JPS6251923B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to herbicides that exhibit excellent biological activity. For more details, the formula: benzthiazol-2-yloxy-acetic acid N-methylanilide represented by; The present invention relates to a herbicide characterized by containing α(2-naphthoxy)-propionanilide (hereinafter abbreviated as MT101) represented by the following as an active ingredient. The present inventors have conducted repeated research in order to develop a drug that exhibits excellent herbicidal activity and accurately controls a wide variety of weeds, and as a result, the present inventors have now discovered that the present inventors have demonstrated herbicidal activity against a wide variety of weeds. Like the benzthiazol-2-yloxy-acetic acid N-methylanilide shown by the above formula (), the above formula () exhibiting herbicidal activity
It was discovered that herbicidal activity was cooperatively and synergistically increased by mixing with MT101 shown by. It is therefore an object of the present invention to provide new mixtures, especially herbicides. When the herbicide of the present invention is used for weed control, when the concentration of benzthiazol-2-yloxy-acetic acid N-methylanilide shown by the above formula () is used as a single agent, it exhibits an accurate control effect. Even when used against young weed species, by using MT101 in combination, extremely pronounced synergistic and synergistic effects occur, resulting in a marked increase in selective weeding power against a wide variety of weeds, resulting in accurate control. was recognized. In the present invention, benzthiazol-2-yloxy-acetic acid N-methylanilide represented by the formula () is a compound having a physical constant of mp 118°C. The herbicide of the present invention has low toxicity to warm-blooded animals and has good selectivity for cultivated plants, that is, it does not cause harm to cultivated plants at normal concentrations, so it can be used as a herbicide for weed control. It can be conveniently used for. The herbicide of the present invention exhibits excellent selective control efficacy, particularly when used as a pre-emergence soil treatment agent for paddy field weeds and a foliage soil treatment agent. As described above, the mixture of the present invention is excellent in safety, exhibits outstanding herbicidal activity, and has a wide herbicidal spectrum. For example, paddy field weeds include: Botanical name Latin name Dicotyledonous plant Rotala indica Koehne Azena Lindernia procumbens
Philcox Ludwiga prostrata Roxburgh Potamogeton distinctus A.
Benn Chickweed Elatine triandra Schk Monocot barnyard millet Echinochloa crus-galli
Beauv.var Monochoria vaginalis Presl Eleocharis acicularis L. Eleocharis Kuroguwai Ohwi Cyperus diffoumis L. Cyperus serotinus Rottboel Sagittaria pygmaea Miq Alisma canaliculatum A.Br.
etBouche Firefly Soirpus juncoides Roxburgh
var., etc., and has the characteristic that it has no harmful effect on paddy rice. However, the applicability of the mixed active compounds of the invention is
It is effective not only against paddy field weeds, but also against upland weeds, weeds harmful to straw, etc., and weeds in fallow fields. The word weed here means in its broadest sense any plant that grows in undesirable locations. When using the herbicide of the present invention, it can be used directly as it is by diluting it with water, or it can be used in various formulations using pesticide auxiliaries by methods commonly used in the field of pesticide manufacturing. can. In actual use, these various formulations can be used directly or diluted with water to a desired concentration. Examples of agricultural chemical auxiliaries mentioned here include diluents (solvents, fillers, carriers), surfactants (solubilizers, emulsifiers, dispersants, wetting agents), stabilizers, and fixing agents. Solvents include water: organic solvents; hydrocarbons [e.g. naphtha, petroleum distillates (paraffin wax, kerosene,
light oil, medium oil, heavy oil), benzene, toluene, xylenes], halogenated hydrocarbons (e.g. chlormethylene, carbon tetrachloride, trichloroethylene,
ethylene chloride, ethylene dibromide, chlorobenzene chloroform], alcohols [e.g.
Methyl alcohol, ethyl alcohol, propyl alcohol, ethylene glycol], ethers [e.g. ethyl ether, ethylene oxide, dioxane], alcohol ethers [e.g. ethylene glycol monomethyl ether, etc.], ketones [e.g. acetone, isophorone, etc.] ], esters (eg, ethyl acetate, amyl acetate, etc.), amides (eg, dimethylformamide, dimethylacetamide, etc.), and sulfoxides (eg, dimethyl sulfoxide, etc.). Inorganic granules as fillers or carriers; sulfur, slaked lime, magnesium lime, gypsum, calcium carbonate, silica, perlite, pumice, calcite, diatomaceous earth, amorphous silicon oxide, alumina, zeolite,
Clay minerals (e.g. pyrophyllite, talcum, montmorillonite, beidellite, vermiculite, kaolinite, mica): Vegetable granules; Grain flour, starch, modified starch, sugar, glucose, crushed plant stems: Synthetic resins Powder; phenolic resin,
Examples include urea resin and vinyl chloride resin. Examples of the surfactant include anionic surfactants; alkyl sulfate esters [e.g., sodium lauryl sulfate, etc.], aryl sulfonic acids, [e.g., alkylaryl sulfonate, sodium alkylnaphthalene sulfonate], succinates, Polyethylene glycol alkylaryl ether sulfate salts: cationic surfactants; alkylamines, [e.g., laurylamine, stearyltrimethylammonium chloride, alkyldimethylbenzyl ammonium chloride, etc.], polyoxyethylene alkylamines: nonionic Surfactants; polyoxyethylene glycol ethers, [e.g., polyoxyethylene alkylaryl ethers and condensates thereof], polyoxyethylene glycol esters, [e.g., polyoxyethylene fatty acid esters], polyhydric alcohol esters, [For example, polyoxyethylene sorbitan monolaurate], ampholytic surfactant, etc. can be mentioned. Other examples include stabilizers and fixing agents (eg, agricultural soap, casein lime, sodium alginate, polyvinyl alcohol (PVA), vinyl acetate adhesive, acrylic adhesive). The mixed active compound of the present invention can be manufactured into various formulations by methods generally practiced in the agricultural chemical manufacturing field. Examples of formulation forms include emulsions, oils, wettable powders, suspensions, granules, powders, capsules, and the like. The herbicide of the present invention contains 0.001 of the above mixed active ingredients.
