Journal of Chromatography A, 1127 (2006) 154160

Determination of sulfonamides in selected Malaysian swine

wastewater by high-performance liquid chromatography
Nancy T. Malintan , Mustafa Ali Mohd 1
Department of Pharmacology, Faculty of Medicine, University of Malaya, 50603 Kuala Lumpur, Malaysia
Received 28 February 2006; received in revised form 22 May 2006; accepted 1 June 2006
Available online 27 June 2006

Abstract
An analytical HPLC method for the simultaneous determination of eight sulfonamides in swine wastewater was developed. The samples were
collected from three states in Malaysia. Sample clean up was carried out by employing solid-phase extraction using a 60 mg Oasis HLB (Waters)
cartridge with 3 ml reservoir. The HPLC column used was Supelcosil C18 (250 mm 4.6 mm I.D.) and elution was carried out using gradient
mode. The mobile phases used were acetonitrile and 0.5% acetic acid in purified water. Antibiotics were detected using UV absorbance at
272 nm. Recoveries obtained for sulphanilamide ranged from 31.9 5.1% to 36.2 1.0%, while recoveries for other sulfa drugs studied were
from 91.9 5.0% to 106.0 1.1%. The limit of quantitation (LOQ) for sulfamerazine, sulfamethazine and sulfamethoxypyridazine was 7.5 ng/L,
while the LOQ for the other studied antibiotics was 5.0 ng/L. The method was used to analyse sulfonamides in wastewater collected from selected
Malaysian swine facilities.
2006 Elsevier B.V. All rights reserved.
Keywords: Antibiotic; Sulfonamide; HPLC; Waste water; Aquatic environment; Pharmaceutical contaminant

1. Introduction
Antibiotics are used in human and veterinary medicines to
treat diseases and as prophylaxis [14]. There is a significant
increase in the frequencies of detecting antibiotic residues in
the aquatic environment either in the natural water system or in
the water treatment facilities, thus posing a potential of indirect
human exposure to the residues through contaminated drinking water supplies [5]. There is also a global concern over the
veterinary application of antibiotics particularly due to the escalating spread of resistance in pathogens. The risk of developing
bacterial resistance had been intimately linked with the use of
antibiotics in animal husbandries [4,6,7].
Antibiotics from veterinary application could be transported
into the aquatic environment. Depending on the nature of the
drugs themselves, there are variations in the behaviour of these
antibiotics in the environment. It has been reported that sulfon

Corresponding author. Tel.: +60 37967 6619/4709;

fax: +60 37967 6620/4791.
E-mail addresses: ntmalintan@gmail.com (N.T. Malintan),
mustafa@ummc.edu.my, medicine7@hotmail.com (M.A. Mohd).
1 Tel.: +60 12377 7757/37967 4709; fax: +60 37967 4091/2055.
0021-9673/$ see front matter 2006 Elsevier B.V. All rights reserved.
doi:10.1016/j.chroma.2006.06.005

amides have high potential to resist degradation [1,6,8]. This was

attributed to their hydrophilic entity, enabling them to be transferred into the aquatic environment. A study conducted by Alder
et al. [9] at a lake surrounded with intensive farming indicated
higher concentration of sulfamethazine, a sulfonamide derivative, in the lake compared to the wastewater treatment plant of the
same area. Another study carried out by Campagnolo et al. [10]
detected multiple classes of antibiotics in the wastewater and
water resources near to the swine and poultry farms. Groundwater analysis by Batt et al. [11] resulted in the detections of
two sulfonamides; sulfamethazine and sulfadimethoxine, both
of which are to be used in veterinary application. The groundwater source was closed to the confined animal feeding operation
(CAFO) area. This suggested that the source of antibiotics contamination in the environment could be from animal origin
besides human medicine.
Sulfonamides are still widely used in livestock productions
for their therapeutic and prophylactic properties [1214]. The
widespread use of sulfonamides in farming and failing to observe
the withdrawal period resulted in the presence of sulfonamides
traces in the meat products. Because of concerns they posed on
human health and for regulatory purposes, the European Union
(EU) had drawn a maximum residual level (MRL) of 100 g/kg

