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Design, synthesis, insecticidal evaluation and molecular docking studies of cis-nitenpyram analogues bearing diglycine esters

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Abstract

Based on the strategies of receptor structure-guided neonicotinoid design, a series of novel cis-nitenpyram analogues bearing diglycine esters were designed and synthesized. Preliminary bioassays indicated that the insecticidal spectra of the target compounds were expanded compared with our previous work, while all the target compounds presented excellent insecticidal activities against Nilaparvata lugens and Aphis medicagini at 100 mg/L. Among these analogues, 6b showed 100% mortality against Nilaparvata lugens (LC50 = 0.163 mg/L) and 90% against Aphis medicagini at 4 mg/L. SARs suggested that the insecticidal potency of our designed cis-nitenpyram analogues was dual-controlled by the size and species of the ester groups. The molecular docking simulations revealed that the structural uniqueness of these analogues may lead to a unique molecular recognition and binding mode compared with the previously designed compounds. Introduction of the peptide bond gave rise to more significant hydrogen bonds between the nitenpyram analogues bonding with the amino acid residues of insect nAChRs. The docking results explained the SARs observed in vitro, and shed light on the novel insecticidal mechanism of these cis-nitenpyram analogues.

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Authors and Affiliations

  1. College of Life and Environment Sciences, Shanghai Normal University, Shanghai, 200234, China

    YanXia Chen, ChuanWen Sun & XiaXia Wen

  2. Jiangsu Institute of Ecomones Co., Ltd., Jintan, 213200, China

    ChuanWen Sun & WangGeng Zhang

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  1. YanXia Chen
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  2. ChuanWen Sun
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Correspondence to ChuanWen Sun.

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Chen, Y., Sun, C., Wen, X. et al. Design, synthesis, insecticidal evaluation and molecular docking studies of cis-nitenpyram analogues bearing diglycine esters. Sci. China Chem. 56, 159–168 (2013). https://doi.org/10.1007/s11426-012-4748-x

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  • DOI: https://doi.org/10.1007/s11426-012-4748-x

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