CS208137B2 - Herbicide means and method of making the active substances - Google Patents

Abstract

Novel carbamic acid phenyl esters have the formula I <IMAGE> (wherein R1 represents C1-C2 alkoxy- C1-C2-alkyl, di-C1-C2-alkoxy- C1-C2-alkoxy, CN-C1-C2-alkyl, Hal-C1-C2alkyl, HO-C1-C2-alkyl, phenyl-C1-C2-alkyl, 1,3-dioxolan-2- yl-methyl, 2-methyl-1,3-dioxolan-4- yl-methyl, 4-methyl-1,3-dioxolan-2- yl-methyl, 2,2-dimethyl-1,3-dioxolan- 4-yl-methyl or H2N-CO-C1-C2 alkyl, R2 represents phenyl optionally substituted by 1 or 2 substituents selected from Hal atoms and methyl and methoxy groups and R3 represents C1-C8-alkyl, C2-C8-alkenyl, cyclopropyl or Cl3C, or R1 represents methyl or ethyl, R2 represents alpha -CN- benzyl or 1-CN-2-phenylethyl and R3 represents ethyl). The compounds may be prepared from the appropriate 3-acylaminophenols or the chloroformates thereof. The novel compounds of the formula I have a herbicidal action and accordingly may be made up with suitable carriers into herbicidal preparations and may be used for protecting living plants and crop areas against weeds.

Description

The present invention relates to a herbicidal composition which, in admixture with carriers and / or excipients, contains novel carbamic acid phenyl esters and a process for the preparation thereof.

The herbicides 3- (carbamoyloxy) anilides are already known (BE Patent 686,239).

SUMMARY OF THE INVENTION It is an object of the present invention to provide novel active compounds having stronger herbicidal properties.

This object is achieved according to the invention by a composition comprising at least one phenyl carbamic acid ester of the formula I,

(I) in which R ^@ 1 С1 _{С-2--а1коху} С ^ ₂ -С -а1ку1, _{di-C 2} -C -alkoxy-C | -C ₂ -alkyl, cyano-C ₁ -C ₂ alkyl , halogen-C 1 -C ₂ -alkyl, phenyl-C ₁ -C ₂ -alkyl, 1,3 "dioxolan-2-yl-methyl, 2-methyl-1,3-dioxolan-4-yl-methyl, 2 , 2-dimethyl-1,3-dioxolan-4-ylmethyl or aminocarbonylmethyl,

R _{2 is} phenyl, phenyl substituted once or twice with halogen and / or methyl and / or mexy,

208137 2 ^R 3 ^c 1 ^c 8 ^а1к У1> ^C 2 ' ^C 8 cyclopropyl or trichloromethyl, or represent

R | methyl or ethyl,

Rg alpha-cyanbenzyl or 1-cyan-2-phenylethyl,

R 1 is ethyl.

Surprisingly, the compounds according to the invention are more effective than known anilides of the aforementioned kind in herbicidal activity and therefore enrich the state of the art in this field.

The herbicidal activity of these compounds relates to a large number of undesirable plant species, not to crop plants in which there is a significant selective spectrum.

The following are exemplified as very destructible plant species:

Gramineae

Festuca sp, Alopecurus sp, Agrostis sp., Echinochloa, Setaria so. (har), Sorghum sp. (sorghum), Poa sp. (meadow-grass), Lolium sp. (ryegrass), Arrhenaterum sp., Phalaris sp., Phleum sp., Eleusine sp., Bromus sp. (brome), Hordeum sp. (barley) and others;

Cyperaceae

Cyperus sp. (šáchor) and others;

Liliaceae

Allium sp. and other;

Amaranthaceae

Amranthus sp. (amaranth) and others;

Boraginaceae

Anchuaa sp., Amsinckia sp., Myosotis sp. and other;

Caryophylaceae

Stellaria sp. (chickweed), Spergula sp., Cerastium sp. and other;

Chenopodiaceae

Chenopodium sp. (goosefoot), Salsola káli, Atriplex sp. (Lebeda), Kochia sp. (kochia) and others;

