2-取代氨基-5-去氢枞基-1,3,4-噁二唑衍生物的合成及除草活性  

Synthesis and Herbicidal Activity of 2-Substituted Amino-5-dehydroabietyl-1,3,4-oxadiazole Derivatives

作　　者：莫启进[1] 段文贵[1] 李行任[1] 黄丹平[1] 罗湛江[1] 

机构地区：[1]广西大学化学化工学院,南宁530004

出　　处：《有机化学》2011年第7期1114-1121,共8页Chinese Journal of Organic Chemistry

基　　金：广西林产化学品开发与应用重点实验室开放基金(No.GXFC08-04);广西自然科学基金重点(No.2010GXNSFD013013)资助项目

摘　　要：以去氢枞酸为原料,经酰化后与水合肼反应合成去氢枞酰肼3,再与芳基异硫氰酸酯反应,得到中间体1-去氢枞酰基-4-取代基氨基硫脲4,4在Hg(OAc)2/EtOH条件下关环,合成得到一系列新型2-取代氨基-5-去氢枞基-1,3,4-噁二唑化合物5.采用IR,MS,1H NMR,13C NMR和元素分析等方法对中间体4和目标产物5进行了分析和表征.初步的除草活性测试表明,化合物4和5对油菜的胚根生长以及对稗草的幼苗生长有一定的抑制作用,其中化合物4d在浓度为100 mg/L时对油菜胚根生长的抑制率达88.2%.Dehydroabietic acid chloride was prepared by the reaction of dehydroabietic acid with thionyl chloride, followed by the reaction of the dehydroabietic acid chloride with hydrazine hydrate to provide dehydroabietacyl hydrazine. A series of target compounds 2-substituted amino-5-dehydroabietyl-1,3,4-oxadiazoles 5 were synthesized by the cyclization of 1-dehydroabietacyl-4-substituted thiosemicarbazides （4） under catalysis of Hg（OAc）2/EtOH. And the intermediates 4 were prepared by the reaction of dehydroabietacyl hydrazine with aryl isothiocyanates. The intermediates 4 and target compounds 5 were analyzed and characterized by means of IR, MS, 1H NMR, 13C NMR techniques and elemental analysis. The preliminary herbicidal assay showed that all the compounds 4 and 5 exhibited a certain growth inhibition on rape root （Brassica campestris） and barnyard grass （Echinochloa crusgalli （L.））. Among the tested compounds, 4d displayed 88.2% inhibition on rape root （Brassica campestris） at 100 mg/L concentration in herbicidal tests.

关 键 词：去氢枞酸 1-去氢枞酰基-4-取代基氨基硫脲 2-取代氨基-5-去氢枞基-1 3 4-噁二唑 除草活性 

分 类 号：TQ252[化学工程—有机化工] TQ457