WO2006118267A1 - Composé de type anthranylamide, méthode de synthèse dudit composé et agent pesticide contenant ledit composé - Google Patents

Composé de type anthranylamide, méthode de synthèse dudit composé et agent pesticide contenant ledit composé Download PDF

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Publication number
WO2006118267A1
WO2006118267A1 PCT/JP2006/309025 JP2006309025W WO2006118267A1 WO 2006118267 A1 WO2006118267 A1 WO 2006118267A1 JP 2006309025 W JP2006309025 W JP 2006309025W WO 2006118267 A1 WO2006118267 A1 WO 2006118267A1
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alkyl
compound
halogen
haloalkyl
reaction
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PCT/JP2006/309025
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English (en)
Japanese (ja)
Inventor
Toru Koyanagi
Masayuki Morita
Toshihiko Ueki
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Ishihara Sangyo Kaisha, Ltd.
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Publication of WO2006118267A1 publication Critical patent/WO2006118267A1/fr

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/40—2,5-Pyrrolidine-diones
    • C07D207/416—2,5-Pyrrolidine-diones 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 other ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

  • Patent Documents 1 and 2 each disclose an anthramide compound having a certain chemical structure. However, it has an alkyl substituted with C cycloalkyl as a substituent corresponding to A in the following formula (I).
  • Patent Document 3 discloses a compound in which the acyl group bonded to the amino moiety of the anthranylamide is a pyrazole carbonyl group, and the nitrogen substituent of the amide moiety is cyclopropylmethyl.
  • the substituent bonded to anthralamide is pyrrole, and the chemical structures of the two are different.
  • Patent Document 1 International Publication WO03Z24222
  • Patent Document 2 International Publication WO01Z70671
  • Patent Document 3 International Publication WO04Z67528
  • a number of pest control agents have been used for many years, but many have various problems such as insufficient efficacy, pests gaining resistance and limiting their use. Therefore, it is desired to develop a new pest control agent with few disadvantages, for example, a pest control agent capable of controlling various pests that are problematic in the field of agriculture and horticulture, and pests parasitic on animals.
  • the present inventors have made various studies on anthranilamide compounds in order to find better pest control agents. As a result, the present inventors have found that a novel anthra-amide compound has an extremely high control effect against pests at a low dose, and completed the present invention.
  • R 1 is halogen or alkyl
  • R 2 is a hydrogen atom, halogen, alkyl, haloalkyl, cyano or methoxycarbon
  • each of R 3 , R 4 and R 5 is Halogen; alkyl; haloalkyl; alkoxy; haloalkoxy; formyl; alkoxyalkyloxymethyl; cycloalkylcarbonyl; haloalkylcarbonyl; substituted with alkoxy, alkylamino or dialkylamino, or iminoalkyl; or An alkyl substituted with 1 or 2 cyanos;
  • R 6 is a halogen, alkyl or haloalkyl;
  • A is a hydrogen atom; alkyl; alkylthioalkyl; haloalkylthioalkyl; alkylsulfinylalkyl; haloalkylsulfinylalkyl; Sulfonylalkyl
  • Element A halogen, alkyl or haloalkyl, provided that (1) when A is a hydrogen atom, alkyl, alkylthioalkyl, alkylsulfinylalkyl or alkylsulfonylalkyl, any of R 3 , R 4 or R 5 1 One is formyl; alkoxyalkyloxymethyl; cycloalkylcarbonyl; haloalkylcarbonyl; iminoalkyl optionally substituted with alkoxy, alkylamino or dialkylamino; or an alkyl substituted with 1 or 2 cyanos; ) When R 3 and R 5 are hydrogen atoms and R 4 is halogen, haloalkyl or haloalkoxy, A is not haloalkylthioalkyl, haloalkylsulfuralkyl or haloalkylsulfoalkyl.
  • a pest control agent comprising the novel anthranilamido compound of formula (I) as an active ingredient is
  • Examples of the halogen in R 6 , R 7 or A or the halogen as a substituent include each atom of fluorine, chlorine, bromine or iodine.
  • the number of halogens as substituents is 1 or 2 or more. When 2 or more, each halogen may be the same or different. Further, the halogen substitution position may be any position.
  • Alkyl or alkyl moieties in R 6 , R 7 or A include linear or branched C alkyl such as methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, hexyl. Can be mentioned.
  • Examples of the cycloalkyl part of the cycloalkyl carbonyl of R 3 , R 4 or R 5 include C alkyl such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
  • R 3 , IT or R 5 alkalis examples include linear or branched C alkalis such as bur, aryl, 1-probe and iso-probe.
  • the cycloalkyl part of C cycloalkyl-alkyl of A includes cyclopropyl
  • cyclobutyl is mentioned. Of these, cyclopropyl is desirable.
  • Halogen, alkyl or haloalkyl which is a C cycloalkyl-alkyl substituent of A
  • the number of substitutions of alkyl is 1 or 2 or more. When it is 2 or more, each substituent may be the same or different. In addition, the substitution position of each substituent may be a shift position.
  • Chloalkyl-alkyl is preferably unsubstituted or has 1 to 5 substituents if it has the above-mentioned substituents.
  • the salt of the anthracamide compound of the formula (I) includes any salt that is agriculturally acceptable.
  • alkali metal salts such as sodium salt and potassium salt
  • alkaline earth metal salts such as magnesium salt and calcium salt
  • ammonium salt such as dimethyl ammonium salt and triethyl ammonium salt
  • hydrochloride salt Inorganic salts such as perchlorate, sulfate, nitrate
  • organic acid salts such as acetate, methanesulfonate, etc. It is done.
  • the anthranilamide-based compound of the formula (I) may have different isomers such as optical isomers and geometric isomers. In the present invention, both isomers and isomer mixtures are present. Is included.
  • the present invention includes various isomers other than those described above within the scope of common technical knowledge in the technical field. In addition, depending on the type of isomer, there may be a chemical structure different from that of the above formula (I). However, since those skilled in the art can sufficiently recognize that they are related to isomers, Obviously, it is within range.
