Skip to main content
SpringerLink
Log in

Synthesis and in vivo nematocidal evaluation of novel 3-(trifluoromethyl)-1H-pyrazole-4-carboxamide derivatives

  • Research Article
  • Published:
Frontiers of Chemical Science and Engineering Aims and scope Submit manuscript

Abstract

Pyrazole carboxamide derivatives represent an important class of fungicides in agrochemicals. To find more novel structural pyrazole carboxamides, a novel series of 3-(trifluoromethyl)-1H-pyrazole-4-carboxamide compounds were prepared from ethyl 4,4,4-trifluoroacetoacetate and triethyl orthoformate as starting materials. All the products were characterized by Fourier transform infrared spectroscopy, 1H nuclear magnetic resonance (NMR), 13C NMR, 19F NMR and mass spectrography. The bioassay results showed these fluorine-containing pyrazole carboxamides have a weak fungicidal activity but some of them exhibit a good nematocidal activity against M. incognita.

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

Similar content being viewed by others

References

  1. Khatri H R, Nguyen H, Dunaway J K, Zhu J. Fluoroalcoholmediated reductive iodonio-Claisen rearrangement: Synthesis of complex ortho-substituted-allyl iodoarenes. Frontiers of Chemical Science and Engineering, 2015, 9(3): 359–368, 368

    Article  CAS  Google Scholar 

  2. Liu X H, Zhai Z W, Xu X Y, Yang M Y, Sun Z H,Weng J Q, Tan C X, Chen J. Facile and efficient synthesis and herbicidal activity determination of novel 1,2,4-triazolo[4,3-a]pyridin-3(2H)-one derivatives via microwave irradiation. Bioorganic & Medicinal Chemistry Letters, 2015, 25(23): 5524–5528

    Article  CAS  Google Scholar 

  3. Emmadi N R, Bingi C, Kotapalli S S, Ummanni R, Nanubolu J B, Atmakur K. Synthesis and evaluation of novel fluorinated pyrazolo-1,2,3-triazole hybrids as antimycobacterial agents. Bioorganic & Medicinal Chemistry Letters, 2015, 25(15): 2918–2922

    Article  CAS  Google Scholar 

  4. Giornal F, Landelle G, Lui N, Vors J P, Pazenok S, Leroux F R. A new synthesis and process development of bis(fluoroalkyl)pyrazoles as novel agrophores. Organic Process Research & Development, 2014, 18(8): 1002–1009

    Article  CAS  Google Scholar 

  5. Jeschke P. The unique role of halogen substituents in the design of modern agrochemicals. Pest Management Science, 2010, 66(1): 10–27

    Article  CAS  Google Scholar 

  6. Francke R, Reingruber R, Schollmeyer D, Waldvogel S R. Highly fluorinated 2,2'-biphenols and related compounds: Relationship between substitution pattern and herbicidal activity. Journal of Agricultural and Food Chemistry, 2013, 61(20): 4709–4714

    Article  CAS  Google Scholar 

  7. Prakash G K S, Vaghoo H, Venkat A, Panja C, Chacko S, Mathew T, Olah G A. Gallium (III) triflate-catalyzed synthesis of heterocycles: Quinoxalines, 1,5-benzodiazepines and their fluorinated derivatives. Future Medicinal Chemistry, 2009, 1(5): 909–920

    Article  CAS  Google Scholar 

  8. Bonacorso H G, Cavinatto S, Moraes M C, Pittaluga E P, Peroza L R, Venturini T, Alves S H, Stefanello S T, Soares F A A, Martins M A P. Synthesis, structure elucidation, antioxidant and antimicrobial activity of novel 2-(5-trifluoromethyl-1H-pyrazol-1-yl)-5-(5-trihalomethyl-1H-pyrazol-1-yl-1carbonyl) pyridines. Journal of the Brazilian Chemical Society, 2015, 26: 2346–2361

    CAS  Google Scholar 

  9. Holland J P, Jones M W, Cohrs S, Schibli R, Fischer E. Fluorinated quinazolinones as potential radiotracers for imaging kinesin spindle protein expression. Bioorganic & Medicinal Chemistry, 2013, 21(2): 496–507

    Article  CAS  Google Scholar 

  10. Mustafa G. Zia-ur-Rehman M, Khan I U, Ishtiaq S, Hussain S, Arshad M N, Asiri A M. Novel 4-[5-{4-[(2-benzylidenehydrazine) carbonyl]phenyl}-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamides: Synthesis crystal structure anti-inflammatory and ulcerogenecity studies. Journal of Chemical Research, 2016, 3: 167–172

