Modelling physico-chemical properties of (benzo)triazoles, and screening for environmental partitioning

Water Research

Volumn 45, Issue 3, 2011, Pages 1463-1471

  Bhhatarai, B ^a   Gramatica, P ^a  

^a UNIVERSITY OF INSUBRIA   (Italy)

Author keywords

(Benzo)triazoles; Applicability domain; Partitioning; QSPR; REACH

Indexed keywords

CHEMICAL ANALYSIS; CHEMICAL PROPERTIES; GENETIC ALGORITHMS; INDICATORS (CHEMICAL); INDUSTRIAL CHEMICALS; LINEAR REGRESSION; PRINCIPAL COMPONENT ANALYSIS;

(BENZO)TRIAZOLE; APPLICABILITY DOMAIN; ENVIRONMENTAL PARTITIONING; HAZARDOUS CHEMICALS; PARTITIONING; PHYSICOCHEMICAL PROPERTY; PROPERTY; QUANTITATIVE STRUCTURE PROPERTY RELATIONSHIPS; REACH; TARGET SPECIES;

FORECASTING;

BENZOTRIAZOLE DERIVATIVE;

GENETIC ALGORITHM; NONTARGET ORGANISM; NUMERICAL MODEL; ORGANIC POLLUTANT; PARTITIONING; PHYSICOCHEMICAL PROPERTY; PRINCIPAL COMPONENT ANALYSIS; REGRESSION ANALYSIS;

ARTICLE; GENETIC ALGORITHM; LEACHING; MODEL; MULTIPLE LINEAR REGRESSION ANALYSIS; PHYSICAL CHEMISTRY; PREDICTION; PRINCIPAL COMPONENT ANALYSIS; PRIORITY JOURNAL; RESOURCE PARTITIONING; SCREENING;

EID: 78650532205     PISSN: 00431354     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.watres.2010.11.006     Document Type: Article

References (45)

