5-(1-氨基-2-苯氧亚乙基)巴比妥酸衍生物的合成及除草活性研究

Synthesis and Herbicidal Activity of 5-(1-Amino-2-phenoxyethylidene)barbituric Acid Derivatives

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.

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)-ethylidene)-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.