Heteroarylpyrimidine compound and pest control agent

Abstract

To provide a novel heteroarylpyrimidine compound that is excellent in insecticidal and / or acaricidal activity and safety and can be industrially advantageously synthesized.SOLUTION: Provided is a compound represented by formula (I) or a salt thereof. [In the formula: R1 is a C2-6 alkenyl group, a C2-6 alkynyl group, or the like; R2 is H, a C1-6 alkyl group, a halogeno group, or the like; R3 is a C1-6 alkyl group, or the like; X1 is H, a C1-6 alkyl group, a hydroxy group, a C1-6 alkoxy group, a C3-6 cycloalkyl group, a phenyl group, a halogeno group, or the like; X2 is H, a C1-6 alkyl group, or the like; Y is a group represented by -S(=O)n- or -S(=O)(=NRN)-; n is any integer from 0 to 2; and RN is H, a C1-6 alkyl group, or the like.]SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a heteroarylpyrimidine compound and a pesticide. More specifically, the present invention relates to a heteroarylpyrimidine compound that has excellent insecticidal and / or acaricidal activity, is safe, and can be synthesized industrially in an advantageous manner, and a pesticide containing the compound as an active ingredient. [Background technology]

[0002] Various compounds with insecticidal and acaricidal activity have been proposed. In order for such compounds to be practically used as pesticides, they must not only be sufficiently effective, but also unlikely to develop drug resistance, not cause plant damage or soil contamination, and have low toxicity to livestock and fish.

[0003] Incidentally, Patent Document 1 discloses a compound represented by formula (A) and the like. TIFF2025026809000001.tif48150

[0004] Patent Document 2 discloses a compound represented by formula (B) and the like. TIFF2025026809000002.tif48150 [Prior art documents] [Patent documents]

[0005] [Patent Document 1] WO 2017 / 104741 A1 [Patent Document 2] WO 2020 / 071304 A1 [Non-patent literature]

[0006] [Non-Patent Document 1] "Graphical representation of stereochemical configuration", Pure and Applied Chemistry 78, 1897-1970, 2006 IUPAC Summary of the Invention [Problem to be solved by the invention]

[0007] The object of the present invention is to provide a heteroarylpyrimidine compound that has excellent pest control activity, particularly excellent insecticidal and / or acaricidal activity, is safe, and can be synthesized industrially advantageously. Another object of the present invention is to provide a pest control agent, an insecticide or acaricide, an external parasite control agent, or an internal parasite control or extermination agent, which contains the heteroarylpyrimidine 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. TIFF2025026809000003.tif50150 [In formula (I), R 1 is a substituted or unsubstituted C2-6 alkenyl group, or a substituted or unsubstituted C2-6 alkynyl group, R 2 is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a halogeno group, R 3 is a substituted or unsubstituted C1-6 alkyl group, X 1 and X 2each independently 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 hydroxyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted A C1-6 alkylsulfonyl 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 phenoxy group, a substituted or unsubstituted naphthoxy group, a substituted or unsubstituted 5-10 membered heterocyclyloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aminocarbonyl group, a nitro group, a cyano group, a halogeno group or -C(R c )=N-OR d is a group represented by R c is a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group, R d is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, or a C2-6 alkynyl group, Y is -S(=O) n -, or -S(=O)(=NR N )-, n represents the number of =O and is an integer of 0 to 2; R Nis 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 C1-6 alkylsulfonyl 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 heteroaryl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aminocarbonyl group, a nitro group, or a cyano group.]

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

[0010] The heteroarylpyrimidine compound of the present invention can control pests that are problematic in agricultural crops and hygiene.The heteroarylpyrimidine compound of the present invention can effectively control agricultural pests and mites at a lower concentration.The heteroarylpyrimidine compound of the present invention can also effectively control external and internal parasites that harm humans and livestock. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0011] The heteroarylpyrimidine 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).

[0012] TIFF2025026809000004.tif51150

[0013] In the present invention, the term "unsubstituted" means that only the group serving as the mother nucleus is present. When there is no description of "substituted" and only the name of the group serving as the mother nucleus is described, 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. Thus, a "substituent" is another group bonded to the core group. The number of substituents may be one or more. The two or more substituents may be the same or different. Terms such as "C1-6" indicate that the number of carbon atoms in the parent group is 1 to 6. This number of carbon atoms does not include the number of carbon atoms in the substituent. For example, a butyl group having an ethoxy group as a substituent is classified as a C2 alkoxy C4 alkyl group. The "substituents" are not particularly limited as long as they are chemically permissible and have the effect of the present invention.

[0014] Examples of groups which 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 groups; C2-6 alkenyl groups such as vinyl group, 1-propenyl group, 2-propenyl group (allyl group), 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, and 2-methyl-2-propenyl group; C2-6 alkynyl groups, such as an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, or a 1-methyl-2-propynyl group;

[0015] C3-6 cycloalkyl groups such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group; 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;

[0016] Hydroxyl; C1-6 alkoxy groups, such as a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an s-butoxy group, an i-butoxy group, or a t-butoxy group; C2-6 alkenyloxy groups such as a vinyloxy group, an allyloxy group, a propenyloxy group, or a butenyloxy group; 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;

[0017] Formyl group; C1-6 alkylcarbonyl groups such as acetyl and propionyl groups; Formyloxy group; C1-6 alkylcarbonyloxy groups such as acetyloxy and propionyloxy; 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, or 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, or a t-butoxycarbonyloxy group; Carboxyl group;

[0018] 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, or a 5-bromo-2-pentynyl group; C1-6 haloalkoxy groups such as a trifluoromethoxy group, a 2-chloro-n-propoxy group, or a 2,3-dichlorobutoxy group; C2-6 haloalkenyloxy groups, such as a 2-chloropropenyloxy group or a 3-bromobutenyloxy group; C1-6 haloalkylcarbonyl groups such as a chloroacetyl group, a trifluoroacetyl group, or a trichloroacetyl group;

[0019] Amino group; C1-6 alkyl-substituted amino groups such as methylamino, dimethylamino, and diethylamino groups; Anilino group, naphthylamino group; phenyl C1-6 alkylamino groups such as benzylamino and phenethylamino groups; Formylamino group; C1-6 alkylcarbonylamino groups, such as an acetylamino group, a propanoylamino group, a butyrylamino group, or an i-propylcarbonylamino group; 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 group such as an iminomethyl group, a (1-imino)ethyl group, or 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;

[0020] 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, or 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;

[0021] 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;

[0022] C1-6 alkylsulfonyl groups such as a methylsulfonyl group, an ethylsulfonyl group, or a t-butylsulfonyl group; C1-6 haloalkylsulfonyl groups, such as a trifluoromethylsulfonyl group or 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 or a 2,2,2-trifluoroethylsulfonyloxy group;

[0023] Tri-C1-6 alkyl-substituted silyl groups, such as trimethylsilyl group, triethylsilyl group, and t-butyldimethylsilyl group; Triphenylsilyl group; Cyano group; nitro group.

[0024] In addition, 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.

