Environ. Sci. Technol. 2000, 34, 2697-2702
Speciation of Organotin Compounds,
Total Tin, and Major Trace Metal
Elements in Poisoned Human
Organs by Gas
Chromatography-Flame Photometric
Detector and Inductively Coupled
Plasma-Mass Spectrometry
JIANG GUI-BIN,* ZHOU QUN-FANG, AND
HE BIN
Research Center for Eco-Environmental Sciences, Chinese
Academy of Sciences, P.O. Box 2871, Beijing, 100085, China
The organ samples from a victim who died of organotin
contaminated lard were studied by the technique which
involved gas chromatography-flame photometric detector (GCFPD) and inductively coupled plasma-mass spectrometry
(ICP-MS). Organotin compounds were determined by the
following steps: (1) digestion with 1 M CuSO4 and KBr-H2SO4 solutions; (2) extraction with 0.1% tropolonecyclohexane; (3) derivatization with a n-pentyl Grignard
reagent; (4) purification with florisil; and (5) analysis by GCFPD. Experimental results showed that the victim’s
organs including the heart, the kidney, the liver, and the
stomach contained extremely high levels of methyltin
compounds and some amounts of inorganic tin, while the
blank organs only contained nearly equal amounts of
inorganic tin. The contents of all organotin compounds
with methyltri(n-propyl)tin (MeSnPr3) acting as an internal
standard were detected by GC-FPD and found between
the levels of 0.10 and 1.93 µg/g (wet weight). The amounts
of total tin ranged from 0.84 to 5.02 µg/g, and several
major trace metal elements were measured by ICP-MS.
To our knowledge, this is the first case of methyltin species
found in human organs.
Introduction
Organotin derivatives are by far more toxic than its inorganic
forms, and the toxic properties of organotins are related to
the number and nature of organic groups attached to atom
Sn (1). The toxicity of organotins increases with progressive
introduction of organic groups at the tin atom, with maximum
toxicity for trialkylated compounds and decreasing toxicity
with increased length of organic moiety (2, 3). Since tributyltin
(TBT) was found to cause detrimental environmental impacts
in the late 1970s, the use of TBT-containing antifouling paints
is now controlled or banned in many countries. As a result,
the biocidal uses of the trisubstituted organotin compounds
are exceeded by the applications of the di- and monosubstituted derivatives, used as stabilizers and catalysts (4). More
recent estimates assumed that the annual world production
of organotins may reach 50 000 tons (5). The increasing
* Corresponding author fax: 8610-62923563; e-mail: gbjiang@
mail.rcees.ac.cn.
10.1021/es0008822 CCC: $19.00
Published on Web 05/27/2000
 2000 American Chemical Society
annual usage of organotins raises the possibility of environmental pollution.
In the past, one disastrous organotin poisoning was known
as the “Stalinon” affair, which happened in France in 1954
and resulted in the death of ca. 110 people (6). Stalinon was
a proprietary preparation sold in capsules throughout France
for the treatment of furuncles and other staphylococcal skin
infections, osteomyelitis, anthrax, and acne. In Stalinon, the
triethyltin derivative was identified as the toxic contaminant
which resulted in neurological symptoms in many of the
afflicted patients. Since then, occasional organotin poisoning
affairs still occur from careless use in the worldwide scope.
During the 1999 New Year’s days, in eastern China’s Jiangxi
province, Longnan and Dingnan county, a tragedy happened
as a result of the improper management of the toxic organotin
compounds. The edible lard was contaminated with extremely high levels of organotin compounds which poisoned
more than 1000 people; hundreds were hospitalized, and
three of them died.
It is the dependence of the toxicity on the chemical
structure of the compound that makes speciation analysis
so important. Elucidation of the biological effects and
environmental impacts of tin species cannot be achieved by
conventional total tin analysis but requires analytical techniques which allow both the identification and the quantitative determination of the variety of ionic inorganic and
alkyltin. Many papers have reported the analysis of organotin
in biotic samples, for example marine mammals (7), mussel
(8), oyster (9), fish (10), etc. But no one describes the analysis
of organotin poisoned human organs up to date.
