ARTICLE IN PRESS

Journal of Stored Products Research 41 (2005) 91–102

Bioactivities of cymol and essential oils of Cupressus

sempervirens and Eucalyptus saligna against Sitophilus zeamais
Motschulsky and Tribolium confusum du Val
A.L. Tapondjoua,*, C. Adlerb, D.A. Fontemc, H. Boudaa, C. Reichmuthb
a
Laboratory of Environmental and Applied Chemistry, Faculty of Science, University of P.O. Box 183,
Dschang, Cameroon
b
Federal Biological Research Centre for Agriculture and Forestry, Institute for Stored Protection, Konigin-Luise-Str 19,
Berlin D-14195, Germany
c
Department of Plant Protection, Faculty of Agricultures, University of Dschang, P.O. Box 208, Dschang, Cameroon
Accepted 12 January 2004

Abstract

The essential oils extracted from Eucalyptus saligna and Cupressus sempervirens leaves were analysed by
GC-MS and evaluated along with cymol, one of their main constituents for their repellent and toxic effects
on Sitophilus zeamais and Tribolium confusum. Contact toxicity assayed by impregnation on filter paper
discs or coating onto maize grains showed that these chemicals caused significant mortality of the test
insects. Eucalyptus oil was more toxic than Cupressus oil to both insect species (LD50=0.36 ml/cm2 for
S. zeamais and 0.48 ml/cm2 for T. confusum) on filter paper discs, and was more toxic to S. zeamais on
maize (LD50=38.05 ml/40 g grain). Both oils considerably reduced the F1 progeny production and grain
weight loss. Moreover, both crude oil extracts produced a stronger repellent activity against the test insects
than did cymol. These results suggest that the essential oils from E. saligna and C. sempervirens may be used
in grain storage against insect pests.
r 2004 Elsevier Ltd. All rights reserved.

Keywords: Eucalyptus saligna; Cupressus sempervirens; Essential oil; Cymol; Sitophilus zeamais; Tribolium confusum;
Repellency; Contact toxicity

*Corresponding author. Tel.: 237-345-20-91; fax: 237-345-12-02.

E-mail address: tapondjou2001@yahoo.fr (A.L. Tapondjou).

0022-474X/$ - see front matter r 2004 Elsevier Ltd. All rights reserved.
doi:10.1016/j.jspr.2004.01.004
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92 A.L. Tapondjou et al. / Journal of Stored Products Research 41 (2005) 91–102

1. Introduction

Concerns over health and environmental problems associated with synthetic insecticides
currently in use in agriculture have led to an intensification of efforts to find safe, effective and
viable alternatives. In this regard plant-based insecticides (PBIs) as described by Rosenthal (1986)
can be less toxic to man, readily biodegradable, suitable for use by small scale farmers and yet
capable of protecting crops from attack by a wide range of insect pests.
Plant products have for many generations been used by small scale farmers in parts of Africa to
protect stored products from insect infestation (Hassanali et al., 1990; Poswal and Akpa, 1991;
Baba Tierto, 1994; Parh et al., 1998). Protection of stored products generally involves mixing
grains with protectants made up of plant materials.
Many African plants are potential sources of pesticides and have been shown to contain either
antifeedant, repellent or insecticidal compounds that enable the crude plant material or an
extracted active compound to protect stored products (Kubo and Nakanishi, 1977; Olaifa et al.,
1987; Hassanali et al., 1990; Bekele et al., 1996; Bouda et al., 2001).
As part of this investigation, a survey of ethnobotanical materials used for stored-product
protection in the Western highlands of Cameroon was started with the objective of evaluating
their efficacy and identifying their active secondary metabolites. Two plant materials form the
subject of this paper: the leaves of Cupressus sempervirens L. (Cupressaceae) and those of
Eucalyptus saligna Sm. (Myrtaceae). These are two aromatic plants mainly used in local storage
structures by communities of the Western highlands of Cameroon to protect their stored grains
from insect infestation (Tapondjou et al., 2000). Their dried leafy branches emit strong persistent
aromatic odours for long periods of time, indicating their high volatile oil content.
This paper describes the chromatographic examination of the volatile oils extracted from these
plant materials as well as bioassays for evaluating their contact toxicity and repellency effects
against the maize grain weevil, Sitophilus zeamais Motschulsky and the red flour beetle, Tribolium
confusum du Val. In view of the growing interest in assessing the individual activity of major
components of essential oils, the above bioassays were also carried out with cymol ( p-cymene),
one of the constituents of the essential oils of both plants.

