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This historical page is being kept for research or reference
purposes and will not be updated.

This historical page is being kept for research or reference
purposes and will not be updated.

8. References

Analytical Bio-Chemistry Laboratories. 1990. Chronic toxicity of dibutyltin dichloride to Daphnia magna. Study sponsored by the Consortium of Tributyltin Manufacturers (Administrator: M&T Chemicals, Inc., Woodbridge, New Jersey). Analytical Bio-Chemistry Laboratories, Inc., Columbia, Missouri (ABC Final Report No. 38311).

Becker, E. 1992. Ableitung von Qualitatszielen zum Schutz Oberirdischer Binnengewasser für Organozinnverbindungen: Dibutylzinnverbindungen, Tetrabutylzinn, Tributylzinnverbindungen, Triphenylzinnverbindungen. Umweltbundesamt, Entwurf für den BLAK QZ, Stand 26.3 (Organisation for Economic Co-operation and Development data file) [cited in ECOTOX, available at https://cfpub.epa.gov/ecotox/].

Borghi, V. and C. Porte. 2002. Organotin pollution in deep-sea fish from the northwestern Mediterranean. Environ. Sci. Technol. 36: 4224–4228.

Bryan, G.W., P.E. Gibbs and G.R. Burt. 1988. A comparison of the effectiveness of tri-n-butyltin chloride and five other organotin compounds in promoting the development of imposex in the dogwhelk, Nucella lapillus. J. Mar. Biol. Assoc. U.K. 68: 733–744 [cited in Maguire, 2000].

CCME. 1999. Canadian environmental quality guidelines. Canadian Council of Ministers of the Environment, Winnipeg, Manitoba.

Chau, Y.K., P.T.S. Wong, O. Kramar and G.A. Bengert. 1980. Methylation of tin in the aquatic environment. In: Proceedings of the International Conference on Heavy Metals in the Environment, Amsterdam, September. 4 pp. [cited in Government of Canada, 1993].

Chau, Y.K., R.J. Maguire, M. Brown, F. Yang and S.P. Batchelor. 1997. Occurrence of organotin compounds in the Canadian aquatic environment five years after the regulation of antifouling uses of tributyltin. Water Qual. Res. J. Can. 32: 453–521.

Day, K.E., R.J. Maguire, D. Milani and S.P. Batchelor. 1998. Toxicity of tributyltin to four species of freshwater benthic invertebrates using spiked sediment bioassays. Water Qual. Res. J. Can. 33: 111–132.

de Vries, H., A.H. Penninks, N.J. Snoeij and W. Seinen. 1991. Comparative toxicity of organotin compounds to rainbow trout (Oncorhynchus mykiss) yolk sac fry. Sci. Total Environ. 103: 229–243.

Environment Canada. 2006. Canadian Environmental Protection Act, 1999. Risk assessment of new and transitional organotin substances. New Substances Division, Environment Canada. Draft report, February 2006. 39 pp.

Geiger, D.L., L.T. Brooke and D.J. Call. 1990. Acute toxicities of organic chemicals to fathead minnows (Pimephales promelas). Vol. 5. Center for Lake Superior Environmental Studies, University of Wisconsin–Superior, Superior, Wisconsin. p. 331 [cited in ECOTOX, available at https://cfpub.epa.gov/ecotox/].

Gibbs, P.E., P.L. Pascoe and G.R. Burt. 1988. Sex changes in the female dogwhelk, Nucella lapillus, induced by tributyltin from antifouling paints. J. Mar. Biol. Assoc. U.K. 68: 715–731 [cited in Maguire, 2000].

Gitlitz, M.H. and M.K. Moran. 1983. Tin compounds. In: H.F. Mark, D.F. Othmer, C.G. Overberger and G.T. Seaborg (eds.), Kirk-Othmer encyclopaedia of chemical technology. 3rd ed. Vol. 23. J. Wiley and Sons, Toronto, Ontario. pp. 42–77 [cited in Maguire, 1992; Government of Canada, 1993].

Government of Canada. 1993. Canadian Environmental Protection Act. Priority Substances List assessment report. Non-pesticidal organotin compounds. Environment Canada and Health and Welfare Canada, Ottawa, Ontario. 32 pp.

