Mesionic arylpyridinium derivatives or salts thereof, pesticides containing the compounds, and methods for using the same

Abstract

In the production of crops in agriculture, horticulture, etc., damages caused by pest insects, etc. are still significant, and it has been required to develop a novel agricultural and horticultural insecticide due to factors such as the emergence of pest insects resistant to conventional chemicals.　The present inventors found that a compound represented by general formula (1) [wherein: Y represents an oxygen atom or a sulfur atom; Z represents an oxygen atom, a sulfur atom, etc.; R1 and R2 represent a substituted phenyl group, etc.; and R3 represents a hydrogen atom, etc.] or a salt thereof exhibits a high insecticidal effect on pest insects, etc. in the field of agriculture and horticulture. Thus, the present invention provides an agricultural and horticultural insecticide comprising the compound or a salt thereof as an active ingredient and a method for using the same.

Description

Technical Field

[0001] The present invention relates to a mesoionic arylpyridinium derivative or a salt thereof, an insecticide containing the compound, and a method for using the same.

Background Art

[0002] Patent Document 1 reports that certain tetrahydropyridazine-3,5-dione derivatives are useful as insecticides. However, there is no disclosure or suggestion regarding mesoionic compounds in such documents.

Prior Art Documents

Patent Documents

[0003]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0004] In crop production such as agriculture and horticulture, damage caused by pests and the like is still significant, and the development of new insecticides and acaricides is desired due to factors such as the emergence of resistant pests to existing drugs.

Means for Solving the Problems

[0005] As a result of intensive research to develop a new insecticide, particularly an insecticide for agriculture and horticulture, the present inventors have found that the compound represented by the general formula (1) of the present invention having a pyridinium structure exhibits excellent effects as an insecticide, and thus completed the present invention.

[0006] That is, the present invention provides [1] General formula (1)

Chemical formula

[0007] [2]R 2 , R 3 , Y, Z, substituent groups A, B, C and D are the same as in [1], R 1 is (a5) phenyl group; (a6) a substituted phenyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a7) pyridyl group; (a8) a substituted pyridyl group having 1 to 4 substituents independently selected from the group of substituents A on the ring; (a9) pyridazinyl group; (a10) a substituted pyridazinyl group having 1 to 3 substituents independently selected from the group of substituents A on the ring; (a11) pyrimidinyl group; (a12) a substituted pyrimidinyl group having 1 to 3 substituents independently selected from the group of substituents A on the ring; (a13) pyrazinyl group; (a14) a substituted pyrazinyl group having 1 to 3 substituents independently selected from the group of substituents A on the ring; (a15) triazinyl group; (a16) a substituted triazinyl group having 1 to 2 substituents independently selected from the group of substituents A on the ring; (a17) 2-oxopyridyl group; (a18) a substituted 2-oxopyridyl group having 1 to 4 substituents independently selected from the group of substituents A on the ring; (a19) furanyl group; (a20) a substituted furanyl group having 1 to 3 substituents independently selected from the group of substituents A on the ring; (a21) oxazolyl group; (a22) a substituted oxazolyl group having 1 to 2 substituents independently selected from the group of substituents A on the ring; (a23) isoxazolyl group; (a24) a substituted isoxazolyl group having 1 to 2 substituents independently selected from the group of substituents A on the ring; (a25) oxadiazinyl group; (a26) a substituted oxadiazinyl group having 1 substituent independently selected from the group of substituents A on the ring; (a27) thienyl group; (a28) a substituted thienyl group having 1 to 3 substituents independently selected from the group of substituents A on the ring; (a29) thiazolyl group; (a30) a substituted thiazolyl group having 1 to 2 substituents independently selected from the group of substituents A on the ring; (a31) isothiazolyl group; (a32) a substituted isothiazolyl group having 1 to 2 substituents independently selected from the group of substituents A on the ring; (a33) thiadiazolyl group; (a34) a substituted thiadiazolyl group having 1 substituent independently selected from the group of substituents A on the ring; (a35) pyrrolyl group;(a36) A substituted pyrrolyl group having from 1 to 4 substituents independently selected from the group of substituents A on the ring; (a37) A pyrazolyl group; (a38) A substituted pyrazolyl group having from 1 to 3 substituents independently selected from the group of substituents A on the ring; (a39) An imidazolyl group; (a40) A substituted imidazolyl group having from 1 to 3 substituents independently selected from the group of substituents A on the ring; (a41) A triazolyl group; (a42) A substituted triazolyl group having from 1 to 2 substituents independently selected from the group of substituents A on the ring; (a43) A tetrazolyl group; (a44) A substituted tetrazolyl group having 1 substituent independently selected from the group of substituents A on the ring; (a45) A benzofuranyl group; (a46) A substituted benzofuranyl group having from 1 to 5 substituents independently selected from the group of substituents A on the ring; (a47) A benzoxazolyl group; (a48) A substituted benzoxazolyl group having from 1 to 4 substituents independently selected from the group of substituents A on the ring; (a49) A benzisoxazolyl group; (a50) A substituted benzisoxazolyl group having from 1 to 4 substituents independently selected from the group of substituents A on the ring; (a51) A benzothienyl group; (a52) A substituted benzothienyl group having from 1 to 5 substituents independently selected from the group of substituents A on the ring; (a53) A benzothiazolyl group; (a54) A substituted benzothiazolyl group having from 1 to 4 substituents independently selected from the group of substituents A on the ring; (a55) A benzisothiazolyl group; (a56) A substituted benzisothiazolyl group having from 1 to 4 substituents independently selected from the group of substituents A on the ring; (a57) An indolyl group; (a58) A substituted indolyl group having from 1 to 6 substituents independently selected from the group of substituents A on the ring; (a59) An isoindolyl group; (a60) A substituted isoindolyl group having from 1 to 6 substituents independently selected from the group of substituents A on the ring; (a61) An indazolyl group; (a62) A substituted indazolyl group having from 1 to 5 substituents independently selected from the group of substituents A on the ring; (a63) A benzimidazolyl group; (a64) A substituted benzimidazolyl group having from 1 to 5 substituents independently selected from the group of substituents A on the ring;(a65) a benzotriazolyl group; (a66) a substituted benzotriazolyl group having 1 to 4 substituents each independently selected from the substituent group A on the ring; (a67) a furopyridyl group; (a68) a substituted furopyridyl group having 1 to 4 substituents each independently selected from the substituent group A on the ring; (a69) a thienopyridyl group; (a70) a substituted thienopyridyl group having 1 to 4 substituents each independently selected from the substituent group A on the ring; (a71) a thiazolopyridyl group; (a72) a substituted thiazolopyridyl group having 1 to 4 substituents each independently selected from the substituent group A on the ring; (a73) an imidazopyridyl group; (a74) a substituted imidazopyridyl group having 1 to 5 substituents each independently selected from the substituent group A on the ring; (a75) an indolizinyl group; (a76) a substituted indolizinyl group having 1 to 6 substituents each independently selected from the substituent group A on the ring; (a77) a pyrrolopyridyl group; (a78) a substituted pyrrolopyridyl group having 1 to 5 substituents each independently selected from the substituent group A on the ring; (a79) a pyrrolopyrimidinyl group; (a80) a substituted pyrrolopyrimidinyl group having 1 to 5 substituents each independently selected from the substituent group A on the ring; (a81) an oxazolopyridyl group; (a82) a substituted oxazolopyridyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (a83) an isoxazolopyridyl group; (a84) a substituted isoxazolopyridyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (a85) an isothiazolopyridyl group; (a86) a substituted isothiazolopyridyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (a87) an imidazopyrimidinyl group; (a88) a substituted imidazopyrimidinyl group having 1 to 5 substituents each independently selected from the substituent group A on the ring; (a89) a pyrazolopyridyl group; (a90) a substituted pyrazolopyridyl group having 1 to 5 substituents each independently selected from the substituent group A on the ring; (a91) a pyrazolopyrimidinyl group; (a92) a substituted pyrazolopyrimidinyl group having 1 to 5 substituents each independently selected from the substituent group A on the ring; (a93) a triazolopyridyl group;(a94) A substitution triazolopyridyl group having 1 to 4 substituents independently selected from the group of substituents A on the ring; (a95) A triazolopyrimidinyl group; (a96) A substituted triazolopyrimidinyl group having 1 to 4 substituents independently selected from the group of substituents A on the ring; (a97) A quinoxalinyl group; (a98) A substituted quinoxalinyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a99) A quinolinyl group; (a100) A substituted quinolinyl group having 1 to 6 substituents independently selected from the group of substituents A on the ring; (a101) A naphthyl group; (a102) A substituted naphthyl group having 1 to 7 substituents independently selected from the group of substituents A on the ring; (a103) An isoquinolinyl group; (a104) A substituted isoquinolinyl group having 1 to 6 substituents independently selected from the group of substituents A on the ring; (a105) A cinnolinyl group; (a106) A substituted cinnolinyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a107) A phthalazinyl group; (a108) A substituted phthalazinyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a109) A quinazolinyl group; (a110) A substituted quinazolinyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a111) A naphthyridinyl group; or (a112) A substituted naphthyridinyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring, the compound according to [1] and its salts;

[0008] [3]R 1 is (a5) phenyl group; (a6) a substituted phenyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a7) pyridyl group; (a8) a substituted pyridyl group having 1 to 4 substituents independently selected from the group of substituents A on the ring; (a9) pyridazinyl group; (a10) a substituted pyridazinyl group having 1 to 3 substituents independently selected from the group of substituents A on the ring; (a11) pyrimidinyl group; (a12) a substituted pyrimidinyl group having 1 to 3 substituents independently selected from the group of substituents A on the ring; (a13) pyrazinyl group; (a14) a substituted pyrazinyl group having 1 to 3 substituents independently selected from the group of substituents A on the ring; (a15) triazinyl group; (a16) a substituted triazinyl group having 1 to 2 substituents independently selected from the group of substituents A on the ring; (a17) 2-oxopyridyl group; (a18) a substituted 2-oxopyridyl group having 1 to 4 substituents independently selected from the group of substituents A on the ring; (a27) thienyl group; (a28) a substituted thienyl group having 1 to 3 substituents independently selected from the group of substituents A on the ring; (a97) quinoxalinyl group; (a98) a substituted quinoxalinyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a99) quinolinyl group; (a100) a substituted quinolinyl group having 1 to 6 substituents independently selected from the group of substituents A on the ring; (a101) naphthyl group; (a102) a substituted naphthyl group having 1 to 7 substituents independently selected from the group of substituents A on the ring; (a103) isoquinolinyl group; (a104) a substituted isoquinolinyl group having 1 to 6 substituents independently selected from the group of substituents A on the ring; (a105) cinnolinyl group; (a106) a substituted cinnolinyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a107) phthalazinyl group; (a108) a substituted phthalazinyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a109) quinazolinyl group; (a110) a substituted quinazolinyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a111) naphthyridinyl group;or a substituted naphthyridinyl group having on the ring from 1 to 5 substituents each independently selected from the substituent group A; R 2 is (b1) (C1-C6) alkyl group; (b2) (C2-C6) alkenyl group; (b3) (C2-C6) alkynyl group; (b4) (C3-C6) cycloalkyl group; (b5) halo(C1-C6) alkyl group; (b6) halo(C2-C6) alkenyl group; (b7) halo(C2-C6) alkynyl group; (b8) substituted (C1-C6) alkyl group having 1 to 3 substituents independently selected from substituent group B; (b9) substituted (C3-C6) cycloalkyl group having 1 to 3 substituents on the ring independently selected from substituent group C; (b14) piperidinyl group; (b15) morpholinyl group; (b16) phenyl group; (b17) substituted phenyl group having 1 to 5 substituents on the ring independently selected from substituent group D; (b18) pyridyl group; (b19) substituted pyridyl group having 1 to 4 substituents on the ring independently selected from substituent group D; (b20) pyridazinyl group; (b21) substituted pyridazinyl group having 1 to 3 substituents on the ring independently selected from substituent group D; (b22) pyrimidinyl group; (b23) substituted pyrimidinyl group having 1 to 3 substituents on the ring independently selected from substituent group D; (b24) pyrazinyl group; (b25) substituted pyrazinyl group having 1 to 3 substituents on the ring independently selected from substituent group D; (b26) triazinyl group; (b27) substituted triazinyl group having 1 to 2 substituents on the ring independently selected from substituent group D; (b28) furanyl group; (b29) substituted furanyl group having 1 to 3 substituents on the ring independently selected from substituent group D; (b30) oxazolyl group; (b31) substituted oxazolyl group having 1 to 2 substituents on the ring independently selected from substituent group D; (b32) isoxazolyl group; (b33) substituted isoxazolyl group having 1 to 2 substituents on the ring independently selected from substituent group D; (b34) thienyl group; (b35) substituted thienyl group having 1 to 3 substituents on the ring independently selected from substituent group D; (b36) thiazolyl group; (b37) substituted thiazolyl group having 1 to 2 substituents on the ring independently selected from substituent group D; (b38) isothiazolyl group;(b39) A substituted isothiazolyl group having 1 to 2 substituents independently selected from the group of substituents D on the ring; (b40) A thiadiazolyl group; (b41) A substituted thiadiazolyl group having 1 substituent independently selected from the group of substituents D on the ring; (b42) A pyrazolyl group; (b43) A substituted pyrazolyl group having 1 to 3 substituents independently selected from the group of substituents D on the ring; (b44) A triazolyl group; (b45) A substituted triazolyl group having 1 to 2 substituents independently selected from the group of substituents D on the ring; (b46) A tetrazolyl group; (b47) A substituted tetrazolyl group having 1 substituent independently selected from the group of substituents D on the ring; (b54) A naphthyl group; (b55) A substituted naphthyl group having 1 to 7 substituents independently selected from the group of substituents D on the ring; (b58) A phenyl(C1-C6)alkyl group; (b59) A substituted phenyl(C1-C6)alkyl group having 1 to 5 substituents independently selected from the group of substituents D on the ring; (b60) A pyridyl(C1-C6)alkyl group; (b61) A substituted pyridyl(C1-C6)alkyl group having 1 to 4 substituents independently selected from the group of substituents D on the ring; (b62) A pyrazinyl(C1-C6)alkyl group; (b63) A substituted pyrazinyl(C1-C6)alkyl group having 1 to 3 substituents independently selected from the group of substituents D on the ring; (b64) A pyrimidinyl(C1-C6)alkyl group; (b65) A substituted pyrimidinyl(C1-C6)alkyl group having 1 to 3 substituents independently selected from the group of substituents D on the ring; (b66) A furanyl(C1-C6)alkyl group; (b67) A substituted furanyl(C1-C6)alkyl group having 1 to 3 substituents independently selected from the group of substituents D on the ring; (b68) A thienyl(C1-C6)alkyl group; (b69) A substituted thienyl(C1-C6)alkyl group having 1 to 3 substituents independently selected from the group of substituents D on the ring; or (b70) An amino group,; R 3 is (c1) A hydrogen atom; (c2) A (C1-C6)alkyl group; or (c3) A (C3-C6)cycloalkyl group, R2 and R 3 may be joined to each other to form a ring, Y is an oxygen atom or a sulfur atom, Z is an oxygen atom, a sulfur atom, or NOR 4 group (wherein R 4 represents a hydrogen atom, a (C1-C6) alkyl group, or a halo (C1-C6) alkyl group.), the substituent group A is, (d1) halogen atom; (d2) cyano group; (d6) (C1-C6) alkyl group; (d7) (C2-C6) alkenyl group; (d8) (C2-C6) alkynyl group; (d9) (C1-C6) alkoxy group; (d10) (C3-C6) cycloalkyl group; (d11) (C1-C6) alkylthio group; (d12) (C1-C6) alkylsulfinyl group; (d13) (C1-C6) alkylsulfonyl group; (d14) halo(C1-C6) alkyl group; (d15) halo(C2-C6) alkenyl group; (d16) halo(C2-C6) alkynyl group; (d17) halo(C1-C6) alkoxy group; (d18) halo(C3-C6) cycloalkyl group; (d19) halo(C1-C6) alkylthio group; (d20) halo(C1-C6) alkylsulfinyl group; (d21) halo(C1-C6) alkylsulfonyl group; (d22) N,N-di(C1-C6) alkylaminosulfonyl group; (d23) substituted (C3-C6) cycloalkyl group having 1 to 3 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, and a (C1-C6) alkylcarbonyl group on the ring; (d26) (C1-C6) alkoxy(C1-C6) alkyl group; (d27) (C1-C6) alkoxy(C1-C6) alkoxy group; (d32) (C1-C6) alkoxycarbonyl group; (d33) methylenedioxy group optionally substituted with 1 to 2 substituents selected from the group consisting of a halogen atom, a phenyl group, and a (C1-C6) alkyl group, formed by two adjacent substituents A together; (d36) furanyl group; (d37) substituted furanyl group having 1 to 3 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group on the ring; (d38) oxazolyl group; (d39) substituted oxazolyl group having 1 to 2 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group on the ring; (d40) isoxazolyl group;(d41) A substituted isoxazolyl group having 1 to 2 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group on the ring; (d42) An oxadiazolyl group; (d43) A substituted oxadiazolyl group having 1 substituent independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group on the ring; (d52) A pyrrolyl group; (d53) A substituted pyrrolyl group having 1 to 3 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group on the ring; (d54) A pyrazolyl group; (d55) A substituted pyrazolyl group having 1 to 2 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group on the ring; (d56) An imidazolyl group; (d57) A substituted imidazolyl group having 1 to 2 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group on the ring; (d58) A triazolyl group; (d59) A substituted triazolyl group having 1 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 halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group on the ring; (d60) A tetrazolyl group; (d61) A substituted tetrazolyl group having 1 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 halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group on the ring; (d62) An oxazolinyl group;(d63) A substituted oxazolinyl group having 1 to 4 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group on the ring; (d64) A thiazolinyl group; (d65) A substituted thiazolinyl group having 1 to 4 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group on the ring; (d66) An isoxazolinyl group; (d67) A substituted isoxazolinyl group having 1 to 4 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group on the ring; (d68) An isothiazolinyl group; (d69) A substituted isothiazolinyl group having 1 to 4 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group on the ring; (d70) A pyrrolidinyl group; (d71) A substituted pyrrolidinyl group having 1 to 4 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group on the ring; (d72) An imidazolinyl group; (d73) A substituted imidazolinyl group having 1 to 4 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group on the ring; (d95) An aminosulfonyl group; and (d96) An N-(C1-C6) alkylaminosulfonyl group,; The substituent group B is, (e1) cyano group; (e2) (C3-C6) cycloalkyl group; (e3) (C1-C6) alkoxy group; (e4) (C1-C6) alkylthio group; (e5) (C1-C6) alkylsulfinyl group; (e6) (C1-C6) alkylsulfonyl group; (e7) halo(C3-C6) cycloalkyl group; (e8) halo(C1-C6) alkoxy group; (e9) halo(C1-C6) alkylthio group; (e10) halo(C1-C6) alkylsulfinyl group; (e11) halo(C1-C6) alkylsulfonyl group; and (e12) (C1-C6) alkoxycarbonyl group, Substituent group C is, (f1) cyano group; (f2) (C1-C6) alkyl group; and (f10) halo(C1-C6) alkyl group, Substituent group D is, (g1) halogen atom; (g2) cyano group; (g3) nitro group; (g7) (C1-C6) alkyl group; (g8) (C1-C6) alkoxy group; (g9) (C3-C6) cycloalkyl group; (g10) (C1-C6) alkylthio group; (g11) (C1-C6) alkylsulfinyl group; (g12) (C1-C6) alkylsulfonyl group; (g13) halo(C1-C6) alkyl group; (g14) halo(C1-C6) alkoxy group; (g15) halo(C3-C6) cycloalkyl group; (g16) halo(C1-C6) alkylthio group; (g17) halo(C1-C6) alkylsulfinyl group; (g18) halo(C1-C6) alkylsulfonyl group; (g23) phenyl group; (g24) substituted phenyl group having 1 to 5 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group on the ring; and (g25) methylenedioxy group optionally substituted with 1 to 2 substituents selected from the group consisting of a halogen atom, a phenyl group, and a (C1-C6) alkyl group formed by two adjacent substituents together, the compound according to [1] or [2] and salts thereof,

[0009] [4]R 1is (a5) a phenyl group; (a6) a substituted phenyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a7) a pyridyl group; (a8) a substituted pyridyl group having 1 to 4 substituents independently selected from the group of substituents A on the ring; (a13) a pyrazinyl group; (a14) a substituted pyrazinyl group having 1 to 3 substituents independently selected from the group of substituents A on the ring; (a99) a quinolinyl group; or (a100) a substituted quinolinyl group having 1 to 6 substituents independently selected from the group of substituents A on the ring, R 2 is (b1) a (C1-C6) alkyl group; (b4) a (C3-C6) cycloalkyl group; (b8) a substituted (C1-C6) alkyl group having 1 to 3 substituents independently selected from the group of substituents B; (b15) a morpholinyl group; (b16) a phenyl group; (b17) a substituted phenyl group having 1 to 5 substituents independently selected from the group of substituents D on the ring; (b18) a pyridyl group; (b19) a substituted pyridyl group having 1 to 4 substituents independently selected from the group of substituents D on the ring; (b22) a pyrimidinyl group; (b23) a substituted pyrimidinyl group having 1 to 3 substituents independently selected from the group of substituents D on the ring; (b32) an isoxazolyl group; (b33) a substituted isoxazolyl group having 1 to 2 substituents independently selected from the group of substituents D on the ring; (b42) a pyrazolyl group; or (b43) a substituted pyrazolyl group having 1 to 3 substituents independently selected from the group of substituents D on the ring, R 3 is a hydrogen atom, Y is an oxygen atom or a sulfur atom, Z is an oxygen atom, a sulfur atom, or a NOR 4 group (wherein R 4 represents a hydrogen atom.), The group of substituents A is (d1) A halogen atom; (d2) A cyano group; (d6) A (C1-C6) alkyl group; (d9) A (C1-C6) alkoxy group; (d10) A (C3-C6) cycloalkyl group; (d12) A (C1-C6) alkylsulfinyl group; (d13) A (C1-C6) alkylsulfonyl group; (d14) A halo(C1-C6)alkyl group; (d17) A halo(C1-C6)alkoxy group; (d43) 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 halo(C1-C6)alkyl group and a halo(C1-C6)alkoxy group; and (d95) An aminosulfonyl group, The substituent group B is (e3) A (C1-C6) alkoxy group; and (e4) A (C1-C6) alkylthio group, The substituent group D is (g1) A halogen atom; (g2) A cyano group; (g7) A (C1-C6) alkyl group; (g8) A (C1-C6) alkoxy group; (g10) A (C1-C6) alkylthio group; (g13) A halo(C1-C6)alkyl group; (g14) A halo(C1-C6)alkoxy group; (g16) A halo(C1-C6)alkylthio group; and (g24) A substituted phenyl group having on the ring from 1 to 5 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6)alkyl group and a halo(C1-C6)alkoxy group, the compound according to any one of [1] to [3] and salts thereof,

[0010] [5] An insecticide characterized by containing as an active ingredient the compound according to any one of [1] to [4] or a salt thereof, [6] An insecticide for agricultural and horticultural use characterized by containing as an active ingredient the compound according to any one of [1] to [4] or a salt thereof, [7] A method for using an insecticide, characterized by treating a plant or soil with an effective amount of the insecticide according to [5] or [6], Use of the compound according to any one of [8][1] to [4] or a salt thereof as an insecticide,

[0011] [9] General formula (2)

Chemical formula

[0012]

[10] R 7 and the substituent group A are the same as in [9], R 1 is (a5) phenyl group; (a6) a substituted phenyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (a7) pyridyl group; (a8) a substituted pyridyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (a9) pyridazinyl group; (a10) a substituted pyridazinyl group having 1 to 3 substituents independently selected from the substituent group A on the ring; (a11) pyrimidinyl group; (a12) a substituted pyrimidinyl group having 1 to 3 substituents independently selected from the substituent group A on the ring; (a13) pyrazinyl group; (a14) a substituted pyrazinyl group having 1 to 3 substituents independently selected from the substituent group A on the ring; (a15) triazinyl group; (a16) a substituted triazinyl group having 1 to 2 substituents independently selected from the substituent group A on the ring; (a17) 2-oxopyridyl group; (a18) a substituted 2-oxopyridyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (a19) furanyl group; (a20) a substituted furanyl group having 1 to 3 substituents independently selected from the substituent group A on the ring; (a21) oxazolyl group; (a22) a substituted oxazolyl group having 1 to 2 substituents independently selected from the substituent group A on the ring; (a23) isoxazolyl group; (a24) a substituted isoxazolyl group having 1 to 2 substituents independently selected from the substituent group A on the ring; (a25) oxadiazinyl group; (a26) a substituted oxadiazinyl group having 1 substituent independently selected from the substituent group A on the ring; (a27) thienyl group; (a28) a substituted thienyl group having 1 to 3 substituents independently selected from the substituent group A on the ring; (a29) thiazolyl group; (a30) a substituted thiazolyl group having 1 to 2 substituents independently selected from the substituent group A on the ring; (a31) isothiazolyl group; (a32) a substituted isothiazolyl group having 1 to 2 substituents independently selected from the substituent group A on the ring; (a33) thiadiazolyl group; (a34) a substituted thiadiazolyl group having 1 substituent independently selected from the substituent group A on the ring; (a35) pyrrolyl group;(a36) A substituted pyrrolyl group having from 1 to 4 substituents independently selected from the group of substituents A on the ring; (a37) A pyrazolyl group; (a38) A substituted pyrazolyl group having from 1 to 3 substituents independently selected from the group of substituents A on the ring; (a39) An imidazolyl group; (a40) A substituted imidazolyl group having from 1 to 3 substituents independently selected from the group of substituents A on the ring; (a41) A triazolyl group; (a42) A substituted triazolyl group having from 1 to 2 substituents independently selected from the group of substituents A on the ring; (a43) A tetrazolyl group; (a44) A substituted tetrazolyl group having 1 substituent independently selected from the group of substituents A on the ring; (a45) A benzofuranyl group; (a46) A substituted benzofuranyl group having from 1 to 5 substituents independently selected from the group of substituents A on the ring; (a47) A benzoxazolyl group; (a48) A substituted benzoxazolyl group having from 1 to 4 substituents independently selected from the group of substituents A on the ring; (a49) A benzisoxazolyl group; (a50) A substituted benzisoxazolyl group having from 1 to 4 substituents independently selected from the group of substituents A on the ring; (a51) A benzothienyl group; (a52) A substituted benzothienyl group having from 1 to 5 substituents independently selected from the group of substituents A on the ring; (a53) A benzothiazolyl group; (a54) A substituted benzothiazolyl group having from 1 to 4 substituents independently selected from the group of substituents A on the ring; (a55) A benzisothiazolyl group; (a56) A substituted benzisothiazolyl group having from 1 to 4 substituents independently selected from the group of substituents A on the ring; (a57) An indolyl group; (a58) A substituted indolyl group having from 1 to 6 substituents independently selected from the group of substituents A on the ring; (a59) An isoindolyl group; (a60) A substituted isoindolyl group having from 1 to 6 substituents independently selected from the group of substituents A on the ring; (a61) An indazolyl group; (a62) A substituted indazolyl group having from 1 to 5 substituents independently selected from the group of substituents A on the ring; (a63) A benzimidazolyl group; (a64) A substituted benzimidazolyl group having from 1 to 5 substituents independently selected from the group of substituents A on the ring;(a65) benzotriazolyl group; (a66) a substituted benzotriazolyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (a67) furopyridyl group; (a68) a substituted furopyridyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (a69) thienopyridyl group; (a70) a substituted thienopyridyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (a71) thiazolopyridyl group; (a72) a substituted thiazolopyridyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (a73) imidazopyridyl group; (a74) a substituted imidazopyridyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (a75) indolizinyl group; (a76) a substituted indolizinyl group having 1 to 6 substituents independently selected from the substituent group A on the ring; (a77) pyrrolopyridyl group; (a78) a substituted pyrrolopyridyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (a79) pyrrolopyrimidinyl group; (a80) a substituted pyrrolopyrimidinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (a81) oxazolopyridyl group; (a82) a substituted oxazolopyridyl group having 1 to 3 substituents independently selected from the substituent group A on the ring; (a83) isoxazolopyridyl group; (a84) a substituted isoxazolopyridyl group having 1 to 3 substituents independently selected from the substituent group A on the ring; (a85) isothiazolopyridyl group; (a86) a substituted isothiazolopyridyl group having 1 to 3 substituents independently selected from the substituent group A on the ring; (a87) imidazopyrimidinyl group; (a88) a substituted imidazopyrimidinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (a89) pyrazolopyridyl group; (a90) a substituted pyrazolopyridyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (a91) pyrazolopyrimidinyl group; (a92) a substituted pyrazolopyrimidinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (a93) triazolopyridyl group;(a94) A substitution triazolopyridyl group having 1 to 4 substituents independently selected from the group of substituents A on the ring; (a95) A triazolopyrimidinyl group; (a96) A substituted triazolopyrimidinyl group having 1 to 4 substituents independently selected from the group of substituents A on the ring; (a97) A quinoxalinyl group; (a98) A substituted quinoxalinyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a99) A quinolinyl group; (a100) A substituted quinolinyl group having 1 to 6 substituents independently selected from the group of substituents A on the ring; (a101) A naphthyl group; (a102) A substituted naphthyl group having 1 to 7 substituents independently selected from the group of substituents A on the ring; (a103) An isoquinolinyl group; (a104) A substituted isoquinolinyl group having 1 to 6 substituents independently selected from the group of substituents A on the ring; (a105) A cinnolinyl group; (a106) A substituted cinnolinyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a107) A phthalazinyl group; (a108) A substituted phthalazinyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a109) A quinazolinyl group; (a110) A substituted quinazolinyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a111) A naphthyridinyl group; or (a112) A substituted naphthyridinyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring, the compound according to [9] and salts thereof;