Convolvulaceae

Ipomea sp. and other;

Compositae

Ambroia sp., Lactuca sp. (lettuce), Senecio sp. (nettle), Xanthium sp. (beet), Galinsoga sp. (centaurea), Centaurea sp., Matricaria sp. (camomile), Helianthus sp. (sunflower), Chrysanthemum sp. (daisy), Cichorium intybus and others;

Cruoiferae

Brassica sp. (brckev), Cheeranthcs cheeri, Capseeia sp., Thlaspi'sp. (penny), Sinapis sp. (mustard) and others;

& iphhobiaceae,

Eiphhobia;

Labbatae

Lamicrn sp. (rodent P, Galeopsis sp.) and others;

Legwninospe

Medicago sp. (alfalfa), Trifol CM sp. (clover), Vicia sp. (bean), Cassia sp. and other;

MaPvaceae

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

Papaveraceae

Papaver sp. (poppy), EscheOtzia and others;

Polygonaceae

Polygonům sp. and other;

Portclacaceae

Portclaca sp. and other;

Rubiaceae

Galiem sp. (bedstraw), Richardia sp. and other;'

Reanmculpcepe.

Delphiniim sp., Adonis sp. and other; ScrophuCariaceae

Linarip sp., Digitalis sp., Veronica sp. and other;

Solanacepe

Daticra sp., Solanccm sp. (eggplant), PsePis sp. and other;

Urticaceae

Urtika sp. (nettle) and others;

UmePPlferae

Daucus carota (carrots) and others.

As a rule, 1 to 5 kg of active substance / ha is used for controlling weed seeds. The treatment against these plant species can be carried out before or after the emergence process. A particular advantage is that the compounds of the invention map a specifically high tolerance to agricultural crops, in particular to crops, potatoes, rice, soybeans and diabetes.

The compounds of the invention may be used either alone or in admixture with each other or in admixture with other active ingredients. Depotting agents, plant protection agents or pest control agents may be added, depending on the desired effect.

If it is desired to broaden the spectrum of efficacy, other herbicides may be added. For example, the active compounds from the group of triazines, aminotriazoles, piilides, diazines, urpciles, aliphatic carboxylic acids and halogenated carboxylic acids, benzoic acid substitutes and aryloxycarboxylic acids, hydrazides, esters, amides, nitriles, nitriles, nitriles, nitriles, nitriles carbemide and thiocarbamide, ureas, 2,3,6-trichlorobenzyloxypropoline, rhodane-containing compositions, and other additives.

Other additives include, for example, phytotoxic additives which can cause synergistic enhancement of the effect with the herbicides, such as among others, emulsifiers, solvents and oily additives.

Suitably, the active ingredients according to the invention or mixtures thereof are used in the form of preparations such as dusts, dusts, granules, solutions, emulsions or suspensions, with the addition of liquid and / or solid carrier substances or diluents and optionally wetting agents, tackifiers, emulsifiers and suspensions. or dispersible.

Suitable liquid carriers are, for example, water, aliphatic and aromatic hydrocarbons, such as benzene, toluene, xylene, cyclohexanone, phosphorus, dimethylformamide, dimethylformamide, according to the mineral oil fraction.

Mineral soils such as trnsil, silica gel, flour, kaolin, attaclay, limestone, silicic acid and vegetable products such as flour are suitable as solid carriers.

Surfactants include, for example, calclualignin sulfonate, polylylbutylbiphenyl ether, naphthalene sulfonic acid and salts thereof, sulfonic acid and their salts, formaldehyde condensates, fatty alcohol sulfates, and the sub-sulfonic acid and benzenesulfonic acid salts thereof.

The proportion of active ingredient (s) in the various preparations may vary within wide limits. For example, compositions comprising about 10 to 80% by weight of the active ingredient, about 90 to 20% by weight of the liquid or solid carrier, and optionally up to 20% by weight of the surfactant.

The formulations can be rooted in a conventional manner, for example with water as carrier in the spraying bed at a rate of about 100 to 1000 l / ha. It is also possible to use the compositions by so-called low-volume and ultra-small-scale spreading and application in the form of so-called microgranules.

