CS199747B2 - Herbicide - Google Patents

Abstract

1. Acetanilides of the formula see diagramm : EP0001751,P10,F1 where R and R**1 each denotes alkyl of a maximum of 5 carbon atoms, R**2 denotes hydrogen, X denotes chlorine, and A denotes imidazole, or a salt thereof, which is attached via a ring nitrogen atom and may be mono- or polysubstituted by halogen or alkyl radicals or halogen and alkyl radicals each of a maximum of 4 carbon atoms.

Description

The present invention relates to a herbicidal composition which contains at least one new acetanilide as active ingredient. The invention further relates to a process for the production of these novel acetanilides, as well as to the use of these novel acetanilides to combat undesirable plant growth.

Haloacetanilides are already known which have herbicidal and growth-regulating properties. Of noteworthy economic importance is N-methoxymethyl-α-chloroacet-2,6-diethylanilide (cf. U.S. Patent 3,547,620). Furthermore, an active ingredient is also known which contains a 1,3-dioxolan-2-ylmethyl group (cf. DOS no.

405 510). The value of the known acetanilides lies in their herbicidal activity against numerous seed grass species. In addition, some dicotyledonous species can be combated with the above compound. However, there is a lack of active substances which, in addition to the herbicidal action against grasses, also have an improved action against broadleaf species and which, in particular, exhibit substantially increased tolerability by the crop plants which have been damaged by the known active substances.

It has now been found that the novel acetanilides of formula (I)

yCh-A

N ^X co-c ¹ R ^{1 2} (I) wherein

R is hydrogen or alkyl of 1 to 5 carbon atoms,

R ¹ is hydrogen or C 1 -C 5 alkyl,

A represents an imidazole residue which is bound via a ring nitrogen atom and which is optionally substituted by C1-C3 alkyl or once or twice by chlorine or bromine, or optionally substituted by one or twice chlorine and C1-C3 alkyl carbon, wherein A may also be imidazole salts, have a good herb ^; It has excellent selectivity in important crop plants.

According to the prior art, it was surprising that the acetanilides substituted with the imidazole residue according to the invention are characterized by this high degree of compatibility with crop plants.

The novel active compounds are suitable, according to the intended aim and dose, for the selective control of undesirable plants in certain crop plants comprising weeds and woody plant species, for controlling growth by suppressing plant growth or at a correspondingly high amount applied to total plant growth suppression.

At low doses, the compounds of the invention corresponding to formula I in which R and R @ ¹ are substituents at the 2- and 6-positions on the phenyl nucleus and are in each case C1 -C5 alkyl have particularly pronounced selectivity to useful plants.

For R, R1 and A in formula I, the following are possible:

For R, hydrogen, alkyl of 1 to 5 carbon atoms such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, normal and branched pentyl radicals;

for R 1, hydrogen, alkyl of 1 to 5 carbon atoms such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, normal and branched pentyl radicals;

for A via a ring nitrogen bonded imidazole residue, such as an imidazole residue,

2-methylimidazole, 4 (S) -chlorimidazole, 2-chloroimidazole, 4,5-dichloroimidazole, 2-methyl-1-4,5-dichloroimidazole, 2-ethyl-4,5-dichloroimidazole, 2-isopropyl-4,5-dichloroimidazole, 4- (5'-bromoimidazole, 4,5-dibromoimidazole, 2-methyl-4,5-dibromoimidazole, 2'-bromo-4,5-dichloroimidazole).

In addition, the residue A can also be bound in the form of a salt to one of the usual strong inorganic or organic acids, such as hydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid, tetrafluoroboric acid, fluorosulfonic acid, formic acid, halogenated carboxylic acid, e.g. trichloroacetic acid, alkanesulfonic acid, for example methanesulfonic acid, halogenated alkanesulfonic acid, for example trifluoromethanesulfonic acid, perfluorohexanesulfonic acid, arylsulfonic acid, for example dodecylbenzenesulfonic acid.

The novel acetanilides of the formula I can be prepared by the following processes:

Acethanilides of formula I are obtained by reacting 2-halo-N-halomethylacetanides of formula II with imidazole of formula H-A according to the following equation:

R, R ¹ and A are as defined above, while X is chlorine, bromine or iodine.

