JPH08283108A - Herbicidal solid formulation - Google Patents

Abstract

PURPOSE: To obtain a stable herbicidal solid formulation capable of preventing the decomposition of a sulfonylurea compound by adding basic white carbon to a herbicide mixture comprising the sulfonylurea herbicidal compound and one or more kinds of other specific herbicidal compounds. CONSTITUTION: This herbicidal solid formulation is prepared by adding basic white carbon to a herbicide mixture comprising a sulfonylurea herbicidal compound and one or more kinds of other herbicidal compounds excluding dinitroaniline herbicides. The basic white carbon is preferably added in an amount of 2-40wt.% based on the solid formulation. The sulfonylurea herbicidal compound is preferably N-[(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl]-4- ethoxycarbonyl-1-methylpyrazole-5-sulfonamide, etc. The basic white carbon preferably has a hydrogen ion index of >=8, when dispersed in pure water to form a dispersion of 10wt.%.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a solid herbicidal preparation in which basic white carbon is used to prevent and stabilize the decomposition of sulfonylurea herbicidally active compounds.

[0002]

2. Description of the Related Art Recently, a sulfonylurea herbicidal active ingredient has been found to have high activity as an active ingredient of a herbicide in an extremely small amount, and the active ingredient itself is
Although it hardly decomposes and is stable, when it is formulated into a usual pesticide solid formulation, for example, powder, wettable powder, granule, etc., decomposition of the active ingredient is remarkably promoted during storage of the formulation, Therefore, there is a demand for a technique for suppressing and stabilizing the decomposition. As a technique for preventing this decomposition, a method of adding vegetable oil or the like to the preparation is known (JP-A-63-02).
3806).

[0003]

However, in the case of a sulfonylurea herbicidally active compound or a mixture with another herbicidally active compound, the sulfonylurea herbicidally active compound of Disassembly could not be prevented and its solution was desired.

[0004]

The present invention provides a mixed preparation comprising a sulfonylurea herbicidally active compound and one or more other herbicidal active compounds (dinitroaniline herbicidally active compounds), and a basic white carbon The present invention relates to a herbicide composition having good stability which prevents decomposition of a sulfonylurea herbicidally active compound during storage. In particular, the present invention relates to a solid herbicidal preparation containing a basic white carbon having a hydrogen ion index of 8 or more when the dispersion liquid is 10% by weight of pure water. The herbicidal composition of the present invention may contain a diluent, a surfactant and the like, if necessary.

The sulfonylurea herbicidal active ingredient is not particularly limited, but is, for example, the following formula: Q-SO ₂ NHCONH-R (wherein Q is a phenyl group which may be substituted with various substituents). , A benzyl group or a heterocyclic group, and R represents a pyrimidyl group or a triazyl group which may be substituted with various substituents).
Specific examples include the following compounds. However,
It is not limited to these compounds only.

(1) N-[(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -4-ethoxycarbonyl-1-methylpyrazole-5-sulfonamide (hereinafter abbreviated as compound A), (2 ) N-[(4,6-
Dimethoxypyrimidin-2-yl) aminocarbonyl]
-3-Chloro-4-methoxycarbonyl-1-methylpyrazole-5-sulfonamide (hereinafter abbreviated as compound B), (3) 2-chloro-N- (4-methoxy-6-
Methyl-1,3,5-triazin-2-yl-aminocarbonyl) benzenesulfonamide, (4) methyl = 2
-[3- (4-Methoxy-6-methyl-1,3,5-triazin-2-yl) ureidosulfonyl] benzoate, (5) methyl = 2- [3- (4,6-dimethylpyrimidine-2- Ile) ureidosulfonyl] benzoate,

(6) Methyl = 2- [3- (4,6-dimethoxypyrimidin-2-yl) ureidosulfonylmethyl] benzoate, (7) Ethyl = 2- [3- (4-chloro-6-methoxypyrimidine) -2-yl) ureidosulfonyl] benzoate, (8) 1- (4,6-dimethoxypyrimidin-2-yl) -3- (3-ethylsulfonyl-2-pyridylsulfonyl) urea, (9) 3-
(6-methoxy-4-methyl-1,3,5-triazin-2-yl) -1- [2- (2-chloroethoxy) phenylsulfonyl] urea, (10) methyl = 2- [3-
(4-methoxy-6-methyl-1,3,5-triazin-2-yl) -3-methylureidosulfonyl] benzoate,

