Synthesis and Pesticidal Activities of Ester Derivatives of the Labdane Diterpenoid Andrographolide at the C-3 Position Containing the Isoxazoline Fragment and Their Toxicology Study against Tetranychus cinnabarinus Boisduval

Due to the long-term overuse of chemical pesticides, serious resistance and negative problems on human health and the ecological environment have appeared. To develop plant-product-based pesticide candidates, a series of novel andrographolide ester derivatives containing the isoxazoline skeleton were prepared at the C-3 position. Their pesticidal activities were evaluated against three typical pests such as Mythimna separata Walker, Aphis citricola Van der Goot, and Tetranychus cinnabarinus Boisduval. Against M. separata, compounds Ik, IIf, IIg, and IIk showed 1.6–1.8 times insecticidal activity compared to that of andrographolide; against A. citricola, compounds 6, Ih, and IIh possessed 3.7–3.9-fold aphicidal activity compared to that of andrographolide; against T. cinnabarinus, compounds Ib, Ig, and IIk exhibited 7.4–9.1-fold promising acaricidal activity compared to that of andrographolide. It is worth mentioning that effects of IIk on morphological changes of the treated mite cuticle layer structures were observed by the scanning electron microscope imaging method. Compound IIk can be studied as a pesticidal lead for further structural modification.