Imidazolyl azole compound and pest control agent

Abstract

To provide an imidazolyl azole compound that exhibits superior insecticidal and / or acaricidal activities, has superior safety, and can be synthesized with industrial advantage, and also to provide a pest control agent comprising the compound as an active ingredient.SOLUTION: A compound represented by formula (I-1a) or the like, or a salt thereof. [In the formula, R1 represents a substituted or unsubstituted C1-6 alkyl group or the like, R2 represents a substituted or unsubstituted C1-6 alkyl group, and R4 represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, or the like].SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to an imidazolyl azole compound and a pesticide. More specifically, the present invention relates to an imidazolyl azole compound that has excellent insecticidal and / or acaricidal activity, is highly safe, and can be synthesized industrially in an advantageous manner, and to a pesticide 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 discloses compounds represented by formula (A), formula (B), and the like.

[0004] TIFF2025134093000001.tif61150

[0005] TIFF2025134093000002.tif61150 [Prior art documents] [Patent documents]

[0006] [Patent Document 1] WO2019 / 189731 A1 Summary of the Invention [Problem to be solved by the invention]

[0007] An object of the present invention is to provide an imidazolyl azole compound that has excellent pest control activity, particularly excellent insecticidal and / or acaricidal activity, is excellent in safety, and can be synthesized industrially advantageously.Another object of the present invention is to provide a pest control agent, insecticide or acaricide, ectoparasite control agent, or endoparasite control or extermination agent containing the imidazolyl azole compound as an active ingredient. [Means for solving the problem]

[0008] As a result of intensive research aimed at solving the above problems, the present invention has been completed, including the following aspects. [1] A compound represented by formula (I) or a salt thereof: AB (I) [In formula (I), A is a group represented by formula (A1) or a group represented by formula (A2), TIFF2025134093000003.tif29150 TIFF2025134093000004.tif29150 In formulas (A1) and (A2), * indicates the binding site with B, R 1 is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, or a substituted or unsubstituted phenyl group, R 2 is a substituted or unsubstituted C1-6 alkyl group, R 3 is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, an amino group, a cyano group, or a halogeno group, In formula (I), B is a group represented by formula (B1) or a group represented by formula (B2), TIFF2025134093000005.tif42150 TIFF2025134093000006.tif42150 In formulas (B1) and (B2), * indicates the binding site with A, R 4 represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5-10 membered heterocyclyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aminocarbonyl group, -C(=N-OR a )R b a nitro group, a cyano group, or a halogeno group; R a is a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group, R b is a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group, R 5 is a substituted or unsubstituted C1-6 alkyl group or a substituted or unsubstituted C3-6 cycloalkyl group, n represents the number of O and is 0, 1, or 2.

[0009] [2] A pesticide containing at least one selected from the group consisting of the compound according to [1] above and a salt thereof as an active ingredient. [3] An insecticide or acaricide containing, as an active ingredient, at least one selected from the group consisting of the compound according to [1] above and a salt thereof. [4] An ectoparasite control agent containing, as an active ingredient, at least one selected from the group consisting of the compound according to [1] above and a salt thereof. [5] An agent for controlling or eliminating internal parasites, comprising at least one selected from the group consisting of the compound according to [1] above and salts thereof as an active ingredient. [Effects of the Invention]

[0010] The imidazolyl azole compound of the present invention (a compound represented by formula (I) or a salt thereof) can control pests that pose problems in terms of agricultural crops and hygiene. The imidazolyl azole compound of the present invention can effectively control agricultural pests and mites, in particular, at lower concentrations. The imidazolyl azole compound of the present invention can also effectively control ectoparasites and endoparasites that harm humans and livestock. DETAILED DESCRIPTION OF THE INVENTION

[0011] The imidazolyl azole compound of the present invention is a compound represented by formula (I) (hereinafter, may be referred to as compound (I)) or a salt of compound (I). In other words, the imidazolyl azole compound of the present invention is a compound represented by formula (I-1) (hereinafter, may be referred to as compound (I-1)), a salt of compound (I-1), a compound represented by formula (I-2) (hereinafter, may be referred to as compound (I-2)), a salt of compound (I-2), a compound represented by formula (I-3) (hereinafter, may be referred to as compound (I-3)), a salt of compound (I-3), a compound represented by formula (I-4) (hereinafter, may be referred to as compound (I-4)), or a salt of compound (I-4).

[0012] TIFF2025134093000007.tif48150

[0013] TIFF2025134093000008.tif48150

[0014] TIFF2025134093000009.tif48150

[0015] TIFF2025134093000010.tif48150

[0016] 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. The "substituent" is not particularly limited as long as it is chemically permissible and has the effect of the present invention.

[0017] Examples of groups that can be "substituents" are shown 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 (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;

[0018] C3-6 cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl; Phenyl group, naphthyl group; phenyl C1-6 alkyl groups such as benzyl and phenethyl groups; 3- to 6-membered heterocyclyl groups; 3-6 membered heterocyclyl C1-6 alkyl group;

[0019] 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; Phenoxy group, naphthoxy group; phenyl C1-6 alkoxy groups such as benzyloxy 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;

[0020] 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;

[0021] halogeno groups such as fluoro, chloro, bromo, and iodo groups; C1-6 haloalkyl groups such as a chloromethyl group, a chloroethyl group, a trifluoromethyl group, a 1,2-dichloro-n-propyl group, a 1-fluoro-n-butyl group, and a perfluoro-n-pentyl 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;

[0022] amino group; C1-6 alkyl-substituted amino groups such as methylamino, dimethylamino, and diethylamino; Anilino group, naphthylamino group; phenyl C1-6 alkylamino groups such as benzylamino 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 an aminocarbonyl group, a dimethylaminocarbonyl group, a phenylaminocarbonyl group, or an N-phenyl-N-methylaminocarbonyl group; 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; Aminocarbonyloxy group; C1-6 alkyl-substituted aminocarbonyloxy groups such as an ethylaminocarbonyloxy group and a dimethylaminocarbonyloxy group;

[0023] 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;

[0024] 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;

[0025] 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;

[0026] tri-C1-6 alkyl-substituted silyl groups such as trimethylsilyl, triethylsilyl, and t-butyldimethylsilyl; Triphenylsilyl group; Cyano group; nitro group.

[0027] 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.

[0028] The "3- to 6-membered heterocyclyl group" refers to a group containing 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur atoms as ring-constituting atoms. The heterocyclyl group may be either monocyclic or polycyclic. In a polycyclic heterocyclyl group, as long as at least one ring is a heterocycle, the remaining rings may be saturated alicyclic, unsaturated alicyclic, or aromatic. Examples of the "3- to 6-membered heterocyclyl group" include 3- to 6-membered saturated heterocyclyl groups, 5- to 6-membered heteroaryl groups, and 5- to 6-membered partially unsaturated heterocyclyl groups.

[0029] Examples of the "3- to 6-membered saturated heterocyclyl group" include an aziridinyl group, an epoxy 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.

