SE441091B - SUBSTITUTED DIFENYLETERS, HERBIEIDIC COMPOSITION INCLUDING THESE ASSOCIATIONS AND USE OF THE ASSOCIATIONS FOR CONTROL OF BREEDING GROWTH - Google Patents

Description

Examples of a compound within the scope of said formula which are preferred in accordance with the present invention are 1 '- (ethoxycarbonyl) ethyl 5- (2-chloro-4-trifluoromethylphenoxy) -2-bromobenzoate. From a generic point of view, it is preferred that the substituent R 1 in the above formula is alkyl containing up to 4 carbon atoms.

The present invention also relates to a herbicidal composition which contains from about 0.05 to 95% by weight based on the weight of the composition of a compound of the present invention represented by the foregoing formula. Such a composition also contains conventional additives for herbicidal compositions.

According to another aspect of the invention, there is provided the use of the compound of the above formula for controlling weed growth.

It should be noted that the stereo and optical isomers of compounds represented by the above formula are within the scope of the present invention.

The compounds of the invention are typically synthesized, for example, by reacting a desirably substituted benzoyl halide with an alcohol or a desirably substituted α-hydroxycarboxylic acid ester or by reacting an optionally substituted benzoic acid with a desirably substituted benzoyl halide. cultured u-halocarboxylic acid ester using known techniques.

The substituted benzoyl halides (or acids) and the substituted u-hydroxy (or α-halo) carboxylic acid esters can be obtained commercially or prepared by known techniques.

More specifically, a least stoichiometric amount of substituted benzoyl halide is added with stirring to the substituted α-hydroxycarboxylic acid, preferably in the presence of an acid acceptor, such as, for example, triethylamine, pyridine, N, N-dimethylaniline or the like. Since the reaction is typically exothermic, the substituted benzoyl halide is added in portions so that the temperature of the reaction mixture does not substantially exceed about ° C. When the compounds of the present invention are prepared by reacting a substituted benzoic acid with a u-halocarboxylic acid ester, the latter is preferably added to the former in the presence of an azo compound, for example 1,5-diazobicyclo (5.4.0) unec-5-one (DBU). In another synthetic procedure, the reaction may, if desired, be carried out in the presence of an inert solvent, for example, benzene, methylene chloride, chloroform, ethyl acetate, tetrahydrofuran or the like. After the completion of the addition of the substituted benzoyl halide to the α-hydroxycarboxylic acid ester (or the completion of the addition of the G-halocarboxylic acid ester to the substituted benzoic acid), the reaction mixture is heated to reflux and kept at reflux until the reaction proceeds to the desired degree.

The reaction mixture is then cooled to ambient temperature and is typically washed successively with dilute acid, dilute base and water and allowed to phase separate. Substituted diphenyl ether is recovered from the organic phase in a known manner, for example by evaporation, crystallization, vacuum drying or the like. If desired, the product, substituted in phenyl ether, can be further purified, for example, by recrystallization. The following Examples I-XI are illustrative of the synthesis of certain concretely substituted diphenyl ether compounds of the present invention.

EXAMPLE I 1 '- (ethoxycarbonyl) ethyl 5- (2-chloro-U-trifluoromethylphenoxy) -2-nitrobenzoate.

A 100 ml, 3-necked flask equipped with addition funnel, reflux condenser and magnetic stirrer was charged with 1.18 g (0.0l mol) of ethyl lactate and 0.79 g (0.0l mol) of pyridine in 30 ml of benzene. To the stirred solution was added, at room temperature (about 20 ° C), dropwise 3.79 g (0.0l mol) of 5- (2-chloro-H-trifluoromethylphenoxy) -2-nitrobenzyl chloride in 20 ml of benzene. An exothermic heating could be observed. After the addition was complete, the reaction mixture was heated to reflux and kept at reflux for 6 hours. The reaction mixture was then cooled, transferred to a separatory funnel and washed successively with 30 ml portions of 1-Normal hydrochloric acid, water, 1-Normal sodium hydroxide and water. The washed organic phase was dried over magnesium sulfate and concentrated on a rotary evaporator at 5500 to give 2.89 g of a light yellow oil identified as 1 '- (ethoxycarbonyl) ethyl 5- (2-chloro-H-trifluoromethylphenoxy) - 2-nitrobenzoate with: NMR (acetone, D6) 7.3 - 8.36 (complex multiplet, §H); , 35 áuwartett, m; 14.28 óuwartett, an), 1.62 δ (dlibblett, 3H); 1.25 Juzriplect, 521).

