基于呋喃酚构建2-(4-芳氧苯氧基)丙酰胺及除草活性  

Synthesis and Herbicidal Activity of 2-( 4-Arylxoyphenoxy) propionamide Derivatived from Benzofuranol

作　　者：杨子辉[1] 李贝贝[1] 叶姣[1] 胡艾希[1] 

机构地区：[1]湖南大学化学化工学院,长沙410082

出　　处：《高等学校化学学报》2016年第8期1442-1450,共9页Chemical Journal of Chinese Universities

基　　金："十二五"国家科技支撑计划项目(批准号:2011BAE06B01)资助~~

摘　　要：以呋喃酚为原料,采用2条合成路线制备2种关键中间体2-氨基-1-(2,2-二甲基-7-烷氧基-2,3-二氢苯并呋喃-5-基)乙酮盐酸盐(2)和n-(2,2-二甲基-2,3-苯并呋喃-7-氧基)烷胺(9),再经2-(4-芳氧苯氧基)丙酰化合成了17种基于呋喃酚的2-(4-芳氧苯氧基)丙酰胺,其化学结构经核磁共振谱、高分辨率质谱和旋光度确证.除草活性测试结果表明,在1500 g/hm2剂量下,大部分化合物对单子叶杂草马唐(Crabgrass)和稗草(Barnyard grass)均具有较高的抑制活性.在化合物4和5中,有7个化合物对单子叶杂草表现为A级除草活性,如化合物4a,4b,4i,5a,5c,5e和5h对马唐和稗草的抑制率为100%.初筛结果显示,在375 g/hm2剂量下,化合物4a,4b,4i,5e和5h对稗草的茎叶处理抑制率达96%以上.2-（ 4-Aryloxyphenoxy） propionamide derivatives were identified as one of the most important herbicides,which inhibited acetyl-Co A carboxylase（ ACCase） to restrict fatty acid. Recent years,2-（ 4-aryloxyphenoxy） propionamide derivative have developed resistance in varying degrees among weeds. Therefore,researching novel 2-（ 4-aryloxyphenoxy） propionamide derivatives herbicide is of great importance. Seventeen of2-（ 4-aryloxyphenoxy） propionamide derivatives were synthesized by multistep synthetic procedures with two key intermediates 2 and 9,starting from（ R）-（ ＋） 2-（ 4-hydroxyphenoxy） propanoic acid and benzofuranol.The intermediate 9 was synthesized from o-phthalic anhydride and 2-aminoethanol via substitution reaction,bromination,etherification and amination. The synthetic reaction condition of intermediates 9 was discussed.The structures of target compounds 4 and 5 were confirmed by1 H NMR,13 C NMR,HRMS and optical rotation. The bioassay results indicated that most of title compounds possessed a moderate herbicidal activity against crabgrass and barnyard grass at 1500 g/hm2. The compounds 4a,4b,4i,5e and 5h showed more than 96% activities against the crabgrass and barnyard grass at 375 g/hm2.

关 键 词：2-(4-芳氧苯氧基)丙酰胺 呋喃酚 除草活性 

分 类 号：O626[理学—有机化学]