JPH07109206A - Stable agricultural chemical emulsion composition - Google Patents

Abstract

PURPOSE:To obtain a stable agricultural chemical emulsion composition capable of preventing deposition of crystals from an emulsion during storing at a low temperature and a spraying liquid diluted with water in using. CONSTITUTION:This stable agricultural chemical emulsion composition is obtained by dissolving a 3-substituted phenylpyrazole derivative of formula I [R is Y<1>R<3> (R<1> is alkyl, haloalkyl, alkenyl or alkynyl; Y<1> is O or S), formula II, formula III (R<4> is H or alkyl; R is H, alkyl, haloalkyl, alkenyl or alkynyl; Y<2> is O, S or NH), COOR<6> (R is alkyl, haloalkyl, alkenyl or alkynyl); R<1> is alkyl; R<2> is H, alkyl or haloalkyl; X and X are halogen; Y is O, S, SO or SO2] in a mixed solvent of a hydrocarbon-based nonpolar solvent (e.g. xylene, kerosine or methylnaphthalene) and a polar solvent (e.g. N-methyl-2-pyrrolidone or cyclohexanone) or a mixed solvent obtained by adding a low-polar solvent (e.g. N-octyl-2-pyrrolidone or N-dodecylcaprolactam) to the above mixed solvent.

Description

Detailed Description of the Invention

[0001]

This invention relates to at least one general formula
(I)

[Chemical 6] [In the formula, R is

Embedded image -Y ¹ R ³ (wherein, R ³ is a lower alkyl group, a lower haloalkyl group, a lower alkenyl group or a lower alkynyl group, Y ¹ is -O
-Or-S- is shown. ),

[0002]

Embedded image wherein —Y ² CH (R ⁴ ) C0—OR ⁵ (wherein R ⁴ represents a hydrogen atom or a lower alkyl group, R ⁵ represents a hydrogen atom, a lower alkyl group, a lower haloalkyl group, a lower alkenyl group or Is a lower alkynyl group, and Y ² is -O.
-, -S- or -NH- is shown. ),

Embedded image —COOCH (R ⁴ ) CO—Y ¹ R ⁵ (wherein R ⁴ , R ⁵ and Y ¹ are the same as above) or

[0003]

Embedded image wherein —COOR ⁶ (in the formula, R ⁶ represents a lower alkyl group, a lower haloalkyl group, a lower alkenyl group or a lower alkynyl group), R ¹ represents a lower alkyl group, and R ² represents a hydrogen atom. , A lower alkyl group or a lower haloalkyl group, X ¹ and X ² represent the same or different halogen atoms, and Y represents —O.
-, - S -, - SO- or -SO ₂ - shows a, n represents an integer of 0 to 1. In a pesticide emulsion composition comprising a 3-substituted pyrazole derivative represented by the formula (4) as an active ingredient, a mixed solvent of a hydrocarbon-based nonpolar solvent and a polar solvent or a mixed solvent obtained by adding a low polar solvent to the mixed solvent is used. Regarding a stable agricultural chemical emulsion composition characterized by being dissolved, it relates to an agricultural chemical emulsion composition improved for the purpose of preventing crystal precipitation from an emulsion during storage at low temperature and a spray solution diluted with water during use. is there.

[0004]

2. Description of the Related Art 3-Substituted phenylpyrazole derivatives represented by the general formula (I) are disclosed in JP-A-3-163063 and JP-A-3-163063.
The compound described in No. 211065 has excellent herbicidal activity against broad-leaved weeds that are harmful weeds in upland cultivation as a foliar-treating herbicide, and especially when applied in a wheat cultivation scene, Yaemgra, Hakobe, which is an important weed, It has a strong herbicidal effect on, but not limited to, Scutellaria baicalensis, dog chamomile, Astragalus chinensis, Spodoptera litura, Rhododendron japonicus, Scots burdock, Dutch minnow grass, white locust, dogwood, and willow.

[0005]

Conventionally, the herbicide for foliar treatment has been widely used in the form of emulsion, wettable powder, suspension, etc., and the emulsion has a high herbicidal effect. However, the 3-substituted phenylpyrazole derivative represented by the general formula (I) has poor solubility in an organic solvent, and it hardly dissolves in a hydrocarbon-based non-polar solvent generally used for emulsions. Is difficult. Various proposals have been made in order to obtain an emulsion of a compound having poor solubility in an organic solvent, for example: A method of dissolving an active ingredient in an alicyclic ketone (Japanese Patent Laid-Open No. 5069230/1975); A method of blending acetophenone and an aromatic solvent (Japanese Patent Publication No. 2-7282) is disclosed. However, although crystal precipitation during storage at low temperature is suppressed by this method, crystals precipitate in the spray liquid diluted with water during use in a short time and cause clogging of the spray nozzle. It is quite effective in suppressing the crystal precipitation in the above, but crystal precipitation is observed during low temperature storage, and the peculiar odor of acetophenone is strong, and there is concern about safety for users.

