JP2024056194A - New hydrazone derivatives and agricultural and horticultural agents containing the same as active ingredients - Google Patents

Abstract

[Problem] To provide a compound that exhibits excellent effects as an agricultural and horticultural agent, particularly as an agricultural and horticultural pest control agent or nematode control agent. [Solution] The compound represented by the following formula is provided. TIFF2024056194000065.tif3063 (wherein R3 and R4 each independently represent a C1-6 alkyl group.) [Selected Figure] None

Description

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

In the agricultural and horticultural fields, plant pest control agents have been developed and put to practical use in order to control various pests. However, the emergence of pests or diseases that have acquired drug resistance has become a problem, and the development of new agents is eagerly awaited.
Patent Document 1 describes that semicarbazone derivatives are useful as agricultural insecticides. However, Patent Document 1 does not disclose hydrazone compounds such as those of the present invention. Furthermore, Patent Document 1 does not disclose any effect on nematodes with respect to the compounds described therein.
Patent Document 2 describes compounds similar to the compounds of the present invention as agricultural nematode control agents, but does not disclose a compound having two alkyl groups on the carbon atom to which the azole group is bonded, as in the present invention.
In addition, other documents disclose compounds similar to the compounds of the present invention (e.g., Patent Documents 3 to 5). However, none of Patent Documents 3 to 5 discloses a compound having two alkyl groups on the carbon atom to which the azole group is bonded.

Japanese Patent Application Laid-Open No. 8-073436 International Publication No. 2020/179910 WO 01/36381 JP 2002-155044 A WO 93/19045

Damage caused by pests and diseases remains significant in agricultural and horticultural crop production, and the development of new agricultural and horticultural pesticides is desired due to factors such as the emergence of pests resistant to existing drugs.

[式中、R₁は、水素原子、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_2-6アルケニル基、Ｃ_2-6アルキニル基又は置換されていてもよいベンジル基を示し、
R₂は、ホルミル基を示し、又は
R₁とR₂とは一緒になって、次式、

で表される基を形成してもよく、
R₅は、OR₆又はNR₇R₈を示し、
R₆は、Ｃ_1-6アルキル基又はＣ_1-6ハロアルキル基を示し、
R₇は、水素原子又はＣ_1-6アルキル基を示し、
R₈は、水素原子、Ｃ_1-6アルキル基、Ｃ_1-6ハロアルキル基、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Ｃ_1-6アルキル基、Ｃ_1-6アルコキシ基、Ｃ_2-6アルケニル基、Ｃ_2-6ハロアルケニル基、Ｃ_2-6アルキニル基、Ｃ_2-6ハロアルキニル基、Ｃ_3-6シクロアルキル基、又は置換されていてもよいベンジル基を示し、又は
R₇とR₈とは、それらが結合している窒素原子と一緒になって、飽和又は不飽和の4～7員環を形成してもよく、
R₃及びR₄は、それぞれ独立して、Ｃ_1-6アルキル基を示し、
Xは、又はXが複数で存在する場合には複数のXはそれぞれ独立して、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_3-6ハロシクロアルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6ハロアルケニル基、Ｃ_2-6アルキニル基、Ｃ_2-6ハロアルキニル基、Ｃ_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_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、又は、隣接する２個の炭素原子上に存在する２個のXは、それぞれのX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、１～５の整数を示し、
Y₁、Y₂、Y₃及びY₄は、それぞれ独立して、窒素原子又はCR基を示し、
Rは、又はRが複数で存在する場合には複数のRはそれぞれ独立して、水素原子、Ｃ_1-6ハロアルキル基、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又は線虫防除剤、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。 Means for Solving the Problems The present inventors have conducted intensive research to solve the above problems, and as a result have found that a hydrazone derivative represented by the following formula (1), which is a novel compound not described in the literature, is useful as an agricultural and horticultural agent, in particular as an agricultural and horticultural pest control agent or a nematode control agent, and have thus completed the present invention.
That is, the present invention provides a compound represented by the following formula (1):

[In the formula, R ₁ represents a hydrogen atom, a C _1-6 alkyl group, a C _1-6 alkoxy C _1-6 alkyl group, a C _2-6 alkenyl group, a C _2-6 alkynyl group or an optionally substituted benzyl group,
_R2 represents a formyl group, or
R ₁ and R ₂ together represent the following formula:

may form a group represented by
_R5 represents _{OR6 or NR7R8} ;
_R6 represents a _C1-6 alkyl group or a _C1-6 haloalkyl group;
_R7 represents a hydrogen atom or a _C1-6 alkyl group;
_R8 represents a hydrogen atom, a _C1-6 alkyl group, a _C1-6 haloalkyl group, a _hydroxyC1-6 alkyl group, a _{C1-6 alkoxyC1-6} alkyl group, _{a C3-6} cycloalkylC1-6 alkyl group, a _C1-6 alkoxy group, a _C2-6 alkenyl group, a _C2-6 haloalkenyl group, a _C2-6 alkynyl group, a _C2-6 haloalkynyl group, a _C3-6 cycloalkyl group, or an optionally substituted benzyl group; or
R ₇ and R ₈ together with the nitrogen atom to which they are attached may form a saturated or unsaturated 4- to 7-membered ring;
_R3 and _R4 each independently represent a _C1-6 alkyl group;
X, or when a plurality of Xs are present, each of the plurality of Xs independently represents a hydrogen atom, a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _3-6 cycloalkyl group, a C _3-6 halocycloalkyl group, a C _2-6 alkenyl group, a C _2-6 haloalkenyl group, a C _2-6 alkynyl group, a C _2-6 haloalkynyl group, a C _1-6 alkoxy group, a C _1-6 haloalkoxy group, a C _1-6 alkylthio group, a C _1-6 alkylsulfinyl group, a C _1-6 alkylsulfonyl group, a C _1-6 alkoxycarbonyl group, a formyl group, a halogen atom, a cyano group or a nitro group, or two Xs present on two adjacent carbon atoms may form a saturated or unsaturated 5- or 6-membered ring together with the carbon atoms to which each X is bonded,
n represents an integer from 1 to 5;
Y ₁ , Y ₂ , Y ₃ and Y ₄ each independently represent a nitrogen atom or a CR group;
R, or when there are multiple R, each of the multiple Rs independently represents a hydrogen atom, a _C1-6 haloalkyl group, a halogen atom, a cyano group, or a nitro group.
or a salt thereof, and further relates to an agricultural and horticultural agent, particularly an agricultural and horticultural pest control agent or nematode control agent, containing said compound as an active ingredient, a method for using the same, and a method for producing said compound, etc.

The compounds of the present invention are highly effective as agricultural and horticultural pesticides, particularly as agricultural and horticultural pest control agents or nematode control agents. They are also effective against pests that parasitize pets such as dogs and cats, and livestock such as cows and sheep.

The definition of a substituent "halogen atom" refers to a chlorine atom, a bromine atom, an iodine atom or a fluorine atom.
The "C _1-6 alkyl group" refers to a straight-chain or branched-chain alkyl group having 1 to 6, preferably 1 to 4, carbon atoms, such as a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, an s-butyl group, a t-butyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, an n-hexyl group, or an isohexyl group.
The term "C _1-6 haloalkyl group" refers to an alkyl group in which any carbon atom in the above-mentioned alkyl group is substituted with a halogen atom. Examples of the C _1-6 haloalkyl group include a linear or branched haloalkyl group having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, substituted with preferably 1 to 9 halogen atoms, such as 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, a 2-fluoroethyl group, a 2-chloroethyl group, a 2-bromoethyl group, a 2-iodoethyl group, a 2,2,2-trifluoroethyl group, a 2,2,2-trichloroethyl group, a pentafluoroethyl group, a 2,2-difluoroethyl group, a 1-fluoroisopropyl group, a 3-fluoropropyl group, a 3-chloropropyl group, a 3-bromopropyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a 4-fluorobutyl group, a 4-chlorobutyl group, a nonafluorobutyl group, or the like.

The "hydroxy _C1-6 alkyl group" refers to an alkyl group substituted with a hydroxyl group at any carbon atom in the above-mentioned alkyl group. Examples of the hydroxy _C1-6 alkyl group include a hydroxymethyl group, a 2-hydroxyethyl group, a 2-hydroxypropyl group, a 3-hydroxypropyl group, and a 3-hydroxy-2,2-dimethylpropyl group.
The "C _1-6 alkoxy group" is a group having an oxygen atom between the carbon atoms in the carbon-carbon bond of an alkyl group, and examples thereof include linear or branched alkoxy groups having 1 to 6, preferably 1 to 4, carbon atoms, such as a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxy group, a tert-butoxy group, an n-pentoxy group, or an n-hexyloxy group.
The term "C _1-6 alkoxy C _1-6 alkyl group" refers to the above alkyl group substituted at any carbon atom with the above C _1-6 alkoxy group. Examples of the C _1-6 alkoxy C _1-6 alkyl group include a methoxymethyl group, an ethoxymethyl group, a methoxyethyl group, an ethoxyethyl group, and a 3-methoxypropyl group.
The term "C _3-6 cycloalkyl group" refers to a cyclic alkyl group, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc., having 3 to 6 carbon atoms, preferably 1 to 3 carbon atoms.

The term " _C3-6 cycloalkyl _C1-6 alkyl group" refers to an alkyl group substituted at any carbon atom with the above _C3-6 cycloalkyl group in the above alkyl group. Examples of the _C3-6 cycloalkyl _C1-6 alkyl group include cyclopropylmethyl, 2-cyclopropylethyl, 3-cyclopropylpropyl, 4-cyclopropylbutyl, 5-cyclopropylpentyl, 6-cyclopropylhexyl, cyclobutylmethyl, cyclopentylmethyl and the like.
The term "C _3-6 halocycloalkyl group" refers to a cycloalkyl group in which any carbon atom in the above C _3-6 cycloalkyl group is substituted by a halogen atom, and examples thereof include halocycloalkyl groups having 3 to 6, preferably 3 to 5, carbon atoms, preferably substituted by 1 to 9 halogen atoms, such as 1-fluorocyclopropyl, 2-fluorocyclopropyl, 2,2-difluorocyclopropyl, 2,2,3,3-tetrafluorocyclopropyl, 1-chlorocyclopropyl, 2-chlorocyclopropyl, 2,2-dichlorocyclopropyl, 2,2,3,3-tetrachlorocyclopropyl, 2,2-dibromocyclopropyl, 1-fluorocyclobutyl, 2-fluorocyclobutyl, 3-fluorocyclobutyl, 3,3-difluorocyclobutyl, 3,3-dichlorocyclobutyl, 1-fluorocyclopentyl, 2-fluorocyclopentyl, 3-fluorocyclopentyl, 2,2-difluorocyclopentyl, 3,3-difluorocyclopentyl 2,2-dichlorocyclopentyl, and 1-fluorocyclohexyl groups.

The "C _1-6 haloalkoxy group" refers to an alkoxy group in which any carbon atom of the C _1-6 alkoxy group explained above is substituted with a halogen atom, and examples thereof include linear or branched haloalkoxy groups having 1 to 6 carbon atoms, preferably 1 to 3 carbon atoms, substituted preferably with 1 to 9 halogen atoms, such as a fluoromethoxy group, a dichloromethoxy group, a trichloromethoxy group, a difluoromethoxy group, a trifluoromethoxy group, a chlorodifluoromethoxy group, a bromodifluoromethoxy group, a dichlorofluoromethoxy group, a 1-fluoroethoxy group, a 2-fluoroethoxy group, a 2-chloroethoxy group, a 2-bromoethoxy group, a 2-iodoethoxy group, a 2,2,2-trifluoroethoxy group, a 2,2,2-trichloroethoxy group, a pentafluoroethoxy group, a 1-fluoroisopropoxy group, a 3-fluoropropoxy group, a 3-chloropropoxy group, a 3-bromopropoxy group, a 4-fluorobutoxy group, and a 4-chlorobutoxy group.

The " _C2-6 alkenyl group" refers to an alkyl group having a carbon-carbon double bond at any position, and examples thereof include straight-chain or branched-chain alkenyl groups having 2 to 6, preferably 3 to 4, carbon atoms, such as vinyl group, allyl group, isopropenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1,1-dimethyl-2-propenyl group, 1-ethyl-2-propenyl group, 1-methyl-2-butenyl group, 1-methyl-3-butenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group, 1,1-dimethyl-2-butenyl group, and 1,1-dimethyl-3-butenyl group.
The " _C2-6 haloalkenyl group" refers to the above-mentioned alkenyl group in which any of the carbon atoms is substituted with a halogen atom, and examples thereof include linear or branched halogenated alkenyl groups having 2 to 6, preferably 3 to 4, carbon atoms and preferably substituted with 1 to 9 halogen atoms, such as a 1-fluorovinyl group, a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 3-chloro-2-propenyl group, a 3,3-difluoro-2-allyl group, a 3,3-dichloro-2-allyl group, a 4,4,4-trifluoro-2-butenyl group, a 4,4,4-trifluoro-3-butenyl group, a 5-chloro-3-pentenyl group, or a 6-fluoro-2-hexenyl group.
The "C _2-6 alkynyl group" refers to an alkyl group having a carbon-carbon triple bond at any position, and examples thereof include linear or branched alkynyl groups having 2 to 6, preferably 3 to 4, carbon atoms, such as ethynyl group, 2-propynyl group, 1-methyl-2-propynyl group, 1,1-dimethyl-2-propynyl group, 1-butynyl group, 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-butynyl group, 1,1-dimethyl-3-butynyl group, 1-methyl-3-pentynyl group, and 1-methyl-4-pentynyl group.

The “C _2-6 haloalkynyl group” refers to the above-mentioned alkynyl group in which any of the carbon atoms is substituted with a halogen atom, and examples thereof include a fluoroethynyl group, a 4,4,4-trifluoro-2-butynyl group, a 5,5,5-trifluoro-3-pentynyl group, a 1-methyl-3,3,3-trifluoro-2-butynyl group, a 1-methyl-5,5,5-trifluoro-2-pentynyl group, etc., preferably a linear or branched halogenated alkynyl group having 2 to 6, preferably 3 or 4, carbon atoms substituted with 1 to 9 halogen atoms.

The "optionally substituted benzyl group" means a benzyl group in which a hydrogen atom at any carbon atom of the benzyl group is substituted with another substituent, and examples of such a substituent include a _C1-6 alkyl group, a halogen atom, a _C1-6 alkoxy group, a _C1-6 haloalkyl group, and a _C1-6 haloalkoxy group.
The term "C _1-6 alkoxycarbonyl group" means a carbonyl group substituted by the above alkoxy group, and examples of the C _1-6 alkoxycarbonyl group include methoxycarbonyl, ethoxycarbonyl, n-propylcarbonyl, n-butylcarbonyl, n-pentylcarbonyl, n-hexylcarbonyl, and i-propylcarbonyl groups.

The "C _1-6 alkylthio group" is a thio group substituted by the above-mentioned alkyl group, and examples of the C _1-6 alkylthio group include alkylthio groups such as a methylthio group, an ethylthio group, an n-propylthio group, an isopropylthio group, an n-butylthio group, an s-butylthio group, a t-butylthio group, an n-pentylthio group, and an n-hexylthio group.

The _C1-6 alkylsulfinyl group is a sulfinyl group substituted by the above-mentioned alkyl group, and examples of the _C1-6 alkylsulfinyl group include alkylsulfinyl groups such as a methylsulfinyl group, an ethylsulfinyl group, an n-propylsulfinyl group, an isopropylsulfinyl group, an n-butylsulfinyl group, an s-butylsulfinyl group, a t-butylsulfinyl group, an n-pentylsulfinyl group and an n-hexylsulfinyl group.
The _C1-6 alkylsulfonyl group is a sulfonyl group substituted by the above-mentioned alkyl group, and examples of the _C1-6 alkylsulfonyl group include alkylsulfonyl groups such as a methylsulfonyl group, an ethylsulfonyl group, an n-propylsulfonyl group, an isopropylsulfonyl group, an n-butylsulfonyl group, an s-butylsulfonyl group, a t-butylsulfonyl group, an n-pentylsulfonyl group, and an n-hexylsulfonyl group.

