A series of new [1,2,4]triazolo[3,4-b][1,3,4]thiadiazines incorporating α and β-naphthoxy methyl moieties was synthesized starting from S-substituted 5-[(naphthalen-1/2-yloxy)methyl]-1,3,4-oxadiazole-2-thiols. The newly synthesized compounds were characterized by 1H NMR, IR, mass and elemental analysis. The efficacy of the compounds was tried with regard to their antimicrobial and antioxidant properties.