Novel hydrazone derivative and agent for agricultural and horticultural use containing same as active ingredient

Abstract

The present invention provides a compound which exhibits an excellent effect as an agent for agricultural and horticultural use, especially as a bactericide for agricultural and horticultural use.　The present invention provides, as an active ingredient, a hydrazone derivative which is represented by formula (1) or a salt thereof. In the formula, R1 represents a hydrogen atom, a C1-6 alkyl group, or the like; R2 represents a formyl group, or may form a group represented by formula (2) together with R1; and R5 represents OR6 or NR7R8, wherein R6 represents a C1-6 alkyl group, R7 represents a hydrogen atom or a C1-6 alkyl group, and R8 represents a C1-6 alkyl group, or may form a saturated 4-7 membered ring together with a nitrogen atom to which R7 and R8 are bonded.

Description

New hydrazone derivatives and agricultural and horticultural agents containing them as active ingredients

[0001] The present invention relates to novel hydrazone derivatives and agricultural and horticultural agents, particularly agricultural and horticultural pesticides or nematode control agents, containing said compounds as active ingredients, and methods of using them.

[0002] In the agricultural and horticultural fields, plant pesticides for controlling various pests have been developed and put to practical use. 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 discloses that semicarbazone derivatives are useful as agricultural insecticides. However, while Patent Document 1 discloses semicarbazone compounds, it does not disclose hydrazone compounds such as those of the present invention. Furthermore, Patent Document 1 does not disclose any effect on nematodes for the compounds disclosed therein. Patent Documents 2 and 3 describe compounds similar to the compounds of the present invention as agricultural nematode control agents, but do not disclose compounds in which an azole is bonded to the β-carbon of a phenylhydrazone such as those of the present invention. Furthermore, Patent Documents 4 and 5 disclose hydrazone compounds similar to the compounds of the present invention. However, these patent documents relate to compounds in which a phenyl group and a β-carbon of a phenylhydrazone are bonded to form a ring structure in the phenylhydrazone skeleton, and do not disclose compounds that do not have such a ring structure. Furthermore, Patent Document 6 discloses cyclic hydrazone compounds having, for example, 2,3,4,5-tetrahydro-1,2,4-triazine and 3,6-dihydro-2H-1,3,4-oxadiazine, etc. However, in compounds having these structures, the β-carbon of the phenylhydrazone forms a ring structure with the nitrogen atom of the hydrazone group, and does not disclose compounds that do not form such a ring.

[0003] Japanese Patent Application Laid-Open No. 8-073436 International Publication No. 2020 / 179910 International Publication No. 2023 / 282110 International Publication No. 01 / 36381 Japanese Patent Application Laid-Open No. 2002-155044 International Publication No. 93 / 19045

[0004] In agricultural and horticultural crop production, damage caused by pests and diseases remains significant, and the development of new agricultural and horticultural pesticides is desired due to factors such as the emergence of pests resistant to existing pesticides.

[0005] As a result of extensive research aimed at solving the above problems, the present inventors 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, particularly as an agricultural and horticultural pesticide or nematode control agent, and have thus completed the present invention.

[0006] [Wherein R represents a hydrogen atom, C 1-6 Alkyl group, C 2-6 Alkenyl group, C 2-6 R represents an alkynyl group or a benzyl group; R represents a formyl group; or R and R together represent the formula:

[0007] R5 represents OR6 or NR7R8, and R6 represents C 1-6 R represents a hydrogen atom or a C 1-6 represents an alkyl group, and R is C 1-6 R7 and R8 may be bonded to each other to form a saturated 4- to 7-membered ring together with the nitrogen atom to which they are bonded; R3 is C 1-6 R4 represents a hydrogen atom or a C 1-6 R3 and R4 together may form a (C3-C6)-carbocyclic ring, X is a hydrogen atom, C 1-6 Alkyl group, C 1-6 Haloalkyl group, C 1-6 Alkoxy group, C 1-6 represents a haloalkoxy group, a halogen atom, a cyano group, or a nitro group, and when there are a plurality of Xs, they may be the same or different from one another; n represents an integer of 1 to 5; Y1, Y2, Y3, and Y4 each independently represent a nitrogen atom or a CR group; R represents a hydrogen atom, a halogen atom, or a C 1-6 Alkyl group or C 1-6and when there are a plurality of R, they may be the same or different.] 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 the compound as an active ingredient, a method for using the same, and a method for producing the compound, etc.

[0008] Specifically, the present invention provides the following aspects: 1. A compound represented by the following formula (1):

[0009] [wherein R1 is a hydrogen atom, C 1-6 Alkyl group, C 2-6 Alkenyl group, C 2-6 R represents an alkynyl group or a benzyl group, R represents a formyl group, or R and R together represent the following formula:

[0010] R5 represents OR6 or NR7R8, and R6 represents C 1-6 R represents a hydrogen atom or a C 1-6 represents an alkyl group, and R is C 1-6 R7 and R8 may be bonded to each other and together with the nitrogen atom to which they are bonded form a saturated 4- to 7-membered ring, and R3 is C 1-6 R4 represents a hydrogen atom or a C 1-6 R3 and R4 together may form a (C3-C6)-carbocyclic ring, X is a hydrogen atom, C 1-6 Alkyl group, C 1-6 Haloalkyl group, C 1-6 Alkoxy group, C 1-6 represents a haloalkoxy group, a halogen atom, a cyano group, or a nitro group, and when there are a plurality of Xs, they may be the same or different from one another; n represents an integer of 1 to 5; Y1, Y2, Y3, and Y4 each independently represent a nitrogen atom or a CR group; R represents a hydrogen atom, a halogen atom, or a C 1-6 Alkyl group or C 1-6It is a haloalkyl group, and when there are a plurality of R, they may be the same or different.

[0011] 2. Y2 represents CR, and R represents C 1-6 2. A hydrazone derivative or a salt thereof according to the above item 1, wherein the hydrazone derivative represents a haloalkyl group. 3. A hydrazone derivative represented by the following formula (2):

[0012] [Wherein R represents a hydrogen atom, C 1-6 Alkyl group, C 2-6 Alkenyl group, C 2-6 R3 represents an alkynyl group or a benzyl group; 1-6 R4 represents a hydrogen atom or a C 1-6 R3 and R4 together may form a (C3-C6)-carbocyclic ring, X is a hydrogen atom, C 1-6 Alkyl group, C 1-6 Haloalkyl group, C 1-6 Alkoxy group, C 1-6 represents a haloalkoxy group, a halogen atom, a cyano group, or a nitro group, and when there are a plurality of Xs, they may be the same or different from one another; n represents an integer of 1 to 5; Y1, Y2, Y3, and Y4 each independently represent a nitrogen atom or a CR group; R represents a hydrogen atom, a halogen atom, or a C 1-6 Alkyl group or C 1-6 It represents a haloalkyl group, and when there are a plurality of R's, they may be the same or different from each other.] 4. A ketone derivative represented by the following formula (3):

[0013] wherein R is C 1-6 R4 represents a hydrogen atom or a C 1-6 R3 and R4 together may form a (C3-C6)-carbocyclic ring, X is a hydrogen atom, C 1-6 Alkyl group, C 1-6 Haloalkyl group, C 1-6 Alkoxy group, C 1-6represents a haloalkoxy group, a halogen atom, a cyano group, or a nitro group, and when there are a plurality of Xs, they may be the same or different from one another; n represents an integer of 1 to 5; Y1, Y2, Y3, and Y4 each independently represent a nitrogen atom or a CR group; R represents a hydrogen atom, a halogen atom, or a C 1-6 Alkyl group or C 1-6 represents a haloalkyl group, and when there are a plurality of R, they may be the same or different.

[0014] 5. The following formula (4),

[0015] [Wherein R represents a hydrogen atom, C 1-6 Alkyl group, C 2-6 Alkenyl group, C 2-6 R3 represents an alkynyl group or a benzyl group; 1-6 R4 represents a hydrogen atom or a C 1-6 R3 and R4 together may form a (C3-C6)-carbocyclic ring, X is a hydrogen atom, C 1-6 Alkyl group, C 1-6 Haloalkyl group, C 1-6 Alkoxy group, C 1-6 represents a haloalkoxy group, a halogen atom, a cyano group, or a nitro group, and when there are a plurality of Xs, they may be the same or different from one another; n represents an integer of 1 to 5; Y1, Y2, Y3, and Y4 each independently represent a nitrogen atom or a CR group; R represents a hydrogen atom, a halogen atom, or a C 1-6 Alkyl group or C 1-6 represents a haloalkyl group, and when there are a plurality of R, they may be the same or different from each other.]

[0016] [wherein R, R, R, X, Y, Y, Y, Y, and n are as defined in formula (4)], is reacted with formic acid and / or a hydrazone derivative represented by the following formula (5): HCOOR (5) [wherein R is C 1-6 6. A production method comprising reacting a compound represented by the following formula (6):

[0017] [Wherein R5 represents OR6 or NR7R8, R6 represents C 1-6 R represents a hydrogen atom or a C 1-6 represents an alkyl group, and R is C 1-6 R7 and R8 may be bonded to each other and together with the nitrogen atom to which R7 and R8 are bonded form a saturated 4- to 7-membered ring, R3 is C 1-6 R4 represents a hydrogen atom or a C 1-6 R3 and R4 together may form a (C3-C6)-carbocyclic ring, X is a hydrogen atom, C 1-6 Alkyl group, C 1-6 Haloalkyl group, C 1-6 Alkoxy group, C 1-6 represents a haloalkoxy group, a halogen atom, a cyano group, or a nitro group, and when there are a plurality of Xs, they may be the same or different from one another; n represents an integer of 1 to 5; Y1, Y2, Y3, and Y4 each independently represent a nitrogen atom or a CR group; R represents a hydrogen atom, a halogen atom, or a C 1-6 Alkyl group or C 1-6 represents a haloalkyl group, and when there are a plurality of R's, they may be the same or different from each other.]

[0018] [wherein R, R, X, Y, Y, Y, Y, and n are as defined in the above formula (6)],

[0019] [Wherein R5 is as defined in the above formula (6), R9 is C 1-6 7. A method for producing a compound represented by the following formula (9):

[0020] [wherein R7 is a hydrogen atom or C 1-6 represents an alkyl group, and R is C 1-6R7 and R8 may be bonded to each other and together with the nitrogen atom to which they are bonded form a saturated 4- to 7-membered ring, and R3 is C 1-6 R4 represents a hydrogen atom or a C 1-6 R3 and R4 together may form a (C3-C6)-carbocyclic ring, X is a hydrogen atom, C 1-6 Alkyl group, C 1-6 Haloalkyl group, C 1-6 Alkoxy group, C 1-6 represents a haloalkoxy group, a halogen atom, a cyano group, or a nitro group, and when there are a plurality of Xs, they may be the same or different from one another; n represents an integer of 1 to 5; Y1, Y2, Y3, and Y4 each independently represent a nitrogen atom or a CR group; R represents a hydrogen atom, a halogen atom, or a C 1-6 Alkyl group or C 1-6 and R represents a haloalkyl group, and when there are a plurality of R, they may be the same or different from each other.]

[0021] [In the formula, R, R, X, Y, Y, Y, Y, and n are as defined in the above formula (9), and R is C 1-6 represents an alkyl group.] to a hydrazone derivative represented by the following formula (11):

[0022] [wherein R7 and R8 are as defined in formula (9)]. 8. A production method comprising reacting an amine derivative represented by the following formula (4):

[0023] [Wherein R represents a hydrogen atom, C 1-6 Alkyl group, C 2-6 Alkenyl group, C 2-6 R3 represents an alkynyl group or a benzyl group; 1-6 R4 represents a hydrogen atom or a C 1-6 R3 and R4 together may form a (C3-C6)-carbocyclic ring, X is a hydrogen atom, C 1-6Alkyl group, C 1-6 Haloalkyl group, C 1-6 Alkoxy group, C 1-6 represents a haloalkoxy group, a halogen atom, a cyano group, or a nitro group, and when there are a plurality of Xs, they may be the same or different from one another; n represents an integer of 1 to 5; Y1, Y2, Y3, and Y4 each independently represent a nitrogen atom or a CR group; R represents a hydrogen atom, a halogen atom, or a C 1-6 Alkyl group or C 1-6 represents a haloalkyl group, and when there are a plurality of R, they may be the same or different from each other.]

[0024] [wherein R, R, X, Y, Y, Y, Y, and n are as defined in formula (4)],

[0025] [wherein R1 is as defined in the above formula (4), and Z represents a chlorine atom, a bromine atom, an iodine atom, a methanesulfonyloxy group, a p-toluenesulfonyloxy group, or a trifluoromethanesulfonyloxy group.] 9. A production method comprising reacting a compound represented by the following formula (2):

[0026] [Wherein R represents a hydrogen atom, C 1-6 Alkyl group, C 2-6 Alkenyl group, C 2-6 R3 represents an alkynyl group or a benzyl group; 1-6 R4 represents a hydrogen atom or a C 1-6 R3 and R4 together may form a (C3-C6)-carbocyclic ring, X is a hydrogen atom, C 1-6 Alkyl group, C 1-6 Haloalkyl group, C 1-6 Alkoxy group, C 1-6represents a haloalkoxy group, a halogen atom, a cyano group, or a nitro group, and when there are a plurality of Xs, they may be the same or different from one another; n represents an integer of 1 to 5; Y1, Y2, Y3, and Y4 each independently represent a nitrogen atom or a CR group; R represents a hydrogen atom, a halogen atom, or a C 1-6 Alkyl group or C 1-6 represents a haloalkyl group, and when there are a plurality of R, they may be the same or different from each other.]

[0027] [wherein R, R, X, Y, Y, Y, Y, and n are as defined in the above formula (2)],

[0028] [wherein R1 is as defined in formula (2) above.] 10. An agricultural and horticultural agent containing the hydrazone derivative or a salt thereof according to 1 or 2 above. 11. An agricultural and horticultural nematode control agent containing the hydrazone derivative or a salt thereof according to 1 or 2 above. 12. An agricultural and horticultural pest control agent containing the hydrazone derivative or a salt thereof according to 1 or 2 above. 13. A method for controlling plant pests, which comprises the step of treating pests and / or their habitats and / or seeds and / or plant propagation materials with the agricultural and horticultural agent according to 10 above. 14. A method for preventing plant pests, which comprises the step of treating a site where a useful crop is to be grown or is grown, or a crop that is growing, with the agricultural and horticultural agent according to 10 above. 15. A method for preparing an agricultural chemical composition, comprising the step of mixing the hydrazone derivative or its salt according to claim 1 or 2 with any one of a carrier, an emulsifier, a wetting agent, a dispersant and a disintegrant, or a combination of any of these.

[0029] The compounds of the present invention exhibit excellent effects as agricultural and horticultural agents, particularly as agricultural and horticultural pest control agents or nematode control agents.

[0030] In this specification, the term "halogen atom" refers to a chlorine atom, a bromine atom, an iodine atom, or a fluorine atom. 1-6The "alkyl group" is a straight-chain or branched-chain alkyl group, and suitable examples of such alkyl groups include methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, and isohexyl groups. The number of carbon atoms in the alkyl group is preferably 1 to 6, and more preferably 1 to 3. 2-6 The "alkenyl group" refers to a straight-chain or branched alkyl group containing one or more unsaturated double bonds between carbon-carbon bonds. Suitable examples of such alkenyl groups include vinyl, allyl, isopropenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1,1-dimethyl-2-propenyl, 1-ethyl-2-propenyl, 1-methyl-2-butenyl, 1-methyl-3-butenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1,1-dimethyl-2-butenyl, and 1,1-dimethyl-3-butenyl. The unsaturated double bond can be present at any position between the carbon-carbon bonds, and there may be one or more unsaturated double bonds. The alkenyl group has 2 to 6 carbon atoms, preferably 3 or 4 carbon atoms.