(11) Methyl = 3- [3- (4-methoxy-6-methyl-1,3,5-triazin-2-yl)
Ureidosulfonyl] thiophenyl-2-carboxylate, (12) 1- (4,6-dimethoxypyrimidine-
2-yl) -3- (3-trifluoromethyl-2-pyridylsulfonyl) urea, (13) 2- (4,6-dimethoxypyrimidin-2-yl-carbosulfamoyl)
-N, N-dimethylnicotinamide, (14) 3-
(4,6-dimethoxy-1,3,5-triazine-2-
Yl) -1- [2- (2-methoxyethoxy) -phenylsulfonyl] urea, (15) 2- [3- (4,6-)
Bis (difluoromethoxy) -pyrimidin-2-yl)
Ureidosulfonyl] -benzoic acid methyl ester,

(16) Methyl = 2-[(4-ethoxy-
6-methylamino-1,3,5-triazin-2-yl) carbamoylsulfamoyl] benzoate, (1
7) N- (2-chloroimidazole [1,2-a] pyridin-3-yl-sulfonyl) -N '-(4,6-dimethoxy-2-pyrimidyl) urea, (18) N-
[(4,6-Dimethoxypyrimidin-2-yl) aminocarbonyl-1-methyl-4- (2-methyl-2H-tetrazol-5-yl) Other herbicidal active ingredients include the following compounds. To be However, the compounds are not limited to these compounds.

(1) 2- (α-naphthoxy) -N, N-
Diethylpropionamide (generic name: napropamide, hereinafter abbreviated as compound C), (2) methyl 5- (2,4-dichlorophenoxy) -2-nitrobenzoate (generic name:
Biphenox), (3) 4- (2,4-dichlorobenzoyl) -1,3-dimethyl-5-pyrazolyl-p-toluenesulfonate (general: pyrazolate), (4)
2- [4- (2,4-dichlorobenzoyl) -1,3-
Dimethylpyrazol-5-yloxy] acetophenone (generic name: pyrazoxifene), (5) 2- [4-
(2,4-dichloro-m-toluoyl) -1,3-dimethylpyrazol-5-yloxy] -4-methylacetophenone (generic name: benzophenap),

(6) 1- (α, α-dimethylbenzyl)
-3- (paratolyl) urea (generic name: Daimlon),
(7) (RS) -2-Bromo-N- (α, α-dimethylbenzyl) -3,3-dimethylbutyramide (generic name:
Bromobutide), (8) α- (2-naphthoxy) propionanilide (generic name: naproanilide), (9) (R
S) -2- (2,4-dichloro-m-tolyloxy) propionanilide (generic name: clomeprop), (1
0) 2,4-dichlorophenyl-3'-methoxy-4 '
-Nitrophenyl ether (generic name: clomethoxynil),

(11) 5-t-butyl-3- (2,4-
Dichloro-5-isopropoxyphenyl) -1,3,4
-Oxadiazolin-2-one (generic name: oxadiazon), (12) 2-benzothiazol-2-yloxy-N-methylacetanilide (generic name: mefenacet), (13) 2-chloro-2 ', 6'. -Diethyl-N
-(Butoxymethyl) acetanilide (generic name: butachlor), (14) S, S'-dimethyl = 2-difluoromethyl-4-isobutyl-6-trifluoromethylpyridine-3,5-dicarbothioate (generic name) : Dithiopyr), (15) (Z) -N-but-2-enyloxymethyl-2-chloro-2 ', 6'-diethylacetanilide (generic name: butenachlor),

(16) 2-chloro-2 ', 6'-diethyl-N- (2-propoxyethyl) acetanilide (generic name: pretilachlor), (17) 2,3-dihydro-3,3-dimethylbenzofuran- 5-yl-ethanesulfonate (generic name: benfrusate), (18) O-
3-t-butylphenyl = 6-methoxy-2-pyridyl (methyl) thiocarbamate (generic name: pyributycarb), (19) S- (4-chlorobenzyl) -N, N-
Diethyl thiocarbamate (generic name: ventiocarb), (20) S-1-methyl-1-phenylethyl =
Pyridine-1-carbothiate (generic name: dimepiperate),

