JP2014210806A - Pyridazinone compound and herbicide comprising the same - Google Patents

Abstract

Disclosed is a compound having an excellent control effect against weeds. A pyridazinone compound represented by the formula (I) is a useful compound as an active ingredient of a herbicide. Wherein R 1 represents hydrogen, a C 1-6 alkyl group, a C 3-8 cycloalkyl group, a (C 3-8 cycloalkyl) C 1-6 alkyl group, a C 3-4 alkenyl group or a C 3-4 alkynyl group, and R 2 represents Represents hydrogen, halogen, cyano group, nitro group, C1-6 alkyl group, R3 represents halogen, C1-3 alkyl group, R4 and R5 represent hydrogen and the like, A represents a monocyclic aryl group, etc. G represents a (C1-6 alkyl) carbonyl group, a C1-3 haloalkylcarbonyl group, a (C3-6 cycloalkyl) carbonyl group, a phenylcarbonyl group, a (phenyl) C1-6 alkyl group or a (phenyl) methyl group. ) [Selection figure] None

Description

  The present invention relates to pyridazinone compounds and herbicides containing the same.

Until now, the development of compounds as active ingredients of herbicides for controlling weeds has been advanced, and compounds having weed control efficacy have been found.
Pyridazinone compounds (Patent Documents 1 to 9) having herbicidal activity are known.

International Publication No. 2007/119434 Pamphlet International Publication No. 2009/035150 Pamphlet International Publication No. 2009/086041 Pamphlet International Publication No. 2010/069525 Pamphlet International Publication No. 2010/069526 Pamphlet International Publication No. 2010/078912 Pamphlet International Publication No. 2010/104217 Pamphlet International Publication No. 2010/113986 Pamphlet International Publication No. 2012/091156 Pamphlet

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

〔式中、
Ｒ¹は水素、Ｃ_1-６アルキル基、Ｃ_3-8シクロアルキル基、（Ｃ_3-8シクロアルキル）Ｃ_1-6アルキル基、Ｃ_3-4アルケニル基又はＣ_3-4アルキニル基を表し、
Ｒ²は水素、ハロゲン、シアノ基、ニトロ基、Ｃ_1-6アルキル基、Ｃ_1-6ハロアルキル基、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ハロアルキルチオ基、Ｃ_1-6ハロアルキルスルフィニル基、Ｃ_1-6ハロアルキルスルホニル基、Ｃ_3-8シクロアルキル基、Ｃ_3-8シクロアルコキシ基、（Ｃ_3-8シクロアルキル）Ｃ_1-6アルコキシ基、（Ｃ_1-6アルキルチオ）Ｃ_1-6アルコキシ基、（Ｃ_1-6アルコキシ）Ｃ_1-6アルコキシ基、Ｃ_３-6アルケニルオキシ基、Ｃ_３-6アルキニルオキシ基、シアノＣ_1-6アルコキシ基、（Ｃ_1-6アルコキシ）カルボニルＣ_1-6アルコキシ基、カルバモイルＣ_1-6アルコキシ基、｛（Ｃ_1-6アルキル）アミノカルボニル｝Ｃ_1-6アルコキシ基、｛ジ（Ｃ_1-6アルキル）アミノカルボニル｝Ｃ_1-6アルコキシ基、アミノ基、Ｃ_1-6アルキルアミノ基、ジ（Ｃ_1-6アルキル）アミノ基、ホルミルアミノ基、（Ｃ_1-6アルキル）カルボニルアミノ基、ヒドロキシＣ_1-6アルキル基、（Ｃ_1-6アルコキシ）Ｃ_1-6アルキル基、（Ｃ_1-6ハロアルコキシ）Ｃ_1-6アルキル基、（Ｃ_3-8シクロアルコキシ）Ｃ_1-6アルキル基、｛（Ｃ_3-8シクロアルキル）Ｃ_1-6アルコキシ｝Ｃ_1-6アルキル基、（Ｃ_1-6アルキルチオ）Ｃ_1-6アルキル基、（Ｃ_1-6ハロアルキルチオ）Ｃ_1-6アルキル基、シアノＣ_1-6アルキル基、ヒドロキシイミノＣ_1-6アルキル基、（Ｃ_1-6アルコキシ）イミノＣ_1-6アルキル基、ホルミル基又は（Ｃ_1-6アルキル）カルボニル基を表し、
Ｒ^３はハロゲン、Ｃ_1-3アルキル基、Ｃ_1-3ハロアルキル基、Ｃ_2-4アルケニル基、Ｃ_2-4アルキニル基、Ｃ_1-3アルコキシ基、Ｃ_1-3ハロアルコキシ基又はＣ_3-8シクロアルキル基を表し、
Ｒ^４及びＲ^５は同一又は異なっていてもよく、水素、ハロゲン、Ｃ_1-3アルキル基、Ｃ_1-3ハロアルキル基、Ｃ_2-4アルケニル基、Ｃ_2-4アルキニル基、Ｃ_1-3アルコキシ基、Ｃ_1-3ハロアルコキシ基又はＣ_3-8シクロアルキル基を表し、
Ａは、単環式もしくは二環式縮合環のアリール基を表すか、又はヘテロ原子として窒素、酸素及び硫黄からなる群より選ばれる１以上の原子を含む単環式もしくは二環式縮合環のヘテロアリール基を表し、これらの基はＢ群より選ばれる１以上の原子もしくは基を有していてもよく、
Ｇは下記式

｛式中、Ｒ⁶はＣ_1-6アルキル基、Ｃ_1-3ハロアルキル基、Ｃ_3-6シクロアルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6アルキニル基、Ｃ群より選ばれる１以上の原子もしくは基を有していてもよいＣ_6-10アリール基、（Ｃ群より選ばれる１以上の原子もしくは基を有していてもよいＣ_6-10アリール）Ｃ_1-6アルキル基又は５〜６員のヘテロアリール基を表し、
Ｒ⁷はＣ群より選ばれる１以上の原子もしくは基を有していてもよいフェニル基を表す。｝
で表されるいずれかの基を表す。
Ｂ群：ハロゲン、Ｃ_1-3アルキル基、Ｃ_1-3ハロアルキル基、Ｃ_1-3アルコキシ基、Ｃ_1-3ハロアルコキシ基、Ｃ_3-8シクロアルキル基、Ｃ_2-4アルケニル基、Ｃ_2-4ハロアルケニル基、Ｃ_2-4アルキニル基、Ｃ_1-3アルキルチオ基、Ｃ_1-3ハロアルキルチオ基、Ｃ_1-3アルキルスルフィニル基、Ｃ_1-3ハロアルキルスルフィニル基、Ｃ_1-3アルキルスルホニル基、Ｃ_1-3ハロアルキルスルホニル基、ニトロ基、シアノ基、（Ｃ_1-6アルキル）カルボニル基、（Ｃ_1-6アルコキシ）カルボニル基、カルバモイル基、（Ｃ_1-3アルキル）アミノカルボニル基、ジ（Ｃ_1-3アルキル）アミノカルボニル基、（Ｃ_1-6アルキル）カルボニルアミノ基、（Ｃ_3-8シクロアルキル）カルボニルアミノ基、（Ｃ_1-6アルコキシ）カルボニルアミノ基、及び（Ｃ_1-3アルコキシ）Ｃ_1-3アルキル基からなる群。
Ｃ群：ハロゲン、Ｃ_1-3アルキル基、Ｃ_1-3ハロアルキル基、Ｃ_1-3アルコキシ基及びニトロ基からなる群。〕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。）。 As a result of intensive studies, the present inventors have found that a pyridazinone compound represented by the following formula (I) has an excellent weed control effect, and have reached the present invention.
That is, the present invention is as follows.
(Invention 1) Formula (I)

[Where,
R ¹ represents hydrogen, C _1-6 alkyl group, C _3-8 cycloalkyl group, (C _3-8 cycloalkyl) C _1-6 alkyl group, C _3-4 alkenyl group or C _3-4 alkynyl group. ,
R ² is hydrogen, halogen, cyano group, nitro group, C _1-6 alkyl group, C _1-6 haloalkyl group, C _1-6 alkoxy group, C _1-6 haloalkoxy group, C _1-6 alkylthio group, C _{1-6 1-6} alkylsulfinyl group, C _1-6 alkylsulfonyl group, C _1-6 haloalkylthio group, C _1-6 haloalkylsulfinyl group, C _1-6 haloalkylsulfonyl group, C _3-8 cycloalkyl group, C _{3- 8} cycloalkoxy groups, (C _3-8 cycloalkyl) C _1-6 alkoxy groups, (C _1-6 alkylthio) C _1-6 alkoxy groups, (C _1-6 alkoxy) C _1-6 alkoxy groups, C _{3 -6} alkenyloxy group, C _3-6 alkynyloxy group, cyano C _1-6 alkoxy group, (C _1-6 alkoxy) carbonyl C _1-6 alkoxy group, carbamoyl C _1-6 alkoxy group, {(C _{1- 6} alkyl) amino carbonyl} C _1-6 alkoxy group, {di ( _1-6 alkyl) amino carbonyl} C _1-6 alkoxy group, an amino group, C _1-6 alkylamino group, di (C _1-6 alkyl) amino group, formylamino group, (C _1-6 alkyl) carbonylamino Group, hydroxy C _1-6 alkyl group, (C _1-6 alkoxy) C _1-6 alkyl group, (C _1-6 haloalkoxy) C _1-6 alkyl group, (C _3-8 cycloalkoxy) C _{1- 6} alkyl group, {(C _3-8 cycloalkyl) C _1-6 alkoxy} C _1-6 alkyl group, (C _1-6 alkylthio) C _1-6 alkyl group, (C _1-6 haloalkylthio) C _{1 -6} alkyl group, cyano C _1-6 alkyl group, hydroxyimino C _1-6 alkyl group, (C _1-6 alkoxy) imino C _1-6 alkyl group, formyl group or (C _1-6 alkyl) carbonyl group Represent,
R ³ is halogen, C _1-3 alkyl group, C _1-3 haloalkyl group, C _2-4 alkenyl group, C _2-4 alkynyl group, C _1-3 alkoxy group, C _1-3 haloalkoxy group or C _{3 Represents} an _-8 cycloalkyl group,
R ⁴ and R ⁵ may be the same or different and are hydrogen, halogen, C _1-3 alkyl group, C _1-3 haloalkyl group, C _2-4 alkenyl group, C _2-4 alkynyl group, C _1-3 Represents an alkoxy group, a C _1-3 haloalkoxy group or a C _3-8 cycloalkyl group,
A represents an aryl group of a monocyclic or bicyclic fused ring, or a monocyclic or bicyclic fused ring containing one or more atoms selected from the group consisting of nitrogen, oxygen and sulfur as a hetero atom. Represents a heteroaryl group, and these groups may have one or more atoms or groups selected from group B;
G is the following formula

{Wherein R ⁶ is one or more selected from a C _1-6 alkyl group, a C _1-3 haloalkyl group, a C _3-6 cycloalkyl group, a C _2-6 alkenyl group, a C _2-6 alkynyl group, and a group C. atom or optionally C _6-10 aryl group optionally having a group (one or more atoms optionally C _6-10 aryl optionally having a group selected from group C) C _1-6 alkyl group or Represents a 5-6 membered heteroaryl group,
R ⁷ represents a phenyl group which may have one or more atoms or groups selected from Group C. }
Represents any group represented by
Group B: halogen, C _1-3 alkyl group, C _1-3 haloalkyl group, C _1-3 alkoxy group, C _1-3 haloalkoxy group, C _3-8 cycloalkyl group, C _2-4 alkenyl group, C _2-4 haloalkenyl, C _2-4 alkynyl group, C _1-3 alkylthio group, C _1-3 haloalkylthio group, C _1-3 alkylsulfinyl group, C _1-3 haloalkylsulfinyl group, C _1-3 alkyl Sulfonyl group, C _1-3 haloalkylsulfonyl group, nitro group, cyano group, (C _1-6 alkyl) carbonyl group, (C _1-6 alkoxy) carbonyl group, carbamoyl group, (C _1-3 alkyl) aminocarbonyl group Di (C _1-3 alkyl) aminocarbonyl group, (C _1-6 alkyl) carbonylamino group, (C _3-8 cycloalkyl) carbonylamino group, (C _1-6 alkoxy) carbonylamino group, and (C _1-3 alkoxy) C _1-3 Al The group consisting of Le group.
Group C: a group consisting of halogen, C _1-3 alkyl group, C _1-3 haloalkyl group, C _1-3 alkoxy group and nitro group. ] The pyridazinone compound shown below (it is hereafter described as this invention compound).

(Invention 2) A is a phenyl group, naphthyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, benzothiazolyl group, benzoxazolyl group, quinolinyl group, cinnolinyl group, quinazolinyl group, quinoxalinyl group or benzotriazinyl group These groups may have one or more atoms or groups selected from group B,
As described in (Invention 1), Group B is halogen, C _1-3 alkyl group, C _1-3 haloalkyl group, C _1-3 alkoxy group, C _1-3 haloalkoxy group, nitro group, or cyano group. Pyridazinone compounds.

(Invention 3) R ² is hydrogen, C _1-3 alkyl group, C _1-3 haloalkyl group, C _1-6 alkoxy group, C _1-6 haloalkoxy group, C _3-8 cycloalkyl group, C _3-8 The pyridazinone compound according to (Invention 2), which is a cycloalkoxy group or a (C _3-8 cycloalkyl) C _1-6 alkoxy group.
(Invention 4) The pyridazinone compound according to (Invention 2), wherein R ² is hydrogen, a methyl group or a methoxy group.
(Invention 5) The pyridazinone compound according to (Invention 4), wherein R ¹ is a methyl group.

(Invention 6) R ¹ is a methyl group,
R ² is hydrogen, a methyl group or a methoxy group,
R ³ is a methyl group, an ethyl group, a propyl group, a cyclopropyl group, a halogen or a halomethyl group,
R ⁴ is hydrogen or a methyl group,
R ⁵ is hydrogen, methyl group, ethyl group, propyl group, cyclopropyl group, halogen or halomethyl group,
A is a phenyl group, naphthyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, benzothiazolyl group, benzoxazolyl group, quinolinyl group, cinnolinyl group, quinazolinyl group, quinoxalinyl group or benzotriazinyl group, these The group may have one or more atoms or groups selected from group B,
G may have (C _1-6 alkyl) carbonyl group, C _1-3 haloalkylcarbonyl group, (C _3-6 cycloalkyl) carbonyl group, phenyl optionally having one or more atoms or groups selected from group D It may have a carbonyl group, (phenyl _optionally having one or more atoms or groups selected from group D) C _1-6 alkyl group, or (one or more atoms or groups selected from group D). Phenyl) methyl group,
The pyridazinone compound according to (Invention 1), wherein Group D is halogen, a C _1-3 alkyl group, a C _1-3 haloalkyl group, a C _1-3 alkoxy group, a nitro group, or a cyano group.
(Invention 7) A is a pyridyl group, benzothiazolyl group, benzoxazolyl group, or quinolinyl group, and these groups may have one or more atoms or groups selected from Group B (Invention 6). ) Pyridazinone compounds described.
(Invention 8) R ³ is a methyl group, an ethyl group, a propyl group, a cyclopropyl group,
R ⁴ and R ⁵ are hydrogen,
A is a pyridyl group, a benzothiazolyl group, a benzoxazolyl group, or a quinolinyl group, and these groups may have one or more atoms or groups selected from Group B, and the pyridazinone described in (Invention 6) Compound.

(Invention 9) A herbicide containing the pyridazinone compound according to any one of (Invention 1) to (Invention 8) as an active ingredient.
(Invention 10) A method for controlling weeds, wherein an effective amount of the pyridazinone compound according to any one of (Invention 1) to (Invention 8) is applied to weeds or soil where weeds grow.
(Invention 11) Use of the pyridazinone compound according to any one of (Invention 1) to (Invention 8) for controlling weeds.

  The compound of the present invention has a weed control effect and is effective as an active ingredient of a herbicide.