[0031] "C 2-6The "alkynyl group" refers to a straight-chain or branched-chain alkyl group containing one or more unsaturated triple bonds between carbon-atom bond bonds. Suitable examples of such alkynyl groups include 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 triple bond can be present at any position between the carbon-atom bond bonds, and the number thereof may be one or more. The alkynyl group has 2 to 6 carbon atoms, preferably 3 or 4 carbon atoms.

[0032] "C 1-6 The "haloalkyl group" is the same as the above "C 1-6 The haloalkyl group is a straight-chain or branched-chain alkyl group in which one or more carbon atoms of the "alkyl group" are substituted with the above-mentioned halogen atoms. Suitable examples of such haloalkyl groups include a fluoromethyl group, a chloromethyl group, a difluoromethyl group, a trifluoromethyl group, a chlorodifluoromethyl group, a bromodifluoromethyl group, a dichlorofluoromethyl group, a 1-fluoroethyl group, 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, and a nonafluorobutyl group. The haloalkyl group has 1 to 6 carbon atoms, and preferably 1 to 3 carbon atoms.

[0033] "C 1-6The "alkoxy group" is a straight-chain or branched-chain alkyl group bonded to an oxygen atom, and suitable examples of such an alkoxy group include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, a cyclopropyloxy group, an n-butoxy group, a sec-butoxy group, a tert-butoxy group, an n-pentoxy group, and an n-hexyloxy group. The number of carbon atoms in the alkoxy group is 1 to 6, and preferably 1 to 4. 1-6 A "haloalkoxy group" is an alkoxy group in which any carbon atom of the above alkoxy group is substituted with a halogen atom. Suitable examples of such haloalkoxy groups include fluoromethoxy, dichloromethoxy, trichloromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, dichlorofluoromethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2,2-trifluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 1-fluoroisopropoxy, 3-fluoropropoxy, 3-chloropropoxy, 3-bromopropoxy, 4-fluorobutoxy, and 4-chlorobutoxy. The haloalkoxy group has 1 to 6 carbon atoms, and preferably 1 to 3. Alternatively, the haloalkoxy group may be substituted with 1 to 9 halogen atoms.

[0034] "C 3-6 A "cycloalkyl group" is a cyclic alkyl group, and such a C 3-6 Suitable examples of the cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, etc. The number of carbon atoms in such a cycloalkyl group is preferably 3 to 6.

[0035] The benzyl group can be, for example, C 1-6 Alkyl groups, halogen atoms, C 1-6 Alkoxy group, C 1-6 Haloalkyl group, C 1-6 It may be substituted with a haloalkoxy group.

[0036] In the compounds described herein, R and R may be bonded to each other and together with the nitrogen atom to which they are bonded form a saturated 4- to 7-membered ring. Suitable examples of such saturated 4- to 7-membered rings include a pyrrolidine ring and a piperidine ring.

[0037] Examples of salts of the hydrazone derivatives represented by formula (1) of the present invention 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 compounds of the present invention may contain one or more asymmetric centers in their structural formulas, and may exist as two or more optical isomers and diastereomers. The present invention encompasses all of these optical isomers and mixtures containing these optical isomers in any proportion. Furthermore, the compounds 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 their structural formulas. The present invention encompasses all of these geometric isomers and mixtures containing these geometric isomers in any proportion. For example, in the compounds described herein, the wavy line in the structural formula means that any of the two or more geometric isomers derived from the carbon-carbon double bond or the carbon-nitrogen double bond is included.

[0038] In the hydrazone derivative represented by the formula (1) of the present invention, it is preferable that Y2 represents CR. In the hydrazone derivative represented by the formula (1) of the present invention, R represents C 1-6 In the hydrazone derivative represented by the formula (1) of the present invention, it is preferable that R3 represents a methyl group and R4 represents a hydrogen atom. It is also preferable that R3 and R4 represent methyl groups. In the hydrazone derivative represented by the formula (1) of the present invention, Y2 represents CR and R represents C 1-6 It is more preferred that Y represents a haloalkyl group, R represents a methyl group, and R represents a hydrogen atom. 1-6 More preferably, R3 and R4 represent a haloalkyl group, and R3 and R4 represent a methyl group.

[0039] Representative methods for producing the novel hydrazone derivative represented by the formula (1) of the present invention and its intermediates, the hydrazone derivative represented by the formula (2) and the ketone derivative represented by the formula (3), are shown below, but the methods for producing the above compounds in the present invention are not limited to these.

[0040] [Wherein, X, R3, R4, and n are as defined in the formula (1).] In the method shown in reaction scheme 1, when R4 is a hydrogen atom, the alcohol derivative represented by the formula (16) can be produced by reacting the ketone compound represented by the formula (15) with an aqueous formaldehyde solution in an inert solvent in the presence or absence of a base, in accordance with the method described in Journal of Organic Chemistry, Vol. 86, p. 6943 (2021), and when R4 is C 1-6 When the alkyl group is used, it can be produced by reacting the ketone compound represented by the formula (15) with paraformaldehyde in accordance with the method described in Organic Preparations and Procedures International, Vol. 21, p. 91 (1989).

[0041] [In the formula, L represents a chlorine atom, a bromine atom, a p-toluenesulfonyloxy group, or a methanesulfonyloxy group, and X, R3, R4, and n are as defined in formula (1).] In the method shown in reaction formula 2, the ketone derivative represented by formula (17) can be produced by reacting the ketone compound represented by formula (16) with a halogenating agent, p-toluenesulfonyl chloride, methanesulfonyl chloride, or the like in the presence or absence of a base.

[0042] A wide variety of known solvents can be used in the halogenation reaction or sulfonation reaction of the compound of formula (16), 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 as needed.

[0043] Known inorganic and organic bases can be used as the base in the sulfonate esterification reaction of the compound of formula (16). Examples of inorganic bases 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 organic bases 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 bases can typically be used in an amount of 1 to 100 equivalents relative to the ketone compound represented by formula (16).

[0044] Examples of halogenating agents used in the halogenation reaction of the ketone compound represented by formula (16) include chlorine, bromine, N-chlorosuccinimide, N-bromosuccinimide, thionyl chloride, sulfuryl chloride, phosphorus oxychloride, phosphorus tribromide, and phosphorus pentabromide. The reaction can usually be carried out at a temperature ranging 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 and other factors, but is generally complete 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 commonly used isolation methods, such as organic solvent extraction, chromatography, recrystallization, and distillation. Alternatively, the target compound can be used in the next reaction step without isolating it from the reaction system. Reaction Scheme 3

[0045] [In the formula, X, Y, Y, Y, Y, L, R, R, and n are as defined in the formulas (1) and (17).] In the method shown in Reaction Scheme 3, the ketone derivative represented by the formula (3) can be produced by reacting the ketone compound represented by the formula (17) with the azole compound of the formula (18) in an inert solvent in the presence or absence of a base.

[0046] A wide variety of known solvents can be used as the solvent for the reaction of the compound of formula (17) with the compound of formula (18), 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 as needed.

[0047] Known inorganic and organic bases can be used as the base used in the reaction of the compound of formula (17) with the compound of formula (18). Examples of inorganic bases 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 organic bases 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. Such bases can be used in an amount of typically 1 to 100 equivalents, preferably 1 to 2 equivalents, relative to the ketone compound represented by formula (17).

[0048] The ratio of the ketone compound represented by formula (17) to the azole compound represented by formula (18) is preferably 1 to 2 equivalents of compound (17). The reaction can usually be carried out at a temperature ranging 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 commonly used isolation means, such as organic solvent extraction, chromatography, recrystallization, distillation, etc. Reaction Scheme 4

[0049] [In the formula, X, Y1, Y2, Y3, Y4, R1, R3, R4 and n are as defined in the formula (1).] In the method shown in reaction formula 4, 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 of the formula (14) in an inert solvent in the presence or absence of an acid.

[0050] A wide variety of known solvents can be used in the reaction of the ketone derivative of formula (3) with the hydrazine compound of formula (14), as long as they are inert to the reaction. Examples of such solvents include alcohols such as methanol, ethanol, n-propanol, and isopropanol; 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 as needed. Known inorganic and organic acids can be used as the acid used in the reaction of the compound of formula (3) with 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.

[0051] The acid used in the reaction of the compound of formula (3) with the compound of formula (14) is typically 0.001 to 2 equivalents, preferably 0.01 to 1 equivalent, relative to the ketone compound of formula (3). The ratio of the ketone derivative of formula (3) to the hydrazine compound of formula (14) can be appropriately selected from a wide range. Preferably, the latter is used in an amount of 1 to 10 moles or more, more preferably 2.0 to 5.0 moles, per mole of the former. The reaction is preferably carried out at 0°C to the boiling point of the solvent used, more preferably at room temperature or under reflux. The reaction time varies depending on the reaction temperature, but is generally not universally specified. The reaction is generally completed within about 0.1 to 24 hours. After completion of the reaction, the target product can be isolated from the reaction system using conventional methods. The target product can be produced by purifying the product, if necessary, by recrystallization or column chromatography. Alternatively, the target product can be used in the next reaction step without isolating it from the reaction system. Reaction Scheme 5

[0052] [Wherein R9 is C 1-6 represents an alkyl group, and X, Y, Y, Y, Y, R, R, R and n are as defined in formula (1).] In the method shown in reaction formula 5, the hydrazone derivative represented by formula (4) can be produced by a formylation reaction between the hydrazone derivative represented by formula (2) and formic acid and / or the formic acid derivative represented by formula (5).

[0053] A wide variety of known solvents can be used in the formylation reaction of the hydrazone compound represented by formula (2), 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; 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 can be used alone or in combination as needed. Examples of formylating agents used in the formylation reaction of the hydrazone compound represented by formula (2) include formic acid, methyl formate, and ethyl formate. Such formylating agents can be used in an amount of typically 1 to 100 equivalents, preferably 1 to 10 equivalents, relative to the hydrazone derivative represented by formula (2). The reaction can usually be carried out at a temperature ranging from -78°C to the boiling point of the solvent used, preferably from 0°C to the boiling point. 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 compounds obtained in each of the above reactions can be easily isolated from the reaction mixture by commonly used isolation methods, such as organic solvent extraction, chromatography, recrystallization, and distillation. Reaction Scheme 6

[0054] [In the formula, X, Y1, Y2, Y3, Y4, R3, R4, R5, R9, and n are as defined in the formulas (1) and (5).] Specific embodiments of this reaction formula 6 include those shown in the following reaction formulas 7, 8, and 9. The compound defined by formula (7) is a compound in which R1 is a hydrogen atom in formula (2), which has already been explained. Reaction formula 7

[0055] [In the formula, X, Y, Y, Y, Y, R, R, R, and n are as defined in formula (1).] In the method shown in reaction formula 7, the hydrazone derivative represented by formula (10) can be produced by reacting the hydrazone derivative represented by formula (7) with an orthoformate ester (19).

[0056] A wide variety of known solvents can be used in the reaction between the hydrazone compound represented by formula (7) and the orthoformate represented by formula (19), 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; 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 can be used alone or in combination as needed.

[0057] Examples of the orthoformate (19) used in the imination reaction of the hydrazone compound represented by formula (7) include methyl orthoformate, ethyl orthoformate, propyl orthoformate, and butyl orthoformate. Such an orthoformate (19) can be used in an amount of typically 1 to 20 equivalents, preferably 2 to 10 equivalents, relative to the hydrazone derivative represented by formula (7). The reaction can be carried out at temperatures ranging from −78°C to the boiling point of the solvent used, preferably from 0°C to the boiling point. The reaction time varies depending on the reaction temperature, but is generally complete within approximately 0.1 to 24 hours. The target compound obtained in each of the above reactions can be easily isolated from the reaction mixture by commonly used isolation methods, such as organic solvent extraction, chromatography, recrystallization, and distillation. Reaction Scheme 8

[0058] [In the formula, X, Y, Y, Y, Y, R, R, R, R, R, and n are as defined in formula (1).] In the method shown in reaction formula 8, the hydrazone derivative represented by formula (9) can be produced by reacting the hydrazone derivative represented by formula (10) with the amine derivative represented by formula (11).

[0059] A wide variety of known solvents can be used in the amination reaction of the hydrazone compound represented by formula (10), 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; 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 can be used alone or in combination as needed. 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).

[0060] The reaction can usually be carried out within a temperature range from -78°C to the boiling point of the solvent used, and is preferably carried out at 0°C to the boiling point. The reaction time varies depending on the reaction temperature and other factors, 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 commonly used isolation means, such as organic solvent extraction, chromatography, recrystallization, distillation, etc. Reaction Scheme 9

[0061] [In the formula, X, Y, Y, Y, Y, R, R, R, R, R, and n are as defined in formula (1).] In the method shown in reaction formula 9, the hydrazone derivative represented by formula (9) can be produced by reacting the hydrazone derivative represented by formula (7) with an acetal derivative (20).

[0062] A wide variety of known solvents can be used in the reaction between the hydrazone compound represented by formula (7) and the acetal derivative represented by formula (20), 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; 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 can be used alone or in combination as needed. Examples of the acetal derivative (20) used in the imination reaction of the hydrazone compound represented by formula (7) include N,N-dimethylformamide dimethyl acetal. The acetal derivative (20) can be used in an amount of typically 1 to 10 equivalents, preferably 1 to 5 equivalents, relative to the hydrazone derivative represented by formula (7). The reaction can usually be carried out at a temperature ranging from -78°C to the boiling point of the solvent used, preferably from 0°C to the boiling point. 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 commonly used isolation methods, such as organic solvent extraction, chromatography, recrystallization, distillation, etc. Reaction Scheme 10

[0063] [In the formula, Z represents a chlorine atom, a bromine atom, an iodine atom, a methanesulfonyloxy group, a p-toluenesulfonyloxy group, or a trifluoromethanesulfonyloxy group; X, Y1, Y2, Y3, Y4, R3, R4, and n are as defined in formula (1); and R1 represents a substituent other than a hydrogen atom.] The compound defined by formula (12) is a compound in which R1 is a hydrogen atom in formula (4), the production method of which has already been explained. In the method shown in reaction formula 10, the hydrazone derivative represented by formula (4) can be produced by reacting the hydrazone derivative represented by formula (12) with an alkylating agent represented by formula (13) in an inert solvent in the presence or absence of a base.

[0064] A wide variety of known solvents can be used in the alkylation reaction of the hydrazone derivative represented by formula (12), 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; 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 can be used alone or in combination as needed. Examples of the alkylating agent (13) used in the alkylation reaction of the hydrazone compound represented by formula (12) include methyl iodide, ethyl iodide, and dimethyl sulfate. Such an alkylating agent can be used in an amount of typically 1 to 10 equivalents, preferably 1 to 3 equivalents, relative to the hydrazone derivative represented by formula (12). The reaction can typically be carried out at temperatures ranging from −78°C to the boiling point of the solvent used, preferably from 0°C to the boiling point. The reaction time varies depending on the reaction temperature and other factors, but is generally complete within approximately 0.1 to 24 hours. The target compound obtained in each of the above reactions can be easily isolated from the reaction mixture by commonly used isolation methods, such as organic solvent extraction, chromatography, recrystallization, and distillation.

