Aryltetrahydropyridazine derivatives or salts thereof, insecticides containing said compounds, and methods of using the same

Abstract

In the production of crops in agriculture, horticulture and the like, the occurrence of damages by pests and the like has been still a major issue, and therefore the development of novel agricultural / horticultural insecticides has been demanded due to the evolution of pests resistant to the existing chemicals and the like. The present invention has found that a compound represented by general formula (1) (wherein X and Y independently represent an oxygen atom or a sulfur atom; R1 represents a hydrogen atom or the like; R2 represents a substituted phenyl group or the like; R3 represents a hydrogen atom or the like; and R4 represents a substituted phenyl group or the like) or a salt thereof exerts a high insecticidal effect against pests and the like in the agricultural and horticultural realms, and provides an insecticide for agricultural / horticultural use which contains the compound or a salt thereof as an active ingredient and a method for using the insecticide.

Description

[Technical field]

[0001] The present invention relates to an aryltetrahydropyridazine derivative or a salt thereof, an insecticide containing said compound as an active ingredient, and a method for using the same. [Background technology]

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

[0003] [Patent Document 1] International Publication No. 2014 / 142273 Brochure Summary of the Invention [Problem to be solved by the invention]

[0004] Damage caused by pests and the like continues to be significant in agricultural and horticultural crop production, and the development of new insecticides and acaricides is desired due to factors such as the emergence of pests resistant to existing drugs. [Means for solving the problem]

[0005] Means for Solving the Problems The present inventors have conducted extensive research to develop novel insecticides, particularly agricultural and horticultural insecticides, and have found that the compound represented by the general formula (1) of the present invention, which has an aryltetrahydropyridazine derivative as the carboxylic acid moiety of the carboxamide, or a salt thereof, exhibits excellent effects as an insecticide, thereby completing the present invention.

[0006] That is, the present invention is [1] General formula (1) [ka] {where, R 1 (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 halo(C1-C6) alkyl group; (a8) a (C1-C6) alkylcarbonyl group; (a9) a (C1-C6) alkoxycarbonyl group; (a10) a substituted (C1-C6) alkyl group having one to three substituents on the chain independently selected from the group consisting of a cyano group, a (C1-C6) alkoxy group and a (C3-C6) cycloalkyl group; (a11) a thiazolylmethyl group; (a12) (a13) a benzyl group; or (a14) a substituted benzyl group having on the ring one to three substituents independently selected from the group consisting of a halogen atom, a (C1-C6) alkyl group, and a (C1-C6) alkoxy group. R 2 represents (b1) an aryl group; (b2) a substituted aryl group having on the ring one or more substituents independently selected from Substituent group A; (b3) a 5- to 10-membered heterocyclic group; or (b4) a substituted 5- to 10-membered heterocyclic group having on the ring one or more substituents independently selected from Substituent group A. However, R 2 is a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkylsulfonyl group, an N-(C1-C6) alkylaminosulfonyl group, an N,N-di(C1-C6) alkylaminosulfonyl group, or a R 6 -(R 7 -N=)O=S group (in the formula, R 6 represents a (C1-C6) alkyl group, a (C3-C6) cycloalkyl group, a halo(C1-C6) alkyl group, or a (C1-C6) alkoxy(C1-C6) alkyl group; R 7represents a hydrogen atom, a cyano group, a (C1-C6)alkyl group, a (C3-C6)cycloalkyl group, a halo(C1-C6)alkyl group, a (C2-C6)alkylcarbonyl group, or a halo(C2-C6)alkylcarbonyl group. ) is not substituted. 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. R 4(d1) a (C1-C6) alkyl group; (d2) a (C2-C6) alkenyl group; (d3) a (C2-C6) alkynyl group; (d4) a (C3-C6) cycloalkyl group; (d5) a halo(C1-C6) alkyl group; (d6) a halo(C2-C6) alkenyl group; (d7) a halo(C2-C6) alkynyl group; (d8) a substituted (C1-C6) alkyl group having 1 to 3 substituents independently selected from the substituent group B; (d9) a substituted (C3-C6) cycloalkyl group having on the ring 1 to 3 substituents independently selected from the substituent group C; (d10) a (C1-C6) alkylsulfonyl group; (d11) an N-(C1-C6) alkylsulfamoyl group; (d12) a phenyl group; (d13) A substituted phenyl group having 1 to 5 substituents on the ring, each independently selected from the substituent group D; (d14) a phenyl(C1-C6)alkyl group; (d15) a substituted phenyl(C1-C6)alkyl group having 1 to 5 substituents on the ring, each independently selected from the substituent group D; (d16) a pyridyl group; (d17) a substituted pyridyl group having 1 to 4 substituents on the ring, each independently selected from the substituent group D; (d18) a pyridazinyl group; (d19) a substituted pyridazinyl group having 1 to 3 substituents on the ring, each independently selected from the substituent group D; (d20) a pyrimidinyl group; (d21) a substituted pyrimidinyl group having 1 to 3 substituents on the ring, each independently selected from the substituent group D; (d22) a pyrazinyl group; (d23) a substituted pyrazinyl group having 1 to 3 substituents on the ring, each independently selected from the substituent group D; (d24) a pyrazolyl group; (d25) a substituted pyrazolyl group having 1 to 3 substituents each independently selected from the substituent group D on the ring; (d26) an isoxazolyl group; (d27) a substituted isoxazolyl group having 1 to 2 substituents each independently selected from the substituent group D on the ring; (d28) an isothiazolyl group; (d29) a substituted isothiazolyl group having 1 to 2 substituents each independently selected from the substituent group D on the ring; (d30) an oxazolyl group; (d31) a substituted oxazolyl group having 1 to 2 substituents each independently selected from the substituent group D on the ring; (d32) a thiazolyl group;(d33) a substituted thiazolyl group having on the ring one or two substituents each independently selected from the substituent group D; (d34) a triazolyl group; (d35) a substituted triazolyl group having on the ring one or two substituents each independently selected from the substituent group D; (d36) a thiadiazolyl group; (d37) a substituted thiadiazolyl group having on the ring one substituent each independently selected from the substituent group D; (d38) a tetrazolyl group; (d39) a substituted tetrazolyl group having on the ring one substituent each independently selected from the substituent group D; (d40) a triazinyl group; (d41) a substituted triazinyl group having on the ring one or two substituents each independently selected from the substituent group D; (d42) a furyl(C1-C6)alkyl group; (d43) Substituted furyl(C1-C6)alkyl groups having 1 to 3 substituents on the ring, each independently selected from the substituent group D; (d44) thienyl(C1-C6)alkyl groups; (d45) substituted thienyl(C1-C6)alkyl groups having 1 to 3 substituents on the ring, each independently selected from the substituent group D; (d46) quinolinyl groups; (d47) substituted quinolinyl groups having 1 to 6 substituents on the ring, each independently selected from the substituent group D; (d48) benzothiazolyl groups; (d49) substituted benzothiazolyl groups having 1 to 4 substituents on the ring, each independently selected from the substituent group D; (d50) pyridyl(C1-C6)alkyl groups; (d51) substituted pyridyl(C1-C6)alkyl groups having 1 to 4 substituents on the ring, each independently selected from the substituent group D; (d52) pyrazinyl(C1-C6)alkyl group; (d53) a substituted pyrazinyl(C1-C6)alkyl group having 1 to 3 substituents independently selected from the substituent group D on the ring; (d54) a naphthyl group; (d55) a substituted naphthyl group having 1 to 7 substituents independently selected from the substituent group D on the ring; (d56) a tetrahydronaphthyl group; or (d57) a substituted tetrahydronaphthyl group having 1 to 10 substituents independently selected from the 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 halo(C1-C6) alkyl group; (e15) a halo(C2-C6) alkenyl group; (e16) a halo(C2-C6) alkynyl group; (e17). Halo(C1-C6)alkoxy group;(e18) halo(C3-C6)cycloalkyl group;(e19) halo(C1-C6)alkylthio group;(e20) halo(C1-C6)alkylsulfinyl group;(e21) halo(C1-C6)alkylsulfonyl group;(e22) (C1-C6)alkylcarbonylamino group;(e23) halo(C1-C6)alkylcarbonylamino group;(e24) (C1-C6)alkylsulfonylamino group;(e25) halo(C1-C6)alkylsulfonylamino group;(e26) SF5 group;(e27) (C1-C6)alkoxy(C1-C6)alkyl group;(e28) N-(C1-C6)alkylcarboxamide group;(e29) an N-halo(C1-C6)alkylcarboxamide group; (e30) an oxadiazolyl group; (e31) a substituted oxadiazolyl group having on the ring one substituent independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6)alkyl group, a (C1-C6)alkoxy group, a (C3-C6)cycloalkyl group, a (C1-C6)alkylthio group, a (C1-C6)alkylsulfinyl group, a (C1-C6)alkylsulfonyl group, a halo(C1-C6)alkyl group and a halo(C1-C6)alkoxy group; (e32) a (C1-C6)alkoxycarbonyl group; (e33) a methylenedioxy group which may be substituted by one or two substituents selected from the group consisting of a halogen atom, a phenyl group and a (C1-C6)alkyl group, formed together by two adjacent substituents; (e34) an N-(C1-C6)alkylaminosulfonyl group;(e35) N,N-di(C1-C6)alkylaminosulfonyl group; (e36) R; 6 -(R 7 -N=)O=S group (in the formula, R 6 represents a (C1-C6) alkyl group, a (C3-C6) cycloalkyl group, a halo(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 halo(C1-C6)alkyl group, a (C2-C6)alkylcarbonyl group, or a halo(C2-C6)alkylcarbonyl group; and (e37) a substituted (C3-C6)cycloalkyl group having 1 to 3 substituents on the ring independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6)alkyl group, a (C1-C6)alkoxy group, and a (C1-C6)alkylcarbonyl group. Substituent group B consists of (f1) a cyano group; (f2) a (C3-C6)cycloalkyl group; (f3) a (C1-C6)alkoxy group; (f4) a (C1-C6)alkylthio group; (f5) a (C1-C6)alkylsulfinyl group; (f6) a (C1-C6)alkylsulfonyl group; (f7) a halo(C3-C6)cycloalkyl group; (f8) a halo(C1-C6)alkoxy group; (f9) a halo(C1-C6)alkylthio group; (f10) a halo(C1-C6)alkylsulfinyl group; (f11) a halo(C1-C6)alkylsulfonyl group; (f12) a carboxamide group; and (f13) a phenylcarbonyl group. Substituent group C includes (g1) a cyano group; (g2) a (C1-C6) alkyl group; (g3) a (C3-C6) cycloalkyl group; (g4) a (C1-C6) alkoxy group; (g5) a (C1-C6) alkylthio group; (g6) a (C1-C6) alkylsulfinyl group; (g7) a (C1-C6) alkylsulfonyl group; (g8) a halo(C3-C6) cycloalkyl group; (g9) a halo(C1-C6) alkoxy group; (g10) a halo(C1-C6) alkylthio group; (g11) a halo(C1-C6) alkylsulfinyl group; (g12) a halo(C1-C6) alkylsulfonyl group; (g13) a halo(C1-C6) alkyl group; (g14) a carboxamide group; (g15) a (C2-C6) alkynyl group; and (g16). It consists of a phenyl group. Substituent group D includes (h1) halogen atoms; (h2) cyano groups; (h3) hydroxyl groups; (h4) carboxyl groups; (h5) (C1-C6) alkyl groups; (h6) (C1-C6) alkoxy groups; (h7) (C3-C6) cycloalkyl groups; (h8) (C1-C6) alkylthio groups; (h9) (C1-C6) alkylsulfinyl groups; (h10) (C1-C6) alkylsulfonyl groups; (h11) halo(C1-C6) alkyl groups; (h12) halo(C1-C6) alkoxy groups; (h13) halo(C3-C6) cycloalkyl groups; (h14) halo(C1-C6) alkylthio groups; (h15) halo(C1-C6) alkylsulfinyl groups; (h16) halo(C1-C6) alkylsulfonyl groups; (h17). (h18) an N-(C1-C6)alkylcarboxamide group; (h19) an N-halo(C1-C6)alkylcarboxamide group; (h20) a methylenedioxy group which may be substituted with one or two substituents selected from the group consisting of a halogen atom, a phenyl group, and a (C1-C6)alkyl group, formed by two adjacent substituents taken together; (h21) a nitro group; (h22) an amino group; and (h23) a benzyloxycarbonyl group.} and salts thereof, [2]R 1 , R 3 , R 4, X, Y, and the substituent groups A, B, C, and D are the same as those in [1]; R 2(b5) a phenyl group; (b6) a substituted phenyl group having 1 to 5 substituents each independently selected from the substituent group A on the ring; (b7) a pyridyl group; (b8) a substituted pyridyl group having 1 to 4 substituents each independently selected from the substituent group A on the ring; (b9) a pyridazinyl group; (b10) a substituted pyridazinyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (b11) a pyrimidinyl group; (b12) a substituted pyrimidinyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (b13) a pyrazinyl group; (b14) a substituted pyrazinyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (b15) a furyl group; (b16) a substituted furyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (b17) a thienyl group; (b18) a substituted thienyl group having one to three substituents independently selected from the substituent group A on the ring; (b19) an isoxazolyl group; (b20) a substituted isoxazolyl group having one to two substituents independently selected from the substituent group A on the ring; (b21) an oxazolyl group; (b22) a substituted oxazolyl group having one to two substituents independently selected from the substituent group A on the ring; (b23) a pyrazolyl group; (b24) a substituted pyrazolyl group having one to three substituents independently selected from the substituent group A on the ring; (b25) an imidazolyl group; (b26) a substituted imidazolyl group having one to three substituents independently selected from the substituent group A on the ring; (b27) a triazolyl group; (b28) a substituted triazolyl group having on the ring one or two substituents each independently selected from the substituent group A; (b29) a thiazolyl group; (b30) a substituted thiazolyl group having on the ring one or two substituents each independently selected from the substituent group A; (b31) an isothiazolyl group; (b32) a substituted isothiazolyl group having on the ring one or two substituents each independently selected from the substituent group A; (b33) a thiadiazolyl group; (b34) a substituted thiadiazolyl group having on the ring one substituent each independently selected from the substituent group A; (b35) an imidazopyridyl group;(b36) a substituted imidazopyridyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b37) a quinoxalinyl group; (b38) a substituted quinoxalinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b39) a benzoxazolyl group; (b40) a substituted benzoxazolyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b41) a benzimidazolyl group; (b42) a substituted benzimidazolyl group having 1 to 5 substituents 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 on the ring, each independently selected from the substituent group A; (b47) a quinolinyl group; (b48) a substituted quinolinyl group having 1 to 6 substituents on the ring, each independently selected from the substituent group A; (b49) a naphthyl group; (b50) a substituted naphthyl group having 1 to 7 substituents on the ring, each independently selected from the substituent group A; (b51) a triazinyl group; (b52) a substituted triazinyl group having 1 to 2 substituents on the ring, each independently selected from the substituent group A; (b53) a pyrrolyl group; (b54) a substituted pyrrolyl group having 1 to 4 substituents on the ring, each independently selected from the substituent group A; (b55) a tetrazolyl group; (b56) a substituted tetrazolyl group having one substituent on the ring, each independently selected from the substituent group A; (b57) an oxadiazonyl group; (b58) a substituted oxadiazonyl group having one substituent independently selected from the substituent group A on the ring; (b59) a 2-oxopyridyl group; (b60) a substituted 2-oxopyridyl group having one to four substituents independently selected from the substituent group A on the ring; (b61) a benzofuranyl group; (b62) a substituted benzofuranyl group having one to five substituents independently selected from the substituent group A on the ring; (b63) a benzoisoxazolyl group; (b64) a substituted benzoisoxazolyl group having one to four substituents independently selected from the substituent group A on the ring;(b65) a benzothienyl group; (b66) a substituted benzothienyl group having 1 to 5 substituents each independently selected from the substituent group A on the ring; (b67) a benzoisothiazolyl group; (b68) a substituted benzoisothiazolyl group having 1 to 4 substituents each independently selected from the substituent group A on the ring; (b69) an indolyl group; (b70) a substituted indolyl group having 1 to 6 substituents each independently selected from the substituent group A on the ring; (b71) an isoindolyl group; (b72) a substituted isoindolyl group having 1 to 6 substituents each independently selected from the substituent group A on the ring; (b73) an indazolyl group; (b74) a substituted indazolyl group having 1 to 5 substituents each independently selected from the substituent group A on the ring; (b75) a benzotriazolyl group; (b76) A substituted benzotriazolyl group having 1 to 4 substituents on the ring, each independently selected from the substituent group A; (b77) a furopyridyl group; (b78) a substituted furopyridyl group having 1 to 4 substituents on the ring, each independently selected from the substituent group A; (b79) a thienopyridyl group; (b80) a substituted thienopyridyl group having 1 to 4 substituents on the ring, each independently selected from the substituent group A; (b81) an indolizinyl group; (b82) a substituted indolizinyl group having 1 to 6 substituents on the ring, each independently selected from the substituent group A; (b83) a pyrrolopyridyl group; (b84) a substituted pyrrolopyridyl group having 1 to 5 substituents on the ring, each independently selected from the substituent group A; (b85) a pyrrolopyrimidinyl group; (b86) a substituted pyrrolopyrimidinyl group having 1 to 5 substituents each independently selected from the substituent group A on the ring; (b87) an oxazolopyridyl group; (b88) a substituted oxazolopyridyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (b89) an isoxazolopyridyl group; (b90) a substituted isoxazolopyridyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (b91) an isothiazolopyridyl group; (b92) a substituted isothiazolopyridyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (b93) an imidazopyrimidinyl group;(b94) a substituted imidazopyrimidinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b95) a pyrazolopyridyl group; (b96) a substituted pyrazolopyridyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b97) a pyrazolopyrimidinyl group; (b98) a substituted pyrazolopyrimidinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b99) a triazolopyridyl group; (b100) a substituted triazolopyridyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b101) a triazolopyrimidinyl group; (b102) a substituted triazolopyrimidinyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b103) an isoquinolinyl group; (b104) a substituted isoquinolinyl group having 1 to 6 substituents independently selected from the substituent group A on the ring; (b105) a cinnolinyl group; (b106) a substituted cinnolinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b107) a phthalazinyl group; (b108) a substituted phthalazinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b109) a quinazolinyl group; (b110) a substituted quinazolinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b111) a naphthyridinyl group; or (b112) a substituted naphthyridinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; [3] R 1 is (a1) a hydrogen atom; (a2) a (C1-C6) alkyl group; or (a4) a (C2-C6) alkynyl group; R 2(b5) a phenyl group; (b6) a substituted phenyl group having 1 to 5 substituents each independently selected from the substituent group A on the ring; (b7) a pyridyl group; (b8) a substituted pyridyl group having 1 to 4 substituents each independently selected from the substituent group A on the ring; (b9) a pyridazinyl group; (b10) a substituted pyridazinyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (b11) a pyrimidinyl group; (b12) a substituted pyrimidinyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (b13) a pyrazinyl group; (b14) a substituted pyrazinyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (b15) a furyl group; (b16) a substituted furyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (b17) a thienyl group; (b18) a substituted thienyl group having one to three substituents independently selected from the substituent group A on the ring; (b19) an isoxazolyl group; (b20) a substituted isoxazolyl group having one to two substituents independently selected from the substituent group A on the ring; (b21) an oxazolyl group; (b22) a substituted oxazolyl group having one to two substituents independently selected from the substituent group A on the ring; (b23) a pyrazolyl group; (b24) a substituted pyrazolyl group having one to three substituents independently selected from the substituent group A on the ring; (b25) an imidazolyl group; (b26) a substituted imidazolyl group having one to three substituents independently selected from the substituent group A on the ring; (b27) a triazolyl group; (b28) a substituted triazolyl group having on the ring one or two substituents each independently selected from the substituent group A; (b29) a thiazolyl group; (b30) a substituted thiazolyl group having on the ring one or two substituents each independently selected from the substituent group A; (b31) an isothiazolyl group; (b32) a substituted isothiazolyl group having on the ring one or two substituents each independently selected from the substituent group A; (b33) a thiadiazolyl group; (b34) a substituted thiadiazolyl group having on the ring one substituent each independently selected from the substituent group A; (b35) an imidazopyridyl group;(b36) a substituted imidazopyridyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b37) a quinoxalinyl group; (b38) a substituted quinoxalinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b39) a benzoxazolyl group; (b40) a substituted benzoxazolyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b41) a benzimidazolyl group; (b42) a substituted benzimidazolyl group having 1 to 5 substituents 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 quinolinyl group; or (b48) a substituted quinolinyl 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) a (C1-C6) alkyl group; (d2) a (C2-C6) alkenyl group; (d3) a (C2-C6) alkynyl group; (d4) a (C3-C6) cycloalkyl group; (d5) a halo(C1-C6) alkyl group; (d8) a substituted (C1-C6) alkyl group having 1 to 3 substituents independently selected from the substituent group B; (d9) a substituted (C3-C6) cycloalkyl group having 1 to 3 substituents independently selected from the substituent group C on the ring; (d10) a (C1-C6) alkylsulfonyl group; (d11) an N-(C1-C6) alkylsulfamoyl group; (d12) a phenyl group; (d13) a substituted phenyl group having 1 to 5 substituents independently selected from the substituent group D on the ring; (d14) a phenyl(C1-C6) alkyl group; (d15) a substituted phenyl(C1-C6)alkyl group having 1 to 5 substituents on the ring, each independently selected from the substituent group D; (d16) a pyridyl group; (d17) a substituted pyridyl group having 1 to 4 substituents on the ring, each independently selected from the substituent group D; (d18) a pyridazinyl group; (d19) a substituted pyridazinyl group having 1 to 3 substituents on the ring, each independently selected from the substituent group D; (d20) a pyrimidinyl group; (d21) a substituted pyrimidinyl group having 1 to 3 substituents on the ring, each independently selected from the substituent group D; (d22) a pyrazinyl group; (d23) a substituted pyrazinyl group having 1 to 3 substituents on the ring, each independently selected from the substituent group D; (d24) a pyrazolyl group; (d25) a substituted pyrazolyl group having 1 to 3 substituents on the ring, each independently selected from the substituent group D; (d26) an isoxazolyl group; (d27) a substituted isoxazolyl group having on the ring one to two substituents each independently selected from the substituent group D; (d28) an isothiazolyl group; (d29) a substituted isothiazolyl group having on the ring one to two substituents each independently selected from the substituent group D; (d30) an oxazolyl group; (d31) a substituted oxazolyl group having on the ring one to two substituents each independently selected from the substituent group D; (d32) a thiazolyl group; (d33) a substituted thiazolyl group having on the ring one to two substituents each independently selected from the substituent group D; (d34) a triazolyl group;(d35) a substituted triazolyl group having one or two substituents independently selected from the substituent group D on the ring; (d36) a thiadiazolyl group; (d37) a substituted thiadiazolyl group having one substituent independently selected from the substituent group D on the ring; (d38) a tetrazolyl group; (d39) a substituted tetrazolyl group having one substituent independently selected from the substituent group D on the ring; (d40) a triazinyl group; (d41) a substituted triazinyl group having one or two substituents independently selected from the substituent group D on the ring; (d42) a furyl(C1-C6)alkyl group; (d43) a substituted furyl(C1-C6)alkyl group having one to three substituents independently selected from the substituent group D on the ring; (d44) a thienyl(C1-C6)alkyl group; (d45) a substituted thienyl(C1-C6)alkyl group having 1 to 3 substituents on the ring, each independently selected from the substituent group D; (d46) a quinolinyl group; (d47) a substituted quinolinyl group having 1 to 6 substituents on the ring, each independently selected from the substituent group D; (d48) a benzothiazolyl group; (d49) a substituted benzothiazolyl group having 1 to 4 substituents on the ring, each independently selected from the substituent group D; (d50) a pyridyl(C1-C6)alkyl group; (d51) a substituted pyridyl(C1-C6)alkyl group having 1 to 4 substituents on the ring, each independently selected from the substituent group D; (d52) a pyrazinyl(C1-C6)alkyl group; (d53) a substituted pyrazinyl(C1-C6)alkyl group having 1 to 3 substituents on the ring, each independently selected from the substituent group D; (d54) a naphthyl group; (d55) a substituted naphthyl group having 1 to 7 substituents on the ring, each independently selected from the substituent group D; (d56) a tetrahydronaphthyl group; or (d57) a substituted tetrahydronaphthyl group having 1 to 10 substituents on the ring, each independently selected from the substituent group D; 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 halo(C1-C6) alkyl group; (e17) a halo(C1-C6) alkoxy group; (e18) a halo(C3-C6) cycloalkyl group; (e19) a halo(C1-C6) alkylthio group; (e20) a halo(C1-C6) alkylsulfinyl group; (e21) a halo(C1-C6) alkylsulfonyl group; (e22). (C1-C6)alkylcarbonylamino group;(e24) (C1-C6)alkylsulfonylamino group;(e28) N-(C1-C6)alkylcarboxamide group;(e30) oxadiazolyl group;(e31) a substituted oxadiazolyl group having on the ring one substituent independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6)alkyl group, a (C1-C6)alkoxy group, a (C3-C6)cycloalkyl group, a (C1-C6)alkylthio group, a (C1-C6)alkylsulfinyl group, a (C1-C6)alkylsulfonyl group, a halo(C1-C6)alkyl group and a halo(C1-C6)alkoxy group;(e32) a (C1-C6)alkoxycarbonyl group;(e33) a methylenedioxy group which may be substituted by one or two substituents selected from the group consisting of halogen atoms, phenyl groups and (C1-C6) alkyl groups, formed by two adjacent substituents taken together; (e34) an N-(C1-C6) alkylaminosulfonyl group; (e35) an N,N-di(C1-C6) alkylaminosulfonyl group; (e36) R 6 -(R 7 -N=)O=S group (in the formula, R 6 represents a (C1-C6) alkyl group, a (C3-C6) cycloalkyl group, a halo(C1-C6) alkyl group, or a (C1-C6) alkoxy(C1-C6) alkyl group; R 7represents a hydrogen atom, a cyano group, a (C1-C6)alkyl group, a (C3-C6)cycloalkyl group, a halo(C1-C6)alkyl group, a (C2-C6)alkylcarbonyl group, or a halo(C2-C6)alkylcarbonyl group; and (e37) a substituted (C3-C6)cycloalkyl group having 1 to 3 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6)alkyl group, a (C1-C6)alkoxy group, and a (C1-C6)alkylcarbonyl group, Substituent group B consists of (f1) a cyano group; (f2) a (C3-C6)cycloalkyl group; (f3) a (C1-C6)alkoxy group; (f4) a (C1-C6)alkylthio group; (f5) a (C1-C6)alkylsulfinyl group; (f6) a (C1-C6)alkylsulfonyl group; (f7) a halo(C3-C6)cycloalkyl group; (f8) a halo(C1-C6)alkoxy group; (f9) a halo(C1-C6)alkylthio group; (f10) a halo(C1-C6)alkylsulfinyl group; and (f11) a halo(C1-C6)alkylsulfonyl group; Substituent group C consists of (g1) a cyano group; (g2) a (C1-C6) alkyl group; (g3) a (C3-C6) cycloalkyl group; (g4) a (C1-C6) alkoxy group; (g5) a (C1-C6) alkylthio group; (g6) a (C1-C6) alkylsulfinyl group; (g7) a (C1-C6) alkylsulfonyl group; (g8) a halo(C3-C6) cycloalkyl group; (g9) a halo(C1-C6) alkoxy group; (g10) a halo(C1-C6) alkylthio group; (g11) a halo(C1-C6) alkylsulfinyl group; (g12) a halo(C1-C6) alkylsulfonyl group; (g13) a halo(C1-C6) alkyl group; (g15) a (C2-C6) alkynyl group; and (g16) a phenyl group; Substituent group D includes (h1) halogen atoms; (h2) cyano groups; (h3) hydroxyl groups; (h4) carboxyl groups; (h5) (C1-C6) alkyl groups; (h6) (C1-C6) alkoxy groups; (h7) (C3-C6) cycloalkyl groups; (h8) (C1-C6) alkylthio groups; (h9) (C1-C6) alkylsulfinyl groups; (h10) (C1-C6) alkylsulfonyl groups; (h11) halo(C1-C6) alkyl groups; (h12) halo(C1-C6) alkoxy groups; (h13) halo(C3-C6) cycloalkyl groups; (h14) halo(C1-C6) alkylthio groups; (h15) halo(C1-C6) alkylsulfinyl groups; (h16) halo(C1-C6) alkylsulfonyl groups; (h17). (h18) an N-(C1-C6)alkylcarboxamide group; (h20) a methylenedioxy group which may be substituted by one or two substituents selected from the group consisting of a halogen atom, a phenyl group, and a (C1-C6)alkyl group, formed by two adjacent substituents taken together; (h21) a nitro group; (h22) an amino group; and (h23) a benzyloxycarbonyl group, [4]R 1 (a1) is a hydrogen atom; R 2(b5) a phenyl group; (b6) a substituted phenyl group having 1 to 5 substituents each independently selected from the substituent group A on the ring; (b7) a pyridyl group; (b8) a substituted pyridyl group having 1 to 4 substituents each independently selected from the substituent group A on the ring; (b9) a pyridazinyl group; (b10) a substituted pyridazinyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (b11) a pyrimidinyl group; (b12) a substituted pyrimidinyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (b13) a pyrazinyl group; (b14) a substituted pyrazinyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (b23) a pyrazolyl group; (b24). a substituted pyrazolyl group having one to three substituents independently selected from the substituent group A on the ring; (b27) a triazolyl group; (b28) a substituted triazolyl group having one to two substituents independently selected from the substituent group A on the ring; (b29) a thiazolyl group; (b30) a substituted thiazolyl group having one to two substituents independently selected from the substituent group A on the ring; (b33) a thiadiazolyl group; (b34) a substituted thiadiazolyl group having one substituent independently selected from the substituent group A on the ring; (b43) a benzothiazolyl group; (b44) a substituted benzothiazolyl group having one to four substituents independently selected from the substituent group A on the ring; (b45) a thiazolopyridyl group; (b46) a substituted thiazolopyridyl group having one to four substituents independently selected from the substituent group A on the ring; (b47) a quinolinyl group; or (b48) a substituted quinolinyl 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) a (C1-C6) alkyl group; (d2) a (C2-C6) alkenyl group; (d3) a (C2-C6) alkynyl group; (d4) a (C3-C6) cycloalkyl group; (d5) a halo(C1-C6) alkyl group; (d8) a substituted (C1-C6) alkyl group having 1 to 3 substituents independently selected from the substituent group B; (d9) a substituted (C3-C6) cycloalkyl group having 1 to 3 substituents independently selected from the substituent group C on the ring; (d12) a phenyl group; (d13) a substituted phenyl group having 1 to 5 substituents independently selected from the substituent group D on the ring; (d14) a phenyl(C1-C6) alkyl group; (d15) a substituted phenyl(C1-C6) alkyl group having 1 to 5 substituents independently selected from the substituent group D on the ring; (d16) a pyridyl group; (d17) a substituted pyridyl group having 1 to 4 substituents on the ring, each independently selected from the substituent group D; (d18) a pyridazinyl group; (d19) a substituted pyridazinyl group having 1 to 3 substituents on the ring, each independently selected from the substituent group D; (d20) a pyrimidinyl group; (d21) a substituted pyrimidinyl group having 1 to 3 substituents on the ring, each independently selected from the substituent group D; (d22) a pyrazinyl group; (d24) a pyrazolyl group; (d25) a substituted pyrazolyl group having 1 to 3 substituents on the ring, each independently selected from the substituent group D; (d26) an isoxazolyl group; (d27) a substituted isoxazolyl group having 1 to 2 substituents on the ring, each independently selected from the substituent group D; (d32) a thiazolyl group; (d33) a substituted thiazolyl group having on the ring one or two substituents each independently selected from the substituent group D; (d34) a triazolyl group; (d35) a substituted triazolyl group having on the ring one or two substituents each independently selected from the substituent group D; (d36) a thiadiazolyl group; (d37) a substituted thiadiazolyl group having on the ring one substituent each independently selected from the substituent group D; (d42) a furyl(C1-C6)alkyl group; (d43) a substituted furyl(C1-C6)alkyl group having on the ring one or three substituents each independently selected from the substituent group D; (d44) a thienyl(C1-C6)alkyl group;(d45) a substituted thienyl(C1-C6)alkyl group having 1 to 3 substituents on the ring, each independently selected from the substituent group D; (d46) a quinolinyl group; (d47) a substituted quinolinyl group having 1 to 6 substituents on the ring, each independently selected from the substituent group D; (d48) a benzothiazolyl group; (d49) a substituted benzothiazolyl group having 1 to 4 substituents on the ring, each independently selected from the substituent group D; (d50) a pyridyl(C1-C6)alkyl group; (d51) a substituted pyridyl(C1-C6)alkyl group having 1 to 4 substituents on the ring, each independently selected from the substituent group D; (d52) a pyrazinyl(C1-C6)alkyl group; (d53) a substituted pyrazinyl(C1-C6)alkyl group having 1 to 3 substituents on the ring, each independently selected from the substituent group D; (d54) a naphthyl group; (d55) a substituted naphthyl group having 1 to 7 substituents independently selected from the substituent group D on the ring; (d56) a tetrahydronaphthyl group; or (d57) a substituted tetrahydronaphthyl group having 1 to 10 substituents independently selected from the substituent group D on the ring; Substituent group A consists of (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. Substituent group B consists of (f1) a cyano group; (f2) a (C3-C6) cycloalkyl group; (f3) a (C1-C6) alkoxy group; and (f4) a (C1-C6) alkylthio group; Substituent group C consists of (g1) a cyano group; (g2) a (C1-C6) alkyl group; (g13) a halo(C1-C6) alkyl group; (g15) a (C2-C6) alkynyl group; and (g16) a phenyl group; the compound or salt thereof according to any one of [1] to [3], wherein Substituent Group D consists of (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 which may be substituted by one or two substituents selected from the group consisting of a halogen atom, a phenyl group, and a (C1-C6)alkyl group, which are formed together by two adjacent substituents; and (h21) a nitro group; [5] An insecticide comprising the compound according to any one of [1] to [4] or its salt or N-oxide as an active ingredient. [6] An agricultural and horticultural insecticide comprising the compound according to any one of [1] to [4] or its salt or N-oxide as an active ingredient. [7] An animal ectoparasite control agent, comprising the compound according to any one of [1] to [4] or a salt or N-oxide thereof as an active ingredient. [8] An animal internal parasite control agent, comprising the compound according to any one of [1] to [4] or a salt or N-oxide thereof as an active ingredient. [9] A method for using an insecticide, comprising applying an effective amount of the insecticide according to [5] or [6] to a plant or soil.

