Cymoxanil

Structural formula
General
Surname	Cymoxanil
other names	2-cyano- N - [(ethylamino) carbonyl] -2- (methoxyimino) acetamide; Curzate;
Molecular formula	C 7 H 10 N 4 O 3
Brief description	colorless and odorless solid
External identifiers / databases
EC number	261-043-0
ECHA InfoCard	100.055.476
PubChem	5364079
Wikidata	Q1147902
properties
Molar mass	198.18 g mol −1
Physical state	firmly
density	1.31 g cm −3 (bulk density)
Melting point	160-161 ° C
solubility	very sparingly soluble in water (0.1 g l −1 at 25 ° C); soluble in acetone, acetonitrile and dichloromethane;
safety instructions
H and P phrases	H: 302-317-361fd-373-410
	P: 201-273-280-308 + 313-333 + 313-391
Toxicological data	1100 mg kg −1 ( LD 50 , rat , oral ) ; 3000 mg kg −1 ( LD 50 , rabbit , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Cymoxanil is a chemical compound from the group of cyanohydroxyiminoacetamides or urea derivatives .

Extraction and presentation

Cymoxanil can be prepared by the nitration of 1- (2-cyanoacetyl) -3-ethyl-urea with sodium nitrite in water, followed by O - methylation of oximes with a methylating agent such as iodomethane or dimethyl sulfate are obtained.

properties

Cymoxanil is a colorless and odorless solid that is insoluble in water. It is stable to hydrolysis, but unstable when exposed to UV light.

use

Cymoxanil is used as a fungicide against Oomycota , especially against downy mildew and late blight . It was developed by DuPont and launched in 1977.

Cymoxanil has a strong curative (healing) effect.

Admission

The active ingredient cymoxanil was approved for use as a fungicide in the European Union with effect from September 1, 2009.

In many EU countries, including Germany, Austria and Switzerland, various plant protection products with this active ingredient are approved.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g Entry on cymoxanil in the GESTIS substance database of the IFA , accessed on July 23, 2016(JavaScript required) .
↑ ^a ^b Data sheet Cymoxanil, PESTANAL at Sigma-Aldrich , accessed on May 19, 2017 ( PDF ).
↑ Entry on cymoxanil. In: Römpp Online . Georg Thieme Verlag, accessed on December 15, 2014.
↑ ^a ^b ^c ^d Wolfgang Krämer, Ulrich Schirmer, Peter Jeschke, Matthias Witschel: Modern Crop Protection Compounds . John Wiley & Sons, 2012, ISBN 978-3-527-32965-6 , pp. 865 ( limited preview in Google Book search).
↑ Entry on 2-cyano-N - [(ethylamino) carbonyl] -2- (methoxyimino) acetamide Template: Linktext-Check / Escaped in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can use the harmonized classification and labeling expand .
↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1401-8 , pp. 222 ( limited preview in Google Book search).
↑ ^a ^b Entry on cymoxanil in the Hazardous Substances Data Bank , accessed October 22, 2012.
↑ Jean-Luc Genet, Olivier Vincent: Sensitivity of European populations to cymoxanil . In: Pesticide Science . tape 55 , no. 2 , February 1999, p. 129-136 , doi : 10.1002 / (SICI) 1096-9063 (199902) 55: 2 <129 :: AID-PS884> 3.0.CO; 2-H ( PDF ).
↑ Directive 2008/125 / EC of the Commission of December 19, 2008 amending Council Directive 91/414 / EEC to include aluminum phosphide, calcium phosphide, magnesium phosphide, cymoxanil, dodemorph, 2,5-dichlorobenzoic acid methyl ester, metamitron, sulcotrione, Tebuconazole and Triadimenol as active ingredients (PDF)
↑ General Directorate Health and Food Safety of the European Commission: Entry on Cymoxanil in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 17, 2016.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g Entry on cymoxanil in the GESTIS substance database of the IFA , accessed on July 23, 2016(JavaScript required) .

[Sigma-2] Data sheet Cymoxanil, PESTANAL at Sigma-Aldrich , accessed on May 19, 2017 ( PDF ).

[3] Entry on cymoxanil. In: Römpp Online . Georg Thieme Verlag, accessed on December 15, 2014.

[Wolfgang_Krämer,_Ulrich_Schirmer,_Peter_Jeschke,_Matthias_Witschel-4] Wolfgang Krämer, Ulrich Schirmer, Peter Jeschke, Matthias Witschel: Modern Crop Protection Compounds . John Wiley & Sons, 2012, ISBN 978-3-527-32965-6 , pp. 865 ( limited preview in Google Book search).

[CLP_100.055.476-5] Entry on 2-cyano-N - [(ethylamino) carbonyl] -2- (methoxyimino) acetamide Template: Linktext-Check / Escaped in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can use the harmonized classification and labeling expand .

[Thomas_A._Unger-6] Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1401-8 , pp. 222 ( limited preview in Google Book search).

[HSDB-7] Entry on cymoxanil in the Hazardous Substances Data Bank , accessed October 22, 2012.

[8] Jean-Luc Genet, Olivier Vincent: Sensitivity of European populations to cymoxanil . In: Pesticide Science . tape 55 , no. 2 , February 1999, p. 129-136 , doi : 10.1002 / (SICI) 1096-9063 (199902) 55: 2 <129 :: AID-PS884> 3.0.CO; 2-H ( PDF ).

[9] Directive 2008/125 / EC of the Commission of December 19, 2008 amending Council Directive 91/414 / EEC to include aluminum phosphide, calcium phosphide, magnesium phosphide, cymoxanil, dodemorph, 2,5-dichlorobenzoic acid methyl ester, metamitron, sulcotrione, Tebuconazole and Triadimenol as active ingredients (PDF)

[PSM-10] General Directorate Health and Food Safety of the European Commission: Entry on Cymoxanil in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 17, 2016.