EXAMPLE II 1- (ethoxycarbonylmethyl) ethyl 5- (2-chloro-H-trifluoromethylphenoxy) -2-nitrobenzoate.

A 100 ml, 3-necked flask equipped with addition funnel, reflux condenser and magnetic stirrer was charged with 1.32 g (0.01 mol) of ethyl 3-hydroxybutyrate and 1.1 g (0.01 mol) of triethylamine in 30 ml of benzene. To the stirred solution was added dropwise at room temperature (about 2000) 3.69 g (0.01 mol) of 5- (2-chloro-U-trifluoromethylphenoxy) -2-nitrobenzoyl chloride in 20 ml of benzene. After the addition was complete, the reaction mixture was heated to reflux and kept at reflux for 6 hours. The reaction mixture was then cooled, transferred to a separatory funnel and washed f »WT '' BO 80056 06-2 was taken successively with 30 ml portions of 1-Normal hydrochloric acid, water, 1-Normal sodium hydroxide and water. The washed organic phase was washed over magnesium sulfate and concentrated on a rotary evaporator at 5500 to give 3.75 g of a brown oil identified as 1- (ethoxycarbonylmethyl) ethyl 5- (2-chloro-4-trifluoromethylphenoxy) -2 -nitrobenzoate by: NMR (acetone die 7.2 - 8; 5Å (complex multiplet, 6H); 56 (quartet, 1H); U, 155 (quartet, 2H); 2.755 (doubletL2H); 1.36 ( Tablet overlapping triplet, EXAMPLE 3 2'-Ethoxycarbonyl 5- (2-chloro-U-trifluoromethylphenoxy) -2-nitrobenzoate.

A 250 ml, 3-necked flask equipped with an addition funnel, reflux condenser and magnetic stirrer was charged with 2.70 g (0.05 mol) of 3-hydroxypropionic acid and 2.38 g (0.03 mol) of pyridine in 10 ml of methylene chloride. To the stirred solution was added at room temperature (about 20 ° C) 11.37 g (0.03 mol) of 5- (2-chloro-trifluoromethylphenoxy) -2-nitrobenzoyl chloride in 30 ml of methylene chloride. Exothermic heating could be observed. After the addition was complete, the reaction mixture was heated to reflux and kept at reflux for 22 hours. The reaction mixture was then cooled, transferred to a separatory funnel and washed twice with 100 ml portions of 1-Normal hydrochloric acid and once with 100 ml of water. In magnesium sulfate and concentrated in a rotary evaporator at 5500 to give 11.8 g of a viscous yellow oil identified as 2'-ethoxycarbonyl-5- (2-chloro-4-trifluoromethylphenoxy) - The washed organic phase was dried over -2 nitrobenzoate by: NMR (acetone d6) 7.2 - 8.8 M (complex multiplet, 6H); ü, 3¿ (triplet, 2H); 2.67 <5 (triplet, 2nd).

EXAMPLE IV 2 '- (Ethoxycarbonyl) ethyl 5- (2-chloro-N-trifluoromethylphenoxy) -2-nitrobenzoate A 100 ml, 3-necked flask equipped with addition funnel, reflux condenser and magnetic stirrer was charged with 20 ml of ethanol ... oon-. pvmw 71- »-» «Poon QUALITY 800560642 'and 5 ml of pyridine in 50 ml of methylene chloride. To the stirred solution was added dropwise at room temperature (about 2000) 2.26 g (0.005 mol) of 2 '- (chlorocarbonyl) ethyl 5- (2-chloro-N-trifluoromethylphenoxy) -2-nitrobenzoate in 15 ml of methylene chloride. After the addition was complete, the reaction mixture was heated to reflux and kept at reflux for ü2.5 hours. The reaction mixture was then cooled and concentrated on a rotary evaporator at 55 ° C.

The concentrated residue was taken up in 100 ml of methylene chloride, transferred to a separatory funnel and washed successively with 30 ml portions of 1-Normal hydrochloric acid, water, 7% aqueous ammonium hydroxide solution and water. The washed organic phase was dried over magnesium sulfate and concentrated on a rotary evaporator at 5500 to give 1.3 g of a yellow oil identified as 2 '- (ethoxycarbonyl) ethyl' -5- (2-chloro-U-trifluoromethylphenoxy) -2-nitrobenzoate with: NMR (chloroform) 7.0 - 8, 1 '(multiplet, 6H); H, 3β (multiplet, HH), 2.656 (triplet, 2H); 1.36 (triplet, EH).