2. Materials and methods

2.1. Plant materials

The leaves of C. sempervirens and E. saligna were collected in April 1999 from Dschang located
in the Menoua Division of the Western highlands of Cameroon. The identity of both plants was
confirmed by the Plant Biology Department of the University of Dschang.

2.2. Isolation and characterisation procedure of the essential oils

The plant materials were dried for 3 days at room temperature and ground to powder before
being subjected to hydrodistillation using a modified Clevenger apparatus for 6 h. Oils collected
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A.L. Tapondjou et al. / Journal of Stored Products Research 41 (2005) 91–102 93

were dried over anhydrous sodium sulphate, filtered and weighed yielding 1% (w/w) of pale
yellow oil for C. sempervirens and 0.9% for E. saligna.
Analysis of the essential oils was carried out by GC-MS on a HP 5890 II gas chromatograph
coupled to a HP 5972 mass selective spectrometer using a DB wax fused silica capillary column
(60 m x 0.25 mm i.d. 0.25 mm film thickness). GC conditions: the oven was programmed to rise
from 60–220
C at a rate of 5
C/min using helium as carrier gas. The flow rate was 0.9 ml/min, the
injector temperature 230
C, the interphase temperature 240
C and the mass range up to
650 a.m.u. Cymol (p-cymene) (99.5% purity) used for bioassays was purchased from Fluka
Chemicals, Germany.

2.3. Insects

Sitophilus zeamais and T. confusum were cultured in a controlled temperature and humidity
chamber (2571
C and 70–75% rh) in darkness. Parent adults were obtained from laboratory
stock cultures maintained at the Institute for Stored Product Protection, Berlin, Germany. The
food media used were whole maize grains for S. zeamais, and wheat feed and rolled oats for T.
confusum.

2.4. Contact toxicity on filter paper

The contact effect of both crude oils and cymol against both insect pests was evaluated on filter
paper discs (Whatman N
1) (7 cm diameter, surface 38.5 cm2) which were treated with the
substances diluted in acetone. The filter papers were placed in glass Petri dishes (7 cm diameter).
An aliquot of 0, 7.5, 15, 30 and 60 ml of each oil or 0, 30, 40 and 50 ml of cymol diluted in 1 ml of
acetone was applied to the filter paper discs corresponding to dosages of 0, 0.19, 0.39, 0.78 and
1.56 ml/cm2 for the essential oils and 0, 0.78, 1.04 and 1.30 ml/cm2 for cymol. The acetone was
allowed to evaporate for 10 min prior to the introduction of 20 unsexed adults (3–7 days old) of
each insect species separately into each dish and these were kept in darkness in the laboratory at
2571
C and 70–75% rh. Each treatment was replicated four times. Insect mortalities were
recorded daily up to 5 days. Percentage insect mortality was calculated using the Abbott
correction formula for natural mortality in untreated controls (Abbott, 1925).

2.5. Contact toxicity of essential oils to S: zeamais; F1 progeny production and weight loss in maize
grains

The effect of the crude oils-treated-maize grains on adult mortality of S. zeamais was studied in
the laboratory at 2571
C and 70–75% rh in darkness. The grains were treated separately with
solutions of 0, 50, 75 or 100 ml of essential oils in 1 ml acetone. Test solutions were mixed with 40 g
samples of grain in 380-ml glass jars and stirred continuously for 10 min with a rotary shaker
(Multifix GmbH, Germany) to ensure even spread of the materials over the surface of the grains.
Samples were kept for 20 min to allow the solvent to evaporate completely. The grains were then
infested with twenty 3–7-day-old adults of S. zeamais per jar and each jar was covered with a
nylon mesh held in place with rubber bands. Each set of treatments was repeated four times and
the number of dead insects in each jar was counted daily. Percentage mortality was calculated
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94 A.L. Tapondjou et al. / Journal of Stored Products Research 41 (2005) 91–102

using the Abbott formula. Thereafter the remaining living adults were removed and the different
jars containing grains were kept under the same experimental conditions until the F1 progeny
adults emerged. Based on the life cycle of the untreated insects, the counting period of F1 was
established so as to avoid an overlap of population generations.
The percentage reductions in adult emergence or inhibition rates (IR) were calculated using the
following formula:

Cn  Tn
IRð%Þ ¼ 100;
Cn

where Cn is the number of insects in the control jar and Tn the number of insects in the treated jar.
After counting the number of F1 in each jar the damaged grains were sieved to remove the frass,
and then weighed to assess their weight loss.

