JP2022065219A - Novel hydrazone derivative and agricultural and horticultural agent using the same as active ingredient - Google Patents

Abstract

To provide a novel compound that can be used as an agricultural and horticultural agent.SOLUTION: The present invention discloses a hydrazone derivative represented by the following formula (1) or a salt thereof [where R1 is H, an alkyl group or the like, R2 is a formyl group or the like, R3 is an alkyl group or a phenyl group, X is H, an alkyl group or the like, n is an integer of 1 to 5, and Y1 to Y4 each denote a nitrogen atom or an optionally substituted alkyl group].SELECTED DRAWING: None

Description

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, a nematode control agent or a disease control agent, and a method for 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, Patent Document 1 discloses a semicarbazone compound, but does not disclose a hydrazone compound 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 4). However, all of these compounds disclosed in Patent Documents 2 to 4 have different chemical structures from the compounds of the present invention.

Japanese Unexamined Patent Publication No. 8-073436 International Publication No. 01/36381 Japanese Patent Application Laid-Open No. 2002-155044 International Publication No. 93/19045

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

[式中、R₁は、水素原子又はＣ_1-6アルキル基を示し、
R₂は、ホルミル基を示し、或いは
R₁とR₂は一緒になり、

を形成してもよく、
R₄は、OR₅又はNR₆R₇を示し、
R₅は、Ｃ_1-6アルキル基、Ｃ_1-6ハロアルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6ハロアルケニル基、Ｃ_2-6アルキニル基、Ｃ_2-6ハロアルキニル基、ヒドロキシＣ_1-6アルキル基、Ｃ_1-6アルコキシＣ_1-6アルキル基、Ｃ_3-6シクロアルキル基、Ｃ_3-6シクロアルキルＣ_1-6アルキル基又はベンジル基を示し、
R₆は、水素原子又はＣ_1-6アルキル基を示し、
R₇は、水素原子、Ｃ_1-6アルキル基、Ｃ_1-6ハロアルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6ハロアルケニル基、Ｃ_2-6アルキニル基、Ｃ_2-6ハロアルキニル基、ヒドロキシＣ_1-6アルキル基、Ｃ_1-6アルコキシＣ_1-6アルキル基、Ｃ_3-6シクロアルキル基、Ｃ_3-6シクロアルキルＣ_1-6アルキル基又はベンジル基を示し、或いは
R₆とR₇は、互いに結合して、R₆とR₇が結合している窒素原子と一緒に飽和又は不飽和の4～7員環を形成してもよく、
R₃は、Ｃ_1-6アルキル基又はフェニル基を示し、
Xは同一又は異なってもよく、水素原子、Ｃ_1-6アルキル基、Ｃ_1-6ハロアルキル基、Ｃ_3-6シクロアルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6アルキニル基、Ｃ_2-6ハロアルケニル基、Ｃ_2-6ハロアルキニル基、Ｃ_1-6アルコキシ基、Ｃ_1-6ハロアルコキシ基、Ｃ_1-6アルキルチオ基、Ｃ_3-6ハロシクロアルキル基、Ｃ_1-6アルキコキシカルボニル基、ホルミル基、ハロゲン原子、シアノ基又はニトロ基を示すか、或いは、２個のXが隣接する２個の炭素原子上の水素原子と置換して存在する場合、前記２個のXはそれぞれが結合している炭素原子と一緒になって飽和又は不飽和の５又は６員環を形成してもよく、
nは、1から5の整数を示し、
Y₁、Y₂、Y₃及びY₄は、それぞれ独立に、窒素原子又はCR基を示し、
Rは、それぞれ独立に、水素原子、Ｃ_1-6アルキル基、Ｃ_1-6ハロアルキル基、Ｃ_1-6アルキルチオ基、Ｃ_1-6アルキルスルフィニル基、Ｃ_1-6アルキルスルホニル基、Ｃ_1-6アルコキシ基、Ｃ_1-6アルキコキシカルボニル基、ハロゲン原子、シアノ基又はニトロ基を示す。]
で表されるヒドラゾン誘導体又はその塩に関し、更に、該化合物を有効成分とする農園芸用薬剤、特に農園芸用害虫防除剤、線虫防除剤又は病害防除剤、及びその使用方法並びに該化合物等の製造方法に関するものである。 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 that it is useful as a control agent, a nematode control agent or a disease control agent.
That is, the present invention has the following equation (1).

[In the formula, R ₁ represents a hydrogen atom or a C _1-6 alkyl group.
R ₂ indicates a formyl group, or
R ₁ and R ₂ come together,

May form,
R ₄ indicates OR ₅ or NR ₆ R ₇
R ₅ is C _1-6 alkyl 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 Alkyl C _1-6 Alkyl Group, C _3-6 Cycloalkyl Group, C _3-6 Cycloalkyl C _1-6 Alkyl Group or benzyl Group.
R ₆ represents a hydrogen atom or a C _1-6 alkyl group.
R ₇ is a hydrogen atom, C _1-6 alkyl 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 ₆ and R ₇ may be bonded to each other to form a saturated or unsaturated 4- to 7-membered ring with the nitrogen atom to which R ₆ and R ₇ are bonded.
R ₃ indicates a C _1-6 alkyl group or phenyl 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 alkoxy group If a coxycarbonyl group, formyl group, halogen atom, cyano group or nitro group is indicated, or if two Xs are present in place of a hydrogen atom on two adjacent carbon atoms, the above two X may be combined with the carbon atoms to which each is bonded to form a saturated or unsaturated 5- or 6-membered ring.
n indicates an integer from 1 to 5
Y ₁ , Y ₂ , Y ₃ and Y ₄ independently represent a nitrogen atom or CR group, respectively.
R is independently a hydrogen atom, a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _1-6 alkylthio group, a C _1-6 alkyl sulfinyl group, a C _1-6 alkyl sulfonyl group, and a C _1- . ₆ Shows an alkoxy group, a C _1-6 alkyloxycarbonyl group, a halogen atom, a cyano group or a nitro group. ]
Regarding the hydrazone derivative represented by (1) or a salt thereof, further, an agricultural and horticultural agent containing the compound as an active ingredient, particularly an agricultural and horticultural pest control agent, a nematode control agent or a disease control agent, a method of using the compound, and the like. It is related to the manufacturing method of.

The compound of the present invention exerts an excellent effect as an agricultural and horticultural agent, particularly as an agricultural and horticultural pest control agent, a nematode control agent or a disease 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 "halogen atom" means a chlorine atom, a bromine atom, an iodine atom or a fluorine atom, and the "C _1-6 alkyl group" means, for example, a methyl group, an ethyl group, an n-propyl group or i. -Propyl group, n-butyl group, i-butyl group, s-butyl group, t-butyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, n-hexyl group, isohexyl group, etc. It represents an alkyl group having 1 to 6 carbon atoms in a chain or branched chain, and is a linear or branched chain substituted with one or more halogen atoms which may be the same or different from "C _1-6 haloalkyl". "C _3-6 cycloalkyl" refers to cyclic cycloalkyl groups having 3 to 6 carbon atoms such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. show.

In the compounds described herein, R ₆ and R ₇ may bond to each other and combine with the nitrogen atoms bonded to R ₆ and R ₇ to form a 4- to 7-membered ring, even if the ring is saturated. It may be 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, when two Xs are present in place of hydrogen atoms on two adjacent carbon atoms of the phenyl ring, these Xs are bonded to each other and the respective Xs are bonded. It can form a saturated or unsaturated 5- or 6-membered ring together with the carbon atoms, but for example, it is condensed with a phenyl ring to form an indan ring, a tetrahydronaphthalene ring, and a naphthalene ring, 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 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.

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- Number of carbon atoms 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 2 to 6 linear or branched alkenyl groups.
Examples of the C _2-6 haloalkenyl group include 1-fluorovinyl group, 2-fluorovinyl group, 2,2-difluorovinyl group, 3-chloro-2-propenyl group 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, Examples thereof include a linear or branched alkenyl group having 2 to 6 carbon atoms substituted with 1 to 9 halogen atoms having at least one double bond at an arbitrary position such as a 6-fluoro-2-hexenyl group. Be done.

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 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 a linear or branched alkynyl group 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 a fluoromethoxy group, a dichloromethoxy group, a trichloromethoxy group, a difluoromethoxy group, a trifluoromethoxy group, a chlorodifluoromethoxy group, a bromodifluoromethoxy group, a dichlorofluoromethoxy group and 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 a linear or branched alkoxy group having 1 to 6 carbon atoms substituted with a halogen atom.

Examples of the C _1-6 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 a halocycloalkyl group having 1 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.