In the above formula (1), the 4- to 7-membered ring in " _R7 and _R8 may form a saturated or unsaturated 4- to 7-membered ring together with the nitrogen atom to which they are bonded" may be either saturated or unsaturated. Examples of such 4- to 7-membered rings include saturated rings such as a pyrrolidine ring, a piperidine ring, a morpholine ring, a thiomorpholine ring, and a hexamethyleneimine ring, and examples of unsaturated rings include pyrazole, imidazole, 1,3,4-triazole, 1,2,3-triazole, and tetrazole.
In the above formula (1), the 5- or 6-membered ring in "two Xs present on two adjacent carbon atoms may form a saturated or unsaturated 5- or 6-membered ring together with the carbon atoms to which each X is bonded" may be a carbocyclic or heterocyclic ring, for example, an indan ring, a tetrahydronaphthalene ring, a naphthalene ring, etc., condensed with a phenyl ring. In such a 5- or 6-membered ring, the two Xs present by replacing hydrogen atoms on two adjacent carbon atoms of the phenyl ring may be, for example, _{-CH2CH2CH2- , -CH2CH2CH2CH2-} , -CH ₌ CHCH _{= CH- ,} -N=CHCH=CH-, _-OCHCHCH2- , etc.

Examples of the salt of the hydrazone derivative represented by the above formula (1) include inorganic acid salts such as hydrochloride, sulfate, nitrate, and phosphate, and organic acid salts such as acetate, fumarate, maleate, oxalate, methanesulfonate, benzenesulfonate, and p-toluenesulfonate.
The compound of the present invention may contain one or more asymmetric centers in its structural formula, and may exist as two or more optical isomers and diastereomers, and the concept of the compound of the present invention encompasses all of the optical isomers and mixtures containing them in any ratio. In addition, the compound of the present invention may contain two or more geometric isomers derived from a carbon-carbon double bond or a carbon-nitrogen double bond in its structural formula, and the concept of the compound of the present invention encompasses all of the geometric isomers and mixtures containing them in any ratio.
In the compounds of the present invention, the wavy line in the structural formula represents any one of two or more geometric isomers derived from a carbon-carbon double bond or a carbon-nitrogen double bond.

In the hydrazone derivative represented by the above formula (1), _Y2 is preferably CR.
In the hydrazone derivative represented by the above formula (1), R is preferably a C _1-6 haloalkyl group.
In the hydrazone derivative represented by the above formula (1), it is preferable that _R3 and _R4 are each a methyl group.
In the hydrazone derivative represented by the above formula (1), it is more preferable that _Y2 represents CR, R represents a _C1-6 haloalkyl group, and _R3 and _R4 represent methyl groups.

[式中、
R₃及びR₄は、それぞれ独立して、Ｃ_1-6アルキル基を示し、
Xは、又はXが複数で存在する場合には複数のXはそれぞれ独立して、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_3-6ハロシクロアルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6ハロアルケニル基、Ｃ_2-6アルキニル基、Ｃ_2-6ハロアルキニル基、Ｃ_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_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、又は、隣接する２個の炭素原子上に存在する２個のXは、それぞれのX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、１～５の整数を示し、
Y₁、Y₂、Y₃及びY₄は、それぞれ独立して、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ハロアルキル基、ハロゲン原子、シアノ基又はニトロ基を示し、そして
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（１５）で表されるα－ハロゲンケトン化合物と前記式（１６）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。
なお、式（１５）で表されるα－ハロゲンケトン化合物及び式（１６）のアゾール化合物は、例えば、特開2021-24823号公報に記載されている方法などにより、当業者であれば、直ちに調製可能である。 Representative methods for producing the hydrazone derivative represented by formula (1) of the present invention, its intermediate hydrazone derivative represented by formula (2), and ketone derivative represented by formula (3) will be described below. However, the scope of the present invention is not limited in any way by these exemplified production methods, and also includes any appropriately modified production methods by those skilled in the art.
Reaction Scheme 1

[Wherein,
_R3 and _R4 each independently represent a _C1-6 alkyl group;
X, or when a plurality of Xs are present, each of the plurality of Xs independently represents a hydrogen atom, a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _3-6 cycloalkyl group, a C _3-6 halocycloalkyl group, a C _2-6 alkenyl group, a C _2-6 haloalkenyl group, a C _2-6 alkynyl group, a C _2-6 haloalkynyl group, a C _1-6 alkoxy group, a C _1-6 haloalkoxy group, a C _1-6 alkylthio group, a C _1-6 alkylsulfinyl group, a C _1-6 alkylsulfonyl group, a C _1-6 alkoxycarbonyl group, a formyl group, a halogen atom, a cyano group or a nitro group, or two Xs present on two adjacent carbon atoms may form a saturated or unsaturated 5- or 6-membered ring together with the carbon atoms to which each X is bonded,
n represents an integer from 1 to 5;
Y ₁ , Y ₂ , Y ₃ and Y ₄ each independently represent a nitrogen atom or a CR group;
R each independently represents a hydrogen atom, a _C1-6 haloalkyl group, a halogen atom, a cyano group, or a nitro group; and
Hal represents a halogen atom.
In the method shown in reaction scheme 1, the ketone derivative represented by the formula (3) can be produced by reacting an α-halogen ketone compound represented by the formula (15) with an azole compound represented by the formula (16) in the presence or absence of a base in an inert solvent.
In addition, the α-halogen ketone compound represented by formula (15) and the azole compound represented by formula (16) can be readily prepared by a person skilled in the art, for example, by the method described in JP-A-2021-24823.

As the solvent used in the reaction of the compound of formula (15) with the compound of formula (16), a wide variety of known solvents can be used as long as they are inert to the reaction. Examples of such solvents include aliphatic or alicyclic hydrocarbon solvents such as hexane, cyclohexane, and heptane, aromatic hydrocarbon solvents such as benzene, chlorobenzene, toluene, and xylene, halogenated hydrocarbon solvents such as methylene chloride, 1,2-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, amide solvents such as N,N-dimethylformamide, nitrile solvents such as acetonitrile and propionitrile, and aprotic polar solvents such as N-methylpyrrolidone and N,N'-dimethylimidazolinone. These solvents can be used alone or in combination of two or more as necessary.
As the base used in the reaction of the compound of formula (15) with the compound of formula (16), known inorganic 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 hydrides such as sodium hydride and potassium hydride. 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 combination of two or more.
Such a base can be used in an amount of usually 1 to 100 equivalents, preferably 1 to 2 equivalents, based on the ketone compound represented by the formula (15).

The ratio of the α-halogen ketone compound represented by the formula (15) to the azole compound represented by the formula (16) is more preferably 1 to 1.2 moles of compound (16) relative to compound (15).
The reaction can usually be carried out within a temperature range of from -78°C to the boiling point of the solvent used, and is preferably carried out at room temperature to 100°C.
The reaction time varies depending on the reaction temperature etc. and cannot be generalized, but the reaction is usually completed within 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, such as organic solvent extraction, chromatography, recrystallization, distillation, etc., and can be further purified by a commonly used purification means.

［式中、R₁は、水素原子、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_2-6アルケニル基、Ｃ_2-6アルキニル基又は置換されていてもよいベンジル基を示し、X、Y₁、Y₂、Y₃、Y₄、R₃、R₄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（１４）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 Scheme 2

[In the formula, _R1 represents a hydrogen atom, a _C1-6 alkyl group, a _C1-6 alkoxy _C1-6 alkyl group, a _C2-6 alkenyl group, a _C2-6 alkynyl group, or an optionally substituted benzyl group, and X, _Y1 , _Y2 , _Y3 , _Y4 , _R3 , _R4 , and n are as defined in the formula (3).]
In the method shown in reaction scheme 2, the hydrazone derivative represented by the formula (2) can be produced by reacting the ketone compound represented by the formula (3) with the hydrazine compound represented by the formula (14) in an inert solvent in the presence or absence of an acid.

The solvent used in the reaction of the ketone derivative of the formula (3) with the hydrazine compound of the formula (14) can be a wide variety of known solvents as long as they are inert to the reaction. Examples of such solvents include alcohols such as methanol, ethanol, n-propanol, and iso-propanol; aliphatic or alicyclic hydrocarbon solvents such as hexane, cyclohexane, and heptane; aromatic hydrocarbon solvents such as benzene, chlorobenzene, toluene, and xylene; halogenated hydrocarbon solvents such as methylene chloride, 1,2-dichloroethane, and chloroform; ether solvents such as diethyl ether, tetrahydrofuran, and 1,4-dioxane; ester solvents such as methyl acetate and ethyl acetate; amide solvents such as N,N-dimethylformamide; N-methylpyrrolidone, N,N'-dimethylimidazolinone, and acetonitrile. These solvents can be used alone or in combination of two or more as necessary.
Known inorganic and organic acids can be used as the acid used in the reaction between the compound of formula (3) and the compound of formula (14). Examples of inorganic acids include hydrogen chloride, hydrogen bromide, sulfuric acid, and nitric acid. Examples of organic acids include acetic acid, propionic acid, citric acid, methanesulfonic acid, ethanesulfonic acid, and p-toluenesulfonic acid. These acids can be used alone or in combination of two or more.
Such an acid can be used in an amount of 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 of the formula (14) used can be appropriately selected from a wide range. The ratio of the latter to the former is preferably 1 to 10 moles, more preferably 2.0 to 5.0 moles.
The reaction is preferably carried out at a temperature between 0° C. and the boiling point of the solvent used, and more preferably at room temperature to under reflux.
The reaction time varies depending on the reaction temperature etc. and cannot be generalized, but the reaction is usually completed within about 0.1 to 24 hours.
After the reaction is completed, the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purifying the product, if necessary, by recrystallization, column chromatography, etc. Alternatively, the target product may be used in the next reaction step without being isolated from the reaction system.

［式中、R₉は、Ｃ_1-6アルキル基を示し、X, Y₁, Y₂, Y₃, Y₄, R₁, R₃, R₄及びnは、前記式（２）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 Scheme 3

[In the formula, _R9 represents a _C1-6 alkyl group, and X, _Y1 , _Y2 , _Y3 , _Y4 , _R1 , _R3 , _R4 and n are as defined in the formula (2).]

In the method shown in reaction scheme 3, the hydrazone derivative represented by the formula (4) can be produced by a formylation reaction between the hydrazone derivative represented by the formula (2) and formic acid and/or the formic acid derivative represented by the formula (5).

The solvent used in the formylation reaction of the hydrazone compound represented by the formula (2) may be any of a wide variety of known solvents, so long as they are inert to the reaction. Examples of such solvents include aliphatic or alicyclic hydrocarbon solvents such as hexane, cyclohexane, and heptane; aromatic hydrocarbon solvents such as benzene, chlorobenzene, toluene, and xylene; halogenated hydrocarbon solvents such as methylene chloride, 1,2-dichloroethane, and 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; amide solvents such as N,N-dimethylformamide; nitrile solvents such as acetonitrile and propionitrile; aprotic polar solvents such as N-methylpyrrolidone and N,N'-dimethylimidazolinone; and acetic acid. These solvents may be used alone or in combination of two or more as necessary.
Examples of the formylating agent used in the formylation reaction of the hydrazone compound represented by the formula (2) include formic acid, methyl formate, and ethyl formate.
Such a formylating agent can be used in an amount of usually 1 to 100 equivalents, preferably 1 to 10 equivalents, based on the hydrazone derivative represented by the formula (2).
The reaction can usually be carried out within a temperature range of from -78°C to the boiling point of the solvent used, and is preferably carried out at a temperature between 0°C and the boiling point of the solvent.
The reaction time varies depending on the reaction temperature etc. and cannot be generalized, but the reaction is usually completed within 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, such as organic solvent extraction, chromatography, recrystallization, distillation, etc., and can be further purified by a commonly used purification means.

［式中、R₉は、Ｃ_1-6アルキル基を示し、X、Y₁、Y₂、Y₃、Y₄、R₁、R₃、R₄、R₅及びnは、前記式（１）～（２）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、６及び７で示されるものが挙げられる。 Reaction Scheme 4

[In the formula, _R9 represents a _C1-6 alkyl group, and X, _Y1 , _Y2 , _Y3 , _Y4 , _R1 , _R3 , _R4 , _R5 and n are as defined in the formulas (1) and (2).]
Specific embodiments of this reaction scheme 4 include those shown in reaction schemes 5, 6 and 7 below.

［式中、R₁は、水素原子、R₆は、Ｃ_1-6アルキル基を示し、X、Y₁、Y₂、Y₃、Y₄、R₃、R₄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（１０）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（１７）との反応により製造することができる。 Reaction Scheme 5

[In the formula, _R1 is a hydrogen atom, _R6 is a _C1-6 alkyl group, and X, _Y1 , _Y2 , _Y3 , _Y4 , _R3 , _R4 and n are as defined above.]
In the method shown in reaction scheme 5, the hydrazone derivative represented by the formula (10) can be produced by reacting the hydrazone derivative represented by the formula (2) with an orthoformate ester (17).

The solvent used in the reaction between the hydrazone compound represented by formula (2) and the orthoformate represented by formula (17) may be any of a wide variety of known solvents, so long as they are inert to the reaction. Examples of such solvents include aliphatic or alicyclic hydrocarbon solvents such as hexane, cyclohexane, and heptane; aromatic hydrocarbon solvents such as benzene, chlorobenzene, toluene, and xylene; halogenated hydrocarbon solvents such as methylene chloride, 1,2-dichloroethane, and 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; amide solvents such as N,N-dimethylformamide; nitrile solvents such as acetonitrile and propionitrile; aprotic polar solvents such as N-methylpyrrolidone and N,N'-dimethylimidazolinone; and acetic acid. These solvents may be used alone or in combination of two or more as necessary.
Examples of the orthoformate (17) used in the iminization reaction of the hydrazone compound represented by the formula (2) include methyl orthoformate, ethyl orthoformate, propyl orthoformate, and butyl orthoformate.
Such an orthoformate (17) can be used in an amount of usually 1 to 20 equivalents, preferably 2 to 10 equivalents, based on the hydrazone derivative represented by the above formula (2).
The reaction can usually be carried out within a temperature range of from -78°C to the boiling point of the solvent used, and is preferably carried out at a temperature between 0°C and the boiling point of the solvent.
The reaction time varies depending on the reaction temperature etc. and cannot be generalized, but the reaction is usually completed within 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, such as organic solvent extraction, chromatography, recrystallization, distillation, etc., and can be further purified by a commonly used purification means.

［式中、R₇は、水素原子又はＣ_1-6アルキル基を示し、R₈は、水素原子、Ｃ_1-6アルキル基、Ｃ_1-6ハロアルキル基、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Ｃ_1-6アルキル基、Ｃ_1-6アルコキシ基、Ｃ_2-6アルケニル基、Ｃ_2-6ハロアルケニル基、Ｃ_2-6アルキニル基、Ｃ_2-6ハロアルキニル基、Ｃ_3-6シクロアルキル基又は置換されてもよいベンジル基を示し、又は、R₇とR₈とは、それらが結合している窒素原子と一緒になって、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、R₄、R₆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（９）で表されるヒドラゾン誘導体は、前記式（１０）で表されるヒドラゾン誘導体と前記式（１１）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 Scheme 6

[wherein R ₇ represents a hydrogen atom or a C _1-6 alkyl group, R ₈ represents a hydrogen atom, a C _1-6 alkyl group, a C _1-6 haloalkyl group, a hydroxy C _1-6 alkyl group, a C _1-6 alkoxy C _1-6 alkyl group, a C _3-6 cycloalkyl C _1-6 alkyl group, a C _1-6 alkoxy group, a C _2-6 alkenyl group, a C _2-6 haloalkenyl group, a C _2-6 alkynyl group, a C _2-6 haloalkynyl group, a C _3-6 cycloalkyl group or an optionally substituted benzyl group, or R ₇ and R ₈ may together with the nitrogen atom to which they are bonded form a saturated or unsaturated 4- to 7-membered ring. X, Y ₁ , Y ₂ , Y ₃ , Y ₄ , R ₃ , R ₄ , R ₆ and n are as defined above.]
In the method shown in reaction scheme 6, the hydrazone derivative represented by the formula (9) can be produced by reacting the hydrazone derivative represented by the formula (10) with the amine derivative represented by the formula (11).

The solvent used in the amination reaction of the hydrazone compound represented by the formula (10) may be any of a wide variety of known solvents, so long as they are inert to the reaction. Examples of such solvents include aliphatic or alicyclic hydrocarbon solvents such as hexane, cyclohexane, and heptane; aromatic hydrocarbon solvents such as benzene, chlorobenzene, toluene, and xylene; halogenated hydrocarbon solvents such as methylene chloride, 1,2-dichloroethane, and 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; amide solvents such as N,N-dimethylformamide; nitrile solvents such as acetonitrile and propionitrile; aprotic polar solvents such as N-methylpyrrolidone and N,N'-dimethylimidazolinone; and acetic acid. These solvents may be used alone or in combination of two or more as necessary.
The amine derivative (11) can be used in an amount of usually 1 to 5 equivalents, preferably 1 to 2.5 equivalents, based on the hydrazone derivative represented by the formula (10).
The reaction can usually be carried out within a temperature range of from -78°C to the boiling point of the solvent used, and is preferably carried out at a temperature between 0°C and the boiling point of the solvent.
The reaction time varies depending on the reaction temperature etc. and cannot be generalized, but the reaction is usually completed within 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, such as organic solvent extraction, chromatography, recrystallization, distillation, etc., and can be further purified by a commonly used purification means.

