Soil & Sediment Contamination, 17:111, 2008

Copyright Taylor & Francis Group, LLC

ISSN: 1532-0383 print / 1549-7887 online
DOI: 10.1080/15320380701741263

Determination of Organochlorine Pesticides

from Agricultural Soils Using Pressurized
Liquid Extraction
D. VEGA MORENO,1 Z. SOSA FERRERA,1
` 2
J.J. SANTANA RODRIGUEZ1 , E. POCURULL AIXALA,
2
AND F. BORRULL BALLARIN
1
2

University Las Palmas de Gran Canaria, Las Palmas de Gran Canaria, Spain
University Rovira i Virgili, Tarragona, Spain
A method to determine thirteen organochlorine pesticides from soils samples has been
developed using pressurized liquid extraction (PLE) and gas chromatography electroncapture detection. The variables optimized have been: type of solvent, number of cycles,
temperature, time, flush volume and pressure. The optimal conditions have been hexaneacetone (1:1), 1 cycle, 50 C, 60% of flush volume and 1500 psi.
The results obtained indicate that most of these compounds can be recovered quantitatively with RSDs lower than 10% and detection limits ranged between 0.3200 ngkg 1
for the pesticides studied. Under the optimized conditions, the proposed method has been
applied to the analysis of agricultural soils. Aldrin and p,p -DDT have been found in
most of these samples at low gkg 1 levels.
Keywords Organochlorine pesticides, soils, pressurized liquid extraction, gas
chromatography-electron capture detection

Introduction
During more than half a century organochlorine pesticides have been used as insecticides
in agriculture and for the control of vector-borne diseases. Developed countries banned
these compounds in 1970s, but some countries have continued to use DDT, especially for
public health applications such as malaria control (Kusvuran and Erbatur, 2004; Stockholm
Convention, 2001). Organochlorine pesticides can be found in the environment, in spite
of their prohibition, due to the long-term persistence of them in soil (Shivaramaiah et al.,
2002; Chen et al., 2002; Nawab et al., 2003; Megharaj et al., 2000).
Their lipophilic nature, hydrophobicity and low chemical and biological degradation
rates have led to their accumulation in biological tissues and subsequent magnification of
concentrations in organisms progressing up the food chain with consequences for humans
(Mwevura et al., 2002; Maroni et al., 2000). For these reasons they are listed as US Environmental Protection Agency (EPA) priority pollutants (US EPA, 1979). Consequently, it
Daura Vega thanks the Spanish Ministry of Education and Science for her PhD Student Grant
(FPU).
Address correspondence to E. Pocurull Aixal`a, Department of Analytical Chemistry and Organic
Chemistry, University Rovira i Virgili, Carrer Marcell Domingo s/n, 43007 Tarragona, Spain. E-mail:
eva.pocurull@urv.net

D. Vega Moreno et al.

is very important to know the residual concentration of organochlorine pesticides in soils

after having been used for decades to study the intake of these pesticides in the harvest and
consequently in humans.
The techniques used for the extraction of organochlorine pesticides from soils are
Soxhlet extraction (Boer and Law, 2003), which requires high amounts of organic solvents
and long analysis time, ultrasonic extraction (Boer and Law, 2003), microwave assisted
solvent extraction (MASE) (Esteve-Turillas et al., 2004) and more recently pressurized
liquid extraction (PLE) (Hussen et al., 2006).
PLE is an extraction technique that combines elevated temperature and high pressure.
It represents a viable alternative to the conventional techniques such as soxhlet and ultrasonic extraction due to its lower organic solvent consumption and its lower extraction time
(Helaleh et al., 2005).
The aim of this work is to develop a method to determine thirteen organochlorine pesticides in agricultural soils using pressurized liquid extraction (PLE) and gas chromatography
with electron-capture detector (ECD) (Mwevura et al., 2002; Aguilar et al., 1999). Some
works have applied PLE to extract some organochlorine pesticides from soils; however,
none of them have applied PLE to a wide group of them. All samples were collected in
Ebros delta where organochlorine pesticides are used to mainly grow rice, although some
vegetables are also cultivated.

