Aryl tetrahydropyridazine derivatives or their salts, insecticides containing the same and methods of use thereof

Abstract

In crop production such as agriculture and horticulture, the damage caused by pests is still large. Due to the emergence of pests resistant to existing drugs, it is expected to develop new pesticides for agriculture and horticulture. The present invention has found that the general formula (1) {wherein, X and Y represent oxygen atoms or sulfur atoms, R 1 represents a hydrogen atom, etc., R 2 represents substituted phenyl, etc., R 3 represents a hydrogen atom, etc., R 4 A compound represented by {representing a substituted phenyl group, etc.} or a salt thereof exhibits a high insecticidal effect against pests in the agronomic and horticultural fields, and provides an agronomic and horticultural insecticide containing the compound as an active ingredient and a method for using the compound.

Description

Technical Field

[0001] The present invention relates to aryl tetrahydropyridazine derivatives or their salts, and insecticides containing the compounds as active ingredients and methods of using the same. Background Art

[0002] Patent Document 1 reports that certain tetrahydropyridazine-3,5-dione derivatives are useful as pharmaceutical compounds. However, this document does not disclose or suggest that the compounds are useful as insecticides.

[0003] Prior art literature

[0004] Patent Literature

[0005] Patent Document 1: International Publication No. 2014 / 142273 Pamphlet Summary of the invention

[0006] Technical problem solved by the invention

[0007] In crop production such as agriculture and horticulture, damage caused by pests and the like is still significant, and the development of new insecticides and acaricides is desired due to the emergence of pests resistant to existing drugs and the like.

[0008] Technical means of solving problems

[0009] As a result of intensive studies to develop new insecticides, particularly insecticides for agricultural and horticultural use, the present inventors have discovered that compounds represented by the general formula (1) of the present invention or salts thereof having an aryl tetrahydropyridazine derivative at the carboxylic acid site as a carboxamide exhibit excellent effects as insecticides, thereby completing the present invention.

[0010] That is, the present invention is as follows.

[0011] [1] A compound represented by the general formula (1) and a salt thereof,

[0012] General formula (1)

[0013] [Chemical formula 1]

[0014]

[0015] {In the formula, R 1represents (a1) a hydrogen atom; (a2) a (C1-C6) alkyl group; (a3) ​​a (C2-C6) alkenyl group; (a4) a (C2-C6) alkynyl group; (a5) a (C3-C6) cycloalkyl group; (a6) a (C1-C6) alkoxy group; (a7) a halogenated (C1-C6) alkyl group; (a8) a (C1-C6) alkylcarbonyl group; (a9) a (C1-C6) alkoxycarbonyl group; (a10) a alkyl group having a cyano group, a (C1-C6) alkoxy group and a (C3-C6) alkoxy group on the chain, respectively. (a11) substituted (C1-C6)alkyl having 1 to 3 substituents in the (C1-C6)cycloalkyl group; (a12) substituted thiazolylmethyl having 1 to 2 substituents on the ring independently selected from halogen atoms, (C1-C6)alkyl and (C1-C6)alkoxy groups; (a13) benzyl; or (a14) substituted benzyl having 1 to 3 substituents on the ring independently selected from halogen atoms, (C1-C6)alkyl and (C1-C6)alkoxy groups.

[0016] R 2 represents (b1) an aryl group; (b2) a substituted aryl group having one or more substituents independently selected from the substituent group A on the ring; (b3) a 5- to 10-membered heterocyclic group; or (b4) a substituted 5- to 10-membered heterocyclic group having one or more substituents independently selected from the substituent group A on the ring.

[0017] Among them, R 2 In the tetrahydropyridazine ring, the atoms adjacent to the atoms bonded to the tetrahydropyridazine ring are unsubstituted (C1-C6) alkylsulfonyl, halogenated (C1-C6) alkylsulfonyl, N-(C1-C6) alkylaminosulfonyl, N,N-di(C1-C6) alkylaminosulfonyl and R 6 -(R 7 -N=)O=S group (where R 6 represents (C1-C6)alkyl, (C3-C6)cycloalkyl, halogenated (C1-C6)alkyl or (C1-C6)alkoxy (C1-C6)alkyl, R 7 represents a hydrogen atom, a cyano group, a (C1-C6)alkyl group, a (C3-C6)cycloalkyl group, a halogenated (C1-C6)alkyl group, a (C2-C6)alkylcarbonyl group or a halogenated (C2-C6)alkylcarbonyl group),

[0018] R 3 represents (c1) a hydrogen atom; (c2) a (C1-C6) alkyl group; (c3) a (C3-C6) cycloalkyl group; (c4) a (C1-C6) alkoxy group; or (c5) a (C1-C6) alkylcarbonyl group.

[0019] R 4represents (d1) (C1-C6) alkyl; (d2) (C2-C6) alkenyl; (d3) (C2-C6) alkynyl; (d4) (C3-C6) cycloalkyl; (d5) halogenated (C1-C6) alkyl; (d6) halogenated (C2-C6) alkenyl; (d7) halogenated (C2-C6) alkynyl; (d8) substituted (C1-C6) alkyl having 1 to 3 substituents independently selected from substituent group B; (d9) substituted (C3-C6) cycloalkyl having 1 to 3 substituents independently selected from substituent group C on the ring; (d10) (C1-C6) alkylsulfonyl; (d11) N-(C1-C6) alkylaminosulfonyl; (d12) phenyl; (d13) substituted (C1-C6) alkyl having 1 to 3 substituents independently selected from substituent group C on the ring; Substituted phenyl having 1 to 5 substituents selected from the substituent group D; (d14) phenyl (C1-C6) alkyl; (d15) substituted phenyl (C1-C6) alkyl having 1 to 5 substituents independently selected from the substituent group D on the ring; (d16) pyridyl; (d17) substituted pyridyl having 1 to 4 substituents independently selected from the substituent group D on the ring; (d18) pyridazinyl; (d19) substituted pyridazinyl having 1 to 3 substituents independently selected from the substituent group D on the ring; (d20) pyrimidinyl; (d21) substituted pyrimidinyl having 1 to 3 substituents independently selected from the substituent group D on the ring; (d22) pyrazinyl; (d23) substituted 1 to 2 substituents independently selected from the substituent group D on the ring substituted pyrazinyl having 3 substituents; (d24) pyrazolyl; (d25) substituted pyrazolyl having 1 to 3 substituents independently selected from the substituent group D on the ring; (d26) isoxazolyl; (d27) substituted isoxazolyl having 1 to 2 substituents independently selected from the substituent group D on the ring; (d28) isothiazolyl; (d29) substituted isothiazolyl having 1 to 2 substituents independently selected from the substituent group D on the ring; (d30) oxazolyl; (d31) substituted oxazolyl having 1 to 2 substituents independently selected from the substituent group D on the ring; (d32) thiazolyl; (d33) substituted thiazolyl having 1 to 2 substituents independently selected from the substituent group D on the ring; (d34) triazolyl; (d35) substituted triazolyl having 1 to 2 substituents independently selected from the substituent group D on the ring; (d36) thiadiazolyl; (d37) substituted thiadiazolyl having 1 substituent independently selected from the substituent group D on the ring; (d38) tetrazolyl; (d39) substituted tetrazolyl having 1 substituent independently selected from the substituent group D on the ring; (d40) triazinyl; (d41) substituted triazinyl having 1 to 2 substituents independently selected from the substituent group D on the ring; (d42) furanyl (C1-C6) alkyl; (d43) substituted furanyl (C1-C6) alkyl having 1 to 3 substituents independently selected from the substituent group D on the ring; (d44) thienyl (C1-C6) alkyl;(d45) substituted thienyl (C1-C6) alkyl having 1 to 3 substituents independently selected from the substituent group D on the ring; (d46) quinolyl; (d47) substituted quinolyl having 1 to 6 substituents independently selected from the substituent group D on the ring; (d48) benzothiazolyl; (d49) substituted benzothiazolyl having 1 to 4 substituents independently selected from the substituent group D on the ring; (d50) pyridyl (C1-C6) alkyl; (d51) substituted thienyl (C1-C6) alkyl having 1 to 3 substituents independently selected from the substituent group D on the ring; (d52) pyrazinyl (C1-C6) alkyl; (d53) substituted pyrazinyl (C1-C6) alkyl having 1 to 3 substituents independently selected from Substituent Group D on the ring; (d54) naphthyl; (d55) substituted naphthyl having 1 to 7 substituents independently selected from Substituent Group D on the ring; (d56) tetrahydronaphthyl; or (d57) substituted tetrahydronaphthyl having 1 to 10 substituents independently selected from Substituent Group D on the ring. ;

[0020] X and Y each independently represent an oxygen atom or a sulfur atom.

[0021] Substituent group A includes (e1) a halogen atom; (e2) a cyano group; (e3) a nitro group; (e4) a hydroxyl group; (e5) a carboxyl group; (e6) a (C1-C6) alkyl group; (e7) a (C2-C6) alkenyl group; (e8) a (C2-C6) alkynyl group; (e9) a (C1-C6) alkoxy group; (e10) a (C3-C6) cycloalkyl group; (e11) a (C1-C6) alkylthio group; (e12) a (C1-C6) alkylsulfinyl group; (e13) a (C1-C6) alkylsulfonyl group; (e14) a halogenated (C1-C6) alkyl group; ( e15) halo (C2-C6) alkenyl; (e16) halo (C2-C6) alkynyl; (e17) halo (C1-C6) alkoxy; (e18) halo (C3-C6) cycloalkyl; (e19) halo (C1-C6) alkylthio; (e20) halo (C1-C6) alkylsulfinyl; (e21) halo (C1-C6) alkylsulfonyl; (e22) (C1-C6) alkylcarbonylamino; (e23) halo (C1-C6) alkylcarbonylamino; (e24) (C1-C6) alkylsulfonylamino; (e25) halo (C1-C6) alkylsulfonylamino; (e26) SF5 group; (e27) (C1-C6) alkoxy (C1-C6) alkyl; (e28) N-(C1-C6) alkylcarboxamide; (e29) N-halo (C1-C6) alkylcarboxamide; (e30) oxadiazolyl; (e31) having on the ring independently selected from halogen atoms, cyano, (C1-C6) alkyl, (C1-C6) alkoxy, (C3-C6) cycloalkyl, (C1-C6) alkylthio, (C1-C6) alkylthio substituted oxadiazolyl with one substituent selected from sulfonyl, (C1-C6)alkylsulfonyl, halo(C1-C6)alkyl and halo(C1-C6)alkoxy; (e32) (C1-C6)alkoxycarbonyl; (e33) methylenedioxy optionally substituted with one to two substituents selected from halogen atoms, phenyl and (C1-C6)alkyl, formed by two adjacent substituents; (e34) N-(C1-C6)alkylaminosulfonyl; (e35) N,N-di(C1-C6)alkylaminosulfonyl; (e36) R 6 -(R 7 -N=)O=S group (where R 6 represents (C1-C6)alkyl, (C3-C6)cycloalkyl, halogenated (C1-C6)alkyl or (C1-C6)alkoxy (C1-C6)alkyl, R 7represents a hydrogen atom, a cyano group, a (C1-C6) alkyl group, a (C3-C6) cycloalkyl group, a halogenated (C1-C6) alkyl group, a (C2-C6) alkylcarbonyl group or a halogenated (C2-C6) alkylcarbonyl group); and (e37) a substituted (C3-C6) cycloalkyl group having 1 to 3 substituents on the ring independently selected from a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group and a (C1-C6) alkylcarbonyl group.

[0022] Substituent Group B includes (f1) cyano; (f2) (C3-C6) cycloalkyl; (f3) (C1-C6) alkoxy; (f4) (C1-C6) alkylthio; (f5) (C1-C6) alkylsulfinyl; (f6) (C1-C6) alkylsulfonyl; (f7) halo (C3-C6) cycloalkyl; (f8) halo (C1-C6) alkoxy; (f9) halo (C1-C6) alkylthio; (f10) halo (C1-C6) alkylsulfinyl; (f11) halo (C1-C6) alkylsulfonyl; (f12) carboxamide; and (f13) phenylcarbonyl.

[0023] Substituent Group C includes (g1) cyano; (g2) (C1-C6) alkyl; (g3) (C3-C6) cycloalkyl; (g4) (C1-C6) alkoxy; (g5) (C1-C6) alkylthio; (g6) (C1-C6) alkylsulfinyl; (g7) (C1-C6) alkylsulfonyl; (g8) halogenated (C3-C6) cycloalkyl; (g9) halogenated (C1-C6) alkoxy; (g10) halogenated (C1-C6) alkylthio; (g11) halogenated (C1-C6) alkylsulfinyl; (g12) halogenated (C1-C6) alkylsulfonyl; (g13) halogenated (C1-C6) alkyl; (g14) carboxamido; (g15) (C2-C6) alkynyl; and (g16) phenyl.

[0024] The substituent group D includes (h1) a halogen atom; (h2) a cyano group; (h3) a hydroxyl group; (h4) a carboxyl group; (h5) a (C1-C6) alkyl group; (h6) a (C1-C6) alkoxy group; (h7) a (C3-C6) cycloalkyl group; (h8) a (C1-C6) alkylthio group; (h9) a (C1-C6) alkylsulfinyl group; (h10) a (C1-C6) alkylsulfonyl group; (h11) a halo (C1-C6) alkyl group; (h12) a halo (C1-C6) alkoxy group; (h13) a halo (C3-C6) cycloalkyl group; (h14) a halo (C1-C6) ) alkylthio; (h15) halogenated (C1-C6) alkylsulfinyl; (h16) halogenated (C1-C6) alkylsulfonyl; (h17) (C1-C6) alkoxycarbonyl; (h18) N-(C1-C6) alkylcarboxamide; (h19) N-halogenated (C1-C6) alkylcarboxamide; (h20) methylenedioxy optionally substituted with 1 to 2 substituents selected from halogen atoms, phenyl and (C1-C6) alkyl, obtained by combining two adjacent substituents; (h21) nitro; (h22) amino; and (h23) benzyloxycarbonyl.}

[0025] [2] The compound and salt thereof according to [1], wherein

[0026] R 1 , R 3 , R 4 , X, Y, substituent groups A, B, C and D are the same as in [1],

[0027] R 2(b5) phenyl; (b6) substituted phenyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b7) pyridyl; (b8) substituted pyridyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b9) pyridazinyl; (b10) substituted pyridazinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b11) pyrimidinyl; (b12) substituted pyrimidinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b13) pyrazinyl; (b14) substituted pyrazinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b15) furanyl; (b16) (b17) substituted furanyl having 1 to 3 substituents from Substituent Group A; (b18) substituted thienyl having 1 to 3 substituents independently selected from Substituent Group A on the ring; (b19) isoxazolyl; (b20) substituted isoxazolyl having 1 to 2 substituents independently selected from Substituent Group A on the ring; (b21) oxazolyl; (b22) substituted oxazolyl having 1 to 2 substituents independently selected from Substituent Group A on the ring; (b23) pyrazolyl; (b24) substituted pyrazolyl having 1 to 3 substituents independently selected from Substituent Group A on the ring; (b25) imidazolyl; (b26) substituted imidazole having 1 to 3 substituents independently selected from Substituent Group A on the ring (b27) triazolyl; (b28) substituted triazolyl having 1 to 2 substituents independently selected from the substituent group A on the ring; (b29) thiazolyl; (b30) substituted thiazolyl having 1 to 2 substituents independently selected from the substituent group A on the ring; (b31) isothiazolyl; (b32) substituted isothiazolyl having 1 to 2 substituents independently selected from the substituent group A on the ring; (b33) thiadiazolyl; (b34) substituted thiadiazolyl having 1 substituent independently selected from the substituent group A on the ring; (b35) imidazopyridinyl; (b36) substituted imidazopyridinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b37) quinoxalinyl ; (b38) substituted quinoxalinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b39) benzoxazolyl; (b40) substituted benzoxazolyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b41) benzimidazolyl; (b42) substituted benzimidazolyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b43) benzothiazolyl; (b44) substituted benzothiazolyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b45) thiazolopyridinyl; (b46) substituted thiazolopyridinyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b47) quinolyl;(b48) substituted quinolyl having 1 to 6 substituents independently selected from the substituent group A on the ring; (b49) naphthyl; (b50) substituted naphthyl having 1 to 7 substituents independently selected from the substituent group A on the ring; (b51) triazine; (b52) substituted triazine having 1 to 2 substituents independently selected from the substituent group A on the ring; (b53) pyrrolyl; (b54) substituted pyrrolyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b55) tetrazolyl; (b56) substituted tetrazolyl having 1 substituent independently selected from the substituent group A on the ring; (b57) oxadiazolyl; (b58) 1 substituent independently selected from the substituent group A on the ring (b59) 2-oxopyridyl; (b60) substituted 2-oxopyridyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b61) benzofuranyl; (b62) substituted benzofuranyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b63) benzisoxazolyl; (b64) substituted benzisoxazolyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b65) benzothienyl; (b66) substituted benzothienyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b67) benzisothiazolyl; (b68) substituted 1 to 4 substituents independently selected from the substituent group A on the ring (b69) indolyl; (b70) substituted indolyl having 1 to 6 substituents independently selected from substituent group A on the ring; (b71) isoindolyl; (b72) substituted isoindolyl having 1 to 6 substituents independently selected from substituent group A on the ring; (b73) indazolyl; (b74) substituted indazolyl having 1 to 5 substituents independently selected from substituent group A on the ring; (b75) benzotriazolyl; (b76) substituted benzotriazolyl having 1 to 4 substituents independently selected from substituent group A on the ring; (b77) furanopyridinyl; (b78) substituted furanopyridinyl having 1 to 4 substituents independently selected from substituent group A on the ring; b79) thienopyridinyl; (b80) substituted thienopyridinyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b81) indolizinyl; (b82) substituted indolizinyl having 1 to 6 substituents independently selected from the substituent group A on the ring; (b83) pyrrolopyridinyl; (b84) substituted pyrrolopyridinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b85) pyrrolopyrimidinyl; (b86) substituted pyrrolopyrimidinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b87) oxazolopyridinyl; (b88) substituted oxazolopyridinyl having 1 to 3 substituents independently selected from the substituent group A on the ring;(b89) isoxazolopyridinyl; (b90) substituted isoxazolopyridinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b91) isothiazolopyridinyl; (b92) substituted isothiazolopyridinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b93) imidazopyrimidinyl; (b94) substituted imidazopyrimidinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b95) pyrazolopyridinyl; (b96) substituted pyrazolopyridinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b97) pyrazolopyrimidinyl; (b98) substituted pyrazolopyrimidinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b99) triazolopyridinyl; (b100) substituted pyrazolopyridinyl having 1 to 4 substituents independently selected from the substituent group A on the ring Substituted triazolopyridinyl; (b101) triazolopyrimidinyl; (b102) substituted triazolopyrimidinyl having 1 to 4 substituents independently selected from substituent group A on the ring; (b103) isoquinolyl; (b104) substituted isoquinolyl having 1 to 6 substituents independently selected from substituent group A on the ring; (b105) oxazinyl; (b106) substituted triazolopyrimidinyl having 1 to 5 substituents independently selected from substituent group A on the ring substituted oxazinyl; (b107) phthalazinyl; (b108) substituted phthalazinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b109) quinazolinyl; (b110) substituted quinazolinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b111) naphthyridinyl; or (b112) substituted naphthyridinyl having 1 to 5 substituents independently selected from the substituent group A on the ring. ;

[0028] [3] The compound or salt thereof according to [1] or [2], wherein

[0029] R 1 is (a1) a hydrogen atom; (a2) a (C1-C6) alkyl group; or (a4) a (C2-C6) alkynyl group,

[0030] R 2(b5) phenyl; (b6) substituted phenyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b7) pyridyl; (b8) substituted pyridyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b9) pyridazinyl; (b10) substituted pyridazinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b11) pyrimidinyl; (b12) substituted pyrimidinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b13) pyrazinyl; (b14) substituted pyrazinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b15) furanyl; (b16) (b17) substituted furanyl having 1 to 3 substituents from Substituent Group A; (b18) substituted thienyl having 1 to 3 substituents independently selected from Substituent Group A on the ring; (b19) isoxazolyl; (b20) substituted isoxazolyl having 1 to 2 substituents independently selected from Substituent Group A on the ring; (b21) oxazolyl; (b22) substituted oxazolyl having 1 to 2 substituents independently selected from Substituent Group A on the ring; (b23) pyrazolyl; (b24) substituted pyrazolyl having 1 to 3 substituents independently selected from Substituent Group A on the ring; (b25) imidazolyl; (b26) substituted imidazole having 1 to 3 substituents independently selected from Substituent Group A on the ring (b27) triazolyl; (b28) substituted triazolyl having 1 to 2 substituents independently selected from the substituent group A on the ring; (b29) thiazolyl; (b30) substituted thiazolyl having 1 to 2 substituents independently selected from the substituent group A on the ring; (b31) isothiazolyl; (b32) substituted isothiazolyl having 1 to 2 substituents independently selected from the substituent group A on the ring; (b33) thiadiazolyl; (b34) substituted thiadiazolyl having 1 substituent independently selected from the substituent group A on the ring; (b35) imidazopyridinyl; (b36) substituted imidazopyridinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b37) quinoxalinyl ; (b38) substituted quinoxalinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b39) benzoxazolyl; (b40) substituted benzoxazolyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b41) benzimidazolyl; (b42) substituted benzimidazolyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b43) benzothiazolyl; (b44) substituted benzothiazolyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b45) thiazolopyridinyl; (b46) substituted thiazolopyridinyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b47) quinolyl;or (b48) a substituted quinolyl group having 1 to 6 substituents independently selected from Substituent Group A on the ring;

[0031] R 3 is (c1) a hydrogen atom; or (c2) a (C1-C6) alkyl group,

[0032] R 4(d1) (C1-C6) alkyl; (d2) (C2-C6) alkenyl; (d3) (C2-C6) alkynyl; (d4) (C3-C6) cycloalkyl; (d5) halogenated (C1-C6) alkyl; (d8) substituted (C1-C6) alkyl having 1 to 3 substituents independently selected from substituent group B; (d9) substituted (C3-C6) cycloalkyl having 1 to 3 substituents independently selected from substituent group C on the ring; (d10) (C1-C6) alkylsulfonyl; (d11) N-(C1-C6) alkylaminosulfonyl; (d12) phenyl; (d13) substituted phenyl having 1 to 5 substituents independently selected from substituent group D on the ring; (d14 )phenyl(C1-C6)alkyl; (d15) substituted phenyl(C1-C6)alkyl having 1 to 5 substituents independently selected from the substituent group D on the ring; (d16) pyridyl; (d17) substituted pyridyl having 1 to 4 substituents independently selected from the substituent group D on the ring; (d18) pyridazinyl; (d19) substituted pyridazinyl having 1 to 3 substituents independently selected from the substituent group D on the ring; (d20) pyrimidinyl; (d21) substituted pyrimidinyl having 1 to 3 substituents independently selected from the substituent group D on the ring; (d22) pyrazinyl; (d23) substituted pyrazinyl having 1 to 3 substituents independently selected from the substituent group D on the ring; (d24) Pyrazolyl; (d25) substituted pyrazolyl having 1 to 3 substituents independently selected from the substituent group D on the ring; (d26) isoxazolyl; (d27) substituted isoxazolyl having 1 to 2 substituents independently selected from the substituent group D on the ring; (d28) isothiazolyl; (d29) substituted isothiazolyl having 1 to 2 substituents independently selected from the substituent group D on the ring; (d30) oxazolyl; (d31) substituted oxazolyl having 1 to 2 substituents independently selected from the substituent group D on the ring; (d32) thiazolyl; (d33) substituted thiazolyl having 1 to 2 substituents independently selected from the substituent group D on the ring; (d34) triazolyl; (d35) Substituted triazolyl having 1 to 2 substituents independently selected from the substituent group D; (d36) thiadiazolyl; (d37) substituted thiadiazolyl having 1 substituent independently selected from the substituent group D on the ring; (d38) tetrazolyl; (d39) substituted tetrazolyl having 1 substituent independently selected from the substituent group D on the ring; (d40) triazinyl; (d41) substituted triazinyl having 1 to 2 substituents independently selected from the substituent group D on the ring; (d42) furanyl (C1-C6) alkyl; (d43) substituted furanyl (C1-C6) alkyl having 1 to 3 substituents independently selected from the substituent group D on the ring; (d44) thienyl (C1-C6) alkyl;(d45) substituted thienyl (C1-C6) alkyl having 1 to 3 substituents independently selected from the substituent group D on the ring; (d46) quinolyl; (d47) substituted quinolyl having 1 to 6 substituents independently selected from the substituent group D on the ring; (d48) benzothiazolyl; (d49) substituted benzothiazolyl having 1 to 4 substituents independently selected from the substituent group D on the ring; (d50) pyridyl (C1-C6) alkyl; (d51) substituted pyridyl(C1-C6)alkyl having 1 to 4 substituents; (d52) pyrazinyl(C1-C6)alkyl; (d53) substituted pyrazinyl(C1-C6)alkyl having 1 to 3 substituents independently selected from Substituent Group D on the ring; (d54) naphthyl; (d55) substituted naphthyl having 1 to 7 substituents independently selected from Substituent Group D on the ring; (d56) tetrahydronaphthyl; or (d57) substituted tetrahydronaphthyl having 1 to 10 substituents independently selected from Substituent Group D on the ring;

[0033] Substituent group A includes (e1) a halogen atom; (e2) a cyano group; (e4) a hydroxyl group; (e5) a carboxyl group; (e6) a (C1-C6) alkyl group; (e9) a (C1-C6) alkoxy group; (e10) a (C3-C6) cycloalkyl group; (e11) a (C1-C6) alkylthio group; (e12) a (C1-C6) alkylsulfinyl group; (e13) a (C1-C6) alkylsulfonyl group; (e14) a halogenated (C1-C6) alkyl group -C6) alkyl; (e17) halo (C1-C6) alkoxy; (e18) halo (C3-C6) cycloalkyl; (e19) halo (C1-C6) alkylthio; (e20) halo (C1-C6) alkylsulfinyl; (e21) halo (C1-C6) alkylsulfonyl; (e22) (C1-C6) alkylcarbonylamino; (e24) (C1-C6) alkylsulfonylamino; (e28) N-(C1-C6)alkylcarboxamide; (e30)oxadiazolyl; (e31) having on the ring independently selected from halogen atoms, cyano, (C1-C6)alkyl, (C1-C6)alkoxy, (C3-C6)cycloalkyl, (C1-C6)alkylthio, (C1-C6)alkylsulfinyl, (C1-C6)alkylsulfonyl, halo (C1-C6)alkyl and halo (C1-C6)alkoxy (e32) (C1-C6) alkoxycarbonyl; (e33) a methylenedioxy group optionally substituted with one or two substituents selected from halogen atoms, phenyl and (C1-C6) alkyl, formed by two adjacent substituents; (e34) N-(C1-C6) alkylaminosulfonyl; (e35) N,N-di(C1-C6) alkylaminosulfonyl; (e36) R 6 -(R 7-N=)O=S group (where R 6 represents (C1-C6)alkyl, (C3-C6)cycloalkyl, halogenated (C1-C6)alkyl or (C1-C6)alkoxy (C1-C6)alkyl, R 7 represents a hydrogen atom, a cyano group, a (C1-C6) alkyl group, a (C3-C6) cycloalkyl group, a halogenated (C1-C6) alkyl group, a (C2-C6) alkylcarbonyl group or a halogenated (C2-C6) alkylcarbonyl group); and (e37) a substituted (C3-C6) cycloalkyl group having 1 to 3 substituents independently selected from a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group and a (C1-C6) alkylcarbonyl group on the ring,

[0034] Substituent Group B comprises (f1) cyano; (f2) (C3-C6) cycloalkyl; (f3) (C1-C6) alkoxy; (f4) (C1-C6) alkylthio; (f5) (C1-C6) alkylsulfinyl; (f6) (C1-C6) alkylsulfonyl; (f7) halo (C3-C6) cycloalkyl; (f8) halo (C1-C6) alkoxy; (f9) halo (C1-C6) alkylthio; (f10) halo (C1-C6) alkylsulfinyl; and (f11) halo (C1-C6) alkylsulfonyl,

[0035] Substituent Group C comprises (g1) cyano; (g2) (C1-C6) alkyl; (g3) (C3-C6) cycloalkyl; (g4) (C1-C6) alkoxy; (g5) (C1-C6) alkylthio; (g6) (C1-C6) alkylsulfinyl; (g7) (C1-C6) alkylsulfonyl; (g8) halogenated (C3-C6) cycloalkyl; (g9) halogenated (C1-C6) alkoxy; (g10) halogenated (C1-C6) alkylthio; (g11) halogenated (C1-C6) alkylsulfinyl; (g12) halogenated (C1-C6) alkylsulfonyl; (g13) halogenated (C1-C6) alkyl; (g15) (C2-C6) alkynyl; and (g16) phenyl,

[0036] The substituent group D includes (h1) a halogen atom; (h2) a cyano group; (h3) a hydroxyl group; (h4) a carboxyl group; (h5) a (C1-C6) alkyl group; (h6) a (C1-C6) alkoxy group; (h7) a (C3-C6) cycloalkyl group; (h8) a (C1-C6) alkylthio group; (h9) a (C1-C6) alkylsulfinyl group; (h10) a (C1-C6) alkylsulfonyl group; (h11) a halo (C1-C6) alkyl group; (h12) a halo (C1-C6) alkoxy group; (h13) a halo (C3-C6) cycloalkyl group; (h h14) halo(C1-C6)alkylthio; (h15) halo(C1-C6)alkylsulfinyl; (h16) halo(C1-C6)alkylsulfonyl; (h17) (C1-C6)alkoxycarbonyl; (h18) N-(C1-C6)alkylcarboxamide; (h20) methylenedioxy group formed by two adjacent substituents, optionally substituted with 1 or 2 substituents selected from halogen atoms, phenyl and (C1-C6)alkyl; (h21) nitro; (h22) amino; and (h23) benzyloxycarbonyl.