[0030] Examples of the "5-membered heteroaryl group" include a pyrrolyl group, 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. Examples of the "5- to 6-membered partially unsaturated heterocyclyl group" include 5-membered partially unsaturated heterocyclyl groups such as a pyrrolinyl group, a dihydrofuranyl group, a dihydrothiophenyl group, an imidazolinyl group, a pyrazolinyl group, an oxazolinyl group, an isoxazolinyl group, a thiazolinyl group, and an isothiazolinyl group; and 6-membered partially unsaturated heterocyclyl groups such as a dihydropyranyl group.

[0031] R in formulas (I-1), (I-2), (I-3) and (I-4) 1 is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, or a substituted or unsubstituted phenyl group.

[0032] R 1 The "C1-6 alkyl group" in the above may be a straight chain or a branched chain. Examples of the "C1-6 alkyl group" include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an i-propyl group, an i-butyl group, an s-butyl group, a t-butyl group, an i-pentyl group, a neopentyl group, a 2-methylbutyl group, and an i-hexyl group.

[0033] R 1 Examples of the "C2-6 alkenyl group" in the above formula include a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-methyl-2-propenyl group, a 2-methyl-2-propenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 4-pentenyl group, a 1-methyl-2-butenyl group, a 2-methyl-2-butenyl group, a 1-hexenyl group, a 2-hexenyl group, a 3-hexenyl group, a 4-hexenyl group, and a 5-hexenyl group.

[0034] R 1As the substituent on the "C1-6 alkyl group" or "C2-6 alkenyl group" in a halogeno group, a hydroxyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, a phenyl group, a 5-membered heteroaryl group, a 6-membered heteroaryl group, or a cyano group; a phenyl group substituted by one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, and a C1-6 haloalkoxy group; a 5-membered heteroaryl group substituted by one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, and a C1-6 haloalkoxy group; or A 6-membered heteroaryl group substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, and a C1-6 haloalkoxy group is preferred.

[0035] R 1 The substituents on the "phenyl group" in a halogeno group, a C1-6 alkyl group, a C1-6 haloalkyl group, a hydroxyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, a phenyl group, a 5-membered heteroaryl group, a 6-membered heteroaryl group, or a cyano group; a phenyl group substituted by one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, and a C1-6 haloalkoxy group; a 5-membered heteroaryl group substituted by one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, and a C1-6 haloalkoxy group; or A 6-membered heteroaryl group substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, and a C1-6 haloalkoxy group is preferred. R 1The "substituted phenyl group" in the above formula (I) is a "phenyl group" having one or more substituents thereon, and the multiple substituents may be bonded to each other to form a ring, which may be either a saturated alicyclic ring or an unsaturated alicyclic ring. Examples of the "substituted phenyl group" include an indenyl group, an indanyl group, a tetrahydronaphthyl group, a dihydronaphthyl group, a tolyl group, a xylyl group, a mesityl group, and a dulyl group.

[0036] R in formulas (I-1) and (I-2) 2 is a substituted or unsubstituted C1-6 alkyl group. R 2 The "substituted or unsubstituted C1-6 alkyl group" in the above R 1 The same examples as those exemplified above can be mentioned.

[0037] R in formulas (I-3) and (I-4) 3 is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, an amino group (a group represented by -NH3), a cyano group, or a halogeno group.

[0038] R 3 The "substituted or unsubstituted C1-6 alkyl group" in the above R 1 The same examples as those exemplified above can be mentioned.

[0039] R 3 Examples of the "halogeno group" in the above formula include a fluoro group, a chloro group, a bromo group, and an iodo group.

[0040] R in formulas (I-1), (I-2), (I-3) and (I-4) 4represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5-10 membered heterocyclyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aminocarbonyl group, -C(=N-OR a )R b a nitro group, a cyano group, or a halogeno group.

[0041] R 4 The "substituted or unsubstituted C1-6 alkyl group" and "substituted or unsubstituted C2-6 alkenyl group" in the above R 1 The same examples as those exemplified above can be mentioned.

[0042] R 4 Examples of the "C2-6 alkynyl group" in the above formula include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 1-methyl-2-propynyl group, a 2-methyl-3-butynyl group, a 1-pentynyl group, a 2-pentynyl group, a 3-pentynyl group, a 4-pentynyl group, a 1-methyl-2-butynyl group, a 2-methyl-3-pentynyl group, a 1-hexynyl group, and a 1,1-dimethyl-2-butynyl group.

[0043] R 4 Examples of the "C1-6 alkylcarbonyl group" in the above formula include an acetyl group, propionyl, n-propylcarbonyl group, i-propylcarbonyl group, n-butylcarbonyl group, and t-butylcarbonyl group.

[0044] R 4Examples 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.

[0045] R 4 In the above, the substituents on the "C1-6 alkyl group", "C2-6 alkenyl group", "C2-6 alkynyl group", "C1-6 alkylcarbonyl group", or "C1-6 alkoxycarbonyl group" include: a halogeno group, a hydroxyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, a phenyl group, a 5-membered heteroaryl group, a 6-membered heteroaryl group, or a cyano group; a phenyl group substituted by one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, and a C1-6 haloalkoxy group; a 5-membered heteroaryl group substituted by one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, and a C1-6 haloalkoxy group; or A 6-membered heteroaryl group substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, and a C1-6 haloalkoxy group is preferred.

[0046] R 4 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.

[0047] R 4 The "5- to 10-membered heterocyclyl group" in the above is a group containing 1, 2, 3, or 4 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur atoms as ring-constituting atoms. When there are two or more heteroatoms, they may be the same or different. The ring may be either monocyclic or polycyclic. Examples of the "5- to 10-membered heterocyclyl group" include a 5- to 10-membered saturated heterocyclyl group, a 5- to 10-membered heteroaryl group, and a 5- to 10-membered partially unsaturated heterocyclyl group.

[0048] Examples of the 5- to 10-membered saturated heterocyclyl group include a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a tetrahydro-2H-pyranyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a dioxolanyl group, and a dioxanyl group. Examples of the 5-membered heteroaryl group include a pyrrolyl group, 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. Examples of the 7-membered heteroaryl group include a 3-azabicyclo[3.2.0]heptane-1,4-dien-2-yl group and a 3-azabicyclo[3.2.0]heptane-1,4,6-trien-6-yl group. Examples of the 8-membered heteroaryl group include a 2,4,5,6-tetrahydrocyclopenta[c]pyrrol-2-yl group and a 2,4-dihydrocyclopenta[c]pyrrol-4-yl group. Examples of the 9-membered heteroaryl group include an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothienyl group, an indazolyl group, a benzimidazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a benzothiazolyl group, and a benzisothiazolyl group. Examples of the 10-membered heteroaryl group include a quinolinyl group, an isoquinolinyl group, a cinnolinyl group, a phthalazinyl group, a quinazolinyl group, and a quinoxalinyl group.

[0049] Examples of 5- to 10-membered partially unsaturated heterocyclyl groups include 5-membered partially unsaturated heterocyclyl groups such as pyrrolinyl, dihydrofuranyl, imidazolinyl, pyrazolinyl, oxazolinyl, and isoxazolinyl groups; 6-membered partially unsaturated heterocyclyl groups such as dihydropyranyl groups; 9-membered partially unsaturated heterocyclyl groups such as indolinyl, isoindolinyl, 2,3-dihydrobenzofuranyl, and 1,3-dihydrobenzofuranyl groups; and 10-membered partially unsaturated heterocyclyl groups such as 1,2,3,4-tetrahydroquinolinyl groups.

