WO2020251012A1

WO2020251012A1 - Novel 1-benzylamine derivative and agricultural and horticultural agent using same as active ingredient

Info

Publication number: WO2020251012A1
Application number: PCT/JP2020/023191
Authority: WO
Inventors: 響八田; 一秋小山; 恒一荒木; 祥森下; 福地　俊樹
Original assignee: アグロカネショウ株式会社
Priority date: 2019-06-13
Filing date: 2020-06-12
Publication date: 2020-12-17
Also published as: JP2022116370A

Abstract

Provided is are an agricultural and horticultural agent, in particular a compound which is useful as the active ingredient of an agricultural and horticultural pest control agent, a mite control agent, a nematode control agent or a disease control agent. Specifically, a 1-benzylamine derivative represented by formula (1) or (2), N-oxide thereof, or a salt thereof.　In the formula, R¹ is, for example, a C_1-6 alkyl group or a halo- C_1-6 alkyl group, n is 1, X is, for example, a C_1-6 alkyl group, a C_1-6 halo-alkyl group, a halogen atom or a cyano group, R^2a, R^2b, R^2c and R^2d are, for example, hydrogen atoms, J¹ and J² are direct bonds or -alkylene groups, M are -alkylene groups or -NR⁵-, -O-, -S-, -S(O)-, or -S(O)₂-, R⁵ is, for example, a C_1-6 alkyl group or the like, R⁶ and R⁷ are, for example, hydrogen atoms or C_1-6 alkyl groups.

Description

New 1-benzylamine derivative and agricultural and horticultural chemicals containing it as an active ingredient

The present invention relates to a novel 1-benzylamine derivative and an agricultural and horticultural agent containing the compound as an active ingredient, particularly an agricultural and horticultural pest control agent, a mite control agent, a nematode control agent, or an agricultural and horticultural disease control agent, and the like. It is about how to use.

In the field of agriculture and horticulture, plant pest control agents for controlling various pests have been developed and put into practical use. However, the emergence of pests or diseases that have acquired drug resistance has become a problem, and the development of new drugs is eagerly desired.
Patent Document 1 describes that a 1-benzylpiperidine derivative is useful as an acaricide for animals. However, Patent Document 1 does not disclose a compound in which a sulfur substituent as in the present invention is specifically introduced as a substituent at the 5-position of the phenyl group of the 1-benzylpiperidin derivative. Furthermore, as a result of additional tests on the compounds described in Patent Document 1, it was found that their effects on spider mites were insufficient.
In addition, the following compounds are disclosed as compound analogs of the present invention (for example, Patent Documents 2 to 3). However, all of these compounds disclosed in Patent Documents 2 to 3 have different chemical structures from the compounds of the present invention.

US 2009/0082389 A1 Japanese Unexamined Patent Publication No. 2014-108943 International Publication No. 2018/05 1252

In crop production such as agriculture and horticulture, the damage caused by pests and diseases is still large, and the development of new agricultural and horticultural chemicals is desired due to factors such as the outbreak of pests resistant to existing drugs.

As a result of diligent research to solve the above problems, the present inventors have found that a 1-benzylamine derivative represented by the following formula (I), which is a novel compound not described in the literature, is a pest for agricultural and horticultural agents, especially agricultural chemicals. The present invention has been completed by finding that it is useful as a horticultural pest control agent, a mite control agent, a nematode control agent or a disease control agent.
That is, the present invention relates to an agricultural and horticultural drug containing a 1-benzylamine derivative represented by the following formulas (1) to (2), its N-oxide or a salt thereof as an active ingredient, a method of using the same, and a method of producing the same. It is a thing.
Equation (1):

[During the ceremony,
R ¹ is C _1-6 alkyl group, C _1-6 haloalkyl group, C _2-6 alkenyl group, C _2-6 haloalkenyl group, C _2-6 alkynyl group, C _2-6 haloalkynyl group, C _{3 -6} Cycloalkyl C _1-6 alkyl group or C _3-6 halocycloalkyl C _1-6 alkyl group,
n indicates an integer from 0 to 2
X is, C _1-6 alkyl, C _1-6 haloalkyl group, C _3-6 cycloalkyl alkyl groups, C _2-6 alkenyl groups, C _2-6 alkynyl group, C _2-6 haloalkenyl, C _{2- 6} Haloalkynyl group, C _1-6 alkoxy group, C _1-6 haloalkoxy group, C _3-6 halocycloalkyl group, C _1-6 alkyloxycarbonyl group, C _1-6 alkoxymethyl group, formyl group, Indicates a halogen atom, cyano group or nitro group,
Y represents a hydrogen atom, a halogen atom, a C _1-6 alkyl group or a C _1-6 haloalkyl group.
R ^2a , R ^2b , R ^2c and R ^2d may be the same or different, respectively, and represent a hydrogen atom, a halogen atom, a C _1-6 alkyl group or a C _1-6 haloalkyl group.
J ¹ indicates direct binding, CR ^3a R ^3b -or -CR ^3a R ^3b -CR ^3c R ^3d-
J ² indicates direct binding or -CR ^3e R ^3f-
R ^3a , R ^3b , R ^3c , R ^3d , R ^3e and R ^3f may be the same or different, respectively, and represent a hydrogen atom, a halogen atom, a C _1-6 alkyl group or a C _1-6 haloalkyl group.
M indicates -CR ^4a R ^4b- , -NR ^5- , -O-, -S-, -S (O)-or -S (O) _2- ,
R ^4a and R ^4b may be the same or different, respectively, and represent a hydrogen atom, a halogen atom, a C _1-6 alkyl group, a C _1-6 haloalkyl group, a cyano group or a C _1-6 alkoxycarbonyl group.
R ⁵ is a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _1-6 alkoxycarbonyl group, a C _1-6 alkylcarbonyl group, a C _1-6 haloalkylcarbonyl group, a C _1-6 alkylsulfonyl group or C _1-6 shows a haloalkylsulfonyl group. ], Or

Equation (2):

[During the ceremony,
R ¹ is C _1-6 alkyl group, C _1-6 haloalkyl group, C _2-6 alkenyl group, C _2-6 haloalkenyl group, C _2-6 alkynyl group, C _2-6 haloalkynyl group, C _{3 -6} Cycloalkyl C _1-6 alkyl group or C _3-6 halocycloalkyl C _1-6 alkyl group,
n indicates an integer from 0 to 2
X is, C _1-6 alkyl, C _1-6 haloalkyl group, C _3-6 cycloalkyl alkyl groups, C _2-6 alkenyl groups, C _2-6 alkynyl group, C _2-6 haloalkenyl, C _{2- 6} Haloalkynyl group, C _1-6 alkoxy group, C _1-6 haloalkoxy group, C _3-6 halocycloalkyl group, C _1-6 alkyloxycarbonyl group, C _1-6 alkoxymethyl group, formyl group, Indicates a halogen atom, cyano group or nitro group,
Y represents a hydrogen atom, a halogen atom, a C _1-6 alkyl group or a C _1-6 haloalkyl group.
R ⁶ and R ⁷ may be the same or different, hydrogen atom, C _1-6 alkyl group, C _1-6 haloalkyl group, cyano group, cyano C _1-6 alkyl group, C _2-6 alkenyl group, C. _2-6 alkynyl group, C _2-6 haloalkenyl group, C _2-6 haloalkynyl group, phenyl group optionally substituted with one or more with R ⁸ , C _1-3 alkylphenyl group (at this time, the phenyl group is Indicates a C _3-6 cycloalkyl group which may be substituted at least one with R ⁹ ) or at least one with R ¹⁰ .
R ⁸ represents a halogen atom, C _1-6 alkyl group or C _1-6 haloalkyl group.
R ⁹ represents a halogen atom, C _1-6 alkyl group or C _1-6 haloalkyl group.
R ¹⁰ represents a halogen atom, a C _1-6 alkyl group or a C _1-6 haloalkyl group. ].

The compound of the present invention exerts an excellent effect as an agricultural and horticultural agent, particularly as an agricultural and horticultural pest control agent, a mite control agent, a nematode control agent or a disease control agent. It is also effective against pests that parasitize pet animals such as dogs and cats, and livestock such as cows and sheep.

In the definition of the compound of the present invention represented by the formula (1) or (2), the "halogen atom" means a chlorine atom, a bromine atom, an iodine atom or a fluorine atom, and is a "C _1-6 alkyl group". For example, methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, s-butyl group, t-butyl group, n-pentyl group, isopentyl group, neopentyl. It represents a linear or branched alkyl group having 1 to 6 carbon atoms, preferably 1 to 3 carbon atoms such as a group, a tert-pentyl group, an n-hexyl group, and an isohexyl group, and "C _1-6 haloalkyl". "" Indicates a linear or branched alkyl group having 1 to 6 carbon atoms substituted with one or more halogen atoms which may be the same or different, and "C _3-6 cycloalkyl" is , For example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc., which have 3 to 6 cyclic carbon atoms, preferably 3 to 4 cycloalkyl groups.

Examples of the C _1-6 haloalkyl group include fluoromethyl group, chloromethyl group, difluoromethyl group, trifluoromethyl group, chlorodifluoromethyl group, bromodifluoromethyl group, dichlorofluoromethyl group, 1-fluoroethyl group and 2 -Fluoroethyl group, 2-chloroethyl group, 2-bromoethyl group, 2-iodoethyl group, 2,2,2-trifluoroethyl group, 2,2,2-trichloroethyl group, pentafluoroethyl group, 2,2- Difluoroethyl group, 1-fluoroisopropyl group, 3-fluoropropyl group, 3-chloropropyl group, 3-bromopropyl group, heptafluoropropyl group, heptafluoroisopropyl group, 4-fluorobutyl group, 4-chlorobutyl, nonafluorobutyl Examples thereof include a linear or branched alkyl group having 1 to 6 carbon atoms substituted with 1 to 9 groups, preferably 3 to 9 halogen atoms.
Examples of the C _2-6 alkenyl group include vinyl group, allyl group, isopropenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-pentenyl group and 3-pentenyl group. 4-Pentenyl group, 1,1-dimethyl-2-propenyl group, 1-ethyl-2-propenyl group, 1-methyl-2-butenyl group, 1-methyl-3-butenyl group, 2-hexenyl group, 3- Number of carbon atoms having at least one double bond at any position such as hexenyl group, 4-hexenyl group, 5-hexenyl group, 1,1-dimethyl-2-butenyl group, 1,1-dimethyl-3-butenyl group, etc. Examples thereof include 2 to 6, preferably 2 to 4 linear or branched alkenyl groups.
Examples of the C _2-6 haloalkenyl group include 1-fluorovinyl group, 2-fluorovinyl group, 2,2-difluorovinyl group, 3-chloro-2-propenyl group, 3,3-difluoro-2-allyl group, and the like. 3,3-Dichloro-2-allyl group, 4,4,4-trifluoro-2-butenyl group, 4,4,4-trifluoro-3-butenyl group, 5-chloro-3-pentenyl group, 6- Linear with 2 to 6 carbon atoms substituted with 1 to 9, preferably 2 to 5 halogen atoms having at least one double bond at any position, such as a fluoro-2-hexenyl group. Alternatively, a branched chain alkenyl group can be mentioned.

Examples of the C _2-6 alkynyl group include an ethynyl group, a 2-propynyl group, a 1-methyl-2-propynyl group, a 1,1-dimethyl-2-propynyl group, a 1-butynyl group, a 2-butynyl group, and 3 -Butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 1-methyl-3-butynyl group, 1,1-dimethyl-2- 2 to 6 carbon atoms having at least one triple bond at any position such as butynyl group, 1,1-dimethyl-3-butynyl group, 1-methyl-3-pentynyl group, 1-methyl-4-pentynyl group, etc. , Preferably 2-3 linear or branched alkynyl groups.
C _2-6 haloalkynyl groups include fluoroethynyl group, 4,4,4-trifluoro-2-butynyl group, 5,5,5-trifluoro-3-pentynyl group, 1-methyl-3,3, 1-9, preferably 2-5, having at least one triple bond at any position, such as a 3-trifluoro-2-butynyl group, a 1-methyl-5,5,5-trifluoro-2-pentynyl group, etc. Examples thereof include a linear or branched alkynyl group having 2 to 6 carbon atoms substituted with one halogen atom.
Examples of the C _1-6 alkoxy group include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxy group, a tert-butoxy group, an n-pentoxy group and an n-hexyloxy group. Examples thereof include a linear or branched alkoxy group having 1 to 6 carbon atoms, preferably 1 to 3 carbon atoms such as a group.

Examples of the C _1-6 haloalkoxy group include fluoromethoxy group, dichloromethoxy group, trichloromethoxy group, difluoromethoxy group, trifluoromethoxy group, chlorodifluoromethoxy group, bromodifluoromethoxy group, dichlorofluoromethoxy group, 1-. Fluoroethoxy group, 2-fluoroethoxy group, 2-chloroethoxy group, 2-bromoethoxy group, 2-iodoethoxy group, 2,2,2-trifluoroethoxy group, 2,2,2-trichloroethoxy group, penta Fluoroethoxy group, 1-fluoroisopropoxy group, 3-fluoropropoxy group, 3-chloropropoxy group, 3-bromopropoxy group, 4-fluorobutoxy group, 4-chlorobutoxy group, etc., preferably 1 to 9 groups. Examples thereof include linear or branched alkoxy groups having 1 to 6 carbon atoms substituted with the halogen atom of.
Examples of the C _3-6 halocycloalkyl group include 1-fluorocyclopropyl, 2-fluorocyclopropyl, 2,2-difluorocyclopropyl, 2,2,3,3-tetrafluorocyclopropyl and 1-chlorocyclo. Propyl, 2-chlorocyclopropyl, 2,2-dichlorocyclopropyl, 2,2,3,3-tetrachlorocyclopropyl, 2,2-dibromocyclopropyl, 1-fluorocyclobutyl, 2-fluorocyclobutyl, 3 -Fluorocyclobutyl, 3,3-difluorocyclobutyl, 3,3-dichlorocyclobutyl, 1-fluorocyclopentyl, 2-fluorocyclopentyl, 3-fluorocyclopentyl, 2,2-difluorocyclopentyl, 3,3-difluorocyclopentyl, Examples thereof include cycloalkyl groups having 3 to 6 carbon atoms, preferably substituted with 1 to 4 halogen atoms, such as 2,2-dichlorocyclopentyl and 1-fluorocyclohexyl groups.

C _3-6 Cycloalkyl C _1-6 alkyl groups include, for example, cyclopropylmethyl, 2-cyclopropylethyl, 3-cyclopropylpropyl, 4-cyclopropylbutyl, 5-cyclopropylpentyl, 6-cyclopropylhexyl. , Cyclobutylmethyl, cyclopentylmethyl and the like. C _3-6 preferable number of carbon atoms of the C _3-6 cycloalkyl group and C _1-6 alkyl group constituting the cycloalkyl C _1-6 alkyl group are the same as those defined above.
C _3-6 halocycloalkyl C _1-6 alkyl groups include, for example, 1-fluorocyclopropylmethyl, 2-fluorocyclopropylmethyl, 2,2-difluorocyclopropylmethyl, 2-chlorocyclopropylmethyl, 2, 2-Dichlorocyclopropylmethyl, 2- (2,2-difluorocyclopropyl) ethyl, 2- (2,2-dichlorocyclopropyl) ethyl, 3- (2,2-difluorocyclopropyl) propyl, 4- (2) , 2-difluorocyclopropyl) butyl, 5- (2,2-dichlorocyclopropyl) pentyl, 6- (2,2-difluorocyclopropyl) hexyl, 2,2-difluorocyclobutylmethyl, 2,2-dichlorocyclo Examples thereof include groups such as butylmethyl, 3,3-difluorocyclopentylmethyl, 3,3-dichlorocyclopentylmethyl, 4,4-difluorocyclohexylmethyl or 4,4-dichlorocyclohexylmethyl. C _3-6 number of halogen atoms of C _3-6 halocycloalkyl group constituting halocycloalkyl C _1-6 alkyl group, and C _3-6 preferable number of carbon atoms of the halocycloalkyl group and a C _1-6 alkyl group Is as described above.

Examples of the C _1-6 alkoxycarbonyl group include groups such as methoxycarbonyl, ethoxycarbonyl, n-propylcarbonyl, n-butylcarbonyl, n-pentylcarbonyl, n-hexylcarbonyl and i-propylcarbonyl groups. The preferred number of carbon atoms of the C _1-6 alkoxy group constituting the C _1-6 alkoxycarbonyl group is as previously described.
The contents of the C _1-6 alkoxy group in C _1-6 alkoxymethyl group is as described above.
The contents of the C _1-6 alkyl group in the C _1-6 alkyl carbonyl group are as described above.
The contents of C _1-6 haloalkyl groups in C _1-6 haloalkylcarbonyl group is as described above.
The contents of the C _1-6 alkyl group in the C _1-6 alkyl sulfonyl group are as described above.
The contents of C _1-6 haloalkyl groups in C _1-6 haloalkylsulfonyl group is as described above.

