IE44673B1 - Herbicidally active diurethanes,process for their manufacture and their use - Google Patents

Description

The present invention is concerned with new herbicidally active diurethanes, a process for the manufacture of these compounds and their use.

The selective-herbicidal action of diurethanes has already been 5. known (German Patent Specification No. 1,567,151). A satisfactory herbicidal action against weeds that are especially difficult to combat, for example Amarantus sp., Galium aparine and Poa annua, and a sufficient selectivity towards cereals and potatoes has not hitherto been established for these urethanes.

. The problem upon which the present invention is based has therefore been to provide a herbicide which, as compared with the known diurethanes, combines a better action against weeds with a better tolerability towards cereals and potates.

This problem has now been solved by the herbicidally active . diurethanes of the present invention.

. I The present invention accordingly provides diurethanes of the general formual I Λ . 2 14 6 7 3 in which R-| represents a halogenoalkyl group, Rg represents a phenyl, methyl phenyl, halogenophenyl, trifluoromethylphenyl or methoxyphenyl group, and . R3 represents an alkyl, alkenyl or alkynyl group, or R-j represents a hydrogen atom or an alkyl, alkenyl, alkynyl or halogenoalkyl group, Rg represents an alkyl, halogenoalkyl, alkenyl, cycloalkyl, . alkynylcycloalkyl, benzyl, phenylethyl, phenyl, methyl phenyl, ethylphenyl, halogenophenyl, trifluoromethylphenyl or methoxyphenyl group, and R3 represents a methoxyethyl group, and X represents an oxygen or sulphur atom.

. The compounds of the present invention are distinguished by a surprisingly high tolerability towards potatoes, cereals, maize and rice.

As weeds are difficult to combat and which can be combated by the active compounds of the present invention, there may be mentioned, . for example, - 3 4 4 673 Amarantus sp., Galium aparine. Poa anhua, Echinochloa crus galli, Setaria, Digitaria sanguinalis and Avena fatua.

The most favourable action is exhibited by the new compounds when they are used in the post-emergence stage. In this connection the herbicidal . action extends to many types of plants, for example Stellaria media, Senecio vulgaris, Lamium amp!exicaule, Centaurea cyanus, Amarantus retroflexus, Chrysanthemum segetum, Ipomea sp., Polygonum lapathifoil urn, Galium aparine, Setaria italics, Poa annua, Echinocloa crus galli, Digitaria sanguinalis, Avena fatua and Alopecurus inyosuroides.

. The amount required of the new compounds for combating weeds selectively is approximately 0.5 to 5 kg of active substance per hectare; when two or more compounds of the present invention are used the range of approximately 0.5 to 5 kg refers Of course to the total amount applied of these compounds.

The present invention accordingly also provides a herbicidal preparation which comprises a compound of the general formula I, in admixture or conjunction with a suitable carrier. The preparation may of course contain one or more compounds of the general formula I.

The present invention further provides a method of protecting a living , plant against weeds, wherein the area in the vicinity of a living plant - 4 44673 is treated with a compound of the general formula I.

The present invention further provides a method of protecting a crop area against weeds, wherein a crop area is treated with a compound of the general formula I.

. The present invention further provides a pack which comprises a compound of the general formula I together with instructions for its use as a herbicide.

The halogenalkyl groups represented by and R2 are advantageously bromalkyl or chloralkyl groups, for example a bromethyl or chlorethyl . group.

The alkyl, alkenyl and alkynyl groups represented by R^ advantageously contain up to 5 carbon atoms.

The halogenophenyl group represented by R2 is advantageously a chlorophenyl group.

. The alkyl and alkenyl groups represented by Rg and the alkyl, alkenyl and alkynyl groups represented by Rg advantageously contain up to 4 carbon atoms.

Preferred compounds of the present invention are the following: N - (2 - Bromethyl) - carbanilic acid (3 - (methoxycarbonylamino) - phenyfj un ester, 4 6 7 3 Ν - (2 - Bromethyl) - carbanilic acid (3 -(ethoxycarbonylamino) -phenyl] ester.

Pi - .(2 - Bromethyl) - carbanilic acid (3 - (methylthiocarbonylamino) phenyl] ester, . N - (2 - Bromethyl) - carbanilic acid (3 - (ethyl thiocarbonyl ami no) phenyl! ester, N - (2 - Chlorethyl) - carbanilic acid (j -(methoxycarbonylamino) phenyl] ester, N - (2 - Chlorethyl) - carbanilic acid £ -(ethoxycarbonyl ami no) - phenyl] . ester, '·.

P! - (2- Chlorethyl) - carbanilic acid (3 - (methylthiocarbonylamino) phenyl ester, Pi - (2 - Chlorethyl) - carbanilic acid (3 -(ethylthiocarbonylamino) phenyl] ester, . N -(2 - Bromethyl) - carbanilic acid (3 -(allyloxycarbonylamino) - phenyl] ester, Pl - (2 - Chlorethyl) - carbanilic acid (3-(1- methylpropynyloxycarbonylamino) - phenyl] ester, PI - (2- Bromethyl) - carbanilic acid (3 -(2- propynyloxycarbonylami no) 20. phenyl] ester, N - (2 - Chlorethyl) - carbanilic acid (3-(2- propynyloxycarbonylaminoj phenyl] ester, Pi - (2 - Bromethyl ) - 2 - methylcarbanilic acid (3 -(methoxycarbonylarnino) phenyl] ester, . Pi - (2 - Bromethyl) - 3 - chlorocarbanilic acid (3 - (methoxycarbonylarnino) phenyl] ester, - 6 10. Ν - (2 - Bromethyl) - 2 - methylcarbanilic acid (j - (ethoxycarbonylamino) - phenyl] ester, N - (2 - Bromethyl) - 3 - chlorocarbanilic acid ^3-(1- methylethoxycarbonylamino) - phenyl] ester, N - (2 - Bromethyl) - carbanilic acid [3-(2- methyl propoxycarbonylamino) - phenyl) ester, -4 i— N - (2 - Bromethyl) - 3 - chlorocarbanilic acid [3_- (2-methylpropoxycarbonylamino) - phenyl] ester, N - (2 - Chlorethyl) - 3 - methoxycarbanilie acid [T - (methoxycarbony1amino) - phenyl] ester, N - (2 - Chlorethyl) - 3 - trifluoromethylcarbanilic acid ^3methoxycarbonylamino) - phenyl] ester and N - (2 - Bromethyl) - 3 - trifluoromethylcarbanilic acid [T(methoxycarbonylamino) - phenyl] ester.

. The compounds of the present invention may either be used alone, in admixture with one another or with other active substances. If desired, other defoliating, plant protecting or pest combinating agents may be added depending on the purpose desired.

The action and speed of action can be increased, for example, by action20. increasing additions, for example organice solvents, wetting agents and oils. This enables the quantities applied of the active substance itself to be reduced.

Advantageously, the active compounds of the general formula I or mixtures containing them are used in the form of herbicidal preparations, for . example powders, strewable preparations, granules, solutions, emulsions or suspensions, with the addition of liquid and/or solid vehicles or diluents - 7 4 4.6 7 3 I and, if desired, of surface-active agents, for example wetting agents, adherent agents, emulsifying agents and/or dispersing agents.

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

As solid carriers there are suitable, for example, mineral earths, for example tonsil, silica gel, talcum, Kaolin, attaclay, limestone and silicic . acid, and vegetable productsforexample meals.

As surface-active agents there may be mentioned, for example, calcium lignin sulphonate, polyoxyethylene alkyl-phenol ethers, naphthalene sulphonic acids and salts thereof, phenol sulphonic acids and salts thereof, formaldehyde condensates, fatty alcohol sulphates and also substituted . benzene sulphonic acids and salts thereof.

The total amount of the active compound or compounds of the general formula I in the various herbicidal preparations may vary within wide limits. For example, the preparations may contain approximately 10 to 80% by weight’of active compound(s), approximately 90 to 20% by weight . of liquid or solid carrier and also, if desired, up to 20% by weight of surface-active agent(s).

The. active compounds of the present invention may be applied in the usual - 8 manner, for example, with water as carrier in quantities of spray liquor of about 100 to 1000 litres per hectare. It is also possible to use the active compounds in the so-called Low Volume-11 and Ultra-Low-Volume Method as well as to apply them in the form of so-called microgranules.

The production of these preparations may be carried out in a manner known per se,for example,by mixing or grinding methods. If desired, the individual components may be mixed together only shortly before being used such, for example, as is carried out inpractice by the so-called tank-mix method.

The new compounds of the present invention may be prepared by methods . known per se for the manufacture of similar compounds, for example by one of the methods defined below.

The present invention accordingly further provides a process for the manufacture of the compounds of the general formula I, wherein . (a) a compound of the general formula II O-COCL (II) nh-co-x-r3 in which Rg and X have the meanings given above, is reacted with an amine of the general formula III - 9 4 4673 HN R.

(III) '2 In which R-j and Rg have the meanings given above, in the presence of an acid acceptor, for example with the addition of an excess of the amine of the general formula III or an inorganic base, for example a sodium hydroxide solution, sodium carbonate or potassium carbonate, ora tertiary organic base, for example treit’nylamine, or (b) a compound of the general formula IV NH-C0-X-R, (IV), in which Rg and X .have the meanings given above, is reacted in the presence of a tertiary organic base, for example triethylamine or pyridine, or is reacted in the form of an alkali salt thereof with a carbamoyl chloride of the general formula V N-C0-C1 R„< (V) in which R-j and Rg have the meanings given above, each reaction being carried out at a temperature within the range of from 0° to 10Q°C, Or, if desired,when Rj represents a hydrogen atom, is reacted in the presence of a catalyst advantageously ah organic base, with ah isocyanate of the general formula VI R2-N=C=0 in which Rg has the meaning given above, or - 10 - ‘ (VI) 16 7 3 (C) a nitro compcund of tno general formula III /K1 in which R^ and Rg have the meanings given above (provided that they do not represent groups that are capable of being easily hydrogenated ), is catalytically hydrogenated, for example by means of nickel in . methanol, to form the corresponding amine which is then reacted in the presence of an acid acceptor, for example an inorganic base, for example a sodium hydroxide solution, sodium carbonate or potassium carbonate, or a tertiary organic base, for example triethylamine, with a compound of the general formula VIII Cl— CO—X—Rg (VIII) . in which Rg and X have the meanings given above.

