HU201229B - Synergetic herbicide compositions containing heterocyclic sulfonyl-urea derivatives - Google Patents

Abstract

Synergistic herbicides contain 0.005-95wt.% heterocyclic-sulphonyl-carbamide derivs. of formula (1) and one at least of the following cpds.: 2-chloro-4-ethyl-amino -6-isopropyl-amino-1,3,5-triazine (atrazine), 2-chloro-4-(1-cyano -1-methyl-ethyl-amino) 6-ethyl-amino-1,3,5-triazine (cyanazine), alpha-chloro 2',6'-di:ethyl-N-methoxy -methyl-acetanilide (alachlor) or 2-chloro-N-(2-ethyl-6- methyl-phenyl)-N-(2-methoxy -1-methyl-ethyl)-acetamide

Description

The present invention relates to compositions having a synergistic effect, comprising as active ingredient a compound of formula (I) and one of the following compounds: 2-chloro-4-ethylamino-6-isopropylamino-13,5-triazine (common name: atrazine) ), 2-chloro-4- (1-cyano-1-methylethylamino) -6-ethylamine ol, 3,5-triazmt (common name: cyanazine), ct-chloro2 ', 6'- diethyl N-methoxymethylacetanilide (common name: alachlor) or 2-chloro-N- (2-ethyl-6-methylphenyl) -N- (2-methoxy-1-methylethyl) acetamide (Common name: metolachlor).

During many years of research and development, many herbicides have been put into practice, contributing to weed control and improving crop productivity in agriculture and horticulture. Even today, many excellent new herbicides are needed. There is a particular need in agriculture and horticulture to ensure that only special weeds can be controlled selectively at low doses without the compounds being phytotoxic to the crop and existing herbicides do not always meet this requirement.

A 2.08.977 / 1985. The compound of formula (I) disclosed in Japanese Patent Application Laid-Open Publication No. 6,011,900 has excellent herbicidal activity compared to known herbicides in the literature and is also very safe for crops such as wheat, maize, etc. Not only is it effective against annual weeds and broadleaf weeds, but it is also effective against perennial weeds and is therefore very valuable.

In addition, it has been known in the literature to act against atrazine, cyanazine, alachlor and metolachlor, annual herbaceous weeds, such as Echinochloa crus-galli, Green Muhar (Setaria Viridis), Pirosia (Digitaria sanguinalis), etc., and high doses ( Compound of Formula I against annual broadleaf weeds. Consequently, perennial and broadleaf weeds are resistant to these chemicals and are difficult to apply, so new herbicides have to be developed.

In the course of developing the present invention, studies have been conducted to enhance the herbicidal activity of the compound of formula (I) and it has been found that when the compound of formula (I) is combined with atrazine, cyanazine, alachlor or metolachlor but a synergistic herbicidal effect is created. This synergistic effect is very high and, using the composition of the invention, annual and perennial weeds can be completely eliminated at low doses without damaging the grain and therefore of great importance to the invention. By using the above mixture, it is possible to reduce the dose of atrazine, cyanazine, alachlor and metolachlor and thus increase the significance of the composition of the invention. The herbicidal composition according to the invention can be applied before or after emergence of the weeds, and therefore a very effective effect can be achieved by treating the soil and / or treating the soil and the plant. In addition to cereals, various crops can also be used for weed control in other fields of agriculture and horticulture, such as fields, fields and orchards, non-crop fields, examples of athletic fields, empty lands, wooded areas, railways, etc. and are very cost effective in the field of weed control. The composition of the invention will generally contain from 0.001 to 70 parts by weight of the compound of formula I together with atrazine, cyanazine, alachlor or metolachlor, and the weight ratio will be (1-50) :( 1000), although this ratio may vary depending on the relative activity of the respective components. In many cases, it may be advantageous if the amount of the compound of formula QI is lower than that of the herbicide, for example, the compound of formula I may be used in an amount of 0.001-0.5 parts by weight per part by weight of atrazine, cyanazine, alachlor or metolachlor. The dosage of the mixture will depend on a number of factors, such as the species of target plant, whose growth must be inhibited and will generally vary from 0.01 to 10 kg of active ingredient per hectare. One skilled in the art can easily determine the appropriate application rate without much experimentation.

