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WO2007116948A1 - Procédé servant à protéger un plante - Google Patents

Procédé servant à protéger un plante Download PDF

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Publication number
WO2007116948A1
WO2007116948A1 PCT/JP2007/057696 JP2007057696W WO2007116948A1 WO 2007116948 A1 WO2007116948 A1 WO 2007116948A1 JP 2007057696 W JP2007057696 W JP 2007057696W WO 2007116948 A1 WO2007116948 A1 WO 2007116948A1
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Prior art keywords
group
halogen atom
plant
optionally substituted
atom
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PCT/JP2007/057696
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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 WO2007116948A1 publication Critical patent/WO2007116948A1/fr

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Classifications

    • 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.
  • An object of the present invention is to provide a method for protecting plants from harm by pests.
  • the present inventors have determined that an effective amount of an N′-ethylbenzoylurea 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 and Y each represents a fluorine atom or a chlorine atom
  • R 1 is a hydrogen atom or a C 1 alkyl group optionally substituted with a halogen atom, C C 2—C 6 alkenyl, C 2—C 6 alkynyl, C6—C 14 aryl, C7—C 11 aralkyl, C2—C 6 alkoxyalkyl, C 7— C 14 aryloxyalkyl group, C3—C6N, N —di (alkyl) aminoalkyl group, C 2—C 6 alkylthioalkyl group, C2—C 6 alkylsulfinylalkyl group, C 2—C 6 alkylsulfonyl alkyl group Group, C3-C9 alkoxyalkoxyalkyl group, C2-C6 alkoxycarbonyl group, C8-C12 aralkyloxycarbonyl group, N, N-di (C1 C6 alkyl) Carpamoyl group, C 2-C 6 alkylcarbonyl group optional
  • R 2 represents a halogen atom or a C 1 -C 4 alkyl group which may be substituted with a halogen atom
  • R 3 is a halogen atom, an optionally substituted C 1 -C 4 alkyl group, an optionally substituted C 1 -C 4 alkoxy group, an optionally substituted C 2- A C6-alkoxyalkoxy group, a C2-C4 alkenyloxy group optionally substituted with a halogen atom or a C2-C4 alkynyloxy group optionally substituted with a halogen atom,
  • n one of integers from 0 to 4.
  • R 1 is a hydrogen atom
  • R 3 is a C 1 -C 4 alkoxy group which may be substituted with a halogen atom or a halogen atom, or a C 1 which may be substituted with a halogen atom
  • X and Y each represents a fluorine atom or a chlorine atom
  • R 1 is a hydrogen atom, a C 1—C 6 alkyl group optionally substituted with a halogen atom, a C 2—C 6 alkenyl group optionally substituted with a halogen atom, a C 2—C 6 alkynyl group, C 6 —C14 aryl group, C 7—C 11 aralkyl group, C2—C6 alkoxyalkyl group, C 7—C14 aryloxyalkyl group, C3—C6N, ⁇ - (alkyl) aminoalkyl group, C 2— C6 alkylthioalkyl group, C2-C6 alkylsulfinylalkyl group, C2-C6 alkylsulfonylalkyl group, C3-C9 alkoxyalkoxyalkyl group, C2-C6 alkoxycarbonyl group, C8-C 12 aralkyloxycarbonyl group, ⁇ , ⁇ -di (C1-C6 alky
  • R 3 is a halogen atom, a C 1 -C 4 alkyl group which may be substituted with a halogen atom, a C 1 -C 4 alkoxy group which may be substituted with a halogen atom, or a C 2—optionally substituted with a halogen atom.
  • n one of integers from 0 to 4.
  • R 1 is a hydrogen atom
  • R 3 is a halogen atom, a C 1 -C 4 alkoxy group that may be substituted with a halogen atom, or a C 1 that is optionally substituted with a halogen atom 1 C 4 alkyl group: ⁇
  • m is 0 or 1
  • N, —ethyl Contains a benzoylurea compound or a salt thereof and an inert carrier 5. Plant protection from harm by harmful organisms according to 5. Agent. 7. The plant protective agent according to 5. or 6, which is used for treatment of the plant rhizosphere.