1. ChemID Plus, (accessed 08.04.10). http://chem.sis.nlm.nih.gov/chemidplus.
2. Chen Q., Zhu X.-L., Jiang L.-L., Liu Z.-M., Yang G.-F. Synthesis, antifungal activity and CoMFA analysis of novel 1,2,4-triazolo[1,5-a]pyrimidine derivatives. Eur. J. Med. Chem. 2008, 43:595-603.
3. Consonni V., Ballabio D., Todeschini R. Comments on the definition of the Q2 parameter for QSAR validation. J. Chem. Inf. Model. 2009, 49:1669-1678.
4. Cornell J.S., Pillard D.A., Hernandez M.T. Comparative measures of the toxicity of component chemicals in aircraft deicing fluid. Environ. Tox. Chem. 2000, 19:1465-1472.
5. Cronin M.T.D. The role of hydrophobicity in toxicity prediction. Curr. Comput. Aided Drug Des. 2006, 2:405-413.
6. Dimova V., Ragenovic K.C., Kakurinov V. QSAR of some N1-Aryl/heteroarylaminomethyl/ethyl-1,2,4-triazoles Part II, Antimicrobial activity against Bacillus Subtilis. Int. J. Mol. Sci. 2006, 7:119-129.
7. ECHA, 2009. (accessed 08.04.10). http://apps.echa.europa.eu.
8. Efron B. Bootstrap methods, another look at the jackknife. Ann. Stat. 1979, 7:1-26.
9. EPI suite. (accessed 08.04.10). http://www.epa.gov/oppt/exposure/pubs/episuite.htm.
10. EU FP7 CADASTER, 2009. (accessed 08.04.10). http://www.cadaster.eu.
11. Fishel, F.M., 2010. Pesticide toxicity profile, Triazole pesticides. P#168. (accessed 08.04.10). http://edis.ifas.ufl.edu.
12. Gramatica P., Di Guardo A. Screening of pesticides for environmental partitioning tendency. Chemosphere 2002, 42:947-956.
13. Gramatica P., Papa E. Screening and ranking of POPs for global half-life, QSAR approaches for prioritization based on molecular structure. Environ. Sci. Technol. 2007, 41:2833-2839.
14. Gramatica P., Corradi M., Consonni V. Modelling and prediction of soil sorption coefficients of non-ionic organic pesticides by molecular descriptors. Chemosphere 2000, 41:763-777.
15. Gramatica P., Pilutti P., Papa E. Validated QSAR prediction of OH tropospheric degradability, splitting into training-test set and consensus modeling. J. Chem. Inf. Comput. Sci. 2004, 44:1794-1802.
16. Gramatica P., Giani E., Papa E. Statistical external validation and consensus modeling, A QSPR case study for Koc prediction. J. Mol. Graph. Model. 2007, 25:755-766.
17. Gramatica P. Principles of QSAR models validation, internal and external. QSAR Comb. Sci. 2007, 26:694-701.
18. HPV, 2001. (accessed 08.04.10). http://www.epa.gov/hpv/pubs/summaries/benzo/c13456tp.pdf.
19. HyperChem 7.03 Hypercube, Inc., Florida, USA, 2002. http://www.hyper.com.
20. Kenneke J.F., Mazur C.S., Kellock K.A., Overmyer J.P. Mechanistic approach to understanding the toxicity of the azole fungicide triadimefon to a nontarget aquatic insect and implications for exposure assessment. Environ. Sci. Technol. 2009, 43:5507-5513.
21. Leardi R., Boggia R., Terrile M. Genetic Algorithms as a strategy for feature selection. J. Chemometr. 1992, 6:267-281.
22. Liang C., Gallagher D.A. QSPR prediction of vapor pressure from solely theoretically-derived descriptors. J. Chem. Inf. Comput. Sci. 1998, 38:321-324.
23. Maroni M., Colosio C., Ferioli A., Fait A. Biological monitoring of pesticide exposure, a review. Toxicology 2000, 143:1-122.
24. McNeill K.S., Cancilla D.A. Detection of triazole deicing Additives in soil samples from airports with low, Mid, and large Volume aircraft deicing Activities. Bull. Environ. Contam. Toxicol. 2008, 70:868-875.
25. Mitchell B.E., Jurs P.C. Prediction of aqueous solubility of organic compounds from molecular structure. J. Chem. Inform. Comput. Sci. 1998, 38:489-496.
26. OECD Guidelines. (accessed 08.04.10). http://www.oecd.org/dataoecd/33/37/37849783.pdf.
27. Papa E., Castiglioni S., Gramatica P., Nikolayenko V., Kayumov O., Calamari D. Screening the leaching tendency of pesticides applied in the Amu Darya Basin (Uzbekistan). Water Res. 2004, 38:3485-3494.
28. Partil G.S. Prediction of aqueous solubility and octanol-water partition coefficient for pesticides based on their molecular structure. J. Hazard. Mater. 1994, 36:35-43.
29. REACH, 2007. (accessed 08.04.10). http://ec.europa.eu/environment/chemicals/reach/reach_intro.htm.
30. Sheng C.-Q., Zhang W.-N., Zhang M., Song Y.-L., Chen J., Zhu J., Ji H.-T., Yao J.-Z., Miao Z.-Y. 3D-QSAR study of a series of novel triazole antifungal compounds. Huaxue Xuebao 2005, 63:617-624.
31. Shi L.M., Fang H., Tong W., Wu J., Perkins R., Blair R.M., Branham W.S., Dial S.L., Moland C.L., Sheehan D.M. QSAR models using a large diverse set of estrogens. J. Chem. Inf. Comput. Sci. 2001, 41:186-195.
32. SRC Phys-Prop. (accessed 08.04.10). http://www.syrres.com.
33. Switzenbaum M.S., Veltmanb S., Mericasc D., Wagoner B., Schoenberg T. Best management practices for airport deicing stormwater. Chemosphere 2001, 43:1051-1062.
34. Tetko I.V., Gasteiger J., Todeschini R., Mauri A., Livingstone D., Ertl P., Palyulin V.A., Radchenko E.V., Zefirov N.S., Makarenko A.S., Tanchuk V.Y., Prokopenko V.V. Virtual computational chemistry laboratory - design and description. J. Comput. Aid. Mol. Des 2005, 19:453-463.
35. Tiboni G.M. Second branchial arch anomalies induced by fluconazole, a bis-triazole antifungal agent, in cultured mouse embryos. Res. Commun. Chem. Pathol. Pharmacol. 1993, 79:381-384.
36. Todeschini R., Consonni V. Handbook of Molecular Descriptors 2009, Wiley-VCH, Weinheim, Germany.
37. Todeschini R., Consonni V., Pavan M. MOBY DIGS - Software for Multilinear Regression Analysis and Variable Subset Selection by Genetic Algorithm. Ver. 1.2 for Windows 2002, Talete srl, Milan, Italy.
38. Todeschini R., Consonni V., Mauri A., Pavan M. DRAGON v.5 2007, Talete srl, Milan, Italy. http://www.talete.it.
39. Trapani A., Lopedota A., Denora N., Laquintana V., Franco M., Latrofa A., Trapani G., Liso G. A rapid screening tool for estimating the potential of 2-hydroxypropyl-beta-cyclodextrin complexation for solubilization purposes. Int. J. Pharm. 2005, 295:163-175.
40. Tropsha A., Gramatica P., Gombar V.K. The importance of being earnest, validation is the absolute essential for successful application and interpretation of QSPR models. QSAR Comb. Sci. 2003, 22:69-76.
41. Wei Q.-L., Zhang S.-S., Gao J., Li W., Xu L.-Z., Yu Z.-G. Synthesis and QSAR studies of novel triazole compounds containing thioamide as potential antifungal agents. Bioorg. Med. Chem. 2006, 14:7146-7153.
42. Weiss S., Jakobs J., Reemtsma T. Discharge of three benzotriazole corrosion inhibitors with municipal wastewater and improvements by membrane bioreactor treatment and ozonation. Environ. Sci. Technol. 2006, 40:7193-7199.
43. Xu L.-Z., Yu G.-P., Bi W.-Z., Aisa H.A. A quantitative structure-activity relationship study of antifungal analogues of 3,4-substituted 5-((1H-1, 2, 4-triazol-1-yl)methyl)-4H-1,2,4-triazole. Struct. Chem. 2008, 19:959-965.
44. Yu G.-P., Bi W.-Z., Si G.-D., Yang Y.-X., Aisa H.A., Xu L.-X. Synthesis and QSAR studies on 1-[(5-substituted-1,3,4-thiadiazol-2-yl)methyl]-1H-1,2,4-triazole as antifungal agents. Struct. Chem. 2009, 20:569-576.
45. Zupan J., Novic M., Ruisanchez I. Kohonen and counterpropagation artificial neural networks in analytical chemistry. Chemometrics Intell. Lab. Syst. 1997, 38:1-24.