Skip to main content
SpringerLink
Log in

Synthesis, antifungal and insecticidal activity of novel [1,2,4]triazolo[4,3-a]pyridine derivatives containing a sulfide substructure

  • Original Paper
  • Published:
Chemical Papers Aims and scope Submit manuscript

Abstract

A series of [1,2,4]triazolo[4,3-a]pyridine derivatives bearing a sulfide substructure was designed, synthesized and characterized via 1H·NMR, 13C·NMR, IR and elemental analyses. Bioassay Results indicated some of the derivatives displayed good fungicidal activity on Rhizoctonia cerealis, moderated insecticidal activity against Plutella xylostella and good insecticidal activity on Helicoverpa armigera. The inhibitory effects of compounds 4g and 4u against Rhizotonia cerealis were 70.9% at 50 μg mL−1; the IC50 values of compounds 4d and 4s against Plutella xylostella were 43.87 and 50.75 μg mL−1, respectively. And the IC50 values of compounds 4d, 4q, and 4s on Helicoverpa armigera were 58.3, 77.14 and 65.31 μg mL−1, respectively, which were better than that of commercial chlorpyrifos (103.77 μg mL−1).

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1

Similar content being viewed by others

References

  • Bell K, Sunose M, Ellard K, Cansfield A, Taylor J, Miller W, Ramsden N, Bergamini G, Neubauer G (2012) SAR studies around a series of triazolopyridines as potent and selective PI3 K gamma inhibitors. Bioorg Med Chem Lett 22:5257–5263. doi:10.1016/j.bmcl.2012.06.049

    Article  CAS  Google Scholar 

  • Chen YB, Li JL, Shao XS, Xu XY, Li Z (2013) Design, synthesis and insecticidal activity of novel anthranilic diamides with benzyl sulfide scaffold. Chin Chem Lett 24:673–676. doi:10.1016/j.cclet.2013.04.047

    Article  CAS  Google Scholar 

  • Ferguson GD, Delgado M, Plantevin-Krenitsky V, Jensen-Pergakes K, Bates RJ, Torres S, Celeridad M, Brown H, Burnett K, Nadolny L (2016) A novel Triazolopyridine-based spleen tyrosine kinase inhibitor that arrests joint inflammation. Plos One 11:e0145705. doi:10.1371/journal.pone.0145705

    Article  Google Scholar 

  • Ghorab MM, Abdel-Hamide SG, Ali GM, Shaurub ESH (1996) Synthesis and Insecticidal Activity of Some New 3-[4(3H)-Quinazolinone-2-(yl)thiomethyl]-1,2,4-triazole-5-thiols. Pest Sci 48:31–35. doi:10.1002/(SICI)1096-9063(199609)48:1<31:AID-PS430>3.0.CO;2-#

  • Guan LP, Zhang RP, Sun Y, Chang Y, Sul X (2012) Synthesis and studies on the anticonvulsant activity of 5-alkoxy-1,2,4-triazolo[4,3-a]pyridine Derivativesh. Arzneimittelforschung-Drug Res 62:372–377. doi:10.1055/s-0032-1314821

    Article  CAS  Google Scholar 

  • Hua X, Mao W, Fan Z, Ji X, Li F, Zong G, Song H, Li J, Zhou L, Zhou LF, Liang XW, Wang GH, Chen XY (2014) Novel anthranilic diamide insecticides: design, synthesis, and insecticidal evaluation. Aust J Chem 67:1491–1503. doi:10.1071/ch13701

    Article  CAS  Google Scholar 

  • Hua X, Mao W, Fan ZJ, Ji X, Li F, Zong G, Song H, Tatiana K, Morzherin YY, Belskaya NP, Bakulev VA (2016) Design, Synthesis, and Biological Screening of Novel Anthranilic Diamides. J Heterocyclic Chem 53:865–875. doi:10.1002/jhet.2351

    Article  CAS  Google Scholar 

  • Jerome KD, Rucker PV, Xing L, Shieh HS, Baldus JE, Selness SR, Letavic MA, Braganza JF, McClure KF (2010) Continued exploration of the triazolopyridine scaffold as a platform for p38 MAP kinase inhibition. Bioorg Med Chem Lett 20:469–473. doi:10.1016/j.bmcl.2009.11.114

    Article  CAS  Google Scholar 

  • Liu XH, Sun ZH, Yang MY, Tan CX, Weng JQ, Zhang YG, Ma Y (2014) Microwave assistant one pot synthesis, crystal structure, antifungal activities and 3D-QSAR of novel 1,2,4-Triazolo 4,3-a pyridines. Chem Biol Drug Des 84:342–347. doi:10.1111/cbdd.12323

    Article  CAS  Google Scholar 

  • Liu XH, Xu XY, Tan CX, Weng JQ, Xin JH, Chen J (2015) Synthesis, crystal structure, herbicidal activities and 3D-QSAR study of some novel 1,2,4-triazolo[4,3-a]pyridine derivatives. Pest Manag Sci 71:292–301. doi:10.1002/ps.3804