[0050] R 4 In the above, examples of the substituents on the "C3-6 cycloalkyl group", "phenyl group", "naphthyl group", or "5- to 10-membered heterocyclyl group" include: a halogeno group, a C1-6 alkyl group, a C1-6 haloalkyl group, a hydroxyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, a phenyl group, a 5-membered heteroaryl group, a 6-membered heteroaryl group, or a cyano group; a phenyl group substituted by one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, and a C1-6 haloalkoxy group; a 5-membered heteroaryl group substituted by one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, and a C1-6 haloalkoxy group; or A 6-membered heteroaryl group substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, and a C1-6 haloalkoxy group is preferred.

[0051] R 4The "substituted phenyl group" or "substituted naphthyl group" in the above formula (I) has one or more substituents on the "phenyl group" or "naphthyl group," and the multiple substituents may be bonded to each other to form a ring, which may be either a saturated alicyclic ring or an unsaturated alicyclic ring. Examples of the "substituted phenyl group" or "substituted naphthyl group" include an indenyl group, an indanyl group, a tetrahydronaphthyl group, a dihydronaphthyl group, a tolyl group, a xylyl group, a mesityl group, and a duryl group.

[0052] R 4 The "substituted or unsubstituted amino group" in c R d " is a group represented by R 4 The "substituted or unsubstituted aminocarbonyl group" in c R d " is a group represented by the formula: c and R d may each independently be a hydrogen atom, a C1-6 alkyl group, a formyl group, a C1-6 alkylcarbonyl group, a substituted or unsubstituted aminocarbonyl group, or the like. R 4 Examples of the "substituted or unsubstituted amino group" in the above formula include an amino group, a methylamino group, an ethylamino group, and a dimethylamino group. R 4 Examples of the "substituted or unsubstituted aminocarbonyl group" in the above formula include a methylaminocarbonyl group, an ethylaminocarbonyl group, and a dimethylaminocarbonyl group.

[0053] R c and R d The "C1-6 alkyl group" in R 1 The same examples as those exemplified above can be mentioned.

[0054] R c and R d Examples of the "C1-6 alkylcarbonyl group" in the above formula include an acetyl group and a propionyl group.

[0055] R c and R d The "substituted or unsubstituted aminocarbonyl group" in e R f " is a group represented by the formula: e and R f R are each independently a hydrogen atom, a C1-6 alkyl group, a formyl group, a C1-6 alkylcarbonyl group, a substituted or unsubstituted aminocarbonyl group, etc. e and R f In the above, the "C1-6 alkyl group", "C1-6 alkylcarbonyl group", and "substituted or unsubstituted aminocarbonyl group" are R c and R d The same examples as those exemplified above can be mentioned.

[0056] -C(=N-OR a )R b R in the group represented by a is a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group, and R b is a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group.

[0057] R a and R b The "substituted or unsubstituted C1-6 alkyl group" in 1 The same examples as those exemplified above can be mentioned.

[0058] R in formulas (I-1), (I-2), (I-3) and (I-4) 5 is a substituted or unsubstituted C1-6 alkyl group or a substituted or unsubstituted C3-6 cycloalkyl group. R 5 The "substituted or unsubstituted C1-6 alkyl group" in 1 The same examples as those given in R 5Specific examples of the "substituted or unsubstituted C1-6 alkyl group" in the above formula include C3-6 cycloalkyl C1-6 alkyl groups such as cyclopropylmethyl group. R 5 The "substituted or unsubstituted C3-6 cycloalkyl group" in 4 The same examples as those exemplified above can be mentioned.

[0059] In formulas (I-1), (I-2), (I-3) and (I-4), n represents the number of O and is 0, 1 or 2. That is, R 5 -S(O) n The group represented by - is R 5 -S-, R 5 A group represented by -SO- or R 5 This represents a group represented by -SO2-.

[0060] 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; ammonia; salts of organic bases such as triethylamine, tributylamine, pyridine, and hydrazine.

[0061] 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) can be obtained by a known production method described in the Examples, etc. Furthermore, a salt of Compound (I) can be obtained from Compound (I) by a known method.

[0062] The imidazolyl azole compound of the present invention (hereinafter referred to as "the compound of the present invention") is highly effective in controlling various agricultural pests and harmful organisms such as mites that affect plant growth. Furthermore, the 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 compound of the present invention exhibits excellent control effects not only against susceptible pests, but also against various resistant pests and even against acaricide-resistant mites.

[0063] The compound of the present invention is highly effective in controlling ectoparasites and endoparasites that are harmful to humans and animals. Furthermore, it is a highly safe substance due to its low toxicity to fish and warm-blooded animals. Therefore, it is useful as an active ingredient in an agent for controlling ectoparasites and endoparasites.

[0064] Furthermore, the 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] [Pest control agents] The pesticide of the present invention contains at least one compound selected from the compounds of the present invention as an active ingredient. The amount of the compound of the present invention 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 compound selected from the compounds of the present invention as an active ingredient. The amount of the compound of the present invention contained in the insecticide or acaricide of the present invention is not particularly limited as long as it shows 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 grasses, turf grasses, 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). 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.

[0068] Specific examples of various agricultural pests and mites that can be controlled by the pest control agent of the present invention are shown below.

[0069] (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;

[0070] (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, Spodoptera litura; for example, Autographa spp., such as Autographa gamma and Autographa nigrisigna; for example, Agrotis spp., such as Agrotis ipsilon and Agrotis nigrisigna. Helicoverpa spp., such as the cotton bollworm (Helicoverpa armigera), the tobacco budworm (Helicoverpa assulta), and the cotton bollworm (Helicoverpa zea); Heliothis spp., such as the cotton bollworm (Heliothis armigera), Heliothis virescens; other insects include Aedia leucomelas, Ctenoplusia agnata, Eudocima tyrannus, Mamestra brassicae, Mythimna separata, and the Japanese armyworm. Biko moth (Naranga aenescens), pine sawfly moth (Panolis japonica), false stag bean moth (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, e.g., Pieris spp. ) large cabbage white butterfly (Pieris brassicae), cabbage white butterfly (Pieris rapae crucivora); (o) Moths of the Plutellidae family, for example, Acrolepiopsis spp., such as Acrolepiopsis sapporensis and Acrolepiopsis suzukiella; and others, such as 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);

[0071] (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).

[0072] (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.

[0073] (3) Hemiptera pests (A)Archaeorrhyncha (a) Delphacidae, for example, Laodelphax striatella, Nilaparvata lugens, Perkinsiella saccharicida, and Sogatella furcifera.

[0074] (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-legged leafhopper (Balclutha saltuella), giant leafhopper (Epiacanthus stramineus), small leafhopper (Macrosteles striifrons), green rice leafhopper (Nephotettix cinctinceps).

[0075] (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);

[0076] (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.

[0077] (D) Sternorrhyncha (a) Adelgidae, e.g., Adelges laricis; (b) Aleyrodidae, for example, Bemisia spp., such as the silverleaf whitefly (Bemisia argentifolii) and the tobacco whitefly (Bemisia tabaci); and others, such as the citrus spiny whitefly (Aleurocanthus spiniferus), the citrus whitefly (Dialeurodes citri), and the greenhouse whitefly (Trialeurodes vaporariorum); (c) from the family Aphididae, for example, from the genus Aphis (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); from the genus Rhopalosiphum (Rhopalosiphum spp.), such as the corn aphid (Rhopalosiphum maidis) and the wheat aphid (Rhopalosiphum padi); from the genus Dysaphis (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);.

