journal article·2025-07-15Open access

Antifungal Activity of Quaternary Pyridinium Salts Against Fusarium culmorum in Wheat Seedlings

Tamara Siber, Elena Petrović, Jasenka Ćosić, Valentina Bušić, Dajana Gašo-Sokač, Karolina Vrandečić

Applied Sciences· Volume 15· Issue 14

Abstract

Wheat (Triticum aestivum L.) is a major cereal crop globally, but its production is increasingly threatened by fungal pathogens, particularly Fusarium culmorum (Wm. G. Sm.) Sacc., which causes seedling blight and root rot, leading to yield losses and mycotoxin contamination. Conventional control strategies, such as crop rotation and the use of fungicides, are often inadequate and contribute to the development of resistance, particularly with the overuse of similar modes of action. This study investigated quaternary pyridinium salts—nicotinamide and isonicotinamide derivatives—as potential sustainable antifungal agents. In vivo tests involved treating sterilized wheat seeds grown in sterile sand that had been inoculated with F. culmorum, using compounds previously confirmed to be active in vitro. Disease index, shoot and root length, and fresh and dry biomass were measured. Among the tested compounds, nicotinamide derivatives (2) and (3) showed the lowest disease index (0.9) at a concentration of 10 µg/mL. Most compounds promoted plant and root growth. Isonicotinamide derivatives (6) and (7) at 100 µg/mL increased root dry weight, while compound (6) at 10 µg/mL resulted in the most significant increase in plant length. These findings highlight the dual antifungal and growth-promoting potential of certain eco-friendly derivatives for managing F. culmorum and supporting wheat seedling development.
Source: crossref · Quality: baseline

Research context

OpenAlex topics: Mycotoxins in Agriculture and Food · Plant-Microbe Interactions and Immunity · Plant Pathogens and Fungal Diseases

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

Affiliations

Department of Phytomedicine, Faculty of Agrobiotechnical Sciences Osijek, University of Josip Juraj Strossmayer in Osijek, Vladimira Preloga 1, HR-31000 Osijek, Croatia

Department of Agriculture and Nutrition, Institute of Agriculture and Tourism, Karla Huguesa 8, HR-52440 Porec, Croatia

Department of Applied Chemistry and Ecology, Faculty of Food Technology Osijek, University of Josip Juraj Strossmayer in Osijek, Franje Kuhača 18, HR-31000 Osijek, Croatia

References (67)

