KR960007693B1 - Herbicidal agents - Google Patents

Abstract

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Description

Herbicide

The present invention relates to novel herbicidal active ingredient combinations of known O-ethyl S, S-diphenyl phosphorodithioate with known herbicidally active substances.

It is already known that O-ethyl S, S-diphenyl phosphorodithioate has agricultural fungicidal activity (Japanese Patent Publication No. 12,919 / 1969). In addition, certain active substances are already described in the known literature, The Pesticide Manual, 7th edition, 1983, published by the British Crop Protection Council. O-ethyl S, S-diphenyl phosphorodithioate has a particularly high fungicidal action against rice blasts but no herbicidal action, while certain known herbicidal active substances have individual average actions.

Efforts have been made to reduce the amount of active ingredient, increase herbicidal action and reduce fish-toxicity.

According to the present invention, (1) O-ethyl S, S-diphenyl phosphoro dithioate (ediffene force) of the structural formula (I) and (2) (a) haloacetamide of the general formula (II), ( b) thiol carbamate of formula (III), (c) 1- (α, α-dimethylbenzyl) -3- (4-methylphenyl) urea (daimone) and (d) of formula (IV) A novel active ingredient combination with at least one herbicidal active ingredient selected from the group consisting of S-2-methylpiperidinocarbonylmethyl O, O-dipropylphosphorodithioate of lost.

(Ediffenforce)

(Dime)

(여기에서, R₇은 수소원자 또는 알킬그룹을 나타내고 X는 수소 또는 할로겐 원자를 나타낸다)의 그룹을 나타내고, R₅및 R₆는 알킬 그룹을 나타내거나 N원자와 함께Wherein R ₁ and R ₂ each represent an alkyl group, R ₃ represents an alkoxyalkyl group, R ₄ represents an alkyl group, or

Wherein R ₇ represents a hydrogen atom or an alkyl group and X represents a hydrogen or halogen atom, and R ₅ and R ₆ represent an alkyl group or together with an N atom

를 나타낸다.

Indicates.

Surprisingly, the active ingredient combinations according to the invention exhibit substantially greater herbicidal activity than the above-mentioned known herbicidal active ingredients (a), (b), (c) or (d) itself, ie the known The combination of the fungicidal and non-herbicidal active ingredient (1) with the herbicidal active ingredient (2) produces a selected herbicidal effect which is particularly complimentary to non-weeds.

As mentioned above, O-ethyl S, S-diphenyl phosphorodithioate of formula (I) is already known (Japanese Patent Publication No. 12,919 / 1969).

In general station (II), R ₁ and R ₂ preferably represent an alkyl group having 1 to 3 carbon atoms, and R ₃ preferably represents a (C ₁ -C ₄ alkoxy)-(C ₁ -C ₂ alkyl) group Indicates.

Examples of haloacetamides of formula (II) include N-butoxymethyl-2-chloro-2 ', 5'-diethylacetanilide (butachloro), and Nm-propoxyethyl-2-chloro-2' , 6'-dietalacetyl anilide.

(여기에서, R₇은 수소원자 또는 메틸그룹을 나타내고, X는 수소 또는 할로겐 원자를 나타낸다)의 그룹을 나타내고, R₅및 R₆는 탄소수 2 내지 5의 알킬그룹을 나타내거나, 질소원자와 함께

를 나타낸다.Preferably, in general formula (III), R ₄ represents an alkyl group having 2 or 3 carbon atoms, or

Wherein R ₇ represents a hydrogen atom or a methyl group, X represents a hydrogen or halogen atom, and R ₅ and R ₆ represent an alkyl group having 2 to 5 carbon atoms, or together with a nitrogen atom

Indicates.

Examples of thiol carbamate of general formula (III) include S-ethyl N, N-hexamethylenethio carbamate (molinate), S-4-chlorobenzyl N, N-diethylthio carbamate (benthio carb), S-benzyl N-ethyl-N- (1,2-dimethylpropyl) thiocarbamate, and S- (1-methyl-1-phenethyl) -piperidine-1-carbothioate.

The above examples of formulas (II) and (III) and also the aforementioned compounds of formulas (IV) and (V) are already known (The Pesiticide Manual, 7th edition, 1983).

The weight ratios of the active ingredients in the active ingredient combinations according to the invention can be varied within a relatively wide range. For example, 0.01 to 15 parts by weight, preferably 0.1 to 10 parts by weight of active ingredient (2) can be used per part by weight of active ingredient (1).

The active ingredient combinations according to the invention can be used as herbicides, for example selective herbicides, pre-germination soil treatments or leaves and soil treatments.

Weed, in a broad sense, means all plants that grow in unwanted places.

The active ingredient combination according to the invention acts as a non-selective herbicide or as a selective herbicide depending on the concentration used.

The active ingredient combinations of the invention can be used, for example, in connection with the following plants.

