Cationic gemini compounds with antifungal activity and wood preservation potentiality

Marcelo Cesar Murguia; Laura Marcela Machuca; Maria Emilia Fernandez

Journal of Industrial and Engineering Chemistry, Vol.72, 170-177, April, 2019

DOI10.1016/j.jiec.2018.12.016 Export Citation

Cationic gemini compounds with antifungal activity and wood preservation potentiality

Marcelo Cesar Murguia^{1, 2}, Laura Marcela Machuca^{3, 4}, and Maria Emilia Fernandez^{5, 3, †}

¹Laboratorio de Quimica Aplicada (LAQUIMAP), Facultad de Bioquimica y Ciencias Biologicas, Universidad Nacional del Litoral (UNL), CC 242, Ciudad Universitaria, 3000 Santa Fe, Argentina
²Grupo Medio Ambiente, Instituto de Desarrollo Tecnicas, Godoy Cruz 2290, C1425FQB Buenos Aires, Argentina
³Consejo Nacional de Investigaciones Cientificas y Tecnicas (CONICET), Godoy Cruz 2290, C1425FQB Buenos Aires, Argentina
⁴Instituto de Investigaciones Cientificas (IDIC), Facultad de Ingenieria y Tecnologia, Universidad de la Cuenca del Plata (UCP), Corrientes 57, 3450 Goya, nes Científicas (IDIC), Facultad de Ingeniería y Tecnología, Universidad de la Cuenca del Plata (UCP), Corrientes 57, 3450 Goya,, Argentina
⁵Grupo Medio Ambiente, Instituto de Desarrollo Tecnologico para la Industria Quimica (INTEC-UNL-CONICET), Guemes 3450, 3000 Santa Fe, Argentina

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Three gemini compounds were synthesized and characterized in the search of an alternative eco-friendly wood preservative. Synthesis was carried out from N,N-dimethylamines and 2-O-acetyl-1,3- dichloropropane as linker molecule. All the synthesized molecules were adequately purified and characterized by TLC, GC, FT-IR and NMR. Their tensioactive properties were determined. All three efficiently lowered the surface tension in aqueous solutions with critical micelle concentrations ranging from 0.53 to 1.34 mM. Their antifungal activities were evaluated from a broth dilution test against four yeasts and two filamentous fungi and were compared to commercially available references: Fluconazole and TCMTB (2-thiocyanomethylthiobenzothiazole). All gemini compounds displayed good antifungal activity; particularly, the gemini derived from N,N-dimethyldodecylamine, with even better performance than Fluconazole against Saccharomyces cerevisiae, Aspergillus niger and Alternaria sp., and than TCMTB against the last one. The environmental impact of the gemini compound that showed the highest antifungal activity was analyzed through ecotoxicity tests, using Chlorella vulgaris and Daphnia magna as model organisms. It was several orders of magnitude less toxic than TCMTB. Finally, wood preservation efficacy studies were carried out on pine (Pinus ponderosa) samples. Results demonstrated accomplished resistance against brown rot fungi, comparable to a widespread commercial hydrosoluble preservative.

Keywords:Gemini compounds;Antifungal;Ecotoxicity tests;Wood preservative;Wood-decay fungi

[References]

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[2] Hassan EB, El-Giar EM, Steele P, Int. Biodeterior. Biodegr., 110, 121 (2016)

[3] Mohajerani A, Vajna J, Ellcock R, J. Clean Prod., 179, 292 (2018)

[4] Barnes HM, Reference Module in Materials Science and Materials Engineering, Elsevier, 2016, doi:http://dx.doi.org/10.1016/B978-0-12-803581-8.02222-0 p. 7.

[5] Karunasekera H, Terziev N, Daniel G, Int. Biodeterior. Biodegrad., 117, 105 (2017)

[6] Murguia MC, Vaillard VA, Sanchez VG, Di Conza J, Grau RJ, J. Oleo Sci., 57, 301 (2008)

[7] Tehrani-Bagha AR, Colloids Surf. A: Physicochem. Eng. Asp., 508, 79 (2016)

[8] Garcia MT, Kaczerewska O, Ribosa I, Brycki B, Materna P, Drgas M, Chemosphere, 154, 155 (2016)

[9] Tatsumi T, Imai Y, Kawaguchi K, Miyano N, Ikeda I, J. Oleo Sci., 63, 137 (2014)

[10] Massi L, Guittard F, Geribaldi S, Levy R, Duccini Y, Int. J. Antimicrob. Agents, 21, 20 (2003)