The novel compounds of the present invention are reacted by reacting the acid esters in the presence of three bases such as potassium carbonate at 10 ° C and boiling point. the chloroform of formula II,

O — CO — Cl

(II) in which

R3 is as previously defined, with the amines of formula III,

r.

r ₂ x NH (III) where

R1 and R8 are as previously defined, and the products are isolated in a manner known per se by reaction.

Suitable solvents for these reactions are, for example, ethyl acetate, acetonitrile, hexane, benzene, toluene, methyl methane, carbon tetrachloride, tetrahydrofuran, dimethylformamide and other inert solvents to the reactants.

The reaction is carried out at temperatures between 10 DEG C. and the boiling point of the reaction mixture.

The following examples explain the preparation of the compounds of the invention.

He did

3- (2,2-Dimethylvallyylamino) -ethyl ester of N- (2,2-dimethoxyethyl) carbanilic acid

To a solution of 20.9 g (0.1 mol) of N- (2,2-dimethyl) -4-phthaline in 50 ml of ethyl acetate was added dropwise a solution of 28.3 g (0.1%) while stirring and cooling to 10-15 ° C. 1 mol) of 3- (2,2-diethyltropyltrloo) -4-oxoic acid and a solution of 13.8 g (0.1 mol) of potassium carbonate in 70 ml of water; Stir for 30 minutes at room temperature, then separate the organic phase, dilute with a small portion of ethyl acetate, dilute at 0 ° C with dilute hydrochloric acid and brine, dry with magnesium sulfate, and remove the solvent under reduced pressure. The residue was recrystallized from ethyl acetate / ptotto.

Yield: 36 g = 79% of theory

88-89 ° C.

Example 2

3- (Triellorrttylktrbfoyltmino) phtholytic acid N- (2-ylmethyl) -3-retylcyclobutyric acid

To a solution of 16.0 g of N- (2-cyclohexyl) -3-methylthiole in 100 ml of acetone was added dropwise 31.7 g of 3- (trichloro-tertylcarbotyl) trifluoromethyl chloroacetate in 100 ml of acetonitrile. After addition of 12.1 g of Ν, ·-dimethyl, the temperature is raised to 46 DEG C. The reaction mixture is heated to boiling for 10 minutes, cooled, stirred in 500 ml of ice-water and the precipitated substance is filtered after filtration. recrystallized from isopropanol.

Yield: 31.5 g = 72% of theory

Melting point: 118 ° C.

Example 3

3- (Tert-Butylktrbfylyl) tert-N-cyanomethylcarbalilic acid

To a solution of 13.2 g of N-cyano-ethylaniline in 150 ml of acetone is added. 25.57 g of 3- (tert.. ButylktrbfOylamino) ftnyltsttru ^ ^{3 <ζϊου} cHoimravenčí then with further íchj ^ ^ i ^ ne dropwise 12.1 g Ν, Ν-diretlУιaltliou and stirring was continued for 15 minutes under reflux. After cooling, the batch is stirred into 1 l of ice water, the precipitated substance is filtered off with suction and, after drying under vacuum, recrystallized from a small amount of acetone.

Yield: 24.0 g = 68% of theory

Melting point: 173 ° C.

208137. 6

Example

3- (Cyclopropylcarbonylamino) phenyl N- (tyl) carbanilic acid ester

29.2 g of N- (2-kethanethaniline) are dissolved in 200 ml of acetontril and then, with stirring, 23.97 g of cyclopropylcarbonylminophenyl chloroformate are added while stirring, the temperature of the solution rising to 35 ° C. The solvent is distilled off under vacuum overnight, the residual oily residue is treated with water, the water is decalcified and the oil is crystallized using isopropyl ether / isopropanol 1: 1, and the crystallizate is recrystallized from isopropanol.

Yield: 16.59 g = 48% of theory Melting point: 142 [deg.] C.

