Synthesis, anti-oomycete and fungal activities of resveratrol sulfonate derivatives containing three esters moieties

Abstract

In order to explore novel natural product-based anti-oomycete and fungal agents, thirteen unreported resveratrol sulfonate derivatives containing three esters moieties were designed and prepared using the principle of activity superposition, and structurally confirmed by 1H NMR, 13C NMR, HRMS, and m.p. Furthermore, we evaluated the target compounds (3a–m) as anti-oomycete and fungal activities against two serious agricultural diseases of Phytophthora capsici and Fusarium graminearum, respectively. Among the thirteen resveratrol sulfonate derivatives tested, three compounds 3d, 3k, and 3l exhibited the most potent anti-oomycete activity against P. capsici with EC50 values of 27.31, 27.69, and 26.14 mg/L, respectively. Moreover, two compounds 3e and 3l exhibited the most potent anti-fungal activity against F. graminearum with EC50 values of 75.81, and 73.60 mg/L, respectively. Overall, the anti-oomycete activity against P. capsici of the target compound was significantly better than that of the anti-fungal activity against F. graminearum. In particular, anti-oomycete and fungal activities showed that the structural skeleton presentation activity was closely related to the different substituents of the sulfonyloxy groups, especially the anti-oomycete activity. This study will lay a solid foundation for further modifying resveratrol to develop potential new fungicides.