Synthesis, aphicidal activity and conformation of novel insect kinin analogues as potential eco‐friendly insecticides

Zhang, Chuanliang; Li, Xinlu; Song, Dunlun; Ling, Yun; Zhou, Yuanlin; Yang, Xinling

doi:10.1002/ps.5721

Title: Synthesis, aphicidal activity and conformation of novel insect kinin analogues as potential eco‐friendly insecticides

Journal Article · 06 January 2020 · Pest Management Science

DOI: https://doi.org/10.1002/ps.5721 · OSTI ID:1581203

Zhang, Chuanliang ^[1]; Li, Xinlu ^[1]; Song, Dunlun ^[2]; Ling, Yun ^[1]; Zhou, Yuanlin ^[1];

^[1]

Department of Applied Chemistry College of Science, China Agricultural University Beijing P. R. China
Department of Entomology College of Plant Protection, China Agricultural University Beijing P. R. China

Abstract BACKGROUND The discovery of ecofriendly insecticides through a new strategy for aphid control is important because of the substantial resistance and unexpected eco‐toxicity to honeybees caused by traditional insecticides. The insect kinins, a class of multifunctional insect neuropeptides, are considered for potential application in pest control. In our previous work we developed several series of insect kinin analogues and found a promising lead II‐1 with good aphicidal activity. To seek further eco‐friendly aphicides, the optimization of II‐1 is carried out in this study. RESULTS Fifteen novel Yaa ³ modified analogues based on the lead II‐1 were synthesized. The aphicidal tests indicated that IV‐3 , IV‐5 and IV‐10 exhibited significant activity against the soybean aphid Aphis glycines with LC ₅₀ values of 0.0029, 0.0072 and 0.0086 mmol L ^–1 , respectively, higher than that of lead II‐1 and the commercial Pymetrozine. The molecular modeling results showed that analogues II‐1 , IV‐3 , IV‐5 , IV‐7 and IV‐10 formed a β‐turn‐like conformation, while the conformation of analogues IV‐1 , IV‐2 and IV‐9 seemed to be linear. Some structural elements favorable for the activity were proposed based on the conformation‐activity relationship of the analogues. CONCLUSION Insect kinin analogues derived from lead II‐1 by modifying the hydrolysis site Yaa ³ with natural, sterically hindered α‐ and β‐amino acids showed great potential as eco‐friendly insecticides. Inspiringly, the most active analogue IV‐3 can be a candidate for further development. The β‐turn‐like conformation and the orientation of the aromatic rings of the side chain of Phe ² and Trp ⁴ may be critical factors beneficial to activity. © 2019 Society of Chemical Industry

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Sponsoring Organization:: USDOE

OSTI ID:: 1581203

Journal Information:: Pest Management Science, Journal Name: Pest Management Science Vol. 76 Journal Issue: 10; ISSN 1526-498X

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: United Kingdom

Language:: English

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Cited by: 6 works

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