Dipyrithione

Structural formula
General
Surname	Dipyrithione
other names	Omadine disulfide; 2,2′-dithiobis (pyridine-1-oxide);
Molecular formula	C 10 H 8 N 2 O 2 S 2
External identifiers / databases
EC number	223-024-5
ECHA InfoCard	100.020.931
PubChem	3109
Wikidata	Q17321248
properties
Molar mass	252.31 g mol −1
Physical state	firmly
Melting point	205 ° C
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Dipyrithione is a chemical compound from the group of pyridines and disulfides and a derivative of pyrithione .

Extraction and presentation

Dipyrithione can be obtained from 2-chloropyridine . This reacts with peracetic acid to form 2-chloropyridine- N -oxide and further with sodium hydrogen sulfide (NaSH) to form 2-mercaptopyridine- N -oxide , which dimerizes through reaction with chlorine and sodium hydroxide .

use

Dipyrithione is fungicidal and bactericidal and is used in photographic materials, textile processing and agriculture.

Admission

Dipyrithione is not approved as a crop protection agent in the European Union or Switzerland .

toxicology

In an experiment with mouse cells, dipyrithione led to apoptosis of cancer cells.

Individual evidence

↑ ^a ^b entry on pyrithione. In: Römpp Online . Georg Thieme Verlag, accessed on June 10, 2014.
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 853 ( preview ).
↑ Huang Huang, Yu Pan, Yin Ye, Min Gao, Zhimin Yin, Lan Luo: Dipyrithione attenuates oleic acid-induced acute lung injury . In: Pulmonary Pharmacology & Therapeutics . tape 24 , 2011, p. 74-80 , doi : 10.1016 / j.pupt.2010.09.008 ( PDF ).
^ Directorate-General for Health and Food Safety of the European Commission: EU pesticide database ; Entry in the national directory of plant protection products in Switzerland ; Retrieved June 25, 2016.
↑ Yumei Fan, Caizhi Liu, Yongmao Huang, Jie Zhang, Linlin Cai, Shengnan Wang, Yongze Zhang, Xianglin Duan, Zhimin Yin: Dipyrithione induces cell-cycle arrest and apoptosis in four cancer cell lines in vitro and inhibits tumor growth in a mouse model . In: BMC Pharmacology and Toxicology . tape 14 , no. 1 , 2013, p. 54 , doi : 10.1186 / 2050-6511-14-54 ( PDF ).

[roempp-1] try on pyrithione. In: Römpp Online . Georg Thieme Verlag, accessed on June 10, 2014.

[NV-2] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[unger-3] Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 853 ( preview ).

[4] Huang Huang, Yu Pan, Yin Ye, Min Gao, Zhimin Yin, Lan Luo: Dipyrithione attenuates oleic acid-induced acute lung injury . In: Pulmonary Pharmacology & Therapeutics . tape 24 , 2011, p. 74-80 , doi : 10.1016 / j.pupt.2010.09.008 ( PDF ).

[5] Directorate-General for Health and Food Safety of the European Commission: EU pesticide database ; Entry in the national directory of plant protection products in Switzerland ; Retrieved June 25, 2016.

[6] Yumei Fan, Caizhi Liu, Yongmao Huang, Jie Zhang, Linlin Cai, Shengnan Wang, Yongze Zhang, Xianglin Duan, Zhimin Yin: Dipyrithione induces cell-cycle arrest and apoptosis in four cancer cell lines in vitro and inhibits tumor growth in a mouse model . In: BMC Pharmacology and Toxicology . tape 14 , no. 1 , 2013, p. 54 , doi : 10.1186 / 2050-6511-14-54 ( PDF ).