In this study, the organs from a victim in the food
poisoning accident and a normal dead body were studied.
Tri-, dimethyltin, and inorganic tin at levels of 0.10-1.93
µg/g were found in the victim’s organs by the method of
Grignard pentylation and subsequently analyzed by using
capillary GC-FPD with quartz surface-induced tin emission,
while in the blank organs only inorganic tin at levels of 0.180.59 µg/g were found. The amounts of total tin ranging from
0.03 to 5.02 µg/g as well as the contents of several major
trace metal elements were detected by ICP-MS.
2. Experimental Section
2.1. Instrumentation. A GC-9A gas chromatograph (Shimadzu, Japan) fitted with a 25-m HP-1 capillary column (0.32
mm i.d.) coated with a 0.17 µm thickness film was used. The
oven temperature was held at 50 °C for 2 min, raised by 10
°C/min to 200 °C, and then held for 5 min with the injector
temperature held at 220 °C constantly throughout the
experiment. Nitrogen (high pure) served as carrier gas; the
column head pressure was controlled at 0.26 mPa.
The detector, with high sensitivity and selectivity for
organotin, was a laboratory-made flame photometric detector
using quartz surface-induced luminescence (QSIL-FPD). Its
configuration and analytical figure of merits were described
previously (11, 12). The detector was operated with a
hydrogen-rich flame; hydrogen and air were controlled at
260 and 90 mL/min. The detector temperature was set at 160
°C, and all measurements were carried out by using a 394
nm interference filter. Chromatograms were recorded on a
SC-1100 data processing system.
A Plasma-Quad 3 (VG Elemental, Winsford, U.K.) ICP-MS
was used for the determination of total tin and several trace
elements. General instrumental operating conditions were
given in Table 1.
2.2. Materials. Trimethyltin chloride (TMT, 98%), dimethyltin dichloride (DMT, 97%), and monomethyltin
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TABLE 1. Experimental Conditions for ICP-MS
forward power
reflected power
coolant argon flow rate
auxiliary gas flow rate
nebulizer gas flow rate
sample uptake rate
sampling depth
mass spectrometer
sampler (nickel) orifice
skimmer (nickel) orifice
first stage pressure
second stage pressure
third stage pressure
date acquisition
mass range
total acquisition time
1350 w
<5 w
14 L/min
0.9 L/min
0.8 L/min
1.0 mL/min
15 mm
1.0 mm
0.7 mm
1.6 × 105 mPa
1.0 × 10 mPa
1.7 × 10-1 mPa
range-scanning mode
m/z 50-210
50 s
trichloride (MMT, 97%) were obtained from Aldrich Chem.
Co. (U.S.A.). Each compound was directly weighed and
dissolved in methanol to form a concentration level of 1
mg/mL (as Sn) as the stock solutions. The solution of Sn(IV)
was prepared by dissolution of Sn in hot concentrated HCl
and subsequently diluted with methanol to an appropriate
volume. Working standard solutions (10 µg/mL) were obtained by diluting the store solutions with deionized water,
and the pH was adjusted to 2 using 12 M HCl to ensure their
stability.
The CuSO4 (1 M) solution was prepared by dissolving 50
g of CuSO4‚5H2O in 200 mL of deionized water, while
dissolving 90 g of KBr and 27.5 mL of concentrated H2SO4
in 200 mL of deionized water can serve as the digestion
solution.
The extraction solution was freshly made just before the
extraction operation by dissolving tropolone (98%, Acros Co.
U.S.A) in cyclohexane to form a concentration of 0.1%.
The Grignard reagents n-pentylmagnesium bromide (nPeMgBr, 2.0 M) and n-propylmagnesium bromide (n-PrMgBr,
2.0 M) were prepared in the laboratory according to the
standard synthetic methods (13).
The internal standard methyltri(n-prothyl)tin (MeSnPr3,
80 ng/mL) was synthesized by reaction of MeSnCl3 (10 µg/
mL, cyclohexane) with 2.0 M n-PrMgBr Grignard reagent.
