Monoazo dyestuffs containing diazo component substituted by disulfimide and trifluoromethyl groups

Abstract

Monoazo dyestuffs of the formula ##STR1## wherein R.sub.1 represents an aromatic radical, an aliphatic radical with 1-4 C atoms or a dialkylamino radical, in which the alkyl groups contain 1-C atoms, R.sub.2 represents hydrogen, halogen, alkyl with 1-C atoms, alkoxy with 1-4 C atoms or trifluoromethyl, R.sub.3 represents hydrogen, halogen, alkyl with 1-4 C atoms, alkoxy with 1-4 C atoms or trifluoromethyl and K represents the radical of a coupling component K-H of the formulae (II), (III) and (IV) ##STR2## wherein R.sub.4 represents alkyl with 1-4 C atoms or aryl,R.sub.5 represents hydrogen or unsubstituted alkyl with 1-4 C atoms,R.sub.6 represents hydrogen, nitrile, halogen, alkyl with 1-4 C atoms or alkoxy with 1-4 C atoms,R.sub.7 represents hydrogen, alkyl with 1-4 C atoms, aryl, a carboxylic acid ester group or a carboxylic acid amide group,R.sub.8 represents hydrogen, alkyl, cycloalkyl, aryl or the radical of a heterocyclic compound,R.sub.9 represents hydrogen, halogen, alkyl with 1-4 C atoms, alkoxy with 1-4 C atoms or acylamino,R.sub.10 represents hydrogen, halogen, alkyl with 1-4 C atoms, alkoxy with 1-4 C atoms or aryloxy,R.sub.11 represents hydrogen or alkyl,R.sub.12 represents hydrogen or alkyl and m represents 0 or 1,are suitable for the dyeing of synthetic fibre materials, especially those from polyamides. Level yellow, red and ruby shades are obtained with good dyeing yield and fastness.

Description

The invention relates to monoazo dyestuffs which in the form of the free acid correspond to the general formula ##STR3## and to their preparation and use for dyeing synthetic fibre materials, especially polyamide fibre materials.

In the general formula (I)

R.sub.1 represents an aromatic radical, an aliphatic radical with 1-4 C atoms or a dialkylamino radical, in which the alkyl groups contain 1-4 C atoms, R.sub.2 represents hydrogen, halogen, alkyl with 1-4 C atoms, alkoxy with 1-4 C atoms or trifluoromethyl, R.sub.3 represents hydrogen, halogen, alkyl with 1-4 C atoms, alkoxy with 1-4 C atoms or trifluoromethyl and K represents the radical of a coupling component K-H of the formulae (II), (III) and (IV) ##STR4## wherein R.sub.4 represents alkyl with 1-4 C atoms or aryl, R.sub.5 represents hydrogen or unsubstituted alkyl with 1-4 C atoms, R.sub.6 represents hydrogen, nitrile, halogen, alkyl with 1-4 C atoms or alkoxy with 1-4 C atoms, R.sub.7 represents hydrogen, alkyl with 1-4 C atoms, aryl, a carboxylic acid ester group or a carboxylic acid amide group, R.sub.8 represents hydrogen, alkyl, cycloalkyl, aryl or the radical of a heterocyclic compound, R.sub.9 represents hydrogen, halogen, alkyl with 1-4 C atoms, alkoxy with 1-4 C atoms or acylamino, R.sub.10 represents hydrogen, halogen, alkyl with 1-4 C atoms, alkoxy with 1-4 C atoms or aryloxy, R.sub.11 represents hydrogen or alkyl, R.sub.12 represents hydrogen or alkyl and m represents 0 or 1.

The disulphimide group of the formula (I) is in the ortho-, meta- or para-position relative to the azo bridge.

Suitable aromatic radicals R.sub.1 are, in particular, phenyl radicals. The phenyl radicals can possess further substituents, for example C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen, nitrile, nitro and the like. Phenyl and tolyl are preferred. Further suitable aromatic radicals R.sub.1 are 1- and 2-naphthyl radicals. The aliphatic radicals R.sub.1 are, in particular, alkyl radicals.

A suitable dialkylamino R.sub.1 is, for example, dimethylamino, diethylamino or dibutylamino.

Alkyl and alkoxy R.sub.2, R.sub.2, R.sub.9 and R.sub.10 can be substituted further, for example by halogen, nitrile, hydroxyl or optionally substituted phenyl, for example --CH.sub.3, --C.sub.2 H.sub.5, --C.sub.3 H.sub.7, --C.sub.4 H.sub.9, --C.sub.2 H.sub.4 CN and --CH.sub.2 --C.sub.6 H.sub.5.

A suitable alkoxy R.sub.2, R.sub.3, R.sub.6, R.sub.9 and R.sub.10 can be substituted by hydroxyl or phenyl, for example --OCH.sub.3, --OC.sub.2 H.sub.5, --OC.sub.3 H.sub.7, --OC.sub.4 H.sub.9, --OCH.sub.2 CH.sub.2 OH and --OCH.sub.2 C.sub.6 H.sub.5.

A suitable aryloxy R.sub.10 is, for example, phenoxy, which can be substituted by C.sub.1 -C.sub.4 -alkyl, especially phenoxy and tolyloxy.

A suitable alkyl R.sub.4, R.sub.6 and R.sub.7 is, in particular, unsubstituted alkyl, such as --CH.sub.3, --C.sub.2 H.sub.5, --n--C.sub.3 H.sub.7, --i--C.sub.3 H.sub.7 and --n--C.sub.4 H.sub.9.

A suitable aryl R.sub.4 is, in particular, phenyl or naphthyl which are optionally substituted further by halogen, C.sub.1 -C.sub.4 -alkyl or phenyl, for example phenyl, naphthyl, p-biphenyl, 4-chlorophenyl, 2,4-dichlorophenyl or 4-methylphenyl.

A suitable aryl R.sub.7 is preferably phenyl, which can be substituted, for example by halogen, such as fluorine, chlorine and bromine, alkyl groups or alkoxy groups each with 1-4 C atoms, especially phenyl and o--, m-- and p-tolyl.

A suitable aryl R.sub.8 is preferably phenyl, which can optionally be substituted by non-ionic substituents, such as halogen, nitrile, nitro, acylamino, C.sub.1 -C.sub.4 -alkyl, trifluoromethyl, C.sub.1 -C.sub.4 -alkoxy and amino groups which are optionally substituted by C.sub.1 -C.sub.4 -alkyl groups. A suitable acylamino is that mentioned for R.sub.9.

Suitable halogen atoms R.sub.2, R.sub.3, R.sub.6, R.sub.8, R.sub.9 and R.sub.10 are fluorine, chlorine and bromine.

A suitable alkyl R.sub.8 is in particular C.sub.1 -C.sub.4 -alkyl, for example CH.sub.3, C.sub.2 H.sub.5, n-- and iso--C.sub.3 H.sub.7 and n--, sec.- and iso-C.sub.4 H.sub.9, which can be substituted further, for example by hydroxyl, chlorine, bromine, nitrile, carbamoyl, alkoxy, especially C.sub.1 -C.sub.4 -alkoxy, alkoxycarbonyl, especially C.sub.1 -C.sub.4 -alkoxycarbonyl, or phenylalkyl, for example benzyl or 2-phenethyl.

A suitable cycloalkyl R.sub.8 has 5 to 7 C atoms and is, for example, cyclopentyl or cyclohexyl.

Suitable heterocyclic radicals R.sub.8 are, for example, the 3-sulpholanyl radical or the 2-furfuryl radical.

A suitable carbonamide R.sub.7 is, for example, that corresponding to the formula ##STR5## wherein R.sub.13 and R.sub.14 represent hydrogen or alkyl with 1-4 C atoms.

The following may be mentioned as examples: carbonamide, N-methylcarbonamide, N,N-dimethylcarbonamide, N-ethylcarbonamide, N,N-diethylcarbonamide and N-butylcarbonamide.

Suitable carboxylic acid ester groups R.sub.7 are, for example, carboxylic acid C.sub.1 -C.sub.4 -alkyl esters, such as the methyl, ethyl or butyl ester.

A suitable acylamino R.sub.9 is in particular formylamino, alkylcarbonylamino, cycloalkylcarbonylamino, alkenylcarbonylamino, phenylcarbonylamino, hetarylcarbonylamino, alkylsulphonylamino, phenylsulphonylamino and alkoxycarbonylamino, in which alkyl and phenyl can be further substituted by the substituents mentioned for R.sub.8, and alkyl, alkenyl and alkoxy preferably have 1-4 C atoms. Cycloalkyl preferably has 5-7 ring members.

A suitable acylamino R.sub.9 is, for example, formylamino, acetylamino, propionylamino, .beta.-chloropropionylamino, butyrylamino, methylsulphonylamino, phenylsulphonylamino, hydroxyacetylamino, phenoxyacetylamino, benzoylamino, p-chlorobenzoylamino, 2,5-dichlorobenzoylamino, phenacetylamino, ethoxycarbonylamino, methoxycarbonylamino and propoxycarbonylamino. Suitable hetarylcarbonyl compounds are, for example, furanoyl and thenoyl.

Alkyl R.sub.11 and R.sub.12 is in particular understood as alkyl with 1-4 C atoms, which can optionally be substituted further, for example by halogen, such as chlorine and bromine, by nitrile, hydroxyl, alkoxy with 1-4 C atoms, aryloxy, such as phenoxy or tolyloxy, or benzyloxy, by C.sub.2 -C.sub.5 -alkylcarbonyloxy, alkoxycarbonyloxy or alkoxycarbonyl, each with 1-4 C atoms in the alkoxy radical, or by aryl, for example by phenyl which is optionally substituted further.

A suitable alkyl R.sub.11 and R.sub.12 is, for example, --CH.sub.3, --C.sub.2 H.sub.5, --C.sub.3 H.sub.7, --C.sub.4 H.sub.9, --CH.sub.2 --CH.sub.2 --CN, --CH.sub.2 --CH.sub.2 --OH, --CH.sub.2 --CH.sub.2 --O--CH.sub.3, --CH.sub.2 --CH.sub.2 --O--CO--CH.sub.3, --CH.sub.2 --CH.sub.2 --O--CO--C.sub.2 H.sub.5, --CH.sub.2 --CH.sub.2 --O--CO--C.sub.3 H.sub.7, --CH.sub.2 --CH.sub.2 --O--CO--OCH.sub.3, --CH.sub.2 --CH.sub.2 --O--OC--OC.sub.2 H.sub.5, --CH.sub.2 --CH.sub.2 --O--CO--OC.sub.4 H.sub.9, --CH.sub.2 --C.sub.6 H.sub.5, --CH.sub.2 --CH.sub.2 --C.sub.6 H.sub.5, --CH.sub.2 --CH.sub.2 --Cl, --CH.sub.2 --CH.sub.2 --COO--CH.sub.3, CH.sub.2 --CH.sub.2 --COOC.sub.2 H.sub.5, ##STR6## --CH.sub.2 --CH.sub.2 --O--CO--C.sub.6 H.sub.5, --CH.sub.2 --CH.sub.2 --O--CO--CH.sub.2 --C.sub.6 H.sub.5 and --CH.sub.2 --CH.sub.2 --O--CH.sub.2 --C.sub.6 H.sub.5.

Preferred dyestuffs are those which in the form of the free acid correspond to the general formula ##STR7## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.5 have the abovementioned meaning and

R.sub.4 ' represents unsubstituted alkyl with 1-4 C atoms, or optionally substituted phenyl and R.sub.6 ' represents hydrogen, halogen or alkyl with 1-4 C atoms and the disulphimide group is in the o-, m- or p-position relative to the azo bridge, and especially those which in the form of the free acid correspond to the general formula ##STR8## wherein R.sub.1, R.sub.4 ', R.sub.5 and R.sub.6 ' have the abovementioned meaning, R.sub.2 ' represents hydrogen, chlorine, bromine, methyl, ethyl or trifluoromethyl, R.sub.3 ' represents hydrogen, chlorine, bromine, methyl, ethyl or trifluoromethyl and the disulphimide group is in the o-, m- or p-position relative to the azo bridge, in particular those which in the form of the free acid correspond to the general formula ##STR9## wherein R.sub.3 ', R.sub.4 ', R.sub.5 and R.sub.6 ' have the abovementioned meaning, R.sub.1 ' represents alkyl with 1-4 C atoms or phenyl which is optionally substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or halogen and R.sub.2 " represents chlorine, bromine, methyl, ethyl or trifluoromethyl. Particularly preferred dyestuffs are those which in the form of the free acid correspond to the general formula ##STR10## wherein R.sub.1 ', R.sub.3 ', R.sub.4 ', R.sub.5 and R.sub.6 ' have the abovementioned meaning.

