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Malathion
Malathion
is an organophosphate insecticide which acts as an acetylcholinesterase inhibitor. In the USSR, it was known as carbophos, in New Zealand
New Zealand
and Australia
Australia
as maldison and in South Africa as mercaptothion.[5]

Contents

1 Pesticide
Pesticide
use 2 Mechanism of action, production method 3 Medical use 4 Risks

4.1 General 4.2 Attention-deficit/hyperactivity disorder 4.3 Carcinogenicity 4.4 Amphibians

5 See also 6 References 7 External links

Pesticide
Pesticide
use[edit] Malathion
Malathion
is a pesticide that is widely used in agriculture, residential landscaping, public recreation areas, and in public health pest control programs such as mosquito eradication.[6] In the US, it is the most commonly used organophosphate insecticide.[7] A Malathion
Malathion
mixture with corn syrup was used in the 1980s in Australia and California to combat the Mediterranean fruit fly.[8] In Canada and the US, malathion was[when?] sprayed in many cities to combat west Nile virus. Malathion
Malathion
was used over the last couple of decades[when?] on a regular basis during summer months to kill mosquitoes, but homeowners were allowed to exempt their properties if they chose[citation needed]. Today, Winnipeg
Winnipeg
is the only major city in Canada with an ongoing malathion adult-mosquito-control program.[9][10] Mechanism of action, production method[edit] Malathion
Malathion
is an acetylcholinesterase inhibitor, a diverse family of chemicals that includes sarin and carbaryl. Upon uptake into the target organism, it binds irreversibly to several, random serine residues on the cholinesterase enzyme, with a peroxide as the leaving group. The resultant phosphoester group is strongly bound to the cholinesterase, and irreversibly deactivates the enzyme which leads to rapid build-up of acetylcholine at the synapse[11]. It is produced by the addition of dimethyl dithiophosphoric acid to diethyl maleate. The compound is chiral but is used as a racemate. Medical use[edit] Malathion
Malathion
in low doses (0.5% preparations) is used as a treatment for:

Head lice
Head lice
and body lice. Malathion
Malathion
is approved by the US Food and Drug Administration for treatment of pediculosis.[12][13] It is claimed to effectively kill both the eggs and the adult lice, but in fact has been shown in UK studies to be only 36% effective on head lice, and less so on their eggs.[14] This low efficiency was found when malathion was applied to lice found on schoolchildren in the Bristol area in the UK and it is assumed[by whom?] to be caused by the lice having developed resistance against malathion. Scabies[15]

Preparations include Derbac-M, Prioderm, Quellada-M[16] and Ovide.[17] Risks[edit] General[edit] Malathion
Malathion
is of low toxicity; however, absorption or ingestion into the human body readily results in its metabolism to malaoxon, which is substantially more toxic.[18] In studies of the effects of long-term exposure to oral ingestion of malaoxon in rats, malaoxon has been shown to be 61 times more toxic than malathion.[18] It is cleared from the body quickly, in three to five days.[19] According to the United States Environmental Protection Agency there is currently no reliable information on adverse health effects of chronic exposure to malathion.[20] Acute exposure to extremely high levels of malathion will cause body-wide symptoms whose intensity will be dependent on the severity of exposure. Symptoms include skin and eye irritation, cramps, nausea, diarrhea, excessive sweating, seizures and even death. Most symptoms tend to resolve within several weeks. Malathion
Malathion
present in untreated water is converted to malaoxon during the chlorination phase of water treatment, so malathion should not be used in waters that may be used as a source for drinking water, or any upstream waters. In jurisdictions which spray malathion for pest control, it is often recommended to keep windows closed and air conditioners turned off while spraying is taking place, in an attempt to minimize entry of malathion into the closed environment of residential homes. In 1981, B. T. Collins,[21] director of the California Conservation Corps, publicly swallowed a mouthful of dilute malathion solution and survived. This was an attempt to demonstrate malathion's safety following an outbreak of Mediterranean fruit flies in California. Malathion
Malathion
was sprayed over a 1,400 sq mi (3,600 km2) area to control the flies.[22] In 1976, numerous malaria workers in Pakistan
Pakistan
were poisoned by isomalathion, a contaminant that may be present in some preparations of malathion.[23] It is capable of inhibiting carboxyesterase enzymes in those exposed to it. It was discovered that poor work practices had resulted in excessive direct skin 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
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. Attention-deficit/hyperactivity disorder[edit] 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.[24] 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.[24][25] Carcinogenicity[edit] Malathion
Malathion
is classified by the IARC as probable carcinogen (group 2A). Malathion
Malathion
is classified by US EPA as having "suggestive evidence of carcinogenicity".[26] 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
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.[27] Amphibians[edit] 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[edit]

1989 California medfly attack Pesticide
Pesticide
toxicity to bees

References[edit]

