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有机化学
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有机化学 ›› 2010, Vol. 30 ›› Issue (12): 1925-1930. 上一篇    下一篇

研究简报

N -{1-[(6-氯吡啶-3-基)甲基]-5-甲基-1H-1,2,3-三唑-4-甲酰基}-N -叔丁基-N-取代苯甲酰肼的合成与杀虫活性

Khalema, Thandiwe D. L.，石德清   

  1. (华中师范大学化学学院 农药与化学生物学教育部重点实验室 武汉 430079)
  • 收稿日期:2010-04-19 修回日期:2010-06-25 发布日期:2010-07-08
  • 通讯作者: Thandiwe, D. L. Khalema E-mail:Thandiwe7869@yahoo.com
  • 基金资助:

    国家自然科学基金

Synthesis and Insecticidal Activities of N -{1-[(6-Chloropyrid-3-yl)- methyl]-5-methyl-1H-1,2,3-triazol-4-formyl}-N-tert-butyl- N-subsitututedbenzoylhydrazines

Khalema , Thandiwe D. L., SHI De-Qing   

  1. (Key Laboratory of Pesticide and Chemical Biology of Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079)
  • Received:2010-04-19 Revised:2010-06-25 Published:2010-07-08

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双酰肼化合物作为一类重要的昆虫生长调节剂, 已广泛应用于农作物的保护中. 为了发现新颖结构的高效、低毒双酰肼杀虫剂先导化合物, 采用点击化学常用的1,2,3-三唑杂环将新烟碱杀虫剂的药效团2-氯-5-(氯甲基)吡啶引入到双酰肼分子骨架中, 设计并合成了9种未见文献报道的含双杂环结构的双酰肼目标化合物, 其结构经IR, 1H NMR, ESI-MS和元素分析测试技术确证. 初步的生物活性测定结果表明, 部分目标化合物在200 mg/L质量浓度下对小菜蛾(Spodoptera exigua)和甜菜夜蛾(Plutella xylostella)表现出中等程度的杀虫活性|但所有目标化合物在200 mg/L浓度下对蚕豆蚜虫(Aphis fabae)的杀虫活性均较弱.

关键词: 1-[(6-氯吡啶-3-基)甲基]-5-甲基-1H-1,2,3-三唑-4-甲酸, 双酰肼化合物, 杀虫活性

Diacylhydrazine compounds have been widely used as one of the most important insect growth regulators. In order to find novel diacylhydrazine insecticide lead compounds with high activity and low toxicity, a series of novel nitrogen heterocyclic analogues of diacylhydrazine derivatives were designed and synthesized by introduction of 1-[(6-chloropyrid-3-yl)methyl]-5-methyl-1H-1,2,3-triazol-4-yl moiety to the diacylhydrazine molecule skeleton. Their structures of the target compounds 3 were characterized by IR, 1H NMR, ESI-MS techniques and elemental analyses. The results of bioassays showed that some of the title compounds 3 possessed moderate insecticidal activities against Spodoptera exigua and Plutella xylostella larvaes in the concentration of 200 mg/L. Whereas all the title compounds 3 displayed weak insecticidal activity against Aphis in the same concentration.

Key words: 1-[(6-chloropyrid-3-yl)methyl]-5-methyl-1H-1,2,3-triazol-4-formic acid, diacylhydrazine, insecticidal activity