WO2012077221A1 - Dérivé de 3-aminooxalylaminobenzamide et agent insecticide et acaricide l'incluant en tant que principe actif - Google Patents

Dérivé de 3-aminooxalylaminobenzamide et agent insecticide et acaricide l'incluant en tant que principe actif Download PDF

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WO2012077221A1
WO2012077221A1 PCT/JP2010/072197 JP2010072197W WO2012077221A1 WO 2012077221 A1 WO2012077221 A1 WO 2012077221A1 JP 2010072197 W JP2010072197 W JP 2010072197W WO 2012077221 A1 WO2012077221 A1 WO 2012077221A1
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秀一 薄井
誠司 柿沼
福地　俊樹
祐子 木下
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アグロカネショウ株式会社
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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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/46—N-acyl derivatives
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/30—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the groups —CO—N< and, both being directly attached by their carbon atoms to the same carbon skeleton, e.g. H2N—NH—CO—C6H4—COOCH3; Thio-analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/56—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having carbon atoms of carboxamide groups bound to carbon atoms of carboxyl groups, e.g. oxamides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/88—Carboxylic acid amides having nitrogen atoms of carboxamide groups bound to an acyclic carbon atom and to a carbon atom of a six-membered aromatic ring wherein at least one ortho-hydrogen atom has been replaced
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
    • C07C237/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated

Definitions

  • the present invention relates to novel 3-aminooxalylaminobenzamide derivatives and insecticides and acaricides containing these as active ingredients.
  • Patent Document 1 Although a compound having a fluorine atom at the 6-position is disclosed as Y in the phenyl group of the benzamide moiety, a 3-aminooxalylaminobenzamide derivative having a halogen atom introduced at the 2-position is disclosed. It is not specifically disclosed.
  • the present applicant has further improved by introducing a halogen atom at the 2-position of the phenyl group of the benzamide moiety of the 3-aminooxalylaminobenzamide derivative.
  • the present inventors have found a compound having an insecticidal and acaricidal action and have arrived at the present invention.
  • An object of the present invention is to provide a specific 3-aminooxalylaminobenzamide derivative that exhibits higher effects against various pests and mites.
  • the present inventors have introduced a 3-aminooxalylaminobenzamide derivative represented by the following formula (hereinafter referred to as “the compound of the present invention”) into which a halogen atom has been introduced into the phenyl group of the benzamide moiety. ”)” was found to be a useful compound having an excellent insecticidal and acaricidal action, and the present invention was completed.
  • the present invention provides the following formula [1], [1] (Wherein R 1 and R 2 each independently represent a hydrogen atom, a C 1 -C 3 alkoxy group, a C 1 -C 3 haloalkoxy group, a halogen atom, or a C 1 -C 5 alkyl group).
  • R 3 and R 4 are each independently a hydrogen atom, a C 1 -C 8 alkyl group, a C 1 -C 8 haloalkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 haloalkenyl group, a C 2- C 6 alkynyl group, C 3 -C 8 cycloalkyl group or C 3 -C 8 halocycloalkyl group, provided that R 3 and R 4 are bonded to each other to form a C 3 -C 8 alkylene bond.
  • the C 3 -C 8 alkylene bond may be substituted with a halogen atom or a C 1 -C 5 alkyl group.
  • R 5 represents a C 1 -C 5 haloalkyl group.
  • R 6 and R 7 are each independently a hydrogen atom, C 1 -C 5 alkyl group, C 3 -C 8 cycloalkyl group, C 1 -C 5 haloalkyl group, C 1 -C 3 alkoxy C 1 -C 4 Alkyl group, C 2 -C 6 alkenyl group, C 2 -C 6 haloalkenyl group, C 1 -C 4 alkylcarbonyl group, C 1 -C 4 haloalkylcarbonyl group, C 1 -C 4 alkylsulfonyl group, C 1- A C 4 haloalkylsulfonyl group, a C 1 -C 3 alkoxycarbonyl group or a C 1 -C 3 haloalkoxycarbonyl group;
  • X represents a halogen atom.
  • Y is independently a hydrogen atom, halogen atom, hydroxyl group, nitro group, cyano group, C 1 -C 5 alkyl group, C 1 -C 5 haloalkyl group, C 1 -C 3 alkylamino group, di-C 1 ⁇ C 3 alkyl amino group, C 1 ⁇ C 3 an alkoxy group or a C 1 ⁇ C 3 haloalkoxy group
  • Z is independently hydrogen atom, halogen atom, hydroxyl group, nitro group, cyano group, C 1 -C 5 alkyl group, C 1 -C 5 haloalkyl group, C 1 -C 3 alkoxy group or C 1 -C 3 A haloalkoxy group; n represents an integer of 0 to 3, and m represents an integer of 0 to 2.
  • an insecticide and acaricide hereinafter, also simply referred to as “the insecticide and acaricide of the present invention” containing the derivative as an active ingredient.
  • the compound of the present invention exhibits an excellent effect on pests and mites.
  • R 1 and R 2 each independently represent a hydrogen atom, a C 1 -C 3 alkoxy group, a C 1 -C 3 haloalkoxy group, a halogen atom, or a C 1 -C 5 alkyl group.
  • the alkyl group in these groups may be branched or linear.
  • a group having a C 1 -C 3 alkyl group a methyl group, an ethyl group, an n-propyl group, an isopropyl group, and the like are preferable.
  • Preferred examples include a group, 3-pentyl group, neopentyl group, t-pentyl group and the like.
  • C 1 -C 3 alkoxy group examples include methoxy group, ethoxy group, n-propyloxy group, isopropyloxy group and the like.
  • C 1 -C 3 haloalkoxy groups include, for example, difluoromethoxy groups, trifluoromethoxy groups, pentafluoroethoxy groups, 1,1,2,2-tetrafluoroethoxy groups, 2,2,2-trifluoroethoxy groups.
  • Heptafluoro-n-propyloxy group, heptafluoro-i-propyloxy group, 1,1,2,3,3,3-hexafluoro-n-propyloxy group and the like can be preferably listed.
  • Preferred examples of the halogen group include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • R 1 is preferably, for example, a methyl group, an ethyl group, a trifluoromethoxy group, or a methoxy group.
  • R 2 is preferably a methyl group, an ethyl group, a chlorine atom, a bromine atom, or an iodine atom.
  • R 3 and R 4 each independently represents a hydrogen atom, a C 1 -C 8 alkyl group, a C 1 -C 8 haloalkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 haloalkenyl group, C 2 A C 6 alkynyl group, a C 3 -C 8 cycloalkyl group or a C 3 -C 8 halocycloalkyl group;
  • the C 1 -C 8 alkyl group is a linear or branched alkyl group such as a methyl group, ethyl group, n-propyl group, isopropyl group, n- Butyl group, isobutyl group, s-butyl group, t-butyl group, n-pentyl group, isopentyl group, 2-pentyl group, 3-pentyl group, neopentyl group, t-pentyl group, n-hexyl group, t- An octyl group, an n-octyl group and the like can be preferably listed.
  • the C 1 -C 8 alkyl group is preferably a C 1 -C 6 alkyl group.
  • the C 1 -C 6 alkyl group is a linear or branched alkyl group such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, Preferred examples include isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, 2-pentyl, 3-pentyl, neopentyl, t-pentyl, and n-hexyl. be able to.
  • C 1 -C 8 alkyl groups are C 1 -C 4 alkyl groups such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, and s-butyl group.
  • T-butyl group and the like can be preferably listed.
  • the number of halogen atoms is arbitrary, and may be 1 to several, for example, 1 to 17 depending on the number of carbon atoms of the alkyl group.
  • the C 1 -C 8 haloalkyl group is a linear or branched haloalkyl group such as a monofluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a monochloromethyl group, a dichloromethyl group.
  • the C 1 -C 8 haloalkyl group is a linear or branched haloalkyl group such as a monofluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a monochloromethyl group, a dichloromethyl group.
  • C 1 -C 6 haloalkyl groups are C 1 -C 4 haloalkyl groups, which are linear or branched haloalkyl groups, such as monofluoromethyl groups, difluoromethyl groups, Fluoromethyl group, monochloromethyl group, dichloromethyl group, trichloromethyl group, monobromomethyl group, dibromomethyl group, tribromomethyl group, 1-fluoroethyl group, 2-fluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 2-chloro-2,2-difluoroethyl group, 1-chloroethyl group, 2-chloroethyl group, 2,2-dichloroethyl group, 2,2,2-trichloroethyl group 1-bromoethyl group, 2-bromoethyl group, 2,2-dibromoethyl group, 2,2,2-trib
  • C 1 -C 5 haloalkyl groups are C 3 -C 4 haloalkyl groups, which are linear or branched haloalkyl groups such as 1,3-difluoro-2-propyl group, 3,3-difluoropropyl group, 3,3,3-trifluoropropyl group, 3,3,3-trichloropropyl group, 1,3-dichloro-2-propyl group, 1,1,1-trifluoro- 2-propyl group, 1-chloro-3-fluoro-2-propyl group, 1,1,1,3,3,3-hexafluoro-2-propyl group, 1,1,1,3,3,3- Hexafluoro-2-chloro-2-propyl group, 2-bromo-1,1,1,3,3,3-hexafluoro-2-propyl group, 2,2,3,3,3-pentafluoropropyl group , Heptafluoroisopropyl group, heptafluoro -N
  • C 2 -C 6 alkenyl groups are straight chain or branched alkenyl groups such as vinyl, allyl, 1-methyl-2-propenyl, 2- A methyl-2-propenyl group, 2-butenyl group, 3-butenyl group and the like can be preferably listed.
  • Preferred C 2 -C 6 alkenyl groups are C 3 -C 4 alkenyl groups, which may be linear or branched, such as allyl groups, 1-methyl-2- Propenyl group, 2-methyl-2-propenyl group, 2-butenyl group, 3-butenyl group and the like can be preferably listed.
  • the C 2 -C 6 haloalkenyl group is a haloalkenyl group which may be linear or branched, such as a 2-chloro-2-propenyl group or a 3-chloro-2-propenyl group.
  • C 2 -C 6 haloalkenyl groups are C 3 -C 4 haloalkenyl groups, which may be linear or branched, such as 2-chloro-2-propenyl.
  • the C 2 -C 6 alkynyl group is a linear or branched alkynyl group, such as a propargyl group, a 1-methylpropargyl group, a 2-butyne group, a 3-butyne group, etc. Can be preferably listed.
  • the C 3 to C 8 cycloalkyl group may be branched, for example, a cyclopropyl group, a 1-methylcyclopropyl group, a 2-methylcyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group. Groups and the like can be preferably listed. Preferable examples of the C 3 -C 8 cycloalkyl group include C 3 -C 6 cycloalkyl groups.
  • C 3 -C 8 cycloalkyl groups are C 3 -C 5 cycloalkyl groups, which may be branched, for example, cyclopropyl groups, 1-methylcyclopropyl groups, 2-methylcyclohexanes.
  • Propyl group, cyclobutyl group, cyclopentyl group and the like can be preferably listed.