Examples of the salt of the 1-benzylamine derivative represented by the formula (1) or (2) of the present invention include inorganic acid salts such as hydrochlorides, sulfates, nitrates and phosphates, acetates and fumarates. , Maleate, oxalate, methanesulfonate, benzenesulfonate, p-toluenesulfonate and other organic acid salts can be exemplified.
The 1-benzylamine derivative represented by the above formula (1) or (2) of the present invention may contain one or more asymmetric centers in its structural formula, and two or more kinds of optical isomers may be contained. And diastereomers may be present, and the present invention also includes all optical isomers and mixtures containing them in arbitrary proportions. Further, the 1-benzylamine derivative represented by the above formula (1) or (2) of the present invention may have two kinds of geometric isomers derived from a carbon-carbon double bond in its structural formula. However, the present invention also includes all geometric isomers and mixtures containing them in arbitrary proportions.

Hereinafter, typical methods for producing the novel 1-benzylamine derivative represented by the above formula (1) or (2) of the present invention will be shown, but the present invention is not limited thereto.
Reaction equation 1

[In the equation, X, Y and R ¹ are as defined in the equation (1). ]
In the method represented by the reaction formula 1, the 3-sulfinylbenzaldehyde derivative represented by the above formula (9) can be produced by the oxidation reaction of the 3-sulfanylbenzaldehyde derivative represented by the above formula (8).

As the solvent used in the oxidation reaction of the 3-sulfanylbenzaldehyde compound represented by the formula (8), a solvent inert to the reaction can be widely used. For example, aliphatic or alicyclic hydrocarbon solvents such as hexane, cyclohexane and heptane, aromatic hydrocarbon solvents such as benzene, chlorobenzene, toluene and xylene, halogenation of methylene chloride, 1,2-dichloroethane and chloroform. Hydrocarbon solvents, alcohol solvents such as methanol and ethanol, ester solvents such as methyl acetate and ethyl acetate, ketone solvents such as acetone and methyl ethyl ketone, amide solvents such as N, N-dimethylformamide, acetonitrile and propio. Examples thereof include nitrile solvents such as nitrile, aprotonic polar solvents such as N-methylpyrrolidone, N, N'-dimethylimidazolinone, carboxylic acids such as acetic acid, and water. One of these solvents can be used alone, or two or more of these solvents can be mixed and used as required.
Examples of the oxidizing agent used in the oxidation reaction of the 3-sulfanylbenzaldehyde compound represented by the formula (8) include m-chloroperbenzoic acid, sodium periodate, hydrogen peroxide, and tert-hypochlorite. Examples include butyl and sodium hypochlorite.
Such an oxidizing agent can be used in an amount usually 1 to 3 equivalents, preferably 1 to 2.5 equivalents, relative to the 3-sulfanylbenzaldehyde derivative represented by the above formula (8).
The reaction can usually be carried out in the range from −78 ° C. to the boiling point temperature of the solvent used, and it is preferable to carry out the reaction at 0 ° C. to room temperature.
The reaction time varies depending on the reaction temperature and the like and cannot be unequivocally determined, but the reaction is usually completed in about 0.5 to 24 hours.
The target compound obtained in each of the above reactions can be easily isolated from the reaction mixture by a commonly used isolation means, for example, an organic solvent extraction method, a chromatography method, a recrystallization method, a distillation method or the like. Further, it can be purified by ordinary purification means.

The 3-sulfanylbenzaldehyde derivative represented by the formula (8) used in the above reaction can be produced, for example, by the method described in Patent Document 2.
It can also be produced by a method described in known literature, for example, Molecules. 2015, 20, 5409-5422.

Reaction equation 2

[In the equation, X, Y, n, R ¹ , R ^2a , R ^2b , R ^2c , R ^2d , M, J ¹ and J ² are as defined in the equation (1). ]
In the reaction represented by the reaction formula 2, the 1-benzylamine derivative represented by the formula (1) is a benzaldehyde derivative represented by the formula (4) and an amine represented by the formula (5). , Can be produced by reacting in an inert solvent in the presence of a reducing agent.

As the solvent used in the reaction between the compound of the formula (4) and the compound of the formula (5), a solvent inert to the reaction can be widely used. For example, aliphatic or alicyclic hydrocarbon solvents such as hexane, cyclohexane and heptane, aromatic hydrocarbon solvents such as benzene, chlorobenzene, toluene and xylene, halogenation of methylene chloride, 1,2-dichloroethane and chloroform. Carbide-based solvent, ether-based solvent such as diethyl ether, tetrahydrofuran, 1,4-dioxane, ester-based solvent such as methyl acetate and ethyl acetate, alcohol-based solvent such as methanol, ethanol, propanol and isopropanol, acetic acid, formic acid and propion. Carboxylic acid solvent such as acid, amide solvent such as N, N-dimethylformamide, nitrile solvent such as acetonitrile and propionitrile, aprotonic polar solvent such as N-methylpyrrolidone and N, N'-dimethylimidazolinone. Etc. can be mentioned. One of these solvents can be used alone, or two or more of these solvents can be mixed and used as required. In particular, it is preferable to use a mixture of a small amount of acetic acid and another inert solvent.
As the reducing agent used in the reaction between the compound of the formula (4) and the compound of the formula (5), a known boron hydride compound and a salt thereof, or an aluminum hydride compound can be used. Examples of the boron hydride compound and a salt thereof include borane, borane-tetrahydrofuran complex, borane-2-methylpyridine complex, sodium borohydride, sodium cyanoborohydride, sodium triacetoxyborohydride and the like. Examples of the aluminum hydride compound include lithium aluminum hydride and diisopyrropyrua hydride.
Such a reducing agent can be used in an amount usually 1 to 100 equivalents, preferably 1 to 2 equivalents, relative to the benzaldehyde compound represented by the formula (4).
Regarding the ratio of the benzaldehyde compound represented by the formula (4) to the amines represented by the formula (5), it is more preferable to use 1 to 2 mol of (5) with respect to (4).
The reaction can usually be carried out in the range from −78 ° C. to the boiling point temperature of the solvent used, and it is preferable to carry out the reaction at room temperature to 100 ° C.
The reaction time varies depending on the reaction temperature and the like and cannot be unequivocally determined, but the reaction is usually completed in about 0.5 to 24 hours.
The target compound obtained in each of the above reactions can be easily isolated from the reaction mixture by a commonly used isolation means, for example, an organic solvent extraction method, a chromatography method, a recrystallization method, a distillation method or the like. Further, it can be purified by ordinary purification means.

Reaction equation 3

[In the equation, X, Y, n, R ¹ , R ⁶ and R ⁷ are as defined in the equation (2). ]
In the reaction represented by the reaction formula 3, the 1-benzylamine derivative represented by the formula (2) is the benzaldehyde derivative represented by the formula (4) and the amines represented by the formula (6). Can be produced by reacting in an inert solvent in the presence of a reducing agent.

As the solvent used in the reaction between the compound of the formula (4) and the compound of the formula (6), a solvent inert to the reaction can be widely used. For example, aliphatic or alicyclic hydrocarbon solvents such as hexane, cyclohexane and heptane, aromatic hydrocarbon solvents such as benzene, chlorobenzene, toluene and xylene, halogenation of methylene chloride, 1,2-dichloroethane and chloroform. Carbide-based solvent, ether-based solvent such as diethyl ether, tetrahydrofuran, 1,4-dioxane, ester-based solvent such as methyl acetate and ethyl acetate, alcohol-based solvent such as methanol, ethanol, propanol and isopropanol, acetic acid, formic acid and propion. Carboxylic acid solvent such as acid, amide solvent such as N, N-dimethylformamide, nitrile solvent such as acetonitrile and propionitrile, aprotonic polar solvent such as N-methylpyrrolidone and N, N'-dimethylimidazolinone. Etc. can be mentioned. One of these solvents can be used alone, or two or more of these solvents can be mixed and used as required. In particular, it is preferable to use a mixture of a small amount of acetic acid and another inert solvent.
As the reducing agent used in the reaction between the compound of the formula (4) and the compound of the formula (6), a known boron hydride compound and a salt thereof, or an aluminum hydride compound can be used. Examples of the boron hydride compound and a salt thereof include borane, borane-tetrahydrofuran complex, borane-2-methylpyridine complex, sodium borohydride, sodium cyanoborohydride, sodium triacetoxyborohydride and the like. Examples of the aluminum hydride compound include lithium aluminum hydride and diisopyrropyrua hydride.
Such a reducing agent can be used in an amount usually 1 to 100 equivalents, preferably 1 to 2 equivalents, relative to the benzaldehyde compound represented by the formula (4).
The ratio of the benzaldehyde compound represented by the formula (4) to the amines represented by the formula (6) is 1 to 2 mol of the compound of the formula (6) with respect to the compound of the formula (4). It is more preferable to use.
The reaction can usually be carried out in the range from −78 ° C. to the boiling point temperature of the solvent used, and it is preferable to carry out the reaction at room temperature to 100 ° C.
The reaction time varies depending on the reaction temperature and the like and cannot be unequivocally determined, but the reaction is usually completed in about 0.5 to 24 hours.
The target compound obtained in each of the above reactions can be easily isolated from the reaction mixture by a commonly used isolation means, for example, an organic solvent extraction method, a chromatography method, a recrystallization method, a distillation method or the like. Further, it can be purified by ordinary purification means.

Reaction equation 4

[During the ceremony,
R ¹ is C _1-6 alkyl group, C _1-6 haloalkyl group, C _2-6 alkenyl group, C _2-6 haloalkenyl group, C _2-6 alkynyl group, C _2-6 haloalkynyl group, C _{3 -6} Cycloalkyl C _1-6 alkyl group or C _3-6 halocycloalkyl C _1-6 alkyl group,
n indicates an integer from 0 to 2
X is, C _1-6 alkyl, C _1-6 haloalkyl group, C _3-6 cycloalkyl alkyl groups, C _2-6 alkenyl groups, C _2-6 alkynyl group, C _2-6 haloalkenyl, C _{2- 6} Haloalkynyl group, C _1-6 alkoxy group, C _1-6 haloalkoxy group, C _3-6 halocycloalkyl group, C _1-6 alkoxycarbonyl group, C _1-6 alkoxymethyl group, formyl group, halogen atom , Cyano group or nitro group,
Y represents a hydrogen atom, a halogen atom, a C _1-6 alkyl group or a C _1-6 haloalkyl group. ]
In the reaction represented by the reaction formula 4, the 1-benzyl alcohol derivative represented by the formula (3) is the benzaldehyde derivative represented by the formula (4) and NaBH ₄ , NaBH (OAc) ₃ or NaBH ₃ CN. Can be produced by reacting with and in an inert solvent.

As the solvent used in the reaction of the compound of the formula (4) with NaBH ₄ , NaBH (OAc) ₃ or NaBH ₃ CN, a solvent inert to the reaction can be widely used. For example, aliphatic or alicyclic hydrocarbon solvents such as hexane, cyclohexane and heptane, aromatic hydrocarbon solvents such as benzene, chlorobenzene, toluene and xylene, halogenation of methylene chloride, 1,2-dichloroethane and chloroform. Carbide-based solvents, ether-based solvents such as diethyl ether, tetrahydrofuran, 1,4-dioxane, ester-based solvents such as methyl acetate and ethyl acetate, alcohol-based solvents such as methanol, ethanol, propanol and isopropanol, acetic acid, formic acid and propion. Carboxylic acid solvent such as acid, amide solvent such as N, N-dimethylformamide, nitrile solvent such as acetonitrile and propionitrile, aprotonic polar solvent such as N-methylpyrrolidone and N, N'-dimethylimidazolinone. Etc. can be mentioned. One of these solvents can be used alone, or two or more of these solvents can be mixed and used as required.
The NaBH ₄ , NaBH (OAc) ₃ or NaBH ₃ CN used in the reaction is usually 1 to 100 equivalents, preferably 1 to 2 equivalents, relative to the benzaldehyde compound represented by the above formula (3). Can be used in quantity.
The reaction can usually be carried out in the range from −78 ° C. to the boiling point temperature of the solvent used, and it is preferable to carry out the reaction at room temperature to 100 ° C.
The reaction time varies depending on the reaction temperature and the like and cannot be unequivocally determined, but the reaction is usually completed in about 0.5 to 24 hours.
The target compound obtained in each of the above reactions can be easily isolated from the reaction mixture by a commonly used isolation means, for example, an organic solvent extraction method, a chromatography method, a recrystallization method, a distillation method or the like. Further, it can be purified by ordinary purification means.

Reaction equation 5

[In the formula, X, Y, n, R ¹ , R ^2a , R ^2b , R ^2c , R ^2d , M, J ¹ and J ² are as defined in formula (1), and Z is methanesulfonyl. Indicates a group or a trifluoromethanesulfonyl group. ]
In the reaction represented by the reaction formula 5, the compound represented by the formula (7) is a benzyl alcohol derivative represented by the formula (3) and methanesulfonyl chloride or trifluoromethanesulfonyl chloride, which is a base such as triethylamine. It can be produced by reacting in the presence of an inert solvent such as dichloromethane.
Further, the benzylamine derivative represented by the formula (1) is prepared by combining the compound represented by the formula (7) and the amines represented by the formula (5) in an inert solvent in the presence of an appropriate base. It can be produced by reacting with.

As the solvent used in the reaction between the compound of the formula (7) and the compound of the formula (5), a solvent inert to the reaction can be widely used. For example, aliphatic or alicyclic hydrocarbon solvents such as hexane, cyclohexane and heptane, aromatic hydrocarbon solvents such as benzene, chlorobenzene, toluene and xylene, halogenation of methylene chloride, 1,2-dichloroethane and chloroform. Carbide-based solvent, ether-based solvent such as diethyl ether, tetrahydrofuran, 1,4-dioxane, ester-based solvent such as methyl acetate and ethyl acetate, alcohol-based solvent such as methanol, ethanol, propanol and isopropanol, acetic acid, formic acid and propion. Carboxylic acid solvent such as acid, amide solvent such as N, N-dimethylformamide, nitrile solvent such as acetonitrile and propionitrile, aprotonic polar solvent such as N-methylpyrrolidone and N, N'-dimethylimidazolinone. Etc. can be mentioned. One of these solvents can be used alone, or two or more of these solvents can be mixed and used as required.
Examples of the base used in the reaction between the compound represented by the formula (7) and the amines represented by the formula (5) include potassium carbonate, cesium carbonate, oily sodium hydride, sodium hydroxide, and the like. Triethylamine and the like are preferable.
The ratio of bases used in the reaction between the compound represented by the formula (7) and the amines represented by the formula (5) is 1 to 2 times that of the compound represented by the formula (7). It is more preferable to use a molar amount.
The reaction can usually be carried out in the range from −78 ° C. to the boiling point temperature of the solvent used, and it is preferable to carry out the reaction at room temperature to 100 ° C.
The reaction time varies depending on the reaction temperature and the like and cannot be unequivocally determined, but the reaction is usually completed in about 0.5 to 24 hours.
The target compound obtained in each of the above reactions can be easily isolated from the reaction mixture by a commonly used isolation means, for example, an organic solvent extraction method, a chromatography method, a recrystallization method, a distillation method or the like. Further, it can be purified by ordinary purification means.

Reaction equation 6

[In the formula, X, Y, n, R ¹ , R ⁶ and R ⁷ are as defined in the formula (2), and Z represents a methanesulfonyl group or a trifluoromethanesulfonyl group. ]
In the reaction represented by the reaction formula 6, the compound represented by the formula (7) is a benzyl alcohol derivative represented by the formula (3) and a base such as triethylamine and methanesulfonyl chloride or trifluoromethanesulfonyl chloride. It can be produced by reacting in an inert solvent such as dichloromethane in the presence of.
Further, the 1-benzylamine derivative represented by the formula (2) inactivates the compound represented by the formula (7) and the amines represented by the formula (6) in the presence of an appropriate base. It can be produced by reacting in a solvent.