[0037] [4] The compound or salt thereof according to any one of [1] to [3], wherein

[0038] R 1 is (a1) a hydrogen atom,

[0039] R 2(b5) phenyl; (b6) substituted phenyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b7) pyridyl; (b8) substituted pyridyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b9) pyridazinyl; (b10) substituted pyridazinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b11) pyrimidinyl; (b12) substituted pyrimidinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b13) pyrazinyl; (b14) substituted pyrazinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b23) pyrazolyl; (b24) substituted pyrazolyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b27) triazolyl ; (b28) a substituted triazolyl group having 1 to 2 substituents independently selected from the substituent group A on the ring; (b29) a thiazolyl group; (b30) a substituted thiazolyl group having 1 to 2 substituents independently selected from the substituent group A on the ring; (b33) a thiadiazolyl group; (b34) a substituted thiadiazolyl group having 1 substituent independently selected from the substituent group A on the ring; (b43) a benzothiazolyl group; (b44) a substituted benzothiazolyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b45) a thiazolopyridyl group; (b46) a substituted thiazolopyridyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b47) a quinolyl group; or (b48) a substituted quinolyl group having 1 to 6 substituents independently selected from the substituent group A on the ring,

[0040] R 3 is (c1) a hydrogen atom; or (c2) a (C1-C6) alkyl group,

[0041] R 4(d1) (C1-C6) alkyl; (d2) (C2-C6) alkenyl; (d3) (C2-C6) alkynyl; (d4) (C3-C6) cycloalkyl; (d5) halogenated (C1-C6) alkyl; (d8) substituted (C1-C6) alkyl having 1 to 3 substituents independently selected from substituent group B; (d9) substituted (C3-C6) cycloalkyl having 1 to 3 substituents independently selected from substituent group C on the ring; (d12) phenyl; (d13) substituted phenyl having 1 to 5 substituents independently selected from substituent group D on the ring; (d14) phenyl (C1-C6) alkyl; (d15) substituted (C1-C6) alkyl having 1 to 5 substituents independently selected from substituent group D on the ring (d16) pyridyl; (d17) substituted pyridyl having 1 to 4 substituents independently selected from the substituent group D on the ring; (d18) pyridazinyl; (d19) substituted pyridazinyl having 1 to 3 substituents independently selected from the substituent group D on the ring; (d20) pyrimidinyl; (d21) substituted pyrimidinyl having 1 to 3 substituents independently selected from the substituent group D on the ring; (d22) pyrazinyl; (d24) pyrazolyl; (d25) substituted pyrazolyl having 1 to 3 substituents independently selected from the substituent group D on the ring; (d26) isoxazolyl; (d27) substituted isoxazolyl having 1 to 2 substituents independently selected from the substituent group D on the ring (d32) thiazolyl; (d33) substituted thiazolyl having 1 to 2 substituents independently selected from the substituent group D on the ring; (d34) triazolyl; (d35) substituted triazolyl having 1 to 2 substituents independently selected from the substituent group D on the ring; (d36) thiadiazolyl; (d37) substituted thiadiazolyl having 1 substituent independently selected from the substituent group D on the ring; (d42) furanyl (C1-C6) alkyl; (d43) substituted furanyl (C1-C6) alkyl having 1 to 3 substituents independently selected from the substituent group D on the ring; (d44) thienyl (C1-C6) alkyl; (d45) substituted 1 to 3 substituents independently selected from the substituent group D on the ring (d46) quinolyl; (d47) substituted quinolyl having 1 to 6 substituents independently selected from the substituent group D on the ring; (d48) benzothiazolyl; (d49) substituted benzothiazolyl having 1 to 4 substituents independently selected from the substituent group D on the ring; (d50) pyridyl (C1-C6) alkyl; (d51) substituted pyridyl (C1-C6) alkyl having 1 to 4 substituents independently selected from the substituent group D on the ring; (d52) pyrazinyl (C1-C6) alkyl; (d53) substituted pyrazinyl (C1-C6) alkyl having 1 to 3 substituents independently selected from the substituent group D on the ring; (d54) naphthyl;(d55) substituted naphthyl having 1 to 7 substituents independently selected from Substituent Group D on the ring; (d56) tetrahydronaphthyl; or (d57) substituted tetrahydronaphthyl having 1 to 10 substituents independently selected from Substituent Group D on the ring;

[0042] Substituent Group A comprises (e1) a halogen atom; (e2) a cyano group; (e6) a (C1-C6) alkyl group; (e9) a (C1-C6) alkoxy group; (e11) a (C1-C6) alkylthio group; (e12) a (C1-C6) alkylsulfinyl group; (e13) a (C1-C6) alkylsulfonyl group; (e14) a halo (C1-C6) alkyl group; (e17) a halo (C1-C6) alkoxy group; (e19) a halo (C1-C6) alkylthio group; (e21) a halo (C1-C6) alkylsulfonyl group; (e32) a (C1-C6) alkoxycarbonyl group; (e34) an N-(C1-C6) alkylaminosulfonyl group; and (e35) an N,N-di (C1-C6) alkylaminosulfonyl group.

[0043] Substituent Group B comprises (f1) cyano; (f2) (C3-C6) cycloalkyl; (f3) (C1-C6) alkoxy; and (f4) (C1-C6) alkylthio,

[0044] Substituent group C comprises (g1) cyano; (g2) (C1-C6) alkyl; (g13) halogenated (C1-C6) alkyl; (g15) (C2-C6) alkynyl; and (g16) phenyl,

[0045] The substituent group D includes (h1) a halogen atom; (h2) a cyano group; (h3) a hydroxyl group; (h5) a (C1-C6) alkyl group; (h6) a (C1-C6) alkoxy group; (h8) a (C1-C6) alkylthio group; (h11) a halo (C1-C6) alkyl group; (h12) a halo (C1-C6) alkoxy group; (h17) a (C1-C6) alkoxycarbonyl group; (h20) a methylenedioxy group formed by two adjacent substituents, optionally substituted with one or two substituents selected from a halogen atom, a phenyl group and a (C1-C6) alkyl group; and (h21) a nitro group.

[0046] [5] An insecticide comprising the compound or its salt or N-oxide according to any one of [1] to [4] as an active ingredient.

[0047] [6] An agricultural and horticultural insecticide comprising the compound or its salt or N-oxide according to any one of [1] to [4] as an active ingredient.

[0048] [7] An external parasite control agent for animals, comprising the compound or its salt or N-oxide according to any one of [1] to [4] as an active ingredient.

[0049] [8] An internal parasite control agent for animals, comprising the compound or its salt or N-oxide according to any one of [1] to [4] as an active ingredient.

[0050] [9] A method for using an insecticide, wherein:

[0051] Treat plants or soil with an effective amount of the pesticide described in [5] or [6].

[0052]

[10] Use of the compound according to any one of [1] to [4] or its salt or N-oxide as an insecticide.

[0053]

[11] A compound represented by the general formula (13A) and a salt thereof,

[0054] General formula (13A)

[0055] [Chemical formula 2]

[0056]

[0057] {In the formula, R 1 represents (a1) a hydrogen atom; (a2) a (C1-C6) alkyl group; (a3) ​​a (C2-C6) alkenyl group; (a4) a (C2-C6) alkynyl group; (a5) a (C3-C6) cycloalkyl group; (a6) a (C1-C6) alkoxy group; (a7) a halogenated (C1-C6) alkyl group; (a8) a (C1-C6) alkylcarbonyl group; (a9) a (C1-C6) alkoxycarbonyl group; (a10) a alkyl group having a cyano group, a (C1-C6) alkoxy group and a (C3-C6) alkoxy group on the chain, respectively. (a11) substituted (C1-C6)alkyl having 1 to 3 substituents in the (C1-C6)cycloalkyl group; (a12) substituted thiazolylmethyl having 1 or 2 substituents on the ring independently selected from halogen atoms, (C1-C6)alkyl groups and (C1-C6)alkoxy groups; (a13) benzyl; or (a14) substituted benzyl having 1 to 3 substituents on the ring independently selected from halogen atoms, (C1-C6)alkyl groups and (C1-C6)alkoxy groups.

[0058] R 2 represents (b1) an aryl group; (b2) a substituted aryl group having one or more substituents independently selected from the substituent group A on the ring; (b3) a 5- to 10-membered heterocyclic group; or (b4) a substituted 5- to 10-membered heterocyclic group having one or more substituents independently selected from the substituent group A on the ring.

[0059] Among them, R 2In the tetrahydropyridazine ring, the atoms adjacent to the atoms bonded to the tetrahydropyridazine ring are unsubstituted (C1-C6) alkylsulfonyl, halogenated (C1-C6) alkylsulfonyl, N-(C1-C6) alkylaminosulfonyl, N,N-di(C1-C6) alkylaminosulfonyl and R 6 -(R 7 -N=)O=S group (where R 6 represents (C1-C6)alkyl, (C3-C6)cycloalkyl, halogenated (C1-C6)alkyl or (C1-C6)alkoxy (C1-C6)alkyl, R 7 represents a hydrogen atom, a cyano group, a (C1-C6)alkyl group, a (C3-C6)cycloalkyl group, a halogenated (C1-C6)alkyl group, a (C2-C6)alkylcarbonyl group or a halogenated (C2-C6)alkylcarbonyl group),

[0060] Substituent group A includes (e1) a halogen atom; (e2) a cyano group; (e3) a nitro group; (e4) a hydroxyl group; (e5) a carboxyl group; (e6) a (C1-C6) alkyl group; (e7) a (C2-C6) alkenyl group; (e8) a (C2-C6) alkynyl group; (e9) a (C1-C6) alkoxy group; (e10) a (C3-C6) cycloalkyl group; (e11) a (C1-C6) alkylthio group; (e12) a (C1-C6) alkylsulfinyl group; (e13) a (C1-C6) alkylsulfonyl group; (e14) a halogenated (C1-C6) alkyl group; ( e15) halo (C2-C6) alkenyl; (e16) halo (C2-C6) alkynyl; (e17) halo (C1-C6) alkoxy; (e18) halo (C3-C6) cycloalkyl; (e19) halo (C1-C6) alkylthio; (e20) halo (C1-C6) alkylsulfinyl; (e21) halo (C1-C6) alkylsulfonyl; (e22) (C1-C6) alkylcarbonylamino; (e23) halo (C1-C6) alkylcarbonylamino; (e24) (C1-C6) alkylsulfonylamino; (e25) halo (C1-C6) alkylsulfonylamino; (e26) SF5 group; (e27) (C1-C6) alkoxy (C1-C6) alkyl; (e28) N-(C1-C6) alkylcarboxamide; (e29) N-halo (C1-C6) alkylcarboxamide; (e30) oxadiazolyl; (e31) having on the ring independently selected from halogen atoms, cyano, (C1-C6) alkyl, (C1-C6) alkoxy, (C3-C6) cycloalkyl, (C1-C6) alkylthio, (C1-C6) alkylthio substituted oxadiazolyl with one substituent selected from sulfonyl, (C1-C6)alkylsulfonyl, halo(C1-C6)alkyl and halo(C1-C6)alkoxy; (e32) (C1-C6)alkoxycarbonyl; (e33) methylenedioxy optionally substituted with one or two substituents selected from halogen atoms, phenyl and (C1-C6)alkyl, formed by two adjacent substituents; (e34) N-(C1-C6)alkylaminosulfonyl; (e35) N,N-di(C1-C6)alkylaminosulfonyl; (e36) R 6 -(R 7 -N=)O=S group (where R 6 represents (C1-C6)alkyl, (C3-C6)cycloalkyl, halogenated (C1-C6)alkyl or (C1-C6)alkoxy (C1-C6)alkyl, R 7represents a hydrogen atom, a cyano group, a (C1-C6) alkyl group, a (C3-C6) cycloalkyl group, a halogenated (C1-C6) alkyl group, a (C2-C6) alkylcarbonyl group or a halogenated (C2-C6) alkylcarbonyl group); and (e37) a substituted (C3-C6) cycloalkyl group having 1 to 3 substituents independently selected from a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group and a (C1-C6) alkylcarbonyl group on the ring.}

[0061]

[12] The compound and salt thereof according to

[11] , wherein

[0062] R 1 and substituent group A is the same as

[11] ,

[0063] R 2(b5) phenyl; (b6) substituted phenyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b7) pyridyl; (b8) substituted pyridyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b9) pyridazinyl; (b10) substituted pyridazinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b11) pyrimidinyl; (b12) substituted pyrimidinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b13) pyrazinyl; (b14) substituted pyrazinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b15) furanyl; (b16) (b17) substituted furanyl having 1 to 3 substituents from Substituent Group A; (b18) substituted thienyl having 1 to 3 substituents independently selected from Substituent Group A on the ring; (b19) isoxazolyl; (b20) substituted isoxazolyl having 1 to 2 substituents independently selected from Substituent Group A on the ring; (b21) oxazolyl; (b22) substituted oxazolyl having 1 to 2 substituents independently selected from Substituent Group A on the ring; (b23) pyrazolyl; (b24) substituted pyrazolyl having 1 to 3 substituents independently selected from Substituent Group A on the ring; (b25) imidazolyl; (b26) substituted imidazole having 1 to 3 substituents independently selected from Substituent Group A on the ring (b27) triazolyl; (b28) substituted triazolyl having 1 to 2 substituents independently selected from the substituent group A on the ring; (b29) thiazolyl; (b30) substituted thiazolyl having 1 to 2 substituents independently selected from the substituent group A on the ring; (b31) isothiazolyl; (b32) substituted isothiazolyl having 1 to 2 substituents independently selected from the substituent group A on the ring; (b33) thiadiazolyl; (b34) substituted thiadiazolyl having 1 substituent independently selected from the substituent group A on the ring; (b35) imidazopyridinyl; (b36) substituted imidazopyridinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b37) quinoxalinyl ; (b38) substituted quinoxalinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b39) benzoxazolyl; (b40) substituted benzoxazolyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b41) benzimidazolyl; (b42) substituted benzimidazolyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b43) benzothiazolyl; (b44) substituted benzothiazolyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b45) thiazolopyridinyl; (b46) substituted thiazolopyridinyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b47) quinolyl;(b48) substituted quinolyl having 1 to 6 substituents independently selected from the substituent group A on the ring; (b49) naphthyl; (b50) substituted naphthyl having 1 to 7 substituents independently selected from the substituent group A on the ring; (b51) triazine; (b52) substituted triazine having 1 to 2 substituents independently selected from the substituent group A on the ring; (b53) pyrrolyl; (b54) substituted pyrrolyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b55) tetrazolyl; (b56) substituted tetrazolyl having 1 substituent independently selected from the substituent group A on the ring; (b57) oxadiazolyl; (b58) 1 substituent independently selected from the substituent group A on the ring (b59) 2-oxopyridyl; (b60) substituted 2-oxopyridyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b61) benzofuranyl; (b62) substituted benzofuranyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b63) benzisoxazolyl; (b64) substituted benzisoxazolyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b65) benzothienyl; (b66) substituted benzothienyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b67) benzisothiazolyl; (b68) substituted 1 to 4 substituents independently selected from the substituent group A on the ring (b69) indolyl; (b70) substituted indolyl having 1 to 6 substituents independently selected from substituent group A on the ring; (b71) isoindolyl; (b72) substituted isoindolyl having 1 to 6 substituents independently selected from substituent group A on the ring; (b73) indazolyl; (b74) substituted indazolyl having 1 to 5 substituents independently selected from substituent group A on the ring; (b75) benzotriazolyl; (b76) substituted benzotriazolyl having 1 to 4 substituents independently selected from substituent group A on the ring; (b77) furanopyridinyl; (b78) substituted furanopyridinyl having 1 to 4 substituents independently selected from substituent group A on the ring; b79) thienopyridinyl; (b80) substituted thienopyridinyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b81) indolizinyl; (b82) substituted indolizinyl having 1 to 6 substituents independently selected from the substituent group A on the ring; (b83) pyrrolopyridinyl; (b84) substituted pyrrolopyridinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b85) pyrrolopyrimidinyl; (b86) substituted pyrrolopyrimidinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b87) oxazolopyridinyl; (b88) substituted oxazolopyridinyl having 1 to 3 substituents independently selected from the substituent group A on the ring;(b89) isoxazolopyridinyl; (b90) substituted isoxazolopyridinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b91) isothiazolopyridinyl; (b92) substituted isothiazolopyridinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b93) imidazopyrimidinyl; (b94) substituted imidazopyrimidinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b95) pyrazolopyridinyl; (b96) substituted pyrazolopyridinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b97) pyrazolopyrimidinyl; (b98) substituted pyrazolopyrimidinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b99) triazolopyridinyl; (b100) substituted pyrazolopyridinyl having 1 to 4 substituents independently selected from the substituent group A on the ring Substituted triazolopyridinyl; (b101) triazolopyrimidinyl; (b102) substituted triazolopyrimidinyl having 1 to 4 substituents independently selected from substituent group A on the ring; (b103) isoquinolyl; (b104) substituted isoquinolyl having 1 to 6 substituents independently selected from substituent group A on the ring; (b105) oxazinyl; (b106) substituted triazolopyrimidinyl having 1 to 5 substituents independently selected from substituent group A on the ring substituted oxazinyl; (b107) phthalazinyl; (b108) substituted phthalazinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b109) quinazolinyl; (b110) substituted quinazolinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b111) naphthyridinyl; or (b112) substituted naphthyridinyl having 1 to 5 substituents independently selected from the substituent group A on the ring. ;

[0064]

[13] The compound and salt thereof according to

[11] or

[12] , wherein

[0065] R 1 is (a1) a hydrogen atom; (a2) a (C1-C6) alkyl group; or (a4) a (C2-C6) alkynyl group,

[0066] R 2(b5) phenyl; (b6) substituted phenyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b7) pyridyl; (b8) substituted pyridyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b9) pyridazinyl; (b10) substituted pyridazinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b11) pyrimidinyl; (b12) substituted pyrimidinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b13) pyrazinyl; (b14) substituted pyrazinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b15) furanyl; (b16) (b17) substituted furanyl having 1 to 3 substituents from Substituent Group A; (b18) substituted thienyl having 1 to 3 substituents independently selected from Substituent Group A on the ring; (b19) isoxazolyl; (b20) substituted isoxazolyl having 1 to 2 substituents independently selected from Substituent Group A on the ring; (b21) oxazolyl; (b22) substituted oxazolyl having 1 to 2 substituents independently selected from Substituent Group A on the ring; (b23) pyrazolyl; (b24) substituted pyrazolyl having 1 to 3 substituents independently selected from Substituent Group A on the ring; (b25) imidazolyl; (b26) substituted imidazole having 1 to 3 substituents independently selected from Substituent Group A on the ring (b27) triazolyl; (b28) substituted triazolyl having 1 to 2 substituents independently selected from the substituent group A on the ring; (b29) thiazolyl; (b30) substituted thiazolyl having 1 to 2 substituents independently selected from the substituent group A on the ring; (b31) isothiazolyl; (b32) substituted isothiazolyl having 1 to 2 substituents independently selected from the substituent group A on the ring; (b33) thiadiazolyl; (b34) substituted thiadiazolyl having 1 substituent independently selected from the substituent group A on the ring; (b35) imidazopyridinyl; (b36) substituted imidazopyridinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b37) quinoxalinyl ; (b38) substituted quinoxalinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b39) benzoxazolyl; (b40) substituted benzoxazolyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b41) benzimidazolyl; (b42) substituted benzimidazolyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b43) benzothiazolyl; (b44) substituted benzothiazolyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b45) thiazolopyridinyl; (b46) substituted thiazolopyridinyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b47) quinolyl;or (b48) a substituted quinolyl group having 1 to 6 substituents independently selected from Substituent Group A on the ring;

[0067] Substituent group A includes (e1) a halogen atom; (e2) a cyano group; (e4) a hydroxyl group; (e5) a carboxyl group; (e6) a (C1-C6) alkyl group; (e9) a (C1-C6) alkoxy group; (e10) a (C3-C6) cycloalkyl group; (e11) a (C1-C6) alkylthio group; (e12) a (C1-C6) alkylsulfinyl group; (e13) a (C1-C6) alkylsulfonyl group; (e14) a halogenated (C1-C6) alkyl group -C6) alkyl; (e17) halo (C1-C6) alkoxy; (e18) halo (C3-C6) cycloalkyl; (e19) halo (C1-C6) alkylthio; (e20) halo (C1-C6) alkylsulfinyl; (e21) halo (C1-C6) alkylsulfonyl; (e22) (C1-C6) alkylcarbonylamino; (e24) (C1-C6) alkylsulfonylamino; (e28) N-(C1-C6)alkylcarboxamide; (e30)oxadiazolyl; (e31) having on the ring independently selected from halogen atoms, cyano, (C1-C6)alkyl, (C1-C6)alkoxy, (C3-C6)cycloalkyl, (C1-C6)alkylthio, (C1-C6)alkylsulfinyl, (C1-C6)alkylsulfonyl, halo (C1-C6)alkyl and halo (C1-C6)alkoxy (e32) (C1-C6) alkoxycarbonyl; (e33) a methylenedioxy group optionally substituted with one or two substituents selected from halogen atoms, phenyl and (C1-C6) alkyl, formed by two adjacent substituents; (e34) N-(C1-C6) alkylaminosulfonyl; (e35) N,N-di(C1-C6) alkylaminosulfonyl; (e36) R 6 -(R 7 -N=)O=S group (where R 6 represents (C1-C6)alkyl, (C3-C6)cycloalkyl, halogenated (C1-C6)alkyl or (C1-C6)alkoxy (C1-C6)alkyl, R 7 represents a hydrogen atom, a cyano group, a (C1-C6) alkyl group, a (C3-C6) cycloalkyl group, a halogenated (C1-C6) alkyl group, a (C2-C6) alkylcarbonyl group or a halogenated (C2-C6) alkylcarbonyl group); and (e37) a substituted (C3-C6) cycloalkyl group having 1 to 3 substituents on the ring independently selected from a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group and a (C1-C6) alkylcarbonyl group.

[0068]

[14] The compound or salt thereof according to any one of

[11] to

[13] , wherein

[0069] R 1 is (a1) a hydrogen atom,

[0070] R 2 (b5) phenyl; (b6) substituted phenyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b7) pyridyl; (b8) substituted pyridyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b9) pyridazinyl; (b10) substituted pyridazinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b11) pyrimidinyl; (b12) substituted pyrimidinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b13) pyrazinyl; (b14) substituted pyrazinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b23) pyrazolyl; (b24) substituted pyrazolyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b27) triazolyl ; (b28) a substituted triazolyl group having 1 to 2 substituents independently selected from the substituent group A on the ring; (b29) a thiazolyl group; (b30) a substituted thiazolyl group having 1 to 2 substituents independently selected from the substituent group A on the ring; (b33) a thiadiazolyl group; (b34) a substituted thiadiazolyl group having 1 substituent independently selected from the substituent group A on the ring; (b43) a benzothiazolyl group; (b44) a substituted benzothiazolyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b45) a thiazolopyridyl group; (b46) a substituted thiazolopyridyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b47) a quinolyl group; or (b48) a substituted quinolyl group having 1 to 6 substituents independently selected from the substituent group A on the ring,

[0071] Substituent Group A includes (e1) a halogen atom; (e2) a cyano group; (e6) a (C1-C6) alkyl group; (e9) a (C1-C6) alkoxy group; (e11) a (C1-C6) alkylthio group; (e12) a (C1-C6) alkylsulfinyl group; (e13) a (C1-C6) alkylsulfonyl group; (e14) a halo-substituted (C1-C6) alkyl group; (e17) a halo-substituted (C1-C6) alkoxy group; (e19) a halo-substituted (C1-C6) alkylthio group; (e21) a halo-substituted (C1-C6) alkylsulfonyl group; (e32) a (C1-C6) alkoxycarbonyl group; (e34) an N-(C1-C6) alkylaminosulfonyl group; and (e35) an N,N-di(C1-C6) alkylaminosulfonyl group.

[0072]

[15] A compound represented by the general formula (3A) and a salt thereof,

[0073] General formula (3A)

[0074] [Chemical formula 3]

[0075]

[0076] {In the formula, R 1 represents (a1) a hydrogen atom; (a2) a (C1-C6) alkyl group; (a3) ​​a (C2-C6) alkenyl group; (a4) a (C2-C6) alkynyl group; (a5) a (C3-C6) cycloalkyl group; (a6) a (C1-C6) alkoxy group; (a7) a halogenated (C1-C6) alkyl group; (a8) a (C1-C6) alkylcarbonyl group; (a9) a (C1-C6) alkoxycarbonyl group; (a10) a alkyl group having a cyano group, a (C1-C6) alkoxy group and a (C3-C6) alkoxy group on the chain, respectively. (a11) substituted (C1-C6)alkyl having 1 to 3 substituents in the (C1-C6)cycloalkyl group; (a12) substituted thiazolylmethyl having 1 or 2 substituents on the ring independently selected from halogen atoms, (C1-C6)alkyl groups and (C1-C6)alkoxy groups; (a13) benzyl; or (a14) substituted benzyl having 1 to 3 substituents on the ring independently selected from halogen atoms, (C1-C6)alkyl groups and (C1-C6)alkoxy groups.

[0077] R 2 represents (b1) an aryl group; (b2) a substituted aryl group having one or more substituents independently selected from the substituent group A on the ring; (b3) a 5- to 10-membered heterocyclic group; or (b4) a substituted 5- to 10-membered heterocyclic group having one or more substituents independently selected from the substituent group A on the ring.

[0078] Among them, R 2 In the tetrahydropyridazine ring, the atoms adjacent to the atoms bonded to the tetrahydropyridazine ring are unsubstituted (C1-C6) alkylsulfonyl, halogenated (C1-C6) alkylsulfonyl, N-(C1-C6) alkylaminosulfonyl, N,N-di(C1-C6) alkylaminosulfonyl and R 6 -(R 7 -N=)O=S group (where R 6 represents (C1-C6)alkyl, (C3-C6)cycloalkyl, halogenated (C1-C6)alkyl or (C1-C6)alkoxy (C1-C6)alkyl, R 7 represents a hydrogen atom, a cyano group, a (C1-C6)alkyl group, a (C3-C6)cycloalkyl group, a halogenated (C1-C6)alkyl group, a (C2-C6)alkylcarbonyl group or a halogenated (C2-C6)alkylcarbonyl group),

[0079] R 5 represents (i1) (C1-C6) alkyl; or (i2) (C1-C6) alkoxy (C1-C6) alkyl.

[0080] Substituent group A includes (e1) a halogen atom; (e2) a cyano group; (e3) a nitro group; (e4) a hydroxyl group; (e5) a carboxyl group; (e6) a (C1-C6) alkyl group; (e7) a (C2-C6) alkenyl group; (e8) a (C2-C6) alkynyl group; (e9) a (C1-C6) alkoxy group; (e10) a (C3-C6) cycloalkyl group; (e11) a (C1-C6) alkylthio group; (e12) a (C1-C6) alkylsulfinyl group; (e13) a (C1-C6) alkylsulfonyl group; (e14) a halogenated (C1-C6) alkyl group; ( e15) halo (C2-C6) alkenyl; (e16) halo (C2-C6) alkynyl; (e17) halo (C1-C6) alkoxy; (e18) halo (C3-C6) cycloalkyl; (e19) halo (C1-C6) alkylthio; (e20) halo (C1-C6) alkylsulfinyl; (e21) halo (C1-C6) alkylsulfonyl; (e22) (C1-C6) alkylcarbonylamino; (e23) halo (C1-C6) alkylcarbonylamino; (e24) (C1-C6) alkylsulfonylamino; (e25) halo (C1-C6) alkylsulfonylamino; (e26) SF5 group; (e27) (C1-C6) alkoxy (C1-C6) alkyl; (e28) N-(C1-C6) alkylcarboxamide; (e29) N-halo (C1-C6) alkylcarboxamide; (e30) oxadiazolyl; (e31) having on the ring independently selected from halogen atoms, cyano, (C1-C6) alkyl, (C1-C6) alkoxy, (C3-C6) cycloalkyl, (C1-C6) alkylthio, (C1-C6) alkylthio substituted oxadiazolyl with one substituent selected from sulfonyl, (C1-C6)alkylsulfonyl, halo(C1-C6)alkyl and halo(C1-C6)alkoxy; (e32) (C1-C6)alkoxycarbonyl; (e33) methylenedioxy optionally substituted with one or two substituents selected from halogen atoms, phenyl and (C1-C6)alkyl, formed by two adjacent substituents; (e34) N-(C1-C6)alkylaminosulfonyl; (e35) N,N-di(C1-C6)alkylaminosulfonyl; (e36) R 6 -(R 7 -N=)O=S group (where R 6 represents (C1-C6)alkyl, (C3-C6)cycloalkyl, halogenated (C1-C6)alkyl or (C1-C6)alkoxy (C1-C6)alkyl, R 7represents a hydrogen atom, a cyano group, a (C1-C6) alkyl group, a (C3-C6) cycloalkyl group, a halogenated (C1-C6) alkyl group, a (C2-C6) alkylcarbonyl group or a halogenated (C2-C6) alkylcarbonyl group); and (e37) a substituted (C3-C6) cycloalkyl group having 1 to 3 substituents independently selected from a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group and a (C1-C6) alkylcarbonyl group on the ring.}

[0081]

[16] The compound and salt thereof according to

[15] , wherein

[0082] R 1 , R 5 and substituent group A is the same as

[15] ,

[0083] R 2(b5) phenyl; (b6) substituted phenyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b7) pyridyl; (b8) substituted pyridyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b9) pyridazinyl; (b10) substituted pyridazinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b11) pyrimidinyl; (b12) substituted pyrimidinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b13) pyrazinyl; (b14) substituted pyrazinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b15) furanyl; (b16) (b17) substituted furanyl having 1 to 3 substituents from Substituent Group A; (b18) substituted thienyl having 1 to 3 substituents independently selected from Substituent Group A on the ring; (b19) isoxazolyl; (b20) substituted isoxazolyl having 1 to 2 substituents independently selected from Substituent Group A on the ring; (b21) oxazolyl; (b22) substituted oxazolyl having 1 to 2 substituents independently selected from Substituent Group A on the ring; (b23) pyrazolyl; (b24) substituted pyrazolyl having 1 to 3 substituents independently selected from Substituent Group A on the ring; (b25) imidazolyl; (b26) substituted imidazolyl having 1 to 3 substituents independently selected from Substituent Group A on the ring Azolyl; (b27) triazolyl; (b28) substituted triazolyl having 1 to 2 substituents independently selected from the substituent group A on the ring; (b29) thiazolyl; (b30) substituted thiazolyl having 1 to 2 substituents independently selected from the substituent group A on the ring; (b31) isothiazolyl; (b32) substituted isothiazolyl having 1 to 2 substituents independently selected from the substituent group A on the ring; (b33) thiadiazolyl; (b34) substituted thiadiazolyl having 1 substituent independently selected from the substituent group A on the ring; (b35) imidazopyridinyl; (b36) substituted imidazopyridinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b37) quinoxaline (b38) substituted quinoxalinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b39) benzoxazolyl; (b40) substituted benzoxazolyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b41) benzimidazolyl; (b42) substituted benzimidazolyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b43) benzothiazolyl; (b44) substituted benzothiazolyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b45) thiazolopyridinyl; (b46) thiazolopyridinyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b47) quinolyl;(b48) substituted quinolyl having 1 to 6 substituents independently selected from the substituent group A on the ring; (b49) naphthyl; (b50) substituted naphthyl having 1 to 7 substituents independently selected from the substituent group A on the ring; (b51) triazine; (b52) substituted triazine having 1 to 2 substituents independently selected from the substituent group A on the ring; (b53) pyrrolyl; (b54) substituted pyrrolyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b55) tetrazolyl; (b56) substituted tetrazolyl having 1 substituent independently selected from the substituent group A on the ring; (b57) oxadiazolyl; (b58) 1 substituent independently selected from the substituent group A on the ring (b59) 2-oxopyridyl; (b60) substituted 2-oxopyridyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b61) benzofuranyl; (b62) substituted benzofuranyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b63) benzisoxazolyl; (b64) substituted benzisoxazolyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b65) benzothienyl; (b66) substituted benzothienyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b67) benzisothiazolyl; (b68) substituted 1 to 4 substituents independently selected from the substituent group A on the ring (b69) indolyl; (b70) substituted indolyl having 1 to 6 substituents independently selected from substituent group A on the ring; (b71) isoindolyl; (b72) substituted isoindolyl having 1 to 6 substituents independently selected from substituent group A on the ring; (b73) indazolyl; (b74) substituted indazolyl having 1 to 5 substituents independently selected from substituent group A on the ring; (b75) benzotriazolyl; (b76) substituted benzotriazolyl having 1 to 4 substituents independently selected from substituent group A on the ring; (b77) furanopyridinyl; (b78) substituted furanopyridinyl having 1 to 4 substituents independently selected from substituent group A on the ring; b79) thienopyridinyl; (b80) substituted thienopyridinyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b81) indolizinyl; (b82) substituted indolizinyl having 1 to 6 substituents independently selected from the substituent group A on the ring; (b83) pyrrolopyridinyl; (b84) substituted pyrrolopyridinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b85) pyrrolopyrimidinyl; (b86) substituted pyrrolopyrimidinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b87) oxazolopyridinyl; (b88) substituted oxazolopyridinyl having 1 to 3 substituents independently selected from the substituent group A on the ring;(b89) isoxazolopyridinyl; (b90) substituted isoxazolopyridinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b91) isothiazolopyridinyl; (b92) substituted isothiazolopyridinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b93) imidazopyrimidinyl; (b94) substituted imidazopyrimidinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b95) pyrazolopyridinyl; (b96) substituted pyrazolopyridinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b97) pyrazolopyrimidinyl; (b98) substituted pyrazolopyrimidinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b99) triazolopyridinyl; (b100) substituted pyrazolopyridinyl having 1 to 4 substituents independently selected from the substituent group A on the ring Substituted triazolopyridinyl; (b101) triazolopyrimidinyl; (b102) substituted triazolopyrimidinyl having 1 to 4 substituents independently selected from substituent group A on the ring; (b103) isoquinolyl; (b104) substituted isoquinolyl having 1 to 6 substituents independently selected from substituent group A on the ring; (b105) oxazinyl; (b106) substituted triazolopyrimidinyl having 1 to 5 substituents independently selected from substituent group A on the ring substituted oxazinyl; (b107) phthalazinyl; (b108) substituted phthalazinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b109) quinazolinyl; (b110) substituted quinazolinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b111) naphthyridinyl; or (b112) substituted naphthyridinyl having 1 to 5 substituents independently selected from the substituent group A on the ring. ;