N.T. Malintan, M.A. Mohd / J. Chromatogr. A 1127 (2006) 154160

of sulpha drugs in animal products. Several methods have been

developed to determine sulfonamides in animal tissues [1315].
A very sensitive method is required for the study of antibiotic residues in environmental samples, particularly wastewater.
Several chromatographic methods have been developed for the
analysis of sulfonamides in environmental samples [4,6,14,16].
Our method in particular, was developed for the analysis of
sulfonamides in wastewater collected from the swine facilities.
Following this, proper strategies could be developed to monitor
the use of sulfonamides in swine farming. Analytical instruments
coupled with mass spectrometric detection such as GCMS and
LCMS were favoured by many analysts due to their higher
sensitivity and their ability to provide compound confirmation.
GCMS, however, is not suitable for sulfonamides due to the
low volatility of sulfonamides. Derivatisation could overcome
the problem but the process would increase the preparation
time, especially with a large batch of samples. LCMS may
be another option but this technique is more expensive and not
available in many routine laboratories in Malaysia. HPLC methods were successfully applied in determining sulfonamides in
animal products and feeds [13,15]. Limited methods were available to determine sulfonamides in wastewater using HPLC as
most of the published methods for water analysis utilised chromatographic separation coupled with mass detectors [4,1721].
Hilton and Thomas [19] were able to determine pharmaceutical
products and metabolites in sewage effluent using a more sophisticated technique: LCelectrospray ionization (ESI)MS/MS.
Lindberg et al. [20] were able to determine six antibiotic groups
in hospital sewage also by using LCMS. The method by Yang
et al. [21] was designed to simultaneously analyse two classes of
antibiotics: tetracyclines and sulfonamides in domestic wastewater, also by using LCMS. In the present study, we developed an analytical method using HPLC, as HPLC remained the
main tool of analysis in most service, commercial and research
laboratories.
In this article, we discussed the HPLC method developed to
simultaneously determine eight sulfa derivatives in the waste
water collected from swine facilities in Malaysia. The eight
sulfa drugs included in this study were recommended by the
Malaysian Veterinary Department as these drugs have the potential of being used in animal husbandry in Malaysia. The chemical
properties of the sulfonamides studied were given in Table 1
(Fig. 1).

155

2. Experimental
2.1. Chemicals and materials
The sulfonamide standards were from SigmaAldrich with
99.8% purity. The sulfonamides used were sulfanilamide (SAD),
sulfadiazine (SDZ), sulfathiazole (STZ), sulfamerazine (SMR),
sulfamethazine (SMZ), sulfamethoxypyridazine (SMPD), sulfadimethoxine (SDM) and sulfaquinoxaline (SQX). All chemicals used were of analytical and HPLC grades while ultra-pure
water was used in the analysis. The water was purified using a
Milli-Q system (Milli-Q BioCel) at 18.2 M
cm with a 0.22 m
filter. All solvents for HPLC application were filtered before
use with the 0.45 m membrane filter paper (Millipore) and
degassed by ultrasonication for 30 min before use.
Oasis (Waters, Milford, MA, USA) cartridges with 60 mg
packing material and 3 ml reservoir of the hydrophilic-lipophilic
balance (HLB) type were used in sample preparation.
2.2. Calibration curve
Sulfonamide stock solutions were prepared by dissolving
10.0 0.1 mg of each standard in 10 ml methanol resulting in
1 mg/ml stock solutions and kept in 80 C. A working standard of sulfonamides mixture was prepared at the concentration
of 100 g/ml in MeOH. This working standard was used to prepare the calibration curve. The standards were evenly distributed
into eight concentrations between 5.0 and 100.0 ng/L. Sample
volumes of 50 l were analysed in six replicates for the determination of the calibration curve. Calibration curve was based
on an external standards mixture.
2.3. Sample preparation
Sulfonamides were extracted from 150 ml waste water samples. The solid-phase extraction (SPE) (Oasis HLB) cartridges
were conditioned with 3 ml methanol followed by 3 ml of 0.5 M
HCl, followed by equilibration with 3 ml deionised water. Immediately after sample loading, 1 ml of deionised water was introduced to the cartridges. Sulfonamides was eluted using 5 ml
of ammoniated methanol (ammonia:methanol, 1:19, v/v) and
allowed to dry under nitrogen stream in a 35 C water bath.
The dried extract was reconstituted in 500 l mobile phase. The

Table 1
Chemical properties of the sufonamides [2224]
No.