  • the anthracamide compound of the formula (I), its N-oxide or a salt thereof (hereinafter abbreviated as the present invention compound) is prepared by the following reactions [A] to [B] and production of ordinary salts: It can be manufactured according to the method.
  • the reaction [A] can usually be carried out in the presence of a base when Z is a chlorine atom.
  • the base include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; sodium hydride, water Alkali metal hydrides such as potassium iodide; trimethylamine, triethylamine, triisopropylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, 2,6-dimethylviridine, 4 pyrrolidinopyridine, N-methyl Tertiary amines such as morpholine, ⁇ , ⁇ dimethylaniline, ⁇ , ⁇ jetylaniline, ⁇ ethyl- ⁇ -methylaniline, 1,8 diazabicyclo [5.4.0] 7undecene, 1,4-diazabicyclo [2.2.2] octane
  • One type or two or more types can be appropriately selected from the
  • the reaction [ ⁇ ] can be carried out in the presence of a solvent if desired when ⁇ is a chlorine atom.
  • a solvent may be used as long as it is inert to the reaction.
  • etherols such as diethyl ether, butyl ether, tetrahydrofuran, dioxane, dimethoxyethane; halogenated compounds such as black benzene, dichlorobenzene, dichloromethane, chlorophenol, carbon tetrachloride, dichloroethane, trichloroethane, dichloroethylene Hydrocarbons; aromatic hydrocarbons such as benzene, toluene, xylene; acetonitryl, propio-tolyl, ⁇ , ⁇ ⁇ ⁇ ⁇ dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, dimethylacetamide, ⁇ —Polar aprotic solvents such
  • the reaction [ ⁇ ] is usually carried out at -20 to 60 ° C, preferably 0 to 30 ° C when ⁇ is a chlorine atom.
  • the reaction time is usually about 1 to 24 hours, preferably about 2 to 12 hours.
  • Reaction [A] can usually be carried out in the presence of a dehydrating condensing agent and a solvent when Z is —OH.
  • Dehydrating condensation agents include carbodiimides such as ⁇ , ⁇ '-dicyclohexylcarbodiimide, 1,3 diisopropylcarbodiimide, 1-ethyl 3- (3 dimethylaminopropyl) carbodiimide hydrochloride; 1,1, -carbohydrate -Rubis 1H-imidazole, phosphoric acid diester ester phosphate, Jetylphosphorus Russia-Dart 1,3,5 Triaza 2,4,6-Triphospholine 2,2,4,4,6,6 Hexachloride, cyanuric Chloride, isobuty chloroformate Chlorosulfuryl isocyanate, trifluoroacetic anhydride and the like.
  • carbodiimides such as ⁇ , ⁇ '-dicyclohexylcarbodiimide, 1,3 diisopropylcarbodiimide, 1-ethyl 3- (3 dimethylaminopropyl) carbodiimide hydrochloride; 1,1, -
  • any solvent may be used as long as it is inert to the reaction.
  • etherols such as diethyl ether, butyl ether, tetrahydrofuran, dioxane, dimethoxyethane; halogenated compounds such as black benzene, dichlorobenzene, dichloromethane, chlorophenol, carbon tetrachloride, dichloroethane, trichloroethane, dichloroethylene Hydrocarbons; aromatic hydrocarbons such as benzene, toluene, xylene; acetonitryl, propio-tolyl, ⁇ , ⁇ ⁇ ⁇ ⁇ dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, dimethylacetamide, ⁇ —Polar aprotic solvents such as methylpyrrolidone; esters such as methyl acetate, ethyl acetate, propyl
  • the reaction [ ⁇ ] can usually be carried out at 20 to 60 ° C, preferably 0 to 30 ° C, when ⁇ is ⁇ .
  • the reaction time is usually about 0.5 to 24 hours, preferably about 1 to 12 hours.
  • Reaction [A] is usually performed in the presence of a base and a solvent when Z is C alkoxy.
  • Bases include alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium tertiary butoxide; trimethylamine, triethylamine and triisopropyl.
  • One or two or more tertiary amines such as 1,8 diazabicyclo [5.4.0] 17 undecene and 1,4 diazabicyclo [2.2.2] octane can be appropriately selected.
  • the base can be used in an amount of 1 to 5 times mol, preferably 1 to 2.5 times mol, of the compound of formula (II).
  • Any solvent may be used as long as it is inert to the reaction.
  • diethyl ether, butyl ether, tetrahydrofuran, dioxane, dimethoxy ester Ethers such as tan
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • One or more polar aprotic solvents such as cetamide and ⁇ ⁇ ⁇ -methylpyrrolidone
  • alcohols such as methanol, ethanol, propanol, normal butanol, and tert-butanol can be appropriately selected.
  • Reaction [A] is usually 0 to 120 ° C, preferably 20 to 80 when Z is C alkoxy.
  • the reaction time is usually about 0.5 to 24 hours, preferably about 1 to 12 hours.
  • each of the compounds of formula (II) or formula (III) is a known compound, or can be prepared according to known materials.
  • the compound of formula (II) can be prepared according to the method described in Synthesis, 1980, page 505 or a modification thereof, and the compound of formula (III) is described in schemes 9-22 in WO 03Z24222 Can be produced according to the method described above.
  • reaction [B] can usually be carried out in the presence of a solvent.
  • any solvent may be used as long as it is inert to the reaction.
  • etherols such as diethyl ether, butyl ether, tetrahydrofuran, dioxane, dimethoxyethane; halogenated compounds such as black benzene, dichlorobenzene, dichloromethane, chlorophenol, carbon tetrachloride, dichloroethane, trichloroethane, dichloroethylene Hydrocarbons; aromatic hydrocarbons such as benzene, toluene, xylene; acetonitryl, propio-tolyl, ⁇ , ⁇ -dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, dimethylacetamide,
  • polar aprotic solvents such as ⁇ ⁇ ⁇ -methylpyrrolidone.