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

[0007]

[11] General formula (13A) [ka] {where, R1 (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 halo(C1-C6) alkyl group; (a8) a (C1-C6) alkylcarbonyl group; (a9) a (C1-C6) alkoxycarbonyl group; (a10) a substituted (C1-C6) alkyl group having one to three substituents on the chain independently selected from the group consisting of a cyano group, a (C1-C6) alkoxy group and a (C3-C6) cycloalkyl group; (a11) a thiazolylmethyl group; (a12) (a13) a benzyl group; or (a14) a substituted benzyl group having on the ring one to three substituents independently selected from the group consisting of a halogen atom, a (C1-C6) alkyl group, and a (C1-C6) alkoxy group. R 2 represents (b1) an aryl group; (b2) a substituted aryl group having on the ring one or more substituents independently selected from Substituent group A; (b3) a 5- to 10-membered heterocyclic group; or (b4) a substituted 5- to 10-membered heterocyclic group having on the ring one or more substituents independently selected from Substituent group A. However, R 2 is a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkylsulfonyl group, an N-(C1-C6) alkylaminosulfonyl group, an N,N-di(C1-C6) alkylaminosulfonyl group, or a R 6 -(R 7 -N=)O=S group (in the formula, R 6 represents a (C1-C6) alkyl group, a (C3-C6) cycloalkyl group, a halo(C1-C6) alkyl group, or a (C1-C6) alkoxy(C1-C6) alkyl group; R 7represents a hydrogen atom, a cyano group, a (C1-C6)alkyl group, a (C3-C6)cycloalkyl group, a halo(C1-C6)alkyl group, a (C2-C6)alkylcarbonyl group, or a halo(C2-C6)alkylcarbonyl group. ) is not substituted. 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 halo(C1-C6) alkyl group; (e15) a halo(C2-C6) alkenyl group; (e16) a halo(C2-C6) alkynyl group; (e17). Halo(C1-C6)alkoxy group;(e18) halo(C3-C6)cycloalkyl group;(e19) halo(C1-C6)alkylthio group;(e20) halo(C1-C6)alkylsulfinyl group;(e21) halo(C1-C6)alkylsulfonyl group;(e22) (C1-C6)alkylcarbonylamino group;(e23) halo(C1-C6)alkylcarbonylamino group;(e24) (C1-C6)alkylsulfonylamino group;(e25) halo(C1-C6)alkylsulfonylamino group;(e26) SF5 group;(e27) (C1-C6)alkoxy(C1-C6)alkyl group;(e28) N-(C1-C6)alkylcarboxamide group;(e29) an N-halo(C1-C6)alkylcarboxamide group; (e30) an oxadiazolyl group; (e31) a substituted oxadiazolyl group having on the ring one substituent independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6)alkyl group, a (C1-C6)alkoxy group, a (C3-C6)cycloalkyl group, a (C1-C6)alkylthio group, a (C1-C6)alkylsulfinyl group, a (C1-C6)alkylsulfonyl group, a halo(C1-C6)alkyl group and a halo(C1-C6)alkoxy group; (e32) a (C1-C6)alkoxycarbonyl group; (e33) a methylenedioxy group which may be substituted by one or two substituents selected from the group consisting of a halogen atom, a phenyl group and a (C1-C6)alkyl group, formed together by two adjacent substituents; (e34) an N-(C1-C6)alkylaminosulfonyl group;(e35) N,N-di(C1-C6)alkylaminosulfonyl group (e36) R; 6 -(R 7 -N=)O=S group (in the formula, R 6 represents a (C1-C6) alkyl group, a (C3-C6) cycloalkyl group, a halo(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 halo(C1-C6) alkyl group, a (C2-C6) alkylcarbonyl group, or a halo(C2-C6) alkylcarbonyl group; and (e37) a substituted (C3-C6) cycloalkyl group having 1 to 3 substituents on the ring independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, and a (C1-C6) alkylcarbonyl group.} and salts thereof,

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

[11] , R 2(b5) a phenyl group; (b6) a substituted phenyl group having 1 to 5 substituents each independently selected from the substituent group A on the ring; (b7) a pyridyl group; (b8) a substituted pyridyl group having 1 to 4 substituents each independently selected from the substituent group A on the ring; (b9) a pyridazinyl group; (b10) a substituted pyridazinyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (b11) a pyrimidinyl group; (b12) a substituted pyrimidinyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (b13) a pyrazinyl group; (b14) a substituted pyrazinyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (b15) a furyl group; (b16) a substituted furyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (b17) a thienyl group; (b18) a substituted thienyl group having one to three substituents independently selected from the substituent group A on the ring; (b19) an isoxazolyl group; (b20) a substituted isoxazolyl group having one to two substituents independently selected from the substituent group A on the ring; (b21) an oxazolyl group; (b22) a substituted oxazolyl group having one to two substituents independently selected from the substituent group A on the ring; (b23) a pyrazolyl group; (b24) a substituted pyrazolyl group having one to three substituents independently selected from the substituent group A on the ring; (b25) an imidazolyl group; (b26) a substituted imidazolyl group having one to three substituents independently selected from the substituent group A on the ring; (b27) a triazolyl group; (b28) a substituted triazolyl group having on the ring one or two substituents each independently selected from the substituent group A; (b29) a thiazolyl group; (b30) a substituted thiazolyl group having on the ring one or two substituents each independently selected from the substituent group A; (b31) an isothiazolyl group; (b32) a substituted isothiazolyl group having on the ring one or two substituents each independently selected from the substituent group A; (b33) a thiadiazolyl group; (b34) a substituted thiadiazolyl group having on the ring one substituent each independently selected from the substituent group A; (b35) an imidazopyridyl group;(b36) a substituted imidazopyridyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b37) a quinoxalinyl group; (b38) a substituted quinoxalinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b39) a benzoxazolyl group; (b40) a substituted benzoxazolyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b41) a benzimidazolyl group; (b42) a substituted benzimidazolyl group having 1 to 5 substituents 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 on the ring, each independently selected from the substituent group A; (b47) a quinolinyl group; (b48) a substituted quinolinyl group having 1 to 6 substituents on the ring, each independently selected from the substituent group A; (b49) a naphthyl group; (b50) a substituted naphthyl group having 1 to 7 substituents on the ring, each independently selected from the substituent group A; (b51) a triazinyl group; (b52) a substituted triazinyl group having 1 to 2 substituents on the ring, each independently selected from the substituent group A; (b53) a pyrrolyl group; (b54) a substituted pyrrolyl group having 1 to 4 substituents on the ring, each independently selected from the substituent group A; (b55) a tetrazolyl group; (b56) a substituted tetrazolyl group having one substituent on the ring, each independently selected from the substituent group A; (b57) an oxadiazonyl group; (b58) a substituted oxadiazonyl group having one substituent independently selected from the substituent group A on the ring; (b59) a 2-oxopyridyl group; (b60) a substituted 2-oxopyridyl group having one to four substituents independently selected from the substituent group A on the ring; (b61) a benzofuranyl group; (b62) a substituted benzofuranyl group having one to five substituents independently selected from the substituent group A on the ring; (b63) a benzoisoxazolyl group; (b64) a substituted benzoisoxazolyl group having one to four substituents independently selected from the substituent group A on the ring;(b65) a benzothienyl group; (b66) a substituted benzothienyl group having 1 to 5 substituents each independently selected from the substituent group A on the ring; (b67) a benzoisothiazolyl group; (b68) a substituted benzoisothiazolyl group having 1 to 4 substituents each independently selected from the substituent group A on the ring; (b69) an indolyl group; (b70) a substituted indolyl group having 1 to 6 substituents each independently selected from the substituent group A on the ring; (b71) an isoindolyl group; (b72) a substituted isoindolyl group having 1 to 6 substituents each independently selected from the substituent group A on the ring; (b73) an indazolyl group; (b74) a substituted indazolyl group having 1 to 5 substituents each independently selected from the substituent group A on the ring; (b75) a benzotriazolyl group; (b76) A substituted benzotriazolyl group having 1 to 4 substituents on the ring, each independently selected from the substituent group A; (b77) a furopyridyl group; (b78) a substituted furopyridyl group having 1 to 4 substituents on the ring, each independently selected from the substituent group A; (b79) a thienopyridyl group; (b80) a substituted thienopyridyl group having 1 to 4 substituents on the ring, each independently selected from the substituent group A; (b81) an indolizinyl group; (b82) a substituted indolizinyl group having 1 to 6 substituents on the ring, each independently selected from the substituent group A; (b83) a pyrrolopyridyl group; (b84) a substituted pyrrolopyridyl group having 1 to 5 substituents on the ring, each independently selected from the substituent group A; (b85) a pyrrolopyrimidinyl group; (b86) a substituted pyrrolopyrimidinyl group having 1 to 5 substituents each independently selected from the substituent group A on the ring; (b87) an oxazolopyridyl group; (b88) a substituted oxazolopyridyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (b89) an isoxazolopyridyl group; (b90) a substituted isoxazolopyridyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (b91) an isothiazolopyridyl group; (b92) a substituted isothiazolopyridyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (b93) an imidazopyrimidinyl group;(b94) a substituted imidazopyrimidinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b95) a pyrazolopyridyl group; (b96) a substituted pyrazolopyridyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b97) a pyrazolopyrimidinyl group; (b98) a substituted pyrazolopyrimidinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b99) a triazolopyridyl group; (b100) a substituted triazolopyridyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b101) a triazolopyrimidinyl group; (b102) a substituted triazolopyrimidinyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b103) an isoquinolinyl group; (b104) a substituted isoquinolinyl group having 1 to 6 substituents independently selected from the substituent group A on the ring; (b105) a cinnolinyl group; (b106) a substituted cinnolinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b107) a phthalazinyl group; (b108) a substituted phthalazinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b109) a quinazolinyl group; (b110) a substituted quinazolinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b111) a naphthyridinyl group; or (b112) a substituted naphthyridinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring;

[13] R 1 is (a1) a hydrogen atom; (a2) a (C1-C6) alkyl group; or (a4) a (C2-C6) alkynyl group; R 2(b5) a phenyl group; (b6) a substituted phenyl group having 1 to 5 substituents each independently selected from the substituent group A on the ring; (b7) a pyridyl group; (b8) a substituted pyridyl group having 1 to 4 substituents each independently selected from the substituent group A on the ring; (b9) a pyridazinyl group; (b10) a substituted pyridazinyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (b11) a pyrimidinyl group; (b12) a substituted pyrimidinyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (b13) a pyrazinyl group; (b14) a substituted pyrazinyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (b15) a furyl group; (b16) a substituted furyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (b17) a thienyl group; (b18) a substituted thienyl group having one to three substituents independently selected from the substituent group A on the ring; (b19) an isoxazolyl group; (b20) a substituted isoxazolyl group having one to two substituents independently selected from the substituent group A on the ring; (b21) an oxazolyl group; (b22) a substituted oxazolyl group having one to two substituents independently selected from the substituent group A on the ring; (b23) a pyrazolyl group; (b24) a substituted pyrazolyl group having one to three substituents independently selected from the substituent group A on the ring; (b25) an imidazolyl group; (b26) a substituted imidazolyl group having one to three substituents independently selected from the substituent group A on the ring; (b27) a triazolyl group; (b28) a substituted triazolyl group having on the ring one or two substituents each independently selected from the substituent group A; (b29) a thiazolyl group; (b30) a substituted thiazolyl group having on the ring one or two substituents each independently selected from the substituent group A; (b31) an isothiazolyl group; (b32) a substituted isothiazolyl group having on the ring one or two substituents each independently selected from the substituent group A; (b33) a thiadiazolyl group; (b34) a substituted thiadiazolyl group having on the ring one substituent each independently selected from the substituent group A; (b35) an imidazopyridyl group;(b36) a substituted imidazopyridyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b37) a quinoxalinyl group; (b38) a substituted quinoxalinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b39) a benzoxazolyl group; (b40) a substituted benzoxazolyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b41) a benzimidazolyl group; (b42) a substituted benzimidazolyl group having 1 to 5 substituents 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 quinolinyl group; or (b48) a substituted quinolinyl 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; (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 halo(C1-C6) alkyl group; (e17) a halo(C1-C6) alkoxy group; (e18) a halo(C3-C6) cycloalkyl group; (e19) a halo(C1-C6) alkylthio group; (e20) a halo(C1-C6) alkylsulfinyl group; (e21) a halo(C1-C6) alkylsulfonyl group; (e22). (C1-C6)alkylcarbonylamino group;(e24) (C1-C6)alkylsulfonylamino group;(e28) N-(C1-C6)alkylcarboxamide group;(e30) oxadiazolyl group;(e31) a substituted oxadiazolyl group having on the ring one substituent independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6)alkyl group, a (C1-C6)alkoxy group, a (C3-C6)cycloalkyl group, a (C1-C6)alkylthio group, a (C1-C6)alkylsulfinyl group, a (C1-C6)alkylsulfonyl group, a halo(C1-C6)alkyl group and a halo(C1-C6)alkoxy group;(e32) a (C1-C6)alkoxycarbonyl group;(e33) a methylenedioxy group which may be substituted by one or two substituents selected from the group consisting of halogen atoms, phenyl groups and (C1-C6) alkyl groups, formed by two adjacent substituents taken together; (e34) an N-(C1-C6) alkylaminosulfonyl group; (e35) an N,N-di(C1-C6) alkylaminosulfonyl group; (e36) R 6 -(R 7 -N=)O=S group (in the formula, R 6 represents a (C1-C6) alkyl group, a (C3-C6) cycloalkyl group, a halo(C1-C6) alkyl group, or a (C1-C6) alkoxy(C1-C6) alkyl group; R 7represents a hydrogen atom, a cyano group, a (C1-C6)alkyl group, a (C3-C6)cycloalkyl group, a halo(C1-C6)alkyl group, a (C2-C6)alkylcarbonyl group, or a halo(C2-C6)alkylcarbonyl group; and (e37) the compound according to

[11] or

[12] or a salt thereof, which is a substituted (C3-C6)cycloalkyl group having 1 to 3 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6)alkyl group, a (C1-C6)alkoxy group, and a (C1-C6)alkylcarbonyl group;

[14] R 1 (a1) is a hydrogen atom; R 2(b5) a phenyl group; (b6) a substituted phenyl group having 1 to 5 substituents each independently selected from the substituent group A on the ring; (b7) a pyridyl group; (b8) a substituted pyridyl group having 1 to 4 substituents each independently selected from the substituent group A on the ring; (b9) a pyridazinyl group; (b10) a substituted pyridazinyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (b11) a pyrimidinyl group; (b12) a substituted pyrimidinyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (b13) a pyrazinyl group; (b14) a substituted pyrazinyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (b23) a pyrazolyl group; (b24). a substituted pyrazolyl group having one to three substituents independently selected from the substituent group A on the ring; (b27) a triazolyl group; (b28) a substituted triazolyl group having one to two substituents independently selected from the substituent group A on the ring; (b29) a thiazolyl group; (b30) a substituted thiazolyl group having one to two substituents independently selected from the substituent group A on the ring; (b33) a thiadiazolyl group; (b34) a substituted thiadiazolyl group having one substituent independently selected from the substituent group A on the ring; (b43) a benzothiazolyl group; (b44) a substituted benzothiazolyl group having one to four substituents independently selected from the substituent group A on the ring; (b45) a thiazolopyridyl group; (b46) a substituted thiazolopyridyl group having one to four substituents independently selected from the substituent group A on the ring; (b47) a quinolinyl group; or (b48) a substituted quinolinyl 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 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). The compound or salt thereof according to any one of

[11] to

[13] , which is composed of an N,N-di(C1-C6)alkylaminosulfonyl group;

[0008]

[15] General formula (3A) [ka] {where, R 1 (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 halo(C1-C6) alkyl group; (a8) a (C1-C6) alkylcarbonyl group; (a9) a (C1-C6) alkoxycarbonyl group; (a10) a substituted (C1-C6) alkyl group having one to three substituents on the chain independently selected from the group consisting of a cyano group, a (C1-C6) alkoxy group and a (C3-C6) cycloalkyl group; (a11) a thiazolylmethyl group; (a12) (a13) a benzyl group; or (a14) a substituted benzyl group having on the ring one to three substituents independently selected from the group consisting of a halogen atom, a (C1-C6) alkyl group, and a (C1-C6) alkoxy group. R 2represents (b1) an aryl group; (b2) a substituted aryl group having on the ring one or more substituents independently selected from Substituent group A; (b3) a 5- to 10-membered heterocyclic group; or (b4) a substituted 5- to 10-membered heterocyclic group having on the ring one or more substituents independently selected from Substituent group A. However, R 2 is a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkylsulfonyl group, an N-(C1-C6) alkylaminosulfonyl group, an N,N-di(C1-C6) alkylaminosulfonyl group, or a R 6 -(R 7 -N=)O=S group (in the formula, R 6 represents a (C1-C6) alkyl group, a (C3-C6) cycloalkyl group, a halo(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 halo(C1-C6)alkyl group, a (C2-C6)alkylcarbonyl group, or a halo(C2-C6)alkylcarbonyl group. ) is not substituted. R 5 represents (i1) a (C1-C6) alkyl group; or (i2) a (C1-C6) alkoxy(C1-C6) alkyl 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 halo(C1-C6) alkyl group; (e15) a halo(C2-C6) alkenyl group; (e16) a halo(C2-C6) alkynyl group; (e17). Halo(C1-C6)alkoxy group;(e18) halo(C3-C6)cycloalkyl group;(e19) halo(C1-C6)alkylthio group;(e20) halo(C1-C6)alkylsulfinyl group;(e21) halo(C1-C6)alkylsulfonyl group;(e22) (C1-C6)alkylcarbonylamino group;(e23) halo(C1-C6)alkylcarbonylamino group;(e24) (C1-C6)alkylsulfonylamino group;(e25) halo(C1-C6)alkylsulfonylamino group;(e26) SF5 group;(e27) (C1-C6)alkoxy(C1-C6)alkyl group;(e28) N-(C1-C6)alkylcarboxamide group;(e29) an N-halo(C1-C6)alkylcarboxamide group; (e30) an oxadiazolyl group; (e31) a substituted oxadiazolyl group having on the ring one substituent independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6)alkyl group, a (C1-C6)alkoxy group, a (C3-C6)cycloalkyl group, a (C1-C6)alkylthio group, a (C1-C6)alkylsulfinyl group, a (C1-C6)alkylsulfonyl group, a halo(C1-C6)alkyl group and a halo(C1-C6)alkoxy group; (e32) a (C1-C6)alkoxycarbonyl group; (e33) a methylenedioxy group which may be substituted by one or two substituents selected from the group consisting of a halogen atom, a phenyl group and a (C1-C6)alkyl group, formed together by two adjacent substituents; (e34) an N-(C1-C6)alkylaminosulfonyl group;(e35) N,N-di(C1-C6)alkylaminosulfonyl group (e36) R; 6 -(R 7 -N=)O=S group (in the formula, R 6 represents a (C1-C6) alkyl group, a (C3-C6) cycloalkyl group, a halo(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 halo(C1-C6) alkyl group, a (C2-C6) alkylcarbonyl group, or a halo(C2-C6) alkylcarbonyl group; and (e37) a substituted (C3-C6) cycloalkyl group having 1 to 3 substituents on the ring independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, and a (C1-C6) alkylcarbonyl group.} and salts thereof,

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

[15] , R 2(b5) a phenyl group; (b6) a substituted phenyl group having 1 to 5 substituents each independently selected from the substituent group A on the ring; (b7) a pyridyl group; (b8) a substituted pyridyl group having 1 to 4 substituents each independently selected from the substituent group A on the ring; (b9) a pyridazinyl group; (b10) a substituted pyridazinyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (b11) a pyrimidinyl group; (b12) a substituted pyrimidinyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (b13) a pyrazinyl group; (b14) a substituted pyrazinyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (b15) a furyl group; (b16) a substituted furyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (b17) a thienyl group; (b18) a substituted thienyl group having one to three substituents independently selected from the substituent group A on the ring; (b19) an isoxazolyl group; (b20) a substituted isoxazolyl group having one to two substituents independently selected from the substituent group A on the ring; (b21) an oxazolyl group; (b22) a substituted oxazolyl group having one to two substituents independently selected from the substituent group A on the ring; (b23) a pyrazolyl group; (b24) a substituted pyrazolyl group having one to three substituents independently selected from the substituent group A on the ring; (b25) an imidazolyl group; (b26) a substituted imidazolyl group having one to three substituents independently selected from the substituent group A on the ring; (b27) a triazolyl group; (b28) a substituted triazolyl group having on the ring one or two substituents each independently selected from the substituent group A; (b29) a thiazolyl group; (b30) a substituted thiazolyl group having on the ring one or two substituents each independently selected from the substituent group A; (b31) an isothiazolyl group; (b32) a substituted isothiazolyl group having on the ring one or two substituents each independently selected from the substituent group A; (b33) a thiadiazolyl group; (b34) a substituted thiadiazolyl group having on the ring one substituent each independently selected from the substituent group A; (b35) an imidazopyridyl group;(b36) a substituted imidazopyridyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b37) a quinoxalinyl group; (b38) a substituted quinoxalinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b39) a benzoxazolyl group; (b40) a substituted benzoxazolyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b41) a benzimidazolyl group; (b42) a substituted benzimidazolyl group having 1 to 5 substituents 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 thiazolopyridyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b47) a quinolinyl group; (b48) a substituted quinolinyl group having 1 to 6 substituents independently selected from the substituent group A on the ring; (b49) a naphthyl group; (b50) a substituted naphthyl group having 1 to 7 substituents independently selected from the substituent group A on the ring; (b51) a triazinyl group; (b52) a substituted triazinyl group having 1 to 2 substituents independently selected from the substituent group A on the ring; (b53) a pyrrolyl group; (b54) a substituted pyrrolyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b55) a tetrazolyl group; (b56) a substituted tetrazolyl group having 1 substituent independently selected from the substituent group A on the ring; (b57) an oxadiazonyl group; (b58) a substituted oxadiazonyl group having one substituent independently selected from the substituent group A on the ring; (b59) a 2-oxopyridyl group; (b60) a substituted 2-oxopyridyl group having one to four substituents independently selected from the substituent group A on the ring; (b61) a benzofuranyl group; (b62) a substituted benzofuranyl group having one to five substituents independently selected from the substituent group A on the ring; (b63) a benzoisoxazolyl group; (b64) a substituted benzoisoxazolyl group having one to four substituents independently selected from the substituent group A on the ring;(b65) a benzothienyl group; (b66) a substituted benzothienyl group having 1 to 5 substituents each independently selected from the substituent group A on the ring; (b67) a benzoisothiazolyl group; (b68) a substituted benzoisothiazolyl group having 1 to 4 substituents each independently selected from the substituent group A on the ring; (b69) an indolyl group; (b70) a substituted indolyl group having 1 to 6 substituents each independently selected from the substituent group A on the ring; (b71) an isoindolyl group; (b72) a substituted isoindolyl group having 1 to 6 substituents each independently selected from the substituent group A on the ring; (b73) an indazolyl group; (b74) a substituted indazolyl group having 1 to 5 substituents each independently selected from the substituent group A on the ring; (b75) a benzotriazolyl group; (b76) A substituted benzotriazolyl group having 1 to 4 substituents on the ring, each independently selected from the substituent group A; (b77) a furopyridyl group; (b78) a substituted furopyridyl group having 1 to 4 substituents on the ring, each independently selected from the substituent group A; (b79) a thienopyridyl group; (b80) a substituted thienopyridyl group having 1 to 4 substituents on the ring, each independently selected from the substituent group A; (b81) an indolizinyl group; (b82) a substituted indolizinyl group having 1 to 6 substituents on the ring, each independently selected from the substituent group A; (b83) a pyrrolopyridyl group; (b84) a substituted pyrrolopyridyl group having 1 to 5 substituents on the ring, each independently selected from the substituent group A; (b85) a pyrrolopyrimidinyl group; (b86) a substituted pyrrolopyrimidinyl group having 1 to 5 substituents each independently selected from the substituent group A on the ring; (b87) an oxazolopyridyl group; (b88) a substituted oxazolopyridyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (b89) an isoxazolopyridyl group; (b90) a substituted isoxazolopyridyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (b91) an isothiazolopyridyl group; (b92) a substituted isothiazolopyridyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (b93) an imidazopyrimidinyl group;(b94) a substituted imidazopyrimidinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b95) a pyrazolopyridyl group; (b96) a substituted pyrazolopyridyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b97) a pyrazolopyrimidinyl group; (b98) a substituted pyrazolopyrimidinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b99) a triazolopyridyl group; (b100) a substituted triazolopyridyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b101) a triazolopyrimidinyl group; (b102) a substituted triazolopyrimidinyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b103) an isoquinolinyl group; (b104) a substituted isoquinolinyl group having 1 to 6 substituents independently selected from the substituent group A on the ring; (b105) a cinnolinyl group; (b106) a substituted cinnolinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b107) a phthalazinyl group; (b108) a substituted phthalazinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b109) a quinazolinyl group; (b110) a substituted quinazolinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b111) a naphthyridinyl group; or (b112) a substituted naphthyridinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring;

[17] R 1 is (a1) a hydrogen atom; (a2) a (C1-C6) alkyl group; or (a4) a (C2-C6) alkynyl group; R 2(b5) a phenyl group; (b6) a substituted phenyl group having 1 to 5 substituents each independently selected from the substituent group A on the ring; (b7) a pyridyl group; (b8) a substituted pyridyl group having 1 to 4 substituents each independently selected from the substituent group A on the ring; (b9) a pyridazinyl group; (b10) a substituted pyridazinyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (b11) a pyrimidinyl group; (b12) a substituted pyrimidinyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (b13) a pyrazinyl group; (b14) a substituted pyrazinyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (b15) a furyl group; (b16) a substituted furyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (b17) a thienyl group; (b18) a substituted thienyl group having one to three substituents independently selected from the substituent group A on the ring; (b19) an isoxazolyl group; (b20) a substituted isoxazolyl group having one to two substituents independently selected from the substituent group A on the ring; (b21) an oxazolyl group; (b22) a substituted oxazolyl group having one to two substituents independently selected from the substituent group A on the ring; (b23) a pyrazolyl group; (b24) a substituted pyrazolyl group having one to three substituents independently selected from the substituent group A on the ring; (b25) an imidazolyl group; (b26) a substituted imidazolyl group having one to three substituents independently selected from the substituent group A on the ring; (b27) a triazolyl group; (b28) a substituted triazolyl group having on the ring one or two substituents each independently selected from the substituent group A; (b29) a thiazolyl group; (b30) a substituted thiazolyl group having on the ring one or two substituents each independently selected from the substituent group A; (b31) an isothiazolyl group; (b32) a substituted isothiazolyl group having on the ring one or two substituents each independently selected from the substituent group A; (b33) a thiadiazolyl group; (b34) a substituted thiadiazolyl group having on the ring one substituent each independently selected from the substituent group A; (b35) an imidazopyridyl group;(b36) a substituted imidazopyridyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b37) a quinoxalinyl group; (b38) a substituted quinoxalinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b39) a benzoxazolyl group; (b40) a substituted benzoxazolyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b41) a benzimidazolyl group; (b42) a substituted benzimidazolyl group having 1 to 5 substituents 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 quinolinyl group; or (b48) a substituted quinolinyl 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; or (i2) a (C1-C6)alkoxy(C1-C6)alkyl group; 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 halo(C1-C6) alkyl group; (e17) a halo(C1-C6) alkoxy group; (e18) a halo(C3-C6) cycloalkyl group; (e19) a halo(C1-C6) alkylthio group; (e20) a halo(C1-C6) alkylsulfinyl group; (e21) a halo(C1-C6) alkylsulfonyl group; (e22). (C1-C6)alkylcarbonylamino group;(e24) (C1-C6)alkylsulfonylamino group;(e28) N-(C1-C6)alkylcarboxamide group;(e30) oxadiazolyl group;(e31) a substituted oxadiazolyl group having on the ring one substituent independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6)alkyl group, a (C1-C6)alkoxy group, a (C3-C6)cycloalkyl group, a (C1-C6)alkylthio group, a (C1-C6)alkylsulfinyl group, a (C1-C6)alkylsulfonyl group, a halo(C1-C6)alkyl group and a halo(C1-C6)alkoxy group;(e32) a (C1-C6)alkoxycarbonyl group;(e33) a methylenedioxy group which may be substituted by one or two substituents selected from the group consisting of halogen atoms, phenyl groups and (C1-C6) alkyl groups, formed by two adjacent substituents taken together; (e34) an N-(C1-C6) alkylaminosulfonyl group; (e35) an N,N-di(C1-C6) alkylaminosulfonyl group; (e36) R 6 -(R 7 -N=)O=S group (in the formula, R 6 represents a (C1-C6) alkyl group, a (C3-C6) cycloalkyl group, a halo(C1-C6) alkyl group, or a (C1-C6) alkoxy(C1-C6) alkyl group; R 7represents a hydrogen atom, a cyano group, a (C1-C6)alkyl group, a (C3-C6)cycloalkyl group, a halo(C1-C6)alkyl group, a (C2-C6)alkylcarbonyl group, or a halo(C2-C6)alkylcarbonyl group; and (e37) the compound according to

[15] or

[16] or a salt thereof, which is a substituted (C3-C6)cycloalkyl group having 1 to 3 substituents on the ring, each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6)alkyl group, a (C1-C6)alkoxy group, and a (C1-C6)alkylcarbonyl group;

[18] R 1 (a1) is a hydrogen atom; R 2(b5) a phenyl group; (b6) a substituted phenyl group having 1 to 5 substituents each independently selected from the substituent group A on the ring; (b7) a pyridyl group; (b8) a substituted pyridyl group having 1 to 4 substituents each independently selected from the substituent group A on the ring; (b9) a pyridazinyl group; (b10) a substituted pyridazinyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (b11) a pyrimidinyl group; (b12) a substituted pyrimidinyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (b13) a pyrazinyl group; (b14) a substituted pyrazinyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (b23) a pyrazolyl group; (b24). a substituted pyrazolyl group having one to three substituents independently selected from the substituent group A on the ring; (b27) a triazolyl group; (b28) a substituted triazolyl group having one to two substituents independently selected from the substituent group A on the ring; (b29) a thiazolyl group; (b30) a substituted thiazolyl group having one to two substituents independently selected from the substituent group A on the ring; (b33) a thiadiazolyl group; (b34) a substituted thiadiazolyl group having one substituent independently selected from the substituent group A on the ring; (b43) a benzothiazolyl group; (b44) a substituted benzothiazolyl group having one to four substituents independently selected from the substituent group A on the ring; (b45) a thiazolopyridyl group; (b46) a substituted thiazolopyridyl group having one to four substituents independently selected from the substituent group A on the ring; (b47) a quinolinyl group; or (b48) a substituted quinolinyl 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 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). The compound or salt thereof according to any one of

[15] to

[17] , which is composed of an N,N-di(C1-C6)alkylaminosulfonyl group; Regarding. Effect of the Invention

[0009] The compound or salt thereof of the present invention has an excellent effect as an insecticide, and is effective not only against pests in the agricultural and horticultural fields, but also against pests that parasitize pet animals such as dogs and cats, and livestock such as cows and sheep. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0010] In the definitions of the general formulae (1), (13A), and (3A) of the compounds of the present invention, "halo" means a "halogen atom" and represents a chlorine atom, a bromine atom, an iodine atom, or a fluorine atom.

