Abstract

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 Hyalopterus pruni Geoffroy and Aphis gossypii Glover, in particular, compounds IIa-05, IId-02 and IIe-03 show the best insecticidal activities against Hyalopterus pruni 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 Aphis gossypii as Imidacloprid with their LC₅₀ 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.

摘要

氟原子的引入可以显着提高目标化合物的生物活性。为寻找更安全高效的杀虫剂，以天然产物galegine为先导化合物，设计合成了一系列新型氟化galegine类似物。生物测定结果表明，所有目标化合物均具有中至高度的杀虫活性，对紫花苜蓿Geoffroy和Aphis gossypii Glover，尤其是化合物IIa-05、IId-02和IIe-03的杀虫活性最好，死亡率较低。分别为 100%、100% 和 96.6%。并且化合物IIa-02、IId-02、IId-04、IIc-01、IIc-02和IId-01对棉蚜表现出0.6-7倍的杀虫活性如吡虫啉，其LC ₅₀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 构效关系分析表明化合物具有二氟取代苯环的杀虫活性比单一的氟取代化合物具有更强的杀虫活性。