Design, Synthesis And Bioactivity Of Thiazole And Pyrrole Derivatives Incorporated With Natural Amino-acids And Carbohydrates

Thiazole and pyrrole derivatives have attracted much attention, due to their bioactivity as acaricides, bactericides and herbicides. Carbohydrate and amino acid derivatives represent classes of natural compounds possessing a broad spectrum of biological activity. It was designed that by utilizing those familiar natural orgainc molecule as building blocks to look for potential new hits or leads. After structurally incorporated with the sugar or amino acid molecules, the lead candidates with favourable bioactivity could be anticipated. The reason is that those new molecules could be metabolized more easily by natural microorganism enzymes.In order to discover potential biorational pesticides, five series of new compounds were designed and synthesized by utilizing carbohydrate and amino acid, including 2,3-dihydro-2-phenylsulfonylhydrazono-3-glycosylthiazoles,2,3-dihydro-2-phenylsulfonyl-hydrazono-3-phenylthiazoles, N-phenyl-N’-amino thioureas and its ring closed derivatives and 3-phenylpyrrolidin-2-one.1H/13C HMBC measurements corroborated by X-ray crystallographic results revealed the exclusive regioselectivity of these ring closures of 2,3-dihydrothiazoles toward the N-4 position of the thiosemicarbazide moiety.Preliminary bioassay showed that all the tested compounds display some fungicidal activities.3-Phenylpyrrolidin-2-one possess rational herbicidal activity, 2,3-dihydro-2-phenylsulfonylhydrazono-3-phenylthiazoles and 3-phenylpyrrolidin-2-one possess rational acaricidal activity.The structures of one hundred and one novel products were characterized by 1H NMR, MS and elemental analysis, partial compounds were characterized by 13C NMR.