1-Aryl-2-Nitroethenes as Antimicrobial Additives for Lubricating Materials
Abstract
This study presents the first systematic evaluation of 1-aryl-2-nitroethenes as antimicrobial additives in M-11 lubricating oils. A series of nine substituted derivatives (R = H, p-CH₃, p-OCH₃, o/p-F, o/p-Cl, o/p-OH) were synthesized via Henry condensation and characterized by FT-IR, ¹H NMR, and melting point analysis. Antimicrobial efficacy was assessed against Pseudomonas aeruginosa ATCC 27853, Bacillus subtilis ATCC 6633, Aspergillus niger ATCC 16404, and Penicillium chrysogenum ATCC 10106 using GOST 9.052-75 and GOST 9.082-77 protocols (n = 3, ANOVA, p < 0.05). Halogen-substituted derivatives (p-F, o-Cl) demonstrated superior activity (MIC 0.01–0.05% for bacteria; 0.01–0.025% for fungi), outperforming the commercial biocide 1,3-bis(2-hydroxyethyl)-1,3-diazacyclobutane (MIC 0.25–0.5%). Notably, 0.05% additive concentrations preserved the physicochemical properties of M-11 oil over 450 days, whereas untreated oil exhibited significant degradation. These results establish 1-aryl-2-nitroethenes as promising, cost-effective antimicrobial additives for industrial lubricants.
Keywords
References
- 1. de Albuquerque PCC, de Andrade Ávila RN, Barros Zárante PH, Sodré JR. Lubricating oil influence on exhaust hydrocarbon emissions from a gasoline fueled engine. Tribol Int. 2011 Nov 1;44(12):1796–9. Available from:
. - 2. Wu Y, van der Heide E, He Z. Effect of sulfur on the hydrolytic stability and tribological properties of N-containing borate ester. Wear. 2022 Sep 15;504–505:204433. Available from:
. - 3. Farzaliev VM, Babaeva GB, Abbasova MT, Nabiev OG, Soltanova ZK, Kerimova YM. Derivatives of N-alkyl(aryl)-1,2(1,3)-diazacycloalkanes. Antimicrobial properties. Chem Technol Fuels Oils. 2009 Mar 16;45(2):98–102. Available from:
. - 4. Mertoglu C. The synthesis and characterization of thioglycolic acid derivatives and their use in the preparation of ZnS nanoparticles. [Ankara]: Middle East Technical University; 2011. Available from:
. - 5. Vauzour D, Rodriguez-Mateos A, Corona G, Oruna-Concha MJ, Spencer JPE. Polyphenols and human health: Prevention of disease and mechanisms of action. Nutrients. 2010 Nov 8;2(11):1106–31. Available from:
. - 6. Ding M, Mo Y, Zhang H, Liu Q. Synergistic effect of acrylate of dialkyl dithiophosphoric acid combined with molybdenum dialkyl dithiocarbamate as additives in gear oil. Lubricants. 2024 May 9;12(5):165. Available from:
. - 7. Burton GW, Ingold KU. Autoxidation of biological molecules. 1. Antioxidant activity of vitamin E and related chain-breaking phenolic antioxidants in vitro. J Am Chem Soc. 1981 Oct 1;103(21):6472–7. Available from:
. - 8. Howard JA, Bennett JE. The self-reaction of sec-alkylperoxy radicals: A kinetic electron spin resonance study. Can J Chem. 1972 Jul 15;50(14):2374–7. Available from:
.
Details
Primary Language
English
Subjects
Physical Organic Chemistry
Journal Section
Research Article
Authors
Aida Yusifova
0000-0002-8656-9307
Azerbaijan
Mansura Huseynova
*
0000-0002-1534-6819
Azerbaijan
Tarana Dadashova
This is me
0000-0002-0068-302X
Azerbaijan
Gulshan Yusifzadeh
0000-0002-0957-1913
Azerbaijan
Rayyat Ismayilov
This is me
0009-0004-7753-6468
Azerbaijan
Sabina Ismayilova
This is me
0000-0002-3957-7996
Azerbaijan
Chinara Mammadli
This is me
0000-0001-7920-7618
Azerbaijan
Malakhat Abbasova
This is me
0000-0002-0582-4653
Azerbaijan
Barbaros Akkurt
0000-0003-4066-3004
Türkiye
Bahattin Yalcin
0000-0003-4448-1101
Türkiye
Publication Date
August 11, 2026
Submission Date
May 15, 2026
Acceptance Date
July 5, 2026
Published in Issue
Year 2026 Volume: 2026 Number: 2
