WO2007116949A1 - Procédé servant à protéger une plante - Google Patents

Procédé servant à protéger une plante Download PDF

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Publication number
WO2007116949A1
WO2007116949A1 PCT/JP2007/057699 JP2007057699W WO2007116949A1 WO 2007116949 A1 WO2007116949 A1 WO 2007116949A1 JP 2007057699 W JP2007057699 W JP 2007057699W WO 2007116949 A1 WO2007116949 A1 WO 2007116949A1
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group
halogen atom
plant
optionally substituted
substituted
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PCT/JP2007/057699
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English (en)
Japanese (ja)
Inventor
Norihisa Sakamoto
Masato Konobe
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Sumitomo Chemical Company, Limited
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Publication of WO2007116949A1 publication Critical patent/WO2007116949A1/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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products

Definitions

  • the present invention relates to a plant protection method, and more particularly to a plant protection method from harm by pests.
  • GB 1324293, US 4170657 and US 4243680 describe N′-methylbenzoylurea compounds methylated at the N ′ position.
  • N, monomethyl benzoylurea compound represented by the following formula (I) or a salt thereof is the root or seed of a plant, or a plant It was found that by applying to the root zone of the plant, the plant can be protected from harm by pests, and the present invention has been reached.
  • the present invention is as follows.
  • X represents a fluorine atom or a chlorine atom
  • R 1 is a hydrogen atom, a C 1 -C 6 alkyl group which may be substituted with a halogen atom, a C 2 -C 6 alkenyl group which may be substituted with a halogen atom, a C 2 -C 6 alkynyl group, C 6— C 14 aryl group, C 7— C 11 aralkyl group, C 2—C 6 alkoxy alkyl group, C 7— C 14 aryl alkyl group, C 3—C 6N, N-di (alkyl) amino alkyl group, C 2 — C 6 alkylthioalkyl group, C2 1 C 6 alkylsulfinylalkyl group, C 2 -C 6 alkylsulfonyl alkyl group, C 3— C 9 alkoxy alkoxy alkylyl group, C 2—C 6 alkoxy carbon group Ponyl group, C 8— C 12 aralkyloxycarbonyl group, N, N—
  • R 3 may be a halogen atom, a CI-C4 alkyl group that may be substituted with a halogen atom, a C 1 C4 alkoxy group that may be substituted with a halogen atom, or a halogen atom.
  • n one of integers from 0 to 4.
  • R 1 is a hydrogen atom
  • R 3 is a halogen atom
  • C 1 may be substituted with a halogen atom
  • C 1 may be substituted with a C 4 alkoxy group or a halogen atom
  • a plant protectant from pests containing this compound or a salt thereof and an inert carrier.
  • R 1 is a hydrogen atom and R 3 is a halogen atom, which may be substituted with a halogen atom C 1 C 1 alkoxy group which may be substituted with a C 4 alkoxy group or a halogen atom —C 4 alkyl group, and m is 0 or 1 ( ⁇ ′—methyl)
  • a benzoylurea compound or a salt thereof and an inert carrier 5.
  • a plant protective agent from harm by pests.
  • Examples of the C 1 -C 6 alkyl group optionally substituted by a halogen atom include a methyl group, a chloromethyl group, a difluoromethyl group, a trichloromethyl group, an ethyl group, a 2-bromoethyl group, 2, 2, 2-trifluor.
  • Examples of the C 2 -C 6 alkenyl group which may be substituted with a halogen atom include a vinyl group, a 1-propenyl group, a 2-propenyl group, an isopropenyl group, a 2-butenyl group, and an isobutenyl group.
  • Group, and 3,3-dichloro-2-propenyl group, and C 2 -C 6 alkynyl group includes, for example, echelle group, 2-propynyl group and 1-propynyl group,
  • Examples of the C 6 -C 14 aryl group include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, and a biphenylyl group,
  • Examples of the C 7 -C 11 aralkyl group include a benzyl group and a phenethyl group,
  • Examples of the C 2 -C 6 alkoxyalkyl group include a methoxymethyl group, an ethoxymethyl group, a 1-propoxymethyl group, a 2-methoxyethyl group, a 2-ethoxyethyl group, a 3-methoxypropyl group, and a 3-ethoxypropyl group.
  • Examples of the C 7 -C 14 aryloxyalkyl group include a phenoxymethyl group and a 2-phenoxychetyl group,
  • Examples of the C 3 -C 6 N, N-di (alkyl) aminoalkyl group include a dimethylaminomethyl group, a 2- (dimethylamino) ethyl group, a jetylaminomethyl group, and a 2- (jetylamino) ethyl group.
  • Examples of the C 2 _C 6 alkylthioalkyl group include a methylthiomethyl group, an ethylthiomethyl group, a 2- (methylthio) ethyl group, and a 2- (ethylthio) ethyl group.
  • W 200 Examples of the C 2 _C 6 alkylthioalkyl group include a methylthiomethyl group, an ethylthiomethyl group, a 2- (methylthio) ethyl group, and a 2- (ethylthio) ethyl group.
  • Examples of the C 2 -C 6 alkylsulfinylalkyl group include a methylsulfinylmethyl group, an ethylsulfiermethyl group, a 2- (methylsulfier) ethyl group, and a 2- (ethylsulfiel) ethyl group,
  • Examples of the C 2 -C 6 alkylsulfonylalkyl group include a methylsulfonylmethyl group, an ethylsulfonylmethyl group, a 2- (methylsulfonyl) ethyl group, and a 2- (ethylsulfonyl) ethyl group,
  • Examples of the C 3 -C 9 alkoxyalkoxyalkyl group include (2-methoxyethoxy) methyl group,
  • Examples of the C 2 -C 6 alkoxycarbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, a normal propoxycarbonyl group, an isopropoxycarbonyl group, a normal butoxycarbonyl group, and a tert-butoxycarbonyl group.
  • Examples of the C 8 -C 12 aralkyloxycarbonyl group include a benzyloxycarbonyl group,
  • N, N-di (C 1 -C 6 alkyl) strong rubamoyl groups examples include dimethylcarbamoyl and jetylcarbamoyl,
  • Examples of the C 2 -C 6 alkylcarbonyl group optionally substituted with a halogen atom include an acetyl group, a propionyl group, a trifluoroacetyl group, and a chloroacetyl group,
  • Examples of the C 1 -C 5 alkylsulfonyl group optionally substituted with a halogen atom include a methanesulfonyl group, an ethanesulfonyl group, and a trifluoromethanesulfonyl group,
  • Examples of the C 6 -C 10 arylaryl group include a benzenesulfonyl group and a toluenesulfonyl group.
