JP2022116370A - Novel 1-benzylamine derivative and agricultural and horticultural agents with the same as active ingredient - Google Patents

Abstract

To provide a compound useful as an agricultural and horticultural agents, in particular, a pest control agent for agriculture and horticulture, an acarid pest control agent, a nematode control agent or a disease control agent.SOLUTION: As an active ingredient, a 1-benzylamine derivative represented by the following formula (1) or (2), its N-oxide or its salt is blended.SELECTED DRAWING: None

Description

The present invention provides 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, an acaricide, a nematode control agent, or an agricultural and horticultural disease control agent and its It relates to usage.

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

US 2009/0082389 A1 JP 2014-108943 A WO2018/051252

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

[式中、
Ｒ¹は、Ｃ_1-6アルキル基、Ｃ_1-6ハロアルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6ハロアルケニル基、Ｃ_2-6アルキニル基、Ｃ_2-6ハロアルキニル基、Ｃ_3-6シクロアルキルＣ_1-6アルキル基又はＣ_3-6ハロシクロアルキルＣ_1-6アルキル基を示し、
nは、0～2の整数を示し、
Ｘは、Ｃ_1-6アルキル基、Ｃ_1-6ハロアルキル基、Ｃ_3-6シクロアルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6アルキニル基、Ｃ_2-6ハロアルケニル基、Ｃ_2-6ハロアルキニル基、Ｃ_1-6アルコキシ基、Ｃ_1-6ハロアルコキシ基、Ｃ_3-6ハロシクロアルキル基、Ｃ_1-6アルキコキシカルボニル基、Ｃ_1-6アルコキシメチル基、ホルミル基、ハロゲン原子、シアノ基又はニトロ基を示し、
Ｙは、水素原子、ハロゲン原子、Ｃ_1-6アルキル基又はＣ_1-6ハロアルキル基を示し、
Ｒ^2a、Ｒ^2b、Ｒ^2c及びＲ^2dは、それぞれ同一又は異なっても良く、水素原子、ハロゲン原子、Ｃ_1-6アルキル基又はＣ_1-6ハロアルキル基を示し、
Ｊ¹は、直結、ＣＲ^3aＲ^3b-又は-ＣＲ^3aＲ^3b-ＣＲ^3cＲ^3d-を示し、
Ｊ²は、直結又は-ＣＲ^3eＲ^3f-を示し、
Ｒ^3a、Ｒ^3b、Ｒ^3c、Ｒ^3d、Ｒ^3e及びＲ^3fは、それぞれ同一又は異なっても良く、水素原子、ハロゲン原子、Ｃ_1-6アルキル基又はＣ_1-6ハロアルキル基を示し、
Ｍは、-ＣＲ^4aＲ^4b-、-ＮＲ⁵-、-Ｏ-、-Ｓ-、-Ｓ(Ｏ)-又は-Ｓ(Ｏ)₂-を示し、
Ｒ^4a及びＲ^4bは、それぞれ同一又は異なっても良く、水素原子、ハロゲン原子、Ｃ_1-6アルキル基、Ｃ_1-6ハロアルキル基、シアノ基又はＣ_1-6アルコキシカルボニル基を示し、
Ｒ⁵は、Ｃ_1-6アルキル基、Ｃ_1-6ハロアルキル基、Ｃ_1-6アルコキシカルボニル基、Ｃ_1-6アルキルカルボニル基、Ｃ_1-6ハロアルキルカルボニル基、Ｃ_1-6アルキルスルホニル基又はＣ_1-6ハロアルキルスルホニル基を示す。]、又は As a result of intensive studies 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 an agricultural and horticultural agent, particularly an agricultural They have found that it is useful as a horticultural pest control agent, acaricide, nematode control agent or disease control agent, and completed the present invention.
That is, the present invention provides an agricultural and horticultural agent containing, as an active ingredient, a 1-benzylamine derivative represented by the following formula (1) or (2), an N-oxide thereof, or a salt thereof, a method for using the same, and the It relates to a manufacturing method.
Formula (1):

[In the formula,
R ¹ is a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _2-6 alkenyl group, a C _2-6 haloalkenyl group, a C _2-6 alkynyl group, a C _2-6 haloalkynyl group, and a C _{3 -6} cycloalkyl C _1-6 alkyl group or C _3-6 halocycloalkyl C _1-6 alkyl group,
n is an integer from 0 to 2,
X is a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _3-6 cycloalkyl group, a C _2-6 alkenyl group, a C _2-6 alkynyl group, a C _2-6 haloalkenyl group, a 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, represents a halogen atom, a cyano group or a 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 and represent a hydrogen atom, a halogen atom, a C _1-6 alkyl group or a C _1-6 haloalkyl group,
J ¹ represents a direct connection, CR ^3a R ^3b - or -CR ^3a R ^3b -CR ^3c R ^3d -,
J ² represents a direct connection or -CR ^3e R ^3f -,
R ^3a , R ^3b , R ^3c , R ^3d , R ^3e and R ^3f may be the same or different and represent a hydrogen atom, a halogen atom, a C _1-6 alkyl group or a C _1-6 haloalkyl group,
M represents ^-CR4aR4b- , ^-NR5- , -O-, -S-, -S ⁽ O)- or -S(O) _2- ,
R ^4a and R ^4b , which may be the same or different, each represents 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 It represents a C _1-6 haloalkylsulfonyl group. ], or

[式中、
Ｒ¹は、Ｃ_1-6アルキル基、Ｃ_1-6ハロアルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6ハロアルケニル基、Ｃ_2-6アルキニル基、Ｃ_2-6ハロアルキニル基、Ｃ_3-6シクロアルキルＣ_1-6アルキル基又はＣ_3-6ハロシクロアルキルＣ_1-6アルキル基を示し、
nは、0～2の整数を示し、
Ｘは、Ｃ_1-6アルキル基、Ｃ_1-6ハロアルキル基、Ｃ_3-6シクロアルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6アルキニル基、Ｃ_2-6ハロアルケニル基、Ｃ_2-6ハロアルキニル基、Ｃ_1-6アルコキシ基、Ｃ_1-6ハロアルコキシ基、Ｃ_3-6ハロシクロアルキル基、Ｃ_1-6アルキコキシカルボニル基、Ｃ_1-6アルコキシメチル基、ホルミル基、ハロゲン原子、シアノ基又はニトロ基を示し、
Ｙは、水素原子、ハロゲン原子、Ｃ_1-6アルキル基又はＣ_1-6ハロアルキル基を示し、
Ｒ⁶及びＲ⁷は、同一又は異なっても良く、水素原子、Ｃ_1-6アルキル基、Ｃ_1-6ハロアルキル基、シアノ基、シアノＣ_1-6アルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6アルキニル基、Ｃ_2-6ハロアルケニル基、Ｃ_2-6ハロアルキニル基、Ｒ⁸で１個以上置換されていてもよいフェニル基、Ｃ_1-3アルキルフェニル基（このときフェニル基はＲ⁹で１個以上置換されていてもよい）又はＲ¹⁰で１個以上置換されていてもよいＣ_3-6シクロアルキル基を示し,
Ｒ⁸は、ハロゲン原子、Ｃ_1-6アルキル基又はＣ_1-6ハロアルキル基を示し、
Ｒ⁹は、ハロゲン原子、Ｃ_1-6アルキル基又はＣ_1-6ハロアルキル基を示し、
Ｒ¹⁰は、ハロゲン原子、Ｃ_1-6アルキル基又はＣ_1-6ハロアルキル基を示す。]。 Formula (2):

[In the formula,
R ¹ is a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _2-6 alkenyl group, a C _2-6 haloalkenyl group, a C _2-6 alkynyl group, a C _2-6 haloalkynyl group, and a C _{3 -6} cycloalkyl C _1-6 alkyl group or C _3-6 halocycloalkyl C _1-6 alkyl group,
n is an integer from 0 to 2,
X is a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _3-6 cycloalkyl group, a C _2-6 alkenyl group, a C _2-6 alkynyl group, a C _2-6 haloalkenyl group, a 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, represents a halogen atom, a cyano group or a 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 R ⁸ groups, C _1-3 alkylphenyl group (wherein the phenyl group is optionally substituted with one or more R ⁹ ) or a C _3-6 cycloalkyl group optionally substituted with one or more R ¹⁰ ,
R ⁸ represents a halogen atom, a C _1-6 alkyl group or a C _1-6 haloalkyl group,
R ⁹ represents a halogen atom, a C _1-6 alkyl group or a 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 exhibits excellent effects as an agricultural and horticultural agent, particularly as an agricultural and horticultural pest control agent, acaricide, nematode control agent or disease control agent. It is also effective against pests parasitic on pet animals such as dogs and cats, or livestock such as cattle 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 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 linear or branched alkyl group having 1 to 6, preferably 1 to 3 carbon atoms such as group, tert-pentyl group, n-hexyl group, isohexyl group, and "C _1-6 haloalkyl ” means 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” means , for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like are cyclic cycloalkyl groups having 3 to 6 carbon atoms, preferably 3 to 4 carbon atoms.

Examples of C _1-6 haloalkyl groups include fluoromethyl, chloromethyl, difluoromethyl, trifluoromethyl, chlorodifluoromethyl, bromodifluoromethyl, dichlorofluoromethyl, 1-fluoroethyl, 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 linear or branched alkyl groups having 1 to 6 carbon atoms substituted with 1 to 9, preferably 3 to 9 halogen atoms such as groups.
The C _2-6 alkenyl group includes, for example, vinyl group, allyl group, isopropenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-pentenyl group, 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 2 to 6, preferably 2 to 4 straight-chain or branched alkenyl groups are included.
C _2-6 haloalkenyl groups include, for example, 1-fluorovinyl group, 2-fluorovinyl group, 2,2-difluorovinyl group, 3-chloro-2-propenyl group, 3,3-difluoro-2-allyl group, 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- C2-6 straight chain substituted with 1 to 9, preferably 2 to 5 halogen atoms having at least one double bond at any position, such as fluoro-2-hexenyl group or a branched alkenyl group.

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

Examples of C _1-6 haloalkoxy groups include fluoromethoxy, dichloromethoxy, trichloromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, dichlorofluoromethoxy, 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 and the like, preferably 1 to 9 and a straight-chain or branched-chain alkoxy group having 1 to 6 carbon atoms substituted with a halogen atom.
C _3-6 halocycloalkyl groups include, for example, 1-fluorocyclopropyl, 2-fluorocyclopropyl, 2,2-difluorocyclopropyl, 2,2,3,3-tetrafluorocyclopropyl, 1-chlorocyclopropyl 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 2 , 2-dichlorocyclopentyl and 1-fluorocyclohexyl groups, preferably cycloalkyl groups having 3 to 6 carbon atoms substituted with 1 to 4 halogen atoms.

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. Preferred carbon numbers of the C _3-6 cycloalkyl group and the C _1-6 alkyl group constituting the C _3-6 cycloalkyl C _1-6 alkyl group are the same as defined above.
Examples of C _3-6 halocycloalkyl C _1-6 alkyl groups include 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 Groups such as butylmethyl, 3,3-difluorocyclopentylmethyl, 3,3-dichlorocyclopentylmethyl, 4,4-difluorocyclohexylmethyl or 4,4-dichlorocyclohexylmethyl may be mentioned. The number of halogen atoms in the C _3-6 halocycloalkyl group constituting the C _3-6 halocycloalkyl C _1-6 alkyl group, and the preferable number of carbon atoms in the C _3-6 halocycloalkyl group and the C _1-6 alkyl group are as above.

Examples of C _1-6 alkoxycarbonyl groups include groups such as methoxycarbonyl, ethoxycarbonyl, n-propylcarbonyl, n-butylcarbonyl, n-pentylcarbonyl, n-hexylcarbonyl and i-propylcarbonyl groups. The preferred number of carbon atoms in the C _1-6 alkoxy group constituting the C _1-6 alkoxycarbonyl group is as described above.
The content of the C _1-6 alkoxy group in the C _1-6 alkoxymethyl group is as explained above.
The content of the C _1-6 alkyl group in the C _1-6 alkylcarbonyl group is as explained above.
The content of the C _1-6 haloalkyl group in the C _1-6 haloalkylcarbonyl group is as described above.
The content of the C _1-6 alkyl group in the C _1-6 alkylsulfonyl group is as explained above.
The content of the C _1-6 haloalkyl group in the 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 hydrochloride, sulfate, nitrate and phosphate, acetate and fumarate. , maleates, oxalates, methanesulfonates, benzenesulfonates, p-toluenesulfonates and the like.
The 1-benzylamine derivative represented by the formula (1) or (2) of the present invention may contain one or more asymmetric centers in its structural formula, and has two or more optical isomers. and diastereomers may exist, and the present invention includes all optical isomers and mixtures containing them in any ratio. In addition, the 1-benzylamine derivative represented by the formula (1) or (2) of the present invention may have two geometric isomers derived from a carbon-carbon double bond in its structure. However, the present invention also includes all geometric isomers and mixtures thereof in any proportion.

