N-[4氯-2-取代-5(3-甲基-2,6-二氧-4-三氟甲基-2,3-二氢嘧啶-1(6H)-基)苯基]-N-取代苯氧乙(丙)酰胺类化合物的合成及除草活性  

Synthesis and Herbicidal Activity of Novel N-(2,4-Dichloro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-2,3-dihydropyrimidin-1(6H)-yl)phenyl)-2-phenoxypropanamide

作　　者：李丹[1] 孙炯[2] 任叶果[2] 黄明智[2] 

机构地区：[1]长沙理工大学化学与生物工程学院,长沙410114 [2]湖南化工研究院国家农药创制工程技术研究中心,长沙410007

出　　处：《农药》2011年第4期253-257,共5页Agrochemicals

基　　金：国家自然科学基金资助项目(20872033);湖南省教育厅资助科研项目(05C232)

摘　　要：[方法]脲嘧啶类化合物和苯氧羧酸类化合物均具有较高的生物活性。为了寻找高效、低毒的除草活性化合物,以2,4-二氯苯胺和3-氨基-4,4,4-三氟甲基丁烯酸乙酯为原料,经关环、氮甲基化、硝化、还原得到中间体3-(5-胺基-2,4-二氯苯基)-6-(三氟甲基)-1-甲基嘧啶-2,4(1H,3H)-二酮,其与芳氧乙(丙)酰氯反应,合成了16个未见文献报道的N-[4氯-2-取代-5(3-甲基-2,6-二氧-4-三氟甲基-2,3-二氢嘧啶-1(6H)-基)苯基]-N-取代苯氧乙(丙)酰胺类化合物(3),所有目标化合物结构均通过1H NMR、IR、LC/MS确认。[结果]在75 g a.i./hm2剂量下芽后茎叶处理,化合物3d、3f、3i化合物对刺苋、藜双子叶杂草的抑制率达90%以上,表现出较好的抑制活性;化合物3d、3f对苘麻的抑制率分别达80%、90%,但是大部分化合物无活性。[结论]将具有不同除草机理除草活性的脲嘧啶结构与苯氧羧酸结构有机的结合起来,从生物活性来看,初步设计的化合物不是很成功,该类化合物的结构优化正在进行中。[Methods] Uracil derivatives and the phenoxy carboxylic acid have great biological activities.in search of high herbicidal compounds with low toxin,sixteen novel N-（2,4-dichloro-5-（3-methyl-2,6-dioxo-4-（trifluoromethyl）-2,3-dihydropyrimidin-1（6h）-yl）phenyl）-2-phenoxypropanamide（3） were designed and synthesized utilizing 4-fluoro-aniline and ethyl 3-amino-4,4,4-trifluorobut-2-enoate as raw materials.The chemical structures of all compounds were confirmed by 1h Nmr,ir,and lc/ms.subsequently,the herbicidal activities of the as-prepared compounds were evaluated in the greenhouse.[Results] At the dosage of 75 g a.i./ha,compounds 3d,3f,3i possessed above 90% herbicidal control at post-emergence treatments against dicotyledonous weeds,such as Amaranthus spinosus,chenopodium album l.,3d,3f showed 80 and 90% herbicidal control against Abutilon theophrasti medic.most of compounds had no herbicidal activities.[Conclusions] combined with uracil derivatives and the phenoxycarboxyl acid which have different mode of action.From the herbicidal activities of compounds,primarily designed compounds were not successful,and the optimization of this kind of compounds was still in process.

关 键 词：脲嘧啶 苯氧羧酸 合成 除草活性 

分 类 号：TQ457.2[化学工程—农药化工]