Patent GB-1465451-A (GB)
Title: 3-amino-phenyl-acetic acid derivatives processes for their preparation and their use as herbicides
IPC: A01N47/30
Filed: 1975-04-25
Abstract: 1465451 3 - Amino - phenylacetic acid derivatives and their use as herbicides BAYER AG 25 April 1975 [15 May 1974 27 Feb 1975] 17287/75 Heading C2C 3 - Amino - phenylacetic acid derivatives of the formula in which X represents the group OR or SR in which R is alkyl with 1 to 6 carbon atoms optionally substituted by halogen, alkoxy, aryloxy optionally substituted by chlorine atoms in the aryl ring, alkylmercapto or arylmercapto, or R is alkenyl with 3 to 6 carbon atoms optionally substituted by halogen, alkoxy, aryloxy, alkylmercapto or arylmercapto, or R is alkynyl with 3 to 6 carbon atoms optionally substituted by halogen, alkoxy, aryloxy, alkylmercapto or arylmercapto, or R is optionally alkyl-substituted cycloalkyl with 4 to 6 carbon atoms in the cycloalkyl radical, or R is aralkyl with 1 to 4 carbon atoms in the alkyl moiety and 6 to 10 carbon atoms in the aryl moiety, the aryl moiety optionally being substituted by halogen, alkyl, haloalkyl, alkoxy, alkylmercapto and/or nitro, or X represents the group NR<SP>1</SP>R<SP>2</SP> in which R<SP>1</SP> is hydrogen, alkyl with 1 to 4 carbon atoms or alkenyl with 2 to 4 carbon atoms, and R<SP>2</SP> is alkyl with 1 to 15 carbon atoms, alkenyl with 3 to 12 carbon atoms or alkynyl with 3 to 12 carbon atoms, each of these alkyl, alkenyl and alkynyl radicals being optionally substituted by halogen, cyano, carboxylic acid ester groups, carboxylic acid amide groups, alkoxy, aryloxy, alkylmercapto, arylmercapto, alkylsulphonyl or arylsulphonyl, or by aryl optionally substituted by halogen, alkyl, haloalkyl, alkoxy, alkylmercapto and/or nitro, or by optionally substituted cycloalkyl with 3 to 6 carbon atoms and/or by 5-membered or 6-membered heterocyclic groups with 1 to 3 hetero-atoms in the ring, or R<SP>2</SP> is cycloalkyl with 3 to 8 carbon atoms in the ring, optionally substituted by alkyl, halogen or alkoxy, or R<SP>2</SP> is aryl with 6 to 10 carbon atoms optionally monosubstituted or polysubstituted by halogen, nitro, cyano, carboxylic acid ester or carboxylic acid amide, alkyl with 1 to 6 carbon atoms, cycloalkyl with 5 or 6 carbon atoms, alkoxy, haloalkoxy, aryloxy, alkylmercapto, arylmercapto, alkylsulphonyl, arylsulphonyl, haloalkyl and/or thiocyano, or R<SP>2</SP> is an optionally substituted 5- membered or 6-membered heterocyclic radical with 1 to 3 hetero-atoms in the ring, with further rings optionally being fused to the heterocyclic ring, or R<SP>1</SP> and R<SP>2</SP> together with the adjoining nitrogen atom form an optionally substituted 5- membered to 8-membered heterocyclic ring in which 1 to 3 carbon atoms can be replaced by oxygen, nitrogen, sulphur, SO 2  or N-alkyl, and which can be fused to other carbocyclic or heterocyclic ring systems, Y is oxygen or sulphur, and Z is alkyl with 1 to 12 carbon atoms, alkenyl with 2 to 12 carbon atoms or alkynyl with 2 to 6 carbon atoms, each of these alkyl, alkenyl and alkynyl radicals being optionally monosubstituted or polysubstituted by halogen, alkoxy, optionally substituted aryloxy, alkylmercapto, optionally substituted arylmercapto and/or optionally halogen-substituted or alkyl-substituted aryl with 6 to 10 carbon atoms, or Z is cycloalkyl with 3 to 6 carbon atoms or is aryl optionally monosubstituted or polysubstituted by halogen, alkyl, haloalkyl, nitro and/or alkoxy, or Z represents the group OR<SP>3</SP> or SR<SP>3</SP>, in which R<SP>3</SP> is alkyl with 1 to 6 carbon atoms or alkenyl with 2 to 6 carbon atoms, each of these alkyl or alkenyl radicals being optionally substituted by halogen, alkoxy, optionally substituted aryloxy and/or aryl which is optionally substituted by halogen, nitro, alkyl and/or alkoxy, or