JP2012056903A - Pyridazinone compound, and herbicide and noxious arthropod controlling agent containing the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a compound having an excellent weed-controlling effect and an excellent noxious arthropod-controlling effect.SOLUTION: The pyridazinone compound represented by formula (I) is useful as active constituents of herbicides and noxious arthropod controlling agents. In the formula: Ris hydrogen, a 1-6C alkyl group or the like; Ris hydrogen, halogen or the like; Ris hydrogen or a 1-6C alkyl group; Wis oxygen or sulfur; Wis halogen or the like; G is a 5- or 6-membered heteroaromatic ring; and J is a benzene ring or a 5- or 6-membered heteroaromatic ring.

Description

  The present invention relates to pyridazinone compounds and herbicides and harmful arthropod control agents containing the same.

Until now, the development of compounds as active ingredients of herbicides for controlling weeds has been widely promoted, and compounds having the effect of controlling weeds have been found.
Various compounds have been studied and put into practical use for the purpose of controlling harmful arthropods.
A pyridazinone compound having herbicidal activity (see Patent Document 1) is known.

WO2009 / 086041

  An object of the present invention is to provide a compound having an excellent weed control effect and a compound having an excellent control effect against pests.

（式中、
Ｒ¹は水素、Ｃ_1-6アルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6アルキニル基、Ｃ_1-6ハロアルキル基、Ｃ_2-6ハロアルケニル基、Ｃ_2-6ハロアルキニル基、Ｃ_3-8シクロアルキル基、Ｃ_3-8ハロシクロアルキル基、Ｃ_4-10アルキルシクロアルキル基、Ｃ_4-10シクロアルキルアルキル基、Ｃ_6-14シクロアルキルシクロアルキル基、Ｃ_4-10ハロシクロアルキルアルキル基、Ｃ_5-12アルキルシクロアルキルアルキル基、Ｃ_3-8シクロアルケニル基、Ｃ_3-8ハロシクロアルケニル基、Ｃ_2-8アルコキシアルキル基、Ｃ_4-10シクロアルコキシアルキル基、Ｃ_3-10アルコキシアルコキシアルキル基、Ｃ_2-8アルキルチオアルキル基、Ｃ_2-8アルキルスルフィニルアルキル基、Ｃ_2-8アルキルスルホニルアルキル基又はテトラヒドロピラニル基を表し、
Ｒ²は水素、ハロゲン、シアノ基、-Ｃ(＝Ｏ）ＯＨ、-Ｃ(＝Ｏ）ＮＨ₂、Ｃ_1-6アルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6アルキニル基、Ｃ_1-6ハロアルキル基、Ｃ_2-6ハロアルケニル基、Ｃ_2-6ハロアルキニル基、Ｃ_3-8シクロアルキル基、Ｃ_3-8ハロシクロアルキル基、Ｃ_4-10アルキルシクロアルキル基、Ｃ_4-10シクロアルキルアルキル基、Ｃ_6-14シクロアルキルシクロアルキル基、Ｃ_4-10ハロシクロアルキルアルキル基、Ｃ_5-12アルキルシクロアルキルアルキル基、Ｃ_3-8シクロアルケニル基、Ｃ_3-8ハロシクロアルケニル基、Ｃ_2-8アルコキシアルキル基、Ｃ_4-10シクロアルコキシアルキル基、Ｃ_3-10アルコキシアルコキシアルキル基、Ｃ_2-8アルキルチオアルキル基、Ｃ_2-8アルキルスルフィニルアルキル基、Ｃ_2-8アルキルスルホニルアルキル基、Ｃ_2-8アルコキシカルボニル基、Ｃ_4-10シクロアルコキシカルボニル基、Ｃ_5-12シクロアルキルアルコキシカルボニル基、Ｃ_2-8アルキルアミノカルボニル基、Ｃ_3-10ジアルキルアミノカルボニル基、Ｃ_4-10シクロアルキルアミノカルボニル基、Ｃ_1-6アルコキシ基、Ｃ_1-6ハロアルコキシ基、Ｃ_1-6アルキルチオ基、Ｃ_1-6ハロアルキルチオ基、ニトロ基、Ｃ_3-6シクロアルコキシ基又はＣ_4-8シクロアルキルアルコキシ基を表し、
Ｒ³は水素又はＣ_1-6アルキル基を表し、
Ｗ¹は酸素又は硫黄を表し、
Ｗ²はハロゲン又は下記式

｛式中、Ｒ⁴、Ｒ⁵、Ｒ⁷、及びＲ¹¹はＣ_1-6アルキル基、Ｃ_3-8シクロアルキル基、
Ｃ_3-6アルケニル基、Ｃ_3-6アルキニル基、フェニル基又はフェニルＣ_1-6アルキル基を表し、
Ｒ¹²は、Ｃ_1-6アルキル基、Ｃ_3-8シクロアルキル基、Ｃ_3-6アルケニル基、Ｃ_3-6アルキニル基、フェニル基又はフェニルＣ_1-6アルキル基を表し、
Ｒ⁶、Ｒ⁸、及びＲ⁹は、Ｃ_1-6アルキル基、Ｃ_3-8シクロアルキル基、Ｃ_3-6アルケニル基、Ｃ_3-6アルキニル基、フェニル基、フェニルＣ_1-6アルキル基、Ｃ_1-6アルコキシ基、Ｃ_3-8シクロアルキルオキシ基、Ｃ_3-6アルケニルオキシ基、Ｃ_3-6アルキニルオキシ基、フェノキシ基又はフェニルＣ_1-6アルコキシ基を表し、
Ｒ¹⁰は、Ｃ_1-6アルキル基、Ｃ_3-8シクロアルキル基、Ｃ_3-6アルケニル基、Ｃ_3-6アルキニル基、フェニル基、フェニルＣ_1-6アルキル基、Ｃ_1-6アルコキシ基、Ｃ_3-8シクロアルキルオキシ基、Ｃ_3-6アルケニルオキシ基、Ｃ_3-6アルキニルオキシ基、フェノキシ基又はフェニルＣ_1-6アルコキシ基を表し、又はＲ⁹及びＲ¹⁰は結合するカルボニル基及び窒素と一緒になってベンゼン環が縮合していてもよい５若しくは６員の環状イミド基を表し、
ここで、Ｒ⁴、Ｒ⁵、Ｒ⁶、Ｒ⁷、Ｒ⁸、Ｒ⁹、Ｒ¹⁰、Ｒ¹¹及びＲ¹²で表されるいずれの基もハロゲン及びＣ_1-6アルコキシ基からなる群より選ばれる少なくとも一個で置換されていてもよく、
Ｒ⁴、Ｒ⁵、Ｒ⁶、Ｒ⁷、Ｒ⁸、Ｒ⁹、Ｒ¹⁰、Ｒ¹¹及びＲ¹²で表されるフェニル基、及びフェニルＣ_1-6アルキル基のフェニル部分は、いずれもＣ_1-6アルキル基により置換されていてもよく、
Ｒ⁶、Ｒ⁸、Ｒ⁹及びＲ¹⁰で表されるフェノキシ基、及びフェニルＣ_1-6アルコキシ基のフェニル部分は、いずれもＣ_1-6アルキル基により置換されていてもよく、
ｍは０、１または２を表す。}で示される基を表し、
Ｇは５もしくは６員環の複素芳香環（尚、該複素芳香環がその構成要素として窒素を１以上含む場合、該窒素はそれぞれＲ^xで置換されていてもよい。また、該複素芳香環の構成要素である炭素はＲ^wから独立して選ばれた最大４置換基で置換されていてもよい。）を表し、
Ｊはベンゼン環又は５もしくは６員環の複素芳香環（尚、該ベンゼン環および該複素芳香環はＲ^uから独立して選ばれた最大５置換基で置換されていてもよい。）を表し、
Ｒ^uはそれぞれ独立してハロゲン、シアノ基、ヒドロキシ基、アミノ基、ニトロ基、-ＣＨＯ、-Ｃ（＝Ｏ）ＯＨ、-Ｃ（＝Ｏ）ＮＨ₂、-ＳＯ₂ＮＨ₂、ＳＦ₅、Ｃ_1-6アルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6アルキニル基、Ｃ_1-6ハロアルキル基、Ｃ_3-8シクロアルキル基、Ｃ_3-8ハロシクロアルキル基、Ｃ_4-10アルキルシクロアルキル基、Ｃ_4-10シクロアルキルアルキル基、Ｃ_4-10ハロシクロアルキルアルキル基、Ｃ_5-12アルキルシクロアルキルアルキル基、Ｃ_2-8アルキルカルボニル基、Ｃ_2-8ハロアルキルカルボニル基、Ｃ_2-8アルコキシカルボニル基、Ｃ_4-10シクロアルコキシカルボニル基、Ｃ_5-12シクロアルキルアルコキシカルボニル基、Ｃ_2-8アルキルアミノカルボニル基、Ｃ_3-10ジアルキルアミノカルボニル基、Ｃ_1-6アルコキシ基、Ｃ_1-6ハロアルコキシ基、Ｃ_2-8アルキルカルボニルオキシ基、Ｃ_1-6アルキルチオ基、Ｃ_1-6ハロアルキルチオ基、Ｃ_1-6アルキルスルフィニル基、Ｃ_1-6ハロアルキルスルフィニル基、Ｃ_1-6アルキルスルホニル基、Ｃ_1-6ハロアルキルスルホニル基、Ｃ_1-6アルキルアミノスルホニル基、Ｃ_2-8ジアルキルアミノスルホニル基、Ｃ_3-10トリアルキルシリル基、Ｃ_1-6アルキルアミノ基、Ｃ_2-8ジアルキルアミノ基、Ｃ_2-8アルキルカルボニルアミノ基、Ｃ_1-6アルキルスルホニルアミノ基、フェニル基、ピリジニル基又はチエニル基を表し、
Ｒ^wはそれぞれ独立してハロゲン、シアノ基、ヒドロキシ基、アミノ基、ニトロ基、-ＣＨＯ、-Ｃ（＝Ｏ）ＯＨ、-Ｃ（＝Ｏ）ＮＨ₂、-ＳＯ₂ＮＨ₂、ＳＦ₅、Ｃ_1-6アルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6アルキニル基、Ｃ_1-6ハロアルキル基、Ｃ_3-8シクロアルキル基、Ｃ_3-8ハロシクロアルキル基、Ｃ_4-10アルキルシクロアルキル基、Ｃ_4-10シクロアルキルアルキル基、Ｃ_4-10ハロシクロアルキルアルキル基、Ｃ_5-12アルキルシクロアルキルアルキル基、Ｃ_2-8アルキルカルボニル基、Ｃ_2-8ハロアルキルカルボニル基、Ｃ_2-8アルコキシカルボニル基、Ｃ_4-10シクロアルコキシカルボニル基、Ｃ_5-12シクロアルキルアルコキシカルボニル基、Ｃ_2-8アルキルアミノカルボニル基、Ｃ_3-10ジアルキルアミノカルボニル基、Ｃ_1-6アルコキシ基、Ｃ_1-6ハロアルコキシ基、Ｃ_2-8アルキルカルボニルオキシ基、Ｃ_1-6アルキルチオ基、Ｃ_1-6ハロアルキルチオ基、Ｃ_1-6アルキルスルフィニル基、Ｃ_1-6ハロアルキルスルフィニル基、Ｃ_1-6アルキルスルホニル基、Ｃ_1-6ハロアルキルスルホニル基、Ｃ_1-6アルキルアミノスルホニル基、Ｃ_2-8ジアルキルアミノスルホニル基、Ｃ_3-10トリアルキルシリル基、Ｃ_1-6アルキルアミノ基、Ｃ_2-8ジアルキルアミノ基、Ｃ_2-8アルキルカルボニルアミノ基、Ｃ_1-6アルキルスルホニルアミノ基又はナフチル基を表し、
Ｒ^xはそれぞれ独立してＣ_1-3アルキル基またはＣ_3-7シクロアルキル基を表す。）

で示されるピリダジノン化合物（以下、本発明化合物と記す。）、
本発明化合物を有効成分として含有する除草剤、
本発明化合物の有効量を雑草又は雑草の生育する土壌に施用する雑草の防除方法、
雑草又は雑草の生育する土壌に施用して雑草を防除するための本発明化合物の使用、
本発明化合物を有効成分として含有する有害節足動物防除剤、
本発明化合物の有効量を有害節足動物又は有害節足動物の生息場所に施用する有害節足動物の防除方法、
有害節足動物を防除するための本発明化合物の使用、および
除草剤又は有害節足動物防除剤の製造のための本発明化合物の使用
を提供する。 As a result of intensive studies, the present inventor has found that the pyridazinone compound represented by the formula (I) has an excellent weed control effect and an excellent control effect against pests, and has reached the present invention.
That is, the present invention provides a compound of formula (I)

(Where
R ¹ is hydrogen, C _1-6 alkyl groups, C _2-6 alkenyl groups, C _2-6 alkynyl, C _1-6 haloalkyl groups, C _2-6 haloalkenyl groups, C _2-6 haloalkynyl groups, C _3-8 cycloalkyl group, C _3-8 halocycloalkyl group, C _4-10 alkyl cycloalkyl group, C _4-10 cycloalkylalkyl group, C _6-14 cycloalkyl cycloalkyl group, C _4-10 halocyclo group _Alkylalkyl group, C _5-12 alkylcycloalkylalkyl group, C _3-8 cycloalkenyl group, C _3-8 halocycloalkenyl group, C _2-8 alkoxyalkyl group, C _4-10 cycloalkoxyalkyl group, C _{3 -10 represents an} alkoxyalkoxyalkyl group, a _C2-8 alkylthioalkyl group, a _C2-8 alkylsulfinylalkyl group, a _C2-8 alkylsulfonylalkyl group or a tetrahydropyranyl group,
R ² is hydrogen, halogen, cyano group, —C (═O) OH, —C (═O) NH ₂ , C _1-6 alkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _{1 -6} haloalkyl group, C _2-6 haloalkenyl group, C _2-6 haloalkynyl group, C _3-8 cycloalkyl group, C _3-8 halocycloalkyl group, C _4-10 alkylcycloalkyl group, C _{4- 10} cycloalkylalkyl group, C _6-14 cycloalkylcycloalkyl group, C _4-10 halocycloalkylalkyl group, C _5-12 alkylcycloalkylalkyl group, C _3-8 cycloalkenyl group, C _3-8 halocyclo Alkenyl group, C _2-8 alkoxyalkyl group, C _4-10 cycloalkoxyalkyl group, C _3-10 alkoxyalkoxyalkyl group, C _2-8 alkylthioalkyl group, C _2-8 alkylsulfinylalkyl group, C _2-8 alkylsulfonyl group, C _2-8 A Job aryloxycarbonyl group, C _4-10 cycloalkoxy group, C _5-12 cycloalkyl alkoxycarbonyl group, C _2-8 alkylaminocarbonyl group, C _3-10 dialkylamino group, C _4-10 cycloalkyl aminocarbonyl Group, C _1-6 alkoxy group, C _1-6 haloalkoxy group, C _1-6 alkylthio group, C _1-6 haloalkylthio group, nitro group, C _3-6 cycloalkoxy group or C _4-8 cycloalkylalkoxy Represents a group,
R ³ represents hydrogen or a C _1-6 alkyl group,
W ¹ represents oxygen or sulfur,
W ² is halogen or the following formula

{Wherein R ⁴ , R ⁵ , R ⁷ , and R ¹¹ are a C _1-6 alkyl group, a C _3-8 cycloalkyl group,
A C _3-6 alkenyl group, a C _3-6 alkynyl group, a phenyl group or a phenyl C _1-6 alkyl group;
R ¹² represents a C _1-6 alkyl group, a C _3-8 cycloalkyl group, a C _3-6 alkenyl group, a C _3-6 alkynyl group, a phenyl group or a phenyl C _1-6 alkyl group,
R ⁶ , R ⁸ , and R ⁹ are a C _1-6 alkyl group, a C _3-8 cycloalkyl group, a C _3-6 alkenyl group, a C _3-6 alkynyl group, a phenyl group, a phenyl C _1-6 alkyl group. A C _1-6 alkoxy group, a C _3-8 cycloalkyloxy group, a C _3-6 alkenyloxy group, a C _3-6 alkynyloxy group, a phenoxy group or a phenyl C _1-6 alkoxy group,
R ¹⁰ represents a C _1-6 alkyl group, a C _3-8 cycloalkyl group, a C _3-6 alkenyl group, a C _3-6 alkynyl group, a phenyl group, a phenyl C _1-6 alkyl group, a C _1-6 alkoxy group. _Represents a C _3-8 cycloalkyloxy group, a C _3-6 alkenyloxy group, a C _3-6 alkynyloxy group, a phenoxy group or a phenyl C _1-6 alkoxy group, or R ⁹ and R ¹⁰ are bonded carbonyl groups. And a 5- or 6-membered cyclic imide group that may be condensed with a benzene ring together with nitrogen,
Here, any group represented by R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ and R ¹² is selected from the group consisting of halogen and C _1-6 alkoxy groups. May be substituted with at least one
The phenyl group represented by R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ and R ¹² and the phenyl moiety of the phenyl C _1-6 alkyl group are all C _{1. Optionally} substituted by a _-6 alkyl group,
Any of the phenoxy group represented by R ⁶ , R ⁸ , R ⁹ and R ¹⁰ and the phenyl moiety of the phenyl C _1-6 alkoxy group may be substituted with a C _1-6 alkyl group,
m represents 0, 1 or 2; } Represents a group represented by
G is a 5- or 6-membered heteroaromatic ring (in the case where the heteroaromatic ring contains at least one nitrogen as a constituent element, the nitrogen may each be substituted with R ^x . The carbon which is a constituent of the above may be substituted with a maximum of 4 substituents independently selected from R ^w ),
J represents a heteroaromatic ring of benzene ring or a 5- or 6-membered ring (Incidentally, the benzene ring and the complex-aromatic ring may be substituted with up to 5 substituents independently selected from R ^u.) ,
Each R ^u is independently halogen, cyano group, hydroxy group, amino group, nitro group, —CHO, —C (═O) OH, —C (═O) NH ₂ , —SO ₂ NH ₂ , SF ₅ , C _1-6 alkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _1-6 haloalkyl group, C _3-8 cycloalkyl group, C _3-8 halocycloalkyl group, C _4-10 alkyl Cycloalkyl group, C _4-10 cycloalkylalkyl group, C _4-10 halocycloalkylalkyl group, C _5-12 alkylcycloalkylalkyl group, C _2-8 alkylcarbonyl group, C _2-8 haloalkylcarbonyl group, C _2-8 alkoxycarbonyl group, C _4-10 cycloalkoxycarbonyl group, C _5-12 cycloalkylalkoxycarbonyl group, C _2-8 alkylaminocarbonyl group, C _3-10 dialkylaminocarbonyl group, C _1-6 alkoxy group , C _1-6 Haroa Kokishi group, C _2-8 alkylcarbonyloxy, C _1-6 alkylthio group, C _1-6 haloalkylthio group, C _1-6 alkylsulfinyl group, C _1-6 haloalkylsulfinyl group, C _1-6 alkylsulfonyl group C _1-6 haloalkylsulfonyl group, C _1-6 alkylaminosulfonyl group, C _2-8 dialkylaminosulfonyl group, C _3-10 trialkylsilyl group, C _1-6 alkylamino group, C _2-8 dialkylamino Group, C _2-8 alkylcarbonylamino group, C _1-6 alkylsulfonylamino group, phenyl group, pyridinyl group or thienyl group,
R ^w is independently halogen, cyano group, hydroxy group, amino group, nitro group, —CHO, —C (═O) OH, —C (═O) NH ₂ , —SO ₂ NH ₂ , SF ₅ , C _1-6 alkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _1-6 haloalkyl group, C _3-8 cycloalkyl group, C _3-8 halocycloalkyl group, C _4-10 alkyl Cycloalkyl group, C _4-10 cycloalkylalkyl group, C _4-10 halocycloalkylalkyl group, C _5-12 alkylcycloalkylalkyl group, C _2-8 alkylcarbonyl group, C _2-8 haloalkylcarbonyl group, C _2-8 alkoxycarbonyl group, C _4-10 cycloalkoxycarbonyl group, C _5-12 cycloalkylalkoxycarbonyl group, C _2-8 alkylaminocarbonyl group, C _3-10 dialkylaminocarbonyl group, C _1-6 alkoxy group , C _1-6 Haroa Kokishi group, C _2-8 alkylcarbonyloxy, C _1-6 alkylthio group, C _1-6 haloalkylthio group, C _1-6 alkylsulfinyl group, C _1-6 haloalkylsulfinyl group, C _1-6 alkylsulfonyl group C _1-6 haloalkylsulfonyl group, C _1-6 alkylaminosulfonyl group, C _2-8 dialkylaminosulfonyl group, C _3-10 trialkylsilyl group, C _1-6 alkylamino group, C _2-8 dialkylamino A group, a C _2-8 alkylcarbonylamino group, a C _1-6 alkylsulfonylamino group or a naphthyl group,
Each R ^x independently represents a C _1-3 alkyl group or a C _3-7 cycloalkyl group. )

A pyridazinone compound represented by the following (hereinafter referred to as the present compound),
A herbicide containing the compound of the present invention as an active ingredient,
A method for controlling weeds, wherein an effective amount of the compound of the present invention is applied to weeds or a soil where weeds grow;
Use of the compound of the present invention for controlling weeds by applying to weeds or soil where weeds grow,
A harmful arthropod control agent comprising the compound of the present invention as an active ingredient,
A method for controlling harmful arthropods, which comprises applying an effective amount of the compound of the present invention to harmful arthropods or habitats of harmful arthropods,
There is provided the use of a compound of the present invention for controlling harmful arthropods, and the use of a compound of the present invention for the production of a herbicide or a harmful arthropod control agent.

