Acta Phys. -Chim. Sin. ›› 2010, Vol. 26 ›› Issue (04): 1065-1074.doi: 10.3866/PKU.WHXB20100435

• QUANTUM CHEMISTRY AND COMPUTATION CHEMISTRY • Previous Articles     Next Articles

QSAR of Macrolactone Derivatives with Herbicidal Activity

DUAN Hong-Xia, WANG Rui-Gang, ZHANG Jian-Jun, DONG Yan-Hong, LIANG Xiao-Mei, WU Jing-Ping, WANG Dao-Quan   

  1. Key Laboratory of Pesticide Chemistry and Application Technology, Ministry of Agriculture, Department of Applied Chemistry, China Agricultural University, Beijing 100193
  • Received:2009-11-27 Revised:2010-01-25 Published:2010-04-02
  • Contact: LIANG Xiao-Mei, WANG Dao-Quan E-mail:wangdq@cau.edu.cn; liangxiaomeim@yahoo.com.cn

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Abstract:

We studied the quantitative structure-activity relationships (QSAR) of macrolactone derivatives. Statistical results fromthe established comparative molecular field analysis (CoMFA), the comparative molecular similarity indices analysis (CoMSIA), and the hologram quantitative structure-activity relationship (HQSAR) models showed believable predictability based on the cross-validated value (r2cv>0.5) and the non cross-validated value (r2>0.8). A contour maps analysis of the CoMFA and CoMSIA models showed that the hydrophobic and hydrogen-bond acceptor fields are important factors that affect the herbicidal activity of macrolactone compounds except for the steric and electrostatic fields. The structural modification information from the different atom contributions in the HQSAR model is in agreement with those of the 3D-QSAR models. According to the results from the CoMFA and CoMSIA models, the structure of compound B1-3 with the best herbicidal activity was modified and some designed compounds were predicted to have higher activity.

Key words: CoMFA, CoMSIA, HQSAR, Macrolactone, Herbicidal activity