DIPHACINONE

Description

Diphacinone is also called 2-(diphenylacetyl)indan-1,3-dione, is a yellow powder which is practically insoluble in water, readily soluble in chloroform, toluene, xylene, acetone, ethanol, heptane, alkalis [9, p. 431].

Originator

Dipaxin,Upjohn,US,1955

The Uses of DIPHACINONE

Diphacinone is an anticoagulant rodenticide widely used to control rodent infestations.

The Uses of DIPHACINONE

Rodenticide.

The Uses of DIPHACINONE

Diphacinone is used for the control of rats, mice, voles, prairie dogs, ground squirrels and other rodents.

What are the applications of Application

Diphacinone is an anticoagulant rodenticide used to control infestations

Production Methods

Diphacinone is produced by condensation of 1,1-diphenyl acetone with dimethyl phthalate in the presence of sodium methoxide (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 the mixture to effect complete solution of the sodium. To this was added 300 milliliters of dry benzene with vigorous stirring, whereafter excess methanol was removed by concentrating the mixture to a volume of about 100 ml. To the resulting sodium methoxide suspension was added a solution of 19.4 grams (0.1 mol) of dimethyl phthalate in 200 ml of dry benzene. The mixture was heated to boiling and a solution of 21 grams (0.1 mol) of diphenylacetone in 200 ml of dry benzene was added dropwise thereto. During addition approximately 200 ml of liquid, which consisted of benzene together with methanol formed during the course of the reaction, was distilled from the reaction mixture. After addition of the diphenylacetone, the mixture was heated under reflux for about 6 hours, cooled and stirred vigorously with 200 ml of 5% sodium hydroxide solution.
The light yellow solid which separated was collected by filtration; the filtrate was reserved for treatment as described below. Suspension in water of the solid, which weighed 12 grams, and acidification of the mixture with dilute hydrochloric acid produced a gum which soon crystallized. Recrystallization of this 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 was present between the aqueous and benzene layers was separated, acidified and extracted with ether. The aqueous layer was likewise separated, acidified and extracted with ether. The extracts were combined, dried and evaporated to yield a heavy gum which was crystallized from ethanol to give an additional 2.5 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) when the formulation contains 3% or more of diphacinone. Diphacinone is an anti-coagulant rodenticide bait used for control of rats, mice, voles and other rodents. It is available in meal, pellet, wax block, and liquid bait formulations, as well 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 on landscapes, general vertebrate pest control, around structures and right of ways, and on oranges. This material is also used as an anticoagulant medication. Not approved for use in EU countries.

Trade name

DE-PESTER®[C]; DIDANDIN®; DIPAXIN®; DITRAC®; GOLD CREST®; KILL-RO RAT KILLER®; LIQUA-TOX®, diphacinone sodium salt; 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 its degradation in soil or plants has been published. It is metabolised by hydroxylation 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 in less than 24 hours at pH 4 (PM). It is rapidly degraded under conditions of aqueous 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