[0065] Representative compounds of the hydrazone derivatives represented by the formula (1) are shown in Table 1, representative compounds of the hydrazone derivatives represented by the formula (2) are shown in Table 2, representative compounds of the ketone derivatives represented by the formula (3) are shown in Table 3, representative compounds of the ketone derivatives represented by the formula (16) are shown in Table 4, and representative compounds of the ketone derivatives represented by the formula (17) are shown in Table 5, but the scope of the present invention is not limited to these compounds. In Tables 1 to 5, physical properties are shown as properties or melting points (°C), "Me" represents a methyl group, "Et" represents an ethyl group, "i-Pr" represents an isopropyl group, and "Bn" represents a benzyl group. General Formula (1)

[0066] General formula (2)

[0067] General formula (3)

[0068] General formula (16)

[0069] General formula (17)

[0070]

[0071] The compound of the present invention can be used for the prevention and extermination of organisms that are harmful to livestock in various situations, such as agriculture, indoors or in forests, or in terms of hygiene. Specific use situations, target pests, and use methods are shown below, but the scope of the present invention is not limited by these use situations, target pests, and use methods. The compound of the present invention represented by the formula (1) can be used to prevent or exterminate agricultural crops, for example, food crops (rice, barley, wheat, rye, oats, and other wheat varieties, corn, potato, sweet potato, taro, soybean, adzuki bean, broad bean, pea, kidney bean, peanut, and other legumes), vegetables (cruciferous crops such as cabbage, Chinese cabbage, radish, turnip, broccoli, cauliflower, and komatsuna, pumpkin, cucumber, etc.), and the like. , watermelon, melon, and other cucumbers, eggplant, tomato, bell pepper, pepper, okra, spinach, lettuce, lotus root, carrot, burdock, garlic, onion, green onion, and other alliums), mushrooms (shiitake, mushrooms, etc.), fruit trees and fruits (apples, citrus fruits, pears, grapes, peaches, plums, cherries, walnuts, chestnuts, almonds, bananas, strawberries, etc.), flavorings, etc. It can also be used to control pests such as arthropods, mollusks, nematodes, fungi (e.g., Myxomycota, Myxomycota, Bacteria, Actinomycetes), and bacteria that damage ornamental crops (e.g., lavender, rosemary, thyme, parsley, pepper, ginger), specialty crops (e.g., tobacco, tea, sugar beet, sugarcane, hops, cotton, hemp, olive, rubber, coffee), pasture and forage crops (e.g., timothy, clover, alfalfa, corn, sorghum, orchardgrass, grasses, legumes), turfgrass (e.g., Korean grass, bentgrass), forest trees (e.g., Abies sachalinensis, Ezo spruce, pines, hiba, cedar, cypress), and ornamental plants (e.g., herbaceous and flowering plants such as chrysanthemums, roses, carnations, and orchids, and garden trees such as ginkgo, cherry trees, and Japanese maples). Specific pests include the following:

[0072] 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 of the family Yponomeutidae; xylostella), etc., Tortricidae such as the smaller apple tortrix moth (Adoxophyes orana fasciata), the smaller tea tortrix moth (Adoxophyes honmai), the midden tea tortrix moth (Archips fuscocupreanus), the tea tortrix moth (Homona magnanima), the tea leaf moth (Caloptilia theivora), the pear fruit moth (Grapholita molesta), etc., and Psychidae such as Eumeta minuscula, etc.

[0073] Lyonetia prunifoliella malinella, Lyonetia clerkella, etc., of the Agrominidae family; Phyllocnistis citrella, etc., of the Licoriceae family; Phyllonorycter ringoniella, etc., of the Gracilariae family; Acrolepiopsis sapporensis, etc., of the Agrominidae family; Synanthedin hector, etc., of the Clearwing family; and Stathampoda, masinissa, etc., Gelechiidae: Pectinophora gossypiella, etc., Scutellaridae: Carposina niponensis, etc., Scutellaridae: Cossus jezoensis, etc., Scutellaridae: Nemapogon granella, etc., Scutellaridae: Monema flavecens, Parasa lepida, Scopelodes contracus, etc., Crambidae: Chilo suppressalis, etc. suppressalis), Scirpophaga incertulas, Cnaphalocrocis medinalis, Hellulla undalis, Conogethes punctiferlis,

[0074] Diaphania indica, Parapediasia teterrella, etc., Locastra muscosalis, etc. of the Pyralidae family, Parnara guttata, etc. of the Hesperiidae family, Papilio xuthus, etc. of the Papilionidae family, Pieris rapae crucivora, etc. of the Pieridae family, Lampides boeticus, etc. of the Lycaenidae family, Ascotis, etc. of the Geometridae family selenaria, etc., Sphingidae: Agrius convolvuli, etc., Donatella flavescens, etc., Lascivious moth: Malacosoma neustrium testaceum, etc., Lascivious moth: Saturnia japonica, etc., Lymantriidae: Eupproctis pseudoconspersa, Orgyia thyellina, Telochurus recens, etc. adults, larvae and eggs of the Arctiidae family such as Spilosoma imparilis and Hyphantria cunea, grapeberry moss (Endopiza viteana), codling moth (Laspeyresia pomonella), etc.;

[0075] Coleoptera, for example, Anomala cuprea, Popillia japonica, Oxycetonia jucunda, Anomala geniculata, etc. of the Scarabaeidae family, Agrilus auriventris, etc. of the Buprestidae family, Melanotus fortnumi, etc. of the Elateridae family, Epilachna 24-spotted ladybird beetle, vigintioctopunctata, etc., the Cerambycidae family, such as the spotted longhorn beetle (Anoplophora malasiaca) and the grape tiger longhorn beetle (Xylotrechus pyrrhoderus), and the Chrysomelidae family, such as the cucumber beetle (Aulacophora femoralis), rootworm species (Diabrotica spp.), the striped flea beetle (Phyllotreta striolata), the tortoise beetle (Cassida nebulosa), the radish beetle (Phaedon brassicae), the rice leaf beetle (Oulema oryzae), and the Mexican beetle (Epilachna varivestis), Colorado potato beetle (Leptinotarsa ​​decemlineata), etc., peach vest weevil (Rhynchites heros) etc. of the family Alaridae, sweet potato weevil (Cylas formicarius) etc. of the family Curculionidae, chestnut weevil (Curculio sikkimensis), rice water weevil (Lissorhoptrus oryzophilus), boll weevil (Anthonomus gradis grandis), grass weevil (Sphenophrus venatus) etc. adults, larvae and eggs of the Nitidulidae family, such as Epuraea domina;

[0076] Heteroptera of the Hemiptera order, for example, Eurydema rugosum, Eysarcoris lewisi, Eysarcoris parvus, Nezara viridula, Plautia stalii, Halymorpha mista, etc. of the Hemiptera family, Urochela luteovoria, etc. of the Lygaeidae family, Togo stink bug, etc. hemipterus, etc., of the Coreidae family, the narrow-legged stink bug (Riptortus clavatus), the narrow-legged stink bug (Cletus punctiger), etc., of the Riceidae family, the spider stink bug (Leptocorisa chinensis), etc., of the Pyrrhocoridae family, the red-spotted stink bug (Dysdeercus cingulatus), etc., of the Tingidae family, the pear-leaved stink bug (Stephanitis nashi), the azalea stink bug (Stephanitis pyrioides), etc., of the Miridae family, the light-striped mist bug (Apolygus spinolai), the red-striped mist bug (Stenotus adults, larvae and eggs of the stink bug (Megacopta punctatissimum) of the family Bruchidae;

[0077] Homoptera of the Hemiptera order, for example, Platypleura kaempferi of the Cicadidae family, Arboria apicalis, Empoasca onukii, Nephotettix cincticeps, Nephotettix virescens of the Cicadellidae family, Laodelphax striatellus, Nilaparvata lugens, Sogatella furcifera of the Delphacidae family, furcifera, etc., Geisha distinctisima, etc. of the Psyllidae family, Psylla pyrisuga, Diaphorina citri, etc. of the Psyllidae family, Aleurocanthus spiniferus, Bemisia argentifolii, various biotypes of Bemisia tabaci, Dialeurodes citri, Trialeurodes trialeurodes, etc. of the Aleyrodidae family, vaporariorum), etc., Phylloxeridae family grape aphid (Viteus vitifolii), etc., Aphididae family Spiraea aphid (Aphis citricola), bean aphid (Aphis craccivora), cotton aphid (Aphis gossypii), potato aphid (Aulacorthum solani), radish aphid (Brevicoryne brassicae), citrus aphid (Toxoptera aurantii), citrus black aphid (Toxoptera citricidus), elderberry aphid (Aulacorthum magnoliae), pear aphid (Schizaphis piricola), green pear aphid (Nippolachnus piri), false radish aphid (Lipaphis erysimi), peach buttercup aphid (Hyalopterus pruni),Chrysanthemum aphid (Pleotrichophorus chrysanthemi), chrysanthemum long-horned aphid (Macrosiphoniella sanborni), broad bean long-horned aphid (Megoura crassicauda), thorn aphid (Sitobion ibarae),

[0078] Tulip aphid (Macrosiphum euphorbiae), Japanese burdock aphid (Myzus varians), green peach aphid (Myzus persicae), red-veined aphid (Rhopalosiphum rufiabdominalis), wheat neck aphid (Rhopalosiphum padi), wheat long-vein aphid (Sitobion akebiae), apple aphid (Eriosoma lanigerum), etc., Icerya purchasi of the family Coccidae, mulberry mealybug (Pseudococcus spp.) of the family Pseudococcidae, comstocki), citrus mealybug (Phenacoccus viburnae), Fuji mealybug (Phenacoccus kraunhiae), etc., the family Coccidae, such as the horned scale (Ceroplastes ceriferus) and the ruby ​​scale (Ceroplastes rubens), and the family Coccidae, such as the red scale (Aonidiella aurantii), the pear scale (Comstockasspis perniciosa), the white mulberry scale (Pseudaulacasspis pentagoa), and the Yanone scale (Unaspis Adults, larvae and eggs of P. yanonensis and the like;

[0079] Thysanoptera, for example, Scirtothrips dorsalis, Thrips palmi, Thrips tabaci, Thrips setosus, Frankliniella intonsa, Frankliniella occidentalis, Heliothrips japonica, and the like of the Thysanoptera family. haemorrhoidalis, etc., adults, larvae and eggs of the Ponticulothrips family, such as the rice thrips (Ponticulothrips diospyrosi) and rice thrips (Haplothrips aculeatus); Hymenoptera, for example, Athalia rosae rficornis and Arge pagana of the Tenthredinidae family, Arge mali of the Lamium family, and Dryocsmus gall wasp of the Cynipidae family. Adults, larvae and eggs of the Megachile family, such as the Rose Megachile (Megachile nipponica nipponica), and the Formicidae, such as the Black Mountain Ant (Formica japonica), the Giant Carpenter Ant (Camponotus kiusiuensis), the Black Wood Ant (Lasius fuliginosus), and the Fire Ant (Solenopsis richteri, S. invicta, S. geminata);

[0080] Diptera, for example, the soybean pod gall midge (Asphondylia yushimai) of the Cecidomyiidae family, the cherry fruit fly (Rhacochlaena japonica) and the melon fly (Bactrocera cucurbitae) of the Tephritidae family, the rice leaf fly (Hydrellia griseola) of the Rhizobidae family, the Drosophilidae fruit fly (Drosophila suzukii) of the Drosophilidae family, the bean leaf miner (Liriomyza trifolii) and the tomato leaf miner (Liriomyza sativae), Chromatomyia horticola, rice leafminer (Agromyza oryzae), eggplant leafminer (Liriomyza bryoniae), etc., seed gnats (Delia platura), onion gnats (Delia antiqua), etc. of the Anthomyiidae family; Orthoptera, for example, Locusta migratoria of the Grasshopper family, Ruspolia lineosa of the Tettigoniidae family, etc., Teleogryllus emma of the Gryllidae family, green tree crickets (Truljalia Adults, larvae and eggs of the order Isoptera, for example, adults, larvae and eggs of the family Termitidae, such as the grasshopper (Gryllotalpa orientalis), and adults, larvae and eggs of the family Acrididae, such as the grasshopper (Oxya yezoensis); Adults, larvae and eggs of the order Dermaptera, for example, adults, larvae and eggs of the family Dermaptidae, such as the earwig (Labidura riparia);

[0081] The order Collembola of the class Insecta of the phylum Arthropoda, for example, adults, larvae, and eggs of the yellow springtail (Sminthurus viridis) of the family Collembola, and the Matsumoto white springtail (Onychiurus matsumotoi) of the family Collembola; the order Isopada of the class Malacostraca of the phylum Arthropoda, for example, adults, larvae, and eggs of the Armadillidium vulgare of the family Armadillididae; the order Acari of the class Arachnida, for example, Polyphagotarsonemus latus and Phytonemus cyclamen of the family Tarsoridae pallidus, etc., Penthaleus major, etc., of the family Tetranychidae; Brevipalpus lewisi, Brevipalpus phoenicis, etc., of the family Tetranychidae; Panonychus citri, Panonychus ulmi, Tetranychus urticae, Tetranychus kanzawai, Amphitetranychus viennensis, Oligonychus ununguis, Bryobia, etc., of the family Tetranychidae. eharai), Miyake spider mite (Eotetranychus kankitus), clover spider mite (Bryobia praetiosa), etc., as well as the 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., adults, larvae and eggs of Tyrophagus putrescentiae and Rhizoglyphus robini of the Acaridae family;

[0082] Mollusca Gastropoda Primitive Glulagus (Architaenioglossa), for example, Pomacea canaliculata of the family Ponticidae, Pulmonata (Plumonata), for example, Achatina fulica of the family Achatidae, Meghimatium bilineatum of the family Slug, Milax gagates of the family Slug, Lehmannina valentiana of the family Slug, Acusta despecta sieboldiana of the family Snail, etc.; Tylenchida of the phylum Nematoda, class Phantomthia, for example, Ditylenchus destructor of the Anguinidae family, Tylenchorhynchus claytoni of the Tylencorhynchidae family, Pratylenchus penetrans and Pratylenchus coffeae of the Pratylenchidae family, Helicotylenchus dihystera of the Hoplolimidae family, Globodera potato cyst nematode of the Heterodera family, rostochiensis, etc., Meloidogyneaceae family's sweet potato root-knot nematode (Meloidogyne incognita), etc., Criconema jaejuense, etc., Anguinaceae family's strawberry root nematode (Nothotylenchus acris), etc., Aphelecchoides family's strawberry nematode (Aphelecchoides fragariae), etc.; Urodela class's Dorilamidae order, for example, Longidoridae family's large spur nematode (Xiphonema sp.), Trichodoridae family's spur nematode (Trichodorus sp.), etc.; Fungi and bacteria such as Eumycota, Myxomycota, Bacteriomycota, and Actinomycota.