  The compound of the present invention has the effect of controlling weeds and harmful arthropods.

In the present invention, the meanings of the substituents are as follows.
The C _1-6 alkyl group means an alkyl group having 1 to 6 carbon atoms, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group. , Pentyl group, sec-pentyl group, isopentyl group, neopentyl group, hexyl group and isohexyl group.
The C _2-6 alkenyl group means an alkenyl group having 2 to 6 carbon atoms, and examples thereof include a vinyl group, an allyl group, a 1-buten-3-yl group, and a 3-buten-1-yl group.
The C _2-6 alkynyl group means an alkynyl group having 2 to 6 carbon atoms, and examples thereof include an ethynyl group, a propargyl group, and a 2-butynyl group.
The C _3-6 alkenyl group means an alkenyl group having 3 to 6 carbon atoms, and examples thereof include an allyl group, a 1-buten-3-yl group, and a 3-buten-1-yl group.
The C _3-6 alkynyl group means an alkynyl group having 3 to 6 carbon atoms, and examples thereof include a propargyl group and a 2-butynyl group.
The C _1-6 haloalkyl group means a haloalkyl group having 1 to 6 carbon atoms, and examples thereof include F ₃ C— group, ClCH ₂ —, CF ₃ CH ₂ —, and CF ₃ CCl ₂ — group.
The C _2-6 haloalkenyl group means a haloalkenyl group having 2 to 6 carbon atoms, and examples thereof include a (Cl) ₂ C═CHCH ₂ — group and a CF ₃ CH ₂ CH═CHCH ₂ — group.
The C _2-6 haloalkynyl group means a haloalkynyl group having 2 to 6 carbon atoms, such as HC≡CCHCl— group, CF ₃ C≡C— group, CCl ₃ C≡C— group and FCH ₂ C. ≡CCH _2- .

The C _3-8 cycloalkyl group means a cycloalkyl group having 3 to 8 carbon atoms, and examples thereof include a cyclopropyl group, a cyclopentyl group, and a cyclohexyl group.
The C _3-8 halocycloalkyl group means a halocycloalkyl group having 3 to 8 carbon atoms, and examples thereof include a 2-chlorocyclopropyl group and a 4,4-difluorocyclohexyl group.
The C _4-10 alkylcycloalkyl group means an alkylcycloalkyl group having 4 to 10 carbon atoms, and examples thereof include an ethylcyclopropyl group, an isobutylcyclopropyl group, a 3-methylcyclopentyl group, and a 4-methylcyclohexyl group. It is done.
The C _4-10 cycloalkylalkyl group means a cycloalkylalkyl group having 4 to 10 carbon atoms, and examples thereof include a cyclopropylmethyl group and a cyclopentylmethyl group.
The C _6-14 cycloalkylcycloalkyl group means a cycloalkylcycloalkyl group having 6 to 14 carbon atoms, and examples thereof include a 2-cyclopropylcyclopropyl group and a 3-cyclopropylcyclopentyl group.
The C _4-10 halocycloalkylalkyl group means a halocycloalkylalkyl group having 4 to 10 carbon atoms, and examples thereof include a 2-chlorocyclopropylmethyl group and a 3-chlorocyclopentylethyl group.
The C _5-12 alkylcycloalkylalkyl group means an alkylcycloalkylalkyl group having 5 to 12 carbon atoms, and examples thereof include a 2-methylcyclopropylmethyl group and a 3-methylcyclopentylmethyl group.
The C _3-8 cycloalkenyl group means a cycloalkenyl group having 3 to 8 carbon atoms, and examples thereof include a 2-cyclopentenyl group, a 1-cyclohexenyl group, a 1,3-cyclohexadienyl group, and a 1,4- A cyclohexadienyl group is mentioned.
The C _3-8 halocycloalkenyl group means a halocycloalkenyl group having 3 to 8 carbon atoms, and examples thereof include a 2-chloro-1-cyclopentenyl group and a 2-chloro-1-cyclohexenyl group.

The C _2-8 alkoxyalkyl group means an alkoxyalkyl group having 2 to 8 carbon atoms, such as a CH ₃ OCH ₂ — group, a CH ₃ OCH ₂ CH ₂ — group, a CH ₃ CH ₂ OCH ₂ — group, _{CH 3 CH 2 CH 2 CHOCH 2} - group and _{CH 3 CH 2 OCH 2 CH 2} - group.
The C _4-10 cycloalkoxyalkyl group means a C _4-10 cycloalkoxyalkyl group, and examples thereof include a cyclopropyloxymethyl group and a cyclopentyloxymethyl group.
The C _3-10 alkoxyalkoxyalkyl group means an alkoxyalkoxyalkyl group having 3 to 10 carbon atoms, such as a CH ₃ OCH ₂ OCH ₂ — group, a CH ₃ CH ₂ O (CH ₃ ) CHOCH ₂ — group, and (CH ₃ O) ₂ CHOCH ₂ — group.
The C _2-8 alkylthioalkyl group means an alkylthioalkyl group having 2 to 8 carbon atoms, such as a CH ₃ SCH ₂ — group, a CH ₃ SCH ₂ CH ₂ — group, a CH ₃ CH ₂ SCH ₂ — group, CH ₃ CH ₂ CH ₂ CH ₂ SCH ₂ — group and CH ₃ CH ₂ SCH ₂ CH ₂ — group may be mentioned.
The C _2-8 alkylsulfinylalkyl group means an alkylsulfinylalkyl group having 2 to 8 carbon atoms, for example, a CH ₃ S (O) CH ₂ — group, a CH ₃ S (O) CH ₂ CH ₂ — group. CH ₃ CH ₂ S (O) CH ₂ — group, CH ₃ CH ₂ CH ₂ CH ₂ S (O) CH ₂ — group and CH ₃ CH ₂ S (O) CH ₂ CH ₂ — group.
The C _2-8 alkylsulfonylalkyl group means an alkylsulfonylalkyl group having 2 to 8 carbon atoms, for example, CH ₃ S (O) ₂ CH ₂ — group, CH ₃ S (O) ₂ CH ₂ CH _2. - _{group, CH 3 CH 2 S (O} ) 2 CH 2 - _{group, CH 3 CH 2 CH 2 CH} 2 S (O) 2 CH 2 - group and _{CH 3 CH 2 S (O)} 2 CH 2 CH 2 - group Is mentioned.

The C _2-8 alkoxycarbonyl group means an alkoxycarbonyl group having 2 to 8 carbon atoms, for example, a CH ₃ OC (═O) — group, a CH ₃ CH ₂ OC (═O) — group, a CH ₃ CH ₂ CH ₂ OC (═O) — group and (CH ₃ ) ₂ CHOC (═O) — group.
The C _4-10 cycloalkoxycarbonyl group means a cycloalkoxycarbonyl group having 4 to 10 carbon atoms, and examples thereof include a cyclopropyloxycarbonyl group and a cyclopentyloxycarbonyl group.
The C _5-12 cycloalkylalkoxycarbonyl group means a cycloalkylalkoxycarbonyl group having 5 to 12 carbon atoms, and examples thereof include a cyclopropylmethyloxycarbonyl-group and a cyclopentylmethyloxycarbonyl-group.
The C _2-8 alkylaminocarbonyl group means an alkylaminocarbonyl group having 2 to 8 carbon atoms, such as a CH ₃ NHC (═O) — group, a CH ₃ CH ₂ NHC (═O) — group, and ( CH ₃ ) ₃ CNHC (═O) — group.
The C _3-10 dialkylaminocarbonyl group means a C _3-10 dialkylaminocarbonyl group, for example, a (CH ₃ ) ₂ NC (═O) — group and a (CH ₃ CH ₂ ) ₂ NC (= O) -groups.
The C _4-10 cycloalkylaminocarbonyl group means a cycloalkylaminocarbonyl group having 4 to 10 carbon atoms, and examples thereof include an N-cyclopropylcarbamoyl group and an N-cyclopentylcarbamoyl group.

The C _1-6 alkoxy group means an alkoxy group having 1 to 6 carbon atoms. For example, a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, an isobutoxy group, a sec-butoxy group, a tert- Examples include butoxy group, pentoxy group, sec-pentoxy group, isopentoxy group, neopentoxy group, hexyloxy group and isohexyloxy group.
The C _1-6 haloalkoxy group means a haloalkoxy group having 1 to 6 carbon atoms, for example, F ₃ CO— group, CCl ₃ CH ₂ O—, HCF ₂ CH ₂ CH ₂ O— and CF ₃ CH ₂ O-group.
The C _1-6 alkylthio group means an alkylthio group having 1 to 6 carbon atoms, and examples thereof include a CH ₃ S— group, a CH ₃ CH ₂ S— group, and a (CH ₃ ) ₃ CS— group.
The C _1-6 haloalkylthio group means a haloalkylthio group having 1 to 6 carbon atoms, such as CCl ₃ S— group, CF ₃ S—, CCl ₃ CH ₂ S— and ClCH ₂ CH ₂ CH ₂ S. -Groups.
The C _3-6 cycloalkoxy group means a C _3-6 cycloalkoxy group, and examples thereof include a cyclopropyloxy group, a cyclopentyloxy group, and cyclohexyloxy.
The C _4-8 cycloalkylalkoxy group means a cycloalkylalkoxy group having 4 to 8 carbon atoms, such as a cyclopropyl-CH ₂ O— group, a cyclopropyl-CH (CH ₃ ) O— group, and a cyclopentyl- CH ₂ O— group.
The phenyl C _1-6 alkyl group means a phenyl C _1-6 alkyl group having 1 to 6 carbon atoms in the alkyl group, and examples thereof include a phenylmethyl group, a phenylethyl group, and a phenylpropyl group.
The C _3-8 cycloalkyloxy group means a cycloalkyloxy group having 3 to 8 carbon atoms, and examples thereof include a cyclopropyloxy group, a cyclopentyloxy group, and a cyclohexyloxy group.
The C _3-6 alkenyloxy group means an alkenyloxy group having 3 to 6 carbon atoms, and examples thereof include an allyloxy group and a 3-butenyloxy group.
The C _3-6 alkynyloxy group means an alkynyloxy group having 3 to 6 carbon atoms, and examples thereof include a propargyloxy group and a 2-butynyloxy group.
The phenyl C _1-6 alkoxy group means a phenylalkoxy group having 1 to 6 carbon atoms in the alkoxy group, and examples thereof include a phenylmethoxy group, a phenylethoxy group, and a phenylpropyloxy group.

The C _2-8 alkylcarbonyl group means an alkylcarbonyl group having 2 to 8 carbon atoms. For example, a CH ₃ C (═O) — group, a CH ₃ CH ₂ C (═O) — group, a CH ₃ CH ₂ CH ₂ C (═O) — group and (CH ₃ ) ₂ CHC (═O) — group.
The C _2-8 haloalkylcarbonyl group means a haloalkylcarbonyl group having 2 to 8 carbon atoms, for example, a ClCH ₂ C (═O) — group, a CF ₃ C (═O) — group, and a (CF ₃ ) _2. And CHC (= O)-group.
The C _2-8 alkylcarbonyloxy group means an alkylcarbonyloxy group having 2 to 8 carbon atoms, such as a CH ₃ C (═O) O— group, a CH ₃ CH ₂ C (═O) O— group. , CH ₃ CH ₂ CH ₂ C (═O) O— group and (CH ₃ ) ₂ CHC (═O) O— group.
The C _1-6 alkylsulfinyl group means an alkylsulfinyl group having 1 to 6 carbon atoms, such as a CH ₃ S (O) — group, a CH ₃ CH ₂ S (O) — group, and a (CH ₃ ) ₃ group. And CS (O) -group.
The C _1-6 haloalkylsulfinyl group means a haloalkylsulfinyl group having 1 to 6 carbon atoms, such as a CCl ₃ S (O) — group, a CF ₃ S (O) — group, a CCl ₃ CH ₂ S (O )-Group and ClCH ₂ CH ₂ CH ₂ S (O)-group.
The C _1-6 alkylsulfonyl group means an alkylsulfonyl group having 1 to 6 carbon atoms, and examples thereof include a CH ₃ S (O) ₂ — group, a CH ₃ CH ₂ S (O) ₂ — group, and a (CH ₃ ) ₃ CS (O) ₂ -group.
The C _1-6 haloalkylsulfonyl group means a haloalkylsulfonyl group having 1 to 6 carbon atoms, for example, a CCl ₃ S (O) ₂ — group, a CF ₃ S (O) ₂ — group, a CCl ₃ CH ₂ S (O) ₂ -group and ClCH ₂ CH ₂ CH ₂ S (O) ₂ -group.
The C _1-6 alkylaminosulfonyl group means an alkylaminosulfonyl group having 1 to 6 carbon atoms, such as a CH ₃ NHS (O) ₂ — group, a CH ₃ CH ₂ NHS (O) ₂ — group, and ( CH ₃ ) ₃ CNHS (O) ₂ — group.
The C _2-8 dialkylaminosulfonyl group means a dialkylaminosulfonyl group having 2 to 8 carbon atoms, for example, a (CH ₃ ) ₂ NS (O) ₂ — group and a (CH ₃ CH ₂ ) ₂ NS (O ) ₂ -group.

The C _3-10 trialkylsilyl group means a trialkylsilyl group having 3 to 10 carbon atoms, such as a (CH ₃ ) ₃ Si— group, a (CH ₃ CH ₂ ) ₃ Si— group, and a (CH ₃ ) group. ) ₃ C (CH ₃ ) ₂ Si— group.
The C _1-6 alkylamino group means an alkylamino group having 1 to 6 carbon atoms, and examples thereof include a CH ₃ NH— group, a CH ₃ CH ₂ NH— group, and a (CH ₃ ) ₃ CNH— group. .
The C _2-8 dialkylamino group means a dialkylamino group having 2 to 8 carbon atoms, and examples thereof include a (CH ₃ ) ₂ N— group and a (CH ₃ CH ₂ ) ₂ N— group.
The C _2-8 alkylcarbonylamino group means an alkylcarbonylamino group having 2 to 8 carbon atoms, such as a CH ₃ C (═O) NH— group, a CH ₃ CH ₂ C (═O) NH— group. , CH ₃ CH ₂ CH ₂ C (═O) NH— group and (CH ₃ ) ₂ CHC (═O) NH— group.
The C _1-6 alkylsulfonylamino group means an alkylsulfonylamino group having 1 to 6 carbon atoms, such as a CH ₃ S (O) ₂ NH— group, a CH ₃ CH ₂ S (O) ₂ NH— group. And (CH ₃ ) ₃ CS (O) ₂ NH— group.
Examples of the halogen include fluorine, chlorine, bromine and iodine.

Examples of the 5- or 6-membered cyclic imide group in which the benzene ring may be condensed together with the carbonyl group and nitrogen to which R ⁹ and R ¹⁰ are bonded include, for example, succinimide group, glutarimide group, maleimide group and phthalimide Groups.

The 5- or 6-membered heteroaromatic ring represented by G means an aromatic 5- or 6-membered heterocyclic group containing 1 to 3 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur. And when the ring contains nitrogen, the nitrogen may be substituted with R ^x , the carbon may be substituted with up to 4 substituents independently selected from R ^w , and the heterocycle is pyridazinone When the ring contains nitrogen and the ring contains nitrogen, the bond may come out from the nitrogen, for example, imidazole, thiophene, furan, pyrrole, triazole, isothiazole, isoxazole, pyrazole Oxazole, thiazole, pyridine, pyridazine, pyrimidine, pyrazine and triazine.

The heteroaromatic ring a benzene ring or a 5- or 6-membered ring represented by J, may be substituted with up to 5 substituents independently selected from R ^u, for example, include groups such as It is done.
Here, r represents 0 or 1, and the bond on the left of the ring is the bond with G.

  In the compound of the present invention, the pyridazinone compound represented by the formula (I) may take the form of an agriculturally acceptable salt with an inorganic base or an organic base, but the present invention also includes a pyridazinone compound in the form of the salt. Is included. Examples of such salts include inorganic bases (eg, alkali metal (lithium, sodium, potassium, etc.) hydroxides, carbonates, hydrogen carbonates, acetates, hydrides, alkaline earth metals (magnesium, calcium, Hydroxide), hydride, etc., ammonia), organic bases (eg, dimethylamine, triethylamine, piperazine, pyrrolidine, piperidine, 2-phenylethylamine, benzylamine, ethanolamine, diethanolamine, pyridine, collidine, etc.), Examples thereof include salts formed by mixing with metal alkoxides (for example, sodium methoxide, potassium tert-butoxide, magnesium methoxide and the like).

When the compound of the present invention has one or more asymmetric centers, the compound has two or more stereoisomers (for example, enantiomers, diastereomers, etc.). The compound of the present invention includes all of these stereoisomers and a mixture of any two or more thereof.
When the compound of the present invention has geometric isomerism based on a double bond or the like, the compound contains two or more geometric isomers (for example, E / Z or trans / cis isomers, S-trans / S-cis). Each isomer) and the like. The compounds of the present invention include all of these geometric isomers and mixtures of any two or more thereof.

As this invention compound, the compound shown below is mentioned, for example.
[1] In the formula (I), R ¹ is hydrogen, a C _1-6 alkyl group, a C _2-6 alkenyl group, a C _2-6 alkynyl group, a C _1-6 haloalkyl group, a C _2-6 haloalkenyl group, C _2-6 haloalkynyl group, C _3-8 cycloalkyl group, C _3-8 halocycloalkyl group, C _4-10 alkylcycloalkyl group, C _4-10 cycloalkylalkyl group, C _6-14 cycloalkylcyclo Alkyl group, C _4-10 halocycloalkylalkyl group, C _5-12 alkylcycloalkylalkyl group, C _3-8 cycloalkenyl group, C _3-8 halocycloalkenyl group, C _2-8 alkoxyalkyl group, C _{4 A} compound which is a _-10 cycloalkoxyalkyl group, a C _3-10 alkoxyalkoxyalkyl group, a C _2-8 alkylthioalkyl group, a C _2-8 alkylsulfinylalkyl group or a C _2-8 alkylsulfonylalkyl group,

[2] In [1], R ¹ is hydrogen, C _1-6 alkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _1-6 haloalkyl group, C _2-6 haloalkenyl group, C 2 _2-6 haloalkynyl group, C _3-8 cycloalkyl group, C _3-8 halocycloalkyl group, C _4-10 alkylcycloalkyl group, C _4-10 cycloalkylalkyl group, C _6-14 cycloalkylcycloalkyl group, C _4-10 halocycloalkyl group, C _5-12 alkylcycloalkyl group, C _2-8 alkoxyalkyl group, C _4-10 compound cycloalkyl alkoxyalkyl group or C _3-10 alkoxyalkoxy group ,
[3] A compound in which R ¹ is hydrogen, a C _1-6 alkyl group, a C _1-6 haloalkyl group or a C _3-8 cycloalkyl group in [2],
[4] The compound according to [3], wherein R ¹ is hydrogen or a C _1-6 alkyl group,
[5] In [4], a compound wherein R ¹ is a methyl group,

[6] The compound according to [3], wherein R ¹ is a C _1-6 haloalkyl group,
[7] The compound according to [3], wherein R ¹ is a C _3-8 cycloalkyl group,
[8] A compound in which R ¹ is a tetrahydropyranyl group in the formula (I),
[9] In the formula (I) or [1] to [8], R ² is hydrogen, halogen, cyano group, —C (═O) OH, —C (═O) NH ₂ , C _1-6 alkyl group C _2-6 alkenyl group, C _2-6 alkynyl group, C _1-6 haloalkyl group, C _2-6 haloalkenyl group, C _2-6 haloalkynyl group, C _3-8 cycloalkyl group, C _3-8 Halocycloalkyl group, C _4-10 alkylcycloalkyl group, C _4-10 cycloalkylalkyl group, C _6-14 cycloalkylcycloalkyl group, C _4-10 halocycloalkylalkyl group, C _5-12 alkylcycloalkyl Alkyl group, C _3-8 cycloalkenyl group, C _3-8 halocycloalkenyl group, C _2-8 alkoxyalkyl group, C _4-10 cycloalkoxyalkyl group, C _3-10 alkoxyalkoxyalkyl group, C _2-8 alkylthioalkyl group, C _2-8 alkylsulfinyl group, C _2-8 Le Kill sulfonyl group, C _2-8 alkoxycarbonyl group, C _4-10 cycloalkoxy group, C _5-12 cycloalkyl alkoxycarbonyl group, C _2-8 alkylaminocarbonyl group, C _3-10 dialkylamino group, A compound having a C _4-10 cycloalkylaminocarbonyl group, a C _1-6 alkoxy group, a C _1-6 haloalkoxy group, a C _1-6 alkylthio group or a C _1-6 haloalkylthio group,
[10] In [9], R ² is hydrogen, halogen, C _1-6 alkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _1-6 haloalkyl group, C _3-8 cycloalkyl group C _3-8 halocycloalkyl group, C _4-10 alkylcycloalkyl group, C _4-10 cycloalkylalkyl group, C _6-14 cycloalkylcycloalkyl group, C _4-10 halocycloalkylalkyl group, C _{5 -12} alkyl cycloalkyl alkyl group, C _3-8 cycloalkenyl group, C _3-8 halocycloalkenyl group, C _2-8 alkoxyalkyl group, C _2-8 alkoxycarbonyl group, C _1-6 alkoxy group, C _{1 A} compound which is a _-6 haloalkoxy group or a C _1-6 alkylthio group,

