DE2844811A1 - CARBAMINE ACID PHENYL ESTER, METHOD FOR PRODUCING THESE COMPOUNDS AND THIS CONTAINING HERBICIDE AGENT - Google Patents

Description

The invention relates to new phenyl carbamates, processes for the preparation of these compounds and a herbicidal agent containing at least one of these compounds.

Herbicidal 3- (carbamoyloxy) anilides are already known (BE-PS 686 239).

The object of the present invention is to create new active ingredients with superior herbicidal properties.

According to the invention, this object is achieved by an agent which is characterized in that it contains at least one compound of the general formula contains, in which R [deep] 1 C [deep] 1-C [deep] 2-alkoxy-C [deep] 1-C [deep] 2-alkyl, di-C [deep] 1-C [deep] 2 -Alkoxy-C [deep] 1-C [deep] 2-alkyl,

Cyan-C [deep] 1-C [deep] 2-alkyl, halogen-C [deep] 1-C [deep] 2-alkyl, Phenyl-C [deep] 1-C [deep] 2-alkyl, 1, 3-Dioxolan-2-yl-methyl, 2-methyl-1,3-dioxolan-4-yl-methyl, 2,2-dimethyl-1,3-dioxolan-4-yl-methyl or aminocarbonylmethyl, R [deep] 2 phenyl, phenyl substituted once or twice by halogen and / or methyl and / or methoxy and R [deep] 3 C [deep] 1-C [deep] 8-alkyl, C [deep] 2-C [deep] 8 -Alkenyl, cyclopropyl or trichloromethyl or R [deep] 1 is methyl or ethyl, R [deep] 2 is small alpha-cyano-benzyl or 1-cyano-2-phenylethyl and R [deep] 3 is ethyl.

The compounds according to the invention are surprisingly superior to the known anilides of the type described above in terms of herbicidal action and therefore enrich the prior art in this field.

The herbicidal action of these compounds extends against a large number of undesirable plant species, not against crop plants for which there is a pronounced spectrum of selectivities.

The following are examples of plant species that can be controlled very well:

Gramineae

Festuca sp., Alopecurus sp., Agrostis sp., Echinochloa, Setaria so., Sorghum sp., Poa sp., Lolium sp., Arrhenaterum sp.,

Phalaris sp., Phleum sp., Eleusine sp., Bromus sp., Hordeum sp. and other.

Cyperaceae

Cyperus sp. and other.

Liliaceae

Allium sp. and other.

Amaranthaceae

Amaranthus sp. and other.

Boraginaceae

Anchusa sp., Amsinckia sp., Myosotis sp. and other.

Caryophylaceae

Stellaria sp., Spergula sp., Cerastium sp. and other.

Chenopodiaceae

Chenopodium sp., Salsola kali, Atriplex sp., Kochia sp. and other.

Convolvulaceae

Ipomea sp. and other.

Compositae

Ambrosia sp., Lactuca sp., Senecio sp., Xanthium sp., Galinsoga sp., Centaurea sp., Matricaria sp., Helianthus sp., Chrysanthemum sp., Cichorium intybus and others.

Cruciferae

Brassica sp., Cheiranthus cheiri, Capsella sp., Thlaspi sp., Sinapis sp. and other.

Euphorbiaceae

Euphorbia.

Labiatae

Lamium sp., Galeopsis sp. and other.

Leguminosae

Medicago sp., Trifolium sp., Vicia sp., Cassia sp. and other.

Malvaceae

Abutilon theophrasti, Sida sp., Hibiscus sp., Anoda and others.

Papaveraceae

Papaver sp., Escholtzia and others.

Polygonaceae

Polygonum sp. and other.

Portulacaceae

Portulaca sp. and other.

Rubiaceae

Galium sp., Richardia sp. and other.

Ranunculaceae

Delphinium sp., Adonis sp. and other.

Scrophulariaceae

Linaria sp., Digitalis sp., Veronica sp. and other.

Solanaceae

Datura sp., Solanum sp., Physalis sp. and other.

Urticaceae

Urtica sp. and other.

Umbelliferae

Daucus carota and others.

To control seed weeds, application rates of 1 to 5 kg of active ingredient / ha are generally used.

The application against these plant species can be done pre-emergence or post-emergence. A particular advantage here is that the compounds according to the invention are specifically well tolerated in agricultural crops, in particular in cotton, potatoes, rice, soybeans and sugar beet.

