Synthesis of osthol-based botanical fungicides and their antifungal application in crop protection.

[Display omitted] • We remarkably increase the potency of osthole derivatives against the resistant phytopathogenic fungi. • We have simplified the structure of osthole and obtained the potent osthole derivatives C 4. • We indicated that the cell membrane of fungi is the key action site of C 4. Plant pathogenic fungi decrease the quality and productivity of plant production. The botanical fungicides have better biocompatibility and rapid biodegradation, little or no cross resistance, and the structural diversity, and thus are beneficial to deal with plant fungal diseases. Osthole has been widely used as the commercial botanical fungicide against powdery mildew in China. In this article, a series of osthole derivatives were synthesized, which respectively contain different substituents on the benzene ring, at the C8-position and pyrone ring. All the target compounds were evaluated in vitro for their antifungal activity against resistant phytopathogenic fungi. Colletotrichum fragariae, Strawberry Botrytis Cinerea, Kiwifruit Botrytis Cinerea, Kiwifruit brown Rots, which are common in fruit fungal diseases. The compound C 4 was identified as the most promising candidate with the EC 50 values at 38.7 µg/mL against Colletotrichum Fragariae, 14.5 µg/mL against Strawberry Botrytis Cinerea and 24.3 µg/mL against Kiwifruit Botrytis Cinerea , respectively, whereas the antifungal activity against resistant phytopathogenic fungi. of osthole is too low to be used (EC 50 > 400 ppm). The results of mycelial relative conductivity determination, PI uptake and fluorescence spectroscopy indicated that the cell membrane of fungi is the key action site of C 4. Besides, C 4 has the potent inhibitory activity against both of plant and human pathogenic bacteria. Our studies showed that C 4 was worthy for further attention as a promising botanical fungicide candidate in crop protection. [ABSTRACT FROM AUTHOR]