[0084]

[17] The compound and salt thereof according to

[15] or

[16] , wherein

[0085] R 1 is (a1) a hydrogen atom; (a2) a (C1-C6) alkyl group; or (a4) a (C2-C6) alkynyl group,

[0086] R 2(b5) phenyl; (b6) substituted phenyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b7) pyridyl; (b8) substituted pyridyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b9) pyridazinyl; (b10) substituted pyridazinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b11) pyrimidinyl; (b12) substituted pyrimidinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b13) pyrazinyl; (b14) substituted pyrazinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b15) furanyl; (b16) (b17) substituted furanyl having 1 to 3 substituents from Substituent Group A; (b18) substituted thienyl having 1 to 3 substituents independently selected from Substituent Group A on the ring; (b19) isoxazolyl; (b20) substituted isoxazolyl having 1 to 2 substituents independently selected from Substituent Group A on the ring; (b21) oxazolyl; (b22) substituted oxazolyl having 1 to 2 substituents independently selected from Substituent Group A on the ring; (b23) pyrazolyl; (b24) substituted pyrazolyl having 1 to 3 substituents independently selected from Substituent Group A on the ring; (b25) imidazolyl; (b26) substituted imidazole having 1 to 3 substituents independently selected from Substituent Group A on the ring (b27) triazolyl; (b28) substituted triazolyl having 1 to 2 substituents independently selected from the substituent group A on the ring; (b29) thiazolyl; (b30) substituted thiazolyl having 1 to 2 substituents independently selected from the substituent group A on the ring; (b31) isothiazolyl; (b32) substituted isothiazolyl having 1 to 2 substituents independently selected from the substituent group A on the ring; (b33) thiadiazolyl; (b34) substituted thiadiazolyl having 1 substituent independently selected from the substituent group A on the ring; (b35) imidazopyridinyl; (b36) substituted imidazopyridinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b37) quinoxalinyl ; (b38) substituted quinoxalinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b39) benzoxazolyl; (b40) substituted benzoxazolyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b41) benzimidazolyl; (b42) substituted benzimidazolyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b43) benzothiazolyl; (b44) substituted benzothiazolyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b45) thiazolopyridinyl; (b46) substituted thiazolopyridinyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b47) quinolyl;or (b48) a substituted quinolyl group having 1 to 6 substituents independently selected from Substituent Group A on the ring;

[0087] R 5 is (i1) (C1-C6) alkyl; or (i2) (C1-C6) alkoxy (C1-C6) alkyl,

[0088] Substituent group A includes (e1) a halogen atom; (e2) a cyano group; (e4) a hydroxyl group; (e5) a carboxyl group; (e6) a (C1-C6) alkyl group; (e9) a (C1-C6) alkoxy group; (e10) a (C3-C6) cycloalkyl group; (e11) a (C1-C6) alkylthio group; (e12) a (C1-C6) alkylsulfinyl group; (e13) a (C1-C6) alkylsulfonyl group; (e14) a halogenated (C1-C6) alkyl group -C6) alkyl; (e17) halo (C1-C6) alkoxy; (e18) halo (C3-C6) cycloalkyl; (e19) halo (C1-C6) alkylthio; (e20) halo (C1-C6) alkylsulfinyl; (e21) halo (C1-C6) alkylsulfonyl; (e22) (C1-C6) alkylcarbonylamino; (e24) (C1-C6) alkylsulfonylamino; (e28) N-(C1-C6)alkylcarboxamide; (e30)oxadiazolyl; (e31) having on the ring independently selected from halogen atoms, cyano, (C1-C6)alkyl, (C1-C6)alkoxy, (C3-C6)cycloalkyl, (C1-C6)alkylthio, (C1-C6)alkylsulfinyl, (C1-C6)alkylsulfonyl, halo (C1-C6)alkyl and halo (C1-C6)alkoxy (e32) (C1-C6) alkoxycarbonyl; (e33) a methylenedioxy group optionally substituted with one or two substituents selected from halogen atoms, phenyl and (C1-C6) alkyl, formed by two adjacent substituents; (e34) N-(C1-C6) alkylaminosulfonyl; (e35) N,N-di(C1-C6) alkylaminosulfonyl; (e36) R 6 -(R 7 -N=)O=S group (where R 6 represents (C1-C6)alkyl, (C3-C6)cycloalkyl, halogenated (C1-C6)alkyl or (C1-C6)alkoxy (C1-C6)alkyl, R 7represents a hydrogen atom, a cyano group, a (C1-C6) alkyl group, a (C3-C6) cycloalkyl group, a halogenated (C1-C6) alkyl group, a (C2-C6) alkylcarbonyl group or a halogenated (C2-C6) alkylcarbonyl group); and (e37) a substituted (C3-C6) cycloalkyl group having 1 to 3 substituents on the ring independently selected from a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group and a (C1-C6) alkylcarbonyl group.

[0089]

[18] The compound or salt thereof according to any one of

[15] to

[17] , wherein

[0090] R 1 is (a1) a hydrogen atom,

[0091] R 2 (b5) phenyl; (b6) substituted phenyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b7) pyridyl; (b8) substituted pyridyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b9) pyridazinyl; (b10) substituted pyridazinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b11) pyrimidinyl; (b12) substituted pyrimidinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b13) pyrazinyl; (b14) substituted pyrazinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b23) pyrazolyl; (b24) substituted pyrazolyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b27) triazolyl ; (b28) a substituted triazolyl group having 1 to 2 substituents independently selected from the substituent group A on the ring; (b29) a thiazolyl group; (b30) a substituted thiazolyl group having 1 to 2 substituents independently selected from the substituent group A on the ring; (b33) a thiadiazolyl group; (b34) a substituted thiadiazolyl group having 1 substituent independently selected from the substituent group A on the ring; (b43) a benzothiazolyl group; (b44) a substituted benzothiazolyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b45) a thiazolopyridyl group; (b46) a substituted thiazolopyridyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b47) a quinolyl group; or (b48) a substituted quinolyl group having 1 to 6 substituents independently selected from the substituent group A on the ring,

[0092] R 5 is (i1)(C1-C6)alkyl,

[0093] Substituent Group A includes (e1) a halogen atom; (e2) a cyano group; (e6) a (C1-C6) alkyl group; (e9) a (C1-C6) alkoxy group; (e11) a (C1-C6) alkylthio group; (e12) a (C1-C6) alkylsulfinyl group; (e13) a (C1-C6) alkylsulfonyl group; (e14) a halo-substituted (C1-C6) alkyl group; (e17) a halo-substituted (C1-C6) alkoxy group; (e19) a halo-substituted (C1-C6) alkylthio group; (e21) a halo-substituted (C1-C6) alkylsulfonyl group; (e32) a (C1-C6) alkoxycarbonyl group; (e34) an N-(C1-C6) alkylaminosulfonyl group; and (e35) an N,N-di(C1-C6) alkylaminosulfonyl group.

[0094] Effects of the Invention

[0095] The compounds of the present invention or their salts have excellent effects as insecticides and are effective not only against pests in the agronomic and horticultural fields but also against pests parasitic on pets such as dogs and cats or livestock such as cattle and sheep. DETAILED DESCRIPTION

[0096] In the definitions of the general formulae (1), (13A) and (3A) of the compounds of the present invention, "halo" means a "halogen atom", which means a chlorine atom, a bromine atom, an iodine atom or a fluorine atom.

[0097] “(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.

[0098] “(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.

[0099] “(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.

[0100] The “(C1-C6)alkylthio group” refers to a linear or branched alkylthio group having 1 to 6 carbon atoms, for example, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, sec-butylthio, tert-butylthio, n-pentylthio, isopentylthio, tert-pentylthio, neopentylthio, 2,3-dimethylpropylthio, 1-ethylpropylthio, 1-methylbutylthio, n-hexylthio, isohexylthio, 1,1,2-trimethylpropylthio, and the like.

[0101] 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.

[0102] 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.

[0103] The "(C1-C6)alkylcarbonyl group" refers to an alkylcarbonyl group having the (C1-C6)alkyl group, such as acetyl, propionyl, butyryl, 2-methylpropionyl, pentanoyl, 2-methylbutyryl, 3-methylbutyryl, pivaloyl, hexanoyl, etc., and an alkylcarbonyl group having 2 to 7 carbon atoms.

[0104] The “(C1-C6)alkylcarbonylamino” refers to an alkylcarbonylamino group having the (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.

[0105] 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.

[0106] “N-(C1-C6)alkylcarboxamide” refers to a linear or branched alkylcarboxamide having 2 to 7 carbon atoms and an alkyl group having 1 to 6 carbon atoms, such as N-methylcarboxamide, N-ethylcarboxamide, N-n-propylcarboxamide, N-isopropylcarboxamide, N-n-butylcarboxamide, N-isobutylcarboxamide, N-sec-butylcarboxamide, N-tert-butylcarboxamide, N-n-pentylcarboxamide, N-isopentylcarboxamide, N-tert-pentylcarboxamide, N-neopentylcarboxamide, N-n-hexylcarboxamide, and N-isohexylcarboxamide.

[0107] 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.

[0108] The “N-(C1-C6)alkylaminosulfonyl group” refers to, for example, N-methylaminosulfonyl, N-ethylaminosulfonyl, N-n-propylaminosulfonyl, N-isopropylaminosulfonyl, N-n-butylaminosulfonyl, N-isobutylaminosulfonyl, 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, The invention also includes N-alkylaminosulfonyl groups having 1 to 6 carbon atoms, such as N-(1-methylbutyl)aminosulfonyl, N-(2-methylbutyl)aminosulfonyl, N-n-hexylaminosulfonyl, N-isohexylaminosulfonyl, N-(2-hexyl)aminosulfonyl, N-(3-hexyl)aminosulfonyl, N-(2-methylpentyl)aminosulfonyl, N-(3-methylpentyl)aminosulfonyl, N-(1,1,2-trimethylpropyl)aminosulfonyl and N-(3,3-dimethylbutyl)aminosulfonyl.

[0109] The “N-(C1-C6)alkylaminosulfonyl group” refers to a linear or branched alkylaminosulfonyl group having 1 to 6 carbon atoms, for example, 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.

[0110] 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. The invention also includes a linear or branched dialkylaminosulfonyl group having 1 to 6 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.

[0111] The "(C1-C6) alkyl", "(C2-C6) alkenyl", "(C2-C6) alkynyl", "(C1-C6) alkoxy", "(C1-C6) alkylthio", "(C1-C6) alkylsulfinyl", "(C1-C6) alkylsulfonyl", "(C3-C6) cycloalkyl", "(C1-C6) alkylcarbonylamino", "(C1-C6) alkylsulfonylamino", "N-(C1-C6) alkylcarboxamide" and the like optionally substituted positions may be substituted with 1 or more halogen atoms, and when the number of substituted halogen atoms is more than 2, the halogen atoms may be the same or different.

[0112] They are respectively represented 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", "halo(C3-C6)cycloalkyl", "halo(C1-C6)alkylcarbonylamino", "halo(C1-C6)alkylsulfonylamino", "N-halo(C1-C6)alkylcarboxamide", etc.

[0113] Expressions such as "(C1-C6)", "(C2-C6)", "(C3-C6)" refer to the range of carbon number of various substituents. In addition, for the group to which the substituent is connected, the above definition can be adopted. For example, in the case of "(C1-C6)alkoxy(C1-C6)alkyl", 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.

[0114] The "aryl group" refers to an aromatic hydrocarbon group having 6 to 10 carbon atoms, such as phenyl, 1-naphthyl, and 2-naphthyl.

[0115] Examples of the "5- to 10-membered heterocyclic group" include a 5- or 6-membered monocyclic aromatic heterocyclic group containing 1 to 4 heteroatoms selected from oxygen atoms, sulfur atoms and nitrogen atoms as ring-constituting atoms other than carbon 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, etc. The ring-constituting atoms of the 5- to 10-membered heterocyclic group may be oxidized by an oxo group.

[0116] The “monocyclic aromatic heterocyclic group” means, for example, 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) The “aromatic fused heterocyclic group” means, for example, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, cinnosinyl, 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, 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, thiazolopyridyl), isothiazolo[2,3-a]pyridyl, isoxazolo[4,5-b]pyridyl, isoxazolo[5,4-b]pyridyl), 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.

[0117] The “monocyclic non-aromatic heterocyclic group” includes, for example, oxetanyl, thietanyl, azadino, pyrrolidinyl, pyrrolidin-2-onyl, piperidinyl, morpholinyl, thiomorpholinyl, piperazinyl, hexamethyleneimino, oxazolidinyl, thiazolidinyl, imidazolidinyl, oxazolinyl, thiazolinyl, isoxazolinyl, imidazolinyl, dioxolyl, dioxolanyl, 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-dioxane The term "non-aromatic fused heterocyclic group" refers to, for example, dihydroindole, dihydroisoindole, dihydrobenzofuranyl, dihydrobenzodioxinyl, dihydrobenzodioxepinyl, tetrahydrobenzofuranyl, chromenyl, dihydroquinolinyl, tetrahydroquinolinyl, dihydroisoquinolinyl, tetrahydroisoquinolinyl, dihydrophthalazinyl, and the like.

[0118] Examples of salts of the compounds represented by the general formula (1), (13A) and (3A) 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 ions, potassium ions, calcium ions and trimethylammonium.

[0119] The compounds represented by the general formula (1), (13A) and (3A) of the present invention and their salts may have one or more asymmetric centers in their structural formulas, and may have two or more optical isomers and diastereomers. The present invention includes all optical isomers and mixtures thereof in any proportion. In addition, the compounds represented by the general formula (1), (13A) and (3A) of the present invention and their salts may have 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, the compounds represented by the general formula (1), (13A) and (3A) of the present invention and their salts may have multiple tautomers. The present invention includes all tautomers and mixtures thereof in any proportion.

[0120] Among the compounds represented by the general formulae (1), (13A) and (3A) of the present invention, preferred embodiments are shown below. The compound represented by the general formula (13A) and the compound represented by the general formula (3A) are useful as synthetic intermediates of the compound represented by the general formula (1).

[0121] In the general formula (1), R 1 Preferred is (a1) a hydrogen atom; (a2) a (C1-C6) alkyl group; or (a4) a (C2-C6) alkynyl group, and more preferred is (a1) a hydrogen atom.

[0122] In the general formula (1), R 2, preferably (b5), (b6), (b7), (b8), (b9), (b10), (b11), (b12), (b13), (b14), (b15), (b16), (b17), (b18), (b19), (b20), (b21), (b22), (b23), (b24), (b25), (b26), (b27), (b28), (b29), (b30), (b31), (b32), (b33), (b34), (b35), (b36), (b37), (b38), (b39), (b40), (b41), (b42), (b43 ), (b44), (b45), (b46), (b47), (b48), (b49), (b50), (b51), (b52), (b53), (b54), (b55), (b56), (b57), (b58), (b59), (b60), (b61), (b62), (b63), (b64), (b65), (b66), (b67), (b68), (b69), (b70), (b71), (b72 ), (b73), (b74), (b75), (b76), (b77), (b78), (b79), (b80), (b81), (b8 (b100), (b101), (b102), (b103), (b104), (b105), (b106), (b107), (b108), (b109), (b110), (b111) or (b112), and more preferably (b5), (b6), (b7), (b8), (b9), (b10), (b112), (b113), (b114), (b115), (b116), (b117), (b118), (b119), (b200), (b201), (b202), (b203), (b204), (b205), (b206), (b207), (b208), (b209), (b210), (b211), or (b212), and more preferably (b212), (b213), (b214), (b215), (b216), (b217), (b218), (b219), (b220), (b221 (b0), (b11), (b12), (b13), (b14), (b15), (b16), (b17), (b18), (b19), (b20), (b21), (b22), (b23), (b24), (b25), (b26), (b27), (b28), (b29), (b30), (b31), (b32), (b33), (b34), (b35), (b36), (b37), (b38), (b39), (b40), (b41), (b42), (b43), (b44), (b45), (b46), (b47) or (b48),More preferably, it is a group of (b5), (b6), (b7), (b8), (b9), (b10), (b11), (b12), (b13), (b14), (b23), (b24), (b27), (b28), (b29), (b30), (b33), (b34), (b43), (b44), (b45), (b46), (b47) or (b48).

[0123] In the general formula (1), R 3 Preferred are (c1) a hydrogen atom; or (c2) a (C1-C6) alkyl group.

[0124] In the general formula (1), R 4 , preferably (d1), (d2), (d3), (d4), (d5), (d8), (d9), (d10), (d11), (d12), (d13), (d14), (d15), (d16), (d17), (d18), (d19), (d20), (d21), (d22), (d23), (d24), (d25), (d26), (d27), (d28), (d29), (d30), (d31), (d32), (d33), (d34), (d35), (d36), (d37), (d38), (d39), (d4 0), (d41), (d42), (d43), (d44), (d45), (d46), (d47), (d48), (d49), (d50), (d51), (d52), (d53), (d54), (d55), (d56) or (d57), more preferably (d1), (d2), (d3), (d4), (d5), (d8), (d9), (d12), (d13), (d14), (d15), (d16), (d17), (d18), (d19), (d20), (d21), (d22), (d24), (d25), (d26), (d27), (d28), (d29), (d30), (d31), (d32), (d33), (d34), (d35), (d36), (d37), (d38), (d39), (d40), (d41), (d42), (d43), (d44), (d45), (d46), (d47), (d48), (d49), (d50), (d51), (d5 (D50), (D51), (D52), (D53), (D54), (D55), (D56) or (D57).

[0125] In the general formula (1), X is preferably an oxygen atom.

[0126] In the general formula (1), Y is preferably an oxygen atom.

[0127] In the general formula (1), it is preferred that X is an oxygen atom and Y is a sulfur atom.

[0128] In the general formula (1), it is preferred that X is a sulfur atom and Y is an oxygen atom.

[0129] In the general formula (1), as the substituent group A, preferably, a group comprising (e1), (e2), (e4), (e5), (e6), (e9), (e10), (e11), (e12), (e13), (e14), (e17), (e18), (e19), (e20), (e21), (e22), (e24), (e28), (e30), (e31), (e32), (e33), (e34), (e35), (e36) and (e37) are included, and a group comprising (e1), (e2), (e6), (e9), (e11), (e12), (e13), (e14), (e17), (e19), (e21), (e32), (e34) and (e35) are included.

[0130] In the general formula (1), as the substituent group B, preferably, the groups comprising (f1), (f2), (f3), (f4), (f5), (f6), (f7), (f8), (f9), (f10) and (f11) are included, and the groups comprising (f1), (f2), (f3) and (f4) are more included.

[0131] In the general formula (1), as the substituent group C, preferably, the groups comprising (g1), (g2), (g3), (g4), (g5), (g6), (g7), (g8), (g9), (g10), (g11), (g12), (g13), (g15) and (g16) are included, and the groups comprising (g1), (g2), (g13), (g15) and (g16) are included more preferably.

[0132] In the general formula (1), as the substituent group D, preferably, a group comprising (h1), (h2), (h3), (h4), (h5), (h6), (h7), (h8), (h9), (h10), (h11), (h12), (h13), (h14), (h15), (h16), (h17), (h18), (h20), (h21), (h22) and (h23) is included, and a group comprising (h1), (h2), (h3), (h5), (h6), (h8), (h11), (h12), (h17), (h20) and (h21) is included is more preferred.

[0133] In the general formula (13A), R 1Preferred is (a1) a hydrogen atom; (a2) a (C1-C6) alkyl group; or (a4) a (C2-C6) alkynyl group, and more preferred is (a1) a hydrogen atom.

[0134] In the general formula (13A), R 2, preferably (b5), (b6), (b7), (b8), (b9), (b10), (b11), (b12), (b13), (b14), (b15), (b16), (b17), (b18), (b19), (b20), (b21), (b22), (b23), (b24), (b25), (b26), (b27), (b28), (b29), (b30), (b31), (b32), (b33), (b34), (b35), (b36), (b37), (b38), (b39), (b40), (b41), (b42), (b43 ), (b44), (b45), (b46), (b47), (b48), (b49), (b50), (b51), (b52), (b53), (b54), (b55), (b56), (b57), (b58), (b59), (b60), (b61), (b62), (b63), (b64), (b65), (b66), (b67), (b68), (b69), (b70), (b71), (b72 ), (b73), (b74), (b75), (b76), (b77), (b78), (b79), (b80), (b81), (b8 (b100), (b101), (b102), (b103), (b104), (b105), (b106), (b107), (b108), (b109), (b110), (b111) or (b112), and more preferably (b5), (b6), (b7), (b8), (b9), (b10), (b112), (b113), (b114), (b115), (b116), (b117), (b118), (b119), (b200), (b201), (b202), (b203), (b204), (b205), (b206), (b207), (b208), (b209), (b210), (b211), or (b212), and more preferably (b212), (b213), (b214), (b215), (b216), (b217), (b218), (b219), (b220), (b221 (b0), (b11), (b12), (b13), (b14), (b15), (b16), (b17), (b18), (b19), (b20), (b21), (b22), (b23), (b24), (b25), (b26), (b27), (b28), (b29), (b30), (b31), (b32), (b33), (b34), (b35), (b36), (b37), (b38), (b39), (b40), (b41), (b42), (b43), (b44), (b45), (b46), (b47) or (b48),More preferably, it is a group of (b5), (b6), (b7), (b8), (b9), (b10), (b11), (b12), (b13), (b14), (b23), (b24), (b27), (b28), (b29), (b30), (b33), (b34), (b43), (b44), (b45), (b46), (b47) or (b48).

[0135] In the general formula (13A), as the substituent group A, preferably, the substituent group A includes the groups (e1), (e2), (e4), (e5), (e6), (e9), (e10), (e11), (e12), (e13), (e14), (e17), (e18), (e19), (e20), (e21), (e22), (e24), (e28), (e30), (e31), (e32), (e33), (e34), (e35), (e36) and (e37) described above, and more preferably, the substituent group A includes the groups (e1), (e2), (e6), (e9), (e11), (e12), (e13), (e14), (e17), (e19), (e21), (e32), (e34) and (e35) described above.

[0136] In the general formula (3A), R 1 Preferred is (a1) a hydrogen atom; (a2) a (C1-C6) alkyl group; or (a4) a (C2-C6) alkynyl group, and more preferred is (a1) a hydrogen atom.

[0137] In the general formula (3A), R 2, preferably (b5), (b6), (b7), (b8), (b9), (b10), (b11), (b12), (b13), (b14), (b15), (b16), (b17), (b18), (b19), (b20), (b21), (b22), (b23), (b24), (b25), (b26), (b27), (b28), (b29), (b30), (b31), (b32), (b33), (b34), (b35), (b36), (b37), (b38), (b39), (b40), (b41), (b42), (b43 ), (b44), (b45), (b46), (b47), (b48), (b49), (b50), (b51), (b52), (b53), (b54), (b55), (b56), (b57), (b58), (b59), (b60), (b61), (b62), (b63), (b64), (b65), (b66), (b67), (b68), (b69), (b70), (b71), (b72 ), (b73), (b74), (b75), (b76), (b77), (b78), (b79), (b80), (b81), (b8 (b100), (b101), (b102), (b103), (b104), (b105), (b106), (b107), (b108), (b109), (b110), (b111) or (b112), and more preferably (b5), (b6), (b7), (b8), (b9), (b10), (b112), (b113), (b114), (b115), (b116), (b117), (b118), (b119), (b200), (b201), (b202), (b203), (b204), (b205), (b206), (b207), (b208), (b209), (b210), (b211), or (b212), and more preferably (b212), (b213), (b214), (b215), (b216), (b217), (b218), (b219), (b220), (b221 (b0), (b11), (b12), (b13), (b14), (b15), (b16), (b17), (b18), (b19), (b20), (b21), (b22), (b23), (b24), (b25), (b26), (b27), (b28), (b29), (b30), (b31), (b32), (b33), (b34), (b35), (b36), (b37), (b38), (b39), (b40), (b41), (b42), (b43), (b44), (b45), (b46), (b47) or (b48),More preferably, it is a group of (b5), (b6), (b7), (b8), (b9), (b10), (b11), (b12), (b13), (b14), (b23), (b24), (b27), (b28), (b29), (b30), (b33), (b34), (b43), (b44), (b45), (b46), (b47) or (b48).

[0138] In the general formula (3A), R 5 Preferred is (i1) (C1-C6) alkyl.

[0139] In the general formula (3A), as the substituent group A, preferably, the substituent group A includes the groups (e1), (e2), (e4), (e5), (e6), (e9), (e10), (e11), (e12), (e13), (e14), (e17), (e18), (e19), (e20), (e21), (e22), (e24), (e28), (e30), (e31), (e32), (e33), (e34), (e35), (e36) and (e37) described above, and more preferably, the substituent group A includes the groups (e1), (e2), (e6), (e9), (e11), (e12), (e13), (e14), (e17), (e19), (e21), (e32), (e34) and (e35) described above.

[0140] 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.

[0141] Manufacturing method 1

[0142] [Chemical formula 4]

[0143]

[0144] {In the formula, R 2 , R 3 and R 4 Same as above.}

[0145] The compound represented by the general formula (1a) of the present invention can be produced from the compound represented by the general formula (11) through the following steps [a], [b], [c], [d], [e] and [f].

[0146] Process [a]

[0147] A step of producing a compound represented by the general formula (9) by reacting a compound represented by the general formula (11) with a benzophenone represented by the formula (10).

[0148] Process [b]

[0149] A step of producing a compound represented by the general formula (7) by reacting a compound represented by the general formula (9) with methyl bromoacetate represented by the formula (8).

[0150] Process [c]

[0151] A step of producing a compound represented by the general formula (6) by hydrolyzing a compound represented by the general formula (7).

[0152] Process [d]

[0153] A step of producing a compound represented by the general formula (4) by condensing a compound represented by the general formula (6) and a compound represented by the general formula (5) through an amidation reaction.

[0154] Process[e]

[0155] A step of producing a compound represented by the general formula (3) by subjecting the compound represented by the general formula (4) to a cyclization reaction.

[0156] Process [f]

[0157] A step of producing a compound represented by the general formula (1a) of the present invention by reacting a compound represented by the general formula (3) with a compound represented by the general formula (2).

[0158] Manufacturing method of step [a]

[0159] The compound represented by the general formula (9) can be produced by reacting the compound represented by the general formula (11) with a benzophenone represented by the formula (10) in the presence of an acid and an inert solvent.

[0160] Examples of the acid used in the reaction include carboxylic acids such as formic acid, acetic acid, propionic acid, and trifluoroacetic acid, and sulfonic acids such as methanesulfonic acid, p-toluenesulfonic acid, and trifluoromethanesulfonic acid. The amount used is usually in the range of 1.0-fold to 10-fold mol relative to 1 mol of the compound represented by the general formula (11).

[0161] The inert solvent used in the present reaction may be any solvent that does not significantly inhibit the progress of the present reaction, and examples thereof include 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, 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, and alcohols such as methanol, ethanol, propanol, butanol and 2-propanol. These inert solvents may be used alone or in combination of two or more. The amount thereof to be used may be appropriately selected from the range of 0.1 to 100 L per 1 mol of the compound represented by the general formula (11).

[0162] This reaction is an equimolar reaction, and each compound can be used in an equimolar manner, and an optional compound can be used in excess. The reaction temperature in this reaction is usually carried out within the range of the boiling point of the solvent used from about 0°C, and the reaction time varies according to the reaction scale, reaction temperature, etc., and is not constant, and can usually 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.

[0163] Manufacturing method of step [b]

[0164] The compound represented by the general formula (7) can be produced by reacting the compound represented by the general formula (9) with methyl bromoacetate represented by the formula (8) in the presence of a base and an inert solvent.

[0165] Examples of the base used in the 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, and alkali metal hydrides such as sodium hydride and potassium hydride. The amount used is usually in the range of 1 to 10 times the molar amount of the compound represented by the general formula (9).

[0166] As the inactive solvent used in the reaction, any solvent that does not hinder the progress of the reaction may be used, for example, inactive solvents such as 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, 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., and these inactive solvents may be used alone or in combination of two or more. The amount used may be appropriately selected in the range of 0.1 to 100 L relative to 1 mol of the compound represented by the general formula (9).

[0167] This reaction is an equimolar reaction, and each compound can be used in an equimolar manner, and an optional compound can be used in excess. The reaction temperature in this reaction is usually carried out within the range of the boiling point of the solvent used from about 0°C, and the reaction time varies according to the reaction scale, reaction temperature, etc., and is not constant, and can usually 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.

[0168] Manufacturing method of step [c]

[0169] The compound represented by the general formula (6) can be produced by reacting the compound represented by the general formula (7) in the presence of concentrated hydrochloric acid and an inert solvent.

[0170] The inert solvent used in the present reaction may be any solvent that does not inhibit the progress of the present reaction, and examples thereof include 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, linear or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, tetrahydrofuran and 2-methyltetrahydrofuran, 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, and water. These inert solvents may be used alone or in combination of two or more. The amount used may be appropriately selected within the range of 0.1 to 100 L per 1 mol of the compound represented by the general formula (7).

[0171] The reaction temperature in this reaction is usually about 0°C and can be carried out within the range of the boiling point of the solvent used. The reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant. It 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 produced by purification by recrystallization, column chromatography, etc. as needed.

[0172] Manufacturing method of step [d]

[0173] The compound represented by the general formula (4) can be produced by condensing the compound represented by the general formula (6) with the monoethyl malonate represented by the formula (5) by an amidation method commonly used in organic synthesis.

[0174] Manufacturing method of step [e]

[0175] The compound represented by the general formula (3) can be produced by subjecting the compound represented by the general formula (4) to a cyclization reaction in the presence of a base and an inert solvent.

[0176] Examples of the base 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 and magnesium carbonate; acetates such as lithium acetate, sodium acetate and potassium acetate; organic bases such as pyridine, picoline, lutidine, triethylamine, tributylamine and diisopropylethylamine; and the amount used is usually in the range of 1 to 10 times the mole of the compound represented by the general formula (4).

[0177] As the inactive solvent used in the reaction, any solvent that does not hinder the progress of the reaction may be used, for example, inactive solvents such as 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, 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 may be used alone or in combination of two or more. The amount used may be appropriately selected in the range of 0.1 to 100 L relative to 1 mol of the compound represented by the general formula (4).

[0178] The reaction temperature in this reaction is usually about 0°C and can be carried out within the range of the boiling point of the solvent used. The reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant. It 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 produced by purification by recrystallization, column chromatography, etc. as needed.

[0179] Manufacturing method of step [f]

[0180] The compound represented by the general formula (1a) of the present invention can be produced by reacting a compound represented by the general formula (3) with a compound represented by the general formula (2) in the presence of an inert solvent.

