JPH06312908A - Herbicidal composition - Google Patents

Abstract

PURPOSE:To obtain a herbicidal composition having high herbicidal activity of a benzoxazine-based compound against broad-leaved weeds and rapid activity development, also effective against moncotyledonous weeds. CONSTITUTION:A herbicidal composition comprises (A) a benzoxazin-3-one derivative of formula I [R<1> and R<2> are lower alkyl; R<3> and R<4> are H or lower alkyl (substituted halogen, lower alkoxy or lower alkoxycarbonyl) which may be substituted] and (B) at least one kind selected from fluazifop-butyl of formula II, quinofop-ethyl of formula IV and a compound of formula V (X is H or Cl; R<1> and R<2> are H or lower alkyl; R<3> is alkyl, alkenyl, replaceable aryl, replaceable aralkyl or R<2> and R<3> form 3-4C alkylene) such as 2-(4-(3-chloro-5- trifluoromethyl-2-pyridyloxy)phenoxy)propionic acid-2-oxapropyl ester as active ingredients.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a herbicidal composition.

[0002]

2. Description of the Related Art At present, many kinds of herbicides are used for weeding of agricultural land or non-agricultural land depending on the purpose and use. However, the types of weeds to be controlled are extremely large, and on the one hand, the development of more selective herbicides is required, while on the other hand, they have a broader herbicidal spectrum and are more potent. There is also a demand for the development of herbicides having a herbicidal effect.

In view of such circumstances, the present inventors have proposed a novel benzoxazine compound as a compound having excellent selectivity and high herbicidal activity (EPC Patent Publication No. 0479420A2 or Japanese Patent Laid-Open No. 5-279420). 497
(See Japanese Patent Publication No. 7). On the other hand, fluazifop-ethyl (A),
Quinofopethyl (B) and phenoxapropbutyl (C) are known phenoxypropionic acid-based herbicides, each of the following formula

[0004]

[Chemical 3]

It is a compound having a chemical structure represented by: As foliar treatment agents, these phenoxypropionic acid-based herbicides selectively act only on monocotyledon weeds and have no effect on broadleaf weeds.

[0006]

The benzoxazine compound is a compound showing a strong herbicidal activity against both broadleaf weeds and monocotyledonous weeds by foliar treatment or soil treatment. The effect is rather weak, and a relatively high dose is required to obtain a sufficient effect.
An object of the present invention is to develop a herbicide which is also effective for monocotyledon weeds, utilizing the characteristics of the benzoxazine-based compound that it exhibits high herbicidal activity and broad-spectrum activity against broadleaf weeds.

[0007]

Means for Solving the Problems As a result of intensive studies to solve the above problems, the present inventors have found that a specific compound among the benzoxazine compounds and a known phenoxypropionic acid herbicide By admixing at least one compound of adihopethyl, quinofopethyl, phenoxapropethyl, or an α-substituted ketone derivative described in JP-A-2-025466,
The present invention was completed by obtaining a composition having a fast-acting effect on monocotyledonous weeds and an excellent herbicidal effect. Here, Japanese Patent Laid-Open No.
The α-substituted ketone derivative described in JP-A-02-25466 is represented by the general formula (II):

[0008]

[Chemical 4] (In the formula, X is a hydrogen atom or a chlorine atom, R ¹ and R ² are each independently a hydrogen atom or a lower alkyl group, and R ³ is an alkyl group, an alkenyl group, an optionally substituted aryl group or may be substituted. Or a compound represented by an aralkyl group, or R ² and R ³ together represent an alkylene group having 3 or 4 carbon atoms. As an example of the α-substituted ketone derivative, 2- (4- (3) in which X is a chlorine atom, R ¹ and R ² are hydrogen atoms, and R ³ is a methyl group.
-Chloro-5-trifluoromethyl-2-pyridyloxy) phenoxy) propionic acid 2-oxopropyl ester (D) or 2- (4- (3-chloro-5-trifluoromethyl-2-pyridyloxy) phenoxy)
Propionic acid 2-oxobutyl ester, 2- (4-
(3-chloro-5-trifluoromethyl-2-pyridyloxy) phenoxy) propionic acid benzoylmethyl ester and the like can be mentioned.

