Malathion

Malathion is an organophosphate insecticide which

acts as an acetylcholinesterase inhibitor. In the Malathion
USSR, it was known as carbophos, in New Zealand
and Australia as maldison and in South Africa as
mercaptothion.

Contents
Pesticide use
Mechanism of action
Production method
Medical use
Risks
General
Carcinogenicity
Attention-deficit/hyperactivity disorder
Amphibians
See also
References
External links
Names

Pesticide use IUPAC name

Diethyl 2-
Malathion is a pesticide that is widely used in [(dimethoxyphosphorothioyl)sulfanyl]butanedioat
agriculture, residential landscaping, public e
recreation areas, and in public health pest control Other names
programs such as mosquito eradication.[5] In the US, 2-(Dimethoxyphosphinothioylthio) butanedioic
it is the most commonly used organophosphate acid diethyl ester
insecticide.[6] Malathion
A malathion mixture with corn syrup was used in Carbofos
the 1980s in Australia and California to combat the Maldison
Mediterranean fruit fly.[7] In Canada and the US, Mercaptothion
malathion was sprayed in many cities to combat Ortho malathion
west Nile virus. Malathion was used over the last Identifiers
couple of decades on a regular basis during summer
CAS Number 121-75-5 (http://www.commonc
months to kill mosquitoes, but homeowners were
allowed to exempt their properties if they chose. hemistry.org/ChemicalDetail.as
Today, Winnipeg is the only major city in Canada px?ref=121-75-5)
with an ongoing malathion adult-mosquito-control 3D model (JSmol) Interactive image (https://chem
program.[8][9]
 apps.stolaf.edu/jmol/jmol.php?
Mechanism of action
model=O%3DC%28OCC%29
C%28SP%28%3DS%29%28O
Malathion is an acetylcholinesterase inhibitor, a
diverse family of chemicals. Upon uptake into the C%29OC%29CC%28%3DO%
target organism, it binds irreversibly to several 29OCC)
random serine residues on the cholinesterase ChEBI CHEBI:6651 (https://www.ebi.a
enzyme. The resultant phosphoester group is
c.uk/chebi/searchId.do?chebiId
strongly bound to the cholinesterase, and
=6651)
irreversibly deactivates the enzyme which leads to
rapid build-up of acetylcholine at the synapse.[10] ChEMBL ChEMBL1200468 (https://www.
ebi.ac.uk/chembldb/index.php/
Production method compound/inspect/ChEMBL12
00468)
Malathion is produced by the addition of dimethyl ChemSpider 3864 (http://www.chemspider.c
dithiophosphoric acid to diethyl maleate or diethyl
om/Chemical-Structure.3864.ht
fumarate. The compound is chiral but is used as a
ml)
racemate.
DrugBank DB00772 (https://www.drugban
Medical use k.ca/drugs/DB00772)
ECHA InfoCard 100.004.089 (https://echa.euro
Malathion in low doses (0.5% preparations) is used pa.eu/substance-information/-/
as a treatment for: substanceinfo/100.004.089)

Head lice and body lice. Malathion is KEGG D00534 (https://www.kegg.jp/e

approved by the US Food and Drug ntry/D00534)
Administration for treatment of
PubChem CID 4004 (https://pubchem.ncbi.nl
pediculosis.[11][12] It is claimed to effectively
kill both the eggs and the adult lice, but in m.nih.gov/compound/4004)
fact has been shown in UK studies to be UNII U5N7SU872W (https://fdasis.nl
only 36% effective on head lice, and less so
m.nih.gov/srs/srsdirect.jsp?reg
on their eggs.[13] This low efficiency was
no=U5N7SU872W)
noted when malathion was applied to lice
found on schoolchildren in the Bristol area CompTox DTXSID4020791 (https://compt
in the UK, and it is assumed to be caused Dashboard (EPA)
ox.epa.gov/dashboard/DTXSID
by the lice having developed resistance
4020791)
against malathion.
Scabies[14] InChI
InChI=1S/C10H19O6PS2/c1-5-15-9(11)7-8(10(12)16-6-2)19-17(1
Preparations include Derbac-M, Prioderm, 8,13-3)14-4/h8H,5-7H2,1-4H3
[15] [16] Key: JXSJBGJIGXNWCI-UHFFFAOYSA-N
Quellada-M and Ovide.
InChI=1/C10H19O6PS2/c1-5-15-9(11)7-8(10(12)16-6-2)19-17(18,1
3-3)14-4/h8H,5-7H2,1-4H3

