WO2022004673A1

WO2022004673A1 - Novel hydrazone derivative and agricultural and horticultural agent containing same as active ingredient

Info

Publication number: WO2022004673A1
Application number: PCT/JP2021/024404
Authority: WO
Inventors: 秀一薄井; 恒一荒木; 一秋小山; 祥森下; 俊樹福地
Original assignee: アグロカネショウ株式会社
Priority date: 2020-06-29
Filing date: 2021-06-28
Publication date: 2022-01-06
Also published as: JP2023113975A

Abstract

Provided are: a compound having excellent effect against various pests, and an intermediate of the compound; an agricultural and horticultural agent utilizing the compound; a method for producing the compound or the intermediate; and a method for using said compound. Contained as an active ingredient is a compound represented by formula (1). In the formula: R₁ represents, for example, a hydrogen atom and a C_1-6 alkyl group; R₂ represents a formyl group; R₃ represents, for example, a C_1-6 alkyl group; R₄ represents, for example, a hydrogen atom and a C_1-6 alkyl group; R₅ represents a C_1-6 haloalkyl group; X represents, for example, a hydrogen atom and a C_1-6 alkyl group; and n represents an integer between 1 and 5.

Description

New hydrazone derivative and agricultural and horticultural chemicals containing it as an active ingredient

The present invention relates to a novel hydrazone derivative and an agricultural and horticultural agent containing the compound as an active ingredient, particularly an agricultural and horticultural pest control agent or a nematode control agent, and a method of using the same.

In the field of agriculture and horticulture, plant pest control agents for controlling various pests have been developed and put into practical use. However, the emergence of pests or diseases that have acquired drug resistance has become a problem, and the development of new drugs is eagerly desired.
Patent Document 1 describes that a semicarbazone derivative is useful as an agricultural insecticide. However, the compound of Patent Document 1 does not disclose a hydrazone compound having a pyrazolyl ring between a phenyl group and a sulfonylamide group and further having a haloalkylsulfonamide as in the present invention. Furthermore, the compound described in Patent Document 1 does not describe any effect on nematodes.
Further, the following compounds are disclosed as related compounds of the compound of the present invention (for example, Patent Documents 2 to 5). However, the compounds described in Patent Documents 2 and 3 do not have a sulfonamide group bonded to a hydrazone group via a methylene group, and the compounds of Patent Documents 4 and 5 are different from the compounds of the present invention. It forms a ring structure containing a carbon atom of a hydrazone group and a methylene group adjacent thereto, and has a significantly different basic skeleton, and both of them disclose compounds having a significantly different chemical structure from the compound of the present invention. It's just that.

U.S. Pat. No. 5798311 Japanese Unexamined Patent Publication No. 63-93761 Japanese Unexamined Patent Publication No. 8-073436 International Publication No. 01/36381 Japanese Patent Application Laid-Open No. 2002-155044

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

As a result of diligent research to solve the above problems, the present inventors have found that the hydrazone derivative represented by the following formula (1), which is a novel compound not described in the literature, is an agricultural and horticultural drug, particularly an agricultural and horticultural pest. The present invention has been completed by finding it useful as a control agent or a nematode control agent.
That is, the present invention has the following equation (1).

[During the ceremony,
R ₁ is a hydrogen atom, C _1-6 alkyl group, C _1-6 alkenyl group, C _1-6 alkynyl group, C _1-6 haloalkyl group, C _1-6 alkoxy C _1-6 alkyl group, C _{1- 6} alkoxycarbonyl C _1-6 alkyl group, cyano C _1-6 alkyl group or optionally substituted benzyl group, indicating
R ₂ indicates a formyl group, or R ₁ and R ₂ together,

May form,
R ₃ indicates a C _1-6 alkyl group,
R ₄ is a hydrogen atom, C _1-6 alkyl group, C _1-6 haloalkyl group, C _3-6 cycloalkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _2-6 haloalkyl group. , C _2-6 haloalkynyl group, C _1-6 alkoxy C _1-6 alkyl group, C _1-6 alkoxycarbonyl C _1-6 alkyl group or optionally substituted benzyl group.
R ₅ represents a C _1-6 haloalkyl group
R ₆ indicates OR ₇ or NR ₈ R ₉
R ₇ 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 hydroxy C. _1-6 alkyl group, C _1-6 alkoxy C _1-6 alkyl group, C _3-6 cycloalkyl group, C _3-6 cycloalkyl C _1-6 alkyl group or optionally substituted benzyl group.
R ₈ represents a hydrogen atom or a C _1-6 alkyl group.
R ₉ is a hydrogen atom, C _1-6 alkyl group, C _1-6 alkoxy group, C _1-6 haloalkyl group, C _2-6 alkenyl group, C _2-6 haloalkenyl group, C _2-6 alkynyl group, C _2-6 haloalkynyl group, hydroxy C _1-6 alkyl group, C _1-6 alkoxy C _1-6 alkyl group, C _3-6 cycloalkyl group, C _3-6 cycloalkyl C _1-6 alkyl group or substituted Indicates a benzyl group which may be, or R ₈ and R ₉ are attached to each other _{and together with the nitrogen atom to which R 6} and R ₇ are attached, 4 to 7 saturated or unsaturated. It may form a member ring,
X may be the same or different, hydrogen atom, C _1-6 alkyl group, C _1-6 haloalkyl group, C _3-6 cycloalkyl group, C _2-6 alkoxy group, C _2-6 alkynyl group, C. _2-6 haloalkoxy group, C _2-6 haloalkynyl group, C _1-6 alkoxy group, C _1-6 haloalkoxy group, C _1-6 alkylthio group, C _3-6 halocycloalkyl group, C _1-6 If it represents an alkoxycarbonyl group, a formyl group, a halogen atom, a cyano group or a nitro group, or if two Xs are present in place of a hydrogen atom on two adjacent carbon atoms, the two above. X may be combined with the carbon atoms to which each is bonded to form a saturated or unsaturated 5- or 6-membered ring, and
n indicates an integer from 1 to 5. ]
Regarding the hydrazone derivative represented by (1) or a salt thereof, further relating to an agricultural and horticultural agent containing the compound as an active ingredient, particularly an agricultural and horticultural pest control agent or a nematode control agent, a method of using the same, and a method for producing the compound and the like. It is a thing.

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

In the present specification, the following functional groups mean the following contents.
The "halogen atom" refers to a chlorine atom, a bromine atom, an iodine atom or a fluorine atom.
The "C _1-6 alkyl group" is, for example, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, an s-butyl group, a t-butyl group, n. -A linear or branched alkyl group having 1 to 6 carbon atoms such as a pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, an n-hexyl group, and an isohexyl group is shown.
The “C _1-6 haloalkyl group” refers to a linear or branched chain alkyl group having 1 to 6 carbon atoms substituted with one or more halogen atoms which may be the same or different.
Examples of the C _1-6 haloalkyl group include a fluoromethyl group, a chloromethyl group, a difluoromethyl group, a trifluoromethyl group, a chlorodifluoromethyl group, a bromodifluoromethyl group, a dichlorofluoromethyl group, a 1-fluoroethyl group, and 2 -Fluoroethyl group, 2-chloroethyl group, 2-bromoethyl group, 2-iodoethyl group, 2,2,2-trifluoroethyl group, 2,2,2-trichloroethyl group, pentafluoroethyl group, 2,2- Difluoroethyl group, 1-fluoroisopropyl group, 3-fluoropropyl group, 3-chloropropyl group, 3-bromopropyl group, heptafluoropropyl group, heptafluoroisopropyl group, 4-fluorobutyl group, 4-chlorobutyl, nonafluoro Examples thereof include a linear or branched haloalkyl group having 1 to 6 carbon atoms substituted with 1 to 9 halogen atoms such as a butyl group.

The “C _3-6 cycloalkyl” refers to, for example, a cycloalkyl group having 3 to 6 cyclic carbon atoms such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

Examples of the C _2-6 alkenyl group include a vinyl group, an allyl group, an isopropenyl group, a 2-butenyl group, a 3-butenyl group, a 1-methyl-2-propenyl group, a 2-pentenyl group and a 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- A carbon atom having at least one double bond at any position such as a hexenyl group, a 4-hexenyl group, a 5-hexenyl group, a 1,1-dimethyl-2-butenyl group, a 1,1-dimethyl-3-butenyl group, etc. Examples thereof include a linear or branched alkenyl group having a number of 2 to 6.
Examples of the C _2-6 haloalkenyl group include 1-fluorovinyl group, 2-fluorovinyl group, 2,2-difluorovinyl group, 3-chloro-2-propenyl group and 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, Linear or linear or defined above with 2-6 carbon atoms substituted with 1-9 halogen atoms having at least one double bond at any position, such as a 6-fluoro-2-hexenyl group. Examples include branched chain alkenyl groups.

Examples of the C _2-6 alkynyl group include an ethynyl group, a 2-propynyl group, a 1-methyl-2-propynyl group, a 1,1-dimethyl-2-propynyl group, a 1-butynyl group and a 2-butynyl group, 3 -Butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 1-methyl-3-butynyl group, 1,1-dimethyl-2- 2 to 6 carbon atoms having at least one triple bond at any position such as a butynyl group, 1,1-dimethyl-3-butynyl group, 1-methyl-3-pentynyl group, 1-methyl-4-pentynyl group, etc. Examples thereof include linear or branched alkynyl groups.
The C _2-6 haloalkynyl group includes a fluoroethynyl group, a 4,4,4-trifluoro-2-butynyl group, a 5,5,5-trifluoro-3-pentynyl group, and a 1-methyl-3,3. Substituted with 1-9 halogen atoms having at least one triple bond at any position such as 3-trifluoro-2-butynyl group, 1-methyl-5,5,5-trifluoro-2-pentynyl group Examples thereof include the linear or branched alkynyl group defined above having 2 to 6 carbon atoms.

Examples of the C _1-6 alkoxy group include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, a cyclopropyloxy group, an n-butoxy group, a sec-butoxy group, a tert-butoxy group and an n-pentoxy group. , N-Hexyloxy group and the like, a linear or branched alkoxy group having 1 to 6 carbon atoms can be mentioned.
Examples of the C _1-6 haloalkoxy group include fluoromethoxy group, dichloromethoxy group, trichloromethoxy group, difluoromethoxy group, trifluoromethoxy group, chlorodifluoromethoxy group, bromodifluoromethoxy group, dichlorofluoromethoxy group, 1-. Fluoroethoxy group, 2-fluoroethoxy group, 2-chloroethoxy group, 2-bromoethoxy group, 2-iodoethoxy group, 2,2,2-trifluoroethoxy group, 2,2,2-trichloroethoxy group, penta Fluoroethoxy group, 1-fluoroisopropoxy group, 3-fluoropropoxy group, 3-chloropropoxy group, 3-bromopropoxy group, 4-fluorobutoxy group, 4-chlorobutoxy group, etc., preferably 1 to 9 groups. Examples thereof include the linear or branched alkoxy group defined above having 1 to 6 carbon atoms substituted with a halogen atom.
The benzyl group which may be substituted includes, for example, a halogen atom defined above, a C _1-6 alkyl group, a C _1-6 alkoxy group, a C _1-6 haloalkyl group, and a C _1-6 haloalkoxy group. Examples thereof include a benzyl group which may be substituted.

Examples of the C _3-6 halocycloalkyl group include 1-fluorocyclopropyl, 2-fluorocyclopropyl, 2,2-difluorocyclopropyl, 2,2,3,3-tetrafluorocyclopropyl and 1-chlorocyclo. Propyl, 2-chlorocyclopropyl, 2,2-dichlorocyclopropyl, 2,2,3,3-tetrachlorocyclopropyl, 2,2-dibromocyclopropyl, 1-fluorocyclobutyl, 2-fluorocyclobutyl, 3 -Fluorocyclobutyl, 3,3-difluorocyclobutyl, 3,3-dichlorocyclobutyl, 1-fluorocyclopentyl, 2-fluorocyclopentyl, 3-fluorocyclopentyl, 2,2-difluorocyclopentyl, 3,3-difluorocyclopentyl 2 , 2-Dichlorocyclopentyl, 1-fluorocyclohexyl group and the like, preferably cycloalkyl groups defined above having 3 to 6 carbon atoms substituted with 1 to 9 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, and examples thereof include groups consisting of _{a combination of the C 3-6} cycloalkyl group defined above and the C _{1-6 alkyl group defined above.}

Examples of the C _1-6 alkoxycarbonyl group include methoxycarbonyl, ethoxycarbonyl, n-propyloxycarbonyl, n-butyloxycarbonyl, n-pentyloxycarbonyl, n-hexyloxycarbonyl, i-propyloxycarbonyl group and the like. , A carbonyl group having a C _{1-6 alkoxy group as defined above.}
C _1-6 Alkoxy C _1-6 alkyl group, e.g., methoxymethyl group, ethoxymethyl group, methoxyethyl group, ethoxyethyl group, 3-such as methoxypropyl group, C _1-6 alkoxy as defined above _{Examples include the C 1-6} alkyl group defined above having a group.

C _1-6 alkoxycarbonyl The _1-6 alkyl group includes, for example, a methoxycarbonylmethyl group, an ethoxycarbonylmethyl group, an n-propyloxycarbonylmethyl group, a 2-methoxycarbonylethyl group and the like, as defined above. Examples thereof include the C _1-6 alkyl group _{defined above having a 1-6 alkoxycarbonyl group.}
The cyano C _1-6 alkyl group, for example, cyanomethyl group, such as 1-cyanoethyl group, and a C _1-6 alkyl group as defined above having a cyano group.
Hydroxy C _1-6 alkyl groups include, for example, hydroxy groups such as hydroxymethyl group, 2-hydroxyethyl group, 2-hydroxypropyl group, 3-hydroxypropyl group, 3-hydroxy-2,2-dimethylpropyl group and the like. _Included are the C 1-6 alkyl groups defined above having.

Examples of the C _1-6 alkylthio group include a methylthio group, an ethylthio group, an n-propylthio group, an isopropylthio group, a cyclopropylthio group, an n-butylthio group, an s-butylthio group, a t-butylthio group and an n-pentylthio group. , N-Hexylthio group and the like, which have 1 to 6 carbon atoms and are substituted with the _{C 1-6 alkyl group defined above.}

In the compounds described herein, R ₈ and R ₉ can bond to each other _{and together with the nitrogen atoms attached to R 8} and R ₉ to form a 4- to 7-membered ring, which is a ring. It may be saturated or unsaturated. For example, examples of the saturated ring include an azacyclobutane ring, a pyrrolidine ring, a piperidine ring, a morpholine ring, a thiomorpholine ring, a hexamethyleneimine ring and the like, and examples of the unsaturated ring include pyrazole, imidazole and 1,3,4-triazole. , 1,2,3-triazole, tetrazole and the like.

In the compounds described herein, if two Xs are present in place of hydrogen atoms on two adjacent carbon atoms of the phenyl ring, these Xs will bond to each other and each X will be. Together with the bonded carbon atom, it can form a saturated or unsaturated 5- or 6-membered ring. As such saturated or unsaturated 5- or 6-membered rings, for example, they are fused with a phenyl ring to form an indane ring, a tetrahydronaphthalene ring, a naphthalene ring, or the like, respectively. When a saturated or unsaturated 5- or 6-membered ring is formed, the two Xs present in place of the hydrogen atoms on the two adjacent carbon atoms of the phenyl ring are, for example, -CH ₂ CH ₂ CH. _2- , -CH ₂ CH ₂ CH ₂ CH _2- , -CH = CHCH = CH-, -N = CHCH = CH-, -OCHCHCH _2- are formed. Thus, the saturated or unsaturated 5- or 6-membered ring may be a carbocycle or a heterocycle.

Examples of the salt of the hydrazone derivative represented by the above formula (1) of the present invention include inorganic acid salts such as hydrochlorides, sulfates, nitrates and phosphates, acetates, fumarates, maleates and shu. Organic acid salts such as acid salts, methane sulfonates, benzene sulfonates, and p-toluene sulfonates can be exemplified.
The compounds described herein may contain one or more asymmetric centers in their structural formulas, and may contain two or more optical isomers and diastereomers. It also includes all optical isomers and mixtures containing them in arbitrary proportions. Further, in the compound described in the present specification, two or more kinds of geometric isomers derived from a carbon-carbon double bond or a carbon-nitrogen double bond may be present in the structural formula, but the present invention. Also includes all geometric isomers and mixtures containing them in arbitrary proportions.
For example, in the compounds described herein, in the structural formula, the wavy line may be any of two or more geometric isomers derived from a carbon-carbon double bond or a carbon-nitrogen double bond. Means to include.

