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WO1997008132A1 - Amides d'acide de fluorobutene - Google Patents

Amides d'acide de fluorobutene Download PDF

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Publication number
WO1997008132A1
WO1997008132A1 PCT/EP1996/003570 EP9603570W WO9708132A1 WO 1997008132 A1 WO1997008132 A1 WO 1997008132A1 EP 9603570 W EP9603570 W EP 9603570W WO 9708132 A1 WO9708132 A1 WO 9708132A1
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WO
WIPO (PCT)
Prior art keywords
spp
alkyl
formula
halogen
optionally substituted
Prior art date
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PCT/EP1996/003570
Other languages
German (de)
English (en)
Inventor
Udo Kraatz
Wolfram Andersch
Ulrike Wachendorff-Neumann
Andreas Turberg
Norbert Mencke
Gopichand Yalamanchili
Original Assignee
Bayer Aktiengesellschaft
Monsanto Company
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer Aktiengesellschaft, Monsanto Company filed Critical Bayer Aktiengesellschaft
Priority to CA002230100A priority Critical patent/CA2230100A1/fr
Priority to JP9509775A priority patent/JPH11511438A/ja
Priority to AU68729/96A priority patent/AU6872996A/en
Priority to BR9610023A priority patent/BR9610023A/pt
Priority to EP96929247A priority patent/EP0848698A1/fr
Publication of WO1997008132A1 publication Critical patent/WO1997008132A1/fr
Priority to MXPA/A/1998/001493A priority patent/MXPA98001493A/xx

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C233/09—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an acyclic unsaturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/40—Acylated substituent nitrogen atom
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
    • A01N37/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides containing at least one oxygen or sulfur atom being directly attached to the same aromatic ring system
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
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    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/10—Sulfones; Sulfoxides
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
    • C07C233/15—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/24—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
    • C07C233/27—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/30—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms
    • C07C233/33—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • C07C233/42—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
    • C07C233/44—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a carbon atom of an unsaturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/53—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
    • C07C233/55—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a carbon atom of an unsaturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
    • C07C255/60—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton at least one of the singly-bound nitrogen atoms being acylated
    • C—CHEMISTRY; METALLURGY
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    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C317/34—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring
    • C07C317/38—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring with the nitrogen atom of at least one amino group being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfones
    • C07C317/40—Y being a hydrogen or a carbon atom
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    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
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    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
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    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
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    • 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
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    • C07D333/46—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings substituted on the ring sulfur atom
    • C07D333/48—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings substituted on the ring sulfur atom by oxygen atoms
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    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Definitions

