Name | warfarin |
Synonyms | WARF(R) SAKARAT WARFARIN Warfarat warfarin PROLIN(R) KYPFARIN(R) WARF COMPOUND 42(R) 3-(A-acetonylbenzyl)4-hydroxycoumarin 4-hydroxy-3-(3-oxo-1-phenylbutyl)coumarin DL-3-(ALPHA-ACETONYLBENZYL)-4-HYDROXYCOUMARIN |
CAS | 81-81-2 |
EINECS | 201-377-6 |
InChI | InChI=1/C19H16O4/c1-12(20)11-15(13-7-3-2-4-8-13)17-18(21)14-9-5-6-10-16(14)23-19(17)22/h2-10,15,21H,11H2,1H3 |
Molecular Formula | C19H16O4 |
Molar Mass | 308.33 |
Density | 1.1411 (rough estimate) |
Melting Point | 162-164°C(lit.) |
Boling Point | 356°C |
Flash Point | 2℃ |
Water Solubility | Practically insoluble |
Solubility | Soluble in benzene, 1,4-dioxane (Weast, 1986), and acetone (Sax and Lewis, 1987). Moderatelysoluble in methanol, ethanol, isopropanol, and some oils (Windholz et al., 1983). Also soluble intoluene. |
Vapor Presure | 0.09 at 22 °C (NIOSH, 1997) |
Appearance | Crystalline |
Color | Colorless |
Exposure Limit | NIOSH REL: TWA 0.1 mg/m3, IDLH 100 mg/m3; OSHA PEL: 0.1mg/m3; ACGIH TLV: TWA 0.1 mg/m3. |
Merck | 13,10097 |
BRN | 8868198 |
pKa | pKa 4.90±0.01(H2Ot = 25±0.5I = 0.15 (KCl))(Approximate) |
Storage Condition | 2-8°C |
Refractive Index | 1.4434 (estimate) |
Physical and Chemical Properties |
Colourless, odourless crystals. Soluble in common organic solvents and alkaline media; insoluble in water and hydrocarbon solvents. Used as a rodenticide. UN covers coumarin derived pesticides, solid, toxic. |
Use | Anticoagulant rodenticide, used to kill rats and zokor |
Risk Codes | R61 - May cause harm to the unborn child R48/25 - R52/53 - Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R28 - Very Toxic if swallowed R21 - Harmful in contact with skin R36 - Irritating to the eyes R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R11 - Highly Flammable |
Safety Description | S53 - Avoid exposure - obtain special instructions before use. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. S52 - Not recommended for interior use on large surface areas. S36/37 - Wear suitable protective clothing and gloves. S28 - After contact with skin, wash immediately with plenty of soap-suds. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S16 - Keep away from sources of ignition. |
UN IDs | UN 2811 6.1/PG 1 |
WGK Germany | 3 |
RTECS | GN4550000 |
HS Code | 29322090 |
Hazard Class | 6.1(a) |
Packing Group | I |
Toxicity | EC50 (24-hour) for Daphnia magna 88.8 mg/L (Lilius et al., 1995); acute oral LD50 for rats 186 mg/kg (Hartley and Kidd, 1987), 3 mg/kg (RTECS, 1985) |
warfarin, a highly toxic rodenticide. Rats acute oral LD50 is 3 mg/kg, sensitive to cats, dogs, dogs LD100 20-50mg/kg, cats LD100 5 mg/kg. Low toxicity to cattle, sheep, chicken and duck.
Product use: it is an anti-hemagglutinating rodenticide used to kill rats and zokor.
dosage form: 95% original powder, 2.5% powder, 25% liquid.
characteristics: it is the first generation of anticoagulant rodenticide with low acute toxicity, high chronic toxicity, and multiple times of continuous medication. Good palatability, generally do not produce anti-feeding.
Scope of Application: applicable to the residential area, warehouse, ship, dock, poultry farm and other prevention and control of rats, mice, mice and other rodents.
The racemate is a colorless, odorless, tasteless crystal. Melting point 161 °c. Soluble in acetone, soluble in alcohol, insoluble in benzene and water. The enol form is acidic and forms a salt with a metal. Its sodium salt is soluble in water and insoluble in organic solvents.
