Environmental exposure and health risks of the insecticide monocrotophos - a review

J. Bio. & Env. Sci. 2014
111 | Kumar et al
REVIEW PAPER OPEN ACCESS
Environmental exposure and health risks of the insecticide
monocrotophos - a review
Vijay Kumar1*
, Niraj Upadhyay2
, Virender Kumar1
, Sukhmanpreet Kaur1
, Joginder
Singh3
, Simranjeet Singh3
, Shivika Datta4
1
Department of Chemistry, Lovely Professional University, Punjab, India
2
Department of Chemistry, Dr. Hari Singh Gour University, Sagar, Madhya Pradesh, India
3
Department of Biotechnology, Lovely Professional University, Punjab, India
4
Department of Zoology, Lovely Professional University, Punjab, India
Article published on July 08, 2014
Key words: Monocrotophos, toxicity, decomposition, isomers.
Abstract
Monocrotophos is a organophosphate based insecticide used for crop protection. Monocrotophos use has induced
heath issues and water pollution. From the ecotoxicology, human health and regulatory aspects, it is essential to
restrict the emissions and release of the highly acutely toxic chemical from the industrial processes and
agricultural applications. In this review, we present the toxicity and decomposition in media such as vegetables,
human tissues, animal tissues and rations, synthesis of the analytical procedures and materials used to determine
the monocrotophos and identification of cis and trans isomers of monocrotophos. Also the main physical
spectroscopic methods have been discussed in this review. The analytical techniques which are presented permit
to select the best analytical conditions to detect monocrotophos. These methods are widely applicable for
remaining organophosphate and other polar pesticides.
*Corresponding Author: Vijay Kumar  v.kumar8491@gmail.com
Journal of Biodiversity and Environmental Sciences (JBES)
ISSN: 2220-6663 (Print) 2222-3045 (Online)
Vol. 5, No. 1, p. 111-120, 2014
http://www.innspub.net

112 | Kumar et al
Introduction
Monocrotophos [(E)-dimethyl-1-methyl-3-
(methylamino)-3-oxo-1-propenyl phosphate (9Cl);
dimethyl phosphate ester with (E)-3-hydroxy- N-
methylcrotonamide (8 Cl)], trade names include
Nuvacron and Azodrin, is a broad-spectrum
organophosphate insecticide, acaricide, and
termiticide against gall midge, cutworms, corn
rootworms, cockroaches, leaf folder, and leaf hopper,
etc (Bhadbhade et al., 2002). Approximately 30,000
tons of MCP are used annually. As per data’s Asia is
the top user of MCP as; India (43%), South America
(26%), China (15%), and Southeast Asia (9%) account
for 90% of the use, internationally. In India Andhra
Pradesh and Punjab are the chief consumers of MCP
(WHO, 2009).
Studies, forced us to write about monocrotophos are
(1) regarding the unfortunately use of monocrotophos
in oil use for the mid-day meal (Bihar India) cooking
process for school student as result more than 30
student reported died
(http://www.hindustantimes.com, 2013), (2) a
hospital toxicity cases of monocrotophos, in India
where the proportion of identified pesticides
responsible for all deaths reported at MGM hospital,
Warangal, 1997-2001 approximately 54% death case
by the use of monocrotophos only has been occurred
and among the others column maximum were
organophosphates (WHO, 2009) (Fig. 1). Study
regarding monocrotophos become most important by
knowing the fact that, Asia is the top most consumer
of it and among Asian countries India (43%) is top
most consumer of monocrotophos and in India
Andhra Pradesh and Punjab are the chief consumers
of monocrotophos (Roberts et al., 2003; WHO,
2009).
Fig. 1.
One of the main agents for farmer suicides in India,
where the annual average reported cases was 17,366
in 2007, but thought to be up to 126,000 annually,
because it is the most commonly consumed
insecticide in India, with a case fatality rate of 35%
recorded (Roberts et al., 2003; WHO, 2009). In Sri
Lanka, the ban of monocrotophos and endosulfan has
reduced the number of deaths from suicide.
