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Paper Details

Synthesis and antifungal activity of 4-substituted aryl methyl-2-(4- acetylamino-3-bromophenyl)- 1, 3, 4-oxadiazolin-5-thiones and substituted- 1, 2, 4-triazolin-5-thiones

Rishi Pratap Singh1, Dharm Veer Singh2, C.R. Singh3*and Shailendra Singh4

Journal Title:Journal of Chemical, Biological and physical sciences

Starting material 4-acetylamino-3-bromobenzoyl hydrazine (1) has been synthesized from easily available methyl-4-acetylamino-3-bromobenzoate and hydrazine hydrate in ethanol. Compound (1) react with KOH and CS2 gives 2-(4-acetylamino-3-bromophenyl)-1, 3, 4-oxadiazoline-5-thiones (2). Aminomethylation of (2) with formaldehyde and secondary amines in ethanol furnished Manich base (3a-e). Compound (1) was again treated with arylisothiocynate to get 4-arylthiosemicarbazide (4a-d) which underwent cyclization in the presence of NaOH to give corresponding triazolinthione (5a-d). Compound (5a-d) on aminomethylation with formaldehyde and secondary amine in ethanol to give aryl1-1, 2, 4-triazoline-5-thiones (6a-l). Antfungal activity has been compaired with Dithane M-45, a commercial fungicide, for their fungitoxic action against Phytophthora infestance and Collectotricum falcatum, and the result correlated with their structural features.