CS245798B2 - Herbicide agent - Google Patents

Abstract

It is an object of the present invention herbicidal compositions which are characterized by containing as active ingredient a compound of formula A CH, 1 3 R-O-O-O-CH-COOR (AND) in which R represents a group of formula ci- / oV 2 R 1 represents an alkyl group having 1 to 4 atoms carbon, in combination with a general compound of formula B in which R2 represents a bromine or iodine atom and R3 is octyl, or is a compound of formula C

Description

(54) Herbicidal product

SUMMARY OF THE INVENTION The present invention provides herbicidal compositions which comprise as an active ingredient a compound of formula (A)

CH, \ ¹³

R-O- / OV-O-CH-CO OR (A) wherein

R is a radical of formula

^c i / oV

R 1 represents a C 1 -C 4 alkyl group, in combination with a compound of 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 is 6-chlorobenzoxazolyl) to the component of formula (B) or (C) in the mixture is between 1: 5 and 5: 1, and is a 2,4-dichlorophenyl group, to a component of formula (C) in the mixture of between 1: 1 and 10: 1, provided that when in formula (AJ is R a group of formula

c. A combination of compounds of formula (A) with compounds of formula (Bj.

Since the compounds of formula (A) have an asymmetric center in the propionic acid moiety, they may exist as pure stereoisomers or as mixtures of stereoisomers.

In particular, the compounds of formula (A) are effective against monocotyledonous weeds such as foxtail (Alopecurus myosuroides) and deaf oats (Avena fatua) (cf. DE-OS 2 640 730 and DE-OS 2 223 894).

R @ 1 is especially C1 -C2 alkyl.

Of the compounds of 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-methyl).

Of particular interest are compounds A1 and A2.

Among the compounds of formula (B), those wherein R3 is octyl (common name) Bromoxynil-octyl ester J, R2 is bromo (compound Bij and Ioxynil-octyl ester when R2 is iodine (compound B2) are preferred). the 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. 1, p. 63.

The compounds of formula (B) and (C) exhibit good activity against dicotyledonous weeds, such as Stellarla media and Chenopodium album.

Surprisingly, the combination of compounds of formula A with compounds of formula B or C is characterized by synergistic effects.

The active compound combinations according to the invention can be used for controlling undesirable plant species such as field foxes (Alopecurus myosuroides), deaf oats (Avena fatuaJ, Stellaria media), goosefoot (Chenopodium album), venus (Setaria viridis), Phalaris spec., bedstraw (Galium aparinej, chamomile (Matricaria), mustard Sinapis arvensej, Miosotis arvense in crop plants, especially in cereal crops such as wheat, barley, preferably wheat.

The combinations according to the invention can be used either as mixtures prepared in a tank (tankmix), where the individual active ingredients are mixed with each other just before application, or as ready-to-use formulations, for example as wettable powders, emulsifiable concentrates, solutions, dispersions, dusts or granules and these optionally contain the customary auxiliaries used in the manufacture of such compositions as wetting agents, adhesives, emulsifiers, dispersants, solid or liquid inert substances, grinding aids and solvents.

Wettable powders are uniformly dispersible preparations which, in addition to the active ingredient, may contain, in addition to optional diluents or inert substances, wetting agents, for example polyoxyethylated alkylphenols, polyoxyethylated oleyl or stearylamines, alkyl or alkylphenylsulfonates and dispersants such as sodium ligninsulfonic acid, sodium 2,2'-dlnaphthylmethane-6,6'-disulfonic acid salt, dibutylnaphthalenesulfonic acid sodium salt, or oleylmethyltaurine sodium salt.

Emulsifiable concentrates may be prepared, for example, by dissolving the active ingredient in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene, isophorone, or else in higher boiling aromatic hydrocarbons, with the addition of one or more emulsifiers. As emulsifiers, for example, calcium salts of alkylarylsulphonic acids, polyglycol esters of fatty acids, alkylaryl polyglycol ethers, polyglycol ethers of fatty alcohols, polyoxyethylated oleyl or stearylamines, condensation products of propylene oxide and ethylene oxide, alkyl polyethers, sorbitan esters of fatty acids and propylene oxide and other ethylene condensation products.

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

Granules may be prepared either by spraying the active ingredient solution onto an adsorptive, granulated inert material or by applying the active ingredient concentrates with a binder such as polyvinyl alcohol, sodium polyacrylic acid, methylhydroxyethylcellulose or also mineral oils onto carrier surfaces such as sand, kaolinite or granulated inert material. Suitable active formulations may also be prepared in a manner customary for the production of fertilizer granules, optionally in admixture with a fertilizer.

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

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

For 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. The powder compositions contain about 5 to 20% by weight of the active compound mixture.

Accordingly, the present invention also relates to herbicidal compositions which contain from 2 to 95% by weight, preferably from 10 to 70% by weight, of an active compound combination of the compounds of the general formulas

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

For application, the concentrates are optionally diluted in conventional manner, for example, wettable powders, emulsifiable concentrates and dispersions with water. Powder and granular preparations as well as sprayable solutions are generally no longer diluted with other inert substances prior to use. Depending on the external conditions, such as temperature, humidity, etc., the required application rate of the compositions according to the invention also varies. This amount can be 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 following examples illustrate the invention:

Examples illustrating the composition and preparation of formulations:

General prescription:

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

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

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Examples illustrating biological activity:

In the following examples illustrating biological activity, test plants are grown in pots in a greenhouse. Application of water-diluted concentrates is performed when monocot plants of Aloiperarus myosuiraiideis, deaf oats (Avena fatua) and wheat (Triticum aestivum) reach the 3 to 4 leaf stage, and when the dicotyledonous plant Stellaria media and white goosefoot ( Chenopodium album) grow to a height of 5 to 10 cm.

After 4 weeks the effect (degree of damage) is assessed. In the tables, the degree of efficacy observed exceeds the expected level of efficacy.

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

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X = ° / o damage by herbicide A at k'g / ha of application rate,

Y =% herbicide B damage at Y kg / / ha applied rate,

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

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

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Claims (2)

OBJECT OF INVENTION What is claimed is: 1. A herbicidal composition comprising, as an active ingredient, a compound of formula (A) wherein: R2 represents a bromine or iodine atom and Ro represents an octyl group or with a compound of formula C R-O-yu} -O-CH-COOphs NH? whose. 1 ci (AND) in which f OCtyCOO c ₈ h ₁₇ R is a group of formula (O Cl wherein the ratio of the component of formula (A) in which R is 6-chlorobenzoxazolyl to the component of formula (B) or (C) in the mixture is between 1: 5 and 5: 1 and the ratio of component of formula (A) wherein R is a 2,4-dichlorophenyl group to a component of formula (C) in the mixture is between 1: 1 and 10: 1, provided that when in formula A R is a group of formula Cl R 1 represents a C 1 -C 4 alkyl group, in combination with a compound of formula B Cl excludes combinations of compounds of formula A with compounds of formula B. 2. A composition according to claim 1, wherein the compound of formula (A) is [alpha] - [4- (6-chlorobenzoxazolyloxy) phenoxy] propionic acid ethyl ester or N- [4- (2,4-dichlorophenoxy) phenoxy] propionic acid methyl ester. acid.