In the hydrazone derivative represented by the above formula (1) of the present invention, R ₁ represents a hydrogen atom or a C _1-6 alkyl group, R ₂ represents a formyl group, and R ₃ represents a methyl group or an ethyl group. Alternatively, it is preferable to show an isopropyl group.

Hereinafter, representative production of a novel hydrazone derivative represented by the above formula (1) of the present invention, an intermediate thereof, a hydrazone derivative represented by the formula (2), and a ketone derivative represented by the formula (16). Although the method is shown, the method for producing the above compound is not limited to these in the present invention.
Reaction equation 1

[During the ceremony,
R ₃ indicates a C _1-6 alkyl group,
R ₄ is a hydrogen atom, C _1-6 alkyl group, C _1-6 alkenyl group, C _1-6 alkynyl group, C _1-6 haloalkyl group, C _1-6 alkoxy C _1-6 alkyl group, C _{1- 6} Alkoxycarbonyl C _1-6 Alkyl group or optionally substituted benzyl group, indicating
R ₅ represents a C _1-6 haloalkyl group
X may be the same or different, hydrogen atom, C _1-6 alkyl group, C _1-6 haloalkyl group, C _3-6 cycloalkyl group, C _2-6 alkoxy group, C _2-6 alkynyl group, C. _2-6 haloalkenyl group, C _2-6 haloalkynyl group, C _1-6 alkoxy group, C _1-6 haloalkoxy group, C _1-6 alkylthio group, C _3-6 halocycloalkyl group, C _1-6 2 above, when an alkoxycarbonyl group, a formyl group, a halogen atom, a cyano group or a nitro group is indicated, or two Xs are present in place of a hydrogen atom on two adjacent carbon atoms. The Xs may be combined with the carbon atoms to which they are bonded to form a saturated or unsaturated 5- or 6-membered ring.
n indicates an integer from 1 to 5, and
Hal represents a halogen atom. ]
In the method represented by the reaction formula 1, the ketone derivative represented by the formula (16) is an α-halogen ketone compound represented by the formula (14) and a sulfone amide compound represented by the formula (15). It can be produced by reacting in an inert solvent in the presence or absence of a base.

As the solvent used in the reaction between the compound of the formula (14) and the compound of the formula (15), a known solvent can be widely used as long as it is inert to the reaction.
Here, the compound represented by the formula (14) is known and is described in, for example, International Publication No. 2002/068395, International Publication No. 2012/131010, JP-A-2014-37370 and the like. It can be easily prepared by the method.
The compound represented by the formula (15) can be easily obtained by, for example, the method described in JP-A-2008-222659, US Pat. No. 4,69,364, and the like.
Examples of such a solvent include an aliphatic or alicyclic hydrocarbon solvent such as hexane, cyclohexane and heptane, an aromatic hydrocarbon solvent such as benzene, chlorobenzene, toluene and xylene, methylene chloride and 1,2-. Halogenated hydrocarbon solvents such as dichloroethane and chloroform, ether solvents such as diethyl ether, tetrahydrofuran and 1,4-dioxane, ester solvents such as methyl acetate and ethyl acetate, ketone solvents such as acetone and methyl ethyl ketone, N, Examples thereof include amide-based solvents such as N-dimethylformamide, nitrile-based solvents such as acetonitrile and propionitrile, and aprotonic polar solvents such as N-methylpyrrolidone and N, N'-dimethylimidazolinone. One of these solvents can be used alone, or two or more of these solvents can be mixed and used as required.
As the base used in the reaction between the compound of the formula (14) and the compound of the formula (15), known inorganic bases and organic bases can be used. Examples of the inorganic base include alkali metal carbonates such as sodium carbonate, potassium carbonate and sodium bicarbonate, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, and alkali metal hydrogens such as sodium hydride and potassium hydride. Examples include ghosts. Examples of the organic base include alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium tert-butoxide, and amines such as triethylamine and pyridine. These bases can be used alone or in admixture of two or more.
Such a base can be used in an amount usually 1 to 100 equivalents, preferably 1 to 2 equivalents, relative to the α-halogen ketone compound represented by the above formula (14).

The ratio of the α-halogen ketone compound represented by the formula (14) to the sulfonamide compound represented by the formula (15) is 1 to 1 for the compound (15) with respect to the compound (14). It is more preferable to use 2 mol.
The reaction can usually be carried out in the range from −78 ° C. to the boiling point temperature of the solvent used, and it is preferable to carry out the reaction at room temperature to 100 ° C.
The reaction time varies depending on the reaction temperature and the like and cannot be unconditionally stated, but the reaction is usually completed in about 0.5 to 24 hours.
The target compound obtained in each of the above reactions can be easily isolated from the reaction mixture by a commonly used isolation means, for example, an organic solvent extraction method, a chromatography method, a recrystallization method, a distillation method or the like. Further, it can be purified by ordinary purification means.

Reaction equation 2

[In the formula, R ₁ is a hydrogen atom, C _1-6 alkyl group, C _1-6 alkenyl group, C _1-6 alkynyl group, C _1-6 haloalkyl group, C _1-6 alkoxy C _1-6 alkyl group. , C _1-6 alkoxycarbonyl C _1-6 alkyl group or optionally substituted benzyl group, R ₃ , R ₄ , R ₅ , X and n are as defined in formula (16) above. .. ]
In the method represented by the reaction formula 2, the hydrazone derivative represented by the formula (7) is a ketone compound represented by the formula (16) and a hydrazine compound represented by the formula (17) in the presence of an acid. Alternatively, it can be produced by reacting in an inert solvent in the absence.

As the solvent used in the reaction between the ketone derivative of the formula (16) and the hydrazine compound of the formula (17), known solvents can be widely used as long as they are inert to the reaction. Examples of such a solvent include alcohols such as methanol, ethanol, n-propanol and iso-propanol, aliphatic or alicyclic hydrocarbon solvents such as hexane, cyclohexane and heptane, benzene, chlorobenzene, toluene and xylene. Aromatic hydrocarbon solvents such as methylene chloride, 1,2-dichloroethane, halogenated hydrocarbon solvents such as chloroform, ether solvents such as diethyl ether, tetrahydrofuran, 1,4-dioxane, methyl acetate, ethyl acetate and the like. Examples thereof include an ester solvent, an amide solvent such as N, N-dimethylformamide, and a solvent such as N-methylpyrrolidone, N, N'-dimethylimidazolinone, and acetonitrile. One of these solvents can be used alone, or two or more of these solvents can be mixed and used as required.
As the acid used in the reaction between the compound of the formula (16) and the compound of the formula (17), known inorganic acids and organic acids can be used. Examples of the inorganic acid include hydrogen chloride, hydrogen bromide, sulfuric acid, nitric acid and the like. Examples of the organic acid include acetic acid, propionic acid, citric acid, methanesulfonic acid, ethanesulfonic acid, p-toluenesulfonic acid and the like. These acids may be used alone or in admixture of two or more.
Such an acid can be used in an amount usually 0.001 to 2 equivalents, preferably 0.01 to 1 equivalent, relative to the ketone compound represented by the formula (16).

The ratio of the ketone derivative of the formula (16) to the hydrazine compound represented by the formula (17) can be appropriately selected from a wide range, but the latter is 1 to 1 to 1 mol of the former. It is preferable to use 10 mol or more, and more preferably 2.0 to 5.0 mol.
The reaction is preferably carried out at 0 ° C. to the boiling point temperature of the solvent used, and more preferably from room temperature to heated reflux.
The reaction time varies depending on the reaction temperature and the like and cannot be unconditionally stated, but the reaction is usually completed in about 0.1 to 24 hours.
After completion of the reaction, it may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary. It is also possible to use the target product in the next reaction step without isolating it from the reaction system.

Reaction equation 3

[In the formula, R ₁₀ represents a C _1-6 alkyl group, and R ₁ , R ₃ , R ₄ , R ₅ , X and n are as defined in the above formulas (16) and (7). ]
In the method represented by the reaction formula 3, the hydrazone derivative represented by the formula (2) is a hydrazone derivative represented by the formula (7) and a formic acid and / or a formic acid derivative represented by the formula (8). It can be produced by a formylation reaction with.

As the solvent used in the formylation reaction of the hydrazone compound represented by the formula (7), known solvents can be widely used as long as they are inert to the reaction. Examples of such a solvent include an aliphatic or alicyclic hydrocarbon solvent such as hexane, cyclohexane and heptane, an aromatic hydrocarbon solvent such as benzene, chlorobenzene, toluene and xylene, methylene chloride and 1,2-. Dichloroethane, halogenated hydrocarbon solvents such as chloroform, alcohol solvents such as methanol and ethanol, ester solvents such as methyl formate, ethyl formate, methyl acetate and ethyl acetate, ketone solvents such as acetone and methyl ethyl ketone, N, N Examples thereof include amide solvents such as dimethylformamide, nitrile solvents such as acetonitrile and propionitrile, and aprotonic polar solvents such as N-methylpyrrolidone and N, N'-dimethylimidazolinone. One of these solvents can be used alone, or two or more of these solvents can be mixed and used as required.
Examples of the formylation agent used in the formylation reaction of the hydrazone compound represented by the formula (7) include formic acid, methyl formate, ethyl formate and the like.
Such a formylation agent can be used in an amount usually 1 to 100 equivalents, preferably 1 to 10 equivalents, relative to the hydrazone derivative represented by the above formula (7).
The reaction can usually be carried out within the range of −78 ° C. to the boiling point temperature of the solvent used, and it is preferable to carry out the reaction at 0 ° C. to the boiling point temperature.
The reaction time varies depending on the reaction temperature and the like and cannot be unconditionally stated, but the reaction is usually completed in about 0.1 to 24 hours.
The target compound obtained in each of the above reactions can be easily isolated from the reaction mixture by a commonly used isolation means, for example, an organic solvent extraction method, a chromatography method, a recrystallization method, a distillation method, or the like. Further, it can be purified by ordinary purification means.

Reaction equation 4

[In the formula, R ₁ represents a hydrogen atom, R ₁₀ represents a C _1-6 alkyl group, and R ₃ , R ₄ , R ₅ , R ₆ , X and n are the above formulas (1) to (1). As defined in 2). ]
Specific embodiments of the reaction formula 4 include those represented by the reaction formulas 5 and 7 described below.

Reaction equation 5

[In the equation, R ₁ represents a hydrogen atom, R ₁₀ represents a C _1-6 alkyl group, and R ₃ , R ₄ , R ₅ , X and n are as defined above. ]
In the method represented by the reaction formula 5, the hydrazone derivative represented by the formula (12) can be produced by reacting the hydrazone derivative represented by the formula (7) with the orthoformate ester (18). ..

The solvent used in the reaction between the hydrazone compound represented by the formula (7) and the orthoformate ester represented by the formula (18) is widely known as long as it is inert to the reaction. Can be used. Examples of such a solvent include an aliphatic or alicyclic hydrocarbon solvent such as hexane, cyclohexane and heptane, an aromatic hydrocarbon solvent such as benzene, chlorobenzene, toluene and xylene, methylene chloride and 1,2-. Dichloroethane, halogenated hydrocarbon solvents such as chloroform, alcohol solvents such as methanol and ethanol, ester solvents such as methyl formate, ethyl formate, methyl acetate and ethyl acetate, ketone solvents such as acetone and methyl ethyl ketone, N, N Examples thereof include amide solvents such as dimethylformamide, nitrile solvents such as acetonitrile and propionitrile, and aprotonic polar solvents such as N-methylpyrrolidone and N, N'-dimethylimidazolinone. One of these solvents can be used alone, or two or more of these solvents can be mixed and used as required.
Examples of the orthoformate ester (18) used in the iminization reaction of the hydrazone compound represented by the formula (7) include methyl orthoformate, ethyl orthoformate, propyl orthoformate, butyl orthoformate and the like.
Such an orthoformate ester (18) can be used in an amount usually 1 to 20 equivalents, preferably 2 to 10 equivalents, relative to the hydrazone derivative represented by the above formula (7).
The reaction can usually be carried out within the range of −78 ° C. to the boiling point temperature of the solvent used, and it is preferable to carry out the reaction at 0 ° C. to the boiling point temperature.
The reaction time varies depending on the reaction temperature and the like and cannot be unconditionally stated, but the reaction is usually completed in about 0.1 to 24 hours.
The target compound obtained in each of the above reactions can be easily isolated from the reaction mixture by a commonly used isolation means, for example, an organic solvent extraction method, a chromatography method, a recrystallization method, a distillation method, or the like. Further, it can be purified by ordinary purification means.

Reaction equation 6

[In the formula, R ₈ indicates a hydrogen atom or C _1-6 alkyl group, and R ₉ indicates a hydrogen atom, C _1-6 alkyl group, C _1-6 alkoxy group, C _1-6 haloalkyl group, C _{2 -6} alkenyl group, C _2-6 haloalkyl group, C _2-6 alkynyl group, C _2-6 haloalkynyl group, hydroxy C _1-6 alkyl group, C _1-6 alkoxy C _1-6 alkyl group, C _{3 -6} cycloalkyl group, C _3-6 cycloalkyl C _1-6 alkyl group or benzyl group, or R ₈ and R ₉ are bonded to each other, and R ₈ and R ₉ are bonded to nitrogen. Together with the atom, it may form a saturated or unsaturated 4- to 7-membered ring. R ₃ , R ₄ , R ₅ , R ₁₀ , X and n are as defined above. ]
In the method represented by the reaction formula 6, the hydrazone derivative represented by the formula (11) is obtained by reacting the hydrazone derivative represented by the formula (12) with the amine derivative represented by the formula (13). Can be manufactured.

As the solvent used in the amination reaction of the hydrazone compound represented by the formula (12), known solvents can be widely used as long as they are inert to the reaction. Examples of such a solvent include an aliphatic or alicyclic hydrocarbon solvent such as hexane, cyclohexane and heptane, an aromatic hydrocarbon solvent such as benzene, chlorobenzene, toluene and xylene, methylene chloride and 1,2-. Dichloroethane, halogenated hydrocarbon solvents such as chloroform, alcohol solvents such as methanol and ethanol, ester solvents such as methyl formate, ethyl formate, methyl acetate and ethyl acetate, ketone solvents such as acetone and methyl ethyl ketone, N, N Examples thereof include amide solvents such as dimethylformamide, nitrile solvents such as acetonitrile and propionitrile, and aprotonic polar solvents such as N-methylpyrrolidone and N, N'-dimethylimidazolinone. One of these solvents can be used alone, or two or more of these solvents can be mixed and used as required.
The amine derivative (13) can be used in an amount usually 1 to 5 equivalents, preferably 1 to 2.5 equivalents, relative to the hydrazone derivative represented by the formula (12).
The reaction can usually be carried out within the range of −78 ° C. to the boiling point temperature of the solvent used, and it is preferable to carry out the reaction at 0 ° C. to the boiling point temperature.
The reaction time varies depending on the reaction temperature and the like and cannot be unconditionally stated, but the reaction is usually completed in about 0.1 to 24 hours.
The target compound obtained in each of the above reactions can be easily isolated from the reaction mixture by a commonly used isolation means, for example, an organic solvent extraction method, a chromatography method, a recrystallization method, a distillation method, or the like. Further, it can be purified by ordinary purification means.

Reaction equation 7

[In the equation, R ₁ indicates a hydrogen atom, and R ₃ , R ₄ , R ₅ , R ₈ , R ₉ , R ₁₀ , X and n are as defined above. ]
In the method represented by the reaction formula 7, the hydrazone derivative represented by the formula (11) can be produced by reacting the hydrazone derivative represented by the formula (7) with the acetal derivative (19).