[11] Obłak E, Piecuch A, Krasowsk A, Łuczynskic J, Microbiol. Res., 168, 630 (2013)

[12] Caillier L, de Givenchy ET, Levy R, Vandenberghe Y, Geribaldi S, Guittard F, J. Colloid Interface Sci., 332(1), 201 (2009)

[13] Sharma R, Kamal A, Abdinejad M, Mahajan RK, Kraatz HB, Adv. Colloid Interface, 248, 35 (2017)

[14] Mondal MH, Malik S, Roy A, Sahab R, Saha B, RSC Adv., 5, 92707 (2015)

[15] Yang J, Yun L, Zhao G, Zhang F, Chen Y, Wang C, Colloids Surf. A: Physicochem. Eng. Asp., 539, 101 (2018)

[16] Murguia MC, Muller DM, Argarana MF, Lura MC, Biocidal Compound, Its Production Process and Wood Preservative Composition. Bulletin, 822 Argentina, (2013).

[17] Vogel AI, Furniss BS, Hannaford AJ, Smith PWG, Tatachell AR, Vogel’s Textbook of Practical Organic Chemistry, fifth ed., Prentice Hall, New Jersey, 1996.

[18] Szlavik Z, Tarkanyi G, Gomory A, Tarczay G, Rabai J, J. Fluor. Chem., 108, 7 (2001)

[19] Kaplanek R, Paleta O, J. Fluor. Chem., 128(7), 789 (2007)

[20] Murguia MC, Machuca LM, Lura MC, Cabrera MI, Grau RJ, J. Surfactants Deterg., 11, 223 (2008)

[21] NCCLS (National Committee for Clinical Laboratory Standards) M27-A2, Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts, NCCLS, Wayne (PA), 2002.

[22] NCCLS (National Committee for Clinical Laboratory Standards) M38-A, Reference Method for Broth Dilution Antifungal Susceptibility Testing of Filamentous Fungi, NCCLS, Wayne (PA), 2002.

[23] Khadiran T, Salamah S, Rozita A, Salmiah U, Nasir MAM, Wood Sci. Technol., 46, 1021 (2012)

[24] Fernandez-Alba AR, Hernando AR, Piedra L, Chisti Y, Anal. Chim. Acta, 456, 303 (2002)

[25] Ronco A, Baez MCD, Ensayos toxicologicos y metodos de evaluacion de calidad de aguas. Estandarizacion, intercalibracion, resultados y aplicaciones, IMTA, Mexico, p.141 2004.

[26] Diaz-Baez MC, Bulus-Rossini GD, Pica-Granados Y, Ensayos Toxicologicos y Metodos de Evaluacion de Calidad de Aguas. Estandarizacion, Intercalibracion, Resultados y Aplicaciones, IMTA, Mexico, p.99 2004.

[27] Gomez E, Palacio JA, Aguirre NJ, Actual Biol., 23, 41 (2001)

[28] IRAM (Argentine Institute of Materials Rationalization) standard 9544, Method for Determination of the Bulk Density, 10pp (1985).

[29] IRAM (Argentine Institute of Materials Rationalization) standard 9518, Toxicity, Permanence and Efficiency of Wood Preservers, 12pp. (1962).

[30] Morais DS, Guedes RM, Lopes MA, Materials, 9(498), 1 (2016)

[31] Kaczerewska O, Brycki B, Ribosa I, Comelles F, Garcia MT, J. Ind. Eng. Chem., 59, 141 (2018)

[32] Tavano L, Infante MR, Abo Riy M, Pinazo A, Vinardell MP, Mitjans M, Manresag MA, Perez L, Soft Matter, 9, 306 (2013)

[33] Li H, Yu C, Chen R, Li J, Li J, Colloids Surf. A: Physicochem. Eng. Asp., 395, 116 (2012)

[34] Massi L, Guittard F, Levy R, Geribaldi S, Eur. J. Med. Chem., 44, 1615 (2009)

[35] Matan N, Matan N, Int. Biodeterior. Biodegr., 62, 75 (2008)

[36] Machuca LM, Reno U, Plem SC, Gagneten AM, Murguia MC, Adv. Chem. Eng. Sci., 5, 215 (2015)

[37] Boudreau TM, Sibley PK, Mabury SA, Muir DGC, Solomon KR, Arch. Environ. Contam. Toxicol., 44, 307 (2003)

[38] ASTM D-2017.1981, Standard Method of Accelerated Laboratory Tests of Natural Decay Resistance of Woods, ASTM International, 1986.

[39] Ringman R, Pilgard A, Richter K, Int. Biodeterior. Biodegr., 86, 86 (2014)