Compound

CAS No

pKa value (MW)

Usage

1
2
3
4
5
6
7
8

Sulfanilamide
Sulfadiazine
Sulfathiazole
Sulfamerazine
Sulfamethazine
Sulfamethoxypyridazine
Sulfadimethoxine
Sulfaquinoxaline

63-74-1
68-35-9
72-14-0
127-79-7
57-68-1
80-35-3
122-11-2
59-40-5

10.43 (172.21)
6.4 (250.28)
7.2 (255.32)
7.0 (322.43)
7.4 (278.33)
6.7 (280.31)
6.2 (310.33)
5.5 (300.34)

Bacteriostatic
Bacteriostatic. Usually co-administered with trimethophrim.
Bacteriostatic
Bacteriostatic
Bacteriostatic
Bacteriostatic
Bacteriostatic. Usually co-administered with trimethophrim.
Bacteriostatic

156

N.T. Malintan, M.A. Mohd / J. Chromatogr. A 1127 (2006) 154160

Fig. 1. Molecular structures of the studied compounds.

efficiency of sulfonamides extraction was judged by comparing the concentrations of fortified samples to the corresponding
standards.

3. Results and discussion

2.4. HPLC parameters

The method developed is used to separate the eight sulfonamides using water and acetonitrile as mobile phases. The
method developed in this study does not involve the use of buffer
as mobile phase, which is not desirable in most HPLC analysis. Most of the published methods used buffer as mobile phase
[4,6,12] for the analysis of sulfonamides, and the matrix used
are either tissue samples or other environmental samples such
as manure and feed besides wastewater. The amphotheric nature
of sulfonamides makes their separation difficult. However, our
experiment revealed that water and acetonitrile worked as effective as the buffer and other solvents combination. Furthermore,
avoiding the use of buffer may prolong the lifetime of the HPLC
column. Salt traces from the buffer tend to crystallise in the
column and reduced its separation capacity.
Acetic acid (0.5%) was added into the mobile phase to
enhance the peak resolution and sensitivity. In the absence of
acid, co-elution of STZ/SMR, SMZ/SMPD and SDM/SQX were
observed. This observation was also made in the study by Fuh
and Chan [14].
The limit of quantitation (LOQ) was determined experimentally where sulfonamides standard mixture was spiked into the

The analyses were carried out on a Shimadzu LC10 AT Class

VP HPLC system (Shimadzu, Japan) equipped with UV detector and column oven. The detection wavelength was 272 nm
and the oven temperature was set at 35 C. A Supelcosil C18
HPLC column (250 mm 4.6 mm I.D., 5 m) was used for separation. The mobile phases used were (A) 0.5% acetic acid
in ultra-pure water and (B) acetonitrile. A gradient chromatographic elution was obtained by initially running 90% A, held
for 15 min, descended to 78% in 2 min and held for 8 min followed by increment of A phase to 80% in 3 min. The run was
completed in 35 min. The flow was set at 1 ml/min. 10 min were
allowed in-between runs for re-equilibration of the column by
reverse gradient.
2.5. Validation
This method was validated for the water sample analysis.
Parameters included in the validation were linearity, precision,
accuracy, selectivity and stability.

3.1. HPLC method development

N.T. Malintan, M.A. Mohd / J. Chromatogr. A 1127 (2006) 154160

157

Table 2
Summary of the calibration curve equations obtained from six replicates
No.