2.3. Sample Preparation. 2.3.1. Organ Sample Preparation
for GC-FPD Analysis. A sample of a wet organ (from the victim
or the normal dead body) (0.4-0.8 g) was homogenized and
placed in a 10-mL centrifuge tube fitted with a Teflon-lined
cap and mixed with 2 mL of the internal standard MeSnPr3
(80 ng/mL). The sample was digested by 2 mL of KBr-H2SO4
solution and 0.5 mL of CuSO4 (1 M) for 15 min under vigorous
shaking (14). The pH of the mixture was adjusted to 5 by
adding 5.0 mL of citric acid-NaH2PO4 buffer. They were then
extracted with two portions of 2.5 mL of 0.1% tropolonecyclohexane solution under ultrasonic bath for 15 min. After
10 min of centrifugation at 2000r/min, the cyclohexane
extracts could be submitted to a Grignard pentylation step
without further precautions. The presence of traces of water
in these extracts did not interfere with the pentylation of
organotins or Sn(IV) to pentylated compounds, whenever
an excess of (n-Pe)MgBr was added (0.5 mL of a 2.0 M solution
of (n-Pe)MgBr in diethyl ether) (15). The mixture was obtained
after the reaction was stirred for 15 min at room temperature
and subsequently treated with 2 mL of 0.5 M H2SO4 solution
to destroy the excess Grignard reagent, followed by an
additional wash with 60 mL of deionized water. After being
manually and vigorously shaken for 5 min, the solution was
allowed to stand 5 min for phase separation. The organic
layer, containing the compounds of interest, was separated,
and the aqueous phase was then re-extracted with 5 mL of
cyclohexane. The combined organic layers were eventually
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ENVIRONMENTAL SCIENCE & TECHNOLOGY / VOL. 34, NO. 13, 2000
dried with 0.2 mg of anhydrous sodium sulfate and then
purified by Florisil (0.8 mg) which had been packed in a
Pyrex tube and prewashed with cyclohexane. The eluted
solution was gently concentrated by passing through a
nitrogen stream. One microliter volume of solution was then
injected into GC for analysis.
2.3.2. Sample Preparation for ICP-MS Analysis. A portion
of an organ sample was weighed into a 30 mL Teflon
container, and 2 mL of concentrated HNO3 was added. The
container was then covered with Teflon and heated at 50 °C
for 2 h. After it was cooled to room temperature, 1 mL of
HClO4 was added, and the container was placed in a stainless
steel bomb which was then sealed tightly with a screw closure
to avoid any leakage and placed in an oven. The oven
temperature was raised to 170 °C and kept for 7 h. After
cooling, the Teflon container was taken out of the stainless
steel bomb, and the Teflon cover was removed. The container
was heated on a hot plate, and the solution was evaporated
until fumes of HClO4 nearly disappeared. The residue was
transferred into a volumetric flask and diluted to 10 mL with
0.01 M HNO3. The solution was then ready for ICP-MS
analysis.
3. Results and Discussion
3.1. Sample Pretreatment. Organotins or Sn(IV) present in
biological samples were detected quantitatively by an
analytical procedure consisting of the basic steps of preparation. Treatment with sulfuric acid was to digest the organic
samples so that the inorganic particles (carbonates, sulfides)
could be dissolved to release eventual inclusions of organotin
compounds (16). Because the flame photometric detector
was also sensitive to sulfide, it was important to add CuSO4
solution to form CuS deposit. Thus the disturbance of S2- in
the sample matrix could be effectively eradicated. The
addition of KBr was used to increase the ion strength of the
aqueous phase, which helped to better the extraction of the
tin-tropolone complexes by the organic solvent cyclohexane
used in this experiment. The pH range, which allowed
quantitative extraction of all species, was strictly limited.
Me3Sn+, Me2Sn2+, and MeSn3+ could be completely extracted
(more than 90%) only at pH 5 (17). We used citric acidphosphate buffer solution (pH ) 5.0), which ensured the
complete extraction of all compounds interested. As mentioned previously (18), the use of tropolone was one of the
important factors affecting recovery efficiency. It could greatly
improve the recoveries of organotins and Sn(IV) (19, 20).