Government of Canada. 2000. Persistence and Bioaccumulation Regulations. Canada Gazette, Part II, Vol. 134, No. 7, March 29, 2000.

Government of Canada. 2003. Canadian Environmental Protection Act. Follow-up Report on a PSL 1 Substance for Which Data Were Insufficient to Conclude Whether the Substance Was “Toxic” to Human Health, Non-pesticidal Organotin Compounds, May, 2003.

Huang, G., Z. Bai, S. Dai and Q. Xie. 1993. Accumulation and toxic effects of organometallic compounds on algae. Appl. Organomet. Chem. 7: 373–380.

Huang, G., S. Dai and H. Sun. 1996. Toxic effects of organotin species on algae. Appl. Organomet. Chem. 10: 377–387.

Hunziker, R.W., B.I. Escher and R.P. Schwarzenbach. 2001. pH-dependence of partitioning of triphenyltin and tributyltin between phosphatidylcholine liposomes and water. Environ. Sci. Technol. 35: 3899–3904.

IUCLID. 2002a. IUCLID data set: 3-Ethylhexyl-4,4-dibutyl-10-ethyl-7-oxo-8-oxa-3,5-dithia-4-stannatetradecanoate. International Uniform Chemical Information Database, European Chemicals Bureau (searched September 10, 2002).
IUCLID. 2002b. IUCLID data set: n-Butyltin trichloride. International Uniform Chemical Information Database, European Chemicals Bureau (searched September 10, 2002).

Lytle, T.F., C.S. Manning, W.W. Walker, J.S. Lytle and D.S. Page. 2003. Life-cycle toxicity of dibutyltin to the sheepshead minnow (Cyprinodon variegatus) and implications of the ubiquitous tributyltin impurity in test material. Appl. Organometal. Chem. 17: 653–661.

Maguire, R.J. 1992. Supporting document -- environmental section. CEPA assessment of non-pesticidal organotin compounds. National Water Research Institute, Environment Canada, Burlington, Ontario. 239 pp. (Report 92-145).

Maguire, R.J. 2000. Review of the persistence, bioaccumulation and toxicity of tributyltin (TBT) in aquatic environments in relation to Canada's Toxic Substances Management Policy. Water Qual. Res. J. Can. 35: 633–679.

Mamelona, J. and E. Pelletier. 2003. Butyltins biomagnification from macroalgae to green sea urchin: a field assessment. Appl. Organometal. Chem. 17: 759–766.

Meador, J.P. 2000. Predicting the fate and effects to tributyltin in marine systems. Rev. Environ. Contam. Toxicol. 166: 1–48.

Nagase, H., T. Hamasaki, T. Sato, H. Kito, Y. Yoshioka and Y. Ose. 1991. Structure–activity relationships for organotin compounds on the red killifish, Oryzias latipes. Appl. Organometal. Chem. 5: 91–97.

Pest Management Regulatory Agency. 2000. Special review of organotin antifouling paints for ship hulls. Pest Management Regulatory Agency, Health Canada, Ottawa, Ontario. 5 pp. (Special Review Announcement 2000-01, May 9, 2000) [cited in Maguire, 2000].

Rapsomanikis, S., O.F.X. Donard and J.H. Weber. 1987. Methylation of tin (II) and lead (II) in sediments by carbanion donors. Appl. Organometal. Chem. 1: 115–118 [cited in Maguire, 1992].

Rouleau, C., C. Gobeil and H. Tjalve. 1998. Pharmacokinetics and distribution of dietary tributyltin compared to those of methylmercury in the American plaice Hippoglossoides platessoides. Mar. Ecol. Prog. Ser. 171: 275–284.

Schering AG. 1998. Acute immobilization test of mono-n-octyltin trichloride with Daphnia magna. Schering AG, Berlin, Germany. (Research Report No. IC16).

Shim, W.J., J.R. Oh, N.S. Kim and S.H. Lee. 1999. Contamination of butyl- and phenyltin compounds in sediment from shipyards in Korea. In: Proceedings of special session held at Oceans ‘99 on Treatment of Regulated Discharges from Shipyards and Drydocks, Seattle, Washington. The Marine Technology Society, Washington, D.C. pp. 129–144.

