Discovery of Novel Potential Aphid Repellents: Geranic Acid Esters Containing Substituted Aromatic Rings
文献类型： 外文期刊
作者： Pan, Shixiang 1 ; Li, Wenhao 1 ; Qin, Yaoguo 2 ; Yang, Zhaokai 1 ; Liu, Yan 1 ; Shi, Zhuo 1 ; Qu, Cheng 3 ; Luo, Chen 3 ; Yang, Xinling 1 ;
作者机构： 1.China Agr Univ, Coll Sci, Innovat Ctr Pesticide Res, Dept Appl Chem, Beijing 100193, Peoples R China
2.China Agr Univ, Coll Plant Protect, Dept Entomol, MOA Key Lab Monitoring & Environm Friendly Contro, Beijing 100193, Peoples R China
3.Beijing Acad Agr & Forestry Sci, Inst Plant Protect, Beijing 100097, Peoples R China
关键词： molecular design; ester; aphids; repel; odorant-binding proteins; molecular docking
期刊名称：MOLECULES （ 影响因子：4.927； 五年影响因子：5.11 ）
ISSN：
年卷期： 2022 年 27 卷 18 期
页码：
收录情况： SCI
摘要： Aphids are one of the most damaging agricultural pests. For the sake of novel eco-friendly compounds with good activity for aphid control, a series of novel geranic acid esters containing substituted aromatic rings were designed by inverting ester groups of lead compounds. All compounds were characterized by HRMS, H-1-NMR, and C-13-NMR. In order to identify the effect of inversion ester groups on activity, a bioassay was conducted. The results showed that the repellent activity against Acyrthosiphon pisum (A. pisum) and the binding affinity with the odorant-binding protein 9 from A. pisum (ApisOBP9) of the compounds were increased after inversion of the ester groups. Particularly, 5f showed the best repellent activity (repellency proportion: 55.6%) and binding affinity (1/Ki: 0.49 mu M). Meanwhile, the structure-activity relationships revealed that the introduction of meta-substitution of the benzene ring and halogen atoms, such as Cl and Br, facilitated the biological activity. The further molecular docking results demonstrated that hydrogen bonding interactions and hydrophobic interactions were vital for the binding affinity with ApisOBP9. Additionally, all compounds were predicted to be eco-friendly and their volatile physicochemical properties have been enhanced compared to the leads. The present results provide valuable clues for the further rational design of aphids' behavioral control agents.
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