[式中、Ｘ、Ｙ及びＲ¹は、式(１)で定義した通りである。]
反応式１に示す方法においては、前記式（９）で表される3-スルフィニルベンズアルデヒド誘導体は、前記式（８）で表される3-スルファニルベンズアルデヒド誘導体の酸化反応により製造することができる。 Representative methods for producing the novel 1-benzylamine derivative represented by the formula (1) or (2) of the present invention are shown below, but the present invention is not limited thereto.
Reaction formula 1

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

As the solvent used in the oxidation reaction of the 3-sulfanylbenzaldehyde compound represented by formula (8), a wide range of solvents inert to the reaction can be used. For example, aliphatic or alicyclic hydrocarbon solvents such as hexane, cyclohexane, and heptane; aromatic hydrocarbon solvents such as benzene, chlorobenzene, toluene, and xylene; and halogenated solvents such as 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, propio Examples include nitrile solvents such as nitrile, aprotic polar solvents such as N-methylpyrrolidone and N,N'-dimethylimidazolinone, carboxylic acids such as acetic acid, and water. One of these solvents can be used alone, or two or more of them can be used in combination, if necessary.
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, hypochlorous acid tert- butyl, sodium hypochlorite and the like.
Such an oxidizing agent can be used in an amount of generally 1 to 3 equivalents, preferably 1 to 2.5 equivalents, relative to the 3-sulfanylbenzaldehyde derivative represented by formula (8).
The reaction can usually be carried out at -78°C to the boiling point of the solvent used, preferably at 0°C to room temperature.
Although the reaction time varies depending on the reaction temperature and other factors, it cannot be generalized, 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 commonly used isolation means such as organic solvent extraction, chromatography, recrystallization, distillation, etc. 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 the method described in known literature, for example, Molecules. 2015, 20, 5409-5422.

[式中、Ｘ、Ｙ、n、Ｒ¹、Ｒ^2a、Ｒ^2b、Ｒ^2c、Ｒ^2d、Ｍ、Ｊ¹及びＪ²は、式(１)で定義した通りである。］
反応式２に示す反応においては、前記式（１）で表される1-ベンジルアミン誘導体は、前記式（４）で表されるベンズアルデヒド誘導体と前記式（５）で表されるアミン類とを、還元剤の存在下に不活性溶媒中で反応させることにより製造することができる。 Reaction formula 2

[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). ]
In the reaction shown in Reaction Scheme 2, the 1-benzylamine derivative represented by the above formula (1) reacts with the benzaldehyde derivative represented by the above formula (4) and the amines represented by the above 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 formula (4) and the compound of formula (5), a wide range of solvents inert to the reaction can be used. For example, aliphatic or alicyclic hydrocarbon solvents such as hexane, cyclohexane, and heptane; aromatic hydrocarbon solvents such as benzene, chlorobenzene, toluene, and xylene; and halogenated solvents such as methylene chloride, 1,2-dichloroethane, and chloroform. Hydrocarbon solvents, ether solvents such as diethyl ether, tetrahydrofuran, and 1,4-dioxane, ester solvents such as methyl acetate and ethyl acetate, alcohol solvents such as methanol, ethanol, propanol, and isopropanol, acetic acid, formic acid, and propion. Carboxylic acid solvents such as acids, amide solvents such as N,N-dimethylformamide, nitrile solvents such as acetonitrile and propionitrile, aprotic polar solvents 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 them can be used in combination, if necessary. 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 formula (4) and the compound of formula (5), known borohydride compounds and salts thereof, or aluminum hydride compounds can be used. Examples of borohydride compounds and salts thereof include borane, borane-tetrahydrofuran complex, borane-2-methylpyridine complex, sodium borohydride, sodium cyanoborohydride, sodium triacetoxyborohydride and the like. Examples of aluminum hydride compounds include lithium aluminum hydride and diisopropyl aluminum hydride.
Such a reducing agent can be used in an amount of generally 1 to 100 equivalents, preferably 1 to 2 equivalents, relative to the benzaldehyde compound represented by the formula (4).
As for the proportion of the benzaldehyde compound represented by the formula (4) and the amine represented by the formula (5), it is more preferable to use 1 to 2 moles of (5) to (4).
The reaction can usually be carried out at -78°C to the boiling point of the solvent used, preferably at room temperature to 100°C.
Although the reaction time varies depending on the reaction temperature and the like, it cannot be generalized, 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 commonly used isolation means such as organic solvent extraction, chromatography, recrystallization, distillation, etc. Further, it can be purified by ordinary purification means.

[式中、Ｘ、Ｙ、n、Ｒ⁶及びＲ⁷は、式(２)で定義した通りである。］
反応式３に示す反応においては、前記式（２）で表される１－ベンジルアミン誘導体は、前記式（４）で表されるベンズアルデヒド誘導体と、前記式（６）で表されるアミン類とを、還元剤の存在下に不活性溶媒中で反応させることにより製造することができる。 Reaction formula 3

[In the formula, X, Y, n, R ⁶ and R ⁷ are as defined in formula (2). ]
In the reaction shown in Reaction Scheme 3, the 1-benzylamine derivative represented by the above formula (2) is combined with the benzaldehyde derivative represented by the above formula (4) and the amines represented by the above formula (6). can be prepared by reacting in an inert solvent in the presence of a reducing agent.

As the solvent used in the reaction between the compound of formula (4) and the compound of formula (6), a wide range of solvents inert to the reaction can be used. For example, aliphatic or alicyclic hydrocarbon solvents such as hexane, cyclohexane, and heptane; aromatic hydrocarbon solvents such as benzene, chlorobenzene, toluene, and xylene; and halogenated solvents such as methylene chloride, 1,2-dichloroethane, and chloroform. Hydrocarbon solvents, ether solvents such as diethyl ether, tetrahydrofuran, and 1,4-dioxane, ester solvents such as methyl acetate and ethyl acetate, alcohol solvents such as methanol, ethanol, propanol, and isopropanol, acetic acid, formic acid, and propion. Carboxylic acid solvents such as acids, amide solvents such as N,N-dimethylformamide, nitrile solvents such as acetonitrile and propionitrile, aprotic polar solvents 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 them can be used in combination, if necessary. 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 formula (4) and the compound of formula (6), known borohydride compounds and salts thereof, or aluminum hydride compounds can be used. Examples of borohydride compounds and salts thereof include borane, borane-tetrahydrofuran complex, borane-2-methylpyridine complex, sodium borohydride, sodium cyanoborohydride, sodium triacetoxyborohydride and the like. Aluminum hydride compounds include lithium aluminum hydride and diisopropyl aluminum hydride.
Such a reducing agent can be used in an amount of generally 1 to 100 equivalents, preferably 1 to 2 equivalents, relative to the benzaldehyde compound represented by the formula (4).
The proportion of the benzaldehyde compound represented by the formula (4) and the amine represented by the formula (6) is 1 to 2 moles 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 at -78°C to the boiling point of the solvent used, preferably at room temperature to 100°C.
Although the reaction time varies depending on the reaction temperature and other factors, it cannot be generalized, 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 commonly used isolation means such as organic solvent extraction, chromatography, recrystallization, distillation, and the like. , can be further purified by conventional purification means.

[式中、
Ｒ¹は、Ｃ_1-6アルキル基、Ｃ_1-6ハロアルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6ハロアルケニル基、Ｃ_2-6アルキニル基、Ｃ_2-6ハロアルキニル基、Ｃ_3-6シクロアルキルＣ_1-6アルキル基又はＣ_3-6ハロシクロアルキルＣ_1-6アルキル基を示し、
nは、0～2の整数を示し、
Ｘは、Ｃ_1-6アルキル基、Ｃ_1-6ハロアルキル基、Ｃ_3-6シクロアルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6アルキニル基、Ｃ_2-6ハロアルケニル基、Ｃ_2-6ハロアルキニル基、Ｃ_1-6アルコキシ基、Ｃ_1-6ハロアルコキシ基、Ｃ_3-6ハロシクロアルキル基、Ｃ_1-6アルコキシカルボニル基、Ｃ_1-6アルコキシメチル基、ホルミル基、ハロゲン原子、シアノ基又はニトロ基を示し、
Ｙは、水素原子、ハロゲン原子、Ｃ_1-6アルキル基又はＣ_1-6ハロアルキル基を示す。]
反応式４に示す反応においては、前記式（３）で表される１－ベンジルアルコール誘導体は、前記式（４）で表されるベンズアルデヒド誘導体と、NaBH₄、NaBH(OAc)₃又はNaBH₃CNとを不活性溶媒中で反応させることにより製造することができる。 Reaction formula 4

[In the formula,
R ¹ is a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _2-6 alkenyl group, a C _2-6 haloalkenyl group, a C _2-6 alkynyl group, a C _2-6 haloalkynyl group, and a C _{3 -6} cycloalkyl C _1-6 alkyl group or C _3-6 halocycloalkyl C _1-6 alkyl group,
n is an integer from 0 to 2,
X is a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _3-6 cycloalkyl group, a C _2-6 alkenyl group, a C _2-6 alkynyl group, a C _2-6 haloalkenyl group, a C _{2- 6} haloalkynyl group, _C1-6 alkoxy group, _C1-6 haloalkoxy group, C3-6 _{halocycloalkyl} group, _C1-6 alkoxycarbonyl group, _C1-6 alkoxymethyl group, formyl group, halogen atom , represents a cyano group or a nitro group,
Y represents a hydrogen atom, a halogen atom, a _C1-6 alkyl group or a _C1-6 haloalkyl group. ]
In the reaction shown in Reaction Scheme 4, the 1-benzyl alcohol derivative represented by the above formula (3) is a benzaldehyde derivative represented by the above formula (4) and NaBH ₄ , NaBH(OAc) ₃ or NaBH ₃ CN can be produced by reacting with in an inert solvent.

As the solvent used in the reaction of the compound of formula (4) with NaBH ₄ , NaBH(OAc) ₃ or NaBH ₃ CN, a wide range of solvents inert to the reaction can be used. For example, aliphatic or alicyclic hydrocarbon solvents such as hexane, cyclohexane, and heptane; aromatic hydrocarbon solvents such as benzene, chlorobenzene, toluene, and xylene; and halogenated solvents such as methylene chloride, 1,2-dichloroethane, and chloroform. Hydrocarbon solvents, ether solvents such as diethyl ether, tetrahydrofuran, and 1,4-dioxane, ester solvents such as methyl acetate and ethyl acetate, alcohol solvents such as methanol, ethanol, propanol, and isopropanol, acetic acid, formic acid, propion Carboxylic acid solvents such as acids, amide solvents such as N,N-dimethylformamide, nitrile solvents such as acetonitrile and propionitrile, aprotic polar solvents 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 them can be used in combination, if necessary.
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 formula (3). can be used in quantity.
The reaction can usually be carried out at -78°C to the boiling point of the solvent used, preferably at room temperature to 100°C.
Although the reaction time varies depending on the reaction temperature and other factors, it cannot be generalized, 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 commonly used isolation means such as organic solvent extraction, chromatography, recrystallization, and distillation. , can be further purified by conventional purification means.

[式中、Ｘ、Ｙ、n、Ｒ¹、Ｒ^2a、Ｒ^2b、Ｒ^2c、Ｒ^2d、Ｍ、Ｊ¹及びＪ²は、式(1)で定義した通りであり、Ｚは、メタンスルホニル基又はトリフルオロメタンスルホニル基を示す。］
反応式５に示す反応においては、前記式（７）で表される化合物は、前記式（３）で表されるベンジルアルコール誘導体と、メタンスルホニルクロリド又はトリフルオロメタンスルホニルクロリドを、トリエチルアミン等の塩基の存在下、ジクロロメタン等の不活性溶媒中で反応させることにより製造することができる。
また、前記式（１）で表されるベンジルアミン誘導体は、前記式（７）で表される化合物と式（５）で表されるアミン類とを適切な塩基の存在下、不活性溶媒中で反応させることにより製造することができる。 Reaction formula 5

[Wherein, 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), Z is methanesulfonyl group or trifluoromethanesulfonyl group. ]
In the reaction shown in Reaction Scheme 5, the compound represented by Formula (7) is obtained by combining the benzyl alcohol derivative represented by Formula (3) and methanesulfonyl chloride or trifluoromethanesulfonyl chloride with 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) can be obtained by combining the compound represented by the formula (7) and the amine represented by the formula (5) in the presence of an appropriate base in an inert solvent. It can be produced by reacting with

As the solvent used in the reaction between the compound of formula (7) and the compound of formula (5), a wide range of solvents inert to the reaction can be used. For example, aliphatic or alicyclic hydrocarbon solvents such as hexane, cyclohexane, and heptane; aromatic hydrocarbon solvents such as benzene, chlorobenzene, toluene, and xylene; and halogenated solvents such as methylene chloride, 1,2-dichloroethane, and chloroform. Hydrocarbon solvents, ether solvents such as diethyl ether, tetrahydrofuran, and 1,4-dioxane, ester solvents such as methyl acetate and ethyl acetate, alcohol solvents such as methanol, ethanol, propanol, and isopropanol, acetic acid, formic acid, propion Carboxylic acid solvents such as acids, amide solvents such as N,N-dimethylformamide, nitrile solvents such as acetonitrile and propionitrile, aprotic polar solvents 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 them can be used in combination, if necessary.
Examples of the base used in the reaction between the compound represented by the formula (7) and the amine represented by the formula (5) include potassium carbonate, cesium carbonate, oily sodium hydride, sodium hydroxide, Triethylamine and the like are preferred.
The ratio of the base used in the reaction between the compound represented by the formula (7) and the amine represented by the formula (5) is 1 to 2 times the amount of the base relative to the compound represented by the formula (7). It is more preferred to use molar amounts.
The reaction can usually be carried out at -78°C to the boiling point of the solvent used, preferably at room temperature to 100°C.
Although the reaction time varies depending on the reaction temperature and other factors, it cannot be generalized, 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 commonly used isolation means such as organic solvent extraction, chromatography, recrystallization, distillation, etc. Further, it can be purified by ordinary purification means.

