JPH0517313A - Herbicide composition for paddy field - Google Patents

Abstract

PURPOSE:To obtain the subject excellent composition by combining S-(1-methyl-1- phenylethyl) piperidine-1-carbothioate with a specific 3,5-di-t-butyl-4- hydroxybenzylphosphone derivative. CONSTITUTION:The objective herbicide composition for paddy field is produced by combining (A) S-(1-methyl-1-phenylethyl)piperidine-l-carbothioate with (B) at least one kind of compounds of formula (R is 1-8C alkyl, alkenyl, halogen or alkoxy-substituted alkyl), e.g. dimethyl 3,5-di-tert-butyl-4-hydroxybenzy1 phosphonate. The combined use of the components reduces the amount of thiol carbamate compound, prolongs the durable period for killing gramineous weeds and expands the application period of the agent. The amount of the component B is 0.05-1 pt.wt. (preferably 0.1-0.6 pts.wt.) based on 1 pt.wt. of the component A.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a herbicide composition for paddy fields.

[0002]

2. Description of the Related Art Hitherto, various compounds such as thiol carbamate type and acetamide type have been developed as herbicides for grass weeds occurring in paddy fields. These compounds are widely used as herbicides for paddy fields as a single agent or a mixture agent, and play an important role in labor saving of agricultural work and improvement of productivity.

For example, S- (1-methyl-1-phenylethyl) piperidine-1-carbothioate [see Japanese Patent Publication No. 56-36167], which is known as a thiol carbamate compound, is a selective compound between rice and fly. It is widely used as a single agent or a mixed agent as a herbicide that is excellent in and is highly safe for peripheral field crops and seafood. However, in consideration of the diversification of paddy field farming work in recent years and the impact on the environment, it is desired to reduce the amount of applied chemicals as much as possible and to improve the herbicidal performance such as expanding the appropriate treatment period and extending the effect duration. ..

[0004]

Therefore, the present inventors have reduced the dose of the above-mentioned thiol carbamate compound, which is an active ingredient for weed killing action of grasses, and extending and treating the duration of grass weed killing effect. As a result of repeated studies for the purpose of expanding the appropriate period, it was found that the above object can be achieved by combining such a thiol carbamate compound with a certain substituted benzylphosphonic acid derivative, and the present invention It came to completion.

[0005]

According to the present invention, therefore, (A) S- (1-methyl-1-phenylethyl) piperidine-1-carbothioate (hereinafter referred to as "compound A").
And (B) the following general formula (I)

[Chemical 2] (Wherein R represents a linear or branched alkyl group or alkenyl group having 1 to 8 carbon atoms, or an alkyl group substituted with a halogen atom or an alkoxy group). Provided is a herbicide composition for paddy fields, which comprises at least one of -butyl-4-hydroxybenzylphosphonic acid derivative (hereinafter sometimes referred to as "compound B group").

The above-mentioned "compound A" used in the herbicidal composition of the present invention is a known compound and is described in detail in, for example, Japanese Patent Publication No. 56-36167. Further, the above-mentioned "Compound B group" is also a known compound and is known to be useful as a stabilizer for polymer compounds such as polypropylene, polyamide and polyurethane (German Patent No. 2,222,708; US Patent No. No. 3,280,070), it has been unpredictable and unpredictable that it could be incorporated into a herbicide to increase its herbicidal effect.

"Compound B which can be used in the present invention
Representative examples of the "group" are as follows. Compound No. 1: Dimethyl 3,5-di-tert-butyl-4-hydroxybenzylphosphonate No. 2: Diethyl 3,5-di-tert-butyl-4-hydroxybenzylphosphonate No. 3: Di-n-propyl 3,5-di-tert-butyl-
4-hydroxybenzylphosphonate

No. 4: Di-iso-propyl 3,5-di-
tert-Butyl-4-hydroxybenzylphosphonate No. 5: di-n-butyl 3,5-di-tert-butyl-4
-Hydroxybenzylphosphonate No. 6: di-iso-butyl 3,5-di-tert-butyl-
4-hydroxybenzylphosphonate

No. 7: Di-sec-butyl 3,5-diter
t-Butyl-4-hydroxybenzylphosphonate No. 8: di-iso-amyl 3,5-di-tert-butyl-
4-Hydroxybenzylphosphonate No. 9: di-n-octyl 3,5-di-tert-butyl-
4-hydroxybenzylphosphonate

No. 10: Di (chloroethyl) 3,5-di-tert-butyl-4-hydroxybenzylphosphonate No. 11: Di (β-methoxyethyl) 3,5-di-tert
-Butyl-4-hydroxybenzylphosphonate No. 12: di (β-ethoxyethyl) 3,5-di-tert
-Butyl-4-hydroxybenzylphosphonate No. 13: diallyl 3,5-tert-butyl-4-hydroxybenzylphosphonate

The compounding ratios of the "compound A" and the "compound B group" in the composition of the present invention are not necessarily strictly limited, and the application place of the final herbicidal composition, the applicable crop, the applicable object It can be varied over a wide range depending on the weeds, the time of application, etc., but generally the former "Compound A" 1
0.05 to 1 part by weight of "Compound B group" with respect to parts by weight,
It is suitable to mix it in a proportion of preferably 0.1 to 0.6 parts by weight.

