N-硝基脲类化合物除草活性的3D-QSAR研究  

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

作　　者：申晓霞[1] 徐胜臻[1] 陈长水[1] 

机构地区：[1]华中农业大学理学院化学系,武汉430070

出　　处：《高等学校化学学报》2010年第12期2419-2424,共6页Chemical Journal of Chinese Universities

基　　金：国家自然科学基金(批准号:39770845);华中农业大学学科交叉基金(批准号:52204-08101)资助

摘　　要：经活性测试发现,N-硝基脲类化合物对反枝苋(A.retroflexusL)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可知,在N'-苯环的2和5位引入大体积的正电荷取代基,3位引入负电荷基团,4和6位引入大体积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位引入大体积的负电荷基团,3位引入小体积的负电荷基团,4位引入大体积的正电荷基团,5位引入大体积的取代基均有利于提高目标化合物对单子叶杂草苏丹草的除草活性.Urea derivatives have occupied a pivotal position in pesticide chemistry due to their significant activities,including herbicidal activities,antimicrobial and so on.And N-nitro substituted anilines also displayed herbicidal properties.So we proposed that urea derivatives bearing a new group nitro in the NH—CO—NH bridge should display some interesting fungicidal activities.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 the 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;S.sudanenses：q2=0.635,r2=1.000,R2pred=0.9958）.The steric and electronic contour maps show that bulky and electropositive groups linked 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.

关 键 词：N-硝基脲 除草活性 三维定量构效关系 比较分子力场 

分 类 号：O621.13[理学—有机化学] O641[理学—化学]