[式中、Ｘ、Ｙ、n、Ｒ⁶及びＲ⁷は、式(２)で定義した通りであり、Ｚは、メタンスルホニル基又はトリフルオロメタンスルホニル基を示す。］
反応式６に示す反応においては、前記式（７）で表される化合物は、前記式（３）で表されるベンジルアルコール誘導体と、メタンスルホニルクロリド又はトリフルオロメタンスルホニルクロリドとを、トリエチルアミン等の塩基の存在下、ジクロロメタン等の不活性溶媒中で反応させることにより製造することができる。
また、前記式（２）で表される１－ベンジルアミン誘導体は、前記式（７）で表される化合物と式（６）で表されるアミン類とを適切な塩基の存在下、不活性溶媒中で反応させることにより製造することができる。 Reaction formula 6

[In the formula, X, Y, n, R ⁶ and R ⁷ are as defined in formula (2), and Z represents a methanesulfonyl group or a trifluoromethanesulfonyl group. ]
In the reaction shown in Reaction Scheme 6, the compound represented by Formula (7) is obtained by combining the benzyl alcohol derivative represented by Formula (3), methanesulfonyl chloride or trifluoromethanesulfonyl chloride with a base such as triethylamine. 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) is an inactive compound represented by the formula (7) and the amine 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 formula (7) and the compound of formula (6), a wide range of solvents inert to the reaction can be used. For example, aliphatic or alicyclic hydrocarbon solvents such as hexane, cyclohexane, and heptane; aromatic hydrocarbon solvents such as benzene, chlorobenzene, toluene, and xylene; and halogenated solvents such as methylene chloride, 1,2-dichloroethane, and chloroform. Hydrocarbon solvents, ether solvents such as diethyl ether, tetrahydrofuran, and 1,4-dioxane, ester solvents such as methyl acetate and ethyl acetate, alcohol solvents such as methanol, ethanol, propanol, and isopropanol, acetic acid, formic acid, propion Carboxylic acid solvents such as acids, amide solvents such as N,N-dimethylformamide, nitrile solvents such as acetonitrile and propionitrile, aprotic polar solvents 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 them can be used in combination, if necessary.
Examples of the base used in the reaction between the compound represented by the formula (7) and the amine represented by the formula (6) include potassium carbonate, cesium carbonate, oily sodium hydride, sodium hydroxide, or Triethylamine and the like are preferred.
The ratio of the base used in the reaction between the compound represented by the formula (7) and the amine represented by the formula (6) is 1 to 2 times the mole of the base relative to the compound of the formula (7). It is more preferable to use quantity.
The reaction can usually be carried out at -78°C to the boiling point of the solvent used, preferably at room temperature to 100°C.
Although the reaction time varies depending on the reaction temperature and other factors, it cannot be generalized, 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 commonly used isolation means such as organic solvent extraction, chromatography, recrystallization, distillation, and the like. , can be further purified by conventional purification means.

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

表1

General formula (1)

table 1

表２

Table 2

表３

Table 3

表４

general formula (2)

Table 4

Representative compounds of 1-benzyl alcohols represented by the formula (3) are shown in Table 5, but the present invention is not limited thereto.
The physical properties in the table indicate properties and melting point (° C.), "n-" indicates normal, "s-" indicates secondary, "t-" indicates tertiary, and "i-" indicates iso, "Me" represents a methyl group, "Et" represents an ethyl group, "Pr" represents a propyl group, "Bu" represents a butyl group, and "Ph" represents a phenyl group.

表５

general formula (3)

Table 5

Representative compounds of benzaldehydes represented by the formula (4) are shown in Table 6, but the present invention is not limited to these.
The physical properties in the table indicate properties and melting point (° C.), "n-" indicates normal, "s-" indicates secondary, "t-" indicates tertiary, and "i-" indicates iso, "Me" represents a methyl group, "Et" represents an ethyl group, "Pr" represents a propyl group, "Bu" represents a butyl group, and "Ph" represents a phenyl group.

表６

general formula (4)

Table 6

The compounds of the present invention can be used for the prevention or control of harmful organisms in agriculture, indoors or forests, on livestock or in a variety of situations such as hygiene. Specific usage scenes, target pests, and usage methods are shown below, but the content of the present invention is not limited to these.
The compound of the present invention can be used in crops such as food crops (rice, barley, wheat, rye, barley such as oats, corn, potato, sweet potato, taro, soybean, adzuki bean, broad bean, pea, kidney bean, peanut, etc.). beans, etc.), vegetables (cabbage, Chinese cabbage, radish, turnip, broccoli, cauliflower, cruciferous crops such as Komatsuna, pumpkin, cucumber, watermelon, melon, melon, eggplant, tomato, green pepper, pepper , okra, spinach, lettuce, lotus root, carrot, burdock, garlic, onion, green onions, etc.), mushrooms (shiitake mushrooms, mushrooms, etc.), fruit trees and fruits (apples, citrus fruits, pears, grapes, peaches, plums) , cherries, walnuts, chestnuts, almonds, bananas, strawberries, etc.), fragrances and other ornamental crops (lavender, rosemary, thyme, parsley, pepper, ginger, etc.), special crops (tobacco, tea, sugar beet, sugarcane, hops, cotton, hemp, olives, rubber, coffee, etc.), pasture and feed crops (timothy, clover, alfalfa, corn, sorghum, orchardgrass, gramineous grass, leguminous grass, etc.), lawns (Korai grass, bentgrass, etc.) ), forest trees (Todomatsu, Ezo spruce, pines, hiba, cedar, cypress, etc.) and ornamental plants (herbaceous and flowering plants such as chrysanthemums, roses, carnations, orchids, garden trees such as ginkgo, cherry blossoms, Aoki, etc.) It can also be used to control pests such as arthropods, mollusks, nematodes, and fungi such as the phyla Mycophyta, Mycophyta, Bacteria, and Actinomycota, as well as bacteria, which cause damage to . Specific pests include the following.

Lepidoptera of the phylum Arthropoda Insecta, for example Helicoverpa armigera of the family Noctuidae, Heliothis spp., Agrotis segetum, Autographa nigrisigna, Trichoplusia ni ), Mamestra brassicae, Spodoptera exigua, Spodoptera litura, etc., Plutella xylostella, etc. of the sedge family, Adoxophyes orana fasciata, Adoxophyes honmai), Archips fuscocupreanus, Homona magnanima, Caloptilia theivora, Grapholita molesta, Eumeta minuscula, etc., Lyonetia prunifoliella malinella), Lyonetia clerkella, etc., Phyllocnistis citrella, etc., Phyllonorycter ringoniella, etc., Acrolepiopsis sapporensis, etc., Synantedin hector, etc. , Stathmopoda masinissa, etc., Pectinophora gossypiella, etc., Carposina niponensis, etc., Cossus jezoensis, etc., Nemapogon granella, etc. , Monema flavecens, Parasa lepida, Scopelodes con tracus), etc., Chilo suppressalis of the Tsutoga family, Scirpophaga incertulas, Cnaphalocrocis medialis, Hellulla undalis, Conogethes punctiferlis, Diaphania indica, Shibattoga (Parapediasia teterrella), etc., Locastra muscosalis, etc.

Parnara guttata, etc. of the family Papilio xuthus, etc., Pieris rapae crucivora, etc. of the family Pieris rapae crucivora, Lampides boeticus, etc. of the family Lycaenidae, Ascotis selenaria of the Geometridae family Etc., Shrimp Sparrow (Agrius convolvuli), etc., Phalera flavescens, etc., Phalera flavescens, etc., Malacosoma neustrium testaceum, etc., Saturnia japonica, etc. (Euproctis pseudoconspersa) Orgyia thyellina, Telochurus recens approximans, etc., Spilosoma imparilis, Hyphantria cunea, etc., Grapeberry moss (Endopiza viteana), Codling moth (Laspeyresia) pomonella), etc., adults, larvae and eggs;

Coleoptera, for example, Anomala cuprea, Popillia japonica, Oxycetonia jucunda, Anomala geniculata, etc. of Scarabaeidae, Agrilus auriventris of Buprestidae, etc. , Melanotus fortnumi, etc., Epilachna vigintioctopunctata, Epilachna vigintioctopunctata, Anoplophora malasiaca, Xylotrechus pyrrhoderus, etc. Aulacophora femoralis), Rootworm species (Diabrotica spp.), Phyllotreta striolata, Cassida nebulosa, Phaedon brassicae, Oulema oryzae, Mexican beetle (Epilachna varivestis), Colorado potato beetle (Leptinotarsa decemlineata) ), etc., Rhynchites heroes, etc., Cylas formicarius, etc., Curculio sikkimensis, Lissorhoptrus oryzophilus, Boll weevil (Anthonomus gradis grandis), Sphenophrus venatus vestitus, etc., adults, larvae and eggs such as Epuraea domina of the family Pelargonium;

Heteroptera of the order Hemiptera, such as Eurydema rugosum, Eysarcoris lewisi, Eysarcoris parvus, Nezara viridula, Germania Stink bug (Plautia stali), brown stink bug (Halymorpha mista), etc., pear stink bug (Urochela luteovoria), etc. , Cletus punctiger, etc., Leptocorisa chinensis, etc., Dysdeercus cingulatus, etc., Stephanitis nashi, Stephanitis pyrioides etc., adults, larvae, and eggs such as Apolygus spinolai (Apolygus spinolai), Stenotus rubrovittalus, Trigonotylus coelestialium (Trigonotylus coelestialium), etc.

Homoptera of the order Hemiptera, such as Platypleura kaempferi of the family Cicada, Arboridia apicalis of the family Leafhopper, Empoasca onukii, Nephotettix cincticeps , Nephotettix virescens, etc., Laodelphax striatellus, Nilaparvata lugens, Sogatella furcifera, etc., Geisha distinctissima pyrus, etc., Psyllasisuga, Psyllasisuga Citrus whitefly (Diaphorina citri), etc., Aleurocanthus spiniferus of the family Whitefly, various biotypes of silver leaf whitefly (Bemisia argentifolii), tobacco whitefly (Bemisia tabaci), orange whitefly (Dialeurodes citri), whitefly (Trialeurodes vaporariorum), etc. , Grape aphid (Viteus vitifolii) of the Phylloxera family, etc.

Aphis citricola, Aphis craccivora, Aphis gossypii, Aulacorthum solani, Brevicoryne brassicae, Toxoptera aurantii, Aphid citrus (Toxoptera citricidus), elder aphid (Aulacorthum magnoliae), pear aphid (Schizaphis piricola), pear aphid (Nippolachnus piri), radish aphid (Lipaphis erysimi), peach aphid (Hyalopterus pruni), Aphid Aphis ( Pleotrichophorus chrysanthemi), Macrosiphoniella sanborni, Megoura crassicauda, Sitobion ibarae, Macrosiphum euphorbiae, Myzus varians, Myzus persica ), Rhopalosiphum rufiabdominalis, Rhopalosiphum padi, Sitobion akebiae, Eriosoma lanigerum, Icerya purchasi, etc. Pseudococcus comstocki, Phenacoccus viburnae, Phenacoccus kraunhiae, etc., Ceroplastes ceriferus, Ceroplastes rubens, etc. (Aonidiell a aurantii), pear scale (Comstockaspis perniciosa), mulberry scale (Pseudaulacaspis pentagoa), and unaspis scale (Unaspis yanonensis) adults, larvae and eggs;

Thysanoptera, for example Scirtothrips dorsalis of the family Thrips, Thrips palmi, Thrips tabaci, Thrips setosus, Frankliniella intonsa, citrus Adults, larvae and eggs of Frankliniella occidentalis, Heliothrips haemorrhoidalis, etc., Ponticulothrips diospyrosi, Haplothrips aculeatus, etc. of the family Thrips family;

Hymenoptera, for example, Athalia rosae ruficornis, Arge pagana, etc., Arge mali, etc., Dryocsmus kuriphilus, etc. Adults and larvae such as Megachile nipponica nipponica, Formica japonica, Camponotus kiusiuensis, Lasius fuliginosus, Solenopsis richteri, S. invicta, S. geminata, etc. and eggs;
Diptera, for example, Asphondylia yushimai of the family Asphondylia, Rhacochlaena japonica of the family Tephritidae, Bactrocera cucurbitae, etc., Hydrellia griseola of the family Drosophila, etc. Drosophila suzukii, etc., Liriomyza trifolii, Liriomyza sativae, Chromatomyia horticola, Agromyza oryzae, Liriomyza bryoniae, etc. Adults, larvae and eggs such as Delia platura and Delia antiqua;

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

Adults, larvae and eggs of the order Collembola of the phylum Arthropod Insecta, such as Sminthurus viridis of the family Sminthurus viridis, and Onychiurus matsumotoi of the family Shirotobimidae; Adults, larvae and eggs of the class Isopada, such as Armadillidium vulgare of the family Armadillidium vulgare;
Acari of the phylum Arachnidae, for example, Polyphagotarsonemus latus, Phytonemus pallidus, etc., Penthaleus major, etc., Brevipalpus lewisi), Brevipalpus phoenicis, etc., Panonychus citri, Panonychus ulmi, Tetranychus urticae, Tetranychus kanzawai, Amphitetranychus viennensis, Totomatsuno spider mite ( Oligonychus ununguis, Bryobia eharai, Eotetranychus kankitus, Bryobia praetiosa, etc., Aculus Schlechtendali, Aculops pelekassi, Phyllocoptruta citri ), Eriophyes chibaensis, Aceria tulipae, Colomerus vitis, Aculus fockeui, Calacarus carinatus, Tyrophagus putrescentiae, Rhizoglyphus robini), etc., adults, larvae and eggs;

Architaenioglossa of the phylum Gastropoda Molluscs, for example, Pomacea canaliculata of the genus Pomacea canaliculata, Plumonata, for example, Achatina fulica of the family Achatina fulica, of the slug family Slug (Meghimatium bilineatum), Milax gagates of the family Slug family, Chakoura slug of the family Slug family (Lehmannina valentiana), Acusta despecta sieboldiana of the family Acusta despecta sieboldiana, etc.;
Tylenchida of the order Nematoda Phantomia, for example, Ditylenchus destructor of the family Anguinidae, Tylenchorhynchus claytoni of the family Tylenchorhynchus, etc., Pratylenchus penetrans of the family Platylenchus ), Pratylenchus coffeae, etc., Helicotylenchus dihystera, etc. of the family Helicotylenchus dihystera, etc., Globodera rostochiensis of the family Globodera, Meloidogyne incognita of the family Meloidogyne, etc. Nematodes (Criconema jaejuense), etc., Strawberry Nematodes (Nothotylenchus acris) of the family Anguinaceae, etc., Strawberry Nematodes (Aphelecchoides fragarriae) of the family Aphelenkoides, etc.; .), Trichodorus sp., etc.;
Fungi and bacteria such as Eumycota, Myxomycota, Bacteriomycota, and Actinomycota.