［式中、X、Y₁、Y₂、Y₃、Y₄、R₃、R₄、R₆、R₇、R₈及びnは、前記で定義した通りである。］なお、式（７）で表される化合物は、既に説明を行った式（２）におけるR₁が、水素原子である化合物と同じである。
反応式７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（７）で表されるヒドラゾン誘導体とアセタール誘導体（１８）との反応により製造することができる。なお、アセタール誘導体（１８）は、公知の化合物であり、その製造方法も周知であり、市販薬としても入手可能である。 Reaction Scheme 7

[In the formula, X, _Y1 , _Y2 , _Y3 , _Y4 , _R3 , _R4 , _R6 , _R7 , _R8 and n are as defined above.] The compound represented by formula (7) is the same as the compound represented by formula (2) already explained in which _R1 is a hydrogen atom.
In the method shown in reaction scheme 7, the hydrazone derivative represented by formula (9) can be produced by reacting the hydrazone derivative represented by formula (7) with an acetal derivative (18). The acetal derivative (18) is a known compound, and its production method is also well known, and it is also available as a commercial drug.

The solvent used in the reaction between the hydrazone compound represented by formula (7) and the acetal derivative represented by formula (18) may be any of a wide variety of known solvents, so long as they are inert to the reaction. Examples of such solvents include aliphatic or alicyclic hydrocarbon solvents such as hexane, cyclohexane, and heptane; aromatic hydrocarbon solvents such as benzene, chlorobenzene, toluene, and xylene; halogenated hydrocarbon solvents such as methylene chloride, 1,2-dichloroethane, and 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; amide solvents such as N,N-dimethylformamide; nitrile solvents such as acetonitrile and propionitrile; aprotic polar solvents such as N-methylpyrrolidone and N,N'-dimethylimidazolinone; and acetic acid. These solvents may be used alone or in combination of two or more as necessary.
An example of the acetal derivative (18) used in the imino reaction of the hydrazone compound represented by the above formula (7) is N,N-dimethylformamide dimethyl acetal.
The acetal derivative (18) can be used in an amount of usually 1 to 10 equivalents, preferably 1 to 5 equivalents, based on the hydrazone derivative represented by the formula (7).
The reaction can usually be carried out within a temperature range of from -78°C to the boiling point of the solvent used, and is preferably carried out at a temperature between 0°C and the boiling point of the solvent.
The reaction time varies depending on the reaction temperature etc. and cannot be generalized, but the reaction is usually completed within 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, such as organic solvent extraction, chromatography, recrystallization, distillation, etc., and can be further purified by a commonly used purification means.

［式中、Lは、ハロゲン原子や、メタンスルホニルオキシ基、トリフルオロメタンスルホニル基、p-トルエンスルホニルオキシ基等の脱離基を示し、X、Y₁、Y₂、Y₃、Y₄、R₁、R₃、R₄及びnは、前記式（２）で定義した通りである。］
反応式８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（１２）で表されるヒドラゾン誘導体と、前記式（１３）で表されるアルキル化剤とを、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。 Reaction Scheme 8

[In the formula, L represents a leaving group such as a halogen atom, a methanesulfonyloxy group, a trifluoromethanesulfonyl group, or a p-toluenesulfonyloxy group, and X, _Y1 , _Y2 , _Y3 , _Y4 , _R1 , _R3 , _R4 , and n are as defined in the formula (2).]
In the method shown in Reaction Scheme 8, the hydrazone derivative represented by the formula (4) can be produced by reacting the hydrazone derivative represented by the formula (12) with an alkylating agent represented by the formula (13) in the presence or absence of a base in an inert solvent.

The solvent used in the alkylation reaction of the hydrazone derivative represented by the formula (12) may be any of a wide variety of known solvents, so long as they are inert to the reaction. Examples of such solvents include aliphatic or alicyclic hydrocarbon solvents such as hexane, cyclohexane, and heptane; aromatic hydrocarbon solvents such as benzene, chlorobenzene, toluene, and xylene; halogenated hydrocarbon solvents such as methylene chloride, 1,2-dichloroethane, and 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; amide solvents such as N,N-dimethylformamide; nitrile solvents such as acetonitrile and propionitrile; aprotic polar solvents such as N-methylpyrrolidone and N,N'-dimethylimidazolinone; and acetic acid. These solvents may be used alone or in combination of two or more as necessary.
Examples of the alkylating agent (13) used in the alkylation reaction of the hydrazone compound represented by the formula (12) include methyl iodide, ethyl iodide, dimethyl sulfate, and the like.
Such an alkylating agent can be used in an amount of usually 1 to 10 equivalents, preferably 1 to 3 equivalents, based on the hydrazone derivative represented by the formula (12).
The reaction can usually be carried out within a temperature range of from -78°C to the boiling point of the solvent used, and is preferably carried out at a temperature between 0°C and the boiling point of the solvent.
The reaction time varies depending on the reaction temperature etc. and cannot be generalized, but the reaction is usually completed within 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, such as organic solvent extraction, chromatography, recrystallization, distillation, etc., and can be further purified by a commonly used purification means.

Representative compounds of the hydrazone derivatives of the present invention represented by the above formula (1) are shown in Table 1, representative compounds of the hydrazone derivatives of the present invention represented by the above formula (2) are shown in Table 2, and representative compounds of the ketone derivatives of the present invention represented by the above formula (3) are shown in Table 3, but the scope of the present invention is not limited to these compounds.
In Tables 1 to 3, physical properties are indicated as properties or melting points (°C), "i-" indicates iso, "n-" indicates normal, "Me" indicates a methyl group, "Et" indicates an ethyl group, "Pr" indicates a propyl group, *1 indicates that -CH=CH-CH=CH- is bonded to the 3- and 4-positions of the phenyl group, and *2 indicates that -CH=CH-CH=CH- is bonded to the 2- and 3-positions of the phenyl group.

General formula (1)

General formula (2)

General formula (3)

The compound of the present invention can be used for the prevention and extermination of organisms that are harmful in various situations, such as agriculture, indoors or forests, livestock, or hygiene. Specific use situations, target pests, and use methods are shown below, but the content of the present invention is not limited thereto.
The compound of the present invention represented by the formula (1) can be effectively used in agricultural crops, for example, edible crops (rice, barley, wheat, rye, oats, and other wheat, corn, potato, sweet potato, taro, soybean, adzuki bean, broad bean, pea, kidney bean, peanut, and other legumes), vegetables (Brassicaule crops such as cabbage, Chinese cabbage, radish, turnip, broccoli, cauliflower, and komatsuna, pumpkin, cucumber, and other Brassica crops, etc., Cucumbers, watermelons, melons, eggplants, tomatoes, bell peppers, peppers, okra, spinach, lettuce, lotus root, carrots, burdock, garlic, onions, green onions, etc.), mushrooms (shiitake mushrooms, mushrooms, etc.), fruit trees and fruits (apples, citrus fruits, pears, grapes, peaches, plums, cherries, walnuts, chestnuts, almonds, bananas, strawberries, etc.), incense It can also be used to control harmful organisms such as arthropods, mollusks, nematodes, fungi and bacteria of the phylum Eumycota, Myxomycota, Bacteria and Actinomycota that damage ornamental crops (lavender, rosemary, thyme, parsley, pepper, ginger, etc.), specialty crops (tobacco, tea, sugar beet, sugar cane, hops, cotton, hemp, olive, rubber, coffee, etc.), pasture and forage crops (timothy, clover, alfalfa, corn, sorghum, orchard grass, grasses and legumes, etc.), turfgrass (Korean grass, bentgrass, etc.), forest trees (fir trees, spruces, pines, Japanese cypress, cedar, Japanese cypress, etc.) and ornamental plants (herbaceous plants and flowers such as chrysanthemums, roses, carnations, orchids, ginkgo trees, cherry trees, Japanese laurels, etc.). Specific harmful organisms include the following:

Lepidoptera of the class Insecta of the phylum Arthropoda, for example, Helicoverpa armigera, Heliothis spp., Agrotis segetum, Autographa nigrisigna, Trichoplusia ni, Mamestra brassicae, Spodoptera exigua, Spodoptera litura, etc. of the family Noctuidae, Plutella xylostella, etc. of the family Tortricidae, Adoxophyes orana fasciata, Adoxophyes honmai, Archips fuscocupreanus, Homona magnanima, Caloptilia theivora, Grapholita molesta, etc., Eumeta minuscula, etc., Lyonetia prunifoliella malinella, Lyonetia clerkella, etc., Phyllocnistis citrella, etc., Phyllonorycter ringoniella, etc., Acrolepiopsis sapporensis, etc., Synanthedin hector, etc., Stathmopoda masinissa, etc., Pectinophora gossypiella, etc., Carposina niponensis, etc., Cossus jezoensis, etc., Nemapogon granella, etc., Monema flavecens, Parasa lepida, Scopelodes contracus, etc., Chilo suppressalis, Scirpophaga incertulas, Cnaphalocrocis medinalis, Hellulla undalis, Conogethes punctiferlis, Diaphania indica, Parapediasia teterrella, etc., Locastra muscosalis, etc., Parnara guttata, etc., Papilio xuthus, etc., Pieridae, Pieris rapae crucivora, etc., Lampides boeticus, etc., Ascotis selenaria, etc., Agrius convolvuli, etc., Phalera flavescens, etc., Malacosoma neustrium testaceum, etc., Saturnidae, Saturnidae, Euproctis japonica, etc., Adults, larvae and eggs of the following moths: Orgyia pseudoconspersa, Orgyia thyellina, Telochurus recens approximans, etc.; Spilosoma imparilis, Hyphantria cunea, etc. of the Arctiidae family; Grapeberry Moth (Endopiza viteana), Codling Moth (Laspeyresia pomonella), etc.;

Coleoptera, for example, Scarabaeidae (Anomala cuprea), Japanese beetle (Popillia japonica), Japanese flower beetle (Oxycetonia jucunda), cherry beetle (Anomala geniculata), etc.; Buprestidae (Agrilus auriventris), etc.; Elateridae (Melanotus fortnumi), etc.; Ladybird beetle (Epilachna vigintioctopunctata), etc.; Cerambycidae (Anoplophora malasiaca), grape tiger beetle (Xylotrechus pyrrhoderus), etc.; Chrysomelidae (Aulacophora femoralis), rootworm species (Diabrotica spp.), Phyllotreta striolata, Cassida nebulosa, Phaedon brassicae, Oulema oryzae, Epilachna varivestis, Leptinotarsa decemlineata, Rhynchites heros, Cylas formicarius, Curculionidae, Curculionidae, Lissorhoptrus oryzophilus, Anthonomus gradis grandis, Sphenophrus venatus vestitus) and adults, larvae and eggs of the Nitidulidae family, such as Epuraea domina;

Heteroptera of the order Hemiptera, for example, Eurydema rugosum, Eysarcoris lewisi, Eysarcoris parvus, Nezara viridula, Plautia stali, Halymorpha mista, etc. of the family Hemiptera, Urochela luteovoria, etc. of the family Lygaeidae, Togo hemipterus, etc. of the family Hemiptera, Riptortus clavatus, Cletus punctiger, etc., spider bug (Leptocorisa chinensis) of the family Heteroptera, red spotted bug (Dysdeercus cingulatus) of the family Pyrrhocoridae, Stephanitis nashi, Stephanitis pyrioides of the family Tingidae, Apolygus spinolai, Stenotus rubrovittalus, Trigonotylus coelestialium of the family Miridae, Megacopta punctatissimum of the family Heteroptera, etc., adults, larvae and eggs;

Hemiptera, Homoptera, for example, Platypleura kaempferi, etc., Cicadidae, Arboridia apicalis, Empoasca onukii, Nephotettix cincticeps, Nephotettix virescens, etc., Delphacidae, Laodelphax striatellus, Nilaparvata lugens, Sogatella furcifera, etc., Geisha distinctissima, etc., Psylla psylla, etc., pyrisuga), Diaphorina citri, etc., Aleurocanthus spiniferus, Bemisia argentifolii, various biotypes of Bemisia tabaci, Dialeurodes citri, Trialeurodes vaporariorum, etc., Viteus vitifolii, etc., Aphididae, Aphis citricola, Aphis craccivora, Aphis gossypii, Aulacorthum solani, Brevicoryne brassicae), Toxoptera aurantii, Toxoptera citricidus, Aulacorthum magnoliae, Schizaphis piricola, Nippolachnus piri, Lipaphis erysimi, Hyalopterus pruni, Pleotrichophorus chrysanthemi, Macrosiphoniella sanborni, Megoura crassicauda, Sitobion ibarae, Macrosiphum euphorbiae, Myzus scaly aphid varians, Myzus persicae, Rhopalosiphum rufiabdominalis, Rhopalosiphum padi, Sitobion akebiae, Eriosoma lanigerum, etc., Icerya purchasi, etc., Pseudococcidae, Pseudococcus comstocki, Phenacoccus viburnae, Phenacoccus kraunhiae, etc., Ceroplastes ceriferus, Ceroplastes rostrata ... rubens), and adults, larvae and eggs of the scale insect family Aonidiella aurantii, pear scale insect Comstockaspis perniciosa, mulberry scale insect Pseudaulacaspis pentagoa, Yanonensis scale insect Unaspis yanonensis, etc.;

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

Hymenoptera, for example, Athalia rosae ruficornis, Arge pagana, etc., Arge mali, etc., Dryocsmus kuriphilus, etc., Megachile nipponica nipponica, etc., Formicidae, Formica japonica, Camponotus kiusiuensis, Lasius fuliginosus, Solenopsis richteri, S. invicta, S. geminata, etc., adults, larvae and eggs;
Diptera, for example, Asphondylia yushimai (Cicada midge), Rhacochlaena japonica (Sweet fruit fly), Bactrocera cucurbitae (Melidae), Hydrellia griseola (Rice fly), Drosophila suzukii (Drosophilidae), Liriomyza trifolii (Bean leafminer), Liriomyza sativae (Tomato leafminer), Chromatomyia horticola (Rice leafminer), Agromyza oryzae (Rice leafminer), Liriomyza bryoniae (Eggplant leafminer), Delia cephalosporum (Sedum) (Anthomyidae), platura), onion fly (Delia antiqua), etc.;

Orthoptera, for example, Locusta migratoria of the grasshoppers family, Ruspolia lineosa of the grasshoppers family, Teleogryllus emma of the cricket family, Truljalia hibinonis of the field cricket family, Gryllotalpa orientalis of the grasshopper family, Oxya yezoensis of the grasshopper family, and other adults, larvae and eggs;
Isoptera, for example, adults, larvae and eggs of Odontotermes formosanus of the Termitidae family;
Dermaptera, for example, adults, larvae and eggs of Labidura riparia of the Dermaptera family;

Collembola of the class Insecta of the phylum Arthropoda, for example, adults, larvae and eggs of Sminthurus viridis of the family Collembola, Onychiurus matsumotoi of the family Onychiurus; Isopada of the class Malacostraca of the phylum Arthropoda, for example, adults, larvae and eggs of Armadillidium vulgare of the family Armadillididae;
Arthropoda, Arachnida, Acari, for example, Polyphagotarsonemus latus, Phytonemus pallidus, etc., Penthaleus major, etc., Dermestidae, Brevipalpus lewisi, Brevipalpus phoenicis, etc., Tetranychus citri, Panonychus ulmi, Tetranychus urticae, Tetranychus kanzawai, Amphitetranychus viennensis, Oligonychus ununguis, Bryobia nigricans, etc., eharai), Miyake spider mite (Eotetranychus kankitus), clover spider mite (Bryobia praetiosa), etc., apple rust mite (Aculus Schlechtendali), citrus rust mite (Aculops pelekassi), Ryukyu citrus rust mite (Phyllocoptruta citri), false pear rust mite (Eriophyes chibaensis), tulip rust mite (Aceria tulipae), grape leafminer mite (Colomerus vitis), peach rust mite (Aculus fockeui), tea rust mite (Calacarus carinatus), etc., Acaridae, such as Tyrophagus putrescentiae, Robin mite (Rhizoglyphus robini) adults, larvae and eggs;

Architaenioglossa, Gastropoda, Mollusca, e.g. Pomacea canaliculata, Plumonata, Achatina fulica, Meghimatium bilineatum, Milax gagates, Lehmannina valentiana, Acusta despecta sieboldiana, Acusta despecta sieboldiana, Plumonata, Achatina fulica, Meghimatium bilineatum, Milax gagates, Lehmannina valentiana, Acusta despecta sieboldiana, Plumonata, Achatina fulica, Meghimatium bilineatum ...
Order Tylenchida of the phylum Nematoda, for example, Ditylenchus destructor of the Anguinidae family, Tylenchorhynchus claytoni of the Tylencorhynchidae family, Pratylenchus penetrans and Pratylenchus coffeae of the Pratylenchiidae family, Helicotylenchus dihystera of the Hoplolymidae family, Globodera rostochiensis of the Heterodera family, Meloidogyne incognita of the Meloidogyne family, Criconema jaejuense of the Criconema family, Nothotylenchus acris, etc., Aphelecchoides fragarriae, etc., of the Aphelenchoides family; Doriraimus order of the Urygonia class, for example, Xiphinema sp. of the Longidoridae family, Trichodorus sp., etc., of the Trichodoridae family;
Fungi and bacteria such as Eumycota, Myxomycota, Bacteriomycota, and Actinomycota.

