Carbamate compound and insecticide

Abstract

To provide a carbamate compound excellent in pest controlling activity, especially insecticidal activity and / or acaricidal activity, excellent in safety, and capable of being industrially advantageously synthesized, and to provide a pest controlling agent, an insecticide or acaricide, an ectoparasite controlling agent, or an endoparasite controlling or exterminating agent containing the carbamate compound as an active ingredient.SOLUTION: A compound represented by the formula (I) or a salt thereof: [In the formula, R1 represents hydrogen atoms, substituted / unsubstituted C1 to 6 alkyl groups, or the like, R2 and R3 each independently represent hydrogen atoms or substituted / unsubstituted C1 to 6 alkyl groups, Y1 and Y2 each independently represent hydrogen atoms or groups represented by CRa, Ra represents hydrogen atoms, halogeno groups, or the like, and Q1 and Q2 each independently represent substituted / unsubstituted 5-membered heteroaryl groups, substituted / unsubstituted phenyl groups, or the like.]. (I) SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a carbamate compound and a pesticide. More specifically, the present invention relates to a carbamate compound that has excellent insecticidal and / or acaricidal activity, is highly safe, and can be synthesized industrially advantageously, as well as a pesticide, insecticide or acaricide, ectoparasite control agent, or endoparasite control or extermination agent containing the same as an active ingredient. [Background technology]

[0002] Various compounds with insecticidal and acaricidal activity have been proposed. For such compounds to be useful as pesticides, they must not only be highly effective, but also be resistant to the development of drug resistance, not cause plant damage or soil contamination, and have low toxicity to livestock and fish.

[0003] Incidentally, Patent Document 1 teaches that compounds such as those represented by formula (A) can be used to control arthropods and, in particular, insects or animal pests, including representatives of the order Acarina.

[0004] TIFF2026014715000001.tif4387

[0005] Patent Document 2 discloses a compound represented by formula (B).

[0006] TIFF2026014715000002.tif4480 [Prior art documents] [Patent documents]

[0007] [Patent Document 1] WO2022 / 157188A2 [Patent Document 2] WO2021 / 228594A1 Summary of the Invention [Problem to be solved by the invention]

[0008] An object of the present invention is to provide a carbamate compound that has excellent pest control activity, particularly excellent insecticidal and / or acaricidal activity, is safe, and can be synthesized industrially advantageously, and to provide a pest control agent, insecticide or acaricide, ectoparasite control agent, or endoparasite control or extermination agent containing the same as an active ingredient. [Means for solving the problem]

[0009] As a result of intensive research aimed at solving the above problems, the present invention has been completed, including the following aspects.

[0010] [1] A compound represented by formula (I) or a salt thereof: TIFF2026014715000003.tif3673 [In formula (I), R 1 represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylcarbonyl group, or a substituted or unsubstituted C1-6 alkoxycarbonyl group, R 2 and R 3 each independently represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group, Y 1 and Y 2 are each independently a nitrogen atom or CR a represents a group represented by R a represents a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C3-6 cycloalkyl group, and Q 1 and Q 2each independently represents a substituted or unsubstituted 5-membered heteroaryl group, a substituted or unsubstituted 6-membered heteroaryl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted fused bicyclic 10- to 12-membered heteroaryl group.

[0011] [2] A pesticide containing at least one selected from the group consisting of the compound according to [1] and a salt thereof as an active ingredient. [3] An insecticide or acaricide containing at least one selected from the group consisting of the compound according to [1] and a salt thereof as an active ingredient. [4] An ectoparasite control agent containing at least one selected from the group consisting of the compound according to [1] and a salt thereof as an active ingredient. [5] An agent for controlling or eliminating internal parasites, comprising at least one selected from the group consisting of the compound according to [1] and a salt thereof as an active ingredient. [Effects of the Invention]

[0012] The carbamate compounds of the present invention have excellent pest control activity, particularly excellent insecticidal and / or acaricidal activity, are safe, and can be synthesized industrially and advantageously. The pest control agent, insecticide or acaricide, ectoparasite control agent, or endoparasite control or extermination agent of the present invention can effectively control pests, particularly agricultural pests and mites, at low concentrations, and can also effectively control ectoparasites and endoparasites that can harm humans and livestock. DETAILED DESCRIPTION OF THE INVENTION

[0013] The carbamate compound of the present invention is a compound represented by formula (I) (hereinafter, sometimes referred to as compound (I)), or a salt of compound (I).

[0014] TIFF2026014715000004.tif3673

[0015] In the present invention, the term "unsubstituted" means that only the group that serves as the core nucleus is present. When the term "substituted" is not used and only the name of the group that serves as the core nucleus is used, it means "unsubstituted" unless otherwise specified. On the other hand, the term "substituted" means that any hydrogen atom of the core group is replaced with a group (substituent) having the same or different structure as the core group. Therefore, a "substituent" is another group bonded to the core group. There may be one or more substituents. The two or more substituents may be the same or different. Terms such as "C1-6" indicate that the core group has 1 to 6 carbon atoms. This number of carbon atoms does not include the number of carbon atoms in the substituents. For example, a butyl group having an ethoxy group as a substituent is classified as a C2 alkoxyC4 alkyl group.

[0016] The "substituent" is not particularly limited as long as it is chemically permissible and has the effect of the present invention. Examples of groups that can be the "substituent" are listed below. C1-6 alkyl groups such as methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, n-pentyl, and n-hexyl; C2-6 alkenyl groups such as vinyl, 1-propenyl, 2-propenyl (also known as allyl), 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, and 2-methyl-2-propenyl; C2-6 alkynyl groups such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, and 1-methyl-2-propynyl;

[0017] Cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group etc. C3-8 cycloalkyl groups; C6-10 aryl groups such as phenyl, tolyl, xylyl, trimethylphenyl, and naphthyl; C6-10 aryl C1-6 alkyl groups such as benzyl and phenethyl groups; 3- to 6-membered heterocyclyl groups; 3-6 membered heterocyclyl C1-6 alkyl group;

[0018] hydroxyl groups; C1-6 alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy, and t-butoxy; C2-6 alkenyloxy groups such as vinyloxy, allyloxy, propenyloxy, and butenyloxy groups; C2-6 alkynyloxy groups such as ethynyloxy groups and propargyloxy groups; C6-10 aryloxy groups such as phenoxy and naphthoxy groups; C6-10 aryl C1-6 alkoxy groups such as benzyloxy groups and phenethyloxy groups; 5- to 6-membered heteroaryloxy groups such as thiazolyloxy groups and pyridyloxy groups; 5-6-membered heteroaryl C1-6 alkyloxy groups such as thiazolylmethyloxy groups and pyridylmethyloxy groups;

[0019] Formyl group; C1-6 alkylcarbonyl groups such as acetyl and propionyl groups; formyloxy group; C1-6 alkylcarbonyloxy groups such as acetyloxy and propionyloxy groups; benzoyl group; C1-6 alkoxycarbonyl groups such as a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, an n-butoxycarbonyl group, and a t-butoxycarbonyl group; C1-6 alkoxycarbonyloxy groups such as a methoxycarbonyloxy group, an ethoxycarbonyloxy group, an n-propoxycarbonyloxy group, an i-propoxycarbonyloxy group, an n-butoxycarbonyloxy group, and a t-butoxycarbonyloxy group; carboxyl group;

[0020] halogeno groups such as fluoro, chloro, bromo, and iodo groups; C1-6 haloalkyl groups such as a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, a 3,3,3-trifluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a perfluoropropyl group, a 2,2,2-trifluoro-1-trifluoromethylethyl group, a perfluoroisopropyl group, a 1-fluoro-n-butyl group, a 4-fluorobutyl group, a 2,2,3,3,4,4,4-heptafluorobutyl group, a perfluorobutyl group, a perfluoropentyl group, a perfluorohexyl group, a chloromethyl group, a bromomethyl group, a dichloromethyl group, a dibromomethyl group, a trichloromethyl group, a tribromomethyl group, a 1-chloroethyl group, a 2,2,2-trichloroethyl group, a 1,2-dichloro-n-propyl group, a 4-chlorobutyl group, a perchlorohexyl group, and a 2,4,6-trichlorohexyl group; C2-6 haloalkenyl groups such as a 2-chloro-1-propenyl group and a 2-fluoro-1-butenyl group; C2-6 haloalkynyl groups such as a 4,4-dichloro-1-butynyl group, a 4-fluoro-1-pentynyl group, and a 5-bromo-2-pentynyl group; C1-6 haloalkoxy groups such as a trifluoromethoxy group, a 2-chloro-n-propoxy group, and a 2,3-dichlorobutoxy group; C2-6 haloalkenyloxy groups such as a 2-chloropropenyloxy group and a 3-bromobutenyloxy group; C1-6 haloalkylcarbonyl groups such as chloroacetyl, trifluoroacetyl, and trichloroacetyl groups;

[0021] amino group; C1-6 alkyl-substituted amino groups such as methylamino, dimethylamino, and diethylamino; Anilino group, naphthylamino group; C6-10 aryl C1-6 alkylamino groups such as benzylamino groups and phenethylamino groups; Formylamino group; C1-6 alkylcarbonylamino groups such as acetylamino, propanoylamino, butyrylamino, and i-propylcarbonylamino groups; C1-6 alkoxycarbonylamino groups such as a methoxycarbonylamino group, an ethoxycarbonylamino group, an n-propoxycarbonylamino group, or an i-propoxycarbonylamino group; unsubstituted or substituted aminocarbonyl groups such as aminocarbonyl, dimethylaminocarbonyl, phenylaminocarbonyl, and N-phenyl-N-methylaminocarbonyl; imino C1-6 alkyl groups such as an iminomethyl group, a (1-imino)ethyl group, and a (1-imino)-n-propyl group; substituted or unsubstituted N-hydroxyimino C1-6 alkyl groups such as an N-hydroxy-iminomethyl group, a (1-(N-hydroxy)-imino)ethyl group, a (1-(N-hydroxy)-imino)propyl group, an N-methoxy-iminomethyl group, or a (1-(N-methoxy)-imino)ethyl group; C1-6 alkoxyimino groups such as a methoxyimino group, an ethoxyimino group, an n-propoxyimino group, an i-propoxyimino group, or an n-butoxyimino group; Aminocarbonyloxy group; C1-6 alkyl-substituted aminocarbonyloxy groups such as an ethylaminocarbonyloxy group and a dimethylaminocarbonyloxy group;