Diseases to which the compounds of the present invention can be applied include, specifically, rice blast (Pyricularia oryzae), sesame leaf blight (Cochliobolus miyabeanus), sheath blight (Rhizoctonia solani), and brown spot disease (Pantoe ananatis). ), Acidovorax avene subsp. avenae, Pseudomonas fuscovaginae, Xanthomonas oryzae pv. oryzae, Burkholderia plantarii, etc.; graminis), Fusarium head blight (Gibberella zeae), Fusarium head blight (Puccinia striiformis, P.graminis, P. recondita, P. hordei), Snow rot (Typhula sp. , Micronectriella nivalis), Naked smut (Ustilago tritici, U nuda), Tilletia caries, Pseudocercosporella herpotrichoides, Rhynchosporium secalis, Septoria tritici, Leptosphaeria nodorum, Pyrenophora teres , hail (Helminthosporium zonatum Ikata), black blight (Pseudomonas syringae pv. japonica), etc.; , brown rot (Phytophthora citrophthora, P. nicotianae), scab (Phyllosticta citricarpa), etc.; Alternaria mali), black spot (Venturia inaequalis), black spot (My cospherella pomi), anthracnose (Colletotrichum acutatum), ring blight (Botryosphaeria berengeriana), red star disease (Gymnosporangium yamadae), ash star disease (Monilinia fructicola), etc.;

Pear scab (Venturia nashicola, V. pirina), Black spot (Alternaria kikuchiana), Gymnosporangium haraeanum, Ash star (Monilinia fructigena), etc.; Cladosporium carpophilum), Phomopsis sp. , Brenneria nigrifluens, etc.; Elsinoe ampelina, Colletotrichum acutatum, Uncinula necator, Rust ( Phakopsora ampelopsidis, Guignardia bidwellii, Plasmopara viticola, Monilinia fructigena, Cladosporium viticolum, Botrytis cinerea, (Agrobacterium vitis), etc.; Gloeosporium kaki of oysters, Cercospora kaki, Mycoshaerella nawae, etc.; Colletotrichum lagenarium, powdery mildew (Sphaerotheca fuliginea, Oidiopsis taurica), vines Blight (Didymella bryoniae), Fusarium oxysporum, Downy mildew (Pseudoperonospora cubensis), Late blight (Phytophthora sp.), Seedling blight (Pythium sp.), etc.; lochrymans), Pseudomonas viridiflava, Xanthomonas campestris pv. cucurbitae, etc.; Xanthomonas campestris pv. disease (St reptomyces sp.), etc.; Watermelon fruit spot bacterial disease (Acidovorax avenae pv. citrulli), etc.;

Solanaceous vegetable wilt (Ralstonia solanacearum), etc.; tomato ring spot (Alternaria solani), leaf mold (Cladosporium fulvum), late blight (Phytophthora infestans), mildew (Clavibacter michiganense subsp. Pseudomonas corrugata, Pectobacterium carotovorum subsp. carotovorum, etc.; Phomopsis vexans, powdery mildew (Erysiphe cichoracearum), etc.; Alternaria japonica, white spot of cruciferous vegetables (Cercosporella brassicae) Soft rot (Pectobacterium carotovorum subsp. carotovorum), etc.; Cabbage rot (Pseudomonas syringae pv. marginalis), Black rot (Xanthomonas campestris pv. campestris), etc.; , Bacterial spot disease (Xanthomonas campestris pv. vitians), green onion rust (Puccinia allii), etc.; soybean purpura (Cercospora kikuchii), black spot (Elsinoe glycines), black spot (Diaporthe phaseolorum var. sojae), etc.; Bean anthracnose (Colletotrichum lindemthianum), etc.; black rot (Cercospora personata), brown spot (Cercospora arachidicola), etc.; pea powdery mildew (Erysiphe pisi), etc.; summer plague of potatoes (Alternaria) solani), late blight (Phytophthora infestans), leaf rot (Rhizoctonia solani), etc.; strawberry powdery mildew (Sphaerotheca humuli), etc.; tea net blast (Exobasidium reticulatum), white star disease ( Elsinoe leucospira), Pseudomonas syringae pv. theae, Canker disease (Xanthomonas campestris pv. theicola), etc.;

Tobacco red star (Alternaria longipes), powdery mildew (Erysiphe cichoracearum), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacina), late blight (Phytophthora nicotianae), damping off (Ralstonia solanacearum), cavity disease ( Pectobacterium carotovorum subsp. carotovorum), etc.; Cercospora beticola of sugar beets, Aphanomyces cochliodes, etc.; Diplocarpon rosae, powdery mildew (Sphaerotheca pannosa), etc.; disease (Septoria chrysanthemi-indici), white rust (Puccinia horiana), root canker disease (Agrobacterium tumefaciens), etc.; Sclerotinia sclerotiorum) ; lawn snow rot (Pythium iwayamai, Tyohula incarnate, Fusarium nivale, Sclerotinia borealis), powdery mildew (Erysiphe graminis), Falling disease (Lycoperdon perlatum, Lepista subnudo, Marasmius oreades), pseudo leaf rot (Ceratobasidium spp.), Take-off (Gaemannomyces graminis), Curvularia geniculata, Leaf rot (Rhizoctonia solani), Pythium periplocum, Pythium vanterpoolii, Rust (Puccinia spp.), Dollar spot disease (Sclerotinia homoeocarpa), etc.; bentgrass red scorch (Pythium aphanidermatum) and anthracnose (Colletotrichum sp.).

The compound of the present invention is active indoors in buildings including general houses, and damages or decomposes wood and its processed products such as wooden furniture, stored food, 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 Arthropoda Insecta, such as Coptotermes formosanus, Reticulitermes speratus, other Reticulitermes hesperus, R. tibialis, R. flavipes, R. lucifugus, R. santonensis, etc.), Incisitermes minor, Odontotermes formosanus, Hodotermopsis jzponica, Cryptotermes adult, larvae and Cryptotermes domesticus egg;
Coleoptera, for example, Sitophilus zeamais, Sitophilus zeamais, etc., Sitophilus zeamais, Callosobruchus chinensis, Bruchus pisorum, Bruchus rufimanus, etc. Tribolium castaneum, Tribolium confusum, etc., Oryzaephilus surinamensis, Cryptolestes pusillus, etc., Lasioderma serricorne, Jinsan (Stegobium paniceum), etc., Attagenus unicolor japonicus, Anthrenus verbasci, Dermestes maculatus, Gibbium aequinnoctiale, etc. Dinoderus minutus, Rhizopertha dominica, etc. Adults, larvae and eggs such as Lyctus brunneus of the family Lyctus brunneus;

Lepidoptera, for example, Cadra cautella, Ephestia kuehniella, Plodia interpunctella, etc., Sitotroga cerealella, etc., Tinea translucens), Tineola bisselliella, and other adults, larvae, and eggs;
Adults, larvae and eggs such as Cockroaches, such as Cockroach (Blattella germanica), Cockroach (Periplaneta fuliginosa), Yamato Cockroach (Periplaneta japonica); pharaoni), monomorium nipponense, etc. adults, larvae and eggs;

Adults, larvae and eggs such as Ctenolepisma villosa, Lepisma saccharina, etc.
Adults, larvae and eggs of Diptera, such as Drosophila melangogaster of the family Drosophila, Piophila casei of the family Cheesefly, etc.;
Adults, larvae and eggs of Carpoglyphus lactis of the family Carpoglyphus;
Fungal wood-rotting fungi Tyromyces palustris, Coriolus versicolor, etc.;
Aspergillus niger, Aspergillus terreus, Aureobasidium pullulans, Chaetomium globosum, Cladosporium cladosporioides, Eurotium tonophilus, Fusarium moniliforme, Gliocladium virens, Myrothecium verrucaria, Penicillium citrinum, Penicillium funiculosum, Rhizopus oryzae, etc., which are degrading microorganisms of materials.

The compounds of the present invention can also be used to control pests that damage or weaken trees in natural forests, artificial forests and urban green spaces. Specific pests include the following.

Lepidoptera of the phylum Arthropoda Insecta, for example, Calliteara argentata, Euproctis pseudoconspersa, Orygia recens approximans, Euproctis subflava, Lymantria dispar, etc. Malacosoma neustria testacea, Dendrolimus spectabilis, Dendrolimus superans, etc., Crytoblabes loxiella, etc., Agrotis segetum, etc. (Ptycholoma lecheana circumclusana), Cydia kurokoi, Cydia cryptomeriae, etc., Spilosoma imparilis, Hyphantria cunea, etc., Stigmella castanopsiella, etc. Adults, larvae and eggs of Parasa lepida, Scopelodes contracus, Microleon longipalpis, etc.; Agrilus spinipennis of the family, etc., Monochamus alternatus of the family Longhorn beetle, etc., Basilepta pallidula of the family Chrysomelidae, etc., Scepticus griseus of the weevil family, Shirahoshizo insidiosus ), etc., Sipalinus gigas, etc., of the family Barkworm (Tomicus piniperda), Indocryphalu s aceris), etc., adults, larvae and eggs such as Rhizopertha dominica of the family Rhizopertha;

Stink bugs, for example, Cinara todocola of the family Aphididae, Adelges japonicus of the family Aphididae, etc., Aspidiotus cryptomeriae of the family Aspidiotus, etc., Ceroplastes of the family ceriferus), adults, larvae and eggs;
Hymenoptera, for example Pachynematus itoi of the family Sawfly, etc., Neodiprion sertifer of the family Pine bee, etc. Adults, larvae and eggs of Dryocosmus kuriohilus of the family Bee, etc.; Adults, larvae, and eggs such as Tipula aino, etc., Strobilomyia laricicola, etc., Contarinia inouyei, Contarinia matsusintome, etc.;
Adults, larvae and eggs such as Oligonichus hondoensis and Oligonichus ununguis of Acarina of the phylum Arachnid of Arthropoda;
Nematozoa Phantomia Tylenx order, for example, Bursaphelenchus xylophilus of the family Parasitapherencidae.

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

Diptera of the phylum Arthropoda Insecta, for example, Tabanus rufidens, Tabanus chrysurus, etc., Musca bezzii, Musca domestica, Stomoxys calcitrans, etc. Gasterophilus intestinalis, etc., Hypoderma bovis, etc., Oestrus ovis, etc., Aldrichina grahami, etc., Megaselia spiracularis, etc. Etc., Sepsis punctum, etc., Telmatoscopus albipunctatus, Psychoda alternata, etc., Culex pipiens molestus, Culex pipiens pallens , Anopheles sinensis, Culex pipiens triaeniorhynchus summorosus, Ades albopictus, etc., Simulium iwatense, Prosimulium yezoense, etc., Culicoides schulzei, Chicken midge ( Culicoides arakawae) and other adults, larvae and eggs;
Adults, larvae and eggs of the order Fleas, for example Pulex irritans of the family Pulex irritans, Ctenocephalides canis, etc.;

Louses, for example, pig lice (Haematopinidae suis) of the family Haematopinidae, bovine lice (Haematopinidae eurysternus), etc., horse lice (Damalinia bovis), etc. Adults, larvae and eggs such as (Menopon gallinae);
Acarina of the phylum Arachnid of the phylum Arthropoda, for example Varroa jacobsoni of the family Varroa jacobsoni, Haemaphysalis longicornis of the family Ixodidae, Ixodes ovatus, Boophilus microplus, Amblyomma testudinarium), Ornithonyssus sylvialum, etc., Dermanyssus gallinae, etc., Demodex phylloides, etc.