[0083] Specific examples of diseases to which the compound of the present invention represented by the formula (1) can be applied include rice blast (Pyricularia oryzae), southern leaf blight (Cochliobolus miyabeanus), sheath blight (Rhizoctonia solani), lemma browning (Pantoea ananatis), brown stripe (Acidovorax avenae subsp. avenae), leaf sheath browning (Pseudomonas fuscovaginae), bacterial leaf blight (Xanthomonas oryzae pv. oryzae), bacterial damping-off (Burkholderia plantarii), and the like; graminis), Gibberella zeae, Puccinia striiformis, P. graminis, P. recondita, P. hordei, snow rot (Typhula sp., Micronectriella nivalis), Ustilago tritici, U. nuda, Tilletia caries, Pseudocercosporella herpotrichoides), rhynchosporium secalis, septoria leaf blight tritici), leaf spot (Leptosphaeria nodorum), net spot (Pyrenophora teres), hail disease (Helminthosporium zonatum Ikata), black node disease (Pseudomonas syringae pv. japonica), etc.; citrus black spot (Diaporthe citri), scab (Elsinoe fawcetti), fruit rot (Penicillium digitatum, P. italicum), brown rot (Phytophthora citrophthora, P. nicotianae), black spot (Phyllosticta Monilinia mali of apple,

[0084] Canker (Valsa mali), powdery mildew (Podosphaera leucotricha), leaf spot (Alternaria mali), black spot (Venturia inaequalis), black spot (Mycospherella pomi), anthracnose (Colletotrichum acutatum), ring spot (Botryosphaeria berengeriana), red spot (Gymnosporangium yamadae), brown spot (Monilinia fructicola), etc.; black spot of pear (Venturia nashicola, V. pirina), black spot (Alternaria Kikuchiana), red rot (Gymnosporangium haraeanum), brown rot (Monilinia fructigena), etc.; peach brown rot (Monilinia fructicola), black rot (Cladosporium carpophilum), Phomopsis rot (Phomopsis sp.), bacterial perforation 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), brown rot (Monilinia fructigena), black scab (Cladosporium viticolum), gray mold (Botrytis cinerea), crown gall bacterial disease (Agrobacterium vitis), etc.; persimmon anthracnose (Gloeosporium kaki), leaf drop (Cercospora kaki, Mycoshaerella nawae), etc.;Cucumber anthracnose (Colletotrichum lagenarium), powdery mildew (Sphaerotheca fuliginea, Oidiopsis taurica), vine wilt (Didymella bryoniae), vine wilt (Fusarium oxysporum), downy mildew (Pseudoperonospora cubensis), late blight (Phytophthora sp.), seedling damping-off (Pythium sp.), etc.; cucumber bacterial spot (Pseudomonas syringae pv. lochrymans), bacterial edge rot (Pseudomonas viridiflava), brown spot bacterial disease (Xanthomonas campestris pv. cucurbitae), etc.; melon brown spot bacterial disease (Xanthomonas campestris pv. cucurbitae), hairy root disease (Agrobacterium rhizogens), canker disease (Streptomyces sp.), etc.; watermelon fruit spot bacterial disease (Acidovorax avenae pv. citrulli), etc.; solanaceous vegetable bacterial wilt (Ralstonia solanacearum), etc.; tomato ring spot disease (Alternaria solani), leaf mold disease (Cladosporium fulvum), Phytophthora infestans, canker disease (Clavibacter michiganense subsp. michiganense);

[0085] Stem necrosis (Pseudomonas corrugata), soft rot (Pectobacterium carotovorum subsp. carotovorum), etc.; eggplant brown spot (Phomopsis vexans), powdery mildew (Erysiphe cichoracearum), etc.; cruciferous vegetables black spot (Alternaria japonica), white spot (Cercosporella brassicae), soft rot (Pectobacterium carotovorum subsp. carotovorum), etc.; cabbage rot (Pseudomonas syringae) pv. marginalis), black rot (Xanthomonas campestris pv. campestris), etc.; lettuce rot (Pseudomonas cichorii, Pseudomonas viridiflava), bacterial spot (Xanthomonas campestris pv. vitians), onion rust (Puccinia allii), etc.; soybean purple spot (Cercospora kikuchii), black rot (Elsinoe glycines), black spot (Diaporthe phaseolorum var. sojae), etc.; kidney bean anthracnose (Colletotrichum lindemthianum), etc.; peanut black spot (Cercospora personata), brown spot (Cercospora arachidicola), etc.; pea powdery mildew (Erysiphe pisi), etc.; potato summer blight (Alternaria solani), late blight (Phytophthora infestans), leaf rot fungus (Rhizoctonia solani), etc.; strawberry powdery mildew (Sphaerotheca humuli), etc.; tea net blight (Exobasidium reticulatum), Elsinoe leucospila, Pseudomonas syringae pv. theae, canker disease (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), cavity disease (Pectobacterium carotovorum subsp. carotovorum), etc.; sugar beet brown spot (Cercospora beticola), seedling damping-off (Aphanomyces cochliodes), etc.;

[0086] 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.; gray mold (Botrytis cinerea) and sclerotinia rot (Sclerotinia sclerotiorum) of various crops such as eggplant, cucumber, and lettuce; snow mold of turf (Pythium iwayamai, Tyohula incarnate, Fusarium nivale, Sclerotinia borealis), powdery mildew (Erysiphe graminis), frying disease (Lycoperdon perlatum, Lepista subnudo, Marasmius oreades), pseudoleaf 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.; red blight of bentgrass (Pythium aphanidermatum) and anthracnose (Colletotrichum sp.).

[0087] The compound of the present invention represented by the formula (1) can be used to control arthropods and fungi that are active indoors in buildings including ordinary houses and that damage or decay wood and its processed 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 and Reticulitermes speratus of the Rhinotermitidae family, other Reticulitermes genus termites (Reticulitermes hesperus, R. tibialis, R. flavipes, R. lucifugus, R. santonensis, etc.), Incisitermes minor, Odontotermes formosanus of the Termitidae family, and Hodotermopsis of the Pteromidae family. jzponica, adults, larvae and eggs of the domestic termite (Cryptotermes domesticus) of the family Isotermes;Coleoptera, for example, the rice weevil (Sitophilus zeamais) and the rice weevil (Sitophilus zeamais) of the Curculionidae family; the azuki bean weevil (Callosobruchus chinensis), the pea weevil (Bruchus pisorum), the broad bean weevil (Bruchus rufimanus) of the Bruchidae family; the red flour beetle (Tribolium castaneum) and the flat-headed red flour beetle (Tribolium confusum) of the Tenebrionidae family; the saw-toothed flat flour beetle (Oryzaephilus surinamensis), Cryptolestes pusillus, etc., Lasioderma serricorne, Stegobium paniceum, etc. from the Anobiidae family, Attagenus unicolor japonicus, Anthrenus verbasci, Dermestes maculatus, etc., Gibbium japonica ... aequinoctiale), etc., Dinoderus minutus of the Bostrichidae family, Rhizopertha dominica, etc., Lyctus brunneus of the Lyctidae family, etc. adults, larvae and eggs;

[0088] Lepidoptera, for example, adults, larvae and eggs of Cadra cautella, Ephestia kuehniella, Plodia interpunctella of the Pyralidae family, Sitotroga cerealella of the Gelechiidae family, Tinea translucens, Tineola bisselliella of the Tineidae family, etc.; Psosociidae, for example, Lepinotus reticulatus of the Liposcotidae family, Liposcelis adults, larvae and eggs of the order Blattola, for example, the German cockroach (Blattella germanica) of the family Blattidae, and adults, larvae and eggs of the family Blattidae, such as the Siberian cockroach (Periplaneta fuliginosa) and the Japanese cockroach (Periplaneta japonica); adults, larvae and eggs of the order Hymenoptera, for example, the house ant (Monomorium pharaoni) and the Japanese black ant (Monomorium nipponense) of the family Formicidae;

[0089] Thymidia, for example, adults, larvae and eggs of the family Thimpinae, such as Ctenolepisma villosa and Lepisma saccharina; Diptera, for example, adults, larvae and eggs of the family Drosophilidae, such as Drosophila melanogaster, and adults, larvae and eggs of the family Piophila casei; Arthropoda, Arachnida, for example, adults, larvae and eggs of the family Astigmatidae, such as Tyrophagus putrescentiae and Lardoglyphus konoi, and adults, larvae and eggs of the family Carpoglyphus. lactis), etc.; wood-rotting fungi such as Tyromyces palustris and Coriolus versicolor; material-deteriorating microorganisms such as Aspergillus niger, Aspergillus terreus, Aureobasidium pullulans, Chaetomium globosum, Cladosporium cladosporioides, Eurotium tonophilus, Fusarium moniliforme, Gliocladium virens, Myrothecium verrucaria, and Penicillium citrinum, Penicillium funiculosum, Rhizopus oryzae, etc.

[0090] The compound of the present invention represented by the formula (1) can also be used to control pests that harm or weaken trees in natural forests, artificial forests, and urban green spaces. Specific pests include the following:

[0091] Lepidoptera of the class Insecta of the phylum Arthropoda, for example, Calliteara argentata, Eupproctis pseudoconspersa, Orygia recens approximans, Eupproctis subflava, Lymantria dispar, etc. of the family Lymantriidae; Malacosoma nesutria testacea, Dendrolimus spectabilis, Dendrolimus tsuga, etc. of the family Lasiocampidae; superans, etc., of the Pyralidae family, the larch moth (Crytoblabes loxiella), etc., of the Noctuidae family, the turnip moth (Agrotis segetum), etc., of the Tortricidae family, the larch thread moth (Ptycholoma lecheana circumclusana), the chestnut moth (Cydia kurokoi), the Japanese cedar moth (Cydia cryptomeriae), etc., of the Arctiidae family, the mulberry fall webworm (Spilosoma imparilis), the American fall webworm (Hyphantria cunea), etc., of the Stigmella family, castanopsiella), etc., adults, larvae and eggs of the Limacodidae family such as Parasa lepida, Scopelodes contracus, and Microleon longipalpis;Coleoptera, for example, the family Scarabaeidae, such as the Japanese scarab beetle (Anomala rufocuprea) and the long-legged scarab beetle (Heptophylla picea), the family Buprestidae, such as the Zelkova long-legged ash borer (Agrilus spinipennis), the family Cerambycidae, such as the Japanese pine sawyer beetle (Monochamus alternatus), the family Chrysomelidae, such as the cedar leaf beetle (Basilepta pallidula), the family Curculionidae, such as the rust gourd weevil (Scepticus griseus) and the white-spotted pine weevil (Shirahoshizo insidiosus), etc., the giant weevil (Sipalinus gigas) of the Rhododendron family, the pine bark beetle (Tomicus piniperda) and the stag beetle (Indocryphalus aceris) of the Scolytidae family, and adults, larvae and eggs of the rice boston beetle (Rhizopertha dominica) of the Bostrichidae family;

[0092] Hemiptera, for example, adults, larvae and eggs of the Aphididae family such as the Japanese spruce aphid (Cinara todocola), the Aphididae family such as the Japanese spruce aphid (Adelges japonicus), the Diaphididae family such as the Japanese cedar scale (Aspidiotus cryptomeriae), the Coccidae family such as the Japanese cedar scale (Ceroplastes ceriferus); Hymenoptera, for example, adults, larvae and eggs of the Sawfly family such as the Japanese larch sawfly (Pachynematus itoi), the Pine sawfly (Neodiprion sertifer), the Chestnut gall wasp (Dryocosmus serrata), the Cynipidae family such as the Japanese chestnut gall wasp (Dryocosmus serrata). adults, larvae and eggs of the Diptera, for example, Tipula aino of the Crane Fly family, Strobilomyia laricicola of the Anthomyiidae family, and Contarinia inouyei and Contarinia matsusintome of the Cecidomyiidae family; adults, larvae and eggs of the Arthropoda, Arachnida class, and Acari, for example, Oligonichus hondoensis and Oligonichus ununguis; Phylum Nematoda, Class Phantomthia, Order Tylenchidae, for example, Bursaphelenchus xylophilus of the family Parasitaphelenchidae.

[0093] The compound of the present invention represented by formula (1) can also be used to prevent, treat, or control arthropods, nematodes, trematodes, cestodes, and protozoa that parasitize internally or externally in vertebrates, particularly warm-blooded vertebrates such as livestock and pets, such as cattle, 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 pests include the following:

[0094] Diptera of the class Insecta of the phylum Arthropoda, for example, Tabanus rufidens, Tabanus chrysurus, etc. of the family Tabanidae, Musca bezzii, Musca domestica, Stomoxys calcitrans, etc. of the family Muscidae, Gasterophilus intestinalis, etc. of the family Bosomidae, Hypoderma bovis, etc. of the family Bosomidae, Oestrus ovis, etc. of the family Oestrus, Aldrichina japonica, etc. of the family Calliphoridae grahami, etc., Phoridae family, Megaseria spiralis, etc., Sepsis punctum, etc., Zygophaga family, Telmatoscopus albipunctatus, Psychoda alternata, etc., Culex pipiens molestus, Culex pipiens pallens, Anopheles sinensis, Culex pipiens triaeniorhynchus, etc., of Culicidae family, Adults, larvae and eggs of the order Siphonaptera, for example, adults, larvae and eggs of the family Pulex irritans and dog fleas (Ctenocephalides canis) of the family Phlebotomidae;

[0095] Adults, larvae and eggs of the order Phthiraptera, for example, pig lice (Haematopinidae suis) and cow lice (Haematopinidae eurysternus) of the family Coccidae, horse lice (Damalinia bovis) of the family Coccidae, cow lice (Linognathus vituli) of the family Coccidae, chicken lice (Menopon gallinae) of the family Coccidae; adults, larvae and eggs of the order Arachnida, for example, Varroa jacobsoni of the family Varroa destructor, Haemaphysalis longicornis of the family Ixodidae longicornis), Ixodes ovatus, Boophilus microplus, Amblyomma testudinarium, etc., Ornithonyssus sylviarum, etc. of the family Ornithonyssidae, Dermanyssus gallinae, etc. of the family Miteidae, Demodex phylloides, etc. of the family Demodex mites, Sarcoptes scabiei bovis, Knemidocoptes scabiei, etc. of the family Sarcoptes adults, larvae and eggs of Otodectes mutans, etc., of the family Otodectes, such as Otodectes cynotis and Psoroptes communis; Strongyloides of the class Digenea of ​​the phylum Nematoda, such as bovine hookworm, pig kidney worm, pig lungworm, Trichostrongylus stercoralis, and bovine enterostigmata;

[0096] Ascarids, such as Ascaris suum and Ascaris avium; Platyhelminthes, Trematoda, such as Schistosoma japonicum, Hepatic fluke, Flaccidus amphistome, Paragonimus westermani, and Paragonimus ovalis; Cestoda, such as Tapeworm lamellar, Tapeworm dilatatus, Tapeworm benedensis, Tapeworm quadratus, Tapeworm spurtata, and Tapeworm ringworm; Protozoa, Flagellates, Rhizoflagellates, such as Histomonas; Promastigote, such as Leishmania and Trypanosoma; Multiflagellates, such as Giardia; Trichomonads, such as Trichomonas; Sarcoplasma, such as Entamoeba; The subclass Piroplasma of the class Sporozoa, for example, Theilaria, Babesia, etc.; the subclass Otosporozoa, for example, Eimeria, Plasmodium, Toxoplasma, etc.

[0097] The compound of the present invention represented by the formula (1) can be used to exterminate pests that directly harm or cause discomfort to humans, or to maintain public health against pests that carry or transmit pathogens. Specific pests include the following: Lepidoptera of the class Insecta of the phylum Arthropoda, for example, adults, larvae and eggs of the family Lymantriidae, such as Sphrageidus similis, the family Lasiocampidae, such as Kunugia undans, the family Lasiocampidae, such as Parasa consocia, the family Limacodidae, and adults, larvae and eggs of the family Zygaenidae, such as Artona martini; Coleoptera, for example, the family Xanthochroa waterhousei, the family Cerambycidae, such as Epicauta gorhani, the family Meloidae, and adults, larvae and eggs of the family Staphylinidae, such as Paederus sieboldii, the family Staphylinidae, and adults, larvae and eggs of the family Staphylinidae, such as Xanthochroa waterhousei, the family Cerambycidae, and adults, larvae and eggs of the family Staphylinidae, such as Xanthochroa sieboldii, the family Meloidae, and adults, larvae and eggs of the family Staphylinidae, such as Paederus sieboldii, the family Staphylinidae, and adults, larvae and eggs of the family Staphylinidae, such as Xanthochroa ... adults, larvae and eggs of the order Hymenoptera, for example, the yellow hornet (Vespa simillima xanthoptera) of the family Vespidae, the giant fire ant (Brachyponera chinensis) of the family Formicidae, and the yellow-striped firefly (Batozonellus annulatus) of the family Bambusophidae; ...