As the solvent used in the reaction between the hydrazone compound represented by the formula (7) and the acetal derivative represented by the formula (19), known solvents are widely used as long as they are inert to the reaction. can do. Examples of such a solvent include an aliphatic or alicyclic hydrocarbon solvent such as hexane, cyclohexane and heptane, an aromatic hydrocarbon solvent such as benzene, chlorobenzene, toluene and xylene, methylene chloride and 1,2-. Dichloroethane, halogenated hydrocarbon solvents such as chloroform, alcohol solvents such as methanol and ethanol, ester solvents such as methyl formate, ethyl formate, methyl acetate and ethyl acetate, ketone solvents such as acetone and methyl ethyl ketone, N, N Examples thereof include amide solvents such as dimethylformamide, nitrile solvents such as acetonitrile and propionitrile, and aprotonic polar solvents such as N-methylpyrrolidone and N, N'-dimethylimidazolinone. One of these solvents can be used alone, or two or more of these solvents can be mixed and used as required.
Examples of the acetal derivative (19) used in the iminization reaction of the hydrazone compound represented by the formula (7) include N, N-dimethylformamide dimethylacetal and the like.
The acetal derivative (19) can be used in an amount usually 1 to 10 equivalents, preferably 1 to 5 equivalents, relative to the hydrazone derivative represented by the formula (7).
The reaction can usually be carried out within the range of −78 ° C. to the boiling point temperature of the solvent used, and it is preferable to carry out the reaction at 0 ° C. to the boiling point temperature.
The reaction time varies depending on the reaction temperature and the like and cannot be unconditionally stated, but the reaction is usually completed in about 0.1 to 24 hours.
The target compound obtained in each of the above reactions can be easily isolated from the reaction mixture by a commonly used isolation means, for example, an organic solvent extraction method, a chromatography method, a recrystallization method, a distillation method or the like. Further, it can be purified by ordinary purification means.

Reaction equation 8

[In the equation, L indicates a leaving group such as a _{halogen atom, TsO-, CH 3} SO _3- , CF ₃ SO _3- , CH ₃ OSO _3- _{, and R 4} is defined above except for a hydrogen atom. Indicates a substituent, R ₁ , R ₃ , R ₅ , X and n are as defined above. ]
In the method represented by the reaction formula 8, the hydrazone derivative represented by the formula (3) is a hydrazone derivative represented by the formula (20) and an alkylating agent represented by the formula (6). It can be produced by reacting in an inert solvent in the presence or absence of a base.

As the solvent used in the alkylation reaction of the hydrazone derivative represented by the formula (20), known solvents can be widely used as long as they are inert to the reaction. Examples of such a solvent include an aliphatic or alicyclic hydrocarbon solvent such as hexane, cyclohexane and heptane, an aromatic hydrocarbon solvent such as benzene, chlorobenzene, toluene and xylene, methylene chloride and 1,2-. Dichloroethane, halogenated hydrocarbon solvents such as chloroform, alcohol solvents such as methanol and ethanol, ester solvents such as methyl formate, ethyl formate, methyl acetate and ethyl acetate, ketone solvents such as acetone and methyl ethyl ketone, N, N Examples thereof include amide solvents such as dimethylformamide, nitrile solvents such as acetonitrile and propionitrile, and aprotonic polar solvents such as N-methylpyrrolidone and N, N'-dimethylimidazolinone. One of these solvents can be used alone, or two or more of these solvents can be mixed and used as required.
Examples of the alkylating agent (6) used in the alkylation reaction of the hydrazone compound represented by the formula (20) include methyl iodide, ethyl iodide, allyl bromide, propargyl bromide, 1-bromo-2-butyne, and the like. Examples thereof include methyl bromoacetate, benzyl bromide, dimethyl sulfate and the like.
Such an alkylating agent can be used in an amount usually 1 to 10 equivalents, preferably 1 to 2 equivalents, relative to the hydrazone derivative represented by the above formula (20).
The reaction can usually be carried out within the range of −78 ° C. to the boiling point temperature of the solvent used, and it is preferable to carry out the reaction at 0 ° C. to the boiling point temperature.
The reaction time varies depending on the reaction temperature and the like and cannot be unconditionally stated, but the reaction is usually completed in about 0.1 to 24 hours.
The target compound obtained in each of the above reactions can be easily isolated from the reaction mixture by a commonly used isolation means, for example, an organic solvent extraction method, a chromatography method, a recrystallization method, a distillation method, or the like. Further, it can be purified by ordinary purification means.

Reaction equation 8

[In the equation, L indicates a leaving group such as a _{halogen atom, TsO-, CH 3} SO _3- , CF ₃ SO _3- , CH ₃ OSO _3- _{, and R 1} is defined above except for a hydrogen atom. Indicates a substituent, R ₃ , R ₄ , R ₅ , X and n are as defined above. ]
In the method represented by the reaction formula 8, the hydrazone derivative represented by the formula (2) is a hydrazone derivative represented by the formula (3) and an alkylating agent represented by the formula (4). It can be produced by reacting in an inert solvent in the presence or absence of a base.

As the solvent used in the alkylation reaction of the hydrazone derivative represented by the formula (3), known solvents can be widely used as long as they are inert to the reaction. Examples of such a solvent include an aliphatic or alicyclic hydrocarbon solvent such as hexane, cyclohexane and heptane, an aromatic hydrocarbon solvent such as benzene, chlorobenzene, toluene and xylene, methylene chloride and 1,2-. Dichloroethane, halogenated hydrocarbon solvents such as chloroform, alcohol solvents such as methanol and ethanol, ester solvents such as methyl formate, ethyl formate, methyl acetate and ethyl acetate, ketone solvents such as acetone and methyl ethyl ketone, N, N Examples thereof include amide solvents such as dimethylformamide, nitrile solvents such as acetonitrile and propionitrile, and aprotonic polar solvents such as N-methylpyrrolidone and N, N'-dimethylimidazolinone. One of these solvents can be used alone, or two or more of these solvents can be mixed and used as required.
Examples of the alkylating agent (4) used in the alkylation reaction of the hydrazone compound represented by the formula (3) include methyl iodide, ethyl iodide, allyl bromide, propargyl bromide, 1-bromo-2-butyne, and the like. Examples thereof include methyl bromoacetate, benzyl bromide, dimethyl sulfate and the like.
Such an alkylating agent can be used in an amount usually 1 to 10 equivalents, preferably 1 to 2 equivalents, relative to the hydrazone derivative represented by the above formula (3).
The reaction can usually be carried out within the range of −78 ° C. to the boiling point temperature of the solvent used, and it is preferable to carry out the reaction at 0 ° C. to the boiling point temperature.
The reaction time varies depending on the reaction temperature and the like and cannot be unconditionally stated, but the reaction is usually completed in about 0.1 to 24 hours.
The target compound obtained in each of the above reactions can be easily isolated from the reaction mixture by a commonly used isolation means, for example, an organic solvent extraction method, a chromatography method, a recrystallization method, a distillation method, or the like. Further, it can be purified by ordinary purification means.

Table 1 shows the representative compounds of the hydrazone derivative represented by the formula (1) of the present invention, Table 2 shows the representative compounds of the hydrazone derivative represented by the formula (7) of the present invention, and Table 2 shows the representative compounds of the hydrazone derivative represented by the formula (7) of the present invention. Typical compounds of the ketone derivative represented by the formula (16) are exemplified in Table 3, but the scope of the present invention is not limited by these exemplified compounds.
In Tables 1 to 3, the physical properties or melting point (° C.) are shown, "n-" is normal, "s-" is secondary, "t-" is tertiary, and "i-". "" Indicates iso, "c-" indicates cyclo, "Me" indicates a methyl group, "Et" indicates an ethyl group, "Pr" indicates a propyl group, "Bu" indicates a butyl group, and ""Ph" indicates a phenyl group. In addition, * 1 in the table indicates that -CH = CH-CH = CH- is bonded to the 3- and 4-positions of the phenyl group. * 2 in the table indicates that -CH = CH-CH = CH is bonded to the 2- and 3-positions of the phenyl group.
In addition, A-84 and A-85 are isomers of each other.

General formula (1)

General formula (7)

General formula (16)

The compounds of the present invention can be used in agriculture, indoors or in forests for the prevention and extermination of organisms that are harmful to livestock or in various situations such as hygiene. Specific usage situations, target pests, and usage methods are shown below, but the content of the present invention is not limited thereto.
The compound of the present invention represented by the above formula (1) is an agricultural crop, for example, edible crops (wheat such as rice, barley, wheat, rye, oat, corn, horse bell 薯, sweet potato, satoimo, soybean, red bean, sora bean. , Endo beans, green beans, beans such as peanuts, etc.), vegetables (cabbage, white vegetables, radish, buds, broccoli, potash flowers, komatsuna, etc. Kinds, eggplants, tomatoes, peppers, peppers, okura, spinach, lettuce, bricks, carrots, gobos, garlic, onions, onions, etc.), mushrooms (shitake, mushrooms, etc.), fruit trees / fruits (apples, apples, etc.) Citrus, pears, grapes, peaches, plums, cherry peaches, peaches, chestnuts, almonds, bananas, strawberries, etc.), fragrances and other appreciation crops (lavender, rosemary, thyme, parsley, pepper, ginger, etc.) , Tea, vegetables, sugar cane, hops, cotton, hemp, olives, rubber, coffee, etc.), grass and feed crops (timothy, clover, alfalfa, corn, sorghum, orchardgrass, rice grass, bean grass, etc.) , Crop (Koryo turf, bentgrass, etc.), forest trees (beans, beans, pine, hiba, cedar, fox, etc.) and ornamental plants (crops, roses, carnations, orchids, herbs, flowers, ginkgo, etc.) Harm to arthropods, soft animals, nematodes, and fungi and bacteria such as fungi, deformed fungi, bacterial phylum, and actinomycetes that damage garden trees such as cherry blossoms and aoki. It can also be used to control organisms. Specific pests include the following.

Lepidoptera of the phylum Arthropod, for example, Helicoverpa armigera, Heliothis spp., Agrotis segetum, Autographa nigrisigna, Tricho ), Yotoga (Mamestra brassicae), Shiroichimojiyoto (Spodoptera exigua), Hasmonyoto (Spodoptera litura), etc. honmai), Midarekakumonhamaki (Archips fuscocupreanus), Chahamaki (Homona magnanima), Chanohosoga (Caloptilia theivora), Nashihimeshinkui (Grapholita molesta), etc. malinella), Momohamoguriga (Lyonetia clerkella), etc., Lepidoptera chinensis (Phyllocnistis citrella), etc. , Stahmopoda masinissa, etc., Pectinophora gossypiella, etc., Carposina niponensis, Lepidoptera, Nponensis, Cossus, jezoensis, etc. , Iraga family Iraga (Monemaflavecens), Hirohelia oila (Parasa lepida), Himekuroiraga (Scopelodes con) Tracus, etc., Crambi suppressalis, Scirpophaga incertulas, Cnaphalocrocis medinalis, Helllula undalis, Conogethes punctiferlis, Conogethes punctiferlis, etc. Pyraloid moth (Parapediasia teterrella), Pyraloid moth (Locastra muscosalis), Parnara guttata, Pyraloid moth, Namiageha (Papilio xuthus), etc. Lyraloid moth (Lampides boeticus), Orgyraloid moth (Ascotis selenaria), Crambius convolvuli (Agrius convolvuli), Phalera flavescens, etc. Neustrium testaceum, etc., Saturnia japonica, etc., Chadokuga (Euproctis pseudoconspersa), Orgyia thyellina, Akamondokuga (Telochurus recens approximans), etc. Adults, larvae and eggs such as American white-spotted moth (Hyphantria cunea), Grapeberry moss (Endopiza viteana), Kodlinga (Laspeyresia pomonella);

Coleoptera, for example, Anomala cuprea, Popilla japonica, Oxycetonia jucunda, Anomala geniculata, etc., Anomala geniculata, etc. , Beetle family Melanotus fortnumi, etc., Weevil family Nijuyahoshi tentou (Epilachna vigintioctopunctata), etc. Aulacophora femoralis), root worm species (Diabrotica spp.), Chrysalis weevil (Phyllotreta striolata), beetle leaf beetle (Cassida nebulosa), daikon leaf beetle (Phaedon brassicae), rice weevil (Oulema weevil) vest ), Etc., Chrysomelidae weevil (Rhynchites heros), etc., Chrysomelidae weevil (Cylas formicarius), etc. Adults, larvae and eggs such as grandis), leaf beetle (Sphenophrus venatus vestitus), etc.

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

Homoptera of the order Hemiptera, for example, Platypleura kaempferi of the semi-family, Arboridia apicalis of the aphid family, Empoasca onukii, cinc-onukii , Taiwan Tsumaguro Yokobai (Nephotettix virescens), etc., Himetobiunka (Laodelphax striatellus), Tobiirounka (Nilaparvata lugens), Sejirounka (Sogatella furcifera), etc. Various biotypes of aphids (Diaphorina citri), aphids of the aphid family (Aleurocanthus spiniferus), silver leaf aphids (Bemisia argentifolii), tobacco aphids (Bemisia tabaci), mikan konajirami (Dialeurodesci) Aphis citricola, Aphis craccivora, Wata aphid (Aphis gossypii), Potato aphid aphid (Aphis gossypii), Potato aphid (Aphis gossypii) ), Komikan aphid (Toxoptera aphid), Mikan black aphid (Toxoptera citricidus), Niwatokohigenaga aphid (Aulacorthum magnoliae), Nasia bramushi (Schizaphispiricola), Nashimidrio aphid (Nippolachnus piri) Momokofuki aphid (Hyalopterus pruni), Kikugi care aphid (Pleotrichophorus chrysanthemi), Kikuhimehigenagaabramushi (Macrosiphoniella sanborni), Soramamehigenagaabramushi (Megoura crassicauda), Ibarahigenagaabramushi (Sitobionibarae), Tulip scale insect (Macrosiphum) persicae), Okabonoakabramushi (Rhopalosiphum rufiabdominalis), Wheat scale insect (Rhopalosiphum padi), Wheat scale insect (Sitobion akebiae), Ringo cotton scale insect (Eriosoma lanigerum), etc. Scale insects (Pseudococcus comstocki), scale insects (Phenacoccus viburnae), Fujikonakaigaram (Phenacoccus kraunhiae), scale insects (Ceroplastes ceriferus), scale insects (Ceroplastes) Adults, larvae and eggs of scale insects (Aonidiella aurantii), pear scale insects (Comstockaspis perniciosa), scale insects (Pseudaulacaspis pentagoa), scale insects (Unaspis yanonensis);

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

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

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

Adults, larvae and eggs of the Collembola, Collembola, for example, the Collembola, Sminthurus viridis, and Onychiurus matsumotoi, the phylum arthropod. Adults, larvae and eggs of the Collembola (Isopada), such as the Armadillidium vulgare of the pill bug family;
Acari of the phylum Spider Mite, for example, Polyphagotarsonemus latus, Phytonemus pallidus, Penthaleus major, etc. lewisi), Minamihime spider mite (Brevipalpus phoenicis), spider mites (Panonychus citri), apple spider mite (Panonychus ulmi), Nami spider mite (Tetranychus urticae), Kanzawa spider mite (Tetranychus kanzawai) Oligonychus ununguis), Kikubira spider mite (Bryobia eharai), Miyakeake spider mite (Eotetranychus kankitus), Clover spider mite (Bryobia praetiosa), etc. ), Eriophyes chibaensis, Aceria tulipae, Colomerus vitis, Aculus fockeui, Calacarus carinatus, etc. Adults, larvae and eggs such as robini);

Primitive string tongues (Architaenioglossa) of the molluscs, such as Pomacea canaliculata, Plumonata, such as Achatina fulica, Slugs. Slugs (Meghimatium bilineatum), Keelback slugs (Milax gagates), Keelback slugs (Lehmannina valentiana), Keelback slugs (Acusta despecta sieboldiana), etc.
Tylenchida of the C. elegans, for example, Ditylenchus destructor of the family C. elegans, Tylenchorhynchus claytoni of the family C. elegans, etc. ), Nematode nematode (Pratylenchus coffeae), C. elegans (Helicotylenchus dihystera), C. elegans (Globodera rostochiensis), C. Nematodes (Criconema jaejuense), etc., C. elegans (Nothotylenchus acris), C. elegans (Aphelecchoides fragarriae), etc .; .), Yumihari nematode (Trichodorus sp.), Etc. of the family Trichodolus family;
Fungi and bacteria such as Myxomycota, Myxomycota, Bacteriomycota, Actinomycota.