As the solvent used in the reaction between the compound of the formula (7) and the compound of the formula (6), a solvent inert to the reaction can be widely used. For example, aliphatic or alicyclic hydrocarbon solvents such as hexane, cyclohexane and heptane, aromatic hydrocarbon solvents such as benzene, chlorobenzene, toluene and xylene, halogenation of methylene chloride, 1,2-dichloroethane and chloroform. Carbide-based solvent, ether-based solvent such as diethyl ether, tetrahydrofuran, 1,4-dioxane, ester-based solvent such as methyl acetate and ethyl acetate, alcohol-based solvent such as methanol, ethanol, propanol and isopropanol, acetic acid, formic acid and propion. Carboxylic acid solvent such as acid, amide solvent such as N, N-dimethylformamide, nitrile solvent such as acetonitrile and propionitrile, aprotonic polar solvent such as N-methylpyrrolidone and N, N'-dimethylimidazolinone. Etc. can be mentioned. One of these solvents can be used alone, or two or more of these solvents can be mixed and used as required.
Examples of the base used in the reaction between the compound represented by the formula (7) and the amines represented by the formula (6) include potassium carbonate, cesium carbonate, oily sodium hydride, sodium hydroxide or. Triethylamine and the like are preferable.
The ratio of the base used in the reaction between the compound represented by the formula (7) and the amines represented by the formula (6) is 1 to 2 times the molar amount of the base compared to the compound of the formula (7). It is more preferable to use the amount.
The reaction can usually be carried out in the range from −78 ° C. to the boiling point temperature of the solvent used, and it is preferable to carry out the reaction at room temperature to 100 ° C.
The reaction time varies depending on the reaction temperature and the like and cannot be unequivocally determined, but the reaction is usually completed in about 0.5 to 24 hours.
The target compound obtained in each of the above reactions can be easily isolated from the reaction mixture by a commonly used isolation means, for example, an organic solvent extraction method, a chromatography method, a recrystallization method, a distillation method or the like. Further, it can be purified by ordinary purification means.

Representative compounds of the 1-benzylamine derivatives represented by the formulas (1) and (2) are exemplified in Tables 1 to 4, but the present invention is not limited thereto. In the table, the physical properties indicate the properties and the melting point (° C.), "n-" indicates normal, "s-" indicates secondary, "t-" indicates tertiary, and "i-" indicates iso. "Me" indicates a methyl group, "Et" indicates an ethyl group, "Pr" indicates a propyl group, "Bu" indicates a butyl group, and "Ph" indicates a phenyl group.

General formula (1)

table 1

Table 2

Table 3

General formula (2)

Table 4

Typical compounds of 1-benzyl alcohols represented by the above formula (3) are illustrated in Table 5, but the present invention is not limited thereto.
The physical properties in the table indicate the properties and the melting point (° C.), where "n-" indicates a normal, "Me" indicates a methyl group, and "Pr" indicates a propyl group.

General formula (3)

Table 5

Typical compounds of benzaldehydes represented by the above formula (4) are illustrated in Table 6, but the present invention is not limited thereto.
The physical properties in the table indicate the properties and the melting point (° C.), where "n-" indicates a normal, "Me" indicates a methyl group, and "Pr" indicates a propyl group.

General formula (4)

The compounds of the present invention can be used in agriculture, indoors or in forests for the prevention and extermination of organisms that are harmful to livestock or in various situations such as hygiene. Specific usage situations, target pests, and usage methods are shown below, but the content of the present invention is not limited thereto.
The compounds of the present invention include agricultural crops, for example, edible crops (wheat such as rice, barley, wheat, rye, oat, corn, potatoes, sweet potatoes, satoimo, soybeans, red beans, sora beans, red beans, green beans, peanuts, etc. Beans, etc.), vegetables (cabbage, white vegetables, radish, buds, broccoli, cauliflower, komatsuna and other Abrana crops, pumpkin, cucumber, squid, makuwauri, melon and other crops, eggplant, tomato, pepper, pepper , Okura, spinach, lettuce, brick, carrot, gobo, garlic, onion, onion, etc.), mushrooms (shitake, mushroom, etc.), fruit trees / fruits (apple, citrus, pear, grape, peach, plum) , Cherry blossoms, walnuts, chestnuts, almonds, bananas, strawberries, etc.), fragrances, etc. Appreciation crops (lavender, rosemary, thyme, parsley, pepper, ginger, etc.), special crops (tobacco, tea, beans, sugar cane, hops, etc.) Cotton, hemp, olive, rubber, coffee, etc.), grass and feed crops (timothy, clover, alfalfa, corn, sorghum, orchardgrass, rice grass, bean grass, etc.), turf (Koryo turf, bentgrass, etc.) ), Forest trees (beans, beans, pine, hiba, cedar, cypress, etc.) and ornamental plants (herbs and flowers such as kiku, roses, carnations, orchids, garden trees such as ginkgo, cherry blossoms, aoki, etc.) It can also be used to control arthropods, soft animals, nematodes, and fungi such as fungi, deformed fungi, fungi, and exsanguins, as well as harmful organisms such as bacteria. .. Specific pests include the following.

Lepidoptera of the phylum Arthropod, for example, Cossidae Helicoverpa armigera, Heliothis spp., Agrotis segetum, Autographa nigrisigna, Tricho ), Yotoga (Mamestra brassicae), Shiroichimojiyoto (Spodoptera exigua), Hasmonyoto (Spodoptera litura), etc., Suga family Konaga (Plutella xylostella), Hamakiga family apple cossidae (Adoxophyes) honmai), Midarekakumonhamaki (Archips fuscocupreanus), Chahamaki (Homona magnanima), Chanohosoga (Caloptilia theivora), Nashihimeshinkui (Grapholita molesta), etc., Chaminoga (Eumeta minuscula), etc. malinella), peach hamoguriga (Lyonetia clerkella), etc., cossidae citrus hamogriga (Phyllocnistis citrella), etc., cossidae kinmon hosoga (Phyllonorycter ringoniella), etc. , Lepidoptera (Stathmopoda masinissa), etc., Lepidoptera (Pectinophora gossypiella), Lepidoptera (Carposina niponensis), Cossidae (Cossidae), Cossidae (Cossus jezoensis), etc. , Iraga family Iraga (Monemaflavecens), Hirohelia oila (Parasa lepida), Himekuroiraga (Scopelodes con) Tracus, etc., Crambi suppressalis, Scirpophaga incertulas, Cnaphalocrocis medinalis, Helulla undalis, Conogethes punctiferis, Conogethes punctiferlis, etc. Shibatuga (Parapediasia teterrella), etc., Tosakaftomeiga (Locastra muscosalis), etc.

Ichimonjiseri (Parnara guttata) of the family Lappet moth, Namiageha (Papilio xuthus) of the swallowtail family, Piieris rapae crucivora, etc. of the white butterfly family, Uranamishijimi (Lampides boeticus), etc. Etc., Convolvulus hawk (Agrius convolvuli), etc., Monkuroshachihoko (Phalera flavescens), etc., Lappet moth family, Obikareha (Malacosoma neusttrium testaceum), etc., Yamamayuga family, Kussan (Saturnia japonica), etc. (Euproctis pseudoconspersa) Himeshiromondokuga (Orgyia thyellina), Akamondokuga (Telochurus recens approximans), etc., Kwagomadara Hitori (Spilosoma imparilis), American Shirohitori (Hyphantria cunea), etc. Adults, larvae and eggs such as pomonella);

Coleoptera, for example, Coleoptera (Anomala cuprea), Chrysomelidae (Popillia japonica), Oxycetonia jucunda, Chrysomelidae (Anomala geniculata), etc., Jewel beetle (Anomala geniculata), etc. , Beetle beetle, Melanotus fortnumi, etc., Epilachna vigintioctopunctata, etc., Chrysomelidae, Anoplophora malasiaca, Chrysomelidae, Chrysomelidae, Chrysomelidae, Chrysomelidae, Chrysomelidae, Chrysomelidae, Chrysomelidae, Chrysomelidae Aulacophora femoralis), root worm species (Diabrotica spp.), Chrysomelidae (Phyllotreta striolata), longhorn beetle (Cassida nebulosa), jewel beetle (Phaedon brisicae), rice leaf beetle (Oulema lyzae), rice leaf beetle (Oulema) ), Etc., Chrysomelidae (Rhynchites heros), etc., Chrysomelidae (Cylas formicarius), etc., Chrysomelidae (Curculio sikkimensis), Chrysomelidae (Curculio sikkimensis), Jewel beetle (Lissorhoptrus) Adults, larvae and eggs of the family Coleoptera, Epuraea domina, such as grandis) and Sphenophrus venatus vestitus;

Hemiptera stink bugs (Heteroptera), for example, stink bugs (Eurydema rugosum), stink bugs (Eysarcoris lewisi), stink bugs (Eysarcoris parvus), stink bugs (Eysarcoris parvus), stink bugs (Eysarcoris parvus), stink bugs (Eysarcoris parvus) Stink bug (Plautia stali), stink bug (Halymorpha mista), stink bug (Urochela luteovoria), stink bug family stink bug (Togo hemipterus) stink bug (Togo hemipterus) stink bug (Togo hemipterus) stink bug , Stink bug (Cletus punctiger), stink bug (Leptocorisa chinansis), stink bug (Dysdeercus cingulatus), stink bug (Dysdeercus cingulatus), stink bug (Stephanitis stink bug), stink bug (Stephanitis) Etc., stink bugs (Apolygus spinolai), stink bugs (Stenotus rubrovittalus), stink bugs (Trigonotylus coelestialium), stink bugs, stink bugs (Megacopta punctatissim)

Homoptera of the order Hemiptera, for example, the whitefly (Platypleura kaempferi), the whitefly family Homoptera (Arboridia apicalis), the whitefly (Empoasca onukii), the whitefly (Empoasca onukii), the whitefly (Platypleura kaempferi), etc. , Whitefly Homoptera (Nephotettix virescens), etc., Delphacidae Himetobiunka (Laodelphax striatellus), Tobiirounka (Nilaparvata lugens), Sejirounka (Sogatella furcifera), etc., Psyllidae (Sogatella furcifera), etc., Psyllidae, Psyllidae, Psyllidae, Psyllidae, Psyllidae Various biotypes of whitefly (Diaphorina citri), Delphacidae whitefly (Aleurocanthus spiniferus), silver leaf whitefly (Bemisia argentifolii), tobacco whitefly (Bemisia tabaci), whitefly, whitefly (Dialeurodesci), etc. , Psyllidae whitefly (Viteus vitifolii), etc.

Aphis citricola, Aphis craccivora, Wata aphid (Aphis gossypii), Potato aphid (Aulacorthum solani), Daikon aphid (Brevicoryne brassicae), Aphid aphid (Brevicoryne brassicae), Aphid aphid (Aphis citricola), Aphid aphid (Aphis craccivora) (Toxoptera citricidus), Niwatokohigenaga aphid (Aulacorthum magnoliae), Nasia aphid (Schizaphis piricola), Nippolachnus aphid, Nisedaikon aphid (Lipaphis erysimi), Momokofuki aphid (Lipaphis erysimi) Pleotrichophorus chrysanthemi), Kikuhimehigenaga aphid (Macrosiphoniella sanborni), Soramamehigenaga aphid (Megoura crassicauda), Ibarahigenaga aphid (Sitobion ibarae), Tulip higenaga aphid (Macrosiphoniella) aphid (Macrosiphoniella) ), Okabonoaka aphid (Rhopalosiphum rufiabdominalis), wheat aphid (Rhopalosiphum padi), wheat aphid (Sitobion aphid), apple aphid (Eriosoma lanigerum), etc., Watafukikaigaramushi (Eriosoma lanigerum), etc. Aphids (Pseudococcus comstocki), Aphids (Phenacoccus viburnae), Fujikonakaigaram (Phenacoccus kraunhiae), Aphids of the family Aphids (Ceroplastes ceriferus), Aphids (Ceroplastes ceriferus) (Aonidiell Adults, larvae and eggs such as a aurantii), San Jose scale (Comstockaspis perniciosa), Pseudaulacaspis pentagoa, and Unaspis yanonensis;

Thrips (Thysanoptera), for example, Thrips palmi Karny (Scirtothrips dorsalis), Thrips palmi (Thrips palmi), Negia thrips (Thrips tabaci), Thrips tabaci, Thrips tabaci, Thrips thrips (Thrips) Thrips palmi Karny (Frankliniella occidentalis), Thrips palmi Karny (Heliothrips haemorrhoidalis), etc., Thrips palmi Karny (Ponticulothrips diospyrosi), Thrips palmi Karny (Haplothrips)

Hymenoptera, for example, Tenthredinidae (Athalia rosae ruficornis), Churenji bee (Arge pagana), Mifushihabachi (Arge mali), etc., Formica japonica (Dryocsmus kuriphilus) Adults such as the leaf-cutting bees (Megachile nipponica nipponica), Formica japonica, Camponotus kiusiuensis, Lasius fuliginosus, Fire ant (Solenopsis richteri, S. invicta, S. geminata) And eggs;
Diptera, for example, Agromyzidae, Agromyzidae, Agromyzidae, Agromyzidae, Rhacochlaena japonica, Bactrocera cucurbitae, etc., Agromyzidae, Agromyzidae, Agromyzidae, Agromyzidae, Agromyzidae, Agromyzidae, Agromyzidae, Agromyzidae Agromyzidae (Drosophila suzukii), etc., Agromyzidae (Liriomyza trifolii), Tomato leafminer (Liriomyza sativae), Agromyzidae (Chromatomyia horticola), Agromyzidae (Agromyza oryzae), Agromyzidae (Agromyza oryzae) Adults, larvae and eggs such as leafminer (Delia platura) and leafminer fly (Delia antiqua);

Orthoptera, for example, Migratory locust (Locusta migratoria), Ruspolia lineosa (Ruspolia lineosa), Teleogryllus emma (Teleogryllus emma), Oxya yezoensis (Truljalia hibinonis), etc. ) Etc., adults, larvae and eggs such as Oxya yezoensis of the Orthoptera family;
Adults, larvae and eggs of the order Termites (Isoptera), such as the termites Odontotermes formosanus of the family Termites;
Adults, larvae and eggs of the order Earwig (Dermaptera), such as the earwig (Labidura riparia) of the family Earwigidae;

Adults, larvae and eggs of the phylum Arthropod Collembola, such as the Collembola (Collembola), for example, the Collembola (Sminthurus viridis), the Isopodaceae, Onychiurus matsumotoi; Adults, larvae and eggs of the Collembola (Isopada), such as the pill bug (Armadillidium vulgare) of the pill bug family;
Acari of the phylum Spider Mite, for example, Polyphagotarsonemus latus, Phytonemus pallidus, Penthaleus major, etc., Brevipalpus mite of the family. lewisi, Brevipalpus phoenicis, etc., Panonychus citri, Panonychus ulmi, Tetranychus urticae, Tetranychus urticae, Tetranychus kanzawai, Tetranychus kanzawai, Oligonychus ununguis, Bryobia eharai, Eotetranychus kankitus, Bryobia praetiosa, etc., Aculus Schlechtendali, Aculus Schlechtendali, ), Fake mite (Eriophyes chibaensis), Tulip mite (Aceria tulipae), Grape hamogri mite (Colomerus vitis), Peach mite (Aculus fockeui), Chanosabi mite (Calacarus carinatus), etc. Adults, larvae and eggs such as robini);

Primitive string tongues of the molluscs Gastropods (Architaenioglossa), such as Pulmonata, such as Pomacea canaliculata of the family Tanishimodoki, Pulmonata, such as Achatina fulica of the family Acusta despectarum Namekuji (Meghimatium bilineatum), Niwakouranamekuji (Milax gagates), Keelback slug (Lehmannina valentiana), Giant African snail (Acusta despecta sieboldiana), etc.
Tylenchida of the phylum phylum, for example, Ditylenchus destructor of the Anguina family, Tylenchorhynchus claytoni of the Tylenchorhynchus, etc., Pratylenchus of the Platylencus family. ), Pratylenchus coffeae, etc., Helicotylenchus dihystera, etc., Heterodera rostochiensis, Globodera rostochiensis, etc., Meloid Guinea family Nematodes (Criconema jaejuense), etc., Strawberry nematodes (Nothotylenchus acris), etc., Aphelecchoides fragarriae, etc .; Aphelecchoides fragarriae, etc .; .), Yumihari nematode (Trichodorus sp.), Etc. of the family Trichodolus family;
Fungi and bacteria such as the phylum Eumycota, the phylum Dictyostelium (Myxomycota), the phylum Bacteriomycota, the phylum Actinomycota (Actinomycota).

