Potential Health Risks of Chloroacetanilide Herbicides: An In Silico Analysis

Year 2023, Volume: 27 Issue: 4, 865 - 871, 25.08.2023

Ahmet Ali BERBER Şefika Nur DEMİR Nihan AKINCI KENANOĞLU

https://doi.org/10.16984/saufenbilder.1281720

Abstract

The extensive use of herbicidal products in agriculture and forestry has raised concerns over potential adverse effects on human health and the environment. Chloroacetanilide herbicides are a group of synthetic chemicals used to control weeds in agriculture and forestry. However, so[me of their members have been characterized as possible carcinogens. The genotoxicity and carcinogenicity of two chloroacetanilide herbicides, delachlor and xylachlor, are discussed. This article proposes to use tools to predict their potential toxicities based on their chemical structure. Four software tools, Vega Hub, Toxtree, Lazar, and TEST, are used to predict the potential genotoxic and carcinogenic effects of the herbicides. Vega Hub uses QSAR models, Toxtree uses a decision tree approach, Lazar uses data mining algorithms, and TEST uses QSAR methods to estimate toxicity. The canonical Simplified Molecular Input Line Entry Specification (SMILES) systems of delachlor and xylachlor are entered into each software tool to create a prediction. The study found that delachlor and xylachlor is a class 3 highly toxic compounds with potential mutagenic and carcinogenic effects based on Toxtree and Vega Hub. Meanwhile, Lazar and TEST predicted that delachlor and xylachlor are unlikely to be mutagenic. This study to determine the toxicity of the herbicides delachlor and xylachlor has shown that the possible effects of these herbicides on health and the environment need to be further investigated. The results provide valuable insights into chloroacetanilide herbicide toxicity and help develop safer, more environmentally friendly alternatives.

