organic chemistry Organic chemistry is a subdiscipline within chemistry involving the science, scientific study of the structure, properties, and reactions of organic compounds and organic matter, organic materials, i.e., matter in its various forms that contain ...

, phosphonates or phosphonic acids are

organophosphorus compound Organophosphorus chemistry is the scientific study of the synthesis and properties of organophosphorus compounds, which are organic compounds containing phosphorus. They are used primarily in pest control as an alternative to chlorinated hydrocarbo ...

s containing groups, where R is an organic group (

alkyl In organic chemistry, an alkyl group is an alkane missing one hydrogen. The term ''alkyl'' is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of . A cycloalkyl group is derived from a cy ...

aryl In organic chemistry, an aryl is any functional group or substituent derived from an aromatic ring, usually an aromatic hydrocarbon, such as phenyl and naphthyl. "Aryl" is used for the sake of abbreviation or generalization, and "Ar" is used ...

). If R is hydrogen then the compound is a dialkyl phosphite, which is a different functional group. Phosphonic acids, typically handled as salts, are generally nonvolatile solids that are poorly

soluble In chemistry, solubility is the ability of a substance, the solute, to form a solution with another substance, the solvent. Insolubility is the opposite property, the inability of the solute to form such a solution. The extent of the solubi ...

organic solvent A solvent (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for p ...

s, but soluble in water and common

alcohol Alcohol may refer to: Common uses * Alcohol (chemistry), a class of compounds * Ethanol, one of several alcohols, commonly known as alcohol in everyday life ** Alcohol (drug), intoxicant found in alcoholic beverages ** Alcoholic beverage, an alco ...

s. Many commercially important compounds are phosphonates, including

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 EPSP inhibitor, inhibiting the plant enzyme 5-en ...

(the active molecule of the herbicide Roundup), and ethephon, a widely used plant growth regulator.

Bisphosphonates Bisphosphonates are a class of drugs that prevent the loss of bone density, used to treat osteoporosis and similar diseases. They are the most commonly prescribed to treat osteoporosis. Evidence shows that they reduce the risk of fracture in p ...

are popular drugs for treatment of

osteoporosis Osteoporosis is a systemic skeletal disorder characterized by low bone mass, micro-architectural deterioration of bone tissue leading to more porous bone, and consequent increase in Bone fracture, fracture risk. It is the most common reason f ...

.Svara, J.; Weferling, N.; Hofmann, T. "Phosphorus Compounds, Organic," in ''Ullmann's Encyclopedia of Industrial Chemistry'', Wiley-VCH, Weinheim, 2008. . In

biochemistry Biochemistry, or biological chemistry, is the study of chemical processes within and relating to living organisms. A sub-discipline of both chemistry and biology, biochemistry may be divided into three fields: structural biology, enzymology, a ...

and

medicinal chemistry Medicinal or pharmaceutical chemistry is a scientific discipline at the intersection of chemistry and pharmacy involved with drug design, designing and developing pharmaceutical medication, drugs. Medicinal chemistry involves the identification, ...

, phosphonate groups are used as stable

bioisostere In medicinal chemistry, bioisosteres are chemical substituents or groups with similar physical or chemical properties which produce broadly similar biological properties in the same chemical compound. In drug design, the purpose of exchanging one b ...

s for phosphate, such as in the antiviral nucleotide analog,

Tenofovir Tenofovir disoproxil, sold under the brand name Viread among others, is a medication used to treat chronic hepatitis B and to prevent and treat HIV/AIDS. It is generally recommended for use with other antiretrovirals. It may be used for pr ...

, one of the cornerstones of anti-

HIV The human immunodeficiency viruses (HIV) are two species of '' Lentivirus'' (a subgroup of retrovirus) that infect humans. Over time, they cause acquired immunodeficiency syndrome (AIDS), a condition in which progressive failure of the im ...

therapy. And there is an indication that phosphonate derivatives are "promising ligands for

nuclear medicine Nuclear medicine (nuclear radiology, nucleology), is a medical specialty involving the application of radioactivity, radioactive substances in the diagnosis and treatment of disease. Nuclear imaging is, in a sense, ''radiology done inside out'', ...

Basic properties

Phosphonates feature tetrahedral phosphorus centers. They are structurally closely related to (and often prepared from)

phosphorous acid Phosphorous acid (or phosphonic acid) is the Compound (chemistry), compound described by the chemical formula, formula . It is diprotic (readily ionizes two protons), not triprotic as might be suggested by its formula. Phosphorous acid is an in ...