(21) S-benzyl = 1,2-dimethylpropyl (ethyl) thiocarbamate (generic name: esprocerb), (22) S-ethylhexahydro-1H-
Azepine-1-carbothioate (generic name: molinate), (23) O-ethyl-o- (3-methyl-6-nitrophenyl) sec-butyl phosphoroamidothioate (generic name: butamiphos), (24) ) (1RS, 2S
R, 4SR) -1,4-epoxy-p-mens-2-yl-2-methylbenzyl ether (generic name: cinmethrin), (25) 2-methylthio-4,6-bis (ethylamino) -S -Triazine (generic name: cimetrin),

(26) O, O-diisopropyl-2-
(Benzenesulfonamido) ethyldithiophosphate (generic name: SAP), (27) 2-methylthio-4-ethylamino-6- (1,2-dimethylpropylamino)
-S-triazine (generic name: dimetamethrin), (2
8) 2-methylthio-4,6-bis (isopropylamino) -S-triazine (generic name: promethrin), (2
9) 2-amino-3-chloro-1,4-naphthoquinone (generic name: ACN), (30) 2-methyl-4-chlorophenoxybutyric acid (generic name: MCPB),

(31) 2-Methyl-4-chlorophenoxyacetic acid (generic name: MCP), (32) 5-dipropylamino-α, α, α-trifluoro-4,6-dinitro-
o-toluidine (generic name: prodiamine), (33)
2 ', 3'-dichloro-4-ethoxymethoxybenzanilide, (34) 1- (2-chlorobenzyl) -3-
(Α, α-Dimethylbenzyl) urea, (35) N-
[2 '-(3'-methoxy) -thienylmethyl] -N-
Chloroaceto-2,6-dimethylanilide,

(36) n-Butyl- (R) -2- [4-
(2-Fluoro-4-cyanophenoxy) phenoxy]
Propionate, (37) 3-N- (2-fluoro-4)
-Chloro-5-cyclopentyloxyphenyl) -5-
Isopropylidene-1,3-oxazolidine-2,4-
Dione, (38) 3,5-dichloro-N- (1,1-dimethylpropynyl) benzamide (generic name: curve)

White carbon is a general term for synthesized ultrafine powder of silicic acid anhydride, hydrous silicic acid, and hydrous calcium silicate, and when added to synthetic rubber and natural rubber like carbon black, shows a reinforcing effect on rubber. It is called white carbon because it is white. White carbon has a high oil absorption ability, and by utilizing this property, it is often used as a means for absorbing a liquid pesticide raw material at room temperature to powder it into a solid formulation such as powder, wettable powder and granules.
Some white carbons have different properties depending on their manufacturing method.

As commercialized white carbon, Carplex (trade name of Shionogi Pharmaceutical Co., Ltd.),
Nipseal (product name of Nippon Silica Industry Co., Ltd.), Tokushir (product name of Tokuyama Soda Co., Ltd.), Microcell (product name of Johnsmanville Corporation), Zonolite (product name of Onoda Chemical Co., Ltd.), Fluorite (trade name of Tokuyama Soda Co., Ltd.) and the like.

Depending on the brand, these white carbons include acidic, neutral and basic ones. The basic white carbon in the present invention has a hydrogen ion exponent of 8 or more, more preferably 9.5 or more, when the dispersion liquid is 10 wt% with pure water.

The herbicidal composition of the present invention comprises a sulfonylurea herbicidally active compound in an amount of 0.05 to 50% by weight,
Other herbicidally active compounds may be blended in the range of 1 to 60% by weight and basic white carbon in the range of 2 to 40% by weight to prepare wettable powders, fine granules, granules and granular wettable powders.

Examples of the diluent include clay, talc, diatomaceous earth, bentonite, calcium carbonate and the like.

As the surface active agent, nonionic surface active agents such as polyoxyethylene alkyl allyl ether, polyoxyethylene styryl phenyl ether, polyoxyethylene sorbitan fatty acid ester, and alkyl sulfonates, alkyl allyl sulfonates, Ionic surfactants such as alkyl sulfate ester salt, lignin sulfonate, alkyl naphthalene sulfonate formalin condensate, polyoxyethylene alkyl allyl ether sulfate, alkyl amine salt, dialkyl sulfosuccinate, polycarboxylate, etc. can give.