Specific examples of diseases to which the compound of the present invention represented by the formula (1) can be applied include rice blast disease (Pyricularia oryzae), brown spot disease (Cochliobolus miyabeanus), sheath blight disease (Rhizoctonia solani), inner lemma browning disease (Pantoea ananatis), brown stripe disease (Acidovorax avene subsp. avenae), leaf sheath browning disease (Pseudomonas fuscovaginae), white leaf blight disease (Xanthomonas oryzae pv. oryzae), bacterial blight disease (Burkholderia plantarii), etc.; wheat powdery mildew (Erysiphe graminis), red mold disease (Gibberella zeae), red rust disease (Puccinia striiformis, P. graminis, P. recondita, P. hordei), snow mold disease (Typhula sp., Micronectriella nivalis), naked smut (Ustilago tritici, U. nuda), cattle smut (Tilletia caries), eyespot disease (Pseudocercosporella herpotrichoides), scald (Rhynchosporium secalis), leaf blight (Septoria tritici), smut blight (Leptosphaeria nodorum), net spot disease (Pyrenophora teres), hail disease (Helminthosporium zonatum Ikata), black node disease (Pseudomonas syringae pv. japonica), etc.; citrus black spot disease (Diaporthe citri), scab disease (Elsinoe fawcetti), fruit rot disease (Penicillium digitatum, P. italicum), brown rot disease (Phytophthora citrophthora,, P. nicotianae), black spot disease (Phyllosticta citricarpa) etc.;

Apple Monilinia mali, canker disease, powdery mildew, Alternaria mali, black spot, Venturia inaequalis, black spot, Mycospherella pomi, anthracnose, Botryosphaeria berengeriana, red spot, Monilinia fructicola, etc.; Pear Venturia nashicola, V. pirina, black spot, Alternaria kikuchiana, red spot, Monilinia haraeanum, brown spot, Monilinia fructigena, etc.; Peach Monilinia fructicola, black spot, Cladosporium carpophilum, Phomopsis rot (Phomopsis sp.), perforation bacterial disease (Brenneria nigrifluens), etc.; Grape black rot (Elsinoe ampelina), late rot (Colletotrichum acutatum), powdery mildew (Uncinula necator), rust (Phakopsora ampelopsidis), black rot (Guignardia bidwellii), downy mildew (Plasmopara viticola), gray spot (Monilinia fructigena), black spot (Cladosporium viticolum), gray mold (Botrytis cinerea), crown rot bacterial disease (Agrobacterium vitis), etc.; Persimmon anthracnose (Gloeosporium kaki), leaf drop disease (Cercospora kaki, Mycoshaerella nawae), etc.; Cucurbit anthracnose (Colletotrichum lagenarium), powdery mildew (Sphaerotheca fuliginea, Oidiopsis taurica), vine wilt (Didymella bryoniae), vine splitting disease (Fusarium oxysporum), downy mildew (Pseudoperonospora cubensis), late blight (Phytophthora sp.), seedling damping-off disease (Pythium sp.), etc.; cucumber bacterial spot disease (Pseudomonas syringae pv. lochrymans), edge blight disease (Pseudomonas viridiflava), brown spot bacterial disease (Xanthomonas campestris pv. cucurbitae), etc.; melon bacterial brown spot disease (Xanthomonas campestris pv. cucurbitae), hairy root disease (Agrobacterium rhizogens), canker disease (Streptomyces sp.), etc.; watermelon bacterial fruit spot disease (Acidovorax avenae pv. citrulli), etc.; Solanaceae vegetable bacterial wilt (Ralstonia solanacearum), etc.;

Tomatoes: ring spot disease (Alternaria solani), leaf mold disease (Cladosporium fulvum), late blight (Phytophthora infestans), canker disease (Clavibacter michiganense subsp. michiganense), stem necrosis disease (Pseudomonas corrugata), soft rot disease (Pectobacterium carotovorum subsp. carotovorum), etc.; eggplants: brown spot disease (Phomopsis vexans), powdery mildew (Erysiphe cichoracearum), etc.; cruciferous vegetables: black spot disease (Alternaria japonica), white spot disease (Cercosporella brassicae), soft rot disease (Pectobacterium carotovorum subsp. carotovorum), etc.; cabbage: rot disease (Pseudomonas syringae pv. marginalis), black rot disease (Xanthomonas campestris pv. campestris), etc.; lettuce rot (Pseudomonas cichorii, Pseudomonas viridiflava), bacterial spot disease (Xanthomonas campestris pv. vitians), onion rust (Puccinia allii), etc.; soybean purple spot (Cercospora kikuchii), black rot (Elsinoe glycines), black spot disease (Diaporthe phaseolorum var. sojae), etc.; kidney bean anthracnose (Colletotrichum lindemthianum), etc.; peanut black spot disease (Cercospora personata), brown spot disease (Cercospora arachidicola), etc.; pea powdery mildew (Erysiphe pisi), etc.; potato summer blight (Alternaria solani), blight (Phytophthora infestans), leaf rot disease fungus (Rhizoctonia solani), etc.; strawberry powdery mildew (Sphaerotheca humuli), etc.; tea net blight (Exobasidium reticulatum), white spot (Elsinoe leucospila), red burn (Pseudomonas syringae pv. theae), canker (Xanthomonas campestris pv. theicola), etc.; tobacco red spot (Alternaria longipes), powdery mildew (Erysiphe cichoracearum), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacina), late blight (Phytophthora nicotianae), damping-off (Ralstonia solanacearum), hollow disease (Pectobacterium carotovorum subsp. carotovorum), etc.; sugar beet brown spot (Cercospora beticola), seedling damping-off (Aphanomyces cochliodes, etc.; rose black spot (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa), etc.; chrysanthemum brown spot (Septoria chrysanthemi-indici), white rust (Puccinia horiana), crown gall (Agrobacterium tumefaciens), etc.; eggplant, cucumber, lettuce, etc. gray mold (Botrytis cinerea), sclerotinia sclerotiorum; turf snow mold (Pythium iwayamai, Tyohula incarnate, Fusarium nivale, Sclerotinia borealis), powdery mildew (Erysiphe graminis), fary ring disease (Lycoperdon perlatum, Lepista subnudo, Marasmius oreades), pseudo-leaf rot (Ceratobasidium spp.), damping-off (Gaemannomyces graminis), Curvularia leaf blight (Curvularia geniculata), leaf rot (Rhizoctonia solani), Pythium wilt (Pythium periplocum, Pythium vanterpoolii), rust (Puccinia spp.), dollar spot (Sclerotinia homoeocarpa), etc.; bentgrass red burn (Pythium aphanidermatum), anthracnose (Colletotrichum sp.).

The compound of the present invention represented by the formula (1) can be used to control arthropods and fungi that are active inside buildings, including ordinary houses, and that damage or rot wood and wood products such as wooden furniture, stored food, clothing, books, etc., thereby causing damage to our lives. Specific examples of harmful organisms include the following:

Arthropoda, Insecta, Termitidae, for example, Coptotermes formosanus, Reticulitermes speratus, other Reticulitermes hesperus, R. tibialis, R. flavipes, R. lucifugus, R. santonensis, etc., Incisitermes minor, Odontotermes formosanus, Hodotermopsis jzponica, Cryptotermes domesticus, adults, larvae and eggs;
Coleoptera, for example, the family Curculionidae, such as the rice weevil Sitophilus zeamais and the rice weevil Sitophilus zeamais; the family Bruchidae, such as the azuki bean weevil Callosobruchus chinensis, the pea weevil Bruchus pisorum and the broad bean weevil Bruchus rufimanus; the family Tenebrionidae, such as the red flour beetle Tribolium castaneum and the flat-headed red flour beetle Tribolium confusum; the family Oryzaephilus surinamensis and the short-horned flat beetle Cryptolestes pusillus; the family Anobiidae, such as the cigarette beetle Lasioderma serricorne and the cigarette beetle Stegobium paniceum), etc., Attagenus unicolor japonicus, Anthrenus verbasci, Dermestes maculatus, etc., Gibbium aequinnoctiale, etc., Dinoderus minutus, Rhizopertha dominica, etc., Lyctus brunneus, etc., adults, larvae and eggs, etc., of the Lyctidae family;

Lepidoptera, for example, adults, larvae and eggs of Cadra cautella, Ephestia kuehniella, Plodia interpunctella, etc. of the Pyralidae family, Sitotroga cerealella, etc. of the Gelechiidae family, Tinea translucens, Tineola bisselliella, etc. of the Tineidae family; Psocotyledonidae, for example, adults, larvae and eggs of Lepinotus reticulatus, etc. of the Liposcelididae family, Liposcelis bostrychophilus, etc. of the Liposcelididae family:
Blattidae, such as the German cockroach (Blattella germanica) of the family Blattidae, the cockroach (Periplaneta fuliginosa) of the family Blattidae, the cockroach (Periplaneta japonica) of the family Blattidae, etc.; Hymenoptera, such as the Formicidae, the house ant (Monomorium pharaoni) of the family Formicidae, the house ant (Monomorium nipponense) of the family Formicidae, etc., the adults, larvae and eggs;

Thymidia, for example, adults, larvae and eggs of Ctenolepisma villosa, Lepisma saccharina and the like of the family Thimpinae;
Diptera, for example, adults, larvae and eggs of the Drosophilidae family, such as Drosophila melangogaster, and the Cheese Fly family, such as Piophila casei;
Arthropoda, Arachnida, Acarina, for example, Tyrophagus putrescentiae, Lardoglyphus konoi, Carpoglyphus lactis, and other adults, larvae, and eggs;
Fungal wood-decay fungi such as Tyromyces palustris and Coriolus versicolor;
Microorganisms that cause material degradation include Aspergillus niger, Aspergillus terreus, Aureobasidium pullulans, Chaetomium globosum, Cladosporium cladosporioides, Eurotium tonophilus, Fusarium moniliforme, Gliocladium virens, Myrothecium verrucaria, Penicillium citrinum, Penicillium funiculosum, Rhizopus oryzae, etc.

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

Arthropoda, Insecta, Lepidoptera, for example, Lymantria dispar, Calliteara argentata, Euproctis pseudoconspersa, Orygia recens approximans, Euproctis subflava, Lymantria dispar, Malacosoma neustria testacea, Dendrolimus spectabilis, Dendrolimus superans, Pyralidae, Crytoblabes loxiella, Agrotis segetum, Tortricidae, Ptycholoma lecheana circumclusana, Cydia kurokoi, Cydia cryptomeriae, etc., Spilosoma imparilis, Hyphantria cunea, etc., Stigmella castanopsiella, etc., Parasa lepida, Scopelodes contracus, Microleon longipalpis, etc., adults, larvae and eggs, etc., of the Scarabaeidae family; Anomala rufocuprea, Heptophylla picea, etc., of the Buprestidae family; Agrilus spinipennis, etc., of the Cerambycidae family; Monochamus alternatus, etc., of the Chrysomelidae family; Basilepta pallidula), etc., Curculionidae: Scepticus griseus, Pine spotted weevil (Shirahoshizo insidiosus), etc., Curculionidae: Giant weevil (Sipalinus gigas), etc., Scolytidae: Pine bark beetle (Tomicus piniperda), Itaya bark beetle (Indocryphalus aceris), etc., Bostrichidae: Rhizopertha dominica, etc., adults, larvae and eggs;

Hemiptera, for example, adults, larvae and eggs of Cinara todocola of the Aphididae family, Adelges japonicus of the Aphididae family, Aspidiotus cryptomeriae of the Diaspididae family, Ceroplastes ceriferus of the Coccidae family, etc.
Hymenoptera, such as adults, larvae and eggs of Pachynematus itoi, Neodiprion sertifer, Dryocosmus kuriohilus, etc., from the Sawfly family; Diptera, such as Tipula aino, Strobilomyia laricicola, Contarinia inouyei, Contarinia matsusintome, etc., from the Cecidomyiidae family;
Arthropoda, Arachnida, Acari, for example, adults, larvae and eggs of Oligonichus hondoensis, Oligonichus ununguis and the like;
Phylum Nematoda, Class Phantomthia, Order Tylenchidae, for example, Bursaphelenchus xylophilus of the family Parasitaphelenchidae.

The compound of the present invention represented by the formula (1) can also be used to control arthropods, nematodes, trematodes, cestodes, and protozoa that parasitize internally or externally on vertebrates, particularly warm-blooded vertebrates such as livestock and pets, such as cows, sheep, goats, horses, pigs, poultry, dogs, cats, and fish. Target animal species include, in addition to those mentioned above, rodents such as mice, rats, hamsters, and squirrels, carnivores such as ferrets, and pet birds such as ducks and pigeons, as well as laboratory animals. Specific examples of harmful organisms include the following:

Arthropoda, Insecta, Diptera, for example, Tabanus rufidens, Tabanus chrysurus, etc., Musca bezzii, Musca domestica, Stomoxys calcitrans, etc., Gasterophilus intestinalis, etc., Hypoderma bovis, etc., Oestrus ovis, etc., Aldrichina grahami, etc., Phoridae, Megaselia spiracularis, etc., Sepsis punctum, etc., Telmatoscopus spp., etc., albipunctatus), Psychoda alternata, etc., Culex pipiens molestus, Culex pipiens pallens, Anopheles sinensis, Culex pipiens triaeniorhynchus summorosus, Ades albopictus, etc., Simulium iwatense, Prosimulium yezoense, etc., Culicidae Culicidae Culicoides schulzei, Culicoides arakawae, etc., adults, larvae and eggs;
from the order Siphonaptera, for example adults, larvae and eggs of the family Pulexidae, such as cat fleas (Pulex irritans) and dog fleas (Ctenocephalides canis);

Adults, larvae and eggs of the order Phthiraptera, for example, Haematopinidae suis, Haematopinidae eurysternus, etc., Damalinia bovis, etc., Linognathus vituli, etc., and Menopon gallinae, etc.;
Arthropoda, Arachnida, Acarina, e.g., Varroa jacobsoni, Haemaphysalis longicornis, Ixodes ovatus, Boophilus microplus, Amblyomma testudinarium, etc., Ornithonyssus sylvialum, etc., Dermanyssus gallinae, etc., Demodex phylloides, etc., Sarcoptes scabiei bovis, Knemidocoptes mutans, etc., Otodectes malvaceae, etc., Adults, larvae and eggs of Psoroptes communis, etc.;
Strongyleia order of the class Dilinearis of the phylum Nematoda, for example, bovine hookworm, porcine kidneyworm, porcine lungworm, trichostrongylus stercoralis, bovine intestinal nodule worm, etc.:
Ascarids, such as Ascaris suum, Ascaris chicken, etc.;
Platyhelminthes, Trematoda, for example, Schistosoma japonicum, Schistosoma hepatica, Paragonimus deer, Paragonimus westermani, Paragonimus japonicus, etc.;
Cestodes, e.g., Laminaria laminata, Dilated Tapeworm, Beneden's Tapeworm, Quadratus nigricans, Sclera nigricans, Ring Tapeworm, etc.:
Protozoa, Rhizoflagellates, e.g., Histomonas, Promastigote, e.g., Leishmania, Trypanosoma, Multiflagellates, e.g., Giardia, Trichomonads, e.g., Trichomonas:
the order Amoebae of the class Sarcocida, for example, Entamoeba, etc.;
Piroplasma subclass of Sporozoa, for example, Theilaria, Babesia, etc.; Otosporozoa subclass, for example, Eimeria, Plasmodium, Toxoplasma, etc.

