JP4777019B2 - Herbicidal composition - Google Patents

Description

  The present invention relates to a specific pyrazole derivative, 2,3-dihydro-3,3-dimethylbenzofuran-5-yl ethanesulfonate, 1- (3-chloro-4,5,6,7-tetrahydropyrazolo. The present invention relates to a herbicidal composition containing [1,5-a] pyridin-2-yl) -5- [methyl (prop-2-ynyl) amino] pyrazole-4-carbonitrile as an active ingredient and use thereof.

  At present, a large number of herbicides such as paddy field herbicides have been put into practical use and widely used as single agents and mixed agents. However, there are many kinds of weeds, and the germination and growth time of each weed is not uniform, and the generation of perennial weeds is particularly long. Therefore, it was very difficult to control all weeds with a single herbicide application.

  4- (2,4-dichlorobenzoyl) -1,3-dimethyl-5-pyrazolyl-p-toluenesulfonate (generic name pyrazolate), 2- [4- (2,4-dichlorobenzoyl) -1,3-dimethyl Pyrazol-5-yloxy] acetophenone (generic name pyrazoxifene) and 2- [4- (2,4-dichloro-m-toluoyl) -1,3-dimethylpyrazol-5-yloxy] -4′-methylacetophenone (general Pyrazole derivatives such as the name benzophenap; 2,3-dihydro-3,3-dimethylbenzofuran-5-yl ethanesulfonate (generic name benfrate); and 1- (3-chloro-4,5,6, 7-Tetrahydropyrazolo [1,5-a] pyridin-2-yl) -5- [methyl (prop-2-ynyl) amino] pyra Lumpur-4-carbonitrile (common name pyraclonil) is a known compound used for each of herbicides, are described in Non-Patent Document 1 and Patent Document 1.

Moreover, although the mixture of any one of a pyrazolate, a pyrazoxifene, or a benzophenap, and a benfrise is disclosed by patent document 2, the effect with respect to nobies and annual broad-leaved weeds of these mixtures is not enough. A mixture of pyrazolate, pyrazoxifene, or benzophenap and pyraclonil is disclosed in Patent Document 3, but the effect of these mixtures on Inu firefly and Sphagnum is not sufficient. A mixed agent of benfrate and pyraclonil is also disclosed in Patent Document 3, but the effect of this mixed agent on Urikawa and Omodaka is not sufficient.
WO94 / 08999 pamphlet JP-A-2-28101 Special Table 2000-500445 The Pesticide Manual 12th Edition 793-794, 797-798, 83, 71-72

  As a result of intensive studies to solve the problems of the above-described conventional herbicides, the present inventors have achieved excellent control by blending three kinds of specific pyrazole derivatives, benfrate and pyraclonil as active ingredients. While the effect was obtained, the present invention was completed by finding out that it is excellent in safety.

That is, the present invention
(A) 4- (2,4-dichlorobenzoyl) -1,3-dimethyl-5-pyrazolyl-p-toluenesulfonate (generic name pyrazolate), 2- [4- (2,4-dichlorobenzoyl) -1, 3-dimethylpyrazol-5-yloxy] acetophenone (generic name pyrazoxifene), and 2- [4- (2,4-dichloro-m-toluoyl) -1,3-dimethylpyrazol-5-yloxy] -4′-methyl At least one pyrazole derivative selected from acetophenone (generic name benzophenap);
(B) 2,3-dihydro-3,3-dimethylbenzofuran-5-yl ethanesulfonate (generic name benfrate);
(C) 1- (3-Chloro-4,5,6,7-tetrahydropyrazolo [1,5-a] pyridin-2-yl) -5- [methyl (prop-2-ynyl) amino] pyrazole- 4-carbonitrile (generic name: pyraclonyl)
And a herbicidal composition comprising the three herbicidal active compounds (hereinafter also referred to as “the herbicidal active compound of the present invention”) as an active ingredient.
The present invention also relates to a method for controlling weeds using the above herbicidal composition.

