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Brodifacoum

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Brodifacoum Basic information

Product Name:
Brodifacoum
Synonyms:
  • KLERAT
  • KLERAT(R)
  • FORWARAT
  • HAVOC
  • BROBAIT
  • BRODIFACOUM
  • 3-(3-(4'-bromo-(1,1'-biphenyl)-4-yl)-1,2,3,4-tetrahydro-1-naphthyl)-4-hydroxy-2h-1-benzopyran-2-one
  • 3-(3-(4'-Bromo-(1,1'-biphenyl)-4-yl)-1,2,3,4-tetrahydro-1-napthalenyl)-4-hydroxycoumarin
CAS:
56073-10-0
MF:
C31H23BrO3
MW:
523.42
EINECS:
259-980-5
Product Categories:
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  • BI - BZPesticides&Metabolites
  • Pesticides
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  • INSECTICIDE
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  • Pesticides&Metabolites
Mol File:
56073-10-0.mol
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Brodifacoum Chemical Properties

Melting point:
228-230°
Boiling point:
679.0±55.0 °C(Predicted)
Density 
1.2940 (rough estimate)
vapor pressure 
41 x l0-6 Pa (20 °C)
refractive index 
1.4620 (estimate)
storage temp. 
0-6°C
solubility 
Chloroform (Slightly), DMSO (Slightly)
pka
5.0 (weak acid, est.)
Water Solubility 
0.24 mg l-1 (20 °C)
Merck 
13,1363
BRN 
8171403
CAS DataBase Reference
56073-10-0(CAS DataBase Reference)
EPA Substance Registry System
Brodifacoum (56073-10-0)
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Safety Information

Hazard Codes 
T+;N,N,T+
Risk Statements 
27/28-48/24/25-50/53
Safety Statements 
1/2-36/37-45-60-61
RIDADR 
UN 2811
WGK Germany 
3
RTECS 
GN4934750
HazardClass 
6.1(a)
PackingGroup 
I
Hazardous Substances Data
56073-10-0(Hazardous Substances Data)
Toxicity
LD50 orally in male, female field rats: 0.16, 0.18 mg/kg (Yuet-Ming)

MSDS

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Brodifacoum Usage And Synthesis

Description

Brodifacoum is a 4-hydroxycoumarin anticoagulant that acts as a vitamin K antagonist. It was registered as a pesticide in 1979 in the United States although in 2008 it was made a restricted use pesticide by the Environmental Protection Agency. This means it can only be used by certified pesticide applicators; however, the makers of D-Con which contains 0.005% brodifacoum by weight have challenged this and brodifacoum is currently available in D-Con and in various other pesticide products for the eradication of mice and rats although it is also used on larger mammals such as possums. Brodifacoum currently remains available to the general public.

Chemical Properties

White Solid

Uses

Brodifacoum is used to control rodents in and around buildings.

Uses

Brodifacoum is a highly lethal vitamin K antagonist anticoagulant poison. In recent years, Broadifacoum, has become one of the world's most widely used pesticides.

Uses

Rodenticide.

Definition

ChEBI: Brodifacoum is a member of benzenes, a ring assembly and a member of naphthalenes.

Hazard

Poison, anticoagulant.

Environmental Fate

Brodifacoum, like other hydroxycoumarins, interferes with the production of vitamin K–dependent coagulation factors. Vitamin K is a cofactor for the carboxylation of specific glutamic acid groups in coagulation factors II (prothrombin), VII, IX, and X. During this step, vitamin K is oxidized to vitamin K 2,3-epoxide. The regeneration of vitamin K by vitamin K 2,3-epoxide reductase is prevented by brodifacoum. As a result, dysfunctional decarboxy-coagulation factors are produced and coagulation is impaired. Brodifacoum is over 100 times more potent than warfarin on a molar basis in rats.

Metabolic pathway

The fate of brodifacoum in soils and plants has not been studied in detail because the compound is usually applied as a pelleted bait or in a wax block. This limits its dissipation in the environment. Studies in animals have been conducted as part of the assessment of safety and to investigate mode of action.

Degradation

Brodifacoum is a stable compound; no detectable degradation occurs at 50 °C or in direct sunlight over 30 days, though it is liable to some photodecomposition in solution.

Toxicity evaluation

Brodifacoum has a very low solubility in water and typically enters water through erosion where it is then found in the sediment. Brodifacoum concentrations are typically not measurable in water systems.
Products that contain brodifacoum as pesticide can remain toxic for a long period of time in the environment. The rate of decay of brodifacoum depends upon the amount of rainfall. As the product that contains brodifacoum degrades over time, the brodifacoum is absorbed into the soil. Soil bacteria degrade brodifacoum over weeks to months although soil type, temperature, and the presence of microorganisms that will degrade brodifacoum all influence the time it takes to degrade.

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