The compound of the present invention represented by the formula (1) can be used to eliminate pests that directly harm or cause discomfort to the human body, or to maintain public health against pests that carry or transmit pathogens. Specific pests include the following:

Adults, larvae and eggs of the order Lepidoptera of the phylum Arthropoda, for example, Sphrageidus similis of the family Lymantriidae, Kunugi Kareha of the family Lasiocampidae, Parasa consocia of the family Limacodidae, Artona martini of the family Zygathidae;
Coleoptera, for example, adults, larvae and eggs of Xanthochroa waterhousei of the Cerambycidae family, Epicauta gorhani of the Meloidae family, Paederus fuscipes of the Staphylinidae family, etc.
Hymenoptera, for example, adults, larvae and eggs of Vespa simillima xanthoptera of the Vespidae family, Brachyponera chinensis of the Formicidae family, Batozonellus annulatus of the Bacchus family, etc.;
Diptera, for example, adults, larvae and eggs of Armigeres subalbatus of Culicidae, Culicoides nipponensis of Ceratopogonidae, Chironomus yoshimatsui of Chironomidae, Simulium nikkoense of Simuliidae, Hirosia humilis of Tabanidae, Musca domestica of Muscaidae, Fannia canicularis of Muscidae, Phormia regina of Blowflies, Sarcophaga peregrina of Fleshflies;
from the order Siphonaptera, for example adults, larvae and eggs of the family Pulexidae, such as the human flea (Pulex irritans);
Blattidae, for example, adults, larvae and eggs of the German cockroach (Blattella germanica) of the Blattidae family, the American cockroach (Periplaneta americana), the Smoky brown cockroach (Periplaneta fuliginosa), the Japanese cockroach (Periplaneta japonica) of the Blattidae family, etc.;
Orthoptera, for example, adults, larvae and eggs of Diestrammena japonica and Diestrammena apicalis of the family Orthoptera;
Adults, larvae and eggs of the order Phthiraptera, such as head lice (Pediculus humanus humanus) of the family Pedicidae, and pubic lice (Phthirius pubis) of the family Phthiriidae;
Hemiptera, for example, Cimex lectularius of the family Cimexidae, adults, larvae and eggs of Isyndus obscurus of the family Assassin Bug;

Adults, larvae and eggs of the Collembola order of the Arthropoda phylum, such as Hypogastrura communis of the Collembola family;
Arthropoda, Arachnida, Acarina, for example, Ixodes persulcatus, Ornithonyssus bacoti, Chelacaropsis moorei, Pyemotes ventricosus, Demodex folliculorum, Dermotophagoides pteronyssinus, Sarcoptes scabiei, Trombicula akamushi ...
Araneae, for example, Chiracanthium japonicum of the family of spiders, Heteropoda venatoria of the family of spiders, Spermophora senoculata and Pholcus phalangioides of the family of ghost spiders, Uroctea compactilis of the family of spiders, Plexippus paykulli and Plexippus adansoni of the family of jumping spiders, adults, larvae and eggs;
Scorpionidae, for example, adults, larvae and eggs of the spotted scorpion (Isometrus europaeus) of the family Isometruidae;
Arthropoda, Chelipeda, Scolopendra subspinipes mutilans, Scolopendra subspinipes japonica, and other adults, larvae, and eggs;
The order Centropods, for example, adults, larvae and eggs of the family Centropodidae (Thereuronema hilgendofi);
Arthropoda, Diplopoda, Oxididae, adults, larvae and eggs such as Oxidus gracilis;
Arthropoda, Crustacea, Isopoda, for example, adults, larvae and eggs of Porcellio scaber of the family Isopoda;
The order Gnathids of the class Turphidae of the phylum Annelida, for example, the land leech (Haemadipsa zeylanica japonica) of the family Leech;
Examples of such fungi include tinea fungi such as Trichophyton rubrum and Trichophyton mentagrophytes, candida fungi such as Candida albicans, and aspergillus fungi such as Aspergillus fumigatus, gram-negative bacteria such as Escherichia coli and Pseudomonas aeruginosa, and gram-positive bacteria such as Staphylococcus aureus.

The compounds of the present invention represented by the formula (1) are particularly valuable for controlling pests, such as arthropods, gastropods, nematodes, and fungi, that damage agricultural crops, natural forests, artificial forests, and trees and ornamental plants in urban green spaces. In such situations, the compounds of the present invention can also be present in their commercially useful formulations and the use forms prepared by these formulations as mixtures with other active compounds, such as insecticides, acaricides, nematicides, fungicides, synergists, plant regulators, poison baits, or herbicides.
The form of use may be a flowable agent such as a wettable powder, a granular wettable powder, a dry flowable agent, a water-soluble agent, an emulsion, a liquid agent, an oil agent, an aqueous suspension agent, an aqueous emulsion agent, a capsule agent, a powder agent, a granular agent, a fine granular agent, a bait, a tablet agent, a spray agent, a mist agent, an aerosol agent, etc. In order to obtain these dosage forms, various pesticide adjuvants that have been conventionally used in the technical field of agricultural and horticultural agents can be appropriately used. Such pesticide adjuvants can be used, for example, for the purpose of improving the effect, stabilizing, and improving the dispersibility of agricultural and horticultural agents.

Examples of agricultural chemical adjuvants include carriers (diluents), emulsifiers, wetting agents, dispersants, disintegrants, etc. Examples of liquid carriers include water, aromatic hydrocarbons such as toluene and xylene, alcohols such as methanol, butanol, and glycol, ketones such as acetone, amides such as dimethylformamide, sulfoxides such as dimethylsulfoxide, methylnaphthalene, cyclohexane, animal and vegetable oils, and fatty acids. Examples of solid carriers include clay, kaolin, talc, diatomaceous earth, silica, calcium carbonate, montmorillonite, bentonite, feldspar, quartz, alumina, sawdust, nitrocellulose, starch, and gum arabic.
As the emulsifier or dispersant, a conventional surfactant can be used. For example, anionic surfactants such as higher alcohol sodium sulfate, stearyl trimethyl ammonium chloride, polyoxyethylene alkyl phenyl ether, and lauryl betaine, cationic surfactants, nonionic surfactants, and amphoteric surfactants can be used.
In addition, wetting agents such as dialkyl sulfosuccinate; fixing agents such as carboxymethyl cellulose and polyvinyl alcohol; disintegrants such as sodium lignin sulfonate and sodium lauryl sulfate, etc. can be used.
Of course, the compound of the present invention can be formulated as an active ingredient in one or more combinations. 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 0.5 to 90% by mass, and may be appropriately determined depending on various conditions such as the formulation form and application method. For example, the powder can be prepared to contain about 0.5 to 20% by mass, preferably 1 to 10% by mass, the wettable powder can be prepared to contain about 1 to 90% by mass, preferably 10 to 80% by mass, and the emulsifiable concentrate can be prepared to contain about 1 to 90% by mass, preferably 10 to 40% by mass of the active ingredient.

To control arthropods, gastropods, nematodes, and fungi, the agent is usually sprayed on the stems and leaves of plants in areas where damage caused by these pests has occurred or where damage may occur. In addition, the agent can be applied to soil and absorbed through the roots by mixing into the entire soil layer, applying in rows, mixing into bed soil, treating cell seedlings, treating in planting holes, treating the base of plants, top dressing, treating rice in boxes, applying to the water surface, etc. In addition, the agent can be used for seed treatment such as soaking seeds in the agent, seed dressing, treating with Calper, applying to nutrient solutions in nutrient solution (hydroponic) cultivation, smoking, or injecting into tree trunks. When used, the amount of active ingredient is generally 0.1 to 1000 g, preferably 1 to 100 g, per 10 ares, although this varies depending on the type and amount of pests, the type and cultivation form and growth state of the target crops and trees. To apply this, in the case of flowable formulations such as wettable powders, wettable granules, dry flowable formulations, water-soluble powders, emulsions, liquid formulations, water suspensions/water emulsions, or capsule formulations, it is sufficient to dilute them with water and spray them on crops etc. at an application rate of generally 10 to 1,000 liters per 10 ares, although this varies depending on the type of plant, cultivation form, and growth conditions. In addition, in the case of dusts, sprays, or aerosol formulations, they can be applied to crops etc. in that formulation state.
Examples of application methods when the target pest mainly damages plants in the soil or when the agent is absorbed through the roots to control the target pest include applying the formulation, with or without dilution, to the base of the plant or a seedbed for raising seedlings, etc., diluting the formulation with or without dilution in water, spraying granules at the base of the plant or a seedbed for raising seedlings, spraying dust, wettable powder, water dispersible granules, granules, etc. before sowing or transplanting and mixing with the entire soil, and spraying dust, wettable powder, water dispersible granules, granules, fine granules, etc. in planting holes, rows, etc. before sowing or planting the plant. For wettable powders, granular wettable powders, water-soluble powders, emulsifiable concentrates, liquid preparations, water suspensions, water emulsions, and other flowable preparations, capsule preparations, etc., they are diluted with water and generally applied at a rate of 5 to 500 liters per 10 ares, and sprayed or irrigated on the soil surface so as to cover the entire area to be treated evenly. For powders, granules, fine granules, baits, etc., they are sprayed on the soil surface in their formulations so as to cover the entire area to be treated evenly. Spraying or irrigation may be performed around seeds, crops, or trees that you wish to protect from damage. The active ingredients may also be mechanically dispersed by tilling during or after spraying.

As for the method of application to rice seedling boxes, the formulation may vary depending on the application time, such as application at the time of sowing, application during the greening period, application at the time of transplanting, etc., and may be applied in the form of, for example, a dust, water dispersible granule, granule, fine granule, etc. Application can also be performed by mixing with culture soil, and the culture soil can be mixed with a dust, water dispersible granule, granule, or fine granule, for example, by mixing with bed soil, covering soil, or the entire culture soil. Alternatively, the culture soil and various formulations may simply be applied in alternating layers.
For application to paddy fields, solid preparations such as jumbo formulations, pack formulations, granules, and granular water dispersible agents, and liquid preparations such as flowables and emulsions are usually sprayed on flooded paddy fields. In addition, at the time of rice planting, appropriate preparations can be sprayed or injected directly or mixed with fertilizers into the soil. In addition, by using liquids such as emulsions and flowables at the water inlet or irrigation equipment, it is possible to apply them labor-savingly along with the water supply.
Examples of seed treatment methods include a method in which seeds are soaked in a liquid or solid formulation, diluted or undiluted, to adhere or penetrate the agent, a method in which a solid or liquid formulation is mixed with seeds and powder-coated to adhere to the surface of the seeds, a method in which the formulation is mixed with an adhesive carrier such as a resin or polymer and then coated on the seeds, a method in which the formulation is sprayed around the seeds at the same time as planting, etc. The "seed" to be subjected to the seed treatment means a plant body in the early stage of cultivation used for plant propagation, and examples thereof include seeds, as well as bulbs, tubers, seed potatoes, sprouts, bulbils, bulbs, or plant bodies for vegetative propagation for cultivation by cuttings. In addition, the term "soil" or "cultivation carrier" for plants in the case of application refers to a support for cultivating crops, particularly a support for growing roots, and the material is not particularly limited as long as it is a material in which plants can grow, and may be so-called soil, seedling mat, water, etc., and specific materials include, for example, sand, pumice, vermiculite, diatomaceous earth, agar, gel-like substances, polymeric substances, rock wool, glass wool, wood chips, bark, etc.
For the sowing of cultivated plants to be transplanted or the treatment during the seedling raising stage, in addition to direct treatment of the seeds, it is preferable to irrigate the seedling bed with a liquid agent or to spray the granules. It is also preferable to apply the granules to the planting hole at the time of planting or to mix the granules in the cultivation carrier near the transplanting site.

The compound of the present invention represented by the formula (1) is also valuable for protecting wood (standing trees, fallen trees, processed wood, stored wood, or structural wood) from damage by insects such as termites or coleoptera, fungi, and the like. In such a case, it can be controlled by spraying, injecting, irrigating, or applying an oil solution, emulsion, wettable powder, or sol, or by spraying a powder or granule, etc., on the wood or the soil around it. In addition, the oil solution, emulsion, wettable powder, or powder used in this case can be present as a mixture with other active compounds, such as insecticides, acaricides, nematicides, fungicides, repellents, synergists, etc., and these formulations can contain the active ingredient compound in a total amount of 0.0001 to 95% by mass, preferably 0.005 to 10% by mass for oil solutions, dusts, and granules, and 0.01 to 50% by mass for emulsions, wettable powders, and sols. When controlling arthropods or fungi, etc., apply 0.01 to 100 g of active ingredient compound per ¹ m2 to the soil or wood surface.

The compound of the present invention represented by the formula (1) can be used to protect grains, fruits, nuts, spices, tobacco, and other products from damage by lepidoptera, coleoptera, mites, fungi, and the like when the products are stored as is, in a powdered state, or mixed in the products. It can also protect animal products (skin, hair, wool, feathers, etc.) and plant products (cotton, paper, etc.) from attack by lepidoptera, coleoptera, blights, and cockroaches when stored in a natural or converted state, and can also protect foods such as meat and fish from attack by lepidoptera, coleoptera, flies, and mites when stored. In such situations, it can be controlled by spraying oils, emulsions, wettable powders, powders, etc., setting resin vaporizers, etc., treating with fumigants and aerosols, setting granules, tablets, and poison bait, spraying aerosols, and the like. These formulations can also be present as mixtures with other active compounds, such as insecticides, acaricides, nematicides, fungicides, repellents, and synergists, and these formulations can contain 0.0001 to 95% by weight of the active ingredient compounds in total.

The compound of the present invention represented by the formula (1) is valuable for the extermination or prevention of arthropods and fungi that parasitize the body surface of humans and livestock and cause direct harm by feeding on the skin or sucking blood, arthropods that spread diseases of humans and livestock or are vectors of such diseases, nematodes, trematodes, cestodes, protozoa, and arthropods that cause discomfort to humans. In such situations, the compound of the present invention can be mixed in small amounts into food or feed, or administered orally as an appropriate orally ingestible compounded pharmaceutical composition, such as tablets, pills, capsules, pastes, gels, beverages, medicated feed, medicated drinking water, medicated follow-up feed, sustained-release large pills, or other sustained-release devices that are retained in the gastrointestinal tract, containing pharma-ceutically acceptable carriers and coating substances, or administered transdermally as a spray, powder, grease, cream, ointment, emulsion, lotion, spot-on, pour-on, shampoo, etc. To achieve the desired effect in such applications, the formulation generally contains 0.0001 to 0.1% by mass, preferably 0.001 to 0.01% by mass, of the active ingredient compound. As a method of transdermal or local administration, a device (e.g., a collar, medallion, ear tag, etc.) attached to the animal to control arthropods locally or systemically can also be used.

Specific oral and transdermal administration methods for the compound of the present invention represented by the formula (1) when used as an anthelmintic for animals such as livestock and pets or humans are shown below, but the methods are not necessarily limited thereto.
When administered orally as medicated drinking water, the beverage is usually a solution, suspension or dispersion in a suitable non-toxic solvent or water together with a suspending agent such as bentonite or a wetting agent or other excipients. The beverage generally also contains an antifoaming agent. The beverage formulation generally contains 0.01 to 1.0% by weight, preferably 0.01 to 0.1% by weight, of the active compound.
When oral administration in a dry solid unit dosage form is desired, capsules, pills, tablets, etc., containing a predetermined amount of the active ingredient are usually used. These dosage forms are prepared by intimately mixing the active ingredient with a suitable finely divided diluent, filler, disintegrant, binder, such as starch, lactose, talc, magnesium stearate, vegetable gum, etc. Such unit dosage formulations can vary widely in mass and content of anthelmintic agent depending on the type of host animal to be treated, the degree of infection and type of parasite, and the weight of the host.

When administered via animal feed, it can be homogenously dispersed in the feed, used as a top dressing or in the form of pellets. In order to achieve the desired antiparasitic effect, the final feed contains 0.0001 to 0.05% by weight, preferably 0.0005 to 0.01% by weight, of the active ingredient compound.
The active compound dissolved or dispersed in a liquid carrier excipient can be parenterally administered 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 or cottonseed oil. Such formulations generally contain 0.05 to 50% by weight, preferably 0.1 to 5.0% by weight, of the active compound.
They may also be administered topically by mixing with a suitable carrier such as dimethylsulfoxide or a hydrocarbon solvent, and the formulation is applied directly to the external surface of the animal by spraying or direct pouring.
In addition, the compound of the present invention represented by the formula (1) can be used as an anthelmintic agent for arthropods that directly harm or arthropods that are vectors of diseases, etc., in the surrounding environment where such pests may be present, by spraying oils, emulsions, wettable powders, etc., injecting, irrigating, applying, spraying powders, etc., treating with heated aerosols such as fumigants, mosquito coils, self-burning fumigants, chemical reaction aerosols, fumigants such as fogging, ULV agents, etc., setting granules, tablets and poison bait, or adding floating powders, granules, etc. to waterways, wells, reservoirs, water tanks and other running or standing water. Furthermore, for agricultural or forest pests such as tussock moths, it is possible to control them in the same manner as described above, or for flies, etc., a method of mixing them into livestock feed so that they mix with feces, and for mosquitoes, a method of volatilizing them into the air using an electric mosquito repellent, etc. are also effective. In addition, the formulations having these usage forms can also be present as mixtures with other active compounds, such as pest control agents, acaricides, nematode control agents, disease control agents, repellents, and synergists, and these formulations contain the active ingredient compounds in a total amount of 0.0001 to 95 mass%.