[0181] The inert solvent used in the present reaction may be any solvent that does not inhibit the progress of the present reaction, and examples thereof include 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, 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, and alcohols such as methanol, ethanol, propanol, butanol and 2-propanol. These inert solvents may be used alone or in combination of two or more. The amount thereof to be used may be appropriately selected within the range of 0.1 to 100 L per 1 mol of the compound represented by the general formula (3).

[0182] This reaction is an equimolar reaction, and each compound can be used in an equimolar manner, and an optional compound can be used in excess. The reaction temperature in this reaction is usually carried out within the range of the boiling point of the solvent used from about 0°C, and the reaction time varies according to the reaction scale, reaction temperature, etc., and is not constant, and can usually 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.

[0183] Manufacturing method 2

[0184] [Chemical formula 5]

[0185]

[0186] {In the formula, R 2 and R 4 Same as above.}

[0187] The compound represented by the general formula (1b-1) of the present invention can be produced from the compound represented by the general formula (3) through the following steps [g] and [h].

[0188] Process [g]

[0189] A step of producing a compound represented by the general formula (13) by decarbonating the compound represented by the general formula (3).

[0190] Process [h]

[0191] A step of producing a compound represented by the general formula (1b-1) of the present invention by reacting a compound represented by the general formula (13) with a compound represented by the general formula (12).

[0192] Manufacturing method of step [g]

[0193] The compound represented by the general formula (13) can be produced by reacting the compound represented by the general formula (3) in the presence of an inert solvent under heating conditions.

[0194] As the inactive solvent used in the reaction, any solvent that does not hinder the progress of the reaction may be used, for example, inactive solvents such as 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, 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, 1,3-dimethyl-2-imidazolidinone, alcohols such as methanol, ethanol, propanol, butanol, and 2-propanol, water, etc. These inactive solvents may be used alone or in combination of two or more. The amount used may be appropriately selected in the range of 0.1 to 100 L relative to 1 mol of the compound represented by the general formula (13).

[0195] The reaction temperature in this reaction is usually about 0°C and can be carried out within the range of the boiling point of the solvent used. The reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant. It 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 produced by purification by recrystallization, column chromatography, etc. as needed.

[0196] Manufacturing method of step [h]

[0197] The compound represented by the general formula (1b-1) of the present invention can be produced by reacting a compound represented by the general formula (13) with a compound represented by the general formula (12) in the presence of a base and an inert solvent.

[0198] 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 diisopropylethylamine. The amount used is usually in the range of 1 to 10 times the mole of the compound represented by the general formula (13).

[0199] As the inactive solvent used in the reaction, any solvent that does not hinder the progress of the reaction may be used, for example, inactive solvents such as 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, 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 may be used alone or in combination of two or more. The amount used may be appropriately selected in the range of 0.1 to 100 L relative to 1 mol of the compound represented by the general formula (13).

[0200] This reaction is an equimolar reaction, and each compound can be used in an equimolar manner, and an optional compound can be used in excess. The reaction temperature in this reaction is usually carried out within the range of the boiling point of the solvent used from about 0°C, and the reaction time varies according to the reaction scale, reaction temperature, etc., and is not constant, and can usually 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.

[0201] Manufacturing method 3

[0202] [Chemical formula 6]

[0203]

[0204] {In the formula, R 2 , R 3 and R 4 Same as above.}

[0205] The compound represented by the general formula (1b-2) of the present invention can be produced from the compound represented by the general formula (1a) through the following step [i].

[0206] Process[i]

[0207] A step of producing a compound represented by the general formula (1b-2) by reacting the compound represented by the general formula (1a) with a sulfiding agent.

[0208] Examples of the sulfurizing agent that can be used in the present reaction include Lawesson's Reagent and phosphorus pentasulfide. The amount of the sulfurizing agent used is usually in the range of 1.0-10 times the mole of the compound represented by the general formula (1a).

[0209] The solvent may or may not be used in the present reaction. The solvent that can be used in the present reaction is any solvent that does not hinder the progress of the present reaction. Examples of the solvent include: 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; 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; and alcohols such as methanol, ethanol, propanol, butanol, and 2-propanol. These inactive solvents may be used alone or in combination of two or more. The amount used may be appropriately selected in the range of 0.1 to 100 L relative to 1 mol of the compound represented by the general formula (1a).

[0210] The reaction temperature in this reaction is usually about 0°C and can be carried out within the range of the boiling point of the solvent used. The reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant. It 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 produced by purification by recrystallization, column chromatography, etc. as needed.

[0211] The salts of the compounds represented by the general formula (1a), (1b-1) or (1b-2) of the present invention are produced by reacting the compounds represented by the general formula (1a), (1b-1) or (1b-2) with an inorganic or organic base in the presence of an inert solvent.

[0212] Examples of the inorganic or organic base used in the 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; carbonates such as lithium carbonate, lithium bicarbonate, sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, calcium carbonate, and magnesium carbonate; acetates such as lithium acetate, sodium acetate, and potassium acetate; and organic bases such as pyridine, picoline, lutidine, triethylamine, tributylamine, and diisopropylethylamine. The amount used is usually in the range of 1 to 10 times the mole of the compound represented by the general formula (1a), (1b-1), or (1b-2).

[0213] As the inactive solvent used in the reaction, any solvent that does not significantly inhibit the progress of the reaction may be used, for example, inactive solvents such as 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, 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, and alcohols such as methanol, ethanol, propanol, butanol, and 2-propanol. These inactive solvents may be used alone or in combination of two or more. The amount used may be appropriately selected in the range of 0.1 to 100 L per mol of the compound represented by the general formula (1a), (1b-1), or (1b-2).

[0214] The reaction temperature in the reaction is usually about 0°C and the boiling point of the solvent used. The reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant. It 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 produced by purification by recrystallization, column chromatography, etc. as needed.

[0215] Manufacturing method of manufacturing intermediate 1

[0216] [Chemical formula 7]

[0217]

[0218] {In the formula, R 2 Same as above.}

[0219] The production intermediate of the compound of the present invention represented by the general formula (11) can be produced from the compound represented by the general formula (14).

[0220] Manufacturing method

[0221] The compound represented by the general formula (11) can be produced by reacting the compound represented by the general formula (14) with sodium nitrite in concentrated hydrochloric acid and then reducing the reaction with a reducing agent.

[0222] Examples of the reducing agent used in the present reaction include sodium sulfite and tin chloride. The amount thereof used is usually appropriately selected within a range of 1.0-fold to 10-fold mol of the compound represented by the general formula (14).

[0223] The reaction temperature in this reaction is usually about 0°C and can be carried out within the range of the boiling point of the solvent used. The reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant. It 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 produced by purification by recrystallization, column chromatography, etc. as needed.

[0224] Intermediate manufacturing method 2

[0225] [Chemical formula 8]

[0226]

[0227] {In the formula, R 2 As above, L represents a leaving group such as a halogen atom, a methanesulfonyl group, a toluenesulfonyl group, or a trifluorosulfonyl group.

[0228] The production intermediate of the compound of the present invention represented by the general formula (11) can be produced from the compound represented by the general formula (15) by the following method.

[0229] Manufacturing method

[0230] The compound represented by the general formula (11) can be produced by reacting the compound represented by the general formula (15) with hydrazine monohydrate in the presence of an inert solvent.

[0231] As the inactive solvent used in this reaction, as long as it does not hinder the progress of this reaction, for example, there can be mentioned: inactive solvents such as chain or cyclic saturated hydrocarbons such as pentane, hexane, cyclohexane, aromatic hydrocarbons such as benzene, toluene, xylene, halogenated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene, chain or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, tetrahydrofuran, alcohols such as methanol, ethanol, propanol, butanol, 2-propanol, etc. These inactive solvents can be used alone or in combination of two or more. The amount used is usually appropriately selected in the range of 0.1 to 100 L relative to 1 mol of the compound represented by general formula (15).

[0232] This reaction is an equimolar reaction, and each compound can be used in an equimolar manner, and an optional compound can be used in excess. The reaction temperature in this reaction is usually carried out within the range of the boiling point of the solvent used from about 0°C, and the reaction time varies according to the reaction scale, reaction temperature, etc., and is not constant, and can usually 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.

[0233] Representative examples of the compound represented by the general formula (1) of the present invention are shown in Tables 1 and 2 below, but the present invention is not limited thereto.

[0234] In the table, "Me" represents methyl, "Et" represents ethyl, "n-Pr" represents n-propyl, "i-Pr" represents isopropyl, "n-Bu" represents n-butyl, "t-Bu" represents tert-butyl, "n-Pen" represents n-pentyl, "c-Pen" represents cyclopentyl, "Ph" represents phenyl, and "Bn" represents benzyl. ● in the structural formula represents the bonding position. Physical properties represent melting point (℃) or H 1 -NMR. H 1 -NMR data are shown in Table 6.

[0235] [Chemical formula 9]

[0236]

[0237] [Table 1]

[0238] Table 1

[0239]

[0240] In Table 1, R in formula (1a) 3 Represents hydrogen atom

[0241] *Sodium salt

[0242] [Table 2]

[0243] Continuation of Table 1

[0244]

[0245] In Table 1, R in formula (1a) 3 Represents hydrogen atom

[0246] [Table 3]

[0247] Continuation of Table 1

[0248]

[0249] In Table 1, R in formula (1a) 3 Represents hydrogen atom

[0250] [Table 4]

[0251] Continuation of Table 1

[0252]

[0253] In Table 1, R in formula (1a) 3 Represents hydrogen atom

[0254] [Table 5]

[0255] Continuation of Table 1

[0256]

[0257] In Table 1, R in formula (1a) 3 Represents hydrogen atom

[0258] [Table 6]

[0259] Continuation of Table 1

[0260]

[0261] In Table 1, R in formula (1a) 3 Represents hydrogen atom

[0262] [Table 7]

[0263] Continuation of Table 1

[0264]

[0265] In Table 1, R in formula (1a) 3 Represents hydrogen atom

[0266] [Table 8]

[0267] Continuation of Table 1

[0268]

[0269] In Table 1, R in formula (1a) 3 Represents hydrogen atom

[0270] [Table 9]

[0271] Continuation of Table 1

[0272]

[0273] In Table 1, R in formula (1a) 3 Represents hydrogen atom

[0274] *Sodium salt

[0275] [Table 10]

[0276] Continuation of Table 1

[0277]

[0278] In Table 1, R in formula (1a) 3 Represents hydrogen atom

[0279] [Table 11]

[0280] Continuation of Table 1

[0281]

[0282] In Table 1, R in formula (1a) 3 Represents hydrogen atom

[0283] [Table 12]

[0284] Continuation of Table 1

[0285]

[0286] In Table 1, R in formula (1a) 3 Represents hydrogen atom

[0287] [Table 13]

[0288] Continuation of Table 1

[0289]

[0290] In Table 1, R in formula (1a) 3 Represents hydrogen atom

[0291] [Table 14]

[0292] Continuation of Table 1

[0293]

[0294] In Table 1, R in formula (1a) 3 Represents hydrogen atom

[0295] [Table 15]

[0296] Continuation of Table 1

[0297]

[0298] In Table 1, R in formula (1a) 3 Represents hydrogen atom

[0299] [Table 16]

[0300] Continuation of Table 1

[0301]

[0302] In Table 1, R in formula (1a) 3 Represents hydrogen atom

[0303] [Table 17]

[0304] Continuation of Table 1

[0305]

[0306] In Table 1, R in formula (1a) 3 Represents hydrogen atom

[0307] [Table 18]

[0308] Continuation of Table 1

[0309]

[0310] In Table 1, R in formula (1a) 3 Represents hydrogen atom

[0311] [Table 19]

[0312] Continuation of Table 1

[0313]

[0314] In Table 1, R in formula (1a) 3 Represents hydrogen atom

[0315] [Table 20]

[0316] Continuation of Table 1

[0317]

[0318] In Table 1, R in formula (1a) 3 Represents hydrogen atom

[0319] [Table 21]

[0320] Continuation of Table 1

[0321]

[0322] In Table 1, R in formula (1a) 3 Represents hydrogen atom

[0323] [Table 22]

[0324] Continuation of Table 1

[0325]

[0326] In Table 1, R in formula (1a) 3 Represents hydrogen atom

[0327] [Table 23]

[0328] Continuation of Table 1

[0329]

[0330] In Table 1, R in formula (1a) 3 Represents hydrogen atom

[0331] [Table 24]

[0332] Continuation of Table 1

[0333]

[0334] In Table 1, R in formula (1a) 3 Represents hydrogen atom

[0335] [Table 25]

[0336] Continuation of Table 1

[0337]

[0338] In Table 1, R in formula (1a) 3 Represents hydrogen atom

[0339] [Table 26]

[0340] Continuation of Table 1

[0341]

[0342] [Chemical formula 10]

[0343]

[0344] [Table 27]

[0345] Table 2

[0346]

[0347] [Table 28]

[0348] Table 2 continued

[0349]

[0350] [Table 29]

[0351] Table 2 continued

[0352]

[0353] [Chemical formula 11]

[0354]

[0355] [Table 30]

[0356] Table 3

[0357]

[0358] [Chemical formula 12]

[0359]

[0360] [Table 31]

[0361] Table 4

[0362]

[0363] [Table 32]

[0364] Table 4 continued

[0365]

[0366] [Table 33]

[0367] Table 4 continued

[0368]

[0369] [Chemical formula 13]

[0370]

[0371] [Table 34]

[0372] Table 5

[0373]

[0374] [Table 35]

[0375] Table 5 continued

[0376]

[0377] [Table 36]

[0378] Table 5 continued

[0379]

[0380] [Table 37]

[0381] Table 5 continued

[0382]

[0383] [Table 38]

[0384] Table 5 continued

[0385]

[0386] [Table 39]

[0387] Table 5 continued

[0388]

[0389] [Table 40]

[0390] Table 6

[0391]

[0392] [Table 41]

[0393] Table 6 continued

[0394]

[0395] [Table 42]

[0396] Table 6 continued

[0397]

[0398] [Table 43]

[0399] Table 6 continued

[0400]

[0401] The agronomic and horticultural insecticide containing the compound represented by the general formula (1) of the present invention or its salt as an active ingredient is suitable for controlling various agricultural, forestry, horticultural, stored-grain pests, sanitary pests or nematodes and other pests that harm rice, fruit trees, vegetables, other crops and flowers.

[0402] Examples of the pests or nematodes include the following.

[0403] 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, Parnaraguttata, Marasmia exigua, Sesamia inferens, Brachmia triannulella, Monema flavescens, Trichoplusia ni), Pleuroptya ruralis, Cystidia couaggaria, Lampides boeticus, Cephonodes hylas, Helicoverpa armigera, Phalerodonta manleyi, Eumeta japonica, Pieris brassicae, Malacosoma neustria testacea, Stathmopoda masinissa, Cuphodes diospyrosella, Archips xylosteanus, Agrotissegetum, Tetramoera schistaceana, Papilio machaonhippocrates, Endoclyta sinensis, Lyonetia prunifoliella), Phyllonorycter ringoneella, Cydia kurokoi, Eucoenogenes aestuosa, Lobesiabotrana), Latoiasinica, Euzophera batangensis, Phalonidia mesotypa, Spilosoma imparilis, Glyphodes pyloalis, Olethreutes mori, Tineola bisselliella, Endoclyta excrescens, Nemapogon granellus, Synanthedon hector, Cydiapomonella, Plutella xylostella, Cnaphalocrocismedinalis, Sesamia calamistis, Scirpophaga incertulas, Pediasia teterrellus), Potato tuber moth (Phthorimaea operculella), Apple ant moth (Stauropus fagi persimilis), Bean pod borer (Etiella zinckenella), Beet armyworm (Spodopteraexigua), White-spotted bat moth (Palpifer sexnotata), Gray-winged armyworm (Spodoptera mauritia), Rice white borer (Scirpophaga innotata), Eight-character cutworm (Xestia c-nigrum), Light-sword greedy armyworm (Spodopteradepravata), Mediterranean moth (Ephestia kuehniella), Plum ruler moth (Angerona prunaria), Moon fan moth (Clostera anastomosis), Soybean armyworm (Pseudoplusia includens), Matsumuraeses falcana, Tobacco armyworm (Helicoverpa assulta), Black-spotted cutworm (Autographanigrisigna), Small cutworm (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, Aedia leucomelas, Narosoideus flavidorsalis, Viminia rumicis, Bucculatrix pyrivorella, Grapholita molesta, Spulerina astaurota, Ectomyelois pyrivorella, Chilo suppressalis, Acrolepiopsis sapporensis), Plodia interpunctella, Hellula undalis, Sitotroga cerealella, Spodoptera litura, Eucosma aporema, Acleriscomariana, Scopelodes contractus, Orgyia thyellina, Spodoptera frugiperda, Ostrinia zaguliaevi, Narangaaenescens, Andraca bipunctata, Paranthrene regalis, Acosmeryx castanea, Phyllocnistis toparcha, Endopiza viteana, Eupoecillia ambiguella), soybean armyworm (Anticarsiagemmatalis), tobacco moth (Cnephasia cinereipalpana), gypsy moth (Lymantria dispar), red pine caterpillar (Dendrolimusspectabilis), Leguminivora glycinivorella, Maruca testulalis, Matsumuraeses phaseoli, Caloptilia soyella, Phyllocnistis citrella, Omiodesindicate, Archips fuscocupreanus, Acanthoplusia agnata, Bambalina sp., Carposina niponensis, Conogethes punctiferalis, Synanthedon sp., Lyonetia clerkella, Papilio helenus, Colias erate poliographus, Phaleraflavescens, Pieris spp. rapae crucivora), Pieris rapae, Euproctis similis, Acrolepiopsis suzukiella, Ostrinia nubilalis, Mamestra brassicae, Ascotisselenaria, Phtheochroides clandestina, Hoshinoaadumbratana, Odonestis pruni japonensis, Triaena intermedia, Adoxophyes orana fasciata, Grapholita inopinata, Spilonota ocellana, Spilonota lechriaspis, Illiberispruni, Argyresthia conjugella, Caloptilia zachrysa), Archipsbreviplicanus, Anomis flava, Pectinophoragossypiella), cotton leaf folder (Notarcha derogata), melon silk borer (Diaphania indica), tobacco budworm (Heliothis virescens) and golden dot borer (Earias cupreoviridis).

[0404] Examples of Hemiptera pests include Nezara antennata, Stenotus rubrovittatus, Graphosoma rubrolineatum, Trigonotylus coelestialium, Aeschynteles maculatus, Creontiadespallidifer, Dysdercus cingulatus, Chrysom phalus ficus, Aonidiella aurantii, Graptopsaltria nigrofuscata, Blissus leucopterus, Icerya purchasi, Piezodorus hybneri, Lagynotomus spp. elongatus), white-winged leafhopper (Thaia subrufa), black rice bug (Scotinopharalurida), rose aphid (Sitobion ibarae), Stariodes iwasakii, coconut round shield scale (Aspidiotusdestructor), pale Thai blind bug (Taylorilygus pallidulus), apricot tumor aphid (Myzusmu mecola), plum white scale (Pseudaulacaspis prunicola), pea aphid (Acyrthosiphon pisum), stink bug (Anacanthocoris striicornis), jumping blind bug (Ectometopterus micantulus), Japanese two-star stink bug (Eysarcoris lewisi), giant leaf foot bug (Molipteryx fuliginosa), large green leafhopper (Cicadellaviridis), red-bellied constriction aphid (Rhopalosophum rufiabdominalis), Saissetia oleate, Trialeurodes vaporariorum, Aguriahana quercus, Lygus spp., Euceraphis punctipennis, Andaspis kashicola, Coccus pseudomagnoliarum, Caveleriussaccharivorus), Galeatus spinifrons, Macrosiphoniella sanborni, Aonidiella citrina, Halyomorpha mista, Stephanitis fasciicarina, Trioza camphorae, Leptocorisa chinensis, Trioza quercicola, Uhlerites latius, Erythroneuracomes, Paromius exiguus, Duplaspidiotus claviger, Nephotettix nigropictus, Halticiellus insularis, Perkinsiella saccharicida, Psylla malivorella), Anomomeura mori, Pseudococcus longispinis, Pseudaulacaspis pentagona, Pulvinaria kuwacola, Apolygus lucorum, Togo hemipterus, Toxoptera aurantii, Saccharicoccus sacchari, Geoica lucifuga, Numata muiri, Comstockaspis perniciosa, Unaspis citri, Aulacorthum solani, Eysarcoris ventralis, Bemisia argentifolii, Cicadellella spectra), Aspidiotusshederae, Liorhyssus hyalinus, Calophya nigridorsalis, Sogatella furcifera, Megoura crassicauda, ​​Brevicoryne brassicae, Aphisglycines), Leptocorisa oratorius, Nephotettix virescens, Uroeucon formosanum, Cyrtopeltistennuis, Bemisia tabaci, Lecanium persicae, Parlatoria theae, Pseudaonidia paeoniae, Empoasca onukii, Plautiastali, Dysaphis tulipae, Macrosiphum euphorbiae, Stephanitis pyrioides, Ceroplastes ceriferus, Parlatoria camelliae, Apolygus spinolai, Nephotettix virescens, Uroeucon formosanum, Cyrtopeltistennuis, Bemisia tabaci, Lecanium persicae, Parlatoria theae, Pseudaonidia paeoniae, Empoasca onukii, Plautiastali, Dysaphis tulipae, Macrosiphum euphorbiae, Stephanitis pyrioides, Ceroplastes ceriferus, Parlatoria camelliae, Apolygus spinolai, Nephotettix virescens, cincticeps), Glaucias subpunctatus, Orthotylus flavosparsus, Rhopalosiphum maidis, Peregrinus maidis, Eysarcorisparvus, Cimex lectularius, Psylla abieti, Nilaparvata lugens, Psylla tobirae, Eurydema rugosum, Schizaphispiricola, Psylla pyricola, Parlatoreopsis pyri, Stephanitis nashi, Dysmicoccus wistariae, Lepholeucaspis japonica, Sappaphis piri, Lipaphis erysimi), Neotoxoptera formosana, Rhopalosophum nymphaeae, Edwardsianarosae, Pinnaspisaspidistrae, Psyllaalni), Speusotettix subfusculus, Alnetoidia alneti, Sogatella panicicola, Adelphocoris lineolatus, Dysdercus poecilus, Parlatoria ziziphi, Uhlerites debile, Laodelphaxstriatellus, Eurydema pulchrum, Cletus trigonus, Cloviapunctata, Empoasca sp., Coccus hesperidum, Pachybrachius luridus, Planococcus kraunhiae, Stenotusbinotatus, Arboridia apicalis, Macrosteles fascifrons, Dolycorisbaccarum, Adelphocoris triannulatus, Viteusvitifolii, Acanthocoris sordidus, Leptocorisa acuta, Macropes obnubilus, Cletus punctiger, Riptortusclavatus, Paratrioza cockerelli, Aphrophora costalis, Lygusdisponsi, Lygus saundersi, Crisicoccus pini, Empoasca abietis, Crisicoccus matsumotoi, Aphis craccivora, Megacopta punctatissimum), Eysarcoris guttiger, Lepidosaphes beckii, Diaphorina citri, Toxoptera citricidus, Planococcus citri, Dialeurodes citruscitri), Aleurocanthus spiniferus, Pseudococcus citriculus, Zyginella citri, Pulvinaria citricola, Coccus discrepans, Pseudaonidia duplex, Pulvinaria aurantii, Lecanium corni, Nezara viridula, Stenodema calcaratum, Rhopalosiphum padi, Sitobion akebiae, Schizaphis graminum, Sorhoanus tritici, Brachycaudus helichrysi, Carpocoris purpureipennis, Myzus persicae, persicae), Hyalopteruspruni, Aphis farinose yanagicola, Metasalis populi, Unaspis yanonensis, Mesohomotoma camphorae, Aphis spiraecola, Aphis pomi, Lepidosaphes ulmi, Psylla mali, Heterocordylusflavipes, Myzus malisuctus, Aphidonuguis mali, Orientus ishidai, Ovatusmalicolens, Eriosoma lanigerum, Ceroplastes rubens and Aphis gossypii, etc.

[0405] 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, and many more. virgifera), Involvulus cupreus, Aulacophora femoralis, Bruchus pisorum, Epilachnavigintioctomaculata, Carpophilus dimidiatus, Cassidanebulosa, Luperomorpha tunebrosa, Phyllotretastriolata, Psacothea hilaris, Aeolesthes chrysothrix, Curculio sikkimensis, Carpophilus hemipterus, Oxycetonia jucunda, Diabrotica spp.), Mimelasplendens, Sitophilus zeamais, Tribolium castaneum, Sitophilus oryzae, Palorus subdepressus, Melolontha japonica, Anoplophoramalasiaca, Neatus picipes, Leptinotarsa ​​decemlineata, Diabrotica undecimpunctata howardi, Sphenophorus venatus, Crioceris quatuor decimpunctata, Conotrachelus nenuphar, Ceuthorhynchidius albosuturalis, Phaedonbrassicae, Lasioderma serricorne, Sitona japonicus, Adoretus tenuimaculatus, Tenebrio molitor, Basilepta balyi, Hypera nigrirostris, Chaetocnema concinna, Anomala cuprea, Heptophyllapicea, Epilachna vigintioctopunctata, Diabroticalongicornis, Eucetonia pilifera, Agriotes spp.), Attagenus unicolor japonicus, Pagria signata, Anomalarufocuprea, Palorus ratzeburgii, Alphitobius laevigatus, Anthrenus verbasci, Lyctus brunneus, Tribolium confusum, Medythia nigrobilineata, Xylotrechus pyrrhoderus, Epitrix cucumeris, Tomicus piniperda, Monochamus alternatus, Popillia japonica, Epicauta gorhami, Sitophilus zeamais, Rhynchites nigrobilineata, Xylotrechus pyrrhoderus, Epitrix cucumeris, Tomicus piniperda, Monochamus alternatus, Popillia japonica, Epicauta gorhami, Sitophilus zeamais, Rhynchites nigrobilineata heros), vegetable leaf weevil (Listroderescostirostris), four-striped bean weevil (Callo sobruchus maculatus), Phyllobius armatus, pear blossom weevil (Anthonomus pomorum), copper leaf beetle (Linaeidea aenea) and Mexican boll weevil (Anthonomusgrandis).

[0406] Examples of Diptera pests include Culex pipiens pallens, Pegomya hyoscyami, Liriomyza huidobrensis, Musca domestica, Chlorops oryzae, Hydrellia sasakii, Agromyza oryzae, Hydrellia griseola, Ophiomyia phaseoli, Dacus cucurbitae, Drosophila suzukii, Rhacochlaena japonica, Muscina stabulans, Megaseliaspiracularis, and other flea flies, Clogmia albipunctata), Tipula aino, Phormia regina, Culex tritaeniorhynchus, Anopheles sinensis, Hylemya brassicae, Asphondylia sp.), Delia platura, Delia antiqua, Rhagoletis cerasi, Culexpipiens 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 tsuneonis), Sitodiplosis mosellana, Meromuza nigriventris, Anastrepha ludens and Rhagoletis pomonella, etc.

[0407] Examples of the Hymenoptera pests include Pristomyrmexpungens, Scleroderma, Monomorium pharaohnis, Pheidole noda, Athalia rosae, Dryocosmus kuriphilus, Formicafusca japonica, wasps, Athalia infumata infumata, Arge pagana, Athalia japonica, Acromyrmex spp., Solenopsis spp., Arge mali, and Ochetellus glaber.

[0408] Examples of the Orthoptera pests include Homorocoryphus lineosus, Gryllotalpa sp., Oxya hyla intricata, Oxya yezoensis, Locusta migratoria, Oxya japonica, Homorocoryphus jezoensis, and Teleogryllus emma.

[0409] Examples of the Thysanoptera pest 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 pasaniae, Scirtothrips citri), Haplothrips chinensis, Mycterothrips glycines, Thrips setosus, Scirtothrips dorsalis, Dendrothrips minowai, Haplothrips niger, Thrips tabaci, Thrips sawaiiensis, Haplothrips kurdjumovi, Chirothrips manicatus, Frankliniella intonsa, Thrips coloratus, Franklinella occidentalis, Thrips palmi, Frankliniella lilivora and Liothrips vaneeckei, etc.

[0410] 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 taiwanensis, and the like. taiwanicus), Acaphylla theavagrans, Polyphagotarsonemus latus, Aculopslycopersici, Ornithonyssus sylvairum, Tetranychus urticae, Eriophyes chibaensis, Sarcoptes scabiei, Haemaphysalis longicornis, Ixodes scapularis, Tyrophagus similis, Cheyletus eruditus, Panonychus citri, Cheyletus moorei, Brevipalpus phoenicis, Octodectes cynotis, Dermatophagoides ptrenyssnus), Haemaphysalis flava, Ixodesovatus, Phyllocoptruta citri, Aculus schlechtendali, Panonychusulmi, Amblyomma americanum, and Dermanyssus gallinaegallinae), Rhyzoglyphus robini, Sancassania sp., etc.

[0411] Examples of Isoptera pests include Reticulitermes miyatakei, Incisitermes minor, Coptotermes formosanus, Hodotermopsis japonica, Reticulitermes sp., Reticulitermes flavicepsamamianus, Glyptotermes kushimensis, Coptotermes guangzhoensis, Neotermes koshunensis, Glyptotermes kodamai, Glyptotermes satsumensis, Cryptotermes domesticus, Odontotermes formosanus, Glyptotermes nakajimai, Pericapritermes nitobei, and Reticulitermes sp. speratus) etc.

[0412] Examples of the Blattaria pests include Periplaneta fuliginosa, Blattella germanica, Blatta orientalis, Periplaneta runnea, Blattella lituricollis, Periplaneta japonica, and Periplaneta americana.

[0413] Examples of the order Siphonaptera include human flea (Pulex irritans), cat flea (Ctenocephalides felis), and chicken horned leaf flea (Ceratophyllus gallinae).

[0414] 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.

[0415] Examples of the mollusks include Pomacea canaliculata, Achatina fulica, Meghimatium bilineatum, Lehmannina valentiana, Limax flavus, and Acusta despecta sieboldiana.

[0416] In addition, the pesticide for agricultural horticulture of the present invention has a strong insecticidal effect on the tomato moth (Tuta absoluta) as other pests.

[0417] In addition, examples of animal parasitic ticks and mites that are one of the control targets include: Boophilus microplus, Rhipicephalus sanguineus, Haemaphysalis longicornis, Haemaphysalis flava, Haemaphysalis campanulata, Haemaphysalis concinna, Haemaphysalis japonica, Haemaphysalis kitaokai, Haemaphysalis ias, Ixodes ovatus, Ixodes nipponensis, Ixodes persulcatus, Amblyomma testudinarium, Haemaphysalis megaspinosa, Dermacentor reticulatus, and Dermacentor taiwanesis); northern fowl mites such as Dermanyssusgallinae, Ornithonyssus sylviarum, and Ornithonyssus bursa; chiggers such as Eutrombicula wichmanni, Leptotrombidium akamushi, Leptotrombidium pallidum, Leptotrombidium fuji, Leptotrombidium tosa, Neotrombiculaautumnalis, Eutrombicula alfreddugesi, and Helenicula miyagawai; and mites such as Cheyletiella yasguri, Cheyletiella sylviarum, and Leptotrombidium fuji. parasitivorax and Cheyletiella blakei;Scabies mites such as Psoroptes cuniculi, Chorioptes bovis, Otodectescynotis, Sarcoptes scabiei, Notoedres cati; and Demodex canis, etc.;

[0418] As other fleas to be controlled, for example, external parasitic wingless insects belonging to the order Siphonaptera, more specifically, fleas belonging to the family Pulicidae and the family Ceratephyllus, etc. Examples of fleas belonging to the family Pulicidae include Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Echidnophaga gallinacea, Xenopsylla cheopis, Leptopsylla segnis, Nosopsyllus fasciatus, and Monopsyllus anisus.

