JPS60132902A - Herbicide - Google Patents

Abstract

PURPOSE:A herbicide that contains, as an active ingredient, an unsaturated aliphatic monocarboxylic acid and its functional salt, thus showing excellent herbicidal effect against a wide range of weeds from annual and prennial narrow- leaf weeds to broad-leaf weeds. CONSTITUTION:A novel herbicide that contains, as an active ingredient, at least one selected from unsaturated aliphatic monocarboxylic acids of the formula [X, Y are H, halogen; X is a bond binding adjacent carbon atoms or aliphatic hydrocarbon group; R<1>, R<2> are H, halogen, hydrocarbon; R<3> is H, halogen, cyano, nitro; R<4> is OH, OR<5> (R<5> is alkyl, NR<6>R<7> (R<6>, R<7> are H, alkyl)] or its functional salt such as 2,9-decadienecarboxylic acid. EFFECT:The compounds of the formula can be easily prepared and excellent in their safety.

Description

DETAILED DESCRIPTION OF THE INVENTION (a) Technical field The present invention relates to a novel herbicide. More specifically, the present invention relates to a novel herbicide containing at least one of specific unsaturated aliphatic monocarboxylic acids and functional salts thereof as an active ingredient.

(b) Prior art Some aliphatic carboxylic acids are known to exhibit various physiological activities, such as sorbic acid, which is a bactericide used to prevent spoilage of foods such as cheese (U.S. (see Japanese Patent No. 3139378) and that 3-tesic acid has cholesterol synthesis inhibitory activity (Biochemical Journal (Biochem.J.)).

147, pp. 531-539 (1975)). On the other hand, β-(N-phenyl-N- It has been disclosed that methyl)amino-α-cyanoacrylic acid ester exhibits herbicidal activity and has Hill reaction (photochemical oxygen generation reaction by free chloroplasts) inhibitory activity.

(c) Purpose and structure of the invention The present inventors focused on the physiological activity of carboxylic acids, and aimed to obtain a herbicide with excellent herbicidal activity.
As a result of extensive physiological and physicochemical research on various carboxylic acid derivatives, it was surprisingly found that α, β
Unsaturated aliphatic monocarboxylic acids having double bonds in the and ω positions and their functional salts exhibit excellent herbicidal effects against a wide range of weeds, including annual and perennial narrow-leaved and broad-leaved weeds. They discovered this and arrived at the present invention.

That is, the present invention is directed to the following formula (■) (wherein, X and Y are the same or different and represent a hydrogen atom or a halogen atom; 13 straight-chain or branched aliphatic hydrocarbon residue; R1 and R2 are the same or different and represent a hydrogen atom, a halogen atom, or a hydrocarbon group having 1 to 7 carbon atoms; R2 is a hydrogen atom, a halogen Atom, cyano group,
or represents a nitro group; R4 is a hydroxy group, OR5 (
However, R5 represents a lower alkyl group) or a group represented by (wherein R4 and R7 are the same or different and represent a hydrogen atom or a lower alkyl group). The purpose of the present invention is to provide a herbicide containing at least one kind selected from unsaturated aliphatic monocarboxylic acids shown in ) and their functional salts as an active ingredient.

The present invention will be explained in more detail below.

The unsaturated aliphatic monocarboxylic acids in the present invention are those represented by the above general formula (■), and are linear or branched aliphatic monocarboxylic acids having 5 to 1.8 carbon atoms in the main chain. Belongs to acids. When the number of carbon atoms in the main chain is 4 or less or 19 or more, the herbicidal activity is weak and the intended purpose of the present invention cannot be achieved.

2 in the general formula (■) is a simple accepting bond between carbon atoms on both sides, or an aliphatic hydrocarbon residue having a linear or branched main chain with 1 to 13 carbon atoms, that is, a corresponding It represents a divalent group obtained by removing one hydrogen atom from each end carbon atom of an aliphatic hydrocarbon. The main chain herein means a chain portion bonded between carbon atoms on both sides of Z in formula (■). As 2, the aliphatic hydrocarbon residue is preferable because it has higher herbicidal activity.

The aliphatic hydrocarbon residue used has a carbon number within a theoretically limited range, but those having a total carbon number of 1 to 25 are usually preferred because of their high herbicidal activity. Further, the aliphatic hydrocarbon residue is a saturated or unsaturated hydrocarbon residue having a double bond.