  • Examples of the C 1 -C 6 alkyl group which may be substituted with a halogen atom include a methyl group, a chloromethyl group, a difluoromethyl group, a trichloromethyl group, an ethyl group, a 2-promoethyl group, and 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, 1-propenyl group, 2-propenyl group, isopropenyl group, 2-butenyl group, and isobutenyl.
  • Group and 3, 3-dichloro-2-propenyl group, and C 2 -C 6 alkynyl group includes, for example, ethynyl group, 2-propier 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 C7-C11 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-methoxy group, a 3-methoxypropyl group and a 3-ethoxypropyl group. Named,
  • Examples of the C 7- C 14 aryloxyalkyl group include a phenoxymethyl group and a 2-phenoxychetyl group,
  • Examples of the C3-C6N, N-di (alkyl) aminoalkyl group include a dimethylaminomethyl group, 2- (dimethylamino) ethyl group, jetylaminomethyl group, and 2- (jetylamino) ethyl group,
  • Examples of the C 2 -C 6 alkylthioalkyl group include a methylthiomethyl group, A ruthiomethyl 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 ethylsulfinylmethyl group, a 2- (methylsulfiel) ethyl group, and a 2- (ethylsulfinyl) 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 isopropoxy group, a normal butoxycarbonyl group, and a tert-butoxycarbonyl group.
  • Examples of the C 8 -C 12 aralkyloxycarbonyl group include a benzyloxycarbonyl group,
  • strong rubermoyl groups include dimethylcarbamoyl and jetylcarbamoyl.
  • Examples of the C 2 -C 6 alkylcarbonyl group which may be substituted with a halogen atom include a 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 methylsulfonyl group, an ethanesulfonyl group, and a trifluoromethylsulfonyl 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 C 1 .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, 2, 2, 2—Trifluoroec Group, pentafluoroethyl group, propyl group, 3, 3, 3-trifluoropropyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group and 4, 4, 4 One 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 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-trifluoro group, pentafluoroethyl 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 which may be 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 can form 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, vinegar Examples thereof include salts with acid, propionic acid, succinic acid, succinic acid, benzoic acid, p-toluenesulfonic acid, methanesulfonic 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-jetoxetane, halogenated hydrocarbons such as chloroform, benzene, dichlorobenzene, acetate Nitriles such as nitrile, aprotic polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, 1-methyl-2-pyrrolidone, 1,3-dimethylimidazolinone, dimethylsulfoxide, water and the like A mixture may be mentioned.
  • ketones such as acetone and methyl ethyl ketone
  • 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 15 Ot :, and the reaction time is usually in the range of 0.1 to 100 hours.
  • 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.
  • post-treatment operations such as drying and concentration of the organic layer.
  • the isolated compound represented by the formula (I-11) can be further purified by recrystallization, column chromatography or the like.
  • R 1 — 1 is a C 1 C 6 alkyl group optionally substituted with a halogen atom, substituted with a halogen atom C 2—C 6 alkenyl group, C 2—C 6 alkynyl group, C6—C 14 aryl group, C7—C 11 aralkyl group, C 2—C 6 alkoxyalkyl group, C 7— C14 aryloxyalkyl group, C3-C6N, N-di (alkyl) aminoalkyl group, C2-C6 alkylthioalkyl group, C2-C6 alkylsulfurylalkyl group, C2-C6 alkyl Represents a sulfonylalkyl group or a C 3 -C 9 alkoxyalkoxyalkyl group; ]
  • 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-dimethoxyethane, ethers such as 1,2-diethoxyethane, etc., halogenated hydrocarbons such as chloroform, benzene and dichlorobenzene, nitriles such as acetonitrile, Aprotic polar solvents such as N, 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 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 organic lithium such as normal butyl lithium and lithium diisopropylamide and triethylamine, pyridine, 1,8-diazabicyclo [5,4,0] undecene (hereinafter abbreviated as DBU).
  • 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 concentrating the organic layer, whereby a compound represented by the formula (I-12) is obtained.
  • a compound represented by the formula (I-12) is obtained.
  • the isolated compound represented by the formula (1-2) can be further purified by recrystallization, column chromatography or the like.
