Bromadiolone

Bromadiolone

Names
IUPAC name 3-[3-[4-(4-Bromophenyl)phenyl]-3-hydroxy-1-phenylpropyl]-2-hydroxychromen-4-one
Other names Broprodifacoum; Bromatrol
Identifiers
CAS Number	28772-56-7
ChEMBL	ChEMBL1165553
ChemSpider	10606098
Jmol interactive 3D	Image
KEGG	C18596 Y
PubChem	34322
InChI 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-UHFFFAOYAS
SMILES Brc1ccc(cc1)c2ccc(cc2)C(O)CC(C\3=C(/O)c4ccccc4OC/3=O)c5ccccc5
Properties
Chemical formula	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.

Toxicity

Bromadiolone can be absorbed through the digestive tract, through the lungs, or through skin contact. The pesticide is generally given orally.^[1] 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.^[1]

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):^[1]

• 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)^[2]
• cats > 25 mg/kg b.w. (oral MTD)^[2]

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.

Antidote

Vitamin K1 is used as antidote.^[3]

References