Specific examples of the diseases to which the compound of the present invention represented by the above formula (1) can be applied include rice blast (Pyricularia oryzae), sesame leaf blight (Cochliobolus miyabeanus), and blight (Rhizoctonia solani). ), Pantoea ananatis, Acidovorax avene subsp. Avenae, Pseudomonas fuscovaginae, Xanthomonas oryzae pv. Oryzae, Burkholderia plantari Udonko disease (Erysiphe graminis), Fusarium head blight (Gibberella zeae), Fusarium head blight (Puccinia striiformis, P. graminis, P. recondita, P. Hordei), Snow rot (Typhula sp., Micronectriella nivalis) , Naked scab (Ustilago tritici, U. nuda), Namagusa scab (Tilletia caries), Eye print disease (Pseudocercosporella herpotrichoides), Cloud-shaped disease (Rhynchosporium secalis), Leaf blight (Septoria tritici), Fusarium (Leptia) ), Pyrenophora teres, Hellminthosporium zonatum Ikata, Pseudomonas syringae pv. Japonica, etc .; Black spot disease (Diaporthe citri), Fusarium head blight (Elsinoe fawcetti) Diseases (Penicillium digitatum, P. italicum), brown rot (Phytophthora citrophthora ,, P. nicotianae), scab (Phyllosticta citricarpa), etc .; (Podosphaera leucotricha), spot foliar disease (Alternaria mali), scab (Venturia inaequ) alis), black spot disease (Mycospherella pomi), charcoal disease (Colletotrichum acutatum), ring-spot disease (Botryosphaeria berengeriana), gymnosporangium yamadae, monilinia fructicola, etc .; V. pirina), black spot disease (Alternaria kikuchiana), gymnosporangium haraeanum, monilinia fructigena, etc .; thigh monilinia fructicola, cladosporium carpophilum, phomopsis rot. Phomopsis sp.) Perforated bacterial disease (Brenneria nigrifluens), etc .; Black vine disease (Elsinoe ampelina), late rot (Colletotrichum acutatum), udonko disease (Uncinula necator), rust (Phakopsora ampelopsidis), black lot disease (Phakopsora ampelopsidis) Guignardia bidwellii, Plasmopara viticola, Monilinia fructigena, Cladosporium viticolum, Botrytis cinerea, Agrobacterium vitis, etc.; Gloeosporium kaki, deciduous disease (Cercospora kaki, Mycoshaerella nawae), etc .; Colletotrichum lagenarium, Sphaerotheca fuliginea, Oidiopsis taurica, vine blight Fusarium oxysporum, Pseudoperonospora cubensis, Phytophthora sp., Pythium sp., Etc.; Pseudomonas syringae pv. Lochrymans (Pseudomon asviridiflava), brown spot bacterial disease (Xanthomonas campestris pv. Cucurbitae), etc .; melon brown spot bacterial disease (Xanthomonas campestris pv. Cucurbitae), hair root disease (Agrobacterium rhizogens), cancerous disease (Streptomyces sp.), Etc.; Bacterial disease of fruit stains (Acidovorax avenae pv. Citrulli), etc .; Bacterial blight of Xanthomonas (Ralstonia solanacearum), etc .; ), Canker disease (Clavibacter michiganense subsp. Michiganense), stem scab (Pseudomonas corrugata), soft rot (Pectobacterium carotovorum subsp. Carotovorum), etc .; Black spot disease (Alternaria japonica), white spot disease (Cercosporella brassicae), soft rot (Pectobacterium carotovorum subsp. Carotovorum), etc.; Campestris), etc .; Lettuce rot (Pseudomonas cichorii, Pseudomonas viridiflava), Bacterial spot disease (Xanthomonas campestris pv. Vitians) Negi rust (Puccinia allii), etc .; glycines), black spot disease (Diaporthe phaseolorum var. Sojae), etc .; , Brown spot disease (Cercospora arachidicola), etc .; Powdery mildew (Erysiphe pisi), etc .; Sphaerotheca humuli, etc .; Tea net blast (Exobasidium reticulatum), White star disease (Elsinoe leucospila), Red burning disease (Pseudomonas syringae pv. Theae), Powdery mildew (Xanthomonas campestris pv. Theicola), etc. Disease (Alternaria longipes), powdery mildew (Erysiphe cichoracearum), charcoal disease (Colletotrichum tabacum), sticky disease (Peronospora tabacina), plague (Phytophthora nicotianae), wilt disease (Ralstonia solanacearum), cavity disease (Pectobacterium) .Carotovorum), etc .; Tensai brown spot disease (Cercospora beticola), seedling blight (Aphanomyces cochliodes), etc .; Rose scab (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa), etc.; chrysanthemi-indici), white rust (Puccinia horiana), root cancer powder (Agrobacterium tumefaciens), etc .; various crops such as eggplant, cucumber and lettuce Snow rot of turf (Pythium iwayamai, Tyohula incarnate, Fusarium nivale, Sclerotinia borealis), powdery mildew (Erysiphe graminis), faring disease (Lycoperdon perlatum, Lepista subnudo, Marasmius) eratobasidium spp.), Gaemannomyces graminis, Curvularia geniculata, Rhizoctonia solani, Pythium periplocum, Pythium vanterpoolii, Puccinia spp. Diseases (Sclerotinia homoeocarpa), etc .; Examples include bentgrass red burning disease (Pythium aphanidermatum) and charcoal sickness (Colletotrichum sp.).

The compound of the present invention represented by the above formula (1) is active indoors in buildings including ordinary houses, and damages or rots wood and its processed products such as wooden furniture, stored foods, clothing, and books. It can also be used to control arthropods and fungi that damage our lives. Specific pests include the following.

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

Lepidoptera, for example, the tinea moth (Cadra cautella), the tinea moth (Ephestia kuehniella), the Indianmeal moth (Plodia interpunctella), the clothes moth (Sitotroga cerealella), etc. Adults, larvae and eggs such as translucens and clothes moth (Tineola bisselliella);
Adults, larvae and eggs of the order Cockroach, such as the German cockroach (Blattella germanica), the German cockroach (Periplaneta fuliginosa), and the German cockroach (Periplaneta japonica); Adults, larvae and eggs such as pharaoni) and monomorium nipponense;

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

The compound of the present invention represented by the above formula (1) can also be used for controlling harmful organisms that damage or weaken trees in natural forests, artificial forests and urban green spaces. Specific pests include the following.

Arthropod phylum Insectidae, for example, Lymantriidae Sugidokuga (Calliteara argentata), Chadokuga (Euproctis pseudoconspersa), Himeshiromondokuga (Orygia recens approximans), Dokuga (Euproctis subflava), Maiga (Lymantria disp) Family Obikareha (Malacosoma neustria testacea), Matsukareha (Dendrolimus spectabilis), Tsugakareha (Dendrolimus superans), etc. (Ptycholoma lecheana circumclusana), Kurimiga (Cydia kurokoi), Sugikasaga (Cydia cryptomeriae), etc. Adults, larvae and eggs such as Parasa lepida, Scopelodes contracus, Microleon longipalpis; Family jewel beetle (Agrilus spininipennis), larvae of the family Lymantriidae (Monochamus alternatus), etc. ), Etc., Sipalinus gigas, etc., pine beetle (Tomicus piniperda), jewel beetle (Indocryphalu), etc. Adults, larvae and eggs such as Rhizopertha dominica of the family Rhyzopertha dominica, etc.;

C. Adults, larvae and eggs such as ceriferus);
Adults, larvae and eggs of the order Bee, such as the Tenthredinidae Pachynematus itoi, the Neodiprion sertifer of the Tenthredinidae, and the Dryocosmus kuriohilus of the Cecidomyiidae; Adults, larvae and eggs of Crane fly (Tipula aino), Tenthredinidae (Strobilomyia laricicola), Cecidomyiidae (Contarinia inouyei), Cecidomyiidae (Contarinia matsusintome), etc.
Adults, larvae and eggs of the arachnids of the phylum Arachnid, such as Oligonichus hondoensis, Oligonichus ununguis;
C. elegans Tyrenx, for example, Bursaphelenchus xylophilus of the family Parasitaferenchus.

The compound of the present invention represented by the above formula (1) is internal to vertebrates, particularly domestic animals and pets such as cattle, sheep, goats, horses, pigs, poultry, dogs, cats and fish, which are warm-blooded vertebrates. It can also be used to prevent, treat or control arthropods, nematodes, suckers, streaks and protozoa that parasitize or externally. In addition to the above, the target animal species include rodents such as mice, rats, hamsters and squirrels, carnivores such as ferrets, pets of birds such as ducks and pigeons, and experimental animals. Specific pests include the following.

Flies of the phylum Arthropod, for example, Culex pipiens (Tabanus rufidens), Culex pipiens (Tabanus chrysurus), Psychodidae (Musca bezzii), Psychodidae (Musca domestica), Stomoxys calcitrans, etc. Culex pipiens (Gasterophilus intestinalis), Culex pipiens (Hypoderma bovis), Culex pipiens (Oestrus ovis), Culex pipiens (Aldrichina grahami), Culex pipiens sp Etc., Human Tentsuyahosobae (Sepsis punctum), Culex pipiens (Culex pipiens molestus), Culex pipiens (Culex pipiens molestus), Culex pipiens (Culex pipiens molestus) , Sinahamadaraka (Anopheles sinensis), Culex pipiens triaeniorhynchus summorosus, Ades albopictus, etc. Adults, larvae and eggs such as Culicoides arakawae);
Adults, larvae and eggs of the order Flea, such as the flea family Cat flea (Pulex irritans), dog fleas (Ctenocephalides canis);

Lice, for example, lice (Haematopinidae suis), mallophaga (Haematopinidae eurysternus), etc. Adults, larvae and eggs such as (Menopon gallinae);
Itch mite (Varroa jacobsoni), itch mite (Haemaphysalis longicornis), itch mite (Ixodes ovatus), itch mite (Boophilus microplus), itch mite (Boophilus microplus), itch mite (Varroa jacobsoni) testudinarium), etc., Ornithonyssus sylvialum, etc., Wakumo (Dermanyssus gallinae), etc. Adults, larvae and eggs of the itch mite family Otodectes cynotis, Psoroptes communis, etc. (Knemidocoptes mutans);
C. elegans of the order C.
Ascaris suum, for example, Ascaris suum, Ascaridia galli, etc .;
Flatworm phylum fluke, for example, Schistosoma japonicum, liver tetsu, deer amphistomiasis, Paragonimus westermani, Japanese chicken egg fluke, etc.;
Tapeworms, such as foliate tapeworms, Moniezia expansus, Moniezia beneda, square tapeworms, stabbed tapeworms, raillietina cesticillus, etc .:
Root flagellates of the Protozoa phylum Flagellate, eg, Histomonas et al., Protozoan flagellates, eg Leishmania, Trypanosoma, etc., Multi-flagellate, eg Giardia, etc. Trichomonas, eg Trichomonas, etc.
Amoeba eyes of the fleshy class, such as Entamoeba;
Piroplasma subclasses of the parasitic class, such as Theilaria, Babesia, etc., Late parasitic subclasses, such as Eimeria, Plasmadium, Toxoplasma, etc.

The compound of the present invention represented by the above formula (1) is used for exterminating harmful organisms that cause direct harm or discomfort to the human body, or for maintaining public health against harmful organisms that carry or mediate pathogens. Can also be used for. Specific pests include the following.

Lepidoptera of the phylum Insect, for example, Sphrageidus similis of the family Lappet moth, Kunugia undans of the family Lappet moth, Parasa consocia of the family Lappet moth, Artona martini of the family Lappet moth. Adults, larvae and eggs;
Adults and larvae of the order Coleoptera, such as Oedemeridae (Xanthochroa waterhousei), Epicauta gorhani (Epicauta gorhani), Staphylinidae (Paederus fuscipes), etc.
Adults, larvae and eggs of the order Hymenoptera, such as Vespa simillima xanthoptera, Brachyponera chinensis, and Batozonellus annulatus, Vespidaceae;
Flies, for example, Armigeres subalbatus of the family Ceratopogonidae, Culicoides nipponensis of the family Ceratopogonidae, Chironomus yoshimatsui of the family Ceratopogonidae, Simulium nikkoense of the family Ceratopogonidae, etc. Armigeres humilis, Musca domestica, Fannia canicularis, Phromia regina, Sarcophaga peregrina, etc. Adults, larvae and eggs;
Adults, larvae and eggs of the order Flea, such as the human flea family (Pulex irritans);
Adults, larvae and eggs of the order Cockroach, such as the German cockroach (Blattella germanica), the American cockroach (Periplaneta americana), the Smokybrown cockroach (Periplaneta fuliginosa), and the German cockroach (Periplaneta japonica);
Adults, larvae and eggs of the order Orthoptera, such as Diestrammena japonica and Diestrammena apicalis of the family Cricketidae;
Adults, larvae and eggs of the order Pediculus, such as the pediculus humanus (Pediculus humanus humanus) and the pubic lice (Phthirius pubis);
Adults, larvae and eggs of Isyndus obscurus of the Reduviidae, such as Bed Bugs (Cimex lectularius), for example.

Adults, larvae and eggs of Collembola, for example, Collembola of the phylum arthropod family, for example, Hypogastrura communis of the family Collembola;
Dust mites of the phylum Arachnidae, such as Ixodes persulcatus of the Ixodidae, Ornithonyssus bacoti of the Ixodidae, Chelacaropsis moorei of the Ixodidae, and Pyemotes of the Ixodidae. Ventricosus, etc., Demodex folliculorum, etc., Dermotophagoides pteronyssinus, etc., Arachoptes scabiei, etc. ;
Authentic spiders, such as the jumping spider (Chiracanthium japonicum), the jumping spider (Heteropoda venatoria), the jumping spider (Spermophora senoculata), the Urocteridae (Pholcus) ), Etc. Adults, larvae and eggs of the jumping spider family Plexippus paykulli, Plexippus adansoni, etc.;
Adults, larvae and eggs of the order Scorpion, such as the Isometrus maculatus (Isometrus europaeus);
Adults, larvae and eggs of the order Scolopendra, such as Scolopendra subspinipes mutilans and Scolopendra subspinipes japonica;
Centipedes, such as adults, larvae and eggs such as Centipedes (Thereuronema hilgendofi);
The order Polydesmida of the arthropod phylum Myriapoda, such as adults, larvae and eggs such as Polydesmida (Oxidus gracilis) of the family Polydesmida;
Arthropods Crustaceans, such as adults, larvae and eggs of the woodlouse (Porcellio scaber) of the woodlouse family;
Clitellata zeylanica japonica, for example, Haemadipsa zeylanica japonica, etc. of the family Haemadipsa zeylanica.
Trichophyton rubrum, Trichophyton mentagrophytes, etc., Candida albicans, etc., Aspergillus fumigatus, etc., Escherichia coli, Escherichia coli, Pseudomonas aeruginosa, etc. Gram-positive bacteria such as aureus.

The compound of the present invention represented by the above formula (1) is a pest that damages agricultural crops, natural forests, artificial forests, trees in urban green areas, and ornamental plants, such as arthropods, abalone, and nematodes. It is especially valuable to control fungi. In such situations, the compounds of the invention are other active compounds, such as pesticides, acaricides, nematodes, fungicides, in their commercially useful formulations and the forms of use prepared by those formulations. It can also exist as an agent, a synergist, a plant growth regulator, a poison bait or a mixture with a herbicide.
The usage patterns include wettable powders, granule wettable powders, dry flowable agents, water solvents, emulsions, liquids, oils, flowable agents such as suspensions in water and emulsions in water, capsules, powders, granules, and fine particles. Granules, baits, tablets, sprays, fumes, aerosols, etc. can be taken. In order to obtain these dosage forms, various pesticide aids conventionally used in the technical field of agricultural and horticultural chemicals can be appropriately used. Such pesticide aids can be used, for example, for the purpose of improving the effect, stabilizing, and improving the dispersibility of agricultural and horticultural chemicals.

Examples of the pesticide auxiliary agent include carriers (diluents), emulsifiers, wettable powders, dispersants, disintegrants and the like. 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 dimethyl sulfoxide, and methylnaphthalene. , Cyclohexane, animal and vegetable oils, fatty acids and the like. Further, as the solid carrier, clay, kaolin, talc, diatomaceous earth, silica, calcium carbonate, montmorillonite, bentonite, feldspar, quartz, alumina, sawdust, nitrocellulose, starch, arabic rubber and the like can be used.
As the emulsifier and dispersant, ordinary surfactants can be used. For example, higher alcohol sodium sulfate, stearyltrimethylammonium chloride, polyoxyethylene alkylphenyl ether, lauryl betaine and other anionic surfactants can be used. , Cationic surfactant, nonionic surfactant, amphoteric surfactant and the like can be used.
Further, a wetting agent such as dialkylsulfosuccinate, a fixing agent such as carboxymethyl cellulose and polyvinyl alcohol, and a dispersant such as sodium lignin sulfonate and sodium lauryl sulfate can be used.
Of course, the compound of the present invention may be blended as an active ingredient in combination of one or more. 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 type, application method, etc. It may be appropriately determined depending on various conditions, but for example, it is about 0.5 to 20% by mass, preferably about 1 to 10% by mass, and about 1 to 90% by mass, preferably 10 for a wettable powder. It can be produced so as to contain an active ingredient of about 80% by mass, and in the case of an emulsion, about 1 to 90% by mass, preferably 10 to 40% by mass.