  • R 1 - 2 are halogen atoms which may be substituted with child C 1 one C 6 alkyl group, it may be substituted with a halogen atom C.2—C 6 alkenyl group, C 2—C 6 alkynyl group, C7—C 11 aralkyl group, C 2—C 6 alkoxyalkyl group, C 7—C 14 aralkyl group, C3— C6N, N-di (alkyl) aminoalkyl group, C2-C6 alkylthioalkyl group, C2-C6 alkylsulfinylalkyl group, C2-C6 alkylsulfonylalkyl group, C3-C9 alkoxyalkoxyalkyl group C 2—C 6 alkoxycarbonyl group, C 8—C 12 aralkyloxycarbonyl group, N, N—di (CI—C6 alkyl) group, rub
  • 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 ethoxysulfonyloxy 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 4-1 ethers, ethers such as 1,2-dimethoxyethane, 1,2-diethoxyethane, halogenated hydrocarbons such as chloroform, chlorobenzene, dichlorobenzene, nitriles such as acetonitrile, NN-dimethylformamide , N, N-dimethyla Examples thereof include aprotic polar solvents such as cetamide, 1-methyl-2-pyrrolidone, 1,3-dimethylimidazolinone and dimethyl sulfoxide, water, and mixtures thereof.
  • ketones such as acetone and methyl ethyl ketone
  • 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.
  • Metal or alkali earth metal hydride, alkali metal such as sodium carbonate or potassium carbonate or carbonate of alkaline earth metal, sodium metallate, alkali metal alcoholate such as sodium methylate
  • Examples include 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 using a reagent that is liquid under the reaction conditions, but is usually based on 1 mole of the compound represented by the formula (I 1 1).
  • the compound represented by the formula (V) is 1 to 4 mol, and the base is 1 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 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 (1-3) is obtained.
  • Product can be isolated.
  • the isolated compound represented by the formula (1-3) can be further purified by recrystallization, column chromatography or the like.
  • L 2 represents a halogen atom (for example, a chlorine atom, a bromine atom and an iodine atom). ]
  • the reaction is usually performed in a solvent in the presence of a base.
  • Solvents used in the reaction include, for example, ketones such as acetone and methyl edyl 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 acetonitrile, N , N-dimethylformamide, N, N-dimethylacetamide, 1-methyl-2-pyrrolidone, 1,3-dimethylimidazolinone, dimethylsulfoxide, and other aprotic polar solvents, water, and mixtures thereof.
  • ketones such as acetone and methyl edyl 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 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, diisopropylethylamine, pyridine and DBU.
  • the amount of the reagent used in the reaction may be an excess of each when a reagent that is liquid under the reaction conditions is used, but usually the compound 1 represented by the formula (VI I)
  • 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) can be isolated.
  • the isolated compound represented by the formula (1-2) 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.
  • 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, dichlorobenzene, nitriles such as acetonitrile, N, N
  • Examples include aprotic polar solvents such as —dimethylformamide, N, N-dimethylacetamide, 1-methyl-2-pyrrolidone, 1,3-dimethylimidazolinone, dimethylsulfoxide, water, and mixtures thereof.
  • 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 Examples include alkaline earth metal carbonates, alkali metal alcoholates such as sodium edilate 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 trimethyl silane and triethyl silane.
  • chlorocarbonylating agent used in the reaction examples include phosgene, trimethyl oral formate, bis (trichloromethyl) carbonate and the like.
  • the amount of the reagent used in the reaction is usually 1 to 4 moles of the trialkylchlorosilane compound and 1 to 4 moles of the carbonyl carbonylating agent with respect to 1 mole of the compound represented by the formula (VI II).
  • the base is usually in a ratio of 1 to 4 moles.
  • 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 (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 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, 1,2-diethoxyethane, halogenated hydrocarbons such as chloroform, chlorobenzene, dichlorobenzene, nitrile such as acetonitrile, N, N-dimethylformamide, Aprotic polar solvents such as N, N-dimethylacetamide, 1-methyl-2-pyrrolidone, 1,3-dimethylimidazolinone, dimethyl sulfoxide, water, and mixtures thereof.
  • ketones such as acetone and methyl ethyl ketone
  • aromatic hydrocarbons such as
  • 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.
  • Examples include organic lithium such as alcoholate, normal butyl lithium, 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 150 ° C, and the reaction time is usually in the range of 0.1 to 200 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, hexane, aliphatic hydrocarbons such as' heptane, jetyl ether, Ethers such as lahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane, 1,2-jetoxetane, Halogenated hydrocarbons such as roloform, black benzene, dichlorobenzene, nitriles such as acetonitrile, ⁇ , N-dimethylformamide, N, N-dimethylacetamide, 1-methyl-2-pyrrolidone, 1,3-dimethylimidazo
  • Examples include aprotic polar solvents such as linone and dimethyl sulfoxide, water, and mixtures thereof.