[0098] Diptera, for example, Culicidae, such as Armigeres subalbatus, Ceratopogonidae, such as Culicoides nipponensis, Ceratopogonidae, such as Chironomidae, Chironomus yoshimatsui, Ceratopogonidae, such as Simulium nikkoense, Tabanidae, such as Hirosia humilis, Musca domestica, Musca domestica, Ichneumonidae, such as Fannia canicularis, Calliphoridae, such as Phormia nigricans, and adults, larvae and eggs of the flesh fly (Sarcophaga peregrina) of the Sarcophagidae family; Siphonaptera, for example, adults, larvae and eggs of the human flea (Pulex irritans) of the Pseudochilidae family; Blattoda, for example, the German cockroach (Blattella germanica) of the Blattidae family, and adults, larvae and eggs of the American cockroach (Periplaneta americana), the Smoky cockroach (Periplaneta fuliginosa), the Japanese cockroach (Periplaneta japonica), and the like; Orthoptera, for example, the spotted cricket (Diestrammena) of the Collegiidae family. Adults, larvae and eggs of the Japanese cockroach (Diestrammena apicalis) and the like; Phthiraptera, for example, head lice (Pediculus humanus humanus) of the family Pediculidae, and adults, larvae and eggs of the pubic louse (Phthirius pubis) of the family Pediculidae; Hemiptera, for example, bed bugs (Cimex lectularius) of the family Cimexidae, and adults, larvae and eggs of the assassin bug (Isyndus obscurus) of the family Triatominae;

[0099] The order Collembola of the class Insecta of the phylum Arthropoda, for example, adults, larvae and eggs of the purple springtail (Hypogastrura communis) of the family Hypogastrura; the order Acari of the class Arachnida, for example, Ixodes persulcatus of the family Ixodes, house dust mite (Ornithonyssus bacoti) of the family Ornithonyssida, Chelacaropsis moorei of the family Cheyletidae, louse mite (Pyemotes ventricosus) of the family Pyemotes, and Demodex of the family Demodex. Adults, larvae and eggs of the following spiders: Dermotophagoides pteronyssinus of the Pyridae family, Sarcoptes scabiei of the Sarcoptes family, Trombicula akamushi of the Tsutsugamushi family; Araneae, for example, Chiracanthium japonicum of the Clubriidae family, Heteropoda venatoria of the Huntsmanidae family, Spermophora japonica of the Pholcidae family, Adults, larvae and eggs of spiders from the order Scorpionidae, such as the spotted scorpion (Isometrus europaeus) of the family Scorpionidae;

[0100] Phylum Arthropoda, Class Chilopoda, Order Scolopendra, for example, adults, larvae and eggs of Scolopendra subspinipes mutilans and Scolopendra subspinipes japonica of the Scolopendra family; Order Scolopendra, for example, adults, larvae and eggs of Thereuronema hilgendofi of the Scolopendra family; Phylum Arthropoda, Class Diplopoda, Order Oxidus, for example, adults, larvae and eggs of Oxidus gracilis of the Oxiduidae family; Phylum Arthropoda, Class Crustacea, Order Isopoda, for example, Porcellio porcellio of the Porcellidae family adults, larvae and eggs of insects such as leeches (Haemadipsa zeylanica japonica) of the family Leechidae in the class Turphidae of the phylum Annelida; fungi such as Trichophyton rubrum and Trichophyton mentagrophytes which are ringworm fungi, Candida albicans which are candida fungi, and Aspergillus fumigatus which is an aspergillus fungus; gram-negative bacteria such as Escherichia coli and Pseudomonas aeruginosa; and gram-positive bacteria such as Staphylococcus aureus.

[0101] The compounds of the present invention represented by formula (1) are particularly valuable for controlling pests, such as arthropods, gastropods, nematodes, and fungi, that damage agricultural crops, trees, and ornamental plants in natural and artificial forests, as well as urban green spaces. In such situations, the compounds of the present invention can be present in their commercially useful formulations and in use forms prepared using these formulations, as mixtures with other active compounds, such as insecticides, acaricides, nematicides, fungicides, synergists, plant regulators, poison baits, or herbicides. Use forms include wettable powders, water-dispersible granules, dry flowables, water-soluble concentrates, emulsifiable concentrates, solutions, oil solutions, water-based suspensions, water-based emulsions, oil-based suspensions, capsules, dusts, granules, fine granules, baits, tablets, sprays, aerosols, and the like. To prepare these formulations, various pesticide adjuvants conventionally used in the agricultural and horticultural chemicals field can be used as appropriate. Such agricultural chemical adjuvants can be used for the purposes of, for example, improving the effectiveness, stabilization, and dispersibility of agricultural and horticultural chemicals.

[0102] Examples of agricultural chemical adjuvants include carriers (diluents), emulsifiers, wetting agents, dispersants, disintegrants, etc. Liquid carriers include water, aromatic hydrocarbons such as toluene and xylene, alcohols such as methanol, butanol, and glycol, ketones such as acetone, amides such as dimethylformamide, sulfoxides such as dimethyl sulfoxide, methylnaphthalene, cyclohexane, animal and vegetable oils, and fatty acids. Solid carriers include clay, kaolin, talc, diatomaceous earth, silica, calcium carbonate, montmorillonite, bentonite, feldspar, quartz, alumina, sawdust, nitrocellulose, starch, and gum arabic. Conventional surfactants can be used as emulsifiers and dispersants, including anionic surfactants such as higher alcohol sodium sulfate, stearyl trimethylammonium chloride, polyoxyethylene alkylphenyl ether, and lauryl betaine, cationic surfactants, nonionic surfactants, and amphoteric surfactants. Additionally, wetting agents such as dialkyl sulfosuccinate; adhesives such as carboxymethyl cellulose and polyvinyl alcohol; and disintegrants such as sodium lignosulfonate and sodium lauryl sulfate can be used. Of course, the compound of the present invention can be formulated as an active ingredient, either singly or in combination. 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. This content can be determined appropriately depending on various conditions, such as the formulation form and application method. For example, dusts can be formulated to contain about 0.5 to 20% by mass, preferably 1 to 10% by mass of the active ingredient; wettable powders can be formulated to contain about 1 to 90% by mass, preferably 10 to 80% by mass; and emulsifiable concentrates can be formulated to contain about 1 to 90% by mass, preferably 10 to 40% by mass of the active ingredient.

[0103] To control arthropods, gastropods, nematodes, and fungi, the compound is typically sprayed on the stems and leaves of plants in areas where damage by these pests has occurred or is likely to occur. Alternatively, the compound can be applied to the soil and absorbed by the roots, by incorporation into the entire soil layer, row application, incorporation into bed soil, treatment with cell seedlings, treatment in planting holes, treatment at the base of plants, top dressing, box treatment for rice, or application on the surface of water. It can also be used as a seed treatment such as seed immersion, seed dressing, or calper treatment, application to nutrient solutions in hydroponic (hydroponic) cultivation, or by fumigation or trunk injection. When used, the amount of active ingredient applied varies depending on the type and amount of pests, the type and cultivation form / growing condition of the target crop or tree, but generally 0.1 to 1000 g, preferably 1 to 100 g, of the active ingredient is applied per 10 ares. To treat these, wettable powders, water dispersible granules, dry flowable formulations, water-soluble concentrates, emulsifiable concentrates, liquid formulations, suspensions in water / emulsions in water, oily suspension formulations, capsules, etc. are diluted with water and sprayed 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 target plant, cultivation form, and growth conditions. Furthermore, dusts, sprays, or aerosol formulations can be applied to crops, etc. in their formulation form. 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 seedling bed, etc.; spraying granules at the base of the plant or a seedling bed, etc.; 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, row crops, etc. before sowing or planting the plants. For wettable powders, water dispersible granules, water-soluble concentrates, emulsifiable concentrates, liquid preparations, water suspensions / emulsions in water, oil suspension formulations, capsules, etc., they can be diluted with water and sprayed or irrigated into the soil at a rate of 5 to 500 liters per 10 ares, generally evenly over the entire area to be treated, while for dusts, granules, fine granules, baits, etc., they can be sprayed or irrigated in their formulations over the soil surface evenly over the entire area to be treated. Spraying or irrigation can also be done around seeds, crops, or trees that you want to protect from damage.Alternatively, the active ingredient can be mechanically dispersed by tilling during or after application.

[0104] For 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, or application at the time of transplanting. For example, formulations such as dust, water dispersible granules, granules, fine granules, emulsifiable concentrates, and suspensions in water may be used. Application can also be by mixing with the soil, such as mixing the soil with a dust, water dispersible granules, granules, or fine granules, for example, by mixing with the bed soil, covering the soil, or by mixing with the entire soil. Alternatively, the soil and various formulations may simply be layered alternately and applied. For application to paddy fields, solid formulations such as jumbo formulations, pack formulations, granules, and water dispersible granules, or liquid formulations such as emulsifiable concentrates and suspensions in water are typically sprayed on flooded paddy fields. Additionally, at the time of rice planting, appropriate formulations can be sprayed or injected directly or mixed with fertilizer or the like into the soil. Furthermore, by using a chemical solution such as an emulsion or aqueous suspension at the source of water flow into a paddy field, such as a water inlet or irrigation system, it can be applied in a labor-saving manner along with the water supply. Seed treatment methods include, for example, a method in which seeds are soaked in a liquid or solid formulation, diluted or undiluted, to allow the chemical to adhere to and penetrate the seeds, a method in which a solid or liquid formulation is mixed with the seeds and dusted to adhere to the seed surface, a method in which the formulation is mixed with an adhesive carrier such as a resin or polymer and then coated on the seeds, and a method in which the formulation is sprayed around the seeds at the same time as planting. The "seeds" to be treated in this way refer to plant bodies in the early stages 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 used for cutting cultivation. Furthermore, when applied, the term "soil" or "cultivation carrier" for plants refers to a support for cultivating crops, particularly a support for root growth. The material is not particularly limited as long as it is a material on which plants can grow, and may be so-called soil, seedling raising mat, water, etc. Specific examples of such materials include sand, pumice, vermiculite, diatomaceous earth, agar, gel-like substances, polymeric substances, rock wool, glass wool, wood chips, bark, etc. Treatments during the sowing and seedling raising stages of cultivated plants to be transplanted include direct treatment of seeds, as well as drenching of a liquid agent or spraying of granules on a seedling raising bed. It is also preferable to apply granules to the planting hole at the time of planting, or to mix them into the cultivation carrier near the transplanting site.

[0105] The compounds of the present invention represented by formula (1) are 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 cases, they can be controlled by spraying, injecting, irrigating, or applying oil solutions, emulsions, wettable powders, or aqueous suspensions to the wood or the surrounding soil, or by spraying dusts, granules, or the like. The oil solutions, emulsions, wettable powders, dusts, and the like used in this case can also be present as mixtures with other active compounds, such as insecticides, miticides, nematicides, fungicides, repellents, or synergists. These formulations may contain a total of 0.0001 to 95% by mass of the active ingredient compound, 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 aqueous suspensions. When controlling arthropods or fungi, etc., a 1m 2 0.01 to 100 g of the active ingredient compound is applied to the soil or wood surface.

[0106] The compound of the present invention represented by 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 stored as is, in powdered form, or mixed into products. It can also protect animal products (skin, hair, wool, feathers, etc.) and plant products (cotton, paper, etc.) from attack by lepidoptera, coleoptera, dust mites, and cockroaches when stored in their natural or converted forms, and it can also protect foods such as meat and fish from attack by lepidoptera, coleoptera, flies, and mites when stored. In such cases, pest control can be achieved by spraying oil solutions, emulsions, wettable powders, powders, etc.; applying resin vaporizers, etc.; treating with fumigants or aerosols; applying granules, tablets, or poison bait; or spraying aerosols. These formulations may also be present as mixtures with other active compounds, such as insecticides, acaricides, nematicides, fungicides, repellents or synergists, and these formulations may contain the active ingredient compounds in a total amount of 0.0001 to 95% by mass.

[0107] The compounds of the present invention represented by formula (1) are useful for the control or prevention of arthropods that parasitize the body surface of humans and livestock and cause direct harm by feeding on the skin or sucking blood, fungi, arthropods, nematodes, trematodes, cestodes, protozoa, and other arthropods that cause discomfort to humans, and can be incorporated into food or feed in small amounts, or can be administered orally in suitable orally ingestible pharmaceutical compositions, such as tablets, pills, capsules, pastes, gels, beverages, medicated feeds, medicated drinking water, medicated follow-up feeds, sustained-release large pills, and other sustained-release devices retained in the gastrointestinal tract, containing a pharmaceutically acceptable carrier or coating material, or transdermally in the form of sprays, powders, greases, creams, ointments, emulsions, lotions, spot-ons, pour-ons, shampoos, and the like. 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 topical administration, a device (e.g., a collar, medallion, ear tag, etc.) attached to the animal for local or systemic arthropod control can also be used.

[0108] Specific oral and transdermal administration methods for the compound of the present invention represented by formula (1) when used as an anthelmintic for animals such as livestock and pets, or for humans, are shown below, but the present invention is not necessarily limited to these methods. When orally administered as medicated drinking water, the drink is usually a solution, suspension, or dispersion in a suitable non-toxic solvent or water, together with a suspending agent such as bentonite, a wetting agent, or other excipients. The drink generally also contains an antifoaming agent. Drink formulations generally contain 0.01 to 1.0% by weight, preferably 0.01 to 0.1% by weight, of the active ingredient compound. When oral administration in a dry, solid, unit-use form is desired, capsules, pills, or tablets containing a predetermined amount of the active ingredient are usually used. These dosage forms are prepared by appropriately finely pulverizing the active ingredient and homogeneously mixing it with a diluent, filler, disintegrant, and / or binder, such as starch, lactose, talc, magnesium stearate, or vegetable gum. Such unit use formulations may vary widely in weight 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 body weight of the host.

[0109] When administered via animal feed, it can be homogenously dispersed in the feed, used as a top dressing, or used in pellet form. To achieve the desired antiparasitic effect, the final feed typically contains 0.0001 to 0.05% by weight, preferably 0.0005 to 0.01% by weight, of the active compound. The active compound, dissolved or dispersed in a liquid carrier vehicle, can be administered parenterally to animals via forestomach, 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. It can also be administered topically by mixing with a suitable carrier such as dimethyl sulfoxide or a hydrocarbon solvent. This formulation is applied directly to the external surface of the animal by spraying or direct pouring. The compound of the present invention represented by the formula (1) can also be used as an anthelmintic for arthropods that directly harm or are disease vectors, etc., in the surrounding environment where such pests may be present, by methods such as spraying, injecting, irrigating, or applying oil solutions, emulsions, wettable powders, etc., spraying powders, etc., treating with fumigants, heated aerosols such as mosquito coils, self-combustion type fumigants, and chemical reaction type aerosols, fumigants such as fogging, ULV agents, etc., placing granules, tablets, and poison bait, or adding floating powders, granules, etc. dropwise to waterways, wells, reservoirs, water tanks, and other running or stagnant water. Furthermore, agricultural and forest pests such as tussock moths can be controlled in the same manner as described above, or for flies, etc., a method in which the compound is mixed in livestock feed so that it mixes with the feces, and for mosquitoes, etc., a method in which the compound is vaporized into the air using an electric mosquito repellent, etc., are also effective. These formulations, which are the use forms, can also be present as mixtures with other active compounds, such as pest control agents, acaricides, nematode control agents, disease control agents, repellents, or synergists, and these formulations contain the active ingredient compounds in a total amount of 0.0001 to 95% by mass.