  • the C 3 -C 8 halocycloalkyl group is an optionally branched halocycloalkyl group such as a 2-fluorocyclopropyl group, a 2,2-difluorocyclopropyl group, 2,2, A 3,3-tetrafluorocyclobutyl group, a 3,3-difluorocyclobutyl group, a 2-chlorocyclohexyl group, a 4-chlorocyclohexyl group, and the like can be preferably listed.
  • R 3 and R 4 may be bonded to each other to form a C 3 -C 8 alkylene bond.
  • Examples of the C 3 -C 8 alkylene bond include (CH 2 ) 3 and (CH 2 ) 4 , (CH 2 ) 5 , (CH 2 ) 6 and the like can be preferably listed.
  • Preferred examples of the C 3 to C 8 alkylene bond include C 3 to C 6 alkylene bonds.
  • the C 3 to C 8 alkylene bond may be substituted with a halogen atom as defined above or a C 1 to C 5 alkyl group.
  • R 3 is preferably a methyl group or an ethyl group.
  • R 4 includes methyl, ethyl, n-propyl, isopropyl, cyclopropyl, t-butyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-tri A fluoroethyl group is preferred.
  • R 5 represents a C 1 -C 5 haloalkyl group.
  • the C 1 -C 5 haloalkyl group is a linear or branched haloalkyl group such as a monofluoromethyl group, a difluoromethyl group, a trifluoromethyl group, or a monochloromethyl group.
  • R 6 and R 7 are each independently a hydrogen atom, C 1 -C 5 alkyl group, C 3 -C 8 cycloalkyl group, C 1 -C 5 haloalkyl group, C 1 -C 3 alkoxy C 1 -C 4 Alkyl group, C 2 -C 6 alkenyl group, C 2 -C 6 haloalkenyl group, C 1 -C 4 alkylcarbonyl group, C 1 -C 4 haloalkylcarbonyl group, C 1 -C 4 alkylsulfonyl group, C 1- A C 4 haloalkylsulfonyl group, a C 1 -C 3 alkoxycarbonyl group or a C 1 -C 3 haloalkoxycarbonyl group;
  • C 1 ⁇ range of C 3 alkyl group an alkoxy group in C 1 ⁇ C 3 alkoxy C 1 ⁇ C 4 alkyl group are the same as those defined above definition.
  • C 1 ⁇ C 4 range of the alkyl group in C 1 ⁇ C 3 alkoxy C 1 ⁇ C 4 alkyl groups are the same as defined above definition, specifically, for example, C 1 ⁇ C 4 alkyl group Is an alkyl group which may be linear or branched, for example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group , T-butyl group and the like can be preferably listed.
  • preferred examples of the C 1 -C 3 alkoxy C 1 -C 4 alkyl group include a methoxymethyl group, an ethoxymethyl group, and a 2-methoxyethyl group.
  • the range of the C 1 -C 4 alkyl group in the C 1 -C 4 alkylcarbonyl group is as defined above.
  • Preferred examples of the C 1 -C 4 alkylcarbonyl group include acetyl group, propionyl group, isopropylcarbonyl group, and cyclopropylcarbonyl group.
  • the range of the C 1 -C 4 haloalkyl group in the C 1 -C 4 haloalkylcarbonyl group is that having a halogen atom as a substituent in the C 1 -C 4 alkyl group defined above.
  • C 1 -C 4 haloalkylcarbonyl group examples include a trifluoroacetyl group, a pentafluoropropionyl group, a trichloroacetyl group, a chloroacetyl group, a bromoacetyl group, and a 3-chloropropionyl group.
  • the range of the C 1 -C 4 alkyl group of the C 1 -C 4 alkylsulfonyl group is as defined above.
  • Examples of the C 1 -C 4 alkylsulfonyl group include a methylsulfonyl group, an ethylsulfonyl group, n -Propylsulfonyl group, isopropylsulfonyl group, cyclopropylsulfonyl group, n-butylsulfonyl group, isobutylsulfonyl group, s-butylsulfonyl group, t-butylsulfonyl group and the like can be preferably listed.
  • the range of the C 1 -C 4 haloalkyl group in the C 1 -C 4 haloalkylsulfonyl group is as described above, and examples of the C 1 -C 4 haloalkylsulfonyl group include a trifluoromethylsulfonyl group and a pentafluoroethylsulfonyl group.
  • Preferred examples include 2,2,2-trifluoroethylsulfonyl group, heptafluoro-n-propylsulfonyl group, heptafluoroisopropylsulfonyl group, nonafluoro-n-butylsulfonyl group, nonafluoro-s-butylsulfonyl group, etc. be able to.
  • C 1 ⁇ C 3 haloalkoxy group C 1 ⁇ C 3 haloalkoxycarbonyl groups are substituted by halogen atoms C 1 ⁇ C 3 alkoxy group as defined above is introduced as a substituent, C 1 ⁇ C
  • the 3 haloalkoxycarbonyl group include a chloromethoxycarbonyl group, a 2,2,2-trifluoroethoxycarbonyl group, a 3,3,3-trifluoropropyloxycarbonyl group, and a 3,3,3-trichloropropyloxy group.
  • a carbonyl group etc. can be enumerated suitably.
  • R 6 is preferably a hydrogen atom or a methyl group.
  • R 7 is preferably a hydrogen atom or a methyl group.
  • X represents a halogen atom.
  • X is preferably a fluorine atom.
  • Y is independently a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a C 1 -C 5 alkyl group (preferably a C 1 -C 3 alkyl group), a C 1 -C 5 haloalkyl group ( C 1 -C 3 haloalkyl group), C 1 -C 3 alkylamino group, di-C 1 -C 3 alkylamino group, C 1 -C 3 alkoxy group or C 1 -C 3 haloalkoxy group are preferred.
  • the range of the C 1 -C 5 alkyl group and the C 1 -C 3 alkyl group is the same as defined above, and the range of the C 1 -C 5 haloalkyl group or C 1 -C 3 haloalkyl group is also defined above. It is the same.
  • Preferable examples of the C 1 -C 3 alkyl group include a methyl group, an ethyl group, an n-propyl group, and an isopropyl group.
  • Preferred examples of the C 1 -C 3 haloalkyl group include a difluoromethyl group, a trifluoromethyl group, a pentafluoroethyl group, and the like.
  • the range of the C 1 -C 3 alkyl group in the C 1 -C 3 alkylamino group is the same as defined above, and the C 1 -C 3 alkylamino group may be linear or branched.
  • Suitable examples of the alkylamino group include a methylamino group, an ethylamino group, an n-propylamino group, and an isopropylamino group.
  • Range of C 1 ⁇ C 3 alkyl group in di C 1 ⁇ C 3 alkyl amino groups is similar to the above provisions, the di C 1 ⁇ C 3 alkyl group, a straight chain, be cyclic, branched Dialkylamino group optionally having, for example, dimethylamino group, methylethylamino group, diethylamino group, di-n-propylamino group, diisopropylamino group, dicyclopropylamino group, etc. be able to.
  • the definition of other groups is as defined above.
  • Y is preferably a hydrogen atom or a halogen atom.
  • Z is each independently a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a C 1 -C 5 alkyl group (preferably a C 1 -C 3 alkyl group), a C 1 -C 5 haloalkyl group, A C 1 -C 3 alkoxy group or a C 1 -C 3 haloalkoxy group;
  • a hydrogen atom is preferable.
  • n represents an integer of 0 to 3.
  • m represents an integer of 0-2.
  • the compound of the present invention may have a conformational isomer depending on the type of substituent, but the present invention also includes a mixture containing the conformer in an arbitrary ratio.
  • the compounds of the present invention may have optical isomers due to the presence of asymmetric carbon atoms, but the present invention also includes mixtures containing all optically active substances in any proportion. It is.
  • the compound of the present invention is a novel compound and can be produced, for example, according to the following synthesis schemes 1 to 4.
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , n, m, X, Y and Z are as defined in formula [1]
  • R 8 is The lower alkyl group is, for example, an alkyl group having about 1 to 5 carbon atoms, the range of which is as defined above, and Hal represents a halogen atom.
  • Compound [4] can be obtained by reacting compound [2] with compound [3]. This reaction can be carried out in the presence or absence of a solvent and a base.
  • the solvent is not particularly limited as long as it does not directly participate in this reaction.
  • aromatic hydrocarbons such as benzene, toluene and xylene; ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone; chloroform And halogenated hydrocarbons such as methylene chloride; esters such as methyl acetate and ethyl acetate; ethers such as tetrahydrofuran, dioxane, diethyl ether, and 1,2-dimethoxyethane; water; acetonitrile and N, N Polar solvents such as -dimethylformamide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide, or a mixed solvent of the
  • Organic bases such as triethylamine, pyridine, 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU), 4-dimethylaminopyridine as bases; alkalis such as sodium hydroxide and potassium hydroxide Metal hydroxides; alkaline earth metal hydroxides such as calcium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; alkaline earth metal carbonates such as calcium carbonate; alkali metal carbonates such as sodium hydrogen carbonate Hydrogen salt; metal alkoxides such as sodium methoxide and potassium ethoxide are listed.
  • the reaction temperature is, for example, ⁇ 30 ° C. to 150 ° C., preferably ⁇ 5 ° C. to 80 ° C.
  • the target product may be isolated from the reaction system by a conventional method. If necessary, the target product can be produced by purification by washing with a solvent, recrystallization, column chromatography or the like. Moreover, it is also possible to use for the next process, without isolating a target object from a reaction system.
  • Compound [2] is a known compound.
  • the aniline derivative represented by the general formula [3] which is a raw material compound of this reaction can be produced according to the production method disclosed in WO2005 / 021488 pamphlet, WO2005 / 073165 pamphlet, or WO2008 / 0754559 pamphlet. it can.
  • aromatic hydrocarbons such as benzene, toluene and xylene; ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone; chloroform And halogenated hydrocarbons such as methylene chloride; esters such as methyl acetate and ethyl acetate; ethers such as tetrahydrofuran, dioxane, diethyl ether, and 1,2-dimethoxyethane; water; acetonitrile and N, N Polar solvents such as -dimethylformamide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide; alcohols such as methanol, ethanol and isopropanol, or mixed solvents of the above solvents.
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • ketones such as acetone, methyl ethyl
  • bases include triethylamine, organic bases such as pyridine, 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU), 4-dimethylaminopyridine; sodium hydroxide, potassium hydroxide, etc.
  • Alkaline earth metal hydroxides such as calcium hydroxide; alkaline metal carbonates such as sodium carbonate and potassium carbonate; alkaline earth metal carbonates such as calcium carbonate; alkalis such as sodium bicarbonate Metal hydrogen carbonates; metal alkoxides such as sodium methoxide and potassium ethoxide.
  • the reaction temperature is, for example, ⁇ 30 ° C. to 150 ° C., preferably ⁇ 5 ° C. to 80 ° C.
  • the target product may be isolated from the reaction system by a conventional method. If necessary, the target product can be produced by purification by washing with a solvent, recrystallization, column chromatography or the like.
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , n, m, X, Y and Z are as defined in formula [1]
  • R 8 is Lower alkyl represents a lower alkyl group, for example, an alkyl group having about 1 to 5 carbon atoms, the range of which is as defined above.
