Novel hydrazone derivatives and agricultural / horticultural insecticides containing them as active ingredients

Abstract

This invention provides a compound that exhibits excellent efficacy as an agricultural and horticultural pesticide, particularly as an insecticide against aphids and other pests. [Solution] As an active ingredient, a hydrazone derivative represented by the following formula (1) or (2) or a salt thereof is provided. In the formula, X1 represents a hydrogen atom or a halogen atom, and R1 is C 1-6 It represents an alkyl group, and R2 is C 1-6 The compound represents an alkoxy group or a dialkylamino group, where X2 is a hydrogen atom and R5 is a hydrogen atom, or where X2 is a chlorine atom and R5 represents an ethoxy group. JPEG2026144560000030.jpg2789

Description

[Technical Field]

[0001] The present invention relates to novel hydrazone derivatives or salts thereof, and agricultural and horticultural chemicals containing these compounds as active ingredients, particularly agricultural and horticultural pest control agents for aphids, and methods for using the same. [Background technology]

[0002] In the agricultural and horticultural fields, plant pest and disease control agents have been developed and put into practical use to control various diseases and pests. However, the emergence of pests or diseases that have acquired resistance to these agents is a problem, and there is a strong need for the development of superior agents against such pests or diseases. Patent Document 1 discloses compounds that include compounds represented by the following formula (IX) and have aphidicidal activity.

[0003] [ka] However, the compounds described in Patent Document 1 are limited to compounds having an N-formylhydrazone structure, and compounds having substituents represented by the following formula (A) are not disclosed. Furthermore, compounds in which the carbon atoms of the hydrazone structure have an ethyl group along with a phenyl group are not specifically disclosed.

[0004] [ka]

[0005] Patent Document 2 discloses compounds that have insecticidal activity and include compounds represented by the following formula 4.

[0006] [ka] However, Patent Document 2 does not disclose any compounds having substituents represented by the above formula (A), nor does it specifically disclose any compounds in which the carbon atoms of the hydrazone structure have ethyl groups along with phenyl groups. Furthermore, there is no description regarding aphid-killing effects.

[0007] Patent documents 3 and 4 do not disclose any compounds having the structure shown by formula (A) above, nor do they disclose any compounds defined by specific substituent combinations of formula (2) below.

[0008] [ka] [In the formula, X2 represents a hydrogen atom and R5 represents a hydrogen atom, or X2 represents a chlorine atom and R5 represents an ethoxy group.] Furthermore, while Patent Documents 3 and 4 disclose compounds having nematodic activity, they do not mention aphidicidal effects.

[0009] Patent Document 5 describes compounds useful as anthelmintics, but does not disclose any compounds having the structure shown in formula (A) above, and is limited to hydrazone compounds having a pyridine ring, and furthermore, does not mention insecticides for agricultural and horticultural use.

[0010] Patent document 6 describes hydrazone compounds as reaction intermediates for agricultural fungicides, but does not disclose any compounds having the structure shown in formula (A) above, nor does it disclose the biological activity of these intermediates. [Prior art documents] [Patent Documents]

[0011] [Patent Document 1] U.S. Patent No. 3708591 [Patent Document 2] U.S. Patent No. 3549767 [Patent Document 3] Japanese Unexamined Patent Publication No. Sho 63-93761 [Patent Document 4] EP 0254461 Specification [Patent Document 5] Japanese Unexamined Patent Publication No. Sho 62-501709 [Patent Document 6] EP 0172031 Specification [Summary of the Invention] [Problems to be Solved by the Invention]

[0012] In crop production in agriculture and horticulture, damage caused by harmful insects and diseases is still serious at present, and the development of excellent agricultural and horticultural chemicals against pests and diseases resistant to existing agents is desired. [Means for Solving the Problems]

[0013] The inventors of the present invention have conducted intensive studies to solve the above problems, and as a result, have found that a hydrazone derivative having a specific structure is useful as an agricultural and horticultural chemical, particularly as an agricultural and horticultural pest control agent against aphids and the like, and have completed the present invention. Furthermore, it has been found that a hydrazone derivative having a combination of specific substituents exhibits an extremely excellent aphicidal effect, and thus the present invention has been completed.

[0014] That is, the present invention provides: 1. The following formula (1), [Chemical Formula] [in the formula, R1 is C 1-6 represents an alkyl group, R2 is C 1-6 represents an alkoxy group or NR3R4, R3 is C 1-6 represents an alkyl group, R4 is C 1-6 represents an alkyl group, X1 represents a hydrogen atom or a halogen atom.] a hydrazone derivative represented by or a salt thereof, 2. Agricultural and horticultural insecticide containing the hydrazone derivative or salt thereof described in item 1 above as an active ingredient, 3.Equation (2) below, [ka] [In the formula, X2 represents a hydrogen atom and R5 represents a hydrogen atom, or, X2 represents a chlorine atom, and R5 represents an ethoxy group. Hydrazone derivatives or salts thereof, 4. Agricultural and horticultural insecticides containing the hydrazone derivative or salt thereof described in item 3 above as an active ingredient. 5. The above-mentioned agricultural and horticultural insecticide is an insecticide for aphids, as described in item 4 above. This concerns... [Effects of the Invention]

[0015] The compounds of the present invention exhibit excellent efficacy as agricultural and horticultural pest control agents, particularly against aphids and other horticultural pests. [Modes for carrying out the invention]

[0016] The present invention relates to the following formula (1), [ka] [In the formula, R1 is C 1-6 It shows an alkyl group, R2 is C 1-6 It shows an alkoxy group or NR3R4, R3 is C 1-6 It shows an alkyl group, R4 is C 1-6 It shows an alkyl group, X1 represents a hydrogen atom or a halogen atom. A hydrazone derivative or salt thereof, as shown in, The following formula (2), [ka] [In the formula, X2 represents a hydrogen atom and R5 represents a hydrogen atom, or X2 represents a chlorine atom and R5 represents an ethoxy group.] relates to a hydrazone derivative represented by or a salt thereof.

[0017] In this specification, the "halogen atom" refers to a chlorine atom, a bromine atom, an iodine atom or a fluorine atom. "C 1-6 alkyl group" is a linear or branched alkyl group. Examples of such alkyl groups preferably include methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, s-butyl group, t-butyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, n-hexyl group, isohexyl group, etc. The number of carbon atoms in the alkyl group is 1 to 6, preferably 1 to 3.

[0018] "C 1-6 alkoxy group" is a linear or branched alkyl group bonded to an oxygen atom. Examples of such alkoxy groups preferably include methoxy group, ethoxy group, n-propoxy group, isopropoxy group, cyclopropyloxy group, n-butoxy group, sec-butoxy group, tert-butoxy group, n-pentoxy group, n-hexyloxy group, etc. The number of carbon atoms in the alkoxy group is 1 to 6, preferably 1 to 4.

[0019] Examples of the salt of the hydrazone derivative represented by the formula (1) of the present invention include inorganic acid salts such as hydrochloride, sulfate, nitrate, phosphate, etc., and organic acid salts such as acetate, fumarate, maleate, oxalate, methanesulfonate, benzenesulfonate, p-toluenesulfonate, etc. The compound of the present invention may contain one or more asymmetric centers in its structural formula, and two or more optical isomers and diastereomers may exist. The present invention includes all individual optical isomers and all mixtures containing them in any ratio. Furthermore, while the compounds of the present invention may have two or more geometric isomers derived from carbon-carbon double bonds or carbon-nitrogen double bonds in their structural formulas, the present invention encompasses all of these geometric isomers and mixtures containing them in any proportion. For example, in the compounds described herein, the dashed lines in the structural formula indicate that the compound encompasses any of the two or more geometric isomers derived from a carbon-carbon double bond or a carbon-nitrogen double bond.

[0020] In the hydrazone derivative represented by formula (1) of the present invention, it is preferable that R1 represents an ethyl group. In the hydrazone derivative represented by formula (1) of the present invention, R2 is C 1-2 An alkoxy group or NR3R4 is represented, where R3 is C 1-6 It represents an alkyl group, and R4 is C 1-6 It is preferable to represent an alkyl group.

[0021] The following describes typical methods for producing the hydrazone derivative represented by formula (1) or (2) of the present invention, but the methods for producing the above compounds are not limited in any way to these methods in the present invention.

[0022] Reaction Equation 1 [ka] [In the formula, R1 and X1 are as defined in formula (1) above.] In the method shown in reaction formula 1, the hydrazone derivative represented by formula (5) can be produced by reacting the ketone compound represented by formula (3) and the hydrazine represented by formula (4) in an inert solvent, either in the presence or absence of an acid. The compound represented by formula (3) is a generally known compound.

[0023] The inert solvent used in the reaction between the ketone compound represented by formula (3) and the hydrazine represented by formula (4) can be any known solvent, as long as it is inert to the reaction. Examples of such solvents include methanol, alcohols such as 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; and solvents such as N-methylpyrrolidone, N,N'-dimethylimidazolinone, and acetonitrile. These solvents can be used individually or mixed in combination of two or more as needed. Any known inorganic or organic acid can be used as the acid in the reaction between the compound represented by formula (3) and the hydrazine represented by formula (4). 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 individually or in combination of two or more.

[0024] The acid used in the reaction between the compound represented by formula (3) and the hydrazine represented by formula (4) can be used in an amount of 0.001 to 2 equivalents, preferably 0.01 to 1 equivalent, relative to the ketone compound represented by formula (3). The ratio of the ketone compound represented by formula (3) to the hydrazine represented by formula (4) can be appropriately selected from a wide range, but it is preferable to use 1 to 10 moles or more of the latter for every 1 mole of the former, and more preferably 2.0 to 5.0 moles. The reaction is preferably carried out at 0°C to the boiling point of the solvent used, and more preferably at room temperature under reflux. The reaction time varies depending on the reaction temperature and other factors, and cannot be stated definitively, but the reaction is usually completed in about 0.1 to 24 hours. After the reaction is complete, the target product can be isolated from the reaction system by conventional methods, and if necessary, the target product can be produced by purification using recrystallization or column chromatography. Alternatively, the target product can be used in the next reaction step without isolating it from the reaction system.

[0025] Reaction Equation 2 [ka] [In the formula, R6 is C 1-6 This represents an alkyl group, where R1, R2, and X1 are as defined in formula (1) above. Regarding reaction equation 2, specific embodiments include those shown in reaction equations 3, 4, and 5 described below.

[0026] Reaction Equation 3 [ka] [In the formula, R6 is C 1-6 This represents an alkyl group, where R1 and X1 are as defined in formula (1) above. In reaction formula 3, the hydrazone derivative represented by formula (8) can be produced by the reaction of the hydrazone derivative represented by formula (5) with orthoformate ester (7). The compounds represented by formulas (5) and (7) are generally known compounds.

[0027] The solvent used in the reaction between the hydrazone compound represented by formula (5) and the orthoformic acid ester represented by formula (7) can be a wide range of known solvents, 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; alcoholic solvents such as methanol and ethanol; esteric 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 individually or mixed in combination of two or more as needed.

[0028] Examples of orthoformate esters (7) used in the iminomination reaction of hydrazone compounds represented by formula (5) include methyl orthoformate, ethyl orthoformate, propyl orthoformate, and butyl orthoformate. Such orthoformate esters (7) can be used in amounts of 1 to 20 equivalents, preferably 2 to 10 equivalents, relative to the hydrazone derivative represented by formula (5). This reaction can usually be carried out within a range from -78°C to the boiling point of the solvent used, and it is preferable to carry out the reaction between 0°C and the boiling point. The reaction time varies depending on the reaction temperature and other factors, and cannot be stated definitively, but the reaction is usually completed in about 0.1 to 24 hours. The target compounds obtained from 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, or distillation.

[0029] Reaction Equation 4 [ka] [In the formula, R6 is C 1-6 Hereinafter, R1, R3, R4, and X1 represent alkyl groups, as defined in formula (1) above. In reaction formula 4, the hydrazone derivative represented by formula (10) can be produced by the reaction of the hydrazone derivative represented by formula (8) with the amine derivative represented by formula (9). The amine derivative represented by formula (9) is generally a known compound.

