Synthesis of Mono and Di -2,6-Dichloro-3- Methyl aniline Organophosphate esters and Characterization by FTIR Spectroscopy and Biological Activity – Acute Oral Toxicity Study.
Keywords:
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Abstract
In this study, spectroscopic characterization, and assessment of acute oral toxicity of mono and di-2, 6-dichloro-3-metylaniline organophosphate esters derived from 2,6-dichloro-3-methylaniline are the main objective. We created the Mono-2, 6-dichloro-3-methylaniline organophosphate ester and di-2, 6-dichloro-3-methylaniline organophosphate ester and acute toxicity evaluations were carried out in vivo in accordance with OECD guidelines as per graded doses viz. 5, 50, 300, and 2000 mg/kg and the structural elucidation was done by using FTIR and in a 1:1 molar ratio, the mono 2, 6-dichloro-3-methylaniline organophosphate ester was created using Auger and Dupis' method. The Mono-2,6-dichloro-3-methylaniline organophosphate ester was identified as a white, odorless solid powder that melts on 330°C and gives 75% yield, a 2:1 molar ratio of 2, 6-dichloro-3-methylaniline to phosphoric acid, the Auger and Dupis method was also used to create the Di-2, 6-dichloro-3-methylaniline organophosphate ester. The synthesized Di-2,6-dichloro-3-methylaniline organophosphate ester, was isolated as a white powder possessing a sweet and aromatic odour, with 72% yield and a melts on 336°C. The compound exhibited a solid state and uniform crystalline morphology, reflecting good thermal stability.
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3. Verma, A., &Andleep, F. Synthesis of Mono-(4-Chlorothio) Phenyl Phosphate Ester and Its Characterization from IR Absorption Spectra. Carbon, 32, 31-15.
4. Singh, M. K. (2008). Synthesis and characterisation of some phosphate esters. Oriental Journal of Chemistry, 24(2), 749.
5. Douglas, A. S., & Donald, M. W. (1971). Principles of instrumental analysis. Holt, Rinhart, Winston, New York.
6. Greaves, A. K., Letcher, R. J., Chen, D., McGoldrick, D. J., Gauthier, L. T., & Backus, S. M. (2016). Retrospective analysis of organophosphate flame retardants in herring gull eggs and relation to the aquatic food web in the Laurentian Great Lakes of North America. Environmental Research, 150, 255-263.
7. Kashimawo, A., Ouserigha, E., & Bunu, S. (2025). Antiproliferative and Acute Toxicity Assay of Hydroethanolic Extract of Smilax kraussiana as an Ethnomedicinal Plant. Asian Journal of Biology, 21(5), 5-17.
8. Chen, Y., Yang, Z., Nian, B., Yu, C., Maimaiti, D., Chai, M., ... & Xu, D. (2024). Mechanisms of neurotoxicity of organophosphate pesticides and their relation to neurological disorders. Neuropsychiatric Disease and Treatment, 2237-2254
9. He, W., Ding, J., Gao, N., Zhu, L., Zhu, L., & Feng, J. (2024). Elucidating the toxicity mechanisms of organophosphate esters by adverse outcome pathway network. Archives of Toxicology, 98(1), 233-250.
10. Ung, S. P. M., & Li, C. J. (2023). From rocks to bioactive compounds: a journey through the global P (V) organophosphorus industry and its sustainability. RSC Sustainability, 1(1), 11-37.
11. Jessen, H. J., Ahmed, N., & Hofer, A. (2014). Phosphate esters and anhydrides–recent strategies targeting natures favoured modifications. Organic & biomolecular chemistry, 12(22), 3526-3530.
12. Demkowicz, S., Rachon, J., Daśko, M., & Kozak, W. (2016). Selected organophosphorus compounds with biological activity. Applications in medicine. RSC advances, 6(9), 7101-7112.
13. Wang, Y., Zhao, Y., Han, X., Wang, J., Wu, C., Zhuang, Y., ... & Li, W. (2023). A review of organophosphate esters in aquatic environments: levels, distribution, and human exposure. Water, 15(9), 1790.
14. Wang, X., Zhong, W., Xiao, B., Liu, Q., Yang, L., Covaci, A., & Zhu, L. (2019). Bioavailability and biomagnification of organophosphate esters in the food web of Taihu Lake, China: Impacts of chemical properties and metabolism. Environment International, 125, 25-32.
15. Wei, G. L., Li, D. Q., Zhuo, M. N., Liao, Y. S., Xie, Z. Y., Guo, T. L., ... & Liang, Z. Q. (2015). Organophosphorus flame retardants and plasticizers: sources, occurrence, toxicity and human exposure. Environmental pollution, 196, 29-46.
16. Liu, Y., Gong, S., Ye, L., Li, J., Liu, C., Chen, D., ... & Su, G. (2021). Organophosphate (OP) diesters and a review of sources, chemical properties, environmental occurrence, adverse effects, and future directions. Environment international, 155, 106691.
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Published
2024-12-19
How to Cite
Sheetal Meena, Dr. Asha Verma, & Dr. Manju Singh. (2024). Synthesis of Mono and Di -2,6-Dichloro-3- Methyl aniline Organophosphate esters and Characterization by FTIR Spectroscopy and Biological Activity – Acute Oral Toxicity Study. Revista Electronica De Veterinaria, 25(2), 2564-2579. https://doi.org/10.69980/redvet.v25i2.2320
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