Asymmetric dioxazine compounds having a triazinyl bridging group and a method of production and use thereof

A compound represented by the following formula in the free acid form, ##STR417## wherein R.sub.1, R.sub.2 and R.sub.3 independently of one another are each hydrogen or C.sub.1 to C.sub.4 alkyl which is unsubstituted or substituted by hydroxy, cyano, C.sub.1 to C.sub.4 alkoxy, halogen, carbamoyl, carboxy, C.sub.1 to C.sub.4 alkoxycarbonyl, C.sub.1 to C.sub.4 alkylcarbonyloxy, sulfo or sulfamoyl;

• X.sub.1 and X.sub.2 independently of one another are each hydrogen, halogen, alkyl, alkoxy or phenoxy;
• Y is --CH.sub.2).sub.2, --CH.sub.2).sub.3, --CH.sub.2).sub.2 O--CH.sub.2).sub.2, phenylene which is unsubstituted or substituted once or twice by methyl, ethyl, methoxy, ethoxy, chlorine, bromine, nitro, carboxy or sulfo, or naphthylene which is unsubstituted or substituted once by sulfo;
• Z is --SO.sub.2 CH.dbd.CH.sub.2 or --SO.sub.2 CH.sub.2 CH.sub.2 Z' in which Z' is a group capable of being split by the action of an alkali;
• Q.sub.1 and Q.sub.2 independently of one another are each amino which is unsubstituted or substituted by alkyl, cycloalkyl, aralkyl, aryl or a heterocyclic ring selected from the group consisting of furan, thiophene, pyrazole, pyridine, pyrimidine, quinoline, benzimidazole, benzothiazole and benzoxazole, or an N-heterocyclic ring-constituting amino selected from the group consisting of morpholino, piperidino and piperazino, said alkyl, cycloalkyl, aralkyl, aryl, heterocyclic ring and N-heterocyclic ring-constituting amino each being unsubstituted or substituted by halogen, nitro, cyano, trifluoromethyl, sulfamoyl, carbamoyl, C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, ureido, hydroxy, carboxy, sulfomethyl or sulfo;
• and
• Q.sub.3 is amino which is unsubstituted or substituted by alkyl, cycloalkyl, aralkyl, aryl or a heterocyclic ring selected from the group consisting of furan, thiophene, pyrazole, pyridine, pyrimidine, quinoline, benzimidazole, benzothiazole and benzoxazole, or an N-heterocyclic ring-constituting amino selected from the group consisting of morpholino, piperidino and piperazino, said alkyl, cycloalkyl, aralkyl, aryl, heterocyclic ring and N-heterocyclic ring-constituting amino each being unsubstituted or substituted by halogen, nitro, cyano, trifluoromethyl, sulfamoyl, carbamoyl, C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, ureido, hydroxy, carboxy, sulfomethyl or sulfo or a group of formula (3), ##STR418## in which R.sub.5 is hydrogen or C.sub.1 to C.sub.4 alkyl which is unsubstituted or substituted by hydroxy, cyano, C.sub.1 to C.sub.4 alkoxy, halogen, carbamoyl, carboxy, C.sub.1 to C.sub.4 alkoxycarbonyl, C.sub.1 to C.sub.4 alkylcarbonyloxy, sulfo or sulfamoyl, Y.sub.1 is --CH.sub.2).sub.2, --CH.sub.2).sub.3, --CH.sub.2).sub.2 O--CH.sub.2).sub.2, phenylene which is unsubstituted or substituted once or twice by methyl, ethyl, methoxy, ethoxy, chlorine, bromine, nitro, carboxy or sulfo, or naphthylene which is unsubstituted or substituted once by sulfo, and Z.sub.1 is --SO.sub.2 CH.dbd.CH.sub.2 or --SO.sub.2 CH.sub.2 CH.sub.2 Z" in which Z" is a group capable of being split by the action of an alkali.

A compound represented by the following formula in the free acid form, ##STR419## wherein R.sub.1, R.sub.2 and R.sub.3 independently of one another are each hydrogen or C.sub.1 to C.sub.4 alkyl which is unsubstituted or substituted by hydroxy, cyano, C.sub.1 to C.sub.4 alkoxy, halogen, carbamoyl, carboxy, C.sub.1 to C.sub.4 alkoxycarbonyl, C.sub.1 to C.sub.4 alkylcarbonyloxy, sulfo or sulfamoyl;