^ Tomlin, C.D.S. (ed.). The Pesticide
Pesticide
Manual - World Compendium, 11th ed., British Crop Protection Council, Surrey, England 1997, p. 755 ^ Hansch, C., Leo, A., D. Hoekman. Exploring QSAR - Hydrophobic, Electronic, and Steric Constants. Washington, DC: American Chemical Society., 1995., p. 80 ^ a b c d "NIOSH Pocket Guide to Chemical Hazards #0375". National Institute for Occupational Safety and Health (NIOSH).  ^ a b c "Malathion". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).  ^ "alanwood.net". Retrieved 2007-09-16.  ^ Malathion
Malathion
for mosquito control, US EPA ^ Bonner MR, Coble J, Blair A, et al. (2007). " Malathion
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. PMID 17720683.  ^ 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
Mediterranean fruit fly
in South Australia". Environ. Res. 103 (1): 38–45. doi:10.1016/j.envres.2006.06.001. PMID 16914134.  ^ Winnipeg.ca-UD: Public Works: Insect Control Branch ^ Malathion
Malathion
winnipeg ^ Colovic, MB; Krstic, Danijela Z.; Lazarevic-Pasti, Tamara D.; Bondzic, Aleksandra M.; Vasic, Vesna M. (2013). "Acetylcholinesterase Inhibitors: Pharmacology and Toxicology". Current Neuropharmacology. 11 (3): 315–335. doi:10.2174/1570159X11311030006. PMC 3648782 Freely accessible. PMID 24179466. ^ National Guideline Clearinghouse Guidelines for the diagnosis and treatment of pediculosis capitis (head lice) in children and adults 2008 ^ Amy J. McMichael; Maria K. Hordinsky (2008). Hair and Scalp Diseases: Medical, Surgical, and Cosmetic Treatments. Informa Health Care. pp. 289–. ISBN 978-1-57444-822-1. Retrieved 27 April 2010.  ^ 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. PMID 10583056.  ^ Julia A. McMillan; Ralph D. Feigin; Catherine DeAngelis; M. Douglas Jones (1 April 2006). Oski's pediatrics: principles & practice. Lippincott Williams & Wilkins. pp. 1–. ISBN 978-0-7817-3894-1. Retrieved 27 April 2010.  ^ British National Formulary 54th Ed. Sept 2007. ISBN 978-0-85369-736-7. ISSN 0260-535X ^ "AHFS Drug Information". American Society of Health-System Pharmacists. 13 January 2011. Retrieved 17 January 2011.  ^ a b Edwards D (2006). "Reregistration Eligibility Decision for Malathion" (PDF). US Environmental Protection Agency - Prevention, Pesticides and Toxic Substances EPA 738-R-06-030 journal: 9.  ^ Maugh II, Thomas H. (16 May 2010). "Study links pesticide to ADHD in children". Los Angeles Times.  ^ "US Department of Health and Human Services: Agency for Toxic Substances and Disease Registry - Medical Management Guidelines for Malathion". Retrieved 2008-04-02.  ^ "California Death Index, 1940-1997 [Database Online]". Provo, Utah: The Generations Network. 2000. Retrieved 2009-12-14.  ^ Bonfante, Jordan (1990-01-08). "Medfly Madness". TIME. Retrieved May 21, 2009.  ^ Baker EL, Warren M, Zack M, et al. (1978). "Epidemic malathion poisoning in Pakistan
Pakistan
malaria workers". Lancet. 1 (8054): 31–4. doi:10.1016/S0140-6736(78)90375-6. PMID 74508.  ^ a b Bouchard, M. F.; Bellinger, D. C.; Wright, R. O.; Weisskopf, M. G. (2010). "Attention-Deficit/Hyperactivity Disorder and Urinary Metabolites of Organophosphate
Organophosphate
Pesticides". Pediatrics. 125 (6): e1270–7. doi:10.1542/peds.2009-3058. PMC 3706632 . PMID 20478945.  ^ " Organophosphate
Organophosphate
Pesticides Linked to ADHD". Medscape Today. May 17, 2010. Retrieved Dec 11, 2012.  ^ Reregistration Eligibility Decision for Malathion
Malathion
(Revised), US EPA, May 2009 ^ Malathion
Malathion
Technical Fact Sheet ^ "Low Concentrations Of Pesticides Can Become Toxic Mixture For Amphibians". Science Daily. November 18, 2008. Retrieved December 11, 2012. 