Examples of the C _1-6 alkoxycarbonyl group include groups such as methoxycarbonyl, ethoxycarbonyl, n-propylcarbonyl, n-butylcarbonyl, n-pentylcarbonyl, n-hexylcarbonyl and i-propylcarbonyl group.
C _1-6 alkoxy Examples of the C _1-6 alkyl group include a methoxymethyl group, an ethoxymethyl group, a methoxyethyl group, an ethoxyethyl group, a 3-methoxypropyl group and the like.
Examples of the hydroxy C _1-6 alkyl group include a hydroxymethyl group, a 2-hydroxyethyl group, a 2-hydroxypropyl group, a 3-hydroxypropyl group, a 3-hydroxy-2,2-dimethylpropyl group and the like. Be done.

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, a linear or branched alkylthio group having 1 to 6 carbon atoms can be mentioned.
Examples of the C _1-6 alkylsulfinyl group include methylsulfinyl group, ethylsulfinyl group, n-propylsulfinyl group, isopropylsulfinyl group, cyclopropylsulfinyl group, n-butylsulfinyl group, s-butylsulfinyl group and t-butyl. Examples thereof include a linear or branched alkyl sulfinyl group having 1 to 6 carbon atoms such as a sulfinyl group, an n-pentylsulfinyl group, and an n-hexylsulfinyl group.
Examples of the C _1-6 alkyl sulfonyl group include a methyl sulfonyl group, an ethyl sulfonyl group, an n-propyl sulfonyl group, an isopropyl sulfonyl group, a cyclopropyl sulfonyl group, an n-butyl sulfonyl group, an s-butyl sulfonyl group, and t-butyl. Examples thereof include a linear or branched alkylsulfonyl group having 1 to 6 carbon atoms such as a sulfonyl group, an n-pentylsulfonyl group, and an n-hexylsulfonyl group.

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 oxalic acids. Organic acid salts such as 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, it is preferable that Y ₂ shows CR.
In the hydrazone derivative represented by the above formula (1) of the present invention, it is preferable that R represents a C _1-6 haloalkyl group.
In the hydrazone derivative represented by the above formula (1) of the present invention, it is preferable that R ₃ exhibits a methyl group or an ethyl group.
In the hydrazone derivative represented by the formula (1) of the present invention, it is more preferable that Y ₂ represents CR, R represents a C _1-6 haloalkyl group, and R ₃ represents a methyl group or an ethyl group.

[式中、R₃は、Ｃ_1-6アルキル基又はフェニル基を示し、
Xは同一又は異なってもよく、水素原子、Ｃ_1-6アルキル基、Ｃ_1-6ハロアルキル基、Ｃ_3-6シクロアルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6アルキニル基、Ｃ_2-6ハロアルケニル基、Ｃ_2-6ハロアルキニル基、Ｃ_1-6アルコキシ基、Ｃ_1-6ハロアルコキシ基、Ｃ_1-6アルキルチオ基、Ｃ_3-6ハロシクロアルキル基、Ｃ_1-6アルキコキシカルボニル基、ホルミル基、ハロゲン原子、シアノ基又はニトロ基を示すか、或いは、２個のXが隣接する２個の炭素原子上の水素原子と置換して存在する場合、前記２個のXはそれぞれが結合している炭素原子と一緒になって飽和又は不飽和の５又は６員環を形成してもよく、
nは、1から5の整数を示し、
Y₁、Y₂、Y₃及びY₄は、それぞれ独立に、窒素原子又はCR基を示し、
Rは、それぞれ独立に、水素原子、Ｃ_1-6アルキル基、Ｃ_1-6ハロアルキル基、Ｃ_1-6アルキルチオ基、Ｃ_1-6アルキルスルフィニル基、Ｃ_1-6アルキルスルホニル基、Ｃ_1-6アルコキシ基、Ｃ_1-6アルキコキシカルボニル基、ハロゲン原子、シアノ基又はニトロ基を示し、
Halはハロゲン原子を示す。]
反応式１に示す方法においては、前記式（３）で表されるケトン誘導体は、前記式（１２）で表されるα－ハロゲンケトン化合物と前記式（１３）のアゾール化合物とを、塩基の存在下又は不存在下に、不活性溶媒中で反応させることにより製造することができる。 Hereinafter, representative production of the novel hydrazone derivative represented by the formula (1) of the present invention, the hydrazone derivative represented by the formula (2) and the ketone derivative represented by the formula (3), which are intermediates thereof. Although the method is shown, the method for producing the above compound is not limited to these in the present invention.
Reaction equation 1

[In the formula, R ₃ represents a C _1-6 alkyl group or phenyl 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 alkoxy group If a coxycarbonyl group, a formyl group, a halogen atom, a cyano group or a nitro group is indicated, or if two Xs are present in place of a hydrogen atom on two adjacent carbon atoms, the above two X may be combined with the carbon atoms to which each is bonded to form a saturated or unsaturated 5- or 6-membered ring.
n indicates an integer from 1 to 5
Y ₁ , Y ₂ , Y ₃ and Y ₄ independently represent a nitrogen atom or CR group, respectively.
R is independently a hydrogen atom, a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _1-6 alkylthio group, a C _1-6 alkyl sulfinyl group, a C _1-6 alkyl sulfonyl group, and a C _1- . Shows ₆ alkoxy groups, C _1-6 alkyloxycarbonyl groups, halogen atoms, cyano groups or nitro groups,
Hal indicates a halogen atom. ]
In the method represented by the reaction formula 1, the ketone derivative represented by the formula (3) is a base of the α-halogen ketone compound represented by the formula (12) and the azole compound of the formula (13). It can be produced by reacting in the presence or absence of an inert solvent.

As the solvent used in the reaction between the compound of the formula (12) and the compound of the formula (13), a known solvent can be widely used as long as it is 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-. 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 (12) and the compound of the formula (13), 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 ketone compound represented by the formula (12).

The ratio of the α-halogen ketone compound represented by the formula (12) to the azole compound represented by the formula (13) is 1 to 1.2 mol of the compound (13) with respect to the compound (12). It is more preferable to do.
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.

［式中、R₁は、水素原子又はＣ_1-6アルキル基を示し、X, Y₁, Y₂, Y₃, Y₄, R₃及びnは前記式（３）で定義した通りである。］
反応式２に示す方法においては、前記式（２）で表されるヒドラゾン誘導体は、前記式（３）で表されるケトン化合物と前記式（１１）のヒドラジン化合物とを、酸の存在下又は不存在下に、不活性溶媒中で反応させることにより製造することができる。 Reaction equation 2

[In the formula, R ₁ represents a hydrogen atom or a C _1-6 alkyl group, and X, Y ₁ , Y ₂ , Y ₃ , Y ₄ , R ₃ and n are as defined in the above formula (3). .. ]
In the method represented by the reaction formula 2, the hydrazone derivative represented by the formula (2) is a ketone compound represented by the formula (3) and a hydrazine compound represented by the formula (11) in the presence of an acid or. It can be produced by reacting in the absence of an inert solvent.

As the solvent used in the reaction between the ketone derivative of the formula (3) and the hydrazine compound of the formula (11), 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 (3) and the compound of the formula (11), 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 can 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 (3).

The ratio of the ketone derivative of the formula (3) to the hydrazine compound represented by the formula (11) can be appropriately selected from a wide range, but the latter is 1 to 10 with respect to 1 mol of the former. It is preferable to use more than mol, 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.

［式中、R₈はＣ_1-6アルキル基を示し、X, Y₁, Y₂, Y₃, Y₄, R₁, R₃及びnは前記式（２）及び（３）で定義した通りである。］
反応式３に示す方法においては、前記式（４）で表されるヒドラゾン誘導体は、前記式（２）で表されるヒドラゾン誘導体とギ酸及び／又は前記式（５）で表されるギ酸誘導体とのホルミル化反応により製造することができる。 Reaction equation 3

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

As the solvent used in the formylation reaction of the hydrazone compound represented by the formula (2), 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 -Amid-based solvents such as dimethylformamide, nitrile-based solvents such as acetonitrile and propionitrile, aprotonic polar solvents such as N-methylpyrrolidone and N, N'-dimethylimidazolinone, and acetic acid can be mentioned. One of these solvents can be used alone, or two or more of these solvents can be mixed and used as required.
Examples of the formylation agent used in the formylation reaction of the hydrazone compound represented by the formula (2) 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 (2).
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.

［式中、R₈はＣ_1-6アルキル基を示し、X, Y₁, Y₂, Y₃, Y₄, R₁, R₃及びnは前記で定義した通りである。］
この反応式４に関し、その具体的な態様としては、以下に記載の反応式５及び７で示されるものが挙げられる。 Reaction equation 4

[In the formula, R ₈ represents a C _1-6 alkyl group, and X, Y ₁ , Y ₂ , Y ₃ , Y ₄ , R ₁ , R ₃ and n are as defined above. ]
Specific embodiments of the reaction formula 4 include those represented by the reaction formulas 5 and 7 described below.

