What is an organophosphate?
Aryldialkylphosphatase
Organophosphate is the general name for esters of phosphoric acid and is one of the organophosphorus compounds. They can be found as part of insecticides, herbicides, and nerve gases, amongst others. Some less-toxic organophosphates can be used as solvents, plasticizers, and EP additives. The use of organophosphates accounts for approximately 38% of all pesticide use globally.
Glyphosate
Glyphosate (IUPAC name: "N"-(phosphonomethyl)glycine) is a broad-spectrum systemic herbicide and crop desiccant. It is an organophosphorus compound, specifically a phosphonate, which acts by inhibiting the plant enzyme 5-enolpyruvylshikimate-3-phosphate synthase. It is used to kill weeds, especially annual broadleaf weeds and grasses that compete with crops. It was discovered to be an herbicide by Monsanto chemist John E. Franz in 1970. Monsanto brought it to market for agricultural use in 1974 under the trade name Roundup. Monsanto's last commercially relevant United States patent expired in 2000.
Diphenylphosphine
Diphenylphosphine, also known as diphenylphosphane, is an organophosphorus compound with the formula (CH)PH. This foul-smelling, colorless liquid is easily oxidized in air. It is a precursor to organophosphorus ligands for use as catalysts.
Monofluorophosphate
Monofluorophosphate is an anion with the formula POF, which is a phosphate group with one oxygen atom substituted with a fluoride atom. The charge of the ion is −2. The ion resembles sulfate in size, shape and charge, and can thus form compounds with the same structure as sulfates. These include Tutton's salts and langbeinites. The most well-known compound of monofluorophosphate is sodium monofluorophosphate, commonly used in toothpaste.
Organophosphate poisoning
OP pesticide exposure occurs through inhalation, ingestion and dermal contact. Because OP pesticides disintegrate quickly in air and light, they have been considered relatively safe to consumers. However, OP residues linger on fruits and vegetables. Certain OP pesticides have been banned for use on some crops, for example methyl parathion is banned from use on some crops while permitted on others.Exposure to any one of the above-listed organophosphates occurs on a daily basis through inhalation, absorption, and ingestion, most commonly of food that has been treated with an organophosphate herbicide or insecticide. Exposure to these chemicals can occur at public buildings, schools, residential areas, and in agricultural areas. The chemicals chlorpyrifos and malathion have been linked to reproductive effects, neurotoxicity, kidney/liver damage, and birth defects. Dichlorvos has also been linked to reproductive effects, neurotoxicity, and kidney/liver damage, as well as being a possible carcinogen.
Organophosphorus compound
Phosphate esters have the general structure P(=O)(OR) feature P(V). Such species are of technological importance as flame retardant agents, and plasticizers. Lacking a P−C bond, these compounds are in the technical sense not organophosphorus compounds but esters of phosphoric acid. Many derivatives are found in nature, such as phosphatidylcholine. Phosphate ester are synthesized by alcoholysis of phosphorus oxychloride. A variety of mixed amido-alkoxo derivatives are known, one medically significant example being the anti-cancer drug cyclophosphamide. Also derivatives containing the thiophosphoryl group (P=S) include the pesticide malathion. The organophosphates prepared on the largest scale are the zinc dithiophosphates, as additives for motor oil. Several million kilograms of this coordination complex are produced annually by the reaction of phosphorus pentasulfide with alcohols.
In the environment, these compounds break down via hydrolysis to eventually afford phosphate and the organic alcohol or amine from which they are derived.
Tris(2,4-di-tert-butylphenyl)phosphite
Tris(2,4-di-tert-butylphenyl)phosphite is an organophosphorus compound with the formula [(CH)CHO]P. This white solid is a widely used stabilizer in polymers where it functions as an antioxidant as well as other roles. The compound is a phosphite ester derived from di-tert-butylphenol.
Dipotassium phosphate
Dipotassium phosphate (KHPO) (also dipotassium hydrogen orthophosphate; potassium phosphate dibasic) is a highly water-soluble salt which is often used as a fertilizer, food additive and buffering agent. It is a common source of phosphorus and potassium.
Organophosphate
Organophosphate pesticides (OPPs), like some nerve agents, inhibit this neuromuscular enzyme, which is broadly essential for normal function in insects, but also in humans and many other animals. OPPs affect this enzyme in varied ways, a principle one being through irreversible covalent inhibition, and so create potentials for poisoning that vary in degree. The brain sends out neurotransmitters to the nerve endings in the body; organophosphates disrupt this process from occurring.This chemical, organophosphate works by disrupting the enzyme acetylcholinesterase. Acetylcholinesterase break down the acetylcholine neurotransmitter, which sends out signals to other nerve endings in the body.
Triethylphosphite
Triethylphosphite is an organophosphorus compound with the formula P(OCHCH), often abbreviated P(OEt). This colorless liquid is used as a ligand in organometallic chemistry and as a reagent in organic synthesis
Phosphate
Phosphates are the naturally occurring form of the element phosphorus, found in many phosphate minerals. In mineralogy and geology, phosphate refers to a rock or ore containing phosphate ions. Inorganic phosphates are mined to obtain phosphorus for use in agriculture and industry.