Monocrotophos has been linked to significant
occupational poisoning in Indonesia, Philippines,
Egypt, Brazil, and Central America (Roberts et al.,
2003; WHO, 2009). Monocrotophos (MCP) (Fig. 2)
was introduced in 1965 Ciba AG and Shell Chemical
Co. USA Company for widespread use as a foliar
insecticide for important crops such as rice, cereals,
cotton, tobacco, fruits, vegetable crops, pasture,
ornamental horticulture plants, and soil applications
to control termites (WHO, 2009). It exists in two
chemical or geometrical forms cis and trans, among
them cis is considered as active form (Ismail et al.,
2000). It has moderate to high toxicity, high water
solubility (1 kg/litre) and medium soil sorption
(organic carbon partitioning coefficient log Koc -0.20
l/kg) (Ismail et al., 2000; Tomlin C, 1995; WHO,
2009). The logarithm of the octanol–water
partitioning coefficients (log Kow) for monocrotophos
is -0.20 (Ismail et al., 2000; Tomlin C, 1995).
Fig. 2.
Fig. 1. Pie deaths reported at MGM hospital (India),
Warangal, 1997-2001 by the application of
monocrotophos.
O
P
O
O
O O
HN
Fig. 2. Structure of Monocrotophos.

113 | Kumar et al
Toxicity of Monocrotophos
Monocrotophos is a direct acting cholinesterase
inhibitor capable of penetration through the skin,
LD50, is 17-18 mg/kg for male rats and 20 mg/kg for
female rats. The LD50 for dermal exposure is 126
mg/kg for male rats, 112 mg/kg for female rats, and
354 mg/kg for rabbits. Monocrotophos is an
extremely toxic to aquatic invertebrates, birds and
mammals. It is toxic to most organisms and in
particular to birds (Swamy et al., 1992). The most
likely route of exposure to monocrotophos for the
public is via residues in food. The prolonged or
continued use of monocrotophos in plant protection
may lead to significant dermal exposure with an
impact on cholinesterase, genotoxicity and
cardiotoxicity activities (Bhunya SP and Jena GB.
1993; Schulze-Rosario C. and Loosli R. 1994; Swamy
et al., 1992). The toxicologically relevant mode of
action is the inhibition of acetylcholinesterase
(AChE) activities (Rao JV et al., 1992; Swamy et al.,
1992). The basic mechanism of AChE inhibition with
monocrotophos is analogous to the reaction of
enzyme with ACh, excluding for the reaction in which
the leaving group of the monocrotophos is lost, so the
enzyme becomes phosphorylated in-stead of
acetylated. Phosphorylation is a two-step addition-
elimination reaction in which the addition step is
rate-determining, while the elimination process is
faster. It should be noted that phosphorylation occurs
via a trigonal bipyramidal intermediate, whereas in
the case of acetylation is anticipated through a
tetrahedral intermediate. The irreversibly inhibited
phosphorylated enzyme can no longer hydrolyze
acetylcholine. This leads to an accumulation of
acetylcholine in cholinergic receptors and consequent
continuous stimulation of the nerve fiber.
Phosphorylated AChE having the stable bonding and
forces than acetylated one, but it can undergo a
possible secondary process. Among these first one is
the reactivation-hydrolysis of phosphorylated
enzyme. But the rate of hydrolysis is much slower
than in the case of an acetylated enzyme. Another
mechanism is the breaking of the PO-C bond the
inhibited enzyme known as “aging” (Kumar et al.,
2013). Monocrotophos is neurotoxic in nature and
caused a significant inhibition of the brain
acetylcholinesterase activity. There are age-related
differences in the inhibition of brain, but not
necessarily red blood cell and AChE. The sensitivity of
the tissue AChE was in the order gill>brain>muscle
(Moser, 2011; Rao et al., 2005).
Hyperglycemic and stressogenic
effects of monocrotophos have been observed,
hyperglycemia and hyperlactacidemia induced by
monocrotophos were abolished by pretreatment with
atropine (Joshi and Rajini, 2012). Higher
concentrations of monocrotophos caused acute
toxicity, which marked increase in mobility of cells
exhibiting rocking movements within two mins of
exposure but were decreased after 30 mins and
cytotoxic effects of monocrotophos revealed non-
repair of necrosis (Amanchi and Hussain, 2010).