EXAMPLE 1 '- (ethoxycarbonyl) methyl 5- (2-chloro-U-trifluoromethylphenoxy] -2- nitrobenzoate A 100 ml 3-necked flask equipped with addition funnel, reflux condenser and magnetic stirrer was charged with 1.25 g (0.0l2). mol) of ethyl glycolate and 0.80 g (0.0l mol) of pyridine in 35 ml of methylene chloride To the stirred solution was added dropwise at room temperature (about 20 ° C) 5.79 g (0.0l mol) of 5- (2 -chloro-4-trifluoromethyl-phenoxy) -2-nitrobenzoyl chloride in 20 ml of methylene chloride Exothermic heating could be observed After the addition was complete, the reaction mixture was heated to reflux and kept at reflux for 42.5 hours. and washed successively with 30 ml portions of 1-Normal hydrochloric acid, water, 7% aqueous ammonium hydroxide and water, the washed organic phase was dried over magnesium sulfate and concentrated in a rotary evaporator at 5500 to give 3.5 g of a yellow oil identified as l '- (ethoxycarbony l) methyl 5- (2-chloro-U-trifluoromethylphenoxy) -2-nitrobenzoate with: BO soossos-2 7.0 - 8, U 5 (multiplet, 6H); H, 826 (singlet, 2H); 4.255 (quartet, EH), 1.316 (triplet, an).

NMR (chloroform) EXAMPLE VI 1'-Ethoxycarbonyl-2'-oxopropyl-5- (2-chloro-H-trifluoromethylphenoxy) -2-nitrobenzoate A 100 ml 3-necked flask equipped with addition funnel, reflux condenser and magnetic stirrer was charged with 3.61 g (0.01 mol) - (2-chloro-4-trifluoromethylphenoxy) -2-nitrobenzoic acid and 1.53 g (0.01 mol) of 1,5-diazobicyclo (5, N, 0) undec-5 -en (DBU) in 50 ml To the stirred solution was added at room temperature Reaction-benzene. (about 20 ° C) 1.65 g (0.01 mol) of ethyl 2-chloroacetoacetate. the mixture was then heated to reflux and kept at reflux for 20.5 hours. The reaction mixture was then cooled, transferred to a separatory funnel and washed successively with 30 ml portions of 1-Normal hydrochloric acid, water, 7% aqueous ammonium hydroxide solution and water. The washed organic phase was dried over magnesium sulfate and concentrated on a rotary evaporator at 5500 to give 3.1 g of a brown oil identified as 1'-ethoxycarbonyl-2'-oxopropyl-5- (2-chloro-Ä). trifluoromethylphenoxy) -2-nitrobenzoate by: NMR (acetone, v16) 7.2 - 8.26 (multiplet, δ), δ (singlet, 1H1; lnzauuwartet, 214); 2.3 δ (singlet, 3H).

EXAMPLE VII 1 "- (ethoxycarbonyl) butyl 5- (2-chloro-H-trifluoromethylphenoxy) -2-nitrobenzoate A 100 ml 3-necked flask equipped with addition funnel, reflux condenser and magnetic stirrer was charged with 3.61 g (0, 1l mol) - (2-chloro-H-trifluoromethylphenoxy) -2-nitrobenzoic acid and 1.53 U (0.0l mol) DBU in 50 ml benzene. To the stirred solution, 2.19 g (0.01 mol) of ethyl 2-bromovalerate was added at room temperature.

The reaction mixture was then heated to reflux and kept at reflux for 22 hours. The reaction mixture was then cooled, transferred to a separatory funnel and washed successively with 30 ml portions of 1-Normal hydrochloric acid, water, 7% aqueous ammonium hydroxide solution and water. , __ ¿_ ._1 "ï". sooseoß-2 ten. The washed organic phase was dried over magnesium sulfate and concentrated on a rotary evaporator at 55 ° C to give 2.2 g of a brown oil identified as 1 '- (ethoxycarbonyl) butyl-5- (2-chloro-H- trifluoromethyl) -2-nitrobenzoate by: NMR (acetone then) 7.2 - 8.26 (multiplet, 6H); , 256 (triplet, 1H); H, 286 (quartet, 2H); 0.8 - 1.9s (multiplier, inn).

EXAMPLE VIII 1 '- (Phenoxycarbonyl) ethyl 5- (2-chloro-H-trifluoromethylphenoxy) -2-nitrobenzoate A 100 ml 3-necked flask equipped with addition funnel, reflux condenser and magnetic stirrer was charged with 5.61 g (0, 1l mol) - (2-chloro-Ä-trifluoromethylphenoxy) -2-nitrobenzoic acid and 1.53 g (0.0l mol) DBU in 50 ml benzene. To the stirred solution was added at room temperature (about 2000) 2.29 g (0.0l mol) of phenyl-2-bromoacetate. The reaction mixture was then heated to reflux and kept at reflux for 22.5 hours. The reaction mixture was then cooled, transferred to a separatory funnel and washed successively with 30 ml portions of 1-Norvat mal hydrochloric acid and sodium hydroxide and water. The washed organic phase was dried over magnesium sulfate and concentrated on a rotary evaporator at 55 ° C to give 2.58 g of a light green syrup-like liquid identified as 1 '- (phenoxycarbonyl) ethyl 5- (2-chloro-H-trifluoromethylphenoxy). ) -2-nitrobenzoate by: NMR (acetone, then 7.0 - 8.256 (multiplet, 11H); 55 (quartet, 1H); 1.686 (doublet, BH).

EXAMPLE IX 1 ”- (ethoxycarbonyl) propyl 5- (2-chloro-H-trifluoromethylphenoxy) -2- -nitrobenzoate A 100 ml 3-necked flask equipped with addition funnel, reflux condenser and magnetic stirrer was charged with 5.61 g (0 .01 mol) - (2-chloro-4-trifluoromethylphenoxy) -2-nitrobenzoic acid and 1.53 g (0.0l mol) of DBU in 35 ml of benzene. To the stirred solution was added dropwise at room temperature (about 20 ° C) 1.95 g (0.0l mol) of ethyl 2-bromobutyrate in 15 ml of benzene. Exothermic heating could be observed. After the addition was complete, the reaction mixture was heated to reflux and kept at reflux for 800 hours. The reaction mixture was then cooled, transferred to a separatory funnel and washed successively with 1 ml portions of 1-Normal hydrochloric acid, water, 7% aqueous ammonium hydroxide solution and water. The washed organic phase was dried over magnesium sulfate and concentrated on a rotary evaporator at 5500 to give 1.2 g of a light brown syrup-like liquid identified as 1 '- (ethoxycarbonyl) propyl-5- (2-chloro-H-trifluoromethylphenoxy) -2-nitrobenzoate by: NMR (acetone, dg) 7.2 - 8.26 (multiplet, 6H); , 156 (triplet, H); ü, 26 (quartet, 2H); 1.9 δ (quartet, 3H); 0.8 - 1.3 & (overlapping triplets, 6H).