  • the reaction can be carried out usually at 0 to 120 ° C
  • the compound of the formula (IV) can be produced according to a known compound or a known document.
  • the compound of the formula (IV) can be prepared by the method described in Org. Prep. Proceed. Int., 1993, 25, 585, the method described in schemes 8 to 10 in WO03Z24222 or the like. Can be manufactured.
  • the compound (VII) is obtained by converting pyrrole and a 2-chloropyridine derivative (VI), for example, when J is a chlorine atom, Usually, it can manufacture by making it react in presence of a base.
  • the solvent used in the reaction include aromatic hydrocarbons such as benzene, toluene, and xylene, acetonitrile, propio-tolyl, ⁇ , ⁇ -dimethylformamide, dimethylsulfoxide, and hexamethylphosphoric triamide.
  • Polar aprotic solvents and mixtures thereof are examples of the solvent used in the reaction.
  • the base used in the reaction for example, one or more kinds of alkali metal carbonates such as sodium carbonate and potassium carbonate, alkali metal hydrides such as sodium hydride and potassium hydride, and the like are appropriately used. You can choose.
  • the base can be used in an amount of 1 to 2 moles, preferably 1 to 1.2 moles per mole of pyrrole.
  • the reaction temperature in step 1-1 of reaction [C] is usually 20 to 100 ° C, preferably 40 to 70 ° C.
  • the reaction time is usually about 2 to 12 hours, preferably about 3 to 6 hours.
  • the compound (VII) can be isolated, for example, by performing a post-treatment operation by the following method (1) or (2).
  • isolated compound (VII) can be further purified by operations such as chromatography and recrystallization. It can be refined.
  • step 12 of reaction [C] compound (VIII) is produced by carrying out a Vilsmeier reaction with respect to compound (VII) and introducing a formyl group at the 2-position of pyrrole. This comes out.
  • step 1-3 of reaction [C] compound (IX) can be produced by reacting compound (VIII) with a halogenating agent.
  • a halogenating agent when an equimolar amount of the compound (VIII) is used as the halogenating agent, a compound in which any one of R 3 , R 4 or R 5 is halogen is obtained.
  • the halogenating agent is used in an amount twice or more the amount of Compound (VIII), a compound in which any two of R 3 , R 4 and R 5 are halogens is formed.
  • Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether, and tert-butyl methyl ether, acetonitrile, propio-tolyl, ⁇ , ⁇ ⁇ ⁇ ⁇ dimethylformamide, dimethyl sulfoxide, and hexamethylphosphoric triamide.
  • Polar aprotic solvents such as and mixtures thereof.
  • examples of the halogenating agent used in the reaction include N-nitrocarboxylic acid amides such as N-chlorosuccinimide, N-bromosuccinimide, and N-dosuccinimide.
  • the reaction temperature in step 1-3 of reaction [C] is usually 0 to 100 ° C, preferably 30 to 70 ° C.
  • the reaction time is usually about 2 to 48 hours, preferably about 3 to 12 hours.
  • step 1-4 of reaction [C] compound (Ilia) can be produced by reacting compound (IX) with an oxidizing agent.
  • the reaction is usually performed in the presence of water and an organic solvent.
  • the solvent used in the step 1-4 of the reaction [C] include ethers such as tetrahydrofuran, ethyleneglycolinoresmethinoleatenore, tert-butinoremethinoleatenore; alcohols such as tert-butanol Polar aprotic solvents such as acetonitrile, propio-tolyl, ⁇ , ⁇ -dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, and mixtures thereof.
  • examples of the oxidizing agent used in step 1-4 of the reaction [C] include metal oxidizing agents such as chromic anhydride and potassium permanganate, and halohalates such as sodium chlorite.
  • metal oxidizing agents such as chromic anhydride and potassium permanganate
  • halohalates such as sodium chlorite.
  • halite salts are used as oxidizing agents
  • halogen scavengers such as chilly 2-butene!
  • the halo of 5-position of pyrrole occurs simultaneously with the acid of aldehyde to carboxylic acid.
  • the reaction temperature is usually 0 to 80 ° C, preferably 20 to 40 ° C.
  • the reaction time is usually about 10 to 96 hours.
  • a compound (II lb) in which X is a nitrogen atom and Z is —OH can be produced by the following reaction [D] (wherein , J is a halogen).
  • step 3-1 of reaction [E] compound (XV) is produced by reacting an aline derivative (XIV) with 2,5 dimethoxytetrahydrofuran usually in the presence of a solvent.
  • a solvent used in the reaction include aromatic hydrocarbons such as benzene, toluene and xylene; alcohols such as methanol and ethanol; organic acids such as acetic acid and propionic acid; acetonitrile, propio-tolyl, ⁇ , ⁇ — And polar aprotic solvents such as dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, and mixtures thereof.
  • 2,5-Dimethoxytetrahydrofuran can be usually used in an amount of 1.5 to 2 moles compared to the phosline derivative (XIV).
  • the reaction temperature is usually 20 to 150 ° C, preferably 70 to 100 ° C.
  • the reaction time is usually about 2 to 12 hours, preferably about 3 to 6 hours.
  • step 3-2 of reaction [E] compound (XVI) is reacted by using compound (XV) in place of compound (VII) in the same manner as in step 12 of reaction [C]. Can be manufactured.
  • step 3-3 of reaction [E] compound (XVII) is reacted in the same manner as in step 13 of reaction [C] using compound (XVI) instead of compound (VIII). Can be manufactured.
  • step 3-4 of reaction [E] compound (IIIc) is prepared in the same manner as in step 1-4 of reaction [C], except that compound (XVII) is used instead of compound (IX). Produced by reacting It can be done.
  • R 3 may be substituted with formyl or alkoxy !, iminoalkyl, alkylamino, or may be substituted with dialkylamino, iminoalkyl or
  • the compound (Illd) which is an alkenyl substituted with 1 or 2 cyano groups, X is a nitrogen atom, and Z is —OH, can be produced by the following reaction [F] (wherein Hal is a halogen, and each of R and R 8 is a hydrogen atom or C alkyl).
