:Parathion

File:E605-forte.jpg

Parathion was developed by Gerhard Schrader for the German trust IG Farben in the 1940s. After World War II and the collapse of IG Farben due to the war crime trials, the Western allies seized the patent, and parathion was marketed worldwide by different companies and under different brand names. The most common German brand was E605 (banned in Germany after 2002); this was not a food-additive "E number" as used in the EU today. "E" stands for Entwicklungsnummer (German for "development number"). It is an irreversible acetylcholinesterase inhibitor.

Safety concerns later led to the development of parathion methyl, which is somewhat less toxic.

In the EU, Parathion was banned after 2001. [https://eur-lex.europa.eu/legal-content/EN/TXT/PDF/?uri=CELEX:32001D0520&from=DE Non-inclusion of parathion in Annex I to Council Directive 91/414/EEC] In Switzerland, the substance is no longer approved as a pesticide.

Pure parathion is a white crystalline solid. It is commonly distributed as a brown liquid that smells of rotting eggs or garlic. The insecticide is somewhat stable, although it darkens when exposed to sunlight.

Parathion is synthesized from diethyl dithiophosphoric acid {{chem2|(C2H5O)2PS2H}} by chlorination to generate diethylthiophosphoryl chloride ({{chem2|(C2H5O)2P(S)Cl}}), and then the chloride is treated with sodium 4-nitrophenolate (the sodium salt of 4-nitrophenol).{{cite book |last1=Fee |first1=D. C. |last2=Gard |first2=D. R. |last3=Yang |first3=C. |chapter=Phosphorus Compounds |title=Kirk-Othmer Encyclopedia of Chemical Technology |publisher=John Wiley & Sons |location=New York |year=2005 |doi=10.1002/0471238961.16081519060505.a01.pub2 |isbn=978-0471238966 }}

:{{chem2|2 (C2H5O)2P(S)SH + 3 Cl2 → 2 (C2H5O)2P(S)Cl + S2Cl2 + 2 HCl}}

:{{chem2|(C2H5O)2P(S)Cl + NaOC6H4NO2 → (C2H5O)2P(S)OC6H4NO2 + NaCl}}

As a pesticide, parathion is generally applied by spraying. It is often applied to cotton, rice and fruit trees. The usual concentrations of ready-to-use solutions are 0.05 to 0.1%. The chemical is banned for use on many food crops.

Parathion acts on the enzyme acetylcholinesterase indirectly. After an insect (or a human) ingests parathion, an oxidase replaces the double bonded sulfur with oxygen to give paraoxon.{{cite book |last=Metcalf |first=R. L. |chapter=Insect Control |title=Ullmann's Encyclopedia of Industrial Chemistry |publisher=Wiley-VCH Verlag GmbH & Co. KGaA |location=New York |year=2002 |doi=10.1002/14356007.a14_263 |isbn=978-3527306732 }}

:{{chem2|(C2H5O)2P(S)OC6H4NO2 + 1/2 O2 → (C2H5O)2P(O)OC6H4NO2 + S}}

The phosphate ester is more reactive in organisms than the phosphorothiolate ester, as the phosphorus atoms become much more electropositive.

Parathion {{visible anchor|Resistance|text=resistance}} is a special case of acetylcholinesterase inhibitor resistance.

Degradation of parathion leads to more water-soluble products. Hydrolysis, which deactivates the molecule, occurs at the aryl ester bond resulting in diethyl thiophosphate and 4-nitrophenol.

:{{chem2|(C2H5O)2P(S)OC6H4NO2 + H2O → HOC6H4NO2 + (C2H5O)2P(S)OH}}

Degradation proceeds differently under anaerobic conditions: the nitro group on parathion is reduced to the amine.

:{{chem2|(C2H5O)2P(S)OC6H4NO2 + 6 H → (C2H5O)2P(S)OC6H4NH2 + 2 H2O}}

Parathion is a cholinesterase inhibitor. It generally disrupts the nervous system by inhibiting acetylcholinesterase. It is absorbed via skin, mucous membranes, and orally. Absorbed parathion is rapidly metabolized to paraoxon, as described in Insecticidal activity. Paraoxon exposure can result in headaches, convulsions, poor vision, vomiting, abdominal pain, severe diarrhea, unconsciousness, tremor, dyspnea, and finally pulmonary edema as well as respiratory arrest. Symptoms of poisoning are known to last for extended periods, sometimes months. The most common and very specific antidote is atropine, in doses of up to 100 mg daily. Because atropine may also be toxic, it is recommended that small frequently repeated doses be used in treatment. If human poisoning is detected early and the treatment is prompt (atropine and artificial respiration), fatalities are infrequent. Insufficient oxygen will lead to cerebral hypoxia and permanent brain damage. Peripheral neuropathy including paralysis is noticed as late sequelae after recovery from acute intoxication. Parathion and related organophosphorus pesticides are used in hundreds of thousands of poisonings annually, especially suicides.Litchfield, M.H. "Estimates of acute pesticide poisoning in agricultural workers in less developed countries" Toxicology Reviews 2005, volume 24, pp. 271-8. {{PMID|16499408}} It is known as Schwiegermuttergift (mother-in-law poison) in Germany. For this reason, most formulations contain a blue dye providing warning.