[0030] The solvent used in the amination reaction of the hydrazone compound represented by formula (8) above can be a wide range of known solvents, 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; alcoholic solvents such as methanol and ethanol; esteric 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 individually or mixed in combination of two or more as needed. The amine derivative (9) can be used in an amount of 1 to 5 equivalents, preferably 1 to 2.5 equivalents, relative to the hydrazone derivative represented by formula (8).

[0031] This reaction can usually be carried out within a range from -78°C to the boiling point of the solvent used, and it is preferable to carry out the reaction between 0°C and the boiling point. The reaction time varies depending on the reaction temperature and other factors, and cannot be stated definitively, but the reaction is usually completed in about 0.1 to 24 hours. The target compounds obtained from 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, or distillation.

[0032] Reaction Equation 5 [ka] [In the formula, R6 is C 1-6 Hereinafter, R1, R3, R4, and X1 represent alkyl groups, as defined in formula (1) above. In reaction formula 5, the hydrazone derivative represented by formula (10) can be produced by the reaction of the hydrazone derivative represented by formula (5) with the acetal derivative (11). The acetal derivative represented by formula (11) is generally a known compound.

[0033] The solvent used in the reaction between the hydrazone compound represented by formula (5) and the acetal derivative represented by formula (11) can be a wide range of known solvents, 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; alcoholic solvents such as methanol and ethanol; esteric 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 individually or mixed in combination of two or more as needed. Examples of acetal derivatives (11) used in the iminoization reaction of the hydrazone compound represented by formula (5) include N,N-dimethylformamide dimethylacetal. The acetal derivative (11) can be used in an amount of 1 to 10 equivalents, preferably 1 to 5 equivalents, relative to the hydrazone derivative represented by formula (5). This reaction can usually be carried out within a range from -78°C to the boiling point of the solvent used, and it is preferable to carry out the reaction between 0°C and the boiling point. The reaction time varies depending on the reaction temperature and other factors, and cannot be stated definitively, but the reaction is usually completed in about 0.1 to 24 hours. The target compounds obtained from 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, or distillation.

[0034] Reaction Equation 6 [ka] [In the formula, X2 and R5 are as defined in formula (2) above.]

[0035] In reaction formula 6, the hydrazone derivative represented by formula (2) can be produced by reacting the ketone compound represented by formula (12) and the hydrazine compound represented by formula (13) in an inert solvent, either in the presence or absence of an acid. The compounds represented by formulas (12) and (13) are generally known compounds.

[0036] The solvent used in the reaction between the ketone compound represented by formula (12) and the human radine compound of formula (13) can be a wide range of known solvents, 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; alcoholic solvents such as methanol and ethanol; esteric 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 individually or mixed in combination of two or more as needed.

[0037] Any known inorganic or organic acid can be used as the acid in the reaction between the compound of formula (12) and the compound of formula (13). 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 individually or in combination of two or more. The acid used in the reaction between the compound of formula (12) and the compound of formula (13) can be used in an amount of typically 0.001 to 2 equivalents, preferably 0.01 to 1 equivalent, relative to the ketone compound represented by formula (12). The ratio of the ketone compound of formula (12) to the hydrazine compound represented by formula (13) can be appropriately selected from a wide range, but it is preferable to use 1 to 10 moles or more of the latter for every 1 mole of the former, and more preferably 2.0 to 5.0 moles.

[0038] This reaction can usually be carried out within a range from -78°C to the boiling point of the solvent used, and is more preferably carried out at room temperature under reflux. The reaction time varies depending on the reaction temperature and other factors, and cannot be stated definitively, but the reaction is usually completed in about 0.1 to 24 hours. The target compounds obtained from 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, or distillation.

[0039] Table 1 below shows representative compounds of the hydrazone derivative represented by formula (1), and Table 2 below shows representative compounds of the hydrazone derivative represented by formula (2). However, the scope of the present invention is not limited to these compounds. In Tables 1 and 2, physical properties are indicated as characteristics or melting point (°C), where "Me" indicates a methyl group and "Et" indicates an ethyl group.

[0040] General formula (1)

[0041] [ka] [Table 1]

[0042] General formula (2) [ka] [Table 2]

[0043] The compounds of the present invention can be used to prevent or control organisms that cause harm to livestock or in various other situations, such as in agriculture, indoors, in forests, or for hygiene purposes. Specific usage scenarios, target pests, and methods of use are shown below, but the scope of the present invention is not limited in any way by these usage scenarios, target pests, or methods of use. The compound of the present invention represented by formula (1) above is used in agricultural crops, for example, food crops (grains such as rice, barley, wheat, rye, and oats, corn, potatoes, sweet potatoes, taro, soybeans, adzuki beans, broad beans, peas, green beans, peanuts, and other legumes), vegetables (cruciferous crops such as cabbage, Chinese cabbage, radish, turnip, broccoli, cauliflower, and komatsuna, pumpkin, cucumber) (Watermelon, cantaloupe, melon and other gourds, eggplant, tomato, bell pepper, pepper, okra, spinach, lettuce, lotus root, carrot, burdock, garlic, onion, leek and other alliums, etc.), mushrooms (shiitake, button 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 (including Mycobacteria, Myxomycetes, Bacteria, Actinomycetes, etc.), and bacteria that damage ornamental crops (lavender, rosemary, thyme, parsley, pepper, ginger, etc.), special crops (tobacco, tea, sugar beets, sugarcane, hops, cotton, hemp, olives, rubber, coffee, etc.), pasture and fodder crops (timothy, clover, alfalfa, corn, sorghum, orchardgrass, grasses, legumes, etc.), turfgrasses (Korean grass, bentgrass, etc.), forest trees (fir, spruce, pine, cypress, cedar, hinoki, etc.), and ornamental plants (herbaceous plants and flowers such as chrysanthemums, roses, carnations, orchids, and garden trees such as ginkgo, cherry, and Japanese laurel).

[0044] Specific examples of pests include the following: The order Lepidoptera of the class Insecta, phylum Arthropoda, for example, Noctuidae species such as Helicoverpa armigera, Heliothis spp., Agrotis segetum, Autographa nigrisigna, Trichoplusia ni, Mamestra brassicae, Spodoptera exigua, Spodoptera litura, etc., Pseudaletia separata, Tylenidae species such as Plutella xylostella, Tortricidae species such as Adoxophyes orana fasciata, Adoxophyes honmai, Archips (fuscocupreanus), tea leaf roller (Homona magnanima), tea leaf moth (Caloptilia theivora), pear leaf moth (Grapholita molesta), etc., Psychidae family (Eumeta minuscula), etc.

[0045] Leaf miners include species such as Lyonetia prunifoliella malinella and Lyonetia clerkella from the family Lyonetidae, Phyllocnistis citrella from the family Lyonetidae, Phyllonorycter ringoniella from the family Thysanthidae, Acrolepiopsis sapporensis from the family Tineidae, Synanthedin hector from the family Solanidae, Stathmopoda masinissa from the family Pectinophora gossypiella from the family Glaucidae, Carposina niponensis from the family Carposidae, and Cossus from the family Cossidae. Jezoensis, etc.; Nemapogon granella of the Tineidae family, etc.; Monema flavecens of the Limacodidae family, Parasa lepida, Scopelodes contracus, etc.; Ostrinia furnacalis, Chilo suppressalis, Scirpophaga incertulas, Cnaphalocrocis medinalis, Hellulla undalis, Conogethes punctiferlis, etc. of the Crambidae family.

[0046] This includes species such as Diaphania indica, Parapediasia teterrella, Locastra muscosalis (a type of Pyralidae), Parnasara guttata (a type of Hesperiidae), Papilio xuthus (a type of Papilionidae), Pieris rapae crucivora (a type of Pieridae), Lampides boeticus (a type of Lycaenidae), Ascotis selenaria (a type of Geometrid moth), Agrius convolvuli (a type of Sphingidae), Phalera flavescens (a type of Notodontidae), and Malacosoma neustrium (a type of Lasiocampidae). Adults, larvae, and eggs of species such as testaceum, Saturnia japonica (family Saturidae), Euproctis pseudoconspersa (family Lymantriidae), Orgyia thyellina (family Orgyia thyellina), and Telochurus recens approximans (family Lymantriidae), Spirosoma imparilis (family Arctiidae), Hyphantria cunea (family Arctiidae), grapeberry moss (Endopiza viteana), and codling moth (Laspeyresia pomonella);

[0047] Coleoptera, for example, the Scarabaeidae family (Anomala cuprea, Popillia japonica, Oxycetonia jucunda, Anomala geniculata, etc.), the Buprestidae family (Agrilus auriventris, etc.), the Elateridae family (Melanotus fortnumi, etc.), the Coccinellidae family (Epilachna vigintioctopunctata, etc.), the Cerambycidae family (Anoplophora malasiaca, Xylotrechus pyrrhoderus, etc.), the Chrysomelidae family (Aulacophora femoralis, Diabrotica, etc.) (spp.), *Phyllotreta striolata*, *Cassida nebulosa*, *Phaedon brassicae*, *Oulema oryzae*, *Epilachna varivestis*, *Leptinotarsa ​​decemlineata*, etc., *Rhynchites heros* of the Attelabidae family, *Cylas formicarius* of the Curculidae family, *Curculio sikkimensis*, *Lissorhoptrus oryzophilus*, *Anthonomus gradis grandis*, *Sphenophrus venatus* of the Curculidae family Adults, larvae, and eggs of species such as *Epuraea domina* (a type of sap beetle) of the Nitidulidae family;

[0048] Heteroptera of the order Hemiptera, such as the Pentatomidae family (Eurydema rugosum, Eysarcoris lewisi, Eysarcoris parvus, Nezara viridula, Plautia stali, Halymorpha mista, etc.), the Quercus family (Urochela luteovoria, etc.), the rice bug (Lagynotomus elongatus), the Lycaenidae family (Togo hemipterus, etc.), and the Coreidae family (Riptortus) Adults, larvae, and eggs of species such as clavatus, Cletus punctiger, Leptocorisa chinensis (family Reptiliidae), Dysdeercus cingulatus (family Dysdeeridae), Stephanitis nashi (family Stephanitis family), Stephanitis pyrioides (family Stephanidae), Apolygus spinolai, Stenotus rubrovittalus, Trigonotylus coelestialium (family Miridae), and Megacopta punctatissimum (family Bean Bug);

[0049] Homoptera of the order Hemiptera, such as Platypleura kaempferi of the family Cicadidae, Arboridia apicalis, Empoasca onukii, Nephotettix cincticeps, Nephotettix virescens of the family Cicadellidae, Laodelphax striatellus, Nilaparvata lugens, Sogatella furcifera of the family Planthoppers, Geisha distinctissima of the family Planthoppers, and Psyllidae Psyllidae Psyllidae This includes various biotypes of whiteflies such as the citrus whitefly (Diaphorina citri), the citrus whitefly (Aleurocanthus spiniferus), the silverleaf whitefly (Bemisia argentifolii), and the tobacco whitefly (Bemisia tabaci) from the family Diaphoridae, as well as the citrus whitefly (Dialeurodes citri) and the greenhouse whitefly (Trialeurodes vaporariorum), the grape aphid (Viteus vitifolii) from the family Phylloxera, and the spirea aphid (Aphis citricola), bean aphid (Aphis craccivora), cotton aphid (Aphis gossypii), potato aphid (Aulacorthum solani), and radish aphid (Brevicoryne). brassicae), citrus aphid (Toxoptera aurantii), citrus black aphid (Toxoptera citricidus), elderberry aphid (Aulacorthum magnoliae), pear aphid (Schizaphis piricola), pear green aphid (Nippolachnus piri), false radish aphid (Lipaphis erysimi), peach aphid (Hyalopterus)pruni), chrysanthemum aphid (Pleotrichophorus chrysanthemi), chrysanthemum long-horned aphid (Macrosiphoniella sanborni), broad bean long-horned aphid (Megoura crassicauda), thorny long-horned aphid (Sitobion ibarae),

