Discovery of Arylfluorosulfates as Novel Fungicidal Agents against Plant Pathogens.

A series of arylfluorosulfates were synthesized as fungicide candidates through a highly efficient sulfur fluoride exchange (SuFEx) reaction. A total of 32 arylfluorosulfate derivatives with simple structures have been synthesized, and most of them exhibited fungal activities against five agricultural pathogens (, , , , and ). Among the target compounds, compound exhibited great antifungal activity against (EC = 1.51 μg/mL), which was comparable to commercial fungicides carbendazim and thiabendazole (EC = 0.53 and 0.70 μg/mL, respectively); compounds and exhibited antifungal activities against (EC = 1.64 and 1.73 μg/mL, respectively) comparable to carbendazim (EC = 1.02 μg/mL). The antifungal effect of compound was also evaluated on rice plants against . Significant preventive and curative efficacies were observed (89.2% and 91.8%, respectively, at 200 μg/mL), exceeding that of thiabendazole. Primary study on the mechanism of action indicated that compound could suppress the sclerotia formation of even at a very low concentration (1.00 μg/mL), destroy the cell membrane and mitochondria, trigger the release of cellular contents, produce excessive reactive oxygen species (ROS), and suppress the activity of several related enzymes. This work could bring new insights into the development of arylfluorosulfates as novel fungicides.