Further, as a method for preventing the precipitation of crystals in the diluted spray solution, a method in which an alkylcarboxylic acid dimethylamide is used as a solvent in an emulsion containing an azo compound as an active ingredient (JP-A-4-225901). ) Is disclosed, the alkylcarboxylic acid dimethylamides are highly toxic and have a problem in terms of user safety, and the general formula (I)
The solubility for the 3-substituted phenylpyrazole derivative represented by is also insufficient.

[0007]

DISCLOSURE OF THE INVENTION In an agricultural chemical emulsion composition containing at least one 3-substituted phenylpyrazole derivative represented by the general formula (I) as an active ingredient, a pesticidal emulsion composition is diluted in a preparation during low temperature storage and diluted with water. Although it is strongly desired to prevent the precipitation of crystals in the spray solution, an agricultural chemical emulsion composition that solves the above problems from the viewpoint of safety and physical properties has not been obtained.

[0008]

In view of the above situation, the inventors of the present invention have conducted extensive studies to solve the above-mentioned problems, and as a result, at least one 3-substituted phenylpyrazolone represented by the general formula (I) In an agricultural chemical emulsion composition containing a ru derivative as an active ingredient, the active ingredient is dissolved together with an emulsifier in a mixed solvent of a hydrocarbon-based nonpolar solvent and a polar solvent or a mixed solvent obtained by adding a low polar solvent to the mixed solvent. The inventors have completed the present invention by discovering that an agricultural chemical emulsion composition in which crystals do not precipitate can be obtained in the formulation during storage at low temperature and in the spray solution diluted with water.

A typical example of the 3-substituted phenylpyrazole derivative represented by the general formula (I) which is the active ingredient of the present invention is as follows.
Although illustrated in the table, the present invention is not limited thereto. General formula (I)

[Chemical 11]

[0010]

[Table 1]

[0011]

[Table 2]

[0012]

[Table 3]

[0013]

[Table 4]

The blending ratio of these active ingredients is rationally selected so as not to cause phytotoxicity to the crop to which it is applied and to exert a sufficient herbicidal effect on weeds other than the crop. To 100 parts by weight of the composition, 0.1 to 3 parts of the 3-substituted phenylpyrazole derivative represented by the general formula (I) is added.
It may be appropriately selected from the range of 10 parts by weight.

The hydrocarbon-based non-polar solvent used in the present invention is a hydrocarbon-based non-polar solvent generally used in pesticide emulsion compositions, such as xylene, kerosene, methylnaphthalene, Solvesso (Exxon Chemical Co., Ltd.). One or more kinds of solvents selected from such as solvents) can be exemplified. Examples of the polar solvent used in the present invention include N-methyl-2-pyrrolidone, cyclohexanone, N, N-dimethylformamide, and dimethylsulfoxide, and examples of the low polar solvent include N-octyl-2. -Pyrrolidone, N-dodecyl-2-pyrrolidone,
N-dodecyl caprolactam etc. can be illustrated. N-Methyl-2-pyrrolidone as a polar solvent and N-octyl-2-pyrrolidone as a low polarity solvent are both 2-pyrrolidone derivatives and have low toxicity to humans and animals, and to crops to which the pesticide emulsion composition of the present invention is applied. It is an organic solvent that does not cause chemical damage.

The mixing ratio of the hydrocarbon-based non-polar solvent, the polar solvent and the low-polarity solvent in the present invention is a mixed solvent of the hydrocarbon-based non-polar solvent and the polar solvent so that crystal precipitation does not occur in the preparation at -5 ° C. Mix a mixed solvent and a low-polarity solvent, and at least 2 in a spray solution diluted with water at the time of use.
It is necessary to prevent crystal precipitation for 4 hours, and the ratio is 50 to 85 parts by weight of the hydrocarbon-based nonpolar solvent and 2 to 25 parts by weight of the polar solvent with respect to 100 parts by weight of the pesticide emulsion composition.
The weight part and the low polar solvent may be appropriately selected and used from the range of 0 to 30 parts by weight, preferably the hydrocarbon non-polar solvent is 60 to 80 parts by weight, the polar solvent is 10 to 20 parts by weight and the low polarity. The solvent is in the range of 5 to 15 parts by weight.

To produce the pesticide emulsion composition of the present invention,
For example, a general formula that is at least one predetermined amount of active ingredient
A 3-substituted phenylpyrazole derivative represented by (I) can be mixed with a hydrocarbon-based non-polar solvent, a polar solvent, an emulsifier and, if necessary, a low polar solvent, and can be produced by a conventional method for pesticide formulation. . The type and amount of the emulsifier used in the present invention are not particularly limited, and examples thereof include polyoxyalkylene alkylphenyl ether, polyoxyalkylene allyl phenyl ether, polyoxyalkylene allyl phenyl ether formaldehyde condensation. Examples thereof include polyoxyalkylene castor oil ether, polyoxyalkylene alkyl ether phosphate, polyoxyalkylene allylphenyl ether phosphate, and alkylbenzene sulfonate, and these emulsifiers may be used alone or It can be mixed and used.