The compound of the present invention represented by the formula (1) can also be used as a mixture with other active compounds. In particular, by mixing with a compound (insecticide) having insecticidal activity, acaricidal activity, or nematode repellent activity, it is possible to expand the range of pests to be controlled for the control of pests such as arthropods, gastropods, and nematodes that cause damage to plants, and synergistic effects such as reduced dosage can also be expected. Specific examples of such active compounds include the following.

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

Pyrethroids, such as acrinathrin, allethrin, bifenthrin, cycloprothrin, cyfluthrin, cyhalothrin, cyphenothrin, cypermethrin, deltamethrin, etofenprox, fenpropathrin, fenvalerate, flucythrinate , flufenprox, fluvalinate, furamethrin, halofenprox, imiprothrin, permethrin, phenothrin, prallethrin, pyrethrins, resmethrin, silafluofen, tefluthrin, tralomethrin, transfluthrin, etc.;
Neonicotinoid agents, such as acetamiprid, clothianidin, dinotefran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, and the like;
Diamide agents, such as chlorantraniliprole, cyantraniliprole, cyclaniliprole, flubenziamide, tetraniliprole, and the like;
Phenylpyrazole agents, such as ethiprole, fipronil, acetoprole, pyrafluoprole, pyriprole, etc.;
Nereistoxins, such as bensultap, cartap, thiocyclam, thiosultap, etc.;
Insect growth regulators such as phenylbenzoyl ureas and diacylhydrazines, for example, chlorfluazuron, diflubenzuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron, buprofezin, chromafenozide, halofenozide, methoxyfenozide, tebufenozide, cyromazine, etc.;
Juvenile hormone agents, such as diofenolan, fenoxycarb, hydroprene, methoprene, pyriproxyfen, and the like;

Insecticidal substances produced by microorganisms, such as abamectin, emamectin-benzoate, ivermectin, lepimectin, milbemectin, nemadectin, nikkomycin, polyoxin complex, spinetram, spinosad, BT agents, etc.;
Insecticidal substances derived from natural products, for example, anabasine, azadirachtin, deguelin, fatty acid glyceride, hydroxypropyl starch, soybean lecithin, nicotine, nornicotine, sodium oleate, petroleum oil, propylene glycol monolaurate, rapeseed oil, rotenone, sorbitan fatty acid ester, starch, etc.;
Other insecticides include afidpyropen, benzpyrimoxan, broflanilide, chlorfenapyr, diafenthiuron, dichloromezotiaz, dimpropyridaz, and DBEDC (Dodecylbenzenesulphonic acidbisethylenediamine copper [II]). salt), flonicamid, flometoquin, flufenerim, flupyradifurone, flupyrimin, fluralaner, fluhexafon, fluxametamide, hydramethylnon, indoxacarb, isocycloseram, metaflumizone, metaldehyde, nicotine sulfate sulfate), oxazosulfyl, pymetrozine, pyridalyl, pyrifluquinazon, spirotetramat, sulfoxaflor, tolfenpyrad, triazamate, triflumezopyrim, tyclopyrazoflor, and the like;

Acaricides such as acequinocyl, acinonapyr, amidoflumet, amitraz, azocyclotin, benzoximate, bifenazate, binapacryl, phenisobromorate, chinomethionat, clofentezine, cyenopyrafen, cyflumetofen, tricyclohexyltin hydroxide, dicofol, dienochlor, etoxazole, fenazaflor, fenazaquin, fenbutatin oxide oxide), fenothiocarb, fenpyroximate, fluacrypyrim, hexythiazox, pyrimidifen, polynactins, propargite, pyflubumide, pyridaben, spirodiclofen, spiropidion, spiromesifen, tebufenpyrad, tetradifon and flupentiofenox, etc.:
Nematicides, such as aluminum phosphide, benclothiaz, cadusafos, ethoprophos, fluazaindolizine, fluensulfone, fosthiazate, furfural, imicyafos, levamisol hydrochloride, mesulfenfos, metam-ammonium, methyl isocyanate, morantel tartarate, oxamyl, thioxazafen, etc.;
Examples of poison bait include chlorphacinone, coumatetralyl, diphacinone, sodium fluoracetate, warfarin, and the like.

The compound of the present invention represented by the formula (1) can also be used as a mixture with other active compounds other than compounds having pest control activity, acaricidal activity, or nematode control activity. In order to control diseases and/or weeds that occur simultaneously during the period of use, by mixing with a compound having fungicidal activity, herbicidal activity, or plant growth regulating activity, synergistic effects such as reduced dosage and reduced control labor can be expected. In addition, by mixing with a repellent or synergist, more effective control effects such as synergistic effects can be expected.

Specific examples of the active compound include disease control agents, such as
DD (1,3-dichloropropene), acibenzolar-S-methyl, aldimorph, ametoctradin, amisulbrom, andoprim, anilazine, azaconazole, azoxystrobin, basic copper sulfate, benodanil, benomyl, benthiavalicarb-isopropyl, benthiazole, bitertanol, bixafen, blasticidin S, boscalid, bromuconazole, calcium carbonate, buthiobate, lime sulfur mixture polysulfide), captafol, captan, carbendazim, carboxin, carpropamid, chinomethionat, chlorfenazole, chloroneb, chloropicrin, chlorothalonil, chlozolinate, DBEDC (complex of bis(ethylenediamine)copper-bis(dodecylbenzenesulfonic acid)), copper hydroxide, copper nonylphenol sulfonate, basic copper chloride oxychloride), cyazofamid, cyflufenamid, cymoxanil, cyproconazole, cyprodinil, dazomet, diclobutrazol, dichlofluanid, dichloclone, diclocymet, diclomezine, diethofencarb, difenoconazole, diflumetrim torim), dimethomorph, dimoxystrobin, diniconazole, diniconazole-M, dithane-stainless, dithianon, dodine, echlomezole, edifenphos, enestrobin, epoxiconazole, etaconazole, etaboxam, extract from shiitake mushroom mycelium mushroom), famoxadone, fenamidone, fenarimol, fenbuconazole, fenfuram, fenhexamid, fenoxanil, fenpiclonil, fenpropidin, fenpyrazamine, ferimzone, fluazinam, flumetover, flumorph, fluopicolide, fluopyram, fluoroimide, fluotrimazole, fluoxastrobin, fluquinconazo fluquinconazole, flusulfamide, flutolanil, fluxapyroxad, folpet, fosetyl-AL, fthalide, fuberidazole, fludioxonil, flusilazole, flutianil, flutriafol, furametpyr, fluconazole, guazatine, hexaconazole, hydroxyisoxazole, hymexazol, imazalil, imazalil sulfate sulfate), imibenconazole, iminoctadine acetate, iminoctadine-DBS,

Ipconazole, IBP (iprobenfos), iprodione, iprovalicarb, isofetamide, isoprothiolane, isopyrazam, isotianil, kasugamycin, kresoxim-methyl, mancozeb, mandipropamid, maneb, manzeb, mepanipyrim, mepronil, metalaxyl, metam-ammonium, metam-sodium, metconazole, methasulfocarb, methyl bromide bromide, methylisothiocyanate, metominostrobin, metrafenone, mildiomycin, myclobutanil, nickel dimethyldithiocarbamate, nuarimol, orysastrobin, oxadixyl, oxathiapiprolin, oxine-copper, oxolinic acid, oxpoconazole fumarate fumarate, oxycarboxin, oxytetracycline, pebulate, pefurazoate, penconazole, pencycuron, penflufen, penthiopyrad, picarbutrazox, picoxystrobin, piperalin, polycarbamate, polyoxin-B, polyoxins, potassium hydrogen carbonate, probenazole, prochloraz, procymidone, propamocarb, propiconazole, propineb, proquinazid,

Prothioconazole, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyrazophos, pyribencarb, pyridinitril, pyrifenox, pyrimethanil, pyriophenone, pyroquilon, quinoxyfen, quintozene, sedaxane, silver, simeconazole, sodium hydrogen carbonate, sodium hypochlorite hypochlorite, spiroxamine, streptomycin, sulfur, tebufloquin, tebuconazole, tecloftalam, terbinafine, tetraconazole, thiabendazole, thiadiazin, thifluzamide, thiophanate, thiophanate-methyl, thiram, tiadinil, tolclofos-methyl Examples include aryl, tolprocarb, tolylfluanid, triadimefon, triadimenol, triclopyricarb, tricyclazole, tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole, uniconazole-P, validamycin (-A), vinclozolin, zarilamid, zinc sulfate, zineb, ziram, and zoxamide.

Examples of compounds having herbicidal activity include
Aclonifen, acifluofen n-sodium, alachlor, alloxydim, amicarbazone, amidosulfuron, anilofos, asulam, atrazine, azimsulfuron, benfuresate, bensulfuron-methyl, bentazone, benthiocarb, benzobicyclon, benzofenap, bialaphos, bifenox, bromobutide, bromoxynil, butamifos, cafenstrole, calcium peroxide peroxide), carbetamide, cinosulfuron, clomeprop, cyclosulfamuron, cyhalofop-butyl, daimuron, desmedipham, diclofop-methyl, diflufenican, dimefuron, dimethametryn, dinoterube dinoterb), diquat, diuron, esprocarb, ethiozin, ethofumesate, ethoxysulfuron, etobenzanid, fenoxaprop-P-ethyl, fentrazamide, flucarbazone, flufenacet, flurtamone,

fluthiacet-methyl, foramsulfuron, glufosinate-ammonium, glyphosate-isopropylamine, glyphosate-trimesium, imazapyr, imazosulfuron, indanofan, iodosulfuron, ioxynil-octanoate, isoproturon, isoxadifen, isoxaflutole, lactofen, linuron , mefenacet, mesosulfuron, metamitron, methabenzthiazuron, metosulam, metribuzin, naproxamide, neburon, oxadiargyl, oxadiazon, oxaziclomefone, paraquat, pendimethalin, pentoxazone, phenmedipham, pretilachlor, propoxycarbazone, prosulfocarb, pyraclonil, pyraflufe n-ethyl, pyrazolate, pyrazosulfuron ethyl Examples include n-ethyl), pyributicarb, pyriftalid, pyriminobac-methyl, quizalofop-ethyl, sethoxydim, simazine, sulcotrione, sulfentrazone, thenylchlor, triaziflam, and tribufos.

In addition, examples of compounds having a plant growth regulating effect include:
1-naphthylacetamide, 4-CPA, benzylaminopurine, butralin, calcium chloride, calcium formate, calcium peroxide, calcium sulfate, chlormequat chloride, choline, cyanamide, cyclanilide, daminozide, decyl alcohol, dichlorprop, ethephon, ethychlozate, flurprimidol, forchlorfenuron, gibberellic acid, indolebutyric acid, maleic hydrazide potassium It can also be used in a mixture with benzoyl peroxidase, ...
Repellents such as capsaicin, carane-3,4-diol, citronellal, deet, dimethyl phthalate, hinokitiol, limonene, linalool, menthol, menthone, naphthalene, thiram, etc.;
Examples of synergists include methylenedioxynaphthalene, naphthyl propynyl ether, nitrobenzyl thiocyanate, octachlorodipropyl ether, pentyny! phthalimide, phenyl salioxon, piperonyl butoxide, safrole, sesamex, sesamin, sulfoxide, triphenyl phosphate, and verbutin.

The compounds of the present invention can be used as biological pesticides, for example, in the preparation of viruses such as Cytoplasmic polyhedrosis virus (CPV), Entomopox virus (EPV), Granulosis virus (GV), and Nuclear polyhedrosis virus (NPV), as well as in the preparation of insecticides such as Beauveria bassiana, Beauveria brongniartii, Monacrosporium phymatophagum, Paecilomyces fumosoroseus, Pasteuria penetrans, Steinernema carpocapsae, Steinernema glaseri, and Steinernema kushidae. Microbial pesticides used as insecticides or nematocides, such as Agrobacterium radiobactor, Bacillus subtilis, non-pathogenic Erwinia carotovora, non-pathogenic Fusarium oxysporum, Pseudomonas CAB-02, Pseudomonas fluorescens, Talaromyces flavus, Trichoderma atroviride, Trichoderma lignorum, etc.; Microbial pesticides used as fungicides, such as Xanthomonas campestris, A similar effect can be expected by mixing it with biological pesticides used as herbicides such as P. campestris.

In addition, as biological pesticides, for example, Amblyseius californicus, Amblyseius cucumeris, Amblyseius degenerans, Aphidius colemani, Aphidoletes aphidimyza, Chrysoperia carnea, Dacnusa sibirica, Diglyphus isaea, Encarsia formosa, Eretmocerus eremicus, Franklinothrips vespiformis, Harmonia axyridis, Hemiptarsenus It can also be used in combination with natural enemies such as Neochrysocharis formosa, Orius sauteri, Orius strigicollis, Phytoseiulus persimilis, Pilophorus typicus, and Piocoris varius, as well as pheromones such as codlelure, cuelure, geraniol, gyptol, liblure, looplure, methyl eugenol, orfralure, peachflure, phycilure, pyrimalure, and turpentine.

The present invention will be explained in more detail below with reference to examples, formulation examples, and test examples, but the scope of the present invention is not limited in any way by these examples, formulation examples, and test examples.

Example 1
Synthesis of N'-(1-(4-fluorophenyl)-2-methyl-2-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)propylidene)formhydrazide (compound number: A-11):

1-1: Synthesis of 1-(4-fluorophenyl)-2-methyl-2-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)propan-1-one (compound number: C-5) Potassium carbonate (3.1 g) was added to a solution of 3-trifluoromethyl-1,2,4-triazole (2.8 g) and 2-bromo-1-(4-fluorophenyl)-2-methylpropan-1-one (5.0 g) in N,N-dimethylformamide (35 ml). The reaction solution was stirred at room temperature for 3 hours, and then water (60 ml) and ethyl acetate (80 ml) were added. The organic layer was separated, and then further washed with water. After the organic layer was dried over _MgSO4 , the organic solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 2.4 g of 1-(4-fluorophenyl)-2-methyl-2-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)propan-1-one (mp 80-84 °C).

実施例２
N'-(1-(4-フルオロフェニル)- 2-メチル-2-(3－(トリフルオロメチル)－１H-1,2,4－トリアゾール-１-イル)プロピリデン)- N-(2-プロピニル)ホルムヒドラジド (化合物番号：A-68) の合成：
N'-(1-(4-フルオロフェニル)-2-メチル-2-(3－(トリフルオロメチル)－１H-1,2,4－トリアゾール-１-イル)プロピリデン)ホルムヒドラジド（化合物番号：A-11）(0.21g)をN,N-ジメチルホルムアミド(3ml)に溶解させ、炭酸カリウム(0.11g)を加え、攪拌し、室温でプロパルギルブロマイド(0.05ml)を添加し、室温で3時間攪拌した。反応液に酢酸エチルと水を加え、有機層を分離後、更に有機層を水洗した。有機層をMgSO₄で乾燥後、有機溶媒を減圧留去し、残渣をシリカゲルカラムクロマトグラフィーで精製して、N'-(1-(4-フルオロフェニル)- 2-メチル-2-(3－(トリフルオロメチル)－１H-1,2,4－トリアゾール-１-イル)プロピリデン)- N-(2-プロピニル)ホルムヒドラジド（化合物A-68）を0.19ｇ（油状物）で得た。

1-2: Synthesis of N'-(1-(4-fluorophenyl)-2-methyl-2-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)propylidene)formylhydrazide (Compound No.: A-11)
Hydrazine monohydrate (1.5 ml) and concentrated hydrochloric acid (2 drops) were added to a solution of 1-(4-fluorophenyl)-2-methyl-2-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)propan-1-one (compound number: C-5) (1.28 g) in ethanol (12 ml), and the mixture was stirred under reflux for 3 hours. After ethanol was distilled off from the reaction solution, water (80 ml) and ethyl acetate (60 ml) were added, and the organic layer was separated and further washed with water. After the organic layer was dried over MgSO ₄ , the organic solvent was distilled off under reduced pressure to obtain 1-(1-(4-fluorophenyl)-1-hydrazinylidene-2-methylpropan-2-yl)-3-(trifluoromethyl)-1H-1,2,4-triazole as a residue. The unpurified product was dissolved in ethyl formate (15 ml), formic acid (0.4 ml) was added, and the reaction solution was refluxed for 3 hours, then returned to room temperature and allowed to stand overnight. The organic solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 0.65 g of N'-(1-(4-fluorophenyl)-2-methyl-2-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)propylidene)formhydrazide (compound number: A-11) (mp 144-147 °C).

