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Pesticides in the Distilled Spirits of Wine and Its Byproducts

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DOI: 10.1021/jf960457l

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2248 J. Agric. Food Chem. 1997, 45, 2248−2251

Pesticides in the Distilled Spirits of Wine and Its Byproducts

Paolo Cabras,*,† Alberto Angioni,† Vicenzo L. Garau,† Elizabeth V. Minelli,‡
Marinella Melis,† and Filippo M. Pirisi†
Dipartimento di Tossicologia, Università di Cagliari, viale Diaz 182, 09126 Cagliari, Italy, and
Departamento de Quı́mica Orgânica, Instituto de Quı́micasUNESP, Araraquara, SP, Brazil

The fate of eight fungicides (benalaxyl, fenarimol, iprodione, metalaxyl, myclobutanil, procymidone,
triadimefon, and vinclozolin) and five insecticides (dimethoate, fenthion, methidathion, parathion
methyl, and quinalphos) in wine and its byproducts (cake and lees) during the production of distilled
spirits was studied. Among the pesticides studied, only fenthion, quinalphos, and vinclozolin residues
were present in the distilled spirits. During wine distillation, respectively 13% and 5% of the initial
residues of fenthion and vinclozolin were transferred to the distilled spirit. Low percentages (2%
for fenthion and 0.1% for vinclozolin) of these active ingredients (AI) also passed from the lees to
the final-distilled spirit, when samples were fortified at 10.1 and 26.1 ppm for fenthion and
vinclozolin, respectively. Quinalphos passed only from the lees to the final-distilled spirit in
percentages lower than 1% when samples were fortified at the highest concentration (4.6 ppm).

Keywords: Pesticides; residues; distilled spirits

INTRODUCTION fate of pesticide residues during the distillation process

have been reported in the current literature. This paper
The fate of pesticide residues on grapes during wine-
aims to contribute to the knowledge of this issue.
making has been widely studied. The results of these
studies have been reported in some reviews (Cabras et
al., 1987; Flori and Cabras, 1990; Zironi et al., 1991; MATERIALS AND METHODS
Farris et al., 1992). In these papers is reported that Chemicals. The pesticides and anilazine were analytical
most of the pesticides remain adsorbed in the cake and standards purchased from Ehrenstorfer (Augsburg, Germany).
lees, which are byproducts of wine-making, at relevant Triphenylphosphate (99%) was of analytical grade (Janssen,
levels, and are transferred to the wine in low percent- Geel, Belgium). Acetone, acetonitrile and benzene were HPLC
ages. Only a few active ingredients (benalaxyl, di- grade solvents (Carlo Erba, Milano, Italy), while petroleum
methoate, and fenthion) are completely transferred from ether and n-hexane (Carlo Erba) were special reagents for
pesticide determination. Cyclohexane and ethyl alcohol were
the grapes to the wine (Cabras et al., 1991, 1994, 1995). analytical grade solvents (Carlo Erba). Anhydrous sodium
Therefore, the cake and lees contain most of the sulfate and sodium chloride were of analytical grade (Carlo
pesticide residues present on grapes. These byproducts Erba). Stock standard solutions were prepared in absolute
are used in industry to produce alcohol and distilled ethyl alcohol. Working standard solutions were obtained by
beverage spirits. Since about 17 kg of cake with an dilution with acetone/petroleum ether (50/50, v/v) containing
average of 4.5% alcohol content is obtained from 100 triphenylphosphate as internal standard (IS) at 0.3 ppm for
kg of grapes (Garoglio, 1973), 2220 kg of cake is GC-NPD determinations, or n-hexane containing anilazine as
necessary to obtain 100 L of alcohol. If the pesticide the internal standard at 0.5 ppm for GC-ECD determinations
residues present in grapes were to pass completely from and with an acetonitrile/water mixture (50/50, v/v) for HPLC
determinations.
the grapes to the cake, and from the latter to the alcohol,
Distillation Process. Wine. 200 mL of wine, at 12%
their residue levels would be 130 times higher than in alcohol (v/v), were distilled by using the Jaulmes apparatus
grapes. Also, 140 kg of grapes produces approximately (Lequeax, Paris). A fraction of 50 mL at 43.9% alcohol (v/v)
1 hL of wine, which gives 5.5 kg of liquid lees at 4.5% was collected. Four of these fractions were redistilled together,
alcohol content (Garoglio, 1973). If all pesticide residues and a second 50 mL fraction at 83% alcohol was collected.
were to be transferred from the grapes to the lees and Lees. 200 g of liquid lees at 11% of solid content and 10.1%
from the lees to the alcohol, their residue levels would of alcohol was distilled as described for wine. The first and
be 574 times higher than in grapes. Even wine is second fractions collected had 29% and 76% alcohol, respec-
submitted to distillation to produce alcohol and brandy, tively.
but in this case if all residues were to be transferred to Cake. 200 g of cake at 11.3% of alcohol was distilled using
the Camboni apparatus, and a 50 mL fraction at 32.5% of
alcohol, as wine contains ca. 10% (v/v) of alcohol, they
alcohol was collected. This fraction was redistilled by the same
would be ca. 10 times concentrated. These theoretical procedure described for wine and lees, and a second fraction
concentration factors indicate that distilled spirits, at 82% alcohol (v/v) was collected.
which are used to produce alcoholic beverages such as Apparatus. Distillation. Alcohol was stripped from wine
brandy, cognac, and grappa, would have a toxic potential and lees by a Jaulmes apparatus (described in Ribereau-Gayon
if the technological process did not contribute to de- et al., 1976), while a Camboni apparatus (described in
crease pesticide residues considerably. Despite the Garoglio, 1973) was used for cake. These spirits were redis-
potential toxic risks presented by the distilled spirits tilled with a Jaulmes apparatus.
of wine and its byproducts, no studies concerning the Chromatography. A gas chromatograph HRGC Mega 5160
(Carlo Erba, Milano, Italy) was employed, fitted with an N-40
nitrogen-phosphorus detector, an ECD 400 detector, an AS
* Corresponding author (fax +39 70 300740). 550 autosampler (Carlo Erba), and a split-splitless injector,
† Università di Cagliari.
connected to an HP 3396-A reporting integrator (Hewlett-
‡ Instituto de Quı́micasUNESP. Packard, Avondale, PA).

