摘要
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.
作者
王超超
刘会
赵微
李攀
冀庐莎
柳仁民
雷康
徐效华
Wang Chaochao;Liu Hui;Zhao Wei;Li Pan;Ji Lusha;Liu Renmin;Lei Kang;Xu Xiaohua(School of Pharmacy,Liaocheng University,Liaocheng 252000;College of Life Sciences,Liaocheng University,Liaochen 252000;State Key Laboratory of Elemento-organic Chemistry,Nankai University,Tianjin 300071)
出处
《有机化学》
SCIE
CAS
CSCD
北大核心
2021年第5期2063-2073,共11页
Chinese Journal of Organic Chemistry
基金
国家自然科学基金(No.31701827)
中国博士后科学基金(No.2020M671984)
聊城大学博士科研启动基金(No.318051647)
聊城大学大学生创新创业训练(No.CXCY2020Y179)
山东省自然科学基金(No.ZR2019PC041)资助项目.
关键词
巴比妥酸
烯胺二酮
合成
除草活性
激素
barbituric acid
enamino diketone
synthesis
herbicidal activity
auxin