[0419] In addition, as other external parasites to be controlled, for example, there can be mentioned sucking lice such as cattle blind lice (Haematopinus usurysternus), horse blood-sucking lice (Haematopinus asini), sheep lice (Dalmalinia ovis), long-nosed cattle lice (Linognathus vituli), pig blood lice (Haematopinus suis), pubic lice (Phthirus pubis) and head lice (Pediculus capitis); biting lice such as dog biting lice (Trichodectes canis), and blood-sucking dipteran pests such as triangle horsefly (Tabanus trigonus), virtual midge (Culicoides schultzei) and ornament midge (Simulium ornatum). In addition, examples of internal parasites include nematodes such as lungworms, whipworms (Trichuris), tubercle nematodes, gastric parasites, roundworms and filarial worms; tapeworms such as Spirometraerinaceieuropaei, Diphyllobothrium latum, Dipylidium caninum, Taenia multiceps, Echinococcus granulosus and Echinococcus multilocularis; trematodes such as Schistosoma japonicum and Fasciola hepatica; and protozoa such as coccidia, Plasmodium malariae, intestinal Sarcocystis, Toxoplasma gondii, Cryptosporidium, and the like.

[0420] Since the agricultural and horticultural insecticides containing the compounds represented by the general formula (1) of the present invention or their salts as active ingredients have a significant control effect on the pests that damage paddy field crops, dry field crops, fruit trees, vegetables, other crops, flowers, etc., the desired effect of the agricultural and horticultural insecticide of the present invention is achieved by treating the cultivation carriers such as seeds, paddy field water, stems and leaves, or soil of seedling facilities, paddy fields, dry fields, fruit trees, vegetables, other crops, flowers, etc., before the occurrence of pests or at the time when the occurrence of pests is confirmed according to the predicted period of occurrence of pests. Among them, the preferred mode of use is to treat the seedling soil of crops, flowers, etc., the soil of the planting hole during transplantation, the roots of plants, irrigation water, and cultivation water in hydroponic cultivation, and absorb the compounds of the present invention through the soil or without passing through the soil, thereby utilizing the so-called penetration transfer.

[0421] There are no particular limitations on the useful plants to which the agricultural and horticultural pesticide of the present invention can be applied, and examples thereof include: cereals (e.g., rice, barley, wheat, rye, oats, corn, etc.), legumes (soybeans, red beans, broad beans, peas, kidney beans, peanuts, etc.), fruit trees and fruits (apples, citrus fruits, pears, grapes, peaches, plums, cherries, walnuts, chestnuts, almonds, bananas, etc.), leafy and fruity vegetables (cabbage, tomatoes, spinach, broccoli, lettuce, onions, shallots (shallots, shallots), bell peppers, eggplants, strawberries, peppers, okra, leeks, etc.), root vegetables (carrots, potatoes, sweet potatoes, taro, radishes, turnips, lotus roots, burdocks, garlic, scallions, etc.), processed vegetables (e.g., spinach, broccoli, lettuce, onions, shallots, shallots, etc.), Crops for agricultural use (cotton, hemp, beetroot, hops, sugarcane, beet, olive, rubber, coffee, tobacco, tea, etc.), melons (pumpkin, cucumber, watermelon, mulberry, melon, etc.), forage grasses (duckgrass, sorghum, timothy, clover, alfalfa, etc.), zoysia grasses (Korean zoysia, Agrostis, etc.), ornamental crops such as spices (lavender, rosemary, thyme, parsley, pepper, ginger, etc.), flowers (chrysanthemum, rose, carnation, orchid, tulip, lily, etc.), garden trees (ginkgo, cherry, coral wood, etc.), forest trees (fir, spruce, pine, cypress, fir, Japanese cypress, eucalyptus, etc.), etc.

[0422] The "plants" also include plants that have been given resistance to herbicides through classical breeding methods or genetic recombination technology, and the herbicides include: HPPD inhibitors such as isoxathiapiprolin, 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, bromoxynil, dicamba, 2,4-D, etc.

[0423] As examples of "plants" that have been given resistance through classical breeding methods, rapeseed, wheat, sunflower, and rice that are resistant to imidazolinone ALS-inhibiting herbicides such as imazethapyr, and are already sold under the trade name of Clearfield (registered trademark), can be cited. Soybeans that are resistant to sulfonylurea ALS-inhibiting herbicides such as thifensulfuron-methyl can be cited, and are already sold under the trade name of STS soybeans. As examples of plants that have been given resistance to acetyl-CoA carboxylase inhibitors such as trion oximes and aryloxyphenoxypropionic acid herbicides through classical breeding methods, SR corn (Cone) can be cited.

[0424] In addition, plants imparted with resistance to acetyl-CoA carboxylase inhibitors are described in Proceedings of the National Academy of Sciences of the United States of America (Proc. Natl. Acad. Sci. USA) Vol. 87, pp. 7175-7179 (1990) and the like. In addition, mutant acetyl-CoA carboxylases resistant to acetyl-CoA carboxylase inhibitors have been reported in Weed Science, Vol. 53, pp. 728-746 (2005), etc. Such mutant acetyl-CoA carboxylase genes can be introduced into plants by gene recombination technology, or by introducing a mutation associated with imparting resistance into plant acetyl-CoA carboxylase, thereby obtaining plants resistant to acetyl-CoA carboxylase inhibitors. In addition, by introducing a nucleic acid introduced with a base substitution mutation into plant cells, such as the chimeraplasty technology (Gura T. 1999. Repairing the Genome's Spelling Mistakes. Science 285: 316-318.), thereby introducing an amino acid substitution mutation site-specifically into the acetyl-CoA carboxylase gene, ALS gene, etc. of the plant, plants resistant to acetyl-CoA carboxylase inhibitors, ALS inhibitors, etc. can be obtained. The agricultural and horticultural insecticide of the present invention can also be used for these plants.

[0425] In addition, examples of toxins expressed in genetically modified plants include insecticidal proteins derived from Bacillus cereus and Bacillus japonicus; delta-endotoxins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, insecticidal proteins such as VIP1, VIP2, VIP3 or VIP3A, derived from Bacillus thuringiensis; insecticidal proteins derived from nematodes; toxins produced by animals such as scorpion toxins, spider toxins, bee toxins or insect-specific neurotoxins; filamentous fungal toxins; plant lectins; lectins; protease inhibitors such as trypsin inhibitors, serine protease inhibitors, potato tuber storage proteins (Patatin), cysteine ​​protease inhibitors, and papain inhibitors; ricin, corn-RIP, ormosine, rufin, saporin, Bryonia dioica) and other ribosome inactivating proteins (RIP); steroid metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glucosyltransferase, 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.

[0426] In addition, as toxins expressed in such genetically modified plants, there are also mixed toxins, partially deleted toxins, and modified toxins of δ-endotoxin proteins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9C, Cry34Ab or Cry35Ab, insecticidal proteins such as VIP1, VIP2, VIP3 or VIP3A. Using recombinant technology, mixed toxins are produced by new combinations of different domains of these proteins. As partially deleted toxins, Cry1Ab is known to have a part of the amino acid sequence deleted. As modified toxins, one or more amino acids of the natural toxin are replaced.

[0427] Examples of these toxins and recombinant plants capable of synthesizing these toxins are described in EP-A-0374753, WO93 / 07278, WO95 / 34656, EP-A-0427529, EP-A-451878, WO03 / 052073 and the like.

[0428] The toxins contained in these recombinant plants confer resistance to beetle pests, hemiptera pests, diptera pests, lepidoptera pests, nematodes. The agronomic and horticultural pesticides of the present invention can be used in combination with these technologies or in a systemic manner.

[0429] In order to control various pests, the agricultural and horticultural pesticide of the present invention can be directly applied in an amount effective for controlling pests or nematodes, or appropriately diluted with water or the like, or used in a suspended form on plants predicted to have the pests and nematodes. For example, for pests and nematodes occurring in fruit trees, cereals, vegetables, etc., in addition to spreading on stems and leaves, the agricultural and horticultural pesticide of the present invention can be used by treating the soil, etc., such as soaking the seeds in the agent, applying a powder coat to the seeds, treating the seeds with calcium peroxide, mixing the soil in the whole layer, applying strips, mixing the bed soil, treating the seedlings in a tray, treating the planting holes, treating the root system, applying top fertilizer, treating the rice in a box, applying on the water surface, etc., so that the soil can be absorbed by the roots. In addition, the agricultural and horticultural pesticide of the present invention can be used by applying to the nutrient solution in nutrient solution (hydroponics) cultivation, fumigating or injecting into the trunk, etc.

[0430] In addition, the agronomic and horticultural pesticide of the present invention can be used directly or in a suspended form with water or the like in an amount effective for controlling pests at places where the pests are predicted to occur. For example, in addition to being spread on stored grain pests, house pests, sanitary pests, forest pests, etc., it can also be used as a coating, fumigation, bait, etc. on building materials.

[0431] As a method for treating seeds, for example, there can be mentioned: a method of impregnating seeds with a liquid or solid preparation in a diluted or undiluted liquid state to allow the agent to penetrate; a method of mixing a solid preparation or a liquid preparation with seeds and subjecting them to a powder coating treatment so as to adhere to the surface of the seeds; a method of coating the seeds by mixing with an adhesive carrier such as a resin or a polymer; a method of scattering near the seeds while planting, etc.

[0432] 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 cutting cultivation.

[0433] When implementing the method of use of the present invention, the "soil" or "cultivation carrier" of the plant refers to a support for cultivating crops, especially a support for root growth. The material is not particularly limited, as long as it is a material on which plants can grow, and can be so-called soil, seedling mats, water, etc. Specific raw materials include, for example, sand, pumice, vermiculite, diatomaceous earth, agar, gel-like substances, polymer substances, rock wool, glass wool, wood chips, bark, etc.

[0434] The method of spreading the pesticide on the stems and leaves of crops or stored-grain pests, house pests, sanitary pests or forest pests includes: a method of spreading a liquid preparation such as an emulsion or suspension or a solid preparation such as a wettable powder or granular wettable powder by appropriately diluting it with water, a method of spreading a powder, or fumigation.

[0435] Examples of methods for applying to the soil include: a method in which a liquid preparation is diluted with water or undiluted and applied to the roots of a plant or a nursery bed for raising seedlings, a method in which granules are spread on the roots of a plant or a nursery bed for raising seedlings, a method in which powders, wettable powders, granular wettable powders, granules, etc. are spread before sowing or transplanting and mixed with the entire soil, a method in which powders, wettable powders, granular wettable powders, granules, etc. are spread on planting holes, strips, etc. before sowing or planting plants, and the like.

[0436] As a method of applying rice to a nursery box, the formulation may be different depending on the application period, such as application at the time of sowing, application during the greening period, application at the time of transplanting, and the formulation may be applied in the form of powder, granular wettable powder, granules, etc. It can be applied by mixing with the cultivation soil, and the cultivation soil and the powder, granular wettable powder or granules can be mixed, for example, by mixing with the bed soil, mixing with the covering soil, mixing with the entire cultivation soil, etc. The cultivation soil and various formulations can be simply applied by alternately forming layers.

[0437] As a method of applying to paddy fields, solid preparations such as jumbo, packaged preparations, granules, granular wettable powders, and liquid preparations such as flowable preparations and emulsions are usually spread on flooded paddy fields. In addition, appropriate preparations can be spread and injected into the soil directly or mixed with fertilizers during rice transplanting. In addition, it is possible to apply labor-savingly by using liquid medicines such as emulsions and flowable preparations at water inlets, irrigation devices, and other sources of water in paddy fields accompanied by water supply.

[0438] In dry field crops, the cultivation carrier near the seed or plant body can be treated during the period from sowing to seedling raising. In plants directly sown in dry fields, in addition to directly treating the seed, it is preferred to treat the root of the plant in cultivation. Granules can be used for spreading treatment or diluted with water or undiluted agents for irrigation treatment in liquid form. It is also a preferred treatment to mix the granules with the cultivation carrier before sowing and then sow.

[0439] As a treatment for the sowing and seedling raising period of the cultivated plants to be transplanted, in addition to directly treating the seeds, it is preferred to irrigate the nursery bed with a liquid agent or to spread the granules. In addition, treating the planting hole with the granules during field planting or mixing the granules with the cultivation carrier near the transplanting position is also a preferred treatment.

[0440] Usually, the agronomic and horticultural insecticide of the present invention is prepared into a form that is easy to use according to conventional methods for pesticide formulation.

[0441] That is, the compound represented by the general formula (1) of the present invention or its salt can be dissolved, separated, suspended, mixed, impregnated, adsorbed or attached to a suitable inactive carrier or mixed with an auxiliary agent in a suitable ratio as required and then dissolved, separated, suspended, mixed, impregnated, adsorbed or attached to a suitable inactive carrier to prepare a suitable dosage form for use, for example, a suspension, emulsion, liquid, wettable powder, granular wettable powder, granules, powder, tablet, packaging agent, etc.

[0442] In the composition of the present invention (agronomic and horticultural pesticide or animal parasite control agent), in addition to the active ingredients, it may also contain additives commonly used in pesticide preparations or animal parasite control agents as needed. As the additives, there can be mentioned: carriers such as solid carriers and liquid carriers, surfactants, dispersants, wetting agents, adhesives, tackifiers, thickeners, colorants, extenders, spreading agents, antifreeze agents, anti-caking agents, disintegrators, decomposition inhibitors, etc. According to other needs, preservatives, plant pieces, etc. can be used as additives. These additives can be used alone or in combination of two or more.

[0443] As solid carrier, for example, can be enumerated: quartz, clay, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, diatomaceous earth and other natural minerals, calcium carbonate, ammonium sulfate, sodium sulfate, potassium chloride and other inorganic salts, synthetic silicic acid, synthetic silicate, starch, cellulose, plant powder (such as sawdust, coconut shell, corn stalk, tobacco stem, etc.) and other organic solid carriers, polyethylene, polypropylene, polyvinylidene chloride and other plastic carriers, urea, inorganic hollow body, plastic hollow body, fumed silica (fumed silica, white carbon black), etc. These can be used alone or in combination of two or more.

[0444] Examples of the liquid carrier include monovalent alcohols such as methanol, ethanol, propanol, isopropanol, and butanol; alcohols such as polyols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, and glycerol; polyol compounds such as propylene glycol ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, and cyclohexanone; ethers such as ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether, and THF; aliphatic hydrocarbons such as normal alkanes, cycloalkanes, isoalkanes, kerosene, and mineral oil; benzene; , aromatic hydrocarbons such as toluene, xylene, solvent naphtha, alkylnaphthalene, halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, esters such as ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate, dimethyl adipate, lactones such as γ-butyrolactone, amides such as dimethylformamide, diethylformamide, dimethylacetamide, N-alkylpyrrolidone, nitriles such as acetonitrile, sulfides such as dimethyl sulfoxide, vegetable oils such as soybean oil, rapeseed oil, cottonseed oil, castor oil, water, etc. These can be used alone or in combination of two or more.

[0445] Examples of surfactants used as dispersants and wetting agents 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 copolymers, 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 addition acetylene glycols, polyoxyethylene ether-type polysiloxanes, ester-type polysiloxanes, fluorine-based surfactants, polyoxyethylene castor oils, polyoxyethylene curing agents, Nonionic surfactants such as castor oil, alkyl 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, anionic surfactants such as polyoxyethylene alkylphenyl ether phosphates, cationic surfactants such as laurylamine hydrochloride, stearylamine hydrochloride, oleylamine hydrochloride, stearylamine acetate, stearylaminopropylamine acetate, alkylamine salts such as alkyltrimethylammonium chloride and alkyldimethylbenzalkonium chloride, amphoteric surfactants such as amino acid type or betaine type, etc. These surfactants can be used alone or in combination of two or more.

[0446] Examples of the binder and thickener include carboxymethyl cellulose and salts thereof, 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, cross-linked polyvinyl pyrrolidone, copolymers of maleic acid and styrene, (meth)acrylic acid copolymers, half esters of a polymer containing a polyol and a 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.

[0447] 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, and polysaccharides, and inorganic fine powders such as high-purity bentonite and fumed silica (white carbon).

[0448] 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.

[0449] Examples of the antifreeze agent include polyols such as ethylene glycol, diethylene glycol, propylene glycol, and glycerol.

[0450] Examples of auxiliary agents for preventing caking and promoting disintegration include polysaccharides such as starch, alginic acid, mannose, and galactose, polyvinyl pyrrolidone, fumed silica (fumed silica, white carbon), ester gum, petroleum resin, sodium tripolyphosphate, sodium hexametaphosphate, metal stearate, cellulose powder, dextrin, copolymers of methacrylate, polyvinyl pyrrolidone, polyaminocarboxylic acid chelates, sulfonated styrene·isobutylene·maleic anhydride copolymers, starch·polyacrylonitrile graft copolymers, and the like.

[0451] Examples of the decomposition inhibitor include desiccants such as zeolite, quicklime, and magnesium oxide; antioxidants such as phenol compounds, amine compounds, sulfides, and phosphoric acid compounds; and ultraviolet absorbers such as salicylic acid compounds and benzophenone compounds.

[0452] Examples of preservatives include potassium sorbate and 1,2-benzothiazoline-3-one. In addition, 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.

[0453] The mixing ratio of the active ingredient compound can be increased or decreased as needed. In 100 parts by weight of the agronomic and horticultural pesticide of the present invention, it can be appropriately selected and used within the range of 0.01 to 90 parts by weight. For example, in the case of dusts, granules, emulsions or wettable powders, 0.01 to 50 parts by weight (0.01 to 50% by weight relative to the total weight of the agronomic and horticultural pesticide) is appropriate.

[0454] The usage amount of the agricultural and horticultural insecticide of the present invention varies depending on various factors, such as the purpose, target pests, crop development, pest occurrence tendency, weather, environmental conditions, formulation, application method, application location, application period, etc. As the active ingredient compound, it can be appropriately selected from the range of 0.001 g to 10 kg, preferably 0.01 g to 1 kg per 10 ares according to the purpose.

[0455] In order to expand the pests and diseases to be controlled, prolong the optimal control time or reduce the dosage, the agronomic and horticultural insecticide of the present invention can be mixed with other agronomic and horticultural insecticides, acaricides, nematicides, fungicides, biological pesticides, etc., and can also be mixed with herbicides, plant growth regulators, fertilizers, etc. according to the usage.

[0456] Examples of other agricultural and horticultural insecticides, acaricides, and nematicides used for this purpose include 3,5-xylyl methylcarbamate (XMC), fenobucarb (BPMC), Bt toxin insecticidal compounds, chlorfenson (CPCBS), dichlorodiisopropyl ether (DCIP), 1,3-dichloropropene (DD), DDT, NAC, O-4-dimethylsulfamoylphenyl O,O-diethyl phosphorothioate (DSP), O-ethyl O-4-nitrophenyl phenylphosphophenyl (POP), and chlorfenapyr (CPCBS). honothioate (EPN), tripropylisocyanurate (TPIC), acrinathrin, azadirachtin, acynonapyr, azinphos-methyl, acequinocyl, acetamiprid, acetoprole, acephate, abamectin, afidopyropen, avermectin-B, amidoflumet, amitraz, alanycarb, aldicarb, aldoxycarb, aldrin, α-sulfur alpha-endosulfan, alpha-cypermethrin, albendazole, allethrin, isazofos, isamidofos, isoamidofos, isoxathion, isocycloseram, isofenphos, isoprocarb (MIPC), epsilon-metofluthrin, epsilon-momfluorothrin, ivermectin, imicyafos, imidacloprid, imiprothrin, indoxacarb,S-esfenvalerate, ethiofencarb, ethion, ethiprole, etoxazole, ethofenprox, ethoprophos, etrimfos, emamectin, emamectin-benzoate, endosulfan, empenthrin, oxazosulfyl, oxamyl, oxydemeton-methyl, oxydeprofos: ESP, oxibendazole, oxfendazole, Potassium oleate, sodium oleate oleate), cadusafos, kappa-bifenthrin, cartap, carbary1, carbosulfan, carbofuran, gamma-cyhalothrin, xylylcarb, quinalphos, kinoprene, chinomethionat, cloethocarb, clothianidin, tetrametic clofentezine, chromafenozide, chlorantraniliprole, chlorethoxyfos, chlordimeform, chlordane, chlorpyrifos, chlorpyrifos-methyl, chlorphenapyr, chlorfenson, chlorfenvinphos, chlorflua zuron, chlorobenzilate, chlorobenzoate, chloroprallethrin, dicofol, salithion, cyhalodiamide, cyanophos (CYAP), diafenthiuron,diamidafos, cyantraniliprole, theta-cypermethrin, dienochlor, cyetpyrafen, cyenopyrafen, dioxabenzofos, diofenolan, sigma-cypermethrin, cyclaniliprole, dichlofenthion (ECP), cycloprothrin, Dichlorvos (DDVP), dichloromezotiaz, disulfoton, dinotefuran, cyhalodiamide, cyhalothrin, cyphenothrin, cyfluthrin, diflubenzuron, cyflumetofen, diflovidazin, cyproflanilide, cyhexatin, Cypermethrin, dimethylvinphos, dimethoate, dimpropyridaz, dimefluthrin, silafluofen, cyromazine, spidoxamat, spinetoram, spinosad, spirodiclofen, spirotetramat, spiropidion, spiromesifen sifen), sulfluramid, sulprofos, sulfoxaflor, zeta-cypermethrin, diazinon, tau-fluvalinate, dazomet, thiacloprid, thiamethoxam, tioxazafen, thiodicarb, thiocyclam, thiosultap, thiosultap-sodium,thionazin, thiometon, deet, dieldrin, tetrachlorantraniliprole, tyclopyrazoflor, tetrach1orvinphos, tetradifon, tetraniliprole, tetramethylfluthrin, tetramethrin, tebupirimfos, tebufenozide, tebufenpyrad, tefluthrin, teflubenzuron, demeton-S-methyl, temephos, deltamethrin, terbufos, doramectin, tralopyril, tralomethrin, transfluthrin transfluthrin, triazamate, triazuron, trichlamide, trichlorphon (DEP), triflumezopyrium, triflumuron, tolfenpyrad, naled (BRP), nicofluprole, nithiazine, nitenpyram, novaluron, noviflumuron, hydroprene, vaniliprole, vamidothion, parathion, parathion-methyl, halfenprox, halofenozide, bistrifluron, bisultap, hydramethylnon, hydroxypropyl starch propyl starch), binapacryl, pyflubumide, bifenazate, bifenthrin, pymetrozine, pyraclorfos,pyrafluprole, pyridafenthion, pyridaben, pyridalyl, pyrifluquinazon, pyriprole, pyriproxyfen, pirimicarb, pyrimidifen, pyriminostrobin, pirimiphos-methyl, pyrethrins, fipronil, fenamicarb azaquin), fenamiphos, bromopropylate, fenitrothion (MEP), fenoxycarb, 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、flupyrazofos、flupyrimin、flufenerim、flufenoxystrobin、flufenoxuron、flufenzine、flufenoprox, fluproxyfen, flubrocythrinate, fluhexafon, flubendiamide, flupentiofenox, flumethrin, flurimfen, prothiofos, protrifenbute, flonicamid, propaphos, propargite (BPPS), profenofos, broflanilide, profluthrin, propoxur (PHC), flometoquin, alpha-bromadiolone, bromopropylate, beta-cyfluthrin, flumetoquin, Urea (hexaflumuron), hexythiazox, heptafluthrin, heptenophos, permethrin, benclothiaz, bendiocarb, benzpyrimoxan, bensulphide, benzoximate, benfuracarb, phoxim, phosalone, fosthiazate, fosthietia, phosphamidon, phosphocarb, phosmet:PMP, polynactins, formetanate, formothion, phorate, machine oil oil), malathion, milbemycin, milbemycin-A, milbemectin, mecarbam, mesulfenfos, methomyl, metaldehyde, metaflumizone, methamidophos, metam-ammonium, metam-sodium, methiocarb,Methidathion (DMTP), methylisothiocyanate, methylneodecanamide, methylparathion, 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, cyhexatin, calcium cyanamide, calcium polysulfide, sulfur and nicotine-sulfate, etc.

[0457] 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, and chloranil. alcohol), 4-dodecyl-2,6-dimethylmorpholine (aldimorph), amobam, isotianil, isovaledione, isopyrazam, isofetamid, isofluxypram, isoprothiolane, ipconazole, ipfentrifluconazole, ipflufenoquin, iprodione, iprovalicarb, iprobenfos, imazalil, iminoctadine, metam, iminoctadine-albesilate, iminoctadine-triacetate, imibe nconazole), inpyrfluxam, uniconazole, uniconazole-P, echlomezole, edifenphos, etaconazole, ethaboxam, ethirimol, etem, ethoxyquin, etridiazole, enestroburin, enoxastrobin, epoxiconazole, oxadixyl, oxathiapiprolin, oxycarboxin, copper-8-quinolinolate, oxytetracycline, copper-oxinate,Oxpoconazole, oxpoconazole-fumarate, oxolinic acid, octhilinone, ofurace, orysastrobin, carbam, metam-sodium, kasugamycin, carbamorph, carpropamid, carbendazim, carboxin, carvone, quinazamid, quinacetol, quinoxyfen, quinofumelin, chinomethionat, quinomethionat ate), captafol, captan, kiralaxyl, quinconazole, quintozene, guazatine, cufraneb, cuprobam, coumoxystrobin, glyodin, griseofulvin, climbazole, cresol, kresoxim-methyl, chlozolinate, clotrimazole, chloben thiazone), chloraniformethan, chloranil, chlorquinox, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, chloroneb, salicylanilide, zarilamid, cyazofamid, diethylpyrocarbonate, diethofencarb, cyclafuramid, diclocymet, dichlozoline, diclobutrazol, cyclobutrifluram,dichlofluanid, cycloheximide, dichlobentiazox, diclomezine, dicloran, dichlorophen, dichlone, disulfiram, ditalimfos, dithianon, diniconazole, diniconazole-M, zineb, dinocap, dinoct on), dinosulfon, dinoterbon, dinobuton, dinopenton, dipymetitrone, dipyrithione, diphenylamine, difenoconazole, cyflufenamid, diflumetorim, cyproconazole, cyprodinil, cyprofuram, cypendazol e), simeconazole, dimethirimol, dimethomorph, cymoxanil, dimoxystrobin, ziram, silthiofam, streptomycin, spiroxamine, sultropen, 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, 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, coppernonylphenol sulfonate, halacrinate, validamycin, valifenalate, harpin protein), picarbutrazox, bixafen, picoxystrobin, picobenzamide, pydiflumetofen, bithionol, bitertanol, hydroxyisoxazole, hydroisoxazole-potassium, binapacryl, biphenyl, piperalin, hymexazol, pyraoxystrobin, pyracarbolid,pyraclostrobin, pyraziflumid, pyrazophos, pyrapropoyne, pyrametostrobin, pyriofenone, pyridinitril, pydiflumetofen, pyrifenox, pyrisoxazole, pyridachlometyl, pyrifenox, pyribencarb, pyriminostrobin , pyrimethanil, pyroxychlor, pyroxyfur, pyroquilon, vinclozolin, ferbam, famoxadone, fenapanil, fenamidone, fenaminosulf, fenaminstrobin, fenarimol, fenitropan, fenoxanil, ferimzon one), ferbam, fentin, fenpiclonil, fenpicoxamid, fenpyrazamine, fenbuconazole, fenfuram, fenpropidin, fenpropimorph, fenhexamid, phthalide, buthiobate, butylamine, bupirimate, fuberidazolidine, ole), blasticidin-S, furametpyr, furaxyl, fluacrypyrim, fluazinam, fluindapyr, fluoxastrobin, fluoxapiprolin, fluoxytioconazole, fluotrimazole, fluopicolide, Fluopimomide, fluopyram, fluoroimide,furcarbanil, fluxapyroxad, fluquinconazole, furconazole, furconazole-cis, fludioxonil, flusilazole, flusulfamide, flutianil, flutolanil, flutriafol, flufenoxadiazam, flufenoxystrobin, furfural, flubeneteram, furmecyclox, flumetylsulforim, flumetover, 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 acid), benzovindiflupyr, bentaluron, benthiazole, benthiavalicarb, benthiavalicarb-isopropyl, penthiopyrad, penflufen, boscalid, phosdiphen, fosetyl,Fosetyl-Al, polyoxins, polyoxorim, polycarbamate, folpet, formaldehyde, machine oil, maneb, mancozeb, mandipropamid, mandestrobin, myclozolin, myclobutanil, mildiomycin, milneb, mecarbinzid, methasulfocarb, metazoholon, metam, metam-sodium, metalaxyl, metalaxyl-M, metarylpicoxamid, 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, silver and other inorganic sterilants, sodium hypochlorote, cupric hydroxide, wettable sulfur, calcium sulfur polysulfide), potassium hydrogen carbonate, sodium hydrogen carbonate, inorganic sulfur,Copper compounds such as copper sulfate anhydride, nickel dimethyldithiocarbamate, 8-hydroxyquinoline copper, zinc sulfate, and copper sulfate pentahydrate.

