Piperidone derivative or salt thereof, pest control agent containing same, and method for using same

Abstract

In crop production in agriculture, horticulture and the like, harm caused by pests and the like is still huge now, and a novel pest control agent for agriculture and horticulture is expected to be developed due to factors such as generation of pests tolerant to existing drugs. Furthermore, when animals such as livestock and pet animals are raised, infection of parasites brings significant pain to the animals, and enormous economic loss is caused in the livestock, so it is necessary to develop a novel external parasite control agent for animals and an internal parasite control agent for animals. The present invention provides: a compound represented by general formula (1) (in the formula, X represents CH2 or an oxygen atom, Y represents an oxygen atom or a sulfur atom, R1 represents a substituted phenyl group or the like, R2 represents a substituted phenyl group or the like, and R3 represents a hydrogen atom or the like) or a salt thereof; a pest control agent containing the compound as an active ingredient; and a method for using the pest control agent. # imgabs0 #

Description

Technical Field

[0001] The present invention relates to piperidone derivatives or their salts, harmful organism control agents containing the compounds and methods of using the same. Background Art

[0002] Patent Document 1 reports a certain piperidone derivative as an intermediate of a pharmaceutical compound. However, the document does not describe or suggest the control activity of the compound against harmful organisms such as agricultural and horticultural pests or animal parasites. Prior art literature Patent Literature

[0003] Patent Document 1: International Publication No. 2017 / 102649 Pamphlet Summary of the invention Problems to be solved by the invention

[0004] In the production of useful crops such as agriculture and gardening, the harm caused by pests is very large, and effective agricultural and gardening pest control agents are listed in a large number. However, due to the high effect of the resistant pests for existing drugs, the excellent human and animal safety of the medicaments, the requirements of the environmental safety excellent medicaments such as the medicaments with the physical properties suitable for various labor-saving application methods, the medicaments with the properties suitable for various labor-saving application methods, the acute toxicity, etc., the development of novel agricultural and gardening pest control agents is still one of the important topics in the agricultural and gardening field. In addition, in animal breeding such as livestock, play animals (pets), the prevention and control of parasites is also an important topic. The infection of parasites, in addition to itself, the diseases caused by viruses, bacteria, etc. transmitted by parasites will bring significant pain to animals, and become huge economic losses in livestock, so it is necessary to develop novel external parasite control agents for animals and internal parasite control agents for animals. Means for solving problems

[0005] The present inventors have repeatedly conducted intensive studies in order to develop new pest control agents, particularly agricultural and horticultural pest control agents, external parasite control agents for animals, and internal parasite control agents for animals. As a result, they have found that the compounds represented by the general formula (1) of the present invention, which have a piperidinone derivative as a carboxylic acid site of a carboxamide, or salts thereof are useful as pest control agents, thereby completing the present invention.

[0006] That is, the present invention relates to: [1] A compound represented by the general formula (1) and a salt thereof, [Chemical formula 1] {where, R 1 express (a1) (C1-C6) alkyl; (a2) (C2-C6) alkenyl; (a3) (C2-C6) alkynyl; (a4) (C3-C6) cycloalkyl; (a5) halo(C1-C6)alkyl; (a6) halo(C2-C6)alkenyl; (a7) halo(C2-C6)alkynyl; (a8) halo(C3-C6)cycloalkyl; (a9) a substituted (C1-C6)alkyl group having 1 to 3 substituents each independently selected from Substituent Group A; (a10) a substituted (C3-C6)cycloalkyl group having 1 to 3 substituents each independently selected from Substituent Group B; (a11) phenyl(C1-C6)alkyl (excluding phenylmethyl); (a12) a substituted phenyl (C1-C6) alkyl group having 1 to 5 substituents each independently selected from Substituent Group C on the ring; (a13) pyridyl(C1-C6)alkyl; (a14) a substituted pyridyl(C1-C6)alkyl group having 1 to 4 substituents independently selected from Substituent Group C on the ring; (a15) (C1-C6) alkylcarbonyl; (a16) halo(C1-C6)alkylcarbonyl; (a17) a substituted (C1-C6)alkylcarbonyl group having 1 to 3 substituents each independently selected from Substituent Group A; (a18) phenylcarbonyl; (a19) a substituted phenylcarbonyl group having 1 to 5 substituents each independently selected from Substituent Group C on the ring; (a20) pyridylcarbonyl; (a21) a substituted pyridylcarbonyl group having 1 to 4 substituents each independently selected from Substituent Group C on the ring; (a22) furanylcarbonyl; (a23) a substituted furanylcarbonyl group having 1 to 3 substituents each independently selected from Substituent Group C on the ring; (a24) thienylcarbonyl; (a25) a substituted thienylcarbonyl group having 1 to 3 substituents each independently selected from Substituent Group C on the ring; (a26) pyrazolylcarbonyl; (a27) a substituted pyrazolylcarbonyl group having 1 to 3 substituents each independently selected from Substituent Group C on the ring; (a28) triazolylcarbonyl; (a29) a substituted triazolylcarbonyl group having 1 to 2 substituents each independently selected from Substituent Group C on the ring; (a30) dioxodihydrodibenzofuranylcarbonyl; (a31) a substituted dioxodihydrodibenzofuranylcarbonyl group having 1 to 3 substituents each independently selected from Substituent Group C on its ring; (a32) dihydrobenzodioxinylcarbonyl; (a33) a substituted dihydrobenzodioxinylcarbonyl group having 1 to 7 substituents each independently selected from Substituent Group C on its ring; (a34) (C1-C6) alkoxycarbonyl; (a35) halo(C1-C6)alkoxycarbonyl; (a36) a substituted (C1-C6)alkoxycarbonyl group having 1 to 3 substituents each independently selected from Substituent Group A; (a37) phenyl(C1-C6)alkoxycarbonyl; (a38) a substituted phenyl(C1-C6)alkoxycarbonyl group having 1 to 5 substituents each independently selected from Substituent Group C; (a39) (C1-C6) alkylsulfonyl; (a40) (C3-C6) cycloalkylsulfonyl; (a41) halo(C1-C6)alkylsulfonyl; (a42) halo(C3-C6)cycloalkylsulfonyl; (a43) a substituted (C1-C6)alkylsulfonyl group having 1 to 3 substituents each independently selected from Substituent Group A; (a44) a substituted (C3-C6)cycloalkylsulfonyl group having 1 to 3 substituents each independently selected from Substituent Group B; (a45) halo(C1-C6)alkoxyhalo(C1-C6)alkylsulfonyl; (a46) phenylsulfonyl; (a47) a substituted phenylsulfonyl group having 1 to 5 substituents each independently selected from Substituent Group C; (a48) thienylsulfonyl; (a49) a substituted thienylsulfonyl group having 1 to 3 substituents each independently selected from Substituent Group C on the ring; (a50) pyrazolylsulfonyl; (a51) a substituted pyrazolylsulfonyl group having 1 to 3 substituents each independently selected from Substituent Group C on the ring; (a52) thiazolylsulfonyl; (a53) a substituted thiazolylsulfonyl group having 1 to 2 substituents each independently selected from Substituent Group C on the ring; (a54) isoxazolylsulfonyl; (a55) a substituted isoxazolylsulfonyl group having 1 to 2 substituents each independently selected from Substituent Group C on the ring; (a56) quinolylsulfonyl; (a57) a substituted quinolylsulfonyl group having 1 to 6 substituents each independently selected from Substituent Group C on the ring; (a58) phenyl(C1-C6)alkylsulfonyl; (a59) a substituted phenyl (C1-C6) alkylsulfonyl group having 1 to 5 substituents each independently selected from Substituent Group C; (a60) aryl; (a61) a substituted aryl group having one or more substituents each independently selected from the substituent group D on the ring; (a62) a 5- to 10-membered heterocyclic group; (a63) a substituted 5- to 10-membered heterocyclic group having at least one substituent each independently selected from the substituent group D on the ring; (a64) (C3-C6) cycloalkylcarbonyl; (a65) a substituted (C3-C6)cycloalkylcarbonyl group having 1 to 3 substituents each independently selected from Substituent Group B; (a66) isoxazolylcarbonyl; (a67) a substituted isoxazolylcarbonyl group having 1 to 2 substituents each independently selected from Substituent Group C on the ring; (a68) phenylaminocarbonyl; (a69) a substituted phenylaminocarbonyl group having 1 to 5 substituents each independently selected from Substituent Group C on the ring; (a70) pyrimidinylcarbonyl; (a71) a substituted pyrimidinylcarbonyl group having 1 to 3 substituents each independently selected from Substituent Group C on the ring; (a72) pyrazinylcarbonyl; (a73) a substituted pyrazinylcarbonyl group having 1 to 3 substituents each independently selected from Substituent Group C on the ring; (a74) pyridazinylcarbonyl; (a75) a substituted pyridazinylcarbonyl group having 1 to 3 substituents each independently selected from Substituent Group C on the ring; (a76) naphthylcarbonyl; (a77) a substituted naphthylcarbonyl group having 1 to 7 substituents each independently selected from Substituent Group C on the ring; (a78) quinolylcarbonyl; or (a79) A substituted quinolylcarbonyl group having 1 to 6 substituents each independently selected from Substituent Group C on its ring. R 2 express (b1) amino group; (b2) (C1-C6) alkyl; (b3) (C2-C6) alkenyl; (b4) (C2-C6) alkynyl; (b5) (C3-C6) cycloalkyl; (b6) halo(C1-C6)alkyl; (b7) halo(C2-C6)alkenyl; (b8) halo(C2-C6)alkynyl; (b9) halo(C3-C6)cycloalkyl; (b10) a substituted (C1-C6)alkyl group having 1 to 3 substituents each independently selected from Substituent Group A; (b11) a substituted (C3-C6)cycloalkyl group having 1 to 3 substituents each independently selected from Substituent Group B on the ring; (b12) N-(C1-C6)alkylamino; (b13) N,N-di(C1-C6)alkylamino; (b14) N-(C1-C6)alkyl-N-phenylamino; (b15) (C1-C6) alkylsulfonyl; (b16) N-(C1-C6)alkylaminosulfonyl; (b17) N,N-di(C1-C6)alkylaminosulfonyl; (b18) piperidinyl; (b19) morpholinyl; (b20) phenyl; (b21) a substituted phenyl group having 1 to 5 substituents independently selected from the substituent group E on the ring; (b22) pyridyl; (b23) a substituted pyridyl group having 1 to 4 substituents independently selected from the substituent group E on the ring; (b24) pyridazinyl; (b25) a substituted pyridazinyl group having 1 to 3 substituents each independently selected from Substituent Group E on the ring; (b26) pyrimidinyl; (b27) a substituted pyrimidinyl group having 1 to 3 substituents each independently selected from Substituent Group E on the ring; (b28) pyrazinyl; (b29) a substituted pyrazinyl group having 1 to 3 substituents each independently selected from Substituent Group E on the ring; (b30) triazine group; (b31) a substituted triazine group having 1 to 2 substituents each independently selected from the substituent group E on the ring; (b32) furanyl; (b33) a substituted furanyl group having 1 to 3 substituents each independently selected from Substituent Group E on the ring; (b34) oxazolyl; (b35) substituted oxazolyl having 1 to 2 substituents independently selected from Substituent Group E on the ring; (b36) isoxazolyl; (b37) a substituted isoxazolyl group having 1 to 2 substituents each independently selected from Substituent Group E on the ring; (b38) thienyl; (b39) a substituted thienyl group having 1 to 3 substituents each independently selected from Substituent Group E on the ring; (b40) thiazolyl; (b41) a substituted thiazolyl group having 1 to 2 substituents each independently selected from the substituent group E on the ring; (b42) isothiazolyl; (b43) a substituted isothiazolyl group having 1 to 2 substituents each independently selected from the substituent group E on the ring; (b44) thiadiazolyl; (b45) a substituted thiadiazolyl group having on its ring 1 substituent each independently selected from Substituent Group E; (b46) pyrazolyl; (b47) a substituted pyrazolyl group having 1 to 3 substituents each independently selected from Substituent Group E on the ring; (b48) triazolyl; (b49) a substituted triazole group having 1 to 2 substituents each independently selected from the substituent group E on the ring; (b50) tetrazolyl; (b51) a substituted tetrazolyl group having 1 substituent on the ring, each independently selected from Substituent Group E; (b52) benzoxazolyl; (b53) a substituted benzoxazolyl group having 1 to 4 substituents independently selected from Substituent Group E on the ring; (b54) benzothiazolyl; (b55) a substituted benzothiazolyl group having 1 to 4 substituents each independently selected from Substituent Group E on the ring; (b56)quinolinyl; (b57) a substituted quinolyl group having 1 to 6 substituents each independently selected from Substituent Group E on the ring; (b58) naphthyl; (b59) a substituted naphthyl group having 1 to 7 substituents each independently selected from Substituent Group E on the ring; (b60) tetrahydronaphthyl; (b61) a substituted tetrahydronaphthyl group having 1 to 10 substituents each independently selected from Substituent Group E on the ring; (b62) phenyl(C1-C6)alkyl; (b63) substituted phenyl (C1-C6) alkyl having 1 to 5 substituents independently selected from Substituent Group E on the ring; (b64) pyridyl(C1-C6)alkyl; (b65) a substituted pyridyl(C1-C6)alkyl group having 1 to 4 substituents independently selected from Substituent Group E on the ring; (b66) pyrazinyl(C1-C6)alkyl; (b67) a substituted pyrazinyl(C1-C6)alkyl group having 1 to 3 substituents independently selected from Substituent Group E on the ring; (b68) pyrimidinyl(C1-C6)alkyl; (b69) a substituted pyrimidinyl (C1-C6) alkyl group having 1 to 3 substituents each independently selected from Substituent Group E on the ring; (b70) furanyl (C1-C6) alkyl; (b71) a substituted furanyl (C1-C6) alkyl group having 1 to 3 substituents each independently selected from Substituent Group E on the ring; (b72) thienyl(C1-C6)alkyl; (b73) a substituted thienyl(C1-C6)alkyl group having 1 to 3 substituents independently selected from Substituent Group E on the ring; (b74) tetrahydrofuranyl (C1-C6) alkyl; (b75) a substituted tetrahydrofuranyl (C1-C6) alkyl group having 1 to 3 substituents each independently selected from Substituent Group E on the ring; (b76) benzimidazolyl; or (b77) A substituted benzimidazolyl group having 1 to 5 substituents each independently selected from Substituent Group E on the ring. R3 express (c1) hydrogen atom; (c2)(C1-C6)alkyl; (c3)(C3-C6)cycloalkyl; (c4)(C1-C6)alkoxy; or (c5) (C1-C6) alkylcarbonyl. R 2 and R 3 They may be bonded to each other to form a ring. X represents CH2 or an oxygen atom. Y represents an oxygen atom or a sulfur atom. Substituent group A includes: (d1) cyano; (d2) (C1-C6) alkyl; (d3) (C2-C6) alkenyl; (d4) (C2-C6) alkynyl; (d5) (C3-C6) cycloalkyl; (d6) (C1-C6) alkoxy; (d7) (C1-C6) alkylthio; (d8) (C1-C6) alkylsulfinyl; (d9) (C1-C6) alkylsulfonyl; (d10) halo(C1-C6)alkyl; (d11) halo(C3-C6)cycloalkyl; (d12) halogenated (C1-C6) alkoxy; (d13) halo(C1-C6)alkylthio; (d14) halo(C1-C6)alkylsulfinyl; (d15) halo(C1-C6)alkylsulfonyl; (d16) phenylthio; (d17) aminocarbonyl; (d18) morpholinyl; (d19) phenylcarbonyl; (d20) a substituted phenylcarbonyl group having 1 to 5 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (d21) pyrazolyl; (d22) a substituted pyrazolyl group having 1 to 3 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (d23) thienyl; and (d24) A substituted thienyl group having 1 to 3 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group. Substituent Group B includes: (e1) cyano; (e2) (C1-C6) alkyl; (e3) (C2-C6) alkenyl; (e4) (C2-C6) alkynyl; (e5) (C3-C6) cycloalkyl; (e6) (C1-C6) alkoxy; (e7) (C1-C6) alkylthio; (e8) (C1-C6) alkylsulfinyl; (e9) (C1-C6) alkylsulfonyl; (e10) halo(C1-C6)alkyl; (e11) halo(C3-C6)cycloalkyl; (e12) halogenated (C1-C6) alkoxy; (e13) halo(C1-C6)alkylthio; (e14) halo(C1-C6)alkylsulfinyl; (e15) halo(C1-C6)alkylsulfonyl; (e16) aminocarbonyl; and (e17) Phenyl. Substituent group C includes: (f1) halogen atom; (f2) cyano; (f3) nitro; (f4) hydroxyl group; (f5) carboxyl group; (f6) (C1-C6) alkyl; (f7) (C2-C6) alkenyl; (f8) (C2-C6) alkynyl; (f9) (C1-C6) alkoxy; (f10) (C3-C6) cycloalkyl; (f11) (C1-C6) alkylthio; (f12) (C1-C6) alkylsulfinyl; (f13) (C1-C6) alkylsulfonyl; (f14) halo(C1-C6)alkyl; (f15) halo(C2-C6)alkenyl; (f16) halo(C2-C6)alkynyl; (f17) halogenated (C1-C6) alkoxy; (f18) halo(C3-C6)cycloalkyl; (f19) halo(C1-C6)alkylthio; (f20) halo(C1-C6)alkylsulfinyl; (f21) halo(C1-C6)alkylsulfonyl; (f22) (C1-C6) alkylcarbonyl; (f23) (C1-C6) alkoxycarbonyl; (f24) phenyl; (f25) a substituted phenyl group having 1 to 5 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (f26) phenoxy; (f27) a substituted phenoxy group having 1 to 5 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (f28) a methylenedioxy group formed by two adjacent substituents together, which may be substituted by 1 to 2 substituents selected from the group consisting of a halogen atom, a phenyl group and a (C1-C6) alkyl group; (f29) (C1-C6) alkylcarbonylamino; (f30) halo(C1-C6)alkylcarbonylamino; and (f31) (C1-C6)alkylthio (C1-C6)alkylaminocarbonyl. Substituent group D includes: (g1) a halogen atom; (g2) cyano; (g3) nitro; (g4) hydroxyl group; (g5) carboxyl group; (g6) (C1-C6) alkyl; (g7)(C2-C6)alkenyl; (g8) (C2-C6) alkynyl; (g9) (C1-C6) alkoxy; (g10) (C3-C6) cycloalkyl; (g11)(C1-C6)alkylthio; (g12) (C1-C6) alkylsulfinyl; (g13) (C1-C6) alkylsulfonyl; (g14) halo(C1-C6)alkyl; (g15) halo(C2-C6)alkenyl; (g16) halo(C2-C6)alkynyl; (g17) halogenated (C1-C6) alkoxy; (g18) halo(C3-C6)cycloalkyl; (g19) halo(C1-C6)alkylthio; (g20) halo(C1-C6)alkylsulfinyl; (g21) halo(C1-C6)alkylsulfonyl; (g22) a substituted (C3-C6)cycloalkyl group having 1 to 3 substituents on the ring, each independently selected from the group consisting of cyano, (C1-C6)alkyl, halo(C1-C6)alkyl, (C1-C6)alkoxy and (C1-C6)alkylcarbonyl; (g23) (C1-C6) alkoxy (C1-C6) alkyl; (g24) (C1-C6) alkoxy (C1-C6) alkoxy; (g25) (C1-C6) alkylcarbonylamino; (g26) halo(C1-C6)alkylcarbonylamino; (g27) (C1-C6) alkylsulfonylamino; (g28) halo(C1-C6)alkylsulfonylamino; (g29) (C1-C6) alkoxycarbonyl; (g30) N-(C1-C6)alkylaminocarbonyl; (g31) N,N-di(C1-C6)alkylaminocarbonyl; (g32) N-halo(C1-C6)alkylaminocarbonyl; (g33) N-(C1-C6)alkylaminosulfonyl; (g34) N,N-di(C1-C6)alkylaminosulfonyl; (g35) furanyl; (g36) a substituted furanyl group having 1 to 3 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (g37) oxazolyl; (g38) a substituted oxazolyl group having 1 to 2 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (g39) isoxazolyl; (g40) a substituted isoxazolyl group having 1 to 2 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (g41) oxadiazolyl; (g42) a substituted oxadiazolyl group having on the ring at least one substituent independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a halo-substituted (C1-C6) alkyl group, and a halo-substituted (C1-C6) alkoxy group; (g43) thienyl; (g44) a substituted thienyl group having 1 to 3 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a halo-substituted (C1-C6) alkyl group and a halo-substituted (C1-C6) alkoxy group; (g45) thiazolyl; (g46) a substituted thiazolyl group having 1 to 2 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (g47) isothiazolyl; (g48) a substituted isothiazolyl group having 1 to 2 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (g49) thiadiazolyl; (g50) a substituted thiadiazolyl group having on the ring one substituent each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (g51) pyrrolyl; (g52) a substituted pyrrolyl group having 1 to 3 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (g53) pyrazolyl; (g54) a substituted pyrazolyl group having 1 to 2 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (g55) imidazolyl; (g56) a substituted imidazolyl group having 1 to 2 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (g57) triazolyl; (g58) a substituted triazolyl group having on the ring one substituent each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (g59) tetrazolyl; (g60) a substituted tetrazolyl group having on the ring one substituent each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (g61) oxazolinyl; (g62) a substituted oxazolinyl group having 1 to 4 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (g63) thiazolyl; (g64) a substituted thiazolyl group having 1 to 4 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (g65) isoxazolinyl; (g66) a substituted isoxazolinyl group having 1 to 4 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (g67) isothiazolyl; (g68) a substituted isothiazolyl group having 1 to 4 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (g69) pyrrolidinyl; (g70) a substituted pyrrolidinyl group having 1 to 4 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (g71) imidazoline; (g72) a substituted imidazolinyl group having 1 to 4 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (g73) phenyl; (g74) a substituted phenyl group having 1 to 5 substituents on the ring, each of which is independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a halo-substituted (C1-C6) alkyl group and a halo-substituted (C1-C6) alkoxy group; (g75) pyridyl; (g76) a substituted pyridyl group having 1 to 4 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (g77) pyridazinyl; (g78) a substituted pyridazinyl group having 1 to 3 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (g79)pyrimidinyl; (g80) a substituted pyrimidinyl group having 1 to 3 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (g81) pyrazinyl; (g82) a substituted pyrazinyl group having 1 to 3 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (g83) triazine group; (g84) a substituted triazine group having 1 to 2 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (g85) dihydrofuranyl; (g86) dihydropyranyl; (g87) phenyloxy; (g88) a substituted phenyloxy group having 1 to 5 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (g89)phenyl(C1-C6)alkoxy; (g90) a substituted phenyl (C1-C6) alkoxy group having 1 to 5 substituents each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo (C1-C6) alkyl group and a halo (C1-C6) alkoxy group on the ring; (g91) a methylenedioxy group formed by two adjacent substituents taken together and which may be substituted by 1 to 2 substituents selected from the group consisting of a halogen atom, a phenyl group and a (C1-C6) alkyl group; and (g92)R 4 -(R 5 -N=)O=S group (where R 4 represents (C1-C6)alkyl, (C3-C6)cycloalkyl, halogenated (C1-C6)alkyl or (C1-C6)alkoxy (C1-C6)alkyl; R 5 represents a hydrogen atom, a cyano group, a (C1-C6)alkyl group, a (C3-C6)cycloalkyl group, a halogenated (C1-C6)alkyl group, a (C1-C6)alkylcarbonyl group or a halogenated (C1-C6)alkylcarbonyl group). Substituent group E includes: (h1) halogen atom; (h2) cyano; (h3) nitro; (h4) amino group; (h5) hydroxyl group; (h6) carboxyl; (h7) (C1-C6) alkyl; (h8) (C1-C6) alkoxy; (h9)(C3-C6)cycloalkyl; (h10)(C1-C6)alkylthio; (h11)(C1-C6)alkylsulfinyl; (h12) (C1-C6) alkylsulfonyl; (h13) halo(C1-C6)alkyl; (h14) halo(C1-C6)alkoxy; (h15) halo(C3-C6)cycloalkyl; (h16) halo(C1-C6)alkylthio; (h17) halo(C1-C6)alkylsulfinyl; (h18) halo(C1-C6)alkylsulfonyl; (h19) (C1-C6) alkoxycarbonyl; (h20)phenyl(C1-C6)alkoxycarbonyl; (h21) (C1-C6) alkylaminocarbonyl; (h22) N-halo(C1-C6)alkylaminocarbonyl; (h23) phenyl; (h24) a substituted phenyl group having 1 to 5 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (h25) a methylenedioxy group formed by two adjacent substituents together, which may be substituted by 1 to 2 substituents selected from the group consisting of a halogen atom and a (C1-C6) alkyl group; (h26)(C1-C6)alkylsulfonylamino; (h27) (C1-C6) alkylaminosulfonyl; (h28) (C1-C6) alkylcarbonylamino; (h29) phenoxy; (h30) a substituted phenoxy group having 1 to 5 substituents each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group on the ring; and (h31)SF5 group. Among them, R 1The (a61) substituted aryl group and the (a63) substituted 5- to 10-membered heterocyclic group do not have a (C1-C6) alkylsulfonyl group, a halogenated (C1-C6) alkylsulfonyl group, an N-(C1-C6) alkylaminosulfonyl group, an N,N-di(C1-C6) alkylaminosulfonyl group, or an R 4 -(R 5 -N=)O=S group (where R 4 represents (C1-C6)alkyl, (C3-C6)cycloalkyl, halogenated (C1-C6)alkyl or (C1-C6)alkoxy (C1-C6)alkyl; R 5 represents a hydrogen atom, a cyano group, a (C1-C6) alkyl group, a (C3-C6) cycloalkyl group, a halogenated (C1-C6) alkyl group, a (C1-C6) alkylcarbonyl group or a halogenated (C1-C6) alkylcarbonyl group).}, The compounds do not include compounds represented by the following structural formula: [Chemical formula 2]

[0007] [2] The compound and salt thereof according to [1], wherein R 1 for (a3) (C2-C6) alkynyl; (a9) a substituted (C1-C6)alkyl group having 1 to 3 substituents each independently selected from Substituent Group A; (a11) phenyl(C1-C6)alkyl (excluding phenylmethyl); (a12) a substituted phenyl (C1-C6) alkyl group having 1 to 5 substituents each independently selected from Substituent Group C on the ring; (a13) pyridyl(C1-C6)alkyl; (a14) a substituted pyridyl(C1-C6)alkyl group having 1 to 4 substituents independently selected from Substituent Group C on the ring; (a15) (C1-C6) alkylcarbonyl; (a16) halo(C1-C6)alkylcarbonyl; (a17) a substituted (C1-C6)alkylcarbonyl group having 1 to 3 substituents each independently selected from Substituent Group A; (a18) phenylcarbonyl; (a19) a substituted phenylcarbonyl group having 1 to 5 substituents each independently selected from Substituent Group C on the ring; (a20) pyridylcarbonyl; (a21) a substituted pyridylcarbonyl group having 1 to 4 substituents each independently selected from Substituent Group C on the ring; (a22) furanylcarbonyl; (a23) a substituted furanylcarbonyl group having 1 to 3 substituents each independently selected from Substituent Group C on the ring; (a24) thienylcarbonyl; (a25) a substituted thienylcarbonyl group having 1 to 3 substituents each independently selected from Substituent Group C on the ring; (a26) pyrazolylcarbonyl; (a27) a substituted pyrazolylcarbonyl group having 1 to 3 substituents each independently selected from Substituent Group C on the ring; (a28) triazolylcarbonyl; (a29) a substituted triazolylcarbonyl group having 1 to 2 substituents each independently selected from Substituent Group C on the ring; (a30) dioxodihydrodibenzofuranylcarbonyl; (a31) a substituted dioxodihydrodibenzofuranylcarbonyl group having 1 to 3 substituents each independently selected from Substituent Group C on its ring; (a32) dihydrobenzodioxinylcarbonyl; (a33) a substituted dihydrobenzodioxinylcarbonyl group having 1 to 7 substituents each independently selected from Substituent Group C on its ring; (a34) (C1-C6) alkoxycarbonyl; (a37) phenyl(C1-C6)alkoxycarbonyl; (a38) a substituted phenyl(C1-C6)alkoxycarbonyl group having 1 to 5 substituents each independently selected from Substituent Group C; (a39) (C1-C6) alkylsulfonyl; (a40) (C3-C6) cycloalkylsulfonyl; (a41) halo(C1-C6)alkylsulfonyl; (a43) a substituted (C1-C6)alkylsulfonyl group having 1 to 3 substituents each independently selected from Substituent Group A; (a45) halo(C1-C6)alkoxyhalo(C1-C6)alkylsulfonyl; (a46) phenylsulfonyl; (a47) a substituted phenylsulfonyl group having 1 to 5 substituents each independently selected from Substituent Group C; (a48) thienylsulfonyl; (a49) a substituted thienylsulfonyl group having 1 to 3 substituents each independently selected from Substituent Group C on the ring; (a50) pyrazolylsulfonyl; (a51) a substituted pyrazolylsulfonyl group having 1 to 3 substituents each independently selected from Substituent Group C on the ring; (a52) thiazolylsulfonyl; (a53) a substituted thiazolylsulfonyl group having 1 to 2 substituents each independently selected from Substituent Group C on the ring; (a54) isoxazolylsulfonyl; (a55) a substituted isoxazolylsulfonyl group having 1 to 2 substituents each independently selected from Substituent Group C on the ring; (a56) quinolylsulfonyl; (a57) a substituted quinolylsulfonyl group having 1 to 6 substituents each independently selected from Substituent Group C on the ring; (a58) phenyl(C1-C6)alkylsulfonyl; (a59) a substituted phenyl (C1-C6) alkylsulfonyl group having 1 to 5 substituents each independently selected from Substituent Group C; (a64) (C3-C6) cycloalkylcarbonyl; (a65) a substituted (C3-C6)cycloalkylcarbonyl group having 1 to 3 substituents each independently selected from Substituent Group B; (a66) isoxazolylcarbonyl; (a67) a substituted isoxazolylcarbonyl group having 1 to 2 substituents each independently selected from Substituent Group C on the ring; (a68) phenylaminocarbonyl; (a69) a substituted phenylaminocarbonyl group having 1 to 5 substituents each independently selected from Substituent Group C on the ring; (a70) pyrimidinylcarbonyl; (a71) a substituted pyrimidinylcarbonyl group having 1 to 3 substituents each independently selected from Substituent Group C on the ring; (a72) pyrazinylcarbonyl; (a73) a substituted pyrazinylcarbonyl group having 1 to 3 substituents each independently selected from Substituent Group C on the ring; (a74) pyridazinylcarbonyl; (a75) a substituted pyridazinylcarbonyl group having 1 to 3 substituents each independently selected from Substituent Group C on the ring; (a76) naphthylcarbonyl; (a77) a substituted naphthylcarbonyl group having 1 to 7 substituents each independently selected from Substituent Group C on the ring; (a78) quinolylcarbonyl; (a79) a substituted quinolylcarbonyl group having 1 to 6 substituents each independently selected from Substituent Group C on its ring; (a80) phenyl; (a81) a substituted phenyl group having 1 to 5 substituents each independently selected from the substituent group D on the ring; (a82) pyridyl; (a83) a substituted pyridyl group having 1 to 4 substituents each independently selected from the substituent group D on the ring; (a84) pyridazinyl; (a85) a substituted pyridazinyl group having 1 to 3 substituents each independently selected from the substituent group D on the ring; (a86) pyrimidinyl; (a87) a substituted pyrimidinyl group having 1 to 3 substituents each independently selected from the substituent group D on the ring; (a88) pyrazinyl; (a89) a substituted pyrazinyl group having 1 to 3 substituents each independently selected from the substituent group D on the ring; (a90) furanyl; (a91) a substituted furanyl group having 1 to 3 substituents each independently selected from Substituent Group D on the ring; (a92) oxazolyl; (a93) substituted oxazolyl having 1 to 2 substituents each independently selected from Substituent Group D on the ring; (a94) oxadiazolyl; (a95) a substituted oxadiazolyl group having on its ring 1 substituent each independently selected from Substituent Group D; (a96) thienyl; (a97) a substituted thienyl group having 1 to 3 substituents each independently selected from the substituent group D on the ring; (a98) thiazolyl; (a99) a substituted thiazolyl group having 1 to 2 substituents each independently selected from the substituent group D on the ring; (a100) thiadiazolyl; (a101) a substituted thiadiazolyl group having on its ring at least one substituent independently selected from the substituent group D; (a102) pyrazolyl; (a103) a substituted pyrazolyl group having 1 to 3 substituents each independently selected from the substituent group D on the ring; (a104) imidazolyl; (a105) a substituted imidazolyl group having 1 to 3 substituents each independently selected from the substituent group D on the ring; (a106) triazolyl; (a107) a substituted triazole group having 1 to 2 substituents each independently selected from the substituent group D on the ring; (a108) tetrazolyl; (a109) a substituted tetrazolyl group having on its ring 1 substituent each independently selected from the substituent group D; (a110) benzoxazolyl; (a111) a substituted benzoxazolyl group having 1 to 4 substituents independently selected from the substituent group D on the ring; (a112) a benzothiazolyl group; (a113) a substituted benzothiazolyl group having 1 to 4 substituents independently selected from the substituent group D on the ring; (a114) a thiazolopyridinyl group; (a115) a substituted thiazolopyridinyl group having 1 to 4 substituents independently selected from the substituent group D on the ring; (a116) a quinoxalinyl group; or (a117) a substituted quinoxalinyl group having 1 to 5 substituents each independently selected from the substituent group D on the ring, R 2 for (b2) (C1-C6) alkyl; (b5) (C3-C6) cycloalkyl; (b10) a substituted (C1-C6)alkyl group having 1 to 3 substituents each independently selected from Substituent Group A; (b20) phenyl; (b21) a substituted phenyl group having 1 to 5 substituents independently selected from the substituent group E on the ring; (b22) pyridyl; (b23) a substituted pyridyl group having 1 to 4 substituents independently selected from the substituent group E on the ring; (b24) pyridazinyl; (b25) a substituted pyridazinyl group having 1 to 3 substituents each independently selected from Substituent Group E on the ring; (b26) pyrimidinyl; (b27) a substituted pyrimidinyl group having 1 to 3 substituents each independently selected from Substituent Group E on the ring; (b28) pyrazinyl; (b29) a substituted pyrazinyl group having 1 to 3 substituents each independently selected from Substituent Group E on the ring; (b34) oxazolyl; (b35) substituted oxazolyl having 1 to 2 substituents independently selected from Substituent Group E on the ring; (b36) isoxazolyl; (b37) a substituted isoxazolyl group having 1 to 2 substituents each independently selected from Substituent Group E on the ring; (b40) thiazolyl; (b41) a substituted thiazolyl group having 1 to 2 substituents each independently selected from the substituent group E on the ring; (b46) pyrazolyl; (b47) a substituted pyrazolyl group having 1 to 3 substituents each independently selected from Substituent Group E on the ring; (b56)quinolinyl; (b57) a substituted quinolyl group having 1 to 6 substituents each independently selected from Substituent Group E on the ring; (b62) phenyl(C1-C6)alkyl; (b63) substituted phenyl (C1-C6) alkyl having 1 to 5 substituents independently selected from Substituent Group E on the ring; (b70) furanyl (C1-C6) alkyl; (b71) a substituted furanyl (C1-C6) alkyl group having 1 to 3 substituents each independently selected from Substituent Group E on the ring; (b72) thienyl(C1-C6)alkyl; (b73) a substituted thienyl(C1-C6)alkyl group having 1 to 3 substituents independently selected from Substituent Group E on the ring; (b74) tetrahydrofuranyl (C1-C6) alkyl; (b75) a substituted tetrahydrofuranyl (C1-C6) alkyl group having 1 to 3 substituents each independently selected from Substituent Group E on the ring; (b76) benzimidazolyl; or (b77) a substituted benzimidazolyl group having 1 to 5 substituents each independently selected from Substituent Group E on the ring, R 3 for (c1) hydrogen atom; (c2) (C1-C6) alkyl; or (c3)(C3-C6)cycloalkyl, R 2 and R 3 can bond to each other to form a ring, X is CH2 or an oxygen atom, Y is an oxygen atom or a sulfur atom, Substituent group A includes: (d1) cyano; (d5) (C3-C6) cycloalkyl; (d6) (C1-C6) alkoxy; (d7) (C1-C6) alkylthio; (d16) phenylthio; (d18) morpholinyl; (d19) phenylcarbonyl; (d20) a substituted phenylcarbonyl group having 1 to 5 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (d21) pyrazolyl; (d22) a substituted pyrazolyl group having 1 to 3 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (d23) thienyl; and (d24) a substituted thienyl group having 1 to 3 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group on the ring, Substituent Group B includes: (e1) cyano; (e2) (C1-C6) alkyl; and (e10) halogenated (C1-C6) alkyl, Substituent group C includes: (f1) halogen atom; (f2) cyano; (f3) nitro; (f6) (C1-C6) alkyl; (f9) (C1-C6) alkoxy; (f10) (C3-C6) cycloalkyl; (f11) (C1-C6) alkylthio; (f12) (C1-C6) alkylsulfinyl; (f13) (C1-C6) alkylsulfonyl; (f14) halo(C1-C6)alkyl; (f17) halogenated (C1-C6) alkoxy; (f19) halo(C1-C6)alkylthio; (f23) (C1-C6) alkoxycarbonyl; (f24) phenyl; (f25) a substituted phenyl group having 1 to 5 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (f26) phenoxy; (f27) a substituted phenoxy group having 1 to 5 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (f28) a methylenedioxy group formed by two adjacent substituents together, which may be substituted by 1 to 2 substituents selected from the group consisting of a halogen atom, a phenyl group and a (C1-C6) alkyl group; (f29) (C1-C6) alkylcarbonylamino; (f30) halo(C1-C6)alkylcarbonylamino; and (f31) (C1-C6)alkylthio (C1-C6)alkylaminocarbonyl, Substituent group D includes: (g1) a halogen atom; (g2) cyano; (g6) (C1-C6) alkyl; (g9) (C1-C6) alkoxy; (g11)(C1-C6)alkylthio; (g14) halo(C1-C6)alkyl; (g17) halogenated (C1-C6) alkoxy; (g19) halo(C1-C6)alkylthio; (g29) (C1-C6) alkoxycarbonyl; (g73) phenyl; and (g74) a substituted phenyl group having 1 to 5 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a halo-substituted (C1-C6) alkyl group and a halo-substituted (C1-C6) alkoxy group on the ring, Substituent group E includes: (h1) halogen atom; (h2) cyano; (h3) nitro; (h7) (C1-C6) alkyl; (h8) (C1-C6) alkoxy; (h9)(C3-C6)cycloalkyl; (h10)(C1-C6)alkylthio; (h12) (C1-C6) alkylsulfonyl; (h13) halo(C1-C6)alkyl; (h14) halo(C1-C6)alkoxy; (h16) halo(C1-C6)alkylthio; (h17) halo(C1-C6)alkylsulfinyl; (h19) (C1-C6) alkoxycarbonyl; (h21) (C1-C6) alkylaminocarbonyl; (h22) N-halo(C1-C6)alkylaminocarbonyl; (h23) phenyl; (h24) a substituted phenyl group having 1 to 5 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (h25) a methylenedioxy group formed by two adjacent substituents together, which may be substituted by 1 to 2 substituents selected from the group consisting of a halogen atom and a (C1-C6) alkyl group; (h26)(C1-C6)alkylsulfonylamino; (h27) (C1-C6) alkylaminosulfonyl; (h28) (C1-C6) alkylcarbonylamino; (h29) phenoxy; (h30) a substituted phenoxy group having 1 to 5 substituents each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group on the ring; and (h31)SF5 group.

