Synthesis and antifungal activity of some new miscellaneous s-triazoles

The reaction of aryloxyacetic acid with thiocarbohydrazide under condition of fusion gave the corresponding s-triazole derivatives 2a-c. The dicyano derivatives 3, 4 were obtained via reaction of compound 2c with [bis(methylsulfanyl)methylidine]malononitrile and/or ethoxymethylenemalotionitrile. Interaction of compound 2c with bromomalononitrile yielded the corresponding triazolothiadiazine derivative 5. In addition reaction of compound 2c with phenyl isothiocyanate furnished triazolothiadiazole derivative 6. Fusion of arylaminoacetic acids 8, 9 with thiocarbohydrazide afforded s-triazole derivatives 10, 11, respectively. The reaction of benzylthioacetic acid 12 with thiocarbohydrazide yielded the triazole derivative 13. When cyanoacetic acid 14 was reacted with thiocarbohydrazide the pyrazolotriazole derivative 16 was obtained. Some of the obtained compounds, showed remarkable antifungal activity comparable to the fungicide Mycostatine.