In the present invention, a synergistic effect is exhibited and an excellent control effect is obtained by using three kinds of herbicidal active compounds of at least one of the above pyrazole derivatives, benfrate and pyraclonyl. That is, germination and growth of weeds can be suppressed or weeds can be killed with a small amount of active ingredient and the number of uses.
In particular, in the present invention, the number of times of use can be reduced and the control effect can be maintained for a certain period of time, so that the work effort for controlling weeds can be reduced.
The herbicidal composition of the present invention has a broad herbicidal spectrum and can control many types of weeds including annual and perennial weeds. For example, various weeds that are problematic in paddy fields, for example, grass weeds such as Tainubie; broad-leaved weeds such as Azena, azeto pepper, kakashigusa, Mizohakobe, Abnomome, Himeisohagi, Konagi, etc .; It exhibits control activity against cyperaceae weeds; and Omodaka weeds such as Urikawa, Omodaka and Heramodaka.
Furthermore, the herbicidal composition of the present invention does not cause phytotoxicity to useful plants such as rice, and has excellent safety such as low toxicity to human livestock.

  The herbicidal composition of the present invention shows a synergistic control effect by containing at least one of the above-mentioned pyrazole derivatives and three herbicidally active compounds of benfrate and pyraclonil as active ingredients. A wide range of mixing ratios of these three herbicidal active compounds is observed. In the present invention, the mixing ratio of these three herbicidal active compounds can be varied over a wide range depending on the application area, target weed, application time, etc. of the herbicidal composition of the present invention. On the other hand, it is possible to mix Benfresate in a proportion of 0.01 to 100 parts by mass and Pyraclonil in a proportion of 0.01 to 100 parts by mass. In terms of obtaining an excellent control effect or safety, 0.1 to 10 parts by mass of benfrecetate and 0.05 to 5 parts by mass of pyraclonil are preferably mixed with 1 part by mass of the pyrazole derivative. It is more preferable to mix benfrate with 0.2-1 mass part and pyraclonil at a ratio of 0.1-0.5 mass part with respect to 1 mass part of the pyrazole derivative.

The pyrazole derivative used in the present invention is:
4- (2,4-dichlorobenzoyl) -1,3-dimethyl-5-pyrazolyl-p-toluenesulfonate (generic name pyrazolate),
2- [4- (2,4-Dichlorobenzoyl) -1,3-dimethylpyrazol-5-yloxy] acetophenone (generic name pyrazoxifene) and 2- [4- (2,4-dichloro-m-toluoyl)- 1,3-dimethylpyrazol-5-yloxy] -4′-methylacetophenone (generic name benzophenap)
It is three.
In the present invention, one or more of these pyrazole derivatives can be used. When two or more are used, the combination of these pyrazole derivatives is not particularly limited, but 4- (2,4-dichlorobenzoyl) -1,3-dimethyl-5- 5 is obtained in that an excellent control effect or safety is obtained. Pyrazolyl-p-toluenesulfonate (generic name pyrazolate) and 2- [4- (2,4-dichloro-m-toluoyl) -1,3-dimethylpyrazol-5-yloxy] -4′-methylacetophenone (generic name benzo A combination with fenap) is preferred.

  The composition of the present invention may be the active ingredient itself of the herbicidally active compound of the present invention, or may further contain other herbicidally active compounds, carriers, or other auxiliary agents as required.

  The herbicidal composition of the present invention may contain a herbicidal active compound other than the herbicidal active compound of the present invention in order to further broaden the herbicidal spectrum. For example, mefenacet, fentolazamide, oxadiclomephone, indanophan, caffentrol, molinate, beniocurve, anilophos, pyriminobacmethyl, pyriftalide, cihalohopbutyl, metamihop, pentoxazone, butachlor, pretilachlor, tenylchlor, cimethrin, dimetamethrin, MCPB, benzobicyclone, Examples include diimron, cumyllon, azimusulfuron, bensulfuron methyl, pyrazosulfuron, imazosulfuron, cyclosulfamuron, ethoxysulfuron, and penoxsulam.