[0008] [3] The compound or salt thereof according to [1] or [2], wherein R 1 for (a3) (C2-C6) alkynyl; (a9) a substituted (C1-C6)alkyl group having 1 to 3 substituents each independently selected from Substituent Group A; (a11) phenyl(C1-C6)alkyl (excluding phenylmethyl); (a12) a substituted phenyl (C1-C6) alkyl group having 1 to 5 substituents each independently selected from Substituent Group C on the ring; (a13) pyridyl(C1-C6)alkyl; (a14) a substituted pyridyl(C1-C6)alkyl group having 1 to 4 substituents independently selected from Substituent Group C on the ring; (a16) halo(C1-C6)alkylcarbonyl; (a17) a substituted (C1-C6)alkylcarbonyl group having 1 to 3 substituents each independently selected from Substituent Group A; (a18) phenylcarbonyl; (a19) a substituted phenylcarbonyl group having 1 to 5 substituents each independently selected from Substituent Group C on the ring; (a21) a substituted pyridylcarbonyl group having 1 to 4 substituents each independently selected from Substituent Group C on the ring; (a22) furanylcarbonyl; (a24) thienylcarbonyl; (a34) (C1-C6) alkoxycarbonyl; (a37) phenyl(C1-C6)alkoxycarbonyl; (a39) (C1-C6) alkylsulfonyl; (a40) (C3-C6) cycloalkylsulfonyl; (a41) halo(C1-C6)alkylsulfonyl; (a43) a substituted (C1-C6)alkylsulfonyl group having 1 to 3 substituents each independently selected from Substituent Group A; (a46) phenylsulfonyl; (a47) a substituted phenylsulfonyl group having 1 to 5 substituents each independently selected from Substituent Group C; (a51) a substituted pyrazolylsulfonyl group having 1 to 3 substituents each independently selected from Substituent Group C on the ring; (a56) quinolylsulfonyl; (a58) phenyl(C1-C6)alkylsulfonyl; (a59) a substituted phenyl (C1-C6) alkylsulfonyl group having 1 to 5 substituents each independently selected from Substituent Group C; (a64) (C3-C6) cycloalkylcarbonyl; (a67) a substituted isoxazolylcarbonyl group having 1 to 2 substituents each independently selected from Substituent Group C on the ring; (a69) a substituted phenylaminocarbonyl group having 1 to 5 substituents each independently selected from Substituent Group C on the ring; (a71) a substituted pyrimidinylcarbonyl group having 1 to 3 substituents each independently selected from Substituent Group C on the ring; (a73) a substituted pyrazinylcarbonyl group having 1 to 3 substituents each independently selected from Substituent Group C on the ring; (a75) a substituted pyridazinylcarbonyl group having 1 to 3 substituents each independently selected from Substituent Group C on the ring; (a76) naphthylcarbonyl; (a78) quinolylcarbonyl; (a80) phenyl; (a81) a substituted phenyl group having 1 to 5 substituents each independently selected from the substituent group D on the ring; (a82) pyridyl; (a83) a substituted pyridyl group having 1 to 4 substituents each independently selected from the substituent group D on the ring; (a84) pyridazinyl; (a85) a substituted pyridazinyl group having 1 to 3 substituents each independently selected from the substituent group D on the ring; (a86) pyrimidinyl; (a87) a substituted pyrimidinyl group having 1 to 3 substituents each independently selected from the substituent group D on the ring; (a88) pyrazinyl; (a89) a substituted pyrazinyl group having 1 to 3 substituents each independently selected from the substituent group D on the ring; (a92) oxazolyl; (a93) substituted oxazolyl having 1 to 2 substituents each independently selected from Substituent Group D on the ring; (a96) thienyl; (a97) a substituted thienyl group having 1 to 3 substituents each independently selected from the substituent group D on the ring; (a98) thiazolyl; (a99) a substituted thiazolyl group having 1 to 2 substituents each independently selected from the substituent group D on the ring; (a100) thiadiazolyl; (a101) a substituted thiadiazolyl group having on its ring at least one substituent independently selected from the substituent group D; (a102) pyrazolyl; (a103) a substituted pyrazolyl group having 1 to 3 substituents each independently selected from the substituent group D on the ring; (a108) tetrazolyl; (a109) a substituted tetrazolyl group having on its ring 1 substituent each independently selected from the substituent group D; (a110) benzoxazolyl; (a111) a substituted benzoxazolyl group having 1 to 4 substituents each independently selected from the substituent group D on the ring; (a112) benzothiazolyl; (a113) a substituted benzothiazolyl group having 1 to 4 substituents each independently selected from the substituent group D on the ring; (a114) thiazolopyridinyl; (a115) a substituted thiazolopyridinyl group having 1 to 4 substituents each independently selected from the substituent group D on the ring; (a116) quinoxalinyl; or (a117) a substituted quinoxalinyl group having 1 to 5 substituents each independently selected from the substituent group D on the ring, R 2 for (b2) (C1-C6) alkyl; (b5) (C3-C6) cycloalkyl; (b20) phenyl; (b21) a substituted phenyl group having 1 to 5 substituents independently selected from the substituent group E on the ring; (b22) pyridyl; (b23) a substituted pyridyl group having 1 to 4 substituents independently selected from the substituent group E on the ring; (b24) pyridazinyl; (b25) a substituted pyridazinyl group having 1 to 3 substituents each independently selected from Substituent Group E on the ring; (b26) pyrimidinyl; (b27) a substituted pyrimidinyl group having 1 to 3 substituents each independently selected from Substituent Group E on the ring; (b28) pyrazinyl; (b29) a substituted pyrazinyl group having 1 to 3 substituents each independently selected from Substituent Group E on the ring; (b34) oxazolyl; (b37) a substituted isoxazolyl group having 1 to 2 substituents each independently selected from Substituent Group E on the ring; (b40) thiazolyl; (b41) a substituted thiazolyl group having 1 to 2 substituents each independently selected from the substituent group E on the ring; (b46) pyrazolyl; (b47) a substituted pyrazolyl group having 1 to 3 substituents each independently selected from Substituent Group E on the ring; (b56)quinolinyl; (b57) a substituted quinolyl group having 1 to 6 substituents each independently selected from Substituent Group E on the ring; (b62) phenyl(C1-C6)alkyl; (b63) substituted phenyl (C1-C6) alkyl having 1 to 5 substituents independently selected from Substituent Group E on the ring; (b70) furanyl (C1-C6) alkyl; (b71) a substituted furanyl (C1-C6) alkyl group having 1 to 3 substituents each independently selected from Substituent Group E on the ring; (b72) thienyl(C1-C6)alkyl; (b73) a substituted thienyl(C1-C6)alkyl group having 1 to 3 substituents independently selected from Substituent Group E on the ring; (b74) tetrahydrofuranyl (C1-C6) alkyl; (b75) a substituted tetrahydrofuranyl (C1-C6) alkyl group having 1 to 3 substituents each independently selected from Substituent Group E on the ring; (b76) benzimidazolyl; or (b77) a substituted benzimidazolyl group having 1 to 5 substituents each independently selected from Substituent Group E on the ring, R 3 for (c1) hydrogen atoms, X is CH2 or an oxygen atom, Y is an oxygen atom or a sulfur atom, Substituent group A includes: (d1) cyano; (d6) (C1-C6) alkoxy; (d7) (C1-C6) alkylthio; (d16) phenylthio; (d18) morpholinyl; (d20) a substituted phenylcarbonyl group having 1 to 5 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (d21) pyrazolyl; (d22) a substituted pyrazolyl group having 1 to 3 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; and (d23) thienyl, Substituent group C includes: (f1) halogen atom; (f2) cyano; (f3) nitro; (f6) (C1-C6) alkyl; (f9) (C1-C6) alkoxy; (f10) (C3-C6) cycloalkyl; (f11) (C1-C6) alkylthio; (f12) (C1-C6) alkylsulfinyl; (f13) (C1-C6) alkylsulfonyl; (f14) halo(C1-C6)alkyl; (f17) halogenated (C1-C6) alkoxy; (f19) halo(C1-C6)alkylthio; (f23) (C1-C6) alkoxycarbonyl; (f24) phenyl; (f25) a substituted phenyl group having 1 to 5 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (f26) phenoxy; (f27) a substituted phenoxy group having 1 to 5 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (f28) a methylenedioxy group formed by two adjacent substituents together, which may be substituted by 1 to 2 substituents selected from the group consisting of a halogen atom, a phenyl group and a (C1-C6) alkyl group; (f29) (C1-C6) alkylcarbonylamino group; and (f31) (C1-C6)alkylthio (C1-C6)alkylaminocarbonyl, Substituent group D includes: (g1) a halogen atom; (g2) cyano; (g6) (C1-C6) alkyl; (g9) (C1-C6) alkoxy; (g14) halo(C1-C6)alkyl; (g19) halo(C1-C6)alkylthio; (g29) (C1-C6) alkoxycarbonyl; (g73) phenyl; and (g74) a substituted phenyl group having 1 to 5 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a halo-substituted (C1-C6) alkyl group and a halo-substituted (C1-C6) alkoxy group on the ring, Substituent group E includes: (h1) halogen atom; (h2) cyano; (h3) nitro; (h7) (C1-C6) alkyl; (h8) (C1-C6) alkoxy; (h9)(C3-C6)cycloalkyl; (h10)(C1-C6)alkylthio; (h12) (C1-C6) alkylsulfonyl; (h13) halo(C1-C6)alkyl; (h14) halo(C1-C6)alkoxy; (h16) halo(C1-C6)alkylthio; (h17) halo(C1-C6)alkylsulfinyl; (h19) (C1-C6) alkoxycarbonyl; (h22) N-halo(C1-C6)alkylaminocarbonyl; (h23) phenyl; (h25) a methylenedioxy group formed by two adjacent substituents together, which may be substituted by 1 to 2 substituents selected from the group consisting of a halogen atom and a (C1-C6) alkyl group; (h26)(C1-C6)alkylsulfonylamino; (h27) (C1-C6) alkylaminosulfonyl; (h28) (C1-C6) alkylcarbonylamino; (h29) phenoxy; and (h31)SF5 group.

[0009] [4] A pest control agent comprising the compound or salt thereof according to any one of [1] to [3] as an active ingredient. [5] An agricultural and horticultural pest control agent, characterized in that it contains the compound or salt thereof according to any one of [1] to [3] as an active ingredient. [6] An external parasite control agent for animals, characterized in that it contains the compound or salt thereof according to any one of [1] to [3] as an active ingredient. [7] An internal parasite control agent for animals, characterized in that it contains the compound or salt thereof according to any one of [1] to [3] as an active ingredient. [8] A method for controlling agricultural and horticultural pests, characterized in that plants or soil are treated with an effective amount of the agricultural and horticultural pest control agent according to [5]. [9] A method for controlling external parasites in animals, characterized by orally or parenterally administering an effective amount of the external parasite control agent for animals described in [6] to the target animal.

[10] A method for controlling internal parasites in animals, characterized in that an effective amount of the internal parasite control agent for animals according to [7] is orally or parenterally administered to the target animal.

[11] Use of the compound or salt thereof according to any one of [1] to [3] as a pest control agent. Effects of the Invention

[0010] The compound of the present invention or its salt provides a piperidone derivative represented by the general formula (1) having excellent effects as a pest control agent. DETAILED DESCRIPTION

[0011] In the definition of the general formula (1) of the compound of the present invention, "halo" means a "halogen atom", which means a chlorine atom, a bromine atom, an iodine atom or a fluorine atom.

[0012] “(C1-C6)alkyl” refers to a linear or branched alkyl group having 1 to 6 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, tert-pentyl, neopentyl, 2,3-dimethylpropyl, 1-ethylpropyl, 1-methylbutyl, 2-methylbutyl, n-hexyl, isohexyl, 2-hexyl, 3-hexyl, 2-methylpentyl, 3-methylpentyl, 1,1,2-trimethylpropyl, and 3,3-dimethylbutyl.

[0013] “(C2-C6)alkenyl” means a linear or branched alkenyl group having 2 to 6 carbon atoms, such as vinyl, allyl, isopropenyl, 1-butenyl, 2-butenyl, 2-methyl-2-propenyl, 1-methyl-2-propenyl, 2-methyl-1-propenyl, pentenyl, 1-hexenyl, 3,3-dimethyl-1-butenyl, and the like; and “(C2-C6)alkynyl” means a linear or branched alkynyl group having 2 to 6 carbon atoms, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 3-methyl-1-propynyl, 2-methyl-3-propynyl, pentynyl, 1-hexynyl, 3-methyl-1-butynyl, 3,3-dimethyl-1-butynyl, and the like.

[0014] “(C3-C6) cycloalkyl” refers to a cyclic alkyl group having 3 to 6 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl; and “(C1-C6) alkoxy” refers to a linear or branched alkoxy group having 1 to 6 carbon atoms, such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, tert-butoxy, n-pentoxy, isopentoxy, tert-pentoxy, neopentoxy, 2,3-dimethylpropoxy, 1-ethylpropoxy, 1-methylbutoxy, n-hexyloxy, isohexyloxy, and 1,1,2-trimethylpropoxy.

[0015] The “(C1-C6)alkylthio group” refers to a linear or branched alkylthio group having 1 to 6 carbon atoms, for example, methylsulfanyl, ethylsulfanyl, n-propylsulfanyl, isopropylsulfanyl, n-butylsulfanyl, sec-butylsulfanyl, tert-butylsulfanyl, n-pentylsulfanyl, isopentylsulfanyl, tert-pentylsulfanyl, neopentylsulfanyl, 2,3-dimethylpropylsulfanyl, 1-ethylpropylsulfanyl, 1-methylbutylsulfanyl, n-hexylsulfanyl, isohexylsulfanyl, 1,1,2-trimethylpropylsulfanyl, and the like.

[0016] The “(C1-C6)alkylsulfinyl group” refers to a linear or branched alkylsulfinyl group having 1 to 6 carbon atoms, for example, methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, sec-butylsulfinyl, tert-butylsulfinyl, n-pentylsulfinyl, isopentylsulfinyl, tert-pentylsulfinyl, neopentylsulfinyl, 2,3-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, 1-methylbutylsulfinyl, n-hexylsulfinyl, isohexylsulfinyl, and 1,1,2-trimethylpropylsulfinyl.

[0017] The “(C1-C6)alkylsulfonyl group” refers to a linear or branched alkylsulfonyl group having 1 to 6 carbon atoms, such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, sec-butylsulfonyl, tert-butylsulfonyl, n-pentylsulfonyl, isopentylsulfonyl, tert-pentylsulfonyl, neopentylsulfonyl, 2,3-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, 1-methylbutylsulfonyl, n-hexylsulfonyl, isohexylsulfonyl and 1,1,2-trimethylpropylsulfonyl.

[0018] “N-(C1-C6)alkylamino” refers to a linear or branched alkylamino group having 1 to 6 carbon atoms, such as N-methylamino, N-ethylamino, N-n-propylamino, N-isopropylamino, N-n-butylamino, N-sec-butylamino, N-tert-butylamino, N-n-pentylamino, N-isopentylamino, N-tert-pentylamino, N-neopentylamino, N-(2,3-dimethylpropyl)amino, N-(1-ethylpropyl)amino, N-(1-methylbutyl)amino, N-n-hexylamino, N-isohexylamino, and N-(1,1,2-trimethylpropyl)amino.

[0019] “N,N-di(C1-C6)alkylamino” refers to, for example, N,N-dimethylamino, N,N-diethylamino, N,N-di-n-propylamino, N,N-diisopropylamino, N,N-di-n-butylamino, N,N-di-sec-butylamino, N,N-di-tert-butylamino, N-methyl-N-ethylamino, N-methyl-N-n-propylamino, N-methyl-N-isopropylamino, N-methyl-N-n-butylamino, N-methyl-N-sec-butylamino, N-methyl-N-tert-butylamino, N-methyl The amino group preferably includes a linear or branched dialkylamino group having 2 to 12 carbon atoms, such as N-methyl-N-n-pentylamino, N-methyl-N-isopentylamino, N-methyl-N-tert-pentylamino, N-methyl-N-neopentylamino, N-methyl-N-(2,3-dimethylpropyl)amino, N-methyl-N-(1-ethylpropyl)amino, N-methyl-N-(1-methylbutyl)amino, N-methyl-N-n-hexylamino, N-methyl-N-isohexylamino and N-methyl-N-(1,1,2-trimethylpropyl)amino.

[0020] The "(C1-C6)alkylcarbonyl group" refers to an alkylcarbonyl group having 2 to 7 carbon atoms, such as acetyl, propionyl, butyryl, 2-methylpropionyl, valeryl, 2-methylbutyryl, 3-methylbutyryl, pivaloyl, hexanoyl, etc., which has the above-mentioned (C1-C6)alkyl group.

[0021] The “(C1-C6)alkylcarbonylamino” refers to an alkylcarbonylamino group having the above-mentioned (C1-C6)alkyl group, such as acetylamino, propionylamino, butyrylamino, 2-methylpropionylamino, valerylamino, 2-methylbutyrylamino, 3-methylbutyrylamino, pivaloylamino, hexanoylamino, etc., and an alkylcarbonylamino group having 2 to 7 carbon atoms.

[0022] The “(C1-C6)alkylsulfonylamino group” refers to a linear or branched alkylsulfonylamino group having 1 to 6 carbon atoms, for example, a methylsulfonylamino group, an ethylsulfonylamino group, an n-propylsulfonylamino group, an isopropylsulfonylamino group, an n-butylsulfonylamino group, a sec-butylsulfonylamino group, a tert-butylsulfonylamino group, an n-pentylsulfonylamino group, an isopentylsulfonylamino group, a tert-pentylsulfonylamino group, a neopentylsulfonylamino group, a 2,3-dimethylpropylsulfonylamino group, a 1-ethylpropylsulfonylamino group, a 1-methylbutylsulfonylamino group, an n-hexylsulfonylamino group, an isohexylsulfonylamino group, and a 1,1,2-trimethylpropylsulfonylamino group.

[0023] “N-(C1-C6)alkylaminocarbonyl” refers to a linear or branched alkylaminocarbonyl group having 2 to 7 carbon atoms and an alkyl group having 1 to 6 carbon atoms, such as N-methylaminocarbonyl, N-ethylaminocarbonyl, N-n-propylaminocarbonyl, N-isopropylaminocarbonyl, N-n-butylaminocarbonyl, N-isobutylaminocarbonyl, N-sec-butylaminocarbonyl, N-tert-butylaminocarbonyl, N-n-pentylaminocarbonyl, N-isopentylaminocarbonyl, N-tert-pentylaminocarbonyl, N-neopentylaminocarbonyl, N-n-hexylaminocarbonyl, and N-isohexylaminocarbonyl.

[0024] “N,N-di(C1-C6)alkylaminocarbonyl” refers to, for example, N,N-dimethylaminocarbonyl, N,N-diethylaminocarbonyl, N,N-di-n-propylaminocarbonyl, N,N-diisopropylaminocarbonyl, N,N-di-n-butylaminocarbonyl, N,N-di-sec-butylaminocarbonyl, N,N-di-tert-butylaminocarbonyl, N-methyl-N-ethylaminocarbonyl, N-methyl-N-n-propylaminocarbonyl, N-methyl-N-isopropylaminocarbonyl, N-methyl-N-n-butylaminocarbonyl, N-methyl-N-sec-butylaminocarbonyl, N-methyl-N-tert-butylaminocarbonyl, N-methyl-N-n-ethylaminocarbonyl, A dialkylaminocarbonyl group having 3 to 13 carbon atoms and having an alkyl group having 1 to 6 carbon atoms, such as a pentylaminocarbonyl group, an N-methyl-N-isopentylaminocarbonyl group, an N-methyl-N-tert-pentylaminocarbonyl group, an N-methyl-N-neopentylaminocarbonyl group, an N-methyl-N-(2,3-dimethyl-propyl)aminocarbonyl group, an N-methyl-N-(1-ethylpropyl)aminocarbonyl group, an N-methyl-N-(1-methyl-butyl)aminocarbonyl group, an N-methyl-N-n-hexylaminocarbonyl group, an N-methyl-N-isohexylaminocarbonyl group and an N-methyl-N-(1,1,2-trimethyl-propyl)aminocarbonyl group.

[0025] The "(C1-C6)alkoxycarbonyl group" refers to an alkoxycarbonyl group having 2 to 7 carbon atoms, such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl, pentyloxycarbonyl, etc., which have the above-mentioned (C1-C6)alkoxy group.

[0026] The “N-(C1-C6)alkylaminosulfonyl group” refers to a linear or branched alkylaminosulfonyl group having 1 to 6 carbon atoms, such as N-methylaminosulfonyl, N-ethylaminosulfonyl, N-n-propylaminosulfonyl, N-isopropylaminosulfonyl, N-n-butylaminosulfonyl, N-sec-butylaminosulfonyl, N-tert-butylaminosulfonyl, N-n-pentylaminosulfonyl, N-isopentylaminosulfonyl, N-tert-pentylaminosulfonyl, N-neopentylaminosulfonyl, N-(2,3-dimethylpropyl)aminosulfonyl, N-(1-ethylpropyl)aminosulfonyl, N-(1-methylbutyl)aminosulfonyl, N-n-hexylaminosulfonyl, N-isohexylaminosulfonyl and N-(1,1,2-trimethylpropyl)aminosulfonyl.

[0027] The “N,N-di(C1-C6)alkylaminosulfonyl group” refers to, for example, N,N-dimethylaminosulfonyl, N,N-diethylaminosulfonyl, N,N-di-n-propylaminosulfonyl, N,N-diisopropylaminosulfonyl, N,N-di-n-butylaminosulfonyl, N,N-di-sec-butylaminosulfonyl, N,N-di-tert-butylaminosulfonyl, N-methyl-N-ethylaminosulfonyl, N-methyl-N-n-propylaminosulfonyl, N-methyl-N-isopropylaminosulfonyl, N-methyl-N-n-butylaminosulfonyl, N-methyl-N-sec-butylaminosulfonyl, N-methyl-N-tert-butylaminosulfonyl. a linear or branched dialkylaminosulfonyl group having 2 to 12 carbon atoms, such as N-methyl-N-n-pentylaminosulfonyl, N-methyl-N-isopentylaminosulfonyl, N-methyl-N-tert-pentylaminosulfonyl, N-methyl-N-neopentylaminosulfonyl, N-methyl-N-(2,3-dimethylpropyl)aminosulfonyl, N-methyl-N-(1-ethylpropyl)aminosulfonyl, N-methyl-N-(1-methylbutyl)aminosulfonyl, N-methyl-N-n-hexylaminosulfonyl, N-methyl-N-isohexylaminosulfonyl and N-methyl-N-(1,1,2-trimethylpropyl)aminosulfonyl.

[0028] In the substitutable positions of the above-mentioned "(C1-C6) alkyl", "(C2-C6) alkenyl", "(C2-C6) alkynyl", "(C1-C6) alkoxy", "(C1-C6) alkylthio", "(C1-C6) alkylsulfinyl", "(C1-C6) alkylsulfonyl", "N-(C1-C6) alkylamino", "N,N-di(C1-C6) alkylamino", "(C3-C6) cycloalkyl", "(C1-C6) alkylcarbonylamino", "(C1-C6) alkylsulfonylamino", "N-(C1-C6) alkylaminocarbonyl", "N,N-di(C1-C6) alkylaminocarbonyl" and the like, 1 or 2 or more halogen atoms may be substituted. When the number of substituted halogen atoms is 2 or more, the halogen atoms may be the same or different.

[0029] They are respectively expressed as "halo(C1-C6)alkyl", "halo(C2-C6)alkenyl", "halo(C2-C6)alkynyl", "halo(C1-C6)alkoxy", "halo(C1-C6)alkylthio", "halo(C1-C6)alkylsulfinyl", "halo(C1-C6)alkylsulfonyl", "N-halo(C1-C6)alkylamino", "N,N-dihalo(C1-C6)alkylamino", "halo(C3-C6)cycloalkyl", "halo(C1-C6)alkylcarbonylamino", "halo(C1-C6)alkylsulfonylamino", "N-halo(C1-C6)alkylaminocarbonyl", "N,N-dihalo(C1-C6)alkylaminocarbonyl", etc.

[0030] Expressions such as "(C1-C6)", "(C2-C6)", and "(C3-C6)" indicate the range of carbon atoms of various substituents. In addition, the above definition can also be expressed for groups formed by connecting the above substituents. For example, in the case of "(C1-C6)alkoxy(C1-C6)alkyl", it means that a linear or branched alkoxy group having 1 to 6 carbon atoms is bonded to a linear or branched alkyl group having 1 to 6 carbon atoms.

[0031] The "aryl group" refers to an aromatic hydrocarbon group having 6 to 10 carbon atoms, such as phenyl, 1-naphthyl, and 2-naphthyl.

[0032] Examples of the "5- to 10-membered heterocyclic group" include a 5- or 6-membered monocyclic aromatic heterocyclic group containing, as ring-constituting atoms in addition to carbon atoms, 1 to 4 heteroatoms selected from oxygen atoms, sulfur atoms and nitrogen atoms, an aromatic condensed heterocyclic group in which the monocyclic aromatic heterocyclic ring is condensed with a benzene ring or a monocyclic aromatic ring, a 4- to 6-membered monocyclic non-aromatic heterocyclic group, or a non-aromatic condensed heterocyclic group in which the monocyclic non-aromatic heterocyclic ring is condensed with a benzene ring or a monocyclic aromatic ring. The ring-constituting atoms of the above 5- to 10-membered heterocyclic group may be oxidized with an oxo group.