[11] In [10], R ² is hydrogen, halogen, C _1-6 alkyl group, C _1-6 haloalkyl group, C _3-8 cycloalkyl group, C _2-8 alkoxyalkyl group, C _1-4 alkoxy A compound that is a group,
[12] The compound according to [11], wherein R ² is hydrogen, halogen, a C _1-6 alkyl group or a C _1-4 alkoxy group,
[13] In [12], a compound wherein R ² is hydrogen, chlorine, a methyl group, an ethyl group or a methoxy group,
[14] The compound according to [9], wherein R ² is hydrogen, halogen, C _1-6 alkyl group, C _1-6 haloalkyl group, C _3-8 cycloalkyl group or C _2-8 alkoxyalkyl group,
[15] The compound according to [14], wherein R ² is hydrogen, halogen or a C _1-6 alkyl group,

[16] In [15], a compound wherein R ² is hydrogen, chlorine, a methyl group or an ethyl group,
[17] The compound according to [13] or [16], wherein R ² is hydrogen,
[18] The compound according to [13] or [16], wherein R ² is chlorine;
[19] The compound according to [13] or [16], wherein R ² is a methyl group,
[20] A compound in which in formula (I) or [1] to [19], R ³ is hydrogen, a methyl group or an ethyl group,

[21] In [20], a compound in which R ³ is hydrogen,
[22] A compound in which W ² is OR ⁴ in formula (I) or [1] to [21],
[23] In the compound [22], wherein R ⁴ is a C _1-6 alkyl group, a C _3-8 cycloalkyl group, a C _3-6 alkenyl group, a C _3-6 alkynyl group or a phenyl group,
[24] The compound according to [23], wherein R ⁴ is a C _1-6 alkyl group,
[25] In [24], a compound wherein R ⁴ is a methyl group or an ethyl group,

[26] A compound in which W ² is —S (O) _m —R ⁵ in formula (I) or [1] to [21],
[27] In [26], a compound wherein m is 0, 1 or 2, and R ⁵ is a C _1-6 alkyl group,
[28] In [27], a compound wherein m is 0, 1 or 2, and R ⁵ is a methyl group or an ethyl group,
[29] A compound in which W ² is —OCOR ⁶ in the formula (I) or [1] to [21],
[30] In [29], a compound wherein R ⁶ is a C _1-6 alkyl group, a C _3-6 alkenyl group, a C _3-6 alkynyl group or a phenyl group,

で示される基である化合物、
[３５] [３４]において、Ｒ⁷がＣ_1-6アルキル基である化合物、 [31] In the compound [30], wherein R ⁶ is a C _1-6 alkyl group, a C _3-6 alkenyl group, or a C _3-6 alkynyl group,
[32] In [31], a compound wherein R ⁶ is a methyl group, an ethyl group, an allyl group or a propargyl group,
[33] In [32], a compound wherein R ⁶ is a methyl group or an ethyl group,
[34] In the compound represented by the formula (I) or [1] to [21], W ² represents the formula

A compound which is a group represented by:
[35] In [34], a compound wherein R ⁷ is a C _1-6 alkyl group,

[36] In [35], a compound wherein R ⁷ is a methyl group or an ethyl group,
[37] [34], wherein R ⁸ is a C _1-6 alkyl group, a C _3-6 alkenyl group, a C _3-6 alkynyl group or a phenyl group,
[38] The compound according to [37], wherein R ⁸ is a C _1-6 alkyl group, a C _3-6 alkenyl group, or a C _3-6 alkynyl group,
[39] In [38], a compound wherein R ⁸ is a methyl group, an ethyl group, an allyl group or a propargyl group,
[40] In [39], a compound wherein R ⁸ is a methyl group or an ethyl group,

で示される基である化合物、
[４２] [４１]において、Ｒ⁹がＣ_1-6アルキル基、Ｃ_3-6アルケニル基、Ｃ_3-6アルキニル基又はフェニル基である化合物、
[４３] [４２]において、Ｒ⁹がＣ_1-6アルキル基、Ｃ_3-6アルケニル基又はＣ_3-6アルキニル基である化合物、
[４４] [４３]において、Ｒ⁹がメチル基、エチル基、アリル基又はプロパルギル基である化合物、
[４５] [４４]において、Ｒ⁹がメチル基又はエチル基である化合物、 [41] In the compound represented by the formula (I) or [1] to [21], W ² represents the formula

A compound which is a group represented by:
[42] [41], wherein R ⁹ is a C _1-6 alkyl group, a C _3-6 alkenyl group, a C _3-6 alkynyl group or a phenyl group,
[43] In [42], a compound wherein R ⁹ is a C _1-6 alkyl group, a C _3-6 alkenyl group or a C _3-6 alkynyl group,
[44] In [43], a compound wherein R ⁹ is a methyl group, an ethyl group, an allyl group or a propargyl group,
[45] In [44], a compound wherein R ⁹ is a methyl group or an ethyl group,

で示される基である化合物、 [46] The compound according to [41], wherein R ¹⁰ is a C _1-6 alkyl group, a C _3-6 alkenyl group, a C _3-6 alkynyl group or a phenyl group,
[47] The compound according to [46], wherein R ¹⁰ is a C _1-6 alkyl group, a C _3-6 alkenyl group or a C _3-6 alkynyl group,
[48] In [47], a compound wherein R ¹⁰ is a methyl group, an ethyl group, an allyl group or a propargyl group,
[49] In [48], a compound wherein R ¹⁰ is a methyl group or an ethyl group,
[50] In the compound represented by the formula (I) or [1] to [21], W ² represents the formula

A compound which is a group represented by:

[51] In [50], a compound wherein R ¹¹ is a C _1-6 alkyl group,
[52] In [51], a compound wherein R ¹¹ is a methyl group or an ethyl group,
[53] The compound according to [50], wherein R ¹² is a C _1-6 alkyl group, a C _3-8 cycloalkyl group, a C _3-6 alkenyl group, a C _3-6 alkynyl group or a phenyl group,
[54] In [53], a compound wherein R ¹² is a C _1-6 alkyl group,
[55] In [54], a compound wherein R ¹² is a methyl group or an ethyl group,

（ここで、環の左の結合は式（Ｉ）のピリダジノン環との結合であり、右の結合はJとの結合であり、ｔは０または１、ｘは０、１または２を表し、Ｒ^XおよびＲ^Wは前記と同じ意味を表す。） [56] A compound represented by the formula (I) or a compound represented by [1] to [55], wherein G is a ring selected from the following G-1 to G-69:

(Wherein the bond on the left of the ring is a bond with the pyridazinone ring of formula (I), the bond on the right is with J, t is 0 or 1, x represents 0, 1 or 2, R ^X and R ^W represent the same meaning as described above.)

[57] A compound in which in the formula (I) or [1] to [56], each R ^x is independently hydrogen or a C _1-3 alkyl group,
[58] In [57], a compound in which G is bonded to other than the 2-position of J and G,
[59] In [58], a compound in which G is bonded to J and G at the 3-position or 4-position,
[60] In [56] to [59], G is G-3 to G-6, G-9 to G-18, G-22 to G-31, G-33 to G-35, G-39 to A compound which is a ring selected from G-45, G-48, G-50, G-53 to G-57, G-59 to G-62 or G-65 to G-68,

[61] The compound according to [60], wherein G is a ring selected from G-12 to G-15, G-26, G-28, G-29, G-34, G-35 or G-62;
[62] The compound in [61], wherein G is a ring selected from G-12, G-15, G-26, G-28, G-29, G-34, G-35 or G-62,
[63] A compound in which x is 1 in [56] to [62],
[64] In [56] to [62], a compound in which x is 2;
[65] The compound according to [56] to [62], wherein at least one R ^w is adjacent to the bond between G and the pyridazinone ring,

[66] In [56] to [62], a compound wherein G is G-26,
[67] In [56] to [62] or [66], a compound in which x is 1 and R ^w is bonded to the 5-position of G-26,
[68] In [56] to [62] or [66], a compound in which x is 2 and R ^w is bonded to the 4th and 5th positions of G-26,
[69] The compound in [56] to [62], wherein G is G-15,
[70] The compound according to [56] to [62], wherein G is G-29,

[71] In [56] to [62], a compound in which G is G-28, x is 1, and R ^w is bonded to the 2-position of G-28;
[72] [56] to [62], wherein G is G-28, x is 2, and R ^w is bonded to the 2-position and 5-position of G-28,
[73] In [56] to [60], a compound wherein G is G-45,
[74] In [56] to [62], a compound in which G is G-62, x is 1, and R ^w is bonded to the 5-position of G-62;
[75] In [56] to [62], a compound in which G is G-35, x is 1, and R ^w is bonded to the 4-position of G-35;

[76] In [56] to [62], a compound in which G is G-34, x is 1, and R ^w is bonded to the 3-position of G-34;
[77] In [56] to [62], a compound wherein G is G-12,
[78] In the compound represented by the formula (I) or [1] to [77], each R ^w is independently halogen, cyano group, hydroxy group, amino group, nitro group, —CHO, —C (═O ) OH, SF ₅ , C _1-6 alkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _1-6 haloalkyl group, C _3-8 cycloalkyl group, C _3-8 halocycloalkyl group C _4-10 alkylcycloalkyl group, C _4-10 cycloalkylalkyl group, C _4-10 halocycloalkylalkyl group, C _5-12 alkylcycloalkylalkyl group, C _2-8 alkylcarbonyl group, C _{2- 8} haloalkylcarbonyl group, C _2-8 alkoxycarbonyl group, C _2-8 alkylaminocarbonyl group, C _3-10 dialkylamino group, C _1-6 alkoxy, C _1-6 haloalkoxy group, C _2-8 alkylcarbonyloxy, C _1-6 alkyl Thio, C _1-6 alkylsulfonyl group, C _1-6 haloalkylsulfonyl group, C _1-6 alkylaminosulfonyl group, C _2-8 dialkylamino sulfonyl group, C _1-6 alkylamino group, C _2-8 dialkyl A compound which is an amino group, a C _2-8 alkylcarbonylamino group, a C _1-6 alkylsulfonylamino group or a naphthyl group,
[79] In [78], each R ^w is independently halogen, hydroxy group, C _1-6 alkyl group, C _1-6 haloalkyl group, C _3-8 cycloalkyl group, C _1-6 alkoxy group or C A compound that is a _1-6 haloalkoxy group,
[80] In [79], each R ^w is independently halogen, C _1-6 alkyl group, C _1-6 haloalkyl group, C _3-8 cycloalkyl group, C _1-6 alkoxy group or C _1-6. A compound which is a haloalkoxy group,

[81] The compound according to [80], wherein each R ^w is independently a halogen or a C _1-6 alkyl group,
[82] The compound according to [81], wherein each R ^w is independently halogen, methyl group, ethyl group or n-propyl group,
[83] In [82], compounds wherein R ^w is independently a halogen, a methyl group or an ethyl group,
[84] In [83], compounds wherein R ^w is each independently a methyl group or an ethyl group,
In [85] compound or [1] represented by (I) ~ [84], J is a heteroaromatic ring of benzene ring or a 5 or 6-membered ring, the ring is independently selected from R ^u Compounds substituted with up to 3 substituents,

[86] In [85], J is a heteroaromatic ring of benzene ring or a 6-membered ring, compounds whose ring is substituted with up to 3 substituents independently selected from R ^u.
In [87] [86], J is a benzene ring, compounds whose ring is substituted with up to 3 substituents independently selected from R ^u,
[88] In [87], J is a benzene ring, compounds whose ring is substituted with substituents independently selected from R ^u,
In [89] [88], J is a benzene ring, the compound 4-position of the ring is substituted with substituents independently selected from R ^u,
[90] In the compound represented by formula (I) or [1] to [89], J is a benzene ring, and the 3-position, 4-position or 5-position of the ring is substituted with a halogen or a C _1-6 haloalkyl group A compound comprising

[91] In the compound represented by the formula (I) or [1] to [90], each R ^u is independently halogen, cyano group, hydroxy group, amino group, nitro group, —CHO, —C (═O ) OH, —C (═O) NH ₂ , —SO ₂ NH ₂ , SF ₅ , C _1-6 alkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _1-6 haloalkyl group, C _3-8 cycloalkyl group, C _3-8 halocycloalkyl group, C _2-8 alkylcarbonyl group, C _2-8 haloalkylcarbonyl group, C _2-8 alkoxycarbonyl group, C _2-8 alkylaminocarbonyl group, C _3-10 dialkylaminocarbonyl group, C _1-6 alkoxy group, C _1-6 haloalkoxy group, C _2-8 alkylcarbonyloxy group, C _1-6 alkylthio group, C _1-6 haloalkylthio group, C _{1- 6} alkylsulfonyl group, C _1-6 haloalkylsulfonyl group, C _1-6 alkyl Minosuruhoniru group, C _2-8 dialkylamino sulfonyl group, C _1-6 alkylamino group, C _2-8 dialkylamino group, C _2-8 alkylcarbonylamino group, C _1-6 alkylsulfonylamino group, a phenyl group, A compound which is a pyridinyl group or a thienyl group,
[92] In [91], each R ^u is independently halogen, cyano group, nitro group, —CHO, —C (═O) OH, C _1-6 alkyl group, C _1-6 haloalkyl group, C _{3. -8} cycloalkyl group, C _3-8 halocycloalkyl group, C _1-6 alkoxy group, C _1-6 haloalkoxy group, C _1-6 alkylamino group, C _2-8 dialkylamino group or phenyl group. Compound,
[93] In [92], each R ^u is independently halogen, cyano group, nitro group, C _1-6 alkyl group, C _1-6 haloalkyl group, C _3-8 cycloalkyl group, C _1-6 alkoxy A compound which is a group or a C _1-6 haloalkoxy group,
[94] The compound according to [93], wherein each R ^u is independently a halogen, a C _1-6 alkyl group or a C _1-6 haloalkyl group,
[95] In [94], the compounds wherein R ^u are each independently halogen, a C _1-3 alkyl group or a C _1-3 haloalkyl group,

[96] In [95], the compounds in which R ^u are each independently a fluorine, chlorine, bromine or trifluoromethyl group,
[97] A compound represented by the formula (I) or a compound in which W ¹ is oxygen in [1] to [96],
[98] A compound represented by the formula (I) or a compound in which W ¹ is sulfur in [1] to [96],
[99] A compound represented by formula (I) or a compound obtained by forming a salt in [1] to [98].
Examples of the combinations [1] to [99] shown above include the following.

[A1] In the formula (I),
R ¹ is hydrogen, C _1-6 alkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _1-6 haloalkyl group, C _2-6 haloalkenyl group, C _2-6 haloalkynyl group, C _3-8 cycloalkyl group, C _3-8 halocycloalkyl group, C _4-10 alkyl cycloalkyl group, C _4-10 cycloalkylalkyl group, C _6-14 cycloalkyl cycloalkyl group, C _4-10 halocyclo group An _alkylalkyl group, a C _5-12 alkylcycloalkylalkyl group, a C _2-8 alkoxyalkyl group, a C _4-10 cycloalkoxyalkyl group or a C _3-10 alkoxyalkoxyalkyl group,
R ² is hydrogen, halogen, C _1-6 alkyl group, C _1-6 haloalkyl group, C _3-8 cycloalkyl group or C _2-8 alkoxyalkyl group,
R ³ is hydrogen;
W ² is a C _1-6 alkoxy group,
Each R ^x is independently hydrogen or a C _1-3 alkyl group;
J is heteroaromatic rings benzene ring or a 5- or 6-membered ring, is substituted with up to 3 substituents which the ring is independently selected from R ^u,
Each R ^u is independently halogen, cyano group, hydroxy group, amino group, nitro group, —CHO, —C (═O) OH, —C (═O) NH ₂ , —SO ₂ NH ₂ , SF ₅ , C _1-6 alkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _1-6 haloalkyl group, C _3-8 cycloalkyl group, C _3-8 halocycloalkyl group, C _2-8 alkyl Carbonyl group, C _2-8 haloalkylcarbonyl group, C _2-8 alkoxycarbonyl group, C _2-8 alkylaminocarbonyl group, C _3-10 dialkylaminocarbonyl group, C _1-6 alkoxy group, C _1-6 haloalkoxy group Group, C _2-8 alkylcarbonyloxy group, C _1-6 alkylthio group, C _1-6 haloalkylthio group, C _1-6 alkylsulfonyl group, C _1-6 haloalkylsulfonyl group, C _1-6 alkylaminosulfonyl group C _2-8 dialkylaminosulfonyl group, C _A compound which is a _1-6 alkylamino group, a C _2-8 dialkylamino group, a C _2-8 alkylcarbonylamino group, a C _1-6 alkylsulfonylamino group, a phenyl group, a pyridinyl group or a thienyl group,

[A2] In the formula (I),
R ¹ is hydrogen, a C _1-6 alkyl group, a C _1-6 haloalkyl group or a C _3-8 cycloalkyl group,
R ² is hydrogen, halogen or a C _1-6 alkyl group,
R ³ is hydrogen;
W ² is a C _1-6 alkoxy group,
G is G-3 to G-6, G-9 to G-18, G-22 to G-31, G-33 to G-35, G-39 to G-45, G-48, G-50, Selected from G-53 to G-57, G-59 to G-62 or G-65 to G-68 (wherein the bond on the left of the ring is the bond with the pyridazinone ring of formula (I), Is a bond with J, t represents 0 or 1, and x represents 0, 1 or 2.),
R ^w is independently a halogen, a hydroxy group, a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _3-8 cycloalkyl group, a C _1-6 alkoxy group or a C _1-6 haloalkoxy group. ,
J is a benzene ring, are substituted with up to 3 substituents which the ring is independently selected from R ^u,
Each R ^u is independently halogen, cyano group, nitro group, —CHO, —C (═O) OH, C _1-6 alkyl group, C _1-6 haloalkyl group, C _3-8 cycloalkyl group, C _{3 -8} halocycloalkyl group, C _1-6 alkoxy group, C _1-6 haloalkoxy group, C _1-6 alkylamino group, C _2-8 dialkylamino group or phenyl group,
A compound wherein W ¹ is oxygen,

[A3] In [A2]
R ¹ is hydrogen or a C _1-6 alkyl group,
R ² is hydrogen, chlorine, methyl group or ethyl group,
R ³ is hydrogen;
W ² is a methoxy group or an ethoxy group, G is selected from G-12 to G-15, G-26 to G-29, G-34, G-35 or G-62,
Each R ^w is independently a halogen or a C _1-6 alkyl group;
J is a benzene ring, which is substituted with a substituent which the ring is independently selected from R ^u,
A compound wherein each R ^u is independently a halogen, a C _1-6 alkyl group or a C _1-6 haloalkyl group,

[A4] In the formula (I),
R ¹ is hydrogen, C _1-6 alkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _1-6 haloalkyl group, C _2-6 haloalkenyl group, C _2-6 haloalkynyl group, C _3-8 cycloalkyl group, C _3-8 halocycloalkyl group, C _4-10 alkyl cycloalkyl group, C _4-10 cycloalkylalkyl group, C _6-14 cycloalkyl cycloalkyl group, C _4-10 halocyclo group An _alkylalkyl group, a C _5-12 alkylcycloalkylalkyl group, a C _2-8 alkoxyalkyl group, a C _4-10 cycloalkoxyalkyl group or a C _3-10 alkoxyalkoxyalkyl group,
R ² is hydrogen, halogen, C _1-6 alkyl group, C _1-6 haloalkyl group, C _3-8 cycloalkyl group, C _2-8 alkoxyalkyl group or C _1-4 alkoxy group,
R ³ is hydrogen;
W ² is a C _1-6 alkoxy group,
G is a ring selected from G-1 to G-69,
Each R ^x is independently hydrogen or a C _1-3 alkyl group;
J is heteroaromatic rings benzene ring or a 5- or 6-membered ring, is substituted with up to 3 substituents which the ring is independently selected from R ^u,
Each R ^u is independently halogen, cyano group, hydroxy group, amino group, nitro group, —CHO, —C (═O) OH, —C (═O) NH ₂ , —SO ₂ NH ₂ , SF ₅ , C _1-6 alkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _1-6 haloalkyl group, C _3-8 cycloalkyl group, C _3-8 halocycloalkyl group, C _2-8 alkyl Carbonyl group, C _2-8 haloalkylcarbonyl group, C _2-8 alkoxycarbonyl group, C _2-8 alkylaminocarbonyl group, C _3-10 dialkylaminocarbonyl group, C _1-6 alkoxy group, C _1-6 haloalkoxy group Group, C _2-8 alkylcarbonyloxy group, C _1-6 alkylthio group, C _1-6 haloalkylthio group, C _1-6 alkylsulfonyl group, C _1-6 haloalkylsulfonyl group, C _1-6 alkylaminosulfonyl group C _2-8 dialkylaminosulfonyl group, C _A compound which is a _1-6 alkylamino group, a C _2-8 dialkylamino group, a C _2-8 alkylcarbonylamino group, a C _1-6 alkylsulfonylamino group, a phenyl group, a pyridinyl group or a thienyl group,

[A5] In [A4],
R ¹ is hydrogen, a C _1-6 alkyl group, a C _1-6 haloalkyl group or a C _3-8 cycloalkyl group,
R ² is hydrogen, halogen, C _1-6 alkyl group, C _1-6 haloalkyl group, C _3-8 cycloalkyl group, C _2-8 alkoxyalkyl group or C _1-4 alkoxy group,
G is G-3 to G-6, G-9 to G-18, G-22 to G-31, G-33 to G-35, G-39 to G-45, G-48, G-50, Selected from G-53 to G-57, G-59 to G-62 or G-65 to G-68 (wherein the bond on the left of the ring is the bond with the pyridazinone ring of formula (I), Is a bond with J, t represents 0 or 1, and x represents 0, 1 or 2.),
R ^w is independently a halogen, a hydroxy group, a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _3-8 cycloalkyl group, a C _1-6 alkoxy group or a C _1-6 haloalkoxy group. ,
J is a benzene ring, are substituted with up to 3 substituents which the ring is independently selected from R ^u,
Each R ^u is independently halogen, cyano group, nitro group, —CHO, —C (═O) OH, C _1-6 alkyl group, C _1-6 haloalkyl group, C _3-8 cycloalkyl group, C _{3 -8} halocycloalkyl group, C _1-6 alkoxy group, C _1-6 haloalkoxy group, C _1-6 alkylamino group, C _2-8 dialkylamino group or phenyl group,
A compound wherein W ¹ is oxygen,

[A6] In [A5],
R ¹ is hydrogen or a C _1-6 alkyl group,
R ² is hydrogen, chlorine, methyl group, ethyl group or methoxy group;
W ² is a C _1-6 alkoxy group,
G is selected from G-12 to G-15, G-26 to G-29, G-34, G-35 or G-62;
Each R ^w is independently a halogen or a C _1-6 alkyl group;
J is a benzene ring, which is substituted with a substituent which the ring is independently selected from R ^u,
A compound in which each R ^u is independently a halogen, a C _1-6 alkyl group or a C _1-6 haloalkyl group.