Example 5

3- (Propynyl amine) phenol ether of N-knan-ethyl-1-methyl-methylbenzamide

The potassium salt produced from 64.4 g (0.39 mol) of propionic acid 3-hydro-hydrimide is taken up in 300 ml of acetonitrile. P4 dropwise addition of a solution of 81.4 g (0.39 mol) of N -cyanone-N-N- (3'-methylphenyl) carbamonyl chloride in 250 ml of acetorntril increases from 28 ° C to 44 ° C with stirring at 5 minutes. It is then refluxed for 30 minutes. After evaporation under reduced pressure, it is dissolved in ethyl acetate and water, washed at 0 ° C with a small amount of dilute sodium hydroxide solution, dried with magnesium sulphate and evaporated under reduced pressure. The oily residue initially crystallized from ether.

VVěžek: 80.4 g = 61% of theory Melting point: Mp 97-99 ° C.

The following compounds of the invention can be prepared in an analogous manner

Name of the compound of the physical constant

3- (propinnylpino) phenylester and ethyl carbanil

3- (prnpinnylpmnn) phenylene ter carbanil

3- (propionylamino) phenyl ster -3-methylcarbanil

3- (prnpinnylaeino) feήyleeter karbanilové

(4-methylcarbanil) (prnpionylminine) phenyl ester

3- (propinnyllane) phenylphenyl-2-methylcarbanil

3- (propiornrolidine) -fluoro-3-methylcarbanilic acid

3- (prnpinnylaeinn) -4-ff enyeeter metylkarbanilové N - ^^ - dimetoxykyseliny lkyianmeylkyseliny N-N- ⁽² -kyymneyl) N- (2-methoxyethyl) N - ^ - Fyrnneyl) kyueliny N- (2-kymn eyl) N- (2-meeooyleyl) N- (2,2-dieeeoxylethyl) acid

mp 71-73 ° C

mp 130 ° C

mp 149-151 ° C

mp 71-72 ° C

mp 124-126 ° C

t. t. Mp 120-122 ° C

mp 82-84 ° C n ⁰ = 1.5343 table continuation

Compound name Physical constants

3- (propionylamino) phenyl N- (2,2-dimethoxyethyl) -3-methylcarbanilic acid ester 20 _ ⁿ D " 1,5405 3- (propionylamino) phenyl N- (2-bromoethyl) carbanilic acid ester t. t. M.p. 86-87 ° C 3- (propionylamino) phenyl N- (2-ethoxyethyl) carbanilic acid ester t. t. 83-84 DEG 3- (propionylamino) phenyl N- (2-cyanethyl) carbanilic acid ester t. t. 126-128 [deg.] C 3- (propionylamino) phenyl N- (2,2-dimethoxyethyl-2-methyl) carbanilic acid t. t. 105-107 ° C N- (1-cyano-2-phenylethyl) -N-methylcarbamic acid 3- (propionylamino) phenyl ester t. t. 104 ° C N- (alpha-cyanobenzyl) -N-ethylcarbamic acid 3- (propionylamino) phenyl ester t. t. 77 ° C 3- (tert-butylcarbonylamino) phenyl N- (2-cyanyl) -3-methylcarbonyl acid ester t. t. 122 [deg.] C 3- (tert-butylcarbonylamino) phenyl N- (2-cyanyl) carbanilic acid ester t. t. 118 ° C 3- (propionylamino) phenyl N- (1,3-dioxolan-2-ylmethyl) carbanilic acid t. t. 98-99 ° C 3-Methoxy-N- (2-methoxyethyl) carbanilic acid 3- (propionylamino) phenyl ester '20 ⁿ D ~ 1.5614 N- (4-methyl-1,3-dioxolan-2-ylmethyl) carbanilic acid 3- (propionylamino) phenyl ester _M 20, ⁿ D ' 1,5559 3- (2,2-dimethylvalerylamino) phenyl N-cyanomethylcarbanilic acid ester t. t. Mp 152-153 ° C N- (2-cyanyl) carbanilic acid 3- (2,2-dimethylvalerylamino) phenyl ester t. t. 93-95 DEG 3- (2-Methyl-propionylamino) -phenyl ster N- (2-cyanyl) -carbanilic acid t. t. M.p. 136-137 ° C 3- (2,2-Dimethylvalerylamino) phenyl N- (2-chloroethyl) carbonyl t. t. 101-102.5 ° N- (2-chloroethyl) carbanilic acid 3- (propionylamino) phenyl ester t. t. Mp 107-109 ° C 3- (propionylamino) phenyl N- (2-phenylethyl) carbanilic acid ester t. t. Mp 93-94 ° C 3- (crotonoylamino) phenyl N- (2-cyanethyl) - karbanilové t. t. M.p. 117-119 ° C N- (2-chloroethyl) carbanilic acid 3- (crotonoylamino) phenyl ester t. t. 131-133 [deg.] C

