JPH0267209A - Herbicidal mixture - Google Patents

Abstract

PURPOSE:To obtain a herbicidal mixture, having a wide herbicidal spectrum and capable of exhibiting remarkable herbicidal effects in a small amount of chemical without exerting phytotoxicity on rice plant and sustaining the effect persistence for a long period by mixing a triazole-based compound with CG-148. CONSTITUTION:A herbicidal mixture obtained by mixing (A) a compound expressed by formula I [R1 and R2 are lower alkyl, cycloalkyl, alkenyl, alkynyl or, together with the N atom to which they are linked, form 4-6C azacycloalkane; A is formula II or V (X is H, lower alkyl, alkoxy, phenoxy, benzyl, etc.; m is 0-3); n is 0-2] with (B) CG-148 expressed by formula VI in an amount of 0.05-10pts.wt. based on 1pt.wt. ingredient (A).

Description

Detailed Description of the Invention The present invention represents a group represented by the general formula CI), where X is a hydrogen atom, a lower alkyl group optionally substituted with a hydroxyl group, a cycloalkyl group, an alkoxy group,
It represents an alkoxycarbonyl group, an alkylcarbonyl group, a phenoxy group, a benzyl group, an α-hydroxybenzyl group, a halogen, a nitro group, an ami7 group, or a trifluoromethyl group, where m is the number of 0.1.2 or 3, and n is 0.1
Or represents the number 2. ) (In the formula, R1 and R2 are the same or different and represent a lower alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, or R1 and R2 together with the nitrogen atom to which they are bonded have 4 to 4 carbon atoms. 6 represents azacycloalkane, A is the following formula: %Formula% represents a benzyl group, α-hydroxybenzyl group, halogen, nitro group, amino group or trifluoromethyl group, m represents 0.1.2 or -3'' (7) number,
And n represents the number 011 or 2. ) A triazole compound represented by the formula and CG represented by the formula
The present invention relates to a herbicidal composition prepared by mixing -148 and a herbicidal method characterized by using these compounds.

The compound represented by the general formula (I) is a compound described in the patent application No. Ef3-53153 which was invented by the present inventors and filed earlier, and the specification describes that the compound represented by the general formula (I) It is stated that the indicated compound exhibits an excellent herbicidal effect against Japanese millet and the like.

CG-148 is also known to be effective against perennial weeds such as broad-leaved weeds and Cyperaceae weeds. (Refer to Japanese Unexamined Patent Publication No. 57-58452) By the way, general formula (I)
The compound represented by has a weak herbicidal effect on well-grown broad-leaved weeds and weeds of the Cyperaceae family, and a high dose was required to exhibit sufficient efficacy.

On the other hand, CG-148, which is a sulfonylurea compound, is effective against broad-leaved weeds such as Japanese cypress and Japanese cypress at extremely low doses, but has little effect on Japanese millet (and shows phytotoxicity against rice when the dose is increased). There were other problems.

In recent years, Japanese millet, which is a harmful weed in rice fields, and broad-leaved weeds,
Frequent occurrence of perennial weeds such as Japanese cypress, bulrush, and weed has become a problem, and complete weed control cannot be expected by applying herbicides with a narrow herbicidal spectrum or in small amounts. For this reason, the same or different herbicides must be used several times or in large amounts, which not only requires labor and cost, but also causes many problems such as chemical damage to rice and persistence in soil. .

As a result of intensive research by the present inventors to solve the above-mentioned problems, we found that when the compound represented by the general formula CI) and CG-148 were mixed, surprisingly, the range of application that could be obtained by applying each as a single agent was found to be We have discovered completely unexpected synergistic effects, such as a wide herbicidal spectrum, a remarkable herbicidal effect at a low dose without causing any harm to rice, and long-lasting efficacy. This led to the present invention.

The compound represented by general formula (I), which is one of the active ingredients of the mixture of the present invention, is, for example, a compound represented by general formula (n) (wherein A and n represent the above-mentioned meanings). It can be obtained by reacting a compound of the following formula (1): (wherein YlRl and R2 have the above-mentioned meanings), and optionally oxidizing with a suitable oxidizing agent.

In the above reaction, the target compound is a sulfonyl compound (n = 1) or a sulfonyl compound (
n = 2), it is possible to use as starting material a compound of formula (I) in which the S moiety is similarly oxidized, or alternatively, to prepare first a compound of formula I in which S is unoxidized and optionally This may be oxidized.