Further preferred dyestuffs are those which in the form of the free acid correspond to the general formula ##STR11## wherein R.sub.1, R.sub.2 ' and R.sub.3 ' have the abovementioned meaning,

R.sub.7 ' represents methyl and R.sub.8 ' represents alkyl with 1-4 C atoms or aryl and the disulphimide group is in the o-, m- or p-position relative to the azo bridge, and especially those which in the form of the free acid correspond to the general formula ##STR12## wherein R.sub.1 ', R.sub.2 ", R.sub.3 ' and R.sub.7 ' have the abovementioned meaning and R.sub.8 " represents phenyl which is optionally substituted by halogen, C.sub.1 -C.sub.4 -alkyl or trifluoromethyl. Further preferred dyestuffs are those which in the form of the free acid correspond to the general formula ##STR13## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.9, R.sub.10 and R.sub.12 have the abovementioned meaning and R.sub.11 ' represents alkyl with 1-4 C atoms, especially those which in the form of the free acid correspond to the general formula ##STR14## wherein R.sub.1, R.sub.2 ', R.sub.3 ', R.sub.9, R.sub.11 ' and R.sub.12 have the abovementioned meaning and R.sub.10 ' represents hydrogen, chlorine, bromine, alkyl with 1-4 C atoms or alkoxy with 1-4 C atoms, especially those which in the form of the free acid correspond to the general formula ##STR15## wherein R.sub.1, R.sub.2 ", R.sub.3 ' and R.sub.11 ' have the abovementioned meaning and R.sub.9 ' represents hydrogen, chlorine, bromine, methyl, ethyl, methoxy, ethoxy or acylamino, R.sub.10 " represents hydrogen, chlorine, bromine, methyl or ethyl and R.sub.12 ' represents hydrogen or C.sub.1 -C.sub.4 -alkyl, and very particularly those which in the form of the free acid correspond to the general formula ##STR16## wherein R.sub.1 ', R.sub.2 ", R.sub.3 ', R.sub.10 ", R.sub.11 ' and R.sub.12 ' have the abovementioned meaning and R.sub.9 " represents hydrogen, methyl, ethyl, methoxy, ethoxy, C.sub.1 -C.sub.4 -alkoxycarbonylamino, C.sub.1 -C.sub.4 -alkylcarbonylamino or benzoylamino which is optionally substituted by halogen, nitro, C.sub.1 -C.sub.4 -alkyl, trifluoromethyl or C.sub.1 -C.sub.4 -alkoxy.

The new monoazo dyestuffs (I) are prepared by diazotising an amine of the formula ##STR17## wherein R.sub.1, R.sub.2 and R.sub.3 have the abovementioned meaning and coupling with a coupling component of the formula (II), (III) or (IV).

The amines of the formula XV are prepared according to known processes, for example by reaction of a sulphonamide of the formula ##STR18## with a sulphochloride of the formula R.sub.1 -SO.sub.2 -Cl in an aqueous or organic-aqueous medium. Depending on the nature of the substituents R.sub.2 and R.sub.3, it can also be necessary or desirable to react sulphonamides of the formulae ##STR19## with a sulphochloride of the formula R.sub.1 SO.sub.2 Cl and subsequently to convert the nitro group by reduction, or the acylamino group by saponification, into an amino group.

The following may be mentioned as examples of suitable amines of the formula (XV): (3-amino-4-chloro-benzenesulphonyl)-methanesulphonamide, (3-amino-4-chloro-benzenesulphonyl)-butanesulphonamide, (3-amino-4-chloro-benzenesulphonyl)-o-toluenesulphonamide, (3-amino-4-chloro-benzenesulphonyl)-benzenesulphonamide, (3-amino-6-chloro-benzenesulphonyl)-benzenesulphonamide, (3-amino-6-chloro-benzenesulphonyl)-p-toluenesulphonamide, (3-amino-6-chloro-benzenesulphonyl)-o-toluenesulphonamide, toluenesulphonamide, (2-amino-benzenesulphonyl)-benzene-sulphonamide, (2-amino-benzenesulphonyl)-p-toluenesulphonamide, (2-amino-benzenesulphonyl)-o-toluenesulphonamide, (2-amino-benzenesulphonyl)-methanesulphonamide, (2-amino-benzenesulphonyl)-butanesulphonamide, (3-amino-6-methyl-benzenesulphonyl)-benzenesulphonamide, (3-amino-6-methyl-benzenesulphonyl)-butanesulphonamide, (3-amino-6-methyl-benzenesulphonyl)-methanesulphonamide, (3-amino-6-methyl-benzenesulphonyl)-p-toluenesulphonamide, (3-amino-6-methyl-benzenesulphonyl)-o-toluenesulphonamide, (3-amino-4-methyl-benzenesulphonyl)-benzenesulphonamide, (3-amino-4-methyl-benzenesulphonyl)-p-toluenesulphonamide, (3-amino-4-methyl-benzenesulphonyl)-o-toluenesulphonamide, (3-amino-4-methyl-benzenesulphonyl)-methanesulphonamide, (3-amino-4-methoxy-benzenesulphonyl)-benzenesulphonamide, (3-amino-4-methoxy-benzenesulphonyl)-p-toluenesulphonamide, (3-amino-4-methoxy-benzenesulphonyl)-methanesulphonamide, (3-amino-4-methoxy-benzenesulphonyl)-butanesulphonamide, (3-amino-6-methoxy-benzenesulphonyl)-benzenesulphonamide, (3-amino-6-methoxy-benzenesulphonyl)-p-toluenesulphonamide, (3-amino-6-methoxy-benzenesulphonyl)-methanesulphonamide, (3-amino-6-methoxy-benzenesulphonyl)-butanesulphonamide, (3-amino-6-ethyl-benzenesulphonyl)-benzenesulphonamide, (3-amino-6-ethyl-benzenesulphonyl)-p-toluenesulphonamide, (3-amino-6-ethyl-benzenesulphonyl)-methanesulphonamide, (3-amino-4-ethyl-benzenesulphonyl)-benzenesulphonamide, (3-amino-6-ethoxy-benzenesulphonyl)-benzenesulphonamide, (3-amino-6-ethoxy-benzenesulphonyl)-p-toluenesulphonamide, (4-amino-benzenesulphonyl)-p-toluenesulphonamide, (4-amino-benzenesulphonyl)-o-toluenesulphonamide, (4-amino-benzenesulphonyl)-methanesulphonamide, (4-amino-benzenesulphonyl)-butanesulphonamide, (3-amino-4-bromo-benzenesulphonyl)-benzenesulphonamide, (3-amino-4-bromobenzenesulphonyl)-p-toluenesulphonamide, (3-amino-4-bromobenzenesulphonyl)-o-toluenesulphonamide, (3-amino-4-bromobenzenesulphonyl)-methanesulphonamide, (3-amino-4-bromobenzenesulphonyl)-butanesulphonamide, (2-amino-3-chloro-4-methyl-benzenesulphonyl)-benzenesulphonamide, (2-amino-3-chloro-4-methoxy-benzenesulphonyl)-benzenesulphonamide, (3-amino-4-chloro-5-methyl-benzenesulphonyl)-benzenesulphonamide, (3-amino-5-chloro-6-methyl-benzenesulphonyl)-benzenesulphonamide, (3-amino-5-chloro-6-methyl-benzenesulphonyl)-methanesulphonamide, (3-amino-benzenesulphonyl)-1-naphthylsulphonamide, (4-amino-benzenesulphonyl)-2-naphthylsulphonamide, (3-amino-benzenesulphonyl)-N,N-dimethylaminosulphonamide, (4-amino-benzenesulphonyl)-N,N-diethylaminosulphonamide, (3-amino-benzenesulphonyl)-N,N-dibutylaminosulphonamide, (3-amino-4-trifluoromethyl-benzenesulphonyl)-methanesulphonamide, (3-amino-4-trifluoromethyl-benzenesulphonyl)-p-toluenesulphonamide, (3-amino-4-trifluoromethyl-benzenesulphonyl)benzenesulphonamide, (3-amino-benzenesulphonyl)-o-toluenesulphonamide, (3-amino-4-chloro-benzenesulphonyl)-p-toluenesulphonamide, (3-amino-benzenesulphonyl)-benzenesulphonamide, (3-amino-chloro-benzenesulphonyl)-benzenesulphonamide, (3-amino-benzenesulphonyl)-methanesulphonamide, (3-amino-benzenesulphonyl)-propanesulphonamide, (3-amino-benzenesulphonyl)butanesulphonamide, (3-amino-benzenesulphonyl)-p-toluenesulphonamide, (4-amino-3-trifluoromethyl-benzenesulphonyl)benzenesulphonamide, (4-amino-3-trifluoromethyl-benzenesulphonyl)-methanesulphonamide, (4-amino-3-trifluoromethylbenzenesulphonyl)-butanesulphonamide, (4-amino-3-trifluoromethyl-benzenesulphonyl)-p-toluenesulphonamide, (4-amino-3-trifluoromethyl-benzenesulphonyl)-o-toluenesulphonamide, (4-amino-3-trifluoromethyl-benzenesulphonyl)-2-naphthylsulphonamide, (4-amino-3-chloro-benzenesulphonyl)-benzenesulphonamide, (4-amino-3-chloro-benzenesulphonyl)-p-toluenesulphonamide, (4-amino-3-chloro-benzenesulphonyl)-methanesulphonamide, (4-amino-3-chloro-benzenesulphonyl)-dimethylaminosulphonamide, (4-amino-3-bromo-benzenesulphonyl)-benzenesulphonamide, (4-amino-3-bromo-benzenesulphonyl)-methanesulphonamide, (4-amino-3-bromo-benzenesulphonyl)-p-toluenesulphonamide, (4-amino-3-methyl-benzenesulphonyl)-benzenesulphonamide, (4-amino-3-methyl-benzenesulphonyl)-methanesulphonamide, (4-amino-3-methyl-benzenesulphonyl)-o-toluenesulphonamide, (4-amino-3-methyl-benzenesulphonyl)-p-toluenesulphonamide, (4-amino-2,5-dichloro-benzenesulphonyl)-benzenesulphonamide, (4-amino-2,5-dichloro-benzenesulphonyl)-methanesulphonamide, (4-amino-2,5-dichloro-benzenesulphonyl)-propanesulphonamide, (4-amino-2,5-dichloro-benzenesulphonyl)-p-toluenesulphonamide, (4-amino-2,5-dichloro-benzenesulphonyl)o-toluenesulphonamide, (4-amino-2,5-dichloro-benzenesulphonyl)-butanesulphonamide, (4-amino-2,5-dichloro-benzenesulphonyl)dimethylaminosulphonamide, (4-amino-3,5-dichloro-benzenesulphonyl)-benzenesulphonamide, (4-amino-3,5-dichloro-benzenesulphonyl)-p-toluenesulphonamide, (4-amino-3,5-dichlorobenzenesulphonyl)-methanesulphonamide, (4-amino-2-chloro-5-trifluoromethyl-benzenesulphonyl)-benzenesulphonamide, (4-amino-2-chloro-5-trifluoromethyl-benzenesulphonyl)-methanesulphonamide, (4-amino-2-chloro-5-trifluoromethyl-benzenesulphonyl)-butanesulphonamide, (4-amino-2-chloro-5-trifluoromethyl-benzenesulphonyl)-p-toluenesulphonamide, ( 4-amino-2-chloro-5-trifluoromethyl-benzenesulphonyl)-o-toluenesulphonamide, (4-amino-2-chloro-5-trifluoromethyl-benzenesulphonyl)-2-naphthylsulphonamide, (4-amino-3-methyl-benzenesulphonyl)methanesulphonamide, (4-amino-3-methyl-benzenesulphonyl)ethanesulphonamide, (4-amino-3-methyl-benzenesulphonyl)butanesulphonamide, (4-amino-3-methyl-benzenesulphonyl)benzenesulphonamide, (4-amino-3-methyl-benzenesulphonyl)-p-toluenesulphonamide, (4-amino-3-methyl-benzenesulphonyl)-o-toluenesulphonamide, (4-amino-2-trifluoromethyl-5-chlorobenzenesulphonyl)-benzenesulphonamide, (4-amino-2-trifluoromethyl-5-chloro-benzenesulphonyl)-p-toluenesulphonamide, (4-amino-2-trifluoromethyl-5-chloro-benzenesulphonyl)-o-toluenesulphonamide, (4-amino-2-trifluoromethyl-5-chloro-benzenesulphonyl)-2-naphthylsulphonamide, (4-amino-2-trifluoromethyl-5-bromo-benzenesulphonyl)-benzenesulphonamide, (4-amino-2-trifluoromethyl-5-bromo-benzenesulphonyl)-methanesulphonamide, (4-amino-2-trifluoromethyl-5-bromo-benzenesulphonyl)-butanesulphonamide, (4-amino-2-trifluoromethyl-5-bromo-benzenesulphonyl)-o-toluenesulphonamide, (4-amino-2-trifluoromethylbenzenesulphonyl)-methanesulphonamide, (4-amino-2-trifluoromethyl-benzenesulphonyl)-butanesulphonamide, (4-amino-2-trifluoromethyl-benzenesulphonyl)-benzenesulphonamide, (4-amino-2-trifluoromethyl-benzenesulphonyl)-p-toluenesulphonamide (4-amino-2-methyl-5-chloro-benzenesulphonyl)-benzenesulphonamide, (4-amino-2-methyl-5-chloro-benzenesulphonyl9-p-toluenesulphonamide, (4-amino-2-methyl-5-chloro-benzenesulphonyl)-o-toluenesulphonamide, (4-amino-2-methyl-5-trifluoromethylbenzenesulphonyl)-methanesulphonamide, (4-amino-2-methyl-5-trifluoromethyl-benzenesulphonyl)-benzenesulphonamide, (4-amino-2,5-dibromo-benzenesulphonyl)-benzenesulphonamide, (4-amino-2,5-dibromo-benzenesulphonyl)-p-toluenesulphonamide, (4-amino-2,5-dibromo-benzenesulphonyl)-o-toluenesulphonamide, (4-amino-2,5-dibromo-benzenesulphonyl)-2-naphthylsulphonamide, (4-amino-2,5-dibromo-benzenesulphonyl)-dimethylaminosulphonamide, (4-amino-2,5-dimethyl-benzenesulphonyl)-benzenesulphonamide, (4-amino-2,5-dimethyl-benzenesulphonyl)-methanesulphonamide, (4-amino-2,5-dimethyl-benzenesulphonyl)-butanesulphonamide, (4-amino-2,5-dimethyl-benzenesulphonyl)-p-toluenesulphonamide and (4-amino-2,5-dimethyl-benzenesulphonyl)-o-toluenesulphonamide.