Organophosphate poisoning
Under a 1988 amendment to the Federal Insecticide, Fungicide and Rodenticide Act (FIFRA), the U.S. Environmental Protection Agency (EPA) regulates organophosphate pesticides Its focus was initially on registering pesticides for use on food crops. No pesticide can be sold in the United States before the EPA has reviewed the manufacture's application for registration and determined that the use of the product will not present an unreasonable risk to the public or the environment. In 1996, with the passage of the Food Quality Protection Act, Congress required the EPA to reassess all existing pesticide tolerances with specific consideration for children. This resulted in a 10-year review process of the health and environmental effects of all pesticides, beginning with the organophosphates. As part of that process, in 1999 the EPA announced a ban the use of organophosphate pesticide methyl parathion and significant restrictions on the use of another OP, azinphos methyl, in what they called "kid's food". The review process was concluded in 2006 and eliminated or modified thousands of other uses of pesticides. Other legislative action has been taken to protect children from the risks of organophosphates.
Phosphate
A phosphate is chemical derivative of phosphoric acid. The phosphate ion () is an inorganic chemical, the conjugate base that can form many different salts. In organic chemistry, a phosphate, or organophosphate, is an ester of phosphoric acid. Of the various phosphoric acids and phosphates, organic phosphates are important in biochemistry and biogeochemistry (and, consequently, in ecology), and inorganic phosphates are mined to obtain phosphorus for use in agriculture and industry. At elevated temperatures in the solid state, phosphates can condense to form pyrophosphates.
Phosphirene
Phosphirene is the organophosphorus compound with the formula CHPH. It is a colorless gas of no commercial value. As the simplest cyclic, unsaturated organophosphorus compound, phosphirene is the prototype of a family of related compounds that have attracted attention from researchers.
Diethyl dithiophosphoric acid
Diethyl dithiophosphoric acid, sometimes mistakenly called diethyl dithiophosphate, is the organophosphorus compound with the formula (CHO)PSH. It is the processor for production of the organophosphate insecticide Terbufos. Although samples can appear dark, it is a colorless liquid.
Diphosphenes
Diphosphene is a kind of organophosphorus compound that has a phosphorus-phosphorus double bond, denoted by R-P=P-R'. These compounds are not common but are of theoretical interest. Normally, compounds with the empirical formula RP exist as rings. However, like other multiple bonds between heavy main-group elements, P=P double bonds can be stabilized by a large steric hindrance from the substitutions. The first isolated diphosphene bis(2,4,6-tri-tert-butylphenyl)diphosphene was exemplified by Masaaki Yoshifuji and his coworkers in 1981, in which diphosphene is stabilized by two bulky phenyl group.
Organophosphate
The word "organophosphates", when appearing in communications (e.g., from the press or the government), in areas such as agriculture, the environment, and human and animal health, very often refers to a group of insecticides (pesticides) that act on the enzyme acetylcholinesterase (see also carbamates). Today, organophosphates make up about 50% of the killing agents in chemical pesticides.
Triethylphosphine
Triethylphosphine is the organophosphorus compound with the formula P(CHCH), commonly abbreviated as PEt. It is a colorless liquid with an unpleasant odor characteristic of alkylphosphines. The compound is a common ligand in organometallic chemistry.
Fructosephosphates
Fructosephosphates are sugar phosphates based upon fructose, and are common in the biochemistry of cells.
Diethyl chlorophosphate
Diethyl chlorophosphate is a chemical used as an reagent in organic synthesis for the conversion of alcohols to the corresponding diethylphosphate esters. It is a clear liquid with a fruity odor which can range in colour from colourless to light yellow. It is a corrosive, and as a cholinesterase inhibitor, highly toxic through dermal absorption.
Phosphinite
Phosphinites are organophosphorus compounds with the formula P(OR)R. They are used as ligands in homogeneous catalysis and coordination chemistry.
PON1
PON1 was first discovered through its ability to hydrolyse and therefore detoxify organophosphorus compounds which are widely used as pesticides and nerve gases. Despite decades of research it is only now becoming clear that PON1 protects humans from the acute and chronic harmful effects of these compounds Low PON1 activity found in children may increase their susceptibility to organophosphates.
Monopotassium phosphate
Monopotassium phosphate, MKP, (also potassium dihydrogenphosphate, KDP, or monobasic potassium phosphate), , is a soluble salt of potassium and the dihydrogen phosphate ion which is used as a fertilizer, a food additive and a fungicide. It is a source of phosphorus and potassium. It is also a buffering agent. When used in fertilizer mixtures with urea and ammonium phosphates, it minimizes escape of ammonia by keeping the acidity at a relatively low level.
Phosalone
Phosalone is an organophosphate chemical commonly used as an insecticide and acaricide. It is developed by Rhône-Poulenc in France but EU eliminated it from pesticide registration on December 2006.
Chlorodiisopropylphosphine
Chlorodiisopropylphosphine is an organophosphorus compound with the formula [(CH)CH]PCl. It is a colorless liquid that reacts with water and oxygen. The compound is used to prepared tertiary phosphines and phosphinite ligands.