[0033] Examples of the “monocyclic aromatic heterocyclic group” include furanyl, thienyl, pyridyl, 2-oxopyridyl, pyrimidyl, pyridazinyl, pyrazinyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, oxadiazolyl (e.g., 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl), thiadiazolyl (e.g., 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl), triazolyl (e.g., 1,2,4-triazolyl), tetrazolyl, triazinyl (e.g., 1,3,5-triazinyl, 1,2,4-triazinyl), Examples of the “aromatic fused heterocyclic group” include quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, cinnolinyl, phthalazinyl, naphthyridinyl, benzofuranyl, benzothiophenyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzisothiazolyl, benzimidazolyl, benzotriazolyl, indolyl, isoindolyl, indazolyl, furopyridyl, thienopyridyl, pyrrolopyridyl (e.g., pyrrolo[1,2-a]pyridyl, pyrrolo[2,3-b]pyridyl), oxazolopyridyl (e.g., oxazolo[3,2-a]pyridyl), pyridyl), isoxazolo[2,3-a]pyridyl, isoxazolo[4,5-b]pyridyl, isoxazolo[5,4-b]pyridyl), thiazolopyridyl (e.g., thiazolopyridyl, thiazolopyridyl, thiazolopyridyl), isothiazolo[2,3-a]pyridyl, isoxazolo[4,5-b]pyridyl, isoxazolo[5,4-b]pyridyl), b]pyridyl), imidazopyridyl (e.g., imidazo[1,2-a]pyridyl, imidazo[4,5-b]pyridyl), pyrazolopyridyl (e.g., pyrazolo[1,5-a]pyridyl, pyrazolo[3,4-a]pyridyl, pyrazolo[4,3-a]pyridyl), indolizinyl, triazolopyridyl (e.g., [1,2,4]triazolo[1,5-a]pyridyl), triazolopyrimidinyl, pyrrolopyrimidinyl, pyrrolopyrazinyl, imidazopyrimidinyl, imidazopyrazinyl, pyrazolopyrimidinyl, pyrazolothienyl, pyrazolotriazinyl, and the like.

[0034] Examples of the “monocyclic non-aromatic heterocyclic group” include an oxetanyl group, a thietanyl group, an azetidinyl group, a pyrrolidinyl group, a pyrrolidinyl-2-one group, a piperidinyl group, a morpholinyl group, a thiomorpholinyl group, a piperazinyl group, a hexamethyleneiminyl group, an oxazolidinyl group, a thiazolidinyl group, an imidazolidinyl group, an oxazolinyl group, a thiazolinyl group, an isoxazolinyl group, an imidazolinyl group, a dioxolyl group, a dioxolanyl group, and a dioxolanyl group. group), dihydrooxadiazolyl, 2-oxo-tetrahydropyrrol-1-yl, 2-oxopyridin-4-yl, 2,4-dioxopyrimidin-5-yl, 2-oxo-1,3-oxazolidin-5-yl, 5-oxo-1,2,4-oxadiazolin-3-yl, 1,3-dioxolan-2-yl, 1,3-dioxan-2-yl, 1,3-dioxepan-2-yl, pyranyl, tetrahydropyranyl, thiopyranyl, tetrahydrothiopyranyl, 1-oxide tetrahydrothiopyranyl, 1,1-dioxide tetrahydro Examples of the “non-aromatic fused heterocyclic group” include thiopyranyl, tetrahydrofuranyl, dioxanyl, pyrazolidinyl, pyrazolinyl, tetrahydropyrimidinyl, dihydrotriazolyl, and tetrahydrotriazolyl. Examples of the “non-aromatic fused heterocyclic group” include dihydroindole, dihydroisoindole, dihydrobenzofuranyl, dihydrobenzodioxinyl, dihydrobenzodioxepinyl, tetrahydrobenzofuranyl, chromenyl group, dihydroquinolinyl, tetrahydroquinolinyl, dihydroisoquinolinyl, tetrahydroisoquinolinyl, and dihydrophthalazinyl.

[0035] R 2 and R 3 They may be bonded to each other to form a ring. Examples of the "ring" include 3-7 membered nitrogen-containing heterocyclic rings such as aziridine, azetidine, pyrrole, piperidine, homopiperidine, piperazine, homopiperazine, morpholine, and homomorpholine. The nitrogen-containing heterocyclic ring may be fused with a benzene ring. The nitrogen-containing heterocyclic ring and the benzene ring may be substituted with 1 to 6 substituents selected from the group consisting of halogen atoms, (C1-C6) alkyl, and (C1-C6) alkyl.

[0036] Examples of salts of the compound represented by the general formula (1) of the present invention include: inorganic acid salts such as hydrochlorides, sulfates, nitrates, and phosphates; organic acid salts such as acetates, fumarates, maleates, oxalates, methanesulfonates, benzenesulfonates, and p-toluenesulfonates; and salts formed with inorganic or organic bases such as sodium ion, potassium ion, calcium ion, and trimethylammonium.

[0037] Regarding the compounds represented by the general formula (1) of the present invention and their salts, there are cases where there are one or more asymmetric centers in their structural formulas, and there are also cases where there are two or more optical isomers and diastereomers. The present invention includes all optical isomers and mixtures thereof in any proportion. In addition, regarding the compounds represented by the general formula (1) of the present invention and their salts, there are also cases where there are two geometric isomers derived from carbon-carbon double bonds in their structural formulas. The present invention includes all geometric isomers and mixtures thereof in any proportion. In addition, there are cases where there are multiple tautomers in the compounds represented by the general formula (1) of the present invention and their salts. The present invention includes all tautomers and mixtures thereof in any proportion.

[0038] Among the compounds represented by the general formula (1) of the present invention, preferred embodiments are shown below. In the general formula (1), R 1, preferably (a3), (a9), (a11), (a12), (a13), (a14), (a15), (a16), (a17), (a18), (a19), (a20), (a21), (a22), (a23), (a24), (a25), (a26), (a27), (a28), (a29), (a30), (a31), (a32), (a33), (a34 ), (a37), (a38), (a39), (a40), (a41), (a43), (a45), (a46), (a47), (a48), (a49), (a50), (a51) , (a52), (a53), (a54), (a55), (a56), (a57), (a58), (a59), (a64), (a65), (a66), (a67), (a68), (a69), (a70), (a71), (a72), (a73), (a74), (a75), (a76), (a77), (a78), (a79), (a80), (a81), (a82), (a83), (a84), (a85), (a86), (a87), (a88), (a89), (a90), (a91), (a92), (a93), (a94), ( a95), (a96), (a97), (a98), (a99), (a100), (a101), (a102), (a103), (a104), (a105), (a106), (a107), (a108), (a109), (a110), (a111), (a112), (a113), (a114), (a115), (a116) or (a117),More preferably, (a3), (a9), (a11), (a12), (a13), (a14), (a16), (a17), (a18), (a19), (a21), (a22), (a24), (a34), (a37), (a39), (a40), (a41), (a43), (a46), (a47), (a51), (a56), (a58), (a59), (a64), (a67), (a69), (a71), (a73), (a75), (a76), (a78 )、(a80)、(a81)、(a82)、(a83)、(a84)、(a85)、(a86)、(a87)、(a88)、(a89)、(a92)、(a93)、(a96)、(a97)、(a98)、(a99)、(a100)、(a101)、(a102)、(a103)、(a108)、(a109)、(a110)、(a111)、(a112)、(a113)、(a114)、(a115)、(a116)、(a117). ,

[0039] In the general formula (1), R 2 , preferably (b2), (b5), (b10), (b20), (b21), (b22), (b23), (b24), (b25), (b26), (b27), (b28), (b29), (b34), (b35), (b36), (b37), (b40), (b41), (b46), (b47), (b62), (b63), (b70), (b71), (b72), (b73), (b74), (b75), (b76) or (b77) Groups, more preferably groups of (b2), (b5), (b20), (b21), (b22), (b23), (b24), (b25), (b26), (b27), (b28), (b29), (b34), (b37), (b40), (b41), (b46), (b47), (b56), (b57), (b62), (b63), (b70), (b71), (b72), (b73), (b74), (b75), (b71) or (b72).

[0040] In the general formula (1), R 3 , preferably the group of (c1), (c2) or (c3) above, more preferably the hydrogen atom of (c1) above.

[0041] In the general formula (1), X is preferably CH2 or an oxygen atom.

[0042] In the general formula (1), Y is preferably an oxygen atom or a sulfur atom.

[0043] In the general formula (1), as the substituent group A, preferably, the groups including the above-mentioned (d1), (d5), (d6), (d7), (d16), (d18), (d19), (d20), (d21), (d22), (d23) and (d24) are included, and the groups including the above-mentioned (d1), (d6), (d7), (d16), (d18), (d20), (d21), (d22) and (d23) are more included.

[0044] In the general formula (1), as the substituent group B, preferably includes the above-mentioned groups (e1), (e2) and (e10).

[0045] In the general formula (1), as the substituent group C, preferably include the groups (f1), (f2), (f3), (f6), (f9), (f10), (f11), (f12), (f13), (f14), (f17), (f19), (f23), (f24), (f25), (f26), (f27), (f28), (f29), (f30) and (f31) above, and more preferably include the groups (f1), (f2), (f3), (f6), (f10), (f11), (f12), (f13), (f14), (f17), (f19), (f23), (f24), (f25), (f26), (f27), (f28), (f29) and (f31) above.

[0046] In the general formula (1), as the substituent group D, preferably includes the groups (g1), (g2), (g6), (g9), (g11), (g14), (g17), (g19), (g29), (g73) and (g74) mentioned above, and more preferably includes the groups (g1), (g2), (g6), (g9), (g14), (g19), (g29), (g73) and (g74) mentioned above.

[0047] In the general formula (1), as the substituent group E, preferably, the groups including the above-mentioned (h1), (h2), (h3), (h7), (h8), (h9), (h10), (h12), (h13), (h14), (h16), (h17), (h19), (h21), (h22), (h23), (h24), (h25), (h26), (h27), (h28), (h29), (h30) and (h31) are included, More preferably, the groups include those described above (h1), (h2), (h3), (h7), (h8), (h9), (h10), (h12), (h13), (h14), (h16), (h17), (h19), (h22), (h23), (h25), (h26), (h27), (h28), (h29) and (h31).

[0048] The various compounds of the present invention can be produced, for example, by the following production methods, but the present invention is not limited thereto.

[0049] Manufacturing method 1 The compound represented by the general formula (1-1) of the present invention can be produced from the compound represented by the general formula (2) by the following step [a]. [Chemical formula 3]

[0050] {In the formula, R 1 , R 2 , X and Y are the same as above.}

[0051] Manufacturing method of step [a] The compound represented by the general formula (1-1) of the present invention can be produced by reacting a compound represented by the general formula (2) with a compound represented by the general formula (4) in the presence of a base and an inert solvent.

[0052] Examples of the base that can be used in the present reaction include hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide; alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide; alkali metal hydrides such as sodium hydride and potassium hydride; carbonates such as lithium carbonate, lithium bicarbonate, sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, calcium carbonate, magnesium carbonate, and cesium carbonate; acetates such as lithium acetate, sodium acetate, and potassium acetate; and organic bases such as pyridine, picoline, lutidine, triethylamine, tributylamine, N,N-diisopropylethylamine, and diazabicycloundecene (DBU). The amount used can be appropriately selected within the usual range of 1 to 10 times the molar amount of the compound represented by the general formula (2).

[0053] As the inactive solvent that can be used in the present reaction, any solvent that does not significantly hinder the progress of the present reaction can be used, for example: chain or cyclic saturated hydrocarbons such as pentane, hexane, and cyclohexane; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; inactive solvents such as chain or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, and tetrahydrofuran; nitriles such as acetonitrile and propionitrile; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, and 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, propanol, butanol, and 2-propanol, etc. These inactive solvents can be used alone or in combination of two or more. The amount used can be appropriately selected within the range of 0.1 to 100 L per mol of the compound represented by the general formula (2).

[0054] This reaction is an equimolar reaction, so each compound can be used in an equimolar manner, or any compound can be used in excess. The reaction temperature in this reaction is usually carried out in the range of about 0°C to the boiling point of the solvent used, and the reaction time varies according to the reaction scale, reaction temperature, etc., and is not constant, and is usually appropriately selected within the range of several minutes to 48 hours. After the reaction is completed, the target product can be separated from the reaction system containing the target product by conventional methods, and the target product can be manufactured by purification using recrystallization, column chromatography, etc. as needed.

[0055] Manufacturing method 2 The compound represented by the general formula (1-2) of the present invention can be produced from the compound represented by the general formula (3) by the following step [b]. [Chemical formula 4]

[0056] {In the formula, R 1 , R 2 , R 3 and Y are the same as above. L represents a halogen atom such as chlorine, bromine, etc.; a leaving group such as (C1-C6) alkoxycarbonyloxy, etc.

[0057] Manufacturing method of step [b] The compound represented by the general formula (1-2) can be produced by reacting a compound represented by the general formula (3) or a salt thereof with a compound represented by the general formula (5) in the presence of an inert solvent and a base.

[0058] Examples of the base that can be used in the present reaction include hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide; alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide; alkali metal hydrides such as sodium hydride and potassium hydride; carbonates such as lithium carbonate, lithium bicarbonate, sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, calcium carbonate, magnesium carbonate, and cesium carbonate; acetates such as lithium acetate, sodium acetate, and potassium acetate; and organic bases such as pyridine, picoline, lutidine, triethylamine, tributylamine, N,N-diisopropylethylamine, and DBU. The amount used can be appropriately selected within the usual range of 1 to 10 times the molar amount of the compound represented by the general formula (3).

[0059] As the inactive solvent that can be used in the present reaction, any solvent that does not significantly hinder the progress of the present reaction can be used, for example: chain or cyclic saturated hydrocarbons such as pentane, hexane, and cyclohexane; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; inactive solvents such as chain or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, and tetrahydrofuran; nitriles such as acetonitrile and propionitrile; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, and 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, propanol, butanol, and 2-propanol, etc. These inactive solvents can be used alone or in combination of two or more. The amount used can be appropriately selected within the range of 0.1 to 100 L per mol of the compound represented by the general formula (3).

[0060] This reaction is an equimolar reaction, so each compound can be used in an equimolar manner, or any compound can be used in excess. The reaction temperature in this reaction is usually carried out in the range of about 0°C to the boiling point of the solvent used, and the reaction time varies according to the reaction scale, reaction temperature, etc., and is not constant, and is usually appropriately selected within the range of several minutes to 48 hours. After the reaction is completed, the target product can be separated from the reaction system containing the target product by conventional methods, and the target product can be manufactured by purification using recrystallization, column chromatography, etc. as needed.

[0061] Manufacturing method 3 The compound represented by the general formula (1-3) of the present invention can be produced by the following step [c] from the compound represented by the general formula (3). [Chemical formula 5]

[0062] {In the formula, R 2 , R 3 and Y are the same as above. L' represents a halogen atom such as chlorine or bromine; a leaving group such as (C1-C6) alkoxycarbonyloxy or (C1-C6) alkylcarbonyloxy.1a represents (C1-C6)alkyl, halogenated (C1-C6)alkyl, substituted (C1-C6)alkyl having 1 to 3 substituents independently selected from Substituent Group A, phenyl, substituted phenyl having 1 to 5 substituents independently selected from Substituent Group C on the ring, pyridyl, substituted pyridyl having 1 to 4 substituents independently selected from Substituent Group C on the ring, furanyl, substituted furanyl having 1 to 3 substituents independently selected from Substituent Group C on the ring, thienyl, substituted thienyl having 1 to 3 substituents independently selected from Substituent Group C on the ring, pyrazolyl, substituted pyrazolyl having 1 to 3 substituents independently selected from Substituent Group C on the ring, triazolyl, substituted triazolyl having 1 to 2 substituents independently selected from Substituent Group C on the ring, dioxadihydrodibenzofuranyl, substituted dioxadihydrodibenzofuranyl having 1 to 3 substituents independently selected from Substituent Group C on the ring, dihydrobenzodioxinyl, substituted dihydrobenzodioxinyl having 1 to 7 substituents independently selected from Substituent Group C on the ring, (C3-C6)cycloalkyl, substituted (C3-C6)cycloalkyl having 1 to 3 substituents independently selected from Substituent Group B, isoxazolyl, or substituted isoxazolyl having 1 to 2 substituents independently selected from Substituent Group C on the ring (Substituent Groups A, B and C are the same as above.).}

[0063] Manufacturing method of step [c] The compound represented by the general formula (1-3) can be produced by condensing the compound represented by the general formula (3) or a salt thereof with the compound represented by the general formula (6) or (7) by an amidation method commonly used in organic synthesis.

[0064] Method for producing starting material 1 Among the compounds represented by the general formula (2) which are the starting materials of the compounds represented by the general formula (1-1) of the present invention, the compound (2-1) in which X is CH2 can be produced by the following production method, i.e., based on the compound represented by the general formula (8) through the following steps [d], [e], [f] and [g]. [Chemical formula 6]

[0065] {In the formula, R 1 Same as above. L represents a leaving group such as a halogen atom such as chlorine or bromine. R' represents a (C1-C6) alkyl group such as methyl or ethyl.

[0066] Manufacturing method of step [d] The compound represented by the general formula (9) can be produced by reacting the compound represented by the general formula (8) with di-tert-butyl ester in the presence or absence of a base and an inert solvent.

[0067] Examples of the base that can be used in the present reaction include hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide; alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide; alkali metal hydrides such as sodium hydride and potassium hydride; carbonates such as lithium carbonate, lithium bicarbonate, sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, calcium carbonate, magnesium carbonate, and cesium carbonate; acetates such as lithium acetate, sodium acetate, and potassium acetate; and organic bases such as pyridine, picoline, lutidine, triethylamine, tributylamine, and N,N-diisopropylethylamine. The amount used can be appropriately selected within the usual range of 1 to 10 times the molar amount of the compound represented by the general formula (8). However, the base can also be used as a solvent.

[0068] As the inactive solvent that can be used in the present reaction, any solvent that does not significantly inhibit the progress of the present reaction can be used, for example: linear or cyclic saturated hydrocarbons such as pentane, hexane, and cyclohexane; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; inactive solvents such as linear or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, and tetrahydrofuran; nitriles such as acetonitrile and propionitrile; esters such as methyl acetate; ketones such as acetone and methyl ethyl ketone; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, and 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, propanol, butanol, and 2-propanol, etc. These inactive solvents can be used alone or in combination of two or more. The amount used may be appropriately selected within the range of usually 0.1 to 100 L per 1 mol of the compound represented by the general formula (8). When the above-mentioned base is used as a solvent, no solvent may be used.

[0069] This reaction is an equimolar reaction, so each compound can be used in an equimolar manner, or any compound can be used in excess. The reaction temperature in this reaction is usually carried out in the range of -100 ° C to the boiling point of the solvent used, and the reaction time varies according to the reaction scale, reaction temperature, etc., and is not constant, and is usually appropriately selected within the range of a few minutes to 48 hours. After the reaction is completed, the target product can be separated from the reaction system containing the target product by a conventional method, and the target product can be manufactured by purification using recrystallization, column chromatography, etc. as needed. In addition, it can also be supplied to the next step without separation.

[0070] Manufacturing method of step [e] The compound represented by the general formula (11) can be produced by reacting the compound represented by the general formula (9) with the compound represented by the general formula (10) in the presence of a base and an inert solvent.

[0071] Examples of the base that can be used in the present reaction include hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide; alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide; alkali metal hydrides such as sodium hydride and potassium hydride; carbonates such as lithium carbonate, lithium bicarbonate, sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, calcium carbonate, magnesium carbonate, and cesium carbonate; acetates such as lithium acetate, sodium acetate, and potassium acetate; and organic bases such as pyridine, picoline, lutidine, triethylamine, tributylamine, and N,N-diisopropylethylamine. The amount used can be appropriately selected within the usual range of 1 to 10 times the molar amount of the compound represented by the general formula (9).

[0072] As the inactive solvent that can be used in the present reaction, any solvent that does not significantly hinder the progress of the present reaction can be used, for example: chain or cyclic saturated hydrocarbons such as pentane, hexane, and cyclohexane; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; inactive solvents such as chain or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, and tetrahydrofuran; nitriles such as acetonitrile and propionitrile; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, and 1,3-dimethyl-2-imidazolidinone, etc. These inactive solvents can be used alone or in combination of two or more. The amount used can be appropriately selected within the range of 0.1 to 100 L per 1 mol of the compound represented by the general formula (9).

[0073] This reaction is an equimolar reaction, so each compound can be used in an equimolar manner, or any compound can be used in excess. The reaction temperature in this reaction is usually carried out in the range of about 0°C to the boiling point of the solvent used, and the reaction time varies according to the reaction scale, reaction temperature, etc., and is not constant, and is usually appropriately selected within the range of a few minutes to 48 hours. After the reaction is completed, the target product can be separated from the reaction system containing the target product by conventional methods, and the target product can be manufactured by purification using recrystallization, column chromatography, etc. as needed. In addition, it can also be supplied to the next step without separation.

[0074] Manufacturing method of step [f] The compound represented by the general formula (12) can be produced by hydrolyzing the compound represented by the general formula (11) in the presence or absence of an acid and an inert solvent.

[0075] Examples of the acid that can be used in the present reaction include inorganic acids such as hydrochloric acid, sulfuric acid, and nitric acid; organic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, and benzoic acid; sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid, and p-toluenesulfonic acid; phosphoric acid, etc. The amount used can be appropriately selected from the range of 0.01 times the mole to 10 times the mole of the compound represented by the general formula (11). The acid can also be used as a solvent.

[0076] As the inactive solvent that can be used in the present reaction, any solvent that does not significantly hinder the progress of the present reaction can be used, for example, aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; chain or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, and tetrahydrofuran; esters such as ethyl acetate; amides such as N,N-dimethylformamide and N,N-dimethylacetamide; ketones such as acetone and methyl ethyl ketone; polar solvents such as dimethyl sulfoxide and 1,3-dimethyl-2-imidazolidinone, etc., and these inactive solvents can be used alone or in combination of two or more. The amount of the inactive solvent used is not particularly limited as long as it is an amount that dissolves the reaction reagents, and can be appropriately selected from the range of 0.5L to 100L relative to 1 mol of the compound represented by the general formula (11). In addition, when the above-mentioned acid is used as a solvent, no solvent may be used.

[0077] The reaction temperature can be carried out in the boiling point region of the inactive solvent used from room temperature, and the reaction time varies according to the reaction scale and reaction temperature, and is not constant, and can be appropriately selected within the range of several minutes to 48 hours. After the reaction is completed, the target product can be separated by a conventional method from the reaction system containing the target product, and can be purified by recrystallization, column chromatography, etc. as needed to manufacture the target product. In addition, it can also be supplied to the next step without separation.

[0078] The compound represented by the general formula (14) can be produced from the compound represented by the general formula (12) by the step [e]. The reaction conditions of [e] are the same as those described above.

[0079] Manufacturing method of step [g] The compound represented by the general formula (2-1) can be produced by subjecting the compound represented by the general formula (14) to a cyclization reaction in the presence of a base and an inert solvent.

[0080] Examples of the base that can be used in the present reaction include hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide; alcoholates such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide; alkali metal hydrides such as sodium hydride and potassium hydride; carbonates such as lithium carbonate, lithium bicarbonate, sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, calcium carbonate, magnesium carbonate, and cesium carbonate; acetates such as lithium acetate, sodium acetate, and potassium acetate; and organic bases such as pyridine, picoline, lutidine, triethylamine, tributylamine, and N,N-diisopropylethylamine. The amount used can be appropriately selected within the usual range of 1 to 10 times the molar amount of the compound represented by the general formula (14).

[0081] As the inactive solvent that can be used in the present reaction, any solvent that does not significantly hinder the progress of the present reaction can be used, for example: chain or cyclic saturated hydrocarbons such as pentane, hexane, and cyclohexane; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; inactive solvents such as chain or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, and tetrahydrofuran; nitriles such as acetonitrile and propionitrile; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, and 1,3-dimethyl-2-imidazolidinone, etc. These inactive solvents can be used alone or in combination of two or more. The amount used can be appropriately selected within the range of 0.1 to 100 L per mol of the compound represented by the general formula (14).

[0082] The reaction temperature can be carried out in the boiling point region of the inactive solvent used from 0°C, and the reaction time varies according to the reaction scale, reaction temperature, etc., and is not constant, and can be appropriately selected within the range of several minutes to 48 hours. After the reaction is completed, the target product can be separated from the reaction system containing the target product by conventional methods, and the target product can be manufactured by purification by recrystallization, column chromatography, etc. as needed. In addition, it can also be supplied to the next step without separation.

[0083] Method for producing starting material 2 Among the compounds represented by the general formula (2) which are the starting materials of the compounds represented by the general formula (1-1) of the present invention, the compound (2-2) in which X is an oxygen atom can be produced by the following production method, i.e., by the following steps [h] and [i] based on the compound represented by the general formula (15). [Chemical formula 7]

[0084] {In the formula, R 1 Same as above. L represents a leaving group such as a halogen atom such as chlorine or bromine.

[0085] Manufacturing method of step [h] The compound represented by the general formula (17) can be produced by reacting the compound represented by the general formula (15) with the compound represented by the general formula (16) in the presence of a base and an inert solvent.

[0086] Examples of the base that can be used in the present reaction include hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide; alcoholates such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide; alkali metal hydrides such as sodium hydride and potassium hydride; carbonates such as lithium carbonate, lithium bicarbonate, sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, calcium carbonate, magnesium carbonate, and cesium carbonate; acetates such as lithium acetate, sodium acetate, and potassium acetate; organic bases such as pyridine, picoline, lutidine, triethylamine, tributylamine, and N,N-diisopropylethylamine, and the like. The amount used can be appropriately selected within the usual range of 1 to 10 times the molar amount of the compound represented by the general formula (15).

[0087] As the inactive solvent that can be used in the present reaction, any solvent that does not significantly inhibit the progress of the present reaction can be used, for example: linear or cyclic saturated hydrocarbons such as pentane, hexane, and cyclohexane; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; inactive solvents such as linear or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, and tetrahydrofuran; nitriles such as acetonitrile and propionitrile; esters such as methyl acetate; ketones such as acetone and methyl ethyl ketone; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, and 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, propanol, butanol, and 2-propanol, etc. These inactive solvents can be used alone or in combination of two or more. The amount used may be appropriately selected within the range of usually 0.1 to 100 L per 1 mol of the compound represented by the general formula (15).

[0088] This reaction is an equimolar reaction, so each compound can be used in an equimolar manner, or any compound can be used in excess. The reaction temperature in this reaction is usually carried out in the range of about 0°C to the boiling point of the solvent used, and the reaction time varies according to the reaction scale, reaction temperature, etc., and is not constant, and is usually appropriately selected within the range of a few minutes to 48 hours. After the reaction is completed, the target product can be separated from the reaction system containing the target product by conventional methods, and the target product can be manufactured by purification using recrystallization, column chromatography, etc. as needed. In addition, it can also be supplied to the next step without separation.

[0089] Manufacturing method of step [i] The compound represented by the general formula (2-2) can be produced by subjecting the compound represented by the general formula (17) to a cyclization reaction in the presence of an inert solvent.

[0090] As the inactive solvent that can be used in the present reaction, any solvent that does not significantly hinder the progress of the present reaction can be used, for example: chain or cyclic saturated hydrocarbons such as pentane, hexane, and cyclohexane; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; inactive solvents such as chain or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, and tetrahydrofuran; nitriles such as acetonitrile and propionitrile; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, and 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, propanol, butanol, and 2-propanol, etc. These inactive solvents can be used alone or in combination of two or more. The amount used can be appropriately selected within the range of 0.1 to 100 L per 1 mol of the compound represented by the general formula (17).

[0091] The reaction temperature in this reaction is usually carried out in the range of about room temperature to the boiling point of the solvent used, and the reaction time varies according to the reaction scale, reaction temperature, etc., and is not constant, and is usually appropriately selected within the range of a few minutes to 48 hours. After the reaction is completed, the target product can be separated from the reaction system containing the target product by a conventional method, and the target product can be manufactured by purification using recrystallization, column chromatography, etc. as needed. In addition, it can also be supplied to the next step without separation.

[0092] Method for producing starting material 3 In the compound represented by the general formula (3) as a starting material for the compound represented by the general formula (1-2) of the present invention, R 3 Compound (3-1) having a hydrogen atom can be produced by the following production method, that is, by the following steps [a] and [f] based on the compound represented by formula (18). The reaction conditions of [a] and [f] are the same as above. [Chemical formula 8]

[0093] {In the formula, R 2 and Y are the same as above.}

[0094] Method for producing starting materials 4 Among the compounds represented by the general formula (3) as the starting materials of the compounds represented by the general formula (1-2) of the present invention, the compound (3-2) in which Y is an oxygen atom can be produced by the following production method, i.e., by the following steps [j], [k], [l] and [f] based on the compound represented by the formula (18). It should be noted that the reaction conditions of [f] are the same as those described above. [Chemical formula 9]

[0095] {In the formula, R2 and R 3 Same as above. L represents a leaving group such as a halogen atom such as chlorine or bromine. R' and R" represent (C1-C6) alkyl such as methyl or ethyl.}

[0096] Manufacturing method of step [j] The compound represented by the general formula (21) can be produced by reacting the compound represented by the general formula (18) with the compound represented by the formula (19) in the presence of a base and an inactive solvent and in the presence or absence of a quaternary ammonium salt, and then reacting with the compound represented by the general formula (20).

[0097] Examples of the base that can be used in the present reaction include hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide; alcohol salts such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide; alkali metal hydrides such as sodium hydride and potassium hydride; carbonates such as lithium carbonate, lithium bicarbonate, sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, calcium carbonate, magnesium carbonate, and cesium carbonate; acetates such as lithium acetate, sodium acetate, and potassium acetate; organic bases such as pyridine, picoline, lutidine, triethylamine, tributylamine, and N,N-diisopropylethylamine, and the like. The amount used can be appropriately selected within the usual range of 1 to 10 times the molar amount of the compound represented by the general formula (18).

[0098] Examples of quaternary ammonium salts that can be used in the present reaction include tetrabutylammonium chloride, tetrabutylammonium bromide, tetrabutylammonium iodide, tetramethylammonium hydroxylate, tetraethylammonium hydroxylate, benzyltrimethylammonium hydroxylate, and the like. The amount used can be appropriately selected within the usual range of 0.001-fold to 1-fold mol relative to the compound represented by the general formula (18).

[0099] As the inactive solvent that can be used in the present reaction, any solvent that does not significantly inhibit the progress of the present reaction can be used, for example: linear or cyclic saturated hydrocarbons such as pentane, hexane, and cyclohexane; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; inactive solvents such as linear or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, and tetrahydrofuran; nitriles such as acetonitrile and propionitrile, and esters such as methyl acetate; ketones such as acetone and methyl ethyl ketone; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, and 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, propanol, butanol, and 2-propanol, etc. These inactive solvents can be used alone or in combination of two or more. The amount used may be appropriately selected within the range of usually 0.1 to 100 L per 1 mol of the compound represented by the general formula (18).

[0100] This reaction is an equimolar reaction, so each compound can be used in an equimolar manner, or any compound can be used in excess. The reaction temperature in this reaction is usually carried out in the range of about 0°C to the boiling point of the solvent used, and the reaction time varies according to the reaction scale, reaction temperature, etc., and is not constant, and is usually appropriately selected within the range of a few minutes to 48 hours. After the reaction is completed, the target product can be separated from the reaction system containing the target product by conventional methods, and the target product can be manufactured by purification using recrystallization, column chromatography, etc. as needed. In addition, it can also be supplied to the next step without separation.

[0101] Manufacturing method of step [k] The compound represented by the general formula (23) can be produced by reacting the compound represented by the general formula (21) with the compound represented by the general formula (22) in the presence or absence of an inert solvent.

[0102] As the inactive solvent that can be used in the present reaction, any solvent that does not significantly hinder the progress of the present reaction can be used, for example: linear or cyclic saturated hydrocarbons such as pentane, hexane, and cyclohexane; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; inactive solvents such as linear or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, and tetrahydrofuran; nitriles such as acetonitrile and propionitrile; esters such as methyl acetate; ketones such as acetone and methyl ethyl ketone; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, and 1,3-dimethyl-2-imidazolidinone, etc. These inactive solvents can be used alone or in combination of two or more, and the general formula (22) can also be used as a solvent. The amount used may be appropriately selected within the range of usually 0.1 to 100 L per 1 mol of the compound represented by the general formula (21).

[0103] This reaction is an equimolar reaction, so each compound can be used in an equimolar manner, or any compound can be used in excess. The reaction temperature in this reaction is usually carried out in the range of room temperature to the boiling point of the solvent used, and the reaction time varies according to the reaction scale, reaction temperature, etc., and is not constant, and is usually appropriately selected within the range of a few minutes to 48 hours. After the reaction is completed, the target product can be separated from the reaction system containing the target product by a conventional method, and the target product can be manufactured by purification with recrystallization, column chromatography, etc. as needed. In addition, it is also possible to supply the next step without separation.

[0104] Manufacturing method of step [1] The compound represented by the general formula (1-5) can be produced by reacting a compound represented by the general formula (23) with a compound represented by the general formula (24) in the presence of an inert solvent and in the presence or absence of a base.

