JP2008169121A - Jasmonic acid derivative, herbicide and herbicidal effect-reinforcing agent - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a jasmonic acid derivative showing an herbicidal effect and/or herbicidal effect-reinforcing effect. <P>SOLUTION: This new jasmonic acid derivatives expressed by formula (I) [wherein, R<SP>1</SP>is an alkyl or an alkenyl; Q is any of the above (Q-1) to (Q-3); R<SP>2</SP>, R<SP>3</SP>, R<SP>6</SP>and R<SP>7</SP>are each H, an alkyl or the like; R<SP>4</SP>, R<SP>5</SP>are each H, an alkyl or the like; R<SP>8</SP>is an alkyl or a haloalkyl; R<SP>9</SP>is an alkyl or a haloalkyl; X is O or S; and R<SP>10</SP>is an alkyl, a cycloalkyl, an alkenyl, an alkynyl, an alkoxy, an alkoxyalkyl or a haloalkoxy] and their salts, and use of them as the herbicide and/or the herbicidal effect-reinforcing agent are provided. <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

  The present invention relates to a novel jasmonic acid derivative, its use as a herbicide and herbicidal efficacy enhancer, and a method for producing the same.

Certain jasmonic acid derivatives have an effect as a plant growth promoter (for example, Patent Document 1), an effect as a flowering delaying agent for flower buds (for example, Patent Document 2), a crop growth regulator It is already known that the above-described action is exhibited (for example, Patent Document 3).
PCT International Publication WO 94/18833 Pamphlet JP 2003-335606 A JP 2003-335607 A

  However, in the above-mentioned documents, these derivatives have not been described at all as actions as herbicides and herbicidal efficacy enhancers.

  As a result of intensive studies to create a novel useful compound having a higher effect as a herbicide, the present inventors have obtained a novel jasmonic acid represented by the following formula (I) having excellent biological activity. Derivatives were found.

  Thus, the present invention provides compounds of formula (I):

式中、
Ｒ^１はアルキル又はアルケニルを示し、
Ｑは基

Where
R ¹ represents alkyl or alkenyl,
Q is group

を示し、
Ｒ^２、Ｒ^３、Ｒ^６及びＲ^７は、それぞれ独立して水素又はアルキルを示し、或いは
Ｒ^２はＲ^７と一緒になってエチレンを形成し、
Ｒ^４及びＲ^５は、それぞれ独立して水素又はアルキルを示すか、或いは結合している炭素原子と一緒になってＣ＝Ｏを示し、
Ｒ^８はアルキル又はハロアルキルを示し、
Ｒ^９はアルキル又はハロアルキルを示し、
ＸはＯ又はＳを示し、そして
Ｒ^１０はアルキル、シクロアルキル、アルケニル、アルキニル、アルコキシ、アルコキシアルキル又はハロアルコキシを示す、
で表されるジャスモン酸誘導体又はそれらの塩
を提供する。

Indicate
R ² , R ³ , R ⁶ and R ⁷ each independently represent hydrogen or alkyl, or R ² together with R ⁷ forms ethylene,
R ⁴ and R ⁵ each independently represent hydrogen or alkyl, or together with the carbon atoms to which they are attached, C═O;
R ⁸ represents alkyl or haloalkyl,
R ⁹ represents alkyl or haloalkyl,
X represents O or S, and R ¹⁰ represents alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkoxyalkyl or haloalkoxy,
A jasmonic acid derivative represented by the formula:

The jasmonic acid derivative represented by the above formula (I) has optical isomers derived from two adjacent asymmetric carbon atoms, and the side chain containing the group R ¹ and the group Q is a trans isomer. There may be antipodes (trans isomers) and cis isomers (cis isomers). Also, when R ¹ is alkenyl, EZ stereoisomers may exist. These compounds are all included in the formula (I) of the present invention.

  The compound of the formula (I) of the present invention can be synthesized, for example, by the following (a) or (b).

Production method (a): When Q represents a group (Q-1) Formula (II)

式中、
Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^４、Ｒ^５、Ｒ^６及びＲ^７は前記と同義である、
で表される化合物を塩基の存在下に転位反応させる方法。

Where
R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ are as defined above,
A rearrangement reaction of the compound represented by formula (I) in the presence of a base.

Production method (b): When Q represents a group (Q-2) or (Q-3), formula (III)

式中、
Ｒ^１は前記と同義であり、
Ｘはハロゲン、好ましくは塩素、臭素を示す、
で表される化合物を
式（ＩＶ）
Ｑ−Ｈ （ＩＶ）
式中、
Ｑは前記基（Ｑ−２）叉は（Ｑ−３）を示す、
で表される化合物と反応させる方法。

Where
R ¹ is as defined above,
X represents halogen, preferably chlorine or bromine,
A compound represented by formula (IV)
QH (IV)
Where
Q represents the group (Q-2) or (Q-3),
The method of making it react with the compound represented by these.

  The jasmonic acid derivative of formula (I) provided by the present invention surprisingly exhibits a strong herbicidal activity, in particular a fast-acting herbicidal action.

  In addition, according to the present invention, surprisingly, the jasmonic acid derivative of the formula (I) exhibits a strong herbicidal effect-enhancing action when mixed with a herbicidal compound, and in particular exhibits a herbicidal action itself. It shows a strong herbicidal synergistic effect.

In this specification,
“Alkyl” can be linear or branched, for example, C _1-6 alkyl, specifically methyl, ethyl, n- or iso-propyl, n— , Iso-, sec- or tert-butyl, n-pentyl, n-hexyl and the like.

  “Cycloalkyl” includes, for example, cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl and the like.

“Haloalkyl” refers to straight or branched chain alkyl in which at least one hydrogen is replaced by halogen, for example C _1-6 alkyl substituted by 1 to 6 fluoro, chloro and / or bromine. Specific examples thereof include 2,2,2-trifluoroethyl, 2,2,3,3,3-pentafluoropropyl, and the like.

“Alkoxy” refers to an alkyl-O— group in which the alkyl moiety has the above meanings, for example, C _1-6 alkoxy, specifically methoxy, ethoxy, n-propyloxy, isopropyloxy, and the like. It can be illustrated.

The haloalkyl moiety in the “haloalkoxy” may be the same as the above “haloalkyl”, for example, a C _1-6 haloalkoxy, specifically 2,2,2-trifluoroethyloxy, 2 2,3,3,3-pentafluoropropyloxy and the like.

“Alkenyl” may be linear or branched, and may represent, for example, C _2-6 alkenyl, specifically, allyl, 2-butenyl, 3-butenyl, isobutenyl, 1- Examples include pentenyl, trans-2-pentenyl, cis-2-pentenyl, 3-pentenyl, 4-pentenyl, 2-hexenyl, 3-hexenyl, 5-hexenyl, 3-methyl-2-pentenyl and the like.

“Alkynyl” can be linear or branched, for example, can represent C _3-6 alkynyl, specifically illustrating propargyl, 3-butynyl, 5-hexynyl, and the like. Can do.

  The “salt” in the “jasmonic acid derivative or a salt thereof” can be an organic salt or an inorganic salt, such as a tertiary amine salt, an alkali metal salt or an alkaline earth metal salt, specifically, And salts of triethylamine, diisopropylethylamine, triethanolamine, sodium, potassium and the like.

