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
收稿日期: 2016-12-07
修回日期: 2017-02-22
网络出版日期: 2017-03-08
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
Received date: 2016-12-07
Revised date: 2017-02-22
Online published: 2017-03-08
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
王梦梦 , 张青青 , 岳凯 , 李庆山 , 徐凤波 . 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[J]. 有机化学, 2017 , 37(7) : 1774 -1780 . DOI: 10.6023/cjoc201612030
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.
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