  • step 41 of reaction [F] compound (XVIII) is reacted in the same manner as in step 13 of reaction [C] using compound (VII) instead of compound (VIII). Can be manufactured.
  • step 4-2 of reaction [F] when R 8 is a hydrogen atom, compound (XIX) is replaced with compound (VII) in the same manner as in step 12 of reaction [C]. It can be produced by reacting with compound (XVIII). And when R 8 is C alkyl,
  • Compound (XVIII) is mixed with an appropriate acid chloride or acid anhydride under the Friede Crafts reaction conditions. It can be produced from a kit that can be reacted with a salt.
  • step 43 of the reaction [F] the compound (XX) is obtained by converting the compound (XIX) into a tertiary amine as a scavenger for carbon monoxide, alcohol as a nucleophile and acid generated in the system.
  • a transition metal catalyst such as palladium or cobalt and a phosphine ligand.
  • methanol which includes methanol, ethanol, propanol and the like, is desirable.
  • the tertiary amines used are trimethylamine, triethylamine, triisopropylamine, diisopropylpropylamine, pyridine, 4 dimethylaminopyridine, 2,6 dimethylviridine, 4-pyrrolidinopyridine, N-methylmorpholine, ⁇ , ⁇ ⁇ ⁇ ⁇ Dimethylaniline, ⁇ , ⁇ ⁇ Jetyl-Arine, ⁇ ⁇ -Ethyl ⁇ -Methyl-Arine, 1,8 Diazabicyclo [5.4.0] 1-7 Decene, 1,4 Diazabicyclo [2.2.2] Octane .
  • Examples of the solvent used in the reaction include polar aprotic solvents such as ⁇ , ⁇ ⁇ ⁇ ⁇ dimethylformamide, dimethyl sulfoxide, and ⁇ -methylpyrrolidone.
  • polar aprotic solvents such as ⁇ , ⁇ ⁇ ⁇ ⁇ dimethylformamide, dimethyl sulfoxide, and ⁇ -methylpyrrolidone.
  • a combination of palladium acetate and diphenylphosphinopropane is desirable.
  • the reaction is usually carried out at 25 to 120 ° C, preferably 50 to 70 ° C.
  • the reaction time is usually about 1 to 24 hours, preferably about 3 to 7 hours.
  • the compound of the formula (XX) can be produced according to known literature.
  • the compound (XX) can be produced according to the method described in Tetrahedron Letters, 1992, page 33, pages 1959-1962, or the like.
  • step 4-4 of reaction [F] when R 3 is an iminoalkyl group optionally substituted with alkoxy, it can be produced by the following reaction [G] (wherein R and R 8 Each is a hydrogen atom or C alkyl, R 9 is C alkyl, and J is halogen)
  • the compound (XXII) can be produced by reacting the compound (XX) with a 0-alkylhydroxylamine mineral salt in the presence of a base group, usually using a solvent.
  • a base group usually using a solvent.
  • the base include one or more of alkali metal carbonates such as sodium carbonate and potassium carbonate; alkali metal acetates such as sodium acetate; tertiary amines such as trimethylamine and triethylamine. Can be appropriately selected.
  • the base can be used in an amount of 1 to 4 moles, preferably 1.1 to 2.2 moles to the compound (XX).
  • the solvent any solvent inert to the reaction may be used.
  • ethers such as jetyl ether, butinoreethinoreethenole, tetrahydrofuran, dixanthane, dimethoxyethane;
  • Halogenated hydrocarbons such as mouth benzene, dichlorobenzene, dichloromethane, black mouth form, carbon tetrachloride, dichloroethane, trichloroethane, dichloroethylene; aromatic hydrocarbons such as benzene, toluene, xylene; methanol, ethanol
  • One or more alcohols can be appropriately selected from such alcohols.
  • the reaction temperature is usually 25 to 120 ° C, preferably 50 to 80 ° C.
  • the reaction time is usually about 1 to 12 hours, preferably about 3 to 7 hours.
  • step 4-4 of reaction [F] when R 3 is an iminoalkyl group which may be substituted with alkylamino or dialkylamino, it can be produced by the following reaction:
  • R and R 8 is a hydrogen atom or C alkyl, and R 9 is C alkyl.
  • Compound (XXIV) is the above compound (XX) and alkyl hydrazine! / Can be produced by reacting N, N dialkylhydrazine in a solvent, usually in the presence of an acid catalyst.
  • the acid catalyst to be used include inorganic acids such as hydrochloric acid and sulfuric acid; organic acids such as acetic acid and p-toluenesulfonic acid.
  • the solvent any solvent inert to the reaction may be used.
  • ethers such as jetyl ether, butyl ether, tetrahydrofuran, dioxane, dimethoxyethane; black benzene, dichlorobenzene, Halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, dichloroethane, trichloroethane, dichloroethylene; aromatic hydrocarbons such as benzene, toluene and xylene; alcohols such as methanol and ethanol One type or two or more types can be appropriately selected.
  • the reaction temperature is usually 10 to 120 ° C, preferably 50 to 80 ° C.
  • the reaction time is usually about 30 minutes to 8 hours, preferably about 1 to 4 hours.
  • step 44 of reaction [F] when R 3 is an alkenyl group substituted with one cyano group, it can be produced by the following reaction [I] (wherein R And each of R 8 is a hydrogen atom or C alkyl).
  • Bases used include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; sodium hydride and potassium hydride and the like.
  • Alkali metal hydrides trimethylamine, triethylamine, triisopropylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, 2,6 dimethylpyridine, 4-pyrrolidinopyridine, N-methylmorpholine, ⁇ , ⁇ Tertiary amines such as dimethylaniline, ⁇ , ⁇ jetylaniline, ⁇ ethyl ⁇ -methylaniline, 1,8 diazabicyclo [5.4.0] 7 undecene, 1,4-diazabicyclo [2.2.2] octane; ⁇ -butyllithium
  • alkyllithiums can be appropriately selected.