  • 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 alkaline earth metal carbonate, sodium ethylate, sodium methylate
  • Examples include organic lithium such as alcoholate, normal butyl lithium, lithium diisopropylamide, and organic bases such as triethylamine, pyridine, and DBU.
  • 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).
  • Skin reaction temperature is usually in the range of ⁇ 78 to 150 ° C.
  • 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 can be obtained by a method known per se, for example, alkylation, alkenylation, alkynylation, acylation, amination, sulfidation, sulfielation, sulfonation, oxidation, reduction. Substituents can be converted to other desired substituents by halogenation, nitration and the like. As an aspect of this compound, the following are mentioned, for example in this compound. m is 0 or 1 ( ⁇ '— ethyl) benzoylurea compound;
  • X and ⁇ are both fluorine atoms ( ⁇ , ethyl) benzoylurea compounds; X and ⁇ are both chlorine atoms ( ⁇ , ethyl) benzoylurea compounds; X is a fluorine atom and ⁇ is a chlorine atom Yes ( ⁇ , ⁇ tyl) benzoylurea compound;
  • R 1 is a hydrogen atom ( ⁇ '—ethyl) benzoylurea compound
  • R 3 is a C 1 -C 4 alkoxy group optionally substituted with a halogen atom, a halogen atom or a C 1 C 4 alkyl group optionally substituted with a halogen atom ( ⁇ , ethyl) benzoylurea compound ;
  • R 3 is a halogen atom, a C 1 mono C 4 alkoxy group which may be substituted with a halogen atom, or a C 1 mono C 4 alkyl group which may be substituted with a halogen atom, and m is 0 or 1 ( N, -ethyl) benzoylurea compound;
  • R 1 is a hydrogen atom
  • R 3 is a halogen atom, which may be substituted with a halogen atom, or 1 C 4 alkoxy group or a C 1 -C 4 alkyl group which may be substituted with a halogen atom, (N, -ethyl) 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 inactive body include a solid carrier, a liquid carrier, and an ointment base.
  • the plant protection agent of the present invention is usually formulated with an emulsifier, suspending agent, spreading agent, penetrating agent, wetting agent, mucilage agent, stabilizer, etc., if necessary, and formulated into an appropriate form. Yes.
  • examples of such formulations include emulsions, liquids, microemulsions, emulsions, flowables, oils, wettable powders, aqueous solvents, sols, powders, granules, fine granules, microcapsules, tablets , Ointments, capsules, pellets, poisonous baits, sprays, aerosols, coating agents, etc.
  • the compound or a salt thereof is usually 0.1 to 80% by weight, preferably 1 About 80% by weight is contained.
  • 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 0.1 to 80% by weight, preferably 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 0.1 to 50% by weight, preferably about 0.1 to 20% by weight.
  • solid carriers examples include vegetable powder (soybean powder, tobacco powder, wheat flour, wood powder, etc.), mineral powder (kaolin, bentonite, acid clay, talc such as talc powder, ore stone powder, etc. And silicas such as diatomaceous earth and mica powder), alumina, sulfur powder, activated carbon, calcium carbonate, ammonium sulfate, sodium bicarbonate, lactose, urea and the like.
  • vegetable powder sibean powder, tobacco powder, wheat flour, wood powder, etc.
  • mineral powder kaolin, bentonite, acid clay, talc such as talc powder, ore stone powder, etc.
  • silicas such as diatomaceous earth and mica powder
  • alumina sulfur powder
  • activated carbon calcium carbonate
  • ammonium sulfate sodium bicarbonate
  • lactose lactose
  • urea urea and the like.
  • liquid carrier examples include water, alcohols (methyl alcohol, ethyl alcohol, ⁇ -propyl alcohol, isopropyl alcohol, ethylene glycol, etc.), ketones (acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexane).
  • alcohols methyl alcohol, ethyl alcohol, ⁇ -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 such as kerosene, fuel oil, machine oil
  • aromatic hydrocarbons Toluene, xylene, solvent naphtha, methyl naphthalene, etc.