[0013]

[11] R 1 is (a5) phenyl group; (a6) a substituted phenyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a7) pyridyl group; (a8) a substituted pyridyl group having 1 to 4 substituents independently selected from the group of substituents A on the ring; (a9) pyridazinyl group; (a10) a substituted pyridazinyl group having 1 to 3 substituents independently selected from the group of substituents A on the ring; (a11) pyrimidinyl group; (a12) a substituted pyrimidinyl group having 1 to 3 substituents independently selected from the group of substituents A on the ring; (a13) pyrazinyl group; (a14) a substituted pyrazinyl group having 1 to 3 substituents independently selected from the group of substituents A on the ring; (a15) triazinyl group; (a16) a substituted triazinyl group having 1 to 2 substituents independently selected from the group of substituents A on the ring; (a17) 2-oxopyridyl group; (a18) a substituted 2-oxopyridyl group having 1 to 4 substituents independently selected from the group of substituents A on the ring; (a27) thienyl group; (a28) a substituted thienyl group having 1 to 3 substituents independently selected from the group of substituents A on the ring; (a97) quinoxalinyl group; (a98) a substituted quinoxalinyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a99) quinolinyl group; (a100) a substituted quinolinyl group having 1 to 6 substituents independently selected from the group of substituents A on the ring; (a101) naphthyl group; (a102) a substituted naphthyl group having 1 to 7 substituents independently selected from the group of substituents A on the ring; (a103) isoquinolinyl group; (a104) a substituted isoquinolinyl group having 1 to 6 substituents independently selected from the group of substituents A on the ring; (a105) cinnolinyl group; (a106) a substituted cinnolinyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a107) phthalazinyl group; (a108) a substituted phthalazinyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a109) quinazolinyl group; (a110) a substituted quinazolinyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a111) naphthyridinyl group;or a substituted naphthyridinyl group having from 1 to 5 substituents independently selected from the group A of substituents on the ring; R 7 is (h1) a (C1-C6) alkyl group; or (h2) a (C1-C6) alkoxy(C1-C6) alkyl group, the group A of substituents is (d1) halogen atom; (d2) cyano group; (d6) (C1-C6) alkyl group; (d7) (C2-C6) alkenyl group; (d8) (C2-C6) alkynyl group; (d9) (C1-C6) alkoxy group; (d10) (C3-C6) cycloalkyl group; (d11) (C1-C6) alkylthio group; (d12) (C1-C6) alkylsulfinyl group; (d13) (C1-C6) alkylsulfonyl group; (d14) halo(C1-C6) alkyl group; (d15) halo(C2-C6) alkenyl group; (d16) halo(C2-C6) alkynyl group; (d17) halo(C1-C6) alkoxy group; (d18) halo(C3-C6) cycloalkyl group; (d19) halo(C1-C6) alkylthio group; (d20) halo(C1-C6) alkylsulfinyl group; (d21) halo(C1-C6) alkylsulfonyl group; (d22) N,N-di(C1-C6) alkylaminosulfonyl group; (d23) substituted (C3-C6) cycloalkyl group having 1 to 3 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, and a (C1-C6) alkylcarbonyl group on the ring; (d26) (C1-C6) alkoxy(C1-C6) alkyl group; (d27) (C1-C6) alkoxy(C1-C6) alkoxy group; (d32) (C1-C6) alkoxycarbonyl group; (d33) methylenedioxy group optionally substituted with 1 to 2 substituents selected from the group consisting of a halogen atom, a phenyl group, and a (C1-C6) alkyl group, formed by two adjacent substituents A together; (d36) furanyl group; (d37) substituted furanyl group having 1 to 3 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group on the ring; (d38) oxazolyl group; (d39) substituted oxazolyl group having 1 to 2 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group on the ring; (d40) isoxazolyl group;(d41) A substituted isoxazolyl group having 1 to 2 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group on the ring; (d42) An oxadiazolyl group; (d43) A substituted oxadiazolyl group having 1 substituent independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group on the ring; (d52) A pyrrolyl group; (d53) A substituted pyrrolyl group having 1 to 3 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group on the ring; (d54) A pyrazolyl group; (d55) A substituted pyrazolyl group having 1 to 2 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group on the ring; (d56) An imidazolyl group; (d57) A substituted imidazolyl group having 1 to 2 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group on the ring; (d58) A triazolyl group; (d59) A substituted triazolyl group having 1 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 halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group on the ring; (d60) A tetrazolyl group; (d61) A substituted tetrazolyl group having 1 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 halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group on the ring; (d62) An oxazolinyl group;(d63) A substituted oxazolinyl group having 1 to 4 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group on the ring; (d64) A thiazolinyl group; (d65) A substituted thiazolinyl group having 1 to 4 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group on the ring; (d66) An isoxazolinyl group; (d67) A substituted isoxazolinyl group having 1 to 4 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group on the ring; (d68) An isothiazolinyl group; (d69) A substituted isothiazolinyl group having 1 to 4 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group on the ring; (d70) A pyrrolidinyl group; (d71) A substituted pyrrolidinyl group having 1 to 4 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group on the ring; (d72) An imidazolinyl group; (d73) A substituted imidazolinyl group having 1 to 4 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group on the ring; (d95) An aminosulfonyl group; and (d96) An N-(C1-C6) alkylaminosulfonyl group, the compound according to [9] or

[10] and salts thereof;

[0014]

[12] R 1 is (a5) phenyl group; (a6) a substituted phenyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a7) pyridyl group; (a8) a substituted pyridyl group having 1 to 4 substituents independently selected from the group of substituents A on the ring; (a13) pyrazinyl group; (a14) a substituted pyrazinyl group having 1 to 3 substituents independently selected from the group of substituents A on the ring; (a99) quinolinyl group; or (a100) a substituted quinolinyl group having 1 to 6 substituents independently selected from the group of substituents A on the ring, R 7 is a (h1) (C1-C6) alkyl group, The group of substituents A is (d1) halogen atom; (d2) cyano group; (d6) (C1-C6) alkyl group; (d9) (C1-C6) alkoxy group; (d10) (C3-C6) cycloalkyl group; (d11) (C1-C6) alkylthio group; (d12) (C1-C6) alkylsulfinyl group; (d13) (C1-C6) alkylsulfonyl group; (d14) halo(C1-C6) alkyl group; (d17) halo(C1-C6) alkoxy group; (d43) a substituted oxadiazolyl group having 1 substituent independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group on the ring; (d61) a substituted tetrazolyl group having 1 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 halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group on the ring; and (d95) aminosulfonyl group, the compound according to any one of [9] to

[11] and salts thereof, relates to.

Effect of the Invention

[0015] The compounds of the present invention or salts thereof have excellent pesticidal effects. They are effective not only against pests in the agricultural and horticultural fields but also against pests parasitizing pet animals such as dogs and cats or livestock such as cows and sheep.

Embodiments for Carrying Out the Invention

[0016] In the definitions of general formulas (1) and (2) of the compound of the present invention, "halo" means "halogen atom", and represents a chlorine atom, a bromine atom, an iodine atom or a fluorine atom.

[0017] The "(C1-C6) alkyl group" means, for example, a methyl group, an ethyl group, a normal propyl group, an isopropyl group, a normal butyl group, an isobutyl group, a secondary butyl group, a tertiary butyl group, a normal pentyl group, an isopentyl group, a tertiary pentyl group, a neopentyl group, a 2,3-dimethylpropyl group, a 1-ethylpropyl group, a 1-methylbutyl group, a 2-methylbutyl group, a normal hexyl group, an isohexyl group, a 2-hexyl group, a 3-hexyl group, a 2-methylpentyl group, a 3-methylpentyl group, a 1,1,2-trimethylpropyl group, a 3,3-dimethylbutyl group, etc., which are linear or branched alkyl groups having 1 to 6 carbon atoms.

[0018] The "(C2-C6) alkenyl group" means, for example, 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, a 3,3-dimethyl-1-butenyl group, etc., which are linear or branched alkenyl groups having 2 to 6 carbon atoms. The "(C2-C6) alkynyl group" means, for example, 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, a 3,3-dimethyl-1-butynyl group, etc., which are linear or branched alkynyl groups having 2 to 6 carbon atoms.

[0019] 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, a cyclohexyl group, etc. The "(C1-C6) alkoxy group" includes, for example, 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, a 1,1,2-trimethylpropyloxy group, etc., which are linear or branched alkoxy groups having 1 to 6 carbon atoms.

[0020] The "(C1-C6) alkylthio group" includes, for example, 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, a 1,1,2-trimethylpropylthio group, etc., which are linear or branched alkylthio groups having 1 to 6 carbon atoms.

[0021] Examples of the “(C1-C6) alkylsulfinyl group” include linear or branched alkylsulfinyl groups having 1 to 6 carbon atoms, such as 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, 1,1,2-trimethylpropylsulfinyl group, etc.

[0022] Examples of the “(C1-C6) alkylsulfonyl group” include linear or branched alkylsulfonyl groups having 1 to 6 carbon atoms, such as 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, 1,1,2-trimethylpropylsulfonyl group, etc.

[0023] The “(C1-C6) alkylcarbonyl group” refers to an alkylcarbonyl group having 2 to 7 carbon atoms, such as an acetyl group, propanoyl group, butanoyl group, 2-methylpropanoyl group, pentanoyl group, 2-methylbutanoyl group, 3-methylbutanoyl group, pivaloyl group, hexanoyl group, etc., which have the above-mentioned (C1-C6) alkyl group.

[0024] The "(C1-C6) alkylcarbonylamino group" refers to an alkylcarbonylamino group having 2 to 7 carbon atoms, 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, a hexanoylamino group, etc., which have the above-mentioned (C1-C6) alkyl group.

[0025] Examples of the "(C1-C6) alkylsulfonylamino group" include linear or branched alkylsulfonylamino groups having 1 to 6 carbon atoms, such as a methylsulfonylamino group, an ethylsulfonylamino group, a normal propylsulfonylamino group, an isopropylsulfonylamino group, a normal butylsulfonylamino group, a secondary butylsulfonylamino group, a tertiary butylsulfonylamino group, a normal pentylsulfonylamino group, an isopentylsulfonylamino group, a tertiary pentylsulfonylamino group, a neopentylsulfonylamino group, a 2,3-dimethylpropylsulfonylamino group, a 1-ethylpropylsulfonylamino group, a 1-methylbutylsulfonylamino group, a normal hexylsulfonylamino group, an isohexylsulfonylamino group, a 1,1,2-trimethylpropylsulfonylamino group, etc.

[0026] The "N-(C1-C6) alkylaminocarbonyl group" refers to an alkylaminocarbonyl group having 2 to 7 carbon atoms, such as an N-methylaminocarbonyl group, an N-ethylaminocarbonyl group, an N-normal propylaminocarbonyl group, an N-isopropylaminocarbonyl group, an N-normal butylaminocarbonyl group, an N-isobutylaminocarbonyl group, an N-secondary butylaminocarbonyl group, an N-tertiary butylaminocarbonyl group, an N-normal pentylaminocarbonyl group, an N-isopentylaminocarbonyl group, an N-tertiary pentylaminocarbonyl group, an N-neopentylaminocarbonyl group, an N-normal hexylaminocarbonyl group, an N-isohexylaminocarbonyl group, etc., which have a linear or branched alkyl group having 1 to 6 carbon atoms.

[0027] The "(C1-C6) alkoxycarbonyl group" refers to an alkoxycarbonyl group having 2 to 7 carbon atoms, such as a methoxycarbonyl group, an ethoxycarbonyl group, a normal propoxycarbonyl group, an isopropoxycarbonyl group, a normal butoxycarbonyl group, an isobutoxycarbonyl group, a secondary butoxycarbonyl group, a tertiary butoxycarbonyl group, a pentyloxycarbonyl group, etc., which are alkoxycarbonyl groups having the above-mentioned (C1-C6) alkoxy group.

[0028] 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, an N-(1,1,2-trimethylpropyl)aminosulfonyl group, etc.

[0029] Examples of the 「N,N-di(C1-C6)alkylaminosulfonyl group」 include linear or branched dialkylaminosulfonyl groups having 1 to 6 carbon atoms such as N,N-dimethylaminosulfonyl group, N,N-diethylaminosulfonyl group, N,N-dinormalpropylaminosulfonyl group, N,N-diisopropylaminosulfonyl group, N,N-dinormalbutylaminosulfonyl group, N,N-di-secondarybutylaminosulfonyl group, N,N-di-tertiarybutylaminosulfonyl group, N-methyl-N-ethylaminosulfonyl group, N-methyl-N-normalpropylaminosulfonyl group, N-methyl-N-isopropylaminosulfonyl group, N-methyl-N-normalbutylaminosulfonyl group, N-methyl-N-secondarybutylaminosulfonyl group, N-methyl-N-tertiarybutylaminosulfonyl group, N-methyl-N-normalpentylaminosulfonyl group, N-methyl-N-isopentylaminosulfonyl group, N-methyl-N-tertiarypentylaminosulfonyl group, N-methyl-N-neopentylaminosulfonyl group, N-methyl-N-(2,3-dimethylpropyl)aminosulfonyl group, N-methyl-N-(1-ethylpropyl)aminosulfonyl group, N-methyl-N-(1-methylbutyl)aminosulfonyl group, N-methyl-N-normalhexylaminosulfonyl group, N-methyl-N-isohexylaminosulfonyl group, N-methyl-N-(1,1,2-trimethylpropyl)aminosulfonyl group, etc.

[0030] Examples of the "N-(C1-C6) alkylamino group" include linear or branched alkylamino groups having 1 to 6 carbon atoms such as N-methylamino group, N-ethylamino group, N-normal propylamino group, N-isopropylamino group, N-normal butylamino group, N-secondary butylamino group, N-tertiary butylamino group, N-normal pentylamino group, N-isopentylamino group, N-tertiary pentylamino group, N-neopentylamino group, N-(2,3-dimethylpropyl)amino group, N-(1-ethylpropyl)amino group, N-(1-methylbutyl)amino group, N-normal hexylamino group, N-isohexylamino group, N-(1,1,2-trimethylpropyl)amino group, etc.

[0031] Examples of the "N,N-di(C1-C6) alkylamino group" include linear or branched dialkylamino groups having 1 to 6 carbon atoms such as N,N-dimethylamino group, N,N-diethylamino group, N,N-di-normal propylamino group, N,N-di-isopropylamino group, N,N-di-normal butylamino group, N,N-di-secondary butylamino group, N,N-di-tertiary butylamino group, N-methyl-N-ethylamino group, N-methyl-N-normal propylamino group, N-methyl-N-isopropylamino group, N-methyl-N-normal butylamino group, N-methyl-N-secondary butylamino group, N-methyl-N-tertiary butylamino group, N-methyl-N-normal pentylamino group, N-methyl-N-isopentylamino group, N-methyl-N-tertiary pentylamino group, N-methyl-N-neopentylamino group, N-methyl-N-(2,3-dimethylpropyl)amino group, N-methyl-N-(1-ethylpropyl)amino group, N-methyl-N-(1-methylbutyl)amino group, N-methyl-N-normal hexylamino group, N-methyl-N-isohexylamino group, N-methyl-N-(1,1,2-trimethylpropyl)amino group, etc.

[0032] Examples of the "N-(C1-C6) alkyl-N-phenylamino group" include linear or branched alkyl-N-phenylamino groups with 1 to 6 carbon atoms such as N-methyl-N-phenylamino group, N-ethyl-N-phenylamino group, N-n-propyl-N-phenylamino group, N-isopropyl-N-phenylamino group, N-n-butyl-N-phenylamino group, N-sec-butyl-N-phenylamino group, N-tert-butyl-N-phenylamino group, N-n-pentyl-N-phenylamino group, N-isopentyl-N-phenylamino group, N-tert-pentyl-N-phenylamino group, N-neopentyl-N-phenylamino group, N-(2,3-dimethylpropyl)-N-phenylamino group, N-(1-ethylpropyl)-N-phenylamino group, N-(1-methylbutyl)-N-phenylamino group, N-n-hexyl-N-phenylamino group, N-isohexyl-N-phenylamino group, N-(1,1,2-trimethylpropyl)-N-phenylamino group, etc.

[0033] One or more halogen atoms may be substituted at the substitutable positions of 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) alkylaminocarbonyl group", etc. When there are two or more halogen atoms to be substituted, the halogen atoms may be the same or different.

[0034] They are respectively represented as "halo(C1-C6)alkyl group", "halo(C2-C6)alkenyl group", "halo(C2-C6)alkynyl group", "halo(C1-C6)alkoxy group", "halo(C1-C6)alkylthio group", "halo(C1-C6)alkylsulfinyl group", "halo(C1-C6)alkylsulfonyl group", "halo(C3-C6)cycloalkyl group", "halo(C1-C6)alkylcarbonylamino group", "halo(C1-C6)alkylsulfonylamino group", "N-halo(C1-C6)alkylaminocarbonyl group", etc.

[0035] Expressions such as "(C1-C6)", "(C2-C6)", "(C3-C6)" indicate the range of the number of carbon atoms of various substituents. Furthermore, the above definition can also be shown for the group to which the above substituents are linked. For example, in the case of "(C1-C6)alkoxy(C1-C6)alkyl group", it indicates that a linear or branched alkoxy group with 1 to 6 carbon atoms is bonded to a linear or branched alkyl group with 1 to 6 carbon atoms.

[0036] The "aryl group" indicates an aromatic hydrocarbon group with 6 to 10 carbon atoms such as a phenyl group, 1-naphthyl group, 2-naphthyl group, etc.

[0037] <http: / / www.wipo.int / standards / fr / Examples of the "5- to 10-membered heterocyclic group" include a 5- or 6-membered monocyclic aromatic heterocyclic group containing 1 to 4 heteroatoms selected from oxygen atom, sulfur atom and nitrogen atom in addition to carbon atoms as ring-constituting atoms, an aromatic condensed heterocyclic group formed by condensation of the monocyclic aromatic heterocyclic ring with a benzene ring or a monocyclic aromatic ring, a 4- to 6-membered monocyclic non-aromatic heterocyclic group, or a non-aromatic condensed heterocyclic group formed by condensation of the monocyclic non-aromatic heterocyclic ring with a benzene ring or a monocyclic aromatic ring. The ring-constituting atoms of the above 5- to 10-membered heterocyclic group may be oxidized with an oxo group.

[0038] 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., 1,3,4-oxadiazolyl group, 1,2,4-oxadiazolyl group), a thiadiazolyl group (e.g., 1,3,4-thiadiazolyl group, 1,2,4-thiadiazolyl group), a triazolyl group (e.g., 1,2,4-triazolyl group), a tetrazolyl group, a triazinyl group (e.g., 1,3,5-triazinyl group, 1,2,4-triazinyl group), etc. 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, a thienopyridyl group, a pyrrolopyridyl group (e.g., pyrrolo[1,2-a]pyridyl group, pyrrolo[2,3-b]pyridyl group), an oxazolopyridyl group (e.g., oxazolo[3,2-a]pyridyl group, oxazolo[5,4-b]pyridyl group, oxazolo[4,5-b]pyridyl group), an isoxazolopyridyl group (e.g., isoxazolo[2,3-a]pyridyl group, isoxazolo[4,5-b]pyridyl group, isoxazolo[5,4-b]pyridyl group), a thiazolopyridyl group (e.g., thiazolo[3,2-a]pyridyl group, thiazolo[5,4-b]pyridyl group, thiazolo[4,5-b]pyridyl group), an isothiazolopyridyl group (e.g., isothiazolo[2,3-a]pyridyl group, isothiazolo[4,5-b]pyridyl group, isothiazolo[5,4-b]pyridyl group), an imidazopyridyl group (e.g., imidazo[1,2-a]pyridyl group, imidazo[4,5-b]pyridyl group), a pyrazolopyridyl group (e.g., pyrazolo[1,5-a]pyridyl group, pyrazolo[3,4-a]pyridyl group, pyrazolo[4,3-a]pyridyl group), an indolizinyl group, a triazolopyridyl group (e.g., [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 and the like.

[0039] Examples of the "monocyclic non-aromatic heterocyclic group" include, for example, oxetanyl group, thietanyl group, azetidinyl group, pyrrolidinyl group, pyrrolidinyl-2-one group, piperidinyl group, morpholinyl group, thiomorpholinyl group, piperazinyl group, hexamethyleneiminyl group, oxazolidinyl group, thiazolidinyl group, imidazolidinyl group, oxazolinyl group, thiazolinyl group, isoxazolinyl group, 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-dioxepan-2-yl group, pyranyl group, tetrahydropyranyl group, thiopyranyl group, tetrahydrothiopyranyl group, 1-oxidotetrahydrothiopyranyl group, 1,1-dioxidotetrahydrothiopyranyl group, tetrahydrofuranyl group, dioxanyl group, pyrazolidinyl group, pyrazolinyl group, tetrahydropyrimidinyl group, dihydrotriazolyl group, tetrahydrotriazolyl group and the like. Examples of the "non-aromatic fused heterocyclic group" include, for example, dihydroindolyl group, dihydroisoindolyl group, dihydrobenzofuranyl group, dihydrobenzodioxinyl group, dihydrobenzodioxepinyl group, tetrahydrobenzofuranyl group, chromenyl group, dihydroquinolinyl group, tetrahydroquinolinyl group, dihydroisoquinolinyl group, tetrahydroisoquinolinyl group, dihydrophthalazinyl group and the like.

[0040] R 2 and R 3They may combine with each other to form a ring. Examples of the "ring" include 3- to 7-membered nitrogen-containing heterocycles such as aziridine, azetidine, pyrrolidine, piperidine, homopiperidine, piperazine, homopiperazine, morpholine, and homomorpholine. The nitrogen-containing heterocycle may be condensed with a benzene ring. The nitrogen-containing heterocycle and the benzene ring may be substituted with 1 to 6 substituents selected from the group consisting of a halogen atom, a (C1-C6) alkyl group, a halo(C1-C6) alkyl group, and the like.

[0041] Examples of the salts of the compounds represented by the general formulas (1) and (2) 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.

[0042] The compounds represented by the general formulas (1) and (2) of the present invention and their salts may have one or more asymmetric centers in their structural formulas, and there may be two or more optical isomers and diastereomers. The present invention encompasses all of the individual optical isomers and mixtures containing them in any ratio. Also, the compounds represented by the general formulas (1) and (2) of the present invention and their salts may have two geometric isomers derived from a carbon-carbon double bond in their structural formulas, and the present invention encompasses all of the individual geometric isomers and mixtures containing them in any ratio. Furthermore, there may be multiple tautomers in the compounds represented by the general formulas (1) and (2) of the present invention and their salts, and the present invention encompasses all of the individual tautomers and mixtures containing them in any ratio.

[0043] The compounds represented by the general formulas (1) and (2) of the present invention are mesoionic inner salts and are also known as "zwitterions". An "inner salt" is an electrically neutral molecule, but carries positive and negative formal charges on different atoms in each valence bond structure based on the valence bond theory. Moreover, the molecular structure of the compound represented by the general formula (1) of the present invention can be represented by the valence bond structures shown in the following general formulas (1a) and (1b), and the molecular structure of the compound represented by the general formula (2) can be represented by the valence bond structures shown in the following general formulas (2a) and (2b), and in each, positive and negative formal charges are arranged on different atoms. Due to this resonance, the compounds represented by the general formulas (1) and (2) of the present invention are also called "mesoionic". Further, the valence bond structures shown in the general formulas (1), (1a), (1b), (2), (2a), and (2b) can also exist as tautomers shown in the following general formulas (1'), (1a'), (1b'), (2'), (2a'), and (2b), respectively. For the sake of simplicity, the molecular structures of the compounds represented by the general formulas (1) and (2) of the present invention are described as a single valence bond structure in the present disclosure and the claims. These specific valence bond structures should be understood as representatives of all the valence bond structures related to the bonds in the molecules of the compounds represented by the general formulas (1) and (2) of the present invention. Therefore, references to the compounds represented by the general formulas (1) and (2) of the present invention in the present disclosure and the claims relate to all applicable valence bond structures and other (e.g., molecular orbital theory) structures, unless otherwise specified. [Chemical formula] [Chemical formula]

[0044] In the compounds represented by the general formulas (1) and (2) of the present invention, the following preferred embodiments are shown. The compound represented by the general formula (2) is useful as a synthetic intermediate for the compound represented by the general formula (1).

[0045] In the general formula (1), R1 As the group, the groups of the above (a5), (a6), (a7), (a8), (a9), (a10), (a11), (a12), (a13), (a14), (a15), (a16), (a17), (a18), (a19), (a20), (a21), (a22), (a23), (a24), (a25), (a26), (a27), (a28), (a29), (a30), (a31), (a32), (a33), (a34), (a35), (a36), (a37), (a38), (a39), (a40), (a41), (a42), (a43), (a44), (a45), (a46), (a47), (a48), (a49), (a50), (a51), (a52), (a53), (a54), (a55), (a56), (a57), (a58), (a59), (a60), (a61), (a62), (a63), (a64), (a65), (a66), (a67), (a68), (a69), (a70), (a71), (a72), (a73), (a74), (a75), (a76), (a77), (a78), (a79), (a80), (a81), (a82), (a83), (a84), (a85), (a86), (a87), (a88), (a89), (a90), (a91), (a92), (a93), (a94), (a95), (a96), (a97), (a98), (a99), (a100), (a101), (a102), (a103), (a104), (a105), (a106), (a107), (a108), (a109), (a110), (a111), or (a112) are preferred, As the group, the groups of the above (a5), (a6), (a7), (a8), (a9), (a10), (a11), (a12), (a13), (a14), (a15), (a16), (a17), (a18), (a27), (a28), (a97), (a98), (a99), (a100), (a101), (a102), (a103), (a104), (a105), (a106), (a107), (a108), (a109), (a110), (a111), or (a112) are more preferred, As the group, the groups of the above (a5), (a6), (a7), (a8), (a13), (a14), (a99), or (a100) are even more preferred.

