A series of novel 2-((1H-imidazol-1-yl)methyl)-5-fluoro-6-(substituted/unsubstituted)-1H-benzo[d]imidazoles were prepared by condensation of the dihydrochloride salts of the appropriate 1,2-phenylene diamines with 1-(cyano methyl) imidazole and screened for antitubercular activity against H37RV strain and antifungal activity against Candida species. To examine the influence of imidazole and phenyl ether moiety on the activity chlorine substituted fluoro benzimidazole (8a) was synthesized. The newly synthesized compounds were characterized by I.R, 1H-NMR, 13C-NMR, Mass and elemental analysis. The most active derivatives of the present series were the imidazole substituted fluoro benzimidazole and the para chloro phenyl ether analog indicating the importance of a halogenated phenyl ether nucleus and the azole moiety at the 6th position. The results suggest that these two molecules are potential candidates for further development as antitubercular and antifungal agents.