有机化学 ›› 2018, Vol. 38 ›› Issue (5): 1214-1222.DOI: 10.6023/cjoc201712019 上一篇    下一篇

研究论文

含酰胺结构的4"-阿维菌素三唑类衍生物的合成及杀虫活性

孙国绍, 张晶晶, 金淑惠, 张建军   

  1. 中国农业大学理学院 北京 100193
  • 收稿日期:2017-12-12 修回日期:2018-01-05 出版日期:2018-05-25 发布日期:2018-01-10
  • 通讯作者: 金淑惠,E-mail:shuhuij@cau.edu.cn;张建军,E-mail:zhangjianjun@cau.edu.cn E-mail:shuhuij@cau.edu.cn;zhangjianjun@cau.edu.cn
  • 基金资助:

    国家自然科学基金(No.21772230)资助项目.

Synthesis and Insecticidal Activity of 4"-Avermectin Triazole Derivatives Containing Amide Unit

Sun Guoshao, Zhang Jingjing, Jin Shuhui, Zhang Jianjun   

  1. College of Science, China Agricultural University, Beijing 100193
  • Received:2017-12-12 Revised:2018-01-05 Online:2018-05-25 Published:2018-01-10
  • Contact: 10.6023/cjoc201712019 E-mail:shuhuij@cau.edu.cn;zhangjianjun@cau.edu.cn
  • Supported by:

    Project supported by the National Natural Science Fondation of China (No. 21772230).

根据活性亚结构拼接原理,以阿维菌素B1a为先导化合物,经过酰胺化和点击反应合成了一系列含酰胺结构的4"-阿维菌素三唑类衍生物,并通过1H NMR、13C NMR和高分辨质谱对目标化合物进行结构表征.初步的生物活性测定结果表明,目标化合物对朱砂叶螨、桃蚜和秀丽隐杆线虫均具有一定的杀虫活性.在0.1μg/mL浓度下,4"-(1-(4-(2-(4-氯苯基)-3-甲基丁酰胺基)-1H-1,2,3-三唑基)乙酰胺基)阿维菌素B1a(11b)和4"-(1-(4-氯苯甲酰胺基)-1H-1,2,3-三唑基)乙酰胺基)阿维菌素B1a(11e)对朱砂叶螨的杀虫活性达到83.5%和81.2%;4"-(1-(2-氨基-3-甲基苯乙酰胺基)-1H-1,2,3-三唑基)乙酰胺基)阿维菌素B1a(11i)对桃蚜(c:50 μg/mL)和秀丽隐杆线虫(1 μg/mL)的杀虫活性分别为86.4%和74.6%,优于对照药阿维菌素B1a.

关键词: 酰胺, 1,2,3-三唑, 阿维菌素B1a, 杀虫活性

Based on avermectin structure framework, a series of novel 4"-avermectin triazole derivatives containing amide unit were synthesized via the method of click reaction and amidation. The structures of target compounds were fully characterized by 1H NMR, 13C NMR and HRMS. The preliminary bioassay showed that the target compounds possessed certain insceticidal activities against Tetranychus cinnabarinus, Myzus persicae and Caenorhabditis elegans. At the concentration of 0.1 μg/mL, the lethal rates of 4"-(1-(4-(2-(4-chlorphenyl)-3-methylbutylamido)-1H-1, 2, 3-triazolyl)acetamido)avermectin B1a (11b) and 4"-(1-(4-chlorobenzoamido)-1H-1, 2, 3-triazolyl)acetamido)avermectin B1a (11e) against Tetranychus cinnabarinus were 83.5% and 81.2%, respectively, and the lethal rates of 4"-(1-(2-amido-3-methylphenylethylamido)-1H-1, 2, 3- triazolyl)acetamido)avermectin B1a (11i) against Myzus persicae (c=50 μg/mL) and Caenorhabditis elegans (c=1 μg/mL) were 86.4% and 74.6%, which were better than that of avermetcin B1a.

Key words: amide, 1, 2, 3-triazole, avermectin B1a, insecticidal activity