An Efficient One-Pot Synthesis of 2-(Aryloxyacetyl)cyclohexane-1,3-diones as Herbicidal 4-Hydroxyphenylpyruvate Dioxygenase Inhibitors

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成果类型：

期刊论文

作者：

Wang, Da-Wei;Lin, Hong-Yan;He, Bo;Wu, Feng-Xu;Chen, Tao;...

通讯作者：

Yang, Wen-Chao;Yang, Guang-Fu

作者机构：

[Yang, Guang-Fu; Yang, Wen-Chao; Chen, Tao; Chen, Qiong; Wang, Da-Wei; Lin, Hong-Yan; Wu, Feng-Xu; He, Bo; Yang, WC; Yang, GF] Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China.

[Yang, Guang-Fu] Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 30071, Peoples R China.

通讯机构：

[Yang, WC; Yang, GF; Yang, Guang-Fu] C

Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China.

Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 30071, Peoples R China.

语种：

英文

关键词：

Acetone;Crops;Cyclohexane;Herbicides;4-Hydroxyphenylpyruvate dioxygenase;Herbicidal activity;One-pot synthesis;Structure activity relationships;Triketone;Weed control;2-(2-((1-bromonaphthalen-2-yl)oxy)acetyl)-3-hydroxycyclohex-2-en-1-one;4 hydroxyphenylpyruvate dioxygenase;acetone cyanohydrin;cyclohexanone derivative;enzyme inhibitor;ethylamine;herbicide;imidazole derivative;mesotrione;N,N-carbonyldiimidazole;naphthalene derivative;nitrile;triethylamine;antagonists and inhibitors;Arabidopsis;Brassica rapa;chemical structure;chemistry;dose response;drug effects;maize;metabolism;structure activity relation;synthesis;weed;weed control;4-Hydroxyphenylpyruvate Dioxygenase;Arabidopsis;Brassica rapa;Cyclohexanones;Dose-Response Relationship, Drug;Enzyme Inhibitors;Ethylamines;Herbicides;Imidazoles;Molecular Structure;Naphthalenes;Nitriles;Plant Weeds;Structure-Activity Relationship;Weed Control;Zea mays

期刊：

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY

ISSN：

0021-8561

年：

2016

卷：

期：

页码：

8986-8993

DOI：

10.1021/acs.jafc.6b04110

基金类别：

National Natural Science Foundation of ChinaNational Natural Science Foundation of China (NSFC) [21332004, 21372094, 21672079]

机构署名：

本校为第一且通讯机构

院系归属：

化学学院

摘要：

4-Hydroxyphenylpyruvate dioxygenase (EC 1.13.11.27, HPPD) is an important target for new bleaching herbicides discovery. As a continuous work to discover novel crop selective HPPD inhibitor, a series of 2-(aryloxyacetyl)cyclohexane-1,3-diones were rationally designed and synthesized by an efficient one-pot procedure using N,N′-carbonyldiimidazole (CDI), triethylamine, and acetone cyanohydrin in CH2Cl2. A total of 58 triketone compounds were synthesized in good to excellent yields. Some of the triketones displayed potent in vitro Arabidopsis thaliana HPPD (AtHPPD) inhibitory activity. 2-(...

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An Efficient One-Pot Synthesis of 2-(Aryloxyacetyl)cyclohexane-1,3-diones as Herbicidal 4-Hydroxyphenylpyruvate Dioxygenase Inhibitors

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