[0078] (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).

[0079] (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);

[0080] (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, from the genus Sitophilus, 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).

[0081] (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).

[0082] (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).

[0083] (6) Orthoptera pests (a) The grasshoppers (Acrididae), for example, the American locust (Schistocerca americana) and the desert locust (Schistocerca gregaria) of the Schistocerca spp.; other grasshoppers such as the Australian locust (Chortoicetes terminifera), the Moroccan locust (Dociostaurus maroccanus), the migratory locust (Locusta migratoria), the brown locust (Locustana pardalina), and the red locust (Nomadacris septemfasciata); 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).

[0084] (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.

[0085] (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 kanzawai, Tetranychus ludeni, Tetranychus quercivorus, Tetranychus phaselus, Tetranychus urticae, Tetranychus viennensis, Tetranychus evansi; 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.

[0086] (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.

[0087] 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. The combination of the compound of the present invention with other active ingredients is expected to produce a synergistic effect in terms of insecticidal, acaricidal and nematicidal activities. 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.

[0088] Specific examples of insecticides and acaricides that can be mixed or used in combination with the pest control agent of the present invention are shown below. (1B) Acetylcholinesterase (AChE) inhibitors (organophosphates) Acephate, Azamethiphos, Azinphos-ethyl, Azinphos-methyl, Cadusafos, Chlorethoxyfos, Chlorfenvinphos, Chlormephos, Chlorpyrifos, Chlorpyrifos-methyl, Coumaphos, Cyanophos, Demeton-S-methyl, Diazinon, Dichlorvos DDVP), Dicrotophos, Dimethoate, Dimethylvinphos, Disulfoton, EPN, Ethion, Ethoprophos, Famphur, Fenamiphos, Fenitrothion, Fenthion, Fosthiazate, Heptenophos, Imicyafos, Isofenphos, Isopropyl O-(methoxyaminothio-phosphoryl) salicylatesalicylate, Isoxathion, Malathion, Mecarbam, Methamidophos, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion, Parathion-methyl, Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimiphos-methyl methyl), profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, vamidothion. Bromophos-ethyl, Cyanofenphos, Demeton-S-methylsulfone, Dialifos, Dichlofenthion, Dioxabenzofos, Etrimfos, Fensulfothion, Fonofos, Formothion, Iodofenphos, Isazofos, Isocarbofos, Methacrifos, Phosphocarb, Pirimiphos-ethyl, Propaphos, Prothoate, Sulprofos.

[0089] (2) GABAergic chloride channel blockers Chlordane, Endosulfan; Ethiprole, Fipronil. Acetoprole, Camphechlor, Dienochlor, Heptachlor, Pyrafluprole, Pyriprole; Flufiprole. (3A) Sodium channel modulators (pyrethroids) Acrinathrin, Allethrin, d-cis-trans-Allethrin, d-trans-Allethrin, Bifenthrin, Bioallethrin, Bioallethrin-S-cyclopentenyl-isomer S-cyclopentenyl-isomer, Bioresmethrin, Cycloprothrin, Cyfluthrin, β-Cyfluthrin, Cyhalothrin, λ-Cyhalothrin, γ-Cyhalothrin, Cypermethrin, α-Cypermethrin, β-Cypermethrin, theta-Cypermethrin, ζ-Cypermethrin, Cyphenothrin [(1R)-trans-isomers] ), Deltamethrin, Empenthrin [(EZ)-(1R)-isomers], Esfenvalerate, Etofenprox, Fenpropathrin, Fenvalerate, Flucythrinate, Flumethrin, tau-Fluvalinate, Halfenprox, Imiprothrin, Kadethrin, Permethrin, Phenothrin [(1R)-trans-isomer]), Prallethrin, Pyrethrins, Resmethrin, Silafluofen, Tefluthrin, Tetramethrin, Tetramethrin [(1R)-isomers], Tralomethrin, Transfluthrin. κ-Bifenthrin, Biopermethrin, Chloroprallethrin, Dimefluthrin, Fenfluthrin, Fenpirithrin, Flufenprox, Heptafluthrin, Meperfluthrin, ε-Metofluthrin ), Momfluorothrin, epsilon-Momfluorothrin, trans-Permethrin, Profluthrin, Protrifenbute, kappa-Tefluthrin, Terallethrin, Tetramethylfluthrin; Bioethanomethrin. (3B) Sodium channel modulators (DDTs) DDT, Methoxychlor.

[0090] (4) Nicotinic acetylcholine receptor (nAChR) competitive modulators Acetamiprid, Clothianidin, Dinotefuran, Imidacloprid, Nitenpyram, Thiacloprid, Thiamethoxam; Nicotine; Sulfoxaflor; Flupyradifurone; Triflumezopyrim. Nithiazine; Dichloromezotiaz, Flupyrimin. (5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators Spinetoram, Spinosad. (6) Glutamate-gated chloride channel (GluCl) allosteric modulators Abamectin, Emamectin, Emamectin-benzoate, Lepimectin, Milbemectin. Doramectin, Eprinomectin, Ivermectin, Moxidectin, Selamectin.

[0091] (7) Juvenile hormone analogues Hydroprene, Kinoprene, Methoprene; Fenoxycarb; Pyriproxifen. Diofenolan, Epophenonane, Triprene. (8) Other nonspecific (multi-site) inhibitors Methyl bromide, alkyl halides; chloropicrin; sodium aluminum fluoride, sulfuryl fluoride; borax, boric acid, disodium octaborate, sodium borate, sodium metaborate; tartar emetic; dazomet, metam, metam sodium, metam potassium. (9) Chordotonal organ TRPV channel modulators Pymetrozine, Pyrifluquinazon; Afidopyropen. (10) Mite growth inhibitor Clofentezine, Diflovidazin, Hexythiazox; Etoxazole.

[0092] (11) Microbial-derived insect midgut membrane disrupting agents Bt subsp. israelensis, Bt subsp. aizawai, Bt subsp. kurstaki, Bt subsp. tenebrionis; Bt crop proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / Cry35Ab1; Bacillus sphaericus. (12) Mitochondrial ATP synthase inhibitors Diafenthiuron; Azocyclotin, Cyhexatin, Fenbutatin-oxide; Propargite; Tetradifon. (13) Oxidative phosphorylation uncouplers that disrupt proton gradients Chlorfenapyr, DNOC (4,6-dinitro-o-cresol), sulfluramid. Binapacryl, Dinobuton, Dinocap. (14) Nicotinic acetylcholine receptor (nAChR) channel blockers Bensultap, Cartap hydrochloride, Thiocyclam, Thiosultap-sodium.

[0093] (15) Chitin biosynthesis inhibitor, type 0 Bistrifluron, Chlorfluazuron, Diflubenzuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron, Noviflumuron, Teflubenzuron, Triflumuron. Fluazuron. (16) Chitin biosynthesis inhibitor, type 1 Buprofezin. (17) Molting inhibitor Cyromazine. (18) Ecdysone receptor agonist Chromafenozide, Halofenozide, Methoxyfenozide, Tebufenozide.

