JP2008133252A - Pyridazinone compound and herbicide containing the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a compound having excellent herbicidal efficiency, and a herbicide containing the compound. <P>SOLUTION: The pyridazinone compound is represented by general formula (I) (wherein, R<SP>1</SP>is a 1-6C alkyl group or a (1-6C alkyloxy)-1-6C alkyl group; R<SP>2</SP>is a hydrogen atom or a 1-6C alkyl group; G is a hydrogen atom or the like; Z<SP>1</SP>is a 1-6C alkyl group; Z<SP>2</SP>is a 1-6C alkyl group; n is 0, 1, 2, 3 or 4; with the proviso that the total number of carbon atoms in the groups represented by Z<SP>1</SP>and n Z<SP>2</SP>s is ≥2). The herbicide contains the compound. <P>COPYRIGHT: (C)2008,JPO&INPIT

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 widely promoted, and compounds having the effect of controlling weeds have been found.
Moreover, a certain kind of pyridazinone compound (refer nonpatent literature 1) is known.

Journal of Heterocyclic Chemistry (J. Heterocycl. Chem.), 42, 427-435 (2005)

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

〔式中、Ｒ¹ はＣ_1-6アルキル基又は（Ｃ_1-6アルキルオキシ）Ｃ_1-6アルキル基を表し、
Ｒ² は水素原子又はＣ_1-6アルキル基を表し、
Ｇは水素原子又は下記式

｛式中、Ｌは酸素原子又はイオウ原子を表し、
Ｒ³はＣ_1-6アルキル基、Ｃ_3-8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_6-10アリール基、（Ｃ_6-10アリール）Ｃ_1-6アルキル基、Ｃ_1-6アルキルオキシ基、Ｃ_3-8シクロアルキルオキシ基、Ｃ_2-6アルケニルオキシ基、Ｃ_2-6アルキニルオキシ基、Ｃ_6-10アリールオキシ基、（Ｃ_6-10アリール）Ｃ_1-6アルキルオキシ基、アミノ基、Ｃ_1-6アルキルアミノ基、Ｃ_2-6アルケニルアミノ基、Ｃ_6-10アリールアミノ基、ジ（Ｃ_1-6アルキル）アミノ基、ジ（Ｃ_2-6アルケニル）アミノ基、（Ｃ_1-6アルキル）（Ｃ_6-10アリール）アミノ基又は３〜８員の含窒素複素環基を表し、
Ｒ⁴はＣ_1-6アルキル基、Ｃ_6-10アリール基、Ｃ_1-6アルキルアミノ基又はジ（Ｃ_1-6アルキル）アミノ基を表し、
Ｒ⁵及びＲ⁶は同一又は異なっていてもよく、Ｃ_1-6アルキル基、Ｃ_3-8シクロアルキル基、Ｃ_2-6アルケニル基、Ｃ_6-10アリール基、Ｃ_1-6アルキルオキシ基、Ｃ_3-8シクロアルキルオキシ基、Ｃ_6-10アリールオキシ基、（Ｃ_6-10アリール）Ｃ_1-6アルキルオキシ基、Ｃ_1-6アルキルチオ基、Ｃ_1-6アルキルアミノ基又はジ（Ｃ_1-6アルキル）アミノ基を表す。
但し、Ｒ³、Ｒ⁴、Ｒ⁵及びＲ⁶で表されるいずれの基もハロゲン原子により置換されていてもよく、Ｃ_3-8シクロアルキル基、Ｃ_6-10アリール基、（Ｃ_6-10アリール）Ｃ_1-6アルキル基のアリール部分、Ｃ_3-8シクロアルキルオキシ基、Ｃ_6-10アリールオキシ基、（Ｃ_6-10アリール）Ｃ_1-6アルキルオキシ基のアリール部分、Ｃ_6-10アリールアミノ基のアリール部分、（Ｃ_1-6アルキル）（Ｃ_6-10アリール）アミノ基のアリール部分及び３〜８員の含窒素複素環基はＣ_1-6アルキル基により置換されていてもよい。｝
で表されるいずれかの基を表し、
Ｚ¹はＣ_1-6アルキル基を表し、Ｚ²はＣ_1-6アルキル基を表し、ｎは０、１、２、３又は４を表し、ｎが２以上の整数を表す場合、各々のＺ²は同一又は異なっていてもよい。
但し、Ｚ¹及びｎ個のＺ²で表される基における炭素原子数の合計は２以上である。〕
で示されるピリダジノン化合物（以下、本発明化合物と記す。）、本発明化合物を有効成分として含有する除草剤、本発明化合物の有効量を雑草又は雑草の生育する土壌に施用する雑草の防除方法、本発明化合物の雑草防除のための使用及び本発明化合物の製造のための製造中間体化合物を提供する。本発明化合物には、一般式（Ｉ）で示されるピリダジノン化合物が無機塩基等と混合されて農学的に許容される塩の形態をとる場合もあるが、本発明には該塩の形態のピリダジノン化合物も包含される。 As a result of intensive studies, the present inventors have found that the pyridazinone compound represented by the general formula (I) has an excellent weed control effect, and have reached the present invention.
The present invention relates to general formula (I)

[Wherein R ¹ represents a C _1-6 alkyl group or a (C _1-6 alkyloxy) C _1-6 alkyl group,
R ² represents a hydrogen atom or a C _1-6 alkyl group,
G is a hydrogen atom or the following formula

{Wherein L represents an oxygen atom or a sulfur atom,
R ³ is a C _1-6 alkyl group, C _3-8 cycloalkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _6-10 aryl group, (C _6-10 aryl) C _1-6 Alkyl group, C _1-6 alkyloxy group, C _3-8 cycloalkyloxy group, C _2-6 alkenyloxy group, C _2-6 alkynyloxy group, C _6-10 aryloxy group, (C _6-10 aryl) ) C _1-6 alkyloxy group, amino group, C _1-6 alkylamino group, C _2-6 alkenylamino group, C _6-10 arylamino group, di (C _1-6 alkyl) amino group, di (C _2-6 alkenyl) amino group, (C _1-6 alkyl) (C _6-10 aryl) amino group or 3-8 membered nitrogen-containing heterocyclic group,
R ⁴ represents a C _1-6 alkyl group, a C _6-10 aryl group, a C _1-6 alkylamino group or a di (C _1-6 alkyl) amino group,
R ⁵ and R ⁶ may be the same or different and are a C _1-6 alkyl group, a C _3-8 cycloalkyl group, a C _2-6 alkenyl group, a C _6-10 aryl group, a C _1-6 alkyloxy group. C _3-8 cycloalkyloxy group, C _6-10 aryloxy group, (C _6-10 aryl) C _1-6 alkyloxy group, C _1-6 alkylthio group, C _1-6 alkylamino group or di ( C _1-6 alkyl) represents an amino group.
However, any group represented by R ³ , R ⁴ , R ⁵ and R ⁶ may be substituted with a halogen atom, and may be a C _3-8 cycloalkyl group, a C _6-10 aryl group, (C _{6- 10} aryl) C _1-6 alkyl group aryl moiety, C _3-8 cycloalkyloxy group, C _6-10 aryloxy group, (C _6-10 aryl) C _1-6 alkyloxy group aryl moiety, C _{6 The} aryl moiety of the _-10 arylamino group, the aryl moiety of the (C _1-6 alkyl) (C _6-10 aryl) amino group, and the 3- to 8-membered nitrogen-containing heterocyclic group are substituted with a C _1-6 alkyl group. May be. }
Any one of the groups represented by
Z ¹ represents a C _1-6 alkyl group, Z ² represents a C _1-6 alkyl group, n represents 0, 1, 2, 3 or 4, and when n represents an integer of 2 or more, Z ² may be the same or different.
However, the total number of carbon atoms in the group represented by Z ¹ and n Z ² is 2 or more. ]
A herbicide containing the compound of the present invention as an active ingredient, a method for controlling weeds, wherein an effective amount of the compound of the present invention is applied to weed or soil where weeds grow, Use of the compounds of the present invention for weed control and production intermediate compounds for the production of the compounds of the present invention are provided. The compound of the present invention may take the form of an agriculturally acceptable salt by mixing the pyridazinone compound represented by the general formula (I) with an inorganic base or the like. Also included are compounds.

  Weeds can be controlled by applying an effective amount of the compound of the present invention to weeds or soil where weeds grow.

In the substituent represented by R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , Z ¹ and Z ² in the general formula (I) of the present invention,
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, isohexyl group and the like.
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, a cyclohexyl group,
The C _2-6 alkenyl group means an alkenyl group having 2 to 6 carbon atoms, and examples thereof include an allyl group, 1-buten-3-yl group, 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 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 a C _1-6 alkyl group substituted with a C _6-10 aryl group, and examples thereof include a benzyl group and a phenethyl group.
The C _1-6 alkyloxy group means an alkyloxy group having 1 to 6 carbon atoms, and examples thereof include a methoxy group, an ethoxy group, a propoxy group, and an isopropoxy group.
The C _3-8 cycloalkyloxy group means a cycloalkyloxy group having 3 to 8 carbon atoms, and examples thereof include a cyclopropyloxy group and a cyclopentyloxy group.
C _2-6 alkenyloxy group means an alkenyloxy group having 2 to 6 carbon atoms, and examples thereof include a vinyloxy group and an allyloxy group.
The C _2-6 alkynyloxy group means an alkynyloxy group having 2 to 6 carbon atoms, and examples thereof include a propargyloxy group and a 2-butynyloxy group.
The C _6-10 aryloxy group means an aryloxy group having 6 to 10 carbon atoms, and examples thereof include a phenoxy group and a naphthyloxy group.
(C _6-10 aryl) C _1-6 alkyloxy group means a C _1-6 alkyloxy group substituted with a C _6-10 aryl group, and examples thereof include a benzyloxy group and a phenethyloxy group. And
C _1-6 alkylamino group means an alkylamino group having 1 to 6 carbon atoms, and examples thereof include a methylamino group and an ethylamino group.
The C _2-6 alkenylamino group means an alkenylamino group having 2 to 6 carbon atoms, and examples thereof include an allylamino group and a 3-butenylamino group.
The C _6-10 arylamino group means an arylamino group having 6 to 10 carbon atoms, and examples thereof include a phenylamino group and a naphthylamino group.
The di (C _1-6 alkyl) amino group means an amino group substituted with two identical or different C _1-6 alkyl groups. For example, dimethylamino group, diethylamino group, N-ethyl-N— Methylamino group, etc.
The di (C _2-6 alkenyl) amino group means an amino group substituted by two identical or different C _2-6 alkenyl groups, such as diallylamino group, di (3-butenyl) amino group, etc. Are mentioned,
The (C _1-6 alkyl) (C _6-10 aryl) amino group means an amino group substituted with a C _1-6 alkyl group and a C _6-10 aryl group. For example, a methylphenylamino group, ethyl Phenylamino group and the like,
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, a propylthio group, and an isopropylthio group.
(C _1-6 alkyloxy) The C _1-6 alkyl group means a C _1-6 alkyl group substituted with a C _1-6 alkyloxy group, and examples thereof include a methoxyethyl group and an ethoxyethyl group. And
The 3- to 8-membered nitrogen-containing heterocyclic group contains 1 to 3 nitrogen atoms, may further contain 1 to 3 oxygen atoms and / or sulfur atoms, and is aromatic or alicyclic. It means a 3- to 8-membered heterocyclic group, and examples thereof include 1-pyrazolyl group, 2-pyridyl group, 2-pyrimidinyl group, 2-thiazolyl group, pyrrolidino group, piperidino group, morpholino group and the like.
Examples of the halogen atom with which the groups represented by R ³ , R ⁴ , R ⁵ and R ⁶ may be substituted include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
An aryl part of a C _3-8 cycloalkyl group, a C _6-10 aryl group, a (C _6-10 aryl) C _1-6 alkyl group in the groups represented by R ³ , R ⁴ , R ⁵ and R ⁶ ; A C _3-8 cycloalkyloxy group, a C _6-10 aryloxy group, an aryl moiety of a (C _6-10 aryl) C _1-6 alkyloxy group, an aryl moiety of a C _6-10 arylamino group, (C _{1- 6} alkyl) (C _6-10 aryl) A C _1-6 alkyl group in which the aryl portion of the amino group and the 3- to 8-membered nitrogen-containing heterocyclic group which may be substituted is, for example, a methyl group, an ethyl group, A propyl group, a butyl group, etc. are mentioned.

Among the compounds of the present invention, the compound represented by the general formula (Ia) in which G is a hydrogen atom is a tautomer represented by the general formula (Ia ′) and the general formula (Ia ″). Can exist. The compound represented by the general formula (Ia) includes all of these tautomers and a mixture of any two or more thereof.

  In addition, the compound represented by the general formula (Ia) is an inorganic base (for example, alkali metal (lithium, sodium, potassium, etc.) hydroxide, carbonate, bicarbonate, acetate, hydride, alkali, etc. Earth metal (magnesium, calcium, barium, etc.) hydroxide, hydride, ammonia), organic base (eg, dimethylamine, triethylamine, piperazine, pyrrolidine, piperidine, 2-phenylethylamine, benzylamine, ethanolamine, Diethanolamine, pyridine, collidine, etc.), metal alkoxides (for example, sodium methoxide, potassium tert-butoxide, magnesium methoxide, etc.) and the like may be mixed to take the form of an agriculturally acceptable salt. The compound represented by the general formula (Ia) also includes pyridazinone compounds in the form of such agriculturally acceptable salts.

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.

｛式中、Ｒ^3bはＣ_1-6アルキル基、Ｃ_3-8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_6-10アリール基、（Ｃ_6-10アリール）Ｃ_1-6アルキル基、Ｃ_1-6アルキルオキシ基、Ｃ_3-8シクロアルキルオキシ基、Ｃ_6-10アリールオキシ基、（Ｃ_6-10アリール）Ｃ_1-6アルキルオキシ基、Ｃ_1-6アルキルアミノ基、Ｃ_6-10アリールアミノ基又はジ（Ｃ_1-6アルキル）アミノ基を表し、
Ｒ^4bはＣ_1-6アルキル基又はＣ_6-10アリール基を表し、
Ｒ^5b及びＲ^6bは同一又は異なっていてもよく、Ｃ_1-6アルキル基、Ｃ_1-6アルキルオキシ基、Ｃ_6-10アリールオキシ基又はＣ_1-6アルキルチオ基を表す。
但し、Ｒ^3b、Ｒ^4b、Ｒ^5b及びＲ^6bで表されるいずれの基もハロゲン原子により置換されていてもよく、Ｃ_3-8シクロアルキル基、Ｃ_6-10アリール基、（Ｃ_6-10アリール）Ｃ_1-6アルキル基のアリール部分、Ｃ_3-8シクロアルキルオキシ基、Ｃ_6-10アリールオキシ基、（Ｃ_6-10アリール）Ｃ_1-6アルキルオキシ基のアリール部分、Ｃ_6-10アリールアミノ基のアリール部分はＣ_1-6アルキル基により置換されていてもよい。｝
で表されるいずれかの基であるピリダジノン化合物。
一般式（Ｉ）において、Ｇが水素原子又は下記式

｛式中、Ｒ^3aはＣ_1-6アルキル基、Ｃ_3-8シクロアルキル基、Ｃ_6-10アリール基、Ｃ_1-6アルキルオキシ基又はジ（Ｃ_1-6アルキル）アミノ基を表し、
Ｒ^4aはＣ_1-6アルキル基を表す。
但し、Ｒ^3a及びＲ^4aで表されるいずれの基もハロゲン原子により置換されていてもよく、Ｃ_3-8シクロアルキル基及びＣ_6-10アリール基はＣ_1-6アルキル基により置換されていてもよい。｝
で表されるいずれかの基であるピリダジノン化合物。
一般式（Ｉ）において、Ｒ¹がＣ_1-3アルキル基又は（Ｃ_1-3アルキルオキシ）Ｃ_1-3アルキル基であるピリダジノン化合物。
一般式（Ｉ）において、Ｒ²が水素原子又はＣ_1-3アルキル基であるピリダジノン化合物。
一般式（Ｉ）において、Ｒ²が水素原子又はメチル基であるピリダジノン化合物。
一般式（Ｉ）において、Ｚ¹ がＣ_1-3アルキル基であり、Ｚ² がＣ_1-3アルキル基であるピリダジノン化合物。 As a preferable aspect of this invention compound, the aspect shown below is mentioned, for example.
A pyridazinone compound represented by the general formula (I), wherein n is an integer of 1 or more.
A pyridazinone compound represented by the formula (I), wherein n is 0 and Z ¹ is a C _2-6 alkyl group.
A pyridazinone compound represented by the formula (I), wherein n is 1 or 2, and the bonding position of Z ² is the 4-position and / or the 6-position on the benzene ring.
In general formula (I), G is a hydrogen atom or the following formula

{Wherein R ^3b is a C _1-6 alkyl group, a C _3-8 cycloalkyl group, a C _2-6 alkenyl group, a C _2-6 alkynyl group, a C _6-10 aryl group, (C _6-10 aryl) C _1-6 alkyl group, C _1-6 alkyloxy group, C _3-8 cycloalkyloxy group, C _6-10 aryloxy group, (C _6-10 aryl) C _1-6 alkyloxy group, C _{1- Represents a 6} alkylamino group, a C _6-10 arylamino group or a di (C _1-6 alkyl) amino group,
R ^4b represents a C _1-6 alkyl group or a C _6-10 aryl group,
R ^5b and R ^6b may be the same or different and each represents a C _1-6 alkyl group, a C _1-6 alkyloxy group, a C _6-10 aryloxy group, or a C _1-6 alkylthio group.
However, any group represented by R ^3b , R ^4b , R ^5b and R ^6b may be substituted with a halogen atom, and may be a C _3-8 cycloalkyl group, a C _6-10 aryl group, (C _{6- 10} aryl) C _1-6 alkyl group aryl moiety, C _3-8 cycloalkyloxy group, C _6-10 aryloxy group, (C _6-10 aryl) C _1-6 alkyloxy group aryl moiety, C ₆ The aryl moiety of the _-10 arylamino group may be substituted with a C _1-6 alkyl group. }
The pyridazinone compound which is any group represented by these.
In general formula (I), G is a hydrogen atom or the following formula

{Wherein R ^3a represents a C _1-6 alkyl group, a C _3-8 cycloalkyl group, a C _6-10 aryl group, a C _1-6 alkyloxy group or a di (C _1-6 alkyl) amino group,
R ^4a represents a C _1-6 alkyl group.
However, any group represented by R ^3a and R ^4a may be substituted with a halogen atom, and the C _3-8 cycloalkyl group and the C _6-10 aryl group are substituted with a C _1-6 alkyl group. May be. }
The pyridazinone compound which is any group represented by these.
A pyridazinone compound represented by the general formula (I), wherein R ¹ is a C _1-3 alkyl group or a (C _1-3 alkyloxy) C _1-3 alkyl group.
A pyridazinone compound represented by the general formula (I), wherein R ² is a hydrogen atom or a C _1-3 alkyl group.
A pyridazinone compound represented by the general formula (I), wherein R ² is a hydrogen atom or a methyl group.
A pyridazinone compound represented by the general formula (I), wherein Z ¹ is a C _1-3 alkyl group and Z ² is a C _1-3 alkyl group.