EXAMPLE X 1'-Ethoxycarbonyl-3'-methylbutyl-5- (2-chloro-U-trifluoromethylphenoxy) -2-nitrobenzoate A 100 ml 5-necked flask equipped with addition funnel, reflux condenser and magnetic stirrer was charged with 1.60 g (0.01 mol) of ethyl u-hydroxyisocaptroate and 0.79 g (0.01 mol) of pyridine in H0 ml of methylene chloride. To the stirred solution was added dropwise at room temperature (about 2000) 3.79 g (0.0l mol) of 5- (2-chloro-H-trifluoromethylphenoxy) -2-nitrobenzoyl chloride in 10 ml of methylene chloride. Exothermic heating could be observed. After the addition was complete, the reaction mixture was heated to reflux and kept at reflux for H6.5 hours. The reaction mixture was then cooled, transferred to a separatory funnel and washed successively with 25 ml portions of 1-Normal hydrochloric acid, water, 5.51 aqueous ammonium hydroxide solution and water. The washed organic phase was dried over magnesium sulfate and concentrated on a rotary evaporator at 55 ° C to give 3.99 g of a viscous brown oil identified as 1'-ethoxycarbonyl-3'-methylbutyl-5- (2- chloro-4-trifluoromethylphenoxy) -2-nitrobenzoate with: NMR (acetone, dg) 7.2 - 8.36 (multiplet, 6H); , 26 (triplet, 1H); H, 26 (quartet, 2H), 1.86 (multiplet, 3H); 0.8 - 1.6 (multiplet, 9H). Ast sodseos-2 EXAMPLE XI _ 1 '- (ethoxycarbonyl) ethyl 5- (2-chloro-4-trifluoromethylphenoxy) -2- bromobenzoate _ A 100 ml 3-necked flask equipped with addition funnel, reflux condenser and magnetic stirrer was charged with 1.18 g (0.01 mol) of ethyl lactate and 0.79 g (0.01 mol) of pyridine in 50 ml of methylene chloride. To the stirred solution was added at room temperature (about 20 ° C) approximately 2.07 g (0.65 mol) of 5- (2-chloro-H-trifluoromethylphenoxy) -2-bromobenzoyl chloride in 10 ml of methylene chloride. Exothermic heating could be observed. After the addition was complete, the reaction mixture was heated to reflux and kept at reflux for 66 hours. The reaction mixture was then cooled, transferred to a separatory funnel and washed successively with 30 ml portions of 1-Normal hydrochloric acid, water, 7% aqueous ammonium hydroxide solution and water. The washed organic phase was dried over magnesium sulfate and concentrated on a rotary evaporator at 55 ° C to give 2.2 g of a viscous, yellow, syrup-like liquid identified as 1- (ethoxycarbonyl) -ethyl-5- (2-chloro). -H-trifluoromethylphenoxy) -2-bromobenzoate by: NMR (acetone, dg) 7.0 - 8.06 (multiplet, 6H); , 256 (quartet, 1H); 4.186 (aubbit fi, 3H); 1.686 (doublet, 3H); 1.186 (triplet, 6H).

Although the synthesis of the compounds of the present invention is illustrated in some detail in the above Examples I - XII, it should be noted that any compound within the scope of the present invention can be prepared by those skilled in the art in a simple manner by varying the choice of starting material. materials and to use illustrated techniques or any other appropriate techniques.

The compounds of the present invention have been found to be effective in regulating the growth of a variety of undesirable plants, i.e. weeds, if applied in a herbicidally effective amount to the growth medium before the emergence of the weeds The term "herbicidally effective amount" means the amount of compound or mixture of compounds required to damage or destroy the weeds so that after application it can not or after the appearance of the weeds in the growth medium.

Q 8005606-2 11 recover. The quantity of a particular compound or mixture of compounds applied to exhibit a satisfactory herbicidal effect can vary widely and depends on a variety of factors, such as, for example, hardiness of a particular weed species, weed distribution, climatic conditions. , soil conditions, method of application and the like. Typically, as little as 0.2 or less kilograms per hectare up to kilograms or more per hectare of compound or mixture of compounds may be required. The effectiveness of a particular compound against a particular weed species can, of course, be readily determined by relatively simple laboratory or field tests in a manner well known in the art. The compounds of the present invention may be used as such or in formulations with agronomically acceptable adjuvants, inert carriers, other herbicides or other commonly used agricultural compounds, for example pesticides, stabilizers, safenes, fertilizers and the like. The compounds of the present invention, whether in composition with other agronomically acceptable materials or not, are typically applied in the form of dusts, granules, wettable powders, solutions, suspensions, aerosols, emulsions, dispersions or the like in a manner well known in the art. . When provided with other typically agronomically acceptable materials, the amount of the compound or compounds of the present invention present in the formulation may vary widely, for example from about 0.05 to 95% by weight based on the weight of the formulation. Typical such formulations contain from about 5% to about 75% by weight of the compound or compounds of the present invention. The compounds of the present invention have been shown to be effective in controlling a variety of broadleaf and grassy weeds in application rates of 2 kg per hectare or less before or after the occurrence while not substantially damaging desirable crops, for example maize, wheat, rice and soybeans. Examples of weeds that can be effectively controlled by applying compounds of the present invention are wild mustard (Bassica kaber); yellow foxtail (Setaria glauca); crabgrass (Digitaria sanguinalis); coffeeweed (Sesbania spp.,); velvetleaf (Abutilon theophrasti); johnsongrass (Sorghum hale- 80056 06-2 12 ß pense); barnyardgrass (Echinochloa crusgal1i); jimsonweed (Datura stramonium); teaweed (Sida spinosa); tall morningglory (Roth); and similar.

