2,3-Dichloro-1,4-naphthoquinone

Chemical properties

YELLOW FINE CRYSTALLINE POWDER

The Uses of 2,3-Dichloro-1,4-naphthoquinone

Fungicide for agriculture and textiles; herbicide.

The Uses of 2,3-Dichloro-1,4-naphthoquinone

Fungicide used on fruits, field crops and vegetables

The Uses of 2,3-Dichloro-1,4-naphthoquinone

Use in textiles, as organic catalyst, as chemical intermediate, as additive in dye binders. Also used as an important catalyst to produce 3,3-dichlorobenzene.

General Description

2,3-Dichloro-1,4-naphthoquinone is a yellow crystalline solid dissolved in a water-emulsifiable liquid carrier. Can cause illness by inhalation, skin absorption and/or ingestion. The primary hazard is the threat to the environment. Immediate steps should be taken to limit its spread to the environment. Can easily penetrate the soil and contaminate groundwater and nearby streams. Used as a fungicide.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

2,3-Dichloro-1,4-naphthoquinone is a halogenated ketone. 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

INHALATION: Irritation to mucous membrane. EYES: Irritation. SKIN: Irritation. INGESTION: Can cause CNS depression.

Fire Hazard

Special Hazards of Combustion Products: Highly toxic fumes are imminent.

Flammability and Explosibility

Not classified

Agricultural Uses

Fungicide: Not currently registered in the U.S. Not approved for use in the EU. Dichlone is used as a fungicide for foliage and to control blue algae in ponds, swimming pools and lakes. As a substitute for copper and sulfur to control rot on fruit trees, vegetables, field crops, ornamentals, resident and commercial outdoor areas.

Trade name

ALGISTAT®; COMPOUND 604®; PHYGON®; PHYGON® PASTE; PHYGON® SEED PROTECTANT; PHYGON® XL; QUINTAR®; QUINTAR® 540F; SANQUINON®; UNIROYAL® 604; USR® 604; U.S. RUBBER® 604

Safety Profile

Poison by ingestion and intraperitoneal routes. Mildly toxic by skin contact. A skin, eye, and mucous membrane irritant. Large doses can cause central nervous system depression. Questionable carcinogen with experimental carcinogenic and neoplastigenic data. A fungcide and algicide. When heated to decomposition it emits toxic fumes of Cl-. See also CHLORIDES.

Environmental Fate

Plant. In plants, dichlone loses both chlorine atoms and are replaced by sulphydryl groups to give a substituted dimercapto compound (Hartley and Kidd, 1987).
Photolytic. The UV absorption band for dichlone is 330 nm (Gore et al., 1971). Irradiation of dichlone in a variety of organic solvents (benzene, isopropanol, ethanol) using UV light produced a number of dehalogenated compounds. In the absence or presence of oxygen, 2-chloro-1,4-naphthoquinone, 1,4-naphthoquinone and 1,4-naphthalenediol were produced. Further irradiation in the presence of oxygen yielded phthalic acid and phthalic anhydride as the major products. In a mixture of benzene and isopropanol, dichlone degraded to the minor products: 2-chloro-3-hydroxy-1,4-naphthoquinone, 2- chloro-3-phenoxy-1,4-naphthoquinone, 2,3-dichloro-4-hydroxy-1-keto-2-phenyl-1,2- dihydronaphthalene and isopropyl-1-chloro-2,3-dioxo-1-indanecarboxylate (Ide et al., 1979).
Chemical/Physical. Emits toxic fumes of chlorine when heated to decomposition (Sax and Lewis, 1987).

Purification Methods

Crystallise the quinone from EtOH. [Beilstein 7 IV 2426.]