Specific examples of diseases to which the compound of the present invention can be applied include rice blast (Pyricularia oryzae), sesame leaf blight (Cochliobolus miyabeanus), blight (Rhizoctonia solani), and internal scab (Pantoea ananatis). ), Brown streak disease (Acidovorax avene subsp. Avenae), leaf sheath browning disease (Pseudomonas fuscovaginae), white leaf blight (Xanthomonas oryzae pv. Oryzae), bacterial wilt disease (Burkholderia plantarii), etc.; wheat udonko disease (Erysiphe) graminis), Fusarium head blight (Gibberella zeae), Fusarium head blight (Puccinia striiformis, P. graminis, P. recondita, P. hordei), Snow rot (Typhula sp., Micronectriella nivalis), Naked scab (Ustilago tritici) . Nuda), Namagusa black spike disease (Tilletia caries), eye print disease (Pseudocercosporella herpotrichoides), cloud-shaped disease (Rhynchosporium secalis), leaf blight (Septoria tritici), blight (Leptosphaeria nodorum), net spot disease (Pyrenophora) , Hyomon disease (Helminthosporium zonatum Ikata), black scab (Pseudomonas syringae pv. Japonica), etc .; citrus black spot disease (Diaporthe citri), scab (Elsinoe fawcetti), fruit rot (Penicillium digitatum) , Brown rot (Phytophthora citrophthora ,, P. Nicotianae), scab (Phyllosticta citricarpa), etc .; Alternaria mali), scab (Venturia inaequalis), scab (M) ycospherella pomi), Colletotrichum acutatum, Botryosphaeria berengeriana, Gymnosporangium yamadae, Monilinia fructicola, etc .;

None scab (Venturia nashicola, V. pirina), scab (Alternaria kikuchiana), gymnosporangium haraeanum, ash (Monilinia fructigena), etc .; thigh scab (Monilinia fructicola), scab (monilinia fructicola) Cladosporium carpophilum, Phomopsis sp., Brenneria nigrifluens, etc .; Black grape disease (Elsinoe ampelina), Colletotrichum acutatum, Uncinula necator, rust Phakopsora ampelopsidis, Guignardia bidwellii, Plasmopara viticola, Monilinia fructigena, Cladosporium viticolum, Botrytis cinerea, root cancer bacillus disease (Agrobacterium vitis), etc .; Monilinia fructicum (Gloeosporium kaki), deciduous disease (Cercospora kaki, Mycoshaerella nawae), etc .; Monilinia fructicum (Colletotrichum lagenarium), Udonko disease (Sphaerotheca fuliginea, Oidiopsis) Blight (Didymella bryoniae), vine blight (Fusarium oxysporum), sticky disease (Pseudoperonospora cubensis), epidemic (Phytophthora sp.), Seedling blight (Pythium sp.), Etc.; Cucumber spot bacterial disease (Pseudomonas syringae) Lochrymans), Bacterial wilt disease (Pseudomonas viridiflava), Bacterial brown spot disease (Xanthomonas campestris pv. Cucurbitae), etc .; Bacterial disease of melon brown spot (Xanthomonas campestris pv. Disease (St reptomyces sp.) Etc.; Watermelon fruit spot bacterial disease (Acidovorax avenae pv. Citrulli) etc.;

Ralstonia solanacearum, etc. of eggplant family; tomato ring pattern disease (Alternaria solani), leaf mold disease (Cladosporium fullvum), plague (Phytophthora infestans), canker disease (Clavibacter michiganense subsp. Michiganense), stem stalk Diseases (Pseudomonas corrugata), soft rot (Pectobacterium carotovorum subsp. Carotovorum), etc .; brown spot disease (Phomopsis vexans), udonko disease (Erysiphe cichoracearum), etc.; black spot disease (Alternaria japonica), white spot disease of abrana family vegetables (Cercosporella brassicae) Soft rot (Pectobacterium carotovorum subsp. Carotovorum), etc .; Kyabetsu rot (Pseudomonas syringae pv. Marginalis), Black rot (Xanthomonas campestris pv. Campestris), etc.; Lettuce rot (Psudomonas campestris pv. Campestris); , Spot bacterial disease (Xanthomonas campestris pv. Vitians) Negi rust (Puccinia allii), etc .; Soybean purple spot disease (Cercospora kikuchii), Black spot disease (Elsinoe glycines), Black spot disease (Diaporthe phaseolorum var. Sojae), etc. Pectotrichum lindem thianum, etc .; Black astringent disease (Cercospora personata), Brown spot disease (Cercospora arachidicola), etc.; Erysiphe pisi, etc.; Summer epidemic of potato (Alternaria) solani), plague (Phytophthora infestans), leaf rot fungus (Rhizoctonia solani), etc .; strawberry udonko disease (Sphaerotheca humuli), etc .; Elsinoe leucospila), red burning disease (Pseudomonas syringae pv. Theae), canker disease (Xanthomonas campestris pv. Theicola), etc.;

Tobacco red spot disease (Alternaria longipes), pythium disease (Erysiphe cichoracearum), charcoal disease (Colletotrichum tabacum), sticky disease (Peronospora tabacina), plague (Phytophthora nicotianae), wilt disease (Ralstonia solanacearum) Pectobacterium carotovorum subsp. Carotovorum, etc .; Cercospora beticola, Aphanomyces cochliodes, etc .; Rose scab (Diplocarpon rosae), Udonko disease (Sphaerotheca pannosa), etc. Diseases (Septoria chrysanthemi-indici), white rust (Puccinia horiana), root cancer (Agrobacterium tumefaciens), etc .; Botrytis cinerea of various crops such as eggplant, cucumber and lettuce, mycorrhizal disease ( Sclerotinia sclerotiorum; turf snow rot (Pythium iwayamai, Tyohula incarnate, Fusarium nivale, Sclerotinia borealis), Udonko disease (Erysiphe graminis), Farrying disease (Lycoperdon perlatum, Lepista) (Ceratobasidium spp.), Bacterial wilt (Gaemannomyces graminis), Curvularia geniculata, Leaf rot (Rhizoctonia solani), Pythium periplocum, Pythium vanterpoolii, Puccinia sp. Spot disease (Sclerotinia homoeocarpa), etc .; Examples include bentgrass red burning disease (Pythium aphanidermatum) and charcoal disease (Colletotrichum sp.).

The compound of the present invention operates indoors in buildings including ordinary houses, and damages or rots wood and its processed products such as wooden furniture, stored foods, clothing, books, etc., and damages our lives. It can also be used to control arthropods and fungi. Specific pests include the following.

Termites of the phylum Termites, such as termites of the family Termites (Coptotermes formosanus), Yamato termites (Reticulitermes speratus), and other termites of the genus Reticulitermes hesperus, R. tibialis, R. flavipes, R. lucifugus, R. santonensis, etc.), American termites (Incisitermes minor), termites (Odontotermes formosanus), termites Hodotermopsis jzponica, termites and termites (Cryptotermes domesticus). egg;
Coleoptera, for example, Maize weevil (Sitophilus zeamais), Maize weevil (Sitophilus zeamais), Maize weevil (Callosobruchus chinensis), Pea weevil (Bruchus pisorum), Pea weevil (Bruchus pisorum) Maize weevil (Tribolium castaneum), Maize weevil (Tribolium confusum), etc., Maize weevil (Oryzaephilus surinamensis), Skin beetle (Cryptolestes pusillus), Cryptolestes pusillus, Maize weevil, La weevil (Stegobium paniceum), etc., Maize weevil (Attagenus unicolor japonicus), Himemaru weevil (Anthrenus verbasci), Harajiro weevil (Dermestes maculatus), etc., Maize weevil, Maize weevil, etc. Adults, larvae and eggs of the skin beetle Lyctus brunneus, such as the weevil Dinoderus minutus and the maize weevil (Rhizopertha dominica);

Chowidae, for example, Spodoptera frugiperda (Cadra cautella), Spodoptera frugiperda (Ephestia kuehniella), Indianmeal moth (Plodia interpunctella), Angoumois grain moth (Sitotroga cerealella) Adults, larvae and eggs of translucens, Tineola bisselliella, etc .; Adults, larvae and eggs of the order Moth, for example, Lepinotus reticulatus of the family Snout moth, Liposcelis bostrychophilus.
Adults, larvae and eggs of the order Cockroach, such as the cockroach (Blattella germanica), the cockroach (Periplaneta fuliginosa), the cockroach (Periplaneta japonica), and the cockroach (Blattella germanica); Adults, larvae and eggs such as pharaoni) and cockroaches (Monomorium nipponense);

Adults, larvae and eggs of the order Thysanura, such as Ctenolepisma villosa and Lepisma saccharina of the family Lepismatidae;
Adults, larvae and eggs of the order Flies, such as Drosophila melangogaster of the Drosophila family, Piophila casei of the Piophila family, etc.;
Adults, larvae and eggs of the order Arachnids of the phylum Arachnid, such as Tyrophagus putrescentiae of the family Acaridae, Lardoglyphus konoi, and Carpoglyphus lactis of the family Acaridae;
Tyromyces palustris, Coriolus versicolor, etc., which are wood-rotting fungi of fungi;
Deterioration of materials Microorganisms such as Aspergillus niger, Aspergillus terreus, Aureobasidium pullulans, Chaetomium globosum, Cladosporium cladosporioides, Eurotium tonophilus, Fusarium moniliforme, Gliocladium virens, Myrothecium verrucaria, Penicillium ci

The compound of the present invention can also be used to control harmful organisms that damage or weaken trees in natural forests, planted forests and urban green areas. Specific pests include the following.

Arthropod phylum Insectidae, for example, Sugidokuga (Calliteara argentata), Chadokuga (Euproctis pseudoconspersa), Himeshiromondokuga (Orygia recens approximans), Dokuga (Euproctis subflava), Maiga (Lymantria disp) Lackey moth (Malacosoma neustria testacea), Matsukareha (Dendrolimus spectabilis), Tsuga kareha (Dendrolimus superans), etc., Meiga family Crytoblabes loxiella, etc., Yaga family longhorn beetle (Agrotis se) (Ptycholoma lecheana circumclusana), Kurimiga (Cydia kurokoi), Sugikasaga (Cydia cryptomeriae), etc., Hitrigger family, Spilosoma imparilis, American white-spotted beetle (Hyphantria cunea), etc., Moguri-chibiga family, etc. Adults, larvae and eggs of Lackey moth (Parasa lepida), Lackey moth (Scopelodes contracus), Tenguiraga (Microleon longipalpis); Longhorn beetle, for example, Anomala rufocuprea, Nagachakogane (Anomala rufocuprea), Nagachakogane Family jewel beetle (Agrilus spininipennis), longhorn beetle family pine beetle (Monochamus alternatus), hamushi family sugihamushi (Basilepta pallidula), elephant family sabihyotanzoumushi (Scepticus squirrel) ), Etc., Sipalinus gigas, etc., Longhorn beetle (Tomicus piniperda), Longhorn beetle (Indocryphalu), etc. Adults, larvae and eggs of Rhyzopertha dominica, etc. of the family Rhyzopertha dominica, etc.

Hemiptera, for example, Cinara todocola of the Aphididae family, Adelges japonicus of the Aphididae family, Diaspididae Sugimarukaigaramushi (Aspidiotus cryptomeriae), etc. Adults, larvae and eggs such as ceriferus);
Adults, larvae and eggs of the order Tenthredinidae, such as the Tenthredinidae Pachynematus itoi, the Neodiprion sertifer of the family Tenthredinidae, and the Cecidomyiidae (Dryocosmus kuriohilus); Adults, larvae and eggs of the Crane fly (Tipula aino), Tenthredinidae (Strobilomyia laricicola), etc.
Adults, larvae and eggs of the arachnids of the phylum Arachnid, such as the ticks Oligonichus hondoensis and Abies sachalinensis (Oligonichus ununguis);
C. elegans Tyrenx, for example, Bursaphelenchus xylophilus of the family Parasitaferencus.

The compounds of the present invention are arthropods that parasitize vertebrates, especially warm-blooded vertebrates such as cows, sheep, goats, horses, pigs, poultry, dogs, cats and fish, internally or externally. It can also be used to prevent, treat or control animals, nematodes, trematodes, vertebrates and protozoa. In addition to the above, the target animal species include rodents such as mice, rats, hamsters and squirrels, carnivores such as ferrets, pets and experimental animals of birds such as ducks and pigeons. Specific pests include the following.

Flies of the phylum Psychodidae, such as Yamatoab (Tabanus rufidens), Akaushiab (Tabanus chrysurus), Blowfly (Musca bezzii), Psychodidae (Musca domestica), Stomoxys calcitrans, etc. Ceratopogonidae (Gasterophilus intestinalis), Ceratopogonidae (Hypoderma bovis), Botfly (Oestrus ovis), Blowfly (Aldrichina grahami), Ceratopogonidae (Ceratopogonidae) Etc., Botfly (Sepsis punctum), Psychodidae (Telmatoscopus albipunctatus), Blowfly (Psychoda alternata), Ceratopogonidae (Culex pipiens molestus), Ceratopogonidae (Culex piens molestus) , Sinahamadaraka (Anopheles sinensis), Kogataakaieka (Culex pipiens triaeniorhynchus summorosus), Botfly (Ades albopictus), etc. Adults, larvae and eggs such as Culicoides arakawae);
Adults, larvae and eggs of the order Flea, such as the flea family Cat flea (Pulex irritans), dog fleas (Ctenocephalides canis);

Lice, for example, lice (Haematopinidae suis), lice (Haematopinidae eurysternus), lice (Damalinia bovis), lice, lice, lice, lice Adults, larvae and eggs such as (Menopon gallinae);
Dermanyssus gallinus (Arachnid), for example, Dermanyssus gallinus (Varroa jacobsoni), Ixodidae Haemaphysalis longicornis, Ixodes ovatus, Boophilus microplus, Takasagokirama testudinarium), etc., Ornithonyssus sylvialum, etc., Dermanyssus gallinae, etc., Arachnid, Demodex phylloides, etc.

Adults, larvae and eggs of the itch mite family Sarcoptes scabiei bovis, itch mite (Knemidocoptes mutans), itch mite family Otodectes cynotis, itch mite (Psoroptes communis), etc.
C. elegans, C. elegans, for example, Bunostomum pheasum, Pig kidney, Metastrongylus elongata, Hairy nematode, Oesophagostomia, etc .:
Roundworms For example, Ascaris suum, Ascaridia galliate, etc.;
Flatworm phylum flukes, such as Schistosoma japonicum, liver tetsu, deer amphistomiasis, Paragonimus westermani, Japanese chicken egg fluke, etc.;
Tapeworms, such as foliate tapeworms, Moniezia expansus, Moniezia benedensis, square tapeworms, stabbed tapeworms, raillietina cesticillus, etc .:
Root flagellates of the Protozoa phylum Flagellate, eg, Histomonas, etc., Protozoa, eg, Leishmania, Trypanosoma, etc., Multi-flagellate, eg, Giardia, etc.
Amoeba eyes of the fleshy class, such as Entamoeba;
Piroplasma subclasses of the parasitic protozoa, such as Theilaria, Babesia, etc., Late parasitic subclasses, such as Eimeria, Plasmadium, Toxoplasma, etc.

The compound of the present invention can also be used to exterminate harmful organisms that cause direct harm or discomfort to the human body, or to maintain public health conditions for harmful organisms that carry or mediate pathogens. Specific pests include the following.