[0011] The term "(C1-C6) alkyl group" refers to a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms, such as a methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, isobutyl group, secondary butyl group, tertiary butyl group, normal pentyl group, isopentyl group, tertiary pentyl group, neopentyl group, 2,3-dimethylpropyl group, 1-ethylpropyl group, 1-methylbutyl group, 2-methylbutyl group, normal hexyl group, isohexyl group, 2-hexyl group, 3-hexyl group, 2-methylpentyl group, 3-methylpentyl group, 1,1,2-trimethylpropyl group, or 3,3-dimethylbutyl group.

[0012] The term "(C2-C6) alkenyl group" refers to a linear or branched alkenyl group having 2 to 6 carbon atoms, such as a vinyl group, an allyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 2-methyl-2-propenyl group, a 1-methyl-2-propenyl group, a 2-methyl-1-propenyl group, a pentenyl group, a 1-hexenyl group, or a 3,3-dimethyl-1-butenyl group. The term "6) alkynyl group" refers to a straight-chain or branched-chain alkynyl group having 2 to 6 carbon atoms, such as an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 3-methyl-1-propynyl group, a 2-methyl-3-propynyl group, a pentynyl group, a 1-hexynyl group, a 3-methyl-1-butynyl group, or a 3,3-dimethyl-1-butynyl group.

[0013] The "(C3-C6) cycloalkyl group" refers to a cyclic alkyl group having 3 to 6 carbon atoms, such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, and the "(C1-C6) alkoxy group" refers to a straight-chain or branched-chain alkoxy group having 1 to 6 carbon atoms, such as a methoxy group, an ethoxy group, a normal propoxy group, an isopropoxy group, a normal butoxy group, a secondary butoxy group, a tertiary butoxy group, a normal pentyloxy group, an isopentyloxy group, a tertiary pentyloxy group, a neopentyloxy group, a 2,3-dimethylpropyloxy group, a 1-ethylpropyloxy group, a 1-methylbutyloxy group, a normal hexyloxy group, an isohexyloxy group, or a 1,1,2-trimethylpropyloxy group.

[0014] The "(C1-C6) alkylthio group" refers to a straight-chain or branched-chain alkylthio group having 1 to 6 carbon atoms, such as a methylthio group, an ethylthio group, a normal propylthio group, an isopropylthio group, a normal butylthio group, a secondary butylthio group, a tertiary butylthio group, a normal pentylthio group, an isopentylthio group, a tertiary pentylthio group, a neopentylthio group, a 2,3-dimethylpropylthio group, a 1-ethylpropylthio group, a 1-methylbutylthio group, a normal hexylthio group, an isohexylthio group, or a 1,1,2-trimethylpropylthio group.

[0015] The "(C1-C6)alkylsulfinyl group" refers to a linear or branched alkylsulfinyl group having 1 to 6 carbon atoms, such as a methylsulfinyl group, ethylsulfinyl group, normal propylsulfinyl group, isopropylsulfinyl group, normal butylsulfinyl group, secondary butylsulfinyl group, tertiary butylsulfinyl group, normal pentylsulfinyl group, isopentylsulfinyl group, tertiary pentylsulfinyl group, neopentylsulfinyl group, 2,3-dimethylpropylsulfinyl group, 1-ethylpropylsulfinyl group, 1-methylbutylsulfinyl group, normal hexylsulfinyl group, isohexylsulfinyl group, or 1,1,2-trimethylpropylsulfinyl group.

[0016] Examples of the "(C1-C6) alkylsulfonyl group" include linear or branched alkylsulfonyl groups having 1 to 6 carbon atoms, such as a methylsulfonyl group, ethylsulfonyl group, normal propylsulfonyl group, isopropylsulfonyl group, normal butylsulfonyl group, secondary butylsulfonyl group, tertiary butylsulfonyl group, normal pentylsulfonyl group, isopentylsulfonyl group, tertiary pentylsulfonyl group, neopentylsulfonyl group, 2,3-dimethylpropylsulfonyl group, 1-ethylpropylsulfonyl group, 1-methylbutylsulfonyl group, normal hexylsulfonyl group, isohexylsulfonyl group, and 1,1,2-trimethylpropylsulfonyl group.

[0017] The "(C1-C6)alkylcarbonyl group" refers to an alkylcarbonyl group having 2 to 7 carbon atoms, such as an acetyl group, a propanoyl group, a butanoyl group, a 2-methylpropanoyl group, a pentanoyl group, a 2-methylbutanoyl group, a 3-methylbutanoyl group, a pivaloyl group, or a hexanoyl group, which has the above-mentioned (C1-C6)alkyl group.

[0018] The "(C1-C6)alkylcarbonylamino group" refers to an alkylcarbonylamino group having 2 to 7 carbon atoms, such as an alkylcarbonylamino group having the above-mentioned (C1-C6) alkyl group, such as an acetylamino group, a propanoylamino group, a butanoylamino group, a 2-methylpropanoylamino group, a pentanoylamino group, a 2-methylbutanoylamino group, a 3-methylbutanoylamino group, a pivaloylamino group, or a hexanoylamino group.

[0019] Examples of the "(C1-C6) alkylsulfonylamino group" include linear or branched alkylsulfonylamino groups having 1 to 6 carbon atoms, such as methylsulfonylamino group, ethylsulfonylamino group, normal propylsulfonylamino group, isopropylsulfonylamino group, normal butylsulfonylamino group, secondary butylsulfonylamino group, tertiary butylsulfonylamino group, normal pentylsulfonylamino group, isopentylsulfonylamino group, tertiary pentylsulfonylamino group, neopentylsulfonylamino group, 2,3-dimethylpropylsulfonylamino group, 1-ethylpropylsulfonylamino group, 1-methylbutylsulfonylamino group, normal hexylsulfonylamino group, isohexylsulfonylamino group, and 1,1,2-trimethylpropylsulfonylamino group.

[0020] The "N-(C1-C6)alkylcarboxamide group" refers to an alkylcarboxamide group having 2 to 7 carbon atoms and having a linear or branched alkyl group having 1 to 6 carbon atoms, such as an N-methylcarboxamide group, an N-ethylcarboxamide group, an N-normal propylcarboxamide group, an N-isopropylcarboxamide group, an N-normal butylcarboxamide group, an N-isobutylcarboxamide group, an N-secondary butylcarboxamide group, an N-tertiary butylcarboxamide group, an N-normal pentylcarboxamide group, an N-isopentylcarboxamide group, an N-tertiary pentylcarboxamide group, an N-neopenthicarboxamide group, an N-normal hexylcarboxamide group, or an N-isohexylcarboxamide group.

[0021] The "(C1-C6)alkoxycarbonyl group" refers to an alkoxycarbonyl group having 2 to 7 carbon atoms, such as an alkoxycarbonyl group having the above-mentioned (C1-C6) alkoxy group, such as a methoxycarbonyl group, ethoxycarbonyl group, normal propoxycarbonyl group, isopropoxycarbonyl group, normal butoxycarbonyl group, isobutoxycarbonyl group, secondary butoxycarbonyl group, tertiary butoxycarbonyl group, or pentyloxycarbonyl group.

[0022] Examples of the "N-(C1-C6) alkylsulfamoyl group" include an N-methylsulfamoyl group, an N-ethylsulfamoyl group, an N-normal propylsulfamoyl group, an N-isopropylsulfamoyl group, an N-normal butylsulfamoyl group, an N-isobutylsulfamoyl group, an N-secondary butylsulfamoyl group, an N-tertiary butylsulfamoyl group, an N-normal pentylsulfamoyl group, an N-isopentylsulfamoyl group, an N-tertiary pentylsulfamoyl group, an N-neopentylsulfamoyl group, an N-(2,3-dimethylpropyl)sulfamoyl group, an N-methylsulfamoyl group, an N-ethylsulfamoyl group, an N-normal propylsulfamoyl group, an N-isopropylsulfamoyl group, an N-normal butylsulfamoyl group, an N-isobutylsulfamoyl group, an N-secondary butylsulfamoyl group, an N-tertiary butylsulfamoyl group, an N-normal pentylsulfamoyl group, an N-tertiary pentylsulfamoyl group, an N-neopentylsulfamoyl group, an N-(2,3-dimethylpropyl)sulfamoyl group, an N-methylsulfamoyl group, an N-ethylsulfamoyl group, an N-methyl ... and N-alkylsulfamoyl groups having 1 to 6 carbon atoms, such as an N-alkyl group having 1 to 6 carbon atoms, such as an N-alkyl group, an N-(1-ethylpropyl)sulfamoyl group, an N-(1-methylbutyl)sulfamoyl group, an N-(2-methylbutyl)sulfamoyl group, an N-normal hexylsulfamoyl group, an N-isohexylsulfamoyl group, an N-(2-hexyl)sulfamoyl group, an N-(3-hexyl)famoyl group, an N-(2-methylpentyl)famoyl group, an N-(3-methylpentyl)sulfamoyl group, an N-(1,1,2-trimethylpropyl)sulfamoyl group, or an N-(3,3-dimethylbutyl)sulfamoyl group.

[0023] Examples of the "N-(C1-C6) alkylaminosulfonyl group" include linear or branched alkylaminosulfonyl groups having 1 to 6 carbon atoms, such as an N-methylaminosulfonyl group, an N-ethylaminosulfonyl group, an N-normal propylaminosulfonyl group, an N-isopropylaminosulfonyl group, an N-normal butylaminosulfonyl group, an N-secondary butylaminosulfonyl group, an N-tertiary butylaminosulfonyl group, an N-normal pentylaminosulfonyl group, an N-isopentylaminosulfonyl group, an N-tertiary pentylaminosulfonyl group, an N-neopentylaminosulfonyl group, an N-(2,3-dimethylpropyl)aminosulfonyl group, an N-(1-ethylpropyl)aminosulfonyl group, an N-(1-methylbutyl)aminosulfonyl group, an N-normal hexylaminosulfonyl group, an N-isohexylaminosulfonyl group, or an N-(1,1,2-trimethylpropyl)aminosulfonyl group.

[0024] Examples of the "N,N-di(C1-C6)alkylaminosulfonyl group" include an N,N-dimethylaminosulfonyl group, an N,N-diethylaminosulfonyl group, an N,N-dinormalpropylaminosulfonyl group, an N,N-diisopropylaminosulfonyl group, an N,N-dinormalbutylaminosulfonyl group, an N,N-disecondarybutylaminosulfonyl group, an N,N-ditertiarybutylaminosulfonyl group, an N-methyl-N-ethylaminosulfonyl group, an N-methyl-N-normalpropylaminosulfonyl group, an N-methyl-N-isopropylaminosulfonyl group, an N-methyl-N-normalbutylaminosulfonyl group, an N-methyl-N-secondarybutylaminosulfonyl group, an N-methyl-N- ...tertiarybutylaminosulfonyl group, an N-methyl-N-tertiarybutylaminosulfonyl group, an N-methyl-N-tertiarybutylaminosulfon

[0043] This refers to a straight-chain or branched-chain dialkylaminosulfonyl group having 1 to 6 carbon atoms, such as an N-methyl-N-normal pentylaminosulfonyl group, an N-methyl-N-isopentylaminosulfonyl group, an N-methyl-N-tertiary pentylaminosulfonyl group, an N-methyl-N-neopentylaminosulfonyl group, an N-methyl-N-(2,3-dimethylpropyl)aminosulfonyl group, an N-methyl-N-(1-ethylpropyl)aminosulfonyl group, an N-methyl-N-(1-methylbutyl)aminosulfonyl group, an N-methyl-N-normal hexylaminosulfonyl group, an N-methyl-N-isohexylaminosulfonyl group, or an N-methyl-N-(1,1,2-trimethylpropyl)aminosulfonyl group.

[0025] The above-mentioned "(C1-C6) alkyl group", "(C2-C6) alkenyl group", "(C2-C6) alkynyl group", "(C1-C6) alkoxy group", "(C1-C6) alkylthio group", "(C1-C6) alkylsulfinyl group", "(C1-C6) alkylsulfonyl group", "(C3-C6) cycloalkyl group", "(C1-C6) alkylcarbonylamino group", "(C1-C6) alkylsulfonylamino group", "N-(C1-C6) alkylcarboxamide group" and the like may be substituted with one or more halogen atoms at substitutable positions, and when there are two or more halogen atoms substituted, the halogen atoms may be the same or different.

[0026] They are respectively represented as "halo(C1-C6)alkyl groups", "halo(C2-C6)alkenyl groups", "halo(C2-C6)alkynyl groups", "halo(C1-C6)alkoxy groups", "halo(C1-C6)alkylthio groups", "halo(C1-C6)alkylsulfinyl groups", "halo(C1-C6)alkylsulfonyl groups", "halo(C3-C6)cycloalkyl groups", "halo(C1-C6)alkylcarbonylamino groups", "halo(C1-C6)alkylsulfonylamino groups", "N-halo(C1-C6)alkylcarboxamide groups", etc.

[0027] Expressions such as "(C1-C6)", "(C2-C6)", "(C3-C6)" indicate the range of carbon atoms of various substituents. Furthermore, the above definitions can be applied to the groups to which the above substituents are linked, for example, "(C1-C6)alkoxy(C1-C6)alkyl group" indicates that a linear or branched alkoxy group having 1 to 6 carbon atoms is linked to a linear or branched alkyl group having 1 to 6 carbon atoms.

[0028] The term "aryl group" refers to an aromatic hydrocarbon group having 6 to 10 carbon atoms, such as a phenyl group, a 1-naphthyl group, or a 2-naphthyl group.

[0029] Examples of the "5- to 10-membered heterocyclic group" include a 5- or 6-membered monocyclic aromatic heterocyclic group containing, as a ring-constituting atom other than carbon atoms, 1 to 4 heteroatoms selected from oxygen atoms, sulfur atoms, and nitrogen atoms, an aromatic fused heterocyclic group in which the monocyclic aromatic heterocyclic ring is fused with a benzene ring or a monocyclic aromatic ring, a 4- to 6-membered monocyclic non-aromatic heterocyclic group, or a non-aromatic fused heterocyclic group in which the monocyclic non-aromatic heterocyclic ring is fused 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 with an oxo group.

[0030] Examples of the "monocyclic aromatic heterocyclic group" include a furyl group, a thienyl group, a pyridyl group, a 2-oxopyridyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group (e.g., a 1,3,4-oxadiazolyl group, a 1,2,4-oxadiazolyl group), a thiadiazolyl group (e.g., a 1,3,4-thiadiazolyl group, a 1,2,4-thiadiazolyl group), a triazolyl group (e.g., a 1,2,4-triazolyl group), a tetrazolyl group, Examples of the "aromatic condensed heterocyclic group" include a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, a quinoxalinyl group, a cinnolinyl group, a phthalazinyl group, a naphthyridinyl group, a benzofuranyl group, a benzothienyl group, a benzoxazolyl group, a benzoisoxazolyl group, a benzothiazolyl group, a benzoisothiazolyl group, a benzimidazolyl group, a benzotriazolyl group, an indolyl group, an isoindolyl group, an indazolyl group, a furopyridyl group, Thienopyridyl group, pyrrolopyridyl group (e.g., pyrrolo[1,2-a]pyridyl group, pyrrolo[2,3-b]pyridyl group), oxazolopyridyl group (e.g., oxazolo[3,2-a]pyridyl group, oxazolo[5,4-b]pyridyl group, oxazolo[4,5-b]pyridyl group), isoxazolopyridyl group (e.g., isoxazolo[2,3-a]pyridyl group, isoxazolo[4,5-b]pyridyl group, isoxazolo[5,4-b]pyridyl group), thiazolopyridyl group (e.g., thiazolo[3,2-a]pyridyl group, thiazolo[5,4-b]pyridyl group), a pyridyl group, a thiazolo[4,5-b]pyridyl group), an isothiazolopyridyl group (e.g., an isothiazolo[2,3-a]pyridyl group, an isothiazolo[4,5-b]pyridyl group, an isothiazolo[5,4-b]pyridyl group), an imidazopyridyl group (e.g., an imidazo[1,2-a]pyridyl group, an imidazo[4,5-b]pyridyl group), a pyrazolopyridyl group (e.g., a pyrazolo[1,5-a]pyridyl group, a pyrazolo[3,4-a]pyridyl group, a pyrazolo[4,3-a]pyridyl group), an indolizinyl group, a triazolopyridyl group (e.g., a [1,2,4]triazolo[1,5-a]pyridyl group), triazolopyrimidinyl group, pyrrolopyrimidinyl group, pyrrolopyrazinyl group, imidazopyrimidinyl group, imidazopyrazinyl group, pyrazolopyrimidinyl group, pyrazolothienyl group, pyrazolotriazinyl group, etc.

[0031] Examples of the "monocyclic non-aromatic heterocyclic group" include an oxetanyl group, a thietanyl group, an azetidinyl group, a pyrrolidinyl group, a pyrrolidinyl-2-one group, a piperidinyl group, a morpholinyl group, a thiomorpholinyl group, a piperazinyl group, a hexamethyleneiminyl group, an oxazolidinyl group, a thiazolidinyl group, an imidazolidinyl group, an oxazolinyl group, a thiazolinyl group, an isoxazolinyl group, and an imidazolinyl group. , dioxolyl group, dioxolanyl group, dihydrooxadiazolyl group, 2-oxo-pyrrolidin-1-yl group, 2-oxopyridin-4-yl group, 2,4-dioxopyrimidin-5-yl group, 2-oxo-1,3-oxazolidin-5-yl group, 5-oxo-1,2,4-oxadiazolin-3-yl group, 1,3-dioxolan-2-yl group, 1,3-dioxan-2-yl group, 1,3-dioxepa Examples of the "non-aromatic condensed heterocyclic group" include a dihydroindolyl group, a dihydroisoindolyl group, a dihydrobenzofuranyl group, a dihydrobenzodioxinyl group, a dihydrobenzodioxepinyl group, a tetrahydrobenzofuranyl group, a chromenyl group, a dihydroquinolinyl group, a tetrahydroquinolinyl group, a dihydroisoquinolinyl group, a tetrahydroisoquinolinyl group, a dihydrophthalazinyl group, and the like.

[0032] Examples of the salts of the compounds represented by general formulae (1), (13A), and (3A) of the present invention include inorganic acid salts such as hydrochloride, sulfate, nitrate, and phosphate; organic acid salts such as acetate, fumarate, maleate, oxalate, methanesulfonate, benzenesulfonate, and paratoluenesulfonate; and salts with inorganic or organic bases such as sodium ion, potassium ion, calcium ion, and trimethylammonium.

[0033] The compounds and salts thereof represented by the general formulae (1), (13A), and (3A) of the present invention may have one or more asymmetric centers in their structural formulae, and may have two or more optical isomers and diastereomers, and the present invention includes all of the optical isomers and mixtures containing them in any ratio. The compounds and salts thereof represented by the general formulae (1), (13A), and (3A) of the present invention may have two geometric isomers derived from a carbon-carbon double bond in their structural formulae, and the present invention includes all of the geometric isomers and mixtures containing them in any ratio. The compounds and salts thereof represented by the general formulae (1), (13A), and (3A) of the present invention may have multiple tautomers, and the present invention includes all of the tautomers and mixtures containing them in any ratio.

[0034] In the compounds represented by the general formulae (1), (13A), and (3A) of the present invention, preferred embodiments are shown below. The compounds represented by the general formulae (13A) and (3A) are useful as synthetic intermediates for the compound represented by the general formula (1).

[0035] In the general formula (1), R 1 is preferably (a1) a hydrogen atom; (a2) a (C1-C6) alkyl group; or (a4) a (C2-C6) alkynyl group, (a1) A hydrogen atom is more preferred.

[0036] In the general formula (1), R 2The above are (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), (b82), (b83), (b84), (b85), (b86), (b87), (b88), (b89), (b90), (b91), (b92), (b93), (b94), (b95), (b96), (b97), (b98), (b99), (b10), (b100), (b101), (b102), (b103), (b104), (b1 2), (b33), (b34), (b35), (b36), (b37), (b38), (b39), (b40), (b41), (b42), (b43), (b44), (b45), (b4 6), (b47), (b48), (b49), (b50), (b51), (b52), (b53), (b54), (b55), (b56), (b57), (b58), (b59), (b6 0), (b61), (b62), (b63), (b64), (b65), (b66), (b67), (b68), (b69), (b70), (b71), (b72), (b73), (b7 4), (b75), (b76), (b77), (b78), (b79), (b80), (b81), (b82), (b83), (b84), (b85), (b86), (b87), (b8 8), (b89), (b90), (b91), (b92), (b93), (b94), (b95), (b96), (b97), (b98), (b99), (b100), (b101), (b102), (b103), (b104), (b105), (b106), (b107), (b108), (b109), (b110), (b111) or (b112), The above (b5), (b6), (b7), (b8), (b9), (b10), (b11), (b12), (b13), (b14), (b15), (b16), (b17), (b18), (b19), (b20), (b21), (b22), (b23), (b24), (b25), (b26), (b27), groups (b28), (b29), (b30), (b31), (b32), (b33), (b34), (b35), (b36), (b37), (b38), (b39), (b40), (b41), (b42), (b43), (b44), (b45), (b46), (b47), or (b48) are more preferred; More preferred are the groups (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).

[0037] In the general formula (1), R 3 is preferably (c1) a hydrogen atom; or (c2) (C1-C6) alkyl.

[0038] In the general formula (1), R 4 The above are (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), (d40), (d41), (d42), (d43), (d44), (d45), (d46), (d47), (d48), (d49), (d50), (d51), (d52), (d53), (d54), (d55), (d56) or (d57), The above (d1), (d2), (d3), (d4), (d5), (d8), (d9), (d12), (d13), (d14), (d15), (d16), (d17), (d18), (d19), (d20), (d21), (d22), (d24), (d25), (d26), (d27), (d32), ( More preferred are groups represented by the formula (d33), (d34), (d35), (d36), (d37), (d42), (d43), (d44), (d45), (d46), (d47), (d48), (d49), (d50), (d51), (d52), (d53), (d54), (d55), (d56), or (d57).

[0039] In the general formula (1), X is preferably an oxygen atom. In the general formula (1), Y is preferably an oxygen atom. In addition, in the general formula (1), it is also preferable that X is an oxygen atom and Y is a sulfur atom. In addition, in the general formula (1), it is also preferable that X is a sulfur atom and Y is an oxygen atom.

[0040] In general formula (1), the substituent group A preferably consists of the above-mentioned 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), More preferably, it comprises the groups (e1), (e2), (e6), (e9), (e11), (e12), (e13), (e14), (e17), (e19), (e21), (e32), (e34), and (e35) above.

[0041] In general formula (1), the substituent group B preferably consists of the above-mentioned groups (f1), (f2), (f3), (f4), (f5), (f6), (f7), (f8), (f9), (f10), and (f11). More preferably, it consists of the above groups (f1), (f2), (f3) and (f4).

[0042] In general formula (1), the substituent group C preferably consists of the above-mentioned groups (g1), (g2), (g3), (g4), (g5), (g6), (g7), (g8), (g9), (g10), (g11), (g12), (g13), (g15), and (g16). More preferably, it comprises the above groups (g1), (g2), (g13), (g15), and (g16).

[0043] In general formula (1), the substituent group D preferably consists of the above-mentioned groups (h1), (h2), (h3), (h4), (h5), (h6), (h7), (h8), (h9), (h10), (h11), (h12), (h13), (h14), (h15), (h16), (h17), (h18), (h20), (h21), (h22), and (h23), More preferably, it comprises the groups (h1), (h2), (h3), (h5), (h6), (h8), (h11), (h12), (h17), (h20), and (h21) above.

[0044] In general formula (13A), R 1 is preferably (a1) a hydrogen atom; (a2) a (C1-C6) alkyl group; or (a4) a (C2-C6) alkynyl group, (a1) A hydrogen atom is more preferred.

[0045] In general formula (13A), R 2The above are (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), (b82), (b83), (b84), (b85), (b86), (b87), (b88), (b89), (b90), (b91), (b92), (b93), (b94), (b95), (b96), (b97), (b98), (b99), (b10), (b100), (b101), (b102), (b103), (b104), (b1 2), (b33), (b34), (b35), (b36), (b37), (b38), (b39), (b40), (b41), (b42), (b43), (b44), (b45), (b4 6), (b47), (b48), (b49), (b50), (b51), (b52), (b53), (b54), (b55), (b56), (b57), (b58), (b59), (b6 0), (b61), (b62), (b63), (b64), (b65), (b66), (b67), (b68), (b69), (b70), (b71), (b72), (b73), (b7 4), (b75), (b76), (b77), (b78), (b79), (b80), (b81), (b82), (b83), (b84), (b85), (b86), (b87), (b8 8), (b89), (b90), (b91), (b92), (b93), (b94), (b95), (b96), (b97), (b98), (b99), (b100), (b101), (b102), (b103), (b104), (b105), (b106), (b107), (b108), (b109), (b110), (b111) or (b112), The above (b5), (b6), (b7), (b8), (b9), (b10), (b11), (b12), (b13), (b14), (b15), (b16), (b17), (b18), (b19), (b20), (b21), (b22), (b23), (b24), (b25), (b26), (b27), groups (b28), (b29), (b30), (b31), (b32), (b33), (b34), (b35), (b36), (b37), (b38), (b39), (b40), (b41), (b42), (b43), (b44), (b45), (b46), (b47), or (b48) are more preferred; More preferred are the groups (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).

[0046] In general formula (13A), the substituent group A preferably consists of the above-mentioned 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). More preferably, it comprises the groups (e1), (e2), (e6), (e9), (e11), (e12), (e13), (e14), (e17), (e19), (e21), (e32), (e34), and (e35) above.

[0047] In general formula (3A), R 1 is preferably (a1) a hydrogen atom; (a2) a (C1-C6) alkyl group; or (a4) a (C2-C6) alkynyl group, (a1) A hydrogen atom is more preferred.

[0048] In general formula (3A), R 2The above are (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), (b82), (b83), (b84), (b85), (b86), (b87), (b88), (b89), (b90), (b91), (b92), (b93), (b94), (b95), (b96), (b97), (b98), (b99), (b10), (b100), (b101), (b102), (b103), (b104), (b1 2), (b33), (b34), (b35), (b36), (b37), (b38), (b39), (b40), (b41), (b42), (b43), (b44), (b45), (b4 6), (b47), (b48), (b49), (b50), (b51), (b52), (b53), (b54), (b55), (b56), (b57), (b58), (b59), (b6 0), (b61), (b62), (b63), (b64), (b65), (b66), (b67), (b68), (b69), (b70), (b71), (b72), (b73), (b7 4), (b75), (b76), (b77), (b78), (b79), (b80), (b81), (b82), (b83), (b84), (b85), (b86), (b87), (b8 8), (b89), (b90), (b91), (b92), (b93), (b94), (b95), (b96), (b97), (b98), (b99), (b100), (b101), (b102), (b103), (b104), (b105), (b106), (b107), (b108), (b109), (b110), (b111) or (b112), The above (b5), (b6), (b7), (b8), (b9), (b10), (b11), (b12), (b13), (b14), (b15), (b16), (b17), (b18), (b19), (b20), (b21), (b22), (b23), (b24), (b25), (b26), (b27), groups (b28), (b29), (b30), (b31), (b32), (b33), (b34), (b35), (b36), (b37), (b38), (b39), (b40), (b41), (b42), (b43), (b44), (b45), (b46), (b47), or (b48) are more preferred; More preferred are the groups (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).

[0049] In general formula (3A), R 5 As the alkyl group, (i1) a (C1-C6) alkyl group is preferable.

[0050] In general formula (3A), the substituent group A preferably consists of the above-mentioned 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), More preferably, it comprises the groups (e1), (e2), (e6), (e9), (e11), (e12), (e13), (e14), (e17), (e19), (e21), (e32), (e34), and (e35) above.

[0051] The various compounds of the present invention can be produced, for example, by the following production methods, but the present invention is not limited to these.

[0052] Manufacturing method 1 [ka]

[0053] {where, R 2 , R 3 and R 4 is the same as above. The compound represented by general formula (1a) of the present invention can be produced from a compound represented by general formula (11) by the following steps [a], [b], [c], [d], [e] and [f].

[0054] Process [a] A process for producing a compound represented by general formula (9) by reacting a compound represented by general formula (11) with a benzophenone represented by formula (10). Process [b] A process for producing a compound represented by general formula (7) by reacting a compound represented by general formula (9) with methyl bromoacetate represented by formula (8). Process [c] A process for producing a compound represented by general formula (6) by hydrolyzing a compound represented by general formula (7). Process [d] A process for producing a compound represented by general formula (4) by condensing a compound represented by general formula (6) and a compound represented by general formula (5) through an amidation reaction. Process [e] A process for producing a compound represented by general formula (3) by carrying out a cyclization reaction from a compound represented by general formula (4). Process [f] A process for producing a compound represented by general formula (1a) of the present invention by reacting a compound represented by general formula (3) with a compound represented by general formula (2).

[0055] Manufacturing method of step [a] The compound represented by the general formula (9) can be produced by reacting the compound represented by the general formula (11) with the benzophenone represented by the formula (10) in the presence of an acid and an inert solvent.

[0056] Examples of the acid used in this 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 trifluoromethylsulfonic acid. The amount of the acid used is usually within a range of 1.0 to 10 moles per mole of the compound represented by the general formula (11).

[0057] The inert solvent used in this reaction may be any solvent that does not significantly inhibit the progress of this reaction. For example, inert solvents such as chain or cyclic saturated hydrocarbons such as pentane, hexane, cyclohexane, etc., aromatic hydrocarbons such as benzene, toluene, xylene, etc., halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, etc., halogenated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene, etc., chain or cyclic ethers such as diethyl ether, methyl tertiary butyl ether, dioxane, tetrahydrofuran, etc., nitriles such as acetonitrile, propionitrile, etc., esters such as methyl acetate, ketones such as acetone, methyl ethyl ketone, aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone, etc., alcohols such as methanol, ethanol, propanol, butanol, 2-propanol, etc., can be exemplified, and these inert solvents can be used alone or in combination of two or more. The amount used may be appropriately selected usually within the range of 0.1 to 100 L per mole of the compound represented by the general formula (11).

[0058] Since this reaction is an equimolar reaction, each compound may be used in equimolar amounts, but any compound may be used in excess. The reaction temperature in this reaction is usually within the range of about 0°C to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but may usually be appropriately selected within the range of several minutes to 48 hours. After the reaction is completed, the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purifying it by recrystallization, column chromatography, etc. as necessary.

[0059] Manufacturing method of step [b] 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.

[0060] Examples of the base used in this 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 of the base used is usually within a range of 1 to 10 times the molar amount of the compound represented by general formula (9).

[0061] The inert solvent used in this reaction may be any solvent that does not significantly inhibit the progress of this reaction, and examples thereof include inert 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 tertiary butyl ether, dioxane, and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, and 1,3-dimethyl-2-imidazolidinone, and these inert solvents may be used alone or in combination of two or more. The amount of the solvent used may be appropriately selected from the range of usually 0.1 to 100 L per mole of the compound represented by the general formula (9).

[0062] Since this reaction is an equimolar reaction, each compound may be used in equimolar amounts, but any compound may be used in excess. The reaction temperature in this reaction is usually within the range of about 0°C to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but may usually be appropriately selected within the range of several minutes to 48 hours. After the reaction is completed, the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purifying it by recrystallization, column chromatography, etc. as necessary.