  • the present invention relates to new fluorobutenic acid amides, ner processes for their preparation and their use for controlling animal pests, in particular insects, arachnids and ⁇ ematodes, which occur in agriculture, in forests, in the protection of stocks and materials and in the hygiene sector.
  • R 1 represents hydrogen or halogen
  • R 2 represents hydrogen, alkyl or phenyl which is optionally substituted by halogen or alkyl
  • X represents amino, hydroxy, mercapto, nitro, cyano, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfonyl, haloalkylsulfonyl, alkylcarbonyl, alkoxycarbonyl, alkylamino, dialkylamino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl or haloalkenylcarbonylamyl
  • Y and Z independently of one another represent hydrogen, amino, hydroxy, mercapto, cyano, carboxyl, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylcarbonyl, alkoxycarbonyl, alkylamino, dialkylamino, alkylamino carbonyl or dialkylaminocarbonyl or
  • R 4 represents hydrogen or alkyl
  • n 0, 1, 2, 3 or 4 or
  • a methylene group is replaced by SO 2 or one or two not directly adjacent methylene groups in the ring are replaced by oxygen, sulfur or nitrogen (which is optionally substituted by alkyl, phenyl or benzyl),
  • n 0, 1, 2, 3, 4 or 5 and
  • W represents halogen, alkyl or phenyl which is optionally substituted by halogen, alkyl, haloalkyl, alkoxy or haloalkoxy or
  • 5- or 6-membered hetarylalkyl optionally substituted by halogen, alkyl or by phenyl optionally substituted by halogen, alkyl, haloalkyl, alkoxy or haloalkoxy is one to three heteroatoms from the series consisting of oxygen, sulfur and nitrogen or
  • the compounds of the formula (I) can be present as geometric and / or optical isomers or isomer mixtures of different compositions.
  • the invention relates to both the pure
  • R 1 has the meaning given above
  • Nematodes that are used in agriculture, in forests, in supply and material protection and in the hygiene sector are suitable.
  • Formula (I) provides a general definition of the fluorobutenamides according to the invention.
  • R 1 preferably represents hydrogen, fluorine, chlorine or bromine.
  • R preferably represents hydrogen, C 1 -C 6 alkyl or phenyl optionally substituted by fluorine, chlorine, bromine or C 1 -C 4 alkyl.
  • R 3 preferably represents one of the radicals mentioned under a), b), c), d) or e).
  • Y and Z independently of one another for hydrogen, amino, hydroxy, mercapto,
  • Cyano carboxyl, fluorine, chlorine, bromine, C r C 6 alkyl, C r C 4 haloalkyl, C j -C 6 alkoxy, C 1 -C 4 haloalkoxy, C j -C 8 alkylthio, C ] -C 4 -Halogenal- kylthio, C j -Cg alkylcarbonyl, C j -C 8 - alkoxycarbonyl, C j -Cg alkylamino, di - ⁇ - Cg-alky ⁇ amino, Ci-Cg-alkylaminocarbonyl or Di ⁇ C j -Cg-alkyl) - aminocarbonyl.
  • R 4 represents hydrogen or C r C 4 alkyl
  • n stands for 0, 1 or 2. wherein is optionally replaced by a methyl group SO 2 or (optionally substituted by which C j -C 4 alkyl, phenyl or benzyl) one or two not directly adjacent methylene groups by oxygen, sulfur or nitrogen are replaced,
  • n 0, 1, 2, 3, 4 or 5 and
  • W represents fluorine, chlorine, C j -C 8 alkyl or optionally substituted by fluorine, chlorine, bromine, C r C 4 alkyl, C r C 4 haloalkyl, C r C 4 alkoxy or C r C 4 -Halo- genalkoxy substituted phenyl.
  • Haloalkyl substituted pyridyl or benzthiazolyl is a group consisting of benzthiazolyl.
  • R 1 particularly preferably represents hydrogen or fluorine.
  • R 2 particularly preferably represents hydrogen or C j -C 4 - alkyl.
  • R 3 particularly preferably represents one of the radicals mentioned under a), b), c), d) or e).
  • Y and Z independently of one another for hydrogen, fluorine, chlorine, carboxyl,
  • X 1 represents fluorine, chlorine or C r C 4 alkyl
  • R 4 represents hydrogen, methyl or ethyl.
  • n 0, 2 or 3.
  • R 1 very particularly preferably represents fluorine.
  • R very particularly preferably represents hydrogen or methyl.
  • R 3 very particularly preferably represents one of the radicals mentioned under a), b), c), d) or e).
  • X for nitro, cyano, fluorine, chlorine, bromine, methoxy, trifiuormethoxy, methylthio, methylsulfonyl, ethyl sulfonyl, trifluoromethylsulfonyl, methylcarbonyl, aminocarbonyl or 3,4,4-trifluorobut-3-en-l-yl- carbonylamino stands,
  • Y and Z are independently hydrogen, fluorine, chlorine, carboxyl, methyl, ethyl, n-propyl, isopropyl or trifluoromethyl.
  • X 1 represents chlorine
  • R 4 represents hydrogen or methyl.
  • a particularly emphasized group of compounds are those compounds of formula (I) in which R 3 represents one of the radicals listed under a).
  • R 3 represents one of the radicals listed under c).
  • hydrocarbon radicals such as alkyl or alkenyl
  • heteroatoms such as
  • Alkoxy or alkylthio - as far as possible, straight-chain or branched.
  • the process according to the invention is preferably carried out in the presence of a diluent.