Materials and Methods

Materials
The organochlorine pesticides studied were: -hexachlorocyclohexane (HCH), -HCH, lindane ( -HCH), heptachlor, heptachlor-endo, -endosulfan, -endosulfan, aldrin, dieldrin,
endrin, p,p -DDD, p,p -DDE and p,p -DDT. All pesticides were purchased from Riedel-de
Haen (Seelze-Hannover, Germany) with a purity higher than 98% and were prepared by
dissolving appropriate amounts of the commercial products in hexane to obtain a concentration of 1 gL1 and stored in amber bottles at 4 C. Working solutions were prepared by
further diluting the initial concentrations with acetone. The internal standard was endosulfan
sulphate (99.9% purity), which was also supplied by Riedel-de Haen.
Hexane 99% of PAR quality (for pesticide analysis residue) was obtained from SDS
(Barcelona, Spain). Acetone for gas chromatography and aluminium oxide 90 active neutral
were supplied by Merck (Barcelona, Spain). The aluminium oxide was heated at 120 C in
the oven for 24 hours before its use. Dichloromethane, for pesticide residue analysis, was
obtained from Scharlau (Barcelona, Spain).
Helium (99.995% quality) and nitrogen (99.995% quality) were supplied by Carburos
Metalicos (Tarragona, Spain).
Instrumentation
Chromatographic analyses were performed on a Hewlett-Packard (HP, Palo Alto, CA, USA)
5890 Series II gas chromatograph equipped with a split/splitless injector, which was used
in the splitless mode and a 63 Ni electron-capture detector. A merlin microseal high-pressure
septum from Hewlett-Packard and a splitless liner were used. A Hewlett-Packard HP-5MS
(cross-linked 5%-phenyl-methylpolysiloxane) of 30 m 0.25 mm with a 0.25 m film
thickness was used to separate the analytes. Chromatographic data were recorded using the
HP CHEMSTATION.

Determination of Organochlorine Pesticides

The samples were extracted by PLE procedure using an ASE 200 accelerated solvent
extraction system (Dionex, Sunnyvale, CA, USA) equipped with an 11 ml stainless steel
extraction vessel.
Procedures
Sampling and Soil Pretreatment. Six agricultural soil samples were collected in Deltas
Ebro zone, in the mouth of the most important river in the northeast of Spain. Organochlorine
pesticides are used in this agricultural area to mainly grow rice. These samples were airdried at room temperature for more than 2 weeks, ground in a mortar with pestle, sieved
through a 125 m sieve and stored in the refrigerator at 4 C before analysis. The organic
matter contents of these soils were determined by the Sauerlandt method (organic matter
oxidation by potassium dichromate and sulphuric acid) (Sauerlandt and Berwecke, 1952).
Spiked soils were prepared by mixing with an organochlorine solution in acetone with
enough volume for covering all the sample to ensure homogeneity. After spiking, soils
were stirred to enable enough contact between compounds and matrix.
Pressurized Liquid Extraction. Soil samples were extracted using PLE procedure (Popp
et al., 1997; Zhuang et al., 2004). 5 g of the pre-treated soil were thoroughly mixed with
aluminium oxide and filled into 11 ml stainless steel extraction cell. Different solvent
mixtures of hexane, acetone and dichloromethane were studied as extractants in different
proportions, and hexane-acetone (1:1, v/v) was the optimum. The volume of the extraction
varies depending on the selected conditions during PLE procedure. The selected operating
conditions were as follows: extraction temperature, 50 C; extraction pressure, 1500 psi;
preheating period, 5 min; static extraction, 5 min; solvent flush, 60% of the cell volume;
nitrogen purge, 300 s; final extraction volume, 14.5 ml; and number of extraction cycles, 1.
The extract was filtered through a 0.45 m syringe-driven filter (Phenomenex,
Barcelona) and 10 ml were added, together with the internal standard, in a volumetric
flask before GC-ECD analysis. The volume of the internal standard added was considered
negligible.
Gas Chromatography Analysis with ECD Detection. 2 l of the PLE extract were injected
into GC by using a split/splitless injector heated at 250 C. The flow-rate of the carrier gas,
helium, was 2.8 ml min1 and nitrogen was used as make-up gas. The oven temperature
profile was as follows: the initial temperature was 60 C, which was increased to 160 C at
40 Cmin1 and then to 205 C at 1.8 Cmin1 . This temperature was held for 3 min. The
total run time was 30.5 min.

