Return
to Index Page
Return to Abstracts
Activity:
Antifoulant,
Fungicide, Microbiocide (Organotin)
Structure:
Adverse
Effects:
Brain
Developmental / Reproductive
Diabetes
Eye
Endocrine: Suspected Disruptor
Environmental
A
little history...
In the early 1960s, both tributyltin
oxide (TBTO) and TBT fluoride were
tested, mainly in Africa, as molluscicides against
several freshwater snail species that are vectors of the
disease schistosomiasis, the snails being the intermediate
hosts of the trematode parasite. This
use led to the introduction of TBT,
during the mid 1960s, as an antifouling paint on
boats. At the same time TBT compounds were being registered
as wood preservatives (the first registration was in 1958).
Ref:
Tributyltin Compounds. Environmental Health Criteria 116.
International Programme on Chemical Safety. http://www.inchem.org/documents/ehc/ehc/ehc116.htm
Table
5-1. Current U.S. Manufacturers of Selected Tin Compounds
ATOFINA
Chemicals, Inc. Specialty Chemicals Division Carrollton, Kentucky
Derived from SRI 2003. SRI reports production of chemicals
produced in commercial quantities (defined as exceeding 5,000
pounds or $10,000 in value annually) by the companies listed.
Ref: DRAFT TOXICOLOGICAL PROFILE FOR TIN AND COMPOUNDS. U.S.
DEPARTMENT OF HEALTH AND HUMAN SERVICES. Public Health Service
Agency for Toxic Substances and Disease Registry. September
2003.
http://www.atsdr.cdc.gov/toxprofiles/tp55.pdf
|
Table
14. Acute toxicity of tributyltin [TBT] to RAT
Ref:
Tributyltin Compounds. Environmental Health Criteria 116. International
Programme on Chemical Safety. http://www.inchem.org/documents/ehc/ehc/ehc116.htm
|
TBT |
Route |
Observation
period (days) |
LD50
(mg/kg body weight) |
Reference |
oxide |
oral |
7 |
194
(165-227)b |
Elsea
& Paynter (1958) |
oxide |
oral |
7 |
148 (113-195)c |
Elsea
& Paynter (1958) |
oxide |
oral |
7 |
180 (132-228) |
Truhaut
et al. (1976) |
oxide |
oral |
21 |
197
(137-273) |
Funahashi
et al. (1980) |
oxide |
oral |
|
127 |
Schweinfurth (1985) |
oxide |
ip |
14 |
20
(18-21) |
Poitou
et al. (1978) |
oxide |
oral |
|
234 |
Sheldon
(1975) |
fluoride |
oral |
|
200 |
Sheldon
(1975) |
fluoride |
oral |
14 |
94 |
Schweinfurth (1985) |
chloride |
oral |
14 |
122 |
Schweinfurth (1985) |
acetate |
oral |
|
113.5 |
Klimmer
(1969) |
benzoate |
oral |
|
141 |
Klimmer
(1969) |
benzoate |
oral |
14 |
99/203
|
Schweinfurth (1985) |
oleate |
oral |
|
225 |
Klimmer
(1969) |
linoleate |
oral |
14 |
190 |
Schweinfurth
(1985) |
abietate |
oral |
14 |
158 |
Schweinfurth (1985) |
naphthenate |
oral |
14 |
224 |
Schweinfurth (1985) |
b Application
as aqueous suspension.
c Application in corn oil.
|
From
Science Direct
Marine
Chemistry; Volume 85, Issues 3-4 , March 2004,
Pages 157-167
Speciation of trialkyltin(IV) cations in natural fluids
Claudia
Foti (a), Antonio Gianguzza (b), Demetrio Milea (a), Frank
J. Millero (c) and Silvio Sammartano (a)
a Dipartimento
di Chimica Inorganica, Chimica Analitica e Chimica Fisica,
Università di Messina, Salita Sperone 31, Vill. S.
Agata di Messina, 98166, Messina, Italy
b Dipartimento di Chimica Inorganica e Chimica Analitica
"Stanislao Cannizzaro", Università di Palermo,
Viale delle Scienze, Parco d'Orleans, 90128, Palermo, Italy
c Rosenstiel School of Marine and Atmospheric Science, University
of Miami, 4600 Rickenbacker Causeway, Miami, FL 33149, USA
The
hydrolysis of (CH3)3Sn+, (C2H5)3Sn+ and (C3H7)3Sn+ has been
studied in a Synthetic Seawater (SSW) ionic medium simulating
the major composition of natural seawater, at different
salinities (5≤S≤45), and at t=25 °C. Interactions
with anionic components of SSW, considered as single sea
salt, are determined by means of a complex formation model.