  • Solvents include aromatic hydrocarbons such as benzene, toluene and xylene; ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone; halogenated hydrocarbons such as chloroform and methylene chloride; methyl acetate and ethyl acetate Esters such as tetrahydrofuran, dioxane, diethyl ether, 1,2-dimethoxyethane; water; acetonitrile, N, N-dimethylformamide, N-methylpyrrolidone, 1,3-dimethyl-2- Examples include polar solvents such as imidazolidinone and dimethyl sulfoxide; alcohols such as methanol, ethanol and isopropanol, and mixed solvents of the above solvents.
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • ketones such as acetone, methyl ethyl ket
  • Organic bases such as triethylamine, pyridine, 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU), 4-dimethylaminopyridine as bases; alkalis such as sodium hydroxide and potassium hydroxide Metal hydroxide; alkaline earth metal hydroxide such as calcium hydroxide; alkali metal carbonate such as sodium carbonate and potassium carbonate; alkaline earth metal carbonate such as calcium carbonate; alkali metal carbonate such as sodium hydrogen carbonate Hydrogen salt; metal alkoxides such as sodium methoxide and potassium ethoxide are listed.
  • alkalis such as sodium hydroxide and potassium hydroxide Metal hydroxide
  • alkaline earth metal hydroxide such as calcium hydroxide
  • alkali metal carbonate such as sodium carbonate and potassium carbonate
  • alkaline earth metal carbonate such as calcium carbonate
  • alkali metal carbonate such as sodium hydrogen carbonate Hydrogen salt
  • metal alkoxides such as sodium methoxide and potassium
  • the ester derivative represented by the general formula [6] which is a raw material compound for this reaction, can be produced according to the production method disclosed in WO2010 / 090282 pamphlet.
  • (2) Production of compound of general formula [1] Compound [1] is obtained by reacting compound [3] with compound [7]. This reaction can be carried out in the presence of a condensing agent, in the presence or absence of a solvent and a base.
  • the solvent is not particularly limited as long as it does not directly participate in this reaction.
  • aromatic hydrocarbons such as benzene, toluene and xylene; ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone; chloroform And halogenated hydrocarbons such as methylene chloride; esters such as methyl acetate and ethyl acetate; ethers such as tetrahydrofuran, dioxane, diethyl ether, and 1,2-dimethoxyethane; water; acetonitrile and N, N Polar solvents such as -dimethylformamide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide; alcohols such as methanol, ethanol and isopropanol, or mixed solvents of the above solvents.
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • ketones such as acetone, methyl ethyl
  • bases include triethylamine, organic bases such as pyridine, 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU), 4-dimethylaminopyridine; sodium hydroxide, potassium hydroxide, etc.
  • Alkaline earth metal hydroxides such as calcium hydroxide; alkaline metal carbonates such as sodium carbonate and potassium carbonate; alkaline earth metal carbonates such as calcium carbonate; alkalis such as sodium bicarbonate Metal hydrogen carbonates; metal alkoxides such as sodium methoxide and potassium ethoxide.
  • the reaction temperature is, for example, ⁇ 30 ° C. to 150 ° C., preferably ⁇ 5 ° C. to 80 ° C.
  • Examples of the condensing agent used in the reaction include 1,3-dicyclohexylcarbodiimide (DCC), 2-chloro-1-methylpyridinium iodide, carbonyldiimidazole (CDI), and trifluoroacetic anhydride. .
  • the reaction temperature is, for example, ⁇ 30 ° C. to 150 ° C., preferably ⁇ 5 ° C. to 80 ° C.
  • the target product may be isolated from the reaction system by a conventional method. If necessary, the target product can be produced by purification by washing with a solvent, recrystallization, column chromatography or the like.
  • aromatic hydrocarbons such as benzene, toluene and xylene; ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone; chloroform And halogenated hydrocarbons such as methylene chloride; esters such as methyl acetate and ethyl acetate; ethers such as tetrahydrofuran, dioxane, diethyl ether, and 1,2-dimethoxyethane; acetonitrile and N, N-dimethyl Examples thereof include polar solvents such as formamide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide, and mixed solvents of the above solvents.
  • polar solvents such as formamide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide, and mixed solvents of the above solvents.
  • the reaction temperature is, for example, ⁇ 30 ° C. to 150 ° C., preferably ⁇ 5 ° C. to 80 ° C.
  • the target product may be isolated from the reaction system by a conventional method. If necessary, the target product can be produced by purification with a solvent, distillation, recrystallization, column chromatography or the like.
  • the halogenating agent include thionyl chloride, thionyl bromide, phosphorus trichloride, phosphorus oxychloride, phosphorus pentachloride, oxalyl chloride, and the like.
  • This reaction can be carried out in the presence or absence of a solvent and a base.
  • the solvent is not particularly limited as long as it does not directly participate in this reaction, and for example, aromatic hydrocarbons such as benzene, toluene and xylene; ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone; chloroform and Halogenated hydrocarbons such as methylene chloride; esters such as methyl acetate and ethyl acetate; or ethers such as tetrahydrofuran, dioxane, diethyl ether, and 1,2-dimethoxyethane; water; acetonitrile and N, N Polar solvents such as dimethylformamide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide or a mixed solvent of the above solvents.
  • Organic bases such as triethylamine, pyridine, 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU), 4-dimethylaminopyridine as bases; alkalis such as sodium hydroxide and potassium hydroxide Metal hydroxide; alkaline earth metal hydroxide such as calcium hydroxide; alkali metal carbonate such as sodium carbonate and potassium carbonate; alkaline earth metal carbonate such as calcium carbonate; alkali metal carbonate such as sodium hydrogen carbonate Hydrogen salt; metal alkoxides such as sodium methoxide and potassium ethoxide are listed.
  • the reaction temperature is, for example, ⁇ 30 ° C. to 150 ° C., preferably ⁇ 5 ° C. to 80 ° C.
  • the target product may be isolated from the reaction system by a conventional method. If necessary, the target product can be produced by purification by washing with a solvent, recrystallization, column chromatography or the like.
  • Hal is Represents a halogen atom.
  • Compound [10] is obtained by reacting compound [8] with compound [9]. The above reaction can be carried out in the presence or absence of a solvent and a base.
  • Compound [9] is a known compound.
  • the solvent is not particularly limited as long as it does not directly participate in this reaction.
  • aromatic hydrocarbons such as benzene, toluene and xylene; ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone; chloroform And halogenated hydrocarbons such as methylene chloride; esters such as methyl acetate and ethyl acetate; ethers such as tetrahydrofuran, dioxane, diethyl ether and 1,2-dimethoxyethane; water; acetonitrile and N, N Polar solvents such as dimethylformamide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide, or a mixed solvent of the above solvents.
  • Organic bases such as triethylamine, pyridine, 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU), 4-dimethylaminopyridine as bases; alkalis such as sodium hydroxide and potassium hydroxide Metal hydroxide; alkaline earth metal hydroxide such as calcium hydroxide; alkali metal carbonate such as sodium carbonate and potassium carbonate; alkaline earth metal carbonate such as calcium carbonate; alkali metal carbonate such as sodium hydrogen carbonate Hydrogen salt; metal alkoxides such as sodium methoxide and potassium ethoxide are listed.
  • the reaction temperature is, for example, ⁇ 30 ° C. to 150 ° C., preferably ⁇ 5 ° C. to 80 ° C.
  • the target product may be isolated from the reaction system by a conventional method. If necessary, the target product can be produced by purification by washing with a solvent, recrystallization, column chromatography or the like. Moreover, it is also possible to use for the next process, without isolating a target object from a reaction system.
  • the above reaction can be carried out in the presence or absence of a solvent.
  • the solvent is not particularly limited as long as it does not directly participate in this reaction.
  • aromatic hydrocarbons such as benzene, toluene and xylene; ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone; chloroform And halogenated hydrocarbons such as methylene chloride; esters such as methyl acetate and ethyl acetate; ethers such as tetrahydrofuran, dioxane, diethyl ether, and 1,2-dimethoxyethane; acetonitrile and N, N-dimethyl
  • polar solvents such as formamide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide, and mixed solvents of the above solvents.
  • the reaction temperature is, for example, ⁇ 30 ° C. to 150 ° C., preferably ⁇ 5 ° C. to 80 ° C.
  • the target product may be isolated from the reaction system by a conventional method. If necessary, the target product can be produced by purification by washing with a solvent, recrystallization, column chromatography or the like.
  • the halogenating agent include thionyl chloride, thionyl bromide, phosphorus trichloride, phosphorus oxychloride, phosphorus pentachloride, oxalyl chloride, and the like.
  • Compound [1] is obtained by reacting compound [11] with compound [12].
  • the above reaction can be carried out in the presence or absence of a solvent and a base.
  • the solvent is not particularly limited as long as it does not directly participate in this reaction, and for example, aromatic hydrocarbons such as benzene, toluene and xylene; ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone; chloroform and Halogenated hydrocarbons such as methylene chloride; esters such as methyl acetate and ethyl acetate; or ethers such as tetrahydrofuran, dioxane, diethyl ether, and 1,2-dimethoxyethane; water; acetonitrile and N, N Polar solvents such as dimethylformamide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, 1,3-dimethyl-2-
  • Organic bases such as triethylamine, pyridine, 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU), 4-dimethylaminopyridine as bases; alkalis such as sodium hydroxide and potassium hydroxide Metal hydroxide; alkaline earth metal hydroxide such as calcium hydroxide; alkali metal carbonate such as sodium carbonate and potassium carbonate; alkaline earth metal carbonate such as calcium carbonate; alkali metal carbonate such as sodium hydrogen carbonate Hydrogen salt; metal alkoxides such as sodium methoxide and potassium ethoxide are listed.
  • the reaction temperature is, for example, ⁇ 30 ° C. to 180 ° C., preferably ⁇ 5 ° C. to 150 ° C.
  • the target product may be isolated from the reaction system by a conventional method. If necessary, the target product can be produced by purification by washing with a solvent, recrystallization, column chromatography or the like.
  • the aniline derivative represented by the general formula [12] which is a raw material compound for this reaction, can be produced according to the production method disclosed in WO2005 / 021488, WO2005 / 073165, or WO2008 / 07459. it can.
  • the insecticide and acaricide of the present invention containing the compound of the present invention represented by the formula [1] as an active ingredient is used for the prevention and extermination of harmful organisms in agriculture, indoors, forests, livestock, sanitation, etc. Can be done. Specific usage scenes, target pests, and usage methods are shown below, but the contents of the present invention are not limited to these.
  • the compound of the present invention can be used for agricultural crops such as food crops (rice, barley, wheat, rye, oats and other wheat, corn, potato, sweet potato, taro, soybeans, red beans, broad beans, peas, beans, peanuts, etc.
  • agricultural crops such as food crops (rice, barley, wheat, rye, oats and other wheat, corn, potato, sweet potato, taro, soybeans, red beans, broad beans, peas, beans, peanuts, etc.