Studied compound

Mean SD (n = 6)
Slope of calibration curve (m)

1
2
3
4
5
6
7
8

Sulfanilamide
Sulfadiazine
Sulfathiazole
Sulfamerazine
Sulfamethazine
Sulfamethoxypyridazine
Sulfadimethoxine
Sulfaquinoxaline

23.6
14.5
63.9
27.9
54.6
71.3
79.2
57.8

0.1
0.1
0.0
0.1
0.1
0.1
0.1
0.0

deionised water samples, extracted and analysed until the lowest concentration with acceptable precision and accuracy was
reached. The LOQ established were 5.0 ng/L for SAD, SDZ,
STZ, SDM and SQX, whereas SMR, SMZ and SMPD had the
LOQ of 7.5 ng/L.
3.2. Calibration curve
Linear calibration curve was developed for all compounds
by spiking the standards into deionised water. The calibration
curves were within the range of 5.0 ng/L to 100.0 ng/L. Linear curves were obtained with coefficient of determination (R2 )
of 0.99. The reproducibility was also tested with six replicates
and the relative standard deviations (RSDs) were all less than
5.5%. The acceptance criterion was not more than 15.0%. The
calibration curve equations are summarised in Table 2.
3.3. Sample preparation
The differences in the pKa of the sulfonamides in this study
made sample extraction difficult. The extraction method was
modified from Lindsey et al. [17]. The published methods
indicated sulfonamides were best extracted in acidic condition
[13,16,17], but when the samples were acidified, the recoveries for the compound SAD were markedly reduced. This could
be due to the fact that SAD had a pKa value of 10.43 which
is favoured in alkaline condition. However, if the extraction
were carried out in an alkaline condition, the recoveries for the
rest of the compounds will be reduced. Therefore, we decided

Coefficient correlation (R2 )

Y-axis intercept (c)

33.5
76.8
28.0
43.3
160.7
365.9
227.1
222.4

5.3
1.7
2.4
1.8
2.3
2.7
3.8
2.5

0.9989
0.9901
0.9922
0.9908
0.9959
0.9911
0.9909
0.9998

0.0001
0.0060
0.0001
0.0006
0.0001
0.002
0.0003
0.0001

not to adjust the sample pH to accommodate all the antibiotics

analysed. The recoveries were found to be very good. Attempt
was also made to reproduce a method that used stacked SPE
cartridges but the recoveries obtained were not satisfactory. Furthermore, the use of double cartridges would only increase the
analysis cost. The recoveries were much improved with Oasis
HLB cartridges. The recoveries of sulfonamides were then evaluated at three concentration levels; 10.0 ng/L, 25.0 ng/L and
100.0 ng/L being the low, median and high QC concentrations.
The recoveries were within the range of 30.8% to 105.1% fortified at the low concentration, 33.8% to 106.8% at median
concentration and within 35.9% to 108.3% when fortified at the
high concentration. The recoveries of all compounds were summarised in Table 3. Recovery study was done by extracting the
analytes at the QC concentrations from deionised water. For the
quality assurance test on the method, bracketing was done every
tenth analysis by running the QC concentrations. This was to
check the performance of the method. The analysis was continued if the values from the check-run were within the acceptable
precision and accuracy.
3.4. Validation procedures
Comparison of the chromatograms of the spiked deionised
water samples against the blank water samples showed the selectivity of the method (Fig. 2). Blank samples used were the
unspiked deionised water (Fig. 3). HPLC, unlike GCMS and
LCMS lacks the ability to provide compound confirmation.
Therefore selectivity of the method was evaluated by comparison

Table 3
Recoveries and LOQ of sulfonamides spiked at three concentration levels; low (10.0 ng/L), median (25.0 ng/L) and high (100.0 ng/L) obtained from six replicates
No.

