Selection of representative congener for polychlorinated trans-azobenzenes (PCt-ABs) based on comprehensive thermodynamical and quantum-chemical characterization

Journal of Environmental Science and Health - Part B Pesticides, Food Contaminants, and Agricultural Wastes

Volumn 41, Issue 7, 2006, Pages 1131-1142

  Wilczyńska Piliszek, Agata ^a   Puzyn, Tomasz ^a   Piliszek, Sławomir ^a   Falandysz, Jerzy ^a  

^a UNIVERSITY OF GDA SK   (Poland)

Author keywords

3,3 ,4,4 Tetrachloro trans azobenzene (TeCt AB); Herbicide; Multidimensional analysis; PCt ABs; Quantum Chemical properties; Toxicity

Indexed keywords

CHARGED PARTICLES; CHLORINE COMPOUNDS; HERBICIDES; MOLECULAR WEIGHT; PRINCIPAL COMPONENT ANALYSIS; THERMODYNAMICS; TOXICITY;

3,3′,4,4′-TETRACHLORO-TRANS-AZOBENZENE (TECT-AB); MULTIDIMENSIONAL ANALYSIS; PCT-ABS; QUANTUM CHEMICAL PROPERTIES;

AROMATIC COMPOUNDS;

3,4 DICHLOROANILINE; AZOBENZENE DERIVATIVE; HERBICIDE; POLYCHLORINATED AZOBENZENE; UNCLASSIFIED DRUG;

HERBICIDE; PRINCIPAL COMPONENT ANALYSIS; THERMODYNAMICS; THREE-DIMENSIONAL MODELING;

ARTICLE; ATOM; CHEMICAL STRUCTURE; ENERGY; LIPOPHILICITY; MOLECULAR WEIGHT; PRINCIPAL COMPONENT ANALYSIS; QUANTUM CHEMISTRY; STRUCTURE ANALYSIS; THERMODYNAMICS; TRANS ISOMER;

CHLOROBENZENES; DIOXINS; ENVIRONMENTAL POLLUTANTS; HERBICIDES; PRINCIPAL COMPONENT ANALYSIS; THERMODYNAMICS;

EID: 33747682289     PISSN: 03601234     EISSN: 15324109     Source Type: Journal    
DOI: 10.1080/03601230600856835     Document Type: Article

References (28)

