishes. After 6 days, the percentage hatching of the eggs is evaluated in comparison to untreated control batches (% hatching reduction).
  • Example B2 Action against Nilaparvata luoens
  • Rice plants are treated with an aqueous emulsion spray mixture which contains 400 ppm of the active ingredient. After the spray coating has dried on, the rice plants are colonized with 2nd and 3rd stage larvae of Nilaparvata lugens. Evaluation takes place 21 days later. The percentage reduction in population (% action) is determined by comparing the number of surviving cicadas on the treated plants with those on the untreated plants. The compounds of Tables 1-20 show a good activity against Nilaparvata lugens in this test.
  • connections 4.80, 4.53, 4.78, 4.12, 4.21, 4.79, 4.02, 4.36, 4.26, 5.76, 5.77, 5.53, 5.21, 5.78, 5.02, 5.12, 5.79, 5.36, 5.26, 5.80, 6.53, 6.21, 6.78 , 6.79, 6.12, 6.02, 6.36, 6.26 and 6.80 show an effect over 80%.
  • Corn seedlings are sprayed with an aqueous emulsion spray mixture which contains 400 ppm of the active ingredient. After the spray coating has dried on, the maize seedlings are populated with 10 larvae of Diabrotica balteata of the second stage and placed in a plastic container. Evaluation takes place 6 days later. The percentage reduction in the population (% activity) is determined by comparing the number of dead larvae on the treated plants with those on the untreated plants.
  • the compounds of Tables 1-20 show good activity against Diabrotica balteata in this test.
  • the connections 4.80, 4.53, 4.78, 4.12, 4.21, 4.79, 4.02, 4.36, 4.26, 5.76, 5.77, 5.53, 5.21, 5.78, 5.02, 5.12, 5.79, 5.36, 5.26, 6.53, 6.21, 6.78, 6.79 , 6.12, 6.02, 6.26 and 6.80 show an effect over 80%.
  • Example B4 Action against Tetranychus urticae
  • Young bean plants are populated with a mixed population of Tetranychus urticae and sprayed with an aqueous emulsion spray mixture containing 400 ppm of the active ingredient 1 day later. The plants are then incubated at 25 ° C. for 6 days and then evaluated. The percentage reduction in the population (% activity) is determined by comparing the number of dead eggs, larvae and adults on the treated plants with those on the untreated plants.
  • the compounds of Tables 1-20 show a good activity against Tetranychus urticae in this test.
  • the connections 4.80, 4.53, 4.78, 4.12, 4.21, 4.79, 4.02, 4.36, 4.26, 5.76, 5.77, 5.53, 5.21, 5.78, 5.02, 5.12, 5.79, 5.36, 5.26, 5.80, 6.53, 6.21, 6.78 , 6.12, 6.02, 6.36, 6.26 and 6.80 show an effect over 80%.
  • Example B5 Activity against Spodoptera littoralis caterpillars
  • Young soybean plants are sprayed with an aqueous emulsion spray mixture which contains 400 ppm of the active ingredient. After the spray coating has dried on, the soy plants are populated with 10 caterpillars of the third stage of Spodoptera littoralis and placed in a plastic container. The evaluation is carried out three days later. From the comparison the number of dead caterpillars and the feeding damage on the treated to those on the untreated plants is the percentage reduction in the population or. determines the percentage reduction in feeding damage (% effect).
  • the compounds of Tables 1-20 show a good activity against Spodoptera littoralis in this test.
  • the compounds 4.80, 4.53, 4.12, 4.21, 4.36, 5.77, 5.53, 5.21, 5.78, 5.79, 5.36, 5.26, 5.80, 6.53, 6.21, 6.12, 6.02, 6.36, 6.26 and 6.80 show an effect above 80%.
  • Example B6 Action against Plutella xylostella caterpillars
  • Young cabbages are sprayed with an aqueous emulsion spray mixture which contains 400 ppm of the active ingredient. After the spray coating has dried on, the cabbages are populated with 10 caterpillars of the third stage of Plutella xylostella and placed in a plastic container. Evaluation is carried out 3 days later. By comparing the number of dead caterpillars and the damage caused by feeding on the treated plants to those on the untreated plants, the percentage reduction in the population or determines the percentage reduction in feeding damage (% effect).
  • the compounds of Tables 1-20 show good activity against Plutella xylostella in this test.
  • the compounds 4.80, 4.53, 4.78, 4.12, 4.21, 4.79, 4.02, 4.36, 4.26, 5.77, 5.53, 5.78, 5.36, 5.26, 5.80, 6.53, 6.21, 6.78, 6.12, 6.02 and 6.80 in particular show an effect 80%.
  • Example B7 Action against Aphis craccivora
  • Pea seedlings are infected with Aphis craccivora and then sprayed with a spray mixture containing 400 ppm of the active ingredient and incubated at 20 ° C. Evaluation is carried out 3 and 6 days later. The percentage reduction in the population (% action) is determined by comparing the number of dead leaves on the treated plants with those on the untreated plants.
  • the compounds of Tables 1-20 show good activity against Aphis craccivora in this test. Especially the compounds 4.80, 4.53, 4.78, 4.12, 4.21, 4.79, 4.36, 4.26, 5.77, 5.53, 5.21, 5.78, 5.26, 5.80, 6.53, 6.21, 6.78, 6.12, 6.02 and 6.80 show an effect over 80% .
  • Example B8 Action against Mvzus persicae
  • Pea seedlings are infected with Myzus persicae and then sprayed with a spray mixture containing 400 ppm of the active ingredient and incubated at 20 ⁇ C. Evaluation is carried out 3 and 6 days later. The percentage reduction in population (% activity) is determined by comparing the number of dead aphids on the treated plants with those on the untreated plants.
  • Example B9 Systemic action against Mvzus persicae
  • Pea seedlings are infected with Myzus persicae, then placed with the roots in a spray mixture containing 400 ppm of the active ingredient and incubated at 20 % C. Evaluation is carried out 3 and 6 days later. The percentage reduction in population (% activity) is determined by comparing the number of dead aphids on the treated plants with those on the untreated plants.
  • the compounds of Tables 1-20 show a good activity against Myzus persicae in this test.
  • the compounds 4.80, 4.53, 4.78, 4.12, 4.21, 4.79, 4.02, 4.36, 5.21, 5.78, 5.02, 5.12, 6.21, 6.78, 6.79, and 6.80 show an activity above 80%.
  • Example B11 Action against Tetranychus urticae omuld
  • Young bean plants are populated with Tetranychus urticae females, which are removed after 24 hours.
  • the plants populated with eggs are with a sprayed aqueous emulsion broth containing 400 ppm of the active ingredient.
  • the plants are then incubated for 6 days at 25 ° C. and then evaluated.
  • the percentage reduction in the population is determined by comparing the number of dead eggs, larvae and adults on the treated plants with those on the untreated plants.
  • the compounds of Tables 1-20 show a good activity against Tetranychus urticae in this test.
  • the connections 4.53, 4.78, 4.12, 4.21, 4.79, 4.02, 4.36, 4.26, 5.76, 5.77, 5.53, 5.21, 5.78, 5.12, 5.79, 5.36, 5.26, 5.80, 6.53, 6.21, 6.78, 6.12, 6.02 , 6.36, 6.26 and 6.80 show an effect above 80%.
  • Example B12 Action against Panonvchus ulmi (OP and carb. Resistant)
  • Apple seedlings are colonized with adult Panonychus ulmi females. After seven days, the infected plants are sprayed to runoff point with an aqueous emulsion spray liquor containing 400 ppm of the compound to be tested and cultured in a greenhouse. The evaluation is carried out after 14 days. The percentage reduction in population (% activity) is determined by comparing the number of dead spider mites on the treated plants with those on the untreated plants.