［式中、R₁は水素原子、R₈はＣ_1-6アルキル基を示し、X, Y₁, Y₂, Y₃, Y₄, R₃及びnは前記で定義した通りである。］
反応式５に示す方法においては、前記式（９）で表されるヒドラゾン誘導体は、前記式（２）で表されるヒドラゾン誘導体とオルトギ酸エステル（１４）との反応により製造することができる。 Reaction equation 5

[In the formula, R ₁ represents a hydrogen atom, R ₈ represents a C _1-6 alkyl group, and X, Y ₁ , Y ₂ , Y ₃ , Y ₄ , R ₃ and n are as defined above. ]
In the method represented by the reaction formula 5, the hydrazone derivative represented by the formula (9) can be produced by reacting the hydrazone derivative represented by the formula (2) with the orthoformate ester (14).

As the solvent used in the reaction between the hydrazone compound represented by the formula (2) and the orthoformate ester represented by the formula (14), a known solvent is widely used as long as it is 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 -Amid-based solvents such as dimethylformamide, nitrile-based solvents such as acetonitrile and propionitrile, aprotonic polar solvents such as N-methylpyrrolidone and N, N'-dimethylimidazolinone, and acetic acid can be mentioned. One of these solvents can be used alone, or two or more of these solvents can be mixed and used as required.
Examples of the orthoformate ester (14) used in the iminization reaction of the hydrazone compound represented by the formula (2) include methyl orthoformate, ethyl orthoformate, propyl orthoformate, butyl orthoformate and the like.
Such an orthoformate ester (14) can be used in an amount usually 1 to 20 equivalents, preferably 2 to 10 equivalents, relative to the hydrazone derivative represented by the formula (2).
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.

［式中、R₆は水素原子又はＣ_1-6アルキル基を示し、R₇は、水素原子、Ｃ_1-6アルキル基、Ｃ_1-6ハロアルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6ハロアルケニル基、Ｃ_2-6アルキニル基、Ｃ_2-6ハロアルキニル基、ヒドロキシＣ_1-6アルキル基、Ｃ_1-6アルコキシＣ_1-6アルキル基、Ｃ_3-6シクロアルキル基、Ｃ_3-6シクロアルキルＣ_1-6アルキル基又はベンジル基を示し、或いは、R₆とR₇は、互いに結合して、R₆とR₇が結合している窒素原子と一緒に飽和又は不飽和の4～7員環を形成してもよい。X, Y₁, Y₂, Y₃, Y₄, R₃, R₈及びnは前記で定義した通りである。］
反応式６に示す方法においては、前記式（８）で表されるヒドラゾン誘導体は、前記式（９）で表されるヒドラゾン誘導体と前記式（１０）で表されるアミン誘導体との反応により製造することができる。 Reaction equation 6

[In the formula, R ₆ indicates a hydrogen atom or a C _1-6 alkyl group, and R ₇ is a hydrogen atom, a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _2-6 alkyl group, and a 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 benzyl group, or R ₆ and R ₇ are bonded to each other and saturated or unsaturated with the nitrogen atom to which R ₆ and R ₇ are bonded. A 4- to 7-membered ring may be formed. X, Y ₁ , Y ₂ , Y ₃ , Y ₄ , R ₃ , R ₈ and n are as defined above. ]
In the method represented by the reaction formula 6, the hydrazone derivative represented by the formula (8) is produced by reacting the hydrazone derivative represented by the formula (9) with the amine derivative represented by the formula (10). can do.

As the solvent used in the amination reaction of the hydrazone compound represented by the formula (9), 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 -Amid-based solvents such as dimethylformamide, nitrile-based solvents such as acetonitrile and propionitrile, aprotonic polar solvents such as N-methylpyrrolidone and N, N'-dimethylimidazolinone, and acetic acid can be mentioned. One of these solvents can be used alone, or two or more of these solvents can be mixed and used as required.
The amine derivative (10) 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 (9).
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.

［式中、R₁は水素原子を示し、X, Y₁, Y₂, Y₃, Y₄, R₃、R₆、R₇、R₈及びnは前記で定義した通りである。］
反応式７に示す方法においては、前記式（８）で表されるヒドラゾン誘導体は、前記式（２）で表されるヒドラゾン誘導体とアセタール誘導体（１５）との反応により製造することができる。 Reaction equation 7

[In the equation, R ₁ represents a hydrogen atom, and X, Y ₁ , Y ₂ , Y ₃ , Y ₄ , R ₃ , R ₆ , R ₇ , R ₈ and n are as defined above. ]
In the method represented by the reaction formula 7, the hydrazone derivative represented by the formula (8) can be produced by reacting the hydrazone derivative represented by the formula (2) with the acetal derivative (15).

As the solvent used in the reaction between the hydrazone compound represented by the formula (2) and the acetal derivative represented by the formula (15), known solvents are widely used as long as they are inert to the reaction. be able to. 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 -Amid-based solvents such as dimethylformamide, nitrile-based solvents such as acetonitrile and propionitrile, aprotonic polar solvents such as N-methylpyrrolidone and N, N'-dimethylimidazolinone, and acetic acid can be mentioned. One of these solvents can be used alone, or two or more of these solvents can be mixed and used as required.
Examples of the acetal derivative (15) used in the iminization reaction of the hydrazone compound represented by the formula (2) include N, N-dimethylformamide dimethylacetal and the like.
The acetal derivative (15) 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 (2).
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.

Typical compounds of the hydrazone derivative represented by the formula (1) are shown in Table 1, representative compounds of the hydrazone derivative represented by the formula (2) are shown in Table 2, and representative compounds of the hydrazone derivative represented by the formula (2) are shown in the above formula (3). Table 3 exemplifies typical compounds of the ketone derivatives to be used, but the present invention is not limited thereto.
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. * 1 indicates that -CH = CH-CH = CH- is bonded to the 3rd and 4th positions of the phenyl group. * 2 indicates that -CH = CH-CH = CH- is bonded to the 2nd and 3rd positions of the phenyl group.
Also, A-56 and A-57, A-123 and A-124, A-125 and A-126, A-127 and A-128, A-129 and A-130, A-131 and A-132, A-133 and A-134, A-135 and A-136, A-137 and A-138, A-139 and A-140, A-141 and A-142, A-143 and A-144, A- 145 and A-146, A-147 and A-148, A-149 and A-150, A-151 and A-152, A-153 and A-154, A-155 and A-156, A-157 and A-158, A-159 and A-160, A-161 and A-162, A-163 and A-164, A-166 and A-167, A-169 and A-170 are isomers, respectively. It is in.

General formula (1)

General formula (2)

General formula (3)

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, an edible crop (wheat such as rice, barley, wheat, rye, oat, corn, horse bell 薯, sweet potato, satoimo, soybean, small bean, sora bean, Beans such as red beans, green beans, peanuts, etc.), vegetables (cabbage, white vegetables, radish, buds, broccoli, potash flowers, komatsuna, etc. , Nasu, tomatoes, peppers, peppers, okura, spinach, lettuce, bricks, carrots, gobos, garlic, onions, onions, etc.), mushrooms (shitake, mushrooms, etc.), fruit trees / fruits (apples, citrus fruits, etc.) , Pears, grapes, peaches, plums, cherry peaches, peaches, chestnuts, almonds, bananas, strawberries, etc.), fragrances and other viewing crops (lavender, rosemary, thyme, parsley, pepper, ginger, etc.), special crops (tobacco, 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.), Grasses (Koryo turf, bentgrass, etc.), forest trees (beans, beans, pine trees, hiba, cedars, foxes, etc.) and ornamental plants (crops, roses, carnations, orchids, herbs, flowers, ginkgo, cherry blossoms, etc.) Varieties, garden trees such as Aoki, etc.) Damage to legumes, soft animals, nematodes, and fungi such as fungi, deformed fungi, bacterial phylum, radiation fungi, and harmful organisms such as bacteria. Can also be used to control. Specific pests include the following.