The determination may be carried out according to a standard conventional test. The composition of the present invention is used in the form of customary solid or liquid carriers, preferably containing a surfactant.

In preparing the herbicidal composition of the present invention, the active ingredient is formulated with a suitable carrier such as a solid carrier such as clay, talc, bentonite, diatomaceous earth and the like. or a liquid carrier such as water, alcohols such as methanol or ethanol, or aromatic hydrocarbons such as benzene, toluene or xylene or chlorinated hydrocarbons such as ethers, ketones, esters such as ethyl acetate, or acid amides such as dimethylformamide . The composition may also contain an emulsifying agent, a wetting agent, a dispersing agent, a binder, a penetration aid, a spreading aid, a stabilizer, and the like. and the formulation may be an emulsifiable concentrate, a soluble concentrate, a wettable powder, granules, a powder, a suspension, a concentrate, and the like.

The synergistic action of the herbicidal mixture can be explained as follows. In many cases the herbicidal activity of the individual active substances is unsatisfactory. In such a case, if the herbicidal effect is obtained from a combination of two active ingredients, the effect is greater than the sum of the effects of the two components or the sum of the expected effects, this is called a synergistic effect. The degree of synergistic effect is calculated according to Colby (S. R. Calculating Synergistic and Antagonistic Response of Herbicide Combinations, "Weed", Vol. 15, pp. 20-22 / 1967) according to the following equation

E = a + β- (α.β / 100) a =% herbicidal inhibitory activity in kg / ha; β = herbicide B% at b kg / ha%;

E = expected effect of A + B herbicide at a dose of + b kg / ha.

That if the observed value exceeds the expected value

-2EN 201229 Β, the combination has a synergistic effect. The details of the invention are illustrated by the following examples, but are not intended to limit the amounts, the compounds and the formulation. The term part refers to parts by weight.

Formulation examples Example 1 A wettable powder is a compound of formula (I) 2.5 parts atrazine 47.5 parts Zeeklit A Part 42.0 (kaolin-type material, trademarked by Zeeklite Kogyo Co., Ltd.) Sorpol 5039 2.0 parts (alldl ether sulfate, trademarked by Toho Nagaku Co., Ltd.) soybean oil 2.0 parts Carplex (anti-allergy) 4 parts

(white coal, trademarked,

Shionogi Seiyaku Co. Ltd., product)

The above components are mixed and homogeneously powdered to form a wettable powder.

Example 2

Emulsifiable concentrate

Compound of Formula (I) lrész alachlor Part 43 xylene Part 35 dimethylformamide 15 parts soybean oil lrész Sorpol 2680 (a mixture of nonionic and anionic surfactants, trademarked by Toho Kagaku Co., Ltd.) 5 parts

The above components are mixed homogeneously and an emulsifiable concentrate is prepared.

Example 3 A wettable powder is a compound of formula (I) 5 parts cyanazine Part 55 Zeeklite A 32 parts (kaolin type trademarked by Zeeklite Kogyo Co., Ltd.) Soprol 5039 Part 2 (alkyl ether sulfate, trademarked) Toho Kagaku Co., Ltd.) soybean oil Part 2 Carplex (anti-caking agent) 4 parts (white coal, trademarked by Shionogi Seiyaku Co., Ltd.)

The above components are mixed and homogeneously pulverized to give a wettable powder.

Example 5

Emulsifiable concentrate

Compound of Formula (I) Part 1 meta 40 parts xylene Part 38 dimethylformamide 15 parts soybean oil Part 1 Sorpol 2680

(a mixture of nonionic surfactant and anionic surfactant, trademarked by Toho Kagaku Co., Ltd.)