When the aliphatic hydrocarbon residue is linear, it preferably has 2 to 10 carbon atoms, particularly preferably 3 to 7 carbon atoms. In addition, when the aliphatic hydrocarbon residue has a branch, it has one or more branched chains having fewer carbon atoms than its main chain, and the branched chain has 1 to 7 carbon atoms. In particular, an alkyl group having 1 to 5 carbon atoms is preferable, and in this case, the number of carbon atoms in the main chain is preferably 2 to 10, particularly preferably 3 to 7.

In addition, one or more hydrogen atoms of the aliphatic hydrocarbon residue as Z may be substituted with a substituent other than the aliphatic hydrocarbon group or a halogen atom, and examples of the substituent include Cyano group, hydroxy group, amino group, alkoxy group having 1 to 6 carbon atoms, alkylthio group,
Aralkoxy group having 7 to 10 carbon atoms, 6 to 10 carbon atoms
phenoxy groups, aliphatic hydrocarbon groups having 3 to 10 carbon atoms, and aromatic hydrocarbon groups having 6 to 10 carbon atoms.

When the aliphatic hydrocarbon residue is substituted, a halogen atom, a cyano group, an alkoxy group, an alkylthio group, or an alicyclic hydrocarbon group, especially a halogen atom, having 3 to 3 carbon atoms.
6 substituted with an alicyclic hydrocarbon group is preferred.

2 in the formula (■) is a linear saturated aliphatic hydrocarbon residue having 2 to 10 carbon atoms among the aliphatic hydrocarbon residues explained above, i.e., ethylene, trimethylene, tetramethylene, pentamethine, hexamethylene,
Hebutamethylene, octamethine, nonamethylene and decamethylene are particularly preferred because they have higher herbicide activity.

X and Y in the formula (■) are the same or different and represent a hydrogen atom or a halogen atom.

R1 and R2 in formula (■) are the same or different and represent a hydrogen atom, a halogen atom, or a hydrocarbon group having 1 to 7 carbon atoms. Examples of the hydrocarbon group include aliphatic hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups, and alkyl groups and alkenyl groups having 1 to 3 carbon atoms are preferred. As such R1 and R2, hydrogen atoms and halogen atoms are particularly preferable.

R3 in formula (■) represents a hydrogen atom, a halogen atom, a cyano group, or a nitro group, and the herbicidal activity is particularly high in the case of a hydrogen atom, a halogen atom, and a cyano group.

Furthermore, R4 in formula (■) is a hydroxy group.

means a group represented by Here, R5 represents a lower alkyl group, and R6 and R7 are the same or different and represent a hydrogen atom or a lower alkyl group. Such lower alkyl groups preferably have 1 to 3 carbon atoms.

As R4 in the general formula (■) explained above, a hydroxy group is particularly preferable because of its high herbicidal activity.

The unsaturated aliphatic monocarboxylic acids of the present invention represented by the general formula (■) may be either the cis form or the trans form, or may be a mixture of both.

Furthermore, in the present invention, a so-called functional salt of the unsaturated aliphatic monocarboxylic acid represented by the general formula (■) that retains the herbicidal effect may be used. Examples of the functional salts include alkali metal salts, alkaline earth metal salts, ammonium salts, and salts with amines of the carboxylic acid.

Here, examples of the alkali metal salts include lithium salts, sodium salts, potassium salts, etc., and examples of the alkaline earth metal salts include calcium salts, magnesium salts, etc.

Further, R8 in the above formula is a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms. The hydrocarbon group having 1 to 20 carbon atoms refers to an aliphatic hydrocarbon group having 1 to 20 carbon atoms and an aromatic hydrocarbon group having 6 to 20 carbon atoms.

Preferred hydrocarbon groups for R7 and R8 include:
It is a saturated aliphatic or alicyclic hydrocarbon group having 1 to 15 carbon atoms, and a hydrogen atom is also preferred as R7.

Preferred functional salts of the carboxylic acid derivative represented by the general formula (■) in the present invention in terms of herbicidal activity are ammonium salts.

The method for producing the unsaturated aliphatic monocarboxylic acids of the present invention may be any commonly used method.