Lepidoptera of the phylum Arthropod, for example, Helicoverpa armigera, Heliothis spp., Agrotis segetum, Autographa nigrisigna, Trichoplusia ni ), Yotoga (Mamestra brassicae), Shiroichimojiyoto (Spodoptera exigua), Hasmonyoto (Spodoptera litura), etc. honmai), Midarekakumonhamaki (Archips fuscocupreanus), Chahamaki (Homona magnanima), Chanohosoga (Caloptilia theivora), Nashihimeshinkui (Grapholita molesta), Eumeta minuscula, etc. malinella), Lyonetia clerkella, etc., Phyllocnistis citrella, etc., Phyllocnistis citrella, etc., Phyllonorycter ringoniella, etc. , Stahmopoda masinissa, etc., Pectinophora gossypiella, etc., Carposina niponensis, Carposina niponensis, Cossus jezoensis, etc. , Iraga family Iraga (Monema flavecens), Hirohelia oila (Parasa lepida), Himekuroiraga (Scopelodes con) Tracus, etc., Crambi suppressalis, Scirpophaga incertulas, Cnaphalocrocis medinalis, Helulla undalis, Conogethes punctiferlis, Wataheli phandica Pyraloid moth (Parapediasia teterrella), Pyraloid moth (Locastra muscosalis), Pyraloid moth (Parnara guttata), Pyraloid moth (Papilio xuthus), etc. Pyraloid moth (Lampides boeticus), Pyraloid moth (Ascotis selenaria), Crambid moth (Agrius convolvuli), Pyraloid moth (Phalera flavescens), etc. Neustrium testaceum), Saturnia japonica, etc., Chadokuga (Euproctis pseudoconspersa), Orgyia thyellina, Akamondokuga (Telochurus recens approximans), etc. , American white-spotted moth (Hyphantria cunea), adult worms, larvae and eggs such as 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 Epilachna vigintioctopunctata, etc. Aulacophora femoralis), root worm species (Diabrotica spp.), Weevil leaf beetle (Phyllotreta striolata), leaf beetle (Cassida nebulosa), leaf beetle (Phaedon brassicae), leaf beetle (Oulema oryzae), Mexican leaf beetle (Eulema oryzae), Mexican beetle (Epilema oryzae) ), Etc., Chrysomelidae weevil (Rhynchites heros), Chrysomelidae weevil (Cylas formicarius), etc. Adults, larvae and eggs such as grandis), leaf beetle (Sphenophrus venatus vestitus), and Epuraea domina of the family Coleoptera;

Hemiptera stink bugs (Heteroptera), such as 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 (Togo hemipterus) , Stink bugs (Cletus punctiger), etc., Stink bugs (Leptocorisa chinensis), stink bugs (Dysdeercus cingulatus), etc. Etc., stink bugs (Apolygus spinolai), stink bugs (Stenotus rubrovittalus), stink bugs (Trigonotylus coelestialium), stink bugs (Megacopta punctatissimum), stink bugs (Megacopta punctatissimum), etc.

Homoptera of the order Hemiptera, for example, Platypleura kaempferi of the semi-family, Arboridia apicalis of the aphidaceae, Empoasca onukii, Empoasca onukii, , Taiwan Tsumaguro Yokobai (Nephotettix virescens), etc., Himetobiunka (Laodelphax striatellus), Tobiirounka (Nilaparvata lugens), Segatella furcifera, etc. Various biotypes of aphids (Diaphorina citri), aphids (Aleurocanthus spiniferus), silver leaf aphids (Bemisia argentifolii), tobacco aphids (Bemisia tabaci), aphids (Dialeurodes citri), etc. , Viteus vitifolii, Aphis citricola, Aphis craccivora, Aphis gossypii, Aphis gossypii, Aula corthum solani ), Comic aphid (Toxoptera aurantii), Mikan black aphid (Toxoptera citricidus), Niwatokohigenaga aphid (Aulacorthum magnoliae), Nasia bramushi (Schizaphis piricola), Nasimidrio aphid (Nippolachnus piri), Nippolachnus piri Momokofuki aphid (Hyalopterus pruni), Kikugikugi aphid (Pleotrichophorus chrysanthemi), scale insect (Macrosiphoniella sanborni), scale insect (Megoura crassicauda), scale insect (Sitobion ibarae), tulip scale insect (Macrosiphum euphorbiae) cer. Scale insects (Pseudococcus comstocki), scale insects (Phenacoccus viburnae), Fujikona scale insects (Phenacoccus kraunhiae), scale insects (Ceroplastes ceriferus), scale insects (Ceroplastes ceriferus), scale insects (Ceroplastes ceriferus) Adults, larvae and eggs of scale insects (Aonidiella aurantii), pear scale insects (Comstockaspis perniciosa), scale insects (Pseudaula caspis pentagoa), scale insects (Unaspis yanonensis);

Thrips (Thysanoptera), for example, Thrips palmi (Scirtothrips dorsalis), Thrips palmi, Thrips tabaci, Thrips tabaci, Thrips tabaci, Thrips setossa 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 (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 phylum arthropod Collembola, such as Collembola, for example, Sminthurus viridis, and Onychiurus matsumotoi, which is a rootfeeding springtail;
Adults, larvae and eggs of the phylum Malacostracans (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 mollusc phylum gastropods, such as Pomacea canaliculata of the family Tanishimodoki, Plumonata, such as the African snail (Achatina fulica) of the family Slug, of the family Slug. Slugs (Meghimatium bilineatum), Keelback slugs (Milax gagates), Keelback slugs (Lehmannina valentiana), Giant African snails (Acusta despecta sieboldiana), etc.
Tylenchida, Tylenchida, Tylenchida, Ditylenchus destructor, Tylenchorhynchus claytoni, etc. ), Pratylenchus coffeae, etc., Helicotylenchus dihystera, etc., Heterodera rostochiensis, Globodera rostochiensis, etc. Nematodes (Criconema jaejuense), etc., Strawberry nematodes of the Anguina family (Nothotylenchus acris), etc.
Uropygial glandular order, such as Ohari nematode (Xiphinema sp.) Of the Longidrus family, Yumihari nematode (Trichodorus sp.) Of the 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 plantarii, etc. Erysiphe graminis, Fusarium head blight (Gibberella zeae), Fusarium head blight (Puccinia striiformis, P. graminis, P. recondita, P. hordei), Snow rot (Typhula sp., Micronectriella nivalis) , Ustilago tritici, U. nuda, Tilletia caries, Pseudocercosporella herpotrichoides, Rhynchosporium secalis, Septoria tritici, Leptosphaeria nodorum ), Pyrenophora teres, Helminthosporium zonatum Ikata, Pseudomonas syringae pv. Japonica, etc .; citrus black spot disease (Diaporthe citri), scab (Elsinoe fawcetti), fruit rot Diseases (Penicillium digitatum, P. italicum), brown rot (Phytophthora citrophthora ,, P. nicotianae), scab (Phyllosticta citricarpa), etc .; (Podosphaera leucotricha), spot foliar disease (Alternaria mali), scab (Venturia inaequa) lis), black spot disease (My cospherella pomi), charcoal hum acutatum, botryosphaeria berengeriana, gymnosporangium yamadae, monilinia fructicola, etc .; no scab (Venturia nashicola,) 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 grape 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, Didymella bryoniae Fusarium oxysporum, Pseudoperonospora cubensis, Phytophthora sp., Pythium sp., Etc.; Pseudomonas syringae pv. Lochrymans, Gymnosporangium (Pseudomona s viridiflava), 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. Acidovorax avenae pv. Citrulli, etc .; 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), Spot bacterial disease (Xanthomonas campestris pv. Vitians) Negi rust (Puccinia allii), etc .; glycines), black spot disease (Diapor the phaseolorum var. Sojae), etc .; Colletotrichum lindem thianum, etc .; Brown spot disease (Cercospora arachidicola), etc .; Powdery mildew (Erysiphe pisi), etc .; Diseases (Sphaerotheca humuli), etc .; Tea net blast (Exobasidium reticulatum), White spot disease (Elsinoe leucospila), Red burning disease (Pseudomonas syringae pv. Theae), Powdery mildew (Xanthomonas campestris pv. Theicola), etc.; (Alternaria longipes), powdery mildew (Erysiphe cichoracearum), charcoal disease (Colletotrichum tabacum), sticky disease (Peronospora tabacina), plague (Phytophthora nicotianae), wilt (Ralstonia solanacearum), cavity disease (Pectobacterium carotovorum subsp. carotovorum, etc .; Cercospora beticola, Aphanomyces cochliodes, etc .; Rose scab (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa), etc .; -indici), powdery mildew (Puccinia horiana), powdery mildew (Agrobacterium tumefaciens), etc .; Snow rot of turf (Pythium iwayamai, Tyohula incarnate, Fusarium nivale, Sclerotinia borealis), powdery mildew (Erysiphe graminis), fariling disease (Lycoperdon perlatum, Lepista subnudo, Marasmius oreades), pseudo-leaf rot (C) 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), Anobiidae (Callosobruchus chinensis), Anobiidae (Bruchus pisorum), Anobiidae (Bruchus pisorum), Anobiidae (Bruchus pisorum) Maize weevil (Tribolium castaneum), Hirata maize weevil (Tribolium confusum), etc. (Stegobium paniceum), etc., Anobiidae (Attagenus unicolor japonicus), Anobiidae (Anthrenus verbasci), Harajiro cutaneous beetle (Dermestes maculatus), etc. Adults, larvae and eggs of the Anobiidae, Lyctus brunneus, such as the Anobiidae (Dinoderus minutus) and the Maize weevil (Rhizopertha dominica);

The order of the butterfly, for example, the tinea translucens (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 Psocoptera, such as Liposcelis bostrychophilus, for example, Liposcelis bostrychophilus, for example, Liposcelis bostrychophilus:
Adults, larvae and eggs of the order Cockroach, such as the German cockroach (Blattella germanica), the German cockroach (Periplaneta fuliginosa), and the Japanese cockroach (Periplaneta japonica);
Hymenoptera, for example, adults, larvae and eggs such as Monomorium pharaoni, Monomorium nipponense, etc. of the ant family;

Adults, larvae and eggs of the order Thysanura, such as Ctenolepisma villosa and Lepisma saccharina of the family Lepismatidae;
Adults, larvae and eggs of the order Flies, such as Drosophila melangogaster, 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.

