Synthesis and biological evaluation of novel N-pyridylpyrazole derivatives containing 1,2,3-triazole moieties
Based on the commercial insecticide chlorantraniliprole, a series of novel N-pyridylpyrazole derivatives containing 1,2,3-triazole moieties were designed and synthesized via Huisgen cycloaddition reaction. The insecticidal activities of the new compounds against the oriental armyworm (Mythimna separ...
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Published in | Journal of Pesticide Science Vol. 40; no. 3; pp. 138 - 142 |
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Main Authors | , , , , , |
Format | Journal Article |
Language | English |
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Tokyo
Pesticide Science Society of Japan
01.01.2015
Japan Science and Technology Agency |
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Abstract | Based on the commercial insecticide chlorantraniliprole, a series of novel N-pyridylpyrazole derivatives containing 1,2,3-triazole moieties were designed and synthesized via Huisgen cycloaddition reaction. The insecticidal activities of the new compounds against the oriental armyworm (Mythimna separata) were evaluated, of which compound Ib with an N-isopropyl anthranilic amide moiety displayed 100% larvicidal activities against Mythimna separata at a concentration of 10 mg/L. Moreover, the fungicidal activities of some target compounds in vitro against five fungi at 50 µg⁄mL indicated that some compounds exhibited moderate fungicidal activities. |
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AbstractList | Based on the commercial insecticide chlorantraniliprole, a series of novel N-pyridylpyrazole derivatives containing 1,2,3-triazole moieties were designed and synthesized via Huisgen cycloaddition reaction. The insecticidal activities of the new compounds against the oriental armyworm (Mythimna separata) were evaluated, of which compound Ib with an N-isopropyl anthranilic amide moiety displayed 100% larvicidal activities against Mythimna separata at a concentration of 10 mg/L. Moreover, the fungicidal activities of some target compounds in vitro against five fungi at 50 µg/mL indicated that some compounds exhibited moderate fungicidal activities. Based on the commercial insecticide chlorantraniliprole, a series of novel N-pyridylpyrazole derivatives containing 1,2,3-triazole moieties were designed and synthesized via Huisgen cycloaddition reaction. The insecticidal activities of the new compounds against the oriental armyworm (Mythimna separata) were evaluated, of which compound Ib with an N-isopropyl anthranilic amide moiety displayed 100% larvicidal activities against Mythimna separata at a concentration of 10 mg/L. Moreover, the fungicidal activities of some target compounds in vitro against five fungi at 50 mu g/mL indicated that some compounds exhibited moderate fungicidal activities. Based on the commercial insecticide chlorantraniliprole, a series of novel N-pyridylpyrazole derivatives containing 1,2,3-triazole moieties were designed and synthesized via Huisgen cycloaddition reaction. The insecticidal activities of the new compounds against the oriental armyworm (Mythimna separata) were evaluated, of which compound Ib with an N-isopropyl anthranilic amide moiety displayed 100% larvicidal activities against Mythimna separata at a concentration of 10 mg/L. Moreover, the fungicidal activities of some target compounds in vitro against five fungi at 50 μg/mL indicated that some compounds exhibited moderate fungicidal activities. |
Author | Zhang, Xiao Mao, Mingzhen Liu, Qiaoxia Xiong, Lixia Li, Zhengming Li, Yuxin |