By potentiometric measurements (ISE-H+ and ISE-F- electrodes),
the model has been extended to also consider interactions
of organotins with carbonate and fluoride ions, which are
other important components of seawater. Literature and new
values of hydrolysis constants in different ionic media
(NaNO3, NaCl, Na2SO4 and SSW) are used to determine Pitzer
interaction parameters. Predictive equations for the calculation
of unknown hydrolysis constants and Pitzer interaction parameters
of other trialkyltin(IV) cations, such as tributyltin(IV),
are proposed.
Excerpts:
...
Concentrations of fluoride and bicarbonate+carbonate anions
are much lower than those of other macro-components of seawater
(0.7 and 2.7 mmol l-1 for fluoride and bicarbonate+carbonate,
respectively, in seawater, S=35), such as chloride and sulfate,
but their complexes are often stronger. Moreover,
since carbonates and fluorides play a very important role
in many geo-chemical and bio-chemical processes in seawater,
their contribution to the speciation studies of organotin
compounds in that medium cannot be neglected. ...
3.4.
Interactions with carbonate and fluoride
In spite of the amount of literature data concerning the
interactions of fluoride and carbonate ligands with most
of the metal ions, no data are reported on their interactions
with organotin(IV) cations. In order to give a complete
picture of trialkyltin(IV) cations speciation in natural
fluids, we studied interactions of (CH3)3Sn+ with fluoride
and carbonate. First, it was necessary to determine the
protonation constants of fluoride and carbonate anions.
Results are reported in Table 4, in the ionic strength range
0<I≤1.0 mol l-1 (for NaCl) and at t=25 °C.
As can be seen, in the fluoride system, the formation constant
of the binuclear species HF2- is also reported.
Potentiometric
data (ISE-H+ and ISE-F- electrodes) of (CH3)3Sn+ cation
in the presence of NaF and Na2CO3 salts, indicate the formation
of (CH3)3SnF0, (CH3)3Sn(OH)F-, and (CH3)3Sn(OH)CO32- species.
These formation constants are reported in Table 5 and Table
6, at different ionic strengths in NaCl or NaNO3 at t=25
°C. As expected, the stability
of fluoride species is greater than the chloride species
[(CH3)3SnCl0: log K=-0.6, at I=0 mol l-1] (Fig. 3a). The
formation of the (CH3)3SnF0 species is dominant, whilst,
the mixed (CH3)3Sn(OH)F- species is negligible. The mixed
(CH3)3Sn(OH)CO32- species is formed in significant percentages
over pH=9, as can be seen in Fig. 4a for the speciation
diagram of (CH3)3Sn+ vs. pH.
|
Brain
(click
on for all fluorinated pesticides)
... In
rats given a single oral dose of 40 mg/kg tributyltin fluoride
(15 mg Sn/kg), transient elevations in tributyltin, dibutyltin,
monobutyltin, and inorganic tin were observed in brain and liver
over the 8-day period following the dose, indicating that dealkylation
had occurred (Iwai et al. 1981, see Section 3.4.3). ..
Ref: DRAFT TOXICOLOGICAL PROFILE FOR TIN
AND COMPOUNDS. U.S. DEPARTMENT OF HEALTH AND HUMAN SERVICES. Public
Health Service Agency for Toxic Substances and Disease Registry.
September 2003.
http://www.atsdr.cdc.gov/toxprofiles/tp55.pdf
• Defintion:
Dealkylation: The
removing of alkyl groups from a compound.
Developmental
/
Reproductive
(click on for all fluorinated pesticides)
-- Lee and Xu
(1984) reported that exposure to 25 mgl TPT acetate or TPTF
caused 46-47% reduction in 1-methyladenine induced germnal vesicle
breakdown for oocytes of the starfish Patiro pectinefera.
Having recorded such an effect on mitosis, it is postulated that
fertilization and developmental effects would be induced in this
species (page 46)
-- Cotta-Ramusino and Doci (1987) conducted tests using TPT acetate
to assess the sensitivity of some aquatic organisms. The least
senstive of those tested was Asellus aquaticus, which gave
a 48 h TLm of 1100 ugl. In contrast to this, Linden et al (1979)
found that the harpacticoid Nitrocra spinipes was very
sensitive to TPT. The authors established
a 96 hr LC50 of 8 ugl TPTF (page 55).
Ref:
Evaluation on: A Review of the Environmental Effects of Triorganotin
Compounds. October 1994. Issue No. 111. Prepared by: The Health
and Safety Executive, Biocides & Pesticides Assessment Unit.