Lepidoptera of the phylum Arthropod, for example, Yellow-tail (Sphrageidus similis) of the family Dokuga, Kunugia undans of the family Kaleha, Parasa consocia of the family Iraga, Artona martini (Artona martini) Adults, larvae and eggs;
Adults and larvae of the order Coleoptera, such as the longhorn beetle Xanthochroa waterhousei, the blister beetle Epicauta gorhani, and the Staphylinidae Paederus fuscipes.
Adults, larvae and eggs of the order Hymenoptera, such as Vespa simillima xanthoptera of the Vespidaceae family, Brachyponera chinensis of the Ant family, and Batozonellus annulatus of the Spider wasp family;
Flies, for example, Blowfly (Armigeres subalbatus), Ceratopogonidae (Culicoides nipponensis), Chironomus yoshimatsui, etc., Chironomus yoshimatsui, Simulium nikkoense, etc. Ceratopogonidae (Hirosia humilis), Ceratopogonidae (Musca domestica), Ceratopogonidae (Fannia canicularis), Blowfly (Phormia regina), Ceratopogonidae (Sarcophaga peregna) Adults, larvae and eggs;

Adults, larvae and eggs of the order Flea, such as the human flea (Pulex irritans) of the family Flea family;
Adults, larvae and eggs of the order Cockroach, such as the American cockroach (Blattella germanica), the American cockroach (Periplaneta americana), the Smokybrown cockroach (Periplaneta fuliginosa), and the Japanese cockroach (Periplaneta japonica);
Adults, larvae and eggs of the order Orthoptera, such as Diestrammena japonica and Diestrammena apicalis of the family Cricketidae;
Adults, larvae and eggs of the order Lice, such as head lice (Pediculus humanus humanus) of the family Primate body lice, and lice (Phthirius pubis) of the family lice;
Adults, larvae and eggs of the Reduviidae, Assassin bugs (Isyndus obscurus), such as the order Hemiptera, for example, Bed Bugs (Cimex lectularius);

Adults, larvae and eggs of the phylum Arthropod Collembola, for example, the Collembola (Hypogastrura communis) of the family Collembola;
The order Arachnid of the phylum Arachnid, such as the itch mite (Ixodes persulcatus) of the tick family, the itch mite (Ornithonyssus bacoti) of the mosquito family, the demodex folliculorum (Chelacaropsis moorei), etc. Ventricosus, etc., Demodex folliculorum, Demodex folliculorum, Dermotophagoides pteronyssinus, Sarcoptes scabiei, Arachnid, Trombicula akamushi, etc. ;
Authentic spiders, such as the jumping spider (Chiracanthium japonicum), the jumping spider (Heteropoda venatoria), the spider spider (Spermophora senoculata), the spider (Pholcus ), Etc. Adults, larvae and eggs of the jumping spider family Plexippus paykulli, Plexippus adansoni, etc.;

Adults, larvae and eggs of the order Scorpion, such as Isometrus europaeus of the family Scorpionidae;
Adults, larvae and eggs of the order Scolopendra of the arthropod phylum Scolopendra, such as Scolopendra subspinipes mutilans and Scolopendra subspinipes japonica;
Adults, larvae and eggs of the order Centipede, such as the Centipede (Thereuronema hilgendofi);
The order Polydesmida of the phylum Arthropod, such as adults, larvae and eggs of the family Polydesmida (Oxidus gracilis);
Arthropod Phylum Crustaceans, such as adults, larvae and eggs of the woodlouse (Porcellio scaber) of the woodlouse family;
Annelida phylum Haemadipsa zeylanica japonica, for example, Haemadipsa zeylanica japonica;
Trichophyton rubrum, Trichophyton mentagrophytes, etc., Candida albicans, etc., Aspergillus fumigatus, etc., Escherichia coli, Pseudomonas aeruginosa, etc., Gram-negative bacteria, Staloc Gram-positive bacteria such as aureus.

The compounds of the present invention are of particular value in controlling pests such as arthropods, gastropods, nematodes and fungi that damage agricultural crops, natural forests, plantations and trees and ornamental plants in urban green areas. is there. In such situations, the compounds of the present invention are in their commercially useful formulations and in the forms of use prepared by those formulations, other active compounds such as pesticides, acaricides, nematodes, fungicides. It can also exist as a mixture with agents, synergists, plant growth regulators, poison bait or herbicides.
Examples of usage include wettable powders, granule wettable powders, dry flowable agents, water solvents, emulsions, liquids, oils, flowable agents such as suspensions in water and emulsions in water, capsules, powders, granules, and fine powders. Granules, baits, tablets, sprays, fumes, aerosols, etc. can be taken. In order to obtain these dosage forms, various pesticide supplements conventionally used in the technical field of agricultural and horticultural chemicals can be appropriately used. Such pesticide aids can be used, for example, for the purpose of improving the effect, stabilizing, and improving the dispersibility of agricultural and horticultural chemicals.

Examples of the pesticide auxiliary agent include carriers (diluents), emulsifiers, wettable powders, dispersants, disintegrants and the like. Examples of the liquid carrier include water, aromatic hydrocarbons such as toluene and xylene, alcohols such as methanol, butanol and glycol, ketones such as acetone, amides such as dimethylformamide, sulfoxides such as dimethyl sulfoxide, and methylnaphthalene. , Cyclohexane, animal and vegetable oils, fatty acids and the like. As the solid carrier, clay, kaolin, talc, diatomaceous earth, silica, calcium carbonate, montmorillonite, bentonite, feldspar, quartz, alumina, sawdust, nitrocellulose, starch, arabic rubber and the like can be used.
As the emulsifier and dispersant, ordinary surfactants can be used. For example, anionic surfactants such as higher alcohol sodium sulfate, stearyltrimethylammonium chloride, polyoxyethylene alkylphenyl ether, and lauryl betaine. , Cationic surfactants, nonionic surfactants, amphoteric surfactants and the like can be used.
Further, a wetting agent such as dialkyl sulfosuccinate; a fixing agent such as carboxymethyl cellulose and polyvinyl alcohol; a disintegrant such as sodium lignin sulfonate and sodium lauryl sulfate can be used.
Of course, the compound of the present invention may be blended as an active ingredient by one kind or a combination of two or more kinds. The content of the compound of the present invention as an active ingredient in these preparations is, for example, 0.01 to 99.5% by mass, preferably selected from the range of 0.5 to 90% by mass, and the formulation form, application method, etc. It may be appropriately determined according to various conditions, but for example, it is about 0.5 to 20% by mass, preferably about 1 to 10% by mass for the powder, and about 1 to 90% by mass, preferably 10 for the wettable powder. It can be produced so as to contain an active ingredient of about 1 to 80% by mass, preferably about 1 to 90% by mass, preferably 10 to 40% by mass of the emulsion.

To control arthropods, abdominals, nematodes, and fungi, the foliage of plants is usually located in areas where damage is occurring or may occur due to these pests. In addition to spraying on soil, all layers of soil, arthropod application, floor soil mixture, cell seedling treatment, planting hole treatment, plant root treatment, top dress, rice box treatment, water surface application, etc. It can also be used by absorbing it from. It can also be used by dipping seeds in chemicals, seed powder coating, seed treatment such as calper treatment, application to nutrient solution in hydroponic cultivation, smoking or tree trunk injection. When used, the amount of active ingredient per 10 ares is generally 0.1 to 1000 g, preferably 1 to 100 g, although it varies depending on the type and amount of harmful organisms, the type of target crop / tree, cultivation form, and growing condition. To apply. To treat this, dilute with water for wettable powders, granule wettable powders, dry flowable agents, aqueous solvents, emulsions, liquids, flowable agents such as suspensions in water and emulsions in water, and capsules. Although it depends on the type of target plant, cultivation form and growing condition, it is generally sufficient to spray it on crops at an application rate of 10 to 1000 liters per 10 ares. Further, in the case of powders, sprays or aerosols, the crops or the like may be treated in the state of the preparation.
When the target pests mainly harm plants in the soil, or when the chemicals are absorbed from the roots to control the target pests, for example, the preparation is not diluted or diluted with water. A method of applying to a plant stock or a nursery for raising seedlings, a method of spraying granules on a plant stock or a nursery for raising seedlings, a powder, a wettable powder, and granulated water before sowing or transplanting. Method of spraying Japanese medicine, granules, etc. and mixing with the whole soil, powder, wettable powder, granule wettable powder, granules, fine granules, etc. in planting holes, streaks, etc. before sowing or planting plants Etc. can be mentioned as a method of spraying. Wettable powders, granule wettable powders, aqueous solvents, emulsions, liquids, flowable agents such as suspensions and emulsions in water, capsules, etc. are diluted with water and generally applied at a dose of 5 to 500 liters per 10 ares. Then, it may be sprayed on the soil surface or irrigated into the soil so as to be evenly distributed over the entire area to be treated. In the case of powders, granules, fine granules or baits, etc. It should be sprayed on the soil surface so as to be. Spraying or irrigation may be around seeds or crops / trees that you want to protect from harm. It can also be cultivated during or after spraying to mechanically disperse the active ingredient.

As a method of applying paddy rice to a nursery box, the dosage form may differ depending on the application time such as application at the time of sowing, application during the greening period, application at the time of transplantation, etc., for example, powder, granule wettable powder, granule, fine. It may be applied in a dosage form such as granules. It can also be applied by mixing with hilling soil, and it is possible to mix hilling soil with powder, granule wettable powder, granules or fine granules, for example, hilling soil mixing, soil covering mixing, mixing with the entire hilling soil, etc. it can. Alternatively, the soil and various preparations may be applied in layers alternately.
As a method of application to paddy fields, solid preparations such as jumbo preparations, pack preparations, granules and granule wettable powders, and liquid preparations such as flowables and emulsions are usually sprayed on paddy fields in a flooded state. In addition, at the time of rice planting, an appropriate preparation can be sprayed or injected into the soil as it is or mixed with fertilizer or the like. Further, by using a chemical solution such as an emulsion or a flowable as an inflow source of water into a paddy field such as a water outlet or an irrigation device, it can be applied labor-savingly with the supply of water.
Examples of the seed treatment method include diluting a liquid or solid preparation or immersing the seed in a liquid state without diluting it to allow the drug to adhere and permeate, and mixing the solid preparation or the liquid preparation with the seed. Examples thereof include a method of coating the seeds with a powder coating, a method of mixing with an adhesive carrier such as a resin or a polymer and coating the seeds, and a method of spraying the seeds at the same time as planting. The "seed" for which the seed treatment is performed means a plant body in the early stage of cultivation used for plant reproduction, for example, in addition to seeds, bulbs, tubers, seed potatoes, plant buds, propagules, scales or nutrients for cuttings. Plants for reproduction can be mentioned. The "soil" or "cultivation carrier" of the plant in the case of application indicates a support for cultivating a crop, particularly a support for growing roots, and the material is not particularly limited, but the plant can be used. Any material that can grow may be used, so-called soil, seedling mat, water, etc., and specific materials include, for example, sand, pebble, vermiculite, diatomaceous earth, agar, gel-like substance, and high molecular weight substance. Examples include rock wool, glass wool, wood chips, and bark.
As the sowing of the cultivated plant to be transplanted and the treatment during the seedling raising period, in addition to the direct treatment on the seeds, the seedbed for raising seedlings is preferably irrigated with a liquid chemical or sprayed with granules. It is also preferable to treat the granules in the planting holes at the time of planting or to mix them with a cultivation carrier near the transplanting site.

The compounds of the present invention are also valuable in protecting wood (standing trees, fallen trees, processed wood, stored wood or structural wood) from damage by insects such as termites or corns and fungi. In such situations, it is possible to control wood or the soil around it by spraying / injecting / irrigating / applying oils, emulsions, wettable powders, sols, and spraying powders, granules, etc. it can. In addition, the oil, emulsion, wettable powder, powder, etc. used in this scene are mixed with other active compounds such as insecticides, acaricides, nematodes, bactericides, repellents, or synergists. It can also be present as an agent, with the total amount of active ingredient compounds in these formulations 0.0001-95% by weight, preferably 0.005-10% by weight for oils, powders and granules, emulsions, wettable powders and sols. Can contain 0.01 to 50% by mass. When controlling arthropods or fungi, spray 0.01 to 100 g of the active ingredient compound per 1 m ² on the soil or wood surface.

The compounds of the present invention can be used for lepidoptera, corns, mites and other products when stored as-is, powdered or mixed in products such as cereals, fruits, nuts, spices and tobacco. It can be used to protect against damage from fungi. Also, when storing animal products (skin, hair, wool, feathers, etc.) and plant products (cotton, paper, etc.) in a natural or converted state, from the attack of Lepidoptera, Kochu, stains and cockroaches It can be protected and can be protected from attacks by lepidoptera, cockroaches, flies and mites when storing foods such as meat and fish. In such situations, methods such as spraying oils, emulsions, wettable powders, powders, etc., installing resin transpiration agents, treating smoke agents and fumes, installing granules, tablets and poison bait, spraying aerosol, etc. Can be controlled with. These formulations may also be present as a mixture with other active compounds such as pesticides, acaricides, nematodes, fungicides, repellents or synergists, and are included in these formulations. Can contain 0.0001-95% by weight of the active ingredient compound in total.

The compounds of the present invention spread or spread diseases of arthropods and fungi, humans and domestic animals that parasitize the body surface of humans and domestic animals and cause direct harm such as skin feeding or blood sucking. It is valuable for the control or prevention of arthropods, nematodes, trematodes, tapeworms, protozoa, and arthropods that cause discomfort to humans. In such situations, a small amount of the compound of the present invention may be mixed into a meal or feed, or an appropriate orally ingestible compounded drug composition or the like, for example, tablets, pills, containing a pharmaceutically acceptable carrier or coating substance, etc. Oral administration as capsules, pastes, gels, beverages, medicated feeds, medicated drinking waters, medicated supplements, releaseable large pills, and other releaseable devices held in the gastrointestinal tract, or sprays, powders, It can be transdermally administered as a grease, cream, ointment, emulsion, lotion, spot-on, pore-on, shampoo or the like. In order to achieve the effect in such an application, the active ingredient compound is generally contained in the preparation in an amount of 0.0001 to 0.1% by mass, preferably 0.001 to 0.01% by mass. As a method of transdermal administration or local administration, a device (for example, a collar, a medallion, an ear tag, etc.) attached to an animal so as to control arthropods locally or systemically can also be used.

Specific oral administration methods and transdermal administration methods when the compound of the present invention is used as an anthelmintic agent for animals such as livestock and pets or humans are shown, but the present invention is not necessarily limited thereto.
When administered orally as medicated drinking water, the beverage is usually dissolved, suspended or dispersed in a suitable non-toxic solvent or water with a suspending agent such as bentonite or a wetting agent or other excipient. is there. Beverages generally also contain an antifoaming agent. Beverage formulations generally contain 0.01-1.0% by weight, preferably 0.01-0.1% by weight, of the active ingredient compound.
When it is desirable to administer orally in a unit-use form of a dry individual, capsules, pills or tablets containing a predetermined amount of the active ingredient are usually used. These uses are made by homogeneously mixing the active ingredient with appropriately finely ground diluents, fillers, disintegrants and / or binders such as starch, lactose, talc, magnesium stearate, vegetable rubber and the like. Manufactured. Such unit-use formulations can vary widely in mass and content of anthelmintic depending on the type of host animal being treated, the degree of infection and the type of parasite and the weight of the host.

When administered by animal feed, it can be uniformly dispersed in the feed, used as a top dressing or in the form of pellets. Usually, in order to achieve the desired antiparasitic effect, the final feed contains 0.0001-0.05% by weight, preferably 0.0005-0.01% by weight of the active ingredient compound.
Dissolved or dispersed in a liquid carrier excipient can be administered parenterally to animals by intragastric, intramuscular, intratracheal or subcutaneous injection. For parenteral administration, the active compound is preferably mixed with a suitable vegetable oil such as peanut oil, cottonseed oil. Such formulations generally contain 0.05-50% by weight, preferably 0.1-5.0% by weight, of the active ingredient compound.
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 outer surface of the animal by spraying or direct injection.
In addition, the compound of the present invention is used as an insecticide for arthropods that cause direct harm or arthropods that are vectors of diseases, and is an oil agent for the surrounding environment in which those harmful organisms may be latent. , Emulsion, wettable powder, etc. spraying / injection / irrigation / coating, powdering agent, fumigant, mosquito repellent incense, self-burning smoke agent, chemical reaction type smoke agent, etc. Treatment of fumigants, ULVs, etc., installation of granules, tablets and poison bait, or addition of floating powders, granules, etc. to water channels, wells, reservoirs, reservoirs and other running or stagnant water. It can also be used. Furthermore, it is possible to control mosquitoes, which are also agricultural and forest pests, in the same manner as described above, or to mix flies, etc. in livestock feed and mix them with feces. For mosquitoes and the like, a method of volatilizing them into the air with an electric mosquito catcher or the like is also effective. The preparations in these usage forms can also exist as a mixture with other active compounds such as pest control agents, mite control agents, nematode control agents, disease control agents, repellents or synergistic agents. , The active ingredient compound is contained in these preparations in a total amount of 0.0001 to 95% by mass.

The compound of the present invention can also exist as a mixture with other active compounds. Especially for controlling pests such as arthropods, abdominals, and nematodes that damage plants by mixing with compounds (insecticides) that have pest control activity, mite control activity, or nematode control activity. On the other hand, the number of pests to be controlled can be expanded, and synergistic effects such as reduction of drug dose can be expected. Specific examples of the active compound include the following.

