Various 5-β-[(N-Benzenesulphonyl/tosyl)-4-(un) substituted anilino] ethyl-2-H/CH3/C6H5/-CH2C6H5/p-NO2C6H4-1,3,4-oxadiazoles (5a-d), 5--β-[(N-Benzenesulphonyl/tosyl)-4-(un)-substituted anilino] ethyl-2-(N,N-diethylamino/anilino/morpholino)-1, 3, 4-oxadiazoles (6a-r), 3--β-[(N-Benzenesulphonyl/tosyl)-4-(un) substituted anilino] ethyl-4-amino-5-mercapto-4(H)-1, 2, 4-triazoles (7a-f) and 5--β-[(N-Benzenesulphonyl/tosyl)-4-(un)substituted anilino] ethyl-3-(p-toluidino) methyl-1, 3, 4-oxadiazole-2-thiones (8a-f) with sulphonamide moiety at the side chain were synthesised. The structures of the newly synthesised compounds were established on the basis of their spectral data and elemental analysis. All the compounds were screened for antimicrobial activities against Escherichia coli, Bacillus cirroflagellosus, Aspergillus niger, Colletotrichum capsici. Most of the compounds have exhibited significant antifungal activity against Colletotrichum capsici, moderate activity against Aspergillus niger and minimum antibacterial activity against both the strains.