[0050] Tulip aphid (Macrosiphum euphorbiae), corn aphid (Myzus varians), peach aphid (Myzus persicae), land aphid (Rhopalosiphum rufiabdominalis), wheat aphid (Rhopalosiphum padi), wheat aphid (Sitobion akebiae), apple mealybug (Eriosoma lanigerum), etc., Icerya purchasi of the family Coccidae, mulberry mealybug (Pseudococcus comstocki), citrus mealybug (Phenacoccus viburnae), wisteria mealybug (Phenacoccus Adults, larvae, and eggs of scale insects such as the horned scale insect (Ceroplastes ceriferus) and ruby ​​scale insect (Ceroplastes rubens) of the family Coccidae, and the red scale insect (Aonidiella aurantii), pear scale insect (Comstockaspis perniciosa), mulberry scale insect (Pseudaulacaspis pentagoa), and Yanon scale insect (Unaspis yanonensis) of the family Coccidae;

[0051] Adults, larvae, and eggs of the order Thysanoptera, such as the tea thrips (Scirtothrips dorsalis), southern thrips (Thrips palmi), onion thrips (Thrips tabaci), soybean thrips (Thrips setosus), flat-headed thrips (Frankliniella intonsa), citrus thrips (Frankliniella occidentalis), and croton thrips (Heliothrips haemorrhoidalis) of the family Thysanoptera, and adults of the family Ponticulothrips (Ponticulothrips diospyrosi) and rice thrips (Haplothrips aculeatus); Adults, larvae, and eggs of Hymenoptera, such as the turnip sawfly (Athalia rosae ruficornis) and rose sawfly (Arge pagana) of the Tenthredinidae family, the apple sawfly (Arge mali) of the Tenthredinidae family, the chestnut gall wasp (Dryocsmus kuriphilus) of the Gall wasp family, the rose leafcutter wasp (Megachile nipponica nipponica) of the Leafcutter bee family, and the black ant (Formica japonica), the large ant (Camponotus kiusiuensis), the black garden ant (Lasius fuliginosus), and the fire ant (Solenopsis richteri, S. invicta, S. geminata) of the Formicidae family;

[0052] Diptera, for example, the soybean pod gall midge (Asphondylia yushimai) of the family Gall Midgeidae, the cherry fruit fly (Rhacochlaena japonica) and the melon fly (Bactrocera cucurbitae) of the family Tephritidae, the rice shore fly (Hydrellia griseola) of the family Nephritidae, the cherry fruit fly (Drosophila suzukii) of the family Drosophilidae, the bean leafminer (Liriomyza trifolii), the tomato leafminer (Liriomyza sativae), the cabbage leafminer (Chromatomyia horticola), the rice leafminer (Agromyza oryzae), the eggplant leafminer (Liriomyza bryoniae) of the family Delia Adults, larvae, and eggs of onion flies (Delia antiqua), etc. Adults, larvae, and eggs of grasshoppers of the order Orthoptera, such as the migratory locust (Locusta migratoria) of the family Acrididae, the long-horned grasshopper (Ruspolia lineosa) of the family Tettigoniidae, the field cricket (Teleogryllus emma) and the green grasshopper (Truljalia hibinonis) of the family Gryllidae, the mole cricket (Gryllotalpa orientalis) of the family Gryllotalpa, and the short-winged grasshopper (Oxya yezoensis) of the family Acrididae; Adults, larvae, and eggs of termites (Isoptera), such as the Taiwanese termite (Odontotermes formosanus) of the family Termitidae; Adults, larvae, and eggs of the order Dermaptera, such as the earwig Labidura riparia of the family Dermaptidae;

[0053] Adults, larvae, and eggs of Collembola, order Collembola, such as Sminthurus viridis of the family Sminthurusidae and Onychiurus matsumotoi of the family Onychiurusidae; Adults, larvae, and eggs of Isopada, order Malacostraca, order Isopoda, such as Armadillidium vulgare of the family Armadillididae; The order Acari (Acari) of the class Arachnida (Arachnida), for example, Polyphagotarsonemus latus and Phytonemus pallidus of the family Miridae, Penthaleus major of the family Pterididae, Brevipalpus lewisi and Brevipalpus phoenicis of the family Pterididae, and Panonychus citri, Panonychus ulmi, Tetranychus urticae, Tetranychus kanzawai, Amphitetranychus viennensis, Oligonychus ununguis and Bryobia of the family Miridae. Adults, larvae, and eggs of mites such as *Eotetranychus kankitus*, *Bryobia praetiosa*, 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 (Colomerus vitis), peach rust mite (Aculus fockeui), tea rust mite (Calacarus carinatus), and other mites of the family Tyrophagus putrescentiae and robini;

[0054] This includes species of the order Architaenioglossa (primitive snails) of the class Gastropoda (mollusks), such as the apple snail (Pomacea canaliculata) of the family Pomacea, and species of the order Plumonata (primitive snails), such as the African giant snail (Achatina fulica) of the family Achatidae, the common slug (Meghimatium bilineatum) of the family Melalidae, the common garden slug (Milax gagates) of the family Melalidae, the brown garden slug (Lehmannina valentiana) of the family Melalidae, and the thin-skinned snail (Acusta despecta sieboldiana) of the family Melalidae; The order Tylenchida of the class Phantom Instrumenta in the phylum Nematoda, for example, the potato rot nematode (Ditylenchus destructor) of the family Anguillidae, the common nematode (Tylenchorhynchus claytoni) of the family Tylenkolinchidae, the northern root-knot nematode (Pratylenchus penetrans) and southern root-knot nematode (Pratylenchus coffeae) of the family Platylenchidae, the common nematode (Helicotylenchus dihystera) of the family Hoplorymidae, the potato cyst nematode (Globodera rostochiensis) of the family Heterodera, the sweet potato root-knot nematode (Meloidogyne incognita) of the family Meloidogyneidae, and the cat nematode (Criconema) of the family Chryconeidae. Examples include *Nothotylenchus acris* of the Anguillidae family and *Aphelecchoides fragarriae* of the Aphelencoides family; and *Drilimylae* of the Caudata class, such as *Xiphinema sp.* of the Longidoridae family and *Trichodorus sp.* of the Trichodoridae family. Fungi and bacteria such as Eumycota, Myxomycota, Bacteriomycota, and Actinomycota.

[0055] Diseases to which the compound of the present invention represented by formula (1) can be applied include, specifically, rice blast (Pyricularia oryzae), sesame leaf spot (Cochliobolus miyabeanus), sheath blight (Rhizoctonia solani), glume browning (Pantoea ananatis), brown stripe disease (Acidovorax avene subsp. avenae), leaf sheath browning (Pseudomonas fuscovaginae), bacterial leaf blight (Xanthomonas oryzae pv. oryzae), bacterial damping-off (Burkholderia plantarii), etc.; and wheat powdery mildew (Erysiphe graminis), Fusarium head blight (Gibberella zeae), red rust (Puccinia striiformis, P. graminis, P. recondita, P. hordei), and snow mold (Typhula sp., Micronectriella). Examples include: nivalis, smut (Ustilago tritici, U. nuda), smut (Tilletia caries), eye spot disease (Pseudocercosporella herpotrichoides), cloud spot disease (Rhynchosporium secalis), leaf blight (Septoria tritici), flammation (Leptosphaeria nodorum), net-like spot disease (Pyrenophora teres), leopard spot disease (Helminthosporium zonatum Ikata), black knot disease (Pseudomonas syringae pv. japonica), etc.; citrus black spot disease (Diaporthe citri), scab (Elsinoe fawcetti), fruit rot (Penicillium digitatum, P. italicum), brown rot (Phytophthora citrophthora, P. nicotianae), black spot disease (Phyllosticta (citricarpa), etc.; Monilinia mali (apple disease),

[0056] Diseases such as 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), cedar-apple rust (Gymnosporangium yamadae), gray mold (Monilinia fructicola), etc.; pear black spot (Venturia nashicola, V. pirina), black spot (Alternaria kikuchiana), cedar-apple rust (Gymnosporangium haraeanum), gray mold (Monilinia fructigena), etc.; peach gray mold (Monilinia fructicola), black spot (Cladosporium carpophilum), Phomopsis rot (Phomopsis) sp.) Bacterial hole disease (Brenneria nigrifluens), etc.; grape black rot (Elsinoe ampelina), late blight (Colletotrichum acutatum), powdery mildew (Uncinula necator), rust (Phakopsora ampelopsidis), black rot (Guignardia bidwellii), downy mildew (Plasmopara viticola), gray mold (Monilinia fructigena), black spot (Cladosporium viticolum), gray mold (Botrytis cinerea), bacterial crown gall (Agrobacterium vitis), etc.; persimmon anthracnose (Gloeosporium kaki), leaf spot (Cercospora kaki, Mycoshaerella nawae), etc.; cucurbit anthracnose (Colletotrichum lagenarium), powdery mildew (Sphaerotheca fuliginea, Oidiopsis taurica), vine blight (Didymella bryoniae), vine wilt (Fusarium oxysporum), downy mildew (Pseudoperonospora cubensis), late blight (Phytophthora sp.), seedling blight (Pythium sp.), etc.; cucumber bacterial spot (Pseudomonas syringae pv. lochrymans), bacterial edge blight (Pseudomonas viridiflava), bacterial brown spot (Xanthomonas campestris pv. cucurbitae), etc.; melon bacterial brown spot (Xanthomonas campestris pv. cucurbitae), root rot (Agrobacterium rhizogens), canker (Streptomyces sp.), etc.; watermelon bacterial fruit spot (Acidovorax avenae pv.(citrulli), etc.; bacterial wilt of solanaceous vegetables (Ralstonia solanacearum), etc.; tomato ring spot (Alternaria solani), leaf mold (Cladosporium fulvum), late blight (Phytophthora infestans), canker (Clavibacter michiganense subsp. michiganense), etc.

[0057] Stem necrosis (Pseudomonas corrugata), soft rot (Pectobacterium carotovorum subsp. carotovorum), etc.; eggplant brown spot (Phomopsis vexans), powdery mildew (Erysiphe cichoracearum), etc.; black spot (Alternaria japonica), white spot (Cercosporella brassicae), soft rot (Pectobacterium carotovorum subsp. carotovorum), etc. of cruciferous vegetables; cabbage rot (Pseudomonas syringae pv. marginalis), black rot (Xanthomonas campestris pv. campestris), etc.; lettuce rot (Pseudomonas cichorii, Pseudomonas viridiflava), bacterial leaf spot (Xanthomonas campestris pv. vitians), onion rust (Puccinia). allii), etc.; soybean purple spot disease (Cercospora kikuchii), black rot (Elsinoe glycines), black spot disease (Diaporthe phaseolorum var. sojae), etc.; kidney bean anthracnose (Colletotrichum lindemthianum), etc.; peanut black spot disease (Cercospora personata), brown spot disease (Cercospora arachidicola), etc.; pea powdery mildew (Erysiphe pisi), etc.; potato summer blight (Alternaria solani), late blight (Phytophthora infestans), leaf blight (Rhizoctonia solani), etc.; strawberry powdery mildew (Sphaerotheca humuli), etc.; tea net blight (Exobasidium reticulatum), white spot disease (Elsinoe Leucospila), red blight (Pseudomonas syringae pv. theae), canker (Xanthomonas campestris pv.(Theicola), etc.; tobacco diseases such as cedar-apple rust (Alternaria longipes), powdery mildew (Erysiphe cichoracearum), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacina), late blight (Phytophthora nicotianae), damping-off (Ralstonia solanacearum), and cavity disease (Pectobacterium carotovorum subsp. carotovorum); sugar beet diseases such as brown spot (Cercospora beticola) and seedling blight (Aphanomyces cochliodes);

[0058] 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), sclerotinia rot (Sclerotinia sclerotiorum) in various crops such as eggplant, cucumber, and lettuce; snow mold (Pythium iwayamai, Tyohula incarnate, Fusarium nivale, Sclerotinia borealis), powdery mildew (Erysiphe graminis), furling disease (Lycoperdon perlatum, Lepista subnudo, Marasmius oreades), pseudoleaf blight (Ceratobasidium) in grasses. Examples include spp., damping-off (Gaemannomyces graminis), Curvularia leaf blight (Curvularia geniculata), leaf rot (Rhizoctonia solani), Pythium blight (Pythium periplocum, Pythium vanterpoolii), rust (Puccinia spp.), dollar spot (Sclerotinia homoeocarpa), etc.; and red burn (Pythium aphanidermatum) and anthracnose (Colletotrichum sp.) of bentgrass.