The compounds according to the invention can be used either alone, in a mixture with one another or with other active ingredients. If necessary, other defoliant, crop protection or pest control agents can be added depending on the desired purpose.

If a broadening of the spectrum of activity is intended, other herbicides can also be added. For example, active ingredients from the group of triazines, aminotriazoles, anilides, diazines, uracils, aliphatic carboxylic acids and halocarboxylic acids, substituted benzoic acids and aryloxycarboxylic acids are suitable as herbicidally active mixing partners,

Hydrazides, amides, nitriles, esters of such carboxylic acids, carbamic acid and thiocarbamic acid esters, ureas, 2,3,6-trichlorobenzyloxypropanil, rhodanic agents and other additives.

Other additives also include, for example, non-phytotoxic additives which, with herbicides, can produce a synergistic increase in effectiveness, such as, inter alia, wetting agents, emulsifiers, solvents and oily additives.

The active ingredients according to the invention or their mixtures are expediently in the form of preparations, such as powders, scattering agents, granules, solutions, emulsions or suspensions, with the addition of liquid and / or solid carriers or diluents and optionally wetting agents, adhesives, emulsifiers and / or Dispersing aids, applied.

Suitable liquid carriers are, for example, water, aliphatic and aromatic hydrocarbons, such as benzene, toluene, xylene, cyclohexanone, isophorone, dimethyl sulfoxide, dimethylformamide, and mineral oil fractions.

Mineral earths, for example Tonsil, silica gel, talc, kaolin, attaclay, limestone, silicic acid, and vegetable products, for example flours, are suitable as solid carriers.

Surface-active substances that may be mentioned are, for example, calcium ligninsulphonate, polyoxyethylene alkylphenol ethers, naphthalenesulphonic acids and their salts, phenolsulphonic acids and their salts, formaldehyde condensates, fatty alcohol sulphates and substituted benzenesulphonic acids and their salts.

The proportion of the active ingredient (s) in the various preparations can vary within wide limits. For example, the agents contain about 10 to 80 percent by weight of active ingredients, about 90 to 20 percent by weight of liquid or solid carriers and optionally up to 20 percent by weight of surface-active substances.

The agents can be applied in the usual way, for example with water as the carrier in spray liquid quantities of about 100 to 1000 liters / ha. An application of the means in the so-called low-volume and ultra-low-volume process is just as possible as their application in the form of so-called microgranules.

The new compounds according to the invention can be prepared, for example, by

Compounds of the general formula

in the presence of organic bases, such as pyridine, or as alkali salts, for example sodium or potassium salt, either with

Compounds of the general formula reacted or with phosgene with the addition of inorganic or organic bases, for example sodium hydroxide or dimethylaniline, initially into the corresponding chloroformic acid esters of the general formula

transferred and this then with compounds of the general formula in the presence of bases, such as, for example, potassium carbonate, to react and the process products are isolated in a manner known per se, where R [deep] 1, R [deep] 2 and R [deep] 3 have the meaning given above.

Examples of suitable solvents for these reactions are ethyl acetate, acetonitrile, hexane, benzene, toluene, methylene chloride, carbon tetrachloride, tetrahydrofuran, dimethylformamide and other agents which are inert towards the reactants.

In all reactions, the reaction takes place at temperatures between 0 ° and the respective boiling point of the solvent.

The hydroxyanilides to be used as starting materials are obtained in a manner known per se by reacting the corresponding acid chlorides with m-aminophenol.

The following examples illustrate the preparation of the compounds according to the invention.

example 1

N- (2,2-diethoxyethyl) carbanilic acid [3- (2,2-dimethylvalerylamino) phenyl] ester

In a solution of 20.9 g (0.1 mol) of N- (2,2-diethoxyethyl) aniline in 50 ml of ethyl acetate, a solution of 28.3 g (0, 1 mol) of 3- (2,2-dimethylvalerylamino) phenyl chloroformate and at the same time a solution of 13.8 g (0.1 mol) of potassium carbonate in 70 ml of water were added dropwise. The mixture is stirred at room temperature for 30 minutes, then the organic phase is separated off, diluted with a little ethyl acetate, washed at 0 ° C. with dilute hydrochloric acid and sodium chloride solution, dried with magnesium sulfate and the solvent is distilled off under reduced pressure. The residue is recrystallized from ethyl acetate / pentane.

