P,P'-DDD

Chemical properties

colourless to off-white crystals

Chemical properties

TDE is a colorless, combustible, crystalline compound.

The Uses of P,P'-DDD

4,4'-Dichlorodiphenyldichloroethane is a synthetic organochlorine insecticide. 4,4'-Dichlorodiphenyldichloroethane is a metabolite of 4,4'-Dichlorodiphenyltrichloroethane (D434195). 4,4'-Dichlorodiphenyldichloroethane is a probable carcinogen (Group B2).

The Uses of P,P'-DDD

Contact control of leaf rollers and other insects on vegetables and tobacco

Definition

ChEBI: A chlorophenylethane that is 2,2-bis(p-chlorophenyl)ethane substituted by two chloro groups at position 1. It is a metabolite of the organochlorine insecticide, DDT.

General Description

A colorless crystalline solid. Insoluble in water and sinks in water. Toxic by inhalation, skin absorption or ingestion. Used as a pesticide.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

TDE is a halogenated hydrocarbon. Compounds in this group may react with acids, bases, and oxidizing and reducing agents. They are incompatible with alkali, and strong oxidizers, in particular.

Hazard

Toxic by ingestion, inhalation, and skin absorption; use restricted in some states. Questionable carcinogen.

Health Hazard

A derivative of DDT; toxic properties similar to DDT; systemic effects from ingestion include headache, anesthesia, cardiacarrhythmias, nausea, vomiting, sweating,and convulsions; oral lethal dose in mice600 mg/kg; also moderately toxic by skinabsorption; susceptible to accumulation infat; sufficient evidence of carcinogenicity inexperimental animals.
LD50 oral (rat): 113 mg/kg
LD50 skin (rabbit): 1200 mg/kg.

Fire Hazard

Special Hazards of Combustion Products: Irritating hydrogen chloride fumes may form in fires.

Safety Profile

Confirmed carcinogen withexperimental carcinogenic, neoplastigenic, andtumorigenic data. Poison by ingestion. Moderately toxicby skin contact. Mutation data reported. An insecticide.When heated to decomposition it emits toxic fumes ofCl-.

Potential Exposure

A potential danger to those involved in the manufacture, formulation and application of this insecticide. In an action of March 18, 1971, EPA cancelled all pesticide uses of this product which is a metabolite of DDT. Hence it is no longer manufactured commercially.

Environmental Fate

Biological. It was reported that p,p′-DDD, a major biodegradation product of p,p′- DDT, was degraded by Aerobacter aerogenes under aerobic conditions to yield 1-chloro- 2,2-bis(p-chlorophenyl)ethylene, 1-chloro-2,2-bis-(p-chlorophenyl)ethane and 1,1-bis(pchlorophenyl)ethylene. Under anaerobic conditions, however, four additional compounds were identified: bis(p-chlorophenyl)acetic acid, p,p′-dichlorodiphenylmethane, p,p′- dichlorobenzhydrol and p,p′-dichlorobenzophenone (Fries, 1972). Under reducing conditions, indigenous microbes in Lake Michigan sediments degraded DDD to 2,2-bis(pchlorophenyl)ethane and 2,2-bis(p-chlorophenyl)ethanol (Leland et al., 1973). Incubation of p,p′-DDD with hematin and ammonia gave 4,4′-dichlorobenzophenone, 1-chloro-2,2- bis-(p-chlorophenyl)ethylene and bis(p-chlorophenyl)acetic acid methyl ester (Quirke et al., 1979). Using settled domestic wastewater inoculum, p,p′-DDD (5 and 10 mg/L) did not degrade after 28 days of incubation at 25°C (Tabak et al., 1981).
Chemical/Physical. The hydrolysis rate constant for p,p′-DDD at pH 7 and 25°C was determined to be 2.8 × 10–6/hour, resulting in a half-life of 28.2 years (Ellington et al., 1987). 2,2-Bis(4-chlorophenyl)-1-chloroethene and hydrochloric acid were

Shipping

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. UN2761 Organochlorine pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.

Purification Methods

Crystallise DDD from EtOH and dry it in vacuo. The purity is checked by TLC. [Beilstein 5 III 1830.] TOXIC INSECTICIDE.

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides.

Waste Disposal

Incineration in a unit operating above 850℃ equipped with HCl scrubber. Incineration above 1200℃ for 1-2 seconds is recommended. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office.