• X.sub.1 and X.sub.2 independently of one another are each hydrogen, halogen, alkyl, alkoxy or phenoxy;
• Y is --CH.sub.2).sub.2, --CH.sub.2).sub.3, --CH.sub.2).sub.2 O--CH.sub.2).sub.2, phenylene which is unsubstituted or substituted once or twice by methyl, ethyl, methoxy, ethoxy, chlorine, bromine, nitro, carboxy or sulfo, or naphthylene which is unsubstituted or substituted once by sulfo;
• Z is --SO.sub.2 CH.dbd.CH.sub.2 or --SO.sub.2 CH.sub.2 CH.sub.2 Z' in which Z' is a group capable of being split by the action of an alkali;
• W is carbonyl or sulfonyl;
• R.sub.4 is alkyl which is unsubstituted or substituted by carboxy or sulfo, or phenyl which is unsubstituted or substituted by carboxy or sulfo;
• and
• Q.sub.3 is amino which is unsubstituted or substituted by alkyl, cycloalkyl, aralkyl, aryl or a heterocyclic ring selected from the group consisting of furan, thiophene, pyrazole, pyridine, pyrimidine, quinoline, benzimidazole, benzothiazole and benzoxazole, or an N-heterocyclic ring-constituting amino selected from the group consisting of morpholino, piperidino and piperazino, said alkyl, cycloalkyl, aralkyl, aryl, heterocyclic ring and N-heterocyclic ring-constituting amino each being unsubstituted or substituted by halogen, nitro, cyano, trifluoromethyl, sulfamoyl, carbamoyl, C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, ureido, hydroxy, carboxy, sulfomethyl or sulfo, or a group of formula (3), ##STR420## in which R.sub.5 is hydrogen or C.sub.1 to C.sub.4 alkyl which is unsubstituted or substituted by hydroxy, cyano, C.sub.1 to C.sub.4 alkoxy, halogen, carbamoyl, carboxy, C.sub.1 to C.sub.4 alkoxycarbonyl, C.sub.1 to C.sub.4 alkylcarbonyloxy, sulfo or sulfamoyl, Y.sub.1 is --CH.sub.2).sub.2, --CH.sub.2).sub.3, --CH.sub.2).sub.2 O--CH.sub.2).sub.2, phenylene which is unsubstituted or substituted once or twice by methyl, ethyl, methoxy, ethoxy, chlorine, bromine, nitro, carboxy or sulfo, or naphthylene which is unsubstituted or substituted once by sulfo, and Z.sub.1 is --SO.sub.2 CH.dbd.CH.sub.2 or --SO.sub.2 CH.sub.2 CH.sub.2 Z" in which Z" is a group capable of being split by the action of an alkali.

A compound represented by the following formula in the free acid form, ##STR421## wherein R.sub.1, R.sub.2 and R.sub.3 independently of one another are each hydrogen or C.sub.1 to C.sub.4 alkyl which is unsubstituted or substituted by hydroxy, cyano, C.sub.1 to C.sub.4 alkoxy, halogen, carbamoyl, carboxy, C.sub.1 to C.sub.4 alkoxycarbonyl, C.sub.1 to C.sub.4 alkylcarbonyloxy, sulfo or sulfamoyl;

• X.sub.1 and X.sub.2 independently of one another are each hydrogen, halogen, alkyl, alkoxy or phenoxy;
• Y is --CH.sub.2).sub.2, --CH.sub.2).sub.3, --CH.sub.2).sub.2 O--CH.sub.2).sub.2, phenylene which is unsubstituted or substituted once or twice by methyl, ethyl, methoxy, ethoxy, chlorine, bromine, nitro, carboxy or sulfo, or naphthylene which is unsubstituted or substituted once by sulfo;
• Z is --SO.sub.2 CH.dbd.CH.sub.2 or --SO.sub.2 CH.sub.2 CH.sub.2 Z' in which Z' is a group capable of being split by the action of an alkali;
• Q is halogen, alkoxy, amino which is unsubstituted or substituted by alkyl, cycloalkyl, aralkyl, aryl or a heterocyclic ring selected from the group consisting of furan, thiophene, pyrazole, pyridine, pyrimidine, quinoline, benzimidazole, benzothiazole and benzoxazole, or an N-heterocyclic ring-constituting amino selected from the group consisting of morpholino, piperidino and piperazino, said alkyl, cycloalkyl, aralkyl, aryl, heterocyclic ring and N-heterocyclic ring-constituting amino each being unsubstituted or substituted by halogen, nitro, cyano, trifluoromethyl, sulfamoyl, carbamoyl, C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, ureido, hydroxy, carboxy, sulfomethyl or sulfo, or a group of formula (3), ##STR422## in which R.sub.5 is hydrogen or C.sub.1 to C.sub.4 alkyl which is unsubstituted or substituted by hydroxy, cyano, C.sub.1 to C.sub.4 alkoxy, halogen, carbamoyl, carboxy, C.sub.1 to C.sub.4 alkoxycarbonyl, C.sub.1 to C.sub.4 alkylcarbonyloxy, sulfo or sulfamoyl, Y.sub.1 is --CH.sub.2).sub.2, --CH.sub.2).sub.3, --CH.sub.2).sub.2 O--CH.sub.2).sub.2, phenylene which is unsubstituted or substituted once or twice by methyl, ethyl, methoxy, ethoxy, chlorine, bromine, nitro, carboxy or sulfo, or naphthylene which is unsubstituted or substituted once by sulfo, and Z.sub.1 is --SO.sub.2 CH.dbd.CH.sub.2 or --SO.sub.2 CH.sub.2 CH.sub.2 Z" in which Z" is a group capable of being split by the action of an alkali;
• and
• R.sub.6 is C.sub.1 to C.sub.4 sulfoalkyl.