Shimasaki, Y., T. Kitano, Y. Oshima, S. Inoue, N. Imada and T. Honjo. 2003. Tributyltin causes masculinization in fish. Environ. Toxicol. Chem. 22: 141–144.

Steinhauser, K.G., W. Amann, A. Spath and A. Polenz. 1985. Investigations on the aquatic toxicity of organotin compounds. Vom Wasser 65: 203–214.

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Weber, J.H. and J.J. Alberts. 1990. Methylation of Sn (IV) by hydroponically incubated Spartina alternifolia. Environ. Technol. 11: 3–8 [cited in Government of Canada, 1993].

Annex 1: Organotin Substances on the Domestic Substances List
Chemical name Molecular formula CAS No.
Monomethyltin compounds
Stannane, trichloromethyl- CH3Cl3Sn 993-16-8
Distannathiane, dimethyldithioxo- C2H6S3Sn2 33397-79-4
Stannane, tris(dodecylthio)methyl- C37H78S3Sn 52165-03-4
Propanoic acid, 3,3,3-[(methylstannylidyne)tris(thio)]tris-, triisooctyl ester C34H66O6S3Sn 53040-42-9
Acetic acid, 2,2,2-[(methylstannylidyne)tris(thio)]tris-, triisooctyl ester C31H60O6S3Sn 54849-38-6
8-Oxa-3,5-dithia-4-stannatetradecanoic acid, 10-ethyl-4-[[2-[(2-ethylhexyl)oxy]-2-oxoethyl]thio]-4-methyl-7-oxo-, 2-ethylhexyl ester C31H60O6S3Sn 57583-34-3
Octanoic acid, (methylstannylidyne)tris(thio-2,1-ethanediyl)ester C31H60O6S3Sn 57813-62-4
9-Octadecenoic acid (Z)-, (methylstannylidyne)tris(thio-2,1-ethanediyl) ester C61H114O6S3Sn 59118-79-5
Dodecanoic acid, (methylstannylidyne)tris(thio-2,1-ethanediyl) ester C43H84O6S3Sn 67859-62-5
Tetradecanoic acid, (methylstannylidyne)tris(thio-2,1-ethanediyl) ester C49H96O6S3Sn 68928-38-1
9,12-Octadecadienoic acid (Z,Z)-, (methylstannylidyne)tris(thio-2,1-ethanediyl) ester C61H108O6S3Sn 68928-40-5
Hexadecanoic acid, (methylstannylidyne)tris(thio-2,1-ethanediyl) ester C55H108O6S3Sn 68928-41-6
Decanoic acid, (methylstannylidyne)tris(thio-2,1-ethanediyl)ester C37H72O6S3Sn 68928-50-7
Dimethyltin compounds
Stannane, dichlorodimethyl- C2H6Cl2Sn 753-73-1
Stannane, dimethylthioxo- C2H6SSn 13269-74-4
Acetic acid, 2,2-[(dimethylstannylene)bis(thio)]bis-, diisooctyl ester C22H44O4S2Sn 26636-01-1
Propanoic acid, 3,3-[(dimethylstannylene)bis(thio)]bis-, diisooctyl ester C24H48O4S2Sn 42378-34-7
Distannoxane, 1,1,3,3-tetramethyl-1,3-bis[(1-oxo-9-octadecenyl)oxy]-, (Z,Z)- C40H78O5Sn2 43136-18-1
Stannane, bis(dodecylthio)dimethyl- C26H56S2Sn 51287-84-4
10-Oxa-4,6-dithia-5-stannahexadecanoic acid, 12-ethyl-5,5-dimethyl-9-oxo-, 2-ethylhexyl ester C24H48O4S2Sn 57057-50-8
8-Oxa-3,5-dithia-4-stannatetradecanoic acid, 10-ethyl-4,4-dimethyl-7-oxo-, 2-ethylhexyl ester C22H44O4S2Sn 57583-35-4