Examples of suitable coupling components of the formula (II) are: 2-methyl-indole, 2-phenyl-indole, 1-methyl-2-phenyl-indole, 1,2-dimethyl-indole, 2-.beta.-naphthyl-indole, 2,5-dimethyl-indole, 2,4-dimethyl-7-methoxy-indole, 2-phenyl-5-ethoxy-indole, 2-methyl-5-ethoxyindole, 2-methyl-5-chloro-indole, 2-methyl-6-chloro-indole, 2-methyl-5-nitro-indole, 2-methyl-5-cyano-indole, 2-methyl-7-chloro-indole, 2-methyl-5-fluoro-indole, 2-methyl-5-bromoindole and 2-methyl-5,7-dichloro-indole, and also the indolesulphonic acid described in German Patent Specification No. 137,117 and other indole-sulphonic acids prepared, analogously to the process described in German Patent Specification 137,117, from 2-alkyl- or 2-aryl-indoles, for example 2-methylindole-sulphonic acid, 1,2-dimethyl-indole-sulphonic acid, 2,5-dimethyl-indole-sulphonic acid, 1-ethyl-2-methyl-indolesulphonic acid, 1,2,5-trimethyl-indole-sulphonic acid, 1-ethyl-2,5-dimethyl-indole-sulphonic acid, 2-phenyl-indolesulphonic acid and 1-methyl-2-phenyl-indole-sulphonic acid. It is probable that at least in the case of the indoles which are unsubstituted in the carbocyclic part, the sulpho group enters the 5-position in the sulphonation by the process described in German Patent Specification No. 137,117.

Examples of suitable coupling components of the formula (III) are: 1-isopropyl-3-methyl-5-aminopyrazole, 1-(.beta.-hydroxyethyl)-3-methyl-5-aminopyrazole, 1,3-dimethyl-5-aminopyrazole, 1-methyl-3-phenyl-5-aminopyrazole, 1-ethyl-3-methyl-5-aminopyrazole, 1-(2-furfuryl)-3-methyl-5-aminopyrazole, 1-(.beta.-cyanoethyl)-3-methyl-5-aminopyrazole, 1-(.beta.-phenylethyl)-3-methyl-5-aminopyrazole, 1-isobutyl-3-methyl-5-aminopyrazole, 1-(1,2-dimethyl-n-propyl)-3-methyl-5-aminopyrazole, 1-benzyl-3-methyl-5-aminopyrazole, 1-phenyl-3-ethyl-5-aminopyrazole, 1-(3-methoxyphenyl)-3-methyl-5-aminopyrazole, 1-(2-methylphenyl)-3-methyl-5-aminopyrazole, 1-(4-aminophenyl)-3-methyl-5-aminopyrazole, 1-(2-phenyl-propyl)-5-aminopyrazole, 1-(3-methylphenyl)-3-methyl-5-aminopyrazole, 1-(4-ethoxyphenyl)-3-methyl-5-aminopyrazole, 1-(2-methoxy-5-methylphenyl)-3-methyl-5-aminopyrazole, 1-cyclohexyl-3-methyl-5-aminopyrazole, 1-(4-methylphenyl)-3-methyl-5-aminopyrazole, 1-(4-methoxyphenyl)-3-methyl-5-aminopyrazole, 1-(2,6-dimethylphenyl)-3-methyl-5-aminopyrazole, 1-(2-chlorophenyl)-3-methyl-5-aminopyrazole, 1-(3-chlorophenyl)-3-methyl-5-aminopyrazole, 1-(4-chlorophenyl)-3-methyl-5-aminopyrazole, 1-(3-nitrophenyl)-3 -methyl-5-aminopyrazole, 1-(4-nitrophenyl)-3-methyl-5-aminopyrazole, 1-(2-trifluoromethyl-phenyl)-3-methyl-5-aminopyrazole and 1-(2,5-dichlorophenyl)-3-methyl-5-aminopyrazole.

Examples of suitable coupling components of the formula (IV) are: N,N-dimethylaniline, N,N-diethylaniline, N-methyl-N-n-butylaniline, N,N-diethyl-m-toluidine, N,N-diethylamino-3-chlorobenzene, N,N-diethyl-N'-formyl-m-phenylenediamine, N,N-diethyl-N'-acetyl-m-phenylenediamine, N,N-diethyl-N'-propionyl-m-phenylenediamine, N,N-diethylamino-3-methoxybenzene, 1-N,N-diethylamino-2,5-dimethoxybenzene, 1-N,N-diethylamino-2,5-diethoxybenzene, 1-N,N-diethylamino-2-methoxy-3-acetylaminobenzene, N-ethyl-N-.beta.-chloroethylaniline, N,N-bis-(.beta.-chloroethyl)-aniline, N-(.beta.-chloroethyl)-N-butyl-aniline, N-(.beta.-chloroethyl)-N-ethyl-m-toluidine, N,N-bis-(.beta.-chloroethyl)-m-toluidine, N-methyl-N-.beta.-hydroxyethylaniline, N-ethyl-N-.beta.-hydroxyethyl-aniline, N,N-bis-(.beta.-hydroxyethyl)-aniline, N-butyl-N-(.beta.-hydroxyethyl)-aniline, N,N-bis-(.beta.,.gamma.-dihydroxypropyl)-aniline, N-ethyl-N-benzyl-aniline, N-ethyl-N-benzyl-m-toluidine, N-ethyl-N-.beta.-hydroxyethyl-m-toluidine, N,N-bis-(.beta.-hydroxyethyl)-m-toluidine, 1-(N-ethyl-N-.beta.-hydroxyethyl)-amino-2-methoxy-5-methylbenzene, N-ethyl-N-.beta.-hydroxyethyl-N'-acetyl-m-phenylenediamine, N,N-bis-(.beta.-hydroxyethyl)-N'-acetyl-m-phenylenediamine, 1-N,N-bis-(.beta.-hydroxyethyl)-amino-2-methoxy-5-acetylaminobenzene, 1-N,N-bis-(.beta.-hydroxyethyl)-amino-2-ethoxy-5-acetylaminobenzene, 1-N,N-bis-(.beta.-hydroxyethyl)-amino-2-methoxy-5-propionylaminobenzene, N-ethyl-N-.beta.-acetoxyethylaniline, N,N-bis-(.beta.-acetoxy-ethyl)-aniline, N-butyl-N-.beta.-acetoxyethyl-aniline, N-ethyl-N-.beta.-acetoxyethyl-m-toluidine, N,N-bis-(.beta.-acetoxyethyl)-m-toluidine, 1-N-ethyl-N-.beta.-acetoxyethylamino-2-methoxy-5-methylbenzene, N-ethyl-N-.beta.-acetoxyethyl-N'-acetyl-m-phenylenediamine, N,N-bis-(.beta.-acetoxyethyl)-N'-acetyl-m-phenylenediamine, 1-N,N-bis-(.beta.-acetoxyethyl)-amino-2-methoxy-5-acetylamino-benzene, 1-N,N-bis-(.beta.-acetoxyethyl)-amino-2-ethoxy-5-acetylamino-benzene, 1-N,N-(.beta.-acetoxyethyl)-amino-2-methoxy-5-propionylaminobenzene, N,N-bis-(.beta.-ethoxycarbonyloxyethyl)-aniline, N,N-bis-(.beta.-methoxycarbonyloxyethyl)-aniline, N,N-bis-(.beta.-ethoxycarbonyloxyethyl)-m-toluidine, N,N-bis-(.beta.-methoxycarbonyloxyethyl)-m-toluidine, N,N-bis-(.beta.-ethoxycarbonyloxyethyl)-N'-acetyl-m-phenylenediamine, N,N-bis-(.beta.-methoxycarbonyloxyethyl)-N'-acetyl-m-phenylenediamine, 1-N,N-bis-(.beta.-ethoxycarbonyloxyethyl)-amino-2-methoxy-5-acetylaminobenzene, 1-N,N-bis-(.beta.-methoxycarbonyloxyethyl)-amino-2-methoxy-5-acetylaminobenzene, 1-N,N-bis-(.beta.-ethoxycarbonyloxyethyl9-amino-2-ethoxy-5-acetyl-aminobenzene, 1-N,N-bis-(.beta.-methoxycarbonyloxyethyl)-amino-2-ethoxy-5-acetylaminobenzene, N,N-bis-(.beta.-carbomethoxy-ethyl)-N'-acetyl-m-phenylenediamine, N-methyl-N-.beta.-cyanoethyl-aniline, N,N-bis-(.beta.-cyanoethyl)-aniline, N-ethyl-N-.beta.-cyanoethyl-m-toluidine, N-ethyl-N-.beta.-cyanoethyl-N'-acetylamino-m-phenylenediamine, N-.beta.-hydroxyethyl-N-.beta.-cyanoethylaniline, N-.beta.-acetoxy-ethyl-N-.beta.-cyanoethyl-m-toluidine, N-.beta.-methoxycarbonyloxyethyl-N-.beta.-cyanoethyl-N'-acetyl-m-phenylenediamine, N,N-bis-(.beta.-cyanoethyl)-N'-benzoyl-m-phenylenediamine, N-.beta.-hydroxyethyl-N-.beta.-cyanoethyl-N'-phenacetyl-m-phenylenediamine, N,N-diethyl-N'-phenoxyacetyl-m-phenylenediamine, N-ethyl-N-.beta.-cyanoethyl-N'-phenoxyacetyl-m-phenylenediamine, N,N-bis-(.beta.-cyanoethyl)-N'-p-chlorobenzoyl-m-phenylenediamine, N-ethyl-N-.beta.-phenylethylaniline, N-ethyl-N-.beta.-phenylethyl-m-toluidine, N-butyl-N-.beta.-phenylethyl-aniline, N-butyl-N-.beta.-phenylethyl-m-toluidine, N-.beta.-cyanoethyl-N-.beta.-phenylethyl-aniline, N-.beta.-cyanoethyl-N-.beta.-phenylethyl-m-toluidine, N-ethyl-N-.beta.-methoxyethyl-aniline, N-ethyl-N-.beta.-methoxyethyl-m-toluidine, 1-N,N-diethylamino-2-methoxy-5-methanesulphonylamino-benzene, 1-N,N-bis-(.beta.-hydroxyethyl)-amino-2-ethoxy-5-benzenesulphonylamino-benzene, 1-(N-ethyl-N-.beta.-cyanoethyl)-amino-2-methoxy-5-formylamino-benzene, 1-(N-methyl-N-ethyl)-amino-2-ethoxy-5-benzenesulphonylaminobenzene, 1-N,N-dipropylamino-2-methoxy-5-ethanesulphonylaminobenzene, N,N-diethylamino-N'-acryloyl-m-phenylenediamine, 1-N,N-diethylamino-2-methoxy-5-methacryloylamino-benzene, 1-(N-.beta.-acetoxyethyl-N-ethyl)-amino-2-ethoxy-5-(2'-thenoylamino)benzene, 1-(N-ethyl-N-.beta.-cyanoethyl)-amino-2-methoxy-5-cyclohexylcarbonylamino-benzene, N,N-diethylamino-N'-ethoxycarbonyl-m-phenylenediamine, 1-(N-.beta.-acetoxyethyl-N-ethyl)-amino-2-methoxy-5-methoxycarbonylamino-benzene, 1-(N-.beta.-cyanoethyl-N-ethyl)-amino-2-ethoxy-5-propoxycarbonylamino-benzene and 1-(N-.beta.-hydroxyethyl-N-ethyl)-amino-2-methoxy-5-ethoxycarbonylamino-benzene.