Yield: 36 g = 79% of theory

M.p .: 88-89 ° C

Example 2

N- (2-cyanoethyl) -3-methylcarbanilic acid [3- (trichloromethylcarbonylamino) phenyl] ester.

31.7 g of 3- (trichloromethylcarbonylamino) phenyl chloroformate, taken up in 100 ml of acetonitrile, are added dropwise to a solution of 16.0 g of N- (2-cyanoethyl) -3-methylaniline in 100 ml of acetonitrile. Then 12.1 g of N, N-dimethylaniline are added to the reaction mixture. The temperature rises to 46 ° C. The reaction mixture is heated to boiling for a further 10 minutes, cooled, stirred into 500 ml of ice water, and the precipitated substance is filtered off and recrystallized from isopropanol.

Yield: 31.5 g = 72% of theory

M.p .: 118 ° C

Example 3

N-Cyanmethylcarbanilic acid [3- (tert-butylcarbonylamino) phenyl] ester

25.57 g of chloroformic acid [3- (tert-butylcarbonylamino) phenyl] ester are added to a solution of 13.2 g of N-cyanomethylaniline in 150 ml of acetonitrile, then 12.1 g of N, N- Dimethylaniline was added dropwise and the mixture was heated to boiling for a further 15 minutes. After cooling, the batch is stirred into 1 l of ice water, the substance which separates out is suctioned off and, after drying, in vacuo recrystallized from a little acetonitrile.

Yield: 24.0 g = 68% of theory

M.p .: 173 ° C

Example 4

N- (2-cyanoethyl) carbanilic acid [3- (cyclopropylcarbonylamino) phenyl] ester

29.2 g of N- (2-cyanoethyl) aniline are dissolved in 200 ml of acetonitrile and then 23.97 g of chloroformic acid [3- (cyclopropylcarbonylamino) phenyl] ester are added with stirring, the temperature of the solution increasing to 35 ° C rises. After standing overnight, the solvent is distilled off in vacuo, the remaining oily residue is treated with water, the water is decanted off and the oil is crystallized using a 1: 1 mixture of isopropyl ether / isopropanol. The crystals are then recrystallized from isopropanol.

Yield: 16.59 g = 48% of theory

M.p .: 142 ° C

Example 5

N-Cyanomethyl-3-methylcarbanilic acid [3- (propionylamino) phenyl] ester

The potassium salt prepared from 64.4 g (0.39 mol) of propionic acid 3-hydroxyanilide is taken up in 300 ml of acetonitrile. When a solution of 81.4 g (0.39 mol) of N-cyanomethyl-N- (3-methylphenyl) carbamoyl chloride in 250 ml of acetonitrile is added dropwise with stirring in 5 minutes, the temperature rises from 28 to 44.degree Refluxed for minutes. After evaporation under reduced pressure, it is dissolved in ethyl acetate and water, washed at 0 ° C. with a little dilute sodium hydroxide solution, dried with magnesium sulfate and evaporated under reduced pressure. The initially oily residue crystallizes from ether.

Yield: 80.4 g = 61% of theory

M.p .: 97-99 ° C

The following compounds according to the invention can be prepared in an analogous manner.