External links[edit]

Malathion
Malathion
Technical Fact Sheet - National Pesticide
Pesticide
Information Center Malathion
Malathion
General Fact Sheet - National Pesticide
Pesticide
Information Center Malathion
Malathion
Pesticide
Pesticide
Information Profile - Extension Toxicology Network ATSDR ToxFAQs CDC - NIOSH Pocket Guide to Chemical Hazards Re-evaluation of Malathion
Malathion
by the Pest Management Regulatory Agency of Canada Malathion
Malathion
in the Pesticide
Pesticide
Properties DataBase (PPDB)

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Organochlorides

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Organophosphorus

Acephate Azamethiphos Azinphos-methyl Bensulide Chlorethoxyfos Chlorfenvinphos Chlorpyrifos Chlorpyrifos-methyl Coumaphos Demeton-S-methyl Diazinon Dicrotophos Diisopropyl fluorophosphate Dimefox Dimethoate Dioxathion Disulfoton Ethion Ethoprop Fenamiphos Fenitrothion Fenthion Fosthiazate Isoxathion Malathion Methamidophos Methidathion Mevinphos Monocrotophos Naled Omethoate Oxydemeton-methyl Parathion Parathion-methyl Phenthoate Phorate Phosalone Phosmet Phoxim Pirimiphos-methyl Quinalphos Temefos Tebupirimfos Terbufos Tetrachlorvinphos Tribufos Trichlorfon

Pyrethroids

Acrinathrin Allethrins Bifenthrin Bioallethrin Cyfluthrin Cyhalothrin Cypermethrin Cyphenothrin Deltamethrin Empenthrin Esfenvalerate Etofenprox Fenpropathrin Fenvalerate Flumethrin Imiprothrin Metofluthrin Permethrin Phenothrin Prallethrin Pyrethrin
Pyrethrin
(I, II; chrysanthemic acid) Pyrethrum Resmethrin Silafluofen Tefluthrin Tetramethrin Tralomethrin Transfluthrin

Ryanoids

Chlorantraniliprole Cyantraniliprole Flubendiamide Ryanodine Ryanodol

Other chemicals

Afoxolaner Amitraz Azadirachtin Buprofezin Chlordimeform Chlorfenapyr Cyromazine Fenazaquin Fenoxycarb Fipronil Fluralaner Hydramethylnon Indoxacarb Limonene Lotilaner Pyridaben Pyriprole Ryanodine Sarolaner Sesamex Spinosad Sulfluramid Tebufenozide Tebufenpyrad Veracevine Xanthone Metaflumizone

Metabolites

Oxon Malaoxon Paraoxon TCPy

Biopesticides

Bacillus thuringiensis Baculovirus Beauveria bassiana Beauveria brongniartii Metarhizium acridum Metarhizium anisopliae Nomuraea rileyi Lecanicillium lecanii Paecilomyces fumosoroseus Paenibacillus popilliae Purpureocillium
Purpureocillium
lilacinum

v t e

Acetylcholine
Acetylcholine
metabolism and transport modulators

Enzyme (modulators)

ChAT

Inhibitors: 1-(-Benzoylethyl)pyridinium 2-(α-Naphthoyl)ethyltrimethylammonium 3-Chloro-4-stillbazole 4-(1-Naphthylvinyl)pyridine Acetylseco hemicholinium-3 Acryloylcholine AF64A B115 BETA CM-54,903 N,N-Dimethylaminoethylacrylate N,N-Dimethylaminoethylchloroacetate

AChE

Inhibitors: Reversible: Carbamates: Aldicarb Aminocarb Bendiocarb Bufencarb Carbaryl Carbendazim Carbetamide Carbofuran Carbosulfan Chlorbufam Chloropropham Dimetilan Ethienocarb Ethiofencarb Fenobucarb Formetanate Formparanate Methiocarb Methomyl Metolcarb Miotine Oxamyl Phenmedipham Pinmicarb Pirimicarb Propamocarb Propham Propoxur Thiofanox; Stigmines: Distigmine Eptastigmine Ganstigmine Neostigmine Phenserine Physostigmine Pyridostigmine Quilostigmine Rivastigmine Terestigmine; Others: Acotiamide Ambenonium Caffeine Donepezil EA-3990 EA-4056 Edrophonium Galantamine Huperzine A Ipidacrine Itopride Ladostigil Minaprine T-1123 Tacrine Zanapezil

Irreversible: Organophosphates: Acephate Anatoxin-a(S) Azinphos-ethyl Azinphos-methyl BAY-29952 Bensulide Cadusafos Carbophenothion Chlorethoxyfos Chlorfenvinphos Chlorpyrifos Chlorpyrifos-methyl Coumaphos Cyanophos Cyclosarin Demephion Demeton Demeton-S-methyl Dialifor Diazinon Dichlorvos Dicrotophos Diisopropyl fluorophosphate Diisopropylphosphate Dimefox Dimethoate Dimethyl 4-(methylthio)phenyl phosphate Dioxathion Disulfoton EA-3148 Echothiophate Endothion Ethion Ethoprop Fenamiphos Fenitrothion Fenthion Fonofos Formothion Fosthiazate GV Hexaethyl tetraphosphate Isofluorophate Isoxathion Leptophos Malaoxon Malathion Methamidophos Methidathion Methyl phenkapton Metrifonate Mevinphos Monocrotophos Naled Novichok agent Omethoate Oxydemeton-methyl Paraoxon Parathion Parathion-methyl Phorate Phosalone Phosfolan Phosmet Phosphamidon Phoxim Pirimiphos-methyl Profenofos Prothoate Sarin Soman Tabun Tebupirimfos Temefos Terbufos Tetrachlorvinphos Triazofos Tribufos Trichlorfon Trichloronate Tricresyl phosphate VE VG VM VR VX; Others: Demecarium Fasciculins (green mamba toxins) (1, 2, 3, 4) Onchidal
Onchidal
(Onchidella binneyi)