The starting compounds for the process of the present invention are known or may be prepared by. methods known per se.

Some specific compounds of the present invention are listed in the following Table. - 11 4 467 3 TABLE 1.

Compound of Invention 1. N-(2-Chlorethyl)-carbanilic acid {3- (methoxycarbonyl ami no) -phenyl] ester 2. N-(2-Bromethyl)-carbanilic acid ^-(methoxycarbonylamino)-pheny'j] ester 3. N-(2-Bromethyl)-carbanilic acid (ethoxycarbonylamino)-phenyl] ester 4. N-(2-Bromethyl)-carbanilic acid (3-(methy1thiocarbonylamino)-phenyi3 ester . N-(2-Bromethyl)-carbanilic acid (ethyl thi ocarbonyl ami no )-phenyl] ester 6. N-(2-Chloretby1)-carbaniTic acid {3- (ethoxycarbonyl ami no) - phenylj ester 7. N-(2-Chlorethylj-carbanilic acid (3- (methyl thiocarbonyl ami no) -phenyl] ester 8. N-(2-Chlorethyl)-carbanilic acid (3-(ethyl thi ocarbonyl ami no)-phenyl] ester 9. N-(2-Bromethy1)-carbanilic acid ^-(allyloxycarbonylamino)-phenylj ester Physical constant M.p.: 98—100°C M.p.: 88—90°C M.p.: 80—82°C M.p.:118-120°C M.p.: 78—80°C M.p.: 71—73°C M.p. :122-124°C M.p.: 75—76°C Μ.Ρ.: 80—81°C - 12 44673 Compound of the invention physical constant N-(2-Chlorethyl)-carbanilic acid^3-(1-methylpropynyloxycarbonylamino)-phenyl] ester M.p.: 96—98°C N-(2-Bromethyl )-carbanilic acid (3-(2-propynyloxycarbonylamino)-phenyj| ester M.p. :105—106°C N-(2-Chlorethyl)-carbanilic acid(3(2-propynyl oxycarbonyl amino)-phenyl] ester M.p. :121-123°C N-(2-Bromethyl)-3-chlorocarbanilic acid[3(1 -methyl ethoxycarbonyl ami no) -phenyl] ester M.p. :102-104°C N-(2-Bromethyl}2-methylcarbanilie acid (3-(methoxycarbonylanrino)-phenyi] ester M.p.:108-110°C N-(2-Bromethyl>2-methylcarbani!ic acid )3- (ethoxycarbonyl ami no) -phenyl] ester M.p. :104-106°C N-(2-Bromethyl)3-ch1orocarbanilic acid (3- (methoxycarbonyl ami no) -phenyl] ester M.p. :100-102°C Carbanilie acid|3-(2-methoxyethoxycarbonyl ami no)-phenyl] ester M.p. :117-118°C N-Methylcarbanilic acid [3-(2-methoxyethoxycarbonylami no)-phenyl) ester M.P.: 70—72°C - 13 4 4673 Compound of the invention physical constant 19. N-Ethylcarbanilic acid ^-(2-methoxyethoxyca rbonyl ami no)-phenyl] ester M.p.: 82—84°C 20. N-Butylcarbanilic acid j3-(2-methoxyethoxycarbonylamino)-phenyl] ester n 20 = 1.5502 21. N-Ethyl-2-methylcarbanilic acid(3{2-methoxyethoxycarbonyl ami no) -pheny l] ester M.P. :117-119°C 22. N-Ethyl-3-methylcarbanilic acid(3-(2methoxyethoxycarbonylamino) -phenyl] ester M.p.: 89—91 °C 23. N-Ethyl -4-methyl carbani lie acid (3-( 2methoxyethoxycarbonyl ami no)-pheny ester M.p.: 96—97°C 24. 3-Methyl carbani 1 i c acid (3- (2-methoxyethoxycarbonylaminoj-phenylj ester M.p.: 89—90°C 25. 3-Chlprocarbani 1 ic aci d (3- (2-methoxyethoxycarbonylamino)-phenyl) ester M.p.: 87—88°C 26. N-Allylcarbanilic acid(3-(2-methoxyethoxycarbonyl ami no)-phenyl] ester M.P.: 66—68°C 27. N»N-Dimethylcarbamic acid ^3-(2-methoxyethoxycarbonyl ami no)-phenyl] ester s M.p.:113- 115°C - 14 44673 Compound of the invention Physical constant Ν,Ν-Diethylcarbamic acid ^-(2-methoxyethoxycarbony 1 ami no) -phenyl] ester M.p.: 69—71 °C N,N-Bis-(2-Chlorethyl)-carbamic acid (3- (2-me thoxye thoxyca rbony 1 ami no)phenyl] ester M.p.: 79—81 °C N-Ethyl-N-butylcarbamic acid (3- (2-methoxyethoxyca rbony1 ami no)phenyl] ester n 2° = 1.5164 Ν,Ν-Dipropylcarbamic acid ^-(2-methoxyethoxycarbonyl ami no) -phenyl] ester = 1 5157 Π D N,N-Dibutylcarbamic acid ^-(2-methoxyethoxycarbonyl ami no )-phenyl] ester η θ° = 1.5098 N-Butylcarbamic acid (3-( 2-me thoxyethoxycarbonylamino)-phenyl] ester M.p.: 84—85°C N-Propyl-3-methoxycarbanilie acid (s- (2-methoxyethoxycarbonyl ami no) phenyl] ester M.p.: 86—87°C N-Methy 1 -3-methyl carbani lie aci d (3- (2methoxyethoxycarbonyl ami no) -phenyl] ester n d° = 1-5620 - 15 44 67 3 Compound of the invention physical constant 36. N-Cyclohexyl-N-propylcarbamic acid (3- (2-methoxyetboxy carbonyl ami no)phenyl] ester M.p.: 86—87°G 37. N-(l-EthynyTcyelohexyl)-carbamic acid [3- (2-me'thoxyethoxycarbonyl ami no) phenyl] ester M.P. :128-130°C 38. Ν,Ν-Diallylcarbamic acid)3-(2-msthoxyethoxycarbonyl ami no) -pheny l] ester n o° -= 1.5302 39. N-Methyl-N-(1-methyl-2-propynyl)-carbami c ac i d (3-(2-methoxyethoxycarbonylami no)phenyl] ester η θθ = 1.5164 40. 2-Metbyl-N-propylcarbanilic acid(3(2-methoxyethoxycarbonyl ami no) -phenyl] · ester M.p.: 63—67°C 41. 4-Methyl-N-propylcarbanilic acid(3(2-methoxyethoxycarbonylami no)-phenyl] ester n J}0 = 1-5273 42. N,N-Bis-(2-bromethyl)-carbamic acid(3(2-methoxyethoxycarbonyl ami no) -phenyl] ester M.p.: 81—84°C -16 4 4 6 7 3 Compound of the invention physical constant 43. N-Pentylcarbanilic acid ^-(2-methoxy- ethoxycarbonyl ami no) -phenyl] ester n = 1.5166 44. N,N-Bis-(l-chloro-l-methylethy1)- carbamic acid ^-(2-methoxyethoxy- carbonyl ami no )-phenyl] ester η 2° = 1.5136 45. N-Butyl-3-methoxycarbanilic acid(3- (2-methoxyethoxycarbonyl ami no)-phenyl] ester n Q° = 1.5349 46. N-Butyl-2-methylcarbanilic acid(j- ]0. (2-methoxyethoxycarbonylami no)-phenyΌ ester n o° = 1.5290 47. N-Butyl-4-methylcarbanilic acid )3-(2- methoxyethoxycarbonylamino)-phenyl] ester η θ0 = 1.5340 48. N-Isobutyl-2-methylcarbanilic acid |3-(2- 15. methoxyethoxycarbonyl ami no)-phenyl] ester n o° = 1.5374 49. N-Isobutyl-3-methylcarbanilic acid )3-(2- methoxyethoxycarbonylamino)-phenyl] ester η θ0 = 1.5379 50. N-Isobutyl-4-methylcarbanilic acid[3- (2-methoxyethoxycarbonylami no)-pheny$ 20. ester n 20 = 1.5372 - 17 44673 Compound of the invention_physical constant 51. N-Isobuty1carban i1i c acid $3-(2-methoxyethoxycarbonyl ami no) - phenyl} ester „ 20 n D = 1.5346 5. 52. 2-Chloro-N-methylcarbanilic acid [3(2-methoxyethoxycarbonyl ami no)-phenyl] ester M.p.: 104 —1O6°C 53. 3-Chloro-N-methylcarbanilic acid (3-(2methoxyethoxycarbonyl ami no)-phenyl] ester M.p.: 62- -64°C 10. 54. 4-Chloro-N-methylcarbanilic acid (3( 2-methoxyethoxy carbonyl ami no )-phenylJ ester n 20 n D 1.5586 55. N-(2-ch1orethyl)-carbanilic acid{3(2-methyl propoxycarbonyl ami no )-phenyl] ester M.p.: 95—96°C 15. 55. N-(2-Bromethyi)-2-methylcarbanilie acid (3-(1-methylethoxycarbonyl ami no)-phenyj ester M.p.: 126—128°C 57. N-(2-Chlorethyl)-3-chlorocarbanilic acid (3(2-methoxycarbonyl ami no) - phenyl) ester M.p.: 97— -99°C 58. N-(2-Bromethyl)-4-methylcarbanilic acid 20. ^-(methoxycarbonylamino)-phenylj ester M.p.: 101- —103°C - 18 4467 Compound of the invention_ physical constant 59. N-(2-Bromethyl)-3-chlorocarbanilic acid)3-(lmethyl ethoxycarbonyl ami no)-phenyl) ester M.p.: 102—104°C 60. N-(2-Bromethyl)-2-methylcarbanilic acid (3-(methoxycarbonylamino)-phenyl] ester M.p.: 108—110°C 5. 61. N-(2-Bromethyl)-2-methylcarbanilic acid [3- (ethoxycarbonyl ami no )-phenyl] ester M.p.: 104—106°C 62. N-(2-Bromethyl)-3-chlorocarbanilic acid (3-(methoxycarbonylamino)-phenyl) ester M.p.: 100—102°C 10. 63. N-(2-Bromethyl)-carbanilic acid(.3-(2-methylpropoxycarbonyl ami no) - phenyl) ester M.p.: 82—83°C. 64. N-(2-Bromethyl)-3-chlorocarbanilic acid (3-(2methyl propoxycarbonyl ami no)-phenyl] ester M.p.: 60—63°C 65. N-(2-Chlorethyl)-3-chlorocarbanilic acid (3- (2-methoxycarbonyl ami no)-pheny l) ester M.p.: 97—99°C 15. 66. N-(2-Bi*omethyl)-4-methy1carbanilic acid )3- (2-methoxyca rbony 1 ami no) - phenyl) ester M.p.: 101—103°C 67. N-(2-Bromethy1)-3-chlorocarbanilic acid (3-(methylthiocarbonylaminoj-phenyl) ester . M.P.: 152—154°C - 19 4 461 3 Coriipound of the invention_physical constant N-(2-Bromethyl)-2-methylcarbanilic acid (3- (methyl thi ocarbonyl ami no)-phenyi] ester M.p.: 132°C 3-Chloro-N-(2-Chlorethyl)-carbanilic acid (3-(ethoxycarbonylaniinoj-phenyl] ester M.p.: 89—91 °C 3-Ch1oro-N-(2-chlorethyl)-carbanilic acid (3-(1methylethoxycarbonylamino)-phenyi] ester M.p.: 103—105°C N-(2-Bromethyl)-4-methy1carbanilie acid [3- (ethoxycarbonyl ami no) -phenyl] ester M.P.: 88—90°C 3-Chloro-N-(2-chlorethyl)-carbanilic acid (3-(methylthiocarbonylamino)-phenylJ ester M.p.: 140—142°C N-(2-Chlorethyl)-carbanilic acidfo-(1-methyl2-propenyloxycarborty]amino)-phenyi} ester M.P.: 82—84°C 3-Chloro-N-(2-Chlorethyl)-carbanilic acid (3-(2methylpropoxycarbonyl amino)-phenylJ ester 20 nD = 1.5514 N-(2-Bromethyl)-3-trif1uoromethylcarbani1i c acid (3-(ethoxyearbonylamino)-phenyl] ester M.p.: 73—75°C - 20 4 4 6 7 3 Compound of the invention_physical constant 76. N-(2-Bromethyl)-4-methylcarbanilic acid (3-(1methy 1 ethoxy carbonyl ami no) -pheny l] ester M.p.: 79—S1°C 77. N-(2-Bromethy1)-3-trif1uoromethylcarbani1i c acid [3-(methoxycarbonylamino}-phenyl] ester M.p.: 86—88°C 5. 78. N-(2-Bromethyl)-3-trifluoromethy1carbani1ic acid [3-(methylthiocarbonylamino)-phenyl] ester M.p.: 125—126°C 79. N-(2-Bromethyl)-3-1 ri f1uoromethyl carbanilic acid (3-(1-methylethoxy carbonyl ami no )-phenyl] ester M.p,: 85—87° 10. 80. N-(2-Bromethyl)-3-methylcarbanilie acid (3- (methoxycarbonyl ami no )-phenyl] ester M.p.: 106—108°C 81. N-(2-Bromethyl)-4-chlorocarbanilic acid (l-(methoxycarbonylamino)-phenyl] ester M.p.: 99—101 °C 15. 82. N-(2-Bromethyl)-3-methylcarbanilie acid (3- (ethoxycarbonyl ami no )-phenyl] ester M.p.: 99—93°C 83. N-(2-Bromethy1)-4-chlorocarbanilic acid (l- (ethoxycarbonyl ami no) -phenyl] ester M.p.: 80—82°C - 21 - 4 4 ®7 3 Compound of the invention physical constant 84. N-(2-Bromethyl)-4,-chlorocarbanilic acid methylethoxycarnonylamino)-phenylj ester M.p.: 83—85°C 85. N-(2-BromethyT)-4-chlorocarbanilic acid [3-(allyloxycarbonylamino)-phenyl] ester M.p.: 30—92°C 5. 85. N-(2-BrofflethyT)-3-methylcarbanilic acid (3-(1methylethoxycarbonylaminoj-phenyl] ester M.p.: 127—129°C 87. N-(2-Bromethyl)-3-chlorocarbanilie acid (3-(2propynyloxycarbonylamino)-phenylj ester M.p.: 115—117°C These compounds are soluble in acetone, cyclohexanone, ethyl acetate, isophorone, ether, tetrahydrofuran and dimethylformamide and are practically insoluble in water and light gasoline.