[0105] Examples of the base that can be used in the present reaction include hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide; alcoholates such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide; alkali metal hydrides such as sodium hydride and potassium hydride; carbonates such as lithium carbonate, lithium bicarbonate, sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, calcium carbonate, magnesium carbonate, and cesium carbonate; acetates such as lithium acetate, sodium acetate, and potassium acetate; organic bases such as pyridine, picoline, lutidine, triethylamine, tributylamine, N,N-diisopropylethylamine, and diazabicycloundecene (DBU), and the like. The amount used can be appropriately selected within the usual range of 1 to 10 times the molar amount of the compound represented by the general formula (23).

[0106] As the inactive solvent that can be used in the present reaction, any solvent that does not significantly hinder the progress of the present reaction can be used, for example: chain or cyclic saturated hydrocarbons such as pentane, hexane, and cyclohexane; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; inactive solvents such as chain or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, and tetrahydrofuran; nitriles such as acetonitrile and propionitrile; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, and 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, propanol, butanol, and 2-propanol, etc. These inactive solvents can be used alone or in combination of two or more. The amount used can be appropriately selected within the range of 0.1 to 100 L per mol of the compound represented by the general formula (23).

[0107] This reaction is an equimolar reaction, so each compound can be used in an equimolar manner, or any compound can be used in excess. The reaction temperature in this reaction is usually carried out in the range of room temperature to the boiling point of the solvent used, and the reaction time varies according to the reaction scale, reaction temperature, etc., and is not constant, and is usually appropriately selected within the range of a few minutes to 48 hours. After the reaction is completed, the target product can be separated by a conventional method from the reaction system containing the target product, and the target product can be manufactured by purification using recrystallization, column chromatography, etc. as needed.

[0108] Below, Tables 1 to 4 illustrate representative examples of the compounds represented by the general formula (1) of the present invention, but the present invention is not limited thereto. In addition, Tables 5 and 6 illustrate specific examples of the compounds represented by the general formulas (2) and (3) that are starting materials for the compounds represented by the general formula (1) of the present invention. In the following tables, "Me" represents a methyl group, "Et" represents an ethyl group, "i-Pr" represents an isopropyl group, "c-Pr" represents a cyclopropyl group, "t-Bu" represents a tert-butyl group, "n-Hex" represents an n-hexyl group, "c-Hex" represents a cyclohexyl group, "Ph" represents a benzene ring, "Bn" represents a benzyl group, and "Ac" represents an acetyl group. Physical properties represent melting point (°C) or H 1 -NMR. H 1 -NMR data are shown in Table 7.

[0109] [Chemical formula 10]

[0110]

Table 1

[0111] [Table 2] Table 1 (Continued) (In Table 1, R 3 represents a hydrogen atom, X represents CH2, and Y represents an oxygen atom. ) Compound No. <![CDATA[R 1 ]]> <![CDATA[R 2 ]]> Physical properties 1-41 <![CDATA[CO2t-Bu]]> <![CDATA[3,4-Cl2-Ph]]> 163-165 1-42 <![CDATA[CO2t-Bu]]> 2-F-Ph 129-130 1-43 <![CDATA[CO2t-Bu]]> <![CDATA[2,6-F2-Ph]]> 152-153 1-44 <![CDATA[CO2t-Bu]]> <![CDATA[2,4-F2-Ph]]> 147-148 1-45 <![CDATA[CO2Bn]]> 4-F-Ph 117-118 1-46 4-OMe-Ph 4-F-Ph 164-165 1-47 4-CN-Ph 4-F-Ph 194-196 1-48 <![CDATA[4-CF3-Ph]]> 4-F-Ph 161-162 1-49 <![CDATA[4-CF3-Ph]]> <![CDATA[4-CF3-Ph]]> 192-193 1-50 <![CDATA[3-Cl-4-CF3-Ph]]> 4-F-Ph 159-162 1-51 5-F-pyridin-2-yl 4-F-Ph 193-195 1-52 5-CN-pyridin-2-yl 4-F-Ph 235-238 1-53 <![CDATA[5-CF3-pyridin-2-yl]]> 4-F-Ph 162-163 1-54 <![CDATA[3-Chloro-5-trifluoromethyl-pyridin-2-yl]]> 4-F-Ph 127-128 1-55 6-CN-pyridin-3-yl 4-F-Ph 190-192 1-56 <![CDATA[6-CF3-pyridin-3-yl]]> 4-F-Ph 248-249 1-57 5-I-pyrimidin-2-yl 4-F-Ph 203-204 1-58 5-F-pyrimidin-2-yl 4-F-Ph 192-194 1-59 5-CN-pyrimidin-2-yl 5-F-pyridin-2-yl 194-196 1-60 5-CN-pyrimidin-2-yl 4-F-Ph 256-258 1-61 5-CN-pyrimidin-2-yl <![CDATA[4-CF3-Ph]]> 193-195 1-62 <![CDATA[5-CF3-pyrimidin-2-yl]]> 4-F-Ph 210-211 1-63 <![CDATA[5-CF3-pyrimidin-2-yl]]> <![CDATA[4-CF3-Ph]]> 206-208 1-64 5-Br-pyrimidin-2-yl 4-OMe-Ph 148-150 1-65 5-Br-pyrimidin-2-yl 4-F-Ph 186-188 1-66 5-Br-pyrimidin-2-yl <![CDATA[4-CF3-Ph]]> 208-210 1-67 5-Br-4-Cl-pyrimidin-2-yl 4-F-Ph 144-146 1-68 <![CDATA[4-CF3-pyrimidin-2-yl]]> 4-F-Ph 189-190 1-69 <![CDATA[4,6-(OMe)2-pyrimidin-2-yl]]> 4-F-Ph 179-181 1-70 <![CDATA[4,5,6-Cl3-pyrimidin-2-yl]]> 4-F-Ph 189-191 1-71 5-Br-pyrazin-2-yl 4-F-Ph 243-245 1-72 6-Br-pyridazin-3-yl 4-F-Ph 216-217 1-73 3-Cl-pyridazin-6-yl 4-F-Ph 210-212 1-74 Benzoxazol-2-yl 4-F-Ph 202-204 1-75 Benzo[d]thiazol-2-yl 4-F-Ph NMR 1-76 <![CDATA[6-SCF3-benzothiazol-2-yl]]> 4-F-Ph 202-203 1-77 6-Cl-thiazolyl[4,5-b]pyridin-2-yl 4-F-Ph 218-219 1-78 6-Cl-quinoxalin-2-yl 4-F-Ph 214-216 1-79 6-Cl-Benzo[d]thiazol-2-yl 4-F-Ph 238-240 1-80 <![CDATA[6-CF3-benzothiazol-2-yl]]> 4-F-Ph 223-225

[0112]

Table 3

[0113]

Table 4

[0114]

Table 5

[0115]

Table 6

[0116]

Table 7

[0117] [Chemical formula 11]

[0118]

Table 8

[0119] [Chemical formula 12]

[0120]

Table 9

[0121] [Chemical formula 13]

[0122]

Table 10

[0123] [Chemical formula 14]

Table 11

[0125] [Chemical formula 15]

[0126]

Table 12

[0127]

Table 13

[0128]

Table 14

[0129]

Table 15

[0130] The pest control agent containing the compound represented by the general formula (1) of the present invention or its salt as an active ingredient can be used as an agricultural, forestry and horticultural pest control agent, an external parasite control agent for animals and an internal parasite control agent for animals. As an agricultural, forestry and horticultural pest control agent, it can be used to control various agricultural, forestry, horticultural, stored-grain pests, sanitary pests or nematodes that harm rice, fruit trees, vegetables, other crops and flowers. In addition, the agricultural and forestry horticultural insecticide containing the compound represented by the general formula (1) of the present invention or a salt thereof as an active ingredient is excellent in physical properties suitable for various labor-saving application methods, penetration and transfer activity, and environmental safety such as appropriate soil residue. In addition, the agricultural and forestry insecticide containing the compound represented by the general formula (1) of the present invention or its salt as an active ingredient has little effect on natural enemies, beneficial insects such as honey bees and bees, and environmental organisms such as chironomids.

[0131] Examples of the pests or nematodes include the following. Examples of the Lepidoptera pest include Parasa consocia, Anomis mesogona, Papilio xuthus, Matsumuraes azukivora, Ostrinia scapulalis, Spodoptera exempta, Hyphantria cunea, Ostrinia furnacalis, Pseudaletiaseparata, Tinea translucens, Bactra furfuryla, Parnara guttata, Marasmia exigua, Sesamia inferens, Brachmia triannulella, Monema sutchuenensis, and Parnara guttata. flavescens), Trichoplusia ni, Pleuroptya ruralis, Cystidia couaggaria, Lampides boeticus, Cephonodes hylas, Helicoverpa armigera, Phalerodonta manleyi, Eumeta japonica, Pieris brassicae, Malacosoma neustriatestacea, Stathmopoda masinissa, Cuphodes diospyrosella, Archips xylosteanus, Agrotis segetum, Tetramoera schistaceana, Papilio machaon hippocrates), Endoclytasinensis, Lyonetia prunifoliella, Phyllonorycterringoneella, Cydia kurokoi, Eucoenogenes aestuosa, Lobesiabotrana), Latoia sinica, Euzopherabatangensis, Phalonidia mesotypa, Spilosomaimparilis, Glyphodes pyloalis, Olethreutes mori, Tineola bisselliella, Endoclyta excrescens, Nemapogongranellus, Synanthedon hector, Cydia pomonella, Plutella xylostella, Cnaphalocrocis medinalis, Sesamiacalamistis, Scirpophaga incertulas), Pediasiateterrellus, Phthorimaea operculella, Stauropusfagi persimilis, Etiella zinckenella, Spodoptera exigua, Palpifer sexnotata, Spodoptera mauritia, Scirpophaga innotata, Xestia c-nigrum, Spodoptera depravata, Ephestia kuehniella, Angerona prunaria, Clostera anastomosis, Pseudoplusia includens, Matsumuraeses falcana, Helicoverpa assulta), Autographanigrisigna, Agrotis ipsilon, Euproctis pseudoconspersa, Adoxophyes orana, Caloptilia theivora, Homonamagnanima, Ephestiaelutella), Eumeta minuscula, Clostera anachoreta, Heliothis maritima, Sparganothis pilleriana, Busseola fusca, Euproctis subflava, Biston robustum, Heliothis zea, Aedialeucomelas, Narosoideus flavidorsalis, Viminia rumicis, Bucculatrix pyrivorella, Grapholita molesta, Spulerina astaurota, Ectomyelois pyrivorella, Chilosuppressalis, Acrolepiopsis sapporensis), Indian grain borer (Plodia interpunctella), cabbage borer (Hellula undalis), wheat moth (Sitotroga cerealella), Spodoptera litura, Eucosma aporema, strawberry long-winged moth (Acleriscomariana), Scopelodes contractus, Orgyia thyellina, Spodoptera frugiperda, Ostrinia zaguliaevi, Naranga aenescens, Andraca bipunctata, grape clearwing moth (Paranthreneregalis), Acosmeryx castanea, grape leafminer (Phyllocnistis toparcha), grape berry moth (Endopiza viteana), Eupocillia ambiguella), soybean armyworm (Anticarsia gemmatalis), tobacco moth (Cnephasia cinereipalpana), gypsy moth (Lymantriadispar), red pine caterpillar (Dendrolimusspectabilis), Leguminivora glycinivorella, Maruca testulalis, Matsumuraeses phaseoli, Caloptilia soyella, Phyllocnistis citrella, Omiodes indicate, Archips fuscocupreanus, Acanthoplusia agnata, Bambalina sp., Carposina niponensis, Conogethes punctiferalis, Synanthedon sp., Lyonetia clerkella, Papilio helenus, Colias erate poliographus, Phalera flavescens, Pieris spp. rapae crucivora), white cabbage butterfly (Pierisrapae), mulberry caterpillar (Euproctis similis), Suzuki false diamondback moth (Acrolepiopsissuzukiella), corn borer (Ostrinia nubilalis), cabbage armyworm (Mamestra brassicae), bridge worm (Ascotis selenaria), wormwood leaf roller (Phtheochroides clandestina), Kitakawa leaf roller (Hoshinoa adumbratana), round-spotted yellow leaf butterfly (Odonestis pruni japonensis), apple sword-shaped armyworm (Triaena intermedia), apple leaf roller (Adoxophyes orana fasciata), apple borer (Grapholita inopinata), white apple leaf roller (Spilonota ocellana), white bud leaf roller (Spilonotalechriaspis), pear star caterpillar (Illiberis pruni), apple silver moth (Argyresthia conjugella), Caloptilia zachrysa, Archips breviplicanus, Anomis flava, Pectinophoragossypiella), cotton leaf folder (Notarcha derogata), melon silk borer (Diaphania indica), tobacco budworm (Heliothis virescens), and golden-spotted borer (Eariascupreoviridis).

[0132] Examples of Hemiptera pests include Nezara antennata, Stenotus rubrovittatus, Graphosoma rubrolineatum, Trigonotylus coelestialium, Aeschynteles maculatus, Creontiades pallidifer, Dysdercus cingulatus, Chrysomphalus ficus, Aonidiella aurantii, Graptopsaltrianigrofuscata, Blissus leucopterus, Icerya purchasi, Piezodorus hybneri, Lagynotomus spp. elongatus), white-winged leafhopper (Thaia subrufa), black rice bug (Scotinophara lurida), rose aphid (Sitobion ibarae), rock bug (Stariodes iwasakii), coconut round shield scale (Aspidiotus destructor), white moss blind insect (Taylorilygus pallidulus), apricot tumor aphid (Myzus mumecola), Pseudaulacaspis prunicola, pea aphid (Acyrthosiphonpisum), striped whisker same edge bug (Anacanthocoris striicornis), sweet potato jumping blind bug (Ectometopterusmicantulus), Japanese two-star bug (Eysarcoris lewisi), brown mole stink bug (Molipteryx fuliginosa), large green leafhopper (Cicadella viridis), red-bellied constriction aphid (Rhopalosophum rufiabdominalis), Saissetia oleate, Trialeurodes vaporariorum, Aguriahanaquercus, Lygus spp., Euceraphis punctipennis, Andaspis kashicola, Coccus spp.pseudomagnoliarum), Cavelerius saccharivorus, Galeatus spinifrons, Macrosiphoniella sanborni, Aonidiella citrina, Halyomorpha mista, Stephanitis fasciicarina, Trioza camphorae, Leptocorisa chinensis, Trioza quercicola, Uhlerites latius, Erythroneura comes, Paromius exiguus, Duplaspidiotus claviger, Nephotettix sphenopsida nigropictus), Halticiellusinsularis, Perkinsiella saccharicida, Psyllamalivorella, Anomomeura mori, Pseudococcus longispinis, Pseudaulacaspis pentagona, Pulvinaria kuwacola, Apolyguslucorum, Togo hemipterus, Toxoptera aurantii, Saccharicoccus sacchari, Geoica lucifuga, Numata muiri, Comstockaspis perniciosa, Unaspis serrata, citri), Aulacorthumsolani, Eysarcoris ventralis, Bemisia argentifolii, Cicadellella spectra, Aspidiotus hederae, Liorhyssushyalinus, Calophya nigridorsalis, Sogatellafurcifera), Megoura crassicauda, ​​Brevicoryne brassicae, Aphis glycines, Leptocorisa oratorius, Nephotettix virescens, Uroeucon formosanum, Cyrtopeltis tennuis, Bemisia tabaci, Lecanium persicae, Parlatoria theae, Pseudaonidia paeoniae, Empoasca onukii, Plautiastali, Dysaphis tulipae, Macrosiphum euphorbiae, Stephanitis rubrum, and many other insect pests. pyrioides), Ceroplastes ceriferus, Parlatoria camelliae, Apolygus spinolai, Nephotettix cincticeps, Glaucias subpunctatus, Orthotylus flavosparsus, Rhopalosiphum maidis, Peregrinus maidis, Eysarcoris parvus, Cimex lectularius, Psyllaabieti, Nilaparvata lugens, Psylla tobirae, Eurydemarugosum, Schizaphis piricola, Psylla pyricola), Parlatoreopsis pyri, Stephanitis nashi, Dysmicoccuswistariae, Lepholeucaspis japonica, Sappaphis piri, Lipaphis erysimi, Neotoxopteraformosana), Rhopalosophum nymphaeae, Edwardsianarosae, Pinnaspisaspidistrae, Psylla alni, Speusotettix subfusculus, Alnetoidia alneti, Sogatella panicicola, Adelphocoris lineolatus, Dysdercus poecilus, Parlatoria ziziphi, Uhlerites debile, Laodelphax striatellus, Eurydemapulchrum, Cletus trigonus, Clovia punctata, Empoasca sp.), Coccus hesperidum, Pachybrachius luridus, Planococcus kraunhiae, Stenotus binotatus, Arboridia apicalis, Macrosteles fascifrons, Dolycoris baccarum, Adelphocoris triannulatus, Viteus vitifolii, Acanthocoris sordidus, Leptocorisa acuta, Macropes obnubilus, Cletus punctiger, Riptortus clavatus, Paratrioza cockerelli), Aphrophoracostalis, Lygus disponsi, Lygus saundersi, Crisicoccus pini, Empoasca abietis, Crisicoccusmatsumotoi, Aphis craccivora, Megacoptapunctatissimum), Eysarcoris guttiger, Lepidosaphes beckii, Diaphorina citri, Toxoptera citricidus, Planococcus citri, Dialeurodes citri, Aleurocanthus spiniferus, Pseudococcus citriculus, Zyginella citri, Pulvinaria citricola, Coccus discrepans, Pseudaonidia duplex, Pulvinaria aurantii, Lecanium corni, Nezara viridula, Stenodema calcaratum), Rhopalosiphum padi, Sitobionakebiae, Schizaphis graminum, Sorhoanus tritici, Brachycaudus helichrysi, Carpocoris purpureipennis, Myzuspersicae, Hyalopterus pruni, Aphis farinose yanagicola, Metasalis populi, Unaspis yanonensis, Mesohomotomacamphorae, Aphis spiraecola, Aphis pomi, Lepidosaphesulmi, Psylla mali), Heterocordylus flavipes, Myzusmalisuctus, Aphidonuguis mali, Orientus ishidai, Ovatus malicolens, Eriosoma lanigerum, Ceroplastesrubens, and Aphisgossypii) etc.

[0133] Examples of the Coleoptera pests include Xystroceraglobosa, Paederus fuscipes, Eucetonia roelofsi, Callosobruchus chinensis, Cylas formicarius, Hypera postica, Echinocnemus squameus, Oulema oryzae, Donacia provosti, Lissorhoptrus oryzophilus, Colasposoma dauricum, Euscepes postfasciatus, Epilaxna varivestis, Acanthoscelides obtectus, Diabrotica virgifera virgifera), Involvulus cupreus, Aulacophorafemoralis, Bruchus pisorum, Epilachna vigintioctomaculata, Carpophilus dimidiatus, Cassida nebulosa, Luperomorpha tunebrosa, Phyllotreta striolata, Psacotheahilaris, Aeolesthes chrysothrix, Curculio sikkimensis, Carpophilus hemipterus, Oxycetonia jucunda, Diabrotica spp.), Mimela splendens, Sitophilus zeamais, Tribolium castaneum, Sitophilus oryzae, Palorus subdepressus, Melolontha japonica, Anoplophora malasiaca, Neatus picipes, Leptinotarsa ​​decemlineata, Diabrotica undecimpunctata howardi, Sphenophorus venatus, Crioceris quatuordecimpunctata, Conotrachelus nenuphar, Ceuthorhynchidius albosuturalis, Phaedonbrassicae, Lasioderma serricorne), Sitona japonicus, Adoretus tenuimaculatus, Tenebrio molitor, Basileptabalyi, Hypera nigrirostris, Chaetocnema concinna, Anomala cuprea, Heptophylla picea, Epilachna vigintioctopunctata, Diabrotica longicornis, Eucetonia pilifera, Agriotes spp.), Attagenus unicolorjaponicus, Pagria signata, Anomala rufocuprea, Palorus ratzeburgii, Alphitobius laevigatus, Anthrenusverbasci, Lyctus brunneus, Tribolium confusum, Medythia nigrobilineata, Xylotrechus pyrrhoderus, Epitrix cucumeris, Tomicus piniperda, Monochamus alternatus, Popillia japonica, Epicauta gorhami, Sitophilus zeamais, Rhynchites heros), vegetable leaf weevil (Listroderescostirostris), four-striped bean weevil (Callosobruchus maculatus), apple frosted leaf weevil (Phyllobiusarmatus), slanted scarab beetle (Anthonomus pomorum), copper leaf beetle (Linaeidea aenea), and cotton boll weevil (Anthonomus grandis).

[0134] Examples of Dipteran pests include Culex pipienspallens, Pegomya hyoscyami, Liriomyza huidobrensis, Musca domestica, Chlorops oryzae, Hydrelliasasakii, Agromyza oryzae, Hydrellia griseola, Ophiomyia phaseoli, Dacus cucurbitae, Drosophila suzukii, Rhacochlaena japonica, Muscina stabulans, Megaselia spiracularis, and other flea flies, Clogmia albipunctata, Tipula oryzae, and the like. aino), Phormia regina, Culex tritaeniorhynchus, Anopheles sinensis, Hylemya brassicae, Asphondylia sp.), Delia platur a, Delia antiqua, Rhagoletis cerasi, Culex pipiens molestus forskal, Ceratitis capitata, Bradysia agrestis, Pegomya cunicularia, Liriomyza sativae, Liriomyza bryoniae, Chromatomyia horticola, Liriomyza chinensis, Culex quinquefasciatus, Aedes aegypti, Aedes albopictus, Liriomyza trifolii, Liriomyza sativae, Dacus dorsalis, Dacus citrus fruit fly tsuneonis), Sitodiplosis mosellana, Meromuza nigriventris, Anastrepha ludens, and Rhagoletis pomonella.

[0135] Examples of the Hymenoptera pests include Pristomyrmexpungens, scleroderma, Monomorium pharaohnis, Pheidole noda, Athalia rosae, Dryocosmus kuriphilus, Formica fuscajaponica, wasps, Athalia infumata infumata, Argepagana, Athalia japonica, Acromyrmex spp., Solenopsis spp., Arge mali, and Ochetellus glaber.

[0136] Examples of Orthoptera pests include Homorocoryphus lineosus, Gryllotalpa sp., Oxya hyla intricata, Oxya yeszoensis, Locusta migratoria, Oxya japonica, Homorocoryphus jezoensis, and Teleogryllus emma.

[0137] Examples of the Thysanoptera pests include Selenothrips rubrocinctus, Stenchaetothrips biformis, Haplothrips aculeatus, Ponticulothrips diospyrosi, Thrips flavus, Anaphothrips obscurus, Liothrips floridensis, Thrips simplex, Thrips nigropilosus, Heliothrips haemorrhoidalis, Pseudodendrothrips mori, Microcephalothrips abdominalis, Leeuwenia pasanii, Litotetothrips floridensis, Thrips simplex, Thrips nigropilosus, Heliothrips saemorrhoidalis, Pseudodendrothrips mori, Microcephalothrips abdominalis, Leeuwenia pasanii, and Litotetothrips serrata. pasaniae), Scirtothrips citri, Haplothrips chinensis, Mycterothrips glycines, Thripssetosus, Scirtothrips dorsalis, Dendrothrips minowai, Haplothrips niger, Thrips tabaci, Thrips alliorum, Thrips hawaiiensis, Haplothrips kurdjumovi, Chirothrips manicatus, Frankliniella intonsa, Thrips coloratus, Franklinella occidentalis, Thrips palmi, Frankliniella lilivora), and Liothrips vaneeckei, etc.

[0138] Examples of the Acarina pests include true ticks such as Leptotrombidium akamushi, Tetranychus ludeni, Dermacentor variabilis, Tetranychus truncatus, Ornithonyssus bacoti, Demodex canis, Tetranychus viennensis, Tetranychus kanzawai, and Rhipicephalus sanguineus, Cheyletus malaccensis, Tyrophagus putrescentiae, Dermatophagoides farinae, Latrodectus hasseltii, Dermacentor taiwanicus, Acaphylla theavagrans), Polyphagotarsonemus latus, Aculops lycopersici, Ornithonyssus sylvairum, Tetranychus urticae, Eriophyeschibaensis, Sarcoptes scabiei, Haemaphysalis longicornis, Ixodes scapularis, Tyrophagus similis, Cheyletuseruditus, Panonychus citri, Cheyletus moorei, Brevipalpus phoenicis, Octodectes cynotis, Dermatophagoides ptrenyssnus), Haemaphysalis flava, Ixodesovatus, Phyllocoptruta citri, Aculus schlechtendali, Panonychus schlechtendali,ulmi), Amblyomma americanum, Dermanyssus gallinae, Rhyzoglyphus robini, Sancassania sp., etc.

[0139] Examples of Isoptera pests include Reticulitermes miyatakei, Incisitermes minor, Coptotermes formosanus, Hodotermopsis japonica, Reticuliterme sp., Reticulitermes flaviceps amamianus, Glyptotermes kushimensis, Coptotermes guangzhoensis, Neotermes koshunensis, Glyptotermes kodamai, Glyptotermes satsumensis, Cryptotermes domesticus, Odontotermes formosanus, Glyptotermes nasutus, and Cryptotermes satsumensis. nakajimai), Nitobe crooked termite (Pericapritermes nitobei), and yellow-breasted termite (Reticulitermes speratus).

[0140] Examples of the Blattodea pests include Periplaneta fuliginosa, Blattella germanica, Blatta orientalis, Periplaneta brunnea, Blattella lituricollis, Periplaneta japonica, and Periplaneta americana.

[0141] Examples of the nematodes include Nothotylenchus acris, Aphelenchoides besseyi, Pratylenchus penetrans, Meloidogyne hapla, Meloidogyne incognita, Globodera rostochiensis, Meloidogyne javanica, Heterodera glycines, Pratylenchus coffeae, Pratylenchus neglectus, and Tylenchus semipenetrans.

[0142] Examples of the mollusks include the golden apple snail (Pomacea canaliculata), the giant African land snail (Achatina fulica), the two-lined slug (Meghimatium bilineatum), the Valencia land snail (Lehmanninavalentiana), the yellow slug (Limax flavus), and the Ryukyu ball snail (Acusta despecta sieboldiana).

[0143] The agricultural and horticultural pest control agent of the present invention also has a strong insecticidal effect on another pest, the tomato wheat moth (Tuta absoluta).

[0144] The agricultural and horticultural pest control agent containing the compound represented by the general formula (I) of the present invention or its salt as an active ingredient has a significant control effect on the pests that cause damage to paddy field crops, dry field crops, fruit trees, vegetables, other crops, flowers, etc. Therefore, according to the predicted period of pest generation, by treating the cultivation carriers such as seeds, paddy field water, stems and leaves or soil of seedling raising facilities, paddy fields, dry fields, fruit trees, vegetables, other crops, flowers, etc. before the generation of pests or at the time point of confirmed generation, the expected effect of the agricultural and horticultural pest control agent of the present invention can be exerted. Among them, the so-called osmotic transfer application based on the treatment of seedling raising soil of crops, flowers, etc., soil in planting holes during transplantation, plant roots, irrigation water, cultivation water in hydroponic cultivation, etc., and absorbing the compound of the present invention from the roots through the soil or without the soil is a preferred form of use.

[0145] The useful plants to which the agricultural and horticultural pest control agent of the present invention can be applied are not particularly limited, and examples thereof include: cereals (e.g., rice, barley, wheat, rye, oats, corn, etc.), legumes (soybeans, adzuki beans, broad beans, peas, kidney beans, peanuts, etc.), fruit trees / fruits (apples, citrus fruits, pears, grapes, peaches, plums, cherries, walnuts, chestnuts, almonds, bananas, etc.), leafy / fruit vegetables (cabbage, tomatoes, spinach, broccoli, lettuce, onions, onions (chives, shallots), green peppers, eggplants, strawberries, peppers, okra, leeks, etc.), root vegetables (carrots, potatoes, sweet potatoes, taro, radishes, turnips, lotus roots, etc.), The main crops are: lotus root, burdock, garlic, shallot, etc.), processing crops (cotton, hemp, beet, hop, sugar cane, beet, olive, rubber, coffee, tobacco, tea, etc.), melons (pumpkin, cucumber, watermelon, cantaloupe, melon, etc.), forage grass (wild grass, sorghum, timothy, clover, alfalfa, etc.), zoysia grass (Korean grass, bentgrass, etc.), ornamental crops such as spices (lavender, rosemary, thyme, parsley, pepper, ginger, etc.), flowers (chrysanthemum, rose, carnation, orchid, tulip, lily, etc.), garden trees (gingko, cherry, coral wood, etc.), forest trees (fir, silver fir, pine, cypress, fir, juniper, eucalyptus, etc.), etc.

[0146] The above-mentioned “plants” also include: plants that have been endowed with tolerance to HPPD inhibitors such as isoxaflutole, ALS inhibitors such as imazethapyr and thifensulfuron-methyl, EPSP synthase inhibitors such as glyphosate, glutamine synthetase inhibitors such as glufosinate, acetyl-CoA carboxylase inhibitors such as sethoxydim, and herbicides such as bromoxynil, dicamba, and 2,4-D through traditional breeding methods or genetic recombination technology.

[0147] As examples of "plants" that have been given tolerance through traditional breeding methods, there are rapeseed, wheat, sunflower, and rice that are tolerant to imidazolinone-based ALS-inhibiting herbicides such as imazethapyr, which are already being sold under the trade name of Clearfield (registered trademark). There are soybeans that are tolerant to sulfonylurea-based ALS-inhibiting herbicides such as thifensulfuron-methyl, which are also bred using traditional breeding methods, and are already being sold under the trade name of STS soybeans. As examples of plants that have been given tolerance to acetyl-CoA carboxylase inhibitors such as trion oxime-based and aryloxyphenoxypropionic acid-based herbicides, which are also bred using traditional breeding methods, there are SR corn and the like. In addition, plants endowed with tolerance to acetyl-CoA carboxylase inhibitors are described in Proc. Natl. Acad. Sci. USA, Vol. 87, pp. 7175-7179 (1990), etc. In addition, mutant acetyl-CoA carboxylases endowed with tolerance to acetyl-CoA carboxylase inhibitors are reported in Weed Science, Vol. 53, pp. 728-746 (2005), etc. By introducing such mutant acetyl-CoA carboxylase genes into plants using gene recombination technology, or introducing mutations associated with imparting resistance into plant acetyl-CoA carboxylases, plants endowed with tolerance to acetyl-CoA carboxylase inhibitors can be prepared. Furthermore, by using chimeraplasty technique (Gura T. 1999. Repairing the Genome's Spelling Mistakes. Science 285: 316-318.), by introducing base substitution mutations into nucleic acids into plant cells, and introducing site-specific amino acid substitution mutations into the acetyl-CoA carboxylase gene or ALS gene of the plant, etc., thereby producing plants that are tolerant to acetyl-CoA carboxylase inhibitors or ALS inhibitors, etc., and the agricultural and horticultural pest control agent of the present invention can also be used for these plants.

[0148] In addition, toxins expressed in genetically modified plants include: insecticidal proteins from Bacillus cereus or Bacillus popilliae; delta-endotoxins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bbl or Cry9C from Bacillus thuringiensis; insecticidal proteins such as VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins from nematodes; toxins produced by animals such as scorpion toxins, spider toxins, bee toxins or insect-specific neurotoxins; filamentous fungi toxins; toxins; lectins; agglutinins; protease inhibitors such as trypsin inhibitors, serine protease inhibitors, potato tuber specific protein (patatin), cysteine ​​protease inhibitors (cystatin), papain inhibitors; ribosome inactivating proteins (RIPs) such as ricin, corn-RIP, abrin, luffa seed ribosome inactivating protein (luffin), saporin, bryodin; steroid metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid UDP-glucosyl transferase, cholesterol oxidase; ecdysone inhibitors; HMG-CoA reductase; ion channel inhibitors such as sodium channel and calcium channel inhibitors; juvenile hormone esterase; diuretic hormone receptor; stilbene synthase; bibenzyl synthase; chitinase; glucanase, etc.

[0149] In addition, toxins expressed in such genetically modified plants also include: δ-endotoxin proteins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bbl, Cry9C, Cry34Ab or Cry35Ab; hybrid toxins of insecticidal proteins such as VIP1, VIP2, VIP3 or VIP3A; partially deleted toxins (truncated toxins), modified toxins (modified toxins). Hybrid toxins are made by new combinations of different domains of these proteins using recombinant technology. As a partially deleted toxin, Cry1Ab is known to have a part of the amino acid sequence deleted. As a modified toxin, one or more of the amino acids of the natural toxin are replaced. Examples of these toxins and recombinant plants that can synthesize these toxins are described in EP-A-0374753, WO 93 / 07278, WO 95 / 34656, EP-A-0427529, EP-A-451878, WO 03 / 052073 and the like.

[0150] The toxins contained in these recombinant plants impart resistance to beetle pests, hemipteran pests, dipteran pests, lepidopteran pests, and nematodes. The agricultural and horticultural pest control agent of the present invention can be used in combination with these technologies or in a systemized manner.