  • halogenated hydrocarbons diichloromethane, black mouth form, tetrachlorocarbon, etc.
  • acid amides ⁇ , ⁇ -dimethylformamide, ⁇ , ⁇ Jimechirua acetamide, Nyu- such methylpyrrolidone
  • esters acetate Echiru acetate heptyl, fatty acid glycerol esters, ⁇ chromatography Petit-butyrolactone etc.
  • nitriles such ( ⁇ Se Tonitoriru, such as propionic nitrile) and the like.
  • liquid carrier When a liquid carrier is used for the plant protection agent of the present invention, 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), cellulose 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.
  • an ointment base is used for the plant protection agent of the present invention
  • one or more of these soft growth 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.
  • the surfactant used in such a case include stalagmites and polyoxins.
  • Siethylene alkyl aryl ethers e.g., Neugen (trade name) 1-4 2 (EA 1 4 2 (trade name)); manufactured by Daiichi Kogyo Seiyaku Co., Ltd. (non-trade name); Manufactured by Kao Corporation
  • alkyl sulfates e.g.
  • Emeral 10 (trade name), emal 40 (trade name); Kao Corporation], alkyl benzene 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), Nonipol 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.
  • Acaricides, machine oils, nematicides, herbicides, plant hormones, plant growth regulators, fungicides (eg copper fungicides, organochlorine fungicides, organic sulfur fungicides, phenolic fungicides Agent), synergist, attractant, repellent, safener, pigment, fertilizer, etc. may be appropriately blended.
  • Such other insecticides include, for example,
  • Car tap bensul tap, thiocyclam monosultap, bisultap, etc .;
  • Aldrin dieldrin, dienochlor, endosulfan, methoxychlor, etc .
  • Avermectin-B cyenopyrafen, bromopropylate, buprofezin, chlorphenapyr, chlorphenapyr, cyenopyrafen, cyromazine, ene (1, 3- Dichloroprop) , Emamectin-benzoate, fenazaquin, frepyrazo, flupyrazofos hydroprene, indoxacarb, indoxacarb, lepimectin, metoxadiazone, milbedia Mycin A (milbemycin-A), pymetrozine, pyridalyl, pyriproxyfen, spinosad, sulfluramid, tolfenpyrad, triazamate, Flubendiamide, cyilumetofen arsenic acid, benguchiiaz, lime nitrogen (Calciumcyanamide), lime sulfur compound (Calcium polysulf ide), chlordane, DDT, D
  • R 1 is Me, C 1, Br or F
  • R 2 is F, Cl, Br, CI—C 4 haloalkyl, or C 1—C 4 haloalkoxy
  • R 3 is F, C 1 or Br
  • R 4 is H, one or more halogen atoms; CN; SMe; S (O) Me; S (0) 2 Me and C 1 -C 4 alkyl optionally substituted with OMe, C 3-
  • 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, Acequinocyl, amitraz, benzoximate, bromopropylate, chinomethionat, chlorobenzilate, CP CB S (chlorfenson), chlorofuente Gin (clofentezine), Kelsen (dicofol), etoxazole, fenbutatin oxide, fenothiocarb, fenpyroximate, fluacrypyrim, fluproxyfen, fluproxyfen Hexythiazox, propargite (BPPS), polynactins, pyridaben, pyrimidifen, tebufenpyrad, tetradifon, spirodiclofen, spirodiclofen Helmet (amidof lumet).
  • the active ingredient of the nematocide include, for example,
  • DC IP fosthiazate, levamisol hydrochloride, methyisothiocyanate, morantel tartarate, imicyafos, etc.
  • active ingredients of fungicides For example, acibenzolar-S-methyl, ambam, amisulbrom, ampropylfos, anilazine, azoxystrobin, benalaxyl, benalaxyl Nodanil, benomyl, benthiaval icarb, benthiazole, bethoxazin, bitertanol, blasticidin—S (blasticidin-S), pordo 1 Liquid (Bordeaux mixture), Poscalid (boscalid), Bromuconazole Buthiobate, calcium hypochlorite, calcium polysulfide, captan, carbendazol, carboxin, carpropamid, clobbenthiazone , Chloroneb, chloropicrin, chlorothalon
  • the active ingredients of synergists include, for example, piperonyl butoxide, sesamex, sulfoxide, N— (2-ethylhexyl) 1, 8, 9, 10-trinorpolone 1 5
  • Examples of active ingredients in safeners include: -EN-2,3-dicarboximide (MGK 264), WARF-anti-resistant (WARF-anUresistant), and dithy lmaleate.