[0022] mercapto group; C1-6 alkylthio groups such as a methylthio group, an ethylthio group, an n-propylthio group, an i-propylthio group, an n-butylthio group, an i-butylthio group, an s-butylthio group, and a t-butylthio group; C1-6 haloalkylthio groups such as a trifluoromethylthio group and a 2,2,2-trifluoroethylthio group; Phenylthio group, naphthylthio group; 5- to 6-membered heteroarylthio groups such as thiazolylthio groups and pyridylthio groups;

[0023] C1-6 alkylsulfinyl groups such as a methylsulfinyl group, an ethylsulfinyl group, or a t-butylsulfinyl group; C1-6 haloalkylsulfinyl groups such as a trifluoromethylsulfinyl group and a 2,2,2-trifluoroethylsulfinyl group; phenylsulfinyl group; 5- to 6-membered heteroarylsulfinyl groups such as thiazolylsulfinyl groups and pyridylsulfinyl groups;

[0024] C1-6 alkylsulfonyl groups such as methylsulfonyl, ethylsulfonyl, and t-butylsulfonyl groups; C1-6 haloalkylsulfonyl groups such as a trifluoromethylsulfonyl group and a 2,2,2-trifluoroethylsulfonyl group; phenylsulfonyl group; 5- to 6-membered heteroarylsulfonyl groups such as thiazolylsulfonyl groups and pyridylsulfonyl groups; C1-6 alkylsulfonyloxy groups such as a methylsulfonyloxy group, an ethylsulfonyloxy group, or a t-butylsulfonyloxy group; C1-6 haloalkylsulfonyloxy groups such as a trifluoromethylsulfonyloxy group and a 2,2,2-trifluoroethylsulfonyloxy group;

[0025] tri-C1-6 alkyl-substituted silyl groups such as trimethylsilyl, triethylsilyl, and t-butyldimethylsilyl; Triphenylsilyl group; cyano group; Nitro group.

[0026] Furthermore, any hydrogen atom in these "substituents" may be substituted with a group of a different structure. In this case, examples of the "substituent" include a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a halogeno group, a cyano group, and a nitro group.

[0027] The above-mentioned "3- to 6-membered heterocyclyl group" contains 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur atoms as ring-constituting atoms. Examples of the "3- to 6-membered heterocyclyl group" include 3- to 6-membered saturated heterocyclyl groups, 5- to 6-membered partially unsaturated heterocyclyl groups, and 5- to 6-membered heteroaryl groups.

[0028] Examples of the 3- to 6-membered saturated heterocyclyl group include an aziridinyl group, an epoxy group, an azetidinyl group, an oxetanyl group, a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a dioxolanyl group, and a dioxanyl group. Examples of the 5-membered partially unsaturated heterocyclyl group include a pyrrolinyl group, a dihydrofuranyl group, an imidazolinyl group, a pyrazolinyl group, an oxazolinyl group, and an isoxazolinyl group. Examples of the 6-membered partially unsaturated heterocyclyl group include a dihydropyranyl group. Examples of the 5-membered heteroaryl group include a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, and a tetrazolyl group. Examples of the 6-membered heteroaryl group include a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and a triazinyl group.

[0029] In formula (I), R 1 represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylcarbonyl group, or a substituted or unsubstituted C1-6 alkoxycarbonyl group.

[0030] R 1 The "C1-6 alkyl group" in R may be a straight chain or a branched chain. 1Examples of the "C1-6 alkyl group" in the above formula include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an s-butyl group, an i-butyl group, a t-butyl group, an n-pentyl group, an i-pentyl group, a neopentyl group, a 2-methylbutyl group, an n-hexyl group, and an i-hexyl group.

[0031] R 1 Examples of the "C3-6 cycloalkyl group" in the above formula include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.

[0032] R 1 Examples of the "C1-6 alkoxy group" in the above formula include a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an s-butoxy group, an i-butoxy group, and a t-butoxy group.

[0033] R 1 Examples of the "C1-6 alkylcarbonyl group" in the above formula include an acetyl group, a propionyl group, an n-propylcarbonyl group, an i-propylcarbonyl group, an n-butylcarbonyl group, and a t-butylcarbonyl group.

[0034] R 1 Examples of the "C1-6 alkoxycarbonyl group" in the above formula include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, an n-butoxycarbonyl group, and a t-butoxycarbonyl group.

[0035] R 1In the above, preferred substituents on the "C3-6 cycloalkyl group," "C1-6 alkoxy group," "C1-6 alkylcarbonyl group," or "C1-6 alkoxycarbonyl group" are halogeno groups such as fluoro, chloro, bromo, and iodo; hydroxyl group; C1-6 alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy, and t-butoxy; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy, 2,3-dichlorobutoxy, and trifluoromethoxy; phenyl group; "phenyl groups substituted with halogeno groups, C1-6 haloalkyl groups, or C1-6 haloalkoxy groups" such as 4-chlorophenyl, 4-trifluoromethylphenyl, and 4-trifluoromethoxyphenyl; or cyano group.

[0036] R 1 Examples of substituents on the "C1-6 alkyl group" in the formula (I) include C3-6 cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl; C2-6 alkenyl groups such as vinyl; or ethynyl; halogeno groups such as fluoro, chloro, bromo, and iodo; hydroxyl; C1-6 alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy, and t-butoxy; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy, 2,3-dichlorobutoxy, and trifluoromethoxy; C1-6 alkylthio groups such as methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, s-butylthio, and t-butylthio; phenyl; Preferred are "phenyl groups substituted with a halogeno group, a C1-6 haloalkyl group or a C1-6 haloalkoxy group", such as a 4-chlorophenyl group, a 4-trifluoromethylphenyl group or a 4-trifluoromethoxyphenyl group; or a cyano group.

[0037] In formula (I), R 2 and R 3 each independently represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group. R 2 and R 3 The "C1-6 alkyl group" in R 1 Examples of the "C1-6 alkyl group" include the same as those exemplified above.

[0038] In formula (I), Y 1 and Y 2 are each independently a nitrogen atom or CR a represents a group represented by the formula: R a represents a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C3-6 cycloalkyl group, and preferably represents a hydrogen atom or an unsubstituted C1-6 alkyl group. R a Examples of the "halogeno group" in the above formula include a fluoro group, a chloro group, a bromo group, and an iodo group. R a The "C1-6 alkyl group" in R 1 Examples of the "C1-6 alkyl group" include the same as those exemplified above. R a The "C3-6 cycloalkyl group" in R 1 Examples of the "C3-6 cycloalkyl group" include the same as those exemplified above.

[0039] In formula (I), Q 1 and Q 2 each independently represents a substituted or unsubstituted 5-membered heteroaryl group, a substituted or unsubstituted 6-membered heteroaryl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted fused bicyclic 10- to 12-membered heteroaryl group.

[0040] Q 1 and Q 2 The "5-membered heteroaryl group" in the above is a monovalent group consisting of an aromatic 5-membered ring containing one, two, or three heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur atoms as ring constituent atoms. When there are two or more heteroatoms, they may be the same or different. Examples of 5-membered heteroaryl groups include furyl groups (O1), thienyl groups (S1), isoxazolyl groups (NO1), oxazolyl groups (NO2), isothiazolyl groups (NS1), thiazolyl groups (NS2), pyrazolyl groups (NN1, NN3), imidazolyl groups (NN2), triazolyl groups (NNN1, NNN2, NNN3, NNN4, NNN5), tetrazolyl groups (NNNN1), oxadiazolyl groups (NNO1, NNO2, NNO3), and thiadiazolyl groups (NNS1, NNS2, NNS3).

[0041] TIFF2026014715000005.tif2482

[0042] TIFF2026014715000006.tif28102

[0043] TIFF2026014715000007.tif29120

[0044] TIFF2026014715000008.tif26134

[0045] In each formula, TIFF2026014715000009.tif1414 indicates the connection position, and the Markush bond indicates, for example, a furan-2-yl group or a furan-3-yl group in the case of a furanyl group (O1).

[0046] Q 1 and Q 2 The "6-membered heteroaryl group" in the above is a monovalent group consisting of an aromatic 6-membered ring containing 1, 2, 3, or 4 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur atoms as ring constituent atoms. When there are two or more heteroatoms, they may be the same or different. Examples of the 6-membered heteroaryl group include a pyridyl group (N1), a pyrazinyl group (NN4), a pyrimidinyl group (NN5), a pyridazinyl group (NN6), and a triazinyl group (NNN6).

[0047] TIFF2026014715000010.tif2695

[0048] In each formula, TIFF2026014715000011.tif1414 indicates the connection position, and the Markush bond indicates, for example, a pyridin-2-yl group, a pyridin-3-yl group, or a pyridin-4-yl group in the case of a pyridyl group (N1).

[0049] Q 1 and Q 2 The "phenyl group" in the above is a monovalent group consisting of an aromatic six-membered ring composed of six carbon atoms.

[0050] Q 1 and Q 2 The "fused bicyclic 10- to 12-membered heteroaryl group" in the above is a monovalent group consisting of an aromatic 10- to 12-membered ring formed by condensing two rings, and containing at least one heteroatom selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom as a ring-constituting atom. When there are two or more heteroatoms, they may be the same or different. Examples of fused bicyclic 10- to 12-membered heteroaryl groups include 1H,3H-furo[3,4-c]furanyl, 4,6-dihydrofuro[3,4-b]furanyl, benzoisoxazoyl (NO), indazoyl (NN, NN), quinazolinyl (NN), benzoxazoyl (NO), triazolopyridinyl (NNN), and benzothiazoyl (NS).

[0051] TIFF2026014715000012.tif36108 TIFF2026014715000013.tif2791

[0052] In each formula, TIFF2026014715000014.tif1414 indicates the connection position, and a Markush bond, for example, in the case of a benzoisoxazolyl group (NO3), indicates a 1,2-benzoxazol-3-yl group, a 1,2-benzoxazol-4-yl group, a 1,2-benzoxazol-5-yl group, a 1,2-benzoxazol-6-yl group, or a 1,2-benzoxazol-7-yl group.

[0053] Q 1 and Q 2 In the formula (I), substituents on the "5-membered heteroaryl group", "6-membered heteroaryl group", "phenyl group" or "fused bicyclic 10-12-membered heteroaryl group" include halogeno groups such as fluoro group, chloro group, bromo group and iodo group; C1-6 alkyl groups such as methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group and n-hexyl group; C1-6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group and 1-fluoro-n-butyl group; hydroxyl group; methoxy group, ethoxy group, n-propyl group Preferred are C1-6 alkoxy groups such as a 2-chloro-n-propoxy group, an i-propoxy group, an n-butoxy group, an s-butoxy group, an i-butoxy group, or a t-butoxy group; C1-6 haloalkoxy groups such as a 2-chloro-n-propoxy group, a 2,3-dichlorobutoxy group, or a trifluoromethoxy group; a phenyl group; a "phenyl group substituted with a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group" such as a 4-chlorophenyl group, a 4-trifluoromethylphenyl group, or a 4-trifluoromethoxyphenyl group; or a cyano group, with a halogeno group, a C1-6 alkyl group, a C1-6 haloalkyl group, or a cyano group being more preferred.

