School of Pharmacy , Liaocheng University , Liaocheng 252059 , China.
State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry , Nankai University , Tianjin 300071 , China.
J Agric Food Chem. 2019 Sep 18;67(37):10489-10497. doi: 10.1021/acs.jafc.9b03109. Epub 2019 Sep 5.
In order to develop a novel herbicide containing the β-triketone motif, a series of 4-hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one derivatives were designed and synthesized. The bioassay results showed that compound had good pre-emergent herbicidal activity even at a dosage of 187.5 g ha. Moreover, compound showed a broader spectrum of weed control when compared with a commercial herbicide 2,4-dichlorophenoxyacetic acid (2,4-D), and displayed good crop safety to L. and Linn. when applied at 375 g ha under pre-emergence conditions, which indicated its great potential as a herbicide. More importantly, studying the molecular mode of action of compound revealed that the novel triketone structure is a proherbicide of its corresponding phenoxyacetic acid auxin herbicide, which has a herbicidal mechanism similar to that of 2,4-D. The present work indicates that the 4-hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one motif may be a potential lead structure for further development of novel auxin-type herbicides.
为了开发含有β-三酮结构的新型除草剂，设计并合成了一系列 4-羟基-3-(2-苯氧乙酰基)-吡喃-2-酮衍生物。生物测定结果表明，化合物 在 187.5 g/ha 的剂量下仍具有良好的芽前除草活性。与商业除草剂 2,4-二氯苯氧乙酸（2,4-D）相比，化合物 具有更广泛的杂草防治谱，在芽前条件下以 375 g/ha 的剂量施用时对 L. 和 Linn. 表现出良好的作物安全性，这表明其具有作为除草剂的巨大潜力。更重要的是，研究化合物的作用模式表明，新型三酮结构是其相应的苯氧乙酸类生长素除草剂的前体除草剂，其除草机制与 2,4-D 相似。本工作表明，4-羟基-3-(2-苯氧乙酰基)-吡喃-2-酮结构可能是进一步开发新型生长素型除草剂的潜在先导结构。