Monocrotophos is genotoxic on meretrix ovum and
also induces a pollution stress related retardation of
somatic growth of this mussel (Revankar and
Shyama, 2009). Genotoxic mechanism in fish taken
placed by DNA damage and measured in the gill,
kidney and lymphocytes as the percentage of DNA in
comet tails of fish exposed to different sublethal and
nonlethal concentrations of monocrotophos (Jamil et
al., 2004).
Monocrotophos insecticide during sexual
development causes the
feminization/demasculinization of the reproductive
traits. Reproductive toxicity caused by
organophosphates (monocrotophos) at cellular and
molecular level in the ovaries of rat. Reproductive
toxicity of monocrotophos also has been observed in
bobwhite quail (Tian et al., 2012).
Monocrotophos has histopathological effects in liver,
kidney and muscles of normal, protein malnourished
and diabetic as well as both protein-malnourished,
diabetic albino rats and fish. Histopathological effects
of monocrotophos on the gill, kidney and intestine
tissues of the Cirrhinus mrigala were determined by

114 | Kumar et al
light microscopy (Srinivasulu et al., 2012;
Velmurugan et al., 2007).
Persistent and Contamination by Monocrotophos
Excessive use of monocrotophos has contaminated
several ecosystems. It has been suggested the ability
of monocrotophos, and other organophosphorus
pesticides to accumulate in living tissues may create a
potential risk to humans and other organisms (WHO,
2009). Combinations with other chemicals and higher
concentrations of monocrotophos have been
considered innocuous or inhibitory to the
phosphatase activity (Velmurugan et al., 2007). On
soils-black vertisol soil and red alfinsol soil under
laboratory conditions, interaction responses the
persistent of monocrotophos even for 30 days.
Monocrotophos have adverse effects on nontarget soil
microorganisms and their activities. It was expected
to undergo E/Z isomerization and cleavage of the P-O
vinyl linkage (Gundi et al., 2007; Vig et al., 2008).
The fate of monocrotophos in the aqueous and soil
environment was examined. Hydrolysis rates for
monocrotophos are pH-dependent and follow first-
order kinetics. The half-lives of monocrotophos in pH
3 and 9 buffer solution at 25oC are 131 and 26 days,
respectively. Its half-life is less than 7 days in soil
exposed to natural sunlight (Lee et al.,1990; Vig et al.,
2008).
Decomposition of Monocrotophos
The main mechanism of biotransformation of
monocrotophos was hydrolysis of the P-O vinyl
linkage, to give dimethyl phosphate and N-
methylacetoacetamide as major metabolites. The
mechanisms involved in the absorption, distribution,
metabolism, and elimination of monocrotophos seem
to be largely species independent. In the initial
biotransformation, three different metabolic reactions
occur: hydroxylation of the N-methyl group,
demethylation of the N-methyl group, and hydrolysis
of the phosphate-vinyl linkage (Gundi et al., 2006;
Lee et al.,1990; Vig et al., 2006). The degradation of
monocrotophos in black vertisol and red alfinsol soils
was rapid accounting for 96-98% of the applied
quantity and followed the first-order kinetics with
rate constants of 0.0753 and 0.0606 day-1 and half-
lives (t1/2) of 9.2 and 11.4 days, respectively.
Degradation of monocrotophos in soils proceeded by
hydrolysis with formation of N-
methylacetoacetamide. Monocrotophos show the
dissipation and leaching behavior in soil and water,
14C-monocrotophos dissipated faster, up to 45% in
first 90 days in columns treated with only
monocrotophos compared to 25% in columns that
received monocrotophos along with other
insecticides. After 180 days of treatment, 46% radio
labeled residues were observed, which reduced up to
39.6% after 365 days (Gundi et al., 2006; Lee et
al.,1990; Vig et al., 2006). Leaching of 14C-
monocrotophos to 15-30 cm soil layer was observed in
both the experimental setups. In the 15-30 cm soil
layer of both soil columns, up to 0.19 mg 14C-
monocrotophos kg-1d wt. soil was detected after 270
days (Gundi et al., 2006; Lee et al.,1990; Vig et al.,
2006). Study reveal about the persistence of
monocrotophos in soils at different temperatures and
decay in the microbial activities in the presence of less
organic substances in soils. Monocrotophos is
unlikely to undergo photochemical reactions on soil
due to lack of chromophores in their molecules
(Gundi et al., 2006; Lee et al.,1990; Vig et al., 2006).
