含咪唑啉酮结构的吡唑类对羟基苯基丙酮酸双加氧酶抑制剂的除草活性及选择性研究

徐玉玲; 林红艳; 吴丰旭; 康德来; 杨文超; 杨光富

doi:10.16801/j.issn.1008-7303.2017.0055

含咪唑啉酮结构的吡唑类对羟基苯基丙酮酸双加氧酶抑制剂的除草活性及选择性研究

doi: 10.16801/j.issn.1008-7303.2017.0055

1.
武汉轻工大学化学与环境工程学院, 武汉 430023
2.
华中师范大学化学学院农药与化学生物学教育部重点实验室, 武汉 430079

基金项目:

国家公益性行业（农业）科研专项（21372093，201203022）;国家自然科学基金（21372093，21672079）

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出版历程
- 收稿日期: 2017-04-23
- 刊出日期: 2017-08-09

Herbicidal activity and selectivity profiles of imidazole ketone-containing p-hydroxyphenylpyruvate dehydrogenase inhibitors

1.
School of Chemical & Environmental Engineering, Wuhan Polytechnic University, Wuhan 430023, China
2.
Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, China

摘要

摘要: 对羟基苯基丙酮酸双加氧酶（HPPD）是一种重要的除草剂作用靶标。为了发现具有高活性和高选择性的新型HPPD抑制型除草剂，对前期合成的23个含咪唑啉酮结构单元的吡唑类衍生物（2A~2W）进行了深入的生物活性评价和构效关系研究，比较了它们对拟南芥HPPD（AtHPPD）和人源HPPD（hHPPD）抑制活性的差异，从酶水平上总结了该类化合物的结构-活性关系和种属选择性规律，从活体植株水平研究了它们的除草活性。结果表明：部分化合物表现出良好的除草活性和作物安全性，其中化合物2E和2G在150 g/hm2剂量下对荠菜、繁缕、小藜和棒头草抑制活性达到80%以上，且其对作物的安全性也明显优于商品化除草剂硝磺草酮。此外，化合物2P在酶水平上的选择性倍数高达93倍，展示出良好的应用潜力。
- 咪唑啉酮 /
- 对羟基苯基丙酮酸双加氧酶 /
- 除草剂 /
- 除草活性 /
- 作物安全性
Abstract: p-Hydroxyphenylpyruvate dehydrogenase (HPPD) is an important target in herbicide discovery. In order to discover new HPPD inhibitor-based herbicide with high activity and selectivity, the comprehensive bioevaluation of our previously synthesized imidazole ktone-containing HPPD inhibitors was conducted and the structure-activity relationship was studied. More specifically, the in vitro inhibitory activities against Arabidopsis thaliana HPPD (AtHPPD) and human HPPD (hHPPD) were studied and the selectivity profile was evaluated. Their herbicidal activities in plants were then evaluated. Some compounds showed high HPPD enzyme inhibition activities and herbicidal activities. Especially, the compounds 2E and 2G exhibited good control effect toward broadleaf weeds in winter field at the dose of 150 g/hm2. More importantly, their crop safety profiles is superior to the commercial herbicide mesotrione. In addition, compound 2P exhibited excellent selectivity (about 93 times) that is about 23-fold higher than that of mesotrione, which showing a good application potential.
- imidazole ketone /
- p-hydroxyphenylpyruvate dehydrogenase /
- herbicide /
- herbicidal activity /
- crop safety

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