Design, synthesis, and insecticidal activity of novel terpenoid ester compounds containing bicyclo[2.2.1] heptane against Aphis gossypii Glover

作者：Caiyue Liu, Yuelan Yin, Hao Liu, Longfei Yang, Minghui Chen, Ting Ma, Guoqiang Zhang, Chunjuan Wang, Sifeng Zhao, Xiaoqiang Han · 发表于：Advanced Agrochem · 年份：2024 · DOI：10.1016/j.aac.2024.04.002 · 被引用次数：8 · 研究领域：Insect Pest Control Strategies、Insect and Pesticide Research、Insect-Plant Interactions and Control

To discover novel and efficient compounds against Aphis gossypii Glover, a series of novel terpene ester derivatives containing the structure of bicyclo[2.2.1]heptane were designed and synthesized using tschimganin as the lead compound. Bioactivity assays showed that most tschimganin analogs exhibited moderate to outstanding insecticidal activity against A . gossypii . In particular, compound 56 (LC 50 = 0.28 μg mL −1 ), identified as (1 S ,2 S ,4 R )-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl nicotinate, exhibited the best activity, which was significantly superior to that of imidacloprid (LC 50 = 0.54 μg mL −1 ) and sulfoxaflor (LC 50 = 0.70 μg mL −1 ). The precise and dependable 3D-QSAR model suggests a promising direction for further design of more active tschimganin-based insecticides. Metabolomics showed that compound 56 disrupted detoxification, amino acid biosynthesis, and energy metabolism and may affect the central nervous system of A. gossypii . The results of this study indicated that tschimganin analogs are a potential new class of green insecticides that can be used for the integrated management of A. gossypii . • The synthesized compound 56 showed excellent activity, and its mechanism was preliminarily investigated by metabonomics.