.''Modern Phosphonate Chemistry'' by Philippe Savignac and Bogdan Iorga, CRC Press, Boca Raton, FL, 2003. Phosphonic-acid-2D-dimensions-vector

Phosphonate salts are the result of deprotonation of phosphonic acids, which are diprotic acids: :RPO(OH)₂ + NaOH → H₂O + RPO(OH)(ONa) (monosodium phosphonate) :RPO(OH)(ONa) + NaOH → H₂O + RPO(ONa)₂ (disodium phosphonate) Phosphonate esters are the result of condensation of phosphonic acids with alcohols.

Synthesis

Several methods exist for the preparation of phosphonic acids and their salts.

From phosphonic acid

Most processes begin with

(aka phosphonic acid, H₃PO₃), exploiting its reactive P−H bond. Phosphonic acid can be alkylated via the Kabachnik–Fields reaction or Pudovik reaction to give aminophosphonate, which are useful as

chelating Chelation () is a type of bonding of ions and their molecules to metal ions. It involves the formation or presence of two or more separate coordinate bonds between a polydentate (multiple bonded) ligand and a single central metal atom. These l ...

agents. One example is the industrial preparation of nitrilotris(methylenephosphonic acid): :NH₃ + 3 H₃PO₃ + 3 CH₂O → N(CH₂PO₃H₂)₃ + 3 H₂O Phosphonic acid also can be alkylated with

acrylic acid Acrylic acid (IUPAC: prop-2-enoic acid) is an organic compound with the formula CH2=CHCOOH. It is the simplest unsaturated carboxylic acid, consisting of a vinyl group connected directly to a carboxylic acid terminus. This colorless liquid has ...

derivatives to afford carboxyl functionalized phosphonic acids. This reaction is a variant of the

Michael addition In organic chemistry, the Michael reaction or Michael 1,4 addition is a reaction between a Michael donor (an enolate or other nucleophile) and a Michael acceptor (usually an α,β-unsaturated carbonyl) to produce a Michael adduct by creating a c ...

: :CH₂=CHCO₂R + 3 H₃PO₃ → (HO)₂P(O)CH₂CH₂CO₂R In the Hirao coupling dialkyl

phosphite The general structure of a phosphite ester showing the lone pairs on the P In organic chemistry, a phosphite ester or organophosphite usually refers to an organophosphorous compound with the formula P(OR)3. They can be considered as esters of ...

s (which can also be viewed as di-esters of phosphonic acid: (O=PH(OR)₂) undergo a palladium-catalyzed coupling reaction with an

aryl halide In organic chemistry, an aryl halide (also known as a haloarene) is an aromatic compound in which one or more hydrogen atoms directly bonded to an aromatic ring are replaced by a halide ion (such as fluorine F''−'', chlorine Cl−1,−3,−5, br ...

to form a phosphonate.

Michaelis-Arbuzov reaction

Phosphonic esters are prepared using the

Michaelis–Arbuzov reaction The Michaelis–Arbuzov reaction (also called the Arbuzov reaction) is the chemical reaction of a trivalent phosphorus ester with an alkyl halide to form a pentavalent phosphorus species and another alkyl halide. The picture below shows the most c ...

. For example, methyl iodide catalyses the conversion of trimethylphosphite to the phosphonate ester dimethyl methylphosphonate: :P(OMe)₃ → MePO(OMe)₂ These esters can be hydrolysed to the acid (Me = methyl): :MePO(OMe)₂ + H₂O → MePO(OH)₂ + 2 MeOH In the Michaelis–Becker reaction, a hydrogen phosphonate diester is first deprotonated and the resulting anion is alkylated.

From phosphorus trichloride

Vinylphosphonic acid can be prepared by the reaction of PCl₃ and

acetaldehyde Acetaldehyde (IUPAC systematic name ethanal) is an organic compound, organic chemical compound with the chemical formula, formula , sometimes abbreviated as . It is a colorless liquid or gas, boiling near room temperature. It is one of the most ...