[0110] The compound of the present invention represented by the formula (1) can also be used as a mixture in combination with other active compounds. In particular, by using it in combination with a compound (insecticide) having insecticidal activity, acaricidal activity, or nematode activity, it is possible to expand the range of pests to be controlled in the control of pests such as arthropods, gastropods, and nematodes that damage plants, and synergistic effects such as reduced dosage can be expected. Specific examples of such active compounds include the following:

[0111] Organophosphates, such as acephate, azinphos-methyl, chlorpyrifos, diazinon, dichlorvos, dimeton-S-methyl, dimethoate, dimethylvinphos, vinphos), disulfoton, ethion, fenitrothion, fenthion, isoxathion, malathion, methamidophos, methidathion, monocrotophos Crotophos, naled, oxydeprofos, parathion, phenthoate, phosalone, pirimiphos-methyl, pyridaphenthion, profenofos, prothion prothiofos, propaphos, pyraclofos, salithione, sulprofos, thiometon, tetrachlorvinphos, trichlorphon, vamidothion and the like;Carbamate agents such as alanycarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, furathiocarb, isoprocarb, methomyl, metolcarb, pirimicarb, propoxur, thiodicarb, and the like; Organochlorine agents, such as aldrin, chlordane, DDT (p,p'-DDT), endosulfan, lindane, etc.;

[0112] Pyrethroids, such as acrinathrin, allethrin, bifenthrin, cycloprothrin, cyfluthrin, cyhalothrin, cyphenothrin, cypermethrin, deltamethrin, etofenprox, fenpropathrin, fenvalerate, and flucythrinate. , flufenprox, fluvalinate, furamethrin, halofenprox, imiprothrin, permethrin, phenothrin, prallethrin, pyrethrins, resmethrin, silafluofen, tefluthrin, tralomethrin, transfluthrin, and the like; Neonicotinoid agents, for example, acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, and the like;

[0113] Diamide agents, for example, chlorantraniliprole, cyantraniliprole, cyclaniliprole, flubenziamide, tetraniliprole, etc.; phenylpyrazole agents, for example, ethiprole, fipronil, acetoprole, pyrafluoprole, pyriprole, etc.; Nereistoxins, for example, bensultap, cartap, thiocyclam, thiosultap, etc.; insect growth regulators such as phenylbenzoylureas and diacylhydrazines, for example, chlorfluazuron, diflubenzuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflube, etc. zuron, triflumuron, buprofezin, chromafenozide, halofenozide, methoxyfenozide, tebufenozide, cyromazine, etc.; juvenile hormone agents, for example, diofenolan, fenoxycarb, hydroprene, methoprene, pyriproxyfen, etc.;

[0114] 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, such as anabasine, azadiractin, and deguelin. , fatty acid glyceride (decanolyoctanoylglycerol), hydroxypropyl starch, soybean lecithin, nicotine, nornicotine, sodium oleate, machine oil (petroleum oil), propylene glycol mono fatty acid ester, rapeseed oil, rotenone, sorbitan fatty acid ester, starch, etc.;Other insecticides include, for example, afidpyropene, benzpyrimoxan, broflanilide, chlorfenapyr, diafenthiuron, dichloromezotiaz, dimpropylidaz, DBEDC (Dodecylbenzenesulphonic acidbisethylenediamine copper [II]), salt), flonicamid, flometoquin, flufenerim, flupyradifurone, flupirimine, fluralaner, fluhexafon, fluxamethamide, hydramethylnon, indoxacarb, isocycloceram, metaflumizone, metaldehyde, nicotine sulfate sulfate, oxazosulfyl, pymetrozine, pyridalyl, pyrifluquinazone, spirotetramat, sulfoxaflor, tolfenpyrad, triazamate, triflumezopyrim, cyclopyrazoflor and the like;

[0115] Acaricides such as acequinocyl, acynonapyr, amidoflumet, amitraz, azocyclotin, benzomate, bifenazate, binapacryl, phenisobromorate, chinomethionate, nat), clofentezine, cyenopyrafen, cyflumetofen, tricyclohexyltin hydroxide (cyhexatin), dicofol, dienochlor, etoxazole, fenazaflor, fenazaquin, fenbutatin oxide (fenbutatin oxide), fenothiocarb, fenpyroximate, fluacrypyrim, hexythiazox, pyrimidifen, polynactins, propargyl, piflubumid ( pyflubamide, pyridaben, spirodiclofen, spiropidione, 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, isothiocyanate, morantel tartrate, oxamyl, thioxazafen, etc.; poison baits such as chlorophacinone, coumatetralyl, diphacinone, sodium fluoroacetate, warfarin, etc.

[0116] The compound of the present invention represented by formula (1) can also be used as a mixture with other active compounds other than compounds having insecticidal, acaricidal, or nematode-controlling activity. By using the compound in combination with a compound having fungicidal, herbicidal, or plant growth-regulating activity to control diseases and / or weeds that occur simultaneously during the application period, synergistic effects such as reduced control labor and reduced dosage can be expected. Furthermore, by using the compound in combination with a repellent, synergist, or the like, more effective control effects such as synergistic effects can be expected.

[0117] Specific examples of the active compound include disease control agents, such as DD (1,3-dichloropropene), acibenzolar-S-methyl, aldimorph, ametoctradin, amisulbrom, andoprim, triazine, azaconazole, azoxystrobin, and basic copper sulfate. sulfate), benodanil, benomyl, benthiavalicarb-isopropyl, benthiazole, bitertanol, bixafen, blasticidin S, boscalid, bromuconazole, calcium carbonate, buthiobate, lime sulfur mixture polysulfide), captafol, captan, carbendazole, carboxin, carpropamid, chinomethionate, chlorphenazole, chloroneb, chloropicrin, chlorothalonil, chlorzolinate, DBEDC (complex of bis(ethylenediamine)copper-bis-(dodecylbenzenesulfonic acid)),

[0118] Copper hydroxide, copper nonylphenol sulfonate, basic copper chloride oxychloride), cyazofamid, cyflufenamid, cymoxanil, cyproconazole, cyprodinil, dazomet, diclobutrazol, dichlofluanid, dichlorone, diclocymet, diclomezine, diethofencarb, difenoconazole, diflumetrim torim), dimethomorph, dimoxystrobin, diniconazole, diniconazole-M, dithane-stainless, dithianon, dodine, eclomezole, edifenphos, enestrobin, epoxiconazole, etaconazole, ethaboxam, shiitake mushroom mycelium extract from mushroom), famoxadone, fenamidone, fenarimol, fenbuconazole, fenfuran, fenhexamid,

[0119] Fenoxanil, fenpiclonil, fenpropidin, fenpyrazamine, ferimzone, fluazinam, flumetover, flumorph, fluopicolide picolide), fluopyram, fluorimide, fluotrimazole, fluoxastrobin, fluquinconazole, flusulfamide, flutolanil, fluquinconazole, Sapiroxad (fluxapyroxad), folpet (folpet), fosetyl aluminum (fosetyl-AL), fthalide (fthalide), fuberidazole (fuberidazole), fludioxonil (fludioxonil), fludirazole (flusilazole), flutianil (flutrianil), flutriafol (flutr iafol), furametpyr, fluconazole, guazatine, hexaconazole, hydroxyisoxazole, hymexazol, imazalil, imazalil sulfate, imibenconazole, iminoctadine acetate, iminoctadine-DBS, ipconazole,

[0120] 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, organosulfur nickel salts (nickel dimethyldithiocarbamate), nuarimol, orysastrobin, oxadixyl, oxathiapiprolin, organocupro (oxine-copper), oxolinic acid, oxpoconazole fumarate fumarate), oxycarboxin, oxytetracycline, pebulate, pefurazoate, penconazole, pencycuron, penflufen, penthiopyrad, picarbutrazox, picoxystrobin,

[0121] Piperalin, polycarbamate, polyoxin-B, polyoxin complexes, potassium hydrogen carbonate, probenazole, prochloraz, procymidone, propamocarb, propiconazole, propineb, proquinazid, prothioconazole, pyraclostrobin ), pyrametostrobin (pyrametostrobin), pyraoxystrobin (pyraoxystrobin), pyrazophos (pyrazophos), pyribencarb (pyribencarb), pyridinitrile (pyridinitrile), pyrifenox (pyrifenox), pyrimethanil (pyrimethanil), pyriophenone (pyriofenone), pyroquilon (pyroquilon), quinoxyfen (quinoxyfen), quintozene (quintozene), sedaxane (sedaxane), silver (silver), simeconazole (simeconazole), sodium hydrogen carbonate (sodium hydrogen carbonate), sodium hypochlorite (sodium hypochlorite), spiroxamine, streptomycin, sulfur, tebufloquine, tebuconazole, tecloftalam, terbinafine, tetraconazole, thiabendazole, thiadiazine, thifluzamide, thiophanate, thiophanate-methyl, thiuram, tiadinil,Tolclofos-methyl, tolclocarb, tolfluanid, triadimefon, triadimenol, triclopyrcarb, tricyclazole, tridemorph, trif Examples of such antivirals include roxystrobin, triflumizole, triforine, triticonazole, uniconazole-P, validamycin (-A), vinclozolin, zarilamide, zinc sulfate, zineb, ziram, and zoxamide.

[0122] Examples of compounds having herbicidal activity include aclonifen, acifluofen n-sodium, alachlor, alloxydim, and 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, dimethametrin yn), dinoterb, diquat, diuron, esprocarb, ethiozin, ethofumesate, ethoxysulfuron, etobenzanide, fenoxaprop-P-ethyl, fentrazamide, flucarbazone, flufenacet,Flurtamone, fluthiacet-methyl, foramsulfuron, glufosinate, glyphosate isopropylamine salt, glyphosate trimesium salt, imazapyr, imazosulfuron, indanofan,

[0123] Iodosulfuron, ioxynil-octanoate, isoproturon, isoxadifen, isoxaflutole, lactofen, linuron , mefenacet (mefenacet), mesosulfuron (mesosulfuron), metamitron (metamitron), methabenzthiazuron (methabenzthiazuron), metosulam (metosulam), metribuzin (metribuzin), napropamide (napropamide), neburon (neburon), oxadiargyl (oxadiazon), oxaziclomefone (o xaziclomefone, paraquat, pendimethalin, pentoxazone, phenmedipham, pretilachlor, propoxycarbazone, prosulfocarb, pyraclonil, pyraflufen-ethyl n-ethyl), pyrazolate, pyrazosulfuron-ethyl, pyributicarb, pyriftalid, pyriminobac-methyl, quizalofop-ethyl, sethoxydim, simazine, sulcotrione, sulfentrazone, thenylchlor, triaziflam, tribufos, and the like can be exemplified.

[0124] In addition, examples of compounds having a plant growth regulating effect include 1-naphthylacetamide (1-naphthylacetic acid), 4-CPA (4-CPA), benzylaminopurine (6-benzylaminopurine), butralin, calcium chloride, calcium formate, calcium peroxide, calcium sulfate, chlormequat chloride, choline, cyanamide, cyclanilide, daminozide, and decyl alcohol. alcohol), dichlorprop, ethephon, ethychlozate, flurprimidol, forchlorfenuron, gibberellin, indolebutyric acid, maleic hydrazide potassium salt, mefenpyr, mepiquat chloride, oxine sulfate, 8-hydroxyquinone It can also be used in combination with benzoyl perfluorooctyl ether, ...Repellents such as capsaicin, carane-3,4-diol, citronellal, deet, dimethyl phthalate, hinokitiol, limonene, linalool, menthol, menthone, naphthalene, thiuram, and the like; synergists such as methylenedioxynaphthalene, naphthyl propynyl ester, and the like; Examples of suitable amines include methyl methyl ether, nitrobenzyl thiocyanate, octachlorodipropyl ether, pentynyl phthalimide, phenyl salioxon, piperonyl butoxide, safrole, sesamex, sesamin, sulfoxide, triphenyl phosphate, and verbutin.

[0125] The compound of the present invention can be used as a biological pesticide in, for example, viral preparations such as cytoplasmic polyhedrosis virus (CPV), entomopox virus (EPV), granulosis virus (GV), and nuclear polyhedrosis virus (NPV), as well as in insecticides against Beauveria bassiana, Beauveria brongniartii, Monosporium phymatophagum, Paecilomyces fumosoroseus, and the like. Microbial pesticides used as insecticides or nematocides, such as Agrobacterium radiobacter, Bacillus subtilis, Agrobacterium radiobacter, Bacillus subtilis, Bacillus fumosoroseus, Pasteuria penetrans, Steinernema carpocapsae, Steinernema glaseri, Steinernema kushidai, Verticillium lecanii, etc., and subtilis, non-pathogenic Erwinia carotovora, non-pathogenic Fusarium oxysporum, Pseudomonas CAB-02, Pseudomonas fluorescens, Talaromyces flavus, Trichoderma atroviride, Trichoderma lignorum, and the like; Similar effects can be expected by mixing and using it with biological pesticides used as herbicides such as Pseudomonas campestris.

[0126] Furthermore, examples of biological pesticides include Amblyseius californicus, Amblyseius cucumeris, Amblyseius degenerans, Aphidius colemani, Aphidoletes aphidimyza, Chrysoperia carnea, Dacnusa sibirica, Diglyphus isaea, Encarsia japonica, and the like. formosa), desert glossy wasp (Eretmocerus eremicus), thrips (Franklinothrips vespiformis), two-spotted ladybird beetle (Harmonia axyridis), crown wasp (Hemiptarsenus varicornis), leafminer green wasp (Neochrysocharis formosa), two-spotted flower bug (Orius sauteri), strigicollis, and persimmon mite (Phytoseiulus It is also possible to use it in combination with natural enemies such as the Japanese stink bug (Pilophorus persimilis), the black gourd mist bug (Pilophorus typicus), and the giant stink bug (Piocoris varius), and pheromone agents such as codlerure, cuelure, geraniol, gyptol, librure, looplure, methyl eugenol, orfralure, peachfluor, phycilure, pyrimalure, and turpentine.

[0127] The present invention will be further explained in detail below by describing examples, formulation examples and test examples, but the scope of the present invention is not limited by these examples, formulation examples and test examples.

[0128] Example 1 Synthesis of N'-(1-(3-fluorophenyl)-2-methyl-3-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)propylidene)formhydrazide (compound number: A-121) represented by the following formula

[0129] 1-1: Synthesis of 1-(3-fluorophenyl)-3-hydroxy-2-methylpropan-1-one (compound number D-8) represented by the following formula

[0130] 3'-Fluoropropiophenone (3.1 g) was diluted with DMF (30 mL), 37% aqueous formaldehyde solution (1.94 g) was added, potassium carbonate (0.3 g) was added at room temperature, and the mixture was stirred and then allowed to stand overnight. Water and ethyl acetate were added to the reaction mixture, and the mixture was separated. The organic layer was washed with water and brine and dried over magnesium sulfate. The ethyl acetate was then distilled off under reduced pressure to obtain a crude product, which was purified by column chromatography to obtain 2.2 g of 1-(3-fluorophenyl)-3-hydroxy-2-methylpropan-1-one (oil) as compound (D-8).

[0131] 1-2: Synthesis of 3-chloro-1-(3-fluorophenyl)-2-methylpropan-1-one (compound number: E-8) represented by the following formula

[0132] 1-(3-fluorophenyl)-3-hydroxy-2-methylpropan-1-one (D-8) (2.1 g) was diluted with toluene (20 mL), thionyl chloride (1.6 g) and DMF (2 drops) were added, and the mixture was stirred at 60°C for 2 hours, after which excess thionyl chloride and toluene were distilled off from the reaction mixture. Ethyl acetate and an aqueous sodium hydrogencarbonate solution were added to the residue, the mixture was separated, washed with brine, and dried over magnesium sulfate. The ethyl acetate was then distilled off under reduced pressure to obtain 2.3 g (oil) of 3-chloro-1-(3-fluorophenyl)-2-methylpropan-1-one as compound (E-8).

