Semi-Preparation and X-ray Single-Crystal Structures of Sophocarpine-Based Isoxazoline Derivatives and Their Pesticidal Effects and Toxicology Study.

Recently, research and development of novel pesticides from natural plant products have received much attention. To accelerate the application of sophocarpine as the agrochemical candidate, a series of novel sophocarpine-based isoxazoline derivatives were prepared by the 1,3-dipolar [2 + 3] cycloaddition reaction of sophocarpine with different chloroximes. Their structures were well characterized by high-resolution mass spectra, infrared spectra, and proton/carbon-13 nuclear magnetic resonance spectra. Eight steric configurations of compounds , , , , , , , and were further determined by X-ray single-crystallography. Against Van der Goot, compounds (LD: 0.032 μg/nymph) and (LD: 0.024 μg/nymph) exhibited greater than 3.7- and 4.9-fold potent aphicidal activity compared to sophocarpine (LD: 0.118 μg/nymph). Against Boisduval, derivative displayed the most promising acaricidal activity with the LC value of 0.247 mg/mL, which was 14.2-fold that of sophocarpine. Compounds and also exhibited good control efficacy against . Scanning electron microscopy images indicated that compound can destroy the mite cuticle layer. These results will provide the foundation for the structural modification and use of sophocarpine derivatives as agrochemicals in the future.