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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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Chemical Research in Chinese Universities 2015年第2期31卷 228-234页

作者： ZHANG Lizhi REN Zhengjiao LU Aimin ZHAO Zheng XU Wenqin BAO Qianqian DING Weijie YANG Chunlong Jiangsu Key Laboratory of Pesticide Science Key Laboratory of Monitoring and Management of Crop Diseases and Pest lnsects Ministry of Agriculture College of Science Nanjing Agricultural University Nanjing 210095 P R. China

Twenty-seven novel pyrrolidine-2,4-dione derivatives containing N-substituted phenylhydrazine moiety were synthesized. Their structures were confirmed by IH NMR, 13C NMR and MS. The half effective concentration （ECs0） values of the title compounds against the phytopathogenic fungi Rhizoctonia cerealis were evaluated. Com- pounds 61 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 q2 value of 0.585 and Noncross-validated correlation coefficient r2 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.

关键词： pyrrolidine-2,4-dione N-Substituted phenylhydrazine Antifungal activity 3D quantitative structure activity relationship(3 D-QSAR)

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Synthesis and bioactivity of novel 3-(1-hydroxyethylidene)-5-substituted-pyrrolidine-2,4-dione derivatives

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Chinese Chemical Letters 2012年第9期23卷 1023-1026页

作者： B ao Feng Han Qing Ming Shi Xian Feng Wang Jian Bo Liu Sheng Qiang Chun Long Yang Key Laboratory of Monitoring and Management of Crop Diseases and Pest Insects Ministry of AgricultureNanjing Agricultural UniversityChina Nanjing 210095 Jiangsu Key Laboratory of Pesticide Science Nanjing Agricultural UniversityChina Nanfing 210095 College of Life Science Nanjing Agricultural UniversityChina Nanjing 210095

Ten novel 5-substituted derivatives of 3-（1-hydroxyethylidene）pyrrolidine-2,4-dione were synthesized. The compounds were confirmed by IR, 1H NMR, MS and elemental analysis. The bioassay indicated that these compounds showed noticeable herbicidal activities, and compounds 6f and 6j exhibited excellent inhibitory activities against the stalk of Echinochloa crusgalli, with ECso values of 94.4 and 72.7 rag/L, respectively.

关键词： Tenuazonic acid pyrrolidine-2,4-dione Synthesis Herbicidal activity

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