  A “fast-acting herbicide” refers to a herbicidal active compound that exhibits a herbicidal effect within a few hours at the latest after application.

  The term “herbicidal efficacy enhancer” refers to a compound that exhibits a herbicidal efficacy after mixing that exceeds the addition of individual herbicidal efficacy by mixing with other herbicides, regardless of whether or not the compound itself has herbicidal efficacy. Say.

In the compound of the formula (I), more preferably,
R ¹ represents C _1-6 alkyl or C _2-6 alkenyl,
Q is based

を示し、
Ｒ^２、Ｒ^３、Ｒ^６及びＲ^７が、それぞれ独立して水素又はＣ_１−６アルキルを示し、或いは
Ｒ^２がＲ^７と一緒になってエチレンを形成し、
Ｒ^４及びＲ^５が、それぞれ独立して水素又はＣ_１−６アルキルを示すか、或いは結合している炭素原子と一緒になってＣ＝Ｏを示し、
Ｒ^８がＣ_１−６アルキル又はＣ_１−６ハロアルキルを示し、
Ｒ^９がＣ_１−６アルキル又はＣ_１−６ハロアルキルを示し、
ＸがＯ又はＳを示し、そして
Ｒ^１０がＣ_１−６アルキル、Ｃ_３−７シクロアルキル、Ｃ_３−６アルケニル、Ｃ_３−６アルキニル、Ｃ_１−６アルコキシ、Ｃ_１−４アルコキシＣ_１−４アルキル又はＣ_１−６ハロアルコキシを示す。

Indicate
R ² , R ³ , R ⁶ and R ⁷ each independently represent hydrogen or C _1-6 alkyl, or R ² together with R ⁷ forms ethylene,
R ⁴ and R ⁵ each independently represent hydrogen or C _1-6 alkyl, or together with the carbon atoms to which they are attached, C═O;
R ⁸ represents C _1-6 alkyl or C _1-6 haloalkyl,
R ⁹ represents C _1-6 alkyl or C _1-6 haloalkyl,
X represents O or S, and R ¹⁰ is C _1-6 alkyl, C _3-7 cycloalkyl, C _3-6 alkenyl, C _3-6 alkynyl, C _1-6 alkoxy, C _1-4 alkoxyC _{1 -4} an alkyl or _{C 1-6} haloalkoxy.

In the compound of the formula (I), particularly preferably
R ¹ represents butyl, pentyl, hexyl or 2-pentenyl,
Q is based

を示し、
Ｒ^２、Ｒ^３、Ｒ^６及びＲ^７が、それぞれ独立して水素又はメチルを示し、或いは
Ｒ^２がＲ^７と一緒になってエチレンを形成し、
Ｒ^４及びＲ^５が、それぞれ独立して水素又はメチルを示すか、或いは結合している炭素原子と一緒になってＣ＝Ｏを示し、
Ｒ^８がメチル叉はエチルを示し、
Ｒ^９がメチル、エチル又は２，２，２−トリフルオロエチルを示し、
ＸがＯ又はＳを示し、そして
Ｒ^１０がエチル、シクロプロピル、アリル、４−ペンテニル、５−ヘキセニル、プロパルギル、５−ヘキシニル、エトキシ、２−メトキシエチル、２−エトキシエチル、２，２，２−トリフルオロエチルオキシ又は２，２，３，３，３−ペンタフルオロプロピルオキシを示す。

Indicate
R ² , R ³ , R ⁶ and R ⁷ each independently represent hydrogen or methyl, or R ² together with R ⁷ forms ethylene,
R ⁴ and R ⁵ each independently represent hydrogen or methyl, or together with the carbon atoms to which they are attached, C═O;
R ⁸ represents methyl or ethyl,
R ⁹ represents methyl, ethyl or 2,2,2-trifluoroethyl,
X represents O or S, and R ¹⁰ is ethyl, cyclopropyl, allyl, 4-pentenyl, 5-hexenyl, propargyl, 5-hexynyl, ethoxy, 2-methoxyethyl, 2-ethoxyethyl, 2,2,2 -Represents trifluoroethyloxy or 2,2,3,3,3-pentafluoropropyloxy.

  In the production method (a), for example, 1- (2-pentyl-3-oxo-cyclopentyl) acetoxy-2-cyclohexen-3-one and, for example, 4-dimethylaminopyridine as a base are used as raw materials. It is represented by the following reaction formula.

  When the production method (b) uses, for example, 1,3-dimethylbarbituric acid, (2-pentyl-3-oxo-cyclopentyl) acetyl chloride as a raw material and, for example, triethylamine as a base, the following reaction formula is used. Represented.

  The compound of the above formula (I), when Q represents a group (Q-1), is represented by the formula (Ia), (Ib), (Ic) and (Id), and Q is a group ( In the case of Q-2), as shown in formulas (Ie), (If), (Ig) and (Ih), and in the case where Q represents a group (Q-3), in formula (Ii) ), (Ij) and (Ik), can exist as tautomers.

  In this specification, as representative examples, they are represented by the structures of formula (Ia), formula (Ie) and formula (Ii), respectively, but the compounds of formula (I) are represented by (Ib), (Ic), ( Also included are compounds of Id), (If), (Ig), (Ih), (Ij) and (Ik).

  The compound of the formula (II) used as a starting material in the production method (a) is a novel compound not described in conventional literatures, for example, JP-A-2-173, JP-A-2-222, According to the method described in any one of Kaihei 2-6425, for example, a formula

式中、
Ｒ^２、Ｒ^３、Ｒ^４、Ｒ^５、Ｒ^６及びＲ^７は前記と同義である、
で表される化合物を、前記式（ＩＩＩ）の化合物と反応させることにより容易に製造することができる。

Where
R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ are as defined above.
Can be easily produced by reacting the compound represented by formula (III) with the compound of the formula (III).

  The compound of the above formula (V) is available as a commercial product, or can be produced according to the method described in JP-A-9-309883, European Patent Office No. 283162, and the like.

  The compound of the above formula (III) is a compound known per se and can be produced, for example, according to the method described in PCT International Publication WO 94/18833.

Typical examples of the compound of the formula (II) used as a raw material in the production method (a) include the following.
1- (2-pentyl-3-oxo-cyclopentyl) acetoxy-cyclohexen-3-one,
1- {2- (2-penten-1-yl) -3-oxo-cyclopentyl} -acetoxy-cyclohexen-3-one,
4-methyl-1- (2-pentyl-3-oxo-cyclopentyl) acetoxy-cyclohexen-3-one,
4-methyl-1- {2- (2-penten-1-yl) -3-oxo-cyclo-pentyl} acetoxy-cyclohexen-3-one,
4,4-dimethyl-1- (2-pentyl-3-oxo-cyclopentyl) -acetoxy-cyclohexen-3-one,
4,4-dimethyl-1- {2- (2-penten-1-yl) -3-oxo-cyclopentyl} acetoxy-cyclohexen-3-one,
5-methyl-1- (2-pentyl-3-oxo-cyclopentyl) acetoxy-cyclohexen-3-one,
5-methyl-1- {2- (2-penten-1-yl) -3-oxo-cyclo-pentyl} acetoxy-cyclohexen-3-one,
5,5-dimethyl-1- (2-pentyl-3-oxo-cyclopentyl) -acetoxy-cyclohexen-3-one,
5,5-dimethyl-1- {2- (2-penten-1-yl) -3-oxo-cyclopentyl} acetoxy-cyclohexen-3-one,
4,4,6,6-tetramethyl-1- (2-pentyl-3-oxo-cyclo-pentyl) acetoxy-cyclohexene-3,5-dione,
4,4,6,6-tetramethyl-1- {2- (2-penten-1-yl) -3-oxo-cyclopentyl} acetoxy-cyclohexene-3,5-dione,
4-Oxo-2- (2-pentyl-3-oxo-cyclopentyl) acetoxy-bicyclo [3.2.1. ] Oct-2-ene,
4-Oxo-2- {2- (2-penten-1-yl) -3-oxo-cyclo-pentyl} acetoxy-bicyclo [3.2.1. ] Oct-2-ene, etc.

The compound of the formula (III) used as a raw material in the said manufacturing method (b) is a compound known per se, and can illustrate the following.
(2-n-butyl-3-oxo-cyclopentyl) acetyl chloride,
(2-pentyl-3-oxo-cyclopentyl) acetyl chloride,
(2-n-hexyl-3-oxo-cyclopentyl) acetyl chloride,
(2-pentyl-3-oxo-cyclopentyl) acetyl chloride,
{2- (2-penten-1-yl) -3-oxo-cyclopentyl} acetyl-chloride,
{2- (2-penten-1-yl) -3-oxo-cyclopentyl} acetyl-chloride,
{2- (1-penten-1-yl) -3-oxo-cyclopentyl} acetyl-chloride,
{2- (3-penten-1-yl) -3-oxo-cyclopentyl} acetyl-chloride,
{2- (4-penten-1-yl) -3-oxo-cyclopentyl} acetyl-chloride,
{2- (2-hexen-1-yl) -3-oxo-cyclopentyl} acetyl-chloride,
{2- (3-hexen-1-yl) -3-oxo-cyclopentyl} acetyl-chloride,
{2- (5-hexen-1-yl) -3-oxo-cyclopentyl} acetyl-chloride,
{2- (3-Methyl-2-penten-1-yl) -3-oxo-cyclopentyl} acetyl chloride, and the like.

The compound of formula (IV) used as a raw material in the production method (b) is a compound known per se,
When Q represents a group (Q-2), for example, Chemische Berichte, Vol. 49, p. 652, 1916, Journal of the American Chemical Society, Vol. 73, p. 5326-5332, 1951, US Pat. No. 5,674,870, Journal of Heterocyclic Chemistry, Vol. 18, p. 1095-1100, 1981, can be produced according to the method described in any of JP-A-63-1121828,
When Q represents a group (Q-3), for example, Chemische Berichte, Vol. 115 (1), p. 355-380 (1982), Journal of Organic Chemistry, Vol. 23, p. 835-837 (1958), Justus Liebigs Analender der Chemie, No. 185, 12, p. 1946-1962 (1978), Synthetic Communications, Vol. 17 (10), p. 1189-1198 (1987) and the like.

  Typical examples of the compound of formula (IV) used as a raw material in the production method (b) include the following.

1,3-dimethylbarbituric acid,
1,3-dimethyl-2-thiono-barbituric acid,
1-ethyl-3-methyl-barbituric acid,
1-ethyl-3-methyl-2-thiono-barbituric acid,
1-methyl-3- (2,2,2-trifluoroethyl) -barbituric acid,
1-methyl-3- (2,2,2-trifluoroethyl) -2-thiono-barbituric acid,
1,3-bis- (2,2,2-trifluoroethyl) -barbituric acid,
1,3-bis- (2,2,2-trifluoroethyl) -2-thiono-barbituric acid,
3-ethyl-3-oxopropanenitrile,
3-cyclopropyl-3-oxopropanenitrile,
3-isopropyl-3-oxopropanenitrile,
3- {4-penten-1-yl} -3-oxopropanenitrile,
3- {5-hexen-1-yl} -3-oxopropanenitrile,
3- {5-hexyn-1-yl} -3-oxopropanenitrile,
Methyl cyanoacetate,
Ethyl cyanoacetate,
Propyl cyanoacetate,
Isopropyl cyanoacetate,
Allyl cyanoacetate,
Propargyl cyanoacetate,
Methoxyethyl cyanoacetate,
Ethoxyethyl cyanoacetate,
Cyanoacetic acid 2,2,2-trifluoroethyl,
Cyanoacetic acid 2,2,3,3,3-pentafluoropropyl, and the like.

  The reaction of the above production method (a) can be carried out in a suitable diluent. Examples of the diluent used here include: aliphatic, cycloaliphatic and aromatic hydrocarbons (optionally chlorine). For example, pentane, hexane, cyclohexane, petroleum ether, ligroin, benzene, toluene, dichloromethane, chloroform, 1,2-dichloroethane, etc .; ethers such as ethyl ether, methyl ethyl ether, isopropyl ether, Butyl ether, dioxane, dimethoxyethane (DME), tetrahydrofuran (THF) and the like; ketones such as acetone, methyl ethyl ketone (MEK), methyl-isopropyl ketone, methyl isobutyl ketone (MIBK) and the like; nitriles such as acetonitrile, propio Nitrile etc. Esters such as ethyl acetate, amyl acetate and the like; bases include, for example, pyridine, and the like.

  The production method (a) can be carried out in the presence of a base. Examples of the base include organic bases and pyridines such as 4-dimethylaminopyridine (DMAP).

  The production method (a) can be carried out in the presence of a cyanide and a tertiary amine. Examples of the cyanide include sodium cyanide, potassium cyanide, acetone cyanohydrin, hydrogen cyanide and the like. Examples of tertiary amines include triethylamine.

  When the production method (a) is carried out in the presence of cyanide, a phase transfer catalyst can be used in combination. Examples of the phase transfer catalyst used in this case include crown ethers such as dibenzo-18-crown-6, dicyclohexyl-18-crown-6, and 18-crown-6.

  When a phase transfer catalyst is used, the reaction can be carried out in the presence of a diluent. Examples of the diluent used in this case include water; aliphatic, cycloaliphatic and aromatic hydrocarbons. (May be chlorinated in some cases), for example, pentane, hexane, cyclohexane, petroleum ether, ligroin, benzene, toluene, dichloromethane, etc .; ethers such as ethyl ether, methyl ethyl ether, isopropyl ether, butyl ether, dioxane , Dimethoxyethane (DME), tetrahydrofuran (THF), diethylene glycol dimethyl ether (DGM) and the like; nitriles such as acetonitrile and propionitrile.

  Process (a) can be carried out within a substantially wide temperature range, but it is generally preferred to carry out at a temperature within the range of about 0 to about 180 ° C, particularly about 20 to about 150 ° C. In addition, the reaction is desirably performed under normal pressure, but in some cases, the reaction can be performed under pressure or reduced pressure.

