摘要
乙酰羟基酸合成酶(Acetohydroxyacid synthase,AHAS,EC4.1.3.18)是植物和微生物中亮氨酸、异亮氨酸和缬氨酸合成途径的一个关键酶,以AHAS为靶标的磺酰脲类除草剂具有高效、高选择性和对环境友好的特点.通过2-氨基-4-甲基嘧啶溴代反应以及进一步的衍生、磺酰基异氰酸酯的胺解,合成了一系列含有5-溴嘧啶基的新磺酰脲.其结构经1HNMR、质谱和元素分析确定.生物活性测试表明目标化合物在离体水平对大肠杆菌乙酰羟基酸合成酶同工酶AHASII表现出了与市售除草剂苯磺隆相当甚至更优的抑制活性,而盆栽除草活性低于苯磺隆.
Acetohydroxy acid synthase (AHAS) catalyzes the key reactions in the biosynthesis pathways of branched-chain amino acids (valine, isoleucine and leucine) in plants and microorganisms, and sulfonylurea herbicides are inhibitors of AHAS, characterized by high herbicidal activity, high degree of selectivity, and excellent environmental safety. A series of 5-bromopyrimidinyl-containing new sulfonylureas have been synthesized through bromination of 2-amino-4-methyl pyrimidine, followed by further modification and then coupled with sulfonyl isocyanate. Their structures were confirmed by 1H NMR, MS techniques and elemental analysis. Preliminary bioassay of sulfonylureas showed that the title compounds exhibited good in vitro activities against E. coli acetohydroxy acid synthase isoenzyme AHASII but showed lower herbicidal activities in vivo, compared with commercial herbicide tribenuron-methly.
出处
《有机化学》
SCIE
CAS
CSCD
北大核心
2010年第4期564-568,共5页
Chinese Journal of Organic Chemistry
基金
国家自然科学基金(No.20432010)
国家重点基础研究发展计划(973计划
No.2003CB114403)
科技部国际合作(2008DFA30770)
教育部科学技术研究重点(重大)(No.104189)
山西省青年科学研究基金(No.2009021041-1)资助项目