[0046] In general formula (1), R 2 is preferably a group of the above (b1), (b2), (b3), (b4), (b5), (b6), (b7), (b8), (b9), (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), (b54), (b55), (b58), (b59), (b60), (b61), (b62), (b63), (b64), (b65), (b66), (b67), (b68), (b69), or (b70), and more preferably a group of the above (b1), (b4), (b8), (b15), (b16), (b17), (b18), (b19), (b22), (b23), (b32), (b33), (b42), or (b43).

[0047] In general formula (1), R 3 is preferably a group of the above (c1), (c2), or (c3), and more preferably a hydrogen atom in (c1).

[0048] In general formula (1), Y is preferably an oxygen atom or a sulfur atom.

[0049] In general formula (1), Z is an oxygen atom, a sulfur atom, or NOR 4 group (wherein R 4 represents a hydrogen atom, a (C1-C6) alkyl group, or a halo (C1-C6) alkyl group.) is preferable, and more preferably an oxygen atom, a sulfur atom, or NOR 4 group (wherein R 4 represents a hydrogen atom.).

[0050] In general formula (1), as the substituent group A, it is preferably composed of the groups of (d1), (d2), (d6), (d7), (d8), (d9), (d10), (d11), (d12), (d13), (d14), (d15), (d16), (d17), (d18), (d19), (d20), (d21), (d22), (d23), (d26), (d27), (d32), (d33), (d36), (d37), (d38), (d39), (d40), (d41), (d42), (d43), (d52), (d53), (d54), (d55), (d56), (d57), (d58), (d59), (d60), (d61), (d62), (d63), (d64), (d65), (d66), (d67), (d68), (d69), (d70), (d71), (d72), (d73), (d95), and (d96) above. More preferably, it is composed of the groups of (d1), (d2), (d6), (d9), (d10), (d12), (d13), (d14), (d17), (d43), and (d95) above.

[0051] In general formula (1), as the substituent group B, it is preferably composed of the groups of (e1), (e2), (e3), (e4), (e5), (e6), (e7), (e8), (e9), (e10), (e11), and (e12) above. More preferably, it is composed of the groups of (e3) and (e4) above.

[0052] In general formula (1), as the substituent group C, it is preferably composed of the groups of (f1), (f2), and (f10) above.

[0053] In general formula (1), as the substituent group D, it is preferably composed of the groups of (g1), (g2), (g3), (g7), (g8), (g9), (g10), (g11), (g12), (g13), (g14), (g15), (g16), (g17), (g18), (g23), (g24), and (g25) above. It is more preferable that it consists of the groups of (g1), (g2), (g7), (g8), (g10), (g13), (g14), (g16), and (g24) described above.

[0054] In general formula (2), R 1 is preferably a group of (a5), (a6), (a7), (a8), (a9), (a10), (a11), (a12), (a13), (a14), (a15), (a16), (a17), (a18), (a19), (a20), (a21), (a22), (a23), (a24), (a25), (a26), (a27), (a28), (a29), (a30), (a31), (a32), (a33), (a34), (a35), (a36), (a37), (a38), (a39), (a40), (a41), (a42), (a43), (a44), (a45), (a46), (a47), (a48), (a49), (a50), (a51), (a52), (a53), (a54), (a55), (a56), (a57), (a58), (a59), (a60), (a61), (a62), (a63), (a64), (a65), (a66), (a67), (a68), (a69), (a70), (a71), (a72), (a73), (a74), (a75), (a76), (a77), (a78), (a79), (a80), (a81), (a82), (a83), (a84), (a85), (a86), (a87), (a88), (a89), (a90), (a91), (a92), (a93), (a94), (a95), (a96), (a97), (a98), (a99), (a100), (a101), (a102), (a103), (a104), (a105), (a106), (a107), (a108), (a109), (a110), (a111), (a112), The groups of (a5), (a6), (a7), (a8), (a9), (a10), (a11), (a12), (a13), (a14), (a15), (a16), (a17), (a18), (a27), (a28), (a97), (a98), (a99), (a100), (a101), (a102), (a103), (a104), (a105), (a106), (a107), (a108), (a109), (a110), (a111), or (a112) above are more preferable. The groups of (a5), (a6), (a7), (a8), (a13), (a14), (a99), or (a100) above are even more preferable.

[0055] In general formula (2), R 7 is preferably (h1) a (C1-C6) alkyl group; or (h2) a (C1-C6) alkoxy(C1-C6) alkyl group. (h1) A (C1-C6) alkyl group is preferable.

[0056] In general formula (2), as the substituent group A, it is preferably composed of the groups of (d1), (d2), (d6), (d7), (d8), (d9), (d10), (d11), (d12), (d13), (d14), (d15), (d16), (d17), (d18), (d19), (d20), (d21), (d22), (d23), (d26), (d27), (d32), (d33), (d36), (d37), (d38), (d39), (d40), (d41), (d42), (d43), (d52), (d53), (d54), (d55), (d56), (d57), (d58), (d59), (d60), (d61), (d62), (d63), (d64), (d65), (d66), (d67), (d68), (d69), (d70), (d71), (d72), (d73), (d95), and (d96) above. It is more preferably composed of the groups of (d1), (d2), (d6), (d9), (d10), (d11), (d12), (d13), (d14), (d17), (d43), (d61), and (d95) above.

[0057] The various compounds of the present invention can be produced, for example, by the following production methods, but the present invention is not limited thereto.

[0058] Production Method 1 The compound represented by the general formula (1-1) of the present invention can be produced from the compound represented by the general formula (2) by the following step [a].

Chemical formula

[0059] {In the formula, R 1 , R 2 , R 3 and R 7 are the same as defined above.}

[0060] Production method of step [a] The compound represented by the general formula (1-1) of the present invention can be produced by reacting the compound represented by the general formula (2) with the compound represented by the general formula (3) in the presence of an inert solvent.

[0061] Examples of the inert solvent that can be used in this reaction include chain or cyclic saturated hydrocarbons such as pentane, hexane, and cyclohexane; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as methylene chloride, chloroform, and carbon tetrachloride; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; chain or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, and tetrahydrofuran; nitriles such as acetonitrile and propionitrile; esters such as methyl acetate; ketones such as acetone and methyl ethyl ketone; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, and 1,3-dimethyl-2-imidazolidinone; and alcohols such as methanol, ethanol, propanol, butanol, and 2-propanol. These inert solvents can be used alone or in combination of two or more. The amount used may be appropriately selected from the range of usually 0.1 to 100 L per 1 mol of the compound represented by the general formula (2).

[0062] Since this reaction is an equimolar reaction, each compound may be used in an equimolar amount, but any one of the compounds may also be used in excess. The reaction temperature in this reaction may generally be in the range from 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 generally be appropriately selected from 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 if necessary, the target product can be produced by purification by recrystallization, column chromatography, etc.

[0063] Production Method 2 The compound represented by the general formula (1-1) of the present invention can be produced from the compound represented by the general formula (4) by the above step [a] in the presence of dissolved oxygen. The reaction conditions of [a] are the same as described above. [Chemical formula]

[0064] {In the formula, R 1 、R 2 、R 3 and R 7 are the same as described above.}

[0065] Production Method 3 The compound represented by the general formula (1-2) of the present invention can be produced from the compound represented by the general formula (5) by the following step [b]. [Chemical formula]

[0066] {In the formula, R 1 、R 2 、R 3 and Y are the same as described above. Z' represents an oxygen atom or a sulfur atom.}

[0067] Production method of step [b] The compound represented by the general formula (1-2) can be produced by reacting the compound represented by the general formula (5) with an oxidizing agent in the presence of an inert solvent.

[0068] Examples of the oxidizing agent that can be used in this reaction include peroxides such as hydrogen peroxide solution, perbenzoic acid, metachloroperbenzoic acid, Oxone (registered trademark) (potassium hydrogen persulfate·potassium bisulfate·potassium sulfate), etc. These oxidizing agents can be appropriately selected from the range of 1 to 10 times the molar amount of the compound represented by the general formula (5).

[0069] Examples of the inert solvent that can be used in this reaction include chain or cyclic ethers such as diethyl ether, tetrahydrofuran, and dioxane; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as methylene chloride, chloroform, and carbon tetrachloride; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; nitriles such as acetonitrile; esters such as ethyl acetate; organic acids such as formic acid and acetic acid; polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, 1,3-dimethyl-2-imidazolidinone, and water; and alcohols such as methanol, ethanol, propanol, butanol, and 2-propanol. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent used is not particularly limited as long as it can dissolve the reaction reagents, and it can be appropriately selected from the range of 0.5 L to 100 L per 1 mol of the compound represented by the general formula (5).

[0070] The reaction temperature in this reaction is usually in the range from 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 it can be appropriately selected from the range of usually several minutes to 48 hours. After the reaction is completed, the target product can 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] Production Method 4 The compound represented by the general formula (1-2) of the present invention can be produced from the compound represented by the general formula (5) by the following step [c].

Chemical formula

[0072] {In the formula, R 1 , R 2 , R 3 and Y are the same as above. Z' represents an oxygen atom or a sulfur atom.}

[0073] Production method of step [c] The compound represented by the general formula (5) can be used to produce the compound represented by the general formula (1-2) by oxidation with dissolved oxygen in the presence of a base, a quaternary ammonium salt, and an inert solvent.

[0074] Examples of the base that can be used in this reaction include hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, etc., alkoxides such as sodium methoxide, sodium ethoxide, sodium tertiary butoxide, potassium tertiary butoxide, etc., alkali metal hydrides such as sodium hydride, potassium hydride, etc., carbonates such as lithium carbonate, lithium hydrogen carbonate, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate, calcium carbonate, magnesium carbonate, cesium carbonate, etc., acetates such as lithium acetate, sodium acetate, potassium acetate, etc., and organic bases such as pyridine, picoline, lutidine, triethylamine, tributylamine, N,N-diisopropylethylamine, etc. The amount used is usually in the range of 1 to 10 times the molar amount of the compound represented by the general formula (5).

[0075] Examples of the quaternary ammonium salt that can be used in this reaction include tetramethylammonium chloride, tetra-n-butylammonium fluoride, tetra-n-butylammonium chloride, tetra-n-butylammonium bromide, tetra-n-butylammonium iodide, trinormalbutylbenzylammonium chloride, etc. The amount used is usually in the range of 0.01 to 1 times the molar amount of the compound represented by the general formula (5).

[0076] Examples of the inert solvent that can be used in this reaction 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 tert-butyl ether, dioxane, and tetrahydrofuran; nitriles such as acetonitrile and propionitrile; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, and 1,3-dimethyl-2-imidazolidinone; and alcohols such as methanol, ethanol, propanol, butanol, and 2-propanol. These inert solvents can be used alone or in combination of two or more. The amount used may be appropriately selected from the range of usually 0.1 to 100 L per 1 mol of the compound represented by the general formula (5).

[0077] The reaction temperature in this reaction may usually be in the range from about 0 °C to the boiling point of the solvent used. The reaction time varies depending on the reaction scale, reaction temperature, etc. and is not constant, but may usually be appropriately selected from the range of several minutes to 48 hours. After completion of the reaction, the target product can be isolated from the reaction system containing the target product by a conventional method, and if necessary, the target product can be produced by purification by recrystallization, column chromatography, etc.

[0078] Production Method 5 The compound represented by the general formula (1-3) of the present invention can be produced from the compound represented by the general formula (5) by the following step [d].

Chemical formula

[0079] {In the formula, R 1 , R 2 , R 3 , R 4 and Y are the same as above. Z' represents an oxygen atom or a sulfur atom.}

[0080] Manufacturing method of step [d] The compound represented by general formula (1-3) of the present invention can be produced by reacting the compound represented by general formula (5) with the compound represented by general formula (6) in the presence of an inert solvent and dissolved oxygen.

[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 tertiary butoxide, and potassium tertiary 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 N,N-diisopropylethylamine. The amount of base used is usually in the range of 1 to 10 times the molar amount of the compound represented by formula (5).

[0082] The inert solvent that can be 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, 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 (5).

[0083] Since this reaction is an equimolar reaction, each compound can be used in an equimolar amount, but any of the compounds can also be used in excess. The reaction temperature in this reaction is usually in the range from 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 can usually be appropriately selected in the range of several minutes to 48 hours. After the reaction is completed, the target product can be isolated from the reaction system containing the target product by a conventional method, and if necessary, the target product can be produced by purification by recrystallization, column chromatography, etc.

[0084] Production Method 1 of Intermediate The compound represented by the general formula (2), which is an intermediate of the compound represented by the general formula (1-1) of the present invention, can be produced from the compound represented by the general formula (7) by the following production method, that is, step [e]. The compound represented by the general formula (7) can be produced by the method described in International Publication No. 2021 / 261563 pamphlet or according to it.

Chemical Formula

[0085] {In the formula, R 1 and R 7 are the same as above. R' represents a (C1-C6) alkyl group such as a methyl group or an ethyl group.}

[0086] Production Method of Step [e] The compound represented by the general formula (2) can be produced by subjecting the compound represented by the general formula (7) to a cyclization reaction in the presence of a base, an inert solvent and dissolved oxygen.

[0087] 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 tertiary butoxide, and potassium tertiary 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 (7).

[0088] 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 (7).

[0089] In this reaction, the reaction temperature can generally be in the range from about 0 °C to the boiling point of the solvent used. The reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but it can usually be appropriately selected within the range of several minutes to 48 hours. After the reaction is completed, the target product can be isolated from the reaction system containing the target product by a conventional method, and if necessary, the target product can be produced by purification using recrystallization, column chromatography, etc. It can also be used in the next step without isolation.

[0090] Production Method 1 of Starting Material The compound represented by the general formula (4) as the starting material can be produced by the method described in International Publication No. 2021 / 261563 pamphlet or according thereto.

[0091] Production Method 2 of Starting Material Among the compounds represented by the general formula (5) as the starting material, the compound in which Z' is an oxygen atom can be produced by the method described in International Publication No. 2021 / 261563 pamphlet or according thereto.

[0092] Production Method 3 of Starting Material Among the compounds represented by the general formula (5) as the starting material, the compound (5-1) in which Z' is a sulfur atom can be produced from the compound represented by the following general formula (8) by the following steps [f], [g] and [h]. The compound represented by the general formula (8) can be produced by the method described in International Publication No. 2021 / 261563 pamphlet or according thereto.

Chemical Formula

[0093] {In the formula, R 1 , R 2 , R 3 and Y are the same as above. R' represents a (C1-C6) alkyl group such as a methyl group, an ethyl group, a tertiary butyl group, etc., and L represents a leaving group such as chlorine, bromine, a (C1-C6) alkoxycarbonyloxy group, etc.}

[0094] Manufacturing method of step [f] A compound represented by general formula (10) can be produced by reacting a compound represented by general formula (8) with a compound represented by general formula (9) in the presence of a base and an inert solvent.

[0095] Examples of the base that can be used in this reaction include hydroxides of alkali metal atoms such as sodium hydroxide, potassium hydroxide, etc.; hydrides of alkali metals such as sodium hydride, potassium hydride, etc.; alkali metal salts of alcohols such as sodium ethoxide, potassium t-butoxide, etc.; carbonates such as sodium carbonate, potassium carbonate, sodium hydrogencarbonate, etc.; and organic bases such as triethylamine, pyridine, N,N-dimethyl-4-aminopyridine, DBU, etc., and 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 (8).

[0096] The inert solvent that can be 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, etc., 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 mentioned. These inert solvents can be used alone or in combination of two or more. The amount used may be appropriately selected usually from the range of 0.1 to 100 L per mole of the compound represented by the general formula (8).

[0097] Since this reaction is an equimolar reaction, each compound may be used in equimolar amounts, but any one of the compounds can also be used in excess. The reaction temperature in this reaction is usually in the range from 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 it may usually be appropriately selected in the range of several minutes to 48 hours. After completion of the reaction, the target product can be isolated from the reaction system containing the target product by a conventional method, and if necessary, the target product can be produced by purification by recrystallization, column chromatography, etc. Also, it can be used in the next step without isolation.

[0098] Production method of step [g] A compound represented by the general formula (11) can be produced by reacting a compound represented by the general formula (10) with a sulfurizing agent in the presence of an inert solvent.

[0099] Examples of the sulfurizing agent that can be used in this reaction include Lawesson’s Reagent, phosphorus pentasulfide, etc., and the amount used is usually in the range of 1.0 to 10 times the molar amount of the compound represented by the general formula (10).

[0100] This reaction may or may not use a solvent. Any solvent that does not significantly inhibit the progress of this reaction can be used. For example, chain or cyclic saturated hydrocarbons such as pentane, hexane, and cyclohexane; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; inert solvents such as chain or cyclic ethers like diethyl ether, methyl tert-butyl ether, dioxane, and tetrahydrofuran; nitriles such as acetonitrile and propionitrile; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, and 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, propanol, butanol, and 2-propanol. These inert solvents can be used alone or in a mixture of two or more. The amount used can be appropriately selected from the range of usually 0.1 to 100 L per mole of the compound represented by the general formula (10).

[0101] The reaction temperature in this reaction can usually be carried out in the range from about 0 °C to the boiling point of the solvent used. The reaction time varies depending on the reaction scale, reaction temperature, etc. and is not constant, but can usually be appropriately selected from the range of several minutes to 48 hours. After the reaction is completed, the target product can be isolated from the reaction system containing the target product by conventional methods. If necessary, the target product can be produced by purification using recrystallization, column chromatography, etc. Also, it can be used in the next step without isolation.

[0102] Production method of step [h] The compound represented by the general formula (11) can be hydrolyzed in the presence or absence of an acid and an inert solvent to produce the compound represented by the general formula (5-1).

[0103] Examples of the acid that can be used in this reaction include inorganic acids such as hydrochloric acid, sulfuric acid, and nitric acid; organic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, and benzoic acid; sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid, and p-toluenesulfonic acid; and phosphoric acid. The amount of the acid used may be appropriately selected from the range of 0.01 to 10 times the molar amount of the compound represented by the general formula (11), and the acid can also be used as a solvent.

[0104] Any inert solvent that does not significantly inhibit the progress of this reaction may be used. Examples of inert solvents include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as methylene chloride, chloroform, and carbon tetrachloride; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; linear or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, and tetrahydrofuran; esters such as ethyl acetate; amides such as N,N-dimethylformamide and N,N-dimethylacetamide; ketones such as acetone and methyl ethyl ketone; and polar solvents such as dimethyl sulfoxide and 1,3-dimethyl-2-imidazolidinone. These inert solvents may be used alone or in combination. The amount of inert solvent used is not particularly limited as long as it is an amount that dissolves the reaction reagents, and may be appropriately selected from the range of 0.5 L to 100 L per mole of the compound represented by general formula (11). Furthermore, when the acid is used as the solvent, no solvent is required.

[0105] The reaction temperature can be from room temperature to the boiling point of the inert solvent used, and the reaction time varies depending on the reaction scale and reaction temperature, but may be appropriately selected from 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 the product by recrystallization, column chromatography, etc. as necessary. The target product may also be subjected to the next step without isolation.

[0106] Representative examples of the compounds represented by general formulas (1) and (2) of the present invention are illustrated in Tables 1 to 4 below, but the present invention is not limited thereto. In the tables, "Me" represents a methyl group, "Et" represents an ethyl group, "c-Pr" represents a cyclopropyl group, "t-Bu" represents a tertiary butyl group, and "Ph" represents a phenyl group. Physical properties are melting point (°C) or H 1 -NMR. The H 1 -NMR data are shown in Table 5.

[0107]

Chemical formula

[0108]

Table 1

[0109]

Table 2

[0110]

Table 3

[0111]

Table 4

[0112]

Table 5

[0113]

Table 6

[0114]

Chemical formula

[0115] [Table 7]

[0116] [ka]

[0117] [Table 8]

[0118] [ka]

[0119] [Table 9]

[0120] [Table 10]

[0121] [Table 11]

[0122] [Table 12]

[0123] 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 and forestry, horticultural and grain storage pests, sanitary pests, nematodes and other pests that harm paddy rice, fruit trees, vegetables, other crops and ornamental plants. Furthermore, agricultural and horticultural insecticides containing the compound represented by general formula (1) of the present invention or a salt thereof as an active ingredient have excellent environmental safety, such as physical properties suitable for various labor-saving application methods, systemic activity, and appropriate soil persistence. Furthermore, 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 has little impact on beneficial insects such as natural enemies, the European honey bee, the bumblebee, and environmental organisms such as mayflies.

[0124] Examples of the above pests or nematodes are as follows. Examples of pests of the order Lepidoptera (Lepidoptera) include 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, potato leaf moth (Brachmia triannulella), bag moth (Monema flavescens), nettle looper moth (Trichoplusia ni), turmeric moth (Pleuroptya ruralis), plum geometries (Cystidia couaggaria), blue-striped silver butterfly (Lampides boeticus), Japanese hawk moth (Cephonodes hylas), cotton bollworm (Helicoverpa armigera), large bird moth (Phalerodonta manleyi), Japanese silk moth (Eumeta japonica), large cabbage white (Pieris brassicae), banded moth (Malacosoma neustria testacea), persimmon stalk moth (Stathmopoda masinissa), persimmon leaf moth (Cuphodes diospyrosella), and Japanese rice tortrix moth (Archips xylosteanus, turnip cutworm moth (Agrotis segetum), sweet potato moth (Tetramoera schistaceana), swallowtail butterfly (Papilio machaon hippocrates), yellow-spotted bat (Endoclyta sinensis), silver leafminer moth (Lyonetia prunifoliella), silver leafminer moth (Phyllonorycterringoneella), Cydia kurokoi, Eucoenogenes aestuosa, Lobesia botrana, Latoia sinica, Euzophera batangensis, Phalonidia mesotypa, Spilosoma imparilis, Glyphodes pyloalis, Olethreutes mori, Tineola bisselliella, Endoclyta excrescens, Nemapogon granellus, Synanthedon hector, Cydia pomonella, Plutella xylostella, Cnaphalocrocis medinalis, Sesamia calamistis, Scirpophaga incertulas, Pediasia teterrellus, Phthorimaea operculella, Stauropus fagi persimilis, Etiella zinckenella, Spodoptera exigua, Palpifer sexnotata, Spodoptera mauritia, Scirpophaga innotata, Xestia c-nigrum, Spodoptera depravata, Ephestia kuehniella, Angerona prunaria, Clostera anastomosis, Pseudoplusia includens, Matsumuraeses falcana, Helicoverpaassulta), Autographa nigrisigna, Agrotis ipsilon, Euproctis pseudoconspersa, Adoxophyes orana, Caloptilia theivora, Homona magnanima, Ephestia elutella, Eumeta minuscula, Clostera anachoreta, Heliothis maritima, Sparganothis pilleriana, Busseola fusca, Euproctis subflava, Biston robustum, Heliothis zea, Aedia leucomelas, Narosoideus flavidorsalis, Viminia rumicis, Bucculatrix pyrivorella, Grapholita molesta, Spulerina astaurota, Ectomyelois pyrivorella, Chilo suppressalis, Acrolepiopsis sapporensis, Plodia interpunctella, Hellula undalis, Sitotroga cerealella, Spodoptera litura, Eucosma aporema, Acleris comariana, 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, Leguminivora glycinivorella, Maruca testulalis, Matsumuraeses phaseoli, Caloptilia soyella, Phyllocnistis citrella, Omiodes indicate, Archips fuscocupreanus, Acanthoplusia agnata, Bambalina sp., Carposina niponensis, Conogethes punctiferalis, Synanthedon sp., Lyonetia clerkella, Papilio helenus, Colias erate poliographus, Phalera flavescens, Pieris rapae crucivora, Pieris rapae and other white butterflies, Euproctis similis, Acrolepiopsis suzukiella, Ostrinia nubilalis, Mamestra brassicae, Ascotisselenaria, Artemis longiflora moth (Ptheochroides clandestina), Large apple tortrix moth (Hoshinoa adumbratana), Apple moth (Odonestis pruni japonensis), Apple shriveling moth (Triaena intermedia), Smaller apple tortrix moth (Adoxophyes orana fasciata), Small apple fruit moth (Grapholita inopinata), White apple tortrix moth (Spilonota ocellana), Grey apple tortrix moth (Spilonota lechriaspis), Black apple moth (Illiberis pruni), Small apple fruit moth (Argyresthia conjugella), Leaf moth (Caloptilia zachrysa), Common apple tortrix moth (Archips breviplicanus), Red cotton bollworm (Anomis flava), Pink bollworm (Pectinophora gossypiella, cotton bollworm (Notarcha derogata), cotton leaf moth (Diaphania indica), false tobacco budworm (Heliothis virescens), and cotton ringworm (Earias cupreoviridis).

[0125] Hemiptera (Hemiptera) pests include, for example, the green grass bug (Nezara antennata), the red-striped rice bug (Stenotus rubrovittatus), the red-striped rice bug (Graphosoma rubrolineatum), the red-bearded green rice bug (Trigonotylus coelestialium), the red-spotted leaf bug (Aeschynteles maculatus), the red-spotted rice bug (Creontiades pallidifer), the red-spotted rice bug (Dysdercus cingulatus), the red-spotted scale bug (Chrysomphalus ficus), the red-spotted scale bug (Aonidiella aurantii), and the brown cicada (Graptopsaltria nigrofuscata), American long-winged stink bug (Blissusleucopterus), Icerya scale (Icerya purchasi), striped stink bug (Piezodorus hybneri), rice stink bug (Lagynotomus elongatus), rice yellow leafhopper (Thaia subrufa), black rice stink bug (Scotinophara lurida), thorny long-horned aphid (Sitobion ibarae), Iwasaki stink bug (Stariodes iwasakii), pale scale (Aspidiotus destructor), pale green rice bug (Taylorilygus pallidulus), plum horn aphid (Myzusmumecola), plum white scale (Pseudaulacaspis prunicola), pea aphid (Acyrthosiphon pisum), spider bug (Anacanthocoris striicornis), black-spotted stink bug (Ectometopterus micantulus), large spur-spotted spotted stink bug (Eysarcoris lewisi), large leaf bug (Molipteryx fuliginosa), Japanese giant leafhopper (Cicadella viridis), green aphid (Rhopalosophumrufiabdominalis), Saissetia oleate, Trialeurodes vaporariorum, Aguriahana quercus, Lygus spp., Euceraphis punctipennis, Andaspis kashicola, Coccus pseudomagnoliarum, Cavelerius saccharivorus, Galeatus spinifrons, Macrosiphoniella sanborni, Aonidiella citrina, Halyomorpha mista, Stephanitis fasciicarina, Trioza camphorae, Leptocorisa chinensis, Trioza quercicola, Uhlerites latius, Erythroneura comes, Paromius exiguus, Duplaspidiotus claviger, Nephotettix nigropictus, Halticiellus insularis, Perkinsiella saccharicida, Psylla malivorella, Anomomeura mori, Pseudococcus longispinis, Pseudaulacaspis pentagona, Pulvinaria kuwacola, Apolygus lucorum, 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, Empoasca onukii, Plautia stali, Dysaphis tulipae, Macrosiphum euphorbiae, Stephanitis pyrioides, Ceroplastesceriferus), Parlatoria camelliae, Apolygus spinolai, Nephotettix cincticeps, Glaucias subpunctatus, Orthotylus flavosparsus, Rhopalosiphum maidis, Peregrinus maidis, Eysarcoris parvus, Cimex lectularius, Psylla abieti, Nilaparvata lugens, Psylla tobirae, Eurydema rugosum, Schizaphis piricola, Psylla pyricola, Parlatoreopsis pyri, Stephanitis nashi, Dysmicoccus wistariae, Lepholeucaspis japonica, Sappaphis piri, Lipaphis erysimi, Neotoxoptera formosana, Rhopalosophum nymphaeae, Edwardsianarosae, Pinnaspisaspidistrae, Psylla alni, Speusotettix subfusculus, Alnetoidia alneti, Sogatella panicicola, Adelphocoris lineolatus, Dysdercus poecilus, Parlatoria ziziphi, 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 triannulatus, Viteus vitifolii, Acanthocoris sordidus, Leptocorisa acuta, Macropes obnubilus, Cletus punctiger, Riptortus clavatus, Paratrioza cockerelli, Aphrophora costalis, Lygus disponsi, Lygus saundersi, Crisicoccus pini, Empoasca abietis, Crisicoccus matsumotoi, Aphis craccivora, Megacopta punctatissimum, Eysarcoris guttiger, Lepidosaphes beckii, Diaphorina citri, Toxoptera citricidus, Planococcuscitri), Dialeurodes citri, Aleurocanthus spiniferus, Pseudococcus citriculus, Zyginella citri, Pulvinaria citricola, Coccus discrepans, Pseudaonidia duplex, Pulvinaria aurantii, Lecanium corni, Nezara viridula, Stenodema calcaratum, Rhopalosiphum padi, Sitobion akebiae, Schizaphis graminum, Sorhoanus tritici, Brachycaudus helichrysi, Carpocoris purpureipennis, Myzus persicae, Hyopterus pruni, Aphis farinose yanagicola, Metasalis populi, Unaspis yanonensis, Mesohomotoma camphorae, Aphis spiraecola, Aphis pomi, Lepidosaphes ulmi, Psylla mali, Heterocordylus flavipes, Myzus malisuctus, Aphidonuguis mali, Orientus ishidai, Ovatussuch as *malicolens*, *Eriosoma lanigerum*, *Ceroplastes rubens*, and *Aphis gossypii*.