｛式中、Ｒ^3b、Ｒ^4b、Ｒ^5b及びＲ^6bは前記と同じ意味を表す。｝
で表されるいずれかの基であるピリダジノン化合物。
一般式（Ｉ）において、Ｒ²が水素原子又はＣ_1-3アルキル基であり、Ｇが水素原子又は下記式

｛式中、Ｒ^3a及びＲ^4aは前記と同じ意味を表す。｝
で表されるいずれかの基であるピリダジノン化合物。
一般式（Ｉ）において、Ｒ²が水素原子又はメチル基であり、Ｇが水素原子又は下記式

｛式中、Ｒ^3b、Ｒ^4b、Ｒ^5b及びＲ^6bは前記と同じ意味を表す。｝
で表されるいずれかの基であるピリダジノン化合物。
一般式（Ｉ）において、Ｒ²が水素原子又はメチル基であり、Ｇが水素原子又は下記式

｛式中、Ｒ^3a及びＲ^4aは前記と同じ意味を表す。｝
で表されるいずれかの基であるピリダジノン化合物。
一般式（Ｉ）において、Ｒ¹がＣ_1-3アルキル基又は（Ｃ_1-3アルキルオキシ）Ｃ_1-3アルキル基であり、Ｒ²が水素原子又はＣ_1-3アルキル基であり、Ｇが水素原子又は下記式

｛式中、Ｒ^3b、Ｒ^4b、Ｒ^5b及びＲ^6bは前記と同じ意味を表す。｝
で表されるいずれかの基であるピリダジノン化合物。
一般式（Ｉ）において、Ｒ¹がＣ_1-3アルキル基又は（Ｃ_1-3アルキルオキシ）Ｃ_1-3アルキル基であり、Ｒ²が水素原子又はＣ_1-3アルキル基であり、Ｇが水素原子又は下記式

｛式中、Ｒ^3a及びＲ^4aは前記と同じ意味を表す。｝
で表されるいずれかの基であるピリダジノン化合物。
一般式（Ｉ）において、Ｒ¹がＣ_1-3アルキル基又は（Ｃ_1-3アルキルオキシ）Ｃ_1-3アルキル基であり、Ｒ²が水素原子又はメチル基であり、Ｇが水素原子又は下記式

｛式中、Ｒ^3b、Ｒ^4b、Ｒ^5b及びＲ^6bは前記と同じ意味を表す。｝
で表されるいずれかの基であるピリダジノン化合物。
一般式（Ｉ）において、Ｒ¹がＣ_1-3アルキル基又は（Ｃ_1-3アルキルオキシ）Ｃ_1-3アルキル基であり、Ｒ²が水素原子又はメチル基であり、Ｇが水素原子又は下記式

｛式中、Ｒ^3a及びＲ^4aは前記と同じ意味を表す。｝
で表されるいずれかの基であるピリダジノン化合物。 A pyridazinone compound in which R ¹ is a C _1-3 alkyl group or (C _1-3 alkyloxy) C _1-3 alkyl group and R ² is a hydrogen atom or a C _1-3 alkyl group in the general formula (I) .
A pyridazinone compound represented by the general formula (I), wherein R ¹ is a C _1-3 alkyl group or a (C _1-3 alkyloxy) C _1-3 alkyl group, and R ² is a hydrogen atom or a methyl group.
In the general formula (I), R ² is a hydrogen atom or a C _1-3 alkyl group, G is a hydrogen atom or the following formula

{Wherein, R ^3b , R ^4b , R ^5b and R ^6b represent the same meaning as described above. }
The pyridazinone compound which is any group represented by these.
In the general formula (I), R ² is a hydrogen atom or a C _1-3 alkyl group, G is a hydrogen atom or the following formula

{Wherein R ^3a and R ^4a represent the same meaning as described above. }
The pyridazinone compound which is any group represented by these.
In the general formula (I), R ² is a hydrogen atom or a methyl group, G is a hydrogen atom or the following formula

{Wherein, R ^3b , R ^4b , R ^5b and R ^6b represent the same meaning as described above. }
The pyridazinone compound which is any group represented by these.
In the general formula (I), R ² is a hydrogen atom or a methyl group, G is a hydrogen atom or the following formula

{Wherein R ^3a and R ^4a represent the same meaning as described above. }
The pyridazinone compound which is any group represented by these.
In the general formula (I), R ¹ is a C _1-3 alkyl group or a (C _1-3 alkyloxy) C _1-3 alkyl group, R ² is a hydrogen atom or a C _1-3 alkyl group, and G Is a hydrogen atom or the following formula

{Wherein, R ^3b , R ^4b , R ^5b and R ^6b represent the same meaning as described above. }
The pyridazinone compound which is any group represented by these.
In the general formula (I), R ¹ is a C _1-3 alkyl group or a (C _1-3 alkyloxy) C _1-3 alkyl group, R ² is a hydrogen atom or a C _1-3 alkyl group, and G Is a hydrogen atom or the following formula

{Wherein R ^3a and R ^4a represent the same meaning as described above. }
The pyridazinone compound which is any group represented by these.
In the general formula (I), R ¹ is a C _1-3 alkyl group or a (C _1-3 alkyloxy) C _1-3 alkyl group, R ² is a hydrogen atom or a methyl group, and G is a hydrogen atom or Following formula

{Wherein, R ^3b , R ^4b , R ^5b and R ^6b represent the same meaning as described above. }
The pyridazinone compound which is any group represented by these.
In the general formula (I), R ¹ is a C _1-3 alkyl group or a (C _1-3 alkyloxy) C _1-3 alkyl group, R ² is a hydrogen atom or a methyl group, and G is a hydrogen atom or Following formula

{Wherein R ^3a and R ^4a represent the same meaning as described above. }
The pyridazinone compound which is any group represented by these.

｛式中、Ｒ^3b、Ｒ^4b、Ｒ^5b及びＲ^6bは前記と同じ意味を表す。｝
で表されるいずれかの基であり、
ｎが０、１又は２の整数を表し、ｎが２を表す場合、２つのＺ²は同一又は異なっていてもよく、ｎが１又は２を表す場合、Ｚ²の結合位置がベンゼン環上の４位及び／又は６位であり、
Ｚ¹がＣ_1-6アルキル基（更に好ましくはＣ_1-3アルキル基）であり、
Ｚ²がＣ_1-6アルキル基（更に好ましくはＣ_1-3アルキル基）であるピリダジノン化合物。
一般式（Ｉ）において、Ｒ¹がＣ_1-3アルキル基又は（Ｃ_1-3アルキルオキシ）Ｃ_1-3アルキル基であり、Ｒ²が水素原子又はＣ_1-3アルキル基であり、Ｇが水素原子又は下記式

｛式中、Ｒ^3a及びＲ^4aは前記と同じ意味を表す。｝
で表されるいずれかの基であり、
ｎが０、１又は２の整数を表し、ｎが２を表す場合、２つのＺ²は同一又は異なっていてもよく、ｎが１又は２を表す場合、Ｚ²の結合位置がベンゼン環上の４位及び／又は６位であり、
Ｚ¹がＣ_1-6アルキル基（更に好ましくはＣ_1-3アルキル基）であり、
Ｚ²がＣ_1-6アルキル基（更に好ましくはＣ_1-3アルキル基）であるピリダジノン化合物。 In the general formula (I), R ¹ is a C _1-3 alkyl group or a (C _1-3 alkyloxy) C _1-3 alkyl group, R ² is a hydrogen atom or a C _1-3 alkyl group,
When n represents an integer of 0, 1 or 2, and n represents 2, two Z ² may be the same or different. When n represents 1 or 2, the bonding position of Z ² is on the benzene ring. 4th and / or 6th
Z ¹ is a C _1-6 alkyl group (more preferably a C _1-3 alkyl group),
A pyridazinone compound in which Z ² is a C _1-6 alkyl group (more preferably a C _1-3 alkyl group).
In the general formula (I), R ¹ is a C _1-3 alkyl group or a (C _1-3 alkyloxy) C _1-3 alkyl group, R ² is a hydrogen atom or a C _1-3 alkyl group, and G Is a hydrogen atom or the following formula

{Wherein, R ^3b , R ^4b , R ^5b and R ^6b represent the same meaning as described above. }
Any of the groups represented by
When n represents an integer of 0, 1 or 2, and n represents 2, two Z ² may be the same or different. When n represents 1 or 2, the bonding position of Z ² is on the benzene ring. 4th and / or 6th
Z ¹ is a C _1-6 alkyl group (more preferably a C _1-3 alkyl group),
A pyridazinone compound in which Z ² is a C _1-6 alkyl group (more preferably a C _1-3 alkyl group).
In the general formula (I), R ¹ is a C _1-3 alkyl group or a (C _1-3 alkyloxy) C _1-3 alkyl group, R ² is a hydrogen atom or a C _1-3 alkyl group, and G Is a hydrogen atom or the following formula

{Wherein R ^3a and R ^4a represent the same meaning as described above. }
Any of the groups represented by
When n represents an integer of 0, 1 or 2, and n represents 2, two Z ² may be the same or different. When n represents 1 or 2, the bonding position of Z ² is on the benzene ring. 4th and / or 6th
Z ¹ is a C _1-6 alkyl group (more preferably a C _1-3 alkyl group),
A pyridazinone compound in which Z ² is a C _1-6 alkyl group (more preferably a C _1-3 alkyl group).

｛式中、Ｒ^3b、Ｒ^4b、Ｒ^5b及びＲ^6bは前記と同じ意味を表す。｝
で表されるいずれかの基であり、
ｎが０、１又は２の整数を表し、ｎが２を表す場合、２つのＺ²は同一又は異なっていてもよく、ｎが１又は２を表す場合、Ｚ²の結合位置がベンゼン環上の４位及び／又は６位であり、
Ｚ¹がＣ_1-6アルキル基（更に好ましくはＣ_1-3アルキル基）であり、
Ｚ²がＣ_1-6アルキル基（更に好ましくはＣ_1-3アルキル基）であるピリダジノン化合物。
一般式（Ｉ）において、Ｒ¹がＣ_1-3アルキル基又は（Ｃ_1-3アルキルオキシ）Ｃ_1-3アルキル基であり、Ｒ²が水素原子又はメチル基であり、Ｇが水素原子又は下記式

｛式中、Ｒ^3a及びＲ^4aは前記と同じ意味を表す。｝
で表されるいずれかの基であり、
ｎが０、１又は２の整数を表し、ｎが２を表す場合、２つのＺ²は同一又は異なっていてもよく、ｎが１又は２を表す場合、Ｚ²の結合位置がベンゼン環上の４位及び／又は６位であり、
Ｚ¹がＣ_1-6アルキル基（更に好ましくはＣ_1-3アルキル基）であり、
Ｚ²がＣ_1-6アルキル基（更に好ましくはＣ_1-3アルキル基）であるピリダジノン化合物。
一般式（Ｉ−１）

において、Ｒ^2-1が水素原子又はＣ_1-3アルキル基であり、Ｇ¹が水素原子、ハロゲン原子で置換されていてもよいＣ_1-3アルキルカルボニル基、Ｃ_1-3アルコキシカルボニル基又はＣ_6-10アリールカルボニル基であり、
Ｚ^1-1がＣ_1-3アルキル基であり、
Ｚ^2-1-1がＣ_1-3アルキル基であり、
Ｚ^2-1-2が水素原子又はＣ_1-3アルキル基であるピリダジノン化合物。
一般式（Ｉ−１）において、Ｒ^2-1が水素原子、メチル基又はエチル基であり、Ｇ¹が水素原子、アセチル基、プロピオニル基、メトキシカルボニル基、エトキシカルボニル基又はベンゾイル基であり、
Ｚ^1-1がメチル基又はエチル基であり、
Ｚ^2-1-1がメチル基又はエチル基であり、
Ｚ^2-1-2が水素原子、メチル基又はエチル基であるピリダジノン化合物。
一般式（Ｉ−２）

において、Ｒ^2-2が水素原子又はＣ_1-3アルキル基であり、Ｇ²が水素原子、ハロゲン原子で置換されていてもよいＣ_1-3アルキルカルボニル基又はＣ_1-3アルコキシカルボニル基であり、
Ｚ^2-2-1が水素原子又はＣ_1-3アルキル基であり、
Ｚ^2-2-2が水素原子又はＣ_1-3アルキル基であるピリダジノン化合物。
一般式（Ｉ−２）において、Ｒ^2-2が水素原子、メチル基又はエチル基であり、Ｇ²が水素原子、アセチル基、メトキシカルボニル基又はエトキシカルボニル基であり、
Ｚ^2-2-1が水素原子、メチル基又はエチル基であり、
Ｚ^2-2-2が水素原子、メチル基又はエチル基であるピリダジノン化合物。 In the general formula (I), R ¹ is a C _1-3 alkyl group or a (C _1-3 alkyloxy) C _1-3 alkyl group, R ² is a hydrogen atom or a methyl group,
When n represents an integer of 0, 1 or 2, and n represents 2, two Z ² may be the same or different. When n represents 1 or 2, the bonding position of Z ² is on the benzene ring. 4th and / or 6th
Z ¹ is a C _1-6 alkyl group (more preferably a C _1-3 alkyl group),
A pyridazinone compound in which Z ² is a C _1-6 alkyl group (more preferably a C _1-3 alkyl group).
In the general formula (I), R ¹ is a C _1-3 alkyl group or a (C _1-3 alkyloxy) C _1-3 alkyl group, R ² is a hydrogen atom or a methyl group, and G is a hydrogen atom or Following formula

{Wherein, R ^3b , R ^4b , R ^5b and R ^6b represent the same meaning as described above. }
Any of the groups represented by
When n represents an integer of 0, 1 or 2, and n represents 2, two Z ² may be the same or different. When n represents 1 or 2, the bonding position of Z ² is on the benzene ring. 4th and / or 6th
Z ¹ is a C _1-6 alkyl group (more preferably a C _1-3 alkyl group),
A pyridazinone compound in which Z ² is a C _1-6 alkyl group (more preferably a C _1-3 alkyl group).
In the general formula (I), R ¹ is a C _1-3 alkyl group or a (C _1-3 alkyloxy) C _1-3 alkyl group, R ² is a hydrogen atom or a methyl group, and G is a hydrogen atom or Following formula

{Wherein R ^3a and R ^4a represent the same meaning as described above. }
Any of the groups represented by
When n represents an integer of 0, 1 or 2, and n represents 2, two Z ² may be the same or different. When n represents 1 or 2, the bonding position of Z ² is on the benzene ring. 4th and / or 6th
Z ¹ is a C _1-6 alkyl group (more preferably a C _1-3 alkyl group),
A pyridazinone compound in which Z ² is a C _1-6 alkyl group (more preferably a C _1-3 alkyl group).
Formula (I-1)

In, R ^2-1 is a hydrogen atom or a C _1-3 alkyl group, G ¹ is hydrogen atom, a halogen atom with optionally substituted C _1-3 also be alkylcarbonyl group, C _1-3 alkoxycarbonyl group or A C _6-10 arylcarbonyl group,
Z ^1-1 is a C _1-3 alkyl group,
Z ^2-1-1 is a C _1-3 alkyl group,
A pyridazinone compound in which Z ^2-1-2 is a hydrogen atom or a C _1-3 alkyl group.
In the general formula (I-1), R ^2-1 is a hydrogen atom, a methyl group or an ethyl group, G ¹ is a hydrogen atom, an acetyl group, a propionyl group, a methoxycarbonyl group, an ethoxycarbonyl group or a benzoyl group,
Z ^1-1 is a methyl group or an ethyl group,
Z ^2-1-1 is a methyl group or an ethyl group,
A pyridazinone compound in which Z ^2-1-2 is a hydrogen atom, a methyl group or an ethyl group.
Formula (I-2)

In, R ^2-2 is hydrogen atom or a C _1-3 alkyl group, G ² is a hydrogen atom, a halogen atom substituted optionally C _1-3 also be alkylcarbonyl group or a C _1-3 alkoxycarbonyl group Yes,
Z ^2-2-1 is a hydrogen atom or a C _1-3 alkyl group,
A pyridazinone compound in which Z ^2-2-2 is a hydrogen atom or a C _1-3 alkyl group.
In the general formula (I-2), R ^2-2 is a hydrogen atom, a methyl group or an ethyl group, G ² is a hydrogen atom, an acetyl group, a methoxycarbonyl group or ethoxycarbonyl group,
Z ^2-2-1 is a hydrogen atom, a methyl group or an ethyl group,
A pyridazinone compound in which Z ^2-2-2 is a hydrogen atom, a methyl group or an ethyl group.