Adults, larvae and eggs such as Otodectes cynotis and Psoroptes communis of the family Sarcoptes scabiei bovis and Knemidocoptes mutans;
Nematoda Bilinear cocterodila, such as bovine hookworm, pig kidneyworm, pig lungworm, hairy nematode, bovine tuberculosis, etc.:
Ascaris order, for example, pig roundworm, chicken roundworm, etc.;
Platyhelminthe fluke, for example, Schistosoma japonicum, Liver tetsu, Deer doublet fluke, Westermann lung fluke, Japanese chicken egg fluke, etc.;
Taenia, for example, tapeworms, tapeworms, tapeworms, tapeworms, benedene tapeworms, tapeworms, tapeworms, ring tapeworms, etc.:
Rhizomastigotes of the Protozoa phylum Flagellata, for example, Histomonas, etc., Protoflagellates, for example, Leishmania, Trypanosoma, etc., Polymastigotes, for example, Giardia, etc. Trichomonads, for example, Trichomonas, etc.:
Amoeba of the Sarcophyte class, such as Entamoeba;
Subclass Piroplasma of the class Sporozoa, such as Theilaria, Babesia, etc., Subclass Latex, such as Eimeria, Plasmodium, Toxoplasma, etc.

The compounds of the invention can also be used to control pests that cause direct human harm or discomfort, or to maintain public health conditions against pests that carry or transmit pathogens. Specific pests include the following.

Lepidoptera of the phylum Arthropoda Insecta, for example, Sphrageidus similis of the family Sphageidus similis, Kunugia undans of the family Coleoptera, Parasa consocia of the family Parasa consocia, Artona martini adults, larvae and eggs, etc.;
Coleoptera, for example, Xanthochroa waterhousei of the family Longhornidae, etc., Epicauta gohani of the family Blister beetle, etc. Adults, larvae, and eggs of Paederus fuscipes, etc.;
Hymenoptera, for example Vespa simillima xanthoptera of the family Vespa simillima xanthoptera, etc., Brachyponera chinensis of the family Ant family, adults, larvae and eggs of the family Batozonellus annulatus, etc.;
Diptera, for example, Armigeres subalbatus of Mosquito family, Culicoides nipponensis of Culicoides family, Chironomus yoshimatsui of Chironomidae family, Simulium nikkoense of Blackfly family, etc. such as Hirosia humilis of the family Housefly (Musca domestica), etc., Fannia canicularis of the family Himefly (Fannia canicularis), etc. adults, larvae and eggs;

Adults, larvae and eggs of the order Fleas, e.g. Pulex irritans of the family Pulex irritans;
Adults, larvae and eggs such as Cockroaches, for example, Blattella germanica of the German cockroach family, Periplaneta americana of the Cockroach family, Periplaneta americana, Black cockroach (Periplaneta fuliginosa), Yamato cockroach (Periplaneta japonica);
Adults, larvae and eggs such as Orthoptera (Orthoptera), for example, Diestrammena japonica and Diestrmmena apicalis of the family Cologgiidae;
Adults, larvae and eggs of the order of the order of the Louse family, such as Pediculus humanus humanus, Phthirius pubis;
Adults, larvae and eggs of Isyndus obscurus of the family Reduviidae, such as Cimex lectularius of the family Cimexidae;

Adults, larvae and eggs of the order Collembola of the phylum Arthropod Insecta, such as the Hypogastrura communis of the family Boraginidae;
Acarina of the phylum Arachnididae, for example, Ixodes persulcatus of the family Tick family, Ornithonyssus bacoti of the family Ornithonyssus bacoti, etc., Chelacaropsis moorei of the family Chelacaropsis moorei, etc., Pyemotes of the family Pyemotes Ventricosus), Demodex folliculorum, etc., Dermotophagoides pteronyssinus, etc., Sarcoptes scabiei, etc. Adults, larvae, and eggs of Trombicula akamushi, etc. ;
Eleganea, for example, Chiracanthium japonicum, etc. of the family Osmanthidae, Heteropoda venatoria, etc., Spermophora senoculata, Pholcus phalangioides, etc., Uroctea compactilis, etc. ), adults, larvae and eggs such as Plexippus paykulli and Plexippus adansoni of the family Jumping Spider;

Adults, larvae and eggs of the Scorpion order, e.g. Isometrus europaeus of the family Arctic Scorpion;
Adults, larvae and eggs such as Scolopendra subspinipes mutilans and Scolopendra subspinipes japonica of the family Scolopendra subspinipes mutilans;
Adults, larvae and eggs, such as the order of the Lagoonia order, for example, Thereuronema hilgendofi of the family Lapisaceae;
Adults, larvae and eggs such as Oxidus gracilis of the family Oxidus gracilis;
Adults, larvae and eggs of the order Isopoda of the phylum Crustacea of the phylum Arthropoda, for example Porcellio scaber of the family Woodlouse;
Annelids of the Phylum Verrucosa, for example, Yamabiru (Haemadipsa zeylanica japonica) of the family Yamabiru, etc.;
Trichophyton rubrum, Trichophyton mentagrophytes, etc., which are trichophyton fungi, Candida albicans, etc., which are candida fungi, Aspergillus fumigatus, etc., fungi such as Aspergillus fumigatus, Escherichia coli, Gram-negative bacteria such as Pseudomonas aeruginosa, Staphylococcus aureus Gram-positive bacteria such as aureus and the like.

The compounds of the invention are of particular value in controlling pests such as arthropods, gastropods, nematodes, fungi that damage crops and trees and ornamental plants in natural and planted forests as well as urban green spaces. be. In such situations, the compounds of the present invention, in their commercially useful formulations and use forms prepared by those formulations, can be combined with other active compounds such as insecticides, acaricides, nematicides, fungicides. It can also be present as an admixture with agents, synergists, plant regulators, baits or herbicides.
Usable forms include wettable powders, wettable granules, dry flowables, water solutions, emulsions, liquids, oils, water suspensions, water emulsions and other flowables, capsules, powders, granules, and fine powders. It can take granules, baits, tablets, sprays, aerosols, aerosols and the like. In order to obtain these dosage forms, various pesticide adjuvants conventionally used in the technical field of agricultural and horticultural agents can be used as appropriate. Such an agricultural chemical adjuvant can be used, for example, for the purpose of improving the effects of agricultural and horticultural agents, stabilizing them, and improving their dispersibility.

Agrochemical adjuvants include, for example, carriers (diluents), emulsifiers, wetting agents, dispersants, disintegrants and the like. Liquid carriers 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 dimethylsulfoxide, and methylnaphthalene. , cyclohexane, animal and vegetable oils, fatty acids, and the like. As solid carriers, clay, kaolin, talc, diatomaceous earth, silica, calcium carbonate, montmorillonite, bentonite, feldspar, quartz, alumina, sawdust, nitrocellulose, starch, gum arabic and the like can be used.
Usual surfactants can be used as emulsifiers and dispersants, 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.
In addition, wetting agents such as dialkyl sulfosuccinate; sticking agents such as carboxymethylcellulose and polyvinyl alcohol; disintegrating agents such as sodium ligninsulfonate and sodium lauryl sulfate.
Of course, one or a combination of two or more of the compounds of the present invention can be blended as an active ingredient. The content of the compound of the present invention as an active ingredient in these formulations 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. Although it may be determined appropriately according to various conditions, for example, about 0.5 to 20% by mass, preferably 1 to 10% by mass for powders, and about 1 to 90% by mass, preferably 10% for wettable powders. ~80% by mass, and in the case of an emulsion, about 1~90% by mass, preferably 10~40% by mass, of the active ingredient.

For the control of arthropods, gastropods, nematodes and fungi, foliage of plants is usually applied to areas where damage by these pests is occurring or is likely to occur. In addition to spraying on the soil, it can be applied to the soil, etc. by applying it to the soil, etc., such as mixing all layers of the soil, applying it to the soil, applying it to the bed soil, treating the cell seedling, treating the planting hole, treating the root of the plant, top dressing, treating the box of rice, applying it to the surface of the water, etc. It can also be used by absorbing from It can also be used by immersing seeds in chemicals, seed dressing, seed treatment such as Culper treatment, application to nutrient solution in nutrient solution (hydroponics) cultivation, smoking or trunk injection. When used, it varies depending on the type and amount of pests, the type of target crops/trees, cultivation mode, and growth conditions, but in general, the amount of active ingredient is 0.1 to 1000 g, preferably 1 to 100 g, per 10 ares. apply. In order to process this, wettable powders, wettable granules, dry flowables, water solutions, emulsions, liquids, water suspensions, water emulsions and other flowables, capsules, etc. should be diluted with water, Although it varies depending on the type of target plant, cultivation mode, and growth state, it is generally sufficient to spray crops at an application rate of 10 to 1,000 liters per 10 ares. In the case of powders, sprays, or aerosols, crops or the like may be treated in the form of the formulation.
When the target pests mainly damage plants in the soil, or when the target pests are controlled by absorbing the chemical from the roots, for example, the formulation is diluted with water or not diluted. method of applying to the root of the plant or the nursery for raising seedlings, etc., method of spraying granules to the root of the plant or the nursery for raising seedlings, powder, wettable powder, water granules before sowing or transplanting A method of spraying blends, granules, etc. and mixing them with the entire soil, powders, wettable powders, wettable granules, granules, fine granules, etc. in planting holes, rows, etc. before sowing or planting plants, and the like. Wettable powders, water dispersible granules, water solutions, emulsions, liquids, suspensions in water, emulsions in water, and other flowable agents, capsules, etc. are diluted with water. In the case of powders, granules, fine granules, baits, etc., the formulations can be spread evenly over the entire area to be treated. It should be sprayed on the soil surface as much as possible. Spraying or irrigation may be done around seeds or crops/trees to be protected from damage. Tillage may also be applied during or after application to mechanically disperse the active ingredient.

As for the method of application to nursery boxes for paddy rice, the dosage form may differ depending on the application period, such as application at the time of sowing, application during the greening period, and application at the time of transplantation. It may be applied in a dosage form such as granules. It can also be applied by mixing with potting soil, and mixing potting soil with powders, wettable granules, granules or fine granules, for example, mixing with bed soil, mixing with covering soil, mixing with the whole potting soil, etc. can. Alternatively, the soil and various formulations may simply be layered alternately and applied.
As a method of application to paddy fields, solid formulations such as jumbo formulations, pack formulations, granules and wettable granules, and liquid formulations such as flowables and emulsions are usually sprayed over flooded paddy fields. In addition, at the time of rice planting, an appropriate formulation can be sprayed or injected into the soil as it is or mixed with fertilizer or the like. In addition, by using chemical solutions such as emulsions and flowables at water outlets, irrigation systems, and other sources of water inflow into paddy fields, it is possible to apply the chemicals in a labor-saving manner along with water supply.
Seed treatment methods include, for example, a method of immersing seeds in a liquid state with or without diluting a liquid or solid formulation to adhere and permeate the drug, mixing a solid or liquid formulation with seeds, Examples include a method of applying the powder to the surface of the seed by powder coating, a method of coating the seed by mixing with an adhesive carrier such as a resin or polymer, and a method of spraying near the seed at the same time as planting. The "seed" to be subjected to the seed treatment means a plant body in the early stage of cultivation used for plant propagation. Plants for propagation can be mentioned. In addition, the "soil" or "cultivation carrier" of plants when applied refers to a support for cultivating crops, particularly a support for growing roots, and the material is not particularly limited, but the plant Any material can be used as long as it can grow, and so-called soil, seedling mat, water, etc. may be used. rock wool, glass wool, wood chips, bark and the like.
As for the sowing of cultivated plants to be transplanted and the treatment during the seedling-raising period, in addition to the direct treatment of the seeds, irrigation of liquid chemicals or spraying of granules onto the nursery bed for raising seedlings is preferable. In addition, it is also preferable to apply granules to the planting holes at the time of planting or to mix them with cultivation carriers in the vicinity of the place of transplantation.

The compounds of the present invention are also of value in protecting wood (standing, fallen, processed, stored or structural wood) from damage by insects such as termites or coleoptera, fungi and the like. In such a situation, it is possible to control the wood or the soil around it by spraying, injecting, irrigating, or coating with oil, emulsion, wettable powder, or sol, or by spraying powder, granules, etc. can. Also, the oils, emulsions, wettable powders, powders, etc. used in this context may be mixed with other active compounds such as insecticides, acaricides, nematicides, fungicides, repellents or synergists. In these formulations, the total amount of active ingredient compounds is 0.0001 to 95% by mass, preferably 0.005 to 10% by mass for oil solutions, powders and granules, emulsions, wettable powders and sols. can be contained in an amount of 0.01 to 50% by mass. When controlling arthropods, fungi, etc., 0.01 to 100 g of the active ingredient compound per 1 m ² is sprayed on the soil or wood surface.

The compounds of the present invention are effective against Lepidoptera, Coleoptera, Acaridae and Mites when products such as cereals, fruits, nuts, spices and tobacco are stored as is, powdered or mixed in products. It can be used to protect against damage such as fungi. Animal products (skins, wool, wool and feathers, etc.) and plant products (cotton, paper, etc.) are also protected from attack by Lepidoptera, Coleoptera, Spots and Cockroaches when stored in their natural or transformed state. It can also protect against attack by Lepidoptera, Coleoptera, Flies and Mites when storing foods such as meat and fish. In such situations, spraying oil solutions, emulsions, wettable powders, powders, etc., installing resin transpiration agents, etc., treating fumigants and aerosols, installing granules, tablets and poison baits, spraying aerosols, etc. can be prevented by These formulations can also be present as admixtures with other active compounds such as insecticides, acaricides, nematicides, fungicides, repellents or synergists, in these formulations can contain 0.0001 to 95% by mass of active ingredient compounds in total.

