Metrifonate

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Metrifonate
Trichlorfon.PNG
Clinical data
Trade names Chlorophos; Mazoten; Dimetox; Chlorak; Trichlorfon; Bovinox; Dioxaphos (and many others) [1] [2]
Other namesTrichlorphon
AHFS/Drugs.com International Drug Names
ATC code
Pharmacokinetic data
Elimination half-life 3 hours
Identifiers
  • (RS)-Dimethyl (2,2,2-trichloro-1-hydroxyethyl)phosphonate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
CompTox Dashboard (EPA)
ECHA InfoCard 100.000.137 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C4H8Cl3O4P
Molar mass 257.43 g·mol−1
3D model (JSmol)
Chirality Racemic mixture
  • COP(=O)(C(C(Cl)(Cl)Cl)O)OC
  • InChI=1S/C4H8Cl3O4P/c1-10-12(9,11-2)3(8)4(5,6)7/h3,8H,1-2H3 X mark.svgN
  • Key:NFACJZMKEDPNKN-UHFFFAOYSA-N X mark.svgN
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Metrifonate (INN) or trichlorfon (USAN) is an irreversible organophosphate acetylcholinesterase inhibitor. [3] It is a prodrug which is activated non-enzymatically into the active agent dichlorvos.

It is used as an insecticide. According to the US Environmental Protection Agency trichlorfon has been used on golf course turf, home lawns, non-food contact areas of food and meat processing plants, ornamental shrubs and plants, and ornamental and baitfish ponds. Used to control caterpillars, white grubs, mole crickets, cattle lice, sod webworms, leaf miners, stink bugs, flies, ants, cockroaches, earwigs, crickets, diving beetle, water scavenger beetle, water boatman backswimmer, water scorpions, giant water bugs and pillbugs. [4] After reregistration, a number of its uses were voluntarily restricted, and currently, it is used in nonfood areas to control flies, roaches, and ants among other pests. Outdoors it is used on ornamental plants, golf courses, and lawn grass to treat lepidopteran larvae pests, it is also used to treat flies in animal husbandry in areas that are not accessible to animals, it also used to control harvester ants. [5]

It can be used to treat schistosomiasis [6] caused by Schistosoma haematobium , [7] but is no longer commercially available. [8]

It has been proposed for use in treatment of Alzheimer's disease, but use for that purpose is not currently recommended. [9]

Bans and restrictions

In the United States, trichlorfon/metrifonate may only be used on nonfood and nonfeed sites. [10]

Trichlorfon/metrifonate was banned in the EU in 2008 (Regulation (EC) 689/2008) and in Brazil in 2010. [11]

Trichlorfon/metrifonate was banned in Argentina in 2018, [12] noting that trichlorvon converts to dichlorvos by metabolism in plants, as well as by biodegradation of the soil.

Trichlorfon/metrifonate was banned in New Zealand in 2011. [13]

Trichlorfon/metrifonate was banned in India from 2020. [14]

Related Research Articles

<span class="mw-page-title-main">Pesticide</span> Substance used to destroy pests

Pesticides are substances that are used to control pests. They include herbicides, insecticides, nematicides, fungicides, and many others. The most common of these are herbicides, which account for approximately 50% of all pesticide use globally. Most pesticides are used as plant protection products, which in general protect plants from weeds, fungi, or insects. In general, a pesticide is a chemical or biological agent that deters, incapacitates, kills, or otherwise discourages pests. Target pests can include insects, plant pathogens, weeds, molluscs, birds, mammals, fish, nematodes (roundworms), and microbes that destroy property, cause nuisance, or spread disease, or are disease vectors. Along with these benefits, pesticides also have drawbacks, such as potential toxicity to humans and other species.

<span class="mw-page-title-main">Insecticide</span> Pesticide used against insects

Insecticides are pesticides used to kill insects. They include ovicides and larvicides used against insect eggs and larvae, respectively. The major use of insecticides is in agriculture, but they are also used in home and garden settings, industrial buildings, for vector control, and control of insect parasites of animals and humans.