S0021-8561(96)00457-8 CCC: $14.00 © 1997 American Chemical Society

Pesticides in Distilled Wine Spirits J. Agric. Food Chem., Vol. 45, No. 6, 1997 2249

An HP model 1050 liquid chromatograph (Hewlett-Packard) mixture (50:50, v/v) was used at the flow rate of 1 mL/
was used. It consisted of a pump, an autosampler with a 100 min, and the wavelength was 200 nm. Quantitative
µL loop, and a variable-wavelength UV/vis detector. The determinations were performed by the external stan-
chromatograph was connected to an HP 3394 reporting dard method by measuring peak heights vs concentra-
integrator (Hewlett-Packard).
tions. Good linearities were achieved in the range 0.01-
1.5 ppm, with correlation coefficients between 0.9999
RESIDUE ANALYSIS and 1.
GC-NPD Determination: Dimethoate, Fenthion, Under the operating conditions of different methods,
Methidathion, Parathion Methyl, and Quinalphos. the limits of detection ranged between 0.001 and 0.003
Extraction Procedure. A 5 mL aliquot of the distilled mg/kg for the studied compounds.
spirit was transferred to a screw-capped 30 mL test Recovery Assays. Untreated distilled samples were
tube; 2 g of sodium chloride and 10 mL of an acetone/ fortified with pesticide and processed according to the
petroleum ether mixture (1:1, v/v) containing triph- above procedure. Recovery assays, carried out at 3.5,
enylphosphate as the internal standard (IS) were added, 1.5, 0.3, and 0.05 ppm, showed values ranging between
and the flask was agitated in a rotating stirrer for 15 86% and 115% with a maximum CV of 11%.
min. The phases were allowed to separate, and the
organic layer was poured into another flask containing
RESULTS AND DISCUSSION
2 g of anhydrous sodium sulfate and then injected for
GC analysis.
In this work thirteen pesticides among the active
GC Analysis. A Durabond fused silica column (30 m
ingredients commonly used for controlling the parasites
× 0.25 mm i.d.) (J&W Scientific, Folsom, CA) was
of grapes were studied. The study was carried out
employed, with a DB 1701 liquid phase (14% cyanopro-
fortifying the wine, cake, and lees samples with the
pylphenylmethylpolysiloxane, film thickness 0.25 µm).
pesticides at different concentrations. Fortification
The injector and detector were operated at 250 and 290
levels were selected according to the maximum residue
°C, respectively. The sample (2 µL) was injected in the
limits (MRL) established for grapes in Italy. The
splitless mode (60 s), and the oven temperature pro-
behavior of the residues was evaluated at the selected
grammed as follows: 90 °C for 1 min, raised to 180 °C
concentrations and at concentrations ten times lower.
(20 °C/min) and held for 1 min, and then raised to 280
On the lees and cake samples, experiments were also
°C (5 °C/min) and held for 4 min. Helium was the
performed at average levels 21 and 5 times higher than
carrier and make-up gas at 120 and 130 kPa, respec-
MRL, respectively. In industry to produce brandy or
tively. Calibration graphs were constructed with the
grappa, wine and its byproducts are usually submitted
internal standard (IS) method by measuring peak
to a first distillation in a stripping column, which
heights vs concentrations. Good linearities were achieved
produces a spirit at ca. 30% of alcohol, followed by a
in the range 0.01-3.0 ppm, with correlation coefficients
second distillation in a rectifying column, to give a spirit
between 0.9991 and 0.9995.
