JPH10324606A - Stabilized solid agrochemical formulation - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject stabilized formulation remarkably inhibited in the degradation of halosulfuron methyl during its storage by adding a specific dispersant to the halosulfuron methyl. SOLUTION: This stabilized solid agrochemical formulation contains 0.05-10 wt.% of N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3-chloro-4- methoxycarbonyl-1-methylpyrazole-5-sulfonamide and 0.5-10 wt.% of a water-soluble or dispersible polymer (e.g. sodium polyacrylate) comprising one or more kinds of monomers selected from unsaturated carboxylic acids and their derivatives (e.g. acrylic acid, methacrylic acid, maleic acid or their alkyl esters and alkali metal salts) as essential ingredients.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to N-[(4,6-
Dimethoxypyrimidin-2-yl) aminocarbonyl]
The present invention relates to a stabilized pesticidal solid preparation which suppresses decomposition of -3-chloro-4-methoxycarbonyl-1-methylpyrazole-5-sulfonamide (hereinafter, referred to as halosulfuron-methyl (common name)) and is stabilized.

[0002]

2. Description of the Related Art In recent years, it has been found that a sulfonylurea herbicidal active ingredient has high activity as an active ingredient of a herbicide in an extremely small amount.
Stable with little decomposition, but when formulated into conventional agricultural chemical solid formulations, such as powders, wettable powders, granules, etc., the decomposition of the active ingredient is significantly accelerated during storage of the formulation . Therefore, a technique for suppressing and stabilizing the decomposition is demanded.

Hitherto, as a method for suppressing and stabilizing decomposition of a sulfonylurea herbicidal active ingredient, a method described in, for example, JP-A-59-205305 is known. This method is a method of stabilizing the active ingredient by forming a complex with β-cyclodextrin, but has a disadvantage that the use of expensive β-cyclodextrin results in high cost.

[0004]

An object of the present invention is to provide a technique for further stabilizing halosulfuron-methyl, which is a sulfonylurea-based herbicidal active ingredient contained in a pesticidal solid preparation.

[0005]

The present invention provides an N-[(4,
6-dimethoxypyrimidin-2-yl) aminocarbonyl] -3-chloro-4-methoxycarbonyl-1-methylpyrazole-5-sulfonamide (generic name: halosulfuronmethyl) and a specific dispersant (this specific dispersion The agent is a water-soluble or water-dispersible polymer having one or more monomers selected from the group consisting of unsaturated carboxylic acids and derivatives thereof as essential components). Further, the present invention relates to the above pesticidal solid preparation, wherein the halosulfuron methyl is 0.05 to 10% by weight and the specific dispersant is 0.5 to 10% by weight.

[0006] That is, the present invention relates to a stabilized pesticidal solid preparation which contains a specific dispersant in the pesticidal solid preparation, thereby significantly suppressing the degradation of halosulfuron-methyl during storage and thereby stabilizing the pesticide solid preparation.

[0007]

BEST MODE FOR CARRYING OUT THE INVENTION In the present invention, examples of unsaturated carboxylic acids include unsaturated carboxylic acids such as acrylic acid and methacrylic acid, and dicarboxylic acids such as maleic acid. Alkyl ester of the acid (the alkyl group usually has 2 to 2 carbon atoms)
0) Examples of the above-mentioned acid salts include alkali metal salts (such as sodium), ammonium salts, organic amine salts (triethanolamine salts) and mixtures thereof.

The admixture may be a copolymer of a monomer selected from unsaturated carboxylic acids and derivatives thereof with other monomers, and the other monomers may be styrene, isobutylene, diisobutylene, Vinyl acetate and the like. The molecular weight of the polymer is usually from 1,000 to 200,000, preferably from 5,000 to 50,000.

Examples of the water-soluble or water-dispersible polymer include sodium polyacrylate [Toxanone GR-30 (Sanyo Chemical Industries, Ltd.)
(Manufactured by Sanyo Kasei Kogyo Co., Ltd., neutralization degree: 100%), etc.]; maleic acid (1) / styrene (0.8) / methacrylic acid C ₁₁ ,
C ₁₃ , C ₁₅ Ziegler alcohol ester (0.2) copolymer (Na) (degree of neutralization 100%), maleic acid (1)
Styrene (0.7) copolymers of acrylic acid lauryl ester (0. 3) (Na) (degree of neutralization of 100%), maleic acid (1) Styrene (0.75) methacrylate C _11, C ₁₃ , C ₁₅ Ziegler alcohol ester (0.
1) Copolymer (Na) of methyl methacrylate (0.25) (degree of neutralization 100%), maleic acid (1) styrene (0.6) methacrylic acid-2-ethylhexyl ester (0.15) ) ・ Methyl methacrylate (0.3)
A copolymer of (Na) (degree of neutralization of 100%), maleic acid (1) Styrene (0.75) methacrylate C _12, C
₁₃ Ziegler alcohol ester (0.1) / methyl methacrylate (0.25) copolymer (Na salt) (degree of neutralization 90%), maleic acid (1) / styrene (0.7
5) Methacrylic acid C _12, C ₁₃ Ziegler alcohol ester (0.1) Methyl methacrylate (0.25)
(Ammonium salt) (neutralization degree 100%), maleic acid (1), styrene (0.75), methacrylic acid C11,13,15 Ziegler alcohol ester (0.1%)
2) Copolymer of methyl methacrylate (0.2) (K
Salt) (degree of neutralization of 100%), maleic acid (1) Styrene (0.75) methacrylate C _11, C _13, C ₁₅ Ziegler alcohol esters (0.1) - methyl methacrylate (0.2) (Na) (degree of neutralization 95%), maleic acid (1) / styrene (0.9) / methyl methacrylate (0.1) copolymer (ammonium salt)
(Neutralization degree 100%) (Na), maleic acid (1) / styrene (1) copolymer (Na) (neutralization degree 100%), sodium lignin sulfonate (manufactured by Sanyo Kokusaku Pulp Co., Ltd.), etc. Is mentioned. [Numbers in parentheses are moles when maleic acid is 1 mole. ]