Abstract

L'invention concerne des dérivés d'acides fluoroalcènecarboxyliques de formule générale (I) dans laquelle R1 et R2 désignent, indépendamment l'un de l'autre, un hydrogène, ou un alkyle, un groupe de formule (II), ou des groupes aryle, cycloalkyle, alcényle, alcynyle éventuellement substitués; R3 est un hydrogène, un fluor ou un méthyle; m = 0, 1, 2, 3, 4 ou 5; n = 0 ou 1; X est un oxygène ou NR4, et R4 est un hydrogène ou un alkyle en C1-C6, ou un benzyle éventuellement substitués. L'invention concerne en outre leur procédé de fabrication, des agents insecticides renfermant, comme matière active, les nouveaux dérivés d'acides fluoroalcènecarboxyliques, ainsi que leur utilisation pour lutter contre les insectes nuisibles et les acariens.
PCT/EP1998/003214 1997-06-03 1998-05-29 Derives d'acides fluoralcenecarboxyliques, procede de production de ces derives, et agents insecticides contenant ces derives WO1998055448A2 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
JP50145099A JP2002502405A (ja) 1997-06-03 1998-05-29 フルオロアルケンカルボン酸誘導体、その製造方法及びそれを含んで成る殺虫組成物
EP98932100A EP0986534A2 (fr) 1997-06-03 1998-05-29 Composes organiques
CA002291441A CA2291441A1 (fr) 1997-06-03 1998-05-29 Derives d'acides fluoralcenecarboxyliques, procede de production de ces derives, et agents insecticides contenant ces derives
AU82116/98A AU734489B2 (en) 1997-06-03 1998-05-29 Fluoroalkenecarboxylic acid derivatives, processes for their preparation and insecticidal compositions comprising them
BR9809912-4A BR9809912A (pt) 1997-06-03 1998-05-29 "derivados de ácidos fluoralquenocarboxìlicos, processos para sua preparação e composições inseticidas que compreendem tais derivados"