The following Examples illustrate the invention. Example 1 illustrates the - 22 4 4 073 process of the present invention for the manufacture of the compounds of the general formula I and Example 2 illustrates the herbicidal activity of the compounds of the general formula I.

EXAMPLE I.

N-(2-Chlorethyl)-carbanilic acid [3-(methoxycarbonyl ami no)-phenyl] ester.

Into a solution of 23 grams of N-(?-ch1orethyl)-aniline hydrochloride in 50 ml of water and 50 ml of ethyl acetate were introduced dropwise, while stirring a solution of 22.9 grams of chloroformic acid 3 -methoxycarbonylami nophenyl ester in 50 ml of ethyl acetate and simultaneously a solution of 30.5 grams of potassium carbonate in 150 ml of water at 10 to 15°C. The mixture . was further stirred for 30 minutes at 15°C, and then the organic phase was separated and diluted with about 100 ml of ethyl acetate, and washed at 0°C in succession with dilute sodium hydroxide solution, water, dilute, hydrochloric acid and water. After being dried with magnesium sulphate, the mixture was evaporated under reduced pressure. The initially oily residue so obtained . soon crystallized throughout and was recrystallized from ethyl acetate/pentane. Yield: 30 grams - 86% of the theoretical yield. Melting point: 98—100°C.

The other compounds listed in Table 1 above may be prepared in an analogous manner.

EXAMPLE 2.

In a series of tests carried out in a greenhouse the plants listed in the . Table below were treated at the post-emergence stage with preparations used - 23 44673 in such amounts that 3 kg of the active compound being tested were applied per hectare. As the agents used for comparision there were used the known compounds (1) 3-Methoxycarbonylaminophenyl-N-(S-methylphenyl)-carbamate 5· and (2) 2,4-Dichloro-phenoxyacetic acid.

The plants were in the young stage. The active compounds being tested were applied in the form of aqueous emulsions using quantities of liquid corresponding to 500 litres per hectare. After 14 days the results of the treatment were . evaluated and expressed by a numerical scale extending from 0 to 10, the . value 0 representing total destruction and the value 10 representing no damage.

The values listed in the following Table illustrate the good tolerability towards crops of the compounds of the present invention, whereas the known agents used for comparison caused considerable damage to the crop plants. - 24 44673 «—«. Z Π z rt Z rt Z »co»z o z Φ 1 ρ ι =r ι 3* 1 1 1 P 1 <+·’“*· ~S «j.<-s rt - ΖΓ N) cr ro O IO O IO ro io cr ro O 1 O 1 O 1 O 1 rt ι o 2, X Γ) 3 O oi cn P oo o co 3 co << 3- << =r -s rt rt rt Ο rt << -j O —» cr o CTO ,x S o P o P o o 3 O 3 << 3 P 3 rt rt 3 rt 3 Φ 3 ro o ro 3 ro cr Φ »1. Φ << rt << rt P rt -»· rt O rt 3 rt —J 3* —«3- “5 3* 3 3“ 3 cr O 3* Oi << p«< o^< O < *< 3 -· 3 —* o -j «Μ-* 1—» -d ·—* 3 1 «-»-* Ol «—· Ό «Μ-r 3 1 3 1 << 1 O 1 3 l 3· 1 Ο Π O O —« O 3* Π π ro n «Μ-r Ο» «—-P P P ro p 3 CU 3 P t -s ι -s 3 rt 3 rt Ο ί << -s ό cr Ό O’ -J. o- << o ‘—•cr '.cr 3* P 3* P 3 P ΕώΡ 1 p P Φ 3 ro 3 O 3 3 -σ 3 Φ 3 3 -J. 3 -J· ro -«· 3 -j. «Λ -J· << -J << -I 1 —> w —» ro —1 rt —’ J -J. ci·1· •o -·· rt —'· 3 -·· Φ -»·o o 3 O ro n << o rt o Φ ro ro rt ι» V) P Irt P 3 P P V— 01 rt O rt· n << n o Φ o Π Φ -ί· ro *»· ν=ϋϊ· mJ. C/5 — -5 O- rt o- a. CL rt- Cl Q. ro ICP tz> rs? 1 1 rt 1 t 1 z-s ro 3 rt 3 Ή* ro ro ro ro Γ+ rt r+ rt 3* zr zr 3* << << o O ««J x X 1 1 *< << 1 =3 < Φ =3 rt θ' co co CO CO co co . 1 o o Oo o O 1 -j —» mJ I LO © o o «mJ _4 ca f © o o o mJ —1 mU I 1 o o o o mJ -J -J _J o O o o o o o o o © o o o o o o o o © o o o a o o o © o o o o © © © o o o o σ o o o © © Ό © o o © o o o o o o ro IO © o o o o o o o o o co CO σι co o o o o 45b o o IO co © 1 co o ro to 1 I ro -J ro cn 1 1 1 IO kg of active substance per ha Potatoes.