The compound of the present invention has an excellent weed control effect and can be used as an active ingredient of a herbicide. And some have excellent selectivity between crops and weeds. Examples of the weeds that can be controlled by the compound of the present invention include the following.
Bark, Oshiba, Enokorogusa, Akinoenokorogusa, Kinenokoro, Inobie, Okisakubi, Meriken-nikuki, Seban-sorghum, Shutter cane, Dermatophyllus, Oats, Rats, Blackgrass, Horsegrass, Bamboo Yellow-headed geese, Blue-headed dragonfly, Green-billed wing, Ichibibi, Akaza, Inuta, Red-tailed dogwood, American stag beetle, White-winged dipper, Blue-billed moth, Red-breasted moth, Egusa, Ragweed, Azalea, Yamgra, Red-tailed geese, Red-tailed geese Coniferous weeds such as convolvulus and sagebrush, Tainubie, Himetinubibie, Tama Filet, Kogomegatsuri, Hiderico, Matsubai, Inuhotarui, Taiwan Yamai, Mizugayatsuri, Kurogwaii, Kokiyagara, Shizui, Konagi, Azena, Abnomome, Kakishigusa, Himesohagi, Mizohakobe, Chirota Paddy field weeds such as Takasaburo, Ibokusa, Kishuussumenohee, Ezonosayayanukagusa.

  When the compound of the present invention is used as an active ingredient of a herbicide, the compound of the present invention is generally dissolved or dispersed in a suitable liquid carrier, or mixed or adsorbed with a suitable solid carrier, which is convenient for the intended use. It is formulated into a shape and used. Herbicides containing the compound of the present invention as an active ingredient include, for example, emulsions, solutions, oils, sprays, wettable powders, powders, DL (driftless) powders, granules, fine granules, fine granules F, fine granules It is a preparation in the form of F, granule wettable powder, aqueous solvent, flowable agent, dry flowable agent, jumbo agent, tablet, paste agent and the like. If necessary, these preparations may further contain formulation adjuvants such as emulsifiers, dispersants, spreading agents, penetrants, wetting agents, binders, thickeners, preservatives, antioxidants, and coloring agents. And can be prepared by known methods.

  Examples of the liquid carrier used for formulation include water, alcohols (eg, methanol, ethanol, 1-propanol, 2-propanol, ethylene glycol, etc.), ketones (eg, acetone, methyl ethyl ketone, etc.), Ethers (eg, dioxane, tetrahydrofuran, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether), aliphatic hydrocarbons (eg, hexane, octane, cyclohexane, kerosene, fuel oil, machine oil, etc.), aroma Group hydrocarbons (eg, benzene, toluene, xylene, solvent naphtha, methylnaphthalene, etc.), halogenated hydrocarbons (eg, dichloromethane, chloroform, carbon tetrachloride, etc.), acid amides (eg, Methylformamide, dimethylacetamide, N- methylpyrrolidone), esters (e.g., ethyl acetate, butyl acetate, fatty acid glycerin ester, etc.), nitriles (e.g., acetonitrile, and propionitrile, etc.) and the like. Two or more of these liquid carriers can be mixed and used in an appropriate ratio.

Solid carriers used for formulation include vegetable powders (for example, soybean powder, tobacco powder, wheat flour, wood powder, etc.), mineral powders (for example, kaolin, bentonite, acid clay, clays such as clay) Talc such as talc powder and wax stone powder, silica such as diatomaceous earth and mica powder), alumina, sulfur powder, activated carbon, saccharides (eg lactose, glucose etc.), inorganic salts (eg calcium carbonate, sodium bicarbonate) Etc.), hollow glass bodies (obtained by firing natural glass and enclosing bubbles therein), and the like. Two or more kinds of these solid carriers can be mixed and used at an appropriate ratio.
The liquid carrier or solid carrier is generally used in an amount of 1 to 99% by weight, preferably about 10 to 99% by weight, based on the entire preparation.

  A surfactant is usually used as an emulsifier, a dispersant, a spreading agent, a penetrating agent, a wetting agent and the like used for formulation. Examples of the surfactant include anions such as alkyl sulfate ester salt, alkyl aryl sulfonate salt, dialkyl sulfo succinate salt, polyoxyethylene alkyl aryl ether phosphate ester salt, lignin sulfonate salt, naphthalene sulfonate formaldehyde polycondensate. Nonionic surfactants such as surfactants and polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, polyoxyethylene alkyl polyoxypropylene block copolymers, sorbitan fatty acid esters and the like can be mentioned. Two or more kinds of these surfactants can be used. The surfactant is usually used in a proportion of 0.1 to 50% by weight, preferably about 0.1 to 25% by weight, based on the whole preparation.

  Examples of the binder and thickener include dextrin, sodium salt of carboxymethyl cellulose, polycarboxylic acid polymer compound, polyvinyl pyrrolidone, polyvinyl alcohol, sodium lignin sulfonate, calcium lignin sulfonate, sodium polyacrylate, gum arabic Sodium alginate, mannitol, sorbitol, bentonite minerals, polyacrylic acid and its derivatives, sodium salt of carboxymethyl cellulose, white carbon, natural sugar derivatives (for example, xanthan gum, guar gum, etc.), and the like.

  The content ratio of the compound of the present invention in the preparation is usually 1 to 90% by weight in emulsions, wettable powders, granule wettable powders, liquids, aqueous solvents, flowables, etc., and oils, powders, DL type powders In general, the ratio is 0.01 to 10% by weight, and in the case of fine granules, fine granules F, fine granules F, granules, etc., the ratio is usually 0.05 to 10% by weight. May change these concentrations as appropriate. Emulsions, wettable powders, granular wettable powders, liquids, aqueous solvents, flowables, etc. are usually used by appropriately diluting with water, etc., but usually diluted about 100 to 100,000 times. .

As a method for applying a herbicide containing the compound of the present invention as an active ingredient, the same methods as those used for usual well-known pesticides can be used, and examples include aerial spraying, soil spraying, and foliage spraying.
The amount used when the herbicide containing the compound of the present invention as an active ingredient is used as a herbicide for upland fields or paddy fields varies depending on the application area, application time, application method, target grass species, cultivated crops, etc. Is about 1 to 5000 g, preferably about 10 to 1000 g, per hectare of field or paddy field as the compound of the present invention.
The herbicide containing the compound of the present invention as an active ingredient is usually used as a pre-emergence soil admixture treatment agent, a pre-emergence soil treatment agent, or a post-emergence foliar treatment agent for controlling field weeds. For paddy field weed control, it is usually used as a pre-emergence soil treatment agent or a foliage and soil treatment agent.

The herbicide containing the compound of the present invention as an active ingredient may be one or more other herbicides, plant growth regulators, fungicides, insecticides, acaricides, nematicides, etc., if necessary It can be applied at the same time, and contains one or more other herbicides, plant growth regulators, fungicides, insecticides, acaricides, nematicides, etc. Can also be used.
As an active ingredient of other herbicides that can be applied and / or mixed with the compound of the present invention and used, for example,
(1) Phenoxy fatty acid herbicidal compound [2,4-PA, MCP, MCPB, phenothiol, mecoprop, fluroxypyr, triclopyr, clomeprop, naploanilide etc],
(2) Benzoic acid herbicidal compounds [2,3,6-TBA, dicamba, clopyralid, picloram, aminopyralid, quinclorac, quinmerac, etc. ],
(3) Urea herbicidal compounds [diuron, linuron, chlortoluron, isoproturon, fluometuron, isouron, tebuthiuron, tebuthiuron, tebuthiuron methabenzthiazuron, cumyluron, diimuron, methyl-daimuron, etc.],
(4) Triazine herbicidal compounds [atrazine, ametrine, cyanazine, simazine, propazine, simetrin, dimethmethrin] (Metribuzin), triaziflam etc.],
(5) Bipyridinium-based herbicidal compounds [paraquat, diquat, etc.]
(6) Hydroxybenzonitrile-based herbicidal compounds [bromoxynil, ioxynil, etc.],
(7) Dinitroaniline herbicidal compound [pendimethalin, prodiamine, trifluralin, etc.],
(8) Organophosphorus herbicidal compounds [amiprofos-methyl, butamifos, bensulide, piperophos, anilofos, glyphosate, glyphosate Vialaphos, etc.],
(9) Carbamate-based herbicidal compounds [dialate (tri-allate), tri-allate (EPTC), butyrate (bentilate), beniocarb, esprocarb, molinate, dimepiperate , Swep, chlorpropham, phenmedifam, phenisopham, pyributicalcarb, ashram, etc.],
(10) Acid amide-based herbicidal compounds [propanil, propyzamide, bromobutide, etobenzanide, etc.]
(11) Chloroacetanilide-based herbicidal compounds [acetochlor, alachlor, butachlor, dimethenamide, propachlor, metazachlor, tolachlor Pretilachlor, tenyl chlor (theny1ch1or), petoxamide, etc.],
(12) Diphenyl ether-based herbicidal compounds [acifluorfen-sodium, bifenox, oxyfluorfen, lactofen, fomesafen, clomethoxyn1, clomethoxyn1, etc. ,
(13) Cyclic imide-based herbicidal compounds [oxadiazon, cinidon-ethyl, carfentrazone-ethyl, sulfentrazone, flumicrolac-pentyl , Flumioxazin, pyraflufen-ethyl, oxadiargyl (1), pentoxazone, fluthiacet-methyl, butafenzilfen (butafenzilfen) ,
(14) Pyrazole-based herbicidal compounds [benzofenap, pyrazolate, pyrazoxifene, topramzone, pyrasulfotole, etc.]
(15) Triketone-based herbicidal compounds [isoxaflutole, benzobicyclon, sulcotrione, mesotrione, tembotrione, tefuryltrione, etc.
(16) Aryloxyphenoxypropionic acid herbicidal compounds [clodinahop-propargyl, cyhalofop-butyl, diclohop-methyl, phenoxaprop-ethyl ), Fluazifop-butyl, haloxyhop-methyl, quizalofop-ethyl, metamihop, etc.],
(17) Trione oxime-based herbicidal compounds [aloxydim-sodium, cetoxydim, butroxydim, crestodim, cloproxidim, cycloxidimy] , Tralcoxydim, profoxydim, etc.],
(18) Sulfonylurea-based herbicidal compounds [chlorsulfuron, sulfomethuron-methyl, metsulfuron-methyl, chlorimuron-ethyl, tribenuron Methyl (tribenuron-methyl), trisulfuron (triasulfuron), bensulfuron-methyl (bensulfuron-methyl), thifensulfuron-methyl (pyrazosulfuron-methyl), pyrazosulfuron-methyl (pril) sulfuron-methyl) ), Nicosulfuron (ni) osulfuron, amidosulfuron, cynosulfuron, imazosulfuron, rimsulfuron, halosulfuron (thulfuron methyl), sulfuluron (thulfuron) , Triflusulfuron-methyl, flazasulfuron, cyclosulfamuron, flupirsulfuron, sulfosulfuron, azisulfuron Sulfulon, ethoxysulfuron, oxasulfuron, iodosulfuron-methyl-sodium, foramsulfuron, mesosulfuron, mesosulfuron Cisulfuron, tritosulfuron, orthosulfamuron, flucetosulfuron, etc.],
(19) Imidazolinone-type herbicidal compounds [imazametabenzmethyl (imazamethabenz-methyl), imazametapyr, imazapyr (imazapyr), imazapir (imazapyr)
(20) Sulfonamide-based herbicidal compounds [flumetslam, metosulam, dicloslam, floraslam, chloransrammethyl, penoxsulx, penoxsulx, etc. ],
(21) Pyrimidinyloxybenzoic acid-based herbicidal compounds [pyrithiobac-sodium, bispyribac-sodium, pyriminobac-methyl1], pyribenzoxifimpyri ), Pyrimisulfan etc.],
(22) Other strains of herbicidal compounds [bentazones, bromacil, terbacil, chlorthiamid, isoxaben, dinoseb, amitrole, inmethyline] , Tridiphane, dalapon (da1apon), diflufenzopyr sodium (diflufenzopyr-sodium), dithiopyr (dithiopyr), thiazopyr (thiazopyr), sodium flucarbazone, flucarbazone , Mefenacet, flufenacet, fentrazamide, caffentrol, indanophan, oxaziclomefone, benfrate, benfrate Norflurazon, flurtamone, diflufenican, picolinafene, beflubutamid, clomazone, amicarbazone one), pinoxaden (pinoxaden), pyraclonil (pyraclonil), pyroxasulfone (pyroxasulfone), thien-carbazone methyl (thiencarbazone-methyl), etc.] and the like,
As an active ingredient of a plant growth regulator, for example, hymexazole (hymexazole), paclobutrazole (paclobutrazol), uniconazole-P (uniconazole-P), inabenfide (inabenfide), prohexadione calcium (prohexadione-calcium) and the like. Named,
As an active ingredient of a disinfectant, for example,
(1) Polyhaloalkylthio-based bactericidal compound [captan etc.],
(2) Organophosphorus-based bactericidal compound [IBP, EDDP, tolcrofos-methyl, etc.],
(3) Benzimidazole-type bactericidal compounds [benomyl, carbendazim, thiophanate-methyl, etc.],
(4) Carboxamide-based fungicidal compounds [carboxin, mepronil, flutolanil, thifluzamide, furamethpyr, boscalid, penthioprad, penthiopy, etc.
(5) Dicarboximide fungicidal compounds [procymidone, iprodione, vinclozolin, etc.],
(6) Acylalanine-based bactericidal compound [metalaxyl etc.],
(7) Azolic fungicidal compounds [triadimefon, triadimenol, propiconazole, tebuconazole, cyproconazole, epoxiconazole, epoxiconazole Oconazole, ipconazole, triflumizole, prochloraz, etc.],
(8) Morpholine-based bactericidal compounds [dodemorph, tridemorph, fenpropimorph, etc.]
(9) Strobilurin-based bactericidal compounds [azoxystrobin, cresoxime-methyl, methinostrobin, trifloxystrobin, picoxystrobin, picoxystrobin (Pyraclostrobin) etc.],
(10) Antibacterial fungicidal compounds [validamycin A, blastcidin S, kasugamycin, polyoxin, etc.]
(11) Dithiocarbamate fungicidal compound [mancozeb, maneb, etc.]
(12) Other bactericidal compounds [fthalide, probenazole, isoprothiolane, tricyclazole, pyroquilon, ferrimzone, prosylone] (Carpropamid), diclocymet, phenoxanil, thiazinyl, dicromezine, teclophthalam, pencycuron, oloxinic acid (x), oxolinic acid (x) Trifoline, fenpropidin, spiroxamine, fluazinam, iminooctadine, fenpiclonil, fludioxonimide, fludioxonimide ), Silthiofam, proquinazide, cyflufenamide, basic copper calcium sulfate, etc.]
As an active ingredient of an insecticide, for example,
(1) Organophosphorus insecticidal compounds [fenthion, fenitrothion, pirimiphos-methyl, diazinon, quinalphos, isoxathion, pyridafenthiol chlorpyrifos-methyl), bamidithion, malathion, phentoate, dimethoate, disulfoton, monocrotophos, tetrachlorphos rvinphos), chlorfenvinphos (chlorfenvinphos), propaphos (propaphos), acephate (acephate), trichlorfon (trichlorphon), EPN, pyraclofos (pyraclofos), etc.],
(2) Carbamate-based insecticidal compounds [carbaryl, metolcarb, isoprocarb, BPMC, propoxur, XMC, carbofuran, carbsulfan, carbsulfan, Furathiocarb, mesomyl, thiodicarb, etc.],
(3) Synthetic pyrethroid insecticidal compounds [tefluthrin, bifenthrin, cycloprothrin, etofenprox, etc.]
(4) Nereistoxin insecticidal compound [cartap, bensultap, thiocyclam, etc.],
(5) Neonicotinoid insecticidal compounds [imidacloprid, nitenpyram, acetamiprid, thiamethoxam, thiacloanid, dinotefurin, ditethofurin
(6) Benzoylphenylurea insecticide [chlorfluazuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, etc.]
(7) Macrolide insecticidal compounds [emamectin, spinosad, etc.]
(8) Other insecticidal compounds [buprofezin, tebufenozide, fipronil, etiprole, pymetrozine, diafenthiaurdone, diafenthiurb (Tolfenpyrad), pyridalyl (pyridalyl), flonicamid (flonicamid), fulvendiamide (flubenamide) and the like], etc.
Examples of active ingredients of the acaricide include hexythiazox, pyridaben, fenpyroximate, tebufenpyrad, chlorfenapyr, oxafenizole , Bifenazate, spirodiclofen and the like,
Examples of the active ingredient of the nematicide include fostiazate and kazusafos.

  The herbicides containing the compound of the present invention as an active ingredient further include safeners (for example, furilazole, dichlormid, benoxacor, alidochlor, isoxadifen-ethyl). ), Fenchlorazole-ethyl, mefenpyr-diethyl, cloquintocet-mexyl, fenchlorim, cyprosulfamide, cyprosulfamide. , Oxabetrilin, fluxo Enimu (Fluxofenim), flurazole (Flurazole), 1,8-naphthalic anhydride (l, 8-naphthalic anhydride) and the like), dyes, fertilizers (e.g., may be appropriately mixed urea, etc.) and the like.

The compound of the present invention can be used as a herbicide for agricultural land such as fields, paddy fields, lawns, orchards, or non-agricultural land. The compound of the present invention may be able to control weeds in the cultivated land without causing phytotoxicity in the cultivated land or the like where the “crop” or the like listed below is cultivated.
Agricultural crops: corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, buckwheat, sugar beet, rapeseed, sunflower, sugar cane, tobacco, etc.
Vegetables: Eggplant vegetables (eggplants, tomatoes, peppers, peppers, potatoes, etc.), cucurbits vegetables (cucumbers, pumpkins, zucchini, watermelons, melons, etc.), cruciferous vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage) , Mustard, broccoli, cauliflower, etc.), asteraceae vegetables (burdock, shungiku, artichoke, lettuce, etc.), liliaceae vegetables (eg, leek, onion, garlic, asparagus, etc.), celeryaceae vegetables (carrot, parsley, celery, American redfish) Etc.), red crustacean vegetables (spinach, chard, etc.), persimmon vegetables (perilla, mint, basil, etc.), strawberries, sweet potatoes, yam, taro, etc.
Bridegroom,
Foliage plant,
Fruit trees: apples, pears, Japanese pears, quince, quince, etc., nuclear fruits (peaches, plums, nectarines, ume, 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, etc.
Trees other than fruit trees; tea, mulberry, flowering trees, street trees (ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple, oak, poplar, redwood, fu, sycamore, zelkova, black bean, fir tree, Tsuga, rat, pine, Spruce, yew) etc.

