Allyl and Propargyl Ethers of Dihaloalkanols: Synthesis and Study of Them as Antimicrobial Additives

Gulahmad Talybov; S. Ibrahimova

doi:10.17721/fujcV13I2P24-30

Authors

Gulahmad Talybov prof.
S. Ibrahimova

DOI:

https://doi.org/10.17721/fujcV13I2P24-30

Keywords:

dimethylacetylenecarbinol, dihaloalkanol, oil additives, antimicrobial activity

Abstract

Based on the catalytic addition of dimethylacetylenecarbinol to allyl halides with the participation of N-bromosuccinimide and molecular iodine, methods for the synthesis of simple 2-methyl-3-butyn-2-ol ethers of dihaloalkanols (chlorine, bromine and iodine derivatives) have been proposed. The resulting compounds were studied as antimicrobial additives for lubricating oils and fuels. The antimicrobial effectiveness of the studied compounds was determined by the zonal diffusion method using microorganisms: Pseudomonas aeruginosa, Mycobacterium phlei, Aspergillus niger, Penicillium chrysogenum, Cladosporium resinae. It was revealed that 2-methyl-3-butyn-2-ol ethers of dihaloalkanols with two iodine atoms significantly inhibit the growth of microorganisms at low concentrations. It has been established that iodoethers are 2-4.5 times more effective than ethanol. Unsaturated ethers do not decompose and cannot be corrosive; their use for these purposes does not cause side effects.

References

Baret N, Dulcere J, Rodriguez J, Pons J, Faure R. The Cohalogenation of 1-N-Vinylpyrimidinediones: A New Approach to Nucleoside Analogs. European Journal of Organic Chemistry 2000;2000(8):1507-1516. https://doi.org/10.1002/(sici)1099-0690(200004)2000:8<1507::aid-ejoc1507>3.0.co;2-k

Luz G, Sousa B, Guedes A, Barreto C, Brasil L. Biocides Used as Additives to Biodiesels and Their Risks to the Environment and Public Health: A Review. Molecules 2018;23(10):2698. https://doi.org/10.3390/molecules23102698

Kahrilas G, Blotevogel J, Stewart P, Borch T. Biocides in Hydraulic Fracturing Fluids: A Critical Review of Their Usage, Mobility, Degradation, and Toxicity. Environmental Science & Technology 2014;49(1):16-32. https://doi.org/10.1021/es503724k

Pastor A, Gámiz B, Cruz-Yusta M, Sánchez L, Pavlovic I. Carbendazim-clay complexes for its potential use as antimicrobial additives in mortars. Building and Environment 2020;183:107214. https://doi.org/10.1016/j.buildenv.2020.107214

Lemire J, Harrison J, Turner R. Antimicrobial activity of metals: mechanisms, molecular targets and applications. Nature Reviews Microbiology 2013;11(6):371-384. https://doi.org/10.1038/nrmicro3028

Benincá T, Schmidt L, Thomé Cardoso L, Rossini Augusti P, da Silva Malheiros P. Carvacrol as a food additive: Toxicological aspects and the role of nanotechnology in enhancing its antimicrobial and antioxidant properties. Food Research International 2024;197:115256. https://doi.org/10.1016/j.foodres.2024.115256

Yeasmin R, Zhang H, Zhu J, Cadieux P. Fabrication and analysis of antimicrobial additives for powder coated surface. Progress in Organic Coatings 2019;127:308-318. https://doi.org/10.1016/j.porgcoat.2018.11.016

Dutta P, Wang B. Zeolite-supported silver as antimicrobial agents. Coordination Chemistry Reviews 2019;383:1-29. https://doi.org/10.1016/j.ccr.2018.12.014

Cui J, Shao Y, Zhang H, Zhang H, Zhu J. Development of a novel silver ions-nanosilver complementary composite as antimicrobial additive for powder coating. Chemical Engineering Journal 2021;420:127633. https://doi.org/10.1016/j.cej.2020.127633

Arunachalam S, Padma Priya N, Boopathi K, Jayabalakrishnan C, Chinnusamy V. Biocidal and catalytic efficiency of ruthenium(III) complexes with tridentate Schiff base ligands. Applied Organometallic Chemistry 2010;24(7):491-498. https://doi.org/10.1002/aoc.1647

Priya N, Arunachalam S, Manimaran A, Muthupriya D, Jayabalakrishnan C. Mononuclear Ru(III) Schiff base complexes: Synthesis, spectral, redox, catalytic and biological activity studies. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2009;72(3):670-676. https://doi.org/10.1016/j.saa.2008.10.028

Talybov G, Ezizbeyli A, Mammadbayli E, Gurbanov G. Alkoxyhalogenation of Dichlorostyrenes in Unsaturated C3-Alcohols. Russian Journal of Organic Chemistry 2020;56(1):34-37. https://doi.org/10.1134/s1070428020010066

Talybov G. Heterocyclization of Allyloxyiodination Products of Halogen-Substituted Styrenes. Russian Journal of Organic Chemistry 2021;57(6):1009-1011. https://doi.org/10.1134/s1070428021060191

Talybov G, Ezizbeyli A, Mammadbayli E, Shirinova N, Guliyeva N. Regioselective Alkoxyiodination of Allyl Ethers in Unsaturated C3-Alcohols. Russian Journal of Organic Chemistry 2020;56(3):552-554. https://doi.org/10.1134/s1070428020030318