4-hydroxycoumarin was synthesized from salicylic acid by esterification with methanol, acylation with acetic anhydride at 40 ℃ and acidification with sodium metal; or by salicylic acid and thionyl chloride by acylation, cyclization, acidification of 4 hydroxy coumarin. In addition, substituted butene-[3]-ketone-[2] was prepared by condensation of benzaldehyde with acetone in the presence of sodium hydroxide. The 4-hydroxy coumarin and substituted butene-[3]-ketone-[2] were refluxed in pyridine, acidified to pH 2 with hydrochloric acid, placed, solidified and recrystallized, the rat-killer.
anticoagulant rodenticide. After the drug into the body of the mice showed anticoagulant effect, so that the mice bleeding and death. Mainly used to kill the mice, rats, rodents and other domestic rodents, can also be used to kill wild rodents.
male rats, female rats, mice, rabbits oral LD50 323mg/kg, 58mg/kg, 374mg/kg, about 800mg/kg; Other reports of male rats, oral LD50:100 in female rats. 3 mg/kg, 8.7 mg/kg. Less toxic to poultry such as chickens, ducks, cattle, sheep, pigs, dogs, cats are more sensitive.
NIST chemical information | information provided by: webbook.nist.gov (external link) |
EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
Introduction | warfarin is an anticoagulant that can only be taken orally, commonly used in storage and prescription of sodium coumarin, more famous brands have Coumadin®. Because of its chemical structure is very similar to vitamin K, it is able to interfere with the operation of blood hormones, reducing the risk of blood clotting in patients. However, because of its strong effect, it is generally only prescribed for patients with high risk of blood coagulation, such as irregular heart rhythm or patients with artificial heart valves. |
pharmacological mechanism | in general, vitamin K is converted into vitamin K(vitamin K epoxide) in the liver, it is then reduced by the "epoxide-reducing enzyme. Warfarin can inhibit the action of this enzyme in the liver, so that prothrombin (prothrombin) lost function, thus preventing blood clotting. |
side effects | oral warfarin commonly known as "thin blood pill", but must pay attention to diet after taking, there are two vitamins that affect the efficacy of the drug, as follows: Vitamin E: enhances the effectiveness of warfarin, easily causing internal bleeding. Vitamin K: will weaken the efficacy of warfarin. |
toxicity | Acute LD503mg/kg (14 mg/kg) in mice, it has also been reported that the acute oral LD50 in mice is 200 mg/kg, the LD100 in dogs is 20-50mg/kg (-300mg/kg), and the LD100 in cats is 5 mg/kg. On the chicken, duck, cattle, sheep less toxic, pigs, dogs, cats more sensitive. |
Use | anticoagulant rodenticide. The mechanism of action is the inhibition of Vitamin K1, which blocks the synthesis of prothrombin in the blood in the liver of the animal. Mainly used in residential areas, grain depots, poultry farms to kill rats. The prepared poison bait was put into the place where the rats were frequently active, and the food was checked every day. Dead rats were found after administration for 3 days, with peak within 1 week. This product is an anticoagulant rodenticide, which is widely used in the world. It is mainly used to kill Mus musculus, Mus musculus, et al, and can also be used to kill wild rodents. The mode of action of the rat is to enter the mouse body after the performance of anti coagulation effect, so that the rat body bleeding and death. In general, the deratization rate can reach more than 90% within three weeks after feeding. The product is also used as an oral anticoagulant. Known as warfarin sodium, for the prevention and treatment of thromboembolic disease. An anticoagulant rodenticide used to kill rats and zokor |