Studied compound

LOQ (ng/L)

Mean recovery RSD (%)

10.0 ng/L

1
2
3
4
5
6
7
8

Sulfanilamidie
Sulfadiazine
Sulfathiazole
Sulfamerazine
Sulfamethazine
Sulfamethoxypyridazine
Sulfadimethoxine
Sulfaquinoxaline

5.0
5.0
5.0
7.5
7.5
7.5
5.0
5.0

31.9
92.9
101.1
97.7
100.0
98.8
98.0
99.0

5.1
3.8
2.1
3.1
0.8
1.7
1.3
2.4

25.0 ng/L
34.6
91.9
99.4
99.2
99.4
96.1
101.4
95.0

4.8
5.0
0.4
0.3
1.6
1.0
1.9
0.9

100.0 ng/L
36.2
92.6
106.0
98.5
98.4
99.2
99.5
97.9

1.0
5.4
1.1
2.4
2.4
0.8
2.3
1.6

158

N.T. Malintan, M.A. Mohd / J. Chromatogr. A 1127 (2006) 154160

Fig. 2. Chromatogram of extracted deionised water samples fortified with mixture of pure sulphonamide standards at the concentration of 10.00 ng/L. Retention
times (min) for each compound were: SAD 4.55 0.01, SDZ 8.30 0.01, STZ 10.62 0.02, SMR 12.60 0.03, SMZ 19.03 0.08, SMPD 20.92 0.04, SDM
33.04 0.13, SQX 34.81 0.16.

of the compound retention time obtained from the chromatogram

of fortified deionised water to the chromatogram of unfortified
deionised water.
Precision and accuracy of the method were evaluated at
three concentration levels (QC levels) being the low (10.0 ng/L),
median (25.0 ng/L) and high (100.0 ng/L) at six replicates per
concentration. The within-day precision and accuracy ranged
from 3.5 0.1 ng/L to 107.0 1.4 ng/L for the low, median
and high QC levels. Meanwhile, the between-day precision
and accuracy yielded concentrations between 3.2 0.2 ng/L
and 106.0 1.2 ng/L for the low, median and high QC

levels. The results of precision and accuracy were summarised

in Table 4.
The long-term stability study indicated that the compounds
in the processed samples were stable for the period of sixteen
weeks when stored in 80 C. The relative standard deviations obtained were less than 15.0%. Stability was evaluated
at the high (100.0 ng/L) and low (10.0 ng/L) concentrations.
When fortified at high level, the measured concentrations were
from 35.9 1.4 ng/L to 99.1 4.4 ng/L and at the low level,
the measured concentrations were between 3.6 0.2 ng/L and
9.7 0.4 ng/L. The results were summarised in Table 5.

Fig. 3. Chromatogram of extracted unfortified deionised water sample in the simultaneous analysis of SAs +CAP.

N.T. Malintan, M.A. Mohd / J. Chromatogr. A 1127 (2006) 154160

159

Table 4
Summary of precision and accuracy for the analysis of sulfonamides spiked at low (10.0 ng/L), median (25.0 ng/L) and high (100.0 ng/L) concentrations obtained
from six replicates
No. Studied compound
Spiked

Within-day
Mean concentration RSD (bias %)
10.0 (ng/L)

1
2
3
4
5
6
7
8

Sulfanilamide
3.5 3.6 (65.0)
Sulfadiazine
9.9 0.8 (1.3)
Sulfathiazole
9.8 1.4 (1.6)
Sulfamerazine
10.2 1.9 (1.8)
Sulfamethazine
9.9 1.6 (1.18)
Sulfamethoxypyridazine 9.9 3.9 (0.6)
Sulfadimethoxine
10.0 1.3 (0.5)
Sulfaquinoxaline
10.2 3.6 (1.9)

Between-day
Mean concentration RSD (bias %)

25.0 (ng/L)
9.3
25.1
25.2
24.9
25.0
25.5
24.4
24.7

100.0 (ng/L)

2.2 (62.7)
1.1 (0.4)
1.4 (1.0)
0.8 (0.3)
1.8 (0.1)
2.5 (5.9)
1.4 (2.3)
2.7 (1.0)

36.7
101.7
107.0
97.8
103.5
100.3
104.4
105.6

10.0 (ng/L)

1.0 (63.3) 3.2 5.1 (68.1)

0.4 (1.7)
9.3 3.8 (7.1)
1.3 (7.0)
10.1 2.1 (1.1)
2.2 (2.2)
9.8 3.1 (2.3)
5.0 (3.5)
10.0 0.8 (0.0)
1.5 (0.3)
9.9 1.7 (1.2)
0.8 (4.4)
9.8 1.3 (2.1)
3.3 (5.6)
9.9 2.4 (1.0)