  In carrying out the process (a), for example, by reacting 1 mol of the compound of formula (II) in the presence of 0.1 to 3 mol of 4-dimethylaminopyridine in a diluent, for example toluene. A compound can be obtained.

  When process (a) is carried out in the presence of cyanide, the reaction temperature can generally be in the range of about −10 to about 80 ° C., preferably about 5 to about 50 ° C. In addition, the reaction is desirably performed under normal pressure, but in some cases, the reaction can be performed under pressure or reduced pressure.

  In carrying out process (a) in the presence of cyanide, for example, 1 mol of a compound of formula (II) in a diluent, for example acetonitrile, is used as a 1 to 4 mol amount of triethylamine and cyanide, for example 0.01. The target compound can be obtained by reacting in the presence of ˜1 molar amount of acetone cyanohydrin.

  In carrying out the production method (a), starting from the compounds of the formulas (III) and (V), the reaction of the compound of the formula (I) is carried out continuously without isolating the compound of the formula (II). Obtainable.

  The reaction of the above production method (b) can be carried out in a suitable diluent, and examples of the diluent used in this case include aliphatic, cycloaliphatic and aromatic hydrocarbons (optionally chlorine). Ethers such as dioxane, dimethoxyethane (DME), tetrahydrofuran (THF), etc .; nitriles such as acetonitrile, propionitrile, etc .; bases such as benzene, toluene, xylene, etc. , Pyridine and the like.

  The production method (b) can be carried out in the presence of an acid binder. Examples of the acid binder include hydrides or carbonates of alkali metals and alkaline earth metals as inorganic bases, such as sodium hydride. Lithium hydride, sodium carbonate, potassium carbonate, calcium carbonate, etc .; for example, alcoholates, tertiary amines, dialkylaminoanilines and pyridines as organic bases, such as potassium tert-butoxide, triethylamine, tri-n-propyl Amine, tri-n-butylamine, ethyldiisopropylamine, 1,1,4,4-tetramethylethylenediamine (TMEDA), N, N-dimethylaniline, N, N-diethylaniline, pyridine, 4-dimethylaminopyridine (DMAP) ), 1,4-diazabicyclo [2.2.2] oct (DABCO), 1,5-diazabicyclo [4.3.0] nonene-5 (DBN), 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU), and the like. .

  The production method (b) can be carried out within a substantially wide temperature range.

  In general, it can be carried out between about -70 to about 200 ° C, preferably between about -50 and about 100 ° C. In addition, the reaction is desirably performed under normal pressure, but can be operated under pressure or reduced pressure.

  In carrying out the production method (b), for example, 0.5 mol to 1.5 mol of a compound of formula (IV) in a diluent such as tetrahydrofuran is added to triethylamine with respect to 1 mol of a compound of formula (III). The target compound can be obtained by reacting in the presence.

  The active compound of the formula (I) of the present invention exhibits excellent herbicidal activity against various weeds as shown in the biological test examples described later, and can be used as a herbicide. As used herein, weed means all plants that grow in undesirable places in a broad sense. The compounds of the invention act as non-selective herbicides depending on the concentration used. The active compounds of formula (I) according to the invention can be used, for example, against the following weeds.

Genus of dicotyledonous weeds : Sinapis, Capsella, Beanidum, Lepidium, Galium, Stellaria, Chenopodium, tuna ), Hangonso Noborgiku Kion (Senecio), Amaranthus, Surihiyu Matsuba Button (Portulaca), Xanathium (Ipomoea), Polyganza A Circium, Sonchus, Eggplant potato (Solanum), Inugarashi (Rorip) a), Laminum, Stag beetle (Veronica), Datura (Dura), Violet, Violet, Galeopsis, Papaver, Centaurea (Rotala), Azena (Lindernia), American horned phoenix (Sesbania), white clover (Trifolium), Ibibi (Abutilon), Photonosa (Lamium), dog chamomile (Matricia), mugwort (Arte), dogwood (Arte)

The genus of monocotyledonous weeds : Echinochloa, Enokoro Awa (Setaria), Millet (Panicum), Digitaria, Ayugaeri Timothy (Phlum), Strawberry Tuna Suzumenokatabira (Poa), Ushikokesa Tobo Ohishiba Shikokubie (Eleuusine), Dokumugi (Lolium), Swan-growth Inumugi (Bromus), Oats oats (Ovena) (Avena), Cyperus papyrus shichitoui hamasuge (Cyper), Moro-g Konogi (Monochoria), Tentsuki (Fimbristylis), Omodaka Kwai (Sagittaria), Hariy Ku Guwai (Eleocharis), bulrush, Ukiyagura-thick (Scirpus), Paspalum (Paspalum), platypus (Ischaemum), Agrostis (Agrostis), foxtail (Alopecurus), bermudagrass (Cynodon), dayflower (Commelina) and the like.

Other weeds : Eguisatum, etc.

  The active compounds of the formula (I) according to the invention are used as non-selective herbicides, for example, dormant fields of cultivated plants, fallow land, before plowing, before sowing, before planting or before planting, Industrial lands such as shores, fields, fields after harvesting, factories, railroad tracks, roads, parking lots, parks, gardens, dams, playgrounds, residential land, cemeteries, slopes, pastures, grasslands, plantations, non-forests Etc. can be used.

  The active compound of formula (I) of the present invention is a perennial plant cultivation, for example, afforestation, ornamental plantation, orchard, vineyard, citrus orchard, nut orchard, banana plantation, coffee plantation, tea plantation, It can be used for undergrowth control such as rubber plantation, Guinea oil palm plantation, cocoa plantation, orchard, hop plantation.

  The active compound of the formula (I) of the present invention also grows and proliferates in water systems such as gardens, trees, grasslands, golf courses, artificial grass, concrete, road surfaces, beaches, rivers, lakes, paddy fields, etc. It shows excellent control effect (herbicidal activity) against algae and bryophytes (moss) harmful to these landscapes and uses, and can be used as a control agent (herbicide) against algae and bryophytes (moss) it can. Algae and bryophytes (moss) that can be controlled by the active compounds of formula (I) of the present invention include, for example, Antitrichia, Bryum, Barbulavineealis, Dendroalsia, Dicknoweuumia, Didymodon, Homathecium, Homathecium, Homathecium, , Tortula, Zygodon, Marcheantia, Conocephalum, Proellaroelliii, Porella, Oscillatoria, Euglena, Chlamydomonas, Chlorella, Ulothrix, Monomastix, Tabella It can be mentioned.