When the composition of the present invention is used in combination with other herbicides, the herbicide species to be controlled can be further expanded, the suitable treatment period width can be expanded, and the dosage can be reduced. Examples of the herbicide which can be used by mixing with the composition of the present invention include N selected from the group of amide compounds.
-(1,1-Dimethylbenzyl) -2-brom-tert-butylacetamide (generic name: bromobutide), 2-benzothiazol-2-yloxy-N-methylacetanilide (generic name: mefenacet), 3,4-dichloro Propionanilide (generic name: propanil), 2-chloro-2,
6-diethyl-N- (butoxymethyl) acetanilide
(Generic name: butachlor), 2-chloro-2,6-diethyl-N- (n-propoxyethyl) acetanilide (generic name: pretilachlor);

1-selected from the group of urea compounds
(α, α-Dimethylbenzyl) -3- (4-methylphenyl) urea (generic name: Daimlon), 1- (α, α-dimethylbenzyl) -3- (2-chlorobenzyl) urea (code number: JC -940);

2,4-dichloro-1- (4-nitrophenoxy) selected from the group of diphenyl ether compounds
Benzene (generic name: nitrophene), 2,4,6-trichloro-1- (4-nitrophenoxy) benzene (generic name: chloronitrophene), 2,4-dichloro-1- (3-methoxy-4-nitrophenoxy) ) Benzene (generic name: clomethoxynil), methyl-5- (2,4-dichlorophenoxy) -2-nitrobenzoate (generic name: bifenox);

2,4-bis (ethylamino) -6-methylthio-1,3, selected from the group of triazine compounds
5-triazine (generic name: cimetrin), 2,4-bis (isopropylamino) -6-methylthio-1,3,5-triazine (generic name: promethrin), 2-methylthio-4-
Ethylamino-6- (1,2-dimethylpropylamino)
-1,3,5-triazine (generic name: dimetamethrin);

O-selected from the group of organic phosphorus compounds
Ethyl-O- (2-nitro-5-methylphenyl) -N-
sec-Butylphosphoroamidothioate (generic name: butamiphos), O, O-diisopropyl-S- (2-benzenesulfonylaminoethyl) phosphorodithioate (generic name: SAP), S- (2-methylpiperidine-
1-yl) carbonylmethyl-O, O-dipropylphosphorodithioate (generic name: piperophos);

Methyl-2- [3- (4,6-dimethoxypyrimidin-2-yl) ureidosulfonylmethyl] benzoate (general name: bensulfuron-methyl) selected from the group of sulfonylurea compounds;

S- (4-chlorobenzyl) -N, N-diethylthiolcarbamate (general name: ventiocarb) selected from the group of carbamate compounds, S-ethylhexahydro-1H-azepine-1-carbothioate
(General name: molinate), S-benzyl-N-ethyl-N
-(1,2-dimethylpropyl) thiol carbamate (generic name: esprocarb);

2 selected from the group of phenoxy compounds
-(2,4-Dichloro-3-methylphenoxy) propionanilide (generic name: clomeprop), S-ethyl-4
-Chloro-2-methylphenoxythioacetate (generic name: phenothiol), 2- (2-naphthoxy) propionanilide (generic name: naproanilide);

4-selected from the group of diazine compounds
(2,4-dichlorobenzoyl) -1,3-dimethylpyrazol-5-yl-p-toluenesulfonate (generic name:
Pyrazolate), 1,3-dimethyl-4- (2,4-dichloro-3-methylbenzoyl) -5- (4-methylphenacyloxy) pyrazole (generic name: benzophenap), 1,
3-dimethyl-4- (2,4-dichlorobenzoyl) -5
-Phenacyloxypyrazole (generic name: pyrazoxifene) and the like can be mentioned.

The blending ratio of these herbicides and the composition of the present invention is not necessarily strictly limited, and the application place of the final herbicidal composition, the application crop, the application weed, the application time, etc. It can be varied over a wide range according to.