[0094] (19) Octopamine receptor agonists Amitraz. Chlordimeform. (20) Mitochondrial electron transport chain complex III inhibitor Hydramethylnon; Acequinocyl; Fluacrypyrim; Bifenazate. (21) Mitochondrial electron transport complex I inhibitor (METI) Fenazaquin, Fenpyroximate, Pyridaben, Pyrimidifen, Tebufenpyrad, Tolfenpyrad; Rotenone. (22) Voltage-dependent sodium channel blockers Indoxacarb; Metaflumizone. (23) Acetyl-CoA carboxylase inhibitors Spirodiclofen, Spiromesifen, Spirotetramat. Spiropidione. (24) Mitochondrial electron transport chain complex IV inhibitor Aluminum phosphide (Al-phosphide), calcium phosphide (Ca-phosphide), zinc phosphide (Zn-phosphide), phosphine; calcium cyanide (Ca-cyanide), sodium cyanide (Na-cyanide), potassium cyanide (K-cyanide). (25) Mitochondrial electron transport chain complex II inhibitor Cyenopyrafen, Cyflumetofen; Pyflubumide.

[0095] (28) Ryanodine receptor modulators Chlorantraniliprole, Cyantraniliprole, Cyclaniliprole, Flubendiamide. Cyhalodiamide, Tetrachlorantraniliprole, Tetraniliprole. (29) Chord tone organ modulator target region unspecified Flonicamid. (30) GABA-gated chloride channel allosteric modulators Broflanilide, Fluxametamide. Isocycloseram; Afoxolaner, Fluralaner, Lotilaner, Sarolaner.

[0096] (31) Other insecticides and acaricides Azadirachtin, Benzoximate, Bromopropylate, Chinomethionate, Dicofol, Lime sulfur, Mancozeb, Pyridalyl, Sulfur. Acynonapyr, Amidoflumet, Benzomate, Benzpyrimoxan, Chlorobenzilate, Dicyclanil, Fenoxacrim, Fentrifanil, Flometoquin, Flubenzimine, Flufenzine, Fluhexafon, Fluopyram, Metaflumizone, Metoxadiazone, Oxazosulfyl, Tetrasul, Triarathene, Tyclopyrazoflor.

[0097] Specific examples of anthelmintics that can be mixed or used in combination with the pest control agent of the present invention are shown below. (a) Benzimidazoles: fenbendazole, albendazole, triclabendazole, oxibendazole, mebendazole, oxfendazole, perbendazole, flubendazole; febantel, netobimin, thiophanate; thiabendazole, 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: cyclodiene, ryania, clorsulon, metronidazole, demiditraz; piperazine, diethylcarbamazine, dichlorophen, monepantel, tribendimidine, amidantel; thiacetarsamide, melarsamine, arsenamide.

[0098] 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) Inhibitors of nucleic acid synthesis metabolism A1) RNA polymerase I inhibitors Benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, metalaxyl-M; oxadixyl; ofurace. A2) Adenosine deaminase inhibitors Bupirimate, dimethirimol, ethirimol. A3) DNA / RNA biosynthesis inhibitors Hymexazole, octhilinone. A4) DNA topoisomerase type II inhibitors Oxolinic acid.

[0099] (B) Agents acting on the cytoskeleton and motor proteins B1)~B3) Inhibition of β-tubulin polymerization Benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate, thiophanate-methyl, diethofencarb, zoxamide, Ethaboxam. Chlorfenazole, debacarb, trichlamide, zarilamid. B4) Cell division (point of action unknown) Pencycuron. B5) Delocalization of spectrin-like proteins Fluopicolide, fluopimomide. B6) Actin / myosin / fimbrin functions Phenamacril, metrafenone, pyriophenone.

[0100] (C) Respiratory inhibitors C1) Complex I: NADH oxidoreductase Diflumetorim, tolfenpyrad, fenazaquin. C2) Complex II: succinate dehydrogenase benodanil, flutolanil, mepronil; isofetamide; fluopyram; cyclobutrifluram; fenfuram; carboxin, oxycarboxin; thifluzamide; benzovindiflupyr, bixafen, fluipyramine ... Fluindapyr, fluxapyroxad, furametpyr, inpyrfluxam, isopyrazam, penflufen, penthiopyrad, sedaxane; isoflucypram; pydiflumetofen; boscalid; pyraziflumid. Furmecyclox. C3) Complex III: cytochrome bc1 (ubiquinol oxidase) Qo site (cyt b gene) Azoxystrobin, coumoxystrobin, enoxastrobin, flufenoxystrobin, picoxystrobin, pyraoxystrobin; mandestrobin (mandestrobin); pyraclostrobin, pyrametostrobin, triclopyricarb; kresoxim-methyl, trifloxystrobin; dimoxystrobin, fenaminstrobin, metominostrobin, orysastrobin; famoxadone; fluoxastrobin; fenamidone; pyribencarb; methyltetraprole. C4) Complex III: Ubiquinone reductase Qi site cyazofamid; amisulbrom; fenpicoxamid, florylpicoxamid. C5) Uncoupling of oxidative phosphorylation Binapacryl, dinocap, meptyldinocap; fluazinam. C6) Inhibition of oxidative phosphorylation and ATP synthase Triphenyltin acetate, triphenyltin chloride, fentin hydroxide. C7) ATP transport Silthiofam. C8) Complex III: ubiquinone reductase (Qo site, stigmatellin-binding subsite) Ametoctradin.

[0101] (D) Inhibitors of amino acid and protein synthesis D1) Methionine biosynthesis (cgs gene) Cyprodinil, mepanipyrim, pyrimethanil. D2) Protein synthesis (ribosome translation termination stage) Blasticidin S D3), ​​D4) Protein synthesis (ribosome translation initiation stage) Kasugamycin, kasugamycin hydrochloride, streptomycin. D5) Protein synthesis (ribosomal polypeptide elongation step) Oxytetracycline.

[0102] (E) Signal transduction inhibitors E1) Signal transduction (mechanism of action unknown) Quinoxyfen, proquinazid. E2) MAP / histidine kinase (os-2, HOG1) in osmotic signaling Fenpiclonil, fludioxonil. E3) MAP / histidine kinase (os-1, Daf1) in osmotic signaling Chlozolinate, dimethachlone, iprodione, procymidone, vinclozolin.

[0103] (F) Agents that inhibit lipid biosynthesis or transport / cell membrane structure or function F2) Phospholipid biosynthesis, methyltransferase Edifenphos, iprobenfos, pyrazophos; isoprothiolane. F3) Cellular peroxidation Biphenyl, chloroneb, dicloran, quintozene, tecnazene, tolclofos-methyl; etridiazole. F4) Cell membrane permeability, fatty acids Iodocarb, propamocarb, propamocarb hydrochloride, prothiocarb. F8) Ergosterol bond Natamycin. F9) Lipid homeostasis and transport / storage Oxathiapiprolin, fluoxapiprolin.