Maize Wheat Barley Rice Stellaria m.

Senecio v.~ Lamium a.~ Centaurea_c.

Amaranthus r. Chrysanthemum s. fpomea p.

Polygonum c.

Galium a.' Setaria i’ Poa a.

Echinochloa e.g.

Digitaria~s? Ayena t.

Alopecurus m. o z ο ζ X 1 << ζ— Ό Ζ Ί I ο <—· o z < ct Z 3* I Cf z ΖΓ X π ro Ο ΡΟ Ό ΡΟ o PO Ο* ΓΌ o no Di 1 ευ ι << 1 OJ 1 Π 1 π x -5 o “ϊ OT 3 Ο T OT Φ O Oi o CT “Τ- CT -ϊ CT 3 -s 3- T 3* Ο —* ο ο O O cp —1 cr —» 3 O 3 3 Ο Ο 3 3 o o o o *< 5 . << φ X 5 <·< Φ- 3 -S 3 -5 —‘ffl —ι rt << Φ —x rt << Φ << Φ OJ ct Oi -S' Π cf φ ZS- —» rt ct 3 .3 3*< Φ 3*3 Oi 2Γ Oi 3* _j.k< •ι. —Λ 3 << 3 3 «< 3 —» 3 *—· cr —» S'—* O ' ο ι ο — o t 3 *— 3 —' *Ο 3 ι '—Λ O 1 O 1 ι n 1 Ci << ο 1 fl> —·η Ό O) -σ -s «—ι φ a -s i OJ X Oi zr -y 3- CT oj -s 3* cr σ -s •σ τ Φ CT Φ Ο 3 cr φ oj zr cr 3 cr 3 a 3 3 -j. cu 3 3 Φ tu Φ 0» << 3 «< 3 3 t< -j. 3 3 3 3 VZi^J ’“’«J* Ο -ί» tsi—- << -»j φ -»« Φ Ο | «-Xt Φ O '—‘.i. w o ΙΛ •σ η in Φ Ω φ a ct rt 0> 3* rt Oi ω (Λ Φ fi) Φ Ο Φ 0» Φ n cf fi rt OJ -5 Λ «5 -«· 3 η “? -*· Φ Π φ n fi* ‘c fi- ~s ->· -5 -j. a. «^ι>Ο« /CT' fi. fi. Ζ mCP 1 CC^\ /CT I ω ι i | - Ρ0 ct*··* {o •σ Φ —ι —j Φ 3 . -s , •σ τ > rt Φ ο •τ 3 sr cf •σ ο Φ << << 3 cf I << 3 3* << 3 tC I << 1 { GJ ώ GO co CO GO . | J 1 o o 03 1 —χ —1 —4 —X Ml Ο Ο o © o O -T © Ο o © © 1 _1 σ Ο o © o 1 _> . —» _i ο Ο o © o O ο Ο o o a o ΓΟ ο o o o o ο σ o © © © ο ο o o o p ο ο © © © © ο ο © © © © ο φ* o o o o ο ο o © © © Ρ ω I o © ο σ o o o © go ΓΌ 1 i 1 GO 1 ω Γ0 tn ro ο Ο © ro m! -0. •C* 1 1 [ 1 1 Ό Ο C □ CL w ο cf zr π> Kg of active substance per ha Potatoes.

Maize.

Wheat Barley Rice Stellaria m.

Senecio v.

Lanrium a.

Centaurea c.

Amaranthus Chrysanthemum s.

Ipomea p.

Polygonum c.

Galium a.

Setaria i.

Poa a.

Echinochloa e.g.

Digitaria s.

Avena f.

Alopecurus m. to to to co to to , -4 _4 —1 —4 o o o O o CO «4 o —1 o uo 00 03 o *4 «4 4 J «4 00 o o o o o *4 —J 00 o o o © o 4 _4 Ό © o © © © © © 1 o o © O - o co ! O © o o o o O σ o co © o o o 1 o o o o o 1 o o o © © 1 ro © © © © 1 o o o © - 1 1 I o © 1 o σ o o hi 1 1 tn to co 1 1 1 ( 1 4* ro III II - 27 Kg of active substance per ha Potatoes.

Maize Wheat Barley Rice Stellaria m.

Senecio v.

Lamium a.

Centaurea c.

Amaranthus r. Chrysanthemum s.

Ipomea p.

Polygonum c.

Galium a.

Setaria i.

Poa a.

Echinochloa e.g. Digitaria s.

Avena f.

Alopecurus m. Φ ω Φ co rf 1 rf 1 zr O 3 3 O 3- Ο Φ X —j X rf << o r3- n -s cu o φ —4 -s o τ n cr cu cr cu O -5 · o -s 3 O' 3 O’ «< CU M cu —i 3 —' 3 CU -j. &) -J. 3 —» 3 -1 «□. —Λ· U. -J. 3 n 3 Λ o O cu ---CU ι n ι n TJ -J. XJ 3* CL =T Q. ro ~ 3 /CO4 3^ 1 *< I .«rf/*™*' '—'no Φ ! Φ I (Λ 3- ω 3 rf Φ rf Φ Φ rf Φ rf T=T -S 3* Ο O X X s 2 φ ι rt m 3* ΓΙΟ 3 Φ I rf 4* 3* I O 3 X Φ << cf o ZT cu << -s —‘ cr o O CU ,3 5 << O’ —J & SU 3 3 -»* <<'O? ci ’ rf 2 3 I o m X cf O<< JU —a T I cr co ο I 3 3 << φ —1 rf 0) S’ 3<< 3* Ω O » I cr Ό CU 3*3 Φ -i· SjO ro cu ω o rf*·1· Φ O.

I no Φ 2 rf 1 zrm o dX 3· <<*< O -* co f -s no cr « O 3 3 ro << cf -'· o 3 0» O “5 φ —< 3 -1· << O rf Q. φ -s'w' Φ 2 rf I 3· CO O c X ,rf *< *< n —· cu π -s CO cr -5 o cr 3 CU << 3 CU —» 3 -«· -j. Ω 3 O CU Ω t -J.

“O O3*__t Φ I cdiro ι Φ 3 ω φ rf rf Φ 3* ’S I rf n> o << to CJ co Co CO 1 co _j aj o o 03 o o o wU __,- -4 _4 © © o o o o —ί- 4 ο o 00 © . © © —» _4 _, -4 © © o © © o —I _, O © o © © © o © © o O o 1 © —4 1 1 o © o o o o o o © ΓΟ co o o . 1 . Q o o o I o . o no © © _4 no no -P* © © no o CO © © 1 45* - Co 1 no 1 o no -Ρ» ω.

I I J=> I kg of active substance per ha Potatoes Maize Wheat Barley Rice Stellaria m.

Senecio v.

Lamium a.

Centaurea c.

Amaranthus r. Chrysanthemum s.

Ipomea p.

Polygonum c.

Galium a.

Setaria i.

Poa a.

Echinochloa e.g.

Digitaria s.

Avena f.

Alopecurus m.

I φ ζ Γ+» 3* Ζ Ο I *< Ξ ο XJ CU ·5 -5 ο §5 *< η Ml 0) a “ϊ 3 σ -I. οι 3 3 ο -J. ·—' π I -ο Φ φ ω ro Η· ι Φ 3 -S Φ Ο << I Φ ζ rt- I 3· m Ο rt X 3* << η —· ρ ι 3 ζ CT I ο σ* 3 C << S* —»<< 01 —ι 3 η -t· Of 3 5 ο σ· ·—· ο» ι 3 Ό ->· 3* η φ CU << Ο ωSet <+ ι Π) —· 1 |\> § rt Ζ Φ * rt Ζ =Γ I Ο 03 X -»· << ω Φ I rt·1—* 3* ro Ο I X Γ5 «< 3Τ Ο —' ο> Ο *5 ί σ* φ Ο Γ+ 3 3 *< *< φ ζ rt* =Γ Ζ Ο I χ σ << η φ » rt *5 Si «< 2 & cr 3 w ->· 3 3 -4. Ο Ο ι α> Ο I t< Ξ Ο 3 & φ -s rt σ-3ο*< 3 —' << Ο —I Φ a *5 3 cr Φ ζ rt 1 3* 5» Ο -J X —J << Ο —' & Ω *5 0, cr -ϊ ο σ 3 &> 3 ι ->· η 3 α> ο -ί ·*—» tr ι ευ Ό 3 3* -ί. φ η 3 << 0> 1=3« Φ (X <1 rt- 3 Φ Φ Ο *< I •σ &> =τ π φ -*· <3 & ν-ρχη Φ χιό ro rt I Φ 3 3 Φ ο << Ό Q. Φ Co> ±s ι << «=^γ Φ 3 ω Φ rt- rt φ zr -s ο << I < Φ rtθ’ X “J ro to CO 1 CO i co ω to -r1 -4 © O © © o co . _, o © © o o © . . o o o o a © -J -J o © o o o © —4 _4 -J _J o o o o o o co - © co 1 o 1 1 tn Ol 1 o o o - to 1 o I Ol - Ol 1 © _4 ro - © 1 o 1 1 1 1 1 o o 4=· o to 1 © - 1 o to 1 o 1 1 1 1 1 © 1 1 1 1 1 o I 1 1 I 1 to 1 1 oi 1 1 ·> 1 1 1 1 1 1 1 I 1 I cn I 1 1 1 1 1 I 1 1 1 1 kg of active substance per ha Potatoes Maize Wheat Barley Rice Stellaria m.

Senecio v.

Laurium a.

Centaurea c.

Amaranthus r. Chrysanthemum s.

Ipomea p.

Polygonum c.

Galium a.

Setaria i.

Poa a.

Echinochloa e.g.

Digitaria s.

Avena f.