The substituent in the present invention will be described.
Examples of the halogen include fluorine, chlorine, bromine and iodine.
The C _1-3 alkyl group means an alkyl group having 1 to 3 carbon atoms, and examples thereof include a methyl group, an ethyl group, a normal propyl group, and an isopropyl group.
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 halomethyl group means a methyl group having a halogen such as fluorine, chlorine, bromine or iodine, and examples thereof include a trifluoromethyl group, a difluoromethyl group, a bromomethyl group and a chloromethyl group.
C _1-3 haloalkyl group means an alkyl group having 1 to 3 carbon atoms having a halogen such as fluorine, chlorine, bromine, iodine, etc., for example, trifluoromethyl group, chloromethyl group, 2,2-difluoroethyl Groups, 2,2,2-trichloroethyl group, 2,2,2-trifluoroethyl group and 2,2,2-trifluoro-1,1-dichloroethyl group.
The C _1-6 haloalkyl group means an alkyl group having 1 to 6 carbon atoms having a halogen such as fluorine, chlorine, bromine or iodine, and examples thereof include a trifluoromethyl group, a chloromethyl group, and 2,2-difluoroethyl. Group, 2,2,2-trichloroethyl group, 2,2,2-trifluoroethyl group, 2,2,2-trifluoro-1,1-dichloroethyl group and 2,2-difluorohexyl group. .
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.
(C _3-8 cycloalkyl) C _1-6 alkyl group means an alkyl group having 1 to 6 carbon atoms having a cycloalkyl group having 3 to 8 carbon atoms, such as a cyclopropylmethyl group and a cyclopentylmethyl group. Is mentioned.
The C _2-4 alkenyl group means an alkenyl group having 2 to 4 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 _3-4 alkenyl group means an alkenyl group having 3 to 4 carbon atoms, and examples thereof include an allyl group, a 1-buten-3-yl group, and a 3-buten-1-yl group.
The C _2-4 alkynyl group means an alkynyl group having 2 to 4 carbon atoms, and examples thereof include an ethynyl group, a propargyl group, and a 2-butynyl group.
The C _3-4 alkynyl group means an alkynyl group having 3 to 4 carbon atoms, and examples thereof include a propargyl group and a 2-butynyl group.
The C _1-3 alkoxy group means an alkoxy group having 1 to 3 carbon atoms, and examples thereof include a methoxy group, an ethoxy group, a normal propyloxy group, and an isopropyloxy group.
C _1-6 alkoxy group means an alkoxy group having 1 to 6 carbon atoms, such as methoxy group, ethoxy group, normal propyloxy group, isopropyloxy group, normal butoxy group, isobutoxy group, sec-butoxy group, Examples thereof include a tert-butoxy group, a normal pentoxy group, a sec-pentoxy group, an isopentoxy group, a neopentoxy group, a normal hexyloxy group, and an isohexyloxy group.
The C _1-3 haloalkoxy group means a C _1-3 alkoxy group having a halogen such as fluorine, chlorine, bromine, iodine, etc., and examples thereof include a trifluoromethoxy group, a 2,2-difluoroethoxy group, 2 2,2-trifluoroethoxy group, 2,2,2-trichloroethoxy group, and 3,3-difluoropropyloxy group.
The C _1-6 haloalkoxy group means an alkoxy group having 1 to 3 carbon atoms having halogen such as fluorine, chlorine, bromine, iodine, etc., for example, trifluoromethoxy group, 2,2-difluoroethoxy group, 2 2,2-trifluoroethoxy group, 2,2,2-trichloroethoxy group, 3,3-difluoropropyloxy group and 6-fluorohexyloxy group.
The C _1-6 alkylthio group means an alkylthio group having 1 to 6 carbon atoms, and examples thereof include a methylthio group, an ethylthio group, and an isopropylthio group.
The C _1-6 alkylsulfinyl group means an alkylsulfinyl group having 1 to 6 carbon atoms, and examples thereof include a methylsulfinyl group, an ethylsulfinyl group, and an isopropylsulfinyl group.
The C _1-6 alkylsulfonyl group means an alkylsulfonyl group having 1 to 6 carbon atoms, and examples thereof include a methylsulfonyl group, an ethylsulfonyl group, and an isopropylsulfonyl group.
The C _1-6 haloalkylthio group means an alkylthio group having 1 to 6 carbon atoms having a halogen such as fluorine, chlorine, bromine or iodine, and examples thereof include a trichloromethylthio group, a trifluoromethylthio group, 2,2- Examples thereof include a difluoroethylthio group, a 2,2,2-trifluoroethylthio group, a 2,2,2-trichloroethylthio group, and a 3-chloropropylthio group.
The C _1-6 haloalkylsulfinyl group means an alkylsulfinyl group having 1 to 6 carbon atoms having a halogen such as fluorine, chlorine, bromine or iodine, and includes, for example, a trichloromethylsulfinyl group, a trifluoromethylsulfinyl group, 2 , 2-difluoroethylsulfinyl group, 2,2,2-trifluoroethylsulfinyl group, 2,2,2-trichloroethylsulfinyl group and 3-chloropropylsulfinyl group.
The C _1-6 haloalkylsulfonyl group means a C _1-6 alkylsulfonyl group having a halogen such as fluorine, chlorine, bromine, iodine, etc., and examples thereof include a trichloromethylsulfonyl group, a trifluoromethylsulfonyl group, 2, Examples include 2-difluoroethylsulfonyl group, 2,2,2-trifluoroethylsulfonyl group, 2,2,2-trichloroethylsulfonyl group and 3-chloropropylsulfonyl group.
The C _3-8 cycloalkoxy group means a C _3-8 cycloalkoxy group, and examples thereof include a cyclopropyloxy group, a cyclopentyloxy group, and cyclohexyloxy.
(C _3-8 cycloalkyl) C _1-6 alkoxy group means a C _1-6 alkoxy group having a C _3-8 cycloalkyl group, such as a cyclopropylmethoxy group, 1-cyclo Examples include propylethoxy group and cyclopentylmethoxy group.
(C _1-6 alkylthio) C _1-6 alkoxy group means a C _1-6 alkoxy group bonded to a C _1-6 alkylthio group. For example, a methylthiomethoxy group, a methylthioethoxy group, a methylthio group Examples include a propoxy group, an ethylthiomethoxy group, and an ethylthioethoxy group.
(C _1-6 alkoxy) means a C _1-6 alkoxy group, a C _1-6 alkoxy group bonded to a C _1-6 alkoxy group, such as a methoxymethoxy group, ethoxymethoxy group, normal propyloxy Examples include methoxy group, isopropyloxymethoxy group, 2-methoxyethoxy group, 2-ethoxyethoxy group, and 3-methoxypropyloxy 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 2-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 cyano C _1-6 alkoxy group means a C _1-6 alkoxy group having a cyano group, such as a cyanomethoxy group, a 1-cyanomethoxy group, a 2-cyanoethoxy group, and a 3-cyanopropyloxy group. Is mentioned.
(C _1-6 alkoxy) carbonyl C _1-6 alkoxy group means a C _1-6 alkoxy group bonded to a carbonyl group having (C _1-6 alkoxy group), for example, methoxy Examples thereof include a carbonylmethoxy group and an ethoxycarbonylmethoxy group.
The carbamoyl C _1-6 alkoxy group means a C _1-6 alkoxy group having a carbamoyl group, and examples thereof include a carbamoylmethoxy group.
{(C _1-6 alkyl) aminocarbonyl} C _1-6 alkoxy group means a C _1-6 alkoxy group bonded to (an aminocarbonyl group having a C _1-6 alkyl group); An example is a methylaminocarbonylmethoxy group.
{Di (C _1-6 alkyl) aminocarbonyl} C _1-6 alkoxy group is bonded to {(carbonyl group bonded to two identical or different alkyl groups having 1 to 6 carbon atoms)} Means an alkoxy group having 1 to 6 carbon atoms, and examples thereof include a dimethylaminocarbonylmethoxy group.
The C _1-6 alkylamino group means an alkylamino group having 1 to 6 carbon atoms, and examples thereof include a methylamino group, an ethylamino group, and an isopropylamino group.
The di (C _1-6 alkyl) amino group means an amino group having two identical or different alkyl groups having 1 to 6 carbon atoms, and examples thereof include a dimethylamino group, a diethylamino group, and an ethylmethylamino group. It is done.
The (C _1-6 alkyl) carbonylamino group means an amino group bonded to a carbonyl group having an alkyl group having 1 to 6 carbon atoms, and examples thereof include an acetamido group and a propionylamino group.
The hydroxy C _1-6 alkyl group means a C _1-6 alkyl group having a hydroxyl group, and examples thereof include a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, and a 3-hydroxypropyl group. Can be mentioned.
(C _1-6 alkoxy) C _1-6 alkyl group means an alkyl group having 1 to 6 carbon atoms bonded to an alkoxy group having 1 to 6 carbon atoms, and examples thereof include a methoxymethyl group and 1-methoxyethyl group. Group, ethoxymethyl group, butoxymethyl group and 2-ethoxyethyl group.
(C _1-6 haloalkoxy) C _1-6 alkyl group is an alkyl group having 1 to 6 carbon atoms bonded to (an alkoxy group having 1 to 6 carbon atoms having a halogen such as fluorine, chlorine, bromine or iodine). For example, 2,2-difluoroethoxymethyl group, 2,2,2-trifluoroethoxymethyl group, 2,2-difluoroethoxyethyl group and 2,2,2-trifluoroethoxyethyl group .
(C _3-8 cycloalkoxy) C _1-6 alkyl group means an alkyl group having 1 to 6 carbon atoms bonded to a cycloalkoxy group having 3 to 8 carbon atoms, such as a cyclopropyloxymethyl group and cyclopentyl. An oxymethyl group is mentioned.
{(C _3-8 cycloalkyl) C _1-6 alkoxy} C _1-6 alkyl group is bonded to {(C _1-6 alkoxy group bonded to C _3-8 cycloalkyl group)}. Means an alkyl group having 1 to 6 carbon atoms, and examples thereof include a cyclopropylmethoxymethyl group.
(C _1-6 alkylthio) C _1-6 alkyl group means an alkyl group having 1 to 6 carbon atoms bonded to an alkylthio group having 1 to 6 carbon atoms, such as a methylthiomethyl group, 1- (methylthio) Examples thereof include an ethyl group, an ethylthiomethyl group, a butylthiomethyl group, and a 2- (ethylthio) ethyl group.
(C _1-6 haloalkylthio) C _1-6 alkyl group is an alkyl group having 1 to 6 carbon atoms which is bonded to (an alkylthio group having 1 to 6 carbon atoms having a halogen such as fluorine, chlorine, bromine or iodine). And examples thereof include a trifluoromethylthiomethyl group, a 2,2-difluoroethylthiomethyl group, and a 2,2,2-trifluoroethylthiomethyl group.
The cyano C _1-6 alkyl group means a C _1-6 alkyl group having a cyano group, and examples thereof include a cyanomethyl group, a 1-cyanoethyl group, a 2-cyanoethyl group, and a 3-cyanoethyl group.
The hydroxyimino C _1-6 alkyl group means a C _1-6 alkyl group having a hydroxyimino group, and examples thereof include a hydroxyiminomethyl group.
The (C _1-6 alkoxy) imino C _1-6 alkyl group means an alkyl group having 1 to 6 carbon atoms bonded to an imino group bonded to (an alkoxy group having 1 to 6 carbon atoms), for example, methoxy Examples include iminomethyl group and ethoxyiminomethyl group.
The (C _1-6 alkyl) carbonyl group means a carbonyl group bonded to an alkyl group having 1 to 6 carbon atoms, and examples thereof include an acetyl group, a propionyl group, and a butyryl group.
Examples of the monocyclic or bicyclic condensed ring aryl group include a 5- or 6-membered monocyclic aryl group, or a 6-6-membered or 6-5-membered bicyclic fused ring aryl group, Examples thereof include a phenyl group, a naphthyl group, an indanyl group, and a 1,2,3,4-tetrahydronaphthyl group.
A heteroaryl group of a monocyclic or bicyclic fused ring containing one or more atoms selected from the group consisting of nitrogen, oxygen and sulfur as a heteroatom is a heteroatom selected from the group consisting of nitrogen, oxygen and sulfur. , Means a heterocyclic group containing up to 3 monocyclic, up to 4 bicyclic fused rings, 5 or 6 membered monocyclic heteroaryl group, or 6-6 or 6-5 A heteroaryl group of a membered bicyclic fused ring, such as a furyl group, a thienyl group, a pyrrolyl group, a pyrazolyl group, an imidazolyl group, a 1,2,3-triazolyl group, a 1,2,4-triazolyl group, Oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, 1,2,4-oxadiazolyl group, 1,3,4-oxadiazolyl group, 1,2,5-oxadiazolyl group, 1,2 3-thiadiazolyl group, 1,2,4-thiadiazolyl group, 1,3,4-thiadiazolyl group, 1,2,5-thiadiazolyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, 1,2,3- Triazinyl group, 1,2,4-triazinyl group, indolinyl group, isoindolinyl group, coumarinyl group, 1,3,5-triazinyl group, benzofuryl group, benzisofuryl group, benzothienyl group, benzisothienyl group, indolyl group, Isoindolyl group, indazolyl group, benzothiazolyl group, benzisothiazolyl group, benzoxazolyl group, benzimidazolyl group, 2,1,3-benzoxadiazole group, quinolinyl group, isoquinolinyl group, cinnolinyl group, phthalazinyl group, quinazolinyl Group, quinoxalinyl group, naphthylidini Group, benzotriazinyl, purinyl, and pteridinyl groups, and indolizinyl.
The C _3-6 cycloalkyl group means a cycloalkyl group having 3 to 6 carbon atoms, and examples thereof include a cyclopropyl group, a cyclopentyl group, and a cyclohexyl 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 _6-10 aryl group means an aryl group having 6 to 10 carbon atoms, and examples thereof include a phenyl group and a naphthyl group.
(C _6-10 aryl) C _1-6 alkyl group means an alkyl group having 1 to 6 carbon atoms bonded to an aryl group having 6 to 10 carbon atoms, and examples thereof include a benzyl group and a phenethyl group. .
The 5- to 6-membered heteroaryl group means an aromatic 5- or 6-membered heterocyclic group containing 1 to 3 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur. Examples include a pyridyl group, a 3-thienyl group, and a 1-pyrazolyl group.
The C _2-4 haloalkenyl group means an alkenyl group having 2 to 4 carbon atoms having halogen such as fluorine, chlorine, bromine, iodine, etc., for example, 2,2-difluorovinyl group and 2,2 -A dichlorovinyl group is mentioned.
The C _1-3 alkylthio group means an alkylthio group having 1 to 3 carbon atoms, and examples thereof include a methylthio group, an ethylthio group, and a propylthio group.
C _1-3 haloalkylthio group means an alkylthio group having 1 to 6 carbon atoms having halogen such as fluorine, chlorine, bromine, iodine, etc., for example, trichloromethylthio group, trifluoromethylthio group, 2,2-difluoro Examples thereof include an ethylthio group, a 2,2,2-trifluoroethylthio group, a 2,2,2-trichloroethylthio group, and a 3-chloropropylthio group.
The C _1-3 alkylsulfinyl group means an alkylsulfinyl group having 1 to 3 carbon atoms, and examples thereof include a methylsulfinyl group, an ethylsulfinyl group, and a propylsulfinyl group.
The C _1-3 haloalkylsulfinyl group means an alkylsulfinyl group having 1 to 3 carbon atoms having a halogen such as fluorine, chlorine, bromine or iodine, and examples thereof include a trifluoromethylsulfinyl group.
The C _1-3 alkylsulfonyl group means an alkylsulfonyl group having 1 to 3 carbon atoms, and examples thereof include a methylsulfonyl group, an ethylsulfonyl group, and an isopropylsulfonyl group.
C _1-3 haloalkylsulfonyl group means a C1-C6 alkylsulfonyl group having a halogen such as fluorine, chlorine, bromine, iodine, etc., for example, trichloromethylsulfonyl group, trifluoromethylsulfonyl group, 2, Examples include 2-difluoroethylsulfonyl group, 2,2,2-trifluoroethylsulfonyl group, 2,2,2-trichloroethylsulfonyl group and 3-chloropropylsulfonyl group.
The (C _1-6 alkoxy) carbonyl group means a carbonyl group bonded to (C _1-6 alkoxy group), and examples thereof include a methoxycarbonyl group, an ethoxycarbonyl group, and a normal hexyloxycarbonyl group.
The (C _1-3 alkyl) aminocarbonyl group means a carbonyl group bonded to an amino group having (alkyl group having 1 to 3 carbon atoms), and examples thereof include a methylaminocarbonyl group.
The di (C _1-3 alkyl) aminocarbonyl group means a carbonyl group bonded to an amino group having two identical or different alkyl groups having 1 to 3 carbon atoms, and examples thereof include a dimethylaminocarbonyl group. .
The (C _3-8 cycloalkyl) carbonylamino group means a carbonylamino group bonded to (a cycloalkyl group having 3 to 8 carbon atoms), and examples thereof include a cyclopropylcarbonylamino group and a cyclohexylcarbonylamino group. .
The (C _1-6 alkoxy) carbonylamino group means a carbonylamino group bonded to (an alkoxy group having 1 to 6 carbon atoms), and examples thereof include a methoxycarbonylamino group.
(C _1-3 alkoxy) C _1-3 alkyl group means an alkyl group having 1 to 3 carbon atoms bonded to (an alkoxy group having 1 to 3 carbon atoms), for example, a methoxymethyl group, 1-methoxy Examples include an ethyl group, an ethoxymethyl group, and a 2-ethoxyethyl group.

  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.

  The herbicide of the present invention contains the compound of the present invention and an inert carrier. Examples of the inert carrier include a solid carrier, a liquid carrier, and a gas carrier. The herbicide of the present invention is usually further added with formulation adjuvants such as surfactants, sticking agents, dispersants, stabilizers, etc., wettable powder, wettable powder, flowable powder, granules, dry flowable powder, It is formulated into emulsions, aqueous liquids, oils, smokes, aerosols, microcapsules and the like. The herbicide of the present invention usually contains 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 (for example, N, N-dimethylformamide (hereinafter referred to as DMF), dimethylacetamide), halogenated hydrocarbons (for example, dichloroethane, trichloroethylene, carbon tetrachloride) and the like. It is done.

  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 a place where weeds or weeds will or will 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 will grow or will grow, and the present invention. And a method of treating the herbicide of the present invention with the surface water of a paddy field flooded in a place where the weeds will grow or will grow. 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 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, hops, etc.
Vegetables: Eggplant vegetables (eggplants, tomatoes, peppers, peppers, potatoes, etc.), cucurbits vegetables (cucumbers, pumpkins, zucchini, watermelons, melons, cucumbers, etc.), cruciferous vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage) , Cabbage, mustard, broccoli, cauliflower, etc.), asteraceae vegetables (burdock, garlic, artichoke, lettuce, etc.), liliaceae vegetables (leek, onion, garlic, asparagus, etc.), celery family vegetables (carrot, parsley, celery, American Bow Fu etc.), Rubiaceae vegetables (spinach, chard, etc.), Lamiaceae vegetables (silla, mint, basil etc.), legumes (peas, kidney beans, azuki bean, broad beans, chickpea etc.), strawberries, sweet potatoes, yam, taro , Konjac, ginger, ok Etc..
Fruit trees: fruits (apples, pears, pears, quince, quince, etc.), nuclear fruits (peaches, plums, nectarines, umes, sweet cherry, apricots, prunes, etc.), citrus (citrus mandarin orange, lemon, lime, grapefruit) ), 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, eustoma, etc.), roadside trees (ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple, oak) , Poplar, redwood, fu, sycamore, zelkova, black beetle, Japanese cypress, Japanese cypress, pine, spruce, yew, elm, cypress, etc.), coral jug, dogwood, cedar, cypress, croton, masaki, kanamochi.
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, danchiku, kenaf, cassava, willow, etc.), houseplants, etc.

