Parathion, also called parathion-ethyl or diethyl parathion, is an

organophosphate In organic chemistry, organophosphates (also known as phosphate esters, or OPEs) are a class of organophosphorus compounds with the general structure , a central phosphate molecule with alkyl or aromatic substituents. They can be considered ...

insecticide Insecticides are pesticides used to kill insects. They include ovicides and larvicides used against insect eggs and larvae, respectively. The major use of insecticides is in agriculture, but they are also used in home and garden settings, i ...

and

acaricide Acaricides are pesticides that kill members of the arachnid subclass '' Acari'', which includes ticks and mites. Acaricides are used both in medicine and agriculture, although the desired selective toxicity differs between the two fields. Termi ...

. It was originally developed by

IG Farben I. G. Farbenindustrie AG, commonly known as IG Farben, was a German Chemical industry, chemical and Pharmaceutical industry, pharmaceutical conglomerate (company), conglomerate. It was formed on December 2, 1925 from a merger of six chemical co ...

in the 1940s. It is highly toxic to non-target organisms, including humans, so its use has been banned or restricted in most countries. In response to safety concerns, the less toxic but still dangerous analogue

parathion methyl Parathion methyl, or methyl parathion, is an organophosphate insecticide, possessing an organothiophosphate group. It is structurally very similar to parathion-ethyl. It is not allowed for sale and import in nearly all countries around the world, ...

was later developed.

History

Parathion was developed by

Gerhard Schrader Gerhard Schrader (25 February 1903 – 10 April 1990) was a German chemist specializing in the discovery of new insecticides, hoping to make progress in the fight against hunger in the world. Schrader is best known for his accidental discovery of ...

for the German trust

in the 1940s. After

World War II World War II or the Second World War (1 September 1939 – 2 September 1945) was a World war, global conflict between two coalitions: the Allies of World War II, Allies and the Axis powers. World War II by country, Nearly all of the wo ...

and the collapse of IG Farben due to the war crime trials, the Western allies seized the

patent A patent is a type of intellectual property that gives its owner the legal right to exclude others from making, using, or selling an invention for a limited period of time in exchange for publishing an sufficiency of disclosure, enabling discl ...

, 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 E numbers, short for Europe numbers, are codes for substances used as food additives, including those found naturally in many foods, such as vitamin C, for use within the European Union (EU) and European Free Trade Association (EFTA). Commonly ...

" as used in the EU today. "E" stands for ''Entwicklungsnummer'' (German for "development number"). It is an irreversible

acetylcholinesterase inhibitor Acetylcholinesterase inhibitors (AChEIs) also often called cholinesterase inhibitors, inhibit the enzyme acetylcholinesterase from breaking down the neurotransmitter acetylcholine into choline and acetate, thereby increasing both the level an ...

. Safety concerns later led to the development of

, which is somewhat less toxic. In the EU, Parathion was banned after 2001. In

Switzerland Switzerland, officially the Swiss Confederation, is a landlocked country located in west-central Europe. It is bordered by Italy to the south, France to the west, Germany to the north, and Austria and Liechtenstein to the east. Switzerland ...

, the substance is no longer approved as a pesticide.

Handling properties

Pure parathion is a white crystalline solid. It is commonly distributed as a brown

liquid Liquid is a state of matter with a definite volume but no fixed shape. Liquids adapt to the shape of their container and are nearly incompressible, maintaining their volume even under pressure. The density of a liquid is usually close to th ...

that smells of rotting

egg An egg is an organic vessel grown by an animal to carry a possibly fertilized egg cell (a zygote) and to incubate from it an embryo within the egg until the embryo has become an animal fetus that can survive on its own, at which point the ...

s or

garlic Garlic (''Allium sativum'') is a species of bulbous flowering plants in the genus '' Allium''. Its close relatives include the onion, shallot, leek, chives, Welsh onion, and Chinese onion. Garlic is native to central and south Asia, str ...

. The insecticide is somewhat stable, although it darkens when exposed to sunlight.