Dicotyledonous weeds: Sinapis, Lepidium, Gallium, Stellaria, Kenopodium, Urtica, Senegio, Amaranthus Amaranthus, Potulaca, Xanthium, Ipomoea, Polygonum, Ambrosia, Cirsium, Sonchus, Rorippa Lamium, Veronica, Datura, Viola, Galeopsis, Papaver, Centaurea, Galinsoga, Rotala (Rotala), Lindernia, Videns, Doipatrium, Eclipta, Elatine, Gratiola, Lindernia , Ludwigia, Oenanthe, Ranunculus and Decinostema.

Monocotyledonous weeds: Echinochloa, Setaria, Panicum, Digitar-ia, Phleum, Poa, Festuca , Eleusine, Lolium, Bromus, Cyperus, Agropyron, Monochoria, Fimbristylis, Sagittaria , Eleocharis, Scirpus, paspalum, Inchaemum, Agrostis, Alopecurus, Cynodon, Alisma , Aneilema, Blyxa, Eriocaulon and potamogeton.

Dicotyledonous genus: Gossypium, Glycine, Beta, Doucus, Paseolus, Pisum, Solanum, Linum , Ipomoea, Vicia, nicotiana, Lycopersicon, Arachis, Brassica, Ractuca, Cucumis And Cucurbita.

Monocotyledonous crops: Oryza, Zea, Triticum, Herdeum, Avena, Secale, Sorghum, Sorghum, Panicum, Saccharum, Ananas, Asparagus, and Allium.

In particular, the active ingredient combinations according to the invention can be used in connection with the following weeds.

The active ingredient combination according to the invention can be used particularly effectively as a selective rice preparation.

The active ingredient combination according to the present invention is a perennial plantation, for example, plantation, ornamental water plant, orchard, vineyard, citrus plantation, nut plantation, banana plantation, coffee plantation, tea plantation, rubber plantation, oil palm plantation, cocoa plantation It can also be used to control weeds of soft fruit vegetarians and cultivated farms. The active ingredient combinations according to the invention can also be applied for the selective control of weeds of annual plant cultivation.

The active ingredient combinations according to the invention can be formulated in conventional forms such as liquids, emulsions, wetting powders, suspending agents, powders, solubilizing agents, granules, emulsifiable concentrates and microcapsules in polymeric materials.

These formulations can be manufactured by a well-known method. This process can be carried out by mixing the active ingredient with a surfactant, ie an electrodepositing agent, ie a liquid diluent and / or diluent, and optionally an emulsifier and / or dispersant and / or a bubble former.

In the case of using water as the electrodeposition agent, an organic solvent can be used as a cosolvent. Examples of liquid diluents include aromatic hydrocarbons such as xylene, toluene and alkylnaphthalene, chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzene, ethylene chloride and methylene chloride, aliphatic hydrocarbons such as cyclohexane and paraffins such as mineral oil. Fractions and mineral oils and vegetable oils)], alcohols such as butanol, glycol, and ethers and esters thereof, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone, strong polar solvents (such as : Dimethylformamide and dimethyl sulfoxide) and water.

Examples of solid carriers include ammonium salts, natural earth minerals (e.g. kaolin, clay, talc, white pressure, quartz, etherpulzite, montmorillonite and diatomaceous earth), and synthetic soil minerals (e.g. polymeric silicates, alumina, and silicates). ). Granular solid carriers are pulverized and fractionated rocks (eg calcite, marble, pumice, calcite and dolomite), synthetic particles of inorganic and organic materials, and small-scale organic materials (eg sawdust, coconut husk, corn and tobacco stalks). ) May be included.

Examples of emulsifiers and / or blowing agents include nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty acid alcohol ethers such as alkyl aryl polyglycol ethers, alkylsulfonates, alkylsulfonates, and aryl sulfonates. ], And hydrolysis products of albumin.

Lignin sulfite waste liquor and methyl cellulose are suitable as dispersants.

Tackifiers can also be used in the formulations (dust, granules, and emulsifiable concentrates). Examples of tackifiers include carboxymethylcellulose, natural and synthetic polymers such as gum arabic, polyvinyl alcohol and polyvinyl acetate, natural phospholipids such as cephalin and lecithin, and synthetic phospholipids. Mineral oils and vegetable oils may also be used as additives.

Moreover, a coloring agent can also be used. Examples of colorants include inorganic pigments such as iron oxide, titanium dioxide and Prussian blue, and organic dyes such as alizarin dyes, azo dyes or metal phthalocyanine dyes. Trace elements such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can also be listed as examples thereof. The regimen generally contains from 0.1 to 95% by weight, preferably from 0.5 to 90% by weight of the active ingredient combination. The active ingredient combinations according to the invention can be used as is or as a preparation for weed control. Tank mixing is also possible.

The active ingredient combinations according to the invention can be used as a mixture with other known active compounds commonly used for rice, such as fungicides, insecticides, plant growth regulators, plant nutrients, soil improvers and other herbicides.