<span class="mw-page-title-main">Integrated pest management</span> Approach for economic control of pests

Integrated pest management (IPM), also known as integrated pest control (IPC) that integrates both chemical and non-chemical practices for economic control of pests. The UN's Food and Agriculture Organization defines IPM as "the careful consideration of all available pest control techniques and subsequent integration of appropriate measures that discourage the development of pest populations and keep pesticides and other interventions to levels that are economically justified and reduce or minimize risks to human health and the environment. IPM emphasizes the growth of a healthy crop with the least possible disruption to agro-ecosystems and encourages natural pest control mechanisms." Entomologists and ecologists have urged the adoption of IPM pest control since the 1970s. IPM is a safer pest control framework than reliance on the use of chemical pesticides, mitigating risks such as: insecticide-induced resurgence, pesticide resistance and (especially food) crop residues.

<span class="mw-page-title-main">Lindane</span> Organochlorine chemical and an isomer of hexachlorocyclohexane

Lindane, also known as gamma-hexachlorocyclohexane (γ-HCH), gammaxene, Gammallin and benzene hexachloride (BHC), is an organochlorine chemical and an isomer of hexachlorocyclohexane that has been used both as an agricultural insecticide and as a pharmaceutical treatment for lice and scabies.

<span class="mw-page-title-main">Malathion</span> Chemical compound

Malathion is an organophosphate insecticide which acts as an acetylcholinesterase inhibitor. In the USSR, it was known as carbophos, in New Zealand and Australia as maldison and in South Africa as mercaptothion.

<span class="mw-page-title-main">Imidacloprid</span> Chemical compound

Imidacloprid is a systemic insecticide belonging to a class of chemicals called the neonicotinoids which act on the central nervous system of insects. The chemical works by interfering with the transmission of stimuli in the insect nervous system. Specifically, it causes a blockage of the nicotinergic neuronal pathway. By blocking nicotinic acetylcholine receptors, imidacloprid prevents acetylcholine from transmitting impulses between nerves, resulting in the insect's paralysis and eventual death. It is effective on contact and via stomach action. Because imidacloprid binds much more strongly to insect neuron receptors than to mammal neuron receptors, this insecticide is more toxic to insects than to mammals.

Pesticides vary in their effects on bees. Contact pesticides are usually sprayed on plants and can kill bees when they crawl over sprayed surfaces of plants or other areas around it. Systemic pesticides, on the other hand, are usually incorporated into the soil or onto seeds and move up into the stem, leaves, nectar, and pollen of plants.

<span class="mw-page-title-main">Atrazine</span> Herbicide

Atrazine is a chlorinated herbicide of the triazine class. It is used to prevent pre-emergence broadleaf weeds in crops such as maize (corn), soybean and sugarcane and on turf, such as golf courses and residential lawns. Atrazine's primary manufacturer is Syngenta and it is one of the most widely used herbicides in the United States, Canadian, and Australian agriculture. Its use was banned in the European Union in 2004, when the EU found groundwater levels exceeding the limits set by regulators, and Syngenta could not show that this could be prevented nor that these levels were safe.

<span class="mw-page-title-main">Captan</span> Chemical compound

Captan is a general use pesticide (GUP) that belongs to the phthalimide class of fungicides. It is a white solid, although commercial samples appear yellow or brownish.

<span class="mw-page-title-main">Fenthion</span> Chemical compound

Fenthion is an organothiophosphate insecticide, avicide, and acaricide. Like most other organophosphates, its mode of action is via cholinesterase inhibition. Due to its relatively low toxicity towards humans and mammals, fenthion is listed as moderately toxic compound in U.S. Environmental Protection Agency and World Health Organization toxicity class.

<span class="mw-page-title-main">Dichlorvos</span> Insect killing chemical, organophosphate

Dichlorvos is an organophosphate widely used as an insecticide to control household pests, in public health, and protecting stored products from insects. The compound has been commercially available since 1961. It has become controversial because of its prevalence in urban waterways and the fact that its toxicity extends well beyond insects. Since 1988, dichlorvos cannot be used as a plant protection product in the EU.

<span class="mw-page-title-main">Inter-Regional Research Project Number 4</span>

Inter-Regional Research Project Number 4 is an agricultural program of the USDA Cooperative State Research, Education, and Extension Service which has been in effect since 1963. IR-4 works in coordination with the Environmental Protection Agency to assist in the collection of residue and efficacy data in support of the registration or reregistration of minor use pesticides and the determination of tolerances for residues of minor use chemicals in or on raw agricultural commodities. IR-4's mission is to facilitate registration of sustainable pest management technology for fruits, vegetables, ornamental plants, and other "minor" crops, i.e. high in value but not widely grown in the United States. While most of the minor uses investigated are small enough that it is not profitable for private business to establish the acceptability of a pesticide for individual specialty crops, collectively the specialty crops covered by the project make up almost half of U.S. agricultural crop production and over $40 billion in sales.