[0063] Manufacturing method of step [c] 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.

[0064] The inert solvent used in this reaction may be any solvent that does not significantly inhibit the progress of this reaction. For example, pentane, hexane, cyclohexane, and other linear or cyclic saturated hydrocarbons, benzene, toluene, xylene, and other aromatic hydrocarbons, methylene chloride, chloroform, carbon tetrachloride, and other halogenated hydrocarbons, chlorobenzene, dichlorobenzene, and other halogenated aromatic hydrocarbons, diethyl ether, methyl tertiary butyl ether, dioxane, tetrahydrofuran, and 2-methyltetrahydrofuran, and other linear or cyclic ethers, acetonitrile, propionitrile, and other nitriles, methyl acetate, and other esters, acetone, methyl ethyl ketone, and other ketones, N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, and 1,3-dimethyl-2-imidazolidinone, and other aprotic polar solvents, methanol, ethanol, propanol, butanol, and 2-propanol, and other alcohols, water, and the like can be exemplified. These inert solvents can be used alone or in combination of two or more. The amount used may be appropriately selected usually within the range of 0.1 to 100 L per mole of the compound represented by the general formula (7).

[0065] The reaction temperature in this reaction may be generally in the range of about 0° C. to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but may be appropriately selected generally within the range of several minutes to 48 hours. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purifying it by recrystallization, column chromatography, etc., as necessary.

[0066] Manufacturing method of step [d] The compound represented by the general formula (4) can be produced by condensing the compound represented by the general formula (6) with the malonic acid monoethyl ester represented by the formula (5) by an amidation method commonly used in organic synthesis.

[0067] Manufacturing method of step [e] A compound represented by general formula (3) can be produced by subjecting a compound represented by general formula (4) to a cyclization reaction in the presence of a base and an inert solvent.

[0068] Examples of the base used in this 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 hydrogen carbonate, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate, 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 of the base used is usually within a range of 1 to 10 times the molar amount of the compound represented by general formula (4).

[0069] The inert solvent used in this reaction may be any solvent that does not significantly inhibit the progress of this reaction, and examples thereof include inert 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 tertiary butyl ether, dioxane, and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, 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 of the solvent used may be appropriately selected from the range of usually 0.1 to 100 L per mole of the compound represented by the general formula (4).

[0070] The reaction temperature in this reaction may be generally in the range of about 0° C. to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but may be appropriately selected generally within the range of several minutes to 48 hours. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purifying it by recrystallization, column chromatography, etc., as necessary.

[0071] Manufacturing method of step [f] The compound represented by general formula (1a) of the present invention can be produced by reacting the compound represented by general formula (3) with the compound represented by general formula (2) in the presence of an inert solvent.

[0072] The inert solvent used in this reaction may be any solvent that does not significantly inhibit the progress of this reaction. For example, inert solvents such as chain or cyclic saturated hydrocarbons such as pentane, hexane, cyclohexane, etc., aromatic hydrocarbons such as benzene, toluene, xylene, etc., halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, etc., halogenated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene, etc., chain or cyclic ethers such as diethyl ether, methyl tertiary butyl ether, dioxane, tetrahydrofuran, etc., nitriles such as acetonitrile, propionitrile, etc., esters such as methyl acetate, ketones such as acetone, methyl ethyl ketone, aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone, etc., alcohols such as methanol, ethanol, propanol, butanol, 2-propanol, etc., can be exemplified, and these inert solvents can be used alone or in combination of two or more. The amount used may be appropriately selected usually within the range of 0.1 to 100 L per mole of the compound represented by the general formula (3).

[0073] Since this reaction is an equimolar reaction, each compound may be used in equimolar amounts, but any compound may be used in excess. The reaction temperature in this reaction is usually within the range of about 0°C to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but may usually be appropriately selected within the range of several minutes to 48 hours. After the reaction is completed, the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purifying it by recrystallization, column chromatography, etc. as necessary.

[0074] Manufacturing method 2 [ka]

[0075] {where, R 2 , and R 4 is the same as above. 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) by the following steps [g] and [h].

[0076] Process [g] A process for producing a compound represented by general formula (13) by decarboxylation of a compound represented by general formula (3). Process [h] A process for producing a compound represented by general formula (1b-1) of the present invention by reacting a compound represented by general formula (13) with a compound represented by general formula (12).

[0077] Manufacturing method of step [g] A compound represented by general formula (13) can be produced by reacting a compound represented by general formula (3) in the presence of an inert solvent under heating conditions.

[0078] The inert solvent used in this reaction may be any solvent that does not significantly inhibit the progress of this reaction, and examples thereof include inert 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 tertiary butyl ether, dioxane, and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, and 1,3-dimethyl-2-imidazolidinone, alcohols such as methanol, ethanol, propanol, butanol, and 2-propanol, and water, and these inert solvents may be used alone or in combination of two or more. The amount of the solvent used may be appropriately selected from the range of usually 0.1 to 100 L per mole of the compound represented by the general formula (13).

[0079] The reaction temperature in this reaction may be generally in the range of about 0° C. to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but may be appropriately selected generally within the range of several minutes to 48 hours. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purifying it by recrystallization, column chromatography, etc., as necessary.

[0080] Manufacturing method of step [h] The compound represented by general formula (1b-1) of the present invention can be produced by reacting the compound represented by general formula (13) with the compound represented by general formula (12) in the presence of a base and an inert solvent.

[0081] Examples of bases that can be used in this 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 hydrogen carbonate, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate, 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 of base used is usually within a range of 1 to 10 times the molar amount of the compound represented by general formula (13).

[0082] The inert solvent used in this reaction may be any solvent that does not significantly inhibit the progress of this reaction, and examples thereof include inert 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 tertiary butyl ether, dioxane, and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, 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 of the solvent used may be appropriately selected from the range of 0.1 to 100 L per mole of the compound represented by the general formula (13).

[0083] Since this reaction is an equimolar reaction, each compound may be used in equimolar amounts, but any compound may be used in excess. The reaction temperature in this reaction is usually within the range of about 0°C to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but may usually be appropriately selected within the range of several minutes to 48 hours. After the reaction is completed, the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purifying it by recrystallization, column chromatography, etc. as necessary.

[0084] Manufacturing method 3 [ka]

[0085] {where, R 2 , R 3 and R 4 is the same as above. 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) by the following step [i].

[0086] Process [i] A process for producing a compound represented by general formula (1b-2) by reacting a compound represented by general formula (1a) with a sulfurizing agent.

[0087] Examples of the sulfurizing agent that can be used in this reaction include Lawesson's Reagent and diphosphorus pentasulfide, and the amount of the agent used is usually within a range of 1.0 to 10 times the molar amount of the compound represented by general formula (1a).

[0088] This reaction may or may not use a solvent, but the solvent that can be used in this reaction may be any solvent that does not significantly inhibit the progress of this reaction, and examples of such solvents include inert solvents such as chain or cyclic saturated hydrocarbons such as pentane, hexane, cyclohexane, etc., aromatic hydrocarbons such as benzene, toluene, xylene, etc., halogenated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene, etc., chain or cyclic ethers such as diethyl ether, methyl tertiary butyl ether, dioxane, tetrahydrofuran, etc., nitriles such as acetonitrile, propionitrile, etc., aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, 1,3-dimethyl-2-imidazolidinone, etc., alcohols such as methanol, ethanol, propanol, butanol, 2-propanol, etc., and these inert solvents can be used alone or in combination of two or more. The amount of the solvent used may be appropriately selected from the range of usually 0.1 to 100 L per mole of the compound represented by the general formula (1a).

[0089] The reaction temperature in this reaction may be generally in the range of about 0° C. to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but may be appropriately selected generally within the range of several minutes to 48 hours. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purifying it by recrystallization, column chromatography, etc., as necessary.

[0090] The salts of the compounds represented by general formula (1a), (1b-1), or (1b-2) of the present invention can be produced by reacting the compounds represented by general formula (1a), (1b-1), or (1b-2) with an inorganic or organic base in the presence of an inert solvent.

[0091] Examples of the inorganic or organic base used in the above 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 hydrogen carbonate, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate, 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, and the like. The amount of the base used is usually within a range of 1 to 10 times the molar amount of the compound represented by general formula (1a), (1b-1), or (1b-2).

[0092] The inert solvent used in the above reaction may be any solvent that does not significantly inhibit the progress of the reaction, and examples thereof include inert solvents such as chain or cyclic saturated hydrocarbons such as pentane, hexane, cyclohexane, etc., aromatic hydrocarbons such as benzene, toluene, xylene, etc., halogenated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene, etc., chain or cyclic ethers such as diethyl ether, methyl tertiary butyl ether, dioxane, tetrahydrofuran, etc., nitriles such as acetonitrile, propionitrile, etc., aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, 1,3-dimethyl-2-imidazolidinone, etc., alcohols such as methanol, ethanol, propanol, butanol, 2-propanol, etc., and these inert solvents may be used alone or in combination of two or more. The amount of the solvent used may be appropriately selected from the range of usually 0.1 to 100 L per mole of the compound represented by general formula (1a), (1b-1), or (1b-2).

[0093] The reaction temperature in the above reaction may usually be in the range of about 0° C. to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but may usually be appropriately selected in the range of several minutes to 48 hours. After the reaction is completed, the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purifying it by recrystallization, column chromatography, etc. as necessary.

[0094] Method for producing intermediates 1 [ka]

[0095] {where, R 2 is the same as above. The intermediate for producing the compound of the present invention represented by the general formula (11) can be produced from the compound represented by the general formula (14).

[0096] Manufacturing method The compound represented by the general formula (14) can be reacted with sodium nitrite in concentrated hydrochloric acid, and then reduced with a reducing agent to produce the compound represented by the general formula (11).

[0097] Examples of the reducing agent used in this reaction include sodium sulfite and tin chloride, and the amount of the reducing agent used may be appropriately selected from the range of usually 1.0 to 10 times the molar amount of the compound represented by the general formula (14).

[0098] The reaction temperature in this reaction may be generally in the range of about 0° C. to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but may be appropriately selected generally within the range of several minutes to 48 hours. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purifying it by recrystallization, column chromatography, etc., as necessary.

[0099] Intermediate manufacturing method 2 [ka]

[0100] {where, R 2 is the same as above, and L represents a leaving group such as a halogen atom, a mesyl group, a tosyl group, or a trifluorosulfonyl group.} The intermediate for producing the compound of the present invention represented by the general formula (11) can also be produced from the compound represented by the general formula (15) by the following method.

[0101] Manufacturing method 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.

[0102] The inert solvent used in this reaction may be any solvent that does not significantly inhibit the progress of this reaction, and may be, for example, inert solvents such as chain or cyclic saturated hydrocarbons such as pentane, hexane, cyclohexane, etc., aromatic hydrocarbons such as benzene, toluene, xylene, etc., halogenated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene, etc., chain or cyclic ethers such as diethyl ether, methyl tertiary butyl ether, dioxane, tetrahydrofuran, etc., alcohols such as methanol, ethanol, propanol, butanol, 2-propanol, etc. These inert solvents may be used alone or in combination of two or more. The amount of the solvent used may be appropriately selected from the range of 0.1 to 100 L per mole of the compound represented by the general formula (15).

[0103] Since this reaction is an equimolar reaction, each compound may be used in equimolar amounts, but any compound may be used in excess. The reaction temperature in this reaction is usually within the range of about 0°C to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but may usually be appropriately selected within the range of several minutes to 48 hours. After the reaction is completed, the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purifying it by recrystallization, column chromatography, etc. as necessary.

[0104] Representative examples of the compound represented by general formula (1) of the present invention are shown in Tables 1 and 2 below, but the present invention is not limited to these. In the table, "Me" stands for methyl group, "Et" stands for ethyl group, "n-Pr" stands for normal propyl group, "i-Pr" stands for isopropyl group, "n-Bu" stands for normal butyl group, "t-Bu" stands for tertiary butyl group, "n-Pen" stands for normal pentyl group, "c-Pen" stands for cyclopentyl group, "Ph" stands for phenyl group, and "Bn" stands for benzyl group. The circles in the structural formulas indicate the bond positions. Physical properties are melting point (℃) or H 1 -NMR is shown. 1 -NMR data is shown in Table 6.

[0105] [ka]

[0106] [Table 1]

[0107] [Table 2]

[0108] [Table 3]

[0109]

Table 4

[0110]

Table 5

[0111]

Table 6

[0112]

Table 7

[0113]

Table 8

[0114]

Table 9

[0115]

Table 10

[0116]

Table 11

[0117]

Table 12

[0118]

Table 13

[0119]

Table 14

[0120]

Table 15

[0121]

Table 16

[0122]

Table 17

[0123]

Table 18

[0124]

Table 19

[0125]

Table 20

[0126]

Table 21

[0127]

Table 22

[0128]

Table 23

[0129]

Table 24

[0130]

Table 25

[0131]

Table 26

[0132]

change

[0133]

Table 27

[0134]

Table 28

[0135]

Table 29

[0136]

change

[0137]

Table 30

[0138]

change

[0139]

Table 31

[0140]

Table 32

[0141]

Table 33

[0142]

change

[0143]

Table 34

[0144]

Table 35

[0145]

Table 36

[0146]

Table 37

[0147]

Table 38

[0148]

Table 39

[0149]

Table 40

[0150]

Table 41

[0151] [Table 42]

[0152] [Table 43]

[0153] The agricultural and horticultural insecticide containing the compound represented by the general formula (1) of the present invention or a salt thereof as an active ingredient is suitable for controlling various agricultural, forestry, horticultural and grain storage pests, sanitary pests, nematodes and other pests that damage rice, fruit trees, vegetables, other crops and ornamental plants.

[0154] Examples of the above-mentioned pests or nematodes include the following. Lepidoptera (Lepidoptera) pests include, for example, Parasa consocia, Anomis mesogona, Papilio xuthus, Matsumuraeses azukivora, Ostrinia scapulalis, Spodoptera exempta, Hyphantria cunea, Ostrinia furnacalis, Pseudaletia separata, Tinea translucens, Bactra furfuryla, Parnara guttata, 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, Archipelago tortrix xylosteanus, Agrotis segetum, Tetramoera schistaceana, Papilio machaon hippocrates, Endoclyta sinensis, Lyonetia prunifoliella, Phyllonorycterringoneella, chestnut moth (Cydia kurokoi), chestnut green moth (Eucoenogenes aestuosa), grapeberry moss (Lobesia botrana), black-spotted green moth (Latoia sinica), black-spotted moth (Euzophera batangensis), mulberry moth (Phalonidia mesotypa), mulberry spotted moth (Spilosoma imparilis), mulberry moth (Glyphodes pyloalis), mulberry moth (Olethreutes mori), brown moth (Tineola bisselliella), bat moth (Endoclyta excrescens), Japanese rice moth (Nemapogon granellus), small grass moth (Synanthedon hector), codling moth (Cydia pomonella), diamondback moth (Plutella xylostella, rice leaf borer (Cnaphalocrocis medinalis), southern pink borer (Sesamia calamistis), rice leaf borer (Scirpophaga incertulas), grass moth (Pediasia teterrellus), potato tuber moth (Phthorimaea operculella), oriental horn moth (Stauropus fagi persimilis), beetle moth (Etiella zinckenella), beet armyworm (Spodoptera exigua), beetle bark moth (Palpifer sexnotata), beetle armyworm (Spodoptera mauritia), rice leaf borer (Scirpophaga innotata), beetle cutworm (Xestia c-nigrum), beetle cutworm (Spodoptera depravata, Ephestia kuehniella, Angerona prunaria, Clostera anastomosis, Pseudoplusia includens, Matsumuraeses falcana, Helicoverpaassulta, Autographa nigrisigna, Agrotis ipsilon, Euproctis pseudoconspersa, Adoxophyes orana, Caloptilia theivora, Homona magnanima, Ephestia elutella, Eumeta minuscula, Clostera anachoreta, Heliothis maritima, Sparaganothis pilleriana, Busseola fusca, Euproctis subflava, Biston robustum, Heliothis zea, Aedia leucomelas, Japanese pear moth (Narosoideus flavidorsalis), Japanese pear moth (Viminia rumicis), Japanese pear short moth (Bucculatrix pyrivorella), Japanese pear fruit moth (Grapholita molesta), Japanese pear leaf moth (Spulerina astaurota), Japanese pear meal moth (Ectomyelois pyrivorella), Japanese chilo borer moth (Chilo suppressalis), Japanese onion leaf moth (Acrolepiopsis sapporensis), Japanese meal moth (Plodia interpunctella), Japanese yellow meal moth (Hellula undalis), Japanese white moth (Sitotroga cerealella), Japanese cutworm moth (Spodoptera litura), Japanese tortrix moth (Eucosma aporema), Japanese rose moth (Acleris comariana), Japanese black moth (Scopelodes contractus), Orgyia thyellina, Spodoptera frugiperda, Ostrinia zaguliaevi, Narangaaenescens, Andraca bipunctata, Paranthrene regalis, Acosmeryx castanea, Phyllocnistis toparcha, Endopiza viteana, Eupoecillia ambiguella, Anticarsia gemmatalis, Cnephasia cinereipalpana, Lymantria dispar, Dendrolimus spectabilis, Leguminivore moth, Maruca testulalis, Matsumuraeses phaseoli, Caloptilia soyella, citrus leafminer (Phyllocnistis citrella), white-spotted leafminer (Omiodes indicate), brown tortrix moth (Archips fuscocupreanus), three-leaved golden moth (Acanthoplusia agnata), bagworm moth (Bambalina sp.), peach fruit moth (Carposina niponensis), peach spotted moth (Conogethes punctiferalis), peach moths (Synanthedon sp.), peach leafminer (Lyonetia clerkella), common white butterfly (Papilio helenus), common yellow butterfly (Colias erate poliographus), common black orca (Phalera flavescens), cabbage white butterfly (Pieris rapae crucivora), cabbage white butterfly (Pieris rapae), Euproctis similis, Acrolepiopsis suzukiella, Ostrinia nubilalis, Mamestra brassicae, Ascotis graminearum,selenaria, Phtheochroides clandestina, Hoshinoa adumbratana, Odonestis pruni japonensis, Triaena intermedia, Adoxophyes orana fasciata, Grapholita inopinata, Spironota ocellana, Spironota lechriaspis, Illiberis pruni, Argyresthia conjugella, Caloptilia zachrysa, Archips breviplicanus, Anomis flava, Pectinophora gossypiella, Notarcha derogata, Diaphania indica, Heliothis virescens, and Earias cupreoviridis.

[0155] Hemiptera (Hemiptera) pests include, for example, Nezara antennata, Stenotus rubrovittatus, Graphosoma rubrolineatum, Trigonotylus coelestialium, Aeschynteles maculatus, Creontiades pallidifer, Dysdercus cingulatus, Chrysomphalus ficus, Aonidiella aurantii, Graptopsaltria nigrofuscata, American long-horned stink bug (Blissusleucopterus), Icerya scale bug (Icerya purchasi), striped stink bug (Piezodorus hybneri), rice stink bug (Lagynotomus elongatus), rice leafhopper (Thaia subrufa), rice black stink bug (Scotinophara lurida), thorny long-horned aphid (Sitobion ibarae), Iwasaki stink bug (Stariodes iwasakii), pale scale insect (Aspidiotus destructor), pale-leaved rice bug (Taylorilygus pallidulus), plum horn aphid (Myzusmumecola), plum white scale insect (Pseudaulacaspis prunicola), pea aphid (Acyrthosiphon pisum), spider bug (Anacanthocoris striicornis), black-spotted stink bug (Ectometopterus micantulus), large spurred spotted bug (Eysarcoris lewisi), large stink bug (Molipteryx fuliginosa), leafhopper (Cicadella viridis), red-veined aphid (Rhopalosophumrufiabdominalis, olive scale (Saissetia oleate), greenhouse whitefly (Trialeurodes vaporariorum), oak leafhopper (Aguriahana quercus), mirid bugs (Lygus spp.), Japanese whitefly (Euceraphis punctipennis), citrus scale (Andaspis kashicola), citrus scale (Coccus pseudomagnoliarum), citrus long-winged bug (Cavelerius saccharivorus), chrysanthemum long-horned bug (Galeatus spinifrons), chrysanthemum long-horned aphid (Macrosiphoniella sanborni), yellow scale (Aonidiella citrina), brown marmorated stink bug (Halyomorpha mista), Japanese burrowing bug (Stephanitis fasciicarina), Japanese burrowing psylla (Trioza camphorae), spider bug (Leptocorisa chinensis), chestnut psylla (Trioza quercicola), walnut burrowing bug (Uhlerites latius), grape leaf hopper (Erythroneura comes), black-legged stink bug (Paromius exiguus), black scale insect (Duplaspidiotus claviger), black leafhopper (Nephotettix nigropictus), black-legged mosquito (Halticiellus insularis), black planthopper (Perkinsiella saccharicida), black apple psylla (Psylla malivorella), mulberry psylla (Anomomeura mori), Mulberry mealybug (Pseudococcus longispinis), Mulberry white scale bug (Pseudaulacaspis pentagona), Mulberry cotton scale bug (Pulvinaria kuwacola), Green grass bug (Apolygus lucorum), Japanese long-legged stink bug (Togohemipterus, Toxoptera aurantii, Saccharicoccus sacchari, Geoica lucifuga, Numata muiri, Comstockaspis perniciosa, Unaspis citri, Aulacorthum solani, Eysarcoris ventralis, Bemisia argentifolii, Cicadella spectra, Aspidiotus hederae, Liorhyssus hyalinus, Calophya nigridorsalis, Sogatella furcifera, Megoura crassicauda, ​​Brevicoryne brassicae, Aphis glycines, Leptocorisa oratorius, Nephotettix virescens, Uroeucon formosanum, Cyrtopeltis tennuis, Bemisia tabaci, Lecanium persicae, Parlatoria theae, Pseudaonidia paeoniae), Tea green leafhopper (Empoasca onukii), German stink bug (Plautia stali), Tulip root aphid (Dysaphis tulipae), Tulip long-horn aphid (Macrosiphum euphorbiae), Azalea leafhopper (Stephanitis pyrioides), Ceroplastesceriferus, Camellia black spotted scale (Parlatoria camelliae), Green rice bug (Apolygus spinolai), Green rice leafhopper (Nephotettix cincticeps), Shiny green stink bug (Glaucias subpunctatus), Sugar beet stink bug (Orthotylus flavosparsus), Corn aphid (Rhopalosiphum maidis), Corn planthopper (Peregrinus maidis), Spiny spotted bug (Eysarcoris parvus), Bedbug (Cimex lectularius), Japanese chestnut psylla (Psylla abieti), Brown planthopper (Nilaparvata lugens), Pittosporum psylla (Psylla tobirae), Long-legged bug (Eurydema rugosum), Pear aphid (Schizaphis piricola, Pear psylla (Psylla pyricola), Pear spotted scale (Parlatoreopsis pyri), Pear earworm (Stephanitis nashi), Pear mealybug (Dysmicoccus wistariae), Pear long scale (Lepholeucaspis japonica), Pear aphid (Sappaphis piri), False radish aphid (Lipaphis erysimi), Onion aphid (Neotoxoptera formosana), Husk beetle aphid (Rhopalosophum nymphaeae), Rose leafhopper (Edwardsianarosae), Japanese long scale (Pinnaspisaspidistrae), Alder psylla (Psylla alni), Alder long scale (Speusotettix subfusculus, alder leafhopper (Alnetoidia alneti), barnyard planthopper (Sogatella panicicola), long-horned rice bug (Adelphocoris lineolatus), small red spotted stink bug (Dysdercus poecilus), small black scale (Parlatoria ziziphi), small grasshopper (Uhleritesdebile, Laodelphax striatellus, Eurydema pulchrum, Cletus trigonus, Clovia punctata, Empoasca sp., Coccus hesperidum, Pachybrachius luridus, Planococcus kraunhiae, Stenotus binotatus, Arboridia apicalis, Macrosteles fascifrons, Dolycoris baccarum, Adelphocoris adelphoris triannulatus, grape root aphid (Viteus vitifolii), ground cherry bug (Acanthocoris sordidus), narrow-legged stink bug (Leptocorisa acuta), narrow-winged long-legged bug (Macropes obnubilus), narrow-legged stink bug (Cletus punctiger), narrow-legged stink bug (Riptortus clavatus), potato piscillides (Paratrioza cockerelli), Japanese bush cricket (Aphrophora costalis), Japanese grass cricket (Lygus disponsi), Japanese spotted grass cricket (Lygus saundersi), pine mealybug (Crisicoccus pini), pine leafhopper (Empoasca abietis), Matsumoto mealybug (Crisicoccus matsumotoi), bean aphid (Aphis craccivora), round stink bug (Megacopta punctatissimum), white spotted stink bug (Eysarcoris guttiger), citrus scale (Lepidosaphes beckii), citrus psyllid (Diaphorina citri), citrus black aphid (Toxoptera citricidus), citrus mealybug (Planococcuscitri), citrus whitefly (Dialeurodes citri), citrus spiny whitefly (Aleurocanthus spiniferus), citrus mealybug (Pseudococcus citriculus), citrus leafhopper (Zyginella citri), citrus cotton scale (Pulvinaria citricola), citrus flathead scale (Coccus discrepans), citrus round scale (Pseudaonidia duplex), citrus cotton scale (Pulvinaria aurantii), dogwood scale (Lecanium corni), southern green stink bug (Nezara viridula), wheat grass worm (Stenodema calcaratum), wheat curl aphid (Rhopalosiphum padi), wheat long-horn aphid (Sitobion akebiae), wheat green aphid (Schizaphis graminum), wheat leafhopper (Sorhoanus tritici), wheat straw aphid (Brachycaudus helichrysi), purple stink bug (Carpocoris purpureipennis), peach aphid (Myzus persicae), peach butterbur aphid (Hyalopterus pruni), willow aphid (Aphis farinose yanagicola), willow powderhopper (Metasalis populi), Yanon scale (Unaspis yanonensis), mountain asahi psylla (Mesohomotoma camphorae), snow willow aphid (Aphis spiraecola), apple aphid (Aphis pomi), apple persimmon scale (Lepidosaphes ulmi), Apple psylla (Psylla mali), Apple black grass bug (Heterocordylus flavipes), Apple leaf aphid (Myzus malisuctus), Apple leaf aphid (Aphidonuguis mali), Apple leafhopper (Orientus ishidai), Apple bird aphid (Ovatusmalicolens, Eriosoma lanigerum, Ceroplastes rubens, and Aphis gossypii.

[0156] Examples of pests of the order Coleoptera include the Japanese longhorn beetle (Xystrocera globosa), the green leaf beetle (Paederus fuscipes), the green flower beetle (Eucetonia roelofsi), the azuki bean weevil (Callosobruchus chinensis), the sweet potato weevil (Cylas formicarius), the alfalfa weevil (Hypera postica), the rice weevil (Echinocnemus squameus), the rice leaf beetle (Oulema oryzae), the rice leaf beetle (Donacia provosti), the rice water weevil (Lissorhoptrus oryzophilus), the potato leaf beetle (Colasposoma dauricum), the potato weevil (Euscepes postfasciatus), and the common ladybird beetle (Epilachna varivestis), bean weevil (Acanthoscelides obtectus), western corn rootworm (Diabrotica virgifera virgifera), plum vest weevil (Involvulus cupreus), cucumber leaf beetle (Aulacophora femoralis), pea weevil (Bruchus pisorum), large 24-spotted ladybird (Epilachna vigintioctomaculata), oak leaf beetle (Carpophilus dimidiatus), tortoise leaf beetle (Cassida nebulosa), yellow-legged flea beetle (Luperomorpha tunebrosa), striped flea beetle (Phyllotreta striolata), yellow-spotted longhorn beetle (Psacothea hilaris), yellow spotted longhorn beetle (Aeolesthes chrysothrix), chestnut weevil (Curculio sikkimensis), Japanese beetle (Carpophilus hemipterus), flower beetle (Oxycetonia jucunda), corn rootworms (Diabrotica spp.), scarab beetle (Mimela splendens), rice weevil (Sitophilus zeamais), red flour beetle (Tribolium castaneum), rice weevil (Sitophilus oryzae), lesser red flour beetle (Palorus subdepressus), cockle beetle (Melolontha japonica), longhorn beetle (Anoplophora malasiaca), mealworm beetle (Neatus picipes), Colorado potato beetle (Leptinotarsa ​​decemlineata), southern corn rootworm (Diabrotica undecimpunctata howardi), grass-lined weevil (Sphenophorus venatus), yellow spotted long-necked beetle (Crioceris quatuordecimpunctata), plum curculio (Conotrachelus nenuphar, radish weevil (Ceuthorhynchidius albosuturalis), radish leaf beetle (Phaedon brassicae), cigarette beetle (Lasioderma serricorne), small weevil (Sitona japonicus), brown scarab beetle (Adoretus tenuimaculatus), brown mealworm beetle (Tenebrio molitor), brown monkey beetle (Basilepta balyi), nail weevil (Hypera nigrirostris), tench leaf beetle (Chaetocnema concinna), cuprea beetle (Anomala cuprea), long-legged beetle (Heptophylla picea), 24-spotted ladybird beetle (Epilachna vigintioctopunctata), northern corn rootworm (Diabrotica longicornis), flower beetle (Eucetonia pilifera), wireworms (Agriotes spp.), Attagenus unicolor japonicus, Pagria signata, Anomala rufocuprea, Palorus ratzeburgii, Alphitobius laevigatus, Anthrenus verbasci, Lyctus brunneus, Tribolium confusum, Medythia nigrobilineata, Xylotrechus pyrrhoderus, Epitrix cucumeris, Tomicus piniperda, Monochamus alternatus alternatus, Japanese beetle (Popillia japonica), bean tiger beetle (Epicauta gorhami), maize weevil (Sitophilus zeamais), peach vest weevil (Rhynchites heros), vegetable weevil (Listroderes costirostris), cowpea weevil (Callosobruchus maculatus), apple weevil (Phyllobius armatus), apple blossom weevil (Anthonomus pomorum), blue leaf beetle (Linaeidea aenea), and boll weevil (Anthonomus grandis).

[0157] Examples of pests of the Diptera (Flying flies) 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 suzukii, and others. japonica), Muscina stabulans, Megaselia spiracularis and other flea flies, Clogmia albipunctata, Tipula aino, Phormia regina, Culex tritaeniorhynchus, Anopheles sinensis, Hylemya brassicae, Asphondylia sp.), seed fly (Delia platura), onion fly (Delia antiqua), European cherry fruit fly (Rhagoletis cerasi), Culex pipiens molestus Forskal, Mediterranean fruit fly (Ceratitis capitata), Siberian fungus fly (Bradysia agrestis), beet root fly (Pegomya cunicularia), tomato leafminer (Liriomyza sativae), eggplant leafminer (Liriomyza bryoniae), groundminer (Chromatomyia horticola), onion leafminer (Liriomyza chinensis), southern house mosquito (Culex quinquefasciatus), Aedes aegypti, Aedes albopictus albopictus, Liriomyza trifolii, Liriomyza sativae, Dacus dorsalis, Dacus tsuneonis, Sitodiplosis mosellana, Meromuza nigriventris, Anastrea ludens, and Rhagoletis pomonella.

[0158] Examples of Hymenoptera (Hymenoptera) pests include Pristomyrmex pungens, ant wasps, Monomorium pharaohnis, Pheidole noda, Athalia rosae, Dryocosmus kuriphilus, Formica fusca japonica, hornets, Athalia infumata infumata, Arge pagana, Athalia japonica, leaf-cutter ants (Acromyrmex spp.), Solenopsis spp., Arge mali, and Ochetellus glaber.

[0159] Examples of Orthoptera (orthoptera) pests include Homorocoryphus lineosus, Gryllotalpa sp., Oxya hyla intricata, Oxya yezoensis, Locusta migratoria, Oxya japonica, Homorocoryphus jezoensis, and Teleogryllus emma.

[0160] Examples of pests of the order Thripida include Selenothrips rubrocinctus, Stenchaetothrips biformis, Haplothrips aculeatus, Ponticulothrips diospyrosi, Thrips flavus, Anaphothrips obscurus, Liothrips floridensis, Thrips simplex, Thrips nigropilosus, Heliothrips haemorrhoidalis, and 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 alliorum), Thrips hawaiiensis, Haplothrips kurdjumovi, Chirothrips manicatus, Frankliniella intonsa, Thrips coloratus, Franklinella occidentalis, Thrips palmi,palmi), Frankliniella lilivora, and Liothrips vaneeckei.