The active compound of the formula (I) of the present invention can exhibit a more powerful synergistic herbicidal action as a mixed herbicide composition with other herbicides, for example, known herbicides (generic names) exemplified below.
Sulfonylurea herbicides: for example, chlorsulfuron, sulfometuron methyl, chlorimuron ethyl, triasulfuron, amidosulfuron, oxasulfuron, tribenuron ethyl, prosulfuron, etamethsulfuron methyl, triflusulfuron Methyl, thifensulfuron methyl, frazasulfuron, rimsulfuron, nicosulfuron, flupirsulfuron, bensulfuron methyl, pyrazosulfuron ethyl, foramsulfuron, sulfosulfuron, synosulfuron, azimusulfuron, metsulfuron methyl, halosulfuron methyl , Ethoxysulfuron, cyclosulfamuron, iodosulfuron, etc .;
Carbamate herbicides: for example, fenmedifam, chloroprofam, ashram, beniocarb, molinate, esprocarb, piributicalbu, dimethylpiperate, swep, etc .;
Chloroacetanilide herbicides: for example, propachlor, metazachlor, alachlor, acetochlor, metolachlor, butachlor, pretilachlor, tenyl chlor, etc .;
Diphenyl ether herbicides: for example, acifluorfen, oxyfluorfen, lactofen, fomesafen, aclonifen, clomethoxynil, bifenox, CNP, etc .;
Triazine herbicides: for example, simazine, atrazine, propazine, cyanazine, amethrin, simethrin, dimetamethrin, promethrin, etc .;
Phenoxy acid or benzoic acid herbicide: for example, 2,3,6-TBA, dicamba, quinclolac, kimmelac, clopyralid, picloram, triclopyr, fluroxypyr, phenoxaprop, diclohopmethyl, fluazifopbutyl, haloxy Hop methyl, quizalofop ethyl, cyhalo hop butyl, 2,4-PA, MCP, MCPB, phenothiol, etc .;
Acid amide or urea herbicides: for example, isoxaben, diflufenican, diuron, linuron, fluometuron, diphenoxuron, methyl dimuron, isoproturon, isouron, tebuthiuron, metabenzothiauron, propanil, mefenacet, clomeprop, naproanilide, bromobutide , Cumyluron, ettobenzanide, oxadichrome mephone, etc .;
Organophosphorus herbicides: for example, glyphosate, bialaphos, glufosinate, amiprophos methyl, anilophos, bensulide, piperofos, butamifos;
Dinitroaniline herbicides: for example, trifluralin, prodiamine, etc .;
Cyclohexanedione herbicides: for example, alloxidim, cetoxydim, cloproxidim, cresodymium, cycloxydim, tolalkoxydim, etc .;
Imidazolinone herbicides: for example, imazametabenz, imazapill, imazametapill, imazetapill, imazamox, imazaquin, etc .;
Bipyridium herbicides: for example, paraquat, diquat, etc .;
Carbamoyltetrazolinone herbicides: for example, fentolazamide and the like;
Phenolic herbicides: for example, bromoxynyl, ioxinyl, dinosebu, etc .;
Other herbicides: for example, bentazone, tridiphan, indanophan, amitrole, carfentrazone ethyl, sulfentrazone, fenchlorazole ethyl, isoxaflutole, cromazone, maleic acid hydrazide, pyridate, chloridazone, norflurazon, pyrithiobac, Bromasil, Turbacil, Metrivudine, Cinmethylin, Full microlacpentyl, Flumioxazin, Fluthiacetmethyl, Azaphenidine, Benfrate, Oxadiazone, Oxadiargyl, Pentoxazone, Cavenstrol, Pyriminovac, Bispyribac sodium, Pyribenzoxime, Pyriphthalide, Piraflufenethyl, Benzobicyclo , Dithiopyr, darapon, chlorthiamide, pelargonic acid, cyclobenenyl and the like.

In the herbicides exemplified above, preferably,
Sulfomethulone methyl, phenmedifam, ashram, oxyfluorfen, simazine, atrazine, amethrin, promethrin, triclopyr, phenoxaprop, fluazifopbutyl, 2,4-PA, MCP, isoxaben, diuron, linuron, isouron, tebuthiuron , Propanyl, glyphosate, bialaphos, glufosinate, amiprophosmethyl, bromoxynyl, ioxynyl, trifluralin, cetoxidim, imazapyr, paraquat, diquat, fentrazamide, bentazone, amitrol, carfentrazone ethyl, pyridate, bromacil, terbacyl, metlibudine, flumioxazine Oxadiazone, oxadiargyl, bispyribac sodium, pyraflufenethyl .

  The active compound is a known herbicide described in “Pesticide Manual”, 2000, published by British Crop Protect Council.

  The mixing ratio of the compound of formula (I) as the herbicide of the present invention and the known herbicide can be varied over a wide range depending on the purpose of use and the like.

For example, per part by weight of the compound of formula (I) of the present invention,
The sulfonylurea herbicide is 0.00001 to 1 part by weight, preferably 0.0001 to 0.1 part by weight,
The carbamate herbicide is 0.001 to 10 parts by weight, preferably 0.01 to 1 part by weight,
The chloroacetanilide herbicide is 0.001 to 10 parts by weight, preferably 0.01 to 1 part by weight,
The diphenyl ether herbicide is 0.0001 to 10 parts by weight, preferably 0.001 to 1 part by weight,
The triazine herbicide is 0.005 to 50 parts by weight, preferably 0.05 to 5 parts by weight,
The phenoxy acid or benzoic acid herbicide is 0.001 to 10 parts by weight, preferably 0.01 to 1 part by weight,
The acid amide or urea herbicide is 0.001 to 20 parts by weight, preferably 0.01 to 2 parts by weight,
The organophosphorus herbicide is 0.005 to 50 parts by weight, preferably 0.05 to 5 parts by weight,
The dinitroaniline herbicide is 0.005 to 50 parts by weight, preferably 0.05 to 5 parts by weight,
The cyclohexanedione herbicide is 0.0005 to 0.5 parts by weight, preferably 0.05 to 0.5 parts by weight,
The imidazolinone herbicide is 0.0001-5 parts by weight, preferably 0.001-0.5 parts by weight,
The bipyridium herbicide is 0.005 to 30 parts by weight, preferably 0.05 to 3 parts by weight,
The carbamoyltetrazolinone herbicide is 0.001 to 3 parts by weight, preferably 0.01 to 0.3 parts by weight,
Other herbicides, for example
Bentazone is 0.005 to 10 parts by weight, preferably 0.05 to 1 part by weight,
Amitrol is 0.01 to 1 part by weight, preferably 0.1 to 1 part by weight,
The carfentrazone ethyl is 0.001 to 1 part by weight, preferably 0.005 to 0.1 part by weight,
The pyridate is 0.005 to 20 parts by weight, preferably 0.05 to 2 parts by weight,
Bromasil is 0.001 to 10 parts by weight, preferably 0.01 to 1 part by weight,
Turbacil is 0.02 to 20 parts by weight, preferably 0.02 to 2 parts by weight,
Metribuzin is 0.0005 to 20 parts by weight, preferably 0.005 to 2 parts by weight,
Flumioxazin is 0.0005 to 1 part by weight, preferably 0.005 to 0.1 part by weight,
Oxadiazone is 0.005 to 20 parts by weight, preferably 0.05 to 2 parts by weight,
Oxadialgyl is 0.0005 to 1 part by weight, preferably 0.005 to 0.1 part by weight,
Bispyribac sodium is 0.0001-1 part by weight, preferably 0.001-0.1 part by weight,
Pyraflufenethyl can be used in the range of 0.00005 to 0.5 parts by weight, preferably 0.0001 to 0.05 parts by weight.

  The active compound of formula (I) of the present invention can be used as a herbicidal efficacy enhancer by adding to other herbicides, for example, the known herbicides (generic names) exemplified above, to enhance their herbicidal efficacy. it can.

The mixing ratio of the compound of formula (I) as a herbicidal efficacy enhancer of the present invention and a known herbicide can be varied over a wide range depending on the purpose of use. For example, per part by weight of the compound of formula (I) of the present invention,
The sulfonylurea herbicide is 0.0001 to 10 parts by weight, preferably 0.001 to 1 part by weight,
The carbamate herbicide is 0.01 to 100 parts by weight, preferably 0.1 to 10 parts by weight,
The chloroacetanilide herbicide is 0.01 to 100 parts by weight, preferably 0.1 to 10 parts by weight,
The diphenyl ether herbicide is 0.001 to 100 parts by weight, preferably 0.01 to 10 parts by weight,
The triazine herbicide is 0.05 to 500 parts by weight, preferably 0.5 to 50 parts by weight,
The phenoxy acid or benzoic acid herbicide is 0.01 to 100 parts by weight, preferably 0.1 to 10 parts by weight,
The acid amide or urea herbicide is 0.01 to 200 parts by weight, preferably 0.1 to 20 parts by weight,
The organophosphorus herbicide is 0.05 to 500 parts by weight, preferably 0.5 to 50 parts by weight,
The dinitroaniline herbicide is 0.05 to 500 parts by weight, preferably 0.5 to 50 parts by weight,
The cyclohexanedione herbicide is 0.005 to 5 parts by weight, preferably 0.05 to 5 parts by weight,
The imidazolinone herbicide is 0.001 to 50 parts by weight, preferably 0.01 to 5 parts by weight,
The bipyridium herbicide is 0.05 to 300 parts by weight, preferably 0.5 to 30 parts by weight,
The carbamoyltetrazolinone herbicide is 0.01 to 30 parts by weight, preferably 0.1 to 3 parts by weight,
Other herbicides, for example
Bentazone is 0.05 to 100 parts by weight, preferably 0.5 to 10 parts by weight,
Amitrol is 0.001 to 10 parts by weight, preferably 0.01 to 1 part by weight,
Carfentrazone ethyl is 0.001 to 10 parts by weight, preferably 0.01 to 0.1 parts by weight,
The pyridate is 0.05 to 200 parts by weight, preferably 0.5 to 20 parts by weight,
Bromasil is 0.01 to 100 parts by weight, preferably 0.1 to 10 parts by weight,
Turbacil is 0.02 to 200 parts by weight, preferably 0.2 to 20 parts by weight,
Metribuzin is 0.005 to 200 parts by weight, preferably 0.05 to 20 parts by weight,
Flumioxazin is 0.005 to 10 parts by weight, preferably 0.05 to 1 part by weight,
Oxadiazone is 0.05 to 200 parts by weight, preferably 0.5 to 20 parts by weight,
Oxadialgyl is 0.005 to 10 parts by weight, preferably 0.05 to 1 part by weight,
Bispyribac sodium is 0.001 to 10 parts by weight, preferably 0.01 to 1 part by weight,
Pyraflufenethyl can be used in the range of 0.0005 to 5 parts by weight, preferably 0.005 to 0.5 parts by weight.

  The compound of the formula (I) of the present invention, as shown in the biological test examples described later, has an unexpectedly enhanced herbicidal effect when added to a known herbicide, and as a result, exhibits excellent herbicidal activity against various weeds. Can be used as a herbicidal efficacy enhancer.

  The active compounds of the formula (I) according to the invention can be in the usual pharmaceutical forms. Examples of the preparation form include liquids, wettable powders, emulsions, suspensions, powders, granular wettable powders, tablets, granules, concentrated suspension emulsions, microcapsules in polymers, jumbo drugs, and the like. Can be mentioned.

  These preparations can be produced by a method known per se. Such a process may be prepared, for example, by mixing the active compound with a developing agent, ie a liquid or solid diluent or carrier, and optionally a surfactant, ie an emulsifier and / or a dispersant. it can.

  Examples of the liquid diluent or carrier include aromatic hydrocarbons (for example, xylene, toluene, alkylnaphthalene, etc.), chlorinated aromatic or chlorinated aliphatic hydrocarbons (for example, chlorobenzenes, ethylene chloride, chloride) Methylene etc.), aliphatic hydrocarbons [eg cyclohexane etc., paraffins (eg mineral oil fraction etc.)], alcohols (eg butanol, glycol etc.) and their ethers, esters etc., ketones (eg acetone) , Methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.), strong polar solvents (for example, dimethylformamide, dimethyl sulfoxide, etc.), water and the like. When water is used as a developing agent, for example, an organic solvent can be used as an auxiliary solvent.

  Solid diluents or carriers include, for example, ground natural minerals (eg, kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite, diatomaceous earth, etc.), ground synthetic minerals (eg, highly dispersed silicic acid, alumina, silicic acid) Salt). Solid carriers for granules include crushed and separated rocks (eg, calcite, marble, pumice, foamstone, dolomite, etc.), synthetic grains of inorganic and organic powders, organic substances (eg sawdust, coconut palm) Corn, corn cobs, tobacco stems, etc.).

  Examples of the emulsifier include nonionic and anionic emulsifiers [for example, polyoxyethylene fatty acid ester, polyoxyethylene fatty acid alcohol ether (for example, alkylaryl polyglycol ether, alkylsulfonate, alkylsulfate, arylsulfonate, etc. )], Albumin hydrolysis products.

  Examples of the dispersant include lignin sulfite waste liquid and methylcellulose.

  Fixing agents can also be used in preparations (powder, granules, emulsions), and examples of the fixing agent include carboxymethyl cellulose, natural and synthetic polymers (for example, gum arabic, polyvinyl alcohol, polyvinyl acetate, etc.). be able to.

  Colorants can also be used. Examples of the colorants include inorganic pigments (eg, iron oxide, titanium oxide, Prussian blue, etc.), alizarin dyes, organic dyes such as azo dyes or metal phthalocyanine dyes, and iron, manganese. And trace elements such as salts of metals such as boron, copper, cobalt, molybdenum, and zinc.

  The preparation can generally contain 1 to 95% by weight, preferably 5 to 90% by weight, of the active ingredient of the formula (I) as a herbicide.

  The active compound of the formula (I) of the present invention can be used directly as it is, in the above-mentioned preparation form, or in a use form prepared by further diluting, and a known herbicide It can also be used as a mixed composition. As described above, such a mixed composition can be used in the form of a preparation in advance, or can be used by tank-mixing each component at the time of application. And as an application method, liquid agent watering (spraying atomizing), spraying, etc. can be illustrated, for example.

  The active compounds and mixed compositions of formula (I) according to the invention can be used at any stage before and after germination of plants.

  The application rates as active herbicides of the active compounds of the formula (I) according to the invention can be varied within a substantial range. It is fundamentally different depending on the nature of the effect to be desired. The application rate is generally about 0.5 to about 20 kg, preferably about 1 to about 5 kg of the active compound of the formula (I) as a herbicide per hectare.

  The addition amount (application rate) of the active compound of the formula (I) according to the invention as a herbicidal efficacy enhancer can be varied within a substantial range. It is fundamentally different depending on the nature of the effect to be desired. The added amount (application amount) is generally about 0.05 to about 5 kg, preferably about 0.1 to about 1 kg of active compound of formula (I) as a herbicidal efficacy enhancer, for example, per hectare. Can be illustrated.

  Next, the production and use of the compounds of the present invention will be more specifically shown by the following examples, but the present invention should not be limited to these.

<Production Example of Compound>
Synthesis example 1

1- (2-pentyl-3-oxo-cyclopentyl) acetoxy-2-cyclohexen-3-one (cis isomer) (3.06 g) was dissolved in toluene (60 ml), and DMAP (1.47 g) was added to this solution. In addition, the mixture was heated to reflux for 5 hours. After cooling, the mixture was washed with dilute hydrochloric acid and then with saturated saline and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The crude product was purified by silica gel column chromatography (elution solvent ether: hexane = 1: 3) to obtain the desired 2- (2-pentyl-3-oxo-cyclopentyl) acetyl-1,3-cyclohexanedione (cis form). (2.35 g) was obtained.
n ^D ₂₄ 1.5140.

Synthesis example 2

To a solution of 1,3-dimethylbarbituric acid (1.72 g) and triethylamine (2.43 g) in THF (60 ml), (2-pentyl-3-oxo-cyclopentyl) acetyl chloride (cis form) (2.31 g) Of THF (20 ml) was added dropwise at 0 ° C., followed by stirring at room temperature for 12 hours. Triethylamine hydrochloride was filtered off, and the filtrate was concentrated under reduced pressure. The residue was made weakly acidic by adding dilute hydrochloric acid, extracted with ethyl acetate (50 ml), dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The crude product was purified by silica gel column chromatography (elution solvent ether: hexane = 1: 5) to obtain the desired 5- (2-pentyl-3-oxo-cyclopentyl) acetyl-1,3-dimethylbarbituric acid (cis Body) (2.57 g).
n _D ²⁰ 1.5325.

Synthesis example 3

To a sodium hydride (60% oiliness: 1.26 g) suspended in THF (40 ml), a solution of 3-cyclopropyl-3-oxopropanenitrile (1.72 g) in THF (20 ml) was added dropwise at 0 ° C. . The mixture was further stirred at this temperature for 30 minutes. Next, a THF (20 ml) solution of (2-pentyl-3-oxo-cyclopentyl) acetyl chloride (cis form) (3.46 g) is added dropwise at -70 ° C. Thereafter, the mixture was stirred at the same temperature for 30 minutes, and further stirred at room temperature for 12 hours. The reaction solution was concentrated under reduced pressure, a small amount of water was added to the residue, and the aqueous layer was washed with ether (20 ml). The aqueous layer was made weakly acidic with dilute hydrochloric acid, extracted with ethyl acetate (100 ml), dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The crude product was purified by silica gel column chromatography (elution solvent ether: hexane = 1: 5 to 1: 3 gradient elution) to obtain the desired 3-cyclopropyl-2- (2-pentyl-3-oxo-cyclopentyl). Acetyl-3-oxopropanenitrile (cis form) (3.08 g) was obtained.
n _D ²⁰ 1.5195.

Synthesis example 4

  To a solution of potassium t-butoxide (6.03 g) in THF (60 ml) was added dropwise a solution of ethyl cyanoacetate (2.85 g) in THF (20 ml) at 10 ° C., and the mixture was further stirred for 30 minutes. To this solution, a solution of (2-pentyl-3-oxo-cyclopentyl) acetic acid chloride (cis isomer) (5.64 g) in THF (20 ml) was added dropwise at 5 ° C., and the mixture was further stirred at room temperature for 3 hours. After the reaction, the solvent was distilled off under reduced pressure, a small amount of water was added to the residue, the aqueous layer was made weakly acidic with dilute hydrochloric acid, and extracted with ethyl acetate (100 ml). The organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The crude product was purified by silica gel column chromatography (ether: hexane = 1: 5) to obtain the desired ethyl 2-cyano-2- (2-pentyl-3-oxo-cyclopentyl) acetate (cis isomer) (5.21 g). )

n _D ²⁰ 1.4920.

  The compounds obtained in the same manner as in Synthesis Examples 1 to 4 are shown in Table 1 below together with the compounds synthesized in Synthesis Examples 1 to 4.

In Table 1,
Q-1 is the group

を示し、
Ｑ−２は基

Indicate
Q-2 is the group

を示し、
Ｑ−３は基

Indicate
Q-3 is the group

を示す。

Indicates.

  Me represents methyl, Et represents ethyl, OMe represents methoxy, and OEt represents ethoxy.

参考例１

Reference example 1

1,3-cyclohexanedione (1.12 g) and triethylamine (1.2
To a solution of 0 g) in THF (40 ml), a solution of (2-pentyl-3-oxo-cyclopentyl) acetyl chloride (cis form) (2.31 g) in THF (20 ml) was added dropwise at 0 ° C. After stirring at this temperature for 1 hour, the mixture was further stirred at room temperature for 5 hours. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure to obtain oily 1- (2-pentyl-3-oxo-cyclopentyl) acetoxy-cyclohexen-3-one (cis form) (3.13 g).
Used in the next reaction without purification.

Reference example 2

  To a solution of (2-pentyl-3-oxo-cyclopentyl) acetic acid methyl ester (cis isomer) (11.3 g) in ethanol (100 ml) at 0 ° C., 1.05 equivalent of an aqueous potassium hydroxide solution was added dropwise. Stir for 3 hours. After the reaction, the solvent was removed at room temperature under reduced pressure, and the residue was dissolved in water (40 ml). The aqueous solution was washed with a small amount of ether, neutralized with dilute hydrochloric acid under cooling, and extracted with ethyl acetate (100 ml). After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to obtain (2-pentyl-3-oxo-cyclopentyl) acetic acid (cis isomer) (10.56 g).

  Without purifying the carboxylic acid, oxalyl chloride (6.5 g) was added dropwise in ethyl acetate (60 ml) under cooling, and the mixture was further heated to reflux for 2 hours. After leaving to be cooled to room temperature, the solvent was distilled off under reduced pressure to obtain (2-pentyl-3-oxo-cyclopentyl) acetyl chloride (cis form) (9.8 g).

  This acid chloride was used in the next reaction without further isolation and purification.

Reference example 3

  In the same manner as in Reference Example 2, {2- (Z-2-penten-1-yl) -3-oxo-cyclopentyl} acetic acid methyl ester (trans form) (25.0 g) was converted from {2- (Z-2 -Penten-1-yl) -3-oxo-cyclopentyl} acetic acid (trans form) (23.3 g) was obtained.

  Furthermore, using this carboxylic acid (6.31 g) and oxalyl chloride (4.95 g), the corresponding {2- (Z-2-penten-1-yl) -3-oxo-cyclopentyl} acetyl chloride (trans isomer) ) (6.72 g).

<Biological test example>
Test compound glufosinate 18.5% solution The test compound is a commercial product.