[A7] In [A3] or [A6],
R ¹ is a methyl group,
R ² is hydrogen;
R ³ is hydrogen;
W ² is a C _1-6 alkoxy group,
G is selected from G-12, G-15, G-26, G-28, G-29, G-34, G-35 or G-62;
Each R ^w is independently a methyl group or an ethyl group;
J is a benzene ring, the para-position of the ring is substituted by R ^u,
A compound wherein each R ^u is independently halogen, C _1-3 alkyl group or C _1-3 haloalkyl group,

[A8] In [A7],
G is G-26,
x is 1,
R ^w is bonded to position 5 of G-26,
A compound in which each R ^u is independently a fluorine, chlorine, bromine or trifluoromethyl group.

  The herbicide of this invention and the harmful arthropod control agent of this invention contain this invention compound and an inert support | carrier. Examples of the inert carrier include a solid carrier, a liquid carrier, and a gas carrier. The herbicide of the present invention and the harmful arthropod control agent of the present invention are usually further added with formulation adjuvants such as a surfactant, a sticking agent, a dispersing agent, a stabilizer, and the like. It is formulated into flowables, granules, dry flowables, emulsions, aqueous liquids, oils, smokes, aerosols, microcapsules and the like. The herbicide of the present invention and the harmful arthropod control agent of the present invention usually contain 0.1 to 80% by weight of the compound of the present invention.

Examples of the inert carrier include a solid carrier, a liquid carrier, and a gas carrier.
Examples of the solid carrier include clays (for example, kaolin, diatomaceous earth, synthetic hydrous silicon oxide, fusami clay, bentonite, acidic clay), talc, and other inorganic minerals (for example, sericite, quartz powder, sulfur powder, activated carbon, Examples of the liquid carrier include water, alcohols (for example, methanol, ethanol), ketones (for example, acetone, methyl ethyl ketone), aromatic carbonization, and the like. Hydrogens (eg, benzene, toluene, xylene, ethylbenzene, methylnaphthalene), aliphatic hydrocarbons (eg, n-hexane, cyclohexane, kerosene), esters (eg, ethyl acetate, butyl acetate), nitriles (eg, , Acetonitrile, isobutylnitrile), ethers (eg Dioxane, diisopropyl ether), acid amides (e.g., N, N- dimethylformamide, dimethylacetamide), halogenated hydrocarbons (e.g., dichloroethane, trichlorethylene, and carbon tetrachloride), and the like.

  Examples of the surfactant include alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and polyoxyethylene compounds thereof, polyoxyethylene glycol ethers, polyhydric alcohol esters, sugar alcohol derivatives. Etc.

  Other formulation adjuvants include, for example, fixing agents and dispersants, specifically casein, gelatin, polysaccharides (eg starch, arabic gum, cellulose derivatives, alginic acid), lignin derivatives, bentonite, saccharides, synthetic water-soluble high Molecules (for example, polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids), PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (2-tert-butyl-4) -Mixtures of methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oils, mineral oils, fatty acids or esters thereof.

The weed control method of the present invention includes a step of applying an effective amount of the compound of the present invention to weeds or soil where weeds grow. In the weed control method of the present invention, the herbicide of the present invention is usually used. Examples of the method of applying the herbicide of the present invention include a method of treating the herbicide of the present invention with foliage on weeds, a method of treating the herbicide of the present invention on the soil surface on which weeds grow, and the herbicide of the present invention as a weed. The method of admixing to the soil where the rice grows can be mentioned. In the weed control method of the present invention, the compound of the present invention is usually used in an amount of 1 to 5000 g, preferably 10 to 1000 g, per 10,000 m ^{2 of} area for controlling weeds.

The method for controlling harmful arthropods of the present invention includes a step of applying an effective amount of the compound of the present invention to harmful arthropods or the habitat of harmful arthropods. In the method for controlling harmful arthropods of the present invention, a preparation containing the compound of the present invention is usually used.
When the compound of the present invention is used for controlling agricultural and forestry pests, the application amount of the compound of the present invention is usually 1 to 10000 g / ha, preferably 10 to 1000 g / ha. Examples of the method for controlling harmful arthropods of the present invention include a method in which a preparation containing the compound of the present invention is sprayed on plants to be protected from harmful arthropods. By treating the preparation containing the compound of the present invention with soil, harmful arthropod organisms that live in the soil can be controlled.
When the compound of the present invention is used for controlling a pest control insect, the application amount of the compound of the present invention is usually 0.001 to 10 mg / m ³ when applied to a space, and 0.001 to 100 mg / m ³ when applied to a plane. m ² .

The compound of the present invention can be used in farmland where the “plants” listed below are cultivated.
“Plants”: crops: corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, buckwheat, sugar beet, rapeseed, sunflower, sugarcane, tobacco, etc.
Vegetables: Solanum vegetables (eggplants, tomatoes, peppers, peppers, potatoes, etc.), Cucurbitaceae vegetables (cucumbers, pumpkins, zucchini, watermelons, melons, etc.), Brassicaceae vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage) , Mustard, broccoli, cauliflower, etc.), asteraceae vegetables (burdock, shungiku, artichoke, lettuce, etc.), lily family vegetables (eg, leek, onion, garlic, asparagus, etc.), celery family vegetables (carrot, parsley, celery, American redfish) Etc.), red crustacean vegetables (spinach, chard, etc.), persimmon vegetables (perilla, mint, basil, etc.), strawberry, sweet potato, yam, taro, etc.
Fruit trees: berries (apples, pears, Japanese pears, quince, quince, etc.), nuclear fruits (peaches, plums, nectarines, ume, sweet cherry, apricot, prunes, etc.) ), Nuts (chestnut, walnut, hazel, almond, pistachio, cashew nut, macadamia nut, etc.), berries (blueberry, cranberry, blackberry, raspberry, etc.), grape, oyster, olive, loquat, banana, coffee, Date palm, coconut palm, oil palm etc.
Trees other than fruit trees: tea, mulberry, flowering trees (Satsuki, camellia, hydrangea, sasanqua, shikimi, sakura, yurinoki, crape myrtle, snapdragon, etc.), roadside trees (ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple, oak) , Poplar, redwood, fu, sycamore, zelkova, blackfish, Japanese amberjack, moths, pine, pine, spruce, yew, elm, Japanese cypress, etc.), coral jug, dogwood, cedar, cypress, croton, masaki, kanamochi, etc.
Other: Flowers (Rose, Carnation, Chrysanthemum, Eustoma, Gypsophila, Gerbera, Marigold, Salvia, Petunia, Verbena, Tulip, Aster, Gentian, Lily, Pansy, Cyclamen, Orchid, Lily of the valley, Lavender, Stock, Habutton, Primula, Poinsettia, gladiolus, cattleya, daisy, symbidium, begonia, etc.), biofuel plants (Jatropha, safflower, Amanas, switchgrass, miscanthus, kusayoshi, dangiku, kenaf, cassava, willow, etc.), houseplants, etc.

The “plant” includes 4-hydroxyphenylpyruvate dioxygenase (hereinafter abbreviated as HPPD) inhibitors such as isoxaflutole, and acetolactate synthase (hereinafter abbreviated as ALS) such as imazetapyr and thifensulfuron methyl. Inhibitors, 5-enolpyruvylshikimate-3-phosphate synthase (hereinafter abbreviated as EPSPS) inhibitors such as glyphosate, glutamine synthetase inhibitors such as glufosinate, acetyl CoA carboxylase inhibitors such as cetoxydim, flumioxazine, etc. Also included are plants that have been given resistance to auxin herbicides such as protoporphyrinogen oxidase inhibitors, dicamba and 2,4-D, herbicides such as bromoxynil by classical breeding methods or genetic recombination techniques .
Examples of “plants” tolerated by classical breeding methods include rapeseed, wheat, sunflower, rice and corn that are resistant to imidazolinone-based ALS-inhibiting herbicides such as imazetapy. Already sold under the trade name> Similarly, there are STS <(R)> soybeans that are resistant to sulfonylurea ALS-inhibiting herbicides such as thifensulfuron-methyl by classical breeding methods. Similarly, SR corn and the like are examples of plants to which tolerance has been imparted to acetyl CoA carboxylase inhibitors such as trion oxime and aryloxyphenoxypropionic acid herbicides by classical breeding methods.

  Examples of “plants” that have been rendered resistant by genetic recombination techniques include glyphosate-resistant maize, soybean, cotton, rapeseed, and sugar beet varieties having EPSPS genes that are resistant to EPSPS inhibitors. RoundupReady <registered Have already been sold under trade names such as Trademark>, Agrisure <registered trademark> GT, Gly-Tol. Similarly, there are corn, soybean, cotton, and rapeseed varieties that are resistant to glufosinate by gene recombination technology, and are already sold under trade names such as LibertyLink (registered trademark). Similarly, bromoxynyl-resistant cotton by gene recombination technology is already sold under the trade name BXN. Similarly, there are corn and soybean varieties that are resistant to both glyphosate and ALS inhibitors, and the trade name of Optimum <(R)> GAT <(R)> has been published.

  Further, mutant acetyl CoA carboxylase resistant to acetyl CoA carboxylase inhibitors has been reported in Weed Science, 53, 728-746 (2005), etc., and such mutant acetyl CoA carboxylase gene can be transferred to plants by gene recombination technology. A plant resistant to an acetyl-CoA carboxylase inhibitor can be produced by introducing a mutation associated with introduction or resistance imparting into a crop acetyl-CoA carboxylase. Further, a base substitution mutation-introduced nucleic acid represented by chimera plastic technology (Gura T. 1999. Repairing the Genome's Spelling Mistakes. Science 285: 316-318.) Is introduced into plant cells, and then plant acetyl-CoA carboxylase is introduced. By introducing a site-specific amino acid substitution mutation into a gene or ALS gene, a plant resistant to an acetyl CoA carboxylase inhibitor or an ALS inhibitor can be produced.

In addition, a gene encoding a dicamba monooxygenase containing dicamba monooxygenase isolated from Pseudomonas maltophilia can be introduced to produce a crop such as soybean resistant to dicamba. (Behrens et al. 2007 Dicamba Resistance: Enlarging and Preserving Biotechnology-Based Weed Management Strategies. Science 316: 1185-1188).
Introducing a gene encoding aryloxyalkanoate dioxygenase, phenoxy herbicides such as 2,4-D, MCPA, dicloprop, mecoprop, pyridineoxyacetic acid systems such as fluroxypyr, triclopyr; Of aryloxyphenoxypropionic acid herbicides such as quizalofop-P-ethyl, haloxyhop-P-methyl, fluazihop-P-butyl, dicloholop, phenoxaprop-P-ethyl, metamihop, cyhalohop-butyl, clodinafop-propargyl, It is possible to produce crops that are resistant to both herbicide lines (WO2005 / 107437, WO2007 / 053482, WO2008 / 141154), D It is called HT crop.

  Furthermore, a gene encoding HPPD showing resistance to an HPPD inhibitor can be introduced to produce a plant resistant to the HPPD inhibitor (US2004 / 0058427). Even if HPPD is inhibited by an HPPD inhibitor, a gene that can synthesize homogentisic acid, which is a product of HPPD, by another metabolic pathway is introduced, and as a result, a plant that is resistant to the HPPD inhibitor is created. (WO02 / 036787). A gene that overexpresses HPPD is introduced, and even in the presence of an HPPD inhibitor, HPPD is produced in an amount that does not affect the growth of the plant. As a result, a plant that is resistant to the HPPD inhibitor is produced. Can be produced (WO 96/38567). In addition to the introduction of a gene that overexpresses HPPD described above, a gene encoding prephenate dehydrogenase was introduced to increase the amount of p-hydroxyphenylpyruvic acid that is a substrate of HPPD, thereby inhibiting HPPD (Rippert P et.al. 2004 Engineering plant shikimate pathway for production of tocotriol and improvising herb.

  Examples of "plants" that have been given resistance by classical breeding methods include plants that are resistant to nematodes and aphids. RAG1 and the like are known as genes that bring about traits resistant to aphids.

The “plant” includes a plant that can synthesize, for example, a selective toxin known in the genus Bacillus, using a gene recombination technique.
Examples of insecticidal toxins expressed in such genetically modified plants include insecticidal proteins derived from Bacillus cereus and Bacillus popillie; Cry1Ab derived from Bacillus thuringiensis , Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, etc., insecticidal proteins such as VIP1, VIP2, VIP3 or VIP3A; nematode-derived insecticidal proteins; Toxins produced by animals such as insect-specific neurotoxins; filamentous fungal toxins; plant lectins; agglutinins; trypsin inhibitors, serine protease inhibitors, Protease inhibitors such as tachin, cystatin, papain inhibitor; ribosome inactivating protein (RIP) such as lysine, corn-RIP, abrin, ruffin, saporin, bryodin; 3-hydroxysteroid oxidase, ecdysteroid-UDP-glucosyl Steroid metabolic enzymes such as transferase and cholesterol oxidase; ecdysone inhibitor; HMG-CoA reductase; ion channel inhibitors such as sodium channel inhibitor and calcium channel inhibitor; juvenile hormone esterase; diuretic hormone receptor; stilbene synthase; Synthase; chitinase; glucanase and the like.
Moreover, as toxins expressed in such genetically modified plants, Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C and other δ-endotoxin proteins, VIP1, VIP2, VIP3 or VIP3A and other insecticidal proteins Also included are hybrid toxins, partially defective toxins, and modified toxins. Hybrid toxins are produced by new combinations of different domains of these proteins using recombinant techniques. As a toxin lacking a part, Cry1Ab lacking a part of the amino acid sequence is known. In the modified toxin, one or more amino acids of the natural toxin are substituted.
Examples of these toxins and recombinant plants capable of synthesizing these toxins are disclosed in, for example, EP-A-0374753, WO93 / 07278, WO95 / 34656, EP-A-0427529, EP-A-451878, WO03 / 052073, etc. Are listed.
Toxins contained in these recombinant plants particularly confer resistance to Coleoptera, Diptera pests, and Lepidoptera pests.

  In addition, genetically modified plants that contain one or more insecticidal pest resistance genes and express one or more toxins are already known, and some are commercially available. Examples of these genetically modified plants include YieldGuard (registered trademark) (a corn variety that expresses Cry1Ab toxin), YieldGuard Rootworm (registered trademark) (a corn variety that expresses Cry3Bb1 toxin), YieldGuard Plus (registered trademark) (a corn variety expressing Cry1Ab and Cry3Bb1 toxin), Herculex I (registered trademark) (phosphino to confer resistance to Cry1Fa2 toxin and glufosinate Corn varieties expressing tricine N-acetyltransferase (PAT)), NuCOTN33B <(registered trademark)> (cotton varieties expressing Cry1Ac toxin), Volgaard I (Bollg) rd I) <registered trademark> (cotton variety expressing Cry1Ac toxin), Volgard II (registered trademark) (cotton variety expressing Cry1Ac and Cry2Ab toxin), VIPCOT <registered trademark> (expressing VIP toxin) Cotton Leaf), New Leaf <registered trademark> (potato variety that expresses Cry3A toxin), NatureGuard <registered trademark>, Agrisure GT Advantage (GA21 glyphosate tolerance) Traits), Aggresure CB Advantage (Agriure <(R)> CB Advantage) (Bt11 corn borer (CB) trait), Protector <(R)>, and the like.

The “plant” includes those imparted with an ability to produce an anti-pathogenic substance having a selective action using a gene recombination technique.
Examples of anti-pathogenic substances include PR proteins (described in PRPs, EP-A-0392225); sodium channel inhibitors, calcium channel inhibitors (virus-produced KP1, KP4, KP6 toxins, etc.) Stilbene synthase; bibenzyl synthase; chitinase; glucanase; peptide antibiotics, antibiotics having heterocycles, substances produced by microorganisms such as protein factors involved in plant disease resistance, etc. Can be mentioned. Such anti-pathogenic substances and genetically modified plants that produce them are described in EP-A-0392225, WO95 / 33818, EP-A-0353191, and the like.

  The above “plant” includes plants imparted with useful traits such as oil component modification and amino acid content enhancing traits using genetic recombination techniques. Examples include VISTIVE <(R)> (low linolenic soybeans with reduced linolenic content) or high-lysine (high-oil) corn (corn with increased lysine or oil content).

  In addition, the above-mentioned classic herbicide traits or herbicide resistance genes, insecticidal pest resistance genes, anti-pathogenic substance production genes, oil traits modification, amino acid content enhancement traits, etc. Combined stack varieties are also included.

  When the compound of the present invention is used for a herbicide-tolerant plant, the herbicide to which the plant is tolerated (for example, glyphosate or a salt thereof, glufosinate or a salt thereof, dicamba or a salt thereof, imazetapyr or a salt thereof, It is possible to control weeds comprehensively by systemic treatment or / and mixed treatment of isoxaflutol etc.) and the compound of the present invention.

  The compound of the present invention can be mixed or used in combination with other insecticides, acaricides, nematicides, fungicides, herbicides, plant growth regulators, synergists and / or safeners.

Examples of the active ingredient of such an insecticide include the following.
(1) Organophosphorus compound Acephate, Butathiofos, Chlorethoxyphos, Chlorfenvinfos, Chlorpyrifos, Chlorpyrifos-Methyl (Chlorpyrifos) , Diazinon, diclofenthion (ECP), dichlorvos (DDVP), dimethoate, dimethylvinphos, disulfoton, EPth, ethione Lofos, etrimfos, fenthion (MPP), phennitrothion (MEP), fothiazate, formothion, thoxathion, isoxathion, isoxathion, isoxathion (Mesulfofos), methidathion (DMTP), monocrotophos, monored (BRP), oxydeprofos (ESP), parathion, phosalone, phosmetone hosmet: PMP, pirimiphos-methyl, pyridafenthion, quinalphos, phentoate: PAP, profenofos, propiophos, propiophos, propofos (Salithion), sulprofos, tebupyrimfos, temefos, tetrachlorvinphos, terbufos, thiomethon, trichlorfon (trichon) lonpho: DEP), bamidithione, formate, kazusafos.

(2) Carbamate compounds alaniccarb, bendiocarb, benfurcarb, BPMC, carbaryl, carbofuran, carbothofen, lofocarb, lofocarb , Fenobucarb, phenothiocarb, phenoxycarb, furatiocarb, isoprocarb (MIPC), methocarb (metolcarb) hiocarb), oxamyl (oxamyl), pirimicarb (pirimicarb), propoxur (propoxur: PHC), XMC, thiodicarb (thiodicarb), xylylcarb (xylylcarb), aldicarb (aldicarb).

(3) Pyrethroid compounds Acrinathrin, allethrin, beta-cyfluthrin, bifenthrin, cycloprotorin, cyfluthrin, cyfluthrin, cyfluthrin, cyfluthrin, cyfluthrin ), Empentrin, deltamethrin, esfenvalerate, ethofenprox, fenpropathrin, fenvalerate, flucitrate (fl) ucythrinate, flufenprox, flumethrin, fluvalinate, halfenprox, imiprothrin, permethrin, praretrin, rmethrin. resmethrin), sigma-cypermethrin, silafluofen, tefluthrin, tralomethrin, transfluthrin, tetramethrin. hrin), phenothrin, cyphenothrin, alpha-cypermethrin, zeta-permethrin, lambda cihalothrin (lambda-halothrin) ), Furamethrin, tau-fluvalinate, methfluthrin, profluthrin, dimethylfluthrin, 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl 2 , 2-Dimethyl-3- (2-cyano-1-propyl) Propenyl) cyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl 2,2,3,3-tetramethyl-cyclopropanecarboxylate, protrifenbute (Protrifenbute).

(4) Nereistoxin compound Cartap, bensultap, thiocyclam, monosultap, bisultap.

(5) Neonicotinoid compounds Imidacloprid, nitenpyram, acetamiprid, thiamethoxam, thiacloprid, dinotefuran (dinoteurin)

(6) Benzoylurea compounds Chlorfluazuron, bistrifluron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron (flufluxuron) hexafluuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron.

(7) Phenylpyrazole compound Acetoprole, etiprole, fipronil, vaniliprole, pyriprole, pyrafluprole.

(8) Bt toxin Live spores and produced crystal toxins derived from Bacillus thuringiensis, and mixtures thereof.

(9) Hydrazine compounds Chromafenozide, halofenozide, methoxyphenozide, tebufenozide.

(10) Organochlorine compound Aldrin, dieldrin, chlordane, DDT, dienochlor, endosulfan, methoxychlor.

