高等学校化学学报 ›› 2015, Vol. 36 ›› Issue (4): 672-681.doi: 10.7503/cjcu20140955

• 有机化学 • 上一篇    下一篇

新型含苯基取代嘧啶基磺酰脲衍生物的设计、 合成及生物活性

陈伟1, 魏巍1, 周莎1, 李永红1, 张晓1, 童军2, 李玉新1(), 李正名1()   

  1. 1. 南开大学元素有机化学国家重点实验室, 化学化工协同创新中心(天津)
    2. 农药国家工程研究中心, 天津 300071
  • 收稿日期:2014-10-27 出版日期:2015-04-10 发布日期:2015-03-27
  • 作者简介:联系人简介: 李正名, 男, 博士, 教授, 中国工程院院士, 主要从事有机化学和农药化学研究.E-mail: nkzml@vip.163.com. 李玉新, 女, 博士, 副研究员, 主要从事绿色农药化学和有机合成化学研究. E-mail: liyx128@nankai.edu.cn
  • 基金资助:
    国家自然科学基金(批准号: 21272129)和“十二五”国家科技支撑计划项目(批准号: 2011BAE06B05)资助

Design, Synthesis and Biological Activity of Novel Sulfonylurea Derivatives Containing Phenyl-substituted Pyrimidine Moiety

CHEN Wei1, WEI Wei1, ZHOU Sha1, LI Yonghong1, ZHANG Xiao1, TONG Jun2, LI Yuxin1,*(), LI Zhengming1,*()   

  1. 1. State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering(Tianjin)
    2. National Pesticide Engineering Research Center, Nankai University, Tianjin 300071, China
  • Received:2014-10-27 Online:2015-04-10 Published:2015-03-27
  • Contact: LI Yuxin,LI Zhengming E-mail:liyx128@nankai.edu.cn;nkzml@vip.163.com
  • Supported by:
    † Supported by the National Natural Scinece Foundation of China(No.21272129) and the National Key Technologies Research and Development Program of China(No.2011BAE06B05)

摘要:

将苯基引入到嘧啶环的4位, 设计、 合成了2个系列共24个结构新颖的磺酰脲类衍生物, 并对其生物活性进行了研究. 抑菌实验结果表明, 目标化合物对苹果轮纹病菌和小麦纹枯病菌表现出优异的抑制率, 其中化合物9f对5种病菌的抑制率均超过65%. 进一步研究发现, 化合物9f对苹果轮纹病菌的EC50值为8.63 mg/L, 略高于对照药百菌清(7.33 mg/L); 化合物8k和9k对小麦纹枯病菌的EC50值分别为5.48和6.09 mg/L, 与百菌清(4.26 mg/L)接近. 同时, 盆栽法除草测试结果表明, 在75 g/ha剂量下, 化合物8d和9d对油菜具有较好的芽前除草活性, 分别为86%和73%; 化合物9h对反枝苋的土壤处理抑制活性为100%, 优于对照药氯磺隆(96%).

关键词: 磺酰脲, 乙酰乳酸合成酶, 苯基取代嘧啶, 抑菌活性, 除草活性

Abstract:

Acetolactate synthase(ALS) has been regarded as an attractive target for fungicide and herbicide discovery. Furthermore, sulfonylurea(SU) as one of the most active ALS inhibitors were used as herbicides in crops protect. In order to discuss the multi-biological activity of SU, two series of novel SU derivatives containing phenyl-substituted pyrimidine moiety were designed, synthesized and their antifungal activity and herbicidal activity were evaluated. The bioassay results indicated that some title compounds showed excellent antifungal activity against Physalospora piricola and Rhizoctonia cerealis in vitro at the dosage of 50 mg/L. Particularly, compound 9f exhibited more than 65% inhibitory activity against five phytopathogens. On the basis of advanced screening test, the EC50 value of compound 8f against P. piricola was 8.63 mg/L, which was a little higher than Chlorothalonil(EC50=7.33 mg/L), the EC50 value of compounds 8k(5.48 mg/L) and 9k(6.09 mg/L) against R. cerealis were similar to Chlorothalonil(EC50=4.26 mg/L). In addtion, the title compounds showed favorable pre-emergence treatment herbicidal activity against Brassica napus and Amaranthus retroflexus at the dosage of 75 g/ha. For example, compounds 8d and 9d showed 86% and 73% inhibition activity respectively against Brassica napus; compound 9h exhibited 100% herbicidal activity against Amaranthus retroflexus, which was better than that of Chlorsulfuron(96%). The results provided useful information for designing new SU with highly fungicidal activity and herbicidal activity.

Key words: Sulfonylurea, Acetolactate synthase, Phenyl-subsituted pyrimidine, Antifungal activity, Herbicidal activity

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