It can contain up to 100% by weight, preferably 0.005 to 95% by weight. In actual use, the various formulations and spray preparations described above (ready-to-use)
The content of the mixed active compound in the preparation is generally in the range from 0.01 to 95% by weight, preferably from 0.05 to 60% by weight. The content of these mixed active ingredients can be appropriately changed depending on the form of the preparation, the method of application, purpose, timing, location, weed growth status, etc. The herbicide of the present invention may be used in combination with other agricultural chemicals, such as insecticides, acaricides, fungicides, nematocides, antiviral agents, herbicides, plant growth regulators, attractants, etc. compounds, carbamate compounds, dithio (or thiol) carbamate compounds, organochlorine compounds, dinitro compounds, organic sulfur or metal compounds, antibiotics, substituted diphenyl ether compounds, urea compounds,
[triazine-based compound] or/and fertilizer etc. can also be made to coexist. Specifically, benzthiazol-2-yloxy-acetic acid N-methylanilide of the formula () is a herbicide other than TM101, which is the mixing partner, that is, a diphenyl ether herbicide [specifically, p -Nitrophenyl-2,4,6-trichlorophenyl ether, 2,4-dichlorophenyl p-nitrophenyl ether, 2,4-dichlorophenyl 3-methoxy 4-nitrophenyl ether, etc.], phenoxy-based herbicides agent [specifically, 4-
Chloro-o-tolyloxyacetic acid, 4-(4-chloro-o-tolyloxy)butyric acid, 2,4-dichlorophenoxyacetic acid, d,1-2-(4-chloro-o
-tolyloxy)propionic acid, etc.], urea-based herbicides [specifically, 1-(α,α-dimethylbenzyl)-3-p-tolylurea, etc.], triazine-based herbicides [specifically, 2, 4-bis(ethylamino)-6-methylthio-1,3,5-triazine, 2-methylthio-4-(1,2-dimethylpropylamino)-6-ethylamino-S-triazine, 2-methylthio-4 , 6-bis(isopropylamino)-S-triazine, etc.], diazine herbicides [specifically, 5-tert-butyl-3-
(2,4-dichloro-5-isopropoxyphenyl)-1,3,4-oxadiazolin-2-one, 3-isopropyl-1-H-2,1,3-benzothiadiazine-(4 )-3H-one-2,2-dioxide, etc.], dinitroaniline herbicides [specifically, α,α,α-trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine, etc. ], pyrazole herbicides [specifically, 4-
(2,4-dichlorobenzoyl)-1,3-dimethylpyrazol-5-yl-p-toluenesulfonate, etc.), and in the case of such a mixture, each It is possible to use a mixture in a dosage less than that of a single agent, and by mixing these, a synergistic effect appears, and a precise effect can be obtained for weed control, especially for weed control in paddy fields. Various formulations or ready-to-use preparations containing the mixed active ingredients according to the invention are available.
Preparation) can be carried out by the application methods commonly used in the agricultural chemical manufacturing field, such as spraying (e.g., dusting, water surface application), soil application (e.g., soil mixing), etc. Application amount per unit area from 0.1 to 10 Kg, preferably from 0.5 to 10 Kg of mixed active compound per hectare.
8Kg is used. However, in special cases it is possible, and sometimes even necessary, to exceed or fall below these ranges. The present invention contains the compound of formula () and MT101 as active ingredients, and a diluent (solvent and/or filler and/or carrier) and/or
Alternatively, a herbicidal composition containing a surfactant and, if necessary, a stabilizer, a fixing agent, etc. is provided. Furthermore, the invention provides for applying to weeds and/or their growth sites the mixed active compounds of the invention alone or in the presence of diluents (solvents and/or fillers and/or carriers) and/or surfactants and, if necessary, e.g. A method for controlling weeds is provided, which is applied in combination with a stabilizer, a stabilizer, and a fixing agent. EXAMPLES Next, the content of the present invention will be specifically explained with reference to Examples, but the present invention should not be limited thereto. Example 1 (granules) Compound of the above formula (), 2.5 parts, MT101, 5.0
Part, bentonite (montmorillonite), 32.5
1 part, talc (talc), 58 parts, and lignin sulfonate, 2 parts, add 25 parts of water, sludge well, and form 10 to 40 mesh granules using an extrusion granulator at 40 to 50°C. Dry to make granules. Sprinkle this on weeds and/or their growing areas. Example 2 (granules) Clay mineral particles with a particle size distribution of 0.2 to 2 mm, 85
5 parts of the compound of formula () dissolved in an organic solvent, 5 parts of MT101, 10, were placed in a rotating mixer and rotated.