Some of the 2-halo-N-halomethyl acetyl anilides of the formula II are known from DAS 1 542 950, others can be prepared in an analogous manner by reaction of the corresponding azomethines with a haloacetyl halide.

The imidazole is expediently used in at least a molar amount, based on 2-halo-N1-halomethyl acetic acid.

The hydrogen halide liberated in the reaction is expediently bound by a suitable reagent, such as by means of organic bases, for example tertiamines or inorganic bases, for example alkali metal or alkaline earth metal carbonates or acidic carbonates. Hydrogen halide binding agents are added at least in a molar amount based on the imidazole used.

It is expedient to carry out the reaction in a solvent inert to the 2-halo-1-halogeno-methylacetanilides. Suitable solvents include: hydrocarbons such as petroleum ether, ligroin, cyclohexane, toluene, xylene; ethers such as diethyl ether, diisopropyl ether, dimethoxyethane, tetrahydro furan, dioxane, anisole; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, carbon tetrachloride, chlorobenzene; ketones such as acetone, methyl ethyl ketone; esters such as ethyl acetate, butyl acetate; sulfones such as dimethylsulfoxide, tetrahydrothio Mixtures of these solvents may also be used.

The reaction may be carried out at temperatures from 0 ° C and above. To accelerate the reaction, it is advantageous to work at the boiling point of the solvent or solvent mixture, but not above 200 ° C. Preferably, the reaction is carried out at temperatures ranging from 50 to 150 ^DEG C. After completion of the reaction, the reaction mixture is filtered, and the product, optionally after previous washing, is isolated from the filtrate by conventional means. When using a water-miscible solvent, it is generally preferred to remove the solvent after evaporation by filtration and replace it with a solvent which ·. not miscible with water. .

Furthermore, they may be. The new acetanilides of formula I can be prepared by reacting 2-halo-N-halomethylacetanilides of formula II with an imidazole salt of formula M®A © according to the following equation:

R

N 2 CO-CH 2 X (ID

»

R, R ¹ , A and X are as defined above,

M + means a silver ion, an alkali metal ion, or an equivalent of an alkaline earth metal ion.

The alkali metal, alkaline earth metal or silver imidazole derivatives of formula M + A - are prepared in a known manner by reacting imidazole of formula H-A and alkali metals or strong bases such as alkali metal hydroxide, alkali metal alkoxide, alkali metal amide or an alkali metal hydride or silver hydroxide, releasing hydrogen, alcohol or ammonia.

The reaction of the salts of M + N - with 2-halo-N-halomethyl acetanilides of the formula II is preferably carried out in polar, aprotic solvents such as nitriles such as acetonitrile, amides such as dimethylformamide, polyethers such as diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, sulfones , for example tetrahydrothiophene-1,1-dioxide, sulfoxides for example dimethylsulfoxide, ketones such as acetone, methyl ethyl ketone, dlisopropyl ketone, at temperatures between -30 ° C to + 50 ° C, preferably at room temperature.

The starting materials are expediently used in an equimolar ratio. The reaction products are isolated in the customary manner, optionally after separation of the formed inorganic salt M + X 'and optionally after washing of the polar, aprotic solvent with a solvent which is not miscible with water.

The salts of the acetanilides of the formula I can be prepared in a manner known per se from acetanilides of the formula I which can be prepared according to any of the processes described above by adding at least a molar amount of a strong inorganic or organic acid such as hydrochloric acid, hydrobromic acid, nitric acid. sulfuric acid, tetrafluoroboric acid, fluorine, sulfonic acid, formic acid, halogenated carboxylic acids, e.g. trichloroacetic acids, alkanesulfonic acids, e.g. methanesulfonic acids, halogenated alkanesulfonic acids, e.g. trifluoromethanesulfonic acids, perfluorohexanesulfonic acids, arylsulfonic acids, e.g. dodecylbenzenes.

The following example illustrates the production of new acetanilides and their salts. The correlation between parts by weight and parts by volume in this example is as kg per liter.

