| Description | Diphacinone is also called 2-(diphenylacetyl)indan-1,3-dione,is a yellow powderwhich is practically insoluble in water, readily solublein chloroform, toluene, xylene, acetone, ethanol, heptane,alkalis [9, p. 431]. |
| Originator | Dipaxin,Upjohn,US,1955 |
| Uses | Rodenticide. |
| Uses | Diphacinone is used for the control of rats, mice, voles, prairiedogs, ground squirrels and other rodents. |
| Uses | Diphacinone is an anticoagulant rodenticide widely used to control rodent infestations. |
| Production Methods | Diphacinone is produced by condensation of 1,1-diphenylacetone with dimethyl phthalate in the presence of sodiummethoxide (30). |
| Definition | ChEBI: Diphenadione is a diarylmethane and a beta-triketone. |
| Manufacturing Process | A solution of sodium methoxide was prepared by adding 2.76 grams (0.12mol) of sodium to 50 ml of absolute methanol and gently warming themixture to effect complete solution of the sodium. To this was added 300milliliters of dry benzene with vigorous stirring, whereafter excess methanolwas removed by concentrating the mixture to a volume of about 100 ml. Tothe resulting sodium methoxide suspension was added a solution of 19.4grams (0.1 mol) of dimethyl phthalate in 200 ml of dry benzene. The mixturewas heated to boiling and a solution of 21 grams (0.1 mol) of diphenylacetonein 200 ml of dry benzene was added dropwise thereto. During additionapproximately 200 ml of liquid, which consisted of benzene together withmethanol formed during the course of the reaction, was distilled from thereaction mixture. After addition of the diphenylacetone, the mixture washeated under reflux for about 6 hours, cooled and stirred vigorously with 200ml of 5% sodium hydroxide solution.
The light yellow solid which separated was collected by filtration; the filtratewas reserved for treatment as described below. Suspension in water of thesolid, which weighed 12 grams, and acidification of the mixture with dilutehydrochloric acid produced a gum which soon crystallized. Recrystallization ofthis solid from ethanol gave 10.2 grams (30%) of 2-diphenylacetyl-1,3-indandione as a light yellow crystalline solid, which melted at 146-147°C.
The filtrate mentioned above consisted of 3 layers. An oily layer which waspresent between the aqueous and benzene layers was separated, acidified andextracted with ether. The aqueous layer was likewise separated, acidified andextracted with ether. The extracts were combined, dried and evaporated toyield a heavy gum which was crystallized from ethanol to give an additional2.5 grams of product which melted at 146-147°C. The total yield of 2-diphenylacetyl-1,3-indandione was 12.7 grams (37%). |
| Therapeutic Function | Anticoagulant |
| General Description | Odorless pale yellow crystals. Used as a rodenticide and anticoagulant medication. |
| Air & Water Reactions | Practically insoluble in water (17mg/L). Hydrolyzed by strong acid. |
| Reactivity Profile | DIPHACINONE is a ketone, and behaves as a weak acid. Forms water soluble alkali metal salts. Ketones are reactive with many acids and bases liberating heat and flammable gases (e.g., H2). The amount of heat may be sufficient to start a fire in the unreacted portion of the ketone. Ketones react with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat. Ketones are incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides. They react violently with aldehydes, HNO3, HNO3 + H2O2, and HClO4. |
| Health Hazard | DIPHACINONE is extremely toxic; probable oral lethal dose in humans is 5-50 mg/kg, or between 7 drops and 1 teaspoonful for a 150-lb. person. Many medical conditions will be aggravated by DIPHACINONE. |
| Fire Hazard | When heated to decomposition DIPHACINONE emits acrid smoke and fumes. Sensitive to light. |
| Agricultural Uses | Rodenticide: A U.S. EPA restricted Use Pesticide (RUP) whenthe formulation contains 3% or more of diphacinone.Diphacinone is an anti-coagulant rodenticide bait used forcontrol of rats, mice, voles and other rodents. It is availablein meal, pellet, wax block, and liquid bait formulations, aswell as in tracking powder and concentrate formulations.It is used in general agriculture and in food-processing areas. The top five uses for diphacinone in California are onlandscapes, general vertebrate pest control, around structures and right of ways, and on oranges. This material isalso used as an anticoagulant medication. Not approved foruse in EU countries. |
| Trade name | DE-PESTER®[C]; DIDANDIN®;DIPAXIN®; DITRAC®; GOLD CREST®; KILL-RORAT KILLER®; LIQUA-TOX®, diphacinone sodiumsalt; ORAGULANT®; P. C. Q. ®; PID®; PROMAR®;RAMIK®; RAT KILLER®; RODENT CAKE®[C];SOLVAN®; TOMCAT®; U 1363® |
| Safety Profile | Poison by ingestion. Inlxbits blood clotting, leading to hemorrhages. Action similar to coumadin (warfarin). A pesticide used in rodent control. When heated to decomposition it emits acrid smoke and irritating fumes |
| Potential Exposure | This material is used as a rodenticideand as an anticoagulant medication. |
| First aid | If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attenti decontamination and life support for the victims.Emergency personnel should wear protective clothingappropriate to the type and degree of contamination. Airpurifying or supplied-air respiratory equipment should alsobe worn, as necessary. Rescue vehicles should carry supplies, such as plastic sheeting and disposable plastic bags,to assist in preventing spread of contaminationon immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit.Obtain authorization and/or further instructions from thelocal hospital for administration of an antidote or performance of other invasive procedures. Rush to a health-carefacility. Acute exposure to Diphacinone may require |
| Metabolic pathway | Diphacinone is a member of the indandione class of anti-coagulants.Its fate in rats and mice has been reported but no information on itsdegradation in soil or plants has been published. It is metabolised byhydroxylation and conjugation. |
| storage | Color Code—Blue: Health Hazard/Poison: Storein a secure poison location. Prior to working with thischemical you should be trained on its proper handling andstorage. Store in tightly closed containers in a cool, wellventilated area |
| Shipping | Coumarin-derivative pesticides, solid, toxic,require a shipping label of “POISONOUS/TOXICMATERIALS.” It falls in Hazard Class 6.1 and diphacinonein Packing Group I |
| Degradation | Diphacinone is stable in solution at pH 6-9 for 14 days; it is hydrolysed inless than 24 hours at pH 4 (PM). It is rapidly degraded under conditions ofaqueous photolysis (PM). |
| Incompatibilities | This material is extremely toxic;probable oral lethal dose in humans is 550 mg/kg, orbetween 7 drops and 1 teaspoonful for a 150-lb person.Diphacinone is an anticoagulant (inhibits blood clotting).Hemorrhage is the most common effect and may be manifested by nose bleeding, gum bleeding, bloody stools andurine, ecchymoses (extravasations of blood into skin), andhemoptysis (coughing up blood). Bruising is heightened.Abdominal and flank pains are also common. Other signsand symptoms include flushing, dizziness, hypotension (lowblood pressure), dyspnea (shortness of breath), cyanosis (bluetint to the skin and mucous membranes), fever, and diarrhea |