Show source-provided references
1. Fusarium wilts: An overview
2. Determination of fusarium crown rot resistance in wheat to Fusarium culmorum and Fusarium pseudogramineaum using real time PCR10.1016/j.cropro.2020.105204 ↗
3. Trichothecenes and aggressiveness of Fusarium graminearum causing seedling blight and root rot in cereals10.1111/j.1365-3059.2006.01339.x ↗
4. Population genetics of three important head blight pathogens Fusarium graminearum, F. pseudograminearum and F. culmorum10.1111/j.1439-0434.2007.01394.x ↗
5. Monitoring Fusarium crown rot populations in spring wheat residues using quantitative real-time polymerase chain reaction10.1094/PHYTO-100-1-0049 ↗
6. Systematics of key phytopathogenic Fusarium species: Current status and future challenges10.1007/s10327-014-0509-3 ↗
7. FAO—Food and Agriculture Organization of United Nations (2024, November 25). Crops and Livestock Products. Available online: https://www.fao.org/faostat.
8. Fusarium vrste s različitih domaćina i njihova patogenost za klijance pšenice
9. Fusarium culmorum: Causal agent of foot and root rot and head blight on wheat10.1111/mpp.12011 ↗
10. Fusarium species and chemotypes associated with fusarium head blight and fusarium root rot on wheat in Sardinia10.1111/ppa.12337 ↗
11. Resolving Fusarium: Current status of the genus10.1146/annurev-phyto-082718-100204 ↗
12. Deoxynivalenol: Mechanisms of action, human exposure, and toxicological relevance10.1007/s00204-010-0579-8 ↗
13. Kamle, M., Mahato, D.K., Devi, S., Lee, K.E., Kang, S.G., and Kumar, P. (2019). Fumonisins: Impact on agriculture, food, and human health and their management strategies. Toxins, 11.10.3390/toxins11060328 ↗
14. Desjardins, A.E. (2006). Fusarium mycotoxins: Chemistry, Genetics, and Biology, APS Press.
15. The ability to detoxify the mycotoxin deoxynivalenol colocalizes with a major quantitative trait locus for Fusarium head blight resistance in wheat10.1094/MPMI-18-1318 ↗
16. Retrotransposon and gene activation in wheat in response to mycotoxigenic and non-mycotoxigenic-associated Fusarium stress10.1007/s00122-006-0490-0 ↗
17. Diamond, M., Reape, T.J., Rocha, O., Doyle, S.M., Kacprzyk, J., Doohan, F.M., and McCabe, P.F. (2013). The Fusarium mycotoxin deoxynivalenol can inhibit plant apoptosis-like programmed cell death. PLoS ONE, 8.10.1371/journal.pone.0069542 ↗
18. Light influences how the fungal toxin deoxynivalenol affects plant cell death and defense responses10.3390/toxins6020679 ↗
19. Perincherry, L., Lalak-Kańczugowska, J., and Stępień, Ł. (2019). Fusarium-produced mycotoxins in plant-pathogen interactions. Toxins, 11.10.3390/toxins11110664 ↗
20. Fusarium head blight of wheat: Pathogenesis and control strategies10.1016/j.cropro.2016.10.002 ↗
21. Rojas, E.C., Jørgensen, H.J., Jensen, B., and Collinge, D.B. (2018). Fusarium diseases: Biology and management Perspectives. Integrated Disease Management of Wheat and Barley, Burleigh Dodds Science Publishing.10.19103/AS.2018.0039.02 ↗
22. Islam, T., Tamanna, N.T., Matin, M.N., Barai, H.R., and Haque, M.A. (2024). Resistance mechanisms of plant pathogenic fungi to fungicide, environmental impacts of fungicides, and sustainable solutions. Plants, 13.10.3390/plants13192737 ↗
23. Gikas, G.D., Parlakidis, P., Mavropoulos, T., and Vryzas, Z. (2022). Particularities of fungicides and factors affecting their fate and removal efficacy: A review. Sustainability, 14.10.3390/su14074056 ↗
24. Fungicides: An overlooked pesticide class?10.1021/acs.est.8b04392 ↗
25. Microwave-assisted quaternization of various pyridine derivatives and their antibacterial activity
26. New 4-thiazolidinones of nicotinic acid with 2-amino-6-methylbenzothiazole and their biological activity10.3797/scipharm.1009-15 ↗
27. Synthesis of some new series of Mannich base derivatives and their antimicrobial activity
28. Synthesis and evaluation of novel analogues of vitamin B6 as reactivators of tabun and paraoxon inhibited acetylcholinesterase10.1016/j.cbi.2010.02.004 ↗
29. Syntheses and characterization of N-(indolyl) pyridinium salts and of their ylides10.5560/znb.2014-3324 ↗
30. Potent 3-hydroxy-2-pyridine aldoxime reactivators of organophosphate-inhibited cholinesterases with predicted blood–brain barrier penetration10.1002/chem.201801394 ↗
31. Pyridinium-2-carbaldoximes with quinolinium carboxamide moiety are simultaneous reactivators of acetylcholinesterase and butyrylcholinesterase inhibited by nerve agent surrogates10.1080/14756366.2020.1869954 ↗
32. Ultrasound and deep eutectic solvent (DES): A novel blend of techniques for rapid and energy efficient synthesis of oxazoles10.1016/j.ultsonch.2012.06.003 ↗
33. Deep eutectic solvents: The organic reaction medium of the century10.1002/ejoc.201501197 ↗
34. Deep eutectic solvents (DESs) as eco-friendly and sustainable solvent/catalyst systems in organic transformations10.1016/j.molliq.2015.12.015 ↗
35. Green and sustainable solvents of the future: Deep eutectic solvents10.1016/j.molliq.2023.121676 ↗