Aminophosphine
In organophosphorus chemistry, an aminophosphine is a compound with the formula RP(NR)n where R = H or an organic substituent, and n = 0, 1, 2. At one extreme, the parent HPNH is lightly studied and fragile, but at the other extreme tris(dimethylamino)phosphine (P(NMe)) is commonly available. Intermediate members are known, such as PhPN(H)Ph. These compounds are typically colorless and reactive toward oxygen. They have pyramidal geometry at phosphorus.
Organophosphorus compound
Compounds related to phosphine oxides are the imides (RPNR') and related chalcogenides (RPE, where E = S, Se, Te). These compounds are some of the most thermally stable organophosphorus compounds.
Organophosphate
Phosphorus oxychloride reacts readily with alcohols to give organophosphates
Phanephos
Phanephos is an organophosphorus compound with the chemical formula (CH)(CHPPh) (Ph = CH). It is a white solid that is soluble in organic solvents. It is an example of a chiral C-symmetric diphosphine ligand used in asymmetric hydrogenation. Many substituents have been introduced in place of the phenyl groups, e.g., "i"-Pr, CH, etc and a variety of chiral diphosphine ligands have been reported in asymmetric catalysis since the 1960s.
Organophosphate-induced delayed neuropathy
Organophosphate-induced delayed neuropathy (OPIDN), also called organophosphate-induced delayed polyneuropathy (OPIDP), is a neuropathy caused by killing of neurons in the central nervous system, especially in the spinal cord, as a result of acute or chronic organophosphate poisoning.
Methylphosphinic acid
Methylphosphinic acid is a monobasic acid, the simplest of the phosphinic acids. A central phosphorus atom is connected to a hydroxy group, a hydrogen atom, a methyl group and an oxygen. Derivatives of methylphosphinic acid can have the phosphorus connected hydrogen atom replaced by other organic groups. In early days what is now called methylphosphonic acid was also called methylphosphinic acid.
Leptophos
Leptophos ("O"-(4-bromo-2,5-dichlorophenyl) "O"-methyl phenylphosphonothioate) belongs to the organophosphates and at room temperature it is a stable white solid. It is also known as Phosvel, Abar and Vcs 506. Leptophos was primarily used as a pesticide and fungicide. for rice, cotton, fruit and vegetables until its use was discontinued in 1975 in USA, but still sold in Sout-Eastern Asia in 1981.
Monopotassium phosphite
Monopotassium phosphite is an inorganic compound with the formula KHPO. A compositionally related compound has the formula HPO2(KHPO). Both are white solids that contain salts of the phosphite anion HPO, the conjugate base of phosphorous acid. These materials have been used in some fertilizers.
Dichlorophenylphosphine
Dichlorophenylphosphine is an organophosphorus compound with the formula CHPCl. This colourless viscous liquid is commonly used in the synthesis of phosphine ligands.
Allotropes of phosphorus
Elemental phosphorus can exist in several allotropes, the most common of which are white and red solids. Solid violet and black allotropes are also known. Gaseous phosphorus exists as diphosphorus and atomic phosphorus.
Monocrotophos
Monocrotophos is an organophosphate insecticide. It is acutely toxic to birds and humans, so it has been banned in the U.S., the E.U. and many other countries, however it is still available in India.
Organophosphate
The phosphate esters bearing OH groups are acidic and partially deprotonated in aqueous solution. For example, DNA and RNA are polymers of the type Polyphosphates also form esters; an important example of an ester of a polyphosphate is ATP, which is the monoester of triphosphoric acid (HPO).
Organophosphate
For instance, parathion, one of the first OPPs commercialized, is many times more potent than malathion, an insecticide used in combating the Mediterranean fruit fly (Med-fly) and West Nile Virus-transmitting mosquitoes. Human and animal exposure to them can be through ingestion of foods containing them, or via absorption through the skin or lungs.
Organophosphate poisoning
A number of measurements exist to assess exposure and early biological effects for organophosphate poisoning. Measurements of OP metabolites in both the blood and urine can be used to determine if a person has been exposed to organophosphates. Specifically in the blood, metabolites of cholinesterases, such as butyrylcholinesterase (BuChE) activity in plasma, neuropathy target esterase (NTE) in lymphocytes, and of acetylcholinesterase (AChE) activity in red blood cells. Due to both AChE and BuChE being the main targets of organophosphates, their measurement is widely used as an indication of an exposure to an OP. The main restriction on this type of diagnosis is that depending on the OP the degree to which either AChE or BuChE are inhibited differs; therefore, measure of metabolites in blood and urine do not specify for a certain OP. However, for fast initial screening, determining AChE and BuChE activity in the blood are the most widely used procedures for confirming a diagnosis of OP poisoning. The most widely used portable testing device is the Test-mate ChE field test, which can be used to determine levels of Red Blood Cells (RBC), AChE and plasma (pseudo) cholinesterase (PChE) in the blood in about four minutes. This test has been shown to be just as effective as a regular laboratory test and because of this, the portable ChE field test is frequently used by people who work with pesticides on a daily basis.