That is, according to the present invention, (i) the general formula (I):

[0010]

[Chemical 5]

[Wherein R ¹ and R ² are lower alkyl groups, and R ³ and R ⁴ are the same or different and are a hydrogen atom or an optionally substituted lower alkyl group (wherein the substituent is a halogen atom, A lower alkoxy group or a lower alkoxycarbonyl group)], and (ii) fluazifopethyl and quinofop which are known phenoxypropionic acid herbicides. Ethyl, phenoxaprop ethyl, or α described in JP-A-2-025466.
-A herbicidal composition containing, as an active ingredient, at least one compound selected from the group of substituted ketone derivatives and the like.

In the above general formula (I), R ¹ , R ² ,
The lower alkyl group represented by R ³ and R ⁴ is a linear or branched alkyl group having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl. Group, isobutyl group and the like. Further, in the substituted lower alkyl group represented by R ³ and R ⁴ , the substituent that may be substituted is 1 to 3 of a fluorine atom, a chlorine atom or a bromine atom as a halogen atom, a methoxy group or an ethoxy group as a lower alkoxy group. Group, a lower alkoxy group having 1 to 4 carbon atoms such as a propoxy group or a butoxy group, a lower alkoxycarbonyl group such as a methoxycarbonyl group, an ethoxycarbonyl group or a propoxycarbonyl group having an alkoxy moiety having 1 to 6 carbon atoms,
Preferably, 1 to 4 lower alkoxycarbonyl groups can be mentioned.

The benzoxazin-3-one derivatives of general formula (I) are described in EPC Patent Publication No. 0479420A2.
It can be produced according to the method described in JP-A No. 5-4977. Representative examples of the compounds are shown in Table 1.

[0014]

[Table 1]

The known phenoxypropionic acid type herbicides fluazifopethyl (A), quinofop-ethyl (B) and phenoxaprop-ethyl (C) are commercially available drugs and can be easily obtained. it can. The α-substituted ketone derivative of the general formula (II) is disclosed in JP-A-2-02
It can be manufactured according to the method described in Japanese Patent No. 5466.

The herbicidal composition according to the present invention has an excellent herbicidal effect on both broadleaf weeds and monocot weeds by soil treatment or foliage treatment. The composition of the present invention may be used as it is, but various carriers, surfactants, other formulation auxiliary agents are mixed, and powders, granules, flowables, wettable powders, It is preferable to formulate and apply it in an emulsion, an oil agent or the like. Here, the carrier may be either solid or liquid, for example, talc,
Examples thereof include clay, bentonite, kaolin, diatomaceous earth, calcium carbonate, charcoal, starch, gum arabic, water, alcohol, kerosene, naphtha, xylene, cyclohexane, acetone and dimethylformamide. Examples of the surfactant include alkylsulfuric acid, alkylaryl sulfonates, dialkylsulfosuccinate salts and the like, and examples of other formulation auxiliaries include alginate, polyvinyl alcohol, CMC and the like.

The herbicidal composition according to the present invention can be provided in the form of emulsions, wettable powders, powders, granules and the like, and if necessary, various herbicides, various insecticides, fungicides, plants. You may mix and apply it to a growth regulator etc.

In carrying out the present invention, the concentration range of the components (i) and (ii) in the herbicidal composition of the present invention can be varied over a wide range, but generally, 1 to 50 g of the component (i) per 10 are. And components (ii) 1 to 100
It is preferably used in the range of g. When manufacturing the above-mentioned various preparations, it can be manufactured so as to contain the active ingredient in the range of 2 to 70%.

[0019]

The present invention will be described in more detail below with reference to formulation examples and test examples, but the present invention is not limited to these formulation examples and test examples. % In the examples is% by weight
It is.

Formulation Example-1 (Emulsion) Compound No. 3 5%, fluazifop-butyl 25
%, 20% polyoxyethylene alkyl ether and 50% xylene were uniformly mixed to obtain an emulsion.

Next, the effects of the composition of the present invention will be specifically shown by test examples. Test Example-1 (Stem and Leaf Treatment) A predetermined amount of a test compound (single agent or mixed agent) prepared as an emulsion according to Formulation Example-1 was applied to weeds naturally occurring in an outdoor field of 1 m × 1 m sandy loam soil. It was diluted with 200 liters of water per 10 ares, and sprayed uniformly over the entire surface of the foliage.
The effect was observed with the naked eye after 3 weeks from the treatment with the drug, and the degree of weeding (5:
Evaluation was made based on complete death to 0: no effect). The results obtained are shown in Table 2.

[0022]

[Table 2]

[0023]

INDUSTRIAL APPLICABILITY As described above, the herbicidal composition of the present invention has a synergistic effect of both agents and is capable of obtaining an excellent herbicidal effect with a low dose against a wide range of weeds which are difficult to control by a single agent. .