Industrial synthesis

Parathion is synthesized from

diethyl dithiophosphoric acid Diethyl dithiophosphoric acid, sometimes mistakenly called diethyl dithiophosphate, is the organophosphorus compound with the formula (C2H5O)2PS2H. It is the processor for production of the organophosphate insecticide Terbufos. Although samples ...

by chlorination to generate diethylthiophosphoryl chloride (), and then the chloride is treated with sodium 4-nitrophenolate (the

sodium Sodium is a chemical element; it has Symbol (chemistry), symbol Na (from Neo-Latin ) and atomic number 11. It is a soft, silvery-white, highly reactive metal. Sodium is an alkali metal, being in group 1 element, group 1 of the peri ...

salt In common usage, salt is a mineral composed primarily of sodium chloride (NaCl). When used in food, especially in granulated form, it is more formally called table salt. In the form of a natural crystalline mineral, salt is also known as r ...

4-nitrophenol 4-Nitrophenol (also called ''p''-nitrophenol or 4-hydroxynitrobenzene) is a phenolic compound that has a nitro group at the opposite position of the hydroxyl group on the benzene ring. Properties 4-nitro phenol is a slightly yellow, crystalline ...

). : :

Applications

As a pesticide, parathion is generally applied by spraying. It is often applied to

cotton Cotton (), first recorded in ancient India, is a soft, fluffy staple fiber that grows in a boll, or protective case, around the seeds of the cotton plants of the genus '' Gossypium'' in the mallow family Malvaceae. The fiber is almost pure ...

rice Rice is a cereal grain and in its Domestication, domesticated form is the staple food of over half of the world's population, particularly in Asia and Africa. Rice is the seed of the grass species ''Oryza sativa'' (Asian rice)—or, much l ...

and

fruit In botany, a fruit is the seed-bearing structure in flowering plants (angiosperms) that is formed from the ovary after flowering. Fruits are the means by which angiosperms disseminate their seeds. Edible fruits in particular have long propaga ...

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.

Insecticidal activity

Parathion acts on the enzyme

acetylcholinesterase Acetylcholinesterase (HUGO Gene Nomenclature Committee, HGNC symbol ACHE; EC 3.1.1.7; systematic name acetylcholine acetylhydrolase), also known as AChE, AChase or acetylhydrolase, is the primary cholinesterase in the body. It is an enzyme th ...

indirectly. After an insect (or a human) ingests parathion, an

oxidase In biochemistry, an oxidase is an oxidoreductase (any enzyme that catalyzes a redox reaction) that uses dioxygen (O2) as the electron acceptor. In reactions involving donation of a hydrogen atom, oxygen is reduced to water (H2O) or hydrogen peroxid ...

replaces the double bonded sulfur with oxygen to give

paraoxon Paraoxon is a parasympathomimetic drug which acts as an cholinesterase inhibitor. It is an organophosphate oxon, and the active metabolite of the insecticide parathion. It is also used as an ophthalmological drug against glaucoma. Paraoxon is o ...

. : The phosphate ester is more reactive in organisms than the phosphorothiolate ester, as the phosphorus atoms become much more electropositive. Parathion is a special case of

acetylcholinesterase inhibitor resistance Acetylcholinesterase inhibitors (AChEIs) also often called cholinesterase inhibitors, inhibit the enzyme acetylcholinesterase from breaking down the neurotransmitter acetylcholine into choline and acetate, thereby increasing both the level and ...

Degradation

Degradation of parathion leads to more water-soluble products.

Hydrolysis Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution reaction, substitution, elimination reaction, elimination, and solvation reactions in which water ...

, which deactivates the molecule, occurs at the aryl ester bond resulting in diethyl thiophosphate and

. : Degradation proceeds differently under

anaerobic Anaerobic means "living, active, occurring, or existing in the absence of free oxygen", as opposed to aerobic which means "living, active, or occurring only in the presence of oxygen." Anaerobic may also refer to: *Adhesive#Anaerobic, Anaerobic ad ...

conditions: the nitro group on parathion is reduced to the

amine In chemistry, amines (, ) are organic compounds that contain carbon-nitrogen bonds. Amines are formed when one or more hydrogen atoms in ammonia are replaced by alkyl or aryl groups. The nitrogen atom in an amine possesses a lone pair of elec ...

