Quantitative structure-activity relationships for the toxicity of organophosphorus and carbamate pesticides to the rainbow trout Onchorhyncus mykiss

Pest Management Science

Volumn 62, Issue 9, 2006, Pages 819-831

  Bermúdez Saldaña, José M ^a   Cronin, Mark T D ^b  

^a UNIVERSITY OF VALENCIA   (Spain)

^b LIVERPOOL JOHN MOORES UNIVERSITY   (United Kingdom)

Author keywords

Carbamate; Onchorhyncus mykiss; Organophosphorus; Pesticide; Quantitative structure activity relationships; Rainbow trout; Toxicity

Indexed keywords

CARBAMIC ACID DERIVATIVE; CHOLINESTERASE INHIBITOR; ORGANOPHOSPHORUS COMPOUND; PESTICIDE;

CARBAMATE; DATABASE; FISH; MULTIPLE REGRESSION; ORGANOPHOSPHATE; PESTICIDE; QUANTITATIVE ANALYSIS; TOXICITY;

ANIMAL; ARTICLE; CHEMISTRY; CLASSIFICATION; MULTIVARIATE ANALYSIS; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RAINBOW TROUT; RISK ASSESSMENT; STATISTICAL MODEL;

ANIMALS; CARBAMATES; CHOLINESTERASE INHIBITORS; LINEAR MODELS; MULTIVARIATE ANALYSIS; ONCORHYNCHUS MYKISS; ORGANOPHOSPHORUS COMPOUNDS; PESTICIDES; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; RISK ASSESSMENT;

MYKISS; ONCORHYNCHUS MYKISS;

EID: 33748417568     PISSN: 1526498X     EISSN: 15264998     Source Type: Journal    
DOI: 10.1002/ps.1233     Document Type: Article

References (37)