[0161] Examples of pests of the order Acarina include ticks such as Leptotrombidium akamushi, Tetranychus ludeni, Dermacentor variabilis, Tetranychus truncatus, Ornithonyssus bacoti, Demodex canis, Tetranychus viennensis, Tetranychus kanzawai, and Rhipicephalus sanguineus, as well as mites such as Cheyletus malaccensis, Tyrophagus putrescentiae, Dermatophagoides farinae, and Latrodectus hasseltii, Dermacentor taiwanicus, Acaphylla theavagrans, Polyphagotarsonemus latus, Aculops lycopersici, Ornithonyssus sylvairum, Tetranychus urticae, Eriophyes chibaensis, Sarcoptes scabiei, Haemaphysalis longicornis, Ixodes scapularis, Tyrophagus similis, Cheyletus eruditus, Panonychus citri, Cheyletus moorei), Brown spider mite (Brevipalpus phoenicis), Ear mite (Octodectes cynotis), House dust mite (Dermatophagoides ptrenyssnus), Japanese mites (Haemaphysalis flava), Japanese ticks (Ixodesovatus, Ryukyu citrus rust mite (Phyllocoptruta citri), apple rust mite (Aculus schlechtendali), apple red mite (Panonychus ulmi), lone star tick (Amblyomma americanum), and red mite (Dermanyssus gallinae), Robin's bulb mite (Rhyzoglyphus robini), and a species of bulb mite (Sancassania sp.).

[0162] Examples of termite pests include Reticulitermes miyatakei, Incisitermes minor, Coptotermes formosanus, Hodotermopsis japonica, Reticulitermes sp., Reticulitermes flaviceps amamianus, Glyptotermes kushimensis, Coptotermes guangzhoensis, Neotermes koshunensis, Glyptotermes kodamai, Glyptotermes satsumensis, Cryptotermes domesticus, Odontotermes formosanus, Glyptotermes nakajimai, Pericapritermes nitobei, and Reticulitermes speratus.

[0163] Examples of cockroach pests include the Siberian cockroach (Periplaneta fuliginosa), the German cockroach (Blattella germanica), the Asian cockroach (Blatta orientalis), the Brown cockroach (Periplaneta brunnea), the Lesser German cockroach (Blattella lituricollis), the Japanese cockroach (Periplaneta japonica), and the American cockroach (Periplaneta americana).

[0164] Examples of the order Siphonaptera include the human flea (Pulex irritans), the cat flea (Ctenocephalides felis), and the chicken flea (Ceratophyllus gallinae).

[0165] Examples of nematodes include the strawberry root nematode (Nothotylenchus acris), the rice root nematode (Aphelenchoides besseyi), the northern root nematode (Pratylenchus penetrans), the northern root nematode (Meloidogyne hapla), the sweet potato root nematode (Meloidogyne incognita), the potato cyst nematode (Globodera rostochiensis), the Java root nematode (Meloidogyne javanica), the soybean cyst nematode (Heterodera glycines), the southern root nematode (Pratylenchus coffeae), the rice root nematode (Pratylenchus neglectus), and the citrus root nematode (Tylenchus semipenetrans).

[0166] Examples of mollusks include the apple snail (Pomacea canaliculata), the African snail (Achatina fulica), the slug (Meghimatium bilineatum), the brown slug (Lehmannina valentiana), the red slug (Limax flavus), and the light blue snail (Acusta despecta sieboldiana).

[0167] The agricultural and horticultural insecticide of the present invention also has a strong insecticidal effect against another pest, the tomato horn moth (Tuta absoluta).

[0168] Examples of animal parasitic mites that are targets of control 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, fowl mites such as Dermacentor gallinae, Ornithonyssus sylviarum, and Ornithonyssus bursa, Eutrombicula wichmanni, Leptotrombidium akamushi, Leptotrombidium pallidum, Leptotrombidium fuji, Leptotrombidium tosa, Neotrombicula chiggers such as Eutrombicula alfreddugesi, Helenicula miyagawai, Cheyletiella yasguri, Cheyletiellaparasitivorax, and Cheyletiella blakei; Psoroptes cuniculi, Chorioptes bovis, Otodectes cynotis, Sarcoptes scabiei, and Notoedres cati; and Demodex canis.

[0169] Other fleas to be controlled include, for example, external parasitic wingless insects belonging to the Siphonaptera order, more specifically, fleas belonging to the Pulicidae and Ceratephyllus families. Examples of fleas belonging to the Pulicidae family include Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Echidnophaga gallinacea, Xenopsylla cheopis, Leptopsylla segnis, Nosopsyllus fasciatus, and Monopsyllus anisus.

[0170] Further examples of external parasites to be controlled include lice such as cattle lice (Haematopinus eurysternus), horse lice (Haematopinus asini), sheep lice (Dalmalinia ovis), cow lice (Linognathus vituli), pig lice (Haematopinus suis), pubic lice (Phthirus pubis), and head lice (Pediculus capitis), as well as lice such as dog lice (Trichodectes canis), and blood-sucking dipteran pests such as horse flies (Tabanus trigonus), cow lice (Culicoides schultzei), and nail gnats (Simulium ornatum). Examples of internal parasites include nematodes such as lungworms, trichozoans, tuberculous worms, gastric parasites, roundworms, and filarial worms; tapeworms such as Diphyllobothrix mansoni, Diphyllobothrix latissimus, Tapeworm duodena, Tapeworm multiheadi, Echinococcus granulosus, and Echinococcus multilocularis; trematodes such as Schistosoma japonicum and Fasciola hepatica; and protozoans such as coccidia, malaria parasites, intestinal sarcocystis, Toxoplasma, and Cryptosporidium.

[0171] The agricultural and horticultural insecticide containing the compound represented by the general formula (1) or its salt as an active ingredient of the present invention has a remarkable control effect against the above-mentioned pests that cause damage to paddy field crops, field crops, fruit trees, vegetables, other crops, and flowers, etc., and therefore the expected effect of the agricultural and horticultural insecticide of the present invention can be achieved by treating the seedling facility, paddy field, field, fruit trees, vegetables, other crops, flowers, etc., paddy field water, stems and leaves, soil, etc. of the seeds ...

[0172] Useful plants for which the agricultural and horticultural insecticide of the present invention can be used are not particularly limited, and examples thereof include cereals (e.g., rice, barley, wheat, rye, oats, corn, etc.), beans (soybeans, adzuki 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 vegetables (cabbage, tomato, spinach, broccoli, lettuce, onion, green onion (chives, scallions), green peppers, eggplant, strawberries, peppers, okra, Chinese chives, etc.), root vegetables (carrots, potatoes, sweet potatoes, taro, daikon radishes, turnips, lotus roots, burdock, garlic, radishes, etc.), and the like. Examples of plants that can be used include crops for processing (cotton, hemp, beets, hops, sugar cane, sugar beets, olives, rubber, coffee, tobacco, tea, etc.), melons (pumpkin, cucumber, watermelon, Sakwau-ri, melon, etc.), pasture grasses (orchard grass, sorghum, timothy, clover, alfalfa, etc.), turfgrass (Korean grass, bentgrass, etc.), ornamental crops for flavorings and the like (lavender, rosemary, thyme, parsley, pepper, ginger, etc.), flowers (chrysanthemum, rose, carnation, orchid, tulip, lily, etc.), garden trees (ginkgo, cherry trees, aoki, etc.), and forest trees (abarch firs, spruces, pines, hiba, cedar, cypress, eucalyptus, etc.).

[0173] The above-mentioned "plant" also includes plants to which resistance has been imparted by classical breeding methods or genetic engineering techniques to HPPD inhibitors such as isoxaflutole, ALS inhibitors such as imazethapyr and thifensulfuron-methyl, EPSP synthase inhibitors such as glyphosate, glutamine synthase inhibitors such as glufosinate, acetyl-CoA carboxylase inhibitors such as sethoxydim, and herbicides such as bromoxynil, dicamba and 2,4-D.

[0174] Examples of "plants" that have been given resistance by classical breeding methods include rapeseed, wheat, sunflower, and rice that are resistant to imidazolinone ALS inhibitor herbicides such as imazethapyr, which are already sold under the trade name Clearfield (registered trademark). Similarly, soybeans that have been resistant to sulfonylurea ALS inhibitor herbicides such as thifensulfuron methyl by classical breeding methods are already sold under the trade name STS soybeans. Similarly, examples of plants that have been given resistance to acetyl-CoA carboxylase inhibitors such as trione oxime and aryloxyphenoxypropionic acid herbicides by classical breeding methods include SR corn. Furthermore, plants to which resistance to acetyl-CoA carboxylase inhibitors has been imparted 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), and the like. By introducing such mutant acetyl-CoA carboxylase genes into plants by genetic recombination technology, or by introducing a mutation involved in imparting resistance into plant acetyl-CoA carboxylase, it is possible to produce plants resistant to acetyl-CoA carboxylase inhibitors. Furthermore, by introducing a nucleic acid with a base substitution mutation, as typified by the chimeraplasty technology (Gura T. 1999. Repairing the Genome's Spelling Mistakes. Science 285: 316-318.), into plant cells to introduce a site-specific amino acid substitution mutation into the acetyl-CoA carboxylase gene, ALS gene, or the like of a plant, it is possible to produce plants resistant to acetyl-CoA carboxylase inhibitors, ALS inhibitors, or the like, and the agricultural and horticultural insecticide of the present invention can also be used for such plants.

[0175] Further toxins expressed in transgenic plants include insecticidal proteins from Bacillus cereus and Bacillus popilia; δ-endotoxins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C from Bacillus thuringiensis, insecticidal proteins such as VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins from nematodes; toxins produced by animals such as scorpion toxins, spider toxins, wasp toxins or insect-specific neurotoxins; fungal toxins; plant lectins; agglutinins; trypsin inhibitors, serine protease inhibitors, patatin, cysta These include protease inhibitors such as ricin and papain inhibitors; ribosome-inactivating proteins (RIPs) such as ricin, maize-RIP, abrin, rufin, saporin, and bryodin; steroid metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glucosyltransferase, and 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.

[0176] Toxins expressed in such transgenic plants also include hybrid toxins, partially deleted toxins, and modified toxins of δ-endotoxin proteins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9C, Cry34Ab, or Cry35Ab, or insecticidal proteins such as VIP1, VIP2, VIP3, or VIP3A. Hybrid toxins are produced by new combinations of different domains of these proteins using recombinant technology. As a partially deleted toxin, Cry1Ab, which has a deleted part of its amino acid sequence, is known. As a modified toxin, one or more amino acids of the natural toxin are replaced. Examples of these toxins and recombinant plants capable of synthesizing these toxins are described in EP-A-0 374 753, WO 93 / 07278, WO 95 / 34656, EP-A-0 427 529, EP-A-451 878, WO 03 / 052073, etc.

[0177] The toxins contained in these recombinant plants confer resistance to pests, particularly to Coleoptera, Hemiptera, Diptera, Lepidoptera, and nematodes. The agricultural and horticultural insecticide of the present invention can be used in combination with or systematized with these techniques.

[0178] The agricultural and horticultural insecticide of the present invention may be used as it is, or appropriately diluted or suspended in water, in an amount effective for controlling pests or nematodes on plants where the occurrence of said pests and nematodes is expected, and for example, for pests and nematodes occurring in fruit trees, grains, vegetables, etc., it can be sprayed on the stems and leaves, or it can be used by immersing seeds in the insecticide, seed dressing, seed treatment such as Calper treatment, mixing in the entire soil layer, row application, mixing in bed soil, cell seedling treatment, planting hole treatment, plant base treatment, top dressing, rice box treatment, water surface application, etc., or by application to soil, etc. and absorption through the roots. In addition, it can be used by application to nutrient solution in nutrient solution (hydroponic) cultivation, fumigation, trunk injection, etc. Furthermore, the agricultural and horticultural insecticide of the present invention may be used in an amount effective for controlling pests as it is, or after being appropriately diluted or suspended in water or the like, in a location where the occurrence of the pest is predicted. For example, it may be sprayed against grain storage pests, house pests, sanitary pests, forest pests, etc., and may also be used as a coating on building materials for houses, for smoking, as bait, etc.

[0179] Seed treatment methods include, for example, a method in which seeds are soaked in a liquid or solid formulation, either diluted or undiluted, to allow the agent to penetrate the seeds; a method in which a solid or liquid formulation is mixed with seeds and dusted to adhere to the seed surface; a method in which the formulation is mixed with an adhesive carrier such as a resin or polymer and then coated on the seeds; and a method in which the formulation is sprayed around the seeds at the same time as planting. The "seed" to be subjected to the seed treatment means a plant body in the early stage of cultivation used for plant propagation, and examples thereof include seeds, as well as bulbs, tubers, seed potatoes, sprouts, corms, bulbs, or plant bodies for vegetative propagation for cultivation by cuttings. The "soil" or "cultivation carrier" for a plant when carrying out the method of use of the present invention refers to a support for cultivating crops, particularly a support for growing roots, and the material is not particularly limited as long as it is a material in which plants can grow, and may be so-called soil, seedling mat, water, etc., and specific materials may be, for example, sand, pumice, vermiculite, diatomaceous earth, agar, gel-like substances, polymeric substances, rock wool, glass wool, wood chips, bark, etc.

[0180] Methods for spraying on crop stems and leaves, or on grain storage pests, house pests, sanitary pests, forest pests, and the like include a method in which a liquid formulation such as an emulsifiable concentrate or flowable concentrate, or a solid formulation such as a wettable powder or wettable granules is appropriately diluted with water and sprayed, a method in which a powder is sprayed, or fumigation, etc. Methods for application to soil include, for example, applying a liquid formulation, with or without dilution, to the base of a plant or a seedbed for raising seedlings, etc.; spraying a granule at the base of a plant or a seedbed for raising seedlings, etc.; spraying a dust, wettable powder, water dispersible granule, granule, etc. and mixing it with the entire soil before sowing or transplanting; and spraying a dust, wettable powder, water dispersible granule, granule, etc. in planting holes, rows, etc. before sowing or planting plants.

[0181] For application to rice seedling boxes, the formulation may be in the form of a dust, water dispersible granule, granule, etc., depending on the application time, for example, application at the time of sowing, application during the greening period, application at the time of transplanting, etc. Application can also be by mixing with the culture soil, and the culture soil can be mixed with a dust, water dispersible granule, or granule, for example, by mixing with the bed soil, covering soil, or the entire culture soil. It may also be applied by simply layering the culture soil and various formulations alternately. For application to paddy fields, solid preparations such as jumbo, pack, granule, and granular water dispersible agent, or liquid preparations such as flowable and emulsion are usually sprayed on flooded paddy fields. In addition, at the time of rice planting, appropriate preparations can be sprayed or injected into the soil as they are or mixed with fertilizer. In addition, by using emulsion, flowable, or other liquids at the water inlet of paddy fields such as water inlets and irrigation equipment, application can be labor-saving along with the water supply.

[0182] In field crops, the treatment can be applied to the seeds or to the cultivation carriers adjacent to the plant body during the sowing to seedling raising period. In the case of plants that are directly sown in the field, in addition to direct treatment to the seeds, treatment to the base of the plant during cultivation is preferred. Spraying treatment can be performed using granules, or irrigation treatment can be performed in liquid form with or without dilution in water. Another preferred treatment is to mix the granules with the cultivation carrier before sowing and then sowing. As treatments for cultivated plants to be transplanted during the sowing and seedling raising stage, in addition to direct treatment of seeds, irrigation of liquid agents or spraying of granules on seedling beds is preferred. It is also preferred to apply granules to the planting hole at the time of planting or to mix them into the cultivation carrier near the transplanting site. The agricultural and horticultural insecticide of the present invention is generally formulated into a convenient form for use according to the usual methods for formulating agricultural chemicals. That is, the compound represented by the general formula (1) of the present invention or a salt thereof may be mixed in an appropriate ratio with an appropriate inert carrier, or if necessary, with an auxiliary, and then dissolved, separated, suspended, mixed, impregnated, adsorbed or attached to the compound to be formulated into an appropriate dosage form, such as a suspension, emulsion, liquid, wettable powder, water dispersible granule, granules, powder, tablet, pack, etc., for use.

[0183] The composition of the present invention (agricultural and horticultural insecticide or animal parasite control agent) may contain additives that are commonly used in pesticide formulations or animal parasite control agents, in addition to the active ingredient, as necessary. Examples of the additives include carriers such as solid carriers and liquid carriers, surfactants, dispersants, wetting agents, binders, tackifiers, thickeners, colorants, spreading agents, spreading agents, antifreezing agents, anticaking agents, disintegrants, and antidecomposition agents. If necessary, preservatives, plant pieces, and the like may be used as additives. These additives may be used alone or in combination of two or more.

[0184] Examples of solid carriers include natural minerals such as quartz, clay, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, and diatomaceous earth, inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate, and potassium chloride, organic solid carriers such as synthetic silicic acid, synthetic silicates, starch, cellulose, and plant powders (e.g., sawdust, coconut shells, corn cobs, and tobacco stalks), plastic carriers such as polyethylene, polypropylene, and polyvinylidene chloride, urea, inorganic hollow bodies, plastic hollow bodies, fumed silica (white carbon), etc. These may be used alone or in combination of two or more.

[0185] Examples of liquid carriers include monohydric alcohols such as methanol, ethanol, propanol, isopropanol, and butanol; polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, and glycerin; polyhydric alcohol compounds such as propylene glycol ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, and cyclohexanone; ethers such as ethyl ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether, and THF; normal paraffin; naphthene; Examples of the solvent include aliphatic hydrocarbons such as isoparaffin, kerosene, and mineral oil, aromatic hydrocarbons such as benzene, toluene, xylene, solvent naphtha, and alkylnaphthalene, halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride, esters such as ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate, and dimethyl adipate, lactones such as γ-butyrolactone, amides such as dimethylformamide, diethylformamide, dimethylacetamide, and N-alkylpyrrolidinone, nitriles such as acetonitrile, sulfur compounds such as dimethyl sulfoxide, vegetable oils such as soybean oil, rapeseed oil, cottonseed oil, and castor oil, and water. These may be used alone or in combination of two or more.

[0186] Examples of surfactants used as dispersants or 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 alkylaryl ethers, polyoxyethylene alkylphenyl ethers, polyoxyethylene dialkylphenyl ethers, polyoxyethylene alkylphenyl ether formalin condensates, polyoxyethylene polyoxypropylene block copolymers, polystyrene polyoxyethylene block polymers, alkyl polyoxyethylene polypropylene block copolymer ethers, polyoxyethylene alkylamines, polyoxyethylene fatty acid amides, polyoxyethylene fatty acid bisphenyl ethers, polyalkylene benzyl phenyl ethers, polyoxyalkylene styryl phenyl ethers, acetylenic diols, polyoxyalkylene-added acetylenic diols, polyoxyethylene ether-type silicones, ester-type silicones, fluorine nonionic surfactants such as polyoxyethylene castor oil and polyoxyethylene hydrogenated castor oil; anionic surfactants such as alkyl sulfates, polyoxyethylene alkyl ether sulfates, polyoxyethylene alkyl phenyl ether sulfates, polyoxyethylene styryl phenyl ether sulfates, alkyl benzene sulfonates, alkyl aryl sulfonates, lignin sulfonates, alkyl sulfosuccinates, naphthalene sulfonates, alkyl naphthalene sulfonates, salts of formalin condensates of naphthalene sulfonic acid, salts of formalin condensates of alkyl naphthalene sulfonic acid, fatty acid salts, polycarboxylates, polyacrylates, N-methyl-fatty acid sarcosinates, resin salts, polyoxyethylene alkyl ether phosphates, and polyoxyethylene alkyl phenyl ether phosphates; cationic surfactants such as alkyl amine salts such as laurylamine hydrochloride, stearylamine hydrochloride, oleylamine hydrochloride, stearylamine acetate, stearylaminopropylamine acetate, alkyl trimethylammonium chloride, and alkyl dimethyl benzalkonium chloride;Amphoteric surfactants such as amino acid type or betaine type surfactants can be used alone or in combination of two or more types.

[0187] Examples of binders and tackifiers include carboxymethylcellulose and its salts, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinylpyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, polyethylene glycol having an average molecular weight of 6,000 to 20,000, polyethylene oxide having an average molecular weight of 100,000 to 5,000,000, phospholipids (e.g., cephalin, lecithin, etc.), cellulose powder, dextrin, modified starch, polyaminocarboxylic acid chelate compounds, crosslinked polyvinylpyrrolidone, copolymers of maleic acid and styrenes, (meth)acrylic acid copolymers, half esters of polymers composed of polyhydric alcohols and dicarboxylic acid anhydrides, water-soluble salts of polystyrene sulfonic acid, paraffin, terpene, polyamide resins, polyacrylates, polyoxyethylene, wax, polyvinyl alkyl ethers, alkylphenol-formalin condensates, and synthetic resin emulsions.

[0188] Examples of thickeners include water-soluble polymers such as xanthan gum, guar gum, diutan gum, carboxymethylcellulose, polyvinylpyrrolidone, carboxyvinyl polymers, acrylic polymers, starch compounds, and polysaccharides, and inorganic fine powders such as high-purity bentonite and fumed silica (white carbon).

[0189] Examples of colorants 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.

[0190] Examples of the antifreeze agent include polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, and glycerin.

[0191] Examples of adjuvants for preventing caking or promoting disintegration include polysaccharides such as starch, alginic acid, mannose, and galactose, polyvinylpyrrolidone, fumed silica (white carbon), ester gum, petroleum resin, sodium tripolyphosphate, sodium hexametaphosphate, metal stearates, cellulose powder, dextrin, methacrylic acid ester copolymers, polyvinylpyrrolidone, polyaminocarboxylic acid chelate compounds, sulfonated styrene-isobutylene-maleic anhydride copolymers, and starch-polyacrylonitrile graft copolymers.

[0192] Examples of the decomposition inhibitor include drying agents such as zeolite, quicklime, and magnesium oxide; antioxidants such as phenol compounds, amine compounds, sulfur compounds, and phosphoric acid compounds; and ultraviolet absorbers such as salicylic acid compounds and benzophenone compounds.

[0193] Examples of preservatives include potassium sorbate and 1,2-benzothiazolin-3-one. Furthermore, other auxiliary agents such as functional spreading agents, activity enhancers such as metabolic decomposition inhibitors such as piperonyl butoxide, antifreeze agents such as propylene glycol, antioxidants such as BHT, and ultraviolet absorbers may also be used as necessary.

[0194] The blending ratio of the active ingredient compound can be adjusted as necessary, and may be appropriately selected from the range of 0.01 to 90 parts by weight in 100 parts by weight of the agricultural and horticultural insecticide of the present invention. For example, in the case of a dust, granule, emulsifiable concentrate or wettable powder, 0.01 to 50 parts by weight (0.01 to 50% by weight based on the total weight of the agricultural and horticultural insecticide) is appropriate.

[0195] The amount of the agricultural and horticultural insecticide of the present invention to be used varies depending on various factors, such as the purpose, target pest, crop growth condition, pest occurrence tendency, weather, environmental conditions, formulation type, application method, application location, application time, etc., but may be appropriately selected depending on the purpose from the range of 0.001 g to 10 kg, preferably 0.01 g to 1 kg, of the active ingredient compound per 10 ares. The agricultural and horticultural insecticide of the present invention can be used in combination with other agricultural and horticultural insecticides, miticides, nematicides, fungicides, biological pesticides, etc. in order to expand the range of pests to be controlled and the optimal control period, or for the purpose of reducing the amount of application. It can also be used in combination with herbicides, plant growth regulators, fertilizers, etc. depending on the application scene.

[0196] Other agricultural and horticultural insecticides, acaricides, and nematocides used for such purposes include, for example, 3,5-xylyl methylcarbamate (XMC), fenobucarb (BPMC), Bt toxin-based insecticides, CPCBS (chlorfenson), DCIP (dichlorodiisopropyl ether), DD (1,3-dichloropropene), DDT, NAC, O-4-dimethylsulfamoylphenyl O,O-diethyl phosphorothioate (DSP), O-ethyl O-4-nitrophenyl phenylphosphonothioate (EPN), tripropylisocyanurate (TPIC), acrinathrin, azadirachtin, and acinonapyr. , azinphos-methyl, acequinocyl, acetamiprid, acetoprole, acephate, abamectin, afidopyropen, avermectin-B, amidoflumet, amitraz, alanycarb, aldicarb ), aldoxycarb, aldrin, alpha-endosulfan, alpha-cypermethrin, albendazole, allethrin, isazofos, isamidofos, isoamidofos, isoxathion, isocycloseram, isofenphos, isoprocarb (MIPC), epsilon-metofluthrin,Epsilon-momfluorothrin, ivermectin, imicyafos, imidacloprid, imiprothrin, indoxacarb, esfenvalerate, ethiofencarb, ethion, ethiprole, etoxazole, etofenprox, ethoprophos, etrimfos, emamectin, emamectin-benzoate, endosulfan, empenthrin, oxazosulfyl , oxamyl, oxydemeton-methyl, oxydeprofos (ESP), oxibendazole, oxfendazole, potassium oleate, sodium oleate oleate, cadusafos, kappa-bifenthrin, cartap, carbaryl, carbosulfan, carbofuran, gamma-cyhalothrin, xylylcarb, quinalphos, kinoprene, chinomethionate, cloethocarb, clothianidin, clofentezine, chromafenozide, chlorantraniliprole, chlorethoxyfos, chlordimeform,Chlordane, chlorpyrifos, chlorpyrifos-methyl, chlorphenapyr, chlorfenson, chlorfenvinphos, chlorfluazuron, chlorobenzilate, chlorobenzoate, chloroprallethrin, dicofol, salithion, cyhalodiamide, cyanophos: CYAP, diafenthiuron, diamidafos, cyantraniliprole, theta-cypermethrin, dienochlor, cyetpyrafen, cyenopyrafen, dioxabenzofos, diofenolan, sigma-cypermethrin, cyclaniliprole, dichlophenthion (ECP), cycloprothrin, dichlorvos (dichlorvos: DDVP), dichloromezotiaz, disulfoton, dinotefuran, cyhalodiamide, cyhalothrin, cyphenothrin, cyfluthrin, diflubenzuron, cyflumetofen, diflovidadin, cyproflanilide, cyhexatin, cypermethrin, dimethylvinphos,Dimethoate, dimpropyridaz, dimefluthrin, silafluofen, cyromazine, spidoxamat, spinetoram, spinosad, spirodiclofen, spirotetramat, spiropidione, spiromesifen, sulfluramid, sulpropion Sulprofos, sulfoxaflor, zeta-cypermethrin, diazinon, tau-fluvalinate, dazomet, thiacloprid, thiamethoxam, tioxazafen, thiodicarb, thiocyclam, thiosultap osultap, thiosultap-sodium, thionazin, thiometon, deet, dieldrin, tetrachlorantraniliprole, tyclopyrazoflor, tetrachlorvinphos, tetradifon, tetranil iprole, tetramethylfluthrin, tetramethrin, tebupirimfos, tebufenozide, tebufenpyrad, tefluthrin, teflubenzuron, demeton-S-methyl, temephos, deltamethrin,Terbufos, doramectin, tralopyril, tralomethrin, 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 starch, binapacryl, pyflubumide, bifenazate, bifenthrin, pymetrozine, pyraclorfos, pyrafluprole, pyridaphenthion, pyridaben, pyridalyl, pyrifluquinazon, pyriprole, pyriproxyfen, pirimicarb, pyrimidifen, pyriminostrobin, pirimiphos-methy1,Pyrethrins, fipronil, fenazaquin, fenamiphos, phenisobromorate, fenitrothion (MEP), fenoxycarb, fenothiocarb, fenothrin, fenobucarb, fensulfothion, fenthion (MPP), phenthoate (phenthoate) PAP), fenvalerate, fenpyroximate, fenpropathrin, fenbendazole, fenmezoditiaz, fosthiazate, formetanate, butathiofos , buprofezin, furathiocarb, prallethrin, fluacrypyrim, furazaindolizine, 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 (propoxur: PHC), flometoquin, alpha-bromadiolone, bromopropylate, beta-cyfluthrin, hexaflumuron, hexythiazox, heptafluthrin, heptenophos, permethrin, benclothiazol az), bendiocarb, benzpyrimoxan, bensultap, benzoximate, benfuracarb, phoxim, phosalone, fosthiazate, fosthietan, phosphamidon, phosphocarb, phosmet (PMP), polynactins, formetanate, formothion, phorate, machine oil, malathion, milbemycin,Milbemycin-A, milbemectin, mecarbam, mesulfenfos, methomyl, metaldehyde, metaflumizone, methamidophos, metam-ammonium, metam-sodium, methiocarb, methidathion: DMTP), methylisothiocyanate, methylneodecanamide, methylparathion, metoxadiazone, methoxychlor, methoxyfenozide, metofluthrin, methoprene, metolcarb, meperfluthrin, n), mevinphos, monocrotophos, monosultap, momfluorothrin, lambda-cyhalothrin, ryanodine, lufenuron, rescalure, resmethrin, lepimectin, rotenone, levamisol hydrochloride, fenbutatin oxide, morantel tartarate, methyl bromide, tricyclohexyltin hydroxide, calcium cyanamide, calcium sulfur Examples include polysulfide, sulfur, and nicotine sulfate.

