Azo compounds having a 5-substituted-4-chlorothiazolyl-2-diazo component radical

A compound of the formula ##STR29## wherein K is the radical of a coupling component, said coupling component being 1-phenyl-3-methyl-5-aminopyrazole, 1-phenyl-3-methylpyrazolone-5,3-methylpyrazolone-5,1-(2'-hydroxyethyl)-3-m ethylpyrazolone-5,1-n-butyl-3-cyano-4-methyl-6-hydroxypyridone-2,1-methyl-2 -phenylindole, 2-hydroxydiphenyl, p-cresol, 2-hydroxynaphthalene-3-carboxylic acid ethyl ester, 2-diethylamino-b 4-phenyl-1,3-thiazole, 2-benzylamino-3-cyano-4-methyl-6-(2'-hydroxyethyl)pyridine, 2,6-di-(n-butylamino)-3-cyano-4-methylpyridine, 2,6-di(3'-methoxypropylamino)-3-cyano-4-methylpyridine, 2-benzylamino-3-cyano-4,6-di-(methylamino)pyridine, 2,4,6-tri-(3'-methoxypropylamino)-3-cyanopyridine, 1-(N-cyanoethyl)naphthylamine or N-(3'-methoxypropylamino)-4-hydroxynaphthalimide, ##STR30## wherein R.sub.5 is hydrogen;

• C.sub.1-2 alkyl;
• C.sub.1-2 alkoxy;
• cyano;
• formamido;
• (C.sub.1-4 alkyl)carbonylamino;
• (C.sub.1-4 alkyl)carbonylamino the alkyl moiety of which is monosubstituted by hydroxy, chloro, bromo, C.sub.1-4 alkoxy, phenyl, phenoxy, benzloxy or (C.sub.1-2 alkoxy)carbonyl;
• benzamido;
• acryloylamino;
• allylcarbonylamino;
• aminocarbonylamino;
• (C.sub.1-4 alkyl)aminocarbonylamino;
• (C.sub.1-4 alkoxy)carbonylamino;
• (C.sub.1-4 alkoxy)carbonylamino the alkoxy moiety of which is monosubstituted by C.sub.1-2 alkoxy or phenyl;
• C.sub.1-2 alkylsulfonylamino;
• phenylsulfonylamino;
• di-(C.sub.1-2 alkyl)aminosulfonylamino;
• chloro or bromo,
• R.sub.6 is hydrogen, chloro, bromo, C.sub.1-2 alkyl, C.sub.1-2 alkoxy or (C.sub.1-2 alkoxy)ethoxy, with the proviso that not more than one of R.sub.5 and R.sub.6 is chloro or bromo,
• R.sub.7 is hydrogen;
• C.sub.1-8 alkyl;
• C.sub.1-4 alkyl substituted by 1 or 2 substituents each of which is independently chloro, bromo, hydroxy, thiocyano, cyano, (C.sub.1-4 alkyl)carbonyl, (C.sub.1-4 alkoxy)carbonyl, formyloxy, (C.sub.1-10 alkyl)carbonyloxy, cyclohexyl, (C.sub.1-3 chloroalkyl)carbonyloxy, (C.sub.1-3 bromoalkyl)carbonyloxy, (C.sub.1-10 alkoxy)carbonyloxy, (C.sub.1-2 alkoxy)ethoxycarbonyloxy, (C.sub.3-4 alkenyl)oxycarbonyl, chloroallyloxycarbonyl, bromoallyloxycarbonyl, C.sub.3-4 alkenyloxy, chloroallyloxy, bromoallyloxy, propynyloxy, benzoyloxy, C.sub.1-4 alkoxy, phenyl, phenoxy or phenyl(C.sub.1-4 alkoxy), with the proviso that not more than one substituent is a member of the group consisting of benzoyloxy, phenyl, phenoxy and and phenyl(C.sub.1-4 alkoxy);
• (C.sub.1-4 alkoxy)C.sub.1-4 alkyl the alkoxy moiety of which is monosubstituted by chloro, bromo, cyano, C.sub.1-4 alkoxy, (C.sub.1-4 alkoxy)carbonyl, (C.sub.1-4 alkoxy)carbonyloxy or (C.sub.1-4 alkyl)carbonyloxy;
• C.sub.3-4 alkenyl;
• C.sub.3-4 alkenyl monosubstituted by phenyl, chloro or bromo;
• propynyl;
• C.sub.5-7 cycloalkyl;
• cyclohexyl substituted by 1, 2 or 3 methyl groups;
• phenyl or phenyl substituted by 1, 2 or 3 substituents each of which is independently chloro, bromo, methyl or C.sub.1-2 alkoxy,