Risks Key: JXSJBGJIGXNWCI-UHFFFAOYAK

SMILES
O=C(OCC)C(SP(=S)(OC)OC)CC(=O)OCC
General Properties

Malathion is of low toxicity; however, absorption or Chemical formula C10H19O6PS2

ingestion into the human body readily results in its Molar mass 330.358021
metabolism to malaoxon, which is substantially
Appearance Clear colorless liquid
more toxic.[17] In studies of the effects of long-term
exposure to oral ingestion of malaoxon in rats, Density 1.23 g/cm3
malaoxon has been shown to be 61 times more toxic Melting point 2.9 °C (37.2 °F; 276.0 K)
than malathion,[17] and malaoxon is 1,000 times
more potent than malathion in terms of its Boiling point 156 to 157 °C (313 to 315 °F;
acetylcholinesterase inhibition.[18] Indoor spillage of 429 to 430 K) at 0.7 mmHg
malathion can thus be more poisonous than Solubility in water 145 mg/L at 20 °C[1]
expected, as malathion breaks down in a confined
Solubility Soluble in ethanol and
space into the more toxic malaoxon. It is cleared
acetone; very soluble in ethyl
from the body quickly, in three to five days.[19]
ether
According to the United States Environmental log P 2.36 (octanol/water)[2]
Protection Agency there is currently no reliable
Pharmacology
information on adverse health effects of chronic
exposure to malathion.[20] Acute exposure to ATC code P03AX03 (WHO (https://www.
extremely high levels of malathion will cause body- whocc.no/atc_ddd_index/?cod
wide symptoms whose intensity will be dependent e=P03AX03)) QP53AF12
on the severity of exposure. Symptoms include skin (WHO (https://www.whocc.no/a
and eye irritation, cramps, nausea, diarrhea, tcvet/atcvet_index/?code=QP5
excessive sweating, seizures and even death. Most 3AF12))
symptoms tend to resolve within several weeks.
Malathion present in untreated water is converted to Hazards
malaoxon during the chlorination phase of water Flash point 163 °C; 325 °F; 436 K (greater
treatment, so malathion should not be used in waters than)[3]
that may be used as a source for drinking water, or
Lethal dose or concentration (LD, LC):
any upstream waters.
LD50 (median 290 mg/kg (rat, oral)
In jurisdictions which spray malathion for pest dose) 190 mg/kg (mouse, oral)
control, it is often recommended to keep windows 570 mg/kg (guinea pig, oral)[4]
closed and air conditioners turned off while spraying
is taking place, in an attempt to minimize entry of LC50 (median 84.6 mg/m3 (rat, 4 hr)[4]
concentration)
malathion into the closed environment of residential
homes. LCLo (lowest 10 mg/m3 (cat, 4 hr)[4]
published)
In 1981, B. T. Collins,[21] director of the California NIOSH (US health exposure limits):
Conservation Corps, publicly swallowed a mouthful
PEL (Permissible) TWA 15 mg/m3 [skin][3]
of dilute malathion solution to demonstrate its safety
following an outbreak of Mediterranean fruit flies in REL TWA 10 mg/m3 [skin][3]
California. Malathion was sprayed over a (Recommended)
1,400 sq mi (3,600 km2) area to control the flies.[22] IDLH (Immediate 250 mg/m3[3]
danger)
In 1976, numerous malaria workers in Pakistan were Except where otherwise noted, data are given for
poisoned by isomalathion, a contaminant that may materials in their standard state (at 25 °C [77 °F],
be present in some preparations of malathion.[23] It 100 kPa).
is capable of inhibiting carboxyesterase enzymes in verify (what is ?)
those exposed to it. It was discovered that poor work
practices had resulted in excessive direct skin Infobox references
contact with isomalathion contained in the
malathion solutions. Implementation of good work practices, and the cessation of use of malathion
contaminated with isomalathion led to the cessation of poisoning cases.