The compounds of the present invention can spread arthropods and fungi that parasitize the body surface of humans and livestock and cause direct harm such as skin feeding or blood sucking, diseases of humans and livestock, or diseases such as such diseases. of arthropods, nematodes, flukes, tapeworms, protozoa, and arthropods that are annoying to humans. In such situations, the compounds of the present invention may be incorporated in small amounts in food or feed, or in suitable orally ingestible compounded pharmaceutical compositions, such as tablets, pills, and the like, containing pharmaceutically acceptable carriers and coating materials. Capsules, pastes, gels, beverages, medicated feeds, medicated drinking water, medicated feeds, slow-release large pills, other slow-release devices designed to be retained in the gastrointestinal tract, etc. Orally administered, or as sprays, powders, It can be administered transdermally as greases, creams, ointments, emulsions, lotions, spot-ons, pour-ons, shampoos and the like. In order to achieve effects in such applications, the formulation generally contains 0.0001 to 0.1% by mass, preferably 0.001 to 0.01% by mass, of the active ingredient compound. As a method of transdermal or topical administration, a device (eg, collar, medallion, ear tag, etc.) attached to the animal for local or systemic control of arthropods can also be used.

Specific oral administration methods and transdermal administration methods when the compound of the present invention is used as an antiparasitic agent for animals such as domestic animals and pets, or humans are shown, but are not necessarily limited to these.
When administered orally as a medicated drink, the drink is usually dissolved, suspended or dispersed in a suitable non-toxic solvent or water with suspending or wetting agents such as bentonite or other excipients. be. Beverages generally also contain an antifoaming agent. Beverage formulations generally contain 0.01-1.0%, preferably 0.01-0.1% by weight of active compound.
When it is desired to administer orally in a dry solid unit dose form, capsules, pills or tablets usually containing predetermined amounts of the active ingredient are employed. These use forms are obtained by intimately blending the active ingredient with suitable finely divided diluents, fillers, disintegrants and/or binders such as starch, lactose, talc, magnesium stearate, vegetable gums and the like. manufactured. Such unit dose formulations can vary widely in mass and content of anthelmintic agent depending on the species of host animal to be treated, the degree of infection and type of parasite and the body weight of the host.

When administered via animal feed, it can be dispersed homogeneously in the feed, used as a top dressing or used in the form of pellets. Usually 0.0001 to 0.05%, preferably 0.0005 to 0.01% by weight of the active ingredient compound is included in the final feed to achieve the desired antiparasitic effect.
Dissolved or dispersed in a liquid carrier vehicle, they can be administered to animals parenterally by intraforestomatric, 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 from 0.05 to 50% by weight of active compound, preferably from 0.1 to 5.0% by weight.
It can also be administered topically by mixing with a suitable carrier such as dimethylsulfoxide or a hydrocarbon solvent. The formulation is applied directly to the external surface of the animal by spraying or direct pouring.
The compounds of the present invention are also useful as anthelmintic agents for arthropods that directly harm them or arthropods that act as disease vectors against the surrounding environment where these pests may harbor. , spraying, injection, irrigation, coating of emulsions, wettable powders, etc., spraying of powders, etc., fumigants, heated aerosols such as mosquito coils, self-combustion fumigants, chemically reactive aerosols, fogging, etc. Treatment of fumigants, ULV agents, etc., installation of granules, tablets and poisonous baits, or addition of floating powders, granules, etc. by dropping into waterways, wells, reservoirs, water tanks and other running or standing water. You can also use it. In addition, it is possible to control Houttuynia cordata, etc., which are agricultural and forest pests, in the same manner as described above. It is also effective to use an electric mosquito trap to volatilize the mosquitoes into the air. It should be noted that these use forms formulations can also be present as admixtures with other active compounds such as pesticides, acaricides, nematodes, disease controllers, repellents or synergists. , the total amount of active ingredient compounds contained in these preparations is 0.0001 to 95% by mass.

The compounds of the invention can also exist as admixtures with other active compounds. Especially for controlling pests such as arthropods, gastropods, and nematodes that damage plants when used in combination with compounds (insecticides) having pest control activity, mite control activity or nematode control activity On the other hand, it becomes possible to expand the pests to be controlled, and a synergistic effect such as a reduction in the amount of chemicals can be expected. Specific examples of active compounds include the following.

organophosphorus agents such as acephate, azinphos-methyl, chlorpyrifos, daizinon, dichlorvos, dimeton-S-methyl, dimethoate, dimethylvinphos, disulfoton, ethion, fenitrothion, fenthion, isoxathion, malathion, methamidophos, methidathion, monocrotophos ( monocrotophos, naled, oxideprofos, parathion, phenthoate, phosalone, pirimiphos-methyl, piridafenthion, profenofos, prothiofos ), propaphos, pyraclofos, salition, sulprofos, thiometon, tetrachlorvinfos, trichlorphon, vamidothion, etc.;
Carbamates, such as alanycarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, furatiocarb (furathiocarb), isoprocarb, methomyl, metolcarb, pirimicarb, propoxur, thiodicarb, etc.;
organochlorine agents such as aldrin, chlordane, DDT (p,p'-DDT), endosulfan, lindane, etc.;

Pyrethroid agents such as acrinathrin, allethrin, bifenthrin, cycloprothrin, cyfluthrin, cyhalothrin, cyphenothrin, cypermethrin, deltamethrin ( deltamethrin, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flufenprox, fluvalinate, furamethrin, halofen halfenprox, imiprothrin, permethrin, phenothrin, prallethrin, pyrethrins, resmethrin, silafluofen, tefluthrin, tralomethrin, trans transfluthrin, etc.;

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

nereistoxin agents such as bensultap, cartap, thiocyclam, thiosultap, etc.;
Insect growth regulators such as phenylbenzoyl ureas and diacylhydrazines, e.g. chlorfluazuron, diflubenzuron, flufenoxuron, hexaflumuron, lufenuron, novaluron (novaluron), teflubenzuron, triflumuron, buprofezin, chromafenozide, halofenozide, methoxyfenozide, tebufenozide, cyromazine, etc.;
Juvenile hormone agents such as diofenolan, fenoxycarb, hydroprene, metoprene, pyriproxyfen, etc.;

insecticidal substances produced by microorganisms, such as abamectin, emamectin-benzoate, ivermectin, lepimectin, milbemectin, nemadectin, Nikkomycin , polyoxin complex (polioxin), spinetram (spinetram), spinosad (spinosad), BT agents, etc.;
Naturally derived insecticidal substances, such as anabasine, azadiractin, deguelin, decanolyoctanoylglycerol, hydroxypropyl starch, soybean lecithin, nicotine ), nornicotine, oreic acid sodium salt, petroleum oil, propylene glycol monolaurate, rape oil, rotenone, sorbitan fatty acid ester ( Sorbitan fatty acid ester), starch, etc.;

Other insecticides such as aphidpyropen, benzpyrimoxan, broflanilide, chlorfenapyr, diafenthiuron, dicloromezotiaz, dimpropyridaz ), DBEDC (dodecylbenzenesulphonic acidbisethylenediamine copper [II] salt), flonicamid, flometoquin, flufenerim, flupyradifurone, flupyrimin, fluralaner, fluhexafon, fluxametamide ( fluxametamide, hydramethylnon, indoxacarb, isocycloseram, metaflumizone, metaldehyde, nicotin sulfate, oxazosulfyl, pymetrozine, pyridalyl, pyrifluquinqzon, spirotetramat, sulfoxaflor, tolfenpyrad, triazamate, triflumezopyrim, tyclopyrazoflor )etc;

Acaricides such as acequinocyl, acinonapyr, amidoflumet, amitraz, azocyclotin, benzoximate, bifenazate, binapacryl, phenisobromo bromopropylate, chinomethionat, clofentezine, cyenopyrafen, cyflumetofen, cyhexatin, dicofol, dienochlor, ethoxazole , fenazaflor, fenazaquin, fenbutatin oxide, fenothiocarb, fenpyroximate, fluacrypyrim, hexythiazox, pirimidifen, polynactins, propargite, pyflubumide, pyridaben, spirodiclofen, spiropidion, spiromesifen, tebufenpyrad, tetradifon and KUI-1821 )etc:

Nematicides such as aluminum phosphide, benclothiaz, cadusafos, ethoprophos, fluazaindolizine, fluensulfone, fosthiazate, furfural ( furfural, imicyafos, levamisol hydrochloride, mesulfenfos, metam-ammonium, methyl isothiocyanate, morantel tartrate, oxamyl, thioxazafen, etc. ;
Poison baits such as chlorphacinone, coumatetralyl, diphacinone, sodium fluoracetate, warfarin, and the like.

The compounds of the invention may also be present as admixtures with other active compounds other than those having pesticidal, acaricidal or nematicidal activity. In order to control diseases and / or weeds that occur at the same time during the use period, by using it in combination with a compound having fungicidal activity, herbicidal activity or plant growth regulating activity, it is possible to reduce control effort and reduce the amount of medicine. A synergistic effect can also be expected. In addition, when used in combination with repellents, synergists, etc., a more effective control effect such as a synergistic effect can be expected.

Specific examples of active compounds include disease control agents such as
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, calcium polysulfide, captafol ( captafol, captan, carbendazim, carboxin, carpropamid, chinomethionat, chlorfenazole, chloroneb, chloropicrin, chlorothalonil , chlozolinate, DBEDC (complex of bis(ethylenediamine)copper-bis-(dodecylbenzenesulfonic acid)), copper hydroxide,

copper nonylphenol sulfonate, copper oxychloride, cyazofamid, cyflufenamid, cymoxanil, cyproconazole, cyprodinil, dazomet , diclobutrazol, dichlofluanid, dichlone, diclocymet, diclomezine, diethofencarb, difenoconazole, diflumetorim, dimethomorph , dimoxystrobin, diniconazole, diniconazole-M, dithane-stainless, dithianon, dodine, eclomezole, edifenphos ), enestrobin, epoxiconazole, etaconazole, ethaboxam, extract from mushroom, famoxadone, fenamidone, fenarimol, fenbuconazole, fenfuram, fenhexamid, fenoxanol, fenpiclonil, fenpropidin, fenpyrazamine, ferimzone, fluazinam ), flumetover, flumorph, fluopicolide, fluopyram, flu fluoroimide, fluotrimazole, fluoxastrobin,

fluquinconazole, flusulfamide, flutolanil, fluxapyroxad, folpet, fosetyl-AL, fthalide, fuberidazole, fludioxonil fludioxonil, flusilazole, flutianil, flutriafol, furametpyr, fluconazole, guazatine, hexaconazole, hydroxyioxazole , hymexazol, imazalil, imazalil sulfate, imibenconazole, iminoctadine acetate, iminoctadine-DBS, ipconazole, IBP (iprobenfos), iprodione, iprovalicarb, isofetamid, isoprothiolane, isopyrazam, isotianil, kasugamycin, kresoxim-methyl, mancozeb ( mancozeb), mandipropamid, maneb,

manzeb, mepanipyrim, mepronil, metalaxyl, metam-ammonium, metam-sodium, metconazole, methasulfocarb, bromide methyl bromide, methylisothiocyanate, metominostrobin, metrafenone, mildiomycin, myclobutanil, nickel dimethyldithiocarbamate, nuarimol , orysastrobin, oxadixyl, oxathiapiprolin, oxine-copper, oxolinic acid, oxpoconazole fumarate, oxycarboxin ( oxycarboxin, oxytetracycline, pebulate, pefurazoate, penconazole, pencycuron, penflufen, penthiopyrad, picarbutrazox, picoxist picoxystrobin, piperalin, polycarbamate, polyoxin-B, polyoxins, potassium hydrogen carbonate,

probenazole, prochloraz, procymidone, propamocarb, propiconazole, propineb, proquinazid, prothioconazole, pyraclostrobin , pyrametostrobin, pyraoxystrobin, pyrazophos, pyribencarb, pyridinitril, pyrifenox, pyrimethanil, pyriofenone, pyroquilon , quinoxyfen, quintozene, sedaxane, silver, simeconazole, sodium hydrogen carbonate, sodium hypochlorite, spiroxamine, streptomycin, sulfur, tebfloquin, tebuconazole, tecloftalam, terbinafine, tetraconazole, thiabendazole, thiadiazin, thifluzamide ), thiophanate,

thiophanate-methyl, thiram, tiadinil, tolclofos-methyl, tolprocarb, tolylfluanid, triadimefon, triadimenol, triclofos-methyl piricarb, tricyclazole, tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole, uniconazole-P ), validamycin (-A), vinclozolin, zarilamid, zinc sulfate, zineb, ziram, and zoxamide.

