An Efficient One-Pot Synthesis of 2-(Aryloxyacetyl)cyclohexane-1,3-diones as Herbicidal 4-Hydroxyphenylpyruvate Dioxygenase Inhibitors.
An Efficient One-Pot Synthesis of 2-(Aryloxyacetyl)cyclohexane-1,3-diones as Herbicidal 4-Hydroxyphenylpyruvate Dioxygenase Inhibitors.
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DOI：
10.1021/acs.jafc.6b04110
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发表时间：
2016-11
影响因子：
6.1
通讯作者：
Da-Wei Wang;Hong-Yan Lin;Bo He;Feng-Xu Wu;Tao Chen;Qiong Chen;Wenchao Yang;Guangfu Yang
中科院分区：
文献类型：
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作者：
Da-Wei Wang;Hong-Yan Lin;Bo He;Feng-Xu Wu;Tao Chen;Qiong Chen;Wenchao Yang;Guangfu Yang
4-羟基苯丙酮酸双加氧酶（EC 1.13.11.27，HPPD）是新型漂白除草剂发现的重要靶点。作为发现新型作物选择性 HPPD 抑制剂的持续工作，我们在 CH2Cl2 中使用 N,N'-羰基二咪唑 (CDI)、三乙胺和丙酮合氰化氢，通过高效的一锅法合理设计和合成了一系列 2-(芳氧基乙酰基)环己烷-1,3-二酮。总共合成了 58 种三酮化合物，收率良好至优异。一些三酮在体外表现出有效的拟南芥 HPPD (AtHPPD) 抑制活性。 2-(2-((1-溴萘-2-基)氧基)乙酰基)-3-羟基环己-2-en-1-酮，II-13，在 37.5-150 g ai/ha 剂量下表现出高广谱芽后除草活性，对某些杂草的效力几乎与甲基磺草酮一样。此外，II-13 在 150 g ai/ha 的剂量下对玉米和油菜表现出良好的作物安全性，表明 II-13 可能具有作为除草剂用于玉米和油菜田杂草控制的潜力。 II-13 是第一个对油菜籽表现出良好作物安全性的 HPPD 抑制剂。
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-(2-((1-Bromonaphthalen-2-yl)oxy)acetyl)-3-hydroxycyclohex-2-en-1-one, II-13, displayed high, broad-spectrum, and postemergent herbicidal activity at the dosage of 37.5-150 g ai/ha, nearly as potent as mesotrione against some weeds. Furthermore, II-13 showed good crop safety against maize and canola at the rate of 150 g ai/ha, indicating that II-13 might have potential as a herbicide for weed control in maize and canola fields. II-13 is the first HPPD inhibitor showing good crop safety toward canola.