continued table

Name of the compound Physical constants 3- (2,2-Dimethyl-valyl-mino) phenyl N- (2,2-dimethoxyethyl) -carbonyl acid mp 77-79 ° C 3- (cyclopropylcarbonylmino) phenyl (R) N - (aminocarbonylmethyl) carbanilic acid mp 197 ° C 3- (cyclopropylcarbonyl) phtheteric acid N- (2-aminocarbonylmethyl) carbanil mp 166 ° C 3- (cyclopropylcarbonylamino) phenyl N- (2-cyanyl) -3-methylcarbanilic acid ester mp 175 ° C 3- (trichrrmttylkεr’bonylamino) felадrУe8ter N-cyrnneeylkkrbianil mp 102 ° C N- (2-cyanoethyl) -benzilic acid 1-trifluoromethyl-benzylamino-phenyl ester mp 137 ° C N- (2-methoxyethyl) carbanilic acid, 3- (t-tert-butylcarbonylmino) phthalene n * ⁰ = 1.5509 N- (2-methoxyethyl) -3-methoxycarbanilic acid, 3- (tert-butylcarbonylamino) phosphonate n ²⁰ = ¹ 5482 3- (cyllopropylcarbonylamino) phenyl 8 ter N- (2-methoxyyltyl) larbanilic acid mp 133 ° C N- (2-methoxyethyl) -carbanilic acid 3- (trichloromethylcarbonllerine) phenyl ester n ° = 1 ^£, 5804 3- (Trichloromethylcarbonylphenyl) phthalic acid N- (2-cyclohexyl) -3-ricycocarbonylilic acid mp 135 ° C 3- (2,2-direeylvalerllarinolfernyaster N- (2,2-dimethyl-1,3-dioxolan-4-ylmethyl) carbanilic acid mp 100-102 ° C 3- (cyclopropyllarbenzylminolfeen18ter) N- (2-ethoxyethyl) carbanil mp 109 ° C 3- (trichloromethylcarbonllarino) phenyl ester of N-klanmethyl-3-clarrlarbanilic acid mp 162 ° C N- (2,2-dimethoxyethyl) -3-methylcarbamic acid 3- (tert-butylcarbonylbenzyl) phenyl] methyl ester viscous Hey 3- (cyclopropyllarbinyl) phenyl 8-N- (2-hexylthyl) carbanilic acid t.'t. Mp 116-117 ° C N- (2-methoxyethyl) -4-fluorocarbanilic acid 3- (clylpropylcarbolnylananiline) ethyl ester mp 103-105 ° C N- (2-methoxyethyl) -4-fluorocarbanilic acid 3- (cyllopropylcarbonylminl) phenyl ester mp 77-79 ° C

The compounds of the invention are colorless, odorless, crystalline or oily substances which are readily soluble in acetone, dimethylformamide, isophorone, cyclohexanone, tetrihydrofuran, and dimethylsulfoxide.