Examples of compounds having herbicidal activity include
acronifen, acifluofen-sodium, alachlor, alloxydim, amicarbazone, amidosulfuron, anilofos, aslam, atrazine ( atrazine), azimsulfuron, benfuresate, bensulfuron-methyl, bentazone, benthiocarb, benzobicyclon, benzofenap, bialaphos ), bifenox, bromobutide, bromoxynil, butamifos, cafenstrole, calcium peroxide, carbetamide, cinosulfuron, clomeprop, cyclosulfamuron, cyhalofop-butyl, daimuron, desmedipham, diclofop-methyl, diflufenican,

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

mefenacet, mesosulfuron, metamitron, methabenzthiazuron, metosulam, metribuzin, napropamide, neburon, oxadiargyl, oxadiazon oxadiazon, oxaziclomefone, paraquat, pendimethalin, pentoxazone, phenmedipham, pretilachlor, propoxycarbazone, prosulfocarb ), pyraclonil, pyraflufen n-ethyl, pyrazolate, pyrazosulfuro n-ethyl, pyributicarb, pyriftalid, pyriminobac-methyl , quizalofop-ethyl, sethoxydim, simazine, sulcotrione, sulfentrazone, thenylchlor, triaziflam, tribufos, etc. can be exemplified.

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

It can also be used by mixing with prohydrojasmon, thidiazuron, trinexapac, uniconazole-P, wax, and the like.
Repellents such as capsaicin, carane-3,4-diol, citronellal, deet, dimethyl phthalate, hinokitiol, limonene , linalool, menthol, menthone, naphthalene, thiram, etc.;
Synergists such as methylenedioxynaphthalene, naphthyl propynyl ether, nitrobenzyl thiocyanate, octachlorodipropyl ether, pentynyl phthalimide, phenyl sarioxon, piperonyl 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), entomopox virus (EPV), granulosis virus (GV), nuclear polyhedrosis virus ( Virus preparations such as nuclear polyhedrosis virus (NPV), Beauveria bassiana, Beauveria brongniartii, Monacrosporium phymatophagum, Paecilomyces fumosoroseus, Pasteuria penetrans ), Steinernema carpocapsae, Steinernema glaseri, Steinernema kushidai, Verticillium lecanii, etc. microbial pesticides, Agrobacterium radiobacter, Bacillus subtilis, non-pathogenic Erwinia carotovora, non-pathogenic Fusarium oxysporum, Pseudomonas CAB-02 ( Pseudomonas CAB-02), Pseudomonas fluorescens, Talaromyces flavus, Trichoderma atroviride, Trichoderma lignorum, microbial pesticides used as fungicides, Xanthomonas・Similar effects can be expected by mixing with biopesticides such as Xanthomonas campestris, which are used as herbicides.

Furthermore, as biological pesticides, for example, Amblyseius californicus, Amblyseius cucumeris, Amblyseius degenerans, Aphidius colemani, Aphidoletes aphidimyza, Yamato lacewing Chrysoperia carnea, Dacnusa sibirica, Diglyphus isaea, Encarsia formosa, Eretmocerus eremicus, Franklinothrips vespiformis, Harmonia axyridis ; Piocoris varius), natural enemy organisms such as codrelure, cuelure, geraniol, gyptol, liblure, looplure, methyl eugenol, orfralure , peachflure, phycilure, pyrimalure, turpentine, and the like.
Example

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

Example 1. Synthesis of 2,4-dimethyl-1-(1,1,1-trifluoroethyl)thiobenzene A solution of 2,4-dimethylbenzenethiol (14.7 mL) in DMF (200 mL) was cooled in an ice bath. Then, potassium carbonate (18.3 g) and Rongalite (5.17 g) were added. To this, 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 then stirred for 22 hours while the temperature of the reaction mixture was raised to room temperature. The reaction solution was poured into ice water and extracted with hexane three times. The combined organic layer was washed with saturated brine and dried over sodium sulfate. By distilling off the solvent under reduced pressure, 23.2 g of 2,4-dimethyl-1-(1,1,1-trifluoroethyl)thiobenzene was obtained.

Example 2. Synthesis of 2,4-dimethyl-5-[(1,1,1-trifluoroethyl)thio]benzaldehyde 2,4-Dimethyl-1-(1,1 ,1-trifluoroethyl)thiobenzene (10.0 g) was added, and the inside of the container was purged with argon. 100 mL of dry dichloromethane was added thereto and cooled in an ice bath. To this, 100 mL of titanium tetrachloride (1.0 M dichloromethane solution) was added dropwise over 3 hours. After stirring for 13 minutes in an ice bath, dichloromethyl methyl ether (4.46 mL) was slowly added, and the mixture was stirred for 2.5 hours while warming to room temperature, and further stirred for 16 hours at room temperature. After that, the reaction solution was poured into a saturated aqueous solution of ammonium chloride, and the organic layer was separated. The aqueous layer was extracted twice with hexane, and the combined organic layers were washed twice with 0.1N hydrochloric acid and once with saturated brine. After drying with sodium sulfate, 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) and 2,4-dimethyl-5-[(1,1,1-trifluoroethyl)thio]benzaldehyde (7.82 g) was added. Obtained.

Example 3. 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% aqueous hydrogen peroxide (0.420 mL) and sodium tungstate dihydrate were added, and the mixture was stirred at room temperature for 16 hours. After that, water was added, the precipitated solid was separated by filtration, washed with water and dried to obtain 0.860 g of a white solid of 2,4-dimethyl-5-[(1,1,1-trifluoroethyl)sulfinyl]benzaldehyde. Obtained.

Example 4. Synthesis of 1-(2,4-dimethyl-5-((2,2,2-trifluoroethyl)sulfinyl)benzyl)-4-(trifluoromethyl)piperidine 2,4-dimethyl-5- Dissolve [(1,1,1-trifluoroethyl)sulfinyl]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. Sodium triacetoxyborohydride (389 mg) was added thereto, and the mixture was stirred at room temperature for 3 hours. Ethyl acetate, water, and saturated aqueous sodium hydrogencarbonate solution were added to stop the reaction. The organic layer was separated and the aqueous layer was extracted twice with ethyl acetate. The combined organic layer was dried with saturated saline and sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was sprinkled over silica gel and purified by silica gel column chromatography (n-hexane:EtOAc=2:1/Rf=0.5) to give 1-(2,4-dimethyl-5-((2,2,2- 416 mg of trifluoroethyl)sulfinyl)benzyl)-4-(trifluoromethyl)piperidine were 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-trifluoroethyl) Sodium tetrahydroborate (174 mg) was added to a solution of fluoroethyl)thio)benzaldehyde (957 mg) in ethanol (13 mL) at room temperature, and the mixture was stirred for 30 minutes. The combined organic layers were washed with saturated brine, dried over sodium sulfate, the solvent was distilled off under reduced pressure, and the resulting residue was subjected to silica gel column chromatography (n-hexane:EtOAc=4:1). /Rf=0.5) to obtain 895 mg of (2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)methanol.

Example 6. Synthesis of 2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)benzyl methanesulfonate (2-fluoro-4-methyl-5-((2,2, 2-Trifluoroethyl)thio)phenyl)methanol (2.85 g) was dissolved in 40 mL of dichloromethane and cooled in an ice bath. Methanesulfonyl chloride (2.60 mL) was added thereto, and a solution of triethylamine (1.90 mL) in 7 mL of dichloromethane was added dropwise over 25 minutes. After stirring for 80 minutes while warming to room temperature, water was added. The organic layer was separated and the aqueous layer was extracted once with ethyl acetate. The combined organic layer was washed with saturated brine, dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:EtOAc=4:1/Rf=0.3) and treated with 2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio ) 3.20 g of a colorless oil of benzyl methanesulfonate were obtained.

Example 7. Synthesis of 2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)benzyl methanesulfonate 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, saturated aqueous sodium hydrogen carbonate solution was added and stirred. After separating the organic layer, the aqueous layer was extracted twice with chloroform. The combined organic layer was washed with saturated brine and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (n-hexane:EtOAc=1:1/Rf=0.5) to give 2-fluoro-4-methyl-5-((2,2, 180 mg of a white solid of 2-trifluoroethyl)sulfinyl)benzyl methanesulfonate were obtained.

Example 8. Synthesis of 1-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)benzyl)-4-methylpiperidine 2-fluoro-4-methyl-5- Dissolve ((2,2,2-trifluoroethyl)sulfinyl)benzyl methanesulfonate (147 mg) in 5 mL of DMF, add 4-methylpiperidine (0.052 mL) and potassium carbonate (71.4 mg), and add 5 mL of DMF. 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 layer was washed with saturated brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (n-hexane:EtOAc=1:1/Rf=0.5), and 1-(2-fluoro-4-methyl-5-(( 112 mg of 2,2,2-trifluoroethyl)sulfinyl)benzyl)-4-methylpiperidine was obtained.

Table 7 below shows the ¹ H-NMR data of the compounds produced in the same manner as in the above examples.
Table 7

The formulations containing the compound of the present invention will be specifically described below by giving some examples of formulations, but the compounds of the present invention, auxiliary ingredients, and the amount of addition thereof are, of course, limited only to the following formulation examples. is not. In addition, all the parts in the formulation examples represent parts by mass.

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

Formulation Example 2 EW-1
The compound of the present invention (20 parts) and Nucalgen D-230 (polyoxyethylene castor oil, Takemoto Oil Co., Ltd.) (15 parts) are mixed and homogenized, and then water (59.8 parts) is added while stirring. was slowly added to obtain a dispersion. This dispersion was dispersed in propylene glycol (reagent) (5.0 parts), and KELZAN (xanthan gum, Sansho Co., Ltd.) (0.2 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 Rheodol 430V (polyoxyethylene sorbitol tetraoleate, Kao Corporation) (24 parts) to obtain a dispersion. This dispersion and water (50.8 parts) were dispersed using a homogenizer, and KELZAN (xanthan gum, Sansho Co., Ltd.) (0.2 parts) dispersed in propylene glycol (reagent) (5.0 parts) was added to obtain an emulsion formulation.

Formulation Example 4 Microemulsion Compound of the present invention (10 parts), xylene (reagent) (20 parts), Nucalgen D-230 (polyoxyethylene castor oil, Takemoto Oil Co., Ltd.) (20 parts), Airol 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 Aqueous solvent A compound of the present invention (5 parts), Lunox P-65L (sodium alkylbenzenesulfonate, Toho Chemical Industry Co., Ltd.) (3 parts) and sodium hydrogen carbonate (reagent) (82 parts) were uniformly mixed. After that, it was pulverized using a fine pulverizer to obtain a water solvent.

Formulation Example 6 Solution-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 Co., Ltd.) (10 parts) are uniformly mixed and dissolved. to obtain a liquid formulation.

Formulation Example 7 Solution-2
Compound of the present invention (0.5 parts), N-methyl-2-pyrrolidone (reagent) (30 parts), Nucalgen D-230 (polyoxyethylene castor oil, Takemoto Oil Co., Ltd.) (10 parts) and water (59 parts) .5 parts) were uniformly mixed and dissolved to obtain a liquid formulation.

Formulation Example 8 Wettable powder Compound of the present invention (20 parts), Toxil GU-N (white carbon, Oriental Silicas Corporation) (20 parts), Sorpol 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 pulverized using a fine pulverizer to obtain a wettable powder.

Formulation Example 9 Water-dispersible granules Compound of the present invention (50 parts), Sanex P252 (sodium ligninsulfonate, Nippon Paper Industries Co., Ltd.) (5 parts), and SS clay (clay, Showa KDE Co., Ltd.) (45 parts) After mixing, it was pulverized using a fine pulverizer to obtain a pulverized material. Water was added to the pulverized product, and the mixture was kneaded well, extruded and granulated, dried and granulated to obtain water dispersible granules.

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

Formulation Example 11 Granules-1
Compound of the present invention (5 parts), Airol CT-1L (sodium dioctyl sulfosuccinate, Toho Chemical Industry Co., Ltd.) (2 parts), bentonite Sado (bentonite, Kunimine Industry Co., Ltd.) (30 parts), and NK-300 ( Clay (Showa KDE Co., Ltd.) (63 parts) was uniformly mixed, water was added and well kneaded, followed by extrusion granulation, drying and sizing to obtain granules.

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

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

Formulation Example 14 Microgranules-2
The compound of the present invention (5 parts) and Tokusil GU-N (5 parts) were mixed, pulverized using a fine pulverizer, and uniformly mixed with Iide silica sand (silica sand, JFE Mineral Co., Ltd.) (80 parts). This mixture was further mixed while spraying an aqueous solution obtained by diluting Toxanon GR-31A (polycarboxylic acid type surfactant, Sanyo Chemical Industries, Ltd.) (10 parts) to obtain a granular composition. This granular composition was dried to obtain fine granules.

Formulation Example 15 Dust agent The compound of the present invention (5 parts), Tokusil GU-N (5 parts) and Omori fine powder clay (clay, Taisei Sangyo Co., Ltd.) (90 parts) were uniformly mixed, and then a fine pulverizer was used. and pulverized to obtain a powder.

比較剤Ａ （US 2009/0082389 A1記載の13-24） Next, the effects and usefulness of the compounds of the present invention will be described with reference to specific examples. The compounds used for comparison are indicated by the following compound symbols.

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

Test Example 1: Adulticidal test against two-spotted spider mite (Tetranychus urticae Koch) A 430 ml polyethylene cup filled with water was covered with a lid with a hole (approximately 5 mm in diameter) in the center. A circular filter paper with a diameter of 6.5 cm was cut with a width of about 5 mm, and the strip-shaped part hanging downward was inserted through the hole in the lid so as to be immersed in the water in the cup, and absorbent cotton was placed on the filter paper. In this way, two leaf discs (2 cm x 5 cm) made from primary leaves of kidney beans were placed on the absorbent cotton in which the water in the cup was constantly replenished. inoculated. This cup was placed in an acrylic cylinder with a height of 50 cm and a diameter of 10 cm, and a water-diluted solution (500 ppm) of the emulsion prepared according to Formulation Example 1 was sprayed in an amount of 2.0 ml per cup using an air brush. After spraying, it was kept in a constant temperature room at 25°C. Four days after the treatment, the survival and writhing of the adults were examined under the binocular, and the killing rate (%) was determined by regarding writhing worms as dead. The test was carried out using 1 cup for each section.