The components can be emulsified by mixing

concentrate. Example 5 A composition of the formula (I) on rivers 2.0 parts atrazine 24.0 parts Agrisol S-710 10.0 parts (nonionic surfactant trademarked by Kao-Atlas Co., Ltd.) Runox 1000 C 0.5 parts (anionic surfactant trademarked by Toho Kagaku Co., Ltd.) 1% Rodopol Water 20.0 parts (thickener, trademark, Rohne Poulenc products) water 43.5 parts

The above components are mixed homogeneously to form a liquid formulation.

Example 6 Granules Compound of Formula I 0.1 Part Methachlor 1.0 Part Soybean Oil 1.0 Part Bentonite 53.0 Part Talc 44.9 Part

The above components are uniformly mixed and pulverized, then mixed and kneaded with the addition of a small amount of water with stirring and granulated with an extruder-type granulate paste and then dried to form a granulate.

Example 7

Liquid Preparation Compound of Formula I 1 part cyanazine 24 parts

Agrisol S-710 Part 10 (Non-ionic surfactant, trademarked by Kao-Atlas Co., Ltd.)

Runox 1000C 0.5 parts (anionic surfactant, trademarked by Toho Kagaku Co., Ltd)

1% Rodopol water 20 parts (thickener, branded by Rohne

Poulenc product) water 44.5 parts

The above components are homogeneously mixed to form a liquid formulation.

Example 8

Wettable powder

Compound of Formula (I) Part 1 alachlor Part 43 Calcium carbonate Part 36 Sorpol 5039 (alkyl ether sulfate, trademarked) Toho Kagaku Co., Ltd. product) 5 parts Soprol 5050 (sodium dioctylsulfosuccinate, trademarked Toho Kagaku Co., Ltd. product) 5 parts

-3HU 201229 Β

Carplcx (anti-caking agent, white carbon, brand name,

Shionogi Seiyaku Co., Ltd.

products)

The above components are mixed and homogeneously powdered to give a wettable powder.

Example 9

Wettable powder

Compound of Formula (I) 1 part 10 metolachlor 40 parts diatomaceous earth Part 56 Sorpol 5050 (Sodium dioctylsulfo- 10 parts -Succinate, trademarked Toho Kagaku Co., Ltd. product) 15 lignin sulfonate 5 parts

The above components are mixed and homogeneously powdered to form a wettable powder.

Test example

Herbicidal effect by soil treatment Place sterile soil in a plastic box of cm high, 30 cm wide and 10 cm deep. Seeds of Green foxtail, Setaria Viridis, Abutilon theophrastus and Amaranthus retroflexus (hairy pig) and Zea mays (maize) are planted in pots and seeded with Cyperus esculentus tubers. Spray 1 cm of soil. The next day, before the emergence of the weed seeds, the herbicide is sprayed evenly so that the active ingredients are contained in the prescribed amounts.

When spraying, the wettable powder, emulsifiable concentrate, liquid formulation prepared according to the above formulation examples is diluted with water and sprayed with a small sprayer. Four weeks after spraying, the fresh weights of the above-ground parts of the weeds were determined according to the following formula and expressed as a control ratio.

control ratio (%) = [l- (fresh mass of treated weeds / fresh weight of untreated weeds)] x 100

Table 1 shows the results, the application of the compound of formula I, atrazine, cyanazine and alachlor separately, and Table 2 illustrates the use of the mixture.

Table 1

Individual action of each herbicide

Compound agent The dose g / ha Z.M. S. V. Control rate (%) A.T. PRICE. C. E. Of formula (I) 2.5 0 14 16 13 34 compound 10 0 24 48 46 80 40 0 46 91 91 100 atrazine 125 0 48 11 46 0 500 0 67 69 100 12 cyanazine 125 0 36 23 59 0 500 0 79 69 100 12 alachlor 125 0 91 0 33 36 1000 0 100 24 68 78 metolachlor 250 0 100 0 27 44 1000 0 100 12 58 83

Abbreviations in the table refer to the following plants:

Z.M. = Zea mays (corn)

S. V. = Setaria viridis (green mohar)

A. T. = Abutilon theophrasti

PRICE. = Amaranthus retroflexus

C. E. = Cyperus esculentus

-4EN 201229 Β

II. spreadsheet

The herbicidal action of the mixture

Compounds Mixed Action-Control Ratio (%) Aqueous Substance Dose Z.M. S. V. A. T. PRICE. C. E. dilution