[0054] The salt of compound (I) is not particularly limited as long as it is an agriculturally and horticulturally acceptable salt. Examples of the salt of compound (I) include salts of inorganic acids such as hydrochloric acid and sulfuric acid; salts of organic acids such as acetic acid and lactic acid; salts of alkali metals such as lithium, sodium, and potassium; salts of alkaline earth metals such as calcium and magnesium; salts of transition metals such as iron and copper; salts of ammonia; salts of organic bases such as triethylamine, tributylamine, pyridine, and hydrazine.

[0055] The method for producing Compound (I) or a salt of Compound (I) is not particularly limited. For example, Compound (I) or a salt of Compound (I) of the present invention can be obtained by a production method utilizing a known reaction described in the Examples, etc. Furthermore, a salt of Compound (I) can be obtained from Compound (I) by a known method.

[0056] The carbamate compound of the present invention can be obtained, for example, by utilizing the chemical reaction shown below.

[0057] (Example 1) TIFF2026014715000015.tif48151

[0058] By reacting the isocyanate compound represented by formula (1) with the alcohol compound represented by formula (2), R 1 is a hydrogen atom. This reaction can be carried out in the presence of a base or a catalyst. 1 , Q 2 , R 2 , R 3 , Y 1 and Y 2 have the same meanings as those in formula (I).

[0059] (Example 2) TIFF2026014715000016.tif68151

[0060] By reacting an amine compound represented by formula (3), an alcohol compound represented by formula (2), and a carbonate compound (triphosgene) represented by formula (4), R 1 is a hydrogen atom, the compound represented by formula (I-1) can be obtained. 1 , Q 2 , R 2 , R 3 , Y 1 and Y 2 have the same meanings as those in formula (I).

[0061] (Example 3) TIFF2026014715000017.tif46157 The compound represented by formula (I-1) is reacted with an alkyl halide (RX) in the presence of NaH to obtain R 1 In this reaction, a compound represented by formula (I-2) can be obtained, in which Q is an alkyl group. 1 , Q 2 , R 2 , R 3 , Y 1 and Y 2 have the same meanings as those in formula (I), X represents a halogeno group such as a fluoro group, a chloro group, a bromo group or an iodo group, and R represents an alkyl group.

[0062] The carbamate compounds of the present invention are highly effective in controlling various agricultural pests and harmful organisms such as mites that affect plant growth. Furthermore, the carbamate compounds of the present invention are highly safe because they cause little phytotoxicity to crops and have low toxicity to fish and warm-blooded animals, and are therefore useful as active ingredients in insecticides or acaricides. Furthermore, in recent years, resistance to various existing pesticides has developed in many pests, such as diamondback moths, planthoppers, leafhoppers, and aphids, resulting in the problem of insufficient efficacy of these pesticides, and therefore pesticides that are effective against resistant pests are desired. The carbamate compounds of the present invention exhibit excellent control effects not only against susceptible pests, but also against various resistant pests and even against acaricide-resistant mites.

[0063] The carbamate compounds of the present invention are highly effective in controlling or eliminating ectoparasites and endoparasites that are harmful to humans and animals. Furthermore, they are highly safe substances due to their low toxicity to fish and warm-blooded animals. Therefore, they are useful as active ingredients in agents for controlling or eliminating ectoparasites and endoparasites.

[0064] Furthermore, the carbamate compounds of the present invention are effective against all developmental stages of organisms to be controlled, and exhibit excellent control effects against, for example, eggs, nymphs, larvae, pupae and adults of mites, insects and the like.

[0065] The pesticide of the present invention contains at least one active ingredient selected from the group consisting of compound (I) and a salt of compound (I). The amount of compound (I) or a salt of compound (I) contained in the pesticide of the present invention is not particularly limited as long as it exhibits a pest control effect. Pesticides are agents for controlling pests, and include insecticides or acaricides, ectoparasite control agents, and endoparasite control or extermination agents.

[0066] [Insecticidal or acaricide] The insecticide or acaricide of the present invention contains at least one active ingredient selected from the group consisting of compound (I) and a salt of compound (I). The amount of compound (I) and a salt of compound (I) contained in the insecticide or acaricide of the present invention is not particularly limited as long as it exhibits an insecticidal or acaricidal effect.

[0067] The pest control agent, or insecticide or acaricide of the present invention is preferably used on plants such as grains; vegetables; root vegetables; potatoes; flowers; fruit trees; ornamental plants, trees such as tea, coffee, and cacao; pasture grass; turf; and cotton. When applied to plants, the pesticide, insecticide or acaricide of the present invention may be applied to any part of the plant, such as leaves, stems, stalks, flowers, buds, fruits, seeds, sprouts, roots, tubers, tuberous roots, shoots, cuttings, etc. Furthermore, the pesticide, insecticide, or acaricide of the present invention is not particularly limited by the species of plant to which it is applied, and examples of plant species include original species, varieties, improved varieties, cultivated varieties, mutants, hybrids, and genetically modified organisms (GMOs).

[0068] The pesticide of the present invention can be used for seed treatment, foliage application, soil application, water surface application, etc. to control various agricultural pests and mites.

[0069] Specific examples of various agricultural pests and mites that can be controlled by the pest control agent of the present invention are shown below.

[0070] (1) a butterfly or moth of the order Lepidoptera (a) Arctiidae moths, such as Hyphantria cunea and Lemyra imparilis; (b) Moths of the Bucculatricidae family, e.g., Bucculatrix pyrivorella; (c) Moths of the family Carposinidae, e.g., the peach fruit moth (Carposina sasakii); (d) Crambidae moths, for example, Diaphania spp., such as Diaphania indica and Diaphania nitidalis; for example, Ostrinia spp., such as Ostrinia furnacalis, Ostrinia nubilalis, and Ostrinia scapulalis; and others, such as Chilo suppressalis, Cnaphalocrocis medinalis, Conogethes punctiferalis, Diatraea grandiosella, Glyphodes pyloalis, and Hellula undalis), Parapediasia teterrella; (e) Moths of the family Gelechiidae, such as the potato leaf moth (Helcystogramma triannulella), the red bollworm (Pectinophora gossypiella), the potato leaf moth (Phthorimaea operculella), and the potato moth (Sitotroga cerealella); (f) Moths of the Geometridae family, for example, Ascotis selenaria; (g) Moths of the Gracilariidae family, such as Caloptilia theivora, Phyllocnistis citrella, and Phyllonorycter ringoniella; (h) butterflies of the Hesperiidae family, e.g., Parnara guttata; (i) Lasiocampidae moths, for example, Malacosoma neustria; (j) Lymantriidae moths, for example, Lymantria spp., Lymantria dispar, Lymantria monacha; and others, such as Euproctis pseudoconspersa, Orgyia thyellina;

[0071] (k) Lyonetiidae moths, for example, Lyonetia spp., such as the peach leafminer (Lyonetia clerkella) and the silver leafminer (Lyonetia prunifoliella malinella); (l) Noctuidae moths, for example, Spodoptera spp., such as Spodoptera depravata, Spodoptera eridania, Spodoptera exigua, Spodoptera frugiperda, Spodoptera littoralis, and Spodoptera litura; for example, Autographa spp., such as Autographa gamma and Autographa nigrisigna; for example, Agrotis spp., such as Agrotis ipsilon and Agrotis nigrisigna. segetum; for example, Helicoverpa spp., such as Helicoverpa armigera, Helicoverpa assulta, and Helicoverpa zea; for example, Heliothis spp., such as Heliothis armigera and Heliothis virescens; and others, such as Aedia leucomelas, Ctenoplusia agnata, Eudocima tyrannus, Mamestra brassicae, Mythimna separata, Naranga aenescens, Panolis japonica, and Peridroma saucia), soybean looper (Pseudoplusia includens), nettle looper (Trichoplusia ni); (m) Moths of the Nolidae family, e.g., Earias insulana; (n) Butterflies of the family Pieridae, such as Pieris spp., Pieris brassicae, Pieris rapae crucivora; (o) Moths of the Plutellidae family, for example, Acrolepiopsis spp., such as the onion moth (Acrolepiopsis sapporensis) and the Japanese potato moth (Acrolepiopsis suzukiella); and others, such as the diamondback moth (Plutella xylostella); (p) Moths of the Pyralidae family, such as Cadra cautella, Elasmopalpus lignosellus, Etiella zinckenella, and Galleria mellonella; (q) Moths of the family Sphingidae, e.g., Manduca spp., tomato hornworm (Manduca quinquemaculata), tobacco hornworm (Manduca sexta);

[0072] (r) Moths of the Stathmopodidae family, for example, the persimmon pulp moth ( Stathmopoda masinissa ); (s) Moths of the Tineidae family, e.g., Tinea translucens; (t) Tortricidae moths, for example, Adoxophyes spp., such as the smaller tea tortrix moth (Adoxophyes honmai) and the smaller apple tortrix moth (Adoxophyes orana); Archips spp., such as the apple tortrix moth (Archips breviplicanus) and the green leaf tortrix moth (Archips fuscocupreanus); and other moths, such as the spruce budworm moth (Choristoneura fumiferana), the codling moth (Cydia pomonella), the grapevine moth (Eupoecilia ambiguella), the pear fruit moth (Grapholitha molesta), the tea tortrix moth (Homona magnanima), the bean fruit moth (Leguminivora glycinivorella), and the bean leaf moth (Lobesia botrana), bean pea moth (Matsumuraeses phaseoli), springtail moth (Pandemis heparana), Japanese bush moth (Sparganothis pilleriana); (u) Moths of the Yponomeutidae family, such as the apple fruit moth (Argyresthia conjugella).

[0073] (2) Thysanoptera pests (a) Phlaeothripidae, e.g., Ponticulothrips diospyrosi; (b) From the family Thripidae, for example, from the genus Frankliniella, such as Frankliniella intonsa and Frankliniella occidentalis; from the genus Thrips, for example, Thrips palmi and Thrips tabaci; and others, such as Heliothrips haemorrhoidalis and Scirtothrips dorsalis.

[0074] (3) Hemiptera pests (A)Archaeorrhyncha (a) Delphacidae, for example, Laodelphax striatella, Nilaparvata lugens, Perkinsiella saccharicida, and Sogatella furcifera.