He did

30.2 parts by weight of 2-methyl-4,5-dichloroimidazole were dissolved in 35.0 parts by weight of a 30% methanolic sodium methoxide solution with the addition of 60 parts by volume of methanol and the solution was concentrated to dryness in vacuo at 30 ° C. The crystalline residue is then suspended in 200 parts by volume of absolute acetonitrile. With stirring at 10 ° C was added portionwise 49.2 parts by weight of ^2-chloro-2 ', 6 ^{<-dimethyl-N-chlormethylacetanilidu} -a reaction mixture was stirred for 16 hours at room temperature. After evaporation of the solvent in vacuo, the residue was partitioned between chloroform and water. After washing three times with water, drying and recrystallizing from toluene, 50.0 parts by weight of 2-chloro-4-dimethyl-N- (2-methyl-4,5,5-chloroimidazol-1-ylmethyl) acetanilide, m.p. 170 DEG, are isolated from the chloroform phase. C (Compound No. 8).

Accordingly, the following compounds are obtained:

R / С ^ А

C. R R1 AND melting point (CC) 1 2-СНз 6-СНз B N 1 127 2 2-СНз 6-С2Н5 106 3 2-СНз 6-СНз ен ₃ гг 1 116 4 2-СНз 6-СНз £ k and n ^ ci 1 95 5 '2-N 6-С2Н5 К ^ N N N 1 ^{C C C C C C C} C 88 6 2-C2H5 6-С2Н5 104 7 2-СНз 6-СНз 170 8 2-СНз 6-С2Н5 Whose. ecH ^ ct 165 9 2-СНз 6-СНз JCL Jtl W ^ CC 114 10 2-СНз 6-С2Н5 XI ^C Z ^H 5 functions. 100 ALIGN! 11 2-СНз 6-СН5 ‘-С ^ Су '^ - сг 161 12 2-СНз 6-С2Н5 . / С1 • лх ^Ь -С, Н ^ Ы ^ С2 112

The application of the active compounds according to the invention is carried out, for example, in the form of directly sprayable solutions, powders, suspensions, as well as high-percentage aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, scatters, granulates by spraying, fogging, dusting, sprinkling. watering. The use forms depend entirely on the intended use. In any case, they are intended to ensure the finest possible distribution of the active compounds according to the invention.

For the preparation of directly sprayable solutions, emulsions, pastes and oil dispersions, suitable fractions of medium to high boiling mineral oil, such as kerosene or diesel engine oil, tar oils, etc., oils of vegetable or animal origin, aliphatic , cyclic and aromatic hydrocarbons such as benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or derivatives thereof such as methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexane, chlorobenzene, iSoporone etc., strongly polar solvents, for example dimethylformamide, dimethylsulfoxide, N-methylpyrrolidone, water, etc.

Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders, oil dispersions by adding water. For the preparation of emulsions, pastes, or oil dispersions, the substances as such or dissolved in an oil or solvent may be homogenized with wetting agents, adhesives, dispersing or emulsifying agents in water. Concentrates consisting of the active ingredient, wetting agent, adhesive, dispersing or emulsifying agent and, optionally, solvent or oil can also be prepared, which concentrates are suitable for dilution with water.

Among the surfactants there may be mentioned: alkali metal, alkaline earth metal ligninsulfonic acid salts, ammonium salts, naphthalenesulfonic acid, phenolsulfonic acids, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, alkali metal dibutylnaphthalenesulfonic acid salts and alkaline earth metal salts, lauryl ether sulfates, sulfated , salts of fatty acids with alkali metals and alkaline earth metals, salts of sulfated hexadecanols, heptadecanols, octadecanols, salts of sulfated glycol ethers with fatty alcohols, condensation products of sulfonated naphthalene and derivatives of naphthalene with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol, polyoxyethylenoctylphenol ethers, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, condensation products of fatty alcohols Ethylated oxides, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin, sulfite waste liquors and methylcellulose.

Powder formulations, dusts and dusts can be prepared by mixing or grinding the active ingredients with a solid carrier.

Granules, for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers. Solid carriers are, for example, mineral clays such as silica gel, silicas, silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomite, calcium sulfate and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and plant products such as cereal meal, tree bark meal, wood meal and nut shell meal, powdered cellulose and other solid carriers.