  In the present invention, the carrier means a synthetic or natural inorganic or organic substance mixed in a herbicide to help the herbicidal active compound reach the plant or to facilitate storage, transportation or handling. means. In the present invention, a solid carrier and a liquid carrier can be used as the carrier.

Examples of the solid carrier include clays represented by the kaolinite group, montmorillonite group, attapulgite group, and the like; talc, mica, foliar, pumice, vermiculite, gypsum, dolomite, diatomaceous earth, magnesium lime, phosphorus lime, Inorganic substances such as zeolite, anhydrous silicic acid, synthetic calcium silicate, kaolin, bentonite, calcium carbonate; plant organic substances such as soybean powder, tobacco powder, walnut powder, wheat flour, wood flour, starch, crystalline cellulose; coumarone resin, Synthetic or natural polymer compounds such as petroleum resin, alkyd resin, polyvinyl chloride, polyalkylene glycol, ketone resin, ester gum, copal gum, dammar gum; waxes such as carnauba wax, paraffin wax and beeswax; or urea It is done.
Examples of the liquid carrier include paraffinic or naphthenic hydrocarbons such as kerosene, mineral oil, spindle oil, and white oil; aromatic hydrocarbons such as benzene, toluene, xylene, ethylbenzene, cumene, and methylnaphthalene; carbon tetrachloride, chloroform , Chlorinated hydrocarbons such as trichloroethylene, monochlorobenzene and chlorotoluene; ethers such as dioxane and tetrahydrofuran; ketones such as acetone, methyl ethyl ketone, diisobutyl ketone, cyclohexanone, acetophenone and isophorone; ethyl acetate, amyl acetate, ethylene glycol acetate , Esters such as diethylene glycol acetate, dibutyl maleate, diethyl succinate; methanol, hexanol, ethylene glycol, diethylene Alcohols such as recall, cyclohexanol and benzyl alcohol; ether alcohols such as ethylene glycol ethyl ether, ethylene glycol phenyl ether, diethylene glycol ethyl ether and diethylene glycol butyl ether; polar solvents such as dimethylformamide and dimethyl sulfoxide; or water .

  The herbicidal composition of the present invention contains a surfactant for the purposes of emulsification, dispersion, wetting, spreading, binding, disintegration control, stabilizing active ingredients, improving fluidity, preventing rust, promoting absorption into plants, and the like. be able to. This surfactant may be an ionic surfactant or a nonionic surfactant.

  Examples of the nonionic surfactant include ethylene oxide polymerized adducts of higher aliphatic alcohols such as sucrose esters of fatty acids, lauryl alcohol, stearyl alcohol, and oleyl alcohol; ethylene oxide polymerized adducts of alkylphenols such as isooctylphenol and nonylphenol. Ethylene oxide polymerization adducts of alkyl naphthols such as butyl naphthol and octyl naphthol; ethylene oxide polymerization adducts of higher fatty acids such as palmitic acid, stearic acid and oleic acid; oxidation of mono- or dialkyl phosphoric acids such as stearyl phosphate dilauryl phosphate Ethylene polymerized adduct; Oxidized ethylene polymerized adduct of higher aliphatic amines such as dodecylamine and stearamide; Higher fatty acid esters of polyhydric alcohols such as sorbitan and their oxidation Styrene polymerization adducts; and the like copolymers of ethylene oxide and propylene oxide.