Keywords

Genotoxicity, carcinogenicity, in silico, chloroacetanilide herbicides

References

• A. De, R. Bose, A. Kumar, S. Mozumdar, “Worldwide Pesticide Use”. In: Targeted Delivery of Pesticides Using Biodegradable Polymeric Nanoparticles. SpringerBriefs in Molecular Science. Springer, New Delhi, 5-6, 2014.
• B. Alewu, C. Nosiri, “Pesticides and human health,” Pesticides in the modern world–effects of pesticides exposure. InTech, pp. 231–50, 2011.
• World Health Organization (WHO), “Public health impact of pesticides used in agriculture”. World Health Organization, 1990. [Online]. Available: https://apps.who.int/iris/handle/10665/39772
• W. Yang, B. A. Holmén, “Relative effects of surfactants and humidity on soil/air desorption of chloroacetanilide and dinitroaniline herbicides,” Environmental science & technology, vol. 42, no. 18, pp. 6843–6848, 2008.
• W. Liu, J. Gan, S. K. Papiernik, S. R. Yates, “Structural Influences in Relative Sorptivity of Chloroacetanilide Herbicides on Soil,” Journal of Agricultural and Food Chemistry, vol. 48, no. 9, pp. 4320–4325, 2000.
• K. L. Dearfield, N. E. McCarroll, A. Protzel, H. F. Stack, M. A. Jackson, M. D. Waters, “A survey of EPA/OPP and open literature on selected pesticide chemicals: II. Mutagenicity and carcinogenicity of selected chloroacetanilides and related compounds,” Mutation Research/Genetic Toxicology and Environmental Mutagenesis, vol. 443, no. 1–2, pp. 183–221, 1999.
• J. D. Coates, R. A. Bruce, J. D. Haddock, “Anoxic bioremediation of hydrocarbons,” Nature, vol. 396, no. 6713, pp. 730–730, 1998.
• J. Ashby, L. Kier, A. Wilson, T. Green, P. Lefevre, H. Tinwell, G. Willis, W. Heydens, M. Clapp. “Evaluation of the Potential Carcinogenicity and Genetic Toxicity to Humans of the Herbicide Acetochlor.” Human & Experimental Toxicology, vol. 15, no. 9: pp. 702–35, 1996.
• H. Bian, J. Chen, X. Cai, P. Liu, Y. Wang, L. Huang, X. Qiao, and C. Hao, “Dechlorination of chloroacetanilide herbicides by plant growth regulator sodium bisulfite,” Water Research, vol. 43, no. 14, pp. 3566–3574, Aug. 2009.
• P. J. Dierickx, “Glutathione- dependent cytotoxicity of the chloroacetanilide herbicides alachlor, metolachlor, and propachlor in rat and human hepatoma-derived cultured cells,” Cell biology and toxicology, vol. 15, pp. 325–332, 1999.
• S. Furukawa, T. Harada, D. Thake, M. J. Iatropoulos, J. H. Sherman, “Consensus diagnoses and mode of action for the formation of gastric tumors in rats treated with the chloroacetanilide herbicides alachlor and butachlor,” Toxicologic Pathology, vol. 42, no. 2, pp. 386–402, 2014.
• K. A. Lewis, J. Tzilivakis, D. J. Warner, A. Green, “An international database for pesticide risk assessments and management,” Human and Ecological Risk Assessment: An International Journal, vol. 22, no. 4, pp. 1050–1064, 2016.
• OECD, “Fundamental and guiding principles for (Q) SAR analysis of chemical carcinogens with mechanistic considerations,” Series on testing and assessment. 2015. [Online]. Available: https://one.oecd.org/document/env/jm/mono(2015)46/en/pdf
• G. J. Myatt, E. Ahlberg, Y. Akahori, D. Allen, A. Amberg, L. T. Anger, A. Aptula, S. Auerbach, L. Beilke, P. Bellion, R. Benigni, J. Bercu, E. D. Booth, D. Bower, A. Brigo, N. Burden, Z. Cammerer, M. T. D. Cronin, K. P. Cross, et al., “In silico toxicology protocols,” Regulatory Toxicology and Pharmacology, vol. 96, pp. 1–17, 2018.
• H.-J. Klimisch, M. Andreae, U. Tillmann, “A Systematic Approach for Evaluating the Quality of Experimental Toxicological and Ecotoxicological Data,”Regulatory Toxicology and Pharmacology, vol. 25, no. 1, pp. 1–5, 1997.
• E. Benfenati, A. Manganaro, G. C. Gini, “VEGA-QSAR: AI inside a platform for predictive toxicology.,” PAI@ AI* IA, vol. 1107, pp. 21–28, 2013.
• G. Patlewicz, N. Jeliazkova, R. J. Safford, A. P. Worth, B. Aleksiev, “An evaluation of the implementation of the Cramer classification scheme in the Toxtree software,” SAR and QSAR in Environmental Research, vol. 19, no. 5–6, pp. 495–524, 2008.
• A. Maunz, M. Gütlein, M. Rautenberg, D. Vorgrimmler, D. Gebele, C. Helma, “Lazar: a modular predictive toxicology framework”. Frontiers in pharmacology, 4, 38, 2013.
• T. M. Martin, “User’s Guide for T.E.S.T. (Toxicity Estimation Software Tool)”, 2020.
• PubChem, “Delachlor.” https://pubchem.ncbi.nlm.nih.gov/compound/32321 (accessed Apr. 02, 2023).
• PubChem, “Xylachlor.” https://pubchem.ncbi.nlm.nih.gov/compound/162992 (accessed Apr. 02, 2023).
• T. Tralau, M. Oelgeschläger, R. Gürtler, G. Heinemeyer, M. Herzler, T. Höfer, H. Itter, T. Kuhl, N. Lange, N. Lorenz, C. Müller-Graf, U. Pabel, R. Pirow, V. Ritz, H. Schafft, H. Schneider, T. Schulz, D. Schumacher, S. Zellmer, G. Fleur-Böl, M. Greiner, M. Lahrssen-Wiederholt, A. Lampen, A. Luch, G. Schönfelder, R. Solecki, R. Wittkowski, A. Hensel, “Regulatory toxicology in the twenty-first century: challenges, perspectives and possible solutions”. Archives of Toxicology, vol. 89, 823–850, 2015.
• USEPA, “Inventory of US greenhouse gas emissions and sinks: 1990–2011. EPA-430-R-13-001,” 2013.
• M. Cheng, Q. Meng, Y. Yang, C. Chu, Q. Chen, Y. Li, D. Cheng, Q. Hong, X. Yan, J. He, “The Two-Component Monooxygenase MeaXY Initiates the Downstream Pathway of Chloroacetanilide Herbicide Catabolism in Sphingomonads”. Applied and Environmental Microbiology, 83, 2017.
• N. Wan, G. Lin, “Parkinson’s disease and pesticides exposure: new findings from a comprehensive study in Nebraska, USA,” The Journal of Rural Health, vol. 32, no. 3, pp. 303–313, 2016.
• B. Hill, P. R. Jefferies, G. B. Quistad, J. E. Casida, “Dialkylquinoneimine metabolites of chloroacetanilide herbicides induce sister chromatid exchanges in cultured human lymphocytes,” Mutation Research/Genetic Toxicology and Environmental Mutagenesis, vol. 395, no. 2–3, pp. 159–171, 1997.
• T. Green, R. Lee, R. B. Moore, J. Ashby, G. A. Willis, V. J. Lund, M. J. L. Clapp, “Acetochlor-induced rat nasal tumors: further studies on the mode of action and relevance to humans”. Regulatory Toxicology and Pharmacology, vol. 32, no. 1, 127-133, 2000.
• B. Ateeq, M. A. Farah, W. Ahmad, “Detection of DNA damage by alkaline single cell gel electrophoresis in 2, 4-dichlorophenoxyacetic-acid-and butachlor-exposed erythrocytes of Clarias batrachus,” Ecotoxicology and environmental safety, vol. 62, no. 3, pp. 348–354, 2005.
• C. D. Nwani, U. I. Ama, F. Okoh, U. O. Oji, R. C. Ogbonyealu, A. A. Ibiam, O. Udu-Ibiam, “Acute toxicity of the chloroacetanilide herbicide butachlor and its effects on the behavior of the freshwater fish Tilapia zillii”. African journal of biotechnology, vol. 12, no. 5, 2013.