  • Suitable diluents are, in particular, organic solvents, for example optionally chlorinated aliphatic or aromatic hydrocarbons such as cyclohexane, toluene, xylene, dichloromethane, dichloroethane, chloroform or chlorobenzene, ethers such as diethyl ether, dioxane or tetrahydrofuran or
  • Nitriles such as acetonitrile.
  • Two-phase systems consisting of water and an organic solvent, for example water / methylene chloride or water / toluene, are also suitable as diluents.
  • An excess of the amine of formula (II) used is also suitable as a diluent.
  • Amines are preferably used, especially tertiary amines such as triethylamine, diazabicycloundecene (DBU), diazabicyclonones (DBN), diazabicycloctane (DABCO) or pyridine or alkali metal or alkaline earth metal carbonates, hydrogen carbonates or oxides.
  • tertiary amines such as triethylamine, diazabicycloundecene (DBU), diazabicyclonones (DBN), diazabicycloctane (DABCO) or pyridine or alkali metal or alkaline earth metal carbonates, hydrogen carbonates or oxides.
  • DBU diazabicycloundecene
  • DBN diazabicyclonones
  • DABCO diazabicycloctane
  • pyridine alkali metal or alkaline earth metal carbonates
  • hydrogen carbonates or oxides hydrogen carbonates or oxides.
  • the reaction temperature can be varied within a wide range. In general, temperatures between -20 ° C and 140 ° C, preferably between 0 ° C and 60 ° C.
  • the molar ratio of the compound of formula (II) to the compound of formula (III) is generally 2: 1 to 1: 2.
  • the reaction is generally carried out in the pressure range from 0.5 to 6 bar, but preferably under normal pressure.
  • the reaction mixture is hydrolyzed, the product is extracted with an organic solvent such as ethyl acetate, dichloromethane or toluene and the organic phase is then concentrated.
  • an organic solvent such as ethyl acetate, dichloromethane or toluene
  • the amines of the formula (II) required as starting materials are known and / or can be prepared in a simple manner by known methods.
  • the compounds of the formula (I) can also be prepared by amines of the formula (II) with carboxylic acids of the formula (IV)
  • R 1 has the meaning given above
  • the active substances are suitable for controlling animal pests, in particular insects, arachnids and nematodes, which occur in agriculture, in forests, in the protection of stored goods and materials and in the hygiene sector. They can preferably be used as pesticides. They are effective against normally sensitive and resistant species and against all or individual stages of development.
  • the pests mentioned above include:
  • Thysanura e.g. Lepisma saccharina.
  • Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci.
  • Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus sppe, Phros
  • Empoasca spp. Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.
  • Leptinotarsa decemlineata Phaedon cochleariae, Diabrotica spp .. Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatordoderidisilimushimpphppm, spp. , Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp.,
  • Niptus hololeucus Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica.
  • Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
  • Drosophila melanogaster Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tabanus spp.
  • Tannia spp. Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa.
  • Siphonaptera e.g. Xenopsylla cheopis, Ceratophyllus spp., Ctenocephalides felis.
  • Acarina e.g. Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp.,
  • Rhipicephalus spp. Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp ..
  • Plant-parasitic nematodes include e.g. Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp.,
  • Globodera spp. Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp ..
  • the compounds of the formula (I) according to the invention are distinguished in particular by an excellent nematicidal action, for example against Meloidogyne incognita, and by a very good acaricidal action, for example against the common spider mite (Tetranychus urticae).
  • the active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances as well as very fine encapsulation in polymeric substances.
  • formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foaming agents.
  • organic solvents can also be used as auxiliary solvents.
  • auxiliary solvents e.g. aromatics, such as xylene, toluene, or
  • Alkylnaphthalenes chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • chlorobenzenes chlorethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone,
  • ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates, as solid carriers for granules are possible: eg broken and fractionated natural rocks such as caicit, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; suitable emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ether, Al- kyl sulfonates, alkyl sulfates,
  • Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate and natural ones, can be used in the formulations
  • Phospholipids such as cephalins and lecithins and synthetic phospholipids.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes, such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper,
  • Cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.
  • the active substance according to the invention can be used in its commercially available formulations and in the use forms prepared from these formulations
  • Insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms, etc.
  • Bromuconazole Bupirimate, Buthiobate, Calcium polysulfide, captafol, captan, carbendazim, carboxin, quinomethionate (quinomethionate), chloroneb, chloropicrin, chlorothalonil, chlozolinate, cufraneb, cymoxanil, cyproconazole, cyprofuram,
  • Tebuconazole Tebuconazole, tecloftalam, tecnazen, tetraconazole, thiabendazole, thicyofen, thiophanate-methyl, thiram, tolclophos-methyl, tolylfluanid, triadimefon, triadimenol, triazoxide, trichlamid, tricyclazole, tridemorph, trifloriconol, trifloriconol, trifloriconol, trifloriconol
  • Cadusafos Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, CGA 157
  • Fenamiphos fenazaquin, fenbutatin oxide, fenitrothion, fenobucarb, fenothiocarb,
  • Fenoxycarb Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenprox, Fluvalinate, Fonophos, Formothion, Fosthiazat, Fubfenprox, Furathiocarb,
  • Imidacloprid Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivermectin, Lambda-cyhalothrin, Lufenuron, Malathion, Mecarbam, Mervinphos, Mesulfenphos, Metaldehyde, Methacrifos,
  • Methami dophos methidathione, methiocarb, methomyl, metolcarb, milbemectin,
  • Promecarb Propaphos, Propoxur, Prothiofos, Prothoat, Pymetrozin, Pyrachlophos,
  • the active compounds according to the invention can also be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with synergists.
  • Synergists are compounds through which the action of the active ingredients is increased without the added synergist itself having to be active.
  • the active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges.
  • the active substance concentration of the use forms can be from 0.0000001 to 95% by weight of active substance, preferably between 0.0001 and 1% by weight.
  • the application takes place in a customary manner adapted to the application forms.
  • the active ingredient When used against hygiene and storage pests, the active ingredient is characterized by an excellent residual effect on wood and clay as well as a good stability to alkali on limed substrates.
  • the active compounds according to the invention act not only against plant, hygiene and stored-product pests, but also in the veterinary sector against animal parasites (ectoparasites) such as tick ticks, leather ticks, mites, running mites, flies (stinging and licking), parasitic fly larvae, lice,
  • animal parasites ectoparasites
  • tick ticks leather ticks
  • mites running mites
  • flies stinging and licking
  • parasitic fly larvae lice
  • Anoplurida for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp ..
  • Mallophagida and the subordinates Amblycerina and Ischnocerina for example Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp ..
  • Nematocerina and Brachycerina e.g. Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota ., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Glossina spp., Calliphora spp., Glossina spp.,
  • Siphonaptrida e.g. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp ..
  • Actinedida Prostigmata
  • Acaridida Acaridida
  • Acarapis spp. Cheyletiella spp., Ornitrocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp.
  • Tyrophagus spp. Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes ss spnnpnn., OO Cvoddttt spnnpnnn., .. LL Laaammmiiinnnnnosssiiinnonnptttt..eeesss ss spnnpnnn. For example, they show excellent effectiveness against Boophilus microplus and Lucilia cuprina.
  • the active compounds of the formula (I) according to the invention are also suitable for controlling arthropods which are used in agricultural animals, such as e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffalos, rabbits, chickens, turkeys, ducks,
  • Geese bees, other pets such as Dogs, cats, house birds, aquarium fish and so-called experimental animals such as Infest hamsters, guinea pigs, rats and mice.
  • Infest hamsters guinea pigs, rats and mice.
  • the active compounds according to the invention are used in the veterinary sector in a known manner by enteral administration in the form of, for example, tablets, capsules, drinkers, drenches, granules, pastes, boluses, the feed-through method, suppositories, by parenteral administration, such as Example by injections (intramuscular, subcutaneous, intravenous, intraperitonal, etc.), implants, by nasal application, by dermal application in the form of, for example, diving or bathing (dipping), spraying (spray), pouring on (pour-on and spot-on) ), washing, powdering and with the help of shaped articles containing active ingredients such as necklaces, ear tags, tail tags, limb straps,