Lepidoptera of the phylum Insectidae, such as Calliteara argentata, Euproctis pseudoconspersa, Orygia recens approximans, Euproctis subflava, Lymantria dispar, etc. Lackey moth (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, and Microleon longipalpis;
Coleoptera, for example, Himekogane (Anomala rufocuprea), Nagachakogane (Heptophylla picea), Agrilus spinipennis, etc. Basilepta pallidula), etc., Scepticus griseus of the family Curculionidae, Shirahoshizo insidiosus, etc., Sipalinus gigas, etc. Adults, larvae and eggs such as Rhizopertha dominica of the family Curculionidae, such as aceris);

C. Adults, larvae and eggs such as ceriferus);
Adults, larvae and eggs of the order Hymenoptera, such as the Sawfly Pachynematus itoi, the Neodiprion sertifer, and the Dryocosmus kuriohilus.
Flies, for example, Crane fly (Tipula aino), Cecidomyiidae (Strobilomyia laricicola), Cecidomyiidae (Contarinia inouyei), Cecidomyiidae (Contarinia inouyei), Cecidomyiidae (Contarinia matsusintome), etc. egg;
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 and experimental animals of birds such as ducks and pigeons. 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, Westermann paragonimiasis, Japanese chicken egg fluke, etc.;
Tapeworms, such as foliate tapeworms, Moniezia expansus, Moniezia beneda, square tapeworms, stabbed tapeworms, raillietina cesticillus, etc .:
Root mastigophora of the Protozoa phylum Flagellate, eg, Histomonas et al., Protozoan flagellate, eg Leishmania, Trypanosoma, etc., Multi-flagellate, eg, Giardia, etc.
Amoeba eyes of the fleshy class, such as Entamoeba;
Piroplasma subclasses of the parasitic protozoa, such as Theilaria, Babesia, etc., Late parasitic subclasses, such as Eimeria, Plasmadium, Toxoplasma, etc.

The compound of the present invention 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, the family Ceratopogonidae (Armigeres subalbatus), the family Ceratopogonidae (Culicoides nipponensis), the family Ceratopogonidae (Chironomus yoshimatsui), the family Ceratopogonidae (Simulium nikkoense), etc. Family Aokoab (Hirosia humilis), Housefly family Fly (Musca domestica), etc., Housefly family Himei fly (Fannia canicularis), Black fly family Crokin fly (Phormia regina), 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 Periplaneta, 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 Polydesmida, such as adults, larvae and eggs such as Polydesmida (Oxidus gracilis) of the family Polydesmida;
Arthropods Crustaceans of the order, for example, adults, larvae and eggs such as 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, Staphylococcus aureus, Staphylococcus aureus, etc. Gram-positive bacteria such as aureus.

The compound of the present invention represented by the above formula (1) is a pest that damages 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 supplements conventionally used in the technical field of agricultural and horticultural chemicals can be appropriately used. Such pesticide aids can be used, for example, for the purpose of improving the effect, stabilizing, and improving the dispersibility of agricultural and horticultural chemicals.

Examples of the pesticide auxiliary agent include carriers (diluents), spreading agents, emulsifiers, wet spreading agents, dispersants, disintegrants and the like. Liquid carriers include water, aromatic hydrocarbons such as toluene and xylene, alcohols such as methanol, butanol and glycol, ketones such as acetone, amides such as dimethylformamide, sulfoxides such as 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 spreading agent; a wetting agent such as dialkylsulfosuccinate; a fixing agent such as carboxymethyl cellulose and polyvinyl alcohol; a disintegrating agent 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 form, 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.
When the target pest is mainly damaging plants in the soil, or when the drug is absorbed from the root to control the target pest, for example, the preparation is not diluted or diluted with water. A method of applying to a plant stock or a nursery for raising seedlings, a method of spraying granules on a plant stock or a nursery for raising seedlings, a powder, a wettable powder, or granule water before sowing or transplanting. Method of spraying Japanese medicine, granules, etc. and mixing with the whole soil, powder, wettable powder, granule wettable powder, granules, fine granules, etc. 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 formulations such as jumbo agents, pack agents, granules and granule wettable powders, and liquid formulations such as flowables and emulsions are usually sprayed on paddy fields in a flooded state. In addition, at the time of rice planting, an appropriate preparation can be sprayed or injected into the soil as it is or mixed with fertilizer or the like. Further, by using a chemical solution such as an emulsion or 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 a seed in a liquid state by diluting or not diluting a liquid or solid preparation to attach and permeate a drug, or 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 an adhesive carrier such as a resin or a polymer and coating 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 propagation 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 are mixed with other active compounds such as insecticides, acaricides, nematodes, bactericides, repellents or synergists. It can also be present as an agent, with the total amount of active ingredient compounds in these formulations 0.0001-95% by weight, preferably 0.005-10% by weight for oils, powders and granules, emulsions and wettable powders and sol agents. Can contain 0.01 to 50% by weight. 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 cereals, fruits, nuts, spices and 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 cereals, lepidoptera, mites and fungi. Also, when storing animal products (skin, hair, wool and feathers, etc.) and plant products (cotton, paper, etc.) in a natural or converted state, from the attack of lepidoptera, stag beetles, stains and cockroaches. It can be protected and can be protected from attacks by lepidoptera, cockroaches, flies and mites when storing foods such as meat and fish. In such situations, methods such as spraying oils, emulsions, wettable powders, powders, etc., installing resin transpiration agents, treating smoke agents and fumes, installing granules, tablets and poison bait, spraying aerosol, etc. Can be controlled with. These formulations can also be present as a mixture with other active compounds such as pesticides, acaricides, nematodes, fungicides, repellents or synergists, and are included in these formulations. Can contain 0.0001 to 95% by weight 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 a suitable 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 formulation in an amount of 0.0001 to 0.1% by weight, preferably 0.001 to 0.01% by weight. 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 controlling arthropods locally or systemically 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 thereto. It's not something.
When administered orally as medicated drinking water, the beverage is usually dissolved in a suitable non-toxic solvent or water, suspension or dispersion with a suspending agent such as bentonite or a wetting agent or other excipient. be. Beverages generally also contain an antifoaming agent. Beverage formulations generally contain 0.01-1.0% by weight, preferably 0.01-0.1% by weight, of the active ingredient compound.
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 fumigants such as, smoke agents such as fogging, treatment of ULV agents, installation of granules, tablets and poison bait, or channels such as floating powders, 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, and 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 can also exist as a mixed agent with other active compounds such as a pest control agent, a tick control agent, a nematode control agent, a disease control agent, a repellent or a synergistic agent. , The active ingredient compound is contained in these formulations in a total amount of 0.0001 to 95% by weight.

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, abdominals, and nematodes that damage plants when used in combination with a compound (insecticide) having pest control activity, tick 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.

Organic phosphorus 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 .;
Organochlorine agents such as aldrin, chlordane, DDT (p, p'-DDT), endosulfan, lindane, etc .;

Pyrethroids such as acrinathrin, allethrin, bifenthrin, cycloprothrin, cyhalothrin, cyhalothrin, cyphenothrin, cypermethrin, delta. deltamethrin, ethofenprox, fenpropathrin, fenvalerate, flucythrinate, flufenprox, fluvalinate, furamethrin, halophen Prox (halfenprox), imiprothrin (imiprothrin) permethrin (permethrin), phenothrin (phenothrin), prallethrin (prallethrin), pyrethrin (pyrethrins), resmethrin (resmethrin), silafluofen (silafluofen), tefluthrin (tefluthrin) 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.;
Insecticide derived from natural substances, such as anabasine, azadiractin, deguelin, fatty acid glyceride (decanolyoctanoylglycerol), hydroxy propyl ester, soy lecithin, 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 KUI-1821 (test name) )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 formula (1) can also exist as a mixture 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 medicine 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 (difenoconazole) 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, iminoctadine acetate, iminoctadine acetate Salt (iminoctadine acetate), iminoctadine albesilate (iminoctadine-DBS), ipconazole (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, 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) (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, amicarbazone, 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), Intomopox virus (EPV), Granulosis virus (GV), Nuclear polyhedron virus (Nuclear). Virus preparations such as polyhedrosis virus (NPV), Beauveria bassiana, Beauveria brongniartii, Monocrosporium phymatophagum, Pekiromyces fumosoroseus (Paecilomyces fumosoroseus) , Steinernema carpocapsae, Steinernema glaseri, Steinernema kushidai, Verticillium lecanii, etc. Micropesticide, Agrobacterium radiobactor, Bacillus subtilis, non-pathogenic Erwinia carotovora, non-pathogenic Fusarium oxysporum, Pseudomonas CAB-02 (Pseudomonas) CAB-02), Pseudomonas fluorescens, Talaromyces flavus, Trichoderma atroviride, Trichoderma lignorum, and other microbial pesticides used as bactericides, Zantmonas. Similar effects can be expected by using it in combination with biopesticide used as a herbicide such as campestris (Xanthomonas campestris).