The compositions contain between 0.1 and 95% by weight of active compounds, preferably between 0.5 and 50% by weight.

The novel herbicidally active anilides of the invention can be mixed and co-administered with numerous representatives of other classes of herbicidal or growth-regulating active ingredients. For example, diazines, benzothiadiazinones, 2,6-dinrtroanilines, N-phenylcarbamates, biscarbamates, thiolcarbamates, halocarboxylic acids, triazines, amides, ureas, diphenyl ethers, trradinones, uracils, benzofuran derivatives and others are suitable components of the mixture. Such combinations serve to broaden the spectrum of action and sometimes achieve synergistic effects. The following is an example of a number of active substances which, together with the novel compounds, provide mixtures for various application areas

NH2

NH2

NH2

CH3 of —N \

СНз —NHCHs

CHs

Z —N \

CH3

0CH3

ОСНз

NH2

R2

Cl

Br

Cl

Cl

Cl

Cl

Cl

OCH3

ОСНз

Br

R Rl R ² R ³ H I-C3H7 H H or a salt thereof H 1-C3H7 H Or a salt thereof —CH2 — ОСНз I-C3H7 H H

or a salt thereof

R NO _a

R

R1 R2 R2 ³

R ⁴

H F3C Η С2Н5 С4Н9 H F3C Η П-СЗН7 П-СЗН7 H F3C Η - СН2 — СН2С1 П-СЗН7 H SO2NH2 Η П-СЗН7 П-СЗН7 H F3C Η П-СЗН7 <] НзС НзС Η Η —СН [СгН5) 2 H F3C ΝΗ2 П-СЗН7 п-СзН7 H НзС Η П-СЗН7 П-С3Н7 R1 Ν — COR ² Ζ II R 0 R R1 R ²

H 1 -C 3 H 7

H - C (CH) - C = CH

H - CH2 --S = CH - CH2Cl

H 1 -C 3 H 7

H — СН (СНз) —CO — NH — C2 H5

H = N = C (CH 5) 2

R R ¹ R ² Q H CHs €> H C2H5 O СНз Ri \ N — C — S — R ² / II R 0 СНз R Rl R ² I-C3H7 1-C3H7 —СНг — CC1 = CCI2 I-C3H7 I-C 5 H 7 —CH2 — CC1 = CHCl П-С3Н7 П-С5Н7 C2H5 0- C2H5 C2H5 sek.C4H9 sek.C4H9 C2H5 П-С3Н7 П-С5Н7 П-СЗН7 1-C4H9 I-C4H9 C2H5 C2H5 C2H5 1-C3H7 _1- C ³ H ₇ ^CH ₃ / 7J-CSR V ³ H ₃ C ^CH 5 R

—CHž — СС1 = CHCI —CH2 — CC1 = 0C12

X

RCCOR ¹

CHs

Cl

Cl

Cl

X

Cl

Cl

H

Cl

H

H

Cl

H

H

H

H

Y

Cl

H

H

Cl

CH3

CH3

Cl

CH3

CH3

CHs

CH3

Rl

On

CH3

H or a salt thereof

On

CH3

C2H5

On

1-C3H7

СНз —CH2 — CH (CH3) 2

On

R R ¹ R ² R ³ X н terc.C4H9 Н С2Н5 SCH3 н 1-C3H7 Н 1-С3Н7 SCH3 н 1-C3H7 Н С2Н5 SCH3 н СНз Н I-C3H7 ЭСНз н 1-С3Н7 н С2Н5 Л С1 н н 1-С3Н7 С2Н5 н н -X С2Н5 С1 С1 н С2Н5 н СНз —С — CN С1 н I-C3H7 н СНз I-C3H7 С1 н I-C3H7 н 1-СзН7 ОСНз н СНз NC — С— AND н -4 С1 н 1 СНз С2Н5 н —СН (СНз) —СНг — ОСНз С1 н С2Н5 н —СН (СНз) - С - с С1