Example 2
Synthesis of N'-(1-(4-fluorophenyl)-2-methyl-2-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)propylidene)-N-(2-propynyl)formhydrazide (compound number: A-68):
N'-(1-(4-fluorophenyl)-2-methyl-2-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)propylidene)formhydrazide (compound number: A-11) (0.21 g) was dissolved in N,N-dimethylformamide (3 ml), potassium carbonate (0.11 g) was added, the mixture was stirred, propargyl bromide (0.05 ml) was added at room temperature, and the mixture was stirred at room temperature for 3 hours. Ethyl acetate and water were added to the reaction solution, and the organic layer was separated, and then the organic layer was washed with water. After the organic layer was dried over _MgSO4 , the organic solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 0.19 g (oil) of N'-(1-(4-fluorophenyl)-2-methyl-2-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)propylidene)-N-(2-propynyl)formhydrazide (compound A-68).

３－２：1-(1-(4-クロロフェニル)-1-ヒドラジニリデン-2-メチルプロパン-2-イル)-3-(トリフルオロメチル)-1H-1,2,4- トリアゾールの合成(化合物番号：B-4)

1-(4-クロロフェニル)- 2-メチル-2-(3-(トリフルオロメチル)-1H-1,2,4-トリアゾール-1-イル)プロパン-1-オン(C-7)(4.0g)をエタノール(30ml)に溶解し、ヒドラジン水和物(4.0g)及び濃塩酸(0.2ml)を加えた。反応液を3時間80℃で撹拌した。反応液を室温に戻し、減圧濃縮によりエタノールを留去した後に水(70ml )と酢酸エチル( 40ml )を加え、有機層を分離後、更に、有機層を水洗した。有機層をMgSO₄で乾燥後、有機溶媒を減圧留去し1-(1-(4-クロロフェニル)-1-ヒドラジニリデン-2-メチルプロパン-2-イル)-3-(トリフルオロメチル)-1H-1,2,4- トリアゾールを3.32g(固体)を得た。得られた化合物は更なる生成をせずに次の反応に用いた。

３－３：N’-(1-(4-クロロフェニル)-2-メチル-2-(3-トリフルオロメチル)-1H-1,2,4-トリアゾール-1-イル)プロピリデン）-N,N-ジメチルホルムヒドラゾンアミド(化合物番号：A-7) の合成：

1-(1-(4-クロロフェニル)-1-ヒドラジニリデン-2-メチルプロパン-2-イル)-3-(トリフルオロメチル)-1H-1,2,4- トリアゾール（化合物番号：B-4）（0.40g)をトルエン(5ml）に溶解し、N,N-ジメチルホルムアミドジメチルアセタール(0.5ml)を加え、反応液を２時間還流した。有機溶媒を減圧留去し、残渣をシリカゲルカラムクロマトグラフィーで精製して、N’-(1-(4-クロロフェニル)-2-メチル-2-(3-トリフルオロメチル)-1H-1,2,4-トリアゾール-1-イル)プロピリデン）-N,N-ジメチルホルムヒドラゾンアミド（化合物A-8）
を0.29ｇ（固体）で得た。

Example 3
Synthesis of N'-(1-(4-chlorophenyl)-2-methyl-2-(3-trifluoromethyl)-1H-1,2,4-triazol-1-yl)propylidene)-N,N-dimethylformhydrazonamide (A-8):

3-1: Synthesis of 1-(4-chlorophenyl)-2-methyl-2-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)propan-1-one (compound number: C-7)
2-Bromo-1-(4-chlorophenyl)-2-methylpropan-1-one (5.2 g) was dissolved in N,N-dimethylformamide (25 ml), and 3-trifluoromethyl-1,2,4-triazole (3.02 g) and potassium carbonate (3.04 g) were added. After stirring the reaction solution at room temperature for 5 hours, water (150 ml) and ethyl acetate (80 ml) were added, and the organic layer was separated and further washed with water. After drying the organic layer with MgSO ₄ , the organic solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 1-(4-chlorophenyl)-2-methyl-2-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)propan-1-one (11.05 g, mp 69-73°C).

3-2: Synthesis of 1-(1-(4-chlorophenyl)-1-hydrazinylidene-2-methylpropan-2-yl)-3-(trifluoromethyl)-1H-1,2,4-triazole (Compound No.: B-4)

1-(4-chlorophenyl)-2-methyl-2-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)propan-1-one (C-7) (4.0 g) was dissolved in ethanol (30 ml), and hydrazine hydrate (4.0 g) and concentrated hydrochloric acid (0.2 ml) were added. The reaction solution was stirred at 80°C for 3 hours. The reaction solution was returned to room temperature, and ethanol was removed by vacuum concentration. Water (70 ml) and ethyl acetate (40 ml) were added, and the organic layer was separated and further washed with water. The organic layer was dried over _MgSO4 , and the organic solvent was removed by vacuum distillation to obtain 1-(1-(4-chlorophenyl)-1-hydrazinylidene-2-methylpropan-2-yl)-3-(trifluoromethyl)-1H-1,2,4-triazole (3.32 g, solid). The compound obtained was used in the next reaction without further purification.

3-3: Synthesis of N'-(1-(4-chlorophenyl)-2-methyl-2-(3-trifluoromethyl)-1H-1,2,4-triazol-1-yl)propylidene)-N,N-dimethylformhydrazonamide (compound number: A-7):

1-(1-(4-chlorophenyl)-1-hydrazinylidene-2-methylpropan-2-yl)-3-(trifluoromethyl)-1H-1,2,4-triazole (compound number: B-4) (0.40 g) was dissolved in toluene (5 ml), N,N-dimethylformamide dimethyl acetal (0.5 ml) was added, and the reaction solution was refluxed for 2 hours. The organic solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography to obtain N'-(1-(4-chlorophenyl)-2-methyl-2-(3-trifluoromethyl)-1H-1,2,4-triazol-1-yl)propylidene)-N,N-dimethylformhydrazonamide (compound number: A-8).
was obtained in 0.29 g (solid).

Example 4
Synthesis of ethyl N-(1-(3-fluorophenyl)-2-methyl-2-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)propylidene)formylhydrazonate (compound number: A-79)

1-(3-fluorophenyl)-2-methyl-2-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)propan-1-one (compound number: C-12) (2.0 g) obtained in the same manner as in 1-1 was dissolved in ethanol (15 ml), and hydrazine hydrate (2 ml) and concentrated hydrochloric acid (0.1 ml) were added. The reaction solution was stirred under reflux for 3 hours. The reaction solution was returned to room temperature, and the ethanol was removed by vacuum concentration. Water (40 ml) and ethyl acetate (20 ml) were added, and the organic layer was separated. The organic layer was further washed with water. The organic layer was dried over MgSO ₄ , and the organic solvent was removed under reduced pressure to obtain crude 1-(1-(3-fluorophenyl)-1-hydrazinylidene-2-methylpropan-2-yl)-3-(trifluoromethyl)-1H-1,2,4-triazole (B-17) (oil).
0.40 g of the obtained crude 1-(1-(3-fluorophenyl)-1-hydrazinylidene-2-methylpropan-2-yl)-3-(trifluoromethyl)-1H-1,2,4-triazole (B-17) was dissolved in toluene (5 ml), ethyl orthoformate (0.8 ml) was added, and the reaction solution was stirred at 105° C. for 1.5 hours. The organic solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain ethyl N-(1-(3-fluorophenyl)-2-methyl-2-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)propylidene)formylhydrazonate (compound A-79) in the form of 0.25 g (oil).

The ¹ H-NMR data for the following compounds prepared in the same manner as in the above Examples are shown in Tables 4 to 6. In Tables 4 to 6, the compound numbers correspond to those in Tables 1 to 3, respectively.

Various formulation examples containing the compound of the present invention are specifically described below, but the compound of the present invention, auxiliary ingredients, and the amounts of these ingredients added are not limited to the following formulation examples. Note that all parts in the formulation examples refer to parts by mass.

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

Formulation Example 2: Wettable powder The compound of the present invention (20 parts), Toxil GU-N (white carbon, Oriental Silicas Corporation) (20 parts), Sorpol 5096 (polyoxyethylene styryl phenyl ether sulfate, Toho Chemical Industry Co., Ltd.) (10 parts), and SS Clay (clay, Showa KDE Corporation) (50 parts) were mixed and pulverized using a pulverizer to obtain a wettable powder.

Formulation Example 3 Water-soluble Compound The compound of the present invention (5 parts), Lunox P-65L (sodium alkylbenzenesulfonate, Toho Chemical Industry Co., Ltd.) (3 parts), and sodium hydrogen carbonate (reagent) (92 parts) were uniformly mixed and then pulverized using a pulverizer to obtain a water-soluble compound.

Formulation Example 4 Flowable The compound of the present invention (20 parts), Sorpol 7948 (polyoxyalkylene tristyryl phenyl ether sodium sulfate, Toho Chemical Industry Co., Ltd.) (5 parts), propylene glycol (reagent) (10 parts), and water (40 parts) were mixed in advance and wet-pulverized in a bead mill to obtain a slurry. Next, KELZAN (xanthan gum, Sansho Co., Ltd.) (0.2 parts) was thoroughly mixed and dispersed in water (24.8 parts) to prepare a gel-like material, which was thoroughly mixed with the pulverized slurry to obtain a flowable.

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

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

Formulation Example 7 Microemulsion A microemulsion was obtained by uniformly mixing the compound of the present invention (10 parts), xylene (reagent) (20 parts), Newcalgen D-230 (polyoxyethylene castor oil, Takemoto Oil & Fat Co., Ltd.) (20 parts), Airroll CT-1L (dioctyl sodium sulfosuccinate, Toho Chemical Industry Co., Ltd.) (2.0 parts), and water (48 parts).

Formulation Example 8 Liquid Preparation The compound of the present invention (20 parts), N-methyl-2-pyrrolidone (reagent) (70 parts), and Newcalgen D-230 (polyoxyethylene castor oil, Takemoto Oil Co., Ltd.) (10 parts) were uniformly mixed and dissolved to obtain a liquid preparation.

Formulation Example 9 Granules-1
The compound of the present invention (5 parts), Airroll CT-1L (dioctyl sodium sulfosuccinate, Toho Chemical Industry Co., Ltd.) (2 parts), Bentonite Sado (bentonite, Kunimine Kogyo Co., Ltd.) (30 parts), and NK-300 (clay, Showa KDE Co., Ltd.) (63 parts) were uniformly mixed, water was added, and the mixture was thoroughly kneaded, followed by extrusion granulation and drying/sizing to obtain granules.

Formulation Example 10 Granules-2
The compound of the present invention (5 parts) was dissolved in methanol (reagent), and the solution was adsorbed onto Ishikawa Light No. 2 (95 parts) using a tumbling granulator, followed by drying to obtain granules.

Formulation Example 11 Microgranules-1
The compound of the present invention (2 parts) was dissolved in methanol (reagent), and the solution was adsorbed onto Ishikawa Light No. 4 (98 parts) using a tumbling granulator, followed by drying to obtain fine granules.

Formulation Example 12 Microgranules-2
The compound of the present invention (5 parts) and Toxil GU-N (5 parts) were mixed and then pulverized using a fine grinding machine, and uniformly mixed with Iide quartz sand (silica sand, JFE Mineral Co., Ltd.) (80 parts). This mixture was further mixed while spraying an aqueous solution of Toxanon GR-31A (polycarboxylic acid type surfactant, Sanyo Chemical Industries, Ltd.) (10 parts) diluted with water to obtain a granular composition. This granular composition was dried to obtain a fine granule.

Formulation Example 13: Powder The compound of the present invention (5 parts), Toxil GU-N (5 parts) and Omori Fine Clay (clay, Omori Sangyo Co., Ltd.) (90 parts) were uniformly mixed and then pulverized using a pulverizer to obtain a powder.

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

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

Formulation Example 16 Seed Coating Flowable The compound of the present invention (10 parts), Sorpol 7948 (5 parts), propylene glycol (reagent) (10 parts) and water (40 parts) were mixed in advance and wet-milled with a bead mill. Next, KELZAN (xanthan gum, Sansho Co., Ltd.) (0.2 parts) and water (29.8 parts) were thoroughly mixed and dispersed, and AMECOAT HCA/83 (acrylic acid polymer, SOLVAY) (5 parts) was mixed to prepare a gel-like material. The milled slurry and the prepared gel-like material were thoroughly mixed to obtain a flowable. The flowable was mixed with seeds and air-dried to obtain coated seeds.

比較剤Ａ （特許文献１：特開平8-073436号公報記載のNo.6） The effects and usefulness of the compounds of the present invention will now be described in detail with reference to the following examples. The compounds used for comparison are indicated by the following compound symbols.

Comparative agent A (Patent Document 1: No. 6 in JP-A-8-073436)

Test Example 1: Efficacy test against sweet potato root-knot nematode (Meloidogyne incognita (Kofoid et White) Chitwood) 200 ml of test soil, adjusted to a nematode density of 200 nematodes/20 g of soil, was placed in a polystyrene cup (diameter 9 cm, height 6.5 cm), and 50 ml of a water-diluted solution (100 ppm) of an emulsion prepared according to Formulation Example 1 was irrigated, after which tomatoes were sown (13 seeds/pot). After sowing, the plants were grown in a greenhouse. On the 17th day after sowing, the degree of root galling of each plant was investigated on a 5-point scale based on the following evaluation criteria, and the root-knot index and further the control value were calculated based on the following formula.

Severity of root galls (rating criteria): 0 (no root galls), 1 (1-2 root galls), 2 (3 or more root galls), 3 (large root galls or connected root galls present; less than 50% of the roots), 4 (root galls present on 50% or more of the roots)

Root knot index = Σ (degree of root knot x number of plants) / (4 x number of plants surveyed)

Control value (%) = [1 - (root and nodule index of treated area/root and nodule index of untreated area)] x 100

As a result, compound numbers A-1, A-2, A-3, A-5, A-6, A-7, A-8, A-9, A-11, A-13, A-21, A-22, A-25, A-26, A-29, A-33, A-34, A-35, A-36, A-37, A-38, A-39, A-40, A-41, A-42, A-43, A-44, A-45, A-46, A The compounds of the present invention, A-47, A-50, A-54, A-62, A-63, A-67, A-68, A-69, A-70, A-71, A-72, A-73, A-74, A-75, A-76, A-77, A-78, A-79, A-80, A-81, A-82, A-83, A-84, A-85, B-1, and B-4, showed a control rate of 70% or more. On the other hand, the control rate of the comparative agent A was 0%.

Test Example 2: Density suppression test against tomato rust mite (Aculops lycopersici Massee) A polyethylene cup with a capacity of 430 ml containing water was covered with a lid with a hole (diameter about 5 mm) in the center. A circular filter paper with a diameter of 6.5 cm was cut with a width of about 5 mm, and the strip-like part hanging down was inserted through the hole in the lid so that it was immersed in the water in the cup, and absorbent cotton was placed on the filter paper. In this way, three leaf disks (1 cm x 1 cm) made from tomato leaflets at the initial stage of true leaf development were placed on the absorbent cotton in a state in which the water in the cup was constantly replenished, with the underside of the leaf facing up, and small pieces of leaves infested with tomato rust mite were inoculated on the disks. 24 hours after inoculation, the small pieces were removed, and the cup was placed in an acrylic cylinder with a height of 50 cm and a diameter of 10 cm, and a water-diluted solution (500 ppm) of the emulsion prepared according to Formulation Example 1 was sprayed using an airbrush in an amount of 2.0 ml per cup. After spraying, the mixture was kept in a thermostatic chamber at 25°C. Seven days after treatment, the mixture was evaluated on a four-point scale: 100 (next-generation density suppression rate: 100%), 80 (same: 99-80%), 50 (same: 79-50%), and 0 (same: less than 50%). Based on the results, the control rate was calculated using the following formula. The test was carried out using one cup from each section.

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

A: 100 disks, B: 80 disks, C: 50 disks, D: 0 disks

As a result, the compounds of the present invention, compound numbers A-1, A-2, A-3, A-9, A-21, A-25, A-26, A-33, A-34, A-36, A-45, A-46, A-47, A-50, A-62, A-68, A-69, A-70, A-71, A-72, A-73, A-74, A-75, A-77, A-79, A-80, A-81, A-82, and B-21, showed a control rate of 90% or more. On the other hand, the control rate of the comparative agent A was 0%.