<span class="mw-page-title-main">Phosmet</span> 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.

<span class="mw-page-title-main">Dimethoate</span> Chemical compound

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. One of the breakdown products of dimethoate is omethoate, a potent cholinesterase inhibitor, is ten times more toxic than its parent compound.

Neonicotinoids are a class of neuro-active insecticides chemically similar to nicotine, developed by scientists at Shell and Bayer in the 1980s.

<span class="mw-page-title-main">Clothianidin</span> Chemical compound

Clothianidin is an insecticide developed by Takeda Chemical Industries and Bayer AG. Similar to thiamethoxam and imidacloprid, it is a neonicotinoid. Neonicotinoids are a class of insecticides that are chemically similar to nicotine, which has been used as a pesticide since the late 1700s. Clothianidin and other neonicotinoids act on the central nervous system of insects as an agonist of nAChR, the same receptor as acetylcholine, the neurotransmitter that stimulates and activating post-synaptic acetylcholine receptors but not inhibiting AChE. Clothianidin and other neonicotinoids were developed to last longer than nicotine, which is more toxic and which breaks down too quickly in the environment.

<span class="mw-page-title-main">Pesticides in the United States</span>

Pesticides in the United States are used predominantly by the agricultural sector, but approximately a quarter of them are used in houses, yards, parks, golf courses, and swimming pools.

This is an index of articles relating to pesticides.

<span class="mw-page-title-main">Naled</span> Organophosphate insecticide

Naled (Dibrom) is an organophosphate insecticide. Its chemical name is dimethyl 1,2-dibromo-2,2-dichloroethylphosphate.

<span class="mw-page-title-main">Thiamethoxam</span> Chemical compound

Thiamethoxam is the ISO common name for a mixture of cis-trans isomers used as a systemic insecticide of the neonicotinoid class. It has a broad spectrum of activity against many types of insects and can be used as a seed dressing.

References

  1. "Trichlorfon". Haz-Map. U.S. National Library of Medicine. August 2015. Retrieved 2015-10-13.
  2. "Metrifonate". U.S. National Institute of Standards and Technology. Retrieved 2016-09-04.
  3. "NLH - Neurological Conditions - Metrifonate for Alzheimer's disease". Archived from the original on 2009-07-19.
  4. "Trichlorfon Facts". Pesticides: Reregistration. U.S. Environmental Protection Agency.
  5. "Trichlorfon". R.E.D. Facts. U.S. Environmental Protection Agency.
  6. "Monographs: Pharmaceutical substances: Metrifonate (Metrifonatum)". The International Pharmacopoeia Fourth Edition. WHO. Archived from the original on June 3, 2016. Retrieved 2015-10-20. (dead link 31 January 2019)
  7. "Helminths: Schistosomiasis: Metrifonate". WHO Model Prescribing Information: Drugs Used in Parasitic Diseases - Second Edition. WHO. 1995. Archived from the original on July 15, 2010. Retrieved 2015-10-20.
  8. Ross AG, Bartley PB, Sleigh AC, Olds GR, Li Y, Williams GM, McManus DP (April 2002). "Schistosomiasis" (PDF). The New England Journal of Medicine. 346 (16): 1212–20. doi:10.1056/NEJMra012396. PMID   11961151.
  9. López-Arrieta JM, Schneider L (April 2006). López-Arrieta J (ed.). "Metrifonate for Alzheimer's disease". The Cochrane Database of Systematic Reviews (2): CD003155. doi:10.1002/14651858.CD003155.pub3. PMID   16625573.
  10. "Reregistration Eligibility Decision Trichlorfon" (PDF). Retrieved 2018-08-09.
  11. "Decision Guidance Document Trichlorfon - Rotterdam Convention" (PDF). Retrieved 2018-08-09.
  12. "Argentina bans dichlorvos and trichlorfon" . Retrieved 2018-08-09.
  13. "New Zealand bans trichlorfon" . Retrieved 2018-08-09.
  14. "Banned Pesticides in India". 2018-01-17. Retrieved 2018-08-09.