The above "crop" includes HPPD inhibitors such as isoxaflutol, ALS inhibitors such as imazetapyr and thifensulfuron methyl, EPSP synthase inhibitors, glutamine synthase inhibitors, acetyl CoA carboxylase inhibitors, bromoxynil, etc. Also included are crops to which tolerance to herbicides has been imparted by classical breeding methods or genetic engineering techniques.
“Crops” to which tolerance has been imparted by a classic breeding method include, for example, imidazolinone-based herbicide-resistant Clearfield (registered trademark) canola, sulfonylurea-based ALS such as thifensulfuron-methyl, etc. Inhibiting herbicide resistant STS soybeans. Similarly, SR corn and the like are examples of crops to which tolerance has been imparted to acetyl CoA carboxylase inhibitors such as trione oxime and aryloxyphenoxypropionic acid herbicides by classical breeding methods. Crops that have been rendered tolerant to acetyl CoA carboxylase inhibitors are Procedures of the National Academy of Sciences of the United States of America (Proc. Natl. Acad. Sci. USA) 87, 7175-7179 (1990). A mutant acetyl CoA carboxylase resistant to an acetyl CoA carboxylase inhibitor has been reported in Weed Science 53, 728-746 (2005), and the like. By introducing a mutation related to imparting resistance into a crop acetyl-CoA carboxylase, a crop resistant to the acetyl-CoA carboxylase inhibitor can be produced.

  Examples of the “crop” to which tolerance has been imparted by gene recombination techniques include glyphosate and glufosinate-resistant corn varieties such as Roundup Ready (registered trademark) and Liberty Link (registered trademark). Is already sold under the brand name.

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

  In addition, genetically modified plants that contain one or more insecticidal pest resistance genes and express one or more toxins are already known, and some are commercially available. Examples of these genetically modified plants include Yieldgard (registered trademark) (a corn variety that expresses Cry1Ab toxin), YieldGuard Rootworm (registered trademark) (a corn variety that expresses Cry3Bb1 toxin), YieldGuard Plus (registered trademark) (a corn variety expressing Cry1Ab and Cry3Bb1 toxin), Herculex I (registered trademark) (phosphino for conferring resistance to Cry1Fa2 toxin and glufosinate Corn varieties expressing Tricine N-acetyltransferase (PAT)), NuCOTN33B [registered trademark] (cotton varieties expressing Cry1Ac toxin), Volgaard I (Bollgard I) (registered trademark) (cotton variety expressing Cry1Ac toxin), Volgard II (Bollgard II) (registered trademark) (cotton variety expressing Cry1Ac and Cry2Ab toxin), VIPCOT (registered trademark) (expressing VIP toxin) Cotton Leaf), New Leaf (registered trademark) (potato variety expressing Cry3A toxin), Natureguard Agurisure GT Advantage (Nature Gard (registered trademark) GT Advantage (GT21 glyphosate resistant trait)) , Agurisure CB Advantage (Agriure® CB Advantage) (Bt11 corn borer (CB) trait), Protector (Register) Target], and the like.

The “crop” includes those that have been given the ability to produce an anti-pathogenic substance having a selective action using genetic recombination technology.
Examples of anti-pathogenic substances include PR proteins (described in PRPs, EP-A-0392225); sodium channel inhibitors, calcium channel inhibitors (virus-produced KP1, KP4, KP6 toxins, etc.) Stilbene synthase; bibenzyl synthase; chitinase; glucanase; peptide antibiotics, heterocyclic antibiotics, protein factors involved in plant disease resistance (called plant disease resistance genes) , Described in WO03 / 000906), and the like. Such anti-pathogenic substances and genetically modified plants that produce them are described in EP-A-0392225, WO95 / 33818, EP-A-0353191, and the like.

When the compound of the present invention is mixed with flumioxazin, the mixing ratio is preferably in the range of 1: 0.1 to 1:10. The mixture of the compound of the present invention and flumioxazin can be applied before germination (soil treatment) or after germination (foliage treatment). The mixture causes phytotoxicity to crops such as corn, rice, wheat, barley, rye, oats, sorghum, cotton, soybeans, peanuts, sugar beet, rapeseed, sunflower, and sugarcane. In some cases, weeds in the farmland can be controlled. The mixture may also be used in cultivated land such as lawn, orchard or non-cultivated land.
In addition, when the compound of the present invention is mixed with glyphosate, the mixing ratio is preferably in the range of 1: 1 to 1: 100. The mixture of the compound of the present invention and glyphosate can be applied after germination (foliage treatment). The mixture causes phytotoxicity to crops such as corn, rice, wheat, barley, rye, oats, sorghum, cotton, soybeans, peanuts, sugar beet, rapeseed, sunflower, and sugarcane. In some cases, weeds in the farmland can be controlled. The mixture may also be used in cultivated land such as lawn, orchard or non-cultivated land.
The compounds of the present invention and the mixtures are suitable as herbicides for use in upland fields.

〔式中、Ｒ⁷はＣ_1-6アルキル基（例えば、メチル基、エチル基等）を表し、Ｒ¹、Ｒ²、Ｚ¹、Ｚ²及びｎは前記と同じ意味を表す。〕
本反応は通常溶媒中で行なう。使用できる溶媒としては、例えば、水；テトラヒドロフラン、ジオキサン等のエーテル系溶媒、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金属水酸化物としては、例えば、水酸化ナトリウム、水酸化カリウム等のアルカリ金属の水酸化物等が挙げられる。本反応に用いられる金属水酸化物の使用量は、一般式（II）で示される化合物に対して、通常１〜１２０モル当量、好ましくは１〜４０モル当量である。
本反応の反応温度は、通常室温から使用する溶媒の沸点の範囲であり、好ましくは溶媒の沸点である。なお本反応は封管又は耐圧密閉容器中で加熱して行なうこともできる。本反応の反応時間は、通常５分〜数週間程度である。
本反応の終了は、反応混合物の一部をサンプリングして、薄層クロマトグラフィー、高速液体クロマトグラフィー等の分析手段により確認することができる。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、濃縮する等の操作を行うことにより、一般式（I−ａ）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
Among the compounds of the present invention, the compound represented by the general formula (Ia), in which G is a hydrogen atom, can be produced by reacting the compound represented by the general formula (II) with a metal hydroxide. .

[Wherein, R ⁷ represents a C _1-6 alkyl group (for example, methyl group, ethyl group, etc.), and R ¹ , R ² , Z ¹ , Z ² and n represent the same meaning as described above. ]
This reaction is usually carried out in a solvent. Examples of the solvent that can be used include water; ether solvents such as tetrahydrofuran and dioxane, and mixed solvents thereof.
Examples of the metal hydroxide used in this reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide. The usage-amount of the metal hydroxide used for this reaction is 1-120 molar equivalent normally with respect to the compound shown by general formula (II), Preferably it is 1-40 molar equivalent.
The reaction temperature of this reaction is usually in the range from room temperature to the boiling point of the solvent used, preferably the boiling point of the solvent. This reaction can also be carried out by heating in a sealed tube or a pressure-resistant sealed container. The reaction time for this reaction is usually about 5 minutes to several weeks.
The completion of this reaction can be confirmed by sampling a part of the reaction mixture and analyzing means such as thin layer chromatography or high performance liquid chromatography. After completion of this reaction, for example, by adding an acid to the reaction mixture to neutralize it, mixing with water, extracting with an organic solvent, and drying and concentrating the obtained organic layer, The compound represented by the formula (Ia) can be isolated.

〔式中、Ｇ³はＧの定義のうち水素原子以外の基を表し、Ｘはハロゲン原子（例えば、塩素原子、臭素原子、ヨウ素原子等）又は式ＯＧ³で表される基を表し、Ｒ¹、Ｒ²、Ｚ¹、Ｚ²及びｎは前記と同じ意味を表す。〕
本反応は溶媒中で行なうことができる。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；ジエチルエーテル、ジイソプロピルエーテル、ジオキサン、テトラヒドロフラン、ジメトキシエタン等のエーテル類；ジクロロメタン、クロロホルム、１，２−ジクロロエタン等のハロゲン化炭化水素類；ジメチルホルムアミド、ジメチルアセトアミド等のアミド類；ジメチルスルホキシド等のスルホキシド類；スルホラン等のスルホン類、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一般式（III）で示される化合物としては、例えば、塩化アセチル、塩化プロピオニル、塩化イソブチリル、塩化ピバロイル、塩化ベンゾイル、シクロヘキサンカルボン酸クロリド等のカルボン酸のハロゲン化物；無水酢酸、無水トリフルオロ酢酸等のカルボン酸の無水物；クロロギ酸メチル、クロロギ酸エチル、クロロギ酸フェニル等の炭酸半エステルのハロゲン化物；塩化ジメチルカルバモイル等のカルバミン酸のハロゲン化物；塩化メタンスルホニル、塩化ｐ−トルエンスルホニル等のスルホン酸のハロゲン化物；メタンスルホン酸無水物、トリフルオロメタンスルホン酸無水物等のスルホン酸の無水物；ジメチル クロロホスファート等のリン酸エステルのハロゲン化物等が挙げられる。本反応に用いられる一般式（III）で示される化合物の使用量は、一般式（Ｉ−ａ）で示される化合物に対して、通常１モル当量以上、好ましくは１〜３モル当量である。
本反応は通常、塩基の存在下に行なう。本反応において用いられる塩基としては、例えば、トリエチルアミン、トリプロピルアミン、ピリジン、ジメチルアミノピリジン、１，８−ジアザビシクロ［５．４．０］−７−ウンデセン等の有機塩基；水酸化ナトリウム、水酸化カリウム、水酸化カルシウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸カルシウム、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塩基の使用量は、一般式（Ｉ−ａ）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−１０〜５０℃である。本反応の反応時間は通常、１０分〜３０時間である。
本反応の終了は、反応混合物の一部をサンプリングして、薄層クロマトグラフィー、高速液体クロマトグラフィー等の分析手段により確認することができる。本反応の終了後、例えば反応混合物と水とを混合し、有機溶媒にて抽出し、得られた有機層を乾燥、濃縮する等の操作を行うことにより、一般式（Ｉ−ｂ）で示される化合物を単離することができる。
一般式（III）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。 Manufacturing method 2
Among the compounds of the present invention, G is a group other than a hydrogen atom, and the compound represented by the general formula (Ib) is selected from the compound represented by the general formula (Ia) and the compound represented by the general formula (III). Can be manufactured.

[In the formula, G ³ represents a group other than a hydrogen atom in the definition of G, X represents a halogen atom (for example, a chlorine atom, a bromine atom, an iodine atom, etc.) or a group represented by the formula OG ³ ; ¹ , R ² , Z ¹ , Z ² and n represent the same meaning as described above. ]
This reaction can be carried out in a solvent. Examples of the solvent that can be used include aromatic hydrocarbons such as benzene and toluene; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, and dimethoxyethane; halogenated carbonization such as dichloromethane, chloroform, 1,2-dichloroethane, and the like. Examples thereof include hydrogens; amides such as dimethylformamide and dimethylacetamide; sulfoxides such as dimethyl sulfoxide; sulfones such as sulfolane, and mixed solvents thereof.
Examples of the compound represented by the general formula (III) used in this reaction include halides of carboxylic acids such as acetyl chloride, propionyl chloride, isobutyryl chloride, pivaloyl chloride, benzoyl chloride, cyclohexanecarboxylic acid chloride; acetic anhydride, anhydrous Carboxylic acid anhydrides such as trifluoroacetic acid; halides of carbonic acid half esters such as methyl chloroformate, ethyl chloroformate and phenyl chloroformate; halides of carbamic acid such as dimethylcarbamoyl chloride; methanesulfonyl chloride, p-toluene chloride Examples thereof include halides of sulfonic acids such as sulfonyl; anhydrides of sulfonic acids such as methanesulfonic anhydride and trifluoromethanesulfonic anhydride; halides of phosphate esters such as dimethyl chlorophosphate. The usage-amount of the compound shown by general formula (III) used for this reaction is 1 molar equivalent or more normally with respect to the compound shown by general formula (Ia), Preferably it is 1-3 molar equivalent.
This reaction is usually performed in the presence of a base. Examples of the base used in this reaction include organic bases such as triethylamine, tripropylamine, pyridine, dimethylaminopyridine, 1,8-diazabicyclo [5.4.0] -7-undecene; sodium hydroxide, hydroxide Examples include inorganic bases such as potassium, calcium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, calcium carbonate, sodium hydride. The usage-amount of the base used for this reaction is 0.5-10 molar equivalent normally with respect to the compound shown by general formula (Ia), Preferably it is 1-5 molar equivalent.
The reaction temperature of this reaction is usually −30 to 180 ° C., preferably −10 to 50 ° C. The reaction time for this reaction is usually 10 minutes to 30 hours.
The completion of this reaction can be confirmed by sampling a part of the reaction mixture and analyzing means such as thin layer chromatography or high performance liquid chromatography. After the completion of this reaction, for example, the reaction mixture and water are mixed, extracted with an organic solvent, and the obtained organic layer is dried and concentrated to perform the operation represented by the general formula (Ib). The compound can be isolated.
The compound represented by the general formula (III) is a known compound or can be produced from a known compound.

〔式中、Ｒ⁹はＣ_1-6アルキル基（例えば、メチル基、エチル基等）を表し、Ｒ¹、Ｒ²、Ｚ¹、Ｚ²及びｎは前記と同じ意味を表す。〕
本反応は通常溶媒中で行なう。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、ジイソプロピルエーテル、ジオキサン、テトラヒドロフラン、ジメトキシエタン等のエーテル類；ジクロロメタン、クロロホルム、１，２−ジクロロエタン等のハロゲン化炭化水素類；ジメチルホルムアミド、ジメチルアセトアミド等のアミド類；スルホラン等のスルホン類、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、水素化ナトリウム等のアルカリ金属水素化物、トリエチルアミン、トリブチルアミン、Ｎ，Ｎ−ジイソプロピルエチルアミン等の有機塩基等が挙げられる。本反応に用いられる塩基の使用量は、一般式（VI）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２〜５モル当量である。
本反応の反応温度は通常−６０〜１８０℃、好ましくは−１０〜１００℃である。本反応の反応時間は通常１０分〜３０時間である。
本反応の終了は、反応混合物の一部をサンプリングして、薄層クロマトグラフィー、高速液体クロマトグラフィー等の分析手段により確認することができる。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、濃縮する等の操作を行うことにより、一般式（I−ａ）で示される化合物を単離することができる。 Production method 3
Among the compounds of the present invention, the compound represented by the general formula (Ia) in which G is a hydrogen atom can also be produced by the following production method. That is, the compound represented by general formula (Ia) can be produced by allowing a base to act on the compound represented by general formula (VI).

[Wherein R ⁹ represents a C _1-6 alkyl group (eg, methyl group, ethyl group, etc.), and R ¹ , R ² , Z ¹ , Z ² and n represent the same meaning as described above. ]
This reaction is usually carried out in a solvent. Examples of solvents that can be used include aromatic hydrocarbons such as benzene, toluene and xylene; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran and dimethoxyethane; halogens such as dichloromethane, chloroform and 1,2-dichloroethane. Hydrocarbons; amides such as dimethylformamide and dimethylacetamide; sulfones such as sulfolane, or a mixed solvent thereof.
Examples of the base used in this reaction include metal alkoxides such as potassium tert-butoxide, alkali metal hydrides such as sodium hydride, organic bases such as triethylamine, tributylamine and N, N-diisopropylethylamine. The usage-amount of the base used for this reaction is 1-10 molar equivalent normally with respect to the compound shown by general formula (VI), Preferably it is 2-5 molar equivalent.
The reaction temperature of this reaction is usually −60 to 180 ° C., preferably −10 to 100 ° C. The reaction time for this reaction is usually 10 minutes to 30 hours.
The completion of this reaction can be confirmed by sampling a part of the reaction mixture and analyzing means such as thin layer chromatography or high performance liquid chromatography. After completion of this reaction, for example, by adding an acid to the reaction mixture to neutralize it, mixing with water, extracting with an organic solvent, and drying and concentrating the obtained organic layer, The compound represented by the formula (Ia) can be isolated.