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • Examples of the C1-C4 alkyl group which may be substituted with a halogen atom include a methyl group, a chloromethyl group, a difluoromethyl group, a trichloromethyl group, a trifluoromethyl group, an ethyl group, a 2-bromoethyl group, 2, 2 , 2-Trifluoroethyl group, Pentafluoroethyl group, Propyl group, 3, 3, 3-Trifluoropropiyl Group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group and 4,4,4-trifluorobutyl group,
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • Examples of the C 1 -C 4 alkyl group optionally substituted with a halogen atom include a methyl group, a chloromethyl group, a difluoromethyl group, a trichloromethyl group, a trifluoromethyl group, an ethyl group, a 2-bromoethyl group, and 2, , 2-Trifluoroethyl group, Penufluoroethyl group, Propyl group, 3, 3, 3-Trifluoropropyl group, Isopropyl group, Butyl group, Isobutyl group, sec-butyl group, tert-butyl group and 4, 4 , 4 trifluorobutyl group,
  • Examples of the C 1 -C 4 alkoxy group optionally substituted with a halogen atom include a methoxy group, an ethoxy group, a 1-propyloxy group, an isopropoxy group, a tert-butoxy group, a difluoromethoxy group, and a trifluoro group.
  • Examples of the C 2 -C 6 alkoxyalkoxy group optionally substituted with a halogen atom include 2-trifluoromethoxy-1,1,2-trifluoroethoxy group,
  • Examples of the C 2 -C 4 alkenyloxy group optionally substituted with a halogen atom include a 2-propenyloxy group and a 3,3-dichloro-2-propenyloxy group,
  • Examples of the C 2 -C 4 alkynyloxy group which may be substituted with a halogen atom include a 2-propynyloxy group.
  • This compound is capable of forming an acid addition salt in which a basic group such as a dialkylamino group in a substituent in the molecule can be agrochemically acceptable with an inorganic acid or an organic acid.
  • Examples of the inorganic acid addition salt of the compound include hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid, phosphoric acid, and perchloric acid, and examples of the organic acid addition salt of the compound include Formic acid, acetic acid, propionic acid, succinic acid, succinic acid, benzoic acid, p-toluenesulfonic acid, meta And salts with sulfonic acid and trifluoroacetic acid. Next, the synthesis method of this compound is shown.
  • This compound can be produced, for example, by the following (Synthesis Method 1) to (Synthesis Method 4).
  • the reaction is usually performed in a solvent.
  • Examples of the solvent used in the reaction include ketones such as acetone and methyl ethyl ketone, aromatic hydrocarbons such as benzene, toluene, and xylene, aliphatic hydrocarbons such as hexane and heptane, jetyl ether, tetrahydrofuran, 1 , 4-dioxane, 1,2-dimethoxyethane, ethers such as 1,2-diethoxyethane, halogenated hydrocarbons such as chloroform, benzene, dichlorobenzene, nitriles such as acetonitril, N, N —Dimethylformamide, N, N-dimethylase And aprotic polar solvents such as toamide, 1-methyl-2-pyrrolidone, 1,3-dimethylimidazolinone, dimethyl sulfoxide, water, and mixtures thereof.
  • ketones such as acetone and methyl ethyl ket
  • the amount of the compound represented by the formula (III) used in the reaction is usually 0.5 to 2 mol relative to 1 mol of the compound represented by the formula (II).
  • the reaction temperature is usually in the range of -78 to 150, and the reaction time is usually in the range of 0.1 to 100 hours.
  • the reaction mixture is poured into water, extracted with an organic solvent, and then subjected to post-treatment operations such as drying and concentration of the organic layer, whereby the compound represented by the formula (1-1) is obtained.
  • the compound represented by the formula (1-1) can be isolated.
  • the isolated compound represented by the formula (1-1) can be further purified by recrystallization, column chromatography or the like.
  • R 1 — 1 is a C 1 C 6 alkyl group which may be substituted with a halogen atom, and is substituted with a halogen atom.
  • the reaction is usually performed in a solvent in the presence of a base.
  • Examples of the solvent used in the reaction include ketones such as acetone and methyl ethyl ketone, aromatic hydrocarbons such as benzene, toluene and xylene, aliphatic hydrocarbons such as hexane and heptane, jetyl ether, and tetrahydrofuran.
  • 1,4-dioxane 1,2-dimethoxyethane, ethers such as 1,2-diethoxyethane, halogenated hydrocarbons such as chloroform, benzene and dichlorobenzene, nitriles such as acetonitrile and nitrile, N , N-dimethylformamide, N, N-dimethylacetamide, 1-methyl-2-pyrrolidone, 1,3-dimethylimidazolinone, dimethylsulfoxide, and other aprotic polar solvents, water, and mixtures thereof.
  • Examples of the base used in the reaction include hydroxides of alkali metal or alkaline metal such as sodium hydroxide, lithium hydroxide, calcium hydroxide, sodium hydride, potassium hydride, hydrogenation.
  • Alkali metals such as calcium or alkali earth metal hydrides, alkali metals such as sodium carbonate or potassium carbonate, or alkaline earth metal carbonates, sodium ethylate, sodium methylate, etc.
  • organic bases such as tributylamine, pyridine, 1,8-diazapicyclo [5,4,0] undecene (hereinafter abbreviated as DBU), and the like.
  • the amount of the reagent used in the reaction can be used in an excess amount when using a reagent that is liquid under the reaction conditions, but usually the formula (IV) is added to 1 mol of the compound represented by formula (IV).
  • the compound represented by III) is 1 to 4 moles, and the base is 1 to 4 moles.
  • the reaction temperature is usually in the range of 1 78 to 15 50, and the reaction time is usually in the range of 0.1 to 20 hours.
  • the reaction mixture is poured into water, extracted with an organic solvent, and then subjected to post-treatment operations such as drying and concentration of the organic layer, whereby the compound represented by the formula (1-2) is obtained.
  • the compound represented by the formula (1-2) can be isolated.
  • the isolated compound represented by the formula (1-2) can be further purified by recrystallization, column chromatography or the like.
  • R 1 - 2 is optionally substituted with a halogen atom C 1-C 6 alkyl group, substituted with a halogen atom C 2—C 6 alkenyl group, C 2—C 6 alkynyl group, C 7—C 11 aralkyl group, C 2—C 6 alkoxyalkyl group, C 7—C 14 allyloxyalkyl group, C 3—C 6 N, N—di (alkyl) aminoalkyl group, C 2—C 6 alkyl thioalkyl group, C 2—C 6 alkylsulfinylalkyl group, C 2 -C 6 alkylsulfonylalkyl group, C 3 -C 9Alkoxyalkoxyalkyl group, C 2 —C 6 alkoxycarbonyl group, C 8 -C 12 aralkyloxycarbonyl group, N, N—di (di-6-al
  • the compound represented by the formula is a compound represented by the formula (1-1) and the formula (V)
  • L 1 is a halogen atom (e.g., chlorine atom and bromine atom), methanesulfonyl O alkoxy group, benzenesulfonyl O alkoxy group, toluene sulfonyl O alkoxy group, Represents a methoxysulfonyloxy group or an oxysulfonyloxy group; ]
  • halogen atom e.g., chlorine atom and bromine atom
  • the reaction is usually performed in a solvent in the presence of a base.