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

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

The compound of the present invention represented by the above formula (1) protects wood (standing wood, fallen wood, processed wood, stored wood or structural wood) from damage by insects such as termites or corns and fungi. Is also worth it. In such situations, it is possible to control wood or the soil around it by spraying / injecting / irrigating / applying oils, emulsions, wettable powders, sol agents, and spraying powders, granules, etc. can. In addition, the oils, emulsions, wettable powders, powders and the like used in this scene may be used with other active compounds such as insecticides, acaricides, nematodes, bactericides, repellents or synergists. It can also be present as a mixture, with the total amount of active ingredient compounds in these formulations 0.0001 to 95% by weight, preferably 0.005 to 10% by weight for oils, powders and granules, emulsions and wettable powders and sol. The agent may contain 0.01 to 50% by mass. When controlling arthropods or fungi, spray 0.01 to 100 g of the active ingredient compound per ^{1 m 2 on the soil or wood surface.}

The compound of the present invention represented by the above formula (1) is used when a product such as a grain, a fruit, a nut, a spice, or a tobacco is stored as it is, in a powdered state, or in a state of being mixed in the product. It can be used to protect against the damage of lepidoptera, lepidoptera, mites and fungi. Also, when storing animal products (skin, hair, wool, feathers, etc.) and plant products (cotton, paper, etc.) in a natural or converted state, from the attack of lepidoptera, beetles, stains, cockroaches, etc. It can be protected and can be protected from attacks by lepidoptera, beetles, flies and mites when storing foods such as meat and fish. In such situations, methods such as spraying oils, emulsions, wettable powders, powders, etc., installing resin transpiration agents, treating smoke agents and fumes, installing granules, tablets and poison bait, spraying aerosol, etc. Can be controlled with. In addition, these preparations can also exist as a mixture with other active compounds such as insecticides, acaricides, nematodes, fungicides, repellents or synergists, and are included in these preparations. Can contain 0.0001 to 95% by mass of the active ingredient compound in total.

The compound of the present invention represented by the above formula (1) is a disease of arthropods and fungi, humans and domestic animals that parasitize the body surface of humans and domestic animals and cause direct harm such as skin feeding or blood sucking. Value for eradicating or preventing arthropods, nematodes, suckers, streaks, protozoa, and arthropods that cause discomfort to humans There is. In such situations, a small amount of the compound of the present invention may be mixed into a meal or feed, or an appropriate orally ingestible compounded drug composition, for example, a tablet or pill containing a pharmaceutically acceptable carrier or coating substance. Oral administration as capsules, pastes, gels, beverages, medicated feeds, medicated drinking waters, medicated lotions, releaseable large pills, and other releaseable devices that are retained in the gastrointestinal tract, or sprays, powders, It can be transdermally administered as a grease, cream, ointment, emulsion, lotion, spot-on, pore-on, shampoo or the like. In order to achieve the effect in such an application, the active ingredient compound is generally contained in the preparation in an amount of 0.0001 to 0.1% by mass, preferably 0.001 to 0.01% by mass. As a method of transdermal administration or local administration, a device attached to the animal (for example, a collar, a medallion, an ear tag, etc.) for locally or systemically controlling arthropods can also be used.

Specific oral administration methods and transdermal administration methods when the compound of the present invention represented by the above formula (1) is used as an anthelmintic agent for animals such as livestock and pets or humans are shown, but are not necessarily limited to these. It's not something.
When administered orally as medicated drinking water, the beverage is usually dissolved, suspended or dispersed in a suitable non-toxic solvent or water with a suspending agent such as bentonite or a wetting agent or other excipient. be. Beverage formulations generally contain 0.01-1.0% by weight, preferably 0.01-0.1% by weight, of the active ingredient compound.
If it is desirable to administer orally in a unit-use form of a dry individual, capsules, pills or tablets containing a predetermined amount of the active ingredient are usually used. These uses are homogeneously mixed with diluents, fillers, disintegrants and / or binders such as starch, lactose, talc, magnesium stearate, vegetable rubber, etc., in which the active ingredient is appropriately finely ground. Manufactured. Such unit-use formulations can vary widely in the weight and content of the anthelmintic depending on the type of host animal being treated, the degree of infection and the type of parasite and the weight of the host.

When administered by animal feed, it can be uniformly dispersed in the feed, used as a top dressing or in the form of pellets. Usually, in order to achieve the desired antiparasitic effect, the final feed contains 0.0001-0.05% by weight, preferably 0.0005-0.01% by weight of the active ingredient compound.
Dissolved or dispersed in a liquid carrier excipient can be administered parenterally to animals by intragastric, intramuscular, intratracheal or subcutaneous injection. For parenteral administration, the active compound is preferably mixed with a suitable vegetable oil such as peanut oil, cottonseed oil. Such formulations generally contain 0.05-50% by weight, preferably 0.1-5.0% by weight, of the active ingredient compound.
It can also be administered topically by mixing with a suitable carrier such as dimethyl sulfoxide or a hydrocarbon solvent. This formulation is applied directly to the outer surface of the animal by spraying or direct injection.
In addition, the compound of the present invention represented by the above formula (1) has latent pests as an insecticide for arthropods that directly cause harm or arthropods that are mediators of diseases. Spraying / injecting / irrigating / applying oils, emulsions, wettable powders, etc., spraying powders, smoky agents, mosquito-removing incense, self-burning smoke agents, chemical reaction smoke agents, etc. Heated fuming agents such as, smoking agents such as fogging, treatment of ULV agents, installation of granules, tablets and poison bait, or water channels such as floating powders and granules, wells, reservoirs, reservoirs and other running or stagnant water. It can also be used by a method such as adding dripping to. Furthermore, it is possible to control mosquitoes, which are also agricultural and forest pests, in the same manner as described above, or for flies, etc., they should be mixed in the feed of livestock and mixed with feces. For mosquitoes and the like, a method of volatilizing them into the air with an electric mosquito catcher or the like is also effective. In addition, the pharmaceutical product in these usage forms may exist as a mixed agent with other active compounds such as pest control agent, mite control agent, nematode control agent, disease control agent, repellent or synergistic agent. , The active ingredient compound is contained in these formulations in a total amount of 0.0001 to 95% by mass.

The compound of the present invention represented by the above formula (1) can also exist as a mixing agent with other active compounds. Especially for controlling pests such as arthropods, abdominal feet, and nematodes that damage plants when used in combination with a compound (insecticide) having pest control activity, mite control activity, or nematode control activity. On the other hand, the number of pests to be controlled can be expanded, and synergistic effects such as reduction of the amount of drug can be expected. Specific examples of the active compound 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, methidathion. monocrotophos, naled, oxideprofos, parathion, phenthoate, phosalone, pyrimiphos-methyl, pyridafenthion, profenofos, prothios. ), Propaphos, pyraclofos, salithion, sulprofos, thiometon, tetrachlorvinfos, trichlorphon, vamidothion, etc .;
Carbamate agents such as alanycarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, furathiocarb. (Furathiocarb), isoprocarb, metomyl, metolcarb, pyrimicarb, propoxur, thiodicarb, etc .;
Organochlorin agents such as aldrin, chlordane, DDT (p, p'-DDT), endosulfan, lindane, etc .;

Pyrethroids such as acrinathrin, allethrin, bifenthrin, cycloprothrin, cyfluthrin, cyhalothrin, cyphenothrin, cypermethrin, delta. deltamethrin, ethofenprox, fenpropathrin, fenvalerate, flucythrinate, flufenprox, fluvalinate, furamethrin, halophen Prox (halfenprox), imiprothrin (imiprothrin) permethrin (permethrin), phenothrin (phenothrin), prallethrin (prallethrin), pyrethrin (pyrethrins), resmethrin (resmethrin), cypermethrin (silafluofen), tefluthrin (tefluthrin) Transfluthrin, etc .;
Neonicotinoid agents such as acetamiprid, clothianidin, dinotefran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, etc .;
Diamide agents such as chlorantraniliprole, cyantraniliprole, cyclaniliprole, flubenziamid, 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 phenylbenzoylurea and diacylhydrazines, such as chlorfluazuron, diflubenzuron, flufenoxuron, hexaflumuron, lufenuron, novallon. (Novaluron), teflubenzuron, triflumuron, buprofezin, chromafenozide, halofenozide, methoxyfenozide, tebufenozide, tebufenozide, cyromazine, etc.
Juvenile hormone agents such as diofenolan, fenoxycarb, hydroprene, methoprene, 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 agent, etc.;
Pesticide-derived substances derived from natural substances, such as anabasine, azadiractin, deguelin, decanolyoctanoylglycerol, hydroxy propyl ester, soy lecithin, and nicotine. ), Nornicotine, oreic acid sodium salt, petroleum oil, propylene glycol monolaurate, rape oil, rotenone, sorbitan fatty acid ester () Sorbitan fatty acid ester), starch (starch), etc .;
Other pesticides include, for example, afidpyropen, benzpyrimoxan, broflanilide, chlorfenapyr, diafenthiuron, dicloromezotiaz, dimpropyridaz. , DBEDC (Dodecylbenzenesulphonic acidbisethylenediamine copper [II] salt), flonicamid, flometoquin, flufenerim, flupyradifurone, flupyrimin, fluralaner, fluralaner ), Hydramethylnon, indoxacarb, isocycloseram, metaflumizone, metaldehyde, nicotin sulfate, oxazosulfyl, pimetrodin (Pymetrozine), pyridalyl, pyrifluquinqzon, spirotetramat, sulfoxaflor, tolfenpyrad, triazamate, triflumezopyrim, tycropyrazopyrim etc;

Acaricides such as acequinocyl, acynonapyr, amidoflumet, amitraz, azocyclotin, benzoximate, bifenazate, binapacryl, phenisobromo. Rate (bromopropylate), chinomethionat, clofentezine, cyenopyrafen, cyflumetofen, cyhexatin hydroxide, dicofol, dienochlor, ethoxazole , Fenazaflor, fenazaquin, fenbutatin oxide, fenothiocarb, fenpyroximate, fluacrypyrim, hexythiazox, polymididifen Propargite, pyflubumide, pyridaben, spirodiclofen, spiropidion, spiromesifen, tebufenpyrad, tetradifon and flupentiophenox. )etc:
Nematodes such as aluminum phosphide, benclothiaz, cadusafos, ethoprophos, fluazaindolizine, fluensulfone, fosthiazate, frusthiazate. furfural, imicyafos, levamisol hydrochloride, mesulfenfos, metam-ammonium, methyl isothiocyanate, moranteltartarate, oxamyl, thioxazafen, etc. ;
Poisonous baits such as chlorphacinone, cowatetralyl, diphacinone, sodium fluoracetate, warfarin and the like can be mentioned.

The compound of the present invention represented by the above formula (1) can also exist as a mixed agent with an active compound other than the compound having pest control activity, mite control activity or nematode control activity. In order to control diseases and / or weeds that occur at the same time as the time of use, by using it in combination with a compound having bactericidal activity, herbicidal activity or plant growth regulating activity, the control labor can be reduced and the amount of drug can be reduced. Synergistic effects can also be expected. Further, by using it in combination with a repellent or a synergistic agent, a more effective control effect such as a synergistic effect can be expected.

As a specific example of the active compound, a disease control agent, for example,
DD (1,3-dichloropropene), acibenzolar-S-methyl, aldimorph, ametoctradin, amisulbrom, andoprim, anilazine, azaconazole , Azoxystrobin, basic copper sulfate, benodanil, benomyl, benthiavalicarb-isopropyl, benthiazole, bitertanol , Bixafen, blasticidin S, boscalid, bromuconazole, calcium carbonate, buthiobate, calcium polysulfide, captafol ( captafol, captan, carbendazim, carboxin, carpropamid, chinomethionat, chlorfenazole, chlorofenazole, chloropicrin, chlorothalonil. , Chlozolinate, DBEDC (complex of bis (ethylenediamine) copper-bis- (dodecylbenzenesulfonic acid)), cupper hydroxide, copper nonylphenol sulfonate, copper chloride (copper) oxychloride), cyazofamid, cyflufenamid, cymoxanil, cyproconazole, cyprodin il), dazomet, diclobutrazol, dichlofluanid, dichlone, dichlocymet, dichromezine, diethofencarb, diphenoconazole diflumetorim, dimethomorph, dimoxystrobin, diniconazole, diniconazole-M, dithane-stainless, dithianon, dodine, echlomezole ), Edifenphos, enestrobin, epoxiconazole, etaconazole, ethaboxam, extract from mushroom, famoxadone, fenamidone ), Fenarimol, fenbuconazole, fenfuram, fenhexamid, fenoxanol, fenpiclonil, fenpropidin, fenpyrazamine, ferimzone (Ferimzone), fluazinam, flumetover, flumorph, fluopicolide, fluopyram, fluoroimide, fluotrimazole, fluoxastrobin , Fluquinconazole, flusulfamide, flutolanil, fluxapyroxad, holpet (fo) lpet, fosetyl-AL, fthalide, fuberidazole, fludioxonil, flusilazole, flutianil, flutriafol, furametpyr, fluametpyr, fluametpyr (Furconazole), guazatine, hexaconazole, hydroxyioxazole, hymexazol, imazalil, imazalil sulfate, imibenconazole, iminoctadine acetate Salt (iminoctadine acetate), iminoctadine-DBS, ipconazole, IBP (iprobenfos), iprodione, iprovalicarb, isofetamid, isofetamid, isoprothiolane ), Isotianil, kasugamycin, kresoxim-methyl, mancozeb, mandipropamid, maneb, manzeb, mepanipyrim, mepanipyrim, mepanipyrim , Metalaxyl, metam-ammonium, metam-sodium, metconazole, metasulfocarb, methyl bromide, methylisothiocyanate, methomi Nostrobin (metominostrobin), Metrafenone (metrafenone), Mildiomycin (mildiomycin), Microbutanil (myclobutanil), Organic Sulfur Nickel Salt (nick) el dimethyldithiocarbamate, nuarimol, orysastrobin, oxadixyl, oxathiapiprolin, oxine-copper, oxolinic acid, oxpoconazole fumarate (oxolinic acid) oxpoconazole fumarate, oxycarboxin, oxytetracycline, pebulate, pefurazoate, penconazole, pencycuron, penflufen, penthiopyrad, picalbutra Zox (picarbutrazox), picoxystrobin, piperalin, polycarbamate, polyoxin-B, polyoxin complex (polyoxins), potassium hydrogen carbonate (potassium hydrogen carbonate), probenazole ( probenazole, prochloraz, procymidone, propamocarb, propiconazole, propineb, proquinazid, prothioconazole, pyraclostrobin, pyraclostrobin. Tostrobin (pyrametostrobin), pyraoxystrobin (pyraoxystrobin), pyrazophos (pyrazophos), pyribencarb (pyribencarb), pyridinitrile (pyridinitril), pyrifenox (pyrifenox), pyrimethanil (pyrimethanil), pyriophenone (pyriofenone), pyrokilone (pyriofenone) (Quinoxyfen), quintozene, sedaxane, silver (silver), simeconazole (sime) conazole, sodium hydrogen carbonate, sodium hypochlorite, spiroxamine, streptomycin, sulfur, tebfloquin, tebuconazole, tecloftalam ), Terbinafine, tetraconazole, thiabendazole, thiadiazin, thifluzamide, thiophanate, thiophanate-methyl, thiram, tiadil , Tolclofos-methyl, tolprocarb, tolylfluanid, triadimefon, triadimenol, trilopyricarb, tricyclazole, tridemorph Trifloxystrobin, triflumizole, triforine, triticonazole, uniconazole-P, validamycin (-A), vinclozolin, Examples thereof include zarilamid, zinc sulfate, zineb, ziram, and zoxamide.