25.0 (ng/L)
8.6
23.0
24.9
24.8
4.9
24.2
25.3
23.8

100.0 (ng/L)

4.8 (65.4) 36.2 1.0 (63.8)

5.0 (8.1)
92.6 5.4 (7.4)
0.4 (0.6) 106.0 1.1 (6.0)
0.3 (0.6)
98.5 2.4 (1.5)
1.6 (3.1)
98.4 2.4 (1.6)
1.0 (3.1)
99.2 0.8 (0.8)
1.8 (1.2)
99.5 2.3 (0.5)
0.9 (5.0)
97.9 1.7 (2.1)

Table 5
Long-term stability of extracted sulfonamides for sixteen weeks spiked at low (10.0 ng/L) and high (100.0 ng/L) concentrations obtained from two replicates
No.

Studied compound
Spiked concentration

Mean concentration RSD (bias %)

10.0 (ng/L)

1
2
3
4
5
6
7
8

Sulfanilamide
Sulfadiazine
Sulfathiazole
Sulfamerazine
Sulfamethazine
Sulfamethoxypyridazine
Sulfadimethoxine
Sulfaquinoxaline

3.7
9.3
9.3
9.3
9.5
9.2
9.3
9.8

6.9 (65.3 2.5)

5.8 (7.9 5.4)
6.2 (8.3 3.9)
4.9 (6.9 4.5)
3.6 (4.9 3.5)
3.4 (8.0 3.2)
4.8 (6.9 4.5)
4.3 (0.4 0.2)

Mean concentration RSD (bias %)

100.0 (ng/L)
35.9
92.1
98.9
94.7
97.1
96.9
97.7
99.1

4.0 (64.1 1.4)

4.0 (7.9 3.7)
3.8 (2.9 2.4)
1.7 (5.3 1.6)
1.5 (3.0 1.5)
5.4 (3.1 5.2)
2.7 (3.1 1.5)
4.5 (3.7 2.4)

Fig. 4. Chromatogram of wastewater sample found to contain antibiotic. The sample was positive for SAD.
Table 6
Wastewater analysis in the samples collected from Perak, Malacca and Selangor
Location (n = 100)

Number of positive sample

Sulfa detected

Detection range (ng/L)

Perak
Malacca
Selangor

31
41
31

SAD, SDZ, SMR, SMZ, SMPD

SAD, SDZ, STZ, SMR, SMPD, SDM
SAD, SDZ, STZ, SMR, SMPD, SDM, SQX

5.1593.75
5.0394.15
5.1294.95

160

N.T. Malintan, M.A. Mohd / J. Chromatogr. A 1127 (2006) 154160

ment, Selangor. The study was supported by Shimadzu-UMMC

Centre for Xenobiotic Studies (SUCXeS), University Malaya
and Vote F (F0160/2005A) from the University of Malaya.
References

Fig. 5. Total concentrations of sulfonamides detected in the wastewater samples

collected from Perak, Malacca and Selangor.

3.5. Analysis of sulfonamides in wastewater

This method was applied in the analysis of 300 waste water
samples collected from the swine facilities. The samples were
collected in two sampling cycles from three states in Malaysia:
Perak, Malacca and Selangor. A total of 103 samples were found
positive for sulfonamides (Fig. 4). The results were tabulated in
Table 6 and the sulfonamides detected were shown in Fig. 5.
4. Conclusion
This study demonstrated the reliability of HPLC method
in the simultaneous determination of eight sulfa derivatives in
wastewater. The method has the quantification limit of 5.0 ng/L.
In conclusion, the method developed in this study was simple and
efficient with adequate sensitivity and reliability for its application in routine analysis. The study on selected swine wastewater
showed that traces of sulfonamides are present in water from
animal husbandries activities.
Acknowledgements
The authors would like to thank Dr. K. Loganathan, Ms.
Marni Sapar and the staff of Petaling Jaya Veterinary Depart-

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