Malathion is flammable. Patients using this agent should not be exposed to heat sources when it is applied,
such as blow dryers, cigarettes, or cooking flames.
Carcinogenicity

Malathion is classified by the IARC as probable carcinogen (group 2A). Malathion is classified by US EPA
as having "suggestive evidence of carcinogenicity".[24] This classification was based on the occurrence of
liver tumors at excessive doses in mice and female rats and the presence of rare oral and nasal tumors in rats
that occurred following exposure to very large doses. Researchers conducted a study involving participants
from six Canadian provinces and found that exposure to organophosphates as a group and malathion alone
was associated with non-Hodgkin's lymphoma. Malathion used as a fumigant was not associated with
increased cancer risk. Between 1993 and 1997, as part of the Agricultural Health Study, researchers
surveyed 19,717 pesticide applicators about their past pesticide exposures and health histories and no clear
association between malathion exposure and cancer was reported.[25]

Attention-deficit/hyperactivity disorder

A May 2010 study found that in a representative sample of US children, those with higher levels of
organophosphate pesticide metabolites in their urine were more likely to have attention-deficit/hyperactivity
disorder, but no causal relationship was established.[26] Each 10-fold increase in urinary concentration of
organophosphate metabolites was associated with a 55% to 72% increase in the odds of ADHD. The study
was the first investigation on children's neurodevelopment to be conducted in a group with no particular
pesticide exposure.[26][27]

Amphibians

Although current EPA regulations do not require amphibian testing, a 2008 study done by the University of
Pittsburgh found that "cocktails of contaminants", which are frequently found in nature, were lethal to
leopard frog tadpoles. They found that a combination of five widely used insecticides (carbaryl,
chlorpyrifos, diazinon, endosulfan, and malathion) in concentrations far below the limits set by the EPA
killed 99% of leopard frog tadpoles.[28]