R<SP>3</SP> is optionally substituted alkynyl with 3 to 6 carbon atoms, or Z represents the group NR<SP>4</SP>R<SP>5</SP> in which R<SP>4</SP> is hydrogen, alkyl with 1 to 4 carbon atoms or alkenyl with 2 to 4 carbon atoms, and R<SP>5</SP> is alkyl with 1 to 4 carbon atoms which is optionally substituted by halogen or alkoxy, alkenyl with 2 to 4 carbon atoms, alkynyl with 3 to 6 carbon atoms or optionally alkyl-substituted cycloalkyl with 5 or 6 carbon atoms, or R<SP>4</SP> and R<SP>5</SP> together with the adjoining nitrogen atom form an optionally substituted 5-membered to 8-membered heterocyclic ring in which 1 to 3 carbon atoms can be replaced by oxygen, nitrogen, sulphur, SO 2  or N-alkyl. These compounds may be obtained by any one of the following processes: (A) by reacting a compound of formula in which X has the same meaning as above with either a compound of formula in which Y and Z have the meanings as given above and Q represents halogen or the group OR<SP>3</SP> or -O-CO-R<SP>3</SP> in which R<SP>3</SP> has the same meaning as given above, or with an isocyanate or isothiocyanate of formula in which R<SP>5</SP> and Y have the same meanings as given above, optionally in the presence of a diluent and optionally in the presence of an acid binding agent; (B) by reacting a compound of formula in which Y and Z have the same meanings as given above and W represents CN or the group R<SP>6</SP>CO- in which R<SP>6</SP> is hydroxyl, halogen, alkoxy, haloalkoxy or aryloxy which is optionally substituted by halogen, alkyl, and/or nitro with an alcohol, mercaptan, or amine of formula in which X has the same meaning as given above, or with an alkali metal salt of such an alcohol or mercaptan optionally in the presence of a diluent and optionally in the presence of an acid binding agent and optionally in the presence of a catalyst; (C) by reacting a 3-isocyanato or 3-isothiocyanato-phenylacetic acid of formula in which Y has the same meaning as given above and Hal is halogen, with an alcohol, mercaptan or amine of formula in which X has the same meaning as given above, optionally in the presence of a diluent and optionally in the presence of an acid-binding agent; (D) by reacting a 3-isocyanato- or 3- isothiocyanato-phenylacetic acid derivative of formula in which X and Y have the same meanings as given above, with an alcohol or mercaptan of formula in which R<SP>3</SP> has the same meaning as given above, or with an amine of formula in which R<SP>4</SP> and R<SP>5</SP> have the same meanings as given above, optionally in the presence of a diluent and optionally in the presence of a catalyst. The Specification also describes the preparation of the following intermediates. 3 - Aminophenylacetic acid isopropylamide by the reduction of 3-nitrophenyl acetic acid isopropyl amide with H/C 2 H 5 OH. Other similar compounds of Formula II shown above, in which X represents -NHCH 3 , -NHC 2 H 5 , -NH-n-C 3 H 7 , -NH-n-C 4 H 9 , -NH - cyclohexyl, -NH - phenyl, -NH- (3 - methylphenyl), -NH - (4 - methylphenyl), -NH - (3 - chloro phenyl), -NH- (4 - chloro phenyl), methyl - 2 - tetrahydropyran amino, -NH-CH 2 -(2-tetrabydro-pyran), -OCH 3 , or -OCH(CH 3 ) 2  are also prepared. 3 - Nitro - phenylacetic acid isopropylamide by treating 3-nitrophenylacetic acid chloride with isopropylamine. In the same manner compounds of formula in which X represents -NHCH 3 , -NHC 2 H 5 , -NH-n-C 3 H 7 , -NH-n-C 4 H 9 , -N(CH 3 ) 2 , -N(C 2 H 5 ) 2 , -NH-cyclohexane, -NH - phenyl, -NH - (3 - methylphenyl), -NH - (4 - methylphenyl), -NH - (3 - chlorophenyl), -NH-(4-chlorophenyl), -NH-CH 2 - (2 - tetrahydro - pyran) or 1,2,4 - triazole are also prepared. The invention also comprises a herbicidal composition which contains as an active ingredient a compound according to the invention in admixture with a solid or liquid diluent.