Synthesis of new fungicidal imidazo- and benzimidazo[2,1-b]-1,3-thiazinones involving ring transformation of 5-oxazolone derivatives
1992
Yadav, L.D.S. | Vaish, A.
Michael-type addition of 2-imidazolidinethione (Ia) and 2-mercaptobenzimidazole (Ib) to 4-benzylidene-5-oxazolones IIa-e followed by ring transformation of the resulting Michael adducts IIIa-j yielded new compounds, 6-acet(and benz)amido-7-aryl-2,3,6,7-tetrahydro-5H-imidazo [2,1-b]-l,3-thiazin-5-ones IVa-e and 3-acet(and benz)amido-2-aryl-2,3-dihydro-4H-benzimidazo[2,1-b]-1,3-thiazin-4-ones IVa-j, respectively, in one pot. The compounds IIIa, IIIf, IIIi, and IVa-j were compared with Dithane M-45, a commercial fungicide, for their antifungal activity against Aspergillus niger and Fusarium oxysporium, and the results were correlated with the structural features of the tested compounds.
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