Cyazofamide

Structural formula
General
Surname	Cyazofamide
other names	4-chloro-2-cyano- N , N -dimethyl-5- p -tolylimidazole-1-sulfonamide ( IUPAC ); 4-chloro-2-cyano- N , N -dimethyl-5- (4-methylphenyl) -1 H -imidazole-1-sulfonamide;
Molecular formula	C 13 H 13 ClN 4 O 2 S
Brief description	white to yellowish solid
External identifiers / databases
EC number	601-671-8
ECHA InfoCard	100.111.751
PubChem	9862076
Wikidata	Q15632870
properties
Molar mass	324.79 g mol −1
Physical state	firmly
density	1.446 g cm −3 ; approx. 550 kg / m 3 (bulk density);
Melting point	160-165 ° C
solubility	practically insoluble in water (<0.1 g l −1 at 25 ° C); soluble in dichloroethane; insoluble in toluene and hexane;
safety instructions
GHS hazard labeling from Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary Caution
H and P phrases	H: 410
	P: 261-273-302 + 352 + 312-304 + 340 + 312-391-501
Toxicological data	> 5000 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 .

Cyazofamid is a chemical compound from the group of imidazoles (cyanoimidazoles) and sulfonamides .

Extraction and presentation

Cyazofamid can be obtained by a multi-stage reaction starting from 2,2-dichloro-1- (4-methylphenyl) ethanone by dehydration , two deoxygenations and a chlorination of the imidazole ring.

properties

Cyazofamid is a flammable white to yellowish solid that is practically insoluble in water. The half-life ( DT ₅₀ ) to hydrolysis is about 25 days.

use

Cyazofamid is used as an active ingredient in crop protection products. It is a protective and limited systemic fungicide , which inhibits all development stages of fungi by influencing the respiration in the mitochondrial cytochrome bc ₁ complex . It blocks the inner docking point for ubiquinone and is therefore called a Qi inhibitor. The market launch took place in 2001.

Admission

Cyazofamid was added to the list of approved active ingredients by the EU Commission for use as a fungicide in 2003.

In a number of EU countries, including Germany and Austria, as well as Switzerland, plant protection products (e.g. Ranman) containing this active ingredient are approved.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry for CAS no. 120116-88-3 in the GESTIS substance database of the IFA , accessed on May 6, 2013(JavaScript required) .
↑ ^a ^b ^c ^d ^e ^f EPA: Pesticide Fact Sheet Cyazofamid (PDF; 199 kB), September 2004.
↑ Entry on 4-chloro-2-cyano-N, N-dimethyl-5-p-tolylimidazole-1-sulfonamide 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 .
↑ Cyazofamid data sheet from Sigma-Aldrich , accessed on May 20, 2017 ( PDF ).

↑ Ulrich Schirmer, Peter Jeschke, Matthias Witschel: Modern Crop Protection Compounds: Herbicides . John Wiley & Sons, 2012, ISBN 978-3-527-32965-6 , pp. 620 (English, limited preview in Google Book Search).

↑ EU: Review report for the active substance cyazofamid (PDF; 232 kB), November 27, 2002.

↑ EFSA: Reasoned opinion on the review of the existing maximum residue levels (MRLs) for cyazofamid according to Article 12 of Regulation (EC) No 396/2005. In: EFSA Journal. 10, 2012, doi : 10.2903 / j.efsa.2012.3065 .

^ Horst Börner, Klaus Schlueter: Plant diseases and plant protection . Springer DE, 2009, ISBN 978-3-540-49068-5 , pp. 512 ( limited preview in Google Book Search).

↑ Commission Directive 2003/23 / EC of March 25, 2003 amending Council Directive 91/414 / EEC to include the active substances imazamox, oxasulfuron, ethoxysulfuron, foramsulfuron, oxadiargyl and cyazofamid

↑ General Directorate Health and Food Safety of the European Commission: Entry on cyazofamid in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved February 20, 2016.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry for CAS no. 120116-88-3 in the GESTIS substance database of the IFA , accessed on May 6, 2013(JavaScript required) .

[EPA-2] ↑ ^a ^b ^c ^d ^e ^f EPA: Pesticide Fact Sheet Cyazofamid (PDF; 199 kB), September 2004.

[CLP_100.111.751-3] Entry on 4-chloro-2-cyano-N, N-dimethyl-5-p-tolylimidazole-1-sulfonamide 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 .

[Sigma-4] Cyazofamid data sheet from Sigma-Aldrich , accessed on May 20, 2017 ( PDF ).

[Ulrich_Schirmer,_Peter_Jeschke,_Matthias_Witschel-5] Ulrich Schirmer, Peter Jeschke, Matthias Witschel: Modern Crop Protection Compounds: Herbicides . John Wiley & Sons, 2012, ISBN 978-3-527-32965-6 , pp. 620 (English, limited preview in Google Book Search).

[EU-6] EU: Review report for the active substance cyazofamid (PDF; 232 kB), November 27, 2002.

[7] EFSA: Reasoned opinion on the review of the existing maximum residue levels (MRLs) for cyazofamid according to Article 12 of Regulation (EC) No 396/2005. In: EFSA Journal. 10, 2012, doi : 10.2903 / j.efsa.2012.3065 .

[Horst_Börner,_Klaus_Schlüter-8] Horst Börner, Klaus Schlueter: Plant diseases and plant protection . Springer DE, 2009, ISBN 978-3-540-49068-5 , pp. 512 ( limited preview in Google Book Search).

[9] Commission Directive 2003/23 / EC of March 25, 2003 amending Council Directive 91/414 / EEC to include the active substances imazamox, oxasulfuron, ethoxysulfuron, foramsulfuron, oxadiargyl and cyazofamid

[PSM-10] General Directorate Health and Food Safety of the European Commission: Entry on cyazofamid in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved February 20, 2016.