at ca. 80% (De Rosa and Castagner, 1994). In our
GC-ECD Determination: Procymidone and Vin- experiments we tried to reproduce the same scheme, by
clozolin. Procedure. A 100 µL aliquot of the distilled producing two distilled spirits at alcoholic contents
spirit was transferred to a 300 µL vial, evaporated to similar to those in the industrial process and determin-
dryness under a nitrogen stream, taken up with 100 µL ing the pesticide residues in both. The results obtained
of n-hexane containing anilazine as is at 0.5 ppm, and in these experiments are reported in Tables 1 and 2.
injected for GC analysis.
The residues of fenarimol, methidathion, and my-
GC Analysis. A Durabond fused silica column (30 m
clobutanil present in the wine, lees, and cake samples
× 0.25 mm i.d.) (J&W Scientific, Folsom, CA) was
at the studied concentrations did not pass to the distilled
employed, with a DB 5 liquid phase (5% phenylmeth-
spirits.
ylpolysiloxane, film thickness 0.25 µm). The sample (1
µL) was injected in the split mode (1:20), and the oven Benalaxyl residues were found in first-distilled spirits
temperature programmed as follows: 150 °C for 1 min obtained from the lees and cake fortified at the highest
and then raised to 250 °C (10 °C/min) and held for 2 concentrations (30.7 and 7.7 ppm, respectively). In both
min. Helium was the carrier gas at 100 kPa, and distilled spirits the residue amount was the same (0.06
nitrogen was the make-up gas at 150 kPa. Calibration ppm), which is 0.2% and 0.8% of the residues present
graphs were constructed with the internal standard in the lees and cake, respectively. No residue was found
method by measuring peak heights vs concentrations. in the final-distilled spirits of wine, lees, and cake at
Good linearities were achieved in the range 0.01-3.0 the studied concentrations.
ppm, with correlation coefficients of 0.9992 and 0.9998. The behavior of iprodione was similar to that of
HPLC Determination: Benalaxyl, Fenarimol, benalaxyl. In the first-distilled spirits that were ob-
Iprodione, Metalaxyl, Myclobutanil, and Triadime- tained from lees and cake fortified at 19.2 and 11.8 ppm,
fon. Procedure. A 1 mL aliquot of distilled spirit was respectively, 0.08 and 0.03 ppm of this fungicide were
transferred to an 8 mL vial, 2 mL of a cyclohexane/ found. These amounts represented 0.4% and 0.3% of
benzene mixture (1:1, v/v) was added, and the flask was the initial residue. No residue was found in any of the
agitated in a rotating stirrer for 10 min. The phases final-distilled spirits.
were allowed to separate, and 1 mL of the upper layer Metalaxyl residues only passed to the first-distilled
was transferred to a 1.8 mL vial. The solvent was spirit when this was obtained from cake fortified at the
evaporated to dryness under a nitrogen stream, taken highest concentration. From a initial residue of 10.97
up with 0.5 mL of an acetonitrile/water mixture (50/50, ppm, 0.03 ppm (0.3%) was obtained. No residue was
v/v), and injected for HPLC analysis. found in any of the final-distilled spirits.
HPLC Analysis. A Spherisorb S5-C8 column (250 × Procymidone residues were found in the first-distilled
4.6 mm i.d., 5 µm) (Phase Separations, Waddinxveen, spirits of wine and lees but not in those of cake. The
Netherlands) was employed. An acetonitrile/water residue percentages found in the distilled spirits were
2250 J. Agric. Food Chem., Vol. 45, No. 6, 1997 Cabras et al.