[0458] 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, MCPA ethylthioester, MCPB, ioxynil, aclonifen, and pyraclostrobin. azafenidin, acifiuorfen, 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, isocarbamid, isoxachlortole, isoxapyrif op), isoxaflutole, isoxaben, isocil, isonoruron, isoproturon, isopropalin, isopolinate, isomethiozin, inabenfide, ipazine, ipfencarbazone, iprymidam, imazaquin, imazapic, imazapyr, imazamethapyr, imazamethabenz, imazamethabenz-methyl,Imazamox, imazethapyr, imazosulfuron, indaziflam, indanofan, indolebutyric acid, uniconazole-P, eglinazine, esprocarb, ethametsulfuron, ethametsulfuron-methyl, ethalfluralin, ethiolate, ethychlozate ethyl), ethidimuron, etinofen, ethephon, ethoxysulfuron, ethoxyfen, etnipromid, ethofumesate, etobenzanid, epyrifenacil, epronaz, erbon, endothal, oxadiazon, oxadiargyl, oxaziclomefone, oxasulfuron, oxapyrazon, 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, chloranil methoxynil), chlomethoxyfen, clomeprop, chlorazifop, chlorazine, chloranocryl, chloramben, cloransulam, cloransulam-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorsulfuron, chlortha l), chlorthiamid, chlortoluron, chlornitrofen, chlorfenac, chlorfenprop, chlorbufam, chlorphthalim, chlorflurazole, chlorflurenol, chlorprocarb, chlorpropham, chlormequat, chloreturon, chlorchlorpyrifos ... oroxynil), chloroxuron, chlorotoluron, chloropon, saflufenacil, cyanazine, cyanatryn, di-allate, diuron, diethamquat, dioxopyritrione, dicamba, cycluron, cycloate, cycloxydim, diclosulam,Cyclosulfamuron, cyclopyranil, cyclopyrimorate, dichlorprop, dichlorprop-P, dichlobenil, diclofop, diclofop-methyl, dichlormate, dichloralurea, diquat, cisanilide, disul, siduron, dithiopyr ithiopyr), diinitramine, cinidon-ethyl, dinosam, cinosulfuron, dinoseb, dinoterb, dinofenate, dinoprop, cyhalofop-butyl, cypyrafluone, diphenamid, difenoxuron, difenopenten, difenzoquat, cyb utryne), cyprazine, cyprazole, diflufenican, diflufenzopyr, dipropetryn, cypromid, cyperquat, gibberellin, simazine, dimexano, dimesulfazet, dimethachlor, dimidazon, dimethametryn, dimeth henamid), simetryn, simeton, dimepiperate, dimefuron, cinmethylin, swep, sulglycapin, sulcotrione, sulfallate, sulfentrazone, sulfosulfuron, sulfometuron, sulfometuron-methyl, secbumeton,Sethoxydim, sebuthylazine, terbacil, daimuron, dazomet, dalapon, thiazafluron, thiazopyr, tiafenacil, thiencarbazone, thiencarbazone-methyl, tiocarbazil, tioclorim, thiobencarb, thiadiazole (thidiazimin), thidiazuron, thifensulfuron, thifensulfuron-methyl, desmedipham, desmetryn, tetflupyrolimet, tetrafluron, thenylchlor, tebutam, tebuthiuron, terbumeton, tepraloxydim, tefuryltr ione), 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, trimeturon, tolpyralate, naptalam, naproanilide, naproxenamide, nicosulfuron, nitralin, nitrofen, nitrofluorfen, nipyraclofen, neburon, norflur azon), noruron, barban, paclobutrazol, paraquat, parafluron, haloxydine, halauxifen, haloxyfop, haloxyfop-P, haloxyfop-methyl, halosafen, halosulfuron, halosulfuron-methyl, bialaninphos ilanafos), bixlozone, picloram, picolinafen, bicyclopyrone, bispyribac, bispyribac-sodium, pydanon, pinoxaden, bipyrazone, bifenox, piperophos, hymexazol, pyraclonil, pyrasulfotole , pyrazoxyfen, pyrazosulfuron, pyrazosulfuron-ethyl, pyrazolate, bilanfos, pyraflufen-ethyl, pyriclor, pyridafol, pyrithiobac, pyrithiobac-sodium, pyridate, pyriftalid, pyributicarb,pyribenzoxim, pyrimisulfan, primisulfuron, pyriminobac-methyl, pyroxasulfone, pyroxsulam, fenasulam, phenisopham, fenuron, fenoxasulfone, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl thy1), phenothiol, fenoprop, phenobenzuron, fenquinotrione, fenthiaprop, fenteracol, fentrazamide, fenpyrazone, phenmedipham, phenmedipham-ethyl, butachlor, butafenacil, butamifos, buthi uron), buthidazole, butylate, buturon, butenachlor, butroxydim, butralin, butroxydim, flazasulfuron, flamprop, furyloxyfen, prynachlor, primisulfuron-methyl, fluazifop, fluazifop-methyl p-P), fluazifop-butyl, fluazolate, fluroxypyr, fluothiuron, fluometuron, fluoroglycofen, flurochloridone, fluorodifen, fluoronitrofen, fluoromidine, flucarbazone, flucarbazone-sodium,fluchloralin, flucetosulfuron, fluthiacet, fiuthiacet-methyl, flupyrsulfuron, flufenacet, flufenican, flufenpyr, flupropacil, flupropanate, flupoxam, flumioxazin, flumiclorac , flumiclorac-pentyl, flumipropyn, flumezin, fluometuron, flumetsulam, fluridone, flurtamone, fluroxypyr, pretilachlor, proxan, proglinazine, procyazine, prodiamine, prosulfalin, prosulfuron, prosulfocarb, propaquizafop, propachlor, propazine, propanil, propyzamide, propisochlor, prohydrojasmon, propyrisulfuron, propham, profluazol, profluralin, prohexadone e-calcium), propoxycarbazone, propoxycarbazone-sodium, profoxydim, bromacil, brompyrazon, prometryn, prometon, bromoxynil, bromofenoxim, bromobutide, bromobonil, florasulam, florpyrauxifen,Hexachloroacetone, hexazinone, pethoxamid, benazolin, penoxsulam, pebulate, beflubutamid, beflubutamid-M, vernolate, perfluidone, bencarbazone, benquitrione, benzadox, benzipram, benzylaminopurine, benzthiazuron, benzfendizone, bensulide ), bensulfuron-methyl, benzoylprop, benzobicyclon, benzofenap, benzofluor, bentazone, pentanochlor, benthiocarb, pendimethalin, pentoxazone, benfluralin, benfuresate, fosamine, fomesafen, foramsulfuron, forchlorfenuron, maleic hyd razide), mecoprop, mecoprop-P, menoterb, mesosulfuron, mesosulfuron-methyl, mesotrione, mesoprotryne, metazachlor, methazole, metazosulfuron, methabenzthiazuron, metamitron, metamifop, metam, methalpropalin, methiuron, methiozolin, methiobencarb,methyldymron, metoxuron, metosulam, metsulfuron, metsulfuron-methyl, metflurazon, metobromuron, metobenzuron, methometon, metolachlor, metribuzin, mepiquat-chloride, mefenacet, mefluidide, monalide, monisouron, monuron, monochloroacetic acid, monolinuron, molinate, morf amquat), iodosulfuron, iodosulfuron-methyl-sodium, iodobonil, iodomethane, lactofen, lancotrione, linuron, rimisoxafen, rimsulfuron, lenacil, rhodethanil, calcium peroxide, and methylbromide.

[0459] 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, Pasteurella penetrantis, Trichoderma lignorum, Agrobacterium radiobactor, non-pathogenic Erwinia carotovora, Bacillus subtilis, etc. Subtilis or other microbial pesticides used as fungicides, or Xanthomonas campestris or other biopesticides used as herbicides, can be used in combination to achieve the same effect.

[0460] In addition, as a biopesticide, it can be used in combination with the following ingredients, for example: 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.

[0461] Example

[0462] Representative embodiments of the present invention are exemplified below, but the present invention is not limited thereto.

[0463] Manufacturing Example 1

[0464] Preparation of N-(4-fluorophenyl)-5-hydroxy-3-oxo-1-(4-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridazine-4-carboxamide (Compound No. 1-7)

[0465] [Chemical formula 14]

[0466]

[0467] 5-Hydroxy-3-oxo-1-(4-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridazine-4-carboxylic acid ethyl ester (0.15 g, 0.45 mmol) was mixed with toluene (5 ml), 4-fluoroaniline (0.06 g, 0.54 mmol) was added dropwise thereto, and ethanol was removed using a Dean-Stark apparatus under heating and reflux, and stirred for 2 hours. After the reaction solution was cooled, the crude reaction product obtained by concentrating under reduced pressure was purified by silica gel column chromatography to obtain the title compound (0.05 g).

[0468] Yield: 28%

[0469] Physical properties: Melting point 65-70℃

[0470] Manufacturing Example 2

[0471] Preparation of N-(4-fluorophenyl)-1-(6-chloropyridin-3-yl)-5-hydroxy-3-oxo-1,2,3,6-tetrahydropyridazine-4-thioamide (Compound No. 2-3)

[0472] [Chemical formula 15]

[0473]

[0474] 1-(6-chloropyridin-3-yl)-5-hydroxy-1,6-dihydropyridazine-3(2H)-one (0.10 g, 0.44 mmol) was dissolved in dimethylformamide (3.0 mL), cesium carbonate (0.17 g, 0.53 mmol) was added thereto, and 4-fluorophenyl isothiocyanate (0.11 g, 0.71 mmol) was slowly added dropwise, and stirred at room temperature for 2 hours. 1N hydrochloric acid (10 mL) was slowly added to the solution after the reaction, and ethyl acetate (10 mL) was added for liquid separation. The aqueous layer was extracted twice with ethyl acetate (10 mL), and the combined organic layers were washed once with saturated brine (10 mL), and then anhydrous sodium sulfate was added for drying. The crude product obtained by concentrating the solution under reduced pressure was purified by silica gel column chromatography to obtain the title compound (0.02 g).

[0475] Yield: 12%

[0476] Physical properties: Melting point 230-233℃

[0477] Manufacturing Example 3

[0478] Preparation of N-(4-fluorophenyl)-1-(6-trifluoromethylpyridin-3-yl)-5-hydroxy-3-thioxo-1,2,3,6-tetrahydropyridazine-4-carboxamide (Compound No. 2-5)

[0479] [Chemical formula 16]

[0480]

[0481] A solution of N-(4-fluorophenyl)-5-hydroxy-3-oxo-1-(4-trifluoromethylpyridin-3-yl)-1,2,3,6-tetrahydropyridazine-4-carboxamide (0.10 g, 0.25 mmol) in toluene (10 mL) was added to Lawesson's reagent (0.056 g, 0.14 mmol) and stirred for 2 hours under heating reflux. After the reaction was completed, the reaction solution was concentrated by a rotary evaporator. The obtained residue was dissolved in ethyl acetate and purified by silica gel chromatography. The obtained crystals were washed and filtered with n-hexane / methyl tert-butyl ether to obtain the title compound (0.055 g, 0.13 mmol).

[0482] Yield: 52%

[0483] Physical properties: Melting point 182-184℃

[0484] Reference Example 1

[0485] Production of 1-diphenylmethylene-2-(4-trifluoromethylphenyl)hydrazine

[0486] [Chemical formula 17]

[0487]

[0488] 4-Trifluoromethylphenylhydrazine (5.28 g, 30.0 mmol) was dissolved in ethanol (50 mL), benzophenone (5.28 g, 29 mmol) and acetic acid (5.40 g, 90 mmol) were added thereto, and the mixture was stirred under heating reflux for 2 hours. After the reaction solution was cooled, the crude reaction product obtained by concentrating under reduced pressure was purified by silica gel column chromatography to obtain the title compound (9.4 g).

[0489] Yield: 92%

[0490] Reference Example 2

[0491] Preparation of methyl 2-{2-diphenylmethylene-1-(4-trifluoromethylphenyl)hydrazino}acetate

[0492] [Chemical formula 18]

[0493]

[0494] 60% sodium hydride (1.2 g, 30.0 mmol) was suspended in dimethylacetamide (20 mL), and a solution of 1-diphenylmethylene-2-(4-trifluoromethylphenyl)hydrazine (8.51 g, 25.0 mmol) in dimethylacetamide (10 mL) was slowly added dropwise under ice cooling, and stirred for 10 minutes. Methyl bromoacetate (4.97 g, 32.5 mmol) was slowly added dropwise, and the mixture was warmed to room temperature and stirred for 2 hours. The reacted solution was slowly poured into ice water (30 mL), and extracted three times from the aqueous layer with ethyl acetate (30 mL). The combined organic layer was washed once with saturated brine (30 mL), and dried by adding anhydrous sodium sulfate. The crude reaction product obtained by concentrating the solution under reduced pressure was purified by silica gel column chromatography to obtain the title compound (7.0 g).

[0495] Yield: 68%

[0496] Reference Example 3

[0497] Preparation of methyl 2-{1-(4-trifluoromethylphenyl)hydrazino}acetate

[0498] [Chemical formula 19]

[0499]

[0500] Methyl 2-{2-diphenylmethylene-1-(4-trifluoromethylphenyl)hydrazine}acetate (6.58 g, 15.7 mmol) was dissolved in a mixed solution of ethanol (50 mL) and 2-methyltetrahydrofuran (10 mL), and concentrated hydrochloric acid (10 mL) was added dropwise thereto, and stirred at room temperature for 3 hours. After the solution after the reaction was concentrated under reduced pressure, water (50 mL) was added, and potassium carbonate was added to make it weakly alkaline. The aqueous layer was extracted three times with ethyl acetate (50 mL), and the combined organic layers were washed once with saturated brine (50 mL), and then dried by adding anhydrous sodium sulfate. The crude reaction product obtained by concentrating the solution under reduced pressure was purified by silica gel column chromatography to obtain the title compound (3.65 g).

[0501] Yield: 94%

[0502] Reference Example 4

[0503] Preparation of ethyl 3-{2-(2-methoxy-2-oxoethyl)-2-(4-trifluoromethylphenyl)hydrazine}-3-oxopropanoate

[0504] [Chemical formula 20]

[0505]

[0506] 2-{1-(4-trifluoromethylphenyl)hydrazine}acetic acid methyl ester (3.65g, 14.7mmol) was mixed with chloroform (20mL), and monoethyl malonate (3.88g, 29.4mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (5.64g, 29.4mmol), and 4-dimethylaminopyridine (3.59g, 29.4mmol) were added thereto in sequence, and stirred at room temperature for 2 hours. Water (50mL) and chloroform (50mL) were added to the solution after the reaction for liquid separation. The obtained organic layer was washed once with 10% hydrochloric acid (50mL) and once with saturated brine (50mL), and anhydrous sodium sulfate was added for drying. The crude reaction product obtained by concentrating the solution under reduced pressure was purified by silica gel column chromatography to obtain the title compound (3.9g).

[0507] Yield: 73%

[0508] Reference Example 5

[0509] Preparation of 5-hydroxy-3-oxo-1-(4-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridazine-4-carboxylic acid ethyl ester (Compound No. 5-29)

[0510] [Chemical formula 21]

[0511]

[0512] Ethyl 3-{2-(2-methoxy-2-oxoethyl)-2-(4-trifluoromethylphenyl)hydrazine}-3-oxopropanoate (1.1 g, 3.0 mmol) was dissolved in super dehydrated ethanol (10 mL) under an argon atmosphere, and a 20% sodium ethoxide ethanol solution (2.04 g, 6.0 mmol) was slowly added dropwise thereto, and stirred at 60°C for 1 hour. After the solution after the reaction was cooled, water (30 mL) and ethyl acetate (20 mL) were added to the crude reaction product obtained by concentrating under reduced pressure for separation, and 10% hydrochloric acid was added to the obtained water layer to make it acidic. The water layer was extracted 3 times with ethyl acetate (30 mL), and the combined organic layers were washed once with saturated brine (30 mL), and anhydrous sodium sulfate was added for drying. After the solution was concentrated under reduced pressure, the precipitated crystals were washed with a mixed solution of n-hexane and ethyl acetate to obtain the title compound (0.35 g).

[0513] Yield: 35%

[0514] Reference Example 6

[0515] Preparation of 5-hydrazino-2-trifluoromethylpyridine

[0516] [Chemical formula 22]

[0517]

[0518] 5-amino-2-trifluoromethylpyridine (9.73 g, 60.0 mmol) was dissolved in concentrated hydrochloric acid (80 mL), and an aqueous solution of sodium nitrite (4.55 g, 66.0 mmol) dissolved in water (20 mL) was slowly added dropwise under ice cooling for 30 minutes while adjusting the temperature of the reaction solution to no more than 10 ° C. After the addition was completed, it was stirred at the same temperature for 30 minutes. In a separately prepared reaction tank, tin (II) chloride (22.75 g, 120.0 mmol) was dissolved in concentrated hydrochloric acid (20 mL). The solution of the diazonium salt prepared as above was slowly added dropwise under ice cooling while adjusting the temperature of the reaction solution to no more than 10 ° C. After the addition was completed, it was warmed to room temperature and stirred for 2 hours. In the reacted solution, sodium hydroxide aqueous solution was added under ice cooling to make it alkaline, and then diatomaceous earth filtration was performed, and ethyl acetate (200 mL) was added to the obtained filtrate for liquid separation. The aqueous layer was extracted twice with ethyl acetate (100 mL), the combined organic layers were washed once with saturated brine (100 mL), and then dried by adding anhydrous sodium sulfate. The crude reaction product obtained by concentrating the solution under reduced pressure was purified by silica gel column chromatography to obtain the title compound (7.0 g).

[0519] Yield: 66%

[0520] Reference Example 7

[0521] Preparation of 2-hydrazino-5-trifluoromethylpyridine

[0522] [Chemical formula 23]

[0523]

[0524] 2-Bromo-5-trifluoromethylpyridine (4.52 g, 20.0 mmol) was dissolved in ethanol (30 mL), hydrazine monohydrate (8.0 g, 160.0 mmol) was slowly added dropwise thereto, and the mixture was stirred under heating and reflux for 3 hours.

[0525] After cooling the solution after the reaction, add water (10mL) and concentrate under reduced pressure. Add water (20mL) and ethyl acetate (30mL) to the obtained concentrate for separation. Extract twice with ethyl acetate (30mL) from the water layer, wash the combined organic layers with saturated brine (30mL) once, and add anhydrous sodium sulfate for drying. The crude reaction product obtained by concentrating the solution under reduced pressure is purified by silica gel column chromatography to obtain the title compound (3.50g).

[0526] Yield: 99%

[0527] Reference Example 8

[0528] Preparation of 1-(6-chloropyridin-3-yl)-5-hydroxy-1,6-dihydropyridazin-3(2H)-one (Compound No. 4-28)

[0529] [Chemical formula 24]

[0530]

[0531] Ethyl 1-(6-chloropyridin-3-yl)-5-hydroxy-3-oxo-1,2,3,6-tetrahydropyridazine-4-carboxylate (1.0 g, 3.4 mmol) was suspended in a mixed solution of acetonitrile (10 mL) and water (1 mL), and stirred under heating reflux for 2 hours. After the reaction solution was cooled, the crude reaction product obtained by concentrating under reduced pressure was purified by silica gel column chromatography to obtain the title compound (0.58 g).

[0532] Yield: 76%

[0533] The following is a preparation example, but the invention is not limited thereto. In the preparation example, part means part by weight.

[0534] Preparation Example 1.

[0535]

[0536] The above ingredients are uniformly mixed and dissolved to prepare an emulsion.

[0537] Preparation Example 2.

[0538] 3 parts of the compound of the present invention

[0539] Clay powder 82 parts

[0540] 15 parts of diatomaceous earth powder

[0541] The above ingredients are uniformly mixed and crushed to form a powder.

[0542] Preparation Example 3.

[0543] 5 parts of the compound of the present invention

[0544] 90 parts of mixed powder of bentonite and clay

[0545] Calcium lignin sulfonate 5 parts

[0546] The above are uniformly mixed, and a suitable amount of water is added for kneading, granulation, and drying to prepare granules.

[0547] Preparation Example 4.

[0548] 20 parts of the compound of the present invention

[0549] Kaolin and synthetic highly dispersed silicate 75 parts

[0550] 5 parts of a mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzene sulfonate

[0551] Mix the above ingredients evenly and grind them into wettable powder.

[0552] Examples of biological tests are shown below, but the present invention is not limited thereto.

[0553] Test Example 1. Insecticidal test against Plutella xylostella

[0554] Adults of Plutella xylostella were released into cabbage seedlings to lay eggs. Two days after release, the cabbage seedlings with the eggs were immersed in a 500 ppm solution of a drug containing the compound represented by the general formula (1) of the present invention as an active ingredient for about 30 seconds, air-dried, and then left to stand in a constant temperature room at 25°C. After 6 days of immersion in the drug solution, the number of hatched insects was investigated, the mortality rate was calculated by the following formula, and the judgment was made according to the following judgment criteria. 10 heads per zone, 3-unit system.

[0555] [Mathematical formula 1]

[0556]

[0557] Judgment criteria.

[0558] A. Dead insect rate 100%

[0559] B. Insect death rate 99% to 90%

[0560] C. Insect death rate 89% to 80%

[0561] D. Insect death rate: 79% to 50%

[0562] E. Dead insect rate 49% to 0%

[0563] As a result, among the compounds represented by the general formula (1) of the present invention, compound numbers 1-4, 1-7, 1-9, 1-11, 1-14, 1-16, 1-18, 1-21, 1-23, 1-26, 1-27, 1-28, 1-29, 1-30, 1-33, 1-35, 1-36, 1-37, 1-38, 1-39, 1-40, 1-42, 1-43, 1-44, 1-45, 1-46, 1-47, 1-48, 1-49, 1-50, 1-51, 1-52, 1-53, 1-54, 1-55, 1-56, 1-57, 1-58, 1-59, 1-62, 1-63, 1-67, 1-68, 1-69, 1-70, 1-71 -73, 1-121, 1-122, 1-123, 1-124, 1-127, 1-128, 1-129, 1-130, 1-131, 1-132, 1-133, 1-134, 1-137, 1-138, 1-139, 1-140, 1-143, 1-144, 1-146, 1-147, 1-148, 1-149, 1-151, 1-152, 1-153, 1-154, 1-157, 1-158, 1-159, 1-160, 1-162, 1-163, 1-164, 1-167, 1-168, 1-170, 1-172, 1-173, 1-175, 1-176, 1-179 , 1-182, 1-183, 1-184, 1-186, 1-187, 1-188, 1-189, 1-191, 1-192, 1-193, 1-194, 1-195, 1-196, 1-197, 1-198, 1-199, 1-202, 1-203, 1-204, 1-205, 1-2 06, 1-212, 1-215, 1-216, 1-218, 1-221, 1-222, 1-227, 1-229, 1-230, 1-233, 1-235, 1-236, 1-237, 1-238, 1-239, 1-240, 1-241, 1-242, 1-243, 1-244, 1- 245, 1-246, 1-247, 1-248, 1-249, 1-250, 1-256, 1-257, 1-258, 1-260, 1-261, 1-263, 1-264, 1-275, 1-276, 1-277, 1-278, 1-279, 1-280, 1-281, 1-282, 1 -283, 1-284, 1-285, 1-286, 1-287, 1-288, 1-289, 1-290, 1-291, 1-292, 1-293, 1-294, 1-295, 1-296, 1-297, 1-298, 1-299, 1-300, 1-301, 1-302, 1-303,The compounds of 1-304, 1-305, 1-306, 1-310, 1-311, 1-312, 1-314, 1-315, 1-316, 1-317, 1-318, 2-3, 2-4, 2-5, 2-6, 2-7, 2-8, 2-9, 2-10, 2-11, 2-12, 2-14, 2-16, 2-18, 2-19, 2-20 and 3-2 showed excellent activity against Plutella xylostella in the A-judgment.

[0564] Test Example 2. Insecticidal test against Laodelphax striatella

[0565] 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.

[0566] [Mathematical formula 2]

[0567]

[0568] As a result, among the compounds represented by the general formula (1) of the present invention, compound numbers 1-4, 1-7, 1-9, 1-18, 1-11, 1-14, 1-21, 1-23, 1-26, 1-27, 1-28, 1-29, 1-30, 1-33, 1-35, 1-36, 1-37, 1-38, 1-39, 1-40, 1-42, 1-43, 1-44, 1-45, 1-46, 1-47, 1-48, 1-49, 1-50, 1-51, 1-52, 1-53, 1-54, 1-56, 1-57, 1-58, 1-62, 1-63, 1-66, 1-67, 1-68, 1-69, 1-70, 1-73, 1-89, 1-90 -121, 1-122, 1-123, 1-124, 1-127, 1-128, 1-129, 1-130, 1-132, 1-133, 1-134, 1-137, 1-138, 1-139, 1-140, 1-143, 1-144, 1-145, 1-146, 1-147, 1-148, 1-151, 1-152, 1-153, 1-154, 1-155, 1-157, 1-158, 1-162, 1-163, 1-164, 1-167, 1-168, 1-170, 1-172, 1-173, 1-174, 1-175, 1-176, 1-183, 1-184, 1-185 , 1-186, 1-187, 1-188, 1-189, 1-190, 1-191, 1-192, 1-193, 1-194, 1-195, 1-196, 1-197, 1-198, 1-199, 1-200, 1-201, 1-202, 1-203, 1-204, 1-205, 1-2 06, 1-207, 1-209, 1-211, 1-212, 1-213, 1-214, 1-215, 1-216, 1-217, 1-218, 1-220, 1-221, 1-222, 1-224, 1-225, 1-230, 1-232, 1-236, 1-237, 1-238, 1- 239, 1-241, 1-242, 1-244, 1-245, 1-246, 1-247, 1-248, 1-249, 1-250, 1-251, 1-252, 1-254, 1-255, 1-256, 1-257, 1-258, 1-259, 1-260, 1-261, 1-263, 1 -264, 1-265, 1-275, 1-276, 1-277, 1-278, 1-279, 1-280, 1-281, 1-282, 1-283, 1-284, 1-285, 1-286, 1-287, 1-288, 1-289, 1-290, 1-291, 1-292, 1-293,1-294, 1-295, 1-296, 1-297, 1-298, 1-299, 1-300, 1-301, 1-302, 1-303, 1-304, 1-305, 1-306, 1-308, 1-310, 1-311, 1-312, 1-313, 1-314, 1-315, 1-316, 1-317, 1- The compounds of 3-18, 2-3, 2-4, 2-5, 2-6, 2-7, 2-8, 2-9, 2-10, 2-11, 2-12, 2-14, 2-15, 2-16, 2-17, 2-18, 2-19, 2-20, 3-1 and 3-2 showed excellent activity against Laodelphax striatellus in A judgment.

[0569] Test Example 3. Insecticidal test against western flower thrips (Frankliniella occidentalis)

[0570] Female adult flower thrips were inoculated onto lentil leaves fixed on an agar medium, and after 1 day of egg laying, the female adult was removed. Then, after 3 days, the number of hatched larvae on the leaves was counted, and then a solution containing the compounds described in Tables 1 to 3 as active ingredients diluted to 500 ppm was spread. The number of larvae of the species that survived 4 days after the treatment was investigated, and the mortality rate was calculated by the following formula, which was carried out according to the judgment criteria of Test Example 1. 2-way system.

[0571] [Mathematical formula 3]

[0572]

[0573] As a result, among the compounds represented by the general formula (1) of the present invention, compound numbers 1-4, 1-7, 1-9, 1-14, 1-18, 1-21, 1-23, 1-26, 1-27, 1-28, 1-29, 1-30, 1-33, 1-35, 1-37, 1-38, 1-39, 1-40, 1-42, 1-43, 1-44, 1-45, 1-46, 1-47, 1-48, 1-49, 1-50, 1-51, 1-52, 1-53, 1-54, 1-55, 1-57, 1-58, 1-59, 1-62, 1-63, 1-67, 1-68, 1-69, 1-70, 1-73, 1-89, 1-121, 1-122, 1-123, 1-124, 1-127, 1-128, 1-129, 1-130, 1-131, 1-132, 1-133, 1-134, 1-137, 1-138, 1-139, 1-140, 1-143, 1-144, 1-145, 1-146, 1-147, 1-148, 1-149, 1-150, 1-151, 1-152, 1-153, 1-154, 1-155, 1-157, 1-158, 1-159, 1-160, 1-167, 1-168, 1-170, 1-172, 1-173, 1-175, 1-176, 1-183, 1-187 4. 1-185, 1-186, 1-187, 1-188, 1-189, 1-191, 1-192, 1-193, 1-194, 1-195, 1-196, 1-197, 1-198, 1-199, 1-200, 1-203, 1-204, 1-205, 1-206, 1-207, 1-212, 1-214, 1-215, 1-216, 1-218, 1-221, 1-222, 1-227, 1-229, 1-230, 1-233, 1-235, 1-236, 1-237, 1-238, 1-239, 1-240, 1-241, 1-243, 1-244, 1- 245, 1-246, 1-247, 1-248, 1-249, 1-250, 1-251, 1-254, 1-256, 1-257, 1-258, 1-259, 1-260, 1-263, 1-264, 1-275, 1-276, 1-277, 1-278, 1-279, 1-280, 1-281, 1-282, 1-283, 1-284, 1-285, 1-286, 1-287, 1-288, 1-289, 1-290, 1-291, 1-292, 1-293, 1-294, 1-295, 1-296, 1-297, 1-298, 1-299, 1-300,The compounds of 1-301, 1-302, 1-303, 1-304, 1-305, 1-310, 1-311, 1-312, 1-314, 1-315, 1-316, 2-3, 2-4, 2-5, 2-6, 2-7, 2-8, 2-9, 2-10, 2-11, 2-12, 2-16, 2-18, 2-19, 2-20 and 3-2 showed excellent activity against western flower thrips in the A judgment.

[0574] Industrial Applicability

[0575] The compound of the present invention or a salt thereof has excellent effects as an agricultural and horticultural insecticide.