  • Benoxacor cloquintocet-mexyl, ciometrinil, daimuron, dichlormid, fenchlorazole-ethyl, Fenclorim, flurazole (urazole), fluluximen (f luxofenim), furilol (furi l azole), mefenpyr-diethyl, G19 nap thal ic anhydride, oxa betrinyl ( oxabetrini l).
  • 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, and the carrier '(liquid carrier, solid carrier) The ointment base material) 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.
  • Examples include hydroponic liquids at Matsuto and hydroponic farms.
  • Specific methods for directly applying to roots or seeds include, for example, spraying the plant protection agent of the present invention to roots or seeds, coating, dipping, impregnation, coating, film coating, and pellets. Examples of the coating method include:
  • the plant preservation of the present invention is used.
  • a method of applying to the rhizosphere of a plant in the case of a hydroponic solution, the plant preservation of the present invention is used.
  • a method of mixing a hydroponic liquid or mixing a hydroponic liquid there is a method of mixing a hydroponic liquid or mixing a hydroponic liquid.
  • planting hole treatment planting hole spraying, planting hole soil mixing
  • plant source treatment stock source spraying, plant source soil mixing, plant source irrigation, late seedling season, plant source treatment
  • Grooving treatment spreading grooving, mixing grooving soil
  • cropping treatment spreading, sprinkling soil, mixing with soil, sprinkling during growing season
  • sprinkling treatment at sowing spreading sprinkling at sowing, sowing
  • Tokusaku soil mixing full treatment
  • other spraying treatments growth foliar spraying, spraying under canopy or around trunk, soil surface spraying, soil surface blending, sowing hole spraying, buttocks Surface spraying, inter-strain spraying
  • other irrigation treatments irrigation, seedling irrigation, chemical injection, local irrigation, chemical drip irrigation, chemi-gation
  • nursery box treatment noursing box spraying, seedling box irrigation
  • Seedling tray treatment soil irrigation, seedling irrigation, chemical injection, local irrigation, chemical drip irrigation,
  • 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,
  • This compound or a salt thereof per hectare is usually about 0.3 to 300 g, preferably about 50 to 300 g, and is applied directly to the root of the plant or palm.
  • the present compound or a salt thereof is usually from 0.001 to 0.lg, preferably from 0.05 to 0.02 per plant plant or one seed of plant. The ratio is about g.
  • 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. Examples include the growth stage in the field.
  • 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 plant root has developed, and applying the present compound or a salt thereof to the soil or the like in advance. And a method for developing plant roots in the soil.
  • 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, watermelons, melons, etc.
  • Cabbage mustard, broccoli, cauliflower, etc.
  • asteraceae vegetables burdock, cypress, artichoke yoke, lettuce, etc.
  • liliaceae vegetables laeek, onion, garlic, asparagus, etc.
  • celery vegetables carrot, parsley) , Celery, American Bow Fu, etc.
  • Zhazaceae Vegetables Haourenso, Fudansou, etc.
  • Lamiaceae Vegetables Pig, Mint, Basil, etc.
  • Strawberry Sweet Potato, Yamanimo, Satoimo, etc .
  • Berries (apples, pears, two pears, quince, quince mouth, etc.), berries (peaches, plums, nectarines, ume, sweet potato, apricot, brune etc.), citrus fruits (citrus mandarin orange, orange, lemon, lime, Grapefruit, etc.), nuts (cris, walnuts, hazelnuts, almonds, bisyucho, cashew nuts, macadamia nuts, etc.), berries (bull berries, cranberries, blackberries, raspberries, etc.), grapes, oysters, ori Ibu, bean paste, banana, coffee, date palm, coconut palm, etc .;
  • Lawn grass such as Noshipa, Koraishiba, Bermudagrass, Bentgrass, Ryegrass, Bullgrass, Fescue; Pastures such as ryegrass, orchardgrass, fescue, bluegrass, clover, and alfa alpha.