[0197] Examples of agricultural and horticultural fungicides used for similar purposes include aureofungin, azaconazole, azithiram, acypetacs, acibenzolar, acibenzolar-S-methyl, azoxystrobin, anilazine, amisulbrom, ampropylfos, ametoctradin, and allyl alcohol. alcohol), aldimorph, amobam, isotianil, isovaledione, isopyrazam, isofetamide, isoflutipram, isoprothiolane, ipconazole, ipfentrifluconazole, ipflufenoquin, iprodione, iprovalicarb, iprobenfos, imazalil, iminoctadine, metam (metam), iminoctadine-albesilate, iminoctadine-triacetate, imibenconazole, inpyrfluxam, uniconazole, uniconazole-P, echlomezole, edifenphos, etaconazole, etaboxam, ethirimol, etem, ethoxyquin, etridiazole, enestroburin,enoxastrobin, epoxiconazole, oxadixyl, oxathiapiprolin, oxycarboxin, copper-8-quinolinolate, oxytetracycline, copper-oxinate, oxpoconazole, oxpoconazole-fumarate, oxolinic acid acid), octhilinone, ofurace, orysastrobin, carbam, metam-sodium, kasugamycin, carbamorph, carpropamid, carbendazim, carboxin, carvone, quinazamid, quinacetol, quinoxyfen, quinofumelin, chinomethionate , quinomethionate), captafol, captan, kiralaxyl, quinconazole, quintozene, guazatine, cufraneb, cuprobam, coumoxystrobin, glyodin, griseofulvin, climbazole, cresol, kresoxim-methyl, chlozolinate, clotrimazole, chlobenthiazone, chloraniformethan, chloranil,Chlorquinox, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, chloroneb, salicylanilide, zarilamid, cyazofamid, diethyl pyropate carbonate pyrocarbonate, diethofencarb, cyclafuramid, diclocymet, dichlozoline, diclobutrazol, cyclobutrifluram, dichlofluanid, cycloheximide, dichlobentiazox, diclomezine, dicloran, dichlorophen, dicloron, disulfiram, ditalimfos, dithianon, di Niconazol (diniconazole), diniconazole-M (diniconazole-M), zineb (zineb), dinocap (dinocap), dinocton (dinosulfon), dinoterbone (dinoterbon), dinobuton (dinobuton), dinopenton (dinopenton), dipymetitrone (dipyrithione), diphenylamine (diphenylamine), difenoconazole (difenoconazole), cyflufenamid (cyflufenamid), diflumetorim (diflumetorim), cyproconazole (cyproconazole), cyprodinil (cyprodinil), cyprofuram (cyprofuram),Cypendazole, simeconazole, dimethirimol, dimethomorph, cymoxanil, dimoxystrobin, ziram, silthiofam, streptomycin, spiroxamine, sultropen, sedaxane, zoxamide, dazomet, thiadiazin, tiadinil, thiadifluor, thiadifluoro, abendazole, tioximid, thiochlorfenphim, thiophanate, thiophanate-methyl, thifluzamide, thicyofen, thioquinox, thiram, decaphentin, tecnazene, tecloftalam, tecoram, tetraconazole, debacarb, dehydroacetic acid acid), tebuconazole, tebufloquin, dodicin, dodine, dodecylbenzenesulfonic acid bisethylenediamine copper complex salt (II) (DBEDC), dodemorph, drazoxolon, triadimenol, triadimefon, triazbutil, triazoxide, triamiphos, triarimol, trichlamide, triclopyricarb, tricyclazole,Triticonazole, tridemorph, tributyltin oxide, triflumizole, trifloxystrobin, triforine, tolylfluanid, tolclofos-methyl, tolprocarb, natamycin, nabam, nitrostyrene, nitrothal-isopropyl, nuarimol, copper nonylphenol sulfonate, halacrinate, validamycin, valifenalate, harpin protein protein), picarbutrazox, bixafen, picoxystrobin, picobenzamide, pydiflumetofen, bithionol, bitertanol, hydroxyisoxazole, hydroxyisoxazole-potassium, binapacryl, biphenyl , piperalin, hymexazol, pyraoxystrobin, pyracarbolid, pyraclostrobin, pyraziflumid, pyrazophos, pyrapropoyne, pyrametostrobin, pyriophenone, pyridinitril, pyridiflumetofen,pyrisoxazole, pyridachlometyl, pyrifenox, pyribencarb, pyriminostrobin, pyrimethanil, pyroxychlor, pyroxyfur, pyroquilon, vinclozolin, ferbam, famoxadone ), fenapanil, fenamidone, fenaminosulf, phenaminestrobin, fenarimol, fenitropan, fenoxanil, ferimzone, ferbam, fentin, fenpiclonil, fenpicoxamid, fenpyrazamine ( fenpyrazamine, fenbuconazole, fenfuram, fenpropidin, fenpropimorph, fenhexamid, phthalide, buthiobate, butylamine, bupirimate, fuberidazole, blasticidin-S, furami Topir (furametpyr), furalaxyl, fluacrypyrim, fluazinam, fluindapyr, fluoxastrobin, fluoxapiprolin, fluoxytioconazole, fluotrimazole, fluopicolide, fluopimomide,fluopyram, fluoroimide, furcarbanil, fluxapyroxad, fluquinconazole, fluconazole, furconazole-cis, fludioxonil, flusilazole, flusulfamide, flutianil, flu Flutolanil, flutriafol, flufenoxadiazam, flufenoxystrobin, furfural, flubeneteram, furmecyclox, flumetylsulforim, flumetover, flumorph, proquinazid, promethazine, Prochloraz, procymidone, prothiocarb, prothioconazole, pronitridine, propamocarb, propiconazole, propineb, furophanate, probenazole, bromuconazole, florylpicoxamide ( florylpicoxamid, hexachlorobutadiene, hexaconazole, hexylthiofos, bethoxazin, benalaxyl, benalaxyl-M, benodanil, benomyl, pefurazoate, benquinox, penconazole,benzamorf, pencycuron, benzohydroxamic acid, benzovindiful, benzovindiflupyr, bentaluron, benthiazole, benthiavalicarb, benthiavalicarb-isopropyl, penthiopyrad, penflufen, boscalid, phosdiphen, fosetyl, fosetyl-aluminum, polyoxins, polyoxorim, polycarbamate, folpet, formaldehyde, machine oil oil), maneb, mancozeb, mandipropamid, mandestrobin, myclozolin, myclobutanil, mildiomycin, milneb, mecarbinzid, methasulfocarb, metazoxolone, metam, metam-sodium, metalaxyl, metalaxyl-M, metarylpicoxamid, metiram, methyl isothiocyanateisothiocyanate, methyl dinocap, methyltetraprole, metconazole, metsulfovax, metofuroxam, metominostrobin, metrafenone, mepanipyrim, mefenoxam, mefentrifluconazole, meptyldinocap, mepronil, mebenil, methyl iodide, rabenzazole, methyl bromide, benzalkonium chloride, basic copper chloride, basic copper sulfate Examples of suitable disinfectants include inorganic disinfectants such as sodium hypochlorite, cupric hydroxide, wettable sulfur, calcium polysulfide, potassium hydrogen carbonate, sodium hydrogen carbonate, inorganic sulfur, copper compounds such as copper sulfate anhydride, nickel dimethyldithiocarbamate, and 8-hydroxyquinoline copper, zinc sulfate, and copper sulfate pentahydrate.

[0198] Similarly, herbicides such as 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 thioethyl, MCPB, ioxynil, aclonifen, azafenidin, din), acifluorfen, aziprothrin, azimsulfuron, asulam, acetochlor, atrazine, atraton, anisuron, anilofos, aviglycine, abscisic acid acid), amicarbazone, amidosulfuron, amitrole, aminocyclopyrachlor, aminopyralid, amivudine, amiprophos-methyl, ametridione, ametryn, alachlor, allidochlor, alloxydim, arorac, iofensulfuron ensulfuron, isouron, isocarbamide, isoxachlortole, isoxapyrifop, isoxaflutole, isoxaben, isocil, isonoruron, isoproturon, isopropalin, isopolinate, isomethiozin, inabenfide, ipazine,Ipfencarbazone, iprimidam, imazaquin, imazapic, imazapyr, imazamethapyr, imazamethabenz, imazamethabenz-methyl, imazamox, imazethapyr, imazosulfuron, indaziflam, indanofan, indolebutyric acid acid), uniconazole-P, eglinazine, esprocarb, ethametsulfuron, ethametsulfuron-methyl, ethalfluralin, ethiolate, ethychlozate-ethyl, ethidimuron, ethinofen, ethephon, ethoxysulfuron, ethoxyfen, etnipromid, etofumesate, etho benzanilide, epirifenacil, 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, quinonamide mid), quinclorac, quinmerac, cumyluron, clacyfos, cliodinate, glyphosate, glufosinate, glufosinate-P, credazine, clethodim, cloxyfonac, clodinafop, clodinafop-propal Clodinafop-propargyl, clotoluron, clopyralid, cloproxydim, cloprop, chlorbromuron, clofop, clomazone, chlomethoxynil, chlomethoxyfen, clomeprop, chlorazifop ), chlorazine, chloranocryl, chloramben, cloransulam, cloransulam-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorsulfuron, chlorthal, chlorthiamid,Chlortoluron, chlornitrofen, chlorfenac, chlorfenprop, chlorbufam, chlorphthalim, chlorflurazole, chlorflurenol, chlorprocarb, chlorpropham, chlormequat, chloreturon, chloroxynil, chloroxuron ), chlorotoluron, chloropon, saflufenacil, cyanazine, cyanatryn, di-allate, diuron, diethamquat, dioxopyritrione, dicamba, cycluron, cycloate, cycloxydim, diclosulam, cyclosulfamuron, cyclopyranil , cyclopyrimorate, dicloprop, dicloprop-P, dichlobenil, diclofop, diclofop-methyl, dichromate, dichloralurea, diquat, cisanilide, disul, siduron, dithiopyr, dinitramine, cinidon-ethyl, dinosam, cinosulfuron, dinoseb, dinoterb,Dinofenate, dinoprop, cyhalofop-butyl, cypyrafluone, diphenamid, difenoxuron, difenopenten, difenzoquat, cybutryne, cyprazine, cyprazole, diflufenican, Diflufenzopyr, dipropetryn, cypromid, cyperquat, gibberellin, simazine, dimexano, dimesulfazet, dimethachlor, dimidazon, dimethametryn, dimethenamid, simetryn ryn, simeton, dimepiperate, dimefuron, cinmethylin, swep, sulglycapin, sulcotrione, sulfalate, sulfentrazone, sulfosulfuron, sulfometuron, sulfometuron-methyl ethyl), secbumeton, sethoxydim, sebuthylazine, terbacil, daimuron, dazomet, dalapon, thiazafluron, thiazopyr, thiaphenacyl, thiencarbazone, thiencarbazone-methyl,Thiocarbazil, thioclorim, thiobencarb, thidiazimin, thidiazuron, thifensulfuron, thifensulfuron-methyl, desmedipham, desmetryn, tetflupyrolimet, tetrafluron n), thenylchlor, tebutam, tebuthiuron, terbumeton, tepraloxydim, tefuryltrione, tembotrione, delaclor, terbacil, terbucarb, terbuchlor, terbuthylazine, terbutryn terbutryn, topramezone, tralkoxydim, triaziflam, triasulfuron, triafamone, tri-allate, trietazine, tricamba, triclopyr, tridiphane, tritac, tritosulfuron, tripira Sulfone, trifludimoxazin, triflusulfuron, triflusulfuron-methyl, trifluralin, trifloxysulfuron, tripropindan, tribenuron, tribenuron-methyl, triphop,Trifopsime, trimeturon, tolpyralate, naptalam, naproanilide, naproamide, nicosulfuron, nitralin, nitrofen, nitrofluorfen, nipyraclofen, neburon, norflurazon lurazon, noruron, barban, paclobutrazol, paraquat, parafluron, haloxydine, haloxifen, haloxyfop, haloxyfop-P, haloxyfop-methyl, halosafen, halosulfuron, halo Halosulfuron-methyl, bialafos, bixlozone, picloram, picolinafen, bicyclopyrone, bispyribac, bispyribac-sodium, pydanon, pinoxaden, bipyrazone, bifenox, Piperophos, hymexazol, pyraclonil, pyrasulfotole, pyrazoxyfen, pyrazosulfuron, pyrazosulfuron-ethyl, pyrazolate, bilanafos, pyraflufen, pyraflufen-ethyl,Pyriclor, pyridafol, pyrithiobac, pyrithiobac-sodium (pyri, thiobac-sodium, pyridate, pyriftalid, pyributicarb, pyribenzoxim, pyrimisulfan, pyrimisulfuron, pyriminobac-methyl, pyroxasulfone, pyroxsulam, fenasulam, phenisulfam opham, fenuron, fenoxasulfone, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, phenothiol, fenoprop, phenobenzuron, fenquinotrione, fenthiaprop, fenthiacor teracol, fentrazamide, fenpyrazone, phenmedipham, phenmedipham-ethyl, butachlor, butafenacil, butamifos, buthiuron, buthidazole, butyrate, buturon, butenachlor lor), butoxydim, butralin, butroxydim, flazasulfuron, flamprop, furyloxyfen, prinachlor, primisulfuron-methyl, fluazifop, fluazifop-P, fluazifop-butyl,Fluazolate, fluroxypyr, fluothiuron, fluometuron, fluoroglycofen, flurochloridone, fluorodifen, fluoronitrofen, fluoromidine, flucarbazone, flucarbazone-sodium carbazone-sodium, fluchloralin, flucetosulfuron, fluthiacet, fluthiacet-methyl, flupyrsulfuron, flufenacet, flufenican, flufenpyr, flupropacil, flupropanate ), flupoxam, flumioxazin, flumiclorac, flumiclorac-pentyl, flumipropyn, flumezin, fluometuron, flumetsulam, fluridone, flurtamone, fluroxypyr, pretilachlor lachlor, proxan, proglinazine, procyazine, prodiamine, prosulfalin, prosulfuron, prosulfocarb, propaquizafop, propachlor, propazine, propanil, propyzamide,Propisochlor, Prohydrojasmon, Propyrisulfuron, Propham, Profluazol, Profluralin, Prohexadione-calcium, Propoxycarbazone, Propoxycarbazone-sodium, Profoxycarbazone-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, benzip Benzipram, benzylaminopurine, benzthiazuron, benzfendizone, bensulide, bensulfuron-methyl, benzoylprop, benzobicyclon, benzofenap, benzofluor, bentazone,Pentanochlor, benthiocarb, pendimethalin, pentoxazone, benfluralin, benfuresate, fosamine, fomesafen, foramsulfuron, forchlorfenuron, maleic hydrazide hydrazide), mecoprop, mecoprop-P, medinoterb, mesosulfuron, mesosulfuron-methyl, mesotrione, mesoprazine, mesoprotryne, metazachlor, methazole, metazosulfuron, methabenzthiazuron, metamitron, metamifop, metam, metham, methalpropalin, methiuron, methizolin ozolin), methiobencarb, methyldymron, metoxuron, metoslam, metsulfuron, metsulfuron-methyl, metflurazon, metobromuron, metobenzuron, methometon, metolachlor, metribuzin, mepiquat-chloride, mefenacet, mefluidide, monalide, monisouron, monuron,Examples of such an agent include monochloroacetic acid, monolinuron, molinate, morphamquat, iodosulfuron, iodosulfuron-methyl-sodium, iodobonil, iodomethane, lactofen, lancotrione, linuron, rimisoxafen, rimsulfuron, lenacil, rhodethanil, calcium peroxide, and methyl bromide.

[0199] In addition, examples of biological pesticides include virus preparations such as nuclear polyhedrosis virus (NPV), granulosis virus (GV), cytoplasmic polyhedrosis virus (CPV), and entomopoxi virus (EPV); microbial pesticides used as insecticides or nematocides such as Monacrosporium phymatophagum, Steinernema carpocapsae, Steinernema kushidai, and Pasteuria penetrans; and pesticides such as Trichoderma lignorum and Agrobacterium radiobacter. Similar effects can be expected by mixing it with microbial pesticides used as fungicides such as Erwinia carotovora (Neutrophil gram-negative bacteria), non-pathogenic Erwinia carotovora (Bacillus subtilis), and biological pesticides used as herbicides such as Xanthomonas campestris.

[0200] Furthermore, as biological pesticides, for example, natural enemies such as Encarsia formosa, Aphidius colemani, Aphidoletes aphidimyza, Diglyphus isaea, Dacnusa sibirica, Phytoseiulus persimilis, Amblyseius cucumeris, Orius sauteri, etc., and Beauveria brongniartii, It is also possible to use it in combination with a microbial pesticide such as E. brongniartii, or a pheromone agent such as (Z)-10-tetradecenyl acetate, (E,Z)-4,10-tetradecenyl acetate, (Z)-8-dodecenyl acetate, (Z)-11-tetradecenyl acetate, (Z)-13-icosen-10-one, or 14-methyl-1-octadecene. EXAMPLES

[0201] Representative examples of the present invention are given below, but the present invention is not limited to these.

[0202] Manufacturing Example 1 Preparation of N-(4-fluorophenyl)-5-hydroxy-3-oxo-1-(4-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridazine-4-carboxamide (compound no. 1-7). [ka]

[0203] Ethyl 5-hydroxy-3-oxo-1-(4-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridazine-4-carboxylate (0.15g, 0.45mmol) was mixed with toluene (5ml), 4-fluoroaniline (0.06g, 0.54mmol) was added dropwise thereto, and the mixture was stirred for 2 hours while removing ethanol using a Dean-Stark apparatus under heating and reflux. After cooling the reaction solution, the reaction crude product obtained by concentrating under reduced pressure was purified by silica gel column chromatography to obtain the title compound (0.05g). Yield: 28% Physical properties: Melting point 65-70℃

[0204] Manufacturing Example 2 Preparation of N-(4-fluorophenyl)-1-(6-chloropyridin-3-yl)-5-hydroxy-3-oxo-1,2,3,6-tetrahydropyridazine-4-carbothioamide (compound no. 2-3). [ka]

[0205] 1-(6-chloropyridin-3-yl)-5-hydroxy-1,6-dihydropyridazin-3(2H)-one (0.10 g, 0.44 mmol) was dissolved in dimethylformamide (3.0 mL), and cesium carbonate (0.17 g, 0.53 mmol) was added thereto, followed by slowly dropping 4-fluorophenyl isothiocyanate (0.11 g, 0.71 mmol) and stirring 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 to separate the layers. The aqueous layer was extracted twice with ethyl acetate (10 mL), and the organic layers were combined and washed once with saturated saline (10 mL), and then dried by adding anhydrous sodium sulfate. The solution was concentrated under reduced pressure to obtain a crude product, which was purified by silica gel column chromatography to obtain the title compound (0.02 g). Yield: 12% Physical properties: Melting point 230-233℃

[0206] Manufacturing Example 3 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) [ka]

[0207] Lawesson's reagent (0.056 g, 0.14 mmol) was added to 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), and the mixture was stirred for 2 hours under heating and reflux. After completion of the reaction, the reaction solution was concentrated using a rotary evaporator. The resulting residue was dissolved in ethyl acetate and purified by silica gel chromatography. The resulting crystals were washed with normal hexane / methyl tertiary butyl and collected by filtration to obtain the title compound (0.055 g, 0.13 mmol). Yield: 52% Physical properties: Melting point 182-184℃

[0208] Reference Example 1 Preparation of 1-diphenylmethylene-2-(4-trifluoromethylphenyl)hydrazine. [ka]

[0209] 4-Trifluoromethylphenylhydrazine (5.28 g, 30.0 mmol) was dissolved in ethanol (50 mL), and benzophenone (5.28 g, 29 mmol) and acetic acid (5.40 g, 90 mmol) were added thereto, followed by stirring for 2 hours under heating and reflux. After cooling the reaction solution, 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). Yield: 92%

[0210] Reference Example 2 Preparation of methyl 2-{2-diphenylmethylene-1-(4-trifluoromethylphenyl)hydrazinyl} acetate [ka]

[0211] 60% sodium hydride (1.2g, 30.0mmol) was suspended in dimethylacetamide (20mL), and a solution of 1-diphenylmethylene-2-(4-trifluoromethylphenyl)hydrazine (8.51g, 25.0mmol) in dimethylacetamide (10mL) was slowly added dropwise under ice cooling, and the mixture was stirred for 10 minutes. Methyl bromoacetate (4.97g, 32.5mmol) was slowly added dropwise thereto, and the mixture was warmed to room temperature and stirred for 2 hours. The solution after the reaction was slowly poured into ice water (30mL), and the aqueous layer was extracted three times with ethyl acetate (30mL). The organic layers obtained were combined, washed once with saturated saline (30mL), and dried by adding anhydrous sodium sulfate. The solution was concentrated under reduced pressure to obtain a crude reaction product, which was purified by silica gel column chromatography to obtain the title compound (7.0g). Yield: 68%

[0212] Reference Example 3 Preparation of methyl 2-{1-(4-trifluoromethylphenyl)hydrazinyl} acetate [ka]

[0213] Methyl 2-{2-diphenylmethylene-1-(4-trifluoromethylphenyl)hydrazinyl}acetate (6.58g, 15.7mmol) was dissolved in a mixture of ethanol (50mL) and 2-methyltetrahydrofuran (10mL), and concentrated hydrochloric acid (10mL) was added dropwise thereto and stirred at room temperature for 3 hours. The solution after the reaction was concentrated under reduced pressure, and then water (50mL) was added, and potassium carbonate was added to make it weakly basic. The aqueous layer was extracted three times with ethyl acetate (50mL), and the obtained organic layers were combined, washed once with saturated saline (50mL), 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 (3.65g). Yield: 94%

[0214] Reference Example 4 Preparation of ethyl 3-{2-(2-methoxy-2-oxoethyl)-2-(4-trifluoromethylphenyl)hydrazinyl}-3-oxopropionate [ka]

[0215] Methyl 2-{1-(4-trifluoromethylphenyl)hydrazinyl}acetate (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 the mixture was stirred at room temperature for 2 hours. Water (50mL) and chloroform (50mL) were added to the reaction solution, and the mixture was separated. The organic layer obtained was washed once with 10% hydrochloric acid (50mL) and once with saturated saline (50mL), and dried by adding anhydrous sodium sulfate. The reaction crude product obtained by concentrating the solution under reduced pressure was purified by silica gel column chromatography to obtain the title compound (3.9g). Yield: 73%

[0216] Reference Example 5 Preparation of ethyl 5-hydroxy-3-oxo-1-(4-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridazine-4-carboxylate (Compound No. 5-29) [ka]

[0217] Ethyl 3-{2-(2-methoxy-2-oxoethyl)-2-(4-trifluoromethylphenyl)hydrazinyl}-3-oxopropionate (1.1 g, 3.0 mmol) was dissolved in ultra-dehydrated ethanol (10 mL) under an argon atmosphere, and 20% sodium ethoxide in ethanol solution (2.04 g, 6.0 mmol) was slowly added dropwise thereto, and the mixture was stirred at 60 ° C for 1 hour. After cooling the reaction solution, water (30 mL) and ethyl acetate (20 mL) were added to the reaction crude product obtained by concentrating under reduced pressure, and the mixture was separated. 10% hydrochloric acid was added to the obtained aqueous layer to make it acidic. The aqueous layer was extracted three times with ethyl acetate (30 mL), and the organic layers were combined and washed once with saturated saline (30 mL), and dried by adding anhydrous sodium sulfate. The solution was concentrated under reduced pressure, and the precipitated crystals were washed with a mixed solution of normal hexane and ethyl acetate to obtain the title compound (0.35 g). Yield: 35%

[0218] Reference Example 6 Preparation of 5-hydrazinyl-2-trifluoromethylpyridine. [ka]

[0219] 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 over 30 minutes while adjusting the temperature of the reaction solution to not exceed 10 ° C. under ice cooling. After the dropwise addition, the mixture was stirred at the same temperature for 30 minutes. In a separately prepared reaction vessel, tin(II) chloride (22.75 g, 120.0 mmol) was dissolved in concentrated hydrochloric acid (20 mL). The solution of the diazonium salt prepared above was slowly added dropwise over 30 minutes while adjusting the temperature of the reaction solution to not exceed 10 ° C. under ice cooling. After the dropwise addition, the mixture was warmed to room temperature and stirred for 2 hours. The solution after the reaction was made basic by adding an aqueous sodium hydroxide solution under ice cooling, and then filtered through Celite. Ethyl acetate (200 mL) was added to the obtained filtrate and separated. The aqueous layer was extracted twice with ethyl acetate (100 mL), and the combined organic layers were washed once with saturated saline (100 mL), and then dried by adding anhydrous sodium sulfate. The solution was concentrated under reduced pressure to obtain a crude reaction product, which was purified by silica gel column chromatography to obtain the title compound (7.0 g). Yield: 66%

[0220] Reference Example 7 Preparation of 2-hydrazinyl-5-trifluoromethylpyridine. [ka]

[0221] 2-Bromo-5-trifluoromethylpyridine (4.52 g, 20.0 mmol) was dissolved in ethanol (30 mL), and hydrazine monohydrate (8.0 g, 160.0 mmol) was slowly added dropwise thereto, followed by stirring under heating and reflux for 3 hours. The solution after the reaction was allowed to cool, and then water (10 mL) was added and concentrated under reduced pressure. Water (20 mL) and ethyl acetate (30 mL) were added to the resulting concentrate and the liquids were separated. The aqueous layer was extracted twice with ethyl acetate (30 mL), and the organic layers were combined and washed once with saturated saline (30 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 (3.50 g). Yield: 99%

[0222] Reference Example 8 Preparation of 1-(6-chloropyridin-3-yl)-5-hydroxy-1,6-dihydropyridazin-3(2H)-one (Compound No. 4-28) [ka]

[0223] 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 mixture of acetonitrile (10 mL) and water (1 mL) and stirred under reflux for 2 hours. The solution was cooled and then concentrated under reduced pressure to obtain a crude product, which was purified by silica gel column chromatography to obtain the title compound (0.58 g). Yield: 76%

[0224] Formulation examples are shown below, but the invention is not limited to these. In the formulation examples, parts indicate parts by weight.

[0225] Formulation example 1. Compound of the present invention 10 parts Xylene 70 parts N-Methylpyrrolidone 10 parts Polyoxyethylene nonylphenyl ether Mixture with calcium alkylbenzene sulfonate 10 parts The above ingredients are mixed and dissolved uniformly to prepare an emulsion.

[0226] Formulation example 2. Compound of the present invention Part 3 82 parts clay powder 15 parts diatomaceous earth powder The above ingredients are mixed and ground uniformly to obtain a powder.

[0227] Formulation example 3. Compound of the present invention 5 parts 90 parts of bentonite and clay powder mixture Calcium lignosulfonate 5 parts The above ingredients are mixed uniformly, an appropriate amount of water is added, the mixture is kneaded, granulated, and dried to give granules.

[0228] Formulation example 4. Compound of the present invention 20 parts Kaolin and synthetic highly dispersed silicic acid 75 parts Polyoxyethylene nonylphenyl ether Mixture with calcium alkylbenzene sulfonate 5 parts The above ingredients are mixed uniformly and pulverized to prepare a wettable powder.

[0229] Examples of biological tests are shown below, but the present invention is not limited to these.

[0230] Test Example 1. Insecticidal test against diamondback moth (Plutella xylostella) Adult diamondback moths were released onto Chinese cabbage seedlings to allow them to lay eggs, and two days after release, the Chinese cabbage seedlings with the eggs were immersed for approximately 30 seconds in a chemical solution containing a compound represented by the general formula (1) of the present invention as an active ingredient, diluted to 500 ppm, and then air-dried and placed in a thermostatic chamber at 25°C. Six days after immersion in the chemical solution, the number of hatched insects was counted, and the mortality rate was calculated using the following formula and judged according to the following criteria. 10 insects per section, 3 replicates.

[0231]

number

[0232] Judgment criteria: A... Mortality rate 100% B···Insect death rate 99%~90% C···Insect death rate 89%~80% D···Insect death rate 79%~50% E···Death rate: 49%~0%

[0233] 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, and 1-4 0, 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, 1-73, 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, 1-206, 1-212, 1-215, 1-216, 1-218, 1-221, 1-222, 1-227, 1-229, 1-230, 1-2 33, 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, 1-304 Compounds 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 diamondback moth, rated as A.

[0234] Test Example 2. Insecticidal test against the small brown planthopper (Laodelphax striatella) The compound represented by the general formula (1) of the present invention or a salt thereof was dispersed in water and diluted to a 500 ppm drug solution. Rice seedlings (variety: Nipponbare) were immersed in the drug solution for 30 seconds and air-dried, then placed in glass test tubes, inoculated with 10 3rd instar brown planthoppers each, and then plugged with cotton. Eight days after inoculation, the number of live and dead insects was counted, and the corrected mortality rate was calculated from the following formula and judged according to the judgment criteria of Test Example 1.

[0235]

number

[0236] 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, 1-121, 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 ,1-185,1-186,1-187,1-188,1-189,1-190,1-191,1-192,1-193,1-194,1-195,1-196,1-197,1-198,1-199,1-200,1-201,1-202,1-203,1-204,1-2 05, 1-206, 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, 1-31 Compounds 6, 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, 2-15, 2-16, 2-17, 2-18, 2-19, 2-20, 3-1 and 3-2 showed excellent activity against the small brown planthopper, rated as A.

[0237] Test Example 3. Insecticidal test against Frankliniella occidentalis Female adult western flower thrips were inoculated onto kidney bean leaf pieces fixed on an agar medium, and after one day of egg laying, the female adult thrips were removed. After a further three days, the number of hatched larvae on the leaf pieces was counted, and then a liquid of a drug containing the compounds shown in Tables 1 to 5 as active ingredients diluted to 500 ppm was sprayed. Four days after treatment, the number of surviving larvae of this species was counted, and the mortality rate was calculated according to the following formula, and the evaluation criteria of Test Example 1 were followed. Two-run test.

[0238]

number

[0239] 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 ,1-149,1-150,1-151,1-152,1-153,1-154,1-155,1-157,1-158,1-159,1-160,1-167,1-168,1-170,1-172,1-173,1-175,1-176,1-183,1-184,1-185,1-186,1-187,1-188,1-189,1-190,1-191,1-192,1-193,1-194,1-195,1-196,1-197,1-198,1-199,1-200,1-201,1-202,1-203,1-204,1-205,1-206,1 5, 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, 1-2 14, 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, 1-301, 1-302, 1-303,Compounds 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, rated as A. [Industrial Applicability]

[0240] The compound of the present invention or a salt thereof has excellent effects as an agricultural and horticultural insecticide.

