氘标记稻瘟酯的合成及其杀菌活性  

Synthesis and fungicidal activity of deuterated pefurazoate

作　　者：范鑫鑫[1] 韩敏晖 丁宇轩 张学博 李恒朝 安杰 FAN Xinxin;HAN Minhui;DING Yuxuan;ZHANG Xuebo;LI Hengzhao;AN Jie(Patent Examination Cooperation(Beijing)Center of the Patent Office,CNIPA,Beijing 100160,China;College of Science,China Agricultural University,Beijing 100193,China)

机构地区：[1]国家知识产权局专利局专利审查协作北京中心,北京100160 [2]中国农业大学理学院,北京100193

出　　处：《农药学学报》2020年第1期27-34,共8页Chinese Journal of Pesticide Science

基　　金：国家自然科学基金青年项目(21602248);国家重点研发计划(2017YFD0200504).

摘　　要：氘标记农药作为探针或者内标在农药代谢、毒理研究或者农药残留分析中发挥着重要作用。由于动力学同位素效应,C-D键比C-H键更为稳定,因此氘标记农药可能具有更长的半衰期,以及对非靶标生物更小的毒性。稻瘟酯是一种对水稻恶苗病和稻瘟病有良好防治效果的农用杀菌剂。本项研究利用单电子转移还原氘化反应和氘标记中间体,成功合成了4个不同位点被选择性氘代的稻瘟酯,其中3个化合物未见文献报道,并对其进行了杀菌活性测试。离体杀菌活性测试结果显示,上述4种氘代稻瘟酯对水稻稻瘟病菌和水稻恶苗病菌均具有良好的生物活性,与未被标记的稻瘟酯无显著差异。氘标记稻瘟酯未来可作为代谢、毒理研究的探针及农药残留分析中的内标。Deuterium labeled agrochemicals have been widely used as probes in the metabolism and toxicology study or internal standards in the agrochemical residue analysis.Because of the primary deuterium kinetic isotope effect,the cleavage of C-D bonds requires higher activation energy than that of C-H bonds.Deuterium labelled agrochemicals may have longer half-lives and reduced toxicity to non-target organism.Pefurazoate has good control effect on rice bakanae disease and rice blast.In this study,four types of deuterated pefurazoate was synthesized using novel sodium dispersions mediated single electron transfer reductive deuterations developed by Jie An’s lab,and three of them were first reported in this work.Their fungicidal activities against Pyricularia oryzae and Gibberella fujikuroi were evaluated,which were comparable to that of the unlabeled pefurazoate.The deuterated pefurazoate can be used as the probe in the metabolism study,the toxicity study or as the MS internal standard in the residue analysis.

关 键 词：氘标记农药 氘代稻瘟酯 还原氘化反应 杀菌活性 

分 类 号：TQ450.1[化学工程—农药化工] TQ455