Alopecurus m. 4 673 (5 ZZ ro s; ro ξξ ro s: ro z ro s2 ¢4- r rt· · «4* . J «4· I <4- « <4-w =r Ο XX =r-o rs* m 3 S O — ο << ο ro o -s o c O 1 X t χ η χ rf· ,x © X ch X © «< m c< - «< .3“ *<<< ·< -»· Cl Γ+ Λ Ο ο << Λ << Λ — α cr ro Ο 3* Q) —J «-I 0» O ro c -s<< *t ro - ί ϊ “5 1 -S-OJ -s .<+ er s CTX cr ω cr to CT S er<< o << ο << ο ι θ 2 o cr o —j s —> 3 3 3 3 3 3 GJ 3 n «< o << I Π> << ro << 3 << ro -J<< —-ζ —»«4· -J rt· mJ _J· -j -s Gi O PJ 8 QJ ” OJ 3 GJ O ro cr 3 _j 3 Ό 3 < 3 O 3 3 2> -J. © -«· “5 ta> mJ -J>x -j. GJ ** 3 3 =T 3 Ο □ Ο 3<< 3 O □ -1’ o ro Ο 43 Ο 0> © n o -»· o o »*< -m- OJ —‘Q. ι σ* I -Ϊ1 «μ ι ro •a — Ό Ο Ί3 0? •σ cr -0*^7 •σ n S'·—-. 3 Ρ> 3*3 3* GJ 3 Ϊ 3· ro f ro -τ ro -j» ro 3 ro ro cu 3 O 3 ςτ 3 -J· 3 ro ςς fy << ro t< -I. -J << « < CT C=i3 σώο ·=*§ ro ® ro ο ro ο» ro ro ¢4- ro ro w 3 <Λ w o W OJ £Λ XX Vi 1 <4· 3. <+ ro ¢4- —*· ch O Η- O <4- 3 ro o ro π ro cu ro ->· ro x ro ro -ί “ί • --y a. -$*< •S rS- a» Λ Α ! O 1 3 o · -j» 1 & $3- <·-. ) ro . 1 ΓΟ • 2 i 1 ι ro 3 3 ¢4- ro ΓΟ ro 3* ¢4- t <4- O rr a 3* X o ro ο ,x <+ X 1 << ST - *< ..1 . © I to to to to to co - -CO Ο ' t © - .© Ό - —ί «-j · mJ - - mJ mJ © Ο, to p o o tai Mi o . ο 00 o O © tai -J «4- - ο ο o © © mJ - -_J Ο ο : o © to Ό ί - © © CO r I -ι © ( co I *- 1 ΙΌ ΓΟ © a-1 © mJ- -.- -- ο o ro ce I «η tn o © . o oi ΓΟ . ΡΟ ’ o to mJ Ol ο · . ο o ro - 01 ο © © ro [ [ 4 I 1 1 1 *·.- ΡΟ: © ro I 1 1 1 1 -/ t i © mJ 1 1 υϊ 1 o Ϊ 1 Ί ί I 1 1 r 1 ~ I 1- t kg of active substance per ha Potatoes.

Maize.

Wheat.

Barley Rice Stellaria m.

Senecio v.

Lamium a.

Centaurea c.

Amaranthus r. Chrysanthemum s. . Ipomea p.

Polygonum, c Galium a.

Setaria i, Poa a.

Echinochloa e.g.

Digitaria s, Avena f.

Alopecurus m. - 30 44673 Ν-Pentyl carbani lie acid [3-(2-methoxyethoxyca rbony1ami no)-p henylj ester Z Φ M rt Z sr ι o CO X -J* << w Φ I rt*-'* 3* ro ο ι x cr << -s Ω O cu 3 *5 Φ S’? _lX_X ft» I 3 Ω -i. 3 3 *5 O σχ—· 3 ^3. =r Ω φ Ο» << n ’—'CL w *G3* rt I Φ φ Φ» c+ i 3· 2 Ο Φ X rt << ~r Ω << Ο» —λ -S I cr z ο I 3 -3 «< -r _u O ft, -o g<< —I. n o cu -— -s t cr xj & 3· 3 φ -»· 3 —» << -1. I—ftO Φ ft) (Α Ω rt -?· Φ CL -S Φ I rt 2* x £ Φ —J rt ι P ’ Ω © Oi «3 CT —J ω 5 * ·< -s -j O’ 01 OJ 3 O —ι» XJ Qj S’ ° Φ «u. S O- V ro s 1 3 Φ £ 1 ID rt -s © < XJ Ol Z 3” Ω » Φ -,· 3 3 CL Φ *< r-srt· t^UIT l Φ «—* —' (Α ΓΟ I rt J Z Φ 3 ι “ί Φ ·—* rt —· 3- I O 3 << ct&<< 3* —1 O I X no Μ I Ω X» 3 -S -5 O cr-σ o << 3 3 <<<< 3 *—» I Φ Z rt· ΖΓ Z O I χ σ << _j. O ft» 3 —ι 3-< O —· S O << ft* 3 -j. g 3 -«· Ο Ω χ—* 0» XJ Ω 3Φ CL cii l ifg -s rt 3* O I CO o to O lo a to 00 to I kg of active su per ha Potatoes. o mJ O o o o —1 o Maize. (0 »1 O o o «0 mJ o Wheat 10 o o o <0 wJ o Barley Μ» © o © o <0 mmi o Rice © o © O o Stellaria m. 1 1 1 I I 1 Senecio v. © 1 ro σ o o Lamium a. © 1 IO ro - ro Centaurea c. 1 © to o to Amaranthus r. © 1 •e» co o I Chrysanthemum s 1 1 o o Ipomea p. to 1 © © © o Polygonum c. I 1 1 1 Galium a. ro 1 to tn o to Setaria i. 1 1 I I Poa a. o 1 u t Echinochloa e.g ro 1 1 Digitaria s. 1 1 1 1 1 Avena f. 1 1 1 1 Alopecurus m. - 31 4 4 6 7 3 rosz ro . ro z ro z ro z ro oj cf I cf 1 cf 1 c+ ι cf ι V) Ω » cr 1—« zr cn zrco zred rf -J.2* O (/) Ο ΙΛ o c o c o c ro a ι X o X o .X cf X.cf X cf ' r-iCD *α?4. «< cr i< cr <<<< << << << << n c n c n —· n —» Ω —1 ι ω oj <-f 0> .cf OJ 1 ro ι OJ 1 4·«. I *5 << -s << •5 •y ro -Ϊ CO ro4-.· cr —* cr —» cr » cr ι CT 1 1 Ο ί ο I O 3 O 3 o 3 3 I 3 W 3 ro .3 ro 3 ro .3 ro ro o << 1 *< I << rf < rf << cf Cf 3* •4 g 43 -4 3- —* ΖΓ -4 ΖΓ 3* —» OJ (O oj ro 0J << s*< OJ «< o o 3 rf 3 cf 3 3 3 —' X *5 =r 4. 3- n -»· π Ω << o 3<< 3*< 3 OJ 3 OJ 3 OJ ro ι O —' o —· O -5 o ~s o -y rf -j — π *—Ώ ·—· σ- ·—Cr Ο- 3* 1 1 OJ 1 O’ ι OJ ! O> Ι OJ o 3 XJ -y XJ -5 XJ 3 XJ 3 X> 3 ,X «> 3- cr 3· cr 3 4. zr-«. 3* 4. << cf Π3 0» ro o> ro —> ro —· ro —* Ω 3* ,3 3 3 3 3 3 4. 3 4. O’ << << 4. << 4. << O Ω << Ω -y —· *Q> ^OJ cr ro O cf ro n ro n ro n ro ω ro. ω ,3,3* (Λ (Λ (Λ ω -j· W 4, rf CO cf OJ Cf o. cf CL cf a -4 4J ro ω -s -** ro ω · -y ro . -s'co' 5C? ro . -s'co' OJ «—» 3 1 O- T Cl 1 1 4*. 1 ->· Ω 3 OJ ’co' ro l ro ro 1 S3· 4~* a 3 3 1 QJ ro ro , ro ro ro •o g 4 I rf rf • rf 3* 3 3 zr 3 zr ro ω ro ro o O o 3 rf rf X .X X «< zr 3* << C=J o O 1 1 1 «< kg of active substance per ha Potatoes.

Maize.

Wheat Barley Rice Stellaria m.

Senecio v.

Lamium a, Centaurea c. Amaranthus r. Chrysanthemum s. Ipomea p.

Polygonum c.

Galium a.

Setaria i.

Poa a.

Echinochioa e.g. Digitaria s. avena f.

Alopecurus m. 46^3 XJ z Φ -P* Φ CO Φ ro Φ z Φ z “5 1 rt ι rt 1 rt 1 rt 1 rt 1 O 3 © 3 © 3 © 3 »-i 3 w XJ ro 1 O 3 © 3 O 3 Ο (rt O (rt o X —1 X —) X —1 X o X o X © << o << © .*< o << 3 << 3 c< 3 ω -s Ω *5 π -s n c Ω C o fi) o fi O fi) o fi rt fi .rt fi O J ) -S 1 -Ϊ 1 -s << -S << -ί -S cr z σ z σ z 3 —' cr —1 rt Φ ο 1 O 1 o I Ο Ω O 1 o rt 3 3 .□ 3 3 a 3 fi 3 4* 3 3 << ro << ro << ro << -s Λ Ctf << —* rt· rt mJ rt mJ cr -j g «J fi 3 0) 3 0) 3 fi fi fi ro fi 3 << 3 << 3 < 3 3 3 rt 3 1 mIi mJ -j. y Ω 3 Ω 3 n s’ ω 3 —‘ □ << 3 fi) O fil O fi) O fi O -*· o —’ o T ·— “1 “5 ·— “5 ·—- Ω cr ι σ 1 cr 1 3 1 1 fi 1 a XJ fi XJ fi) XJ fi XJ fi XJ “Ϊ XJ 3 3 3 3 3 3 3 3 Ω 3 3 3 ro ->· Φ -«· ro -j· φ φ fi Φ - · 3 —» 3 —· 3 —· 3 CL 3 3 3 << -j. -4. t< -1. << r-x l< a4. << ci Ω 'fi) ^li*) Φ fi» ©3« Φ fi Φ fi Ci« Φ X— ci 3? Φ Ω φ o ΙΛ Ω σι n V» o ω ro tA Irt rt —·» rt -)· rt -j· rt J, rt fi rt- CL Φ CL Φ CL Π> Cl ro 3 Φ Ω Φ -5 τ? ’τ? ’’ES' -s ro rt S -*· o. 1 1 I 1 3 O CT ro 1 ro ro ro X t 1 1 1 ζ— a a a 1 ro ro ro ro t rt rt rt rt a 3 3 3 3 ro << O O O rt mJ X X X 3 1 << << o 1 1 1 X *< 1 CO co co co co co . © 1 1 1 ί o -o CO 1 1 1 © . o 1 f © 1 © co 1 1 00 1 o mJ mJ Μβ) o © o o o © o o © 1 © © - 1 1 1 1 1 © © © ro © © © © © cn © © o o © 1 o mJ © © o I © © co o © ί © 1 o 1 ro I mJ I 1 I o I © j 1 o 1 o 1 © 1 CO 1 © CO 1 cn 1 1 1 1 - o o ro © - ro 1 © 1 © t ro 1 © ro | 1 1 1 co 1 1 t 1 1 CJ1 ί © ο =3 XJ Ο < Φ kg of active substance per ha.