    Article  Google Scholar 

  11. Valdez-Calderón A, Gonzalez-Montiel S, Martinez-Otero D, Martinez-Torres A, Vasquez-Perez J M, Molina-Vera C, Torres-Valencia J M, Alvarado-Rodriguez J G, Cruz-Borbolla J. Synthesis structural study and biological activity of new derivatives of chrysin containing a 2-mercaptopyridyl or 5-(trifluoromethyl)-2-mercaptopyridyl fragments. Journal of Molecular Structure, 2016, 1110: 196–207

    Article  Google Scholar 

  12. Emmadi N R, Bingi C, Kotapalli S S, Ummanni R, Nanubolu J B, Atmakur K. Synthesis and evaluation of novel fluorinated pyrazolo-123-triazole hybrids as antimycobacterial agents. Bioorganic & Medicinal Chemistry Letters, 2015, 25(15): 2918–2922

    Article  CAS  Google Scholar 

  13. Karad S C, Purohit V B, Raval D K, Kalaria P N, Avalani J R, Thakor P, Thakkar V R. Green synthesis and pharmacological screening of polyhydroquinoline derivatives bearing a fluorinated 5-aryloxypyrazole nucleus. RSC Advances, 2015, 5(21): 16000–16009

    Article  CAS  Google Scholar 

  14. Ma H J, Zhang J H, Xia X D, Kang J, Li J H. Design synthesis and herbicidal evaluation of novel 4-(1H-pyrazol-1-yl)pyrimidine derivatives. Pest Management Science, 2015, 71(8): 1189–1196

    Article  CAS  Google Scholar 

  15. Zhou S, Gu Y C, Liu M, Wu C C, Zhou S, Zhao Y, Jia Z H,Wang B L, Xiong L X, Yang N, Li Z. Insecticidal activities of chiral Ntrifluoroacetyl sulfiliminesas potential ryanodine receptor modulators. Journal of Agricultural and Food Chemistry, 2014, 62(46): 11054–11061

    Article  CAS  Google Scholar 

  16. Zhu X L, Xiong L, Li H, Song X Y, Liu J J, Yang G F. Computational and experimental insight into the molecular mechanism of carboxamide inhibitors of succinate-ubquinone oxidoreductase. ChemMedChem, 2014, 9(7): 1512–1521

    Article  CAS  Google Scholar 

  17. Xiong L, Shen Y Q, Jiang L N, Zhu X L, Yang W C, Huang W, Yang G F. Succinate dehydrogenase: An ideal target for fungicide discovery. ACS Symposium Series, 2015, 1204: 175–194

    CAS  Google Scholar 

  18. Xiong L, Zhu X L, Shen Y Q, Wishwa W K W M, Li K, Yang G F. Discovery of N-benzoxazol-5-yl-pyrazole-4-carboxamides as nanomolar SQR inhibitors. European Journal of Medicinal Chemistry, 2015, 95: 424–434

    Article  CAS  Google Scholar 

  19. Xiong L, Zhu X L, Gao H W, Fu Y, Hu S Q, Jiang L N, Yang W C, Yang G F. Discovery of potent succinate-ubiquinone oxidoreductase inhibitors via pharmacophore-linked fragment virtual screening approach. Journal of Agricultural and Food Chemistry, 2016, 64(24): 4830–4837

    Article  CAS  Google Scholar 

  20. Zhai Z W, Shi Y X, Yang M Y, Zhao W, Sun Z H, Weng J Q, Tan C X, Liu X H, Li B J, Zhang Y G. Microwave assisted synthesis and antifungal activity of some novel thioethers containing 1,2,4-triazolo[4,3-a]pyridine moiety. Letters in Drug Design & Discovery, 2016, 13(6): 521–525

    Article  CAS  Google Scholar 

  21. Liu X H, Zhao W, Shen Z H, Xing J H, Xu T M, Peng W L. Synthesis, nematocidal activity and SAR study of novel difluoromethylpyrazole carboxamide derivatives containing flexible alkyl chain moieties. European Journal of Medicinal Chemistry, 2017, 125: 881–889

