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

doi:10.6023/cjoc201607041

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

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N-(噻唑-2-基)-2-[4-(芳氧基)苯氧基]丙酰胺的合成、晶体结构与除草活性

杨子辉, 陈爱羽, 胡艾, 希叶姣

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 E-mail:axhu@hnu.edu.cn;yejiao@hnu.edu.cn
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

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,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.

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

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Yang Zihui, Chen Aiyu, Hu Aixi, Ye Jiao. Synthesis, Crystal Structure and Herbicidal Activity of N-(Thiazol-2-yl)-2-(4-aryloxyphenoxy) propionamides[J]. Chin. J. Org. Chem., 2017, 37(1): 149-156.

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N-(噻唑-2-基)-2-[4-(芳氧基)苯氧基]丙酰胺的合成、晶体结构与除草活性

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

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