Organic phosphorus agents such as acephate, azinphos-methyl, chlorpyrifos, daizinon, dichlorvos, dimeton-S-methyl, dimethoate, Dimethylvinphos, disulfoton, ethion, fenitrothion, fenthion, isoxathion, malathion, metamidophos, methidathion, monochromotophos. monocrotophos, naled, oxideprofos, parathion, phenthoate, phosalone, pyrimiphos-methyl, pyridafenthion, profenofos, prothios ), Propaphos, pyraclofos, salithion, sulprofos, thiometon, tetrachlorvinfos, trichlorphon, vamidothion, etc .;
Carbamate agents such as alanycarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, fratiocarb. (Furathiocarb), isoprocarb, metomyl, metolcarb, pyrimicarb, propoxur, thiodicarb, etc .;
Organochlorines such as aldrin, chlordane, DDT (p, p'-DDT), endosulfan, lindane, etc .;

Pyrethroids such as acrinathrin, allethrin, bifenthrin, cycloprothrin, cyhalothrin, cyhalothrin, cyphenothrin, cypermethrin, delta deltamethrin, ethofenprox, fenpropathrin, fenvalerate, flucythrinate, flufenprox, fluvalinate, furamethrin, halophen Prox (halfenprox), imiprothrin (imiprothrin) permethrin (permethrin), phenothrin (phenothrin), prallethrin (prallethrin), pyrethrin (pyrethrins), resmethrin (resmethrin), silafluofen (silafluofen), tefluthrin (tefluthrin), tefluthrin (tefluthrin) Transfluthrin, etc .;

Neonicotinoid agents such as acetamiprid, clothianidin, dinotefran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, etc .;
Diamide agents such as chlorantraniliprole, cyantraniliprole, cycloaniliprole, flubenziamid, tetraniliprole, etc .;
Phenylpyrazole agents such as ethiprole, fipronil, acetoprole, pyrafluoprole, pyriplore, etc .;

Neristoxin agents, such as bensultap, cartap, thiocyclam, thiosultap, etc .;
Insect growth regulators such as phenylbenzoylurea and diacylhydrazines, such as chlorfluazuron, diflubenzuron, flufenoxuron, hexaflumuron, lufenuron, novallon. (Novaluron), teflubenzuron (teflubenzuron), triflumuron, buprofezin, chromafenozide, halofenozide, methoxyfenozide, tebufenozide, cyromazine, etc.
Juvenile hormones such as diofenolan, fenoxycarb, hydroprene, metoprene, pyriproxyfen, etc .;

Insecticides produced by microorganisms, such as abamectin, emamectin-benzoate, ivermectin, lepimectin, milbemectin, nemadectin, Nikkomycin. , Polyoxin complex (polioxin), spinetram (spinetram), spinosad (spinosad), BT agent, etc.;
Insecticide derived from natural substances, such as anabasine, azadiractin, deguelin, fatty acid glyceride (decanolyoctanoylglycerol), hydroxy propyl ester, soybean lecithin, nicotine. ), Nornicotine, oreic acid sodium salt, machine oil (petroleum oil), propylene glycol monolaurate, rape oil, rotenone, sorbitan fatty acid ester ( Sorbitan fatty acid ester), starch (starch), etc .;

Other pesticides include, for example, afidpyropen, benzpyrimoxan, broflanilide, chlorfenapyr, diafenthiuron, dicloromezotiaz, dimpropyridaz. ), DBEDC (Dodecylbenzenesulphonic acidbisethylenediamine copper [II] salt), Flonicamid, flometoquin, flufenerim, flupyradifurone, flupyrimin, flupyrimin, fluralanel, fluralaner fluxametamide), hydramethylnon, indoxacarb, isocycloseram, metaflumizone, metaldehyde, nicotine sulfate, oxazosulfyl, Pymetrozine, pyridalyl, pyrifluquinqzon, spirotetramat, sulfoxaflor, tolfenpyrad, triazamate, triflumezopyrim, triflumezopyrim )etc;

Acaricides such as acequinocyl, acynonapyr, amidoflumet, amitraz, azocyclotin, benzoximate, bifenazate, binapacryl, phenisobromo. Rate (bromopropylate), quinomethionat, clofentezine, cyenopyrafen, cyflumetofen, tricyclohexatin hydroxide (cyhexatin), dicofol (dicofol), dienochlor, ethoxazole , Fenazaflor, fenazaquin, fenbutatin oxide, fenothiocarb, fenpyroximate, fluacrypyrim, hexythiazox, hexythiazox, pyrimidifen, pirimidifen Propargite, pyflubumide, pyridaben, spirodiclofen, spiropidion, spiromesifen, tebufenpyrad, tetradifon and KUI-1821 (test name) )etc:

Nematode killing agents such as aluminum phosphide, benclothiaz, cadusafos, ethoprophos, fluazaindolizine, fluensulfone, fosthiazate, fusthiazate. furfural, imicyafos, levamisol hydrochloride, mesulfenfos, metam-ammonium, methyl isothiocyanate, moranteltartarate, oxamyl, thioxazafen, etc. ;
Poisonous baits such as chlorphacinone, coumatetralyl, diphacinone, sodium fluoracetate, warfarin and the like can be mentioned.

The compound of the present invention can also exist as a mixture with an active compound other than a compound having pest control activity, mite control activity or nematode control activity. In order to control diseases and / or weeds that occur at the same time as the time of use, by using it in combination with a compound having bactericidal activity, herbicidal activity or plant growth regulator activity, it is possible to reduce the control labor and the amount of drug. Synergistic effects can also be expected. Further, by using it in combination with a repellent or a synergistic agent, a more effective control effect such as a synergistic effect can be expected.

As a specific example of the active compound, a disease control agent, for example,
DD (1,3-dichloropropene), acibenzolar-S-methyl, aldimorph, ametoctradin, amisulbrom, andoprim, anilazine, azaconazole , Azoxystrobin, basic copper sulfate, benodanil, benomyl, benthiavalicarb-isopropyl, benthiazole, bitertanol , Bixafen, blasticidin S, boscalid, bromuconazole, calcium carbonate, buthiobate, lime sulfur, captan captafol, captan, carbendazim, carboxin, carpropamid, chinomethionat, chlorfenazole, chlorofenazole, chloropicrin, chlorothalonil , Chlozolinate, DBEDC (complex of bis (ethylenediamine) copper-bis- (dodecylbenzenesulfonic acid)), cupper hydroxide,

Copper nonylphenol sulfonate, copper oxygen chloride, cyazofamid, cyflufenamid, cymoxanil, cyproconazole, cyprodinil, dazomet , Diclobutrazol, dichlofluanid, dichlone, dichlocymet, dichromezine, diethofencarb, diphenoconazole, dimethomorphometo, diflumetorim , Dimoxystrobin, diniconazole (diniconazole), diniconazole M (diniconazole-M), dithane-stainless, dithianon, dodine, echlomezole, edifenphos ), Enestrobin, epoxiconazole, etaconazole, ethaboxam, extract from mushroom, famoxadone, fenamidone, fenamidone, fenamidone, fenamidone, fenamidone Fenbuconazole, fenfuram, fenhexamid, fenoxanol, fenpiclonil, fenpropidin, fenpyrazamine, ferimzone, fluazinam ), Flumetover, flumorph, fluopicolide, fluopyram, flu Fluorimide, fluotrimazole, fluoxastrobin,

Fluquinconazole, flusulfamide, flutolanil, fluxapyroxad, folpet, fosetyl-AL, fthalide, fuberidazole, fludioxonyl (Fludioxonil), flusilazole, flutianil, flutriafol, furametpyr, furametpyr, furconazole, guazatine, hexaconazole, hydroxyioxazole , Hymexazol, imazalil, imazalil sulfate, imibenconazole, iminoctadine acetate, iminoctadine Albesilate (iminoctadine-DBS), imponoctadine-DBS (Iprobenfos), iprodione, iprovalicarb, isofetamid, isoprothiolane, isopyrazam, isotianil, kasugamycin, cresoxim-methyl mancozeb), mandipropamid, maneb,

Manzeb, mepanipyrim, mepronil, metalaxyl, carbam (metam-ammonium), carbam sodium (metam-sodium), metconazole (metconazole), metasulfocarb (methasulfocarb), bromide Methyl (methyl bromide), methyl isothiocyanate (methylisothiocyanate), metminostrobin (metominostrobin), metrafenone (metrafenone), mildiomycin (mildiomycin), microbutanil (myclobutanil), organic sulfur nickel salt (nickel dimethyldithiocarbamate), nuarimol (nuarimol) , Orysastrobin, oxadixyl, oxathiapiprolin, organic copper (oxine-copper), oxolinic acid, oxpoconazole fumarate, oxycarboxyne (oxpoconazole fumarate) oxycarboxin, oxytetracycline, pebulate, pefurazoate, penconazole, peniccuron, penflufen, penthiopyrad, picarbutrazox, picarbutrazox, picocarboxin, oxytetracycline, pebulate, pefurazoate, penconazole, pencicuron, penflufen, penthiopyrad, picarbutrazox Robin (picoxystrobin), piperalin (piperalin), polycarbamate (polycarbamate), polyoxin-B (polyoxin-B), polyoxin complex (polyoxins), potassium hydrogen carbonate (potassium hydrogen carbonate),

Probenazole, prochloraz, procymidone, propamocarb, propiconazole, propineb, proquinazid, prothioconazole, pyraclostrobin , Pyrametostrobin, pyraoxystrobin, pyrazophos, pyribencarb, pyridinitril, pyrifenox, pyrimetanil, pyriophenone, pyriofenone , Kinoxyfen, quintozene, sedaxane, silver (silver), simeconazole, sodium hydrogen carbonate (sodium hydrogen carbonate), sodium hypochlorite (sodium hypochlorite), spiroxamine (spiroxamine), Streptomycin, sulfur, tebfloquin, tebuconazole, tecloftalam, terbinafine, tetraconazole, thiabendazole, thiadiazin, thiadiazin, thiadiazin ), Thiophanate,

Thiophanate-methyl, thiram, tiadinil, tolclofos-methyl, tolprocarb, tolylfluanid, triadimefon, triadimenol, triadimenol, triadimenol, triadimefon, triadimefon, triadimefon, triadimefon Piricalve (triclopyricarb), tricyclazole, tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole, uniconazole-P ), Validamycin (-A), vinclozolin, zarilamid, zinc sulfate, zineb, ziram, zoxamide and the like can be exemplified.

As a compound having herbicidal activity, for example,
Aclonifen, acifluofen-sodium, alachlor, alloxydim, amicabazone, amidosulfuron, anilofos, ashlam, atrazine (aclonifen) atrazine), azimsulfuron, benfuresate, bensulfuron-methyl, bentazone, benthiocarb, benzobicyclon, benzofenap, bialaphos ), Bifenox, Bromoxynil, Bromoxynil, butamifos, cafenstrole, calcium peroxide, carbetamide, cinosulfuron, clomeprop, clomeprop Cyclosulfamuron, cyhalofop-butyl, daimuron, desmedipham, diclohop-methyl, diflufenican,

Dimefuron, dimethametryn, dinoterb, diquat, diuron, esprocarb, ethiozin, ethofumesate, ethoxysulfuron, ethoxysulfuron, ethofumesate, ethoxysulfuron ), Fenoxaprop-P-ethyl, fentrazamide, flucarbazone, flufenacet, flurtamone, fluthiacet-methyl, horamsulfuron (fluthiacet-methyl) foramsulfuron, glufosinate-ammonium, glyphosate-isopropylamine salt, glyphosate-trimesium, imazapyr, imazosulfuron, indanofan iodosufluron), ioxynil-octanoate, isoproturon, isoxadifen, isoxaflutole, lactofen, linuron,

Mefenacet, mesosulfuron, metamitron, metabenzthiazuron, metosulam, metribuzin, napropamide, neburon, oxadiargyl (Oxadiazon), oxaziclomefone, paraquat, pendimethalin, pentoxazone, phenmedipham, pretilachlor, propoxycarbazone, prosulfocarbazone, prosulfocarbazone (oxadiazon), oxaziclomefone (oxaziclomefone), paraquat (paraquat), pendimethalin (pendimethalin), pentoxazone (pentoxazone), phenmedipham (phenmedipham), pretilachlor (pretilachlor), propoxycarbazone. ), Pyraclonil, pyraflufe n-ethyl, pyrazolate, pyrazosulfuro n-ethyl, pyribticarb, pyriftalid, pyriminobac-methyl , Quizalofop-ethyl, setoxydim (sethoxydim), simazine, sulcotrion, sulfentrazone, thenylchlor, triaziflam, tribufos, etc. Can be exemplified.

Further, as a compound having a plant growth regulating action, for example,
1-naphthylacetamide (1-naphthylacetic acid), 4-CPA (4-CPA), benzylaminopurine (6-benzylaminopurine), butralin, calcium chloride, calcium formate, peroxidation Calcium peroxide, calcium sulfate, chlormequat chloride, choline, cyanamide, cyclanilide, daminozide, decyl alcohol, dichlorprop ( dichjoprop, ethephon, ethychlozate, flurprimidol, forclorfenuron, gibberellic acid, indolebutyric acid, hydrazide potassium maleate salt, mefenpyr, mepiquat chloride, oxine sulfate, 8-hydroxyquinoline sulfate, paclobutrazol, paraffin, prohexadione calcium salt. -calcium),

It can also be used in combination with prohydrojasmon, thidiazuron, trinexapac, uniconazole-P, wax, and the like.
Repellents For example, capsaicin, carane-3,4-diol, citronellal, deet, dimethyl phthalate, hinokitiol, limonene. , Linalool, menthol, menthone, naphthalene, thiram, etc .;
Colytic agents such as methylenedioxynaphthalene, naphthyl propynyl ether, nitrobenzyl thiocyanate, octachlorodipropyl ether, pentynyl phthalimide, phenyl salioxon, piperonil butoxide, safrole, sesamex, sesamin, sulfoxide, triphenyl phosphate, verbutin Etc. can be mentioned.

The compounds of the present invention can be used as biopesticides, for example, cytoplasmic polyhedrosis virus (CPV), insect poxvirus (EPV), granulosis virus (GV), nuclear polyhedrosis virus (GV), nuclear polyhedrosis virus (CPV), and nuclear polyhedrosis virus (CPV). Viral preparations such as Nuclear polyhedrosis virus (NPV), Beauveria bassiana, Beauveria brongniartii, Monocrosporium phymatophagum, Pekilomyces phymatophagum, Pekilomyces fumosolopes transpemoriaces ), Steinernema carpocapsae, Steinernema glaseri, Steinernema kushidai, Verticillium lecanii, etc. Micropesticide, Agrobacterium radiobactor, Bacillus subtilis, non-pathogenic Erwinia carotovora, non-pathogenic Fusarium oxysporum, Pseudomonas CAB-02 Pseudomonas CAB-02), Pseudomonas fluorescens, Talaromyces flavus, Trichoderma atroviride, Trichoderma atroviride, Trichoderma lignolan pesticides used as pesticides -Similar effects can be expected by mixing with biopesticides used as herbicides such as Campestris (Xanthomonas campestris).

Further, as biological pesticides, for example, Amblyseius californicus, Amblyseius cucumeris, Amblyseius degenerans, Aphidius colemani, Aphidius colemani, Aphidius colemani, Aphidius colemani, Aphidius colemani, Aphidius colemani (Chrysoperia carnea), Hamoglycomayu bee (Dacnusa sibirica), Isaea Himekobachi (Diglyphus isaea), Onshitsutsuyakobachi (Encarsia formosa), Sabakutsuyakobachi (Eretmocerus eremicus), Arigatashima thrips (Franklyseius) , Kanmurihimekobachi (Hemiptarsenus varicornis), Hamogurimidorihimekobachi (Neochrysocharis formosa), Namihimehanakamemushi (Orius sauteri), Tairikhimehanakamemushi (Orius strigicollis), Chili mosquito (Phytoseiulus persimilis) Natural enemy creatures such as Piocoris varius, codlelure, cuelure, geraniol, gyptol, liblure, looplure, methyl eugenol, orfralure , Peachflure, phycilure, pyrimalure, turpentine, and other pheromone agents can also be used in combination.
Example

Hereinafter, the present invention will be described in detail by describing Examples, Formulation Examples and Test Examples, but the scope of the present invention is not limited to these Examples, Formulation Examples and Test Examples.

Example 1.2 Synthesis of 1,4-dimethyl-1- (1,1,1-trifluoroethyl) thiobenzene A solution of 2,4-dimethylbenzenethiol (14.7 mL) in DMF (200 mL) is cooled in an ice bath. Then, potassium carbonate (18.3 g) and benzene (5.17 g) were added. On the other hand, 2,2,2-trifluoroethyl iodide (25.1 g) was added dropwise over 25 minutes, and the mixture was stirred in an ice bath for 3 hours and the reaction solution was heated to room temperature for 22 hours. The reaction was poured into ice water and extracted 3 times with hexane. The combined organic layers were washed with saturated brine and dried over sodium sulfate. The solvent was distilled off under reduced pressure to obtain 23.2 g of 2,4-dimethyl-1- (1,1,1-trifluoroethyl) thiobenzene.