Diethylphosphite
Diethylphosphite is the organophosphorus compound with the formula (CHO)P(O)H. It is a popular reagent for generating other organophosphorus compounds, exploiting the high reactivity of the P-H bond. Diethylphosphite is a colorless liquid. The molecule is tetrahedral.
Acephate
It is considered non-phytotoxic on many crop plants. Acephate and its primary metabolite, methamidophos, are toxic to Heliothis spp. that are considered resistant to other organophosphate insecticides. Acephate emits toxic fumes of various oxides of phosphorus, nitrogen, and sulfur when heated to decomposition. Symptoms of exposure to acephate include a slight irritation of eyes and skin.
Organophosphorus compound
Phosphine oxides (designation σλ) have the general structure RP=O with formal oxidation state V. Phosphine oxides form hydrogen bonds and some are therefore soluble in water. The P=O bond is very polar with a dipole moment of 4.51 D for triphenylphosphine oxide.
Tris(1,3-dichloro-2-propyl)phosphate
Tris(1,3-dichloroisopropyl)phosphate (TDCPP) is a chlorinated organophosphate. Organophosphate chemicals have a wide variety of applications and are used as flame retardants, pesticides, plasticizers, and nerve gases. TDCPP is structurally similar to several other organophosphate flame retardants, such as tris(2-chloroethyl) phosphate (TCEP) and tris(chloropropyl)phosphate (TCPP). TDCPP and these other chlorinated organophosphate flame retardants are all sometimes referred to as "chlorinated tris".
Bicyclic phosphate
Bicyclic phosphate is a class of bicyclic organophosphate compound that are used as flame retardants, stabilizers and antioxidants. They are also used in spectroscopic studies.
Disodium hydrogen phosphite
Disodium hydrogen phosphite is the name for inorganic compounds with the formula NaHPO(H2O). The commonly encountered salt is the pentahydrate. A derivative of phosphorous acid (HP(O)(OH)), it contains the anion HPO. Its common name suggests that it contains an acidic hydrogen atom, as in sodium hydrogen carbonate. However, this name is misleading as the hydrogen atom is not acidic, being bonded to phosphorus rather than oxygen. The salt has reducing properties. It is white or colorless solid, and is little studied.
Phosphine oxide
Phosphine oxides are phosphorus compounds with the formula OPX. When X = alkyl or aryl, these are organophosphine oxides. Triphenylphosphine oxide is an example. An inorganic phosphine oxide is phosphoryl chloride (POCl). Such compounds are thermally stable, decomposing only above 450 °C. Phosphoryl refers to a functional group drawn with a phosphorus-oxygen double bond.
Organosulfate
Organosulfates are a class of organic compounds sharing a common functional group commonly with the structure R-O-SO. The SO core is a sulfate group and the R group is any organic residue. All organosulfates are formally esters derived from alcohols and sulfuric acid, although many are not prepared in this way. Many sulfate esters are used in detergents, and some are useful reagents. Alkyl sulfates consist of a hydrophobic hydrocarbon chain, a polar sulfate group (containing an anion) and either a cation or amine to neutralize the sulfate group. Examples include: sodium lauryl sulfate (also known as sulfuric acid mono dodecyl ester sodium salt) and related potassium and ammonium salts.
Pesticide
Organophosphate and carbamate insecticides have a similar mode of action. They affect the nervous system of target pests (and non-target organisms) by disrupting acetylcholinesterase activity, the enzyme that regulates acetylcholine, at nerve synapses. This inhibition causes an increase in synaptic acetylcholine and over-stimulation of the parasympathetic nervous system. Many of these insecticides, first developed in the mid 20th century, are very poisonous. Although commonly used in the past, many older chemicals have been removed from the market due to their health and environmental effects ("e.g." DDT, chlordane, and toxaphene). However, many organophosphates are not persistent in the environment.
Organophosphorus acid anhydrolase
Organophosphorus acid anhydrolase (OPAA) is an enzyme that been shown to be particularly effective in detoxifying organophosphorus-containing compounds, such as deadly nerve gas used in chemical warfare. The enzyme is found in a diverse range of organisms, including protozoa, squid and clams, mammals, and soil bacteria. A highly active form of the enzyme is typically isolated from the marine bacteria "Alteromonas undina" for laboratory study. This form is both halophilic and thermophilic, making it particularly useful for detoxification applications. A slightly less active variant of OPAA has also been isolated in mung beans and slime mold duckweed.
Nickel phosphate
Nickel phosphate is an inorganic compound with the formula Ni(PO). Its octahydrate Ni(PO)·8(HO) is a light green solid that occurs as the mineral arupite.
Organophosphorus compound
The parent phosphorane (σλ) is PH, which is unknown. Related compounds containing both halide and organic substituents on phosphorus are fairly common. Those with five organic substituents are rare, although P(CH) is known, being derived from P(CH) by reaction with phenyllithium.