Test Example 1 : Herbicidal effect on weeds Preparation of active compound preparation carrier: 5 parts by weight of dimethylformamide (DMF) Emulsifier: 1 part by weight of benzyloxypolyglycol ether 1 part by weight of active compound preparation And the above-mentioned amount of carrier and emulsifier were mixed to obtain an emulsion. Dilute the prescribed amount of the preparation with water.
Test method:
In a greenhouse, 120 cm ² pot surface layers filled with field soil were seeded with various seeds of Inobie, Enokorogusa, Inubuyu, and Giant Inodes. Ten days after sowing cover (weeds are in average second leaf stage), a predetermined dilution of each active compound preparation was uniformly sprayed on the plant foliage of each test pot. The degree of herbicidal effect was investigated 5 days after spraying. In addition, the evaluation of the herbicidal effect was performed assuming that complete withering was 100% and 0% was not.

  As a representative example, for example, the results for the compounds of Compound Nos. 1, 2, 3, 23, 25, 26, 27 and 34 are shown in Table 2.

Test Example 2 : Herbicide efficacy enhancement test method:
In the greenhouse, the surface layer of each 45 cm ² pot filled with field soil was seeded with various seeds of Inobie, Enokorogusa, Inubiyu, and Giant Inodade. 10 days after sowing cover (weeds are on average second leaf stage), the predetermined dilutions of each active compound preparation and each active compound mixture preparation prepared in the same manner as in Test Example 1 above are used as plant stems and leaves of each test pot. Sprayed uniformly. The degree of herbicidal effect was investigated one day after spraying. In addition, the evaluation of the herbicidal effect was performed assuming that complete withering was 100% and 0% was not.

  As a representative example, Table 3 shows the results when, for example, the compounds of Compound Nos. 2, 25 and 27 are used as the compound of the present invention and glufosinate or glyphosate is used as a known herbicide.

<Formulation example>
Formulation Example 1 (Granule)
Add water (25 parts) to a mixture of the present compound No. 2 (10 parts), bentonite (montmorillonite) (30 parts), talc (talc) (58 parts), lignin sulfonate (2 parts) It hatches and it is made into a granule by drying at 40-50 degreeC as a 10-40 mesh granule with an extrusion-type granulator.

Formulation Example 2 (Granule)
Clay mineral grains (95 parts) having a particle size distribution of 0.2 to 2 mm are placed in a rotary mixer, and under rotation, together with a liquid diluent, the present compound No. 1 (5 parts) is sprayed and moistened uniformly, and then dried at 40 to 50 ° C. to give granules.

Formulation Example 3 (Emulsion)
This invention compound No. 25 (25 parts), phenoxaprop (5 parts), xylene (55 parts), polyoxyethylene alkylphenyl ether (8 parts), calcium alkylbenzenesulfonate (7 parts) are mixed and stirred to obtain an emulsion.

Formulation Example 4 (wettable powder)
This invention compound No. 26 (15 parts), mixture of white carbon (hydrous amorphous silicon oxide fine powder) and powdered clay (1: 5) (80 parts), sodium alkylbenzenesulfonate (2 parts), sodium alkylnaphthalenesulfonate formalin polymer (3 parts) is mixed with powder to make a wettable powder. Formulation Example 5 (Hydrated Granule) Compound No. 2 (20 parts), sodium lignin sulfonate (30 parts), bentonite (15 parts), calcined diatomaceous earth powder (35 parts), add water, extrude and dry with a 0.3 mm screen, Use hydrated granules.

Formulation Example 5 (hydrated granules)
This invention compound No. 27 (20 parts), sodium lignin sulfonate (30 parts), bentonite (15 parts) and calcined diatomaceous earth powder (35 parts) were thoroughly mixed, added water, extruded on a 0.3 mm screen and dried. Use hydrated granules.
Formulation Example 6 (Liquid)
This invention compound No. 27 (10 parts), glufosinate (10 parts), polyoxyethylene alkyl ether (5 parts), propylene glycol (5 parts) and water (70 parts) are mixed to obtain a liquid agent.

  As is apparent from the above biological test examples, the jasmonic acid derivative of the present invention has excellent herbicidal activity, is useful as a herbicide, and exhibits an excellent herbicidal efficacy enhancing action, useful as a herbicidal efficacy enhancer. It is.

Claims (6)

formula

Where
R ¹ represents alkyl or alkenyl,
Q is group

Indicate
R ² , R ³ , R ⁶ and R ⁷ each independently represent hydrogen or alkyl, or R ² together with R ⁷ forms ethylene,
R ⁴ and R ⁵ each independently represent hydrogen or alkyl, or together with the carbon atoms to which they are attached, C═O;
R ⁸ represents alkyl or haloalkyl,
R ⁹ represents alkyl or haloalkyl,
X represents O or S, and R ¹⁰ represents alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkoxyalkyl or haloalkoxy,
Or a salt thereof. R ¹ represents C _1-6 alkyl or C _2-6 alkenyl,
Q is based

Indicate
R ² , R ³ , R ⁶ and R ⁷ each independently represent hydrogen or C _1-6 alkyl, or R ² together with R ⁷ forms ethylene,
R ⁴ and R ⁵ each independently represent hydrogen or C _1-6 alkyl, or together with the carbon atoms to which they are attached, C═O;
R ⁸ represents C _1-6 alkyl or C _1-6 haloalkyl,
R ⁹ represents C _1-6 alkyl or C _1-6 haloalkyl,
X represents O or S, and R ¹⁰ is C _1-6 alkyl, C _3-7 cycloalkyl, C _3-6 alkenyl, C _3-6 alkynyl, C _1-6 alkoxy, C _1-4 alkoxyC _{1 -4} an alkyl or _{C 1-6} haloalkoxy,
The compound of claim 1. R ¹ represents butyl, pentyl, hexyl or 2-pentenyl,
Q is based

Indicate
R ² , R ³ , R ⁶ and R ⁷ each independently represent hydrogen or methyl, or R ² together with R ⁷ forms ethylene,
R ⁴ and R ⁵ each independently represent hydrogen or methyl, or together with the carbon atoms to which they are attached, C═O;
R ⁸ represents methyl or ethyl,
R ⁹ represents methyl, ethyl or 2,2,2-trifluoroethyl,
X represents O or S, and R ¹⁰ is ethyl, cyclopropyl, allyl, 4-pentenyl, 5-hexenyl, propargyl, 5-hexynyl, ethoxy, 2-methoxyethyl, 2-ethoxyethyl, 2,2,2 -Represents trifluoroethyloxy or 2,2,3,3,3-pentafluoropropyloxy,
The compound of claim 1.   A herbicide comprising the compound according to any one of claims 1 to 3 as an active ingredient.   A herbicidal efficacy enhancer comprising the compound according to any one of claims 1 to 3 as an active ingredient. formula

Where
R ¹ represents alkyl or alkenyl,
R ² , R ³ , R ⁶ and R ⁷ each independently represent hydrogen or alkyl, or R ² together with R ⁷ forms ethylene,
R ⁴ and R ⁵ each independently represent hydrogen or alkyl, or R ⁴ and R ⁵ together with the carbon atoms to which they are attached represent C═O,
A compound represented by