The step of reacting oxidized or unoxidized compound (2) with compound (m) is performed in an amount of 1 equivalent or more, preferably 1 to 2, relative to compound (2).
1 to 2 equivalents, preferably 1 to 1.2 equivalents, of compound (1) are reacted in a suitable solvent in the presence of an equal amount of deoxidizing agent. The reaction temperature is suitably 0 to 100°C, preferably 20 to 70°C. Here, as a deoxidizing agent, an inorganic base such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate, or sodium hydride, an organic base such as triethylamine or pyridine, or as a solvent, a carbonized base such as benzene, toluene, or xylene. Hydrogen, halogenated hydrocarbons such as methylene chloride and chloroform, ethers such as diethyl ether, tetrahydrofuran, and dioxane, ketones such as acetone and methyl ethyl ketone, and other ethyl acetate esters, acetonitrile, dimethylformamide, pyridine, and dimethyl sulfoxide. , a solvent such as water, or a suitable mixed solvent thereof.

Further, the oxidation step can be performed, for example, by oxidizing with an oxidizing agent in a suitable solvent.

The oxidizing agents used here include hydrogen peroxide, potassium permanganate, inorganic oxidizing agents such as chromic acid, peracetic acid, m
Examples of the organic oxidizing agent include -chloroperbenzoic acid, and examples of the solvent used in this case include methylene chloride, chloroform, acetone, acetic acid, water, and a mixed solvent thereof. The reaction temperature is suitably 0 to 50°C, but depending on the type of solvent or the progress of the reaction, heating or cooling can be performed as appropriate.

Among the compounds represented by the general formula (I) thus obtained, the preferred embodiment for the mixture of the present invention and the compound represented by More preferred examples include compounds represented by formula (V), formula (V1), and formula (■).

In addition, CG-1, which is the other active ingredient of the mixture of the present invention
48 is, for example, the method QC described in the following publication.

The synergistic effect according to the present invention is observed in a wide range of mixing ratios, and C
G-148 is mixed in a proportion of 0.05 to 10 parts by weight,
Useful herbicides can be created. The thus obtained herbicide of the present invention can be highly effective when treated with soil before and after weed germination.

The mixture of the present invention may be sprayed as a raw material, but in order to make it more convenient to use, it can be mixed with various solid and liquid carriers used in the formulation of general agricultural chemicals to form wettable powders, emulsions, and oils. It can be manufactured into powders, granules, flowables, etc. Furthermore, auxiliary agents such as dispersants, diluents, emulsifiers, spreading agents, wetting agents, adsorbents, thickeners, antifoaming agents, and antifreezing agents may be added to the drug.

The carrier referred to herein may be either solid or liquid, or a combination thereof. Examples include talc, clay, bentonite, kaolin, diatomaceous earth, calcium carbonate, charcoal, starch, gum arabic, water, alcohol, kerosene, naphtha, xylene, cyclohexane,
Methylnaphthalene, benzene, acetone, dimethylphoλ
Examples include remamide, glycol ether, and N-methylpyrrolidone.

Examples of adjuvants include polyoxyethylene alkylphenyl ether, polyoxyethylene sorbitan monooleate, ethylene oxide propylene oxide copolymer, lignin sulfonate, sorbitan ester, soaps, sulfated oils, alkyl sulfate ester salts, petroleum Sulfonates, dioctyl sulfosuccinate salts, alkylbenzene sulfonic acids, aliphatic amine salts, quaternary ammonium salts, alkylpyridinium salts, alkyldimethylbetaine, alkylaminoethylglycine,
Polyglycol sulfate, alkylamine sulfonic acid, isopropyl phosphate, carboxymethyl cellulose, polyvinyl alcohol, hydroxypropyl cellulose, ethylene glycol, xanthan gum, etc. can be used.

In formulation, the mixing ratio of the mixture of the present invention can generally be freely selected within the range of 0.05% to 95% by weight, but preferably contains 1 to 70%. and the carrier is 70-99%, preferably 40-90%
, formulations containing 0 to 20%, preferably 1 to 7% of adjuvants are preferred.

In addition, a wider range of effects can be expected by mixing with other fungicides, herbicides, plant growth regulators, insecticides, acaricides, and other agricultural chemicals, fertilizers, and the like.

When actually using the mixture of the present invention, those skilled in the art will be able to appropriately select the amount to be used depending on the time of use, weather conditions, method of use, dosage form, place of use, target weeds, target crops, etc. As is clear from
Preferably it is 15 to 200 g per 10 ares.

