The synthesis of 6-(tert-butyl)-8-fluoro-2,3-dimethylquinoline carbonate derivatives and their antifungal activity against Pyricularia oryzae

Abstract

A series of novel 6-(tert-butyl)-8-fluoro-2,3-dimethylquinoline carbonate derivatives were designed and synthesized. Bioassay results showed that some of them exhibited good activity against Pyricularia oryzae (P. oryzae). It was found that the compound 5q (benzyl (6-(tert-butyl)-8-fluoro-2,3-dimethylquinolin-4-yl) carbonate) possessed good activity against P. oryzae whatever protective activity (10 mg·L⁻¹) or curative activity (25 mg·L⁻¹), which was better than that of control tebufloquin. In addition, the frontier molecular orbit results revealed that the compound held higher activity against P. oryzae when the total energy was low and the ClogP was high, which may provide useful information for further design novel fungicides.

Graphical abstract

Keywords

quinoline / synthesis / antifungal activity / rice blast / SAR

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