Available from: Department for Environment, Food and Rural Affairs,
Pesticides Safety Directorate, Mallard House, Kings Pool, 3 Peasholme
Greene, York YO1 7PX.
Available online at http://www.pesticides.gov.uk/citizen/evaluations/evallist_alphabet.htm
•
Excellent "Mitosis animation" available at (scroll
down):
http://www.biology.arizona.edu/cell_bio/tutorials/cell_cycle/cells3.html
Diabetes
(click
on for all fluorinated pesticides)
Pub Med abstract:
... These
results suggest that hyperlipidemia induced in rabbits by tributyltin
fluoride is due to decreased LPL [Lipoprotein lipase] activity.
The decrease in LPL activity seems to be related to the inhibition
of insulin release from islets by TBTF.
Ref: [Properties
and mechanism of hyperlipidemia induced in rabbits by tributyltin
fluoride] by Matsui H, Wada O, Manabe S, Ono T, Iwai H, Fujikura
T. Sangyo Igaku 1982 Mar;24(2):163-71.
•
Hyperlipidemia = High Cholesterol
Endocrine:
Suspected Disruptor
(click
on for all fluorinated pesticides)
Table
9 Organotin compounds suspected of being endocrine disruptors. |
Common
name |
CAS-no. |
Y
/µg l Š1 |
log
P ow |
Bis(tributyltin)oxide |
56-35-9 |
8000
Š10 000 |
3.62 |
Triphenyltinhydroxide |
76-87-9 |
400 |
- |
Tributyltin
fluoride |
1983-10-4 |
- |
- |
Ysat
:Water solubility in seawater at 22 ”C.
P ow :Partition coefficient octanol/water. |
Ref:
Endocrine Disruptors in the Environment (IUPAC Technical
Report). Prepared for publication by J.LINTELMANN et al. INTERNATIONAL
UNION OF PURE AND APPLIED CHEMISTRY. Pure Appl.Chem.,Vol.75,No.5,pp.631
Š681,2003. ©2003 IUPAC.
Full report available at
http://www.iupac.org/publications/pac/2003/pdf/7505x0631.pdf
|
Suspected
Endocrine Disruptor
Ref: June 14, 2001 - Implementation of the
Community Strategy for Endocrine Disruptors - a range of substances
suspected of interfering with the hormone systems of humans and
wildlife. Communication from the Commission to the Council and
the European Parliament. Commission of the European Communities,
Brussels COM (2001) 262 final.
http://www.fluoridealert.org/pesticides/Endocrine.Disruptors.EC2001.pdf
-
More information available at:
http://europa.eu.int/eur-lex/en/com/cnc/2001/com2001_0262en01.pdf
Eye
(click
on for all fluorinated pesticides)
Abstract: The acute
and chronic toxicities of anti fouling coatings were studied in
animals. The acute oral median lethal dose (LD50) was determined
for bis(tri-n-butyltin)oxide (56359), tributyltin-fluoride
(1983104) and triphenyltin-fluoride
(379522) for rats and rabbits... All were
severe or extreme eye irritants and most were moderate to severe
skin irritants.
Ref: 1975
Journal of Paint Technology, Vol. 47, No. 600, pages 54-58. Effects
Of Organotin Anti-Fouling Coatings On Man And His Environment
by Sheldon AW.
http://toxnet.nlm.nih.gov/cgi-bin/sis/search/f?./temp/~AAAjCaaO4:1
Environmental
(click
on for all fluorinated pesticides)
Tributyltin
fluoride: Acute Aquatic Ecotoxicity Summaries for Tributyltin
fluoride on All Taxa Groups.
Ref: PAN Pesticides Database - Chemical
Toxicity Studies on Aquatic Organisms.
http://www.pesticideinfo.org/List_AquireAcuteSum.jsp?CAS_No=1983-10-4&Rec_Id=PC34614
|
Common
Name |
Scientific
Name |
Avg Species LC50 (ug/L) |
LC50
Std Dev |
Number
of Studies |
Avg
Species Rating |
Amphibians
|
Frog |
Rana
temporaria |
30.0 |
- |
1 |
Very
Highly Toxic |
Crustaceans
|
Fiddler
crab |
Uca pugilator |
800.0 |
- |
1 |
Highly
Toxic |
Fish |
Channel
catfish |
Ictalurus punctatus |
8.15 |
3.85 |
2 |
Very
Highly Toxic |
Bluegill |
Lepomis macrochirus |
7.35 |
3.65 |
2 |
Very
Highly Toxic |
Rainbow
trout,donaldson trout |
Oncorhynchus
mykiss |
11.2 |
7.80 |
1 |
Very
Highly Toxic |
Shell
thickening. Alzieu et al. (1982) reported that adult oysters
(Crassostrea gigas) developed gel
centres in the shell when they were exposed to TBT
fluoride at a concentration of 0.2 µg/litre.