1. Ambrus, A.; Hamilton, D.J.; Kuiper, H.A.; Racke, K.D. Significance of impurities in the safety evaluation of crop protection products. Pure Appl. Chem. 2003, 75 (7), 937-973.
2. Taylor, J.S.; Wuthrich, R.C.; Lloyd, K.M.; Poland, A. Chloracne from manufacture of a new herbicide. Archives of Dermatology 1977, 113, 616-619.
3. Hashimoto, S.; Schneider, S.; Morita, M. Levels of 3,3′,4,4′- tetrachloroazobenzene in herbicides and bulk reagents. Chemosphere 1993, 26 (12), 2161-2165.
4. Hill, R.H.; Rollen, Z.J.; Kimbrough, R.D.; Groce, D.F.; Needham, L.L. Tetrachloroazobenzene in 3,4-Dichloroaniline and Its Herbicidal Derivatives: Propanil, Diuron, Linuron, and Neburon. Archives of Environmental Health 1981, 36 (1), 11-14.
5. Bartha, R.; Pramer, D. Transformation of the Herbicide Methyl-N-(3,4-dichlorophenyl)-carbamate (Swep) in soil. Bulletin of Environmental Contamination and Toxicology 1969, 4 (4), 240-245.
6. Bordeleau, L.M.; Bartha, R. Azobenzene Residues from Aniline-based Herbicides; Evidence for Labile Intermediates. Bulletin of Environmental Contamination and Toxicology 1970, 5, 34-37.
7. Kearney, P.C.; Smith, R.J.; Plimmer, J.R.; Guardia, F.S. Propanil and TCAB residues in rice soils. Weed Science 1970, 18 (4), 464-466.
8. Perera, A.; Burleigh, J.R.; Davis, C.B. Movement and retention of propanil N-(3,4-dichlorophenyl)propanamide in a paddy-riverine wetland system in Sri Lanka. Agriculture, Ecosystems and Environment 1999, 72, 255-263.
9. National Registration Authority for Agricultural and Veterinary Chemicals. Diuron. Review Scope Document. Canberra, Australia 2002, 1-23.
10. Miller, G.C.; Zisook, R.; Zepp, R. Photolysis of 3,4-dichloroaniline in natural waters. Journal of Agricultural and Food Chemistry 1980, 28, 1053-1056.
11. Ziegler, T.L.; Pillai, U.A.; Smith, R.L.; Katting, M.J.; Lieber, D.C.; Mayersohn, M.; Sipes, I.G. Absorption and disposition kinetics of 3,3′,4,4-tetrachloroazoxybenzene in the male fischer 344 rat. Drug Metabolism and Disposition 1996, 24 (2), 1009-1014.
12. Van Birgelen, A.P.J.M. 3,3′,4,4′-tetrachloroazobenzene. Toxicology Report Series Number 65; U.S. Department of Health and Human Services, Public Health Service National Institutes of Health NTP, National Toxicology Program: Research Triangle Park, N.C., 1998.
13. Schrankel, K.R.; Hsia, M.T.S.; Pounds, J.G. Hepatocellular pathotoxicology of 3,3′,4,4′-tetrachloroazobenzene and 3,3′,4,4-tetrachloroazoxybenzene in the rodent. Research Communications in Chemical Pathology and Pharmacology 1980, 28 (3), 527-540.
14. Witt, K.L.; Zeiger, E.; Tice, R.R.; Van Birgelen, A.P.J.M. The genetic toxicity of 3,3′,4,4′-tetrachloroazobenzene and 3,3′,4, 4′-tetrachloroazoxybenzene: Discordance between acute mouse bone marrow and subchronic mouse peripheral blood micronucleus test results. Mutation Research 2000, 472, 147-154.
15. Schrankel, K.R.; Kreamer, B.L.; Hsia, M.T.S. Embryotoxicity of 3,3′,4,4′-tetrachloroazobenzene and 3,3′4,4′- tetrachloroazoxybenzene in the Chick Embryo. Archives of Environmental Contamination and Toxicology 1982, 11, 195-202.
16. Hsia, M.T.S.; Bairstow, F.V.Z.; Shih, L.C.T.; Pounds, J.G.; Allen, J.R. 3,4,3′,4′-Tetrachloroazobenzene: A potential environmental toxicant. Research Communications in Chemical Pathology and Pharmacology 1977, 17, 225-236.
17. Taylor, J.S.; Lloyd, K.M. Chloracne from 3,3′4,4′- Tetrachloroazobenzene and 3,3′4,4′-Tetrachloroazoxybenzene Update and Review. Chlorinated Dioxins and Related Compounds. Pergamon Series: Environmental Science 1982, 535-544.
18. Poland, A.; Glover, E.; Kende, A.S.; DeCamp, M.; Giandomenico, C.M. 3,4,3′,4′-tetrachloroazoxybenzene and azobenzene: Potent inducers of aryl hydrocarbon hydroxylase. Science 1976, 194, 627-630.
19. Ochterski, J.W. Thermochemistry in Gaussian; Gaussian, Inc.: 2000; 1-19.
20. Curtiss, L.A.; Raghavachari, K.; Redfern, P.C.; Pople, J.A. Assessment of Gaussian-2 and density functional theories for the computation of enthalpies of formation. J. Chem. Phys 1997, 106 (3), 1063-1079.
21. Chase, M.W.; Davies, C.A.; Downey, J.R.; Frurip, D.J.; McDonald, R.A.; Syverud, A.N. JANAF Thermochemical Tables. 3rd ed. J. Phys. Chem. Ref. Data 1985, 14, Suppl. No. 1.
22. Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; Scuseria, G.E.; Robb, M.A.; Cheeseman, J.R.; Montgomery, J.A.; Vreven, T.; Kudin, K.N.; Burant, J.C.; Millam, J.M.; Iyengar, S.S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G.A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, Y.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J.E.; Hratchian, H.P.; Cross, J.B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R.E.; Yazyev, O.; Austin, A.J.; Cammi, R.; Pomelli, C.; Ochterski, J.W.; Ayala, P.Y.; Morokuma, K.; Voth, G.A.; Salvador, P.; Dannenberg, J.J.; Zakrzewski, V.G.; Dapprich, S.; Daniels, A.D.; Strain, M.C.; Farkas, O.; Malick, D.K.; Rabuck, A.D.; Raghavachari, K.; Foresman, J.B.; Ortiz, J.V.; Cui, Q.; Baboul, A.G.; Clifford, S.; Cioslowski, J.; Stefanov, B.B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R.L.; Fox, D.J.; Keith, T.; Al-Laham, M.A.; Peng, C.Y.; Nanayakkara, A.; Challacombe, M.; Gill, P.M.W.; Johnson, B.; Chen, W.; Wong, M.W.; Gonzalez, C.; Pople, J.A. GAUSSIAN 03; Gaussian Inc.: Pittsburgh, 2003.
23. Todeschini, R.; Consonni, V. Handbook of molecular descriptors; Willey-VCH, Weinheim: 2000.
24. Todeschini, R.; Consonni, V.; Mauri, A.; Pavan, M. DRAGON; Milano Chemometrics: Milano, Italy, 2003.
25. Mazerski, J. Podstawy chemometrii (in Polish); Wydawnictwo Politechniki Gdańskiej: Gdańsk, 2000.
26. StatSoft, Inc. Electronic Statistics Textbook. Tulsa, OK, StatSoft 2006, http://www. statsoft.com/textbook/stathome.html.
27. Eriksson, L.; Tysklind, M. A multivariate approach to risk assessment of environmentally occurring chemicals. Math. Comput. Modelling 1995, 21 (9), 49-54.
28. Tysklind, M.; Andersson, P.; Haglund, P.; Van Bavel, B.; Rappe, C. Selection of polychlorinated biphenyls for use in quantitative structure-activity modeling. SAR and QSAR in Environmental Research 1995, 4, 11-19.