Bromadiolone

Bromadiolone
Names
IUPAC name
3-[3-[4-(4-Bromophenyl)phenyl]-3-hydroxy-1-phenylpropyl]-2-hydroxychromen-4-one
Other names
Broprodifacoum; Bromatrol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.044.718
KEGG
Properties
C30H23BrO4
Molar mass 527.41 g·mol−1
Hazards
Main hazards
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Warning label on a tube of rat poison containing bromadiolone on a dike of the Scheldt river in Steendorp, Belgium

Bromadiolone is a potent anticoagulant rodenticide. It is a second-generation 4-hydroxycoumarin derivative and vitamin K antagonist, often called a "super-warfarin" for its added potency and tendency to accumulate in the liver of the poisoned organism. When first introduced to the UK market in 1980, it was effective against the populations that had become resistant to the first generation anticoagulants.

The product may be used both indoors and outdoors for rats and mice.

It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.[1]

Toxicity

Bromadiolone can be absorbed through the digestive tract, through the lungs, or through skin contact. The pesticide is generally given orally.[2] The substance is a vitamin K antagonist. The lack of vitamin K in the circulatory system reduces blood clotting and will cause death due to internal hemorrhaging.[2]

Poisoning doesn't show up for 24 to 36 hours after poison is eaten and often it may take 2–5 days for the signs to show up.

Following are acute LD50 values for various animals (mammals):[2]

  • rats 1.125 mg/kg b.w.
  • mice 1.75 mg/kg b.w.
  • rabbits 1 mg/kg b.w.
  • dogs > 10 mg/kg b.w. (oral MTD)[3]
  • cats > 25 mg/kg b.w. (oral MTD)[3]

Chemistry

The compound is used as a mixture of four stereoisomers. Its two stereoisomeric centers are at the phenyl- and the hydroxyl-substituted carbons in the carbon chain of the substituent at the 3 position of the coumarin.

Bromadiolone

(1R,3S)-isomer

(1S,3R)-isomer

(1R,3R)-isomer

(1S,3S)-isomer

Antidote

Vitamin K1 is used as antidote.[4]

See also

References

  1. ↑ "40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities" (PDF) (July 1, 2008 ed.). Government Printing Office. Retrieved October 29, 2011.
  2. 1 2 3 Bromadiolone Archived December 21, 2006, at the Wayback Machine.
  3. 1 2 The Veterinarian’s Guide to accidental rodenticide ingestion by dogs & cats
  4. ↑ Bromadiolone (Bromone, Maki) Chemical Profile 1/85, Pesticide Management Education Program, Cornell University
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