Claims

1. General formula (1) 【Chemistry 1】 {During the ceremony, R １ teeth, (a1) a hydrogen atom; (a2) (C １ -C ６ ) alkyl group; (a3) (C ２ -C ６ ) alkenyl group; (a4) (C ２ -C ６ ) an alkynyl group; (a5) (C ３ -C ６ ) a cycloalkyl group; (a6) (C １ -C ６ ) an alkoxy group; (a7) Halo (C １ -C ６ ) alkyl group; (a8) (C １ -C ６ ) an alkylcarbonyl group; (a9) (C １ -C ６ ) an alkoxycarbonyl group; (a10) a cyano group, (C １ -C ６ ) alkoxy group and (C ３ -C ６ ) a substituted cycloalkyl group having 1 to 3 substituents on the chain independently selected from the group consisting of cycloalkyl groups (C １ -C ６ ) alkyl group; (a11) a thiazolylmethyl group; (a12) a halogen atom, (C １ -C ６ ) alkyl group and (C １ -C ６ ) a substituted thiazolylmethyl group having, on a ring, 1 to 2 substituents independently selected from the group consisting of an alkoxy group; (a13) a benzyl group; or (a14) a halogen atom, (C １ -C ６ ) alkyl group and (C １ -C ６ ) a substituted benzyl group having, on the ring, 1 to 3 substituents independently selected from the group consisting of alkoxy groups. R ２ teeth, (b1) an aryl group; (b2) a substituted aryl group having, on the ring, one or more substituents independently selected from the substituent group A; (b3) a 5- to 10-membered heterocyclic group; or (b4) represents a substituted 5- to 10-membered heterocyclic group having one or more substituents independently selected from the substituent group A on the ring. However, R ２ (C) is attached to the adjacent atom of the bond atom to the tetrahydropyridazine ring. １ -C ６ ) alkylsulfonyl group, halo(C １ -C ６ ) alkylsulfonyl group, N-(C １ -C ６ ) alkylaminosulfonyl group, N,N-di(C １ -C ６ ) an alkylaminosulfonyl group, and R ６ - (R ７ -N=)O=S group (in the formula, R ６ (C １ -C ６ ) alkyl group, (C ３ -C ６ ) cycloalkyl group, halo(C １ -C ６ ) an alkyl group, or (C １ -C ６ ) Alkoxy (C １ -C ６ ) represents an alkyl group; R ７ is a hydrogen atom, a cyano group, (C １ -C ６ ) alkyl group, (C ３ -C ６ ) cycloalkyl group, halo(C １ -C ６ ) alkyl group, (C ２ -C ６ ) alkylcarbonyl group, or halo(C ２ -C ６ ) denotes an alkylcarbonyl group. ) is unsubstituted. R ３ teeth, (c1) a hydrogen atom; (c2) (C １ -C ６ ) alkyl group; (c3) (C ３ -C ６ ) a cycloalkyl group; (c4) (C １ -C ６ ) an alkoxy group; or (c5) (C １ -C ６ ) an alkylcarbonyl group. R ４ teeth, (d1) (C １ -C ６ ) alkyl group; (d2) (C ２ -C ６ ) alkenyl group; (d3) (C ２ -C ６ ) an alkynyl group; (d4) (C ３ -C ６ ) a cycloalkyl group; (d5) Halo (C １ -C ６ ) alkyl group; (d6) Halo (C ２ -C ６ ) alkenyl group; (d7) Halo (C ２ -C ６ ) an alkynyl group; (d8) a substituted group having 1 to 3 substituents independently selected from the substituent group B (C １ -C ６ ) alkyl group; (d9) A substituted ring having 1 to 3 substituents independently selected from the substituent group C (C ３ -C ６ ) a cycloalkyl group; (d10) (C １ -C ６ ) an alkylsulfonyl group; (d11) N-(C １ -C ６ ) an alkylsulfamoyl group; (d12) a phenyl group; (d13) a substituted phenyl group having, on the ring, 1 to 5 substituents independently selected from substituent group D; (d14) Phenyl (C １ -C ６ ) alkyl group; (d15) Substituted phenyl having 1 to 5 substituents independently selected from the substituent group D on the ring (C １ -C ６ ) alkyl group; (d16) a pyridyl group; (d17) a substituted pyridyl group having, on the ring, 1 to 4 substituents independently selected from substituent group D; (d18) a pyridazinyl group; (d19) a substituted pyridazinyl group having, on the ring, 1 to 3 substituents independently selected from substituent group D; (d20) a pyrimidinyl group; (d21) a substituted pyrimidinyl group having, on the ring, 1 to 3 substituents independently selected from substituent group D; (d22) a pyrazinyl group; (d23) a substituted pyrazinyl group having, on the ring, 1 to 3 substituents independently selected from substituent group D; (d24) a pyrazolyl group; (d25) a substituted pyrazolyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group D; (d26) an isoxazolyl group; (d27) a substituted isoxazolyl group having, on the ring, 1 to 2 substituents independently selected from substituent group D; (d28) an isothiazolyl group; (d29) a substituted isothiazolyl group having, on the ring, 1 to 2 substituents independently selected from substituent group D; (d30) an oxazolyl group; (d31) a substituted oxazolyl group having, on the ring, 1 to 2 substituents independently selected from substituent group D; (d32) a thiazolyl group; (d33) a substituted thiazolyl group having, on the ring, 1 to 2 substituents independently selected from substituent group D; (d34) a triazolyl group; (d35) a substituted triazolyl group having, on the ring, 1 to 2 substituents independently selected from substituent group D; (d36) a thiadiazolyl group; (d37) a substituted thiadiazolyl group having, on the ring, one substituent independently selected from substituent group D; (d38) a tetrazolyl group; (d39) a substituted tetrazolyl group having on the ring one substituent selected from the group consisting of substituent group D, each independently selected from the group consisting of: (d40) a triazinyl group; (d41) a substituted triazinyl group having, on the ring, 1 to 2 substituents independently selected from substituent group D; (d42) Frill (C １ -C ６ ) alkyl group; (d43) Substituted furyl (C １ -C ６ ) alkyl group; (d44) Thienyl (C １ -C ６ ) alkyl group; (d45) Substituted thienyl (C １ -C ６ ) alkyl group; (d46) a quinolinyl group; (d47) a substituted quinolinyl group having, on the ring, 1 to 6 substituents independently selected from substituent group D; (d48) benzothiazolyl group; (d49) a substituted benzothiazolyl group having, on the ring, 1 to 4 substituents independently selected from substituent group D; (d50) Pyridyl (C １ -C ６ ) alkyl group; (d51) Substituted pyridyl (C １ -C ６ ) alkyl group; (d52) Pyrazinyl (C １ -C ６ ) alkyl group; (d53) Substituted pyrazinyl having 1 to 3 substituents independently selected from the substituent group D on the ring (C １ -C ６ ) alkyl group; (d54) naphthyl group; (d55) a substituted naphthyl group having, on the ring, 1 to 7 substituents independently selected from the substituent group D; (d56) tetrahydronaphthyl; or (d57) represents a substituted tetrahydronaphthyl group having, on the ring, 1 to 10 substituents each independently selected from substituent group D. X and Y each independently represent an oxygen atom or a sulfur atom. Substituent group A is (e1) a halogen atom; (e2) a cyano group; (e3) a nitro group; (e4) a hydroxyl group; (e5) a carboxyl group; (e6) (C １ -C ６ ) alkyl group; (e7) (C ２ -C ６ ) alkenyl group; (e8) (C ２ -C ６ ) an alkynyl group; (e9) (C １ -C ６ ) an alkoxy group; (e10) (C ３ -C ６ ) a cycloalkyl group; (e11) (C １ -C ６ ) an alkylthio group; (e12) (C １ -C ６ ) an alkylsulfinyl group; (e13) (C １ -C ６ ) an alkylsulfonyl group; (e14) Halo (C １ -C ６ ) alkyl group; (e15) Halo (C ２ -C ６ ) alkenyl group; (e16) Halo (C ２ -C ６ ) an alkynyl group; (e17) Halo (C １ -C ６ ) an alkoxy group; (e18) Halo (C ３ -C ６ ) a cycloalkyl group; (e19) Halo (C １ -C ６ ) an alkylthio group; (e20) Halo (C １ -C ６ ) an alkylsulfinyl group; (e21) Halo (C １ -C ６ ) an alkylsulfonyl group; (e22) (C １ -C ６ ) an alkylcarbonylamino group; (e23) Halo (C １ -C ６ ) an alkylcarbonylamino group; (e24) (C １ -C ６ ) an alkylsulfonylamino group; (e25) Halo (C １ -C ６ ) an alkylsulfonylamino group; (e26) SF ５ base; (e27) (C １ -C ６ ) Alkoxy (C １ -C ６ ) alkyl group; (e28) N-(C １ -C ６ ) an alkylcarboxamide group; (e29) N-halo (C １ -C ６ ) an alkylcarboxamide group; (e30) oxadiazolyl group; (e31) halogen atom, cyano group, (C １ -C ６ ) alkyl group, (C １ -C ６ ) an alkoxy group, (C ３ -C ６ ) a cycloalkyl group, (C １ -C ６ ) an alkylthio group, (C １ -C ６ ) an alkylsulfinyl group, (C １ -C ６ ) alkylsulfonyl group, halo(C １ -C ６ ) alkyl group and halo(C １ -C ６ ) a substituted oxadiazolyl group having one substituent on the ring independently selected from the group consisting of an alkoxy group; (e32) (C １ -C ６ ) an alkoxycarbonyl group; (e33) A halogen atom, a phenyl group, or (C) formed by two adjacent substituents taken together １ -C ６ ) a methylenedioxy group optionally substituted by 1 to 2 substituents selected from the group consisting of alkyl groups; (e34) N-(C １ -C ６ ) an alkylaminosulfonyl group; (e35) N,N-di(C １ -C ６ ) an alkylaminosulfonyl group; (e36) R ６ - (R ７ -N=)O=S group (in the formula, R ６ (C １ -C ６ ) alkyl group, (C ３ -C ６ ) cycloalkyl group, halo(C １ -C ６ ) an alkyl group, or (C １ -C ６ ) Alkoxy (C １ -C ６ ) represents an alkyl group; R ７ is a hydrogen atom, a cyano group, (C １ -C ６ ) alkyl group, (C ３ -C ６ ) cycloalkyl group, halo(C １ -C ６ ) alkyl group, (C ２ -C ６ ) alkylcarbonyl group, or halo(C ２ -C ６ ) represents an alkylcarbonyl group; and (e37) halogen atom, cyano group, (C １ -C ６ ) alkyl group, (C １ -C ６ ) alkoxy group and (C １ -C ６ ) a substituted (C) alkylcarbonyl group having 1 to 3 substituents on the ring, each independently selected from the group consisting of ３ -C ６ ) consisting of a cycloalkyl group. Substituent group B is (f1) a cyano group; (f2) (C ３ -C ６ ) a cycloalkyl group; (f3) (C １ -C ６ ) an alkoxy group; (f4) (C １ -C ６ ) an alkylthio group; (f5) (C １ -C ６ ) an alkylsulfinyl group; (f6) (C １ -C ６ ) an alkylsulfonyl group; (f7) Halo (C ３ -C ６ ) a cycloalkyl group; (f8) Halo (C １ -C ６ ) an alkoxy group; (f9) Halo (C １ -C ６ ) an alkylthio group; (f10) Halo (C １ -C ６ ) an alkylsulfinyl group; (f11) Halo (C １ -C ６ ) an alkylsulfonyl group; (f12) a carboxamide group; and (f13) Consists of a phenylcarbonyl group. Substituent group C is (g1) a cyano group; (g2) (C １ -C ６ ) alkyl group; (g3) (C ３ -C ６ ) a cycloalkyl group; (g4) (C １ -C ６ ) an alkoxy group; (g5) (C １ -C ６ ) an alkylthio group; (g6) (C １ -C ６ ) an alkylsulfinyl group; (g7) (C １ -C ６ ) an alkylsulfonyl group; (g8) Halo (C ３ -C ６ ) a cycloalkyl group; (g9) Halo (C １ -C ６ ) an alkoxy group; (g10) Halo (C １ -C ６ ) an alkylthio group; (g11) Halo (C １ -C ６ ) an alkylsulfinyl group; (g12) Halo (C １ -C ６ ) an alkylsulfonyl group; (g13) Halo (C １ -C ６ ) alkyl group; (g14) a carboxamide group; (g15) (C ２ -C ６ ) alkynyl groups; and (g16) Consists of a phenyl group. Substituent group D is (h1) a halogen atom; (h2) a cyano group; (h3) hydroxyl group; (h4) a carboxyl group; (h5) (C １ -C ６ ) alkyl group; (h6) (C １ -C ６ ) an alkoxy group; (h7) (C ３ -C ６ ) a cycloalkyl group; (h8) (C １ -C ６ ) an alkylthio group; (h9) (C １ -C ６ ) an alkylsulfinyl group; (h10) (C １ -C ６ ) an alkylsulfonyl group; (h11) Halo (C １ -C ６ ) alkyl group; (h12) Halo (C １ -C ６ ) an alkoxy group; (h13) Halo (C ３ -C ６ ) a cycloalkyl group; (h14) Halo (C １ -C ６ ) an alkylthio group; (h15) Halo (C １ -C ６ ) an alkylsulfinyl group; (h16) Halo (C １ -C ６ ) an alkylsulfonyl group; (h17) (C １ -C ６ ) an alkoxycarbonyl group; (h18) N-(C １ -C ６ ) an alkylcarboxamide group; (h19) N-Halo (C １ -C ６ ) an alkylcarboxamide group; (h20) A halogen atom, a phenyl group, and (C １ -C ６ ) a methylenedioxy group optionally substituted by 1 to 2 substituents selected from the group consisting of alkyl groups; (h21) nitro group; (h22) amino group; and (h23) A compound represented by the formula:

2. R １ , R ３ , R ４ X, Y, and the substituent groups A, B, C, and D are the same as those in claim 1; R ２ but, (b5) a phenyl group; (b6) a substituted phenyl group having, on the ring, 1 to 5 substituents independently selected from the substituent group A; (b7) a pyridyl group; (b8) a substituted pyridyl group having, on the ring, 1 to 4 substituents independently selected from the substituent group A; (b9) a pyridazinyl group; (b10) a substituted pyridazinyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b11) a pyrimidinyl group; (b12) a substituted pyrimidinyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b13) a pyrazinyl group; (b14) a substituted pyrazinyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b15) a furyl group; (b16) a substituted furyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b17) a thienyl group; (b18) a substituted thienyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b19) an isoxazolyl group; (b20) a substituted isoxazolyl group having, on the ring, 1 to 2 substituents independently selected from the substituent group A; (b21) an oxazolyl group; (b22) a substituted oxazolyl group having, on the ring, 1 to 2 substituents independently selected from the substituent group A; (b23) a pyrazolyl group; (b24) a substituted pyrazolyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b25) an imidazolyl group; (b26) a substituted imidazolyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b27) a triazolyl group; (b28) a substituted triazolyl group having, on the ring, 1 to 2 substituents independently selected from the substituent group A; (b29) a thiazolyl group; (b30) a substituted thiazolyl group having, on the ring, 1 to 2 substituents independently selected from the substituent group A; (b31) an isothiazolyl group; (b32) a substituted isothiazolyl group having, on the ring, 1 to 2 substituents independently selected from the substituent group A; (b33) a thiadiazolyl group; (b34) a substituted thiadiazolyl group having, on the ring, one substituent independently selected from the substituent group A; (b35) an imidazopyridyl group; (b36) a substituted imidazopyridyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b37) a quinoxalinyl group; (b38) a substituted quinoxalinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b39) a benzoxazolyl group; (b40) a substituted benzoxazolyl group having, on the ring, 1 to 4 substituents independently selected from the substituent group A; (b41) a benzimidazolyl group; (b42) a substituted benzimidazolyl group having 1 to 5 substituents 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 quinolinyl group; (b48) a substituted quinolinyl group having 1 to 6 substituents independently selected from the substituent group A on the ring; (b49) naphthyl group; (b50) a substituted naphthyl group having 1 to 7 substituents independently selected from the substituent group A on the ring; (b51) a triazinyl group; (b52) a substituted triazinyl group having 1 to 2 substituents independently selected from the substituent group A on the ring; (b53) a pyrrolyl group; (b54) a substituted pyrrolyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b55) a tetrazolyl group; (b56) a substituted tetrazolyl group having one substituent independently selected from the substituent group A on the ring; (b57) an oxadiazonyl group; (b58) a substituted oxadiazonyl group having one substituent independently selected from the substituent group A on the ring; (b59) 2-oxopyridyl group; (b60) a substituted 2-oxopyridyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b61) a benzofuranyl group; (b62) a substituted benzofuranyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b63) a benzoisoxazolyl group; (b64) a substituted benzoisoxazolyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b65) a benzothienyl group; (b66) a substituted benzothienyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b67) a benzoisothiazolyl group; (b68) a substituted benzisothiazolyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b69) an indolyl group; (b70) a substituted indolyl group having 1 to 6 substituents independently selected from the substituent group A on the ring; (b71) an isoindolyl group; (b72) a substituted isoindolyl group having 1 to 6 substituents independently selected from the substituent group A on the ring; (b73) indazolyl group; (b74) a substituted indazolyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b75) a benzotriazolyl group; (b76) a substituted benzotriazolyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b77) a furopyridyl group; (b78) a substituted furopyridyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b79) a thienopyridyl group; (b80) a substituted thienopyridyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b81) an indolizinyl group; (b82) a substituted indolizinyl group having 1 to 6 substituents independently selected from the substituent group A on the ring; (b83) a pyrrolopyridyl group; (b84) a substituted pyrrolopyridyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b85) a pyrrolopyrimidinyl group; (b86) a substituted pyrrolopyrimidinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b87) an oxazolopyridyl group; (b88) a substituted oxazolopyridyl group having 1 to 3 substituents independently selected from the substituent group A on the ring; (b89) an isoxazolopyridyl group; (b90) a substituted isoxazolopyridyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b91) an isothiazolopyridyl group; (b92) a substituted isothiazolopyridyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b93) an imidazopyrimidinyl group; (b94) a substituted imidazopyrimidinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b95) a pyrazolopyridyl group; (b96) a substituted pyrazolopyridyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b97) a pyrazolopyrimidinyl group; (b98) a substituted pyrazolopyrimidinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b99) a triazolopyridyl group; (b100) a substituted triazolopyridyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b101) a triazolopyrimidinyl group; (b102) a substituted triazolopyrimidinyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b103) an isoquinolinyl group; (b104) a substituted isoquinolinyl group having 1 to 6 substituents independently selected from the substituent group A on the ring; (b105) a cinnolinyl group; (b106) a substituted cinnolinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b107) a phthalazinyl group; (b108) a substituted phthalazinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b109) a quinazolinyl group; (b110) a substituted quinazolinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b111) a naphthyridinyl group; or (b112) The compound according to claim 1, which is a substituted naphthyridinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring, or a salt thereof.

3. R １ but, (a1) a hydrogen atom; (a2) (C １ -C ６ ) alkyl group; or (a4) (C ２ -C ６ ) an alkynyl group; R ２ but, (b5) a phenyl group; (b6) a substituted phenyl group having, on the ring, 1 to 5 substituents independently selected from the substituent group A; (b7) a pyridyl group; (b8) a substituted pyridyl group having, on the ring, 1 to 4 substituents independently selected from the substituent group A; (b9) a pyridazinyl group; (b10) a substituted pyridazinyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b11) a pyrimidinyl group; (b12) a substituted pyrimidinyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b13) a pyrazinyl group; (b14) a substituted pyrazinyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b15) a furyl group; (b16) a substituted furyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b17) a thienyl group; (b18) a substituted thienyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b19) an isoxazolyl group; (b20) a substituted isoxazolyl group having, on the ring, 1 to 2 substituents independently selected from the substituent group A; (b21) an oxazolyl group; (b22) a substituted oxazolyl group having, on the ring, 1 to 2 substituents independently selected from the substituent group A; (b23) a pyrazolyl group; (b24) a substituted pyrazolyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b25) an imidazolyl group; (b26) a substituted imidazolyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b27) a triazolyl group; (b28) a substituted triazolyl group having, on the ring, 1 to 2 substituents independently selected from the substituent group A; (b29) a thiazolyl group; (b30) a substituted thiazolyl group having, on the ring, 1 to 2 substituents independently selected from the substituent group A; (b31) an isothiazolyl group; (b32) a substituted isothiazolyl group having, on the ring, 1 to 2 substituents independently selected from the substituent group A; (b33) a thiadiazolyl group; (b34) a substituted thiadiazolyl group having, on the ring, one substituent independently selected from the substituent group A; (b35) an imidazopyridyl group; (b36) a substituted imidazopyridyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b37) a quinoxalinyl group; (b38) a substituted quinoxalinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b39) a benzoxazolyl group; (b40) a substituted benzoxazolyl group having, on the ring, 1 to 4 substituents independently selected from the substituent group A; (b41) a benzimidazolyl group; (b42) a substituted benzimidazolyl group having 1 to 5 substituents 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 quinolinyl group; or (b48) a substituted quinolinyl group having 1 to 6 substituents independently selected from the substituent group A on the ring, R ３ but, (c1) a hydrogen atom; or (c2) (C １ -C ６ ) alkyl group, R ４ but, (d1) (C １ -C ６ ) alkyl group; (d2) (C ２ -C ６ ) alkenyl group; (d3) (C ２ -C ６ ) an alkynyl group; (d4) (C ３ -C ６ ) a cycloalkyl group; (d5) Halo (C １ -C ６ ) alkyl group; (d8) a substituted group having 1 to 3 substituents independently selected from the substituent group B (C １ -C ６ ) alkyl group; (d9) A substituted ring having 1 to 3 substituents independently selected from the substituent group C (C ３ -C ６ ) a cycloalkyl group; (d10) (C １ -C ６ ) an alkylsulfonyl group; (d11) N-(C １ -C ６ ) an alkylsulfamoyl group; (d12) a phenyl group; (d13) a substituted phenyl group having, on the ring, 1 to 5 substituents independently selected from substituent group D; (d14) Phenyl (C １ -C ６ ) alkyl group; (d15) Substituted phenyl having 1 to 5 substituents independently selected from the substituent group D on the ring (C １ -C ６ ) alkyl group; (d16) a pyridyl group; (d17) a substituted pyridyl group having, on the ring, 1 to 4 substituents independently selected from substituent group D; (d18) a pyridazinyl group; (d19) a substituted pyridazinyl group having, on the ring, 1 to 3 substituents independently selected from substituent group D; (d20) a pyrimidinyl group; (d21) a substituted pyrimidinyl group having, on the ring, 1 to 3 substituents independently selected from substituent group D; (d22) a pyrazinyl group; (d23) a substituted pyrazinyl group having, on the ring, 1 to 3 substituents independently selected from substituent group D; (d24) a pyrazolyl group; (d25) a substituted pyrazolyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group D; (d26) an isoxazolyl group; (d27) a substituted isoxazolyl group having, on the ring, 1 to 2 substituents independently selected from substituent group D; (d28) an isothiazolyl group; (d29) a substituted isothiazolyl group having, on the ring, 1 to 2 substituents independently selected from substituent group D; (d30) an oxazolyl group; (d31) a substituted oxazolyl group having, on the ring, 1 to 2 substituents independently selected from substituent group D; (d32) a thiazolyl group; (d33) a substituted thiazolyl group having, on the ring, 1 to 2 substituents independently selected from substituent group D; (d34) triazolyl group; (d35) a substituted triazolyl group having, on the ring, 1 to 2 substituents independently selected from substituent group D; (d36) a thiadiazolyl group; (d37) a substituted thiadiazolyl group having, on the ring, one substituent independently selected from substituent group D; (d38) a tetrazolyl group; (d39) a substituted tetrazolyl group having on the ring one substituent selected from the group consisting of substituent group D, each independently selected from the group consisting of: (d40) a triazinyl group; (d41) a substituted triazinyl group having, on the ring, 1 to 2 substituents independently selected from substituent group D; (d42) Frill (C １ -C ６ ) alkyl group; (d43) Substituted furyl (C １ -C ６ ) alkyl group; (d44) Thienyl (C １ -C ６ ) alkyl group; (d45) Substituted thienyl (C １ -C ６ ) alkyl group; (d46) a quinolinyl group; (d47) a substituted quinolinyl group having, on the ring, 1 to 6 substituents independently selected from substituent group D; (d48) benzothiazolyl group; (d49) a substituted benzothiazolyl group having, on the ring, 1 to 4 substituents independently selected from substituent group D; (d50) Pyridyl (C １ -C ６ ) alkyl group; (d51) Substituted pyridyl (C １ -C ６ ) alkyl group; (d52) Pyrazinyl (C １ -C ６ ) alkyl group; (d53) Substituted pyrazinyl having 1 to 3 substituents independently selected from the substituent group D on the ring (C １ -C ６ ) alkyl group; (d54) naphthyl group; (d55) a substituted naphthyl group having, on the ring, 1 to 7 substituents independently selected from the substituent group D; (d56) tetrahydronaphthyl; or (d57) a substituted tetrahydronaphthyl group having, on the ring, 1 to 10 substituents independently selected from the substituent group D, Substituent group A is (e1) a halogen atom; (e2) a cyano group; (e4) a hydroxyl group; (e5) a carboxyl group; (e6) (C １ -C ６ ) alkyl group; (e9) (C １ -C ６ ) an alkoxy group; (e10) (C ３ -C ６ ) a cycloalkyl group; (e11) (C １ -C ６ ) an alkylthio group; (e12) (C １ -C ６ ) an alkylsulfinyl group; (e13) (C １ -C ６ ) an alkylsulfonyl group; (e14) Halo (C １ -C ６ ) alkyl group; (e17) Halo (C １ -C ６ ) an alkoxy group; (e18) Halo (C ３ -C ６ ) a cycloalkyl group; (e19) Halo (C １ -C ６ ) an alkylthio group; (e20) Halo (C １ -C ６ ) an alkylsulfinyl group; (e21) Halo (C １ -C ６ ) an alkylsulfonyl group; (e22) (C １ -C ６ ) an alkylcarbonylamino group; (e24) (C １ -C ６ ) an alkylsulfonylamino group; (e28) N-(C １ -C ６ ) an alkylcarboxamide group; (e30) oxadiazolyl group; (e31) halogen atom, cyano group, (C １ -C ６ ) alkyl group, (C １ -C ６ ) an alkoxy group, (C ３ -C ６ ) a cycloalkyl group, (C １ -C ６ ) an alkylthio group, (C １ -C ６ ) an alkylsulfinyl group, (C １ -C ６ ) alkylsulfonyl group, halo(C １ -C ６ ) alkyl group and halo(C １ -C ６ ) a substituted oxadiazolyl group having one substituent on the ring independently selected from the group consisting of an alkoxy group; (e32) (C １ -C ６ ) an alkoxycarbonyl group; (e33) A halogen atom, a phenyl group, or (C) formed by two adjacent substituents taken together １ -C ６ ) a methylenedioxy group optionally substituted by 1 or 2 substituents selected from the group consisting of alkyl groups; (e34) N-(C １ -C ６ ) an alkylaminosulfonyl group; (e35) N,N-di(C １ -C ６ ) an alkylaminosulfonyl group; (e36) R ６ - (R ７ -N=)O=S group (in the formula, R ６ (C １ -C ６ ) alkyl group, (C ３ -C ６ ) cycloalkyl group, halo(C １ -C ６ ) an alkyl group, or (C １ -C ６ ) Alkoxy (C １ -C ６ ) represents an alkyl group; R ７ is a hydrogen atom, a cyano group, (C １ -C ６ ) alkyl group, (C ３ -C ６ ) cycloalkyl group, halo(C １ -C ６ ) alkyl group, (C ２ -C ６ ) alkylcarbonyl group, or halo(C ２ -C ６ ) represents an alkylcarbonyl group; and (e37) halogen atom, cyano group, (C １ -C ６ ) alkyl group, (C １ -C ６ ) alkoxy group and (C １ -C ６ ) a substituted (C) alkylcarbonyl group having 1 to 3 substituents on the ring, each independently selected from the group consisting of ３ -C ６ ) a cycloalkyl group; Substituent group B is (f1) a cyano group; (f2) (C ３ -C ６ ) a cycloalkyl group; (f3) (C １ -C ６ ) an alkoxy group; (f4) (C １ -C ６ ) an alkylthio group; (f5) (C １ -C ６ ) an alkylsulfinyl group; (f6) (C １ -C ６ ) an alkylsulfonyl group; (f7) Halo (C ３ -C ６ ) a cycloalkyl group; (f8) Halo (C １ -C ６ ) an alkoxy group; (f9) Halo (C １ -C ６ ) an alkylthio group; (f10) Halo (C １ -C ６ ) an alkylsulfinyl group; and (f11) Halo (C １ -C ６ ) alkylsulfonyl groups, Substituent group C is (g1) a cyano group; (g2) (C １ -C ６ ) alkyl group; (g3) (C ３ -C ６ ) a cycloalkyl group; (g4) (C １ -C ６ ) an alkoxy group; (g5) (C １ -C ６ ) an alkylthio group; (g6) (C １ -C ６ ) an alkylsulfinyl group; (g7) (C １ -C ６ ) an alkylsulfonyl group; (g8) Halo (C ３ -C ６ ) a cycloalkyl group; (g9) Halo (C １ -C ６ ) an alkoxy group; (g10) Halo (C １ -C ６ ) an alkylthio group; (g11) Halo (C １ -C ６ ) an alkylsulfinyl group; (g12) Halo (C １ -C ６ ) an alkylsulfonyl group; (g13) Halo (C １ -C ６ ) alkyl group; (g15) (C ２ -C ６ ) alkynyl groups; and (g16) consisting of a phenyl group; Substituent group D is (h1) a halogen atom; (h2) a cyano group; (h3) hydroxyl group; (h4) a carboxyl group; (h5) (C １ -C ６ ) alkyl group; (h6) (C １ -C ６ ) an alkoxy group; (h7) (C ３ -C ６ ) a cycloalkyl group; (h8) (C １ -C ６ ) an alkylthio group; (h9) (C １ -C ６ ) an alkylsulfinyl group; (h10) (C １ -C ６ ) an alkylsulfonyl group; (h11) Halo (C １ -C ６ ) alkyl group; (h12) Halo (C １ -C ６ ) an alkoxy group; (h13) Halo (C ３ -C ６ ) a cycloalkyl group; (h14) Halo (C １ -C ６ ) an alkylthio group; (h15) Halo (C １ -C ６ ) an alkylsulfinyl group; (h16) Halo (C １ -C ６ ) an alkylsulfonyl group; (h17) (C １ -C ６ ) an alkoxycarbonyl group; (h18) N-(C １ -C ６ ) an alkylcarboxamide group; (h20) A halogen atom, a phenyl group, and (C １ -C ６ ) a methylenedioxy group optionally substituted by 1 or 2 substituents selected from the group consisting of alkyl groups; (h21) nitro group; (h22) amino group; and (h23) The compound or salt thereof according to claim 1, which comprises a benzyloxycarbonyl group.

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

5. 5. An insecticide comprising the compound according to claim 1 or a salt or N-oxide thereof as an active ingredient.

6. 5. An agricultural and horticultural insecticide comprising the compound according to claim 1 or a salt or N-oxide thereof as an active ingredient.

7. 5. An animal ectoparasite-controlling agent comprising the compound according to claim 1 or a salt or N-oxide thereof as an active ingredient.

8. 5. An animal internal parasite control agent comprising the compound according to claim 1 or a salt or N-oxide thereof as an active ingredient.

9. 6. A method for using an insecticide comprising applying an effective amount of the insecticide according to claim 5 to plants or soil.

10. 5. Use of a compound according to any one of claims 1 to 4, or a salt or N-oxide thereof, as an insecticide, except for humans as the subject of use.

11. General formula (13A) 【Chemistry 2】 {During the ceremony, R １ teeth, (a1) a hydrogen atom; (a2) (C １ -C ６ ) alkyl group; (a3) (C ２ -C ６ ) alkenyl group; (a4) (C ２ -C ６ ) an alkynyl group; (a5) (C ３ -C ６ ) a cycloalkyl group; (a6) (C １ -C ６ ) an alkoxy group; (a7) Halo (C １ -C ６ ) alkyl group; (a8) (C １ -C ６ ) an alkylcarbonyl group; (a9) (C １ -C ６ ) an alkoxycarbonyl group; (a10) a cyano group, (C １ -C ６ ) an alkoxy group and (C ３ -C ６ ) a substituted cycloalkyl group having 1 to 3 substituents on the chain independently selected from the group consisting of cycloalkyl groups (C １ -C ６ ) alkyl group; (a11) a thiazolylmethyl group; (a12) a halogen atom, (C １ -C ６ ) alkyl group and (C １ -C ６ ) a substituted thiazolylmethyl group having, on the ring, 1 or 2 substituents independently selected from the group consisting of alkoxy groups; (a13) a benzyl group; or (a14) halogen atom, (C １ -C ６ ) alkyl group and (C １ -C ６ ) a substituted benzyl group having, on the ring, 1 to 3 substituents independently selected from the group consisting of alkoxy groups. R ２ teeth, (b1) an aryl group; (b2) a substituted aryl group having, on the ring, one or more substituents independently selected from the substituent group A; (b3) a 5- to 10-membered heterocyclic group; or (b4) represents a substituted 5- to 10-membered heterocyclic group having one or more substituents independently selected from the substituent group A on the ring. However, R ２ (C) is attached to the adjacent atom of the bond atom to the tetrahydropyridazine ring. １ -C ６ ) alkylsulfonyl group, halo(C １ -C ６ ) alkylsulfonyl group, N-(C １ -C ６ ) alkylaminosulfonyl group, N,N-di(C １ -C ６ ) an alkylaminosulfonyl group, and R ６ - (R ７ -N=)O=S group (in the formula, R ６ (C １ -C ６ ) alkyl group, (C ３ -C ６ ) cycloalkyl group, halo(C １ -C ６ ) an alkyl group, or (C １ -C ６ ) Alkoxy (C １ -C ６ ) represents an alkyl group; R ７ is a hydrogen atom, a cyano group, (C １ -C ６ ) alkyl group, (C ３ -C ６ ) cycloalkyl group, halo(C １ -C ６ ) alkyl group, (C ２ -C ６ ) alkylcarbonyl group, or halo(C ２ -C ６ ) denotes an alkylcarbonyl group. ) is unsubstituted. Substituent group A is (e1) a halogen atom; (e2) a cyano group; (e3) a nitro group; (e4) a hydroxyl group; (e5) a carboxyl group; (e6) (C １ -C ６ ) alkyl group; (e7) (C ２ -C ６ ) alkenyl group; (e8) (C ２ -C ６ ) an alkynyl group; (e9) (C １ -C ６ ) an alkoxy group; (e10) (C ３ -C ６ ) a cycloalkyl group; (e11) (C １ -C ６ ) an alkylthio group; (e12) (C １ -C ６ ) an alkylsulfinyl group; (e13) (C １ -C ６ ) an alkylsulfonyl group; (e14) Halo (C １ -C ６ ) alkyl group; (e15) Halo (C ２ -C ６ ) alkenyl group; (e16) Halo (C ２ -C ６ ) an alkynyl group; (e17) Halo (C １ -C ６ ) an alkoxy group; (e18) Halo (C ３ -C ６ ) a cycloalkyl group; (e19) Halo (C １ -C ６ ) an alkylthio group; (e20) Halo (C １ -C ６ ) an alkylsulfinyl group; (e21) Halo (C １ -C ６ ) an alkylsulfonyl group; (e22) (C １ -C ６ ) an alkylcarbonylamino group; (e23) Halo (C １ -C ６ ) an alkylcarbonylamino group; (e24) (C １ -C ６ ) an alkylsulfonylamino group; (e25) Halo (C １ -C ６ ) an alkylsulfonylamino group; (e26) SF ５ base; (e27) (C １ -C ６ ) Alkoxy (C １ -C ６ ) alkyl group; (e28) N-(C １ -C ６ ) an alkylcarboxamide group; (e29) N-halo (C １ -C ６ ) an alkylcarboxamide group; (e30) oxadiazolyl group; (e31) halogen atom, cyano group, (C １ -C ６ ) alkyl group, (C １ -C ６ ) an alkoxy group, (C ３ -C ６ ) a cycloalkyl group, (C １ -C ６ ) an alkylthio group, (C １ -C ６ ) an alkylsulfinyl group, (C １ -C ６ ) alkylsulfonyl group, halo(C １ -C ６ ) alkyl group and halo(C １ -C ６ ) a substituted oxadiazolyl group having one substituent on the ring independently selected from the group consisting of an alkoxy group; (e32) (C １ -C ６ ) an alkoxycarbonyl group; (e33) A halogen atom, a phenyl group, or a (C) group formed by two adjacent substituents taken together １ -C ６ ) a methylenedioxy group optionally substituted by 1 or 2 substituents selected from the group consisting of alkyl groups; (e34) N-(C １ -C ６ ) an alkylaminosulfonyl group; (e35) N,N-di(C １ -C ６ ) Alkylaminosulfonyl group (e36) R ６ - (R ７ -N=)O=S group (in the formula, R ６ (C １ -C ６ ) alkyl group, (C ３ -C ６ ) cycloalkyl group, halo(C １ -C ６ ) an alkyl group, or (C １ -C ６ ) Alkoxy (C １ -C ６ ) represents an alkyl group; R ７ is a hydrogen atom, a cyano group, (C １ -C ６ ) alkyl group, (C ３ -C ６ ) cycloalkyl group, halo(C １ -C ６ ) alkyl group, (C ２ -C ６ ) alkylcarbonyl group, or halo(C ２ -C ６ ) represents an alkylcarbonyl group; and (e37) halogen atom, cyano group, (C １ -C ６ ) alkyl group, (C １ -C ６ ) an alkoxy group and (C １ -C ６ ) a substituted (C) alkylcarbonyl group having 1 to 3 substituents on the ring, each independently selected from the group consisting of ３ -C ６ ) a cycloalkyl group.} or a salt thereof.

