In this paper, 15 new compounds of 2-N-2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl-4-(N-substituted-phenyl)- imino-5-methyl-1,2,4-triazoles (2a～2e), 4-(N-substituted-phenyl)imino-5-methyl-1,2,4-triazole-3-thiones (3a～3e) and 2-N-2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl-4-(N-substituted-phenyl)imino-5-methyl-1,2,4-triazoles (4a～4e) were rationally designed and synthesized according to the principle of superposition of bioactive substructures by the combination of 1,2,4-triazole, Schiff base and glucosides. Firstly, the Schiff base 4-arylideneamino-1,2,4-triazole-3-thiones (1a～1e) has been obtained by the reaction of 4-amino-1,2,4-triazole-3-thiones with substituted salicyladehyde in weak acidic conditions. Then the target compounds 2a～2e were prepared from 4-arylideneamino-1,2,4-triazole-3-thiones with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide in the presence of potassium hydroxide. The structures of target compounds have been characterized by ¹H NMR, ¹³C NMR, IR and elemental analysis. The results of preliminary bioassay showed that most of the tested compounds displayed variable inhibitory activity. Especially, compounds 4b exhibited much higher activities against Escherichia coli and Staphylococcus aureus than commercial fungicide fluconazole with minimum inhibitory concentration (MIC) values of 16 μg/mL. All of the compounds showed excellent activity against fungal strains with MIC values of 16 μg/mL, which were more effective against Monilia albican than the reference drug triclosan.