[0059] The compound of the present invention represented by formula (1) can also be used to control arthropods and fungi that are active indoors in buildings, including ordinary houses, and that damage or rot wood and its processed products such as wooden furniture, stored food, clothing, books, etc., thereby harming our lives. Specific examples of harmful organisms include the following: Adults, larvae, and eggs of termites in the order Termitida, class Insecta, phylum Arthropoda, such as the Formosanus termite (Coptotermes formosanus), Reticulitermes speratus (Reticulitermes speratus), and other termites of the genus Reticulitermes (Reticulitermes hesperus, R. tibialis, R. flavipes, R. lucifugus, R. santonensis, etc.), the Incisitermes minor (Incisitermes minor), the Taiwanese termite (Odontotermes formosanus) of the family Termitidae, Hodotermopsis jzponica of the family Termitidae, and the domestic termite (Cryptotermes domesticus) of the family Termitidae; Coleoptera, for example, the rice weevil (Sitophilus zeamais) and soybean weevil (Sitophilus zeamais) of the Curculionidae family, the adzuki bean weevil (Callosobruchus chinensis), the pea weevil (Bruchus pisorum), the broad bean weevil (Bruchus rufimanus) of the Bean Weevilidae family, the confused flour beetle (Tribolium castaneum), the flat-headed confused flour beetle (Tribolium confusum) of the Tenebrionidae family, the sawtoothed flat beetle (Oryzaephilus surinamensis), the square-breasted flat beetle (Cryptolestes pusillus) of the Slender Flat Beetle family, and the cigarette beetle (Lasioderma serricorne), the drugstore beetle (Stegobium) of the Cigarette Beetle family Adults, larvae, and eggs of various species including the Dermestidae family (Attagenus unicolor japonicus, Anthrenus verbasci, Dermestes maculatus, etc.), the Dermesidae family (Gibbium aequinnoctiale, etc.), the Dinoderidae family (Dinoderus minutus, Rhizopertha dominica, etc.), and the Lyctus brunneus family (Lyctus brunneus, etc.);

[0060] Adults, larvae, and eggs of Lepidoptera, for example, Pyralidae species such as Cadra cautella, Ephestia kuehniella, and Plodia interpunctella; Glauciidae species such as Sitotroga cerealella; Tinea translucens and Tineola bisselliella; Tineidae species such as Tinea translucens and Tineola bisselliella; Adults, larvae, and eggs of Psocoptera, for example, Psocoptidae species such as Lepinotus reticulatus and Liposcelis bostrychophilus; Cockroaches, such as the German cockroach (Blattella germanica) of the family Blattidae, the American cockroach (Periplaneta fuliginosa), and the Japanese cockroach (Periplaneta japonica), including adults, larvae, and eggs; and wasps, such as the house ant (Monomorium pharaoni) and the small ant (Monomorium nipponense) of the family Formicidae, including adults, larvae, and eggs;

[0061] Silverfish, such as adults, larvae, and eggs of species in the family Silverfish (Ctenolepisma villosa, Lepisma saccharina, etc.); Adults, larvae, and eggs of flies of the order Diptera, such as Drosophila melangogaster of the family Drosophilidae and Piophila casei of the family Piophilidae; Adults, larvae, and eggs of mites in the order Acari of the class Arachnida, such as Tyrophagus putrescentiae and Lardoglyphus konoi of the family Tyrophagidae, and Carpoglyphus lactis of the family Carpoglyphidae; Wood-decaying fungi such as Tyromyces palustris and Coriolus versicolor; Microorganisms that degrade materials include Aspergillus niger, Aspergillus terreus, Aureobasidium pullulans, Chaetomium globosum, Cladosporium cladosporioides, Eurotium tonophilus, Fusarium moniliforme, Gliocladium virens, Myrothecium verrucaria, Penicillium citrinum, Penicillium funiculosum, and Rhizopus. oryzae et al.

[0062] The compound of the present invention represented by formula (1) above can also be used to control pests that damage or weaken trees in natural forests, planted forests, and urban green spaces. Specific examples of pests include the following:

[0063] The order Lepidoptera of the phylum Arthropoda, class Insecta, for example, Lymantriidae species such as Calliteara argentata, Euproctis pseudoconspersa, Orygia recens approximans, Euproctis subflava, and Lymantria dispar; Lasiocampidae species such as Malacosoma neustria testacea, Dendrolimus spectabilis, and Dendrolimus superans; Pyralidae species such as Crytoblabes loxiella; Noctuidae species such as Agrotis segetum; Tortricidae species such as Ptycholoma lecheana circumclusana and Cydia Adults, larvae, and eggs of species such as *Cydia cryptomeriae*, *Spilosoma imparilis* and *Hyphantria cunea* from the Arctiidae family, *Stigmella castanopsiella* from the Stigmellaceae family, and *Parasa lepida*, *Scopelodes contracus*, and *Microleon longipalpis* from the Limacodidae family;Coleoptera, for example, the Scarabaeidae family (Anomala rufocuprea, Heptophylla picea, etc.), the Buprestidae family (Agrilus spinipennis, etc.), the Cerambycidae family (Monochamus alternatus, etc.), the Chrysomelidae family (Basilepta pallidula, etc.), the Curculionidae family (Scepticus griseus, Shirahoshizo insidiosus, etc.), the Curculionidae family (Sipalinus gigas, etc.), the Bark Beetleidae family (Tomicus piniperda, Indocryphalus, etc.) Adults, larvae, and eggs of species such as Rhizopertha dominica (a type of long-horned beetle) of the family Rhizoperthidae;

[0064] Adults, larvae, and eggs of species in the order Hemiptera, such as the fir aphid (Cinara todocola) of the family Aphididae, the Yezo pine aphid (Adelges japonicus) of the family Aphididae, the Japanese cedar scale insect (Aspidiotus cryptomeriae) of the family Coccidae, and the horned scale insect (Ceroplastes ceriferus) of the family Coccidae; Adults, larvae, and eggs of Hymenoptera, such as the larch sawfly (Pachynematus itoi) of the Tenthredinidae family, the pine sawfly (Neodiprion sertifer) of the Tenthredinidae family, and the chestnut gall wasp (Dryocosmus kuriohilus) of the Gall Wasp family; adults, larvae, and eggs of Diptera, such as the crane fly (Tipula aino) of the Tipulidae family, the larch seed fly (Strobilomyia laricicola) of the Entomidae family, and the cedar gall midge (Contarinia inouyei) and the pine gall midge (Contarinia matsusintome) of the Gall Midge family; Adults, larvae, and eggs of mites belonging to the order Acari of the class Arachnida, such as the Japanese spider mite (Oligonichus hondoensis) and the fir spider mite (Oligonichus ununguis); Phylum Nematoda, Class Phantomoidea, Order Tyrenxida, for example, the pine wood nematode (Bursaphelenchus xylophilus) of the family Parasitaphelenchida.

[0065] The compound of the present invention, represented by formula (1) above, can also be used to prevent, treat, or control arthropods, nematodes, trematodes, tapeworms, and protozoa that parasitize vertebrates, especially warm-blooded vertebrates such as cattle, sheep, goats, horses, pigs, poultry, dogs, cats, and fish, either internally or externally. In addition to the above, the target animal species also include rodents such as mice, rats, hamsters, and squirrels, carnivores such as ferrets, and birds such as ducks and pigeons, as well as pets and laboratory animals. Specific examples of harmful organisms include the following:

[0066] The order Diptera (flies) of the class Insecta (arthropoda), for example, the families Tabanidae (horseflies) such as Tabanus rufidens and Tabanus chrysurus, the families Muscidae (houseflies) such as Musca bezzii, Musca domestica, and Stomoxys calcitrans, the families Botmidae (bot flies) such as Gasterophilus intestinalis, the families Bovidae (cattle flies) such as Hypoderma bovis, the families Oestridae (sheep flies) such as Oestrus ovis, the families Calliphoridae (black blowflies) such as Aldrichina grahami, the families Phoridae (large phorid flies) such as Megaselia spiracularis, and the families Sepsis (spotted phorid flies). Adults, larvae, and eggs of various mosquito species, including *Telmatoscopus albipunctatus* and *Psychoda alternata* of the family Mothflies, *Culex pipiens molestus*, *Culex pipiens pallens*, *Anopheles sinensis*, *Culex pipiens triaeniorhynchus summorosus*, and *Aedes albopictus* of the family Culicidae, *Simulium iwatense* and *Prosimulium yezoense* of the family Blackflies, and *Culicoides schulzei* and *Culicoides arakawae* of the family Bitridae; Adults, larvae, and eggs of fleas of the order Lepidomorpha, such as the cat flea (Pulex irritans) and dog flea (Ctenocephalides canis) of the family Hominidae;

[0067] Adults, larvae, and eggs of lice of the order Lice, such as the pig louse (Haematopinidae suis), the cow louse (Haematopinidae eurysternus), the horse louse (Damalinia bovis), the cow louse (Linognathus vituli), and the chicken louse (Menopon gallinae); The order Acari of the class Arachnida, phylum Arthropoda, for example, Varroa jacobsoni of the family Varroa, Haemaphysalis longicornis, Ixodes ovatus, Boophilus microplus, Amblyomma testudinarium of the family Ixodes, Ornithonyssus sylvialum of the family Ornithonyssidae, Dermanyssus gallinae of the family Demodex phylum Demodecidae, Sarcoptes scabiei bovis and Knemidocoptes mutans of the family Sarcoptidae, and Otodectes cynotis of the family Otodectes Adults, larvae, and eggs of mites such as *Cynotis* and *Psoroptes communis*; Caterpillars of the order Cyclozoa, class Bipolaria, phylum Nematoda, e.g., hookworms, kidney worms, lungworms, trichomycosis, bovine tuberculosis, etc.

[0068] Ascarids, for example, pig roundworms, chicken roundworms, etc. Phylum Platyhelminthes, Class Trematodea, for example, Schistosoma japonicum, Hepatitis biwae, Paragonimus westermani, Paragonimus leucocarpus, etc. Classes of tapeworms, such as tapeworms, tapeworms, tapeworms, tapeworms, tapeworms, ringworms, etc.: Phylum Protistata, Class Flagellates: Order Rhizoflagellates (e.g., Histomonas), Order Protoflagellates (e.g., Leishmania, Trypanosoma), Order Polyflagellates (e.g., Giardia), Order Trichomonadaceae (e.g., Trichomonas): Amoebidae, a class of fleshy organisms, such as Entamoeba; The subclass Pyroplasma of the class Sporozoa, e.g., Theilaria, Babesia, etc., and the subclass Late Sporozoa, e.g., Eimeria, Plasmodium, Toxoplasma, etc.