In the pesticidal solid preparation of the present invention, the content of halosulfuron-methyl and the specific dispersant is 0.05 to 10 parts by weight of halosulfuron-methyl based on 100 parts by weight of the pesticidal solid preparation of the present invention. The specific dispersant is desirably 0.5 to 10 parts by weight, preferably 2 to 7 parts by weight. The solid agricultural chemical preparation of the present invention may contain commonly used surfactants, other auxiliaries, coloring agents and the like.

Examples of the surfactant include alkyl sulfosuccinates (eg, dioctyl sulfosuccinate), condensed phosphates (eg, tripolyphosphate), formalin condensates of naphthalenesulfonic acid and salts thereof, and formalin of alkylnaphthalenesulfonic acid. Condensates and salts thereof (eg, formalin condensates of methylnaphthalenesulfonic acid and salts thereof, formalin condensates of butylnaphthalenesulfonic acid and salts thereof, formalin condensates of alkylbenzenesulfonic acid and salts thereof), ligninsulfonic acid salts, phenol derivatives Condensates, polycarboxylates (eg, polyacrylic acid or a copolymer of maleic acid and diisobutylene), alkylbenzenesulfonates (eg, dodecylbenzenesulfonate), alkylnaphthalene sulfones (Eg, dibutyl naphthalene sulfonate), alkyl ether sulfate (eg, lauryl ether sulfate, polyoxyalkylene aryl phenyl ether sulfate, polyoxyalkylene phenyl ether sulfate), polyoxyalkylene aryl phenyl ether phosphate ester salt, polyoxyalkylene phenyl ether phosphorus Acid ester salt, polyoxyalkylene aryl phenyl ether, polyoxyalkylene phenyl ether, polyoxyphenyl ether, polyoxyalkylene ether,
Sorbitan fatty acid ester, polyoxyalkylene sorbitan alkyl ester, polyoxyalkylene fatty amide, polyoxyalkylene fatty amine, polyoxyalkylene fatty acid ester, polyoxyalkylene alkylamine, polyoxy fatty acid amide, polyoxyethylene / polyoxypropylene block copolymer, poly These include acetylene-based surfactants such as oxyethylene alkyl etherified polyoxypropylene, polyoxyethylenated polyethylene, acetylene glycol acetylene alcohol and alkylene oxide adduct thereof, silicone-based surfactants, fluorine-based surfactants and the like. However, the present invention is not limited to this.

As the extender, bentonite, talc,
Clay, diatomaceous earth, amorphous silicon dioxide, calcium carbonate, magnesium carbonate and other mineral fines commonly used as carriers for pesticides, glucose, sugar,
Lactose and other sugars, carboxymethylcellulose and its salts, starch and its derivatives, crystalline cellulose, wood flour,
Organic substances such as benzoic acid and salts thereof, sodium sulfate, ammonium sulfate, potassium chloride, water-soluble inorganic salts such as diammonium hydrogen phosphate, urea, and derivatives thereof,
Examples thereof include magnesium sulfate. These extenders are properly used depending on the purpose.

As the solvent, fatty acid esters (eg, amyl laurate, amyl myristate, butyl palmitate, amyl palmitate, hexyl palmitate, butyl stearate, amyl stearate, hexyl stearate, butyl oleate, olein) Amyl acid or butyl linoleate), fatty acid diesters (eg, diethyl succinate, dipropyl succinate, dibutyl succinate, diamyl succinate, dioctyl succinate, diethyl glutamate, dibutyl glutamate, diamyl glutamate, dioctyl glutamate, dibutyl adipate) , Diamyl adipate), phosphates (tributyl phosphate, triamyl phosphate, trioctyl phosphate, butyl diphenyl phosphate,

Octyl diphenyl phosphate or tri (chloroethyl) phosphate, etc., alkylbenzenes (eg, diethylbenzene, diisopropylbenzene, triisopropylbenzene, t-butylbenzene, di (t-butyl) benzene, diamylbenzene, triamylbenzene, Tetraamylbenzene, t-amylbenzene, di (t-amyl) benzene, octylbenzene, dodecylbenzene, didodecylbenzene, etc., diphenylmethanes (for example, phenylxylylethane, phenylxylylpropane, trixylylethane, dixylmethane, Benzoic acid esters (eg, methyl benzoate, ethyl benzoate, butyl benzoate, amyl benzoate, tridecyl benzoate), phthalic acid esters (eg, If, dimethyl phthalate,
Diethyl phthalate, dibutyl phthalate, ditridecyl phthalate, etc.), vegetable oils (eg, rapeseed oil, soybean oil, olive oil, corn oil, coconut oil, castor oil, etc.), epoxidized vegetable oils (eg, epoxidized rapeseed oil, epoxidized soybean oil) Etc.).