Example 2.2 Synthesis of 2,4-dimethyl-5-[(1,1,1-trifluoroethyl) thio] benzaldehyde 2,4-dimethyl-1- (1,1) in a 3-diameter flask equipped with a dropping funnel. , 1-Trifluoroethyl) Thiobenzene (10.0 g) was added, and the inside of the container was replaced with argon. To this, 100 mL of dry dichloromethane was added, and the mixture was cooled in an ice bath. In response, 100 mL of titanium tetrachloride (1.0 M dichloromethane solution) was added dropwise over 3 hours. After stirring in an ice bath for 13 minutes, dichloromethyl methyl ether (4.46 mL) was slowly added, and the mixture was stirred for 2.5 hours while raising the temperature to room temperature, and further stirred at room temperature for 16 hours. Then, the reaction solution was poured into a saturated aqueous solution of ammonium chloride to separate the organic layer. The aqueous layer was extracted twice with hexane, and the combined organic layer was washed twice with 0.1 N hydrochloric acid and once with saturated brine. This was dried over sodium sulfate, and then the organic solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane: EtOAc = 10: 1 / Rf = 0.2) to add 7.82 g of 2,4-dimethyl-5-[(1,1,1-trifluoroethyl) thio] benzaldehyde. Obtained.

Example 3.2 Synthesis of 2,4-dimethyl-5-[(1,1,1-trifluoroethyl) sulfinyl] benzaldehyde 2,4-dimethyl-5-[(1,1,1-trifluoroethyl) thio ] Benzaldehyde (1.07 g) was dissolved in 8 mL of methanol, 35% hydrogen peroxide solution (0.420 mL) and sodium tungstate dihydrate were added, and the mixture was stirred at room temperature for 16 hours. Then water is added, the precipitated solid is filtered off, washed with water and dried to give 0.860 g of a white solid of 2,4-dimethyl-5-[(1,1,1-trifluoroethyl) sulfinyl] benzaldehyde. Obtained.

Example 4.1- (2,4-Dimethyl-5-((2,2,2-trifluoroethyl) sulfinyl) benzyl) -4- (Trifluoromethyl) Piperidine Synthesis 2,4-dimethyl-5- [(1,1,1-Trifluoroethyl) sulfinyl] Dissolve benzaldehyde (341 mg) in 15 mL of dichloromethane, add 4-trifluoromethylpiperidine (0.201 mL) and acetic acid (0.022 mL), and stir for 17 minutes. did. To this, sodium triacetoxyborohydride (389 mg) was added, and the mixture was stirred at room temperature for 3 hours. Ethyl acetate, water and saturated aqueous sodium hydrogen carbonate solution were added to terminate the reaction. The organic layer was separated and the aqueous layer was extracted twice with ethyl acetate. The combined organic layer was dried over saturated brine and sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue is sprinkled on silica gel, purified by silica gel column chromatography (n-hexane: EtOAc = 2: 1 / Rf = 0.5), and 1- (2,4-dimethyl-5-((2,2,2-)). Trifluoroethyl) silica gel) benzyl) -4- (trifluoromethyl) piperidine 416 mg was obtained.

Example 5. Synthesis of (2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl) thio) phenyl) methanol (2-fluoro-4-methyl-5-((2,2,2-tri) Sodium tetrahydroborate (174 mg) was added to a 13 mL solution of fluoroethyl) thio) benzaldehyde (957 mg) in ethanol at room temperature, and the mixture was stirred for 30 minutes. Then, ethyl acetate, water, and 1N hydrochloric acid were added in that order, and ethyl acetate was added. The combined organic layers were washed with saturated brine and dried over sodium sulfate. The residue obtained by distilling off the solvent under reduced pressure was subjected to silica gel column chromatography (n-hexane: EtOAc = 4: 1). Purification with / Rf = 0.5) gave 895 mg of (2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl) thio) phenyl) methanol.

Example 6.2 Synthesis of 2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl) thio) benzylmethanesulfonate (2-fluoro-4-methyl-5-((2,2,2)) 2-Trifluoroethyl) thio) phenyl) methanol (2.85 g) was dissolved in 40 mL of dichloromethane and cooled in an ice bath. To this, methanesulfonyl chloride (2.60 mL) was added, and a 7 mL solution of triethylamine (1.90 mL) in dichloromethane was added dropwise over 25 minutes. This was stirred for 80 minutes while raising the temperature to room temperature, and then water was added. The organic layer was separated and the aqueous layer was extracted once with ethyl acetate. The combined organic layers were washed with saturated brine, dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane: EtOAc = 4: 1 / Rf = 0.3) and 2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl) thio). ) 3.20 g of a colorless oil of benzylmethane sulfonate was obtained.

Example 7.2 Synthesis of 2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl) sulfinyl) benzylmethanesulfonate 2-fluoro-4-methyl-5-((2,2,2) -Trifluoroethyl) thio) benzyl methanesulfonate (208 mg) was dissolved in 8 mL of chloroform, and m-chloroperbenzoic acid (174 mg) was added. After stirring for 35 minutes, a saturated aqueous sodium hydrogen carbonate solution was added and the mixture was stirred. After separating the organic layer, the aqueous layer was extracted twice with chloroform. The combined organic layers were washed with saturated brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (n-hexane: EtOAc = 1: 1 / Rf = 0.5) and 2-fluoro-4-methyl-5-((2,2)). 180 mg of a white solid of 2-trifluoroethyl) silica gel) benzyl methanesulfonate was obtained.

Example 8.1-Synthesis of 2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl) sulfinyl) benzyl) -4-methylpiperidine 2-fluoro-4-methyl-5- ((2,2,2-Trifluoroethyl) sulfinyl) Benzylmethane sulfonate (147 mg) is dissolved in 5 mL of DMF, 4-methylpiperidin (0.052 mL) and potassium carbonate (71.4 mg) are added, and 5 mL of DMF is added. Was added and stirred for 30 minutes. Water was added to stop the reaction, and the mixture was extracted twice with a hexane: ethyl acetate = 4: 1 solvent. The combined organic layers were washed with saturated brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (n-hexane: EtOAc = 1: 1 / Rf = 0.5) and 1- (2-fluoro-4-methyl-5-(((2-fluoro-4-methyl-5-) 2,2,2-Trifluoroethyl) sulfinyl) benzyl) -4-methylpiperidin 112 mg was obtained.

The ¹ H-NMR data of the compounds produced in the same manner as in the above Examples are shown in Table 7 below.
Table 7

The preparations containing the compound of the present invention will be specifically described below with reference to some preparation examples, but the compounds of the present invention, auxiliary components, their addition amounts, etc. are, of course, limited to the following preparation examples. is not. In addition, in the preparation example, all parts are represented by mass parts.

Formulation Example 1 Emulsion Compound of the present invention (10 parts), N-methyl-2-pyrrolidone (reagent) (10 parts), xylene (reagent) (70 parts), New Calgen D-230 (polyoxyethylene castor oil, Takemoto oil and fat) Co., Ltd.) (10 parts) was uniformly mixed and dissolved to obtain an emulsion.

Formulation Example 2 EW-1
The compound of the present invention (20 parts) and New Calgen D-230 (polyoxyethylene castor oil, Takemoto Oil & Fat Co., Ltd.) (15 parts) were mixed and homogenized, and then water (59.8 parts) was stirred. Was gradually added to obtain a dispersion. KELZAN (xanthan gum, Sansho Co., Ltd.) (0.2 parts) in which this dispersion was dispersed in propylene glycol (reagent) (5.0 parts) was added to obtain an emulsion preparation.

Formulation Example 3 EW-2
The compound of the present invention (10 parts) was dissolved in xylene (10 parts) and mixed with Leodor 430V (polyoxyethylene sorbitol tetraoleate, Kao Corporation) (24 parts) to obtain a dispersion. KELZAN (xanthan gum, Sansho Co., Ltd.) (0.2 parts) in which this dispersion and water (50.8 parts) were dispersed using a homogenizer and dispersed in propylene glycol (reagent) (5.0 parts). Was added to obtain an emulsion preparation.

Formulation Example 4 Microemulsion The compound of the present invention (10 parts), xylene (reagent) (20 parts), Neucalgen D-230 (polyoxyethylene castor oil, Takemoto Oil & Fat Co., Ltd.) (20 parts), Airroll CT-1L (Dioctyl) Sodium sulfosuccinate, Toho Chemical Industry Co., Ltd. (2.0 parts) and water (48 parts) were uniformly mixed to obtain a microemulsion.

Formulation Example 5 Water Solvent The compound of the present invention (5 parts), Lunox P-65L (sodium alkylbenzene sulfonate, Toho Chemical Industry Co., Ltd.) (3 parts) and sodium hydrogen carbonate (reagent) (82 parts) were uniformly mixed. Later, it was pulverized using a fine pulverizer to obtain an aqueous solvent.

Preparation Example 6 Liquid -1
The compound of the present invention (20 parts), N-methyl-2-pyrrolidone (reagent) (70 parts) and Neucalgen D-230 (polyoxyethylene castor oil, Takemoto Oil & Fat Co., Ltd.) (10 parts) are uniformly mixed and dissolved. The solution was obtained.

Formulation Example 7 Liquid-2
The compound of the present invention (0.5 part), N-methyl-2-pyrrolidone (reagent) (30 parts), Neucalgen D-230 (polyoxyethylene castor oil, Takemoto Oil & Fat Co., Ltd.) (10 parts) and water (59 parts). .5 parts) was uniformly mixed and dissolved to obtain a liquid preparation.

Formulation Example 8 Wettable Compound (20 parts), Toxil GU-N (White Carbon, Oriental Silicon Corporation) (20 parts), Solpol 5096 (Polyoxyethylene styrylphenyl ether sulfate, Toho Chemical Industry Co., Ltd.) ( 10 parts) and SS clay (clay, Showa KDE Co., Ltd.) (50 parts) were mixed and then pulverized using a fine pulverizer to obtain a wettable powder.

Formulation Example 9 Granule wettable powder The compound of the present invention (50 parts), Sun Extract P252 (sodium lignin sulfonate, Nippon Paper Industries, Ltd.) (5 parts), and SS clay (clay, Showa KDE Co., Ltd.) (45 parts). Was mixed and then pulverized using a fine pulverizer to obtain a pulverized product. Water was added to the pulverized product and kneaded well, then extruded and granulated, and dried and sized to obtain a granule wettable powder.

Formulation Example 10 Slurry agent The compound of the present invention (20 parts), Solpol 7948 (polyoxyalkylene tristyrylphenyl ether sodium sulfate, Toho Chemical Industry Co., Ltd.) (5 parts), propylene glycol (reagent) (10 parts), and water. (40 parts) was mixed in advance and wet-pulverized with a bead mill to obtain a slurry. Next, KELZAN (xanthan gum, Sansho Co., Ltd.) (0.2 parts) was well mixed and dispersed in water (24.8 parts) to prepare a gel-like product, which was thoroughly mixed with the crushed slurry to prepare a flowable agent. Obtained.

Formulation Example 11 Granules-1
The compound of the present invention (5 parts), Airroll CT-1L (sodium dioctyl sulfosuccinate, Toho Chemical Industry Co., Ltd.) (2 parts), bentonite Sado (bentonite, Kunimine Industries Co., Ltd.) (30 parts), and NK-300 (30 parts). Clay, Showa KDE Co., Ltd.) (63 parts) were mixed uniformly, water was added and kneaded well, and then extruded granulation was performed and dried and sized to obtain granules.

Formulation Example 12 Granules-2
The compound (5 parts) of the present invention was dissolved in methanol (reagent), adsorbed on Ishikawa Light No. 2 (95 parts) using a rolling granulator, and dried to obtain granules.

Formulation Example 13 Fine Granules-1
The compound (2 parts) of the present invention was dissolved in methanol (reagent), adsorbed on Ishikawa Light No. 4 (98 parts) using a rolling granulator, and dried to obtain a fine granule.

Formulation Example 14 Fine Granules-2
The compound of the present invention (5 parts) and Toxile GU-N (5 parts) were mixed, pulverized using a fine pulverizer, and uniformly mixed with Iide silica sand (quartz sand, JFE Mineral Co., Ltd.) (80 parts). Toxanone GR-31A (polycarboxylic acid type surfactant, Sanyo Chemical Industries, Ltd.) (10 parts) was further mixed with this mixture while spraying a diluted aqueous solution to obtain a granular composition. The granular composition was dried to obtain a fine granule.

Formulation Example 15 Powdering agent After uniformly mixing the compound of the present invention (5 parts), Toxil GU-N (5 parts) and Omori fine powder clay (clay, Omori Sangyo Co., Ltd.) (90 parts), use a pulverizer. And crushed to obtain a powder.

Next, the action and effect and usefulness of the compound of the present invention will be described with reference to specific examples. The compounds used for comparison and control are indicated by the following compound symbols.

Comparative Agent A (13-24 described in US 2009/0082389 A1)

Test Example 1: A 430 ml capacity polyethylene cup containing test water for killing imago against Tetranychus urticae Koch was covered with a lid having a hole (diameter about 5 mm) in the center. Make a notch with a width of about 5 mm in a circular filter paper with a diameter of 6.5 cm so that a strip-shaped filter paper piece is formed, and immerse the strip-shaped filter paper piece hanging downward from the hole in the lid into the water in the cup. And put cotton wool on the filter paper. In this way, two leaf discs (2 cm x 5 cm) made from the primary leaves of the common bean were placed on absorbent cotton so that the water in the cup was constantly replenished, and 10 adult female spider mites were placed on the leaf discs. Inoculated. This cup was placed in an acrylic cylinder having a height of 50 cm and a diameter of 10 cm, and a water-diluted solution (500 ppm) of an emulsion prepared according to Formulation Example 1 was sprayed at 2.0 ml per cup using an airbrush. After spraying, it was kept in a constant temperature room at 25 ° C. Four days after the treatment, the life and death of the adults and the agony were investigated under the binocular, and the insecticidal rate (%) was determined by killing the agony insects. The test was carried out by using 1 cup in each section.

Insecticidal rate (%) = (number of dead larvae / number of test larvae) x 100

As a result, compound numbers A-1, A-2, A-3, A-4, A-5, A-6, A-7, A-8, A-9, A-10, A-11, A -13, A-14, A-15, A-16, B-1, B-2, B-3, C-1, C-2, C-3, C-4, C-5, C-6 , C-7, D-1, D-2, D-3, D-4 of the present invention showed 100% insecticidal rate. On the other hand, Comparative Agent A had an insecticidal rate of 0%.

Test Example 2: Density suppression test against Tetranychus urticae Koch A 430 ml capacity polyethylene cup containing test water was covered with a lid having a hole (diameter about 5 mm) in the center. Make a notch with a width of about 5 mm in a circular filter paper with a diameter of 6.5 cm so that a strip-shaped filter paper piece is formed, and immerse the strip-shaped filter paper piece hanging downward from the hole in the lid into the water in the cup. And put cotton wool on the filter paper. In this way, two leaf discs (2 cm x 5 cm) made from the primary leaves of the common bean were placed on absorbent cotton so that the water in the cup was constantly replenished, and 10 adult female spider mites were placed on the leaf discs. Inoculated. This cup was placed in an acrylic cylinder having a height of 50 cm and a diameter of 10 cm, and a water-diluted solution (500 ppm) of an emulsion prepared according to Formulation Example 1 was sprayed at 2.0 ml per cup using an airbrush. After spraying, it was kept in a constant temperature room at 25 ° C. Next-generation density suppression effect on eggs laid by adults 7 days after treatment was 100 (density suppression rate: 100%), 95 (same: 99-95%), 80 (same: 94-80%), 50 (same::). Evaluation was made on a scale of 5 (79-50%) and 0 (same: less than 50%), and the next-generation density suppression rate was calculated by the following formula based on the results. The test was carried out by using 1 cup in each section.

Next-generation density suppression rate = (A x 100 + B x 95 + C x 80 + D x 50) / (A + B + C + D + E)

A: 100 discs, B: 95 discs, C: 80 discs, D: 50 discs, E: 0 discs

As a result, compound numbers A-1, A-2, A-3, A-4, A-5, A-6, A-7, A-8, A-9, A-10, A-11, A -13, A-14, A-15, A-16, B-1, B-2, B-3, C-2, C-3, C-4, C-5, C-6, C-7 , D-1, D-2, D-3, D-4 of the present invention showed a density suppression rate of 100%. On the other hand, Comparative Agent A had a density suppression rate of 0%.

Test Example 3: A polyethylene cup having a capacity of 430 ml containing test water for killing imagoes against Panonychus citri McGregor was covered with a lid having a hole (diameter about 5 mm) in the center. Make a notch with a width of about 5 mm in a circular filter paper with a diameter of 6.5 cm so that a strip-shaped filter paper piece is formed, and immerse the strip-shaped filter paper piece hanging downward from the hole in the lid into the water in the cup. And put cotton wool on the filter paper. In this way, two leaf discs (2 cm x 5 cm) made from fully unfolded leaves of citrus fruits were placed on absorbent cotton so that the water in the cup was constantly replenished, and 10 adult female spider mites were placed on the leaf discs. Was inoculated. This cup was placed in an acrylic cylinder having a height of 50 cm and a diameter of 10 cm, and a water-diluted solution (500 ppm) of an emulsion prepared according to Formulation Example 1 was sprayed at 2.0 ml per cup using an airbrush. After spraying, it was kept in a constant temperature room at 25 ° C. Four days after the treatment, the life and death of the adults and the agony were investigated under the binocular, and the insecticidal rate (%) was determined by killing the agony insects. The test was carried out by using 1 cup in each section.

