Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (1): 149-156.DOI: 10.6023/cjoc201607041 Previous Articles     Next Articles



杨子辉, 陈爱羽, 胡艾, 希叶姣   

  1. 湖南大学化学化工学院 长沙 410082
  • 收稿日期:2016-07-27 修回日期:2016-08-26 发布日期:2016-09-08
  • 通讯作者: 胡艾希, 叶姣;
  • 基金资助:

    十二五国家科技支撑计划(No. 2011 BAE06B01)资助项目.

Synthesis, Crystal Structure and Herbicidal Activity of N-(Thiazol-2-yl)-2-(4-aryloxyphenoxy) propionamides

Yang Zihui, Chen Aiyu, Hu Aixi, Ye Jiao   

  1. Colleage of Chemistry and Chemical Engineering, Hunan University, Changsha 410082
  • Received:2016-07-27 Revised:2016-08-26 Published:2016-09-08
  • Supported by:

    Project supported by the National Science and Technology Pillar Program of China During the Twelfth Five-year Plan Period(No. 2011BAE06B01).

Eighteen N-(thiazol-2-yl)-2-(4-aryloxyphenoxy) propionamides were synthesized by reaction of(R)-(+)-2-(4-hy-droxyphenoxy) propanoyl chlorides with 2-aminothiazole derivatives.Their structures were confirmed by 1H NMR,13C NMR,elemental analysis,EI-MS and optical rotation.The crystal structure of(R)-N-(4-trifluoromethyl-5-ethoxycarbonylthiazole-2-yl)-2-[4-(3-fluoro-5-chloropyridin-2-yl) oxy) phenoxy) propionamide was determined by X-ray diffraction analysis.The crystal belonged to the tetragonal system,space group P41212 with a=14.45502(18)Å,b=14.45502(18)Å,c=21.7813(5)Å;Z=8,V=4551.14(15)Å3,Dc=1.558 Mg/m3,F(000)=2176,μ=3.013 mm-1,and the final R=0.0302,wR=0.0687.The bioassay results indicated that most of title compounds displayed moderate to excellent herbicidal activity against crabgrass(Digitaria sanguinalis) and barnyard grass(Echinochloa crusgalli) at the dose of 1500 g/hm2.Some compounds showed 100% inhibition against the growth of the crabgrass and barnyard grass when applied at the pre-emergence and post-emergence treatment.

Key words: 2-(4-aryloxyphenoxy) propionamide, thiazole, synthesis, herbicidal activity