[0133] 1-3: Synthesis of 1-(3-fluorophenyl)-2-methyl-3-(3-trifluoromethyl)-1H-1,2,4-triazol-1-yl)propan-1-one (compound number: C-10) represented by the following formula:

[0134]

[0135] 3-Chloro-1-(3-fluorophenyl)-2-methylpropan-1-one (E-8) (2.2 g) was diluted with DMF (20 ml), 3-(trifluoromethyl)1,2,4-triazole (1.7 g) was added, and potassium carbonate (1.80 g, 13 mmol) was added under ice-cooling. The mixture was stirred at room temperature for 6 hours and then allowed to stand overnight. After completion of the reaction, ethyl acetate and water were added to the reaction solution, and the layers were separated. The organic layer was washed with water and brine, dried over magnesium sulfate, and then the ethyl acetate was distilled off under reduced pressure. The resulting crude product was purified by column chromatography to obtain 2.0 g (oil) of 1-(3-fluorophenyl)-2-methyl-3-(3-trifluoromethyl)-1H-1,2,4-triazol-1-yl)propan-1-one as compound (C-10).

[0136] 1-4: Synthesis of N'-(1-(3-fluorophenyl)-2-methyl-3-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)propylidene)formhydrazide (compound number: A-121) represented by the following formula

[0137] 1-(3-Fluorophenyl)-2-methyl-3-(3-trifluoromethyl)-1H-1,2,4-triazol-1-yl)propan-1-one (C-10) (1.0 g) and acetic acid (91 μL) were dissolved in ethanol (10 mL), and hydrazine monohydrate (617 μL) was added thereto. After heating under reflux for 7 hours, water was added, and the mixture was extracted with ethyl acetate and washed with saturated brine. After drying over sodium sulfate and concentration, 924 mg of 1-(3-(3-fluorophenyl)-3-hydrazinylidene-2-methylpropyl)-3-(trifluoromethyl)-1H-1,2,4-triazole (B-10) was obtained as a residue. 724 mg of this compound without purification was dissolved in ethyl formate (10 mL), and formic acid (33 μL) was added thereto. After stirring overnight at room temperature, water was added, and the mixture was extracted with ethyl acetate and washed with saturated brine. After drying over sodium sulfate and concentration, the residue was purified by silica gel chromatography to obtain 341 mg (oil) of N'-(1-(3-fluorophenyl)-2-methyl-3-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)propylidene)formhydrazide as Compound A-121.

[0138] Example 2 Synthesis of N'-(1-(3-fluorophenyl)-2-methyl-3-(3-trifluoromethyl)-1H-1,2,4-triazol-1-yl)propylidene)-N,N-dimethylformhydrazonamide (compound number: A-125) represented by the following formula

[0139] 1-(3-(3-fluorophenyl)-3-hydrazinylidene-2-methylpropyl)-3-(trifluoromethyl)-1H-1,2,4-triazole (B-10) (187 mg) was dissolved in toluene (5 mL), N,N-dimethylformamide dimethyl acetal (228 μL) was added, and the reaction solution was heated under reflux for 3.5 hours. The organic solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 80 mg (oil) of N'-(1-(3-fluorophenyl)-2-methyl-3-(3-trifluoromethyl)-1H-1,2,4-triazol-1-yl)propylidene)-N,N-dimethylformhydrazonamide as compound A-125.

[0140] Example 3 Synthesis of N'-(1-(4-chlorophenyl)-2,2-dimethyl-3-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)propylidene)formhydrazide (compound number: A-295) represented by the following formula

[0141]

[0142] 3-1: Synthesis of 1-(4-chlorophenyl)-3-hydroxy-2,2-dimethylpropan-1-one (compound number: D-19) represented by the following formula

[0143]

[0144] 4'-Chloroisobutyrophenone (3.2 g) was dissolved in trifluoroacetic acid (15 mL), and paraformaldehyde (1.1 g) was added thereto, followed by heating under reflux for 14 hours. Subsequently, saturated aqueous sodium bicarbonate solution (20 mL), 48% aqueous sodium hydroxide solution (4.5 mL), and ethanol (5 mL) were added under ice-cooling. After stirring at room temperature for 6 hours, the mixture was extracted with ethyl acetate and washed with saturated brine. After drying over sodium sulfate, the mixture was concentrated, and the residue was purified by silica gel chromatography to obtain 3.3 g (oil) of 1-(4-chlorophenyl)-3-hydroxy-2,2-dimethylpropan-1-one as compound D-19.

[0145] 3-2: Synthesis of 3-(4-chlorophenyl)-2,2-dimethyl-3-oxopropyl 4-methylbenzenesulfonate (compound number: E-15) represented by the following formula

[0146]

[0147] 1-(4-chlorophenyl)-3-hydroxy-2,2-dimethylpropan-1-one (D-19) (3.3 g) was dissolved in pyridine (15 mL), and tosyl chloride (5.9 g) was added thereto under ice-cooling, followed by stirring at 60°C for 5.5 hours. 1N hydrochloric acid was then added, and the mixture was extracted with ethyl acetate and washed with saturated brine. After drying over sodium sulfate and concentration, 4.2 g (solid) of 3-(4-chlorophenyl)-2,2-dimethyl-3-oxopropyl 4-methylbenzenesulfonate was obtained as compound E-15.

[0148] 3-3: Synthesis of 1-(4-chlorophenyl)-2,2-dimethyl-3-(3-trifluoromethyl)-1H-1,2,4-triazol-1-yl)propan-1-one (compound number: C-26) represented by the following formula

[0149] 3-(4-chlorophenyl)-2,2-dimethyl-3-oxopropyl 4-methylbenzenesulfonate (E-15) (2.1 g), 3-(trifluoromethyl)-1,2,4-triazole (1.6 g), potassium carbonate (1.2 g), and N,N-dimethylformamide (15 mL) were placed in a microwave synthesis reaction vessel, and the mixture was irradiated with microwaves and reacted at 120°C for 2 hours. Water was then added, and the mixture was extracted with ethyl acetate and washed with saturated brine. After drying over sodium sulfate, the mixture was concentrated. The residue was purified by silica gel chromatography to obtain 1.8 g of 1-(4-chlorophenyl)-2,2-dimethyl-3-(3-trifluoromethyl)-1H-1,2,4-triazol-1-yl)propan-1-one (oil) as compound (C-26).

[0150] 3-4: Synthesis of N'-(1-(4-chlorophenyl)-2,2-dimethyl-3-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)propylidene)formhydrazide (compound number: A-295) represented by the following formula

[0151]

[0152] 1-(4-chlorophenyl)-2,2-dimethyl-3-(3-trifluoromethyl)-1H-1,2,4-triazol-1-yl)propan-1-one (C-26) (1.3 g) and acetic acid (118 μL) were dissolved in ethanol (15 mL), and hydrazine monohydrate (762 μL) was added thereto. After heating under reflux for 7 hours, water was added, and the mixture was extracted with ethyl acetate and washed with saturated brine. After drying over sodium sulfate and concentration, 1.5 g of 1-(3-(4-chlorophenyl)-3-hydrazinylidene-2,2-dimethylpropyl)-3-(trifluoromethyl)-1H-1,2,4-triazole (B-26) was obtained as a residue. 1.2 g of this compound without purification was dissolved in ethyl formate (10 mL), and formic acid (53 μL) was added thereto. After stirring overnight at room temperature, water was added, and the mixture was extracted with ethyl acetate and washed with saturated brine. After drying over sodium sulfate and concentration, the residue was purified by silica gel chromatography to obtain 662 mg (m.p. 120-121° C.) of N′-(1-(4-chlorophenyl)-2,2-dimethyl-3-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)propylidene)formhydrazide as Compound A-295.

[0153] Example 4 Synthesis of N'-(1-(4-fluorophenyl)-2,2-dimethyl-3-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)propylidene)-N-(2-propynyl)formhydrazide (compound number: A-298) represented by the following formula:

[0154] N'-(1-(4-chlorophenyl)-2,2-dimethyl-3-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)propylidene)formhydrazide (compound number: A-295) (100 mg) was dissolved in N,N-dimethylformamide (2 mL), potassium carbonate (50 mg) was added, the mixture was stirred, propargyl bromide (44 μL) was added at room temperature, and the mixture was stirred overnight at room temperature. Ethyl acetate and water were added to the reaction solution, and the organic layer was separated, and then further washed with water. The organic layer was dried over MgSO, and then the organic solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 111 mg (oil) of N'-(1-(4-fluorophenyl)-2,2-dimethyl-3-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)propylidene)-N-(2-propynyl)formhydrazide as compound A-298.

[0155] Example 5 Synthesis of N'-(1-(4-chlorophenyl)-2,2-dimethyl-3-(3-trifluoromethyl)-1H-1,2,4-triazol-1-yl)propylidene)-N,N-dimethylformhydrazonamide (compound number: A-299) represented by the following formula

[0156] 1-(3-(4-chlorophenyl)-3-hydrazinylidene-2,2-dimethylpropyl)-3-(trifluoromethyl)-1H-1,2,4-triazole (B-26) (245 mg) was dissolved in toluene (5 mL), N,N-dimethylformamide dimethyl acetal (237 μL) was added, and the reaction solution was heated under reflux for 3.5 hours. The organic solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 134 mg (oil) of N'-(1-(4-chlorophenyl)-2,2-dimethyl-3-(3-trifluoromethyl)-1H-1,2,4-triazol-1-yl)propylidene)-N,N-dimethylformhydrazonamide as compound A-299.

[0157] Example 6 Synthesis of methyl-N-(1-phenyl-2-methyl-3-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)propylidene)formhydrazonate (compound number: A-524) represented by the following formula

[0158] 1-(3-phenyl-3-hydrazinylidene-2-methylpropyl)-3-(trifluoromethyl)-1H-1,2,4-triazole (B-1) (526 mg) was dissolved in toluene (5 mL), trimethyl orthoformate (386 μL) was added, and the reaction solution was heated under reflux for 3 hours. The organic solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 290 mg (oil) of methyl-N-(1-phenyl-2-methyl-3-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)propylidene)formhydrazonate as compound A-524.

[0159] Regarding the synthesized compounds, including the compounds produced in the same manner as in the above examples, 1 The H-NMR data are shown in Tables 6 to 9 below. In Tables 6 to 9 below, the compound numbers are those listed in Tables 1 to 5, respectively.

[0160]

[0161]

[0162]

[0163]

[0164] Formulations containing the compounds of the present invention will be specifically described below using formulation examples, but the scope of the present invention is not limited in any way by the preparation methods of these formulations. In the formulation examples, all parts represent parts by mass.

[0165] Formulation Example 1 Emulsion A compound of the present invention (10 parts), xylene (60 parts), N-methyl-2-pyrrolidone (20 parts), and Sorpol 3005X (a mixture of a nonionic surfactant and an anionic surfactant, trade name of Toho Chemical Industry Co., Ltd.) (10 parts) were uniformly mixed and dissolved to obtain an emulsion.

[0166] Formulation Example 2 Wettable Powder The compound of the present invention (20 parts), Tokusil 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 then pulverized using a pulverizer to obtain a wettable powder.

[0167] 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 hydrogencarbonate (reagent) (92 parts) were uniformly mixed and then pulverized using a pulverizer to obtain a water-soluble compound.

[0168] Preparation Example 4 Water Dispersible Granules The compound of the present invention (20 parts), Demol N (naphthalenesulfonate formalin condensate, Kao Corporation, trade name) (5 parts), Air Roll CT-1L (dioctyl sulfosuccinate, Toho Chemical Industry Co., Ltd., trade name) (1 part), Cellogen 701A (carboxymethylcellulose, Daiichi Kogyo Seiyaku Co., Ltd.) (1 part) and kaolin clay (kaolinite, Takehara Chemical Industry Co., Ltd., trade name) (73 parts) were uniformly mixed and pulverized in an air mill. Water was added to this mixture and thoroughly kneaded, and then the mixture was extruded to granulate, dried and sized to obtain a water dispersible granule.

[0169] Formulation Example 5 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 substance, which was then thoroughly mixed with the pulverized slurry to obtain a flowable.

[0170] Formulation Example 6 EW-1 The compound of the present invention (20 parts) and Newcalgen D-230 (polyoxyethylene castor oil, Takemoto Oil & Fat Co., Ltd.) (15 parts) were mixed and homogenized, and then water (59.8 parts) was gradually added with stirring to obtain a dispersion. This dispersion was then added to KELZAN (xanthan gum, Sansho Co., Ltd.) (0.2 parts) dispersed in propylene glycol (reagent) (5.0 parts), to obtain an emulsion formulation.

[0171] Formulation Example 7 EW-2 The compound of the present invention (10 parts) was dissolved in xylene (10 parts) and mixed with Rheodol 430V (polyoxyethylene sorbit tetraoleate, Kao Corporation) (24 parts) to obtain a dispersion. This dispersion and water (50.8 parts) were dispersed using a homogenizer, and KELZAN (xanthan gum, Sansho Co., Ltd.) (0.2 parts) dispersed in propylene glycol (reagent) (5.0 parts) was added to obtain an emulsion formulation.

[0172] Formulation Example 8 Microemulsion A 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) were uniformly mixed to obtain a microemulsion.

[0173] Formulation Example 9 Liquid Preparation A compound of the present invention (20 parts), N-methyl-2-pyrrolidone (reagent) (70 parts), and Newcalgen D-230 (polyoxyethylene castor oil, Takemoto Oil & Fat Co., Ltd.) (10 parts) were uniformly mixed and dissolved to obtain a liquid preparation.

[0174] Formulation Example 10 Granule-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 Industries Co., Ltd.) (30 parts), and NK-300 (clay, Showa KDE Co., Ltd.) (63 parts) were uniformly mixed, and water was added and the mixture was thoroughly kneaded. The mixture was then extruded to granulate, and dried and sized to obtain granules.

[0175] Formulation Example 11 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.

[0176] Formulation Example 12 Fine Granules-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.

[0177] Formulation Example 13: Microgranules-2 The compound of the present invention (5 parts) and Toxil GU-N (5 parts) were mixed, pulverized using a micropulverizer, and then uniformly mixed with Iide silica sand (silica sand, JFE Mineral Co., Ltd.) (80 parts). This mixture was further mixed while spraying with a diluted aqueous solution of Toxanon GR-31A (polycarboxylic acid surfactant, Sanyo Chemical Industries, Ltd.) (10 parts), to obtain a granular composition. This granular composition was dried to obtain microgranules.

[0178] Formulation Example 14: Dust A compound of the present invention (5 parts), Tokusil 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 dust.

[0179] Formulation Example 15 DL Dust A 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.

[0180] Formulation Example 16: 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 dust. Pre-moistened seeds and this dust were mixed and air-dried to obtain coated seeds.

[0181] Formulation Example 17 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-pulverized in 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. The pulverized slurry and the prepared gel were thoroughly mixed to obtain a flowable. This flowable was mixed with seeds and air-dried to obtain coated seeds.

[0182] Formulation Example 18 Oil suspension formulation A compound of the present invention (20 parts), Newkalgen C-120 (POE tristyrylphenyl ether, Takemoto Yushi Co., Ltd., trade name) (5 parts), Rheodol TW-O120V (POE sorbitan monooleate, Kao Corporation, trade name) (10 parts), methyl oleate (Kanto Chemical Co., Inc., reagent) (62 parts), and Esben NZ (organic bentonite, Hojun Co., Ltd., trade name) (3 parts) were thoroughly mixed and dispersed, and the resulting slurry dispersion was wet-pulverized to obtain an oil suspension formulation.