Potatoes.

Maize.

Wheat Barley Rice Stellaria m.

Senecio v.

Lamium a.

Centaurea c.

Amaranthus r. Chrysanthemum s Ipomea p.

Polygonum c.

Galium a.

Setaria i.

Poa a.

Echinochloa e.g. Digitaria s.

Avena f.

Alopecurus m. 44673vOq.sa [iX'i23i,|d-(ouLmei.iuoqus3A'xomaiu)-cj PL3B Ol LLUBqJBOOJOtljQ-e-C ^494011(3-2) 3 Z σ 3 τ?ζ S?z z ro r rt 1 < 1 t 1 —I t rt*-^- o /xro xr ro .ro ro ι i 3 ro 3 ro. ο I ro « ro « —»co x w 3 co rt cr . rt 03 -a -s *< rt ro rt zr cr 3- -j rt o π o rt o o —J 2 o s - p a 3-3 ,x o •o ro rt ro o ro «< rt ro ro O rt cr rt X rt λ ro rt rt X ,3* O 3* . << =r P rt =r 3“ l< C- 3 << ok rt ,=r O *< o —’ t< mJ P -j cr<< X —* P — rt '«—* o -J «<*-* rt ι P 1 cr ί- S'—' rt r cr ω 3 O ο << I p ro ο 1 -j. p 3 1 -eJ OJ rt ι 3 n 3 .-s << 3 P 1 cr 3 << =T o cr — 3 n o ro mJ -M M4 QJ P rt -ι. 3- ,3 rt P o I 3 3 =r 3- mJ << ,3* a rt Ό Ml. 3.t< o o _j<< -j. o 3 mJ —' rt qj 3 n ro -*· © n 1 ©.3 2 O P 3 n *3 O -J. p *—· rj << i rt ZS- P 3 -$ i cr .—J,P •Ό O ro -s o cr •σ p VmUq 3· P 3 cr —> P 3 3 ro -j» ro 3 *< Oi 1 3 ro -»· ω &. '3 Ml. ri3 Ό -J. 3 —* rt.___ << mJ cr —· << rt ro*u? ro —ί ro -»· rt « (rt 3 rt ImJ ro rt n << ro p lo US P ro Λ ΙΛ o - 1 rt n rt p u-Jn rt ·«*· 3 ro -4* rt ro -*« ro cl ro rt o- mJ. ω ex rt 3* Cl ro ι rt · *·* mJ r> o a Ό O c SV» o ~h fD rt ro ι ι co ¢0 ω W·- L ω 04 mJ „ , _j 1 1 mJ . 1 © O ©' •*4 ' o mJ 03 mJ cn *-4 © mJ CM © © CO cn o mJ mJ cr o o © cv © I 1 i co oo © o co o © © Ca) © co © © o 1 ©. - © © o hi © ω o © ro o © © © _ © . © © 00 o © © © o mJ o mJ © mJ o t 1 o 4=» o © © o 1 1 t I o 1 o -0 mJ ©’ _© 1 1 . I 1 l\3 l_ 1 ί i. - '© © 1 1 1 1 © © 1 I III I I I I . I . 1 - I kg of active substance par ha Potatoes Maize Wheat Barley Rice Stellaria m.

Senecio v.

Lamium a.

Centaurea c.

Amaranthus r. Chrysanthemum s.

Ipomea p.

Polygonum c.

Galium a.

Setaria i.

Poa a.

Echinochloa e.g.

Digitaria s.

Avena f.

Alopecurus m. - 34 •J 4 6 7 3 N-(2-Bromethy!)-2-methylcarbanilic acid (3- (ethoxycarbonyl ami no )-phenyl] ester *t^2 1 1 2 -J | C?2 i 1 3 ro 3 rv 3 no Φ 1 Φ 1 rf CD rt CD rf CD =r ~s =r -s 3* -S o o << o o o X 3 —/3 X 3 φ Φ Φ << Φ n rf rf rf n rf qi sr 3- 3* cu 3* 3 << O << “5 cr —' X —« σ· —ι o <<«*-* o 3 1 Ω 1 3 1 t< no cu co c< 42, -S 1 J I Φ 3 cr Π cu 3 3 Φ O 3· 3 Φ -/. <4· 3 -J —j. c+ 3 3* << O 3 3· O << -i-S O << —-1 Q> O —1 ι n 3 n 1 Π •Ό fi> -J. Qj TJ cu 3 “5 3 “5 3 -S Φ cr o cr φ cr 3 Q) cu 3 Φ '< 3 1 3 << 3 —i —i. Ό -*« —1 — 3* —· V-/_l Φ —’· Φ Φ w n □ r> 71 Π rf rf Φ cuL—1|Qj Φ α» 1 Ω ‘o S Π φ -/. CL ΙΛ CL ί?σ *5 l ex to I to I to j to | to 1 1 1 1 1 —1 1 o CO o cr. —I -u —J 00 o o o co -J « co 1 o ! o 1 o 1 © 1 1 © 1 © 1 © 1 © 1 © © tn no © © o © o o o © o © o o o © o o o o o o o © o 00 *v) -* -J o 1 o I o 1 —J I © | 1 © i —»> 1 o 1 © 1 © kg of active substance per ha Potatoes Maize Wheat Barley Rice Stellaria m.

Senecio v.

Lamium a.

Centaurea c.

Amaranthus r. Chrysanthemum s.

Ipomea p.

Polygonum c.

Galium a.

Setaria i.

Poa a.

Echinochloa e.g.

Digitaria s.

Avena f.

Alopecurus in. 3 ω -•χ ω 'w'z Z ro i I 1 —* i I 1 1 i 3 * rt o ·**»—* » O *-X O ro *·*. 3* 3 ro 10 3 3“ ro 3* 3 ro rt 10 << rt I ro -1 rt —J ro 1 ,3~ 1 —1 O =r C3 rt O 3* O r1· © << 03 rt 1 0 -s =T “5 0 -s S’-s —1 -s 3 O X 0 << O X 0 << 0 rt 0 -1. | 3 —« 1 *< 1 — 3 =r 3 O Z 0 ro ro z η z rt ro -1. n> Ω 1 ro rt rt 1 ro 1 3* rt © rt 3 -$ 3**-x “S*-* ->· =T Ω 3- •5 ro ΕΓ<< o ro cr ro O << ro t< cr » o —t x 1 0 1 Ω —j -s —J o o 3 ' << 0 3 0 Q) ©-χ—’ 3 cr << t Ο 3Γ << ar -s 1 O I t< _r ro —1 —1 —J cr ro 3 ω —ι O ro ι *5 0 ro 0 0 1 t< » 3 Ί 3 3 cr -s 2 -S ,3 3 —» Ω 3 ro -1. ro 0 ro -a. ro tc ro ro 3· —1· c+ 3 rt 3 rt 3 rt —J rt 3 -j 3 3 O S' << 3· O 3‘ ro 3· -a. 0 O << -»«< x~*t< 3<< 3 *5 —1 I —« ro —» —-2 Ο O ί X—* XJ Ω. 3 *-* XJ x_> 3 I ·*-> Ω XJ 1 3“ ro -1. 1 3- 1 Ο Ω 1 ro 3* n ro -s 3 O ro 0 >—ro xj -$ ro ro 3 σ 0 ro 3 ro I -s 3-cr 3 “5 << ro χ-^-s << -5 . xi cr ro ro σ ,r?.3 1 cr t—',σ- 3- p 3 3 xj ro 'ro ro 3 << -»· t=— ro —a =r 3 ro 3 3 0. ro 0, tA Ο» ro 0. . W -*· << -_j x*™·' -j. (A —a rt n 3 -a rt —» rt-fr -a· ro ω • rt -»· ro << -J, ro -· Ω ΙΛ ro 0 -5 3 βώο -5 0 . ro rt ro -$ Ω ro ω ro ro ro ro rt Ω -5 -j. o CL ω n n ro -j· -j. rt 0. $ CL Cu ro Cl Cl «73* *7T> t η ο c a. in O -I> c+ ID ω CO to to CO co mJ mJ mJ 0 0 O O 0 0 _· mJ mJ «pj M« 0 © O © 0 O —a' . —a mJ O 0 © © GO CO -J Ml Ml Μ» to © O O 0 co -4 mJ mJ to 0 © © to co 0 © ό O © © © 0 © © 0 0 o 0 © O 0 0 0 0 © O 0 © 0 0 o © © 0 0 © © © © © © © © © 0 © 0 ro © © 0 0 —a 1 ω mJ I ro 0 © © © 0 © . 1 I I i I I mJ ro mJ 0 - © © © © 0 © kg of active substance per ha Potatoes.

Maize.

Wheat Barley Rice Stellaria m.

Senecio v.

Lamium a.