[0024]

EXAMPLES Next, the effect of preventing the decomposition of the active ingredient in the herbicidal composition of the present invention will be described with reference to Examples and Test Examples. The numbers in the formulation examples are parts by weight. It should be noted that sodium dodecylbenzenesulfonate is a surfactant and is one of the alkylallylsulfonates, and is shown by the abbreviation DBS below.

Example 1 Wettable powder Compound A 8 parts Compound C 60 parts Sodium lignin sulfonate 3 parts Polyoxyethylene alkylaryl ether sulphate 4 parts Carplex # 1120 (Shionogi Pharmaceutical Co., Ltd.) 17 parts Clay 8 parts Mix each component and use Jet omizer 0101
(Manufactured by Seishin Enterprise Co., Ltd.) to obtain a wettable powder.

Example 2 Wettable powder Compound B 8 parts Compound C 60 parts Sodium lignin sulfonate 3 parts Polyoxyethylene alkylaryl ether sulphate 4 parts Carplex # 1120 (Shionogi Pharmaceutical Co., Ltd.) 17 parts Clay 8 parts Mix each component and use Jet omizer 0101
(Manufactured by Seishin Enterprise Co., Ltd.) to obtain a wettable powder.

Example 3 Wettable powder Compound B 8 parts Compound C 60 parts Sodium lignin sulfonate 3 parts Polyoxyethylene alkylaryl ether sulphate 4 parts Microcell E (manufactured by Johnsmanville Corporation) 17 parts Clay 8 parts Each of the above components Mix and jet omizer 0101
(Manufactured by Seishin Enterprise Co., Ltd.) to obtain a wettable powder.

Example 4 Wettable powder Compound B 8 parts Compound C 60 parts Sodium lignin sulfonate 3 parts Polyoxyethylene alkylaryl ether sulphate 4 parts Zonolite A (manufactured by Onoda Chemical Co., Ltd.) 17 parts Clay 8 parts Each of the above Mix the ingredients and jet omizer 0101
(Manufactured by Seishin Enterprise Co., Ltd.) to obtain a wettable powder.

Example 5 Wettable powder Compound B 8 parts Compound C 60 parts Sodium lignin sulfonate 3 parts Polyoxyethylene alkylaryl ether sulfate 4 parts Fluorite R (manufactured by Tokuyama Soda Co., Ltd.) 17 parts Clay 8 parts Each of the above Mix the ingredients and jet omizer 0101
(Manufactured by Seishin Enterprise Co., Ltd.) to obtain a wettable powder.

Example 6 Wettable powder Compound B 8 parts Compound C 60 parts Sodium lignin sulfonate 3 parts Polyoxyethylene alkylaryl ether sulphate 4 parts Tokseal AL-1 (manufactured by Tokuyama Soda Co., Ltd.) 17 parts Clay 8 parts Mix each component and use Jet omizer 0101
(Manufactured by Seishin Enterprise Co., Ltd.) to obtain a wettable powder.

Example 7 Granules Compound A 0.2 parts Compound C 5.0 parts Carplex # 100 30.0 parts DBS 3.0 parts Sodium lignin sulfonate 5.0 parts Bentonite 20.0 parts Clay 36.8 Part After mixing the above components, after kneading by adding an appropriate amount of water,
The mixture was granulated by an extrusion granulator equipped with a screen having a pore diameter of 0.8 mm, dried at 50 ° C. for 2 hours, and sized to obtain granules.

Example 8 Granules Compound B 0.2 parts Compound C 5.0 parts Carplex # 108 30.0 parts DBS 3.0 parts Sodium lignin sulfonate 5.0 parts Bentonite 20.0 parts Clay 36.8 Part After mixing the above components, after kneading by adding an appropriate amount of water,
The mixture was granulated by an extrusion granulator equipped with a screen having a pore diameter of 0.8 mm, dried at 50 ° C. for 2 hours, and sized to obtain granules.

