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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 |  |
| | Flocoumafen Chemical Properties |
| 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 | | Storage Class | 6.1A - Combustible acute toxic Cat. 1 and 2
very toxic hazardous materials | | Hazard Classifications | Acute Tox. 1 Dermal
Acute Tox. 1 Inhalation
Acute Tox. 1 Oral
Aquatic Acute 1
Aquatic Chronic 1
Repr. 1B
STOT RE 1 | | 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) |
| | Flocoumafen Usage And Synthesis |
| Description | Flocoumafen is a coumarin rodenticide defined as a second-generation indirect anticoagulant. It has a low aqueous solubility and a low volatility. Evidence suggests it is persistent in both soil and water systems. Based on physico-chemical properties, there is some risk that the substance may to leach to groundwater. It is moderately toxic to birds and aquatic invertebrates but highly toxic to fish. It has a high mammalian oral toxicity. | | 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. | | 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. | | Definition | ChEBI: Flocoumafen is a ring assembly, a member of naphthalenes and a member of benzenes. | | Production Methods | Flocoumafen is commercially synthesised through a multi-step process involving the construction of its complex coumarin-based structure. The synthesis begins with inexpensive starting materials such as anisole and phenylacetyl chloride, which are sequentially transformed into key intermediates including 4-methoxyphenylacetophenone and 3-(4-methoxyphenyl)-1-tetralone. These intermediates undergo further reactions to form a tetrahydronaphthalene core, which is then coupled with a chromen-4-one moiety to yield the coumarin scaffold. A final etherification step introduces the trifluoromethylbenzyloxy group, completing the flocoumafen molecule. | | Mechanism of action | Flocoumafen is a second generation anticoagulant rodenticide that disrupts the vitamin K cycle, which is essential for the synthesis of blood clotting factors. It acts as a potent antagonist of the enzyme Vitamin K1 epoxide reductase (VKOR), leading to a blockage in the recycling process of Vitamin K. | | 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.
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| | 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. | | Pesticide Type | Rodenticide |
| | Flocoumafen Preparation Products And Raw materials |
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