[0069] The compound of the present invention represented by formula (1) above can be used to exterminate pests that cause direct harm or discomfort to the human body, or to maintain public health conditions against pests that transport or transmit pathogens. Specific examples of pests include the following: Adults, larvae, and eggs of the Lepidoptera order, class Insecta, phylum Arthropoda, such as the white-tailed tussock moth (Sphrageidus similis) of the Lymantriidae family, the oak gypsy moth (Kunugia undans) of the Lasiocampidae family, the green slug moth (Parasa consocia) of the Limacodidae family, and the bamboo grass moth (Artona martini) of the Zygaenidae family; Adults, larvae, and eggs of beetles in the order Coleoptera, such as the blue longhorn beetle (Xanthochroa waterhousei) of the family Cerambycidae, the bean blister beetle (Epicauta gorhani) of the family Meloidae, and the green rove beetle (Paederus fuscipes) of the family Staphylinidae; Adults, larvae, and eggs of Hymenoptera, such as the yellow hornet (Vespa simillima xanthoptera) of the family Vespidae, the large ant (Brachyponera chinensis) of the family Formicidae, and the yellow-banded hornet (Batozonellus annulatus) of the family Sphecidae;

[0070] Adults, larvae, and eggs of flies of the order Diptera, such as the large black mosquito (Armigeres subalbatus) of the Culicidae family, the Japanese midge (Culicoides nipponensis) of the Midgeidae family, the striped midge (Chironomus yoshimatsui) of the Chironomidae family, the large black fly (Simulium nikkoense) of the Black Fly family, the green horsefly (Hirosia humilis) of the Staphidae family, the housefly (Musca domestica) of the Muscidae family, the small housefly (Fannia canicularis) of the Ichneumonidae family, the black blowfly (Phormia regina) of the Calliphoridae family, and the flesh fly (Sarcophaga peregrina) of the Sarcophagidae family; Adults, larvae, and eggs of fleas, such as the hominid flea (Pulex irritans) of the family Hominidae; Cockroaches of the order Blattodea, such as the German cockroach (Blattella germanica) of the family Blattidae, and the American cockroach (Periplaneta americana), the Oriental cockroach (Periplaneta fuliginosa), and the Japanese cockroach (Periplaneta japonica) of the family Blattidae, including adults, larvae, and eggs; Adults, larvae, and eggs of grasshoppers (Orthoptera), such as the spotted camel cricket (Diestrammena japonica) and the camel cricket (Diestrammena apicalis) of the family Cicadidae; Adults, larvae, and eggs of lice of the order Psidiophoridae, such as head lice (Pediculus humanus humanus) of the family Psidiophoridae, and pubic lice (Phthirius pubis) of the family Psidiophoridae; Adults, larvae, and eggs of the order Hemiptera, such as the bed bug (Cimex lectularius) of the family Cordyceps, and the assassin bug (Isyndus obscurus) of the family Reduviidae;

[0071] Adults, larvae, and eggs of springtails (Collembola) of the class Paracentea, phylum Arthropoda, such as Hypogastrura communis of the family Hypogastridae; Adults, larvae, and eggs of mites in the order Acari of the class Arachnida, phylum Arthropoda, such as Ixodes persulcatus of the family Ixodes, Ornithonyssus bacoti of the family Ornithonysidae, Chelacaropsis moorei of the family Cheyletidae, Pyemotes ventricosus of the family Pyemocaridae, Demodex folliculorum of the family Demodecticidae, Dermotophagoides pteronyssinus of the family Dust mite, Sarcoptes scabiei of the family Sarcoptidae, and Trombicula akamushi of the family Scrub Typhidae; Adults, larvae, and eggs of species in the order Araneae, such as Chiracanthium japonicum of the family Sparassidae, Heteropoda venatoria of the family Sparassidae, Spermophora senoculata and Pholcus phalangioides of the family Cephalidae, Uroctea compactilis of the family Uroctea compactilis, and Plexippus paykulli and Plexippus adansoni of the family Salticidae; Adults, larvae, and eggs of scorpions of the order Scorpionae, such as the spotted scorpion (Isometrus europaeus) of the family Buthidae;

[0072] Adults, larvae, and eggs of centipedes in the order Scolopendromorpha, class Chilopoda, phylum Arthropoda, such as Scolopendra subspinipes mutilans and Scolopendra subspinipes japonica of the family Scolopendridae; Adults, larvae, and eggs of centipedes such as the house centipede (Thereuronema hilgendofi) of the family Scutigeridae; Adults, larvae, and eggs of millipedes such as Oxidus gracilis of the family Oxididae, belonging to the order Diplopoda of the phylum Arthropoda; Adults, larvae, and eggs of isopoda, a class of crustaceans in the phylum Arthropoda, such as woodlice (Porcellio scaber) of the family Isopodidae; The order Gnathids of the class Leviida, phylum Annelida, for example, the land leech (Haemadipsa zeylanica japonica) of the family Hyloelidae; Fungi such as Trichophyton rubrum and Trichophyton mentagrophytes (dermatophytes), Candida albicans (Candida fungi), and Aspergillus fumigatus (Aspergillus fungi); Gram-negative bacteria such as Escherichia coli and Pseudomonas aeruginosa; and Gram-positive bacteria such as Staphylococcus aureus.

[0073] The compounds of the present invention represented by formula (1) are of particular value in controlling pests that damage crops, trees in natural forests, plantations, and urban green spaces, such as arthropods, gastropods, nematodes, and fungi. In such situations, the compounds of the present invention may also exist in their commercially useful formulations and in forms of use prepared by these formulations, as mixtures with other active compounds, such as insecticides, acaricides, nematicides, fungicides, synergists, plant growth regulators, poison baits, or herbicides. The formulations can include wettable powders, wettable granules, dry flowables, water-soluble powders, emulsions, liquids, oils, suspensions in water, emulsions in water, oily suspensions, capsules, powders, granules, fine granules, baits, tablets, sprays, fogging agents, aerosols, etc. To create these formulations, various pesticide additives that have been conventionally used in the field of agricultural and horticultural pesticides can be used as appropriate. Such pesticide additives can be used, for example, to improve the effectiveness, stability, and dispersibility of agricultural and horticultural pesticides.

[0074] Examples of pesticide adjuvants include carriers (diluents), emulsifiers, wetting agents, dispersants, and disintegrants. Examples of liquid carriers include water, aromatic hydrocarbons such as toluene and xylene, alcohols such as methanol, butanol, and glycol, ketones such as acetone, amides such as dimethylformamide, sulfoxides such as dimethyl sulfoxide, methylnaphthalene, cyclohexane, animal and vegetable oils, and fatty acids. Examples of solid carriers include clay, kaolin, talc, diatomaceous earth, silica, calcium carbonate, montmorillonite, bentonite, feldspar, quartz, alumina, sawdust, nitrocellulose, starch, and gum arabic. Conventional surfactants can be used as emulsifiers and dispersants. For example, anionic surfactants such as sodium sulfate of higher alcohols, stearyltrimethylammonium chloride, polyoxyethylene alkylphenyl ether, and lauryl betaine, as well as cationic surfactants, nonionic surfactants, and amphoteric surfactants, can be used. Additionally, wetting agents such as dialkyl sulfosuccinates; fixing agents such as carboxymethylcellulose and polyvinyl alcohol; and disintegrants such as sodium ligninsulfonate and sodium lauryl sulfate can be used. Of course, the compounds of the present invention can be incorporated as active ingredients, either individually or in combination of two or more. The content of the compounds of the present invention as active ingredients in these formulations is, for example, 0.01 to 99.5% by mass, preferably selected from the range of 0.5 to 90% by mass, and can be appropriately determined depending on various conditions such as the formulation form and application method. For example, powder formulations can be manufactured to contain about 0.5 to 20% by mass, preferably 1 to 10% by mass; wettable powders about 1 to 90% by mass, preferably 10 to 80% by mass; and emulsions about 1 to 90% by mass, preferably 10 to 40% by mass of the active ingredient.

[0075] To control arthropods, gastropods, nematodes, and fungi, the treatment can be applied to the stems and leaves of plants in areas where damage from these pests is occurring or likely to occur. In addition, it can be used by mixing it into the entire soil layer, applying it in furrows, mixing it into the bedding soil, treating seedling cells, treating planting holes, treating the base of plants, as a top dress, treating rice trays, or applying it to the water surface, allowing it to be absorbed by the roots. It can also be used by soaking seeds in the chemical, coating seeds with powder, treating with Calper, applying it to nutrient solutions in hydroponic cultivation, fumigating, or injecting it into tree trunks. When using the treatment, the amount of active ingredient should vary depending on the type and amount of pests, as well as the type of crop / tree, cultivation method, and growth stage, but generally, 0.1 to 1000 g, preferably 1 to 100 g, of the active ingredient per 10 ares should be applied. To treat this, wettable powders, granular wettable powders, dry flowable powders, water-soluble powders, emulsions, liquids, water suspensions / emulsifiers, oily suspensions, capsules, etc., should be diluted with water and sprayed on crops, etc., at a rate of 10 to 1000 liters per 10 ares, although this varies depending on the type of plant, cultivation method, and growth stage. For powders, sprays, or aerosols, the product should be applied to crops, etc., in its original formulation form.

[0076] When the target pests primarily damage plants in the soil, or when the pests are to be absorbed through the roots, possible application methods include, for example, applying the formulation diluted in water or undiluted to the base of the plant or to a seedling bed; scattering granules around the base of the plant or to a seedling bed; scattering powder, wettable powder, wettable granules, or granules before sowing or transplanting and mixing them with the entire soil; and scattering powder, wettable powder, wettable granules, granules, or fine granules in planting holes or furrows before sowing or planting the plants. Wettable powders, granular wettable powders, water-soluble powders, emulsions, liquids, water suspensions / emulsifiers, oily suspensions, capsules, etc. should be diluted with water and generally applied at a rate of 5 to 500 liters per 10 ares, spreading evenly over the entire area to be treated by spraying on the soil surface or drenching into the soil. Powders, granules, fine granules, baits, etc. should be sprayed evenly over the entire area to be treated in their original form on the soil surface. Spraying or drenching may also be done around seeds or crops / trees that you want to protect from damage. Additionally, tilling can be done during or after spraying to mechanically disperse the active ingredient.

[0077] The method of application to rice seedling trays may vary depending on the application timing, such as application at sowing, greening, or transplanting. However, it is acceptable to apply it in various forms, such as powder, wettable granules, granules, fine granules, emulsions, or suspensions in water. It can also be applied by mixing it with the growing medium. This can be done by mixing the growing medium with the powder, wettable granules, granules, or fine granules, for example, by mixing it into the bedding soil, the covering soil, or the entire growing medium. Alternatively, the growing medium and the various formulations can simply be applied in alternating layers. For application to paddy fields, solid formulations such as jumbo formulations, pack formulations, granules, and wettable granules, as well as liquid formulations such as emulsions and suspensions in water, are usually scattered onto flooded paddy fields. In addition, at the time of rice planting, a suitable formulation can be applied directly or mixed with fertilizer and scattered or injected into the soil. Furthermore, by using liquid formulations such as emulsions and suspensions in water at the water inlet or irrigation system that leads to water supply, application can be carried out in a labor-saving manner. Methods of seed treatment include, for example, immersing seeds in a diluted or undiluted liquid formulation to allow the agent to adhere and penetrate; mixing a solid or liquid formulation with the seeds, coating them with a powder to adhere to the seed surface; coating the seeds with an adhesive carrier such as a resin or polymer; and spraying the formulation near the seeds at the same time as planting. The "seeds" to be treated in this manner refer to plant bodies in the early stages of cultivation used for plant propagation, and include, for example, seeds, bulbs, tubers, seed potatoes, buds, bulbils, or plant bodies used for vegetative propagation by cuttings. Furthermore, when referring to the "soil" or "cultivation support" for plants when applied, it means a support for cultivating crops, especially a support for root growth. The material is not particularly limited, but any material on which plants can grow is acceptable, and may include so-called soil, seedling mats, water, etc. Specific materials include, for example, sand, pumice, vermiculite, diatomaceous earth, agar, gel-like substances, polymer substances, rock wool, glass wool, wood chips, bark, etc. For the sowing or seedling stage of plants to be transplanted, in addition to direct treatment of the seeds, it is preferable to apply a liquid fungicide to the seedling bed or to scatter granular fungicide. It is also preferable to apply granular fungicide to the planting hole at the time of transplanting, or to mix it with the cultivation carrier near the transplanting site.

