Dithianon

Structural formula
General
Surname	Dithianon
other names	2,3-dicyano-9,10-dioxo-1,4-dithiaanthracene; 2,3-dicarbonitrilo-1,4-dithiaanthraquinone; 2,3-Dinitrilo-1,4-dithiaanthraquinone; 5,10-dihydro-5,10-dioxonaphtho [2,3- b ] -1,4-dithi-yne-2,3-dicarbonitrile; Delan;
Molecular formula	C 14 H 4 N 2 O 2 S 2
Brief description	brown solid
External identifiers / databases
EC number	222-098-6
ECHA InfoCard	100.020.090
PubChem	18771
ChemSpider	17724
Wikidata	Q1230269
properties
Molar mass	296.33 g mol −1
Physical state	firmly
density	1.58 g cm −3
Melting point	225 ° C ; in technical quality 215-217 ° C;
Vapor pressure	2.71 10 −9 Pa (25 ° C)
solubility	very sparingly soluble in water: 0.14 g l −1 (20 ° C); slightly soluble in acetone and dichloromethane;
safety instructions
H and P phrases	H: 302-330-317-318-410
	P: 260-273-280-304 + 340 + 310-305 + 351 + 338 + 310-391-403 + 233
Toxicological data	638 mg kg −1 ( LD 50 , rat , oral ) ; > 2000 mg kg −1 ( LD 50 , rat , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Dithianon is a chemical compound from the group of quinones , nitriles and sulfur-containing heterocycles , which was introduced by Merck in 1962 as a foliar fungicide .

Extraction and presentation

The synthesis of dithianon starts in the first step from sodium cyanodithioformate formed by the reaction of carbon disulfide with sodium cyanide , which dimerizes with elimination of sulfur to the intermediate product of the disodium salt of 1,2-dicyano-1,2-dimercaptoethene . This then reacts with 2,3-dichloro-1,4-naphthoquinone ( dichlone ) to form the target compound.

properties

Dithianon consists of brown crystals, which are sparingly soluble in water. It decomposes before it reaches the boiling point. Four polymorphic crystal forms are known and characterized for the solid .

use

Dithianon is used as a broad spectrum fungicide (for example against coffee rust , scab in pome fruit or downy mildew [ downy mildew [ downy mildew ] in hops ). It is marketed under the trade names Aktuan , Delan , Dithianon and Agro Thianon .

Admission

In many EU countries, including Germany and Austria, as well as Switzerland, plant protection products that contain this active ingredient are approved.

proof

Dithianon can be detected by direct current polarography or spectrophotometrically .

Web links

Joint Meeting on Pesticide Residues (JMPR), Monograph for Dithianon
EPA: Dithianon: Human Health Risk Assessment for Proposed Food Uses of the Fungicide on Imported Pome Fruit and Hops ( Memento of April 12, 2013 in the Internet Archive )

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g Entry on Dithianon in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
↑ ^a ^b ^c ^d Entry on Dithianon. In: Römpp Online . Georg Thieme Verlag, accessed on May 27, 2014.
↑ ^a ^b ^c EPA: Factsheet
↑ Entry on Dithianon in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ Bähr, G .; Schleitzer, G .: Contributions to the chemistry of carbon disulfide and carbon selenium, Part I: Salts of cyano-dithioformic acid in Chem. Ber. 88 (1955) 1771-1777, doi: 10.1002 / cber.19550881129 .
↑ Bähr, G .; Schleitzer, G .: Contributions to the chemistry of carbon disulfide and carbon selenium, II. The condensing spontaneous desulfurization of cyandithioformic acid, free cyandithioformic acid in Chem. Ber. 90 (1957) 438-443, doi: 10.1002 / cber.19570900322 .
↑ Patent US2976296 : Derivatives of 1,4-dithia-anthraquinone and-hydroquinone. Published on March 21, 1961 , inventors: Ernst Jacobi, Horst Flemming, Albert Van Schoor, Siegmund Lust. ‌
↑ Thomas A. Unger: Pesticide synthesis handbook . Springer, 1996, ISBN 978-0-8155-1401-5 ( preview ).
↑ Ivan Halasz, Robert Dinnebier, Tiziana Chiodo, Heidi Saxell: Structures of four polymorphs of the pesticide dithianon solved from X-ray powder diffraction data . In: Acta Crystallographica Section B: Structural Science . tape 68 , no. 6 , December 2012, p. 661-666 , doi : 10.1107 / s0108768112036191 ( PDF ).
↑ Ullmann's Agrochemicals, Volume 1 . Viley, 2007, ISBN 978-3-527-31604-5 ( preview ).
↑ ^a ^b Directorate-General for Health and Food Safety of the European Commission: Entry on Dithianon in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 13, 2016.
^ Günter Henze: Polarography and Voltammetry: Basics and analytical practice . 2001, ISBN 978-3-540-41394-3 , pp. 132 .
↑ W. Sternik: Spectrophotometric determination of dithianon (2,3-dicyano-1,4-dithio-anthraquinone) in fungicides . In: Fresenius' Journal for Analytical Chemistry . tape 238 , no. 2 , 1968, p. 138-138 , doi : 10.1007 / bf00510635 .

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g Entry on Dithianon in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .

[roempp-2] Entry on Dithianon. In: Römpp Online . Georg Thieme Verlag, accessed on May 27, 2014.

[epa-3] EPA: Factsheet

[CLP_100.020.090-4] Entry on Dithianon in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[5] Bähr, G .; Schleitzer, G .: Contributions to the chemistry of carbon disulfide and carbon selenium, Part I: Salts of cyano-dithioformic acid in Chem. Ber. 88 (1955) 1771-1777, doi: 10.1002 / cber.19550881129 .

[6] Bähr, G .; Schleitzer, G .: Contributions to the chemistry of carbon disulfide and carbon selenium, II. The condensing spontaneous desulfurization of cyandithioformic acid, free cyandithioformic acid in Chem. Ber. 90 (1957) 438-443, doi: 10.1002 / cber.19570900322 .

[7] Patent US2976296 : Derivatives of 1,4-dithia-anthraquinone and-hydroquinone. Published on March 21, 1961 , inventors: Ernst Jacobi, Horst Flemming, Albert Van Schoor, Siegmund Lust. ‌

[unger-8] Thomas A. Unger: Pesticide synthesis handbook . Springer, 1996, ISBN 978-0-8155-1401-5 ( preview ).

[9] Ivan Halasz, Robert Dinnebier, Tiziana Chiodo, Heidi Saxell: Structures of four polymorphs of the pesticide dithianon solved from X-ray powder diffraction data . In: Acta Crystallographica Section B: Structural Science . tape 68 , no. 6 , December 2012, p. 661-666 , doi : 10.1107 / s0108768112036191 ( PDF ).

[ullmann-10] Ullmann's Agrochemicals, Volume 1 . Viley, 2007, ISBN 978-3-527-31604-5 ( preview ).

[PSM-11] Directorate-General for Health and Food Safety of the European Commission: Entry on Dithianon in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 13, 2016.

[henze-12] Günter Henze: Polarography and Voltammetry: Basics and analytical practice . 2001, ISBN 978-3-540-41394-3 , pp. 132 .

[13] W. Sternik: Spectrophotometric determination of dithianon (2,3-dicyano-1,4-dithio-anthraquinone) in fungicides . In: Fresenius' Journal for Analytical Chemistry . tape 238 , no. 2 , 1968, p. 138-138 , doi : 10.1007 / bf00510635 .