[0025] The above-mentioned "3- to 6-membered heterocyclyl group" includes 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 a monocyclic or polycyclic ring. As for the polycyclic heterocyclyl group, as long as at least one ring is a heterocyclic ring, the remaining rings may be either a saturated alicyclic ring, an unsaturated alicyclic ring, or an aromatic ring. Examples of the "3- to 6-membered heterocyclyl group" include a 3- to 6-membered saturated heterocyclyl group, a 5- to 6-membered heteroaryl group, and a 5- to 6-membered partially unsaturated heterocyclyl group.

[0026] 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.

[0027] 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.

[0028] R in formula (I) 1 is a substituted or unsubstituted C2-6 alkenyl group, or a substituted or unsubstituted C2-6 alkynyl group.

[0029] R 1Examples of the C2-6 alkenyl group in the formula (I) 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. R 1 Examples of the C2-6 alkynyl group in the formula (I) 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.

[0030] R 1 In the above, examples of the substituent on the "C2-6 alkenyl group" or "C2-6 alkynyl group" include halogeno groups such as fluoro, chloro, bromo, and iodo groups; hydroxyl groups; C1-6 alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy, and t-butoxy groups; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy, 2,3-dichlorobutoxy, and trifluoromethoxy groups; phenyl groups; phenyl groups substituted with halogeno groups, C1-6 haloalkyl groups, or C1-6 haloalkoxy groups, such as 4-chlorophenyl, 4-trifluoromethylphenyl, and 4-trifluoromethoxyphenyl groups; or cyano groups. Of these, halogeno groups are preferred. Examples of the halogeno-substituted C2-6 alkenyl group include C2-6 haloalkenyl groups such as a 2,3,3,3-tetrafluoro-1-propenyl group, a 3,3,3-trifluoro-1-propenyl group, a 2-chloro-3,3,3-trifluoro-1-propenyl group, a 2-bromo-3,3,3-trifluoro-1-propenyl group, a 3,3,3-trifluoro-2-trifluoromethyl-1-propenyl group, a 3,3,4,4,4-pentafluoro-1-butenyl group, a 2,3,3,4,4,4-hexafluoro-1-butenyl group, and a 2-chloro-3,3,4,4,4-pentafluoro-1-butenyl group. Examples of the halogeno-substituted C2-6 alkynyl group include C2-6 haloalkynyl groups such as 3,3,3-trifluoro-1-propynyl group.

[0031] [R 2 〕 R in formula (I) 2 is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a halogeno group. R in formula (I) 3 is a substituted or unsubstituted C1 to C6 alkyl group.

[0032] R 2 Examples of the "halogeno group" in the above formula include a fluoro group, a chloro group, a bromo group, and an iodo group. R 2 and R 3 The "C1-6 alkyl group" in R may be a straight chain or a branched chain. 2 and R 3 Examples of the "C1-6 alkyl group" in the above formula 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, an t-butyl group, an i-pentyl group, a neopentyl group, a 2-methylbutyl group, and an i-hexyl group.

[0033] R 2 and R 3 As the substituent on the "C1-6 alkyl 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, 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 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; 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.

[0034] X in formula (I) 1 and X 2 each independently 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 hydroxyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted A C1-6 alkylsulfonyl 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 phenoxy group, a substituted or unsubstituted naphthoxy group, a substituted or unsubstituted 5-10 membered heterocyclyloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aminocarbonyl group, a nitro group, a cyano group, a halogeno group or -C(R c )=N-OR d It is a group represented by the following formula:

[0035] X 1Examples of the "halogeno group" in the above formula include a fluoro group, a chloro group, a bromo group, and an iodo group.

[0036] X 1 and X 2 The "C1-6 alkyl group" in X may be a straight chain or a branched chain. 1 Examples of the "C1-6 alkyl group" in the above formula 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, an t-butyl group, an i-pentyl group, a neopentyl group, a 2-methylbutyl group, and an i-hexyl group.

[0037] X 1 and X 2 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.

[0038] X 1 and X 2 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.

[0039] X 1 and X 2Examples of the "C1-6 alkoxy group" in the above formula include a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an s-butoxy group, an i-butoxy group, and a t-butoxy group.

[0040] X 1 and X 2 Examples of the "C1-6 alkylcarbonyl group" in the above formula include an acetyl group, a propionyl group, an n-propylcarbonyl group, an i-propylcarbonyl group, an n-butylcarbonyl group, and a t-butylcarbonyl group.

[0041] X 1 and X 2 Examples of the "C1-6 alkoxycarbonyl group" in the above formula include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, an n-butoxycarbonyl group, and a t-butoxycarbonyl group.

[0042] X 1 and X 2 Examples of the "C1-6 alkylthio group" in the above formula include a methylthio group, an ethylthio group, an n-propylthio group, an n-butylthio group, an n-pentylthio group, an n-hexylthio group, an i-propylthio group, and an i-butylthio group.

[0043] X 1 and X 2 Examples of the "C1-6 alkylsulfinyl group" in the above formula include a methylsulfinyl group, an ethylsulfinyl group, and a t-butylsulfinyl group.

[0044] X 1 and X 2 Examples of the "C1-6 alkylsulfonyl group" in the above formula include a methylsulfonyl group, an ethylsulfonyl group, and a t-butylsulfonyl group.

[0045] X 1 and X 2In the above, examples of the substituent on the "C1-6 alkyl group", "C2-6 alkenyl group", "C2-6 alkynyl group", "C1-6 alkoxy group", "C1-6 alkylcarbonyl group", "C1-6 alkoxycarbonyl group", "C1-6 alkylthio group", "C1-6 alkylsulfinyl group", or "C1-6 alkylsulfonyl 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, 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 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; 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] X 1 and X 2 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] X 1 and X 2 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 atoms, oxygen atoms, 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 the 5- to 10-membered partially unsaturated heterocyclyl group include 5-membered partially unsaturated heterocyclyl groups such as a pyrrolinyl group, a dihydrofuranyl group, an imidazolinyl group, a pyrazolinyl group, an oxazolinyl group, and an isoxazolinyl group; 6-membered partially unsaturated heterocyclyl groups such as a dihydropyranyl group; 9-membered partially unsaturated heterocyclyl groups such as an indolinyl group, an isoindolinyl group, a 2,3-dihydrobenzofuranyl group, and a 1,3-dihydrobenzofuranyl group; and 10-membered partially unsaturated heterocyclyl groups such as a 1,2,3,4-tetrahydroquinolinyl group.

[0050] X 1 and X 2 Examples of the "5- to 10-membered heterocyclyloxy group" in the above formula include a pyridyloxy group, a pyrimidyloxy group, a piperidyloxy group, a pyrrolinyloxy group, and a dihydrofuranyloxy group.

[0051] X 1 and X 2 In the above, examples of the substituents on the "C3-6 cycloalkyl group", "phenyl group", "naphthyl group", "5- to 10-membered heterocyclyl group", "phenoxy group", "naphthoxy group", or "5- to 10-membered heterocyclyloxy 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, 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 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; 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.

[0052] X 1 and X 2 The "substituted or unsubstituted amino group" in a R b " X 1 and X 2 The "substituted or unsubstituted aminocarbonyl group" in a R b " is a group represented by the formula: a and R b 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.

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

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

[0055] R a and R b 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 c and R d The "C1-6 alkyl group", "C1-6 alkylcarbonyl group", and "substituted or unsubstituted aminocarbonyl group" in a and R b The same examples as those exemplified above can be mentioned.

