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2020 , Vol. 40 >Issue 3: 787 - 793

DOI: https://doi.org/10.6023/cjoc201908024

研究简报

N-(2-(5-(3-溴-1-(3-氯吡啶-2-基)-1H-吡唑-5-基)-1,3,4-噁二唑-2-基)-4-氯-6-甲基苯基)酰胺类新化合物的合成及生物活性

  • 张燕 ,
  • 尚俊峰 ,
  • 李欢 ,
  • 刘航 ,
  • 宋海斌 ,
  • 王宝雷 ,
  • 李正名
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  • 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: 2019-08-16

  修回日期: 2019-10-09

  网络出版日期: 2019-11-07

基金资助

天津市自然科学基金（No.17JCYBJC19900）、国家自然科学基金（No.21772103）和国家重点研发计划（Nos.2017YFD0200505，2018YFD0200100）资助项目.

收起

Synthesis and Biological Activities of Novel N-(2-(5-(3-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl)-1,3,4-oxadiazol-2-yl)-4-chloro-6-methylphenyl) Amides

  • Zhang Yan ,
  • Shang Junfeng ,
  • Li Huan ,
  • Liu Hang ,
  • Song Haibin ,
  • Wang Baolei ,
  • Li Zhengming
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  • State Key Laboratory of Elemento-organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071

Received date: 2019-08-16

  Revised date: 2019-10-09

  Online published: 2019-11-07

Supported by

Project supported by the Natural Science Foundation of Tianjin City (No. 17JCYBJC19900), the National Natural Science Foundation of China (No. 21772103) and the National Key Research and Development Program of China (Nos. 2017YFD0200505, 2018YFD0200100).

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摘要

以N-吡啶基吡唑甲酸和2-氨基-3-甲基苯甲酸为起始原料，经由亲核加成、环化和酰化等多步反应合成了一系列结构新颖的N-（2-（5-（3-溴-1-（3-氯吡啶-2-基）-1H-吡唑-5-基）-1，3，4-噁二唑-2-基）-4-氯-6-甲基苯基）酰胺类化合物.测试了所合成化合物的杀虫及抑菌活性，结果表明，新化合物大多化合物在200 mg·L－1浓度下对东方粘虫（Mythimna separata Walker）具有一定的杀虫活性，尤其是N-（2-（5-（3-溴-1-（3-氯吡啶-2-基）-1H-吡唑-5-基）-1，3，4-噁二唑-2-基）-4-氯-6-甲基苯基）乙酰胺（8a）和N-（2-（5-（3-溴-1-（3-氯吡啶-2-基）-1H-吡唑-5-基）-1，3，4-噁二唑-2-基）-4-氯-6-甲基苯基）-3-氯-2，2-二甲基丙酰胺（8e）致死率可达70%；部分化合物在50 mg·L－1浓度下对油菜菌核病菌的抑菌活性相对较好（54.5%～63.6%），优于triadimefon和chlorantraniliprole；部分化合物如N-（2-（5-（3-溴-1-（3-氯吡啶-2-基）-1H-吡唑-5-基）-1，3，4-噁二唑-2-基）-4-氯-6-甲基苯基）-3，3-二甲基丁酰胺（8f）和N-（2-（5-（3-溴-1-（3-氯吡啶-2-基）-1H-吡唑-5-基）-1，3，4-噁二唑-2-基）-4-氯-6-甲基苯基）-4-氟苯甲酰胺（8h）对苹果轮纹病菌具有中等抑菌活性.值得注意的是，化合物8e的杀粘虫活性和对油菜菌核病菌的抑菌活性都较为突出，可用作新农药创制研究的新型参考结构.

关键词： N-吡啶基吡唑衍生物; 1,3,4-噁二唑; 合成; 杀虫活性; 抑菌活性

本文引用格式

张燕 , 尚俊峰 , 李欢 , 刘航 , 宋海斌 , 王宝雷 , 李正名 . N-(2-(5-(3-溴-1-(3-氯吡啶-2-基)-1H-吡唑-5-基)-1,3,4-噁二唑-2-基)-4-氯-6-甲基苯基)酰胺类新化合物的合成及生物活性[J]. 有机化学, 2020 , 40(3) : 787 -793 . DOI: 10.6023/cjoc201908024

Abstract

A series of novel aromatic amide compounds with N-pyridylpyrazole and 1,3,4-oxadiazole heterocyclic motifs were successfully synthesized with N-pyridylpyrazole carboxylic acid and 2-amino-3-methylbenzoic acid as the starting materials, via multi-step reactions of nucleophilic addition, cyclization, acylation, etc. The preliminary bioassay tests indicated that most of these compounds have apparent insecticidal activities, among which compounds N-(2-(5-(3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl)-1,3,4-oxadiazol-2-yl)-4-chloro-6-methylphenyl)acetamide (8a) and N-(2-(5-(3-bromo-1-(3-chloro-pyridin-2-yl)-1H-pyrazol-5-yl)-1,3,4-oxadiazol-2-yl)-4-chloro-6-methylphenyl)-3-chloro-2,2-dimethylpropanamide (8e) possessed a mortality rate of 70% towards Mythimna separata Walker at the concentration of 200 mg·L-1. Some of the compounds exhibited good fungicidal activities at 50 mg·L-1 against Sclerotinia sclerotiorum with the growth inhibitory rates of 54.5%~63.6%, which is more effective than the controls of triadimefon and chlorantraniliprole. Several compounds such as N-(2-(5-(3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl)-1,3,4-oxadiazol-2-yl)-4-chloro-6-methylphenyl)pivalamide (8f) and N-(2-(5-(3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl)-1,3,4-oxadiazol-2-yl)-4-chloro-6-methylphenyl)-4-fluoroben-zamide (8h) showed moderate fungicidal activity against Physalospora piricola. It is worth noting that compound 8e, which has favorable insecticidal and fungicidal activities towards Mythimna separata Walker and Sclerotinia sclerotiorum respectively, could be used as novel reference structure for new agrochemical innovations.

Key words： N-pyridylpyrazole derivatives; 1,3,4-oxadiazole; synthesis; insecticidal activity; fungicidal activity

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