[0126] As Coleoptera (Coleoptera) pests, for example, Xystrocera globosa, Paederus fuscipes, Eucetonia roelofsi, Callosobruchus chinensis, Cylas formicarius, Hypera postica, Echinocnemus squameus, Oulema oryzae, Donacia provosti, Lissorhoptrus oryzophilus, Colasposoma dauricum, Euscepes postfasciatus, Epilachna varivestis, Acanthoscelides obtectus, Diabrotica virgifera virgifera, Involvulus cupreus, Aulacophora femoralis, Bruchus pisorum, Epilachna vigintioctomaculata, Carpophilus dimidiatus, Cassida nebulosa, Luperomorpha tunebrosa, Phyllotreta striolata, Psacothea hilaris, Aeolesthes chrysothrix, Curculio sikkimensis, Carpophilus hemipterus, Oxycetonia jucunda, Diabrotica spp.)、Japanese beetle (Mimela splendens), maize weevil (Sitophilus zeamais), red flour beetle (Tribolium castaneum), rice weevil (Sitophilus oryzae), lesser grain borer (Palorus subdepressus), Japanese cockchafer (Melolontha japonica), citrus longhorn beetle (Anoplophora malasiaca), litter beetle (Neatus picipes), Colorado potato beetle (Leptinotarsa decemlineata), southern corn rootworm (Diabrotica undecimpunctata howardi), sugarcane beetle (Sphenophorus venatus), fourteenth-spotted asparagus beetle (Crioceris quatuordecimpunctata), plum curculio (Conotrachelus nenuphar), turnip flea beetle (Ceuthorhynchidius albosuturalis), cabbage leaf beetle (Phaedon brassicae), cigarette beetle (Lasioderma serricorne), Japanese bean weevil (Sitona japonicus), Asiatic garden beetle (Adoretus tenuimaculatus), mealworm beetle (Tenebrio molitor), bean leaf beetle (Basilepta balyi), alfalfa weevil (Hypera nigrirostris), sugarbeet flea beetle (Chaetocnema concinna), copper chafer (Anomala cuprea), long-horned chafer (Heptophylla picea), twenty-eight-spotted ladybird (Epilachna vigintioctopunctata), northern corn rootworm (Diabrotica longicornis), flower chafer (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 stalk weevil (Phyllobius armatus), apple blossom weevil (Anthonomus pomorum), blue leaf beetle (Linaeidea aenea), and boll weevil (Anthonomus grandis).

[0127] As Diptera (fly order) pests, for example, Culex pipiens pallens, Pegomya hyoscyami, Liriomyza huidobrensis, Musca domestica, Chlorops oryzae, Hydrellia sasakii, Agromyza oryzae, Hydrellia griseola, Ophiomyia phaseoli, Dacus cucurbitae, Drosophila suzukii, Rhacochlaena japonica, Muscina stabulans, Megaselia spiracularis and other fly species such as 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), Sciarid gnat (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, bean leafminer (Liriomyza trifolii), tomato leafminer (Liriomyza sativae), oriental fruit fly (Dacus dorsalis), citrus fly (Dacus tsuneonis), wheat gall midge (Sitodiplosis mosellana), wheat stem miner (Meromuza nigriventris), Mexican fruit fly (Anastrepha ludens), and apple fruit fly (Rhagoletis pomonella).

[0128] Examples of Hymenoptera (bee) pests include, for example, Pristomyrmex pungens, wasps, Monomorium pharaohnis, Pheidole noda, Athalia rosae, Dryocosmus kuriphilus, Formica fusca japonica, sawflies, Athalia infumata infumata, Arge pagana, Athalia japonica, Acromyrmex spp., Solenopsis spp., Arge mali, and Ochetellus glaber, etc.

[0129] Examples of Orthoptera (grasshopper) pests include, for example, Homomorocoryphus lineosus, Gryllotalpa sp., Oxya hyla intricata, Oxya yezoensis, Locusta migratoria, Oxya japonica, Homomorocoryphus jezoensis, and Teleogryllus emma, etc.

[0130] As thrips pests, for example, Selenothrips rubrocinctus, Stenchaetothrips biformis, Haplothrips aculeatus, Ponticulothrips diospyrosi, Thrips flavus, Anaphothrips obscurus, Liothrips floridensis, Thrips simplex, Thrips nigropilosus, Heliothrips haemorrhoidalis, Pseudodendrothrips mori, Microcephalothrips abdominalis, Leeuwenia pasanii, Litotetothrips pasaniae, Scirtothrips citri, Haplothrips chinensis, Mycterothrips glycines, Thrips setosus, Scirtothrips dorsalis, Dendrothrips minowai, Haplothrips niger, Thrips tabaci, Thrips alliorum, Thrips hawaiiensis, Haplothrips kurdjumovi, Chirothrips manicatus, Frankliniella intonsa, Thrips coloratus, Franklinella occidentalis, Thripspalmi), Frankliniella lilivora, and Liothrips vaneeckei.

[0131] Examples of mite pests include mites such as Leptotrombidium akamushi, Tetranychus ludeni, Dermacentor variabilis, Tetranychus truncatus, Ornithonyssus bacoti, Demodex canis, Tetranychus viennensis, Tetranychus kanzawai, Rhipicephalus sanguineus, Cheyletus malaccensis, Tyrophagus putrescentiae, Dermatophagoides farinae, 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, Brevipalpus phoenicis, Octodectes cynotis, Dermatophagoides ptrenyssnus, Haemaphysalis flava, IxodesExamples include Tetranychus urticae, Phyllocoptruta citri, Aculus schlechtendali, Panonychus ulmi, Amblyomma americanum, Dermanyssus gallinae, Rhyzoglyphus robini, Sancassania sp., etc.

[0132] Examples of Isoptera 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, Reticulitermes speratus, etc.

[0133] Examples of cockroach pests include, for example, the smokybrown cockroach (Periplaneta fuliginosa), the German cockroach (Blattella germanica), the oriental cockroach (Blatta orientalis), the brown cockroach (Periplaneta brunnea), the Asian cockroach (Blattella lituricollis), the Japanese cockroach (Periplaneta japonica), and the American cockroach (Periplaneta americana), etc.

[0134] Examples of flea pests include, for example, the human flea (Pulex irritans), the cat flea (Ctenocephalides felis), and the pigeon flea (Ceratophyllus gallinae), etc.

[0135] Examples of nematodes include, for example, the stubby root nematode (Nothotylenchus acris), the rice white tip nematode (Aphelenchoides besseyi), the root-lesion nematode (Pratylenchus penetrans), the northern root-knot nematode (Meloidogyne hapla), the southern root-knot nematode (Meloidogyne incognita), the potato cyst nematode (Globodera rostochiensis), the Javanese root-knot nematode (Meloidogyne javanica), the soybean cyst nematode (Heterodera glycines), the coffee root-lesion nematode (Pratylenchus coffeae), the wheat root-lesion nematode (Pratylenchus neglectus), and the citrus nematode (Tylenchus semipenetrans), etc.

[0136] Examples of mollusks include, for example, Pomacea canaliculata, Achatina fulica, Meghimatium bilineatum, Lehmannina valentiana, Limax flavus, and Acusta despecta sieboldiana, etc.

[0137] In addition, the pesticidal agent for agricultural and horticultural use of the present invention also has a strong pesticidal effect against Tuta absoluta as other pests.

[0138] As examples of animal parasitic mites, which are one of the pests to be controlled, for example, 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; mites such as Dermanyssus gallinae, Ornithonyssus sylviarum, and Ornithonyssus bursa; trombiculid mites such as Eutrombicula wichmanni, Leptotrombidium akamushi, Leptotrombidium pallidum, Leptotrombidium fuji, Leptotrombidium tosa, Neotrombicula autumnalis, Eutrombicula alfreddugesi, and Helenicula miyagawai; Cheyletiella yasguri, CheyletiellaParasitivorax), and mites such as Cheyletiella blakei, Psoroptes cuniculi, Chorioptes bovis, Otodectes cynotis, Sarcoptes scabiei, and Notoedres cati, and demodex mites such as Demodex canis, etc.

[0139] Examples of other pests to be controlled include external parasitic wingless insects belonging to the order Siphonaptera, more specifically, fleas belonging to the families Pulicidae and Ceratophyllus. Examples of fleas belonging to the family Pulicidae include Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Echidnophaga gallinacea, Xenopsylla cheopis, Leptopsylla segnis, Nosopsyllus fasciatus, and Monopsyllus anisus.

[0140] Further examples of external parasites to be controlled include lice such as cattle lice (Haematopinus eurysternus), horse lice (Haematopinus asini), sheep lice (Dalmalinia ovis), cattle lice (Linognathus vituli), pig lice (Haematopinus suis), pubic lice (Phthirus pubis), and head lice (Pediculus capitis), as well as biting lice such as dog lice (Trichodectes canis), and blood-sucking dipteran pests such as horse flies (Tabanus trigonus), cow midges (Culicoides schultzei), and black 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 genus Diphyllobothrix gonorrhoeae, 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.

[0141] The agricultural and horticultural insecticides of the present invention, which contain the compound represented by formula (1) or a salt thereof as an active ingredient, have a significant control effect against pests that cause damage to paddy field crops, field crops, fruit trees, vegetables, other crops, and flowers, etc., and therefore the expected effects of the agricultural and horticultural insecticides of the present invention can be achieved by treating them with the compound in a nursery facility, paddy field, field, seeds of fruit trees, vegetables, other crops, flowers, etc., paddy water, stems and leaves, or soil, etc., in accordance with the time of predicted pest emergence, before the emergence of pests or at the time when their emergence is confirmed. Among these, a preferred application mode is application utilizing the so-called systemic translocation property, in which the compound of the present invention is applied to the seedling soil of crops, flowers, etc., the soil in the planting hole at the time of transplanting, the base of the plant, irrigation water, cultivation water in hydroponic cultivation, etc., and is absorbed by the roots with or without the aid of soil.

[0142] The useful plants on which the pesticidal composition for agricultural and horticultural use of the present invention can be used are not particularly limited. Examples include cereals (e.g., rice, barley, wheat, rye, oats, corn, etc.), legumes (soybeans, adzuki beans, broad beans, green peas, kidney beans, peanuts, etc.), fruit trees and fruits (apples, citrus fruits, pears, grapes, peaches, plums, cherries, walnuts, chestnuts, almonds, bananas, etc.), leafy and fruit vegetables (cabbage, tomatoes, spinach, broccoli, lettuce, onions, leeks (Welsh onions, Japanese bunching onions), bell peppers, eggplants, strawberries, peppers, okra, chives, etc.), root vegetables (carrots, potatoes, sweet potatoes, taro, daikon radishes, turnips, lotus roots, burdocks, garlic, Chinese chives, etc.), industrial crops (cotton, hemp, sugar beets, hops, sugarcane, sugar beets, olives, rubber, coffee, tobacco, tea, etc.), cucurbits (pumpkins, cucumbers, watermelons, muskmelons, melons, etc.), forage grasses (orchard grass, sorghum, timothy, clover, alfalfa, etc.), turfgrasses (Korean lawn grass, bentgrass, etc.), ornamental crops such as spices (lavender, rosemary, thyme, parsley, pepper, ginger, etc.), flowers (chrysanthemums, roses, carnations, orchids, tulips, lilies, etc.), garden trees (ginkgo trees, cherry trees, oaks, etc.), forest trees (cedars, firs, pines, hiba arborvitae, Japanese cypresses, Japanese cedars, eucalyptus, etc.).

[0143] The above-mentioned "plants" also include plants that have been imparted with resistance to herbicides such as HPPD inhibitors such as isoxaflutole, ALS inhibitors such as imazethapyr and thifensulfuron-methyl, EPSP synthase inhibitors such as glyphosate, glutamine synthetase inhibitors such as glufosinate, acetyl-CoA carboxylase inhibitors such as sethoxydim, and herbicides such as bromoxynil, dicamba, and 2,4-D by classical breeding methods or genetic recombination techniques.

[0144] Examples of "plants" that have been conferred resistance through classical breeding methods include rapeseed, wheat, sunflower, and rice that are resistant to imidazolinone ALS-inhibiting herbicides such as imazethapyr, which are already sold under the trade name Clearfield®. Similarly, soybeans that have been conferred resistance to sulfonylurea ALS-inhibiting herbicides such as thifensulfuron-methyl through classical breeding methods are already sold under the trade name STS soybeans. Similarly, examples of plants that have been conferred resistance to acetyl-CoA carboxylase inhibitors such as trione oxime and aryloxyphenoxypropionic acid herbicides through classical breeding methods include SR corn. Plants that have been conferred resistance to acetyl-CoA carboxylase inhibitors are described in Proceedings of the National Academy of Sciences of the United States of America (Proc. Natl. Acad. Sci. USA), Vol. 87, pp. 7175-7179 (1990), etc. Furthermore, mutant acetyl-CoA carboxylases resistant to acetyl-CoA carboxylase inhibitors have been reported in Weed Science, Vol. 53, pp. 728-746 (2005), for example. Plants resistant to acetyl-CoA carboxylase inhibitors can be produced by introducing such mutant acetyl-CoA carboxylase genes into plants by genetic engineering or by introducing resistance-conferring mutations into plant acetyl-CoA carboxylase. Furthermore, plants resistant to acetyl-CoA carboxylase inhibitors, ALS inhibitors, and the like can be produced by introducing a nucleic acid with a base substitution mutation, as typified by chimeraplasty technology (Gura T. 1999. Repairing the Genome's Spelling Mistakes. Science 285: 316-318.), into plant cells to introduce site-specific amino acid substitution mutations into the plant acetyl-CoA carboxylase gene, ALS gene, or the like. The agricultural and horticultural insecticide of the present invention can also be used on these plants.

[0145] Furthermore, as toxins expressed in genetically modified plants, there are insecticidal proteins derived from Bacillus cereus and Bacillus popilliae; δ-endotoxins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C derived from Bacillus thuringiensis, insecticidal proteins such as VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins derived from nematodes; toxins produced by animals such as scorpion toxin, spider toxin, bee toxin or insect-specific neurotoxin; mycotoxins; plant lectins; agglutinins; protease inhibitors such as trypsin inhibitor, serine protease inhibitor, patatin, cystatin, papain inhibitor; ribosome-inactivating proteins (RIP) such as ricin, maize-RIP, abrin, luffin, saporin, bryodin; steroid metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glucosyltransferase, cholesterol oxidase; ecdyson inhibitors; HMG-CoA reductase; ion channel inhibitors such as sodium channel, calcium channel inhibitors; juvenile hormone esterase; diuretic hormone receptor; stilbene synthase; bibenzyl synthase; chitinase; glucanase and the like.

[0146] Also, as toxins expressed in such genetically modified plants, there are included δ-endotoxin proteins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9C, Cry34Ab or Cry35Ab, hybrid toxins of insecticidal proteins such as VIP1, VIP2, VIP3 or VIP3A, toxins with some parts deleted, and modified toxins. Hybrid toxins are created by new combinations of different domains of these proteins using recombinant techniques. As a toxin with some parts deleted, Cry1Ab with a part of the amino acid sequence deleted is known. As a modified toxin, one or more of the amino acids of the natural toxin are substituted. Examples of these toxins and recombinant plants capable of synthesizing them 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.

[0147] The toxins contained in these recombinant plants confer resistance to Coleoptera, Hemiptera, Diptera, Lepidoptera, and nematodes, among others. The agricultural and horticultural insecticide of the present invention can be used in combination with or as a systemic combination with these technologies.

[0148] The agricultural and horticultural insecticide of the present invention may be applied to plants where pests or nematodes are expected to occur, either directly or after appropriate dilution or suspension with water, in an amount effective for controlling the pests or nematodes. For example, for pests and nematodes that occur in fruit trees, grains, vegetables, etc., it can be sprayed on the stems and leaves, or it can be used by soaking seeds in the insecticide, seed dressing, seed treatment such as calper treatment, incorporation into the entire soil layer, row application, incorporation into bed soil, treatment with cell seedlings, treatment in planting holes, treatment at the base of plants, top dressing, treatment in rice boxes, application on the surface of water, or by application to soil and absorption through the roots. In addition, it can be applied to nutrient solutions in nutrient solution (hydroponic) cultivation, by fumigation, trunk injection, etc. Furthermore, the agricultural and horticultural insecticide of the present invention may be applied as is, or after being appropriately diluted or suspended in water or the like, in an amount effective for pest control in a location where the occurrence of the pest is predicted. For example, it may be sprayed against stored grain 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.

[0149] Examples of seed treatment methods include a method in which seeds are soaked in a liquid or solid formulation, 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 coated onto the seed surface; a method in which the formulation is mixed with an adhesive carrier such as a resin or polymer and then coated onto the seeds; and a method in which the formulation is sprayed around the seeds at the same time as planting. The "seeds" for which the seed treatment is carried out mean the initial-stage plants used for plant propagation. For example, in addition to seeds, bulbs, tubers, seed potatoes, bulbils, fruits, bulbs, or vegetative propagation plants for cuttage cultivation can be mentioned. The "soil" or "cultivation carrier" of plants when implementing the usage method of the present invention refers to a support for cultivating crops, particularly a support for growing roots. The material is not particularly limited as long as it is a material on which plants can grow, and it can be so-called soil, a seedling-raising mat, water, etc. Specific materials can be, for example, sand, pumice, vermiculite, diatomaceous earth, agar, gel substances, polymer substances, rock wool, glass wool, wood chips, bark, etc.

[0150] As a spraying method for crop foliage or stored-grain pests, household pests, sanitary pests, forest pests, etc., there are methods such as appropriately diluting liquid formulations such as emulsions and flowable agents or solid formulations such as wettable powders and granular wettable powders with water and spraying them, a method of spraying powders, or fumigation, etc. As a method of applying to soil, for example, a method of applying a liquid formulation to the base of the plant body or a seedling-raising seedbed, etc. with or without diluting it with water, a method of spraying granules to the base of the plant body or a seedbed for seedling raising, etc., a method of spraying powders, wettable powders, granular wettable powders, granules, etc. before sowing or before transplantation and mixing them with the whole soil, a method of spraying powders, wettable powders, granular wettable powders, granules, etc. into planting holes, furrows, etc. before sowing or before planting the plant body, etc.

[0151] As a method of applying to a rice seedling box, the dosage form may vary depending on the application time, such as application at sowing time, greening stage, transplantation time, etc. in some cases, but it may be applied in dosage forms such as powders, granular wettable powders, granules, etc. It can also be applied by mixing with the culture soil, and mixing of the culture soil with powders, granular wettable powders or granules, etc. can be carried out, for example, mixing with the bed soil, covering soil, mixing with the whole culture soil, etc. Simply applying the culture soil and various formulations alternately in layers may also be possible. As application methods for paddy fields, solid preparations such as jumbo agents, pack agents, granular agents, and granule wettable powders, and liquid preparations such as flowables and emulsions are usually sprayed on paddy fields in a flooded state. In addition, at the time of transplanting rice seedlings, an appropriate preparation can be directly applied, or mixed with fertilizers and then sprayed or injected into the soil. Also, by using a chemical solution such as an emulsion or a flowable at the water inlet to the paddy field such as a water inlet or an irrigation device, it is possible to apply the agent labor-savingly along with the supply of water.

[0152] In field crops, during the period from sowing to seedling raising, treatment can be carried out on the cultivation carrier or the like close to the seeds or plants. In plants directly sown in the field, in addition to direct treatment of the seeds, treatment of the base of the plants during cultivation is preferable. Spraying treatment using a granular agent or perfusion treatment of a chemical agent diluted or undiluted in water in a liquid state can be carried out. It is also a preferable treatment to mix the granular agent with the cultivation carrier before sowing and then sow. As treatment during the sowing and seedling raising period of cultivated plants to be transplanted, in addition to direct treatment of the seeds, perfusion treatment of a chemical agent in a liquid state or spraying treatment of a granular agent on the seedling bed for raising seedlings is preferable. Also, at the time of planting, it is also a preferable treatment to treat the planting holes with a granular agent or mix it with the cultivation carrier in the vicinity of the transplanting location. The agricultural and horticultural insecticide of the present invention is generally formulated into a convenient shape for use according to the conventional methods in pesticide formulations. That is, the compound represented by the general formula (1) of the present invention or its salts can be formulated into an appropriate dosage form, such as a suspension, an emulsion, a solution, a wettable powder, a granule wettable powder, a granular agent, a powder, a tablet, a pack agent, etc., by dissolving, separating, suspending, mixing, impregnating, adsorbing or adhering them to an appropriate inert carrier or, if necessary, together with an adjuvant in an appropriate ratio.

[0153] The composition of the present invention (an agricultural and horticultural insecticide or an animal parasite control agent) can contain, in addition to the active ingredient, additive components usually used in agricultural chemical formulations or animal parasite control agents as necessary. Examples of such additive components include carriers such as solid carriers and liquid carriers, surfactants, dispersants, wetting agents, binders, adhesion imparting agents, thickeners, coloring agents, spreading agents, sticking agents, antifreezing agents, anti-caking agents, disintegrants, anti-decomposition agents, etc. Other additives such as preservatives and plant pieces may be used as additive components as necessary. These additive components may be used alone or in combination of two or more kinds.

[0154] Examples of the solid carrier include natural minerals such as quartz, clay, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, diatomaceous earth, inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate, potassium chloride, organic solid carriers such as synthetic silicic acid, synthetic silicate, starch, cellulose, plant powder (e.g., sawdust, coconut shell, corn cob, tobacco stem, etc.), plastic carriers such as polyethylene, polypropylene, 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 kinds.

[0155] Examples of the liquid carrier include alcohols such as monohydric alcohols like methanol, ethanol, propanol, isopropanol, butanol, and polyhydric alcohols like ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, glycerin; polyhydric alcohol compounds such as propylene glycol ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone; ethers such as ethyl ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether, THF; aliphatic hydrocarbons such as normal paraffin, naphthene, isoparaffin, kerosene, mineral oil; aromatic hydrocarbons such as benzene, toluene, xylene, solvent naphtha, alkyl naphthalene; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride; esters such as ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate, dimethyl adipate; lactones such as γ-butyrolactone; amides such as dimethylformamide, diethylformamide, dimethylacetamide, N-alkylpyrrolidinone; nitriles such as acetonitrile; sulfur compounds such as dimethyl sulfoxide; vegetable oils such as soybean oil, rapeseed oil, cottonseed oil, castor oil; water, etc. These may be used alone or in combination of two or more kinds.

[0156] 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 alkyl sulfates, polyoxyethylene alkyl ether sulfates, polyoxyethylene alkyl phenyl ether sulfates, polyoxyethylene styryl phenyl ether sulfates, alkylbenzenesulfonates, alkylarylsulfonates, ligninsulfonates, alkylsulfosuccinates, naphthalenesulfonates, alkylnaphthalenesulfonates, salts of formalin condensates of naphthalenesulfonic acid, salts of formalin condensates of alkylnaphthalenesulfonic acid, fatty acid salts, polycarboxylates, polyacrylates, N-methyl-fatty acid sarcosinates, resinates, polyoxyethylene alkyl ether phosphates, polyoxyethylene alkylphenyl ether phosphates; cationic surfactants such as alkylamine salts such as laurylamine hydrochloride, stearylamine hydrochloride, oleylamine hydrochloride, stearylamine acetate, stearylaminopropylamine acetate, alkyltrimethylammonium chloride, and alkyldimethylbenzalkonium chloride;Examples include amphoteric surfactants such as amino acid type or betaine type. These surfactants may be used alone or in combination of two or more kinds.

[0157] Examples of the binder and the tackifier include carboxymethyl cellulose and its salts, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinylpyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, polyethylene glycol with an average molecular weight of 6,000 to 20,000, polyethylene oxide with an average molecular weight of 100,000 to 5,000,000, phospholipids (such as cephalin, lecithin, etc.), cellulose powder, dextrin, modified starch, polyaminocarboxylic acid chelate compound, crosslinked polyvinylpyrrolidone, copolymer of maleic acid and styrenes, (meth)acrylic acid copolymer, half ester of polymer composed of polyhydric alcohol and dicarboxylic anhydride, water-soluble salt of polystyrene sulfonic acid, paraffin, terpene, polyamide resin, polyacrylate, polyoxyethylene, wax, polyvinyl alkyl ether, alkylphenol formalin condensate, synthetic resin emulsion, etc.

[0158] Examples of the thickener include xanthan gum, guar gum, diutan gum, carboxymethyl cellulose, polyvinylpyrrolidone, carboxyvinyl polymer, acrylic polymer, starch compound, water-soluble polymer such as polysaccharide, high-purity bentonite, inorganic fine powder such as fumed silica (white carbon), etc.

[0159] Examples of the colorant include inorganic pigments such as iron oxide, titanium oxide, Prussian blue, and organic dyes such as alizarin dye, azo dye, metal phthalocyanine dye, etc.

[0160] Examples of the antifreezing agent include polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, glycerin, etc.

[0161] Examples of adjuvants for preventing caking or promoting disintegration include starch, alginic acid, polysaccharides such as 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.

[0162] Examples of anti-decomposition agents include desiccants 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.

[0163] Examples of preservatives include potassium sorbate and 1,2-benzothiazolin-3-one. Furthermore, other adjuvants 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 needed.

[0164] The blending ratio of the active ingredient compound can be adjusted as needed, and may be appropriately selected from the range of 0.01 to 90 parts by weight per 100 parts by weight of the agricultural and horticultural insecticide of the present invention. For example, when used as a dust, granule, emulsifiable concentrate, or wettable powder, the appropriate blending ratio is 0.01 to 50 parts by weight (0.01 to 50% by weight based on the total weight of the agricultural and horticultural insecticide).