    Article  CAS  Google Scholar 

  22. Liu X H, Wang Q, Sun Z H, Wedge D E, Becnel J J, Estep A S, Tan C X, Weng J Q. Synthesis and insecticidal activity of novel pyrimidine derivatives containing urea pharmacophore against Aedes aegypti. Pest Management Science, 2016, doi: 101002/ps4370

    Google Scholar 

  23. Bacha P, Boströma J, Brickmannb K, van Giezenc J J J, Hovlandb R, Peterssonb A U, Rayb A, Zetterberga F. A novel series of piperazinyl-pyridine ureas as antagonists of the purinergic P2Y12 receptor. Bioorganic & Medicinal Chemistry Letters, 2011, 21(10): 2877–2881

    Article  Google Scholar 

  24. Wu Z, Hu D, Kuang J, Cai H, Wu S, Xue W. Synthesis and antifungal activity of N-(substituted pyridinyl)-1-methyl(phenyl)-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide derivatives. Molecules (Basel, Switzerland), 2012, 17(12): 14205–14218

    Article  CAS  Google Scholar 

  25. Chen Q, Liao D H, Zhang S G, Niu J F, Tang A P. Synthesis of 1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carbonyl chloride. Pesticide, 2012, 51: 569–572

    Google Scholar 

  26. Zhao W, Shen Z H, Xu T M, Peng W L, Liu X H. Synthesis, nematocidal activity and docking study of novel chiral 1-(3-chloropyridin-2-yl)-3-(difluoromethyl)-1H-pyrazole-4-carboxamide derivatives. Journal of Heterocyclic Chemistry, 2016, doi: 101002/jhet2753

    Google Scholar 

  27. Liu X H, Zhao W, Shen Z H, Xing J H, Yuan J, Yang G, Xu T M, Peng W L. Synthesis, nematocidal activity and docking study of novel chiral 1-(3-chloropyridin-2-yl)-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide derivatives. Bioorganic & Medicinal Chemistry Letters, 2016, 26(15): 3626–3628

    Article  CAS  Google Scholar 

  28. Sun M, Yang H H, Tian L, Li J Q, Zhao WG. Design, synthesis, and fungicidal activities of imino diacid analogs of valine amide fungicides. Bioorganic & Medicinal Chemistry Letters, 2015, 25(24): 5729–5731

    Article  CAS  Google Scholar 

  29. Wang Z J, Gao Y, Hou Y L, Zhang C, Yu S J, Bian Q, Li Z M, Zhao W G. Design, synthesis, and fungicidal evaluation of a series of novel 5-methyl-1H-1,2,3-trizole-4-carboxyl amide and ester analogues. European Journal of Medicinal Chemistry, 2014, 86: 87–94

    Article  CAS  Google Scholar 

  30. Li J Q, Wang Z P, Gao Y, Zhao WG. Design, synthesis and effect of the introduction of a propargyloxy group on the fungicidal activities of 1-substituted phenoxypropan-2-amino valinamide carbamate derivatives. RSC Advances, 2016, 6(85): 82131–82137

    Article  CAS  Google Scholar 

  31. Wang Z P, Kou J J, Gao Y, Du X J, Li Y H, Zhao W G. Design, synthesis and antifungal activity of carboxylic acid amide fungicides: Part 2: Substituted 1-phenyl-2-phenoxyethylamino valinamide carbamates. RSC Advances, 2015, 5(92): 75121–75128

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was supported financially by Zhejiang Provincial Science Foundation of China (No. LY16C140007) and Research Institute Special Program of Department of Science and Technology of Zhejiang Province (No. 2015F50030).

Author information

Authors and Affiliations

  1. College of Chemical Engineering, Zhejiang University of Technology, Hangzhou, 310014, China

    Wen Zhao & Xinghai Liu

  2. Zhejiang Base of National Southern Pesticide Research Centre, Zhejiang Research Institute of Chemical Industry, Hangzhou, 310023, China

    Jiahua Xing, Tianming Xu & Weili Peng

Authors
  1. Wen Zhao
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jiahua Xing
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Tianming Xu
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Weili Peng
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Xinghai Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Weili Peng or Xinghai Liu.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zhao, W., Xing, J., Xu, T. et al. Synthesis and in vivo nematocidal evaluation of novel 3-(trifluoromethyl)-1H-pyrazole-4-carboxamide derivatives. Front. Chem. Sci. Eng. 11, 363–368 (2017). https://doi.org/10.1007/s11705-016-1595-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11705-016-1595-x

Keywords

Search

Navigation