[0056] X 1 and X 2 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.

[0057] X 1 and X 2 Examples of the "substituted or unsubstituted aminocarbonyl group" in the above formula include a methylaminocarbonyl group, an ethylaminocarbonyl group, a dimethylaminocarbonyl group, and the like.

[0058] R c is a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group. R d is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, or a C2-6 alkynyl group. R c and R d The C1-6 alkyl group in X 1 and X 2 The same examples as those given in the above can be mentioned. R d The C2-6 alkenyl group and the C2-6 alkynyl group in X 1 and X 2 The same examples as those exemplified above can be mentioned. X 1 and X 2 In -C(R c )=N-OR d The group represented by the following formula (1) exhibits cis-trans isomerism due to the double bond. The compound of the present invention includes a compound consisting of any one of such isomers or a compound consisting of two or more such isomers (mixture).

[0059] X 2 is preferably a hydrogen atom.

[0060] In formula (I), Y is -S(=O)n -, or -S(=O)(=NR N )- is a group represented by the formula: n represents the number of =O and is an integer of 0 to 2. R N is 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 C1-6 alkylsulfonyl 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 heteroaryl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aminocarbonyl group, a nitro group, or a cyano group.

[0061] R N The "C1-6 alkyl group" in R may be a straight chain or a branched chain. N Examples of the "C1-6 alkyl group" in the above formula 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, an t-butyl group, an i-pentyl group, a neopentyl group, a 2-methylbutyl group, and an i-hexyl group.

[0062] R N 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.

[0063] R NExamples 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.

[0064] R N Examples of the "C1-6 alkylcarbonyl group" in the above formula include an acetyl group, a propionyl group, an n-propylcarbonyl group, an i-propylcarbonyl group, an n-butylcarbonyl group, and a t-butylcarbonyl group.

[0065] R N Examples of the "C1-6 alkoxycarbonyl group" in the above formula include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, an n-butoxycarbonyl group, and a t-butoxycarbonyl group.

[0066] R N Examples of the "C1-6 alkylsulfonyl group" in the above formula include a methylsulfonyl group, an ethylsulfonyl group, and a t-butylsulfonyl group.

[0067] R N In the above, examples of the substituent on the "C1-6 alkyl group", "C2-6 alkenyl group", "C2-6 alkynyl group", "C1-6 alkylcarbonyl group", "C1-6 alkoxycarbonyl group", or "C1-6 alkylsulfonyl 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, 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 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; 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.

[0068] R N 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.

[0069] R N The "5- to 10-membered heteroaryl group" in the above is an aromatic group containing 1 to 4 heteroatoms selected from the group consisting of nitrogen atoms, oxygen atoms, and sulfur atoms as ring-constituting atoms. 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.

[0070] R N In the above, the substituents on the "C3-6 cycloalkyl group", "phenyl group", "naphthyl group", or "5- to 10-membered heteroaryl group" are: 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, 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 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; 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.

[0071] R N The "substituted or unsubstituted amino group" in a1 R b1 " R N The "substituted or unsubstituted aminocarbonyl group" in a1 R b1 " is a group represented by the formula: a1 and R b1may 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.

[0072] R a1 and R b1 The "C1-6 alkyl group" in N The same examples as those exemplified above can be mentioned.

[0073] R a1 and R b1 Examples of the "C1-6 alkylcarbonyl group" in the above formula include an acetyl group and a propionyl group.

[0074] R a1 and R b1 The "substituted or unsubstituted aminocarbonyl group" in c1 R d1 " is a group represented by the formula: c1 and R d1 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 c1 and R d1 The "C1-6 alkyl group", "C1-6 alkylcarbonyl group", and "substituted or unsubstituted aminocarbonyl group" in a1 and R b1 The same examples as those exemplified above can be mentioned.

[0075] R N 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.

[0076] R NExamples of the "substituted or unsubstituted aminocarbonyl group" in the above formula include a methylaminocarbonyl group, an ethylaminocarbonyl group, a dimethylaminocarbonyl group, and the like.

[0077] The salt of compound (I) is not particularly limited as long as it is an agriculturally and horticulturally acceptable salt.The salt of compound (I) can be, for example, the salt of inorganic acid such as hydrochloric acid, sulfuric acid, etc.; the salt of organic acid such as acetic acid, lactic acid, etc.; the salt of alkali metal such as lithium, sodium, potassium, etc.; the salt of alkaline earth metal such as calcium, magnesium, etc.; the salt of transition metal such as iron, copper, etc.; ammonia; the salt of organic base such as triethylamine, tributylamine, pyridine, hydrazine, etc.

[0078] 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. In addition, a salt of compound (I) can be obtained from compound (I) by a known method.

[0079] The heteroarylpyrimidine compound of the present invention (hereinafter referred to as "the compound of the present invention") has excellent control effects against various agricultural pests and harmful organisms such as mites that affect plant growth. In addition, the compound of the present invention is highly safe because it has little phytotoxicity to crops and low toxicity to fish and warm-blooded animals, and is therefore useful as an active ingredient of insecticides or acaricides. Furthermore, in recent years, many pests, such as diamondback moths, planthoppers, leafhoppers, and aphids, have developed resistance to various existing pesticides, causing problems in which the effectiveness of these pesticides is insufficient, and pesticides that are effective against resistant pests are desired. The compound of the present invention shows excellent control effects not only against susceptible pests, but also against various resistant pests and even against mites resistant to acaricides.

[0080] The compound of the present invention has excellent control effects against ectoparasites and endoparasites that are harmful to humans and animals. In addition, it is a highly safe substance because it has low toxicity to fish and warm-blooded animals. Therefore, it is useful as an active ingredient of a control agent for ectoparasites and endoparasites.

[0081] 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.

[0082] [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 shows a pest control effect. The pesticide is an agent for controlling pests, and includes insecticides or acaricides, external parasite control agents, or internal parasite control or extermination agents.

[0083] [Insecticidal or acaricides] 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.

[0084] 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. In addition, the pesticide, insecticide or acaricide of the present invention is not particularly limited by the species of the plant to which it is applied. Examples of plant species include original species, varieties, improved varieties, cultivated varieties, mutants, hybrids, genetically modified organisms (GMOs), etc. The pest control agent of the present invention can be used for controlling various agricultural pests and mites by seed treatment, foliage spray, soil application, water surface application, and the like.

[0085] Specific examples of various agricultural pests and mites that can be controlled by the pest control agent of the present invention are given below.

