CS245798B2 - Herbicidal agent - Google Patents

Abstract

The present invention relates to herbicidal compositions which are characterized in that they contain as an active ingredient a compound of the general formula A CH, \ 1 3 R-0 -/OV-O-CH-COOR (A) in which R represents a group of the formula ci-/oV 2 Ri represents an alkyl group with 1 to 4 carbon atoms, in combination with a compound of the general formula B in which R2 represents a bromine or iodine atom and R3 represents an octyl group, or with a compound of the formula C

Description

(54) Herbicide

The subject of the present invention are herbicidal compositions which are characterized in that they contain as an active ingredient a compound of the general formula A

CH, \ ^{1 3}

R-0 -/OV- O-CH-CO OR (A) in which

R represents a group of the formula

^c i-/oV

R1 represents an alkyl group with 1 to 4 carbon atoms, in combination with a compound of general formula B

in which

R2 represents a bromine or iodine atom and R3 represents an octyl group, or with a compound of formula C

wherein the ratio of the component of formula (Aj, in which R represents a 6-chlorobenzoxazolyl group, to the component of formula (B) or (C) in the mixture ranges between 1:5 and 5:1 and the ratio of the component of formula (AJ, in which R represents a 2,4-dichlorophenyl group, to the component of formula (C) in the mixture ranges between 1:1 and 10:1, provided that when in formula (AJ, R represents a group of formula

c.^O>ct the combination of compounds of general formula (A) with compounds of general formula (Bj.

Since the compounds of general formula A have a center of asymmetry in the propionic acid moiety, said compounds may occur as pure stereoisomers or as mixtures of stereoisomers.

The compounds of the general formula A are particularly effective against monocotyledonous weeds, such as field dogweed (Alopecurus myosuroides) and wild oats (Avena fatua) (cf. DE-OS 2,640,730 and DE-OS 2,223,894).

The symbol R 1 especially represents an alkyl group having 1 to 2 carbon atoms.

Of the compounds of general formula A, the following compounds are of particular interest:

α-[4-(6-chlorobenzoxazolyloxy)phenoxy]propionic acid ethyl ester (Aij, α-[4-(2,4-dichlorophenoxy)phenoxy]propionic acid methyl ester (A2J (common name: Diclofop-methylj.

Of particular importance are compounds A1 and A2.

Of the compounds of general formula B, those compounds in which R3 represents an octyl group (common name "Bromoxynil-octyl ester J"), R2 represents a bromine atom (compound Bij) and Ioxynil-octyl ester in the case where R2 represents iodine (compound B2) are preferred. Both of these compounds are known from NL-OS 64 11 452 as agents for controlling weeds in cereals.

The compound of formula C, also referred to as (Ci), is described in Weed Research Organization, technical report No. 63.

Compounds of general formula B and C are characterized by good activity against dicotyledonous weeds such as Stellarla media and Chenopodium album.

The combination of compounds of general formula A with compounds of general formula B or C surprisingly exhibits synergistic effects.

The combinations of active ingredients according to the invention can be used to control undesirable plant species, such as field dogwood (Alopecurus myosuroides), wild oats (Avena fatua), bird's-foot trefoil (Stellaria media), white fescue (Chenopodium album), wild grass (Setaria viridis), Phalaris spec., wild cattail (Galium aparinej, chamomile (Matricaria), field mustard (Sinapis arvensej), Miosotis arvense in crops of useful plants, in particular in crops of cereals such as wheat, barley, preferably wheat.

The combinations according to the invention can be used either as mixtures prepared in a storage container (tankmix), whereby the individual active ingredients are only mixed with each other immediately before application, or as ready-made preparations. They can be obtained as ready-made preparations, for example, in the form of wettable powders, emulsifiable concentrates, solutions, dispersions, dusts or granules, and these preparations then optionally also contain the usual auxiliaries used in the production of such preparations, such as wetting agents, adhesives, emulsifiers, dispersants, solid or liquid inert substances, grinding aids and solvents.

Wettable powders are preparations that are uniformly dispersible in water, which may contain, in addition to the active substance, optional diluents or inert substances, wetting agents, for example polyoxyethylated alkylphenols, polyoxyethylated oleyl or stearyl amines, alkyl or alkylphenyl sulfonates and dispersants, for example sodium lignin sulfonic acid, sodium 2,2'-dlnaphthylmethane-6,6'-disulfonic acid, sodium dibutylnaphthalene sulfonic acid or sodium oleylmethyltaurine.

Emulsifiable concentrates can be prepared, for example, by dissolving the active ingredient in an organic solvent, for example in butanol, cyclohexanone, dimethylformamide, xylene, isophorone or also in higher boiling aromatic hydrocarbons with the addition of one or more emulsifiers. As emulsifiers, for example, calcium salts of alkylarylsulfonic acids, polyglycol esters of fatty acids, alkylarylpolyglycol ethers, polyglycol ethers of fatty alcohols, polyoxyethylated oleyl or stearylamines, condensation products of propylene oxide and ethylene oxide, alkylpolyethers, sorbitan esters of fatty acids, condensation products of alkylarylpropylene oxide and ethylene oxide and others can be used.