Further, if necessary, other organic solvent, stabilizer, dehydrating agent and other components may be added. Typical examples, comparative examples and test examples of the present invention are shown below, but the present invention is not limited to these. In the examples and comparative examples, “part” means “part by weight”.

[0019]

【Example】

Example 1 2.5 parts of compound 19, N-methyl-2-pyrrolidone 1
Part 0, Solvesso 200 (manufactured by Exxon Chemical Co., Ltd.) 7
7.5 parts and SP-3005X (manufactured by Toho Chemical Co., Ltd.) 1
An emulsion containing 2.5% of compound 19 was obtained by mixing and dissolving 0 part. Examples 2 to 5 In the same manner as in Example 1, pesticide emulsion compositions were obtained at the compounding ratios shown in Table 2.

[0020]

[Table 5]

[0021]

[Table 6]

Comparative Example 1 2.5 parts of compound 19, 87.5 parts of Solvesso 200 (manufactured by Exxon Chemical Co., Ltd.) and 10 parts of SP-3005X (manufactured by Toho Chemical Co., Ltd.) were mixed and dissolved to give compound 19. 2.5
% Containing emulsion was obtained. Comparative Example 2 2.5 parts of Compound 19, N-methyl-2-pyrrolidone 8
7.5 parts and SP-3005X10 parts were mixed and dissolved to obtain an emulsion containing 2.5% of compound 19.

Test Example 1 10 ml of each of the emulsions obtained in Examples and Comparative Examples was placed in a transparent bias bottle, sealed and stored at -5 ° C for 7 days, and the presence or absence of crystal precipitation was visually observed. A judgment was made. Criteria −: No crystal precipitation ±: Very slight crystal precipitation +: Small amount of crystal precipitation ++: Large amount of crystal precipitation +++: Very large amount of crystal precipitation Table 3 shows the results.

Test Example 2 100 ml graduated cylinder for emulsification test 3 times hard water 100
0.1 ml each of the emulsions obtained in Examples and Comparative Examples.
g was added to emulsify and allowed to stand at room temperature for 24 hours, and then visually observed for crystal precipitation, and the same criteria as in Example 1 were used. The results are shown in Table 3.

[0025]

[Table 7]

Claims (5)

[Claims] 1. At least one general formula (I): [In the formula, R represents -Y ¹ R ³ (In the formula, R ³ represents a lower alkyl group, a lower haloalkyl group, a lower alkenyl group or a lower alkynyl group, and Y ¹ represents -O).
-Or-S- is shown. ), —Y ² CH (R ⁴ ) C0-OR ⁵ (In the formula, R ⁴ represents a hydrogen atom or a lower alkyl group, and R ⁵ represents a hydrogen atom, a lower alkyl group, a lower haloalkyl group, a lower alkenyl. Group or a lower alkynyl group, Y ² is -O.
-, -S- or -NH- is shown. ), ## STR00004 ## -COOCH (R ⁴ ) CO-Y ¹ R ⁵ (in the formula, R ⁴ , R ⁵ and Y ¹ are the same as above) or ## STR00005 ## -COOR ⁶ (in the formula, R ⁶ Represents a lower alkyl group, a lower haloalkyl group, a lower alkenyl group or a lower alkynyl group), R ¹ represents a lower alkyl group, R ² represents a hydrogen atom, a lower alkyl group or a lower haloalkyl group, X ¹ And X ² represent the same or different halogen atoms, and Y represents —O.
-, - S -, - SO- or -SO ₂ - shows a, n represents an integer of 0 to 1. In a pesticide emulsion composition comprising a 3-substituted pyrazole derivative represented by the formula (4) as an active ingredient, a mixed solvent of a hydrocarbon-based nonpolar solvent and a polar solvent or a mixed solvent obtained by adding a low polar solvent to the mixed solvent is used. A stable agricultural chemical emulsion composition characterized by being dissolved. 2. The agricultural chemical emulsion composition according to claim 1, wherein the hydrocarbon-based non-polar solvent is one kind or two or more kinds selected from xylene, kerosene, methylnaphthalene and solvesso. 3. The pesticide emulsion composition according to claim 1, wherein the polar solvent is one or more selected from N-methyl-2-pyrrolidone, cyclohexanone, N, N-dimethylformamide or dimethylsulfoxide. . 4. The low-polarity solvent is one kind or two or more kinds selected from N-octyl-2-pyrrolidone, N-dodecyl-2-pyrrolidone or N-dodecylcaprolactam. Agrochemical emulsion composition. 5. A hydrocarbon-based nonpolar solvent in an amount of 50 to 85 parts by weight and a polar solvent in an amount of 5 to 100 parts by weight of the agricultural chemical emulsion composition.
25 parts by weight and 0-30 parts by weight of the low-polarity solvent are the agricultural chemical emulsion compositions according to any one of claims 1 to 4.