    Article  CAS  Google Scholar 

  • McClure KF, Abramov YA, Laird ER, Barberia JT, Cai W, Carty TJ, Cortina SR, Danley DE, Dipesa AJ, Donahue KM, Dombroski MA, Elliott NC, Gabel CA, Han S, Hynes TR, LeMotte PK, Mansour MN, Marr ES, Letavic MA, Pandit J, Ripin DB, Sweeney FJ, Tan D, Tao Y (2005) Theoretical and experimental design of atypical kinase inhibitors: application to p38 MAP kinase. J Med Chem 48:5728–5737. doi:10.1021/jm050346q

    Article  CAS  Google Scholar 

  • Mokrushina GA, Postovskii IY, Kotovskaya SK (1977) Syntheses of bisheterocycles from 2-hydrazino-3-aminopyridine. Chem Heterocycl Com 13:334–336. doi:10.1007/bf00470323

    Article  Google Scholar 

  • Mu JX, Yang MY, Sun ZH, Tan CX, Weng JQ, Wu HK, Liu XH (2015) Synthesis, crystal structure and DFT studies of 8-chloro-3-((3-chlorobenzyl)thio)-[1,2,4]triazolo[4,3-a]pyridine. Crystals 5:491–500. doi:10.3390/cryst5040491

    Article  CAS  Google Scholar 

  • Mu JX, Shi YX, Wu HK, Sun ZH, Yang MY, Liu XH, Li BJ (2016) Microwave assisted synthesis, antifungal activity, DFT and SAR Study of 1,2,4-triazolo[4,3-a]pyridine derivatives containing hydrazone moieties. Chem Cent J 10:50. doi:10.1186/s13065-016-0196-6

    Article  Google Scholar 

  • Prakash O, Hussain K, Aneja DK, Sharma C, Aneja KR (2011) A facile iodine(III)-mediated synthesis of 3-(3-aryl-1-phenyl-1H-pyrazol-4-yl)-1,2,4-triazolo[4,3-a]pyridines via oxidation of 2-((3-aryl-1-phenyl-1H-pyrazol-4-yl)methylene)-1-(pyridin-2-yl)hydrazine s and their antimicrobial evaluations. Org Med Chem Lett 1:1. doi:10.1186/2191-2858-1-1

    Article  Google Scholar 

  • Sadana AK, Mirza Y, Aneja KR, Prakash O (2003) Hypervalent iodine mediated synthesis of 1-aryl/hetryl-1,2,4-triazolo 4,3-a pyridines and 1-aryl/hetryl 5-methyl-1,2,4-triazolo 4,3-a quinolines as antibacterial agents. Eur J Med Chem 38:533–536. doi:10.1016/s0223-5234(03)00061-8

    Article  CAS  Google Scholar 

  • Schmidt MA, Qian XH (2013) A mild synthesis of 1,2,4 triazolo 4,3-a pyridines. Tetrahedron Lett 54:5721–5726. doi:10.1016/j.tetlet.2013.08.024

    Article  CAS  Google Scholar 

  • Shang J, Sun RF, Li YQ, Huang RQ, Bi FC, Wang QM (2010) Synthesis and Insecticidal Evaluation of N-tert-Butyl-N’-thio1-(6-chloro-3-pyridylmethyl)-2-nitroiminoimidazolidine-N,N’-diacylhydrazines. J Agric Food Chem 58:1834–1837. doi:10.1021/jf903642s

    Article  CAS  Google Scholar 

  • Shen ZH, Shi YX, Yang MY, Sun ZH, Weng JQ, Tan CX, Liu XH, Li BJ, Zhao WG (2016) Synthesis, crystal structure, DFT studies and biological activity of a novel schiff base containing triazolo 4,3-a pyridine moiety. Chin J Struct Chem 35:457–464. doi:10.14102/j.cnki.0254-5861.2011-0913

    CAS  Google Scholar 

  • Tresadern G, Cid JM, Trabanco AA (2014) QSAR design of triazolopyridine mGlu2 receptor positive allosteric modulators. J Mol Graph Model 53:82–91. doi:10.1016/j.jmgm.2014.07.006

    Article  CAS  Google Scholar 

  • Vadagaonkar KS, Murugan K, Chaskar AC, Bhate PM (2014) A facile and practical one-pot synthesis of 1,2,4–triazolo[4,3-a]pyridines. Rsc Advances 4:34056–34064. doi:10.1039/c4ra04961f

    Article  CAS  Google Scholar 

  • Wang Q, Zhai ZW, Sun ZH, Liu XH, Tan CX, Weng JQ (2016) Synthesis, crystal structure and antifungal activity of 8-chloro-3-((4-chlorobenzyl)thio)-1,2,4-triazolo[4,3-a]pyridine. Chin J Struct Chem 35:651–655. doi:10.14102/j.cnki.0254-5861.2011-1022

