橙酮衍生物的合成、晶体结构及除草活性  

Synthesis,Crystal Structure and Herbicidal Activity of Aurone Derivatives

作　　者：刘斌[1] 张敏[1] 谢龙观[1] 李永红[1] 徐效华[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：《高等学校化学学报》2011年第10期2335-2340,共6页Chemical Journal of Chinese Universities

基　　金：国家自然科学基金(批准号:20872070)资助

摘　　要：设计合成了17个橙酮类化合物,X射线单晶衍射分析显示其双键为Z型.测定了它们对稗草地上部分和油菜根长的抑制率.结果表明,部分化合物对双子叶植物油菜有较好的活性,表现出良好的选择性.当浓度为100μg/mL时,化合物15对油菜胚根的抑制率达到88.5%,接近商品除草剂甲基磺草酮的活性,当浓度为10μg/mL时其对油菜胚根的抑制率达到81.3%.初步构效关系研究表明,橙酮A环上的电子效应以及分子的亲水与疏水性对保持其活性有重要的作用,为进一步结构优化提供了依据.Pesticides based on natural products have attracted more and more attentions.They are low-toxic,readily degradable and low drug-resistant.This is an important field for developing new pesticides.Previous effords were mainly focused on developing new insecticides and bactericides.So there are few commercial herbicides originated from natural products.Aurones are natual product existing in fruits and flowers of certain plants.It was found that some of them show certain herbicidal activity.Herein,seventeen aurones derivatives were synthesized.X-ray single crystal diffraction analysis showed that the conformation of its double bond was Z.And these compounds were assayed for their inhibiting activity against Echinochloa crusgalli and B rassica cam pestris.The results indicate that they displayed modest inhabitation toward B rassica cam pestris,but bad toward Echinochloa crusgalli.Under 100 μg/mL,inhibiting rate of compoud 15 on B rassica cam pestris was up to 88.5%,and it reached to 81.3% given by subsequent rescreening at 10 μg/mL.Electronic property on ring A and lgP value of the whole molecular play a important role in maintainning its activiy.Compound 15 is a good leading structure for further optimization.

关 键 词：橙酮衍生物 除草活性 晶体结构 

分 类 号：O621.3[理学—有机化学]