  • vegetables such as Chinese cabbage, radish, persimmon, broccoli, cauliflower, cruciferous crops such as komatsuna, pumpkins, cucumbers, watermelons, mushrooms, melons and other cucumbers, eggplants, tomatoes, peppers, peppers , Okura, spinach, lettuce, lotus root, carrot, burdock, garlic, onion, green onion, etc.), fruit trees / fruits (apple, citrus, pear, strawberry, peach, plum, cherry peach, walnut, chestnut, almond, Bananas, strawberries, etc.), fragrances and other crops for viewing (lavender, rosemary, thyme, parsley, pepper, ginger, etc.), special crops (tobacco, tea, sugar beet, sugar) Millet, hop, cotton, hemp, olive, rubber, coffee, etc.), grass and feed crops (Timothy, clover, alfalfa, corn, sorghum, orchardgrass, grasses, legumes, etc.), turf Turf, bentgrass, etc.
  • Specific pests include the Lepidoptera of Arthropoda, for example, Helicoverpa armigera, Heliothis spp., Agrotis segetum, Autographa nigrisigna , Nettle moths (Trichoplusia ni), mushrooms (Mamestra ⁇ brassicae), Shirooptera exigua, Spodoptera litura, etc., Plutella xylostella, etc , Adoxophyes honmai, Midarekamonmonaki (Archips fuscocupreanus), Chamonaki (Homona magnanima), Chanohosoga (Caloptilia theivora), Nashihimeshinchi (Grapholita molesta), etc.
  • Ginger-buckthorn (Lyonetia prunifoliella malinella) Hamoguriga (Lyonetia clerkella), etc., etc. Kohamoguriga Department of oranges leafminer (Phyllocnistis citrella), the apple leaf miner of subfraction Department (Phyllonorycter ringoniella), etc.,
  • Coleoptera for example, Anomala cuprea, beetle (Popillia japonica), Oxycetonia jucunda, Anomala geniculata, and the like. , Ancholymaceae (Melanotus fortnumi), etc.
  • Aulacophora femoralis root worm species (Diabrotica spp.), Kiss beetle beetle (Phyllotreta striolata), beetle horn beetle (Cassida nebulosa), radish beetle (Phaedon brassicae), rice beetle moth (Oulema oryzae), pilican beetle Leptinotarsa decemlineata, etc., Rhynchites heros, etc., Cylas Adults, larvae and eggs, such as weevil (Anthonomus gradis grandis), Sphenophrus venatus vestitus, etc., Epuraea domina, etc.
  • Heteroptera from the order of the Hemiptera for example, Eurydema rugosum, Eysarcoris lewisi, Eysarcoris parvus, Nyra Stink bug (Plautia stali), Halymorpha mista, etc. , Cletus ig punctiger, etc., Leptocorisa chinensis, etc. Etc. Turtle (Apolygus spinolai), red streaks Kasumi turtle (Stenotus rubrovittalus), Trigonotylus caelestialium (Trigonotylus coelestialium), etc., beans stink bug family circle stink bug (Megacopta punctatissimum) adults such as, larvae and eggs:
  • Homoptera moths of the order of the Hemiptera for example, Platypleuraempkaempferi, etc. , Nephotettix virescens, etc.
  • Various biotypes of the whitefly Aleurocanthus spiniferus, silver leaf whitefly (Bemisia argentifolii), tobacco whitefly (Bemisia tabaci), etc.
  • Jirami Trialeurodes vaporariorum
  • Viteus vitifolii such as the phyllocera family, Aphis citricola, bean aphid (Aphis ⁇ ⁇ craccivora), cotton aphid (ynes) , Komikan Aphid (Toxoptera aurantii), Satsuma Aphid (Toxoptera citricidus), Elder Aphid (Aulacorthum magnoliae), Nymphaea (Schizaphis piricola), Nasipolionus aphid (Nippolachnus phipacon) Chrysanthemum aphid (Hyalopterus pruni), Chrysanthemum aphid (Pleotrichophorus chrysanthemi), Chrysanthemum aphid (Macrosiphoniella sanborni), Broad beetle aphid (Megoura crassicauda), Ibaragigenaga Aphids (Sitobion ibarae), tulip bee
  • Thysanoptera e.g., Thrips palma, Thripsella, Thripsella, Thripsella, Thripsella, Thripsella Yellow thrips (Frankliniella occidentalis), Croton thrips (Heliothrips haemorrhoidalis), etc .
  • Hymenoptera for example, Athalia rosae ruficornis, Arge pagana, etc., Arge mali, etc .
  • Adults, larvae and eggs such as Megachile nipponica nipponica, such as the ants of the ant family, Formica japonica:
  • Flies for example, Spodoptera soya Sayatamabaye (Asphondylia yushimai), etc. Drosophila suzukii, etc., the species of the leaf family, Liriomyza trifolii, Chromatomyia horticola, Agromyza oryzae, elia moth Adults, larvae and eggs such as (Delia antiqua):
  • Orthoptera for example, Ruspolia lineosa, etc., crickets, Truljalia hibinonis, etc., Gryllotalpa orientalis, etc., Oxya yezoensis, etc.
  • Larvae and eggs Adults, larvae and eggs such as the termites (Isoptera), for example, Odontotermes formosanus Adults, larvae and eggs of the order Dermaptera, for example, Labidura riparia of the family Carabidae: Collembola from the order of the Arthropoda elegans, for example, adults, larvae and eggs such as Sminthurus viridis, Onychiurus matsumotoi, etc .: Arthropod Crustacea Isopods (Isopada), for example, adults such as Armadillidium vulgare (Armadillidium vulgare), larvae and eggs:
  • arthropod arachnid Acari from the order of the arthropod arachnid, for example, Polyphagotarsonemus latus, Phytonemus pallidus, etc., Penthaleus major, etc., Brevipalpus lewisi), Southern spider mite (Brevipalpus phoenicis), etc. Oligonychus ununguis), Eotetranychus kankitus, Clover spider mite (Bryobia praetiosa), etc.
  • Archaenioglossa of molluscs for example, Pomacea canaliculata, for example, Plumonata, for example, Achatina fulica, slug for slugs (Meghimatium bilineatum), Merax gagates of the family Nymphalidae, Lehmannina valentiana, Acusta despecta sieboldiana, etc.
  • Tylenchida of the Linear Animal Phantoms for example, Ditylenchus destructor in the family Anguinidae, Tylenchorhynchus claytoni in the family Tylencorinx, etc. ), Minoregusarusenchu (Pratylenchus coffeae), etc.
  • Cryptococcus such as Criconema jaejuense, Anguinaceae Notchyylenchus acris, Aphelecchoides fragarriae, etc.
  • multi-needle nematode Xiphinema sp.
  • Torikodorusu family Yumihari nematodes Trichodorus sp.
  • the compound of the present invention is used indoors in buildings including ordinary houses, and it harms wood and its processed products such as wooden furniture, stored foods, clothes, books, etc., and controls pests that damage our lives.
  • Can also be used to Specific pests include termites of the Arthropoda class, for example, adults of the white-tailed termites (Cryptotermes domesticus) such as the white-tailed termites (Reticulitermes speratus) and the termites (Coptotermes formosanus) , Larvae and eggs:
  • Coleoptera for example, Sweeophilus zeamais, Sitophilus zeamais, etc.
  • Physcomitridae Tribolium castaneum
  • Hirataka kunustomododoki Tribolium confusum
  • scallop slatted beetle Oryzaephilus surinamensis
  • scallop squirrel Cryptolestes pusillus
  • rioderma sera (Stegobium paniceum), etc.
  • Attagenus unicolor japonicus Anthrenus verbasci
  • Dermestes maculatus etc.
  • Lion Gibbium aequinnoctiale etc. egg:
  • Lepidoptera for example, Cadra cautella, Ephestia kuehniella, Plodia interpunctella, etc., Sitotroga cerealella, etc., Tinea adults, larvae and eggs, such as translucens) and koiga (Tineola bisselliella): Chatteramidae, for example, adults, larvae and eggs such as Lepinotus reticulatus, Liposcelis bostrychophilus, etc .:
  • Cockroaches for example adults, larvae and eggs such as the cockroach (Blattella germanica), the cockroach (Periplaneta fuliginosa), the cockroach (Periplaneta japonica): Spots, for example adults, larvae and eggs such as Ctenolepisma villosa and Lepisma saccharina:
  • Examples of the mites of arthropod spiders include adults, larvae and eggs, such as Carroglyphus lactis, such as Tyrophagus putrescentiae, Lardoglyphus konoi, and the like.
  • the compounds of the present invention can also be used to control pests that damage or weaken trees in natural forests, artificial forests, and urban green spaces.
  • Specific pests include the Lepidoptera of Arthropoda, for example, Callitearagentargentata, Chauctoidea (Euproctis pseudoconspersa), Orygiawork approximans, Euproctis subflava, Maimai (Lymantria dispar), etc.
  • Coleoptera for example, Anomala rufocuprea, Heptophylla picea, etc., Agrilus spinipennis, etc., Monochamus alterna, Basilepta pallidula, etc., Weevil weevil (Scepticus griseus), Shirahoshizo insidiosus, etc., Weevil weevil (Sipalinus gigas), etc. aceris) and other adults, larvae and eggs such as Rhizopertha dominica: Stink bugs, for example, Cinara todocola (Aphididae), Adelges japonicus (Adelges japonicus), Asperiotus cryptomeriae, etc.
  • ceriferus and other adults, larvae and eggs: For example, adults, larvae and eggs of bees, for example, Pachynematus itoi, Nepipriser sertifer, Dryocosmus kuriohilus, etc.
  • flies for example, Tipula aino, etc., Strobilomyia laricicola, etc., Contarinia inouyei, Contarinia matsusintome, adults such as Contarinia matsusintome, etc. egg: For example, adults, larvae and eggs of arthropod spider mites, for example, Oligonichus hondoensis, Oligonichus ununguis: Examples of the linear animal genus genus Tilenx include, for example, Bursaphelenchus xylophilus belonging to the family Parasitaferenx.
  • the compound of the present invention is an arthropod that parasitizes internally or externally to domestic animals and pets such as cattle, sheep, goats, horses, pigs, poultry, dogs, cats and fish, which are vertebrates, particularly warm-blooded vertebrates. It can also be used to prevent, treat or control worms, nematodes, flukes, tapeworms, and protozoa.
  • the target animal species include rodents such as mice, rats, hamsters and squirrels, carnivores such as ferrets, avian pets such as ducks and pigeons, experimental animals, and the like.
  • fly order of Arthropoda insect class for example, Tabanus rufidens, Tabbyus ⁇ chrysurus, etc., Muscaiibezzii, Musca domestica, Stomoxys calcitrans, etc., Gasterophilus intestinalis, etc., Hyppodae ovis, etc., Oestrus ovis, etc., Aldrichina ⁇ ⁇ graham, etc.
  • the white fly (Megaselia spiracularis),
  • Fleas for example adult fleas (Pulex irritans), adult fleas (Ctenocephalides canis), larvae and eggs: Lice, for example, Haematopinidae suis, Haematopinidae eurysternus, etc., Damalinia bovis, etc.
  • Mite of the Arthropoda spider for example, Varroa jacobsoni, Mite, Haemaphysalis longicornis, Ixodes ovatus, Boophilus microplus, Tickling mb such as testudinarium), oriental mite (Ornithonyssus sylvialum), etc., Dermanyssus gallinae, etc. (Knemidocoptes mutans) and other adults, larvae and eggs such as Otodectes cynotis and Psoroptes communis:
  • Coleoptera of linear animal gates such as caterpillars, swine nematodes, swine lungworms, ciliate nematodes, bovine intestinal nodules, etc .:
  • Roundworm for example, swine roundworm, chicken roundworm, etc .