R \ N-C-R ²

Z II

R O

R R 1 R ²

СНз

СНз

C2H5 — СН (СбН5) 2

С2Н5

НС - С — С (СНз) 2— соон

R3

СНз

Η

СНз

СНз

ОСНз

ОСНз

ОСНз

.... ОСНз

СНз — СНг — СН (СНз] 2

СНз

L

R R ¹ R ² R3 NOa Cl Cl CF3 CF3 Cl H H H H COOH, or salts or esters of this compound —С — ОСНз II H CFs Cl II 0 —OC2H5 0 R Rl R ² terc.CíHo NHz SCH3 O* NH2 До СНз R R Rl R ² R ³ СНз H H СНз СНз Br Cl -CH-C2H5 t-C4H9 H СНз Cl Q H - (CH 2) 3 - 45

Rl

СНз

НзС \ N— /

НзС

НзС \ N—

OF

НзС — c

II o

C2H5

C2H5

C2H5

coocH,

COOCH, Cl

Cl СООЧ

Or salts, esters, or amides thereof

COOH

Cl

H

or salts, esters or amides thereof

or salts, esters or amides thereof

HO O \ ll

P — CH2 — NH — Nг — C — OH

HO O

H П-С3Н7 —CH2 — CH = СНг СНз

Na П-С3Н7 — СНг — CH = CH ₂ СНз

or salts thereof or salts or esters thereof

or a salt thereof

Furthermore, it is useful to apply the novel compounds according to the invention alone or in combination with other herbicides also in admixture with other plant protection agents, for example with pest control agents or phytopathogenic fungi or bacteria. Also important is the miscibility with mineral solution solutions which are used to suppress nutrient or trace element deficiencies.

The effect of various representatives of the compounds of the invention on the growth of undesirable and desirable plants as compared to known chemically similar active substances is demonstrated in the following experiments. A series of experiments were carried out in a greenhouse.

Plastic pots of 300 ml filled with clayey sand soil with about 1.5% humus as substrate served as plant pots. The seeds of the test plants as listed in Table 1 are sown separately by species. Immediately thereafter, the active substances are applied to the soil surface during the pre-emergence treatment. The active substances are suspended or emulsified in water as a dispersant and are applied by means of fine nozzles by spraying. After application, the containers are lightly sprinkled with water to facilitate. germination and growth while activating chemical agents. The containers are then covered with a transparent plastic film up to. emergence of plants. This covering causes even germination. test plants, if not affected by chemicals, and prevents evaporation. readily volatile substances.

The test plants are placed in a greenhouse, with thermophilic species preferably being placed in the warmer sections [25 ° C to 40 ° C] and those requiring a lower temperature are maintained at a temperature of 15 to 30 ° C. The experiment takes 4 to 6 weeks. After. during this time the plants are treated and their response to the individual treatments evaluated.

Table 2 contains the test substances, the doses at which they are applied in kg / ha of the active substance and the species of test plants. The evaluation is carried out on a scale from 0 to 100. In doing so. means 0 that no damage has occurred or. normal growth and 100 means that the plants did not grow or were completely destroyed at least in parts of the shoots above the ground.

Result:

Table 2 contains several numerical values for the biological characteristics of the novel compounds. Above all, these values show a significantly better compatibility. certain crop plants as compared to known active ingredients.

The table below shows the results it was. achieved. during pre-emergence treatment. Naturally, the new active substances can also be used for post-emergence investigations. Depending on the dose of the active compounds, complete plant death is achieved or, at lower application rates, only the inhibition of plant growth is achieved.

TABLE 1

List of tested plants Common foxtail (Alopecurus myosuroides) Sugar beet (Beta vulgaris) Hedgehog. Corn leg (Echinochloa crus galii) Soybean (Glycine max) Cotton (Gossypium hirsutum) Sorghum (So.rg.hum bicolor) Corn (Zeamays) (Setaria spp.) Og

H rL

I I • S and honor 4- *

N cn

CO O 2 o

Ui u

CO ад

Φ

Fh

I o

F-4 ω o ω φ> 4 and om cm gg

8

C8

O- o o -

IO CD o co [CM l tx o o γ — I

CD o

b *

LO CD

Selective herbicidal effect in pre-emergence application in greenhouse

ω Q Fh Φ Й CO> o 4- Φ Φ £ cc a

8888W8 8n

B> 8

CD ^S * O 03> * Bo i ⁴ £ O honors £ 4т4 03 and* t o J CjO CQ -Д at (J >

т-Ч Ρϋ

Φ

ooomrn o .oo rl HN © ooowooo oooomoon o co o_ 1П 8 ~ o Ln © o_ O ~ rH N ~ θ 'H ~ cT o rH C \ TN ~ rH Μ ¹ Щ