After spraying on the powder to make it evenly wet, dry it at 40-50℃ to form granules. Sprinkle this on weeds and/or their growing areas. Example 3 (hydrating agent) Compound of the above formula (5 parts, MT101, 10 parts,
A mixture of powdered diatomaceous earth and powdered clay (1:5),
80 parts, sodium alkylbenzene sulfonate,
Two parts, a sodium alkylnaphthalene sulfonate formalin condensate, and three parts were ground and mixed to prepare a wettable powder. This is diluted with water and applied dropwise to weeds and/or their growing areas. The unexpectedly superior and remarkable effects of the mixed active compounds of the present invention can be seen from the following test results when used against various paddy weeds. Test Example 1 Preparation of test compound for control test against paddy field weeds by application in flooded sewage
It was granulated into rod-shaped particles with a length of 0.5 mm and a length of 1 to 3 mm. Composition ratio (total 100 parts) Each single active compound: 0.8 to 10 parts Polyoxyethylene alkyl phenyl ether: 2.5 parts Bennite: 30 parts Talc: 57.5 to 66.7 parts (The amount of the active ingredient can be adjusted by increasing or decreasing the amount of talc. Test method 1: Chemical treatment after rice transplantation The test field was plowed to a depth of 20 to 25 cm using a tractor according to the usual rice cultivation method.
Immediately after plowing, the field was flooded with water from an irrigation canal to a depth of 1 to 2 cm, and the first puddling was performed. One or two days after the first puddling, the area was further flooded to a depth of about 5 cm and the first puddling was carried out. Two days after the final plowing, the water depth in the field was adjusted to 2 to 3 cm, and a powered rice transplanter was used to
Rice seedlings grown in a special seedling box (15 days old, 2 to 2.5 days old)
3 to 5 leaves (plant height 15 to 17 cm) were transplanted per plant. Immediately after transplantation, the field was divided into 20 m ² (2 m x 10 m) sections using hard plastic sheets, and the water depth of the field was maintained at 3 to 5 cm for a long period of time. Three and 15 days after transplanting paddy rice, the compound prepared as described above was applied in water. Four weeks after application of the chemical, the control effect was investigated according to the criteria described below. The effectiveness is evaluated when compared to the untreated area. 5: Weed killing rate is 95% or more (death) compared to the untreated area. 4: Weed killing rate is 80% or more and less than 95% compared to the untreated area. 3: Weed killing rate is 50% compared to the untreated area. More than 80% 2: Herb killing rate in untreated area 30% or more but less than 50% 1: Herb killing rate in untreated area 10% or more but less than 30 0: Medicinal herb rate in untreated area less than 10% (no effect) Drug damage to paddy rice An evaluation of "0" indicates no drug damage. The test results are shown in Table 1. However, the compound [] in the compound column in each table indicates benzthiazol-2-yloxy-acetic acid N-methylanilide of the above formula (), and the symbols A, B, C, D,
E, F, and G indicate the following weeds. A: Nobie, B: Firefly, C: Konagi, D:
Broad-leafed weeds, E: Japanese lily, F: Japanese cypress, G: Japanese cypress.

[Table] The present invention, which has been explained in detail in the detailed description of the invention, is specifically summarized as follows. (1 set: benzthiazol-2-yloxy-acetic acid N-methylanilide represented by; A herbicide characterized by containing α-(2-naphthoxy)-propionanilide (hereinafter abbreviated as MT-101) represented by the following as an active ingredient. (2) A method for controlling weeds, which comprises applying an effective amount for controlling weeds of a mixed active compound of the compound of formula () and MT101 to weeds and/or their growing areas. (3) The mixed active compounds are used alone or combined with diluents (solvents and/or fillers and/or carriers) and/or surfactants and, if necessary, stabilizers, e.g.
By mixing with a fixing agent, the mixture
The pest control method according to item (2) above, which uses a prepared agent containing 0.01 to 95% by weight, preferably 0.05 to 60% by weight. (4) The pest control method according to item (2) above, wherein the applied amount of the mixed active compound is 0.1 to 10 kg, preferably 0.5 to 8 kg per hectare.

Claims (1)

[Claims] 1 Formula: Benzthiazol-2-yloxy-acetic acid N-methylanilide represented by the formula: A herbicide characterized by containing α-(2-naphthoxy)-propionanilide represented by as an active ingredient.