Synthesis of N-Cyclohexyl 2-{N-(3-Trifluoromethylphenyl)-[3-(trifluo-romethyl)benzoyl, 2-(substitutedphenoxy)propionyl, 2-(4,6-dime-thoxypyrimidinyl-2-oxy)benzoyl]-amino}-substituted-phenyl-acetamides via Ugi Reaction and Their HerbicidalActivity Evaluation

doi:10.6023/cjoc201507003

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (10): 2162-2167.DOI: 10.6023/cjoc201507003 Previous Articles Next Articles

Notes

利用Ugi反应合成2-{N-(3-三氟甲基苯基)-[3-(三氟甲基)苯甲酰、2-(取代苯氧)丙酰、2-(4,6-二甲氧基-嘧啶-2-氧基)苯甲酰]-氨基}-取代苯乙酰环己胺及其除草活性评价

胡汉宁^a, 黎安玲^a, 张瀚匀^b, 石德清^b

a 武汉大学中南医院武汉 430071;
b 华中师范大学农药与化学生物学教育部重点实验室武汉 430079

收稿日期:2015-07-03 修回日期:2015-07-22 发布日期:2015-08-31
通讯作者: 黎安玲 E-mail:anling888@126.com
基金资助:
国家自然科学基金(No. 21342004)和湖北省自然科学基金(No. 2015CKB741)资助项目.

Synthesis of N-Cyclohexyl 2-{N-(3-Trifluoromethylphenyl)-[3-(trifluo-romethyl)benzoyl, 2-(substitutedphenoxy)propionyl, 2-(4,6-dime-thoxypyrimidinyl-2-oxy)benzoyl]-amino}-substituted-phenyl-acetamides via Ugi Reaction and Their HerbicidalActivity Evaluation

Hu Hanning^a, Li Anling^a, Zhang Hanyun^b, Shi Deqing^b

a Zhongnan Hospital, Wuhan University, Wuhan 430071;
b Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, Central China Normal University, Wuhan 430079

Received:2015-07-03 Revised:2015-07-22 Published:2015-08-31
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21342004) and the Natural Science Foundation of Hubei Province (No. 2015CKB741).

1. Synthesis of N-Cyclohexyl 2-{N-(3-Trifluoromethylphenyl)-[3-(trifluo-romethyl)benzoyl, 2-(substitutedphenoxy)propionyl, 2-(4,6-dime-thoxypyrimidinyl-2-oxy)benzoyl]-amino}-substituted-phenyl-acetamides via Ugi Reaction and Their HerbicidalActivity Evaluation.PDF(1660KB)

Abstract

In order to find novel high active herbicidal lead compound, a series of N-cyclohexyl 2-{N-(3-trifluoromethyl-phenyl)-[3-(trifluoromethyl)benzoyl, 2-(substitutedphenoxy)propionyl, 2-(4,6-dimethoxypyrimidinyl-2-oxy)benzoyl]-amino}-substitutedphenylacetamides 3a～3i were designed and synthesized by introducing 3-trifluoromethylbenzoyl, 2-aryloxy-pro-pionyl or 2-(4,6-dimethoxypyrimidin-2-yloxy)benzoyl and 3-trifluoromethyl phenyl moieties into the molecular skeleton via the Ugi reaction. Their structures were characterized by IR, ¹H NMR, EI-MS, and elemental analyses. The preliminary bioassay (in vitro) indicated that some of compounds 3 displayed moderate to good herbicidal activity against Brassica campestris L at the concentration of 100 mg/L. The glasshouse bioassay (in vivo) showed that some of compounds 3 exhibited good herbicidal activities against B. campestris, A. retroflexus, E. crusgalli and D. sanguinalis in pre-emergence treatment at a dose of 1500 g/ha.

Key words: Ugi reaction, pyrimidinyl salicylic acid, aryloxy propanoic acid, phytoene desaturase (PDS) inhibitor, herbicidal activity

Cite this article

Hu Hanning, Li Anling, Zhang Hanyun, Shi Deqing. Synthesis of N-Cyclohexyl 2-{N-(3-Trifluoromethylphenyl)-[3-(trifluo-romethyl)benzoyl, 2-(substitutedphenoxy)propionyl, 2-(4,6-dime-thoxypyrimidinyl-2-oxy)benzoyl]-amino}-substituted-phenyl-acetamides via Ugi Reaction and Their HerbicidalActivity Evaluation[J]. Chin. J. Org. Chem., 2015, 35(10): 2162-2167.

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利用Ugi反应合成2-{N-(3-三氟甲基苯基)-[3-(三氟甲基)苯甲酰、2-(取代苯氧)丙酰、2-(4,6-二甲氧基-嘧啶-2-氧基)苯甲酰]-氨基}-取代苯乙酰环己胺及其除草活性评价

Synthesis of N-Cyclohexyl 2-{N-(3-Trifluoromethylphenyl)-[3-(trifluo-romethyl)benzoyl, 2-(substitutedphenoxy)propionyl, 2-(4,6-dime-thoxypyrimidinyl-2-oxy)benzoyl]-amino}-substituted-phenyl-acetamides via Ugi Reaction and Their HerbicidalActivity Evaluation

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