Herbicides have widely variable toxicity and many of them are persistent soil contaminants. Acetanilide and triazine family of herbicides have widespread use, but increasing interest for the development of new herbicides has been rising to increase their effectiveness and to diminish environmental hazard. The environmental risk of new herbicides can be accessed by estimating their soil sorption (logKoc), which is usually correlated to the octanol/water partition coefficient (logKow). However, earlier findings have shown that this correlation is not valid for some acetanilide and triazine herbicides. Thus, easily accessible quantitative structure–property relationship models are required to predict logKoc of analogues of the these compounds. Octanol/water partition coefficient, molecular weight and volume were calculated and then regressed against logKoc for two series of acetanilide and triazine herbicides using multiple linear regression, resulting in predictive and validated models.
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Ackerman F (2007) The economics of atrazine. Int J Occup Environ Health 13:437–445
Brown RD, Martin YC (1997) The information content of 2D and 3D structural descriptors relevant to ligand-receptor binding. J Chem Inf Comp Sci 37:1–9
Corsonlini S, Ademollo N, Romeo T, Greco S, Focardi S (2005) Persistent organic pollutants in edible fish: a human and environmental health problem. Microchem J 79:115–123
Cramer RD, Patterson DE, Bunce JD (1988) Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins. J Am Chem Soc 110:5959–5967
Domingo JL (2004) Human exposure to polybrominated diphenyl ethers through the diet. J Chromatogr A 1054:321–326
Estrada E, Molina E, Perdomo-López I (2001) Can 3D structural parameters be predicted from 2D (topological) molecular descriptors? J Chem Inf Comp Sci 41:1015–1021
Freitas MR, Matias SVBG, Macedo RLG, Freitas MP, Venturin N (2013) Augmented multivariate image analysis applied to quantitative structure-activity relationship modeling of the phytotoxicities of benzoxazinone herbicides and related compounds on problematic weeds. J Agric Food Chem 61:8499–8503
Gerstl Z (1990) Estimation of organic chemical sorption by soils. J Cont Hydrol 6:357–375
Giesy JP, Ludwig JP, Tillitt DE (1994) Deformities in birds of the Great-Lakes region assigning causality. Environ Sci Technol 28:A128–A135
Kavlock RJ, Daston GP, Derosa C, Fenner-Crisp P, Gray LE, Kaattari S, Lucier G, Luster M, Mac MJ, Maczka C, Miller R, Moore J, Rolland R, Scott G, Sheehan DM, Sinks T, Tilson HA (1996) Research needs for the risk assessment of health and environmental effects of endocrine disruptors: a report of the US EPA-sponsored workshop. Environ Health Persp 104:715–740
Kelce WR, Stone CR, Laws SC, Gray LE, Kemppainen JA, Wilson EM (1995) Persistent DDT metabolite P, P’-DDE is a potent androgen receptor antagonist. Nature 375:581–585
Klebe G, Abraham U, Mietzner T (1994) Molecular similarity indices in a comparative analysis (CoMSIA) of drug molecules to correlate and predict their biological activity. J Med Chem 37:4130–4146
Mitra I, Saha A, Roy K (2010) Exploring quantitative structure-activity relationship studies of antioxidant phenolic compounds obtained from traditional Chinese medicinal plants. Mol Simul 36:1067–1079
Nunes CA, Freitas MP, Pinheiro ACM, Bastos SC (2012) Chemoface: a novel free user-friendly interface for chemometrics. J Braz Chem Soc 23:2003–2010
Prosen H (2012) Fate and determination of triazine herbicides in soil, herbicides: properties, synthesis and control of weeds, ed. by Hasaneen MN, InTech. Available from: http://www.intechopen.com/books/herbicides-properties-synthesis-and-control-of-weeds/fateand-determination-of-triazine-herbicides-in-soil
Ratcliffe DA (1967) Decrease in eggshell weight in certain birds of prey. Nature 215:208–210
Ratcliffe DA (1970) Changes attributable to pesticides in egg breakage frequency and eggshell thickness in some British birds. J Appl Ecol 7:67–115
Sabljić A, Güsten H, Verhaar H, Hermens J (1995) QSAR modelling of soil sorption. Improvements and systematics of logKOC versus logKOW correlations. Chemosphere 31:4489–4514
Schüürmann G, Ebert R-U, Kühne R (2006) Prediction of the sorption of organic compounds into soil organic matter from molecular structure. Environ Sci Technol 40:7005–7011
Stamper DM, Tuovinen OH (1998) Biodegradation of the acetanilide herbicides alachlor, metolachlor, and propachlor. Crit Rev Microbiol 24:1–22
Authors are thankful to FAPEMIG and CNPq for the financial support, studentship (to M.R.F. and S.V.B.G.M.) and fellowships (to R.L.G.M., M.P.F. and N.V.).
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Freitas, M.R., Matias, S.V.B.G., Macedo, R.L.G. et al. Three-Parameter Modeling of the Soil Sorption of Acetanilide and Triazine Herbicide Derivatives. Bull Environ Contam Toxicol 92, 143–147 (2014). https://doi.org/10.1007/s00128-013-1184-3
- Environmental risk
- QSPR modeling
- Soil sorption