  The “plant” includes a genetically modified plant.

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

Examples of the active ingredients of such herbicides include the following.
(1) Phenoxy fatty acid herbicidal compound 2,4-PA, MCP, MCPB, phenothiol, mecoprop, fluroxypyr, triclopyr, clomeprop, naproanilide (a) ;
(2) Benzoic acid herbicidal compound 2,3,6-TBA, dicamba, clopyralid, picloram, aminopyralid, quinclorac, quinmerac, etc .;
(3) Urea herbicidal compounds diuron, linuron, chlortoluron, isoproturon, fluometuron, isouron, tebuthiuron, tebuthiuron, tebuthiuron, tebuthiuron ), Cumyluron, daimuron, methyl-daimuron, etc .;
(4) Triazine-based herbicidal compounds atrazine, ametrine, cyanazine, simazine, propazine, simethrin, dimetamethrin (methymethrin) metribuzin), triaziflam, indaziflam and the like;
(5) Bipyridinium-based herbicidal compounds paraquat, diquat, etc .;
(6) Hydroxybenzonitrile-based herbicidal compounds bromoxynil, ioxynil and the like;
(7) Dinitroaniline herbicidal compound pendimethalin, prodiamine, trifluralin, etc .;
(8) Organophosphorus herbicidal compounds amiprofos-methyl, butamifos, bensulide, piperophos, anilofos, glyphosate, glufosinate, glufosinate, glufosinate -P (glufosinate-P), bialaphos, etc .;
(9) Carbamate-based herbicidal compounds: di-allate, tri-allate, EPTC, butyrate, benthocarb, esprocarb, molinate, dimepiperate Swep, chlorprofam, phenmedifam, phenisopham, pyributicalcarb, ashram, etc .;
(10) Acid amide-based herbicidal compound propanil, propyzamide, bromobutide, etobenzanide and the like;
(11) Chloroacetanilide-based herbicidal compounds acetochlor, alachlor, butachlor, dimethylenamide, propachlor, metazachlor, and latrachlor (Pretilachor), tenylchlor, petoxamide and the like;
(12) Diphenyl ether-based herbicidal compounds aciflufen-sodium, bifenox, oxyfluorfen, lactofen, fomesafen, clomethoxenifen, chloromethoxypheny;
(13) Cyclic imide-based herbicidal compounds oxadiazon, cinidone-ethyl, carfentrazone-ethyl, sulfentrazone, full-microlac-pentyl, Flumioxazin, pyraflufen-ethyl, oxadiaargyl, pentoxazone, fluthiacet-methyl, butafenzene, butafenzene bencar azone), saflufenacil (saflufenacil) and the like;
(14) pyrazole herbicidal compounds benzofenap, pyrazolate, pyrazoxifene, topramzone, pyrasulfotole and the like;
(15) Triketonic herbicidal compounds isoxaflutole, benzobicyclon, sulcotrione, mesotrione, tembotrione, tefriltrione, tefuryltricone )etc;
(16) Aryloxyphenoxypropionic acid herbicidal compound clodinafop-propargyl, cyhalohop-butyl, diclohop-methyl, phenoxaprop-ethyl , Fluazifop-butyl, haloxyhop-methyl, quizalofop-ethyl, metamihop, etc .;
(17) Trionoxime herbicidal compounds alloxydim-sodium, cetoxydim, butoxydim, crestodim, cloproxidim, cyclohexyloxydim Tralcoxydim, profoxydim, etc .;
(18) Sulfonylurea-based herbicidal compounds chlorsulfuron, sulfomethuron-methyl, metsulfuron-methyl, chlorimuron-ethyl, tribenuron methyl (Tribenuron-methyl), triasulfuron (triasulfuron), bensulfuron-methyl, thifensulfuron-methyl, pyrazosulfuron-thylfuryl-urmethyl-uryl Nicosulfuron (nic sulfuron, amidosulfuron, cinosulfuron, imazosulfuron, rimsulfuron, halosulfuron-thursulfuron (thulsulfuron), prosulfuron , Triflusulfuron-methyl, flazasulfuron, cyclosulfamuron, flupirsulfuron, sulfosulfuron, azym Ruflon, ethoxysulfuron, oxasulfuron, iodosulfuron-methyl-sodium, foramsulfuron, mesosulfuron, mesosulfuron Cisulfuron, tritosulfuron, orthosulfamuron, flucetosulfuron, propyrisulfuron, metazosulfuron, methazosulfuron Fensulfuron-sodium, etc .;
(19) imidazolinone-based herbicidal compound imazametabenz-methyl, imazamox, imazapic, imazapyr, imazaquin (imazapir)
(20) Sulfonamide-based herbicidal compounds flumetslam, metosulam, dicloslam, floraslam, chloranthramx, penoxsulx, penoxsulx, penoxsulx
(21) Pyrimidinyloxybenzoic acid herbicidal compound pyrithiobac-sodium, bispyribac-sodium, pyriminobac-methyl, pyribenzoximpy , Pyrimisulfan, triafamon, etc .;
(22) Other strains of herbicidal compounds: bentazone, bromacil, terbacil, chlorthiamid, isoxaben, dinoseb, amitrol, inmethyline, inmethyline Tridiphane, dalapon, diflufenzopyr-sodium, dithiopyr, thiazopyr, sodium flucarbazone, flucarbazone , Mefenacet, flufenacet, fentrazamide, caffentrol, indanophan, oxaziclomefone, benfrate, benfrate Norflurazon, flurtamone, diflufenican, picolinafene, beflubutamid, clomazone, amicarbazone one), pinoxaden, pyraclonil, pyroxasulphone, thiencarbazone-methyl, aminocyclopyrazole (thibenzoen) Fenoxasulfone.

Examples of the active ingredient of such a drug reducing agent include the following.
Benoxacol, cloquintocet-mexyl, ciomethrinil, dichlormid, fenchlorazole (fluzolazole), fenchlorimole (fluchlorzole) Mefenpyr-diethyl, MG191, oxabetrinil, alidochlor, isoxadifen-ethyl, cyprosulfamide, fluoxphenim ), 1,8-naphthalic anhydride (1,8-naphthalic anhydride), AD-67.

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

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, spiromesifen, sulfoxafurol, sulfur, metaflumizone, metaflumizone Mat (spirotetrama) ), Pyrifluquinazon (pyrifluquinazone), 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、Ｃ_１−Ｃ_４ハロアルキル基又はＣ_１−Ｃ_４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Ｃ_１−Ｃ_４アルキル、置換されていてもよいＣ_３−Ｃ_４アルケニル、置換されていてもよいＣ_３−Ｃ_４アルキニル、置換されていてもよいＣ_３−Ｃ_５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)

(In the formula, X ^a1 represents a methyl group, chlorine, bromine or fluorine, X ^a2 represents fluorine, chlorine, bromine, a C ₁ -C ₄ haloalkyl group or a C ₁ -C ₄ haloalkoxy group, and X ^a3 represents fluorine. X ^a4 represents ^optionally substituted C ₁ -C ₄ alkyl, optionally substituted C ₃ -C ₄ alkenyl, optionally substituted C ₃ -C ₄ alkynyl, 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Ｃ_１−Ｃ_４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Ｃ_３−Ｃ_６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Ｃ_１−Ｃ_４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Ｃ_１−Ｃ_４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Ｃ_１−Ｃ_４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 substituted such as a C ₁ -C ₄ alkyl group such as a 3,3,3-trifluoropropyl group or a 2,2,2-trichloroethoxy group) Represents 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 represents 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 Benthiavalicarb, cyazofamid, mandipropamide, metraphenone, fluopiram, bixafen, and the like.

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.

Examples of the control target of the herbicide of the present invention include the following.
Crabgrass (Digitaria ciliaris), goosegrass (Eleusine indica), green foxtail (Setaria viridis), giant foxtail (Setaria faberi), Kin foxtail (Setaria glauca), barnyardgrass (Echinochloa crus-galli), fall panicum (Panicum dichotomiflorum), Texas Pani cam (Panicum texanum), Meriken acne (Brachiaria platyphylla), Alexander glass (Braciaria plantagenea), Surinamegrass (Braciaria decumbens), Sebum sorghum (Sorghum halekeense) Emissions (Andropogon sorghum), bermudagrass (Cynodon dactylon), oats (Avena fatua), darnel (Lolium multiflorum), black grass (Alopecurus myosuroides), downy brome (Bromus tectorum), Arechinochahiki (Bromus sterilis), Hime canary grass (Phalaris minor) , Apera spica-venti, Poa annua, Agropyron repens, Cyperus iria, Cyperus rotundus, cymus , Pollula oleracea, Amaranthus retroflexus, Amaranthus hydritus, Amaranthus palm, Amaranthus palmeri, Anthus amuth spinosa), buckwheat (Fallopia convolvulus), sanaetade (Polygonum scabulum), American scorpiona (Persicaria pennsylvanica), hartade (Persicaria vulgaris), nagapumushi r Shi (Rumex obtusifolius), Japanese knotweed (Fallopia japonica), common lambsquarters (Chenopodium album), kochia (Kochia scoparia), knotweed (Polygonum longisetum), black nightshade (Solanum nigrum), white nosed Datura (Datura stramonium), Ipomoea purpurea (Ipomoea purpurea) , American morning glory (Ipomoea hederacea), Malmo American morning glory (Ipomoea hederacea var. integriuscula), beans morning glory (Ipomoea lacunosa), field bindweed (Convolvulus arvensis), Lamium purpureum (Lamium purpureum), henbit (Lamium amplexicaule), cocklebur (Xanthium pensylvanicum), wild sunflower (Helianthus annuus), Inukamitsure (Matricaria perforata or inodora), Chamomile (Matricaria chamomilla), corn marigold (Chrysanthemum segetum), orrasia (Matricaria matricariaides), ragweed (Ambrosia artemisiifo) ia), Ambrosia trifida (Ambrosia trifida), Erigeron canadensis (Erigeron canadensis), mugwort (Artemisia princeps), goldenrod (Solidago altissima), Erigeron bonariensis (Conyza bonariensis), the United States horn Aeschynomene indica (Sesbania exaltata), sicklepod (Cassia obtusifolia), Florida Bega Weed (Desmodium tortusum), White clover (Trifolium repens), Kudzu (Pueraria lobata), Caladium pea (Vicia angustifolia), Clover (Commelina communis) lina benghalensis), cleavers (Galium aparine), chickweed (Stellaria media), wild radish (Raphanus raphanistrum), Noharagarashi (Sinapis arvensis), shepherd's purse (Capsella bursa-pastoris), persian speedwell (Veronica persica), Veronica Hederifolia (Veronica hederifolia), field Pansy (Viola arvensis), Wild pansy (Viola tricolor), Papaver rhoeas, Forget-me-nots (Myosotis scorpioides), Otoweed (Asclepias syriaca) phorbia helioscopia), Euphorbia nutans (Chamaesyce nutans), the United States Fuuro (Geranium carolinianum), Netherlands Fuuro (Erodium cicutarium), horsetail (Equisetum arvense), Ashikaki (Leersia japonica), barnyardgrass (Echinochloa oryzicola), barnyardgrass (Echinochloa crus-galli var. formosensis), leptochloa chinensis (Leptochloa chinensis), smallflower umbrellaplant (Cyperus difformis), fimbristylis miliacea (Fimbristylis miliacea), Eleocharis acicularis (Eleocharis acicularis), Scirpus (Scirpus juncoides), Taiwan Yamai (Scirpus wallichii), Cyperus (Cyperus serotinus), water chestnut (Eleocharis kuroguwai ), Bobchochoenus koshevnikikovii, Shizunofectus nipponicus, Konogi (Mononochoria vaginalis), Azena (Lindernia procucu) bens), Abunome (Dopatrium junceum), Rotala indica (Rotala indica), Ammannia multiflora Roxb (Ammannia multiflora), Elatine triandra Schk (Elatine triandra), Choujitade (Ludwigia epilobioides), arrowhead (Sagittaria pygmaea), alisma canaliculatum (Alisma canaliculatum), Alismataceae (Sagittaria trifolia) , Potamogeton distinctus, Seri (Oenanthe javanica), Mizuhakobe (Callirichiche palustris), Azeto pepper (Lindernia mitrantha), American azena (Linder) ubia), Eclipta prostrata (Eclipta prostrata), Ibokusa (Murdannia keisak), Paspalum distichum (Paspalum distichum), Ezonosayanukagusa (Leersia oryzoides) weeds such as. Naganetera phyloxeroides, Frogsbit (Limnobium spongia), Waterfern (Salvinia spp.), Duckweed (Pistia stratiotes), Water pennywort (genus Hydrocotyle spp.) demersum), duckweed (genus Lemna), cabbage caroliniana, blackberry (Hydrilla verticillata), Southern naad (Najas guadalupensis), pondweet (Potamogeton) n illinoensis, etc. Potamogeton Pectinatus) Water meal (Wolffia genus), water mills foil such (Myriophyllum spicatum, Myriophyllum heterophyllum etc.), water hyacinth (Eichhornia crassipes) or the like aquatic plants. Mosses, moss, hornworts. Cyanobacteria. Ferns. Suckers of perennial crops (fruits, stones, berries, nuts, citrus, hops, grapes, etc.).

本反応は通常溶媒中で行われる。使用できる溶媒としては、例えば、ジエチルエーテル、ジオキサン、ＴＨＦ、ジメトキシエタン等のエーテル類又はこれらの混合溶媒が挙げられる。
本反応に用いられる塩基としては、例えば、トリエチルアミン、ピリジン等の有機塩基が挙げられる。
本反応に用いられる式（ＩＶ)で示される化合物の使用量は、式（Ｖ）で示される化合物に対して、通常０．５〜１０モル当量、好ましくは１〜３モル当量である。本反応に用いられる塩基の使用量は、式（Ｖ）で示される化合物に対して、通常０．５〜１０モル当量、好ましくは１〜５モル当量である。
本反応の反応温度は通常、−３０〜１８０℃、好ましくは−１０〜８０℃である。本反応の反応時間は通常、１０分〜３０時間である。
本反応では、式（Ｉ）で示される化合物と、式（Ｉ）で示される化合物の異性体である式（Ｅ）で示される化合物も生成する。本反応の終了後は、例えば反応混合物を水と混合し、有機溶媒にて抽出し、得られた有機層を乾燥、濃縮した後、式（Ｉ）で示される化合物と式（Ｅ）で示される化合物との混合物を、シリカゲルカラムクロマトグラフィーに付すことにより、式（Ｉ）で示される化合物を単離することができる。 The compound of the present invention can be produced, for example, by the following production method.
Manufacturing method 1
The compound represented by the formula (I) which is the compound of the present invention can be produced by reacting the compound represented by the formula (V), the compound represented by the formula (IV) and a base.

This reaction is usually performed in a solvent. As a solvent which can be used, ethers, such as diethyl ether, a dioxane, THF, dimethoxyethane, or these mixed solvents are mentioned, for example.
Examples of the base used in this reaction include organic bases such as triethylamine and pyridine.
The usage-amount of the compound shown by Formula (IV) used for this reaction is 0.5-10 molar equivalent normally with respect to the compound shown by Formula (V), Preferably it is 1-3 molar equivalent. The usage-amount of the base used for this reaction is 0.5-10 molar equivalent normally with respect to the compound shown by Formula (V), Preferably it is 1-5 molar equivalent.
The reaction temperature of this reaction is usually −30 to 180 ° C., preferably −10 to 80 ° C. The reaction time for this reaction is usually 10 minutes to 30 hours.
In this reaction, a compound represented by formula (I) and a compound represented by formula (E) which is an isomer of the compound represented by formula (I) are also produced. After completion of this reaction, for example, the reaction mixture is mixed with water and extracted with an organic solvent. The obtained organic layer is dried and concentrated, and then the compound represented by formula (I) and formula (E) are used. The compound represented by the formula (I) can be isolated by subjecting the mixture with the compound to be subjected to silica gel column chromatography.

The compound represented by the formula (IV) is a known compound or can be produced from a known compound.
The compound represented by the formula (V) can be produced according to Reference Production Method 1 shown below.

〔式中、Ｘ¹、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵及びＡは前記と同じ意味を表す。〕
本反応は通常溶媒中で行われる。使用できる溶媒としては、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、ジオキサン、テトラヒドロフラン（以下、ＴＨＦと記す）、ジメトキシエタン等のエーテル類；ジメチルホルムアミド（以下、ＤＭＦと記す）等のアミド類；ジメチルスルホキシド（以下、ＤＭＳＯと記す）等のスルホキシド類；アセトニトリル等のニトリル類；アセトン等のケトン類又はこれらの混合溶媒が挙げられる。
本反応に用いられる塩基としては、例えば、カリウムｔｅｒｔ−ブトキシド等の金属アルコキシド、炭酸カリウム、炭酸セシウム、水素化ナトリウム等の無機塩基が挙げられる。
本反応に用いられる式（ＩＩＩ)で示される化合物の使用量は、式（ＩＩ）で示される化合物に対して、通常０．５〜３モル当量、好ましくは１〜２モル当量である。本反応に用いられる塩基の使用量は、式（ＩＩ）で示される化合物に対して、通常１〜１０モル当量、好ましくは１〜３モル当量である。
本反応の反応温度は通常０〜２００℃、好ましくは２０〜１００℃である。本反応の反応時間は通常１０分〜３０時間である。
本反応の終了後、例えば反応混合物に酸を添加して中和し、水と混合し、有機溶媒にて抽出し、得られた有機層を乾燥、濃縮し、シリカゲルカラムクロマトグラフィーによる精製等の操作を行うことにより、式（Ｖ）で示される化合物を単離することができる。
式（ＩＩ）で示される化合物は、公知の化合物であるか、あるいは公知の化合物から以下の参考製造法２−１に準じて製造することができる。 Reference manufacturing method 1
The compound represented by the formula (V) can be produced from the compound represented by the formula (II).