Analytical Procedures to Determine the
Monocrotophos
In past there have been different analytical
procedures and materials used to determine the
monocrotophos including other pesticides in media
such as soils, vegetables, human tissues, animal
tissues and rations (Hu et al., 2013; Kumar et al.,
2013; Prasad et al., 2011; Velmurugan et al., 2007).
But there is variability among the analytical
techniques which are presented permit to select the
best analytical conditions to detect monocrotophos.
On the basis of facilities of these techniques we
divided this section into two main parts i.e best
analytical techniques and procedure developed or
used to detect monocrotophos in its active form and
secondly in its fragments or metabolites detections.

115 | Kumar et al
Active form Determination Techniques
There are two best way to determine active form of
monocrotophos, firstly by using the analytical
methods and secondly by enzymatic approach. In first
one, monocrotophos can be determined by the
general procedure using the flame photometric
detector. Specific methods for monocrotophos using
this detector have been developed and allow analyses
of crops down to a limit of determination of 0.01ppm
(Hu et al., 2013). The following procedure has proved
satisfactory in analyzing crops: samples are extracted
by maceration with chloroform; low water content
crops are first dampened with water. The
monocrotophos-containing extract is analyzed using
the flame photometric detector. Using this procedure,
mean recoveries are 75 - 120% from crops at the 0.05
- 0.20 ppm level (Hu et al., 2013). The thermionic
detector has also been employed in the analyses of
crops for residues of monocrotophos. Mean
recoveries with this method are 80 - 120% for crops,
with a limit of determination of 0.03 - 0.05 ppm. The
study made use of the gas liquid chromatography for
the analysis of monocrotophos in extracts. The result
of the study shows that there is no degradation of
monocrotophos occurred in the dark while 72.8% of
the applied monocrotophos could be recovered when
exposure to sunlight for eight hours is done. Cold
drinks samples were filtered, degassed (if
carbonated), and analyzed using liquid
chromatography with tandem mass spectrometry, in
chromatogram monocrotophos and phorate were
observed at 101(25.7%) and 86.6 (20.7%) (Miller and
Milne, 2008). A method combining hydrophilic
interaction liquid chromatography with tandem mass
spectrometry was developed for the determination of
polar organophosphorus pesticides, method was
validated at 0.05, 0.5, and 5µg/L levels in water
samples, and the recoveries of polar OPPs were
between 76.4 and 98.6%. The limits of detection were
between 0.13 and 1.0 pg on-column, and the limits of
quantification were between 0.43 and 3.4 pg on-
column. The method can be applied to the
determination of trace amounts of organophosphate
pesticides in environmental water samples (Hayama
et al., 2008).
Enzymatic Methods
In enzymatic inhibition specific enzymatic methods
for the detection and determination of
monocrotophos in crops, vegetables and milk have
been developed. The samples for analysis are
extracted with chloroform, followed by a solvent
exchange to hexane and concentration of the extract.
Column chromatography using a gradient column
elution technique with hexane/dichloromethane
removes co-extractives. The separated
monocrotophos is transferred to water and
determined by enzyme inhibition spectrophotometric
methods. Using this procedure, the limit of
determination of monocrotophos is about 0.10 ppm
in crops and 0.01 ppm in milk. Recoveries are in the
range of 70 - 125% (Rao et al., 2002; Wu et al., 2011).
The other method the inhibition of monocrotophos
was proportional to its concentration ranging from
0.001 to 1 µg/ml, 2 to15 µg/ml with the correlation
coefficients of 0.9930 to 0.9985 respectively. The
detection limit was 0.6 nano g/ml at a 10% inhibition
(Rao et al., 2002; Wu et al., 2011). Methods for
analyses of monocrotophos breakdown products, the
analytical data for the N-methylol and for the un-
substituted amide reported in this summary were
developed using the method described for
monocrotophos. The conjugate of the N-methylol was
determined using the method, which depends on
converting the conjugate to the sec-butyl thio-ether of
the methylol and subsequent determination by T.L.C.
with detection limit lower than 0.2 mg and enzyme
inhibition (Janghel et al., 2007).