Claims

1. A compound represented by the following general formula (1) or a salt thereof, General formula (1) [Chemical formula 1] In the formula, R 1 represents (a1) a hydrogen atom, R 2 represents (b1) an aromatic hydrocarbon group having 6 to 10 carbon atoms; (b2) an aromatic hydrocarbon group having 6 to 10 carbon atoms having one or more substituents independently selected from the substituent group A on the ring; (b3) a 5- or 6-membered monocyclic aromatic heterocyclic group containing 1 to 4 heteroatoms selected from oxygen atoms, sulfur atoms and nitrogen atoms as ring-constituting atoms in addition to carbon atoms, or an aromatic fused heterocyclic group in which the monocyclic aromatic heterocyclic ring is fused with a benzene ring or a monocyclic aromatic ring; or (b4) the monocyclic aromatic heterocyclic group or the aromatic fused heterocyclic group having one or more substituents independently selected from the substituent group A on the ring, in, R 2 In the tetrahydropyridazine ring, the atoms adjacent to the atoms bonded to the tetrahydropyridazine ring are unsubstituted C1-C6 alkylsulfonyl, halogenated C1-C6 alkylsulfonyl, N-C1-C6 alkylaminosulfonyl, N,N-diC1-C6 alkylaminosulfonyl and R 6 -(R 7 -N=)O=S group, where R 6 represents a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a halogenated C1-C6 alkyl group or a C1-C6 alkoxy C1-C6 alkyl group, R 7 represents a hydrogen atom, a cyano group, a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a halogenated C1-C6 alkyl group, a C2-C6 alkylcarbonyl group or a halogenated C2-C6 alkylcarbonyl group, R 3 represents (c1) a hydrogen atom; or (c2) a C1-C6 alkyl group, R 4 represents (d1) C1-C6 alkyl; (d2) C2-C6 alkenyl; (d3) C2-C6 alkynyl; (d4) C3-C6 cycloalkyl; (d5) halogenated C1-C6 alkyl; (d6) halogenated C2-C6 alkenyl; (d7) halogenated C2-C6 alkynyl; (d8) substituted C1-C6 alkyl having 1 to 3 substituents independently selected from substituent group B; (d9) substituted C3-C6 cycloalkyl having 1 to 3 substituents independently selected from substituent group C on the ring; (d10) C1-C6 alkylsulfonyl; (d11) N-C1-C6 alkylaminosulfonyl; (d12) phenyl; (d13) substituted C1-C6 alkyl having 1 to 5 substituents independently selected from substituent group D on the ring (d14) phenyl C1-C6 alkyl; (d15) substituted phenyl C1-C6 alkyl having 1 to 5 substituents independently selected from substituent group D on the ring; (d16) pyridyl; (d17) substituted pyridyl having 1 to 4 substituents independently selected from substituent group D on the ring; (d18) pyridazinyl; (d19) substituted pyridazinyl having 1 to 3 substituents independently selected from substituent group D on the ring; (d20) pyrimidinyl; (d21) substituted pyrimidinyl having 1 to 3 substituents independently selected from substituent group D on the ring; (d22) pyrazinyl; (d23) substituted pyrazine having 1 to 3 substituents independently selected from substituent group D on the ring (d24) pyrazolyl; (d25) substituted pyrazolyl having 1 to 3 substituents independently selected from the substituent group D on the ring; (d26) isoxazolyl; (d27) substituted isoxazolyl having 1 to 2 substituents independently selected from the substituent group D on the ring; (d28) isothiazolyl; (d29) substituted isothiazolyl having 1 to 2 substituents independently selected from the substituent group D on the ring; (d30) oxazolyl; (d31) substituted oxazolyl having 1 to 2 substituents independently selected from the substituent group D on the ring; (d32) thiazolyl; (d33) substituted thiazolyl having 1 to 2 substituents independently selected from the substituent group D on the ring; (d34) triazolyl; (d (d35) substituted triazolyl having 1 to 2 substituents independently selected from the substituent group D on the ring; (d36) thiadiazolyl; (d37) substituted thiadiazolyl having 1 substituent independently selected from the substituent group D on the ring; (d38) tetrazolyl; (d39) substituted tetrazolyl having 1 substituent independently selected from the substituent group D on the ring; (d40) triazinyl; (d41) substituted triazinyl having 1 to 2 substituents independently selected from the substituent group D on the ring; (d42) furanyl C1-C6 alkyl; (d43) substituted furanyl C1-C6 alkyl having 1 to 3 substituents independently selected from the substituent group D on the ring; (d44) thienyl C1-C6 alkyl;(d45) substituted thienyl C1-C6 alkyl having 1 to 3 substituents independently selected from the substituent group D on the ring; (d46) quinolyl; (d47) substituted quinolyl having 1 to 6 substituents independently selected from the substituent group D on the ring; (d48) benzothiazolyl; (d49) substituted benzothiazolyl having 1 to 4 substituents independently selected from the substituent group D on the ring; (d50) pyridyl C1-C6 alkyl; (d51) substituted thienyl C1-C6 alkyl having 1 to 3 substituents independently selected from the substituent group D on the ring; (d52) substituted pyridyl C1-C6 alkyl having 1 to 4 substituents on the ring; (d53) substituted pyrazinyl C1-C6 alkyl having 1 to 3 substituents independently selected from substituent group D on the ring; (d54) naphthyl; (d55) substituted naphthyl having 1 to 7 substituents independently selected from substituent group D on the ring; (d56) tetrahydronaphthyl; or (d57) substituted tetrahydronaphthyl having 1 to 10 substituents independently selected from substituent group D on the ring; X and Y each independently represent an oxygen atom or a sulfur atom, Substituent group A includes (e1) a halogen atom; (e2) a cyano group; (e3) a nitro group; (e4) a hydroxyl group; (e5) a carboxyl group; (e6) a C1-C6 alkyl group; (e7) a C2-C6 alkenyl group; (e8) a C2-C6 alkynyl group; (e9) a C1-C6 alkoxy group; (e10) a C3-C6 cycloalkyl group; (e11) a C1-C6 alkylthio group; (e12) a C1-C6 alkylsulfinyl group; (e13) a C1-C6 alkylsulfonyl group; (e14) a halogenated C1-C6 alkyl group; ( e15) halogenated C2-C6 alkenyl; (e16) halogenated C2-C6 alkynyl; (e17) halogenated C1-C6 alkoxy; (e18) halogenated C3-C6 cycloalkyl; (e19) halogenated C1-C6 alkylthio; (e20) halogenated C1-C6 alkylsulfinyl; (e21) halogenated C1-C6 alkylsulfonyl; (e22) C1-C6 alkylcarbonylamino; (e23) halogenated C1-C6 alkylcarbonylamino; (e24) C1-C6 alkylsulfonylamino; (e25) halogenated C1-C6 alkylcarbonylamino; (e26) halogenated C1-C6 alkylsulfonylamino; (e27) halogenated C1-C6 alkylcarbonylamino; (e28) halogenated C1-C6 alkylcarbonylamino; (e29) halogenated C1-C6 alkylsulfonylamino; (e30) halogenated C1-C6 alkylsulfonylamino; (e31) halogenated C1-C6 alkylsulfonylamino; (e32) halogenated C1-C6 alkylcarbonylamino; (e33) halogenated C1-C6 alkylcarbonylamino; (e34) halogenated C1-C6 alkylsulfonylamino; (e35) halogenated C1-C6 alkylcarbonylamino; (e36) halogenated C1-C6 alkylcarbonylamino; (e37) halogenated C1-C6 alkylcarbonylamino; (e38) halogenated C1-C6 alkylcarbonylamino; (e39) halogenated C1-C6 alkylcarbonylamino; (e40) halogenated C1-C6 alkylsulfonylamino; ( (e25) halogenated C1-C6 alkylsulfonylamino; (e26) SF5 group; (e27) C1-C6 alkoxy C1-C6 alkyl; (e28) N-C1-C6 alkylcarboxamide; (e29) N-halogenated C1-C6 alkylcarboxamide; (e30) oxadiazolyl; (e31) having on the ring independently selected from halogen atoms, cyano, C1-C6 alkyl, C1-C6 alkoxy, C3-C6 cycloalkyl, C1-C6 alkylthio, C1-C6 alkylsulfinyl, substituted oxadiazolyl with one substituent selected from C1-C6 alkylsulfonyl, halogenated C1-C6 alkyl and halogenated C1-C6 alkoxy; (e32) C1-C6 alkoxycarbonyl; (e33) methylenedioxy optionally substituted with one to two substituents selected from halogen atoms, phenyl and C1-C6 alkyl, formed by two adjacent substituents; (e34) N-C1-C6 alkylaminosulfonyl; (e35) N,N-di-C1-C6 alkylaminosulfonyl; (e36) R 6 -(R 7 -N=)O=S group, where R 6 represents a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a halogenated C1-C6 alkyl group or a C1-C6 alkoxy C1-C6 alkyl group, R 7 represents a hydrogen atom, a cyano group, a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a halogenated C1-C6 alkyl group, a C2-C6 alkylcarbonyl group or a halogenated C2-C6 alkylcarbonyl group; and (e37) a substituted C3-C6 cycloalkyl group having 1 to 3 substituents independently selected from a halogen atom, a cyano group, a C1-C6 alkyl group, a C1-C6 alkoxy group and a C1-C6 alkylcarbonyl group on the ring, Substituent Group B comprises (f1) cyano; (f2) C3-C6 cycloalkyl; (f3) C1-C6 alkoxy; (f4) C1-C6 alkylthio; (f5) C1-C6 alkylsulfinyl; (f6) C1-C6 alkylsulfonyl; (f7) halogenated C3-C6 cycloalkyl; (f8) halogenated C1-C6 alkoxy; (f9) halogenated C1-C6 alkylthio; (f10) halogenated C1-C6 alkylsulfinyl; (f11) halogenated C1-C6 alkylsulfonyl; (f12) carboxamide; and (f13) phenylcarbonyl, Substituent Group C comprises (g1) cyano; (g2) C1-C6 alkyl; (g3) C3-C6 cycloalkyl; (g4) C1-C6 alkoxy; (g5) C1-C6 alkylthio; (g6) C1-C6 alkylsulfinyl; (g7) C1-C6 alkylsulfonyl; (g8) halogenated C3-C6 cycloalkyl; (g9) halogenated C1-C6 alkoxy; (g10) halogenated C1-C6 alkylthio; (g11) halogenated C1-C6 alkylsulfinyl; (g12) halogenated C1-C6 alkylsulfonyl; (g13) halogenated C1-C6 alkyl; (g14) carboxamide; (g15) C2-C6 alkynyl; and (g16) phenyl, The substituent group D includes (h1) a halogen atom; (h2) a cyano group; (h3) a hydroxyl group; (h4) a carboxyl group; (h5) a C1-C6 alkyl group; (h6) a C1-C6 alkoxy group; (h7) a C3-C6 cycloalkyl group; (h8) a C1-C6 alkylthio group; (h9) a C1-C6 alkylsulfinyl group; (h10) a C1-C6 alkylsulfonyl group; (h11) a halogenated C1-C6 alkyl group; (h12) a halogenated C1-C6 alkoxy group; (h13) a halogenated C3-C6 cycloalkyl group; (h14) a halogenated C1-C6 alkylthio group (h15) halogenated C1-C6 alkylsulfinyl; (h16) halogenated C1-C6 alkylsulfonyl; (h17) C1-C6 alkoxycarbonyl; (h18) N-C1-C6 alkylcarboxamide; (h19) N-halogenated C1-C6 alkylcarboxamide; (h20) a methylenedioxy group obtained by combining two adjacent substituents and optionally substituted with 1 to 2 substituents selected from a halogen atom, a phenyl group and a C1-C6 alkyl group; (h21) a nitro group; (h22) an amino group; and (h23) a benzyloxycarbonyl group.

2. The compound or salt thereof according to claim 1, wherein R 1 , R 3 , R 4 , X, Y, substituent groups A, B, C and D are the same as those in claim 1, R 2 (b5) phenyl; (b6) substituted phenyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b7) pyridyl; (b8) substituted pyridyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b9) pyridazinyl; (b10) substituted pyridazinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b11) pyrimidinyl; (b12) substituted pyrimidinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b13) pyrazinyl; (b14) substituted pyrazinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b15) furanyl; (b16) (b17) substituted furanyl having 1 to 3 substituents from Substituent Group A; (b18) substituted thienyl having 1 to 3 substituents independently selected from Substituent Group A on the ring; (b19) isoxazolyl; (b20) substituted isoxazolyl having 1 to 2 substituents independently selected from Substituent Group A on the ring; (b21) oxazolyl; (b22) substituted oxazolyl having 1 to 2 substituents independently selected from Substituent Group A on the ring; (b23) pyrazolyl; (b24) substituted pyrazolyl having 1 to 3 substituents independently selected from Substituent Group A on the ring; (b25) imidazolyl; (b26) substituted imidazole having 1 to 3 substituents independently selected from Substituent Group A on the ring (b27) triazolyl; (b28) substituted triazolyl having 1 to 2 substituents independently selected from the substituent group A on the ring; (b29) thiazolyl; (b30) substituted thiazolyl having 1 to 2 substituents independently selected from the substituent group A on the ring; (b31) isothiazolyl; (b32) substituted isothiazolyl having 1 to 2 substituents independently selected from the substituent group A on the ring; (b33) thiadiazolyl; (b34) substituted thiadiazolyl having 1 substituent independently selected from the substituent group A on the ring; (b35) imidazopyridinyl; (b36) substituted imidazopyridinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b37) quinoxalinyl ; (b38) substituted quinoxalinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b39) benzoxazolyl; (b40) substituted benzoxazolyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b41) benzimidazolyl; (b42) substituted benzimidazolyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b43) benzothiazolyl; (b44) substituted benzothiazolyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b45) thiazolopyridinyl; (b46) substituted thiazolopyridinyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b47) quinolyl;(b48) substituted quinolyl having 1 to 6 substituents independently selected from the substituent group A on the ring; (b49) naphthyl; (b50) substituted naphthyl having 1 to 7 substituents independently selected from the substituent group A on the ring; (b51) triazine; (b52) substituted triazine having 1 to 2 substituents independently selected from the substituent group A on the ring; (b53) pyrrolyl; (b54) substituted pyrrolyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b55) tetrazolyl; (b56) substituted tetrazolyl having 1 substituent independently selected from the substituent group A on the ring; (b57) oxadiazolyl; (b58) 1 substituent independently selected from the substituent group A on the ring (b59) 2-oxopyridyl; (b60) substituted 2-oxopyridyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b61) benzofuranyl; (b62) substituted benzofuranyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b63) benzisoxazolyl; (b64) substituted benzisoxazolyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b65) benzothienyl; (b66) substituted benzothienyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b67) benzisothiazolyl; (b68) substituted 1 to 4 substituents independently selected from the substituent group A on the ring (b69) indolyl; (b70) substituted indolyl having 1 to 6 substituents independently selected from substituent group A on the ring; (b71) isoindolyl; (b72) substituted isoindolyl having 1 to 6 substituents independently selected from substituent group A on the ring; (b73) indazolyl; (b74) substituted indazolyl having 1 to 5 substituents independently selected from substituent group A on the ring; (b75) benzotriazolyl; (b76) substituted benzotriazolyl having 1 to 4 substituents independently selected from substituent group A on the ring; (b77) furanopyridinyl; (b78) substituted furanopyridinyl having 1 to 4 substituents independently selected from substituent group A on the ring; b79) thienopyridinyl; (b80) substituted thienopyridinyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b81) indolizinyl; (b82) substituted indolizinyl having 1 to 6 substituents independently selected from the substituent group A on the ring; (b83) pyrrolopyridinyl; (b84) substituted pyrrolopyridinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b85) pyrrolopyrimidinyl; (b86) substituted pyrrolopyrimidinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b87) oxazolopyridinyl; (b88) substituted oxazolopyridinyl having 1 to 3 substituents independently selected from the substituent group A on the ring;(b89) isoxazolopyridinyl; (b90) substituted isoxazolopyridinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b91) isothiazolopyridinyl; (b92) substituted isothiazolopyridinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b93) imidazopyrimidinyl; (b94) substituted imidazopyrimidinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b95) pyrazolopyridinyl; (b96) substituted pyrazolopyridinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b97) pyrazolopyrimidinyl; (b98) substituted pyrazolopyrimidinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b99) triazolopyridinyl; (b100) substituted pyrazolopyridinyl having 1 to 4 substituents independently selected from the substituent group A on the ring Substituted triazolopyridinyl; (b101) triazolopyrimidinyl; (b102) substituted triazolopyrimidinyl having 1 to 4 substituents independently selected from substituent group A on the ring; (b103) isoquinolyl; (b104) substituted isoquinolyl having 1 to 6 substituents independently selected from substituent group A on the ring; (b105) oxazinyl; (b106) substituted triazolopyrimidinyl having 1 to 5 substituents independently selected from substituent group A on the ring substituted oxazinyl; (b107) phthalazinyl; (b108) substituted phthalazinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b109) quinazolinyl; (b110) substituted quinazolinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b111) naphthyridinyl; or (b112) substituted naphthyridinyl having 1 to 5 substituents independently selected from the substituent group A on the ring. ; 3. The compound or salt thereof according to claim 1 or 2, wherein R 1 is (a1) a hydrogen atom, R 2 (b5) phenyl; (b6) substituted phenyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b7) pyridyl; (b8) substituted pyridyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b9) pyridazinyl; (b10) substituted pyridazinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b11) pyrimidinyl; (b12) substituted pyrimidinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b13) pyrazinyl; (b14) substituted pyrazinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b15) furanyl; (b16) (b17) substituted furanyl having 1 to 3 substituents from Substituent Group A; (b18) substituted thienyl having 1 to 3 substituents independently selected from Substituent Group A on the ring; (b19) isoxazolyl; (b20) substituted isoxazolyl having 1 to 2 substituents independently selected from Substituent Group A on the ring; (b21) oxazolyl; (b22) substituted oxazolyl having 1 to 2 substituents independently selected from Substituent Group A on the ring; (b23) pyrazolyl; (b24) substituted pyrazolyl having 1 to 3 substituents independently selected from Substituent Group A on the ring; (b25) imidazolyl; (b26) substituted imidazole having 1 to 3 substituents independently selected from Substituent Group A on the ring (b27) triazolyl; (b28) substituted triazolyl having 1 to 2 substituents independently selected from the substituent group A on the ring; (b29) thiazolyl; (b30) substituted thiazolyl having 1 to 2 substituents independently selected from the substituent group A on the ring; (b31) isothiazolyl; (b32) substituted isothiazolyl having 1 to 2 substituents independently selected from the substituent group A on the ring; (b33) thiadiazolyl; (b34) substituted thiadiazolyl having 1 substituent independently selected from the substituent group A on the ring; (b35) imidazopyridinyl; (b36) substituted imidazopyridinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b37) quinoxalinyl ; (b38) substituted quinoxalinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b39) benzoxazolyl; (b40) substituted benzoxazolyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b41) benzimidazolyl; (b42) substituted benzimidazolyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b43) benzothiazolyl; (b44) substituted benzothiazolyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b45) thiazolopyridinyl; (b46) substituted thiazolopyridinyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b47) quinolyl;or (b48) a substituted quinolyl group having 1 to 6 substituents independently selected from Substituent Group A on the ring; R 3 is (c1) a hydrogen atom; or (c2) a C1-C6 alkyl group, R 4 (d1) C1-C6 alkyl; (d2) C2-C6 alkenyl; (d3) C2-C6 alkynyl; (d4) C3-C6 cycloalkyl; (d5) halogenated C1-C6 alkyl; (d8) substituted C1-C6 alkyl having 1 to 3 substituents independently selected from substituent group B; (d9) substituted C3-C6 cycloalkyl having 1 to 3 substituents independently selected from substituent group C on the ring; (d10) C1-C6 alkylsulfonyl; (d11) N-C1-C6 alkylaminosulfonyl; (d12) phenyl; (d13) substituted phenyl having 1 to 5 substituents independently selected from substituent group D on the ring; (d14) phenyl C1-C6 alkyl; (d15) substituted C1-C6 alkyl having 1 to 5 substituents independently selected from substituent group D on the ring; (d16) pyridyl; (d17) substituted pyridyl having 1 to 4 substituents independently selected from substituent group D on the ring; (d18) pyridazinyl; (d19) substituted pyridazinyl having 1 to 3 substituents independently selected from substituent group D on the ring; (d20) pyrimidinyl; (d21) substituted pyrimidinyl having 1 to 3 substituents independently selected from substituent group D on the ring; (d22) pyrazinyl; (d23) substituted pyrazinyl having 1 to 3 substituents independently selected from substituent group D on the ring; (d24) pyrazolyl; (d25) substituted pyridazinyl having 1 to 3 substituents independently selected from substituent group D on the ring Substituted pyrazolyl; (d26) isoxazolyl; (d27) substituted isoxazolyl having 1 to 2 substituents independently selected from the substituent group D on the ring; (d28) isothiazolyl; (d29) substituted isothiazolyl having 1 to 2 substituents independently selected from the substituent group D on the ring; (d30) oxazolyl; (d31) substituted oxazolyl having 1 to 2 substituents independently selected from the substituent group D on the ring; (d32) thiazolyl; (d33) substituted thiazolyl having 1 to 2 substituents independently selected from the substituent group D on the ring; (d34) triazolyl; (d35) substituted triazolyl having 1 to 2 substituents independently selected from the substituent group D on the ring; (d36) thiadiazolyl; (d (d37) substituted thiadiazolyl having one substituent independently selected from the substituent group D on the ring; (d38) tetrazolyl; (d39) substituted tetrazolyl having one substituent independently selected from the substituent group D on the ring; (d40) triazinyl; (d41) substituted triazinyl having 1 to 2 substituents independently selected from the substituent group D on the ring; (d42) furanyl C1-C6 alkyl; (d43) substituted furanyl C1-C6 alkyl having 1 to 3 substituents independently selected from the substituent group D on the ring; (d44) thienyl C1-C6 alkyl; (d45) substituted thienyl C1-C6 alkyl having 1 to 3 substituents independently selected from the substituent group D on the ring; (d46) quinolyl;(d47) substituted quinolyl having 1 to 6 substituents independently selected from the substituent group D on the ring; (d48) benzothiazolyl; (d49) substituted benzothiazolyl having 1 to 4 substituents independently selected from the substituent group D on the ring; (d50) pyridyl C1-C6 alkyl; (d51) substituted pyridyl C1-C6 alkyl having 1 to 4 substituents independently selected from the substituent group D on the ring; (d52 ) pyrazinyl C1-C6 alkyl; (d53) substituted pyrazinyl C1-C6 alkyl having 1 to 3 substituents independently selected from substituent group D on the ring; (d54) naphthyl; (d55) substituted naphthyl having 1 to 7 substituents independently selected from substituent group D on the ring; (d56) tetrahydronaphthyl; or (d57) substituted tetrahydronaphthyl having 1 to 10 substituents independently selected from substituent group D on the ring; Substituent group A includes (e1) a halogen atom; (e2) a cyano group; (e4) a hydroxyl group; (e5) a carboxyl group; (e6) a C1-C6 alkyl group; (e9) a C1-C6 alkoxy group; (e10) a C3-C6 cycloalkyl group; (e11) a C1-C6 alkylthio group; (e12) a C1-C6 alkylsulfinyl group; (e13) a C1-C6 alkylsulfonyl group; (e14) a halogenated C1-C6 alkyl group -C6 alkyl; (e17) halogenated C1-C6 alkoxy; (e18) halogenated C3-C6 cycloalkyl; (e19) halogenated C1-C6 alkylthio; (e20) halogenated C1-C6 alkylsulfinyl; (e21) halogenated C1-C6 alkylsulfonyl; (e22) C1-C6 alkylcarbonylamino; (e24) C1-C6 alkylsulfonylamino; (e28) N -C1-C6 alkylcarboxamide; (e30) oxadiazolyl; (e31) a substituted oxadiazolyl having on the ring one substituent independently selected from a halogen atom, a cyano group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a C3-C6 cycloalkyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a halogenated C1-C6 alkyl group and a halogenated C1-C6 alkoxy group; (e32) a C1-C6 alkoxycarbonyl group; (e33) a methylenedioxy group optionally substituted with one or two substituents selected from a halogen atom, a phenyl group and a C1-C6 alkyl group; (e34) an N-C1-C6 alkylaminosulfonyl group; (e35) an N,N-diC1-C6 alkylaminosulfonyl group; (e36) R 6 -(R 7 -N=)O=S group, where R 6 represents a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a halogenated C1-C6 alkyl group or a C1-C6 alkoxy C1-C6 alkyl group, R 7 represents a hydrogen atom, a cyano group, a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a halogenated C1-C6 alkyl group, a C2-C6 alkylcarbonyl group or a halogenated C2-C6 alkylcarbonyl group; and (e37) a substituted C3-C6 cycloalkyl group having 1 to 3 substituents independently selected from a halogen atom, a cyano group, a C1-C6 alkyl group, a C1-C6 alkoxy group and a C1-C6 alkylcarbonyl group on the ring, Substituent Group B comprises (f1) cyano; (f2) C3-C6 cycloalkyl; (f3) C1-C6 alkoxy; (f4) C1-C6 alkylthio; (f5) C1-C6 alkylsulfinyl; (f6) C1-C6 alkylsulfonyl; (f7) halogenated C3-C6 cycloalkyl; (f8) halogenated C1-C6 alkoxy; (f9) halogenated C1-C6 alkylthio; (f10) halogenated C1-C6 alkylsulfinyl; and (f11) halogenated C1-C6 alkylsulfonyl, Substituent Group C comprises (g1) cyano; (g2) C1-C6 alkyl; (g3) C3-C6 cycloalkyl; (g4) C1-C6 alkoxy; (g5) C1-C6 alkylthio; (g6) C1-C6 alkylsulfinyl; (g7) C1-C6 alkylsulfonyl; (g8) halogenated C3-C6 cycloalkyl; (g9) halogenated C1-C6 alkoxy; (g10) halogenated C1-C6 alkylthio; (g11) halogenated C1-C6 alkylsulfinyl; (g12) halogenated C1-C6 alkylsulfonyl; (g13) halogenated C1-C6 alkyl; (g15) C2-C6 alkynyl; and (g16) phenyl, The substituent group D includes (h1) a halogen atom; (h2) a cyano group; (h3) a hydroxyl group; (h4) a carboxyl group; (h5) a C1-C6 alkyl group; (h6) a C1-C6 alkoxy group; (h7) a C3-C6 cycloalkyl group; (h8) a C1-C6 alkylthio group; (h9) a C1-C6 alkylsulfinyl group; (h10) a C1-C6 alkylsulfonyl group; (h11) a halogenated C1-C6 alkyl group; (h12) a halogenated C1-C6 alkoxy group; (h13) a halogenated C3-C6 cycloalkyl group; (h14 ) halogenated C1-C6 alkylthio; (h15) halogenated C1-C6 alkylsulfinyl; (h16) halogenated C1-C6 alkylsulfonyl; (h17) C1-C6 alkoxycarbonyl; (h18) N-C1-C6 alkylcarboxamide; (h20) a methylenedioxy group obtained by combining two adjacent substituents and optionally substituted with one or two substituents selected from a halogen atom, a phenyl group and a C1-C6 alkyl group; (h21) a nitro group; (h22) an amino group; and (h23) a benzyloxycarbonyl group.

4. The compound or salt thereof according to claim 1 or 2, wherein R 1 is (a1) a hydrogen atom, R 2 (b5) phenyl; (b6) substituted phenyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b7) pyridyl; (b8) substituted pyridyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b9) pyridazinyl; (b10) substituted pyridazinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b11) pyrimidinyl; (b12) substituted pyrimidinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b13) pyrazinyl; (b14) substituted pyrazinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b23) pyrazolyl; (b24) substituted pyrazolyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b27) triazolyl ; (b28) a substituted triazolyl group having 1 to 2 substituents independently selected from the substituent group A on the ring; (b29) a thiazolyl group; (b30) a substituted thiazolyl group having 1 to 2 substituents independently selected from the substituent group A on the ring; (b33) a thiadiazolyl group; (b34) a substituted thiadiazolyl group having 1 substituent independently selected from the substituent group A on the ring; (b43) a benzothiazolyl group; (b44) a substituted benzothiazolyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b45) a thiazolopyridyl group; (b46) a substituted thiazolopyridyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b47) a quinolyl group; or (b48) a substituted quinolyl group having 1 to 6 substituents independently selected from the substituent group A on the ring, R 3 is (c1) a hydrogen atom; or (c2) a C1-C6 alkyl group, R 4 (d1) C1-C6 alkyl; (d2) C2-C6 alkenyl; (d3) C2-C6 alkynyl; (d4) C3-C6 cycloalkyl; (d5) halogenated C1-C6 alkyl; (d8) substituted C1-C6 alkyl having 1 to 3 substituents independently selected from substituent group B; (d9) substituted C3-C6 cycloalkyl having 1 to 3 substituents independently selected from substituent group C on the ring; (d12) phenyl; (d13) substituted phenyl having 1 to 5 substituents independently selected from substituent group D on the ring; (d14) phenyl C1-C6 alkyl; (d15) substituted phenyl C1-C6 alkyl having 1 to 5 substituents independently selected from substituent group D on the ring; (d16) pyridyl ; (d17) substituted pyridyl having 1 to 4 substituents independently selected from the substituent group D on the ring; (d18) pyridazinyl; (d19) substituted pyridazinyl having 1 to 3 substituents independently selected from the substituent group D on the ring; (d20) pyrimidinyl; (d21) substituted pyrimidinyl having 1 to 3 substituents independently selected from the substituent group D on the ring; (d22) pyrazinyl; (d24) pyrazolyl; (d25) substituted pyrazolyl having 1 to 3 substituents independently selected from the substituent group D on the ring; (d26) isoxazolyl; (d27) substituted isoxazolyl having 1 to 2 substituents independently selected from the substituent group D on the ring; (d32) thiazolyl; (d33) substituted thiazolyl having 1 to 2 substituents independently selected from the substituent group D; (d34) triazolyl; (d35) substituted triazolyl having 1 to 2 substituents independently selected from the substituent group D on the ring; (d36) thiadiazolyl; (d37) substituted thiadiazolyl having 1 substituent independently selected from the substituent group D on the ring; (d42) furanyl C1-C6 alkyl; (d43) substituted furanyl C1-C6 alkyl having 1 to 3 substituents independently selected from the substituent group D on the ring; (d44) thienyl C1-C6 alkyl; (d45) substituted thienyl C1-C6 alkyl having 1 to 3 substituents independently selected from the substituent group D on the ring; (d46) quinolyl; (d47) (d48) substituted quinolyl having 1 to 6 substituents independently selected from the substituent group D on the ring; (d49) substituted benzothiazolyl having 1 to 4 substituents independently selected from the substituent group D on the ring; (d50) pyridyl C1-C6 alkyl; (d51) substituted pyridyl C1-C6 alkyl having 1 to 4 substituents independently selected from the substituent group D on the ring; (d52) pyrazinyl C1-C6 alkyl; (d53) substituted pyrazinyl C1-C6 alkyl having 1 to 3 substituents independently selected from the substituent group D on the ring; (d54) naphthyl; (d55) substituted naphthyl having 1 to 7 substituents independently selected from the substituent group D on the ring; (d56) tetrahydronaphthyl;or (d57) a substituted tetrahydronaphthyl group having 1 to 10 substituents independently selected from Substituent Group D on the ring; Substituent Group A comprises (e1) a halogen atom; (e2) a cyano group; (e6) a C1-C6 alkyl group; (e9) a C1-C6 alkoxy group; (e11) a C1-C6 alkylthio group; (e12) a C1-C6 alkylsulfinyl group; (e13) a C1-C6 alkylsulfonyl group; (e14) a halogenated C1-C6 alkyl group; (e17) a halogenated C1-C6 alkoxy group; (e19) a halogenated C1-C6 alkylthio group; (e21) a halogenated C1-C6 alkylsulfonyl group; (e32) a C1-C6 alkoxycarbonyl group; (e34) an N-C1-C6 alkylaminosulfonyl group; and (e35) an N,N-diC1-C6 alkylaminosulfonyl group. Substituent Group B comprises (f1) cyano; (f2) C3-C6 cycloalkyl; (f3) C1-C6 alkoxy; and (f4) C1-C6 alkylthio, Substituent group C comprises (g1) cyano; (g2) C1-C6 alkyl; (g13) halogenated C1-C6 alkyl; (g15) C2-C6 alkynyl; and (g16) phenyl, The substituent group D includes (h1) a halogen atom; (h2) a cyano group; (h3) a hydroxyl group; (h5) a C1-C6 alkyl group; (h6) a C1-C6 alkoxy group; (h8) a C1-C6 alkylthio group; (h11) a halogenated C1-C6 alkyl group; (h12) a halogenated C1-C6 alkoxy group; (h17) a C1-C6 alkoxycarbonyl group; (h20) a methylenedioxy group formed by two adjacent substituents, which is optionally substituted with one or two substituents selected from a halogen atom, a phenyl group and a C1-C6 alkyl group; and (h21) a nitro group.

5. An insecticide comprising the compound according to any one of claims 1 to 4 or a salt or N-oxide thereof as an active ingredient.

6. An agricultural and horticultural insecticide comprising the compound or its salt or N-oxide according to any one of claims 1 to 4 as an active ingredient.

7. An external parasite control agent for animals, comprising the compound or its salt or N-oxide according to any one of claims 1 to 4 as an active ingredient.

8. An agent for controlling internal parasites for animals, comprising the compound or its salt or N-oxide according to any one of claims 1 to 4 as an active ingredient.

9. A method of using an insecticide, wherein: Treat plants or soil with an effective amount of the pesticide according to claim 5 or 6.

