JPH11100303A - Improved agrochemical solid preparation - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an agrochemical solid preparation wherein a thifurzamide agrochemical solid preparation is prevented from deteriorating its physical properties with the lapse of time and from reducing the effectiveness of each agrochemical component. SOLUTION: This preparation is obtained by including one or more kinds of high boiling point liquids having each a boiling point of >=150 deg.C in an agrochemical solid preparation containing, as an agrochemical active ingredient, 2',6'-dibromo-2-'-methyl-4'-trifluoromethoxy-4-trifluoromethyl-1,3-thi azole-5- carboxyanilide (thifluzamide). Preferably, the high boiling point liquid is aromatic hydrocarbon, aliphatic hydrocarbon, alcohol, polyhydric alcohol, ether, ester, any amine, natural oil and fat, or lactone, more pref. any ester.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to an active ingredient represented by the following formula (I): 2 ', 6'-dibromo-2-methyl-4'- represented by
Trifluoromethoxy-4-trifluoromethyl-1,
The present invention relates to an agrochemical solid preparation in which deterioration of physical properties of a solid preparation containing 3-thiazole-5-carboxyanilide (general name: tifluzamide, hereinafter referred to as thifluzamide) is improved during long-term storage.

[0002]

2. Description of the Related Art Sheath blight is regarded as an important disease in rice cultivation, and thifluzamide is known to be a compound having a high activity against sheath blight (Japanese Patent Application Laid-Open No. 2-184680). The pesticide formulation containing the present compound can be directly sprayed or diluted and dispersed in water and then sprayed. Examples of the solid pesticide formulation include formulations such as powders, wettable powders, wettable powders, granules and tablets. Especially granules,
It is characterized by high fluidity, easy handling when spraying, and high safety for sprayers.

[0003]

However, in a solid preparation containing thifluzamide, during storage, crystals of the active ingredient precipitate on the surface of the solid preparation, and these adhere to each other's particles to cause agglomeration or decrease the fluidity. It became clear that the problem of worsening occurred. These phenomena not only cause troubles during use such as deterioration of spraying workability and clogging of the spraying machine, but also may cause partial lack of effects or chemical damage due to segregation of active ingredients. Furthermore, in the case of granules and wettable powders, the crystals on the surface of the granules come off during use and disperse as fine powder, which is a problem in terms of safety, such as inhalation by spraying workers and scattering into the environment. Has been a challenge.

[0004]

Means for Solving the Problems Accordingly, the present inventors have:
As a result of various studies on a method for improving the deterioration of physical properties over time of a solid preparation containing thifluzamide, (1) a pesticide solid preparation containing tifluzamide and one or more high-boiling liquids having a boiling point of 150 ° C. or higher. (2) The agricultural chemical solid preparation according to (1), wherein the high boiling point liquid is an ester. However, the present inventors have found that the present invention prevents deterioration of the physical properties of a solid agricultural chemical over time and does not cause a decrease in the efficacy of an active agricultural chemical ingredient, and thus completed the present invention.

[0005]

