Citation: Yang Zihui, Chen Aiyu, Hu Aixi, Ye Jiao. Synthesis, Crystal Structure and Herbicidal Activity of N-(Thiazol-2-yl)-2-(4-aryloxyphenoxy) propionamides[J]. Chinese Journal of Organic Chemistry, ;2017, 37(1): 149-156. doi: 10.6023/cjoc201607041 shu

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

Yang Zihui ,
Chen Aiyu ,
Hu Aixi ^*,, ,
Ye Jiao ^*,,

Colleage of Chemistry and Chemical Engineering, Hunan University, Changsha 410082

Corresponding author: Hu Aixi, axhu@hnu.edu.cn Ye Jiao, yejiao@hnu.edu.cn
Received Date: 27 July 2016
Revised Date: 26 August 2016

Fund Project: the National Science and Technology Pillar Program of China During the Twelfth Five-year Plan Period 2011BAE06B01

Figures(4)

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, D_c=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.
- 2-(4-aryloxyphenoxy) propionamide,
- thiazole,
- synthesis,
- herbicidal activity
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