Table 1. Residues (mg/kg ( sd) of Fungicides in the Distilled Spirits of Wine and Its Byproducts
fungicide sample concn 1st distn. 2nd dist. fungicide sample concn 1st dist. 2nd dist.
benalaxyl wine 1.16 n.d.a n.d. myclobutanil wine 0.48 n.d. n.d.
0.15 n.d. n.d. 0.06 n.d. n.d.
lees 30.7 0.06 ( 0.01 n.d. lees 12.6 n.d. n.d.
1.16 n.d. n.d. 0.48 n.d. n.d.
0.15 n.d. n.d. 0.06 n.d. n.d.
cake 7.7 0.06 ( 0.06 n.d. cake 2.5 n.d. n.d.
1.16 n.d. n.d. 0.48 n.d. n.d.
0.15 n.d. n.d. 0.06 n.d. n.d.
fenarimol wine 0.34 n.d. n.d. procymidone wine 1.25 0.17 ( 0.01 n.d.
0.04 n.d. n.d. 0.17 0.02 ( 0.0 n.d.
lees 6.1 n.d. n.d. lees 24.3 1.39 ( 0.21 n.d.
0.34 n.d. n.d. 1.25 0.08 ( 0.03 n.d.
0.04 n.d. n.d. 0.17 n.d. n.d.
cake 1.6 n.d. n.d. cake 4.86 n.d. n.d.
0.34 n.d. n.d. 1.25 n.d. n.d.
0.04 n.d. n.d. 0.17 n.d. n.d.
iprodione wine 2.44 n.d. n.d. triadimefon wine 1.58 n.d. n.d.
0.31 n.d. n.d. 0.2 n.d. n.d.
lees 19.2 0.08 ( 0.01 n.d. lees 45.3 1.13 ( 0.14 n.d.
2.44 n.d. n.d. 1.58 n.d. n.d.
0.31 n.d. n.d. 0.2 n.d. n.d.
cake 11.8 0.03 ( 0.01 n.d. cake 9.06 n.d. n.d.
2.44 n.d. n.d. 1.58 n.d. n.d.
0.31 n.d. n.d. 0.2 n.d. n.d.
metalaxyl wine 2.2 n.d. n.d. vinclozolin wine 1.6 3.16 ( 0.85 0.08 ( 0.03
0.27 n.d. n.d. 0.2 0.83 ( 0.27 n.d.
lees 41.2 n.d. n.d. lees 26.1 2.09 ( 0.10 0.03 ( 0.01
2.2 n.d. n.d. 1.6 0.42 ( 0.18 n.d.
0.27 n.d. n.d. 0.2 n.d. n.d.
cake 10.97 0.03 ( 0.01 n.d. cake 6.5 0.63 ( 0.21 n.d.
2.2 n.d. n.d. 1.6 0.43 ( 0.05 n.d.
0.27 n.d. n.d. 0.2 0.12 ( 0.14 n.d.
a
n.d. ) not detectable.