2.6. Lethal doses assessment

The different 50% and 95% lethal doses were calculated using probit analysis (Finney, 1971) in
which probit-transformed percentage mortalities were regressed on log dose.

2.7. Repellency bioassay

The repellent effects of the different phytochemicals against S. zeamais and T. confusum were
evaluated using the area preference method (McDonald et al., 1970). Test areas consisted of 7 cm
Whatman N
1 filter paper cut in half (19.25 cm2). Test solutions were prepared by diluting 1, 2, 4
and 8 ml of each essential oil or cymol in 0.5 ml acetone. Each solution was uniformly applied to a
half-filter paper disc using a micropipette corresponding to the doses of 0.05, 0.10, 0.20 and
0.40 ml/cm2. The other half filter paper was treated with acetone alone and used as control.
Chemically treated and control half discs were air-dried for 10 min to evaporate the solvent
completely. Full discs were subsequently remade by attaching treated halves to untreated halves
with clear adhesive tape. Each remade filter paper disc was placed into a 7 cm Petri dish and 20
unsexed adult insects of each species were released separately at the centre of the filter paper disc
and the Petri dishes were subsequently covered. The treatments were replicated 5 times and the
numbers of insects present on the control (Nc) and treated (Nt) areas of the discs were recorded
after 2 h.
Percentage repellency (PR) values were computed as follows:

PR ¼ ½ðNc  Nt Þ=ðNc þ Nt Þ100:

The mean repellency value of each phytochemical was calculated and assigned to repellency
classes (Juliana and Su, 1983) from 0 to V: class 0 (PR o 0.1%), class I (PR=0.1–20%), class II
(PR=20.1–40%), class III (40.1–60%), class IV (60.1–80%), class V (80.1–100%).
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3. Results

3.1. Chemical constituents of the essential oils

The volatile constituents of the different oils were identified by their retention index and mass
spectrum in comparison with those of standard synthetic compounds. The results of the chemical
analysis are presented in Table 1. These results revealed that the oil from C. sempervirens is mainly
constituted of mono-and sesquiterpenoids with the most important constituents identified as a-
pinene (9.9%), terpinen-4-ol (11.2%) and sabinene (14.8%) whereas Eucalyptus oil is mainly
constituted of a-pinene (39.47%) and cymol (31.1%).

3.2. Filter paper contact toxicity

The percentage mortalities of each insect species after 5 days exposure to increasing dosages of
volatile oils from C. sempervirens and E. saligna on filter paper discs are shown in Figs. 1–4.
Mortality of S. zeamais was almost nil at low concentrations of the essential oil during the first
two days after treatment but increased rapidly thereafter. The doses of 0.78 and 1.56 ml/cm2 of
each oil were able to induce 100% mortality of insects within 5 days of exposure (Figs. 1 and 2).
Moreover, both oils induced significant mortality of T. confusum within the exposure period and
total mortality was achieved with the doses of 0.78 and 1.56 ml/cm2 within 4 days (Figs. 3 and 4).

Table 1
Chemical constituents of the essential oils from E. saligna and C. sempervirens leaves collected from the Western
highlands of Cameroon
Compound % composition
C. sempervirens E. saligna
a-Pinene 9.9 39.5
Sabinene 14.8 —
D3-Carene 4.2 —
Myrcene 2.3 —
a-Terpinene 4.2 —
Limonene 3.9 2.1
b-Phellandrene 1.5 —
1,8-Cineol — 9.8
Terpinene 5.7 9.5
p-Cymene (cymol) 3.8 31.1
Terpineolene 2.4 —
Terpinen-4-ol 11.4 0.6
Bicyclosesquiphellandrene 2.3 —
Terpineol 2.7 3.7
a-Terpinyl acetate 3.3 —
Eucumene 1.4 —
Cis calamenene 1.7 —
d-Cadinene 1.9 —
Carvacrol — 1.7
Cedrol 3.3 —
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100

80

% mortality
60
0µl/cm2
40 0.19µl/cm2
0.39µl/cm2
20 0.78µl/cm2
1.56µl/cm2
0
0 1 2 3 4 5
Exposure time(days)

Fig. 1. Percentage mortality of S. zeamais exposed to essential oil from C. sempervirens impregnated on filter paper
discs.

100
90
80
70
% mortality

60
0µl/cm2
50
40 0.19µl/cm2
30 0.39µl/cm2
20 0.78µl/cm2
10 1.56µl/cm2
0
0 1 2 3 4 5
Exposure time (days)

Fig. 2. Percentage mortality of S. zeamais exposed to essential oil from E. saligna impregnated on filter paper discs.