[0086] (1) a butterfly or moth of the order Lepidoptera (a) Moths of the family Arctiidae, e.g. Hyphantria cunea, Lemyra imparilis; (b) Moths of the Bucculatricidae family, e.g., Bucculatrix pyrivorella; (c) Moths of the family Carposinidae, e.g., Carposina sasakii; (d) Crambidae moths, for example, Diaphania spp., Diaphania indica, Diaphania nitidalis; for example, Ostrinia spp., Ostrinia furnacalis, Ostrinia nubilalis, Ostrinia scapulalis; and others, Chilo suppressalis, Cnaphalocrocis medinalis, Conogethes punctiferalis, Diatraea grandiosella, Glyphodes pyloalis, 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 family Geometridae, for example, Ascotis selenaria; (g) Moths of the Gracilariidae family, e.g., Caloptilia theivora, Phyllocnistis citrella, and Phyllonorycter ringoniella; (h) butterflies of the Hesperiidae family, for example Parnara guttata; (i) Lasiocampidae moths, such as Malacosoma neustria; (j) Lymantriidae moths, such as Lymantria spp., Lymantria dispar, Lymantria monacha; and others, such as Euproctis pseudoconspersa, Orgyia thyellina;

[0087] (k) moths of the family Lyonetiidae, e.g., Lyonetia spp., Lyonetia clerkella, Lyonetia prunifoliella malinella; (l) Noctuidae moths, for example, Spodoptera spp., Spodoptera depravata, Spodoptera eridania, Spodoptera exigua, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura; for example, Autographa spp., Autographa gamma, Autographa nigrisigna; for example, Agrotis spp., Agrotis ipsilon, Agrotis segetum; for example, Helicoverpa spp., Helicoverpa armigera, Helicoverpa assulta, and Helicoverpa zea; for example, Heliothis spp., Heliothis armigera, and Heliothis virescens; other insects include Aedia leucomelas, Ctenoplusia agnata, Eudocima tyrannus, Mamestra brassicae, Mythimna separata, and Naranga aenescens, Panolis japonica, Peridroma saucia, Pseudoplusia includens, Trichoplusia ni; (m) Moths of the Nolidae family, e.g., Earias insulana; (n) Butterflies of the family Pieridae, e.g., Pieris spp. ) of the large cabbage white butterfly (Pieris brassicae), the cabbage white butterfly (Pieris rapae crucivora); (o) Moths of the Plutellidae family, for example, Acrolepiopsis spp., such as Acrolepiopsis sapporensis and Acrolepiopsis suzukiella; others, such as Plutella xylostella; (p) moths of the family Pyralidae, e.g., Cadra cautella, Elasmopalpus lignosellus, Etiella zinckenella, Galleria mellonella; (q) Moths of the family Sphingidae, e.g., Manduca spp., tomato hornworm (Manduca quinquemaculata), tobacco hornworm (Manduca sexta);

[0088] (r) Moths of the family Stathmopodidae, e.g., Stathmopoda masinissa; (s) Moths of the family Tineidae, e.g., Tinea translucens; (t) Tortricidae moths, such as Adoxophyes spp., Adoxophyes honmai, Adoxophyes orana; Archips spp., Archips breviplicanus, Archips fuscocupreanus; and others, such as Choristoneura fumiferana, Cydia pomonella, Eupoecilia ambiguella, Grapholitha molesta, Homona magnanima, Leguminivore glycinivorella, Lobesia botrana), Matsumuraeses phaseoli, Pandemis heparana, Sparaganothis pilleriana; (u) Moths of the family Yponomeutidae, for example, Argyresthia conjugella.

[0089] (2) Thysanoptera pests (a) Phlaeothripidae, e.g., Ponticulothrips diospyrosi; (b) from the family Thripidae, for example, from the genus Frankliniella, Frankliniella intonsa, Frankliniella occidentalis; from the genus Thrips, for example, Thrips palmi, Thrips tabaci; and others, such as Heliothrips haemorrhoidalis, Scirtothrips dorsalis.

[0090] (3) Hemiptera pests (A)Archaeorrhyncha (a) Delphacidae, for example, Laodelphax striatella, Nilaparvata lugens, Perkinsiella saccharicida, and Sogatella furcifera.

[0091] (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, Balclutha saltuella, Epiacanthus stramineus, Macrosteles striifrons, and Nephotettix cinctinceps.

[0092] (C) Heteroptera (a) Family Alydidae, e.g., Riptortus clavatus; (b) Coreidae, e.g., Cletus punctiger, Leptocorisa chinensis; (c) Family Lygaeidae, e.g. Blissus leucopterus, Cavelerius saccharivorus, Togo hemipterus; (d) Miridae, e.g., Halticus insularis, Lygus lineolaris, Psuedatomoscelis seriatus, Stenodema sibiricum, Stenotus rubrovittatus, Trigonotylus caelestialium;

[0093] (e) Pentatomidae, for example, Nezara spp., Nezara antennata, Nezara viridula; Eysarcoris spp., Eysarcoris aeneus, Eysarcoris lewisi, Eysarcoris ventralis, and others, such as Dolycoris baccarum, Eurydema rugosum, Glaucias subpunctatus, Halyomorpha halys), Piezodorus hybneri, Plautia crossota, Scotinophora lurida; (f) Family Pyrrhocoridae, e.g. Dysdercus cingulatus; (g) Rhopalidae, e.g., Rhopalus msculatus; (h) Scutelleridae, e.g., Eurygaster integriceps; (i) Tingidae, for example, Stephanitis nashi.

[0094] (D) Sternorrhyncha (a) From the family Adelgidae, e.g., Adelges laricis; (b) Aleyrodidae, for example, Bemisia spp., such as silverleaf whitefly (Bemisia argentifolii) and tobacco whitefly (Bemisia tabaci); and others, such as Aleurocanthus spiniferus, Dialeurodes citri, and Trialeurodes vaporariorum; (c) Aphididae, for example, Aphis spp., such as Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis gossypii, Aphis pomi, Aphis sambuci, Aphis spiraecola; for example, Rhopalosiphum spp., such as Rhopalosiphum maidis, Rhopalosiphum padi; for example, Dysaphis spp., such as Dysaphis spp. plantaginea, Dysaphis radicola; for example Macrosiphum spp., Macrosiphum avenae, Macrosiphum euphorbiae; for example Myzus spp.) of the Japanese plum black aphid (Myzus cerasi), the green peach aphid (Myzus persicae), the Japanese burdock aphid (Myzus varians); others include the pea long-horned aphid (Acyrthosiphon pisum), the potato long-horned aphid (Aulacorthum solani), the wheat straw aphid (Brachycaudus helichrysi), the radish aphid (Brevicoryne brassicae), the strawberry long-horned aphid (Chaetosiphon fragaefolii), the peach butterbur aphid (Hyalopterus pruni), the lettuce green aphid (Hyperomyzus lactucae), the false radish aphid (Lipaphis erysimi), the broad bean long-horned aphid (Megoura viciae), Metopolophium dirhodum, Nasonovia ribis-nigri, Phorodon humuli, Schizaphis graminum, Sitobion avenae, Toxoptera aurantii;.

[0095] (d) from the family Coccidae, e.g., 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) from the family Margarodidae, e.g., Drosicha corpulenta, Icerya purchasi; (g) from the family Phylloxeridae, e.g., the grape aphid (Viteus vitifolii); (h) Pseudococcidae, for example, Planococcus spp., such as Planococcus citri, Planococcus kuraunhiae; 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), the pear psylla (Psylla pyrisuga); and others, such as the citrus psylla (Diaphorina citri).