[0078] The compound of the present invention represented by formula (1) is also valuable for protecting wood (standing trees, fallen trees, processed wood, stored wood, or structural wood) from damage caused by insects such as termites or beetles, and fungi. In such situations, control can be achieved by spraying, injecting, drenching, or coating oils, emulsions, wettable powders, or suspensions in water onto the wood or the surrounding soil, or by spraying powders, granules, etc. Furthermore, the oils, emulsions, wettable powders, powders, etc. used in this context can also exist as mixtures with other active compounds, such as insecticides, acaricides, nematicides, fungicides, repellents, synergists, etc. These formulations may contain the active ingredient compound in a total amount of 0.0001 to 95% by mass, preferably 0.005 to 10% by mass for oils, powders, granules, etc., and 0.01 to 50% by mass for emulsions, wettable powders, suspensions in water, etc. When controlling arthropods, fungi, etc., 1m 2 Apply 0.01 to 100 g of the active ingredient compound per unit area to the soil or wood surface.

[0079] The compound of the present invention, represented by formula (1) above, can be used to protect grains, fruits, nuts, spices, tobacco, and other products from damage by lepidopterans, beetles, mites, and fungi when stored in their original state, in powdered state, or mixed into other products. It can also protect animal products (hides, hair, wool, feathers, etc.) and plant products (cotton, paper, etc.) from attacks by lepidopterans, beetles, silverfish, and cockroaches when stored in their natural or transformed state, and further protect food products such as meat and fish from attacks by lepidopterans, beetles, flies, and mites when stored. In such situations, control can be achieved by methods such as spraying oils, emulsions, wettable powders, or powders; installing resin vaporizers; treating with fumigants or aerosols; installing granules, tablets, or poisoned bait; or spraying aerosols. Furthermore, these formulations can also exist as mixtures with other active compounds, such as insecticides, acaricides, nematicides, fungicides, repellents, and synergists, and these formulations may contain a total amount of active ingredient compounds ranging from 0.0001% to 95% by mass.

[0080] The compound of the present invention, represented by formula (1) above, is valuable for the extermination or prevention of arthropods that parasitize the body surface of humans and livestock and cause direct harm such as feeding on the skin or sucking blood, as well as fungi, arthropods that spread diseases in humans and livestock or act as vectors for such diseases, and arthropods that cause discomfort to humans, such as nematodes, trematodes, tapeworms, and protozoa. In such situations, the compound of the present invention can be mixed in small amounts into food or feed, or administered orally as a suitable orally ingestible pharmaceutical composition, such as tablets, pills, capsules, pastes, gels, beverages, medicinal feeds, medicinal drinking water, medicinal supplemental feeds, sustained-release large pills, or other sustained-release devices that remain in the gastrointestinal tract, or administered transdermally as a spray, powder, grease, cream, ointment, emulsion, lotion, spot-on, pour-on, shampoo, etc. To achieve the desired effect in such applications, the formulation generally contains 0.0001 to 0.1% by mass, preferably 0.001 to 0.01% by mass, of the active ingredient compound. Furthermore, for transdermal or local administration, devices attached to animals (e.g., collars, medallions, ear tags, etc.) can be used to locally or systemically control arthropods.

[0081] The following describes specific oral and transdermal administration methods for using the compound of the present invention represented by formula (1) as an anthelmintic for animals such as livestock and pets, or for humans, but the invention is not necessarily limited to these methods. When administered orally as a medicinal beverage, the beverage is usually a solution, suspension, or dispersion in a suitable non-toxic solvent or water, along with a suspending agent such as bentonite, a wetting agent, or other excipient. Generally, the beverage also contains an antifoaming agent. The beverage formulation generally contains 0.01 to 1.0% by mass, preferably 0.01 to 0.1% by mass, of the active ingredient compound. When oral administration in a dry, solid form is preferred, capsules, pills, or tablets containing a predetermined amount of the active ingredient are typically used. These forms are manufactured by appropriately grinding 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 allow for a wide range of variations in the mass and content of the anthelmintic depending on the type of host animal being treated, the degree of infection, the type of parasite, and the host's body weight.

[0082] When administered via animal feed, it can be homogeneously dispersed in the feed, used as a top dressing, or in pellet form. Generally, to achieve the desired antiparasitic effect, the final feed should contain 0.0001 to 0.05% by mass, preferably 0.0005 to 0.01% by mass, of the active ingredient compound. The active compound, when dissolved or dispersed in a liquid carrier excipient, can be administered parenterally to animals by intragumic, 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 mass, preferably 0.1 to 5.0% by mass, of the active ingredient compound. It can also be administered topically by mixing it with a suitable carrier such as dimethyl sulfoxide or a hydrocarbon solvent. This formulation is applied directly to the external surface of an animal by spray or direct injection. Furthermore, the compound of the present invention represented by formula (1) can also be used as an insecticide for arthropods that directly cause harm or arthropods that transmit diseases, etc., in the surrounding environment where such pests may be present, by methods such as spraying, injecting, drenching, or coating oils, emulsions, or wettable powders; spraying powders, etc.; treatment with fumigants, heated fumigants such as mosquito coils, self-combusting fumigants, or chemical reaction fumigants; fogging; treatment with ULV agents, etc.; setting up granules, tablets, or poison bait; or adding floating powders, granules, etc., to waterways, wells, reservoirs, water tanks, and other flowing or stagnant water. In addition, it is possible to control tussock moths, which are also agricultural and forest pests, in the same way as described above, or for flies, etc., by mixing it into livestock feed so that it mixes with their feces, and for mosquitoes, etc., by volatilizing it into the air with electric mosquito traps, etc. These formulations, in their various forms of use, can also exist as mixtures with other active compounds, such as pest control agents, mite control agents, nematode control agents, disease control agents, repellents, and synergists. These formulations contain a total amount of the active ingredient compound ranging from 0.0001% to 95% by mass.

[0083] The compound of the present invention represented by formula (1) can also be used in combination with other active compounds as a mixed agent. In particular, by using it in combination with compounds (insecticides) having pest control activity, mite control activity, or nematode control activity, it becomes possible to expand the range of pests and diseases that can be controlled for the control of arthropods, gastropods, nematodes, and other harmful organisms that damage plants, and synergistic effects such as a reduction in the amount of pesticide can also be expected. Specific examples of such active compounds include the following.

[0084] Organophosphorus compounds, for example, acephate, azinphos-methyl, chlorpyrifos, diazinon, dichlorvos, dimeton-S-methyl, dimethoate, dimethylvinphos, disulfoton, ethion, fenitrothion, fenthion, isoxathion, malathion, methamidophos, methidathion, monophosphorus Crotophos, naled, oxideprofos, parathion, phenthoate, phosalone, pirimiphos-methyl, pyridafenthion, profenofos, prothiofos, propaphos, pyraclofos, salition, sulprofos, thiometon, tetrachlorvinfos, trichlorphon, vamidothion, etc. Carbamates, for example, alanicarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, furathiocarb, isoprocarb, methomyl, metolcarb, pirimicarb, propoxur, thiodicarb, etc. Organochlorine agents, such as aldrin, chlordane, DDT (p,p'-DDT), endosulfan, lindane, etc.

[0085] Pyrethroids, for example, acrinathrin, allethrin, bifenthrin, cycloprothrin, cyfluthrin, cyhalothrin, cyphenothrin, cypermethrin, deltamethrin, etofenprox, fenpropathrin, fenvalerate, and flucythrinate. Flufenprox, fluvalinate, furamethrin, halfenprox, imiprothrin, permethrin, phenothrin, prallethrin, pyrethrins, resmethrin, silafluofen, tefluthrin, tralomethrin, transfluthrin, etc. Neonicotinoid drugs, such as acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, etc.

[0086] Diamides, such as chlorantraniliprole, cyantraniliprole, cyclaniliprole, flubenziamide, and tetraniliprole; Phenylpyrazole preparations, such as ethiprole, fipronil, acetoprole, pyrafluoprole, and pyriplore; Nereistoxins, such as bensultap, cartap, thiocyclam, thiosultap, etc. Insect growth regulators such as phenylbenzoylureas and diacylhydrazines, for example, chlorfluazuron, diflubenzuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron, buprofezin, chromafenozide, halofenozide, methoxyfenozide, tebufenozide, cyromazine, etc. Juvenile hormone preparations, such as diofenolan, fenoxycarb, hydroprene, mesoprene, and pyriproxyfen;

[0087] Insecticidal substances produced by microorganisms, such as abamectin, emamectin-benzoate, ivermectin, lepimectin, milbemectin, nemadectin, nikkomycin, polioxin complex, spinetram, spinosad, and BT agents; Insecticides derived from natural products, such as anabasine, azadiractin, deguelin, decanolyoctanoylglycerol, hydroxypropyl starch, soy lecithin, nicotine, nornicotine, sodium oleic acid salt, petroleum oil, propylene glycol monolaurate, rapeseed oil, rotenone, sorbitan fatty acid ester, starch, etc. Other insecticides include, for example, afidpyropen, benzpyrimoxan, broflanilide, chlorfenapyr, diafenthiuron, dichloromezotiaz, dimpropyridaz, and DBEDC (Dodecylbenzenesulfonic acid bisethylenediamine copper [II]). salt), flonicamid, flometoquin, flufenerim, flupyradifurone, flupyrimin, fluralaner, fluhexafon, fluxametamide, hydramethylnon, indoxacarb, isocycloseram, metaflumizone, metaldehyde, nicotine sulfate sulfate, oxazosulfyl, pymetrozine, pyridalyl, pyrifluquinazone, spirotetramat, sulfoxaflor, tolfenpyrad, trizamate, triflumezopyrim, tyclopyrazoflor, etc.

[0088] Acaricides, for example, acequinocyl, acynonapyr, amidoflumet, amitraz, azocyclotin, benzoximate, bifenazate, binapacryl, phenisobromolate, chinomethionate, clofentezine, cyenopyrafen, cyflumetofen, tricyclohexyltin hydroxide, dicofol, dienochlor, ethoxazole, fenazaflor, fenazaquin, fenbutatin oxide Examples include oxide, fenothiocarb, fenpyroximate, fluacrypyrim, hexythiazox, pyrimidifen, polynactins, propargite, pyflubumide, pyridaben, spirodiclofen, spiropidion, spiromesifen, tebufenpyrad, tetradifon, and flupentiofenox: Nematicides, such as aluminum phosphide, benclothiaz, cadusafos, etoprophos, fluazaindolizine, fluensulfone, fosthiazate, furfural, imicyafos, levamisol hydrochloride, mesulfenfos, metam-ammonium, methyl isothiocyanate, morantel tartarate, oxamyl, thioxazafen, etc. Poisonous baits include, for example, chlorphacinone, coumatetralyl, diphacinone, sodium fluoracetate, and warfarin.

[0089] The compound of the present invention represented by formula (1) can also be used as a mixture with other active compounds other than those having pest control activity, mite control activity, or nematode control activity. By using it in mixture with compounds having fungicidal activity, herbicidal activity, or plant growth regulating activity to control diseases and / or weeds that occur simultaneously during the period of application, synergistic effects such as reduced control labor and reduced dosage can be expected. Furthermore, by using it in mixture with repellents, synergists, etc., more effective control effects such as synergistic effects can be expected.

