Synthesis and Herbicidal Activity of Triketone-Quinoline Hybrids as Novel 4-Hydroxyphenylpyruvate Dioxygenase Inhibitors
Synthesis and Herbicidal Activity of Triketone-Quinoline Hybrids as Novel 4-Hydroxyphenylpyruvate Dioxygenase Inhibitors
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新型 4-羟基苯基丙酮酸双加氧酶抑制剂三酮-喹啉杂化物的合成及其除草活性
DOI：
10.1021/acs.jafc.5b01530
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发表时间：
2015-06-17
影响因子：
6.1
通讯作者：
Yang, Guang-Fu
中科院分区：
文献类型：
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作者：
Wang, Da-Wei;Lin, Hong-Yan;Yang, Guang-Fu
4-羟苯丙酮酸双加氧酶（Hydroxyphenylpyruvate 1.13.11.27，HPPD）是除草剂研究的重要靶标之一。在寻找具有新型骨架的新HPPD抑制剂的过程中，设计了三酮-喹啉杂合物，并随后基于结构-活性关系（SAR）研究进行了优化。大多数合成的化合物显示出对拟南芥HPPD（AtHPPD）的有效抑制作用，其中一些化合物在芽后施用量为150 g ai/ha时表现出广谱和有希望的除草活性。最有希望的是，化合物III-1，3-羟基-2-（2-甲氧基-7-（甲硫基）喹啉-3-羰基）环己-2-烯酮（Ki = 0.009 μ M，AtHPPD）比甲基磺草酮具有更广谱的杂草控制。此外，化合物III-I在150 g ai/ha的比率下比甲基磺草酮对玉米安全得多，证明了其作为除草剂用于玉米田杂草控制的巨大潜力。因此，三酮-喹啉杂化物可作为新型除草剂发现的新先导结构。
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.