The dyestuffs according to the invention are suitable for dyeing natural and synthetic fibre materials, for example of wool, silk and polyamide, and especially for dyeing polyamide fibres in level yellow, red and ruby shades of good dyeing yield and good level of fastness.

By polyamide fibres there are in particular understood those of synthetic polyamides such as .epsilon.-polycaprolactam or condensation products of adipic acid and hexamethylenediamine. The dyestuffs can be employed either in the form of the free acids (--SO.sub.2 --NH--SO.sub.2 --) or in the form of their salts, especially of the alkali metal salts, especially of the sodium salts or of the ammonium salts, but also in the form of the lithium salts.

The diazotisation of the amines of the formula (XV) is carried out according to known methods, preferably in aqueous mineral acid solution, using sodium nitrite. The coupling of the diazonium compounds of the amines of the formula (XV) with the coupling components of the formulae (II), (III) and (IV) can be carried out according to known processes, for example in a neutral to strongly acid pH range, but preferably in a weakly acid pH range, in an aqueous or organic-aqueous medium.

The more sparingly soluble dyestuffs (I) can be rendered readily water-soluble by mixing them with salts of strong bases and weak acids, for example trisodium phosphate, disodium hydrogen phosphate, sodium tetraborate, sodium metaphosphate, sodium metasilicate or sodium carbonate.

The new dyestuffs of the formula (I) can be isolated in the form of the free acid or as alkali metal salts or ammonium salts. Examples of suitable alkali metal salts, in which the hydrogen atom of the --SO.sub.2 --NH--SO.sub.2 -- group is thus replaced by an alkali metal cation, are the sodium, potassium or lithium salts.

EXAMPLE 1

38 g of (4-amino-3-trifluoromethyl-benzenesulphonyl)benzenesulphonamide are dissolved in 800 ml of water by means of a little sodium hydroxide solution, at pH 9 and 70.degree. C.; 7.0 g of sodium nitrite are added. This solution is added, over the course of 30 minutes, to 30 ml of (37% strength) hydrochloric acid at 0.degree.-5.degree. C. and the mixture is stirred for 30 minutes at 0.degree.-5.degree. C. A solution of 18.7 g of N-ethyl-N-.beta.-cyanoethyl-m-toluidine in 100 ml of 10% strength hydrochloric acid is added to the colourless suspension of the diazonium compound and the coupling which takes place immediately is completed by addition of sodium acetate. After salting out, the dyestuff of the formula ##STR20## is filtered off and dried. The dyestuff dyes polyamide, from a weakly acid or neutral bath, in yellowish-tinged orange shades of a good level of fastness.

Dyeing example

0.1 g of the dyestuff of Example 1 is dissolved in 100 ml of hot water, 5 ml of 10% strength ammonium acetate solution are added and the mixtutre is diluted to a volume of 500 ml with water. 10 g of polyamide fibres are introduced into the dyebath, the latter is brought to the boil over the course of 20 minutes, 4 ml of 10% strength acetic acid are added and the bath is kept at the boil for one hour. The fibres are then rinsed, and dried at 70.degree.-80.degree. C.

EXAMPLE 2

If the procedure in Example 1 is followed, using 13.1 g of 2-methyl-indole, dissolved in 150 ml of glacial acetic acid, for the coupling reaction in place of diethyl-m-toluidine, a dyestuff is obtained which in the form of the free acid corresponds to the formula ##STR21## and dyes synthetic polyamides in yellow shades of excellent fastness properties.

EXAMPLE 3

If the procedure in Example 1 is followed, using 19.3 g of 2-phenyl-indole, dissolved in 150 ml of glacial acetic acid, for the coupling reaction in place of diethyl-m-toluidine, a dyestuff is obtained which in the form of the free acid corresponds to the formula ##STR22## and dyes synthetic polyamides in reddish-tinged yellow shades of excellent fastness properties.

EXAMPLE 4

The procedure in Example 1 is followed, but 17.3 g of 1-phenyl-3-methyl-5-aminopyrazole hydrochloride in 150 ml of water are used for the coupling reaction instead of diethyl-m-toluidine, and the mixture is buffered to pH 4-5 with sodium acetate. After completion of the coupling reaction, the dyestuff, which in the form of the free acid corresponds to the formula ##STR23## is filtered off and dried. It dyes polyamide fibres and polyamide fabrics, from a weakly acid or neutral bath, in greenish-tinged yellow shades of a good level of fastness.

If the procedure described in Examples 1 to 4 is followed and the diazo components employed are the compounds listed in column I, and the coupling components employed are the compounds listed in column II of the table which follows, valuable water-soluble dyestuffs are again obtained, which dye polyamide from a weakly acid or neutral bath. Aniline derivatives used as coupling components here give orange, red and ruby shades, indole derivatives give yellow shades and derivatives of 5-aminopyrazole give greenish-tinged yellow shades.

