双杂环基甲酮类化合物的设计、合成及杀线虫活性  

Design,synthesis and nematicidal activity of bis-heterocyclic ketone compounds

作　　者：邱蝶 曹晓峰 李忠[1] 徐晓勇[1] QIU Die;CAO Xiaofeng;LI Zhong;XU Xiaoyong(Shanghai Key Laboratory of Chemical Biology,School of Pharmacy,East China University of Science and Technology,Shanghai 200237,China)

机构地区：[1]华东理工大学药学院上海市化学生物学(芳香杂环)重点实验室,上海200237

出　　处：《农药学学报》2023年第3期572-585,共14页Chinese Journal of Pesticide Science

基　　金：国家自然科学基金(21672061);国家重点研究计划项目(2018YFD0200105)。

摘　　要：植物寄生线虫可直接或间接地危害全球各类作物,造成严重的经济损失。本文设计并合成了27个未见文献报道的双杂环基甲酮类化合物,并测定了化合物在离体条件下对南方根结线虫Meloidogyne incognita的致死率及其在在沙土与基质土壤中对由南方根结线虫造成的植物根结的抑制率(活体测试)。离体测试结果表明,除化合物D1和E3在40 mg/L下72 h时对南方根结线虫的致死率分别为70.03%和71.26%外,大部分目标化合物对其无致死活性。活体测试结果表明:40 mg/L时化合物B1、B2、B5、C4、D2、E6和E9在沙土中对植物根结的抑制率均在90%以上,其中D2在5 mg/L时抑制率最高,达87.61%,且高于先导化合物B1;而在基质土壤中,化合物B5的抑制活性最强,在40 mg/L时抑制率为77.67%。初步的构效关系分析表明,不带取代基的(5-(2-噻吩基)-2-噻唑基)-2-噻吩甲酮(D2)化合物具有更好的杀线虫活性。Plant parasitic nematodes can directly or indirectly damage all kinds of crops in the world and cause serious economic losses.In this study,twenty-seven bis-heterocyclic ketones that have not been reported were designed and synthesized,and their lethal activity in vitro against Meloidogyne incognita and their inhibition rates in vivo caused by M.incognita in sand and matrix soil were measured.Results of the test in vitro showed that most of the compounds had no activity against M.incognita at 40 mg/L for 72 h,except for compounds D1 and E3,which showed 70.03%and 71.26%mortality,respectively.Results of the test in vivo showed that the inhibition rates of compounds B1,B2,B5,C4,D2,E6 and E9 in sand were higher than 90%against M.incognita at 40 mg/L,and the inhibition rate of D2 reached 87.61%at 5 mg/L,which was the highest one and higher than that of lead compound B1.In matrix soil,the inhibitory activity of compound B5 was the strongest,and the inhibition rate was 77.67%at 40 mg/L.Preliminary analysis on the structure-activity relationship demonstrated that(5-(2-thienyl)-2-thiazolyl)-2-thienylmethanone(D2)without any substituents on the 2-thiophene ring had better nematicidal activity.

关 键 词：双杂环基甲酮 南方根结线虫 杀线虫活性 结构-活性关系 

分 类 号：TQ450.1[化学工程—农药化工]