    Article  Google Scholar 

  • Wu J, Song BA, Hu DY, Yue M, Yang S (2012a) Design, synthesis and insecticidal activities of novel pyrazole amides containing hydrazone substructures. Pest Manag Sci 68:801–810. doi:10.1002/ps.2329

    Article  CAS  Google Scholar 

  • Wu J, Wang J, Hu D, He M, Jin L, Song B (2012b) Synthesis and antifungal activity of novel pyrazolecarboxamide derivatives containing a hydrazone moiety. Chem Cent J 6:51. doi:10.1186/1752-153x-6-51

    CAS  Google Scholar 

  • Wu J, Bai S, Yue M, Luo LJ, Shi QC, Ma J, Du XL, Kang SH, Hu D, Yang S (2014) Synthesis and insecticidal activity of 6,8-dichloro-quinazoline derivatives containing a sulfide substructure. Chem Pap 68:969–975. doi:10.2478/s11696-014-0540-z

    CAS  Google Scholar 

  • Xu W, Yang S, Bhadury P, He J, He M, Gao L, Hu D, Song B (2011) Synthesis and bioactivity of novel sulfone derivatives containing 2,4-dichlorophenyl substituted 1,3,4-oxadiazole/thiadiazole moiety as chitinase inhibitors. Pestic Biochem Phys 101:6–15. doi:10.1016/j.pestbp.2011.05.006

    Article  CAS  Google Scholar 

  • Yang MY, Zhai ZW, Sun ZH, Yu SJ, Liu XH, Weng JQ, Tan CX, Zhao WG (2015) A facile one-pot synthesis of novel 1,2,4-triazolo[4,3-a]pyridine derivatives containing the trifluoromethyl moiety using microwave irradiation. J Chem Res 2015:521–523. doi:10.3184/174751915x14400874295745

    Article  Google Scholar 

  • Zhai ZW, Shi YX, Yang MY, Zhao W, Sun ZH, Weng JQ, Tan CX, Liu XH, Li BJ, Zhang YG (2016) Microwave assisted synthesis and antifungal activity of some novel thioethers containing 1,2,4-triazolo[4,3-a]pyridine moiety. Lett Drug Des Discov 13:521–525. doi:10.2174/1570180812666150918193308

    Article  CAS  Google Scholar 

  • Zhang LJ, Yang MY, Hu BZ, Sun ZH, Liu XH, Weng JQ, Tan CX (2015) Microwave-assisted synthesis of novel 8-chloro-[1,2,4]triazolo[4,3-a]pyridinederivatives. Turk J Chem 39:867–873. doi:10.3906/kim-1408-78

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was supported by the National Natural Science Foundation of China (21562012, 21302025, 21162004), the Special Foundation of S&T for Outstanding Young Talents in Guizhou (No. 2015-15), and the Introduction of Talent Research Projects of Guizhou University (No. J[2014]2056).

Author information

Authors and Affiliations

  1. State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Research and Development Center for Fine Chemicals, Guizhou University, Huaxi District, Guiyang, 550025, People’s Republic of China

    Fang-Zhou Xu, Li-Wei Liu, Yan-Yan Wang, Jian Wu, Song Yang & Wei Xue

  2. College of Life Science, Zaozhuang University, Zaozhuang, 277100, People’s Republic of China

    Jia-Hui Shao

  3. School of Chemical Engineering, Guizhou Institute of Technology, Yunyan District, Guiyang, 550001, People’s Republic of China

    Yun-Ying Zhu

  4. Institute for the Control of Agrochemicals, Ministry of Agriculture, Beijing, 100125, People’s Republic of China

    Yong-Hui Zhao & Wei-Li Shan

Authors
  1. Fang-Zhou Xu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jia-Hui Shao
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yun-Ying Zhu
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Li-Wei Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Yong-Hui Zhao
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Wei-Li Shan
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Yan-Yan Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Jian Wu
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Song Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

  10. Wei Xue
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Jian Wu or Wei Xue.

Electronic supplementary material

Below is the link to the electronic supplementary material.

11696_2016_6_MOESM1_ESM.doc

Supplementary material 1. The copies of 1H NMR and 13C NMR spectrograms of the title compounds associated with this article can be found in the online version of this paper (DOI: 10.1007/s11696-016-0006-6). (DOC 2144 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Xu, FZ., Shao, JH., Zhu, YY. et al. Synthesis, antifungal and insecticidal activity of novel [1,2,4]triazolo[4,3-a]pyridine derivatives containing a sulfide substructure. Chem. Pap. 71, 729–739 (2017). https://doi.org/10.1007/s11696-016-0006-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11696-016-0006-6

Keywords

Search

Navigation