[0104] (G) Inhibitors of sterol biosynthesis in the plasma membrane G1) C14 demethylase of sterol biosynthesis (erg11 / cyp51) Triforine, pyrifenox, pyrisoxazole, fenarimol, nuarimol, imazalil, oxpoconazole, pefurazoate, prochloraz, triflumizole, azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole Fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, mefentrifluconazole, metconazole, myclobutanil, penconazole, propiconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, and prothioconazole. Fluconazole, furconazole-cis, diniconazole-M. G2) Δ14 reductase and Δ8→Δ7-isomerase (erg24, erg2) in sterol biosynthesis Aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph; fenpropidin, piperalin; spiroxamine. Buthiobate. G3) 3-ketoreductase (erg27) in the C4 demethylation of sterol biosynthesis Fenhexamid; fenpyrazamine. G4) Squalene epoxidase (erg1) of the sterol biosynthesis pathway Pyributicarb; naftifine, terbinafine.

[0105] (H) Inhibitors of cell wall biosynthesis H4) Chitin synthase Polyoxin. Polyoxorim. H5) Cellulose synthase Dimethomorph, flumorph, pyrimorph; Benthiavalicarb, iprovalicarb, valifenalate; mandipropamid.

[0106] (I) Inhibitor of cell wall melanin synthesis I1) Reductases of melanin biosynthesis Fthalide; pyroquilon; tricyclazole. I2) Dehydratase of melanin biosynthesis Carpropamid; diclocymet; fenoxanil. I3) Polyketide synthase in melanin biosynthesis Tolprocarb.

[0107] (P) Agents that induce resistance in host plants P1-P3) Salicylic Acid Signaling Acibenzolar-S-methyl; probenazole; tiadinil, isotianil. P4) Polysaccharide elicitor Laminarin. P5) Anthraquinone elicitor Giant knotweed extract (extract from Reynoutria sachalinensis). P6) Microbial elicitors Bacillus mycoides isolate J; cell walls of Saccharomyces cerevisiae strain LAS117. P7) Phosphonate Fosetyl (fosetyl-Al); phosphorous acid and salts; fosetyl calcium (fosetyl-K), fosetyl sodium (fosetyl-Na). P8) Salicylic acid-related Dichlobentiazox

[0108] (U) Agents with unknown mechanism of action Cymoxanil; tecloftalam; triazoxide; flusulfamide; diclomezine; cyflufenamid; dodine, dodine free base; flutianil; ferimzone; tebufloquin; picarbutrazox; validamycin. bethoxazin, cyprofuram, flumetover, Nitrothal-isopropyl, propamidine. Ipflufenoquin, pyridaclomethyl, pyrapropoyne, aminopyrifen, ipfentrifluconazole, quinofumelin, dipymetitrone.

[0109] (M) Agents exhibiting multisite contact activity Copper (different salts), basic copper sulfate, Bordeaux mixture, copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, cuprous oxide, oxine-copper; sulfur, lime sulfur; amobam, ferbam, mancozeb, maneb, metiram, propineb, thiuram, zinc thiazole Thiazole, zineb, ziram; captan, captafol, folpet; chlorothalonil; dichlofluanid, tolylfluanid; guazatine, guazatine acetates, iminoctadine, iminoctadine acetate, iminoctadine triacetate, iminoctadine tribesilate; anilazine; dithianon; chinomethionate; fluoroimide; methasulfocarb. Dazomet, cufraneb, mancopper, polycarbamate.

[0110] (BM01) Biological pesticides with multiple modes of action / biologically derived pesticides Extract from the cotyledons of lupine plantlets; extract from Swinglea glutinosa; extract from Melaleuca alternifolia (tea tree oil); plant oils (mixtures): eugenol, geraniol, thymol.

[0111] (BM02) Multi-mode biopesticides / biological pesticides Trichoderma atroviride strain I-1237, Trichoderma atroviride strain LU132, Trichoderma atroviride strain SC1, Trichoderma atroviride strain SKT-1, Trichoderma atroviride strain 77B; Trichoderma asperellum strain T34, Trichoderma asperellum strain kd; Trichoderma harzianum strain T-22; Trichoderma virens strain G-41; Gliocladium catenulatum strain J1446; Clonostachys rosea strain CR-7; Coniothyrium minitans strain CON / M / 91-08; Talaromyces flavus strain SAY-Y-94-01; Saccharomyces cerevisiae strain LAS02; Bacillus amyloliquefaciens strain QST713, Bacillus amyloliquefaciens strain FZB24, Bacillus amyloliquefaciens strain MBI600, Bacillus amyloliquefaciens strain D747, Bacillus amyloliquefaciens strain F727, Bacillus amyloliquefaciens strain AT-332; Bacillus subtilis strain AFS032321, Bacillus subtilis strain Y1336, Bacillus subtilis strain HAI-0404; Pseudomonas chlororaphis strain AFS009; Streptomyces griseovirides strain K61; Streptomyces lydicus strain WYEC108. (NC) Unclassified ingredients Mineral oils, organic oils, inorganic salts, material of biological origin.

[0112] 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. Abscisic acid, kinetin, benzylaminopurine, 1,3-diphenylurea, forchlorfenuron, thidiazuron, chlorfenuron, dihydrozeatin, gibberellin A, gibberellin A4, gibberellin A7, gibberellin A3, 1-methylcyclopropane, N-acetylaminoethoxyvinylglycine (also known as abiglycine), aminooxyacetic acid, silver nitrate, cobalt chloride, IAA, 4-CPA, cloprop, 2,4-D, MCPB, indole-3-butyric acid, dichlorprop, fu Thiol, 1-naphthylacetamide, ethychlozate, cloxifonac, maleic hydrazide, 2,3,5-triiodobenzoic acid, salicylic acid, methyl salicylate, (-)-jasmonic acid, methyl jasmonate, (+)-strigol, (+)-deoxystrigol, (+)-orobanchol, (+)-sorgolactone, 4-oxo-4-(2-phenylethyl)aminobutyric acid; ethephon, chlormequat, mepiquat chloride, benzyladenine, 5-aminolevulinic acid.

[0113] [Ectoparasite control agent] The ectoparasite-controlling agent of the present invention contains at least one compound selected from the compounds of the present invention as an active ingredient. The amount of the compound of the present invention contained in the ectoparasite-controlling agent of the present invention is not particularly limited as long as it exhibits an ectoparasite-controlling effect.

[0114] 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.

[0115] The ectoparasite-controlling agent of the present invention can be administered by known veterinary methods (topical, oral, parenteral, or subcutaneous administration). These methods include oral administration to animals using tablets, capsules, or by incorporating the agent into feed; administration to animals using immersion solutions, suppositories, or injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.); local administration of oily or aqueous liquids using sprays, pour-on, spot-on, etc.; kneading the ectoparasite-controlling agent into a resin, molding the kneaded product into a suitable shape such as a collar or ear tag, and then attaching the kneaded product to the animal for local administration; Examples include:

[0116] 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.

[0117] (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. (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. (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. (4) Hemiptera. (5) Pests of the Diptera order: 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.

[0118] [Internal parasite control or extermination agent] The agent for controlling or eliminating endoparasites of the present invention contains at least one compound selected from the compounds of the present invention as an active ingredient. The amount of the compound of the present invention contained in the agent for controlling or eliminating endoparasites of the present invention is not particularly limited as long as it shows an effect of controlling endoparasites.