[0165] 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, application method, application location, application time, etc., but may be appropriately selected depending on the purpose from a range of 0.001 g to 10 kg, preferably 0.01 g to 1 kg, of the active ingredient compound per 10 ares. The pesticidal composition for agricultural and horticultural use of the present invention can also be used in mixture with other pesticidal compositions for agricultural and horticultural use, acaricides, nematocides, fungicides, biological pesticides, etc. for the purpose of expanding the target pests and diseases to be controlled, the appropriate control period, or reducing the dosage. Further, it can also be used in mixture with herbicides, plant growth regulators, fertilizers, etc. according to the application scenarios.

[0166] Other agricultural and horticultural insecticides, acaricides, and nematicides used for such purposes include, for example, 3,5-xylyl methylcarbamate (XMC), fenobucarb (BPMC), Bt toxin-based insecticides, chlorfenson (CPCBS), dichlorodiisopropyl ether (DCIP), 1,3-dichloropropene (DD), 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, imidac1oprid, imiprothrin, indazapyroxamet, indoxacarb, esfenvalerate, ethiofencarb, ethion, ethiprole, etoxazole, ethofenprox, ethoprophos, etrimfos, emamectin, emamectin-benzoate, endosulfan, empenthrin, oxazosulfyl, oxamyl, oxydemeton-methyl, oxydeprofos: ESP, oxibendazole, oxfendazole, Potassium oleate, sodium oleate, cadusafos, kappa-bifenthrin, cartap, carbary1, carbosulfan, carbofuran, gamma-cyhalothrin, xylylcarb, quinalphos, kinoprene, chinomethionat, cloethocarb, clothianidin, clofentezine, chromafenozide, chlorantraniliprole, chlorethoxyfos,Chlordimeform, chlordane, chlorpyrifos, chlorpyrifos-methyl, chlorphenapyr, chlorfenson, chlorfenvinphos, chlorfluazuron, chlorobenzilate, chlorobenzoate, chloroprallethrin, Kelthane (dicofol), salithion, cyhalodiamide, cyanophos (CYAP), diafenthiuron, diamidafos, cyantraniliprole, theta-cypermethrin, dienochlor, cyetpyrafen, cyenopyrafen, dioxabenzofos, diofenolan, sigma-cypermethrin, cyclaniliprole, dichlofenthion (ECP), cycloprothrin, dichlorvos (DDVP), dicloromezotiaz, disulfoton, dinotefuran, cyhalodiamide, cyhalothrin, cyphenothrin, cyfluthrin, diflubenzuron, cyflumetofen, diflovidazin, cyproflanilide, cyhexatin, cypermethrinDimethylvinphos, dimethoate, dimpropyridaz, dimefluthrin, silafluofen, cyromazine, spidoxamat, spinetoram, spinosad, spirobudifen, spirodiclofen, spirotetramat, spiropidione, spiromesifen fen, sulfluramid, sulprofos, sulfoxaflor, zeta-cypermethrin, diazinon, tau-fluvalinate, dazomet, thiacloprid, thiamethoxam, tioxazafen, thiodicarb iodicarb), thiocyclam, thiosultap, thiosultap sodium, thionazin, thiometon, thiolanthraniliprole, DEET, dieldrin, tetrachlorantraniliprole, cyclopyrazoflor, tetrachlorvinphos, tetradifon, tetraniliprole, tetramethylfluthrin, tetramethrin, tebupirimfos, tebufenozide, tebufenpyrad, tefluthrin,Teflubenzuron, Demeton-S-methyl, Temephos, Deltamethrin, Terbufos, Doramectin, Tralopyril, Tralomethrin, Transfluthrin, Triazamate, Triazuron, Trichlamide, Trichlorphon (DEP), Triflumezopyrium, Trifluenfuronate, Triflumuron, Tolfenpyrad, Naled (BRP), Nicofluprole, Nithiazine, Nitenpyram, Novaluron, Noviflumuron, Hydroprene, Vaniliprole, Vamidothion, Parathion, Parathion-methyl, Halfenprox, Halofenozide, Bistrifluron, Bisultap, Hydramethylnon, Hydroxypropyl starch, Binapacryl, Pyflubumide, Bifenazate, Bifenthrin, Pymetrozine, Pyraclorfos, Pyrafluprole, Pyridafenthion, Pyridaben, Pyridalyl, Pyrifluquinazon, Pyriprole,Pyriproxyfen, pirimicarb, pyrimidifen, pyriminostrobin, pirimiphos-methyl, pyrethrins, fipronil, fenazaquin, fenamiphos, phenisobromorate, fenitrothion (MEP), fenoxycarb, fenothiocarb, fenothrin, fenobucarb, fensulfothion, fenthion (MPP), phenthoate PAP), fenvalerate, fenpyroximate, fenpropathrin, fenbendazole, fenmezoditiaz, fosthiazate, formetanate, butathiofos , buprofezin, furathiocarb, prallethrin, fluacrypyrim, furazaindolizine, fluazinam, fluazuron, fluensulfone, fluxametamide, fluchlordiniliprole, flucycloxuron, flucythrinate, fluvalinate, flupyradifurone, flupyroxystrobin, flufiprole, flupyradifurone,flupyrazofos, flupyrimin, flufenerim, flufenoxystrobin, flufenoxuron, flufenzine, flufenoprox, fluproxyfen, flubrocythrinate, fluhexafon, flubendiamide, flupentiofenox, flumethrin, flurimfen, prothiofos, protrifenbute, flonicamid, propaphos, propargite (BPPS), profenofos, broflanilide, profluthrin, propoxur (PHC), flometoquin, alpha - bromadiolone, bromopropylate, beta - cyfluthrin, hexaflumuron, hexythiazox, heptafluthrin, heptenophos, permethrin, benclothiaz, bendiocarb, benzpyrimoxan, bensu1tap, 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, methoxa, Examples thereof include diazone (metoxadiazone), methoxychlor, methoxyfenozide, metofluthrin, methoprene, metolcarb, meperfluthrin, mevinphos, monocrotophos, monosultap, momfluorothrin, lambda-cyhalothrin, ryanodine, lufenuron, rescalure, resmethrin, lepimectin, rotenone, levamisol hydrochloride, fenbutatin oxide, morantel tartarate, methyl bromide, cyhexatin, calcium cyanamide, calcium polysulfide, sulfur, and nicotine-sulfate, etc.

[0167] For example, as agricultural and horticultural fungicides used for the same purpose, there are aureofungin, azaconazole, azithiram, acypetacs, acibenzolar, acibenzolar-S-methyl, azoxystrobin, anilazine, amisulbrom, ampropylfos, ametoctradin, allyl alcohol, aldimorph, amobam, isotianil, isovaledione, isopyrazam, isofetamid, isoflucypram, isoprothiolane, ipconazole, ipfentrifluconazole, ipflufenoquin, iprodione, iprovalicarb, iprobenfos, imazalil, iminoctadine, metam, iminoctadine-albesilate, iminoctadine-triacetate, imibenconazole, inpyrfluxam, uniconazole, uniconazole-P, echlomezole, edifenphos, etaconazole, ethaboxam, ethirimol, etem, ethoxyquin, etridiazole, enestroburin,enoxastrobin, epoxiconazole, oxadixyl, oxathiapiprolin, oxycarboxin, copper-8-quinolinolate, oxytetracycline, copper-oxinate, oxpoconazole, oxpoconazole-fumarate, oxolinic acid, octhilinone, ofurace, orysastrobin, carbam (metam-sodium), kasugamycin, carbamorph, carpropamid, carbendazim, carboxin, carvone, quinazamid, quinacetol, quinoxyfen, quinofumelin, chinomethionat (quinomethionate), captafol, captan, kiralaxyl, quinconazole, quintozene, guazatine, cufraneb, cuprobam, coumoxystrobin, glyodin, griseofulvin, climbazole, cresol, kresoxim-methyl, chlozolinate, clotrimazole, chlobenthiazone, chloraniformethan, chloranilChlorquinox, Chloropicrin, Chlorfenazole, Chloroinconazide, Chlorodinitronaphthalene, Chlorothalonil, Chloroneb, Salicylanilide, Zarilamid, Cyazofamid, Diethyl Pyrocarbonate, Diethofencarb, Cyclafuramid, Diclocymet, Dichlozoline, Diclobutrazol, Cyclobutrifluram, Dichlofluanid, Cycloheximide, Dichlobentiazox, Diclomezine, Dicloran, Dichlorophen, Dichlone, Disulfiram, Ditalimfos, Dithianon, Diniconazole, Diniconazole-M, Zineb, Dinocap, Dinocton, Dinosulfon, Dinoterbon, Dinobuton, Dinopenton, Dipymetitrone, Dipyrithione, Diphenylamine, Difenoconazole, Cyflufenamid, Diflumetorim, Cyproconazole, Cyprodinil, CyprofuramCipendazole, simeconazole, dimethirimol, dimethomorph, cymoxanil, dimoxystrobin, ziram, silthiofam, streptomycin, spiroxamine, sultropen, sedaxane, zoxamide, dazomet, thiadiazine, tiadinil, thiadifluor, Thiabendazole, tioximid, thiochlorfenphim, thiophanate, thiophanate-methyl, thifluzamide, thicyofen, thioquinox, thiram, decafentin, 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, pyrapropoin, pyrametostrobin, pyriophenone, pyridinitril, pyridiflumetofen,Pyrisoxazole, pyridaclomethyl, 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, furam Topil (furametpyr), furalaxyl (furalaxyl), fluacrypyrim (fluacrypyrim), fluazinam (fluazinam), fluindapyr (fluindapyr), fluoxastrobin (fluoxastrobin), fluoxapiprolin (fluoxapiprolin), fluoxytioconazole (fluoxytioconazole), fluotrimazole (fluotrimazole), fluopicolide (fluopicolide), fluopimomide (Fluopimomide),Fluopyram, fluoroimide, furcarbanil, fluxapyroxad, fluquinconazole, fluconazole, furconazole-cis, fludioxonil, flusilazole, flusulfamide, flutianil, flu Flutolanil, flutriafol, flufenoxadiazam, flufenoxystrobin, furfural, flubeneteram, furmecyclox, flumethylsulfonim, 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, benzobindifluphyl (b, enzovindiflupyr), bentaluron, benthiazole, benthiavalicarb, benthiavalicarb-isopropyl, penthiopyrad, penflufen, boscalid, phosdiphen, fosetyl, fosetyl-Al, polyoxins, polyoxorim, polycarbamate, folpet, formaldehyde, machine oil, maneb, mancozeb, mandipropamid, mandestrobin, myclozolin, myclobutanil, mildiomycin, milneb, mecarbinzid, methasulfocarb, metazoxolon, metam, metam-sodium, metalaxyl, metalaxyl-M, metarylpicoxamid, metiram, methyl isothiocyanate (methylisothiocyanate), meptyldinocap, methyltetraprole, metconazole, metsulfovax, methfuroxam, metominostrobin, metrafenone, mepanipyrim, mefenoxam, mefentrifluconazole, meptyldinocap, mepronil, mebenil, iodomethane, rabenzazole, methyl bromide, benzalkonium chloride, basic copper chloride, basic copper sulfate, inorganic fungicides such as metallic silver, sodium hypochlorote, cupric hydroxide, wettable sulfur, calcium polysulfide, potassium hydrogen carbonate, sodium hydrogen carbonate, sulfur, copper sulfate anhydride, nickel dimethyldithiocarbamate, copper-based compounds such as oxine copper, zinc sulfate, copper sulfate pentahydrate, etc. can be exemplified.

[0168] Similarly, as herbicides, for example, 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, acifluorfen, aziprotryne, azimsulfuron, asulam, acetochlor, atrazine, atraton, anisuron, anilofos, aviglycine, abscisic acid, amicarbazone, amidosulfuron, amitrole, aminocyclopyrachlor, aminopyralid, amibuzin, amiprophos-methyl, ametridione, ametryn, alachlor, allidochlor, alloxydim, alorac, iofensulfuron, isouron, isocarbamid, isoxachlortole, isoxapyrifop, isoxaflutole, isoxaben, isocil, isonoruron, isoproturon, isopropalin, isopolinate, isomethiozin, inabenfide, ipazine,Iptriazopyrid, ipfencarbazone, iprymidam, imazaquin, imazapic, imazapyr, imazamethapyr, imazamethabenz, imazamethabenz-methyl, imazamox, imazethapyr, imazosulfuron, indaziflam, indanofan, indolebutyric acid, indolauxipyr, indolauxipyr-cyanomethyl, uniconazole-P, eglinazine, esprocarb, ethametsulfuron, ethametsulfuron-methyl, ethalfluralin, ethiolate, ethychlozate-ethyl, ethidimuron, etinofen, ethephon, ethoxysulfuron, ethoxyfen, etnipromid, ethofumesate, etobenzanid, epyrifenacil, epronaz, erbon, endothal, oxadiazon, oxadiargyl, oxaziclomefone, oxasulfuron, oxapyrazon, oxyfluorfen, oryzalinorthosulfamuron, orbencarb, cafenstrole, cambendichlor, carbasulam, carfentrazone, carfentrazone-ethyl, karbutilate, carbetamide, carboxazole, quizalofop zalofop, quizalofop-P, quizalofop-ethyl, xylachlor, quinoclamine, quinonamid, quinclorac, quinmerac, cumyluron, clacyfos, cliodinate, glyphosate, glufosinate ), glufosinate-P, credazine, clethodim, cloxyfonac, clodinafop, clodinafop-propargyl, clotoluron, clopyralid, cloproxydim, cloprop, clobromuron, clofop 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, dichlorprop, dichlorprop-P, dichlobenil, diclofop, diclofop-methyl, dichlormate, dichloralurea, diquat, cisanilide, disul, siduron, dithiopyrDinitramine, cinidon-ethyl, dinosam, cinosulfuron, dinoseb, dinoterb, dinofenate, dinoprop, cyhalofop-butyl, cypyrafluone, diphenamid, difenoxuron, difenopentene Openten, difenzoquat, sibutryne, cyprazine, cyprazole, diflufenican, diflufenzopyr, dipropetryn, cypromid, cyperquat, gibberellin, simazine, dimexano, dimesulfazet sulfazet, dimethachlor, dimidazon, dimethametryn, dimethenamid, simetryn, simeton, dimepiperate, dimefuron, cinmethylin, swep, sulglycapin, sulcotrione, sulfarate te), sulfentrazone, sulfosulfuron, sulfometuron, sulfometuron-methyl, secbumeton, sethoxydim, sebuthylazine, terbacil, daimuron, dazomet, dalapon, thiazafluron,thiazopyr, tiafenacil, thiencarbazone, thiencarbazone-methyl, tiocarbazil, tioclorim, thiobencarb, thidiazimin, thidiazuron, thifensulfuron, thifensulfuron-methyl, desmedipham, desmetryn, tetflupyrolimet, tetrafluron, thenylchlor, tebutam, tebuthiuron, terbumeton, tepraloxydim, tefuryltrione, tembotrione, delachlor, terbacil, terbucarb, terbuchlor, terbuthylazine, terbutryn, topramezone, tralkoxydim, triaziflam, triasulfuron, triafamone, tri-allate, trietazine, tricamba, triclopyr, tridiphane, tritac, tritosulfuron, tripyrasulfone, trifludimoxazin, triflusulfuron, triflusulfuron-methyl, trifluralinTrifloxysulfuron, Tripropindan, Tribenuron, Tribenuron-methyl, Trifop, Trifopsime, Trimeturon, Tolpyralate, Naptalam, Naproanilide, Napropamide, Nicosulfuron, Nitralin, Nitrofen, Nitrofluorfen, Nipyraclofen, Neburon, Norflurazon, Noruron, Barban, Paclobutrazol, Paraquat, Parafluron, Haloxydine, Halauxifen, Haloxyfop, Haloxyfop-P, Haloxyfop-methyl, Halosafen, Halosulfuron, Halosulfuron-methyl, Bilanafos, Bixlozone, Picloram, Picolinafen, Bicyclopyrone, Bispyribac, Bispyribac-sodium, Pydanon, Pinoxaden, Bipyrazone, Bifenox, Piperophos, Hymexazol, Pyraclonil, Pyrasulfotole, Pyrazoxyfen, PyrazosulfuronPyrazosulfuron-ethyl, pyrazolate, bilanafos, pyraflufen, pyraflufen-ethyl, p, yraflufen-ethyl, pyriclor, pyridafol, pyrithiobac, pyrithiobac-sodium, pyridate, pyriftalid, pyributicarb, pyriflubenzoxim, pyribenzoxim, pyrimisulfan, pyrimisulfuron rimisulfuron, pyriminobac-methyl, pyroxasulfone, pyroxsulam, fenasulam, phenisopham, fenuron, fenoxasulfone, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-methyl, Phenothiol, fenoprop, phenobenzuron, fenquinotrione, fentiaprop, fenteracol, fentrazamide, fenpyrazone, phenmedipham, phenmedipham-ethyl, butachlor r), butafenacil, butamifos, buthiuron, buthidazole, butyrate, buturon, butenachlor, butroxydim, butralin, butroxydim, flazasulfuron, flamprop, furyloxyfen,Prynachlor, primisulfuron-methyl, fluazifop, fluazifop-P, fluazifop-butyl, fluazolate, fluroxypyr, fluothiuron, fluometuron, fluoroglycofen, flurochloridone, fluorodifen, fluoronitrofen, fluoromidine, flucarbazone, flucarbazone-sodium, fluchloraminopyr, fluchloraminopyr-tefuryl, fluchloralin, flucetosulfuron, fluthiacet, fluthiacet-methyl, flusulfinam, flupyrsulfuron, flufenacet, flufenican, flufenoximacil, flufenpyr, flupropacil, flupropanate, flupoxam, flumioxazin, flumiclorac, flumiclorac-pentyl, flumipropyn, flumezin, fluometuron, flumetsulam, fluridone, flurtamone, fluroxypyr, pretilachlorProxan, proglinadin, broclozone, procyazine, prodiamine, prosulfalin, prosulfuron, prosulfocarb, propaquizafop, propachlor, propazine, propanil, propyzamide yzamide, propisochlor, prohydrojasmon, propyrisulfuron, propham, profluazol, profluralin, prohexadione-calcium, propoxycarbazone, propoxycarbazone-sodium m), profoxydim, bromacil, brompyrazone, prometryn, prometon, bromoxynil, bromofenoxim, bromobutide, bromobonil, florasulam, florpyrauxifen, hexachloroacetone etone), hexazinone, petoxamid, benazolin, penoxsulam, pebulate, beflubutamid, beflubutamid-M, vernolate, perfluidone, bencarbazone, benquitrione, benzadox,benzipram, benzylaminopurine, benzthiazuron, benzfendizone, bensulide, bensulfuron-methyl, benzoylprop, benzobicyclon, benzofenap, benzofluor, bentazone, pentanochlor, benthiocarb, pendimethalin, pentoxazone, benfluralin, benfuresate, fosamine, fomesafen, foramsulfuron, forchlorfenuron, maleic hydrazide, mecoprop, mecoprop-P, medinoterb, mesosulfuron, mesosulfuron-methyl, mesotrione, mesoprazine, methoprotryne, metazachlor, methazole, metazosulfuron, methabenzthiazuron, metamitron, metamifop, metam, metalpropalin, methiuron, methiozolin, methiobencarb, methyldymron, metoxuron, metosulam, metsulfuronExamples thereof include metsulfuron-methyl, metflurazon, metobromuron, metobenzuron, methometon, metolachlor, metribuzin, mepiquat-chloride, mefenacet, mefluidide, monalide, monisouron, monuron, monochloroacetic acid, monolinuron, molinate, morfamquat, iodosulfuron, iodosulfuron-methyl-sodium, iodobonil, iodomethane, lactofen, lancotrione, linuron, rimisoxafen, rimsulfuron, lenacil, rhodethanil, calcium peroxide, methyl bromide, etc.

[0169] 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 nematicides such as Monacrosporium phymatophagum, Steinernema carpocapsae, Steinernema kushidai, and Pasteuria penetrans; and microbial 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 radiobactor, non-pathogenic Erwinia carotovora, and Bacillus subtilis, or biological pesticides used as herbicides, such as Xanthomonas campestris.

[0170] Furthermore, as biological pesticides, for example, natural enemy organisms such as Encarsia formosa, Aphidius colemani, Aphidoletes aphidimyza, Diglyphus isaea, Dacnusa sibirica, Phytoseiulus persimilis, Amblyseius cucumeris, Orius sauteri, microbial pesticides such as Beauveria brongniartii, (Z)-10-tetradecenyl acetate, (E,Z)-4,10-tetradecadienyl acetate, (Z)-8-dodecenyl acetate, (Z)-11-tetradecenyl acetate, (Z)-13-eicosen-10-one, 14-methyl-1-octadecene and other pheromone agents can also be used in combination.

Example

[0171] Typical examples of the present invention are illustrated below, but the present invention is not limited thereto.

[0172] Production Example 1 Production of 4-((4-fluorophenyl)carbamoyl)-3-hydroxy-1-phenylpyridazin-1-ium-5-oleate (Compound No. 1-1)

Chemical formula

[0173] 4-(Ethoxycarbonyl)-3-hydroxy-1-phenylpyridazin-1-ium-5-olate (0.19 g, 0.73 mmol), 4-fluoroaniline (0.097 g, 0.87 mmol), and toluene (5.0 mL) were stirred under heating to reflux for 1.5 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and the precipitated crystals were washed with methyl tert-butyl ether to obtain 4-((4-fluorophenyl)carbamoyl)-3-hydroxy-1-phenylpyridazin-1-ium-5-olate (0.030 g, 0.092 mmol). Yield: 13% Physical properties: Melting point 240 °C

[0174] Production Example 2 Production of 4-(tert-butylcarbamoyl)-3-hydroxy-1-(6-(trifluoromethyl)pyridin-3-yl)pyridazin-1-ium-5-olate (Compound No. 1-106)

Chemical formula

[0175] Ethyl 5-hydroxy-3-oxo-1-(6-(trifluoromethyl)pyridin-3-yl)-1,2,3,6-tetrahydropyridazine-4-carboxylate (0.10 g, 0.30 mmol) was dissolved in toluene (5.0 mL), tert-butylamine (1.0 mL) was added, and the mixture was stirred at 135 °C for 1 hour. After completion of the reaction, the mixture was cooled to room temperature and concentrated under reduced pressure. Ethyl acetate and methyl tert-butyl ether were added to the obtained residue, and the precipitated solid was collected by filtration to obtain 4-(tert-butylcarbamoyl)-3-hydroxy-1-(6-(trifluoromethyl)pyridin-3-yl)pyridazin-1-ium-5-olate (78 mg, 0.22 mmol). Yield: 73% Physical properties: Melting point 177-180 °C

[0176] Production Example 3 Production of 1-(6-cyano-5-(methylsulfinyl)pyridin-3-yl)-4-((4-fluorophenyl)carbamoyl)-3-hydroxypyridazin-1-ium-5-olate (Compound No. 1-139)

Chem.

[0177] 1-(6-Cyano-5-(methylthio)pyridin-3-yl)-N-(4-fluorophenyl)-5-hydroxy-3-oxo-1,2,3,6-tetrahydropyridazine-4-carboxamide (0.10 g, 0.25 mmol) was dissolved in tetrahydrofuran (2 mL), methanol (2 mL), and water (2 mL), and Oxone® (0.34 g, 0.55 mmol) was added. The mixture was stirred at room temperature for 2 hours. Subsequently, methanol (4 mL) was added to dissolve the precipitated solid. The mixture was stirred overnight at room temperature, and the precipitated solid was collected by filtration and washed with methyl tert-butyl ether to obtain 1-(6-cyano-5-(methylsulfinyl)pyridin-3-yl)-4-((4-fluorophenyl)carbamoyl)-3-hydroxypyridazin-1-ium-5-olate (30 mg, 0.072 mmol). Yield: 29% Physical properties: Melting point 201 - 203 °C

[0178] Production Example 4 Production of 4-((4-fluorophenyl)carbamothioyl)-3-hydroxy-1-(6-(trifluoromethyl)pyridin-3-yl)pyridazin-1-ium-5-olate (Compound No. 1-89)

Chem.