Insecticide 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 and D-4 showed 100% insecticidal rate. On the other hand, Comparative Agent A had an insecticidal rate of 0%.

Test Example 2: Density suppression test against two-spotted spider mite (Tetranychus urticae Koch) A 430 ml polyethylene cup filled with water was covered with a lid having a hole (approximately 5 mm in diameter) in the center. A circular filter paper with a diameter of 6.5 cm was cut with a width of about 5 mm, and the strip-shaped part hanging downward was inserted through the hole in the lid so as to be immersed in the water in the cup, and absorbent cotton was placed on the filter paper. In this way, two leaf discs (2 cm x 5 cm) made from primary leaves of kidney beans were placed on the absorbent cotton in which the water in the cup was constantly replenished. inoculated. This cup was placed in an acrylic cylinder with a height of 50 cm and a diameter of 10 cm, and a water-diluted solution (500 ppm) of the emulsion prepared according to Formulation Example 1 was sprayed in an amount of 2.0 ml per cup using an air brush. After spraying, it was kept in a constant temperature room at 25°C. 7 days after treatment, the next generation density suppression effect on eggs laid by adults is 100 (density suppression rate: 100%), 95 (same: 99-95%), 80 (same: 94-80%), 50 (same: 79-50%) and 0 (same: less than 50%), and based on the results, the next-generation density suppression rate was calculated using the following formula. The test was carried out using 1 cup for 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 and D-4 showed a density suppression rate of 100%. On the other hand, the comparative agent A had a density suppression rate of 0%.

Test Example 3: Adulticidal test against orange spider mite (Panonychus citri McGregor) A 430 ml polyethylene cup filled with water was covered with a hole (approximately 5 mm in diameter) in the center. A circular filter paper with a diameter of 6.5 cm was cut with a width of about 5 mm, and the strip-shaped part hanging downward was inserted through the hole in the lid so as to be immersed in the water in the cup, and absorbent cotton was placed on the filter paper. In this way, two leaf discs (2 cm x 5 cm) made from fully expanded citrus leaves were placed on the absorbent cotton in which the water in the cup was constantly replenished. was inoculated. This cup was placed in an acrylic cylinder with a height of 50 cm and a diameter of 10 cm, and a water-diluted solution (500 ppm) of the emulsion prepared according to Formulation Example 1 was sprayed in an amount of 2.0 ml per cup using an air brush. After spraying, it was kept in a constant temperature room at 25°C. Four days after the treatment, the adult worms were examined under the binocular for life, death and writhing. The test was carried out using 1 cup for each section.

Insecticide 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, and D-3 exhibited an insecticidal rate of 100%. Comparative agent A, on the other hand, had an insecticidal rate of 0%.

Test Example 4 Density Suppression Test Against Citrus Spider Mite (Panonychus citri McGregor) A 430 ml polyethylene cup filled with water was covered with a lid having a hole (approximately 5 mm in diameter) in the center. A circular filter paper with a diameter of 6.5 cm was cut with a width of about 5 mm, and the strip-shaped part hanging downward was inserted through the hole in the lid so as to be immersed in the water in the cup, and absorbent cotton was placed on the filter paper. In this way, two leaf discs (2 cm x 5 cm) made from fully expanded citrus leaves were placed on the absorbent cotton in which the water in the cup was constantly replenished. was inoculated. This cup was placed in an acrylic cylinder with a height of 50 cm and a diameter of 10 cm, and a water-diluted solution (500 ppm) of the emulsion prepared according to Formulation Example 1 was sprayed in an amount of 2.0 ml per cup using an air brush. After spraying, it was kept in a constant temperature room at 25°C. 7 days after treatment, the next generation density suppression effect on eggs laid by adults is 100 (density suppression rate: 100%), 95 (same: 99-95%), 80 (same: 94-80%), 50 (same: 79-50%) and 0 (same: less than 50%), and based on the results, the next-generation density suppression rate was calculated using the following formula. The test was carried out using 1 cup for 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 and D-4 exhibited a density suppression rate of 100%. On the other hand, the comparative agent A had a density suppression rate of 0%.

Test Example 5: Effect test on Meloidogyne incognita (Kofoid et White) Chitwood 200 ml of test soil adjusted to a nematode density of 200 / soil 20 g Put in a styrene cup (diameter 9 cm, height 6.5 cm). After irrigating 50 ml of a water-diluted emulsion (100 ppm) of the emulsion prepared according to Formulation Example 1, tomatoes were seeded (13 grains/pot). After sowing, it was grown in a greenhouse. On the 14th day after seeding, each strain was examined for the degree of nodule formation in 5 stages based on the following evaluation criteria, and the nekobu index and control value were calculated based on the following formula. The test was carried out using one pot for each group.
Degree of nodule (evaluation criteria): 0 (no nodule), 1 (1-2 nodule), 2 (3 or more nodule), 3 (large or connected nodule) less than 50% of total roots), 4 (more than 50% of total roots have galls)

Root-knot index = Σ (degree of root-knot x number of relevant strains) / (4 x number of surveyed strains)

Control value (%) = [1-(root-cob index in treated area/root-cob index in untreated area)] x 100

As a result, the compounds of the present invention of compound numbers 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 gave a control value of 0%.

Claims (19)

the following formula (1),

[In the formula,
R ¹ is a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _2-6 alkenyl group, a C _2-6 haloalkenyl group, a C _2-6 alkynyl group, a C _2-6 haloalkynyl group, and a C _{3 -6} cycloalkyl C _1-6 alkyl group or C _3-6 halocycloalkyl C _1-6 alkyl group,
n is an integer from 0 to 2,
X is a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _3-6 cycloalkyl group, a C _2-6 alkenyl group, a C _2-6 alkynyl group, a C _2-6 haloalkenyl group, a C _{2- 6} haloalkynyl group, _C1-6 alkoxy group, _C1-6 haloalkoxy group, C3-6 _{halocycloalkyl} group, _C1-6 alkoxycarbonyl group, _C1-6 alkoxymethyl group, formyl group, halogen atom , represents a cyano group or a 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 and represent a hydrogen atom, a halogen atom, a C _1-6 alkyl group or a C _1-6 haloalkyl group,
J ¹ represents a direct connection, -CR ^3a R ^3b - or -CR ^3a R ^3b -CR ^3c R ^3d -,
J ² represents a direct connection or -CR ^3e R ^3f -,
R ^3a , R ^3b , R ^3c , R ^3d , R ^3e and R ^3f may be the same or different and represent a hydrogen atom, a halogen atom, a C _1-6 alkyl group or a C _1-6 haloalkyl group,
M represents ^-CR4aR4b- , ^-NR5- , -O-, -S-, -S ⁽ O)- or -S(O) _2- ,
R ^4a and R ^4b , which may be the same or different, each represents 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 It represents a C _1-6 haloalkylsulfonyl group. ]
1-benzylamine derivative represented by, its N-oxide or its salt. the following formula (2),

[In the formula,
R ¹ is a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _2-6 alkenyl group, a C _2-6 haloalkenyl group, a C _2-6 alkynyl group, a C _2-6 haloalkynyl group, and a C _{3 -6} cycloalkyl C _1-6 alkyl group or C _3-6 halocycloalkyl C _1-6 alkyl group,
n is an integer from 0 to 2,
X is a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _3-6 cycloalkyl group, a C _2-6 alkenyl group, a C _2-6 alkynyl group, a C _2-6 haloalkenyl group, a C _{2- 6} haloalkynyl group, _C1-6 alkoxy group, _C1-6 haloalkoxy group, C3-6 _{halocycloalkyl} group, _C1-6 alkoxycarbonyl group, _C1-6 alkoxymethyl group, formyl group, halogen atom , represents a cyano group or a 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 R ⁸ groups, C _1-3 alkylphenyl group (wherein the phenyl group is , ^optionally substituted with one or more R9) or a ^C3-6 cycloalkyl group _optionally substituted with one or more R10,
R ⁸ represents a halogen atom, a C _1-6 alkyl group or a C _1-6 haloalkyl group,
R ⁹ represents a halogen atom, a C _1-6 alkyl group or a 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, its N-oxide or its salt. The 1-benzylamine derivative, its N-oxide or its salt according to claims 1 or 2, wherein R ¹ represents a C _1-6 alkyl group or a C _1-6 haloalkyl group. 3. The 1-benzylamine derivative, its N-oxide or its salt according to claim 1 or 2, 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, its N-oxide or its salt according to any one of claims 1 to 4, wherein n represents 1. the following formula (3),

[In the formula,
R ¹ is a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _2-6 alkenyl group, a C _2-6 haloalkenyl group, a C _2-6 alkynyl group, a C _2-6 haloalkynyl group, and a C _{3 -6} cycloalkyl C _1-6 alkyl group or C _3-6 halocycloalkyl C _1-6 alkyl group,
n is an integer from 0 to 2,
X is a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _3-6 cycloalkyl group, a C _2-6 alkenyl group, a C _2-6 alkynyl group, a C _2-6 haloalkenyl group, a C _{2- 6} haloalkynyl group, _C1-6 alkoxy group, _C1-6 haloalkoxy group, C3-6 _{halocycloalkyl} group, _C1-6 alkoxycarbonyl group, _C1-6 alkoxymethyl group, formyl group, halogen atom , represents a cyano group or a nitro group,
Y represents a hydrogen atom, a halogen atom, a _C1-6 alkyl group or a _C1-6 haloalkyl group. ]
1-benzyl alcohol derivative represented by. the following formula (1),

wherein X, Y, n, ^R1 , ^R2a , ^{R2b, R2c, R2d , M} , J1 and J2 ^are as defined in claim ¹ ; ]
A method for producing a 1-benzylamine derivative represented by
The following formula (4),

[wherein X, Y, n and R ¹ are as defined in claim 1; ]
A benzaldehyde derivative represented by
Formula (5),

[wherein 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 amines represented by or salts thereof. the following formula (2),

[Wherein, 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
The following formula (4),

[wherein X, Y, n and R ¹ are as defined in claim 2; ]
A benzaldehyde derivative represented by
the following formula (6),

[wherein R ⁶ and R ⁷ are as defined in claim 2; ]
A production method comprising reacting with amines represented by or salts thereof. the following formula (3),

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

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

wherein X, Y, n, ^R1 , ^R2a , ^{R2b, R2c, R2d , M} , J1 and J2 ^are as defined in claim ¹ ; ]
A method for producing a 1-benzylamine derivative represented by
the following formula (7),

[In the formula,
R ¹ is a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _2-6 alkenyl group, a C _2-6 haloalkenyl group, a C _2-6 alkynyl group, a C _2-6 haloalkynyl group, and a C _{3 -6} cycloalkyl C _1-6 alkyl group or C _3-6 halocycloalkyl C _1-6 alkyl group,
n is an integer from 0 to 2,
X is a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _3-6 cycloalkyl group, a C _2-6 alkenyl group, a C _2-6 alkynyl group, a C _2-6 haloalkenyl group, a C _{2- 6} haloalkynyl group, _C1-6 alkoxy group, _C1-6 haloalkoxy group, C3-6 _{halocycloalkyl} group, _C1-6 alkoxycarbonyl group, _C1-6 alkoxymethyl group, formyl group, halogen atom , represents a cyano group or a 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. ]
A compound represented by
the following formula (5),

[wherein 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 amines represented by or salts thereof. the following formula (2),

[wherein X, Y, n, ^R1 , R6 and ^R7 are as defined in claim ² ; ]
A method for producing a 1-benzylamine derivative represented by
the following formula (7),

wherein R ¹ , n, X, Y and Z are as defined in claim 10; ]
A compound represented by
the following formula (6),

[wherein R ⁶ and R ⁷ are as defined in claim 2; ]
A production method comprising reacting with amines represented by or salts thereof. An agricultural and horticultural agent containing the 1-benzylamine derivative, its N-oxide or its salt according to any one of claims 1 to 5. An agricultural and horticultural acaricide containing the 1-benzylamine derivative, its N-oxide or its salt according to any one of claims 1 to 5. An agricultural and horticultural nematode control agent containing the 1-benzylamine derivative, N-oxide thereof or salt thereof according to any one of claims 1 to 5. An agricultural and horticultural pest control agent containing the 1-benzylamine derivative, its N-oxide or its salt according to any one of claims 1 to 5. An agricultural and horticultural disease preventive agent containing the 1-benzylamine derivative, its N-oxide or its salt according to any one of claims 1 to 5. 13. A method of controlling plant pests, comprising the step of treating pests and/or their habitat and/or seeds and/or plant propagation material with an agrohorticultural agent according to claim 12. A method for controlling plant pests, comprising the step of treating a place where useful crops are to be grown, a place where useful crops are grown, or growing crops, with the agricultural and horticultural agent according to claim 12. . A method for preparing an agricultural chemical composition, comprising the step of mixing the agricultural and horticultural agent according to claim 12 with an extender and/or a surfactant.