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metrifonate

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EntityQ422991· pop 17· linked from 469 articles

metrifonate

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Also known as Trichlorfon, Chlorophos, 1-Hydroxy-2,2,2-trichloroethylphosphonic acid dimethyl ester, Methyl chlorophos, (±)-Trichlorfon

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

Chemical data

Formula
C4H8Cl3O4P
Molecular weight
257.43 g/mol
IUPAC name
2,2,2-trichloro-1-dimethoxyphosphorylethanol
SMILES
COP(=O)(C(C(Cl)(Cl)Cl)O)OC
InChIKey
NFACJZMKEDPNKN-UHFFFAOYSA-N
XLogP
0.5
Polar surface area
55.8 Ų
H-bond donors
1
H-bond acceptors
4
Formal charge
0

via PubChem

Drug data · ChEMBL

Max clinical phase
Phase 2
Molecule type
Small molecule
Indications
Helminthiasis

via ChEMBL · EBI

Research

1,438 papers

via PubMed

Wikidata facts

Has part
chlorine
Mass
255.923
Show 7 more facts
defined daily dose
40
Commons category
Metrifonate
chemical formula
C₄H₈Cl₃O₄P
canonical SMILES
COP(=O)(C(C(Cl)(Cl)Cl)O)OC
World Health Organisation international non-proprietary name
metrifonate
MCN code
2931.39.14
Sources (3)

via Wikidata · CC0

~2 min read

Encyclopedic overview

2 sections
Contents
  • Bans and restrictions
  • References

Metrifonate (INN) or trichlorfon (USAN) is an irreversible organophosphate acetylcholinesterase inhibitor. 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. 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.

Excerpted from Wikipedia’s “metrifonate” article, available under the CC BY-SA 4.0 licence.