[0096] (4) Pests of the Polyphaga beetle suborder (a) Family 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., Cylas formicarius; (e) Buprestidae, e.g., Agrilus sinuatus; (f) Cerambycidae, e.g. Anoplophora malasiaca, Monochamus alternatus, Psacothea hilaris, Xylotrechus pyrrhoderus; (g) from the family Chrysomelidae, for example, from the genus Bruchus, the pea weevil (Bruchus pisorum), the broad bean weevil (Bruchus rufimanus); from the genus Diabrotica, for example, the northern corn rootworm (Diabrotica barberi), the southern corn rootworm (Diabrotica undecimpunctata), the western corn rootworm (Diabrotica virgifera); from the genus Phyllotreta, for example, the flea beetle (Phyllotreta nemorum), the striped flea beetle (Phyllotreta striolata); and others, such as the cucumber beetle (Aulacophora femoralis), the adzuki bean weevil (Callosobruchus chinensis), the turtle beetle (Cassida nebulosa), Chaetocnema concinna, Colorado beetle (Leptinotarsa ​​decemlineata), Rice leaf beetle (Oulema oryzae), Eggplant long-horned beetle (Psylliodes angusticollis);

[0097] (h) from the family Coccinellidae, for example, from the genus Epilachna, such as Epilachna spp., Epilachna varivestis, Epilachna vigintioctopunctata; (i) Curculionidae, for example, Anthonomus spp., such as Anthonomus grandis and Anthonomus pomorum; Sitophilus spp., such as Sitophilus granarius and Sitophilus zeamais; and others, such as Echinocnemus squameus, Euscepes postfasciatus, Hylobius abietis, Hypera postica, Lissohoptrus oryzophilus, Otiorhynchus spp. sulcatus), red-legged weevil (Sitona lineatus), and grass-leaf weevil (Sphenophorus venatus); (j) from the family Elateridae, for example, Melanotus spp., Melanotus fortnumi, Melanotus tamsuyensis; (k) Nitidulidae, e.g., Epuraea domina; (l) Scarabaeidae, for example, Anomala spp., such as Anomala cuprea and Anomala rufocuprea; others, such as Cetonia aurata, Gametis jucunda, Heptophylla picea, Melolontha melolontha, and Popillia japonica; (m) of the family Scolytidae, e.g., Ips typographus; (n) of the family Staphylinidae, e.g., Paederus fuscipes; (o) Family Tenebrionidae, e.g. Tenebrio molitor, Tribolium castaneum; (p) Of the family Trogossitidae, for example, Tenebroides mauritanicus.

[0098] (5) Diptera pests (A) Flies (Brachycera) (a) Agromyzidae, for example, Liriomyza spp., Liriomyza bryoniae, Liriomyza chinensis, Liriomyza sativae, Liriomyza trifolii; others, Chromatomyia horticola, Agromyza oryzae; (b) from the family Anthomyiidae, e.g., Delia spp., such as Delia platura, cabbage fly, Delia radicum; and others, such as Pegomya cunicularia; (c) Drosophilidae, e.g., Drosophila spp., Drosophila melanogaster, Drosophila suzukii; (d) Ephydridae, e.g., Hydrellia griseola; (e) from the family Psilidae, e.g., the carrot rust fly (Psila rosae); (f) from the family Tephritidae, for example, from the genus Bactrocera spp., Bactrocera cucurbitae, Bactrocera dorsalis; from the genus Rhagoletis spp., for example, Rhagoletis cerasi, Rhagoletis pomonella; and others, for example, Ceratitis capitata, Dacus oleae.

[0099] (B) Nematocera (a) From the family Cecidomyiidae, for example, the soybean pod gall midge (Asphondylia yushimai), the sorghum gall midge (Contarinia sorghicola), the Hessian fly (Mayetiola destructor), and the wheat gall midge (Sitodiplosis mosellana).

[0100] (6) Orthoptera pests (a) Grasshopper family (Acrididae), for example, Schistocerca spp., such as the American locust (Schistocerca americana) and the desert locust (Schistocerca gregaria); others, such as the Australian bush-hopper (Chortoicetes terminifera), the Moroccan locust (Dociostaurus maroccanus), the migratory locust (Locusta migratoria), the brown locust (Locustana pardalina), and the red bush-hopper (Nomadacris septemfasciata); Oxya yezoensis; (b) Family Gryllidae, e.g., Acheta domestica, Teleogryllus emma; (c) Family Gryllotalpidae, e.g., mole cricket (Gryllotalpa orientalis); (d) The family Tettigoniidae, for example, Tachycines asynamorus.

[0101] (7) Mites (Acari) (A) Acaridida, order Astigmata (a) Mites of the family Acaridae, for example, Rhizoglyphus spp., Rhizoglyphus echinopus, Rhizoglyphus robini; for example, Tyrophagus spp., Tyrophagus neiswanderi, Tyrophagus perniciosus, Tyrophagus putrescentiae, Tyrophagus similis; and others, Acarus siro, Aleuroglyphus ovatus, Mycetoglyphus fungivorus;

[0102] (B) Prostigmata (Actinedida) (a) Mites of the family Tetranychidae, for example, Bryobia spp., such as Bryobia praetiosa and 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 suginamensis, Eotetranychus uncatus; for example, Oligonychus spp., Oligonychus hondoensis, Oligonychus ilicis, Oligonychus karamatus, Oligonychus mangiferus, Oligonychus orthius, Oligonychus perseae, Oligonychus pustulosus, Oligonychus shinkajii, Oligonychus ununguis; for example, Panonychus spp., Panonychus citri, Panonychus mori, Panonychus ulmi; for example, Tetranychus spp.) 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, from the Shizotetranychus spp., Shizotetranychus celarius, Shizotetranychus longus, Shizotetranychus miscanthi, Shizotetranychus recki, Shizotetranychus schizopus; and others, Tetranychina harti, Tuckerella pavoniformis, Yezonychus sapporensis;.

[0103] (b) Mites of the Tenuipalpidae family, for example, Brevipalpus spp., such as Brevipalpus lewisi, Brevipalpus obovatus, Brevipalpus phoenicis, Brevipalpus russulus, and Brevipalpus californicus; for example, Tenuipalpus spp., such as Tenuipalpus pacificus and Tenuipalpus zhizhilashviliae; and Dolichotetranychus floridanus; (c) Mites of the family Eriophyidae, for example, Aceria spp., Aceria diospyri, Aceria ficus, Aceria japonica, Aceria kuko, Aceria paradianthi, Aceria tiyingi, Aceria tulipae, Aceria zoysiea; for example, Eriophyes spp., Eriophyes chibaensis, Eriophyes emarginatae; for example, Aculops spp., Aculops tomato lycopersici, Aculops pelekassi; for example, Aculus spp., Aculus fockeui, Aculus schlechtendali; others, Acaphylla theavagrans, Calacarus carinatus, Colomerus vitis, Calepitrimerus vitis, Epitrimerus pyri, Paraphytoptus kikus, Paracalacarus podocarpi, 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., Penthaleus erythrocephalus, Penthaleus major.

[0104] 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 nematocidal activities. The synergistic effect can be confirmed by the Colby formula (Colby. SR; Calculating Synergistic and Antagonistic Responses of Herbicide Combinations; Weeds 15, pp. 20-22, 1967) in accordance with a conventional method.

[0105] 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 (organophosphorus) Acephate, Azamethiphos, Azinphos-ethyl, Azinphosmethyl, 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.

[0106] (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, beta-Cyfluthrin, Cyhalothrin, lambda-Cyhalothrin, gamma-Cyhalothrin, Cypermethrin, alpha-Cypermethrin, beta-Cypermethrin, theta-Cypermethrin, zeta-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.