Name of the connection. Physical constant

________________________________________________________________________________

N- (2,2-dimethoxyethyl) -carbanilic acid- m.p .: 71-73 ° C

[3- (propionylamino) phenyl] ester

N-cyanomethylcarbanilic acid- (3-pro- m.p .: 130 ° C

pionylaminophenyl) ester

N- (2-cyanoethyl) -3-methylcarbanilic acid- m.p .: 149-151 ° C

(3-propionylaminophenyl) ester

N-methoxyethylcarbanilic acid- [3-pro- m.p .: 71-72 ° C

pionylamino-phenyl] ester

N- (2-cyanoethyl) -4-methylcarbanilic acid- m.p .: 124-126 ° C

[3-propionylaminophenyl] ester

N- (2-cyanoethyl) -2-methylcarbanilic acid- m.p .: 120-122 ° C

(3-propionylaminophenyl) ester

N- (2-methoxyethyl) -3-methylcarbanil- M.p .: 82-84 ° C

acid (3-propionylaminophenyl) ester

N- (2,2-Dimethoxyethyl) -4-methylcarbanil- n [high] 20 [low] D: 1.5343

acid [3- (propionylamino) phenyl] -

ester

N- (2,2-dimethoxyethyl) -3-methylcarbanil- n [high] 20 [low] D: 1.5405

acid [3- (propionylamino) phenyl] -

ester

N- (2-Bromoethyl) -carbanilic acid- [3 m.p .: 86-87 ° C

(propionylamino) phenyl] ester

N- (2-Ethoxyethyl) -carbanilic acid- [3 m.p .: 83-84 ° C

(propionylamino) phenyl] ester

N- (2-cyanoethyl) -carbanilic acid- [3 m.p .: 126-128 ° C

(propionylamino) phenyl] ester

N- (2,2-dimethoxyethyl-2-methylcarbanil- M.p .: 105-107 ° C

acid [3- (propynylamino) phenyl] ester

Name of the connection. Physical constant

________________________________________________________________________________

N- (1-cyano-2-phenyl-ethyl) -N-methyl- m.p .: 104 ° C

carbamic acid [3- (propionylamino) -

phenyl] ester

N- (small alpha-cyanobenzyl) -N-ethyl-carbamine- M.p .: 76 ° C

acid [3- (propionylamino) phenyl] ester

N- (2-cyanoethyl) -3-methylcarbanil- M.p .: 122 ° C

acid [3- (tert-butylcarbonylamino) -

phenyl] ester

N- (2-cyanoethyl) -carbanilic acid- [3 m.p .: 118 ° C

(tert-butylcarbonylamino) phenyl] -

ester

N- (1,3-Dioxolan-2-yl-methyl) - m.p .: 98-99 ° C

carbanilic acid [3- (propionyl-

amino) phenyl] ester

3-methoxy-N- (2-methoxyethyl) - n [high] 20 [low] D: 1.5614

carbanilic acid [3- (propionyl-

amino) phenyl] ester

N- (4-methyl-1,3-dioxolan-2-yl- n [high] 20 [low] D: 1.5559

methyl) -carbanilic acid- [3- (propionyl-

amino) phenyl ester

N -cyanomethylcarbanilic acid- [3- (2.2- M.p .: 152-153 ° C

dimethylvalerylamino) phenyl] -

ester

N- (2-cyanoethyl) -carbanilic acid- [3 m.p .: 93-95 ° C

(2,2-dimethylvalerylamino) phenyl] -

ester

N- (2-cyanoethyl) -carbanilic acid- [3 m.p .: 136-137 ° C

(2-methylpropionylamino) phenyl] -

ester

N- (2-chloroethyl) -carbanilic acid- [3 m.p .: 101-102.5 ° C

(2,2-dimethylvalerylamino) phenyl] -

ester

N- (2-chloroethyl) -carbanilic acid- [3 m.p .: 107-109 ° C

(propionylamino) phenyl] ester

Name of the connection. Physical constant

________________________________________________________________________________

N- (2-phenylethyl) -carbanilic acid- [3 m.p .: 93-94 ° C

(propionylamino) phenyl] ester

N- (2-cyanoethyl) -carbanilic acid- [3 m.p .: 117-119 ° C

(crotonoylamino) phenyl] ester

N- (2-chloroethyl) -carbanilic acid- [3 m.p .: 131-133 ° C

(crotonoylamino) phenyl] ester

N- (2,2-dimethoxyethyl) -carbanilic acid- m.p .: 77-79 ° C

[3- (2,2-dimethylvalerylamino) -

phenyl] ester

N- (aminocarbonylmethyl) -carbanil- m.p .: 197 ° C

acid [3- (cyclopropylcarbonyl-

amino) phenyl] ester

N- (2-aminocarbonylethyl) -carbanil- m.p .: 166 ° C

acid [3- (cyclopropylcarbonylamino) -

phenyl] ester

N- (2-cyanoethyl) -3-methylcarbanil- m.p .: 175 ° C

acid [3- (cyclopropylcarbonylamino) -

phenyl] ester

N-cyanomethylcarbanilic acid- [3- (tri-m.p .: 102 ° C

chloromethylcarbonylamino) phenyl] -

ester

N- (2-cyanoethyl) -carbanilic acid- [3 m.p .: 137 ° C

(trichloromethylcarbonylamino) -

phenyl] ester

N- (2-methoxyethyl) -carbanilic acid- [3- n [high] 20 [low] D: 1.5509

(tert-butylcarbonylamino) phenyl] -

ester