[Wherein, X ¹ , R ¹ , R ² , R ³ , R ⁴ , R ⁵ and A represent the same meaning as described above. ]
This reaction is usually performed in a solvent. Examples of the solvent that can be used include aromatic hydrocarbons such as benzene, toluene, and xylene; ethers such as diethyl ether, dioxane, tetrahydrofuran (hereinafter referred to as THF), and dimethoxyethane; dimethylformamide (hereinafter referred to as DMF). Amides such as dimethyl sulfoxide (hereinafter referred to as DMSO); nitriles such as acetonitrile; ketones such as acetone or a mixed solvent thereof.
Examples of the base used in this reaction include metal alkoxides such as potassium tert-butoxide, and inorganic bases such as potassium carbonate, cesium carbonate and sodium hydride.
The usage-amount of the compound shown by Formula (III) used for this reaction is 0.5-3 molar equivalent normally with respect to the compound shown by Formula (II), Preferably it is 1-2 molar equivalent. The usage-amount of the base used for this reaction is 1-10 molar equivalent normally with respect to the compound shown by Formula (II), Preferably it is 1-3 molar equivalent.
The reaction temperature of this reaction is usually 0 to 200 ° C, preferably 20 to 100 ° C. The reaction time for this reaction is usually 10 minutes to 30 hours.
After completion of this reaction, for example, the reaction mixture is neutralized by adding acid, mixed with water, extracted with an organic solvent, and the resulting organic layer is dried, concentrated, purified by silica gel column chromatography, etc. By performing the operation, the compound represented by the formula (V) can be isolated.
The compound represented by the formula (II) is a known compound, or can be produced from a known compound according to the following Reference Production Method 2-1.

〔式中、Ｒ^1２はＣ_１−６アルキル基又はベンジル基を表し、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴及びＲ⁵は前記と同じ意味を表す。〕
本反応に用いられる酸としては、例えば、塩酸又は臭化水素酸が挙げられる。本反応に用いられる酸の使用量は、式（ＶＩ）で示される化合物に対して、通常１〜２０モル当量である。
本反応は無溶媒または溶媒中で行われる。使用できる溶媒としては、例えば、酢酸、プロピオン酸等の有機酸、水又はこれらの混合溶媒が挙げられる。
本反応の反応温度は通常、３０〜１８０℃、好ましくは５０〜１３０℃である。本反応の反応時間は通常、１０分〜３０時間である。
本反応の終了後、例えば反応混合物を水と混合し、有機溶媒にて抽出し、得られた有機層を乾燥、濃縮し、シリカゲルカラムクロマトグラフィーによる精製等の操作を行うことにより、式（ＶＩ）で示される化合物を単離することができる。 Reference production method 2-1
The compound represented by the formula (II) can be produced, for example, by reacting the compound represented by the formula (VI) with an acid.

[Wherein R ¹² represents a C _1-6 alkyl group or a benzyl group, and R ¹ , R ² , R ³ , R ⁴ and R ⁵ represent the same meaning as described above. ]
As an acid used for this reaction, hydrochloric acid or hydrobromic acid is mentioned, for example. The usage-amount of the acid used for this reaction is 1-20 molar equivalent normally with respect to the compound shown by Formula (VI).
This reaction is carried out without solvent or in a solvent. Examples of the solvent that can be used include organic acids such as acetic acid and propionic acid, water, and mixed solvents thereof.
The reaction temperature of this reaction is usually 30 to 180 ° C, preferably 50 to 130 ° C. The reaction time for this reaction is usually 10 minutes to 30 hours.
After the completion of this reaction, for example, the reaction mixture is mixed with water and extracted with an organic solvent, and the obtained organic layer is dried, concentrated, and subjected to operations such as purification by silica gel column chromatography. ) Can be isolated.

〔式中、Ｘ^２、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵及びＲ^1２は前記と同じ意味を表す。〕
本反応は通常溶媒中で行われる。使用できる溶媒としては、例えば、ベンゼン、トルエン等の芳香族炭化水素類；メタノール、エタノール、プロパノール等のアルコール類；ジエチルエーテル、ジオキサン、ＴＨＦ、ジメトキシエタン等のエーテル類；アセトン、メチルエチルケトン等のケトン類；ＤＭＦ等のアミド類；ＤＭＳＯ等のスルホキシド類；水又はこれらの混合溶媒が用いられる。
本反応に用いられる塩基としては、例えば、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸セシウム、リン酸カリウム等の無機塩基が挙げられる。用いられる塩基の使用量は、式（ＶＩＩ）で示される化合物に対して、通常１〜１０モル当量、好ましくは１〜５モル当量である。
本反応に用いられる触媒としては、例えば、パラジウム（ＩＩ）アセタート、テトラキス（トリフェニルホスフィン）パラジウム、トリス（ジベンジリデンアセトン）ジパラジウム等のパラジウム触媒等が挙げられる。用いられる触媒の使用量は、式（ＶＩＩ）で示される化合物に対して、通常０．００１〜０．５モル当量、好ましくは０．０１〜０．２モル当量である。
本反応にはまたリガンドを添加することができる。用いられるリガンドとしては、例えば、２−ジシクロヘキシルホスフィノ−２’，６’−ジメトキシビフェニル等が挙げられる。用いられるリガンドの使用量は、式（ＶＩＩ）で示される化合物に対して、通常０．００２〜１モル当量、好ましくは０．０２〜０．４モル当量である。
本反応に用いられる式（ＶＩＩＩ）で示される化合物の使用量は、式（ＶＩＩ）で示される化合物に対して、通常０．５〜２モル当量、好ましくは１〜１．５モル当量である。
本反応の反応温度は通常、０〜１８０℃、好ましくは３０〜１５０℃である。本反応の反応時間は通常、１０分〜１００時間である。
本反応の終了後、例えば反応混合物を水と混合し、有機溶媒にて抽出し、得られた有機層を乾燥、濃縮し、シリカゲルカラムクロマトグラフィーによる精製等の操作を行うことにより、式（ＶＩ）で示される化合物を単離することができる。
式（ＶＩＩＩ）で示される化合物は公知の化合物であるか、あるいは公知の化合物から製造することができる。
式（ＶＩＩ）で示される化合物は、公知の化合物であるか、あるいは公知の化合物から製造することができる。例えばジャーナル・オブ・ヘテロサイクリック・ケミストリー（Ｊ．Ｈｅｔｅｒｏｃｙｃｌ．Ｃｈｅｍ．）、３３巻、１５７９〜１５８２頁（１９９６年）等に記載されている方法、又はそれらに準じる方法に従い製造することができる。 Reference production method 2-2
The compound represented by the formula (VI) can be produced, for example, by reacting the compound represented by the formula (VII) with the compound represented by the formula (VIII) in the presence of a catalyst and a base.

[Wherein, X ² , R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ¹² represent the same meaning as described above. ]
This reaction is usually performed in a solvent. Examples of usable solvents include aromatic hydrocarbons such as benzene and toluene; alcohols such as methanol, ethanol and propanol; ethers such as diethyl ether, dioxane, THF and dimethoxyethane; ketones such as acetone and methyl ethyl ketone. Amides such as DMF; sulfoxides such as DMSO; water or a mixed solvent thereof is used.
As a base used for this reaction, inorganic bases, such as sodium carbonate, potassium carbonate, sodium hydrogencarbonate, cesium carbonate, potassium phosphate, are mentioned, for example. The usage-amount of the base used is 1-10 molar equivalent normally with respect to the compound shown by Formula (VII), Preferably it is 1-5 molar equivalent.
Examples of the catalyst used in this reaction include palladium catalysts such as palladium (II) acetate, tetrakis (triphenylphosphine) palladium, and tris (dibenzylideneacetone) dipalladium. The usage-amount of the catalyst used is 0.001-0.5 molar equivalent normally with respect to the compound shown by Formula (VII), Preferably it is 0.01-0.2 molar equivalent.
A ligand can also be added to this reaction. Examples of the ligand used include 2-dicyclohexylphosphino-2 ′, 6′-dimethoxybiphenyl. The amount of the ligand used is usually 0.002 to 1 molar equivalent, preferably 0.02 to 0.4 molar equivalent, relative to the compound represented by the formula (VII).
The amount of the compound represented by formula (VIII) used in this reaction is usually 0.5 to 2 molar equivalents, preferably 1 to 1.5 molar equivalents, relative to the compound represented by formula (VII). .
The reaction temperature of this reaction is usually 0 to 180 ° C, preferably 30 to 150 ° C. The reaction time of this reaction is usually 10 minutes to 100 hours.
After the completion of this reaction, for example, the reaction mixture is mixed with water and extracted with an organic solvent, and the obtained organic layer is dried, concentrated, and subjected to operations such as purification by silica gel column chromatography. ) Can be isolated.
The compound represented by the formula (VIII) is a known compound or can be produced from a known compound.
The compound represented by the formula (VII) is a known compound or can be produced from a known compound. For example, it can be produced according to the method described in Journal of Heterocyclic Chemistry (J. Heterocycl. Chem.), Vol. 33, pages 1579 to 1582 (1996), or the like.

〔式中、Ｘ^３は、塩素、臭素、ヨウ素、ハロゲンを有していてもよいＣ_1-3アルキルスルホニルオキシ基（例えば、メチルスルホニルオキシ基、トリフルオロメチルスルホニルオキシ基等）、ベンゼンスルホニル基またはｐ−トルエンスルホニル基を表し、Ｒ^1３は、Ｃ_1-6アルキル基、Ｃ_1-6ハロアルキル基、Ｃ_3-8シクロアルキル基、（Ｃ_3-8シクロアルキル）Ｃ_1-6アルキル基、（Ｃ_1-6アルキルチオ）Ｃ_1-6アルキル基、（Ｃ_1-6アルコキシ）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、シアノＣ_1-6アルキル基、（Ｃ_1-6アルコキシ）カルボニルＣ_1-6アルキル基、カルバモイルＣ_1-6アルキル基、｛（Ｃ_1-6アルキル）アミノカルボニル｝Ｃ_1-6アルキル基、または｛ジ（Ｃ_1-6アルキル）アミノカルボニル｝Ｃ_1-6アルキル基を表し、Ｒ¹及びＲ^1２は前記と同じ意味を表す。〕
工程１は式（ＩＸ）で示される化合物と式（Ｘ）で示される化合物とを反応させることにより式（ＸＩ）で示される化合物を製造することができる。本反応は、無水マレイン酸とヒドラジン化合物との脱水縮合反応であり、既知の条件下で反応を行うことができる。例えば、米国特許７８１６３５７に記載の方法に準じて製造することができる。
工程２は式（ＸＩ）で示される化合物と式（ＸＩＩ）で示される化合物とを塩基の存在下で反応させることにより式（ＸＩＩＩ）で示される化合物を製造することができる。本反応は既知の条件下で反応を行うことができる。例えば、国際公開第２０１２／０９１１５６号パンフレット（ＷＯ２０１２／０９１１５６）に記載の方法に準じて製造することができる。
工程３は式（ＸＩＩＩ）で示される化合物と式（ＸＩＶ）で示される化合物とを塩基の存在下で反応させることにより式（ＸＶ）で示される化合物を製造することができる。
本反応は通常溶媒中で行われる。使用できる溶媒としては、例えば、メタノール、エタノール、プロパノール等のアルコール類；ジエチルエーテル、ジオキサン、ＴＨＦ、ジメトキシエタン等のエーテル類；ＤＭＦ等のアミド類；ＤＭＳＯ等のスルホキシド類又はこれらの混合溶媒が用いられる。
本反応に用いられる塩基としては、例えば、ナトリウムメトキシド、カリウムｔｅｒｔ−ブトキシド及び水素化ナトリウム等が挙げられる。本反応に用いられる塩基の使用量は、式（ＸＩＩＩ）で示される化合物に対して、通常０．５〜１０モル当量、好ましくは１〜１．５モル当量である。
本反応の反応温度は通常、−３０〜１００℃である。本反応の反応時間は通常、１０分〜５０時間である。
本反応の終了後、例えば反応混合物を水と混合し、有機溶媒にて抽出し、得られた有機層を乾燥、濃縮等の操作を行うことにより、式（ＸＶ）で示される化合物を単離することができる。 Reference production method 2-3
The compound represented by the formula (XV) in which R ² is O—R ¹³ and X ² is chlorine among the compounds represented by the formula (VII) can be produced, for example, by the following reaction scheme.

[Wherein X ³ represents a C _1-3 alkylsulfonyloxy group (eg, methylsulfonyloxy group, trifluoromethylsulfonyloxy group, etc.), benzenesulfonyl group optionally having chlorine, bromine, iodine, or halogen. Or a p-toluenesulfonyl group, R ¹³ is a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _3-8 cycloalkyl group, a (C _3-8 cycloalkyl) C _1-6 alkyl group, (C _1-6 alkylthio) C _1-6 alkyl group, (C _1-6 alkoxy) C _1-6 alkyl group, C _3-6 alkenyl group, C _3-6 alkynyl group, cyano C _1-6 alkyl group, (C _1-6 alkoxy) carbonyl C _1-6 alkyl group, carbamoyl C _1-6 alkyl group, {(C _1-6 alkyl) aminocarbonyl} C _1-6 alkyl group, or {di (C _1-6 alkyl) ) an amino carbonyl} C _1-6 alkyl group R ¹ and R ¹² are as defined above. ]
In step 1, the compound represented by the formula (XI) can be produced by reacting the compound represented by the formula (IX) with the compound represented by the formula (X). This reaction is a dehydration condensation reaction between maleic anhydride and a hydrazine compound, and can be performed under known conditions. For example, it can be produced according to the method described in US Pat. No. 7,816,357.
In step 2, a compound represented by the formula (XIII) can be produced by reacting a compound represented by the formula (XI) with a compound represented by the formula (XII) in the presence of a base. This reaction can be performed under known conditions. For example, it can be produced according to the method described in International Publication No. 2012/091156 (WO2012 / 091156).
In step 3, the compound represented by the formula (XV) can be produced by reacting the compound represented by the formula (XIII) with the compound represented by the formula (XIV) in the presence of a base.
This reaction is usually performed in a solvent. Examples of the solvent that can be used include alcohols such as methanol, ethanol, and propanol; ethers such as diethyl ether, dioxane, THF, and dimethoxyethane; amides such as DMF; sulfoxides such as DMSO, or a mixed solvent thereof. It is done.
Examples of the base used in this reaction include sodium methoxide, potassium tert-butoxide, sodium hydride and the like. The usage-amount of the base used for this reaction is 0.5-10 molar equivalent normally with respect to the compound shown by Formula (XIII), Preferably it is 1-1.5 molar equivalent.
The reaction temperature of this reaction is usually −30 to 100 ° C. The reaction time of this reaction is usually 10 minutes to 50 hours.
After completion of this reaction, for example, the reaction mixture is mixed with water and extracted with an organic solvent, and the resulting organic layer is dried, concentrated, etc., to isolate the compound represented by the formula (XV). can do.

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, dd: double doublet, m: multiplet, J: coupling constant, THF: tetrahydrofuran.

「本発明化合物Ｉ−１」
¹Ｈ ＮＭＲ（ＣＤＣｌ₃）δ ｐｐｍ：1.05 (9H, s), 1.14 (3H, t, J = 7.7 Hz), 2.37-2.60 (5H, m), 3.76 (3H, s), 6.97 (1H, dd, J = 8.4, 2.4 Hz), 7.05 (1H, d, J = 8.4 Hz), 7.09 (1H, d, J = 2.4 Hz), 7.96 (1H, d, J = 2.3 Hz), 8.17 (1H, d, J=2.3 Hz).
「化合物Ｅ−１」
¹Ｈ ＮＭＲ（ＣＤＣｌ₃）δ ｐｐｍ：1.05 (9H, s), 1.15 (3H, t, J = 7.6 Hz), 2.24 (3H, s), 2.38-2.61 (2H, m), 3.83 (3H, s), 6.99 (1H, dd, J = 8.4, 2.3 Hz), 7.07 (1H, d, J = 8.4 Hz), 7.10 (1H, d, J = 2.3 Hz), 7.97 (1H, d, J = 2.1 Hz), 8.17 (1H, d, J = 2.1 Hz). Production Example 1
4- [4- {3-Chloro-5- (trifluoromethyl) pyridin-2-yloxy} -2-ethylphenyl] -2,6-dimethyl-3-pivaloyloxy-5 (2H) -pyridazinone (the compound of the present invention) Synthesis of I-1)
4- [4- {3-Chloro-5- (trifluoromethyl) pyridin-2-yloxy} -2-ethylphenyl] -2,6-dimethyl-5-hydroxy-3 (2H) -pyridazinone 310 mg and triethylamine 0 To a solution of 3 ml dissolved in 3 ml of THF, 170 mg of pivaloyl chloride was added dropwise at room temperature and stirred for 30 minutes. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure.
The residue was subjected to silica gel column chromatography, and 302 mg of 4- [4- {3-chloro-5- (trifluoromethyl) pyridin-2-yloxy} -2-ethylphenyl] -2,6-dimethyl-5- Pivaloyloxy-3 (2H) -pyridazinone (Compound E-1) and 50 mg of the present compound I-1 were isolated. Compound E-1 eluted first, and compound I-1 eluted later.