Further, as biological pesticides, for example, Amblyseius californicus, Amblyseius cucumeris, Amblyseius degenerans, Aphidius colemani, Aphidius colemani, Aphidoletes aphidiza Chrysoperia carnea), Hamoglycomayu bee (Dacnusa sibirica), Isaea Himekobachi (Diglyphus isaea), Onsitsutsuyakobachi (Encarsia formosa), Sabakutsuyakobachi (Eretmocerus eremicus), Arigatashima Azamiuma (Franklinoth) Hemiptarsenus varicornis, Neochrysocharis formosa, Orius sauteri, Orius strigicollis, Predatory mite, Phytoseiulus persimilis Natural enemy creatures such as varius, codlelure, cuelure, geraniol, gyptol, liblure, looplure, methyl eugenol, orfralure, It can also be used in combination with pheromone agents such as peachflure, phycilure, pyrimalure, and turpentine.

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
Synthesis of N'-(2- (3-trifluoromethyl) -1,2,4-triazole-1-yl) -1-phenylpropyridene) form hydrazide (Compound No .: A-3)
Synthesis of 1-1: 2- (3-trifluoromethyl-1,2,4-triazole-1-yl) propiophenone (Compound No .: C-2)
Potassium carbonate (9.66 g) was added to a solution of 3-trifluoromethyl-1,2,4-triazole (7.00 g) and 2-bromopropiophenone (10.66 g) in N, N-dimethylformamide (40 ml). The reaction mixture was stirred at room temperature for 3 hours, water (60 ml) and ethyl acetate (80 ml) were added, the organic layer was separated, and 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 2- (3-trifluoromethyl-1,2,4-triazole-1-yl) propio. 11.05 g (oil) of phenone was obtained.

1-2: Synthesis of (2- (3-trifluoromethyl) -1,2,4-triazole-1-yl) -1-phenylpropyridene (compound number: B-2)
Hydrazine monohydrate (10 ml) and 2N in ethanol (80 ml) solution of 2- (3-trifluoromethyl-1,2,4-triazole-1-yl) propiophenone (C-2) (11.05 g) A hydrogen chloride ethanol solution (7 ml) was added, and the mixture was stirred at 60 ^o C for 3 hours. After distilling off ethanol from the reaction solution, water (80 ml) and ethyl acetate (60 ml) were added, the organic layer was separated, and 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 (2- (3-trifluoromethyl) -1,2,4-triazole-1-yl). ) -1-Phenylpropyridene) Hydrazide was obtained in 8.3 g (oil).

1-3: Synthesis of N'-(2- (3-trifluoromethyl) -1,2,4-triazole-1-yl) -1-phenylpropyridene) form hydrazide (compound number: A-3) 1- Hydrazide (0.50 g) synthesized in 2 (2- (3-trifluoromethyl) -1,2,4-triazole-1-yl) -1-phenylpropyridene was dissolved in ethyl formate (5 ml) and formic acid (2). 0.1 ml) was added, and the reaction solution was refluxed for 1 hour. The organic solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to form N'-(2- (3-trifluoromethyl) -1,2,4-triazole-1-yl) -1-phenylpropyridene) form. Hydrazide was obtained at 0.49 g (mp 127-129 ° C.).

Example 2
N, N-dimethyl-N'-(2- (3-trifluoromethyl) -1,2,4-triazole-1-yl) -1-phenylpropyridene) form hydrazone amide (compound number: A-4) Synthetic
(2- (3-Trifluoromethyl) -1,2,4-triazole-1-yl) -1-phenylpropyridene) Hydrazide (0.50 g) was dissolved in toluene (5 ml) and N, N-dimethylformamide dimethyl. Acetal (0.5 ml) 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 N, N-dimethyl-N'-(2- (3-trifluoromethyl) -1,2,4-triazole-1-yl)-. 1-Phenylpropyridene) formhydrazone amide was obtained in 0.45 g (oil).

Example 3
Synthesis of Methyl-N'-(2- (3-trifluoromethyl) -1,2,4-triazole-1-yl) -1-phenylpropyridene) formhydrazonate (compound number: A-122)
(2- (3-Trifluoromethyl) -1,2,4-triazole-1-yl) -1-phenylpropyridene) Hydrazide (1.00 g) is dissolved in toluene (5 ml), and methyl orthoformate (1 ml) is added. In addition, the reaction solution was refluxed for 10 hours. The organic solvent and the like are distilled off under reduced pressure, and the residue is purified by silica gel column chromatography and methyl-N'-(2- (3-trifluoromethyl) -1,2,4-triazole-1-yl) -1-phenylpropi. Liden) Holmhydrazonate was obtained in 0.6 g (oil).

Example 4
N-ethyl-N'-(2- (3-trifluoromethyl) -1,2,4-triazole-1-yl) -1-phenylpropyridene) formhydrazoneamide (compound numbers: A-133 and A-134) ) Synthesis Methyl-N'-(2- (3-trifluoromethyl) -1,2,4-triazole-1-yl) -1-phenylpropyridene) 0.4 g of formhydrazonate was dissolved in 2 ml of methanol. After adding 0.5 ml of 40% ethylamine ethanol solution and stirring at room temperature overnight, the organic solvent and the like were distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to purify N-ethyl-N'-(2- (3-trifluoromethyl). ) -1,2,4-Triazole-1-yl) -1-phenylpropyridene) 0.20 g (A-133, oil) of formhydrazone amide and 0.17 g (A-134, oil) of its geometric isomer. Got

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

Formulation Example 1 Emulsion The compound of the present invention (10 parts), xylene (60 parts), N-methyl-2-pyrrolidone (20 parts), Solpol 3005X (mixture of nonionic surfactant and anionic surfactant, Toho) Chemical Industry Co., Ltd. (trade name) (10 parts) was uniformly mixed and dissolved to obtain an emulsion.

Formulation Example 2 Wettable powder-1
Compound of the present invention (20 copies), Nipseal NS-K (White Carbon, Toso Silica Co., Ltd., trade name) (10 copies), Kaolin Clay (Kaolinite, Takehara Chemicals Co., Ltd., trade name) (60 copies) , Sun Extract P-252 (Sodium Lignin Sulfonate, Nippon Paper Chemicals Co., Ltd., trade name) (5 copies) and Lunox P-65L (alkylallyl sulfonate, Toho Chemical Industry Co., Ltd., trade name) (5 copies) Was uniformly mixed and pulverized with an air mill to obtain a wettable powder.

Formulation Example 3 Wettable powder-2
Compound of the present invention (20 parts), Nipseal NS-K (White Carbon, Toso Silica Co., Ltd., trade name) (20 parts), Kaolin Clay (50 parts), Lunox 1000C (Naphthalene sulfonate condensate, Toho Chemical Industry Co., Ltd.) Industrial Co., Ltd., trade name) (5 parts) and Solpol 5276 (nonionic surfactant, Toho Chemical Industry Co., Ltd., trade name) (5 parts) are uniformly mixed and pulverized with an air mill to prepare a wettable powder. Obtained.

Pharmaceutical example 4 Water solvent-1
The compound of the present invention (20 parts), Lunox P-65L (alkylallyl sulfonate, Toho Chemical Industry Co., Ltd., trade name) (3 parts), and water-soluble carrier (potassium chloride) (77 parts) are uniformly mixed and pulverized. Then, a water solvent was obtained.

Formulation Example 5 Water solvent-2
Uniformly apply the compound of the present invention (50 parts), New Calgen BX-C (Na alkylnaphthalene sulfonate, manufactured by Takemoto Yushi, trade name) (5 parts), silicon dioxide (2 parts), and water-soluble carrier (43 parts). Mixing and grinding was performed to obtain a water solvent.

Pharmaceutical example 6 Flowable agent-1
The present invention is added to a mixture of propylene glycol (5 parts), Solpol 7933 (anionic surfactant, Toho Chemical Industry Co., Ltd., trade name) (5 parts) and water (50 parts) that have been mixed in advance. The compound (20 parts) was dispersed to form a slurry-like mixture, and then the slurry-like mixture was wet-ground with Dynomill (Symmulenterprises), and then xanthan gum (0.2 parts) was well mixed with water (19.8 parts) in advance. The mixture and dispersion were added to obtain a flowable agent.