  • Examples of the solvent used in the reaction include ketones such as acetone and methyl ethyl ketone, aromatic hydrocarbons such as benzene, toluene and xylene, aliphatic hydrocarbons such as hexane and heptane, jetyl ether, tetrahydrofuran, 1 , 4-dioxane, ethers such as 1,2-dimethoxyethane, 1,2-diethoxyethane, halogenated hydrocarbons such as chloroform, chlorobenzene, and dichlorobenzene, nitriles such as acetonitrile, N, N —Dimethylformamide, N, N-dimethyla
  • Examples include aprotic polar solvents such as cetamide, 1-methyl-2-pyrrolidone, 1,3-dimethylimidazolinone and dimethyl sulfoxide, water, and mixtures thereof.
  • Examples of the base used in the reaction include alkali metal or alkaline earth metal hydroxides such as sodium hydroxide, hydroxy hydroxide, calcium hydroxide, and alkali such as sodium hydride, potassium hydride, and calcium hydride.
  • Organic lithium such as normal butyl lithium and lithium diisopropylamide and organic bases such as triethylamine, pyridine and DBU.
  • the amount of the reagent used in the reaction can be used in an excess amount when a reagent that is liquid under the reaction conditions is used, but usually the amount is 1 mol of the compound represented by the formula (1-1).
  • the compound represented by formula (V) is in a ratio of 1 to 4 mol, and the base is in a ratio of ⁇ to 4 mol.
  • the reaction temperature is usually in the range of ⁇ 78 to 1550, and the reaction time is usually in the range of 0.1 to 1 hour.
  • the reaction mixture is poured into water, extracted with an organic solvent, and then subjected to post-treatment operations such as drying and concentration of the organic layer, whereby the compound represented by the formula (1-3) is obtained.
  • the compound represented by the formula (1-3) is obtained.
  • the isolated compound represented by the formula (I 13) can be further purified by recrystallization, column chromatography or the like.
  • L 2 represents a halogen atom (for example, a chlorine atom, an iodine atom, and an iodine atom). ]
  • the reaction is usually performed in a solvent in the presence of a base.
  • Examples of the solvent used in the reaction include ketones such as acetone and methyl ethyl ketone, aromatic hydrocarbons such as benzene, toluene, and xylene, aliphatic hydrocarbons such as hexane and heptane, jetyl ether, tetrahydrofuran, 1 , 4-Dioxane, 1,2-Dimethoxyshetane, Ethers such as 1,2-Diethoxyethane, Halogenated hydrocarbons such as Chromium Form, Chromatic Benzene, and Dichlorobenzene, Nitriles such as Acetitonitrile, N, Aprotic polar solvents such as N-dimethylformamide, N, N-dimethylacetamide, 1-methyl-2-pyrrolidone, 1,3-dimethylimidazolinone, dimethyl sulfoxide, water, and mixtures thereof.
  • ketones such as acetone and methyl ethyl ketone
  • Examples of the base used in the reaction include sodium hydroxide, potassium hydroxide, hydrogenated hydroxide of alkaline metal or alkaline metal such as sodium hydroxide, lithium hydroxide, calcium hydroxide, and the like.
  • Alkali metal such as calcium or alkali earth metal hydride, alkali metal such as sodium carbonate or potassium carbonate or carbonate of alkaline earth metal, sodium ethylate, sodium methylate, etc.
  • Organic lithium such as alcoholate, normal butyl lithium, lithium diisopropylamide, and organic bases such as triethylamine, diisopropylethylamine, pyridine, DBU, and the like.
  • the amount of the reagent used in the reaction may be an excess amount when using a reagent that is liquid under the reaction conditions.
  • the compound 1 represented by the formula (VI I) is used.
  • the proportion of the compound represented by the formula (VI) is 1 to 4 mol and the base is 1 to 4 mol with respect to mol.
  • the reaction temperature is usually in the range of ⁇ 78 to 180 ° C.
  • the reaction time is usually in the range of 0.1 to 200 hours.
  • the reaction mixture is poured into water, extracted with an organic solvent, and then subjected to post-treatment operations such as drying and concentration of the organic layer, whereby the compound represented by the formula (1-2) is obtained.
  • the compound represented by the formula (1-2) is obtained.
  • the isolated compound represented by the formula (I 12) can be further purified by recrystallization, column chromatography or the like. Next, a reference synthesis method of a synthetic intermediate of this compound will be shown.
  • It can be produced by reacting a compound represented by the above formula with a polyalkylalkoxysilane compound and a chlorocarbonylating agent.
  • the reaction is usually performed in a solvent in the presence of a base.
  • Examples of the solvent used in the reaction include ketones such as acetone and methyl ethyl ketone, aromatic hydrocarbons such as benzene, toluene and xylene, aliphatic hydrocarbons such as hexane and heptane, jetyl ether, tetrahydrofuran, 1 , 4-dioxosan, ethers such as 1,2-dimethoxyethane, 1,2-diethoxyethane, halogenated hydrocarbons such as chloroform, chlorobenzene, dichlorobenzene, nitriles such as acetonitrile, N, N —Aprotic polar solvents such as dimethylformamide, N, N-dimethylacetamide, 1-methyl-1-2-pyrrolidone, 1,3-dimethylimidazolinone, dimethyl sulfoxide, water, and mixtures thereof.
  • ketones such as acetone and methyl ethyl ketone
  • Examples of the base used in the reaction include sodium hydroxide, potassium hydroxide, hydrogenated hydroxide of alkaline metal or alkaline metal such as sodium hydroxide, lithium hydroxide, calcium hydroxide, and the like.
  • Alkali metals such as calcium or alkali earth metal hydrides, alkali metals such as sodium carbonate and potassium carbonate W or alkaline earth metal carbonates, alkali metal alcoholates such as sodium edylate and sodium methylate, organic lithiums such as normal butyl lithium and lithium diisopropylamide, and organic bases such as triethylamine, pyridine and DBU .
  • trialkylchlorosilane compound used in the reaction examples include trimethylchlorosilane and triethylchlorosilane.
  • chlorocarbonylating agent used in the reaction examples include phosgene, trichloromethyl chloroformate, and bis (trichloromethyl) carbonate.
