The aim of this work was to find out the efficiency of N1–[(2-substituted-benzylidene-imino- 5'- methylene)-1',3',4'-thiadiazole]-2-methylbenzimidazoles, 4(a-n) and N1–[2'-( 4-substituted phenyl-3- chloro-azetidin-2-one-5'-methylene)-1',3',4'-thiadiazole]-2-methylbenzimidazole, 5(a-n) for the synthesis by conventional and greenar approach in terms of yield and reaction time along with antimicrobial activity against Bacillus subtilis, Escherichia coli, Klebsiella pneumoniae and Streptococcus aureus bacteria and Aspergillus niger, Aspergillus flavus, Fusarium oxisporium and Trichoderma viride fungi in vitro at 50 and 100 ppm concentrations. Some of the compounds displayed pronounced biological activity. The structures of all the new compounds were established on the basis of micro analytical and spectral (IR, 1HNMR and mass) data.