  • any solvent may be used as long as it is inert to the reaction.
  • ethers such as jetyl ether, butyl ether, tetrahydrofuran, dioxane and dimethoxyethane; benzene, toluene, Aromatic hydrocarbons such as xylene; 1 or 2 from halogenated hydrocarbons such as black benzene, dichlorobenzene, dichloromethane, black mouth form, carbon tetrachloride, dichloroethane, trichloroethane, dichloroethylene, etc. More than one species can be selected as appropriate.
  • the reaction temperature is usually ⁇ 10 to 100 ° C., desirably 20 to 50 ° C.
  • the reaction time is Usually, it is about 1 to 36 hours, preferably about 5 to 12 hours.
  • step 44 of reaction [F] when R 3 is an alkenyl group substituted with two cyano groups, it can be prepared by the following reaction CF] (wherein R and R Each of R 8 is a hydrogen atom or C alkyl).
  • Compound (XXVIII) can be produced by reacting the compound (XX) and malononitrile with a solvent in the presence of a base.
  • Bases used include piperidine, trimethylamine, triethylamine, triisopropylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, 2,6 dimethylviridine, 4 pyrrolidinopyridine, ⁇ —
  • Organic bases such as methyl morpholine, ⁇ , ⁇ ⁇ ⁇ ⁇ dimethylaniline, ⁇ , ⁇ ⁇ cetylaniline, ⁇ ethyl ⁇ -methylaline; ammonium acetate, acetic acid salts such as sodium acetate; sodium methoxide, It can be appropriately selected from sodium alkoxides such as sodium ethoxide.
  • ethers such as jetinoreethenore, butinoreethinoreatenore, tetrahydrofuran, dioxane, dimethoxyethane; benzene; 1 type or 2 or more types can be suitably selected from aromatic hydrocarbons such as toluene and xylene; alcohols such as methanol, ethanol and propanol; carboxylic acids such as formic acid and acetic acid.
  • the reaction temperature is usually ⁇ 10 to 100 ° C., desirably 20 to 50 ° C.
  • Reaction time is usually 1 The time is about 36 hours, preferably about 5-12 hours.
  • step 45 of reaction [F] (or steps 45a to 45d of reaction [G] to i), compound (Hid) is obtained by mixing compound (XXI) in an ordinary solvent. It can be produced by hydrolysis using potassium trimethylsilanolate. Any solvent may be used as long as it is inert to the reaction. For example, ethers such as jetyl ether, butyl ether, tetrahydrofuran, dioxane, and dimethoxyethane; benzene, toluene In addition, one or more aromatic hydrocarbons such as xylene can be appropriately selected.
  • the reaction temperature is usually 10 to 80 ° C, preferably 20 to 40 ° C.
  • the reaction time is usually about 3 to 48 hours, preferably about 8 to 15 hours.
  • the pest control agent containing the compound of the present invention includes, for example, various pest control agents that are problematic in the field of agriculture and horticulture, that is, agricultural and horticultural pest control agents, and pest control agents parasitic on animals, that is, animals. It is particularly useful as a parasite control agent.
  • Pesticides for agricultural and horticultural use include, for example, power useful as insecticides, acaricides, nematicides, and soil-killing insecticides.
  • Namihada, -Senamihada, Kanzahadada, Mikanhada Plant parasites such as apple hada, chinodokorida, mandarin orange, mite, etc .; koga, weevil, lotus root, codling moth, ball worm, tobacco bad worm, maiiga, kono noiga, chinokokakumon hamaki, apple kokukakumon amaki , Momoshin Taiga, Nashihime Shinchii, Tamanayaga, Power Braga, Colorado potato beetle, Urihamushi, Ballui bilville, Aphids, Pruners, leafhoppers, scale insects, stink bugs, whiteflies, thrips, beetles, beetles Such as moss, ants, and clams Agricultural
  • Stomach pests such as gastropods, isopods such as bark beetles, staghorns, etc .; Sanitary pests such as house dust mites, house flies, mosquito power, cockroaches, etc .; Bataga, Azuki beetle, Kokunosutomodoki, Goomushimodashi Stored pests such as moss; clothing, house pests such as Iga, Himekatsubushimushi, termites, etc .; It is effective for controlling ticks.
  • the agricultural and horticultural pest control agent containing the compound of the present invention is particularly effective for controlling plant parasitic mites, agricultural pests, plant parasitic nematodes and the like.
  • the agricultural and horticultural pesticide containing the compound of the present invention is also effective for controlling various resistant pests against drugs such as organic phosphorus agents, carbamate agents, and synthetic pyrethroid agents.
  • drugs such as organic phosphorus agents, carbamate agents, and synthetic pyrethroid agents.
  • the compound of the present invention has excellent osmotic transfer properties, soil harmful insects, mites, and wire can be obtained by treating the soil with an agricultural and horticultural pesticide containing the compound of the present invention. At the same time as controlling insects, gastropods, and isopoda, it can also control pests on the foliage.
  • Another desirable aspect of the pest control agent containing the compound of the present invention is to comprehensively control the plant parasitic mites, agricultural pests, plant parasitic nematodes, gastropods, soil pests, etc. Agricultural and horticultural pest control agents.
  • the agricultural and horticultural pest control agent containing the compound of the present invention is usually a powder, granule, granule wettable powder, wettable powder, aqueous suspension, oily mixture of the compound and various agricultural adjuvants. Used in various forms such as suspensions, aqueous solvents, emulsions, solutions, pastes, aerosols, and microdispersions. Needless to say, the present invention can be applied to any formulation form commonly used in the art as long as it meets the purpose of the present invention.
  • Adjuvants used in the formulation include diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaolin, bentonite, kaolinite and sericite, clay, sodium carbonate, sodium bicarbonate, sodium sulfate, zeolite, starch, etc.