[0151] When used to control various pests, the agricultural and horticultural pest control agent of the present invention can be used directly, or appropriately diluted with water or the like, or in a suspended form, in an amount effective for controlling pests or nematodes for plants predicted to produce the pests and nematodes. For example, for pests and nematodes produced in fruit trees, cereals, vegetables, etc., in addition to spreading on stems and leaves, seeds can be treated by soaking seeds in the agent, seed coating, calcium peroxide (calper) treatment, soil full layer mixing, furrow application, bed soil incorporation, cell seedling treatment, planting hole treatment, plant foot treatment, top dressing, rice box treatment, submerged application, etc., to treat the soil, etc., so that it is absorbed from the roots and used. In addition, it can also be used in nutrient solution in nutrient solution (hydroponics) cultivation, fumigation or trunk injection, etc. In addition, the agricultural and horticultural pest control agent of the present invention can be used directly, or appropriately diluted with water, or in a suspended form, in an amount effective for pest control at a location where the pest is predicted to occur. For example, in addition to being spread on stored grain pests, household pests, sanitary pests, forest pests, etc., it can also be applied to building materials, used as fumigation, bait, etc.

[0152] As methods for seed treatment, for example, there can be listed: a method of diluting or undiluting a liquid or solid preparation and immersing the seeds in a liquid state to allow the agent to penetrate; a method of mixing a solid preparation or a liquid preparation with seeds, coating the preparation and causing it to adhere to the surface of the seeds; a method of mixing the preparation with an adhesive carrier such as a resin or a polymer and coating the seeds; a method of scattering the preparation near the seeds while planting, etc. The "seeds" subjected to the seed treatment refer to plants in the early stage of cultivation used for plant propagation, and examples thereof include, in addition to seeds, bulbs, tubers, seed potatoes, plant buds, bulbils, bulbs, or plants for vegetative propagation for cuttings. The "soil" or "cultivation carrier" of the plant when implementing the method of use of the present invention refers to a support for cultivating crops, and particularly refers to a support for rooting. The material thereof is not particularly limited as long as it is a material on which plants can grow, and may be so-called soil, seedling mats, water, etc. Specific materials include, for example, sand, pumice, vermiculite, diatomaceous earth, agar, gel-like substances, polymer substances, asbestos, glass wool, wood chips, bark, etc.

[0153] Examples of methods for spreading the pesticide on the stems and leaves of crops or on stored-grain pests, household pests, sanitary pests or forest pests include: a method of diluting a liquid preparation such as an emulsion or a flowable agent with water or a solid preparation such as a wettable powder or a wettable granule with water and spreading the preparation; a method of spreading a powder; or fumigation. As methods for application to the soil, for example, there can be listed: a method of diluting a liquid preparation in water or applying it to the roots of plants or a nursery bed for raising seedlings without diluting it; a method of spreading granules on the roots of plants or a nursery bed for raising seedlings; a method of spreading powders, wettable powders, wettable granules, granules, etc. before sowing or transplanting, and mixing them with the soil as a whole; a method of spreading powders, wettable powders, wettable granules, granules, etc. in planting pits, furrows, etc. before sowing or planting plants, etc.

[0154] As a method of application in a rice seedling raising box, the dosage form may differ depending on the application period, such as application at the time of sowing, application during the greening period, and application at the time of transplanting, but it can be applied in the form of powder, wettable granules, granules, etc. It can also be applied by mixing with soil, and soil can be mixed with powder, wettable granules or granules, such as bed soil mixing, covering soil mixing, and mixing into the entire soil. Soil and various formulations can be applied in layers alternately. As a method of applying to paddy fields, solid preparations such as large granules, pack agents, granules, wettable granules, and liquid preparations such as flowable agents and emulsions are usually spread in the paddy fields in the flooded state. In addition, when transplanting rice, appropriate preparations can be directly or mixed in fertilizers and then spread and injected into the soil. In addition, liquid medicines such as emulsions and flowable agents can be used in the source of water inflow into the paddy fields such as water outlets or irrigation devices, thereby saving effort in applying with the supply of water.

[0155] For dryland crops, from sowing to the seedling stage, the cultivation carrier close to the seed or plant body can be treated. For plants sown directly in dry fields, in addition to direct treatment of seeds, it is appropriate to treat the roots of the plants in cultivation. Granules can be used for spreading treatment, or the agent diluted or undiluted in water can be poured in liquid form. Sowing after mixing the granules with the cultivation carrier before sowing is also a preferred treatment. As a treatment for the sowing and seedling raising period of the cultivated plants to be transplanted, in addition to direct treatment of the seeds, it is preferred to pour a liquid agent into the seedling bed for raising the seedlings or to spread the granules. In addition, it is also a preferred treatment to treat the planting pit with the granules or to mix them with the cultivation carrier around the transplanting site during field planting. The agricultural and horticultural pest control agent of the present invention is usually prepared into a convenient form for use according to conventional methods for pesticide formulation. That is, the compound represented by the general formula (1) of the present invention or its salt can be used by dissolving, separating, suspending, mixing, impregnating, adsorbing or attaching it in a suitable inactive carrier or, if necessary, mixing it with an auxiliary agent in a suitable ratio to prepare a suitable dosage form (e.g., suspension, emulsion, liquid preparation, wettable powder, wettable granules, granules, powder, tablet, packaging agent, etc.).

[0156] In addition to the active ingredients, the agricultural and horticultural pest control agent of the present invention may also contain additives commonly used in pesticide preparations as needed. As the additives, there can be listed: carriers such as solid carriers and liquid carriers; surfactants, dispersants, wetting agents, binders, tackifiers, thickeners, colorants, extenders, spreaders, antifreeze agents, anti-caking agents, disintegrators, anti-decomposition agents, etc. In addition, preservatives, plant pieces, etc. may be used in the additives as needed. These additives may be used alone, or two or more may be used in combination.

[0157] As solid carriers, for example, natural minerals such as quartz, clay, kaolin, pyrophyllite, sericite, talc, bentonite, acid clay, palygorskite, zeolite, diatomaceous earth, etc., inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate, potassium chloride, etc., organic solid carriers such as synthetic silicic acid, synthetic silicates, starch, cellulose, plant powders (such as sawdust, coconut shells, corn cobs, tobacco stems, etc.), plastic carriers such as polyethylene, polypropylene, polyvinylidene chloride, urea, inorganic hollow bodies, plastic hollow bodies, fumed silica (fumed silica, white carbon black), etc. These solid carriers can be used alone or in combination of two or more.

[0158] Examples of the liquid carrier include: alcohols such as methanol, ethanol, propanol, isopropanol, butanol, etc., monohydric alcohols; polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, glycerol, etc.; polyol compounds such as propylene glycol ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, etc.; ethers such as ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether, tetrahydrofuran (THF), etc.; aliphatic hydrocarbons such as normal alkanes, cycloalkanes, isoalkanes, kerosene, mineral oil, etc. Hydrocarbons; aromatic hydrocarbons such as benzene, toluene, xylene, solvent naphtha, and alkylnaphthalene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; esters such as ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate, and dimethyl adipate; lactones such as γ-butyrolactone; amides such as dimethylformamide, diethylformamide, dimethylacetamide, and N-alkylpyrrolidone; nitriles such as acetonitrile; sulfur compounds such as dimethyl sulfoxide; vegetable oils such as soybean oil, rapeseed oil, cottonseed oil, and castor oil; water, etc. These liquid carriers may be used alone or in combination of two or more.

[0159] Examples of the surfactant used as a dispersant or wetting agent include: sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, sucrose fatty acid esters, polyoxyethylene fatty acid esters, polyoxyethylene resin acid esters, polyoxyethylene fatty acid diesters, polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, polyoxyethylene alkyl phenyl ethers, polyoxyethylene dialkyl phenyl ethers, polyoxyethylene alkyl phenyl ether formalin condensates, polyoxyethylene polyoxypropylene block copolymers, polystyrene polyoxyethylene block polymers, alkyl polyoxyethylene polypropylene block copolymer ethers, polyoxyethylene alkylamines, polyoxyethylene fatty acid amides, polyoxyethylene fatty acid bisphenyl ethers, polyalkylene benzyl phenyl ethers, polyoxyalkylene styryl phenyl ethers, acetylene glycols, polyoxyalkylene-added acetylene glycols, polyoxyethylene ether-type polysiloxanes, ester-type polysiloxanes, fluorine-based surfactants, polyoxyethylene castor oils, polyoxyethylene hydrogenated castor oils and other nonionic surfactants; alkyl Anionic surfactants such as sulfates, polyoxyethylene alkyl ether sulfates, polyoxyethylene alkylphenyl ether sulfates, polyoxyethylene styrylphenyl ether sulfates, alkylbenzene sulfonates, alkylaryl sulfonates, lignin sulfonates, alkyl sulfosuccinates, naphthalene sulfonates, alkylnaphthalene sulfonates, salts of formalin condensates of naphthalenesulfonic acid, salts of formalin condensates of alkylnaphthalenesulfonic acid, fatty acid salts, polycarboxylates, polyacrylic acid salts, N-methyl-fatty acid sarcosinates, resinates, polyoxyethylene alkyl ether phosphates, polyoxyethylene alkylphenyl ether phosphates; cationic surfactants such as alkylamine salts such as lauramine hydrochloride, stearylamine hydrochloride, oleylamine hydrochloride, stearylamine acetate, stearylaminopropylamine acetate, alkyltrimethylammonium chloride, alkyldimethylbenzalkonium chloride; amphoteric surfactants such as amino acid type or betaine type, etc. These surfactants may be used alone or in combination of two or more.

[0160] Examples of binders or thickeners include carboxymethyl cellulose or its salts, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinyl pyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, polyethylene glycol having an average molecular weight of 6,000 to 20,000, polyethylene oxide having an average molecular weight of 100,000 to 5,000,000, phospholipids (e.g., cephalin, lecithin, etc.), cellulose powder, dextrin, modified starch, polyaminocarboxylic acid chelate compounds, cross-linked polyvinyl pyrrolidone, copolymers of maleic acid and styrene, (meth)acrylic acid copolymers, half esters of polymers formed from polyols and dicarboxylic anhydride, water-soluble salts of polystyrene sulfonic acid, paraffin, terpene, polyamide resin, polyacrylate, polyoxyethylene, wax, polyvinyl alkyl ether, alkylphenol formalin condensate, synthetic resin emulsion, and the like.

[0161] Examples of the thickener include water-soluble polymers such as xanthan gum, guar gum, diutan gum, carboxymethyl cellulose, polyvinyl pyrrolidone, carboxyvinyl polymers, acrylic polymers, starch compounds, polysaccharides, high-purity bentonite, and inorganic fine powders such as fumed silica (white carbon black).

[0162] Examples of the colorant include inorganic pigments such as iron oxide, titanium oxide, and Prussian blue, and organic dyes such as alizarin dyes, azo dyes, and metal phthalocyanine dyes.

[0163] Examples of the antifreeze agent include polyols such as ethylene glycol, diethylene glycol, propylene glycol, and glycerol.

[0164] As auxiliary agents for preventing solidification or promoting disintegration, for example, polysaccharides such as starch, alginic acid, mannose, and galactose; polyvinyl pyrrolidone, fumed silica (fumed silica, white carbon black), ester gum, petroleum resin, sodium tripolyphosphate, sodium hexametaphosphate, metal stearate, cellulose powder, dextrin, copolymers of methacrylate, polyvinyl pyrrolidone, polyaminocarboxylic acid chelate compounds, sulfonated styrene-isobutylene-maleic anhydride copolymers, starch-polyacrylonitrile graft copolymers, etc.

[0165] Examples of the anti-decomposition agent include desiccants such as zeolite, quicklime, and magnesium oxide; antioxidants such as phenolic compounds, amine compounds, sulfur compounds, and phosphoric acid compounds; and ultraviolet absorbers such as salicylic acid compounds and benzophenone compounds.

[0166] Examples of the preservative include potassium sorbate and 1,2-benzothiazoline-3-one. Furthermore, other auxiliary agents such as functional spreading agents, activity enhancers such as metabolic decomposition inhibitors such as piperonyl butoxide, antifreeze agents such as propylene glycol, antioxidants such as BHT, and ultraviolet absorbers may be used as needed.

[0167] The blending ratio of the active ingredient compound can be increased or decreased as needed. In 100 parts by weight of the agricultural and horticultural pest control agent of the present invention, it can be appropriately selected and used from the range of 0.01 to 90 parts by weight. For example, when it is made into a dust, granules, emulsion or wettable powder, 0.01 to 50 parts by weight (0.01 to 50% by weight relative to the total weight of the agricultural and horticultural pest control agent) is suitable.

[0168] The dosage of the agricultural and horticultural pest control agent of the present invention varies depending on various factors, such as the purpose, target pests, development status of crops, pest production tendency, climate, environmental conditions, formulation, application method, application site, application period, etc., but can be appropriately selected from the range of 0.001 g to 10 kg, preferably 0.01 g to 1 kg per 10 ares based on the active ingredient compound according to the purpose. In order to expand the pests and diseases to be controlled, the applicable period of control, or to achieve a reduction in the amount of medicine, the agricultural and horticultural pest control agent of the present invention can also be mixed with other agricultural and horticultural insecticides, acaricides, nematicides, fungicides, biological pesticides, etc. In addition, depending on the usage scenario, it can also be mixed with herbicides, plant growth regulators, fertilizers, etc.

[0169] Examples of other agricultural and horticultural insecticides, acaricides, and nematicides used for this purpose include 3,5-xylyl methylcarbamate (XMC), fenobucarb (BPMC), Bt toxin insecticide compounds, CPCBS (chlorfenson), DCIP (dichlorodiisopropylether), DD (1,3-dichloropropene), DDT, NAC, O-4-dimethylsulfamoylphenyl O,O-diethylphosphorothioate (DSP), O-ethyl O-4-nitrophenyl phenylphosphorothioate (POP), and O-ethyl O-4-nitrophenyl phenylphosphorothioate (POP). phenylphosphonothioate (EPN), tripropylisocyanurate (TPIC), acrinathrin, azadirachtin, acynonapyr, azinphos-methyl, acequinocyl, acetamiprid, acetoprole, acephate, abamectin, afidopyropen, avermectin-B, amidoflumet, amitraz, alanycarb, aldicarb b), aldoxycarb, aldrin, alpha-endosulfan, alpha-cypermethrin, albendazole, allethrin, isazofos, isamidofos, isoamidofos, isoxathion, isocycloseram, isofenphos, isoprocarb (MIPC), epsilon-metofluthrin, epsilon-momfluorothrin, ivermectin,imicyafos, imidacloprid, imiprothrin, indazapyoxamet, indoxacarb, esfenvalerate, ethiofencarb, ethion, ethiprole, etoxazole, ethofenprox, ethoprophos, etrim fos), emamectin, emamectin-benzoate, endosulfan, empenthrin, oxazosulfyl, oxamyl, oxydemeton-methyl, oxydeprofos (ESP), oxibendazole, oxfendazole, potassium oleate, sodium oleate oleate), cadusafos, kappa-bifenthrin, cartap, carbaryl, carbosulfan, carbofuran, gamma-cyhalothrin, xylylcarb, quinalphos, kinoprene, chinomethionat, cloethocarb, clothianidin, clofentezine, chrysophanate, romafenozide), chlorantraniliprole, chlorethoxyfos, chlordimeform, chlordane, chlorpyrifos, chlorpyrifos-methyl, chlorphenapyr, chlorfenson, chlorfenvinphos, chlorfluazuron, chlorobenzilate, chlorobenzoate,Chloropralethrin, dicofol, salithion, cyhalodiamide, cyanophos (CYAP), diafenthiuron, diamidafos, cyantraniliprole, theta-cypermethrin, dienochlor, cyetpyrafen, cyenopyrafen, dioxathiophos abenzofos), diofenolan, sigma-cypermethrin, cyclaniliprole, dichlofenthion (ECP), cycloprothrin, dichlorvos (DDVP), dichloromezotiaz, disulfoton, dinotefuran, cyhalodiamide, cyhalothrin, cyph enothrin), cyfluthrin, diflubenzuron, cyflumetofen, diflovidazin, cyproflanilide, cyhexatin, cypermethrin, dimethylvinphos, dimethoate, dimpropyridaz, dimefluthrin, silafluofen, cyromazine ine), spidoxamat, spinetoram, spinosad, spirobudifen, spirodiclofen, spirotetramat, spiropidion, spiromesifen, sulfluramid, sulprofos, sulfoxaflor, zeta-cypermethrin, diazinon,Tau-fluvalinate, dazomet, thiacloprid, thiamethoxam, tioxazafen, thiodicarb, thiocyclam, thiosultap, thiosultap-sodium, thionazin, thiometon, tiorantraniliprole, DEET, dieldrin, tetrachlorvinphos trachlorantraniliprole), tyclopyrazoflor, tetrachlorvinphos, tetradifon, tetraniliprole, tetramethylfluthrin, tetramethrin, tebupirimfos, tebufenozide, tebufenpyrad, tefluthrin, teflubenzuron, demeton-S-methyl, temephos, deltamethrin, terbufos, doramectin, tralopyril, tralomethrin, transfluthrin, triazamate, triazuron, trichlamide, trichlorphon (DEP), trifluenfuronate, triflufenazine (triflumezopyrium), triflumuron, tolfenpyrad, naled: BRP, nicofluprole, nithiazine, nitenpyram, novaluron, noviflumuron, hydroprene, vaniliprole, vamidothion, parathion, parathion-methyl,halfenprox, halofenozide, bistrifluron, bisultap, hydramethylnon, hydroxy propyl starch, binapacryl, pyflubumide, bifenazate, bifenthrin, pymetrozine, pyraclorfos, pyrafluprole, pyridafenthion, pyridaben, pyridalyl, pyrifluquinazon, pyr iprole), pyriproxyfen, pirimicarb, pyrimidifen, pyriminostrobin, pirimiphos-methyl, pyrethrins, fipronil, fenazaquin, fenamiphos, bromopropylate, fenitrothion (MEP), fenoxycarb enoxycarb), fenothiocarb, phenothrin, fenobucarb, fensulfothion, fenthion (MPP), phenthoate (PAP), fenvalerate, fenpyroximate, fenpropathrin, fenbendazole, fenmezoditiaz, fosthiazate, formetanate, butathiofos, buprofezin, furathiocarb, prallethrin, fluacrypyrim, fluazaindolizine, fluazinam, fluazuron, fluensulfone, fluxametamide,fluchlordiniliprole, flucycloxuron, flucythrinate, fluvalinate, flupyradifurone, flufiprole, flupyradifurone, flupyroxystrobin, flupyrazofos, flupyrimin, flufenerim, flufenoxystrobin, Flufenoxuron, flufenzine, flufenoprox, fluproxyfen, flubrocythrinate, fluhexafon, flubendiamide, flupentiofenox, flumethrin, flurimfen, prothiofos, protrifenbute, flonicamid, propapho s), propargite (BPPS), profenofos, broflanilide, profluthrin, propoxur (PHC), flometoquin, alpha-bromadiolone, bromopropylate, beta-cyfluthrin, hexaflumuron, hexythiazox, heptafluthrin, heptylphosphine ( heptenophos), permethrin, benclothiaz, bendiocarb, benzpyrimoxan, bensultap, benzoximate, benfuracarb, phoxim, phosalone, fosthiazate, fosthietiaz, phosphamidon, phosphocarb, phosmet (PMP),Polynactins, formetanate, formothion, phorate, machine oil, malathion, milbemycin, milbemycin-A, milbemectin, mecarbam, mesulfenfos, methomyl, metaldehyde, metaflumizone, methamidophos, metam-ammonium, metam-sodium, methiocarb, methidathion (DMTP), methylisothiocyanate, methylneodecanamide, methylparathion on), metoxadiazone, methoxychlor, methoxyfenozide, metofluthrin, methoprene, metolcarb, meperfluthrin, mevinphos, monocrotophos, monosultap, momfluorothrin, lambda-cyhalothrin, ryanodine, lufenuron, rescalure, resmethrin, lepimectin, rotenone, levamisol hydrochloride), fenbutatin oxide, morantel tartarate, methyl bromide, tricyclohexyltin hydroxide (cyhexatin), calcium cyanamide, calcium polysulfide, sulfur, and nicotine-sulfate.

[0170] Examples of agricultural and horticultural fungicides used for the same purpose include aureofungin, azaconazole, azithiram, acypetacs, acibenzolar, acibenzolar-S-methyl, azoxystrobin, anilazine, amisulbrom, ampropylfos, ametoctradin, allyl alcohol, alcohol), 4-dodecyl-2,6-dimethylmorpholine (aldimorph), amobam, isotianil, isovaledione, isopyrazam, isofetamido, isofentamido, isofluxypram, isoprothiolane, ipconazole, ipfentrifluconazole, ipflufenoquin, iprodione, iprovalicarb, iprobenfos, imazalil, iminoctadine, metam, iminoctadine-albesilate, iminoctadine acetate hydrochloride iminoctadine-triacetate, imibenconazole, inpyrfluxam, uniconazole, uniconazole-P, echlomezole, edifenphos, etaconazole, ethaboxam, ethirimol, etem, ethoxyquin, etridiazole, enestroburin, enoxastrobin, epoxiconazole, oxadixyl, oxathiapiprolin, oxycarboxin, copper-8-quinolinolate,Oxytetracycline, 8-hydroxyquinoline copper (copper-oxinate), oxpoconazole, oxpoconazole-fumarate, oxolinic acid acid), octhilinone, ofurace, orysastrobin, sodium N-methyldithiocarbamate (carbam, metam-sodium), kasugamycin, carbamorph, carpropamid, carbendazim, carboxin, carvone, quinazamid, quinacetol, quinoxyfen, quinofumelin, chinomethionat, quinomethionat, captafol, captan, kiralaxyl, quinconazole, quintozene, guazatine, cufraneb, cuprobacterium am), coumoxystrobin, glyodin, griseofulvin, climbazole, cresol, kresoxim-methyl, chlozolinate, clotrimazole, chlobenthiazone, chloraniformethan, chloranil, chlorquinox, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, chloroneb, salicylanilide, zarilamid, cyazofamid, diethyl pyrocarbonate, diethofencarb, cyclafuramid,diclocymet, dichlozoline, diclobutrazol, cyclobutrifluram, dichlofluanid, cycloheximide, dichlobentiazox, diclomezine, dicloran, dichlorophen, dichlone, disulfiram, ditalimfos, dithiothrene ianon), diniconazole, diniconazole-M, zineb, dinocap, dinocton, dinosulfon, dinoterbon, dinobuton, dinopenton, dipymetitrone, dipyrithione, diphenylamine, difenoconazole, cyflufenamid, dimethoate diflumetorim, cyproconazole, cyprodinil, cyprofuram, cypendazole, simeconazole, dimethirimol, dimethomorph, cymoxanil, dimoxystrobin, ziram, silthiofam, streptomycin, spiroxamine, sultr open), sedaxane, zoxamide, dazomet, thiadiazin, tiadinil, thiadifluor, thiabendazole, tioxymid, thiochlorfenphim, thiophanate, thiophanate-methyl, thifluzamide, thicyofen, thioquinox,Thiram, decafentin, tecnazene, tecloftalam, tecoram, tetraconazole, debacarb, dehydroacetic acid, tebuconazole, tebufloquin, dodicin, dodine, dodecylbenzenesulphonic acid bisethylenediamine copper complex (II) copper[II]salt, DBEDC), dodemorph, drazoxolon, triadimenol, triadimefon, triazbutil, triazoxide, triamiphos, triarimol, trichlamide, triclopyricarb, tricyclazole, triticonazole, tridemorph, tributyltin oxide oxide), triflumizole, trifloxystrobin, triforine, tolylfluanid, tolclofos-methyl, tolprocarb, natamycin, nabam, nitrostyrene, nitrothal-isopropyl, nuarimol, copper nonylphenol sulfonate), halacrinate, validamycin, valifenalate, harpinprotein, picarbutrazox, bixafen, picoxystrobin, picobenzamide, pydiflumetofen, bithionol, bitertanol, hydroxyisoxazole,Hydroisoxazole-potassium, binapacryl, biphenyl, piperalin, hymexazol, pyraoxystrobin, pyracarbolid, pyraclostrobin, pyraziflumid, pyrazophos, pyrapropoyne, pyrametostrobin, pyriofenone , pyridinitril, pydiflumetofen, pyrisoxazole, pyridachlometyl, pyrifenox, pyribencarb, pyriminostrobin, pyrimethanil, pyroxychlor, pyroxyfur, pyroquilon, vinclozolin, ferbam, famox adone), fenapanil, fenamidone, fenaminosulf, fenaminstrobin, fenarimol, fenitropan, fenoxanil, ferimzone, ferbam, fentin, fenpiclonil, fenpicoxamid, fenpyrazamine, fenbuconazole, and furamide enfuram), fenpropidin, fenpropimorph, fenhexamid, phthalide, buthiobate, butylamine, bupirimate, fuberidazole, blasticidin-S, furametpyr, furaxyl, fluacrypyrim, fluazinam, fluindapyr,Fluoxastrobin, fluoxapiprolin, fluoxytioconazole, fluotrimazole, fluopicolide, fluopimomide, fluopyram, fluoroimide, furcarbanil, fluxapyroxad, fluquinconazole, furconazole, furconazole azole-cis), fludioxonil, flusilazole, flusulfamide, flutianil, flutolanil, flutriafol, flufenoxadiazam, flufenoxystrobin, furfural, flubeneteram, furmecyclox, flumetylsulforim, flumetover, flumorph flumorph, proquinazid, prochloraz, procymidone, prothiocarb, prothioconazole, pronitridine, propamocarb, propiconazole, propineb, furophanate, probenazole, bromuconazole, florylpicoxamid, Hexachlorobutadiene, hexaconazole, hexylthiofos, bethoxazin, benalaxyl, benalaxyl-M, benodanil, benomyl, pefurazoate, benquinox, penconazole, benzamorf, pencycuron, benzohydroxamic acid,Benzovindiflupyr, bentaluron, benthiazole, benthiavalicarb, benthiavalicarb-isopropyl, penthiopyrad, penflufen, boscalid, phosdiphen, fosetyl, fosetyl-Al, polyoxins, polyoxorim, polycarbamate, folpet, formaldehyde, machine oil oil), maneb, mancozeb, mandipropamid, mandestrobin, myclozolin, myclobutanil, mildiomycin, milneb, mecarbinzid, methasulfocarb, metazoxolon, metam, metam-sodium, metalaxyl, metalaxyl-M, metaylpicoxamid, metiram, methyl isothiocyanate isothiocyanate、mepthyldinocap、Metyltetraprole、metconazole、metsulfovax、methfuroxam、metominostrobin、metrafenone、mepanipyrim、mefenoxam、mefentrifluconazole、meptyldinocap、mepronil、mebenil、iodomethane、rabenzazole、methyl bromide、benzalkonium chloride、basic copper chloride、Basic copper sulfate, inorganic fungicides such as silver, sodium hypochlorote, cupric hydroxide, wettable sulfur, calcium polysulfide, potassium hydrogen carbonate, sodium hydrogen carbonate, inorganic sulfur, copper sulfate anhydride, nickel dimethyldithiocarbamate, copper compounds such as 8-hydroxyquinoline copper, zinc sulfate, and copper sulfate pentahydrate.

[0171] Similarly, examples of herbicides include 1-naphthylacetamide, 2,4-PA, 2,3,6-TBA, 2,4,5-T, 2,4,5-TB, 2,4-D, 2,4-DB, 2,4-DEB, 2,4-DEP, 3,4-DA, 3,4-DB, 3,4-DP, 4-CPA, 4-CPB, 4-CPP, MCP, MCPA, 2-methyl-4-chlorothioethyl (MCPA-thioethyl), MCPB, ioxynil, icafolin, and icafolin-methyl ester. hyl), aclonifen, azafenidin, acifluorfen, aziprotryne, azimsulfuron, asulam, acetochlor, atrazine, atraton, anisuron, anilofos, aviglycine, abscisic acid acid), amicarbazone, amidosulfuron, amitrole, aminocyclopyrachlor, aminopyralid, amibuzin, amiprophos-methyl, amethidione, ametryn, alachlor, allidochlor, alloxydim, alorac, iofensulfuron, isouron, isocarbam id), isoxachlortole, isoxapyrifop, isoxaflutole, isoxaben, isocil, isonoruron, isoproturon, isopropalin, isopolinate, isomethiozin, inabenfide, ipazine, iptriazopyrid, ipfencarbazone, iprymidam, imazaquin,Imazapic, imazapyr, imazamethapyr, imazamethabenz, imazamethabenz-methyl, imazamox, imazethapyr, imazosulfuron, indaziflam, indanofan, indolauxipyr, indolauxipyr-cyanomethyl, indolebutyric acid acid, uniconazole-P, eglinazine, esprocarb, ethametsulfuron, ethametsulfuron-methyl, ethalfluralin, ethiolate, ethychlozate ethyl), ethimuron, etinofen, ethephon, ethoxysulfuron, ethoxyfen, etnipromid, ethofumesate, etobenzanid, epyrifenacil, epronaz, erbon, endothal, oxadiazon, oxadiargyl, oxaziclomefone, oxasulfuron, oxapyrazone zon), oxyfluorfen, oryzalin, orthosulfamuron, orbencarb, cafenstrole, cambendichlor, carbasulam, carfentrazone, carfentrazone-ethyl, karbutilate, carbetamide, carboxazole, quizalofop, quizalofop-P, quizalofop-ethyl,xylachlor, quinoclamine, quinonamid, quinclorac, quinmerac, cumyluron, clacyfos, cliodinate, glyphosate, glufosinate, glufosinate-P, credazine, clethodim, cloxyfonac, clodinafop , clodinafop-propargyl, chlorotoluron, clopyralid, cloproxydim, cloprop, chlorbromuron, clofop, clomazone, chlomethoxynil, chlomethoxyfen, clomeprop, chlorazifop, chlorazine, chloranoprop cryl), chloramben, cloransulam, cloransulam-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorsulfuron, chlorthal, chlorthiamid, chlortoluron, chlornitrofen, chlorfenac, chlor fenprop), chlorbufam, chlorphthalim, chlorflurazole, chlorflurenol, chlorprocarb, chlorpropham, chlormequat, chloreturon, chloroxynil, chloroxuron, chlorotoluron, chloropon, saflufenacil,Cyanazine, cyanatryn, di-allate, diuron, diethamquat, dioxopyritrione, dicamba, cycluron, cycloate, cycloxydim, diclosulam, cyclosulfamuron, cyclopyranil, cyclopyrimorate, dichlorprop chlorprop), dichlorprop-P, dichlobenil, diclofop, diclofop-methyl, dichlormate, dichloralurea, diquat, cisanilide, disul, siduron, dithiopyr, diinitramine, cinidon-ethyl, dinosam, cinidon-ethyl osulfuron), dinoseb, dinoterb, dinofenate, dinoprop, cyhalofop-butyl, cypyrafluone, diphenamid, difenoxuron, difenopenten, difenzoquat, cybutryne, cyprazine, cyprazole, diflufenican, fluazifop-butyl diflufenzopyr, dipropetryn, cypromid, cyperquat, gibberellin, simazine, dimexano, dimesulfazet, dimethachlor, dimidazon, dimethametryn, dimethenamid, simetryn, simeton, dimepiperate,dimefuron, cinmethylin, swep, sulglycapin, sulcotrione, sulfallate, sulfentrazone, sulfosulfuron, sulfometuron, sulfometuron-methyl, secbumeton, sethoxydim, sebuthylazine, terbacil, methoxysulfuron daimuron), dazomet, dalapon, thiazafluron, thiazopyr, tiafenacil, thiencarbazone, thiencarbazone-methyl, tiocarbazil, tioclorim, thiobencarb, thidiazimin, thidiazuron, thifensulfuron, thiophenesulfon Thifensulfuron-methyl, desmedipham, desmetryn, tetflupyrolimet, tetrafluron, thenylchlor, tebutam, tebuthiuron, terbumeton, tepraloxydim, tefuryltrione, tembotrione, delachlor, terbacil , terbucarb, terbuchlor, terbuthylazine, terbutryn, topramezone, tralkoxydim, triaziflam, triasulfuron, triafamone, tri-allate, trietazine, tricamba, triclopyr, tridiphane, tritac,tritosulfuron, tripyrasulfone, trifludimoxazin, triflusulfuron, triflusulfuron-methyl, trifluralin, trifloxysulfuron, tripropindan, tribenuron, tribenuron-methyl, trifop, trifopsime, trimethyl trimeturon, tolpyralate, naptalam, naproanilide, naproxenamide, nicosulfuron, nitralin, nitrofen, nitrofluorfen, nipyraclofen, neburon, norflurazon, noruron, barban, paclobutrazol, paraquat raquat), parafluron, haloxydine, halauxifen, haloxyfop, haloxyfop-P, haloxyfop-methyl, halosafen, halosulfuron, halosulfuron-methyl, bilanfos, bixlozone, picloram, picolinafen, haloxyfop-P, haloxyfop-methyl, halosafen, halosulfuron, halosulfuron-methyl, bilanfos, bixlozone, picloram, picolinafen, bicyclopyrone, bispyribac, bispyribac-sodium, pydanon, pinoxaden, bipyrazone, bifenox, piperophos, hymexazol, pyraquinate, pyraclonil, pyrasulfotole, pyrazoxyfen, pyrazosulfuron,Pyrazosulfuron-ethyl, pyrazolate, bialafos, pyraflufen, pyraflufen-ethyl, pyriclor, 6-chloro-3-phenyl-4-pyridazinol (pyridafol), pyrithiobac, pyrithiobac-sodium, pyridate, pyriftalid, pyributicarb, pyriflubenzoate xim), pyribenzoxim, pyrimisulfan, primisulfuron, pyriminobac-methyl, pyroxasulfone, pyroxsulam, fenasulam, phenisopham, fenuron, fenoxasulfone, fenoxaprop, fenoxaprop-P, fenoxap rop-ethyl), phenothiol, fenoprop, phenobenzuron, fenquinotrione, fenthiaprop, fenteracol, fentrazamide, fenpyrazone, phenmedipham, phenmedipham-ethyl, butachlor, butafenacil ... mifos), buthiuron, buthidazole, butylate, buturon, butenachlor, butroxydim, butralin, butroxydim, flazasulfuron, flamprop, furyloxyfen, prynachlor, primisulfuron-methyl, fluazifop,Fluazifop-P, fluazifop-butyl, fluazolate, fluroxypyr, fluothiuron, fluometuron, fluoroglycofen, flurochloridone, fluorodifen, fluoronitrofen, fluoromidine, flucarbazone, flucarbazone sodium zone-sodium), fluchloraminopyr, fluchloraminopyr-tefuryl, fluchloralin, flucetosulfuron, fluthiacet, fluthiacet-methyl, flusulfinam, flupyrsulfuron, flufenacet, flufenican, flufenoximacil, flufenoximacil flufenpyr), flupropacil, flupropanate, flupoxam, flumioxazin, flumiclorac, flumiclorac-pentyl, flumipropyn, flumezin, fluometuron, flumetsulam, fluridone, flurtamone, fluroxypyr, flumethoxazole retilachlor), proxan, proglinazine, broclozone, procyazine, prodiamine, prosulfalin, prosulfuron, prosulfocarb, propaquizafop, propachlor, propazine, propanil, propyzamide, propisochlor,prohydrojasmon, propyrisulfuron, propham, profluazol, profluralin, prohexadione-calcium, propoxycarbazone, propoxycarbazone-sodium, profoxydim, bromacil, brompyrazon, prometryn, prometon ), bromoxynil, bromofenoxim, bromobutide, bromobonil, florasulam, florpyrauxifen, hexachloroacetone, hexazinone, pethoxamid, benazolin, penoxsulam, pebulate, beflubutamid, S-beflub utamid-M), vernolate, perfluidone, bencarbazone, benquitrione, benzadox, benzipram, benzylaminopurine, benzthiazuron, benzfendizone, bensulide, bensulfuron-methyl, benzoylprop, benzobicyc lon), benzofenap, benzofluor, bentazone, pentanochlor, benthiocarb, pendimethalin, pentoxazone, benfluralin, benfuresate, fosamine, fomesafen, foramsulfuron, forchlorfenuron, maleic hydrazide,2-Methyl-4-chloro-propionic acid (mecoprop), mecoprop-P, menoterb, mesosulfuron, mesosulfuron-methyl, mesotrione, mesoprotryne, metazachlor, methazole, metazosulfuron, methabenzthiazuron, metamitron, metamifop, N-methyldithiocarbamate (metam), methalpropalin, methiuron, methiozo lin), methiobencarb, methyldymron, metoxuron, metosulam, metsulfuron, metsulfuron-methyl, metflurazon, metobromuron, metobenzuron, methometon, metolachlor, metribuzin, mepiquat-chloride, mefenacet, mefluidide, monalide, monisouron, monuron, monochloroacetic acid acid), monolinuron, molinate, morfamquat, iodosulfuron, iodosulfuron-methyl-sodium, iodobonil, iodomethane, lactofen, lancotrione, linuron, rimisoxafen, rimsulfuron, lenacil, rhodethanil, calcium peroxide, methylbromide, etc.