Table 2. Residues (mg/kg ( sd) of Insecticides in the Distilled Spirits of Wine and Its Byproducts
insecticide sample concn 1st dist. insecticide sample concn 1st dist. 2nd dist.
dimethoate wine 1.03 n.d.a n.d. parathion methyl wine 0.25 0.05 ( 0.0 n.d.
0.13 n.d. n.d. 0.03 n.d. n.d.
lees 24.9 0.02 ( 0.01 n.d. lees 5.0 0.51 ( 0.02 n.d.
1.03 n.d. n.d. 0.25 0.04 ( 0.0 n.d.
0.13 n.d. n.d. 0.03 n.d. n.d.
cake 4.90 n.d. n.d. cake 1.00 0.03 ( 0.02 n.d.
1.03 n.d. n.d. 0.25 n.d. n.d.
0.13 n.d. n.d. 0.03 n.d. n.d.
fenthion wine 0.62 0.71 ( 0.06 0.08 ( 0.02 quinalphos wine 0.25 0.11 ( 0.0 n.d.
0.08 0.13 ( 0.02 n.d. 0.03 0.02 ( 0.0 n.d.
lees 10.1 2.82 ( 0.5 0.19 ( 0.03 lees 4.6 0.48 ( 0.06 0.04 ( 0.01
0.62 0.20 ( 0.02 n.d. 0.25 0.04 ( 0.0 n.d.
0.08 0.05 ( 0.0 n.d. 0.03 n.d. n.d.
cake 2.50 0.07 ( 0.05 n.d. cake 1.00 n.d. n.d.
0.62 0.03 ( 0.02 n.d. 0.25 n.d. n.d.
0.08 <0.01 n.d. 0.03 n.d. n.d.
methidathion wine 0.20 n.d. n.d.
0.03 n.d. n.d.
lees 4.90 n.d. n.d.
0.20 n.d. n.d.
0.03 n.d. n.d.
cake 1.00 n.d. n.d.
0.03 n.d. n.d.
a n.d. ) not detectable.

12% for wine and 6% for lees. No residue was found in In wine-distilled spirits, this AI was found respectively
any of the final-distilled spirits. at concentrations of two and four times the initial
For triadimefon, residues were found only in the first- residue present in the samples fortified at the highest
distilled spirit obtained from lees fortified with 45.3 and lowest levels. Considering that in the first-distilled
ppm. The amount present in the first-distilled spirit spirit the alcoholic content is about four times higher
represented 2.4% of the initial residue. No residue was than that of wine, this means that vinclozolin residues
found in any of the final-distilled spirits. passed completely from wine to the distilled spirit at
Dimethoate showed a similar behavior to that of the lowest concentration, while at the highest concen-
triadimefon. This AI passed only from lees fortified with tration only 50% passed.
24.9 ppm to the first-distilled spirit at a percentage
lower than 0.1%. Lees behaved in the same way as cake, but their
In the first-distilled spirit, vinclozolin, presented the behavior was very different from that of wine. At the
highest amount of residue among the pesticides studied. highest concentrations, ca. 9% of the initial residue was
 Pesticides in Distilled Wine Spirits J. Agric. Food Chem., Vol. 45, No. 6, 1997 2251