〔式中、Ｘ¹は脱離基（例えば、塩素原子、臭素原子、ヨウ素原子等のハロゲン原子等）を表し、Ｘ²はハロゲン原子（例えば、塩素原子、臭素原子、ヨウ素原子等）を表し、Ｒ⁸はＣ_1-6アルキル基（例えば、メチル基、ブチル基等）を表し、Ｒ¹、Ｒ²、Ｒ⁷、Ｚ¹、Ｚ²及びｎは前記と同じ意味を表す。〕
本反応においては、一般式（IV）で示される化合物を、一般式（Ｖ−ａ）、（Ｖ−ｂ）又は（Ｖ−ｃ）で示される有機金属試薬（通常、一般式（IV）で示される化合物に対して１モル当量以上、好ましくは１〜３モル当量）とカップリング反応させることにより、一般式（II）で示される化合物を製造することができる。
一般式（Ｖ−ａ）で示される化合物を用いる反応は、溶媒中で行なう。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、ジイソプロピルエーテル、ジオキサン、テトラヒドロフラン、ジメトキシエタン等のエーテル類；アセトン、メチルエチルケトン等のケトン類；ジメチルホルムアミド、ジメチルアセトアミド等のアミド類；ジメチルスルホキシド等のスルホキシド類；スルホラン等のスルホン類；水、又はこれらの混合溶媒が用いられる。
また、一般式（Ｖ−ａ）で示される化合物を用いる反応は、塩基の存在下に行なう。使用できる塩基としては、例えば、トリエチルアミン、トリプロピルアミン、ピリジン、ジメチルアニリン、ジメチルアミノピリジン、１，８−ジアザビシクロ［５．４．０］−７−ウンデセン等の有機塩基；水酸化ナトリウム、水酸化カリウム、水酸化カルシウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸カルシウム、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、一般式（IV）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。
更に、一般式（Ｖ−ａ）で示される化合物を用いる反応は、触媒の存在下に行なう。使用できる触媒としては、例えば、テトラキス（トリフェニルホスフィン）パラジウム、ジクロロビス（トリフェニルホスフィン）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、一般式（IV）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。また一般式（Ｖ−ａ）で示される化合物を用いる反応は、４級アンモニウム塩を添加することが好ましい。使用することのできる４級アンモニウム塩としては、例えば、臭化テトラブチルアンモニウム等が挙げられる。
一般式（Ｖ−ａ）で示される化合物を用いる反応の反応温度は、通常２０〜１８０℃、好ましくは６０〜１５０℃である。該反応の反応時間は通常３０分〜１００時間である。該反応の終了は、反応混合物の一部をサンプリングして、薄層クロマトグラフィー、高速液体クロマトグラフィー等の分析手段により確認することができる。該反応の終了後、例えば反応混合物と水とを混合し、有機溶媒にて抽出し、得られた有機層を乾燥、濃縮する等の操作を行うことにより、一般式（II）で示される化合物を単離することができる。
一般式（Ｖ−ｂ）で示される化合物を用いる反応は、溶媒中で行なう。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；ジエチルエーテル、ジイソプロピルエーテル、ジオキサン、テトラヒドロフラン、ジメトキシエタン等のエーテル類；又はこれらの混合溶媒が挙げられる。
一般式（Ｖ−ｂ）で示される化合物を用いる反応は、触媒の存在下に行なう。使用できる触媒としては、例えば、ジクロロビス（１，３−ジフェニルホスフィノ）プロパンニッケル、ジクロロビス（トリフェニルホスフィン）ニッケル等のニッケル触媒、テトラキス（トリフェニルホスフィン）パラジウム、ジクロロビス（トリフェニルホスフィン）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、一般式（IV）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。
一般式（Ｖ−ｂ）で示される化合物を用いる反応の反応温度は、通常−８０〜１８０℃、好ましくは−３０〜１５０℃である。該反応の反応時間は通常３０分〜１００時間である。該反応の終了は反応混合物の一部をサンプリングして、薄層クロマトグラフィー、高速液体クロマトグラフィー等の分析手段により確認することができる。該反応の終了後、例えば反応混合物と水とを混合し、有機溶媒にて抽出し、得られた有機層を乾燥、濃縮する等の操作を行うことにより、一般式（II）で示される化合物を単離することができる。
一般式（Ｖ−ｃ）で示される化合物を用いる反応は、溶媒中で行なう。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；ジエチルエーテル、ジイソプロピルエーテル、ジオキサン、テトラヒドロフラン、ジメトキシエタン等のエーテル類；クロロホルム、１，２−ジクロロエタン等のハロゲン化炭化水素類；ジメチルホルムアミド、ジメチルアセトアミド等のアミド類；又はこれらの混合溶媒が挙げられる。
一般式（Ｖ−ｃ）で示される化合物を用いる反応は、触媒の存在下に行なう。使用できる触媒としては、例えば、テトラキス（トリフェニルホスフィン）パラジウム、ジクロロビス（トリフェニルホスフィン）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、一般式（IV）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。
一般式（Ｖ−ｃ）で示される化合物を用いる反応の反応温度は、通常−８０〜１８０℃、好ましくは−３０〜１５０℃である。該反応の反応時間は通常３０分〜１００時間である。該反応の終了は反応混合物の一部をサンプリングして、薄層クロマトグラフィー、高速液体クロマトグラフィー等の分析手段により確認することができる。該反応の終了後、例えば反応混合物と水とを混合し、有機溶媒にて抽出し、得られた有機層を乾燥、濃縮する等の操作を行うことにより、一般式（II）で示される化合物を単離することができる。
一般式（II）で示される化合物は、例えばテトラへドロン（Ｔｅｔｒａｈｅｄｒｏｎ）、５７巻、１３２３〜１３３０頁（２００１年）等に記載されている方法に準じる方法に従い製造することができる。
一般式（Ｖ−ａ）、（Ｖ−ｂ）又は（Ｖ−ｃ）で示される有機金属試薬は公知の化合物であるか、あるいは公知の化合物から公知の方法に準じる方法に従い製造することができる。
一般式（IV）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 manufacturing method 1
The compound represented by the general formula (II) can be produced, for example, by the following production method.

[Wherein, X ¹ represents a leaving group (for example, a halogen atom such as chlorine atom, bromine atom, iodine atom, etc.), and X ² represents a halogen atom (for example, chlorine atom, bromine atom, iodine atom, etc.) , R ⁸ represents a C _1-6 alkyl group (for example, a methyl group, a butyl group, etc.), and R ¹ , R ² , R ⁷ , Z ¹ , Z ² and n represent the same meaning as described above. ]
In this reaction, the compound represented by the general formula (IV) is converted into an organometallic reagent represented by the general formula (Va), (Vb) or (Vc) (usually represented by the general formula (IV)). The compound represented by the general formula (II) can be produced by a coupling reaction with 1 mole equivalent or more, preferably 1 to 3 mole equivalent) of the compound shown.
The reaction using the compound represented by the general formula (Va) is carried out in a solvent. Examples of solvents that can be used include aromatic hydrocarbons such as benzene and toluene; alcohols such as methanol, ethanol, and propanol; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, and dimethoxyethane; acetone, methyl ethyl ketone, and the like. Ketones; amides such as dimethylformamide and dimethylacetamide; sulfoxides such as dimethyl sulfoxide; sulfones such as sulfolane; water or a mixed solvent thereof.
The reaction using the compound represented by the general formula (Va) is performed in the presence of a base. Examples of the base that can be used include organic bases such as triethylamine, tripropylamine, pyridine, dimethylaniline, dimethylaminopyridine, 1,8-diazabicyclo [5.4.0] -7-undecene; sodium hydroxide, hydroxide Inorganic bases such as potassium, calcium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, calcium carbonate, cesium carbonate, potassium phosphate and the like can be mentioned. The usage-amount of the base used is 0.5-10 molar equivalent normally with respect to the compound shown by general formula (IV), Preferably it is 1-5 molar equivalent.
Furthermore, the reaction using the compound represented by the general formula (Va) is carried out in the presence of a catalyst. Examples of the catalyst that can be used include palladium catalysts such as tetrakis (triphenylphosphine) palladium and dichlorobis (triphenylphosphine) palladium. The usage-amount of the catalyst used is 0.001-0.5 molar equivalent normally with respect to the compound shown by general formula (IV), Preferably it is 0.01-0.2 molar equivalent. In the reaction using the compound represented by the general formula (Va), it is preferable to add a quaternary ammonium salt. Examples of quaternary ammonium salts that can be used include tetrabutylammonium bromide.
The reaction temperature of the reaction using the compound represented by the general formula (Va) is usually 20 to 180 ° C, preferably 60 to 150 ° C. The reaction time is usually 30 minutes to 100 hours. The completion of the reaction can be confirmed by sampling a part of the reaction mixture and analyzing means such as thin layer chromatography or high performance liquid chromatography. After completion of the reaction, for example, the reaction mixture and water are mixed, extracted with an organic solvent, and the resulting organic layer is dried, concentrated, and the like, whereby the compound represented by the general formula (II) is obtained. Can be isolated.
The reaction using the compound represented by the general formula (Vb) is carried out in a solvent. Examples of the solvent that can be used include aromatic hydrocarbons such as benzene and toluene; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, and dimethoxyethane; or a mixed solvent thereof.
The reaction using the compound represented by the general formula (Vb) is carried out in the presence of a catalyst. Examples of the catalyst that can be used include nickel catalysts such as dichlorobis (1,3-diphenylphosphino) propane nickel and dichlorobis (triphenylphosphine) nickel, tetrakis (triphenylphosphine) palladium, dichlorobis (triphenylphosphine) palladium and the like. A palladium catalyst etc. are mentioned. The usage-amount of the catalyst used is 0.001-0.5 molar equivalent normally with respect to the compound shown by general formula (IV), Preferably it is 0.01-0.2 molar equivalent.
The reaction temperature of the reaction using the compound represented by the general formula (Vb) is usually −80 to 180 ° C., preferably −30 to 150 ° C. The reaction time is usually 30 minutes to 100 hours. Completion of the reaction can be confirmed by sampling a part of the reaction mixture and analyzing means such as thin layer chromatography or high performance liquid chromatography. After completion of the reaction, for example, the reaction mixture and water are mixed, extracted with an organic solvent, and the resulting organic layer is dried, concentrated, and the like, whereby the compound represented by the general formula (II) is obtained. Can be isolated.
The reaction using the compound represented by the general formula (Vc) is carried out in a solvent. Examples of solvents that can be used include aromatic hydrocarbons such as benzene and toluene; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, and dimethoxyethane; halogenated hydrocarbons such as chloroform and 1,2-dichloroethane. Amides such as dimethylformamide and dimethylacetamide; or a mixed solvent thereof.
The reaction using the compound represented by the general formula (Vc) is carried out in the presence of a catalyst. Examples of the catalyst that can be used include palladium catalysts such as tetrakis (triphenylphosphine) palladium and dichlorobis (triphenylphosphine) palladium. The usage-amount of the catalyst used is 0.001-0.5 molar equivalent normally with respect to the compound shown by general formula (IV), Preferably it is 0.01-0.2 molar equivalent.
The reaction temperature of the reaction using the compound represented by the general formula (Vc) is usually -80 to 180 ° C, preferably -30 to 150 ° C. The reaction time is usually 30 minutes to 100 hours. Completion of the reaction can be confirmed by sampling a part of the reaction mixture and analyzing means such as thin layer chromatography or high performance liquid chromatography. After completion of the reaction, for example, the reaction mixture and water are mixed, extracted with an organic solvent, and the resulting organic layer is dried, concentrated, and the like, whereby the compound represented by the general formula (II) is obtained. Can be isolated.
The compound represented by the general formula (II) can be produced according to a method according to the method described in, for example, Tetrahedron, Vol. 57, 1323-1330 (2001).
The organometallic reagent represented by the general formula (Va), (Vb) or (Vc) is a known compound, or can be produced from a known compound according to a method according to a known method. .
The compound represented by the general formula (IV) is a known compound or can be produced from a known compound. For example, it can be produced according to a method described in Journal of Heterocyclic Chemistry (J. Heterocycl. Chem.), Vol. 33, pages 1579 to 1582 (1996), or the like.

〔式中、Ｘ³はハロゲン原子（例えば、塩素原子、臭素原子、ヨウ素原子等）を表し、Ｒ¹、Ｒ²、Ｒ⁹、Ｚ¹、Ｚ²及びｎは前記と同じ意味を表す。〕
本反応は通常溶媒中で行なう。使用できる溶媒としては、例えば、アセトニトリル等のニトリル類、アセトン等のケトン類、ベンゼン、トルエン等の芳香族炭化水素類；ジエチルエーテル、ジイソプロピルエーテル、ジオキサン、テトラヒドロフラン、ジメトキシエタン等のエーテル類；ジクロロメタン、クロロホルム、１，２−ジクロロエタン等のハロゲン化炭化水素類；ジメチルホルムアミド、ジメチルアセトアミド等のアミド類；スルホラン等のスルホン類、又はこれらの混合溶媒が挙げられる。
また、本反応は通常、塩基の存在下に一般式（VII）で示される化合物と一般式（VIII）で示される化合物とを反応させるが、本反応において用いられる塩基としては例えば、トリエチルアミン、トリプロピルアミン、ピリジン、ジメチルアミノピリジン、１，８−ジアザビシクロ［５．４．０］−７−ウンデセン、１，４−ジアザビシクロ[２．２．２]オクタン等の有機塩基；水酸化ナトリウム、水酸化カリウム、水酸化カルシウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸カルシウム、水素化ナトリウム等の無機塩基が挙げられる。
本反応において、一般式（VIII）で示される化合物は、一般式（VII）で示される化合物に対して、通常１モル当量以上、好ましくは１〜３モル当量である。塩基は、一般式（VII）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−１０〜５０℃である。本反応の反応時間は通常１０分〜３０時間である。
本反応の終了は、反応混合物の一部をサンプリングして、薄層クロマトグラフィー、高速液体クロマトグラフィー等の分析手段により確認することができる。本反応の終了後、例えば反応混合物と水とを混合し、有機溶媒にて抽出し、得られた有機層を乾燥、濃縮する等の操作を行うことにより、一般式（VI）で示される化合物を単離することができる。
一般式（VII）で示される化合物は、一般式（IX）

〔式中、Ｚ¹、Ｚ²及びｎは前記と同じ意味を表す。〕
で示される化合物をハロゲン化剤（例えば、塩化チオニル、臭化チオニル、オキシ塩化リン、塩化オキサリル等）と反応させることにより製造することができる。
一般式（IX）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、オーガニック・シンセシーズ・コレクティブ・ボリュム（Ｏｒｇａｎｉｃ Ｓｙｎｔｈｅｓｅｓ Ｃｏｌｌｅｃｔｉｖｅ Ｖｏｌｕｍｅ）、３巻、５５７〜５６０頁（１９５５年）、ジャーナル・オブ・アメリカン・ケミカル・ソサエティ（Ｊ．Ａｍ．Ｃｈｅｍ．Ｓｏｃ．）、６３巻、２６４３〜２６４４頁（１９４１年）、国際公開第２００６／０５６２８２号パンフレット（ＷＯ２００６／０５６２８２）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。一般式（IX）で示される化合物としては例えば、２，４，６−トリメチルフェニル酢酸、２，４，６−トリエチルフェニル酢酸、２，６−ジエチル−４−メチルフェニル酢酸、２−エチルフェニル酢酸、２−エチル−４−メチルフェニル酢酸、２−エチル−４，６−ジメチルフェニル酢酸、２，４−ジエチルフェニル酢酸、２，６−ジエチルフェニル酢酸、２，４−ジエチル−６−メチルフェニル酢酸等があげられる。
一般式（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。 Reference production method 2
The compound represented by the general formula (VI) can be produced, for example, by the following production method.

[Wherein X ³ represents a halogen atom (for example, chlorine atom, bromine atom, iodine atom, etc.), and R ¹ , R ² , R ⁹ , Z ¹ , Z ² and n represent the same meaning as described above. ]
This reaction is usually carried out in a solvent. Examples of the solvent that can be used include nitriles such as acetonitrile, ketones such as acetone, aromatic hydrocarbons such as benzene and toluene; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, and dimethoxyethane; dichloromethane, Examples include halogenated hydrocarbons such as chloroform and 1,2-dichloroethane; amides such as dimethylformamide and dimethylacetamide; sulfones such as sulfolane, and mixed solvents thereof.
In this reaction, the compound represented by the general formula (VII) and the compound represented by the general formula (VIII) are usually reacted in the presence of a base. Examples of the base used in this reaction include triethylamine and triethylamine. Organic bases such as propylamine, pyridine, dimethylaminopyridine, 1,8-diazabicyclo [5.4.0] -7-undecene, 1,4-diazabicyclo [2.2.2] octane; sodium hydroxide, hydroxide Examples include inorganic bases such as potassium, calcium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, calcium carbonate, sodium hydride.
In this reaction, the compound represented by the general formula (VIII) is usually 1 molar equivalent or more, preferably 1 to 3 molar equivalents relative to the compound represented by the general formula (VII). A base is 0.5-10 molar equivalent normally with respect to the compound shown by general formula (VII), Preferably it is 1-5 molar equivalent.
The reaction temperature of this reaction is usually −30 to 180 ° C., preferably −10 to 50 ° C. The reaction time for this reaction is usually 10 minutes to 30 hours.
The completion of this reaction can be confirmed by sampling a part of the reaction mixture and analyzing means such as thin layer chromatography or high performance liquid chromatography. After the completion of this reaction, for example, the reaction mixture and water are mixed, extracted with an organic solvent, and the resulting organic layer is dried and concentrated, whereby the compound represented by the general formula (VI) is obtained. Can be isolated.
The compound represented by the general formula (VII) is represented by the general formula (IX)

[Wherein, Z ¹ , Z ² and n represent the same meaning as described above. ]
Can be produced by reacting with a halogenating agent (for example, thionyl chloride, thionyl bromide, phosphorus oxychloride, oxalyl chloride, etc.).
The compound represented by the general formula (IX) is a known compound or can be produced from a known compound. For example, Organic Synthetics Collective Volume, Vol. 3, 557-560 (1955), Journal of American Chemical Society (J. Am. Chem. Soc.), 63. Vol. 2643-2644 (1941), WO 2006/056282 pamphlet (WO 2006/056282) and the like, or a method according to them. Examples of the compound represented by the general formula (IX) include 2,4,6-trimethylphenylacetic acid, 2,4,6-triethylphenylacetic acid, 2,6-diethyl-4-methylphenylacetic acid, 2-ethylphenylacetic acid. 2-ethyl-4-methylphenylacetic acid, 2-ethyl-4,6-dimethylphenylacetic acid, 2,4-diethylphenylacetic acid, 2,6-diethylphenylacetic acid, 2,4-diethyl-6-methylphenylacetic acid Etc.
The compound represented by the general formula (VIII) is a known compound or can be produced from a known compound.

  Each of the compounds produced by the above production methods 1 to 3 or reference production methods 1 to 2 may be other known means such as concentration, concentration under reduced pressure, extraction, phase transfer, crystallization, recrystallization, chromatography, etc. Depending on the method, isolation and purification may be possible.

Next, specific examples of the compound of the present invention are shown below.

1) In the general formulas (I ¹ ) to (I ³⁰ ), Ar is a 2-ethylphenyl group,
G is a hydrogen atom, acetyl group, trifluoroacetyl group, propionyl group, butyryl group, isobutyryl group, isovaleryl group, pivaloyl group, cyclohexylcarbonyl group, benzoyl group, benzylcarbonyl group, methoxycarbonyl group, ethoxycarbonyl group, phenoxycarbonyl group , A pyridazinone compound which is a dimethylaminocarbonyl group, a methanesulfonyl group, a trifluoromethanesulfonyl group, a benzenesulfonyl group or a p-toluenesulfonyl group.

2) In the general formulas (I ¹ ) to (I ³⁰ ), Ar is a 2-propylphenyl group,
G is a hydrogen atom, acetyl group, trifluoroacetyl group, propionyl group, butyryl group, isobutyryl group, isovaleryl group, pivaloyl group, cyclohexylcarbonyl group, benzoyl group, benzylcarbonyl group, methoxycarbonyl group, ethoxycarbonyl group, phenoxycarbonyl group , A pyridazinone compound which is a dimethylaminocarbonyl group, a methanesulfonyl group, a trifluoromethanesulfonyl group, a benzenesulfonyl group or a p-toluenesulfonyl group.