[0075] (B)Clypeorrhyncha (a) Cicadellidae, for example, Empoasca spp., such as potato leafhopper (Empoasca fabae), persimmon leafhopper (Empoasca nipponica), tea green leafhopper (Empoasca onukii), bean green leafhopper (Empoasca sakaii); and others, such as Arboridia apicalis, green long leafhopper (Balclutha saltuella), giant leafhopper (Epiacanthus stramineus), small leafhopper (Macrosteles striifrons), green rice leafhopper (Nephotettix cinctinceps).

[0076] (C) Heteroptera (a) Alydidae, e.g., Riptortus clavatus; (b) Coreidae, e.g., Cletus punctiger, Leptocorisa chinensis; (c) Lygaeidae, such as Blissus leucopterus, Cavelerius saccharivorus, and Togo hemipterus; (d) Miridae, such as the black-spotted rice bug (Halticus insularis), the rusty rice bug (Lygus lineolaris), the cotton freehopper (Psuedatomoscelis seriatus), the long-gray rice bug (Stenodema sibiricum), the red-striped rice bug (Stenotus rubrovittatus), and the rice beetle (Trigonotylus caelestialium);

[0077] (e) Pentatomidae, for example, Nezara spp., such as Nezara antennata and Nezara viridula; Eysarcoris spp., such as Eysarcoris aeneus, Eysarcoris lewisi, Eysarcoris ventralis, and other species of the genus Dolycoris, including Dolycoris baccarum, Eurydema rugosum, Glaucias subpunctatus, and Halyomorpha halys), striped stink bug (Piezodorus hybneri), brown-winged green bug (Plautia crossota), black rice bug (Scotinophora lurida); (f) Pyrrhocoridae, e.g., Dysdercus cingulatus; (g) Rhopalidae, e.g., Rhopalus msculatus; (h) Scutelleridae, e.g., Eurygaster integriceps; (i) Tingidae, for example, Stephanitis nashi.

[0078] (D) Sternorrhyncha (a) Adelgidae, e.g., Adelges laricis; (b) Aleyrodidae, such as Bemisia spp., including the silverleaf whitefly (Bemisia argentifolii) and the tobacco whitefly (Bemisia tabaci); and others, including the citrus spiny whitefly (Aleurocanthus spiniferus), the citrus whitefly (Dialeurodes citri), and the greenhouse whitefly (Trialeurodes vaporariorum). (c) Aphididae, for example, Aphis spp., such as the bean aphid Aphis craccivora, the black bean aphid Aphis fabae, the strawberry aphid Aphis forbesi, the cotton aphid Aphis gossypii, the European apple aphid Aphis pomi, the elderberry aphid Aphis sambuci, and the willow aphid Aphis spiraecola; for example, Rhopalosiphum spp., such as the corn aphid Rhopalosiphum maidis and the wheat aphid Rhopalosiphum padi; for example, Dysaphis spp., such as the plantain aphid Dysaphis plantaginea, Dysaphis radicola; for example, Macrosiphum spp., wheat aphids (Macrosiphum avenae), tulip aphids (Macrosiphum euphorbiae); for example, Myzus spp.) of the Japanese plum aphid (Myzus cerasi), green peach aphid (Myzus persicae), and Japanese burdock aphid (Myzus varians); and other insects such as the pea aphid (Acyrthosiphon pisum), potato aphid (Aulacorthum solani), strawberry aphid (Brachycaudus helichrysi), radish aphid (Brevicoryne brassicae), strawberry woolly aphid (Chaetosiphon fragaefolii), peach butterbur aphid (Hyalopterus pruni), lettuce aphid (Hyperomyzus lactucae), false radish aphid (Lipaphis erysimi), and broad bean aphid (Megoura viciae), wheat aphid (Metopolophium dirhodum), lettuce aphid (Nasonovia ribis-nigri), hop wart aphid (Phorodon humuli), wheat green aphid (Schizaphis graminum), wheat long-horn aphid (Sitobion avenae), and phyllocanth aphid (Toxoptera aurantii);.

[0079] (d) from the family Coccidae, for example, Ceroplastes spp., Ceroplastes ceriferus, Ceroplastes rubens; (e) Diaspididae, Pseudaulacaspis spp., such as Pseudaulacaspis pentagona and Pseudaulacaspis prunicola; Unaspis spp., such as Unaspis euonymi and Unaspis yanonensis; and others, such as Aonidiella aurantii, Comstockaspis perniciosa, Fiorinia theae, and Pseudaonidia paeoniae. (f) Margarodidae, e.g., Drosicha corpulenta, Icerya purchasi; (g) Phylloxeridae, e.g., the grape aphid (Viteus vitifolii); (h) Pseudococcidae, for example, Planococcus spp., such as Planococcus citri, Planococcus kuraunhiae; and others, such as Phenacoccus solani, Pseudococcus comstocki; (i) From the family Psyllidae, for example, from the genus Psylla, such as the apple psylla (Psylla mali) and the pear psylla (Psylla pyrisuga); and others, such as the citrus psylla (Diaphorina citri).

[0080] (4) Pests of the Polyphaga beetle suborder (a) Anobiidae, e.g., the cigarette beetle (Lasioderma serricorne); (b) Attelabidae, e.g., Byctiscus betulae, Rhynchites heros; (c) Bostrichidae, e.g., Lyctus brunneus; (d) Brentidae, e.g., sweet potato weevil (Cylas formicarius); (e) Buprestidae, e.g., the red-spotted jewel beetle (Agrilus sinuatus); (f) Cerambycidae, for example, Anoplophora malasiaca, Monochamus alternatus, Psacothea hilaris, and Xylotrechus pyrrhoderus; (g) from the family Chrysomelidae, for example, from the genus Bruchus, the pea weevil (Bruchus pisorum) and the broad bean weevil (Bruchus rufimanus); from the genus Diabrotica, for example, the northern corn rootworm (Diabrotica barberi), the southern corn rootworm (Diabrotica undecimpunctata), and the western corn rootworm (Diabrotica virgifera); from the genus Phyllotreta, for example, the flea beetle (Phyllotreta nemorum) and the striped flea beetle (Phyllotreta striolata); and others, such as the cucumber beetle (Aulacophora femoralis), the adzuki bean weevil (Callosobruchus chinensis), and the turtle beetle (Cassida nebulosa), Tensite leaf beetle (Chaetocnema concinna), Colorado potato beetle (Leptinotarsa ​​decemlineata), Rice leaf beetle (Oulema oryzae), Eggplant long-striped leaf beetle (Psylliodes angusticollis);

[0081] (h) Coccinellidae, for example, Epilachna spp., Epilachna varivestis, Epilachna vigintioctopunctata; (i) From the family Curculionidae, for example, from the genus Anthonomus, the boll weevil (Anthonomus grandis) and the pear weevil (Anthonomus pomorum); from the genus Sitophilus, for example, the granary weevil (Sitophilus granarius) and the maize weevil (Sitophilus zeamais); and other insects, such as the rice weevil (Echinocnemus squameus), the potato weevil (Euscepes postfasciatus), the pine weevil (Hylobius abietis), the alfalfa weevil (Hypera postica), the rice water weevil (Lissohoptrus oryzophilus), and the vine weevil (Otiorhynchus sulcatus), red-legged weevil (Sitona lineatus), grass weevil (Sphenophorus venatus); (j) Elateridae, for example, Melanotus spp., such as the yellow-striped click beetle (Melanotus fortnumi) and the yellow-striped click beetle (Melanotus tamsuyensis); (k) Nitidulidae, e.g., Epuraea domina; (l) Scarabaeidae, for example, Anomala spp., such as Anomala cuprea and Anomala rufocuprea; other beetles such as Cetonia aurata, Gametis jucunda, Heptophylla picea, Melolontha melolontha, and Popillia japonica; (m) of the Scolytidae family, e.g., Ips typographus; (n) Staphylinidae, e.g., Paederus fuscipes; (o) Tenebrionidae, e.g., Tenebrio molitor, Tribolium castaneum; (p) Of the Trogossitidae family, for example, the red widow (Tenebroides mauritanicus).

[0082] (5) Diptera pests (A) Flies (Brachycera) (a) Agromyzidae, for example, Liriomyza spp., such as Liriomyza bryoniae, Liriomyza chinensis, Liriomyza sativae, and Liriomyza trifolii; and others, such as Chromatomyia horticola and Agromyza oryzae. (b) Anthomyiidae, e.g., Delia spp., seed flies (Delia platura), cabbage flies (Delia radicum); and others, such as the beet root fly (Pegomya cunicularia). (c) Drosophilidae, e.g., Drosophila spp., Drosophila melanogaster, Drosophila suzukii; (d) Ephydridae, e.g., Hydrellia griseola; (e) of the family Psilidae, e.g., the carrot rust fly (Psila rosae); (f) From the family Tephritidae, for example, from the genus Bactrocera, for example, the melon fly (Bactrocera cucurbitae) and the oriental fruit fly (Bactrocera dorsalis); from the genus Rhagoletis, for example, the European cherry fruit fly (Rhagoletis cerasi) and the apple fruit fly (Rhagoletis pomonella); and others, for example, the Mediterranean fruit fly (Ceratitis capitata) and the olive fruit fly (Dacus oleae).

[0083] (B) Nematocera (a) Cecidomyiidae, for example, soybean pod gall midge (Asphondylia yushimai), sorghum gall midge (Contarinia sorghicola), Hessian fly (Mayetiola destructor), and wheat gall midge (Sitodiplosis mosellana).

[0084] (6) Orthoptera pests (a) From the grasshopper family (Acrididae), for example, from the genus Schistocerca, the American locust (Schistocerca americana) and the desert locust (Schistocerca gregaria); and others, such as the Australian bush locust (Chortoicetes terminifera), the Moroccan locust (Dociostaurus maroccanus), the migratory locust (Locusta migratoria), the brown locust (Locustana pardalina), the red bush locust (Nomadacris septemfasciata), and the oriental grasshopper (Oxya yezoensis); (b) Gryllidae, e.g., the European house cricket (Acheta domestica), the field cricket (Teleogryllus emma); (c) of the family Gryllotalpidae, e.g., the mole cricket (Gryllotalpa orientalis); (d) From the family Tettigoniidae, for example, the grasshopper (Tachycines asynamorus).

[0085] (7) Mites (Acari) (A) Acaridida mites of the order Astigmata (a) Mites of the family Acaridae, for example, Rhizoglyphus spp., such as Rhizoglyphus echinopus and Rhizoglyphus robini; for example, Tyrophagus spp., such as Tyrophagus neiswanderi, Tyrophagus perniciosus, Tyrophagus putrescentiae, and Tyrophagus similis; and others, such as Acarus siro, Aleuroglyphus ovatus, and Mycetoglyphus fungivorus.