[0107] (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) GluCl-gated chloride channel (GluCl) allosteric modulators Abamectin, Emamectin, Emamectin-benzoate, Lepimectin, Milbemectin. Doramectin, Eprinomectin, Ivermectin, Moxidectin, Selamectin.

[0108] (7) Juvenile hormone analogues Hydroprene, Kinoprene, Methoprene; Fenoxycarb; Pyriproxifen. Diofenolan, Epophenonane, Triprene. (8) Other non-specific (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 inhibitors Clofentezine, Diflovidazin, Hexythiazox; Etoxazole.

[0109] (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 the proton gradient Chlorfenapyr, DNOC (4,6-dinitro-o-cresol), Sulfluramid. Binapacryl, Dinobuton, Dinocap. (14) Nicotinic acetylcholine receptor (nAChR) channel blockers Bensultap, Cartap hydrochloride, Thiocyclam, Thiosultap-sodium.

[0110] (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 agonists Chromafenozide, Halofenozide, Methoxyfenozide, Tebufenozide.

[0111] (19) Octopamine receptor agonists Amitraz. Chlordimeform. (20) Mitochondrial electron transport complex III inhibitors Hydramethylnon; Acequinocyl; Fluacrypyrim; Bifenazate. (21) Mitochondrial electron transport complex I inhibitors (METI) Fenazaquin, Fenpyroximate, Pyridaben, Pyrimidifen, Tebufenpyrad, Tolfenpyrad; Rotenone. (22) Voltage-dependent sodium channel blockers Indoxacarb; Metaflumizone. (23) Acetyl-CoA carboxylase inhibitors Spirodiclofen, Spiromesifen, Spirotetramat. Spiropidion. (24) Mitochondrial electron transport complex IV inhibitors 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 complex II inhibitors Cyenopyrafen, Cyflumetofen; Pyflubumide.

[0112] (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.

[0113] (31) Other insecticides and acaricides Azadirachtin, Benzoximate, Bromopropylate, Chinomethionat, 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.

[0114] 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, cambendazole; (b) Salicylanilides: closantel, oxyclozanide, rafoxanide, niclosamide; (c) Substituted phenols: nitroxynil, nitrosucrose; (d) Pyrimidines: pyrantel, morantel; (e) Imidazothiazoles: levamisole, tetramisole; (f) Tetrahydropyrimidines: praziquantel, epsiprantel; (g) Other anthelmintics: cyclodiene, ryanine, clorsulon, metronidazole, demiditraz; piperazine, diethylcarbamazine, dichlorophene, monepantel, tribendimidine, amidantel; thiacetaramide, melarsamine, arsenamide.

[0115] 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.

[0116] (B) Agents acting on cytoskeleton and motor proteins B1)~B3) Inhibition of β-tubulin polymerization benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate, thiophanate-methyl, diethofencarb, zoxamide, Ethaboxam. Chlorphenazole, 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.

[0117] (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, flui 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, triphenyltin hydroxide. C7) ATP transport Silthiofam. C8) Complex III: ubiquinone reductase (Qo site, stigmatellin binding subsite) Amethoctradin.

[0118] (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.

[0119] (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.

[0120] (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.

[0121] (G) Inhibitors of sterol biosynthesis in cell membranes G1) C14 demethylase for 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-keto reductase (erg27) in the C4 demethylation of sterol biosynthesis Fenhexamid; fenpyrazamine. G4) Squalene epoxidase (erg1) of the sterol biosynthesis pathway Pyributicarb; naftifine, terbinafine.

[0122] (H) Inhibitors of cell wall biosynthesis H4) Chitin synthase Polyoxin. Polyoxorim. H5) Cellulose synthase dimethomorph, flumorph, pyrimorph; Benthiavalicarb, iprovalicarb, valifenalate; mandipropamid.

[0123] (I) Inhibitors of cell wall melanin synthesis I1) Reductases in melanin biosynthesis Fthalide; pyroquilon; tricyclazole. I2) Dehydratase of melanin biosynthesis Carpropamid; diclocymet; fenoxanil. I3) Polyketide synthase in melanin biosynthesis Tolprocarb.

[0124] (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 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

[0125] (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, pyridachlometyl, pyrapropoyne, aminopyrifen, ipfentrifluconazole, quinofumelin, dipymetitrone.

[0126] (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; sulphur, lime sulfur; amobam, ferbam, mancozeb, maneb, metiram, propineb, thiram, zinc thiazole thiazole, zineb, ziram; captan, captafol, folpet; chlorothalonil; dichlofluanid, tolylfluanid; guazatine, guazatine acetates, iminoctadine, iminoctadine triacetate, iminoctadine trialbesilate; anilazine; dithianon; chinomethionat; fluoroimide; methasulfocarb. Dazomet, cufraneb, mancopper, polycarbamate.

[0127] (BM01) Biological Control Agents with Multiple Modes of Action / Biological Control Agents extract from the cotyledons of lupine plantlets;extract from Swinglea glutinosa;extract from Melaleuca alternifolia (tea tree oil);plant oils (mixtures): eugenol, geraniol, thymol.

[0128] (BM02) Biological Control Agents with Multiple Modes of Action / Biological Control Agents 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 cerevisae 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.

[0129] 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, f Ethylthiol, 1-naphthylacetamide, ethychlozate, cloxyfonac, 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.

[0130] [External parasite control agent] The ectoparasite control 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 control agent of the present invention is not particularly limited as long as it shows an effect of controlling ectoparasites.

[0131] 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., cows, 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, buffaloes, 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.

[0132] The ectoparasite control agent of the present invention can be administered by known veterinary methods (topical, oral, parenteral or subcutaneous administration). The methods include oral administration to animals by tablets, capsules, inclusion in feed, etc.; administration to animals by immersion, suppository, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.); local administration by spraying, pour-on, spot-on, etc. of an oil-based or aqueous liquid; kneading the ectoparasite control agent into a resin, forming the kneaded product into an appropriate shape such as a collar or ear tag, and attaching the kneaded product to an animal for local administration; Some examples include:

[0133] Ectoparasites parasitize in and on host animals, particularly warm-blooded animals. Specifically, they parasitize on the back, armpits, lower abdomen, inner thighs, etc. of the host animal and live by obtaining nutrients such as blood and dandruff 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.

[0134] (1) Mites (Acari) Mites that parasitize insects, such as mites from the Dermanyssidae family, Macronyssidae family, Laelapidae family, Varroidae family, Argasidae family, Ixodidae family, Psoroptidae family, Sarcoptidae family, Knemidokoptidae family, Demodixidae family, Trombiculidae family, and stag beetle mites. (2) Phthiraptera Lice from the family Haematopinidae, lice from the family Linognathidae, lice from the family Menoponidae, lice from the family Philopteridae, and lice from the family Trichodectidae. (3) Siphonaptera Fleas of the family Pulicidae, for example, Ctenocephalides spp., Ctenocephalides canis, Ctenocephalides felis; Fleas of the Tungidae family, Ceratophyllidae family, and Leptopsyllidae family. (4) Hemiptera. (5) Pests of the order Diptera: Mosquitoes of the family Culicidae, black flies of the family Simuliidae, midges of the family Ceratopogonidae, horseflies of the family Tabanidae, flies of the family Muscidae, sheathe flies of the family Glossinidae, flesh flies of the family Flesh flies, flies of the family Hippoboscidae, flies of the family Calliphoridae, flies of the family Oestridae.