As a compound having herbicidal activity, for example,
Aclonifen, acifluofen-sodium, alachlor, alloxydim, amiclabazone, amidosulfuron, anilofos, ashlam, 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, diclohop-methyl, diflufenican, dimefuron, dimetamethrin (Dimethametryn), dinoterb, diquat, diuron, esprocarb, ethiozin, ethofumesate, ethoxysulfuron, etobenzanid, etobenzanid Ethyl (fenoxaprop-P-ethyl), fentrazamide, flucarbazone, flufenacet, flurtamone, fluthiaset methyl (fl) uthiacet-methyl, foramsulfuron, glufosinate-ammonium, glyphosate-isopropyl amine, glyphosate-trimesium, imazapyr, imazapyr, imazosulfuron Indanofan, iodosufluron, ioxynil-octanoate, isoproturon, isoxadifen, isoxaflutole, lactofen, linuron, mefenat ), Mesosulfuron, metamitron, metabenzthiazuron, metoslam, metribuzin, napropamide, neburon, oxadiargyl, oxadiazon. , Oxaziclomefone, paraquat, pendimethalin, pentoxazone, phenmedipham, pretilachlor, propoxycarbazone, prosulfocarb, pyracronyl. (Pyraclonil), pyraflufe n-ethyl, pyrazolate, pyrazosulfuro n-ethyl, pyribuchicarb, pyriftalid, pyriminobac-methyl, kizaro Quizalofop-ethyl, sethoxydim, simazine, sulcotrion ), Sulfentrazone, thenylchlor, triaziflam, tribufos and the like can be exemplified.

Further, as a compound having a plant growth regulating action, for example,
1-naphthylacetic acid, 4-CPA (4-CPA), benzylaminopurine (6-benzylaminopurine), butralin, calcium chloride, calcium formate, peroxidation Calcium peroxide, calcium sulfate, chlormequat chloride, choline, cyanamide, cyclanilide, daminozide, decyl alcohol, dichlorprop ( dichjoprop, ethephon, ethychlozate, flurprimidol, forclorfenuron, gibberellic acid, indolebutyric acid, hydrazide potassium maleate salt, mefenpyr, mepiquat chloride, oxine sulfate, 8-hydroxyquinoline sulfate, paclobutrazol, paraffin, prohexadione -Calcium), prohydrojasmon, thidiazuron, trinexapac, uniconazole-P, wax, etc. can also be mixed and used.
Repellents For example, capsaicin, carane-3,4-diol, citronellal, deet, dimethyl phthalate, hinokitiol, limonene. , Linalool, menthol, menthone, naphthalene, thiram, etc .;
Colytic agents such as methylenedioxynaphthalene, naphthyl propynyl ether, nitrobenzyl thiocyanate, octachlorodipropyl ether, pentynyl phthalimide, phenyl salioxon, piperonil butoxide, safrole, sesamex, sesamin, sulfoxide, triphenyl phosphate, verbutin And so on.

The compound of the present invention is used as a biopesticide, for example, cytoplasmic polyhedrosis virus (CPV), insect pox virus (Entomopox virus, EPV), granulosis virus (GV), nuclear polyhedron virus (GV), nuclear polypesticide (Cytoplasmic polyhedrosis virus, CPV). Viral preparations such as Nuclear polyhedrosis virus (NPV), Beauveria bassiana, Beauveria brongniartii, Monocrossporium phymatophagum, Pekilomyces phymatophagum, Pekiromyces fumosoroseus ), Steinernema carpocapsae, Steinernema glasseri, Steinernema kushidai, Verticillium lecanii, etc. Micropesticide, Agrobacterium radiobactor, Bacillus subtilis, non-pathogenic Erwinia carotovora, non-pathogenic Fusarium oxysporum, Pseudomonas CAB-02 Pseudomonas CAB-02), Pseudomonas fluorescens, Talaromyces flavus, Trichoderma atroviride, Trichoderma atroviride, Trichoderma lignorum, etc. -Similar effects can be expected by using it in combination with biopesticide used as a herbicide such as Campestris.

Further, as biological pesticides, for example, Amblyseius californicus, Amblyseius cucumeris, Amblyseius degenerans, Aphidius colemani, Aphidius colemani, Aphidius colemani, Aphidius colemani, Aphidius colemani, Aphidius colemani (Chrysoperia carnea), Amblyseius colemina (Dacnusa sibirica), Isaea Himekobachi (Diglyphus isaea), Onsitsutsuyakobachi (Encarsiaformosa), Sabakutsuyakobachi (Eretmocerus eremicus) , Kanmurihimekobachi (Hemiptarsenus varicornis), Hamogurimidorihimekobachi (Neochrysocharisformosa), Namihimehanakamemushi (Oriussauteri), Tairikhimehanakamemushi (Oriusstrigicollis) Natural enemy creatures such as Piocorisvarius, codlelure, cuelure, geraniol, gyptol, liblure, looplure, methyleugenol, orfralure , Peachflure, phycilure, pyrimalure, terpentine, etc. can also be used in combination with pheromone agents.

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

Example 1
1,1,1-Trifluoro-N- [1- (2-formyl-2-methylhydrazilidene) -1-phenylpropan-2-yl] -Synthesis of N-methylmethanesulfonamide (Compound No .: A) -Four)
Synthesis of 1-1: 1,1,1-trifluoro-N- (1-oxo-1-phenylpropan-2-yl) methanesulfonamide (Compound No .: C-1)
Potassium carbonate (4.49 g) was added to a solution of trifluoromethanesulfonamide (4.66 g) and 2-bromopropiophenone (5.33 g) in N, N-dimethylformamide (40 ml). The reaction mixture was stirred at room temperature for 8 hours, water (80 ml) and ethyl acetate (80 ml) were added, the organic layer was separated, and the organic layer was washed with water. After drying the organic layer with DDL ₄ , the organic solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to purify 1,1,1-trifluoro-N- (1-oxo-1-phenylpropane-). 2-Il) Methanesulfonamide was obtained at 3.34 g (melting point 88-89 ° C.).

1-2: Synthesis of 1,1,1-trifluoro-N- (1-hydrazilidene-1-phenylpropan-2-yl) methanesulfonamide (Compound No .: B-1)
Hydrazine monohydrate in an ethanol (80 ml) solution of 1,1,1-trifluoro-N- (1-oxo-1-phenylpropan-2-yl) methanesulfonamide (C-1) (11.05 g) (10 ml) and 2.4N hydrochloric acid (1 ml) were added, and the ^{mixture was stirred at 80 o} C for 3 hours. After distilling off ethanol from the reaction solution, water (80 ml) and ethyl acetate (60 ml) were added to separate the organic layer, and then the organic layer was further washed with water. After drying the organic layer with DDL ₄ , the organic solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to purify 1,1,1-trifluoro-N- (1-hydrazilidene-1-phenylpropane-). 2-Il) Methanesulfonamide was obtained in 8.3 g (oil).

1-3: Synthesis of 1,1,1-trifluoro-N- [1- (2-formylhydrazilidene) -1-phenylpropan-2-yl] -methanesulfonamide (compound number: A-1) 1,1,1-Trifluoro-N- (1-hydrazilidene-1-phenylpropan-2-yl) methanesulfonamide (2.00 g) synthesized in 1-2 was dissolved in ethyl formate (22 ml) and formic acid. (0.56 g) was added, and the reaction solution was refluxed for 2 hours. The organic solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to purify 1,1,1-trifluoro-N- (1- (2-formylhydrazilidene) -1-phenylpropan-2-yl. )-Methanesulfonamide was obtained at 1.80 g (melting point 130-132 ° C.).

1-4: 1,1,1-Trifluoro-N- [1- (2-formyl-2-methylhydrazilidene) -1-phenylpropan-2-yl] -Synthesis of N-methylmethanesulfonamide ( Compound number: A-4)
1,1,1-Trifluoro-N- (1- (2-formylhydrazilidene) -1-phenylpropan-2-yl) -methanesulfonamide (0.65 g) synthesized in 1-3 and methyl iodide Potassium carbonate (0.55 g) was added to a solution of N, N-dimethylformamide (6 ml) with (0.51 g). The reaction mixture was stirred at room temperature for 4 hours, water and ethyl acetate were added, the organic layer was separated, and the organic layer was washed with water. After drying the organic layer with DDL ₄ , the organic solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to purify 1,1,1-trifluoro-N- [1- (2-formyl-2-). Methylhydrazilidene) -1-phenylpropan-2-yl] -N-methylmethanesulfonamide was obtained at 0.31 g (melting point 76-78 ° C).

Example 2
2-1: 1,1,1-Trifluoro-N- [1- (2-formylhydrazilidene) -1-phenylpropan-2-yl] -N-methylmethanesulfonamide (Compound No .: A-2) ) Synthesis of 1,1,1-trifluoro-N- [1- (2-formylhydrazilidene) -1-phenylpropan-2-yl] -methanesulfonamide (0.80 g) synthesized in 1-3. , N, N-Dimethylformamide (6 ml) was dissolved, methyl iodide (0.85 g) and sodium hydrogen carbonate (0.59 g) were added, and the reaction solution was stirred at room temperature for 8 hours. Ethyl acetate and water were added to the reaction solution, the layers were separated, and the organic layer was washed with water. After drying the organic layer with DDL ₄ , the organic solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to purify 1,1,1-trifluoro-N- [1- (2-formylhydrazilidene). -1-Phenylpropan-2-yl] -N-methylmethanesulfonamide was obtained at 0.72 g (melting point 96-98 ° C.).

Example 3
3-1: 1,1,1-Trifluoro-N- [1- (2-formyl-2-ethylhydrazilidene) -1-phenylpropan-2-yl] -N-methylmethanesulfonamide (compound number) : Synthesis of A-28) 1,1,1-Trifluoro-N- [1- (2-formylhydrazilidene) -1-phenylpropan-2-yl] -N-methylmethane synthesized in 2-1 Sulfonamide (0.19 g) was dissolved in N, N-dimethylformamide (2 ml), ethyl iodide (0.16 g) and potassium carbonate (0.1 g) were added, and the reaction solution was stirred at room temperature for 6 hours. Ethyl acetate and water were added to the reaction solution, the layers were separated, and the organic layer was washed with water. After drying the organic layer with DDL ₄ , the organic solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to purify 1,1,1-trifluoro-N- [1- (2-formyl-2-). Ethylhydrazilidene) -1-phenylpropan-2-yl] -N-methylmethanesulfonamide was obtained in 0.17 g (oil).

Example 4
4-1: Synthesis of N, N-dimethyl-N'-[1-phenyl-2- (trifluoromethylsulfoneamide) propyridene] formhydrazoneamide (compound number: A-172) Synthesized in 1-2 1, 1,1-Trifluoro-N- (1-hydrazilidene-1-phenylpropan-2-yl) methanesulfone amide (0.45 g) was dissolved in toluene (4 ml), and N, N-dimethylformamide dimethyl acetal (0.5 ml) was dissolved. ) Was added, and the reaction solution was refluxed for 3 hours. The organic solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 0.27 g of N, N-dimethyl-N'-[1-phenyl-2- (trifluoromethylsulfonamide) propyridene] form hydrazone amide. Obtained at (melting point 85-87 ° C).

^{The 1} H-NMR data of the compounds produced in the same manner as in the above Examples are shown in Tables 4 to 6 below. In Tables 4 to 6 below, the compound numbers correspond to those shown in Tables 1 to 3, respectively.

The pharmaceutical product containing the compound of the present invention will be specifically described below with reference to the pharmaceutical product examples, but the compound of the present invention, the auxiliary component, the amount of the additive thereof, etc. are not limited to the following pharmaceutical product examples. In addition, in the pharmaceutical product example, all parts are represented by mass parts.

Formulation Example 1 Emulsion The compound of the present invention (10 parts), N-methyl-2-pyrrolidone (reagent) (10 parts), xylene (reagent) (70 parts), and Solpol 3005X (nonionic surfactant and anionic). A mixture with a surfactant, Toho Chemical Industry Co., Ltd. (10 parts) was uniformly mixed and dissolved to obtain an emulsion.

Formulation Example 2 Hydrate Compound of the present invention (20 parts), Toxil GU-N (white carbon, Oriental Silicon Corporation) (20 parts), Solpol 5096 (polyoxyethylene styrylphenyl ether sulfate, Toho Chemical Industry Co., Ltd.) ( 10 parts) and SS clay (clay, Showa KDE Co., Ltd.) (50 parts) were mixed and then crushed using a crusher to obtain a wettable powder.

Formulation Example 3 Water Solvent The compound of the present invention (5 parts), Lunox P-65L (sodium alkylbenzene sulfonate, Toho Chemical Industry Co., Ltd.) (3 parts), and sodium hydrogen carbonate (reagent) (92 parts) are uniformly mixed. After that, it was crushed using a crusher to obtain a water solvent.

Formulation Example 4 Flowable agent The compound of the present invention (20 parts), Solpol 7948 (polyoxyalkylene tristyrylphenyl ether sodium sulfate, Toho Chemical Industry Co., Ltd.) (5 parts), propylene glycol (reagent) (10 parts), and water. (40 parts) was mixed in advance and wet-ground with a bead mill to obtain a slurry. Next, KELZAN (xanthan gum, Sansho Co., Ltd.) (0.2 parts) was well mixed and dispersed in water (24.8 parts) to prepare a gel-like product, which was sufficiently mixed with the crushed slurry to prepare a flowable agent. Obtained.

Formulation Example 5 EW-1
The compound of the present invention (20 parts) and New Calgen D-230 (polyoxyethylene castor oil, Takemoto Oil & Fat Co., Ltd.) (15 parts) were mixed and homogenized, and then water (59.8 parts) was stirred. Was gradually added to obtain a dispersion. KELZAN (xanthan gum, Sansho Co., Ltd.) (0.2 part) dispersed in propylene glycol (reagent) (5.0 parts) was added to obtain an emulsion preparation.

Formulation Example 6 EW-2
The compound of the present invention (10 parts) was dissolved in xylene (10 parts) and mixed with Leodor 430V (polyoxyethylene sorbitol tetraoleate, Kao Corporation) (24 parts) to obtain a dispersion. KELZAN (xanthan gum, Sansho Co., Ltd.) (0.2 parts) in which this dispersion and water (50.8 parts) were dispersed in a homogenizer and dispersed in propylene glycol (reagent) (5.0 parts) was used. The mixture was added to obtain an emulsion preparation.

Formulation Example 7 Microemulsion The compound of the present invention (10 parts), xylene (reagent) (20 parts), Nucalgen D-230 (polyoxyethylene castor oil, Takemoto Oil & Fat Co., Ltd.) (20 parts), Airroll CT-1L (Dioctyl) Sodium sulfosuccinate, Toho Chemical Industry Co., Ltd. (2.0 parts), and water (48 parts) were uniformly mixed to obtain a microemulsion.

Formulation Example 8 Liquid agent The compound of the present invention (20 parts), Н-methyl-2-pyrrolidone (reagent) (70 parts), and Neucalgen D-230 (polyoxyethylene castor oil, Takemoto Oil & Fat Co., Ltd.) (10 parts). The mixture was uniformly mixed and dissolved to obtain a liquid agent.

Formulation Example 9 Granule-1
The compound of the present invention (5 parts), Airroll CT-1L (sodium dioctylsulfosuccinate, Toho Chemical Industry Co., Ltd.) (2 parts), Bentonite Sado (bentonite, Kunimine Industry Co., Ltd.) (30 parts), and NK-300 (parts). Clay, Showa KDE Co., Ltd. (63 parts) was uniformly mixed, water was added, and the mixture was well kneaded, then extruded and granulated, and dried and sized to obtain granules.

Formulation Example 10 Granules-2
The compound (5 parts) of the present invention was dissolved in methanol (reagent), adsorbed on Ishikawa Light No. 2 (95 parts) using a rolling granulator, and dried to obtain granules.

Formulation Example 11 Fine Granules-1
The compound (2 parts) of the present invention was dissolved in methanol (reagent), adsorbed on Ishikawa Light No. 4 (98 parts) using a rolling granulator, and dried to obtain a fine granule.

Pharmaceutical example 12 Fine granules-2
After mixing the compound of the present invention (5 parts) and Tokseal GU-N (5 parts), the mixture was pulverized using a fine pulverizer and uniformly mixed with Iide silica sand (quartz sand, JFE Mineral Co., Ltd.) (80 parts). This mixture was further mixed with a diluted aqueous solution of Toxanone GR-31A (polycarboxylic acid type surfactant, Sanyo Chemical Industries, Ltd.) (10 parts) while spraying to obtain a granular composition. The granular composition was dried to obtain a fine granule.

Formulation Example 13 Powder agent After uniformly mixing the compound of the present invention (5 parts), Tokseal GU-N (5 parts) and Omori fine powder clay (Clay, Omori Sangyo Co., Ltd.) (90 parts), using a crusher. It was pulverized to obtain a powder.