__________________________________________________________________________Example I II__________________________________________________________________________5 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- N,N-dimethyl-aniline benzenesulphonamide6 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- N,N-di-n-propylaniline benzenesulphonamide7 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- N-ethyl-N-.beta.-cyanoethylaniline benzenesulphonamide8 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- N,N-diethylaniline benzenesulphonamide9 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- N-ethyl-N-benzylaniline benzenesulphonamide10 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- N-ethyl-N-.beta.-phenylethyl-3-methylaniline benzenesulphonamide11 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- N-.beta.-methoxyethyl-N-ethyl-3-methylaniline 2 benzenesulphonamide12 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- N-ethyl-N-.beta.-phenylethylaniline benzenesulphonamide13 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- N,N-diethyl-3-acetylaminoaniline benzensulphonamide14 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- N-ethyl-N-benzyl-3-methylaniline benzenesulphonamide15 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- N-ethyl-N-.beta.-hydroxyethylaniline benzenesulphonamide16 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- N-ethyl-N.beta.-hydroxyethyl-3-methylaniline benzenesulphonamide17 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- N-ethyl-N-.beta.methoxyethylaniline benzenesulphonamide18 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- N,N-di-n-butylaniline benzenesulphonamide19 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- 1-methyl-2-phenyl-indole benzenesulphonamide20 (4-Amino-3-trifluoromethyl-benzenesulphonyl) 1,2-dimethyl-indole benzenesulphonamide21 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- 2-.beta.-naphthylindole benzenesulphonamide22 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- 2-p-diphenylyl-indole benzenesulphonamide23 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- 1,2,5-trimethyl-indole benzenesulphonamide24 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- 1-ethyl-2-methyl-indole benzenesulphonamide25 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- 2-methyl-6-chloro-indole benzenesulphonamide26 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- 2-methyl-7-chloro-indole benzenesulphonamide27 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- 2-methyl-5,7-dichloro-indole benzenesulphonamide28 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- 2-methyl-5-methoxy-indole29 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- 2-methyl-5-bromo-indole benzenesulphonamide30 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- 2-methyl-5-fluoro-indole benzenesulphonamide31 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- 2-methyl-indol-sulphonic acid benzenesulphonamide32 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- 2-phenyl-indole-sulphonic acid benzenesulphonamide33 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- 1-methyl-2-phenyl-indole-sulphonic acid benzenesulphonamide34 (4-amino-4-trifluoromethyl-benzenesulphonyl)- N,N-diethyl-3-chloroaniline p-toluenesulphonamide35 (4-amino-3-trifluoromethyl-benzenesulphonyl)- N,N-di-n-butylaniline p-toluenesulphonamide36 (4-amino-3-trifluoromethyl-benzenesulphonyl)- N-.beta.-cyanoethyl-3-chloroaniline p-toluenesulphonamide37 (4-amino-3-trifluoromethyl-benzenesulphonyl)- N-.beta.cyanoethyl-2-methoxy-5-methylaniline p-toluenesulphonamide38 (4-amino-3-trifluoromethyl-benzenesulphonyl)- N,N-diethyl-3-acetylaminoaniline p-toluenesulphonamide39 (4-amino-3-trifluoromethyl-benzenesulphonyl)- N-ethyl-N-.beta.cyanoethyl-3-methylaniline p-toluenesulphonamide40 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- N-ethyl-N-.beta.-cyanoethylaniline p-toluenesulphonamide41 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- N,N-diethylaniline p-toluenesulphonamide42 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- N-ethyl-N-.beta.-phenylethylaniline p-toluenesulphonamide43 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- N-ethyl-N-.beta.-phenylethyl-3-methylaniline p-toluenesulphonamide44 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- 2-methyl-indole p-toluenesulphonamide45 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- 2-phenyl-indole p-toluenesulphonamide46 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- 1-methyl-2-phenyl-indole p-toluenesulphonamide47 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- 2-methyl-indole-sulphonic acid p-toluenesulphonamide48 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- 2-phenyl-indole-sulphonic acid p-toluenesulphonamide49 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- 1-methyl-2-phenyl-indole-sulphonic acid p-toluenesulphonamide50 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- 1-ethyl-2-methyl-indole p-toluenesulphonamide51 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- N-.beta.-cyanoethyl-3-acetylaminoaniline o-toluenesulphonamide52 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- N-butyl-N-.beta.-phenylethylaniline o-toluenesulphonamide53 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- N-butyl-N-.beta.-phenylethyl-3-methylaniline o-toluenesulphonamide54 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- N-.beta.-cyanoethyl-N-.beta.-phenylethylanilin e o-toluenesulphonamide55 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- N,N-di-.beta.-acetoxyethyl-3-methylaniline o-toluenesulphonamide56 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- N,N-diethyl-3-chloroaniline o-toluenesulphonamide57 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- N,N-di-.beta.-methoxyethylaniline o-toluenesulphonamide58 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- N-ethyl-N-.beta.-propionoxyethylaniline o-toluenesulphonamide59 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- N-ethyl-N-.beta.-methoxycarbonyloxyethylanilin e o-toluenesulphonamide60 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- N-ethyl-N-.beta.-methoxycarbonylethylaniline o-toluenesulphonamide61 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- N-ethyl-N-.beta.-ethoxycarbonylethylaniline o-toluenesulphonamide62 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- N-ethyl-N-.beta.-chloroethylaniline o-toluenesulphonamide63 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- 2-methyl-indole o-toluenesulphonamide64 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- 2-phenyl-indole o-toluenesulphonamide65 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- N-ethyl-N-.beta.-hydroxyethylaniline methanesulphonamide66 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- N-ethyl-N-.beta.-hydroxyethyl-3-methylaniline . methanesulphonamide67 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- N,N-di-n-propyl-3-methylaniline methanesulphonamide68 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- N-ethyl-N-benzyl-3-methylaniline methanesulphonamide69 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- N-.beta.-cyanoethyl-N-.beta.-acetoxyethyl-3-me thyl- methanesulphonamide aniline70 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- N,N-diethyl-3-benzoylaminoaniline methanesulphonamide71 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- N,N-diethyl-3-methylaniline methanesulphonamide72 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- 2-methyl-indole-sulphonic acid methanesulphonamide73 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- 2-phenyl-indole-sulphonic acid methanesulphonamide74 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- 1-methyl-2-phenyl-indole-sulphonic acid methanesulphonamide75 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- 2-methyl-indole methanesulphonamide76 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- 2-phenyl-indole methanesulphonamide77 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- 1-methyl-2-phenyl-indole methanesulphonamide78 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- 1,2-dimethyl-indole methanesulphonamide79 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- 2-methyl-5-methoxy-indole methanesulphonamide80 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- 2-methyl-5-bromo-indole methanesulphonamide81 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- 2-methyl-5-fluoro-indole methanesulphonamide82 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- 1-phenyl-3-methyl-5-aminopyrazole methanesulphonamide83 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- 1-(2-chlorophenyl)-3-methyl-5-aminopyrazole methanesulphonamide84 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- 1-(4-tolyl)-3-methyl-5-aminopyrazole methanesulphonamide85 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- 1-(3-chlorophenyl)-3-methyl-5-aminopyrazole methanesulphonamide86 (4-Amino-3-trifluoromethyl-benzenesulphonyl)- 1-(4-chlorophenyl)-3-methyl-5-aminopyrazole methanesulphonamide87 (4-Amino-2-chloro-5-trifluoromethyl- N,N-diethylaniline benzenesulphonyl)-benzenesulphonamide88 (4-Amino-2-chloro-5-trifluoromethyl- N,N-diethyl-3-methylaniline benzenesulphonyl)-benzenesulphonamide89 (4-Amino-2-chloro-5-trifluoromethyl- N-ethyl-N-.beta.-cyanoethylaniline benzenesulphonyl)-benzenesulphonamide90 (4-Amino-2-chloro-5-trifluoromethyl- N,N-di-.beta.-cyanoethyl-3-methylaniline benzenesulphonyl)-benzenesulphonamide91 (4-Amino-2-chloro-5-trifluoromethyl- N-ethyl-N-.beta.-phenylethyl-3-methylaniline benzenesulphonyl)-benzenesulphonamide92 (4-Amino-2-chloro-5-trifluoromethyl- N,N-dipropyl-3-methylaniline benzenesulphonyl)-benzenesulphonamide93 (4-Amino-2-chloro-5-trifluoromethyl- N-.beta.-cyanoethyl-2-methoxy-5-methylaniline benzenesulphonyl)-benzenesulphonamide94 (4-Amino-2-chloro-5-trifluoromethyl- N,N-diethyl-2-ethoxy-5-acetylaminoaniline benzenesulphonyl)-benzenesulphonamide95 (4-Amino-2-chloro-5-trifluoromethyl- N,N-diethyl-3-benzoylaminoaniline benzenesulphonyl)-benzenesulphonamide96 (4-Amino-2-chloro-5-trfluoromethyl- N-ethyl-2-chloro-aniline benzenesulphonyl)-benzenesulphonamide97 (4-Amino-2-chloro-5-trifluoromethyl- 2-methyl-indole benzenesulphonyl)-benzenesulphonamide98 (4-Amino-2-chloro-5-trifluoromethyl- benzenesulphonyl)-benzenesulphonamide99 (4-Amino-2-chloro-5-trifluoromethyl- 2-phenyl-indole benzenesulphonyl)-benzenesulphonamide100 (4-Amino-2-chloro-5-trifluoromethyl- 1-methyl-2-phenyl-indole benzenesulphonyl)-benzenesulphonamide101 (4-Amino-2-chloro-5-trifluoromethyl- 2-methyl-5-methoxy-indole benzenesulphonyl)-benzenesulphonamide102 (4-Amino-2-chloro-5-trifluoromethyl- 2-methyl-6-chloro-indole benzenesulphonyl)-benzenesulphonamide103 (4-Amino-2-chloro-5-trifluoromethyl- 1-(2-trifluoromethylphenyl)-3-methyl-5- benzenesulphonyl)-benzenesulphonamide aminopyrazole104 (4-Amino-2-chloro-5-trifluoromethyl- 1-phenyl-3-methyl-5-ainopyrazole benzenesulphonyl)-benzenesulphonamide105 (4-Amino-2-chloro-5-trifluoromethyl- 1-(3-chlorophenyl)-3-methyl-5-aminopyrazole benzenesulphonyl)-benzenesulphonamide106 (4-Amino-2-chloro-5-trifluoromethyl- N,N-dimethyl-3-benzoylaminoaniline benzenesulphonyl)-butanesulphonamide107 (4-Amino-2-chloro-5-trifluoromethyl- N,N-diethyl-3-methoxyaniline benzenesulphonyl)-butanesulphonamide108 (4-Amino-2-chloro-5-trifluoromethyl- N-.beta.-cyanoethyl-3-acetylaminoaniline benzenesulphonyl)-butanesulphonamide109 (4-Amino-2-chloro-5-trifluoromethyl- N-ethyl-N-.beta.-hydroxyethyl-3-methylaniline benzenesulphonyl)-butanesulphonamide110 (4-Amino-2-chloro-5-trifluoromethyl- N,N-di-.beta.-methoxyethylaniline benzenesulphonyl)-butanesulphonamide111 (4-Amino-2-chloro-5-trifluoromethyl- N-.beta.-cyanoethyl-N-benzyl-3-methylaniline benzenesulphonyl)-butanesulphonamide112 (4-Amino-2-chloro-5-trifluoromethyl- N-ethyl-N-.beta.-hydroxyethyl-3-benzenesulphon yl- benzenesulphonyl)-butanesulphonamide amino-aniline113 (4-Amino-2-chloro-5-trifluoromethyl- 2-methyl-5-methoxy-indole benzenesulphonyl)-butanesulphonamide114 (4-Amino-2-chloro-5-trifluoromethyl- 2-methyl-6-chloro-indole benzenesulphonyl)-butanesulphonamide115 (4-Amino-2-chloro-5-trifluoromethyl- 1,2-dimethyl-indole benzenesulphonyl)-butanesulphonamide116 (4-Amino-2-chloro-5-trifluoromethyl- 1,2,5-trimethyl-indole benzenesulphonyl)-butanesulphonamide117 (4-Amino-2-chloro-5-trifluoromethyl- 2-methyl-indole benzenesulphonyl)-butanesulphonamide118 (4-Amino-2-chloro-5-trifluoromethyl- 2-phenyl-indole benzenesulphonyl)-butanesulphonamide119 (4-Amino-2-chloro-5-trifluoromethyl- 1-methyl-2-phenyl-indole benzenesulphonyl)-butanesulphonamide120 (4-Amino-2-chloro-5-trifluoromethyl- 2-methyl-indole-sulphonic acid benzenesulphonyl)-butanesulphonamide121 (4-Amino-2,5-dichloro-benzenesulphonyl)- N,N-di-.beta.-hydroxyethyl-3-acetylaminoanilin e benzenesulphonamide122 (4-Amino-2,5-dichloro-benzenesulphonyl)- N-.beta.-cyanoethyl-N-.beta.-hydroxyethyl-3-me thyl- benzenesulphonamide aniline123 (4-Amino-2,5-dichloro-benzenesulphonyl)- N-.beta.-cyanoethyl-N-.beta.-phenylethyl-3-met hyl- benzenesulphonamide aniline124 (4-Amino-2,5-dichloro-benzenesulphonyl)- N-.beta.-cyanoethyl-N-.beta.-acetoxyethyl-3-me thyl- benzenesulphonamide aniline125 (4-Amino-2,5-dichloro-benzenesulphonyl)- N-.beta.