Results and Discussion

Optimization of PLE Extraction
A soil sample with 3.2% of organic matter content was used to optimize PLE parameters.
A blank chromatogram of this sample showed that no peaks eluted at the same retention
times as organochlorine pesticides.
Firstly, we optimized the extraction solvent by using 0.5 g of sample spiked at
700 gkg1 , 1 cycle, 100 C, 1500 psi, 5 min preheating time, 5 min static time, 60%
flush volume and 300 s purge time as initial conditions. Four different solvent mixtures
were tested: hexane-acetone (3:1, v/v), hexane-acetone (1:1, v/v), hexane-acetone (1:2,

D. Vega Moreno et al.

Table 1
Recoveries obtained for several extracting mixtures used in the PLE process. H= hexane, A= acetone, D= dichloromethane
Compound
-HCH
-HCH
-HCH
Heptachlor
Aldrin
Heptachlor-endo
-endosulfan
Dieldrin
p,p -DDE
Endrin
-endosulfan
p,p -DDD
p,p -DDT

HA
3:1

HA
1:1

HA
1:2

HD
1:1

90
88
22
51
92
73

95
130
68
22
76
60

57
79
68
111
93
86
27
101
111
99
48
114
121

19
104
29
77
99
105
7
117
131
117
65
120
86

36
65
42
9
64
6

13
83

95
52

(-): under detection limits of the method.

RSDs < 11%.

v/v) and hexane-dichloromethane (1:1, v/v). Recoveries were best when hexane-acetone
(1:1, v/v) was used (Table 1). In that case, recoveries higher than 68% were obtained for
all compounds except for -HCH, -endosulfan and -endosulfan, whose recoveries were
57%, 27% and 48%, respectively. To increase their recoveries, we optimized the number
of cycles by doing successive extractions to the same spiked sample. Recoveries from the
second cycle were negligible, thus we selected one cycle as the optimum.
Then, we considered the extraction temperature to be optimized. Three different temperatures were tested: 50 C, 75 C and 100 C. Figure 1 shows that higher recoveries were
obtained at 50 C for most of the analytes. Moreover, at this temperature less noisy baseline
was obtained because extraction of interferences was minimized. Also degradation process was avoided, especially for the most labile compounds such as -HCH and -HCH,
which are degraded to -HCH or p,p -DDD and p,p -DDT, which are degraded to p,p -DDE
(Walters and Aitken, 2001).
The extraction time or static time was also optimized. We determined the recoveries
obtained for 5 min, 10 min and 15 min. The results, shown in Figure 2, indicated that
5 min gave the best recoveries for the organochlorine pesticides under study. Recoveries
decreased with the extraction time because the interferences increased and consequently,
the determination was more difficult.
Flush volume was the next variable optimized and 60%, 100% and 150% of cell volume
were tested. Recoveries did not increase with a flush volume higher than 60%, thus it was
selected as the optimal. Then, pressure was optimized. For all compounds the recoveries
at 1000 psi were equal or lower than the recoveries with a pressure of 1500 psi. So, the
pressure was fixed at 1500 psi.
In order to decrease detection limits, we tested higher sample amounts. Up to 5 g gave
similar recoveries (see Table 2) than 0.5 g and no block of the extraction cell was observed. Therefore, it was selected for further experiments. Under these optimum extraction

Determination of Organochlorine Pesticides

Figure 1. Recoveries obtained by using different extraction temperatures in the PLE process.

conditions, good recoveries were obtained and minimum interferences were extracted, thus
a clean-up step could be avoided.
Method Validation
The same sample used for PLE optimization was used to validate the method (a soil with
3.2% organic matter content and without the analytes studied).
Linear range, calculated by internal standard calibration and doing direct injection, was
good for most compounds between 1 gL1 and 50 gL1 , with correlation coefficients
higher than 0.995. Adjusting for recovery efficiency, a concentration in soil about 3 gkg1

Figure 2. Recoveries obtained at different extraction times in the PLE process.