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

(a) 2,2-Dimethylvaeic acid 3-hydroxymethylilide

To a solution of 327 g (3 mol) of m-aminophenol in about 1 L of ethyl acetate was added dropwise with stirring 400 ml of water and 76 g of magnesium pyrophorium with stirring 445 g (3 mol) of 2,2-dimethylvaleric chloride. 10-20 ° C. Stir for one hour at room temperature. 400 ml of concentrated hydrochloric acid are then added dropwise at 0-5 ° C and stirred for 10 minutes. Then, the organic phase is separated off, washed neutral with sodium chloride solution and dried with magnesium sulphate. Ethyl acetate was partially distilled off and pentane was added to the residue, whereupon the reaction product crystallized.

Yield: 550 g = 83% of theory

M.p .: 155-156 ° C.

By analogy, the following are obtained:

Propionic acid 3-haloidide

2-methylpropionic acid, 3-methyl-2-methyl-2-methyl-2-methylpropionic acid

3-h ^ <^ i ^ <^ ^r 3cx 0all ^ LD crotonic acid

t. t. 183-185 Noc: 2 ° C t. t. Mp 180 ° C t. t. 158-159 Noc: 2 ° C

(b) 3- (Propylamino) phenyl chloroformate

To a solution of 177 µl of phosgene in 700 mL of ethyl acetate was added 292 g (1.77 moo) of propionic acid 3-hydroxyainide. For stirring! and cooling to 10-15 ° C is then added dropwise a solution of 225 ml (1.77 mol) of Ν, Ν-phenylanilium in 300 µl of ethyl acetate. It is then 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, washed with brine, dried over magnesium sulphate and evaporated under reduced pressure. The residue crystallized upon addition of 600 ml of pentane.

Yield: 327 g = 81% of theory

Melting point: 72-73 ° C

By analogy, the following are obtained:

3- (2-Methylprospisiylanin) phthyl chloroformate 3- (krstoioylamini) phenylsstsr chloroformic acid 3- (2,2-diylsylvalersylamino) phenyl chloroformate mp 69-71 ° C = 20 id = 1.5327 np ° ^1, 5273

c) Chloroformic acid 3- (cyclopropoxycarbsiyl) phenylester

100 ml of phosgene are condensed at -20 DEG C., then taken up in 1 l of ethyl acetate and 177.2 g of cyclopropanecarboxylic acid are added with stirring at 0 DEG C. with stirring. mp 184 ° C. 121 g of lal-methylsilyllium are then added dropwise to this mixture with further cooling. After stirring for one hour at 40 [deg.] C., the excess phosgene is purged with a stream of nitrogen, the batch is cooled to room temperature and the ethyl acetate phase is extracted twice with 250 [mu] l of ice-water. After separation of the organic phase, it is dried over magnesium sulphate, the solvent is distilled off in vacuo and the residue is crystallized by addition of petroleum ether. 207 g (86% of theory) of the above substance with a melting point of 94 DEG C. are obtained.

The AoalogickT method is produced by:

3- (tert-butylcarboinylamino) phenyl] chlorine tetrachloride m.p. 75 ° C

3- (trichloromethylcarbonylamino) phenyl chloroformate η £ θ * 1,5786

The following examples serve to explain moon use and significant herbicidal effect. Compounds of the Invention ·

Example 6

The compounds of the invention shown in the table were sprayed on the test plants Solenum and Brassica in a greenhouse at a rate of 5 kg of active substance / ha, dissolved in 500 liters of water / ha.

weeks after treatment, the treatment results were evaluated, indicating no effect on plant destruction.

As shown in the table, destruction of the test plants was generally achieved.

Compounds of the Invention Brassica Salting 3- (propionyl-amino) fernrt. ^β · N- (2,2-dimethoxyethyl) carbonic acid 4 4 3- (propionyl ^and Rino) Fein ^г le8teo acid-N-kyιannreylkεa b8al01ové 4 4 3- (Poopionylarino) phenic acid ester N- (2-cyanethyl) -3-methylcarbonyl 4 4 3- (poopiooylarino) fenestest kyeeyioy N-mm eooχeeylkaobealilové 4 4 3- (propioolaιnino) alkyl fernrle8teo ^e Elina N- (2-f kyirno eyy -4-methyl tylkarbwiilové 4 4 3- (poopionlamino) phenleβteo acid N- (2-cyodoethyl) -2-methylcarboforil 4 4 3- (poopionylarino) fetn ^r L · Teo acid N- (t-butyl f methoxy -3-methyl tylkarbnoilové 4 4 3- (poopionylamino) phenyl ester of N - (-) - dimethylethyl-4-methylcarbanilic acid 4 4 3- (Poopionylamino-phenyl) N- (2,2-dimethoxyeyl-3-methylcarbniic acid) 4 4 3- (p: oopitnylal & ino) fetnù.e8teo cyeelioy N- (2-bromo-4-carbonyl) 4 4 3- (poopionylarino) fexn ^r le8tto kyeeyioy N- (t-butyl ethoxyethyl f karbniOlové 4 4