BEST MODE FOR CARRYING OUT THE INVENTION The high-boiling liquid used in the present invention is preferably one having low flammability and low volatility from the viewpoint of safety during production and use, and any liquid having a boiling point of 150 ° C. or higher. Although not particularly limited, a liquid having a boiling point of 200 ° C. or higher is more preferable. As the high boiling point liquid used in the present invention, aromatic hydrocarbons, aliphatic hydrocarbons, alcohols, polyhydric alcohols, ethers, esters, amines,
Examples include natural fats and oils and lactones. Esters are particularly preferred, and esters derived from aromatic carboxylic acid esters, aliphatic carboxylic acid esters, phosphite esters, phosphate esters and polyhydric alcohols of glycerin, alkylene glycol and polyalkylene glycol are more preferred. Aromatic carboxylic esters and polyethylene glycol fatty acid esters are most preferred. Hereinafter, more specific examples will be given, but the present invention is not limited thereto. Tetraethylene glycol, octanediol, glycerin, diethylene glycol, triethylene glycol, glycerin diglycidyl ether, ethylene glycol diglycidyl ether, triethylene glycol monomethyl ether, phenoxyethanol, triethanolamine, glycerin diacetate, glycerin triacetate, N-hydroxy-2-ethyl-2 -Pyrrolidone, dialkyl adipate, dialkyl phthalate, polyethylene glycol dilaurate, polyethylene glycol monolaurate,
Examples include polyethylene glycol monooleate, polyoxyethylene castor oil, polyoxyethylene sorbitan palmitic acid monoester, polyoxyethylene sorbitan coconut oil fatty acid ester, and polyoxyethylene polyoxypropylene glycol. Further, as the high boiling point liquid used in the present invention, a pesticidal active ingredient which is liquid at normal temperature can be used. Examples of pesticidal active ingredients that are liquid at room temperature include fenthion (common name), fenitrothion (common name), diclofenthion (common name), pirimiphosmethyl (common name), diazinon (common name), isoxathion (common name), oxy Deprophos (generic name), Marathon (generic name), Thiometone (generic name), Ethylthiometone (generic name), Prothiophos (generic name), Sulfophos (generic name), Profenofos (generic name), Pyraclofos (generic name), DDVP (Generic name), Clofenvinphos (generic name), Propaphos (generic name), Carbosurphan (generic name), Benfracarb (generic name), Aresulin (generic name), Permethrin (generic name), Cyhalothrin (generic name) ), Cyfluthrin (generic name), cycloprothrin (generic name), fenvalerate ( Generic name), flucythrinate (common name), fluvalinate (common name), propargite (common name), 1,3
Dichlorpropene (generic name), DCIP (generic name), etoprophos (generic name), phosthiazate (generic name), edifenphos (generic name), propiconazole (generic name), pefurazoate (generic name), pyrifenox ( Generic name), Zinocap (generic name), Benthiazole (generic name), Echromezol (generic name), Frathiocarb (generic name), Kazusafos (generic name), Silafluofen (generic name), Cyanophos (generic name), Fentate (generic name) Name), formotion (generic name), nared (generic name), isofenphos (generic name), ethion (generic name), chlorpicrin (generic name), and iprovenphos (generic name), and carbosulfan and benflacarb preferable.

[0006] One or more high-boiling liquids may be used. The amount of the high-boiling liquid is not particularly limited, but is preferably 0.05 to 30 parts, and more preferably 0.5 to 30 parts per part of thifluzamide. Use 20 parts. In the preparation of the present invention, thifluzamide does not need to be dissolved in a high boiling point liquid, and when completely dissolved and added, the effect of preventing crystallization may be rather reduced.

[0007] In the solid agricultural chemical preparation of the present invention, other auxiliaries used in ordinary agricultural chemical preparations can be used.
For example, surfactants such as anionic, nonionic, cationic and betaine surfactants can be mentioned, and among them, anionic, nonionic and mixed surfactants are desirable. These surfactants can be used alone or in combination of two or more. Further, solid carriers used in ordinary agricultural chemical formulations are also used. For example, mineral fine powders such as bentonite, calcium carbonate, clay, talc, and diatomaceous earth, vegetable fine powders such as wood powder, and polymer fine powders, and fertilizers can be used. These can also be used alone or in combination of two or more. In addition, an absorbent such as white carbon, a binder such as CMC-Na, a chelating agent such as sodium tripolyphosphate, various acids and bases, and various polymer compounds can be added.

[0008] In addition to thifluzamide, one or more pesticidal active ingredients such as other fungicides, insecticides and herbicides can be contained. Herbicides include, for example, pyrazosulfuron-ethyl (generic name), halosulfuron-methyl (generic name), bensulfuron-methyl (generic name), imazosulfuron (generic name), azimusulfuron (generic name), SWEP (generic name), ethoxy Sulfuron (generic name), cyclosulfamuron (generic name), esprocarb (generic name), mefenacet (generic name), cafenstrol (generic name), etobenzamide (generic name), cyhalofop butyl (generic name), Daimron (Generic name), piributicarb (generic name), benfresate (generic name),
Bentazone (generic name) and its salts, 2.4-D and its salts or esters, MCP and its salts or esters, molinate (generic name), benthiocarb (generic name), aminophos (generic name), pentoxazone (generic name) , Epoprodan (generic name), pyributicarb (generic name), tenichlor (generic name), pyrazolate (generic name), pyrazoxifene (generic name), benzofenap (generic name), dimethamethrin (generic name), bromobutide (generic name) , Butamiphos (generic name), dithiopyr (generic name), pyriminobac-methyl (generic name), symethylin (generic name) and anilofos (generic name). In pesticides,
For example, fipronil (generic name), imidacloprid (generic name), carbosulfan (generic name), benflacarp (generic name), cartap (generic name), buprofezin (generic name), etofenprox (generic name) and the like can be mentioned. Can be In fungicides, for example, tricyclazole (generic name), probenazole (generic name), azoxystrobin (generic name), furaside (generic name), flutranil (generic name), penciclone (generic name), pyroquilon (generic name) Name), diclosimet (generic name), flametopil (generic name), carpropamide (generic name), S-2900
(Test name), kresoxime methyl (generic name), methinophene (generic name), acetamidoprid (generic name), spinosad (generic name), chlorfenapyr (generic name), clothiazine (generic name) and CG-213 (test name) No.