(11) Other insecticidal active ingredients machine oil, nicotine sulfate (nicotine-sulfate); avermectin (avermectin-B), bromopropyrate, buprofezin, chlorfenacyl (chlorophylline) ), DCIP (dichroroisopropyl ether), DD (1,3-Dichloropropene), emamectin benzoate, fenazaquin, flupirazofo re, meprene , Indoxacarb, methoxadiazone, milbemycin-A, pymetrozine, pyridalyl, pyriprosulfur, inspiramide, spinomidol tolfenpyrad, triazamate, fulbenamide, flumectin, lepimectin, aluminum phosphide, arsenous oxide, benclothiaz (benclothiaz) Ium cyanamide, calcium polysulfide, DSP, flonicamid, flurimfen, formatenate, hydrogen phosphide, metam ammonium, metam ammonium, metam ammonium, metam ammonium Sodium (metham-sodium), methyl bromide, potassium oleate, spiromesifene, sulfur, metaflumizone, spirotetraflutir one), spinetoram (spinetoram), chlorantraniliprole (chlorantraniliprole), Toraropiriru (tralopyril), diafenthiuron (diafenthiuron),

（式中、Ｘ^a1はメチル基、塩素、臭素又はフッ素を表し、Ｘ^a2はフッ素、塩素、臭素、Ｃ₁−Ｃ₄ハロアルキル基又はＣ₁−Ｃ₄ハロアルコキシ基を表し、Ｘ^a3はフッ素、塩素又は臭素を表し、Ｘ^a4は置換されていてもよいＣ₁−Ｃ₄アルキル、置換されていてもよいＣ₃−Ｃ₄アルケニル、置換されていてもよいＣ₃−Ｃ₄アルキニル、置換されていてもよいＣ₃−Ｃ₅シクロアルキルアルキル又は水素を表し、Ｘ^a5は水素又はメチル基を表し、Ｘ^a6は水素、フッ素又は塩素を表し、Ｘ^a7は水素、フッ素又は塩素を表す。）
で示される化合物、 Formula (A)

( ^Wherein X ^a1 represents a methyl group, chlorine, bromine or fluorine, X ^a2 represents a fluorine, chlorine, bromine, C ₁ -C ₄ haloalkyl group or C ₁ -C ₄ haloalkoxy group, and X ^a3 represents fluorine. Represents a chlorine or bromine, and X ^a4 is an ^optionally substituted C ₁ -C ₄ alkyl, an optionally substituted C ₃ -C ₄ alkenyl, an optionally substituted C ₃ -C ₄ alkynyl, a substituted C ₃ -C ₅ cycloalkylalkyl or hydrogen which may be ^substituted , X ^a5 represents hydrogen or a methyl group, X ^a6 represents hydrogen, fluorine or chlorine, and X ^a7 represents hydrogen, fluorine or chlorine. )
A compound represented by

（式中、Ｘ^b1はＸ^b2−ＮＨ−Ｃ（＝Ｏ）基、Ｘ^b2−Ｃ（＝Ｏ）−ＮＨ−ＣＨ₂基、Ｘ^b3−Ｓ（Ｏ）基、置換されていてもよいピロール−１−イル基、置換されていてもよいイミダゾール−１−イル基、置換されていてもよいピラゾール−１−イル基又は置換されていてもよい１，２，４−トリアゾール−１−イル基を表し、Ｘ^b2は２，２，２−トリフルオロエチル基等の置換されていてもよいＣ₁−Ｃ₄ハロアルキル基又はシクロプロピル基等の置換されていてもよいＣ₃−Ｃ₆シクロアルキル基を表し、Ｘ^b3はメチル等の置換されていてもよいＣ₁−Ｃ₄アルキル基を表し、Ｘ^b4は水素、塩素、シアノ基又はメチル基を表す。）で示される化合物、 Formula (B)

(In the formula, X ^b1 is X ^b2 —NH—C (═O) group, X ^b2 —C (═O) —NH—CH ₂ group, X ^b3 —S (O) group, optionally substituted pyrrole) -1-yl group, optionally substituted imidazol-1-yl group, optionally substituted pyrazol-1-yl group, or optionally substituted 1,2,4-triazol-1-yl group X ^b2 represents an optionally substituted C ₁ -C ₄ haloalkyl group such as a 2,2,2-trifluoroethyl group or an optionally substituted C ₃ -C ₆ cycloalkyl such as a cyclopropyl group. X ^b3 represents an ^optionally substituted C ₁ -C ₄ alkyl group such as methyl, and X ^b4 represents hydrogen, chlorine, a cyano group, or a methyl group.

（式中、Ｘ^c1は３，３，３−トリフルオロプロピル基等の置換されていてもよいＣ₁−Ｃ₄アルキル基、２，２，２−トリクロロエトキシ基等の置換されていてもよいＣ₁−Ｃ₄アルコキシ基、４−シアノフェニル基等の置換されていてもよいフェニル基又は２−クロロ−３−ピリジル基等の置換されていてもよいピリジル基を表し、Ｘ^c2はメチル基又はトリフルオロメチルチオ基を表し、Ｘ^c3はメチル基又はハロゲンを表す。）
で示される化合物。 Formula (C)

(In the formula, X ^c1 may be a substituted C ₁ -C ₄ alkyl group such as a 3,3,3-trifluoropropyl group or the like, a 2,2,2-trichloroethoxy group or the like. A C ₁ -C ₄ alkoxy group, a phenyl group which may be substituted such as 4-cyanophenyl group or a pyridyl group which may be substituted such as 2-chloro-3-pyridyl group, and X ^c2 is a methyl group Alternatively, it represents a trifluoromethylthio group, and X ^c3 represents a methyl group or a halogen.)
A compound represented by

Examples of the active ingredient of such an acaricide include the following.
Acequinocyl, amitraz, benzoximate, bifenazate, bromopropyrate, chinomethionate, BS chlorbenzylate clofenetine, cyflumethofen, kelsen (dicofol), etoxazole, fenbutatin oxide, fenothiocarb, fenpyroximate , Fluacrylpyrim, halfenprox, hexythiazodi, propargite tetrapene, fendipenti, pyridene, pyridene ), Spirodiclofen, spiromesifen, spirotetramat, amidoflumet, and cienopyrafen.

Examples of the active ingredient of such a nematicide include the following.
DCIP, fothiazate, levamisole hydrochloride, methylisothiocyanate, morantel tartrate, and imicyafos.

Examples of the active ingredient of such a bactericide include the following.
(1) Polyhaloalkylthio compound captan, folpet, etc.
(2) Organophosphorus compounds IBP, EDDP, torquelofos-methyl and the like.
(3) Benzimidazole compound,
Benomyl, carbendazim, thiophanate-methyl, thiabendazole, etc.
(4) Carboxamide compounds Carboxin, mepronil, flutolanil, thifluzamide, furametopyr, boscalid, pentiopyrad, etc.
(5) Dicarboximide compound Procymidone, iprodione, vinclozolin, etc.
(6) Acylalanine compound metalaxyl, etc.
(7) Azole compounds Triadimefon, triadimenol, propiconazole, tebuconazole, cyproconazole, epoxiconol, and epoxiconazole ), Ipconazole, triflumizole, prochloraz, penconazole, flusilazole, dinicoazole, bromconazole, bromconazole, bromconazole, bromconazole Difenoconazole, metconazole, tetraconazole, microbutanil, fenbuconazole, hexaconazole, fluconazole, fluconazole, fluconazole, fluconazole. tritonicazole, bittertanol, imazalil, flutriafol, etc.
(8) Morpholine compound Dodemorph, tridemorph, fenpropimorph, and the like.
(9) Strobilurin compounds azoxystrobin, cresoxime-methyl, methminostrobin, trifloxystrobin, picoxystrobin (picoxystrobin), cross Fluoxastrobin, dimoxystrobin, etc.
(10) Antibiotics Validamycin A, blastcidin S, kasugamycin, polyoxin and the like.
(11) Dithiocarbamate compounds Mancozeb, maneb, thiuram and the like.
(12) Other Bactericidal Active Ingredients Fthalide, Probenazole, Isoprothiolane, Tricyclazole, Pyroquilon, Ferimzone, olprozone carpropamid, diclocymet, phenoxanil, thiazinyl, diclomezine, teclophthalam, pencycuron, oxolinic acid, oxolinic acid, x Rifoline, fenpropidin, spiroxamine, fluazinam, iminooctadine, fenpiclonil, fludioxonimide, fludioxonimide, fludioxonimide , Silthiofam, proquinazide, cyflufenamide, basic copper calcium sulfate, dichlorofluanid, cyprodinil (cypropyridinyl) ethanil, mepanipyrim, dietofencarb, pyribencarb, famoxadone, fenamidone, fenamidone, fenamidone, fenamidone Valicarb (benthiavalicarb), cyazofamid (cyazofamid), mandipropamide (mandipropamid), metraphenone (metrafenone), fluopiram (fluopiram), bixafen (bixafen) and the like.

Examples of the active ingredients of such herbicides include the following.
(1) Phenoxy fatty acid compound 2,4-PA, MCP, MCPB, phenothiol, mecoprop, fluroxypyr, triclopyr, clomeprop, naproanilide (naroanilide)
(2) Benzoic acid compound 2,3,6-TBA, dicamba, clopyralid, picloram, aminopyralide, quinclorac, quinmerac, etc.
(3) Urea compounds diuron, linuron, chlortoluron, isoproturon, fluometuron, isouron, tebuthiuron, methizuron, metabenthuron (Cumyluron), daimuron, methyl-daimulon, etc.,
(4) Triazine compounds atrazine, ametrine, cyanazine, simazine, propazine, simetrin, dimetamethrin, dimethylmethrin Triaziflam, indaziflam, etc.].
(5) Bipyridinium compounds [paraquat, diquat, etc.
(6) Hydroxybenzonitrile compound Bromoxynil, ioxynil, etc.
(7) Dinitroaniline compound Pendimethalin, prodiamine, trifluralin, etc.
(8) Organophosphorus compound Amiprofos-methyl, butamifos, bensulide, piperophos, anilofos, glyphosate, glufosinate, glufosinate glufosinate-P), bialaphos, etc.
(9) Carbamate compounds di-allate, tri-allate, EPTC, butyrate, benthocarb, esprocarb, molinate, dimepiperate, spep ), Chlorpropham, phenmedifam, phenisopham, pyributicalcarb, ashram, etc.,
(10) Acid amide compound propanil, propyzamide, bromobutide, etobenzanide and the like].
(11) Chloroacetanilide compounds [acetochlor, alachlor, butachlor, dimethenamid, propachlor, metazachlor, retrachor, and metholachlor ), Tenylchlor, petoxamide, etc.
(12) Diphenyl ether compounds aciflufen-sodium, bifenox, oxyfluorfen, lactofen, fomesafen, clomethoxynyl, clomethoxyxyfen
(13) Cyclic imide compounds Oxadiazone, cinidone-ethyl, carfentrazone-ethyl, sulfentrazone, flumicrolac-pentyl, flumioxazin (flumioxazine) flumioxazin, pyraflufen-ethyl, oxadiargyl, pentoxazone, fluthiacet-methyl, carbene, benzfenezyl e), saflufenacil (saflufenacil), etc.,
(14) Pyrazole compound Benzofenap, pyrazolate, pyrazoxifene, topramzone, pyrasulfotole, etc.
(15) Triketone compounds isoxaflutole, benzobicyclon, sulcotrione, mesotrione, tembotrione, tefurylcyclone, tefuryltricone
(16) Aryloxyphenoxypropionic acid compound clodinahop-propargyl, cyhalofop-butyl, diclohop-methyl, phenoxaprop-ethyl, fenoxaprop-ethyl Hopbutyl, haloxyhop-methyl, quizalofop-ethyl, metamihop, etc.
(17) Trione oxime compounds alloxydim-sodium, cetoxydim, butoxydim, crestodim, cloxydim, cycloxidim, tepraxidim, tepraxidim ), Propoxydim, etc.
(18) Sulfonylurea compounds Chlorsulfuron, sulfomethuron-methyl, metsulfuron-methyl, chlorimuron-ethyl, tribenuron-methyl (tribenuron) methyl, trisulfuron, bensulfuron-methyl, thifensulfuron-methyl, pyrazosulfuron-ethyl, prisulfuron methyl. (Nicosulfu on), amidosulfuron, cinosulfuron, imazosulfuron, rimsulfuron, halosulfuron-methyl, prosulfuron, prosulfuron. , Triflusulfuron-methyl, flazasulfuron, cyclosulfamuron, flupirsulfuron, sulfosulfurfuron, asulfurfuron sulfuron, ethoxysulfuron, oxasulfuron, iodosulfuron-methyl-sodium, foramsulfuron, mesosulfuron, messulfuron-methyl (Trifloxysulfuron), tritosulfuron, orthosulfamuron, flucetosulfuron, propyrisulfuron, metazosulfuron, metazosulfuron, etc.
(19) imidazolinone compounds imazametabenz-methyl, imazametapyr (imazamox), imazapyr (imazapir), imazaquin (imizamuir)
(20) Sulfonamide compounds Flumeslam, metosulam, dicloslam, floraslam, chloranthram-methyl, penoxsulam, pixoxram
(21) Pyrimidinyloxybenzoic acid compound pyrithiobac-sodium, bispyribac-sodium, pyriminobac-methyl, pyribenzoxim, pyrifaltyl p Fans (pyrimisulfan), etc.
(22) Other herbicidal active ingredients: Bentazone, bromacil, terbacil, chlorthiamid, isoxaben, dinoseb, amitrol, inmethyline, cinmeline Tridiphane, dalapon, diflufenzopyr-sodium, dithiopyr, thiazopyr, sodium flucarbazone, flucarbazone , Mefenacet, flufenacet, fentrazamide, caffentrol, indanophan, oxaziclomefone, benfrate, benfrate Norflurazon, flurtamone, diflufenican, picolinafene, beflubutamid, clomazone, amicarbazone z one), pinoxaden, pyraclonil, pyroxasulphone, thiencarbazone-methyl, aminocyclopyrazole (thibenzoen) Phenoxasulfone, etc.

Examples of active ingredients of such plant growth regulators include the following.
Hymexazole, paclobutrazol, uniconazole-P, inabenfide, prohexadiene-calcium, abiglycinyl, aviglycinamide Abscisic acid, indolebutyric acid, ethiclozate, etephon, cloxyphonac, chlormequat, dichlorprop (Gibberellins), prohydrojasmon, benzylaminopurine, forchlorfenuron, maleic hydrazide, maleic hydride, calcium peroxide chloride), and 4-CPA (4-chlorophenetic acid).

Examples of the active ingredient of such a synergist include the following.
Piperonyl butoxide, sesamex, sulfoxide, N- (2-ethylhexyl) -8,9,10-trinorborn-5-ene-2,3-dicarboximide (MGK 264) N-decrimimidazole, WARF-antiresistant, TBPT, TPP, IBP, PSCP, methyl iodide (CH ₃ I), t-phenylbutenone Diethyl maleate, DMC, FDMC, ETP, and ETN.

Thus, examples of the safening agent include the following.
Furilazole, dichlormid, benoxacor, aldidochlor, isoxadifen-ethyl, fenchlorazole-ethyl, mepyl-ethyl , Cloquintocet-mexyl, fenchlorim, cyprosulfamide, cyometrinil, oxabetrinil, fluxofenol (fluxofolol) Dichloro-2-methyl-1,3-dioxolane (2-dichloromethyl-2-methyl-1,3-dioxolane), and 1,8-naphthalic anhydride (1,8-naphthalic anhydride).

Examples of the control target of the herbicide of the present invention include the following.
Bark beetle (Digitalia ciliaris), Bark beetle (Eleusine i)
ndica), Enocorogusa (Setaria viridis), Aquinoenokorogusa (Setaria Faberi), Echinocerospora (Setaria glauca)
), Echinochloa crus-galli, Greater millet (Pa
nicum dichotomiflorum), Texas Panicum (Panicum)
texanum), Brachiaria platyphylla
), Alexander grass (Brachiaria plantainea), Suriname grass (Brachiaria decumbens), Seban sorghum (Sorg
hum halense), shutter cane (Andropogon sorgh)
um), cynodon dactylon, oat (Avena)
fatua, Lolium multiflorum, blackgrass (Alopecurus myosuroides), Umanochahi (Bromos)
tectorum), retinochahiki (Bromus sterilis), Himekanariku Sayoshi (Phalaris minor), Atlantica sp (Apera sp)
ica-venti), sparrow anemone (Poa annua), shibamugi (Agro)
pylon repens), Cyperus iria, Cyperus rotundus, Cyperus esculen
tus, purslane (Portulaca oleracea), Aogateto (Am)
aranthus retroflexus, Amaranthus Amaranth
us hybridus), Amaranthus palm
eri), water hemp (Amaranthus rudis), ichibi (Abut)
ilon theophrasti), American deer (Sida spinosa)
), Buckwheat (Fallopia convolvulus), sanaetade (Poly)
gonum scabrum), American Sanadeta (Persicaria penn)
sylvanica), Harutade (Persicaria vulgaris), Nagabegishigishi (Rumex crispus), Ezonogishigishi (Rumex obtusi)
folius, Japanese knotweed (Fallopia japonica), Shiroza (Chen)
Opodium album, Kochia scoparaia, Polygonum longisetum, Solenum nun
igrum), white dragonfly (Dataura strononium),
Marsh morning glory (Ipomoea purpurea), American morning glory (Ipomo)
ea hederacea), Malva America morning glory (Ipomoea hedera)
cea var. integriuscula), Ipomoea l
acunasa), Convolvulus arvensis,
Lamium purpureum, Photonosa (Lamium)
amplexicule, onamomi (Xanthium pensylvanicu)
m), wild sunflower (Helianthus annuus), dog chamomile (Matr)
icaria perforata or inodora), chamomile (Matric)
aria chamomilla), corn marigold (Chrysanthemu)
m segetum), Oroshagiku (Matricaria matricario)
des), ragweed (Ambrosia artemisia folia), giant grass (Ambrosia trifida), wormwood calyx (Erigeron ca)
nadensis), mugwort (Artemisia princeps), Solidago altissima, Coneriza b
onariensis), American tunoxanem (Sesbania exalta)
), Cassia obtusifolia, Florida Begerweed (
Desmodium tortousum), white clover (Trifolium re)
pens), Kudzu (Pueraria lobata), Viburnum (Vicia)
angustifolia), commune (Commelina communis),
Camelina benghalensis, Gaemula (Ga
lium aline, Jacobe (Stellaria media), Wild Radish (Raphanus raphanistrum), Noragarashi (Sina)
pis arvensis), Nazuna (Capsella bursa-pastori)
s), Veronica persica, Fragrant (Ver.)
onica hedefolia, field pansy (Viola arven)
sis), wild pansies (Viola tricolor), daisies (Papav)
er rhoeas), forget-me-nots (Myosotis scorpioides),
Japanese creeper (Asclepias syriaca), Euphorb (Euphorb)
ia helioscopia), Chrysanthemum nutan
s), American Furo (Gerenium carolinianum), Dutch Furo (Erodium cicutarium), Horsetail (Equisetum curve)
nse), sea lion (Leersia japonica), Tainubie (Echino)
chloa oryzicola), Echinochloa cru
s-galli var. formationsensis, Azegaya (Leptochlo)
a chinensis), Cyperus differenceris, Hidedelico (Fimbristis miriacea), Matsubai (Eleochar)
is acicularis), Sirpus juncoides
, Sirepus wallichi, Cyper (Cyper)
us serotinus), Krogoi (Eleocharis kuroguwai)
), Bobchoschoenus koshevnikovii, Shizui (Schoenoplectus nipponicus), Konogi (Monocho)
ria vaginalis), Azena (Lindernia procumbens)
, Abnome (Dopatrium junceum), Kikashigusa (Rotala in
dica), himemisohagi (Ammania multiflora), mizohakobe (
Elatine tridra), Crested radish (Ludwigia epilob)
ioides), Urikawa (Sagittaria pygmaea), Heramodaka (
Alisma canaliculatum, Omodaka (Sagittaria tr)
ifolia, Potamogeton distinctus, Seri (Oenanthe javanica), Mizuhakobe (Callirichiche pa)
lutris), azepan pepper (Lindernia milantha), American Azena (Lindernia dubia), Takasaburo (Eclipse)
ostrata, mussel (Murdannia keisak), Pasalum distichum, ezonosayanukagusa (Leersia)
oryzoids). Naganetsurunogateto (Alternanthera)
philoxeroides), frogs bit (Limnobium spong)
ia), Water Fern (genus Salvinia), Duckweed (Pistia)
strateotes), water pennywort (genus Hydrocotyle), filamentous algae (genus Pithophora, cladophora), cune tail (Cera)
tophyllum demersum), duckweed (genus Lemna), scallop (C
aboba caroliniana), chromo (Hydrilla vertici)
llata), Southern naad (Najas guadalupensis), Poundweed crispus, Potamogeton ill
inoensis, Potamogeton pectinatus, etc.), water meal (genus Wolfifia), water mill foils (Myriophyllum s)
aquatic plants such as Picatum, Myriophyllum heterophyllum) and water hyacinth (Eichhornia classesipes). Mosses, moss, hornworts. Cyanobacteria. Ferns. Suckers of perennial crops (fruits, stones, berries, nuts, citrus, hops, grapes, etc.).

Examples of harmful arthropods for which the compounds of the present invention are effective include harmful insects and harmful mites, and specifically the following.
Hemiptera: small brown planthopper (Laodelphax striatellus), brown planthopper (Nilaparvata lugens), planthoppers such as Sejirounka (Sogatella furcifera), green rice leafhopper (Nephotettix cincticeps), Taiwan green rice leafhopper (Nephotettix virescens), tea Roh green leafhopper (Empoasca onukii) such as Leafhoppers, cotton aphids (Aphis gossypii), peaches aphids (Myzus persicae), radish aphids (Brevicoryne brassicae), snowy aphids (Aphis spiraecola), tulip beetle aphids iphum euphorbiae), potato beetle aphid (Aulacorthum solani), wheat leaf aphid (Rhopalosiphum padi), citrus aphid (Tomoptera citricidus), peach beetle Stink bugs such as stink bugs (Riptortus clavetus), spider helicopter bugs (Leptocorina chinensis), bark beetles (Eysarcoris parvus), winged beetles (Haryomorpha mista) m), tobacco whitefly (Bemisia tabaci), silverleaf whitefly (Bemisia argentifolii), mandarin orange whitefly (Dialeurodes citri), whiteflies such as mandarin orange spiny whitefly (Aleurocanthus spiniferus), Acamar scale insects (Aonidiella aurantii), Sanho zero scale insects (Comstockaspis perniciosa ), Citrus snow scale (Unaspis citri), Ruby beetles (Ceroplastes rubens), Icerya purchasi, Fujino scale (Pranococcus kraunhiae), Kuwakonaseura dura coccus longispinis), scale insects such as white peach scale (Pseudaulacaspis pentagona), tingidae class, bed bugs such as bed bugs (Cimex lectularius), psyllid, and the like.

Lepidoptera: rice stem borer (Chilo suppressalis), Sankameiga (Tryporyza incertulas), leaf roller (Cnaphalocrocis medinalis), Watanomeiga (Notarcha derogata), Indian meal moth (Plodia interpunctella), the European corn borer (Ostrinia furnacalis), high Madara Roh moth (Hellula undalis), Japanese medusa such as Shibata toga (Pediasia teterrellus), Spodoptera litura, Spodoptera exigua, Ayuyoto (Pseudaletia septata), Atoga assicae), Agrotis ipsilon, Tamanaginawaba (Prusia nigrisigna), Trichopulsia, Heliotis, Helicoberpa, etc. Leguminova glycinnivorella), Azusa yamashiga (Matsumuraeses azukivivora), Apple wolfberry (Adoxophyces orana moss), Adenophymata (Adoxophane). Fusocopreanus, Cydia pomonella, and other species, Euphoria of the genus Cyptolia, Cypridia isp, etc. Species of the genus Curtis, Suga such as Plutella xylostella, Pterophora gossypiella potato moth (Phthorimaea operculella), etc., White hunter Ti anslucens), webbing clothes moth (Tineola bisselliella) Hirozukoga such as such as,
Thrips of the order Thrips thrips
Diptera: Culex (Culex pipiens pallens), Culex (Culex tritaeniorhynchus), Culex such as Culex quinquefasciatus (Culex quinquefasciatus), Aedes aegypti (Aedes aegypti), Aedes albopictus (Aedes albopictus) Aedes genus such as Anopheles sinensis (Anopheles sinensis), etc. Genus Anopheles, chironomid, housefly (Musca domestica), housefly (Muscina stabulans), etc. (A romyza oryzae), rice Hime leafminer (Hydrellia griseola), tomato leafminer, (Liriomyza sativae), legume leafminer (Liriomyza trifolii), leafminer such as the pea (Chromatomyia horticola), chloropidae such as Inekimoguribae (Chlorops oryzae), melon fly (Dacus cucurbitae), fruit flies such as Ceratitis capitata, fruit flies such as Drosophila, flea flies such as Megaseria spiracularis, Clogmia albib, etc. banus trigonus) Abu such as, biting flies, and the like,

  Coleoptera pests: Western Corn Rootworm (Diabrotica virgifera virgifera), corn rootworm such as southern corn rootworm (Diabrotica undecimpunctata howardi), cupreous chafer (Anomala cuprea), rufocuprea (Anomala rufocuprea), chafers such as Japanese beetle (Popillia japonica) , Weevil (Sitophilus zeamais), Rice weevil (Lissohoptrus oryzophilus), Azuki beetle (Callosobrchuchus chiensis), Ezonocnemus squatium (Echinocnemus squat) Weevil such as Anthonomus grandis, Sphenophorus venatus, Tenebrio molitor, Tribium castorum, Tribium castorum Potato beetles such as Phyllotreta striola), Colorado potato beetle (Leptinotarsa decemlineata), Anthrenus verbasci, Dermestes worm beetles (Dermestes mashulates) Shimbushi (Lasioderma serricorne), Epiracunas such as Epilachna vigintioctopuncta, Lyctus brunneus, Pinus stigma (Anoplophora malasiaca) and other longhorn beetles, click beetles (Agriotes spp.), And the like (Paederus fuscipes),

  Insect pests: Locusta migratoria, Kelly (Gryllotalpa africana), Oxya yezoensis, Oyana japonica, Orogi, etc.

  Lepidoptera: Cat fleas (Ctenocephalides felis), Dog fleas (Ctenocephalides canis), Human fleas (Pulex irritans), Keops mud mines (Xenopsylla cheopes), etc.

  Lice insect pests: Pediculus humanus corporis, Pheasius pubis, Haetopinus eurysternus, Sheep lice (Dalmalinia ovis), Pig lice

  Hymenoptera: Monomorium pharaois, Formica fusca japonica, Ochellelus glove, pistomyr pung. Such as ants, wasps, scallops, bees (Athalia rosae), bees such as Japanese bee (Athalia japonica),

  Cockroach Lepidoptera: German cockroach (Blattella germanica), black cockroach (Periplaneta fuliginosa), American cockroach (Periplaneta americana), Tobi brown cockroach (Periplaneta brunnea), cockroaches such as oriental cockroach (Blatta orientalis), Yamato termite (Reticulitermes speratus), Formosan subterranean termite (Coptopterformsformus), American termite minor (Incitermes minor), Cyptotermes domesticus, Odontotermes formosanus, Kushushi Ali (Neotermes koshunensis), Satsuma termites (Glyptotermes satsumensis), Nakajima termites (Glyptotermes nakajimai), Katan termites (Glyptotermes fuscus), Kodama termites (Glyptotermes kodamai), comb Moto termites (Glyptotermes kushimensis), giant termite (Hodotermopsis japonica), Kou Shu Ye termites (Coptoptermes guangzhoensis), Amami termites (Reticultermes miyatakei), White termites (Reticulitermes flaviceps amamius), Mosquitoes Mont termites (Reticulitermes sp.), Takasago termite (Nasutitermes takasagoensis), Nitobe termites (Pericapritermes nitobei), warrior termite (Sinocapritermes mushae), Reticuliterumes flavipes, Reticulitermes hesperus, Reticulitermes virginicus, Reticulitermes tibialis, Heterotermes aureus, termites such as Zootermopsis nevadensis etc,

  Acarid pests: Tetanychus urticae, Kantawa spider mite (Tetranychus kanzawai), citrus spider mite (Panonychus cituli), mite spider mite (Pantonychus ulmi), spider mite pistula mite (Petrus urticae) Tomato rustic mites (Aculops lycopersici), Chanosabi mites (Calacarus carinatus), Chanogasabi mite (Acaphylla theavagrans), Green moss mite (Eriophys chibaensis), Apple scab mites li) Fushidani such as, dust mite such as Chanohokoridani (Polyphagotarsonemus latus), southern Hime Himehadani such as spider mites (Brevipalpus phoenicis), Kenagahadani such, longicornis (Haemaphysalis longicornis), Yamatochimadani (Haemaphysalis flava), Taiwan Kaku ticks (Dermacentor taiwanicus ), American dock ticks (Dermacentor variabilis), Yamato tick (Ixodes ovatus), Schulz ticks (Ixodes perulcatus), Black legged ticks (Ixodes scapularis), Lone star ticks (Amblyom) ticks such as americanum, Bophilus microplus, Rhipicephalus sanguineus, mite mites such as Octodeces cinotis, abite mites ) Acne mites, Tyrophagus putrescentiae, Spinach mite (Tyrophagus similis), etc., Dermatophagoeses phlogenites Dermatophagoides alcohol such, Hosotsumedani (Cheyletus eruditus), Beetle Tsumedani (Cheyletus malaccensis), Tsumedani such as southern Tsumedani (Cheyletus moorei), house dust mite (Ornithonyssus bacoti), Torisashidani (Ornithonyssus sylvairum), chicken mites such as chicken mites (Dermanyssus gallinae) , Tsutsugamushi such as Leptotrombidium akamushi, spiders such as Chiracanthium japonicum, Latrodictus hasseltii, etc.

Lip and leg class: Geeu (Thereuonema hilgendorfi), Tobizukadeka (Scorpendra subspinipes), etc.
Double leg class: Oxidus gracilis, Akadesde (Nedyopus tambanus), etc.
Isopods: Armadillium vulgare, etc.

  The compound of the present invention can also be used for controlling parasites.

（式中、Ｙ¹はハロゲン又は式ＯＳＯ₂Ｒ¹³（Ｒ¹³はＣ_1-3アルキル基及びフェニル基を表し、これらのＣ_1-3アルキル基及びフェニル基はハロゲンで置換されていてもよく、フェニル基はＣ_1-3アルキル基で置換されていてもよい。）で示される基を表し、Ｒ¹、Ｒ²、Ｒ³、Ｇ、Ｊ、Ｗ¹、Ｗ²は前記と同じ意味を表す。）
該反応は溶媒中で行われる。該反応に使用される溶媒としては、例えば、ベンゼン、トルエン、キシレン等の芳香族炭化水素類；ジエチルエーテル、ジイソプロピルエーテル、ジオキサン、テトラヒドロフラン、ジメトキシエタン等のエーテル類；ジクロロメタン、クロロホルム、１，２−ジクロロエタン等のハロゲン化炭化水素類；アセトン、メチルエチルケトン等のケトン類；アセトニトリル等のニトリル類；酢酸エチル等のエステル類；ジメチルホルムアミド、ジメチルアセトアミド等のアミド類；ジメチルスルホキシド等のスルホキシド類；スルホラン等のスルホン類、及びこれらの混合物が挙げられる。 The compound of the present invention can be produced, for example, by the following production method.
Manufacturing method 1
The compound of the present invention can be produced by reacting a compound represented by the formula (II) with a compound represented by the formula (III).

(Wherein Y ¹ represents halogen or the formula OSO ₂ R ¹³ (R ¹³ represents a C _1-3 alkyl group and a phenyl group, and these C _1-3 alkyl group and phenyl group may be substituted with halogen) And a phenyl group may be substituted with a C _1-3 alkyl group.), And R ¹ , R ² , R ³ , G, J, W ¹ and W ² have the same meaning as described above. To express.)
The reaction is performed in a solvent. Examples of the solvent used for the reaction include aromatic hydrocarbons such as benzene, toluene and xylene; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran and dimethoxyethane; dichloromethane, chloroform, 1,2- Halogenated hydrocarbons such as dichloroethane; Ketones such as acetone and methyl ethyl ketone; Nitriles such as acetonitrile; Esters such as ethyl acetate; Amides such as dimethylformamide and dimethylacetamide; Sulfoxides such as dimethyl sulfoxide; Examples include sulfones and mixtures thereof.

In the reaction, the compound represented by the formula (III) is usually used in an amount of 1 mol or more, preferably 1 to 3 mol per 1 mol of the compound represented by the formula (II).
The reaction is usually performed in the presence of a base. Examples of the base used in the reaction include organic bases such as triethylamine, tripropylamine, pyridine, dimethylaminopyridine, 1,8-diazabicyclo [5.4.0] -7-undecene; sodium hydroxide, hydroxide Examples thereof include inorganic bases such as potassium, calcium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, calcium carbonate, sodium hydride, sodium methylate, sodium ethylate, and t-butoxy potassium. In the reaction, a base is generally used in an amount of 0.5 to 10 mol, preferably 1 to 5 mol, per 1 mol of the compound represented by the formula (II).
The reaction temperature of the reaction is usually -30 to 180 ° C, preferably 0 to 100 ° C. The reaction time is usually 10 minutes to 30 hours.
The progress of the reaction can be confirmed by analyzing a part of the reaction mixture by thin layer chromatography, high performance liquid chromatography or the like. After completion of the reaction, for example, by mixing the reaction mixture and water, extracting with an organic solvent, and drying and concentrating the obtained organic layer, the compound represented by the formula (I), That is, the compound of the present invention can be isolated.
The compound represented by the formula (II) is a known compound or can be produced from a known compound. For example, it can be produced according to the method described in International Publication No. 2009/086041 pamphlet (WO2009 / 086041) or the like.
The compound represented by the formula (III) is a known compound or can be produced from a known compound.

  Each compound produced by the above production method 1 can be isolated and purified by other known means such as concentration, vacuum concentration, extraction, phase transfer, crystallization, recrystallization, chromatography and the like. There are cases where it is possible.

Specific examples of the compound of the present invention are shown below.

1) In the formulas (I ¹ ) to (I ³⁰ ),
G—J is a 3- (4-fluorophenyl) -5-methyl-1H-pyrazol-1-yl group,
Pyridazinone in which W ² is chlorine, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, benzyloxy group, methylthio group, ethylthio group, methylsulfinyl group, methylsulfonyl group or N-phenyl-N-ethoxycarbonylamino group Compound,

2) In the formulas (I ¹ ) to (I ³⁰ ),
G—J is a 3- (4-chlorophenyl) -5-methyl-1H-pyrazol-1-yl group,
Pyridazinone in which W ² is chlorine, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, benzyloxy group, methylthio group, ethylthio group, methylsulfinyl group, methylsulfonyl group or N-phenyl-N-ethoxycarbonylamino group Compound,

3) In the formulas (I ¹ ) to (I ³⁰ ),
GJ is a 3- (4-bromophenyl) -5-methyl-1H-pyrazol-1-yl group,
Pyridazinone in which W ² is chlorine, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, benzyloxy group, methylthio group, ethylthio group, methylsulfinyl group, methylsulfonyl group or N-phenyl-N-ethoxycarbonylamino group Compound,

4) In the formulas (I ¹ ) to (I ³⁰ ),
GJ is a 5-methyl-3- (4-trifluoromethylphenyl) -1H-pyrazol-1-yl group,
Pyridazinone in which W ² is chlorine, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, benzyloxy group, methylthio group, ethylthio group, methylsulfinyl group, methylsulfonyl group or N-phenyl-N-ethoxycarbonylamino group Compound,

5) In the formulas (I ¹ ) to (I ³⁰ ),
G-J is a 3- (4-cyanophenyl) -5-methyl-1H-pyrazol-1-yl group,
Pyridazinone in which W ² is chlorine, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, benzyloxy group, methylthio group, ethylthio group, methylsulfinyl group, methylsulfonyl group or N-phenyl-N-ethoxycarbonylamino group Compound,

6) In the formulas (I ¹ ) to (I ³⁰ ),
G-J is a 3- (4-methoxyphenyl) -5-methyl-1H-pyrazol-1H-yl group,
Pyridazinone in which W ² is chlorine, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, benzyloxy group, methylthio group, ethylthio group, methylsulfinyl group, methylsulfonyl group or N-phenyl-N-ethoxycarbonylamino group Compound,

7) In the formulas (I ¹ ) to (I ³⁰ ),
GJ is a 5-methyl-3- (4-trifluoromethoxyphenyl) -1H-pyrazol-1-yl group,
Pyridazinone in which W ² is chlorine, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, benzyloxy group, methylthio group, ethylthio group, methylsulfinyl group, methylsulfonyl group or N-phenyl-N-ethoxycarbonylamino group Compound,

8) In the formulas (I ¹ ) to (I ³⁰ ),
G-J is a 3- (2-fluorophenyl) -5-methyl-1H-pyrazol-1-yl group,
Pyridazinone in which W ² is chlorine, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, benzyloxy group, methylthio group, ethylthio group, methylsulfinyl group, methylsulfonyl group or N-phenyl-N-ethoxycarbonylamino group Compound,

9) In the formulas (I ¹ ) to (I ³⁰ ),
G—J is a 3- (3-fluorophenyl) -5-methyl-1H-pyrazol-1-yl group,
Pyridazinone in which W ² is chlorine, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, benzyloxy group, methylthio group, ethylthio group, methylsulfinyl group, methylsulfonyl group or N-phenyl-N-ethoxycarbonylamino group Compound,

10) In the formulas (I ¹ ) to (I ³⁰ ),
GJ is a 3- (2-chlorophenyl) -5-methyl-1H-pyrazol-1-yl group,
Pyridazinone in which W ² is chlorine, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, benzyloxy group, methylthio group, ethylthio group, methylsulfinyl group, methylsulfonyl group or N-phenyl-N-ethoxycarbonylamino group Compound,

11) In the formulas (I ¹ ) to (I ³⁰ ),
G-J is a 3- (3-chlorophenyl) -5-methyl-1H-pyrazol-1-yl group,
Pyridazinone in which W ² is chlorine, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, benzyloxy group, methylthio group, ethylthio group, methylsulfinyl group, methylsulfonyl group or N-phenyl-N-ethoxycarbonylamino group Compound,

12) In the formulas (I ¹ ) to (I ³⁰ ),
G-J is a 5-methyl-3- (4-methylphenyl) -1H-pyrazol-1-yl group,
Pyridazinone in which W ² is chlorine, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, benzyloxy group, methylthio group, ethylthio group, methylsulfinyl group, methylsulfonyl group or N-phenyl-N-ethoxycarbonylamino group Compound,

13) In the formulas (I ¹ ) to (I ³⁰ ),
GJ is a 3- (4-ethylphenyl) -5-methyl-1H-pyrazol-1-yl group,
Pyridazinone in which W ² is chlorine, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, benzyloxy group, methylthio group, ethylthio group, methylsulfinyl group, methylsulfonyl group or N-phenyl-N-ethoxycarbonylamino group Compound,

14) In the formulas (I ¹ ) to (I ³⁰ ),
G—J is a 3- (2,4-dichlorophenyl) -5-methyl-1H-pyrazol-1-yl group,
Pyridazinone in which W ² is chlorine, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, benzyloxy group, methylthio group, ethylthio group, methylsulfinyl group, methylsulfonyl group or N-phenyl-N-ethoxycarbonylamino group Compound,

15) In the formulas (I ¹ ) to (I ³⁰ ),
GJ is a 3- (3,4-dichlorophenyl) -5-methyl-1H-pyrazol-1-yl group,
Pyridazinone in which W ² is chlorine, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, benzyloxy group, methylthio group, ethylthio group, methylsulfinyl group, methylsulfonyl group or N-phenyl-N-ethoxycarbonylamino group Compound,

16) formula (I ¹⁾ ~ (I ^30), a G-J is 3- (3,4-difluorophenyl) -5-methyl -1H- pyrazol-1-yl group,
Pyridazinone in which W ² is chlorine, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, benzyloxy group, methylthio group, ethylthio group, methylsulfinyl group, methylsulfonyl group or N-phenyl-N-ethoxycarbonylamino group Compound.