Pharmaceutical Example 14 DL powder The compound of the present invention (5 parts), propylene glycol (0.5 parts) and DL clay (94.5 parts) were uniformly mixed and then pulverized using a pulverizer to obtain a powder.

Formulation Example 15 Seed-coated powder The compound of the present invention (10 parts), Poval PVA-117 (polyvinyl alcohol, Kuraray Trading Co., Ltd.) (1 part) and Omori fine powder clay (89 parts) are uniformly mixed and pulverized. Was pulverized using the above to obtain a powder. Pre-moistened seeds and this powder were mixed and air-dried to obtain coated seeds.

Formulation Example 16 Seed-coated flowable agent The compound of the present invention (10 parts), Solpol 7948 (5 parts), propylene glycol (reagent) (10 parts), and water (40 parts) were mixed in advance and wet-ground with a bead mill. did. Next, KELZAN (xanthan gum, Sansho Co., Ltd.) (0.2 parts) and water (29.8 parts) are well mixed and dispersed, and AMECOAT HCA / 83 (acrylic acid polymer, SOLVAY) (5 parts) is mixed. The gel-like product was prepared. The pulverized slurry and the prepared gel were sufficiently mixed to obtain a flowable agent. The flowable agent and seeds were mixed and air-dried to obtain coated seeds.

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

Comparative Agent A (No. 6 described in Patent Document 3)

Test Example 1: Effect test on the root-knot nematode (Meloidogyne incognita (Kofoid et White) Chitwood) 200 ml of the test soil adjusted to 200 nematodes / 20 g of soil was placed in a styrol cup (9 cm in diameter and 6.5 cm in height). After 50 ml of an aqueous diluted solution (100 ppm) of the emulsion prepared according to Pharmaceutical Example 1 was irrigated, tomatoes were sown (13 grains / pot). After sowing, it was grown in a greenhouse. On the 14th day of sowing, the degree of root hump of each strain was investigated in 5 stages based on the following evaluation criteria, and the Nekobu index and the control value were calculated based on the following formula.

Degree of root hump (evaluation standard): 0 (no root hump), 1 (1-2 root humps), 2 (3 or more root humps), 3 (large root hump or connected root hump) Yes. Less than 50% of all roots) 4 (More than 50% of all roots have root humps)

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

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

As a result, compound numbers A-1, A-2, A-4, A-6, A-8, A-14, A-15, A-25, A-26, A-28, A-34, A -35, A-37, A-38, A-40, A-41, A-42, A-43, A-44, A-46, A-47, A-48, A-50, A-51 , A-52, A-53, A-55, A-57, A-59, A-60, A-61, A-65, A-67, A-69, A-75, A-76, A -77, A-78, A-80, A-81, A-84, A-85, A-86, A-93, A-94, A-96, A-97, A-98, A-99 , A-100, A-101, A-102, A-103, A-104, A-105, A-106, A-107, A-108, A-109, A-115, A-116, A -118, A-120, A-127, A-128, A-130, A-131, A-132, A-134, A-136, A-138, A-148, A-150, A-151 , A-152, A-154, A-167, A-168, A-170, A-172, A-173, A-183, A-184, A-185, A-187, A-188, A -189, A-190, A-191, A-192, A-193, A-194, A-195, A-196, A-197, A-198, A-199, A-200, A-202 , A-207, A-208, A-209, A-210, A-212, A-214, and B-29 of the present invention showed a control value of 80% or more. On the other hand, Comparative Agent A had a control value of 0%.

Test Example 2: Insecticidal effect test on cucumber cotton aphid (Aphis gosiipii Glover) by spraying Leaf pieces infested with 50 to 80 adult aphid larvae were inoculated into the leaves of pot-planted cucumber seedlings raised for 2 weeks after sowing. .. The aqueous diluted solution (500 ppm) of the emulsion prepared according to Pharmaceutical Example 1 was sprayed on the leaf stem of the aphid-infested cucumber seedling on the day after inoculation using an air brush. On the 7th day after the treatment, the number of parasitic aphids was investigated, and the control rate was calculated according to the following formula. The test was carried out by using one seedling in each ward.

Control rate (%) = (1-A / B x D / C) x 100

A: Number of aphid adult larvae before spraying in the untreated plot per seedling B: Number of aphid adult larvae before spraying in the treated plot per seedling C: Number of aphid adult larvae 7 days after spraying in the untreated plot per seedling D: Per seedling Number of adult aphid larvae 7 days after spraying the treatment area

As a result, the compounds of the present invention of Compound Nos. A-44, A-53, A-57, A-60, A-97, A-168, and A-208 showed a control rate of 90% or more. On the other hand, Comparative Agent A had a control rate of 0%.

Test Example 3: Insecticidal effect test on cucumber cotton aphid (Aphis gosiipii Glover) by irrigation treatment Leaf pieces infested with 50 to 80 adult aphid larvae were inoculated into the leaves of pot-planted cucumber seedlings raised for 2 weeks after sowing. .. A water-diluted solution (500 ppm) of the emulsion prepared according to Pharmaceutical Example 1 was irrigated on the root of a cucumber seedling infested with aphids on the day after inoculation. On the 7th day after the treatment, the number of parasitic aphids was investigated, and the control rate was calculated according to the following formula. The test was carried out by using one seedling in each ward.

Control rate (%) = (1-A / B x D / C) x 100

A: Number of aphid adult larvae before spraying in the untreated plot per seedling B: Number of aphid adult larvae before spraying in the treated plot per seedling C: Number of aphid adult larvae 7 days after spraying in the untreated plot per seedling D: Per seedling Number of adult aphid larvae 7 days after spraying the treatment area

As a result, compound numbers A-1, A-28, A-38, A-40, A-44, A-57, A-61, A-98, A-148, A-150, A-191, and The compound of the present invention of C-1 showed a control rate of 80% or more. On the other hand, Comparative Agent A had a control rate of 0%.

Test Example 4: Insect killing test against Thrips palmi Karny A water-diluted solution (500 ppm) of the emulsion prepared according to Formulation Example 1 is aired on the leaves of pot-planted cucumber seedlings raised for 2 weeks after sowing. A sufficient amount was sprayed using a brush. After air-drying the chemical solution, inoculate a 7 mm x 7 mm filter paper inoculated with about 50 thrips eggs so that the eggs touch the cucumber cotyledons, and put them in a dish case (65 mm x 65 mm, height 95 mm) (1). Strain / case), kept in a constant temperature room at 26 ° C. Six days after treatment, the number of surviving insects was investigated in the following grades. The test was carried out by using one seedling in each ward.

Control rate 100% = 0 heads Control rate 90% = 1-2 heads Control rate 50% = 3 heads ~ half of untreated plots Control rate 0% = half of untreated plots ~ same number as untreated plots

As a result, the compounds of the present invention of Compound Nos. A-2, A-44, A-51, A-96, and A-104 showed a control rate of 90% or more. On the other hand, Comparative Agent A had a control rate of 0%.

Test Example 5: Imago test against Tetranychus urticae Koch A 430 ml capacity polyethylene cup containing water was covered with a lid having a hole (diameter about 5 mm) in the center. A circular filter paper having a diameter of 6.5 cm was cut with a width of about 5 mm, and a strip-shaped portion hanging downward was inserted through a 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 the primary leaves of the common bean were placed on cotton wool in a state where the water in the cup was constantly replenished, and 10 adult female spider mites were placed on the leaf discs. Inoculated. This cup was placed in an acrylic cylinder having a height of 50 cm and a diameter of 10 cm, and an aqueous diluted solution (500 ppm) of the emulsion prepared according to Pharmaceutical Example 1 was sprayed at 2.0 ml per cup using an airbrush. After spraying, it was kept in a constant temperature room at 25 ° C. Four days after the treatment, the life and death of adults and anguish were investigated under binocular, and the insecticidal rate (%) was determined with the anguish as dead. The test was carried out by using 1 cup in each section.

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

As a result, compound numbers A-2, A-9, A-28, A-34, A-41, A-43, A-44, A-55, A-57, A-59, A-60, A -61, A-65, A-67, A-77, A-78, A-81, A-82, A-83, A-97, A-98, A-99, A-102, A-103 , A-104, A-148, A-152, A-154, A-168, A-173, A-184, A-189, A-191, A-192, A-193, A-194, A -196, A-198, A-199, A-201, and A-210 of the present invention showed 100% insecticidal rate. On the other hand, Comparative Agent A had an insecticidal rate of 0%.

Test Example 6: Density suppression test against Tetranychus urticae Koch A 430 ml capacity polyethylene cup containing water was covered with a lid having a hole (diameter about 5 mm) in the center. A circular filter paper having a diameter of 6.5 cm was cut with a width of about 5 mm, and a strip-shaped portion hanging downward was inserted through a 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 the primary leaves of the common bean were placed on cotton wool in a state where the water in the cup was constantly replenished, and 10 adult female spider mites were placed on the leaf discs. Inoculated. This cup was placed in an acrylic cylinder having a height of 50 cm and a diameter of 10 cm, and an aqueous diluted solution (500 ppm) of the emulsion prepared according to Pharmaceutical Example 1 was sprayed at 2.0 ml per cup using an airbrush. After spraying, it was kept in a constant temperature room at 25 ° C. Next-generation density suppression effect on eggs laid by adults 7 days after treatment was 100 (density suppression rate: 100%), 95 (same: 99-95%), 80 (same: 94-80%), 50 (same::). It was evaluated in 5 stages of 79-50%) and 0 (same: less than 50%), and the next-generation density suppression rate was calculated by the following formula based on the results. The test was carried out by using 1 cup in each section.

Next-generation density suppression rate = (A x 100 + B x 95 + C x 80 + D x 50) / (A + B + C + D + E)
A: 100 discs, B: 95 discs, C: 80 discs, D: 50 discs, E: 0 discs

As a result, compound numbers A-2, A-9, A-40, A-42, A-44, A-51, A-52, A-53, A-55, A-57, A-59, A -60, A-61, A-65, A-67, A-68, A-76, A-77, A-78, A-81, A-82, A-83, A-90, A-91 , A-96, A-97, A-98, A-99, A-100, A-101, A-102, A-103, A-104, A-107, A-120, A-148, A -167, A-168, A-170, A-172, A-173, A-184, A-189, A-190, A-191, A-192, A-193, A-194, A-195 , A-196, A-197, A-198, and A-210 of the present invention showed a density suppression rate of 100%. On the other hand, Comparative Agent A had a density suppression rate of 0%.

Claims

The following formula (1),

[During the ceremony,
R 1 is a hydrogen atom, C 1-6 alkyl group, C 2-6 alkenyl group, C 2-6 alkynyl group, C 1-6 haloalkyl group, C 1-6 alkoxy C 1-6 alkyl group, C 1- 6 alkoxycarbonyl C 1-6 alkyl group, cyano C 1-6 alkyl group or optionally substituted benzyl group, indicating
R 2 indicates a formyl group, or R 1 and R 2 together,

May form,
R 3 indicates a C 1-6 alkyl group,
R 4 is a hydrogen atom, C 1-6 alkyl group, C 1-6 haloalkyl group, C 3-6 cycloalkyl group, C 2-6 alkenyl group, C 2-6 alkynyl group, C 2-6 haloalkyl group. , C 2-6 haloalkynyl group, C 1-6 alkoxy C 1-6 alkyl group, C 1-6 alkoxycarbonyl C 1-6 alkyl group or optionally substituted benzyl group.
R 5 represents a C 1-6 haloalkyl group
R 6 indicates OR 7 or NR 8 R 9
R 7 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 hydroxy C. 1-6 alkyl group, C 1-6 alkoxy C 1-6 alkyl group, C 3-6 cycloalkyl group, C 3-6 cycloalkyl C 1-6 alkyl group or optionally substituted benzyl group.
R 8 represents a hydrogen atom or a C 1-6 alkyl group.
R 9 is a hydrogen atom, C 1-6 alkyl group, C 1-6 alkoxy group, C 1-6 haloalkyl group, C 2-6 alkenyl group, C 2-6 haloalkenyl group, C 2-6 alkynyl group, C 2-6 haloalkynyl group, hydroxy C 1-6 alkyl group, C 1-6 alkoxy C 1-6 alkyl group, C 3-6 cycloalkyl group, C 3-6 cycloalkyl C 1-6 alkyl group or substituted Indicates a benzyl group which may be, or R 8 and R 9 are attached to each other and together with the nitrogen atom to which R 8 and R 9 are attached, 4 to 7 saturated or unsaturated. It may form a member ring,
X may be the same or different, hydrogen atom, C 1-6 alkyl group, C 1-6 haloalkyl group, C 3-6 cycloalkyl group, C 2-6 alkoxy group, C 2-6 alkynyl group, C. 2-6 haloalkoxy group, C 2-6 haloalkynyl group, C 1-6 alkoxy group, C 1-6 haloalkoxy group, C 1-6 alkylthio group, C 3-6 halocycloalkyl group, C 1-6 If it represents an alkoxycarbonyl group, a formyl group, a halogen atom, a cyano group or a nitro group, or if two Xs are present in place of a hydrogen atom on two adjacent carbon atoms, the two above. X may be combined with the carbon atoms to which each is bonded to form a saturated or unsaturated 5- or 6-membered ring, and
n indicates an integer from 1 to 5. ]
A hydrazone derivative, or a salt thereof, characterized by being represented by.
R 1 indicates a hydrogen atom or C 1-6 alkyl group, R 2 indicates a formyl group, R 3 indicates a methyl group, an ethyl group or an isopropyl group, and R 4 indicates a hydrogen atom or C 1-. The hydrazone derivative according to claim 1, or a salt thereof, which exhibits a 6-alkyl group.
The following formula (2),

[During the ceremony,
R 1 is C 1-6 alkyl group, C 1-6 alkenyl group, C 1-6 alkynyl group, C 1-6 haloalkyl group, C 1-6 alkoxy C 1-6 alkyl group, C 1-6 alkoxycarbonyl. Indicates a C 1-6 alkyl group, a cyano C 1-6 alkyl group or an optionally substituted benzyl group.
R 3 indicates a C 1-6 alkyl group,
R 4 is a hydrogen atom, C 1-6 alkyl group, C 1-6 haloalkyl group, C 3-6 cycloalkyl group, C 2-6 alkenyl group, C 2-6 alkynyl group, C 2-6 haloalkyl group. , C 2-6 haloalkynyl group, C 1-6 alkoxy C 1-6 alkyl group, C 1-6 alkoxycarbonyl C 1-6 alkyl group or optionally substituted benzyl group.
R 5 represents a C 1-6 haloalkyl group
X may be the same or different, hydrogen atom, C 1-6 alkyl group, C 1-6 haloalkyl group, C 3-6 cycloalkyl group, C 2-6 alkoxy group, C 2-6 alkynyl group, C. 2-6 haloalkoxy group, C 2-6 haloalkynyl group, C 1-6 alkoxy group, C 1-6 haloalkoxy group, C 1-6 alkylthio group, C 3-6 halocycloalkyl group, C 1-6 If it represents an alkoxycarbonyl group, a formyl group, a halogen atom, a cyano group or a nitro group, or if two Xs are present in place of a hydrogen atom on two adjacent carbon atoms, the two Xs mentioned above. May form a saturated or unsaturated 5- or 6-membered ring, together with the carbon atoms to which each is bonded, and
n indicates an integer from 1 to 5. ]
It is a method for producing a hydrazone derivative represented by.
The following formula (3),

[In the equation, R 3 , R 4 , R 5 , X, and n are as defined in the above equation (2). ]
Hydrazone derivative represented by and the following formula (4),

[In the formula, R 1 indicates a substituent defined by the above formula (2), and L indicates a leaving group. ]
A production method comprising reacting with an alkylating agent represented by.
The following formula (2),