  • the amount of the reagent used in the reaction is usually 1 to 4 moles of the trialkylchlorosilane compound, 1 to 4 moles of the chlorocarbonylating agent to 1 mole of the compound represented by the formula ( ⁇ ⁇ ),
  • the base is usually in a proportion of 1 to 4 mol.
  • the reaction temperature is usually in the range of ⁇ 78 to 150 ° C.
  • the reaction time is usually in the range of 0.1 to 200 hours.
  • the compound represented by the formula (IV) can be isolated by performing post-treatment operations such as concentrating the reaction mixture as it is.
  • the isolated compound represented by the formula (IV) can be used in the next step without purification.
  • R 1 1 represents the same meaning as described above.
  • the reaction is usually performed in a solvent in the presence of a base.
  • Examples of the solvent used in the reaction include ketones such as acetone and methyl ethyl ketone, aromatic hydrocarbons such as benzene, toluene, and xylene, aliphatic hydrocarbons such as hexane and heptane, jetyl ether, tetrahydrofuran, 1, 4—Zoki Sun, ethers such as 1,2-dimethoxyethane and 1,2-diethoxyethane, halogenated hydrocarbons such as chloroform, chlorobenzene and dichlorobenzene, nitriles such as acetonitrile, N, N-dimethyl
  • Examples include aprotic polar solvents such as formamide, N, N-dimethylacetamide, 1-methyl-2-pyrrolidone, 1,3-dimethylimidazolinone and dimethyl sulfoxide, water, and mixtures thereof.
  • Examples of the base used in the reaction include hydroxides of alkali metal or alkaline metal such as sodium hydroxide, lithium hydroxide, calcium hydroxide, sodium hydride, potassium hydride, hydrogenation.
  • Alkali metals such as calcium or alkali earth metal hydrides, alkali metals such as sodium carbonate or potassium carbonate, or alkaline earth metal carbonates, sodium ethylate, sodium methylate, etc.
  • Organic lithium such as normal butyl lithium and lithium diisopropylamide, and organic bases such as triethylamine and DBU.
  • an excess amount of (X) can be used as the base.
  • the amount of the reagent used in the reaction is 1 to 6 moles of the compound represented by formula (X) and 1 to 6 moles of the base, based on 1 mole of the compound represented by formula (IX).
  • the reaction temperature is usually in the range of ⁇ 78 to 1550, and the reaction time is usually in the range of 0.1 to 2200 hours.
  • the compound represented by the formula (VI I) is isolated by performing post-treatment operations such as pouring the reaction mixture into water, extracting with an organic solvent, and then drying and concentrating the organic layer. can do.
  • the isolated compound represented by the formula (VI I) can be further purified by recrystallization, column chromatography or the like. (Reference Synthesis Method 3)
  • the compound represented by the formula (IX) can be produced by reacting the compound represented by the formula (I I I) with a chlorocarbonylating agent.
  • the reaction is usually performed in a solvent in the presence of a base.
  • Examples of the solvent used in the reaction include ketones such as acetone and methyl ethyl ketone, aromatic hydrocarbons such as benzene, toluene and xylene, aliphatic hydrocarbons such as hexane and heptane, jetyl ether, tetrahydrofuran, 1 , 4 dioxosan, ethers such as 1,2-dimethoxyethane, 1,2-diethoxyethane, Halogenated hydrocarbons such as roloform, black benzene, dichlorobenzene, nitriles such as acetonitrile, N, N-dimethylformamide, N, N-dimethylacetamide, 1-methyl-2-pyrrolidone, 1,3-dimethylimidazolinone And aprotic polar solvents such as dimethyl sulfoxide, water, and mixtures thereof.
  • ketones such as acetone and methyl ethyl ketone
  • Examples of the base used in the reaction include sodium hydroxide, alkaline hydroxide, calcium hydroxide, and other hydroxides of alkaline metals or alkaline metals, hydrogen sodium, potassium hydride, hydrogen Alkali metals such as calcium hydroxide or alkali earth metal hydrides, alkali metals such as sodium carbonate and potassium carbonate, or alkaline earth metal carbonates, sodium ethylate, and alkali metals such as sodium methylate
  • organic bases such as triethylamine, pyridine, DBU and the like and organic lithiums such as alcoholate, normal butyl lithium and lithium diisopropylamide.
  • chlorocarbonylating agent used in the reaction examples include phosgene, trichloromethyl chloroformate, bis (trichloromethyl) carbonate, and the like.
  • the amount of the reagent used in the reaction is usually 1 to 4 moles of the chlorocarbonylating agent and 1 to 4 moles of the base, based on 1 mole of the compound represented by the formula (I II).
  • the reaction temperature is usually in the range of 78 to 150 ° C, and the reaction time is usually in the range of 0.1 to 200 hours.
  • the compound represented by the formula (IX) is isolated by performing post-treatment operations such as pouring the reaction mixture into water, extracting with an organic solvent, and then drying and concentrating the organic layer. be able to.
  • the isolated compound represented by the formula (IX) can be further purified by column chromatography or the like.
  • the compound represented by the formula (IX) can also be isolated by performing post-treatment operations such as concentrating the reaction mixture as it is.
  • the compound produced by the above synthesis method is further known per se, for example, alkylation, alkenylation, alkynylation, acylation, amination, sulfidation, sulfinylation, sulfonation, oxidation, reduction, halogenation.
  • the substituent can be converted into other desired substituents by nitration or the like.
  • m is 0 or 1 (N, —methyl) benzoylurea compound;
  • X is a fluorine atom ( ⁇ '-methyl) benzoylurea compound
  • X is a chlorine atom ( ⁇ '-methyl) benzoylurea compound
  • R 1 is a hydrogen atom ( ⁇ '—methyl) benzoylurea compound
  • R 3 is a halogen atom, a C 1-C 4 alkoxy group which may be substituted with a halogen atom or a C 1-C 4 alkyl group which may be substituted with a halogen atom ( ⁇ '-methyl) benzoylurea compound ;
  • R 3 is a halogen atom, a C 1 -C 4 alkoxy group which may be substituted with a halogen atom, or a C 1 C 4 alkyl group which may be substituted with a halogen atom, and m is 0 or 1 ( ⁇ '—methyl) benzoylurea compound;
  • R 1 is a hydrogen atom
  • R 3 is a halogen atom, which may be substituted with a halogen atom, or a single C 4 alkoxy group or a C 1 -C 4 alkyl group which may be substituted with a halogen atom, ( ⁇ '-methyl) benzoylurea compound in which m is 0 or 1.
  • the plant protective agent of this invention contains this compound or its salt, and an inert carrier.
  • the inert carrier include a solid carrier, a liquid carrier, and an ointment base.