Isomeric Identification of Monocrotophos
As earlier mentioned monocrotophos exists in two
chemical or geometrical forms cis and trans, among
them cis is considered as active form (Ismail and Rao,
2000). A simple reversed-phase LC method has been
developed for the determination of cis and trans
isomers of MCP and its process related impurities
using a C18 bonded silica with water–acetonitrile

116 | Kumar et al
(87:13, v/v) as eluent and UV detection at 218 nm at
an ambient temperature has been described (Ismail
and Rao, 2000). In this method samples (100 mg)
were dissolved in small volumes of acetonitrile and
diluted with eluent (25 ml) and diluted to 10 ml and a
20-ml volume, injected and analyzed under the above
conditions. Analyses were carried out under isocratic
conditions at a flow-rate of 1.0 ml/min and a chart
speed of 5 mm/min at 278oC. All the chromatograms
were recorded at 218 nm. Excellent linearities
between the amounts taken and found by LC were
observed with regression coefficients greater than
0.9950. The contents of cis and trans-MCP were
found to decrease from day 0 to 30 from 72.5 to
71.760.4% RSD and 6.9 to 3.961.58% RSD,
respectively. These results clearly indicate that the
rates of decomposition of cis- and trans-MCP are
different. On decomposition both compounds yielded
a product which was identified as 4-hydroxy N-
methylcrotonamide by mass spectrometry.
Spectroscopic Methods
Ultraviolet-Visible Spectroscopy
A highly sensitive spectrophotometric method is
developed for the determination of parts per million
levels of widely used organophosphorus pesticide
MCP. The method is based on alkaline hydrolysis of
MCP to N-methylacetoacetamide followed by
coupling with diazotized 2, 4- dinitrophenyl
hydrazene in alkaline medium. The absorption
maxima of the yellow coloured compound formed is
measured at 490 nm (Sharma and Rajput 2012). A
simple reversed-phase column liquid
chromatographic method for the determination of cis
and trans isomers of MCP (MCP) using a C column,
aqueous acetonitrile as eluent and UV detection at
218 nm was developed. The method was used for
quality assurance and to study the relative stabilities
of cis and trans isomers in technical products of MCP
(Ismail and Rao, 2000).
Nuclear Magnetic Resonance Spectroscopy
A Molecular imprinting method based on noncovalent
interaction was used for the synthesis of a MCP-
specific polymer. The selective binding characteristics
of the template polymer were evaluated by 1H NMR
and ultraviolet spectrometry (Zhu et al., 2005). The
polymer obtained was found to interact specifically
with MCP by cooperative hydrogen bonding. The
infrared spectrometry of the polymer further
indicated that there were some functional groups in
the molecularly imprinted polymer which could
interact on the template. Because of polymeric nature
the life span raised 15 time more as copared to MCP
and the total number of binding sites of the polymer
were 4.046 µmg-1 (Zhu et al., 2005).
Sensor Based Detection
A simple, low cost, viable and sensitive enzymatic
method was developed, based on the inhibition of
enzyme, succinate dehydrogenase. The developed
enzymatic method was successfully applied for
detection, separation and identification of MCP from
environmental samples (Uma and Prameela, 2011).
To detect the MCP a sensitive amperometric
acetylcholinesterase (AChE) biosensor was fabricated
based on mesocellular silica foam (MSF), which
functioned as both an enzyme immobilization matrix
and a solid phase extraction (SPE) material for the
preconcentration of target molecules. A sensitive, fast
and stable amperometric sensor for quantitative
determination of organophosphorous insecticide was
developed using MCP as a model compound,
Developing the acetylcholinesterase (AChE) on silica
sol-gel film assembling gold nanoparticles the
conditions for detection of the insecticide were
optimized. The inhibition of MCP was proportional to
its concentration ranging from 0.001 to 1 microg/ml
and 2 to 15 µg/ml, with the correlation coefficients of
0.9930 and 0.9985, respectively. The detection limit
was 0.6 ng/ml at a 10% inhibition (Du et al., 2007;
Uma and Prameela, 2011).