Phosphide
Many organophosphides are known. Common examples have the formular RPM where R is an organic substituent and M is a metal. One example is lithium diphenylphosphide. The Zintl cluster is obtained with diverse alkali metal derivatives.
Organophosphate
Anatoxin-a(S) is a naturally occurring organophosphate produced by cyanobacteria.
Exopolyphosphatase
PPX was discovered by the lab of Nobel laureate Arthur Kornberg in 1993 and is part of the polyphosphate operon along with polyphosphate kinase, the enzyme which synthesizes polyphosphate. The Kornberg lab was very interested in polyphosphate and published a series of papers elucidating the metabolism and roles of polyphosphate "in vivo". Their interest in polyphosphate led them to identify and characterize the polyphosphate operon (which includes polyphosphate kinase [PPK] and PPX) and develop a wide variety of assays and techniques for quantification of polyphosphate production and degradation, "in vitro" and "in vivo". The results of these studies of polyphosphate by the Kornberg lab led Kornberg to speculate that due to its high energy and phosphate content and the degree to which it is conserved across species, polyphosphate may have been the precursor to RNA, DNA, and proteins.
Sulfotep
Sulfotep (O,O,O',O'-Tetraethyldithiopyrophosphate) is a pesticide commonly used in greenhouses as a fumigative agent. The substance is also known as TEDP, Dithione, Dithiophos and many others. Sulfotep belongs to the class of chemicals named organophosphates. It has a cholinergic effect, involving depression of the cholinesterase activity of the peripheral and central nervous system. The transduction of signals is disturbed at the synapses that make use of acetylcholine. This is the same mechanism of action as nerve agents such as VX, although sulfotep is significantly less potent.
Organophosphate poisoning
Organophosphates inhibit AChE, causing OP poisoning by phosphorylating the serine hydroxyl residue on AChE, which inactivates AChE. AChE is critical for nerve function, so the irreversible blockage of this enzyme, which causes acetylcholine accumulation, results in muscle overstimulation. This causes disturbances across the cholinergic synapses and can only be reactivated very slowly, if at all. Paraoxonase (PON1) is a key enzyme involved in OP pesticides and has been found to be critical in determining an organism's sensitivity to OP exposure.
Kabachnik–Fields reaction
In organophosphorus chemistry, the Kabachnik–Fields reaction is a three-component organic reaction forming α-aminomethylphosphonates from an amine, a carbonyl compound, and a dialkyl phosphonate, (RO)P(O)H (that are also called dialkylphosphites). Aminophosphonates are synthetic targets of some importance as phosphorus analogues of α-amino acids (a bioisostere). This multicomponent reaction was independently discovered by Martin Izrailevich Kabachnik and Ellis K. Fields in 1952. The reaction is very similar to the two-component Pudovik reaction, which involves condensation of the phosphite and a preformed imine.
Organothiophosphate
Generally these compounds feature tetrahedral phosphorus(V) centers. Classically, thiophosphates would include a P=S double bond as illustrated by Malathion. The terminology is used loosely and thiophosphates include P-S single bonds as illustrated by the drug Amifostine.
Acephate
Acephate is an organophosphate foliar and soil insecticide of moderate persistence with residual systemic activity of about 10–15 days at the recommended use rate. It is used primarily for control of aphids, including resistant species, in vegetables (e.g. potatoes, carrots, greenhouse tomatoes, and lettuce) and in horticulture (e.g. on roses and greenhouse ornamentals). It also controls leaf miners, caterpillars, sawflies, thrips, and spider mites in the previously stated crops as well as turf, and forestry. By direct application to mounds, it is effective in destroying imported fire ants.
Phosmet
Phosmet is an organophosphate, consisting of a phthalimide and a dithiophosphate ester, with two methyl groups. The structure is a benzene ring connected to an imide, which is connected to the dithiophosphate.
Organophosphate
As of 2013, thirty-six types of organophosphates were registered for use in the United States. Organophosphates are currently used in a variety of environments (e.g. agriculture, gardens and veterinary practices), however, several notable OPs have been discontinued for use. This includes parathion, which is no longer registered for any use, and chlorpyrifos (as mentioned previously), which is no longer registered for home use. And again, other than for agricultural use, the OP diazinon has been banned in the U.S.
Diphosphines
Diphosphines, sometimes called bisphosphanes, are organophosphorus compounds most commonly used as bidentate phosphine ligands in inorganic and organometallic chemistry. They are identified by the presence of two phosphino groups linked by a backbone, and are usually chelating. A wide variety of diphosphines have been synthesized with different linkers and R-groups. Alteration of the linker and R-groups alters the electronic and steric properties of the ligands which can result in different coordination geometries and catalytic behavior in homogeneous catalysts.
Paraoxonase
Paraoxonases are a family of mammalian enzymes with aryldialkylphosphatase activity. There are three paraoxonase isozymes, which were originally discovered for their involvement in the hydrolysis of organophosphates.