[0135] [Internal parasite control or extermination agents] The internal parasite control or extermination 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 internal parasite control or extermination agent of the present invention is not particularly limited as long as it shows an effect of controlling internal parasites.

[0136] The parasites targeted by the endoparasite control or extermination agent of the present invention are parasitic in host animals, particularly warm-blooded animals and fish (endoparasites). 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., cows, 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, buffaloes, etc.), poultry (turkeys, ducks, chickens, quails, geese, etc.), and pet birds (pigeons, parrots, mynah birds, Java sparrows, parakeets, Bengalese finches, canaries, etc.); or fish such as salmon, trout, and koi carp. Controlling and eradicating parasites can prevent or treat parasitic diseases transmitted by the parasites.

[0137] Parasites to be controlled or eradicated include the following: (1) Nematodes of the order Dioctophymatida (a) Kidney worms of the family Dioctophymatidae, e.g., Dioctophyma spp., Dioctophyma renale; (b) Kidney worms of the family Soboliphymatidae, e.g., Soboliphyme spp., Soboliphyme abei, Soboliphyme baturini.

[0138] (2) Nematodes of the order Trichocephalida (a) Trichinella of the family Trichinellidae, such as Trichinella spiralis of the genus Trichinella spp.; (b) whipworms of the family Trichuridae, for example, Capillaria spp., Capillaria annulata, Capillaria contorta, Capillaria hepatica, Capillaria perforans, Capillaria plica, Capillaria suis; Trichuris spp., Trichuris vulpis, Trichuris discolor, Trichuris ovis, Trichuris skrjabini, Trichuris suis.

[0139] (3) Rhabditida nematodes Strongyloides of the family Strongyloididae, for example, Strongyloides spp., Strongyloides papillosus, Strongyloides planiceps, Strongyloides ransomi, Strongyloides suis, Strongyloides stercoralis, Strongyloides tumefaciens, Strongyloides ratti.

[0140] (4) Strongylida nematodes Hookworms of the family Ancylostomatidae, for example, from the genus Ancylostoma, Ancylostoma braziliense, Ancylostoma caninum, Ancylostoma duodenale, Ancylostoma tubaeforme; from the genus Uncinaria, Uncinaria stenocephala; from the genus Bunostomum, Bunostomum phlebotomum, Bunostomum trigonocephalum.

[0141] (5) Strongylida nematodes (a) Nematodes of the family Angiostrongylidae, for example, Aelurostrongylus spp., Aelurostrongylus abstrusus; Angiostrongylus spp., Angiostrongylus vasorum, Angiostrongylus cantonesis; (b) Nematodes of the family Crenosomatidae, 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, e.g., Metastrongylus spp., Metastrongylus apri, Metastrongylus asymmetricus, Metastrongylus pudendotectus, Metastrongylus salmi; (e) Open-beaked worms of the family Syngamidae, 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).

[0142] (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, e.g., Ostertagia spp., Ostertagia ostertagi; (e) Nematodes of the family Heligmonellidae, e.g., Nippostrongylus spp., mouse strongyle (Nippostrongylus braziliensis); (f) Nematodes of the family Trichostrongylidae, for example, Trichostrongylus spp., Trichostrongylus axei, Trichostrongylus colubriformis, Trichostrongylus tenuis; Hyostrongylus spp., Hyostrongylus rubidus; Obeliscoides spp., Obeliscoides cuniculi.

[0143] (7) Strongylida nematodes (a) Nematodes of the family Chabertiidae, for example, Chabertia spp., Chabertia ovina; Oesophagostomum spp., Oesophagostomum brevicaudatum, Oesophagostomum columbianum, Oesophagostomum dentatum, Oesophagostomum georgianum, Oesophagostomum maplestonei, Oesophagostomum quadrispinulatum, Oesophagostomum radiatum, Oesophagostomum venulosum, Oesophagostomum scrofa watanabei); (b) Nematodes of the family Stephanuridae, e.g., Stephanurus spp., Stephanurus dentatus ; (c) Nematodes of the family Strongylidae, for example, Strongylus spp., such as Strongylus asini, Strongylus edentatus, Strongylus equinus, and Strongylus vulgaris.

[0144] (8) Nematodes of the order Oxyurida Nematodes of the family Oxyuridae, e.g., Enterobius spp., Enterobius anthropopitheci, Enterobius vermicularis; Oxyuris spp., horse pinworms (Oxyuris equi); Passalurus spp., rabbit pinworms (Passalurus ambiguus).

[0145] (9) Nematodes of the order Ascaridida (a) Nematodes of the family Ascaridiidae, e.g., Ascaridia spp., Ascaridia galli; (b) Nematodes of the family Heterakidae, e.g., Heterakis spp., Heterakis beramporia, Heterakis brevispiculum, Heterakis gallinarum, Heterakis pusilla, Heterakis putaustralis; (c) nematodes of the family Anisakidae, e.g., Anisakis spp., Anisakis simplex; (d) Nematodes of the family Ascarididae, e.g., Ascaris spp., Ascaris lumbricoides, Ascaris suum; Parascaris spp., Parascaris equorum; (e) Nematodes of the family Toxocaraidae, for example, Toxocara spp., Toxocara canis, Toxocara leonina, Toxocarasuum, Toxocara vitulorum, and Toxocara cati.

[0146] (10) Nematodes of the order Spirurida (a) Nematodes of the family Onchocercidae, for example, Brugia spp., Brugia malayi, Brugia pahangi, Brugia patei; Dipetalonema spp., Dipetalonema reconditum; Dirofilaria spp., Dirofilaria immitis; Filaria spp., Filaria oculi; Onchocerca spp., Onchocerca cervicalis, Onchocerca gibsoni; Pharyngeal heartworm (Onchocerca gutturosa); (b) Nematodes of the family Setariidae, e.g., Setaria spp., Setaria digitata, Setaria equina, Setaria labiatopapillosa, Setaria marshalli; Wuchereria spp., Wuchereria bancrofti; (c) Nematodes of the family Filariidae, for example, Parafilaria spp., Parafilaria multipapillosa; Stephanofilaria spp., Stephanofilaria assamensis, Stephanofilaria dedoesi, Stephanofilaria kaeli, Stephanofilaria okinawaensis, Stephanofilaria stilesi.

[0147] (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, e.g., Habronema spp., Habronema majus, Habronema microstoma, Habronema muscae; Draschia spp., 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, Physaloptera sibirica, Physaloptera 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., Thelazia callipaeda, Thelazia gulosa, Thelazia lacrymalis, Thelazia rhodesi, and Thelazia skrjabini.

[0148] [Control agents for other pests] In addition, the compound of the present invention is highly 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.).

[0149] Specific examples are given below. (1) Hymenoptera pests bees of the Argidae family, bees of the Cynipidae family, bees of the Diprionidae family, ants of the Formicidae family, bees of the Mutillidae family, and bees of the Vespidae family.

[0150] (2) Other pests Cockroaches (Blattodea), termites (termite), spiders (Araneae), centipedes (cetipede), millipedes (millipede), crustacea, and bedbugs (Cimex lectularius).

