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Chinese Journal of Organic Chemistry >

2025 , Vol. 45 >Issue 1: 196 - 204

DOI: https://doi.org/10.6023/cjoc202407021

ARTICLES

Design, Synthesis and Bioactivity of Novel 2-Phenylethanol Ester Derivatives Containing Monoterpene Fragments

  • Shixiang Pan ,
  • Yan Liu ,
  • Zhuo Shi ,
  • Xingxing Lu ,
  • Yaoguo Qin ,
  • Cheng Qu ,
  • Chen Chen ,
  • Xinling Yang
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  • a Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193
    b Department of Entomology, College of Plant Protection, China Agricultural University, Beijing 100193)
    c Institute of Plant Protection, Beijing Academy of Agriculture and Forestry Sciences, Beijing 100097
†These authors contributed equally to this work.
*E-mail:

Received date: 2024-07-09

  Revised date: 2024-08-16

  Online published: 2024-09-30

Supported by

National Natural Science Foundation of China(22277136)

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Abstract

To discover novel aphid control agents, taking plant volatile 2-phenylethanol as a lead, 16 ester derivatives of 2-phenylethanol containing monoterpenoid fragments were designed and synthesized by the method of active substructure splicing. The binding affinity of target compounds to odorant binding proteins (OBP) of Acyrthosiphon pisum and Harmonia axyridis was measured via fluorescent competitive binding assay. All compounds showed good binding affinity to both proteins, better than 2-phenylethanol. Behavioral experiments showed that all target compounds had repelling activity against A. pisum (35.9%~57.7%) with 3-methoxyphenethyl (E)-3,7-dimethylocta-2,6-dienoate (3f) exhibiting the best repellency. In addition, 3f also showed significant attractive activity to H. axyridis. The binding mode of 3f with the OBP protein was investigated by molecular docking, revealing that the introduction of the monoterpenoid fragment significantly enhanced the hydrophobic interactions between compounds and proteins. Preliminary toxicity tests indicated that 3f was safe to H. axyridis, showing great application prospects in the green control of aphids.

Key words： 2-phenylethanol; odorant binding protein; repel aphid; attract ladybug; eco-friendliness

Cite this article

Shixiang Pan , Yan Liu , Zhuo Shi , Xingxing Lu , Yaoguo Qin , Cheng Qu , Chen Chen , Xinling Yang . Design, Synthesis and Bioactivity of Novel 2-Phenylethanol Ester Derivatives Containing Monoterpene Fragments[J]. Chinese Journal of Organic Chemistry, 2025 , 45(1) : 196 -204 . DOI: 10.6023/cjoc202407021

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