Organophosphate
Organophosphites can be readily oxidised to give organophosphates
Organophosphorus compound
Organophosphorus chemistry is the corresponding science of the properties and reactivity of organophosphorus compounds. Phosphorus, like nitrogen, is in group 15 of the periodic table, and thus phosphorus compounds and nitrogen compounds have many similar properties. The definition of organophosphorus compounds is variable, which can lead to confusion. In industrial and environmental chemistry, an organophosphorus compound need contain only an organic substituent, but need not have a direct phosphorus-carbon (P-C) bond. Thus a large proportion of pesticides (e.g., malathion), are often included in this class of compounds.
Phorate
Phorate is an organophosphate used as an insecticide and acaricide.
Phosphite ester
In chemistry a phosphite ester or organophosphite usually refers to an organophosphorous compound with the formula P(OR). They can be considered as esters of an unobserved tautomer phosphorous acid, HPO, with the simplest example being trimethylphosphite, P(OCH). Some phosphites can be considered esters of the dominant tautomer of phosphorous acid (HP(O)(OH)). The simplest representative is dimethylphosphite with the formula HP(O)(OCH). Both classes of phosphites are usually colorless liquids.
Organophosphorus compound
The parent compound of the phosphines is PH, called phosphine in the US and British Commonwealth, but phosphane elsewhere. Replacement of one or more hydrogen centers by an organic substituents (alkyl, aryl), gives PHR, an organophosphine, generally referred to as phosphines.
Phosphate
In biological systems, phosphorus is found as a free phosphate ion in solution and is called inorganic phosphate, to distinguish it from phosphates bound in various phosphate esters. Inorganic phosphate is generally denoted P and at physiological (homeostatic) pH primarily consists of a mixture of and ions.
Phosphite anion
Organic esters of hydrogen phosphites are anions with the formula HP(O)OR (R = organic group). One commercial example is the fungicide fosetyl-Al with the formula [CHOP(H)O]Al.
Monofluorophosphate
Organic derivatives can be highly toxic and include diisopropyl fluorophosphate. Some of the Novichok agents are monofluorophosphate esters. Names are given to these by naming the groups attached as esters and then adding "fluorophosphonate" to the end of the name. Two organic groups can be attached. Other related nerve gas substances may not be esters, and instead have carbon-phosphorus or nitrogen-phosphorus bonds. The organic fluorophosphonates react with serine esterases and serine proteases irreversibly. This prevents these enzymes from functioning. Such an important enzyme is acetylcholinesterase as found in most animals. Some of the organic esters are detoxified in mammals by an enzym in the blood and liver called paraoxonase PON1.
Phosphoramidate
Phosphoramidates (sometimes also called amidophosphates) are a class of phosphorus compounds structurally related to phosphates (or organophosphates) via the substitution of an OR for a NR. They are derivatives of phosphoramidic acids P(=O)(OH)(NR), P(=O)(OH)(NR).
Aryldialkylphosphatase
Organophosphates are not toxic to bacteria, but they act as acetylcholinesterase inhibitors in animals. Some species of bacteria are also able to utilize organophosphates as a nutrient and carbon source.
Pyrophosphate
In chemistry, a pyrophosphate is a phosphorus oxyanion. Compounds such as salts and esters are also called pyrophosphates. The group is also called diphosphate or dipolyphosphate, although this should not be confused with phosphates. As a food additive, diphosphates are known as E450. A number of hydrogen pyrophosphates also exist, such as NaHPO, as well as the normal pyrophosphates.
Triphos
Triphos is the name for certain organophosphorus ligands. They are air-sensitive white solids that function as tridentate ligands in coordination and organometallic chemistry.
Organophosphorus compound
Organophosphines are nucleophiles and ligands. Two major applications are as reagents in the Wittig reaction and as supporting phosphine ligands in homogeneous catalysis.
Phosphate
In ecological terms, because of its important role in biological systems, phosphate is a highly sought after resource. Once used, it is often a limiting nutrient in environments, and its availability may govern the rate of growth of organisms. This is generally true of freshwater environments, whereas nitrogen is more often the limiting nutrient in marine (seawater) environments. Addition of high levels of phosphate to environments and to micro-environments in which it is typically rare can have significant ecological consequences. For example, blooms in the populations of some organisms at the expense of others, and the collapse of populations deprived of resources such as oxygen (see eutrophication) can occur. In the context of pollution, phosphates are one component of total dissolved solids, a major indicator of water quality, but not all phosphorus is in a molecular form that algae can break down and consume.
Organophosphate
An organic diet is an effective way to reduce exposure to the organophosphorus pesticides commonly used in agricultural production. Organophosphate metabolite levels rapidly drop, and for some metabolites, become undetectable in children's urine when an organic diet is consumed. This is speculative based on a short study of 23 children, in which only a few organophosphate compounds were potentially reduced, no effect was shown for the majority of them that were found in the samples.
Organophosphorus compound
Phosphonates are esters of phosphonic acid and have the general formula RP(=O)(OR'). Phosphonates have many technical applications, a well-known member being glyphosate, better known as Roundup. With the formula (HO)P(O)CHNHCHCOH, this derivative of glycine is one of the most widely used herbicides. Bisphosphonates are a class of drugs to treat osteoporosis. The nerve gas agent sarin, containing both C–P and F–P bonds, is a phosphonate.