Centaurea c.

Amaranthus r. Chrysanthemum s.

Ipomea p.

Polygonum c.

Galium a.

Setaria i.

Poa a.

Echinochloa e.g. Digitaria s.

Avena f.

Alopecurus m. «14673 N-(2-Bromethyl)-3-trifluoromethylcarbanilie acid ¢- (methoxycarbonyl ami no) - pheny IJ es ter no φ ι c+ co (<* o φ s rt rt O«< Π I a 4* Ϊ I cr 3 ο Φ .3 rt £U m! a -I. Di 3 -S o cr 0) 3 -a rt ί 3* CO O S D> it •5 ,3 cr<< O — << γ Mi tO Ο» 1 3 rt -1. «5 □ -«· O -h no ι « o 3Φ -j n- o 3“ -s << o Ml I Ό Z o X << Π “5 _* «< << C —> —i O 0) —z -3 3 ι “S hi O I •a a Φ 3* 3 M* t< o Ml ϊ Ο Φ X rt < ,3* o < {U Ml “S CT I ο n 3 A> << T M. Q* Oj d> 3 3 Ml φ t< ΙΛ —· rt n Φ cu -S -Ϊ cr W CL Φ << Ω Γ+ CL So I X3 Φ 3- n Φ -J. 3 CL *< feiV Φ » w Φ 3 -ϊ Φ tO to to to to , . Ml Ml © © o o o mJ Ml mJ © O o o o . m! mJ _, O O © o o Mi mJ mJ mJ mJ O © o O o mJ •nJ mJ © o o © © © © © © © © © o o © o o © © © o © © - o © © © o o © © o o o o to o o σ hi o o o o o hi o 1 1 o - © hi 4* 4* I ί 1 i en 1 43» 1 1 Ml CO Ml hi to © I tn | I i I I I I kg of active substance per ha Potatoes Maize Wheat Barley Rice Stellaria m.

Senecio v.

Lamium a.

Centaurea c.

Amaranthus r. Chrysanthemum s.

Ipomea p.

Polygonum c.

Galium a.

Setaria i.

Poa a.

Echinochloa e.g.

Digitaria s.

Avena f.

Alopecurus m.

I I ra ro <4- 8 3· ro o -y X o • © ro Qj rt· -y zr er<< o—· 3 ·—* —» CO ro ι 3 3 Μ», φ 3 Γ+ I — Ό © s- ro ro «y 3 cr << ro ro —ι ω *j· rh © ro y ro o So's 'gTs ©ns i I 1 f ro ro i 1 T -» -5 —· 3 ro 3 ro cr σ ro 3 ro ro ι ro < o ro 8 ra ι r+ 03 <4· © 3 3 © «4· ro 3· -y 3- -y t< -y cr *y o o o o —» —» o << o X 3 x 3 ro *j· 3 -- 3 << ra < ra 3 © ro rt- ro n rf n rt- Mil rt· 3 rt· ro cr ro 3* 3 ro ,zr -J. 3- -5 << S«< o © << O<< cr —‘ Or — •m* —J. mJ © —» o - O ’ 8 CX*—* ro •—j 3 t 3 I •σ m « -y i << 42» << ω 3X0 CO cr co —* I ra ι ι O 1 ro © ro 3 3 *—* ¢+ ,3 3 3* 3 ra «< -* -s << 2 mJ. mJ Ml. ¢+ «“4 | -Ji 3 O 3 3 “3 “h ro -4) o -y o<< ra ra —«3 -.

I © ό ro =r “i ro cr & << 3 ro -j* w © rt· ro ro . *y © ι © Ό ro =r -s ro cr 3 ro << 3 w © rt· ro ro •y © ΙΛ r+ C ¢4-3-0 ro *< -y -y —ι o ro 3 «+ ro 3Γ f+ §<< O £3 3 a ra = t+ ro s.3 << < -* ein B) ro -s VI cr (+ B< ra a 3 gj GJ GJ GJ GJ mJ mJ mJ -j O © o O © mJ mJ mJ o OT co © o mJ -4 mJ o 00 o OT o _j mJ OT OT I © © mJ co OT 1 © © © mJ © © © © ro O © O O o O o o o 4* o o © o i o o © o © © © © © 4=* © © © o © © GJ © © tn © © o © © •TO - 1 o 1 42» 1 co cn 1 1 I . 1 1 42* CO Ϊ tn ro OI t 1 ro 42* 1 1 kg of active substance per ha Potatoes.

Maize.

Wheat Barley Rice Stellaria m.

Senecio v.

Lamium a.

Centaurea c.

Amaranthus r. Chrysanthemum s.

Ipomea p.

Polygonum c.

Galium a.

Setaria i.

Poa a.

Echinochloa e.g. Digitaria s.

Avena f.

Alopecurus m 4 6 7 3 2,4-Dichloro-phenoxyacetic acid > 'te'z 'CS'Z 2 ZZ 1 1 © i 1 1 1 ro ι 1 1 ro cf «—«· tc ro 3 —> ro ro ro zr ro ro ro ι rf rf ι i «4 | << I rf 1 3 3* (Λ 3 co —I co —· OT zr ro ro o ro -y << *y ro s O S rf X “h rf O -j o rf O X S =r<< O 3 3 O 3 zr 3 << 3 *< o “Ϊ << ro x ro o ro ω ro —' {V —» rf << rf X rf 0J rf Ω ro zr Ω 3- zr y ,zr 3- cr O rf*< OJ *< Ω «< cr<< ro o 3 3* — -J —1 0j — o —· □ 3 3 o CJ·*—* •y - 3 <<,<< OJ X » O 1 cr I *< L -y << CJ 3 45» O 4* —1 4S. o—' QJ Ω » << 1 3 i OJ 1 1 3 ω o> 3 —j o «< Ω 3 Ω Ω 4. O 5 fD 0> ZT —»zr 4. zr OJ 3 3 cr rf 3 —1 O> — 3 -4 s o O .3- -I. o 3 O o o cr-d 3 << 3 3 4. -J - -s OJ 3 «< —. o o 3 O ! o 3 ro —« O —* Ω Ο Ω XJ Ω 0> 3 0J OJ ( 0) * OJ zr oj rf<< 3 -S •σ *y 1 -s ro -y ro —1 1 4. σ 3” cr Ό CT .3 σ 3 OJ ro o> zr oj << o> o 3 3 3 ro 3 %r~l> 3 t< 4. 3 -J· ci- — Ξί ro ·—* X3 4. W 4. ΖΤ Ω ro ω’ ^ω rf Ω ro in ro ro - 3 O' rf OJ in o> -y oj n ro n rf Ω Ω ^4,4. CL “5 CL ro -. -5 CL 4. CL ro l/i 'w' rf 1 ro «· y —* < Φ C+ o’ CJ CJ tc tc | I CO © o © © o o o o o o o © © © o o CJ © fO —1 to —ι tc 4* 4» tn tn ro tc tn © o o © —· © 45» © O O ro o © o o o o o © © © CJ © o © © © © o o o © o © o o o o o © ro © o o -4 O I © I 1 I I * I i I kg of active substance per ha Potatoes Maize Wheat Barley Rice Stellaria m.

Senecio v.

Lamium a.

Centaurea c.

Amaranthus r. Chrysanthemum s. Ipomoea p.

Polygonum c.

Galium a.

Setaria i.

Poa a.

Echinochloa e.g. Digitaria s.

Avena f.

Alopecurus m. 44673

Claims (10)

1. A compound of the general formula 1. in which Rj represents a halogenoalkyl group, Rg represents' a phenyl, methylphenyi, halogenophenyl, trifluoromethylphenyl

