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Flocoumafen

Flocoumafen
Names
IUPAC name
2-Hydroxy-3-[3-[4-([4-(trifluoromethyl)phenyl]methoxy)phenyl]-1,2,3,4-tetrahydronaphthalen-1-yl] chromen-4-one
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.102.053 Edit this at Wikidata
EC Number
  • 618-367-6
KEGG
UNII
UN number 3027
  • InChI=1S/C33H25F3O4/c34-33(35,36)24-13-9-20(10-14-24)19-39-25-15-11-21(12-16-25)23-17-22-5-1-2-6-26(22)28(18-23)30-31(37)27-7-3-4-8-29(27)40-32(30)38/h1-16,23,28,37H,17-19H2
    Key: KKBGNYHHEIAGOH-UHFFFAOYSA-N
  • O=c1oc2ccccc2c(O)c1C1CC(c2ccc(OCc3ccc(C(F)(F)F)cc3)cc2)Cc2ccccc21
Properties
C33H25F3O4
Molar mass 542.554 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Flocoumafen is a fluorinated, second-generation anticoagulant of the 4-hydroxycoumarin vitamin K antagonist type.[1] It is a second generation (i.e., high potency) chemical in this class, used commercially as a rodenticide. It has a very high toxicity and is restricted to indoor use and sewers (in the UK). This restriction is mainly due to the increased risk to non-target species, especially due to its tendency to bio-accumulate in exposed organisms. Studies have shown that rodents resistant to first-generation anticoagulants can be adequately controlled with flocoumafen.[1] It was synthesized in 1984 by Shell International Chemical.[2]

Toxicity

In most rodents, the LD50 is 1 mg/kg, but it can vary between species: from 0.12 mg/kg in the common vole (Microtus arvalis) to more than 10 mg/kg in the Cairo spiny mouse (Acomys cahirinus). For dogs the LD50 is 0.075-0.25 mg/kg.[2]

Antidote

The antidote to flocoumafen is vitamin K1, which must be administered over a period of several weeks or even months.[3]

References

  1. ^ a b Watt, Barbara E.; Proudfoot, Alex T.; Bradberry, Sally M.; Vale, J Allister (2005). "Anticoagulant Rodenticides". Toxicological Reviews. 24 (4): 259–269. doi:10.2165/00139709-200524040-00005. PMID 16499407.
  2. ^ a b Flocoumafen -- A new anticoagulant rodenticide
  3. ^ "Flocoumafen: Antidote and Emergency Treatment". PubChem.
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