  • the plant protective agent of the present invention is usually further formulated with an emulsifier, a suspending agent, a spreading agent, a penetrating agent, a wetting agent, a mucilage agent, a stabilizer, and the like into a suitable form.
  • an emulsifier emulsions, liquids, microemulsions, emulsions, floorables, oils, wettable powders, aqueous solvents, sols, powders, granules, fine granules, microcapsules, tablets Ointments, capsules, pellets, poisonous baits, sprays, aerosols, coatings and the like.
  • the present compound or a salt thereof is usually 0.1 to 80% by weight, preferably Is contained in an amount of about 1 to 80% by weight.
  • the plant protective agent of the present invention is an emulsion, solution, wettable powder or the like
  • the present compound or a salt thereof is usually from 0.;! To 80% by weight, preferably from 10 to
  • this compound or a salt thereof is usually contained in an amount of about 0.1 to 50% by weight, preferably about 1 to 20% by weight.
  • the present compound or a salt thereof is usually contained in an amount of about 0.1 to 50% by weight, preferably about 0.1 to 20% by weight.
  • solid carriers examples include vegetable powders (soybean powder, tobacco powder, wheat flour, wood powder, etc.), mineral powders (clays such as kaolin, bentonite, and acid clay), talc powder, mouth Talc such as limestone powder and silica such as diatomaceous earth and mica powder), alumina, sulfur powder, activated carbon, calcium carbonate, ammonium sulfate, sodium hydrogen carbonate, lactose, urea and the like.
  • vegetable powders such as kaolin, bentonite, and acid clay
  • talc powder such as limestone powder and silica such as diatomaceous earth and mica powder
  • alumina sulfur powder
  • activated carbon calcium carbonate
  • ammonium sulfate sodium hydrogen carbonate
  • lactose lactose
  • urea examples of solid carriers
  • liquid carrier examples include water, alcohols (methyl alcohol, ethyl alcohol, n-propyl alcohol, isopropyl alcohol, ethylene glycol, etc.), ketones (acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexane).
  • alcohols methyl alcohol, ethyl alcohol, n-propyl alcohol, isopropyl alcohol, ethylene glycol, etc.
  • ketones acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexane
  • ethers tetrahydrofuran, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, etc.
  • aliphatic hydrocarbons kerosene, fuel oil, machine oil, etc.
  • aromatic hydrocarbons toluene
  • Xylene solvent naphtha, methyl naphthalene, etc.
  • halogenated hydrocarbons diichloromethane, black mouth form, carbon tetrachloride, etc.
  • acid amides N, N-dimethylformamide, N, N— Mechirua acetamide, etc.
  • N- methylpyrrolidone N- methylpyrrolidone
  • esters acetate Echiru acetate heptyl, fatty acid glycerol esters, such as ⁇ one butyrolactone
  • nitriles such as ⁇ Se Tonitoriru, such as propionic nitrile
  • one or more of these liquid carriers can be used in combination at an appropriate ratio.
  • ointment base materials include polyethylene glycol, pectin, polyhydric alcohol esters of higher fatty acids (such as glyceryl monostearate), cell mouth derivatives (such as methylcellulose), sodium alginate, bentonite, higher alcohols, many Examples include monohydric alcohols (such as glycerin), petrolatum, white petrolatum, liquid paraffin, lard, various vegetable oils, lanolin, dehydrated lanolin, hardened oil, and resins.
  • one or more of these ointment bases can be blended at an appropriate ratio.
  • a surfactant can be further added to the plant protection agent of the present invention as necessary.
  • Surfactants used in such cases include, for example, sarcophagus, polyoxyethylene alkyl aryl ethers [for example, Neugen (trade name) 1 * 1 1 4 2 (EA 1 4 2 (trade name) ); Manufactured by Daiichi Kogyo Seiyaku Co., Ltd.
  • alkyl sulfates e.g., Emar 10 (trade name), emal 40 (trade name); Kao Corporation
  • alkylbenzene sulfonates e.g., neogen (trade name), neogen T (Trade name); Daiichi Kogyo Seiyaku Co., Ltd., Neoperex (trade name); Kao Co., Ltd.
  • polyethylene glycol ethers [For example, Nonipole 8 5 (Product name), Nonipole 1 0 0 (Product name) , Nonipol 1 6 0
  • the plant protective agent of the present invention includes other insecticides (for example, pyrethroid insecticides, organophosphorus insecticides, carbamate insecticides, neonicotinoid insecticides, natural insecticides).
  • insecticides for example, pyrethroid insecticides, organophosphorus insecticides, carbamate insecticides, neonicotinoid insecticides, natural insecticides.
  • fungicides eg copper fungicides, organochlorine fungicides, organosulfur fungicides, phenols (Bactericides), synergist
  • Fenothiocarb Fenoxycarb, fenoxycarb, furathiocarb, isoprocarb (isoprocarb: MIPC), metolcarb, methomyl (me thorny 1), methiocarb, comfort, oxamyl, pirimi curve (pirimicurve) , Propoxur (PHC), XMC, thiodicarb, xylylcarb, etc .; (3) Synthetic pyrethroid compounds ''
  • Phenylpyrazole compounds Acetoprole, fipronil, vaniliprole, pyriprole, pyrafluprole, etc .; (8) B-toxin insecticide
  • Avermectin— B cyenopyrafen, bromopropylate, buprofezin, chlorphenapyr, cyenopyrafen>cyromazine> D— D (1, 3- Dichloropropene, emamectin-benzoate;, fenazaquin, flepirazo, phos (f lupyrazofos, hydroprene), indoxacarb> lepimectin, metoxadiazon ), Milbemycin-A, pymetrozine, pyridalyl, pyriproxyfen u) yriproxyfen), spinosad, sulfluramid, tolfenpyrad, triazemate , Flubendiamide, cyflumet E emissions (cyf lumetofen), arsenic trioxide (Arsenic acid), Benku opening Chiazu (benclothiaz), lime room search (Calc
  • R 1 is Me, C 1, Br or F
  • R 2 is F, Cl, Br, CI-C4 haloalkyl, or C1-C4 haloalkoxy
  • R 3 is F, C 1 or Br
  • R 4 is H, one or more halogen atoms; CN; SMe; S ( ⁇ ) Me; S (0) 2 Me and optionally substituted with OMe C 1 mono C4 alkyl, C3—C 4 Alkenyl, C3-C4 alkynyl, C3-C5 cycloalkylalkyl, or C4-C6 cycloalkylalkyl,
  • R 5 is H or Me
  • R 6 is H, F or C 1
  • R 7 represents H, F or C 1.
