Synthesis and Herbicidal Activity of Triketone-Quinoline Hybrids as Novel 4-Hydroxyphenylpyruvate Dioxygenase Inhibitors

被引：105

作者：

Wang, Da-Wei ^{[1
]}

Lin, Hong-Yan ^{[1
]}

Cao, Run-Jie ^{[1
]}

Chen, Tao ^{[1
]}

Wu, Feng-Xu ^{[1
]}

Hao, Ge-Fei ^{[1
]}

Chen, Qiong ^{[1
]}

Yang, Wen-Chao ^{[1
]}

Yang, Guang-Fu ^{[1
,2
]}

机构：

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

[2] Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 30071, Peoples R China

来源：

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY | 2015年 / 63卷 / 23期

基金：

中国国家自然科学基金;

关键词：

4-hydroxyphenylpyruvate dioxygenase; herbicide; quinoline; triketone; rational design; P-HYDROXYPHENYLPYRUVATE DIOXYGENASE; PLANT; DERIVATIVES; ACCESS; MODE;

D O I：

10.1021/acs.jafc.5b01530

中图分类号：

S [农业科学];

学科分类号：

09 ;

摘要：

4-Hydroxyphenylpyruvate dioxygenase (EC 1.13.11.27, HPPD) is one of the most important targets for herbicide discovery. In the search for new HPPD inhibitors with novel scaffolds, triketone-quinoline hybrids were designed and subsequently optimized on the basis of the structure -activity relationship (SAR) studies. Most of the synthesized compounds displayed potent inhibition of Arabidopsis thaliana HPPD (AtHPPD), and some of them exhibited broad-spectrum and promising herbicidal activity at the rate of 150 g ai/ha by postemergence application. Most promisingly, compound III-1, 3-hydroxy-2-(2-methoxy-7-(methylthio)quinoline-3-carbonyl)cyclohex-2-enone (K-i = 0.009 mu M, AtHPPD), had broader spectrum of weed control than mesotrione. Furthermore, compound III-1 was much safer to maize at the rate of 150 g ai/ha than mesotrione, demonstrating its great potential as herbicide for weed control in maize fields. Therefore, triketone-quinoline hybrids may serve as new lead structures for novel herbicide discovery.

引用

页码：5587 / 5596

页数：10

共 35 条

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