Ciba-geigy Corporation

Jean-Jacques Gallay

Paul Brenneisen

Alfred Meyer

Manfred Kuhne

Ernst Aufderhaar

Max Schellenbaum

Wolfgang Schmid

Ernst Schweizer

Rene Bosshard

Peter Labuhn

Oswald Rechsteiner

Thomas Wenger

The invention relates to a process for the manufacture of novel benzazole derivatives of the formula I ##STR1## in which R.sub.1 represents an optionally 4-substituted piperazino group or a group of the formula R.sub.2 --alk--X.sub.2 --,

Process for the manufacture of novel benzazole derivatives,

Benzimidazole derivatives of the formula ##STR1## in which R is an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, an alkynyl group having 3 to 5 carbon atoms or a benzyl group, which is unsubstituted or monosubstituted to disubstituted by a methyl group, halogen or a nitro group;

2-Alkylthio-, 2-alkylsulphinyl- and

A new process for the production of 3,4-dialkoxyanilines in which the two alkyl groups are different from each other is disclosed. The process comprises the stepwise introduction of the alkyl groups in different stages of the process by converting pyrocatechol into its monoalkyl ether, coupling said monoalkyl ether with a phenyldiazonium salt, alkylating the 3-alkoxy-4-hydroxy-azobenzene obtained to form 3,4-dialkoxyazobenzene and reductively cleaving the latter to the corresponding 3,4-dialkoxyaniline. The 3,4-dialkoxyanilines obtainable by the new process are valuable intermediates for the preparation of 4-hydroxy-6,7-dialkoxy-3-quinoline carboxylic acid esters which are excellent coccidiostats.

Process for the preparation of 3,4-dialkoxyanilines

Isothiocyano substituted 2-phenoxy, 2-phenylthio and 2-phenylamino-benzoxazoles have anthelmintic activity in warm-blooded animals. Included are compounds of the formula ##SPC1## In which one of R.sub.2 and R.sub.5 is isothiocyano and the other is hydrogen, methyl, methoxy, chlorine or nitro; Y is oxygen, sulphur or ##EQU1## wherein R is hydrogen or methyl; and n is 0 or 1.

2-Phenoxy, -phenylthio-, and -phenyl-amino-benzoxazoles having an

Isothiocyanobenzazoles of the formula ##SPC1## Wherein

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Magden, Switzerland

Jean-Jacques Gallay