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Organophosphate : ウィキペディア英語版
Organophosphate

An organophosphate (sometimes abbreviated OP) or phosphate ester is the general name for esters of phosphoric acid. Many of the most important biochemicals are organophosphates, including DNA and RNA as well as many cofactors that are essential for life. Organophosphates are the basis of many insecticides, herbicides, and nerve agents. The United States Environmental Protection Agency lists organophosphates as very highly acutely toxic to bees, wildlife, and humans. Recent studies suggest a possible link to adverse effects in the neurobehavioral development of fetuses and children, even at very low levels of exposure. Organophosphates are widely used as solvents, plasticizers, and EP additives.
Organophosphates are widely employed both in natural and synthetic applications because of the ease with which organic groups can be linked together.
:OP(OH)3 + ROH → OP(OH)2(OR) + H2O
:OP(OH)2(OR) + R'OH → OP(OH)(OR)(OR') + H2O
:OP(OH)(OR)(OR') + R"OH → OP(OR)(OR')(OR") + H2O
The phosphate esters bearing OH groups are acidic and partially deprotonated in aqueous solution. For example, DNA and RNA are polymers of the type ()n. Polyphosphates also form esters; an important example of an ester of a polyphosphate is ATP, which is the monoester of triphosphoric acid (H5P3O10).
Alcohols can be detached from phosphate esters by hydrolysis, which is the reverse of the above reactions. For this reason, phosphate esters are common carriers of organic groups in biosynthesis.
== Organophosphate pesticides ==
In health, agriculture, and government, the word "organophosphates" refers to a group of insecticides or nerve agents acting on the enzyme acetylcholinesterase (the pesticide group carbamates also act on this enzyme, but through a different mechanism). The term is used often to describe virtually any organic phosphorus(V)-containing compound, especially when dealing with neurotoxic compounds. Many of the so-called organophosphates contain C-P bonds. For instance, sarin is ''O''-isopropyl methylphosphonofluoridate, which is formally derived from phosphorous acid (HP(O)(OH)2), not phosphoric acid (P(O)(OH)3). Also, many compounds which are derivatives of phosphinic acid are used as neurotoxic organophosphates.
Organophosphate pesticides (as well as sarin and VX nerve agent) irreversibly inactivate acetylcholinesterase, which is essential to nerve function in insects, humans, and many other animals. Organophosphate pesticides affect this enzyme in varied ways, and thus in their potential for poisoning. For instance, parathion, one of the first OPs commercialized, is many times more potent than malathion, an insecticide used in combatting the Mediterranean fruit fly (Med-fly) and West Nile Virus-transmitting mosquitoes.
Organophosphate pesticides degrade rapidly by hydrolysis on exposure to sunlight, air, and soil, although small amounts can be detected in food and drinking water. Their ability to degrade made them an attractive alternative to the persistent organochloride pesticides, such as DDT, aldrin, and dieldrin. Although organophosphates degrade faster than the organochlorides, they have greater acute toxicity, posing risks to people who may be exposed to large amounts (see the Toxicity section below).
Commonly used organophosphates have included parathion, malathion, methyl parathion, chlorpyrifos, diazinon, dichlorvos, phosmet, fenitrothion, tetrachlorvinphos, azamethiphos, and azinphos-methyl. Malathion is widely used in agriculture, residential landscaping, public recreation areas, and in public health pest control programs such as mosquito eradication.〔(Malathion for mosquito control ), US EPA〕 In the US, it is the most commonly used organophosphate insecticide. Forty organophosphate pesticides are registered in the U.S., with at least 73 million pounds used in agricultural and residential settings.

They are of concern to both scientists and regulators because they work by irreversibly blocking an enzyme that's critical to nerve function in both insects and humans. Even at relatively low levels, organophosphates may be most hazardous to the brain development of fetuses and young children. The EPA banned most residential uses of organophosphates in 2001, but they are still sprayed agriculturally on fruits and vegetables. They're also used to control pests like mosquitos in public spaces such as parks. They can be absorbed through the lungs or skin or by eating them on food.

抄文引用元・出典: フリー百科事典『 ウィキペディア(Wikipedia)
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