Phosphite anion
A phosphite anion or phosphite in inorganic chemistry usually refers to [HPO] but includes [HPO] ([HPO(OH)]). These anions are the conjugate bases of phosphorous acid (HPO). The corresponding salts, e.g. sodium phosphite (NaHPO) are reducing in character.
Organophosphate poisoning
Organophosphate poisoning is poisoning due to organophosphates (OPs). Organophosphates are used as insecticides, medications, and nerve agents. Symptoms include increased saliva and tear production, diarrhea, vomiting, small pupils, sweating, muscle tremors, and confusion. While onset of symptoms is often within minutes to hours, some symptoms can take weeks to appear. Symptoms can last for days to weeks.
Organophosphate poisoning occurs most commonly as a suicide attempt in farming areas of the developing world and less commonly by accident. Exposure can be from drinking, breathing in the vapors, or skin exposure. The underlying mechanism involves the inhibition of acetylcholinesterase (AChE), leading to the buildup of acetylcholine (ACh) in the body. Diagnosis is typically based on the symptoms and can be confirmed by measuring butyrylcholinesterase activity in the blood. Carbamate poisoning can present similarly.
Prevention includes banning very toxic types of organophosphates. Among those who work with pesticides the use of protective clothing and showering before going home is also useful. In those who have organophosphate poisoning the primary treatments are atropine, oximes such as pralidoxime, and diazepam. General measures such as oxygen and intravenous fluids are also recommended. Attempts to decontaminate the stomach, with activated charcoal or other means, has not been shown to be useful. While there is a theoretical risk of health care workers taking care of a poisoned person becoming poisoned themselves, the degree of risk appears to be very small.
OPs are one of the most common causes of poisoning worldwide. There are nearly 3 million poisonings per year resulting in two hundred thousand deaths. Around 15% of people who are poisoned die as a result. Organophosphate poisoning has been reported at least since 1962.
Dimethoate
Dimethoate is a widely used organophosphate insecticide and acaricide. It was patented and introduced in the 1950s by American Cyanamid. Like other organophosphates, dimethoate is an acetylcholinesterase inhibitor which disables cholinesterase, an enzyme essential for central nervous system function. It acts both by contact and through ingestion. It is readily absorbed and distributed throughout plant tissues, and is degraded relatively rapidly.
Organophosphate poisoning
Organophosphate pesticides are one of the top causes of poisoning worldwide, with an annual incidence of poisonings among agricultural workers varying from 3-10% per country.
Dichlofenthion
Dichlofenthion is generally considered to be an organophosphate pesticide, although in a strict chemical sense, it is a phosphorothioate. Because most organophosphate pesticides biodegrade relatively quickly, they are generally regarded as safe for use. While this may be true for most compounds, bacteria still require time to adapt to break down new compounds introduced to the soil. It has been shown that degradation rates increase as the same compounds are introduced repeatedly into the soil.
Phosphite anion
In contrast to the paucity of evidence for , the corresponding arsenic ion, ortho-arsenite, is known. An example is AgAsO as well as the polymeric meta-arsenite . The iso-electronic sulfite ion, is known from its salts.
Inorganic phosphites (containing ) have been applied to crops to combat fungus-like pathogens of the order Oomycetes. The situation is confusing because of the similarity in name between phosphite and phosphate (a major plant nutrient and fertilizer ingredient), and controversial because phosphites have sometimes been advertised as fertilizers, even though they are converted to phosphate too slowly to serve as a plant's main phosphorus source. Lemoynie and others have described this complicated situation and noted that calling phosphites fertilizers avoided the regulatory complication and negative public perceptions that might have been incurred by registering them as fungicides.
Organophosphorus compound
Intermediate between phosphites and phosphines are phosphonites (P(OR)R') and phosphinite (P(OR)R'). Such species arise via alcoholysis reactions of the corresponding phosphinous and phosphonous chlorides ((PClR') and PClR', respectively).
Phosphate
The phosphate ion is a polyatomic ion with the empirical formula and a molar mass of 94.97 g/mol. It consists of one central phosphorus atom surrounded by four oxygen atoms in a tetrahedral arrangement. The phosphate ion carries a −3 formal charge and is the conjugate base of the hydrogen phosphate ion, , which is the conjugate base of , the dihydrogen phosphate ion, which in turn is the conjugate base of , phosphoric acid. A phosphate salt forms when a positively charged ion attaches to the negatively charged oxygen atoms of the ion, forming an ionic compound.
Neutral cholesterol ester hydrolase 1
NCEH can break down organophosphates like the pesticide metabolite chlorpyrifos oxon. Conversely, enzymatic activity can be inhibited by organophosphates.
Carbophenothion
Carbophenothion is a highly toxic organophosphate insecticide and acaricide. Organophosphates are acetylcholinesterase inhibitors and disrupt the signal transduction at the cholinergic synapse. It is classified as Restricted Use Pesticide (RUP) by the Environmental Protection Agency (EPA). Carbophenothion is used in different brands like Trithion. This pesticide contains 80% carbophenothion as its only active ingredient. Because of the widespread use of those organophosphates in the nineties in the US, it was the most common cause of agricultural poisonings.