[During the ceremony,
R 1 is a hydrogen atom, C 1-6 alkyl group, C 1-6 alkenyl group, C 1-6 alkynyl group, C 1-6 haloalkyl group, C 1-6 alkoxy C 1-6 alkyl group, C 1- 6 alkoxycarbonyl C 1-6 alkyl group, cyano C 1-6 alkyl group or optionally substituted benzyl group, indicating
R 3 indicates a C 1-6 alkyl group,
R 4 is C 1-6 alkyl group, C 1-6 haloalkyl group, C 3-6 cycloalkyl group, C 2-6 alkenyl group, C 2-6 alkynyl group, C 2-6 haloalkenyl group, C 2 -6 Haloalkynyl group, C 1-6 alkoxy C 1-6 alkyl group, C 1-6 alkoxycarbonyl C 1-6 alkyl group or optionally substituted benzyl group.
R 5 represents a C 1-6 haloalkyl group
X may be the same or different, hydrogen atom, C 1-6 alkyl group, C 1-6 haloalkyl group, C 3-6 cycloalkyl group, C 2-6 alkoxy group, C 2-6 alkynyl group, C. 2-6 haloalkoxy group, C 2-6 haloalkynyl group, C 1-6 alkoxy group, C 1-6 haloalkoxy group, C 1-6 alkylthio group, C 3-6 halocycloalkyl group, C 1-6 If it represents an alkoxycarbonyl group, a formyl group, a halogen atom, a cyano group or a nitro group, or if two Xs are present in place of a hydrogen atom on two adjacent carbon atoms, the two above. X may be combined with the carbon atoms to which each is bonded to form a saturated or unsaturated 5- or 6-membered ring, and
n indicates an integer from 1 to 5. ]
It is a method for producing a hydrazone derivative represented by.
Equation (5),

[In the equation, R 1 , R 3 , R 5, X, and n are as defined in the above equation (2). ]
Hydrazone derivative represented by and the following formula (6),
L-R 4 (6)
[In the formula, R 4 indicates a substituent defined by the above formula (2), and L indicates a leaving group. ]
A production method comprising reacting with an alkylating agent represented by.
The following formula (2),

[During the ceremony,
R 1 is a hydrogen atom, C 1-6 alkyl group, C 1-6 alkenyl group, C 1-6 alkynyl group, C 1-6 haloalkyl group, C 1-6 alkoxy C 1-6 alkyl group, C 1- 6 alkoxycarbonyl C 1-6 alkyl group, cyano C 1-6 alkyl group or optionally substituted benzyl group, indicating
R 3 indicates a C 1-6 alkyl group,
R 4 is a hydrogen atom, C 1-6 alkyl group, C 1-6 haloalkyl group, C 3-6 cycloalkyl group, C 2-6 alkenyl group, C 2-6 alkynyl group, C 2-6 haloalkyl group. , C 2-6 haloalkynyl group, C 1-6 alkoxy C 1-6 alkyl group, C 1-6 alkoxycarbonyl C 1-6 alkyl group or optionally substituted benzyl group.
R 5 represents a C 1-6 haloalkyl group
X may be the same or different, hydrogen atom, C 1-6 alkyl group, C 1-6 haloalkyl group, C 3-6 cycloalkyl group, C 2-6 alkoxy group, C 2-6 alkynyl group, C. 2-6 haloalkoxy group, C 2-6 haloalkynyl group, C 1-6 alkoxy group, C 1-6 haloalkoxy group, C 1-6 alkylthio group, C 3-6 halocycloalkyl group, C 1-6 If it represents an alkoxycarbonyl group, a formyl group, a halogen atom, a cyano group or a nitro group, or if two Xs are present in place of a hydrogen atom on two adjacent carbon atoms, the two above. X may be combined with the carbon atoms to which each is bonded to form a saturated or unsaturated 5- or 6-membered ring, and
n indicates an integer from 1 to 5. ]
It is a method for producing a hydrazone derivative represented by.
Equation (7),

[In the equation, R 1 , R 3 , R 4 , R 5, X, and n are as defined in the above equation (2). ]
Hydrazone derivative represented by, formic acid and / or the following formula (8),
HCOOR 10 (8)
[In the formula, R 10 represents a C 1-6 alkyl group. ]
A production method comprising reacting with a formate ester represented by.
The following formula (9),

[During the ceremony,
R 3 indicates a C 1-6 alkyl group,
R 4 is a hydrogen atom, C 1-6 alkyl group, C 1-6 haloalkyl group, C 3-6 cycloalkyl group, C 2-6 alkenyl group, C 2-6 alkynyl group, C 2-6 haloalkyl group. , C 2-6 haloalkynyl group, C 1-6 alkoxy C 1-6 alkyl group, C 1-6 alkoxycarbonyl C 1-6 alkyl group or optionally substituted benzyl group.
R 5 represents a C 1-6 haloalkyl group
R 6 indicates OR 7 or NR 8 R 9
R 7 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 hydroxy C. 1-6 alkyl group, C 1-6 alkoxy C 1-6 alkyl group, C 3-6 cycloalkyl group, C 3-6 cycloalkyl C 1-6 alkyl group or optionally substituted benzyl group.
R 8 represents a hydrogen atom or a C 1-6 alkyl group.
R 9 is a hydrogen atom, C 1-6 alkyl group, C 1-6 alkoxy group, C 1-6 haloalkyl group, C 2-6 alkenyl group, C 2-6 haloalkenyl group, C 2-6 alkynyl group, C 2-6 haloalkynyl group, hydroxy C 1-6 alkyl group, C 1-6 alkoxy C 1-6 alkyl group, C 3-6 cycloalkyl group, C 3-6 cycloalkyl C 1-6 alkyl group or substituted Indicates a benzyl group which may be, or R 8 and R 9 are attached to each other and together with the nitrogen atom to which R 8 and R 9 are attached, 4 to 7 saturated or unsaturated. It may form a member ring,
X may be the same or different, hydrogen atom, C 1-6 alkyl group, C 1-6 haloalkyl group, C 3-6 cycloalkyl group, C 2-6 alkoxy group, C 2-6 alkynyl group, C. 2-6 haloalkoxy group, C 2-6 haloalkynyl group, C 1-6 alkoxy group, C 1-6 haloalkoxy group, C 1-6 alkylthio group, C 3-6 halocycloalkyl group, C 1-6 If it represents an alkoxycarbonyl group, a formyl group, a halogen atom, a cyano group or a nitro group, or if two Xs are present in place of a hydrogen atom on two adjacent carbon atoms, the two above. X may be combined with the carbon atoms to which each is bonded to form a saturated or unsaturated 5- or 6-membered ring, and
n indicates an integer from 1 to 5. ]
It is a method for producing a hydrazone derivative represented by.
Equation (7),

[In the equation, R 1 indicates a hydrogen atom, and R 3 , R 4 , R 5 , X, and n are as defined in the above equation (9). ]
Hydrazone derivative represented by and the following formula (10),

[In the formula, R 6 is as defined by the above formula (9), and R 10 represents a C 1-6 alkyl group, which may be the same or different. ]
A production method comprising reacting with an acetal derivative represented by.
Equation (11),

[During the ceremony,
R 3 indicates a C 1-6 alkyl group,
R 4 is a hydrogen atom, C 1-6 alkyl group, C 1-6 haloalkyl group, C 3-6 cycloalkyl group, C 2-6 alkenyl group, C 2-6 alkynyl group, C 2-6 haloalkyl group. , C 2-6 haloalkynyl group, C 1-6 alkoxy C 1-6 alkyl group, C 1-6 alkoxycarbonyl C 1-6 alkyl group or optionally substituted benzyl group.
R 5 represents a C 1-6 haloalkyl group
R 8 represents a hydrogen atom or a C 1-6 alkyl group.
R 9 is a hydrogen atom, C 1-6 alkyl group, C 1-6 alkoxy group, C 1-6 haloalkyl group, C 2-6 alkenyl group, C 2-6 haloalkenyl group, C 2-6 alkynyl group, C 2-6 haloalkynyl group, hydroxy C 1-6 alkyl group, C 1-6 alkoxy C 1-6 alkyl group, C 3-6 cycloalkyl group, C 3-6 cycloalkyl C 1-6 alkyl group or substituted Indicates a benzyl group which may be, or R 8 and R 9 are attached to each other and together with the nitrogen atom to which R 8 and R 9 are attached, 4 to 7 saturated or unsaturated. It may form a member ring,
X may be the same or different, hydrogen atom, C 1-6 alkyl group, C 1-6 haloalkyl group, C 3-6 cycloalkyl group, C 2-6 alkoxy group, C 2-6 alkynyl group, C. 2-6 haloalkoxy group, C 2-6 haloalkynyl group, C 1-6 alkoxy group, C 1-6 haloalkoxy group, C 1-6 alkylthio group, C 3-6 halocycloalkyl group, C 1-6 If it represents an alkoxycarbonyl group, a formyl group, a halogen atom, a cyano group or a nitro group, or if two Xs are present in place of a hydrogen atom on two adjacent carbon atoms, the two above. X may be combined with the carbon atoms to which each is bonded to form a saturated or unsaturated 5- or 6-membered ring, and
n indicates an integer from 1 to 5. ]
It is a method for producing a hydrazone derivative represented by.
Equation (12),

[In the formula, R 3 , R 4 , R 5 , X, and n are as defined in the above formula (11), and R 10 indicates a C 1-6 alkyl group. ]
Hydrazone derivative represented by and the following formula (13),

[In the formula, R 8 and R 9 are as defined in the formula (11). ]
A production method comprising reacting with an amine derivative represented by.
A farming and horticultural drug containing the hydrazone derivative according to claim 1 or 2 or a salt thereof.
A nematode control agent for agriculture and horticulture containing the hydrazone derivative according to claim 1 or 2 or a salt thereof.
A farming and horticultural pest control agent containing the hydrazone derivative according to claim 1 or 2 or a salt thereof.
Harmful plants, including the step of treating pests and / or their habitats and / or seeds and / or plant propagation materials targeted by the pests with the agricultural and horticultural agents according to claim 9. How to control living things.
A plant pest comprising a step of treating a place where a useful crop is to be grown, a place where the crop is grown, or a growing crop with the agricultural and horticultural agent according to claim 9. How to prevent.
A method for preparing a pesticide composition, which comprises a step of mixing the agricultural and horticultural agent according to claim 9 with a bulking agent and / or a surfactant.
Equation (7),

[During the ceremony,
R 1 is a hydrogen atom, C 1-6 alkyl group, C 2-6 alkenyl group, C 2-6 alkynyl group, C 1-6 haloalkyl group, C 1-6 alkoxy C 1-6 alkyl group, C 1- 6 alkoxycarbonyl C 1-6 alkyl group, cyano C 1-6 alkyl group or optionally substituted benzyl group, indicating
R 3 indicates a C 1-6 alkyl group,
R 4 is a hydrogen atom, C 1-6 alkyl group, C 1-6 haloalkyl group, C 3-6 cycloalkyl group, C 2-6 alkenyl group, C 2-6 alkynyl group, C 2-6 haloalkyl group. , C 2-6 haloalkynyl group, C 1-6 alkoxy C 1-6 alkyl group, C 1-6 alkoxycarbonyl C 1-6 alkyl group or optionally substituted benzyl group.
R 5 represents a C 1-6 haloalkyl group
X may be the same or different, hydrogen atom, C 1-6 alkyl group, C 1-6 haloalkyl group, C 3-6 cycloalkyl group, C 2-6 alkoxy group, C 2-6 alkynyl group, C. 2-6 haloalkoxy group, C 2-6 haloalkynyl group, C 1-6 alkoxy group, C 1-6 haloalkoxy group, C 1-6 alkylthio group, C 3-6 halocycloalkyl group, C 1-6 If it represents an alkoxycarbonyl group, a formyl group, a halogen atom, a cyano group or a nitro group, or if two Xs are present in place of a hydrogen atom on two adjacent carbon atoms, the two above. X may be combined with the carbon atoms to which each is bonded to form a saturated or unsaturated 5- or 6-membered ring, and
n indicates an integer from 1 to 5. ]
A hydrazone derivative, or a salt thereof, characterized by being represented by.
Equation (16),

[During the ceremony,
R 3 indicates a C 1-6 alkyl group,
R 4 is a hydrogen atom, C 1-6 alkyl group, C 1-6 haloalkyl group, C 3-6 cycloalkyl group, C 2-6 alkenyl group, C 2-6 alkynyl group, C 2-6 haloalkyl group. , C 2-6 haloalkynyl group, C 1-6 alkoxy C 1-6 alkyl group, C 1-6 alkoxycarbonyl C 1-6 alkyl group or optionally substituted benzyl group.
R 5 represents a C 1-6 haloalkyl group
X may be the same or different, hydrogen atom, C 1-6 alkyl group, C 1-6 haloalkyl group, C 3-6 cycloalkyl group, C 2-6 alkoxy group, C 2-6 alkynyl group, C. 2-6 haloalkoxy group, C 2-6 haloalkynyl group, C 1-6 alkoxy group, C 1-6 haloalkoxy group, C 1-6 alkylthio group, C 3-6 halocycloalkyl group, C 1-6 If it represents an alkoxycarbonyl group, a formyl group, a halogen atom, a cyano group or a nitro group, or if two Xs are present in place of a hydrogen atom on two adjacent carbon atoms, the two above. X may be combined with the carbon atoms to which each is bonded to form a saturated or unsaturated 5- or 6-membered ring, and
n indicates an integer from 1 to 5. ]
A ketone derivative, or a salt thereof, characterized by being represented by.
Equation (7),

[During the ceremony,
R 1 is a hydrogen atom, C 1-6 alkyl group, C 2-6 alkenyl group, C 2-6 alkynyl group, C 1-6 haloalkyl group, C 1-6 alkoxy C 1-6 alkyl group, C 1- 6 alkoxycarbonyl C 1-6 alkyl group, cyano C 1-6 alkyl group or optionally substituted benzyl group, indicating
R 3 indicates a C 1-6 alkyl group,
R 4 is a hydrogen atom, C 1-6 alkyl group, C 1-6 haloalkyl group, C 3-6 cycloalkyl group, C 2-6 alkenyl group, C 2-6 alkynyl group, C 2-6 haloalkyl group. , C 2-6 haloalkynyl group, C 1-6 alkoxy C 1-6 alkyl group, C 1-6 alkoxycarbonyl C 1-6 alkyl group or optionally substituted benzyl group.
R 5 represents a C 1-6 haloalkyl group
X may be the same or different, hydrogen atom, C 1-6 alkyl group, C 1-6 haloalkyl group, C 3-6 cycloalkyl group, C 2-6 alkoxy group, C 2-6 alkynyl group, C. 2-6 haloalkoxy group, C 2-6 haloalkynyl group, C 1-6 alkoxy group, C 1-6 haloalkoxy group, C 1-6 alkylthio group, C 3-6 halocycloalkyl group, C 1-6 If it represents an alkoxycarbonyl group, a formyl group, a halogen atom, a cyano group or a nitro group, or if two Xs are present in place of a hydrogen atom on two adjacent carbon atoms, the two above. X may be combined with the carbon atoms to which each is bonded to form a saturated or unsaturated 5- or 6-membered ring, and
n indicates an integer from 1 to 5. ]
It is a method for producing a hydrazone derivative represented by.
Equation (16),

[In the equation, R 3 , R 4 , R 5 , X and n are as defined in equation (7). ]
A method for producing a hydrazone derivative, which comprises reacting the ketone derivative represented by (1 ) with NH 2 NHR 1 (R 1 is as defined by the formula (7)).
Equation (16),

[During the ceremony,
R 3 indicates a C 1-6 alkyl group,
R 4 is a hydrogen atom, C 1-6 alkyl group, C 1-6 haloalkyl group, C 3-6 cycloalkyl group, C 2-6 alkenyl group, C 2-6 alkynyl group, C 2-6 haloalkyl group. , C 2-6 haloalkynyl group, C 1-6 alkoxy C 1-6 alkyl group, C 1-6 alkoxycarbonyl C 1-6 alkyl group or optionally substituted benzyl group.
R 5 represents a C 1-6 haloalkyl group
X may be the same or different, hydrogen atom, C 1-6 alkyl group, C 1-6 haloalkyl group, C 3-6 cycloalkyl group, C 2-6 alkoxy group, C 2-6 alkynyl group, C. 2-6 haloalkoxy group, C 2-6 haloalkynyl group, C 1-6 alkoxy group, C 1-6 haloalkoxy group, C 1-6 alkylthio group, C 3-6 halocycloalkyl group, C 1-6 If it represents an alkoxycarbonyl group, a formyl group, a halogen atom, a cyano group or a nitro group, or if two Xs are present in place of a hydrogen atom on two adjacent carbon atoms, the two above. X may be combined with the carbon atoms to which each is bonded to form a saturated or unsaturated 5- or 6-membered ring, and
n indicates an integer from 1 to 5. ]
It is a method for producing a ketone derivative shown by
Equation (14),

[In the formula, R 3 , X and n are as defined in the formula (16), and Hal indicates a halogen atom. ]
The ketone derivative indicated by
Equation (15),

[In the formula, R 4 and R 5 are as defined in the formula (16). ]
A method for producing a ketone derivative, which comprises reacting with a compound represented by.