Some of the compounds prepared according to Examples I-XII were tested for herbicidal activity against certain weed species under controlled laboratory conditions of light, temperature and humidity. Seeds of selected weeds were planted on plains. In pre-occurrence tests, the soil was treated with the selected compound immediately after sowing. In post-performance tests, the soil was treated with the selected compound after a two-week germination period. The compound was applied to the soil by spraying a solvent solution of the compound within the specified application range, the degree of weed growth was observed and the compound toxic effect was evaluated periodically after the application.

The following shows in tabular form the weed species (identified by trivial name) and the compound applied to the weed species (indicated by an "X" and identified with reference to the example in which it was produced). In all cases, the compound was applied before the application in an amount of 2 kg per hectare.

Ogräs Förening l I II IV V VI VII VIII IX X Teaweed XXXX Jimsonweed X _X XXXXXXX vila muscara 'lx _ xxxxxxx Yellow føx fi aii xxx X xxxx Large crabgrass XXXXXXXX Johnsongraas XXXXXXX Coffeeueed IXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXX D In the above experiments, it could be observed that all weeds were either killed or damaged beyond recovery within 21 - 22 days after the application of the special compound.

In the following table, the indicated compound after application was applied to specified weed species in an amount of 2 kg per hectare.

Weeds Association I I II III IV V VI VII VIII IX X Teaweed X X X X Jimsonweed X- X X X X X X X X X Wild mustard X X X X X X X X X X X yellow tox- taii X 'x x x x x x Large crab- grasu X * Johnsongrass X X X X Coffeeweed X. X X Velvetleaf X X X X X X. X X Wild oats X X X X Barnyard grass X X X Cockleburr X X X X In the above experiments it could be observed that all weeds were either killed or damaged beyond recovery within 21 - 22 days after the application of the special compound.

It has been observed that the compounds of the present invention in which the "A" substituent is other than nitro, for example halogen and especially bromine (as illustrated by the compound prepared according to Example XII) show somewhat better herbicidal activity in post-occurrence application than in brought before the performance in quantities _unÉs. for example at about 2 or less kg per hectare. according to the present invention, wherein the "A" substituent is nitro about 5 kg per hectare, the compounds ÉQQÉQUÄLITY 8005606-2 14 have generally been found to be effective when applied before or after the performance in amounts of 2 or less kg per hectare.

Although the invention has been described in detail in connection with illustrative embodiments thereof, it should be noted that the intention is not to limit the invention, as many variations may be made by those skilled in the art without departing from the scope of the invention as defined in the appended claims. . ~ __.'_ ___ i i ~ ifša.

Claims (5)

80056 06-2 15 PATENT REQUIREMENTS 1 A compound represented by the formula: 0 x 11 1 x c-o-n-c-o-R I /, Q A Y wherein: A is halogen, X is hydrogen or chlorine; Y is hydrogen or chlorine; R is alkylene or monosubstituted alkylene containing 1-3 carbon atoms, wherein the substituent is selected from alkyl, oxoalkyl or hydroxyalkyl containing 1-4 carbon atoms; and R 1 is hydrogen, alkyl containing 1-10 carbon atoms, or phenyl. A compound according to claim 1, wherein R 1 is alkyl containing up to 4 carbon atoms. A compound according to claim 1, which is 1 '- (ethoxycarbonyl) ethyl 5- (2-chloro-4-trifluoromethylphenoxy) -2-bromobenzoate. 4. A herbicidal composition, characterized in that it contains from about 0.05 to 95% by weight, by weight of the composition, of a compound represented by the formula: WEX conco-R1 OAY wherein: A is halogen, X is hydrogen or claws; Y is hydrogen or chlorine; R is alkylene or monosubstituted alkylene containing 1-3 carbon atoms, wherein the substituent is selected from alkyl, oxoalkyl or hydroxyalkyl containing 1-4 carbon atoms and ~ .._._._ ;. . --.._ .. \ _ '.: __ \ l- .; R1 is hydrogen, alkyl containing 1-10 carbon atoms, or phenyl2 addition in addition to conventional additives for herbicidal compositions. Use of the compound of the formula according to any one of claims 1-3: Ü W c-o-x-c-o _-n1 1/0 A Y wherein: A is halogen, X is hydrogen or chlorine; Y is hydrogen or chlorine; R is alkylene or monosubstituted alkylene containing 1-3 carbon atoms, wherein the substituent is selected from alkyl, oxoalkyl or hydroxyalkyl containing 1-4 carbon atoms; and R 1 is hydrogen, alkyl containing 1-10 carbon atoms, or phenyl for controlling weed growth.