“Invention Compound I-1”
¹ H NMR (CDCl ₃ ) δ ppm: 1.05 (9H, s), 1.14 (3H, t, J = 7.7 Hz), 2.37-2.60 (5H, m), 3.76 (3H, s), 6.97 (1H, dd , J = 8.4, 2.4 Hz), 7.05 (1H, d, J = 8.4 Hz), 7.09 (1H, d, J = 2.4 Hz), 7.96 (1H, d, J = 2.3 Hz), 8.17 (1H, d , J = 2.3 Hz).
“Compound E-1”
¹ H NMR (CDCl ₃ ) δ ppm: 1.05 (9H, s), 1.15 (3H, t, J = 7.6 Hz), 2.24 (3H, s), 2.38-2.61 (2H, m), 3.83 (3H, s ), 6.99 (1H, dd, J = 8.4, 2.3 Hz), 7.07 (1H, d, J = 8.4 Hz), 7.10 (1H, d, J = 2.3 Hz), 7.97 (1H, d, J = 2.1 Hz) ), 8.17 (1H, d, J = 2.1 Hz).

According to the above production example, 4- [4- {3-chloro-5- (trifluoromethyl) pyridin-2-yloxy} -2-ethylphenyl] -2,6-dimethyl-5-hydroxy-3 ( Instead of 2H) -pyridazinone, the following compounds I ^{1 to} I ⁵¹ can be produced using the compounds obtained in the following Reference Production Examples.

1) In the formulas (I ¹ ) to (I ⁵¹ ), G is a pivaloyl group, and A is a phenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 2-bromophenyl group, 3-bromophenyl group, 4-bromophenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 2-trifluoro Methylphenyl group, 3-trifluoromethylphenyl group, 4-trifluoromethylphenyl group, 2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 2-trifluoromethoxyphenyl group, 3-trifluoro Methoxyphenyl group, 4-trifluoromethoxyphenyl group, 2-nitrophenyl group, 3-nitropheny Group, 4-nitrophenyl group, 2-cyanophenyl group, 3-cyanophenyl group, 4-cyanophenyl group, 2-fluoro-4-chlorophenyl group, 2-fluoro-4-cyanophenyl group, 2-fluoro- 4-trifluoromethylphenyl group, 2,4-dichlorophenyl group, 2-chloro-4-cyanophenyl group, 2-chloro-4-trifluoromethylphenyl group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl Group, 3-fluoropyridin-2-yl group, 4-fluoropyridin-2-yl group, 5-fluoropyridin-2-yl group, 6-fluoropyridin-2-yl group, 3-chloropyridin-2-yl group Group, 4-chloropyridin-2-yl group, 5-chloropyridin-2-yl group, 6-chloropyridin-2-yl group, 3-trifluoromethylpyridine- -Yl group, 4-trifluoromethylpyridin-2-yl group, 5-trifluoromethylpyridin-2-yl group, 6-trifluoromethylpyridin-2-yl group, 3,5-difluoropyridin-2-yl Group, 3-fluoro-5-chloro-pyridin-2-yl group, 3-fluoro-5-trifluoromethyl-pyridin-2-yl group, 3-chloro-5-fluoropyridin-2-yl group, 3, 5-dichloropyridin-2-yl group, 3-chloro-5-trifluoromethylpyridin-2-yl group, 2-pyrimidinyl group, 5-fluoropyrimidinyl group, 5-chloropyrimidinyl group, 6-chloropyridazine-3- Yl group, 2-quinolinyl group, 6-fluoroquinolin-2-yl group, 7-fluoroquinolin-2-yl group, 6-chloroquinolin-2-yl group, 7-chloro Quinolin-2-yl group, 6-trifluoromethylquinolin-2-yl group, 7-trifluoromethylquinolin-2-yl group, quinoxalin-2-yl group, 6-fluoroquinoxalin-2-yl group, 6- Chloroquinoxalin-2-yl group, 6-trifluoromethylquinoxalin-2-yl group, quinazolin-2-yl group, 6-fluoroquinazolin-2-yl group, 6-chloroquinazolin-2-yl group, 6-tri Fluoromethylquinazolin-2-yl group, benzoxazol-2-yl group, 5-fluorobenzoxazol-2-yl group, 5-chlorobenzoxazol-2-yl group, 5-trifluoromethylbenzoxazol-2-yl Group, 6-fluorobenzoxazol-2-yl group, 6-chlorobenzoxazol-2-yl group, 6-trif Fluoromethylbenzoxazol-2-yl group, benzothiazol-2-yl group, 5-fluorobenzothiazol-2-yl group, 5-chlorobenzothiazol-2-yl group, 5-trifluoromethylbenzothiazol-2 -Yl group, 6-fluorobenzothiazol-2-yl group, 6-chlorobenzothiazol-2-yl group, 6-trifluoromethylbenzothiazol-2-yl group, benzo [1,2,4] triazine-3 -Yl group, 6-fluorobenzo [1,2,4] triazin-3-yl group, 6-chlorobenzo [1,2,4] triazin-3-yl group, 7-fluorobenzo [1,2,4] A pyridazinone compound which is a triazin-3-yl group or a 7-chlorobenzo [1,2,4] triazin-3-yl group.

2) In the formulas (I ¹ ) to (I ⁵¹ ), A is a 4-trifluoromethylphenyl group,
G is acetyl group, trifluoroacetyl group, propionyl group, butyryl group, isobutyryl group, isovaleryl group, 2,2-dimethylbutyryl group, 3,3-dimethylbutyryl group, cyclopropylcarbonyl group, cyclobutylcarbonyl group, A pyridazinone compound which is a cyclopentylcarbonyl group, cyclohexylcarbonyl group, benzoyl group, 2-methylbenzoyl group, 3-methylbenzoyl group, 4-methylbenzoyl group, phenylacetyl group, benzyl group or 2-nitrobenzyl group.

3) In the formulas (I ¹ ) to (I ⁵¹ ), A is a 2-fluoro-4-cyanophenyl group,
G is acetyl group, trifluoroacetyl group, propionyl group, butyryl group, isobutyryl group, isovaleryl group, 2,2-dimethylbutyryl group, 3,3-dimethylbutyryl group, cyclopropylcarbonyl group, cyclobutylcarbonyl group, A pyridazinone compound which is a cyclopentylcarbonyl group, cyclohexylcarbonyl group, benzoyl group, 2-methylbenzoyl group, 3-methylbenzoyl group, 4-methylbenzoyl group, phenylacetyl group, benzyl group or 2-nitrobenzyl group.

4) In the formulas (I ¹ ) to (I ⁵¹ ), A is a 2-chloro-4-trifluoromethylphenyl group,
G is acetyl group, trifluoroacetyl group, propionyl group, butyryl group, isobutyryl group, isovaleryl group, 2,2-dimethylbutyryl group, 3,3-dimethylbutyryl group, cyclopropylcarbonyl group, cyclobutylcarbonyl group, A pyridazinone compound which is a cyclopentylcarbonyl group, cyclohexylcarbonyl group, benzoyl group, 2-methylbenzoyl group, 3-methylbenzoyl group, 4-methylbenzoyl group, phenylacetyl group, benzyl group or 2-nitrobenzyl group.

5) In the formulas (I ¹ ) to (I ⁵¹ ), A is a 5-trifluoromethylpyridin-2-yl group,
G is acetyl group, trifluoroacetyl group, propionyl group, butyryl group, isobutyryl group, isovaleryl group, 2,2-dimethylbutyryl group, 3,3-dimethylbutyryl group, cyclopropylcarbonyl group, cyclobutylcarbonyl group, A pyridazinone compound which is a cyclopentylcarbonyl group, cyclohexylcarbonyl group, benzoyl group, 2-methylbenzoyl group, 3-methylbenzoyl group, 4-methylbenzoyl group, phenylacetyl group, benzyl group or 2-nitrobenzyl group.

6) In the formulas (I ¹ ) to (I ⁵¹ ), A is a 2-fluoro-5-trifluoromethylpyridin-2-yl group,
G is acetyl group, trifluoroacetyl group, propionyl group, butyryl group, isobutyryl group, isovaleryl group, 2,2-dimethylbutyryl group, 3,3-dimethylbutyryl group, cyclopropylcarbonyl group, cyclobutylcarbonyl group, A pyridazinone compound which is a cyclopentylcarbonyl group, cyclohexylcarbonyl group, benzoyl group, 2-methylbenzoyl group, 3-methylbenzoyl group, 4-methylbenzoyl group, phenylacetyl group, benzyl group or 2-nitrobenzyl group.

7) In the formulas (I ¹ ) to (I ⁵¹ ), A is a 2-chloro-5-trifluoromethylpyridin-2-yl group,
G is acetyl group, trifluoroacetyl group, propionyl group, butyryl group, isobutyryl group, isovaleryl group, 2-methylbutyryl group, 3-methylbutyryl group, 2,2-dimethylbutyryl group, 3,3-dimethylbutyryl group, Valeryl group, pentanoyl group, 2-methylpentanoyl group, 2-ethylpentanoyl group, 2-propylpentanoyl group, hexanoyl group, 2-methylhexanoyl group, 2-ethylhexanoyl group, phenylacetyl group, 3- Phenylpropionyl group, methoxyacetyl group, ethoxyacetyl group, propoxyacetyl group, 3-methoxypropionyl group, 3-ethoxypropionyl group, 3-methoxy-2-methylpropionyl group, ethylthioacetyl group, 3- (methylthio) propionyl group , Phenoxyacetyl group, benzyl Oxyacetyl group, cyclopropylcarbonyl group, cyclobutylcarbonyl group, cyclopentylcarbonyl group, cyclohexylcarbonyl group, benzoyl group, 2-fluorobenzoyl group, 3-fluorobenzoyl group, 4-fluorobenzoyl group, 2-chlorobenzoyl group, 3 -Chlorobenzoyl group, 4-chlorobenzoyl group, 2-bromobenzoyl group, 4-bromobenzoyl group, 2-methylbenzoyl group, 3-methylbenzoyl group, 4-methylbenzoyl group, 2-ethylbenzoyl group, 2-methoxy Benzoyl group, 3-methoxybenzoyl group, 4-methoxybenzoyl group, 2-ethoxybenzoyl group, 2-methylthiobenzoyl group, 4-cyanobenzoyl group, 2-nitrobenzoyl group, 4-nitrobenzoyl group, 2- (trifluoro Methyl Benzoyl group, 4- (trifluoromethyl) benzoyl group, 4- (trifluoromethoxy) benzoyl group, 2,6-difluorobenzoyl group, 2,3-dichlorobenzoyl group, 2,4-dichlorobenzoyl group, 2,5 -Dichlorobenzoyl group, 2,6-dichlorobenzoyl group, 3,4-dichlorobenzoyl group, 3,5-dichlorobenzoyl group, 2,6-dimethylbenzoyl group, 2,6-dimethoxybenzoyl group, benzyl group or 2- A pyridazinone compound that is a nitrobenzyl group.

8) In the formulas (I ¹ ) to (I ⁵¹ ), A is a 6-chloroquinoxalin-2-yl group,
G is acetyl group, trifluoroacetyl group, propionyl group, butyryl group, isobutyryl group, isovaleryl group, 2,2-dimethylbutyryl group, 3,3-dimethylbutyryl group, cyclopropylcarbonyl group, cyclobutylcarbonyl group, A pyridazinone compound which is a cyclopentylcarbonyl group, cyclohexylcarbonyl group, benzoyl group, 2-methylbenzoyl group, 3-methylbenzoyl group, 4-methylbenzoyl group, phenylacetyl group, benzyl group or 2-nitrobenzyl group.

9) In the formulas (I ¹ ) to (I ⁵¹ ), A is a 6-chlorobenzoxazol-2-yl group,
G is acetyl group, trifluoroacetyl group, propionyl group, butyryl group, isobutyryl group, isovaleryl group, 2,2-dimethylbutyryl group, 3,3-dimethylbutyryl group, cyclopropylcarbonyl group, cyclobutylcarbonyl group, A pyridazinone compound which is a cyclopentylcarbonyl group, cyclohexylcarbonyl group, benzoyl group, 2-methylbenzoyl group, 3-methylbenzoyl group, 4-methylbenzoyl group, phenylacetyl group, benzyl group or 2-nitrobenzyl group.

10) In the formulas (I ¹ ) to (I ⁵¹ ), A is a benzothiazol-2-yl group,
G is acetyl group, trifluoroacetyl group, propionyl group, butyryl group, isobutyryl group, isovaleryl group, 2,2-dimethylbutyryl group, 3,3-dimethylbutyryl group, cyclopropylcarbonyl group, cyclobutylcarbonyl group, A pyridazinone compound which is a cyclopentylcarbonyl group, cyclohexylcarbonyl group, benzoyl group, 2-methylbenzoyl group, 3-methylbenzoyl group, 4-methylbenzoyl group, phenylacetyl group, benzyl group or 2-nitrobenzyl group.

11) In the formulas (I ¹ ) to (I ⁵¹ ), A is a 6-chlorobenzothiazol-2-yl group,
G is acetyl group, trifluoroacetyl group, propionyl group, butyryl group, isobutyryl group, isovaleryl group, 2,2-dimethylbutyryl group, 3,3-dimethylbutyryl group, cyclopropylcarbonyl group, cyclobutylcarbonyl group, A pyridazinone compound which is a cyclopentylcarbonyl group, cyclohexylcarbonyl group, benzoyl group, 2-methylbenzoyl group, 3-methylbenzoyl group, 4-methylbenzoyl group, phenylacetyl group, benzyl group or 2-nitrobenzyl group.

４−（２−エチル−４−ヒドロキシフェニル）−２，６−ジメチル−５−ヒドロキシ−３（２Ｈ）−ピリダジノン（化合物ＩＩ−１）５００ｍｇ、３，４−ジフルオロベンゾニトリル２９４ｍｇ、炭酸セシウム７５１ｍｇ及びＤＭＦ３ｍｌの混合溶液を７０℃で３０分撹拌した。この反応液を室温まで冷却し、２Ｎ塩酸を加えて酸性にした後、ＭＴＢＥで２回抽出し、合わせた有機層を水、飽和食塩水で順次洗浄し、無水硫酸マグネシウムで乾燥し、減圧下濃縮した。得られた残さをシリカゲルカラムクロマトグラフィーで精製し、化合物２７３ｍｇを得た。
^１Ｈ ＮＭＲ（ＣＤＣｌ_３）δ ｐｐｍ：1.10 (3H, t, J = 7.6 Hz), 2.34 (3H, s), 2.38-2.58 (2H, m), 3.75 (3H, s), 5.77 (1H, br s), 6.95 (1H, dd, J = 8.3, 2.4 Hz), 7.08-7.18 (3H, m), 7.42 (1H, dt, J = 8.5, 1.7 Hz), 7.50 (1H, dd, J = 9.9, 1.7 Hz). Hereinafter, production examples of production intermediates of the compound of the present invention will be described.
Reference production example 1

4- (2-ethyl-4-hydroxyphenyl) -2,6-dimethyl-5-hydroxy-3 (2H) -pyridazinone (Compound II-1) 500 mg, 3,4-difluorobenzonitrile 294 mg, cesium carbonate 751 mg and A mixed solution of 3 ml of DMF was stirred at 70 ° C. for 30 minutes. The reaction solution was cooled to room temperature, acidified with 2N hydrochloric acid, extracted twice with MTBE, and the combined organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and dried under reduced pressure. Concentrated. The obtained residue was purified by silica gel column chromatography to obtain 273 mg of a compound.
¹ H NMR (CDCl ₃ ) δ ppm: 1.10 (3H, t, J = 7.6 Hz), 2.34 (3H, s), 2.38-2.58 (2H, m), 3.75 (3H, s), 5.77 (1H, br s), 6.95 (1H, dd, J = 8.3, 2.4 Hz), 7.08-7.18 (3H, m), 7.42 (1H, dt, J = 8.5, 1.7 Hz), 7.50 (1H, dd, J = 9.9, 1.7 Hz).

３，４−ジフルオロベンゾニトリルに代えて、４−フルオロベンゾトリフルオリドを用い、参考製造例１に準じて行い、４−（２−エチル−４−（４−トリフルオロメチルフェノキシ）フェニル）−２，６−ジメチル−５−ヒドロキシ−３（２Ｈ）−ピリダジノンを得た。
^１Ｈ ＮＭＲ（ＣＤＣｌ_３）δ ｐｐｍ：1.11 (3H, t, J = 7.6 Hz), 2.34 (3H, s), 2.39-2.58 (2H, m), 3.76 (3H, s), 5.46 (1H, br s), 6.96 (1H, dd, J = 8.3, 2.7 Hz), 7.08-7.17 (4H, m), 7.61 (2H, d, J = 8.5 Hz). Reference production example 2

4- (2-ethyl-4- (4-trifluoromethylphenoxy) phenyl) -2 was carried out according to Reference Production Example 1 using 4-fluorobenzotrifluoride instead of 3,4-difluorobenzonitrile. , 6-Dimethyl-5-hydroxy-3 (2H) -pyridazinone was obtained.
¹ H NMR (CDCl ₃ ) δ ppm: 1.11 (3H, t, J = 7.6 Hz), 2.34 (3H, s), 2.39-2.58 (2H, m), 3.76 (3H, s), 5.46 (1H, br s), 6.96 (1H, dd, J = 8.3, 2.7 Hz), 7.08-7.17 (4H, m), 7.61 (2H, d, J = 8.5 Hz).

３，４−ジフルオロベンゾニトリルに代えて、３−クロロ−４−フルオロベンゾトリフルオリドを用い、参考製造例１に準じて行い、４−（２−エチル−４−（２−クロロ−４−トリフルオロメチルフェノキシ）フェニル）−２，６−ジメチル−５−ヒドロキシ−３（２Ｈ）−ピリダジノンを得た。
^１Ｈ ＮＭＲ（ＣＤＣｌ_３）δ ｐｐｍ：1.11 (3H, t, J = 7.6 Hz), 2.34 (3H, s), 2.39-2.59 (2H, m), 3.77 (3H, s), 5.47 (1H, br s), 6.93 (1H, dd, J = 8.5, 2.6 Hz), 7.10 (1H, d, J = 2.6 Hz), 7.12 (1H, d, J = 8.5 Hz), 7.15 (1H, d, J = 8.5 Hz), 7.49 (1H, d, J = 8.5 Hz), 7.76 (1H, s). Reference production example 3

Instead of 3,4-difluorobenzonitrile, 3-chloro-4-fluorobenzotrifluoride was used according to Reference Production Example 1, and 4- (2-ethyl-4- (2-chloro-4-tri Fluoromethylphenoxy) phenyl) -2,6-dimethyl-5-hydroxy-3 (2H) -pyridazinone was obtained.
¹ H NMR (CDCl ₃ ) δ ppm: 1.11 (3H, t, J = 7.6 Hz), 2.34 (3H, s), 2.39-2.59 (2H, m), 3.77 (3H, s), 5.47 (1H, br s), 6.93 (1H, dd, J = 8.5, 2.6 Hz), 7.10 (1H, d, J = 2.6 Hz), 7.12 (1H, d, J = 8.5 Hz), 7.15 (1H, d, J = 8.5 Hz), 7.49 (1H, d, J = 8.5 Hz), 7.76 (1H, s).