  • an active ingredient of an acaricide for example,
  • Acequinosyl (aceQuinocyl), amitraz, benzoximate, bromopropylate, quinomethionate (chinomethionat), chlorobenzi late, CPCBS (chlorfenson), clofentezine, kelofol, etoxazole, fenbutatin oxide, fenothiocarbmate, fenpyroxycarbate (Fenpyroximate), flucrypyrim (fluacrypyrim), fullproxyfen (uproxyfen), hexythiazox, propargite (BPPS), polynactins (polynactins), pyridaben, pyrimidifen, pyrimidifen (Tebufenpyrad), tetradifon (spirodiclofen), amidofurmet (amidof lumet), etc.
  • nematicide for example,
  • Triclamide tricyclazole, triridemorph ⁇ triflumizole (tr.iflumizole), trifloxystrobin, triforine, triticonazole, validamycin, vinclozoline (Vinclozolin), piniconazole, zineb, ziram, syosensamide (zoxamide), and herbicide active ingredients and Z or plant growth regulators include, for example, abscisic acid ( Abscisic acid), Asetokuroru (acetochlor), reed full Orff-ene (acif luor fen-sod ium) 3 ⁇ 4 Arakurore (alachlor Arokishijimu (alloxydim), Ametorin (ametryn), amicarbazone (amicarbazone), amidosulfuron
  • flufenacet flufenpyr, flumetralin, flumioxazin, full-propanate sodium
  • inabenfide Indole acetic acid (IAA), Indole butyric acid (Indole butyric acid), iodosulfuron, ioxynil-octanoate, isouron, isoxachlortole, isoxadifen, isoxadifen, karbutilate, lactofen Lenacil, linuron, LGC-42153 (LGC-42153), maleic hydrazide, mecoprop (MCPP), MCP salt (2-Methyl-4-chlorophenoxyacetic acid) salts), MC PA ⁇ thioethyl, MCPB (2-methy 1 -4-ch 1 or ophenoxybutanoic acid ethyl ester), mefenacet, mefluidide (mefluidide unepiquat), Mesosulfuron, mesotrione, methyl daimuron, metolachlor, metribuzin, mets
  • P uniconazole-P
  • pernaredo vemolate: PPTC
  • frucetosulfuron f lucetosulfuron
  • Orthosulfanuron ort hosulfanuron, pinoxaden, pyrasul fotole, tefuryltrione, tempotrione (tembotrione), and thiencarbazone methyl, for example.
  • benoxanol benoxacor
  • cloquintocet-mexyl Cyometrinil
  • daimuron dichlormid
  • the content of these active ingredients in the plant protection agent of the present invention is usually 1 to 80% by weight, preferably 1 About 20% by weight.
  • the content of the above-mentioned insecticide, herbicide, acaricide and additives other than Z or fungicide in the plant protective agent of the present invention depends on the type and content, or the dosage form of the preparation. Although it is different, it is usually from about 0.000 to 99.9% by weight, preferably about 1 to 99% by weight. More specifically, the surfactant is usually 1 to 20% by weight, preferably about 1 to 15% by weight, the flow aid is about 1 to 20% by weight, a carrier (liquid carrier, solid carrier, The ointment base is usually about 1 to 90% by weight.
  • the surfactant is usually contained in an amount of about 1 to 20% by weight, preferably about 1 to 10% by weight, and about 20 to 90% by weight of water. Is preferred.
  • the plant protective agent of the present invention is an emulsion or a wettable powder (eg, a granular wettable powder)
  • it is usually diluted appropriately with water to a volume ratio of about 10 to 500 times. Used.
  • the plant protection method of the present invention is usually carried out by applying the plant protection agent of the present invention directly to the root or seed of a plant to be protected from pest damage or by applying it to the root zone of the plant.
  • the plant rhizosphere means the soil and other surrounding parts where the roots are affected.
  • Specific methods for directly applying to roots or seeds include, for example, spraying, spraying, dipping, impregnating, coating, and filming the plant protective agent of the present invention onto the roots or seeds of plants. Examples thereof include a coating method and a pellet coating method.
  • the plant protective agent of the present invention may be mixed, for example, mixed with a hydroponic liquid or mixed with a hydroponic liquid depending on the state of the rhizosphere of the plant. The method to do is mentioned.
  • planting hole treatments planting hole spraying, Planting hole treatment soil admixture, plant root treatment (stock source spraying, stock source soil mixing, stock source irrigation, late seedling season, plant source treatment), grooving treatment (planting groove spraying, grooving soil mixing), cropping treatment ( Crop spreading, Crop soil mixing, Growing season cropping), Crop treatment during sowing (Crop application during sowing, Crop soil mixing during sowing), Full treatment (spreading over the whole surface, mixing over the whole soil), etc.
  • Spraying treatment growth surface foliar spraying, under crown or around main trunk, soil surface spraying, soil surface mixing, sowing hole spraying, buttocks surface spraying, inter-plant spraying
  • other irrigation treatment such as, irrigation treatment (soil irrigation, seedling irrigation, Chemical infusion treatment, local irrigation, chemical drip irrigation, Chemigation), seedling box processing (nursing box spraying, seedling box irrigation), seedling tray processing (nursing tray spraying, seedling tray irrigation), nursery treatment (seed bed spraying, Nursery irrigation, water seedling spraying, seedling soaking), mixed soil Treatment (seedbed soil mixing, before sowing bed soil mixing), other treatment (soil mixing, plow, topsoil mixed, rain drop unit earth ⁇ sum, planting position treatment, flower cluster spraying, paste fertilizer mixing) a method for.
  • the application amount of the present compound or a salt thereof in the plant protection method of the present invention can be appropriately changed according to the application time, application place, application method, formulation form, etc., but when applied to the root zone of a plant,
  • the amount of the present compound or a salt thereof per hectare is usually about 3 to 300,000 g, preferably about 50 to 300 g, and when applied directly to the root of a plant or seed
  • the present compound or a salt thereof per one plant body or one seed of the plant is usually in a ratio of about 0.005 to 0.lg, preferably about 0.000 to 0.02 g. is there.
  • the application time of the present compound or a salt thereof is expected to be harmful to the target plant by a pest, and when the protection is performed in advance, and depending on the pest to the target plant. It can be selected as appropriate depending on the case where it is carried out for protection after the harm has been confirmed, and is not limited at all.
  • fruit vegetables such as eggplant and tomato, cabbage, lettuce, etc.
  • crops that have undergone the seedling stage such as leafy vegetables, etc.
  • the growing stage in the field is bald.
  • crops that are directly sown in normal fields, such as ivy, corn, and soybean there are, for example, the seed stage, the seeding stage in the field, and the growth stage.
  • a method of applying the present compound or a salt thereof to the rhizosphere of a plant a method of applying the present compound or a salt thereof to soil or the like after the root of the plant has developed, and the present compound or a salt thereof in advance.
  • a method of developing plant roots in the soil after applying salt to the soil and the like is mentioned.