  • Species of striated vertebrate for example, Schistosoma japonicum, liver tetsu, deer buccal fluke, Westermann lung fluke, Japanese chicken egg fluke Cestiidae, for example, foliar, extended, Beneden, square, stabulata, and ringworms:
  • Root-flagellate of the Protozoan Panoflagellate for example, Histomonas, etc.
  • Protoflagellate for example, Leishmania, Trypanosoma, etc.
  • Multiflagellate for example, Giardia, etc.
  • Trichomonas for example, Trichomonas, etc .:
  • Meat quality amoeba such as Entamoeba
  • Examples include Pyroplasma subclasses of the sporeworm class, for example, Theilaria, Babesia, etc., and Subspores of the late sporeworm class, for example, Eimeria, Plasmodium, Toxoplasma, etc.
  • the compounds of the present invention can also be used to control pests that cause direct harm or discomfort to the human body, or to maintain public health for pests that carry or carry pathogens.
  • Specific pests include Lepidoptera of Arthropoda, for example, Sphrageidus similis, etc., Kunugiaansundans, etc., Paratha ⁇ ⁇ consocia, etc. Department of Takenohosokuroba (Artona martini), etc.
  • Coleoptera for example, Xanthochroa waterhousei, etc., Epicauta gorhani, etc., Paederus fuscipes, etc., Bees, for example, Vespa simillima xanthoptera, etc., Brachyponera chinensis, etc., Batozonellus annulatus, etc.,
  • Flies for example, Armygeres subalbatus, etc., Culicoides nipponensis, etc., Chironomus yoshimatsui, etc., Simulium nikkoense, etc. Hirosia humilis, etc., Musca domestica, etc., Fannia canicularis, etc., Phormia regina, etc., Sarcophaga peregrina, etc.
  • Fleas eg adult fleas (Pulex irritans)
  • larvae and eggs Cockroaches, for example, adults, larvae and eggs such as the German cockroach (Blattella germanica), the cockroach (Periplaneta americana), the black cockroach (Periplaneta fuliginosa), the cockroach (Periplaneta japonica) and the like:
  • Orthoptera for example, adults, larvae and eggs such as Diestrammena japonica and Diestrammena apicalis Lice, for example adult larvae and larvae such as the head lice (Pediculus humanus humanus), the head lice (Phthirius pubis), etc .
  • Stink bugs for example, adults, larvae and eggs of the genus Isyndus obscurus, such as Cimex lectularius: Adults, larvae and eggs of the order Arthropoda (Collembola), for example, Hypogastrura communis from the family Murabidae:
  • Mite of Arthropoda spiders for example, Ixodes persulcatus, Mite, Ornithonyssus bacoti, Phyemotes, Pyemotes, etc. ventricosus, etc., Aceticidae (Demodex folliculorum) etc., Dermotophagoides pteronyssinus, etc., Scaroptes scabiei, etc. :
  • Scorpions for example, adults, larvae and eggs such as Isometrus europaeus from the family Scorpionidae: Artemipods of the Arthropod Posterior and Lepidoptera, for example, adults, larvae and eggs, such as Scolopendra subspinipes mutilans, Scolopendra subspinipes japonica:
  • Gemini for example, adults, larvae and eggs such as the Gurlidaceae (Thereuronema hilgendofi): Artemipods of the arthropod diploid, for example, adults, larvae and eggs such as Oxidus gracilis Isopods of arthropod crustaceans, for example adults, larvae and eggs such as Porcellio scaber of the family Paramecidae:
  • Examples include annelids of annelids, for example, Haemadipsa zeylanica japonica.
  • the compounds of the present invention are particularly valuable in controlling pests that damage crops, natural forests, planted forests and urban greenery trees and ornamental plants, such as arthropods, gastropods, nematodes. .
  • the compounds of the present invention may be used in other commercially active formulations, such as insecticides, acaricides, nematicides, in their commercially useful formulations and use forms prepared by these formulations. It can also be present as a mixture with fungicides, synergists, plant regulators, baits or herbicides.
  • Use forms include wettable powders, granular wettable powders, aqueous solvents, emulsions, liquids, flowables such as suspensions in water, emulsions in water, capsules, powders, granules, baits, aerosols, etc. Possible.
  • the total amount of the compound of the present invention is usually 0.001 to 95% by mass, preferably 0.1 to 60% by mass.
  • the plant foliage is usually placed in a place where damage by these pests or where damage is likely to occur.
  • soil all layers are mixed, crop application, floor soil mixing, cell seedling treatment, planting hole treatment, plant root treatment, top dress, rice box treatment, water surface treatment, etc. It can also be absorbed and used. It can also be used by soaking seeds in chemicals, seed dressing, seed treatment such as calper treatment, application to nutrient solution in nutrient solution (hydroponic) cultivation, smoke, or trunk injection.
  • the amount of the compound of the present invention is preferably 0.1 to 1000 g per 10 ares. Apply 1-100g. In order to treat this, dilute with water in wettable powder, granule wettable powder, water solvent, emulsion, liquid, flowable preparation such as suspension in water, emulsion in water, capsules, etc. Depending on the type of plant to be used and the cultivation form / growth state, it is generally applied to crops and the like at an application rate of 10 to 1000 liters per 10 ares. Moreover, what is necessary is just to process to a crop etc. in the state of the formulation in a powder agent or an aerosol agent.
  • the preparation is not diluted or diluted in water.
  • the method of applying to plant stock or seedling nursery, etc., the method of spraying granules to the plant stock or seedling nursery, etc., powder, wettable powder, granulated water before sowing or transplanting A method of spraying Japanese sweets, granules, etc., and mixing with the whole soil, a method of spraying powder, wettable powder, wettable powder, granules, etc. before sowing or planting planting holes, crops, etc. Etc.
  • wettable powders Diluted with water in wettable powders, granular wettable powders, aqueous solvents, emulsions, liquids, flowables such as suspensions and emulsions in water, capsules, etc., generally 5 to 500 liters per 10 ares At the application rate, spread over the soil surface so that it is even throughout the area to be treated, or in the state of its formulation in the form of irrigation, powder, granules or baits, so that it is even throughout the area to be treated. What is necessary is just to spread on the soil surface. Spraying or irrigation may be done around seeds, crops or trees that you want to protect from harm. Further, the active ingredient can be mechanically dispersed by tilling during or after spraying.
  • the dosage form may differ depending on the application time, such as application at the time of sowing, application at the greening period, application at the time of transplantation, etc., for example, powder, granule wettable powder, granule It may be applied in a dosage form such as. It can also be applied by mixing with soil, and it can be mixed with soil and powder, granulated wettable powder or granules, for example, mixed with ground soil, mixed with soil covering, mixed with the entire soil. Alternatively, the culture medium and various preparations may be applied alternately in layers.
  • solid preparations such as jumbo agents, packs, granules, granule wettable powders, and liquid preparations such as flowables and emulsions are usually sprayed on flooded paddy fields.
  • an appropriate preparation can be sprayed and injected into the soil as it is or mixed with fertilizer.
  • a chemical solution such as emulsion or flowable as a source of water flowing into a paddy field such as a water mouth or an irrigation device, it can be applied in a labor-saving manner along with the supply of water.
  • Seed treatment methods include, for example, a method of immersing seeds in a liquid state without diluting or diluting a liquid or solid preparation and adhering and penetrating the drug, mixing a solid preparation or liquid preparation with seeds, Examples thereof include a method of dressing and adhering to the surface of the seed, a method of coating the seed by mixing with an adhesive carrier such as resin and polymer, and a method of spraying around the seed simultaneously with planting.
  • the “seed” for performing the seed treatment means a plant body at an early stage of cultivation used for plant propagation, for example, a seed, a bulb, a tuber, a seed bud, a stock bud, a basket, a bulb or a nutrient for cultivation of cuttings.
  • the “soil” or “cultivation carrier” of a plant in the case of application refers to a support for cultivating crops, particularly a support for growing roots, and the material is not particularly limited. Any material can be used as long as it can grow, so-called soil, seedling mat, water, etc. Specific materials include, for example, sand, pumice, vermiculite, diatomaceous earth, agar, gel material, polymer material, rock Examples include wool, glass wool, wood chips, and bark.
  • the irrigation treatment of the liquid drug or the granule spraying treatment to the seedling nursery is preferred.
  • the compounds of the present invention are also valuable in protecting wood (standing trees, fallen trees, processed wood, stored wood or structural wood) from harms such as termites or cucumbers.
  • oils, emulsions, wettable powders, powders, etc. used in this scene are other active compounds such as insecticides, acaricides, nematicides, fungicides, repellents or synergists.
  • the total amount of the compound of the present invention is 0.0001 to 95% by mass, preferably 0.005 to 10% by mass for oils, powders and granules, and emulsions and
  • the wettable powder and sol may contain 0.01 to 50% by mass.
  • the compound of the present invention can be used when storing products such as cereals, fruits, nuts, spices and tobacco as they are, in a powdered state or mixed in the product. It can be used to protect against harm from other species.
  • animal products skin, hair, wool, feathers, etc.
  • plant products cotton, paper, etc.
  • Lepidoptera, Coleoptera, Spots, Cockroaches, etc. in natural or converted state, such as Lepidoptera, Coleoptera, Spots, Cockroaches, etc. It can be protected from attacks, and can also be protected from attacks by Lepidoptera, Coleoptera, flies, ticks, etc. when storing food such as meat and fish.
  • These formulations can also be present as a mixture with other active compounds such as insecticides, acaricides, nematicides, fungicides, repellents or synergists, these formulations Among them, the compound of the present invention may be contained in a total amount of 0.0001 to 95% by mass.
  • the compounds of the present invention prevail or mediate diseases of arthropods, humans and livestock that parasitize the body surface of humans and livestock and cause direct harm such as skin feeding or blood sucking. It is valuable for the control or prevention of arthropods, nematodes, flukes, tapeworms, protozoa, and arthropods that cause discomfort to humans.
  • the compound of the present invention is mixed in a small amount in a meal or feed, or a suitable pharmaceutical composition that can be taken orally, such as a pharmaceutically acceptable carrier, a tablet containing a coating substance, Oral administration or spray as pills, capsules, pastes, gels, beverages, medicinal feeds, medicinal drinking water, medicinal supplements, sustained-release large pills, and other sustained-release devices that are held in the gastrointestinal tract It can be administered transdermally as powder, grease, cream, ointment, emulsion, lotion, spot-on, pour-on, shampoo and the like. In order to achieve such an effect, the compound of the present invention can generally be added in an amount of 0.0001 to 0.1% by mass, preferably 0.001 to 0.01% by mass.
  • a device for example, a collar, a medallion, an ear tag, or the like
  • a device for example, a collar, a medallion, an ear tag, or the like
  • a device for example, a collar, a medallion, an
  • beverage When administered orally as medicinal drinking water, the beverage is usually dissolved, suspended or dispersed in a suitable non-toxic solvent or water with a suspending or wetting agent such as bentonite or other excipients. is there.