36. Bénit, P., Goncalves, J., El Khoury, R., Rak, M., Favier, J., Gimenez-Roqueplo, A.P., and Rustin, P. (2022). Succinate dehydrogenase, succinate, and superoxides: A genetic, epigenetic, metabolic, environmental explosive crossroad. Biomedicines, 10.10.20944/preprints202206.0421.v1 ↗
37. Synthesis and antifungal activities of novel nicotinamide derivatives containing 1, 3, 4-oxadiazole10.1186/1752-153X-7-64 ↗
38. Bouillaud, F. (2023). Inhibition of succinate dehydrogenase by pesticides (SDHIs) and energy metabolism. Int. J. Mol. Sci., 24.10.3390/ijms24044045 ↗
39. A rapid microwave induced synthesis of isonicotinamide derivatives and their antifungal activity10.5562/cca3527 ↗
40. Eco-friendly quaternization of nicotinamide and 2-bromoacetophenones in deep eutectic solvents. Antifungal activity of the products10.1007/s10311-020-00973-3 ↗
41. A green microwave-assisted synthesis of new pyridazinium-based ionic liquids as an environmentally friendly alternative10.4236/gsc.2011.13012 ↗
42. Tăbăcaru, A., Dediu Botezatu, A.V., Horincar, G., Furdui, B., and Dinică, R.M. (2019). Green accelerated synthesis, antimicrobial activity and seed germination test of quaternary ammonium salts of 1, 2-bis (4-pyridyl) ethane. Molecules, 24.10.3390/molecules24132424 ↗
43. Efficient microwave-assisted synthesis of 1-hexylpyridin-1-ium bromide: Anion exchange to acetate and fundamentals tools to probe its interaction with RuCl310.1016/j.molliq.2024.124080 ↗
44. Siber, T., Bušić, V., Zobundžija, D., Roca, S., Vikić-Topić, D., Vrandečić, K., and Gašo-Sokač, D. (2019). An improved method for the quaternization of nicotinamide and antifungal activities of its derivatives. Molecules, 24.10.3390/molecules24061001 ↗
45. Nelson, P.E., Toussoun, T.A., and Marasas, W.F.O. (1983). Fusarium Species: An Illustrated Manual for Identification, Pennsylvania State University Press.
46. Leslie, J.F., and Summerell, B.A. (2008). The Fusarium Laboratory Manual, John Wiley & Sons.
47. Lević, J. (2008). Vrste Roda Fusarium u Oblasti Poljoprivrede, Veterinarske i Humane Medicine, Institut za kukuruz “Zemun Polje”.
48. Genus-specific primers for study of Fusarium communities in field samples10.1128/AEM.02748-15 ↗
49. Investigations of the rosette disease of wheat and its control
50. Fusarium wilt disease of strawberry caused by Fusarium oxysporum f. sp. Fragariae in Iraq and its control
51. Kumar, V., and Chandel, S. (2025, April 12). Effect of Epidemiological Factors on Percent Disease Index of Rose Powdery Mildew Caused by Podosphaera pannosa (Wallr.) de Bary. Available online: https://www.researchgate.net/publication/327866159.
52. Comparative analysis of artificial inoculation methods with Fusarium spp. on winter wheat varieties10.1111/j.1439-0434.1978.tb03632.x ↗
53. Common tasks in microscopic and ultrastructural image analysis using ImageJ10.1080/01913120701719189 ↗
54. Effectiveness of fungicide seed treatment in the control of soybean seedling damping off caused by Rhizoctonia solani under greenhouse conditions10.1590/0100-5405/266033 ↗
55. Wang, W., Liu, X.J., Lin, G.T., Wu, J.P., Xu, G., and Xu, D. (2022). Novel N-(1H-pyrazol-5-yl) nicotinamide derivatives: Design, synthesis and antifungal activity. Chem. Biodivers., 19.10.1002/cbdv.202101032 ↗
56. Synthesis and antifungal activity of novel tetrahydrogeranyl quaternary ammonium salts
57. Sidiq, Y., Nakano, M., Mori, Y., Yaeno, T., Kimura, M., and Nishiuchi, T. (2021). Nicotinamide effectively suppresses fusarium head blight in wheat plants. Int. J. Mol. Sci., 22.10.3390/ijms22062968 ↗
58. Evaluation of the efficacy of salicylic acid and nicotinic acid to control collar rot and root rot caused by Sclerotium rolfsii and enhance the productivity of fenugreek (Trigonella foenum-groecum L.) in Egypt
59. Ueda, K., Nakajima, Y., Inoue, H., Kobayashi, K., Nishiuchi, T., Kimura, M., and Yaeno, T. (2021). Nicotinamide mononucleotide potentiates resistance to biotrophic invasion of fungal pathogens in barley. Int. J. Mol. Sci., 22.10.3390/ijms22052696 ↗
60. Smolik, B., and Sędzik-Wójcikowska, M. (2024). Examining nicotinamide application methods in alleviating lead-induced stress in Spring Barley. Agronomy, 14.10.3390/agronomy14061314 ↗
61. Plant defence responses in isonicotinamide-treated tobacco cells. Evidence supporting a role for nicotinamide related metabolites as stress mediators in plant defense metabolism10.1016/S0176-1617(00)80268-0 ↗
62. Yan, S., Weng, B., Jing, L., and Bi, W. (2023). Effects of drought stress on water content and biomass distribution in summer maize (Zea mays L.). Front. Plant Sci., 14.10.3389/fpls.2023.1118131 ↗
63. Increasing sunflower salt tolerance using nicotinamide and α--tocopherol
64. Hormesis in plants: Its common occurrence across stresses10.1016/j.cotox.2022.02.006 ↗
65. Hormesis and plant biology10.1016/j.envpol.2008.07.028 ↗
66. Jodynis-Liebert, J., and Kujawska, M. (2020). Biphasic dose-response induced by phytochemicals: Experimental evidence. J. Clin. Med., 9.10.3390/jcm9030718 ↗
67. Zandona, A., Lihtar, G., Maraković, N., Miš, K., Bušić, V., Gašo-Sokač, D., and Katalinić, M. (2020). Vitamin B3-based biologically active compounds as inhibitors of human cholinesterases. Int. J. Mol. Sci., 21.10.3390/ijms21218088 ↗