In the present study, the interaction of 4-(N-substituted)-3-pyridyl-5-mercapto-s-triazole with secondary amines was explored. The Isonicotinic acid hydrazide was converted into the corresponding potassium dithiocarbazinate, by reacting with carbon disulphide in alkaline medium which undergoes ring closure reaction after further treatment with aqueous potassium hydroxide to give 5-pyridyl-2-mercapto-1,3,4-oxadiazole. 4-(N-pyridylcarboxamido)-3- pyridyl- 5-mercapto-s-triazole and 3-pyridyl-4-amino-5-mercapto-s-triazole were obtained in one pot reaction by heating equimolar quantities of oxadiazole with isonicotinic acid hydrazide and hydrazine hydrate respectively. Condensation of triazole with secondary amines in anhydrous dimethyl sulfoxide results in the formation of corresponding quaternary salts. The synthesized compounds were confirmed by IR, 1HNMR spectra and elemental analysis. All the compounds were screened for their preliminary in-vitro antibacterial and antifungal activity.