N- (2-methoxyethyl) -3-methoxycarbanil- n [high] 20 [low] D: 1.5482

acid [3- (tert-butylcarbonylamino) -

phenyl] ester

N- (2-methoxyethyl) -carbanilic acid- [3 m.p .: 133 ° C

cyclopropylcarbonylamino) -phenyl] -

ester

Name of the connection. Physical constant

________________________________________________________________________________

N- (2-methoxyethyl) -carbanilic acid- [3- n [high] 20 [low] D: 1.5804

(trichloromethylcarbonylamino) phenyl] -

ester

N- (2-methoxyethyl) -3-methoxycarbanil- m.p .: 135 ° C

acid [3- (trichloromethylcarbonylamino) -

phenyl] ester

N- (2,2-dimethyl-1,3-dioxolan-4-yl- M.p .: 100-102 ° C

methyl) -carbanilic acid- 3- (2,2-dimethyl-

valerylamino) phenyl ester

The compounds according to the invention are colorless and odorless, crystalline or oily substances which are readily soluble in acetone, dimethylformamide, isophorone, cyclohexanone, tetrahydrofuran and dimethyl sulfoxide.

The production of some starting materials is explained in more detail below.

a) 2,2-Dimethylvaleric acid-3-hydroxyanilide

In a solution of 327 g (3 mol) of m-aminophenol in about 1 l of ethyl acetate, after addition of 400 ml of water and 76 g of magnesium oxide, 445 g (3 mol) of 2,2-dimethylvaleric acid chloride are added dropwise with stirring, the temperature being reduced by cooling at 10 - 20 ° C is maintained. The mixture is subsequently stirred at room temperature for 1 hour. 400 ml of concentrated hydrochloric acid are then added dropwise at 0-5 ° C. and the mixture is stirred for 10 minutes. The organic phase is then separated off, washed neutral with sodium chloride solution and dried with magnesium sulfate. Some of the ethyl acetate is distilled off and pentane is added to the residue, whereupon the reaction product crystallizes out.

Yield: 550 g = 83% of theory

M.p .: 155-156 ° C

The following are obtained analogously:

Propionic acid 3-hydroxyanilide m.p .: 183-185 ° C

2-methylpropionic acid 3-hydroxyanilide m.p .: 180 ° C

Crotonic acid 3-hydroxyanilide m.p .: 158-159 ° C

b) 3- (propionylamino) phenyl chloroformate

A solution of 177 ml of phosgene in 700 ml of ethyl acetate is mixed with 292 g (1.77 mol) of propionic acid 3-hydroxyanilide. A solution of 225 ml (1.77 mol) of N, N-dimethylaniline in 300 ml of ethyl acetate is then added dropwise with stirring and cooling to 10-15 ° C. The mixture is then subsequently stirred at 50 ° C. for 30 minutes. The solution, cooled to 10 ° C., is poured onto ice, stirred for about 10 minutes, the organic phase is separated off, washed with sodium chloride solution, dried with magnesium sulfate and evaporated under reduced pressure. The residue crystallizes on addition of 600 ml of pentane.

Yield: 327 g = 81% of theory

M.p .: 72-73 ° C

The following are obtained analogously:

Chloroformic acid 3- (2-methylpropionyl- m.p .: 69-71 ° c

amino) phenyl ester

Chloroformic acid 3- (crotonoylamino) - n [high] 20 [low] D: 1.5327

phenyl ester

Chloroformic acid 3- (2,2-dimethylvaleroyl- n [high] 20 [low] D: 1.5273

amino) phenyl ester

c) [3- (cyclopropylcarbonylamino) phenyl] chloroformate

100 ml of phosgene are condensed at -20 ° C., then taken up in 1 l of ethyl acetate and 177.2 g of 3-hydroxyanilide cyclopropanecarboxylic acid with a melting point of 184 ° C. are added at 0 ° C. while stirring. 121 g of N, N-dimethylaniline are then added dropwise to this reaction mixture with further cooling. The mixture is then stirred for a further hour at 40 ° C., the excess phosgene is expelled by a stream of nitrogen gas, the batch is cooled to room temperature and the ethyl acetate phase is extracted twice with 250 ml of ice water. After the organic phase has been separated off, it is dried with magnesium sulfate, the solvent is distilled off in vacuo and the residue obtained is crystallized by adding petroleum ether. 207 g (86% of theory) of the abovementioned substance with a melting point of 94 ° C. are obtained in this way.

