具有除草活性的吡唑啉并四嗪酮衍生物的设计、合成与定量构效关系的研究  

Design, Synthesis and Quantitative Structure-Activity Relationship Study of Herbicidal Analogues of Pyrazolotetrazinones

作　　者：朱有全[1] 成佳[1] 邹小毛[1] 胡方中[1] 肖玉虹[1] 杨华铮[1] 

机构地区：[1]南开大学元素有机化学研究所元素有机化学国家重点实验室,天津300071

出　　处：《有机化学》2008年第6期1044-1049,共6页Chinese Journal of Organic Chemistry

基　　金：国家重点基础研究发展计划(973计划)(No2003CB114400);国家自然科学基金(Nos20372040;20772066);国家高等教育博士点基金资助项目

摘　　要：设计合成了一系列未见文献报道的4-乙氧羰基-1,7-二氢-1-取代苯基-5-(未)取代吡唑啉[5,1-d][1,2,3,5]四嗪-7-酮衍生物,其结构均经过1HNMR、IR和元素分析表征.生测结果显示,与已报道的化合物相比,它们表现出较好的除草活性.定量的结构与活性关系研究表明,它们的除草活性与取代基的立体效应参数和疏水性参数呈现很好的相关性,相关系数r大于0.8.当作用对象为油菜时,化合物的活性可能主要与取代基R1的摩尔分子折射和取代基R2的疏水性参数有关.当取代基R1的摩尔分子折射参数为1.452时,相应化合物可能具有对油菜最高的除草活性;当作用对象为稗草时,化合物的活性主要与取代基R2疏水性参数和Taft(Es)参数有关.A series of 4-ethoxycarbonyl-1,7-dihydro-1-（substituted phenyl）-5-（un）substituted pyrazolo- [5,1-d] [ 1,2,3,5]tetrazin-7-one derivatives were designed and synthesized. Their structures were confirmed by ^1H NMR, IR spectra and elemental analysis. The bioassay results showed that these compounds exhibited better herbicidal activity. Quantitative structure-activity relationship studiesshowed that their herbicidal activity was correlated with the substituent molar refractivity （MR）, steric or hydrophobic physicochemical parameters, where the correlation coefficients were larger than 0.8. The herbicidal activity against Brassica campestris was mainly effected by the MR for R^1 and the hydrophobic parameter （π） for R^2. When MR was about 1.452, the compound showed the highest herbicidal activity. The herbicidal activity against E. crus-galli was mainly related with Taft （Es） for the ortho-R^2 and the hydrophobic parameter （π） for the or- tho- and meta-R^2.

关 键 词：除草活性 四嗪酮 定量构效关系 

分 类 号：S482.4[农业科学—农药学]