新型含氟1,2,4-三唑[3,4-b]-1,3,4-噻二唑衍生物的合成及其除草活性  

Synthesis and Herbicidal Activities of Novel Fluorine-Containing 1,2,4-Triazolo[3,4-b]-1,3,4-thiadiazole Derivatives

作　　者：吴小盛 汤君[1] 陈朴青[2] 王涛[1] 罗劲[1,2] WU Xiao-sheng TANG Jun CHEN Pu-qing WANG Tao LUO Jin(a. Jiangxi Province Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineerin b. Analytical ＆ Testing Center, 1. Jiangxi Normal University, Nanehang 330022, China)

机构地区：[1]江西师范大学化学化工学院江西省化学生物学重点实验室,江西南昌330022 [2]江西师范大学分析测试中心,江西南昌330022

出　　处：《合成化学》2017年第6期475-479,486,共6页Chinese Journal of Synthetic Chemistry

基　　金：国家自然科学基金资助项目(21262018;21562026);江西省自然科学基金资助项目(20161BAB203085);江西省自然科学青年基金资助项目(20161BAB213072)

摘　　要：以对氟苯甲酰肼为初始原料,经成盐、环化和一锅法反应制得中间体5-对氟苯基-2,4-二氢-1,2,4-三唑-3-硫酮磷亚胺(4);4与芳基异氰酸酯发生氮杂Wittig反应,后经成环反应合成了11个新型的含氟6-芳氨基-1,2,4-三唑[3,4-b]-1,3,4-噻二唑衍生物(6a^6k),其结构经~1H NMR,^(13)C NMR,IR和HR-MS表征。对单、双子叶植物的除草活性测试结果表明:浓度为100 mg·L^(-1)时,6c和6f对稗草和萝卜的茎和根的生长表现出优异的抑制活性,抑制率高达100%。5 - （4-Fluorophenyl） -2,4-2H- 1,2,4-triazolo [ 3,4-b ] -1,3,4-thiadiazole iminophosphorane （4） was prepared by salt forming, eyclization and one pot reaction, using benzoyl hydraziono as start- ing material. Eleven novel fluorine-containing 1,2,4-triazolo [ 3,4-b ] -1,3,4-thiadiazole derivatives （6a -6k） were successfully synthesized by the aza-Wittig reaction with 4 with arylisocyanates, and then annulation reaction. The structures were characterized by 1H NMR, 13C NMR, IR and HR-MS. The results of preliminary bioassay demonstrated that 6c and 6f showed 100% inhibitory activities on barnyard grass and radish at the dosage of 100 mg · L-1.

关 键 词：氮杂WITTIG反应 1 2 4-三唑[3 4-b]-1 3 4-噻二唑 合成 除草活性 

分 类 号：O626.2[理学—有机化学]