17) In the formulas (I ¹ ) to (I ³⁰ ),
GJ is a 5-ethyl-3- (4-fluorophenyl) -1H-pyrazol-1-yl group,
Pyridazinone in which W ² is chlorine, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, benzyloxy group, methylthio group, ethylthio group, methylsulfinyl group, methylsulfonyl group or N-phenyl-N-ethoxycarbonylamino group Compound,

18) In the formulas (I ¹ ) to (I ³⁰ ),
G—J is a 3- (4-chlorophenyl) -5-ethyl-1H-pyrazol-1-yl group,
Pyridazinone in which W ² is chlorine, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, benzyloxy group, methylthio group, ethylthio group, methylsulfinyl group, methylsulfonyl group or N-phenyl-N-ethoxycarbonylamino group Compound,

19) In the formulas (I ¹ ) to (I ³⁰ ),
G-J is a 3- (4-bromophenyl) -5-ethyl-1H-pyrazol-1-yl group,
Pyridazinone in which W ² is chlorine, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, benzyloxy group, methylthio group, ethylthio group, methylsulfinyl group, methylsulfonyl group or N-phenyl-N-ethoxycarbonylamino group Compound,

20) In the formulas (I ¹ ) to (I ³⁰ ),
G-J is a 5-ethyl-3- (4-trifluoromethylphenyl) -1H-pyrazol-1-yl group,
Pyridazinone in which W ² is chlorine, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, benzyloxy group, methylthio group, ethylthio group, methylsulfinyl group, methylsulfonyl group or N-phenyl-N-ethoxycarbonylamino group Compound,

21) In the formulas (I ¹ ) to (I ³⁰ ),
G-J is a 3- (4-cyanophenyl) -5-ethyl-1H-pyrazol-1-yl group,
Pyridazinone in which W ² is chlorine, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, benzyloxy group, methylthio group, ethylthio group, methylsulfinyl group, methylsulfonyl group or N-phenyl-N-ethoxycarbonylamino group Compound,

22) In the formulas (I ¹ ) to (I ³⁰ ),
GJ is a 5-ethyl-3- (4-methoxyphenyl) -1H-pyrazol-1-yl group,
Pyridazinone in which W ² is chlorine, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, benzyloxy group, methylthio group, ethylthio group, methylsulfinyl group, methylsulfonyl group or N-phenyl-N-ethoxycarbonylamino group Compound,

23) In the formulas (I ¹ ) to (I ³⁰ ),
GJ is a 5-ethyl-3- (4-trifluoromethoxyphenyl) -1H-pyrazol-1-yl group,
Pyridazinone in which W ² is chlorine, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, benzyloxy group, methylthio group, ethylthio group, methylsulfinyl group, methylsulfonyl group or N-phenyl-N-ethoxycarbonylamino group Compound,

24) In the formulas (I ¹ ) to (I ³⁰ ),
GJ is a 5-ethyl-3- (2-fluorophenyl) -1H-pyrazol-1-yl group,
Pyridazinone in which W ² is chlorine, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, benzyloxy group, methylthio group, ethylthio group, methylsulfinyl group, methylsulfonyl group or N-phenyl-N-ethoxycarbonylamino group Compound,

25) In the formulas (I ¹ ) to (I ³⁰ ),
GJ is a 5-ethyl-3- (3-fluorophenyl) -1H-pyrazol-1-yl group,
Pyridazinone in which W ² is chlorine, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, benzyloxy group, methylthio group, ethylthio group, methylsulfinyl group, methylsulfonyl group or N-phenyl-N-ethoxycarbonylamino group Compound,

26) In the formulas (I ¹ ) to (I ³⁰ ),
G-J is a 3- (2-chlorophenyl) -5-ethyl-1H-pyrazol-1-yl group,
Pyridazinone in which W ² is chlorine, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, benzyloxy group, methylthio group, ethylthio group, methylsulfinyl group, methylsulfonyl group or N-phenyl-N-ethoxycarbonylamino group Compound,

27) In the formulas (I ¹ ) to (I ³⁰ ),
GJ is a 3- (3-chlorophenyl) -5-ethyl-1H-pyrazol-1-yl group,
Pyridazinone in which W ² is chlorine, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, benzyloxy group, methylthio group, ethylthio group, methylsulfinyl group, methylsulfonyl group or N-phenyl-N-ethoxycarbonylamino group Compound,

28) In the formulas (I ¹ ) to (I ³⁰ ),
GJ is a 5-ethyl-3- (4-methylphenyl) -1H-pyrazol-1-yl group,
Pyridazinone in which W ² is chlorine, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, benzyloxy group, methylthio group, ethylthio group, methylsulfinyl group, methylsulfonyl group or N-phenyl-N-ethoxycarbonylamino group Compound,

29) In the formulas (I ¹ ) to (I ³⁰ ),
GJ is a 5-ethyl-3- (4-ethylphenyl) -1H-pyrazol-1-yl group,
Pyridazinone in which W ² is chlorine, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, benzyloxy group, methylthio group, ethylthio group, methylsulfinyl group, methylsulfonyl group or N-phenyl-N-ethoxycarbonylamino group Compound,

30) In the formulas (I ¹ ) to (I ³⁰ ),
G-J is a 3- (2,4-dichlorophenyl) -5-ethyl-1H-pyrazol-1-yl group,
Pyridazinone in which W ² is chlorine, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, benzyloxy group, methylthio group, ethylthio group, methylsulfinyl group, methylsulfonyl group or N-phenyl-N-ethoxycarbonylamino group Compound,

31) In the formulas (I ¹ ) to (I ³⁰ ),
G—J is a 3- (3,4-dichlorophenyl) -5-ethyl-1H-pyrazol-1-yl group,
Pyridazinone in which W ² is chlorine, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, benzyloxy group, methylthio group, ethylthio group, methylsulfinyl group, methylsulfonyl group or N-phenyl-N-ethoxycarbonylamino group Compound,

32) In the formulas (I ¹ ) to (I ³⁰ ),
G-J is a 3- (3,4-difluorophenyl) -5-ethyl-1H-pyrazol-1-yl group,
Pyridazinone in which W ² is chlorine, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, benzyloxy group, methylthio group, ethylthio group, methylsulfinyl group, methylsulfonyl group or N-phenyl-N-ethoxycarbonylamino group Compound,

33) In the formulas (I ¹ ) to (I ³⁰ ),
G-J is a 3- (4-fluorophenyl) -5-n-propyl-1H-pyrazol-1-yl group,
Pyridazinone in which W ² is chlorine, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, benzyloxy group, methylthio group, ethylthio group, methylsulfinyl group, methylsulfonyl group or N-phenyl-N-ethoxycarbonylamino group Compound,

34) In the formulas (I ¹ ) to (I ³⁰ ),
G—J is a 3- (4-chlorophenyl) -5-n-propyl-1H-pyrazol-1-yl group,
Pyridazinone in which W ² is chlorine, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, benzyloxy group, methylthio group, ethylthio group, methylsulfinyl group, methylsulfonyl group or N-phenyl-N-ethoxycarbonylamino group Compound,

35) In the formulas (I ¹ ) to (I ³⁰ ),
GJ is a 5-n-propyl-3- (4-trifluoromethylphenyl) -1H-pyrazol-1-yl group,
Pyridazinone in which W ² is chlorine, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, benzyloxy group, methylthio group, ethylthio group, methylsulfinyl group, methylsulfonyl group or N-phenyl-N-ethoxycarbonylamino group Compound,

36) In the formulas (I ¹ ) to (I ³⁰ ),
GJ is a 5-cyclopropyl-3- (4-fluorophenyl) -1H-pyrazol-1-yl group,
Pyridazinone in which W ² is chlorine, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, benzyloxy group, methylthio group, ethylthio group, methylsulfinyl group, methylsulfonyl group or N-phenyl-N-ethoxycarbonylamino group Compound,

37) In the formulas (I ¹ ) to (I ³⁰ ),
GJ is a 3- (4-chlorophenyl) -5-cyclopropyl-1H-pyrazol-1-yl group,
Pyridazinone in which W ² is chlorine, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, benzyloxy group, methylthio group, ethylthio group, methylsulfinyl group, methylsulfonyl group or N-phenyl-N-ethoxycarbonylamino group Compound,

38) In the formulas (I ¹ ) to (I ³⁰ ),
GJ is a 5-cyclopropyl-3- (4-trifluoromethylphenyl) -1H-pyrazol-1-yl group,
Pyridazinone in which W ² is chlorine, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, benzyloxy group, methylthio group, ethylthio group, methylsulfinyl group, methylsulfonyl group or N-phenyl-N-ethoxycarbonylamino group Compound,

39) In the formulas (I ¹ ) to (I ³⁰ ),
GJ is a 4,5-dimethyl-3- (4-fluorophenyl) -1H-pyrazol-1-yl group,
Pyridazinone in which W ² is chlorine, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, benzyloxy group, methylthio group, ethylthio group, methylsulfinyl group, methylsulfonyl group or N-phenyl-N-ethoxycarbonylamino group Compound,

40) In the formulas (I ¹ ) to (I ³⁰ ),
GJ is a 3- (4-chlorophenyl) -4,5-dimethyl-1H-pyrazol-1-yl group,
Pyridazinone in which W ² is chlorine, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, benzyloxy group, methylthio group, ethylthio group, methylsulfinyl group, methylsulfonyl group or N-phenyl-N-ethoxycarbonylamino group Compound,

41) In the formulas (I ¹ ) to (I ³⁰ ),
GJ is a 4,5-dimethyl-3- (4-trifluoromethylphenyl) -1H-pyrazol-1-yl group,
Pyridazinone in which W ² is chlorine, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, benzyloxy group, methylthio group, ethylthio group, methylsulfinyl group, methylsulfonyl group or N-phenyl-N-ethoxycarbonylamino group Compound,

42) In the formulas (I ¹ ) to (I ³⁰ ),
GJ is a 5-ethyl-3- (4-fluorophenyl) -4-methyl-1H-pyrazol-1-yl group,
Pyridazinone in which W ² is chlorine, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, benzyloxy group, methylthio group, ethylthio group, methylsulfinyl group, methylsulfonyl group or N-phenyl-N-ethoxycarbonylamino group Compound,

43) In the formulas (I ¹ ) to (I ³⁰ ),
G—J is a 3- (4-chlorophenyl) -5-ethyl-4-methyl-1H-pyrazol-1-yl group,
Pyridazinone in which W ² is chlorine, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, benzyloxy group, methylthio group, ethylthio group, methylsulfinyl group, methylsulfonyl group or N-phenyl-N-ethoxycarbonylamino group Compound,

44) In the formulas (I ¹ ) to (I ³⁰ ),
GJ is a 5-ethyl-4-methyl-3- (4-trifluoromethylphenyl) -1H-pyrazol-1-yl group,
Pyridazinone in which W ² is chlorine, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, benzyloxy group, methylthio group, ethylthio group, methylsulfinyl group, methylsulfonyl group or N-phenyl-N-ethoxycarbonylamino group Compound.

Hereinafter, the present invention will be described more specifically with reference to production examples, formulation examples, and test examples. However, the present invention is not limited to these examples.
In the production examples, room temperature usually indicates 10 to 30 ° C. ¹ H NMR represents a proton nuclear magnetic resonance spectrum, tetramethylsilane was used as an internal standard, and chemical shift (δ) was expressed in ppm.
The symbols used in the production examples have the following meanings.
CDCl ₃ : deuterated chloroform, s: singlet, d: doublet, t: triplet, m: multiplet, J: coupling constant, Me: methyl group, Et: ethyl group.

Production Example 1
4- [5-ethyl-3- [4- (trifluoromethyl) phenyl] -1H-pyrazol-1-yl] -5-hydroxy-2-methyl-3 (2H) -pyridazinone and tetrahydrofuran (5 mL) To the mixture, 0.15 mL of triethylamine, 0.078 g of chloromethyl ethyl ether and 0.007 g of 4-dimethylaminopyridine were added. The mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (ethyl acetate: hexane = 1: 1) to give 5-ethoxymethoxy-4- [5-ethyl-3- [4- (trifluoromethyl) phenyl] -1H-pyrazole-1 0.21 g of -yl] -2-methyl-3 (2H) -pyridazinone [compound (I-1-1)] was obtained as a white powder.
¹ H NMR (CDCl ₃ ) δ ppm: 1.21 (3H, t, J = 7.2 Hz), 1.29 (3H, t, J = 7.6 Hz), 2.43 to 2.50 (1H, m), 2.57 to 2.67 (1H, m), 3.62 to 3.77 (2H, m), 3.83 (3H, s), 5.14 (1H, d, J = 7. 2 Hz), 5.22 (1H, d, J = 7.2 Hz), 6.58 (1H, s), 7.62 (2H, d, J = 8.0 Hz), 7.91 (2H, d, J = 8.0 Hz), 8.04 (1H, s).

The compounds of the present invention produced according to Production Example 1 are shown in Table 1.

表１の化合物について、¹Ｈ ＮＭＲデータを以下に示す。
化合物（Ｉ−１−２）：
¹Ｈ ＮＭＲ（ＣＤＣｌ₃）δ ｐｐｍ：１．２０（３Ｈ，ｔ，Ｊ＝７．２Ｈｚ），１．２７（３Ｈ，ｔ，Ｊ＝７．６Ｈｚ），２．３９〜２．４９（１Ｈ，ｍ），２．５６〜２．６６（１Ｈ，ｍ），３．６２〜３．７６（２Ｈ，ｍ），３．８２（３Ｈ，ｓ），５．１２（１Ｈ，ｄ，Ｊ＝６．８Ｈｚ），５．２１（１Ｈ，ｄ，Ｊ＝６．８Ｈｚ），６．５０（１Ｈ，ｓ），７．３３（２Ｈ，ｄ，Ｊ＝８．４Ｈｚ），７．３４（２Ｈ，ｄ，Ｊ＝８．４Ｈｚ），８．０２（１Ｈ，ｓ）。

化合物（Ｉ−１−３）：
¹Ｈ ＮＭＲ（ＣＤＣｌ₃）δ ｐｐｍ：１．２８（３Ｈ，ｔ，Ｊ＝７．６Ｈｚ），２．４０〜２．４９（１Ｈ，ｍ），２．５７〜２．６６（１Ｈ，ｍ），３．４６（３Ｈ，ｓ），３．８２（３Ｈ，ｓ），５．０８（１Ｈ，ｄ，Ｊ＝６．８Ｈｚ），５．１７（１Ｈ，ｄ，Ｊ＝６．８Ｈｚ），６．５１（１Ｈ，ｓ），７．３３（２Ｈ，ｄ，Ｊ＝８．４Ｈｚ），７．７４（２Ｈ，ｄ，Ｊ＝８．０Ｈｚ），７．９９（１Ｈ，ｓ）。

化合物（Ｉ−１−４）：
¹Ｈ ＮＭＲ（ＣＤＣｌ₃）δ ｐｐｍ：１．２８（３Ｈ，ｔ，Ｊ＝７．６Ｈｚ），２．４０〜２．５１（１Ｈ，ｍ），２．５６〜２．６６（１Ｈ，ｍ），３．４６（３Ｈ，ｓ），３．８２（３Ｈ，ｓ），５．０７（１Ｈ，ｄ，Ｊ＝６．８Ｈｚ），５．１６（１Ｈ，ｄ，Ｊ＝６．８Ｈｚ），６．４９（１Ｈ，ｓ），７．０５（２Ｈ，ｔ，Ｊ＝８．８Ｈｚ），７．７７（２Ｈ，ｄｄ，Ｊ＝５．６，９．２Ｈｚ），７．９９（１Ｈ，ｓ）。

For the compounds in Table 1, ¹ H NMR data is shown below.
Compound (I-1-2):
¹ H NMR (CDCl ₃ ) δ ppm: 1.20 (3H, t, J = 7.2 Hz), 1.27 (3H, t, J = 7.6 Hz), 2.39 to 2.49 (1H, m), 2.56 to 2.66 (1H, m), 3.62 to 3.76 (2H, m), 3.82 (3H, s), 5.12 (1H, d, J = 6. 8 Hz), 5.21 (1 H, d, J = 6.8 Hz), 6.50 (1 H, s), 7.33 (2 H, d, J = 8.4 Hz), 7.34 (2 H, d, J = 8.4 Hz), 8.02 (1H, s).

Compound (I-1-3):
¹ H NMR (CDCl ₃ ) δ ppm: 1.28 (3H, t, J = 7.6 Hz), 2.40 to 2.49 (1H, m), 2.57 to 2.66 (1H, m) , 3.46 (3H, s), 3.82 (3H, s), 5.08 (1H, d, J = 6.8 Hz), 5.17 (1H, d, J = 6.8 Hz), 6 .51 (1H, s), 7.33 (2H, d, J = 8.4 Hz), 7.74 (2H, d, J = 8.0 Hz), 7.99 (1H, s).

Compound (I-1-4):
¹ H NMR (CDCl ₃ ) δ ppm: 1.28 (3H, t, J = 7.6 Hz), 2.40 to 2.51 (1H, m), 2.56 to 2.66 (1H, m) 3.46 (3H, s), 3.82 (3H, s), 5.07 (1 H, d, J = 6.8 Hz), 5.16 (1 H, d, J = 6.8 Hz), 6 .49 (1H, s), 7.05 (2H, t, J = 8.8 Hz), 7.77 (2H, dd, J = 5.6, 9.2 Hz), 7.99 (1H, s) .

  Next, formulation examples are shown. In addition, a part shows a weight part.

Formulation Example 1
Wetting agent Compound (I-1-2) 50% by weight
Sodium lignin sulfonate 5% by weight
Polyoxyethylene alkyl ether 5% by weight
5% white carbon
Clay 35% by weight
To obtain a wettable powder.
Instead of compound (I-1-2), each wettable powder of compound (I-1-1), (I-1-3) and (I-1-4) is obtained in the same manner.

Formulation Example 2
Granule Compound (I-1-3) 1.5% by weight
2% by weight sodium lignin sulfonate
Talc 40% by weight
Bentonite 56.5% by weight
Are mixed and kneaded and granulated to obtain granules.
Instead of the compound (I-1-3), the respective granules of the compounds (I-1-1), (I-1-2) and (I-1-4) are obtained in the same manner.

Formulation Example 3
Flowable agent Compound (I-1-4) 10% by weight
35% by weight of white carbon containing 50% by weight of polyoxyethylene alkyl ether sulfate ammonium salt
55% by weight of water
Are mixed and finely pulverized by a wet pulverization method to obtain a flowable agent.
Instead of the compound (I-1-4), each flowable agent of the compounds (I-1-1), (I-1-2) and (I-1-3) is obtained in the same manner.

Formulation Example 4
25 parts of compound (I-1-1), 25 parts of any one compound selected from the following group A, 5 parts of sodium lignin sulfonate, 5 parts of polyoxyethylene alkyl ether, 5 parts of white carbon, 35 parts of clay Mix and grind to obtain wettable powder.

Group A:
<Phenoxy fatty acid compound>
2,4-PA, MCP, MCPB, phenothiol, mecoprop, fluroxypyr, triclopyr, clomeprop, naproanilide;
<Benzoic acid compound>
2,3,6-TBA, dicamba, clopyralid, picloram, aminopyralid, quinclorac, quinmerac]];
<Urea compound>
Diuron, linuron, chlortoluron, isoproturon, fluometuron, isouron, tebuthiuron, leuthuron, methabendron (Daimuron), methyl-daimuron;
<Triazine compound>
Atrazine, ametrine, cyanazine, simazine, propazine, simetrin, dimetamethrin, promethine, romethrin, promethine, romethrin. Indaziflam;
<Bipyridinium compound>
Paraquat, diquat;
<Hydroxybenzonitrile compound>
Bromoxynil, ioxynil;
<Dinitroaniline compound>
Pendimethalin, prodiamine, trifluralin;
<Organic phosphorus compounds>
Amiprofos-methyl, butamifos, bensulide, piperophos, anilofos, glyphosate, glufosinate-glufosinate-glufosinate (Bialaphos);
<Carbamate compound>
Di-allate, tri-allate, EPTC, butyrate, bentiocarb, esprocarb, molinate, dimepiperate, swep (Chlorpropham), phenmedifam, phenisopham, pyributicarb, ashram;
<Acid amide compound>
Propanil, propyzamide, bromobutide, etobenzanide]];
Chloroacetanilide herbicidal compounds [acetochlor, alachlor, butachlor, dimethenamide, propachlor, metazachlor or retrachlor , Tenylchlor, petoxamide;
<Diphenyl ether compound>
Aciflufen-sodium, bifenox, oxyfluorfen, lactofen, fomesafen, clomethoxynil, aclonifen;
<Cyclic imide compound>
Oxadiazone, cinidone-ethyl, carfentrazone-ethyl, sulfentrazone, flurochlorac-pentyl, flumioxazine (flumifluaflufen) Ethyl (pyraflufen-ethyl), oxadiaargyl, pentoxazone, fluthiacet-methyl, butafenacil, benzfenzone, carbfenzone saflufenacil);
<Pyrazole compound>
Benzofenap, pyrazolate, pyrazoxifene, topramzone, pyrasulfotole;
<Triketone compound>
Isoxaflutole, benzobicyclon, sulcotrione, mesotrione, tembotrione, tefuryltrione, icylcyclone;
<Aryloxyphenoxypropionic acid compound>
Clodinahop-propargyl, cyhalofop-butyl, diclohop-methyl, phenoxaprop-ethyl, fluodihopbutyl Xyhop-methyl, quizalofop-ethyl, metamihop;
<Trione oxime compound>
Alloxydim-sodium, cetoxydim, butroxydim, clesodim, cloproxidim, cyclohexyloxym, teproloxydim, tepraxiram ;
<Sulfonylurea compound>
Chlorsulfuron, sulfomethuron-methyl, metsulfuron-methyl, chlorimuron-ethyl, tribenuron-methyl, tribenuron-methyl trisulfuron, bensulfuron-methyl, thifensulfuron-methyl, pyrazosulfuron-ethyl, primisulfuron-methylsulfuronyl-methylsulfate (Amidosulfuron), cinosulfuron (imazosulfuron), rimsulfuron (rimsulfuron), halosulfuron-methyl, prosulfuron (methylsulfuron), methulsulfuron (methylsulfuron) triflusulfuron-methyl), flazasulfuron, cyclosulfamuron, flupirsulfuron, sulfosulfuron, azimsulfuron (uronmsulfuron) , Ethoxysulfuron, oxasulfuron, sodium iodosulfuron-methyl-sodium, foramsulfuron, mesosulfuron-methylsulfuron-trisulfuron ), Tritosulfuron, orthosulfamuron, flucetosulfuron, propyrisulfuron, metazosulfuron;
<Imidazolinone compounds>
Imazametabenz-methyl, imazamethapyr, imazamox, imazapyr, imazaquin, imazepy (imazepine);
<Sulfonamide compound>
Flumetslam, metosulam, dicloslam, floraslam, chloranthram-methyl, penoxslam, pyroxsulp
<Pyrimidinyloxybenzoic acid compound>
Pyrithiobac-sodium, Bispyribac-sodium, Pyriminobac-methyl, Pyribenzoxim, Pyriphthalmide, Pyriftalid p
<Other herbicidal compounds>
Bentazone, bromacil, terbacil, chlorthiamid, isoxaben, dinoseb, amitrole, cinmethirin, cinmethirin Diflufenzopyr sodium (diflufenzopyr-sodium), dithiopyr (dithiopyr), thiazopyr (thiazopyr), flucarbazone sodium (flucarbazone-sodium), propoxycarbazonefeneme-nafeneme-soname (s) t), flufenacet, fentrazamide, fentrazamide, caffentrol, indanofan, oxadichromefone, fluidate, lcnidone, frenacet ), Flurtamone, diflufenican, picolinafen, beflubutamide, clomazone, amikacarbazone, pinoxaden (in) aden), pyraclonil, pyroxasulfone, thiencarbazone-methyl, aminocyclopyrazole, ipfencarbazonethiophene, thiophenecarbazoline (thicarbazolone) fenoxasulfone).

Formulation Example 5
1 part of Compound (I-1-2), 1 part of any compound selected from Group A, 2 parts of sodium lignin sulfonate, 40 parts of talc, and 56 parts of bentonite are mixed and mixed with water. Granulate to obtain granules.

Formulation Example 6
5 parts of Compound (I-1-3), 5 parts of any compound selected from Group A, 35 parts of white carbon containing 50% by weight of polyoxyethylene alkyl ether sulfate ammonium salt, and 55 parts of water were mixed. The flowable agent is obtained by fine pulverization by a wet pulverization method.