(G / ha) Vf ve Vf ve Vf ve Vf ve Vf ve gold Atrazine + 125 + 2.5 0 0 83 55 61 25 88 53 71 34 2500 + (I) image.v. 125 + 10 0 0 96 61 88 54 100 70 100 80 1250 125 + 40 0 0 99 72 100 92 00 95 100 100 625 500 + 2 ^ 0 0 100 71 100 74 100 100 85 42 500 500 + 10 0 0 100 75 100 84 100 100 100 82 250 500 + 40 0 0 100 82 100 97 100 100 100 100 125 Cyanazine + + Formula (I): 125 + 2.5 0 0 76 45 69 35 100 64 75 34 2500 125 + 10 0 0 85 51 89 60 100 78 100 80 1250 125 + 40 0 0 91 65 100 93 100 96 100 100 625 500 + 2.5 0 0 100 82 100 74 100 100 83 42 500 500 + 10 0 0 100 84 100 84 100 100 100 100 250 500 + 40 0 0 100 89 100 97 100 100 100 100 125 Alachlor + 250 + 2.5 0 0 100 92 48 16 79 42 95 58 1000 + Formula (I): 250 + 10 0 0 100 93 81 48 99 64 100 87 500 250 + 40 0 0 100 95 100 91 100 94 100 100 250 1000 + 2 ^ 0 0 100 100 71 36 100 72 100 85 250 1000 + 10 0 0 100 100 98 61 100 82 100 96 125 1000 + 40 0 0 100 100 100 93 100 97 100 100 62.5 Metolachlor + 250 + 2.5 0 0 100 100 50 16 77 36 98 64 1000 + (I) image 250 + 10 0 0 100 100 79 48 99 60 100 89 500 250 + 40 0 0 100 100 100 91 100 93 100 100 250 1000 + 2 ^ 0 0 100 100 61 26 100 63 100 89 250 1000 + 10 0 0 100 100 92 54 100 77 100 97 125 1000 + 40 0 0 100 100 100 92 100 96 100 100 62.5

In the table, Vf represents a value found and Ve represents a value calculated using a Colby formula.

It is apparent from the above results that the composition according to the invention not only shows the sum of the action of the known herbicide and the compound of formula (I) but also has a synergistic effect. Low-dose selective and total weed control.

Claims (6)

PATENT CLAIMS CLAIMS 1. A herbicidal composition comprising, as active ingredient, 0.001 to 70% by weight of a compound of formula (I) and at least one of 2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine, 2-chloro-4. - (1-cyano-1-methyl-ethylamino) -6-ethylamino-1,3,5-triazine, α-chloro-2 ', 6'-diethyl-N-methoxymethylacetanilide or 2-chloro-N - (2-ethyl-6-methylphenyl) -N- (2-methoxy-1-methylethyl) acetamide containing solid carriers, preferably natural minerals or liquid carriers, preferably water or an organic solvent and optionally surfactant, preferably anionic or together with nonionic surfactants and a weight ratio of the compound of formula (I) to the known kerbid (1:50): (1001000). The herbidd composition according to claim 1, characterized in that it contains 0.0025-0.32 parts by weight of a compound of the formula I per 1 part by weight of atrazine, 45 thianazine, alachlor or metalachlor. Composition according to claim 2, characterized in that it contains from 0.0025 to 0.32 parts by weight of the compound of the formula I per 1 part by weight of atrazine. A composition according to claim 2, characterized in that it contains 0.0025-0.32 parts by weight of a compound of formula I per 1 part by weight of cyanazine. Composition according to claim 2, characterized in that it is in the range of 0.0025 to 0.32 parts by weight of general formula (I) It contains 55 compounds per 1 part by weight of alachlor. 6. A composition according to claim 2, characterized in that it contains 0.0025-0.32 parts by weight of a compound of formula I containing 1 part by weight of methachloro.