  • a suspending or wetting agent such as bentonite or other excipients.
  • beverages also contain an antifoam agent.
  • Beverage formulations can generally contain 0.01-1.0% by weight, preferably 0.01-0.1% by weight, of the compounds of the invention.
  • capsules, pills or tablets containing a predetermined amount of the active ingredient are usually used.
  • the compound of the present invention When administered by animal feed, it can be dispersed homogeneously in the feed, used as a top dressing or in the form of pellets.
  • the compound of the present invention may contain, for example, 0.0001 to 0.05% by mass, preferably 0.0005 to 0.01% by mass, in the final feed.
  • a liquid carrier vehicle can be administered parenterally to animals by intragastric, intramuscular, intratracheal or subcutaneous injection.
  • the active compounds are preferably mixed with suitable vegetable oils, such as peanut oil, cottonseed oil.
  • suitable vegetable oils such as peanut oil, cottonseed oil.
  • Such a formulation can generally contain 0.05 to 50% by weight, preferably 0.1 to 5.0% by weight, of the compound of the invention. It can also be administered topically by mixing with a suitable carrier such as dimethyl sulfoxide or a hydrocarbon solvent. This formulation is applied directly to the external surface of the animal by spraying or direct injection.
  • the compound of the present invention can be used as an anthelmintic agent for arthropods that cause direct harm, or as an anthelmintic agent for arthropods that are mediators of diseases, as an oil agent against the surrounding environment in which these pests can be latent.
  • Spraying injecting, irrigating and applying emulsions, wettable powders, spraying powders, fumigants, mosquito coils, self-burning smokes, heating fumes such as chemical reaction fumes, fogging, etc.
  • Use for methods such as treatment of smoke, ULV, etc., installation of granules, tablets and poisonous bait, or dripping of floating powders, granules, etc.
  • stag beetles which are also agricultural and forest pests, in the same manner as described above, or for the flies and the like so that they are mixed in the feed of livestock.
  • a method of volatilizing the mosquitoes into the air with an electric mosquito trap is also effective.
  • the preparations in these use forms can exist as a mixture with other active compounds such as insecticides, acaricides, nematicides, fungicides, repellents or synergists.
  • the above preparation suitably contains the compound of the present invention in a total amount, for example, 0.0001 to 95% by mass.
  • the compound of the present invention can be present as a mixture with other active compounds.
  • active compounds such as arthropods, gastropods, nematodes, etc. that damage plants by using them in combination with compounds (insecticides) having insecticidal activity, acaricidal activity or nematocidal activity
  • insecticides having insecticidal activity, acaricidal activity or nematocidal activity
  • exemplary active compounds include organophosphorus agents such as azinphos-methyl, acephate, chlorpyrifos, diazinon, dichlorvos, dimeton-S-methyl.
  • Carbamates such as alanycarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbofuran, carbosulfan, ethiofencarb, fenobucarb, furothiocarb (Furathiocarb), isoprocarb, mesomil, metolcarb, pirimicarb, propoxur, thiodicarb, etc .:
  • Organochlorine agents such as aldrin, chlordane, DDT (p, p'-DDT), endosulfan, lindane, etc .:
  • Pyrethroids such as acrinathrin, allethrin, bifenthrin, cycloprothrin, cyfluthrin, cyhalothrin, cyphenothrin, cypermethrin, deltamethrin deltamethrin), etofenprox, fenpropathrin, fenvalerate, flucythrinate, flufenprox, fluvalinate, furamethrin, halofen Proxrin (halfenprox), imiprothrin permethrin, phenothrin, prallethrin, pyrethrin, resmethrin, silaful off Emissions (silafluofen), tefluthrin (tefluthrin), tralomethrin (tralomethrin), transfluthrin (transfluthrin), etc.:
  • Neonicotinoid agents such as acetamiprid, clothianidin, dinotefran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, etc .:
  • Insect growth regulators such as phenylbenzoyl urea agents, such as chlorfluazuron, diflubenzuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, Teflubenzuron, triflumuron, buprofezin, chromafenozide, halofenozide, methoxyfenozide, tebufenozide, cyromazine, etc .:
  • Juvenile hormone agents such as diofenolan, phenoxycarb, hydroprene, methoprene, pyriproxyfen, etc .
  • Insecticidal substances produced by microorganisms such as abamectin, emamectin-benzoate, ivermectin, lepimectin, milbemectin, nemadectin, nikkomycin , Spinetram, spinosad, BT, etc .:
  • Insecticidal substances derived from natural products such as anabasine, azadiractin, deguelin, fatty acid glycerides (decanolyoctanoylglycerol), hydroxypropylstarch, soy lecithin, lepimectin, Nicotine, nornicotine, sodium oleate (oreic acid sodium salt), machine oil (petroleum oil), propylene glycol mono fatty acid ester (propylene glycol monolaurate), rapeseed oil (rape oil), rotenone (rotenone), etc .:
  • insecticides include, for example, acetoprole, bensultap, cartap, thiocyclam, chlorantraniliprore, chlorfenapyr, diafenthiuron , Ethiprole, fipronil, flonicamid, flubenziamid, hydramethylnon, indoxacarb, metaflumizone, metaldehyde, nicotine sulfate nicotin sulfate, pymetrozine, pyridalyl, pyrifluquinqzon, spirotetramat, tolfenpyrad, triazamate, etc .:
  • Acaricides such as acequinocyl, amitraz, azocyclotin, benzoximate, bifenazate, binapacryl, phenisobromolate, chinomethionat, clomethionat Fentezine, cyenopyrafen, cyflumetofen, tricyclohexyl hydroxide, cyhexatin, dicochlor, dienochlor, etoxazole, fenazaflor, fenazaquin, fenazaquin Fenbutatin oxide, fenothiocarb, fenpyroximate, fluacrypyrim, hexythiazox, pyrimidifen (pirimidi) fen), polynactins, propargite, pyridaben, spirodiclofen, spiromesifen, tebufenpyrad, tetradifon, etc .:
  • Nematicides such as aluminum phosphide, benclothiaz, cadusafos, ethoprophos, fosthiazate, imicyafos, levamisol hydrochloride, methamifenfos (mesulfenfos) ), Carbam (metam-ammonium), methyl isocyanate (methyl isothiocyanate), morantel tartarate (moranteltartarate), oxamyl (oxamyl), etc .: Poisonous bait, for example
  • Examples include chlorophacinone, coumatetralyl, diphacinone, monofluoroacetate, warfarin and the like.
  • the compound of the present invention can be present as a mixture with other active compounds other than compounds having insecticidal activity, acaricidal activity or nematicidal activity. In order to control diseases and / or weeds that occur at the same time of use, it can be used in combination with a compound having fungicidal activity, herbicidal activity, or plant growth regulating activity, thereby reducing the control effort and reducing the dosage. Synergistic effects can be expected. Moreover, more effective control effects, such as a synergistic effect, can be expected by using a mixture with a repellent or a synergist.
  • active compounds include bactericides such as DD (1,3-dichloropropene), acibenzolar-S-methyl, amisulbrom, triil (anilazine), and azoxyst.
  • Robin azoxystrobin
  • basic copper sulfate basic copper sulfate
  • benomyl benomyl
  • benchthiavalicarb-isopropyl benthiazole
  • bitertanol bitertanol
  • blasticidin S blasticidin S
  • Boscalid bromuconazole, calcium carbonate, calcium polysulfide, captan, carbendazim, carpropamid, chinomethionat, Chloroneb, chloropicrin Rothalonyl (chlorothalonil), DBEDC (complex of bis (ethylenediamine) copper-bis- (dodecylbenzenesulfonic acid)), cupric hydro
  • bactericides such as DD (1,3-dichlor
  • Cyproconazole cyprodinil, dazomet, dichlofluanid, diclocymet, diclomezine, dietofencarb, difenocondimol, diifenoimole (Dimethomorph), dithane-stainless, dithianon, dodine, echlomezole, edifenphos, shiitake mycelium extract (extract from mushroom), fenamidone, Fenarimol, fenbuconazole, fenhexamid, fenoxanol, ferimzone, fluazinam, flumetover, flumetover, full Pikorido (fluopicolide),
  • Fluorimide Fluorimide, fluquinconazole, flusulfamide, flutolanil, fosetyl-AL, fhalide, fludioxonil, furametpyr, fluconazole , Hexaconazole, hydroxyioxazole, hymexazol, imibenconazole, iminoctadine acetate (iminoctadine-acetate), iminoctadine-DBS, ipconazole ), IBP (iprobenfos), iprodione (iprodione), iprovalicarb, isoprothiolane, kasugamycin, kresoxim-methyl, ma Kozebu (mancozeb), maneb (maneb), mancozeb (manzeb), mepanipyrim (mepanipyrim),
  • Mepronil metalaxyl, metam-ammonium, metam-sodium, metconazole, metasulfocarb, methyl bromide, methyl isothiocyanate ( methylisothiocyanate, metinominostrobin, mildiomycin, myclobutanil, organic sulfur nickel salt (nickel dimethyldithiocarbamate), orysastrobin, oxadixyl, organic copper (oxine-copper), oxolinic Oxolinic acid, oxpoconazole fumarate, oxycarboxin, oxytetracycline, pebulate, pefurazoate, pencycuron, Penthiopyrad, polycarbamate, polyoxin-B,
  • Polyoxins potassium hydrogen carbonate, probenazole, prochloraz, procymidone, propamocarb, propiconazole, propineb, pyraclosto Robin (pyraclostrobin), pyrazophos (pyrifenox) (pyrifenox), pyrimethanil (pyrimethanil), pyroquilon (pyroquilon), quintozene, silver (silver), simeconazole (sodium hydrogen carbonate), next Sodium hypochlorite, spiroxamine, streptomycin, sulfur, tebuconazole, tecloftalam, tetraconazole, thiabe Thiabendazole, thiadiazin, thifluzamide, thiophanate, thiophanate methyl, thiophanate-methyl, thiuram, tiadinil, tolclofos-methyl, tolylfluanid (tolylfluanid) ), Triadimefon, t
  • Compounds having herbicidal activity include, for example, aclonifen, acifluofen n-sodium, alachlor, alloxydim, amicarbazone, amidosulfuron, anilofos ), Ashram, atrazine, azimsulfuron, benfuresate, bensulfuron-methyl, bentazone, benthiocarb, benzobicyclon, benzo Benzofenap, bialaphos, bifenox, bromobutide, bromoxynil, butamifos, cafenstrole, calcium peroxide, cal Carbetamide, cinosulfuron, clomeprop, cyclosulfamuron, cyhalofop-butyl, daimuron, desmedipham, diclofopmethyl -methyl),
  • Diflufenican dimefuron, dimethametryn, dinoterb, diquat, diuron, esprocarb, ethprozin, ethoxysulfon, ethofumeron ), Etobenzanid, fenoxaprop-P-ethyl, fentrazamide, flutrazamide, flucarbazone, flufenacet, flurtamone, fluthiaset-methyl , Foramsulfuron, glufosinate-ammonium, glyphosate-isopropyl amine, glyphosate-trimesium, imazapyr, imazosul Ron (imazosulfuron),
  • Examples of compounds having a plant growth regulating action include 1-naphthylacetic acid (1-naphthylacetic acid), 4-CPA (4-CPA), benzylaminopurine, 6-benzylaminopurine, butralin, calcium chloride ( calcium chloride, calcium formate (calcium peroxide), calcium sulfate (calcium sulfate), chlormequat chloride, choline, cyanamide, cyclanilide, daminozide ), Decyl alcohol, dichlorjoprop, ethephon, etychlozate, flurprimidol, forclorfenuron, gibberellic acid, indolebutyric acid (Indolebutyric acid), maleic acid Potassium dorazide (maleic hydrazide potassium salt), mefenpyr, mepiquat chloride, oxine sulfate, ⁇ ⁇ ⁇ -hydroxyquinoline sulfate, paclobutrazol,
  • Repellents such as capsaicin, carane-3,4-diol, citronellal, deet, dimethyl phthalate, hinokitiol, limonene (Limonene), linalool, menthol, menthone, naphthalene, thiram, etc .: Synergists such as methylenedioxynaphthalene, naphthyl propynyl ether, nitrobenzyl thiocyanate, octachlorodipropyl ether, pentynyl phthalimide), phenyl salioxon, piperonyl butoxide, safrole, sesamex, sesamin, sulfoxide, triphenyl phosphate, valbutin, etc. Can be mentioned.