  • Solid carrier water, toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, black benzene, cyclohexane, dimethyl sulfoxide, ⁇ , ⁇ -dimethylformamide, dimethylacetamide, ⁇ — Methyl-2-pyrrolidone, alcohol and other solvents; fatty acid salts, benzoates, alkylsulfosuccinates, dialkylsulfosuccinates, polycarboxylates, alkyl sulfates, alkyl sulfates, alkylaryl sulfates, alkyl disulfates Glycol ether sulfate , Alcohol sulfate, alkyl sulfonate, alkyl aryl sulfonate, aryl sulfonate, lignite sulfonate, alkyl diether ether dis
  • each component of these adjuvants can be used by appropriately selecting one or two or more types without departing from the object of the present invention.
  • they can be appropriately selected from those known in the art, for example, extenders, thickeners, anti-settling agents, antifreeze agents, dispersion stabilizers, phytotoxicity reductions.
  • Various commonly used adjuvants such as agents and fungicides can also be used.
  • the compounding ratio of the compound of the present invention and various adjuvants is 0.001: 99.999 to 95: 5, preferably 0.005: 99.995 to 90:10.
  • the application of the agricultural and horticultural pest control agent containing the compound of the present invention cannot be defined unconditionally due to differences in weather conditions, formulation, application time, application location, pest type and occurrence. However, it is generally carried out at an active ingredient concentration of 0.05 to 800,000 ppm, preferably 0.5 to 500,000 ppm, and the application amount per unit area is 0.05 to 50000 g, preferably 1 to 30000 g, of the present compound per hectare.
  • pest control containing the compound of the present invention The application of the pest control agent for agricultural and horticultural use, which is another desirable embodiment of the pesticide, is performed according to the application of the pest control agent.
  • the present invention also includes a method for controlling harmful organisms by such an application method, particularly a method for controlling plant parasitic mites, agricultural pests, and plant parasitic nematodes.
  • the pesticide for agricultural and horticultural use containing the compound of the present invention can be used in combination with or combined with other agricultural chemicals, fertilizers, safeners, etc. May show sex.
  • Other pesticides include herbicides, insecticides, acaricides, nematicides, soil pesticides, fungicides, antiviral agents, attractants, antibiotics, plant hormones, plant growth regulators, etc. It is done.
  • a mixed pest control composition in which the compound of the present invention and one or more active compound compounds of other agricultural chemicals are used in combination or in combination is preferred in terms of application range, timing of chemical treatment, control activity, etc. It is possible to improve.
  • the compound of the present invention and the other active ingredient compounds of other agricultural chemicals may be used separately by mixing them at the time of spraying, or may be used by preparing both together.
  • the present invention also includes such a mixed pest control composition.
  • the mixing ratio between the compound of the present invention and the active ingredient compound of other agricultural chemicals cannot be defined unconditionally due to differences in weather conditions, formulation form, application time, application location, pest type and occurrence, etc. 300 to 300: 1, preferably 1: 100 to 100: 1.
  • the appropriate amount to be applied is 0.1 to 50000 g, preferably 1 to 30000 g as the total amount of active ingredient compounds per hectal.
  • the present invention also includes a method for controlling pests by a method for applying such a mixed pest control composition.
  • insecticides as an active ingredient compound (generic name; including some pending applications) of insecticides, acaricides, nematicides or soil insecticides, that is, pest control agents, for example, profenofos ( Profenofos, Cyclonorevos, Dichlorvos, Fenamithion, Fenitrothion, EPN, Diazinon, Chlorpyrif os-methyl, Acephate, Prothiofos, Phostiazate Fosth iazate), Phosphocarb, Phosphocarb, Cadusafos, Disulfoton, Chlorpyrifos, Demeton-S-methyl, Dimethoate, Memethamidophos (Methamidophos) Phosphate ester compounds; Power barbaryl, Propoxur, Aldicarb, Carboforan Carno carbs such as Thiodicarb, Methomyl, Oxamyl, Ethiof
  • microbial pesticides such as BT agents, entomopathogenic virus agents, entomopathogenic fungi agents, nematode pathogenic fungi agents, avermectin, emamectin-benzoate, minolebemectin ( Milbemectin), Spinosad, Ivermectin, Lepimectin, and other natural products such as Azadirachtin can be mixed and used together.
  • Examples of the animal parasite control agent include ectoparasites that parasitize on the body surface of the host animal (back, armpit, lower abdomen, inner thigh, etc.) and the host animal body (stomach, intestine, lungs, It is effective for the control of endoparasites parasitic on the heart, liver, blood vessels, subcutaneous, lymphoid tissue, etc., but it is particularly effective for the control of ectoparasites.
  • ectoparasites include animal parasitic mites and fleas. These types are very difficult to list, so here are some examples.
  • Examples of animal parasitic mites include Boophilus microplus, Rnipicephalus sanguineus, Haemaphvsalis longicorni s, and Tematani (Haemaphvsalis flava) campanula ta, chair power (Haemaphvsalis concinna), hamatophvsalis iap onica, sinker "Haemaphvsalis ias, mite (Ixodes ovatus, tick) Ticked ticks (Ixodes persulcatus), Takasago Kiraramagii (Amblvomma testudinarium), gifted Togenamatani (Haemaphvsalis megaspinosa), Amamikakumaguji (Dermacentor r eticulatus); Trisanta-(Ornithonvssus no, Na Trisanta- (
  • Ornithonvssus bursa such as: Eutrombicula wic hmanni, Leptotrombidium akamushi, Leptotrom bidium pallidum, Leptotrombidiumizii, Nepto autumnalis), American claw beetle (Eutrombicula alfreddugesi), crested moths of Heelenicula mivagawai: Insid ticks (Chevletiella vasguri), Ragwort ticks (Chevletiella m rasitivorax), ev Rotifer mite (Psoroptes cuniculi), Cyprioptes bovis, Otodectes cvnotis, Hydra mite (Sarcoptes scabiei), Rotifer mite (Notoedres cati) canis )
  • Bida the animal parasite control agent containing the compound of the present invention is particularly effective for controlling ticks and the like.
