Chinese Journal of Organic Chemistry >
Design, Synthesis and Bioactivity Research of Novel Bipyridine Compounds
Received date: 2024-06-21
Revised date: 2024-07-24
Online published: 2024-08-19
Supported by
National Natural Science Foundation of China(22277136); National Natural Science Foundation of China(22077137)
Pyridines play an important role in the design of pesticides. Flupyrimin (FLP) is a novel nicotine insecticide with bipyridine structure. Previously, our research found that bipyridine compound N-((6-chloropyridin-3-yl)methyl)-3-methyl- N-(pyridin-2-yl)benzenesulfonamide (3c) had certain insecticidal activity following structural modifications on FLP. In this paper, using 3c as the lead compound, a series of novel bipyridine derivatives were designed and synthesized. Bioactivity assay results revealed that target compounds exhibited some insecticidal and antifungal activities. Among them, N-((6-chloropyridin- 3-yl)methyl)-N-methylpyridin-2-amine (T1) and N-((6-chloropyridin-3-yl)methyl)-N-ethylpyridin-2-amine (T2) showed good insecticidal activity against A. glycines, with LC50 values of 11.04 mg/L and 25.12 mg/L, respectively. N-((6-Chloropyridin-3- yl)methyl)-N-pentylpyridin-2-amine (T5) and N-((6-chloropyridin-3-yl)methyl)-N-hexylpyridin-2-amine (T6) displayed good antifungal activity against B. cinerea with EC50 values of 7.45 mg/L and 10.54 mg/L, respectively. The bee toxicity test results revealed that compound T1 is safe for Apis mellifera. Furthermore, molecular dynamics simulations elucidated the insecticidal mechanism of compound T1, revealing its stable formation of water relaying hydrogen-bond interaction network with key amino acids of AChBP, and a superior binding free energy compared to 3c. This study provides a good significance for exploring the agricultural biological activity of pyridine compounds.
Xingxing Lu , Yufan Lin , Huan Xu , Xiaoming Zhang , Xuesheng Li , Yun Ling , Xinling Yang . Design, Synthesis and Bioactivity Research of Novel Bipyridine Compounds[J]. Chinese Journal of Organic Chemistry, 2025 , 45(1) : 276 -285 . DOI: 10.6023/cjoc202405010
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