Comparative Example 1 Wettable powder Compound B 8 parts Compound C 60 parts Sodium lignin sulfonate 3 parts Polyoxyethylene alkylaryl ether sulphate 4 parts Carplex # 80 (Shionogi Pharmaceutical Co., Ltd.) 17 parts Clay 8 parts Above Mix each component and use Jet omizer 0101
(Manufactured by Seishin Enterprise Co., Ltd.) to obtain a wettable powder.

Comparative Example 2 Granules Compound B 0.2 parts Compound C 5.0 parts Carplex # 80 (Shionogi Pharmaceutical Co., Ltd.) 30.0 parts DBS 3.0 parts Sodium lignin sulfonate 5.0 parts Bentonite 20.0 parts Clay 36.8 parts After mixing the above components, adding an appropriate amount of water and kneading,
The mixture was granulated by an extrusion granulator equipped with a screen having a pore diameter of 0.8 mm, dried at 50 ° C. for 2 hours, and sized to obtain granules.

Test Example 1 Measurement of hydrogen ion index of white carbon Pure water was placed in a hard Erlenmeyer flask, boiled for 10 minutes, blocked with carbon dioxide and cooled to about 20 ° C. This pure water 90
In a 200 ml flask with a co-inspection, 10 g of a white carbon sample was immediately added, and the bottle was sealed and shaken for 1 minute, and then left standing for 5 minutes. Without crushing this, an electrode was put in the liquid and the hydrogen ion concentration was measured. For the measurement, a glass electrode type hydrogen ion concentration meter F15 [manufactured by Horiba Ltd.] was used. The results are shown in Table 1.

[0036]

[Table 1] Table 1 ──────────────────────────── White carbon type Hydrogen ion index ───────── ──────────────────── Carplex # 80 5.6 Carplex # 100 9.8 Carplex # 1120 10.8 Tokseal AL-1 9.6 Nipseal NA 10.0 Microcell E 8.4 Zonolite A 9.8 Fluorite R 8.5 ──────────────────────────────

Test Example 2 The various preparations produced in the above Examples and Comparative Examples were placed in glass sample bottles with an inner stopper and stored in a constant temperature bath at 40 ° C. for 30 days, and then the active ingredients were analyzed by reverse phase high performance liquid chromatography. did. The results are shown in Table 2. The decomposition rate of the active ingredient was calculated by the following formula.

Decomposition rate (%) = (1−a / b) × 100 where a: content of active ingredient after storage (%) b: content of active ingredient immediately after production (%)

[0039]

[Table 2] Table 2 ─────────────────────────────────── Decomposition of the used sulfonylurea-based white carbon compounds Rate (%) ────────────────────────────────── Example 1 Carplex # 1120 3.3 2 Car Plex # 1120 2.9 3 Microcell E 18.4 4 Zonolite A 16.7 5 Fluorite R 12.6 6 Tokseal AL-1 4.5 7 Carplex # 100 3.0 Comparative Example 1 Carplex # 80 26 4 2 Carplex # 80 30.4 ───────────────────────────────────

As shown in the above test result 2, the sulfonylurea compound was decomposed largely in the case of the preparation containing the neutral or acidic white carbon. However, when basic white carbon was added, the decomposition could be prevented as much as possible. In addition, other herbicides were stable in all formulations and no decomposition was observed.

[0041]

EFFECTS OF THE INVENTION By using basic white carbon, it becomes possible to prevent decomposition of sulfonylurea herbicidally active compounds.

Claims (5)

[Claims] 1. A sulfonylurea herbicidally active compound,
A solid herbicidal preparation characterized by containing basic white carbon in a mixed herbicide comprising one or more other herbicidal active compounds (excluding dinitroaniline-based herbicidally active compounds) 2. The sulfonylurea herbicidal active ingredient is N
The herbicidal solid preparation according to claim 1, which is-[(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -4-ethoxycarbonyl-1-methylpyrazole-5-sulfonamide. 3. A sulfonylurea herbicidal active ingredient is N
The herbicidal solid preparation according to claim 1, which is-[(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -3-chloro-4-methoxycarbonyl-1-methylpyrazole-5-sulfonamide. 4. A basic white carbon having a hydrogen ion index of 8 or more when made into a dispersible liquid of 10% by weight of pure water is contained.
Herbicidal solid formulation described 5. The herbicidal solid preparation according to claim 4, wherein the content of basic white carbon is 2 to 40% by weight based on the solid preparation.