Pentachloronitrobenzene

Structural formula
General
Surname	Pentachloronitrobenzene
other names	Quintozen; PCNB;
Molecular formula	C 6 NCl 5 O 2
Brief description	colorless needles
External identifiers / databases
EC number	201-435-0
ECHA InfoCard	100.001.305
PubChem	6720
Wikidata	Q418683
properties
Molar mass	295.34 g mol −1
Physical state	firmly
density	1.718 g cm −3 (25 ° C)
Melting point	144 ° C
boiling point	328 ° C (partial decomposition)
solubility	practically insoluble in water (0.1 mg l −1 )
safety instructions
H and P phrases	H: 317-410
	P: 273-280-501
Toxicological data	1100 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Pentachloronitrobenzene (quintozene) is a chemical compound from the group of benzene derivatives .

Extraction and presentation

Pentachloronitrobenzene can be obtained by reacting chlorine with nitrobenzene .

{\ displaystyle \ mathrm {5 \ Cl_ {2} + C_ {6} H_ {5} NO_ {2} \ longrightarrow C_ {6} Cl_ {5} NO_ {2} +5 \ HCl}}

properties

Pentachloronitrobenzene is a colorless solid consisting of needle-shaped crystals that is practically insoluble in water. It decomposes when heated, producing hydrogen chloride, nitrogen oxides, carbon monoxide and carbon dioxide. Under environmental conditions it converts to pentachloroaniline . The technical product is (depending on its purity) a light yellow to whitish solid with a musty odor. It is soluble in carbon disulfide , benzene , chloroform , ketones, and aromatic or chlorinated hydrocarbons , but is practically insoluble in water.

use

Pentachloronitrobenzene is used as a medicine and in agriculture as a pesticide and disinfectant. It is used as a fungicide in the US . It was first synthesized in 1868 and introduced as a fungicide in Germany in the 1930s. It has been produced in the USA since 1962, where it was first registered in 1964. In 1972 the annual production in the USA was about 1,300 tons, of which 30-40% was exported.

Admission

The EC Commission decided in 2000 that pentachloronitrobenzene should not be included as an active ingredient in Annex I of Directive 91/414 / EEC and that all approvals as a plant protection product should be withdrawn. In Germany, Austria and Switzerland, no pesticides with this active ingredient are permitted.

literature

Toxicology and carcinogenesis studies of pentachloronitrobenzene (CAS NO. 82-68-8) in B6C3F1 Mice (Feed Studies) (PDF; 6.8 MB). In: National Toxicology Program. Technical Report Series. No. 325, January 1987, PMID 12748728 .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on pentachloronitrobenzene in the GESTIS substance database of the IFA , accessed on February 14, 2017(JavaScript required) .
↑ Entry on Quintozene in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ ^a ^b ^c ^d Environmental Health Criteria (EHC) for Quintozene , accessed November 19, 2014.
↑ Harun Parlar, Daniela Angerhöfer: Chemical Ecotoxicology . Springer DE, 1995, ISBN 3-540-59150-8 , pp. 59 ( limited preview in Google Book search).
↑ Enius: pentachloronitrobenzene
^ Robert Irving Krieger: Handbook of Pesticide Toxicology . Academic Press, 2001, ISBN 0-12-426260-0 , pp. 322 .
↑ EPA: Reregistration Eligibility Decision for Pentachloronitrobenzene (PDF; 2.9 MB)
↑ Decision of the Commission of December 27, 2000 on the non-inclusion of quintozen in Annex I of Council Directive 91/414 / EEC and the revocation of the authorizations for plant protection products with this active substance (PDF) (2000/816 / EC).
^ Directorate-General for Health and Food Safety of the European Commission: Entry on Quintozene in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 12, 2016.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on pentachloronitrobenzene in the GESTIS substance database of the IFA , accessed on February 14, 2017(JavaScript required) .

[CLP_100.001.305-2] Entry on Quintozene in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[WHO-3] Environmental Health Criteria (EHC) for Quintozene , accessed November 19, 2014.

[Harun_Parlar,_Daniela_Angerhöfer-4] Harun Parlar, Daniela Angerhöfer: Chemical Ecotoxicology . Springer DE, 1995, ISBN 3-540-59150-8 , pp. 59 ( limited preview in Google Book search).

[Enius-5] Enius: pentachloronitrobenzene

[Robert_Irving_Krieger-6] Robert Irving Krieger: Handbook of Pesticide Toxicology . Academic Press, 2001, ISBN 0-12-426260-0 , pp. 322 .

[EPA-7] EPA: Reregistration Eligibility Decision for Pentachloronitrobenzene (PDF; 2.9 MB)

[8] Decision of the Commission of December 27, 2000 on the non-inclusion of quintozen in Annex I of Council Directive 91/414 / EEC and the revocation of the authorizations for plant protection products with this active substance (PDF) (2000/816 / EC).

[PSM-9] Directorate-General for Health and Food Safety of the European Commission: Entry on Quintozene in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 12, 2016.