D. Vega Moreno et al.

Table 2
Validation data for the PLE/GC-ECD method developed
N

Compound

Recovery
(%)

RSD
(%)

1
2
3
4
5
6
7
8
9
10
11
12
13

-HCH
-HCH
-HCH
Heptachlor
Aldrin
Heptachlor-endo
-endosulfan
Dieldrin
p,p -DDE
Endrin
-endosulfan
p,p -DDD
p,p -DDT

100
74
64
98
89
81
77
98
95
99
80
99
103

8.4
7.5
5.7
5.4
2.9
1.8
11.0
7.1
4.8
4.9
5.2
8.9
7.4

LOD
(ngkg1 )
30
30
30
30
30
15
15
3
3
3
0.3
0.3
200

and 145 gkg1 , can be quantified. Limits of detection of the entire method were calculated
doing a signal noise ratio of 3 (Lindsay, 1992) and ranged between 0.3 and 200 ngkg1 .
Repeatability, expressed as relative standard deviation, RSD(%) (n= 4), was calculated for
a soil sample spiked with 70 gkg1 of each compound. RSDs were lower than 10% in
most cases. Results are shown in Table 2.
The chromatogram obtained for the mixture of pesticides extracted of spiked soil with
70 gkg1 is shown in Figure 3. It can be observed that the selected chromatographic
conditions allow a good separation of analytes and a short analysis time.
The influence of organic matter content on recoveries was studied (see Figure 4). Five
soils not contaminated with the compounds studied were spiked at 70 gkg1 (individual
concentration), a typical contamination level on agricultural soils (Kantachote et al., 2001),
and stored in the dark at room temperature for 24 hours before analysis. The organic matter
content was determined by Sauerlandt method and ranged from 0.6% to 11%. Recoveries
decreased with the organic matter content probably due to the interaction with humic substances present at higher concentration in soils with high organic matter content (Huang
et al., 2003). However, no linear relationship could be established between these two factors. Consequently, calibration by standard addition should be done when environmental
soil samples with different organic matter content are analyzed. As example, Figure 4 shows
the recoveries for 3 different soils. It can be observed that recoveries decrease about 15%
when organic matter content increases from 0.64% to 2.32% and they decreases more than
20% when organic matter content is 7.88%.
Finally, the method was validated by analyzing a certified reference soil (CRM814050). Because recoveries obtained with spiked samples may not be representative of those
found with native compounds, spiked analytes are generally lightly coated on the surface
of the matrix whereas native ones can be strongly adsorbed inside the matrix. This can
be explained by the diffusional and the kinetic limitations of the sorption process, and
the several interactions, which may have been simultaneously established between native
analytes and the matrix (Dupeyron et al., 1997).

Determination of Organochlorine Pesticides

Figure 3. Chromatogram of an extract of a spiked soil after PLE procedure. Chromatographic conditions as described in the text. The numbering refers to Table 2.

Due to the high concentration of the certified soil, 1 g was analyzed by the method developed. Table 3 reports the pesticides present in the certified soil and gives the corresponding
certificated values, the confidence intervals, the prediction intervals and the concentrations
found experimentally. All concentrations were between the prediction interval except for
-endosulfan, dieldrin, endrin and p,p -DDT.

Figure 4. Recoveries obtained for all compounds using 3 types of spiked soils with different organic
matter content.

D. Vega Moreno et al.

Table 3
Certified reference values and concentrations obtained by the method developeda

Compound
-HCH
-HCH
-HCH
Heptachlor
Aldrin
-endosulfan
Dieldrin
p,p -DDE
Endrin
endosulfa
p,p -DDD
p,p -DDT

Reference
Valueb

S.D.
(%)

Confidence
Interval

Prediction
Interval

Concentration
found

313
265
341
113
105
297
190
245
296
297
335
263

77.7
55.1
83.8
19.5
9.23
76.3
28.7
31.3
49.3
61.7
71.3
44.2

276350
234295
298384
102123
99.5110
260333
174206
227264
271322
265329
303368
241284