[0090] Specific examples of active compounds include disease control agents such as DD (1,3-dichloropropene), acibenzolar-S-methyl, aldimorph, ametoctradin, amisulbrom, andoprim, anilazine, azaconazole, azoxystrobin, basic copper sulfate, benodanil, benomyl, benthiavalicarb-isopropyl, benthiazole, bitertanol, bixafen, blasticidin S, boscalid, bromuconazole, and calcium carbonate. carbonate, butthiobate, calcium polysulfide, captafol, captan, carbendazim, carboxin, carpropamid, chinomethionate, chlorfenazole, chloroneb, chloropicrin, chlorothalonil, chlorozolinate, DBEDC (complex of bis(ethylenediamine)copper-bis-(dodecylbenzenesulfonic acid)),

[0091] Copper hydroxide, copper nonylphenol sulfonate, basic copper chloride, cyazofamide, cyflufenamid, cymoxanil, cyproconazole, cyprodinil, dazomet, diclobutrazol, dichlofluanid, dichlone, diclocymet, diclomezine, diethofencarb, difenoconazole, diflumetrim torim), dimethomorph, dimoxystrobin, diniconazole, diniconazole-M, dithane-stainless, dithianon, dodine, eclomezole, edifenphos, enestrobin, epoxyconazole, etaconazole, etaboxam, extract from mushroom, famoxadone, fenamidone, fenarimol, fenbuconazole, fenfuram, fenhexamid,

[0092] Fenoxanil, fenpiclonil, fenpropidin, fenpyrazamine, ferimzone, fluazinam, flumetover, flumorph, fluopicolide, fluopyram, fluoroimide, fluotrimazole, fluoxastrobin, fluquinconazole, flusulfamide, flutolanil, flux Fluxapyroxad, folpet, fosetyl-AL, fthalide, fuberidazole, fludioxonil, flusilazole, flutianil, flutriafol, furametpyr, furconazole, guazatine, hexaconazole, hydroxyioxazole, hymexazol, imazalil, imazalil sulfate sulfate), imibenconazole, iminoctadine acetate, iminoctadine-DBS, ipconazole,

[0093] IBP (iprobenfos), iprodione, iprovalicarb, isofetamide, isoprothiolane, isopyrazam, isotianil, kasugamycin, kresoxim-methyl, mancozeb, mandipropamid, maneb, manzeb, mepanipyrim, mepronil, metalaxyl, metam-ammonium, metam-sodium, metconazole, metasulfocarb, methyl bromide bromide, methylisothiocyanate, metominostrobin, metrafenone, mildiomycin, myclobutanil, nickel dimethyldithiocarbamate, nuarimol, orysastrobin, oxadixyl, oxathiapiprolin, oxine-copper, oxolinic acid, oxpoconazole fumarate fumarate, oxycarboxin, oxytetracycline, pebulate, pefurazoate, penconazole, pencycuron, penflufen, penthiopyrad, picarbutrazox, picoxystrobin,

[0094] Piperalin, polycarbamate, polyoxin-B, polyoxins, potassium hydrogen carbonate, probenazole, prochloraz, procymidone, propamocarb, propiconazole, propineb, proquinazid, prothioconazole, pyraclostrobin ), pyrametostrobin, pyraoxystrobin, pyrazophos, pyribencarb, pyridinitril, pyrifenox, pyrimethanil, pyriophenone, pyroquilon, quinoxyfen, quintozene, sedaxane, silver, simeconazole, sodium hydrogen carbonate, sodium hypochlorite(hypochlorite), spiroxamine, streptomycin, sulfur, tebfloquin, tebuconazole, tecloftalam, terbinafine, tetraconazole, thiabendazole, thiadiazin, tifluzamide, thiophanate, thiophanate-methyl, thiram, tiadinil, tolclofos-methyl Examples include yl), tolprocarb, tolylfluanid, triadimefon, triadimenol, triclopyricarb, tricyclazole, tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole, uniconazole-P, validamycin(-A), vinclozolin, zarilamid, zinc sulfate, zineb, ziram, and zoxamide.

[0095] Examples of compounds with herbicidal activity include acronifen, acifluofe n-sodium, alachlor, alloxydim, amicarbazone, amidosulfuron, anilofos, asulam, atrazine, azimsulfuron, benfuresate, bensulfuron-methyl, bentazone, benthiocarb, benzobicyclon, benzofenap, bialaphos, and bifenox. Bromobutide, bromoxynil, butamifos, cafenstrole, calcium peroxide(peroxide), carbetamide, cinosulfuron, clomeprop, cyclosulfamuron, cyhalofop-butyl, daimuron, desmedipham, diclofop-methyl, diflufenican, dimefuron, dimethametryn, dinoterb, diquat Diquat, Diuron, Esprocarb, Ethiozin, Ethofumesate, Ethoxysulfuron, Etobenzand, Fenoxaprop-P-ethyl, Fentrazamide, Flucarbazone, Flufenacet, Flurtamone, Fluthiacet-methyl foramsulfuron, glufosinate-ammonium, glyphosate-isopropylamine, glyphosate-trimesium, imazapyr, imazosulfuron, indanofan,

[0096] Iodosulfuron, ioxynil-octanoate, isoproturon, isoxadifen, isoxaflutole, lactofen, linuron Mefenacet, mesosulfuron, metamitron, metabenzthiazuron, metosulam, metribuzin, nappropamide, neburon, oxadiargyl, oxadiazon, oxaziclomefone, paraquat, pendimethalin, pentoxazone, phenmedipham, pretilachlor, propoxycarbazone, prosulfocarb, pyraclonil, pyraflufenethyl Examples include n-ethyl, pyrazolate, pyrazosulfuro n-ethyl, pyributicarb, pyriftalid, pyriminobac-methyl, quizalofop-ethyl, sethoxydim, simazine, sulcotrion, sulfentrazone, thenylchlor, triaziflam, and tribufos.

[0097] Furthermore, compounds that have plant growth regulating effects include, for example, 1-naphthylacetamide, 4-CPA, 6-benzylaminopurine, butralin, calcium chloride, calcium formate, calcium peroxide, calcium sulfate, chlormequat chloride, choline, cyanamide, cyclanilide, daminozide, decyl alcohol, dichjoprop, ethephon, etychlozate, flurprimidol, forchlorfenuron, and gibberellin. It can also be used in combination with substances such as acid, indolebutyric acid, maleic hydrazide potassium salt, mefenpyr, mepiquat chloride, oxine sulfate (8-hydroxyquinoline sulfate), paclobutrazol, paraffin, prohexadione-calcium salt, prohydrojasmon, thidiazuron, trinexapac ethyl, uniconazole-P, wax, etc. Repellents, e.g., capsaicin, carane-3,4-diol, citronellal, DEET, dimethyl phthalate, hinokitiol, limonene, linalool, menthol, menthone, naphthalene, thiram, etc.; synergists, e.g., methylenedioxynaphthalene, naphthyl propynyl ether, nitrobenzyl thiocyanate, octachlorodipropyl ether, pentynyl phthalimide, phenyl salioxone Examples include salioxon, piperonyl butoxide, safrole, sesamex, sesamin, sulfoxide, triphenyl phosphate, and verbutin.

[0098] The compounds of the present invention are used as biopesticides for, for example, viral preparations such as cytoplasmic polyhedrosis virus (CPV), entomopox virus (EPV), granulosis virus (GV), nuclear polyhedrosis virus (NPV), Beauveria bassiana, Beauveria brongniartii, Monacrosporium phymatophagum, Paecilomyces fumosoroseus, Pasteuria penetrans, Steinernema carpocapsae, and Steinernema glacerai. Microbial pesticides used as insecticides or nematodeicides for insects such as glaseri, Steinernema kushidai, and Verticillium lecanii, as well as for Agrobacterium radiobacter, Bacillus subtilis, non-pathogenic Erwinia carotovora, non-pathogenic Fusarium oxysporum, Pseudomonas CAB-02, Pseudomonas fluorescens, Talaromyces flavus, and Trichoderma atroviride. Similar effects can be expected by mixing it with microbial pesticides used as fungicides, such as atroviride, Trichoderma lignorum, and biological pesticides used as herbicides, such as Xanthomonas campestris.

[0099] Furthermore, as biological pesticides, for example, Amblyseius californicus, Amblyseius cucumeris, Amblyseius degenerans, Aphidius colemani, Aphidoletes aphidimyza, Chrysoperia carnea, Dacnusa sibirica, Diglyphus isaea, Encarsia formosa, Eretmocerus eremicus, Franklinothrips vespiformis, and Harmonia axyridis. Natural enemies such as axyridis, Hemiptarsenus varicornis, Neochrysocharis formosa, Orius sauteri, Orius strigicollis, Phytoseiulus persimilis, Pilophorus typicus, and Piocoris varius, as well as codlelure, cuelure, geraniol, gyptol, liblure, looplure, and methyl eugenol. It can also be used in combination with pheromone agents such as eugenol, orfralure, peachflure, phycilure, pyrimalure, and turpentine. [Examples]

[0100] The present invention will be described in more detail below with reference to examples, formulations, and test examples, but the scope of the present invention is not limited in any way by these examples, formulations, and test examples.

[0101] Example 1 Synthesis of N,N-dimethyl-N'(1-phenylpropylidene)formhydrazoneamide (compound number: A-1), represented by the following formula A-1.

[0102] [ka] 1-1: Synthesis of (1-phenylpropylidene)hydrazine represented by the following formula

[0103] [ka]

[0104] Propiophenone (1.34 g) was dissolved in ethanol (20 mL), and hydrazine monohydrate (971 μL) was added. After heating under reflux for 3 hours, the mixture was concentrated, water was added, and the solution was extracted with ethyl acetate and washed with saturated saline. Then, after drying over sodium sulfate, the mixture was concentrated to obtain 1.53 g of a light brown oily residue. This residue was used in the next reaction without purification.

[0105] 2: Synthesis of N,N-dimethyl-N'-(1-phenylpropylidene)formhydrazoneamide (compound number: A-1) represented by the above formula A-1. (1-phenylpropylidene)hydrazine (1.00 g) was dissolved in toluene (15 mL), N,N-dimethylformamide dimethyl acetal (2.26 mL) was added, and the reaction mixture was heated under reflux for 1.5 hours. The organic solvent was removed by distillation under reduced pressure, and the residue was purified by silica gel column chromatography to obtain compound A-1 as an oily substance of 979 mg (yield 72%).

[0106] Example 2 Synthesis of methyl-N-1-phenylpropylidene)formohydrazonate (compound number: A-4) represented by the following formula A-4.

[0107] [ka]

[0108] Propiophenone (700 mg) was dissolved in ethanol (7.5 mL), and hydrazine monohydrate (0.5 mL) and acetic acid (25 μL) were added. After heating under reflux for 3 hours, water was added, and the mixture was extracted with ethyl acetate and washed with saturated saline. After drying with sodium sulfate, the mixture was concentrated to obtain a light brown oily residue. Without purification, the compound (1-phenylpropylenene)hydrazine of the present invention was dissolved in toluene (7 mL), trimethyl orthoformate (700 μL) was added, and the reaction mixture was heated under reflux for 3 hours and left to stand overnight at room temperature. The organic solvent was removed by distillation under reduced pressure, and the residue was purified by silica gel column chromatography to obtain compound A-4 as an oily substance of 206 mg (yield 21%).

[0109] Example 3 Synthesis of N'-(1-phenylpropylidene)formohydrazide (compound number: B-1), represented by the following formula B-1.

[0110] [ka]

[0111] Propiophenone (24 g) was diluted with ethanol (100 mL), formohydrazide (10 g) and acetic acid (0.25 mL) were added, and the mixture was heated under reflux for 7 hours. The reaction mixture was then allowed to stand overnight at room temperature. Half of the organic solvent was removed by distillation under reduced pressure, water was added to the residue, and the precipitated solid was collected by filtration. The solid was washed with water and n-hexane to obtain compound B-1 as a white solid of 22 g (yield 75%).

[0112] Regarding the synthesized compounds, including those produced in the same manner as in the above examples, 1The 1H-NMR data is shown in Tables 3 and 4 below. In Tables 3 and 4 below, the compound numbers correspond to those listed in Tables 1 and 2, respectively.

[0113] [Table 3]

[0114] [Table 4]

[0115] The following examples illustrate formulations containing the compounds of the present invention, but the scope of the present invention is not limited in any way by the preparation methods of these formulations. In the examples of formulations, "parts" all refer to parts by mass.

[0116] Formulation Example 1: Emulsion An emulsion was obtained by uniformly mixing and dissolving the compound of the present invention (10 parts), xylene (60 parts), N-methyl-2-pyrrolidone (20 parts), and Solpol 3005X (a mixture of a nonionic surfactant and an anionic surfactant, Toho Chemical Industry Co., Ltd., trade name) (10 parts).

[0117] Formulation Example 2: Wettable Powder The compound of the present invention (20 parts), Toxil GU-N (white carbon, Oriental Silicas Corporation) (20 parts), Solpol 5096 (polyoxyethylene styrylphenyl ether sulfate, Toho Chemical Industry Co., Ltd.) (10 parts), and SS Clay (clay, Showa KDE Co., Ltd.) (50 parts) were mixed and then ground using a pulverizer to obtain a wettable powder.

