There is an urgent need to replace highly polluting pesticides with environmentally friendly green pesticides of high efficiency and low toxicity, because of the growing concern for quality and safety of agricultural products. To discover new pesticides with diverse chemical structures from natural products, a series of rhein derivatives 3a-9b were designed, synthesized, and evaluated for their antifungal activity and insecticidal activity. The bioassay showed that some compounds exhibited moderate antifungal activity against Rhizoctonia solani, but lower activity against the other five pathogens. Surprisingly, most compounds displayed potent insecticidal activity against Spodoptera litura and Tetranychus cinnabarinus at a concentration of 2 μmol/mL. In particular, compounds 3a, 5a and 3b exhibited potent insecticidal activities against S. litura at 72 h, with mortality rates of 100%, 100% and 92.1%, respectively, which were equivalent to that of the insecticide fipronil (100%).Their structure-activity relationships were also discussed. The findings of this experiment provide helpful research ideas for the development of these rhein derivatives as novel natural product-based pesticides in crop protection.
In the search for crop protectants, amino acid ester conjugates have been widely investigated as potential antifungal agents. In this study, a series of rhein–amino acid ester conjugates were designed and synthesized in good yields, and their structures were confirmed by 1H-NMR, 13C-NMR and HRMS. The bioassay results revealed that most of the conjugates exhibited potent inhibitory activity against R. solani and S. sclerotiorum. In particular, conjugate 3c had the highest antifungal activity against R. solani with an EC50 value of 0.125 mM. For S. sclerotiorum, conjugate 3m showed the highest antifungal activity with an EC50 value of 0.114 mM. Satisfactorily, conjugate 3c exhibited better protective effects than that of the positive control, physcion, against powdery mildew in wheat. This research supports the role of rhein–amino acid ester conjugates as potential antifungal agents for plant fungal diseases.
BACKGROUNDPlant pathogenic fungal infections have become a severe threat to the yield and quality of agricultural products, and new green antifungal agents with high efficiency and low toxicity are needed. In this study, a series of thiasporine A derivatives containing phenylthiazole‐1,3,4‐oxadiazole thione (ketone) structures were designed and synthesized, and their antifungal activities against six invasive and highly destructive phytopathogenic fungi were evaluated.RESULTSThe results found that all compounds showed moderate to potent antifungal activity against six phytopathogenic fungi, and most of the E series compounds showed remarkable antifungal activity against Sclerotinia sclerotiorum and Colletotrichum camelliaet. In particular, compounds E1–E5, E7, E8, E13, E14, E17, and E22 showed more significant antifungal activity against S. sclerotiorum, with half‐maximal effective concentration (EC50) values of 0.22, 0.48, 0.56, 0.65, 0.51, 0.39, 0.60, 0.56, 0.60, 0.63, and 0.45 μg mL−1, respectively, which were superior to that of carbendazim (0.70 μg mL−1). Further activity studies showed that compound E1 possessed superior curative activities against S. sclerotiorum in vivo and better inhibitory effects on sclerotia germination and the formation of S. sclerotiorum compared with those of carbendazim.CONCLUSIONSThis study indicates that these thiasporine A derivatives containing phenylthiazole‐1,3,4‐oxadiazole thione structures might be used as antifungal agents against S. sclerotiorum. © 2023 Society of Chemical Industry.
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