Examples of the ionic surfactant include an anionic surfactant and a cationic surfactant.
Examples of the anionic surfactant include, for example, alkyl sulfate salts such as sodium lauryl sulfate and oleyl alcohol sulfate ester amine salt, fatty acid salts such as sodium dioctyl sulfosuccinate, sodium oleate and sodium stearate, isopropyl naphthalene sulfonic acid Examples thereof include alkylaryl sulfonates such as sodium, sodium methylenebisnaphthalene sulfonate, sodium lignin sulfonate, and sodium dodecylbenzene sulfonate.
Examples of the cationic surfactant include higher aliphatic amines, quaternary ammonium salts, and alkylpyridinium salts.

  The herbicidal composition of the present invention is, for example, gelatin, gum arabic, casein, albumin, glue, sodium alginate, polyvinyl for the purpose of improving the properties of the preparation or enhancing the biological effect. Alcohols, polymer compounds such as carboxymethylcellulose, methylcellulose, and hydroxymethylcellulose, thixotropic agents such as sodium polyphosphate and bentonite can be contained.

  The herbicidal composition of the present invention may contain, for example, a plant growth regulator, fungicide, insecticide, acaricide, nematicide or fertilizer.

  The herbicidal composition of the present invention is a pharmaceutical form usually used for herbicides, for example, powder, coarse powder, fine granules, granules, wettable powder, emulsion, aqueous suspension, granular wettable powder, oil suspension. It can also be used in the form of a preparation such as an agent and paddy throwing agent.

Said powder agent and coarse powder agent contain 0.1-25 mass parts of this invention herbicidal active compounds, for example, and a remainder is a solid support | carrier.
The above-mentioned wettable powder and granule wettable powder contain, for example, 1 to 90 parts by mass of the herbicidal active compound of the present invention, and the balance is a solid carrier and a dispersion wetting agent. And an antifoam agent is added. These preparations are suspended and dispersed in water when stirred in water.
The above-mentioned granules and fine granules contain, for example, 0.1 to 35 parts by mass of the herbicidal active compound of the present invention, and the remainder is mostly a solid carrier. The herbicidal active compound of the present invention is homogeneously mixed with the solid carrier, or is uniformly fixed or adsorbed on the surface of the solid carrier, and the particle diameter is usually 0.2 to 1.5 mm.
The above emulsion contains, for example, 1 to 70 parts by mass of the herbicidal active compound of the present invention, which contains 5 to 20 parts by mass of an emulsifier, and the remainder is a liquid carrier, and if necessary, a rust inhibitor. Other adjuvants such as are added.
The above aqueous suspension and oil suspension are, for example, those obtained by suspending or emulsifying the herbicidal active compound of the present invention in a water or high boiling point organic solvent using an appropriate surfactant. Depending on the condition, a thickener or the like is added to maintain the stability over time.
The above paddy throwing agent is prepared by formulating the herbicidally active compound of the present invention into an appropriate dosage form, for example, powder, granule, tablet, emulsion, bulk tablet, etc., and if necessary, water-soluble film or container. For example, when using these, several to several hundreds of them are scattered and used in the paddy field.

The herbicidal composition of the present invention can be used for controlling weeds.
The application period of the herbicidal composition of the present invention is usually before or after germination of weeds, preferably within about one month after germination, but is not particularly limited to these periods, and is not limited to the application region, target It can be changed as appropriate according to weeds, amount used, and the like.

Examples of the treatment method using the herbicidal composition of the present invention include soil treatment, foliage treatment or flooding treatment, but are not particularly limited to these treatment methods, application area, target weed, application time It can be changed as appropriate.
The soil treatment includes soil surface treatment, soil admixing treatment, etc., and the above-mentioned foliage treatment is applied to only weeds so as not to adhere to crops in addition to treatment such as spraying from above the plant body. Examples of the submerged treatment include spraying of granules and flowable agents and irrigation treatment on the water surface.
In the present invention, only one of the above processes may be performed, or a plurality of processes may be arbitrarily combined.

  The herbicidal composition of the present invention can effectively control weeds, for example, by treating with 1 g to 1000 g, preferably 10 g to 300 g of the herbicidal active compound of the present invention per 10a. However, the present invention is not limited to this, and can be appropriately changed depending on the application area, target weed, application time, treatment method, and the like.

