高等学校化学学报 ›› 2016, Vol. 37 ›› Issue (8): 1442.doi: 10.7503/cjcu20160335

• 有机化学 • 上一篇    下一篇

基于呋喃酚构建2-(4-芳氧苯氧基)丙酰胺及除草活性

杨子辉, 李贝贝, 叶姣, 胡艾希()   

  1. 湖南大学化学化工学院, 长沙410082
  • 收稿日期:2016-05-12 出版日期:2016-07-19 发布日期:2016-07-19
  • 作者简介:

    联系人简介: 胡艾希, 男, 博士, 教授, 博士生导师, 主要从事药物化学研究. E-mail: axhu@hnu.edu.cn

  • 基金资助:
    “十二五”国家科技支撑计划项目(批准号: 2011BAE06B01)资助

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

YANG Zihui, LI Beibei, YE Jiao, HU Aixi*()   

  1. College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China
  • Received:2016-05-12 Online:2016-07-19 Published:2016-07-19
  • Contact: HU Aixi E-mail:axhu@hnu.edu.cn

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.

关键词: 2-(4-芳氧苯氧基)丙酰胺, 呋喃酚, 除草活性

Abstract:

2-(4-Aryloxyphenoxy) propionamide derivatives were identified as one of the most important herbicides, which inhibited acetyl-CoA carboxylase(ACCase) to restrict fatty acid. Recent years, 2-(4-aryloxyphenoxy) propionamide derivative have developed resistance in varying degrees among weeds. Therefore, resear-ching novel 2-(4-aryloxyphenoxy) propionamide derivatives herbicide is of great importance. Seventeen of 2-(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 by 1H NMR, 13C 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.

Key words: 2-(4-Aryloxyphenoxy) propionamide, Benzofuranol, Herbicidal activity(Ed.: P, H, Y, K)

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