When using the herbicide of the present invention: Although the active ingredient, the unsaturated aliphatic monocarboxylic acid of the formula (■), may be treated itself, granules, wettable powders, powders, emulsions, It can also be processed and used in any formulation form such as fine granules, flowables, suspensions, etc. Herbicides in these formulations include talc, bentonite, clay, kaolin, diatomaceous earth, white carbon, vermiculite,
Solid carriers such as slaked lime, ammonium sulfate, and urea; Liquid carriers such as water, alcohol, dioxane, acetone, xylene, cyclohexane, methylnaphthalene, dimethylformamide, etc.; alkyl sulfate esters, alkyl sulfonic acids, lignin sulfonates, polyoxyethylene glyfur Ethers, polyoxyethylene alkylaryl ether,
Emulsifiers and dispersants such as polyoxyethylene sorbitan monoalkylate and dinaphthylmethane disulfonate; and one or more of various auxiliary agents such as carboxymethyl cellulose and gum arabic may be used together with the active ingredients as appropriate. It is manufactured by blending, mixing, dissolving, or granulating. The herbicide of the present invention produced in this manner and in the form of a preparation usually contains 0.0.1 to about 99% by weight, preferably about 0.1 to about 95% by weight of the unsaturated aliphatic compound. It is desirable to contain monocarboxylic acids as active ingredients.

When the unsaturated aliphatic monocarboxylic acids of the present invention or the herbicides in the form of formulations containing the unsaturated aliphatic monocarboxylic acids as active ingredients are used, for example, in liquid or wet particulate form, the formulation usually includes: One or more surfactants may be included in an amount sufficient to readily disperse the active ingredient in water or oil. Of course, the monthly salary of "surfactant" also includes wetting agents, dispersing agents, suspending agents, spreading agents, and emulsifying agents.

(d) Effect The herbicide containing unsaturated aliphatic monocarboxylic acids as an active ingredient in the present invention has both water solubility and oil solubility as described above, so it can be used for foliage treatment, soil treatment, etc. Although it exhibits excellent herbicidal effects by any treatment method, it is particularly characterized by extremely excellent herbicidal effects in foliar and foliage treatments.

Furthermore, the herbicide of the present invention exhibits strong herbicidal activity against not only annual weeds such as cylindrical herbaceous and hemlockweed, but also perennial weeds such as plantain and commonweed.

Further, the herbicide of the present invention has the advantage that its active ingredient is easy to produce and is excellent in terms of safety.

(e) Examples The present invention will be further explained below with reference to Examples, but the present invention is not limited by these Examples in any way.

Furthermore, in the examples, "parts" means "parts by weight."

Example 1 0.1 part of 2,9-decadienecarboxylic acid was added to a mixed solution of 12.5 parts of water and 12.5 parts of acetone, and 0.013 parts of 80RPOL 2680 (Toho Chemical System) was added as a spreading agent.
After spraying a mixture containing 30% of the total amount of 100% of the total amount on the leaves of previously cultivated Himedion, Physifolia, Plantain, and Red-winged sedge three times over a period of approximately 1.5 hours, the cultivation was continued and the degree of withering of each was observed with the naked eye. A withering experiment was conducted. After processing 3
The degree of withering after several days is listed in Table 1. The degree of withering, that is, the degree of withering is used as an indicator of the degree of withering.
The so-called 5-stage method was used to represent the state in which the whole plant is wilted and dead, and the state is divided into four equal parts to indicate the intermediate state.

Reference example 1 SORP to a mixed solution of 12.5 parts of water and 12.5 parts of acetone
A blight experiment similar to that in Example 1 was conducted using a mixed solution to which 0.013 part of OL 2680 was added. The results are shown in Table 1.

Claims (1)

[Claims] The following formula (■) (wherein, X and Y are the same or different and represent a hydrogen atom or a halogen atom; Z is a bond between carbon atoms on both sides,
Alternatively, it represents a linear or branched aliphatic hydrocarbon group having a main chain of 1 to 13 carbon atoms; R1 and R2 are the same or different and represent a hydrogen atom, a halogen atom, or a hydrocarbon group having 1 to 7 carbon atoms; R3 is a hydrogen atom, a halogen atom,
Represents a cyano group or a nitro group; R4 is a hydroxy group, a group represented by OR5 (wherein R5 represents a lower alkyl group), or (R4 and R7 are the same or different and represent a hydrogen atom or a lower alkyl group) represents a group represented by ) A herbicide containing at least 1m selected from unsaturated aliphatic monocarboxylic acids and functional salts thereof as an active ingredient.