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[Procedure amendment]

[Submission date] March 16, 1994

[Procedure Amendment 1]

[Document name to be amended] Statement

[Name of item to be amended] Claims

[Correction method] Change

[Correction content]

[Claims]

[In the formula, R ¹ and R ² represent a lower alkyl group;
³ and R ⁴ are the same or different and each represents a hydrogen atom or an optionally substituted lower alkyl group (wherein the substituent is a halogen atom, a lower alkoxy group or a lower alkoxycarbonyl group)] And a benzoxazin-3-one derivative (ii) fluazifop- butyl , quinopop-ethyl, phenoxaprop-ethyl or the general formula (II):

Embedded image (wherein, X is a hydrogen atom or a chlorine atom, R ¹ and R ² are each independently a hydrogen atom or a lower alkyl group, R ³ is an alkyl group, an alkenyl group, an optionally substituted aryl group or a substituent) Or at least one compound selected from the group represented by R ² and R ³ together represents an alkylene group having 3 or 4 carbon atoms) as an active ingredient. A herbicidal composition.

[Procedure Amendment 2]

[Document name to be amended] Statement

[Name of item to be corrected] 0003

[Correction method] Change

[Correction content]

In view of such circumstances, the present inventors have proposed a novel benzoxazine compound as a compound having excellent selectivity and high herbicidal activity (EPC Patent Publication No. 0479420A2 or Japanese Patent Laid-Open No. 5-279420). 497
(See Japanese Patent Publication No. 7). On the other hand, fluazifop- butyl (A),
Quinofop ethyl (B) and fenoxaprop
Le (C) are produced in a known phenoxypropionic acid herbicides, the following formulas

[Procedure 3]

[Document name to be amended] Statement

[Correction target item name] 0007

[Correction method] Change

[Correction content]

[0007]

Means for Solving the Problems As a result of intensive studies to solve the above problems, the present inventors have found that a specific compound among the benzoxazine compounds and fluazifop which is a known phenoxypropionic acid herbicide. By mixing at least one compound of butyl , quinofop ethyl, phenoxaprop ethyl, or the α-substituted ketone derivative described in JP-A-2-025466,
The present invention was completed by obtaining a composition having a fast-acting effect on monocotyledonous weeds and an excellent herbicidal effect. Here, Japanese Patent Laid-Open No.
The α-substituted ketone derivative described in JP-A-02-25466 is represented by the general formula (II):

[Procedure amendment 4]

[Document name to be amended] Statement

[Correction target item name] 0011

[Correction method] Change

[Correction content]

[Wherein R ¹ and R ² are lower alkyl groups, and R ³ and R ⁴ are the same or different and are a hydrogen atom or an optionally substituted lower alkyl group (wherein the substituent is a halogen atom, A lower alkoxy group or a lower alkoxycarbonyl group)], and (ii) fluazifop- butyl , quinofop-ethyl, which is a known phenoxypropionic acid-based herbicide. Phenoxaprop ethyl, or α described in JP-A No. 2-025466.
-A herbicidal composition containing, as an active ingredient, at least one compound selected from the group of substituted ketone derivatives and the like.

[Procedure Amendment 5]

[Document name to be amended] Statement

[Name of item to be corrected] 0015

[Correction method] Change

[Correction content]

The known phenoxypropionic acid type herbicides fluazifop- butyl (A), quinofop-ethyl (B) and phenoxaprop-ethyl (C) are commercially available drugs and can be easily obtained. The α-substituted ketone derivative of the general formula (II) is disclosed in JP-A-2-02
It can be manufactured according to the method described in Japanese Patent No. 5466.

Claims (1)

[Claims] 1. (i) General formula (I): [Wherein R ¹ and R ² are lower alkyl groups, R ³ and R 2
⁴ is the same or different and represents a hydrogen atom or an optionally substituted lower alkyl group (wherein the substituent is either a halogen atom, a lower alkoxy group or a lower alkoxycarbonyl group). An oxazin-3-one derivative and (ii) fluazifop-ethyl, quino-fop-ethyl, phenoxaprop-ethyl or general formula (II): (In the formula, X is a hydrogen atom or a chlorine atom, R ¹ and R ² are each independently a hydrogen atom or a lower alkyl group, and R ³ is an alkyl group, an alkenyl group, an optionally substituted aryl group or may be substituted. A herbicidal composition containing, as an active ingredient, at least one compound selected from the group consisting of an aralkyl group or R ² and R ³ together representing an alkylene group having 3 or 4 carbon atoms. .