. :

Safety

Parathion is a

cholinesterase inhibitor Cholinesterase inhibitors (ChEIs), also known as anti-cholinesterase, are chemicals that prevent the breakdown of the neurotransmitter acetylcholine or butyrylcholine by cholinesterase. This increases the amount of the acetylcholine or butyryl ...

. It generally disrupts the

nervous system In biology, the nervous system is the complex system, highly complex part of an animal that coordinates its behavior, actions and sense, sensory information by transmitting action potential, signals to and from different parts of its body. Th ...

by inhibiting

. 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

headache A headache, also known as cephalalgia, is the symptom of pain in the face, head, or neck. It can occur as a migraine, tension-type headache, or cluster headache. There is an increased risk of Depression (mood), depression in those with severe ...

convulsions A convulsion is a medical condition where the body muscles contract and relax rapidly and repeatedly, resulting in uncontrolled shaking. Because epileptic seizures typically include convulsions, the term ''convulsion'' is often used as a synony ...

, poor vision,

vomiting Vomiting (also known as emesis, puking and throwing up) is the forceful expulsion of the contents of one's stomach through the mouth and sometimes the nose. Vomiting can be the result of ailments like food poisoning, gastroenteritis, pre ...

, abdominal pain, severe

diarrhea Diarrhea (American English), also spelled diarrhoea or diarrhœa (British English), is the condition of having at least three loose, liquid, or watery bowel movements in a day. It often lasts for a few days and can result in dehydration d ...

unconsciousness Unconsciousness is a state in which a living individual exhibits a complete, or near-complete, inability to maintain an awareness of self and environment or to respond to any human or environmental stimulus. Unconsciousness may occur as the r ...

tremor A tremor is an involuntary, somewhat rhythmic muscle contraction and relaxation involving neural oscillations, oscillations or twitching movements of one or more body parts. It is the most common of all involuntary movements and can affect the h ...

dyspnea Shortness of breath (SOB), known as dyspnea (in AmE) or dyspnoea (in BrE), is an uncomfortable feeling of not being able to breathe well enough. The American Thoracic Society defines it as "a subjective experience of breathing discomfort that ...

, and finally

pulmonary edema Pulmonary edema (British English: oedema), also known as pulmonary congestion, is excessive fluid accumulation in the tissue or air spaces (usually alveoli) of the lungs. This leads to impaired gas exchange, most often leading to shortness ...

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 Atropine is a tropane alkaloid and anticholinergic medication used to treat certain types of nerve agent and pesticide poisonings as well as some types of slow heart rate, and to decrease saliva production during surgery. It is typically give ...

, 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 Cerebral hypoxia is a form of Hypoxia (medical), hypoxia (reduced supply of oxygen), specifically involving the human brain, brain; when the brain is completely deprived of oxygen, it is called ''cerebral anoxia''. There are four categories of c ...

and permanent brain damage.

Peripheral neuropathy Peripheral neuropathy, often shortened to neuropathy, refers to damage or disease affecting the nerves. Damage to nerves may impair sensation, movement, gland function, and/or organ function depending on which nerve fibers are affected. Neuropa ...

including

paralysis Paralysis (: paralyses; also known as plegia) is a loss of Motor skill, motor function in one or more Skeletal muscle, muscles. Paralysis can also be accompanied by a loss of feeling (sensory loss) in the affected area if there is sensory d ...

is noticed as late

sequelae A sequela (, ; usually used in the plural, sequelae ) is a pathological condition resulting from a disease, injury, therapy, or other trauma. Derived from the Latin word meaning "sequel", it is used in the medical field to mean a complication or c ...