: :PCl₃ + CH₃CHO → CH₃CH(O⁻) This adduct reacts with acetic acid: : CH₃CH(O⁻) + 2 CH₃CO₂H → CH₃CH(Cl)PO(OH)₂ + 2 CH₃COCl This chloride undergoes dehydrochlorination to afford the target: :CH₃CH(Cl)PO(OH)₂ → CH₂=CHPO(OH)₂ + HCl In the Kinnear–Perren reaction alkylphosphonyl dichlorides and esters are generated by

alkylation Alkylation is a chemical reaction that entails transfer of an alkyl group. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecting al ...

phosphorus trichloride Phosphorus trichloride is an inorganic compound with the chemical formula PCl3. A colorless liquid when pure, it is an important industrial chemical, being used for the manufacture of phosphites and other organophosphorus compounds. It is toxic ...

in the presence of

aluminium trichloride Aluminium chloride, also known as aluminium trichloride, is an inorganic compound with the formula . It forms a hexahydrate with the formula , containing six water molecules of hydration. Both the anhydrous form and the hexahydrate are col ...

. Alkyltrichlorophosphonium salts are intermediates: :PCl₃ + RCl + AlCl₃ → RPCl + AlCl The RPCl product can then be decomposed with water to produce an alkylphosphonic dichloride RP(=O)Cl₂.

Reactions

Hydrolysis

Phosphonate esters are generally susceptible to hydrolysis under both acidic and basic conditions. Cleavage of the P-C bond is harder but can be achieved under aggressive conditions. :O=PC(OR)₂ + 2 H₂O → O=PC(OH)₂ + 2 ROH

Horner–Wadsworth–Emmons reaction

In the

Horner–Wadsworth–Emmons reaction The Horner–Wadsworth–Emmons (HWE) reaction is a chemical reaction used in organic chemistry of stabilized phosphonate carbanions with aldehydes (or ketones) to produce predominantly E-alkenes. In 1958, Leopold Horner published a modifie ...

dialkyl-phosphonates are deprotonated to give stabilized carbanions, which react with

aldehydes In organic chemistry, an aldehyde () (lat. ''al''cohol ''dehyd''rogenatum, dehydrogenated alcohol) is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred ...

to give E-alkenes with elimination of a dialkyl-

phosphate Phosphates are the naturally occurring form of the element phosphorus. In chemistry, a phosphate is an anion, salt, functional group or ester derived from a phosphoric acid. It most commonly means orthophosphate, a derivative of orthop ...

. :

Structural sub-classes

Bisphosphonates

Compounds containing 2 geminal phosphonate groups are known as

bisphosphonates Bisphosphonates are a class of drugs that prevent the loss of bone density, used to treat osteoporosis and similar diseases. They are the most commonly prescribed to treat osteoporosis. Evidence shows that they reduce the risk of fracture in p ...

. They were first synthesized in 1897 by Von Baeyer and Hofmann and now form the basis for an important class of drugs, used to treat osteoporosis and similar diseases. Examples include HEDP (etidronic acid or Didronel), which is prepared from phosphorous acid and

acetic anhydride Acetic anhydride, or ethanoic anhydride, is the chemical compound with the chemical formula, formula . Commonly abbreviated , it is one the simplest organic acid anhydride, anhydrides of a carboxylic acid and is widely used in the production of c ...

: :2 H₃PO₃ + (CH₃CO)₂O → CH₃C(OH)(PO₃H₂)₂ + CH₃CO₂H

Thiophosphonates

A thiophosphonate group is a functional group related to phosphonate by substitution of an oxygen atom for a sulphur. They are a reactive component of many

pesticide Pesticides are substances that are used to control pests. They include herbicides, insecticides, nematicides, fungicides, and many others (see table). The most common of these are herbicides, which account for approximately 50% of all p ...

s and

nerve agent Nerve agents, sometimes also called nerve gases, are a class of organic chemistry, organic chemicals that disrupt the mechanisms by which nerves transfer messages to organs. The disruption is caused by the blocking of acetylcholinesterase (ACh ...

s. Substituted thiophosphonates can have two main

structural isomer In chemistry, a structural isomer (or constitutional isomer in the IUPAC nomenclature) of a compound is a compound that contains the same number and type of atoms, but with a different connectivity (i.e. arrangement of bonds) between them. The ...

s bonding though either O or S groups to give thione and thiol forms respectively. This is a property they share with related functional groups such as

thiocarboxylic acid In organic chemistry, thiocarboxylic acids or carbothioic acids are organosulfur compounds related to carboxylic acids by replacement of one of the oxygen atoms with a sulfur atom. Two tautomers are possible: a thione form () and a thiol form ( ...

s and

organothiophosphate Organothiophosphates or organophosphorothioates are a subclass of organophosphorus compounds and of thiophosphate compounds. They are the organic compounds that contain a phosphate group in which one or more oxygen atoms is substituted by sulfur. ...

