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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  3 b  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.

Antifungal and insecticidal activities of rhein derivatives: synthesis, characterization and preliminary structure–activity relationship studies