-cyanoethyl-2-methoxy-5-acetylamino- benzenesulphonamide aniline126 (4-Amino-2,5-dichloro-benzenesulphonyl)- N,N-diethyl-2-ethoxy-5-(4-toluenesulphonyl)- benzenesulphonamide amino-aniline127 (4-Amino-2,5-dichloro-benzenesulphonyl)- 2-methyl-indole benzenesulphonamide128 (4-Amino-2,5-dichloro-benzenesulphonyl)- 2-phenyl-indole benzenesulphonamide129 (4-Amino-2,5-dichloro-benzenesulphonyl)- 1-methyl-2-phenyl-indole benzenesulphonamide130 (4-Amino-2,5-dichloro-benzenesulphonyl)- 2,5-dimethyl-indole benzenesulphonamide131 (4-Amino-2,5-dichloro-benzenesulphonyl)- 2-methyl-indole-sulphonic acid benzenesulphonamide132 (4-Amino-2,5-dichloro-benzenesulphonyl)- 2-phenyl-indole-sulphonic acid benzenesulphonamide133 (4-Amino-2,5-dichloro-benzenesulphonyl)- 1-methyl-2-phenyl-indole-sulphonic acid benzenesulphonamide134 (4-Amino-2,5-dichloro-benzenesulphonyl)- 1-.beta.-cyanoethyl-3-methyl-5-aminopyrazole benzenesulphonamide135 (4-Amino-2,5-dichloro-benzenesulphonyl)- 1-(4-chlorophenyl)-3-methyl-5-aminopyrazole benzenesulphonamide136 (4-Amino-2,5-dichloro-benzenesulphonyl)- 1-(2,5-dichlorophenyl)-3-methyl-5-amino- benzenesulphonamide pyrazole137 (4-Amino-2,5-dichloro-benzenesulphonyl)- 1-(2-chlorophenyl)-3-ethyl-5-aminopyrazole benzenesulphonamide138 (4-Amino-2,5-dichloro-benzenesulphonyl)- 1-(4-tolyl)-3-methyl-5-aminopyrazole benzenesulphonamide139 (4-Amino-2,5-dichloro-benzenesulphonyl)- N-ethyl-N-.beta.-methoxyethyl-3-methylaniline dimethylaminosulphonamide140 (4-Amino-2,5-dichloro-benzenesulphonyl)- N,N-diethyl-3-methacryloylaminoaniline dimethylaminosulphonamide141 (4-Amino-2,5-dichloro-benzenesulphonyl)- N-cyanoethyl-N-.beta.-acetoxyethyl-3-methyl- dimethylaminosulphonamide aniline142 (4-Amino-2,5-dichloro-benzenesulphonyl)- N,N-diethyl-3-methylaniline dimethylaminosulphonamide143 (4-Amino-2,5-dichloro-benzenesulphonyl)- N-.beta.-cyanoethyl-N-benzyl-3-methylaniline dimethylaminosulphonamide144 (4-Amino-2,5-dichloro-benzenesulphonyl)- N,N-diethyl-3-acetylaminoaniline dimethylaminosulphonamide145 (4-Amino-2,5-dichloro-benzenesulphonyl)- N,N-diethyl-3-formylaminoaniline dimethylaminosulphonamide146 (4-Amino-2,5-dichloro-benzenesulphonyl)- 2-methyl-indole dimethylaminosulphonamide147 (4-Amino-2,5-dichloro-benzenesulphonyl)- 2-phenyl-indole dimethylaminosulphonamide148 (4-Amino-2,5-dichloro-benzenesulphonyl)- 1-methyl-2-phenyl-indole dimethylaminosulphonamide149 (4-Amino-2,5-dichloro-benzenesulphonyl)- 2-methyl-indole-sulphonic acid dimethylaminosulphonamide150 (4-Amino-2,5-dichloro-benzenesulphonyl)- 2-phenyl-indole-sulphonic acid dimethylaminosulphonamide151 (4-Amino-2,5-dichloro-benzenesulphonyl)- 1-cyclohexyl-3-methyl-5-aminopyrazole dimethylaminosulphonamide152 (4-Amino-2,5-dichloro-benzenesulphonyl)- 1-phenyl-3-methyl-5-aminopyrazole dimethylaminosulphonamide153 (4-Amino-2,5-dichloro-benzenesulphonyl)- 1-sec.-butyl-3-methyl-5-aminopyrazole dimethylaminosulphonamide154 (4-Amino-2,5-dichloro-benzenesulphonyl)- 1-.alpha.,.beta.-dimethylpropyl-3-methyl-5-ami no- dimethylaminosulphonamide pyrazole155 (4-Amino-2,5-dichloro-benzenesulphonyl)- 1-benzyl-3-methyl-5-aminopyrazole dimethylaminosulphonamide156 (4-Amino-2,5-dichloro-benzenesulphonyl)- 1-(3-chlorophenyl)-3-ethyl-5-aminopyrazole dimethylaminosulphonamide157 (4-Amino-3-chlorobenzene-sulphonyl)- N,N-diethyl-3-chloroaniline benzenesulphonamide158 (4-Amino-3-chlorobenzene-sulphonyl)- N,N-di-.beta.-hydroxyethyl-3-acetylaminoanilin e benzenesulphonamide159 (4-Amino-3-chlorobenzene-sulphonyl)- N-.beta.-phenylethyl-2-methoxy-5-acetylaminoan iline benzenesulphonamide160 (4-Amino-3-chlorobenzene-sulphonyl)- N,N-di-n-propyl-3-acetylaminoaniline benzenesulphonamide161 (4-Amino-3-chlorobenzene-sulphonyl)- N-ethyl-2-ethoxy-5-acetylaminoaniline benzenesulphonamide162 (4-Amino-3-chloro-benzenesulphonyl)- N-.beta.-cyanoethyl-N-.beta.-phenylethyl-3-met hylaniline benzenesulphonamide163 (4-Amino-3-chloro-benzenesulphonyl)- N-ethyl-N-.beta.-cyanoethyl-3-methylaniline benzenesulphonamide164 (4-Amino-3-chloro-benzenesulphonyl)- N-ethyl-N-.beta.-phenylethyl-3-methylaniline benzenesulphonamide165 (4-Amino-3-chloro-benzenesulphonyl)- N,N-di-n-propylaniline benzenesulphonamide166 (4-Amino-3-chloro-benzenesulphonyl)- N,N-diethyl-3-methylaniline benzenesulphonamide167 (4-Amino-3-chloro-benzenesulphonyl)- N,N-diethylaniline benzenesulphonamide168 (4-Amino-3-chloro-benzenesulphonyl)- 2-methyl-indole benzenesulphonamide169 (4-Amino-3-chloro-benzenesulphonyl)- 2-phenyl-indole benzenesulphonamide170 (4-Amino-3-chloro-benzenesulphonyl)- 1-methyl-2-phenyl-indole benzenesulphonamide171 (4-Amino-3-chloro-benzenesulphonyl)- 1,2-dimethyl-indole benzenesulphonamide172 (4-Amino-3-chloro-benzenesulphonyl)- 2-.beta.-naphthyl-indole benzenesulphonamide173 (4-Amino-3-chloro-benzenesulphonyl)- 2-p-diphenylyl-indole benzenesulphonamide174 (4-Amino-3-chloro-benzenesulphonyl)- 1,2,5-trimethyl-indole benzenesulphonamide175 (4-Amino-3-chloro-benzenesulphonyl)- 1-ethyl-2-methyl-indole benzenesulphonamide176 (4-Amino-3-chloro-benzenesulphonyl)- 2-methyl-6-chloro-indole benzenesulphonamide177 (4-Amino-3-chloro-benzenesulphonyl)- 2-methyl-7-chloro-indole benzenesulphonamide178 (4-Amino-3-chloro-benzenesulphonyl)- 2-methyl-5,7-dichloro-indole benzenesulphonamide179 (4-Amino-3-chloro-benzenesulphonyl)- 1,2-dimethyl-indole-sulphonic acid benzenesulphonamide180 (4-Amino-3-chloro-benzenesulphonyl)- 2-methyl-indole-sulphonic acid benzenesulphonamide181 (4-Amino-3-chloro-benzene-sulphonyl)- 2-phenyl-indole-sulphonic acid benzenesulphonamide182 (4-Amino-3-chloro-benzenesulphonyl)- 1-methyl-2-phenyl-indole-sulphonic acid benzenesulphonamide183 (4-Amino-3-chloro-benzenesulphonyl)- 1-ethyl-2-phenyl-indole-sulphonic acid benzenesulphonamide184 (4-Amino-3-chloro-benzenesulphonyl)- 1,2,5-trimethyl-indole-sulphonic acid benzenesulphonamide185 (4-Amino-3-chloro-benzenesulphonyl)- 1-ethyl-2-methyl-indole-sulphonic acid benzenesulphonamide186 (4-Amino-3-chloro-benzenesulphonyl)- 1-(3-nitrophenyl)-3-methyl-5-aminopyrazole benzenesulphonamide187 (4-Amino-3-chloro-benzenesulphonyl)- 1-isopropyl-3-methyl-5-aminopyrazole benzenesulphonamide188 (4-Amino-3-chloro-benzenesulphonyl)- 1-.beta.-hydroxyethyl-3-methyl-5-aminopyrazole benzenesulphonamide189 (4-Amino-3-chloro-benzenesulphonyl)- 1,3-dimethyl-5-aminopyrazole benzenesulphonamide190 (4-Amino-3-chloro-benzenesulphonyl)- 1-ethyl-3-methyl-5-aminopyrazole benzenesulphonamide191 (4-Amino-3-chloro-benzenesulphonyl)- 1-.beta.-cyanoethyl-3-methyl-5-aminopyrazole192 (4-Amino-3-chloro-benzenesulphonyl)- 1-cyclohexyl-3-methyl-5-aminopyrazole benzenesulphonamide193 (4-Amino-3-chloro-benzenesulphonyl)- 1-phenyl-3-methyl-5-aminopyrazole benzenesulphonamide194 (4-Amino-3-chloro-benzenesulphonyl)- 3-methyl-5-aminopyrazole benzenesulphonamide195 (4-Amino-3-chloro-benzenesulphonyl)- 1-(.alpha.-phenylethyl)-3-methyl-5-aminopyrazo le benzenesulphonamide196 (4-Amino-3-chloro-benzenesulponyl)- 1-(3-chlorophenyl)-3-methyl-5-aminopyrazole benzenesulphonamide197 (4-Amino-3-chloro-benzenesulphonyl)- 1-(2-chlorophenyl)-3-methyl-5-aminopyrazole benzenesulphonamide198 (4-Amino-3-chloro-benzenesulphonyl)- 1-(2-trifluoromethylphenyl)-3-methyl-5-amino- benzenesulphonamide pyrazole199 (4-Amino-3-chloro-benzenesulphonyl)- N,N-diethyl-3-methylaniline p-toluenesulphonamide200 (4-Amino-3-chloro-benzenesulphonyl)- N-ethyl-N-.beta.-phenylethyl-3-methylaniline p-toluenesulphonamide201 (4-Amino-3-chloro-benzenesulphonyl)- N,N-diethylaniline p-toluenesulphonamide202 (4-Amino-3-chloro-benzenesulphonyl)- N,N-dipropyl-3-methylaniline p-toluenesulphonamide203 (4-Amino-3-chloro-benzenesulphonyl)- N-ethyl-2,5-dimethylaniline p-toluenesulphonamide204 (4-Amino-3-chloro-benzenesulphonyl)- N,N-di-.beta.-hydroxyethyl-3-benzoylaminoanili ne p-toluenesulphonamide205 (4-Amino-3-chloro-benzenesulphonyl)- N-.beta.-cyanoethyl-3-acetylaminoaniline p-toluenesulphonamide206 (4-Amino-3-chloro-benzenesulphonyl)- N-ethyl-N-.beta.-ethoxycarbonyloxyethyl-3-meth yl- p-toluenesulphonamide aniline207 (4-Amino-3-chloro-benzenesulphonyl)- N-.beta.-hydroxyethyl-2-methoxy-5-methylanilin e p-toluenesulphonamide208 (4-Amino-3-chloro-benzenesulphonyl)- N,N-di-.beta.-ethoxyethyl-3-acetylaminoaniline p-toluenesulphonamide209 (4-Amino-3-chloro-benzenesulphonyl)- N-ethyl-N-.beta.-methoxycarbonylethyl-3-methyl aniline p-toluenesulphonamide210 (4-Amino-3-chloro-benzenesulphonyl)- N-ethyl-N-.beta.-methoxycarbonyloxyethyl-3-ace tyl- p-toluenesulphonamide aminoaniline211 (4-Amino-3-chloro-benzenesulphonyl)- N-ethyl-N-.beta.-hydroxyethyl-3-methylaniline p-toluenesulphonamide212 (4-Amino-3-chloro-benzenesulphonyl)- N-ethyl-N-.beta.-cyanoethyl-3-methylaniline p-toluenesulphonamide213 (4-Amino-3-chloro-benzenesulphonyl)- 2-methyl-indole-sulphonic acid p-toluenesulphonamide214 (4-Amino-3-chloro-benzenesulphonyl)- 2-phenyl-indole-sulphonic acid p-toluenesulphonamide215 (4-Amino-3-chloro-benzenesulphonyl)- 1-methyl-2-phenyl-indole-sulphonic acid p-toluenesulphonamide216 (4-Amino-3-chloro-benzenesulphonyl)- 2-methyl-indole p-toluenesulphonamide217 (4-Amino-3-chloro-benzenesulphonyl)- 2-phenyl-indole p-toluenesulphonamide218 (4-Amino-3-chloro-benzenesulphonyl)- 1-methyl-2-phenyl-indole p-toluenesulphonamide219 (4-Amino-3-chloro-benzenesulphonyl)- 1,2,5-trimethyl-indole p-toluenesulphonamide220 (4-Amino-3-chloro-benzenesulphonyl)- 1,2,6-trimethyl-indole-sulphonic acid p-toluenesulphonamide221 (4-Amino-3-chloro-benzenesulphonyl)- 1,5-dimethyl-2-phenyl-indole-sulphonic acid p-toluenesulphonamide222 (4-Amino-3-chloro-benzenesulphonyl)- 1-ethyl-2-methyl-indole p-toluenesulphonamide223 (4-Amino-3-chloro-benzenesulphonyl)- 1-ethyl-2-phenyl-indole p-toluenesulphonamide224 (4-Amino-3-chloro-benzenesulphonyl)- 2-methyl-6-chloro-indole p-toluenesulphonamide225 (4-Amino-3-chloro-benzenesulphonyl)- 2-methyl-5-methoxy-indole p-toluenesulphonamide226 (4-Amino-3-chloro-benzenesulphonyl)- 1-n-butyl-2-methyl-indole p-toluenesulphonamide227 (4-Amino-3-chloro-benzenesulphonyl)- 2-methyl-7-chloro-indole p-toluenesulphonamide228 (4-Amino-3-chloro-benzenesulphonyl)- 2-methyl-5,7-dichloro-indole p-toluenesulphonamide229 (4-Amino-3-chloro-benzenesulphonyl)- 2-methyl-5-fluoro-indole p-toluenesulphonamide230 (4-Amino-3-chloro-benzenesulphonyl)- 1-phenyl-3-methyl-5-aminopyrazole p-toluenesulphonamide231 (4-Amino-3-chloro-benzenesulphonyl)- 1-(2-chlorophenyl)-3-methyl-5-aminopyrazole p-toluenesulphonamide232 (4-Amino-3-chloro-benzenesulphonyl)- 1-(2-trifluorophenyl)-3-methyl-5-aminopyrazole p-toluenesulphonamide233 (4-Amino-3-chloro-benzenesulphonyl)- 1-phenyl-3-ethyl-5-aminopyrazole p-toluenesulphonamide234 (4-Amino-3-chloro-benzenesulphonyl)- 1-(4-tolyl)-3-methyl-5-aminopyrazole p-toluenesulphonamide235 (4-Amino-3-chloro-benzenesulphonyl)- 1-cyclohexyl-3-methyl-5-aminopyrazole p-toluenesulphonamide236 (4-Amino-3-chloro-benzenesulphonyl)- 1-cyclopentyl-3-methyl-5-aminopyrazole p-toluenesulphonamide237 (4-Amino-3-bromo-benzenesulphonyl)- N,N-diethyl-3-methylaniline benzenesulphonamide238 (4-Amino-3-bromo-benzenesulphonyl)- N-ethyl-N-benzylaniline benzenesulphonamide239 (4-Amino-3-bromo-benzenesulphonyl)- 2-methyl-indole benzenesulphonamide240 (4-Amino-3-bromo-benzenesulphonyl)- 2-phenyl-indole-sulphonic acid benzenesulphonamide241 (4-Amino-3-bromo-benzenesulphonyl)- 1-(4-tolyl)-3-methyl-5-aminopyrazole benzenesulphonamide242 (4-Amino-3-bromo-benzenesulphonyl)- 1-cyclohexyl-3-methyl-5-aminopyrazole benzenesulphonamide243 (4-Amino-3-bromo-benzenesulphonyl)- N-ethyl-N-benzyl-3-methylaniline butanesulphonamide244 (4-Amino-3-bromo-benzenesulphonyl)- N-ethyl-N-.beta.-cyanoethyl-3-methylaniline butanesulphonamide245 (4-Amino-3-bromo-benzenesulphonyl)- 2-phenyl-indole butanesulphomamide246 (4-Amino-3-bromo-benzenesulphonyl)- 1-methyl-2-phenyl-indole butanesulphonamide247 (4-Amino-3-bromo-benzenesulphonyl)- 2-methyl-7-chloro-indole butanesulphonamide248 (4-Amino-3-bromo-benzenesulphonyl)- 2-methyl-indole-sulphonic acid butanesulphonamide249 (4-Amino-3-methyl-benzenesulphonyl)- N,N-diethyl-3-acetylaminoaniline p-toluenesulphonamide250 (4-Amino-3-methyl-benzenesulphonyl)- N-ethyl-N-.beta.-hydroxyethyl-3-methylaniline p-toluenesulphonamide251 (4-Amino-3-methyl-benzenesulphonyl)- 2-methyl-indole p-toluenesulphonamide252 (4-Amino-3-methyl-benzenesulphonyl)- 2-methyl-5,7-dichloro-indole p-toluenesulphonamide253 (4-Amino-3-methyl-benzenesulphonyl)- 2-phenyl-indole p-toluenesulphonamide254 (4-Amino-3-methyl-benzenesulphonyl)- 1-phenyl-3-methyl-5-aminopyrazole p-toluenesulphonamide255 (4-Amino-3-methyl-benzenesulphonyl)- 1-(2-chlorophenyl)-3-methyl-5-aminopyrazole p-toluenesulphonamide256 (4-Amino-3-methyl-benzenesulphonyl)- N-ethyl-N-.beta.-phenylethyl-3-methylaniline butanesulphonamide257 (4-Amino-3-methyl-benzenesulphonyl)- N,N-diethylaniline butanesulphonamide258 (4-Amino-3-methyl-benzenesulphonyl)- 1-methyl-2-phenyl-indole butanesulphonamide259 (4-Amino-3-methyl-benzenesulphonyl)- 2-phenyl-indole butanesulphonamide260 (4-Amino-3-methyl-benzenesulphonyl)- 1-(2-trifluoromethylphenyl)-3-methyl-5-amino- butanesulphonamide pyrazole261 (4-Amino-2-trifluoromethyl-benzene- N-.beta.-cyanoethyl-N-benzyl-3-methylaniline sulphonyl)-o-toluenesulphonamide262 (4-Amino-2-trifluoromethyl-benzene- N,N-di-n-propyl-3-methylaniline sulphonyl)-o-toluenesulphonamide263 (4-Amino-2-trifluoromethyl-benzene- N-.beta.-cyanoethyl-3-benzoylaminoaniline sulphonyl)-o-toluenesulphonamide264 (4-Amino-2-trifluoromethyl-benzene- 2-methyl-indole sulphonyl)-o-toluenesulphonamide265 (4-Amino-2-trifluoromethyl-benzene- 2-phenyl-indole sulphonyl)-o-toluenesulphonamide266 (4-Amino-2-trifluoromethyl-benzene- 1-phenyl-3-ethyl-5-aminopyrazole sulphonyl)-o-toluenesulphonamide267 (4-Amino-2-trifluoromethyl-benzene- N-.beta.-cyanoethyl-N-.beta.-phenylethyl-3-met hylaniline sulphonyl)-2-naphthylsulphonamide268 (4-Amino-2-trifluoromethyl-benzene- N-n-butyl-N-benzyl-3-methylaniline sulphonyl)-2-naphthylsulphonamide269 (4-Amino-2-trifluoromethyl-benzene- N,N-diethyl-3-methoxyaniline sulphonyl)-2-naphthylsulphonamide270 (4-Amino-2-trifluoromethyl-benzene- 2-phenyl-indole sulphonyl)-2-naphthylsulphonamide271 (4-Amino-2-trifluoromethyl-benzene- 2-methyl-indole sulphonyl)-2-naphthylsulphonamide272 (4-Amino-2-trifluoromethyl-5-chloro- N-ethyl-N-.beta.