[0086] (B) Prostigmata (Actinedida) (a) Mites of the family Tetranychidae, for example, Bryobia spp., such as clover spider mites (Bryobia praetiosa) and false clover spider mites (Bryobia rubrioculus); for example, Eotetranychus spp., such as Eotetranychus asiaticus, Eotetranychus boreus, Eotetranychus celtis, Eotetranychus geniculatus, Eotetranychus kankitus, Eotetranychus pruni, Eotetranychus shii, Eotetranychus smithi, Eotetranychus spp. suginamensis, Eotetranychus uncatus; for example, of the genus Oligonychus, such as Oligonychus hondoensis, Oligonychus ilicis, Oligonychus karamatus, Oligonychus mangiferus, Oligonychus orthius, Oligonychus perseae, Oligonychus pustulosus, Oligonychus shinkajii, Oligonychus ununguis; for example, of the genus Panonychus, such as Panonychus citri), Panonychus mori, Panonychus ulmi; e.g., Tetranychus spp.) such as Tetranychus cinnabarinus, Tetranychus evansi, Tetranychus kanzawai, Tetranychus ludeni, Tetranychus quercivorus, Tetranychus phaselus, Tetranychus urticae, Tetranychus viennensis; Aponychus spp., for example, Aponychus corpuzae, Aponychus firmianae; Sasanychus spp., for example, Sasanychus akitanus, Sasanychus pusillus; for example, Shizotetranychus spp., such as Shizotetranychus celarius, Shizotetranychus longus, Shizotetranychus miscanthi, Shizotetranychus recki, and Shizotetranychus schizopus; and others, such as Tetranychina harti, Tuckerella pavoniformis, and Yezonychus sapporensis.

[0087] (b) Mites of the Tenuipalpidae family, for example, Brevipalpus spp., such as the grape spider mite (Brevipalpus lewisi), the tea spider mite (Brevipalpus obovatus), the southern spider mite (Brevipalpus phoenicis), the cactus spider mite (Brevipalpus russulus), and the greenhouse spider mite (Brevipalpus californicus); for example, Tenuipalpus spp., such as the orchid spider mite (Tenuipalpus pacificus) and the oyster spider mite (Tenuipalpus zhizhilashviliae); and others, such as the pineapple spider mite (Dolichotetranychus floridanus). (c) Mites of the family Eriophyidae, for example, Aceria spp., such as Aceria diospyri, Aceria ficus, Aceria japonica, Aceria kuko, Aceria paradianthi, Aceria tiyingi, Aceria tulipae, and Aceria zoysiea; for example, Eriophyes spp., such as Eriophyes chibaensis and Eriophyes emarginatae; for example, Aculops spp., such as Aculops tomato. lycopersici, citrus rust mite (Aculops pelekassi); for example, Aculus spp., peach rust mite (Aculus fockeui), apple rust mite (Aculus schlechtendali); others, such as the tea long rust mite (Acaphylla theavagrans), tea rust mite (Calacarus carinatus), grape leafminer mite (Colomerus vitis), grape rust mite (Calepitrimerus vitis), pear rust mite (Epitrimerus pyri), sweetmeat rust mite (Paraphytoptus kikus), peach rust mite (Paracalacarus podocarpi), and Ryukyu citrus rust mite (Phyllocotruta citri); (d) Mites of the family Transonemidae, for example, Tarsonemus spp., such as Tarsonemus bilobatus and Tarsonemus waitei; others, such as Phytonemus pallidus and Polyphagotarsonemus latus; (e) Mites of the family Penthaleidae, for example, Penthaleus spp., such as Penthaleus erythrocephalus and Penthaleus major.

[0088] The pest control agent of the present invention may be mixed or used in combination with other active ingredients such as fungicides, insecticides / acaricides, nematicides, and soil pesticides; plant regulators, synergists, fertilizers, soil conditioners, and animal feed. A combination of the pesticide of the present invention and another active ingredient is expected to produce a synergistic effect in terms of insecticidal, acaricidal, and nematicidal activity. The synergistic effect can be confirmed by Colby's formula (Colby, SR; Calculating Synergistic and Antagonistic Responses of Herbicide Combinations; Weeds 15, pp. 20-22, 1967) in accordance with a standard method.

[0089] Specific examples of insecticides, miticides, nematicides, soil pesticides, anthelmintics and the like that can be mixed or used in combination with the pest control agent of the present invention are shown below.

[0090] (1) Acetylcholinesterase inhibitors: (a) Carbamates: alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, oxamyl, pirimicarb, propoxal, thiodicarb, thiofanox, triazamate, trimethacarb, XMC, xylylcarb, fenothiocarb, MIPC, MPMC, MTMC, aldoxycarb, alixycarb, aminocarb, bufencarb, cloethocarb, metam sodium, promecarb;

[0091] (b) Organophosphates: Acephate, Azamethiphos, Azinphos-ethyl, Azinphos-methyl, Cadusafos, Chlorethoxyphos, Chlorfenvinphos, Chlormephos, Chlorpyrifos, Chlorpyrifos-methyl, Coumaphos, Cyanophos, Demeton-S-methyl, Diazinon, Dichlorvos / DDVP, Dicrotophos, Dimethoate, Dimethylvinphos, Disulfoton, EPN, Ethion, Ethoprophos, Famfur, Fenamiphos, Fenitrothion, Fenthion, Fosthiazate, Heptenophos, Imicyaphos, Isofenphos, Isocarbophos, Isoxathion, Malathion, Mecarbam, Methamidophos, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion, Parathion-methyl, Fe thionate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirinphos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, vamidothion, bromophos-ethyl, BRP, carbophenothion, cyanofenphos, demeton-S-methylsulfone, dialifos, diclofenthion, dioxabenzophos, etrimphos, fensulfothion, flupyrazophos, fonofos, formothion, fosmetilan, isazophos, iodofenphos, methacrifos, pirimiphos-ethyl, phosphocarb, propafos, protoate, sulprofos.

[0092] (2) GABA-gated chloride channel antagonists: acetoprole, chlordane, endosulfan, ethiprole, fipronil, pyrafluprole, pyriprole, camphechlor, heptachlor, and dienochlor. (3) Sodium channel modulators: acrinathrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cyclopentyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(1R)-trans isomer], deltamethrin, empenthrin [(EZ)-(1R)-isomer], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, and flumetrin. tau-fluvalinate, halfenprox, imiprothrin, kadesrin, permethrin, phenothrin [(1R)-trans isomer], prallethrin, pyrethrum, resmethrin, silafluofen, tefluthrin, tetramethrin [(1R)-isomer], tralomethrin, transfluthrin, allethrin, pyrethrin, pyrethrin I, pyrethrin II, profluthrin, dimefluthrin, bioethanomethrin, biopermethrin, transpermethrin, fenfluthrin, fenpyrithrin, flubrocythrinate, flufenprox, metofluthrin, protrifenbut, pyresmethrin, terallethrin.

[0093] (4) Nicotinic acetylcholine receptor agonists: acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam, sulfoxaflor, nicotine, flupyradifurone, and flupirimine. (5) Nicotinic acetylcholine receptor allosteric modulators: spinetoram, spinosad. (6) Chloride channel activators: abamectin, emamectin benzoate, lepimectin, milbemectin, ivermectin, selamectin, doramectin, eprinomectin, moxidectin, milbemycin, milbemycin oxime, nemadectin. (7) Juvenile hormone-like substances: hydroprene, kinoprene, methoprene, fenoxycarb, pyriproxyfen, diofenolan, epofenonane, triprene. (8) Other nonspecific inhibitors: methyl bromide, chloropicrin, sulfuryl fluoride, borax, and tartar emetic. (9) Homoptera-selective antifeedants: flonicamid, pymetrozine, pyrifluquinazone.

[0094] (10) Acarid growth inhibitors: clofentezine, diflavidazine, hexythiazox, etoxazole. (11) Microbial-derived insect midgut membrane disruptors: Bacillus thuringiensis subsp. israelensi, Bacillus sphaericus, Bacillus thuringiensis subsp. aizawai, Bacillus thuringiensis subsp. kurstaki, Bacillus thuringiensis subsp. tenebrionis, Bt crop proteins, Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / Cry35Ab1. (12) Mitochondrial ATP biosynthesis enzyme inhibitors: diafenthiuron, azocyclotin, cyhexatin, fenbutatin oxide, propargite, and tetradifon. (13) Oxidative phosphorylation uncouplers: chlorfenapyr, sulfluramide, DNOC, binapacryl, dinobuton, and dinocap. (14) Nicotinic acetylcholine receptor channel blockers: bensultap, cartap hydrochloride, nereistoxin, thiosultap-sodium salt, thiocyclam. (15) Chitin synthesis inhibitors: bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, buprofezin, and fluazuron. (16) Dipteran molting disruptor: cyromazine. (17) Molting hormone receptor agonists: chromafenozide, halofenozide, methoxyfenozide, tebufenozide. (18) Octopamine receptor agonists: amitraz, demiditraz, chlordimeform. (19) Mitochondrial electron transport chain complex III inhibitors: acequinocyl, fluacrypyrim, hydramethylnon, bifenazate. (20) Mitochondrial electron transport chain complex I inhibitors: fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad, and rotenone.

[0095] (21) Voltage-gated sodium channel blockers: indoxacarb, metaflumizone. (22) Acetyl-CoA carboxylase inhibitors: spirodiclofen, spiromesifen, spirotetramat, spiropydione. (23) Mitochondrial electron transport chain complex IV inhibitors: aluminum phosphide, calcium phosphide, phosphine, zinc phosphide, cyanide. (24) Mitochondrial electron transport chain complex II inhibitors: cyenopyrafen, cyflumetofen, and piflubumid. (25) Ryanodine receptor modulators: chlorantraniliprole, cyantraniliprole, flubendiamide, cyclaniliprole, tetraniliprole. (26) Mixed function oxidase inhibitor compound: piperonyl butoxide. (27) Latrophilin receptor agonists: depsipeptides, cyclic depsipeptides, 24-membered cyclic depsipeptides, emodepsides. (28) Other agents (mechanism of action unknown): acinonapyr, azadirachtin, benzoximate, bromopropylate, chinomethionate, cryolite, dicofol, pyridalyl, benclothiaz, sulfur, amidoflumet, 1,3-dichloropropene, DCIP, phenisobromorate, benzomate, metaldehyde, chlorbenzilate, clothiazoben, dicyclanil, fenoxacrim, fentrifanil, flubenzimine, fluphenazine, gossiplura, japonirua, methoxadiazone, petroleum, sodium oleate, tetrasulfur, triarane, afidopyropen, furometo Quinone, flufiprol, fluensulfone, meperfluthrin, tetramethylfluthrin, tralopyril, methylneodecanamide, fluralaner, afoxolaner, fluxametamide, 5-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-(1H-1,2,4-triazol-1-yl)benzonitrile (CAS: 943137-49-3), broflanilide, triflumezopyrim, dichloromezothiazol, oxazosulfil, other metadiamides, cyclopyrazoflurane.