When the composition of the present invention is actually used as a herbicide, the above-mentioned active ingredient is used as a solid or liquid carrier or diluent known per se, a surfactant or other auxiliaries for formulation, and a method known per se. It is possible to prepare a formulation form usually used as a pesticide, for example, granules, emulsions, wettable powders, flowable formulations and the like.

As solid carriers used in the production of herbicides, clays represented by kaolinite group, montmorillonite group, illite group or polygloskite group, more specifically, pyrophyllite, attapulgite, sepiolite, kaolinite, Inorganic substances such as bentonite, saponite, vermiculite, mica, talc and gypsum, calcium carbonate, dolomite, diatomaceous earth, calcite, magnesium lime, apatite, zeolite, anhydrous silicic acid, synthetic calcium silicate: soybean powder, tobacco Plant organic substances such as flour, walnut flour, wheat flour, wood flour, starch, crystalline cellulose; coumarone resin, petroleum resin,
Examples thereof include synthetic or natural polymer compounds such as alkyd resins, polyvinyl chloride, polyalkylene glycols, ketone resins, ester gums, cobal gums, dumbamar gums; waxes such as carnauba wax and beeswax, and urea.

Suitable liquid carriers include, for example, paraffinic or naphthenic hydrocarbons such as kerosene, mineral oil, spindle oil and white oil; aromatic hydrocarbons such as xylene, ethylbenzene, cumene and methylnaphthalene; dioxane and tetrahydrofuran. Such ethers; ketones such as methyl ethyl ketone, diisobutyl ketone, cyclohexanone, acetophenone, isophorone; esters such as ethyl acetate, amyl acetate, ethylene glycol acetate, diethylene glycol acetate, dibutyl maleate, diethyl succinate; n-hexanol, ethylene Alcohols such as glycol, diethylene glycol, cyclohexanol, and benzyl alcohol; ethylene glycol ethyl ether, ethylene glycol phenyl ether Ether, diethylene glycol ethyl ether, ether alcohols such as diethylene glycol butyl ether; dimethylformamide, polar solvents or water such as dimethyl sulfoxide.

In addition, emulsification, dispersion, wetting of the active ingredient,
Surfactants and other auxiliary agents can be used for the purpose of spreading, binding, controlling disintegration, stabilizing active ingredient, improving fluidity, and preventing rust. Examples of surfactants used include:
Nonionic, anionic, cationic and zwitterionic compounds can be used, but usually nonionic and / or anionic compounds are used.

Suitable nonionic surfactants are, for example, compounds obtained by polymerizing and adding ethylene oxide to higher alcohols such as lauryl alcohol, stearyl alcohol and oleyl alcohol; and ethylene oxide being polymerized and added to alkylphenols such as isooctylphenol and nonylphenol. Compounds: Compounds obtained by polymerizing addition of ethylene oxide to alkylnaphthols such as butylnaphthol and octylnaphthol; Compounds obtained by polymerizing addition of ethylene oxide to higher fatty acids such as palmitic acid, stearic acid and oleic acid: amines such as dodecylamine and stearic acid amide A compound obtained by polymerizing addition of ethylene oxide to ethylene; a higher fatty acid ester of a polyhydric alcohol such as sorbitan and a compound obtained by polymerizing addition of ethylene oxide thereto; ethylene Kishido and propionic oxide compound was block polymerized addition, and the like.

Suitable anionic surfactants include, for example, alkyl sulfate salts such as sodium lauryl sulfate and oleyl alcohol sulfate amine salt; alkyl such as sodium sulfosuccinate dioctyl ester and sodium 2-ethylhexenesulfonate. Sulfonates; aryl sulfonates such as sodium isopropyl naphthalene sulfonate, sodium methylenebisnaphthalene sulfonate, sodium lignin sulfonate, sodium dodecylbenzene sulfonate, and the like.

Further, the composition of the present invention contains casein, gelatin, for the purpose of improving the performance of the preparation and enhancing the herbicidal effect.
High molecular compounds such as albumin, glue, lignin sulfonate, alginate, gum arabic, carboxymethyl cellulose, methyl cellulose, hydroxyethyl cellulose, polyvinyl alcohol, polyvinylpyrrolidone, and polysaccharides and other auxiliary agents can be used together. The above carriers and various auxiliary agents can be appropriately used alone or in combination depending on the purpose in consideration of the dosage form of the preparation, the application scene, and the like.

The content of the active ingredient in the composition of the present invention in the various dosage forms thus obtained varies depending on the dosage form, but is, for example, 1 to 90% by weight, preferably 7 to 40% by weight. Can be In the case of a wettable powder, for example, it usually contains 25 to 90% by weight of the active ingredient,
The balance is a solid carrier and a dispersion wetting agent, and if necessary, a protective colloid agent, a defoaming agent and the like are added.