[0118] Formulation Example 3: Water-soluble The compound of the present invention (5 parts), Lunox P-65L (sodium alkylbenzene sulfonate, Toho Chemical Industry Co., Ltd.) (3 parts), and sodium bicarbonate (reagent) (92 parts) were uniformly mixed and then ground using a pulverizer to obtain an aqueous solvent.

[0119] Manufacturing Example 4: Granular Wettable Powder The compound of the present invention (20 parts), Demol N (naphthalene sulfonate formalin condensate, Kao Corporation, trade name) (5 parts), Airroll CT-1L (dioctyl sulfosuccinate, Toho Chemical Industry Co., Ltd., trade name) (1 part), Selogen 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 ground using an air mill. Water was added to this mixture and kneaded thoroughly, then extruded and granulated, and dried to obtain a granular wettable powder.

[0120] Formulation Example 5: Flowable Formulation The compound of the present invention (20 parts), Solpol 7948 (polyoxyalkylene ristyrylphenyl ether sulfate sodium, Toho Chemical Industry Co., Ltd.) (5 parts), propylene glycol (reagent) (10 parts), and water (40 parts) were pre-mixed and wet-milled 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 agent.

[0121] 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 while stirring to obtain a dispersion. To this dispersion, KELZAN (xanthan gum, Sansho Co., Ltd.) (0.2 parts), dispersed in propylene glycol (reagent) (5.0 parts), was added to obtain an emulsion formulation.

[0122] 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 sorbitan tetraoleate, Kao Corporation) (24 parts) to obtain a dispersion. This dispersion and water (50.8 parts) were dispersed in 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.

[0123] Formulation Example 8: Microemulsion A microemulsion was obtained by uniformly mixing the compound of the present invention (10 parts), xylene (reagent) (20 parts), Newcalgen D-230 (polyoxyethylene castor oil, Takemoto Oil & Fat Co., Ltd.) (20 parts), Airroll CT-1L (sodium dioctyl sulfosuccinate, Toho Chemical Industry Co., Ltd.) (2.0 parts), and water (48 parts).

[0124] Formulation Example 9: Liquid Formulation The compound of the present invention (20 parts), H-methyl-2-pyrrolidone (reagent) (70 parts), and Newcalgen D-230 (polyoxyethylene castor oil, Takemoto Oil Co., Ltd.) (10 parts) were uniformly mixed and dissolved to obtain a liquid preparation.

[0125] Formulation Example 10: Granules-1 The compound of the present invention (5 parts), Air Roll CT-1L (sodium dioctyl 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, water was added and kneaded well, then extruded and granulated, and dried to obtain granules.

[0126] Formulation Example 11: Granules-2 The compound of the present invention (5 parts) was dissolved in methanol (reagent), and then adsorbed onto Ishikawa Light No. 2 (95 parts) using a rolling granulator, dried, and granules were obtained.

[0127] Formulation Example 12: Granules - 1 Two parts of the compound of the present invention were dissolved in methanol (reagent), and then adsorbed onto 98 parts of Ishikawa Light No. 4 using a rolling granulator. The mixture was then dried to obtain fine particles.

[0128] Formulation Example 13: Granules - 2 The compound of the present invention (5 parts) and Toxil GU-N (5 parts) were mixed and then pulverized using a fine grinder, and uniformly mixed with Iide silica sand (silica sand, JFE Mineral Corporation) (80 parts). A diluted aqueous solution of Toxanone GR-31A (polycarboxylic acid type surfactant, Sanyo Chemical Industries, Ltd.) (10 parts) was sprayed onto this mixture and mixed further to obtain a granular composition. This granular composition was dried to obtain a fine particle.

[0129] Formulation Example 14: Powder The compound of the present invention (5 parts), Toxil GU-N (5 parts), and Oomori fine clay powder (clay, Oomori Sangyo Co., Ltd.) (90 parts) were uniformly mixed and then ground using a pulverizer to obtain a powder.

[0130] Formulation Example 15 DL Powder The compound of the present invention (5 parts), propylene glycol (0.5 parts), and DL clay (94.5 parts) were uniformly mixed and then pulverized using a pulverizer to obtain a powder.

[0131] Formulation Example 16: Seed Coating Powder The compound of the present invention (10 parts), PVA-117 (polyvinyl alcohol, Kuraray Trading Co., Ltd.) (1 part), and Oomori fine clay powder (89 parts) were uniformly mixed and ground using a pulverizer to obtain a powder. Pre-moistened seeds were mixed with this powder and air-dried to obtain coated seeds.

[0132] Formulation Example 17: Seed Coating Flowable Agent The compound of the present invention (10 parts), Solpol 7948 (5 parts), propylene glycol (reagent) (10 parts), and water (40 parts) were pre-mixed and wet-milled using a bead mill. Next, KELZAN (xanthan gum, Sansho Co., Ltd.) (0.2 parts) and water (29.8 parts) were thoroughly mixed and dispersed, and a gel-like substance was prepared by mixing in AMECOAT HCA / 83 (acrylic acid polymer, SOLVAY) (5 parts). The pulverized slurry and the prepared gel-like substance were thoroughly mixed to obtain a flowable agent. This flowable agent was mixed with seeds and air-dried to obtain coated seeds.

[0133] Formulation Example 18: Oily Suspension Formulation The compound of the present invention (20 parts), Newcalgen C-120 (POE tristyrylphenyl ether, Takemoto Oil & Fat Co., Ltd., trade name) (5 parts), Leodol TW-O120V (POE sorbitan monooleate, Kao Corporation, trade name) (10 parts), methyl oleate (Kanto Chemical Co., Ltd., reagent) (62 parts), and Esben NZ (organic bentonite, Hojun Co., Ltd., trade name) (3 parts) were thoroughly mixed and dispersed, and this slurry dispersion was wet-milled to obtain an oily suspension formulation.

[0134] Next, specific examples of the compounds of the present invention will be further explained by the following test examples.

[0135] Test Example 1: Insecticidal efficacy test of spray treatment against eggplant green aphid (Myzus persicae) Leaf fragments infested with 20-50 adult and larval aphids were inoculated onto the leaves of potted eggplant seedlings that had been grown for three weeks after sowing. A water-diluted emulsion (400 ppm) prepared according to Formulation Example 1 was sprayed onto the leaves and stems of the aphid-infested eggplant seedlings using an airbrush the day after inoculation. Seven days after treatment, the number of infested aphids was investigated, and the control rate was calculated according to the following formula. The experiment was conducted using one seedling from each group.

[0136] Control rate (%) = (1 - A / B × D / C) × 100 A: Number of aphid adults and larvae per seedling in the untreated area before spraying B: Number of aphid adults and larvae per seedling in the treatment plot before spraying C: Number of aphid adults and larvae per seedling in the untreated area 7 days after spraying D: Number of aphid adults and larvae per seedling 7 days after application in the treated area

[0137] As a result, the compounds of the present invention with compound numbers (A-1, A-2, A-3, A-4, and A-5) showed a control rate of 80% or more.

[0138] Test Example 2: Insecticidal efficacy test of drenching treatment against eggplant aphid (Myzus persicae Sulzer) Leaf fragments infested with 20-50 adult and larval aphids were inoculated onto the leaves of potted eggplant seedlings that had been grown for three weeks after sowing. A 400 ppm aqueous dilution of the emulsion prepared according to Formulation Example 1 was drenched at the base of the eggplant seedlings infested with aphids the day after inoculation. Seven days after treatment, the number of infested aphids was investigated, and the control rate was calculated according to the following formula. Note that the experiment was conducted using one seedling from each treatment group. Control rate (%) = (1 - A / B × D / C) × 100 A: Number of aphid adults and larvae per seedling in the untreated area before spraying B: Number of aphid adults and larvae per seedling in the treatment plot before spraying C: Number of aphid adults and larvae per seedling in the untreated area 7 days after spraying D: Number of aphid adults and larvae per seedling 7 days after application in the treated area

[0139] As a result, the compounds of the present invention with compound numbers (A-1, A-2, A-4, and A-5) showed a control efficacy of 80% or more.

[0140] Test Example 3: Insecticidal efficacy test of spray treatment against cotton aphids (Aphis gosiipii Glover) on cucumbers. Leaf fragments infested with 50-80 adult and larval aphids were inoculated onto the leaves of potted cucumber seedlings that had been grown for two weeks after sowing. A 400 ppm aqueous solution of the emulsion prepared according to Formulation Example 1 was sprayed onto the leaves and stems of the aphid-infested cucumber seedlings using an airbrush the day after inoculation. Seven days after treatment, the number of infested aphids was investigated, and the control rate was calculated according to the following formula. The experiment was conducted using one seedling from each plot.

[0141] Control rate (%) = (1 - A / B × D / C) × 100 A: Number of aphid adults and larvae per seedling in the untreated area before spraying B: Number of aphid adults and larvae per seedling in the treatment plot before spraying C: Number of aphid adults and larvae per seedling in the untreated area 7 days after spraying D: Number of aphid adults and larvae per seedling 7 days after application in the treated area

[0142] As a result, the compounds of the present invention with compound numbers (A-1, A-2, A-3, A-4, A-5, A-6, and A-7) showed a control efficacy of 80% or more.

[0143] Test Example 4: Insecticidal efficacy test of drenching treatment against cotton aphids (Aphis gosiipii Glover) on cucumbers. Leaf fragments infested with 50-80 adult and larval aphids were inoculated onto the leaves of potted cucumber seedlings that had been grown for two weeks after sowing. A 400 ppm aqueous dilution of the emulsion prepared according to Formulation Example 1 was drenched at the base of the aphid-infested cucumber seedlings the day after inoculation. Seven days after treatment, the number of infested aphids was investigated, and the control rate was calculated according to the following formula. The experiment was conducted using one seedling from each treatment group. Control rate (%) = (1 - A / B × D / C) × 100 A: Number of aphid adults and larvae per seedling in the untreated area before spraying B: Number of aphid adults and larvae per seedling in the treatment plot before spraying C: Number of aphid adults and larvae per seedling in the untreated area 7 days after spraying D: Number of aphid adults and larvae per seedling 7 days after application in the treated area As a result, the compounds of the present invention with compound numbers (A-1, A-2, A-3, A-4, A-5, A-6, and A-7) showed a control rate of 80% or more.

[0144] Test Example 5: Insecticidal efficacy test of drenching treatment against eggplant aphid (Myzus persicae Sulzer) Using aqueous dilutions (50 ppm or 12.5 ppm) of emulsions prepared according to Formulation Example 1, compounds B-1 and B-2 of the present invention, the control rate against the peach aphid was calculated according to Test Example 2. The compounds used for comparison are indicated by the following compound symbols.

[0145] [ka] Comparator A (Compound IX described in Patent Document 1)

[0146] [ka] Comparator B (Patent Document 2, No. 4)

[0147] The results obtained are shown in Table 5 below. [Table 5]

[0148] As described above, the compounds of the present invention demonstrate excellent control capabilities against aphids, even when used at low concentrations.

Claims

1. The following formula (1), 【Chemistry 1】 [In the formula, R 1 C 1-6 It shows an alkyl group, R 2 C 1-6 Alkoxy group or NR 3 R 4 Show, R 3 C 1-6 It shows an alkyl group, R 4 represents C 1-6 an alkyl group, X 1 This represents a hydrogen atom or a halogen atom. A hydrazone derivative or salt thereof, as shown by [the formula].

2. An agricultural and horticultural insecticide containing the hydrazone derivative or a salt thereof as an active ingredient, according to claim 1.

3. The following formula (2), 【Chemistry 2】 [In the formula, X 2 However, it shows a hydrogen atom, and R 5 However, it indicates a hydrogen atom, or, X 2 However, it shows a chlorine atom, and R 5 However, it shows an ethoxy group. A hydrazone derivative or salt thereof, as shown by [the formula].

4. An agricultural and horticultural insecticide containing the hydrazone derivative or a salt thereof as an active ingredient, according to claim 3.

5. The agricultural and horticultural insecticide according to claim 4, wherein the aforementioned agricultural and horticultural insecticide is an insecticide for aphids.

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