[0183] The effects and usefulness of the compounds of the present invention will now be described with reference to specific examples. The compounds used for comparison are indicated by the following compound symbols.

[0184] Comparative agent A (No. 6 described in JP-A-8-073436)

[0185] 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 (400 ppm) of an emulsion prepared according to Formulation Example 1 was irrigated therein, followed by sowing tomatoes (13 seeds / pot). After sowing, the plants were grown in a greenhouse. 17 days after sowing, the degree of root galling for each plant was evaluated on a 5-point scale based on the following evaluation criteria, and the root-knot index and control value were calculated based on the following formula.

[0186] Root gall severity (evaluation criteria): 0 (no root galls), 1 (1-2 root galls), 2 (3 or more root galls), 3 (large or connected root galls present. Less than 50% of the roots present), 4 (root galls present on 50% or more of the roots) Root gall index = Σ (root gall severity x number of plants concerned) / (4 x number of plants surveyed) Control value (%) = [1 - (root gall index of treated area / root gall index of untreated area)] x 100

[0187] As a result, compound numbers (A-1, A-5, A-17, A-21, A-22, A-27, A-28, A-30, A-33, A-42, A-47, A-51, A-52, A-71, A-75, A-83, A-87, A-91, A-95, A-121, A-125, A-131, A-132, A-133, A-134, A-135, A-136, A-137, A-138, A-139, A-140, A-141, A-142, A-143) were obtained. , A-144, A-146, A-147, A-148, A-149, A-151, A-161, A-171, A-176, A-177, A-178, A-179, A-181, A-182, A-184, A-185 , A-186, A-194, A-195, A-196, A-197, A-234, A-237, A-238, A-244, A-254, A-264, A-269, A-270, A-271, A-272, A-274, A-277, A-287, A-288, A-295, A-296, A-297, A-298, A-300, A-303, A-307, A-308, A-341, A-342, A-343, A-344, A-345, A-346, A-349, A-351, A-371, A-372, A-373, A-374, A-375, A-376, A-377, A-378, A-379, A-381, A-382, A-383, A-384, A The compounds of the present invention (A-386, A-389, A-391, A-393, A-394, A-396, A-411, A-412, A-414, A-421, A-431, A-441, A-442, A-502, A-507, A-508, A-509, A-510, A-511, A-515, A-516, A-517, A-519, A-523, A-524, A-525, A-526, A-527, C-37) showed control values ​​of 70% or more. On the other hand, the control rate of Comparative Agent A was 0%.

[0188] Test Example 2: Density suppression test against tomato rust mite (Aculops lycopersici Massee) A 430 ml polyethylene cup containing water was covered with a lid having a hole (approximately 5 mm in diameter) in the center. A slit approximately 5 mm wide was made in a circular filter paper with a diameter of 6.5 cm, and the downward-hanging strip-shaped portion 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 top of the filter paper. In this way, three leaf disks (1 cm x 1 cm) made from tomato leaflets in the early stage of true leaf development were placed underside up on the absorbent cotton, with the cup constantly replenished with water, and small pieces of tomato rust mite-infested leaves were inoculated onto the disks. 24 hours after inoculation, the small pieces were removed, and the cups were placed in an acrylic cylinder 50 cm high and 10 cm in diameter. 2.0 ml of a water-diluted emulsion (500 ppm) prepared according to Formulation Example 1 was sprayed per cup using an airbrush. After spraying, the plants were kept in a constant temperature room at 25°C. Seven days after treatment, the next generation density suppression rate 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 conducted using one cup per group.

[0189] 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

[0190] As a result, compound numbers (A-1, A-5, A-17, A-21, A-22, A-26, A-27, A-30, A-33, A-42, A-46, A-47, A-51, A-52, A-56, A-75, A-95, A-121, A-125, A-131, A-132, A-133, A-134, A-135, A-136, A-137, A-138, A-139, A-140, A-141, A-142, A-143, A-144, A-145, A-146, A-147, A-148, A-149, A-200, A-201, A-202, A-203, A-204, A-205, A-206, A-207, A-208, A-210, A-211, A-212, A-213, A-214, A-215, A-216, A-217, A-218, A-219, A-220, A-221, A-222, A-223, A-224, A-225, A-226, A-227, A-228, A-229, A-230, A-231, A-232, A-233, A-234, A-235, A-236, A-237, A-238, A-239, A-240, A-241, A-242, A-243, A-244, A-245, A-246, A-247, A-248, A-249, A -147, A-148, A-149, A-161, A-171, A-176, A-177, A-178, A-179, A-181, A-182, A-184, A-185, A-186, A-187, A-197, A-234, A-237, A-238, A-254, A-264, A-269, A-270, A-271, A-272, A-274, A-275, A-276, A-277, A-285, A-286, A-287, A-288, A-289, A-295, A-296, A-297, A-298, A-299, A-300, A-301, A-302, A-303, A-304, A-305, A-307, A-308, A-309, A-341, A-342, A-343 , A-344, A-346, A-347, A-348, A-349, A-351, A-350, A-371, A-372, A-373, A-374, A-375, A-376, A-377, A-378, A-379, A-381 , A-382, A-383, A-384, A-385, A-387, A-388, A-389, A-391, A-392, A-393, A-394, A-396, A-398, A-399, A-411, A-412, A-414, A-421, A-431, A-502, A-503, A-504, A-505, A-509, A-515, A-516, A-517, A-525, A-526, A-527) showed a control rate of 90% or more. On the other hand, the control rate of Comparative Agent A was 0%.

Claims

1. Below formula (1), or a salt thereof. 1-6 Alkyl group, C 2-6 Alkenyl group, C 2-6 R represents an alkynyl group or a benzyl group; R represents a formyl group; or R and R together represent the following formula: R5 may form a group represented by the formula: 1-6 R represents a hydrogen atom or a C 1-6 R represents an alkyl group; 1-6 R7 and R8 may be bonded to each other and together with the nitrogen atom to which R7 and R8 are bonded form a saturated 4- to 7-membered ring; R3 is C 1-6 R represents a hydrogen atom or a C 1-6 R3 and R4 together may form a (C3-C6)-carbocyclic ring, X is a hydrogen atom, C 1-6 Alkyl group, C 1-6 Haloalkyl group, C 1-6 Alkoxy group, C 1-6 represents a haloalkoxy group, a halogen atom, a cyano group, or a nitro group, and when there are a plurality of X's, they may be the same or different from each other; n represents an integer of 1 to 5; Y1, Y2, Y3, and Y4 each independently represent a nitrogen atom or a CR group; R represents a hydrogen atom, a halogen atom, C 1-6 Alkyl group or C 1-6 It is a haloalkyl group, and when there are a plurality of R, they may be the same or different.

2. Y2 represents CR, R represents C 1-6 The hydrazone derivative or salt thereof according to claim 1 , which represents a haloalkyl group.

3. A hydrazone derivative represented by the following formula (2): [In the formula, R is a hydrogen atom, C 1-6 Alkyl group, C 2-6 Alkenyl group, C 2-6 R3 represents an alkynyl group or a benzyl group; 1-6 R represents a hydrogen atom or a C 1-6 R3 and R4 together may form a (C3-C6)-carbocyclic ring, X is a hydrogen atom, C 1-6 Alkyl group, C 1-6 Haloalkyl group, C 1-6 Alkoxy group, C 1-6 represents a haloalkoxy group, a halogen atom, a cyano group, or a nitro group, and when there are a plurality of X's, they may be the same or different from each other; n represents an integer of 1 to 5; Y1, Y2, Y3, and Y4 each independently represent a nitrogen atom or a CR group; R represents a hydrogen atom, a halogen atom, C 1-6 Alkyl group or C 1-6 It represents a haloalkyl group, and when there are a plurality of R's, they may be the same or different.

4. A ketone derivative represented by the following formula (3). [Wherein R3 is C 1-6 R represents a hydrogen atom or a C 1-6 R3 and R4 together may form a (C3-C6)-carbocyclic ring, X is a hydrogen atom, C 1-6 Alkyl group, C 1-6 Haloalkyl group, C 1-6 Alkoxy group, C 1-6 represents a haloalkoxy group, a halogen atom, a cyano group, or a nitro group, and when there are a plurality of X's, they may be the same or different from each other; n represents an integer of 1 to 5; Y1, Y2, Y3, and Y4 each independently represent a nitrogen atom or a CR group; R represents a hydrogen atom, a halogen atom, C 1-6 Alkyl group or C 1-6 It represents a haloalkyl group, and when there are a plurality of R's, they may be the same or different.

5. Below formula (4), [In the formula, R is a hydrogen atom, C 1-6 Alkyl group, C 2-6 Alkenyl group, C 2-6 R3 represents an alkynyl group or a benzyl group; 1-6 R represents a hydrogen atom or a C 1-6 R3 and R4 together may form a (C3-C6)-carbocyclic ring, X is a hydrogen atom, C 1-6 Alkyl group, C 1-6 Haloalkyl group, C 1-6 Alkoxy group, C 1-6 represents a haloalkoxy group, a halogen atom, a cyano group, or a nitro group, and when there are a plurality of X's, they may be the same or different from each other; n represents an integer of 1 to 5; Y1, Y2, Y3, and Y4 each independently represent a nitrogen atom or a CR group; R represents a hydrogen atom, a halogen atom, C 1-6 Alkyl group or C 1-6 A method for producing a hydrazone derivative represented by the following formula (2): [wherein R1, R3, R4, X, Y1, Y2, Y3, Y4 and n are as defined in the above formula (4)] are reacted with formic acid and / or a hydrazone derivative represented by the following formula (5): HCOOR9 (5) [wherein R9 is C 1-6 The present invention relates to a method for producing a compound having the formula (I), which comprises reacting a compound having the formula (I) with a formic acid ester represented by the formula (I):

6. Below formula (6), [In the formula, R5 represents OR6 or NR7R8, R6 represents C 1-6 R represents a hydrogen atom or a C 1-6 R represents an alkyl group; 1-6 R7 and R8 may be bonded to each other and together with the nitrogen atom to which R7 and R8 are bonded form a saturated 4- to 7-membered ring; R3 is C 1-6 R represents a hydrogen atom or a C 1-6 R3 and R4 together may form a (C3-C6)-carbocyclic ring, X is a hydrogen atom, C 1-6 Alkyl group, C 1-6 Haloalkyl group, C 1-6 Alkoxy group, C 1-6 represents a haloalkoxy group, a halogen atom, a cyano group, or a nitro group, and when there are a plurality of X's, they may be the same or different from each other; n represents an integer of 1 to 5; Y1, Y2, Y3, and Y4 each independently represent a nitrogen atom or a CR group; R represents a hydrogen atom, a halogen atom, C 1-6 Alkyl group or C 1-6 A method for producing a hydrazone derivative represented by the following formula (7): [wherein R, R, X, Y, Y, Y, Y, and n are as defined in the above formula (6)], [In the formula, R5 is as defined in the above formula (6), and R9 is C 1-6 and n is an integer of 1 to 5. The present invention relates to a method for producing a carboxylic acid derivative having a structure comprising reacting a carboxylic acid derivative having a structure represented by the formula:

7. Below formula (9), [In the formula, R7 is a hydrogen atom or C 1-6 R represents an alkyl group; 1-6 R7 and R8 may be bonded to each other and together with the nitrogen atom to which R7 and R8 are bonded form a saturated 4- to 7-membered ring; R3 is C 1-6 R represents a hydrogen atom or a C 1-6 R3 and R4 together may form a (C3-C6)-carbocyclic ring, X is a hydrogen atom, C 1-6 Alkyl group, C 1-6 Haloalkyl group, C 1-6 Alkoxy group, C 1-6 represents a haloalkoxy group, a halogen atom, a cyano group, or a nitro group, and when there are a plurality of X's, they may be the same or different from each other; n represents an integer of 1 to 5; Y1, Y2, Y3, and Y4 each independently represent a nitrogen atom or a CR group; R represents a hydrogen atom, a halogen atom, C 1-6 Alkyl group or C 1-6 A method for producing a hydrazone derivative represented by the following formula (10): [In the formula, R, R, X, Y, Y, Y, Y, and n are as defined in the above formula (9), and R is C 1-6 represents an alkyl group.] is reacted with a hydrazone derivative represented by the following formula (11): [wherein R7 and R8 are as defined in formula (9) above] with an amine derivative represented by the following formula:

8. Below formula (4), [In the formula, R is a hydrogen atom, C 1-6 Alkyl group, C 2-6 Alkenyl group, C 2-6 R3 represents an alkynyl group or a benzyl group; 1-6 R represents a hydrogen atom or a C 1-6 R3 and R4 together may form a (C3-C6)-carbocyclic ring, X is a hydrogen atom, C 1-6 Alkyl group, C 1-6 Haloalkyl group, C 1-6 Alkoxy group, C 1-6 represents a haloalkoxy group, a halogen atom, a cyano group, or a nitro group, and when there are a plurality of X's, they may be the same or different from each other; n represents an integer of 1 to 5; Y1, Y2, Y3, and Y4 each independently represent a nitrogen atom or a CR group; R represents a hydrogen atom, a halogen atom, C 1-6 Alkyl group or C 1-6 A method for producing a hydrazone derivative represented by the following formula (12): [wherein R, R, X, Y, Y, Y, Y, and n are as defined in formula (4)], [wherein R1 is as defined in formula (4) above, and Z represents a chlorine atom, a bromine atom, an iodine atom, a methanesulfonyloxy group, a p-toluenesulfonyloxy group, or a trifluoromethanesulfonyloxy group.] 9. Below formula (2), [In the formula, R is a hydrogen atom, C 1-6 Alkyl group, C 2-6 Alkenyl group, C 2-6 R3 represents an alkynyl group or a benzyl group; 1-6 R represents a hydrogen atom or a C 1-6 R3 and R4 together may form a (C3-C6)-carbocyclic ring, X is a hydrogen atom, C 1-6 Alkyl group, C 1-6 Haloalkyl group, C 1-6 Alkoxy group, C 1-6 represents a haloalkoxy group, a halogen atom, a cyano group, or a nitro group, and when there are a plurality of X's, they may be the same or different from each other; n represents an integer of 1 to 5; Y1, Y2, Y3, and Y4 each independently represent a nitrogen atom or a CR group; R represents a hydrogen atom, a halogen atom, C 1-6 Alkyl group or C 1-6 wherein R represents a haloalkyl group, and when there are a plurality of R's, they may be the same or different from each other. [wherein R, R, X, Y, Y, Y, Y, and n are as defined in formula (2)], [wherein R1 is as defined in formula (2)] with a hydrazine derivative represented by the following formula:

10. An agricultural or horticultural agent containing the hydrazone derivative or its salt according to claim 1 or 2.

11. An agricultural and horticultural nematode control agent containing the hydrazone derivative or its salt according to claim 1 or 2.

12. An agricultural and horticultural pest control agent containing the hydrazone derivative or its salt according to claim 1 or 2.

13. A method for controlling plant pests, comprising treating the pests and / or their habitat and / or seeds and / or plant propagation material with an agricultural or horticultural agent as defined in claim 10.

14. A method for preventing plant pests, comprising a step of treating an area where a useful crop is to be grown or is being grown, or the growing crop, with the agricultural and horticultural agent according to claim 10.

15. A method for preparing an agricultural chemical composition, comprising the step of mixing the hydrazone derivative or its salt according to claim 1 or 2 with any one of a carrier, an emulsifier, a wetting agent, a dispersant and a disintegrant, or a combination of any of these.

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