３，４−ジフルオロベンゾニトリルに代えて、２−クロロ−５−トリフルオロメチルピリジンを用い、参考製造例１に準じて行い、４−（２−エチル−４−（５−トリフルオロメチルピリジン−２−イルオキシ）フェニル）−２，６−ジメチル−５−ヒドロキシ−３（２Ｈ）−ピリダジノンを得た。
^１Ｈ ＮＭＲ（ＣＤＣｌ_３）δ ｐｐｍ：1.12 (3H, t, J = 7.6 Hz), 2.33 (3H, s), 2.40-2.60 (2H, m), 3.76 (3H, s), 6.42 (1H, br s), 7.05-7.11 (2H, m), 7.17 (1H, d, J = 2.2 Hz), 7.19 (1H, d, J = 8.3 Hz), 7.94 (1H, dd, J = 8.7, 2.6 Hz), 8.38-8.40 (1H, m). Reference production example 4

Instead of 3,4-difluorobenzonitrile, 2-chloro-5-trifluoromethylpyridine was used according to Reference Production Example 1, and 4- (2-ethyl-4- (5-trifluoromethylpyridine- 2-yloxy) phenyl) -2,6-dimethyl-5-hydroxy-3 (2H) -pyridazinone was obtained.
¹ H NMR (CDCl ₃ ) δ ppm: 1.12 (3H, t, J = 7.6 Hz), 2.33 (3H, s), 2.40-2.60 (2H, m), 3.76 (3H, s), 6.42 (1H, br s), 7.05-7.11 (2H, m), 7.17 (1H, d, J = 2.2 Hz), 7.19 (1H, d, J = 8.3 Hz), 7.94 (1H, dd, J = 8.7, 2.6 Hz), 8.38-8.40 (1H, m).

３，４−ジフルオロベンゾニトリルに代えて、２，５−ジクロロ−３−フルオロピリジンを用い、参考製造例１に準じて行い、４−（２−エチル−４−（３−フルオロ−５−クロロピリジン−２−イルオキシ）フェニル）−２，６−ジメチル−５−ヒドロキシ−３（２Ｈ）−ピリダジノンを得た。
^１Ｈ ＮＭＲ（ＣＤＣｌ_３）δ ｐｐｍ：1.12 (3H, t, J = 7.6 Hz), 2.34 (3H, s), 2.40-2.60 (2H, m), 3.76 (3H, s), 5.52 (1H, s), 6.94 (1H, dd, J = 8.3, 2.5 Hz), 7.10 (1H, d, J = 2.5 Hz), 7.18 (1H, d, J = 8.3 Hz), 7.36 (1H, d, J = 2.2 Hz), 8.16 (1H, d, J = 2.2 Hz). Reference production example 5

In place of 3,4-difluorobenzonitrile, 2,5-dichloro-3-fluoropyridine was used according to Reference Production Example 1, and 4- (2-ethyl-4- (3-fluoro-5-chloro) was obtained. Pyridin-2-yloxy) phenyl) -2,6-dimethyl-5-hydroxy-3 (2H) -pyridazinone was obtained.
¹ H NMR (CDCl ₃ ) δ ppm: 1.12 (3H, t, J = 7.6 Hz), 2.34 (3H, s), 2.40-2.60 (2H, m), 3.76 (3H, s), 5.52 (1H, s ), 6.94 (1H, dd, J = 8.3, 2.5 Hz), 7.10 (1H, d, J = 2.5 Hz), 7.18 (1H, d, J = 8.3 Hz), 7.36 (1H, d, J = 2.2 Hz) ), 8.16 (1H, d, J = 2.2 Hz).

３，４−ジフルオロベンゾニトリルに代えて、２，３−ジフルオロ−５−トリフルオロメチルピリジンを用い、参考製造例１に準じて行い、４−（２−エチル−４−（３−フルオロ−５−トリフルオロメチルピリジン−２−イルオキシ）フェニル）−２，６−ジメチル−５−ヒドロキシ−３（２Ｈ）−ピリダジノンを得た。
^１Ｈ ＮＭＲ（ＣＤＣｌ_３）δ ｐｐｍ：1.14 (3H, t, J = 7.5 Hz), 2.34 (3H, s), 2.40-2.65 (2H, m), 3.76 (3H, s), 6.38 (1H, br s), 7.12 (1H, dd, J = 8.2, 2.4 Hz), 7.19-7.24 (2H, m), 7.72 (1H, dd, J = 9.3, 1.8 Hz), 8.14 (1H, d, J = 1.8 Hz). Reference production example 6

Instead of 3,4-difluorobenzonitrile, 2,3-difluoro-5-trifluoromethylpyridine was used according to Reference Production Example 1, and 4- (2-ethyl-4- (3-fluoro-5 -Trifluoromethylpyridin-2-yloxy) phenyl) -2,6-dimethyl-5-hydroxy-3 (2H) -pyridazinone was obtained.
¹ H NMR (CDCl ₃ ) δ ppm: 1.14 (3H, t, J = 7.5 Hz), 2.34 (3H, s), 2.40-2.65 (2H, m), 3.76 (3H, s), 6.38 (1H, br s), 7.12 (1H, dd, J = 8.2, 2.4 Hz), 7.19-7.24 (2H, m), 7.72 (1H, dd, J = 9.3, 1.8 Hz), 8.14 (1H, d, J = 1.8 Hz ).

３，４−ジフルオロベンゾニトリルに代えて、２，３−ジクロロ−５−トリフルオロメチルピリジンを用い、参考製造例１に準じて行い、４−（２−エチル−４−（３−クロロ−５−トリフルオロメチルピリジン−２−イルオキシ）フェニル）−２，６−ジメチル−５−ヒドロキシ−３（２Ｈ）−ピリダジノン（本製造中間体Ｖ−１）を得た。
^１Ｈ ＮＭＲ（ＣＤＣｌ_３）δ ｐｐｍ：1.14 (3H, t, J = 7.6 Hz), 2.34 (3H, s), 2.42-2.62 (2H, m), 3.77 (3H, s), 6.43 (1H, br s), 7.11 (1H, dd, J = 8.2, 2.5 Hz), 7.20 (1H, d, J = 2.5 Hz), 7.23 (1H, d, J = 8.2 Hz), 8.02 (1H, d, J = 2.1 Hz), 8.23 (1H, d, J = 2.1 Hz). Reference production example 7

Instead of 3,4-difluorobenzonitrile, 2,3-dichloro-5-trifluoromethylpyridine was used according to Reference Production Example 1, and 4- (2-ethyl-4- (3-chloro-5 -Trifluoromethylpyridin-2-yloxy) phenyl) -2,6-dimethyl-5-hydroxy-3 (2H) -pyridazinone (this production intermediate V-1) was obtained.
¹ H NMR (CDCl ₃ ) δ ppm: 1.14 (3H, t, J = 7.6 Hz), 2.34 (3H, s), 2.42-2.62 (2H, m), 3.77 (3H, s), 6.43 (1H, br s), 7.11 (1H, dd, J = 8.2, 2.5 Hz), 7.20 (1H, d, J = 2.5 Hz), 7.23 (1H, d, J = 8.2 Hz), 8.02 (1H, d, J = 2.1 Hz), 8.23 (1H, d, J = 2.1 Hz).

３，４−ジフルオロベンゾニトリルに代えて、２，６−ジクロロキノキサリンを用い、参考製造例１に準じて行い、４−（２−エチル−４−（６−クロロキノキサリン−２−イルオキシ）フェニル）−２，６−ジメチル−５−ヒドロキシ−３（２Ｈ）−ピリダジノンを得た。
^１Ｈ ＮＭＲ（ＣＤＣｌ_３）δ ｐｐｍ：1.14 (3H, t, J = 7.6 Hz), 2.36 (3H, s), 2.43-2.64 (2H, m), 3.78 (3H, s), 7.00 (1H, br s), 7.19 (1H, dd, J = 8.3, 2.3 Hz), 7.23-7.27 (2H, m), 7.61 (1H, dd, J = 8.9, 2.3 Hz), 7.66 (1H, d, J = 8.9 Hz), 8.07 (1H, d, J = 2.3 Hz), 8.73 (1H, s). Reference production example 8

Instead of 3,4-difluorobenzonitrile, 2,6-dichloroquinoxaline was used according to Reference Production Example 1, and 4- (2-ethyl-4- (6-chloroquinoxalin-2-yloxy) phenyl) -2,6-Dimethyl-5-hydroxy-3 (2H) -pyridazinone was obtained.
¹ H NMR (CDCl ₃ ) δ ppm: 1.14 (3H, t, J = 7.6 Hz), 2.36 (3H, s), 2.43-2.64 (2H, m), 3.78 (3H, s), 7.00 (1H, br s), 7.19 (1H, dd, J = 8.3, 2.3 Hz), 7.23-7.27 (2H, m), 7.61 (1H, dd, J = 8.9, 2.3 Hz), 7.66 (1H, d, J = 8.9 Hz ), 8.07 (1H, d, J = 2.3 Hz), 8.73 (1H, s).

３，４−ジフルオロベンゾニトリルに代えて、２，６−ジクロロベンズオキサゾールを用い、参考製造例１に準じて行い、４−（２−エチル−４−（６−クロロベンズオキサゾール−２−イルオキシ）フェニル）−２，６−ジメチル−５−ヒドロキシ−３（２Ｈ）−ピリダジノンを得た。
^１Ｈ ＮＭＲ（ＣＤＣｌ_３）δ ｐｐｍ：1.16 (3H, t, J = 7.5 Hz), 2.34 (3H, s), 2.44-2.63 (2H, m), 3.76 (3H, s), 6.27 (1H, br s), 7.24-7.29 (2H, m), 7.35-7.39 (2H, m), 7.41 (1H, d, J = 2.4 Hz), 7.48 (1H, d, J = 1.9 Hz). Reference production example 9

Instead of 3,4-difluorobenzonitrile, 2,6-dichlorobenzoxazole was used according to Reference Production Example 1, and 4- (2-ethyl-4- (6-chlorobenzoxazol-2-yloxy) Phenyl) -2,6-dimethyl-5-hydroxy-3 (2H) -pyridazinone was obtained.
¹ H NMR (CDCl ₃ ) δ ppm: 1.16 (3H, t, J = 7.5 Hz), 2.34 (3H, s), 2.44-2.63 (2H, m), 3.76 (3H, s), 6.27 (1H, br s), 7.24-7.29 (2H, m), 7.35-7.39 (2H, m), 7.41 (1H, d, J = 2.4 Hz), 7.48 (1H, d, J = 1.9 Hz).

３，４−ジフルオロベンゾニトリルに代えて、２−クロロベンゾチアゾールを用い、参考製造例１に準じて行い、４−（２−エチル−４−（ベンゾチアゾール−２−イルオキシ）フェニル）−２，６−ジメチル−５−ヒドロキシ−３（２Ｈ）−ピリダジノンを得た。
^１Ｈ ＮＭＲ（ＣＤＣｌ_３）δ ｐｐｍ：1.15 (3H, t, J = 7.5 Hz), 2.35 (3H, s), 2.43-2.63 (2H, m), 3.77 (3H, s), 6.15 (1H, br s), 7.23 (1H, d, J = 8.5 Hz), 7.28-7.34 (2H, m), 7.37-7.43 (2H, m), 7.68 (1H, d, J = 8.0 Hz), 7.71 (1H, d, J = 8.0 Hz). Reference production example 10

Instead of 3,4-difluorobenzonitrile, 2-chlorobenzothiazole was used according to Reference Production Example 1, and 4- (2-ethyl-4- (benzothiazol-2-yloxy) phenyl) -2, 6-dimethyl-5-hydroxy-3 (2H) -pyridazinone was obtained.
¹ H NMR (CDCl ₃ ) δ ppm: 1.15 (3H, t, J = 7.5 Hz), 2.35 (3H, s), 2.43-2.63 (2H, m), 3.77 (3H, s), 6.15 (1H, br s), 7.23 (1H, d, J = 8.5 Hz), 7.28-7.34 (2H, m), 7.37-7.43 (2H, m), 7.68 (1H, d, J = 8.0 Hz), 7.71 (1H, d , J = 8.0 Hz).

３，４−ジフルオロベンゾニトリルに代えて、２，６−ジクロロベンゾチアゾールを用い、参考製造例１に準じて行い、４−（２−エチル−４−（６−クロロベンゾチアゾール−２−イルオキシ）フェニル）−２，６−ジメチル−５−ヒドロキシ−３（２Ｈ）−ピリダジノンを得た。
^１Ｈ ＮＭＲ（ＣＤＣｌ_３）δ ｐｐｍ：1.15 (3H, t, J = 7.6 Hz), 2.34 (3H, s), 2.42-2.62 (2H, m), 3.76 (3H, s), 6.04 (1H, br s), 7.23 (1H, d, J = 8.5 Hz), 7.32 (1H, dd, J = 8.5, 2.4 Hz), 7.34-7.38 (2H, m), 7.59 (1H, d, J = 8.7 Hz), 7.68 (1H, d, J = 1.9 Hz). Reference production example 11

Instead of 3,4-difluorobenzonitrile, 2,6-dichlorobenzothiazole was used according to Reference Production Example 1, and 4- (2-ethyl-4- (6-chlorobenzothiazol-2-yloxy) Phenyl) -2,6-dimethyl-5-hydroxy-3 (2H) -pyridazinone was obtained.
¹ H NMR (CDCl ₃ ) δ ppm: 1.15 (3H, t, J = 7.6 Hz), 2.34 (3H, s), 2.42-2.62 (2H, m), 3.76 (3H, s), 6.04 (1H, br s), 7.23 (1H, d, J = 8.5 Hz), 7.32 (1H, dd, J = 8.5, 2.4 Hz), 7.34-7.38 (2H, m), 7.59 (1H, d, J = 8.7 Hz), 7.68 (1H, d, J = 1.9 Hz).

化合物ＩＩ−１に代えて、４−（２−メチル−４−ヒドロキシフェニル）−２，６−ジメチル−５−ヒドロキシ−３（２Ｈ）−ピリダジノンを用い、参考製造例７に準じて行い、４−（２−メチル−４−（３−クロロ−５−トリフルオロメチルピリジン−２−イルオキシ）フェニル）−２，６−ジメチル−５−ヒドロキシ−３（２Ｈ）−ピリダジノンを得た。
^１Ｈ ＮＭＲ（ＣＤＣｌ_３）δ ｐｐｍ：2.22 (3H, s), 2.34 (3H, s), 3.77 (3H, s), 6.11 (1H, s), 7.11 (1H, dd, J = 8.5, 2.4 Hz), 7.17 (1H, d, J = 2.4 Hz), 7.25 (1H, d, J = 8.5 Hz), 8.01 (1H, d, J = 2.2 Hz), 8.25 (1H, d, J = 2.2 Hz). Reference production example 12

This was carried out according to Reference Production Example 7 using 4- (2-methyl-4-hydroxyphenyl) -2,6-dimethyl-5-hydroxy-3 (2H) -pyridazinone instead of compound II-1. -(2-Methyl-4- (3-chloro-5-trifluoromethylpyridin-2-yloxy) phenyl) -2,6-dimethyl-5-hydroxy-3 (2H) -pyridazinone was obtained.
¹ H NMR (CDCl ₃ ) δ ppm: 2.22 (3H, s), 2.34 (3H, s), 3.77 (3H, s), 6.11 (1H, s), 7.11 (1H, dd, J = 8.5, 2.4 Hz ), 7.17 (1H, d, J = 2.4 Hz), 7.25 (1H, d, J = 8.5 Hz), 8.01 (1H, d, J = 2.2 Hz), 8.25 (1H, d, J = 2.2 Hz).

化合物ＩＩ−１に代えて、４−（２−エチル−４−ヒドロキシフェニル）−２−メチル−６−メトキシ−５−ヒドロキシ−３（２Ｈ）−ピリダジノンを用い、参考製造例７に準じて行い、４−（２−エチル−４−（３−クロロ−５−トリフルオロメチルピリジン−２−イルオキシ）フェニル）−２−メチル−６−メトキシ−５−ヒドロキシ−３（２Ｈ）−ピリダジノンを得た。
^１Ｈ ＮＭＲ（ＣＤＣｌ_３）δ ｐｐｍ：1.14 (3H, t, J = 7.5 Hz), 2.44-2.62 (2H, m), 3.69 (3H, s), 3.99 (3H, s), 6.36 (1H, br s), 7.07 (1H, dd, J = 8.5, 2.4 Hz), 7.16 (1H, d, J = 2.4 Hz), 7.21 (1H, d, J = 8.5 Hz), 7.98 (1H, d, J = 2.1 Hz), 8.25 (1H, d, J = 2.1 Hz). Reference production example 13

The same procedure as in Reference Production Example 7 was carried out using 4- (2-ethyl-4-hydroxyphenyl) -2-methyl-6-methoxy-5-hydroxy-3 (2H) -pyridazinone instead of compound II-1. 4- (2-ethyl-4- (3-chloro-5-trifluoromethylpyridin-2-yloxy) phenyl) -2-methyl-6-methoxy-5-hydroxy-3 (2H) -pyridazinone was obtained. .
¹ H NMR (CDCl ₃ ) δ ppm: 1.14 (3H, t, J = 7.5 Hz), 2.44-2.62 (2H, m), 3.69 (3H, s), 3.99 (3H, s), 6.36 (1H, br s), 7.07 (1H, dd, J = 8.5, 2.4 Hz), 7.16 (1H, d, J = 2.4 Hz), 7.21 (1H, d, J = 8.5 Hz), 7.98 (1H, d, J = 2.1 Hz), 8.25 (1H, d, J = 2.1 Hz).

