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Synthesis, biological activity and 3D-QSAR study of novel pyrrolidine-2,4-dione derivatives containing N-substituted phenylhydrazine moiety

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Abstract

Twenty-seven novel pyrrolidine-2,4-dione derivatives containing N-substituted phenylhydrazine moiety were synthesized. Their structures were confirmed by 1H NMR, 13C NMR and MS. The half effective concentration (EC50) values of the title compounds against the phytopathogenic fungi Rhizoctonia cerealis were evaluated. Compounds 6l and 6q displayed good bioactivity with EC50 values of 1.626 and 2.043 μg/mL, respectively. The 3D quantitative structure activity relationship(3D-QSAR) model of CoMFA was established with reliable cross-validated correlation coefficient q 2 value of 0.585 and Noncross-validated correlation coefficient r 2 value of 0.971. This model provided a tool for guiding further design and synthesis of novel pyrrolidine-2,4-dione derivatives with high fungicidal activity.

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Authors and Affiliations

  1. Jiangsu Key Laboratory of Pesticide Science, Nanjing Agricultural University, Nanjing, 210095, P. R. China

    Lizhi Zhang, Zhengjiao Ren, Wenqin Xu & Chunlong Yang

  2. Key Laboratory of Monitoring and Management of Crop Diseases and Pest Insects, Ministry of Agriculture, Nanjing Agricultural University, Nanjing, 210095, P. R. China

    Aimin Lu, Zheng Zhao & Chunlong Yang

  3. College of Science, Nanjing Agricultural University, Nanjing, 210095, P. R. China

    Lizhi Zhang, Zhengjiao Ren, Aimin Lu, Zheng Zhao, Wenqin Xu, Qianqian Bao, Weijie Ding & Chunlong Yang

Authors
  1. Lizhi Zhang
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  2. Zhengjiao Ren
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  3. Aimin Lu
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  4. Zheng Zhao
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  5. Wenqin Xu
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  6. Qianqian Bao
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  7. Weijie Ding
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  8. Chunlong Yang
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Corresponding author

Correspondence to Chunlong Yang.

Additional information

Supported by the National High Technology Research and Development Program of China(No.2011AA10A206), the National Key Technologies R&D Program of China(No.2011BAE06B04), the Science & Technology Pillar Program of Jiangsu Province, China(No.BE2012371), the National Natural Science Foundation of China(No.31171889) and the Fundamental Research Funds for the Central Universities of China(No.KYZ201223).

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Zhang, L., Ren, Z., Lu, A. et al. Synthesis, biological activity and 3D-QSAR study of novel pyrrolidine-2,4-dione derivatives containing N-substituted phenylhydrazine moiety. Chem. Res. Chin. Univ. 31, 228–234 (2015). https://doi.org/10.1007/s40242-015-4348-3

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  • DOI: https://doi.org/10.1007/s40242-015-4348-3

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