Dusts are obtained by grinding the active ingredient with finely dispersed solids, for example with talc, natural clays such as kaolin, bentonite, pyrophyllite or diatomite.

Granules can be produced either by spraying a solution of the active substance onto an adsorptive, granular inert material or by applying active substance concentrates with the aid of a binder, such as polyvinyl alcohol, sodium polyacrylic acid, methylhydroxyethyl cellulose or also mineral oils, onto the surfaces of carrier substances, such as sand, kaolinite or granular inert material. Suitable active preparations can also be produced in a manner customary for the production of granular fertilizers, optionally in a mixture with the fertilizer.

The synergistic active ingredient mixtures according to the invention, consisting of compounds of the general formulae A and B or C, can be prepared in the form of conventional preparations, in particular in the form of wettable powders, emulsifiable concentrates, solutions, dispersions, dusts or granules. The total active ingredient content in commercially available preparations is about 2 to 95% by weight, preferably 10 to 70% by weight, the remainder up to 100% by weight consisting of conventional auxiliaries used in the production of such preparations, such as adhesives, wetting agents, emulsifiers, dispersants, fillers, solvents and carriers.

In wettable powders, the total concentration of active ingredient ranges from about 10 to 80% by weight.

In emulsifiable concentrates, the total active ingredient content ranges from about 10 to 70% by weight.

In the case of granules, the concentration of active ingredient is about 2 to 10% by weight. Powder preparations contain about 5 to 20% by weight of the active ingredient mixture.

The present invention therefore also provides herbicidal compositions which contain from 2 to 95% by weight, preferably from 10 to 70% by weight, of an active ingredient combination of compounds of the general formulae

A and B or C, the remainder up to 100% by weight consisting of excipients commonly used in such compositions.

When applied, the concentrates are optionally diluted in the usual manner, for example wettable powders, emulsifiable concentrates and dispersions with water. Powder and granular preparations as well as sprayable solutions are generally not diluted with further inert substances before use. Depending on external conditions such as temperature, humidity, etc., the required application amount of the compositions according to the invention also varies. This amount can vary within wide limits and is generally between 0.2 and 10 kg/ha of active ingredient combination, preferably 0.3 to 2.0 kg/ha. .

The invention is further illustrated by the following examples:

Examples illustrating the composition and preparation of the products:

General regulation:

The active ingredient is dissolved at a temperature of 50 to 60 °C in the solvent mixture mentioned and then the second active ingredient is added, optionally in the form of a melt. The individual components of the emulsifier are added with good mixing and the mixture is allowed to cool. The emulsifiable concentrates obtained are slightly to slightly brown in color.

According to this method, the active ingredients and auxiliaries mentioned in Examples 1 to 12 are mixed with each other. The numerical data in the table correspond to parts by weight.

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Examples illustrating biological efficacy:

In the following examples illustrating biological efficacy, the test plants are grown in pots in a greenhouse. Applications of the water-diluted concentrates are made when the monocotyledons Aloiperarus myosuiraiideis, Avena fatua and wheat Triticum aestivum reach the 3-4 leaf stage and when the dicotyledons Stellaria media and Chenopodium album reach a height of 5-10 cm.

After 4 weeks, the effect (level of damage) is evaluated. In the tables, the level of effectiveness found exceeds the expected level of effect.

The expected degree of action is calculated according to the formula described by S. R. Colby, Calculating synergistic and antagonistic response of herbicide combinations (Weeds 15, pp. 20-22, 1967).

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E = expected damage caused by herbicides A + B at X + Y kg/ha applied rate.

If the actual damage is higher than the calculated one, then the effect of the combination is higher than the sum, i.e. there is a synergistic effect. In the following tables, the effect calculated according to the above formula is given in brackets when treating with combinations.

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Claims (2)

SUBJECT OF INVENTION 1. Herbicidal composition, characterized in that it contains as an active ingredient a compound of general formula A in which Rz represents a bromine or iodine atom and Ro represents an octyl group, or with a compound of formula C R-O-yu}- O-CH-COOfy NH? ci. 1 ci (A) in which f OCtyCOO c ₈ h ₁₇ R represents a group of the formula (O Cl wherein the relative ratio of the component of formula (A) in which R represents a 6-chlorobenzoxazolyl group to the component of formula (B) or (C) in the mixture is between 1:5 and 5:1 and the relative ratio of the component of formula (A) in which R represents a 2,4-dichlorophenyl group to the component of formula (C) in the mixture is between 1:1 and 10:1, provided that when in formula A the symbol R represents a group of the formula Cl R1 represents an alkyl group with 1 to 4 carbon atoms, in combination with a compound of general formula B Combinations of compounds of formula A with compounds of formula B are excluded. 2. The composition according to item 1, characterized in that it contains α-[4-(6-chlorobenzoxazolyloxy)phenoxy]propionic acid ethyl ester or α-[4-(2,4-dichlorophenoxy)phenoxy]propionic acid methyl ester as the compound of general formula A.