de Faria Kamylla C F, Alvarenga Elson S, Oliveira Denilson F, Baia Vitor C, Isenmann Armin F
Department of Chemistry, Universidade Federal de Viçosa, Viçosa 36570-900, MG, Brazil.
Department of Chemistry, Universidade Federal de Lavras, Lavras 37203-202, MG, Brazil.
Plants (Basel). 2025 Jun 24;14(13):1933. doi: 10.3390/plants14131933.
Chemical control is key to minimizing agricultural losses, driving the search for more efficient and selective herbicides. This study reports the synthesis of epoxyoxirenes, their phytotoxic evaluation, and an analysis to identify the protein target of the most active compound in plants. Compounds 2-19 were tested on spp., spp., spp., , and . The synthetic route began with anhydride , obtained via a Diels-Alder reaction between maleic anhydride and furan (91% yield). Anhydride was converted into amides - through reactions with aromatic amines (>92% yields), followed by cyclization to imides - (60-83% yields), and subsequent epoxidation to afford epoxides - (62-98% yields). All the compounds interfered with seedling development, with compounds - showing the greatest phytotoxicity to at concentrations of 500 μM and 1000 μM. An analysis suggested plant tubulin as a potential protein target for the most active compounds. These findings highlight epoxyoxirenes as promising scaffolds for novel herbicide development and support further investigation into their mechanism of action.
化学防治是将农业损失降至最低的关键，这推动了人们对更高效、更具选择性的除草剂的探索。本研究报告了环氧氧杂环丁二烯的合成、它们的植物毒性评估，以及对植物中最具活性化合物的蛋白质靶点进行的分析。化合物2 - 19在[具体植物种类1]、[具体植物种类2]、[具体植物种类3]、[具体植物种类4]和[具体植物种类5]上进行了测试。合成路线始于酸酐[具体酸酐名称]，它是通过马来酸酐与呋喃之间的狄尔斯 - 阿尔德反应获得的（产率91%）。酸酐[具体酸酐名称]通过与芳香胺反应转化为酰胺[具体酰胺名称]（产率>92%），随后环化生成酰亚胺[具体酰亚胺名称]（产率60 - 83%），并随后进行环氧化得到环氧化物[具体环氧化物名称]（产率62 - 98%）。所有化合物都干扰了幼苗发育，化合物[具体化合物名称]在500 μM和1000 μM浓度下对[具体植物种类]表现出最大的植物毒性。一项[具体分析方法]分析表明，植物微管蛋白是最具活性化合物的潜在蛋白质靶点。这些发现突出了环氧氧杂环丁二烯作为新型除草剂开发的有前景的骨架，并支持对其作用机制进行进一步研究。