In the case of granules, for example, the active ingredient is usually 1 to
The content is 35% by weight, and the rest is a solid carrier and a surfactant. The active ingredient is uniformly mixed with the solid carrier, or is fixed or adsorbed uniformly on the surface of the solid carrier, and the particle diameter is about 0.2 to 1.5 mm. In the case of a flowable agent, for example, the active ingredient is usually 5
It is contained in an amount of 50% by weight, contains 3 to 10% by weight of a dispersion wetting agent, and the balance is water, and if necessary, a protective colloid agent, a preservative, an antifoaming agent and the like are added.

The appropriate application amount of the composition of the present invention prepared as described above cannot be unconditionally defined due to differences in meteorological conditions, soil conditions, drug formulation, target crops, target weeds, application time, application method and the like. Usually, 0.1 to 10 kg per hectare, based on the total amount of active ingredients, preferably 0.1.
A range of 2-4 kg is suitable. Furthermore, the composition of the present invention can also be used as a labor-saving control agent by appropriately adding an insecticide, a bactericide, a plant growth regulator and the like. Next, the present invention will be described in more detail with reference to Examples and Comparative Examples.

[0032]

【Example】

Example 1 Preparation of preparation No. 1 (granule) Compound A 10% by weight Compound B (Compound No. 1) 2% by weight White carbon 10% by weight Bentonite 30% by weight Talc 44% by weight Lignin sulfonic acid 3% by weight Lauryl sulfate Sodium 1% by weight

After mixing the components in the above mixing ratio, an appropriate amount of water was added and kneaded, and granulated using a usual extrusion granulator. Then, it was dried and further sieved (14 to 32 mesh) to obtain granules. In the same manner as described below, the compounding ratios of "Compound A" and "Compound B" were variously changed, and the total amount was adjusted by increasing or decreasing the compounding amount of talc to obtain Granules of Preparation Nos. 2 to 30. Table 1 shows the compounding ratio of each component of these preparations.

[0034]

TABLE 1 Compounding ratio in Table 1 formulation components (by weight%) No. Compound A Compound B WC BN TC LS SL 2 8 (No.1) 2 10 30 46 3 1 3 10 (No. 2) 2 10 30 44 3 1 4 8 (same as above) 2 10 30 46 3 1 5 7 (same as above) ) 2 10 30 47 3 1 6 6 (same as above) 2 10 30 48 3 1 7 10 (same as above) 1 10 30 45 3 1 8 8 (same as above) 1 10 30 47 3 1 9 7 (same as above) 1 10 30 48 3 1 10 6 (same as above) 1 10 30 49 3 1 11 10 (No. 3) 2 10 30 44 3 1 12 8 (same as above) 2 10 30 46 3 1 13 10 (No. 4) 2 10 30 44 3 1 14 8 (same as above) 2 10 30 46 3 1 15 7 (same as above) 2 10 30 47 3 1 16 6 (same as above) 2 10 30 48 3 1 17 10 (No. 5) 2 10 30 44 3 1 18 8 (same as above) 2 10 30 46 3 1 19 10 (No. 6) 2 10 30 44 3 1 20 8 (same as above) 2 10 30 46 3 1 21 10 (No. 10) 2 10 30 44 3 1 22 8 (same as above) 2 10 30 46 3 1 23 10 (No. 11) 2 10 30 44 3 1 24 8 (same as above) 2 10 30 46 3 1 25 7 (same as above) 2 10 30 47 3 1 26 10 (No, 12) 2 10 30 44 3 1 27 8 (same as above) 2 10 30 46 3 1 28 7 (same as above) 2 10 30 47 3 1 29 10 (No. 13) 2 10 30 44 3 1 30 8 (same as above) 2 10 30 46 3 1 Above In Table 1, C is white carbon, BN bentonite, TC talc, LS lignin sulfonate, SL represents sodium lauryl sulphate.

Comparative Example Preparation of formulation No. 31 (granule) Compound A 10% by weight White carbon 10% by weight Bentonite 30% by weight Talc 46% by weight Lignin sulfonic acid 3% by weight Sodium lauryl sulfate 1% by weight

After mixing the components in the above mixing ratio, an appropriate amount of water was added and kneaded, and the mixture was granulated using an ordinary extrusion granulator. Then, it was dried and further sieved (14 to 32 mesh) to obtain granules. In the same manner as above, the compounding ratio of "Compound A" was variously changed, and the total amount was adjusted by increasing or decreasing the compounding amount of talc to obtain Granules of Preparation Nos. 32-35. Further, in the same manner, Formulation Nos. 36 to 45 containing "Compound B" in place of "Compound A" were also obtained. Table 2 shows the compounding ratio of each component of these preparations.

