Synthesis of novel 9R/S-acyloxy derivatives of cinchonidine and cinchonine as insecticidal agents

Endeavor to discover biorational natural products-based insecticides, two series (27) of novel 9R/S-acyloxy derivatives of cinchonidine and cinchonine were prepared and assessed for their insecticidal activity against Mythimna separata in vivo by the leaf-dipping method at 1 mg/mL. Among all the compounds, especially derivatives 6l and 6o exhibited the best insecticidal activity with final mortality rates of 75.0% and 71.4%, respectively. Overall, a free 9-hydroxyl group is not a prerequisite for insecticidal activity and C9-substitution is well tolerated; the configuration of C8/9 position is important for insecticidal activity, and 9S-configuration is optimal; 6'-OCH3 moiety is not necessary, removal of it is also acceptable.

Automated summary

A free 9-hydroxyl group is not necessary for insecticidal activity; C9-substitution is well tolerated; the configuration of the C8/9 position is crucial for insecticidal activity, with 9S-configuration being optimal.