[0096] (29) Anthelmintics: (a) Benzimidazoles: fenbendazole, albendazole, triclabendazole, oxibendazole, mebendazole, oxfendazole, perbendazole, flubendazole, febantel, netobimin, thiophanate, thiabendazole, and cambindazole; (b) Salicylanilides: closantel, oxyclozanide, rafoxanide, niclosamide; (c) Substituted phenols: nitroxynil, nitroscate; (d) Pyrimidines: pyrantel, morantel; (e) Imidazothiazoles: levamisole, tetramisole; (f) Tetrahydropyrimidines: praziquantel, epsiprantel; (g) Other anthelmintics: Cyclodien, Rhiania, clorsulon, metronidazole, demiditraz, piperazine, diethylcarbamazine, dichlorophen, monepantel, tribendimidine, amidantel, thiacetarsamide, melarsomine, arsenamide.

[0097] Specific examples of fungicides that can be mixed or used in combination with the pest control agent of the present invention are shown below. (A) Nucleic acid synthesis metabolic inhibitor (1) RNA polymerase I inhibitors Benalaxyl, Benalaxyl M, Furalaxyl, Metalaxyl, Metalaxyl M; Oxadixyl; Ofurace. (2) Adenosine deaminase inhibitors Bupirimate, dimethirimol, etirimol. (3) DNA / RNA biosynthesis inhibitors Hymexazole, octilinone. (4) DNA topoisomerase type II inhibitors Oxolinic acid.

[0098] (B) Inhibitors of cytoskeleton and motor proteins (1) β-tubulin polymerization inhibitor Benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate, thiophanate methyl, diethofencarb, zoxamide, Ethaboxam. (2) Other inhibitors Pencycuron, Fluopicolide, Fenamacryl, Metrafenone, Pyriophenone.

[0099] (C) Respiratory inhibitors (1) Complex I: Inhibitor of NADH oxidoreductase Diflumetrim, tolfenpyrad, fenazaquin. (2) Complex II: Inhibitors of succinate dehydrogenase Benodani, flutolanil, mepronil; isofetamide; fluopyram; fenfuram; carboxin, oxycarboxin; thifluzamide; benzovindiflupyr, bixafen, fluindapyr, fluxapyroxad, furametpyr, inpirfluxam, isopyrazam, penflufen, penthiopyrad, sedaxane; isoflucipram; pydiflumetofen; boscalid; pyraziflumid. (3) Complex III: Inhibitor of the Qo site (cyt b gene) of cytochrome bc1 (ubiquinol oxidase) Azoxystrobin, cumoxystrobin, enoxastrobin, flufenoxystrobin, picoxystrobin, pyraoxystrobin; mandestrobin; pyraclostrobin, pyrametostrobin, triclopyricarb; kresoxim-methyl, trifloxystrobin; dimoxystrobin, phenaminestrobin, metominostrobin, orysastrobin; famoxadone; fluoxastrobin; fenamidone; pyribencarb. (4) Complex III: Inhibitors of the Qi site of ubiquinone reductase Cyazofamid; Amisulbrom; Fenpicoxamid. (5) Uncouplers of oxidative phosphorylation Binapacryl, dinocap, meptyl dinocap; fluazinam. (6) Inhibitors of oxidative phosphorylation and ATP synthase Triphenyltin acetate, triphenyltin chloride, triphenyltin hydroxide. (7) ATP transport inhibitors Silthiofam. (8) Complex III: Inhibitors of ubiquinone reductase (Qo site, stigmatellin-binding subsite) Ametoctrazine.

[0100] (D) Amino acid and protein synthesis inhibitors Cyprodinil, mepanipyrim, pyrimethanil, blasticidin S, kasugamycin, kasugamycin hydrochloride, streptomycin, oxytetracycline.

[0101] (E) Signal transduction inhibitors Quinoxyfen, proquinazid, fenpiclonil, fludioxonil, chlozolinate, dimethaclon, iprodione, procymidone, vinclozolin.

[0102] (F) Agents that inhibit lipid biosynthesis or transport / cell membrane structure or function Edifenphos, iprobenfos, pyrazophos; isoprothiolane. Biphenyl, chloroneb, dicloran, quintozene, tecnazene, tolclofos-methyl; etridiazole; iodocarb, propamocarb, propamocarb hydrochloride, prothiocarb; natamycin; oxathiapiproline.

[0103] (G) Inhibitors of sterol biosynthesis in cell membranes (1) Inhibitor of C14 demethylase (erg11 / cyp51) in sterol biosynthesis Triforine; pyrifenox, pyrisoxazole; fenarimol, nuarimol; imazalil, oxpoconazole, pefurazoate, prochloraz, triflumizole; azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, prothioconazole. (2) Inhibitors of Δ14 reductase and Δ8→Δ7-isomerase (erg24, erg2) in sterol biosynthesis Aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph; fenpropidin, piperaline; spiroxamine. (3) Inhibitors of 3-ketoreductase (erg27) in the C4 demethylation of sterol biosynthesis Fenhexamid, fenpyrazamine. (4) Inhibitors of squalene epoxidase (erg1) in the sterol biosynthesis pathway Piributicarb, naftifine, terbinafine.

[0104] (H) Inhibitors of cell wall biosynthesis Polyoxins. Dimethomorph, flumorph, pyrimorph; benthiavalicarb, iprovalicarb, valifenalate; mandipropamide.

[0105] (I) Inhibitor of cell wall melanin synthesis Fthalide, pyroquilon, tricyclazole, carpropamid, diclocymet, fenoxanil, tolprocarb.

[0106] (P) Resistance inducer in host plants Acibenzolar-S-methyl; probenazole; tiadinil, isotianil. Laminarin. Japanese knotweed extract. Bacillus mycoides isolate J. Fosetyl, phosphorous acid and salt, fosetyl calcium, fosetyl sodium.

[0107] (U) Agents with unknown mechanism of action Cymoxanil; tecloftalam; triazoxide; flusulfamide; diclomedine; cyflufenamid; dodine, dodine free base; fluthianil; ferimzone; tebufloquine; picarbutrazox; validamycin. Fluoxapyrroline, florylpicoxamide, fluopimomide, ipflufenoquin, methyltetraprole, pyridaclomethyl, pyrapropoin, aminopyrifen, diclobenthiazox, ipfentrifluconazole, mefentrifluconazole, quinofumelin, dipimethitron.

[0108] (M) Agents exhibiting multisite contact activity Copper (various salts), basic copper sulfate, Bordeaux mixture, copper hydroxide, copper naphthalate, copper oxychloride, copper sulfate, copper oxide, copper oxine; sulfur, lime sulfur; ferbam, mancozeb, maneb, metiram, propineb, thiuram, zinc thiazole, zineb, ziram; captan, captafol, folpet; chlorothalonil; dichlofluanid, tolylfluanid; guazatine, guazatine acetate, iminoctadine, iminoctadine acetate, iminoctadine albesilate; anilazine; dithianone; chinomethionate; fluorimide; metasulfocarb.

[0109] (N) Other agents: DBEDC, fluorofolpet, guazatine acetate, bis(8-quinolinolato)copper(II), propamidine, chloropicrin, cyprofuram, Agrobacterium, bethoxadin, diphenylamine, methylisothianate (MITC), mildeomycin, capsaicin, khufuraneb, cyprosulfamide, dazomet, debacarb, dichlorophen, difenzoquat, difenzoquat methylsulfonate, flumetober, fosetyl calcium, fosetyl sodium, irumamycin, na Isopropyl myristate, nitroisopropyl myristate, oxamocarb, propamocin sodium, pyrrolnitrin, tebufloquine, tolnifanide, zaliramide, algophase, amicarthiazol, oxathiapiprolin, metiram zinc, benzazole, triclamide, uniconazole, mildeomycin, oxyfenthiin, picarbutrazox.

[0110] Specific examples of plant regulators that can be mixed or used in combination with the pest control agent of the present invention are shown below. 1-methylcyclopropene, 2,3,5-triiodobenzoic acid, IAA, IBA, MCPA, MCPB, 4-CPA, 5-aminolevulinic acid hydrochloride, 6-benzylaminopurine, abscisic acid, aviglycine hydrochloride, ancymidol, butruarin, calcium carbonate, calcium chloride, calcium formate, calcium peroxide, lime sulfur, calcium sulfate, chlormequat chloride, chlorpropham, choline chloride, cloprop, cyanamide, cyclanilide, daminozide, decyl alcohol, dichlorprop, dikegulac, dimethipine, diquat, ethephon, ethychlozate, flume Traline, flurprimidol, forchlorfenuron, gibberellin A, gibberellin A3, hymexazole, inabenfide, isoprothiolane, kinetin, maleic hydrazide, mefluidide, mepiquat chloride, oxidized glutathione, paclobutrazol, pendimethalin, prohexadione calcium, prohydrojasmone, pyraflufen-ethyl, synthofen, sodium 1-naphthaleneacetate, sodium cyanate, streptomycin, thidiazuron, triapentenol, tribufos, trinexapac-ethyl, uniconazole P, 1-naphthylacetamide.

[0111] [Ectoparasite control agent] The ectoparasite-controlling agent of the present invention contains, as an active ingredient, at least one selected from the group consisting of Compound (I) and a salt of Compound (I). The amount of Compound (I) and a salt of Compound (I) contained in the ectoparasite-controlling agent of the present invention is not particularly limited as long as it exhibits an ectoparasite control effect.

[0112] The host animals to be treated with the ectoparasite control agent of the present invention include warm-blooded animals such as humans, domestic mammals (e.g., cattle, horses, pigs, sheep, goats, etc.), laboratory animals (e.g., mice, rats, gerbils, etc.), pet animals (e.g., hamsters, guinea pigs, dogs, cats, horses, squirrels, rabbits, ferrets, etc.), wild and zoo mammals (monkeys, foxes, deer, buffalo, etc.), poultry (turkeys, ducks, chickens, quails, geese, etc.), pet birds (pigeons, parrots, mynah birds, Java sparrows, parakeets, Bengalese finches, canaries, etc.); or fish such as salmon, trout, and koi carp. Other examples include honeybees, stag beetles, and rhinoceros beetles.

