Monoazo and disazo compounds having optionally further substituted 2-acyl-, carboxy- or cyano-benzothienyl diazo component radicals

Claim 1

A compound of the formula ##STR35## wherein each R 1 is independently halo, C 1-8 alkyl, substituted C 1-8 alkyl, C 5-8 cycloalkyl, substituted C 5-8 cycloalkyl, C 1-8 alkoxy, substituted C 1-8 alkoxy, C 5-8 cycloalkyloxy, substituted C 5-8 cycloalkyloxy, trifluoromethyl or nitro, R 2 is carboxy, carbamoyl, (C 1-8 alkyl)carbamoyl, (substituted C 1-8 alkyl)carbamoyl, (C 5-8 cycloalkyl)carbamoyl, (substituted C 5-8 cycloalkyl)carbamoyl, di-(C 1-8 alkyl)carbamoyl, di-(substituted C 1-8 alkyl)carbamoyl, N-C 1-8 alkyl-N-(substituted C 1-8 alkyl)carbamoyl, phenylcarbamoyl, substituted phenylcarbamoyl, (C 1-8 alkoxy)carbonyl, (substituted C 1-8 alkoxy)carbonyl, (C 5-8 cycloalkyloxy)carbonyl, (substituted C 5-8 cycloalkyloxy)carbonyl, phenoxycarbonyl, substituted phenoxycarbonyl or cyano, ##STR36## when m is 2, wherein R 5 is phenyl; phenyl substituted by 1-3 substituents each of which is independently chloro, bromo, methyl, methoxy or trifluoromethyl or benzimidazolonyl-5, R 6 is hydroxy or amino, R 7 is hydrogen, methyl, phenyl, methoxycarbonyl or ethoxycarbonyl, R 8 is hydrogen, methyl, ethyl, phenyl or phenyl substituted by 1-3 substituents each of which is independently chloro, bromo, cyano, nitro, methyl, methoxy or ethoxy, R 9 is hydrogen; methyl; formamido; (C 1-4 alkyl)carbonylamino; (C 1-4 alkyl)carbonylamino monosubstituted by chloro, bromo, phenyl, C 1-4 alkoxy or phenoxy; (C 1-4 alkoxy)carbonylamino; (C 1-4 alkoxy)carbonylamino monosubstituted by chloro, bromo, phenyl, C 1-4 alkoxy or phenoxy; C 1-4 alkylsulfonylamino or C 1-4 alkylsulfonylamino monosubstituted by chloro, bromo, phenyl, C 1-4 alkoxy or phenoxy, R 10 is hydrogen, methoxy or ethoxy, R 11 is C 1-4 alkyl or C 1-4 alkyl or C 1-4 alkyl monosubstituted by chloro, bromo, cyano, hydroxy, methoxy, ethoxy, phenyl, phenoxy, (C 1-4 alkyl)carbonylamino, (C 1-4 alkyl)carbonyloxy, (C 1-4 alkoxy)carbonyl or (C 1-4 alkoxy)carbonyloxy, R 12 is hydrogen, C 1-4 alkyl or C 1-4 alkyl monosubstituted by chloro, bromo, cyano, hydroxy, methoxy, ethoxy, phenyl, phenoxy, (C 1-4 alkyl)carbonylamino, (C 1-4 alkyl)carbonyloxy, (C 1-4 alkoxy)carbonyl or (C 1-4 alkoxy)carbonyloxy, R 13 is hydrogen, phenyl, amino, C 1-4 alkylamino, di-(C 1-4 alkyl)amino, C 1-4 alkyl or C 1-4 alkyl monosubstituted by chloro, bromo, cyano, hydroxy, methoxy, ethoxy, phenyl, phenoxy, (C 1-4 alkyl)carbonylamino, (C 1-4 alkyl)carbonyloxy, (C 1-4 alkoxy)carbonyl or (C 1-4 alkoxy)carbonyloxy, and X is a direct bond, ##STR37##wherein R 14 is two hydrogen, --SO 2 --, --NH--, --O-- or --S, R 15 is --O--, --S--, --CH 2 --, --NH--, --CO-- or --SO 2 --, each R 16 is independently chloro, bromo, nitro, cyano, trifluoromethyl, methyl, methoxy, ethoxy, methoxycarbonyl or ethoxycarbonyl, and n is 0, 1 or 2, m is 1 or 2, and n is 0, 1 or 2, wherein each substituted C 1-8 alkyl and substituted C 1-8 alkoxy group and moiety independently has 1 or 2 substituents each of which is independently halo, cyano, hydroxy, C 1-4 alkoxy, phenyl, phenoxy, acyl, acyloxy or acylamino, each substituted C 5-8 cycloalkyl and substituted C 5-8 cycloalkyloxy group and moiety independently has 1 or 2 substituents each of which is independently C 1-4 alkyl, halo, cyano, hydroxy, C 1-4 alkoxy, phenyl, phenoxy, acyl, acyloxy or acylamino, each substituted phenyl and substituted phenoxy moiety independently has 1 or 2 substituents each of which is independently nitro, C 1-4 alkyl, halo, cyano, hydroxy, C 1-4 alkoxy, phenyl, phenoxy, acyl, acyloxy or acylamino, each acyl and acyl moiety of acyloxy and acylamino is independently R--Y-- or R'--Z--, wherein R is C 1-4 alkyl; C 1-4 alkyl substituted by 1 or 2 substituents each of which is independently halo, cyano, hydroxy, C 1-4 alkoxy, phenyl or phenoxy; phenyl or phenyl substituted by 1 or 2 substituents each of which is independently nitro, C 1-4 alkyl, halo, cyano, hydroxy, C 1-4 alkoxy, phenyl or phenoxy, Y is --O--CO--, --SO 2 -- or --OSO 2 --, Z is --CO--, --NR'--CO-- or --NR'--SO 2 --, and R' is hydrogen; C 1-4 alkyl; C 1-4 alkyl substituted by 1 or 2 substituents each of which is independently halo, cyano, hydroxy, C 1-4 alkoxy, phenyl or phenoxy; phenyl or phenyl substituted by 1 or 2 substituents each of which is independently nitro, C 1-4 alkyl, halo, cyano, hydroxy, C 1-4 alkoxy, phenyl or phenoxy, and each halo is independently fluoro; chloro or bromo.