The following are represented in an analogous way:

Chloroformic acid [3- (tert-butylcarbonyl- m.p .: 75 ° C

amino) phenyl] ester

Chloroformic acid [3- (trichloromethylcarbonyl- n [high] 20 [low] D: 1.5786

amino) phenyl] ester

The following examples serve to illustrate the possible uses and the superior herbicidal action of the compounds according to the invention.

Example 6

In the greenhouse, the compounds according to the invention listed in the table were sprayed on Solanum and Brassica as test plants using the post-emergence method at an application rate of 5 kg of active ingredient / ha, dissolved in 500 liters of water / ha.

The treatment result was rated 3 weeks after the treatment, with

0 = no effect and

4 = destruction of the plants

means. As can be seen from the table, destruction of the test plants was generally achieved.

Example 7

After emergence, the plants listed were treated in the greenhouse with the agents listed at an application rate of 3 kg active ingredient / ha. For this purpose, the agents were sprayed evenly over the plants. The evaluation was carried out by scoring, where 0 = "totally destroyed" and 10 = "not damaged". Here, 3 weeks after the treatment, the agents according to the invention showed a high selectivity with an excellent action against the weeds. The comparison agents did not show this selectivity.

Claims (50)

1. Phenyl carbamate of the general formula in the R [deep] 1 C [deep] 1-C [deep] 2-alkoxy-C [deep] 1-C [deep] 2-alkyl, di-C [deep] 1-C [deep] 2-alkoxy-C [deep] 1-C [deep] 2-alkyl, cyano-C [deep] 1-C [deep] 2-alkyl, halo-C [deep] 1-C [deep] 2-alkyl, phenyl-C [deep ] 1-C [deep] 2-alkyl, 1,3-dioxolan-2-yl-methyl, 2-methyl-1,3-dioxolan-4-yl-methyl, 2,2-dimethyl-1,3-dioxolane -4-yl-methyl or aminocarbonylmethyl, R [deep] 2 phenyl, phenyl substituted once or twice by halogen and / or methyl and / or methoxy and R [deep] 3 C [deep] 1-C [deep] 8-alkyl, C [deep] 2-C [deep] 8-alkenyl, cyclopropyl or trichloromethyl or R [deep] 1 methyl or ethyl, R [deep ] 2 small alpha-cyano-benzyl or 1-cyano-2-phenylethyl and R [deep] 3 denote ethyl. 2. N- (2,2-diethoxyethyl) carbanilic acid [3- (2,2-dimethylvalerylamino) phenyl] ester. 3. N- (2-cyanoethyl) -3-methylcarbanilic acid [3- (trichloromethylcarbonylamino) phenyl] ester. 4. N-Cyanmethylcarbanilic acid [3- (tert-butylcarbonylamino) phenyl] ester. 5. N- (2-cyanoethyl) carbanilic acid [3- (cyclopropylcarbonylamino) phenyl] ester. 6. N- (2,2-Dimethoxyethyl) carbanilic acid [3- (propionylamino) phenyl] ester. 7. N-Cyanmethylcarbanilic acid [3- (propionylamino) phenyl] ester. 8. N- (2-cyanoethyl) -3-methylcarbanilic acid [3- (propionylamino) phenyl] ester. 9. N- (2-methoxyethyl) carbanilic acid [3-propionylaminophenyl] ester. 10. N- (2-cyanoethyl) -4-methylcarbanilic acid [3- (propionylamino) phenyl] ester. 11. N- (2-cyanoethyl) -2-methylcarbanilic acid [3- (propionylamino) phenyl] ester. 12. N- (2-methoxyethyl) -3-methylcarbanilic acid [3- (propionylamino) phenyl] ester. 13. N- (2,2-Dimethoxyethyl) -4-methylcarbanilic acid [3- (propionylamino) phenyl] ester. 14. N- (2,2-Dimethoxyethyl) -3-methylcarbanilic acid [3- (propionylamino) phenyl] ester. 15. N- (2-Bromoethyl) carbanilic acid [3- (propionylamino) phenyl] ester. 16. N- (2-Ethoxyethyl) carbanilic acid [3- (propionylamino) phenyl] ester. 17. N- (2-cyanoethyl) carbanilic acid [3- (propionylamino) phenyl] ester. 18. N- (2,2-Dimethoxyethyl-2-methylcarbanilic acid [3- (propionylamino) phenyl] ester. 