Formulation Example 7
25 parts of compound (I-1-4), 25 parts of any one compound selected from group A, 5 parts of sodium lignin sulfonate, 5 parts of polyoxyethylene alkyl ether, 5 parts of white carbon, and 35 parts of clay Mix and grind to obtain wettable powder.

Formulation Example 8
1 part of compound (I-1-1), 1 part of any one of compounds selected from the following group B, 2 parts of sodium lignin sulfonate, 40 parts of talc and 56 parts of bentonite are mixed and mixed with water. Granulate to obtain granules.

Group B:
<Drug-damaging compounds>
Benoxacol, cloquintocet-mexyl, ciomethrinil, dichlormid, fenchlorazole-fluyl, fenchlorimol, fenchlorimol. , Mefenpyr-diethyl, MG191, oxabetrinil, aldidochlor, isoxadifen-ethyl, cyprosulfamide, fluxofemide m), 1,8-naphthalic anhydride (1,8-naphthalic anhydride).

Formulation Example 9
5 parts of compound (I-1-2), 5 parts of any one compound selected from the above-mentioned group B, 35 parts of white carbon containing 50% by weight of polyoxyethylene alkyl ether sulfate ammonium salt, and 55 parts of water were mixed. The flowable agent is obtained by fine pulverization by a wet pulverization method.

Formulation Example 10
25 parts of the compound (I-1-3), 25 parts of the compound selected from the above group B, 5 parts of sodium lignin sulfonate, 5 parts of polyoxyethylene alkyl ether, 5 parts of white carbon, and 35 parts of clay are mixed and ground. To obtain a wettable powder.

Formulation Example 11
1 part of Compound (I-1-4), 1 part of any one of the compounds selected from Group B above, 2 parts of sodium lignin sulfonate, 40 parts of talc and 56 parts of bentonite are mixed and mixed with water. Granulate to obtain granules.

Test Example 1-1
A plastic cup having a diameter of 8 cm and a depth of 6.5 cm was filled with soil. Here, oat (Avena fatua) was sown. After the plant grew to the 1st to 2nd leaf stage, a chemical solution containing the compound of the present invention was uniformly sprayed over the whole plant at a predetermined treatment dose. The chemical solution was prepared by dissolving a predetermined amount of the test compound in a dimethylformamide solution (2%) of Tween 20 (polyoxyethylene sorbitan fatty acid ester, manufactured by MP Biomedicals, Inc.) and diluting with deionized water. After the chemical treatment, the plant was cultivated in a greenhouse for 20 days. Thereafter, the efficacy of controlling oats was visually evaluated. Evaluation was shown in 101 steps from 0 (no action) to 100 (complete death).
As a result, Compound (I-1-1) showed an efficacy of 100 at a treatment dose of 8 g / ha. In contrast, Compound A had a potency of 50 at the same treatment dose.

Test Example 1-2
A plastic cup having a diameter of 8 cm and a depth of 6.5 cm was filled with soil. Here, retinochahiki (Bromus sterilis) was seeded. After the plant grew to the 1st to 2nd leaf stage, a chemical solution containing the compound of the present invention was uniformly sprayed over the whole plant at a predetermined treatment dose. The chemical solution was prepared by dissolving a predetermined amount of the test compound in a dimethylformamide solution (2%) of Tween 20 (polyoxyethylene sorbitan fatty acid ester, manufactured by MP Biomedicals, Inc.) and diluting with deionized water. After the chemical treatment, the plant was cultivated in a greenhouse for 20 days. Thereafter, the efficacy of controlling retinochahiki was visually evaluated. Evaluation was shown in 101 steps from 0 (no action) to 100 (complete death).
As a result, the compound (I-1-1) showed a potency of 80 at a treatment dose of 8 g / ha. In contrast, Compound A was potency 10 at the same treatment dose.

試験例１−３
直径８ｃｍ、深さ６．５ｃｍのプラスチックカップに土を充填した。ここにセイヨウヌカボ（Ａｐｅｒａ ｓｐｉｃａ−ｖｅｎｔｉ）を播種した。植物が１〜２葉期まで生育したのち、本発明化合物を含む薬液を所定の処理薬量で植物全体に均一に散布した。薬液は供試化合物の所定量をトゥイーン２０（ポリオキシエチレンソルビタン脂肪酸エステル、ＭＰバイオメディカルズ・インク製）のジメチルホルムアミド溶液（２％）に溶解し、脱イオン水で希釈することにより調製した。薬剤処理後、植物を温室内で２０日間栽培した。その後、セイヨウヌカボ防除の効力を目視評価した。評価は０（無作用）〜１００（完全枯死）の１０１段階で示した。
その結果、化合物（Ｉ−１−３）は４ｇ／ｈａの処理薬量で効力６０を示した。対して、化合物Ｂは同じ処理薬量で効力１０であった。

Test Example 1-3
A plastic cup having a diameter of 8 cm and a depth of 6.5 cm was filled with soil. This was seeded with Apera spica-venti. After the plant grew to the 1st to 2nd leaf stage, a chemical solution containing the compound of the present invention was uniformly sprayed over the whole plant at a predetermined treatment dose. The chemical solution was prepared by dissolving a predetermined amount of the test compound in a dimethylformamide solution (2%) of Tween 20 (polyoxyethylene sorbitan fatty acid ester, manufactured by MP Biomedicals, Inc.) and diluting with deionized water. After the chemical treatment, the plant was cultivated in a greenhouse for 20 days. Thereafter, the efficacy of the control of white croaker was visually evaluated. Evaluation was shown in 101 steps from 0 (no action) to 100 (complete death).
As a result, the compound (I-1-3) showed an efficacy of 60 at a treatment dose of 4 g / ha. In contrast, Compound B was potency 10 at the same treatment dose.

  The compound of the present invention has a weed control effect and a harmful arthropod control effect.

Claims (13)

Formula (I)

(Where
R ¹ is hydrogen, C _1-6 alkyl groups, C _2-6 alkenyl groups, C _2-6 alkynyl, C _1-6 haloalkyl groups, C _2-6 haloalkenyl groups, C _2-6 haloalkynyl groups, C _3-8 cycloalkyl group, C _3-8 halocycloalkyl group, C _4-10 alkyl cycloalkyl group, C _4-10 cycloalkylalkyl group, C _6-14 cycloalkyl cycloalkyl group, C _4-10 halocyclo group _Alkylalkyl group, C _5-12 alkylcycloalkylalkyl group, C _3-8 cycloalkenyl group, C _3-8 halocycloalkenyl group, C _2-8 alkoxyalkyl group, C _4-10 cycloalkoxyalkyl group, C _{3 -10 represents an} alkoxyalkoxyalkyl group, a _C2-8 alkylthioalkyl group, a _C2-8 alkylsulfinylalkyl group, a _C2-8 alkylsulfonylalkyl group or a tetrahydropyranyl group,
R ² is hydrogen, halogen, cyano group, —C (═O) OH, —C (═O) NH ₂ , C _1-6 alkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _{1 -6} haloalkyl group, C _2-6 haloalkenyl group, C _2-6 haloalkynyl group, C _3-8 cycloalkyl group, C _3-8 halocycloalkyl group, C _4-10 alkylcycloalkyl group, C _{4- 10} cycloalkylalkyl group, C _6-14 cycloalkylcycloalkyl group, C _4-10 halocycloalkylalkyl group, C _5-12 alkylcycloalkylalkyl group, C _3-8 cycloalkenyl group, C _3-8 halocyclo Alkenyl group, C _2-8 alkoxyalkyl group, C _4-10 cycloalkoxyalkyl group, C _3-10 alkoxyalkoxyalkyl group, C _2-8 alkylthioalkyl group, C _2-8 alkylsulfinylalkyl group, C _2-8 alkylsulfonyl group, C _2-8 A Job aryloxycarbonyl group, C _4-10 cycloalkoxy group, C _5-12 cycloalkyl alkoxycarbonyl group, C _2-8 alkylaminocarbonyl group, C _3-10 dialkylamino group, C _4-10 cycloalkyl aminocarbonyl Group, C _1-6 alkoxy group, C _1-6 haloalkoxy group, C _1-6 alkylthio group, C _1-6 haloalkylthio group, nitro group, C _3-6 cycloalkoxy group or C _4-8 cycloalkylalkoxy Represents a group,
R ³ represents hydrogen or a C _1-6 alkyl group,
W ¹ represents oxygen or sulfur,
W ² is halogen or the following formula

{Wherein R ⁴ , R ⁵ , R ⁷ , and R ¹¹ are a C _1-6 alkyl group, a C _3-8 cycloalkyl group,
A C _3-6 alkenyl group, a C _3-6 alkynyl group, a phenyl group or a phenyl C _1-6 alkyl group;
R ¹² represents a C _1-6 alkyl group, a C _3-8 cycloalkyl group, a C _3-6 alkenyl group, a C _3-6 alkynyl group, a phenyl group or a phenyl C _1-6 alkyl group,
R ⁶ , R ⁸ , and R ⁹ are a C _1-6 alkyl group, a C _3-8 cycloalkyl group, a C _3-6 alkenyl group, a C _3-6 alkynyl group, a phenyl group, a phenyl C _1-6 alkyl group. A C _1-6 alkoxy group, a C _3-8 cycloalkyloxy group, a C _3-6 alkenyloxy group, a C _3-6 alkynyloxy group, a phenoxy group or a phenyl C _1-6 alkoxy group,
R ¹⁰ represents a C _1-6 alkyl group, a C _3-8 cycloalkyl group, a C _3-6 alkenyl group, a C _3-6 alkynyl group, a phenyl group, a phenyl C _1-6 alkyl group, a C _1-6 alkoxy group. _Represents a C _3-8 cycloalkyloxy group, a C _3-6 alkenyloxy group, a C _3-6 alkynyloxy group, a phenoxy group or a phenyl C _1-6 alkoxy group, or R ⁹ and R ¹⁰ are bonded carbonyl groups. And a 5- or 6-membered cyclic imide group that may be condensed with a benzene ring together with nitrogen,
Here, any group represented by R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ and R ¹² is selected from the group consisting of halogen and C _1-6 alkoxy groups. May be substituted with at least one
The phenyl group represented by R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ and R ¹² and the phenyl moiety of the phenyl C _1-6 alkyl group are all C _{1. Optionally} substituted by a _-6 alkyl group,
Any of the phenoxy group represented by R ⁶ , R ⁸ , R ⁹ and R ¹⁰ and the phenyl moiety of the phenyl C _1-6 alkoxy group may be substituted with a C _1-6 alkyl group,
m represents 0, 1 or 2; } Represents a group represented by
G is a 5- or 6-membered heteroaromatic ring (in the case where the heteroaromatic ring contains at least one nitrogen as a constituent element, the nitrogen may each be substituted with R ^x . The carbon which is a constituent of the above may be substituted with a maximum of 4 substituents independently selected from R ^w ),
J represents a heteroaromatic ring of benzene ring or a 5- or 6-membered ring (Incidentally, the benzene ring and the complex-aromatic ring may be substituted with up to 5 substituents independently selected from R ^u.) ,
Each R ^u is independently halogen, cyano group, hydroxy group, amino group, nitro group, —CHO, —C (═O) OH, —C (═O) NH ₂ , —SO ₂ NH ₂ , SF ₅ , C _1-6 alkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _1-6 haloalkyl group, C _3-8 cycloalkyl group, C _3-8 halocycloalkyl group, C _4-10 alkyl Cycloalkyl group, C _4-10 cycloalkylalkyl group, C _4-10 halocycloalkylalkyl group, C _5-12 alkylcycloalkylalkyl group, C _2-8 alkylcarbonyl group, C _2-8 haloalkylcarbonyl group, C _2-8 alkoxycarbonyl group, C _4-10 cycloalkoxycarbonyl group, C _5-12 cycloalkylalkoxycarbonyl group, C _2-8 alkylaminocarbonyl group, C _3-10 dialkylaminocarbonyl group, C _1-6 alkoxy group , C _1-6 Haroa Kokishi group, C _2-8 alkylcarbonyloxy, C _1-6 alkylthio group, C _1-6 haloalkylthio group, C _1-6 alkylsulfinyl group, C _1-6 haloalkylsulfinyl group, C _1-6 alkylsulfonyl group C _1-6 haloalkylsulfonyl group, C _1-6 alkylaminosulfonyl group, C _2-8 dialkylaminosulfonyl group, C _3-10 trialkylsilyl group, C _1-6 alkylamino group, C _2-8 dialkylamino Group, C _2-8 alkylcarbonylamino group, C _1-6 alkylsulfonylamino group, phenyl group, pyridinyl group or thienyl group,
R ^w is independently halogen, cyano group, hydroxy group, amino group, nitro group, —CHO, —C (═O) OH, —C (═O) NH ₂ , —SO ₂ NH ₂ , SF ₅ , C _1-6 alkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _1-6 haloalkyl group, C _3-8 cycloalkyl group, C _3-8 halocycloalkyl group, C _4-10 alkyl Cycloalkyl group, C _4-10 cycloalkylalkyl group, C _4-10 halocycloalkylalkyl group, C _5-12 alkylcycloalkylalkyl group, C _2-8 alkylcarbonyl group, C _2-8 haloalkylcarbonyl group, C _2-8 alkoxycarbonyl group, C _4-10 cycloalkoxycarbonyl group, C _5-12 cycloalkylalkoxycarbonyl group, C _2-8 alkylaminocarbonyl group, C _3-10 dialkylaminocarbonyl group, C _1-6 alkoxy group , C _1-6 Haroa Kokishi group, C _2-8 alkylcarbonyloxy, C _1-6 alkylthio group, C _1-6 haloalkylthio group, C _1-6 alkylsulfinyl group, C _1-6 haloalkylsulfinyl group, C _1-6 alkylsulfonyl group C _1-6 haloalkylsulfonyl group, C _1-6 alkylaminosulfonyl group, C _2-8 dialkylaminosulfonyl group, C _3-10 trialkylsilyl group, C _1-6 alkylamino group, C _2-8 dialkylamino A group, a C _2-8 alkylcarbonylamino group, a C _1-6 alkylsulfonylamino group or a naphthyl group,
Each R ^x independently represents a C _1-3 alkyl group or a C _3-7 cycloalkyl group. )
A pyridazinone compound represented by: R ¹ is hydrogen, C _1-6 alkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _1-6 haloalkyl group, C _2-6 haloalkenyl group, C _2-6 haloalkynyl group, C _3-8 cycloalkyl group, C _3-8 halocycloalkyl group, C _4-10 alkyl cycloalkyl group, C _4-10 cycloalkylalkyl group, C _6-14 cycloalkyl cycloalkyl group, C _4-10 halocyclo group An _alkylalkyl group, a C _5-12 alkylcycloalkylalkyl group, a C _2-8 alkoxyalkyl group, a C _4-10 cycloalkoxyalkyl group or a C _3-10 alkoxyalkoxyalkyl group,
R ² is hydrogen, halogen, C _1-6 alkyl group, C _1-6 haloalkyl group, C _3-8 cycloalkyl group, C _2-8 alkoxyalkyl group or C _1-4 alkoxy group,
W ² is a C _1-6 alkoxy group,
G is a 5- or 6-membered heteroaromatic ring (in the case where the heteroaromatic ring contains at least one nitrogen as a constituent element, the nitrogen may be substituted with R ^x . The carbon that is a component of the above may be substituted with a maximum of 4 substituents independently selected from R ^w ),
J is an heteroaromatic ring of a benzene ring or a 5- or 6-membered ring (Incidentally, the benzene ring, the complex-aromatic ring may be substituted with up to 5 substituents independently selected from R ^u.) ,
Each R ^u is independently halogen, cyano group, hydroxy group, amino group, nitro group, —CHO, —C (═O) OH, —C (═O) NH ₂ , —SO ₂ NH ₂ , SF ₅ , C _1-6 alkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _1-6 haloalkyl group, C _3-8 cycloalkyl group, C _3-8 halocycloalkyl group, C _2-8 alkyl Carbonyl group, C _2-8 haloalkylcarbonyl group, C _2-8 alkoxycarbonyl group, C _2-8 alkylaminocarbonyl group, C _3-10 dialkylaminocarbonyl group, C _1-6 alkoxy group, C _1-6 haloalkoxy group Group, C _2-8 alkylcarbonyloxy group, C _1-6 alkylthio group, C _1-6 haloalkylthio group, C _1-6 alkylsulfonyl group, C _1-6 haloalkylsulfonyl group, C _1-6 alkylaminosulfonyl group C _2-8 dialkylaminosulfonyl group, C _1-6 alkylamino group, C _2-8 dialkylamino group, C _2-8 alkylcarbonylamino group, C _1-6 alkylsulfonylamino group, phenyl group, pyridinyl group or thienyl group,
R ^w is independently halogen, cyano group, hydroxy group, amino group, nitro group, —CHO, —C (═O) OH, —C (═O) NH ₂ , —SO ₂ NH ₂ , SF ₅ , C _1-6 alkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _1-6 haloalkyl group, C _3-8 cycloalkyl group, C _3-8 halocycloalkyl group, C _4-10 alkyl A cycloalkyl group, a C _4-10 cycloalkylalkyl group, a C _2-8 alkylcarbonyl group, a C _2-8 haloalkylcarbonyl group, a C _2-8 alkoxycarbonyl group, a C _2-8 alkylaminocarbonyl group, a C _3-10 Dialkylaminocarbonyl group, C _1-6 alkoxy group, C _1-6 haloalkoxy group, C _2-8 alkylcarbonyloxy group, C _1-6 alkylthio group, C _1-6 haloalkylthio group, C _1-6 alkylsulfonyl group, C _1-6 haloalkylsulfonyl group, C _1-6 A A Kiruamino group or a C _2-8 dialkylamino group,
Each R ^x is independently hydrogen or a C _1-3 alkyl group,
The pyridazinone compound according to claim 1. R ¹ is hydrogen, a C _1-6 alkyl group, a C _1-6 haloalkyl group or a C _3-8 cycloalkyl group,
R ² is hydrogen, halogen, C _1-6 alkyl group or C _1-4 alkoxy group,
R ³ is hydrogen;
W ¹ is oxygen,
G is a ring selected from:

(Where the bond on the left of the ring represents the bond with the pyridazinone ring of formula (I), the bond on the right represents the bond with J,
t represents 0 or 1,
x represents 0, 1 or 2; )
J is benzene ring optionally substituted by up to 3 substituents independently selected from R ^u,
Each R ^u is independently halogen, cyano group, nitro group, —CHO, —C (═O) OH, C _1-6 alkyl group, C _1-6 haloalkyl group, C _3-8 cycloalkyl group, C _{3 -8} halocycloalkyl group, C _1-6 alkoxy group, C _1-6 haloalkoxy group, C _1-6 alkylamino group, C _2-8 dialkylamino group or phenyl group,
R ^w is independently a halogen, a hydroxy group, a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _3-8 cycloalkyl group, a C _1-6 alkoxy group or a C _1-6 haloalkoxy group. ,
R ^x is hydrogen or a C _1-3 alkyl group,
The pyridazinone compound according to claim 2. R ¹ is hydrogen or a C _1-6 alkyl group,
R ² is hydrogen, chlorine, methyl group, ethyl group or methoxy group;
G is G-12, G-13, G-14, G-15, G-26, G-27, G-28, G-29, G-34, G-35 or G-62;
Each R ^w is independently a halogen or a C _1-6 alkyl group;
J is a benzene ring substituted with a substituent selected from R ^u,
Each R ^u is independently a halogen, a C _1-6 alkyl group or a C _1-6 haloalkyl group,
The pyridazinone compound according to claim 3. R ¹ is a methyl group,
R ² is hydrogen;
G is G-12, G-15, G-26, G-28, G-29, G-34, G-35 or G-62;
Each R ^w is independently a methyl group or an ethyl group;
J is a benzene ring substituted at the para position with a substituent selected independently from R ^u,
R ^u is halogen, a C _1-3 alkyl group or a C _1-3 haloalkyl group,
The pyridazinone compound according to claim 4. R ¹ is a methyl group,
R ² is hydrogen;
W ² is a methoxy group or an ethoxy group,
G is G-26,
x is 1,
R ^w is located at the 5th position of G-26,
R ^u is fluorine, chlorine or a trifluoromethyl group,
The pyridazinone compound according to claim 5. The following pyridazinone compounds according to claim 1.
5-ethoxymethoxy-4- [5-ethyl-3- [4- (trifluoromethyl) phenyl] -1H-pyrazol-1-yl] -2-methyl-3 (2H) -pyridazinone,
4- [3- (4-chlorophenyl) -5-ethyl-1H-pyrazol-1-yl] -5-ethoxymethoxy-2-methyl-3 (2H) -pyridazinone,
4- [3- (4-chlorophenyl) -5-ethyl-1H-pyrazol-1-yl] -5-methoxymethoxy-2-methyl-3 (2H) -pyridazinone,
4- [5-Ethyl-3- (4-fluorophenyl) -1H-pyrazol-1-yl] -5-methoxymethoxy-2-methyl-3 (2H) -pyridazinone.   A herbicide containing the pyridazinone compound according to any one of claims 1 to 7 as an active ingredient.   A method for controlling weeds, wherein an effective amount of the pyridazinone compound according to any one of claims 1 to 7 is applied to weeds or soil where weeds grow.   Use of the pyridazinone compound according to any one of claims 1 to 7 for controlling weeds.   A harmful arthropod control agent comprising the pyridazinone compound according to any one of claims 1 to 7 as an active ingredient.   A method for controlling harmful arthropods, which comprises applying an effective amount of the pyridazinone compound according to any one of claims 1 to 7 to harmful arthropods or habitats of harmful arthropods.   Use of the pyridazinone compound according to any one of claims 1 to 7 for controlling harmful arthropods.