Further, the herbicide of the present invention is usually used in the form of a mixture of the compound represented by the general formula (I) and CG-148, but after using one herbicide alone, the other herbicide is further applied. There is also an embodiment. Such methods are also included in the present invention.

Next, test examples will be given to specifically demonstrate the applicability of the present invention.

Test Example 1 A 115,000 are Wagner Posoto was filled with paddy soil (clay loam), water was added, and plowing was carried out to incubate Japanese millet, broad-leaved weeds (Azaena, Apsyllium, Kikashigusa, Chickweed).
We sowed seeds of Japanese cypress and Japanese firefly, and also planted tubers of Japanese cypress and Japanese cypress. Furthermore, rice at the two-leaf stage was treated with 2CI.
Three plants were planted at a depth of .

The chemical treatment was carried out by hand-sprinkling a predetermined amount of granules obtained in accordance with Formulation Example 1 described later on the water surface at the 7th pewter stage of sowing weeds and the 1-leaf stage of Japanese millet. Management and cultivation are carried out in a greenhouse.
Three weeks after the chemical treatment, the herbicidal effect and phytotoxicity of rice were investigated. The results are shown in Table 1.

In addition, the numerical values in the table indicate the herbicidal effect and the phytotoxicity to rice, and the specific values are as follows.

In addition, the numbers in parentheses in the table are the predicted weed suppression value (E) of the mixture calculated by the following formula of CO1by [:Co
1by1s, R,, WEEDS1 top 1.20-22.
1967 reference α, β: Weed suppression value when each component present in the mixture is applied as a single agent Table 1 As a result, the actual measured value of the weed suppression value of the mixture is In this case, it is larger than the expected value (E), proving that there is a synergistic effect.

Next, formulation examples of the herbicidal composition of the present invention will be shown.

Formulation Example 1 Compound (V) 1 part by weight CG-148
4 Sodium ligninsulfonate 2 Bentonite 30 Talc
63 These ingredients are mixed well until homogeneous and granulated to obtain granules.

Formulation Example 2 30 parts by weight CG-148 of the compound of the formula (■)
6 Sodium alkyl sulfate 2.5 Polyoxyethylene alkyl phenyl ether 2.5 Clay 59 These components are thoroughly mixed until uniform and pulverized to obtain a wettable powder.

Formulation Example 3 20 parts by weight of the compound CG-148
4 Alkylbenzene sulfonate 3 Polyoxyethylene alkylaryl ether 10 Quijirole 63 These components are thoroughly mixed until uniform and dissolved to obtain an emulsion.

Claims (1)

[Claims] 1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, R_1 and R_2 are the same or different,
Represents a lower alkyl group, cycloalkyl group, alkenyl group, alkynyl group, or R_1
and R_2 together with the nitrogen atom to which they are bonded represent an azacycloalkane having 4 to 6 carbon atoms, and A is the following formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
or ▲There are mathematical formulas, chemical formulas, tables, etc.▼ represents a group, where X is a hydrogen atom, a lower alkyl group which may be substituted with a hydroxyl group, a cycloalkyl group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyl group, Represents a phenoxy group, benzyl group, α-hydroxybenzyl group, halogen, nitro group, amino group or trifluoromethyl group, m is a number of 0, 1, 2 or 3, and n is a number of 0, 1 or 2. represent. ) A herbicide composition obtained by mixing a triazole compound represented by the formula ▲ ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ CG-148 represented by the formula ▼. 2) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, R_1 and R_2 are the same or different,
Represents a lower alkyl group, cycloalkyl group, alkenyl group, alkynyl group, or R_1
and R_2 together with the nitrogen atom to which they are bonded represent an azacycloalkane having 4 to 6 carbon atoms, and A is the following formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
or ▲There are mathematical formulas, chemical formulas, tables, etc.▼ represents a group, where X is a hydrogen atom, a lower alkyl group which may be substituted with a hydroxyl group, a cycloalkyl group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyl group, Represents a phenoxy group, benzyl group, α-hydroxybenzyl group, halogen, nitro group, amino group or trifluoromethyl group, m is a number of 0, 1, 2 or 3, and n is a number of 0, 1 or 2. represent. ) A weeding method characterized by using a triazole compound represented by the following and CG-148 represented by the formula ▲ Numerical formula, chemical formula, table, etc. ▼.