N-取代吡啶基-2-酰基四氢哒嗪-1(2H)-硫代甲酰胺的合成及除草活性  

Synthesis and Herbicidal Activities of N-Substituted Pyridyl-2-acyltetrahydropyridazine-1(2H)-carbothioamides

作　　者：张浩[1] 刘瑞全[1] 李奇博 李青阳[1] 陈亚红 刘克昌[1] 刘尚钟[1] 

机构地区：[1]中国农业大学理学院应用化学系,北京100193 [2]北京颖泰嘉和生物科技有限公司,北京100192

出　　处：《有机化学》2015年第7期1506-1513,共8页Chinese Journal of Organic Chemistry

基　　金："十二五"科技支撑计划(No.2011BAE06B03);国家自然科学基金(No.21172256)资助项目~~

摘　　要：以取代氨基吡啶为原料，经二步反应合成关键中间体——取代吡啶基异硫氰酸酯，再分别与4个制各的取代六氢哒嗪中间体缩合，合成了4个系列共22个新型Ⅳ_取代吡啶基-2-酰基四氢哒嗪-1（2H）-硫代甲酰胺类化合物8～11．所有目标产物的结构均经过1HNMR，13CNMR和HRMS的确证．初步的除草活性测试表明，部分化合物在375护ha叫剂量下，对双子叶杂草苘麻及反枝苋和单子叶杂草马唐具有约100％芽前抑制活性．进一步活性筛选发现，2-[（5-氯吡啶-2-基）硫代氨基甲酰基]四氢哒嗪-1（2／4）-甲酸乙酯（9e）在45g·ha-1剂量下对苘麻的抑制率仍达到95％．Key intermediates--substituted pyridyl isothiocyanates, which were prepared from starting material substituted pyridyl amines via two steps, were further condensed with four substituted hexahydropyridazine intermediates to afford four series of novel N-substituted pyridyl-2-acyltetrahydropyridazine-1（2H）-carbothioamides 8-11. The structures of all compounds have been confirmed by 1H NMR, 13C NMR and HRMS techniques. The preliminary bioassay results indicated that some of the title compounds exhibited approximately 100% inhibition against Abutilon theophrasti, Amaranthus retroflexus and Digitaria sanguinalis at a dose of 375 g.ha-1. In particular, ethyl 2-（（5-chloropyridin-2-yl）carbamothioyl）tetrahydropyridazine-1（2H）-carboxylate （9e） displayed the best pre-emergence herbicidal effect against Abutilon theophrasti with 95% inhibitory activity even at 45 g.ha-1.

关 键 词：酰氨基硫脲 六氢哒嗪 吡啶 合成 除草活性 

分 类 号：TQ450.1[化学工程—农药化工]