Phosphamidon

Last updated
Phosphamidon
(E,Z)-Phosphamidon Structural Formulae V.1.svg
Names
IUPAC name
(E/Z)-[3-Chloro-4-(diethylamino)-4-oxobut-2-en-2-yl] dimethyl phosphate
Other names
Dimecron
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.032.818 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C10H19ClNO5P/c1-6-12(7-2)10(13)9(11)8(3)17-18(14,15-4)16-5/h6-7H2,1-5H3 X mark.svgN
    Key: RGCLLPNLLBQHPF-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C10H19ClNO5P/c1-6-12(7-2)10(13)9(11)8(3)17-18(14,15-4)16-5/h6-7H2,1-5H3
    Key: RGCLLPNLLBQHPF-UHFFFAOYAA
  • CCN(CC)C(=O)/C(=C(\C)/OP(=O)(OC)OC)/Cl
Properties
C10H19ClNO5P
Molar mass 299.69 g·mol−1
Density 1.2132 g/cm3 [1]
Melting point 120 to 123 °C (248 to 253 °F; 393 to 396 K) [2]
Boiling point 162 °C (324 °F; 435 K)(1.5 mmHg) [3]
Miscible
Hazards
Lethal dose or concentration (LD, LC):
13 mg/kg (mouse, oral) [2]
6 mg/kg (mouse, IV) [2]
20 mg/kg (rat, oral) [2]
26 mg/kg (rat, subcut.) [2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Phosphamidon is an organophosphate insecticide first reported in 1960. [2] [3] It acts as a cholinesterase inhibitor.

The commercial product typically exists as a mixture of 70% (Z)-isomer and 30% (E)-isomer. [1]

Toxicity and regulation

Phosphamidon is very highly toxic to mammals and is listed as WHO Hazard Class Ia. [1] A harvester developed symptoms of moderately severe poisoning after working in a field that had been sprayed with the chemical 2 weeks earlier. He collapsed and exhibited significant depression of serum cholinesterase, but recovered completely within 2 days after successful treatment with atropine. [4] International trade of phosphamidon is covered by the Rotterdam Convention.

Related Research Articles

Cholinesterase Esterase that lyses choline-based esters

In biochemistry, a cholinesterase or choline esterase is a family of esterases that lyses choline-based esters, several of which serve as neurotransmitters. Thus, it is either of two enzymes that catalyze the hydrolysis of these cholinergic neurotransmitters, such as breaking acetylcholine into choline and acetic acid. These reactions are necessary to allow a cholinergic neuron to return to its resting state after activation. For example, in muscle contraction, acetylcholine at a neuromuscular junction triggers a contraction; but for the muscle to relax afterward, rather than remaining locked in a tense state, the acetylcholine must be broken down by a choline esterase. The main type for that purpose is acetylcholinesterase ; it is found mainly in chemical synapses and red blood cell membranes. The other type is butyrylcholinesterase ; it is found mainly in the blood plasma.

Parathion Chemical compound

Parathion, also called parathion-ethyl or diethyl parathion and locally known as "Folidol", is an organophosphate insecticide and acaricide. It was originally developed by IG Farben in the 1940s. It is highly toxic to non-target organisms, including humans, so its use has been banned or restricted in most countries. The basic structure is shared by parathion methyl.

Chlorfenvinphos Chemical compound

Chlorfenvinphos is the common name of an organophosphorus compound that was widely used as an insecticide and an acaricide. The molecule itself can be described as an enol ester derived from dichloroacetophenone and diethylphosphonic acid. Chlorfenvinphos has been included in many products since its first use in 1963. However, because of its toxic effect as a cholinesterase inhibitor it has been banned in several countries, including the United States and the European Union. Its use in the United States was cancelled in 1991.

Organophosphate Class of organophosphorus compounds

Organophosphates are a class of organophosphorus compounds with the general structure O=P(OR)3, a central phosphate molecule with alkyl or aromatic substituents. They can be considered as esters of phosphoric acid. Like most functional groups organophosphates occur in a diverse range of forms, 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 popularity of OPEs as flame retardants came as a substitution for the highly regulated brominated flame retardants. 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. Due to this, OPEs leak into the environment more readily through volatilization, leaching, and abrasion. OPEs have been detected in diverse environmental compartments such as air, dust, water, sediment, soil and biota samples at higher frequency and concentration.

VG (nerve agent) Chemical compound

VG is a "V-series" nerve agent chemically similar to the better-known VX nerve agent. Tetram is the common Russian name for the substance. Amiton was the trade name for the substance when it was marketed as an insecticide by ICI in the mid-1950s.

Demeton-S-methyl is an organic compound with the molecular formula C6H15O3PS2. It was used as an organothiophosphate acaricide and organothiophosphate insecticide. It is flammable. With prolonged storage, Demeton-S-methyl becomes more toxic due to formation of a sulfonium derivative which has greater affinity to the human form of the acetylcholinesterase enzyme, and this may present a hazard in agricultural use.

Aldicarb Chemical compound (insecticide)

Aldicarb is a carbamate insecticide which is the active substance in the pesticide Temik. It is effective against thrips, aphids, spider mites, lygus, fleahoppers, and leafminers, but is primarily used as a nematicide. Aldicarb is a cholinesterase inhibitor which prevents the breakdown of acetylcholine in the synapse. In case of severe poisoning, the victim dies of respiratory failure.