[0151] [Formulation] Some formulations of the pesticide, insecticide or acaricide, external parasite control agent, or internal parasite control or extermination agent of the present invention are shown below, but the additives and the addition ratios should not be limited to these examples and can be changed in 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.

[0152] (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 ground 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 having an active ingredient content of 30%. (Formulation 3: Granules) 5 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 having a diameter of 0.5 to 1.0 mm to obtain a granule containing 5% of the active ingredient. (Formulation 4: Granules) 5 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 then 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 sodium polycarboxylate, 10 parts of glycerin, 0.2 parts of xanthan gum, and 73.8 parts of water are mixed and wet-pulverized until the particle size is 3 microns or less to obtain a suspension containing 10% of the active ingredient.

[0153] 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 sprayed onto 94 parts of kaolin and 1 part of white carbon, and then the solvent is 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 through 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 myristic acid ester, and 85 parts of isopropanol. (Formulation 9: Spot-on agent) 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 agent is obtained by uniformly mixing 1 part of the compound of the present invention, 10 parts of propylene glycol, and 89 parts of isopropanol.

[0154] The present invention will now be described in more detail with reference to examples, although the present invention is not limited to the following examples in any way.

[0155] Example 1 In the following steps, (Z)-4-(5-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-1-methyl-1H-imidazol-2-yl)-5-(ethylsulfonyl)-2,2'-bipyrimidine (Compound Number 1) was synthesized.

[0156] (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

[0157] TIFF2025026809000005.tif29140

[0158] (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 thereto and 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%).1 The H-NMR spectrum 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). As described in Non-Patent Document 1, the crossed double bond indicates an unspecified double bond configuration or a mixture of different configurations.

[0159] (Process 2) Synthesis of (Z)-4-(5-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-1-methyl-1H-imidazol-2-yl)-5-(ethylsulfonyl)-2,2'-bipyrimidine

[0160] TIFF2025026809000006.tif45162

[0161] 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 (0.18 g) was dissolved in ethanol (7 ml) and stirred at room temperature. Triethylamine (0.13 g) and 2-amidinopyrimidine hydrochloride (0.08 g) were added thereto and stirred under heating and reflux for 1 hour. The resulting liquid was concentrated, and the concentrate was purified by silica gel column chromatography to obtain 0.15 g of the target product (yield 30%). 1 The H-NMR spectrum is shown below. 1 H-NMR(400 MHz, CDCl3): δ 9.64 (s, 1H), 9.08 (d, 2H), 8.10 (s, 1H), 7.54 (t, 1H), 7.19 (s, 1H), 4.09 (q, 2H), 3.94 (s, 3H), 1.44 (t, 3H).

[0162] Through the same process as in Example 1, the compounds shown in Table 1 below were synthesized.

[0163] [Table 1]

[0164] [Biological Testing] The usefulness of the compound of the present invention as an active ingredient in pest control agents and ectoparasite control agents will be demonstrated in the following test examples, in which "parts" are by weight.

[0165] (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 and dissolved to prepare an emulsifiable concentrate (I) containing 5% of the active ingredient.

[0166] The mortality rate was calculated according to the following formula: Insect killing rate (%) = (number of dead insects / number of test insects) x 100

[0167] (Test Example 1) Efficacy test against armyworm Emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm. Corn leaf pieces were immersed in the diluted solution for 30 seconds. The corn leaf pieces were placed in a petri dish, and five second-instar larvae of the armyworm were released. The petri dishes were left in a thermostatic chamber at a temperature of 25°C and a humidity of 60% during the test period. Six days after the release of the insects, the survival rate was determined and the mortality rate was calculated. The test was performed in duplicate. The compounds Nos. 1, 2, 3, 4, and 5 were tested for efficacy against the armyworm, and all of the compounds showed a killing rate of 80% or more.

[0168] (Test Example 2) Efficacy test against diamondback moth Emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 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 the release, the live and dead insects were judged, and the insecticidal rate was calculated. The test was performed in duplicate. Efficacy tests against diamondback moth were carried out for compound numbers 1, 2, 3, 4, and 5. All of the compounds showed insecticidal rates of 80% or more.

[0169] (Test Example 3) Efficacy test against striped flea beetles Emulsion (I) was diluted with water to a concentration of the compound of the present invention of 125 ppm to prepare a test solution. The test solution was sprayed on 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 (Phyllotreta striolata) were released into the cups. The cups were stored in a thermostatic chamber at a temperature of 25°C and a humidity of 65%, and after 7 days from the release, a live / dead count was performed to calculate the insecticidal rate. The test was performed in duplicate. Efficacy tests against adult flea beetles were carried out on compound numbers 1, 2, 3, 4, and 5. All of the compounds showed insecticidal rates of 80% or more.

[0170] (Test Example 4) Efficacy test against Thrips palmi Eight adult Thrips palmi were inoculated onto cucumber seedlings. The emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm. The diluted solution was sprayed onto cucumber seedlings and air-dried. The number of parasitic larvae was counted 7 days after spraying. The efficacy of the compound was evaluated based on the control rate shown below. Control rate (%) = {1- (Nt) / (Nc)} x 100 Nt: Number of parasites in the area where the diluted solution was sprayed Nc: Number of parasites in the area without dilution Efficacy tests against Thrips palmi were carried out on Compound Nos. 1, 2, 3, 4, and 5. All of the compounds showed a control rate of 80% or more.

[0171] (Test Example 5) 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 the isopropanol was evaporated by air drying to form a thin film of the compound of the present invention. Five 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. The test was performed in duplicate. Efficacy tests against adult cat fleas were carried out on compound numbers 1, 2, 3, 4, and 5. All of the compounds showed insecticidal rates of 80% or more.

[0172] Since all of the heteroarylpyrimidine compounds randomly selected from the heteroarylpyrimidine compounds of the present invention have the above-mentioned effects, it can be understood that the heteroarylpyrimidine compounds of the present invention, including the compounds not listed as examples, are compounds that have pest control effects, particularly acaricidal and insecticidal effects. It can also be understood that the compounds are compounds that have effects on parasites that are harmful to humans and livestock, such as external parasites.

Claims

1. A compound represented by formula (I) or a salt thereof: [In formula (I), R １ is a substituted or unsubstituted C2-6 alkenyl group, or a substituted or unsubstituted C2-6 alkynyl group, R 2 is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a halogeno group, R 3 is a substituted or unsubstituted C1-6 alkyl group, X １ and X ２ are each independently 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 hydroxyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted A C1-6 alkylsulfonyl 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 phenoxy group, a substituted or unsubstituted naphthoxy group, a substituted or unsubstituted 5-10 membered heterocyclyloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aminocarbonyl group, a nitro group, a cyano group, a halogeno group, or -C(R ｃ ) = N-OR ｄ is a group represented by R ｃ is a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group, R ｄ is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, or a C2-6 alkynyl group, Y is -S(=O) ｎ -, or -S(=O)(=NR Ｎ )- is a group represented by n represents the number of =O and is an integer of 0 to 2; R Ｎ is 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 C1-6 alkylsulfonyl 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 heteroaryl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aminocarbonyl group, a nitro group, or a cyano group.]

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

3. 13. An insecticide or acaricide comprising as an active ingredient at least one selected from the group consisting of the compound according to claim 1 and its salts.

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

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 its salt.

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