[0179] N-(4-Fluorophenyl)-5-hydroxy-3-oxo-1-(6-(trifluoromethyl)pyridin-3-yl)-1,2,3,6-tetrahydropyridazine-4-carbothioamide (120 mg, 0.291 mmol) was dissolved in tetrahydrofuran (6 mL), and N,N-diisopropylethylamine (45.0 mg, 0.349 mmol) and tetra-n-butylammonium iodide (11.0 mg, 0.0291 mmol) were added, followed by stirring at room temperature for 5.5 hours. Then, the reaction solution was concentrated under reduced pressure and washed with tetrahydrofuran to obtain 4-((4-fluorophenyl)carbamothioyl)-3-hydroxy-1-(6-(trifluoromethyl)pyridin-3-yl)pyridazin-1-ium-5-olate (24.0 mg, 0.0585 mmol). Yield: 20% Physical properties: Melting point 298 - 300 °C

[0180] Production Example 5 Production of 4-((4-fluorophenyl)carbamoyl)-3-hydroxy-1-(6-(trifluoromethyl)pyridin-3-yl)pyridazin-1-ium-5-thiolate (Compound No. 2-1) [Chemical formula]

[0181] N-(4-Fluorophenyl)-5-mercapto-3-oxo-1-(6-(trifluoromethyl)pyridin-3-yl)-1,2,3,6-tetrahydropyridazine-4-carboxamide (62.1 mg, 0.151 mmol) was dissolved in tetrahydrofuran (3 mL), and N,N-diisopropylethylamine (23.4 mg, 0.181 mmol) and tetra-n-butylammonium iodide (5.6 mg, 0.0151 mmol) were added, followed by stirring at room temperature for 4 hours. Then, the reaction solution was concentrated under reduced pressure and washed with chloroform to obtain 4-((4-fluorophenyl)carbamoyl)-3-hydroxy-1-(6-(trifluoromethyl)pyridin-3-yl)pyridazin-1-ium-5-thiolate (3.2 mg, 0.00780 mmol). Yield: 5% Physical properties: 1 H-NMR (DMSO / TMS, ppm): δ 14.7 (s, 1H), 9.48 (s, 1H), 9.31 (s, 1H), 8.67 (d, 1H), 8.26 (d, 1H), 7.74 - 7.70 (m, 2H), 7.27 (t, 2H)

[0182] Production Example 6 Production of 4-((4-fluorophenyl)carbamoyl)-3-hydroxy-1-(6-(trifluoromethyl)pyridin-3-yl)pyridazin-1-ium-5-hydroxyamid (Compound No. 3-1)

Chemical formula

[0183] N-(4-Fluorophenyl)-5-hydroxy-3-oxo-1-(6-(trifluoromethyl)pyridin-3-yl)-1,2,3,6-tetrahydropyridazine-4-carboxamide (298 mg, 0.76 mmol) was dissolved in ethanol (4.0 mL). Hydroxylamine hydrochloride (169 mg, 2.28 mmol) and triethylamine (315 μL, 2.28 mmol) were added to the reaction solution, and the mixture was stirred at 70 °C for 6 hours. After completion of the reaction, the mixture was cooled to room temperature, 1N hydrochloric acid was added, and the mixture was extracted three times with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 4-((4-fluorophenyl)carbamoyl)-3-hydroxy-1-(6-(trifluoromethyl)pyridin-3-yl)pyridazin-1-ium-5-hydroxyamid (169 mg, 0.41 mmol). Yield: 54% Physical properties: Melting point 173 - 174 °C

[0184] Production Example 1 of Intermediate Production of 4-(ethoxycarbonyl)-3-hydroxy-1-phenylpyridazin-1-ium-5-oleate (Compound No. 4-1)

Chemical formula

[0185] Ethyl 3-(2-(2-ethoxy-2-oxoethyl)-2-phenylhydrazinyl)-3-oxopropanoate (1.6 g, 5.2 mmol) was dissolved in ultra-dehydrated ethanol (20 mL), and a 20% solution of sodium ethoxide in ethanol (3.5 g, 10 mmol) was added. The mixture was heated and stirred at 80°C for 1 hour. After the reaction was completed, the ethanol was removed by evaporation under reduced pressure, water (20 mL) was added, and the aqueous layer was washed with ethyl acetate. 3N hydrochloric acid (4 mL) was added to the resulting aqueous layer, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over anhydrous sodium sulfate, the solvent was removed by evaporation under reduced pressure, and the residue was washed with methyl tert-butyl ether to give 4-(ethoxycarbonyl)-3-hydroxy-1-phenylpyridazin-1-ium-5-olate (0.54 g, 2.1 mmol). Yield: 40% Physical properties: 1 H-NMR (CDCl3 / TMS, ppm): δ8.53(s,1H),7.31-7.26(m,5H),4.47(q,2H),1.40(t,3H)

[0186] Reference Example 1 Preparation of N-(4-fluorophenyl)-5-mercapto-3-oxo-1-(6-(trifluoromethyl)pyridin-3-yl)-1,2,3,6-tetrahydropyridazine-4-carboxamide Reference Example 1-1 Preparation of tert-butyl 5-((4-fluorophenyl)carbamoyl)-4-hydroxy-6-oxo-2-(6-(trifluoromethyl)pyridin-3-yl)-2,3-dihydropyridazine-1(6H)-carboxylate [ka]

[0187] Under ice-cooling, di-tert-butyl dicarbonate (1.2 g, 5.6 mmol) and N,N-dimethyl-4-aminopyridine (0.68 g, 5.6 mmol) were added to a chloroform (15 mL) solution of N-(4-fluorophenyl)-5-hydroxy-3-oxo-1-(6-(trifluoromethyl)pyridin-3-yl)-1,2,3,6-tetrahydropyridazine-4-carboxamide (2.0 g, 5.0 mmol), and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, an aqueous potassium hydrogen sulfate solution was added to the reaction mixture, and the mixture was extracted three times with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain tert-butyl 5-((4-fluorophenyl)carbamoyl)-4-hydroxy-6-oxo-2-(6-(trifluoromethyl)pyridin-3-yl)-2,3-dihydropyridazine-1(6H)-carboxylate (0.98 g, 1.9 mmol). Yield: 39% Physical properties: melting point 170 - 172 °C

[0188] Reference Example 1-2 Production of tert-butyl 5-((4-fluorophenyl)carbamoyl)-4-mercapto-6-oxo-2-(6-(trifluoromethyl)pyridin-3-yl)-2,3-dihydropyridazine-1(6H)-carboxylate

Chemical formula

[0189] A solution of tertiary butyl 5-((4-fluorophenyl)carbamoyl)-4-hydroxy-6-oxo-2-(6-(trifluoromethyl)pyridin-3-yl)-2,3-dihydropyridazine-1(6H)-carboxylate (420 mg, 0.847 mmol) in toluene (10 mL) was added with 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide (202 mg, 0.50 mmol), and heated to reflux for 2.5 hours. The reaction solution was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain tertiary butyl 5-((4-fluorophenyl)carbamoyl)-4-mercapto-6-oxo-2-(6-(trifluoromethyl)pyridin-3-yl)-2,3-dihydropyridazine-1(6H)-carboxylate (196 mg, 0.38 mmol). Yield: 45% Physical properties: melting point 164-165 °C

[0190] Reference Example 1-3 Preparation of N-(4-fluorophenyl)-5-mercapto-3-oxo-1-(6-(trifluoromethyl)pyridin-3-yl)-1,2,3,6-tetrahydropyridazine-4-carboxamide

Chemical formula

[0191] Tertiary butyl 5-((4-fluorophenyl)carbamoyl)-4-mercapto-6-oxo-2-(6-(trifluoromethyl)pyridin-3-yl)-2,3-dihydropyridazine-1(6H)-carboxylate (50.7 mg, 0.0996 mmol) was dissolved in trifluoroacetic acid (2 mL) and stirred at room temperature for 3 hours. Then, the reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to obtain N-(4-fluorophenyl)-5-mercapto-3-oxo-1-(6-(trifluoromethyl)pyridin-3-yl)-1,2,3,6-tetrahydropyridazine-4-carboxamide (7.6 mg, 0.0184 mmol). Yield: 19% Physical properties: Melting point 182-184℃

[0192] Formulation examples are shown below, but the present invention is not limited to these. In the formulation examples, parts are parts by weight.

[0193] Formulation example 1. Compound of the present invention 10 parts 70 parts xylene N-methylpyrrolidone 10 parts Polyoxyethylene nonylphenyl ether Mixture with calcium alkylbenzene sulfonate 10 parts The above ingredients are mixed and dissolved uniformly to form an emulsion.

[0194] Formulation example 2. Compound of the present invention 3 parts 82 parts clay powder 15 parts diatomaceous earth powder The above ingredients are mixed and pulverized uniformly to obtain a powder.

[0195] 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.

[0196] Formulation Example 4. Compound of the present invention 20 parts Kaolin and synthetic highly dispersed silica 75 parts Polyoxyethylene nonylphenyl ether Mixture with calcium alkylbenzene sulfonate 5 parts The above ingredients are uniformly mixed and pulverized to prepare a wettable powder.

[0197] Examples of biological tests are shown below, but the present invention is not limited to these.

[0198] 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 prepared by diluting a compound represented by general formula (1) of the present invention as an active ingredient to 50 ppm or 500 ppm, and after air drying, the seedlings were left to stand in a thermostatic chamber at 25°C. Six days after immersion in the chemical solution, the number of surviving insects was counted, and the corrected insect mortality rate was calculated using the following formula, and the results were evaluated according to the following criteria: 10 insects per plot, 3 replicates.

[0199]

number

[0200] Judgment criteria: A... Mortality rate 100% B... Mortality rate 99%~90% C... Mortality rate 89%~80% D... Mortality rate 79%~50% E... Mortality rate 49%~0%

[0201] As a result, among the compounds represented by general formula (1) of the present invention, compound numbers 1-3, 1-5, 1-6, 1-7, 1-8, 1-16, 1-17, 1-18, 1-19, 1-22, 1-39, 1-40, 1-46, 1-47, 1-49, 1-50, 1-53, 1-55, 1-56, 1-57, 1-58, 1-59, 1-60, 1-61, 1-62, 1-63, 1-64, 1-67, 1-69, 1-70, 1-72, 1‐74, 1‐75, 1‐76, 1‐77, 1‐81, 1‐82, 1‐83, 1‐84, 1‐87, 1‐88, 1‐89, 1‐91, 1‐92, 1‐97, 1‐100, 1‐101, 1‐103, 1‐112, 1‐113, 1‐115, 1‐118, 1‐121, 1‐122, 1‐124, 1‐126, 1‐128, 1‐129, 1‐130, 1‐131, 1‐132, 1‐133, 1‐134, 1‐135, 1‐136, Compounds 1-137, 1-138, 1-139, 1-145, 1-146, 1-147 and 2-1 showed activity of A rating at 500 ppm, and in particular, compounds 1-3, 1-5, 1-6, 1-16, 1-17, 1-18, 1-19, 1-22, 1-40, 1-46, 1-47, 1-49, 1-50, 1-53, 1-56, 1-57, 1-58, 1-59, 1-60, 1-61, 1-62, 1-63, 1-64, 1-67, 1-70 , 1-72, 1-74, 1-75, 1-76, 1-77, 1-81, 1-82, 1-83, 1-84, 1-87, 1-88, 1-89, 1-91, 1-103, 1-112, 1-115, 1-118, 1-121, 1-122, 1-128, 1-129, 1-130, 1-131, 1-132, 1-134, 1-136, 1-137, 1-145, 1-147 and 2-1 showed excellent activity at 50 ppm, rated A.

[0202] Test Example 2. Insecticidal test against the small brown planthopper (Laodelphax striatellus) The compound represented by the general formula (1) of the present invention or a salt thereof was dispersed in water and diluted to a chemical solution of 50 ppm or 500 ppm. Rice seedlings (variety: Nipponbare) were immersed in the chemical solution for 30 seconds, air-dried, placed in a glass test tube, inoculated with 10 larvae of Laodelphax striatellus at the third instar each, plugged with cotton, and the number of dead and alive insects was investigated 8 days after inoculation. The corrected mortality rate was calculated from the following formula and the determination was made according to the criteria of Test Example 1.

[0203]

Number

[0204] As a result, among the compounds represented by the general formula (1) of the present invention against Laodelphax striatellus, Compound Nos. 1-6, 1-7, 1-18, 1-19, 1-22, 1-30, 1-39, 1-40, 1-46, 1-47, 1-48, 1-50, 1-51, 1-52, 1-53, 1-55, 1-56, 1-58, 1-59, 1-61, 1-62, 1-63, 1-64, 1-67, 1-69, 1-70, 1-72, 1-75, 1-76, 1-77, 1-81, 1-82, 1-83, 1-84, 1-87, 1-88, 1-89, 1-91, 1-92, 1-95, 1-97, 1-100, 1-101, 1-103, 1-112, 1-113, 1-115, 1-121, 1-122, 1-123, 1-124, 1-126, 1-129, 1-130, 1-132, 1-134, 1-135, 1-136, 1-137, 1-138, 1-139, 1-147 and 2-1 showed activity of Grade A at 500 ppm. In particular, Compound Nos. 1-7, 1-18, 1-19, 1-22, 1-39, 1-46, 1-47, 1-50, 1-53, 1-55, 1-59, 1-62, 1-63, 1-64, 1-67, 1-69, 1-70, 1-72, 1-75, 1-76, 1-77, 1-81, 1-82, 1-83, 1-84, 1-87, 1-88, 1-89, 1-91, 1-92, 1-95, 1-97, 1-100, 1-101, 1-103, 1-115, 1-122, 1-124, 1-126, 1-129, 1-130, 1-132, 1-134, 1-135, 1-136, 1-137 and 1-147 showed excellent activity of Grade A at 50 ppm.

[0205] Test Example 3. Insecticidal test against western flower thrips (Frankliniella occidentalis) Female western flower thrips (F. occidentalis) were inoculated onto kidney bean leaf pieces, and after one day of egg laying, the female adults were removed. After a further three days, the number of hatched larvae on the leaf pieces was counted, and then a solution of a pesticide containing a compound listed in Tables 1 to 5 as an active ingredient, diluted to 50 ppm or 500 ppm, was sprayed onto the leaves. Four days after treatment, the number of surviving larvae of this species was counted, and the corrected mortality rate was calculated using the following formula and evaluated according to the criteria of Test Example 1. A duplicate run was conducted.

[0206]

number

[0207] As a result, among the compounds represented by the general formula (1) of the present invention against the citrus leafminer, the compounds with compound numbers 1-6, 1-7, 1-16, 1-18, 1-19, 1-22, 1-39, 1-40, 1-46, 1-47, 1-48, 1-50, 1-53, 1-56, 1-57, 1-58, 1-59, 1-60, 1-61, 1-62, 1-63, 1-64, 1-67, 1-69, 1-72, 1-75, 1-76, 1-77, 1-81, 1-82, 1-83, 1-84, 1-88, 1-89, 1-91, 1-92, 1-95, 1-97, 1-100, 1-101, 1-103, 1-112, 1-113, 1-115, 1-121, 1-122, 1-124, 1-128, 1-129, 1-130, 1-132, 1-134, 1-135, 1-136, 1-138, 1-139, 1-145, 1-147 and 2-1 showed an activity of Grade A at 500 ppm. In particular, the compounds with compound numbers 1-16, 1-18, 1-19, 1-22, 1-40, 1-46, 1-50, 1-56, 1-59, 1-60, 1-61, 1-62, 1-63, 1-64, 1-67, 1-69, 1-72, 1-76, 1-77, 1-82, 1-83, 1-84, 1-88, 1-89, 1-91, 1-92, 1-97, 1-100, 1-101, 1-112, 1-113, 1-115, 1-122, 1-128, 1-129, 1-130, 1-132, 1-134, 1-136, 1-147 and 2-1 showed excellent activity of Grade A at 50 ppm.

Industrial Applicability

[0208] The compound of the present invention or a salt thereof has an excellent effect as an agricultural and horticultural insecticide.

Claims

1. General formula (1) 【Chemical 1】 {In the formula,[[]] R １ is (a1) an aryl group; (a2) a substituted aryl group having one or more substituents independently selected from the substituent group A on the ring; (a3) a 5- to 10-membered heterocyclic group; or (a4) a substituted 5- to 10-membered heterocyclic group having one or more substituents independently selected from the substituent group A on the ring. R ２ is (b1) (C １ -C ６ ) alkyl group; (b2) (C ２ -C ６ ) alkenyl group; (b3) (C ２ -C ６ ) an alkynyl group; (b4) (C ３ -C ６ ) cycloalkyl group; (b5) halo (C １ -C ６ ) alkyl group; (b6) halo (C ２ -C ６ ) alkenyl group; (b7) halo (C ２ -C ６ (b8) a substituted (C) alkynyl group having 1 to 3 substituents independently selected from the substituent group B; １ -C ６ (b9) a substituted (C) alkyl group having 1 to 3 substituents independently selected from the substituent group C on the ring; ３ -C ６ ) cycloalkyl group; (b10) N,N-di(C １ -C ６ ) alkylamino group; (b11) N—(C １ -C ６ ) alkyl-N-phenylamino group; (b12) (C １ -C ６ ) alkylsulfonyl group; (b13) N—(C １ -C ６ )(b14) a piperidinyl group; (b15) a morpholinyl group; (b16) a phenyl group; (b17) a substituted phenyl group having 1 to 5 substituents independently selected from the substituent group D on the ring; (b18) a pyridyl group; (b19) a substituted pyridyl group having 1 to 4 substituents independently selected from the substituent group D on the ring; (b20) a pyridazinyl group; (b21) a substituted pyridazinyl group having 1 to 3 substituents independently selected from the substituent group D on the ring; (b22) a pyrimidinyl group; (b23) a substituted pyrimidinyl group having 1 to 3 substituents independently selected from the substituent group D on the ring; (b24) a pyrazinyl group; (b25) a substituted pyrazinyl group having 1 to 3 substituents independently selected from the substituent group D on the ring; (b26) a triazinyl group; (b27) a substituted triazinyl group having 1 to 2 substituents independently selected from the substituent group D on the ring; (b28) a furanyl group; (b29) a substituted furanyl group having 1 to 3 substituents independently selected from the substituent group D on the ring; (b30) an oxazolyl group; (b31) a substituted oxazolyl group having 1 to 2 substituents independently selected from the substituent group D on the ring; (b32) an isoxazolyl group; (b33) a substituted isoxazolyl group having 1 to 2 substituents independently selected from the substituent group D on the ring; (b34) a thienyl group; (b35) a substituted thienyl group having 1 to 3 substituents independently selected from the substituent group D on the ring; (b36) a thiazolyl group; (b37) a substituted thiazolyl group having 1 to 2 substituents independently selected from the substituent group D on the ring; (b38) an isothiazolyl group; (b39) a substituted isothiazolyl group having 1 to 2 substituents independently selected from the substituent group D on the ring; (b40) a thiadiazolyl group; (b41) a substituted thiadiazolyl group having 1 substituent selected from the substituent group D on the ring; (b42) a pyrazolyl group; (b43) a substituted pyrazolyl group having 1 to 3 substituents independently selected from the substituent group D on the ring; (b44) a triazolyl group; (b45) a substituted triazolyl group having 1 to 2 substituents independently selected from the substituent group D on the ring;(b46) tetrazolyl group; (b47) a substituted tetrazolyl group having one substituent selected from the substituent group D on the ring; (b48) benzoxazolyl group; (b49) a substituted benzoxazolyl group having 1 to 4 substituents independently selected from the substituent group D on the ring; (b50) benzothiazolyl group; (b51) a substituted benzothiazolyl group having 1 to 4 substituents independently selected from the substituent group D on the ring; (b52) quinolinyl group; (b53) a substituted quinolinyl group having 1 to 6 substituents independently selected from the substituent group D on the ring; (b54) naphthyl group; (b55) a substituted naphthyl group having 1 to 7 substituents independently selected from the substituent group D on the ring; (b56) tetrahydronaphthyl group; (b57) a substituted tetrahydronaphthyl group having 1 to 10 substituents independently selected from the substituent group D on the ring; (b58) phenyl(C; １ -C ６ )alkyl group; (b59) a substituted phenyl(C １ -C ６ )alkyl group having 1 to 5 substituents independently selected from the substituent group D on the ring; (b60) pyridyl(C １ -C ６ )alkyl group; (b61) a substituted pyridyl(C １ -C ６ )alkyl group having 1 to 4 substituents independently selected from the substituent group D on the ring; (b62) pyrazinyl(C １ -C ６ )alkyl group; (b63) a substituted pyrazinyl(C １ -C ６ )alkyl group having 1 to 3 substituents independently selected from the substituent group D on the ring; (b64) pyrimidinyl(C １ -C ６ )alkyl group; (b65) a substituted pyrimidinyl(C １ -C ６ )alkyl group having 1 to 3 substituents independently selected from the substituent group D on the ring; (b66) furanyl(C １ -C ６ )(b67) a substituted furanyl having on the ring from 1 to 3 substituents each independently selected from the substituent group D; an alkyl group (C １ -C ６ )(b68) a thienyl (C １ -C ６ )(b69) a substituted thienyl having on the ring from 1 to 3 substituents each independently selected from the substituent group D; an alkyl group (C １ -C ６ )(b70) an amino group; or (b71) an N,N-di(C １ -C ６ )alkylaminosulfonyl group. R ３ is (c1) a hydrogen atom; (c2) a (C １ -C ６ ) alkyl group; (c3) a (C ３ -C ６ ) cycloalkyl group; (c4) a (C １ -C ６ ) alkoxy group; or (c5) a (C １ -C ６ ) alkylcarbonyl group. R ２ and R ３ are bonded to each other and may be substituted with 1 to 6 substituents selected from the group consisting of a halogen atom, a (C １ -C ６ ) alkyl group, and a halo(C １ -C ６ ) alkyl group, and may form a 3- to 7-membered nitrogen-containing heterocyclic ring or a ring formed by condensation of the nitrogen-containing heterocyclic ring and a benzene ring. Y represents an oxygen atom or a sulfur atom. Z is an oxygen atom, a sulfur atom, or a NOR ４ group (wherein, R ４ is a hydrogen atom, (C １ -C ６ ) alkyl group, or halo(C １ -C ６ ) alkyl group.). The substituent group A is, (d1) halogen atom; (d2) cyano group; (d3) nitro group; (d4) hydroxyl group; (d5) carboxyl group; (d6) (C １ -C ６ ) alkyl group; (d7) (C ２ -C ６ ) alkenyl group; (d8) (C ２ -C ６ ) alkynyl group; (d9) (C １ -C ６ ) alkoxy group; (d10) (C ３ -C ６ ) cycloalkyl group; (d11) (C １ -C ６ ) alkylthio group; (d12) (C １ -C ６ ) alkylsulfinyl group; (d13) (C １ -C ６ ) alkylsulfonyl group; (d14) halo(C １ -C ６ ) alkyl group; (d15) halo(C ２ -C ６ ) alkenyl group; (d16) halo(C ２ -C ６ ) alkynyl group; (d17) halo(C １ -C ６ ) alkoxy group; (d18) halo(C ３ -C ６ ) cycloalkyl group; (d19) halo(C １ -C ６ ) alkylthio group; (d20) halo(C １ -C ６ ) alkylsulfinyl group; (d21) halo(C １ -C ６ ) alkylsulfonyl group; (d22) N,N-di(C １ -C ６ ) alkylaminosulfonyl group; (d23) halogen atom, cyano group, (C １ -C ６ ) alkyl group, (C １ -C ６ ) alkoxy group and (C １ -C ６ having on the ring 1 to 3 substituents each independently selected from the group consisting of alkylcarbonyl groups, substituted (C ３ - C ６ ) cycloalkyl group; (d24) R ５ - (R ６ - N=)O=S group (wherein R ５ is a (C １ - C ６ ) alkyl group, a (C ３ - C ６ ) cycloalkyl group, a halo(C １ - C ６ ) alkyl group, or a (C １ - C ６ ) alkoxy(C １ - C ６ ) alkyl group, and R ６ is a hydrogen atom, a cyano group, a (C １ - C ６ ) alkyl group, a (C ３ - C ６ ) cycloalkyl group, a halo(C １ - C ６ ) alkyl group, a (C １ - C ６ ) alkylcarbonyl group, or a halo(C １ - C ６ ) alkylcarbonyl group.); (d25) SF ５ group; (d26) a (C １ - C ６ ) alkoxy(C １ - C ６ ) alkyl group; (d27) a (C １ - C ６ ) alkoxy(C １ - C ６ ) alkoxy group; (d28) a (C １ - C ６ ) alkylcarbonylamino group; (d29) a halo(C １ - C ６ ) alkylcarbonylamino group; (d30) a (C １ - C ６ ) alkylsulfonylamino group; (d31) a halo(C １ - C ６ ) alkylsulfonylamino group; (d32) a (C １ - C ６ ), an alkoxycarbonyl group; (d33) a methylenedioxy group optionally substituted with one or two substituents selected from the group consisting of a halogen atom, a phenyl group, and a (C １ -C ６ ), an alkyl group; (d34) an N-(C １ -C ６ ), an alkylaminocarbonyl group; (d35) an N-halo(C １ -C ６ ), an alkylaminocarbonyl group; (d36) a furanyl group; (d37) a halogen atom, a cyano group, a (C １ -C ６ ), an alkyl group, a (C １ -C ６ ), an alkoxy group, a halo(C １ -C ６ ), an alkyl group, and a halo(C １ -C ６ ), an alkoxy group, and a substituted furanyl group having one to three substituents each independently selected from the group consisting of a halogen atom, a cyano group, a (C １ -C ６ ), an alkyl group, a (C １ -C ６ ), an alkoxy group, a halo(C １ -C ６ ), an alkyl group, and a halo(C １ -C ６ ), an alkoxy group, and a substituted oxazolyl group having one to two substituents each independently selected from the group consisting of a halogen atom, a cyano group, a (C １ -C ６ ), an alkyl group, a (C １ -C ６ ), an alkoxy group, a halo(C １ -C ６ ), an alkyl group, and a halo(C １ -C ６ ), an alkoxy group, and a substituted isoxazolyl group having one to two substituents each independently selected from the group consisting of a halogen atom, a cyano group, a (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, (C ３ -C ６ ), a cycloalkyl group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), an alkoxy group, having on the ring one substituent selected from the group consisting of; (d44) a thienyl group; (d45) a halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, (C ３ -C ６ ), a cycloalkyl group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), an alkoxy group, having on the ring one to three substituents each independently selected from the group consisting of; (d46) a thiazolyl group; (d47) a halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), an alkoxy group, having on the ring one to two substituents each independently selected from the group consisting of; (d48) an isothiazolyl group; (d49) a halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), an alkoxy group, having on the ring one to two substituents each independently selected from the group consisting of; (d50) a thiadiazolyl group; (d51) a halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), an alkoxy group, and a substituted thiadiazolyl group having on the ring one substituent selected from the group consisting thereof; (d52) a pyrrolyl group; (d53) a halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), an alkoxy group, and a substituted pyrrolyl group having on the ring one to three substituents each independently selected from the group consisting thereof; (d54) a pyrazolyl group; (d55) a halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), an alkoxy group, and a substituted pyrazolyl group having on the ring one or two substituents each independently selected from the group consisting thereof; (d56) an imidazolyl group; (d57) a halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), an alkoxy group, and a substituted imidazolyl group having on the ring one or two substituents each independently selected from the group consisting thereof; (d58) a triazolyl group; (d59) a halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), a substituted triazolyl group having on the ring one substituent selected from the group consisting of an alkyl group and halo(C １ -C ６ ), a tetrazolyl group; (d60) a halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), a substituted tetrazolyl group having on the ring one substituent selected from the group consisting of an alkoxy group; (d62) an oxazolinyl group; (d63) a halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), a substituted oxazolinyl group having on the ring from 1 to 4 substituents each independently selected from the group consisting of an alkoxy group; (d64) a thiazolinyl group; (d65) a halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), a substituted thiazolinyl group having on the ring from 1 to 4 substituents each independently selected from the group consisting of an alkoxy group; (d66) an isoxazolinyl group; (d67) a halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ A substituted isoxazolinyl group having 1 to 4 substituents independently selected from the group consisting of alkoxy groups on the ring; (d68) an isothiazolinyl group; (d69) a halogen atom, a cyano group, (C １ -C ６ An alkyl group, (C １ -C ６ An alkoxy group, halo(C １ -C ６ An alkyl group and halo(C １ -C ６ A substituted isothiazolinyl group having 1 to 4 substituents independently selected from the group consisting of alkoxy groups on the ring; (d70) a pyrrolidinyl group; (d71) a halogen atom, a cyano group, (C １ -C ６ An alkyl group, (C １ -C ６ An alkoxy group, halo(C １ -C ６ An alkyl group and halo(C １ -C ６ A substituted pyrrolidinyl group having 1 to 4 substituents independently selected from the group consisting of alkoxy groups on the ring; (d72) an imidazolinyl group; (d73) a halogen atom, a cyano group, (C １ -C ６ An alkyl group, (C １ -C ６ An alkoxy group, halo(C １ -C ６ An alkyl group and halo(C １ -C ６ A substituted imidazolinyl group having 1 to 4 substituents independently selected from the group consisting of alkoxy groups on the ring; (d74) a phenyl group; (d75) a halogen atom, a cyano group, (C １ -C ６ An alkyl group, (C １ -C ６ An alkoxy group, (C ３ -C ６ A cycloalkyl group, halo(C １ -C ６ An alkyl group and halo(C １ -C ６ A substituted phenyl group having 1 to 5 substituents independently selected from the group consisting of alkoxy groups on the ring; (d76) a pyridyl group; (d77) a halogen atom, a cyano group, (C １ -C ６ ) an alkyl group, (C １ -C ６ ) an alkoxy group, halo(C １ -C ６ ), an alkyl group, and halo(C １ -C ６ ), a substituted pyridyl group having 1 to 4 substituents independently selected from the group consisting of an alkoxy group, on the ring; (d78) a pyridazinyl group; (d79) a halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group, and halo(C １ -C ６ ), a substituted pyridazinyl group having 1 to 3 substituents independently selected from the group consisting of an alkoxy group, on the ring; (d80) a pyrimidinyl group; (d81) a halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group, and halo(C １ -C ６ ), a substituted pyrimidinyl group having 1 to 3 substituents independently selected from the group consisting of an alkoxy group, on the ring; (d82) a pyrazinyl group; (d83) a halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group, and halo(C １ -C ６ ), a substituted pyrazinyl group having 1 to 3 substituents independently selected from the group consisting of an alkoxy group, on the ring; (d84) a triazinyl group; (d85) a halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C[[ID=6l]] ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group, and halo(C １ -C ６ A substituted triazinyl group having 1 to 2 substituents independently selected from the group consisting of alkoxy groups on the ring; (d86) Dihydrofuranyl group; (d87) Dihydropyranyl group; (d88) Phenyloxy group; (d89) Halogen atom, cyano group, (C １ -C ６ An alkyl group, (C １ -C ６ An alkoxy group, halo(C １ -C ６ An alkyl group and halo(C １ -C ６ A substituted phenyloxy group having 1 to 5 substituents independently selected from the group consisting of an alkoxy group on the ring; (d90) Phenyl(C １ -C ６ An alkoxy group; (d91) Halogen atom, cyano group, (C １ -C ６ An alkyl group, (C １ -C ６ An alkoxy group, halo(C １ -C ６ An alkyl group and halo(C １ -C ６ A substituted phenyl(C １ -C ６ An alkoxy group; (d92) Phenyl(C １ -C ６ An alkylthio group; (d93) Halogen atom, cyano group, (C １ -C ６ An alkyl group, (C １ -C ６ An alkoxy group, halo(C １ -C ６ An alkyl group and halo(C １ -C ６ A substituted phenyl(C １ -C ６ An alkylthio group; (d94) Tri(C １ -C ６ An alkylsilyl(C ２ -C ６ ) alkynyl group; (d95) aminosulfonyl group; and (d96) N-(C １ -C ６ ) consisting of an alkylaminosulfonyl group. The substituent group B is, (e1) cyano group; (e2) (C ３ -C ６ )cycloalkyl group; (e3) (C １ -C ６ )alkoxy group; (e4) (C １ -C ６ )alkylthio group; (e5) (C １ -C ６ )alkylsulfinyl group; (e6) (C １ -C ６ )alkylsulfonyl group; (e7) halo(C ３ -C ６ )cycloalkyl group; (e8) halo(C １ -C ６ )alkoxy group; (e9) halo(C １ -C ６ )alkylthio group; (e10) halo(C １ -C ６ )alkylsulfinyl group; (e11) halo(C １ -C ６ )alkylsulfonyl group; (e12) (C １ -C ６ )alkoxycarbonyl group; (e13) aminocarbonyl group; and (e14) phenylcarbonyl group. The substituent group C is, (f1) cyano group; (f2) (C １ -C ６ ) alkyl group; (f3) (C ２ -C ６ ) alkenyl group; (f4) (C ２ -C ６ ) alkynyl group; (f5) (C ３ -C ６ ) cycloalkyl group; (f6) (C １ -C ６ ) alkoxy group; (f7) (C １ -C ６ ) alkylthio group; (f8) (C １ -C ６ ) alkylsulfinyl group; (f9) (C １ -C ６ ) alkylsulfonyl group; (f10) halo(C １ -C ６ ) alkyl group; (f11) halo(C ３ -C ６ ) cycloalkyl group; (f12) halo(C １ -C ６ ) alkoxy group; (f13) halo(C １ -C ６ ) alkylthio group; (f14) halo(C １ -C ６ ) alkylsulfinyl group; (f15) halo(C １ -C ６ ) alkylsulfonyl group; (f16) aminocarbonyl group; and (f17) phenyl group. The substituent group D is, (g1) halogen atom; (g2) cyano group; (g3) nitro group; (g4) amino group; (g5) hydroxyl group; (g6) carboxyl group; (g7) (C １ -C ６ ) alkyl group; (g8) (C １ -C ６ ) alkoxy group; (g9) (C ３ -C ６ ) cycloalkyl group; (g10) (C １ -C ６ ) alkylthio group; (g11) (C １ -C ６ ) alkylsulfinyl group; (g12) (C １ -C ６ ) alkylsulfonyl group; (g13) halo(C １ -C ６ ) alkyl group; (g14) halo(C １ -C ６ ) alkoxy group; (g15) halo(C ３ -C ６ ) cycloalkyl group; (g16) halo(C １ -C ６ ) alkylthio group; (g17) halo(C １ -C ６ ) alkylsulfinyl group; (g18) halo(C １ -C ６ ) alkylsulfonyl group; (g19) (C １ -C ６ ) alkoxycarbonyl group; (g20) phenyl(C １ -C ６ ) alkoxycarbonyl group; (g21) (C １ -C ６ ) alkylaminocarbonyl group; (g22) N-halo(C １ -C ６ ) alkylaminocarbonyl group; (g23) phenyl group; (g24) halogen atom, cyano group, (C １ -C ６ ) alkyl group, (C １ -C ６ ) alkoxy group, halo(C １ -C ６ ) alkyl group and halo(C １ -C ６ A substituted phenyl group having 1 to 5 substituents independently selected from the group consisting of alkoxy groups on the ring; and (g25) a halogen atom, a phenyl group, and (C formed by two adjacent substituents together １ -C ６ It consists of a methylenedioxy group which may be substituted with 1 to 2 substituents selected from the group consisting of an alkyl group). However, R １ is a (C 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 )alkylaminosulfonyl group, and R ５ -(R ６ -N=)O=S group (wherein R ５ is a (C １ -C ６ )alkyl group, (C ３ -C ６ )cycloalkyl group, halo(C １ -C ６ )alkyl group, or (C １ -C ６ )alkoxy(C １ -C ６ )alkyl group, and R ６ is a hydrogen atom, cyano group, (C １ -C ６ )alkyl group, (C ３ -C ６ )cycloalkyl group, halo(C １ -C ６ )alkyl group, (C １ -C ６ )alkylcarbonyl group, or halo(C １ -C ６ )alkylcarbonyl group. ) is unsubstituted. } a compound represented by or a salt thereof.

