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Chinese Journal of Organic Chemistry >

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

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

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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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

Cite this article

Zhang Yan , Shang Junfeng , Li Huan , Liu Hang , Song Haibin , Wang Baolei , Li Zhengming . 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[J]. Chinese Journal of Organic Chemistry, 2020 , 40(3) : 787 -793 . DOI: 10.6023/cjoc201908024

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