Citation: Shi Yanhua, Zhang Shuai, Wan Fuxian, Sun Changxing, Jiang Lin. Synthesis, Fungicidal Activity and Molecular Docking Study of Novel N-[2-((Substitutedphenyl)amino)pyridin-3-yl]-pyrimidine-4-carboxamides[J]. Chinese Journal of Organic Chemistry, ;2020, 40(7): 1948-1954. doi: 10.6023/cjoc202002019 shu

Synthesis, Fungicidal Activity and Molecular Docking Study of Novel N-[2-((Substitutedphenyl)amino)pyridin-3-yl]-pyrimidine-4-carboxamides

College of Chemistry and Material Science, Shandong Agricultural University, Tai'an, Shandong 271018

Corresponding author: Jiang Lin, jiangl@sdau.edu.cn
Received Date: 17 February 2020
Revised Date: 15 March 2020
Available Online: 10 April 2020
Fund Project: the Natural Science Foundation of Shandong Province ZR2014BM030Project supported by the Natural Science Foundation of Shandong Province (No. ZR2014BM030)

Figures(4)

To explore succinate dehydrogenase inhibitor with new structure, the excellent fungicide boscalid was chosen as a lead compound, and seventeen N-[2-((substitutedphenyl)amino)pyridin-3-yl]-4-methyl-2-(methylthio)pyrimidine-5-carbox-amides (4a~4g) and N-[2-((substitutedphenyl)amino)pyridin-3-yl]-4-methoxy-2-(methylthio)pyrimidine-5-carboxamides (4h~4q) were designed and synthesized. The structures of target compounds were characterized by ¹H NMR, ¹³C NMR, and MALDI-TOF-MS. The in vitro bioassay showed that sixteen compounds possessed high fungicidal activity against S. sclerotiorum with more than 90% inhibitory rate at 50 μg/mL, and some compounds showed moderate activity against B. cinerea at the same dose with inhibitory rate in the range of 70%~84%. The molecular docking study revealed that four hydrogen bonds and one cation-π interaction were formed between N-[2-((3-fluoro-4-methylphenyl)amino)pyridin-3-yl]-4-methoxy-2-(methyl-thio)pyrimidine-5-carboxamide (4p) and succinate dehydrogenase (SDH) enzyme.
- pyrimidine,
- carboxamide,
- synthesis,
- fungicidal activity,
- molecular docking
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