2. R ２ 、R ３ 、Y, Z, the substituent groups A, B, C and D are the same as in claim 1, R １ is (a5) phenyl group; (a6) a substituted phenyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a7) pyridyl group; (a8) a substituted pyridyl group having 1 to 4 substituents independently selected from the group of substituents A on the ring; (a9) pyridazinyl group; (a10) a substituted pyridazinyl group having 1 to 3 substituents independently selected from the group of substituents A on the ring; (a11) pyrimidinyl group; (a12) a substituted pyrimidinyl group having 1 to 3 substituents independently selected from the group of substituents A on the ring; (a13) pyrazinyl group; (a14) a substituted pyrazinyl group having 1 to 3 substituents independently selected from the group of substituents A on the ring; (a15) triazinyl group; (a16) a substituted triazinyl group having 1 to 2 substituents independently selected from the group of substituents A on the ring; (a17) 2-oxopyridyl group; (a18) a substituted 2-oxopyridyl group having 1 to 4 substituents independently selected from the group of substituents A on the ring; (a19) furanyl group; (a20) a substituted furanyl group having 1 to 3 substituents independently selected from the group of substituents A on the ring; (a21) oxazolyl group; (a22) a substituted oxazolyl group having 1 to 2 substituents independently selected from the group of substituents A on the ring; (a23) isoxazolyl group; (a24) a substituted isoxazolyl group having 1 to 2 substituents independently selected from the group of substituents A on the ring; (a25) oxadiazinyl group; (a26) a substituted oxadiazinyl group having 1 substituent selected from the group of substituents A on the ring; (a27) thienyl group; (a28) a substituted thienyl group having 1 to 3 substituents independently selected from the group of substituents A on the ring; (a29) thiazolyl group; (a30) a substituted thiazolyl group having 1 to 2 substituents independently selected from the group of substituents A on the ring; (a31) isothiazolyl group; (a32) a substituted isothiazolyl group having 1 to 2 substituents independently selected from the group of substituents A on the ring; (a33) thiadiazolyl group; (a34) a substituted thiadiazolyl group having 1 substituent selected from the group of substituents A on the ring; (a35) pyrrolyl group;(a36) A substituted pyrrolyl group having 1 to 4 substituents independently selected from the group of substituents A on the ring; (a37) A pyrazolyl group; (a38) A substituted pyrazolyl group having 1 to 3 substituents independently selected from the group of substituents A on the ring; (a39) An imidazolyl group; (a40) A substituted imidazolyl group having 1 to 3 substituents independently selected from the group of substituents A on the ring; (a41) A triazolyl group; (a42) A substituted triazolyl group having 1 to 2 substituents independently selected from the group of substituents A on the ring; (a43) A tetrazolyl group; (a44) A substituted tetrazolyl group having 1 substituent selected from the group of substituents A on the ring; (a45) A benzofuranyl group; (a46) A substituted benzofuranyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a47) A benzoxazolyl group; (a48) A substituted benzoxazolyl group having 1 to 4 substituents independently selected from the group of substituents A on the ring; (a49) A benzisoxazolyl group; (a50) A substituted benzisoxazolyl group having 1 to 4 substituents independently selected from the group of substituents A on the ring; (a51) A benzothienyl group; (a52) A substituted benzothienyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a53) A benzothiazolyl group; (a54) A substituted benzothiazolyl group having 1 to 4 substituents independently selected from the group of substituents A on the ring; (a55) A benzisothiazolyl group; (a56) A substituted benzisothiazolyl group having 1 to 4 substituents independently selected from the group of substituents A on the ring; (a57) An indolyl group; (a58) A substituted indolyl group having 1 to 6 substituents independently selected from the group of substituents A on the ring; (a59) An isoindolyl group; (a60) A substituted isoindolyl group having 1 to 6 substituents independently selected from the group of substituents A on the ring; (a61) An indazolyl group; (a62) A substituted indazolyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a63) A benzimidazolyl group; (a64) A substituted benzimidazolyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring;(a65) a benzotriazolyl group; (a66) a substituted benzotriazolyl group having 1 to 4 substituents each independently selected from the substituent group A on the ring; (a67) a furopyridyl group; (a68) a substituted furopyridyl group having 1 to 4 substituents each independently selected from the substituent group A on the ring; (a69) a thienopyridyl group; (a70) a substituted thienopyridyl group having 1 to 4 substituents each independently selected from the substituent group A on the ring; (a71) a thiazolopyridyl group; (a72) a substituted thiazolopyridyl group having 1 to 4 substituents each independently selected from the substituent group A on the ring; (a73) an imidazopyridyl group; (a74) a substituted imidazopyridyl group having 1 to 5 substituents each independently selected from the substituent group A on the ring; (a75) an indolizinyl group; (a76) a substituted indolizinyl group having 1 to 6 substituents each independently selected from the substituent group A on the ring; (a77) a pyrrolopyridyl group; (a78) a substituted pyrrolopyridyl group having 1 to 5 substituents each independently selected from the substituent group A on the ring; (a79) a pyrrolopyrimidinyl group; (a80) a substituted pyrrolopyrimidinyl group having 1 to 5 substituents each independently selected from the substituent group A on the ring; (a81) an oxazolopyridyl group; (a82) a substituted oxazolopyridyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (a83) an isoxazolopyridyl group; (a84) a substituted isoxazolopyridyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (a85) an isothiazolopyridyl group; (a86) a substituted isothiazolopyridyl group having 1 to 3 substituents each independently selected from the substituent group A on the ring; (a87) an imidazopyrimidinyl group; (a88) a substituted imidazopyrimidinyl group having 1 to 5 substituents each independently selected from the substituent group A on the ring; (a89) a pyrazolopyridyl group; (a90) a substituted pyrazolopyridyl group having 1 to 5 substituents each independently selected from the substituent group A on the ring; (a91) a pyrazolopyrimidinyl group; (a92) a substituted pyrazolopyrimidinyl group having 1 to 5 substituents each independently selected from the substituent group A on the ring; (a93) a triazolopyridyl group;(a94) A substituted triazolopyridyl group having 1 to 4 substituents independently selected from the group of substituents A on the ring; (a95) A triazolopyrimidinyl group; (a96) A substituted triazolopyrimidinyl group having 1 to 4 substituents independently selected from the group of substituents A on the ring; (a97) A quinoxalinyl group; (a98) A substituted quinoxalinyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a99) A quinolinyl group; (a100) A substituted quinolinyl group having 1 to 6 substituents independently selected from the group of substituents A on the ring; (a101) A naphthyl group; (a102) A substituted naphthyl group having 1 to 7 substituents independently selected from the group of substituents A on the ring; (a103) An isoquinolinyl group; (a104) A substituted isoquinolinyl group having 1 to 6 substituents independently selected from the group of substituents A on the ring; (a105) A cinnolinyl group; (a106) A substituted cinnolinyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a107) A phthalazinyl group; (a108) A substituted phthalazinyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a109) A quinazolinyl group; (a110) A substituted quinazolinyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a111) A naphthyridinyl group; or (a112) A substituted naphthyridinyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring, the compound according to claim 1 or a salt thereof.;

3. R １ is (a5) phenyl group; (a6) a substituted phenyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a7) pyridyl group; (a8) a substituted pyridyl group having 1 to 4 substituents independently selected from the group of substituents A on the ring; (a9) pyridazinyl group; (a10) a substituted pyridazinyl group having 1 to 3 substituents independently selected from the group of substituents A on the ring; (a11) pyrimidinyl group; (a12) a substituted pyrimidinyl group having 1 to 3 substituents independently selected from the group of substituents A on the ring; (a13) pyrazinyl group; (a14) a substituted pyrazinyl group having 1 to 3 substituents independently selected from the group of substituents A on the ring; (a15) triazinyl group; (a16) a substituted triazinyl group having 1 to 2 substituents independently selected from the group of substituents A on the ring; (a17) 2-oxopyridyl group; (a18) a substituted 2-oxopyridyl group having 1 to 4 substituents independently selected from the group of substituents A on the ring; (a27) thienyl group; (a28) a substituted thienyl group having 1 to 3 substituents independently selected from the group of substituents A on the ring; (a97) quinoxalinyl group; (a98) a substituted quinoxalinyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a99) quinolinyl group; (a100) a substituted quinolinyl group having 1 to 6 substituents independently selected from the group of substituents A on the ring; (a101) naphthyl group; (a102) a substituted naphthyl group having 1 to 7 substituents independently selected from the group of substituents A on the ring; (a103) isoquinolinyl group; (a104) a substituted isoquinolinyl group having 1 to 6 substituents independently selected from the group of substituents A on the ring; (a105) cinnolinyl group; (a106) a substituted cinnolinyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a107) phthalazinyl group; (a108) a substituted phthalazinyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a109) quinazolinyl group; (a110) a substituted quinazolinyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a111) naphthyridinyl group;or a substituted naphthyridinyl group having from 1 to 5 substituents independently selected from the group A on the ring; R ２ is (b1) (C １ -C ６ ) alkyl group; (b2) (C ２ -C ６ ) alkenyl group; (b3) (C ２ -C ６ ) alkynyl group; (b4) (C ３ -C ６ ) cycloalkyl group; (b5) halo(C １ -C ６ ) alkyl group; (b6) halo(C ２ -C ６ ) alkenyl group; (b7) halo(C ２ -C ６ ) alkynyl group; (b8) substituted (C １ -C ６ ) alkyl group having 1 to 3 substituents independently selected from substituent group B; (b9) substituted (C ３ -C ６ )(b14) a piperidinyl group; (b15) a morpholinyl group; (b16) a phenyl group; (b17) a substituted phenyl group having from 1 to 5 substituents independently selected from the group of substituents D on the ring; (b18) a pyridyl group; (b19) a substituted pyridyl group having from 1 to 4 substituents independently selected from the group of substituents D on the ring; (b20) a pyridazinyl group; (b21) a substituted pyridazinyl group having from 1 to 3 substituents independently selected from the group of substituents D on the ring; (b22) a pyrimidinyl group; (b23) a substituted pyrimidinyl group having from 1 to 3 substituents independently selected from the group of substituents D on the ring; (b24) a pyrazinyl group; (b25) a substituted pyrazinyl group having from 1 to 3 substituents independently selected from the group of substituents D on the ring; (b26) a triazinyl group; (b27) a substituted triazinyl group having from 1 to 2 substituents independently selected from the group of substituents D on the ring; (b28) a furanyl group; (b29) a substituted furanyl group having from 1 to 3 substituents independently selected from the group of substituents D on the ring; (b30) an oxazolyl group; (b31) a substituted oxazolyl group having from 1 to 2 substituents independently selected from the group of substituents D on the ring; (b32) an isoxazolyl group; (b33) a substituted isoxazolyl group having from 1 to 2 substituents independently selected from the group of substituents D on the ring; (b34) a thienyl group; (b35) a substituted thienyl group having from 1 to 3 substituents independently selected from the group of substituents D on the ring; (b36) a thiazolyl group; (b37) a substituted thiazolyl group having from 1 to 2 substituents independently selected from the group of substituents D on the ring; (b38) an isothiazolyl group; (b39) a substituted isothiazolyl group having from 1 to 2 substituents independently selected from the group of substituents D on the ring; (b40) a thiadiazolyl group; (b41) a substituted thiadiazolyl group having 1 substituent selected from the group of substituents D on the ring; (b42) a pyrazolyl group; (b43) a substituted pyrazolyl group having from 1 to 3 substituents independently selected from the group of substituents D on the ring; (b44) a triazolyl group; (b45) a substituted triazolyl group having from 1 to 2 substituents independently selected from the group of substituents D on the ring; (b46) a tetrazolyl group;(b47) A substituted tetrazolyl group having one substituent selected from the group of substituents D on the ring; (b54) A naphthyl group; (b55) A substituted naphthyl group having 1 to 7 substituents each independently selected from the group of substituents D on the ring; (b58) Phenyl(C; １ -C ６ )alkyl group; (b59) Substituted phenyl(C １ -C ６ )alkyl group having 1 to 5 substituents each independently selected from the group of substituents D on the ring; (b60) Pyridyl(C １ -C ６ )alkyl group; (b61) Substituted pyridyl(C １ -C ６ )alkyl group having 1 to 4 substituents each independently selected from the group of substituents D on the ring; (b62) Pyrazinyl(C １ -C ６ )alkyl group; (b63) Substituted pyrazinyl(C １ -C ６ )alkyl group having 1 to 3 substituents each independently selected from the group of substituents D on the ring; (b64) Pyrimidinyl(C １ -C ６ )alkyl group; (b65) Substituted pyrimidinyl(C １ -C ６ )alkyl group having 1 to 3 substituents each independently selected from the group of substituents D on the ring; (b66) Furanyl(C １ -C ６ )alkyl group; (b67) Substituted furanyl(C １ -C ６ )alkyl group having 1 to 3 substituents each independently selected from the group of substituents D on the ring; (b68) Thienyl(C １ -C ６ )alkyl group; (b69) Substituted thienyl(C １ -C ６ )alkyl group having 1 to 3 substituents each independently selected from the group of substituents D on the ring; or (b70) An amino group, R ３ is (c1) a hydrogen atom; (c2) a (C １ -C ６ ) alkyl group; or (c3) a (C ３ -C ６ ) cycloalkyl group, and R ２ and R ３ are bonded to each other and may be substituted with 1 to 6 substituents selected from the group consisting of a halogen atom, a (C １ -C ６ )alkyl group, and a halo(C １ -C ６ )alkyl group, and may form a 3- to 7-membered nitrogen-containing heterocyclic ring or a ring in which the nitrogen-containing heterocyclic ring and a benzene ring are condensed, Y is an oxygen atom or a sulfur atom, Z is an oxygen atom, a sulfur atom, or a NOR ４ group (wherein R ４ is a hydrogen atom, (C １ -C ６ ) alkyl group, or halo(C １ -C ６ ) alkyl group.). The substituent group A is, (d1) A halogen atom; (d2) A cyano group; (d6) (C １ -C ６ )(alkyl group); (d7) (C ２ -C ６ )(alkenyl group); (d8) (C ２ -C ６ )(alkynyl group); (d9) (C １ -C ６ )(alkoxy group); (d10) (C ３ -C ６ )(cycloalkyl group); (d11) (C １ -C ６ )(alkylthio group); (d12) (C １ -C ６ )(alkylsulfinyl group); (d13) (C １ -C ６ )(alkylsulfonyl group); (d14) Halo(C １ -C ６ )(alkyl group); (d15) Halo(C ２ -C ６ )(alkenyl group); (d16) Halo(C ２ -C ６ )(alkynyl group); (d17) Halo(C １ -C ６ )(alkoxy group); (d18) Halo(C ３ -C ６ )(cycloalkyl group); (d19) Halo(C １ -C ６ )(alkylthio group); (d20) Halo(C １ -C ６ )(alkylsulfinyl group); (d21) Halo(C １ -C ６ )(alkylsulfonyl group); (d22) N,N-di(C １ -C ６ )(alkylaminosulfonyl group); (d23) A halogen atom, a cyano group, (C １ -C ６ )(alkyl group), (C １ -C ６ )(alkoxy group) and (C １ -C ６ )(alkylcarbonyl group), each independently selected from the group consisting of 1 to 3 substituents, having on the ring a substituted (C ３ -C ６ ) cycloalkyl group; (d26) (C １ -C ６ ) alkoxy (C １ -C ６ ) alkyl group; (d27) (C １ -C ６ ) alkoxy (C １ -C ６ ) alkoxy group; (d32) (C １ -C ６ ) alkoxycarbonyl group; (d33) A methylenedioxy group optionally substituted with 1 to 2 substituents selected from the group consisting of a halogen atom, a phenyl group, and (C １ -C ６ ) alkyl group, formed by two adjacent substituents together; (d36) furanyl group; (d37) halogen atom, cyano group, (C １ -C ６ ) alkyl group, (C １ -C ６ ) alkoxy group, halo(C １ -C ６ ) alkyl group, and halo(C １ -C ６ ) alkoxy group; a substituted furanyl group having 1 to 3 substituents independently selected from the group on the ring; (d38) oxazolyl group; (d39) halogen atom, cyano group, (C １ -C ６ ) alkyl group, (C １ -C ６ ) alkoxy group, halo(C １ -C ６ ) alkyl group, and halo(C １ -C ６ ) alkoxy group; a substituted oxazolyl group having 1 to 2 substituents independently selected from the group on the ring; (d40) isoxazolyl group; (d41) halogen atom, cyano group, (C １ -C ６ ) alkyl group, (C １ -C ６ ) alkoxy group, halo(C １ -C ６ ) alkyl group, and halo(C １ -C ６ A substituted isoxazolyl group having 1 to 2 substituents independently selected from the group consisting of alkoxy groups on the ring; (d42) an oxadiazolyl group; (d43) a halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, (C ３ -C ６ ), a cycloalkyl group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), an alkoxy group, a substituted oxadiazolyl group having 1 substituent selected from the group consisting of halo(C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), an alkoxy group on the ring; (d52) a pyrrolyl group; (d53) a halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), an alkoxy group, a substituted pyrrolyl group having 1 to 3 substituents independently selected from the group consisting of halo(C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ A substituted imidazolyl group having 1 to 2 substituents independently selected from the group consisting of alkoxy groups on the ring; (d58) A triazolyl group; (d59) A halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), an alkoxy group, a substituted triazolyl group having 1 substituent selected from the group consisting of alkoxy groups on the ring; (d60) A tetrazolyl group; (d61) A halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), an alkoxy group, a substituted tetrazolyl group having 1 substituent selected from the group consisting of alkoxy groups on the ring; (d62) An oxazolinyl group; (d63) A halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), an alkoxy group, a substituted oxazolinyl group having 1 to 4 substituents independently selected from the group consisting of alkoxy groups on the ring; (d64) A thiazolinyl group; (d65) A halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), an alkoxy group, a substituted thiazolinyl group having 1 to 4 substituents independently selected from the group consisting of alkoxy groups on the ring; (d66) An isoxazolinyl group; (d67) A halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), an alkoxy group, each independently selected from the group consisting of 1 to 4 substituents having a substituted isoxazolinyl group on the ring; (d68) an isothiazolinyl group; (d69) a halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), an alkoxy group, each independently selected from the group consisting of 1 to 4 substituents having a substituted isothiazolinyl group on the ring; (d70) a pyrrolidinyl group; (d71) a halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), an alkoxy group, each independently selected from the group consisting of 1 to 4 substituents having a substituted pyrrolidinyl group on the ring; (d72) an imidazolinyl group; (d73) a halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), an alkoxy group, each independently selected from the group consisting of 1 to 4 substituents having a substituted imidazolinyl group on the ring; (d95) an aminosulfonyl group; and (d96) N-(C １ -C ６ ), an alkylaminosulfonyl group, and The substituent group B is, (e1) cyano group; (e2) (C ３ -C ６ ) cycloalkyl group; (e3) (C １ -C ６ ) alkoxy group; (e4) (C １ -C ６ ) alkylthio group; (e5) (C １ -C ６ ) alkylsulfinyl group; (e6) (C １ -C ６ ) alkylsulfonyl group; (e7) halo(C ３ -C ６ ) cycloalkyl group; (e8) halo(C １ -C ６ ) alkoxy group; (e9) halo(C １ -C ６ ) alkylthio group; (e10) halo(C １ -C ６ ) alkylsulfinyl group; (e11) halo(C １ -C ６ ) alkylsulfonyl group; and (e12) (C １ -C ６ ) alkoxycarbonyl group, and The substituent group C is, (f1) Cyano group; (f2) (C １ -C ６ ) alkyl group; and (f10) halo(C １ -C ６ ) alkyl group, consisting of The substituent group D is, (g1) A halogen atom; (g2) A cyano group; (g3) A nitro group; (g7) (C １ -C ６ ) alkyl group; (g8) (C １ -C ６ ) alkoxy group; (g9) (C ３ -C ６ ) cycloalkyl group; (g10) (C １ -C ６ ) alkylthio group; (g11) (C １ -C ６ ) alkylsulfinyl group; (g12) (C １ -C ６ ) alkylsulfonyl group; (g13) Halo(C １ -C ６ ) alkyl group; (g14) Halo(C １ -C ６ ) alkoxy group; (g15) Halo(C ３ -C ６ ) cycloalkyl group; (g16) Halo(C １ -C ６ ) alkylthio group; (g17) Halo(C １ -C ６ ) alkylsulfinyl group; (g18) Halo(C １ -C ６ ) alkylsulfonyl group; (g23) A phenyl group; (g24) A halogen atom, a cyano group, (C １ -C ６ ) alkyl group, (C １ -C ６ ) alkoxy group, Halo(C １ [[ID=~58]]-C ６ ) alkyl group and Halo(C １ -C ６ ) alkoxy group, each independently selected from the group consisting of 1 to 5 substituents, having on the ring; and (g25) A methylenedioxy group optionally substituted with 1 to 2 substituents selected from the group consisting of a halogen atom, a phenyl group and (C １ -C ６ ) alkyl group, formed by two adjacent substituents together, the compound according to claim 1 or a salt thereof.

