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Brodifacoum

Brodifacoum Structure
Brodifacoum structure
CAS No.
56073-10-0
Chemical Name:
Brodifacoum
Synonyms
bfc;TALON;HAVOC;pp581;volid;KLERAT;pp-581;BROBAIT;ICI 581;Matikus
CBNumber:
CB4682121
Molecular Formula:
C31H23BrO3
Molecular Weight:
523.42
MDL Number:
MFCD00084803
MOL File:
56073-10-0.mol
Last updated:2023-05-15 10:43:24

Brodifacoum 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)
FDA UNII A25P3CP5S7
Pesticides Freedom of Information Act (FOIA) Brodifacoum
EPA Substance Registry System Brodifacoum (56073-10-0)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictogramsGHS hazard pictograms
GHS06,GHS08,GHS09
Signal word  Danger
Hazard statements  H300+H310+H330-H360D-H372-H410
Precautionary statements  P202-P264-P273-P280-P302+P352+P310-P304+P340+P310
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
Toxicity LD50 orally in male, female field rats: 0.16, 0.18 mg/kg (Yuet-Ming)

Brodifacoum Chemical Properties,Uses,Production

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

Rodenticide.

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

Brodifacoum is used to control rodents in and around buildings.

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.

Brodifacoum Preparation Products And Raw materials

Raw materials

4-Hydroxycoumarin 4-Bromobiphenyl Potassium hydroxide Polyphosphoric acid Potassium borohydride
Phenylacetyl chloride Phosphorus tribromide Diethyl malonate 1,2,3,4-Tetrahydro-1-naphthol

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Preparation Products

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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 SOREX BRODIFACOUM RAT TALON(R) NOFAR(R) MOUSE BAIT WEATHERBLOK(R) 2h-1-benzopyran-2-one,3-(3-(4’-bromo(1,1’-biphenyl)-4-yl)-1,2,3,4-tetrahydro-1 3-(3-(4’-bromo-1,1’-biphenyl-4-yl)-1,2,3,4-tetrahydro-1-naphthyl)-4-hydroxyc 3-(3-(4’-bromobiphenyl-4-yl)-1,2,3,4-tetrahydronaphth-1-yl)-4-hydroxycoumari 3-[3-(4’-bromo[1,1’-biphenyl]4-yl)-1,2,3,4-tetrahydro-1-naphthalenyl]-4-hydrox 3-[3-[4’-Bromo[1,1’-biphenyl]-4-yl]-1,2,3,4-tetrahydro-1-naphthalenyl]-4-hydroxy-2H-benzopyran-2-one 4-hydroxy-3-(3-(4’-bromo-4-biphenylyl)-1,2,3,4-tetrahydro-1-naphthyl)coumarin brodifakum bromfenacoum coumarin,3-(3-(4’-bromo-1,1’-biphenyl-4-yl)-1,2,3,4-tetrahydro-1-naphthyl)-4-h -naphthalenyl)-4-hydroxy- pp581 BRODIFACOUM, 50MG, NEAT BRODIFACOUM PESTANAL 100 MG 3-[3-(4'-Bromo[1,1'-biphenyl]-4-yl)-1,2,3,4-tetrahydro-1-naphthalenyl]-4-hydroxy-2H-1-benzopyran-2-one Brodifacoun 2H-1-Benzopyran-2-one, 3-3-(4-bromo1,1-biphenyl-4-yl)-1,2,3,4-tetrahydro-1-naphthalenyl-4-hydroxy- brodifacoum (bsi,iso) 4-hydroxy-3-(3-(4'-bromo-4-biphenylyl)-1,2,3,4-tetrahydro-1-naphthyl)coumarin brodifacoum ICI 581 Matikus 3-[3-（4'-bromobiphen-4-yl)-1,2,3,4-tetrahydro-1-naphthalenyl]-4-hydroxycoumarin 3-[3-[4-(4-Bromophenyl)phenyl]-1,2,3,4-tetrahydronaphthalen-1-yl]-2-hydroxychromen-4-one Brodima Brofenacoum BrodiMat BrodiMax Forte Pasta Klerat Block pp-581 talonrodenticide volid wba8119 y-2h-1-benzopyran-2-one ydroxy- 3-[3-(4-Bromo biphenyl-4)-1,2,3,4-tetrahydrogen naphthyl-1-yl]-4-hydroxy coumarin BRODIFACOUM (TALON RODENTICIDE) Ratak Plus Talon Rat Bait 3-[3-[4-(4-bromophenyl)phenyl]-1,2,3,4-tetrahydronaphthalen-1-yl]-4-hydroxychromen-2-one Broadifacoum (66052-95-7) brodifacoum Brodifacoum (Mixture of Diastereomers) Effectively kill rats / mouse Rodenticide Pellets Brodifacoum 0.005% CAS 56073-10-0 Rat Poison Rodenticide 98%TC Brodifacoum-d4 (Mixture of Diastereomers) Rat Poison Rodenticide