production method | warfarin was prepared by synthesizing benzaldehyde and acetone, and then condensing with 4-hydroxycoumarin. There are 98% raw powder, 2.5% mother powder and 0.025 poison bait. Pure Powder by starch and powder mixed uniformly. The poison bait is made of corn flour and other grains, mixed with the mother powder and the warning color, and then extruded and dried into a strip shape. The wax block poison bait can also be made by mixing the mother powder and paraffin. preparation of 4-hydroxycoumarin with salicylic acid as raw material, first esterification with methanol, and then acylated with acetic anhydride at 40 ℃, and then under the action of metal sodium 240~250 ℃ ring closure, synthesis of 4-hydroxycoumarin by acidification. It can also be prepared by acylation, cyclization and acidification of salicylic acid and thionyl chloride. Preparation of substituted butenes-[3]-ketones-[2]-Benzaldehyde was prepared by condensation of benzaldehyde with acetone in the presence of sodium hydroxide. Synthesis of warfarin the above two intermediates were refluxed in pyridine for 24h to remove pyridine, poured into water, acidified to pH about 2 with hydrochloric acid, placed, solidified, and recrystallized to obtain warfarin. |
category | pesticide |
toxicity grade | highly toxic |
Acute toxicity | oral-rat LD50: 1.6 mg/kg; Oral-mouse LD50: 3 mg/kg |
flammability hazard characteristics | flammable; Highly toxic smoke emitted in fire scene |
storage and transportation characteristics | The warehouse is ventilated and dried at low temperature; It is stored and transported separately from food raw materials |
fire extinguishing agent | Sand, dry powder, foam |
Occupational Standard | TWA 0.1 mg/m3; Tel 0.3 mg/m3 |
toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
immediate life-threatening and health concentration | 100 mg/m3 |
The racemate is a colorless, odorless, tasteless crystal. m.p.159 -161 °c. Soluble in acetone, soluble in alcohol, insoluble in benzene and water. The enol form is acidic and forms a salt with a metal. Its sodium salt is soluble in water and insoluble in organic solvents. The enol acetate has m. P. 117-118 °c and the ketone Formula m. P. 182-183 °c.
with corn, wheat, sorghum, corn flour as bait, add appropriate amount of sugar as attractant, with vegetable oil (about 3%) as binder, the poison bait containing 0.005%-0.025% of the active ingredient is prepared by mixing and evenly mixing in a certain proportion. In the places where the rats are frequently active, the amount of 1 feeding is basically enough for 3 days, such as family, warehouse, 60-100g of poison bait per room (15 m2), 5-8 stacks. Only after 48h of feeding, if it has been eaten, it should be replenished in time. Make sure there is sufficient bait. The efficacy can be maintained for 10-14 days.
2.5%-0.5% poison powder can be prepared by mixing raw powder or 1.0% powder with flour or talc. It is applied to the places where the rats are often active, and used as a licking agent to kill the rats.
warfarin was synthesized from benzaldehyde and acetone, and then condensed with 4-hydroxycoumarin. There are 98% raw powder, 2.5% mother powder and 0.025 poison bait. Pure Powder by starch and powder mixed uniformly. The poison bait is made of corn flour and other grains, mixed with the mother powder and the warning color, and then extruded and dried into a strip shape. The wax block poison bait can also be made by mixing the mother powder and paraffin.
preparation of 4-hydroxycoumarin with salicylic acid as raw material, first with methanol esterification, and then with acetic anhydride at 40 ℃ acylation, then under the action of metal sodium 240~250 ℃ ring closure, synthesis of 4-hydroxycoumarin by acidification. It can also be prepared by acylation, cyclization and acidification of salicylic acid and thionyl chloride.
Preparation of substituted butenes-[3]-ketones-[2]-Benzaldehyde was prepared by condensation of benzaldehyde with acetone in the presence of sodium hydroxide.
Synthesis of warfarin the above two intermediates were refluxed in pyridine for 24h to remove pyridine, poured into water, acidified to pH about 2 with hydrochloric acid, placed, solidified, and recrystallized to obtain warfarin.
category | pesticide |
toxicity grade | highly toxic |
Acute toxicity | oral-rat LD50: 1.6 mg/kg; Oral-mouse LD50: 3 mg/kg |
flammability hazard characteristics | flammable; Highly toxic smoke can be emitted in the fire scene |
storage and transportation characteristics | warehouse ventilation low temperature drying; Separate storage and transportation from food raw materials |
extinguishing agent | Sand, dry powder, foam |
Occupational criteria | TWA 0.1 mg/m3; Tel 0.3 mg/m3 |