  • the present invention includes, for example, cytoplasmic polyhedrosis virus (CV), insect pox virus (Entomopox virus, EPV), granulosis virus (Granulosis virus, GV), nuclear polyhedrosis virus (Nuclear) virus preparations such as polyhedrosisVvirus ⁇ (NPV), Beauveria bassiana, Beauveria brongniartii, Monocrosporium phymatophagum, Paeciloosepas , Steinernema carpocapsae, Steinernema glaseri, Steinernema kushidai, Verticillium lecanii, etc.
  • microbicidal agricultural chemicals to be used as a nematode agent Agrobacterium Liu um radiobacter (Agrobacterium radiobactor),
  • biopesticides for example, Amblyseius californicus, Amblyseius cucumeris, Amblyseius degenerans, Aphidius colemani, Aphidoletes aphidimyza, Aphidoletes aphidimyza (Chrysoperia carnea), Dacnusa sibirica, Diglyphus isaea, Encarsia formosa, Eretmocerus eremicus, Arpis ris rid , Hemiptarsenus varicornis, Nechrysocharis formosa, Orius sauteri, Orius strigicollis, Phytoseiulus persimilis , Black gourd turtles (Pilophorus typicus), Piocoris varius, and other natural enemies, codlelure, cuelure, geraniol, gyptol, liblure, loopure, loopure It can
  • Example 2- (1) Synthesis of 2-ethyl-4- (1-bromo-1,1,2,3,3,3-hexafluoroisopropyl) aniline Dissolve 24.2 g of 2-ethylaniline in 200 ml of ethyl acetate, 400 ml of water, sodium hydrosulfite 41.8 g, 20.2 g of sodium hydrogen carbonate, and 5 g of tetrabutylammonium hydrogen sulfate were sequentially added, and 62.0 g of 1,2-dibromo-1,1,2,3,3,3-hexafluoropropane was added dropwise.
  • Example 2- (2) 2-Fluoro-3- (N- (2,2,2-trifluoroethyl) -N-methylaminooxalylamino) -N- (2-bromo-4- (1-bromo-1,1,2,3) , 3,3-Hexafluoroisopropyl) -6-ethyl) phenylbenzamide (Compound No.1-55) 2-Bromo-4- (1-bromo-1,1,2,3,3,3-hexa) Fluoroisopropyl) -6-ethylaniline (0.30 g) and 2-fluoro-3- (N- (2,2,2-trifluoroethyl) -N-methylaminooxalylamino) benzoyl chloride (0.27 g) were added to 1,3-dimethyl- After dissolving in 0.8 ml of 2-imidazolidinone and stirring at room temperature overnight, an aqueous sodium hydrogen carbonate solution was added, extracted with ethy
  • Example 3- (1) Synthesis of 2-chloro-4- (1-bromo-1,1,2,3,3,3-hexafluoroisopropyl) -6-ethylaniline 2-ethyl-4- (1-bromo-1,1,2 , 3,3,3-hexafluoroisopropyl) aniline dissolved in 20 ml of N, N-dimethylformamide, 4.70 g of N-chlorosuccinimide was added, stirred for 2 hours, water was added to the reaction solution, and the mixture was extracted with ethyl acetate.
  • Example 4- (1) Synthesis of 2-iodo-4- (1-bromo-1,1,2,3,3,3-hexafluoroisopropyl) -6-ethylaniline 2-ethyl-4- (1-bromo-1,1,2 , 3,3,3-hexafluoroisopropyl) aniline dissolved in 20 ml of N, N-dimethylformamide, added with 7.43 g of N-iodosuccinimide, stirred for 3 hours, added water to the reaction solution, and extracted with ethyl acetate.
  • Example 5- Synthesis of 2-bromo-4- (1-bromo-1,1,2,3,3,3-hexafluoroisopropyl) -6-methylaniline 2-methyl-4- (1-bromo-1,1,2 , 3,3,3-hexafluoroisopropyl) aniline dissolved in 20 ml of N, N-dimethylformamide, 5.88 g of N-bromosuccinimide was added, and the mixture was stirred for 2 hours.
  • Example 6- (1) Synthesis of N- (1,1,1-trifluoro-2-propyl) -ethoxyoxalylamide 12.00 g of 1,1,1-trifluoro-2-propylamine is diluted with 150 ml of tetrahydrofuran and 15.5 ml of triethylamine is added. While stirring with ice cooling, 13.65 g of ethyl oxalyl chloride was diluted with 20 ml of tetrahydrofuran and added dropwise. After completion of the dropwise addition, dilute hydrochloric acid and ethyl acetate are added to the reaction solution, and the mixture is separated.
  • Example 6- (2) Synthesis of N- (1,1,1-trifluoro-2-propyl) -N-methyl-ethoxyoxalylamide 2.48 g of 60% sodium hydride was suspended in 80 ml of N, N-dimethylformamide and ice-cooled. 12.19 g of N- (1,1,1-trifluoro-2-propyl) -ethoxyoxalylamide was added. After foaming was completed, 9.8 g of methyl iodide was diluted with 20 ml of N, N-dimethylformamide and added. After stirring at 50 ° C. for about 2 hours, N, N-dimethylformamide and the like are distilled off under reduced pressure.
  • Example 6- (3) Synthesis of N- (1,1,1-trifluoro-2-propyl) -N-methylaminooxamic acid N- (1,1,1-trifluoro-2-propyl) -N-methyl-ethoxyoxalamide 8.12 g was suspended in 14 ml of methanol and 5 ml of water, and 10.67 g of a 15% aqueous sodium hydroxide solution was added dropwise with ice cooling, followed by stirring for 1 hour. Concentrated hydrochloric acid (3.6 ml) was added to acidify the reaction solution and t-butyl methyl ether was added to separate the solution.
  • Example 6- (4) Synthesis of N- (1,1,1-trifluoro-2-propyl) -N-methylaminooxalyl chloride N- (1,1,1-trifluoro-2-propyl) -N-methylaminooxamic acid 1.17 g was suspended in 3 ml of toluene, 0.10 g of N, N-dimethylformamide and 2 ml of thionyl chloride were added, and the mixture was stirred for 4 hours at a bath temperature of 90 ° C.
  • Example 6- 2-Fluoro-3- (N- (1,1,1-trifluoro-2-propyl) -N-methylaminooxalylamino) benzoic acid Synthesis of Compound (No. 2-10) 2-Fluoro-3- Suspend 1.09 g of aminobenzoic acid in 8 ml of water, add 1.40 g of 20% aqueous sodium hydroxide and 1.0 g of sodium hydrogen carbonate, and add N- (1,1,1-trifluoro-2-propyl) -N-methyl. Aminooxalyl chloride was added dropwise under ice-cooling and stirred overnight.
  • Example 6- 2-Fluoro-3- (N- (1,1,1-trifluoro-2-propyl) -N-methylaminooxalylaminobenzoyl chloride Synthesis of Compound (No. 3-10) 2-Fluoro-3- (N -(1,1,1-trifluoro-2-propyl) -N-methylaminooxalylamino) benzoic acid 0.25 g was suspended in thionyl chloride 1.5 ml, heated and refluxed for 3 hours to remove excess thionyl chloride from the reaction mixture. And the like, and toluene was added to the residue.
  • Example 7- (3) Synthesis of N- (2,2-difluoroethyl) -N-methylaminooxamic acid Suspend 17.2 g of N- (2,2-difluoroethyl) -N-methyl-ethoxyoxalamide in 30 ml of methanol and 10 ml of water Under ice cooling, 19.4 g of a 20% aqueous sodium hydroxide solution was added dropwise and stirred for 1 hour. Concentrated hydrochloric acid is added to acidify the reaction solution, and t-butyl methyl ether is added to separate the solution.
  • Example 7- (4) Synthesis of N- (2,2-difluoroethyl) -N-methylaminooxalyl chloride 1.17 g of N- (2,2-difluoroethyl) -N-methylaminooxamic acid was suspended in 3 ml of toluene, and N, N -Dimethylformamide (0.10 g) and thionyl chloride (2 ml) were added, and the mixture was stirred at a bath temperature of 90 ° C for 4 hours. -Methylaminooxalyl chloride (oil) was obtained. 1 H-NMR (CDCl3), ⁇ ppm: (3.16 + 3.20) (3H, s), 3.70-3.81 (2H, m), 5.81-6.14 (1H, m)
  • Example 8- (1) Synthesis of 2-fluoro-3- (N-ethyl-N-methylaminooxalylamino) benzoic acid compound (No. 3-2) Suspension of 1.01 g of 2-fluoro-3-aminobenzoic acid in 8 ml of water 1.26 g of sodium bicarbonate was added, and 1.15 g of N-ethyl-N-methylaminooxalyl chloride was added dropwise under ice-cooling, and the mixture was stirred overnight. Crystals precipitated as acidified by adding concentrated hydrochloric acid to the reaction solution were filtered, washed with water, and dried. As a result, 1.54 g (solid) of the compound shown in Table 3 (No.
  • Example 9 The compounds of the present invention were prepared in the same manner as in Examples 1-8.
  • Table 1 shows representative compounds of the compounds of the present invention produced by Examples, but the present invention is not limited to these.
  • the compounds shown in Tables 2, 3, 4 and 5 are intermediates for the production of the compounds of the present invention.
  • Me is a methyl group
  • Et is an ethyl group
  • Pr is a propyl group
  • Bu is a butyl group
  • "n-" is normal
  • t-" is tertiary
  • i-” is iso
  • c-” is cyclo.
  • Table 6 below shows the physical property values of the compounds described in Tables 1 to 5 by 1 H-NMR.
  • a part represents a mass part.
  • Emulsion Compound of the present invention (10 parts), xylene (60 parts), N-methyl-2-pyrrolidone (20 parts) and Solpol 3005X (mixture of nonionic surfactant and anionic surfactant, Toho Chemical Industry Co., Ltd. (trade name) (10 parts) was uniformly mixed and dissolved to obtain an emulsion.