  • Examples of fleas include ectoparasite worms belonging to the order Flea (Siphonaptera), more specifically fleas belonging to the family Flea (Pulicidae), Cleaphyllus (Ceratephyllus), etc. .
  • Examples of fleas belonging to the family Fleas include: Fleafish (CtenoceDhalides cams), Catnocephalides (Ctenocephalides felis), Humanfish (Pulex irritans), -Echidnoph aga gallinacea, Examples include animal worms (Leptopsvl la segnis), Nosopsyllus fasciatus, Monopsvll us mik, etc.
  • animal parasite control agents containing the compounds of the present invention Is effective for the control of fleas belonging to the family Flea, especially ini fleas and cat fleas.
  • ectoparasites include, for example, lice such as white lice, white lice, hedge lice, white lice, white lice; white lice such as white lice; blood sucking such as Usiab, Uinu power, and Thmetgebu Diptera pests.
  • endophytic organisms include nematodes such as lungworms, bench beetles, tuberous worms, gastric parasites, roundworms, and filamentous worms; Crustacea, multi-headed tapeworms, single-banded tapeworms, multi-banded tapeworms; Japanese schistosomiasis, fluke-like fluke; kokujimu, malaria parasite, intestinal floriformus, toxoplasma Protozoa such as Cryptosporidium.
  • nematodes such as lungworms, bench beetles, tuberous worms, gastric parasites, roundworms, and filamentous worms
  • Crustacea multi-headed tapeworms, single-banded tapeworms, multi-banded tapeworms
  • Japanese schistosomiasis fluke-like fluke
  • kokujimu malaria parasite, intestinal floriformus, toxoplasma Protozoa such as Cryptosporidium.
  • Examples of host animals include various pet animals, livestock, poultry, and the like, and more specifically, dogs, cats, mice, rats, hamsters, guinea pigs, squirrels, rabbits, ferrets, birds (for example, , Pigeons, omme, nine-birds, wild birds, parakeets, pine pine, canary, etc.), sushi, horses, butter, hidge, ducks, etc.
  • the animal parasite control agent containing the compound of the present invention is effective for the control of pests parasitic on pet animals or livestock, particularly ectoparasites. It is especially effective for dogs, cats, ushi or horses in pets or livestock.
  • the compound of the present invention when used as an animal parasite control agent, it may be used as it is. Also, powders, granules, tablets, powders, capsules, liquid agents, emulsions, aquatic compounds with appropriate adjuvants. It can also be formulated and used in various forms such as a suspension and an oily suspension.
  • any conventional dosage form used in the art can be used as long as it is suitable for the purpose of the present invention.
  • the adjuvant used in the preparation include anionic surfactants and nonionic surfactants exemplified as the aforementioned preparation adjuvants for agricultural and horticultural pest control agents such as cetyltrimethylammonium bromide.
  • Cationic surfactants water, acetone, acetonitrile, monomethylacetamide, dimethylacetamide, dimethylformamide, 2-pyrrolidone, N-methyl-2-pyrrolidone, kerosene, triacetin, methanol, ethanol, isopropanol , Benzenoreanoleconole, Ethylene glycol, Propylene glycol, Polyethylene glycol, Liquid polyoxyethylene glycol nore, Butinoresin glycol nore, Ethylene glycol nole monomethinoatenore, Ethyleneglycoleno monoethylenoatenore, Diethylene glycol Solvents such as ricinole monoethylenoate, diethylene glycol normal butyl ether, dipropylene glycol monomethyl ether, dipropylene glycol normal butyl ether; butylhydroxyl-sol, butyhydroxytoluene, ascorbic acid, sodium metabisulfite
  • auxiliary agents can be used by appropriately selecting from those known in the field, and further, selected from various auxiliary agents used in the above-mentioned agricultural and horticultural fields. You can also
  • the compounding ratio of the compound of the present invention and various adjuvants is usually about 0.1: 99.9 to 90:10. In actual use of these preparations, use them as they are or dilute them to a predetermined concentration with a diluent such as water, and add various spreading agents (surfactants, vegetable oils, mineral oils, etc.) as necessary. It can be used as a supplement.
  • a diluent such as water
  • various spreading agents surfactants, vegetable oils, mineral oils, etc.
  • Administration of the compound of the present invention to a host animal is performed orally or parenterally.
  • oral administration methods include tablets, liquids, capsules, and drugs containing the compound of the present invention.
  • examples include methods of administering hearth, biscuits, minced meat, and other feeds.
  • parenteral administration method for example, the compound of the present invention is prepared in an appropriate formulation and then taken into the body by intravenous administration, intramuscular administration, intradermal administration, subcutaneous administration, etc .; spot-on
  • the dose of the compound of the present invention to the host animal varies depending on the administration method, administration purpose, disease symptoms, etc., it is usually O.Olmg to: L00g to the body weight lKg of the host animal, preferably 0.1 It is appropriate to administer at a rate of mg to 1 Og.
  • the present invention also includes a method for controlling pests by the administration method or dosage as described above, particularly a method for controlling ectoparasites or endoparasites.
  • the present invention by controlling animal parasitic pests as described above, there are cases where various diseases of host animals caused by them can be prevented or treated.
  • the present invention includes a prophylactic or therapeutic agent for parasite-derived animal diseases comprising the compound of the present invention as an active ingredient, and a method for preventing or treating parasite-derived animal diseases.
  • the compound of the present invention when used as an animal parasite control agent, various vitamins, minerals, amino acids, nutrients, enzyme preparations, antipyretic agents, sedatives, anti-inflammatory agents, bactericides, and coloring agents together with adjuvants. , Fragrances, preservatives and the like can be mixed or used together. If necessary, mix with or use other animal drugs and pesticides such as anthelmintics, anti-coxime, insecticides, acaricides, fleas, nematicides, bactericides, and antibacterials. In this case, the effect may be even better.
  • the present invention includes a mixed pest control composition in which various components as described above are mixed or used together, and a pest control method using the composition, particularly control of ectoparasites or endoparasites. A method is also included.