Examples of other herbicides are N (alpha, alpha-dylbenzyl) -alpha-bromo-tert-butyl-acetamide, 4- (2,4-dichlorobenzoyl) -1,3-dimethylpyrazol-5-yl -P-toluenesulfonate, 2- [4- (2,4-diclobenzoyl) -1,3-dimethylpyrazol-5-yloxy] acetophenone, 2- [4- (2,4-dichloro- 3-methylbenzoyl) -1,3-dimethylpyrazol-5-yloxy] -4'-methylacetophenone, alpha- (2-naphthoxy) -propionanilide, 2,4-bis (ethylamino) -6 -Methylthio-1,3,5-triazine, 4- (4-chloro-0-tolyloxy) butyric acid, S-ethyl 4-chloro-2-methylphenoxythioacetate, P-nitrophenyl-2, 4,6-trichlorophenyl ether, 3-isopropyl- (1H) -2,1,3-benzothiadiazine-4- (3H) -one-2,2-dioxide, N-2-biphenylsul Ponyl N '-(4,6-dimethoxy-1,3,5-triazin-2-yl) urea, methyl 2-{[(4,6-dimethoxy-pyrimidin-2-yl) amino carbonyl ] Aminosulfonylmethyl} benzoate, and N-[(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -4- Brassica carbonyl may be mentioned 1-methyl-pyrazol-5-sulfonyl amide.

The active ingredient combinations can be used as such or as ready-to-use solutions or diluent preparations, such as emulsifiable concentrates, suspensions, dusts, wettable powders or granules. The active ingredient combinations can be applied by conventional methods such as watering, spraying, atomizing, dusting, or granule scattering.

The active ingredient combinations according to the invention can be applied before or after germination of plants.

The proportion of active ingredient applied can be varied within substantial ranges. For example, the amount of active ingredient applied is 0.05 to 2.0 kg / ha, preferably 0.1 to 1.5 kg / ha.

While the individual active ingredients are weak in terms of herbicidal activity, the combinations according to the invention exhibit very effective synergistic herbicidal effects against various weeds, far exceeding the simply expected effects from the active ingredient combinations.

Excellent effects of the active ingredient combinations according to the invention will be shown by the following examples. However, the present invention should not be limited thereby.

Example 1

Test for herbicidal efficacy:

Preparation of Active Ingredients

Solvent: Dimethylformamide 5 parts by weight

Emulsifier: Benzyloxypolyglycol ether 1 part by weight

The solvents and emulsifiers in the amounts mentioned can be mixed with 1 part by weight of active compound to give a preparation of the suitable active ingredient as an emulsifier concentrate. The amount of the formulation mentioned is diluted with water.

Examination procedure

Pots (25 × 20 × 9 cm) are padded with 1 / 2,000 acres of paddy soil, sowing seeds in barnyard glass and high alpine genus. After immersion, 100 seed seeds (variety: Nihonbare) are evenly seeded on the surface of the soil and the pot is prevented in the greenhouse. When the seedlings grow to the 1-leaf stage, the surface is covered with soil 2 cm deep. Once the blood grows in the 2.5 to 3.2 leaf stage, a premeasured amount of the formulation prepared above is applied to the water surface. After 3 weeks of chemical treatment, the extent of injury to rice and the extent of herbicidal effect on blood are evaluated in comparison with the non-treated portions, respectively. Repeat the test twice.

The synergistic effect is assessed according to Colby's method of evaluation (Weeds, 15, 1967, pages 20-22).

According to Colby, the value of the expected effect of mixing two chemicals is represented by the following equation:

Wherein X represents control rate by herbicide A at dose pg / ha, Y represents control rate by herbicide B at dose qg / ha, and E represents herbicide A and dose qg / ha at dose pg / ha It is the anticipation rate expected when the herbicide B is mixed and used.

If the actual control rate is greater than E, the formulation of the preparation appears to have a synergistic effect. Since the actual control rate of the composition of the present invention is much larger than E, the composition of the present invention has a significant synergistic effect.

Claims (5)

(1) O-ethyl S, S-diphenyl phosphphoto dithioate of formula (I) and (2) (a) bowloacetamide of formula (II), (b) thiol cover of formula (III) Mate, (c) 1- (α, α-dimethylbenzyl) -3- (4-methylphenyl) of urea (IV) (urea and (d) S-2-methylpiperidinocarbonylmethyl of urea (V) A herbicide composition characterized in that it contains one or more structured active ingredient combinations of herbicidally active ingredients selected from the class consisting of O, O-dipropylphosphorodithioates.

Wherein R ₁ and R ₂ each represent an alkyl group, R ₃ represents an alkoxyalkyl group, R ₄ represents an alkyl group, or

Wherein R ₇ represents a hydrogen atom or an alkyl group and X represents a hydrogen or halogen atom, and R ₅ and R ₆ represent an alkyl group or together with a nitrogen atom

Indicates. 2. The weight ratio of (1) O-ethyl S, S-diphenyl phosphorodithioate to active ingredient (2) in the active ingredient combination is 1: 0.0.1 to 1: 15. Herbicide composition. A method of controlling weeds, characterized by applying the active ingredient combinations according to claim 1 to weeds and / or their habitats. Use of the active ingredient combination according to claim 1 for weed control. A method for preparing a herbicide composition, characterized in that the active ingredient combination according to claim 1 is mixed with a weighting agent and / or a surfactant.