The present investigation was aimed at the synthesis of 2-mercaptobenzoxazole, a series of Schiff’s bases 1-[α-(arylidine hydrazino) acetyl]-2-mercaptobenzoxazole 2MB-2a-e and 2-[(aryl)-3-(acetyl amino)-1, 3-thiazolidine-4-ones]-2-mercaptobenzoxazole 2MB-3a have been synthesized from 2-mercaptobenzoxazole and compounds were screened for their antibacterial and antifungal activities by agar diffusion method. The structures of the all synthesized compounds have been determined by their IR, 1H NMR and elemental analysis. All the compounds have showed moderate to promising antibacterial and antifungal activities, against Gram-positive bacterium Bacillus subtilis (MTCC 441), Streptomyces griseus (MTCC 1540) and Gram-negative bacterium Escherichia coli (MTCC 443) and for antifungal activity against Ashbya gossypii (MTCC 358) and Aspergillus niger (MTCC 282).