1) Application of 2, 4-dichloronitrobenzene to the potassium salts 2, 5-dichloro-, 2, 4, 5-trichloro-, p-fluoro-, and p-iodophenols, and p-chlorothiophenol, in the presence of copper powder, afforded (2-phenoxy-5-chloro)nitrobenzenes (III to VI) and [2-(4-chloro-phenylthio)-5-chloro] nitrobenzene (VII). These nitre compounds were reduced to the amino compounds (XI to XVIII) with stannous chloride and hydrochloric acid. Thiocyanation of these compounds, 2-amino-4-chlorophenol, and XIX, by treatment with ammonium thiocyanate and bromine in acetic acid afforded the thiocyano compounds (XXI to XXX). 2) Reaction of the potassium salts of p-chloro- and p-bromophenols with 2-chloro-, 4-bromo-, 2-chloro-4-fluoro-, and 2-chloro-4-iodo-nitrobenzenes, in the presence of copper powder, afforded the nitro compounds (XXXI to XXXVI), which were reduced with stannous chloride and hydrochloric acid to the amino compounds (XXXVII to XLII), and further derived to the thiocyano compounds (XLIII to XLVII) by treatment with ammonium thiocyanate and bromine. 3) All these thiocyanate compounds were submitted to antifungal tests against Candida and Trichophyton. None of the compounds showed much activity against Candida but some of the compounds had activity against Trichophyton comparable to or better than that of I.
