Citation: Shang Junfeng, Liu Qiaoxia, Wang Baolei, Li Zhengming. Synthesis and Biological Activities of Novel N-Substitutedphenyl-2-pyrazolylnicotinamides[J]. Chinese Journal of Organic Chemistry, ;2019, 39(5): 1489-1496. doi: 10.6023/cjoc201810025 shu

Synthesis and Biological Activities of Novel N-Substitutedphenyl-2-pyrazolylnicotinamides

State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Enginneering(Tianjin), College of Chemistry, Nankai University, Tianjin 300071

Corresponding author: Wang Baolei, nkwbl@nankai.edu.cn Li Zhengming, nkzml@vip.163.com
Received Date: 19 October 2018
Revised Date: 3 December 2018
Available Online: 18 May 2019
Fund Project: Project supported by the National Key Research and Development Program of China (Nos. 2017YFD0200505, 2018YFD0200100), the National Natural Science Foundation of China (No. 21772103) and the Natural Science Foundation of Tianjin City (No. 17JCYBJC19900)the National Key Research and Development Program of China 2017YFD0200505the Natural Science Foundation of Tianjin City 17JCYBJC19900the National Key Research and Development Program of China 2018YFD0200100the National Natural Science Foundation of China 21772103

Figures(4)

Based on the agrochemical structure of anthranilic diamides, fourteen novel N-substitutedphenyl-2-pyrazolyl- nicotinamides were conveniently synthesized with 2-chloro-3-cyanopyridine and 4-bromopyrazole or 3, 5-dimethylpyrazole as starting materials, via an "acyl transposing" design strategy. Their structures were characterized by 1H NMR, 13C NMR and HRMS. The preliminary bioassay tests indicated that most of these compounds exhibited obvious insecticidal activity at the test concentration of 200 mg/L, among which N-(4-chloro-2-(ethylcarbamoyl)-6-methylphenyl)-2-(3, 5-dimethyl-1H-pyra- zol-1-yl)nicotinamide (Il) possessed a 70% mortality rate against Mythimna separata Walker; some of the compounds displayed favorable fungicidal activities at 50 mg/L towards Physalospora piricola and Alternaria solani Sorauer, especially 2-(4-bromo-1H-pyrazol-1-yl)-N-(2-(cyclopropylcarbamoyl)-4-iodo-6-methylphenyl)nicotinamide (If) and 2-(4-bromo-1H- pyrazol-1-yl)-N-(4-chloro-2-(ethylcarbamoyl)-6-methylphenyl)nicotinamide (Ih) against Physalospora piricola, and 2-(4- bromo-1H-pyrazol-1-yl)-N-(4-chloro-2-(propylcarbamoyl)phenyl)nicotinamide (Id) against Alternaria solani Sorauer had growth inhibitory rates of 62.9%, 54.3% and 54.5%, respectively. These research results provide important reference for the further study of novel 2-pyrazolylnicotinamide derivatives.
- 2-pyrazolylnicotinamides,
- synthesis,
- insecticidal activity,
- fungicidal activity
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