参考例１−１
４−ブロモ−３−エチルフェノールの合成

３−エチルフェノール２５．２ｇをクロロホルム３００ｍｌに溶解した溶液にピリジニウムブロミドパーブロミド６９．２７ｇを加え、室温で３０分撹拌した。この反応液を水洗（２回）し、飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥し、減圧下濃縮した。残さをシリカゲルカラムクロマトグラフィー（ヘキサン：酢酸エチル＝９５：５）で精製し、４−ブロモ−３−エチルフェノール３９．１ｇをオイルとして得た。
^１Ｈ ＮＭＲ（ＣＤＣｌ_３）δ ｐｐｍ：1.21 (3H, t, J = 7.6 Hz), 2.69 (2H, q, J = 7.6 Hz), 4.80 (1H, s), 6.55 (1H, dd, J = 8.7, 3.1 Hz), 6.73 (1H, d, J = 3.1 Hz), 7.35 (1H, d, J = 8.7 Hz). Next, Production Examples of the compound represented by the formula (II) are shown in Reference Examples 1 to 3.
Reference Example 1 Synthesis of Compound (II-1)

Reference Example 1-1
Synthesis of 4-bromo-3-ethylphenol

69.27 g of pyridinium bromide perbromide was added to a solution of 25.2 g of 3-ethylphenol in 300 ml of chloroform, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was washed with water (twice), washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 95: 5) to obtain 39.1 g of 4-bromo-3-ethylphenol as an oil.
¹ H NMR (CDCl ₃ ) δ ppm: 1.21 (3H, t, J = 7.6 Hz), 2.69 (2H, q, J = 7.6 Hz), 4.80 (1H, s), 6.55 (1H, dd, J = 8.7 , 3.1 Hz), 6.73 (1H, d, J = 3.1 Hz), 7.35 (1H, d, J = 8.7 Hz).

４−ブロモ−３−エチルフェノール３９．１ｇ（１９４ｍｍｏｌ）、ベンジルブロミド３３．２ｇ（１９４ｍｍｏｌ）、炭酸カリウム２９．６ｇ（２１４ｍｍｏｌ）及びアセトニトリル１２０ｍｌの混合溶液を加熱還流下４時間撹拌した。この反応液を室温まで冷却した後、ろ過し、ろ液を減圧下濃縮した。残さをシリカゲルカラムクロマトグラフィー（ヘキサン：酢酸エチル＝９５：５）で精製し、４−ベンジルオキシ−２−エチルブロモベンゼン４６．２ｇをオイルとして得た。
^１Ｈ ＮＭＲ（ＣＤＣｌ_３）δ ｐｐｍ：1.21 (3H, t, J = 7.6 Hz), 2.71 (2H, q, J = 7.6 Hz), 5.03 (2H, s), 6.68 (1H, dd, J = 8.7, 3.1 Hz), 6.87 (1H, d, J = 3.1 Hz), 7.30-7.45 (6H, m). Reference Example 1-2
Synthesis of 4-benzyloxy-2-ethylbromobenzene

A mixed solution of 39.1 g (194 mmol) of 4-bromo-3-ethylphenol, 33.2 g (194 mmol) of benzyl bromide, 29.6 g (214 mmol) of potassium carbonate and 120 ml of acetonitrile was stirred with heating under reflux for 4 hours. The reaction solution was cooled to room temperature and then filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 95: 5) to obtain 46.2 g of 4-benzyloxy-2-ethylbromobenzene as an oil.
¹ H NMR (CDCl ₃ ) δ ppm: 1.21 (3H, t, J = 7.6 Hz), 2.71 (2H, q, J = 7.6 Hz), 5.03 (2H, s), 6.68 (1H, dd, J = 8.7 , 3.1 Hz), 6.87 (1H, d, J = 3.1 Hz), 7.30-7.45 (6H, m).

４−ベンジルオキシ−２−エチルブロモベンゼン４６．２ｇを無水ＴＨＦ１８０ｍｌに溶解した溶液を−７０℃に冷却し、ブチルリチウム（１．６４ｍｏｌ／Ｌ，ヘキサン溶液）１０６ｍｌをゆっくり滴下した。滴下終了後−５０〜−６０℃で３時間撹拌した後、ホウ酸トリメチル３５ｍｌをゆっくり滴下した。この反応液を−７８℃で３時間撹拌した後、室温にし、さらに一晩撹拌した。この反応液に４規定塩酸１３６ｍｌを加え、２時間撹拌した。この反応液をＭＴＢＥで２回抽出し、飽和食塩水で洗浄し無水硫酸マグネシウムで乾燥し、減圧下濃縮した。残さをシリカゲルカラムクロマトグラフィーで精製し、４−ベンジルオキシ−２−エチルフェニルボロン酸３．８３ｇを固体として得た。
^１Ｈ ＮＭＲ（ＣＤＣｌ_３）δ ｐｐｍ：1.34 (3H, t, J = 7.5 Hz), 3.20 (3H, q, J = 7.5 Hz), 5.14 (2H, s), 6.89-6.96 (2H, m), 7.31-7.50 (5H, m), 8.18 (1H, d, J = 8.2 Hz). Reference Example 1-3
Synthesis of 4-benzyloxy-2-ethylphenylboronic acid

A solution prepared by dissolving 46.2 g of 4-benzyloxy-2-ethylbromobenzene in 180 ml of anhydrous THF was cooled to −70 ° C., and 106 ml of butyl lithium (1.64 mol / L, hexane solution) was slowly added dropwise. After completion of dropping, the mixture was stirred at −50 to −60 ° C. for 3 hours, and 35 ml of trimethyl borate was slowly added dropwise. The reaction was stirred at −78 ° C. for 3 hours, then brought to room temperature and further stirred overnight. To this reaction solution, 136 ml of 4N hydrochloric acid was added and stirred for 2 hours. This reaction solution was extracted twice with MTBE, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 3.83 g of 4-benzyloxy-2-ethylphenylboronic acid as a solid.
¹ H NMR (CDCl ₃ ) δ ppm: 1.34 (3H, t, J = 7.5 Hz), 3.20 (3H, q, J = 7.5 Hz), 5.14 (2H, s), 6.89-6.96 (2H, m), 7.31-7.50 (5H, m), 8.18 (1H, d, J = 8.2 Hz).

４−ブロモ−５−メトキシ−２，６−ジメチル−３（２Ｈ）−ピリダジノン４．８１ｇ、４−ベンジルオキシ−２−エチルフェニルボロン酸５．８２ｇ、テトラキス（トリフェニルホスフィン）パラジウム９５５ｍｇ、炭酸ナトリウム４．８１ｇ、臭化テトラブチルアンモニウム１．６６ｇ、１，４−ジオキサン１７０ｍＬ及び水５０ｍＬの混合物を、窒素雰囲気下、加熱還流下で５時間攪拌した。この反応物を室温まで冷却した後、ＭＴＢＥで２回抽出し、飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥し、減圧下濃縮した。残さをシリカゲルカラムクロマトグラフィー（ヘキサン：酢酸エチル＝２：１）で精製し、４−（２−エチル−４−ベンジルオキシフェニル）−２，６−ジメチル−５−メトキシ−３（２Ｈ）−ピリダジノン６．９１ｇをオイルとして得た。
^１Ｈ ＮＭＲ（ＣＤＣｌ_３）δ ｐｐｍ：1.16 (3H, t, J = 7.6 Hz), 2.27 (3H, s), 2.37-2.59 (2H, m), 3.37 (3H, s), 3.73 (3H, s), 5.08 (2H, s), 6.85 (1H, dd, J = 8.5, 2.6 Hz), 6.96 (1H, d, J = 2.6 Hz), 7.08 (1H, d, J = 8.5 Hz), 7.33 (1H, t, J = 7.3 Hz), 7.40 (2H, t, J = 7.3 Hz), 7.45 (2H, d, J = 7.3 Hz). Reference Example 1-4
Synthesis of 4- (2-ethyl-4-benzyloxyphenyl) -2,6-dimethyl-5-methoxy-3 (2H) -pyridazinone

4-Bromo-5-methoxy-2,6-dimethyl-3 (2H) -pyridazinone 4.81 g, 4-benzyloxy-2-ethylphenylboronic acid 5.82 g, tetrakis (triphenylphosphine) palladium 955 mg, sodium carbonate A mixture of 4.81 g, 1.66 g of tetrabutylammonium bromide, 170 mL of 1,4-dioxane and 50 mL of water was stirred for 5 hours under heating and refluxing in a nitrogen atmosphere. The reaction was cooled to room temperature, extracted twice with MTBE, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 2: 1) to give 4- (2-ethyl-4-benzyloxyphenyl) -2,6-dimethyl-5-methoxy-3 (2H) -pyridazinone. 6.91 g was obtained as an oil.
¹ H NMR (CDCl ₃ ) δ ppm: 1.16 (3H, t, J = 7.6 Hz), 2.27 (3H, s), 2.37-2.59 (2H, m), 3.37 (3H, s), 3.73 (3H, s ), 5.08 (2H, s), 6.85 (1H, dd, J = 8.5, 2.6 Hz), 6.96 (1H, d, J = 2.6 Hz), 7.08 (1H, d, J = 8.5 Hz), 7.33 (1H , t, J = 7.3 Hz), 7.40 (2H, t, J = 7.3 Hz), 7.45 (2H, d, J = 7.3 Hz).

Reference Example 1-5
Synthesis of Compound II-1 4- (2-Ethyl-4-benzyloxyphenyl) -2,6-dimethyl-5-methoxy-3 (2H) -pyridazinone in a solution of 7.45 g in acetic acid 40 ml was dissolved in 47% 23 ml of hydrobromic acid was added and stirred at 100 ° C. for 3 hours. The reaction mixture was poured into ice water, extracted twice with ethyl acetate, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained solid was washed with hexane to obtain 5.03 g of Compound II-1.
¹ H NMR (DMSO-d ₆ ) δ ppm: 0.99 (3H, t, J = 7.6 Hz), 2.20 (3H, s), 2.26 (2H, q, J = 7.6 Hz), 3.55 (3H, s), 6.61 (1H, dd, J = 8.3, 2.5 Hz), 6.70 (1H, d, J = 2.5 Hz), 6.79 (1H, d, J = 8.3 Hz), 9.36 (1H, br s), 9.82 (1H, s).

参考例２−１
４−（２−メチル−４−ベンジルオキシフェニル）−２，６−ジメチル−５−メトキシ−３（２Ｈ）−ピリダジノンの合成

４−ベンジルオキシ−２−エチルフェニルボロン酸に代えて、４−ベンジルオキシ−２−メチルフェニルボロン酸を用い、参考例１−４に準じて４−（２−メチル−４−ベンジルオキシフェニル）−２，６−ジメチル−５−メトキシ−３（２Ｈ）−ピリダジノンを得た。
^１Ｈ ＮＭＲ（ＣＤＣｌ_３）δ ｐｐｍ：2.18 (3H, s), 2.27 (3H, s), 3.36 (3H, s), 3.73 (3H, s), 5.07 (2H, s), 6.85 (1H, dd, J = 8.5, 2.7 Hz), 6.90 (1H, d, J = 2.7 Hz), 7.10 (1H, d, J = 8.5 Hz), 7.30-7.46 (5H, m).
参考例２−２
化合物ＩＩ−２の合成
４−（２−エチル−４−ベンジルオキシフェニル）−２，６−ジメチル−５−メトキシ−３（２Ｈ）−ピリダジノンに代えて、４−（２−メチル−４−ベンジルオキシフェニル）−２，６−ジメチル−５−メトキシ−３（２Ｈ）−ピリダジノンを用い、参考例１−５に準じて行い、化合物ＩＩ−２を得た。
^１Ｈ ＮＭＲ（ＤＭＳＯ−ｄ_６）δ ｐｐｍ：1.96 (3H, s), 2.20 (3H, s), 3.55 (3H, s), 6.60 (1H, dd, J = 8.4, 2.3 Hz), 6.67 (1H, d, J = 2.3 Hz), 6.84 (1H, d, J = 8.4 Hz), 9.35 (1H, s), 9.84 (1H, s). Reference example 2
Synthesis of Compound II-2

Reference Example 2-1
Synthesis of 4- (2-methyl-4-benzyloxyphenyl) -2,6-dimethyl-5-methoxy-3 (2H) -pyridazinone

Instead of 4-benzyloxy-2-ethylphenylboronic acid, 4-benzyloxy-2-methylphenylboronic acid was used and 4- (2-methyl-4-benzyloxyphenyl) was used according to Reference Example 1-4. -2,6-Dimethyl-5-methoxy-3 (2H) -pyridazinone was obtained.
¹ H NMR (CDCl ₃ ) δ ppm: 2.18 (3H, s), 2.27 (3H, s), 3.36 (3H, s), 3.73 (3H, s), 5.07 (2H, s), 6.85 (1H, dd , J = 8.5, 2.7 Hz), 6.90 (1H, d, J = 2.7 Hz), 7.10 (1H, d, J = 8.5 Hz), 7.30-7.46 (5H, m).
Reference Example 2-2
Synthesis of Compound II-2 4- (2-Methyl-4-benzyl) instead of 4- (2-ethyl-4-benzyloxyphenyl) -2,6-dimethyl-5-methoxy-3 (2H) -pyridazinone Oxyphenyl) -2,6-dimethyl-5-methoxy-3 (2H) -pyridazinone was used according to Reference Example 1-5 to give compound II-2.
¹ H NMR (DMSO-d ₆ ) δ ppm: 1.96 (3H, s), 2.20 (3H, s), 3.55 (3H, s), 6.60 (1H, dd, J = 8.4, 2.3 Hz), 6.67 (1H , d, J = 2.3 Hz), 6.84 (1H, d, J = 8.4 Hz), 9.35 (1H, s), 9.84 (1H, s).

参考例３−１
４，５−ジクロロ−６−ヒドロキシ−２−メチル−３（２Ｈ）−ピリダジノンの合成

ジクロロマロン酸無水物１０７ｇをＴＨＦ２００ｍｌに溶解した溶液に、氷冷下メチルヒドラジン２９．５ｇをゆっくり滴下した。この反応液を加熱還流下２時間撹拌した後、減圧下濃縮した。得られた固体をＭＴＢＥ及びアセトンで洗浄し、４，５−ジクロロ−６−ヒドロキシ−２−メチル−３（２Ｈ）−ピリダジノン１００ｇを得た。
^１Ｈ ＮＭＲ（ＤＭＳＯ−ｄ_６）δ ｐｐｍ：3.54 (3H, s), 12.37 (1H, br s).
参考例３−２
４，５−ジクロロ−６−メトキシ−２−メチル−３（２Ｈ）−ピリダジノンの合成

硫酸ジメチル２２．４ｇ、炭酸セシウム３６．８ｇ及びＤＭＦ１００ｍｌの混合物に、７０℃で４，５−ジクロロ−６−ヒドロキシ−２−メチル−３（２Ｈ）−ピリダジノン２０ｇをゆっくり加え、３０分撹拌した。この反応液を氷水に注ぎ、得られた固体をろ過し、固体を水、ＭＴＢＥで順次洗浄し、乾燥して４，５−ジクロロ−６−メトキシ−２−メチル−３（２Ｈ）−ピリダジノン１５．１ｇを得た。
^１Ｈ ＮＭＲ（ＣＤＣｌ_３）δ ｐｐｍ：3.72 (3H, s), 3.92 (3H, s).
参考例３−３
４−クロロ−５，６−ジメトキシ−２−メチル−３（２Ｈ）−ピリダジノンの合成

４，５−ジクロロ−６−メトキシ−２−メチル−３（２Ｈ）−ピリダジノン２．０ｇ（９．５６ｍｍｏｌ）及びメタノール２０ｍｌの混合物に室温で２８％ナトリウムメトキシドメタノール溶液１．９３ｇを加え、３時間撹拌した。この反応液を減圧下濃縮した。得られた固体を水洗し、ヘキサン：ＭＴＢＥ＝３：１の混合溶媒で洗浄し、乾燥して４−クロロ−５，６−ジメトキシ−２−メチル−３（２Ｈ）−ピリダジノン１．２２ｇを得た。
^１Ｈ ＮＭＲ（ＣＤＣｌ_３）δ ｐｐｍ：3.68 (3H, s), 3.90 (3H, s), 4.06 (3H, s).
参考例３−４
４−（２−エチル−４−ベンジルオキシフェニル）−２−メチル−５，６−ジメトキシ−３（２Ｈ）−ピリダジノンの合成