Pharmaceutical example 7 Flowable agent-2
Compound of the present invention (20 parts), Neucalgen FS-26 (mixture of dioctylsulfosuccinate and polyoxyethylene tristyrylphenyl ether, Takemoto Oil & Fat Co., Ltd., trade name) (5 parts), propylene glycol (8 parts), Water (50 parts) was mixed in advance, and this slurry-like mixture was wet-ground and pulverized with Dinomill (Symmal Enterprises). Next, xanthan gum (0.2 parts) was well mixed and dispersed in water (16.8 parts) to prepare a gel-like product, which was sufficiently mixed with the pulverized slurry to obtain a flowable agent.

Formulation Example 8 EW-1
The compound of the present invention (20 parts), Solpol CA-42 (non-ionic activator, Toho Chemical Industry Co., Ltd., trade name) (15 parts) and preservative Proxel GX-L (0.1 parts) are mixed and homogenized. After that, water (59.6 parts) was gradually added while stirring to obtain a dispersion. Xanthan gum obtained by adding antifoaming agent Antihome E-20 (emulsion type modified silicone type, Kao Co., Ltd., trade name) (0.1 part) to the obtained dispersion and dispersing it in propylene glycol (5.0 parts). (0.2 part) was added to obtain an emulsion preparation (phase inversion emulsification method).

Formulation Example 9 EW-2
The compound (10 parts) of the present invention was dissolved in xylene (10 parts) and mixed with the surfactant Leodor 430V (polyoxyethylene sorbitol tetraoleate, Kao Corporation, trade name) (24 parts). Liquid obtained in water (50.6 parts), antifoaming agent Antihome E-20 (emulsion type modified silicone type, Kao Co., Ltd., trade name) (0.1 parts), preservative Proxel GX-L (0 parts) 1. 1 part) was added and then dispersed using a homogenizer, and xanthan gum (0.2 parts) dispersed in propylene glycol (5.0 parts) was added to obtain an emulsion preparation (mechanical emulsification method).

Formulation Example 10 ME Agent-1
After mixing the compound of the present invention (0.01 part) and Solpol CA-42 (non-ionic activator, Toho Chemical Industry Co., Ltd., trade name) (0.1 part) to make it uniform, gradually water while stirring. (99.79 parts) was added. The preservative Proxel GX-L (0.1 part) was added to the dispersion to obtain a microemulsion.

Formulation Example 11 ME agent-2
The compound of the present invention (10 parts) and Newcalgen D-945 (polyoxyethylene (20 mol) sorbitan monooleate, Takemoto Oil & Fats Co., Ltd., trade name) (20 parts) were mixed and made uniform, and then stirred. Water (69.9 parts) was gradually added. The preservative Proxel GX-L (0.1 part) was added to the dispersion to obtain a microemulsion.

Formulation Example 12 ME agent-3
The compound of the present invention (0.01 part) was mixed with Solvent Solbesso 200 (0.08 part), Neucalgen ST-30 (polyoxyethylene arylphenyl ether formaldehyde condensate, polyoxyalkylene arylphenyl ether, alkylbenzene sulfonate and xylene). The mixture was dissolved in Takemoto Oil & Fat Co., Ltd. (trade name) (0.12 part), mixed with a surfactant, homogenized, and water (99.69 parts) was gradually added while stirring. The preservative Proxel GX-L (0.1 part) was added to the dispersion to obtain a microemulsion.

Pharmaceutical example 13 Granules-1
The compound of the present invention (5 parts), bentonite (30 parts), clay (60 parts), and sodium lignin sulfonate (5 parts) were uniformly pulverized and mixed, water was added and kneaded well, and then extruded granulation was performed. Granules were obtained by drying and sizing.

Formulation Example 14 Granule-2
The compound of the present invention (5 parts), sodium lignin sulfonate (4 parts), polyvinyl alcohol (PVA) (PVA) (PVA) (PVA) 0.5 part) and white carbon (0.5 part) were added, coated, and then dried and sized to obtain granules.

Formulation Example 15 Granules-3
The compound of the present invention (5 parts), sodium lignin sulfonate (3 parts), and sodium dioctyl sulfosuccinate, which had been pulverized and mixed in advance after putting Ishikawa Wright (89 parts) in a rolling granulator and impregnating it with water. (0.5 part), POE styrylphenyl ether (2 parts) and polyvinyl alcohol (PVA) (0.5 part) were added, coated, and then dried and sized to obtain granules.

Formulation Example 16 Fine Granules-1
The compound (2 parts) of the present invention was diluted with a solvent and mixed with pumice stone (98 parts) as a bulking agent while spraying the diluted solution. The obtained granular composition was dried and then sieved to obtain a fine granule.

Pharmaceutical example 17 Fine granules-2
The compound (5 parts) of the present invention is pulverized by air mill or mechanochemical pulverization as necessary. After uniformly mixing the powdered bulk material and silica sand (85 parts) as an bulking agent, the binder Toxanone GR-31A (10 parts) diluted with a solvent was mixed while spraying, and the obtained granular composition was dried. After that, it was sieved to obtain a fine granule.

Pharmaceutical Example 18 Powdered product The compound of the present invention (5 parts), white carbon (5 parts) and clay (trade name of Nippon Talc Co., Ltd.) (90 parts) were uniformly mixed and pulverized to obtain a powdered product.

Pharmaceutical Example 19 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 pulverized to obtain a powder.

Formulation Example 20 Seed-coated powder The compound of the present invention (10 parts), sodium lignin sulfonate (6 parts), polyvinyl alcohol (PVA) (1 part) and clay (trade name of Nippon Tarku Co., Ltd.) (83 parts) are uniformly applied. The powder prepared by mixing and crushing the seeds and the pre-moistened 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.

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 17th 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-3, A-4, A-5, A-6, A-7, A-8, A-9, A-10, A-11, A -12, A-13, A-14, A-15, A-17, A-19, A-25, A-26, A-27, A-29, A-30, A-31, A-32 , A-33, A-34, A-35, A-36, A-37, A-38, A-39, A-40, A-53, A-54, A-55, A-56, A -57, A-58, A-59, A-60, A-61, A-62, A-63, A-64, A-65, A-66, A-67, A-68, A-69 , A-70, A-71, A-72, A-73, A-80, A-81, A-82, A-83, A-84, A-85, A-90, A-91, A -92, A-93, A-94, A-95, A-96, A-102, A-105, A-107, A-108, A-110, A-113, A-114, A-116 , A-118, A-119, A-120, A-121, A-122, A-123, A-124, A-125, A-126, A-127, A-128, A-129, A -130, A-131, A-132, A-133, A-134, A-137, A-138, A-139, A-140, A-141, A-142, A-144, A-145 , A-146, A-147, A-148, A-149, A-150, A-151, A-152, A-154, A-155, A-156, A-157, A-158 books The invention compound showed a control value of 70% or more.

Test Example 2: 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 treatment plot As a result, compound numbers A-53, A-66, A-68, A-70, A-71, A-72, A-84, B-36, B-38 , B-55 of the present invention showed a control rate of 80%.

Claims (15)

The following formula (1)

[In the formula, R ₁ represents a hydrogen atom or a C _1-6 alkyl group.
R ₂ indicates a formyl group, or
R ₁ and R ₂ come together,

May form,
R ₄ indicates OR ₅ or NR ₆ R ₇
R ₅ is C _1-6 alkyl 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 Alkyl C _1-6 Alkyl Group, C _3-6 Cycloalkyl Group, C _3-6 Cycloalkyl C _1-6 Alkyl Group or benzyl Group.
R ₆ represents a hydrogen atom or a C _1-6 alkyl group.
R ₇ is a hydrogen atom, C _1-6 alkyl 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 ₆ and R ₇ may be bonded to each other to form a saturated or unsaturated 4- to 7-membered ring with the nitrogen atom to which R ₆ and R ₇ are bonded.
R ₃ indicates a C _1-6 alkyl group or phenyl 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 alkoxy group If a coxycarbonyl group, formyl group, halogen atom, cyano group or nitro group is indicated, or if two Xs are present in place of a hydrogen atom on two adjacent carbon atoms, the above two X may be combined with the carbon atoms to which each is bonded to form a saturated or unsaturated 5- or 6-membered ring.
n indicates an integer from 1 to 5
Y ₁ , Y ₂ , Y ₃ and Y ₄ independently represent a nitrogen atom or CR group, respectively.
R is independently a hydrogen atom, a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _1-6 alkylthio group, a C _1-6 alkyl sulfinyl group, a C _1-6 alkyl sulfonyl group, and a C _1- . ₆ Shows an alkoxy group, a C _1-6 alkyloxycarbonyl group, a halogen atom, a cyano group or a nitro group. ]
Hydrazone derivative represented by, or a salt thereof. The hydrazone derivative according to claim 1, or a salt thereof, wherein Y ₂ indicates CR, R indicates a C _1-6 haloalkyl group, and R ₃ indicates a methyl group or an ethyl group. The following formula (2)