Phosphonamidates

Phosphonamidates are related to phosphonates by substitution of an oxygen atom for a nitrogen. They are a rarely encountered functional group. The nerve agent Tabun is an example.

Occurrence in nature

Phosphonates are one of the three sources of phosphate intake in biological cells. The other two are inorganic phosphate and organophosphates. The naturally occurring phosphonate 2-aminoethylphosphonic acid was first identified in 1959 in plants and many animals, where it is localized in membranes. Phosphonates are quite common among different organisms, from

prokaryote A prokaryote (; less commonly spelled procaryote) is a unicellular organism, single-celled organism whose cell (biology), cell lacks a cell nucleus, nucleus and other membrane-bound organelles. The word ''prokaryote'' comes from the Ancient Gree ...

s to

eubacteria Bacteria (; : bacterium) are ubiquitous, mostly free-living organisms often consisting of one biological cell. They constitute a large domain of prokaryotic microorganisms. Typically a few micrometres in length, bacteria were among the ...

and

mushroom A mushroom or toadstool is the fleshy, spore-bearing Sporocarp (fungi), fruiting body of a fungus, typically produced above ground on soil or another food source. ''Toadstool'' generally refers to a poisonous mushroom. The standard for the n ...

mollusk Mollusca is a phylum of protostomic invertebrate animals, whose members are known as molluscs or mollusks (). Around 76,000 extant species of molluscs are recognized, making it the second-largest animal phylum after Arthropoda. The ...

insect Insects (from Latin ') are Hexapoda, hexapod invertebrates of the class (biology), class Insecta. They are the largest group within the arthropod phylum. Insects have a chitinous exoskeleton, a three-part body (Insect morphology#Head, head, ...

s and others. They were first reported in natural soils by Newman and Tate (1980). The biological role of the natural phosphonates is still poorly understood. Bis- or polyphosphonates have not been found to occur naturally. A number of natural product phosphonate substances with

antibiotic An antibiotic is a type of antimicrobial substance active against bacteria. It is the most important type of antibacterial agent for fighting pathogenic bacteria, bacterial infections, and antibiotic medications are widely used in the therapy ...

properties have been identified. Phosphonate natural product antibiotics include

fosfomycin Fosfomycin, sold under the brand name Monurol among others, is an antibiotic primarily used to treat lower urinary tract infections. It is not indicated for kidney infections. Occasionally it is used for prostate infections. It is generally ...

which is approved by FDA for the treatment of non-complicated

urinary tract infection A urinary tract infection (UTI) is an infection that affects a part of the urinary tract. Lower urinary tract infections may involve the bladder (cystitis) or urethra (urethritis) while upper urinary tract infections affect the kidney (pyel ...

as well as several pre-clinically investigated substances such as Fosmidomycin (inhibitor isoprenyl synthase), SF-2312 (inhibitor of the glycolytic enzyme

enolase Phosphopyruvate hydratase, usually known as enolase, is a metalloenzyme () that catalyses the conversion of 2-phosphoglycerate (2-PG) to phosphoenolpyruvate (PEP), the ninth and penultimate step of glycolysis. The chemical reaction is: :2-ph ...

, and substances of unknown mode of actions such as alahopcin. Although phosphonates are profoundly cell impermeable, natural product phosphonate antibiotics are effective against a number of organisms, because many bacterial species express glycerol-3-phosphate and glucose-6-phosphate importers, which can be hijacked by phosphonate antibiotics. Fosfomycin resistant bacterial strains frequently have mutations that inactivate these transporters; however, such mutations are not maintained in the absence of antibiotic because of the fitness cost they impose.

Uses

In 1998 the consumption of phosphonates was 56,000 tons worldwide – 40,000 tons in the US, 15,000 tons in Europe and less than 800 tons in Japan. The demand of phosphonates grows steadily at 3% annually.

Metal chelants

Since the work of Gerold Schwarzenbach in 1949, phosphonic acids are known as effective

chelating agent Chelation () is a type of bonding of ions and their molecules to metal ions. It involves the formation or presence of two or more separate coordinate bonds between a polydentate (multiple bonded) ligand and a single central metal atom. These l ...

s. The introduction of an

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 ...

group into the molecule to obtain −NH₂−C−PO(OH)₂ increases the metal binding abilities of the phosphonate. Examples for such compounds are NTMP, EDTMP and DTPMP. These phosphonates are the structural analogues to the well-known aminopolycarboxylate such as

EDTA Ethylenediaminetetraacetic acid (EDTA), also called EDTA acid, is an aminopolycarboxylic acid with the formula . This white, slightly water-soluble solid is widely used to bind to iron (Fe2+/Fe3+) and calcium ions (Ca2+), forming water-solubl ...