[0172] In addition, as biopesticides, for example, viral preparations such as nuclear polyhedrosis virus (NPV), granulosis virus (GV), cytoplasmic polyhedrosis virus (CPV), entomopoxi virus (EPV), microbial pesticides used as insecticides or nematicides such as Monacrosporium phymatophagum, Steinernema carpocapsae, Steinernema kushidai, Pasteuria penetrans, Trichoderma lignorum, Agrobacterium radiobactor, non-pathogenic Erwinia carotovora, Bacillus subtilis, etc. Subtilis, etc., or biopesticides used as herbicides such as Xanthomonas campestris can be used in combination to achieve the same effect.

[0173] In addition, as a biopesticide, for example, the following ingredients can be used in combination: Encarsia formosa, Aphidius colemani, Aphidoletes aphidimyza, Diglyphus isaea, Dacnus abisibirica, Phytoseiulus persimilis, Amblyseius cucumeris, Orius sauteri) and other natural enemies, microbial pesticides such as Beauveria bassiana (Beauveria brongniartii), pheromones such as (Z)-10-tetradecene acetate, (E,Z)-4,10-tetradecadiene acetate, (Z)-8-dodecene acetate, (Z)-11-tetradecene acetate, (Z)-13-eicos-10-one, and 14-methyl-1-octadecene.

[0174] In addition, the compound represented by the general formula (1) of the present invention or its salt is also suitable for animal parasite control. Animal parasites live in or on the body of the host animal, causing harm to the host animal. They are roughly divided into external parasites that live on the body surface of the host animal and internal parasites that live in the body. The compound represented by the general formula (1) of the present invention or its salt can also be used as an external parasite control agent for animals or an internal parasite control agent for animals.

[0175] When the compound represented by the general formula (1) of the present invention or a salt thereof is used as an external parasite control agent for animals or an internal parasite control agent for animals, examples of animals that can be used include: livestock such as pigs, horses, cattle, sheep, goats, rabbits, camels, buffaloes, deer, minks, and chinchillas (Chinchilla lanigera); pets such as dogs, cats, birds, and monkeys; experimental animals such as rats, mice, golden hamsters, and guinea pigs; poultry such as chickens, wild ducks, ducks (a hybrid of wild ducks and domesticated ducks), quails, domesticated ducks, geese, and turkeys; humans, etc., but are not limited to these. In addition, it can also be applied to farmed fish such as sea bream, flounder, tuna, yellowtail (Hamachi), and eels, and crustaceans or shellfish such as shrimps, crabs, scallops, oysters, clams (Ruditapes philippinarum), and clams (Asiatic hard clams).

[0176] Examples of external parasites that can be controlled by the external parasite control agent for animals of the present invention include Rhipicephalus (Rhipicephalus (Boophilus) microplus, Rhipicephalus sanguineus, etc.), Amblyomma, Dermacentor, Haemaphysalis, Hyalomma, Ixodes, Rhipicentor, Margaropus, Argas, Otobius, Ornithodoros, Chorioptes (Chorioptes bovis, etc.), Psoroptes (Psoroptes spp.), and Psoroptes. ovis, etc.), Cheyletiella, Dermanyssus (Dermanyssus gallinae, etc.), Ortnithonyssus, Demodex (Demodex canis, etc.), Sarcoptes (Sarcoptes scabiei, etc.), Psorergates, Siphonaptera (Ctenocephalides felis, Ctenocephalides canis, etc.), Diptera (Musca spp., Gasterophilus intestinalis, Oestrus ovis, etc.), Phthiraptera (Bovicola ovis, Bovicola felis, Bovicola spp.), Bovis, etc.), Lepidoptera, Coleoptera, Homoptera, Haematopota, Tabanus, Haematobia (Haematobia irritans, etc.), Stomoxys, Lucilia, Lepeophtheirus, etc., but are not limited to these.

[0177] More specifically, examples of mites include Rhipicephalus microplus (Boophilus microplus), Rhipicephalus sanguineus, Haemaphysalis longicornis, hemaphysalis flava, Haemaphysalis campanulata, haemaphysalis concinna, haemaphysalis japonica, Haemaphysalis kitaokai, Haemaphysalis ias, Ixodes ovatus, Ixodes nipponensis, Ixodes persulcatus, Amblyomma testudinarium, Haemaphysalis megaspinosa, Dermacentor reticulatus, Dermacentor taiwanesis; Ornithonyssus mites such as Dermanyssus gallinae, Ornithonyssus sylviarum and Ornithonyssus bursa; Eutrombicula wichmanni, Leptotrombidium akamushi, Leptotrombidium pallidum, Leptotrombidium fuji, Leptotrombidium tosa, Neotrombicula autumnalis, Eutrombicula alfreddugesi, Helenicula miyagawai, and carnivorous mites such as Cheyletiella yasguri, Cheyletiella parasitivorax, and Cheyletiella blakei;Scabies mites such as Psoroptes cuniculi, Chorioptes bovis, Otodectes cynotis, Sarcoptes scabiei, Notoedres cati, and Demodex mites such as Demodex canis. ;

[0178] Examples of fleas include Pulicidae and Ceratephyllus. Examples of fleas belonging to the family Pulicidae include Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Echidnophagagallinacea, Xenopsylla cheopis, Leptopsylla segnis, Nosopsyllus fasciatus, and Monopsyllus anisus.

[0179] In addition, examples of external parasites that can be controlled by the external parasite control agent for animals of the present invention include lice such as Haematopinus eurysternus, Haematopinus asini, Dalmalinia ovis, Linognathus vituli, Haematopinus suis, Phthirus pubis, and Pediculus capitis, biting lice such as Trichodectes canis, and blood-sucking dipteran pests such as Tabanus trigonus, Culicoides schultzei, and Simulium ornatum.

[0180] Regarding the external parasite control agent for animals of the present invention, an appropriate solid carrier or liquid carrier is used according to the commonly used formulation, and it is mixed with adjuvants and the like in an appropriate proportion as needed to dissolve, suspend, mix, impregnate, adsorb or adhere, and is modulated into an appropriate dosage form (for example, liquid, emulsion, cream, ointment, suspension, aerosol) according to the purpose of use. The amount of the active ingredient in these preparations can be mixed in the range of 0.01 to 80.0 parts by mass in terms of the active ingredient in 100 parts by mass of the preparation. As the solid carrier or liquid carrier used, it is sufficient to use a carrier commonly used in animal medicines. Considering the ease of handling the target animal, it is preferred to use a liquid carrier. As a liquid carrier, for example, alcohols such as methanol, ethanol, isopropanol, tert-butyl alcohol, benzyl alcohol, propylene carbonate, N-methyl-2-pyrrolidone, water, etc. can be cited. Auxiliary agents may be used as needed. As the auxiliary agents, surfactants, antioxidants, emulsifiers, etc. may be used. For example, surfactants such as polyoxyethylene alkyl aryl ether, polyoxyethylene sorbitan monolaurate, alkyl allyl sorbitan monolaurate, alkyl benzene sulfonates, alkyl naphthalene sulfonic acid, lignin sulfonate higher alcohol sulfate, glycol monoalkyl ether, glycols, etc., emulsifiers such as sorbitan monooleate, sorbitan monolaurate, caprylic acid monoglyceride, capric acid monoglyceride, isostearic acid monoglyceride, propylene glycol monocaprylate, and antioxidants such as BHA and BHT may be mentioned.

[0181] The external parasite control agent for animals of the present invention can be administered to animals by a route having a desired effect such as topical, oral, parenteral and subcutaneous administration, without particular limitation, but topical administration is preferred. In topical administration, the agent can be administered by spot-on treatment of dripping a liquid agent onto the skin of the back of the shoulder blade of the target animal, pouring a liquid agent along the back of the target animal, spraying an aerosol agent of a liquid such as spray on or spray race, medicated bath (immersion), ear tags or collars loaded with agents, etc. For the dosage, the dosage can be appropriately selected from the range of about 0.1 to 500 mg for the active ingredient compound and about 0.01 to 20 ml for the control agent of the present invention per 1 kg of the body weight of the target animal.

[0182] In addition, other active ingredients may be used together as needed, for example, afoxolaner, fluralaner, lotilaner, sarolaner, albendazole, cambendazole, fenbendazole, flubendazole, mebendazole, oxfendazole, parbendazole, tiabendazole, triclabendazole. tricloban, amitraz, demiditraz, clorsulon, closantel, oxyclonazide, rafoxanide, cyphenothrin, flumethrin, permethrin, cyromazine, derquantel, diamphenethide, dicyclanil, dimethomorph dinotefuran), imidacloprid, nitenpyram, thiamethoxam, abamectin, doramectin, emamectin, eprinomectin, ivermectin, moxidectin, selamectin, milbemycinoxime, emodepside, epsiprantel, fipronil fipronil, fluazuron, fluhexafon, indoxacarb, levamisole, lufenuron, metaflumizone, methoprene, monepantel, morantel, niclosamide, nitroscanate, nitroxynil, novaluron, oxantel,Praziquantel, pyrantel, pyriprole, pyriproxyfen, sisapronil, spinosad, spinetoram, and triflumezopyrim. When used in combination, the preparation may be a mixture of two or more active ingredients before administration, or two or more different preparations may be administered separately.

[0183] Internal parasites that can be controlled by the internal parasite control agent for animals of the present invention are roughly divided into protozoa and helminths. Examples of protozoa that parasitize humans include Rhizopoda such as Entamoeba; Mastigophora such as Leishmania, Trypanosoma, and Trichomonas; Sporozoa such as Plasmodium and Toxoplasma; and Ciliophora such as Balantidium coli. Examples of helminths that parasitize humans include Ascaris lumbricoides, Anisakis, Toxocaracanis, Trichostrongylus, Enterobius vermicularis, hookworms (Ancylostoma duodenale, Necator americanus, Ancylostomabraziliense, etc.), Angiostrongylus, Gnathostoma, filariae (Filaria, Wuchereria bancrofti, Brugia malayi, etc.), Onchocerca, Dracunculus medinensis, Trichinella spiralis, Strongyloides stercoralis, etc.; Acannthocephala, such as Macracanthorhynchus hirudinaceus; Gordiacea, such as Gordiacea; Hirudinea, such as Hirudonipponia; Schistosoma japonicum japonicum), Schistosoma mansoni, Schistosoma haematobium, Clonorchis sinensis, Heterophyes heterophyes, Fasciola spp.), Paragonimus, etc.; Cestoda, etc., such as Diphyllobothrium latum, Sparganum mansoni, Sparganum proliferum, Diplogonoporus grandis, Taenia (Taenia saginata, Taenia solium, Echinococcus, etc.), Hymenolepis, Dipylidium caninum, Mesocestoides lineatus, Bertiella, Nybelinia surmenicola, etc., but not limited to these. .

[0184] Examples of protozoa that parasitize mammals or birds other than humans include Eimeria, Isospora, Toxoplasma, Neospora, Sarcocystis, Besnoitia, Hammondia, Cryptosporidium, and Caryospora in the Apicomplexa subphylum. Cocidia, Leucocytozoon, Plasmodium, Haemosporina, Theileria, Anaplasma, Eperythrozoon, Heamobartonella, Ehrlichia, Piroplasma, Hepatozoon, etc., and other Acrogastric species oon), Haemogregarina, Encephalitozoon and Nosema in Microspora, Trypanosoma and Leishmania in Mastigophora, Trypanosomatid, Chilomastix, Trichomonas, Mono cercomonas), Trichomonadida such as Histomonas, Diplomonadida such as Hexamita and Giardia, Rhizopoda such as Entamoeba histolytica (Entamoeba) in Sarcodina, Balantidium coli (Balantidium), Buxtonella, Entodinium in Ciliophora, etc.

[0185] Examples of helminths that parasitize mammals or birds other than humans include Ascaris, Toxocara cati (genus Toxocara), Toxascaris leonina (genus Toxascaris), Parascarisequorum (genus Parascaris), Ascaridia galli (genus Ascaridia), Heterakis gallinarum (genus Heterakis), Anisakis, etc., of the order Ascarida, Oxyuris equi (genus Oxyuris), Passalurus fossa (genus Passalurus), etc., among nematodes. ambiguus) (Passalurus), Oxyurida, Strongylus vulgaris (Strongylus), Haemonchus contortus (Haemonchus), Ostertagia ostertagi (Ostertagia), Trichostrongylus colubriformis (Trichostrongylus), Cooperia punctata (Cooperia), Nematodirus filicollis (Nematodirus), Hyostrongylus rubidus (Hystrongylus), Oesophagostomum radiatum (Oesophagostomum radiatum) (Oesophagostomum), Chabertia radiatum (Chabertia), Ancylostoma caninum (Ancylostoma), Uncinaria stenocephala (Uncinaria), Necator americanus (Necator), and Bovine hookworm (Bunostomumphlebotomum)(Bunostomum), Dictyocaulus viviparus)(Dictyocaulus), Metastrongylus elongatus)(Metastrongylus), Filaroides hirthi)(Filaroides), Aelurostrongylus abstrusus)(Aelurostrongulus), Angiostrongylus cantonensis)(Angiostrongylus), Syngamus trachea)(Syngamus), Stephanurus dentatus(Stephanurus), etc. Strongylida, Strongyloides stercoralis stercoralis)(Strongyloides), Micronema, Rhabditida, Thelazia rhodesi(Thelazia), Oxyspirura mansoni(Oxyspirura), Spirocerca lupi(Spirocerca), Gongylonema pulchrum(Gongylonema), Draschiamegastoma(Draschia), Habronema microstoma(Habronema), Ascarops strongylina(Ascarops), Physaloptera praeputialis (Physaloptera), Gnathostomaspinigerum (Gnathostoma), etc. Spirulina (Spirurida), Dirofilaria immitis (Dirofilaria), Setariaequina)((Setaria), Dipetalonema, Parafilariamultipapillosa)(Parafilaria), Onchocerca cervicalis(Onchocerca), etc. Filariida (Filariida), Parafilaria bovicola(Parafilaria), Stephanofilaria okinawaensis(Stephanofilaria), Trichuris vulpis(Trichuris), Capillaria bovis(Capillaria), Trichosomoidescrassicauda(Trichosomoides), Trichinella spiralis) (Trichinella), Dioctophyma renale (Dioctophyma), etc. Enoplida, etc.

[0186] Among the trematodes, Fasciolata such as Fasciola hepatica (genus Fasciola) and Fasciolopsis buski (genus Fasciolopsis) are listed, Paramphistomatidae such as Homalogaster paloniae (genus Homalogaster), Dicrocoelata such as Eurytrema pancreaticum (genus Eurytrema), Pharyngostomum (genus Pharyngostomum), Diplostomata such as Alaria, Echinostoma hortense)(Echinostoma), Echinochasmus and other Echinostomata, Paragonimus and other Troglotrematodea, Clonorchis salmincola and other Opisthorchiida, Heterophyes heterophyes and other Heterophyes, Metagonimus yokogawai and other Metagonimus, Prosthogonimus and other ovatus) (Prosthogonimus) and other Plagiorchida, Schistosoma japonicum (Schistosoma) and other Schistosoma, etc.Among the tapeworms, Diphyllobothrium nihonkaiense (genus Diphyllobothrium), Spirometra erinacei (genus Spirometra), Pseudophylidea, Anoplocephara perfoliata (genus Anoplocephara), Paranoplocephala mamillana (genus Paranoplocephala), Moniezia benedeni (genus Moniezia), Dipylidium caninum (genus Dipylidium), Mesocestoides lineatus (Mesocestoides), Taenia pisiformis, Taenia hydatigena (Tenia), Hydatigera taeniaeformis (Hydatigera), Multicepsmulticeps (Multiceps), Echinococcus granulosus (Echinococcus), Echinococcus multilocularis (Echinococcus), Taenia solium (Taenia), Taenia solium (Taenia), Taenia taeniaeformis (Taenia), saginata) (genus Taeniarhynchus), Hymenolepis diminuta (genus Hymenolepis), Hymenolepis nana (genus Vampirolepis), Raillietina tetragona (genus Raillietina), Amoebotaenia sphenoides (genus Amoebotaenia), etc. of the order Cyclophyllidea;Macracanthorhynchu shirudinaceus (Macracanthorhynchus), Moniliformismoniliformis (Moniliformis) and the like in the class Acanthocephala; Linguatula serrata (Linguatula) and the like in the class Ligulalepis; and various other parasites, but not limited to these. ;

[0187] In addition, as for helminths, for example, other names include: the order Enoplida belonging to the class Nematoda, such as Trichuris spp., Capillaria spp., Trichomosoides spp., Trichinella spp., etc., the order Rhabditia, such as Micronema spp., and Strongyloides spp., and the order Strongylida, such as Stronylus spp., Triodontophorus spp., Oesophagodontus spp., Trichomonas spp., Gyalocephalus spp. spp.), Cylindropharynx spp., Poteriostomum spp., Cyclococercus spp., Cylicostephanus spp., Oesophagostomum spp., Chabertia spp., Stephanurus spp., Ancylostoma spp., Uncinaria spp., Bunostomum spp., Globocephalus spp., Syngamus spp., Cyathostoma spp., Metastrongylus spp., Dictyocaulus spp.), Muellerius spp., Protostrongylus spp., Neostrongylus spp., Cystocaulus spp., Pneumostrongylus spp., Spicocaulus spp., Elaphostrongylus spp., Parelaphostrongylus spp., Crenosoma spp., Paracrenosoma spp.), Angiostrongylus spp., Aelurostrongylus spp., Filaroides spp., Parafilaroides spp., Trichostrongylus spp., Haemonchus spp., Ostertagia spp., Marshallagia spp., Cooperia spp., Nematodirus spp., Hyostrongylus spp., Obeliscoides spp., Amidostomum spp., and Ollulanus spp., etc.;

[0188] Examples of the order Oxyurida include Oxyuris spp., Enterobius spp., Passalurus spp., Syphacia spp., Aspiculuris spp., and Heterakis spp., and examples of the family Ascaridia include Ascaris spp., Toxascaris spp., Toxocara spp., Parascaris spp., Anisakis spp., and Cynomolgus spp. spp. and Ascaridis spp., as Spiruride, for example, Gnathosma spp., Physaloptera spp., Thelazia spp., Gongylonema spp., Habronema spp., Parabronema spp., Draschia spp. and Dracunculus spp., as Filariida, for example, Stephanofilaria spp., Parafilaria spp., Setaria spp., Loa spp., Dirofilaria spp. spp.), Litomosoides spp., Brugia spp., Wuchereria spp., Onchocerca spp., etc.

[0189] Examples of the class Acanthocephala include Filicollis spp., Moniliformis spp., Macracanthorhynchus spp., and Prosthenorchis spp.; examples of the class Monogenea of ​​Trematoda include Gyrodactylus spp., Dactylogyrus spp., and Polystoma spp.; examples of the class Diplostomum include Diplostomum spp., Posthodiplostomum spp., and spp.), Schistosoma spp., Trichobilharzia spp., Ornithbilharzia spp., Austrobilharzia spp., Gigantobilharzia spp., Leucochloridium spp., Brachylaima spp., Echinostoma spp., Echinoparyphium spp., Echinochasmus spp., Hypoderaeum spp., Fasciola spp., Fasciolides spp., Fasciolopsis spp., Cyclocoelum spp.), Typhlocoelum spp., Paramphistomum spp., Calicophoron spp., Cotylophoron spp., Gigantocotyle spp., Fischoederius spp., Gastrothylacus spp., Notocotylus spp., Catatropis spp., Plagiorchis spp., Prosthogonimus spp., Dicrocoelium spp., Eurytema spp.), Troglotrema spp., Paragonimus spp., Collyriclum spp., Nanophyetus spp., Opisthorchis spp., Clonorchis spp., Metorchis spp., Heterophyes spp., and Metagonimus spp., etc.;

[0190] As for the class of Taenia, examples of the order of Pseudophyllidea include Diphyllobothrium spp., Spirometra spp., Schistocephalus spp., Ligula spp., Bothridium spp., and Diplogonoporus spp., and examples of the order of Cyclophyllidea include Mesocestoides spp., Anoplocephala spp., Paranoplocehala spp., Moniezia spp., Thysanosomes spp.), Thysaniezia spp., Avitellina spp., Stilesia spp., Cittataenia spp., Andyra spp., Bertiella spp., Taenia spp., Echinococcus spp., Hydatigera spp., Davainea spp., Raillietina spp., Hymenolepis spp., Echinolepis spp., Echinocotyle spp., Diorchis spp. spp.), Dipylidium spp., Joyeuxiella spp., and Diplopylidium spp.; and other parasites belonging to the class Acanthocephala and the class Ligulalepis, but not limited to these.

[0191] The internal parasite control agent for animals of the present invention not only shows an effect on the control of parasites inhabiting intermediate hosts and final hosts, but also shows an effect on the control of parasites in the host organism. In addition, the compound represented by the general formula (I) of the present invention shows a control effect in the entire developmental stage of the parasite. For example, in protozoa, it is a cyst, a pre-cyst form, a trophozoite form or a split body, an amoeba, a gametocyte, a gamete, a fusion body, a sporozoite, etc. in the sexual reproduction period. In nematodes, it is an egg, a larva, and an adult. In addition, the compound to which the present invention relates can not only expel parasites in an organism, but also prevent parasitic infection by applying it in the environment of the infection route. For example, the following infections can be prevented before they occur: soil-borne infections from dry fields and park soil; percutaneous infections from water systems such as rivers, lakes, wetlands, and paddy fields; oral infections from feces of animals such as dogs and cats; oral infections from raw meat of marine fish, freshwater fish, crustaceans, shellfish, and livestock; infections from mosquitoes, horseflies, flies, cockroaches, mites, fleas, lice, assassin bugs, ticks, etc., etc.

[0192] The internal parasite control agent for animals of the present invention can be administered as a pharmaceutical for humans, mammals other than humans, or birds for the purpose of treating or preventing parasitic diseases. The method of administration can be any one of oral administration or parenteral administration. In the case of oral administration, it can be administered by being mixed into capsules, tablets, pills, powders, granules, microgranules, powders, syrups, enteric solvents, suspensions, pastes, or liquid beverages or feeds for animals. In the case of parenteral administration, it can be administered as an injection, a drop, a suppository, an emulsion, a suspension, a drop, an ointment, a cream, a liquid, a lotion, a spray, an aerosol, a cataplasm, a patch (tape), in a dosage form that can maintain mucosal or percutaneous absorption.

[0193] When the internal parasite control agent for animals of the present invention is used as a pharmaceutical for humans, mammals other than humans, or birds, the optimal amount of the active ingredient (effective amount) varies depending on the treatment or prevention, the type of parasite infection, the type and degree of infection, the dosage form, etc., and generally, in the case of oral administration, it is in the range of about 0.0001 mg / kg to 10000 mg / kg of body weight per day. In the case of parenteral administration, it is in the range of about 0.0001 mg / kg to 10000 mg / kg of body weight per day, either in a single dose or in divided doses.

[0194] The concentration of the active ingredient in the internal parasite control agent for animals of the present invention is generally about 0.001 to 100% by mass, preferably about 0.001 to 99%, and more preferably about 0.005 to 20% by mass. The internal parasite control agent for animals of the present invention may be a composition for direct administration or a high-concentration composition that is diluted to an appropriate concentration before use.

[0195] In addition, in order to enhance or supplement the effect of the internal parasite control agent for animals of the present invention, the above-mentioned other active ingredients may be used in combination as needed. When used in combination, it may be a preparation obtained by mixing two or more active ingredients before administration, or two or more different preparations may be administered separately. [Example]

[0196] Representative examples of the present invention are shown below, but the present invention is not limited to these examples.

[0197] Manufacturing Example 1 Preparation of tert-butyl 4-((4-fluorophenyl)carbamoyl)-5-hydroxy-3-oxo-3,6-dihydropyridine-1(2H)-carboxylate (Compound No. 1-36) [Chemical formula 16]

[0198] Sodium hydride (60% oil) (0.068 g, 1.7 mmol) was added to a super dehydrated N, N-dimethylformamide (6.0 mL) solution of tert-butyl 3,5-dioxopiperidine-1-carboxylate (0.30 g, 1.4 mmol) under ice-cooling, and stirred at room temperature for 30 minutes. 4-Fluorophenyl isocyanate (0.25 mL, 2.3 mmol) was added thereto under ice-cooling, and stirred at room temperature for 1 hour. After the reaction was completed, 10% hydrochloric acid, ethyl acetate and water were added for liquid separation, and the organic layer was washed with saturated brine. Anhydrous magnesium sulfate was added to the organic layer for drying, and after concentrating under reduced pressure, the residue was purified by silica gel column chromatography to obtain tert-butyl 4-((4-fluorophenyl)carbamoyl)-5-hydroxy-3-oxo-3,6-dihydropyridine-1(2H)-carboxylate (0.22 g, 0.063 mmol). Yield: 45% Physical properties: Melting point 135-136℃

[0199] Manufacturing Example 2 Preparation of tert-butyl 4-((4-chlorophenyl)carbamate)-5-hydroxy-3-oxo-3,6-dihydropyridine-1(2H)-carboxylate (Compound No. 2-13) [Chemical formula 17]

[0200] Add tert-butyl 3,5-dioxopiperidine-1-carboxylate (0.30 g, 1.4 mmol), cesium carbonate (0.68 g, 2.1 mmol), N,N-dimethylformamide (3.0 mL), stir for about 10 minutes, add 4-chlorophenylthioisocyanate (0.46 g, 2.7 mmol) under ice cooling, and stir at room temperature for 2 hours. After the reaction is completed, add 10% hydrochloric acid, separate with ethyl acetate / water, and dry the organic phase with anhydrous magnesium sulfate. After concentrating under reduced pressure, purify the residue by silica gel column chromatography to obtain tert-butyl 4-((4-chlorophenyl)carbamate)-5-hydroxy-3-oxo-3,6-dihydropyridine-1(2H)-carboxylate (0.44 g, 1.2 mmol). Yield: 86% Physical properties: Melting point 101-103℃

[0201] Manufacturing Example 3 Preparation of 2-(4-cyanophenyl)-N-(4-fluorophenyl)-4-hydroxy-6-oxo-3,6-dihydro-2H-1,2-oxazine-5-carboxamide (Compound No. 3-1) [Chemical formula 18]

[0202] 4-(4,6-dioxo-1,2-oxazahexyl-2-yl)benzonitrile (68 mg) was dissolved in dehydrated N,N-dimethylacetamide (2 mL), 4-fluorophenyl isocyanate (25 μL, 0.22 mmol), sodium hydride (60% oil) (11 mg, 0.22 mmol) were added, and then argon replacement was performed. After stirring at room temperature for 20 minutes, a saturated aqueous solution of ammonium chloride was added and extracted with ethyl acetate. After washing the organic phase with water and brine (brine), it was dried over anhydrous sodium sulfate and the solvent was removed by distillation under reduced pressure. The residue was purified by silica gel column chromatography to obtain 2-(4-cyanophenyl)-N-(4-fluorophenyl)-4-hydroxy-6-oxo-3,6-dihydro-2H-1,2-oxazine-5-carboxamide (39 mg, 0.11 mol). Yield: 58% Physical properties: Melting point 159-160℃

[0203] Manufacturing Example 4 Preparation of 1-(5-bromopyrimidin-2-yl)-N-(4-fluorophenyl)-5-hydroxy-3-oxo-1,2,3,6-tetrahydropyridine-4-carboxamide (Compound No. 1-65) [Chemical formula 19]

[0204] N-(4-fluorophenyl)-5-hydroxy-3-oxo-1,2,3,6-tetrahydropyridine-4-carboxamide hydrochloride (0.15 g, 0.52 mmol), potassium carbonate (0.36 g, 2.6 mmol), 5-bromo-2-chloropyrimidine (0.12 g, 0.62 mmol), and N,N-dimethylacetamide (5.0 mL) were added in sequence, and the mixture was stirred at 100°C for 3 hours. After the reaction was completed, 10% hydrochloric acid, ethyl acetate, and water were added for separation, and the organic layer was washed with saturated brine. Magnesium sulfate was added to dry the organic layer, and after concentrating under reduced pressure, the residue was purified by silica gel column chromatography to obtain 1-(5-bromopyrimidin-2-yl)-N-(4-fluorophenyl)-5-hydroxy-3-oxo-1,2,3,6-tetrahydropyridine-4-carboxamide (0.091 g, 0.22 mmol). Yield: 43% Physical properties: Melting point 186-188℃

[0205] Manufacturing Example 5 Preparation of tert-butyl 3-hydroxy-4-((4-(methylsulfonamido)phenyl)carbamoyl)-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate (Compound No. 1-208) [Chemical formula 20]

[0206] In 1-tert-butyl 4-ethyl 3-hydroxy-5-oxo-5,6-dihydropyridine-1,4(2H)-dicarboxylate (0.40 g, 1.4mmol), 20mL of toluene was added to N-(4-aminophenyl)methanesulfonamide (0.26g, 1.4mmol), and the mixture was refluxed and stirred for 2 hours. The reaction solution was concentrated under reduced pressure and the residue was recrystallized from ethyl acetate / methyl tert-butyl ether to obtain tert-butyl 3-hydroxy-4-((4-(methylsulfonamide)phenyl)carbamoyl)-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate (0.270g, 0.635mmol). Yield: 45% Physical properties: Melting point 221-222℃

[0207] Manufacturing Example 6 Preparation of 1-(Benzo[d][1,3]dioxole-5-carbonyl)-5-hydroxy-N-(4-(methylsulfonamide)phenyl)-3-oxo-1,2,3,6-tetrahydropyridine-4-carboxamide (Compound No. 1-217) [Chemical formula 21]

[0208] 5-Hydroxy-N-(4-(methylsulfonamide)phenyl)-3-oxo-1,2,3,6-tetrahydropyridine-4-carboxamide hydrochloride (90 mg, 0.25 mmol), benzo[d][1,3]dioxole-5-carboxylic acid (45 mg, 0.27 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (62 mg, 0.32 mmol), 4-dimethylaminopyridine (41 mg, 0.32 mmol), and triethylamine (127 mg, 1.24 mmol) were dissolved in 10 mL of chloroform and stirred at room temperature for 2 hours. The reaction solution was washed twice with 2 mol / L hydrochloric acid and once with a saturated aqueous ammonium chloride solution, and the organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The obtained residue was recrystallized from ethyl acetate / methyl tert-butyl ether to give 1-(benzo[d][1,3]dioxole-5-carbonyl)-5-hydroxy-N-(4-(methylsulfonamide)phenyl)-3-oxo-1,2,3,6-tetrahydropyridine-4-carboxamide (74 mg, 0.16 mmol). Yield: 63% Physical properties: Melting point 203-207℃

[0209] Reference Example 1 Preparation of 1-(1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)piperidine-3,5-dione (Compound No. 5-1) Reference Example 1-1 Production of tert-butyl (1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl) carbamate [Chemical formula 22]

[0210] After dissolving 1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-amine (2.9 g, 18 mmol) in pyridine (30 mL), di-tert-butyl dicarbonate (3.9 g, 18 mmol) was added under ice-cooling and stirred at room temperature for 3 hours. After the reaction was completed, 10% hydrochloric acid was added and extracted with ethyl acetate three times. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain tert-butyl (1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl) carbamate as a crude product. It was used in the next step without further purification.