However, it was noted that poor extraction efficiencies could
result if the tropolone solution was prepared 18 h earlier
(21); therefore, the tropolone-cyclohexane solution should
be prepared immediately before extraction of the aqueous
phase (R. J. Maguire et al. recommended less than 5 min
(21)). In our study, the extraction solutions used were all
freshly made.
3.2. The Selection of the Alkylation Group. The most
frequently used methods for the conversion of ionic alkyltins
into gas chromatographiable species were (1) in stiu hydridization using NaBH4 or ethylation with NaBEt4 and (2)
derivatization by the Grignard reaction. The corresponding
hydrides and ethylated products were usually more volatile
and easily escaped during the sample pretreatment, especially
for the organotins with small organic groups such as methyltin
compounds, while the Grignard alkylation reaction could
proceed quantitatively, leading to stable derivatives when it
was carried out in a suitable solvent. So it is more feasible
to analyze methyltin compounds here. The Grignard propylation and pentylation were the usual choice as they have
not been introduced into the environment yet and also
allowed a simultaneous speciation analysis of methyl-, butyl-,
phenyl-, and cyclohexyltin species (22). As discussed earlier
(23-25), the use of n-pentyl derivatives for the determination
FIGURE 1. Chromatogram of pentylated standards and internal
standard. Peaks are identified as 1. solvent (1 µL of cyclohexane,
tR: 0.53 min); 2. TMT (0.10 ng as Sn, tR: 1.90 min); 3. internal standard
(0.2 ng as Sn, tR: 4.41 min); 4. DMT (0.15 ng as Sn, tR: 6.98 min); 5.
MMT (0.20 ng as Sn, tR: 10.91 min); and 6. inorganic Sn(IV) (0.5 ng
as Sn, tR: 14.01 min).
FIGURE 3. Chromatogram of the blank heart sample. Peaks are
identified as 1. solvent (2 µL of cyclohexane, tR: 0.53 min), no
methyltins were detected; 2. internal standard (tR: 4.41 min); and
3. Sn(IV) (0.22 µg/g as Sn, tR: 13.93 min).
TABLE 2. Organotin Concentrations Determined in Organ
Samples (µg/g as Sn)a,b
sample
DMTc
TMT
Sn(IV)
total
tind
heart
liver
stomach
kidney
blank heart
blank liver
blank stomach
blank kidney
0.100 ( 0.00e
1.93 ( 0.04
0.104 ( 0.003
1.05 ( 0.02
ND f
ND f
ND f
ND f
1.48 ( 0.03
1.42 ( 0.07
0.304 ( 0.007
0.47 ( 0.01
ND f
ND f
ND f
ND f
0.22 ( 0.01
0.24 ( 0.01
0.290 ( 0.010
0.173 ( 0.005
0.224 ( 0.001
0.594 ( 0.001
0.347 ( 0.001
0.184 ( 0.000
1.82
5.02
0.84
3.45
0.05
0.03
0.19
0.10
a Five times replicated measurements. b The formula, the calculation
was based on, was the following: Cx/CI ) fx*hx/hI (Cx was the
concentration of the compound to be detected; CI was that of the internal
standard; fx was the corresponding calibrate coefficient; hx was the
peak height of the compound to be detected; and hI was that of the
internal standard). c The concentration of the compound (as Sn).
d Measured by ICP-MS, others measured by GC-FPD. e The wet weight
of organs. f Not detected, ND.
FIGURE 2. Chromatogram of the kidney sample. Peaks are identified
as 1. solvent (2 µL of cyclohexane, tR: 0.45 min); 2. TMT (0.47 µg/g
as Sn, tR: 1.98 min); 3. internal standard (tR: 4.44 min); 4. DMT (1.05
µg/g as Sn, tR: 7.00 min); and 5. Sn(IV) (0.17 µg/g as Sn, tR: 13.96
min).
of ionic alkyltin compounds by the hyphenated techniques
has several advantages. It led to less volatile analytes than
ethylation, which facilitated further preconcentration and
cleanup steps, and the n-pentyl derivatives studied here were
also volatile enough to avoid the condensation problems in
the interface during GC-FPD analysis.
