有机化学 ›› 2016, Vol. 36 ›› Issue (5): 1051-1059.DOI: 10.6023/cjoc201510019 上一篇    下一篇

研究论文

N-叔丁基-N'-氟代苯甲酰基-取代吡啶甲酰肼衍生物的合成与杀虫活性研究

胡崇波, 刘建华, 杜晓华   

  1. 浙江工业大学催化加氢中心 浙江省绿色农药清洁生产技术研究重点实验室 浙江省绿色农药协同创新中心 杭州 310014
  • 收稿日期:2015-10-17 修回日期:2015-12-15 发布日期:2016-01-21
  • 通讯作者: 杜晓华 E-mail:duxiaohua@zjut.edu.cn

Synthesis and Insecticidal Activities of N-(tert-Butyl)-N'-fluorobenzoyl-substitutedpyridylcarbonyl Hydrazide Derivatives

Hu Chongbo, Liu Jianhua, Du Xiaohua   

  1. Zhejiang Key Laboratory of Green Pesticides and Cleaner Production Technology, Zhejiang Green Pesticide Collaborative Innovation Center, Catalytic Hydrogenation Research Center, Zhejiang University of Technology, Hangzhou 310014
  • Received:2015-10-17 Revised:2015-12-15 Published:2016-01-21

为改进双酰肼类杀虫剂的性能,将氟代苯基和吡啶环同时引入双酰肼的基本结构中,设计合成了20个新型的N-叔丁基-N'-氟代苯甲酰基-取代吡啶甲酰肼衍生物,经1H NMR、13C NMR、IR和HRMS确证了分子结构.生物活性测试表明,在浓度为500mg/L时,大部分化合物对粘虫(Mythimna separata)的致死率都达到80%以上.其中N-叔丁基-N'-(2,6-二氟苯甲酰基)-2-氯烟酰肼(6bb)和N-叔丁基-N'-(2,6-二氟苯甲酰基)-2,5-二氯烟酰肼(6gb)在浓度为10mg/L时对粘虫的致死率分别为100%和80%.化合物6bb对东方粘虫的半致死浓度(LC50值)为8.77mg/L,对东方粘虫的毒力约为虫酰肼的0.51倍,对小菜蛾(Plutella xylostella)的毒力为虫酰肼的1.5倍.

关键词: 双酰肼, 吡啶甲酰肼, 合成, 杀虫活性

In order to find novel diacylhydrazine derivatives which possessed high activities against pests, 20 novel N-(tert-butyl)-N'-fluorobenzoyl-substitutedpyridylcarbonyl hydrazide derivatives were synthesized by introducing fluoro-contained phenyl and pyridine into the basic structure of diacylhydrazines. Their structures were confirmed by 1H NMR, 13C NMR, IR and HRMS. The bioassay results indicated that most of the compounds exhibited more than 80% mortality against Mythimna separateat the concentration of 500 mg/L. Among these compounds, N-(tert-butyl)-N'-(2,6-difluorobenzoyl)-N-2-chloronico-tinohydrazine (6bb)andN-(tert-butyl)-N'-(2,6-difluorobenzoyl)-N-2,5-dichloronicotinohydrazine (6gb)exhibited 100% and 80% mortality against Mythimna separateat 10 mg/L, respectively. The LC50 of compound 6bb against Mythimna separatawas 8.77 mg/L, and it showed about 0.51 times of toxicity against Mythimna separatethan tebufenozide and had 1.5 times of toxicity against Plutella xylostella than tebufenozide.

Key words: diacylhydrazine, pyridylcarbonyl hydraziden, synthesis, insecticidal activity