As described above, the compound of the present invention is highly effective as an agricultural and horticultural pesticide, particularly as an agricultural and horticultural pest control agent or nematode control agent. It is also highly effective against pests that parasitize pets such as dogs and cats, and livestock such as cows and sheep.

Claims (15)

The following formula (1):

[In the formula, R ₁ represents a hydrogen atom, a C _1-6 alkyl group, a C _1-6 alkoxy C _1-6 alkyl group, a C _2-6 alkenyl group, a C _2-6 alkynyl group or an optionally substituted benzyl group,
_R2 represents a formyl group, or
R ₁ and R ₂ together represent the following formula:

may form a group represented by
_R5 represents _{OR6 or NR7R8} ;
_R6 represents a _C1-6 alkyl group or a _C1-6 haloalkyl group;
_R7 represents a hydrogen atom or a _C1-6 alkyl group;
_R8 represents a hydrogen atom, a _C1-6 alkyl group, a _C1-6 haloalkyl group, a _hydroxyC1-6 alkyl group, a _{C1-6 alkoxyC1-6} alkyl group, _{a C3-6} cycloalkylC1-6 alkyl group, a _C1-6 alkoxy group, a _C2-6 alkenyl group, a _C2-6 haloalkenyl group, a _C2-6 alkynyl group, a _C2-6 haloalkynyl group, a _C3-6 cycloalkyl group or an optionally substituted benzyl group, or
R ₇ and R ₈ together with the nitrogen atom to which they are attached may form a saturated or unsaturated 4- to 7-membered ring;
_R3 and _R4 each independently represent a _C1-6 alkyl group;
X, or when a plurality of Xs are present, each of the plurality of Xs independently represents a hydrogen atom, a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _3-6 cycloalkyl group, a C _3-6 halocycloalkyl group, a C _2-6 alkenyl group, a C _2-6 haloalkenyl group, a C _2-6 alkynyl group, a C _2-6 haloalkynyl group, a C _1-6 alkoxy group, a C _1-6 haloalkoxy group, a C _1-6 alkylthio group, a C _1-6 alkylsulfinyl group, a C _1-6 alkylsulfonyl group, a C _1-6 alkoxycarbonyl group, a formyl group, a halogen atom, a cyano group or a nitro group, or two Xs present on two adjacent carbon atoms may form a saturated or unsaturated 5- or 6-membered ring together with the carbon atoms to which each X is bonded,
n represents an integer from 1 to 5;
Y ₁ , Y ₂ , Y ₃ and Y ₄ each independently represent a nitrogen atom or a CR group;
R, or when there are multiple R, each of the multiple Rs independently represents a hydrogen atom, a _C1-6 haloalkyl group, a halogen atom, a cyano group, or a nitro group.
A hydrazone derivative represented by the formula: The hydrazone derivative or its salt according to claim 1, wherein _Y2 represents CR and R represents a _C1-6 haloalkyl group. The following formula (2):

[In the formula, R ₁ represents a hydrogen atom, a C _1-6 alkyl group, a C _1-6 alkoxy C _1-6 alkyl group, a C _2-6 alkenyl group, a C _2-6 alkynyl group or an optionally substituted benzyl group,
_R3 and _R4 each independently represent a _C1-6 alkyl group;
X, or when a plurality of Xs are present, each of the plurality of Xs independently represents a hydrogen atom, a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _3-6 cycloalkyl group, a C _3-6 halocycloalkyl group, a C _2-6 alkenyl group, a C _2-6 haloalkenyl group, a C _2-6 alkynyl group, a C _2-6 haloalkynyl group, a C _1-6 alkoxy group, a C _1-6 haloalkoxy group, a C _1-6 alkylthio group, a C _1-6 alkylsulfinyl group, a C _1-6 alkylsulfonyl group, a C _1-6 alkoxycarbonyl group, a formyl group, a halogen atom, a cyano group or a nitro group, or two Xs present on two adjacent carbon atoms may form a saturated or unsaturated 5- or 6-membered ring together with the carbon atoms to which each X is bonded,
n represents an integer from 1 to 5;
Y ₁ , Y ₂ , Y ₃ and Y ₄ each independently represent a nitrogen atom or a CR group;
R, or when there are multiple R, each of the multiple Rs independently represents a hydrogen atom, a _C1-6 haloalkyl group, a halogen atom, a cyano group, or a nitro group.
A hydrazone derivative represented by the formula: The following formula (3):

[In the formula, _R3 and _R4 each independently represent a _C1-6 alkyl group,
X, or when a plurality of Xs are present, each of the plurality of Xs independently represents a hydrogen atom, a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _3-6 cycloalkyl group, a C _3-6 halocycloalkyl group, a C _2-6 alkenyl group, a C _2-6 haloalkenyl group, a C _2-6 alkynyl group, a C _2-6 haloalkynyl group, a C _1-6 alkoxy group, a C _1-6 haloalkoxy group, a C _1-6 alkylthio group, a C _1-6 alkylsulfinyl group, a C _1-6 alkylsulfonyl group, a C _1-6 alkoxycarbonyl group, a formyl group, a halogen atom, a cyano group or a nitro group, or two Xs present on two adjacent carbon atoms may form a saturated or unsaturated 5- or 6-membered ring together with the carbon atoms to which each X is bonded,
n represents an integer from 1 to 5;
Y ₁ , Y ₂ , Y ₃ and Y ₄ each independently represent a nitrogen atom or a CR group;
R, or when there are multiple R, each of the multiple Rs independently represents a hydrogen atom, a _C1-6 haloalkyl group, a halogen atom, a cyano group, or a nitro group.
A ketone derivative represented by the formula: The following formula (4):

[In the formula, R ₁ represents a hydrogen atom, a C _1-6 alkyl group, a C _1-6 alkoxy C _1-6 alkyl group, a C _2-6 alkenyl group, a C _2-6 alkynyl group or an optionally substituted benzyl group,
_R3 and _R4 each independently represent a _C1-6 alkyl group;
X, or when a plurality of Xs are present, each of the plurality of Xs independently represents a hydrogen atom, a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _3-6 cycloalkyl group, a C _3-6 halocycloalkyl group, a C _2-6 alkenyl group, a C _2-6 haloalkenyl group, a C _2-6 alkynyl group, a C _2-6 haloalkynyl group, a C _1-6 alkoxy group, a C _1-6 haloalkoxy group, a C _1-6 alkylthio group, a C _1-6 alkylsulfinyl group, a C _1-6 alkylsulfonyl group, a C _1-6 alkoxycarbonyl group, a formyl group, a halogen atom, a cyano group or a nitro group, or two Xs present on two adjacent carbon atoms may form a saturated or unsaturated 5- or 6-membered ring together with the carbon atoms to which each X is bonded,
n represents an integer from 1 to 5;
Y ₁ , Y ₂ , Y ₃ and Y ₄ each independently represent a nitrogen atom or a CR group;
R, or when a plurality of Rs are present, each of the plurality of Rs independently represents a hydrogen atom, a C _1-6 haloalkyl group, a halogen atom, a cyano group, or a nitro group.
A method for producing a hydrazone derivative represented by the following formula:
The following formula (2):

[In the formula, R ₁ , R ₃ , R ₄ , X, Y ₁ , Y ₂ , Y ₃ , Y ₄ and n are as defined in the above formula (4).]
A hydrazone derivative represented by the following formula (5):

HCOOR ₉ (5)

[In the formula, _R9 represents a _C1-6 alkyl group.]
The method of producing the compound according to the present invention comprises reacting a compound represented by the formula: The following formula (6):

[In the formula, _R5 represents _{OR6 or NR7R8} ,
_R6 represents a _C1-6 alkyl group or a _C1-6 haloalkyl group;
_R7 represents a hydrogen atom or a _C1-6 alkyl group;
_R8 represents a hydrogen atom, a _C1-6 alkyl group, a _C1-6 haloalkyl group, a _hydroxyC1-6 alkyl group, a _{C1-6 alkoxyC1-6} alkyl group, _{a C3-6} cycloalkylC1-6 alkyl group, a _C1-6 alkoxy group, a _C2-6 alkenyl group, a _C2-6 haloalkenyl group, a _C2-6 alkynyl group, a _C2-6 haloalkynyl group, a _C3-6 cycloalkyl group or an optionally substituted benzyl group, or
R ₇ and R ₈ together with the nitrogen atom to which they are attached may form a saturated or unsaturated 4- to 7-membered ring;
_R3 and _R4 each independently represent a _C1-6 alkyl group;
X, or when a plurality of Xs are present, each of the plurality of Xs independently represents a hydrogen atom, a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _3-6 cycloalkyl group, a C _3-6 halocycloalkyl group, a C _2-6 alkenyl group, _{a C 2-6 haloalkenyl group, a C 2-6 alkynyl group, a C 1-6 alkylsulfinyl group, a C 1-6 alkylsulfonyl group , a} C _2-6 haloalkynyl group, a C _1-6 alkoxy group, a C _1-6 haloalkoxy group, a C 1-6 alkylthio group, a C _1-6 alkoxycarbonyl group, a formyl group, a halogen atom, a cyano group or a nitro group, or two Xs present on two adjacent carbon atoms may form a saturated or unsaturated 5- or 6-membered ring together with the carbon atoms to which each X is bonded,
n represents an integer from 1 to 5;
Y ₁ , Y ₂ , Y ₃ and Y ₄ each independently represent a nitrogen atom or a CR group;
R, or when there are multiple R, each of the multiple Rs independently represents a hydrogen atom, a _C1-6 haloalkyl group, a halogen atom, a cyano group, or a nitro group.
A method for producing a hydrazone derivative represented by the following formula:
The following formula (7):

[In the formula, _R3 , _R4 , X, _Y1 , _Y2 , _Y3 , _Y4 and n are as defined in the above formula (6).]
The hydrazone derivative represented by the following formula (8):

[In the formula, _R5 is as defined in the above formula (6), and _R9 each represents a _C1-6 alkyl group, and each may be the same or different.]
The method of producing the compound according to the present invention comprises reacting a compound represented by the formula: The following formula (9):

[In the formula, R ₇ represents a hydrogen atom or a C _1-6 alkyl group,
_R8 represents a hydrogen atom, a _C1-6 alkyl group, a _C1-6 haloalkyl group, a _hydroxyC1-6 alkyl group, a _{C1-6 alkoxyC1-6} alkyl group, _{a C3-6} cycloalkylC1-6 alkyl group, a _C1-6 alkoxy group, a _C2-6 alkenyl group, a _C2-6 haloalkenyl group, a _C2-6 alkynyl group, a _C2-6 haloalkynyl group, a _C3-6 cycloalkyl group or an optionally substituted benzyl group, or
R ₇ and R ₈ together with the nitrogen atom to which they are attached may form a saturated or unsaturated 4- to 7-membered ring;
_R3 and _R4 each independently represent a _C1-6 alkyl group;
X, or when a plurality of Xs are present, each of the plurality of Xs independently represents a hydrogen atom, a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _3-6 cycloalkyl group, a C _3-6 halocycloalkyl group, a C _2-6 alkenyl group, a C _2-6 haloalkenyl group, a C _2-6 alkynyl group, a C _2-6 haloalkynyl group, a C _1-6 alkoxy group, a C _1-6 haloalkoxy group, a C _1-6 alkylthio group, a C _1-6 alkylsulfinyl group, a C _1-6 alkylsulfonyl group, a C _1-6 alkoxycarbonyl group, a formyl group, a halogen atom, a cyano group or a nitro group, or two Xs present on two adjacent carbon atoms may form a saturated or unsaturated 5- or 6-membered ring together with the carbon atoms to which each X is bonded,
n represents an integer from 1 to 5;
Y ₁ , Y ₂ , Y ₃ and Y ₄ each independently represent a nitrogen atom or a CR group;
R, or when there are multiple R, each of the multiple Rs independently represents a hydrogen atom, a _C1-6 haloalkyl group, a halogen atom, a cyano group, or a nitro group.
A method for producing a hydrazone derivative represented by the following formula:
The following formula (10):

[In the formula, _R3 , _R4 , X, _Y1 , _Y2 , _Y3 , _Y4 and n are as defined in the above formula (8), and _R6 represents a _C1-6 alkyl group.]
The hydrazone derivative represented by the following formula (10):

[In the formula, _R7 and _R8 are as defined in the above formula (9)]
The method of producing the compound according to the present invention comprises reacting the compound with an amine derivative represented by the formula: The following formula (4):

[In the formula, R ₁ represents a C _1-6 alkyl group, a C _1-6 alkoxy C _1-6 alkyl group, a C _2-6 alkenyl group, a C _2-6 alkynyl group or an optionally substituted benzyl group,
_R3 and _R4 each independently represent a _C1-6 alkyl group;
X, or when a plurality of Xs are present, each of the plurality of Xs independently represents a hydrogen atom, a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _3-6 cycloalkyl group, a C _3-6 halocycloalkyl group, a C _2-6 alkenyl group, a C _2-6 haloalkenyl group, a C _2-6 alkynyl group, a C _2-6 haloalkynyl group, a C _1-6 alkoxy group, a C _1-6 haloalkoxy group, a C _1-6 alkylthio group, a C _1-6 alkylsulfinyl group, a C _1-6 alkylsulfonyl group, a C _1-6 alkoxycarbonyl group, a formyl group, a halogen atom, a cyano group or a nitro group, or two Xs present on two adjacent carbon atoms may form a saturated or unsaturated 5- or 6-membered ring together with the carbon atoms to which each X is bonded,
n represents an integer from 1 to 5;
Y ₁ , Y ₂ , Y ₃ and Y ₄ each independently represent a nitrogen atom or a CR group;
R, or when there are multiple R, each of the multiple Rs independently represents a hydrogen atom, a C _1-6 haloalkyl group, a halogen atom, a cyano group, or a nitro group.
A method for producing a hydrazone derivative represented by the following formula:
The following formula (12):

[In the formula, _R3 , _R4 , X, _Y1 , _Y2 , _Y3 , _Y4 and n are as defined in the above formula (4).]
The hydrazone derivative represented by the following formula (13):

[In the formula, _R1 is as defined in the above formula (4), and L represents a leaving group.]
The method of claim 1, further comprising reacting the compound represented by the formula: The following formula (2):

[In the formula, R ₁ represents a hydrogen atom, a C _1-6 alkyl group, a C _1-6 alkoxy C _1-6 alkyl group, a C _2-6 alkenyl group, a C _2-6 alkynyl group or an optionally substituted benzyl group,
_R3 and _R4 each independently represent a _C1-6 alkyl group;
X, or when a plurality of Xs are present, each of the plurality of Xs independently represents a hydrogen atom, a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _3-6 cycloalkyl group, a C _3-6 halocycloalkyl group, a C _2-6 alkenyl group, a C _2-6 haloalkenyl group, a C _2-6 alkynyl group, a C _2-6 haloalkynyl group, a C _1-6 alkoxy group, a C _1-6 haloalkoxy group, a C _1-6 alkylthio group, a C _1-6 alkylsulfinyl group, a C _1-6 alkylsulfonyl group, a C _1-6 alkoxycarbonyl group, a formyl group, a halogen atom, a cyano group or a nitro group, or two Xs present on two adjacent carbon atoms may form a saturated or unsaturated 5- or 6-membered ring together with the carbon atoms to which each X is bonded,
n represents an integer from 1 to 5;
Y ₁ , Y ₂ , Y ₃ and Y ₄ each independently represent a nitrogen atom or a CR group;
R, or when there are multiple R, each of the multiple Rs independently represents a hydrogen atom, a _C1-6 haloalkyl group, a halogen atom, a cyano group, or a nitro group.
A method for producing a hydrazone derivative represented by the following formula:
The following formula (3):

[In the formula, _R3 , _R4 , X, _Y1 , _Y2 , _Y3 , _Y4 and n are as defined in the above formula (2).]
and a ketone derivative represented by the following formula (11):

[In the formula, _R1 is as defined in formula (2) above.]
The method includes reacting a hydrazine derivative represented by the formula: An agricultural and horticultural agent containing the hydrazone derivative or its salt according to any one of claims 1 to 2. An agricultural and horticultural nematode control agent containing the hydrazone derivative or its salt according to any one of claims 1 to 2. An agricultural and horticultural pest control agent containing the hydrazone derivative or its salt according to any one of claims 1 to 2. A method for controlling plant pests, comprising the step of treating pests and/or their habitat and/or seeds and/or plant propagation materials with the agricultural and horticultural agent according to claim 10. A method for preventing plant pests, comprising a step of treating a place where a useful crop is to be grown or where the useful crop is being grown, or the growing crop, with the agricultural and horticultural agent according to claim 10. A method for preparing an agrochemical composition, comprising the step of mixing the agricultural and horticultural agent according to claim 10 with a filler and/or a surfactant.