-hydroxyethyl-3-methylaniline benzenesulphonyl)-benzenesulphonamide273 (4-Amino-2-trifluoromethyl-5-chloro- N,N-di-.beta.-hydroxyethyl-3-acetylaminoanilin e benzenesulphonyl)-benzenesulphonamide274 (4-Amino-2-trifluoromethyl-5-chloro- N-ethyl-N-benzyl-3-ethylaniline benzenesulphonyl)-benzenesulphonamide275 (4-Amino-2-trifluoromethyl-5-chloro- N,N-diethyl-3-ethoxyaniline benzenesulphonyl)-benzenesulphonamide276 (4-Amino-2-trifluoromethyl-5-chloro- N-ethyl-2,5-dimethylaniline benzenesulphonyl)-benzenesulphonamide277 (4-Amino-2-trifluoromethyl-5-chloro- N-.beta.-cyanoethyl-2-methoxy-5-methylaniline benzenesulphonyl)-benzenesulphonamide278 (4-Amino-2-trifluoromethyl-5-chloro- 1-ethyl-2-phenyl-indole benzenesulphonyl)-benzenesulphonamide279 (4-Amino-2-trifluoromethyl-5-chloro- 2-ethyl-indole benzenesulphonyl)-benzenesulphonamide280 (4-Amino-2-trifluoromethyl-5-chloro- 2-methyl-indole benzenesulphonyl)-benzenesulphonamide281 (4-Amino-2-trifluoromethyl-5-chloro- 1-methyl-2-phenyl-indole-sulphonic acid benzenesulphonyl)-benzenesulphonamide282 (4-Amino-2-trifluoromethyl-5-chloro- 2-methyl-6-chloro-indole benzenesulphonyl)-benzenesulphonamide283 (4-Amino-2-trifluoromethyl-5-chloro- N,N-diethyl-3-methylaniline benzenesulphonyl)-ethanesulphonamide284 (4-Amino-2-trifluoromethyl-5-chloro- N-ethyl-3-acetylaminoaniline benzenesulphonyl)-ethanesulphonamide285 (4-Amino-2-trifluoromethyl-5-chloro- 2-methyl-indole benzenesulphonyl)-ethanesulphonamide286 (4-Amino-2-trifluoromethyl-5-chloro- 2-phenyl-indole benzenesulphonyl)-ethanesulphonamide287 (4-Amino-2-trifluoromethyl-5-chloro- 1-(2-5-dichlorophenyl)-3-methyl-5-aminopyrazol e benzenesulphonyl)-ethanesulphonamide288 (4-Amino-2-trifluoromethyl-5-chloro- 1-(2-chlorophenyl)-3-ethyl-5-aminopyrazole benzenesulphonyl)-ethanesulphonamide289 (4-Amino-2-trifluoromethyl-5-chloro- 1-(4-tolyl)-3-methyl-5-aminopyrazole benzenesulphonyl)-ethanesulphonamide290 (4-Amino-2-trifluoromethyl-5-bromo- N,N-di-.beta.-methoxyethyl-3-methylaniline benzenesulphonyl)-p-toluenesulphonamide291 (4-Amino-2-trifluoromethyl-5-bromo- N,N-diethyl-3-formylaminoaniline benzenesulphonyl)-p-toluenesulphonamide292 (4-Amino-2-trifluoromethyl-5-bromo- 2-methyl-indole benzenesulphonyl)-p-toluenesulphonamide293 (4-Amino-2-trifluoromethyl-5-bromo- 2-phenyl-indole benzenesulphonyl)-p-toluenesulphonamide294 (4-Amino-2-trifluoromethyl-5-bromo- N,N-diethyl-3-acetylaminoaniline benzenesulphonyl)-benzenesulphonamide295 (4-Amino-2-trifluoromethyl-5-bromo- N-.beta.-cyanoethyl-N-.beta.-acetoxyethyl-3-me thylaniline benzenesulphonyl)-benzenesulphonamide296 (4-Amino-2-trifluoromethyl-5-bromo- N,N-diethyl-3-benzoylaminoaniline benzenesulphonyl)-benzenesulphonamide297 (4-Amino-2-trifluoromethyl-5-bromo- N-n-butyl-N-benzyl-3-methylaniline benzenesulphonyl)-benzenesulphonamide298 (4-Amino-2-trifluoromethyl-5-bromo- 2-methyl-indole benzenesulphonyl)-benzenesulphonamide299 (4-Amino-2-trifluoromethyl-5-bromo- 2-phenyl-indole benzenesulphonyl)-benzenesulphonamide300 (4-Amino-2-trifluoromethyl-5-bromo- 2-phenyl-indole-sulphonic acid benzenesulphonyl)-benzenesulphonamide301 (4-Amino-2-trifluoromethyl-5-bromo- 1-cyclohexyl-3-methyl-5-aminopyrazole benzenesulphonyl)-benzenesulphonamide302 (4-Amino-2-trifluoromethyl-5-bromo- 1-phenyl-3-methyl-5-aminopyrazole benzenesulphonyl)-benzenesulphonamide303 (4-Amino-2-trifluoromethyl-5-bromo- 1-(2-trifluoromethylphenyl)-3-methyl-5-amino- benzenesulphonyl)-benzenesulphonamide pyrazole304 (4-Amino-2,5-dibromo-benzenesulphonyl)- N,N-di-n-propyl-3-methylaniline o-toluenesulphonamide305 (4-Amino-2,5-dibromo-benzenesulphonyl)- N,N-diethyl-3-propionylaminoaniline o-toluenesulphonamide306 (4-Amino-2,5-dibromo-benzenesulphonyl)- N-ethyl-N-benzyl-3-methylaniline o-toluenesulphonamide307 (4-Amino-2,5-dibromo-benzenesulphonyl)- N,N-diethyl-3-n-propoxyaniline o-toluenesulphonamide308 (4-Amino-2,5-dibromo-benzenesulphonyl)- N-.beta.-cyanoethyl-2-chloroaniline o-toluenesulphonamide309 (4-Amino-2,5-dibromo-benzenesulphonyl)- N-ethyl-N-.beta.-ethoxyethyl-3-methylaniline o-toluenesulphonamide310 (4-Amino-2,5-dibromo-benzenesulphonyl)- 2-methyl-indole o-toluenesulphonamide311 (4-Amino-2,5-dibromo-benzenesulphonyl)- 1-methyl-2-phenyl-indole o-toluenesulphonamide312 (4-Amino-2,5-dibromo-benzenesulphonyl)- 1,2-dimethyl-indole o-toluenesulphonamide313 (4-Amino-2,5-dibromo-benzenesulphonyl)- 1,2,5-trimethyl-indole o-toluenesulphonamide314 (4-Amino-2,5-dibromo-benzenesulphonyl)- 1-benzyl-3-methyl-5-aminopyrazole o-toluenesulphonamide315 (4-Amino-2,5-dibromo-benzenesulphonyl)- 1-(3-chlorophenyl)-3-ethyl-5-aminopyrazole o-toluenesulphonamide316 (4-Amino-2,5-dibromo-benzenesulphonyl)- 1-cyclohexyl-3-methyl-5-aminopyrazole o-toluenesulphonamide317 (4-Amino-2,5-dibromo-benzenesulphonyl)- 1-phenyl-3-methyl-5-aminopyrazole o-toluenesulphonamide318 (4-Amino-2,5-dibromo-benzenesulphonyl)- 3-methyl-5-aminopyrazole o-toluenesulphonamide319 (4-Amino-3,5-dichlorobenzenesulphonyl)- N,N-diethyl-3-methylaniline p-toluenesulphonamide320 (4-Amino-3,5-dichlorobenzenesulphonyl)- N,N-di-n-propylaniline p-toluenesulphonamide321 (4-Amino-3,5-dichlorobenzenesulphonyl)- 1-.alpha.-phenylethyl-3-methyl-5-aminopyrazole p-toluenesulphonamide322 (4-Amino-3,5-dichlorobenzenesulphonyl)- 1-phenyl-3-methyl-5-aminopyrazole p-toluenesulphonamide323 (4-Amino-2,5-dimethylbenzenesulphonyl)- N,N-diethyl-3-methylaniline benzenesulphonamide324 (4-Amino-2,5-dimethylbenzenesulphonyl)- N-ethyl-N-.beta.-methoxycarbonylethyl-3-methyl aniline benzenesulphonamide325 (4-Amino-2,5-dimethylbenzenesulphonyl)- N,N-diethyl-3-butyrylaminoaniline benzenesulphonamide326 (4-Amino-2,5-dimethylbenzenesulphonyl)- 2-methyl-indole benzenesulphonamide327 (4-Amino-2,5-dimethylbenzenesulphonyl)- 1-methyl-2-phenyl-indole benzenesulphonamide328 (4-Amino-2,5-dimethylbenzenesulphonyl)- 1-ethyl-2-methyl-indole benzenesulphonamide329 (4-Amino-2,5-dimethylbenzenesulphonyl)- 2-phenyl-indole-sulphonic acid benzenesulphonamide330 (4-Amino-2,5-dimethylbenzenesulphonyl)- 2-methyl-indole-sulphonic acid benzenesulphonamide331 (4-Amino-2,5-dimethylbenzenesulphonyl)- N-ethyl-N-benzyl-3-methylaniline dimethylaminosulphonamide332 (4-Amino-2,5-dimethylbenzenesulphonyl)- N,N-diethyl-3-(4-chlorobenzoyl)-aminoaniline dimethylaminosulphonamide333 (4-Amino-2,5-dimethylbenzenesulphonyl)- 2-methyl-indole dimethylaminosulphonamide334 (4-Amino-2-methyl-5-trifluoromethyl- N,N-diethyl-3-phenacetylaminoaniline benzenesulphonyl)-p-toluenesulphonamide335 (4-Amino-2-methyl-5-trifluoromethyl- N,N-diethyl-3-methyl benzenesulphonyl)-p-toluenesulphonamide336 (4-Amino-2-methyl-5-trifluoromethyl- 2-methyl-indole benzenesulphonyl)-p-toluenesulphonamide337 (4-Amino-2-methyl-5-trifluoromethyl- 2-phenyl-indole benzenesulphonyl)-p-toluenesulphonamide338 (4-Amino-2-methyl-5-trifluoromethyl- 1-methyl-2-phenyl-indole benzenesulphonyl)-p-toluenesulphonamide339 (4-Amino-2-methyl-5-trifluoromethyl- N-ethyl-N-.beta.-ethoxycarbonyloxyethyl-3-meth ylaniline benzenesulphonyl)-p-toluenesulphonamide340 (4-Amino-2-methyl-5-trifluoromethyl- 1-(2-chlorophenyl)-3-methyl-5-aminopyrazole benzenesulphonyl)-p-toluenesulphonamide341 (4-Amino-2-methyl-5-trifluoromethyl- 1-(2-trifluoromethyl)-3-methyl-5-aminopyrazole benzenesulphonyl)-p-toluenesulphonamide342 (4-Amino-2-methyl-5-trifluoromethyl- 1-phenyl-3-methyl-5-aminopyrazole benzenesulphonyl)-p-toluenesulphonamide343 (4-Amino-2-methyl-5-chloro-benzene- N-ethyl-N-.beta.-hydroxyethyl-3-methylaniline sulphonyl)-benzenesulphonamide344 (4-Amino-2-methyl-5-chloro-benzene- N,N-diethyl-3-methylaniline sulphonyl)-benzenesulphonamide345 (4-Amino-2-methyl-5-chloro-benzene- N,N-di-.beta.-hydroxyethyl-3-acetylaminoanilin e sulphonyl)-benzenesulphonamide346 (4-Amino-2-methyl-5-chloro-benzene- 2-methyl-indole sulphonyl)-benzenesulphonamide347 (4-Amino-2-methyl-5-chloro-benzene- 2-phenyl-indole sulphonyl)-benzenesulphonamide348 (4-Amino-2-methyl-5-chloro-benzene- 2-phenyl-indole-sulphonic acid sulphonyl)-benzenesulphonamide349 (4-Amino-2-methyl-5-chloro-benzene- 2-methyl-indole-sulphonic acid sulphonyl)-benzenesulphonamide350 (4-Amino-2-methyl-5-chloro-benzene- 1-phenyl-3-methyl-5-aminopyrazole sulphonyl)-benzenesulphonamide351 (4-Amino-2-methyl-5-chloro-benzene- 1-(2-chlorophenyl)-3-methyl-5-aminopyrazole sulphonyl)-benzenesulphonamide352 (4-Amino-2-methyl-5-chloro-benzene- 1-(4-tolyl)-3-methyl-5-aminopyrazole sulphonyl)-benzenesulphonamide353 (4-Amino-2-methyl-5-chlorobenzene- 1-(3-chlorophenyl)-3-methyl-5-aminopyrazole sulphonyl)-p-toluenesulphonamide354 (4-Amino-2-methyl-5-chlorobenzene- 1-(4-chlorophenyl)-3-methyl-5-aminopyrazole sulphonyl)-p-toluenesulphonamide355 (3-Amino-4-chlorobenzenesulphonyl)- 2-methyl-indole methanesulphonamide356 (3-Amino-4-chlorobenzenesulphonyl)- 2-phenyl-indole methanesulphonamide357 (3-Amino-4-chlorobenzenesulphonyl)- 1-phenyl-3-methyl-5-aminopyrazole methanesulphonamide358 (3-Amino-4-chlorobenzenesulphonyl)- N,N-diethyl-3-methylaniline methanesulphonamide359 (3-Amino-6-chlorobenzenesulphonyl)- 1-methyl-2-phenyl-indole benzenesulphonamide360 (3-Amino-6-chlorobenzenesulphonyl)- 2-methyl-indole benzenesulphonamide361 (3-Amino-6-chlorobenzenesulphonyl)- 1,2-dimethyl-indole benzenesulphonamide362 (3-Amino-6-chlorobenzenesulphonyl)- 1-(4-chlorophenyl)-3-methyl-5-aminopyrazole benzenesulphonamide363 (3-Amino-benzenesulphonyl)-p-toluene- 2-methyl-indole sulphonamide364 (3-Amino-benzenesulphonyl)-p-toluene- 2-phenyl-indole sulphonamide365 (3-Amino-benzenesulphonyl)-p-toluene- 1-(2-trifluoromethylphenyl)-3-methyl-5-amino- sulphonamide pyrazole366 (3-Amino-4-methyl-benzenesulphonyl)- N,N-diethyl-3-methylaniline butanesulphonamide367 (3-Amino-4-methyl-benzenesulphonyl)- 2-methyl-indole butanesulphonamide368 (3-Amino-4-methyl-benzenesulphonyl)- 1,2-dimethyl-indole butanesulphonamide369 (3-Amino-6-methyl-benzenesulphonyl)- 2-methyl-indole benzenesulphonamide370 (3-Amino-6-methyl-benzenesulphonyl)- 2-phenyl-indole benzenesulphonamide371 (3-Amino-6-methyl-benzenesulphonyl)- 1-methyl-2-phenyl-indole benzenesulphonamide372 (3-Amino-4-methoxy-benzenesulphonyl)- N,N-diethyl-3-methylaniline p-toluenesulphonamide373 (3-Amino-6-ethyl-benzenesulphonyl)- N,N-diethyl-3-acetylaminoaniline o-toluenesulphonamide374 (3-Amino-6-ethyl-benzenesulphonyl)- N-ethyl-N-.beta.-hydroxyethyl-3-methylaniline o-toluenesulphonamide375 (3-Amino-6-ethyl-benzenesulphonyl)- 2-methyl-indole o-toluenesulphonamide376 (3-Amino-6-ethyl-benzenesulphonyl)- 1-phenyl-3-methyl-5-aminopyrazole o-toluenesulphonamide377 (3-Amino-benzenesulphonyl)-benzene- 2-methyl-indole sulphonamide378 (3-Amino-benzenesulphonyl)-benzene- 2-phenyl-indloe-sulphonic acid sulphonamide379 (3-Amino-4-chloro-5-methyl-benzene- N-ethyl-N-.beta.-phenylethyl-3-methylaniline sulphonyl)-butanesulphonamide380 (3-Amino-4-chloro-5-methyl-benzene- 2-methyl-indole sulphonyl)-butanesulphonamide381 (3-Amino-4-chloro-5-methyl-benzene- 2-phenyl-indole sulphonyl)-butanesulphonamide382 (3-Amino-4-chloro-5-methyl-benzene- 1,2-dimethyl-indole sulphonyl)-butanesulphonamide383 (3-Amino-4-chloro-5-methyl-benzene- 1-phenyl-3-methyl-5-aminopyrazole sulphonyl)-butanesulphonamide384 (4-Amino-benzenesulphonyl)-2-naphthyl- N,N-diethyl-3-methylaniline sulphonamide385 (4-Amino-benzenesulphonyl)-2-naphthyl- 2-methyl-indole sulphonamide386 (2-Amino-3-chloro-4-methoxy-benzene- 2-methyl-indole sulphonyl)-benzenesulphonamide387 (2-Amino-3-chloro-4-methoxy-benzene- 2-phenyl-indole sulphonyl)-benzenesulphonamide388 (2-Amino-benzenesulphonyl)-p-toluene- N,N-diethyl-3-acetylaminoaniline sulphonamide389 (2-Amino-benzenesulphonyl)-p-toluene- 2-methyl-indole sulphonamide390 (2-Amino-benzenesulphonyl)-p-toluene- 2-phenyl-indole sulphonamide391 (2-Amino-benzenesulphonyl)-p-toluene- 1-(4-chlorophenyl)-3-methyl-5-aminopyrazole392 (2-Amino-benzenesulphonyl)-p-toluene- 1-(2-trifluoromethylphenyl)-3-methyl-5-aminopy ra- sulphonamide zole393 (3-Amino-4-trifluoromethyl-benzene- N,N-diethyl-3-methylaniline sulphonyl)-benzenesulphonamide394 (3-Amino-4-trifluoromethyl-benzene- 2-methyl-indole sulphonyl)-benzenesulphonamide395 (3-Amino-4-trifluoromethyl-benzene- 2-phenyl-indole sulphonyl)-benzenesulphonamide396 (3-Amino-4-trifluoromethyl-benzene- 2-methyl-7-chloro-indole sulphonyl)-benzenesulphonamide397 (3-Amino-4-trifluoromethyl-benzene- 2,5-dimethyl-indole sulphonyl)-benzenesulphonamide398 (3-Amino-4-trifluoromethyl-benzene- 1-.beta.-cyanoethyl-3-methyl-5-aminopyrazole sulphonyl)-benzenesulphonamide399 (3-Amino-4-trifluoromethyl-benzene- 1-phenyl-3-methyl-5-aminopyrazole sulphonyl)-benzenesulphonamide400 (3-Amino-4-trifluoromethyl-benzene- 1-(2-trifluoromethylphenyl)-3-methyl-5-amino- sulphonyl)-benzenesulphonamide pyrazole401 (3-Amino-4-trifluoromethyl-benzene- 1-(4-chlorophenyl)-3-methyl-5-aminopyrazole sulphonyl)-benzenesulphonamide402 (4-Amino-2,5-bis-(trifluoromethyl)-benzene- 2-methyl-indole sulfonyl)-benzenesulfonamid403 (4-Amino-2,5-bis-(trifluoromethyl)-benzene- 2-phenyl-indole sulfonyl)-benzenesulfonamid404 (4-Amino-2,5-bis-(trifluoromethyl)-benzene- N,N-diethyl-3-methylaniline sulfonyl)-benzenesulfonamid405 (4-Amino-3,5-bis-(trifluoromethyl)-benzene- 2-methyl-indole sulfonyl)-p-chlor-benzenesulfonamide406 (4-Amino-3,5-bis-(trifluoromethyl)-benzene- 1-methyl-2-phenyl-indole sulfonyl)-p-chlor-benzenesulfonamide407 (4-Amino-2,5-bis-(trifluoromethyl)-benzene- 2-methyl-indole sulfonyl-p-toluenesulfonamid408 (4-Amino-2,5-bis-(trifluoromethyl)-benzene- N-ethyl-N-.beta.-cyano-ethyl- sulfonyl-p-toluenesulfonamid 3-methyl-aniline__________________________________________________________________________