10. Use of the compound according to any one of claims 1 to 4 or its salt or N-oxide as an insecticide.

11. A compound represented by the following general formula (13A) or a salt thereof, General formula (13A) [Chemical formula 2] In the formula, R 1 represents (a1) a hydrogen atom, R 2 represents (b1) an aromatic hydrocarbon group having 6 to 10 carbon atoms; (b2) an aromatic hydrocarbon group having 6 to 10 carbon atoms having one or more substituents independently selected from the substituent group A on the ring; (b3) a 5- or 6-membered monocyclic aromatic heterocyclic group containing 1 to 4 heteroatoms selected from oxygen atoms, sulfur atoms and nitrogen atoms as ring-constituting atoms in addition to carbon atoms, or an aromatic fused heterocyclic group in which the monocyclic aromatic heterocyclic ring is fused with a benzene ring or a monocyclic aromatic ring; or (b4) the monocyclic aromatic heterocyclic group or the aromatic fused heterocyclic group having one or more substituents independently selected from the substituent group A on the ring, in, R 2 In the tetrahydropyridazine ring, the atoms adjacent to the atoms bonded to the tetrahydropyridazine ring are unsubstituted C1-C6 alkylsulfonyl, halogenated C1-C6 alkylsulfonyl, N-C1-C6 alkylaminosulfonyl, N,N-diC1-C6 alkylaminosulfonyl and R 6 -(R 7 -N=)O=S group, where R 6 represents a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a halogenated C1-C6 alkyl group or a C1-C6 alkoxy C1-C6 alkyl group, R 7 represents a hydrogen atom, a cyano group, a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a halogenated C1-C6 alkyl group, a C2-C6 alkylcarbonyl group or a halogenated C2-C6 alkylcarbonyl group, Substituent group A includes (e1) a halogen atom; (e2) a cyano group; (e3) a nitro group; (e4) a hydroxyl group; (e5) a carboxyl group; (e6) a C1-C6 alkyl group; (e7) a C2-C6 alkenyl group; (e8) a C2-C6 alkynyl group; (e9) a C1-C6 alkoxy group; (e10) a C3-C6 cycloalkyl group; (e11) a C1-C6 alkylthio group; (e12) a C1-C6 alkylsulfinyl group; (e13) a C1-C6 alkylsulfonyl group; (e14) a halogenated C1-C6 alkyl group; ( e15) halogenated C2-C6 alkenyl; (e16) halogenated C2-C6 alkynyl; (e17) halogenated C1-C6 alkoxy; (e18) halogenated C3-C6 cycloalkyl; (e19) halogenated C1-C6 alkylthio; (e20) halogenated C1-C6 alkylsulfinyl; (e21) halogenated C1-C6 alkylsulfonyl; (e22) C1-C6 alkylcarbonylamino; (e23) halogenated C1-C6 alkylcarbonylamino; (e24) C1-C6 alkylsulfonylamino; (e25) halogenated C1-C6 alkylcarbonylamino; (e26) halogenated C1-C6 alkylsulfonylamino; (e27) halogenated C1-C6 alkylcarbonylamino; (e28) halogenated C1-C6 alkylcarbonylamino; (e29) halogenated C1-C6 alkylsulfonylamino; (e30) halogenated C1-C6 alkylsulfonylamino; (e31) halogenated C1-C6 alkylsulfonylamino; (e32) halogenated C1-C6 alkylcarbonylamino; (e33) halogenated C1-C6 alkylcarbonylamino; (e34) halogenated C1-C6 alkylsulfonylamino; (e35) halogenated C1-C6 alkylcarbonylamino; (e36) halogenated C1-C6 alkylcarbonylamino; (e37) halogenated C1-C6 alkylcarbonylamino; (e38) halogenated C1-C6 alkylcarbonylamino; (e39) halogenated C1-C6 alkylcarbonylamino; (e40) halogenated C1-C6 alkylsulfonylamino; ( (e25) halogenated C1-C6 alkylsulfonylamino; (e26) SF5 group; (e27) C1-C6 alkoxy C1-C6 alkyl; (e28) N-C1-C6 alkylcarboxamide; (e29) N-halogenated C1-C6 alkylcarboxamide; (e30) oxadiazolyl; (e31) having on the ring independently selected from halogen atoms, cyano, C1-C6 alkyl, C1-C6 alkoxy, C3-C6 cycloalkyl, C1-C6 alkylthio, C1-C6 alkylsulfinyl, substituted oxadiazolyl having one substituent selected from C1-C6 alkylsulfonyl, halogenated C1-C6 alkyl and halogenated C1-C6 alkoxy; (e32) C1-C6 alkoxycarbonyl; (e33) methylenedioxy optionally substituted with one or two substituents selected from halogen atoms, phenyl and C1-C6 alkyl, obtained by combining two adjacent substituents; (e34) N-C1-C6 alkylaminosulfonyl; (e35) N,N-di-C1-C6 alkylaminosulfonyl; (e36) R 6 -(R 7 -N=)O=S group, where R 6 represents a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a halogenated C1-C6 alkyl group or a C1-C6 alkoxy C1-C6 alkyl group, R 7 represents a hydrogen atom, a cyano group, a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a halogenated C1-C6 alkyl group, a C2-C6 alkylcarbonyl group or a halogenated C2-C6 alkylcarbonyl group; and (e37) a substituted C3-C6 cycloalkyl group having 1 to 3 substituents on the ring independently selected from a halogen atom, a cyano group, a C1-C6 alkyl group, a C1-C6 alkoxy group and a C1-C6 alkylcarbonyl group.

12. The compound or salt thereof according to claim 11, wherein R 1 and substituent group A is the same as in claim 11, R 2 (b5) phenyl; (b6) substituted phenyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b7) pyridyl; (b8) substituted pyridyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b9) pyridazinyl; (b10) substituted pyridazinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b11) pyrimidinyl; (b12) substituted pyrimidinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b13) pyrazinyl; (b14) substituted pyrazinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b15) furanyl; (b16) (b17) substituted furanyl having 1 to 3 substituents from Substituent Group A; (b18) substituted thienyl having 1 to 3 substituents independently selected from Substituent Group A on the ring; (b19) isoxazolyl; (b20) substituted isoxazolyl having 1 to 2 substituents independently selected from Substituent Group A on the ring; (b21) oxazolyl; (b22) substituted oxazolyl having 1 to 2 substituents independently selected from Substituent Group A on the ring; (b23) pyrazolyl; (b24) substituted pyrazolyl having 1 to 3 substituents independently selected from Substituent Group A on the ring; (b25) imidazolyl; (b26) substituted imidazole having 1 to 3 substituents independently selected from Substituent Group A on the ring (b27) triazolyl; (b28) substituted triazolyl having 1 to 2 substituents independently selected from the substituent group A on the ring; (b29) thiazolyl; (b30) substituted thiazolyl having 1 to 2 substituents independently selected from the substituent group A on the ring; (b31) isothiazolyl; (b32) substituted isothiazolyl having 1 to 2 substituents independently selected from the substituent group A on the ring; (b33) thiadiazolyl; (b34) substituted thiadiazolyl having 1 substituent independently selected from the substituent group A on the ring; (b35) imidazopyridinyl; (b36) substituted imidazopyridinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b37) quinoxalinyl ; (b38) substituted quinoxalinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b39) benzoxazolyl; (b40) substituted benzoxazolyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b41) benzimidazolyl; (b42) substituted benzimidazolyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b43) benzothiazolyl; (b44) substituted benzothiazolyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b45) thiazolopyridinyl; (b46) substituted thiazolopyridinyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b47) quinolyl;(b48) substituted quinolyl having 1 to 6 substituents independently selected from the substituent group A on the ring; (b49) naphthyl; (b50) substituted naphthyl having 1 to 7 substituents independently selected from the substituent group A on the ring; (b51) triazine; (b52) substituted triazine having 1 to 2 substituents independently selected from the substituent group A on the ring; (b53) pyrrolyl; (b54) substituted pyrrolyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b55) tetrazolyl; (b56) substituted tetrazolyl having 1 substituent independently selected from the substituent group A on the ring; (b57) oxadiazolyl; (b58) 1 substituent independently selected from the substituent group A on the ring (b59) 2-oxopyridyl; (b60) substituted 2-oxopyridyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b61) benzofuranyl; (b62) substituted benzofuranyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b63) benzisoxazolyl; (b64) substituted benzisoxazolyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b65) benzothienyl; (b66) substituted benzothienyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b67) benzisothiazolyl; (b68) substituted 1 to 4 substituents independently selected from the substituent group A on the ring (b69) indolyl; (b70) substituted indolyl having 1 to 6 substituents independently selected from substituent group A on the ring; (b71) isoindolyl; (b72) substituted isoindolyl having 1 to 6 substituents independently selected from substituent group A on the ring; (b73) indazolyl; (b74) substituted indazolyl having 1 to 5 substituents independently selected from substituent group A on the ring; (b75) benzotriazolyl; (b76) substituted benzotriazolyl having 1 to 4 substituents independently selected from substituent group A on the ring; (b77) furanopyridinyl; (b78) substituted furanopyridinyl having 1 to 4 substituents independently selected from substituent group A on the ring; b79) thienopyridinyl; (b80) substituted thienopyridinyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b81) indolizinyl; (b82) substituted indolizinyl having 1 to 6 substituents independently selected from the substituent group A on the ring; (b83) pyrrolopyridinyl; (b84) substituted pyrrolopyridinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b85) pyrrolopyrimidinyl; (b86) substituted pyrrolopyrimidinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b87) oxazolopyridinyl; (b88) substituted oxazolopyridinyl having 1 to 3 substituents independently selected from the substituent group A on the ring;(b89) isoxazolopyridinyl; (b90) substituted isoxazolopyridinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b91) isothiazolopyridinyl; (b92) substituted isothiazolopyridinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b93) imidazopyrimidinyl; (b94) substituted imidazopyrimidinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b95) pyrazolopyridinyl; (b96) substituted pyrazolopyridinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b97) pyrazolopyrimidinyl; (b98) substituted pyrazolopyrimidinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b99) triazolopyridinyl; (b100) substituted pyrazolopyridinyl having 1 to 4 substituents independently selected from the substituent group A on the ring Substituted triazolopyridinyl; (b101) triazolopyrimidinyl; (b102) substituted triazolopyrimidinyl having 1 to 4 substituents independently selected from substituent group A on the ring; (b103) isoquinolyl; (b104) substituted isoquinolyl having 1 to 6 substituents independently selected from substituent group A on the ring; (b105) oxazinyl; (b106) substituted triazolopyrimidinyl having 1 to 5 substituents independently selected from substituent group A on the ring substituted oxazinyl; (b107) phthalazinyl; (b108) substituted phthalazinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b109) quinazolinyl; (b110) substituted quinazolinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b111) naphthyridinyl; or (b112) substituted naphthyridinyl having 1 to 5 substituents independently selected from the substituent group A on the ring. ; 13. The compound or salt thereof according to claim 11 or 12, wherein R 1 is (a1) a hydrogen atom, R 2 (b5) phenyl; (b6) substituted phenyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b7) pyridyl; (b8) substituted pyridyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b9) pyridazinyl; (b10) substituted pyridazinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b11) pyrimidinyl; (b12) substituted pyrimidinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b13) pyrazinyl; (b14) substituted pyrazinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b15) furanyl; (b16) (b17) substituted furanyl having 1 to 3 substituents from Substituent Group A; (b18) substituted thienyl having 1 to 3 substituents independently selected from Substituent Group A on the ring; (b19) isoxazolyl; (b20) substituted isoxazolyl having 1 to 2 substituents independently selected from Substituent Group A on the ring; (b21) oxazolyl; (b22) substituted oxazolyl having 1 to 2 substituents independently selected from Substituent Group A on the ring; (b23) pyrazolyl; (b24) substituted pyrazolyl having 1 to 3 substituents independently selected from Substituent Group A on the ring; (b25) imidazolyl; (b26) substituted imidazole having 1 to 3 substituents independently selected from Substituent Group A on the ring (b27) triazolyl; (b28) substituted triazolyl having 1 to 2 substituents independently selected from the substituent group A on the ring; (b29) thiazolyl; (b30) substituted thiazolyl having 1 to 2 substituents independently selected from the substituent group A on the ring; (b31) isothiazolyl; (b32) substituted isothiazolyl having 1 to 2 substituents independently selected from the substituent group A on the ring; (b33) thiadiazolyl; (b34) substituted thiadiazolyl having 1 substituent independently selected from the substituent group A on the ring; (b35) imidazopyridinyl; (b36) substituted imidazopyridinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b37) quinoxalinyl ; (b38) substituted quinoxalinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b39) benzoxazolyl; (b40) substituted benzoxazolyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b41) benzimidazolyl; (b42) substituted benzimidazolyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b43) benzothiazolyl; (b44) substituted benzothiazolyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b45) thiazolopyridinyl; (b46) substituted thiazolopyridinyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b47) quinolyl;or (b48) a substituted quinolyl group having 1 to 6 substituents independently selected from Substituent Group A on the ring; Substituent group A includes (e1) a halogen atom; (e2) a cyano group; (e4) a hydroxyl group; (e5) a carboxyl group; (e6) a C1-C6 alkyl group; (e9) a C1-C6 alkoxy group; (e10) a C3-C6 cycloalkyl group; (e11) a C1-C6 alkylthio group; (e12) a C1-C6 alkylsulfinyl group; (e13) a C1-C6 alkylsulfonyl group; (e14) a halogenated C1-C6 alkyl group -C6 alkyl; (e17) halogenated C1-C6 alkoxy; (e18) halogenated C3-C6 cycloalkyl; (e19) halogenated C1-C6 alkylthio; (e20) halogenated C1-C6 alkylsulfinyl; (e21) halogenated C1-C6 alkylsulfonyl; (e22) C1-C6 alkylcarbonylamino; (e24) C1-C6 alkylsulfonylamino; (e28) N -C1-C6 alkylcarboxamide; (e30) oxadiazolyl; (e31) a substituted oxadiazolyl having on the ring one substituent independently selected from a halogen atom, a cyano group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a C3-C6 cycloalkyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a halogenated C1-C6 alkyl group and a halogenated C1-C6 alkoxy group; (e32) a C1-C6 alkoxycarbonyl group; (e33) a methylenedioxy group optionally substituted with one or two substituents selected from a halogen atom, a phenyl group and a C1-C6 alkyl group; (e34) an N-C1-C6 alkylaminosulfonyl group; (e35) an N,N-diC1-C6 alkylaminosulfonyl group; (e36) R 6 -(R 7 -N=)O=S group, where R 6 represents a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a halogenated C1-C6 alkyl group or a C1-C6 alkoxy C1-C6 alkyl group, R 7 represents a hydrogen atom, a cyano group, a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a halogenated C1-C6 alkyl group, a C2-C6 alkylcarbonyl group or a halogenated C2-C6 alkylcarbonyl group; and (e37) a substituted C3-C6 cycloalkyl group having 1 to 3 substituents on the ring independently selected from a halogen atom, a cyano group, a C1-C6 alkyl group, a C1-C6 alkoxy group and a C1-C6 alkylcarbonyl group.

14. The compound or salt thereof according to claim 11 or 12, wherein R 1 is (a1) a hydrogen atom, R 2 (b5) phenyl; (b6) substituted phenyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b7) pyridyl; (b8) substituted pyridyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b9) pyridazinyl; (b10) substituted pyridazinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b11) pyrimidinyl; (b12) substituted pyrimidinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b13) pyrazinyl; (b14) substituted pyrazinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b23) pyrazolyl; (b24) substituted pyrazolyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b27) triazolyl ; (b28) a substituted triazolyl group having 1 to 2 substituents independently selected from the substituent group A on the ring; (b29) a thiazolyl group; (b30) a substituted thiazolyl group having 1 to 2 substituents independently selected from the substituent group A on the ring; (b33) a thiadiazolyl group; (b34) a substituted thiadiazolyl group having 1 substituent independently selected from the substituent group A on the ring; (b43) a benzothiazolyl group; (b44) a substituted benzothiazolyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b45) a thiazolopyridyl group; (b46) a substituted thiazolopyridyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b47) a quinolyl group; or (b48) a substituted quinolyl group having 1 to 6 substituents independently selected from the substituent group A on the ring, Substituent group A includes (e1) a halogen atom; (e2) a cyano group; (e6) a C1-C6 alkyl group; (e9) a C1-C6 alkoxy group; (e11) a C1-C6 alkylthio group; (e12) a C1-C6 alkylsulfinyl group; (e13) a C1-C6 alkylsulfonyl group; (e14) a halogenated C1-C6 alkyl group; (e17) a halogenated C1-C6 alkoxy group; (e19) a halogenated C1-C6 alkylthio group; (e21) a halogenated C1-C6 alkylsulfonyl group; (e32) a C1-C6 alkoxycarbonyl group; (e34) an N-C1-C6 alkylaminosulfonyl group; and (e35) an N,N-diC1-C6 alkylaminosulfonyl group.

15. A compound represented by the following general formula (3A) or a salt thereof, General formula (3A) [Chemical formula 3] In the formula, R 1 represents (a1) a hydrogen atom, R 2 represents (b1) an aromatic hydrocarbon group having 6 to 10 carbon atoms; (b2) an aromatic hydrocarbon group having 6 to 10 carbon atoms having one or more substituents independently selected from the substituent group A on the ring; (b3) a 5- or 6-membered monocyclic aromatic heterocyclic group containing 1 to 4 heteroatoms selected from oxygen atoms, sulfur atoms and nitrogen atoms as ring-constituting atoms in addition to carbon atoms, or an aromatic fused heterocyclic group in which the monocyclic aromatic heterocyclic ring is fused with a benzene ring or a monocyclic aromatic ring; or (b4) the monocyclic aromatic heterocyclic group or the aromatic fused heterocyclic group having one or more substituents independently selected from the substituent group A on the ring, in, R 2 In the tetrahydropyridazine ring, the atoms adjacent to the atoms bonded to the tetrahydropyridazine ring are unsubstituted C1-C6 alkylsulfonyl, halogenated C1-C6 alkylsulfonyl, N-C1-C6 alkylaminosulfonyl, N,N-diC1-C6 alkylaminosulfonyl and R 6 -(R 7 -N=)O=S group, where R 6 represents a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a halogenated C1-C6 alkyl group or a C1-C6 alkoxy C1-C6 alkyl group, R 7 represents a hydrogen atom, a cyano group, a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a halogenated C1-C6 alkyl group, a C2-C6 alkylcarbonyl group or a halogenated C2-C6 alkylcarbonyl group, R 5 represents (i1) C1-C6 alkyl; or (i2) C1-C6 alkoxy C1-C6 alkyl, Substituent group A includes (e1) a halogen atom; (e2) a cyano group; (e3) a nitro group; (e4) a hydroxyl group; (e5) a carboxyl group; (e6) a C1-C6 alkyl group; (e7) a C2-C6 alkenyl group; (e8) a C2-C6 alkynyl group; (e9) a C1-C6 alkoxy group; (e10) a C3-C6 cycloalkyl group; (e11) a C1-C6 alkylthio group; (e12) a C1-C6 alkylsulfinyl group; (e13) a C1-C6 alkylsulfonyl group; (e14) a halogenated C1-C6 alkyl group; ( e15) halogenated C2-C6 alkenyl; (e16) halogenated C2-C6 alkynyl; (e17) halogenated C1-C6 alkoxy; (e18) halogenated C3-C6 cycloalkyl; (e19) halogenated C1-C6 alkylthio; (e20) halogenated C1-C6 alkylsulfinyl; (e21) halogenated C1-C6 alkylsulfonyl; (e22) C1-C6 alkylcarbonylamino; (e23) halogenated C1-C6 alkylcarbonylamino; (e24) C1-C6 alkylsulfonylamino; (e25) halogenated C1-C6 alkylcarbonylamino; (e26) halogenated C1-C6 alkylsulfonylamino; (e27) halogenated C1-C6 alkylcarbonylamino; (e28) halogenated C1-C6 alkylcarbonylamino; (e29) halogenated C1-C6 alkylsulfonylamino; (e30) halogenated C1-C6 alkylsulfonylamino; (e31) halogenated C1-C6 alkylsulfonylamino; (e32) halogenated C1-C6 alkylcarbonylamino; (e33) halogenated C1-C6 alkylcarbonylamino; (e34) halogenated C1-C6 alkylsulfonylamino; (e35) halogenated C1-C6 alkylcarbonylamino; (e36) halogenated C1-C6 alkylcarbonylamino; (e37) halogenated C1-C6 alkylcarbonylamino; (e38) halogenated C1-C6 alkylcarbonylamino; (e39) halogenated C1-C6 alkylcarbonylamino; (e40) halogenated C1-C6 alkylsulfonylamino; ( (e25) halogenated C1-C6 alkylsulfonylamino; (e26) SF5 group; (e27) C1-C6 alkoxy C1-C6 alkyl; (e28) N-C1-C6 alkylcarboxamide; (e29) N-halogenated C1-C6 alkylcarboxamide; (e30) oxadiazolyl; (e31) having on the ring independently selected from halogen atoms, cyano, C1-C6 alkyl, C1-C6 alkoxy, C3-C6 cycloalkyl, C1-C6 alkylthio, C1-C6 alkylsulfinyl, substituted oxadiazolyl having one substituent selected from C1-C6 alkylsulfonyl, halogenated C1-C6 alkyl and halogenated C1-C6 alkoxy; (e32) C1-C6 alkoxycarbonyl; (e33) methylenedioxy optionally substituted with one or two substituents selected from halogen atoms, phenyl and C1-C6 alkyl, obtained by combining two adjacent substituents; (e34) N-C1-C6 alkylaminosulfonyl; (e35) N,N-di-C1-C6 alkylaminosulfonyl; (e36) R 6 -(R 7 -N=)O=S group, where R 6 represents a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a halogenated C1-C6 alkyl group or a C1-C6 alkoxy C1-C6 alkyl group, R 7 represents a hydrogen atom, a cyano group, a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a halogenated C1-C6 alkyl group, a C2-C6 alkylcarbonyl group or a halogenated C2-C6 alkylcarbonyl group; and (e37) a substituted C3-C6 cycloalkyl group having 1 to 3 substituents on the ring independently selected from a halogen atom, a cyano group, a C1-C6 alkyl group, a C1-C6 alkoxy group and a C1-C6 alkylcarbonyl group.

16. The compound or salt thereof according to claim 15, wherein R 1 , R 5 and Substituent Group A is the same as in claim 15, R 2 (b5) phenyl; (b6) substituted phenyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b7) pyridyl; (b8) substituted pyridyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b9) pyridazinyl; (b10) substituted pyridazinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b11) pyrimidinyl; (b12) substituted pyrimidinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b13) pyrazinyl; (b14) substituted pyrazinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b15) furanyl; (b16) (b17) substituted furanyl having 1 to 3 substituents from Substituent Group A; (b18) substituted thienyl having 1 to 3 substituents independently selected from Substituent Group A on the ring; (b19) isoxazolyl; (b20) substituted isoxazolyl having 1 to 2 substituents independently selected from Substituent Group A on the ring; (b21) oxazolyl; (b22) substituted oxazolyl having 1 to 2 substituents independently selected from Substituent Group A on the ring; (b23) pyrazolyl; (b24) substituted pyrazolyl having 1 to 3 substituents independently selected from Substituent Group A on the ring; (b25) imidazolyl; (b26) substituted imidazolyl having 1 to 3 substituents independently selected from Substituent Group A on the ring Azolyl; (b27) triazolyl; (b28) substituted triazolyl having 1 to 2 substituents independently selected from the substituent group A on the ring; (b29) thiazolyl; (b30) substituted thiazolyl having 1 to 2 substituents independently selected from the substituent group A on the ring; (b31) isothiazolyl; (b32) substituted isothiazolyl having 1 to 2 substituents independently selected from the substituent group A on the ring; (b33) thiadiazolyl; (b34) substituted thiadiazolyl having 1 substituent independently selected from the substituent group A on the ring; (b35) imidazopyridinyl; (b36) substituted imidazopyridinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b37) quinoxaline (b38) substituted quinoxalinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b39) benzoxazolyl; (b40) substituted benzoxazolyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b41) benzimidazolyl; (b42) substituted benzimidazolyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b43) benzothiazolyl; (b44) substituted benzothiazolyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b45) thiazolopyridinyl; (b46) thiazolopyridinyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b47) quinolyl;(b48) substituted quinolyl having 1 to 6 substituents independently selected from the substituent group A on the ring; (b49) naphthyl; (b50) substituted naphthyl having 1 to 7 substituents independently selected from the substituent group A on the ring; (b51) triazine; (b52) substituted triazine having 1 to 2 substituents independently selected from the substituent group A on the ring; (b53) pyrrolyl; (b54) substituted pyrrolyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b55) tetrazolyl; (b56) substituted tetrazolyl having 1 substituent independently selected from the substituent group A on the ring; (b57) oxadiazolyl; (b58) 1 substituent independently selected from the substituent group A on the ring (b59) 2-oxopyridyl; (b60) substituted 2-oxopyridyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b61) benzofuranyl; (b62) substituted benzofuranyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b63) benzisoxazolyl; (b64) substituted benzisoxazolyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b65) benzothienyl; (b66) substituted benzothienyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b67) benzisothiazolyl; (b68) substituted 1 to 4 substituents independently selected from the substituent group A on the ring (b69) indolyl; (b70) substituted indolyl having 1 to 6 substituents independently selected from substituent group A on the ring; (b71) isoindolyl; (b72) substituted isoindolyl having 1 to 6 substituents independently selected from substituent group A on the ring; (b73) indazolyl; (b74) substituted indazolyl having 1 to 5 substituents independently selected from substituent group A on the ring; (b75) benzotriazolyl; (b76) substituted benzotriazolyl having 1 to 4 substituents independently selected from substituent group A on the ring; (b77) furanopyridinyl; (b78) substituted furanopyridinyl having 1 to 4 substituents independently selected from substituent group A on the ring; b79) thienopyridinyl; (b80) substituted thienopyridinyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b81) indolizinyl; (b82) substituted indolizinyl having 1 to 6 substituents independently selected from the substituent group A on the ring; (b83) pyrrolopyridinyl; (b84) substituted pyrrolopyridinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b85) pyrrolopyrimidinyl; (b86) substituted pyrrolopyrimidinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b87) oxazolopyridinyl; (b88) substituted oxazolopyridinyl having 1 to 3 substituents independently selected from the substituent group A on the ring;(b89) isoxazolopyridinyl; (b90) substituted isoxazolopyridinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b91) isothiazolopyridinyl; (b92) substituted isothiazolopyridinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b93) imidazopyrimidinyl; (b94) substituted imidazopyrimidinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b95) pyrazolopyridinyl; (b96) substituted pyrazolopyridinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b97) pyrazolopyrimidinyl; (b98) substituted pyrazolopyrimidinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b99) triazolopyridinyl; (b100) substituted pyrazolopyridinyl having 1 to 4 substituents independently selected from the substituent group A on the ring Substituted triazolopyridinyl; (b101) triazolopyrimidinyl; (b102) substituted triazolopyrimidinyl having 1 to 4 substituents independently selected from substituent group A on the ring; (b103) isoquinolyl; (b104) substituted isoquinolyl having 1 to 6 substituents independently selected from substituent group A on the ring; (b105) oxazinyl; (b106) substituted triazolopyrimidinyl having 1 to 5 substituents independently selected from substituent group A on the ring substituted oxazinyl; (b107) phthalazinyl; (b108) substituted phthalazinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b109) quinazolinyl; (b110) substituted quinazolinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b111) naphthyridinyl; or (b112) substituted naphthyridinyl having 1 to 5 substituents independently selected from the substituent group A on the ring. ; 17. The compound or salt thereof according to claim 15 or 16, wherein R 1 is (a1) a hydrogen atom, R 2 (b5) phenyl; (b6) substituted phenyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b7) pyridyl; (b8) substituted pyridyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b9) pyridazinyl; (b10) substituted pyridazinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b11) pyrimidinyl; (b12) substituted pyrimidinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b13) pyrazinyl; (b14) substituted pyrazinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b15) furanyl; (b16) (b17) substituted furanyl having 1 to 3 substituents from Substituent Group A; (b18) substituted thienyl having 1 to 3 substituents independently selected from Substituent Group A on the ring; (b19) isoxazolyl; (b20) substituted isoxazolyl having 1 to 2 substituents independently selected from Substituent Group A on the ring; (b21) oxazolyl; (b22) substituted oxazolyl having 1 to 2 substituents independently selected from Substituent Group A on the ring; (b23) pyrazolyl; (b24) substituted pyrazolyl having 1 to 3 substituents independently selected from Substituent Group A on the ring; (b25) imidazolyl; (b26) substituted imidazole having 1 to 3 substituents independently selected from Substituent Group A on the ring (b27) triazolyl; (b28) substituted triazolyl having 1 to 2 substituents independently selected from the substituent group A on the ring; (b29) thiazolyl; (b30) substituted thiazolyl having 1 to 2 substituents independently selected from the substituent group A on the ring; (b31) isothiazolyl; (b32) substituted isothiazolyl having 1 to 2 substituents independently selected from the substituent group A on the ring; (b33) thiadiazolyl; (b34) substituted thiadiazolyl having 1 substituent independently selected from the substituent group A on the ring; (b35) imidazopyridinyl; (b36) substituted imidazopyridinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b37) quinoxalinyl ; (b38) substituted quinoxalinyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b39) benzoxazolyl; (b40) substituted benzoxazolyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b41) benzimidazolyl; (b42) substituted benzimidazolyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b43) benzothiazolyl; (b44) substituted benzothiazolyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b45) thiazolopyridinyl; (b46) substituted thiazolopyridinyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b47) quinolyl;or (b48) a substituted quinolyl group having 1 to 6 substituents independently selected from Substituent Group A on the ring; R 5 is (i1) C1-C6 alkyl; or (i2) C1-C6 alkoxy C1-C6 alkyl, Substituent group A includes (e1) a halogen atom; (e2) a cyano group; (e4) a hydroxyl group; (e5) a carboxyl group; (e6) a C1-C6 alkyl group; (e9) a C1-C6 alkoxy group; (e10) a C3-C6 cycloalkyl group; (e11) a C1-C6 alkylthio group; (e12) a C1-C6 alkylsulfinyl group; (e13) a C1-C6 alkylsulfonyl group; (e14) a halogenated C1-C6 alkyl group -C6 alkyl; (e17) halogenated C1-C6 alkoxy; (e18) halogenated C3-C6 cycloalkyl; (e19) halogenated C1-C6 alkylthio; (e20) halogenated C1-C6 alkylsulfinyl; (e21) halogenated C1-C6 alkylsulfonyl; (e22) C1-C6 alkylcarbonylamino; (e24) C1-C6 alkylsulfonylamino; (e28) N -C1-C6 alkylcarboxamide; (e30) oxadiazolyl; (e31) a substituted oxadiazolyl having on the ring one substituent independently selected from a halogen atom, a cyano group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a C3-C6 cycloalkyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a halogenated C1-C6 alkyl group and a halogenated C1-C6 alkoxy group; (e32) a C1-C6 alkoxycarbonyl group; (e33) a methylenedioxy group optionally substituted with one or two substituents selected from a halogen atom, a phenyl group and a C1-C6 alkyl group; (e34) an N-C1-C6 alkylaminosulfonyl group; (e35) an N,N-diC1-C6 alkylaminosulfonyl group; (e36) R 6 -(R 7 -N=)O=S group, where R 6 represents a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a halogenated C1-C6 alkyl group or a C1-C6 alkoxy C1-C6 alkyl group, R 7 represents a hydrogen atom, a cyano group, a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a halogenated C1-C6 alkyl group, a C2-C6 alkylcarbonyl group or a halogenated C2-C6 alkylcarbonyl group; and (e37) a substituted C3-C6 cycloalkyl group having 1 to 3 substituents on the ring independently selected from a halogen atom, a cyano group, a C1-C6 alkyl group, a C1-C6 alkoxy group and a C1-C6 alkylcarbonyl group.

18. The compound or salt thereof according to claim 15 or 16, wherein R 1 is (a1) a hydrogen atom, R 2 (b5) phenyl; (b6) substituted phenyl having 1 to 5 substituents independently selected from the substituent group A on the ring; (b7) pyridyl; (b8) substituted pyridyl having 1 to 4 substituents independently selected from the substituent group A on the ring; (b9) pyridazinyl; (b10) substituted pyridazinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b11) pyrimidinyl; (b12) substituted pyrimidinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b13) pyrazinyl; (b14) substituted pyrazinyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b23) pyrazolyl; (b24) substituted pyrazolyl having 1 to 3 substituents independently selected from the substituent group A on the ring; (b27) triazolyl ; (b28) a substituted triazolyl group having 1 to 2 substituents independently selected from the substituent group A on the ring; (b29) a thiazolyl group; (b30) a substituted thiazolyl group having 1 to 2 substituents independently selected from the substituent group A on the ring; (b33) a thiadiazolyl group; (b34) a substituted thiadiazolyl group having 1 substituent independently selected from the substituent group A on the ring; (b43) a benzothiazolyl group; (b44) a substituted benzothiazolyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b45) a thiazolopyridyl group; (b46) a substituted thiazolopyridyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b47) a quinolyl group; or (b48) a substituted quinolyl group having 1 to 6 substituents independently selected from the substituent group A on the ring, R 5 is (i1) a C1-C6 alkyl group, Substituent group A includes (e1) a halogen atom; (e2) a cyano group; (e6) a C1-C6 alkyl group; (e9) a C1-C6 alkoxy group; (e11) a C1-C6 alkylthio group; (e12) a C1-C6 alkylsulfinyl group; (e13) a C1-C6 alkylsulfonyl group; (e14) a halogenated C1-C6 alkyl group; (e17) a halogenated C1-C6 alkoxy group; (e19) a halogenated C1-C6 alkylthio group; (e21) a halogenated C1-C6 alkylsulfonyl group; (e32) a C1-C6 alkoxycarbonyl group; (e34) an N-C1-C6 alkylaminosulfonyl group; and (e35) an N,N-diC1-C6 alkylaminosulfonyl group.

19. Use of the compound according to any one of claims 1 to 4 or its salt or N-oxide in the preparation of an external parasite control agent for animals.

20. Use of the compound according to any one of claims 1 to 4 or its salt or N-oxide in the preparation of an agent for controlling internal parasites for animals.

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