[0113] The ectoparasite-controlling agent of the present invention can be administered by known veterinary methods (topical, oral, parenteral, or subcutaneous administration). Examples of such methods include oral administration to animals via tablets, capsules, or incorporation into feed; administration to animals via immersion, suppository, or injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.); local administration of an oily or aqueous liquid formulation via spraying, pour-on, or spot-on; kneading the ectoparasite-controlling agent into a resin, molding the kneaded product into an appropriate shape such as a collar or ear tag, and attaching the resulting product to an animal for local administration; and the like.

[0114] Ectoparasites parasitize in and on host animals, particularly warm-blooded animals. Specifically, they infest the back, armpits, lower abdomen, inner thighs, etc. of the host animal and survive by obtaining nutrients such as blood and dander from the animal. Examples of ectoparasites include mites, lice, fleas, mosquitoes, stable flies, and flesh flies. Specific examples of ectoparasites that can be controlled by the ectoparasite control agent of the present invention are shown below.

[0115] (1) Mites (Acari) Mites that parasitize insects, such as mites of the Dermanyssidae family, mites of the Macronyssidae family, mites of the Laelapidae family, mites of the Varroidae family, mites of the Argasidae family, mites of the Ixodidae family, mites of the Psoroptidae family, mites of the Sarcoptidae family, mites of the Knemidokoptidae family, mites of the Demodixidae family, mites of the Trombiculidae family, and mites of the Stag Beetle family.

[0116] (2) Phthiraptera Lice of the family Haematopinidae, lice of the family Linognathidae, lice of the family Menoponidae, lice of the family Philopteridae, and lice of the family Trichodectidae.

[0117] (3) Siphonaptera Fleas of the family Pulicidae, for example, Ctenocephalides spp., dog flea (Ctenocephalides canis), cat flea (Ctenocephalides felis); Fleas of the Tungidae family, fleas of the Ceratophyllidae family, and fleas of the Leptopsyllidae family.

[0118] (4) Hemiptera.

[0119] (5) Diptera pests Mosquitoes of the Culicidae family, black flies of the Simuliidae family, midges of the Ceratopogonidae family, horseflies of the Tabanidae family, flies of the Muscidae family, sheathe flies of the Glossinidae family, flesh flies of the Sarcophagidae family, flies of the Hippoboscidae family, flies of the Calliphoridae family, and flies of the Oestridae family.

[0120] [Internal parasite control or extermination agent] The agent for controlling or eliminating endoparasites of the present invention contains, as an active ingredient, at least one compound selected from the group consisting of compound (I) and a salt of compound (I). The amount of compound (I) and a salt of compound (I) contained in the agent for controlling or eliminating endoparasites of the present invention is not particularly limited as long as it exhibits an effect of controlling endoparasites.

[0121] The parasites targeted by the endoparasite control or extermination agent of the present invention are parasitic (endoparasites) in host animals, particularly warm-blooded animals and fish. Examples of host animals for which the endoparasite control or extermination agent of the present invention is effective include warm-blooded animals such as humans, domestic mammals (e.g., cattle, horses, pigs, sheep, goats, etc.), laboratory animals (e.g., mice, rats, gerbils, etc.), pet animals (e.g., hamsters, guinea pigs, dogs, cats, horses, squirrels, rabbits, ferrets, etc.), wild and zoo mammals (monkeys, foxes, deer, buffalo, etc.), poultry (turkeys, ducks, chickens, quails, geese, etc.), pet birds (pigeons, parrots, mynah birds, Java sparrows, parakeets, Bengalese finches, canaries, etc.); or fish such as salmon, trout, and koi carp. Controlling and eliminating parasites can prevent or treat parasitic diseases transmitted by the parasites.

[0122] Parasites to be controlled or eradicated include the following: (1) Dioctophymatida nematodes (a) Kidney worms of the family Dioctophymatidae, e.g., Dioctophyma spp., Dioctophyma renale; (b) Kidneyworms of the family Soboliphymatidae, for example, Soboliphyme spp., Soboliphyme abei, Soboliphyme baturini.

[0123] (2) Nematodes of the order Trichocephalidae (a) Trichinella of the family Trichinellidae, such as Trichinella spiralis of the genus Trichinella spp.; (b) whipworms of the Trichuridae family, for example, Capillaria spp., such as Capillaria annulata, Capillaria contorta, Capillaria hepatica, Capillaria perforans, Capillaria plica, and Capillaria suis; Trichuris spp., such as Trichuris vulpis, Trichuris discolor, Trichuris ovis, Trichuris skrjabini, and Trichuris suis.

[0124] (3) Rhabditida nematodes Strongyloides of the family Strongyloididae, for example, Strongyloides spp., Strongyloides papillosus, Strongyloides planiceps, Strongyloides ransomi, Strongyloides suis, Strongyloides stercoralis, Strongyloides tumefaciens, and Strongyloides ratti.

[0125] (4) Strongylida nematodes Hookworms of the family Ancylostomatidae, for example, from the genus Ancylostoma (Ancylostoma spp.), Ancylostoma braziliense, Ancylostoma caninum, Ancylostoma duodenale, Ancylostoma tubaeforme; from the genus Uncinaria (Uncinaria stenocephala), Uncinaria stenocephala; from the genus Bunostomum (Bunostomum phlebotomum), Bunostomum trigonocephalum.

[0126] (5) Strongylida nematodes (a) Nematodes of the family Angiostrongylidae, for example, Aelurostrongylus spp., cat lungworm (Aelurostrongylus abstrusus); Angiostrongylus spp., Angiostrongylus vasorum, Angiostrongylus cantonesis; (b) Nematodes of the Crenosomatidae family, e.g., Crenosoma spp., Crenosoma aerophila, Crenosoma vulpis; (c) nematodes of the family Filaroididae, e.g., Filaroides spp., dog lungworm (Filaroides hirthi), Filaroides osleri; (d) lungworms of the family Metastrongylidae, for example, Metastrongylus spp., Metastrongylus apri, Metastrongylus asymmetricus, Metastrongylus pudendotectus, and Metastrongylus salmi; (e) Open-beaked worms of the Syngamidae family, for example, Cyathostoma spp., such as the waterfowl lungworm (Cyathostoma bronchialis); Syngamus spp., such as the scrijabinomorpha and the chicken open-beaked worm (Syngamus trachea).

[0127] (6) Strongylida nematodes (a) Nematodes of the family Molineidae, e.g., Nematodirus spp., Nematodirus filicollis, Nematodirus spathiger; (b) Nematodes of the family Dictyocaulidae, e.g., Dictyocaulus spp., Dictyocaulus filaria, Dictyocaulus viviparus; (c) Nematodes of the family Haemonchidae, for example, Haemonchus spp., Haemonchus contortus; Mecistocirrus spp., Mecistocirrus digitatus; (d) Nematodes of the family Haemonchidae, for example, Ostertagia spp., Ostertagia ostertagi; (e) Nematodes of the family Heligmonellidae, for example, Nippostrongylus spp., rat strongyle (Nippostrongylus braziliensis); (f) Nematodes of the Trichostrongylidae family, for example, Trichostrongylus spp., such as Trichostrongylus axei, Trichostrongylus colubriformis, and Trichostrongylus tenuis; Hyostrongylus spp., such as Hyostrongylus rubidus; and Obeliscoides spp., such as Obeliscoides cuniculi.

[0128] (7) Strongylida nematodes (a) Nematodes of the Chabertiidae family, for example, Chabertia spp., such as the sheep nematode Chabertia ovina; Oesophagostomum spp., such as Oesophagostomum brevicaudatum, Oesophagostomum columbianum, Oesophagostomum dentatum, Oesophagostomum georgianum, Oesophagostomum maplestonei, Oesophagostomum quadrispinulatum, Oesophagostomum radiatum, Oesophagostomum venulosum, and Oesophagostomum scrofa. watanabei); (b) Nematodes of the family Stephanuridae, e.g., Stephanurus spp., pig kidney worm (Stephanurus dentatus); (c) Nematodes of the Strongylidae family, for example, Strongylus spp., such as the donkey strongyle (Strongylus asini), the toothless strongyle (Strongylus edentatus), the horse strongyle (Strongylus equinus), and the common strongyle (Strongylus vulgaris).

[0129] (8) Nematodes of the order Oxyurida Nematodes of the family Oxyuridae, for example, Enterobius spp., chimpanzee pinworm (Enterobius anthropopitheci), pinworm (Enterobius vermicularis); Oxyuris spp., horse pinworms (Oxyuris equi); Passalurus spp., rabbit pinworms (Passalurus ambiguus).

[0130] (9) Nematodes of the order Ascaridida (a) Nematodes of the family Ascaridiidae, for example, Ascaridia spp., Ascaridia galli; (b) Nematodes of the family Heterakidae, such as Heterakis spp., Heterakis beramporia, Heterakis brevispiculum, Heterakis gallinarum, Heterakis pusilla, and Heterakis putaustralis; (c) Nematodes of the family Anisakidae, e.g., Anisakis spp. Anisakis simplex; (d) Nematodes of the family Ascarididae, for example, Ascaris spp., human roundworm (Ascaris lumbricoides), pig roundworm (Ascaris suum); Parascaris spp., horse roundworm (Parascaris equorum); (e) Nematodes of the family Toxocaridae, for example, Toxocara spp., such as Toxocara canis, Toxocara leonina, Toxocarasuum, Toxocara vitulorum, and Toxocara cati.

[0131] (10) Nematodes of the order Spirurida (a) Nematodes of the family Onchocercidae, for example, Brugia spp., such as Brugia malayi, Brugia pahangi, and Brugia patei; Dipetalonema spp., such as Dipetalonema reconditum; Dirofilaria spp., such as Dirofilaria immitis; Filaria spp., such as Filaria oculi; Onchocerca spp., such as Onchocerca cervicalis and Onchocerca gibsoni; Pharyngeal heartworm (Onchocerca gutturosa); (b) Nematodes of the Setariidae family, for example, Setaria spp., such as Setaria digitata, Setaria equina, Setaria labiatopapillosa, and Setaria marshalli; Wuchereria spp., such as Wuchereria bancrofti; (c) Nematodes of the family Filariidae, for example, Parafilaria spp., such as Parafilaria multipapillosa; Stephanofilaria spp., such as Stephanofilaria assamensis, Stephanofilaria dedoesi, Stephanofilaria kaeli, Stephanofilaria okinawaensis, and Stephanofilaria stilesi.