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH1327/97 1997-06-03
CH132797 1997-06-03

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WO1998055448A3 WO1998055448A3 (fr) 1999-05-06

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JP (1) JP2002502405A (fr)
CN (1) CN1259118A (fr)
AU (1) AU734489B2 (fr)
BR (1) BR9809912A (fr)
CA (1) CA2291441A1 (fr)
WO (1) WO1998055448A2 (fr)

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US8241822B2 (en) 2003-02-19 2012-08-14 Basf Se Halogenated oxime derivatives and the use therof as latent acids
US9624220B2 (en) 2010-04-01 2017-04-18 Critical Outcome Technologies Inc. Compounds and method for treatment of HIV
WO2018190321A1 (fr) 2017-04-10 2018-10-18 三井化学アグロ株式会社 Agent d'extermination d'organismes nuisibles parasites ayant un composé pyridone pour principe actif, et procédé de mise en œuvre de celui-ci

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US7842727B2 (en) 2001-03-27 2010-11-30 Errant Gene Therapeutics, Llc Histone deacetylase inhibitors
AU2003243272A1 (en) 2002-05-22 2003-12-12 Errant Gene Therapeutics, Llc Histone deacetylase inhibitors based on alpha-ketoepoxide compounds
WO2003099789A1 (fr) 2002-05-22 2003-12-04 Errant Gene Therapeutics, Llc. Inhibiteurs d'histone desacetylase bases sur des composes alpha-chalcogenmethylcarbonyle
CA2710039C (fr) 2007-12-26 2018-07-03 Critical Outcome Technologies, Inc. Semicarbazones, thiosemicarnazones et composes associes, et methodes de traitement du cancer
WO2010006438A1 (fr) 2008-07-17 2010-01-21 Critical Outcome Technologies Inc. Composés inhibiteurs et procédés de traitement du cancer

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EP0662472A1 (fr) * 1994-01-05 1995-07-12 Ciba-Geigy Ag Dérivés d'hydrazone comme pesticides
DE19524436A1 (de) * 1995-07-05 1997-01-09 Bayer Ag Fluorbutensäureoximester
WO1998003475A1 (fr) * 1996-07-24 1998-01-29 Novartis Ag Compositions pesticides
WO1998006710A1 (fr) * 1996-08-08 1998-02-19 Novartis Ag Derives substitues de la 4-nitro-imino-perhydro-1,3,5-oxadiazine, leur utilisation comme pesticides, et intermediaires pour leur preparation

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Publication number Priority date Publication date Assignee Title
EP0662472A1 (fr) * 1994-01-05 1995-07-12 Ciba-Geigy Ag Dérivés d'hydrazone comme pesticides
DE19524436A1 (de) * 1995-07-05 1997-01-09 Bayer Ag Fluorbutensäureoximester
WO1998003475A1 (fr) * 1996-07-24 1998-01-29 Novartis Ag Compositions pesticides
WO1998006710A1 (fr) * 1996-08-08 1998-02-19 Novartis Ag Derives substitues de la 4-nitro-imino-perhydro-1,3,5-oxadiazine, leur utilisation comme pesticides, et intermediaires pour leur preparation

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8241822B2 (en) 2003-02-19 2012-08-14 Basf Se Halogenated oxime derivatives and the use therof as latent acids
US9624220B2 (en) 2010-04-01 2017-04-18 Critical Outcome Technologies Inc. Compounds and method for treatment of HIV
WO2018190321A1 (fr) 2017-04-10 2018-10-18 三井化学アグロ株式会社 Agent d'extermination d'organismes nuisibles parasites ayant un composé pyridone pour principe actif, et procédé de mise en œuvre de celui-ci

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AU8211698A (en) 1998-12-21
AU734489B2 (en) 2001-06-14
EP0986534A2 (fr) 2000-03-22
CA2291441A1 (fr) 1998-12-10
JP2002502405A (ja) 2002-01-22
BR9809912A (pt) 2000-10-03
WO1998055448A3 (fr) 1999-05-06

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