See also
1989 California medfly attack
Pesticide toxicity to bees

References
1. Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium, 11th ed., British Crop
Protection Council, Surrey, England 1997, p. 755
2. Hansch, C., Leo, A., D. Hoekman. Exploring QSAR - Hydrophobic, Electronic, and Steric
Constants. Washington, DC: American Chemical Society., 1995., p. 80
3. NIOSH Pocket Guide to Chemical Hazards. "#0375" (https://www.cdc.gov/niosh/npg/npgd037
5.html). National Institute for Occupational Safety and Health (NIOSH).
4. "Malathion" (https://www.cdc.gov/niosh/idlh/121755.html). Immediately Dangerous to Life and
Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
5. Malathion for mosquito control (http://www.epa.gov/opp00001/health/mosquitoes/malathion4m
osquitoes.htm#malathion), US EPA
 6. Bonner MR, Coble J, Blair A, et al. (2007). "Malathion Exposure and the Incidence of Cancer
in the Agricultural Health Study". American Journal of Epidemiology. 166 (9): 1023–1034.
doi:10.1093/aje/kwm182 (https://doi.org/10.1093%2Faje%2Fkwm182). PMID 17720683 (http
s://pubmed.ncbi.nlm.nih.gov/17720683).
7. Edwards JW, Lee SG, Heath LM, Pisaniello DL (2007). "Worker exposure and a risk
assessment of malathion and fenthion used in the control of Mediterranean fruit fly in South
Australia". Environ. Res. 103 (1): 38–45. Bibcode:2007ER....103...38E (https://ui.adsabs.harva
rd.edu/abs/2007ER....103...38E). doi:10.1016/j.envres.2006.06.001 (https://doi.org/10.1016%2
Fj.envres.2006.06.001). PMID 16914134 (https://pubmed.ncbi.nlm.nih.gov/16914134).
8. Winnipeg, City of. "Insect Control - Public Works - City of Winnipeg" (https://winnipeg.ca/public
works/insectcontrol/default.stm). winnipeg.ca.
9. "Malathion winnipeg" (http://www.podolsky.ca/gary/Malathionwinnipeg.htm). www.podolsky.ca.
10. Colovic, Mirjana B.; Krstic, Danijela Z.; Lazarevic-Pasti, Tamara D.; Bondzic, Aleksandra M.;
Vasic, Vesna M. (2013). "Acetylcholinesterase Inhibitors: Pharmacology and Toxicology" (http
s://www.ncbi.nlm.nih.gov/pmc/articles/PMC3648782). Current Neuropharmacology. 11 (3):
315–335. doi:10.2174/1570159X11311030006 (https://doi.org/10.2174%2F1570159X1131103
0006). PMC 3648782 (https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3648782).
PMID 24179466 (https://pubmed.ncbi.nlm.nih.gov/24179466).
11. "Guidelines for the diagnosis and treatment of pediculosis capitis (head lice) in children and
adults 2008" (https://web.archive.org/web/20130226070624/http://www.guideline.gov/content.a
spx?id=12784). National Guideline Clearinghouse. Archived from the original (https://guideline.
gov/content.aspx?id=12784) on 2013-02-26. Retrieved 2013-01-22.
12. Amy J. McMichael; Maria K. Hordinsky (2008). Hair and Scalp Diseases: Medical, Surgical,
and Cosmetic Treatments (https://books.google.com/?id=W-dT_21KZOIC&pg=PA289).
Informa Health Care. pp. 289–. ISBN 978-1-57444-822-1. Retrieved 27 April 2010.
13. Downs AM, Stafford KA, Harvey I, Coles GC (1999). "Evidence for double resistance to
permethrin and malathion in head lice". Br. J. Dermatol. 141 (3): 508–11. doi:10.1046/j.1365-
2133.1999.03046.x (https://doi.org/10.1046%2Fj.1365-2133.1999.03046.x). PMID 10583056
(https://pubmed.ncbi.nlm.nih.gov/10583056).
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Oski's pediatrics: principles & practice (https://books.google.com/?id=VbjFQiz8aR0C&pg=RA1
-PA1383). Lippincott Williams & Wilkins. pp. 1–. ISBN 978-0-7817-3894-1. Retrieved 27 April
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ps://www.worldcat.org/search?fq=x0:jrnl&q=n2:0260-535X)
16. "AHFS Drug Information" (http://www.medicinescomplete.com/mc/ahfs/current/a384040.htm).
American Society of Health-System Pharmacists. 13 January 2011. Retrieved 17 January
2011.
17. Edwards D (2006). "Reregistration Eligibility Decision for Malathion" (http://www.epa.gov/pestic
ides/reregistration/REDs/malathion_red.pdf) (PDF). US Environmental Protection Agency -
Prevention, Pesticides and Toxic Substances EPA 738-R-06-030 Journal: 9.
18. Rodriguez, O. P.; Muth, G. W.; Berkman, C. E.; Kim, K.; Thompson, C. M. (February 1997).
"Inhibition of various cholinesterases with the enantiomers of malaoxon". Bulletin of
Environmental Contamination and Toxicology. 58 (2): 171–176. doi:10.1007/s001289900316
(https://doi.org/10.1007%2Fs001289900316). ISSN 0007-4861 (https://www.worldcat.org/issn/
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s.latimes.com/2010/may/16/science/la-sci-pesticides-20100517). Los Angeles Times.
20. "US Department of Health and Human Services: Agency for Toxic Substances and Disease
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g154.html). Retrieved 2008-04-02.
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workers". Lancet. 1 (8054): 31–4. doi:10.1016/S0140-6736(78)90375-6 (https://doi.org/10.101
6%2FS0140-6736%2878%2990375-6). PMID 74508 (https://pubmed.ncbi.nlm.nih.gov/74508).
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25. "Active Ingredient Fact Sheets" (http://npic.orst.edu/ingred/aifact.html). npic.orst.edu.
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2). Medscape Today. May 17, 2010. Retrieved Dec 11, 2012.
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ciencedaily.com/releases/2008/11/081111183041.htm). Science Daily. November 18, 2008.
Retrieved December 11, 2012.

External links
Malathion Technical Fact Sheet - National Pesticide Information Center (http://npic.orst.edu/fac
tsheets/malatech.pdf)
Malathion General Fact Sheet - National Pesticide Information Center (http://npic.orst.edu/fact
sheets/malagen.pdf)
Malathion Pesticide Information Profile - Extension Toxicology Network (http://extoxnet.orst.ed
u/pips/malathio.htm)
ATSDR ToxFAQs (https://web.archive.org/web/20130509193404/http://www.atsdr.cdc.gov/tfact
s154.html)
CDC - NIOSH Pocket Guide to Chemical Hazards (https://www.cdc.gov/niosh/npg/npgd0375.ht
ml)
Re-evaluation of Malathion (http://collection.nlc-bnc.ca/100/200/301/hcan-scan/pmra-arla/prop
osed_acceptability-e/pacr2003-10/pacr2003-10-e.pdf) by the Pest Management Regulatory
Agency of Canada
Malathion (http://sitem.herts.ac.uk/aeru/ppdb/en/Reports/421.htm) in the Pesticide Properties
DataBase (PPDB)

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