3.3. Analysis of Tin Compounds in Organ Samples. 3.3.1.
Identification of Organotins in the Samples. The existence of
methyltin compounds in the lard sample was identified by
GC-MS, which was in good accordance with the chromatogram obtained by standard pentylated methyltin compounds.
Therefore, according to the retention time of standards, each
compound of interest in the organ samples can be easily
identified. Figure 1 showed the GC-FPD chromatogram of
pentylated standard organic and inorganic tin compound.
Figures 2 and 3 showed the chromatograms obtained from
the victim’s kidney and the blank heart as examples. It was
obvious that tri-, dimethyltin, and inorganic tin were found
in all four organs, while in the blank organ samples, inorganic
tin was the only tin compound found.
3.3.2. Measurements of Each Tin Species and Total Tin in
the Samples. The introduction of an internal standard allowed
for the correction of dilution errors and generally confirmed
the whole proper operation and gave much greater reliability
than the other methods (17). The calibration coefficients fi
of the target standard compounds relative to the internal
standard were obtained by this method. Its precision,
estimated to be five times the repetitive determination of
the standard sample, averaged at 4.2%, while the relative
standard deviation ranged from 3.0% to 5.0%. The concentrations of all tin compounds in victim’s organs and blank
organs were then measured by the basic formula of the
internal standard method. The results were depicted in Table
2, which showed that the concentrations of all object
compounds in each sample ranged between 0.10 and 1.93
VOL. 34, NO. 13, 2000 / ENVIRONMENTAL SCIENCE & TECHNOLOGY
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FIGURE 4. The distribution of tin compounds in organ samples.
FIGURE 5. The distribution of main trace metal elements in organ samples.
µg/g (wet weight). The amount of total tin was quantified by
ICP-MS using In as the internal standard. The concentrations
ranged between 0.03 and 5.02 µg/g (wet weight) which were
also listed in Table 2. The distribution of tin compounds and
total tin in each organ sample were shown in Figure 4. It was
obvious that the concentrations of inorganic tin in the
poisoned organs were equivalent to those in the blank ones,
and the amounts of methyltins were rather high in the victim’s
key organs while in the blank organs they were not detected.
As tin’s inorganic salts had low toxicity, we could easily
conclude that the victim’s death was a result of poisoning
due to the high concentrations of methyltins which greatly
exceeded the amounts that a normal human body could bear.
3.3.3. The Action Mechanism of Organotin Compounds.
The availability of pollutants to organisms is a key determinant for the interaction of toxicants with biota, and thus
for uptake, accumulation, and toxicity. Organotin bioavailability depends on ambient media, such as solvent, temperature, pH, and ionic composition. Organotins are hy2700
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ENVIRONMENTAL SCIENCE & TECHNOLOGY / VOL. 34, NO. 13, 2000
drophobic compounds, and oily edible lard is a good solvent
for them. When the containers used for containing lard were
contaminated with organotins, mainly DMT, just as the
accident occurred in several districts in eastern China’s Jiangxi
province, the lipophilic contaminants dissolved in lard
completely and were ingested and absorbed by the local
people who ate the lard. As shown in Table 2, the amounts
of methyltins focused in organs were rather high.
The pH in ambient media is known to alter the bioavailability of organometallic compounds. When the surrounding
pH is lower than the pKa of organotins, the compounds are
dissociated and the dominant species are the cations, whereas
at the pH higher than pKa, neutral compounds are dominant.