19. N-Cyanomethyl-3-methylcarbanilic acid [3- (propionylamino) phenyl] ester. 20. N- (1-Cyano-2-phenyl-ethyl) -N-methyl-carbamic acid [3- (propionylamino) phenyl] ester. 21. N- (small alpha-cyano-benyzl) -N-ethyl-carbamic acid [3- (propionylamino) phenyl] ester. 22. N- (1,3-Dioxolan-2-yl-methyl) -carbanilic acid- [3- (propionylamino) -phenyl] -ester. 23. 3-Methoxy-N- (2-methoxyethyl) carbanilic acid [3- (propionylamino) phenyl] ester. 24. N- (4-Methyl-1,3-dioxolan-2-yl-methyl) -carbanilic acid- [3- (propionylamino) -phenyl] -ester. 25. N-Cyanmethylcarbanilic acid [3- (2,2-dimethylvalerylamino) phenyl] ester. 26. N- (2-cyanoethyl) carbanilic acid [3- (2,2-dimethylvalerylamino) phenyl] ester. 27. N- (2-Cyanoethyl) carbanilic acid [3- (2-methylpropionylamino) phenyl] ester. 28. N- (2-chloroethyl) carbanilic acid [3- (2,2-dimethylvalerylamino) phenyl] ester. 29. N- (2-chloroethyl) carbanilic acid [3- (propionylamino) phenyl] ester. 30. N- (2-Phenylethyl) carbanilic acid [3- (propionylamino) phenyl] ester. 31. N- (2-cyanoethyl) carbanilic acid [3- (crotonoylamino) phenyl] ester. 32. N- (2-chloroethyl) carbanilic acid [3- (crotonoylamino) phenyl] ester. 33. N- (2,2-Dimethoxyethyl) carbanilic acid [3- (2,2-dimethylvalerylamino) phenyl] ester. 34. N- (Aminocarbonylmethyl) carbanilic acid [3- (cyclopropylcarbonylamino) phenyl] ester. 35. N- (2-aminocarbonylethyl) carbanilic acid [3- (cyclopropylcarbonylamino) phenyl] ester. 36. N- (2-Cyanoethyl) -3-methylcarbanilic acid [3- (cyclopropylcarbonylamino) phenyl] ester. 37. N- (2-cyanoethyl) -3-methylcarbanilic acid [3- (tert-butylcarbonylamino) phenyl] ester. 38. N- (2-cyanoethyl) carbanilic acid [3- (tert-butylcarbonylamino) phenyl] ester. 39. N-Cyanmethylcarbanilic acid [3- (trichloromethylcarbonylamino) phenyl] ester. 40. N- (2-cyanoethyl) carbanilic acid [3- (trichloromethylcarbonylamino) phenyl] ester. 41. N- (2,2-Dimethyl-1,3-dioxolan-4-yl-methyl) -carbanilic acid-3- (2,2-dimethylvalerylamino) -phenyl-ester. 42. N- (2-methoxyethyl) carbanilic acid [3- (tert-butylcarbonylamino) phenyl] ester. 43. N- (2-methoxyethyl) -3-methoxycarbanilic acid [3- (tert-butylcarbonylamino) phenyl] ester. 44. N- (2-Methoxyethyl) carbanilic acid [3- (cyclopropylcarbonylamino) phenyl] ester. 45. N- (2-methoxyethyl) carbanilic acid [3- (trichloromethylcarbonylamino) phenyl] ester. 46. N- (2-Methoxyethyl) -3-methoxycarbanilic acid [3- (trichloromethylcarbonylamino) phenyl] ester. 47. Process for the preparation of carbanilic acid [3- (alkylcarbamoylamino) phenyl] ester according to Claims 1 to 46, characterized in that compounds of the general formula in the presence of organic bases or as alkali salts either with compounds of the general formula implements or with Phosgene with the addition of inorganic or organic bases initially into the corresponding chloroformic acid esters of the general formula transferred and this then with compounds of the general formula reacts in the presence of bases and isolates the process products in a manner known per se, where R [deep] 1, R [deep] 2 and R [deep] 3 have the meaning given above. 48. Herbicidal agents, characterized by a content of at least one compound according to Claims 1 to 46. 49. Herbicidal composition according to claim 48 as a mixture with carriers and / or auxiliaries. 50. Herbicidal agent characterized by a content of carbamic acid phenyl esters produced by the method according to claim 47.