  • the plant protection method of the present invention is generally applied to "crop". Examples of such “crop” include the following “crop”.
  • Eggplant vegetables eggplants, tomatoes, peppers, peppers, potatoes, etc.
  • cucurbitaceae vegetables brown cucumbers, capochia, zucchini, watermelon, melon etc.
  • cruciferous vegetables daikon, turnips, cirrus radish, koru rubi, Chinese cabbage) , Cabbage, mustard, broccoli, cauliflower, etc.
  • asteraceae vegetables burdock, shiyungiku, artichoke york, lettuce, etc.
  • lily family vegetables laeek, onion, garlic, asparagus, etc.
  • celery family vegetables carrot, parsley, Celery, American Bow Fu, etc.
  • Akaza vegetables Haourenso, Fudansou, etc.
  • Lamiaceae vegetables Peerilla, Mint, Basil, etc.
  • Strawberries Satsumaimo, Yamanoimo, Satoimo, etc .;
  • Berries (apples, pears, two pears, quince, quince mouth, etc.), drupes (peaches, plums, nectarines, ume, sweetweed, apricots, plums, etc.) , Grapefruit, etc.), nuts (chestnut, walnut, hazel, almond, bisyucho, cashew nut, macadamia nut, etc.), berries (blueberry, cranberry, blackberry, raspberry, etc.), grape, oyster, olive, Bean paste, banana, coffee, date palm, coconut, etc .;
  • Lawn grasses such as Noshiba, Kouraishipa, Bermudagrass, bentgrass, ryegrass, bullgrass, fescue;
  • Pastures such as ryegrass, orchardgrass, fescue, bluegrass, clover, and alfa alpha.
  • the above “crop” includes crops that have been given tolerance to herbicides by classical breeding methods, genetic recombination techniques, and the like.
  • HPPD inhibitors such as isoxaflutol
  • ALS inhibitors such as imazeupir pills and tifensulfurum methyl
  • EPSP synthase inhibitors such as imazeupir pills and tifensulfurum methyl
  • EPSP synthase inhibitors daryumin synthase inhibitors
  • Application of herbicides such as CoA carboxyxylase inhibitors; or promoxinil does not cause phytotoxicity problems.
  • crops that have been given tolerance to herbicides by classical breeding methods include Clear fi el d® canola that has been given resistance to imidazolinone herbicides; STS soybeans that have been given resistance to sulfonylurea herbicides And SR corn that has been given resistance to acetyl acetylene inhibitors.
  • a crop imparted with tolerance to a acetyl acetylene inhibitor is described in, for example, Proc. Natl. Acad. Sci. USA 1990, 87, 7175.
  • a mutant acetyl-CoA lpoxylase that develops resistance to a acetyl-CoA lpoxylase inhibitor is known, for example, from Weed Science 53: 728-746, 2005. If the gene encoding this mutant type of acetyl CoA carboxylase is introduced by genetic recombination technology, or if the gene encoding acetyl CoA carboxyxylase is introduced with a mutation related to conferring resistance to acetyl CoA carboxyxylase, Can be conferred with resistance to acetyl-CoA carboxyxylase-inhibiting herbicides.
  • crops maize varieties that have been given tolerance to Darifosarta glufosinate are known as “crops” that have been given tolerance to herbicides by genetic engineering techniques. Some of these corn varieties are sold under the trade names RoundupReady® and LibertyLink®. The above “crop” also includes crops that have been given the ability to produce insecticidal toxins by genetic engineering techniques.
  • Such insecticidal toxins include, for example, insecticidal proteins derived from Bacillus cereus and Bacillus popilie; CrylAb, CrylAc, CrylF, CrylFa2, Cry2Ab, Cry3A, Cry3Bbl or Cry9C derived from Bacillus thuringiensis, VIPK VIP2, Insecticidal protein such as VIP3 or VIP3A; Nematode-derived insecticidal protein; produced by animals such as scorpion toxin, spider toxin, bee toxin or insect-specific neurotoxin Toxins; filamentous fungi toxins; plant lectins; agglutinins; trypsin inhibitors, serine protease inhibitors, protease inhibitors such as pachintin, cisyuchin, papain inhibitors; ricin, maize RIP, abrin Ribosome-inactivating protein (RIP) such as bryodin; 3-hydroxysteroidoxidase,
  • the insecticidal toxin includes a hybrid protein of the above-mentioned insecticidal protein and a protein in which a part of amino acids constituting the above-mentioned insecticidal protein is deleted or substituted.
  • the hybrid protein is created by combining different domains of the above insecticidal protein by gene recombination technology.
  • CrylAb lacking a part of amino acids is known as a toxin lacking a part of amino acids constituting the insecticidal protein.
  • “Crops” that have been granted the ability to produce insecticidal toxins by genetic engineering techniques are resistant to attack from, for example, Coleoptera, Diptera, Z or Lepidoptera.
  • “Crops” that have been given the ability to produce insecticidal toxins through genetic engineering techniques are commercially available such as YieldGard® (a corn variety that expresses CrylAb toxin), YieldGard Rootworm® (Cry3Bbl toxin) Corn varieties), YieldGard Plus® (a corn variety that expresses CrylAb and Cry3Bbl toxins), Herculex I® (phosphinothricin N-acetyltransferase (PAT) to confer resistance to CrylFa2 toxin and glufosinate) Corn varieties that express), NuC0TN33B® (an evening varieties that express CrylAc toxin), Bol lgard I® (an evening varieties that express CrylAc toxin), Bol lgard II® (which expresses CrylA
  • Anti-pathogenic substances produced by microorganisms include, for example, PR proteins (PRPs, described in EP-A-0392 225); sodium channel inhibitors, calcium channel inhibitors (virus produced KP1, ⁇ 4, ⁇ 6 toxins, etc.) Ion channel inhibitors such as; stilbene synthase; bibenzyl synthase; chitinase; dulcanase; PR protein; peptide antibiotics, heterocyclic antibiotics; and proteins involved in plant disease resistance (Described in W0 03/000906) and the like.
  • PR proteins PRPs, described in EP-A-0392 225
  • sodium channel inhibitors such as; stilbene synthase; bibenzyl synthase; chitinase; dulcanase; PR protein; peptide antibiotics, heterocyclic antibiotics; and proteins involved in plant disease resistance (Described in W0 03/000906) and the like.
  • the plant protection method of the present invention it is possible to protect plants from harm by pests that cause harm such as feeding and sucking (for example, harmful arthropods such as harmful insects and harmful mites). Specific examples of such pests include the following.
