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Flocoumafen

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Flocoumafen Basic information

Product Name:
Flocoumafen
Synonyms:
  • 2h-1-benzopyran-2-one,4-hydroxy-3-(1,2,3,4-tetrahydro-3-(4-((4-(trifluoromethy
  • 4-hydroxy-3-(1,2,3,4-tetrahydro-3-(4-((4-(trifluoromethyl)phenyl)methoxy)phenyl)-1-naphthalenyl)-2h-1-benzopyran-2-on
  • 4-hydroxy-3-(1,2,3,4-tetrahydro-3-(4-(4-trifluoromethylbenzyloxy)phenyl)-1-n
  • 4-hydroxy-3-[1,2,3,4-tetrahydro-3-[4-[[4-(trifluoromethyl)phenyl]methoxy]phenyl]-1-naphthalenyl]-2H-1-Benzopyran-2-one
  • aphthyl)coumarin
  • 4-hydroxy-3-{1,2,3,4-tetrahydro-3-[4-(4-trifluoromethylbenzyloxy) phenyl] naphthyl} coumarin
  • 2-Hydroxy-3-[3-[4-[[4-(trifluoromethyl)phenyl]methoxy]phenyl]-1,2,3,4-tetrahydronaphthalen-1-yl]chromen-4-one
  • 4-Hydroxy-3-(1,2,3,4-tetrahydro-3-(4-((4-(trifluoromethyl)phenyl)methoxy)phenyl)-1-naphthalenyl)-2H-1-benzopyran-2-one
CAS:
90035-08-8
MF:
C33H25F3O4
MW:
542.54
EINECS:
421-960-0
Product Categories:
  • Aromatics
  • Heterocycles
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • F
  • FA - FLPesticides&Metabolites
  • Pesticides
  • Pesticides&Metabolites
  • Rodenticides
  • Alpha sort
  • E-GAlphabetic
Mol File:
90035-08-8.mol
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Flocoumafen Chemical Properties

Melting point:
181 °C
Boiling point:
672.4±55.0 °C(Predicted)
Density 
1.2 g/cm3
vapor pressure 
1.33 x l0-10 Pa (25 °C)
Flash point:
23 °C
solubility 
Chloroform (Slightly), Methanol (Slightly)
form 
Solid
Water Solubility 
1.1 mg l-1
pka
4.50±1.00(Predicted)
color 
White to off-white
InChIKey
KKBGNYHHEIAGOH-UHFFFAOYSA-N
EPA Substance Registry System
2H-1-Benzopyran-2-one, 4-hydroxy-3-[1,2,3,4-tetrahydro-3-[4-[[4-(trifluoromethyl)phenyl]methoxy]phenyl]-1-naphthalenyl]- (90035-08-8)
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Safety Information

Hazard Codes 
T+,N
Risk Statements 
26/27/28-48/23/24/25-50/53
Safety Statements 
28-36/37/39-45-60-61
RIDADR 
3027
WGK Germany 
3
RTECS 
DJ3100300
HazardClass 
6.1(a)
PackingGroup 
I
Hazardous Substances Data
90035-08-8(Hazardous Substances Data)
Toxicity
LD50 in rats, mice, rabbits (mg/kg): 0.25, 0.8, 0.2 orally (Bowler)

MSDS

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Flocoumafen Usage And Synthesis

Uses

Flocoumafen is used to control rodents around buildings. It also has some use in field and plantation crops including cocoa, cotton, oilpalm, rice and sugar cane.

Uses

Flocoumafen is a second-generation anti-coagulant used as a rodenticide. It has a very high toxicity and is restricted to indoor use and sewers (in the United Kingdom). This restriction is mainly due to the increased risk to non-target species. Studies have shown that rodents resistant to first-generation anti-coagulants can be adequately controlled with flocoumafen. The chemical substance is off-white solid, does not mix well with water (1.1 mg/L), and is sparingly soluble in acetone, ethanol, xylene, and octanol. Flocoumafen is stable to hydrolysis. Because of the acute toxicity of flocoumafen and its intended use as a rodenticide, chronic toxicity studies have not been reported. However, flocoumafen is known to cause adverse health effects and abnormal prothrombin.

Definition

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

in vivo

Flocoumafen (0.02-0.1 mg/kg, once a week for 14 weeks) accumulates residues in the liver of rats and cannot be completely metabolized, showing anticoagulant toxicity at high doses[3].

Animal Model:Male Fischer rats[3]
Dosage:0.02 and 0.1 mg/kg; once a week; for 14 weeks
Administration:Oral
Result:Caused noticeable cell accumulation in the liver, with residuals increasing as the dose rises at low doses, while at high doses, it stabilized after a while. The lethal anticoagulant effected only occurs when the binding sites were saturated.
Showed about 30% of the cumulative dosage disappeared from the feces within 3 days after each administration at low doses,for high doses, this value ranges from 18% after the first dose to 59% after the tenth dose, and anticoagulant toxicity appeared after six weeks.

IC 50

MMP-9; Glucocorticoid Receptor 2

Metabolic pathway

Flocoumafen exists as cis and trans isomers (Scheme 1). The tetralin ring adopts its most stable conformation in each case and the two forms have very similar shapes. Both are active rodenticides. The fate of flocoumafen in soils and plants has not been studied in detail because the compound is usually used as a pelleted bait or in a wax block. This limits its dissipation in the environment. Studies in animals and birds have been conducted as part of the assessment of safety and to investigate mode of action. Metabolism is slow in the rat and rapid in Japanese quail but this difference should be interpreted with care because of the 100-fold difference in dose used (see also Overview).

Degradation

Flocoumafen is a stable compound; no detectable degradation occurs at 50 °C at pH 7-9 over 4 weeks.

Flocoumafen Preparation Products And Raw materials

Raw materials

p-Toluenesulfonic acid4-HydroxycoumarinWarfarin1,2,3,4-Tetrahydronaphthalene1,2,3,4-Tetrahydro-1-naphthol

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