1. Pesticide Action Network UK (PAN UK), http://www.pan-uk.org/pestnews/ pn68/pn68p9.htm (accessed August 2005).
2. US Environmental Protection Agency, Pesticide Market Estimates, http://www.epa.gov/oppbead1/pestsales/01pestsales/table_of_contents2001.html (accessed August 2005).
3. Zeren O, Dikmen N and Taga S, Measuring the exposure to organophosphorus insecticides of people involved in crop protection in Turkey. Agr Ecosyst Environ 93:447-448 (2002).
4. Nigg HN and Knaak JB, Blood cholinesterases as human biomarkers of organophosphorus pesticide exposure. Rev Environ Contam Toxicol 163:29-111 (2000).
5. Vittozzi L, Fabrizi L, Di Consiglio E and Testai E, Mechanistic aspects of organophosphorothionate toxicity in fish and humans. Environ Internat 26:125-129 (2001).
6. Tougu V and Kesvatera T, Role of ionic interactions in cholinesterase catalysis. Biochim Biophys Acta 1298:12-30 (1996).
7. Lin G, Lai CY and Liao WC, Molecular recognition by acetylcholinesterase at the peripheral anionic site: structure-activity relationships for inhibitions by aryl carbamates. Bioorgan Med Chem 7:2683-2689 (1999).
8. Kasagami T, Miyamoto T and Yamamoto I, Activated transformations of organophosphorus insecticides in the case of non-AChE inhibitory oxons. Pest Manag Sci 58:1107-1117 (2002).
9. Rao JV, Effects of monocrotophos and its analogs in acetylcholinesterase activity's inhibition and its pattern of recovery on euryhaline fish, Oreochromis mossambicus. Ecotox Environ Safe 59:217-222 (2004).
10. Cronin MTD, Walker JD, Jaworska JS, Comber MHI, Watts CD and Worth AP, Use of QSARs in international decision-making frameworks to predict ecologic effects and environmental fate of chemical substances. Environ Health Perspect 111:1376-1390 (2003).
11. Russom CL, Bradbury SP, Broderius SJ, Hammermeister DE and Drummond RA, Predicting modes of toxic action from chemical structure: acute toxicity in the Fathead minnows (Pimephales promelas). Environ Toxicol Chem 16:948-967 (1997).
12. Bradbury SP, Henry TR and Carlson RW, Fish acute toxicity syndromes in the development of mechanism-specific QSARs, in Practical Applications of Quantitative Structure-Activity Relationships (QSAR) in Environmental Chemistry and Toxicology, ed. by Karcher W and Devillers J. Kluwer, Dordrecht, pp. 295-315 (1990).
13. Hermens J, Prediction of environmental toxicity based on structure-activity relationships using mechanistic information. Sci Total Environ 171:235-242 (1995).
14. EC, 1996. Technical Guidance Document in support of Commission Directive 93/67/EEC on Risk Assessment for New Notified Substances, Commission Regulation (EC) No. 1488/94 on Risk Assessment for Existing Substances and Directive 98/8/EC of the European Parliament and of the Council concerning the placing of biocidal products on the market; http://ecb.jrc.it/index.php?CONTENU=/Technical- Guidance-Document/sommaire.php (accessed February 2005).
15. Cronin MTD and Dearden JC, QSAR in toxicology. 1. Prediction of aquatic toxicity. Quant Struct-Act Relat 14:1-7 (1995).
16. Könemann H, Quantitative structure-activity relationships in fish toxicity studies. Part 1: relationship for 50 industrial pollutants. Toxicology 19:209-221 (1981).
17. Veith GD, Call DJ and Brooke LT, Structure-toxicity relationships for the fathead minnow, Pimephales promelas: narcotic industrial chemicals. Can J Fish Aquat Sci 40:743-748 (1983).
18. Schultz TW, Cronin MTD, Walker JD and Aptula AO, Quantitative structure-activity relationships (QSARs) in toxicology: a historical perspective. J Mol Struct-Theochem 622:1-22 (2003).
19. Johnson H, Kenley RA and Rynard C, QSAR for cholinesterase inhibition by organophosphorus esters and CNDO/2 calculations for organophosphorus ester hydrolysis. Quant Struct-Act Relat 4:172-180 (1985).
20. Hermens J, De Bruijn J, Pauly J and Seinen W, QSAR studies for fish toxicity data of organophosphorus compounds and other classes of reactive organic compounds, in QSAR in Environmental Toxicology-II, ed. by Kaiser KLE. Reidel, Dordrecht, pp. 135-152 (1987).
21. Verhaar IQM, Eriksson L, Sjostrom M, Schuurmann G, Seinen W and Hermens JLM, Modelling the toxicity of organophosphates: a comparison of the multiple linear regression and PLS regression method. Quant Struct-Act Relat 13:133-143 (1994).
22. Freidig AP and Hermens JLM, Narcosis and chemical reactivity QSARs for acute fish toxicity. Quant Struct-Act Relat 19:547-553 (2000).
23. ECOTOX database, US EPA, Mid-Continent Ecology Division, Duluth, MN (MED-Duluth), http://www.epa.gov/ecotox (accessed February 2005).
24. Cronin MTD and Schultz TW, Pitfalls in QSAR. J Mol StrucTheochem 622:39-51 (2003).
25. Cronin MTD, Toxicological information for use in predictive modeling: quality, sources and databases, in Predictive Toxicology, ed. by Helma C. Taylor and Francis, Boca Raton, FL, USA, pp. 93-133 (2005).
26. PhysProp Database, Syracuse Research Corporation (SRC), http://esc.syrres.com/intekow/PhysProp.htm (accessed February 2005).
27. PhysProp Database, Syracuse Research Corporation (SRC), http://www.syrres.com/esc/est_soft.htm (accessed February 2005).
28. Tremolada P, Finizio A, Villa S, Gaggi C and Vighi M, Quantitative inter-specific chemical activity relationships of pesticides in the aquatic environment. Aguat Toxicol 67:87-103 (2004).
29. Eriksson L, Jaworska J, Worth AP, Cronin MTD, McDowell RM and Gramatica P, Methods for reliability and uncertainty assessment and for applicability evaluations of classification- and regression-based QSARs. Environ Health Perspect 111:1361-1375 (2003).
30. Eriksson L, Johansson E, Kettaneh-Wold N and Wold S, Multi-and megavariate data analysis - principles and applications. Urnea, Sweden (2001).
31. Cronin MTD, Aptula AO, Duffy JC, Netzeva TI, Rowe PH, Valkova IV, et al, Comparative assessment of methods to develop QSARs for the prediction of the toxicity of phenols to Tetrahymena pyriformis. Chemosphere 49:1201-1221 (2002).
32. Lipnick RL, Base-line toxiciry predicted by quantitative structure-activity relationships as a probe for molecular mechanism of toxicity, in Probing Bioactive Mechanisms, ed. by Magee PS, Henry DR and Block JH. American Chemical Society, Washington, DC, pp. 366-389 (1989).
33. Verhaar HJM, Solbé J, Speksnijder J, van Leeuwen CJ and Hermens JLM, Classifying environmental pollutants. Part 3. External validation of the classification system. Chemosphere 40:875-883 (2000).
34. El Yazal J, Rao SN, Mehl A and Slikker W, Prediction of organophosphorus acetylcholinesterase inhibition using three-dimensional quantitative structure-activity relationship (3D-QSAR) methods. Toxicol Sci 63:223-232 (2001).
35. Ren S, Ecotoxicity prediction using mechanism- and non-mechanism-based QSARs: a preliminary study. Chemosphere 53:1053-1065 (2003).
36. Aptula AO, Jeliazkova NG, Schultz TW and Cronin MTD, The better predictive model: high q2 for the training set or low root mean square error of prediction for the test set? QSAR Comb Sci 24:385-396 (2005).
37. Lipnick RL, Outliers: their origin and use in the classification of molecular mechanisms of toxicity. Sci Total Environ 109-110:131-153 (1991).