. The stability of the metal complexes increases with increasing number of phosphonic acid groups. Phosphonates are highly water-soluble while the phosphonic acids are only sparingly so. Phosphonates are effective chelating agents. That is, they bind tightly to di- and trivalent metal ions, which is useful in

water softening Water softening is the removal of calcium, magnesium, and certain other metal cations in hard water. The resulting soft water requires less soap for the same cleaning effort, as soap is not wasted bonding with calcium ions. Soft water also extend ...

. In this way, they prevent formation of insoluble precipitates (scale). The binding of these ligands also suppresses the catalytic properties of metal ions. They are stable under harsh conditions. For these reasons, an important industrial use of phosphonates is in cooling waters, desalination systems, and in oil fields to inhibit scale formation. Phosphonates are also regularly used in reverse osmosis systems as antiscalants. Phosphonates in cooling water systems also serve to control corrosion of iron and steel. In pulp and paper manufacturing and in textile industry they serve as "peroxide bleach stabilizers", by chelating metals that could inactivate the peroxide. In detergents they are used as a combination of chelating agent, scale inhibitor, and bleach stabilizer. Phosphonates are also increasingly used in medicine to treat disorders associated with bone formation and calcium metabolism. Furthermore, they serve as carriers for radionuclides in bone cancer treatments (see samarium-153-ethylene diamine tetramethylene phosphonate).

Concrete admixtures

Phosphonates are also used as concrete retarder. They delay the cement setting time, allowing a longer time to place the concrete or to spread the cement hydration heat on a longer period of time to avoid too high temperature and resulting cracks. They also have favourable dispersing properties and so are investigated as a possible new class of superplasticizers. However, presently, phosphonates are not commercially available as superplasticizers. Superplasticizers are concrete admixtures designed to increase the concrete fluidity and workability of concrete or to decrease its water-to-cement (w/c) ratio. By reducing the water content in concrete, it decreases its porosity, improving so the mechanical properties (compressive and tensile strength) and the durability of concrete (lower water, gas and solutes transport properties).

Warheads in proteomics

Phosphonates and specially diarylphosphonates are also reported to be used as "warhead" or reactive site in proteomics analysis.

Medicine

In medicine, phosphonates and bisphosphonates are commonly used as inhibitors of enzymes which utilize phosphates and diphosphates as substrates. Most notably, these enzymes include those that produce the intermediates of cholesterol biosynthesis. Phosphonate

nucleotide analogue Nucleoside analogues are structural analogues of a nucleoside, which normally contain a nucleobase and a sugar. Nucleotide analogues are analogues of a nucleotide, which normally has one to three phosphates linked to a nucleoside. Both types ...

s such as

tenofovir Tenofovir disoproxil, sold under the brand name Viread among others, is a medication used to treat chronic hepatitis B and to prevent and treat HIV/AIDS. It is generally recommended for use with other antiretrovirals. It may be used for pr ...

cidofovir Cidofovir, brand name Vistide, is a topical or injectable antiviral medication primarily used as a treatment for cytomegalovirus (CMV) retinitis (an infection of the retina of the eye) in people with AIDS. Cidofovir was approved for medical ...

and

adefovir Adefovir is a prescription medicine used to treat (chronic) infections with hepatitis B virus. A prodrug form of adefovir was previously called bis-POM PMEA, with trade names Preveon and Hepsera. It is an orally administered nucleotide analog re ...

are critical antiviral medications, which in various pro-drug forms are used for the treatment of

hepatitis B Hepatitis B is an infectious disease caused by the '' hepatitis B virus'' (HBV) that affects the liver; it is a type of viral hepatitis. It can cause both acute and chronic infection. Many people have no symptoms during an initial infection. ...

and others.

Niche uses

In conjunction with organosilicates, phosphonates are also used to treat "sudden oak death", which is caused by the fungus-like eukaryote ''

Phytophthora ramorum ''Phytophthora ramorum'' is the oomycete known to cause the disease sudden oak death (SOD). The disease kills oak and other species of trees and has had devastating effects on the oak populations in California and Oregon, as well as being present ...

''.

Toxicology

The toxicity of phosphonates to organisms living in water is low. Reported values for 48-hour LC₅₀ values for fish are between 0.1 and 1.1 mM. Also the bioconcentration factor for fish is very low.