141485
142388
155527
69156
84125
128465
126254
175316
187406
160434
176494
165361

338 33.1
256 6.2
385 42.7
95 16.7
96 1.77
110 8.7
271 25.6
255 34.1
140 40.8
297 51.4
393 32.1
153 6.4

All values are expresed in gkg1

The pesticides values in the sample were certified by USEPA SW846 (3rd edition) method 8081A
(Pesticides by GC).
a

Then, the influence of aging time on recoveries was studied. Decreasing recoveries resulting from aging of matrices is a well-known phenomenon (Kiflom et al., 1999; Hawthorne
et al., 1999). The analytes present in recent soil samples are more easily extracted than those
that have had a longer contact time. This can be explained by how the analytes are incorporated by adsorption (short periods) (Dec and Bollag, 1997). The former phenomenon
occurs at the early stages of sorption, where H-bonding and Van der Waals forces prevail.
On the other hand, sequestration involves sorption at remote microsites within the soil
matrix (Kopinke et al., 1995).
In order to study the aging effect, we spiked a soil with 70 gkg1 and analyzed it at 24
hours, 1 week, 2 weeks and 6 weeks. A portion of this soil was stored at room temperature
in dark and another portion in the refrigerator at 4 C before extraction. Figure 5 shows the

Figure 5. Recoveries obtained with the aging time.

Determination of Organochlorine Pesticides

Table 4
Organochlorine pesticides found in analyzed soils (gkg1 )
Compound
HCH
HCH
Aldrin
endosulfan
Dieldrin
p,p -DDE
p,p -DDD
p,p -DDT

Soil 1

Soil 2

Soil 3

Soil 4

Soil 5

Soil 6

n.d.
40.6
n.d.
n.d.
n.d.
n.d.
n.d.
n.d.

n.d.
n.d.
n.d.
n.d.
n.d.
n.d.
n.d.
n.d.

0.7
n.d.
1.3
n.d.
15.0
8.1
n.d.
2.1

n.d.
n.d.
4.5
15.2
3.5
5.9
16.4
10.9

n.d.
n.d.
< loq
n.d.
15.3
10.3
n.d.
0.2

n.d.
n.d.
0.2
n.d.
< loq
n.d.
n.d.
n.d.

Loq: limit of quantification.

recoveries obtained for the different pesticides stored at room temperature with the aging
time.
It can be seen that recoveries decrease with the aging time for most of compounds,
which could be explained by the sorption process. It mainly occurs during the first week and
then recoveries keep almost constant. This can be the reason why recoveries of the certified
reference soil for some compounds are lower than the value expected. Recoveries for the
soil stored in the refrigerator showed the same behavior as room temperature samples but
with lower decrease of the recoveries.
Applications
The performance of the method was tested by analyzing 6 soils samples from the Ebros
Delta zone, where organochlorine pesticides are used for agricultural purposes. Pesticides

Figure 6. Chromatogram corresponding to soil 4 sample from Ebros Delta. The numbering refers
to Table 2.

10

D. Vega Moreno et al.

found are shown in Table 4. -HCH, heptachlor, heptachlor-endo, endrin and -endosulfan
were not found in any soil and the pesticides found in a higher number of samples were aldrin,
dieldrin, p,p -DDE and p,p -DDT, but at low g Kg1 levels. -HCH was the pesticide found
at higher concentration, 41 gkg1 , but it was only found in one soil. Figure 6 shows the
chromatogram corresponding to soil 4.

Conclusions
Thirteen organochlorine pesticides considered as priority pollutants by EPA have been extracted from soils using PLE procedure, with gas chromatography and electron-capture
detection after the establishment of the optimum conditions. The method developed represents a one step procedure, which allows the simple, fast and selective determination
of organochlorine pesticides in soils. Moreover, this method detects low concentrations of
organochlorine pesticides in soils up to 0.3 ngkg1 . The recoveries obtained and RSD have
been satisfactory. The method developed has demonstrated to be suitable for the extraction
of organochlorine pesticides in soils and provides a promising and viable alternative with
classical extraction techniques.

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