[0119] 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.

[0120] 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.

[0121] (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.

[0122] (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.

[0123] (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.

[0124] (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).

[0125] (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.

[0126] (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).

[0127] (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).

[0128] (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.

[0129] (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.

[0130] (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.

[0131] [Control agents for other pests] The compound of the present invention is 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.).

[0132] 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.

[0133] (2) Other pests Cockroaches (Blattodea), termites (termite), spiders (Araneae), centipedes (cetipede), millipedes (millipede), crustaceans (crustacea), bedbugs (Cimex lectularius).

[0134] [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 indicate parts by weight. The formulations for agricultural and horticultural use and for paddy rice are shown below.

[0135] (Formulation 1: Wettable powder) 40 parts of the 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. (Formulation 2: emulsion) 30 parts of the 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. (Formulation 3: Granules) Five parts of the 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. (Formulation 4: Granules) Five parts of the 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. (Formulation 5: Suspension) 10 parts of the 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 becomes 3 microns or less, to obtain a suspension containing 10% of the active ingredient.

[0136] The formulations for external parasite control agents or internal parasite control or extermination agents are shown below. (Formulation 6: Granules) 5 parts of the 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. (Formulation 7: Injection) 0.1 to 1 part of the 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. (Formulation 8: pour-on) A pour-on agent is obtained by uniformly mixing 5 parts of the compound of the present invention, 10 parts of myristate ester, and 85 parts of isopropanol. (Formulation 9: Spot-on) A spot-on preparation is obtained by uniformly mixing 10 to 15 parts of the compound of the present invention, 10 parts of palmitic acid ester, and 75 to 80 parts of isopropanol. (Formulation 10: Spray) A spray formulation is obtained by uniformly mixing 1 part of the compound of the present invention, 10 parts of propylene glycol, and 89 parts of isopropanol.

[0137] Next, the present invention will be described in more detail with reference to examples, but the present invention is not limited to the following examples.

[0138] Example 1 (Z)-2-(3-(5-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-1-methyl-1H-imidazol-2-yl)-4-(ethylsulfonyl)-1H-pyrazol-1-yl)pyrimidine (Compound Number A-17) was synthesized through the following steps.

[0139] (Process 1) Synthesis of 1-(5-((Z)-2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-1-methyl-1H-imidazol-2-yl)-3-(dimethylamino)-2-(ethylsulfonyl)prop-2-en-1-one

[0140] TIFF2025134093000011.tif30146 (Z)-1(5-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-1-methyl-1H-imidazol-2-yl)-2-(ethylsulfonyl)ethan-1-one (0.38 g) was dissolved in tetrahydrofuran (5 ml) and stirred at room temperature. N,N-dimethylformamide dimethyl acetal (0.38 g) was added to the solution, and the mixture was stirred under reflux for 4 hours. The resulting solution was concentrated under reduced pressure, and the concentrate was purified by silica gel column chromatography to obtain 0.39 g of the target product (yield 97%). The obtained target 1 The H-NMR is shown below. 1 H-NMR(400 MHz, CDCl3): δ 7.91 (s, 1H), 7.83 (s, 1H), 7.13 (s, 1H), 3.85 (s, 3H), 3.49 (q, 2H), 3.33 (s, 3H), 2.80 (s, 3H), 1.32 (t, 3H).

[0141] (Process 2) Synthesis of (Z)-3-(5-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-1-methyl-1H-imidazol-2-yl)-4-(ethylsulfonyl)-1H-pyrazole

[0142] TIFF2025134093000012.tif37163

[0143] 1-(5-((Z)-2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-1-methyl-1H-imidazol-2-yl)-3-(dimethylamino)-2-(ethylsulfonyl)prop-2-en-1-one (1.2 g) was dissolved in acetic acid (5 ml) and stirred at room temperature. To this was added hydrazine monohydrate (0.17 g), and the mixture was stirred at room temperature for 2 hours. The resulting solution was concentrated under reduced pressure, and the resulting concentrate was poured into a saturated aqueous solution of sodium bicarbonate and extracted with dichloromethane. The resulting organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting concentrate was purified by silica gel column chromatography to obtain 0.040 g (yield 3%) of the target product. The obtained target 1 The H-NMR is shown below. 1H-NMR (400 MHz, CDCl3): δ 8.22 (s, 1H), 8.08 (s, 1H), 7.15 (s, 1H), 3.84 (s, 3H), 3.80 (1q 2H), 1.33 (t, 3H).

[0144] (Step 3) Synthesis of (Z)-2-(3-(5-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-1-methyl-1H-imidazol-2-yl)-4-(ethylsulfonyl)-1H-pyrazol-1-yl)pyrimidine

[0145] TIFF2025134093000013.tif41166

[0146] (Z)-3-(5-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-1-methyl-1H-imidazol-2-yl)-4-(ethylsulfonyl)-1H-pyrazole (0.040 g) was dissolved in N,N-dimethylformamide (2 ml) and stirred at room temperature. 2-Chloropyrimidine (0.023 g) and potassium carbonate (0.040 g) were added to the solution, and the mixture was stirred at 50°C for 1 hour. The resulting solution was poured into a saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The resulting organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting concentrate was purified by silica gel column chromatography to obtain 0.013 g of the target product (yield 26%). The obtained target 1 The H-NMR is shown below. 1H-NMR(400 MHz, CDCl3): δ 9.26 (s, 1H), 8.86 (d, 2H), 8.10 (s, 1H), 7.41 (t, 1H), 7.16 (s, 1H), 3.87 (s, 3H), 3.83 (q, 2H), 1.40 (t, 3H).

[0147] The compounds of the present invention were synthesized in the same manner as in Example 1. Some of them are shown in Table 1. The melting point (mp) is listed in the physical properties column. NMR data is listed for amorphous compounds. *

[0148] [Table 1]

[0149] TIFF2025134093000015.tif222138

[0150] TIFF2025134093000016.tif222138

[0151] TIFF2025134093000017.tif99138

[0152] Compounds with AMORPHOUS properties are 1 The product was analyzed by H-NMR. Compound No. A-7: 1 H NMR (400MHz, CDCl3) δ 7.46 - 7.39 (m, 2H), 7.28 (d, 2H), 7.23 (s, 1H), 3.73 (s, 3H), 3.03 (q, 2H), 1.56 (s, 18H), 1.35 (t, 3H).

[0153] [Biological Testing] The usefulness of the compounds of the present invention as active ingredients for pesticides and ectoparasite control agents will be demonstrated in the following test examples, in which "parts" are by weight.

[0154] (Preparation of test emulsion) 5 parts of the compound of the present invention, 93.6 parts of dimethylformamide, and 1.4 parts of polyoxyethylene alkylaryl ether were mixed to obtain an emulsifiable concentrate (I) containing 5% of the active ingredient. For comparison, 98.5 parts of dimethylformamide and 1.5 parts of polyoxyethylene alkylaryl ether were mixed to obtain an emulsifiable concentrate (II).