Biodegradation

In nature bacteria play a major role in the degradation of phosphonates. Due to the presence of natural phosphonates in the environment, bacteria have evolved the ability to metabolize phosphonates as nutrient sources. Some bacteria use phosphonates as a phosphorus source for growth. Aminophosphonates can also be used as sole nitrogen source by some bacteria. The polyphosphonates used in industry differ greatly from natural phosphonates such as 2-aminoethylphosphonic acid, because they are much larger, carry a high negative charge and are complexed with metals. Biodegradation tests with sludge from municipal sewage treatment plants with HEDP and NTMP showed no indication for any degradation. An investigation of HEDP, NTMP, EDTMP and DTPMP in standard biodegradation tests also failed to identify any biodegradation. It was noted, however, that in some tests due to the high sludge to phosphonate ratio, removal of the test substance from solution observed as loss of DOC was observed. This factor was attributed to adsorption rather than biodegradation. However, bacterial strains capable of degrading aminopolyphosphonates and HEDP under P-limited conditions have been isolated from soils, lakes, wastewater, activated sludge and compost. "No biodegradation of phosphonates during water treatment is observed but

photodegradation Photodegradation is the alteration of materials by light. Commonly, the term is used loosely to refer to the combined action of sunlight and air, which cause oxidation and hydrolysis. Often photodegradation is intentionally avoided, since it dest ...

of the Fe(III)-complexes is rapid. Aminopolyphosphonates are also rapidly oxidized in the presence of Mn(II) and oxygen and stable breakdown products are formed that have been detected in wastewater. The lack of information about phosphonates in the environment is linked to analytical problems of their determination at trace concentrations in natural waters. Phosphonates are present mainly as Ca and Mg-complexes in natural waters and therefore do not affect metal speciation or transport." Phosphonates interact strongly with some surfaces, which results in a significant removal in technical and natural systems.

Phosphonate compounds

Tenofovir alafenamide Tenofovir alafenamide, sold under the brand name Vemlidy, is an antiviral medication used against hepatitis B and HIV. It is used for the treatment of chronic hepatitis B virus (HBV) infection in adults with compensated liver disease an ...

: A pro-drug of the nucleotide analogue

, critical for HIV treatment. *AMPA: Aminomethylphosphonic acid, degradation product of glyphosate * Vinylphosphonic acid: monomer * Dimethyl methylphosphonate (DMMP), one of the simplest phosphonate diesters * Etidronic acid (HEDP): 1-hydroxyethylidene-1,1-diphosphonic acid, used in detergents, water treatment, cosmetics and pharmaceuticals *

ATMP ATMP or aminotris(methylenephosphonic acid) is a phosphonic acid with chemical formula N(CH2PO3H2)3. It is a colorless solid. Its conjugate bases, such as (CH2PO3H)3sup>3-, have chelating properties. ATMP can be synthesized from the Mannich- ...

: Aminotris(methylenephosphonic acid), chelating agent * EDTMP: Ethylenediaminetetra(methylenephosphonic acid), chelating agent *TDTMP: Tetramethylenediaminetetra(methylenephosphonic acid), chelating agent *HDTMP: Hexamethylenediaminetetra(methylenephosphonic acid), chelating agent * DTPMP: Diethylenetriaminepenta(methylenephosphonic acid), chelating agent *PBTC: Phosphonobutanetricarboxylic acid *PMIDA: N-(phosphonomethyl)iminodiacetic acid *CEPA: 2-carboxyethyl phosphonic acid *HPAA: 2-Hydroxyphosphonocarboxylic acid *AMP: Aminotris(methylenephosphonic acid) *BPMG: ''N'',''N''-Bis(phosphonomethyl)glycine *

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 EPSP inhibitor, inhibiting the plant enzyme 5-en ...

: a common agricultural herbicide *

Foscarnet Foscarnet (phosphonomethanoic acid), known by its brand name Foscavir, is an antiviral medication which is primarily used to treat viral infections involving the Herpesviridae family. It is classified as a pyrophosphate Structural analog, analog ...

: for treatment of herpes * Perzinfotel: for treatment of stroke * SF2312: a natural product phosphonate antibiotic inhibitor of

Selfotel Selfotel (CGS-19755) is a drug which acts as a competitive NMDA antagonist, directly competing with glutamate for binding to the receptor. Initial studies showed it to have anticonvulsant, anxiolytic, analgesic and neuroprotective effects, an ...

: an abandoned experimental drug for stroke