100
90
80
70
% mortality

60
50 0µl/cm2
40 0.19µl/cm2
30 0.39µl/cm2
20 0.78µl/cm2
10
1.56µl/cm2
0
0 1 2 3 4
Exposure time (days)

Fig. 3. Percentage mortality of T. confusum exposed to essential oil from C. sempervirens impregnated on filter paper
discs.

From the probit analyses, the calculated regression line equation of the third day data for S.
zeamais was Y=2.92 X+1.65 for Eucalyptus oil and Y=2.56 X+1.14 for Cupressus oil. Similarly
the third day data analysis for T. confusum gave Y=4.99 X-1.12 for Eucalyptus oil and
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A.L. Tapondjou et al. / Journal of Stored Products Research 41 (2005) 91–102 97

100
90
80
70

% mortality
60
50 0µl/cm2
40 0.19µl/cm2
30 0.39µl/cm2
20 0.78µl/cm2
10
1.56µl/cm2
0
0 1 2 3 4
Exposure time (days)

Fig. 4. Percentage mortality of T. confusum exposed to essential oil from E. saligna impregnated on filter paper discs.

Table 2
LD50 and LD95 calculated for mortality within 3 days of exposure of S. zeamais and T. confusum on filter paper-
impregnated essential oils and cymol
Pest species Phytochemical LD50 (ml/cm2) LD95 (ml/cm2)
S. zeamais
Eucalyptus oil 0.36 1.33
Cupressus oil 0.84 3.65
Cymol 1.35 3.94
T. confusum
Eucalyptus oil 0.48 1.20
Cupressus oil 0.74 2.42
Cymol 0.96 1.09

Y=3.21 X+0.32 for Cupressus oil. Comparison of LD50 values for the two oils against both insect
species showed that Eucalyptus oil was relatively more toxic (LD50=0.36 ml/cm2) than Cupressus
oil (LD50=0.84 ml/cm2) to S. zeamais. The same trend was observed in T. confusum with an LD50
of 0.48 ml/cm2 for Eucalyptus oil and 0.74 ml/cm2 for Cupressus oil (Table 2).
The lowest dosage of cymol (0.78 ml/cm2) induced no mortality of T. confusum within 5 days of
exposure while the highest dose of 1.30 ml/cm2 induced total mortality after one day (Fig. 5). The
effect was quite different with S. zeamais whereby 34% mortality of insects was registered after 5
days of exposure for the lowest dosage (0.78 ml/cm2) and 71% mortality with the highest dosage of
1.30 ml/cm2 (Fig. 6). The results of probit analysis showed that T. confusum was comparatively
more susceptible (LD50=0.96 ml/cm2) to the toxic effect of cymol than S. zeamais (LD50=1.35 ml/
cm2) (Table 2).

3.3. Contact toxicity of essential oils to S: zeamais; F1 progeny production and weight loss in maize
grains

Eucalyptus oil was more toxic to S. zeamais than Cupressus oil, total mortality of insects being
obtained at 100 ml/40 g grain within 1 day of exposure (Fig. 7). Cupressus oil, on the other hand
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100
90
80
70

% mortality
60
50
40 0µl/cm2
30 0.78µl/cm2
20
1.04µl/cm2
10
0 1.30µl/cm2
0 1 2 3 4 5
Exposure time (days)

Fig. 5. Percentage mortality of T. confusum exposed to cymol-impregnated-filter paper discs

80
70
60
% mortality

50
40
30 0µl/cm2
20 0.78µl/cm2
1.04µl/cm2
10
1.30µl/cm2
0
0 1 2 3 4 5
Exposure time (days)

Fig. 6. Percentage mortality of S. zeamais exposed to cymol-impregnated-filter paper discs.

100
90
80
70
% mortality

60
50
40 0µl/40g grain
30 50µl/40g grain
20 75µl/40g grain
10
100µl/40g grain
0
0 1 2 4
Exposure time (days)

Fig. 7. Percentage mortality of S. zeamais exposed to E. saligna oil coated on maize grain.

induced 80% mortality within the same exposure time (Fig. 8). Probit analyses confirmed that
Eucalyptus oil was more toxic (LD50=38.05 ml/40 g grain) to S. zeamais than Cupressus oil
(LD50=68.13 ml/40 g grain) when coated on maize grains.
All doses of oils caused significant reduction in progeny produced by the insects (Table 3). The
progeny production was completely suppressed on grains treated at the doses of 75 and 100 ml/40 g
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A.L. Tapondjou et al. / Journal of Stored Products Research 41 (2005) 91–102 99

100
90
80
70

% mortality
60
50
40 0µl/40g grain
30 50µl/40g grain
20 75µl/40g grain
10
100µl/40g grain
0
0 1 2 4
Exposure time (days)

Fig. 8. Percentage mortality of S. zeamais exposed to C. sempervirens oil coated on maize grain.