The preparation of the present invention can be produced according to a usual production method of each dosage form, and is not particularly limited. Also,
The method for adding the high-boiling liquid is not particularly limited, and it may be mixed with thifluzamide and added simultaneously or separately.
For example, in the case of kneaded granules, thifluzamide pulverized as necessary, thifluzamide and other raw materials excluding the high boiling point liquid are mixed, a high boiling point liquid is added and mixed, an appropriate amount of water is added and kneaded, and then extruded. Molded by a method such as granulation,
A method of drying and sizing, or a method of mixing thifluzamide and a high boiling point liquid in advance, mixing with other raw materials, adding an appropriate amount of water, kneading, molding by extrusion granulation, drying, and sizing. , And thifluzamide, thifluzamide and other raw materials except for the high-boiling liquid are mixed, and a mixture of the high-boiling liquid and an appropriate amount of water is added in advance, kneaded, molded by extrusion granulation, and dried. And sizing method. Alternatively, granules containing thifluzamide which has been granulated in advance may be impregnated with a high boiling point liquid. In this case, if necessary, an adsorbent powder such as white carbon may be added.

[0010]

EXAMPLES Next, examples and test examples of the present invention will be specifically described. However, the present invention is not limited to only these examples and test examples. The following parts all represent parts by weight. [Examples 1 to 27] Table 1 shows the amount of thifluzamide added in each example, the added high-boiling liquid of the present invention, the amount added, and other components and preparation methods as formulation examples.

[Formulation Example 1] The amount of thifluzamide drug substance described in Table 1, sodium alkylbenzenesulfonate 0.5
Parts, sodium ligninsulfonate 5 parts, sodium tripolyphosphate 2 parts, bentonite 40 parts, high boiling point liquid The amount shown in Table 1 and the amount of calcium carbonate in which the total amount other than water becomes 100 parts is a universal mixer (made by Dalton) ) And a 40% aqueous solution of sodium polyacrylate 2.5
And 13 parts of water were added and kneaded. This is called a caliber of 0.
Granulation was performed using an extrusion-type granulator equipped with an 8 mm screen, and dried at 50 ° C. to obtain a granule of the present invention.

Formulation Example 2 Thifluzamide drug substance The amount shown in Table 1, sodium alkylbenzenesulfonate 0.5
Parts, sodium ligninsulfonate 5 parts, sodium tripolyphosphate 2 parts, 94137TX (Takemoto Oil & Fat Co., Ltd.) 4 parts, bentonite 40 parts, high boiling point liquid The amount shown in Table 1 and the total amount other than water become 100 parts. The amount of calcium carbonate was mixed with a universal mixer (manufactured by Dalton), and 2.5 parts of a 40% aqueous solution of sodium polyacrylate and 13 parts of water were mixed and kneaded. 0.8mm diameter
Granulation using an extrusion granulator equipped with a screen of
Drying at 50 ° C. yielded the granules of the present invention.

Formulation Example 3 Thifluzamide drug substance The amount shown in Table 1, sodium alkylbenzenesulfonate 0.5
Parts, sodium ligninsulfonate 5 parts, sodium tripolyphosphate 2 parts, solpol CA-42 (Toho Chemical Co., Ltd.) 1 part, bentonite 40 parts, high boiling point liquid Table 1 and the total amount other than water are 100 Parts of calcium carbonate were mixed with a universal mixer (manufactured by Dalton), and 2.5 parts of a 40% aqueous solution of sodium polyacrylate and 13 parts of water were mixed and kneaded. 0.8mm diameter
Granulation using an extrusion granulator equipped with a screen of
Drying at 50 ° C. yielded the granules of the present invention.

[Formulation Example 4] The amount of the thifluzamide drug substance as shown in Table 1, 5 parts of sodium ligninsulfonate, 2 parts of sodium tripolyphosphate, 40 parts of bentonite, the amount of the high boiling liquid shown in Table 1, and the total amount other than water Blender (made by Dalton) with 100 parts of calcium carbonate
And a 40% aqueous solution of sodium polyacrylate
2.5 parts and 13 parts of water were mixed and added and kneaded. This was granulated using an extrusion-type granulator equipped with a screen having a diameter of 0.8 mm, and dried at 50 ° C. to obtain a granule of the present invention.

