Synthesis and Antifungal Activity of Pyrimidine Derivatives Containing an Amide Moiety

Abstract

In this study, 17 novel pyrimidine derivatives containing an amide moiety were synthesized. Then their <i>in vitro</i> antifungal activities against <i>Botryosphaeria dothidea</i> (<i>B. dothidea</i>), <i>Phomopsis</i> sp., and <i>Botrytis cinereal</i> (<i>B. cinereal</i>) were determined. A preliminary biological test showed that compounds 5-bromo-2-fluoro<i>-N</i>-(2-((2-methyl-6-(trifluoromethyl)pyrimidin-4-yl)oxy)phenyl)benzamide (<b>5f</b>) and 5-bromo-2-fluoro-<i>N</i>-(3-((2-methyl-6-(trifluoromethyl)pyrimidin-4-yl)oxy)phenyl)benzamide (<b>5o</b>) exhibited higher antifungal activity against <i>Phomopsis</i> sp., with an inhibition rate of 100% compared to that of Pyrimethanil at 85.1%. In particular, compound <b>5o</b> exhibited excellent antifungal activity against <i>Phompsis</i> sp., with the EC₅₀ value of 10.5 μg/ml, which was even better than that of Pyrimethanil (32.1 μg/ml). As far as we know, this is the first report on the antifungal activities against <i>B. dothidea</i>, <i>Phomopsis</i> sp., and <i>B. cinereal</i> of this series of pyrimidine derivatives containing an amide moiety.