Table 3
F1 progeny production of S. zeamais and weight loss in grain treated with essential oils
Dose (ml/40 g grain) Mean number of % reduction in % grain weight loss
F1 adult progeny7SEM adult emergence
C. sempervirens
50 5473 27 3
75 5175 31 3
100 0 100 0

E. saligna
50 2473 68 6
75 0 100 0
100 0 100 0

Control 74714 — 20

grain. Moreover all the doses of the two oils reduced the grain weight loss compared to controls
(Table 3).

3.4. Repellency

Table 4 gives the average repellency values for each of the test oils and cymol on T. confusum
and S. zeamais. There was no significant variation in the repellent effects of the test oils and both
were highly repellent to the two insect species (PR>70%) compared to cymol that had a
significantly lower repellency effect (PRo60%).

4. Discussion

The toxic and repellent effects of phytochemicals on S. zeamais and T. confusum depend on
several factors among which are the chemical composition of the crude oil and insect susceptibility
(Casida, 1990).
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Table 4
Repellent effects of cymol and volatile oils from C. sempervirens and E. saligna on S. zeamais and T. confusum
% mean repellency Repellency class
S. zeamais
Eucalyptus oil 73715 IV
Cupressus oil 9874 V
Cymol 55711 III

T. confusum
Eucalyptus oil 9874 V
Cupressus oil 90710 V
Cymol 3278 II

Maize grains treated separately with each crude oil extract were highly toxic to S. zeamais
and both oil extracts or cymol-impregnated-filter paper discs were highly toxic to the two
insect species. This suggests that the toxicity of the crude oils was not due to ingestion of treated
grain.
Crude oil extracts from both plants exhibited greater repellent and/or toxic effects against the
test insects than did cymol, indicating that the crude oils contain other components that
increase their repellency and/or toxicity. The highly toxic and repellent effects of some of the
other main constituents of these oils such as 1,8-cineole, terpineol and a-pinene have been
demonstrated by other researchers. Obeng-Ofori et al. (1997) found 1,8-cineole to be highly
repellent and toxic to Sitophilus granarius L., S. zeamais, Tribolium confusum and Prostephanus
truncatus (Horn), and Ojimelukwe and Adler (1999) found a-pinene and terpineol to possess
potent repellent and toxic effects to Tribolium confusum. The toxic effects of the crude oil
extracts could also be attributed to an enhancing effect of some other minor constituents such as
limonene which was previously found to exhibit insecticidal activity against Rhyzopertha dominica
(F.) and Tribolium castaneum (Herbst) (Prates et al., 1998). Concerning the mode of action of
cymol and the crude oil extracts that are mainly constituted of mono-and sesqui-terpenoids, Ryan
and Byrne (1988) suggested that the toxic effect may be attributed to reversible competitive
inhibition of acetylcholinesterase by occupation of the hydrophobic site of the enzyme’s active
centre.
A good level of control of the test insects was achieved with cymol and the essential oils
extracted from C. sempervirens and E. saligna leaves. This demonstrates a scientific rationale for
the incorporation of the leaves of these plants into grain protection practices of communities in
the Western highlands of Cameroon. Additionally this research provides a scientific basis for
extracting and applying phytochemicals from C. sempervirens and E. saligna for stored-product
protection in the Western highlands of Cameroon. Moreover, provided with a proper formulation
and dosage, crude oils may be exploited for use against insect infestation at the small scale
farmer’s level since they may be more effective and less cumbersome than application of dried
foliage. The effects of these crude volatile oils are not particularly dangerous to consumers since
they are commonly used in many pharmaceutical preparations (Bauer et al., 1990) and they also
should easily evaporate during cooking of the foodstuff.
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Acknowledgements

This research project was supported by the German Academic Exchange program (DAAD) and
the Third World Academy of Science (TWAS). The Federal Biological Research Centre for
Agriculture and Forestry, Institute for Stored Product Protection, Berlin and all its staff is
thanked for providing laboratory facilities and equipment for this work. Dr C. Bauemann of the
Institute fur Getreide Verarbeitung GmbH, Postdam is gratefully acknowledged for helping in
chemical analyses of essential oils.

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