Unsorted: α-Pinene α-Viniferin Affinine Affinisine Arisugacin A Bulbocapnine Conodurine Coronaridine Corydaline Corynoline Crimidine Cyclanoline Cymserine Harmaline Kobophenol A Lactucopicrin Phosacetim Rosmarinic acid Stercuronium iodide Taspine Tetrahydrocannabinol Ungeremine Ungiminorine

Reactivators: Asoxime chloride Methoxime Obidoxime Pralidoxime Trimedoxime bromide

BChE

Inhibitors: Affinine Affinisine Conodurine Cymserine Ladostigil Profenamine
Profenamine
(ethopropazine) Rivastigmine Tacrine ZINC-12613047 Many of the other AChE inhibitors listed above

Transporter (modulators)

CHT

Inhibitors: Hemicholinium-3
Hemicholinium-3
(hemicholine) Triethylcholine

Enhancers: Coluracetam

VAChT

Inhibitors: Vesamicol

Release (modulators)

Inhibitors

SNAP-25 inactivators: Botulinum toxin
Botulinum toxin
(A, C, E)

VAMP inactivators: Botulinum toxin
Botulinum toxin
(B, D, F, G)

Others: Bungarotoxins (β-bungarotoxin, γ-bungarotoxin)

Enhancers

LPHN agonists: α-Latrotoxin

Others: Atracotoxin
Atracotoxin
(e.g., robustoxin, versutoxin) Crotoxin

See also: Receptor/signaling modulators • Muscarinic acetylcholine receptor modulators • Nicotinic acetylcholine receptor modulators

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Food safety

Adulterants, food contaminants

3-MCPD Aldicarb Cyanide Formaldehyde Lead poisoning Melamine Mercury in fish Sudan I

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Microorganisms

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Parasitic infections through food

Amoebiasis Anisakiasis Cryptosporidiosis Cyclosporiasis Diphyllobothriasis Enterobiasis Fasciolopsiasis Fasciolosis Giardiasis Gnathostomiasis Paragonimiasis Toxoplasmosis Trichinosis Trichuriasis

Pesticides

Chlorpyrifos DDT Lindane Malathion Methamidophos

Preservatives

Benzoic acid Ethylenediaminetetraacetic acid
Ethylenediaminetetraacetic acid
(EDTA) Sodium benzoate

Sugar
Sugar
substitutes

Acesulfame potassium Aspartame Saccharin Sodium cyclamate Sorbitol Sucralose

Toxins, poisons, environment pollution

Aflatoxin Arsenic contamination of groundwater Benzene in soft drinks Bisphenol A Dieldrin Diethylstilbestrol Dioxin Mycotoxins Nonylphenol Shellfish poisoning

Food contamination incidents

Devon colic Swill milk scandal 1858 Bradford sweets poisoning 1900 English beer poisoning Morinaga Milk arsenic poisoning incident Minamata disease 1971 Iraq poison grain disaster Toxic oil syndrome 1993 Jack in the Box E. coli outbreak 1996 Odwalla E. coli outbreak 2006 North American E. coli outbreaks ICA meat repackaging controversy 2008 Canada listeriosis outbreak 2008 Chinese milk scandal 2008 Irish pork crisis 2008 United States salmonellosis outbreak 2011 Germany E. coli outbreak 2011 Taiwan food scandal 2011 United States listeriosis outbreak 2013 Bihar school meal poisoning 2013 horse meat scandal 2013 Taiwan food scandal 2014 Taiwan food scandal 2017 Brazil weak meat scandal 2017–18 South African listeriosis outbreak Food safety
Food safety
incidents in China Foodborne illness

outbreaks death toll United States

Regulation, standards, watchdogs

Acceptable daily intake E number Food labeling regulations Food libel laws International Food Safety Network ISO 22000 Quality Assurance International

Institutions

Centre for Food Safety European Food Safety Authority Institute for Food Safety and Health International Food Safety Network Ministry of Food and Drug Safety

Authority control

LCCN: sh91004490 GND: 4224448-1 N

.