• R.sub.8 is hydrogen;
• C.sub.1-8 alkyl;
• C.sub.1-4 alkyl monosubstituted by chloro, bromo, hydroxy, cyano, thiocyano, (C.sub.1-4 alkyl)carbonyl, (C.sub.1-4 alkoxy)carbonyl, formyloxy, (C.sub.1-4 alkyl)carbonyloxy, (C.sub.1-4 chloroalkyl)carbonyloxy, (C.sub.1-4 bromoalkyl)carbonyloxy, (C.sub.1-4 alkoxy)carbonyloxy, (C.sub.1-2 alkoxy)ethoxycarbonyloxy, (C.sub.3-4 alkenyl)oxycarbonyl, chloroallyloxycarbonyl, bromoallyloxycarbonyl, C.sub.3-4 alkenyloxy, chloroallyloxy, bromoallyloxy, propynyloxy, benzoyloxy, C.sub.1-4 alkoxy, phenyl, phenoxy, phenyl(C.sub.1-4 alkoxy), carbamoyl, (C.sub.1-4 alkyl)carbamoyl, di-(C.sub.1-4 alkyl)carbamoyl, (C.sub.1-4 alkyl)carbamoyloxy, di-(C.sub.1-4 alkyl)carbamoyloxy, phenylcarbamoyl, phenylcarbamoyloxy, phthalimidyl-2, succinimidyl-2, saccharinyl-2, pyridyl or benzothiazolyl-2-mercapto;
• (C.sub.1-4 alkoxy)C.sub.1-4 alkyl the alkoxy moiety of which is monosubstituted by chloro, bromo, cyano, C.sub.1-4 alkoxy, (C.sub.1-4 alkoxy)carbonyl, (C.sub.1-4 alkoxy)carbonyloxy or (C.sub.1-4 alkyl)carbonyloxy;
• 2-hydroxy, (C.sub.1-4 alkyl)carbonyloxy or (C.sub.3-4 alkenyl)carbonyloxy-3-allyloxypropyl;
• 2-hydroxy, (C.sub.1-4 alkyl)carbonyloxy or (C.sub.3-4 alkenyl)carbonyloxy-3-propynyloxypropyl;
• C.sub.3-4 alkenyl or C.sub.3-4 alkenyl monosubstituted by chloro, bromo or phenyl, or
• R.sub.7 and R.sub.8 taken together and with the nitrogen atom to which they are joined are piperidino or morpholino,
• R.sub.x is hydroxyethyl, methyl, ethyl, methoxycarbonylethyl, ethoxycarbonylethyl, benzyl, methoxyethyl, ethoxyethyl or acetoxyethyl,
• and
• R.sub.y is hydrogen, methyl or acetamido,
• R is --CHO, --CH.dbd.C(CN)--R.sub.1, --CH.dbd.CH--R.sub.2, --CH.dbd.C(NO.sub.2)--R.sub.3, --CH.dbd.NOH or --CN,
• wherein
• R.sub.1 is (C.sub.1-10 alkoxy)carbonyl;
• (C.sub.1-10 alkoxy)carbonyl monosubstituted by chloro, bromo, cyano, hydroxy, C.sub.1-2 alkoxy, (C.sub.1-2 alkyl)carbonyloxy or (C.sub.1-2 alkoxy)carbonyl;
• (C.sub.1-10 alkoxy)carbonyl disubstituted by hydroxy and by chloro or bromo;
• (C.sub.3-8 alkenyl)oxycarbonyl;
• (C.sub.3-8 chloroalkenyl)oxycarbonyl;
• (C.sub.3-8 bromoalkenyl)oxycarbonyl;
• propynyloxycarbonyl;
• benzyloxycarbonyl;
• chlorobenzyloxycarbonyl;
• nitrobenzyloxycarbonyl;
• C.sub.1-4 alkylsulfonyl;
• phenylsulfonyl;
• tolylsulfonyl;
• carbamoyl;
• (C.sub.1-2 alkyl)carbamoyl;
• di-(C.sub.1-2 alkyl)carbamoyl;
• phenylcarbamoyl;
• aminothiocarbonyl;
• benzimidazolyl-2;
• cyano;
• acetyl;
• phenyl;
• benzoyl or phenyl or benzoyl substituted by 1, 2 or 3 substituents each of which is independently chloro, bromo or nitro, with the proviso that the maximum number of nitro groups is two, and
• R.sub.2 is phenyl;
• benzoyl or phenyl or benzoyl substituted by 1, 2 or 3 substituents each of which is independently chloro, bromo or nitro, with the proviso that the maximum number of nitro groups is two, and
• R.sub.3 is hydrogen, methyl or ethyl, and
• m is 0 or 1,
• with the provisos that (i) when R is --CN, m must be 1, and (ii) the molecule is free of ##STR31## radicals.