Two series of new 2-[4-((1H-benzimidazol-2-ylthio)methyl)-1H-1,2,3-triazol-1-yl]N`-(arylmethylidene) acetohydrazides (4-14) and 2-[4-((1H-benzimidazol-2-ylthio)methyl)-1H-1,2,3-triazol-1-yl]N`-(α-arylethylidene) acetohydrazides (15-20) were prepared by the reaction of 2-[4-((1H-benzimidazol-2-ylthio)methyl)-1H-1,2,3-triazol-1- yl]acetohydrazide (3) and the appropriate (un) substituted benzaldehyde or acetophenones. The purity of all new compounds was checked by TLC and elucidation of their structures was confirmed by IR, 1H NMR, and mass spectrometry along with elemental microanalyses. All the target compounds were evaluated for their possible antimicrobial activity. Most of the tested compounds showed moderate to good antibacterial activity against most of the bacterial strains used in comparison with ciprofloxacin as a reference drug. The most active compounds were (7), (13), (15), and (20). Results of antifungal activity revealed that all compounds showed a good and potent antifungal activity in comparison to fluconazole as a reference drug. Compounds (8), (9), (13) and (14) were the most active compounds