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Synthesis, evaluation of insecticidal activity, and crystal analysis of cis-nitenpyram analogs bearing 1,4-dihydropyridine

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Abstract

A new series of nitenpyram analogs were designed by introducing 1,4-dihydropyridine to fix the pharmacophore (–C=C–NO2) into the cis-configuration, as confirmed by X-ray diffraction. Crystal structure analysis showed that there was a homoconjugation effect on these cis-nitenpyram analogs, and a huge conjugated system comprising the 1,4-dihydropyridine scaffold and the ester group at the 3 position. Preliminary bioassays showed that most of the target compounds exhibit good insecticidal activities (>80 %) at 100 mg/dm3 against Aphis medicagini, while a 4-fluorophenyl cis-nitenpyram analog afforded the best activity, with >90 % mortality at 20 mg/dm3. These excellent insecticidal activities imply that this huge conjugated system results in an enhanced π–π interaction between the molecule and amino acid residues in receptors. Further studies on the mode of action of one of these cis-nitenpyram analogs and structural modifications are in progress.

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Acknowledgments

The insecticidal activity test of the target compounds was completed by the Bioassay Department, Branch of National Pesticide R&D South Center, Hangzhou. We are grateful for the support from Branch of National Pesticide R&D South Center. This work was supported by the National Natural Science Foundation of China (21042010, 21102092, and 30870560), the Key Scientific “Twelfth Five-Year” National Technology Support Program (2011BAE06B01-17), the Innovation Project of Shanghai Education Commission (12YZ078), the Leading Academic Discipline Project of Shanghai Normal University (DZL808), and Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University (07dz22303).

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Authors and Affiliations

  1. College of Life and Environment Sciences, Shanghai Normal University, No. 100 Guilin Road, Xuhui district, Shanghai, 200234, China

    Chuanwen Sun, Tianyan Liu, Li Ding & Yanxia Chen

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

    Wanggeng Zhang

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  1. Chuanwen Sun
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  2. Tianyan Liu
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  3. Li Ding
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  4. Yanxia Chen
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  5. Wanggeng Zhang
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Correspondence to Chuanwen Sun.

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Sun, C., Liu, T., Ding, L. et al. Synthesis, evaluation of insecticidal activity, and crystal analysis of cis-nitenpyram analogs bearing 1,4-dihydropyridine. Monatsh Chem 144, 1003–1012 (2013). https://doi.org/10.1007/s00706-012-0872-8

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  • DOI: https://doi.org/10.1007/s00706-012-0872-8

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