有机化学 ›› 2017, Vol. 37 ›› Issue (7): 1774-1780.DOI: 10.6023/cjoc201612030 上一篇    下一篇

研究论文

含2-(取代苯基)噁唑基的邻甲酰胺基苯甲酰胺类化合物合成及杀虫活性研究

王梦梦, 张青青, 岳凯, 李庆山, 徐凤波   

  1. 南开大学化学学院 元素有机化学国家重点实验室 天津 300071
  • 收稿日期:2016-12-07 修回日期:2017-02-22 发布日期:2017-03-08
  • 通讯作者: 李庆山 E-mail:qli@.nankai.edu.cn
  • 基金资助:

    国家自然科学基金(Nos.20772060,21172114)和南开大学元素有机化学国家重点实验室资助项目.

Synthesis and Insecticidal Activity of o-Carboxamidobenzamide Compounds Containing 2-(Substituted phenyl)oxazole Group

Wang Mengmeng, Zhang Qingqing, Yue Kai, Li Qingshan, Xu Fengbo   

  1. State Key Laboratory of Elemento-Organic Chemistry,College of Chemistry,NanKai University,TianJin 300071
  • Received:2016-12-07 Revised:2017-02-22 Published:2017-03-08
  • Contact: 10.6023/cjoc201612030 E-mail:qli@.nankai.edu.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos.20772060,21172114) and the State Key Laboratory of Elemento-Organic Chemistry,Nankai University.

为了研究邻甲酰胺基苯甲酰胺类化合物的杀虫活性,总结该类化合物的构效关系、合成高活性化合物,以2-氨基-3-羟基丙酸与取代2-硝基苯甲酸为原料,经过酯化反应、缩合反应、硝基还原反应、三光气缩合反应等一系列步骤,合成了29个2-(取代苯基)噁唑基的邻甲酰胺基苯甲酰胺类目标化合物,产率在30%~50%之间.根据离体杀东方粘虫活性测定实验结果可知,该类化合物对东方粘虫表现出一定的杀虫活性,其中目标化合物2-(2-溴苯基)-N-(4-氯-2-甲基氨基甲酰基-6-甲基苯基)噁唑-4-甲酰胺(11p)活性最高.通过对目标化合物的结构与杀虫活性的分析,总结出该类化合物的构效关系,筛选出了较高活性的目标化合物.

关键词: 杀虫剂, 邻甲酰胺基苯甲酰胺类化合物, 苯基噁唑基化合物

In order to study the insecticidal activity of o-carboxamidobenzamide compounds, to investigate the structure-activity relationships of these compounds, 2-amino-3-hydroxypropionic acid and substituted 2-nitrobenzoic acid were used as starting materials to synthesize 29 diamides target compounds containing 2-substituted phenyloxazole groups, the yields were in the range of 30% and 50%. The insecticidal activities of these compounds were investigated. To some extend, the title compounds showed insecticidal activity against oriental armyworm (Mythimna separata Walker) in vitro. 2-(2-bromophenyl)-N-(4-chloro-2-(methoxy carbamoyl)-6-methyl phenyl) oxazole-4-carbox-amide (compound 11p) showed the highest insecticidal activity among these compounds. The structure-activity relationship of these compounds was summarized and the compounds with high activity were obtained.

Key words: insecticide, o-carboxamidobenzamide compounds, benzoxazole compounds