Brassica

Soleunum continuation table

Compounds of the invention

3- (propionylamino) phenyl phenyl N- (2-cyano) carbanil

3- (propiooylamino) phenylene ter acid

N- (2,2-dimethoxymethyl) -2-methylcarbamoyl-4-carboxylic acid

N-1-chloro-3-mityl-benzoic acid

3- (propioyylamino) phenylethyl tyseliyy

N- (1-cyano-2-ethyl-thiazol-1-yl) -4- (1-cyano-2-ol) thiazole]

3- (propioyylamino) feryl ester N- (alpha-cyanobenzyl) -N-nylcarboxylic

3 '(propioyylamino) fetyletter tyseliyy

N-1'-Dioxolay-4-yl-methylcarbonyl

3- (propioyylamino) -tetra tyseliyy

3-methoxy-N- (2-mono-oxymethyl) -carbayil

3- (ttyl-carbonylamino) -fexene-tetrachloride

N- (4-chloro-1,3,3-dioxolan-2-ylmethyl) carbanilic acid

3- (2,2-dimethylamino-phenylethyl) N -cyclyl tybaycarboxylic acid

3- (2,2'-Dimethylvaltrylamino) phenylethyl N- (2-cyanyl) carbonyl

3- (2-Methylpropnoyylamio) phthyl-N- (2-cyanethyl) carbanilic acid

3- (2 _> 2-Dimethylvaltrylemino) phthyl ester of N- (2,2- β-pentyl) carbonyl

3- (2,2-Dimethylthio-amino-methyl-N- (2-sulfonyl) ethyl) carboxylic acid

3- (propionylamino) fexylisulfuric acid

N- (2-chloroethyl) carbanil

3- (propnonllamino) fetal acid

N- (2-phthylthyl) carbonyl

3 '- (crotonoylamino) fetnrle8ttr

N- (2-ketenyl) carbamyl

3- (crotonoylod.no) Theory and ter acids

N- (2-chloroethyl) carbayl

3- _(2> 2-dimetylvalerylamino) fernУ.e8ttr kyseliyy

N- (2,2-dimm-tonxrin-carbonyl)

3- (cyclopropylcarbonyl) amino) phenyl-N- (2-cyanyl) carbanil

3- (ttrc · butylcarboln »amino) fexyl.esttr tyseliyy N-kiaii tylcarbayil continuation table

