Preparation and Fungitoxicity of 3,6-Dichloro- and 3,6-Dibromo-8-Quinolinols

Article abstract of DOI:10.1007/BF01277632

3,6-Dichloro- and 3,6-dibromo-8-quinolinols were prepared by direct halogenation of 8-nitroquinoline by N-halosuccinimide in acetic acid or by halogenation of the corresponding 6-halo-8-nitroquinoline prepared via a Skraup reaction.The nitro group was reduced to amino and the amine was hydrolyzed to the phenol in 70percent sulfuric acid at 220 deg C.The fungitoxicity of 3,6-dichloro- and 3,6-dibromo-8-quinolinols, as well as intermediates in their preparation, against Aspergillus niger, Aspergillus oryzae, Myrothecium verrucaria, Trichoderma viride, and Mucor cirinelloides was determined. 3,6-dichloro-8-quinolinol is the most fungitoxic analogue of this class of compounds observed to date. - Keywords. 3,6-dichloro-8-nitroquinoline; 3,6-dibromo-8-nitroquinoline; 8-amino-3,6-dichloroquinoline; 8-amino-3,6-dibromoquinoline; 3,6-dichloro-8-quinolinol; 3,6-dibromo-8-quinolinol; 1H NMR spectra.