3) In the general formulas (I ¹ ) to (I ³⁰ ), Ar is a 2,4-dimethylphenyl group,
G is a hydrogen atom, acetyl group, trifluoroacetyl group, propionyl group, butyryl group, isobutyryl group, isovaleryl group, pivaloyl group, cyclohexylcarbonyl group, benzoyl group, benzylcarbonyl group, methoxycarbonyl group, ethoxycarbonyl group, phenoxycarbonyl group , A pyridazinone compound which is a dimethylaminocarbonyl group, a methanesulfonyl group, a trifluoromethanesulfonyl group, a benzenesulfonyl group or a p-toluenesulfonyl group.

4) In the general formulas (I ¹ ) to (I ³⁰ ), Ar is a 2,6-dimethylphenyl group,
G is a hydrogen atom, acetyl group, trifluoroacetyl group, propionyl group, butyryl group, isobutyryl group, isovaleryl group, pivaloyl group, cyclohexylcarbonyl group, benzoyl group, benzylcarbonyl group, methoxycarbonyl group, ethoxycarbonyl group, phenoxycarbonyl group , A pyridazinone compound which is a dimethylaminocarbonyl group, a methanesulfonyl group, a trifluoromethanesulfonyl group, a benzenesulfonyl group or a p-toluenesulfonyl group.

5) In the general formulas (I ¹ ) to (I ³⁰ ), Ar is a 2-ethyl-4-methylphenyl group,
G is a hydrogen atom, acetyl group, trifluoroacetyl group, propionyl group, butyryl group, isobutyryl group, isovaleryl group, pivaloyl group, cyclohexylcarbonyl group, benzoyl group, benzylcarbonyl group, methoxycarbonyl group, ethoxycarbonyl group, phenoxycarbonyl group , A pyridazinone compound which is a dimethylaminocarbonyl group, a methanesulfonyl group, a trifluoromethanesulfonyl group, a benzenesulfonyl group or a p-toluenesulfonyl group.

In 6) In formula ^{(I 1) ~ (I 30} ), Ar is a 2-ethyl-6-methylphenyl group,
G is a hydrogen atom, acetyl group, trifluoroacetyl group, propionyl group, butyryl group, isobutyryl group, isovaleryl group, pivaloyl group, cyclohexylcarbonyl group, benzoyl group, benzylcarbonyl group, methoxycarbonyl group, ethoxycarbonyl group, phenoxycarbonyl group , A pyridazinone compound which is a dimethylaminocarbonyl group, a methanesulfonyl group, a trifluoromethanesulfonyl group, a benzenesulfonyl group or a p-toluenesulfonyl group.

7) In the general formulas (I ¹ ) to (I ³⁰ ), Ar is a 2,6-diethylphenyl group,
G is a hydrogen atom, acetyl group, trifluoroacetyl group, propionyl group, butyryl group, isobutyryl group, isovaleryl group, pivaloyl group, cyclohexylcarbonyl group, benzoyl group, benzylcarbonyl group, methoxycarbonyl group, ethoxycarbonyl group, phenoxycarbonyl group , A pyridazinone compound which is a dimethylaminocarbonyl group, a methanesulfonyl group, a trifluoromethanesulfonyl group, a benzenesulfonyl group or a p-toluenesulfonyl group.

8) In the general formulas (I ¹ ) to (I ³⁰ ), Ar is a 2,4,6-trimethylphenyl group,
G is a hydrogen atom, acetyl group, trifluoroacetyl group, propionyl group, butyryl group, isobutyryl group, isovaleryl group, pivaloyl group, cyclohexylcarbonyl group, benzoyl group, benzylcarbonyl group, methoxycarbonyl group, ethoxycarbonyl group, phenoxycarbonyl group , A pyridazinone compound which is a dimethylaminocarbonyl group, a methanesulfonyl group, a trifluoromethanesulfonyl group, a benzenesulfonyl group or a p-toluenesulfonyl group.

9) In the general formulas (I ¹ ) to (I ³⁰ ), Ar is a 2-ethyl-4,6-dimethylphenyl group,
G is a hydrogen atom, acetyl group, trifluoroacetyl group, propionyl group, butyryl group, isobutyryl group, isovaleryl group, pivaloyl group, cyclohexylcarbonyl group, benzoyl group, benzylcarbonyl group, methoxycarbonyl group, ethoxycarbonyl group, phenoxycarbonyl group , A pyridazinone compound which is a dimethylaminocarbonyl group, a methanesulfonyl group, a trifluoromethanesulfonyl group, a benzenesulfonyl group or a p-toluenesulfonyl group.

10) In the general formula ^{(I 1) ~ (I 30} ), wherein Ar is 2,6-diethyl-4-methylphenyl group,
G is a hydrogen atom, acetyl group, trifluoroacetyl group, propionyl group, butyryl group, isobutyryl group, isovaleryl group, pivaloyl group, cyclohexylcarbonyl group, benzoyl group, benzylcarbonyl group, methoxycarbonyl group, ethoxycarbonyl group, phenoxycarbonyl group , A pyridazinone compound which is a dimethylaminocarbonyl group, a methanesulfonyl group, a trifluoromethanesulfonyl group, a benzenesulfonyl group or a p-toluenesulfonyl group.

11) In the general formulas (I ¹ ) to (I ³⁰ ), Ar is a 2,4,6-triethylphenyl group,
G is a hydrogen atom, acetyl group, trifluoroacetyl group, propionyl group, butyryl group, isobutyryl group, isovaleryl group, pivaloyl group, cyclohexylcarbonyl group, benzoyl group, benzylcarbonyl group, methoxycarbonyl group, ethoxycarbonyl group, phenoxycarbonyl group , A pyridazinone compound which is a dimethylaminocarbonyl group, a methanesulfonyl group, a trifluoromethanesulfonyl group, a benzenesulfonyl group or a p-toluenesulfonyl group.
12) In the general formulas (I ¹ ) to (I ³⁰ ), Ar is a 2,4-diethylphenyl group,
G is a hydrogen atom, acetyl group, trifluoroacetyl group, propionyl group, butyryl group, isobutyryl group, isovaleryl group, pivaloyl group, cyclohexylcarbonyl group, benzoyl group, benzylcarbonyl group, methoxycarbonyl group, ethoxycarbonyl group, phenoxycarbonyl group , A pyridazinone compound which is a dimethylaminocarbonyl group, a methanesulfonyl group, a trifluoromethanesulfonyl group, a benzenesulfonyl group or a p-toluenesulfonyl group.
13) In the general formula ^{(I 1) ~ (I 30} ), wherein Ar is a 2,4-diethyl-6-methylphenyl group,
G is a hydrogen atom, acetyl group, trifluoroacetyl group, propionyl group, butyryl group, isobutyryl group, isovaleryl group, pivaloyl group, cyclohexylcarbonyl group, benzoyl group, benzylcarbonyl group, methoxycarbonyl group, ethoxycarbonyl group, phenoxycarbonyl group , A pyridazinone compound which is a dimethylaminocarbonyl group, a methanesulfonyl group, a trifluoromethanesulfonyl group, a benzenesulfonyl group or a p-toluenesulfonyl group.

The present invention also includes a compound represented by general formula (II) and a compound represented by general formula (VI), which are useful production intermediate compounds of the compound represented by general formula (Ia).
As a compound shown by general formula (II), the aspect shown below is mentioned, for example.
In the general formula (II), a compound wherein n is an integer of 1 or more.
In the general formula (II), n is 0 and Z ¹ is a C _2-6 alkyl group.
In the general formula (II), a compound in which n is 1 or 2, and the bonding position of Z ² is the 4-position and / or the 6-position on the benzene ring.
In the general formula (II), a compound wherein R ¹ is a C _1-3 alkyl group or a (C _1-3 alkyloxy) C _1-3 alkyl group.
In the general formula (II), a compound wherein R ² is a hydrogen atom or a C _1-3 alkyl group.
In the general formula (II), compounds wherein R ² is a hydrogen atom or a methyl group.
In the general formula (II), a compound in which Z ¹ is a C _1-3 alkyl group and Z ² is a C _1-3 alkyl group.
In the general formula (II), a compound in which R ¹ is a C _1-3 alkyl group or a (C _1-3 alkyloxy) C _1-3 alkyl group, and R ² is a hydrogen atom or a methyl group.
In the general formula (II), R ¹ is a C _1-3 alkyl group or a (C _1-3 alkyloxy) C _1-3 alkyl group, R ² is a hydrogen atom or a C _1-3 alkyl group,
When n represents an integer of 0, 1 or 2, and n represents 2, two Z ² may be the same or different. When n represents 1 or 2, the bonding position of Z ² is on the benzene ring. 4th and / or 6th
Z ¹ is a C _1-6 alkyl group (more preferably a C _1-3 alkyl group),
A compound in which Z ² is a C _1-6 alkyl group (more preferably a C _1-3 alkyl group).
In the general formula (II), R ¹ is a C _1-3 alkyl group or a (C _1-3 alkyloxy) C _1-3 alkyl group, R ² is a hydrogen atom or a methyl group,
When n represents an integer of 0, 1 or 2, and n represents 2, two Z ² may be the same or different. When n represents 1 or 2, the bonding position of Z ² is on the benzene ring. 4th and / or 6th
Z ¹ is a C _1-6 alkyl group (more preferably a C _1-3 alkyl group),
A compound in which Z ² is a C _1-6 alkyl group (more preferably a C _1-3 alkyl group).

Moreover, as a compound shown by general formula (VI), the aspect shown below is mentioned, for example.
In the general formula (VI), a compound wherein n is an integer of 1 or more.
In the general formula (VI), compounds wherein n is 0 and Z ¹ is a C _2-6 alkyl group.
In the general formula (VI), a compound in which n is 1 or 2, and the bonding position of Z ² is the 4-position and / or the 6-position on the benzene ring.
In the general formula (VI), a compound wherein R ¹ is a C _1-3 alkyl group or a (C _1-3 alkyloxy) C _1-3 alkyl group.
In the general formula (VI), compounds wherein R ² is a C _1-6 alkyl group.
In the general formula (VI), compounds wherein R ² is a hydrogen atom or a C _1-3 alkyl group.
In the general formula (VI), compounds wherein R ² is a C _1-3 alkyl group.
In the general formula (VI), compounds wherein R ² is a hydrogen atom or a methyl group.
In the general formula (VI), compounds wherein R ² is a methyl group.
In the general formula (VI), a compound in which Z ¹ is a C _1-3 alkyl group and Z ² is a C _1-3 alkyl group.
In the general formula (VI), a compound in which R ¹ is a C _1-3 alkyl group or a (C _1-3 alkyloxy) C _1-3 alkyl group, and R ² is a hydrogen atom or a methyl group.
In the general formula (VI), R ¹ is a C _1-3 alkyl group or a (C _1-3 alkyloxy) C _1-3 alkyl group, R ² is a hydrogen atom or a C _1-3 alkyl group,
When n represents an integer of 0, 1 or 2, and n represents 2, two Z ² may be the same or different. When n represents 1 or 2, the bonding position of Z ² is on the benzene ring. 4th and / or 6th
Z ¹ is a C _1-6 alkyl group (more preferably a C _1-3 alkyl group),
A compound in which Z ² is a C _1-6 alkyl group (more preferably a C _1-3 alkyl group).
In the general formula (VI), R ¹ is a C _1-3 alkyl group or a (C _1-3 alkyloxy) C _1-3 alkyl group, R ² is a hydrogen atom or a methyl group,
When n represents an integer of 0, 1 or 2, and n represents 2, two Z ² may be the same or different. When n represents 1 or 2, the bonding position of Z ² is on the benzene ring. 4th and / or 6th
Z ¹ is a C _1-6 alkyl group (more preferably a C _1-3 alkyl group),
A compound in which Z ² is a C _1-6 alkyl group (more preferably a C _1-3 alkyl group).

Examples, Reference Examples, Formulation Examples and Test Examples are shown below to explain the present invention more specifically, but the present invention is not limited to these examples.
In Examples and Reference 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 examples and reference examples have the following meanings.
CDCl ₃ : deuterated chloroform, s: singlet, d: doublet, t: triplet, q: quartet, dt: doublet triplet, dq: doublet quartet, m: multiplet, br. : Broad (wide), J: coupling constant, Me: methyl group, Et: ethyl group, Pr: propyl group, i-Pr: isopropyl group, t-Bu: tertiary butyl group, c-Hex: cyclohexyl group, Ph: phenyl group.

Example 1
4- (2-Ethylphenyl) -5-hydroxy-2-methyl-3 (2H) -pyridazinone [Compound Ia-1]
To 3.193 g of 4- (2-ethylphenyl) -5-methoxy-2-methyl-3 (2H) -pyridazinone [Compound II-1], 50 mL of water, 4.657 g of potassium hydroxide (85% content) and 1 , 4-Dioxane (5 mL) was added, and the mixture was stirred for 36 hours with heating under reflux. After cooling, the reaction mixture was acidified with concentrated hydrochloric acid, and 10 mL of water and 100 mL of ethyl acetate were added. The insoluble material in the mixture was separated by filtration and then separated. The organic layer was washed with water and then with saturated brine. The organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off. The obtained solid was washed with a mixed solvent of ethyl acetate-hexane (1: 2) to obtain 2.050 g of the title compound as colorless crystals.

The compound of the present invention produced according to Example 1 is shown in Table 1 together with Compound Ia-1.
Compound represented by general formula (Ia):

Example 2
4- (2,6-Diethyl-4-methylphenyl) -5-hydroxy-2,6-dimethyl-3 (2H) -pyridazinone [Compound Ia-14]
Under a nitrogen atmosphere, 13 mL of a tetrahydrofuran solution (1 mol / L) of potassium tert-butoxide was stirred at room temperature, and this was added to 2- [2- (2,6-diethyl-4-methylphenylacetyl) -2-methylhydrazono]. A solution of 1.9 g of ethyl propanoate [Compound VI-2] in 55 mL of toluene was added dropwise over about 1 hour, and the mixture was further stirred at room temperature for 30 minutes. The reaction mixture was then concentrated under reduced pressure. To the obtained residue was added 30 mL of ice water, and the mixture was extracted with tert-butyl methyl ether (20 mL × 2). Next, the aqueous layer was acidified by adding 1.6 g of 35% hydrochloric acid, and extracted with ethyl acetate (20 mL × 3). The ethyl acetate extracts were combined, washed with saturated brine (20 mL × 2), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate: hexane = 1: 3) to obtain 0.76 g of a solid. The solid was washed with cold hexane and air dried to give 0.59 g of the title compound as a white powder.

The compound of the present invention produced according to Example 2 is shown in Table 2 together with Compound Ia-14.
Compound represented by general formula (Ia):

Example 3
5-Benzoyloxy-4- (2-ethylphenyl) -2-methyl-3 (2H) -pyridazinone [Compound Ib-1]
To 0.326 g of the compound Ia-1 produced in Example 1, 12 mL of tetrahydrofuran and 0.40 mL of triethylamine were added, ice-cooled, and 0.25 mL of benzoyl chloride was further added. The mixture was stirred for 10 minutes under ice cooling and then for 3 hours at room temperature. 30 mL of water was added to the reaction mixture, and the mixture was extracted twice with 30 mL of ethyl acetate. The extracts were combined, washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was distilled off. The residue was subjected to silica gel column chromatography (ethyl acetate: hexane = 1: 2 → 2: 1) to obtain 0.463 g of the title compound as a colorless oil.

The compound of the present invention produced according to Example 3 is shown in Table 3 together with compound Ib-1.
Compound represented by general formula (Ib):

The ¹ H NMR data of the compounds marked with * in the melting point column in Table 3 are shown below.
Compound Ib-1:
¹ H NMR (CDCl ₃ ) δ ppm: 1.14 (3H, t, J = 7.7 Hz), 2.45-2.62 (2H, m), 3.88 (3H, s), 7.09 -7.12 (1H, m), 7.15-7.20 (1H, m), 7.28-7.30 (2H, m), 7.37-7.42 (2H, m), 7 .55-7.60 (1H, m), 7.81-7.84 (2H, m), 7.95 (1H, s).
Compound Ib-3:
¹ H NMR (CDCl ₃ ) δ ppm: 0.94 (3H, t, J = 7.6 Hz), 1.13 (3H, t, J = 7.7 Hz), 2.27 (2H, dq, J = 1.4, 7.6 Hz), 2.38-2.56 (2H, m), 3.84 (3H, s), 7.00-7.03 (1H, m), 7.18-7. 23 (1H, m), 7.30-7.35 (2H, m), 7.75 (1H, s).
Compound Ib-6:
¹ H NMR (CDCl ₃ ) δ ppm: 1.13 (3H, t, J = 7.7 Hz), 1.10-1.22 (5H, m), 1.5-1.7 (5H, m) , 2.28 (1H, br.), 2.38-2.55 (2H, m), 3.84 (3H, s), 6.99-7.02 (1H, m), 7.17- 7.22 (1H, m), 7.29-7.36 (2H, m), 7.72 (1H, s).
Compound Ib-8:
¹ H NMR (CDCl ₃ ) δ ppm: 1.11 (3H, t, J = 7.7 Hz), 2.40-2.57 (2H, m), 2.64 (3H, s), 2.85 (3H, s), 3.83 (3H, s), 7.05-7.08 (1H, m), 7.19-7.24 (1H, m), 7.30-7.36 (2H M), 7.95 (1H, s).
Compound Ib-9:
¹ H NMR (CDCl ₃ ) δ ppm: 1.18 (3H, t, J = 7.6 Hz), 2.43 to 2.57 (2H, m), 2.58 (3H, s), 3.85 (3H, s), 7.16-7.19 (1H, m), 7.25-7.30 (1H, m), 7.36-7.43 (2H, m), 7.96 (1H , S).