[0037]

TABLE 2 mixing ratio in Table 2 Formulation components (wt%) No. Compound A Compound B WC BN TC LS SL 32 9 0 10 30 47 3 1 33 8 0 10 30 48 3 1 34 7 0 10 30 49 3 1 35 6 0 10 30 50 3 1 36 0 (No. 1) 2 10 30 54 3 1 37 0 (No. 2) 2 10 30 54 3 1 38 0 (No. 3) 2 10 30 54 3 1 39 0 (No. 4) 2 10 30 54 3 1 40 0 (No. 5) 2 10 30 54 3 1 41 0 (No. 6) 2 10 30 54 3 1 42 0 (No. 10) 2 10 30 54 3 1 43 0 (No. 11) 2 10 30 54 3 1 44 0 (No. 12) 2 10 30 54 3 1 45 0 (No. 13) 2 10 30 54 3 1 In the above Table 2, WC is white carbon, BN is bentonite, TC is talc, LS is lignin sulfonic acid, and SL is sodium lauryl sulfate. Represents.

[0038]

[Effects of the Invention] When "Compound A", which is the active ingredient of the composition of the present invention, is applied to a paddy field, the effect of killing soil and grass weeds gradually disappears. In the composition containing the “compound B group” of the present invention, the decomposition of the “compound A” in the paddy field is suppressed, so that the concentration of the “compound A” in water continues at a high concentration. As a result, it has become possible to reduce the amount of applied drug, extend the duration of weed dying of grasses, and expand the suitable treatment period.

The composition of the present invention has no phytotoxicity to rice and has a low dosage of grass weeds such as Nobie that occur in paddy fields.
In addition, it is an excellent herbicide for controlling weeds of grass family, which can be surely controlled over a wide range of suitable treatment period and which does not allow later development. Further, by combining the composition of the present invention with another herbicide, the weeds to be controlled can be widened, and a labor-saving herbicide that can be surely controlled by one treatment can be obtained.

The effects of the present invention will be described below with reference to test examples. Test Example 1 (Treatment Leaf Treatment Test) 1 / 5000a Wagner pot was filled with paddy field soil and chemical fertilizer, an appropriate amount of water was added, and the mixture was thoroughly stirred, and water was added to make a flooded state of 3 cm. .. Next, two 2-leaf stage paddy rice seedlings, which had been grown in advance in a greenhouse, were transplanted as 2 strains per pot, and 2 strains were transplanted per pot, and a certain amount of Novier seeds were sown. At the 1st leaf stage, the 2nd leaf stage, and the 2.5th leaf stage after sowing, the granules obtained in Examples and Comparative Examples were sprayed at a dose of 3 kg / 10a. Twenty days after the chemical treatment, the herbicidal effect and the degree of damage to paddy rice were investigated. The results are shown in Table 3.

[0041]

[0042]

[0043]

[Table 3]

[0044]

[Table 4]

Test Example 2 (Residual Effect Test) A 170 cm ² plastic pot was filled with paddy soil, lightly scraped, then flooded to 3 cm and allowed to stand for 3 days. Then, the granules obtained in Examples and Comparative Examples were mixed with 3 kg / 10a.
Was treated so that Further, 10 seeds of Novier germinated seeds were sown in each pot. The seeding was carried out at 6 days, 5 days, 10 days, 15 days, 20 days, 25 days and 30 days after the drug treatment. The investigation was carried out 15 days after the seeding of each Novier germinated seed, and the herbicidal effect was determined according to the evaluation criteria of Test Example 1. The results are shown in Table 4.

[0046]

[Table 5]

[0047]

[Table 6]

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Yoshie Kirio 8-3-1 Chuo, Ami-machi, Inashiki-gun, Ibaraki Mitsubishi Petrochemical Co., Ltd. Tsukuba Research Institute (72) Inventor Takashi Kaji Ami-cho, Inashiki-gun, Ibaraki Chuo 8-3-1, Mitsubishi Petrochemical Co., Ltd. Tsukuba Research Institute

Claims (1)

Claims: (A) S- (1-methyl-1-phenylethyl) piperidine-1-carbothioate; and (B) the following general formula (I): (Wherein R represents a linear or branched alkyl group or alkenyl group having 1 to 8 carbon atoms, or an alkyl group substituted with a halogen atom or an alkoxy group). -Butyl-4-hydroxybenzylphosphonic acid derivative and at least one kind of herbicide composition for paddy fields.