摘要/Abstract
基于具有生物活性的烯胺二酮骨架及前期报道的先导化合物5-酰基巴比妥酸I的结构, 设计、合成了26个结构新颖的5-(1-氨基-2-苯氧亚乙基)巴比妥酸衍生物. 生物活性测试结果表明, 化合物5-(2-(2-氯-4-氟苯氧基)-1-(戊基氨基)亚乙基)-1,3-二甲基嘧啶-2,4,6(1H,3H,5H)-三酮(APB-5)在苗后处理, 187.5 g?ha–1剂量时, 对双子叶植物(油菜、苋菜)具有100%的抑制活性. 更重要的是, 化合物APB-5在375 g?ha–1的剂量时具有宽的除草谱且对玉米、小麦和谷子安全, 这说明该化合物具有成为除草剂的潜力. 此外, 通过研究拟南芥的表型及化合物对激素响应基因的影响发现, 化合物APB-5具有与激素类除草剂2,4-二氯苯氧乙酸(2,4-D)相似的作用机制. 目前的研究表明, 化合物APB-5可以作为进一步开发新型生长素类除草剂的先导结构.
关键词: 巴比妥酸, 烯胺二酮, 合成, 除草活性, 激素
Based on the bioactive enamino diketone skeleton and the structure of our previously reported lead compound 5-acylbarbituric acid I, twenty-six novel 5-(1-amino-2-phenoxyethylidene)barbituric acid derivatives were designed and synthesized. The bioassay results showed that the analog 5-(2-(2-chloro-4-fluorophenoxy)-1-(pentylamino)-ethyli- dene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione (APB-5) displayed excellent post-emergent herbicidal activity, with inhibition 100% against dicotyledonous plants (Brassica campestris, Amaranthus retroflexus), even at a dosage of 187.5 g? ha–1. More importantly, compound APB-5 showed a broad spectrum of weed control and displayed good crop safety toward wheat, maize and millet, when applied at 375 g?ha–1, indicating its remarkable potential as a herbicide. Furthermore, by investigating the phenotypes of Arabidopsis thaliana and analyzing the effect of compound APB-5 on auxin response genes in plants, it was found that compound APB-5 had a herbicidal mechanism similar to auxin-type herbicides, such as 2,4-dichlorophenoxyacetic acid (2,4-D). Taken together, the present work demonstrated that compound APB-5 could serve as a lead structure for further developing novel auxin-type herbicides.
Key words: barbituric acid, enamino diketone, synthesis, herbicidal activity, auxin
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