摘要
以N-吡啶基吡唑甲酸乙酯、取代邻氨基苯甲酸为原料,经由还原、氧化、亲核加成、缩合、重氮化等多步反应,合成了一系列3-(((3-溴-1-(3-氯吡啶-2-基)-1H-吡唑-5-基)亚甲基)氨基)取代苯并[d][1,2,3]三嗪-4(3H)-酮类目标化合物.初步生物活性测试结果表明,该系列化合物大多具有一定的杀虫活性,其中一个化合物在200mg·L^-1浓度下对东方粘虫(Mythimna separata Walker)具有70%的致死率;部分化合物表现出显著的抑菌活性,有两个化合物在50mg·L^-1浓度下对苹果轮纹病菌(Physalospora piricola)具有92.3%的抑制率,可作为新型抑菌先导结构,为后续的深入研究提供重要参考.
A series of 3-(((3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl)methylene)amino)substituted-benzo[d][1,2,3]- triazin-4(3H)-ones were synthesized successfully with ethyl N-pyridylpyrazole carboxylate and substituted aminobenzoic acids as starting materials, via multi-step reactions of reduction, oxidation, nucleophilic addition, condensation and diazotization. The preliminary bioassay tests indicated that most of these compounds have certain insecticidal activities, among which one compound showed a mortality rate of 70% towards Mythimna separata Walker at the test concentration of 200 mg·L^-1 , some compounds exhibited favorable fungicidal activities at 50 mg·L^-1 , particularly two compounds which possessed 92.3% growth inhibitory rate against Physalospora piricola, could be used as new fungicidal leading structures for further investigations on this type of compounds.
作者
张燕
朱洪伟
尚俊峰
王宝雷
李正名
Zhang Yan;Zhu Hongwei;Shang Junfeng;Wang Baolei;Li Zhengming(Collaborative Innovation Center of Chemical Science and Enginneering (Tianjin),State Key Laboratory of Elemento-Organic Chemistry,College of Chemistry,Nankai University,Tianjin 300071)
出处
《有机化学》
SCIE
CAS
CSCD
北大核心
2019年第3期861-866,共6页
Chinese Journal of Organic Chemistry
基金
天津市自然科学基金(No.17JCYBJC19900)
国家重点研发计划(No.2017YFD0200505)
国家自然科学基金(No.21772103)资助项目~~
关键词
N-吡啶基吡唑衍生物
苯并三嗪酮
杀虫活性
抑菌活性
构效关系
N-pyridylpyrazole derivatives
benzotriazinone
insecticidal activity
fungicidal activity
structure-activity relationship