  • HPPD inhibitors such as Isoxaflutol
  • ALS inhibitors such as Imagase pills and Thifensulfuron methyl
  • EPSP synthase inhibitors such as Imagase pills and Thifensulfuron methyl
  • EPSP synthase inhibitors Daryumin synthase inhibitors
  • the use of acetyl CoA carboxyxylase inhibitors; or herbicides such as promoxinil does not cause phytotoxicity problems.
  • Clearf ie ld® canola with tolerance to imidazolinone herbicides
  • STS soybeans with tolerance to sulfonylurea herbicides
  • SR corn that has been given resistance to acetyl acetylase inhibitors.
  • Crop resistance imparted against Asechiru CoA carboxylase inhibitor can be, for example p r oc. Nat l. Acad . Sc i. Is described in USA 1990, 87, 7175 or the like.
  • acetyl CoA force lpoxylase that expresses resistance to a acetyl CoA carboxylase inhibitor is known, for example, in Weed Science 53: 728-746, 2005.
  • a gene that codes for this mutant type of acetyl CoA carboxylase is introduced by genetic recombination technology, or a gene that codes for acetyl CoA carboxylase is introduced with a mutation related to conferring resistance to acetyl CoA carboxylase.
  • the crop can be conferred with acetyl-CoA-powered lpoxylase-inhibiting herbicide tolerance.
  • crops maize varieties that have been given tolerance to glyphosate and dalfosine 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 from Bacillus cereus and Bacillus popilie; 6-endotoxins such as CrylAb, CrylAc, CrylF, CrylFa2, Cry2Ab, Cry3A, Cry3Bbl or Cry9C from Bacillus thuringiensis, Insecticidal proteins such as VIPK VIP2, VIP3 or VIP3A; insecticidal proteins derived from nematodes; toxins produced by animals such as scorpion toxins, spider toxins, bee toxins or insect-specific neurotoxins; filamentous fungal toxins; plant lectins; Protease inhibitors such as trypsin inhibitor, serine protease inhibitor, patatin, cis-actin and papain inhibitor; Ribosome inactivating protein (RIP) such as lysine, maize-RIP, abrin, saporin, briodin; 3.—Hydroxysteroid oxidase, ecdysteroid
  • Insecticidal toxins also include eight-ib protein of the insecticidal protein and a protein in which a part of the amino acids constituting the 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.
  • “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.
  • “crop products” that have been given the ability to produce insecticidal toxins through genetic recombination technology, for example, Yi eldGard® (a corn variety that expresses CrylAb toxin), YieldGard Rootworm® (Cry3Bbl Maize varieties that express toxins), YieldGard Plus® (a corn variety that expresses CrylAb and Cry3Bbl toxins), Herculex I® (phosphinothricin N-acetyltransferase to confer resistance to CrylFa2 toxin and gallofine) (PAT) -expressing corn varieties), UCOTN33B® (CrylAc toxin-expressing evening varieties), Bol lgard I® (CrylAc toxin-expressing evening varieties), Bol lgard II® (CrylAc and Cry2
  • Antipathogenic substances produced by microorganisms include, for example, PR Yunpaku (PRPs, described in EP-A-0392 225); sodium channel inhibitors, calcium channel inhibitors (virus produced KP1, ⁇ 4, ⁇ 6 toxins, etc.) Ion channel inhibitors; stilbene synthase; bibenzyl synthase; chitinase; glucanase;. PR protein; peptide antibiotics, antibiotics with heterocycles; and proteins involved in plant disease resistance ( W0 03/000906)).
  • PR Yunpaku PRPs, described in EP-A-0392 225
  • sodium channel inhibitors calcium channel inhibitors (virus produced KP1, ⁇ 4, ⁇ 6 toxins, etc.) Ion channel inhibitors
  • stilbene synthase bibenzyl synthase
  • chitinase glucanase
  • PR protein peptide antibiotics, antibiotics with heterocycles
  • proteins involved in plant disease resistance W0 03/000906
  • Examples of crops that have been given the ability to produce anti-pathogenic substances by genetic engineering techniques are those described in EP-A-0 392 225, W095 / 33818, and EP-A-0 353 191, for example. Can be mentioned.
  • the plant protection method of the present invention can protect plants from harm by pests that cause harm such as feeding or sucking (for example, harmful arthropods such as insects and harmful mites). Specific examples of are as follows.