Parathion was used as a chemical warfare agent, most notably by an element of the British South Africa Police attached to the Selous Scouts during the Rhodesian Bush War. They used it to poison clothing that was then supplied to anti-government guerrillas. When the enemy soldiers put on the clothes, they were poisoned by absorption through the skin.{{Cite web|url=https://openaccess.leidenuniv.nl/bitstream/handle/1887/68698/Poison%20in%20Rhodesia%2C%20Colm%20Wittenberg.pdf?sequence=1|title = Poison in Rhodesia|date = 31 January 2019}}{{Cite web|url=http://cco.ndu.edu/News/Article/1506904/dirty-war-rhodesia-and-chemical-biological-warfare-1975-1980-book-review/|title=Dirty War: Rhodesia and Chemical Biological Warfare 1975-1980 (Book Review)|website=PRISM | National Defense University}}{{cite book|title=Dirty War: Rhodesia and Chemical Biological Warfare, 1975–1980|last=Cross|first=Glenn|year=2017|location=Solihull, UK|publisher=Helion & Company|isbn=978-1-911512-12-7}}

Based on animal studies, parathion is considered by the U.S. Environmental Protection Agency to be a possible human carcinogen.{{cite web | title = Parathion | work = Integrated Risk Information System | publisher = U. S. Environmental Protection Agency | date = 26 January 2007 | url = http://www.epa.gov/iris/subst/0327.htm}} Studies show that parathion is toxic to fetuses, but does not cause birth defects.{{cite web | work = Extension Toxicology Network | title = Pesticide Information Profiles - Parathion | publisher = Oregon State University |date=September 1993 | url = http://extoxnet.orst.edu/pips/parathio.htm}}

It is classified by the United Nations Environment Programme as a persistent organic pollutant{{cn|date=February 2018}} and by the World Health Organization as Toxicity Class Ia (extremely hazardous).{{cn|date=February 2018}}

Parathion is toxic to bees, fish, birds, and other forms of wildlife.

To provide the end user with a minimum standard of protection, suitable protective gloves, clothing, and a respirator with organic-vapour cartridges is normally worn. Industrial safety during the production process requires special ventilation and continuous measurement of air contamination in order not to exceed PEL levels, as well as careful attention to personal hygiene. Frequent analysis of workers' serum acetylcholinesterase activity is also helpful with regards to occupational safety, because the action of parathion is cumulative. Also, atropine has been used as a specific antidote.{{fact|date=January 2024}}

A chemist {{who?|date=March 2024}} swallowed {{convert|.00424|oz|g}} of parathion {{when?|date=March 2024}} to find the most lethal means of exposure to humans, intending to take an antidote afterwards, but was paralyzed and so died before he could reach it.{{Cite book |last=Carson |first=Rachel |url=http://worldcat.org/oclc/1346358856 |title=Silent Spring |publisher= HarperCollins|year=1962 |isbn=978-0-547-52762-8 |oclc=1346358856}}

Parathion was commonly used for suicides in the 1950s and 1960s.

• Pesticide toxicity to bees
• Parathion methyl

{{reflist}}

• {{PPDB|506}}
• [http://www.atsdr.cdc.gov/risk/methyl_parathion/ ATSDR - Methyl Parathion Expert Panel Report] U.S. Department of Health and Human Services (public domain)
• [https://www.cdc.gov/niosh/npg/npgd0479.html CDC - NIOSH Pocket Guide to Chemical Hazards] U.S. Department of Health and Human Services (public domain)
• Ethyl parathion: {{ICSC|0006}}
• Methyl parathion: {{ICSC|0626}}

{{Insecticides}}

{{Acetylcholine metabolism and transport modulators}}

{{Authority control}}

Category:Obsolete pesticides

Category:Organophosphate insecticides

Category:Acetylcholinesterase inhibitors

Category:Organothiophosphate esters

Category:4-Nitrophenyl compounds

Category:IARC Group 2B carcinogens

Category:Phenol esters

Category:Ethyl esters