Examples of the binder include starch, starch derivatives, water-soluble polymers such as polyethylene glycol, polyvinyl alcohol, polyvinylpyrrolidone, and carboxymethyl cellulose salt. Next, examples and test examples of the present invention will be specifically described. However, the present invention is not limited only to these Examples and Test Examples. All parts below are parts by weight.

Example 1 Granules 0.32 parts of finely pulverized halosulfuron-methyl, sodium polyacrylate (Toxanone GR-31A, Sanyo Chemical Industries, Ltd.)
5), dialkyl sulfosuccinate salt 1.
5 parts, bentonite 30 parts, calcium carbonate 64.68
Were uniformly mixed, and 20 parts of water was added to the mixture and kneaded. This kneaded material was granulated with a 1.2 mm screen using an extrusion granulator. This was dried at 50 ° C. for 2 hours to obtain the granules of the present invention.

Example 2 Granules 0.32 parts of finely pulverized halosulfuron-methyl and 7 parts of polyacrylate (Agrizole G-200, manufactured by Kao Corporation)
Parts, 1.5 parts of a dialkyl sulfosuccinate salt, 30 parts of bentonite, and 62.68 parts of calcium carbonate were uniformly mixed, and 20 parts of water was added to the mixture and kneaded. This kneaded material was granulated with a 1.2 mm screen using an extrusion granulator. This was dried at 50 ° C. for 2 hours to obtain the granules of the present invention.

Example 3 Granules 0.32 parts of finely pulverized halosulfuron methyl, sodium salt of polycarboxylic acid (Shalol AN-103P, Daiichi Kogyo Seiyaku Co., Ltd.)
5), dialkyl sulfosuccinate salt 1.
5 parts, bentonite 30 parts, calcium carbonate 64.68
Were uniformly mixed, and 20 parts of water was added to the mixture and kneaded. This kneaded material was granulated with a 1.2 mm screen using an extrusion granulator. This was dried at 50 ° C. for 2 hours to obtain the granules of the present invention.

Comparative Example 1 Granules A granule of Comparative Example 1 was obtained by performing the same treatment as in Example 1 except that the sodium polyacrylate was omitted. Next, an abuse test was carried out using each of the above-mentioned preparations, and the effect of stabilizing the pesticidal solid preparation of the present invention was examined.

Test Example 1 Abuse Test Each solid preparation obtained in Examples 1 to 3 and Comparative Example 1 was used as a sample in this test. Place the sample in a glass sample bottle with an inner stopper, place it in a 50 ° C
They were stored for 0 days and subjected to an abuse test. The content of the herbicidal active ingredient in the samples before and after the test was measured, and the rate of change over time (decomposition rate) was calculated. The results are shown in Table 1.

Rate of change with time (decomposition rate)% = (RS) / R × 100 R: content of active ingredient in sample before abuse test S: content of active ingredient in sample after abuse test The contents of the components were quantified by an internal standard method using liquid chromatography.

[0022]

[Table 1] Table 1 ────────────────────────────────── Sample dosage form Dispersant Degradation rate ( %) ────────────────────────────────── Example 2 Granules Polyacrylic acid Na salt 4.9 Example 3 Granules Polyacrylate 3.9 Example 4 Granules Polycarboxylate Na salt 5.8 ──────── Comparative Example 1 No granules 59.5 ──────────────────────────────── ──

As is clear from the results shown in Table 1, the degradation rate of the pesticidal solid preparation of the present invention to which polyacrylate and polycarboxylate were added was much higher than that of the non-added comparative example. It is suppressed and stabilized.

[0024]

The pesticidal solid preparation of the present invention to which a polyacrylate or polycarboxylate is added has a very low degradation rate and is stabilized.

Claims (2)

[Claims] (1) N-[(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -3-chloro-4-methoxycarbonyl-1-methylpyrazole-5-sulfonamide and a specific dispersant (this The specific dispersant is a water-soluble or water-dispersible polymer having one or more monomers selected from the group consisting of unsaturated carboxylic acids and derivatives thereof as essential components). A stabilized pesticide solid formulation. 2. N-[(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -3-chloro-4-methoxycarbonyl-1-methylpyrazole-5-sulfonamide is 0.05 to 10% by weight. The pesticidal solid preparation according to claim 1, wherein the specific dispersant is 0.5 to 10% by weight.