Structure via PubChem · Public domain (PubChem)
coumaphos
Sign in to saveAlso known as Coumafos, O-(3-chloro-4-methyl-2-oxo-2H-chromen-7-yl) O,O-diethyl thiophosphate, 3-Chloro-4-methyl-7-coumarinyl diethyl phosphorothioate, 3-Chloro-4-methyl-7-hydroxycoumarin diethyl thiophosphoric acid ester, 3-Chloro-7-diethoxyphosphinothioyloxy-4-methylcoumarin, 3-Chloro-7-hydroxy-4-methyl-coumarin O,O-diethyl phosphorothioate, O,O-Diethyl 3-chloro-4-methyl-7-umbelliferone thiophosphate, O,O-Diethyl O-(3-chloro-4-methyl-2-oxo-2H-1-benzopyran-7-yl)phosphorothioate
Coumaphos is a nonvolatile, fat-soluble phosphorothioate with ectoparasiticide properties: it kills insects and mites. It is well known by a variety of brand names as a dip or wash, used on farm and domestic animals to control ticks, mites, flies and fleas.
In the Vinony graph
Within Vinony's link graph, coumaphos is referenced by 394 other articles, and connects out to botulinum toxin group, carbamate and chlorpyrifos.
It is catalogued under topics including Acetylcholinesterase inhibitors, Chembox image size set and Chloroarenes.
Its subject is documented across 13 Wikipedia language editions.
Chemical data
- Formula
- C14H16ClO5PS
- Molecular weight
- 362.8 g/mol
- IUPAC name
- 3-chloro-7-diethoxyphosphinothioyloxy-4-methylchromen-2-one
- SMILES
- CCOP(=S)(OCC)OC1=CC2=C(C=C1)C(=C(C(=O)O2)Cl)C
- InChIKey
- BXNANOICGRISHX-UHFFFAOYSA-N
- XLogP
- 4.5
- Polar surface area
- 86.1 Ų
- H-bond donors
- 0
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
486 papers- Toxicity of Coumaphos Residues in Beeswax Foundation to the Honey Bee Brood.Environmental toxicology and chemistry · 2023
- Coumaphos residue transfer to honey bee brood (Apis mellifera) in realistic scenarios.Research in veterinary science · 2023
- Anthelmintics.Veterinary parasitology · 1993
- Unveiling Molecular Mechanisms Mediating Coumaphos Tolerance in Western Honey Bees (Apis mellifera).Journal of agricultural and food chemistry · 2025
- Simple and Fast Pesticide Nanosensors: Example of Surface Plasmon Resonance Coumaphos Nanosensor.Micromachines · 2023
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 362.014
- Has use
- insecticide
Show 4 more facts
- chemical formula
- C₁₄H₁₆ClO₅PS
- canonical SMILES
- CCOP(=S)(OCC)OC1=CC2=C(C=C1)C(=C(C(=O)O2)Cl)C
- subject has role
- acetylcholinesterase inhibitor
- Commons category
- Coumaphos
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- References
- External links
Coumaphos is a nonvolatile, fat-soluble phosphorothioate with ectoparasiticide properties: it kills insects and mites. It is well known by a variety of brand names as a dip or wash, used on farm and domestic animals to control ticks, mites, flies and fleas.
It is also used to control Varroa mites in honey bee colonies, though in many areas it is falling out of favor as the mites develop resistance and as the residual toxicity effects are becoming better understood.
Excerpted from Wikipedia’s “coumaphos” article, available under the CC BY-SA 4.0 licence.