CD □ 8 CM N o

8J o ~ of

κΰ

4>

'СО cn Q Q

N r-I LO

CM = no damage

100 = dead plants or dead plants

Example 2 parts by weight of compound 1 are mixed with 10 parts by weight of N-methyl-.alpha.-pyrrolidone to give a solution which is suitable for application in the form of minimal drops.

Example Z parts by weight of compound 2 are dissolved in a mixture consisting of 80 parts by weight of xylene, 10 parts by weight of addition product, 8 to 10 moles of ethylene oxide with 1 mol of N-monoethanolamide oleic acid, 5 parts by weight of calcium dodecylbenzenesulfonic acid and 5 parts by weight. addition product of 40 moles of ethylene oxide with 1 mole of castor oil. By pouring this solution into 100,000 parts by weight of water and finely distributing it, an aqueous dispersion is obtained which contains 0.02% by weight of the active ingredient.

Example 4 parts by weight of Compound З are dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, З0 by weight of isobutanol, 20 parts by weight of an adduct of 7 moles of ethylene oxide with 1 mol of isooctylphenol and 10 parts by weight of an adduct castor oil. By pouring this solution into 100,000 parts by weight of water and finely distributing it there is obtained an aqueous dispersion containing 0.02% by weight of the active ingredient.

EXAMPLE 5 parts by weight of compound 1 are dissolved in a mixture consisting of 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction having a boiling point of 210 DEG to 280 DEG C. and 10 parts by weight of 40 mol of ethylene oxide with 1 mol of castor oil. . Pouring this solution into 100,000 parts by weight of water and finely distributing it gives an aqueous dispersion containing 0.02% by weight of the active ingredient.

EXAMPLE 6 parts by weight of active compound 2 are well mixed with 2 parts by weight of sodium diisobutylnaphthalene-sulfonic acid, 17 parts by weight of sodium ligninsulphonic acid from sulphite waste liquors and 60 parts by weight of powdered silica gel, and the mixture is ground in a mill. By finely distributing the mixture in 20,000 parts by weight of water, a spray suspension is obtained which contains 0.1% by weight of the active ingredient.

Example 7

Z parts by weight of Z compounds are intimately mixed with 97 parts by weight of finely dispersed kaolin. In this way, a dust is obtained which contains Z% by weight of the active ingredient.

Example 8

6 parts by weight of compound 4 are intimately mixed with a mixture of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil which has been sprayed onto the surface of the silica gel. In this way, an active substance preparation with good adhesion is obtained.

EXAMPLE 9 parts by weight of active ingredient 1 are intimately mixed with 10 parts by weight of the sodium salt of the condensation product of phenolsulfonic acid, urea and formaldehyde, 2 parts of silica gel and 48 parts of water. A stable aqueous dispersion is obtained. Dilution of 100,000 parts by weight of water gives an aqueous dispersion containing 0.04% by weight of active ingredient.

Example 10 parts of active ingredient 2 are intimately mixed with 2 parts of calcium dodecylbenzenesulfonic acid, 8 parts of polyglycol ether of fatty alcohol, 2 parts of sodium salt of phenol, urea and formaldehyde condensation product and 68 parts of paraffinic mineral oil. A stable oil dispersion is obtained.

Claims (1)

A herbicidal composition comprising a solid or liquid carrier and containing as active ingredient at least one acetanilide of the formula I N ^X CO-CM ₅ Ct ^R (I) wherein R is hydrogen or alkyl of 1 to 5 carbon atoms, ^R1 is hydrogen or alkyl of 1-5 carbon .atomy, A represents an imidazole residue which is bound via a ring nitrogen atom and which is optionally substituted by C1-C3 alkyl or once or twice by chlorine or bromine, or optionally substituted by one or two chlorine or C1-C3 alkyl wherein A may also be imidazole salts.