Octanoic acid, (dimethylstannylene)bis(thio-2,1-ethanediyl)ester C22H44O4S2Sn 57813-60-2
9-Octadecenoic acid (Z)-, (dimethylstannylene)bis(thio-2,1-ethanediyl) ester C42H80O4S2Sn 67859-63-6
9,12-Octadecadienoic acid (Z,Z)-, (dimethylstannylene)bis(thio-2,1-ethanediyl) ester C42H76O4S2Sn 67859-64-7
Decanoic acid, (dimethylstannylene)bis(thio-2,1-ethanediyl)ester C26H52O4S2Sn 67874-41-3
Dodecanoic acid, (dimethylstannylene)bis(thio-2,1-ethanediyl) ester C30H60O4S2Sn 68928-42-7
Tetradecanoic acid, (dimethylstannylene)bis(thio-2,1-ethanediyl) ester C34H68O4S2Sn 68928-48-3
Stannane, dimethylbis[(1-oxoneodecyl)oxy]- C22H44O4Sn 68928-76-7
Monobutyltin compounds
Stannane, butyltrichloro- C4H9Cl3Sn 1118-46-3
Stannane, butylhydroxyoxo- C4H10O2Sn 2273-43-0
Stannane, butylchlorodihydroxy- C4H11ClO2Sn 13355-96-9
Distannathiane, dibutyldithioxo- C8H18S3Sn2 15666-29-2
Stannane, butyltris[(2-ethyl-1-oxohexyl)oxy]- C28H54O6Sn 23850-94-4
Acetic acid, 2,2,2-[(butylstannylidyne)tris(thio)]tris-, triisooctyl ester C34H66O6S3Sn 25852-70-4
Stannane, butylmercaptooxo- C4H10OSSn 26410-42-4
Acetic acid, [(butylthioxostannyl)thio]-, 2-ethylhexyl ester C14H28O2S2Sn 26821-65-8
8-Oxa-3,5-dithia-4-stannatetradecanoic acid, 4-butyl-10-ethyl-4-[[2-[(2-ethylhexyl)oxy]-2-oxoethyl]thio]-7-oxo-, 2-ethylhexyl ester C34H66O6S3Sn 26864-37-9
Propanoic acid, 3,3,3-[(butylstannylidyne)tris(thio)]tris-, triisooctyl ester C37H72O6S3Sn 36118-60-2
Octanoic acid, (butylstannylidyne)tris(thio-2,1-ethanediyl)ester C34H66O6S3Sn 59118-80-8
9-Octadecenoic acid (Z)-, (butylstannylidyne)tris(thio-2,1-ethanediyl) ester C64H120O6S3Sn 67361-76-6
Decanoic acid, (butylstannylidyne)tris(thio-2,1-ethanediyl)ester C40H78O6S3Sn 67874-51-5
Tetradecanoic acid, (butylstannylidyne)tris(thio-2,1-ethanediyl) ester C52H102O6S3Sn 68928-34-7
9,12-Octadecadienoic acid (Z,Z)-, (butylstannylidyne)tris(thio-2,1-ethanediyl) ester C64H114O6S3Sn 68928-37-0
Hexadecanoic acid, (butylstannylidyne)tris(thio-2,1-ethanediyl) ester C58H114O6S3Sn 68928-39-2
Dodecanoic acid, (butylstannylidyne)tris(thio-2,1-ethanediyl) ester C46H90O6S3Sn 68928-52-9
Ethanol, 2,2,2-[(butylstannylidyne)tris(thio)]tris- C10H24O3S3Sn 70729-71-4
Dibutyltin compounds
Stannane, dibutylbis[(1-oxododecyl)oxy]- C32H64O4Sn 77-58-7
1,3,2-Dioxastannepin-4,7-dione, 2,2-dibutyl- C12H20O4Sn 78-04-6
6H-1,3,2-Oxathiastannin-6-one, 2,2-dibutyldihydro- C11H22O2SSn 78-06-8
Stannane, dibutyldichloro- C8H18Cl2Sn 683-18-1
Stannane, dibutyloxo- C8H18OSn 818-08-6
Stannane, bis(acetyloxy)dibutyl- C12H24O4Sn 1067-33-0
Stannane, dibutylbis(dodecylthio)- C32H68S2Sn 1185-81-5
