高等学校化学学报 ›› 2010, Vol. 31 ›› Issue (12): 2419.

• 研究论文 • 上一篇    下一篇

N-硝基脲类化合物除草活性的3D-QSAR研究

申晓霞,徐胜臻,陈长水   

  1. 华中农业大学理学院化学系, 武汉  430070
  • 收稿日期:2010-01-06 修回日期:2010-05-05 出版日期:2010-12-10 发布日期:2010-12-06
  • 通讯作者: 陈长水 E-mail:chenchang@mail.hzau.edu.cn
  • 作者简介:陈长水, 男, 教授, 主要从事农药化学和有机化学领域的研究.
  • 基金资助:

    国家自然科学基金(批准号: 39770845)和华中农业大学学科交叉基金(批准号: 52204\|08101)资助.

3D-QSAR Study of N-Nitro Urea Derivatives with Herbicidal Activity

SHEN Xiao-Xia, XU Sheng-Zhen, CHEN Chang-Shui   

  1. Department of Chemistry,   College of Science, Huazhong Agricultural University, Wuhan 430070, China
  • Received:2010-01-06 Revised:2010-05-05 Online:2010-12-10 Published:2010-12-06
  • Contact: CHEN Chang-Shui E-mail:chenchang@mail.hzau.edu.cn
  • About author:陈长水, 男, 教授, 主要从事农药化学和有机化学领域的研究.
  • Supported by:

    National Natural Science Foundation-funded projects

摘要: 经活性测试,N-硝基脲类化合物对反枝苋(A. retroflexus L)和苏丹草(S. sudanenses)呈现除草活性。为进一步设计高活性的目标化合物,采用比较分子力场(CoMFA)对38个N-硝基脲类化合物进行三维定量构效关系(3D-QSAR)分析,建立了相关性显著、预测能力强的3D-QSAR模型(反枝苋:q2=0.674, r2=1.000, R2pred=0.9989,苏丹草:q2=0.635, r2=1.000, R2pred=0.9958)。根据CoMFA模型的立体场和静电场三维等势线图,在N’-苯环2, 5位引入体积大的正电荷取代基;3位引入负电荷基团;4, 6位引入体积大的负电荷基团有利于提高目标化合物对双子叶杂草反枝苋的除草活性,而在2位引入体积大的负电荷基团;3位引入体积小的负电荷基团;4位引入体积大的正电荷基团;5位引入体积大的取代基有利于提高目标化合物对单子叶杂草苏丹草的除草活性。

关键词: N-硝基脲, 除草活性, 定量构效关系分析(3D-QSAR), 比较分子力场(CoMFA)

Abstract: The preliminary bioassays indicated that N-nitro urea derivatives possess good activity against A. retroflexus L and S. sudanenses. To design the highly active title compounds, comparative molecular field analysis (CoMFA) was applied to study of the three-dimensional quantitative structure activity relationship (3D-QSAR) on 38 N-nitro urea derivatives. The reasonable models with predictive ability were obtained from the investigation (A. retroflexus L: q2=0.674, r2=1.000, R2pred=0.9989) and (S. sudanenses: q2=0.635, r2=1.000, R2pred=0.9958). The steric and electronic contour maps show that bulky and electropositive groups inked to 2, 5-position of N'-phenyl ring, electronegetive groups to 3-position, small and electronegetive groups to 4, 6-position may increase the herbicidal activity against A. retroflexus L, and also bulky and electronegetive groups to 2-position, small and electronegetive groups to 3-position, bulky and electropositive groups to 4-position, bulky groups to 5-position may increase the activity against S. sudanenses.

Key words: N-nitro urea, herbicidal activity, 3D-QSAR, CoMFA

TrendMD: