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Cumafuryl (ISO)

Coumafuryl

HCID 54689800
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Grundinformationen

CAS
117-52-2
Standard-SMILES
CC(=O)CC(c1ccco1)c1c(O)c2ccccc2oc1=O
InChIKey
JFIXKFSJCQNGEK-UHFFFAOYSA-N
Summenformel
C17H14O5
Durchschnittliche Molmasse
298,29 g/mol
Monoisotopische Masse
298,08412354

Überblick

Coumafuryl is a hydroxycoumarin.

Namen und Bezeichner

Bevorzugter Name
Coumafuryl
IUPAC
3-[1-(furan-2-yl)-3-oxobutyl]-4-hydroxychromen-2-one
Lokaler Name
Cumafuryl (ISO)
Englischer Name
COUMAFURYL
Summenformel
C17H14O5
Molmasse
298.29

Namen und Synonyme

COUMAFURYL117-52-2RatafinKrumkilTomarinLuratMouse bluesKill-Ko RatCumafurylCaswell No. 0053-(1-Furyl-3-acetylethyl)-4-hydroxycoumarin3-(alpha-Acetonylfurfuryl)-4-hydroxycoumarin
Weitere Namen anzeigen
FumasolKumatoxFUMARINFoumarinFurmarin
7ELL4M4VS8EPA Pesticide Chemical Code 086001BRN 13953424-(2-Furyl)-4-(4-hydroxy-3-coumarinyl)-2-butanone4-(2-Furyl)-4-(4-hydroxy-3-kumarinyl)-2-butanonDTXSID30417982H-1-Benzopyran-2-one, 3-(1-(2-furanyl)-3-oxobutyl)-4-hydroxy-Coumarin, 3-(alpha-acetonylfurfuryl)-4-hydroxy-

Datenbank-Bezeichner

CAS
117-52-2
PubChem CID
54689800
DTXSID
DTXSID3041798
ChEBI
CHEBI:81858
UNII
7ELL4M4VS8
EC Number
204-195-5
Nikkaji
J5.290F

Eigenschaften

Berechnete Struktureigenschaften

XLogP
1,8
Polarare Oberfläche (TPSA)
76,7 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
5
Frei drehbare Bindungen
4
Schwere Atome
22
Formalladung
0
Komplexität
495

Experimentelle und physikochemische Eigenschaften

SpringerMaterials PropertiesFusion temperature
Pesticides · 3 Einträge

Rodenticides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Rodenticides, Anticoagulant

Color/Form · 2 Einträge

White powder

Crystals

Solubility · 2 Einträge

Solubility in water: 150 g/100 ml @ 20 °C /Sodium salt/

Practically insoluble in water; readily soluble in acetone, methyl ethyl ketone, cyclohexanone, ether, dioxane, methylene chloride, dimethylformamide; moderately soluble in toluene, xylene, trichloroethylene, carbon tetrachloride; very slightly soluble in petroleum ether and mineral oils

CorrosivityNon-corrosive
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point124 °C
Vapor PressureVery low at room temperature

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

P260, P264, P270, P273, P301+P316, P319, P321, P330, P405, and P501 (click each P-code to see the statement)

Danger

H301 (97.4%): Toxic if swallowed [Danger Acute toxicity, oral]

P260, P264, P270, P273, P301+P316, P319, P321, P330, P405, and P501 (click each P-code to see the statement)

Gefahrenhinweise

Regulatory Information · 2 Einträge

2004/129/EC

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Hazards SummaryA vitamin K antagonist--causes clotting factor disruption and bleeding; [HSDB] First generation anticoagulant rodenticide; Discontinued by Rhone-Poulenc; [INCHEM] See Warfarin.
FIFRA Requirements · 1 Eintrag

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Fumarin is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA '88. Case No: 0004; Pesticide type: rodenticide; Registration Standard Date: 09/01/1980 PB81-123812; Case Status: No products containing the pesticide are actively registered. Therefore, we are characterizing the case as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): coumafuryl; AI Status: The active ingredient is no longer contained in any registered products ... "cancelled."

Chemie und Industrie

Pharmakologische Informationen

Mechanism of Action · 1 Eintrag

Both 4-hydroxycoumarin derivatives and indandiones (also known as oral anticoagulants) are antagonists of vitamin K. Their use as rodenticides is based on the inhibition of the vitamin K-dependent step in the synthesis of a number of blood coagulation factors. The vitamin K-dependent proteins ...in the coagulation cascade... are the procoagulant factors II (prothrombin), VII (proconvertin), IX (Christmas factor) and X (Stuart-Prower factor), and the coagulation-inhibiting proteins C and S. All these proteins are synthesized in the liver. Before they are released into the circulation the various precursor proteins undergo substantial (intracellular) post-translational modification. Vitamin K functions as a co-enzyme in one of these modifications, namely the carboxylation at well-defined positions of 10-12 glutamate residues into gamma-carboxyglutamate (Gla). The presence of these Gla residues is essential for the procoagulant activity of the various coagulations factors. Vitamin K hydroquinone (KH2) is the active co-enzyme, and its oxidation to vitamin K 2,3-epoxide (KO) provides the energy required for the carboxylation reaction. The epoxide is than recycled in two reduction steps mediated by the enzyme KO reductase... . The latter enzyme is the target enzyme for coumarin anticoagulants. Their blocking of the KO reductase leads to a rapid exhaustion of the supply of KH2, and thus to an effective prevention of the formation of Gla residues. This leads to an accumulation of non-carboxylated coagulation factor precursors in the liver. In some cases these precursors are processed further without being carboxylated, and (depending on the species) may appear in the circulation. At that stage the under-carboxylated proteins are designated as descarboxy coagulation factors. Normal coagulation factors circulate in the form of zymogens, which can only participate in the coagulation cascade after being activated by limited proteolytic degradation. Descarboxy coagulation factors have no procoagulant activity (i.e. they cannot be activated) and neither they can be converted into the active zymogens by vitamin K action. Whereas in anticoagulated humans high levels of circulating descarboxy coagulation factors are detectable, these levels are negligible in warfarin-treated rats and mice. /Anticoagulant rodenticides/

Verwendung und Herstellung

Uses

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Notizen zur Verbindung

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Physical DescriptionWhite solid; [HSDB]
Other Experimental PropertiesVery stable to acids and bases

Physikochemische Eigenschaften

Schmelzpunkt
124 ° · 124°
Siedepunkt
359.71 °C · 359.71°C (rough estimate)
Dichte
1.2006 · 1.2006 (rough estimate)
Brechungsindex
1.62 · 1.6200 (estimate)
Flammpunkt
212 °C · >212 °C
Löslichkeit
Chloroform (Slightly), Methanol (Slightly)
pka
4.5 · 4.50±1.00(Predicted)
Farbe
White
Merck
13 · 13,2582
BRN
6817711 · 6817711
Major Application
agricultureenvironmental
InChI
1S/C17H14O5/c1-10(18)9-12(13-7-4-8-21-13)15-16(19)11-5-2-3-6-14(11)22-17(15)20/h2-8,12,19H,9H2,1H3
InChIKey
JFIXKFSJCQNGEK-UHFFFAOYSA-N
SMILES
CC(=O)CC(c1ccco1)C2=C(O)c3ccccc3OC2=O
EPA chemische Informationen
Coumafuryl (117-52-2)
Hazard Classes and Categories · 3 Einträge

Acute Tox. 3 (97.4%)

Acute toxicity - category 3

Acute Tox. 3 *

Shipment Methods and Regulations · 3 Einträge

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./

The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.

The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

Shipping Name/ Number DOT/UN/NA/IMO · 5 Einträge

UN 3024; Coumarin derivative pesticides, liquid, flammable, toxic, NOS, flashpoint less than 23 °C

UN 3025; Coumarin derivative pesticides, liquid, toxic, flammable, NOS, flashpoint 23 °C or more

UN 3026; Coumarin derivative pesticides, liquid, toxic, NOS

UN 3027; Coumarin derivative pesticides, solid, toxic, NOS

For more Shipping Name/ Number DOT/UN/NA/IMO (Complete) data for COUMAFURYL (6 total), please visit the HSDB record page.

Sicherheit und Schutzausrüstung

Disposal Methods · 1 Eintrag

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

Toxikologische Informationen

Treatment · 1 Eintrag

The primary antidote to fumarin poisoning is immediate administration of vitamin K1 (initially slow intravenous injections of 10-25 mg repeated all 3-6 hours until normalisation of the prothrombin time; then 10 mg orally four times daily as a "maintenance dose"). It is an extremely effective antidote, provided the poisoning is caught before too much damage has been done to the victim's circulatory system. At high doses fumarin can affect the body for many months, and the antidote must be administered regularly for a long period of time. (L1257)

Interactions · 2 Einträge

The following drugs ... may increase ... response to coumarin or indandione derivatives: alcohol (acute intoxication), allopurinol, aminosalicylic acid, amiodarone, anabolic steroids, chloral hydrate, chloramphenicol, cimetidine, clofibrate, co-trimoxazole, danazol, dextrothyroxine sodium, diazoxide, diflunisal, disulfiram, erythromycin, ethacrynic acid, fenoprofen calcium, glucagon, ibuprofen, indomethacin, influenza virus vaccine, isoniazid, meclofenamate, mefenamic acid, methylthiouracil, metronidazole, miconazole, nalidixic acid, neomycin (oral), pentoxifylline, phenylbutazone, propoxyphene, propylthiouracil, quinidine, quinine, salicylates, streptokinase, sulfinpyrazone, sulfonamides, sulindac, tetracyclines, thiazides, thyroid drugs, tricyclic antidepressants, urokinase, vitamin E. /Coumarin & indandione derivatives/

The following drugs ... may ... decrease ... response to coumarin or indandione derivatives: alcohol (chronic alcoholism), barbiturates, carbamazepine, corticosteroids, corticotropin, ethchlorvynol, glutethimide, griseofulvin, mercaptopurine, methaqualone, oral contraceptives containing estrogen, rifampin, spironolactone, vitamin K. /Coumarin & indandione derivatives/

Health EffectsFumarin is an anticoagulant and causes internal bleeding, leading to shock, loss of consciousness, and eventually death. (L1257)
Exposure RoutesOral (ingestion) (L1817) ; dermal (L1817)
Toxicity Summary · 1 Eintrag

Fumarin inhibits the enzyme Vitamin K epoxide reductase. This enzyme is needed for the reconstitution of the vitamin K in its cycle from vitamin K-epoxide, and so fumarin steadily decreases the level of active vitamin K in the blood. Vitamin K is required for the synthesis of important substances including prothrombin, which is involved in blood clotting. This disruption becomes increasingly severe until the blood effectively loses any ability to clot. In addition, fumarin increases permeability of blood capillaries. The blood plasma and blood itself begins to leak from the blood vessels, causing internal bleeding leading to shock, loss of consciousness, and eventually death. (L1257)

Ecotoxicity Excerpts · 4 Einträge

/BIRDS and MAMMALS/ Potential secondary hazards of the anticoagulant rodenticide coumafuryl to birds of prey were examined. Whole rats or mice were killed with each anticoagulant and fed to owls (Bubo virginianus, Aegolius acadicus, Tyto alba). No abnormalities were observed in owls fed rats killed with ... /Coumafuryl/.

/ACCIDENTAL POISONINGS/ Coumafuryl poisoning was observed in young chicks (<1 wk old) with a mortality rate of 100%. Hemorrhage and unclotted blood was noted in the abdominal and thoracic cavities. At necropsy, crops, gizzards contained feed. Analysis of the content detected approximately 340 mg/kg of coumafuryl.

/ACCIDENTAL POISONINGS/ /In domestic animals,/ signs of poisoning occur after a latent period of 12 hr to several days and may include: bruising easily with occasional nose or gum bleeds; blood in stools or urine; excessive bleeding from minor cuts or abrasions; laboured breathing; pale mouth and cold gums; anorexia and general weakness. A reliable indication of an anticoagulant effect is the determination of prothrombin time. /Anticoagulant rodenticides/

/ACCIDENTAL POISONINGS/ Coumafuryl toxicity was diagnosed in chickens <1 week of age. Mortality rate was 100%. Necropsy showed crops and gizzards to be full of feed. There was diffuse hemorrhage and unclotted blood in the abdomen and thorax. Histological examination showed congestion and hemorrhage. The source of the coumafuryl was found to be the wood-straw mats in the chick boxes.

Signs and SymptomsFumarin initially causes dehydration before progressing to bleeding complications. (L1257)
Human Toxicity Excerpts · 1 Eintrag

/HUMAN EXPOSURE STUDIES/ Typical features of poisoning result from increased bleeding tendency and include: minor poisoning: coagulation disturbance detected only by laboratory analyses; moderate poisoning: coagulation disturbance resulting in hematomata, hematuria, blood in feces or excessive bleeding from minor cuts or abrasions, gum bleeding; severe poisoning: retroperitoneal hemorrhage, severe GI bleeding, cerebrovascular accidents, massive hemorrhage (internal bleeding) resulting in shock. If anaemia or liver disease is present then the above features may be more severe and persistent and the poisoning may be more difficult to control. The onset of the signs of poisoning may not be evident until a few days after ingestion. /Anticoagulant rodenticides/

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Populations at Special RiskSRP: Persons with bleeding disorders or who are taking anticoagulants should be protected from exposure.
Antidote and Emergency Treatment · 1 Eintrag

Human exposure to second-generation and indandione anticoagulants produces symptoms consistent with anticoagulation effects (e.g., hematomas, hematemesis, hematuria, easy bruisability). Treatment of cases of exposure, particularly of substantial and repeated exposure, may require vitamin K1 therapy and monitoring of prothrombin times for periods of many months.

Toxicity DataLD50: 14.7 mg/kg (Oral, Mouse) (A584)

Regulatorische Informationen

FIFRA Requirements · 1 Eintrag

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Fumarin is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA '88. Case No: 0004; Pesticide type: rodenticide; Registration Standard Date: 09/01/1980 PB81-123812; Case Status: No products containing the pesticide are actively registered. Therefore, we are characterizing the case as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): coumafuryl; AI Status: The active ingredient is no longer contained in any registered products ... "cancelled."

Sicherheitsdaten

wgk
3
ridadr
3027
RTECS-Nr.
GN4850000
risk_code
25-48/25-52/53
Toxizität
LDLo orl-rat: 400 mg/kg 85GYAZ -,115,71
hazard_code
T
safety_code
37-45-61
hazard_class
6.1(a)
packing_group
II
Speicherklasse
6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Giftige Stoffe Daten
117-52-2(Hazardous Substances Data)
Hazard Classifications
Acute Tox. 2 OralAquatic Chronic 3STOT RE 1 Oral
· 6 Einträge

Used as anticoagulant rodenticide; [HSDB]

Cancelled--no longer registered as a pesticide for use in the US; [HSDB]

Farming (Pesticides) [Category: Industry]

The active ingredient is no longer contained in any registered products ... "cancelled."

Anitcoagulant rodenticide.

For coumafuryl (USEPA/OPP Pesticide Code: 086001) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Methods of ManufacturingPreparation: GB 734142 (1955 to Norddeutsche Affinerie and C. F. Spress & Sohn).
Formulations/Preparations · 2 Einträge

Trade/Other Names: Fumasol, Rat-a-way

Trade Names: Fumarin.

Anwendungen

VerwendenRodenticide.