Stannane, dibutylbis[(2-ethyl-1-oxohexyl)oxy]- C24H48O4Sn 2781-10-4
Distannoxane, 1,1,3,3-tetrabutyl-1,3-bis[(1-oxododecyl)oxy]- C40H82O5Sn2 3669-02-1
Stannane, dibutylthioxo- C8H18SSn 4253-22-9
Stannane, dibutylbis[(1-oxooctadecyl)oxy]- C44H88O4Sn 5847-55-2
8-Oxa-3,5-dithia-4-stannatetradecanoic acid, 4,4-dibutyl-10-ethyl-7-oxo-, 2-ethylhexyl ester C28H56O4S2Sn 10584-98-2
Stannane, dibutylbis[(1-oxo-9-octadecenyl)oxy]-, (Z,Z)- C44H84O4Sn 13323-62-1
Stannane, butoxydibutylchloro- C12H27ClOSn 14254-22-9
2,7,9-Trioxa-8-stannatrideca-4,11-dien-13-oic acid, 8,8-dibutyl-3,6,10-trioxo-, methyl ester, (Z,Z)- C18H28O8Sn 15546-11-9
5,7,12-Trioxa-6-stannaoctadeca-2,9-dienoic acid, 6,6-dibutyl-14-ethyl-4,8,11-trioxo-, 2-ethylhexyl ester C32H56O8Sn 15546-12-0
5,7,12-Trioxa-6-stannahexadeca-2,9-dienoic acid, 6,6-dibutyl-4,8,11-trioxo-, butyl ester, (Z,Z)- C24H40O8Sn 15546-16-4
Tin, dibutylbis(2,4-pentanedionato-o,o )-, (oc-6-11)- C18H32O4Sn 22673-19-4
2-Butenoic acid, 4,4-[(dibutylstannylene)bis(oxy)]bis[4-oxo-, diisooctyl ester, (Z,Z)- C32H56O8Sn 25168-21-2
Stannane, dibutylbis[(1-oxoneodecyl)oxy]- C28H56O4Sn 25168-22-3
Acetic acid, 2,2-[(dibutylstannylene)bis(thio)]bis-, diisooctyl ester C28H56O4S2Sn 25168-24-5
Propanoic acid, 3,3-[(dibutylstannylene)bis(thio)]bis-, diisooctyl ester C30H60O4S2Sn 26761-46-6
Dodecanoic acid, (dibutylstannylene)bis(thio-2,1-ethanediyl)ester C36H72O4S2Sn 28570-24-3
5,7,12-Trioxa-6-stannatetracosa-2,9-dienoic acid, 6,6-dibutyl-4,8,11-trioxo-, dodecyl ester, (Z,Z)- C40H72O8Sn 33466-31-8
Distannoxane, 1,1,3,3-tetrabutyl-1,3-bis[(2-ethyl-1-oxohexyl)oxy]- C32H66O5Sn2 45314-70-3
10-Oxa-4,6-dithia-5-stannahexadecanoic acid, 5,5-dibutyl-12-ethyl-9-oxo-, 2-ethylhexyl ester C30H60O4S2Sn 53202-61-2
5,7,12-Trioxa-6-stannahexacosa-2,9-dienoic acid, 6,6-dibutyl-4,8,11-trioxo-, tetradecyl ester, (Z,Z)- C44H80O8Sn 60659-60-1
5,7,12-Trioxa-6-stannatriaconta-2,9-dienoic acid, 6,6-dibutyl-4,8,11-trioxo-, octadecyl ester, (Z,Z)- C52H96O8Sn 61813-52-3
9-Octadecenoic acid (Z)-, (dibutylstannylene)bis(thio-2,1-ethanediyl) ester C48H92O4S2Sn 67361-77-7
9,12-Octadecadienoic acid (Z,Z)-, (dibutylstannylene)bis(thio-2,1-ethanediyl) ester C48H88O4S2Sn 67859-61-4
Tetradecanoic acid, (dibutylstannylene)bis(thio-2,1-ethanediyl) ester C40H80O4S2Sn 67859-65-8
Tin, dibutyl[N-(carboxymethyl)-N-(2-hydroxyethyl)glycinato(2-)]- C14H27NO5Sn 68239-46-3
Hexadecanoic acid, (dibutylstannylene)bis(thio-2,1-ethanediyl) ester C44H88O4S2Sn 68298-42-0
2-Butenoic acid, 4,4-[(dibutylstannylene)bis(oxy)]bis[4-oxo-, diisopentadecyl ester, (Z)- C46H84O8Sn 68299-23-0