Organothiophosphate
Oligonucleotide phosphorothioates (OPS) are modified oligonucleotides where one of the oxygen atoms in the phosphate moiety is replaced by sulfur. These compounds are the basis of antisense therapy, e.g., the drugs fomivirsen (Vitravene), Oblimersen, Alicaforsen, and Mipomersen (Kynamro).
Trimethyl phosphite
Trimethyl phosphite is an organophosphorus compound with the formula P(OCH), often abbreviated P(OMe). This colorless liquid is used as a ligand in organometallic chemistry and as a reagent in organic synthesis. The material also has a highly pungent smell. The molecule features a pyramidal phosphorus(III) center bound to three methoxy groups.
Organophosphate
Many "organophosphates" are potent nerve agents, functioning by inhibiting the action of acetylcholinesterase (AChE) in nerve cells. They are one of the most common causes of poisoning worldwide, and are frequently intentionally used in suicides in agricultural areas. Organophosphosphate pesticides can be absorbed by all routes, including inhalation, ingestion, and dermal absorption. Their inhibitory effects on the acetylcholinesterase enzyme lead to a pathological excess of acetylcholine in the body. Their toxicity is not limited to the acute phase, however, and chronic effects have long been noted. Neurotransmitters such as acetylcholine (which is affected by organophosphate pesticides) are profoundly important in the brain's development, and many organophosphates have neurotoxic effects on developing organisms, even from low levels of exposure. Other organophosphates are not toxic, yet their main metabolites, such as their oxons, are. Treatment includes both a pralidoxime binder and an anticholinergic such as atropine.
Organophosphate
The International Agency for Research on Cancer (IARC), found that some organophosphates may increased cancer risk. Tetrachlorvinphos and parathion were classified as "possibly carcinogenic", whereas malathion and diazinon were classified as probably carcinogenic to humans.
Triphenylphosphine sulfide
Triphenylphosphine sulfide (IUPAC name: triphenyl-"λ"-phosphanethione) is the organophosphorus compound with the formula (CH)PS, usually written PhPS (where Ph = phenyl). It is a colourless solid, which is soluble in a variety of organic solvents.
Organophosphate poisoning
The International Agency for Research on Cancer (IARC), found that organophosphates may possibly increased cancer risk. Tetrachlorvinphos and parathion were classified as "possibly carcinogenic", malathion, and diazinon.
Phospholane
Phospholane is the organophosphorus compound with the formula (CH)PH. This colorless liquid is the parent member of a family of five-membered, saturated rings containing phosphorus. Although phospholane itself is only of minor academic interest, the class of C- and P-substituted phospholanes are valued ligands in asymmetric hydrogenation and related areas of homogeneous catalysis. 
Phospholane is prepared by reduction of 1-chlorophospholane, which in turn is obtained by the reaction of 1-phenylphospholane and phosphorus trichloride.
Organophosphate poisoning
Purdey (1998) suggested that organophosphates, in particular Phosmet, induced the transmissible spongiform encephalopathy epidemic of BSE. A European Union food safety Scientific Steering Committee examined the evidence and did not find a link.
Phosphorus
Compounds with P-C and P-O-C bonds are often classified as organophosphorus compounds. They are widely used commercially. The PCl serves as a source of P in routes to organophosphorus(III) compounds. For example, it is the precursor to triphenylphosphine:
Treatment of phosphorus trihalides with alcohols and phenols gives phosphites, e.g. triphenylphosphite:
Similar reactions occur for phosphorus oxychloride, affording triphenylphosphate:
Tris(1,3-dichloro-2-propyl)phosphate
Organophosphate toxicity is classically associated with acetylcholinesterase inhibition. Acetylcholinesterase is an enzyme responsible for breaking down the neurotransmitter acetylcholine. Many organophosphates, especially those designed to act as nerve agents or pesticides, bind with the active site on acetylcholinesterase, preventing it from breaking down acetylcholine. In rodent studies, TDCPP was found to have very low capacity to inhibit acetylcholinesterase, and it is considered to have low acute toxicity. Animals that were given very high doses (>1 g/kg/day) exhibited clinical signs of organophosphate poisoning, including muscle weakness, loss of coordination, hyperactivity, and death.
Organophosphorus compound
Compounds where phosphorus exists in a formal oxidation state of less than III are uncommon, but examples are known for each class. Organophosphorus(0) species are debatably illustrated by the carbene adducts, [P(NHC)], where NHC is an N-heterocyclic carbene. With the formulae (RP) and (RP), respectively, compounds of phosphorus(I) and (II) are generated by reduction of the related organophosphorus(III) chlorides:
Diphosphenes, with the formula RP, formally contain phosphorus-phosphorus double bonds. These phosphorus(I) species are rare but are stable provided that the organic substituents are large enough to prevent catenation. Many mixed-valence compounds are known, e.g. the cage P(CH).
Phosphonate
Phosphonates are one of the three sources of phosphate intake in biological cells. The other two are inorganic phosphate and organophosphates.