  • Hemiptera pests Laodelphax striatellus: Nunaparvata lugens, Suna Loonfish (Sogatella furcifera), etc., Nephotettix cincticeps, Nephotettix c Aphis gossypii), Myzus persicae, Brevicoryne brassicae, Macros iphum euphorbiae ⁇ Aulacorthmn solani: Aphids such as the citrus aphid (Toxoptera ci tricidus), Nezaraantennata, Riptortus clavetus, Leptocorisa chinensis, Eysarcorisly mi st a), stink bugs such as Lygus lineolaris, whitefly (Trialeurodes vaporariorum), whiteflies such as Bemisia argentifolii, Aonidiella aurantii, San scale scale insects (Comstockaspis per
  • Nematodes Aphelenchoides besseyi, strawberry Senchu ⁇ (Nothotylenchus acris, and the like; Blattodea pests: Chiya panel cockroach (Blattella germanica), black cockroach (Periplaneta fuliginosa), Wamonkokiburi (Periplaneta americana) 3 ⁇ 4 Tohyi port cockroach (Periplaneta brunnea), oriental cockroach (Blatta orientalis) and the like; Mite order pests: Namihadani (Tetranychus urticae), Nigirihadani (Panonychus citri), Nigellanus spp., Aculops pelekassi, etc., Fushida nigiri (Polyphagotarsonemus latus), Spider mites, Crested spider mites, Tyrophagus putrescent iae, and other mites, Dermatophagoides farina
  • Ticks such as (Cheyletus moorei).
  • TMS tetramethylsilane
  • This compound (1), (2), (3), (5), (6), (7), (8), (9), (11) and (1 2) 5 mg each of Sorgen TW-20 ( Daiichi Kogyo Seiyaku Co., Ltd.) and acetone mixed solution (mixing volume ratio; Sorgen TW-20: acetone 1: 19) 0.1.
  • Dissolved in 1 ml, diluted to 3 ml with ion-exchanged water, for testing of test compounds A drug solution was prepared.
  • Cabbage seedlings were grown in a seedling container (capacity: 27 ml, height: 5.0 cm) to 2.5 leaf stage. The whole amount of the test chemical solution was irrigated on the surface of the cabbage seedling.
  • the roots of the cabbage seedlings were removed, the foliage was placed in a polyethylene cup (capacity 180 m 1), 10 second-instar larvae of Plutellaxylostella were released, and stored at 2 for an additional 7 days.
  • the cabbage seedlings were then inspected for the degree of damage caused by the diamondback larvae, comparing the case where the test compound was treated (treated area) and the case where it was not treated (untreated area). Asked. (Degree of food damage in treatment area
  • plants can be protected from harmful organisms.

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

Abstract

On peut protéger une plante contre les insectes nuisibles par application d'une quantité efficace d'un composé de N'-méthylbenzoylurée représenté par la formule (I) ou un de ses sels. à une racine, semence ou rhizosphère de la plante. (I) dans laquelle X, R1, R2, R3 et m sont semblables à leur définition dans le descriptif.
PCT/JP2007/057699 2006-04-03 2007-03-30 Procédé servant à protéger une plante WO2007116949A1 (fr)

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Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL7105350A (en) * 1971-04-21 1972-10-24 Substd benzoyl and thiobenzoyl ureas and thioureas - insecticides
JPS50105629A (fr) * 1970-05-15 1975-08-20
JPS53141242A (en) * 1977-05-13 1978-12-08 Dow Chemical Co Substitution product of *phenyl*aminocarbonyllbenzoamide
US4243680A (en) * 1979-02-07 1981-01-06 Thompson-Hayward Chemical Company Method of reducing infestation of citrus rust mites on citrus trees
JPH023659A (ja) * 1988-06-20 1990-01-09 Ishihara Sangyo Kaisha Ltd ベンゾイルウレア系化合物、それらの製造方法及びそれらを含有する有害動物防除剤
WO1997045017A1 (fr) * 1996-05-30 1997-12-04 Uniroyal Chemical Company, Inc. INSECTICIDES A BASE D'UREE BENZOYLEE AGISSANT SUR COTONNIER A BACILLUS THURINGIENSIS (Bt) MODIFIE GENETIQUEMENT
US5886221A (en) * 1997-11-03 1999-03-23 Dow Agrosciences Llc Benzoylphenylurea insecticides and methods of using certain benzoylphenylureas to control cockroaches, ants, fleas, and termites
WO1999016316A1 (fr) * 1997-09-30 1999-04-08 Uniroyal Chemical Company, Inc. Augmentation du rendement de graines de soja au moyen de benzoyluree a substitution
JP2001511786A (ja) * 1997-02-12 2001-08-14 ダウ・アグロサイエンス・エル・エル・シー 相乗作用のあるジュベノイド／キチン合成阻害剤の殺シロアリ剤組成物
WO2007046513A2 (fr) * 2005-10-20 2007-04-26 Sumitomo Chemical Company, Limited Composes de benzoyluree et utilisation

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS50105629A (fr) * 1970-05-15 1975-08-20
NL7105350A (en) * 1971-04-21 1972-10-24 Substd benzoyl and thiobenzoyl ureas and thioureas - insecticides
JPS53141242A (en) * 1977-05-13 1978-12-08 Dow Chemical Co Substitution product of *phenyl*aminocarbonyllbenzoamide
US4243680A (en) * 1979-02-07 1981-01-06 Thompson-Hayward Chemical Company Method of reducing infestation of citrus rust mites on citrus trees
JPH023659A (ja) * 1988-06-20 1990-01-09 Ishihara Sangyo Kaisha Ltd ベンゾイルウレア系化合物、それらの製造方法及びそれらを含有する有害動物防除剤
WO1997045017A1 (fr) * 1996-05-30 1997-12-04 Uniroyal Chemical Company, Inc. INSECTICIDES A BASE D'UREE BENZOYLEE AGISSANT SUR COTONNIER A BACILLUS THURINGIENSIS (Bt) MODIFIE GENETIQUEMENT
JP2001511786A (ja) * 1997-02-12 2001-08-14 ダウ・アグロサイエンス・エル・エル・シー 相乗作用のあるジュベノイド／キチン合成阻害剤の殺シロアリ剤組成物
WO1999016316A1 (fr) * 1997-09-30 1999-04-08 Uniroyal Chemical Company, Inc. Augmentation du rendement de graines de soja au moyen de benzoyluree a substitution
US5886221A (en) * 1997-11-03 1999-03-23 Dow Agrosciences Llc Benzoylphenylurea insecticides and methods of using certain benzoylphenylureas to control cockroaches, ants, fleas, and termites
WO2007046513A2 (fr) * 2005-10-20 2007-04-26 Sumitomo Chemical Company, Limited Composes de benzoyluree et utilisation

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
WELLINGA K. ET AL., JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, vol. 21, no. 3, 1973, pages 348 - 354, XP002016453 *

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