after recovery from acute intoxication. Parathion and related organophosphorus pesticides are used in hundreds of thousands of poisonings annually, especially suicides. 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 The British South Africa Police (BSAP) was, for most of its existence, the police force of Southern Rhodesia and Rhodesia (renamed Zimbabwe in 1980). It was formed as a paramilitary force of mounted infantrymen in 1889 by Cecil Rhodes' Britis ...

attached to the

Selous Scouts The Selous Scouts was a special forces unit of the Rhodesian Army that operated during the Rhodesian Bush War from 1973 until the reconstitution of the country as Zimbabwe in 1980. It was mainly responsible for infiltrating the black majority ...

during the

Rhodesian Bush War The Rhodesian Bush War, also known as the Rhodesian Civil War, Second as well as the Zimbabwe War of Independence, was a civil conflict from July 1964 to December 1979 in the List of states with limited recognition, unrecognised country U.D.I. ...

. 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. Based on animal studies, parathion is considered by the

U.S. Environmental Protection Agency The Environmental Protection Agency (EPA) is an independent agency of the United States government tasked with environmental protection matters. President Richard Nixon proposed the establishment of EPA on July 9, 1970; it began operation on De ...

to be a possible human

carcinogen A carcinogen () is any agent that promotes the development of cancer. Carcinogens can include synthetic chemicals, naturally occurring substances, physical agents such as ionizing and non-ionizing radiation, and biologic agents such as viruse ...

. Studies show that parathion is toxic to fetuses, but does not cause birth defects. It is classified by the

United Nations Environment Programme The United Nations Environment Programme (UNEP) is responsible for coordinating responses to environmental issues within the United Nations system. It was established by Maurice Strong, its first director, after the Declaration of the United Nati ...

as a

persistent organic pollutant Persistent organic pollutants (POPs) are organic compounds that are resistant to degradation through chemical, biological, and photolytic processes. They are toxic and adversely affect human health and the environment around the world. Because ...

and by the

World Health Organization The World Health Organization (WHO) is a list of specialized agencies of the United Nations, specialized agency of the United Nations which coordinates responses to international public health issues and emergencies. It is headquartered in Gen ...

as Toxicity Class Ia (extremely hazardous). Parathion is toxic to

bees Bees are winged insects closely related to wasps and ants, known for their roles in pollination and, in the case of the best-known bee species, the western honey bee, for producing honey. Bees are a monophyletic lineage within the superfamil ...

fish A fish (: fish or fishes) is an aquatic animal, aquatic, Anamniotes, anamniotic, gill-bearing vertebrate animal with swimming fish fin, fins and craniate, a hard skull, but lacking limb (anatomy), limbs with digit (anatomy), digits. Fish can ...

bird Birds are a group of warm-blooded vertebrates constituting the class (biology), class Aves (), characterised by feathers, toothless beaked jaws, the Oviparity, laying of Eggshell, hard-shelled eggs, a high Metabolism, metabolic rate, a fou ...

s, and other forms of wildlife.

Protection against poisoning

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 Occupational safety and health (OSH) or occupational health and safety (OHS) is a multidisciplinary field concerned with the safety, health, and quality of life, welfare of people at Work (human activity), work (i.e., while performing duties re ...

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.

Use in suicides

A chemist swallowed of parathion 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. Parathion was commonly used for suicides in the 1950s and 1960s.

References

External links

*
ATSDR - Methyl Parathion Expert Panel Report
U.S.

Department of Health and Human Services The United States Department of Health and Human Services (HHS) is a cabinet-level executive branch department of the US federal government created to protect the health of the US people and providing essential human services. Its motto is ...

(public domain)
CDC - NIOSH Pocket Guide to Chemical Hazards
U.S.

(public domain) * Ethyl parathion: * Methyl parathion: {{Authority control Obsolete pesticides Organophosphate insecticides Acetylcholinesterase inhibitors Organothiophosphate esters 4-Nitrophenyl compounds IARC Group 2B carcinogens Phenol esters Ethyl esters