  In the present invention, in order to control weeds, the herbicidally active compound of the present invention may be mixed and used as one preparation, or the herbicidally active compound of the present invention is not used as a mixed preparation, and at a predetermined ratio during use. Mixing, for example, tank mixing, may be used simultaneously. Alternatively, the herbicidally active compounds of the present invention may be used separately, that is, any of the herbicidally active compounds of the present invention may be used first, followed by other herbicidally active compounds of the present invention. The order and interval are not particularly limited.

  When using the herbicidal composition of this invention, it can also use together with a plant growth regulator, a fungicide, an insecticide, an acaricide, a nematicide, a fertilizer etc., for example.

  Hereinafter, the present invention will be specifically described with reference to formulation examples and test examples of the composition of the present invention, but the present invention is not limited thereto. In the following formulation examples, “%” indicates mass%.

(Formulation example 1)
Manufacture of wettable powder 10 parts by mass of pyrazolate, 2 parts by mass of pyraclonyl, 4.5 parts by mass of benferate, 10 parts by mass of Carplex # 80D (manufactured by Shionogi & Co., Ltd.), Gohsenol GL05-S (Nippon Synthetic Chemical Co., Ltd.) 2 parts by mass, New Coal 291PG (dioctylsulfosuccinate sodium salt, manufactured by Nippon Emulsifier Co., Ltd.) 0.5 parts by mass, Neogen Powder (Daiichi Kogyo Seiyaku Co., Ltd.) 5 parts by mass, Radiolite # 10 parts by mass of 200 (manufactured by Showa Chemical Industry Co., Ltd.) and 56 parts by weight of H derivative (manufactured by Keiwa Furnace Co., Ltd.) were sufficiently mixed. This mixture was pulverized with an air mill (SK-JET O MIZER model 0101, manufactured by Seishin Co., Ltd.) to obtain a mixed wettable powder.

(Formulation example 2)
Manufacture of Granules 61.22 parts by mass of pyrazolate, 0.85 parts by mass of New Coal 291PG and 37.93 parts by mass of water are mixed and pulverized to a particle size of about 2 μm with an attritor (Mitsui Mine Co., Ltd.). Obtained. 2 parts by mass of Toxanone (manufactured by Sanyo Chemical Co., Ltd.) was added to 98 parts by mass of the slurry and mixed to obtain slurry 2. 2.09 parts by mass of pyraclonyl, 2 parts by mass of sodium tripolyphosphate (manufactured by Mitsui Chemicals, Inc.), 1 (dextrin, manufactured by Nippon Starch Chemical Co., Ltd.) 1.5 parts by mass, bentonite (produced by Toyoshun Mining Co., Ltd.) 25 parts by mass, calcium carbonate calfin 600 (produced by Adachi Lime Co., Ltd.) 51.96 parts by mass Were mixed in a kneader (manufactured by Fuji Sangyo Co., Ltd., FM-NW-5 type), and further 17.45 parts by mass of slurry 2 was added and mixed. This mixture was extruded and granulated using Dome Gran (Fuji Paudal Co., Ltd., screen 1.0 mmφ). The obtained granulated product was dried with a shelf dryer (manufactured by Tabai Co., Ltd., PERFECT OVEN PS-222 type, 60 ° C.), and then sieved to 600 to 1190 μm to obtain base granules. Separately, Benfresate was weighed in a beaker and heated and melted on a hot plate (Heat Master manufactured by Toshiba Corporation). 4.5 parts by mass of the melted benfrate was absorbed and mixed with 95.5 parts by mass of the obtained base grain to obtain a mixed granule.