Ref: C Alziieu et al. (1982).
Influence des peintures antisalissures base d'organostanniques
sur la calcification de la coquille de l'huitre Crassostrea
gigas. Rev. Trav. Inst. Pches Marit., 45: 101-116.
Ref: Tributyltin
Compounds. Environmental Health Criteria 116. International
Programme on Chemical Safety.
http://www.inchem.org/documents/ehc/ehc/ehc116.htm
Aquatic
acute toxicity values for tributyltin fluoride include a
bleak fish 96-hour LC 50 of 2.3 ppb,
an algae 72-hour EC50 of 9.3 ppb, and a Harpacticoid
copepod 96-hour LC 50 of 0.8
ppb. EPA believes that there is sufficient evidence
for listing tributyltin fluoride on EPCRA section 313 pursuant
to EPCRA section 313(d)(2)(C) based on the available environmental
toxicity data.
Ref: USEPA/OPP. Support
Document for the Addition of Chemicals from Federal Insecticide,
Fungicide, Rodenticide Act (FIFRA) Active Ingredients to
EPCRA Section 313. U. S. Environmental Protection Agency,
Washington, DC (1993). As cited by US EPA in: Federal
Register: January 12, 1994. Part IV. 40 CFR Part 372.
Addition of Certain Chemicals; Toxic Chemical Release Reporting;
Community Right-to-Know; Proposed Rule
Tributyltin
Compounds. The acute toxicity of tributyltin compounds has
been studied on several species of freshwater fish. LC50s
range from 6 to 240 ugl TBT. The most
sensitive species was the cyprinid Alburnus alburnus
with a 96 hr LC50 of 6-8 ugl TBTF. When the same species
was tested against TBTO, a 96 hr LC50 of 15 ugl was reported
(Linden et al. 1979). - page 57.
In
soils, risk of TBT contamination comes essentially from
TBTO and TBTF and their use
as wood preservatives. - page 4.
Acute
toxicity. Tributyltin Compounds ... Adult bivalves are more
resistant to short term exposure to TBT than long term exposure,
since they can isolate themselves from their environment
by closing their valves. For example, the pacific oyster
showed tolerance of short term exposure to high concentrations
of TBT (96hr LC50 290 ugl) yet this same species showed
30% mortality after 113 days exposure to 0.2 ugl TBT and
100% mortality after both 30 days exposure to 2.0 ugl TBT
and 35 days exposure to 0.5 ugl TBTF
(Thain, 1983; Heral et al. 1983; Alzieu et al. 1981) - ...
Histopathological studies on adult pacific oysters (Crassostrea
gigas) have revealed that the digestive gland is the primary
target organ for TBT toxicity (Chagot et al. 1990). These
studies revealed that histological modification of cells
occurred in pacific oysters for 2 weeks to concentrations
as low as 0.002 ugl TBTF. Such
modifications were reversible within 6 days during depuration.
However, pacific oysters exposed for 2
weeks to 0.131 ugl TBTF showed
more severe cell damage (limited necrosis) and no recovery
was observed in gill epithelium 21 days after exposure (Chagot
et al. 1990)... - pages 26-27.
6.2.2.4
Shell thickening. Tributyltin Compounds. ... Chagot et al
(1990) reported anomalies in shell
calcification for 13% of adult pacific oysters exposed to
0.002 ugl TBTF or less, and it was concluded that
0.002 ugl TBT was the threshold limit for induction of chambers
in the shells of such oysters. 47%
of pacific oysters exposed to 0.065 ugl TBTF showed shell
chamber formation. It was observed that such shell
chamber formation did not occur during the 18 day accumulation
(exposure period) phase but during the 21 day depuration
phase (Chagot et al. 1990)... - page 35.
Ref:
Evaluation on: A Review of the Environmental Effects of
Triorganotin Compounds. October 1994. Issue No. 111. Prepared
by: The Health and Safety Executive, Biocides & Pesticides
Assessment Unit. Available from: Department for Environment,
Food and Rural Affairs, Pesticides Safety Directorate, Mallard
House, Kings Pool, 3 Peasholme Greene, York YO1 7PX.
Available online at http://www.pesticides.gov.uk/citizen/evaluations/evallist_alphabet.htm
|
|