  • Hemiptera pests Laodelphax striatellus, Nilaparvata lugens, Sungats such as Sogatella furcifera, Nephotettix cincticeps, Nephotettix s gossypii), peach aphid (Myzus persicae), radish aphid (Brevicoryne brassicae, churisritsu aphid) (Macrosiphum euphorbiae), potato aphid (Aulacorthum solani), wheat Aphids such as (Toxoptera citricidus), Nezaraantenna, Riptortus clavetus, Leptocorisa chinensis, Eysarcoris parvus, misalta Stink bugs such as Nisshudo plant bug (Lygus lineolaris), on Sit whitefly (Trialeurodes vaporariorum), whiteflies such as bemisi
  • Ticks such as (Cheyletus moorei).
  • N-ethyl-1-fluoro-4- (1, 1, 2, 2-tetrafluoroethoxy) aniline 0.51 g in a solution of 2.0 ml of jetyl ether in a solution of 2,6-difluorobenzo
  • a solution prepared by dissolving 0.36 g of ylisocyanate in 0.5 ml of jetyl ether was added under ice cooling, and the mixture was stirred at room temperature for 2 hours. Hexane 5m 1 is added to the reaction mixture, followed by filtration.
  • N-Ethyl-2-Fluoro-4 (1, 1, 2, 2-Tetrafluoroethoxy) aniline 0.5- 2
  • 2-chloro 6-full A solution prepared by dissolving 0.39 g of o-benzoyl isocyanate in 0.5 ml of jetyl ether was added under ice-cooling, and the mixture was stirred at room temperature for 2 hours.
  • N-Ethyl-2-fluoro-4- (1,1,2,2-Tetrafluoroethoxy) aniline 0.51 g in a solution of 2.0 ml of jetyl ether in a solution of 2,6-dichlorobenzo
  • a solution prepared by dissolving 0.42 g of ylisocyanate in 0.5 ml of jetyl ether was added under ice cooling, and the mixture was stirred at room temperature for 2 hours.
  • N-Ethyl-2-fluoro-4- (trifluoromethyl) aniline 0.51 g in jetyl ether 2.
  • OmU dissolved solution, 2,6-difluorobenzoyl isocyanate 0.44 g in jetyl ether The solution dissolved in 0.5 ml was added under ice-cooling and stirred at room temperature for 2 hours.
  • a part represents a weight part.
  • This compound (1), (2), (4), (5), (7), (8), (9), (10) (11), (13), (14), (16) and ( 17) 5mg each of Sorgen TW-20 (Daiichi Kogyo Seiyaku Co., Ltd.) and acetone mixed solution (mixing volume ratio; Sorgen TW-20: Acetone 1: 19) dissolved in 0.1ml, 3m 1 with ion-exchanged water
  • a test chemical solution for the test compound was prepared by diluting the test compound. Cabbage seedlings were grown in a seedling container (capacity: 27 ml, height: 5. O cm) to 2.5 leaf stage. The whole amount of the test solution was irrigated on the surface of the cabbage seedling.
  • This compound (4), (5), (7), (8), (10), (11), (16) and (17) 5 mg each of Sorgen TW-20 (Daiichi Kogyo Seiyaku) Mixed solution (mixed volume ratio; Sorgen TW-20: Acetone 1: 19) Dissolved in 0.1 ml, diluted to 3 ml with ion-exchanged water, prepared a test drug solution for the test compound.
  • a seedling container (capacity: 27 ml, height: 5.0 cm) was filled with soil and sown with cabbage. The whole amount of the test chemical was irrigated on the soil surface. The cabbage was raised until 28 days after the treatment.

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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 sel dudit composé, 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/JP2007/057696 2006-04-03 2007-03-30 Procédé servant à protéger un plante WO2007116948A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015016251A1 (fr) * 2013-07-31 2015-02-05 バイエルクロップサイエンス株式会社 Composition agrochimique pour la culture par semis direct de riz paddy, et son procédé d'utilisation

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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

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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

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015016251A1 (fr) * 2013-07-31 2015-02-05 バイエルクロップサイエンス株式会社 Composition agrochimique pour la culture par semis direct de riz paddy, et son procédé d'utilisation
JP2015030678A (ja) * 2013-07-31 2015-02-16 バイエルクロップサイエンス株式会社 水稲の直播栽培用農薬組成物とその使用方法。

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