College of Agriculture, Yangtze University, Jinzhou, China.
Department of Chemistry, College of Science, China Agricultural University, Beijing, P. R. China.
Nat Prod Res. 2021 Dec;35(24):5773-5777. doi: 10.1080/14786419.2020.1836631. Epub 2020 Oct 20.
The introduction of fluorine atom can increase the biological activities of the target compounds remarkably. To find more safe and efficient insecticides, natural product galegine as lead compound, a series of novel fluorinated galegine analogues were designed and synthesized. The bioassay results indicate that all the target compounds have moderate to high insecticidal activities against Geoffroy and Glover, in particular, compounds IIa-05, IId-02 and IIe-03 show the best insecticidal activities against with the mortality of 100%, 100% and 96.6%, respectively. And compounds IIa-02, IId-02, IId-04, IIc-01, IIc-02 and IId-01 show 0.6-7 times insecticidal activities against as Imidacloprid with their LC values are 0.28 mg/L, 0.38 mg/L, 0.33 mg/L, 0.09 mg/L, 0.03 mg/L and 0.12 mg/L, respectively The analysis of structure-activity relationship indicates that the compounds with difluoro-substituted benzene ring have more potent insecticidal activities than the single fluoro-substituted compounds.
引入氟原子可以显著提高目标化合物的生物活性。为了寻找更安全、更有效的杀虫剂，我们以天然产物藜芦定作为先导化合物，设计并合成了一系列新型氟化藜芦定类似物。生物测定结果表明，所有目标化合物对 Geoffroy 和 Glover 均具有中等至高的杀虫活性，特别是化合物 IIa-05、IId-02 和 IIe-03 对 表现出最佳的杀虫活性，死亡率分别为 100%、100%和 96.6%。化合物 IIa-02、IId-02、IId-04、IIc-01、IIc-02 和 IId-01 对 表现出 0.6-7 倍的杀虫活性，其 LC 值分别为 0.28 mg/L、0.38 mg/L、0.33 mg/L、0.09 mg/L、0.03 mg/L 和 0.12 mg/L，与吡虫啉相当。构效关系分析表明，具有二氟取代苯环的化合物比单氟取代化合物具有更强的杀虫活性。