  • the active compounds of the formula (I) can be used as formulations (for example powders, emulsions, flowable agents) which contain the active compounds in an amount of 1 to 80% by weight, directly or apply after 100 to 10,000-fold dilution or as a chemical
  • k log p Decimal logarithm of the n-octanol / water distribution coefficient, determined by HPLC analysis on reversed phase with
  • Test nematode Meloidogyne incognita solvent: 4 parts by weight acetone
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • the active ingredient preparation is mixed intimately with soil that is heavily contaminated with the test nematodes.
  • the treated soil is filled into pots, lettuce is sown and the pots are kept at a greenhouse temperature of 25 ° C.
  • the lettuce roots are examined for nematode infestation (root galls) and the effectiveness of the active ingredient is determined in%.
  • the degree of efficiency is 100% if the infestation is completely avoided, it is 0% if the infestation is exactly as high as that of the control plants in untreated but contaminated soil in the same way.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Bean plants Phaseolus vulgaris
  • Tetranychus urticae which are heavily affected by all stages of development of the common spider mite Tetranychus urticae, are immersed in an active ingredient preparation of the desired concentration.
  • the kill is determined in%. 100% means that all spider mites have been killed; 0% means that no spider mites have been killed.
  • Test animals adult Musca domestica, Reichswald strain (OP, SP, carbamate-resistant)
  • a suitable formulation three parts by weight of active ingredient are mixed with seven parts of the solvent / emulsifier mixture mentioned above, and the emulsion concentrate thus obtained is diluted with water to the desired concentration.
  • the effectiveness of the active substance preparation is determined. 100% means that all flies have been killed; 0% means that no flies have been killed.
  • the compound according to Preparation Example 12 showed an effectiveness of 100% at an exemplary concentration of 1000 ppm.
  • Test animals All larval stages of Lucilia cuprina (OP-resistant)
  • Emulsifier 35 parts by weight of nonylphenol polyglycol ether
  • a suitable formulation three parts by weight of active ingredient are mixed with seven parts of the solvent / emulsifier mixture mentioned above, and the emulsion concentrate thus obtained is diluted with water to the desired concentration.
  • 30 to 50 larvae per concentration are placed on horse meat (1 cm 3 ) in glass tubes, onto which 500 ⁇ l of the dilution to be tested are pipetted.
  • the glass tubes are placed in plastic beakers, the bottom of which is covered with sea sand, and stored in an air-conditioned room (26 ° C + 1.5 ° C, 70% relative humidity + 10%). The effects are checked after 24 hours and 48 hours (larvicidal action). After the larvae have emigrated (approx. 72 h), the glass tubes are removed and perforated plastic lids are placed on the beakers. After 1 1/2 times the development time (hatching of the control flies), the hatched flies and the dolls / doll covers are counted.
  • Larvae after 48 h (larvicidal effect), or the inhibition of adult hatching from the pupa or the inhibition of pupa formation.
  • the criterion for the in vitro effect of a substance is the inhibition of flea development or a development standstill before the adult stage. 100% larvicidal activity means that all larvae have died after 48 hours. 100% development-inhibiting effect means that no adult flies have hatched.
  • Test animals adult sucked females
  • the test is carried out in 5-fold determination. 1 ⁇ l of the solutions is injected into the abdomen, the animals are transferred to dishes and stored in an air-conditioned room. The effect is determined by the inhibition of egg laying. 100% means that no tick has laid.
  • Solvent 35 parts by weight of ethylene glycol monomethyl ether emulsifier: 35 parts by weight of nonylphenol polyglycol ether
  • a suitable formulation three parts by weight of active ingredient are mixed with seven parts of the solvent / emulsifier mixture mentioned above, and the emulsion concentrate thus obtained is diluted with water to the desired concentration.
  • the effectiveness of the active ingredient preparation is determined. The effectiveness is expressed in%. 100% means that all cockroaches have been killed; 0% means that no cockroaches have been killed.
  • the compounds according to Preparation Examples 12 and 55 have an effectiveness of 100% in each case at an exemplary active ingredient concentration of 1000 ppm.