Claims

1. Monoazo dyestuff having the formula ##STR24## in which R.sub.1 is phenyl; naphthyl; phenyl substituted with alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, halogen, cyano or nitro; alkyl of 1-4 carbon atoms; or dialkylamino in which the alkyl groups contain 1-4 carbon atoms;

R.sub.3 is hydrogen, halogen, alkyl with 1-4 carbon atoms; alkoxy with 1-4 carbon atoms or trifluoromethyl;

R.sub.4 is alkyl of 1-4 carbon atoms; phenyl; naphthyl; or phenyl or naphthyl substituted by halogen, alkyl of 1-4 carbon atoms or phenyl;

R.sub.5 is hydrogen or unsubstituted alkyl with 1-4 carbon atoms; and

R.sub.6 is hydrogen, cyano, halogen, alkyl with 1-4 carbon atoms or alkoxy with 1-4 carbon atoms.

2. Monoazo dyestuff of claim 1 in which R.sub.4 is alkyl of 1-4 carbon atoms; phenyl; or phenyl substituted by halogen, alkyl of 1-4 carbon atoms or phenyl; and

R.sub.6 is hydrogen, halogen or alkyl with 1-4 carbon atoms.

3. Monoazo dyestuff of claim 1 having the formula ##STR25##

4. Monoazo dyestuff of claim 1 having the formula ##STR26##