Insecticidal rate (%) = (number of dead larvae / number of test larvae) x 100

As a result, compound numbers A-1, A-2, A-3, A-4, A-5, A-6, A-7, A-8, A-10, A-11, A-13, A -14, A-15, A-16, B-1, B-2, B-3, C-1, C-2, C-3, C-4, C-5, C-6, C-7 , D-1, D-3 of the present invention compound showed 100% insecticidal rate. On the other hand, Comparative Agent A had an insecticidal rate of 0%.

Test Example 4: Density suppression test against Panonychus citri McGregor A 430 ml capacity polyethylene cup containing test water was covered with a lid having a hole (diameter about 5 mm) in the center. Make a notch with a width of about 5 mm in a circular filter paper with a diameter of 6.5 cm so that a strip-shaped filter paper piece is formed, and immerse the strip-shaped filter paper piece hanging downward from the hole in the lid into the water in the cup. And put cotton wool on the filter paper. In this way, two leaf discs (2 cm x 5 cm) made from fully unfolded leaves of citrus fruits were placed on absorbent cotton so that the water in the cup was constantly replenished, and 10 adult female spider mites were placed on the leaf discs. Was inoculated. This cup was placed in an acrylic cylinder having a height of 50 cm and a diameter of 10 cm, and a water-diluted solution (500 ppm) of an emulsion prepared according to Formulation Example 1 was sprayed at 2.0 ml per cup using an airbrush. After spraying, it was kept in a constant temperature room at 25 ° C. Next-generation density suppression effect on eggs laid by adults 7 days after treatment was 100 (density suppression rate: 100%), 95 (same: 99-95%), 80 (same: 94-80%), 50 (same::). Evaluation was made on a scale of 5 (79-50%) and 0 (same: less than 50%), and the next-generation density suppression rate was calculated by the following formula based on the results. The test was carried out by using 1 cup in each section.

Next-generation density suppression rate = (A x 100 + B x 95 + C x 80 + D x 50) / (A + B + C + D + E)

A: 100 discs, B: 95 discs, C: 80 discs, D: 50 discs, E: 0 discs

As a result, compound numbers A-1, A-2, A-3, A-4, A-5, A-6, A-7, A-8, A-9, A-10, A-11, A -13, A-14, A-15, A-16, B-1, B-2, B-3, C-1, C-2, C-3, C-4, C-5, C-6 , C-7, D-1, D-3, D-4 of the present invention showed a density suppression rate of 100%. On the other hand, Comparative Agent A had a density suppression rate of 0%.

Test Example 5: Effect on sweet potato root-knot nematode (Meloidogyne incognita (Kofoid et White) Chitwood) 200 ml of test soil adjusted to 200 nematodes / 20 g of soil was placed in a styrol cup (9 cm in diameter and 6.5 cm in height). , 50 ml of water diluted solution (100 ppm) of the emulsion prepared according to Preparation Example 1 was irrigated, and then tomatoes were sown (13 grains / pot). After sowing, it was grown in a greenhouse. On the 14th day of sowing, the degree of root hump of each strain was investigated in 5 stages based on the following evaluation criteria, and the Nekobu index and the control value were calculated based on the following formula. The test was carried out by using 1 pot in each section.
Degree of root hump (evaluation standard): 0 (no root hump), 1 (1-2 root humps), 2 (3 or more root humps), 3 (large root hump or connected root hump) Yes. Less than 50% of all roots) 4 (More than 50% of all roots have root humps)

Root bump index = Σ (root hump degree x number of relevant shares) / (4 x number of surveyed shares)

Control value (%) = [1- (Root bump index of treated plot / Root bump index of untreated plot)] x 100

As a result, the compounds of the present invention of Compound Nos. A-3, A-7, A-8, A-10, B-1, B-2, B-3 and C-3 showed a control value of 80% or more. .. On the other hand, Comparative Agent A had a control value of 0%.

Test Example 6: A 430 ml capacity polyethylene cup containing test water for killing larvae against Bemisia tabaci (Biotype-B) was covered with a lid having a hole (diameter about 5 mm) in the center. Make a notch with a width of about 5 mm in a circular filter paper with a diameter of 6.5 cm so that a strip-shaped filter paper piece is formed, and immerse the strip-shaped filter paper piece hanging downward from the hole in the lid into the water in the cup. And put cotton wool on the filter paper. In this way, three leaf discs (2 cm x 2 cm) cut out from the primary leaves of the common bean to lay eggs on cotton wool that is constantly replenished with water in the cup so that the number of eggs per disc is about 10 are placed. It was. Spawning was carried out by holding pot-planted common beans in a greenhouse where Bemisia tabaci is occurring for 24 hours. This cup was placed in an acrylic cylinder having a height of 50 cm and a diameter of 10 cm, and a water-diluted solution (500 ppm) of an emulsion prepared according to Formulation Example 1 was sprayed at 2.0 ml per cup using an airbrush. After spraying, it was kept in a constant temperature room at 25 ° C. Fourteen days after the treatment, the number of unhatched eggs and the state of the hatched larvae were observed under binoculars in three categories: survival, agony (non-walkable state), and death. Based on the observation results, the egg killing + larval rate (%) was calculated. The test was carried out by using 1 cup in each section.

Egg killing + larva rate (%) = (number of unhatched eggs + number of abnormal larvae + number of dead larvae) / number of test eggs x 100

As a result, compound numbers A-3, A-6, C-2, C-7, C-8, C-9, C-12, C-14, C-15, C-16, D-1, D The compound of the present invention of -3 showed an egg killing + larval rate of 90% or more. On the other hand, Comparative Agent A had an egg killing rate of 0% and a larval rate.

Claims

Equation (1),

[During the ceremony,
R 1 is C 1-6 alkyl group, C 1-6 haloalkyl group, C 2-6 alkenyl group, C 2-6 haloalkenyl group, C 2-6 alkynyl group, C 2-6 haloalkynyl group, C 3 -6 Cycloalkyl C 1-6 alkyl group or C 3-6 halocycloalkyl C 1-6 alkyl group,
n indicates an integer from 0 to 2
X is, C 1-6 alkyl, C 1-6 haloalkyl group, C 3-6 cycloalkyl alkyl groups, C 2-6 alkenyl groups, C 2-6 alkynyl group, C 2-6 haloalkenyl, C 2- 6 Haloalkynyl group, C 1-6 alkoxy group, C 1-6 haloalkoxy group, C 3-6 halocycloalkyl group, C 1-6 alkoxycarbonyl group, C 1-6 alkoxymethyl group, formyl group, halogen atom , Cyano group or nitro group,
Y represents a hydrogen atom, a halogen atom, a C 1-6 alkyl group or a C 1-6 haloalkyl group.
R 2a , R 2b , R 2c and R 2d may be the same or different, respectively, and represent a hydrogen atom, a halogen atom, a C 1-6 alkyl group or a C 1-6 haloalkyl group.
J 1 indicates direct binding, -CR 3a R 3b -or -CR 3a R 3b -CR 3c R 3d-
J 2 indicates direct binding or -CR 3e R 3f-
R 3a , R 3b , R 3c , R 3d , R 3e and R 3f may be the same or different, respectively, and represent a hydrogen atom, a halogen atom, a C 1-6 alkyl group or a C 1-6 haloalkyl group.
M indicates -CR 4a R 4b- , -NR 5- , -O-, -S-, -S (O)-or -S (O) 2- ,
R 4a and R 4b may be the same or different, respectively, and represent a hydrogen atom, a halogen atom, a C 1-6 alkyl group, a C 1-6 haloalkyl group, a cyano group or a C 1-6 alkoxycarbonyl group.
R 5 is a C 1-6 alkyl group, a C 1-6 haloalkyl group, a C 1-6 alkoxycarbonyl group, a C 1-6 alkylcarbonyl group, a C 1-6 haloalkylcarbonyl group, a C 1-6 alkylsulfonyl group or C 1-6 shows a haloalkylsulfonyl group. ]
1-Benzylamine derivative represented by, N-oxide thereof or a salt thereof.
Equation (2),

[During the ceremony,
R 1 is C 1-6 alkyl group, C 1-6 haloalkyl group, C 2-6 alkenyl group, C 2-6 haloalkenyl group, C 2-6 alkynyl group, C 2-6 haloalkynyl group, C 3 -6 Cycloalkyl C 1-6 alkyl group or C 3-6 halocycloalkyl C 1-6 alkyl group,
n indicates an integer from 0 to 2
X is, C 1-6 alkyl, C 1-6 haloalkyl group, C 3-6 cycloalkyl alkyl groups, C 2-6 alkenyl groups, C 2-6 alkynyl group, C 2-6 haloalkenyl, C 2- 6 Haloalkynyl group, C 1-6 alkoxy group, C 1-6 haloalkoxy group, C 3-6 halocycloalkyl group, C 1-6 alkoxycarbonyl group, C 1-6 alkoxymethyl group, formyl group, halogen atom , Cyano group or nitro group,
Y represents a hydrogen atom, a halogen atom, a C 1-6 alkyl group or a C 1-6 haloalkyl group.
R 6 and R 7 may be the same or different, hydrogen atom, C 1-6 alkyl group, C 1-6 haloalkyl group, cyano group, cyano C 1-6 alkyl group, C 2-6 alkenyl group, C. 2-6 alkynyl group, C 2-6 haloalkenyl group, C 2-6 haloalkynyl group, phenyl group optionally substituted with one or more with R 8 , C 1-3 alkylphenyl group (at this time, the phenyl group is , R 9 may be substituted one or more) or R 10 may be substituted one or more C 3-6 cycloalkyl groups.
R 8 represents a halogen atom, C 1-6 alkyl group or C 1-6 haloalkyl group.
R 9 represents a halogen atom, C 1-6 alkyl group or C 1-6 haloalkyl group.
R 10 represents a halogen atom, a C 1-6 alkyl group or a C 1-6 haloalkyl group. ]
1-Benzylamine derivative represented by, N-oxide thereof or a salt thereof.
The 1 -benzylamine derivative according to claim 1 or 2, an N-oxide thereof or a salt thereof, wherein R 1 represents a C 1-6 alkyl group or a C 1-6 haloalkyl group.
The 1-benzylamine derivative according to claim 1-2, an N-oxide thereof or a salt thereof, wherein X represents a C 1-6 alkyl group, a C 1-6 haloalkyl group, a halogen atom or a cyano group.
The 1-benzylamine derivative according to any one of claims 1 to 4, wherein n indicates 1, N-oxide or a salt thereof.
Equation (3),

[During the ceremony,
R 1 is C 1-6 alkyl group, C 1-6 haloalkyl group, C 2-6 alkenyl group, C 2-6 haloalkenyl group, C 2-6 alkynyl group, C 2-6 haloalkynyl group, C 3 -6 Cycloalkyl C 1-6 alkyl group or C 3-6 halocycloalkyl C 1-6 alkyl group,
n indicates an integer from 0 to 2
X is, C 1-6 alkyl, C 1-6 haloalkyl group, C 3-6 cycloalkyl alkyl groups, C 2-6 alkenyl groups, C 2-6 alkynyl group, C 2-6 haloalkenyl, C 2- 6 Haloalkynyl group, C 1-6 alkoxy group, C 1-6 haloalkoxy group, C 3-6 halocycloalkyl group, C 1-6 alkoxycarbonyl group, C 1-6 alkoxymethyl group, formyl group, halogen atom , Cyano group or nitro group,
Y represents a hydrogen atom, a halogen atom, a C 1-6 alkyl group or a C 1-6 haloalkyl group. ]
1-Benzyl alcohol derivative represented by.
Equation (1),

[In the formula, X, Y, n, R 1 , R 2a , R 2b , R 2c , R 2d , M, J 1 and J 2 are as defined in claim 1. ]
A method for producing a 1-benzylamine derivative represented by.
Equation (4),

[In the formula, X, Y, n and R 1 are as defined in claim 1. ]
Benzaldehyde derivative represented by
Equation (5),

[In the formula, R 2a , R 2b , R 2c , R 2d , M, J 1 and J 2 are as defined in claim 1. ]
A production method comprising reacting with an amine represented by (1) or a salt thereof.
Equation (2),

[In the formula, X, Y, n, R 1 , R 6 and R 7 are as defined in claim 2. ]
A method for producing a 1-benzylamine derivative represented by.
Equation (4),

[In the formula, X, Y, n and R 1 are as defined in claim 2. ]
Benzaldehyde derivative represented by
Equation (6),

[In the formula, R 6 and R 7 are as defined in claim 2. ]
A production method comprising reacting with an amine represented by (1) or a salt thereof.
Equation (3),

[In the formula, X, Y, n and R 1 are as defined in claim 6. ]
A method for producing a 1-benzyl alcohol derivative represented by.
Equation (4),

[In the formula, X, Y, n and R 1 are as defined in claim 1. ]
Benzaldehyde derivative represented by
A production method comprising reacting NaBH 4 , NaBH (OAc) 3 or NaBH 3 CN.
Equation (1),

[In the formula, X, Y, n, R 1 , R 2a , R 2b , R 2c , R 2d , M, J 1 and J 2 are as defined in claim 1. ]
A method for producing a 1-benzylamine derivative represented by.
Equation (7),

[During the ceremony,
R 1 is C 1-6 alkyl group, C 1-6 haloalkyl group, C 2-6 alkenyl group, C 2-6 haloalkenyl group, C 2-6 alkynyl group, C 2-6 haloalkynyl group, C 3 -6 Cycloalkyl C 1-6 alkyl group or C 3-6 halocycloalkyl C 1-6 alkyl group,
n indicates an integer from 0 to 2
X is, C 1-6 alkyl, C 1-6 haloalkyl group, C 3-6 cycloalkyl alkyl groups, C 2-6 alkenyl groups, C 2-6 alkynyl group, C 2-6 haloalkenyl, C 2- 6 Haloalkynyl group, C 1-6 alkoxy group, C 1-6 haloalkoxy group, C 3-6 halocycloalkyl group, C 1-6 alkoxycarbonyl group, C 1-6 alkoxymethyl group, formyl group, halogen atom , Cyano group or nitro group,
Y represents a hydrogen atom, a halogen atom, a C 1-6 alkyl group or a C 1-6 haloalkyl group.
Z represents a methanesulfonyl group or a trifluoromethanesulfonyl group. ]
And the compound represented by
Equation (5),

[In the formula, R 2a , R 2b , R 2c , R 2d , M, J 1 and J 2 are as defined in claim 1. ]
A production method comprising reacting with an amine represented by (1) or a salt thereof.
Equation (2),

[In the formula, X, Y, n, R 1 , R 6 and R 7 are as defined in claim 2. ]
A method for producing a 1-benzylamine derivative represented by.
Equation (7),

Wherein, R 1, n, X, Y and Z are as defined in claim 10. ]
And the compound represented by
Equation (6),

[In the formula, R 6 and R 7 are as defined in claim 2. ]
A production method comprising reacting with an amine represented by (1) or a salt thereof.
An agricultural and horticultural agent containing the 1-benzylamine derivative according to any one of claims 1 to 5, its N-oxide or a salt thereof.
A mite control agent for agriculture and horticulture containing the 1-benzylamine derivative according to any one of claims 1 to 5, N-oxide thereof or a salt thereof.
A nematode control agent for agriculture and horticulture containing the 1-benzylamine derivative according to any one of claims 1 to 5, its N-oxide or a salt thereof.
An agricultural and horticultural pest control agent containing the 1-benzylamine derivative according to any one of claims 1 to 5, its N-oxide or a salt thereof.
An agricultural and horticultural disease-preventing agent containing the 1-benzylamine derivative according to any one of claims 1 to 5, its N-oxide or a salt thereof.
A method for controlling plant pests, which comprises the step of treating pests and / or their habitat and / or seeds and / or plant breeding materials with the agricultural and horticultural chemicals according to claim 12.
A method for controlling pests of a plant, which comprises a step of treating a place where a useful crop is to be grown, a place where the crop is being grown, or a growing crop with the agricultural and horticultural agent according to claim 12. ..
A method for preparing a pesticide composition, which comprises a step of mixing a bulking agent and / or a surfactant with the agricultural and horticultural agent according to claim 12.