Neutral species are stable and facilitate to be sorbed by
organisms and can penetrate biomembranes much more
easily than the charged, hydrophilic cations, which then
results in higher bioaccumulation and toxicity. Higher H+
concentration at pH lower than pKa can induce physiological
effects on epithelial surfaces due to modification in the
TABLE 3. Total Amounts of 11 Trace Metal Elements in Organ Samples (µg/g)
poisoned body
unpoisoned body
element
heart
liver
stomach
kidney
heart
liver
Cr52
1.013
0.028
0.487
NDa
3.251
0.008
0.041
0.532
0.508
1.818
1.852
0.058
0.057
0.936
0.123
0.212
10.155
14.743
0.007
0.520
16.559
16.748
5.015
4.970
0.052
0.389
0.552
0.009
0.156
1.380
1.709
0.003
0.051
0.767
0.823
0.840
0.837
0.018
0.139
0.680
0.020
0.202
2.799
15.883
0.008
0.438
61.723
66.304
3.448
3.503
0.055
0.210
0.121
0.004
0.009
0.433
1.839
NDa
0.030
0.088
0.091
0.048
0.041
0.005
0.054
0.484
0.039
0.214
1.122
14.992
0.005
0.165
4.738
4.889
0.096
0.100
0.034
0.515
Co59
Ni60
Cu65
Zn66
Ge74
Se82
Cd112
Cd114
Sn118
Sn120
Hg202
Pb208
a
stomach
kidney
0.169
0.007
0.053
NDa
1.523
0.001
0.023
0.649
0.708
0.031
0.029
0.288
0.080
0.249
0.009
0.086
0.206
6.192
0.003
0.225
24.790
26.448
0.194
0.187
0.009
0.183
Not detected, ND.
structure, fluidity, or permeability of the cell membranes.
Experiments with Daphnia showed that the neutral lipophilic
tributyltin (TBT) has higher fluidity and penetrated the cell
membranes more efficiently than the less lipophilic cation,
and the presence of humic acids and dioctyltin (DOC) led
to a reduction in TBT bioaccumulation due to their interaction with TBT. A low pH of stomach juice changed neutral
DMT and TMT to charged cation and organic acid reacted
with DMT and TMT cations to form large complexes,
therefore reduced the permeability, which may explain the
lower concentration of DMT and TMT in the victim’s
stomach. Lack of organic moiety prevented inorganic tin
from penetrating the cell membranes easily which resulted
in relatively lower Sn(IV) concentration in four organs.
Compared to the liver, the relative lower concentration of
DMT, TMT, and Sn(IV) in the kidney may result in metabolism
with urine which bring lots of wastes and toxicants out of the
body. The neutral DMT and TMT penetrated through the
biomembrane and circulated with body fluid, eventually
being concentrated in the liver to be dissociated by bile. The
higher concentration of DMT and TMT in the liver may result
in its antitoxic action.
Besides TBT, probably triphenyltin (TPT) as well was
demonstrated to degrade in water and sediments under biotic
and abiotic processes (26-29). Biogenic productions are
suspected for methyltins as the result of the trans-methylation
of inorganic tin. The possible formation of TMT under
oxygenous conditions by algea and stannane under anoxic
medium was also described (30, 31). The biotransformation
of methyltins in humans is not clear yet. Both contradiction
processes of degradation and methylation seem to be
coexistent, since TMT and Sn(IV) were also detected in the
four organ samples although no contaminants other than
DMT were identified in the poisoning lard. Higher concentration of TMT and lower concentration of Sn(IV) may induce
that biomethylation of DMT and Sn(IV) to TMT probably
dominated degradation of DMT and TMT to Sn(IV). Degradation of one DMT can provide two methyl groups for
methylation of two DMTs.
3.4. Analysis of Major Trace Metal Elements in Organ
Samples. The total amounts of major trace metal elements
such as Sn, Cd, Zn, Cu, etc. were detected by ICP-MS using
In as the internal standard. The results were shown in Table
3, and the distribution of main metal elements in organ
samples was shown in Figure 5. It was clear that in all of the
victim’s organs, total tin content was rather high, and it was
the dominant factor that led to death. Because the detailed
forms of other elements except Sn existing in the human
body are unclear, their toxicity to the human body could not
be accurately estimated. Perhaps they are also a factor in the
death. But if we considered tin compounds in the organs
only, it would be enough for the toxic trimethyltin to poison
the victim resulting in the victim’s death. In addition, since
the lard that the poisoned victims ate was contaminated
with the tin species, mainly dimethyltin, it is believed that
the tin element should be held more responsible for the
deaths rather than the other trace metals.
Acknowledgments
This work was jointly supported by National Natural Science
Foundation of China under contract No. 29825114 and
Chinese Academy of Sciences under contract Nos. KZ951B1-209 and RCEES9902.
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Received for review January 7, 2000. Revised manuscript
received March 30, 2000. Accepted April 5, 2000.
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