Efficient Total Synthesis and Herbicidal Activity of 3-Acyltetramic Acids: Endogenous Abscisic Acid Synthesis Regulators
Efficient Total Synthesis and Herbicidal Activity of 3-Acyltetramic Acids: Endogenous Abscisic Acid Synthesis Regulators
复制标题
3-酰基四胺酸的高效全合成和除草活性：内源性脱落酸合成调节剂
DOI：
10.1021/acs.jafc.2c04382
复制
发表时间：
2022-10-17
影响因子：
6.1
通讯作者：
Hua, Rimao
中科院分区：
文献类型：
--
作者：
Liu, Xiankun;Wen, Shiqiang;Hua, Rimao
一种有效的合成方法将允许大量的特特拉姆酸类似物被合成的性质和效力的优化。本文报道了一种简便、有效的合成3-酰基特特拉姆酸的方法。合成主要通过（1）温和的分子内环化和（2）亲核试剂与酰基Meldrum酸之间形成β-酮酰胺来完成。3-乙酰特特拉姆酸对稗草和马齿苋具有一定的毒性。在750 g ha ~（-1）剂量下，6 k和6a对E.马唐、紫花马唐、反枝苋。6 K抑制内源脱落酸的合成，从而抑制幼苗的萌发和植株的生长。不同的酰基Meldrum酸和氨基酸酯的引入适用于3-酰基特特拉姆酸的平行合成。作用机理和除草活性研究表明，3-特特拉姆酸具有良好的除草性能，是一种很有前途的除草剂候选物。该研究将为新型除草剂的开发提供参考。
An efficient synthesis method will allow a large number of tetramic acid analogues to be synthesized for property and potency optimization. In this study, a facile and efficient method was described for the synthesis of 3-acyltetramic acids. The synthesis was accomplished mainly via (1) mild intramolecular cyclization and (2) the formation of beta-ketoamides between nucleophiles and acyl Meldrum's acids. 3-Acyltetramic acid exhibited phytotoxicity against Echinochloa crusgalli and Portulaca oleracea. At a dosage of 750 g ha-1, 6k and 6a showed high herbicidal activity against E. crusgalli, Digitaria sanguinalis and P. oleracea, Amaranthus retroflexus, respectively. 6k inhibited the synthesis of endogenous abscisic acid, thus seedling germination and plant growth. The incorporation of various acyl Meldrum's acids and amino acid esters was applicable to the parallel synthesis of 3-acyltetramic acids. The mode of action and herbicidal activity indicate that 3-tetramic acid had good herbicidal performance and was a promising herbicide candidate. This study will provide a reference for novel herbicide development.