[In the formula, R ₁ represents a hydrogen atom or a C _1-6 alkyl group.
R ₃ indicates a C _1-6 alkyl group or phenyl 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 alkoxy group If a coxycarbonyl group, a formyl group, a halogen atom, a cyano group or a nitro group is indicated, or if two Xs are present in place of a hydrogen atom on two adjacent carbon atoms, the above two X may be combined with the carbon atoms to which each is bonded to form a saturated or unsaturated 5- or 6-membered ring.
n indicates an integer from 1 to 5
Y ₁ , Y ₂ , Y ₃ and Y ₄ independently represent a nitrogen atom or CR group, respectively.
R is independently a hydrogen atom, a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _1-6 alkylthio group, a C _1-6 alkyl sulfinyl group, a C _1-6 alkyl sulfonyl group, and a C _1- . ₆ Shows an alkoxy group, a C _1-6 alkyloxycarbonyl group, a halogen atom, a cyano group or a nitro group. ]
Hydrazone derivative represented by. The following formula (3)

[In the formula, R ₃ represents a C _1-6 alkyl group or phenyl 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 alkoxy group If a coxycarbonyl group, a formyl group, a halogen atom, a cyano group or a nitro group is indicated, or if two Xs are present in place of a hydrogen atom on two adjacent carbon atoms, the above two X may be combined with the carbon atoms to which each is bonded to form a saturated or unsaturated 5- or 6-membered ring.
n indicates an integer from 1 to 5
Y ₁ , Y ₂ , Y ₃ and Y ₄ independently represent a nitrogen atom or CR group, respectively.
R is independently a hydrogen atom, a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _1-6 alkylthio group, a C _1-6 alkyl sulfinyl group, a C _1-6 alkyl sulfonyl group, and a C _1- . ₆ Shows an alkoxy group, a C _1-6 alkyloxycarbonyl group, a halogen atom, a cyano group or a nitro group. ]
Ketone derivative represented by. The following formula (4)

[In the formula, R ₁ represents a hydrogen atom or a C _1-6 alkyl group.
R ₃ indicates a C _1-6 alkyl group or phenyl 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 alkoxy group If a coxycarbonyl group, a formyl group, a halogen atom, a cyano group or a nitro group is indicated, or if two Xs are present in place of a hydrogen atom on two adjacent carbon atoms, the above two X may be combined with the carbon atoms to which each is bonded to form a saturated or unsaturated 5- or 6-membered ring.
n indicates an integer from 1 to 5
Y ₁ , Y ₂ , Y ₃ and Y ₄ independently represent a nitrogen atom or CR group, respectively.
R is independently a hydrogen atom, a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _1-6 alkylthio group, a C _1-6 alkyl sulfinyl group, a C _1-6 alkyl sulfonyl group, and a C _1- . ₆ Shows an alkoxy group, a C _1-6 alkyloxycarbonyl group, a halogen atom, a cyano group or a nitro group. ]
It is a method for producing a hydrazone derivative represented by.
The following formula (2)

[In the equation, R ₁ , R ₃ , X, Y ₁ , Y ₂ , Y ₃ , Y ₄ and n are as defined in equation (4). ]
Hydrazone derivative represented by, formic acid and / or the following formula (5)
HCOOR ₈ (5)
[In the formula, R ₈ represents a C _1-6 alkyl group. ]
A production method comprising reacting with a formate ester represented by. The following formula (6)

[In the formula, R ₄ indicates OR ₅ or NR ₆ R ₇ and
R ₅ is C _1-6 alkyl 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 Alkyl C _1-6 Alkyl Group, C _3-6 Cycloalkyl Group, C _3-6 Cycloalkyl C _1-6 Alkyl Group or benzyl Group.
R ₆ represents a hydrogen atom or a C _1-6 alkyl group.
R ₇ is a hydrogen atom, C _1-6 alkyl 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 ₆ and R ₇ may be bonded to each other to form a saturated or unsaturated 4- to 7-membered ring with the nitrogen atom to which R ₆ and R ₇ are bonded.
R ₃ indicates a C _1-6 alkyl group or phenyl 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 alkoxy group If a coxycarbonyl group, a formyl group, a halogen atom, a cyano group or a nitro group is indicated, or if two Xs are present in place of a hydrogen atom on two adjacent carbon atoms, the above two X may be combined with the carbon atoms to which each is bonded to form a saturated or unsaturated 5- or 6-membered ring.
n indicates an integer from 1 to 5
Y ₁ , Y ₂ , Y ₃ and Y ₄ independently represent a nitrogen atom or CR group, respectively.
R is independently a hydrogen atom, a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _1-6 alkylthio group, a C _1-6 alkyl sulfinyl group, a C _1-6 alkyl sulfonyl group, and a C _1- . ₆ Shows an alkoxy group, a C _1-6 alkyloxycarbonyl group, a halogen atom, a cyano group or a nitro group. ]
It is a method for producing a hydrazone derivative represented by.
The following formula (2)

[In the equation, R ₁ indicates a hydrogen atom, and R ₃ , X, Y ₁ , Y ₂ , Y ₃ , Y ₄ and n are as defined in equation (6). ]
Hydrazone derivative represented by and the following formula (7)

[In the formula, R ₄ is as defined in formula (6), and R ₈ 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. The following formula (8)

[In the formula, R ₆ represents a hydrogen atom or a C _1-6 alkyl group.
R ₇ is a hydrogen atom, C _1-6 alkyl 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 ₆ and R ₇ may bond to each other to form a saturated or unsaturated 4- to 7-membered ring with the nitrogen atom to which R ₆ and R ₇ are bonded.
R ₃ indicates a C _1-6 alkyl group or phenyl 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 alkoxy group If a coxycarbonyl group, formyl group, halogen atom, cyano group or nitro group is indicated, or if two Xs are present in place of a hydrogen atom on two adjacent carbon atoms, the above two X may be combined with the carbon atoms to which each is bonded to form a saturated or unsaturated 5- or 6-membered ring.
n indicates an integer from 1 to 5
Y ₁ , Y ₂ , Y ₃ and Y ₄ independently represent a nitrogen atom or CR group, respectively.
R is independently a hydrogen atom, a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _1-6 alkylthio group, a C _1-6 alkyl sulfinyl group, a C _1-6 alkyl sulfonyl group, and a C _1- . ₆ Shows an alkoxy group, a C _1-6 alkyloxycarbonyl group, a halogen atom, a cyano group or a nitro group. ]
It is a method for producing a hydrazone derivative represented by.
The following formula (9)

[In the formula, R ₃ , X, Y ₁ , Y ₂ , Y ₃ , Y ₄ and n are as defined in formula (8), and R ₈ represents a C _1-6 alkyl group. ]
Hydrazone derivative represented by and the following formula (10)

[In the equation, R ₆ and R ₇ are as defined in equation (8). ]
A production method comprising reacting with an amine derivative represented by. The following formula (2)

[In the formula, R ₁ represents a hydrogen atom or a C _1-6 alkyl group.
R ₃ indicates a C _1-6 alkyl group or phenyl 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 alkoxy group If a coxycarbonyl group, formyl group, halogen atom, cyano group or nitro group is indicated, or if two Xs are present in place of a hydrogen atom on two adjacent carbon atoms, the above two X may be combined with the carbon atoms to which each is bonded to form a saturated or unsaturated 5- or 6-membered ring.
n indicates an integer from 1 to 5
Y ₁ , Y ₂ , Y ₃ and Y ₄ independently represent a nitrogen atom or CR group, respectively.
R is independently a hydrogen atom, a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _1-6 alkylthio group, a C _1-6 alkyl sulfinyl group, a C _1-6 alkyl sulfonyl group, and a C _1- . ₆ Shows an alkoxy group, a C _1-6 alkyloxycarbonyl group, a halogen atom, a cyano group or a nitro group. ]
It is a method for producing a hydrazone derivative represented by.
The following formula (3)

[In the equation, R ₃ , X, Y ₁ , Y ₂ , Y ₃ , Y ₄ , and n are as defined in equation (2). ]
The ketone derivative represented by the following formula (11)

[In the equation, R ₁ is as defined in equation (2). ]
A production method comprising reacting with a hydrazine derivative represented by. An agricultural and horticultural agent containing the hydrazone derivative according to any one of claims 1 and 2 or a salt thereof. A nematode control agent for agriculture and horticulture containing the hydrazone derivative according to any one of claims 1 and 2 or a salt thereof. An agricultural and horticultural pest control agent containing the hydrazone derivative according to any one of claims 1 and 2 or a salt thereof. A horticultural disease control agent containing the hydrazone derivative according to any one of claims 1 and 2 or a salt thereof. A method for controlling plant pests, comprising treating pests and / or their habitats and / or seeds and / or plant propagation materials with the agricultural and horticultural agents according to claim 9. A method for preventing plant pests, which comprises 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. 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.