12. R １ and the substituent group A is the same as in claim 11, R ２ but, (b5) a phenyl group; (b6) a substituted phenyl group having, on the ring, 1 to 5 substituents independently selected from the substituent group A; (b7) a pyridyl group; (b8) a substituted pyridyl group having, on the ring, 1 to 4 substituents independently selected from the substituent group A; (b9) a pyridazinyl group; (b10) a substituted pyridazinyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b11) a pyrimidinyl group; (b12) a substituted pyrimidinyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b13) a pyrazinyl group; (b14) a substituted pyrazinyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b15) a furyl group; (b16) a substituted furyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b17) a thienyl group; (b18) a substituted thienyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b19) an isoxazolyl group; (b20) a substituted isoxazolyl group having, on the ring, 1 to 2 substituents independently selected from the substituent group A; (b21) an oxazolyl group; (b22) a substituted oxazolyl group having, on the ring, 1 to 2 substituents independently selected from the substituent group A; (b23) a pyrazolyl group; (b24) a substituted pyrazolyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b25) an imidazolyl group; (b26) a substituted imidazolyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b27) a triazolyl group; (b28) a substituted triazolyl group having, on the ring, 1 to 2 substituents independently selected from the substituent group A; (b29) a thiazolyl group; (b30) a substituted thiazolyl group having, on the ring, 1 to 2 substituents independently selected from the substituent group A; (b31) an isothiazolyl group; (b32) a substituted isothiazolyl group having, on the ring, 1 to 2 substituents independently selected from the substituent group A; (b33) a thiadiazolyl group; (b34) a substituted thiadiazolyl group having, on the ring, one substituent independently selected from the substituent group A; (b35) an imidazopyridyl group; (b36) a substituted imidazopyridyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b37) a quinoxalinyl group; (b38) a substituted quinoxalinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b39) a benzoxazolyl group; (b40) a substituted benzoxazolyl group having, on the ring, 1 to 4 substituents independently selected from the substituent group A; (b41) a benzimidazolyl group; (b42) a substituted benzimidazolyl group having 1 to 5 substituents 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 quinolinyl group; (b48) a substituted quinolinyl group having 1 to 6 substituents independently selected from the substituent group A on the ring; (b49) naphthyl group; (b50) a substituted naphthyl group having 1 to 7 substituents independently selected from the substituent group A on the ring; (b51) a triazinyl group; (b52) a substituted triazinyl group having 1 to 2 substituents independently selected from the substituent group A on the ring; (b53) a pyrrolyl group; (b54) a substituted pyrrolyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b55) a tetrazolyl group; (b56) a substituted tetrazolyl group having one substituent independently selected from the substituent group A on the ring; (b57) an oxadiazonyl group; (b58) a substituted oxadiazonyl group having one substituent independently selected from the substituent group A on the ring; (b59) 2-oxopyridyl group; (b60) a substituted 2-oxopyridyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b61) a benzofuranyl group; (b62) a substituted benzofuranyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b63) a benzoisoxazolyl group; (b64) a substituted benzoisoxazolyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b65) a benzothienyl group; (b66) a substituted benzothienyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b67) a benzoisothiazolyl group; (b68) a substituted benzisothiazolyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b69) an indolyl group; (b70) a substituted indolyl group having 1 to 6 substituents independently selected from the substituent group A on the ring; (b71) an isoindolyl group; (b72) a substituted isoindolyl group having 1 to 6 substituents independently selected from the substituent group A on the ring; (b73) indazolyl group; (b74) a substituted indazolyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b75) a benzotriazolyl group; (b76) a substituted benzotriazolyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b77) a furopyridyl group; (b78) a substituted furopyridyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b79) a thienopyridyl group; (b80) a substituted thienopyridyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b81) an indolizinyl group; (b82) a substituted indolizinyl group having 1 to 6 substituents independently selected from the substituent group A on the ring; (b83) a pyrrolopyridyl group; (b84) a substituted pyrrolopyridyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b85) a pyrrolopyrimidinyl group; (b86) a substituted pyrrolopyrimidinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b87) an oxazolopyridyl group; (b88) a substituted oxazolopyridyl group having 1 to 3 substituents independently selected from the substituent group A on the ring; (b89) an isoxazolopyridyl group; (b90) a substituted isoxazolopyridyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b91) an isothiazolopyridyl group; (b92) a substituted isothiazolopyridyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b93) an imidazopyrimidinyl group; (b94) a substituted imidazopyrimidinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b95) a pyrazolopyridyl group; (b96) a substituted pyrazolopyridyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b97) a pyrazolopyrimidinyl group; (b98) a substituted pyrazolopyrimidinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b99) a triazolopyridyl group; (b100) a substituted triazolopyridyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b101) a triazolopyrimidinyl group; (b102) a substituted triazolopyrimidinyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b103) an isoquinolinyl group; (b104) a substituted isoquinolinyl group having 1 to 6 substituents independently selected from the substituent group A on the ring; (b105) a cinnolinyl group; (b106) a substituted cinnolinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b107) a phthalazinyl group; (b108) a substituted phthalazinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b109) a quinazolinyl group; (b110) a substituted quinazolinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b111) a naphthyridinyl group; or (b112) The compound according to claim 11, which is a substituted naphthyridinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring, or a salt thereof.

13. R １ but, (a1) a hydrogen atom; (a2) (C １ -C ６ ) alkyl group; or (a4) (C ２ -C ６ ) an alkynyl group; R ２ but, (b5) a phenyl group; (b6) a substituted phenyl group having, on the ring, 1 to 5 substituents independently selected from the substituent group A; (b7) a pyridyl group; (b8) a substituted pyridyl group having, on the ring, 1 to 4 substituents independently selected from the substituent group A; (b9) a pyridazinyl group; (b10) a substituted pyridazinyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b11) a pyrimidinyl group; (b12) a substituted pyrimidinyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b13) a pyrazinyl group; (b14) a substituted pyrazinyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b15) a furyl group; (b16) a substituted furyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b17) a thienyl group; (b18) a substituted thienyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b19) an isoxazolyl group; (b20) a substituted isoxazolyl group having, on the ring, 1 to 2 substituents independently selected from the substituent group A; (b21) an oxazolyl group; (b22) a substituted oxazolyl group having, on the ring, 1 to 2 substituents independently selected from the substituent group A; (b23) a pyrazolyl group; (b24) a substituted pyrazolyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b25) an imidazolyl group; (b26) a substituted imidazolyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b27) a triazolyl group; (b28) a substituted triazolyl group having, on the ring, 1 to 2 substituents independently selected from the substituent group A; (b29) a thiazolyl group; (b30) a substituted thiazolyl group having, on the ring, 1 to 2 substituents independently selected from the substituent group A; (b31) an isothiazolyl group; (b32) a substituted isothiazolyl group having, on the ring, 1 to 2 substituents independently selected from the substituent group A; (b33) a thiadiazolyl group; (b34) a substituted thiadiazolyl group having, on the ring, one substituent independently selected from the substituent group A; (b35) an imidazopyridyl group; (b36) a substituted imidazopyridyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b37) a quinoxalinyl group; (b38) a substituted quinoxalinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b39) a benzoxazolyl group; (b40) a substituted benzoxazolyl group having, on the ring, 1 to 4 substituents independently selected from the substituent group A; (b41) a benzimidazolyl group; (b42) a substituted benzimidazolyl group having 1 to 5 substituents 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 quinolinyl group; or (b48) a substituted quinolinyl group having 1 to 6 substituents independently selected from the substituent group A on the ring, Substituent group A is (e1) a halogen atom; (e2) a cyano group; (e4) a hydroxyl group; (e5) a carboxyl group; (e6) (C １ -C ６ ) alkyl group; (e9) (C １ -C ６ ) an alkoxy group; (e10) (C ３ -C ６ ) a cycloalkyl group; (e11) (C １ -C ６ ) an alkylthio group; (e12) (C １ -C ６ ) an alkylsulfinyl group; (e13) (C １ -C ６ ) an alkylsulfonyl group; (e14) Halo (C １ -C ６ ) alkyl group; (e17) Halo (C １ -C ６ ) an alkoxy group; (e18) Halo (C ３ -C ６ ) a cycloalkyl group; (e19) Halo (C １ -C ６ ) an alkylthio group; (e20) Halo (C １ -C ６ ) an alkylsulfinyl group; (e21) Halo (C １ -C ６ ) an alkylsulfonyl group; (e22) (C １ -C ６ ) an alkylcarbonylamino group; (e24) (C １ -C ６ ) an alkylsulfonylamino group; (e28) N-(C １ -C ６ ) an alkylcarboxamide group; (e30) oxadiazolyl group; (e31) halogen atom, cyano group, (C １ -C ６ ) alkyl group, (C １ -C ６ ) an alkoxy group, (C ３ -C ６ ) a cycloalkyl group, (C １ -C ６ ) an alkylthio group, (C １ -C ６ ) an alkylsulfinyl group, (C １ -C ６ ) alkylsulfonyl group, halo(C １ -C ６ ) alkyl group and halo(C １ -C ６ ) a substituted oxadiazolyl group having one substituent on the ring independently selected from the group consisting of an alkoxy group; (e32) (C １ -C ６ ) an alkoxycarbonyl group; (e33) A halogen atom, a phenyl group, or a (C) group formed by two adjacent substituents taken together １ -C ６ ) a methylenedioxy group optionally substituted by 1 or 2 substituents selected from the group consisting of alkyl groups; (e34) N-(C １ -C ６ ) an alkylaminosulfonyl group; (e35) N,N-di(C １ -C ６ ) an alkylaminosulfonyl group; (e36) R ６ - (R ７ -N=)O=S group (in the formula, R ６ (C １ -C ６ ) alkyl group, (C ３ -C ６ ) cycloalkyl group, halo(C １ -C ６ ) an alkyl group, or (C １ -C ６ ) Alkoxy (C １ -C ６ ) represents an alkyl group; R ７ is a hydrogen atom, a cyano group, (C １ -C ６ ) alkyl group, (C ３ -C ６ ) cycloalkyl group, halo(C １ -C ６ ) alkyl group, (C ２ -C ６ ) alkylcarbonyl group, or halo(C ２ -C ６ ) represents an alkylcarbonyl group; and (e37) halogen atom, cyano group, (C １ -C ６ ) alkyl group, (C １ -C ６ ) an alkoxy group and (C １ -C ６ ) a substituted (C) alkylcarbonyl group having 1 to 3 substituents on the ring, each independently selected from the group consisting of ３ -C ６ 13. The compound or salt thereof according to claim 11 or 12, which comprises a cycloalkyl group.

14. R １ (a1) is a hydrogen atom; R 2 but, (b5) a phenyl group; (b6) a substituted phenyl group having, on the ring, 1 to 5 substituents independently selected from the substituent group A; (b7) a pyridyl group; (b8) a substituted pyridyl group having, on the ring, 1 to 4 substituents independently selected from the substituent group A; (b9) a pyridazinyl group; (b10) a substituted pyridazinyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b11) a pyrimidinyl group; (b12) a substituted pyrimidinyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b13) a pyrazinyl group; (b14) a substituted pyrazinyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b23) a pyrazolyl group; (b24) a substituted pyrazolyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b27) a triazolyl group; (b28) a substituted triazolyl group having, on the ring, 1 to 2 substituents independently selected from the substituent group A; (b29) a thiazolyl group; (b30) a substituted thiazolyl group having, on the ring, 1 to 2 substituents independently selected from the substituent group A; (b33) a thiadiazolyl group; (b34) a substituted thiadiazolyl group having, on the ring, one substituent independently selected from the substituent group A; (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 quinolinyl group; or (b48) a substituted quinolinyl group having 1 to 6 substituents independently selected from the substituent group A on the ring, Substituent group A is (e1) a halogen atom; (e2) a cyano group; (e6) (C １ -C ６ ) alkyl group; (e9) (C １ -C ６ ) an alkoxy group; (e11) (C １ -C ６ ) an alkylthio group; (e12) (C １ -C ６ ) an alkylsulfinyl group; (e13) (C １ -C ６ ) an alkylsulfonyl group; (e14) Halo (C １ -C ６ ) alkyl group; (e17) Halo (C １ -C ６ ) an alkoxy group; (e19) Halo (C １ -C ６ ) an alkylthio group; (e21) Halo (C １ -C ６ ) an alkylsulfonyl group; (e32) (C １ -C ６ ) an alkoxycarbonyl group; (e34) N-(C １ -C ６ ) alkylaminosulfonyl groups; and (e35) N,N-di(C １ -C ６ 13. The compound or salt thereof according to claim 11 or 12, which comprises an alkylaminosulfonyl group.

15. General formula (3A) 【Chemistry 3】 {During the ceremony, R １ teeth, (a1) a hydrogen atom; (a2) (C １ -C ６ ) alkyl group; (a3) (C ２ -C ６ ) alkenyl group; (a4) (C ２ -C ６ ) an alkynyl group; (a5) (C ３ -C ６ ) a cycloalkyl group; (a6) (C １ -C ６ ) an alkoxy group; (a7) Halo (C １ -C ６ ) alkyl group; (a8) (C １ -C ６ ) an alkylcarbonyl group; (a9) (C １ -C ６ ) an alkoxycarbonyl group; (a10) a cyano group, (C １ -C ６ ) an alkoxy group and (C ３ -C ６ ) a substituted cycloalkyl group having 1 to 3 substituents on the chain independently selected from the group consisting of cycloalkyl groups (C １ -C ６ ) alkyl group; (a11) a thiazolylmethyl group; (a12) a halogen atom, (C １ -C ６ ) alkyl group and (C １ -C ６ ) a substituted thiazolylmethyl group having, on the ring, 1 or 2 substituents independently selected from the group consisting of alkoxy groups; (a13) a benzyl group; or (a14) halogen atom, (C １ -C ６ ) alkyl group and (C １ -C ６ ) a substituted benzyl group having, on the ring, 1 to 3 substituents independently selected from the group consisting of alkoxy groups. R ２ teeth, (b1) an aryl group; (b2) a substituted aryl group having, on the ring, one or more substituents independently selected from the substituent group A; (b3) a 5- to 10-membered heterocyclic group; or (b4) represents a substituted 5- to 10-membered heterocyclic group having one or more substituents independently selected from the substituent group A on the ring. However, R ２ (C) is attached to the adjacent atom of the bond atom to the tetrahydropyridazine ring. １ -C ６ ) alkylsulfonyl group, halo(C １ -C ６ ) alkylsulfonyl group, N-(C １ -C ６ ) alkylaminosulfonyl group, N,N-di(C １ -C ６ ) an alkylaminosulfonyl group, and R ６ - (R ７ -N=)O=S group (in the formula, R ６ (C １ -C ６ ) alkyl group, (C ３ -C ６ ) cycloalkyl group, halo(C １ -C ６ ) an alkyl group, or (C １ -C ６ ) Alkoxy (C １ -C ６ ) represents an alkyl group; R ７ is a hydrogen atom, a cyano group, (C １ -C ６ ) alkyl group, (C ３ -C ６ ) cycloalkyl group, halo(C １ -C ６ ) alkyl group, (C ２ -C ６ ) alkylcarbonyl group, or halo(C ２ -C ６ ) denotes an alkylcarbonyl group. ) is unsubstituted. R ５ teeth, (i1) (C １ -C ６ ) alkyl group; or (i2) (C １ -C ６ ) Alkoxy (C １ -C ６ ) represents an alkyl group. Substituent group A is (e1) a halogen atom; (e2) a cyano group; (e3) a nitro group; (e4) a hydroxyl group; (e5) a carboxyl group; (e6) (C １ -C ６ ) alkyl group; (e7) (C ２ -C ６ ) alkenyl group; (e8) (C ２ -C ６ ) an alkynyl group; (e9) (C １ -C ６ ) an alkoxy group; (e10) (C ３ -C ６ ) a cycloalkyl group; (e11) (C １ -C ６ ) an alkylthio group; (e12) (C １ -C ６ ) an alkylsulfinyl group; (e13) (C １ -C ６ ) an alkylsulfonyl group; (e14) Halo (C １ -C ６ ) alkyl group; (e15) Halo (C ２ -C ６ ) alkenyl group; (e16) Halo (C ２ -C ６ ) an alkynyl group; (e17) Halo (C １ -C ６ ) an alkoxy group; (e18) Halo (C ３ -C ６ ) a cycloalkyl group; (e19) Halo (C １ -C ６ ) an alkylthio group; (e20) Halo (C １ -C ６ ) an alkylsulfinyl group; (e21) Halo (C １ -C ６ ) an alkylsulfonyl group; (e22) (C １ -C ６ ) an alkylcarbonylamino group; (e23) Halo (C １ -C ６ ) an alkylcarbonylamino group; (e24) (C １ -C ６ ) an alkylsulfonylamino group; (e25) Halo (C １ -C ６ ) an alkylsulfonylamino group; (e26) SF ５ base; (e27) (C １ -C ６ ) Alkoxy (C １ -C ６ ) alkyl group; (e28) N-(C １ -C ６ ) an alkylcarboxamide group; (e29) N-halo (C １ -C ６ ) an alkylcarboxamide group; (e30) oxadiazolyl group; (e31) halogen atom, cyano group, (C １ -C ６ ) alkyl group, (C １ -C ６ ) an alkoxy group, (C ３ -C ６ ) a cycloalkyl group, (C １ -C ６ ) an alkylthio group, (C １ -C ６ ) an alkylsulfinyl group, (C １ -C ６ ) alkylsulfonyl group, halo(C １ -C ６ ) alkyl group and halo(C １ -C ６ ) a substituted oxadiazolyl group having one substituent on the ring independently selected from the group consisting of an alkoxy group; (e32) (C １ -C ６ ) an alkoxycarbonyl group; (e33) A halogen atom, a phenyl group, or (C) formed by two adjacent substituents taken together １ -C ６ ) a methylenedioxy group optionally substituted by 1 or 2 substituents selected from the group consisting of alkyl groups; (e34) N-(C １ -C ６ ) an alkylaminosulfonyl group; (e35) N,N-di(C １ -C ６ ) Alkylaminosulfonyl group (e36) R ６ - (R ７ -N=)O=S group (in the formula, R ６ (C １ -C ６ ) alkyl group, (C ３ -C ６ ) cycloalkyl group, halo(C １ -C ６ ) an alkyl group, or (C １ -C ６ ) Alkoxy (C １ -C ６ ) represents an alkyl group; R ７ is a hydrogen atom, a cyano group, (C １ -C ６ ) alkyl group, (C ３ -C ６ ) cycloalkyl group, halo(C １ -C ６ ) alkyl group, (C ２ -C ６ ) alkylcarbonyl group, or halo(C ２ -C ６ ) represents an alkylcarbonyl group; and (e37) halogen atom, cyano group, (C １ -C ６ ) alkyl group, (C １ -C ６ ) alkoxy group and (C １ -C ６ ) a substituted (C) alkylcarbonyl group having 1 to 3 substituents on the ring, each independently selected from the group consisting of ３ -C ６ ) a cycloalkyl group.} or a salt thereof.

16. R １ , R ５ and the substituent group A is the same as in claim 15, R ２ but, (b5) a phenyl group; (b6) a substituted phenyl group having, on the ring, 1 to 5 substituents independently selected from the substituent group A; (b7) a pyridyl group; (b8) a substituted pyridyl group having, on the ring, 1 to 4 substituents independently selected from the substituent group A; (b9) a pyridazinyl group; (b10) a substituted pyridazinyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b11) a pyrimidinyl group; (b12) a substituted pyrimidinyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b13) a pyrazinyl group; (b14) a substituted pyrazinyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b15) a furyl group; (b16) a substituted furyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b17) a thienyl group; (b18) a substituted thienyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b19) an isoxazolyl group; (b20) a substituted isoxazolyl group having, on the ring, 1 to 2 substituents independently selected from the substituent group A; (b21) an oxazolyl group; (b22) a substituted oxazolyl group having, on the ring, 1 to 2 substituents independently selected from the substituent group A; (b23) a pyrazolyl group; (b24) a substituted pyrazolyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b25) an imidazolyl group; (b26) a substituted imidazolyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b27) a triazolyl group; (b28) a substituted triazolyl group having, on the ring, 1 to 2 substituents independently selected from the substituent group A; (b29) a thiazolyl group; (b30) a substituted thiazolyl group having, on the ring, 1 to 2 substituents independently selected from the substituent group A; (b31) an isothiazolyl group; (b32) a substituted isothiazolyl group having, on the ring, 1 to 2 substituents independently selected from the substituent group A; (b33) a thiadiazolyl group; (b34) a substituted thiadiazolyl group having, on the ring, one substituent independently selected from the substituent group A; (b35) an imidazopyridyl group; (b36) a substituted imidazopyridyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b37) a quinoxalinyl group; (b38) a substituted quinoxalinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b39) a benzoxazolyl group; (b40) a substituted benzoxazolyl group having, on the ring, 1 to 4 substituents independently selected from the substituent group A; (b41) a benzimidazolyl group; (b42) a substituted benzimidazolyl group having 1 to 5 substituents 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 thiazolopyridyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b47) a quinolinyl group; (b48) a substituted quinolinyl group having 1 to 6 substituents independently selected from the substituent group A on the ring; (b49) naphthyl group; (b50) a substituted naphthyl group having 1 to 7 substituents independently selected from the substituent group A on the ring; (b51) a triazinyl group; (b52) a substituted triazinyl group having 1 to 2 substituents independently selected from the substituent group A on the ring; (b53) a pyrrolyl group; (b54) a substituted pyrrolyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b55) a tetrazolyl group; (b56) a substituted tetrazolyl group having one substituent independently selected from the substituent group A on the ring; (b57) an oxadiazonyl group; (b58) a substituted oxadiazonyl group having one substituent independently selected from the substituent group A on the ring; (b59) 2-oxopyridyl group; (b60) a substituted 2-oxopyridyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b61) a benzofuranyl group; (b62) a substituted benzofuranyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b63) a benzoisoxazolyl group; (b64) a substituted benzoisoxazolyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b65) a benzothienyl group; (b66) a substituted benzothienyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b67) a benzoisothiazolyl group; (b68) a substituted benzisothiazolyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b69) an indolyl group; (b70) a substituted indolyl group having 1 to 6 substituents independently selected from the substituent group A on the ring; (b71) an isoindolyl group; (b72) a substituted isoindolyl group having 1 to 6 substituents independently selected from the substituent group A on the ring; (b73) indazolyl group; (b74) a substituted indazolyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b75) a benzotriazolyl group; (b76) a substituted benzotriazolyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b77) a furopyridyl group; (b78) a substituted furopyridyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b79) a thienopyridyl group; (b80) a substituted thienopyridyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b81) an indolizinyl group; (b82) a substituted indolizinyl group having 1 to 6 substituents independently selected from the substituent group A on the ring; (b83) a pyrrolopyridyl group; (b84) a substituted pyrrolopyridyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b85) a pyrrolopyrimidinyl group; (b86) a substituted pyrrolopyrimidinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b87) an oxazolopyridyl group; (b88) a substituted oxazolopyridyl group having 1 to 3 substituents independently selected from the substituent group A on the ring; (b89) an isoxazolopyridyl group; (b90) a substituted isoxazolopyridyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b91) an isothiazolopyridyl group; (b92) a substituted isothiazolopyridyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b93) an imidazopyrimidinyl group; (b94) a substituted imidazopyrimidinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b95) a pyrazolopyridyl group; (b96) a substituted pyrazolopyridyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b97) a pyrazolopyrimidinyl group; (b98) a substituted pyrazolopyrimidinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b99) a triazolopyridyl group; (b100) a substituted triazolopyridyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b101) a triazolopyrimidinyl group; (b102) a substituted triazolopyrimidinyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (b103) an isoquinolinyl group; (b104) a substituted isoquinolinyl group having 1 to 6 substituents independently selected from the substituent group A on the ring; (b105) a cinnolinyl group; (b106) a substituted cinnolinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b107) a phthalazinyl group; (b108) a substituted phthalazinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b109) a quinazolinyl group; (b110) a substituted quinazolinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b111) a naphthyridinyl group; or (b112) The compound according to claim 15, which is a substituted naphthyridinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring, or a salt thereof.

17. R １ but, (a1) a hydrogen atom; (a2) (C １ -C ６ ) alkyl group; or (a4) (C ２ -C ６ ) an alkynyl group; R ２ but, (b5) a phenyl group; (b6) a substituted phenyl group having, on the ring, 1 to 5 substituents independently selected from the substituent group A; (b7) a pyridyl group; (b8) a substituted pyridyl group having, on the ring, 1 to 4 substituents independently selected from the substituent group A; (b9) a pyridazinyl group; (b10) a substituted pyridazinyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b11) a pyrimidinyl group; (b12) a substituted pyrimidinyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b13) a pyrazinyl group; (b14) a substituted pyrazinyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b15) a furyl group; (b16) a substituted furyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b17) a thienyl group; (b18) a substituted thienyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b19) an isoxazolyl group; (b20) a substituted isoxazolyl group having, on the ring, 1 to 2 substituents independently selected from the substituent group A; (b21) an oxazolyl group; (b22) a substituted oxazolyl group having, on the ring, 1 to 2 substituents independently selected from the substituent group A; (b23) a pyrazolyl group; (b24) a substituted pyrazolyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b25) an imidazolyl group; (b26) a substituted imidazolyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b27) a triazolyl group; (b28) a substituted triazolyl group having, on the ring, 1 to 2 substituents independently selected from the substituent group A; (b29) a thiazolyl group; (b30) a substituted thiazolyl group having, on the ring, 1 to 2 substituents independently selected from the substituent group A; (b31) an isothiazolyl group; (b32) a substituted isothiazolyl group having, on the ring, 1 to 2 substituents independently selected from the substituent group A; (b33) a thiadiazolyl group; (b34) a substituted thiadiazolyl group having, on the ring, one substituent independently selected from the substituent group A; (b35) an imidazopyridyl group; (b36) a substituted imidazopyridyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b37) a quinoxalinyl group; (b38) a substituted quinoxalinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (b39) a benzoxazolyl group; (b40) a substituted benzoxazolyl group having, on the ring, 1 to 4 substituents independently selected from the substituent group A; (b41) a benzimidazolyl group; (b42) a substituted benzimidazolyl group having 1 to 5 substituents 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 quinolinyl group; or (b48) a substituted quinolinyl group having 1 to 6 substituents independently selected from the substituent group A on the ring, R ５ but, (i1) (C １ -C ６ ) alkyl group; or (i2) (C １ -C ６ ) Alkoxy (C １ -C ６ ) alkyl group, Substituent group A is (e1) a halogen atom; (e2) a cyano group; (e4) a hydroxyl group; (e5) a carboxyl group; (e6) (C １ -C ６ ) alkyl group; (e9) (C １ -C ６ ) an alkoxy group; (e10) (C ３ -C ６ ) a cycloalkyl group; (e11) (C １ -C ６ ) an alkylthio group; (e12) (C １ -C ６ ) an alkylsulfinyl group; (e13) (C １ -C ６ ) an alkylsulfonyl group; (e14) Halo (C １ -C ６ ) alkyl group; (e17) Halo (C １ -C ６ ) an alkoxy group; (e18) Halo (C ３ -C ６ ) a cycloalkyl group; (e19) Halo (C １ -C ６ ) an alkylthio group; (e20) Halo (C １ -C ６ ) an alkylsulfinyl group; (e21) Halo (C １ -C ６ ) an alkylsulfonyl group; (e22) (C １ -C ６ ) an alkylcarbonylamino group; (e24) (C １ -C ６ ) an alkylsulfonylamino group; (e28) N-(C １ -C ６ ) an alkylcarboxamide group; (e30) oxadiazolyl group; (e31) halogen atom, cyano group, (C １ -C ６ ) alkyl group, (C １ -C ６ ) an alkoxy group, (C ３ -C ６ ) a cycloalkyl group, (C １ -C ６ ) an alkylthio group, (C １ -C ６ ) an alkylsulfinyl group, (C １ -C ６ ) alkylsulfonyl group, halo(C １ -C ６ ) alkyl group and halo(C １ -C ６ ) a substituted oxadiazolyl group having one substituent on the ring independently selected from the group consisting of an alkoxy group; (e32) (C １ -C ６ ) an alkoxycarbonyl group; (e33) A halogen atom, a phenyl group, or (C) formed by two adjacent substituents taken together １ -C ６ ) a methylenedioxy group optionally substituted by 1 or 2 substituents selected from the group consisting of alkyl groups; (e34) N-(C １ -C ６ ) an alkylaminosulfonyl group; (e35) N,N-di(C １ -C ６ ) an alkylaminosulfonyl group; (e36) R ６ - (R ７ -N=)O=S group (in the formula, R ６ (C １ -C ６ ) alkyl group, (C ３ -C ６ ) cycloalkyl group, halo(C １ -C ６ ) an alkyl group, or (C １ -C ６ ) Alkoxy (C １ -C ６ ) represents an alkyl group; R ７ is a hydrogen atom, a cyano group, (C １ -C ６ ) alkyl group, (C ３ -C ６ ) cycloalkyl group, halo(C １ -C ６ ) alkyl group, (C ２ -C ６ ) alkylcarbonyl group, or halo(C ２ -C ６ ) represents an alkylcarbonyl group; and (e37) halogen atom, cyano group, (C １ -C ６ ) alkyl group, (C １ -C ６ ) alkoxy group and (C １ -C ６ ) a substituted (C) alkylcarbonyl group having 1 to 3 substituents on the ring, each independently selected from the group consisting of ３ -C ６ ) A cycloalkyl group, or a salt thereof, according to claim 15 or 16.

18. R １ (a1) is a hydrogen atom; R 2 but, (b5) a phenyl group; (b6) a substituted phenyl group having, on the ring, 1 to 5 substituents independently selected from the substituent group A; (b7) a pyridyl group; (b8) a substituted pyridyl group having, on the ring, 1 to 4 substituents independently selected from the substituent group A; (b9) a pyridazinyl group; (b10) a substituted pyridazinyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b11) a pyrimidinyl group; (b12) a substituted pyrimidinyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b13) a pyrazinyl group; (b14) a substituted pyrazinyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b23) a pyrazolyl group; (b24) a substituted pyrazolyl group having, on the ring, 1 to 3 substituents independently selected from the substituent group A; (b27) a triazolyl group; (b28) a substituted triazolyl group having, on the ring, 1 to 2 substituents independently selected from the substituent group A; (b29) a thiazolyl group; (b30) a substituted thiazolyl group having, on the ring, 1 to 2 substituents independently selected from the substituent group A; (b33) a thiadiazolyl group; (b34) a substituted thiadiazolyl group having, on the ring, one substituent independently selected from the substituent group A; (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 quinolinyl group; or (b48) a substituted quinolinyl group having 1 to 6 substituents independently selected from the substituent group A on the ring, R ５ But (i1) (C １ -C ６ ) alkyl group, Substituent group A is (e1) a halogen atom; (e2) a cyano group; (e6) (C １ -C ６ ) alkyl group; (e9) (C １ -C ６ ) an alkoxy group; (e11) (C １ -C ６ ) an alkylthio group; (e12) (C １ -C ６ ) an alkylsulfinyl group; (e13) (C １ -C ６ ) an alkylsulfonyl group; (e14) Halo (C １ -C ６ ) alkyl group; (e17) Halo (C １ -C ６ ) an alkoxy group; (e19) Halo (C １ -C ６ ) an alkylthio group; (e21) Halo (C １ -C ６ ) an alkylsulfonyl group; (e32) (C １ -C ６ ) an alkoxycarbonyl group; (e34) N-(C １ -C ６ ) alkylaminosulfonyl groups; and (e35) N,N-di(C １ -C ６ 17. The compound or salt thereof according to claim 15 or 16, which comprises an alkylaminosulfonyl group.

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