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Abstract

La présente invention concerne de nouveaux amides d'acide de fluorobutène de formule (I), dans laquelle R1 représente hydrogène ou halogène; R2 représente hydrogène, alkyle ou phényle éventuellement substitué par halogène ou alkyle; R3 représente un des radicaux désignés par a), b), c), où un groupe méthylène est éventuellement remplacé par SO¿2?, ou un ou deux groupes méthylènes non directement adjacents sont remplacés par oxygène, soufre ou azote (ce dernier étant éventuellement substitué par alkyle, phényle ou benzyle); ou d) hétarylalkyle à 5 ou 6 chaînons, éventuellement substitué par alkyle ou par phényle, ce dernier étant éventuellement substitué par halogène, alkyle, halogénure d'alkyle, alcoxy ou halogénure d'alcoxy, et un à trois hétéroatomes de la série oxygène, soufre et azote; ou e) pyridyle ou benzthiazolyle, chacun étant éventuellement substitué par halogène, alkyle ou halogénure d'alkyle, où X, Y, Z, R?4¿, W, n, 1 et m ont la signification mentionnée dans la description. L'invention concerne également un procédé de production de ces nouveaux composés et leur utilisation pour lutter contre les parasites animaux.
PCT/EP1996/003570 1995-08-25 1996-08-13 Amides d'acide de fluorobutene WO1997008132A1 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
CA002230100A CA2230100A1 (fr) 1995-08-25 1996-08-13 Amides d'acide de fluorobutene
JP9509775A JPH11511438A (ja) 1995-08-25 1996-08-13 フルオロブテン酸アミド
AU68729/96A AU6872996A (en) 1995-08-25 1996-08-13 Fluorobutene acid amides
BR9610023A BR9610023A (pt) 1995-08-25 1996-08-13 Flúor butenamidas
EP96929247A EP0848698A1 (fr) 1995-08-25 1996-08-13 Amides d'acide de fluorobutene
MXPA/A/1998/001493A MXPA98001493A (en) 1995-08-25 1998-02-24 Amidas of fluorbutine acid

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19531300A DE19531300A1 (de) 1995-08-25 1995-08-25 Fluorbutensäureamide
DE19531300.3 1995-08-25

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WO1997008132A1 true WO1997008132A1 (fr) 1997-03-06

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JP (1) JPH11511438A (fr)
KR (1) KR19990044034A (fr)
CN (1) CN1200109A (fr)
AU (1) AU6872996A (fr)
BR (1) BR9610023A (fr)
CA (1) CA2230100A1 (fr)
DE (1) DE19531300A1 (fr)
TR (1) TR199800297T1 (fr)
WO (1) WO1997008132A1 (fr)

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WO2013144179A1 (fr) * 2012-03-28 2013-10-03 Intervet International B.V. Composés hétéroaryles à unité de pontage cyclique
CN106554335B (zh) * 2015-09-30 2017-09-19 山东省联合农药工业有限公司 一种反式结构的含内酯环的杀线虫剂及其制备方法和用途
CN106554334B (zh) * 2015-09-30 2017-09-22 山东省联合农药工业有限公司 一种含内酯环的杀线虫剂及其制备方法和用途
CN108484538B (zh) * 2018-06-08 2020-06-12 山东省联合农药工业有限公司 一种含内酯环的杀线虫剂的合成方法
WO2020144695A1 (fr) * 2019-01-09 2020-07-16 Yeda Research And Development Co. Ltd. Modulateurs de l'activité de pin1 et utilisations correspondantes

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WO1992015555A2 (fr) * 1991-03-01 1992-09-17 Monsanto Company Composes fluoroalcenyles et utilisation de ces composes comme insecticides
EP0661289A1 (fr) * 1993-12-29 1995-07-05 Ciba-Geigy Ag Dérivés de vinylcarboxamides comme insecticides et acaricides

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999062866A1 (fr) * 1998-06-02 1999-12-09 Syngenta Participations Ag Difluoroalkencarboxanilides et compositions pesticides
US6852888B2 (en) 1998-06-02 2005-02-08 Syngenta Crop Protection, Inc. Carboxylic acid derivatives
WO2004052872A1 (fr) * 2002-12-11 2004-06-24 Ishihara Sangyo Kaisha, Ltd. Haloalcenes, procede de production d'haloalcenes et pesticides contenant ces haloalcenes

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CA2230100A1 (fr) 1997-03-06
KR19990044034A (ko) 1999-06-25
MX9801493A (es) 1998-08-30
EP0848698A1 (fr) 1998-06-24
TR199800297T1 (xx) 1998-05-21
BR9610023A (pt) 1999-07-06
AU6872996A (en) 1997-03-19
DE19531300A1 (de) 1997-02-27
CN1200109A (zh) 1998-11-25
JPH11511438A (ja) 1999-10-05

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