４−クロロ−５，６−ジメトキシ−２−メチル−３（２Ｈ）−ピリダジノン１．０３ｇ、４−ベンジルオキシ−２−エチルフェニルボロン酸１．４２ｇ、２−ジシクロヘキシルホスフィノ−２’，６’−ジメトキシビフェニル８３０ｍｇ、トリス（ジベンジリデンアセトン）ジパラジウム４５７ｍｇ、リン酸カリウム４．３１ｇ及びエチレングリコールジメチルエーテル５０ｍＬの混合物を、窒素雰囲気下、加熱還流下で１１時間攪拌した。この反応物を室温まで冷却した後、減圧下濃縮した。残さに水を加え酢酸エチルで２回抽出し、飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥し、減圧下濃縮した。残さをシリカゲルカラムクロマトグラフィー（ヘキサン：酢酸エチル＝２：１）で精製し、４−（２−エチル−４−ベンジルオキシフェニル）−２−メチル−５，６−ジメトキシ−３（２Ｈ）−ピリダジノン１．７５ｇをオイルとして得た（収率９０％）。
^１Ｈ ＮＭＲ（ＣＤＣｌ_３）δ ｐｐｍ：1.14 (3H, t, J = 7.5 Hz), 2.37-2.58 (2H, m), 3.56 (3H, s), 3.66 (3H, s), 3.92 (3H, s), 5.08 (2H, s), 6.85 (1H, dd, J = 8.5, 2.7 Hz), 6.96 (1H, d, J = 2.7 Hz), 7.05 (1H, d, J = 8.5 Hz), 7.33 (1H, t, J = 7.2 Hz), 7.39 (2H, t, J = 7.2 Hz), 7.45 (2H, d, J = 7.0 Hz).
参考例３−５
化合物ＩＩ−３の合成
４−（２−エチル−４−ベンジルオキシフェニル）−２，６−ジメチル−５−メトキシ−３（２Ｈ）−ピリダジノンに代えて、４−（２−エチル−４−ベンジルオキシフェニル）−２−メチル−５，６−ジメトキシ−３（２Ｈ）−ピリダジノンを用い、参考例１−５に準じて行い、化合物ＩＩ−３を得た。
^１Ｈ ＮＭＲ（ＣＤＣｌ_３）δ ｐｐｍ：1.08 (3H, t, J = 7.5 Hz), 2.32-2.49 (2H, m), 3.68 (3H, s), 3.95 (3H, s), 6.65 (1H, dd, J = 8.3, 2.6 Hz), 6.74 (1H, d, J = 2.6 Hz), 6.90 (1H, d, J = 8.3 Hz), 8.31 (1H, br s). Reference example 3
Synthesis of Compound II-3

Reference Example 3-1
Synthesis of 4,5-dichloro-6-hydroxy-2-methyl-3 (2H) -pyridazinone

To a solution of 107 g of dichloromalonic anhydride in 200 ml of THF, 29.5 g of methyl hydrazine was slowly added dropwise under ice cooling. The reaction was stirred for 2 hours under reflux with heating and then concentrated under reduced pressure. The obtained solid was washed with MTBE and acetone to obtain 100 g of 4,5-dichloro-6-hydroxy-2-methyl-3 (2H) -pyridazinone.
¹ H NMR (DMSO-d ₆ ) δ ppm: 3.54 (3H, s), 12.37 (1H, br s).
Reference Example 3-2
Synthesis of 4,5-dichloro-6-methoxy-2-methyl-3 (2H) -pyridazinone

To a mixture of 22.4 g of dimethyl sulfate, 36.8 g of cesium carbonate and 100 ml of DMF, 20 g of 4,5-dichloro-6-hydroxy-2-methyl-3 (2H) -pyridazinone was slowly added at 70 ° C. and stirred for 30 minutes. The reaction solution was poured into ice water, the resulting solid was filtered, the solid was washed successively with water and MTBE, and dried to give 4,5-dichloro-6-methoxy-2-methyl-3 (2H) -pyridazinone 15 0.1 g was obtained.
¹ H NMR (CDCl ₃ ) δ ppm: 3.72 (3H, s), 3.92 (3H, s).
Reference Example 3-3
Synthesis of 4-chloro-5,6-dimethoxy-2-methyl-3 (2H) -pyridazinone

To a mixture of 2.0 g (9.56 mmol) of 4,5-dichloro-6-methoxy-2-methyl-3 (2H) -pyridazinone and 20 ml of methanol was added 1.93 g of a 28% sodium methoxide methanol solution at room temperature. Stir for hours. The reaction solution was concentrated under reduced pressure. The obtained solid was washed with water, washed with a mixed solvent of hexane: MTBE = 3: 1, and dried to obtain 1.22 g of 4-chloro-5,6-dimethoxy-2-methyl-3 (2H) -pyridazinone. It was.
¹ H NMR (CDCl ₃ ) δ ppm: 3.68 (3H, s), 3.90 (3H, s), 4.06 (3H, s).
Reference Example 3-4
Synthesis of 4- (2-ethyl-4-benzyloxyphenyl) -2-methyl-5,6-dimethoxy-3 (2H) -pyridazinone

4-chloro-5,6-dimethoxy-2-methyl-3 (2H) -pyridazinone 1.03 g, 4-benzyloxy-2-ethylphenylboronic acid 1.42 g, 2-dicyclohexylphosphino-2 ′, 6 ′ -A mixture of 830 mg of dimethoxybiphenyl, 457 mg of tris (dibenzylideneacetone) dipalladium, 4.31 g of potassium phosphate and 50 mL of ethylene glycol dimethyl ether was stirred for 11 hours under heating and refluxing in a nitrogen atmosphere. The reaction was cooled to room temperature and concentrated under reduced pressure. Water was added to the residue, and the mixture was extracted twice with ethyl acetate, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 2: 1) to give 4- (2-ethyl-4-benzyloxyphenyl) -2-methyl-5,6-dimethoxy-3 (2H) -pyridazinone. 1.75 g was obtained as an oil (yield 90%).
¹ H NMR (CDCl ₃ ) δ ppm: 1.14 (3H, t, J = 7.5 Hz), 2.37-2.58 (2H, m), 3.56 (3H, s), 3.66 (3H, s), 3.92 (3H, s ), 5.08 (2H, s), 6.85 (1H, dd, J = 8.5, 2.7 Hz), 6.96 (1H, d, J = 2.7 Hz), 7.05 (1H, d, J = 8.5 Hz), 7.33 (1H , t, J = 7.2 Hz), 7.39 (2H, t, J = 7.2 Hz), 7.45 (2H, d, J = 7.0 Hz).
Reference Example 3-5
Synthesis of Compound II-3 4- (2-Ethyl-4-benzyloxyphenyl) -2,6-dimethyl-5-methoxy-3 (2H) -pyridazinone instead of 4- (2-ethyl-4-benzyl) Oxyphenyl) -2-methyl-5,6-dimethoxy-3 (2H) -pyridazinone was used according to Reference Example 1-5 to give compound II-3.
¹ H NMR (CDCl ₃ ) δ ppm: 1.08 (3H, t, J = 7.5 Hz), 2.32-2.49 (2H, m), 3.68 (3H, s), 3.95 (3H, s), 6.65 (1H, dd , J = 8.3, 2.6 Hz), 6.74 (1H, d, J = 2.6 Hz), 6.90 (1H, d, J = 8.3 Hz), 8.31 (1H, br s).

Next, the formulation example of this invention compound is shown.
Formulation Example 1 Wetting agent Compound I-1 of the present invention 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.

Formulation Example 2 Granules Compound I-1 of the present invention 1.5% by weight
2% by weight sodium lignin sulfonate
Talc 40% by weight
Bentonite 56.5% by weight
, Mixed with water, granulated and dried to obtain granules.

Formulation Example 3 Flowable agent Compound I-1 of the present invention 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.

Next, it is shown by test examples that the compound of the present invention has an excellent herbicidal effect.
Test Example 1 Post-emergence post-emergence treatment test A plastic cup having a diameter of 8 cm and a depth of 6.5 cm was filled with a commercial seedling culture soil, and seeds of Inobiae were sowed and covered with about 0.5 cm of soil. Cultivated for a predetermined period. When the plant grew to the 1st to 2nd leaf stage, a drug dilution solution containing the compound I-1 of the present invention was uniformly sprayed over the entire plant at a predetermined treatment dose. The drug diluent is prepared by dissolving a predetermined amount of the compound I-1 of the present invention in a dimethylformamide solution (2%) of Tween 20 (polyoxyethylene sorbitan fatty acid ester, manufactured by MP Biomedicals, Inc.) and diluting with deionized water. It was prepared by doing. Plants after chemical treatment were cultivated in a greenhouse, and after 20 days of treatment, the efficacy of controlling the Inhibiae was observed and evaluated, and was shown in 11 stages from 0 to 10 (0 was no action, 10 was completely dead, 9).
As a result, the compound I-1 of the present invention showed an efficacy of 9 or more at a treatment dose of 1,000 g / 10000 m ² .

Test Example 2 Field Germination Pretreatment Test A plastic cup having a diameter of 8 cm and a depth of 6.5 cm was filled with steam-sterilized field soil, seeded with wheat and covered with about 0.5 cm of soil. Subsequently, the chemical | medical agent dilution liquid containing this invention compound I-1 was uniformly spread | dispersed on the soil surface by the predetermined processing chemical amount. The drug diluent was prepared in the same manner as in Test Example 1. The plant after chemical treatment was cultivated in a greenhouse, and after 3 weeks of treatment, the effect of controlling the wheat was observed and evaluated.
As a result, the compound I-1 of the present invention showed an efficacy of 9 or more at a treatment dose of 1,000 g / 10000 m ² .

Test Example 3 Herbicidal Effect Test on Paddy Weeds A plastic cup with a diameter of 9 cm and a depth of 10 cm filled with steam-sterilized soil was seeded with Tainubies and cultivated in a greenhouse until a predetermined growth stage (one leaf stage). After adjusting the inundation depth to 3 cm, the drug diluted solution containing the compound I-1 of the present invention was subjected to inundation soil treatment at a predetermined treatment dose. The drug dilution solution was prepared by dissolving a predetermined amount of the compound I-1 of the present invention in an acetone solution (2%) of Tween 20 (polyoxyethylene sorbitan fatty acid ester, manufactured by MP Biomedicals, Inc.) and deionized water. Prepared by dilution. Plants after chemical treatment were cultivated in a greenhouse, and after 20 days of treatment, the effectiveness of weed control was observed and evaluated, and was shown in 11 stages from 0 to 10 (0 was no action, 10 was completely dead, the middle was equal, etc. The interval was evaluated from 1 to 9).
As a result, the compound I-1 of the present invention showed an efficacy of 9 or more at a treatment dose of 1,000 g / 10000 m ² .

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

Claims (11)

Formula (I)

[Wherein R ¹ is hydrogen, C _1-6 alkyl group, C _3-8 cycloalkyl group, (C _3-8 cycloalkyl) C _1-6 alkyl group, C _3-4 alkenyl group or C _3-4 Represents an alkynyl group,
R ² is hydrogen, halogen, cyano group, nitro group, C _1-6 alkyl group, C _1-6 haloalkyl group, C _1-6 alkoxy group, C _1-6 haloalkoxy group, C _1-6 alkylthio group, C _{1-6 1-6} alkylsulfinyl group, C _1-6 alkylsulfonyl group, C _1-6 haloalkylthio group, C _1-6 haloalkylsulfinyl group, C _1-6 haloalkylsulfonyl group, C _3-8 cycloalkyl group, C _{3- 8} cycloalkoxy groups, (C _3-8 cycloalkyl) C _1-6 alkoxy groups, (C _1-6 alkylthio) C _1-6 alkoxy groups, (C _1-6 alkoxy) C _1-6 alkoxy groups, C _{3 -6} alkenyloxy group, C _3-6 alkynyloxy group, cyano C _1-6 alkoxy group, (C _1-6 alkoxy) carbonyl C _1-6 alkoxy group, carbamoyl C _1-6 alkoxy group, {(C _{1- 6} alkyl) amino carbonyl} C _1-6 alkoxy group, {di ( _1-6 alkyl) amino carbonyl} C _1-6 alkoxy group, an amino group, C _1-6 alkylamino group, di (C _1-6 alkyl) amino group, formylamino group, (C _1-6 alkyl) carbonylamino Group, hydroxy C _1-6 alkyl group, (C _1-6 alkoxy) C _1-6 alkyl group, (C _1-6 haloalkoxy) C _1-6 alkyl group, (C _3-8 cycloalkoxy) C _{1- 6} alkyl group, {(C _3-8 cycloalkyl) C _1-6 alkoxy} C _1-6 alkyl group, (C _1-6 alkylthio) C _1-6 alkyl group, (C _1-6 haloalkylthio) C _{1 -6} alkyl group, cyano C _1-6 alkyl group, hydroxyimino C _1-6 alkyl group, (C _1-6 alkoxy) imino C _1-6 alkyl group, formyl group or (C _1-6 alkyl) carbonyl group Represent,
R ³ is halogen, C _1-3 alkyl group, C _1-3 haloalkyl group, C _2-4 alkenyl group, C _2-4 alkynyl group, C _1-3 alkoxy group, C _1-3 haloalkoxy group or C _{3 Represents} an _-8 cycloalkyl group,
R ⁴ and R ⁵ may be the same or different and are hydrogen, halogen, C _1-3 alkyl group, C _1-3 haloalkyl group, C _2-4 alkenyl group, C _2-4 alkynyl group, C _1-3 Represents an alkoxy group, a C _1-3 haloalkoxy group or a C _3-8 cycloalkyl group,
A represents an aryl group of a monocyclic or bicyclic fused ring, or a heterocycle of a monocyclic or bicyclic fused ring containing one or more atoms selected from the group consisting of nitrogen, oxygen and sulfur as a hetero atom. Represents an aryl group, and these groups may have one or more atoms or groups selected from group B;
G is the following formula

{Wherein R ⁶ is one or more selected from a C _1-6 alkyl group, a C _1-3 haloalkyl group, a C _3-6 cycloalkyl group, a C _2-6 alkenyl group, a C _2-6 alkynyl group, and a group C. atom or optionally C _6-10 aryl group optionally having a group (one or more atoms optionally C _6-10 aryl optionally having a group selected from group C) C _1-6 alkyl group or Represents a 5-6 membered heteroaryl group,
R ⁷ represents a phenyl group which may have one or more atoms or groups selected from Group C. }
Represents any group represented by
Group B: halogen, C _1-3 alkyl group, C _1-3 haloalkyl group, C _1-3 alkoxy group, C _1-3 haloalkoxy group, C _3-8 cycloalkyl group, C _2-4 alkenyl group, C _2-4 haloalkenyl, C _2-4 alkynyl group, C _1-3 alkylthio group, C _1-3 haloalkylthio group, C _1-3 alkylsulfinyl group, C _1-3 haloalkylsulfinyl group, C _1-3 alkyl Sulfonyl group, C _1-3 haloalkylsulfonyl group, nitro group, cyano group, (C _1-6 alkyl) carbonyl group, (C _1-6 alkoxy) carbonyl group, carbamoyl group, (C _1-3 alkyl) aminocarbonyl group Di (C _1-3 alkyl) aminocarbonyl group, (C _1-6 alkyl) carbonylamino group, (C _3-8 cycloalkyl) carbonylamino group, (C _1-6 alkoxy) carbonylamino group, and (C _1-3 alkoxy) C _1-3 Al The group consisting of Le group.
Group C: a group consisting of halogen, C _1-3 alkyl group, C _1-3 haloalkyl group, C _1-3 alkoxy group and nitro group. ] The pyridazinone compound shown by this. A represents a phenyl group, a naphthyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a benzothiazolyl group, a benzoxazolyl group, a quinolinyl group, a cinnolinyl group, a quinazolinyl group, a quinoxalinyl group, or a benzotriazinyl group. The group may have one or more atoms or groups selected from group B,
The pyridazinone compound according to claim 1, wherein the group B is a halogen, a C _1-3 alkyl group, a C _1-3 haloalkyl group, a C _1-3 alkoxy group, a C _1-3 haloalkoxy group, a nitro group, or a cyano group. R ² is hydrogen, C _1-3 alkyl group, C _1-3 haloalkyl group, C _1-6 alkoxy group, C _1-6 haloalkoxy group, C _3-8 cycloalkyl group, C _3-8 cycloalkoxy group or The pyridazinone compound according to claim 2, which is a (C _3-8 cycloalkyl) C _1-6 alkoxy group. The pyridazinone compound according to claim ² , wherein R ² is hydrogen, a methyl group or a methoxy group. The pyridazinone compound according to claim 4, wherein R ¹ is a methyl group. R ¹ is a methyl group,
R ² is hydrogen, a methyl group or a methoxy group,
R ³ is a methyl group, an ethyl group, a propyl group, a cyclopropyl group, a halogen or a halomethyl group,
R ⁴ is hydrogen or a methyl group,
R ⁵ is hydrogen, methyl group, ethyl group, propyl group, cyclopropyl group, halogen or halomethyl group,
A is a phenyl group, naphthyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, benzothiazolyl group, benzoxazolyl group, quinolinyl group, cinnolinyl group, quinazolinyl group, quinoxalinyl group or benzotriazinyl group, these The group may have one or more atoms or groups selected from group B,
G may have (C _1-6 alkyl) carbonyl group, C _1-3 haloalkylcarbonyl group, (C _3-6 cycloalkyl) carbonyl group, phenyl optionally having one or more atoms or groups selected from group D It may have a carbonyl group, (phenyl _optionally having one or more atoms or groups selected from group D) C _1-6 alkyl group, or (one or more atoms or groups selected from group D). Phenyl) methyl group,
The pyridazinone compound according to claim 1, wherein group D is halogen, a C _1-3 alkyl group, a C _1-3 haloalkyl group, a C _1-3 alkoxy group, a nitro group, or a cyano group.   The pyridazinone compound according to claim 6, wherein A is a pyridyl group, a benzothiazolyl group, a benzoxazolyl group or a quinolinyl group, and these groups may have one or more atoms or groups selected from Group B. R ³ is a methyl group, an ethyl group, a propyl group, a cyclopropyl group,
R ⁴ and R ⁵ are hydrogen,
The pyridazinone compound according to claim 6, wherein A is a pyridyl group, a benzothiazolyl group, a benzooxazolyl group or a quinolinyl group, and these groups may have one or more atoms or groups selected from Group B.   A herbicide containing the pyridazinone compound according to any one of claims 1 to 8 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 8 is applied to weeds or soil in which weeds grow.   Use of the pyridazinone compound according to any one of claims 1 to 8 for controlling weeds.