A representative production example of the compound represented by the general formula (II) is shown in Reference Example 1.
Reference example 1
4- (2-Ethylphenyl) -5-methoxy-2-methyl-3 (2H) -pyridazinone [Compound II-1]
To a mixture of 2.516 g of 4-chloro-5-methoxy-2-methyl-3 (2H) -pyridazinone, 2.575 g of 2-ethylphenylboronic acid and 3.333 g of sodium carbonate, 30 mL of 1,4-dioxane and 20 mL of water Further, 2.417 g of tetrabutylammonium bromide and 0.657 g of tetrakis (triphenylphosphine) palladium were added, and the mixture was stirred for 17 hours under a nitrogen atmosphere and heated to reflux. After cooling the reaction mixture, 50 mL of water was added, followed by extraction with 100 mL of ethyl acetate and an additional 30 mL. The extracts were combined, washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was distilled off. The obtained solid was washed with a mixed solvent of ethyl acetate-hexane (1: 2) to obtain 3.238 g of the title compound as yellow crystals.

The compounds represented by the general formula (II) produced according to Reference Example 1 are shown in Table 4 together with the compound II-1.
Compound represented by formula (II):

In Table 4, the ¹ H NMR data of the compounds marked with * in the melting point column are shown below.
Compound II-2:
¹ H NMR (CDCl ₃ ) δ ppm: 1.12 (3H, t, J = 7.7 Hz), 1.39 (3H, t, J = 7.3 Hz), 2.40-2.53 (2H, m), 3.81 (3H, s), 4.19-4.30 (2H, m), 7.10 (1H, d, J = 7.6 Hz), 7.21-7.26 (1H, m), 7.30-7.33 (2H, m), 7.88 (1H, s).
Compound II-4:
¹ H NMR (CDCl ₃ ) δ ppm: 1.12 (3H, t, J = 7.7 Hz), 2.38-2.52 (2H, m), 3.38 (3H, s), 3.82 (3H, s), 3.77-3.84 (2H, m), 4.40 (2H, t, J = 5.6 Hz), 7.11 (1H, d, J = 7.6 Hz), 7.21-7.26 (1H, m), 7.30-7.34 (2H, m), 7.90 (1H, s).
Compound II-7:
¹ H NMR (CDCl ₃ ) δ ppm: 1.08 (3H, t, J = 7.7 Hz), 2.07 (3H, s), 2.30-2.45 (2H, m), 3.81 (3H, s), 3.82 (3H, s), 7.10 (1H, d, J = 7.6 Hz), 7.13 (1H, d, J = 7.6 Hz), 7.24 (1H , T, J = 7.6 Hz), 7.85 (1H, s).

A typical production example of the compound represented by the general formula (Va) is shown in Reference Example 2.
Reference example 2
15.5 mL of 2-propylphenylboronic acid butyllithium (1.6 mol / L hexane solution) was put in a reaction vessel, cooled in a dry ice-acetone bath, and 4.412 g of 2-propylbromobenzene dissolved in 45 mL of tetrahydrofuran. Was added dropwise at −70 ° C. over 85 minutes in a nitrogen atmosphere. The mixture was stirred at −70 ° C. for 30 minutes, and 3.75 mL of trimethyl borate was added dropwise at −70 ° C. over 15 minutes. The mixture was stirred at -70 ° C for 1 hour, and then cooling with a dry ice-acetone bath was stopped, followed by stirring at room temperature for 18 hours. To the reaction mixture, 2N hydrochloric acid (33 mL) was added dropwise over 10 minutes, followed by stirring at room temperature for 4 hours. 20 mL of water was added to the mixture, and the mixture was extracted with 70 mL of ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was subjected to silica gel column chromatography (ethyl acetate: hexane = 1: 2 → 2: 1) to obtain 1.641 g of the title compound as colorless crystals.
¹ H NMR (CDCl ₃ ) δ ppm: 1.01 (3H, t, J = 7.4 Hz), 1.69-1.79 (2H, m), 3.15-3.20 (2H, m) 4.0-6.0 (2H, br.), 7.28-7.33 (2H, m), 7.47 (1H, dt, J = 1.5, 7.6 Hz), 8.20. -8.23 (1H, m).

According to Reference Example 2, a compound represented by the following general formula (Va) was produced.
2-Ethyl-6-methylphenylboronic acid:
mp 90-91 ° C.
¹ H NMR (CDCl ₃ ) δ ppm: 1.22 (3H, t, J = 7.6 Hz), 2.35 (3H, s), 2.64 (2H, q, J = 7.6 Hz), 4 0.0-5.5 (2H, br.), 6.98 (1H, d, J = 7.7 Hz), 7.01 (1H, d, J = 7.7 Hz), 7.18 (1H, t , J = 7.7 Hz).
2,6-Diethyl-4-methylphenylboronic acid:
mp 111-113 ° C.
¹ H NMR (CDCl ₃ ) δ ppm: 1.23 (6H, t, J = 7.7 Hz), 2.31 (3H, s), 2.63 (4H, q, J = 7.7 Hz), 4 0.0-5.0 (2H, br.), 6.88 (2H, s).

A representative production example of the compound represented by the general formula (VI) is shown in Reference Example 3.
Reference example 3
2- [2- (2,6-Diethyl-4-methylphenylacetyl) -2-methylhydrazono] ethyl propanoate [Compound VI-2]
To a solution of 2.0 g of ethyl 2- (methylhydrazono) propanoate in 35 mL of acetonitrile was added 1.5 g of potassium carbonate. The mixture was stirred under ice-cooling, and a solution of 2.6 g of 2,6-diethyl-4-methylphenylacetyl chloride in 10 mL of acetonitrile was added dropwise over about 20 minutes, and the mixture was further stirred at room temperature for 3.5 hours. . The reaction mixture was then concentrated under reduced pressure. 20 mL of ice water was added to the obtained residue, and the mixture was extracted with ethyl acetate (20 mL × 3). The extracts were combined, washed with saturated brine (20 mL × 2), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to basic alumina column chromatography (ethyl acetate: hexane = 1: 3) to obtain 1.9 g of the title compound as white crystals.

The compounds represented by the general formula (VI) produced according to Reference Example 3 are shown in Table 5 together with the compound VI-2.
Compound represented by formula (VI):

In Table 5, ¹ H NMR data of the compounds marked with * in the melting point column are shown below.
Compound VI-3:
¹ H NMR (CDCl ₃ ) δ ppm: 1.19 (3H, t, J = 7.6 Hz), 1.37 (3H, t, J = 7.2 Hz), 2.20 (3H, br.s) , 2.67 (2H, q, J = 7.7 Hz), 3.37 (3H, br. S), 4.03 (2H, br. S), 4.33 (2H, q, J = 7. 0 Hz), 7.06-7.30 (4H, m).
Compound VI-4:
¹ H NMR (CDCl ₃ ) δ ppm: 1.18 (3H, t, J = 7.6 Hz), 1.37 (3H, t, J = 7.2 Hz), 2.20 (3H, br.s) , 2.30 (3H, s), 2.63 (2H, q, J = 7.7 Hz), 3.36 (3H, br. S), 3.99 (2H, br. S), 4.33 (2H, q, J = 7.1 Hz), 6.93 (1H, br.d, J = 7.1 Hz), 7.00 (1H, br.s), 7.12 (1H, br.d, J = 7.8 Hz).
Compound VI-6:
¹ H NMR (CDCl ₃ ) δ ppm: 1.16 (3H, t, J = 7.7 Hz), 1.36 (3H, t, J = 7.2 Hz), 2.22 (3H, s), 2 .27 (3H, s), 2.30 (3H, br. S), 2.56 (2H, q, J = 7.7 Hz), 3.39 (3H, br. S), 4.02 (2H) , Br.s), 4.32 (2H, q, J = 7.1 Hz), 6.86 (2H, br.s).
Compound VI-7 (E / Z isomer mixture):
¹ H NMR (CDCl ₃ ) δ ppm: 1.13 to 1.25 (9H, m), 1.31 to 1.41 (3H, m), 2.29 (3H, s), 2.50 to 2 .81 (6H, m), 3.23, 3.43 (3H, ech br.s), 4.05 (2H, br. S), 4.27 to 4.39 (2H, m), 6. 89 (2H, s).
Compound VI-8 (E / Z isomer mixture):
¹ H NMR (CDCl ₃ ) δ ppm: 1.06-1.22 (6H, m), 1.31-1.40 (3H, m), 2.30, 2.31 (3H, each), 2.50-2.70 (4H, m), 3.22, 3.38 (3H, each), 4.00 (2H, br.s), 4.27-4.37 (2H, m) 6.90-6.98 (1H, m), 6.98-7.02 (1H, m), 7.02-7.14 (1H, m).
Compound VI-9 (E / Z isomer mixture):
¹ H NMR (CDCl ₃ ) δ ppm: 1.12 to 1.25 (6H, m), 1.31 to 1.41 (3H, m), 2.22 (3H, s), 2.27 (3H , S), 2.50 to 2.81 (4H, m), 3.23, 3.43 (3H, ech br. S), 4.02 (2H, br. S), 4.26 to 4. 37 (2H, m), 6.87 (2H, br. S).
Compound VI-10 (E / Z isomer mixture):
¹ H NMR (CDCl ₃ ) δ ppm: 1.16 to 1.24 (3H, m), 1.32 to 1.40 (3H, m), 2.22 (6H, s), 2.25 (3H , S), 2.55 to 2.80 (2H, m), 3.23, 3.43 (3H, each br.s), 4.00 (2H, br.s), 4.27-4. 38 (2H, m), 6.85 (2H, s).
Compound VI-11
¹ H NMR (CDCl ₃ ) δ ppm: 1.18 (6H, t, J = 7.6 Hz), 1.24 (6H, d, J = 6.8 Hz), 1.37 (3H, t, J = 7.1 Hz), 2.29 (3H, s), 2.55 (4H, q, J = 7.6 Hz), 2.85 (1H, septet, J = 6.8 Hz), 3.22 (3H, s), 4.04 (2H, s), 4.34 (2H, q, J = 7.2 Hz), 6.88 (2H, s).
Compound VI-12 (E / Z isomer mixture):
¹ H NMR (CDCl ₃ ) δ ppm: 1.01 (3H, t, J = 7.4 Hz), 1.17 (6H, t, J = 7.6 Hz), 1.31-1.40 (3H, m), 1.57 to 1.74 (2H, m), 2.30 (3H, s), 2.50 to 2.76 (6H, m), 3.22, 3.42 (3H, each s ), 4.03, 4.05 (2H, ech br.s), 4.26 to 4.36 (2H, m), 6.89 (2H, s).
Compound VI-13 (E / Z isomer mixture):
¹ H NMR (CDCl ₃ ) δ ppm: 1.13 to 1.28 (12H, m), 1.30 to 1.40 (3H, m), 2.50 to 2.80 (8H, m), 3 .23, 3.44 (3H, each), 4.06 (2H, br.s), 4.28 to 4.39 (2H, m), 6.91 (2H, s).
Compound VI-14 (E / Z isomer mixture):
¹ H NMR (CDCl ₃ ) δ ppm: 1.01 (3H, br.t, J = 7.2 Hz), 1.13 to 1.26 (9H, m), 1.30 to 1.40 (3H, m), 1.56-1.73 (2H, m), 2.50-2.76 (8H, m), 3.22, 3.42 (3H, each), 4.03, 4.06 (2H, ech br.s), 4.26-4.37 (2H, m), 6.91 (2H, s).
Compound VI-15:
¹ H NMR (CDCl ₃ ) δ ppm: 1.15 to 1.25 (6H, m), 1.37 (3H, t, J = 7.2 Hz), 2.20 (3H, br.s), 2 .55 to 2.70 (4H, m), 3.36 (3H, br. S), 3.99 (2H, br. S), 4.33 (2H, q, J = 7.1 Hz), 6 .96 (1H, br.d, J = 7.3 Hz), 7.02 (1H, br.s), 7.15 (1H, br.d, J = 7.8 Hz).
Compound VI-16 (E / Z isomer mixture):
¹ H NMR (CDCl ₃ ) δ ppm: 1.05 to 1.25 (9H, m), 1.32 to 1.40 (3H, m), 2.50 to 2.69 (6H, m), 3 .22, 3.38 (3H, each), 4.00 (2H, br.s), 4.26 to 4.36 (2H, m), 6.93 to 7.00 (1H, m), 7.00 to 7.04 (1H, m), 7.06 to 7.18 (1H, m).
Compound VI-17:
¹ H NMR (CDCl ₃ ) δ ppm: 1.17 (3H, t, J = 7.6 Hz), 1.22 (3H, t, J = 7.6 Hz), 1.36 (3H, t, J = 7.1 Hz), 2.24 (3 H, s), 2.30 (3 H, br. S), 2.58 (4 H, q, J = 7.6 Hz), 3.40 (3 H, br. S) 4.03 (2H, br.s), 4.32 (2H, q, J = 7.2 Hz), 6.89 (2H, s).
Compound VI-18:
¹ H NMR (CDCl ₃ ) δ ppm: 1.19 (6H, t, J = 7.6 Hz), 1.36 (3H, t, J = 7.2 Hz), 2.32 (3H, br.s) , 2.60 (4H, q, J = 7.7 Hz), 3.40 (3H, br. S), 4.09 (2H, br. S), 4.33 (2H, q, J = 7. 2 Hz), 7.07 (2H, d, J = 7.6 Hz), 7.18 (1 H, t, J = 7.6 Hz).

Formulation Example 1
Emulsion Compound Ia-1 20% by weight
Polyoxyethylene alkyl ether 5% by weight
Dimethylformamide 18% by weight
Xylene 57% by weight
Are mixed to obtain an emulsion. The prepared emulsion is used after appropriately diluted with water.
Instead of Compound Ia-1, emulsions of Compounds Ia-2 to Ia-30 and Ib-1 to Ib-35 are obtained in the same manner.

Formulation Example 2
Wetting Agent Compound Ib-2 50% by weight
Sodium lignin sulfonate 5% by weight
Polyoxyethylene alkyl ether 5% by weight
5% white carbon
Clay 35% by weight
To obtain a wettable powder. The prepared wettable powder is used after appropriately diluted with water.

Formulation Example 3
Granule Compound Ia-12 1.5% by weight
2% by weight sodium lignin sulfonate
Talc 40% by weight
Bentonite 56.5% by weight
Are mixed and kneaded and granulated to obtain granules.

Formulation Example 4
10 parts of the compound (Ia-12) of the present invention and 10 parts of any one compound selected from the following group A, 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, and synthetic silicon hydroxide-containing fine powder Add 20 parts and 54 parts of diatomaceous earth, mix well, and mix to obtain wettable powder.

Group A:
Phenoxy fatty acid herbicidal compounds [2,4-PA, MCP, MCPB, phenothiol, mecoprop, fluroxypyr, triclopyr, clomeprop, naproanilide, nap
Benzoic acid herbicidal compounds [2,3,6-TBA, dicamba, clopyralid, picloram, aminopyralid, quinclorac, quinmerac],
Urea-based herbicidal compounds [diuron, linuron, chlortoluron, isoproturon, fluometuron, isouron, tebuthiuron, tebuthiuron, tebuthiuron, Cumyluron (cumyluron), daimron (daimuron), methyl-daimlon (methyl-daimuron)
Triazine herbicidal compounds [atrazine, ametrine, cyanazine, simazine, propazine, simetrin, dimethamethrin] , Triaziflam],
Bipyridinium herbicidal compounds [paraquat, diquat],
Hydroxybenzonitrile-based herbicidal compounds [bromoxynil, ioxynil],
Dinitroaniline herbicidal compound [pendimethalin, prodiamine, trifluralin],
Organophosphorus herbicidal compounds [amiprofos-methyl, butamifos, bensulide, piperophos, anilophos, glyphosate, glufosinate, glufosinate )],
Carbamate-based herbicidal compounds [di-allate, tri-allate, EPTC, butyrate, benthocarb, esprocarb, molinate, dipipeperate swep, chlorpropham, phenmedifam, phenisopham, piributicalb, ashram],
Acid amide-based herbicidal compounds [propanil, propyzamide, bromobutide, etobenzanide],
Chloroacetanilide herbicidal compounds [acetochlor, alachlor, butachlor, dimethenamide, propachlor, metazachlor or retrachlor, pretrachlor ), Tenylchlor (theny1ch1or), petoxamide (petoxamide)],
Diphenyl ether-based herbicidal compounds [acifluorfen-sodium, bifenox, oxyfluorfen, lactofen, fomesafen, clomethoxythoniphen, clomethoxythoniphen,
Cyclic imide-based herbicidal compounds [oxadiazon, cinidon-ethyl, carfentrazone-ethyl, sulfentrazone, flumicrolac-pentyl, flumioxazin (Flumioxazin), pyraflufen-ethyl, oxadiargyl (oxadiargyl), pentoxazone, fluthiacet-methyl, butafenacil, benzdifen.
Pyrazole herbicidal compounds [benzofenap, pyrazolate, pyrazoxifene, topramzone, pyrasulfotole],
Triketone herbicidal compounds [isoxaflutole, benzobicyclon, sulcotrione, mesotrione, tembotrione, tefuryltrione, tefuryltrione
Aryloxyphenoxypropionic acid-based herbicidal compounds [clodinahop-propargyl, cyhalofop-butyl, diclohop-methyl, phenoxaprop-ethyl Adihopbutyl (halozyfop-butyl), haloxyhop-methyl, quizalofop-ethyl, metamihop (metamihop)],
Trione oxime herbicidal compounds [aloxydim-sodium, cetoxydim, butroxydim, clesodim, cloproxidim, texixydim, texydimoxime] traxoxydim), profoxydim],
Sulfonylurea herbicidal compounds [chlorsulfuron, sulfomethuron-methyl, metsulfuron-methyl, chlorimuron-ethyl, tribenuron-methyl -Methyl), triasulfuron, trisulfuron-methyl, benzosulfuron-methyl, pyrazosulfuron-ethyl, primisulfuron methyl, Leflon furon), amidosulfuron, minosulfuron, imazosulfuron, rimsulfuron, halosulfuron methyl, sulfuluron-thulfuron , Triflusulfuron-methyl, flazasulfuron, cyclosulfamuron, flupirsulfuron, sulfosulfurfurone, sulfosulfurimuron Azisulfulon, ethoxysulfuron, oxasulfuron, iodosulfuron-methyl-sodium, foramsulfuron, mesosulfuron methyl, messulfuron methyl Cisulfuron, tritosulfuron, orthosulfamuron, flucetosulfuron],
Imidazolinone-type herbicidal compounds [imazametabenz-methyl, imazamethapyr, imazamox, imazapyr, imazaquin (imazaqir), imazaquin (imazaqir)]
Sulfonamide herbicidal compounds [flumetslam, metosulam, dicloslam, floraslam, chloranthramx, penoxsulx, penoxsulx, penoxsulx
Pyrimidinyloxybenzoic acid herbicidal compounds [pyrithiobac-sodium, bispyribac-sodium, pyriminobac-methy1, pyribenzoxim, pyrifolidomid p Pyrimisulfan],
Other strains of herbicidal compounds [bentazone, bromacil, terbacil, chlorthiamid, isoxaben, dinoseb, amitrole, cinmethyline, cinmethyline] tripiphane, dalapon (da1apon), diflufenzopyr sodium (diflufenzopyr-sodium), dithiopyr (dithiopyr), thiazopyr (thiazopyr), sodium flucarbazone (profluzazone) Nasset (mefenacet), flufenacet (flufenacet), fentrazamide (fentrazamide), caffenstrole (cafenstrom), indanophan (indanofan), oxadichromemephone (oxaneclomefone), fidarate (benduresate) (Norflurazon), flurtamon, diflufenican, picolinafene, beflubutamid, clomazone, amicarbazone , Pinoxaden (pinoxaden), pyraclonil (pyraclonil), pyroxasulfone (pyroxasulfone), thien-carbazone methyl (thiencarbazone-methyl)],
Safener compounds [furilazole, dichlormid, benoxacor, alidochlor, isoxadifen-ethyl, fenchlorazole diethyl-ethyl, (Mefenpyr-diethyl), croquintocet-mexyl, fencrolim, cyprosulfamide, ciomethrinil, oxabetrinxyl azole), 1,8-naphthalic anhydride (1,8-Naphthalic Anhydride)].