Decanoic acid, (dibutylstannylene)bis(thio-2,1-ethanediyl) ester C32H64O4S2Sn 68928-47-2
Propanoic acid, 3,3-[(dibutylstannylene)bis(thio)]bis-, diisotridecyl ester C40H80O4S2Sn 84896-44-6
3,5,7,9-Tetraoxa-4,8-disila-6-stannaundecane, 6,6-dibutyl-4,4,8,8-tetraethoxy- C210H48O8Si2Sn 87735-26-0
Dibutyltin bis(stearyl maleate) 166432-49-1
Tributyltin compounds
Distannoxane, hexabutyl- C24H54OSn2 56-35-9
Stannane, tributyl- C12H28Sn 688-73-3
Stannane, tributylchloro- C12H27ClSn 1461-22-9
Stannane, tributylfluoro- C12H27FSn 1983-10-4
Stannane, tributyl[(2-methyl-1-oxo-2-propenyl)oxy]- C16H32O2Sn 2155-70-6
2-Butenoic acid, 4-oxo-4-[(tributylstannyl)oxy]-, (2Z)- C16H30O4Sn 4027-18-3
Phenol, 2-[[(tributylstannyl)oxy]carbonyl]- C19H32O3Sn 4342-30-7
Stannane, [(2-octyl-1,4-dioxo-1,4-butanediyl)bis(oxy)]bis[tributyl- C36H74O4Sn2 67701-37-5
Monooctyltin compounds
Acetic acid, 2,2,2-[(octylstannylidyne)tris(thio)]tris-, triisooctyl ester C38H74O6S3Sn 26401-86-5
8-Oxa-3,5-dithia-4-stannatetradecanoic acid, 10-ethyl-4-[[2-[(2-ethylhexyl)oxy]-2-oxoethyl]thio]-4-octyl-7-oxo-, 2-ethylhexyl ester C38H74O6S3Sn 27107-89-7
Dioctyltin compounds
Stannane, dioctylbis[(1-oxododecyl)oxy]- C40H80O4Sn 3648-18-8
5,7,12-Trioxa-6-stannaoctadeca-2,9-dienoic acid, 14-ethyl-6,6-dioctyl-4,8,11-trioxo-, 2-ethylhexyl ester C40H72O8Sn 10039-33-5
8-Oxa-3,5-dithia-4-stannatetradecanoic acid, 10-ethyl-4,4-dioctyl-7-oxo-, 2-ethylhexyl ester C36H72O4S2Sn 15571-58-1
1,3,2-Dioxastannepin-4,7-dione, 2,2-dioctyl- C20H36O4Sn 16091-18-2
Stannane, bis(dodecylthio)dioctyl- C40H84S2Sn 22205-30-7
Acetic acid, 2,2-[(dioctylstannylene)bis(thio)]bis-, diisooctyl ester C36H72O4S2Sn 26401-97-8
Stannane, dioctylbis[(1-oxoneodecyl)oxy]- C36H72O4Sn 68299-15-0
5,7,12-Trioxa-6-stannaeicosa-2,9-dienoic acid, 13-methyl-6,6-dioctyl-4,8,11-trioxo-, 1-methyloctyl ester, (Z,Z)- C42H76O8Sn 108537-06-0
Triphenyltin compounds
Stannane, fluorotriphenyl- C18H15FSn 379-52-2
Tetraphenyltin compounds
Stannane, tetraphenyl- C24H20Sn 595-90-4
Other organotin compounds
Distannoxane, hexakis(2-methyl-2-phenylpropyl)- C60H78OSn2 13356-08-6
Acetic acid, 2,2,2-[(1,1,3-tributyl-1-distannathianyl-3-ylidene)tris(thio)]tris-, triisooctyl ester C42H84O6S4Sn2 33703-04-7
Propanoic acid, 3,3-[bis[[2-(isooctyloxy)-2-oxoethyl]thio]stannylene]bis-, dibutyl ester C34H64O8S2Sn 63397-60-4
9-Octadecenoic acid (Z)-, 2-mercaptoethyl ester, reaction products with dichlorodimethylstannane, sodium sulfide (Na2S) and trichloromethylstannane 68442-12-6
Stannane, dibutylbis[(1-oxopentadecyl)oxy]-, branched 68512-27-6

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