This article is about the organic derivatives of the phosphate ion. For the inorganic ion, see phosphate. For all organic compound incorporating phosphorus, see organophosphorus chemistry.
General chemical structure of the organophosphate functional group
In organic chemistry, organophosphates (also known as phosphate esters, or OPEs) are a class of organophosphorus compounds with the general structure O=P(OR)3, a central phosphate molecule with alkyl or aromatic substituents.[1] They can be considered as esters of phosphoric acid. Organophosphates are best known for their use as pesticides.
Like most functional groups, organophosphates occur in a diverse range of forms,[2] with important examples including key biomolecules such as DNA, RNA and ATP, as well as many insecticides, herbicides, nerve agents and flame retardants. OPEs have been widely used in various products as flame retardants, plasticizers, and performance additives to engine oil. The low cost of production and compatibility to diverse polymers made OPEs to be widely used in industry including textile, furniture, electronics as plasticizers and flame retardants. These compounds are added to the final product physically rather than by chemical bond.[3] Due to this, OPEs leak into the environment more readily through volatilization, leaching, and abrasion.[4] OPEs have been detected in diverse environmental compartments such as air, dust, water, sediment, soil and biota samples at higher frequency and concentration.[1][4]
The popularity of OPEs as flame retardants came as a substitution for the highly regulated brominated flame retardants.[5]
^ abGreaves, Alana K.; Letcher, Robert J.; Chen, Da; McGoldrick, Daryl J.; Gauthier, Lewis T.; Backus, Sean M. (2016-10-01). "Retrospective analysis of organophosphate flame retardants in herring gull eggs and relation to the aquatic food web in the Laurentian Great Lakes of North America". Environmental Research. 150: 255–263. Bibcode:2016ER....150..255G. doi:10.1016/j.envres.2016.06.006. ISSN 0013-9351. PMID 27322497.
^Ung, Sosthène P.-M.; Li, Chao-Jun (2023). "From rocks to bioactive compounds: a journey through the global P( v ) organophosphorus industry and its sustainability". RSC Sustainability. 1 (1): 11–37. doi:10.1039/D2SU00015F.
^Wang, Xiaolei; Zhong, Wenjue; Xiao, Bowen; Liu, Qing; Yang, Liping; Covaci, Adrian; Zhu, Lingyan (2019-04-01). "Bioavailability and biomagnification of organophosphate esters in the food web of Taihu Lake, China: Impacts of chemical properties and metabolism". Environment International. 125: 25–32. doi:10.1016/j.envint.2019.01.018. hdl:10067/1585250151162165141. ISSN 0160-4120. PMID 30690428.
In organic chemistry, organophosphates (also known as phosphate esters, or OPEs) are a class of organophosphorus compounds with the general structure O=P(OR)3...
Organophosphate poisoning is poisoning due to organophosphates (OPs). Organophosphates are used as insecticides, medications, and nerve agents. Symptoms...
Aryldialkylphosphatase (EC 3.1.8.1, also known as phosphotriesterase, organophosphate hydrolase, parathion hydrolase, paraoxonase, and parathion aryl esterase;...
compounds called oximes that bind to organophosphate-inactivated acetylcholinesterase. It is used to treat organophosphate poisoning in conjunction with atropine...
Malathion is an organophosphate insecticide which acts as an acetylcholinesterase inhibitor. In the USSR, it was known as carbophos, in New Zealand and...
irreversible, or quasi-irreversible (also called pseudo-irreversible). Organophosphates like TEPP and sarin inhibit cholinesterases, enzymes that hydrolyze...
exposure to sub-lethal amounts of organophosphates, particularly sarin. Exposure to pesticides containing other organophosphates and exposure to pills containing...
physicians for these purposes. Atropine is not an actual antidote for organophosphate poisoning. However, by blocking the action of acetylcholine at muscarinic...
orthophosphate In organic chemistry, phosphate or orthophosphate is an organophosphate, an ester of orthophosphoric acid of the form PO 4RR′R″ where one or...
Acephate is an organophosphate foliar and soil insecticide of moderate persistence with residual systemic activity of about 10–15 days at the recommended...
toxaphene). Organophosphates are another large class of contact insecticides. These also target the insect's nervous system. Organophosphates interfere...
remarkable side effects. Huperzine A might be useful in the treatment of organophosphate nerve agent poisoning by preventing damage to the central nervous system...
Pharmaceutical, Shire, and Takeda Pharmaceutical Company. The toxicity of organophosphates results primarily from their action as irreversible inhibitors of...
as pesticides around the world. In most respects, it is similar to organophosphate poisoning, though typically less severe or requiring a larger amount...
chemistry, chlorpyrifos (CPS), also known as chlorpyrifos ethyl, is an organophosphate pesticide that has been used on crops, animals, and buildings, and...
biphenyls, may develop problems which resemble ADHD. Exposure to the organophosphate insecticides chlorpyrifos and dialkyl phosphate is associated with...
disease [COPD]) Sinus bradycardia due to a hypersensitive vagus nerve Organophosphate based nerve agent poisoning, such as VX, sarin, tabun, and soman (atropine...
used in civilian laboratories to mimic lethal nerve gas exposure or organophosphate toxicities. It has also been used to develop a rodent model of Gulf...
Parathion S is an organophosphate related to the organophosphate insecticide paraoxon and parathion. It's the structural isomer of parathion. Parathion...
Chemical Industries (ICI) was investigating a class of organophosphate compounds (organophosphate esters of substituted aminoethanethiols). Like Schrader...
spinal cord. The resulting type of paralysis is now referred to as organophosphate-induced delayed neuropathy, or OPIDN. In 1930, large numbers of Jake...
chemical company (later Novartis and then Syngenta). It is a nonsystemic organophosphate insecticide formerly used to control cockroaches, silverfish, ants...
compound with the formula OP(OC6H5)3. It is the simplest aromatic organophosphate. This colourless solid is the ester (triester) of phosphoric acid and...
series of convulsive spasms. Common mnemonics for the symptomatology of organophosphate poisoning, including sarin, are the "killer Bs" of bronchorrhea and...
conglomerate IG Farben, he was experimenting with a class of compounds called organophosphates, which killed insects by interrupting their nervous systems. Schrader...
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