4. R １ is (a5) a phenyl group; (a6) a substituted phenyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (a7) a pyridyl group; (a8) a substituted pyridyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (a13) a pyrazinyl group; (a14) a substituted pyrazinyl group having 1 to 3 substituents independently selected from the substituent group A on the ring; (a99) a quinolinyl group; or (a100) a substituted quinolinyl group having 1 to 6 substituents independently selected from the substituent group A on the ring, R ２ is (b1) (C １ -C ６ ) alkyl group; (b4) (C ３ -C ６ ) cycloalkyl group; (b8) a substituted (C １ -C ６ ) alkyl group having 1 to 3 substituents independently selected from substituent group B; (b15) morpholinyl group; (b16) phenyl group; (b17) a substituted phenyl group having 1 to 5 substituents independently selected from substituent group D on the ring; (b18) pyridyl group; (b19) a substituted pyridyl group having 1 to 4 substituents independently selected from substituent group D on the ring; (b22) pyrimidinyl group; (b23) a substituted pyrimidinyl group having 1 to 3 substituents independently selected from substituent group D on the ring; (b32) isoxazolyl group; (b33) a substituted isoxazolyl group having 1 to 2 substituents independently selected from substituent group D on the ring; (b42) pyrazolyl group; or (b43) a substituted pyrazolyl group having 1 to 3 substituents independently selected from substituent group D on the ring, R ３ is a hydrogen atom, Y is an oxygen atom or a sulfur atom, Z is an oxygen atom, a sulfur atom, or a NOR ４ group (wherein R ４ represents a hydrogen atom.), and The substituent group A is, (d1) A halogen atom; (d2) A cyano group; (d6) (C １ -C ６ ) alkyl group; (d9) (C １ -C ６ ) alkoxy group; (d10) (C ３ -C ６ ) cycloalkyl group; (d12) (C １ -C ６ ) alkylsulfinyl group; (d13) (C １ -C ６ ) alkylsulfonyl group; (d14) Halo(C １ -C ６ ) alkyl group; (d17) Halo(C １ -C ６ ) alkoxy group; (d43) A halogen atom, a cyano group, (C １ -C ６ ) alkyl group, (C １ -C ６ ) alkoxy group, (C ３ -C ６ ) cycloalkyl group, Halo(C １ -C ６ ) alkyl group and Halo(C １ -C ６ ) alkoxy group, and having on the ring one substituent selected from the group consisting of; and (d95) an aminosulfonyl group, The substituent group B is, (e3) (C １ -C ６ ) alkoxy group; and (e4) (C １ -C ６ ) alkylthio group, consisting of The substituent group D is, (g1) A halogen atom; (g2) A cyano group; (g7) (C １ -C ６ ) alkyl group; (g8) (C １ -C ６ ) alkoxy group; (g10) (C １ -C ６ ) alkylthio group; (g13) Halo(C １ -C ６ ) alkyl group; (g14) Halo(C １ -C ６ ) alkoxy group; (g16) Halo(C １ -C ６ ) alkylthio group; and (g24) A halogen atom, a cyano group, (C １ -C ６ ) alkyl group, (C １ -C ６ ) alkoxy group, halo(C １ -C ６ ) alkyl group and halo(C １ -C ６ ) alkoxy group, each independently selected from the group consisting of 1 to 5 substituents, and having a substituted phenyl group having the substituents on the ring, the compound according to claim 1 or a salt thereof.

5. An insecticide characterized by containing, as an active ingredient, the compound or a salt thereof according to any one of Claims 1 to 4.

6. An insecticide for agricultural and horticultural use characterized by containing, as an active ingredient, the compound or a salt thereof according to any one of Claims 1 to 4.

7. A method for using an insecticide, characterized by treating a plant or soil with an effective amount of the insecticide according to Claim 5.

8. Use of the compound or a salt thereof according to any one of Claims 1 to 4 as an insecticide (excluding use for treating humans).

9. General formula (2) [Chemical 2] {In the formula,[[]] R １ is (a1) an aryl group; (a2) a substituted aryl group having one or more substituents independently selected from the substituent group A on the ring; (a3) a 5- to 10-membered heterocyclic group; or (a4) a substituted 5- to 10-membered heterocyclic group having one or more substituents independently selected from the substituent group A on the ring. R ７ is (h1) (C １ -C ６ ) alkyl group; or (h2) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group is shown. The substituent group A is, (d1) halogen atom; (d2) cyano group; (d3) nitro group; (d4) hydroxyl group; (d5) carboxyl group; (d6) (C １ -C ６ ) alkyl group; (d7) (C ２ -C ６ ) alkenyl group; (d8) (C ２ -C ６ ) alkynyl group; (d9) (C １ -C ６ ) alkoxy group; (d10) (C ３ -C ６ ) cycloalkyl group; (d11) (C １ -C ６ ) alkylthio group; (d12) (C １ -C ６ ) alkylsulfinyl group; (d13) (C １ -C ６ ) alkylsulfonyl group; (d14) halo(C １ -C ６ ) alkyl group; (d15) halo(C ２ -C ６ ) alkenyl group; (d16) halo(C ２ -C ６ ) alkynyl group; (d17) halo(C １ -C ６ ) alkoxy group; (d18) halo(C ３ -C ６ ) cycloalkyl group; (d19) halo(C １ -C ６ ) alkylthio group; (d^20) halo(C １ -C ６ ) alkylsulfinyl group; (d21) halo(C １ -C ６ ) alkylsulfonyl group; (d22) N,N-di(C １ -C ６ ) alkylaminosulfonyl group; (d23) halogen atom, cyano group, (C １ -C ６ ) alkyl group, (C １ -C ６ ) alkoxy group and (C １ -C ６ ), having on the ring from 1 to 3 substituents each independently selected from the group consisting of alkylcarbonyl groups ３ -C ６ ), cycloalkyl group; (d24) R ５ -(R ６ -N=)O=S group (wherein R ５ is a (C １ -C ６ alkyl group, a (C ３ -C ６ cycloalkyl group, halo(C １ -C ６ alkyl group, or a (C １ -C ６ alkoxy(C １ -C ６ alkyl group, and R ６ is a hydrogen atom, a cyano group, a (C １ -C ６ alkyl group, a (C ３ -C ６ cycloalkyl group, halo(C １ -C ６ alkyl group, a (C １ -C ６ alkylcarbonyl group, or a halo(C １ -C ６ alkylcarbonyl group.); (d25) SF ５ group; (d26) (C １ -C ６ alkoxy(C １ -C ６ alkyl group; (d27) (C １ -C ６ alkoxy(C １ -C ６ alkoxy group; (d28) (C １ -C ６ alkylcarbonylamino group; (d29) halo(C １ -C ６ alkylcarbonylamino group; (d30) (C １ -C ６ alkylsulfonylamino group; (d31) halo(C １ -C ６ alkylsulfonylamino group; (d32) (C １ -C ６ )an alkoxycarbonyl group; (d33) a methylenedioxy group which may be substituted with 1 to 2 substituents selected from the group consisting of a halogen atom, a phenyl group, and a (C １ -C ６ )alkyl group; (d34) an N-(C １ -C ６ )alkylaminocarbonyl group; (d35) an N-halo(C １ -C ６ )alkylaminocarbonyl group; (d36) a furanyl group; (d37) a halogen atom, a cyano group, a (C １ -C ６ )alkyl group, a (C １ -C ６ )alkoxy group, a halo(C １ -C ６ )alkyl group and a halo(C １ -C ６ )alkoxy group, and having 1 to 3 substituents independently selected from the group consisting of a substituted furanyl group on the ring; (d38) an oxazolyl group; (d39) a halogen atom, a cyano group, a (C １ -C ６ )alkyl group, a (C １ -C ６ )alkoxy group, a halo(C １ -C ６ )alkyl group and a halo(C １ -C ６ )alkoxy group, and having 1 to 2 substituents independently selected from the group consisting of a substituted oxazolyl group on the ring; (d40) an isoxazolyl group; (d41) a halogen atom, a cyano group, a (C １ -C ６ )alkyl group, a (C １ -C ６ )alkoxy group, a halo(C １ -C ６ )alkyl group and a halo(C １ -C ６ )alkoxy group, and having 1 to 2 substituents independently selected from the group consisting of a substituted isoxazolyl group on the ring; (d42) an oxadiazolyl group; (d43) a halogen atom, a cyano group, a (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, (C ３ -C ６ ), a cycloalkyl group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), an alkoxy group, having on the ring one substituent selected from the group consisting of; (d44) a thienyl group; (d45) a halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, (C ３ -C ６ ), a cycloalkyl group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), an alkoxy group, having on the ring one to three substituents each independently selected from the group consisting of; (d46) a thiazolyl group; (d47) a halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), an alkoxy group, having on the ring one to two substituents each independently selected from the group consisting of; (d48) an isothiazolyl group; (d49) a halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), an alkoxy group, having on the ring one to two substituents each independently selected from the group consisting of; (d50) a thiadiazolyl group; (d51) a halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), an alkoxy group; a substituted thiadiazolyl group having, on the ring, one substituent selected from the group consisting of halo(C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), an alkoxy group; a substituted pyrrolyl group having, on the ring, 1 to 3 substituents each independently selected from the group consisting of halo(C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), an alkoxy group; a substituted pyrazolyl group having, on the ring, 1 to 2 substituents each independently selected from the group consisting of halo(C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), an alkoxy group; a substituted imidazolyl group having, on the ring, 1 to 2 substituents each independently selected from the group consisting of halo(C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), a substituted triazolyl group having on the ring one substituent selected from the group consisting of an alkyl group and halo(C １ -C ６ ); (d60) a tetrazolyl group; (d61) a halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), an alkoxy group; a substituted tetrazolyl group having on the ring one substituent selected from the group consisting of a halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), an alkoxy group; a substituted oxazolinyl group having on the ring 1 to 4 substituents each independently selected from the group consisting of a halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), an alkoxy group; a substituted thiazolinyl group having on the ring 1 to 4 substituents each independently selected from the group consisting of a halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ A substituted isoxazolinyl group having 1 to 4 substituents independently selected from the group consisting of alkoxy groups on the ring; (d68) an isothiazolinyl group; (d69) a halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), an alkoxy group, having 1 to 4 substituents independently selected from the group consisting of substituted isothiazolinyl groups on the ring; (d70) a pyrrolidinyl group; (d71) a halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), an alkoxy group, having 1 to 4 substituents independently selected from the group consisting of substituted pyrrolidinyl groups on the ring; (d72) an imidazolinyl group; (d73) a halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), an alkoxy group, having 1 to 4 substituents independently selected from the group consisting of substituted imidazolinyl groups on the ring; (d74) a phenyl group; (d75) a halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, (C ３ -C ６ ), a cycloalkyl group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ A substituted phenyl group having 1 to 5 substituents independently selected from the group consisting of alkoxy groups on the ring; (d76) a pyridyl group; (d77) a halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group, and halo(C １ -C ６ ), a substituted pyridyl group having 1 to 4 substituents independently selected from the group consisting of an alkoxy group on the ring; (d78) a pyridazinyl group; (d79) a halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group, and halo(C １ -C ６ ), a substituted pyridazinyl group having 1 to 3 substituents independently selected from the group consisting of an alkoxy group on the ring; (d80) a pyrimidinyl group; (d81) a halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group, and halo(C １ -C ６ ), a substituted pyrimidinyl group having 1 to 3 substituents independently selected from the group consisting of an alkoxy group on the ring; (d82) a pyrazinyl group; (d83) a halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group, and halo(C １ -C ６ ), a substituted pyrazinyl group having 1 to 3 substituents independently selected from the group consisting of an alkoxy group on the ring; (d84) a triazinyl group; (d85) a halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group, and halo(C １ -C ６ A substituted triazinyl group having 1 to 2 substituents independently selected from the group consisting of alkoxy groups on the ring; (d86) Dihydrofuranyl group; (d87) Dihydropyranyl group; (d88) Phenyloxy group; (d89) Halogen atom, cyano group, (C １ -C ６ An alkyl group, (C １ -C ６ An alkoxy group, halo(C １ -C ６ An alkyl group and halo(C １ -C ６ A substituted phenyloxy group having 1 to 5 substituents independently selected from the group consisting of an alkoxy group on the ring; (d90) Phenyl(C １ -C ６ An alkoxy group; (d91) Halogen atom, cyano group, (C １ -C ６ An alkyl group, (C １ -C ６ An alkoxy group, halo(C １ -C ６ An alkyl group and halo(C １ -C ６ A substituted phenyl(C １ -C ６ An alkoxy group; (d92) Phenyl(C １ -C ６ An alkylthio group; (d93) Halogen atom, cyano group, (C １ -C ６ An alkyl group, (C １ -C ６ An alkoxy group, halo(C １ -C ６ An alkyl group and halo(C １ -C ６ A substituted phenyl(C １ -C ６ An alkylthio group; (d94) Tri(C １ -C ６ An alkylsilyl(C ２ -C ６ )alkynyl group; (d95) aminosulfonyl group; and (d96) N-(C １ -C ６ )consisting of an alkylaminosulfonyl group. However, R １ is a (C 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 ) alkylaminosulfonyl group, and R ５ -(R ６ -N=)O=S group (wherein R ５ is a (C １ -C ６ ) alkyl group, (C ３ -C ６ ) cycloalkyl group, halo(C １ -C ６ ) alkyl group, or (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, and R ６ is a hydrogen atom, cyano group, (C １ -C ６ ) alkyl group, (C ３ -C ６ ) cycloalkyl group, halo(C １ -C ６ ) alkyl group, (C １ -C ６ ) alkylcarbonyl group, or halo(C １ -C ６ ) alkylcarbonyl group. (The ) is not substituted.) A compound represented by {} or a salt thereof.

10. R ７ and the substituent group A is the same as in claim 9, R １ is (a5) phenyl group; (a6) a substituted phenyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a7) pyridyl group; (a8) a substituted pyridyl group having 1 to 4 substituents independently selected from the group of substituents A on the ring; (a9) pyridazinyl group; (a10) a substituted pyridazinyl group having 1 to 3 substituents independently selected from the group of substituents A on the ring; (a11) pyrimidinyl group; (a12) a substituted pyrimidinyl group having 1 to 3 substituents independently selected from the group of substituents A on the ring; (a13) pyrazinyl group; (a14) a substituted pyrazinyl group having 1 to 3 substituents independently selected from the group of substituents A on the ring; (a15) triazinyl group; (a16) a substituted triazinyl group having 1 to 2 substituents independently selected from the group of substituents A on the ring; (a17) 2-oxopyridyl group; (a18) a substituted 2-oxopyridyl group having 1 to 4 substituents independently selected from the group of substituents A on the ring; (a19) furanyl group; (a20) a substituted furanyl group having 1 to 3 substituents independently selected from the group of substituents A on the ring; (a21) oxazolyl group; (a22) a substituted oxazolyl group having 1 to 2 substituents independently selected from the group of substituents A on the ring; (a23) isoxazolyl group; (a24) a substituted isoxazolyl group having 1 to 2 substituents independently selected from the group of substituents A on the ring; (a25) oxadiazinyl group; (a26) a substituted oxadiazinyl group having 1 substituent selected from the group of substituents A on the ring; (a27) thienyl group; (a28) a substituted thienyl group having 1 to 3 substituents independently selected from the group of substituents A on the ring; (a29) thiazolyl group; (a30) a substituted thiazolyl group having 1 to 2 substituents independently selected from the group of substituents A on the ring; (a31) isothiazolyl group; (a32) a substituted isothiazolyl group having 1 to 2 substituents independently selected from the group of substituents A on the ring; (a33) thiadiazolyl group; (a34) a substituted thiadiazolyl group having 1 substituent selected from the group of substituents A on the ring; (a35) pyrrolyl group;(a36) A substituted pyrrolyl group having 1 to 4 substituents independently selected from the group of substituents A on the ring; (a37) A pyrazolyl group; (a38) A substituted pyrazolyl group having 1 to 3 substituents independently selected from the group of substituents A on the ring; (a39) An imidazolyl group; (a40) A substituted imidazolyl group having 1 to 3 substituents independently selected from the group of substituents A on the ring; (a41) A triazolyl group; (a42) A substituted triazolyl group having 1 to 2 substituents independently selected from the group of substituents A on the ring; (a43) A tetrazolyl group; (a44) A substituted tetrazolyl group having 1 substituent selected from the group of substituents A on the ring; (a45) A benzofuranyl group; (a46) A substituted benzofuranyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a47) A benzoxazolyl group; (a48) A substituted benzoxazolyl group having 1 to 4 substituents independently selected from the group of substituents A on the ring; (a49) A benzisoxazolyl group; (a50) A substituted benzisoxazolyl group having 1 to 4 substituents independently selected from the group of substituents A on the ring; (a51) A benzothienyl group; (a52) A substituted benzothienyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a53) A benzothiazolyl group; (a54) A substituted benzothiazolyl group having 1 to 4 substituents independently selected from the group of substituents A on the ring; (a55) A benzisothiazolyl group; (a56) A substituted benzisothiazolyl group having 1 to 4 substituents independently selected from the group of substituents A on the ring; (a57) An indolyl group; (a58) A substituted indolyl group having 1 to 6 substituents independently selected from the group of substituents A on the ring; (a59) An isoindolyl group; (a60) A substituted isoindolyl group having 1 to 6 substituents independently selected from the group of substituents A on the ring; (a61) An indazolyl group; (a62) A substituted indazolyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a63) A benzimidazolyl group; (a64) A substituted benzimidazolyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring;(a65) a benzotriazolyl group; (a66) a substituted benzotriazolyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (a67) a furopyridyl group; (a68) a substituted furopyridyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (a69) a thienopyridyl group; (a70) a substituted thienopyridyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (a71) a thiazolopyridyl group; (a72) a substituted thiazolopyridyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (a73) an imidazopyridyl group; (a74) a substituted imidazopyridyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (a75) an indolizinyl group; (a76) a substituted indolizinyl group having 1 to 6 substituents independently selected from the substituent group A on the ring; (a77) a pyrrolopyridyl group; (a78) a substituted pyrrolopyridyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (a79) a pyrrolopyrimidinyl group; (a80) a substituted pyrrolopyrimidinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (a81) an oxazolopyridyl group; (a82) a substituted oxazolopyridyl group having 1 to 3 substituents independently selected from the substituent group A on the ring; (a83) an isoxazolopyridyl group; (a84) a substituted isoxazolopyridyl group having 1 to 3 substituents independently selected from the substituent group A on the ring; (a85) an isothiazolopyridyl group; (a86) a substituted isothiazolopyridyl group having 1 to 3 substituents independently selected from the substituent group A on the ring; (a87) an imidazopyrimidinyl group; (a88) a substituted imidazopyrimidinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (a89) a pyrazolopyridyl group; (a90) a substituted pyrazolopyridyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (a91) a pyrazolopyrimidinyl group; (a92) a substituted pyrazolopyrimidinyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (a93) a triazolopyridyl group;(a94) A substituted triazolopyridyl group having 1 to 4 substituents independently selected from the group of substituents A on the ring; (a95) A triazolopyrimidinyl group; (a96) A substituted triazolopyrimidinyl group having 1 to 4 substituents independently selected from the group of substituents A on the ring; (a97) A quinoxalinyl group; (a98) A substituted quinoxalinyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a99) A quinolinyl group; (a100) A substituted quinolinyl group having 1 to 6 substituents independently selected from the group of substituents A on the ring; (a101) A naphthyl group; (a102) A substituted naphthyl group having 1 to 7 substituents independently selected from the group of substituents A on the ring; (a103) An isoquinolinyl group; (a104) A substituted isoquinolinyl group having 1 to 6 substituents independently selected from the group of substituents A on the ring; (a105) A cinnolinyl group; (a106) A substituted cinnolinyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a107) A phthalazinyl group; (a108) A substituted phthalazinyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a109) A quinazolinyl group; (a110) A substituted quinazolinyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a111) A naphthyridinyl group; or (a112) A substituted naphthyridinyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring, the compound according to claim 9 or a salt thereof.;

11. R １ is (a5) phenyl group; (a6) a substituted phenyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a7) pyridyl group; (a8) a substituted pyridyl group having 1 to 4 substituents independently selected from the group of substituents A on the ring; (a9) pyridazinyl group; (a10) a substituted pyridazinyl group having 1 to 3 substituents independently selected from the group of substituents A on the ring; (a11) pyrimidinyl group; (a12) a substituted pyrimidinyl group having 1 to 3 substituents independently selected from the group of substituents A on the ring; (a13) pyrazinyl group; (a14) a substituted pyrazinyl group having 1 to 3 substituents independently selected from the group of substituents A on the ring; (a15) triazinyl group; (a16) a substituted triazinyl group having 1 to 2 substituents independently selected from the group of substituents A on the ring; (a17) 2-oxopyridyl group; (a18) a substituted 2-oxopyridyl group having 1 to 4 substituents independently selected from the group of substituents A on the ring; (a27) thienyl group; (a28) a substituted thienyl group having 1 to 3 substituents independently selected from the group of substituents A on the ring; (a97) quinoxalinyl group; (a98) a substituted quinoxalinyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a99) quinolinyl group; (a100) a substituted quinolinyl group having 1 to 6 substituents independently selected from the group of substituents A on the ring; (a101) naphthyl group; (a102) a substituted naphthyl group having 1 to 7 substituents independently selected from the group of substituents A on the ring; (a103) isoquinolinyl group; (a104) a substituted isoquinolinyl group having 1 to 6 substituents independently selected from the group of substituents A on the ring; (a105) cinnolinyl group; (a106) a substituted cinnolinyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a107) phthalazinyl group; (a108) a substituted phthalazinyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a109) quinazolinyl group; (a110) a substituted quinazolinyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a111) naphthyridinyl group;or a substituted naphthyridinyl group having from 1 to 5 substituents independently selected from the group A on the ring; R ７ is (h1) (C １ -C ６ ) alkyl group; or (h2) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, The substituent group A is, (d1) A halogen atom; (d2) A cyano group; (d6) (C １ -C ６ -) An alkyl group; (d7) (C ２ -C ６ -) An alkenyl group; (d8) (C ２ -C ６ -) An alkynyl group; (d9) (C １ -C ６ -) An alkoxy group; (d10) (C ３ -C ６ -) A cycloalkyl group; (d11) (C １ -C ６ -) An alkylthio group; (d12) (C １ -C ６ -) An alkylsulfinyl group; (d13) (C １ -C ６ -) An alkylsulfonyl group; (d14) Halo(C １ -C ６ -) An alkyl group; (d15) Halo(C ２ -C ６ -) An alkenyl group; (d16) Halo(C ２ -C ６ -) An alkynyl group; (d17) Halo(C １ -C ６ -) An alkoxy group; (d18) Halo(C ３ -C ６ -) A cycloalkyl group; (d19) Halo(C １ -C ６ -) An alkylthio group; (d20) Halo(C １ -C ６ -) An alkylsulfinyl group; (d21) Halo(C １ -C ６ -) An alkylsulfonyl group; (d22) N,N-Di(C １ -C ６ -) An alkylaminosulfonyl group; (d23) A halogen atom, a cyano group, (C １ -C ６ -) An alkyl group, (C １ -C ６ -) An alkoxy group and (C １ -C ６ -) An alkylcarbonyl group, each independently selected from the group consisting of 1 to 3 substituents having on the ring a substituted (C ３ -C ６ ), cycloalkyl group; (d26) (C １ -C ６ ), alkoxy (C １ -C ６ ), alkyl group; (d27) (C １ -C ６ ), alkoxy (C １ -C ６ ), alkoxy group; (d32) (C １ -C ６ ), alkoxycarbonyl group; (d33) A methylenedioxy group optionally substituted with 1 to 2 substituents selected from the group consisting of a halogen atom, a phenyl group, and an (C １ -C ６ ), alkyl group; (d36) furanyl group; (d37) a halogen atom, a cyano group, an (C １ -C ６ ), alkyl group, an (C １ -C ６ ), alkoxy group, halo(C １ -C ６ ), alkyl group, and halo(C １ -C ６ ), alkoxy group; A substituted furanyl group having 1 to 3 substituents independently selected from the group on the ring; (d38) oxazolyl group; (d39) a halogen atom, a cyano group, an (C １ -C ６ ), alkyl group, an (C １ -C ６ ), alkoxy group, halo(C １ -C ６ ), alkyl group, and halo(C １ -C ６ ), alkoxy group; A substituted oxazolyl group having 1 to 2 substituents independently selected from the group on the ring; (d40) isoxazolyl group; (d41) a halogen atom, a cyano group, an (C １ -C ６ ), alkyl group, an (C １ -C ６ ), alkoxy group, halo(C １ -C ６ ), alkyl group, and halo(C １ -C ６ A substituted isoxazolyl group having 1 to 2 substituents independently selected from the group consisting of alkoxy groups on the ring; (d42) an oxadiazolyl group; (d43) a halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, (C ３ -C ６ ), a cycloalkyl group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), an alkoxy group, a substituted oxadiazolyl group having 1 substituent selected from the group consisting of alkoxy groups on the ring; (d52) a pyrrolyl group; (d53) a halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), an alkoxy group, a substituted pyrrolyl group having 1 to 3 substituents independently selected from the group consisting of alkoxy groups on the ring; (d54) a pyrazolyl group; (d55) a halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), an alkoxy group, a substituted pyrazolyl group having 1 to 2 substituents independently selected from the group consisting of alkoxy groups on the ring; (d56) an imidazolyl group; (d57) a halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ A substituted imidazolyl group having 1 to 2 substituents independently selected from the group consisting of alkoxy groups on the ring; (d58) A triazolyl group; (d59) A halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), an alkoxy group; a substituted triazolyl group having 1 substituent selected from the group consisting of the above on the ring; (d60) A tetrazolyl group; (d61) A halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), an alkoxy group; a substituted tetrazolyl group having 1 substituent selected from the group consisting of the above on the ring; (d62) An oxazolinyl group; (d63) A halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), an alkoxy group; a substituted oxazolinyl group having 1 to 4 substituents independently selected from the group consisting of the above on the ring; (d64) A thiazolinyl group; (d65) A halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), an alkoxy group; a substituted thiazolinyl group having 1 to 4 substituents independently selected from the group consisting of the above on the ring; (d66) An isoxazolinyl group; (d67) A halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), an alkoxy group, each independently selected from the group consisting of 1 to 4 substituents having a substituted isoxazolinyl group on the ring; (d68) an isothiazolinyl group; (d69) a halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), an alkoxy group, each independently selected from the group consisting of 1 to 4 substituents having a substituted isothiazolinyl group on the ring; (d70) a pyrrolidinyl group; (d71) a halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), an alkoxy group, each independently selected from the group consisting of 1 to 4 substituents having a substituted pyrrolidinyl group on the ring; (d72) an imidazolinyl group; (d73) a halogen atom, a cyano group, (C １ -C ６ ), an alkyl group, (C １ -C ６ ), an alkoxy group, halo(C １ -C ６ ), an alkyl group and halo(C １ -C ６ ), an alkoxy group, each independently selected from the group consisting of 1 to 4 substituents having a substituted imidazolinyl group on the ring; (d95) an aminosulfonyl group; and (d96) N-(C １ -C ６ ), an alkylaminosulfonyl group, a compound according to claim 9 or 10 or a salt thereof.

12. R １ is (a5) phenyl group; (a6) a substituted phenyl group having 1 to 5 substituents independently selected from the group of substituents A on the ring; (a7) pyridyl group; (a8) a substituted pyridyl group having 1 to 4 substituents independently selected from the group of substituents A on the ring; (a13) pyrazinyl group; (a14) a substituted pyrazinyl group having 1 to 3 substituents independently selected from the group of substituents A on the ring; (a99) quinolinyl group; or (a100) a substituted quinolinyl group having 1 to 6 substituents independently selected from the group of substituents A on the ring, R ７ is a (h1) (C １ -C ６ ) alkyl group, wherein the group of substituents A is (d1) A halogen atom; (d2) A cyano group; (d6) (C １ -C ６ ) An alkyl group; (d9) (C １ -C ６ ) An alkoxy group; (d10) (C ３ -C ６ ) A cycloalkyl group; (d11) (C １ -C ６ ) An alkylthio group; (d12) (C １ -C ６ ) An alkylsulfinyl group; (d13) (C １ -C ６ ) An alkylsulfonyl group; (d14) Halo(C １ -C ６ ) An alkyl group; (d17) Halo(C １ -C ６ ) An alkoxy group; (d43) A halogen atom, a cyano group, (C １ -C ６ ) An alkyl group, (C １ -C ６ ) An alkoxy group, (C ３ -C ６ ) A cycloalkyl group, halo(C １ -C ６ ) An alkyl group and halo(C １ -C ６ ) An alkoxy group having one substituent selected from the group consisting of a substituted oxadiazolyl group having on the ring; (d61) A halogen atom, a cyano group, (C １ -C ６ ) An alkyl group, (C １ -C ６ ) An alkoxy group, halo(C １ -C ６ ) An alkyl group and halo(C １ -C ６ ) An alkoxy group having one substituent selected from the group consisting of a substituted tetrazolyl group having on the ring; and (d95) An aminosulfonyl group, a compound according to claim 9 or 10 or a salt thereof.

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