transferred to the first-distilled spirit and this percent- to the distilled spirit. These AI were also transferred
age increased on decreasing the concentration. to the final-distilled spirit obtained from lees but only
Residues of vinclozolin were found in the final- when the initial concentration was very high and at low
distilled spirit only when the initial residue in the first- percentages (2% and 0.1% for fenthion and vinclozolin
distilled spirit was higher than 2 ppm. They were ca. at 10.1 and 26.1 ppm, respectively). Quinalphos resi-
2% of the residue found in the first-distilled spirit. The dues pass from lees to the distilled spirit at lower than
residue levels found in the final-distilled spirits repre- 1% and only when at the highest concentration (4.6
sented 5% and 0.1% of the initial residues in wine and ppm).
lees, respectively. The remarkable decrease in residues during the
Fenthion showed an analogous behavior to that rectifying process could depend on fact that very low
observed for vinclozolin. The residue in the first wine- amounts of residue are transported by alcoholic vapors
distilled spirit were higher than those in wine. The while higher amounts are transported by water vapors.
concentration factors of the distilled spirits were 1.1 and Consequently we should expect that distilled spirits of
1.6, respectively, for the highest and lowest levels of an alcoholic content of 95-96% would give lower residue
wine. Subsequent distillation in the rectifying column concentrations. The highest residue concentrations
determined a remarkable residue decrease in the final- used in our experiments are not expected to occur in
distilled spirit (0.08 ppm). This represented 13% of the industrial practice. In fact, it is supposed that the
initial residue of fenthion. product submitted to a distillation process in industry
The results obtained for lees distillation showed that is made up of several batches containing different AI.
as the initial concentration of fenthion decreased, the This would dilute the residue concentrations. It is
percentage of residues transferred to the first-distilled assumed, therefore, that the distilled spirits produced
spirit increased (28%, 32%, 63% for concentrations of in industrial systems should be free from residues of
10.1, 0.62, and 0.08 ppm, respectively). After the second the studied pesticides.
distillation, the residue found in the final-distilled spirit
was 0.19 ppm. This amount represented 7% and 2% of LITERATURE CITED
the initial residues in the first-distilled spirit and lees Cabras, P.; Meloni, M.; Pirisi, F. M. Pesticide fate from vine
respectively. to wine. Rev. Environ. Contam. Toxicol. 1987, 99, 83-117.
A low percentage of residue was transferred from the Cabras, P.; Porcu, M.; Spanedda, L.; Cabitza, F. The fate of
cake to the first-distilled spirit (3% and 5% for the the fungicide benalaxyl from vine to wine. Ital. J. Food Sci.
1991, 3, 181-186.
highest and intermediate concentrations, respectively).
Cabras, P.; Garau, V. L.; Melis, M.; Pirisi, F. M.; Cubeddu,
No residue was found in any of the final-distilled spirits M.; Cabitza, F. Pesticide residues of dimethoate and chlo-
from cake. rpyrifos in grapes and wine. Proc. Giornate Fitopatologiche
Quinalphos showed the same behavior as fenthion. 1994, 1, 27-32.
On decreasing the initial concentration of wine, the Cabras, P.; Garau, V. L.; Pirisi, F. M.; Cubeddu, M.; Cabitza,
percentage of residues transferred to the first-distilled F.; Spanedda, L. Fate of some insecticides from vine to wine.
spirit increased (44% and 67% for concentrations of 0.25 J. Agric. Food Chem. 1995, 43, 2613-2615.
and 0.02 ppm, respectively). An analogous behavior was De Rosa, T .; Castagner, R. Tecnologia delle grappe e dei
observed with lees, but the percentage values were distillati d’uva; Edagricole: Bologna, Italy, 1994; pp 176-
lower (10% and 16%). Residues were found only in the 179.
Farris, G. A.; Cabras, P.; Spanedda, L. Pesticide residues in
final-distilled spirit obtained from lees at 4.6 ppm. The food processing. Ital. J. Food Sci. 1992, 3, 149-169.
amount present in this distilled spirit (0.04 ppm) was Flori, P.; Cabras, P. Pesticide residues in wine. Vignevini 1990,
8% of the residue in the first-distilled spirit, i.e., less 17 (7-8), 31-37.
than 1% of the initial residue. Garoglio P. G. Enciclopedia Vitivinicola Mondiale; Ed. Sci.
Residues of parathion methyl were found in the first- U.I.V.: 1973, Vol. 8, pp 61-66, 75.
distilled spirits obtained from wine, lees, and cake. The Ribereau-Gayon, J.; Peynaud, E.; Ribereau-Gayon, P.; Sudraud,
residue amounts represented 20%, 10%, and 3% of the P. In Sciences et techniques du vin. Vol. 1. Analyse et controle
initial concentrations in wine, lees, and cake, respec- des vins; Dunod: Paris, 1976, pp 51-58.
tively. No residue was found in any of the final-distilled Zironi, R.; Farris, G. A.; Cabras, P.; Fatichenti, F. Pesticide
residues from vine to wine. Atti. Accad. Ital. Vite Vino, Siena
spirits.
1991, 43, 351-369.
CONCLUSIONS Received for review June 24, 1996. Revised manuscript
Samples of wine, lees, and cake containing residues received March 3, 1997. Accepted March 5, 1997.X E.V.M.
of the 13 studied pesticides yielded distilled spirits that acknowledges the CNPqsBrasil for a fellowship.
were practically free of pesticide residues. During the JF960457L
distillation process, only quinalphos, fenthion, and
vinclozolin were transferred to the final-distilled spirit. X Abstract published in Advance ACS Abstracts, May
13% of fenthion and 5% of vinclozolin passed from wine 1, 1997.

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