2. A compound as claimed in claim 1, wherein ίη represents a bromalkyl or chioralkyl group.

3. A compound as claimed in Glaim 2, wherein R^ represents a bromethyl or chlorethyl group. - 40 44673

4. A compound as claimed in any one of claims 1 to 3, wherein Rg represents a chlorophenyl group. 5. 79. A process as claimed in claim 78, wherein the inorganic base is a sodium hydroxide solution sodium carbonate or potassium carbonate. 80. A process as claimed in claim 78, wherein the tertiary organic base is triethylamine. 5. general formula VIII Cl—CO-X-Rg (VIII), in which Rg and !( have the meanings given above. 72. A process’as claimed in claim 71,’wherein the acid acceptor used for the reaction with the amine of the general formula III is an excess of the amine of the general formula III, an inorganic base or a tertiary organic 10. base. 73. A process as Glaimed in claim 72, wherein the inorganic base is a sodium hydroxide solution, sodium carbonate or potassium carbonate. 74. A process as claimed in claim 72, wherein the tertiary organic base is triethylamine. 1g. 75. A process as claimed in claim 71, wherein the tertiary organic base used for the reaction of the free compound of the general formula IV is triethylamine or pyridine. 76. A process as claimed in claim 71, wherein the catalyst used for the reaction with the isocyanate of the general formula VI is an organic base. - 50 44673 77. A process as claimed in claim 71, wherein the catalytic hydrogenation is carried out by means of nickel in methanol. 78. A process as claimed in claim 71 or 77 wherein the acid acceptor used for the reaction with the compound of the general formula VIII is an inorganic base or a tertiary organic base. 5. (b) a compound of the general formula IV OH in which R 3 and X have the meanings given above, is reacted in the presence of a tertiary organic base or is reacted in the form of an alkali salt thereof with a carbamoyl chloride of the general formula V N-CO-C1 (V), in which R 1 and R 2 have the meanings given above, each reaction being carried 10. out at a temperature within the range of from 0° to 100°C, or, when represents a hydrogen atom, is reacted in the presence of a catalyst with an isocyanate of the general formula VI Rg-N-C-O in which R 2 has the meaning given above , or (c) a nitro compound of the general formula VII / R 1 O-CO-I^ (VI), -NO (VII), - 49 4 4673 in which R^ and Rg have the meanings given above (provided that they do not represent'groups that are capable of being easily hydrogenated), is catalytically hydrogenated to form the corresponding amine which is then reacted in the presence of an acid acceptor with a compound of the 5, 67. A pack which comprises the compound claimed in any one of claims 9 to 24 together with instructions for its use as a herbicide. 68. A pack which comprises the compound claimed in any one of claims 25 to 29. together with instructions for its use as a herbicide. 69. A pack which comprises a compound as claimed in claim 30 together 10. with instructions for its use as a herbicide. 70. A pack which comprises a compound as claimed in claim 31 together with instructions for its use as a herbicide. 71. A process for the manufacture of a compound, of the general formula I given in claim 1, in which R^ Rg R 3 and X have the meanings given in 15. claim 1, wherein (a) a compound of the general formula II (II) - 48 4 4 6 7 3 in which R 3 and X have the meanings given above, is reacted in the presence of an acid acceptor with an amine of the general formula III y/R-l Z (III). \ R R 2 in which R^ and R? have the meanings given above, or 5. 59. A method as claimed in claim 54, wherein the crop area is treated with a compound as claimed in claim 31. 60. A method as claimed in claim 54, wherein the crop area is treated with a herbicidal preparation as claimed in any one of the claims 32 to 43. 61. A method as claimed in any one of claims 54 to 60, wherein a single 10. compound of the general formula I is used for the treatment in an amount of approximately 0.5 to 5 kg per hectare. 62. A method as claimed in any one of claims 54 to 60, wherein two or more compounds of the general formula I are used for the treatment in a total amount of approximately 0.5 to 5 kg per hectare. 15. 63. A method as claimed in any one of claims 54 to 62, wherein the crop is a cereal crop or a potato crop. 64. A method as claimed in any one of claims 54 to 62, wherein the crop is a maize, wheat, barley or rice crop. - 47 - 44673 65. A pack which comprises a compound as claimed in claim 1 together with instructions fpr its use as a herbicide. 66. A pack which comprises a compound as claimed in any one of claims 2 to 8 together with instructions for its use as a herbicide. 5. 50. A method as claimed in claim 44, wherein the area is treated with a herbicidal preparation as claimed in any one of claims 32 to 43. 51. A method as claimed in any one of claims 44 to 50, wherein a single compound of the general formula I is used for the treatment in an amount of approximately 0.5 to 5 kg per hectare. 10. 52. A method as claimed in any one of claims 44 to 50, wherein two or more compounds of the general formula I are used for the treatment in a total amount of approximately.0.5 to 5 kg per hectare. 53. A method as claimed in claim 44, conducted substantially as described in example 2 herein. 15. 54. A method of protecting a crop area against weeds, wherein a crop area is treated with a compound of the general formula I given in claim 1, in which R-j» Rg, an ^ X have the meanings given in claim 1. 55. A method as claimed in claim 54, wherein the crop area is treated with a compound as claimed in any one of claims 2 to 8. 20. 56. A method as claimed in claim 54, wherein the crop area is treated with the compound claimed in any one of claims 9 to 24. - 46 4 4 6 7 3 57. A method as claimed in claim 54, wherein the crop area is treated with the compound claimed in any one of claims 25 to 29. 58. A method as claimed in claim 54, wherein the crop area is treated with a compound as claimed in claim 30. 5 containing two or more compounds of the general formula I in a total amount of approximately 10 to 80% by weight. 41. A preparation as claimed in any one of claims 32 to 40 containing a single surface-active agent in an amount of up to 20% by weight. 42. A preparation as claimed in any one of claims 32 to 40, containing 10 two or more surface-active agents in a total amount of up to 20% by weight. 43. Any one of the herbicidal preparations as claimed in claim 32 and substantially as described in Example 2 herein. 44. A method of protecting a living plant against weeds, wherein the area in the vicinity of a living plant is treated with a compound of the 15 general formula 1 given in claim 1, in which Rp Rg, Rg and X have the meanings given in claim 1. 45. A method as claimed in claim 44 wherein the area is treated with a compound as claimed in any one of claims 2 to 8. 46. A method as claimed in claim 44, wherein the area is treated with the 20 compound claimed in any one of claims 9 to 24. 47. A method as claimed in claim 44, wherein the area is treated with the compound claimed in any of claims 25 to 29. - 45 4 467 3 48. A method as claimed in claim 44, wherein the area is treated with a compound as claimed in claim 30. 49. A method as claimed in claim 44, wherein the area is treated with a compound as claimed in claim 31. 5. 14. Fi - (2 - Chlorethyl) - carbanilic acid(3 - (ethoxycarbonylaraino) phenyl) ester 15. K - (2 - Chlorethyl) - carbanilic acid (3-(methylthiocarbonylamino)phenyll ester 16. Fi « (2 - Chlorethyl) - carbanilic acid (3 - (ethylthiocarbonylamino) 10- phenyl]ester .. . 17. it - (2 - Bromethyl) - carbanilic acid (3 - (allyloxycarbonylamino) phenyl] ester 18. Fi - (2 - Chlorethyl) - carbanilic acid )3 - (1 - methylpropynyloxycarbonylamino) - phenyl] ester IS· 19. Fi - (2 - Bromethyl) - carbanilic acid {3 - (2 - propynyloxycarbonylamino)phenylj ester. 20. Fi - (2 - Chlorethyl) - carbanilic acid (3-(2- propynyloxycarbonylamino) phenyl] ester. - 42 4 4673 21. Ν - (2 - Bromethyl) - 2 - methylcarbanilic acid(3 -(methoxycarbonylamino) - pheny| ester. 22. N - (2 - Bromethyl) - 3 - chlorocarbanilic acid(3 -(methoxycarbonylamino) - phenyl] ester 23. N - (2 - Bromethyl) - 2 - methylcarbanilic acid[3 - (ethoxycarbonylamino) - phenyl] ester. 24. N - (2 - Bromethyl) - 3 - chlorocarbanilic acid (3 -(1- methyl ethoxycarbonyl ami no) - phenyl ester. 25. N - (2 - Bromethyl) - carbanilic acid -(2- methyl propoxycarbonylamino)-phenyl] ester. 26. N - (2 - Bromethyl) - 3 - chlorocarbanilic acid [3 -(2 - methyl propoxycarbonyl ami no) - phenyl] ester. 27. N - (2 - Chlorethyl) - 3 - methoxycarbanilic acid[3 -(methoxycarbonylamino) - phenyl] ester. 28. N - (2 - Chlorethyl) - 3 - tri fluoromethylcarbanilic acid β -(methoxycarbonylamino) - phenylj ester. 29. N - (2 - Bromethyl) - 3 - tri fluoromethyl carbanilic acid (3 -(methoxycarbonylamino) - phenyl] ester. - 43 446.7.31. 30. Any one of the compounds numbered as 17 to 54 in Table 1 herein. 31. Any one of the compounds numbered as 55 to 62, 65 to 76 and 78 to 87 in Table I herein. 32. A herbicidal preparation which comprises a compound of the general formula 1 given in claim .1, in which R-j, Rg. Rg and X have the meanings given.in claim I in admixture or conjunction with a suitable carrier. 33. A herbicidal preparation which comprises a compound claimed in any one of claims 2 to 8, in admixture or conjunction with a suitable carrier. 34. A herbicidal preparation which comprises the compound claimed in any 10. one of claims 9 to 24 in admixture or conjunction with a suitable carrier. 35. A herbicidal preparation which comprises the.compound claimed in any one of claims 25 to 29, in admixture or conjunction with a suitable carrier. - ' . 36. A herbicidal preparation which comprises a compound as claimed in claim 15. 30 in admixture or conjunction with a suitable carrier. 37. A herbicidalpreparation which comprises a compound as claimed in claim 31, in admixture or conjunction with a suitable carrier. 38. A preparation as claimed in any one of claims 32 to 3? which is in the form of a powder, a strewable preparation granules, a solution, an emulsion 20. ora suspension, -44- - . 4 46γ 3 39. A preparation as claimed in any one of claims 32 to 38 containing a single compound of the general formula I in an amount of approximately 10 to 80% by weight. 40. A preparation as claimed in any one of claims 32 to 38 5. 5. A compound as claimed in any one of claims 1 to 4, wherein the alkyl, alkenyl or alkynyl group represented by Rg contains up to 4 carbon atoms.

5. or methoxyphenyl group, and R 3 represents an alkyl, alkenyl or alkynyl group, or R.| represents a hydrogen atom or an alkyl, alkenyl, alkynyl or halogenoalkyl group. TO. R 2 represents an alkyl, halogenoalkyl, alkenyl, cycloalkyl, alkynylcycloalkyl, benzyl, phenylethyl, phenyl, methyl phenyl,ethyl phenyl, halogenophenyl, trifluoromethylphenyl or methoxyphenyl group, and R 3 represents a methoxyethyl group, and X represents an oxygen or sulphur atom. 15.

6. A compound as claimed in claim 1 or 4, wherein the alkyl, alkenyl or alkynyl group represented by R^ contains up to 5 carbon atoms.

7. A compound as claimed in any one of claims 1 to 3 and 6, wherein the halogenalkyl group represented by Rg is a bromalkyl or chloralkyl group. 10.

8. A compound as claimed in any one of claims 1 to 3 and 6, wherein the alkyl or alkenyl group represented by Rg contains up to 4 carbon atoms.

9. N - (2 -Bromethyl) - carbanilic acid ^-(methoxycarbonylanrino)-phenyl) ester. 10. N - (2 - Bromethyl) - carbanilic acid (3-(ethoxy carbonyl ami no )15. pheny Ijester 11. N - ( 2 - Bromethyl) - carbanilic acid (3 -(methylthiocarbonylamino) phenyl) ester, 41 446^ 3 12. N - ( 2 - Bromethyl) - carbanilic acid (3 - (ethylthiocarbonylamino)phenyl) ester 13. M - ( 2 -Chlorethyl) - carbanilic acid(3 - (methoxycarbonylamino)phenyl] ester :

10. , 81. A process as claimed in claim 71, conducted substantially as described in Example 1 herein.