Compounds of the invention Brassica Solarnum N- (2-cyanyl) -3-methylcarbanilic acid 3- (tert-butylcyclohexyl) phenyl ester 4 4 3- (tert-Butylcarbbooylamino) phenyl N- (2-cyanyl) carbanilic acid ester 4 4 3- (Trihloromethyl-4-carbonylimino) -phenyl ester of N-1-tert-butyl tylcarbanilic acid 4 4 3- (tert-butylcarbonylamino) phenyl N- (2-methoxyethyl) carbanilic acid ester 4 4 3- (tert-butylcarbonylanino) phenylethyl N-4-methoxyytyl-4-methoxycarbamic acid 4 4 3- (clkloprcpylkarbclnl-aπino) ffen leeter ^r of N- (2-methylthiophenyl oxyethylene methyl) karbanilo Vé 4 4 3- (triḥ] lCoreetylkar'booylamino) Feio ^г le9ter N- (2-methoxy methyl) carbanilic 4 4 3- (Trichloromethylcarbonylamino) fernyl ester N- (2-methoxyethyl) -3-methoxycyclohexyl ester 4 4 3- (cyclopropylcarbonylemino) phenyl N- (2-ethoxyethyl) carbanilic acid ester 4 4 3- (cyclopropylcarbonyleeino) phenyl N- (2-hydroxyethyl) carbanilic acid ester 4 4 3- (Cyclopropylcarbonylamino) phenyl N- (2-methoxyethyl) -4-fluorocarbanilic acid 4 4 3- (Cyclopropylpropylcarbonyleeinc) phenyl N- (2-ethoxyethyl) -4-fluorocarbanilic acid 4 4 3- (trChhCoreethyl-4''bonylaeino) ^f- methyl ester of N-lq <α-ethyl-3 - carbohydrate 4 4 3- (tert-butylic acid) N- (2,2-dimethoxyethyl) -3-methylcarbanil 4 4 Njoše třeno 0 0

Example 7

In the greenhouse, after emergence, the plants were treated with the compositions at a rate of 3 kg of active substance / ha. To this end, the compositions were evenly dispersed over the plants. The evaluation was performed by bonntation, indicating = totally destroyed, = undamaged.

Here, the compounds according to the invention 3 weeks after treatment show high selectivity with a significant effect on weeds. Comparative means do not show this selectivity.

Compositions of the invention

CD β H 03 / > • ra CD *O PQ WHAT

Li - (2-cyanyl) -3- (propionylamino) phenyl, 3- (propionylamino) phenyl, 3- (propionylamino) phenyl N- (2-cyano) phenyl ester <6 [ethoxyxy] -3-biscarbonyl10

3- (propisiylamino) phthyl ester of N-] lylknllethyl-3-methylcarbonyl

3- (prspisiylamino C) irl irl irl ss tep tep a tep ((a ((((

3- (2,2-dimethylvklsryklmiis) fysylsster acid N (2-01 ^^ tyl) carbanil10

10 10 10 10 0 0 0 0 0 0 0 10 10 10 10 0 0 0 0 0 0 0 10 10 10 10 0 0 0 0 0 0 0 10 10 10 10 0 0 0 0 0 0 0 10 10 10 10 0 0 0 0 0 0 0

Comparative means (according to BE patent 686 239)

3- (Sulfuric acid) n-butylcramic acid salt 0 5 0 1 5 0 .0 0 0 00 0

3- (prspisiylaniniC) 'snylsstsr isobutylcarbamic acid 0 8 0 1 80000000

Claims (2)

Cementic agents, characterized in that they contain, as active ingredient, at least one phenyl carbamic acid of the general formula I, in which: R 1 -C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, di-C 1 -C 2 -C 1-6 alkoxy-C 1 -C 2 -alkyl, cyano-C 1 -C 8 -alkyl, halogen-C 1 -C 2 -alkyl, ficyc-C 1 -C 1,3-disoxyl-ethyl-2-methyl-13-dicyclohexyl-4-yl-2,2-dimethyl-1,3-isoxyl-4-yl-yl or aniniclabronomethyl, R ₂ phenyl (once or twice halogen and / or methyl and / or methoxy substituted phenyl) R 1 is C 1 -C 8 alkyl, C 8 -C 8 alkenyl, cyclopropyl or trichloromethyl, or represent, R | methyl or ethyl, R2 alpha-lyenbenzyl or 1-yyaH2-phenyyityl, Rj ethyl. . 2. A process for the preparation of 3- (allylbiphenylbenzoyl) phenylene carbanilic acid ethers as active ingredient according to item 1 of the general formula I, in which: R1 and R3 are as defined in claim 1, characterized in that chloroformic acid esters of the formula II are reacted in the presence of bases at temperatures from 10 DEG C. to the boiling point of the reaction mixture, O-CO-Cl (II) wherein R1 is as defined in 1, with amines of formula III, Ri X X ^х R2 NH (III) wherein Rf and Rg are as previously defined, and the reaction products are isolated.