Formulation Example 5
10 parts of the compound of the present invention (Ia-13) and 10 parts of any one of the compounds selected from Group A, 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, and synthetic silicon hydroxide-containing fine powder Add 20 parts and 54 parts of diatomaceous earth, mix well, and mix to obtain wettable powder.

Formulation Example 6
10 parts of the compound of the present invention (Ia-14) and 10 parts of any one of the compounds selected from Group A, 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, and synthetic silicon hydroxide-containing fine powder Add 20 parts and 54 parts of diatomaceous earth, mix well, and mix to obtain wettable powder.

Formulation Example 7
10 parts of the compound of the present invention (Ia-15) and 10 parts of any one of the compounds selected from Group A, 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, and synthetic silicon hydroxide-containing fine powder Add 20 parts and 54 parts of diatomaceous earth, mix well, and mix to obtain wettable powder.

Formulation Example 8
10 parts of the compound of the present invention (Ia-16) and 10 parts of any one of the compounds selected from Group A, 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, and synthetic silicon hydroxide-containing fine powder Add 20 parts and 54 parts of diatomaceous earth, mix well, and mix to obtain wettable powder.

Formulation Example 9
10 parts of the compound (Ia-17) of the present invention and 10 parts of any one of the compounds selected from the above group A, 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, and synthetic silicon hydroxide-containing fine powder Add 20 parts and 54 parts of diatomaceous earth, mix well, and mix to obtain wettable powder.

Formulation Example 10
10 parts of the compound of the present invention (Ia-18) and 10 parts of any one of the compounds selected from Group A, 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, and synthetic silicon hydroxide-containing fine powder Add 20 parts and 54 parts of diatomaceous earth, mix well, and mix to obtain wettable powder.

Formulation Example 11
10 parts of the compound of the present invention (Ia-19) and 10 parts of any one of the compounds selected from the group A, 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, and fine powder of synthetic silicon hydroxide Add 20 parts and 54 parts of diatomaceous earth, mix well, and mix to obtain wettable powder.

Formulation Example 12
10 parts of the compound (Ib-12) of the present invention and 10 parts of any one of the compounds selected from Group A, 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, and synthetic silicon hydroxide-containing fine powder Add 20 parts and 54 parts of diatomaceous earth, mix well, and mix to obtain wettable powder.

Formulation Example 13
10 parts of the compound (Ib-14) of the present invention and 10 parts of any one of the compounds selected from the above group A, 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, and synthetic silicon hydroxide-containing fine powder Add 20 parts and 54 parts of diatomaceous earth, mix well, and mix to obtain wettable powder.

Formulation Example 14
10 parts of the compound (Ib-16) of the present invention and 10 parts of any one of the compounds selected from the above group A, 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, and synthetic silicon hydroxide-containing fine powder Add 20 parts and 54 parts of diatomaceous earth, mix well, and mix to obtain wettable powder.

Formulation Example 15
10 parts of the compound of the present invention (Ib-18) and 10 parts of any one of the compounds selected from the above group A, 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, and synthetic silicon hydroxide fine powder Add 20 parts and 54 parts of diatomaceous earth, mix well, and mix to obtain wettable powder.

Formulation Example 16
10 parts of the compound of the present invention (Ib-19) and 10 parts of any one of the compounds selected from Group A, 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, and synthetic silicon hydroxide-containing fine powder Add 20 parts and 54 parts of diatomaceous earth, mix well, and mix to obtain wettable powder.

Formulation Example 17
10 parts of the compound of the present invention (Ib-20) and 10 parts of any one of the compounds selected from Group A, 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, and synthetic silicon hydroxide-containing fine powder Add 20 parts and 54 parts of diatomaceous earth, mix well, and mix to obtain wettable powder.

Formulation Example 18
10 parts of the compound (Ib-21) of the present invention and 10 parts of any one of the compounds selected from the group A, 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, and synthetic silicon hydroxide-containing fine powder Add 20 parts and 54 parts of diatomaceous earth, mix well, and mix to obtain wettable powder.

Formulation Example 19
Compound (Ia-12), (Ia-13), (Ia-14), (Ia-15), (Ia-16), (Ia-17) of the present invention , (Ia-18), (Ia-19), (Ib-12), (Ib-14), (Ib-16), (Ib-18), ( 10 parts of (Ib-19), (Ib-20) or (Ib-21) and 10 parts of flumioxazin, 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, synthetic silicon hydroxide Add 20 parts of fine powder and 54 parts of diatomaceous earth and mix well to obtain a wettable powder.

Formulation Example 20
Compound (Ia-12), (Ia-13), (Ia-14), (Ia-15), (Ia-16), (Ia-17) of the present invention , (Ia-18), (Ia-19), (Ib-12), (Ib-14), (Ib-16), (Ib-18), ( Ib-19), (Ib-20) or (Ib-21) 5 parts and glyphosate 25 parts, sodium lauryl sulfate 4 parts, calcium lignin sulfonate 2 parts, Add 20 parts of powder and 44 parts of diatomaceous earth and mix well to obtain a wettable powder.

も供試した。
その結果、化合物Ｉ−ａ−１、Ｉ−ａ−５、Ｉ−ａ−６、Ｉ−ａ−７、Ｉ−ａ−８、Ｉ−ａ−９、Ｉ−ａ−１２、Ｉ−ｂ−１、Ｉ−ｂ−２、Ｉ−ｂ−４、Ｉ−ｂ−５、Ｉ−ｂ−７、Ｉ−ｂ−１０及びＩ−ｂ−１１は５００ｇ／ｈａの処理薬量で効力７以上を示し、化合物Ｉ−ａ−１３、Ｉ−ａ−１４、Ｉ−ａ−１５、Ｉ−ａ−１６、Ｉ−ａ−１７、Ｉ−ａ−１８、Ｉ−ａ−１９、Ｉ−ａ−２０、Ｉ−ａ−２１、Ｉ−ａ−２２、Ｉ−ａ−２７、Ｉ−ｂ−１２、Ｉ−ｂ−１３、Ｉ−ｂ−１４、Ｉ−ｂ−１６、Ｉ−ｂ−１７、Ｉ−ｂ−１８、Ｉ−ｂ−２０、Ｉ−ｂ−２１、Ｉ−ｂ−２２、Ｉ−ｂ−２３及びＩ−ｂ−２５は２５０ｇ／ｈａの処理薬量で効力７以上を示した。対して、化合物Ａは５００ｇ／ｈａの処理薬量で効力１であった。 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 is filled with a commercially grown seedling culture soil, seeded with wheat and covered with about 0.5 cm of soil, and then in a greenhouse Cultivated for a predetermined period. When the plant grew to the 1st to 2nd leaf stage, a drug dilution solution containing Compound Ia-1 was uniformly sprayed over the entire plant at a predetermined treatment dose. The drug diluent is prepared by dissolving a predetermined amount of Compound Ia-1 in a dimethylformamide solution (2%) of Tween 20 (polyoxyethylene sorbitan fatty acid ester, manufactured by MP Biomedicals, Inc.) and diluting with deionized water. Was prepared. Plants after chemical treatment were cultivated in a greenhouse, and after 20 days of treatment, the effect of controlling wheat was observed and evaluated, and was shown in 11 stages of 0 to 10 (0 was no action, 10 was completely dead, 9).
Similarly, other compounds of the present invention and compound A described in Journal of Heterocyclic Chemistry (Vol. 42), pages 427-435 (2005) as a comparative example.

Also tried.
As a result, compounds Ia-1, Ia-5, Ia-6, Ia-7, Ia-8, Ia-9, Ia-12, Ib- 1, Ib-2, Ib-4, Ib-5, Ib-7, Ib-10 and Ib-11 have a potency of 7 or more at a treatment dose of 500 g / ha. Compounds Ia-13, Ia-14, Ia-15, Ia-16, Ia-17, Ia-18, Ia-19, Ia-20 Ia-21, Ia-22, Ia-27, Ib-12, Ib-13, Ib-14, Ib-16, Ib-17, I -B-18, Ib-20, Ib-21, Ib-22, Ib-23 and Ib-25 showed a potency of 7 or more at a treatment dose of 250 g / ha. In contrast, Compound A was potency 1 at a treatment dose of 500 g / ha.

Test Example 2 Field Sprouting Pretreatment Test A plastic case (32 cm × 22 cm × 8 cm in height) was filled with steam-sterilized soil, and seeds of walnuts were planted thereon to cover about 0.5 cm of soil. Subsequently, the chemical | medical agent dilution liquid containing compound I-a-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. Plants after chemical treatment were cultivated in a greenhouse, and after 3 weeks of treatment, the efficacy of controlling pestas was observed and evaluated, and the results were shown in 11 stages from 0 to 10 as in Test Example 1.
Similarly, other compounds of the present invention and compound A as a comparative example were also tested.
As a result, compounds Ia-1, Ia-2, Ia-4, Ia-5, Ia-6, Ia-8, Ia-9, Ia- 10, Ib-1, Ib-5, Ib-6, Ib-7, and Ib-11 show potency 8 or more at a treatment dose of 500 g / ha, and compound Ia -12, Ia-13, Ia-14, Ia-15, Ia-16, Ia-17, Ia-18, Ia-19, Ia-20 Ia-21, Ia-22, Ia-23, Ib-13, Ib-14, Ib-16, Ib-18, Ib-19, I -B-20, Ib-21, Ib-22 and Ib-23 showed potency 8 or higher at a treatment dose of 250 g / ha. In contrast, Compound A was potency 1 at a treatment dose of 500 g / ha.

  Weeds can be controlled by applying an effective amount of the compound of the present invention to weeds or soil where weeds grow.

Claims (15)

Formula (I)

[Wherein R ¹ represents a C _1-6 alkyl group or a (C _1-6 alkyloxy) C _1-6 alkyl group,
R ² represents a hydrogen atom or a C _1-6 alkyl group,
G is a hydrogen atom or the following formula

{Wherein L represents an oxygen atom or a sulfur atom,
R ³ is a C _1-6 alkyl group, C _3-8 cycloalkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _6-10 aryl group, (C _6-10 aryl) C _1-6 Alkyl group, C _1-6 alkyloxy group, C _3-8 cycloalkyloxy group, C _2-6 alkenyloxy group, C _2-6 alkynyloxy group, C _6-10 aryloxy group, (C _6-10 aryl) ) C _1-6 alkyloxy group, amino group, C _1-6 alkylamino group, C _2-6 alkenylamino group, C _6-10 arylamino group, di (C _1-6 alkyl) amino group, di (C _2-6 alkenyl) amino group, (C _1-6 alkyl) (C _6-10 aryl) amino group or 3-8 membered nitrogen-containing heterocyclic group,
R ⁴ represents a C _1-6 alkyl group, a C _6-10 aryl group, a C _1-6 alkylamino group or a di (C _1-6 alkyl) amino group,
R ⁵ and R ⁶ may be the same or different and are a C _1-6 alkyl group, a C _3-8 cycloalkyl group, a C _2-6 alkenyl group, a C _6-10 aryl group, a C _1-6 alkyloxy group. C _3-8 cycloalkyloxy group, C _6-10 aryloxy group, (C _6-10 aryl) C _1-6 alkyloxy group, C _1-6 alkylthio group, C _1-6 alkylamino group or di ( C _1-6 alkyl) represents an amino group.
However, any group represented by R ³ , R ⁴ , R ⁵ and R ⁶ may be substituted with a halogen atom, and may be a C _3-8 cycloalkyl group, a C _6-10 aryl group, (C _{6- 10} aryl) C _1-6 alkyl group aryl moiety, C _3-8 cycloalkyloxy group, C _6-10 aryloxy group, (C _6-10 aryl) C _1-6 alkyloxy group aryl moiety, C _{6 The} aryl moiety of the _-10 arylamino group, the aryl moiety of the (C _1-6 alkyl) (C _6-10 aryl) amino group, and the 3- to 8-membered nitrogen-containing heterocyclic group are substituted with a C _1-6 alkyl group. May be. }
Any one of the groups represented by
Z ¹ represents a C _1-6 alkyl group, Z ² represents a C _1-6 alkyl group, n represents 0, 1, 2, 3 or 4, and when n represents an integer of 2 or more, Z ² may be the same or different.
However, the total number of carbon atoms in the group represented by Z ¹ and n Z ² is 2 or more. ]
A pyridazinone compound represented by: The pyridazinone compound according to claim 1, wherein n is an integer of 1 or more. The pyridazinone compound according to claim ¹ , wherein n is 0 and Z ¹ is a C _2-6 alkyl group. The pyridazinone compound according to claim 1, wherein n is 1 or 2, and the bonding position of Z ² is the 4-position and / or the 6-position on the benzene ring. The pyridazinone compound according to claim 1, 2 or 4, wherein Z ¹ is a C _1-3 alkyl group and Z ² is a C _1-3 alkyl group. G is a hydrogen atom or the following formula

[Wherein R ^3b represents a C _1-6 alkyl group, a C _3-8 cycloalkyl group, a C _2-6 alkenyl group, a C _2-6 alkynyl group, a C _6-10 aryl group, (C _6-10 aryl) C _1-6 alkyl group, C _1-6 alkyloxy group, C _3-8 cycloalkyloxy group, C _6-10 aryloxy group, (C _6-10 aryl) C _1-6 alkyloxy group, C _{1- Represents a 6} alkylamino group, a C _6-10 arylamino group or a di (C _1-6 alkyl) amino group,
R ^4b represents a C _1-6 alkyl group or a C _6-10 aryl group,
R ^5b and R ^6b may be the same or different and each represents a C _1-6 alkyl group, a C _1-6 alkyloxy group, a C _6-10 aryloxy group, or a C _1-6 alkylthio group.
However, any group represented by R ^3b , R ^4b , R ^5b and R ^6b may be substituted with a halogen atom, and may be a C _3-8 cycloalkyl group, a C _6-10 aryl group, (C _{6- 10} aryl) C _1-6 alkyl group aryl moiety, C _3-8 cycloalkyloxy group, C _6-10 aryloxy group, (C _6-10 aryl) C _1-6 alkyloxy group aryl moiety, C ₆ The aryl moiety of the _-10 arylamino group may be substituted with a C _1-6 alkyl group. ]
The pyridazinone compound according to any one of claims 1 to 5, which is any group represented by the formula: G is a hydrogen atom or the following formula

[Wherein R ^3a represents a C _1-6 alkyl group, a C _3-8 cycloalkyl group, a C _6-10 aryl group, a C _1-6 alkyloxy group or a di (C _1-6 alkyl) amino group,
R ^4a represents a C _1-6 alkyl group.
However, any group represented by R ^3a and R ^4a may be substituted with a halogen atom, and the C _3-8 cycloalkyl group and the C _6-10 aryl group are substituted with a C _1-6 alkyl group. May be. ]
The pyridazinone compound according to any one of claims 1 to 5, which is any group represented by the formula: The pyridazinone compound according to any one of claims 1 to 7, wherein R ² is a hydrogen atom or a C _1-3 alkyl group. Pyridazinone compound according to any of claims 1 to 7 R ² is a hydrogen atom or a methyl group. The pyridazinone compound according to any one of claims 1 to 9, wherein R ¹ is a C _1-3 alkyl group or a (C _1-3 alkyloxy) C _1-3 alkyl group. A herbicide containing the pyridazinone compound according to any one of claims 1 to 10 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 10 is applied to weeds or soil where weeds grow. Use of the pyridazinone compound according to any one of claims 1 to 10 for controlling weeds. Formula (II)

[Wherein R ⁷ represents a C _1-6 alkyl group,
R ¹ represents a C _1-6 alkyl group or a (C _1-6 alkyloxy) C _1-6 alkyl group,
R ² represents a hydrogen atom or a C _1-6 alkyl group,
Z ¹ represents a C _1-6 alkyl group, Z ² represents a C _1-6 alkyl group, n represents 0, 1, 2, 3 or 4, and when n represents an integer of 2 or more, Z ² may be the same or different.
However, the total number of carbon atoms in the group represented by Z ¹ and n Z ² is 2 or more. ]
A compound represented by General formula (VI)

[Wherein R ⁹ represents a C _1-6 alkyl group,
R ¹ represents a C _1-6 alkyl group or a (C _1-6 alkyloxy) C _1-6 alkyl group,
R ² represents a hydrogen atom or a C _1-6 alkyl group,
Z ¹ represents a C _1-6 alkyl group, Z ² represents a C _1-6 alkyl group, n represents 0, 1, 2, 3 or 4, and when n represents an integer of 2 or more, Z ² may be the same or different.
However, the total number of carbon atoms in the group represented by Z ¹ and n Z ² is 2 or more. ]
A compound represented by