[Formulation Example 5] The thifluzamide drug substance, the amount described in Table 1, CMC-Na 2 parts, hydrous calcium silicate
3 parts, 20 parts of bentonite and 70 parts of clay were mixed with a universal mixer (made by Dalton), and 21 parts of water was added thereto.
Kneaded. This kneaded material is granulated using an extrusion granulator equipped with a screen having a diameter of 1.0 mm, and dried at 50 ° C. to obtain granules containing thifluzamide. The granules were impregnated with the amount shown in Table 1 in a universal mixer (manufactured by Dalton) to obtain the granules of the present invention.

Comparative Examples 1-2 Table 2 shows the amount of thifluzamide added in each comparative example. Further, other components and production methods in the comparative examples are shown in the following comparative preparation examples. Table 2

[Comparative Formulation Example] The amount of the thifluzamide drug substance described in Table 2 and the amount of sodium alkylbenzenesulfonate 0.1.
5 parts, 5 parts of sodium ligninsulfonate, 2 parts of sodium tripolyphosphate, 40 parts of bentonite and 100 parts of calcium carbonate in a total amount other than water mixed with a universal mixer (made by Dalton), and mixed with sodium polyacrylate 2.5 parts of 40% aqueous solution and 13 parts of water are mixed and added,
Kneaded. This was granulated using an extrusion-type granulator equipped with a screen having a diameter of 0.8 mm, and dried at 50 ° C. to obtain a granule of the present invention.

Test Example 20 g of the granules produced in Examples and Comparative Examples were placed in an aluminum bag of 12 cm in length and width and sealed.
After standing in a 50 ° C constant temperature bath for 10 days, the precipitation of crystals and the fluidity were evaluated. Regarding crystal precipitation, the surface of the granules was observed with a microscope (magnification: 50 times) and evaluated according to the criteria shown in Table 3. In addition, the fluidity immediately after production was evaluated as-, and the fluidity was evaluated according to the criteria shown in Table 4.

[0019]

[0020]

The test results are shown in Table 5. Table 5 As is clear from this table, it can be seen that the present invention improves the precipitation of crystals on the surface of granules and deterioration of fluidity during long-term storage of the solid formulation of thifluzamide pesticide.

[0022]

According to the present invention, crystallization of thifluzamide pesticide solid formulation on the surface of the solid formulation during long-term storage and deterioration of fluidity are improved, and as a result, handling at the time of spraying is easy (fluidity is low). Excellent, no impairment in spraying workability, no obstruction during use such as clogging of spraying machine), sufficient efficacy of active ingredient (no reduction in efficacy due to segregation of active ingredient, etc.) and safety High (no harm due to segregation of active ingredients, no problems such as inhalation by spraying workers and scattering into the environment)
An excellent solid formulation of thifluzamide pesticide is obtained.

Continued on the front page (72) Inventor Hojin Hayakawa 722-1, Tsuboi-cho, Funabashi-shi, Chiba Nissan Chemical Industry Co., Ltd. Central Research Laboratory (72) Inventor Kazuhiro Yamagishi 1470 Shirooka, Shirooka-cho, Minami-Saitama-gun, Saitama Nissan Chemical Industries, Ltd. Within the Institute for Biological Sciences (72) Inventor Osamu Sakano 722-1, Tsuboi-cho, Funabashi-shi, Chiba Nissan Chemical Industry Co., Ltd. (72) Inventor Yoshinobu Nakao 722-1, Tsuboi-cho, Funabashi-shi, Chiba Nissan Chemical Industry Co., Ltd. In the laboratory (72) Inventor Masaki Baba 722-1, Tsuboi-cho, Funabashi-shi, Chiba Pref. Nissan Chemical Industry Co., Ltd.

Claims (3)

[Claims] (1) 2 ', 6'-dibromo-2-methyl-
An agrochemical solid preparation containing 4'-trifluoromethoxy-4-trifluoromethyl-1,3-thiazole-5-carboxyanilide and at least one high-boiling liquid having a boiling point of at least 150 ° C. 2. The pesticidal solid preparation according to claim 1, wherein the high boiling point liquid is an ester. 3. 2 ', 6'-dibromo-2-methyl-
In an agrochemical solid preparation containing 4'-trifluoromethoxy-4-trifluoromethyl-1,3-thiazole-5-carboxyanilide as an agrochemical active ingredient, at least one high boiling liquid having a boiling point of 150 ° C. or more is used. A method for preventing deterioration of physical properties of a solid pesticide formulation over time, characterized in that it is contained.