  • N-bromosuccinimide 7. lg was added little by little to a mixed solution of 7.5 g of the target product obtained in the above step (2) and 100 ml of dimethylformamide, and then heated to 70 ° C. Reacted for hours. After completion of the reaction, the mixed solution was ice-cooled and a saturated aqueous sodium hydrogen carbonate solution was added. After extraction twice with ethyl acetate, the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel chromatography (eluent: n-hexane Z ethyl acetate 3Z 1).
  • Test example 1 Effectiveness test for Lotus monto
  • Cabbage leaf pieces were dipped in a chemical solution prepared so that the concentration of the compound of the present invention was 50 ppm or 12.5 ppm for about 10 seconds and air-dried.
  • a wet filter paper was laid on a petri dish with a diameter of 9 cm, and air-dried cabbage leaves were placed on it. There, 10 larvae of 2 to 3 years old were released, and then they were covered and left in a constant temperature room at 25 ° C. On the 5th day after release, mortality was determined, and the mortality rate was calculated using the following formula. Abnormal insects were also considered dead.
  • the compound Nos. 2 to 9, 11 to 14, 16 to 21, 24 to 26 and 43 were determined to have a mortality rate of 50 ppm, and all compounds showed a high control effect of 90% or more. When the death rate was determined at 12.5 ppm for Compound No.l, it showed a high control effect of 90% or more. It was.
  • Corrected rollover rate (%) [(Non-rollover rate of control zone Non-rollover rate of treatment zone) Non-rollover rate of Z zone] X 100
  • Treatment with the compounds of the present invention overturns most juvenile ticks.
  • 0.5 ml of an acetone solution of the compound of the present invention prepared to 10.6 ppm is dropped into a glass tube (inner diameter 2.6 cm, bottom area 5.3 cm 2 , height 12 cm) with a smooth bottom.
  • Acetone is evaporated at room temperature to form a dry film containing the compound of the present invention on the bottom surface.
  • Ten cat fleas (C tenocephalides felis) adults are placed therein and the compound of the present invention is exposed. The test will be conducted in triplicate.
  • the above is uniformly mixed to form a powder.
  • the mixture of the above components and the compound of the present invention are mixed at a weight ratio of 4: 1 to obtain a wettable powder.
  • the above is uniformly mixed and pulverized to obtain an aqueous suspension.
  • the above ingredients are mixed uniformly to form a solution.
  • the novel anthranilamides have been found to have a very high control effect against pests at a low dose, and pest control agents containing these compounds are, for example, agricultural products. It can be used as a control agent for various pests that are problematic in the horticulture field, that is, a pesticide for agricultural and horticultural use, and a pest control agent that parasitizes animals, that is, an animal parasite.

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  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
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Abstract

Durant des années, une grande variété d'agents pesticides a été employée, lesdits agents présentant des défauts ne pouvant pas être passés sous silence, tels qu'une très faible efficacité. Il existe donc un besoin de développer des agents pesticides ne présentant pas de tels défauts. La présente invention décrit des composés d’anthranylamide de formule : (I) où R1 représente un atome d'halogène ou un groupement alkyle ; R2 représente un atome d'hydrogène, un atome d'halogène, un groupement alkyle, etc. ; chacun des groupements R3, R4 et R5 représente un atome d'hydrogène, un atome d'halogène, un groupement alkyle, etc. ; R6 représente un atome d'halogène, un groupement alkyle ou un groupement halogénoalkyle ; A représente un atome d'hydrogène, un groupement alkyle, un groupement alkylthioalkyle, un groupement halogénoalkylthioalkyle, un groupement alkylsulfinylalkyle, un groupement halogénoalkylsulfinylalkyle, un groupement alkylsulfonylalkyle, un groupement halogénoalkylsulfonylalkyle, ou un groupement (cycloalkyle en C3-C4)-alkyle éventuellement substitué ; et X représente CR7 ou un atome d'azote.
PCT/JP2006/309025 2005-05-02 2006-04-28 Composé de type anthranylamide, méthode de synthèse dudit composé et agent pesticide contenant ledit composé WO2006118267A1 (fr)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012007500A3 (fr) * 2010-07-15 2012-03-29 Bayer Cropscience Ag Nouveaux composés hétérocycliques servant d'agents de lutte contre les nuisibles
TWI422329B (zh) * 2006-12-14 2014-01-11 Ishihara Sangyo Kaisha 含有協同性有效量的鄰胺苯醯胺化合物及其它殺蟲劑和/或殺真菌劑之農藥組成物

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003528070A (ja) * 2000-03-22 2003-09-24 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 殺虫性アントラニルアミド類
WO2004067528A1 (fr) * 2003-01-28 2004-08-12 E.I. Du Pont De Nemours And Company Insecticides a base de cyano-anthranilamide

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003528070A (ja) * 2000-03-22 2003-09-24 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 殺虫性アントラニルアミド類
WO2004067528A1 (fr) * 2003-01-28 2004-08-12 E.I. Du Pont De Nemours And Company Insecticides a base de cyano-anthranilamide

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI422329B (zh) * 2006-12-14 2014-01-11 Ishihara Sangyo Kaisha 含有協同性有效量的鄰胺苯醯胺化合物及其它殺蟲劑和/或殺真菌劑之農藥組成物
US8729106B2 (en) * 2006-12-14 2014-05-20 Ishihara Sangyo Kaisha, Ltd. Pesticidal compositions
US9737074B2 (en) 2006-12-14 2017-08-22 Ishihara Sangyo Kaisha, Ltd. Pesticidal compositions
US10039284B2 (en) 2006-12-14 2018-08-07 Ishihara Sangyo Kaisha, Ltd. Pesticidal compositions
WO2012007500A3 (fr) * 2010-07-15 2012-03-29 Bayer Cropscience Ag Nouveaux composés hétérocycliques servant d'agents de lutte contre les nuisibles
US9233951B2 (en) 2010-07-15 2016-01-12 Bayer Intellectual Property Gmbh Heterocyclic compounds as pesticides

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