Thin Layer Chromatography
TLC based method of separation of MCP from
dichlrovos was developed, phenolic compounds and
hydrolysed product of carbamate insecticides may
interfere and differentiate from MCP and dichlrovos

117 | Kumar et al
by Rf values. The lower limit of detection is 0.2 mg for
MCP and 0.1 mg for dichlorovos. The absorption
maxima of the reddish-violet and red colour by
diazotized with p-amino acetophenone formed by
MCP and dichlrovos, are measured at 560 nm and
540 nm respectively (Patil and Shingare, 1994;
Janghel et al., 2007).
Mass Spectroscopy
The study made use of the gas liquid chromatography
(GLC) for the analysis of MCP in extracts. The result
of the study shows that there is no degradation of
MCP occurred in the dark while 72.8% of the applied
MCP could be recovered when exposure to sunlight
for eight hours is done.49 Cold drinks samples were
filtered, degassed (if carbonated), and analyzed using
liquid chromatography with tandem mass
spectrometry, in chromatogram MCP and phorate
were observed at 101(25.7%) and 86.6 (20.7%)
(Hayama et al., 2008; Miller and Milne, 2008; Paske
et al., 2007; Rao et al., 2002). A method combining
hydrophilic interaction liquid chromatography with
tandem mass spectrometry was developed for the
determination of polar organophosphorus pesticides,
method was validated at 0.05, 0.5, and 5 µg/L levels
in water samples, and the recoveries of polar OPPs
were between 76.4 and 98.6%. The limits of detection
were between 0.13 and 1.0 pg on-column, and the
limits of quantification were between 0.43 and 3.4 pg
on-column (Hayama et al., 2008; Miller and Milne,
2008; Paske et al., 2007; Rao et al., 2002). The
method can be applied to the determination of trace
amounts of organophosphate pesticides in
environmental water samples. A simple and rapid GC-
MS method for separation, identification and
quantitative determination of combustion products of
organophosphorus and chlorine pesticides viz; MCP,
chloropyriphos, butachlor and benzenehexachloride
has been developed (Hayama et al., 2008; Miller and
Milne, 2008; Paske et al., 2007; Rao et al., 2002).
Summary of Methods including other Pesticides
Determination of sorption of hydrophilic, weakly
sorbing organic compounds in soil by conventional
batch methods using a slurried suspension is often
prone to considerable errors because small changes in
the solution concentration on equilibration must be
accurately determined. The unsaturated transient
flow method, which enables determination of
sorption at sufficiently small solution to soil ratios
was employed to check the sorption of pesticides and
compared with traditional method. The sorption
coefficient (Kd = 0.10 L kg-1) obtained for MCP was
slightly lower than that by batch method (Kd =0.19 L
kg-1) (Ahmad et al., 2005).
Till date most efficient method to detect the MCP
exclusively or in combination with other pesticides is
the gas chromatographic/mass spectrometric
method. Phorate’s residues have been qualitatively
confirmed at the 1 ppb level in fortified water samples
from a variety of sources. Apparent residues in
control water were less than 0.1 ppb (Singh et al.,
2009). Residues of MCP among the other pesticides
have been observed in apple, cucumber, green
vegetables (Mansour et al., 2009; Singh et al., 2009),
honey bees from the sunflowers (44%), citrus groves
(10%) and cotton field (35%), milk and potato
(Mansour et al., 2009; Pagliuca et al., 2006; Singh et
al., 2009). There are number of detection available
among them High-performance liquid
chromatography (HPLC), Gas Chromatography (GC)
and Thin layer chromatography (TLC) are considered
as major methods.
Conclusion
We conclude that monocrotophos is insecticide of
Asian countries especially India and having high
toxicity level for living beings especially to birds.
Monocrotophos cause the histopathological,
genotoxic, acute, hyperglycemic and stressogenic
effects and significant dermal exposure with an
impact on cholinesterase, genotoxicity and
cardiotoxicity activities.
The most common technique used in the
determination of the monocrotophos and its
metabolites is flame photometric detector followed by
liquid chromatography with tandem mass

118 | Kumar et al
spectrometry and gas chromatography with electron
capture detector. In most cases, this technique is
coupled with mass spectrometry.
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