[0132] (11) Nematodes of the order Spirurida (a) Nematodes of the family Gnathostomatidae, e.g., Gnathostoma spp., Gnathostoma doloresi, Gnathostoma spinigerum; (b) Nematodes of the family Habronematidae, for example, Habronema spp., such as Habronema majus, Habronema microstoma, and Habronema muscae; Draschia spp., such as Draschia megastoma; (c) Nematodes of the family Physalopteridae, for example, Physaloptera spp., such as Physaloptera canis, Physaloptera cesticillata, Physaloptera erdocyona, Physaloptera felidis, Physaloptera gemina, Physaloptera papilloradiata, Physaloptera praeputialis, Physaloptera pseudopraerutialis, Physaloptera rara, and Physaloptera sibirica. sibirica), Physaloptera vulpineus; (d) Nematodes of the family Gongylonematidae, e.g., Gongylonema spp., Gongylonema pulchrum; (e) Nematodes of the family Spirocercidae, e.g., Ascarops spp., Ascarops strongylina; (f) Nematodes of the family Thelaziidae, for example, Thelazia spp., such as Thelazia callipaeda, Thelazia gulosa, Thelazia lacrymalis, Thelazia rhodesi, and Thelazia skrjabini.

[0133] [Control agents for other pests] The carbamate compounds of the present invention are also effective in controlling pests that have poisonous stingers or venom and cause harm to humans and animals, pests that transmit various pathogens and pathogenic bacteria, and pests that cause discomfort to humans (poisonous pests, sanitary pests, nuisance pests, etc.).

[0134] A specific example is given below. (1) Hymenoptera pests Wasps of the Argidae family, Cynipidae family, Diprionidae family, Formicidae family, Mutillidae family, and Vespidae family.

[0135] (2) Other pests Cockroaches (Blattodea), termites (termite), spiders (Araneae), centipedes (cetipede), millipedes (millipede), crustaceans (crustacea), bedbugs (Cimex lectularius).

[0136] [Formulation] Some formulations of the pesticide, insecticide or acaricide, ectoparasite control agent, or endoparasite control or extermination agent of the present invention are shown below, but the additives and their addition ratios should not be limited to these examples and can be varied over a wide range. Parts in the formulations are parts by weight.

[0137] The formulations for agricultural and horticultural use and for paddy rice are shown below.

[0138] (Formulation 1: Wettable powder) 40 parts of the carbamate compound of the present invention, 53 parts of diatomaceous earth, 4 parts of higher alcohol sulfate, and 3 parts of alkylnaphthalene sulfonate are uniformly mixed and finely pulverized to obtain a wettable powder containing 40% of the active ingredient.

[0139] (Formulation 2: emulsion) 30 parts of the carbamate compound of the present invention, 33 parts of xylene, 30 parts of dimethylformamide, and 7 parts of polyoxyethylene alkyl allyl ether are mixed and dissolved to obtain an emulsifiable concentrate containing 30% of the active ingredient.

[0140] (Formulation 3: Granules) Five parts of the carbamate compound of the present invention, 40 parts of talc, 38 parts of clay, 10 parts of bentonite, and 7 parts of sodium alkyl sulfate are uniformly mixed and finely ground, and then granulated into granules with a diameter of 0.5 to 1.0 mm to obtain granules containing 5% of the active ingredient.

[0141] (Formulation 4: Granules) Five parts of the carbamate compound of the present invention, 73 parts of clay, 20 parts of bentonite, 1 part of dioctyl sulfosuccinate sodium salt, and 1 part of potassium phosphate are thoroughly ground and mixed, water is added, the mixture is thoroughly kneaded, and the mixture is granulated and dried to obtain granules containing 5% of the active ingredient.

[0142] (Formulation 5: Suspension) 10 parts of the carbamate compound of the present invention, 4 parts of polyoxyethylene alkyl allyl ether, 2 parts of polycarboxylic acid sodium salt, 10 parts of glycerin, 0.2 parts of xanthan gum, and 73.8 parts of water are mixed and wet-pulverized until the particle size is 3 microns or less, to obtain a suspension containing 10% of the active ingredient.

[0143] The formulations for external parasite control agents or internal parasite control or extermination agents are shown below.

[0144] (Formulation 6: Granules) 5 parts of the carbamate compound of the present invention are dissolved in an organic solvent to obtain a solution, which is then sprayed onto 94 parts of kaolin and 1 part of white carbon, and the solvent is then evaporated under reduced pressure. This type of granule can be mixed with animal feed.

[0145] (Formulation 7: Injection) 0.1 to 1 part of the carbamate compound of the present invention and 99 to 99.9 parts of peanut oil are mixed uniformly, and then sterilized by filtration using a sterilizing filter.

[0146] (Formulation 8: pour-on) A pour-on agent is obtained by uniformly mixing 5 parts of the carbamate compound of the present invention, 10 parts of myristate ester, and 85 parts of isopropanol.

[0147] (Formulation 9: Spot-on) A spot-on agent is obtained by uniformly mixing 10 to 15 parts of the carbamate compound of the present invention, 10 parts of palmitic acid ester, and 75 to 80 parts of isopropanol.

[0148] (Formulation 10: Spray) A spray agent is obtained by uniformly mixing 1 part of the carbamate compound of the present invention, 10 parts of propylene glycol, and 89 parts of isopropanol.

[0149] Next, the present invention will be explained in more detail by showing synthesis examples, but the present invention is not limited to the following synthesis examples.

[0150] (Synthesis Example 1) TIFF2026014715000018.tif67149

[0151] 2,4-Bis(trifluoromethyl)aniline (0.27 g) and triethylamine (0.15 g) were dissolved in tetrahydrofuran (5 mL), and the resulting solution was cooled to 0°C. To this was added triphosgene (0.14 g), and the mixture was stirred at 0°C for 1 hour. To the resulting solution was added 1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethanol (0.15 g), and the mixture was stirred at room temperature overnight. The solvent was then evaporated under reduced pressure. Thereafter, purification by silica gel column chromatography was carried out to obtain 1-(1-pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl)ethyl (2,4-bis(trifluoromethyl)phenyl)carbamate represented by formula (A-1) [English name: 1-(1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl)ethyl (2,4-bis(trifluoromethyl)phenyl)carbamate] (compound (A-1), yield 0.05 g, melting point (mp) = 187-189°C).

[0152] (Synthesis Example 2) A compound represented by formula (A-2) (compound (A-2), yield 0.05 g, melting point (mp) = 180-181°C) was obtained in the same manner as in Synthesis Example 1, except that 2,4-bis(trifluoromethyl)aniline was changed to 2-chloro-4-trifluoromethyl-aniline.

[0153] TIFF2026014715000019.tif3076

[0154] [Biological Testing] The usefulness of the carbamate compounds of the present invention as active ingredients of pesticides will be demonstrated in the following test examples. "Parts" are by mass.

[0155] 5 parts of the carbamate compound of the present invention as an active ingredient, 93.6 parts of dimethylformamide, and 1.4 parts of polyoxyethylene alkylaryl ether were mixed and dissolved to obtain an emulsifiable concentrate (I) containing 5% by mass of the active ingredient. 93.6 parts of dimethylformamide and 1.4 parts of polyoxyethylene alkylaryl ether were mixed and dissolved to obtain emulsion (II).

[0156] (1) Efficacy test against armyworm (1) Emulsifiable concentrate (I) was diluted with water to an active ingredient concentration of 125 ppm. Corn leaves were immersed in the diluted solution for 30 seconds. The corn leaves were placed in a petri dish, and five second-instar armyworm larvae were released into the dish. The dish was placed in a thermostatic chamber at a temperature of 25°C and a humidity of 60%. Six days after release, survival was assessed, and the insecticidal rate was calculated. The test was performed in duplicate.

[0157] Compounds (A-1) and (A-2) were tested for efficacy against the armyworm (Pseudaletia separata) (1). Both compounds showed an insecticidal rate of 80% or more against the armyworm.

[0158] (2) Efficacy test against armyworm (2) The test diet was prepared by mixing 0.8 g of commercially available artificial diet (Insector LFS, manufactured by Nippon Nosan Kogyo Co., Ltd.) with 1 μl of emulsion (I). The control diet was prepared by mixing 0.8 g of commercially available artificial diet (Insector LFS, manufactured by Nippon Nosan Kogyo Co., Ltd.) with 1 μl of emulsion (II). 0.2 g of the test diet was placed in a plastic container (1.4 ml volume) (treatment group). 0.2 g of the control diet was placed in a plastic container (1.4 ml volume) (control group). Two second-instar larvae of the armyworm were released into each container and sealed with a plastic lid. These were then placed in a constant temperature room at 25°C. Five days after release, the mortality rate and feeding amount were determined. The test was conducted in two replicates.

[0159] Compounds (A-1) and (A-2) were tested for efficacy against the armyworm (Pseudaletia separata) in a test (2). Both compounds showed a 100% mortality rate against the armyworm, and the feeding rate was 10% or less compared to the control.

[0160] (3) Efficacy test against diamondback moth Emulsifiable concentrate (I) was diluted with water to an active ingredient concentration of 125 ppm. Cabbage leaves were immersed in the diluted solution for 30 seconds. The cabbage leaves were placed in a petri dish, and five second-instar diamondback moth larvae were released into the dish. The dish was placed in a thermostatic chamber at a temperature of 25°C and a humidity of 60%. Three days after release, the animals were counted as dead or alive, and the insecticidal rate was calculated. The test was performed in duplicate.

[0161] Compounds (A-1) and (A-2) were tested for efficacy against diamondback moth, and both compounds showed insecticidal rates of 80% or more.

[0162] Since compounds randomly selected from the compounds of the present invention exhibit the effects described above, it can be understood that the compounds of the present invention, including those not fully demonstrated in the examples, have effects such as pest control, acaricidal, and insecticidal.

Claims

1. A compound represented by formula (I) or a salt thereof: [In formula (I), R 1 represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylcarbonyl group, or a substituted or unsubstituted C1-6 alkoxycarbonyl group, R ２ and R ３ each independently represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group, Y 1 and Y 2 are each independently a nitrogen atom or CR a represents a group represented by R a represents a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C3-6 cycloalkyl group, and Q 1 and Q 2 each independently represents a substituted or unsubstituted 5-membered heteroaryl group, a substituted or unsubstituted 6-membered heteroaryl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted fused bicyclic 10- to 12-membered heteroaryl group.

2. A pesticide comprising at least one compound selected from the group consisting of the compound according to claim 1 and a salt thereof as an active ingredient.

3. 10. An insecticide or acaricide containing at least one compound selected from the group consisting of the compound according to claim 1 and a salt thereof as an active ingredient.

4. An ectoparasite control agent comprising at least one compound selected from the group consisting of the compound according to claim 1 and a salt thereof as an active ingredient.

5. An agent for controlling or eliminating internal parasites, comprising at least one selected from the group consisting of the compound according to claim 1 and a salt thereof as an active ingredient.

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