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 Edit this at Wikidata
KEGG
UNII
  • InChI=1/C30H23BrO4/c31-23-16-14-20(15-17-23)19-10-12-22(13-11-19)26(32)18-25(21-6-2-1-3-7-21)28-29(33)24-8-4-5-9-27(24)35-30(28)34/h1-17,25-26,32-33H,18H2
    Key: OWNRRUFOJXFKCU-UHFFFAOYSA-N
  • Brc1ccc(cc1)c2ccc(cc2)C(O)CC(C\3=C(/O)c4ccccc4OC/3=O)c5ccccc5
Properties
C30H23BrO4
Molar mass 527.414 g·mol−1
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
4
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 rodent populations that had become resistant to 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 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

Paste contains bromadiolone (0.005%)

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 does not show effects for 24 to 36 hours after it is eaten and can take up to 2–5 days to cause death.[clarification needed]

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
(R,S)-Bromadiolon
(1R,3S)-isomer
(S,R)-Bromadiolon
(1S,3R)-isomer
(R,R)-Bromadiolon
(1R,3R)-isomer
(S,S)-Bromadiolon
(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. Archived from the original (PDF) on February 25, 2012. Retrieved October 29, 2011.
  2. ^ a b c Bromadiolone Archived December 21, 2006, at the Wayback Machine
  3. ^ a b "The Veterinarian's Guide to accidental rodenticide ingestion by dogs & cats" (PDF). Archived from the original (PDF) on 2016-07-09. Retrieved 2016-08-03.
  4. ^ "Bromadiolone (Bromone, Maki) Chemical Profile 1/85". Pesticide Management Education Program, Cornell University. Archived from the original on 2019-09-04. Retrieved 2021-05-24.

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