  • Formulation Example 2 Wettable powder-1 Compound of the present invention (20 parts), Nipseal NS-K (white carbon, Tosoh Silica Co., Ltd., trade name) (20 parts), Kaolin clay (Kaolinite, Takehara Chemical Co., Ltd., trade name) (20 parts) Sun extract P-252 (sodium lignin sulfonate, Nippon Paper Chemicals Co., Ltd., trade name) (5 parts) and Lunox P-65L (alkyl allyl sulfonate, Toho Chemical Co., Ltd., trade name) (5 parts) was uniformly mixed and ground with an air mill to obtain a wettable powder.
  • Nipseal NS-K white carbon, Tosoh Silica Co., Ltd., trade name
  • Kaolin clay Kaolin clay
  • Sun extract P-252 sodium lignin sulfonate, Nippon Paper Chemicals Co., Ltd., trade name
  • Lunox P-65L alkyl allyl sulfonate,
  • Formulation Example 3 Wetting Agent-2 Compound of the present invention (20 parts), nip seal NS-K (20 parts), kaolin clay (50 parts), LUNOX 1000C (naphthalene sulfonate condensate, Toho Chemical Co., Ltd., trade name) (5 parts) and Solpol 5276 (nonionic surfactant, Toho Chemical Co., Ltd., trade name) (5 parts) was uniformly mixed and pulverized with an air mill to obtain a wettable powder.
  • LUNOX 1000C naphthalene sulfonate condensate, Toho Chemical Co., Ltd., trade name
  • Solpol 5276 nonionic surfactant, Toho Chemical Co., Ltd., trade name
  • Formulation Example 4 Sol (Flowable) -1 Premixed propylene glycol (5 parts), Solpol 7933 (anionic surfactant, Toho Chemical Co., Ltd., trade name) (5 parts), compound of the present invention (20 parts) in water (50 parts) was dispersed into a slurry mixture, and then this slurry mixture was wet pulverized with Dynomill (Shinmaru Enterprises Co., Ltd.), and then xanthan gum (0.2 parts) was mixed and dispersed in water (19.8 parts) in advance. Was added to obtain a sol agent (flowable agent).
  • Sol (Flowable) -1 Premixed propylene glycol (5 parts), Solpol 7933 (anionic surfactant, Toho Chemical Co., Ltd., trade name) (5 parts), compound of the present invention (20 parts) in water (50 parts) was dispersed into a slurry mixture, and then this slurry mixture was wet pulverized with Dynomill (Shinmaru Enterprises Co., Ltd.),
  • Test Example 1 Insecticidal effect on larvae of diamondback moths Seedling seeds were sown in a jiffy pot and nurtured for 3 weeks. A water-diluted solution of the emulsion prepared according to Formulation Example 1 was sufficiently sprayed on the leaves of this pot planted plant using an air brush (1 concentration, 1 repetition). After the chemical solution was air-dried, it was kept in a thermostatic chamber at 25 ° C., and after 5 days of larvae, mortality and bitterness of the larvae were investigated, and the insecticidal rate (%) was determined by dying the bitter worm.
  • the description compound A of WO2010 / 090282 pamphlet (patent document 1) was used as a comparative compound.
  • Comparative Compound A did not exhibit insecticidal activity at a concentration of 0.78 ppm.
  • the compounds No. 1-1, 1-23, 1-28, 1-35, 1-36, 1-51, 1-53, 1-54, 1-56, 1-58 of the present invention are The insecticidal rate was 100% at a concentration of 0.78 ppm.
  • Test Example 2 Test for insecticide against spider mite A 430 ml polyethylene cup filled with water was capped with a hole (diameter: about 5 mm) in the center. A notch with a width of about 5 mm was cut into a circular filter paper having a diameter of 6.5 cm, and a strip-like portion hanging downward was inserted so as to be immersed in the water in the cup through a hole in the lid, and absorbent cotton was placed on the filter paper. In this way, place two leaf discs (2 cm ⁇ 5 cm) made from kidney bean primary leaves on absorbent cotton that has been constantly replenished with water in the cup, and 10 female adults of spider mite on the leaf disc. Vaccinated.
  • This cup was placed in an acrylic cylinder having a height of 50 cm and a diameter of 10 cm, and an aqueous dilution of an emulsion prepared according to Formulation Example 1 was sprayed with 1.35 ml per cup using an airbrush (one concentration, one repetition). . After spraying, it was kept in a constant temperature room at 25 ° C. Four days after the treatment, the life and death of adult worms and bitter melon were investigated under the binocular, and the morbidity (%) was determined by dying the bitter worm. In addition, the description compound A of WO2010 / 090282 pamphlet was used as a comparative compound.
  • Comparative Compound A did not show insecticidal activity at a concentration of 3.1 ppm.
  • the compounds Nos. 1-18, 1-35, 1-36, 1-48, 1-51, 1-53, 1-56, and 1-58 of the present invention are 100% at a concentration of 3.1 ppm. The insecticidal rate was shown.
  • Test Example 3 Insecticidal effect on larvae of peach aphid Three adult peach aphids were inoculated into 3 cm x 4 cm chopped leaf pieces and allowed to lay for 48 hours in a constant temperature room at 25 ° C. After removing the adults, the leaf pieces were immersed for 5 seconds in a water dilution of an emulsion prepared according to Formulation Example 1 and kept in a constant temperature room at 25 ° C. On the 7th day after the treatment, the mortality and bitterness of the nymph were investigated, and the insecticidal rate (%) was determined by dying the bitter worm. In addition, the description compound A of WO2010 / 090282 pamphlet was used as a comparative compound.
  • Comparative Compound A did not exhibit insecticidal activity at a concentration of 0.78 ppm.
  • the compounds No. 1-18 and 1-48 of the present invention showed 100% insecticidal rate at a concentration of 0.78 ppm.

Abstract

La présente invention concerne un dérivé de 3-aminooxalylaminobenzamide à utiliser dans un agent insecticide et acaricide; et l'un de ses intermédiaires. Le dérivé de 3-aminooxalylaminobenzamide est représenté par la formule [1] [où chacun des radicaux R1 et R2 représente un groupement alkyle en C1-5, un atome d'halogène, etc.; chacun des radicaux R3 et R4 représente indépendamment un groupement alkyle en C1-8, halogénoalkyle en C1-8, etc.; R5 représente un groupement halogénoalkyle en C1-5 ; chacun des radicaux R6 et R7 représente un atome d'hydrogène, un groupement alkyle en C1-5, etc.; X représente un atome d'halogène; Y représente un atome d'hydrogène, un atome d'halogène, etc.; Z représente un atome d'hydrogène, etc.; n représente un entier compris entre 0 et 3 inclus; et m représente un entier compris entre 0 et 2 inclus].
PCT/JP2010/072197 2010-12-10 2010-12-10 Dérivé de 3-aminooxalylaminobenzamide et agent insecticide et acaricide l'incluant en tant que principe actif WO2012077221A1 (fr)

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WO2014069665A1 (fr) 2012-11-05 2014-05-08 三井化学アグロ株式会社 Composition pour extermination de parasites animaux et procédé d'extermination de parasites animaux
WO2014122083A1 (fr) 2013-02-06 2014-08-14 Bayer Cropscience Ag Dérivés de pyrazole halosubstitués en tant qu'agents phytosanitaires
WO2015101622A1 (fr) 2014-01-03 2015-07-09 Bayer Cropscience Ag Nouveaux pyrazolyl-hétéroarylamides utilisables comme pesticides
WO2016008830A1 (fr) 2014-07-15 2016-01-21 Bayer Cropscience Aktiengesellschaft Aryl-triazolyl-pyridines en tant que pesticides
WO2016143650A1 (fr) * 2015-03-06 2016-09-15 住友化学株式会社 Composé 3-aminooxalylaminobenzamide et son utilisation pour lutter contre des arthropodes nuisibles
WO2016143652A1 (fr) * 2015-03-06 2016-09-15 住友化学株式会社 Composé 3-aminooxalylaminobenzamide et son utilisation pour la lutte contre des arthropodes nuisibles
WO2016163383A1 (fr) * 2015-04-09 2016-10-13 住友化学株式会社 Composé d'oxalyl amide et son utilisation pour la lutte contre les arthropodes nuisibles
WO2016163379A1 (fr) * 2015-04-09 2016-10-13 住友化学株式会社 Composé amide d'oxalyle et son utilisation pour la régulation d'arthropodes nuisibles
WO2017026298A1 (fr) * 2015-08-10 2017-02-16 住友化学株式会社 Composé amide d'oxalyle et son utilisation pour lutter contre les arthropodes nuisibles
WO2019214588A1 (fr) 2018-05-11 2019-11-14 沈阳化工大学 Composé benzamide et son application

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Cited By (15)

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US9381174B2 (en) 2012-11-05 2016-07-05 Mitsui Chemicals Agro, Inc. Composition and method for exterminating animal parasite
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WO2014069665A1 (fr) 2012-11-05 2014-05-08 三井化学アグロ株式会社 Composition pour extermination de parasites animaux et procédé d'extermination de parasites animaux
JPWO2014069665A1 (ja) * 2012-11-05 2016-09-08 三井化学アグロ株式会社 動物寄生虫駆除用組成物及び動物寄生虫の駆除方法
EP2915530A4 (fr) * 2012-11-05 2016-04-06 Mitsui Chemicals Agro Inc Composition pour extermination de parasites animaux et procédé d'extermination de parasites animaux
WO2014122083A1 (fr) 2013-02-06 2014-08-14 Bayer Cropscience Ag Dérivés de pyrazole halosubstitués en tant qu'agents phytosanitaires
WO2015101622A1 (fr) 2014-01-03 2015-07-09 Bayer Cropscience Ag Nouveaux pyrazolyl-hétéroarylamides utilisables comme pesticides
WO2016008830A1 (fr) 2014-07-15 2016-01-21 Bayer Cropscience Aktiengesellschaft Aryl-triazolyl-pyridines en tant que pesticides
WO2016143650A1 (fr) * 2015-03-06 2016-09-15 住友化学株式会社 Composé 3-aminooxalylaminobenzamide et son utilisation pour lutter contre des arthropodes nuisibles
WO2016143652A1 (fr) * 2015-03-06 2016-09-15 住友化学株式会社 Composé 3-aminooxalylaminobenzamide et son utilisation pour la lutte contre des arthropodes nuisibles
WO2016163383A1 (fr) * 2015-04-09 2016-10-13 住友化学株式会社 Composé d'oxalyl amide et son utilisation pour la lutte contre les arthropodes nuisibles
WO2016163379A1 (fr) * 2015-04-09 2016-10-13 住友化学株式会社 Composé amide d'oxalyle et son utilisation pour la régulation d'arthropodes nuisibles
WO2017026298A1 (fr) * 2015-08-10 2017-02-16 住友化学株式会社 Composé amide d'oxalyle et son utilisation pour lutter contre les arthropodes nuisibles
WO2019214588A1 (fr) 2018-05-11 2019-11-14 沈阳化工大学 Composé benzamide et son application
US11407711B2 (en) 2018-05-11 2022-08-09 Metisa Biotechnology Co., Ltd. Benzamide compound and use thereof

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