[0211] Reference Example 1-2 Production of N-(tert-butoxycarbonyl)-N-(1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)glycine ethyl ester [Chemical formula 23]

[0212] The tert-butyl (1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl) carbamate and ethyl bromoacetate (1.5 mL, 13 mmol) obtained in the previous step were dissolved in N,N-dimethylacetamide (30 mL), and then sodium hydride (0.58 g, 14 mmol) was added under ice-cooling, and stirred at room temperature for 3 hours. After adding water to react, it was extracted with ethyl acetate 3 times. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain N-(tert-butoxycarbonyl)-N-(1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl) glycine ethyl ester (3.4 g, 9.7 mmol). Yield: 54% (2 steps) Physical properties: 1 H-NMR (CDCl3): δ7.04-6.61 (m, 1H), 4.54 (s, 2H), 4.21 (q, 2H), 3.84-3.83 (m, 3H), 1.54-1.47 (m, 9H), 1.32-1.24 (m, 3H)

[0213] Reference Examples 1-3 Production of (1-methyl-5-(trifluoromethyl-1H-pyrazol-3-yl)glycine ethyl ester [Chemical formula 24]

[0214] N-(tert-butoxycarbonyl)-N-(1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)glycine ethyl ester (3.4 g, 9.7 mmol) was dissolved in a 4M hydrogen chloride ethyl acetate solution (10 mL) and stirred at room temperature for 10 hours. After the reaction was completed, potassium carbonate and water were added, and the mixture was extracted three times with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain (1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)glycine ethyl ester (2.2 g, 8.8 mmol). Yield: 91% Physical properties: 1 H-NMR (CDCl3): δ5.91 (s, 1H), 4.22 (q, 2H), 3.94 (s, 2H), 3.78 (s, 3H), 1.26 (t, 3H)

[0215] Reference Examples 1-4 Preparation of N-(1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-N-(2-oxopropyl)glycine ethyl ester [Chemical formula 25]

[0216] Potassium carbonate (1.2 g, 8.4 mmol), chloroacetone (2.4 g, 25 mmol) and potassium iodide (4.2 g, 25 mmol) were added to a solution of (1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)glycine ethyl ester (2.1 g, 8.4 mmol) in N,N-dimethylacetamide (25 mL) in sequence, and the mixture was stirred at 100° C. for 3 hours under an argon atmosphere. After the reaction was completed, sodium thiosulfate, water and ethyl acetate were added for separation, and the organic layer was washed with 10% hydrochloric acid. Magnesium sulfate was added for drying, and the residue was purified by silica gel column chromatography after concentration under reduced pressure to obtain N-(1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-N-(2-oxopropyl)glycine ethyl ester (1.7 g, 5.4 mmol). Yield: 64% Physical properties: 1 H-NMR (CDCl3): δ5.80 (s, 1H), 4.19 (q, 2H), 4.13 (s, 2H), 4.05 (s, 2H), 3.75 (s, 3H), 2.19 (s, 3H), 1.27 (t, 3H)

[0217] Reference Examples 1-5 Preparation of 1-(1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)piperidine-3,5-dione (Compound No. 5-1) [Chemical formula 26]

[0218] Potassium tert-butoxide (0.73 g, 6.5 mmol) was added to a tetrahydrofuran (15 mL) solution of N-(1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-N-(2-oxopropyl)glycine ethyl ester (1.7 g, 5.4 mmol) and stirred at room temperature for 0.5 hours. After the reaction was completed, water and ethyl acetate were added to recover the aqueous phase. Then, 10% hydrochloric acid was added, and the organic phase was extracted with ethyl acetate, dried, and distilled to remove the solvent. The obtained residue was washed with ethyl acetate and tert-butyl methyl ether to obtain 1-(1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)piperidine-3,5-dione (0.16 g, 0.60 mmol). Yield: 11% Physical properties: Melting point 155-157℃

[0219] Reference Example 2 Preparation of 4-(4,6-dioxo-1,2-oxazepine-2-yl)benzonitrile (Compound No. 5-2) Reference Example 2-1 Production of 4-(((2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)methyl)(hydroxy)amino)benzonitrile [Chemical formula 27]

[0220] 4-(Hydroxyamino)benzonitrile (2.1 g, 16 mmol) was dissolved in dehydrated N,N-dimethylacetamide (78 mL), potassium carbonate (4.8 g, 34 mmol) and 6-(bromomethyl)-2,2-dimethyl-4H-1,3-dioxin-4-one (3.6 g, 16 mmol) were added, and the mixture was stirred at room temperature for 2 hours under an argon atmosphere. A saturated aqueous ammonium chloride solution was added at 0°C, and the mixture was extracted with ethyl acetate. The organic phase was washed with saturated brine, dried over sodium sulfate, and the solvent was removed by distillation under reduced pressure. The residue was purified by silica gel column chromatography to obtain 4-(((2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)methyl)(hydroxy)amino)benzonitrile (86 mg, 0.31 mmol). Yield: 2% Physical properties: 1 H-NMR (CDCl3): δ7.60-7.56 (m, 2H), 7.49 (s, 1H), 7.01-6.95 (m, 2H), 5.55 (s, 1H), 4.47 (d, 2H), 1.70 (s, 6H)

[0221] Reference Example 2-2 Preparation of 4-(4,6-dioxo-1,2-oxazepine-2-yl)benzonitrile (Compound No. 5-2) [Chemical formula 28] 4-(((2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)methyl)(hydroxy)amino)benzonitrile (52 mg, 0.19 mmol) was dissolved in toluene (3.8 mL) and heated under reflux for 1 hour under an argon atmosphere. The solvent was removed by distillation under reduced pressure to obtain 4-(4,6-dioxo-1,2-oxazepin-2-yl)benzonitrile (68 mg). Yield: quant. Physical properties: 1 H-NMR (CDCl3): δ7.91-7.87(m, 2H), 7.73-7.68(m, 2H), 4.58(s, 2H), 3.83(s, 2H)

[0223] Reference Example 3 Preparation of N-(4-fluorophenyl)-5-hydroxy-3-oxo-1,2,3,6-tetrahydropyridine-4-carboxamide hydrochloride (Compound No. 6-6) [Chemical formula 29]

[0224] To a solution of tert-butyl 4-((4-fluorophenyl)carbamoyl)-5-hydroxy-3-oxo-3,6-dihydropyridine-1(2H)-carboxylate (0.34 g, 0.97 mmol) in ethyl acetate (3.0 mL), a 4M hydrochloric acid solution in acetic acid (6.0 mL) was added and stirred at room temperature for 5 hours. After the reaction was completed, the mixture was concentrated under reduced pressure using a rotary evaporator, and the residue was washed with ethyl acetate and filtered to obtain N-(4-fluorophenyl)-5-hydroxy-3-oxo-1,2,3,6-tetrahydropyridine-4-carboxamide hydrochloride (0.28 g, 0.96 mmol). Yield: 99% Physical properties: Melting point 244-245℃

[0225] Reference Example 4 Preparation of 1-tert-butyl 4-ethyl 3-hydroxy-5-oxo-5,6-dihydropyridine-1,4(2H)-dicarboxylate Reference Example 4-1 Preparation of tert-butyl 4-(bis(methylthio)methylene)-3,5-dioxopiperidine-1-carboxylate [Chemical formula 30] In tert-butyl 3,5-dioxopiperidin-1-carboxylate (5.0g, 23mmol), cesium carbonate (30g, 94mmol), tetrabutylammonium bromide (8mg, 0.02mmol), add N,N-dimethylacetamide 100mL, stir at room temperature for 3 hours. Carbon disulfide (3.6g, 47mmol) was added dropwise and allowed to stand for 18 hours. Methyl iodide (7.3g, 52mmol) was added dropwise and stirred at room temperature for 5 hours. After adding 2mol / L hydrochloric acid to the reaction solution to make the pH less than 5, it was extracted with ethyl acetate. The organic layer was washed twice with 2mol / L hydrochloric acid and once with saturated ammonium chloride, and then the organic layer was dried with anhydrous sodium sulfate and then concentrated under reduced pressure to obtain tert-butyl 4-(bis(methylthio)methylene)-3,5-dioxopiperidin-1-carboxylate (5.5g, 17mmol). Yield: 77% Physical properties: Melting point 95-97℃

[0227] Reference Example 4-2 Preparation of 1-tert-butyl 4-ethyl 3-hydroxy-5-oxo-5,6-dihydropyridine-1,4(2H)-dicarboxylate [Chemical formula 31] 50 mL of ethanol was added to tert-butyl 4-(bis(methylthio)methylene)-3,5-dioxopiperidine-1-carboxylate (2.00 g, 6.30 mmol), and the mixture was stirred under reflux for 1 hour. The reaction solution was concentrated under reduced pressure to obtain 1-tert-butyl 4-ethyl 3-hydroxy-5-oxo-5,6-dihydropyridine-1,4(2H)-dicarboxylate (1.75 g, 6.14 mmol). Yield: 97% Physical properties: 1 H-NMR (CDCl3, 400MHz): δ14.5-16.1 (m, 1H), 4.40 (q, 2H) 3.9-4.1 (m, 4H), 1.47 (s, 9H), 1.40 (t, 3H)

[0229] The following are preparation examples, but the invention is not limited thereto. In the preparation examples, parts represent parts by weight.

[0230] Preparation Example 1. Mix and dissolve the above ingredients evenly to prepare an emulsion.

[0231] Preparation Example 2. 3 parts of the compound of the present invention Clay powder 82 parts 15 parts of diatomaceous earth powder Mix the above ingredients evenly and grind them into powder.

[0232] Preparation Example 3. 5 parts of the compound of the present invention 90 parts of mixed powder of bentonite and clay Calcium lignin sulfonate 5 parts Mix the above ingredients evenly, add appropriate amount of water to mix, granulate, and dry to make granules.

[0233] Preparation Example 4. 20 parts of the compound of the present invention Kaolin and synthetic highly dispersed silicate 75 parts 5 parts of a mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzene sulfonate Mix the above ingredients evenly and grind them into wettable powder.

[0234] Examples of biological tests are shown below, but the present invention is not limited to these.

[0235] Test Example 1. Insecticidal test against Plutella xylostella Adults of Plutella xylostella were released on cabbage seedlings to lay eggs. Two days after release, the cabbage seedlings with the eggs were immersed in a drug solution (the drug solution was obtained by diluting a drug containing the compound represented by the general formula (1) of the present invention as an active ingredient to 500 ppm) for about 30 seconds, air-dried, and then left to stand in a constant temperature room at 25°C. After immersion in the drug solution for 6 days, the number of surviving insects was investigated, and the corrected mortality rate was calculated by the following formula, and the judgment was made according to the following judgment criteria. 10 insects were placed in 1 area, and the results were repeated three times (triplicate).

[0236] [Mathematical formula 1]

[0237] Judgment criteria: A···Insect death rate 100% B···Insect death rate 99% to 90% C···Insect death rate 89% to 80% D···Insect death rate 79% to 50% E···Insect death rate 49% to 0%

[0238] As a result, the compounds represented by the general formula (1) of the present invention showed remarkable insecticidal activity, especially compound Nos. 1-5, 1-11, 1-12, 1-16, 1-18, 1-20, 1-22, 1-26, 1-28, 1-29, 1-31, 1-32, 1-33, 1-35, 1-36, 1-38, 1-39, 1-40, 1-44, 1-45, 1-48, 1-49, 1-51, 1-52, 1-53, 1-54, 1-55, 1-56, 1-57, 1-58, 1-59, 1-60, 1-61, 1-62, 1-63, 1-64, 1-65, 1-66, 1-67, 1-68, 1-69, 1-70, 1-71, 1-72, 1-73, 1-74, 1-75 The compounds of -53, 1-54, 1-56, 1-57, 1-59, 1-60, 1-61, 1-62, 1-63, 1-65, 1-68, 1-71, 1-72, 1-73, 1-74, 1-77, 1-79, 1-80, 1-85, 1-88, 1-89, 1-153, 1-160, 2-13, 2-31, 2-32, 2-36 and 3-1 showed excellent activity against Plutella xylostella as determined by A.

[0239] Test Example 2. Insecticidal test against Laodelphax striatellus The compound represented by the general formula (1) of the present invention or its salt is dispersed in water and diluted to a 500 ppm solution. Rice seedlings (variety: Nipponbare) are immersed in the solution for 30 seconds, air-dried and placed in a glass test tube. Ten heads of the third-instar gray planthopper are inoculated and then plugged with cotton plugs. The number of dead and alive insects is investigated 8 days after the inoculation. The corrected death rate is calculated by the following formula and judged according to the judgment criteria of Test Example 1.

[0240] [Mathematical formula 2]

[0241] As a result, among the compounds represented by the general formula (1) of the present invention, the compounds Nos. 1-20, 1-59, 1-62, 1-70, 1-195 and 2-31 showed excellent activity against Laodelphax striatellus in the A assessment.

[0242] Test Example 3. Insecticidal test against Frankliniella occidentalis Female adults of western flower thrips were inoculated on bean leaves and removed after 1 day of egg laying. Furthermore, after 3 days, the hatched larvae on the leaves were counted, and then a solution containing the compounds listed in Tables 1 to 3 as active ingredients diluted to 500 ppm was spread. The number of larvae of this species that survived 4 days after the treatment was investigated, and the corrected mortality rate was calculated by the following formula, and the judgment was made according to the judgment criteria of Test Example 1. Repeat 2 times (duplicate).

[0243] [Mathematical formula 3]

[0244] As a result, the compounds represented by the general formula (1) of the present invention showed significant insecticidal activity, and in particular, the compounds Nos. 1-36, 1-52, 1-53, 1-56, 1-57, 1-61, 1-62, 1-63, 1-65, 1-72, 1-88, 2-10, 2-31 and 2-38 showed excellent activity as determined by A against western flower thrips.

[0245] Test Example 4: Evaluation test on the effect on the movement of Dirofilaria immitis larvae 500 L-1 stage larvae of canine heartworms diluted in a predetermined adjustment solution were inoculated into each well of a 96-well plate, and a DMSO-diluted solution of the compound of the present invention was added to a final concentration of 50 ppm. Then, the activity was investigated after standing for 3 days. The activity inhibition rate of each treatment area was corrected and calculated based on the inhibition caused by the DMSO solution alone.

[0246] As a result, among the compounds represented by the general formula (1) of the present invention, the compounds Nos. 1-36, 1-50 and 1-89 showed a corrected movement inhibition rate of 50% or more.

[0247] Test Example 5. Evaluation test on the effect on the development of Dirofilaria immitis A predetermined adjustment solution, 8 to 20 L-3 stage larvae of dog heartworms, and a DMSO-diluted solution of the compound of the present invention were added to each well of a 24-well plate to a final concentration of 10 μM. After 7 days, the larvae that developed to the L-4 stage were counted, and the development inhibition rate from L3 stage larvae to L4-stage larvae was calculated.

[0248] As a result, among the compounds represented by the general formula (1) of the present invention, compounds Nos. 1-1, 1-6, 1-13, 1-23, 1-24, 1-25, 1-26, 1-27, 1-32, 1-47, 1-48, 1-52, 1-55, 1-56, 1-58, 1-71, 1-77, 1-80, 1-84, 1-154, 1-155, 1-156, 1-157 and 1-158 showed a development inhibition rate of more than 50%. Possibility of Industrial Application

[0249] The compound of the present invention and a salt thereof have excellent effects as a pest control agent.

Claims

1. A compound represented by the general formula (1) and its salts, In the formula, R 1 express (a1) (C1-C6) alkyl; (a2) (C2-C6) alkenyl; (a3) (C2-C6) alkynyl; (a4) (C3-C6) cycloalkyl; (a5) halo(C1-C6)alkyl; (a6) halo(C2-C6)alkenyl; (a7) halo(C2-C6)alkynyl; (a8) halo(C3-C6)cycloalkyl; (a9) a substituted (C1-C6)alkyl group having 1 to 3 substituents each independently selected from Substituent Group A; (a10) a substituted (C3-C6)cycloalkyl group having 1 to 3 substituents each independently selected from Substituent Group B; (a11) phenyl(C1-C6)alkyl, excluding phenylmethyl; (a12) a substituted phenyl (C1-C6) alkyl group having 1 to 5 substituents each independently selected from Substituent Group C on the ring; (a13) pyridyl(C1-C6)alkyl; (a14) a substituted pyridyl(C1-C6)alkyl group having 1 to 4 substituents independently selected from Substituent Group C on the ring; (a15) (C1-C6) alkylcarbonyl; (a16) halo(C1-C6)alkylcarbonyl; (a17) a substituted (C1-C6)alkylcarbonyl group having 1 to 3 substituents each independently selected from Substituent Group A; (a18) phenylcarbonyl; (a19) a substituted phenylcarbonyl group having 1 to 5 substituents each independently selected from Substituent Group C on the ring; (a20) pyridylcarbonyl; (a21) a substituted pyridylcarbonyl group having 1 to 4 substituents each independently selected from Substituent Group C on the ring; (a22) furanylcarbonyl; (a23) a substituted furanylcarbonyl group having 1 to 3 substituents each independently selected from Substituent Group C on the ring; (a24) thienylcarbonyl; (a25) a substituted thienylcarbonyl group having 1 to 3 substituents each independently selected from Substituent Group C on the ring; (a26) pyrazolylcarbonyl; (a27) a substituted pyrazolylcarbonyl group having 1 to 3 substituents each independently selected from Substituent Group C on the ring; (a28) triazolylcarbonyl; (a29) a substituted triazolylcarbonyl group having 1 to 2 substituents each independently selected from Substituent Group C on the ring; (a30) dioxodihydrodibenzofuranylcarbonyl; (a31) a substituted dioxodihydrodibenzofuranylcarbonyl group having 1 to 3 substituents each independently selected from Substituent Group C on its ring; (a32) dihydrobenzodioxinylcarbonyl; (a33) a substituted dihydrobenzodioxinylcarbonyl group having 1 to 7 substituents each independently selected from Substituent Group C on its ring; (a34) (C1-C6) alkoxycarbonyl; (a35) halo(C1-C6)alkoxycarbonyl; (a36) a substituted (C1-C6)alkoxycarbonyl group having 1 to 3 substituents each independently selected from Substituent Group A; (a37) phenyl(C1-C6)alkoxycarbonyl; (a38) a substituted phenyl(C1-C6)alkoxycarbonyl group having 1 to 5 substituents each independently selected from Substituent Group C; (a39) (C1-C6) alkylsulfonyl; (a40) (C3-C6) cycloalkylsulfonyl; (a41) halo(C1-C6)alkylsulfonyl; (a42) halo(C3-C6)cycloalkylsulfonyl; (a43) a substituted (C1-C6)alkylsulfonyl group having 1 to 3 substituents each independently selected from Substituent Group A; (a44) a substituted (C3-C6)cycloalkylsulfonyl group having 1 to 3 substituents each independently selected from Substituent Group B; (a45) halo(C1-C6)alkoxyhalo(C1-C6)alkylsulfonyl; (a46) phenylsulfonyl; (a47) a substituted phenylsulfonyl group having 1 to 5 substituents each independently selected from Substituent Group C; (a48) thienylsulfonyl; (a49) a substituted thienylsulfonyl group having 1 to 3 substituents each independently selected from Substituent Group C on the ring; (a50) pyrazolylsulfonyl; (a51) a substituted pyrazolylsulfonyl group having 1 to 3 substituents each independently selected from Substituent Group C on the ring; (a52) thiazolylsulfonyl; (a53) a substituted thiazolylsulfonyl group having 1 to 2 substituents each independently selected from Substituent Group C on the ring; (a54) isoxazolylsulfonyl; (a55) a substituted isoxazolylsulfonyl group having 1 to 2 substituents each independently selected from Substituent Group C on the ring; (a56) quinolylsulfonyl; (a57) a substituted quinolylsulfonyl group having 1 to 6 substituents each independently selected from Substituent Group C on the ring; (a58) phenyl(C1-C6)alkylsulfonyl; (a59) a substituted phenyl (C1-C6) alkylsulfonyl group having 1 to 5 substituents each independently selected from Substituent Group C; (a60) aryl; (a61) a substituted aryl group having one or more substituents each independently selected from the substituent group D on the ring; (a62) a 5- to 10-membered heterocyclic group; (a63) a substituted 5- to 10-membered heterocyclic group having at least one substituent each independently selected from the substituent group D on the ring; (a64) (C3-C6) cycloalkylcarbonyl; (a65) a substituted (C3-C6)cycloalkylcarbonyl group having 1 to 3 substituents each independently selected from Substituent Group B; (a66) isoxazolylcarbonyl; (a67) a substituted isoxazolylcarbonyl group having 1 to 2 substituents each independently selected from Substituent Group C on the ring; (a68) phenylaminocarbonyl; (a69) a substituted phenylaminocarbonyl group having 1 to 5 substituents each independently selected from Substituent Group C on the ring; (a70) pyrimidinylcarbonyl; (a71) a substituted pyrimidinylcarbonyl group having 1 to 3 substituents each independently selected from Substituent Group C on the ring; (a72) pyrazinylcarbonyl; (a73) a substituted pyrazinylcarbonyl group having 1 to 3 substituents each independently selected from Substituent Group C on the ring; (a74) pyridazinylcarbonyl; (a75) a substituted pyridazinylcarbonyl group having 1 to 3 substituents each independently selected from Substituent Group C on the ring; (a76) naphthylcarbonyl; (a77) a substituted naphthylcarbonyl group having 1 to 7 substituents each independently selected from Substituent Group C on the ring; (a78) quinolylcarbonyl; or (a79) a substituted quinolylcarbonyl group having 1 to 6 substituents each independently selected from Substituent Group C on the ring, R 2 express (b1) amino group; (b2) (C1-C6) alkyl; (b3) (C2-C6) alkenyl; (b4) (C2-C6) alkynyl; (b5) (C3-C6) cycloalkyl; (b6) halo(C1-C6)alkyl; (b7) halo(C2-C6)alkenyl; (b8) halo(C2-C6)alkynyl; (b9) halo(C3-C6)cycloalkyl; (b10) a substituted (C1-C6)alkyl group having 1 to 3 substituents each independently selected from Substituent Group A; (b11) a substituted (C3-C6) cycloalkyl group having 1 to 3 substituents independently selected from Substituent Group B on the ring; (b12) an N-(C1-C6) alkylamino group; (b13) N,N-di(C1-C6)alkylamino; (b14) N-(C1-C6)alkyl-N-phenylamino; (b15) (C1-C6) alkylsulfonyl; (b16) N-(C1-C6)alkylaminosulfonyl; (b17) N,N-di(C1-C6)alkylaminosulfonyl; (b18) piperidinyl; (b19) morpholinyl; (b20) phenyl; (b21) a substituted phenyl group having 1 to 5 substituents each independently selected from the substituent group E on the ring; (b22) pyridyl; (b23) a substituted pyridyl group having 1 to 4 substituents independently selected from the substituent group E on the ring; (b24) pyridazinyl; (b25) a substituted pyridazinyl group having 1 to 3 substituents each independently selected from Substituent Group E on the ring; (b26) pyrimidinyl; (b27) a substituted pyrimidinyl group having 1 to 3 substituents each independently selected from Substituent Group E on the ring; (b28) pyrazinyl; (b29) a substituted pyrazinyl group having 1 to 3 substituents each independently selected from Substituent Group E on the ring; (b30) triazine group; (b31) a substituted triazine group having 1 to 2 substituents each independently selected from the substituent group E on the ring; (b32) furanyl; (b33) a substituted furanyl group having 1 to 3 substituents each independently selected from Substituent Group E on the ring; (b34) oxazolyl; (b35) substituted oxazolyl having 1 to 2 substituents independently selected from Substituent Group E on the ring; (b36) isoxazolyl; (b37) a substituted isoxazolyl group having 1 to 2 substituents each independently selected from Substituent Group E on the ring; (b38) thienyl; (b39) a substituted thienyl group having 1 to 3 substituents each independently selected from Substituent Group E on the ring; (b40) thiazolyl; (b41) a substituted thiazolyl group having 1 to 2 substituents each independently selected from the substituent group E on the ring; (b42) isothiazolyl; (b43) a substituted isothiazolyl group having 1 to 2 substituents each independently selected from the substituent group E on the ring; (b44) thiadiazolyl; (b45) a substituted thiadiazolyl group having on its ring 1 substituent each independently selected from Substituent Group E; (b46) pyrazolyl; (b47) a substituted pyrazolyl group having 1 to 3 substituents each independently selected from Substituent Group E on the ring; (b48) triazolyl; (b49) a substituted triazole group having 1 to 2 substituents each independently selected from the substituent group E on the ring; (b50) tetrazolyl; (b51) a substituted tetrazolyl group having 1 substituent on the ring, each independently selected from Substituent Group E; (b52) benzoxazolyl; (b53) a substituted benzoxazolyl group having 1 to 4 substituents independently selected from Substituent Group E on the ring; (b54) benzothiazolyl; (b55) a substituted benzothiazolyl group having 1 to 4 substituents each independently selected from Substituent Group E on the ring; (b56)quinolinyl; (b57) a substituted quinolyl group having 1 to 6 substituents each independently selected from Substituent Group E on the ring; (b58) naphthyl; (b59) a substituted naphthyl group having 1 to 7 substituents each independently selected from Substituent Group E on the ring; (b60) tetrahydronaphthyl; (b61) a substituted tetrahydronaphthyl group having 1 to 10 substituents each independently selected from Substituent Group E on the ring; (b62) phenyl(C1-C6)alkyl; (b63) substituted phenyl (C1-C6) alkyl having 1 to 5 substituents independently selected from Substituent Group E on the ring; (b64) pyridyl(C1-C6)alkyl; (b65) a substituted pyridyl(C1-C6)alkyl group having 1 to 4 substituents independently selected from Substituent Group E on the ring; (b66) pyrazinyl(C1-C6)alkyl; (b67) a substituted pyrazinyl(C1-C6)alkyl group having 1 to 3 substituents independently selected from Substituent Group E on the ring; (b68) pyrimidinyl(C1-C6)alkyl; (b69) a substituted pyrimidinyl (C1-C6) alkyl group having 1 to 3 substituents each independently selected from Substituent Group E on the ring; (b70) furanyl (C1-C6) alkyl; (b71) a substituted furanyl (C1-C6) alkyl group having 1 to 3 substituents each independently selected from Substituent Group E on the ring; (b72) thienyl(C1-C6)alkyl; (b73) a substituted thienyl(C1-C6)alkyl group having 1 to 3 substituents independently selected from Substituent Group E on the ring; (b74) tetrahydrofuranyl (C1-C6) alkyl; (b75) a substituted tetrahydrofuranyl (C1-C6) alkyl group having 1 to 3 substituents each independently selected from Substituent Group E on the ring; (b76) benzimidazolyl; or (b77) a substituted benzimidazolyl group having 1 to 5 substituents each independently selected from Substituent Group E on the ring, R 3 express (c1) hydrogen atom; (c2)(C1-C6)alkyl; (c3)(C3-C6)cycloalkyl; (c4)(C1-C6)alkoxy; or (c5)(C1-C6)alkylcarbonyl, R 2 and R 3 can bond to each other to form a ring, X represents CH2 or an oxygen atom, Y represents an oxygen atom or a sulfur atom, Substituent group A includes: (d1) cyano; (d2) (C1-C6) alkyl; (d3) (C2-C6) alkenyl; (d4) (C2-C6) alkynyl; (d5) (C3-C6) cycloalkyl; (d6) (C1-C6) alkoxy; (d7) (C1-C6) alkylthio; (d8) (C1-C6) alkylsulfinyl; (d9) (C1-C6) alkylsulfonyl; (d10) halo(C1-C6)alkyl; (d11) halo(C3-C6)cycloalkyl; (d12) halogenated (C1-C6) alkoxy; (d13) halo(C1-C6)alkylthio; (d14) halo(C1-C6)alkylsulfinyl; (d15) halo(C1-C6)alkylsulfonyl; (d16) phenylthio; (d17) aminocarbonyl; (d18) morpholinyl; (d19) phenylcarbonyl; (d20) a substituted phenylcarbonyl group having 1 to 5 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (d21) pyrazolyl; (d22) a substituted pyrazolyl group having 1 to 3 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (d23) thienyl; and (d24) a substituted thienyl group having 1 to 3 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group on the ring, Substituent Group B includes: (e1) cyano; (e2) (C1-C6) alkyl; (e3) (C2-C6) alkenyl; (e4) (C2-C6) alkynyl; (e5) (C3-C6) cycloalkyl; (e6) (C1-C6) alkoxy; (e7) (C1-C6) alkylthio; (e8) (C1-C6) alkylsulfinyl; (e9) (C1-C6) alkylsulfonyl; (e10) halo(C1-C6)alkyl; (e11) halo(C3-C6)cycloalkyl; (e12) halogenated (C1-C6) alkoxy; (e13) halo(C1-C6)alkylthio; (e14) halo(C1-C6)alkylsulfinyl; (e15) halo(C1-C6)alkylsulfonyl; (e16) aminocarbonyl; and (e17) phenyl, Substituent group C includes: (f1) halogen atom; (f2) cyano; (f3) nitro; (f4) hydroxyl group; (f5) carboxyl group; (f6) (C1-C6) alkyl; (f7) (C2-C6) alkenyl; (f8) (C2-C6) alkynyl; (f9) (C1-C6) alkoxy; (f10) (C3-C6) cycloalkyl; (f11) (C1-C6) alkylthio; (f12) (C1-C6) alkylsulfinyl; (f13) (C1-C6) alkylsulfonyl; (f14) halo(C1-C6)alkyl; (f15) halo(C2-C6)alkenyl; (f16) halo(C2-C6)alkynyl; (f17) halogenated (C1-C6) alkoxy; (f18) halo(C3-C6)cycloalkyl; (f19) halo(C1-C6)alkylthio; (f20) halo(C1-C6)alkylsulfinyl; (f21) halo(C1-C6)alkylsulfonyl; (f22) (C1-C6) alkylcarbonyl; (f23) (C1-C6) alkoxycarbonyl; (f24) phenyl; (f25) a substituted phenyl group having 1 to 5 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (f26) phenoxy; (f27) a substituted phenoxy group having 1 to 5 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (f28) a methylenedioxy group formed by two adjacent substituents together, which may be substituted by 1 to 2 substituents selected from the group consisting of a halogen atom, a phenyl group and a (C1-C6) alkyl group; (f29) (C1-C6) alkylcarbonylamino; (f30) halo(C1-C6)alkylcarbonylamino; and (f31) (C1-C6)alkylthio (C1-C6)alkylaminocarbonyl, Substituent group D includes: (g1) a halogen atom; (g2) cyano; (g3) nitro; (g4) hydroxyl group; (g5) carboxyl group; (g6) (C1-C6) alkyl; (g7)(C2-C6)alkenyl; (g8) (C2-C6) alkynyl; (g9) (C1-C6) alkoxy; (g10) (C3-C6) cycloalkyl; (g11)(C1-C6)alkylthio; (g12) (C1-C6) alkylsulfinyl; (g13) (C1-C6) alkylsulfonyl; (g14) halo(C1-C6)alkyl; (g15) halo(C2-C6)alkenyl; (g16) halo(C2-C6)alkynyl; (g17) halogenated (C1-C6) alkoxy; (g18) halo(C3-C6)cycloalkyl; (g19) halo(C1-C6)alkylthio; (g20) halo(C1-C6)alkylsulfinyl; (g21) halo(C1-C6)alkylsulfonyl; (g22) a substituted (C3-C6)cycloalkyl group having 1 to 3 substituents on the ring, each independently selected from the group consisting of cyano, (C1-C6)alkyl, halo(C1-C6)alkyl, (C1-C6)alkoxy and (C1-C6)alkylcarbonyl; (g23) (C1-C6) alkoxy (C1-C6) alkyl; (g24) (C1-C6) alkoxy (C1-C6) alkoxy; (g25) (C1-C6) alkylcarbonylamino; (g26) halo(C1-C6)alkylcarbonylamino; (g27) (C1-C6) alkylsulfonylamino; (g28) halo(C1-C6)alkylsulfonylamino; (g29) (C1-C6) alkoxycarbonyl; (g30) N-(C1-C6)alkylaminocarbonyl; (g31) N,N-di(C1-C6)alkylaminocarbonyl; (g32) N-halo(C1-C6)alkylaminocarbonyl; (g33) N-(C1-C6)alkylaminosulfonyl; (g34) N,N-di(C1-C6)alkylaminosulfonyl; (g35) furanyl; (g36) a substituted furanyl group having 1 to 3 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (g37) oxazolyl; (g38) a substituted oxazolyl group having 1 to 2 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (g39) isoxazolyl; (g40) a substituted isoxazolyl group having 1 to 2 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (g41) oxadiazolyl; (g42) a substituted oxadiazolyl group having on the ring at least one substituent independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a halo-substituted (C1-C6) alkyl group, and a halo-substituted (C1-C6) alkoxy group; (g43) thienyl; (g44) a substituted thienyl group having 1 to 3 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a halo-substituted (C1-C6) alkyl group and a halo-substituted (C1-C6) alkoxy group; (g45) thiazolyl; (g46) a substituted thiazolyl group having 1 to 2 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (g47) isothiazolyl; (g48) a substituted isothiazolyl group having 1 to 2 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (g49) thiadiazolyl; (g50) a substituted thiadiazolyl group having on the ring one substituent each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (g51) pyrrolyl; (g52) a substituted pyrrolyl group having 1 to 3 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (g53) pyrazolyl; (g54) a substituted pyrazolyl group having 1 to 2 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (g55) imidazolyl; (g56) a substituted imidazolyl group having 1 to 2 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (g57) triazolyl; (g58) a substituted triazolyl group having on the ring one substituent each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (g59) tetrazolyl; (g60) a substituted tetrazolyl group having on the ring one substituent each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (g61) oxazolinyl; (g62) a substituted oxazolinyl group having 1 to 4 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (g63) thiazolyl; (g64) a substituted thiazolyl group having 1 to 4 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (g65) isoxazolinyl; (g66) a substituted isoxazolinyl group having 1 to 4 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (g67) isothiazolyl; (g68) a substituted isothiazolyl group having 1 to 4 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (g69) pyrrolidinyl; (g70) a substituted pyrrolidinyl group having 1 to 4 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (g71) imidazoline; (g72) a substituted imidazolinyl group having 1 to 4 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (g73) phenyl; (g74) a substituted phenyl group having 1 to 5 substituents on the ring, each of which is independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a halo-substituted (C1-C6) alkyl group and a halo-substituted (C1-C6) alkoxy group; (g75) pyridyl; (g76) a substituted pyridyl group having 1 to 4 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (g77) pyridazinyl; (g78) a substituted pyridazinyl group having 1 to 3 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (g79)pyrimidinyl; (g80) a substituted pyrimidinyl group having 1 to 3 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (g81) pyrazinyl; (g82) a substituted pyrazinyl group having 1 to 3 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (g83) triazine group; (g84) a substituted triazine group having 1 to 2 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (g85) dihydrofuranyl; (g86) dihydropyranyl; (g87) phenyloxy; (g88) a substituted phenyloxy group having 1 to 5 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (g89)phenyl(C1-C6)alkoxy; (g90) a substituted phenyl (C1-C6) alkoxy group having 1 to 5 substituents each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo (C1-C6) alkyl group and a halo (C1-C6) alkoxy group on the ring; (g91) a methylenedioxy group formed by two adjacent substituents taken together and which may be substituted by 1 to 2 substituents selected from the group consisting of a halogen atom, a phenyl group and a (C1-C6) alkyl group; and (g92)R 4 -(R 5 -N=)O=S group, where R 4 represents (C1-C6)alkyl, (C3-C6)cycloalkyl, halogenated (C1-C6)alkyl or (C1-C6)alkoxy (C1-C6)alkyl; R 5 represents a hydrogen atom, a cyano group, a (C1-C6)alkyl group, a (C3-C6)cycloalkyl group, a halogenated (C1-C6)alkyl group, a (C1-C6)alkylcarbonyl group or a halogenated (C1-C6)alkylcarbonyl group, Substituent group E includes: (h1) halogen atom; (h2) cyano; (h3) nitro; (h4) amino group; (h5) hydroxyl group; (h6) carboxyl; (h7) (C1-C6) alkyl; (h8) (C1-C6) alkoxy; (h9)(C3-C6)cycloalkyl; (h10)(C1-C6)alkylthio; (h11)(C1-C6)alkylsulfinyl; (h12) (C1-C6) alkylsulfonyl; (h13) halo(C1-C6)alkyl; (h14) halo(C1-C6)alkoxy; (h15) halo(C3-C6)cycloalkyl; (h16) halo(C1-C6)alkylthio; (h17) halo(C1-C6)alkylsulfinyl; (h18) halo(C1-C6)alkylsulfonyl; (h19) (C1-C6) alkoxycarbonyl; (h20)phenyl(C1-C6)alkoxycarbonyl; (h21) (C1-C6) alkylaminocarbonyl; (h22) N-halo(C1-C6)alkylaminocarbonyl; (h23) phenyl; (h24) a substituted phenyl group having 1 to 5 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (h25) a methylenedioxy group formed by two adjacent substituents together, which may be substituted by 1 to 2 substituents selected from the group consisting of a halogen atom and a (C1-C6) alkyl group; (h26)(C1-C6)alkylsulfonylamino; (h27) (C1-C6) alkylaminosulfonyl; (h28) (C1-C6) alkylcarbonylamino; (h29) phenoxy; (h30) a substituted phenoxy group having 1 to 5 substituents each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group on the ring; and (h31) SF5 group, Among them, R 1 The (a61) substituted aryl group and the (a63) substituted 5- to 10-membered heterocyclic group do not have a (C1-C6) alkylsulfonyl group, a halogenated (C1-C6) alkylsulfonyl group, an N-(C1-C6) alkylaminosulfonyl group, an N,N-di(C1-C6) alkylaminosulfonyl group, or an R 4 -(R 5 -N=)O=S group substitution, where R 4 represents (C1-C6)alkyl, (C3-C6)cycloalkyl, halogenated (C1-C6)alkyl or (C1-C6)alkoxy (C1-C6)alkyl; R 5 represents a hydrogen atom, a cyano group, a (C1-C6)alkyl group, a (C3-C6)cycloalkyl group, a halogenated (C1-C6)alkyl group, a (C1-C6)alkylcarbonyl group or a halogenated (C1-C6)alkylcarbonyl group, The compounds do not include compounds represented by the following structural formula:

2. The compound and salts thereof according to claim 1, wherein R 1 is (a3) ​​(C2-C6) alkynyl; (a9) a substituted (C1-C6)alkyl group having 1 to 3 substituents each independently selected from Substituent Group A; (a11) phenyl(C1-C6)alkyl, excluding phenylmethyl; (a12) a substituted phenyl (C1-C6) alkyl group having 1 to 5 substituents each independently selected from Substituent Group C on the ring; (a13) pyridyl(C1-C6)alkyl; (a14) a substituted pyridyl(C1-C6)alkyl group having 1 to 4 substituents independently selected from Substituent Group C on the ring; (a15) (C1-C6) alkylcarbonyl; (a16) halo(C1-C6)alkylcarbonyl; (a17) a substituted (C1-C6)alkylcarbonyl group having 1 to 3 substituents each independently selected from Substituent Group A; (a18) phenylcarbonyl; (a19) a substituted phenylcarbonyl group having 1 to 5 substituents each independently selected from Substituent Group C on the ring; (a20) pyridylcarbonyl; (a21) a substituted pyridylcarbonyl group having 1 to 4 substituents each independently selected from Substituent Group C on the ring; (a22) furanylcarbonyl; (a23) a substituted furanylcarbonyl group having 1 to 3 substituents each independently selected from Substituent Group C on the ring; (a24) thienylcarbonyl; (a25) a substituted thienylcarbonyl group having 1 to 3 substituents each independently selected from Substituent Group C on the ring; (a26) pyrazolylcarbonyl; (a27) a substituted pyrazolylcarbonyl group having 1 to 3 substituents each independently selected from Substituent Group C on the ring; (a28) triazolylcarbonyl; (a29) a substituted triazolylcarbonyl group having 1 to 2 substituents each independently selected from Substituent Group C on the ring; (a30) dioxodihydrodibenzofuranylcarbonyl; (a31) a substituted dioxodihydrodibenzofuranylcarbonyl group having 1 to 3 substituents each independently selected from Substituent Group C on its ring; (a32) dihydrobenzodioxinylcarbonyl; (a33) a substituted dihydrobenzodioxinylcarbonyl group having 1 to 7 substituents each independently selected from Substituent Group C on its ring; (a34) (C1-C6) alkoxycarbonyl; (a37) phenyl(C1-C6)alkoxycarbonyl; (a38) a substituted phenyl(C1-C6)alkoxycarbonyl group having 1 to 5 substituents each independently selected from Substituent Group C; (a39) (C1-C6) alkylsulfonyl; (a40) (C3-C6) cycloalkylsulfonyl; (a41) halo(C1-C6)alkylsulfonyl; (a43) a substituted (C1-C6)alkylsulfonyl group having 1 to 3 substituents each independently selected from Substituent Group A; (a45) halo(C1-C6)alkoxyhalo(C1-C6)alkylsulfonyl; (a46) phenylsulfonyl; (a47) a substituted phenylsulfonyl group having 1 to 5 substituents each independently selected from Substituent Group C; (a48) thienylsulfonyl; (a49) a substituted thienylsulfonyl group having 1 to 3 substituents each independently selected from Substituent Group C on the ring; (a50) pyrazolylsulfonyl; (a51) a substituted pyrazolylsulfonyl group having 1 to 3 substituents each independently selected from Substituent Group C on the ring; (a52) thiazolylsulfonyl; (a53) a substituted thiazolylsulfonyl group having 1 to 2 substituents each independently selected from Substituent Group C on the ring; (a54) isoxazolylsulfonyl; (a55) a substituted isoxazolylsulfonyl group having 1 to 2 substituents each independently selected from Substituent Group C on the ring; (a56) quinolylsulfonyl; (a57) a substituted quinolylsulfonyl group having 1 to 6 substituents each independently selected from Substituent Group C on the ring; (a58) phenyl(C1-C6)alkylsulfonyl; (a59) a substituted phenyl (C1-C6) alkylsulfonyl group having 1 to 5 substituents each independently selected from Substituent Group C; (a64) (C3-C6) cycloalkylcarbonyl; (a65) a substituted (C3-C6)cycloalkylcarbonyl group having 1 to 3 substituents each independently selected from Substituent Group B; (a66) isoxazolylcarbonyl; (a67) a substituted isoxazolylcarbonyl group having 1 to 2 substituents each independently selected from Substituent Group C on the ring; (a68) phenylaminocarbonyl; (a69) a substituted phenylaminocarbonyl group having 1 to 5 substituents each independently selected from Substituent Group C on the ring; (a70) pyrimidinylcarbonyl; (a71) a substituted pyrimidinylcarbonyl group having 1 to 3 substituents each independently selected from Substituent Group C on the ring; (a72) pyrazinylcarbonyl; (a73) a substituted pyrazinylcarbonyl group having 1 to 3 substituents each independently selected from Substituent Group C on the ring; (a74) pyridazinylcarbonyl; (a75) a substituted pyridazinylcarbonyl group having 1 to 3 substituents each independently selected from Substituent Group C on the ring; (a76) naphthylcarbonyl; (a77) a substituted naphthylcarbonyl group having 1 to 7 substituents each independently selected from Substituent Group C on the ring; (a78) quinolylcarbonyl; (a79) a substituted quinolylcarbonyl group having 1 to 6 substituents independently selected from Substituent Group C on the ring; (a80) a phenyl group; (a81) a substituted phenyl group having 1 to 5 substituents each independently selected from the substituent group D on the ring; (a82) pyridyl; (a83) a substituted pyridyl group having 1 to 4 substituents each independently selected from the substituent group D on the ring; (a84) pyridazinyl; (a85) a substituted pyridazinyl group having 1 to 3 substituents each independently selected from the substituent group D on the ring; (a86) pyrimidinyl; (a87) a substituted pyrimidinyl group having 1 to 3 substituents each independently selected from the substituent group D on the ring; (a88) pyrazinyl; (a89) a substituted pyrazinyl group having 1 to 3 substituents each independently selected from the substituent group D on the ring; (a90) furanyl; (a91) a substituted furanyl group having 1 to 3 substituents each independently selected from Substituent Group D on the ring; (a92) oxazolyl; (a93) substituted oxazolyl having 1 to 2 substituents each independently selected from Substituent Group D on the ring; (a94) oxadiazolyl; (a95) a substituted oxadiazolyl group having on its ring 1 substituent each independently selected from Substituent Group D; (a96) thienyl; (a97) a substituted thienyl group having 1 to 3 substituents each independently selected from the substituent group D on the ring; (a98) thiazolyl; (a99) a substituted thiazolyl group having 1 to 2 substituents each independently selected from the substituent group D on the ring; (a100) thiadiazolyl; (a101) a substituted thiadiazolyl group having on its ring at least one substituent independently selected from the substituent group D; (a102) pyrazolyl; (a103) a substituted pyrazolyl group having 1 to 3 substituents each independently selected from the substituent group D on the ring; (a104) imidazolyl; (a105) a substituted imidazolyl group having 1 to 3 substituents each independently selected from the substituent group D on the ring; (a106) triazolyl; (a107) a substituted triazole group having 1 to 2 substituents each independently selected from the substituent group D on the ring; (a108) tetrazolyl; (a109) a substituted tetrazolyl group having on its ring 1 substituent each independently selected from the substituent group D; (a110) benzoxazolyl; (a111) a substituted benzoxazolyl group having 1 to 4 substituents independently selected from the substituent group D on the ring; (a112) a benzothiazolyl group; (a113) a substituted benzothiazolyl group having 1 to 4 substituents each independently selected from the substituent group D on the ring; (a114) thiazolopyridinyl; (a115) a substituted thiazolopyridinyl group having 1 to 4 substituents each independently selected from the substituent group D on the ring; (a116) quinoxalinyl; or (a117) a substituted quinoxalyl group having 1 to 5 substituents each independently selected from the substituent group D on the ring, R 2 is (b2) (C1-C6) alkyl; (b5) (C3-C6) cycloalkyl; (b10) a substituted (C1-C6)alkyl group having 1 to 3 substituents each independently selected from Substituent Group A; (b20) phenyl; (b21) a substituted phenyl group having 1 to 5 substituents each independently selected from the substituent group E on the ring; (b22) pyridyl; (b23) a substituted pyridyl group having 1 to 4 substituents independently selected from the substituent group E on the ring; (b24) pyridazinyl; (b25) a substituted pyridazinyl group having 1 to 3 substituents each independently selected from Substituent Group E on the ring; (b26) pyrimidinyl; (b27) a substituted pyrimidinyl group having 1 to 3 substituents each independently selected from Substituent Group E on the ring; (b28) pyrazinyl; (b29) a substituted pyrazinyl group having 1 to 3 substituents each independently selected from Substituent Group E on the ring; (b34) oxazolyl; (b35) substituted oxazolyl having 1 to 2 substituents independently selected from Substituent Group E on the ring; (b36) isoxazolyl; (b37) a substituted isoxazolyl group having 1 to 2 substituents each independently selected from Substituent Group E on the ring; (b40) thiazolyl; (b41) a substituted thiazolyl group having 1 to 2 substituents each independently selected from the substituent group E on the ring; (b46) pyrazolyl; (b47) a substituted pyrazolyl group having 1 to 3 substituents each independently selected from Substituent Group E on the ring; (b56)quinolinyl; (b57) a substituted quinolyl group having 1 to 6 substituents each independently selected from Substituent Group E on the ring; (b62) phenyl(C1-C6)alkyl; (b63) substituted phenyl (C1-C6) alkyl having 1 to 5 substituents independently selected from Substituent Group E on the ring; (b70) furanyl (C1-C6) alkyl; (b71) a substituted furanyl (C1-C6) alkyl group having 1 to 3 substituents each independently selected from Substituent Group E on the ring; (b72) thienyl(C1-C6)alkyl; (b73) a substituted thienyl(C1-C6)alkyl group having 1 to 3 substituents independently selected from Substituent Group E on the ring; (b74) tetrahydrofuranyl (C1-C6) alkyl; (b75) a substituted tetrahydrofuranyl (C1-C6) alkyl group having 1 to 3 substituents each independently selected from Substituent Group E on the ring; (b76) benzimidazolyl; or (b77) a substituted benzimidazolyl group having 1 to 5 substituents each independently selected from Substituent Group E on the ring, R 3 is (c1) a hydrogen atom; (c2) (C1-C6) alkyl; or (c3)(C3-C6)cycloalkyl, R 2 and R 3 can bond to each other to form a ring, X is CH2 or an oxygen atom, Y is an oxygen atom or a sulfur atom, Substituent group A includes: (d1) cyano; (d5) (C3-C6) cycloalkyl; (d6) (C1-C6) alkoxy; (d7) (C1-C6) alkylthio; (d16) phenylthio; (d18) morpholinyl; (d19) phenylcarbonyl; (d20) a substituted phenylcarbonyl group having 1 to 5 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (d21) pyrazolyl; (d22) a substituted pyrazolyl group having 1 to 3 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (d23) thienyl; and (d24) a substituted thienyl group having 1 to 3 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group on the ring, Substituent Group B includes: (e1) cyano; (e2) (C1-C6) alkyl; and (e10) halogenated (C1-C6) alkyl, Substituent group C includes: (f1) halogen atom; (f2) cyano; (f3) nitro; (f6) (C1-C6) alkyl; (f9) (C1-C6) alkoxy; (f10) (C3-C6) cycloalkyl; (f11) (C1-C6) alkylthio; (f12) (C1-C6) alkylsulfinyl; (f13) (C1-C6) alkylsulfonyl; (f14) halo(C1-C6)alkyl; (f17) halogenated (C1-C6) alkoxy; (f19) halo(C1-C6)alkylthio; (f23) (C1-C6) alkoxycarbonyl; (f24) phenyl; (f25) a substituted phenyl group having 1 to 5 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (f26) phenoxy; (f27) a substituted phenoxy group having 1 to 5 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (f28) a methylenedioxy group formed by two adjacent substituents together, which may be substituted by 1 to 2 substituents selected from the group consisting of a halogen atom, a phenyl group and a (C1-C6) alkyl group; (f29) (C1-C6) alkylcarbonylamino; (f30) halo(C1-C6)alkylcarbonylamino; and (f31) (C1-C6)alkylthio (C1-C6)alkylaminocarbonyl, Substituent group D includes: (g1) a halogen atom; (g2) cyano; (g6) (C1-C6) alkyl; (g9) (C1-C6) alkoxy; (g11)(C1-C6)alkylthio; (g14) halo(C1-C6)alkyl; (g17) halogenated (C1-C6) alkoxy; (g19) halo(C1-C6)alkylthio; (g29) (C1-C6) alkoxycarbonyl; (g73) phenyl; and (g74) a substituted phenyl group having 1 to 5 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a halo-substituted (C1-C6) alkyl group and a halo-substituted (C1-C6) alkoxy group on the ring, Substituent group E includes: (h1) halogen atom; (h2) cyano; (h3) nitro; (h7) (C1-C6) alkyl; (h8) (C1-C6) alkoxy; (h9)(C3-C6)cycloalkyl; (h10)(C1-C6)alkylthio; (h12) (C1-C6) alkylsulfonyl; (h13) halo(C1-C6)alkyl; (h14) halo(C1-C6)alkoxy; (h16) halo(C1-C6)alkylthio; (h17) halo(C1-C6)alkylsulfinyl; (h19) (C1-C6) alkoxycarbonyl; (h21) (C1-C6) alkylaminocarbonyl; (h22) N-halo(C1-C6)alkylaminocarbonyl; (h23) phenyl; (h24) a substituted phenyl group having 1 to 5 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (h25) a methylenedioxy group formed by two adjacent substituents together, which may be substituted by 1 to 2 substituents selected from the group consisting of a halogen atom and a (C1-C6) alkyl group; (h26)(C1-C6)alkylsulfonylamino; (h27) (C1-C6) alkylaminosulfonyl; (h28) (C1-C6) alkylcarbonylamino; (h29) phenoxy; (h30) a substituted phenoxy group having 1 to 5 substituents each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group on the ring; and (h31)SF5 group.

3. The compound and salts thereof according to claim 1 or 2, wherein R 1 is (a3) ​​(C2-C6) alkynyl; (a9) a substituted (C1-C6)alkyl group having 1 to 3 substituents each independently selected from Substituent Group A; (a11) phenyl(C1-C6)alkyl, excluding phenylmethyl; (a12) a substituted phenyl (C1-C6) alkyl group having 1 to 5 substituents each independently selected from Substituent Group C on the ring; (a13) pyridyl(C1-C6)alkyl; (a14) a substituted pyridyl(C1-C6)alkyl group having 1 to 4 substituents independently selected from Substituent Group C on the ring; (a16) halo(C1-C6)alkylcarbonyl; (a17) a substituted (C1-C6)alkylcarbonyl group having 1 to 3 substituents each independently selected from Substituent Group A; (a18) phenylcarbonyl; (a19) a substituted phenylcarbonyl group having 1 to 5 substituents each independently selected from Substituent Group C on the ring; (a21) a substituted pyridylcarbonyl group having 1 to 4 substituents each independently selected from Substituent Group C on the ring; (a22) furanylcarbonyl; (a24) thienylcarbonyl; (a34) (C1-C6) alkoxycarbonyl; (a37) phenyl(C1-C6)alkoxycarbonyl; (a39) (C1-C6) alkylsulfonyl; (a40) (C3-C6) cycloalkylsulfonyl; (a41) halo(C1-C6)alkylsulfonyl; (a43) a substituted (C1-C6)alkylsulfonyl group having 1 to 3 substituents each independently selected from Substituent Group A; (a46) phenylsulfonyl; (a47) a substituted phenylsulfonyl group having 1 to 5 substituents each independently selected from Substituent Group C; (a51) a substituted pyrazolylsulfonyl group having 1 to 3 substituents each independently selected from Substituent Group C on the ring; (a56) quinolylsulfonyl; (a58) phenyl(C1-C6)alkylsulfonyl; (a59) a substituted phenyl (C1-C6) alkylsulfonyl group having 1 to 5 substituents each independently selected from Substituent Group C; (a64) (C3-C6) cycloalkylcarbonyl; (a67) a substituted isoxazolylcarbonyl group having 1 to 2 substituents each independently selected from Substituent Group C on the ring; (a69) a substituted phenylaminocarbonyl group having 1 to 5 substituents each independently selected from Substituent Group C on the ring; (a71) a substituted pyrimidinylcarbonyl group having 1 to 3 substituents each independently selected from Substituent Group C on the ring; (a73) a substituted pyrazinylcarbonyl group having 1 to 3 substituents each independently selected from Substituent Group C on the ring; (a75) a substituted pyridazinylcarbonyl group having 1 to 3 substituents each independently selected from Substituent Group C on the ring; (a76) naphthylcarbonyl; (a78) quinolylcarbonyl; (a80) phenyl; (a81) a substituted phenyl group having 1 to 5 substituents each independently selected from the substituent group D on the ring; (a82) pyridyl; (a83) a substituted pyridyl group having 1 to 4 substituents each independently selected from the substituent group D on the ring; (a84) pyridazinyl; (a85) a substituted pyridazinyl group having 1 to 3 substituents each independently selected from the substituent group D on the ring; (a86) pyrimidinyl; (a87) a substituted pyrimidinyl group having 1 to 3 substituents each independently selected from the substituent group D on the ring; (a88) pyrazinyl; (a89) a substituted pyrazinyl group having 1 to 3 substituents each independently selected from the substituent group D on the ring; (a92) oxazolyl; (a93) substituted oxazolyl having 1 to 2 substituents each independently selected from Substituent Group D on the ring; (a96) thienyl; (a97) a substituted thienyl group having 1 to 3 substituents each independently selected from the substituent group D on the ring; (a98) thiazolyl; (a99) a substituted thiazolyl group having 1 to 2 substituents each independently selected from the substituent group D on the ring; (a100) thiadiazolyl; (a101) a substituted thiadiazolyl group having on its ring at least one substituent independently selected from the substituent group D; (a102) pyrazolyl; (a103) a substituted pyrazolyl group having 1 to 3 substituents each independently selected from the substituent group D on the ring; (a108) tetrazolyl; (a109) a substituted tetrazolyl group having on its ring 1 substituent each independently selected from the substituent group D; (a110) benzoxazolyl; (a111) a substituted benzoxazolyl group having 1 to 4 substituents independently selected from the substituent group D on the ring; (a112) a benzothiazolyl group; (a113) a substituted benzothiazolyl group having 1 to 4 substituents independently selected from the substituent group D on the ring; (a114) a thiazolopyridinyl group; (a115) a substituted thiazolopyridinyl group having 1 to 4 substituents independently selected from the substituent group D on the ring; (a116) a quinoxalinyl group; or (a117) a substituted quinoxalinyl group having 1 to 5 substituents independently selected from the substituent group D on the ring, R 2 is (b2) (C1-C6) alkyl; (b5) (C3-C6) cycloalkyl; (b20) phenyl; (b21) a substituted phenyl group having 1 to 5 substituents each independently selected from the substituent group E on the ring; (b22) pyridyl; (b23) a substituted pyridyl group having 1 to 4 substituents independently selected from the substituent group E on the ring; (b24) pyridazinyl; (b25) a substituted pyridazinyl group having 1 to 3 substituents each independently selected from Substituent Group E on the ring; (b26) pyrimidinyl; (b27) a substituted pyrimidinyl group having 1 to 3 substituents each independently selected from Substituent Group E on the ring; (b28) pyrazinyl; (b29) a substituted pyrazinyl group having 1 to 3 substituents each independently selected from Substituent Group E on the ring; (b34) oxazolyl; (b37) a substituted isoxazolyl group having 1 to 2 substituents each independently selected from Substituent Group E on the ring; (b40) thiazolyl; (b41) a substituted thiazolyl group having 1 to 2 substituents each independently selected from the substituent group E on the ring; (b46) pyrazolyl; (b47) a substituted pyrazolyl group having 1 to 3 substituents each independently selected from Substituent Group E on the ring; (b56)quinolinyl; (b57) a substituted quinolyl group having 1 to 6 substituents each independently selected from Substituent Group E on the ring; (b62) phenyl(C1-C6)alkyl; (b63) substituted phenyl (C1-C6) alkyl having 1 to 5 substituents independently selected from Substituent Group E on the ring; (b70) furanyl (C1-C6) alkyl; (b71) a substituted furanyl (C1-C6) alkyl group having 1 to 3 substituents each independently selected from Substituent Group E on the ring; (b72) thienyl(C1-C6)alkyl; (b73) a substituted thienyl(C1-C6)alkyl group having 1 to 3 substituents independently selected from Substituent Group E on the ring; (b74) tetrahydrofuranyl (C1-C6) alkyl; (b75) a substituted tetrahydrofuranyl (C1-C6) alkyl group having 1 to 3 substituents each independently selected from Substituent Group E on the ring; (b76) benzimidazolyl; or (b77) a substituted benzimidazolyl group having 1 to 5 substituents each independently selected from Substituent Group E on the ring, R 3 is (c1) a hydrogen atom, X is CH2 or an oxygen atom, Y is an oxygen atom or a sulfur atom, Substituent group A includes: (d1) cyano; (d6) (C1-C6) alkoxy; (d7) (C1-C6) alkylthio; (d16) phenylthio; (d18) morpholinyl; (d20) a substituted phenylcarbonyl group having 1 to 5 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (d21) pyrazolyl; (d22) a substituted pyrazolyl group having 1 to 3 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; and (d23) thienyl, Substituent group C includes: (f1) halogen atom; (f2) cyano; (f3) nitro; (f6) (C1-C6) alkyl; (f9) (C1-C6) alkoxy; (f10) (C3-C6) cycloalkyl; (f11) (C1-C6) alkylthio; (f12) (C1-C6) alkylsulfinyl; (f13) (C1-C6) alkylsulfonyl; (f14) halo(C1-C6)alkyl; (f17) halogenated (C1-C6) alkoxy; (f19) halo(C1-C6)alkylthio; (f23) (C1-C6) alkoxycarbonyl; (f24) phenyl; (f25) a substituted phenyl group having 1 to 5 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (f26) phenoxy; (f27) a substituted phenoxy group having 1 to 5 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (f28) a methylenedioxy group formed by two adjacent substituents together, which may be substituted by 1 to 2 substituents selected from the group consisting of a halogen atom, a phenyl group and a (C1-C6) alkyl group; (f29) (C1-C6) alkylcarbonylamino group; and (f31) (C1-C6)alkylthio (C1-C6)alkylaminocarbonyl, Substituent group D includes: (g1) a halogen atom; (g2) cyano; (g6) (C1-C6) alkyl; (g9) (C1-C6) alkoxy; (g14) halo(C1-C6)alkyl; (g19) halo(C1-C6)alkylthio; (g29) (C1-C6) alkoxycarbonyl; (g73) phenyl; and (g74) a substituted phenyl group having 1 to 5 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a halo-substituted (C1-C6) alkyl group and a halo-substituted (C1-C6) alkoxy group on the ring, Substituent group E includes: (h1) halogen atom; (h2) cyano; (h3) nitro; (h7) (C1-C6) alkyl; (h8) (C1-C6) alkoxy; (h9)(C3-C6)cycloalkyl; (h10)(C1-C6)alkylthio; (h12) (C1-C6) alkylsulfonyl; (h13) halo(C1-C6)alkyl; (h14) halo(C1-C6)alkoxy; (h16) halo(C1-C6)alkylthio; (h17) halo(C1-C6)alkylsulfinyl; (h19) (C1-C6) alkoxycarbonyl; (h22) N-halo(C1-C6)alkylaminocarbonyl; (h23) phenyl; (h25) a methylenedioxy group formed by two adjacent substituents together, which may be substituted by 1 to 2 substituents selected from the group consisting of a halogen atom and a (C1-C6) alkyl group; (h26)(C1-C6)alkylsulfonylamino; (h27) (C1-C6) alkylaminosulfonyl; (h28) (C1-C6) alkylcarbonylamino; (h29) phenoxy; and (h31)SF5 group.

4. A pest control agent, characterized in that: The composition comprises the compound or salt thereof according to any one of claims 1 to 3 as an active ingredient.

5. An agricultural and horticultural pest control agent, characterized in that: The composition comprises the compound or salt thereof according to any one of claims 1 to 3 as an active ingredient.

6. An external parasite control agent for animals, characterized in that: The composition comprises the compound or salt thereof according to any one of claims 1 to 3 as an active ingredient.

7. An internal parasite control agent for animals, characterized in that: The composition comprises the compound or salt thereof according to any one of claims 1 to 3 as an active ingredient.

8. A method for controlling agricultural and horticultural pests, characterized in that: Plants or soil are treated with an effective amount of the agricultural and horticultural pest control agent according to claim 5.

9. A method for controlling external parasites of animals, characterized in that: An effective amount of the external parasite control agent for animals according to claim 6 is orally or parenterally administered to a target animal.

10. A method for controlling internal parasites of animals, characterized in that: An effective amount of the internal parasite control agent for animals according to claim 7 is orally or parenterally administered to a target animal.

11. Use of the compound or salt thereof according to any one of claims 1 to 3 as a pest control agent.

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