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References_xml | – reference: 7) Q. Feng, Z.-L. Liu, L.-X. Xiong, M.-Z. Wang, Y.-Q. Li and Z.-M. Li: J. Agric. Food Chem. 58, 12327–12336 (2010). – reference: 8) Y. Zhao, Y. Q. Li, L. X. Xiong, H. X. Wang and Z. M. Li: Chin. J. Chem. 30, 1748–1758 (2012). – reference: 21) V. V. Rostovtsev, L. G. Green, V. V. Fokin and K. B. Sharpless: Angew. Chem. Int. Ed. 41, 2596–2599 (2002). – reference: 2) G. P. Lahm, D. Cordova and J. D. Barry: Bioorg. Med. Chem. 17, 4127–4133 (2009). – reference: 19) Q. Feng, G. Yu, L. Xiong, M. Wang and Z. Li: Chin. J. Chem. 29, 1651–1655 (2011). – reference: 13) Z. Li, B. Wang, J. Zhang, J. Xu, L. Xiong, Y. Li, Y. Zhao and G. Wang (Nankai University): WO 2012/163095 A1(2012). – reference: 9) M. Mao, Y. Li, Q. Liu, Y. Zhou, X. Zhang, L. Xiong, Y. Li and Z. Li: Bioorg. Med. Chem. Lett. 23, 42–46 (2013). – reference: 15) N. G. Aher, V. S. Pore, N. N. Mishra, A. Kumar, P. K. Shukla, A. Sharma and M. K. Bhat: Bioorg. Med. Chem. Lett. 19, 759–763 (2009). – reference: 20) K. van Alem, G. Belder, G. Lodder and H. Zuilhof: J. Org. Chem. 70, 179–190 (2005). – reference: 1) DuPont Rynaxypyr_insect control Technical Bulletin: http://www2.dupont.com/Production_Agriculture/en_US/assets/downloads/pdfs/ Rynaxypyr_Tech_Bulletin.pdf (Accessd 29 May, 2015) – reference: 10) J. Wu, B.-A. Song, D.-Y. Hu, M. Yue and S. Yang: Pest Manag. Sci. 68, 801–810 (2012). – reference: 11) M.-Z. Mao, Y.-X. Li, Y.-Y. Zhou, X.-L. Zhang, Q.-X. Liu, F.-J. Di, H.-B. Song, L.-X. Xiong, Y.-Q. Li and Z.-M. Li: J. Agric. Food Chem. 62, 1536–1542 (2014). – reference: 16) E. D. Chrysina, É. Bokor, K. Alexacou, M. Charavgi, G. N. Oikonomakos, S. E. Zographos, D. D. Leonidas, N. G. Oikonomakos and L. Somsák: Tetrahedron Asymmetry 20, 733–740 (2009). – reference: 12) G. D. Annis, B. J. Myers, T. P. Selby, T. M. Stevenson and W. T. Zimmerman (E. I. Du Pont de Nemours and Company): WO 2002/048115 A2 (2002). – reference: 4) K. A. Hughes, G. P. Lahm, T. P. Selby and T. M. Stevenson (E. I. Du Pont de Nemours and Company): WO 2004/067528 A1 (2004). – reference: 17) D. Raffa, O. Migliara, B. Maggio, F. Plescia, S. Cascioferro, M. G. Cusimano, G. Tringali, C. Cannizzaro and F. Plescia: Arch. Pharm. 343, 631–638 (2010). – reference: 5) R. G. Hall, O. Loiseleur, J. Pabba, S. Pal, A. Jeanguenat, A. Edmunds and A. Stoller: WO 2009/010260 A2 (2009). – reference: 18) J. L. Randall, R. A. Gibbs, G. K. Bosch, M. D. Curtis, L. Sun and N. Nikolaides: US 2004/0167194 A1 (2004). – reference: 14) G. C. Tron, T. Pirali, R. A. Billington, P. L. Canonico, G. Sorba and A. A. Genazzani: Med. Res. Rev. 28, 278–308 (2008). – reference: 3) B. L. Finkelstein, G. P. Lahm, S. F. McCann, Y. Song and T. M. Stevenson (E. I. Du Pont de Nemours and Company): WO 2003/016284 A1 (2003). – reference: 6) B. Li, D. Xiang, B. Chai, J. Yuan, H. Yang, H. Zhang, H. Wu and H. Yu: (Sinochem Corp., Shenyang Research Institute of Chemcal Industry Co. Ltd.): WO 2008/134969 A1(2008). – ident: 9 doi: 10.1016/j.bmcl.2012.11.045 – ident: 10 doi: 10.1002/ps.2329 – ident: 17 doi: 10.1002/ardp.200900317 – ident: 3 – ident: 18 – ident: 14 doi: 10.1002/med.20107 – ident: 5 – ident: 4 – ident: 1 – ident: 20 doi: 10.1021/jo0487956 – ident: 12 – ident: 11 doi: 10.1021/jf500003d – ident: 19 doi: 10.1002/cjoc.201180295 – ident: 13 – ident: 7 doi: 10.1021/jf102842r – ident: 2 doi: 10.1016/j.bmc.2009.01.018 – ident: 6 – ident: 15 doi: 10.1016/j.bmcl.2008.12.026 – ident: 21 doi: 10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4 – ident: 8 doi: 10.1002/cjoc.201200362 – ident: 16 doi: 10.1016/j.tetasy.2009.03.021 |
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SubjectTerms | 1,2,3-triazole biological activity Insecticides isosterism Mythimna separata N-pyridylpyrazole derivatives |
Title | Synthesis and biological evaluation of novel N-pyridylpyrazole derivatives containing 1,2,3-triazole moieties |
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