[0155] The insecticidal rate was calculated using the following formula: Insecticidal rate (%) = (number of dead insects / number of test insects) x 100 The control rate was calculated using the following formula: Control rate (%) = {1 - (number of larvae in the compound-treated area / number of larvae in the control area)} x 100

[0156] (Test Example 1) Efficacy test against diamondback moth Emulsifiable concentrate (I) was diluted with water to a concentration of the compound of the present invention of 125 ppm. Cabbage leaves were immersed in the diluted solution for 30 seconds. The cabbage leaves were placed in a petri dish. Five second-instar diamondback moth larvae were released into the cabbage leaves. The petri dish was placed in a thermostatic chamber at a temperature of 25°C and a humidity of 60%. Three days after release, the survival rate was determined and the insect mortality rate was calculated. This procedure was repeated twice.

[0157] Compounds A-1, A-2, A-6, A-8, A-10, A-14 and A-16 were tested for efficacy against diamondback moth. All compounds showed an insecticidal rate of 80% or more against diamondback moth.

[0158] (Test Example 2) Efficacy test against oriental fruit moth Apple fruits were placed in a case. The case was placed in a temperature-controlled room at a temperature of 25°C and humidity of 60%. Ten adult pear fruit moths were released into the case, and two days later, the ten adults were removed. Eggs were laid on the fruit. The number of eggs was counted. Emulsion (I) was diluted with water to a concentration of the compound of the present invention of 125 ppm. The diluted solution was sprayed on the apple fruits. Twelve days after spraying, the number of eggs and larvae was counted for survival. The insecticidal rate was calculated from the number of dead eggs and larvae relative to the number of eggs laid. This was repeated twice.

[0159] The compound No. A-1 was tested for efficacy against the oriental fruit moth, and showed an insecticidal rate of 80% or more against the oriental fruit moth.

[0160] (Test Example 3) Efficacy test against striped flea beetles Emulsifiable concentrate (I) was diluted with water to a concentration of 125 ppm to prepare a test solution. The test solution was sprayed onto bok choy seedlings (at the seventh true leaf stage) planted in 3-inch pots. The bok choy seedlings were air-dried and then placed in plastic cups. Ten adult striped flea beetles were released into the cups. The cups were stored in a constant temperature room at 25°C and 65% humidity, and after 7 days from release, the adult beetles were counted as dead or alive, and the insecticidal rate was calculated. This was repeated twice.

[0161] Compound A-16 was tested for efficacy against adult flea beetles, and showed an insecticidal rate of 80% or more against adult flea beetles.

[0162] (Test Example 4) Efficacy test against cotton aphids Cucumber seeds were sown in 3-inch pots. 10 days after germination, adult female cotton aphids were released onto the cucumbers. The next day, the adult females were removed, leaving only the first-instar nymphs that had been laid. Emulsifiable concentrate (I) was diluted with water to a concentration of 125 ppm of the compound of the present invention. This diluted solution was sprayed on the cucumbers. The cucumbers were then stored in a thermostatic chamber at a temperature of 25°C and a humidity of 60%. After 5 days, the survival rate was assessed and the insecticidal rate was calculated. This was repeated twice.

[0163] Compound No. A-16 was tested for efficacy against adult cotton aphids, and showed an insecticidal rate of 80% or more against adult cotton aphids.

[0164] (Test Example 5) Efficacy test against brown planthoppers Emulsifiable concentrate (I) was diluted with water to a concentration of the compound of the present invention of 125 ppm. Rice seedlings were immersed in the diluted solution for 30 seconds and air-dried. They were placed in a plastic case, and five second-instar larvae of the brown planthopper were released into it. The case was stored in a thermostatic chamber at 25°C and 65% humidity. Seven days after release, the live or dead insects were counted, and the insecticidal rate was calculated. This procedure was repeated twice.

[0165] Compounds A-1 and A-16 were tested for efficacy against brown planthoppers, and both compounds showed insecticidal rates of 80% or more.

[0166] (Test Example 6) Efficacy test against southern melon thrips (125 ppm) Ten adult melon thrips were released onto cucumber seedlings. Emulsion (I) was diluted with water to a concentration of the compound of the present invention of 125 ppm to obtain a test solution. Emulsion (II) was diluted with water at the same dilution as emulsion (I) to obtain a control solution. The test solution or control solution was sprayed onto cucumber seedlings and air-dried. Two days after spraying, the adult insects were removed. Eggs were laid on the cucumber seedlings. Seven days after spraying, the number of parasitic larvae that had hatched from the eggs was counted. The control rate was calculated. This was repeated twice.

[0167] Compound A-16 was tested for efficacy against Thrips palmi, and the control rate was 80% or more.

[0168] (Test Example 7) Efficacy test against cat fleas The compound of the present invention was dissolved in isopropanol to prepare a solution with a concentration of 20 ppm. 100 μL of this solution was applied to the inner surface of the bottom of a glass vial (φ330 mm) and air-dried to form a thin film of the compound of the present invention. Four adult cat fleas (Ctenocephalides felis) (male and female mixed) were released into the vial. The vial was then capped and placed in a thermostatic chamber at 25°C. Four days after release, the cat fleas were counted for survival and the mortality rate was calculated. This was repeated twice.

[0169] Compounds A-1, A-16, and A-17 were tested for efficacy against cat fleas, and all of the compounds showed an insecticidal rate of 80% or more against cat fleas.

[0170] (Test Example 7) Efficacy test against Haemaphysalis longicornis The compound of the present invention was dissolved in isopropanol to prepare a solution with a concentration of 20 ppm. 20 μL of this solution was applied to the inner surface of the bottom of a glass test tube (φ12 mm) and air-dried to form a thin film of the compound of the present invention. Four nymphs of the Haemophysalis longicornis tick were released into the test tube. The tube was then covered and placed in a thermostatic chamber at 25°C. Four days after release, the mites were counted for survival and death, and the mortality rate was calculated. This process was repeated twice.

[0171] Compound No. A-17 was tested for efficacy against Haemaphysalis longicornis. All compounds showed an insecticidal rate of 80% or more against Haemaphysalis longicornis.

[0172] Since all of the imidazolyl azole compounds randomly selected from the imidazolyl azole compounds of the present invention exhibit the above-mentioned effects, it can be understood that the imidazolyl azole compounds of the present invention, including compounds not listed as examples, are compounds that have pest control effects, particularly acaricidal and insecticidal effects, etc. It can also be understood that they are compounds that are effective against parasites that are harmful to humans and animals, such as ectoparasites.

Claims

1. A compound represented by formula (I) or a salt thereof: A-B (I) [In formula (I), A is a group represented by formula (A1) or a group represented by formula (A2), In formulas (A1) and (A2), * indicates the binding site with B, R １ is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, or a substituted or unsubstituted phenyl group, R ２ is a substituted or unsubstituted C1-6 alkyl group, R ３ is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, an amino group, a cyano group, or a halogeno group, In formula (I), B is a group represented by formula (B1) or a group represented by formula (B2), In formulas (B1) and (B2), * indicates the binding site with A, R ４ represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5-10 membered heterocyclyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aminocarbonyl group, -C(=N-OR ａ ) R ｂ a nitro group, a cyano group, or a halogeno group; R ａ is a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group, R ｂ is a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group, R ５ is a substituted or unsubstituted C1-6 alkyl group or a substituted or unsubstituted C3-6 cycloalkyl group, n represents the number of O and is 0, 1 or 2.

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

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

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

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

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