Quintozine Chemical Properties

Melting point:

140-143 °C (lit.)

Boiling point:

328°C

Density 

1.718

vapor pressure 

1.27 x l0^-2Pa (25 °C)

Flash point:

11 °C

storage temp. 

APPROX 4°C

solubility 

toluene: soluble50mg/mL, clear, faintly to slightly yellow

form 

powder

color 

yellow to tan

Water Solubility 

Insoluble

Merck 

8080

BRN 

1914324

Stability:

Stable. Incompatible with strong bases, strong oxidizing agents.

CAS DataBase Reference

82-68-8(CAS DataBase Reference)

IARC

3 (Vol. 5, Sup 7) 1987

NIST Chemistry Reference

Benzene, pentachloronitro-(82-68-8)

EPA Substance Registry System

Pentachloronitrobenzene (82-68-8)

Safety Information

Hazard Codes 

Xi,N,T,F,Xn

Risk Statements 

43-50/53-39/23/24/25-23/24/25-11-40-51/53

Safety Statements 

13-24-37-60-61-45-36/37-16-24/25-23

RIDADR 

UN 3077 9/PG 3

WGK Germany 

2

RTECS 

DA6650000

HazardClass 

9

PackingGroup 

III

HS Code 

29049090

Hazardous Substances Data

82-68-8(Hazardous Substances Data)

Toxicity

LD50 in male, female rats (g/kg): 1.71 ±0.20, 1.65 ±0.17 by gavage (Finnegan)

MSDS

• Language:English Provider:Quintozine
• Language:English Provider:SigmaAldrich

Quintozine Usage And Synthesis

Description

Pentachloronitrobenzene (PCNB) is a pesticide and fungicide. Sensitization can occur in farmers and in those working in chemical plants.

Chemical Properties

Light green powder

Chemical Properties

Quinalphos is an off-white powder. It is stable and incompatible with strong bases and strong oxidizing agents. Quinalphos is uses as a fungicide and herbicide.

Chemical Properties

Quintozene is a colorless to cream-colored crystalline material. Musty, mothball odor. Technical-grade PCNB contains an average of 97.8% PCNB, 1.8% hexa- chlorobenzene (HCB), 0.4% 2,3,4,5-tetrachloronitrobenzene (TCNB), and less than 0.1% pentachlorobenzene. Musty odor.

Chemical Properties

Pentachloronitrobenzene forms colorless needles. Technical-grade PCNB contains an average of 97.8% PCNB, 1.8% hexachlorobenzene (HCB), 0.4% 2,3,4,5-tetrachloronitrobenzene (TCNB), and less than 0.1% pentachlorobenzene.

Uses

Pentachloronitrobenzene (PCNB) is used as a fungicide to suppress the growth of fungi in selective culture media such as Nash and Snyder medium (NS).

Uses

Quintozene is used against a range of diseases on vegetables, flower crops, cotton, bulbs, potatoes, wheat, rice, peanuts, pulse crops, maize, bananas and turf. It is used in the field and in glasshouses. It is usually applied to soil or as a seed treatment.

Uses

Fungicide for seed and soil treatment.

Production Methods

Quintozine is produced by nitration of pentachlorobenzene.

Definition

ChEBI: A C-nitro compound that is nitrobenzene in which every hydrogen has been replaced by a chlorine. A fungicide used on a variety of crops, including cotton, rice and seed grains, it is no longer approved for use within the European Union.

General Description

Crystalline pale yellow to white solid or powder with a musty moth ball odor. Insoluble in water and denser than water. Hence sinks in water.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Quintozine is hydrolyzed by alkalis. Is incompatible with strong oxidizing agnets. Also incompatible with strong bases. Corrosive to unlined metal containers .

Health Hazard

Exposures to quinalphos cause toxicity and adverse health effects. On contact with the skin, quinalphos causes the effects of sensitization.

Fire Hazard

On hazardous decomposition, quintozene releases phosgene, hydrogen chloride, oxides of nitrogen, and chlorine-containing compounds, and other unknown materials may be released in a fire situation. Incomplete combustion may lead to the formation of oxides of carbon.

Agricultural Uses

Soil fungicide, Nematicide, Seed treatment: Quintozene, the common name for PCNB or pentachlkoronitrobenzene, is an organochlorine fungicide used as a seed dressing or soil treatment to control a wide range of fungi species in such crops as potatoes, wheat, onions, lettuce, tomatoes, tulips, garlic, and others. Depending on the producer and the manufacturing procedure, PCNB impurities can include hexachlorobenzene, pentachlorobenzene, and tetrachloronitrobenzene. The fungicide is often used in combination with insecticides and fungicides including carbaryl, imazalil, tridimenol, etridiazole, and fuberidazole. It is available as a dustable or wettable powder, in granular form, emulsifiable concentrate, and seed treatment. Not approved for use in EU countries. Registered for use in the U.S. and Canada. There are more than 35 global suppliers.