Phosmet Organophosphate non-systemic insecticide

Phosmet is a phthalimide-derived, non-systemic, organophosphate insecticide used on plants and animals. It is mainly used on apple trees for control of codling moth, though it is also used on a wide range of fruit crops, ornamentals, and vines for the control of aphids, suckers, mites, and fruit flies.

Dioxathion Chemical compound

Dioxathion, systematically known as p-dioxane-2,3-diyl ethyl phosphorodithioate, is an organophosphate pesticide. It is used as an insecticide on livestock and as an acaricide on citrus fruits, deciduous fruits and nuts.

Tricresyl phosphate Chemical compound

Tricresyl phosphate (TCP), is a mixture of three isomeric organophosphate compounds most notably used as a fire retardant and in manufacturing for lacquers and varnishes as a plasticizer. Pure tricresyl phosphate is a colorless, viscous liquid, although commercial samples are typically yellow. It is virtually insoluble in water, but easily soluble in organic solvents like toluene, hexane, and diethylether among others. It was synthesized by Alexander Williamson in 1854 upon reacting phosphorus pentachloride with cresol, though today's manufacturers can prepare TCP by mixing cresol with phosphorus oxychloride or phosphoric acid as well. TCP, especially the all-ortho isomer, is the causative agent in a number of acute poisonings. Its chronic toxicity is also of concern. The ortho-isomer is rarely used on its own outside of laboratory studies that require isomeric purity, due to its extremely toxic nature, and is generally excluded from commercial products where TCP is involved.

Demeton Chemical compound

Demeton, sold as an amber oily liquid with a sulphur like odour under the name Systox™, is an organophosphate derivative causing irritability and shortness of breath to individuals repeatedly exposed. It was used as a phosphorothioate insecticide and acaricide and has the chemical formula C8H19O3PS2. Although it was previously used as an insecticide, it is now largely obsolete due to its relatively high toxicity to humans. Demeton consists of two components, demeton-S and demeton-O in a ratio of approximately 2:1 respectively. The chemical structure of demeton is closely related to military nerve agents such as VX and a derivative with one of the ethoxy groups replaced by methyl was investigated by both the US and Soviet chemical-weapons programs under the names V.sub.X and GD-7.

Tetraethyl pyrophosphate Chemical compound

Tetraethyl pyrophosphate, abbreviated TEPP, is an organophosphate compound with the formula [(C2H5O)2P(O)]2O. It is the tetraethyl derivative of pyrophosphate (P2O74-). It is a colorless oil that solidifies near room temperature. It is used as an insecticide. The compound hydrolyzes rapidly.

Cyanophos Chemical compound

Cyanophos is a cholinesterase inhibitor used as an insecticide and avicide; for example, against rice stem borers and house flies. It is part of the chemical class of organophosphorus compounds, and is a yellow to reddish-yellow transparent liquid.

Endothion Chemical compound

Endothion is an organic compound used as an insecticide and acaricides. It is part of the chemical class of organophosphorus compounds. It is generally described as white crystals with a slight odor. It is used as an insecticide, but not sold in the United States or Canada.

Sulfotep Chemical compound

Sulfotep (also known as tetraethyldithiopyrophosphate and TEDP) is a pesticide commonly used in greenhouses as a fumigant. The substance is also known as Dithione, Dithiophos, and many other names. Sulfotep has the molecular formula C8H20O5P2S2 and belongs to the organophosphate class of chemicals. It has a cholinergic effect, involving depression of the cholinesterase activity of the peripheral and central nervous system of insects. The transduction of signals is disturbed at the synapses that make use of acetylcholine. Sulfotep is a mobile oil that is pale yellow-colored and smells like garlic. It is primarily used as an insecticide.

Triazofos Chemical compound

Triazofos is a chemical compound used in acaricides, insecticides, and nematicides.

Tetrachlorvinphos Chemical compound

Tetrachlorvinphos is an organophosphate insecticide used to kill fleas and ticks.

Hexaethyl tetraphosphate Chemical compound

Hexaethyl tetraphosphate (also known as HET) is the organophosphorus compound with the chemical formula [(C2H5O)3P2O3]2O. The compound has not been isolated in pure form but appears to be a colorless liquid at room temperature. Commercial samples appear brown due to impurities. It is a constituent of the insecticide Bladan. In the 1940s, it was about as significant an insecticide as DDT and was referred to as "another of DDT's rivals for fame" in a 1948 book.

IPTBO Chemical compound

IPTBO is a bicyclic phosphate convulsant. It is an extremely potent GABA receptor antagonist that can cause violent convulsions in mice.

Bicyclic phosphate is a class of organophosphate compounds that are used as flame retardants, stabilizers and antioxidants. They are also used in spectroscopic studies.

References

  1. 1 2 3 Data Sheet on Pesticides No. 74: Phosphamidon, International Programme on Chemical Safety
  2. 1 2 3 4 5 6 Jacques, R.; Bein, H. J. (1960). "Toxicology and pharmacology of a new systemic phosphoric acid ester insecticide phosphamidon (2-chloro-2-diethylcarbamoyl-1-methylvinyl dimethyl phosphate)". Archiv für Toxikologie. 18: 316–330. doi:10.1007/BF02226232. S2CID   6714997.
  3. 1 2 Bachmann, Fritz (1960). "Phosphamidon, a new phosphate ester with systemic action". Proc. Intern. Cong. Crop. Protection, 4th Congr., Hamburg. 2: P1153-1155.
  4. S. Gitelson, J. T. Davidson, A. Werczberger. Phosphamidon poisoning. Br. J. Ind. Med. 22: 236-239, 1965.