(Test Example 1)
Pest control effect and phytotoxicity test for transplanted rice paddy paddy soil mixed with broad-leaved weed (BLW; Azena, Mizojakobe) seeds is filled in a 1 / 10,000a pot, and after dormancy, dormant awakened Tainubie (ECH), Inu firefly (SCI) Seeded with a certain amount of seeds, planted tubers of urikawa (SAP), Omodaka (SAT), and Mitsugayatsuri (CYP) that were awakened to dormancy, and transplanted rice seedlings at 2.2 leaf stage (OS), and flooded Conditioned and grown in greenhouse. Three days after transplantation, the prescribed amount of wettable powder prepared according to Formulation Example 1 was diluted in water and treated with flooded soil once. After 25 days, the control effect and transplantation were performed according to the following criteria. The chemical damage to paddy rice was determined, and the results are shown in Table 1.
In addition, it tested simultaneously about the 2 types of mixture described in patent document 2 and patent document 3. FIG.

Judgment criteria Control effect 0: Growth inhibition rate 0-5%
1: Growth inhibition rate 6-15%
2: Growth inhibition rate 16-25%
3: Growth suppression rate 26-35%
4: Growth inhibition rate 36-45%
5: Growth inhibition rate 46-55%
6: Growth inhibition rate 56-65%
7: Growth inhibition rate 66-75%
8: Growth inhibition rate 76-85%
9: Growth suppression rate 86-95%
10: Growth inhibition rate 96-100%

Judgment criteria Chemical damage-: None ±: Minor +: Minor + ++: Moderate +++: Major +++++: Major

(Test Example 2)
Test of herbicidal effect against redwood After filling paddy field soil in a 1 / 10000a pot, tubers of awakened whitewood (SAT) were planted and grown in a greenhouse in a submerged state. Three days after transplantation, the prescribed amount of wettable powder prepared according to Formulation Example 1 is diluted in water, and then it is subjected to flooded soil treatment once. It was measured. Based on the measurement results, the herbicidal effect was calculated by the following formula and shown in Table 2.
(Herbicidal effect) = 100− (ratio of residual herb weight to untreated section).
Table 2 shows values (expected values) representing additive effects when two compounds are mixed using Colby's formula (Weeds 15, P20-22, 1967) from the calculated values of herbicidal effects. Also written. When the actual experimental result exceeds the expected value, it means a combination having a synergistic effect.
In addition, it tested simultaneously about the 2 types of mixture described in patent document 2 and patent document 3. FIG.

As is clear from Test Example 1 and Test Example 2, the herbicidal composition of the present invention in which three kinds of pyrazole derivatives, benfrate and pyraclonil were mixed was used when each single agent was used alone for the weeds tested. Compared with the case where two kinds are mixed or used, an excellent control effect was exhibited, and a synergistic effect exceeding expectation was recognized. Also, no phytotoxicity was observed on rice.
Thereby, by using the herbicidal composition of the present invention, weeds can be controlled with a smaller dose and a single use.

  Since the herbicidal composition of the present invention is excellent in controlling effect and safety as a herbicide, it is useful for controlling weeds such as residential land, railways, parks, parking lots, orchards, paddy fields, and upland fields. . In particular, it is useful as a herbicide for paddy fields.

Claims (2)

(A) 4- (2,4-dichlorobenzoyl) -1,3-dimethyl-5-pyrazolyl-p-toluenesulfonate, 2- [4- (2,4-dichlorobenzoyl) -1,3-dimethylpyrazole- 5-yloxy] acetophenone and at least one pyrazole derivative selected from 2- [4- (2,4-dichloro-m-toluoyl) -1,3-dimethylpyrazol-5-yloxy] -4′-methylacetophenone ,
(B) 2,3-dihydro-3,3-dimethylbenzofuran-5-yl ethanesulfonate;
(C) 1- (3-Chloro-4,5,6,7-tetrahydropyrazolo [1,5-a] pyridin-2-yl) -5- [methyl (prop-2-ynyl) amino] pyrazole- 4-carbonitrile,
A herbicidal composition containing as an active ingredient.   A method for controlling weeds, comprising using the herbicidal composition according to claim 1.