Trade name

(EPA lists 290 active and canceled or transferred products) AVICOL (PESTICIDE)®; BOTRILEX®; BLOCKER 4F®; BOTRILEX®; BRASSICOL®; BRASSICOL EARTHCIDE®; BRASSICOL 75®; BRASSICOL SUPER®; CHINOZAN®; EARTHCIDE®; FARTOX®; FOLOSAN®; FOMAC 2®; FUNGICHLOR®; GC 3944-3-4®; KOBU®; KOBUTOL®; KODIAK A-T FUNGICIDE®; KP 2®; MARISAN FORTE®; MEFENOXAM®; PARFLO®; PENTAGEN®; PHOMASAN®; PKhNB®; RTU 1010®; SANICLOR 30®; TERRACHLOR®; TERRACLOR®; TERRACLOR 30G®; TERRA-COAT®; TERRAFUN®; TERRAZAN®; TILCAREX®; TRIPCNB®; TRIQUINTAM®; TRITISAN®; TUBERGRAN®; TURFCIDE®; VITAVAX® Quintozene

Contact allergens

Pentachloronitrobenzene is a pesticide and a fungicide. Sensitization can occur in farmers or in chemical plants.

Safety Profile

Moderately toxic by ingestion. An experimental teratogen. Questionable carcinogen with experimental carcinogenic data. Mutation data reported. Used as a fungcide. Dangerous; when heated to decomposition it emits highly toxic fumes of NO, and Cl-. See also NITRO COMPOUNDS OF AROMATIC HYDROCARBONS

Potential Exposure

Those engaged in manufacture, formulation and application of this soil fungicide and seed treatment chemical. Peracetic acid is often used as a sterilizing agent in the medical, food service and pharmaceutical industries in combination hydrogen peroxide and acetic acid.

Environmental Fate

Biological. Pentachloronitrobenzene is rapidly degraded in flooded soils forming pentachloroaniline. When pentachloronitrobenzene was incubated in a submerged soil and moist soil for 3 weeks, the percentages of the applied dosage remaining were <1 and 82%, respectively. Chacko et al. (1966) reported microorganisms can convert pentachloronitrobenzene to pentachloroaniline and pentachlorothioanisole
Soil. The half-lives of pentachloronitrobenzene in a Columbia fine sandy loam, Sacramento clay and Staten peaty muck from California were 4.7, 7.6 and 9.7 months, respectively. Degradation products were pentachloroaniline and pentachlorothioanis
When heated to decomposition (330°C), emits toxic fumes of nitrogen oxides and chlorine (Sax and Lewis, 1987)

Metabolic pathway

Renner (1981) has reviewed the metabolism of quintozene. Fate in soil, plants, several animal species and fish has been reported. The nitro group provides a reactive centre, which allows rapid metabolism via three primary routes: nitro reduction, glutathione-dependent denitration and dechlorination. Thus a very complex array of metabolites is formed. Quintozene is relatively persistent in soil in comparison with plants and animals. It was one of the compounds which stimulated the study and understanding of the catabolism of glutathione conjugates in plants and animals and this was properly elucidated for the first time using such compounds. Nitro reduction and nitro displacement is quite rapid and therefore quintozene is much less persistent than is hexachlorobenzene. The latter shares one of the primary metabolites [ S-(pentachlorophenyl)glutathione] with quintozene and many of the sulfur-containing metabolites are common to both compounds.

Shipping

UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required. UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

Purification Methods

Crystallise it from EtOH. [Beilstein 5 H 247, 5 II 188, 5 III 618.]

Degradation

Quintozene is a stable compound. It is stable in acidic media but is hydrolysed in base (PM). The nitro group is liable to displacement by thiolysis.

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explo- sions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Thermal decomposition products may include nitrogen oxides and hydrogen chlo- ride. Corrosive to unlined metal containers .

Waste Disposal

Dispose of contents/container to an approved waste disposal plant or consult with envi- ronmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste contain- ing this contaminant (≥100 kg/mo) must conform to EPA regulations governing storage, transportation, treatment, and waste disposal. In accordance with 40CFR165, follow recommendations for the disposal.

Quintozine(82-68-8)Related Product Information

• TECNAZENE
• 2,3,4-TRICHLORONITROBENZENE
• 2,6-Dichloronitrobenzene
• 4-Chloronitrobenzene
• 2,5-Dichloroaniline
• Hydroxylamine hydrochloride
• 2,4,6-Trichloroaniline
• 2-Nitrochlorobenzene
• 3,4,5-Trichloronitrobenzene
• 2,6-DICHLORONITROSOBENZENE
• 1,2,4-Trichloro-5-nitrobenzene
• 3,4,5-TRICHLOROANILINE
• 1,2,3,4-Tetrachlorobenzene
• 1,2,4-Trichlorobenzene
• 1,3,5-Trichlorobenzene
• 2,6-Dichloroaniline
• 2,3-Dichloronitrobenzene
• 3,4-Dichloronitrobenzene