Azoxystrobin

Structural formula
General
Surname	Azoxystrobin
other names	Methyl ( E ) -2- {2- [6- (2-cyanophenoxy) pyrimidin-4-yloxyl] phenyl} -3-methoxyacrylate ( IUPAC )
Molecular formula	C 22 H 17 N 3 O 5
Brief description	dark orange to brown solid
External identifiers / databases
EC number	603-524-3
ECHA InfoCard	100.127.964
PubChem	3034285
ChemSpider	2298772
DrugBank	DB07401
Wikidata	Q2013860
properties
Molar mass	403.39 g mol −1
Physical state	firmly
density	1.34 g cm −3
Melting point	114-116 ° C
solubility	practically insoluble in water (6.7 mg l −1 at 20 ° C)
safety instructions
H and P phrases	H: 331-410
	P: 261-273-311-501
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 .

Azoxystrobin is a chemical compound from the group of strobilurins and methoxyacrylates that is used as a fungicide in agriculture. The compound was developed by Imperial Chemical Industries (then AstraZeneca , now Syngenta ) and launched in 1996.

Extraction and presentation

Azoxystrobin is made from 3H -benzofuran-2-one.

Mode of action and application

Estimated US application rate in 2011

Azoxystrobin works by inhibiting cytochrome c reductase at the Q _o site and thus blocks cell respiration in the mitochondria of the fungi. This inhibits the germination and development of the spores.

The fungicide is used in a number of crops, such as grain , rice , fruit , potatoes , tomatoes and against fungal infections in viticulture .

Environmental aspects

Azoxystrobin is toxic to aquatic organisms, but is not dangerous to bees; also earthworms , hover flies and parasitic wasps are not damaged. Degradation in the soil as well as in plants occurs rapidly with a half-life of 3 to 39 days in the soil.

Admission

The active ingredient azoxystrobin was added to the list of active ingredients of plant protection products permitted in the European Union in 1998. The drug approval was extended several times, in 2011 the EU Commission also set a maximum value for the contamination toluene and stricter protection of aquatic organisms.

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

Trade names

Amistar, Quadris, Ortiva, Pyroxystrobin

Individual evidence

↑ ^a ^b ^c ^d Entry on azoxystrobin in the GESTIS substance database of the IFA , accessed on February 6, 2017(JavaScript required) .
↑ ^a ^b ^c ^d EU: Review report for the active substance azoxystrobin (PDF; 583 kB)
↑ Entry on azoxystrobin (ISO) 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 ^e entry on azoxystrobin. In: Römpp Online . Georg Thieme Verlag, accessed on August 28, 2013.
↑ Wolfgang Krämer, Ulrich Schirmer, Peter Jeschke, Matthias Witschel: Modern Crop Protection Compounds: Herbicides, Volume 1 . Wiley-VCH, 2011, ISBN 978-3-527-32965-6 , pp. 617 ( limited preview in Google Book search).
↑ Directive 98/47 / EC of the Commission of June 25, 1998 (PDF) for the inclusion of the active substance azoxystrobin in Annex I of Directive 91/414 / EEC of the Council on the placing of plant protection products on the market.
↑ Implementing regulation (EU) No. 703/2011 of the Commission of July 20, 2011 (PDF) for the approval of the active substance azoxystrobin according to Regulation (EC) No. 1107/2009 of the European Parliament and of the Council on the placing of plant protection products on the market and amending it of the Annex of the Commission Implementing Regulation (EU) No. 540/2011.
^ Directorate-General for Health and Food Safety of the European Commission: Entry on azoxystrobin in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 13, 2016.

[GESTIS-1] Entry on azoxystrobin in the GESTIS substance database of the IFA , accessed on February 6, 2017(JavaScript required) .

[eu-2] EU: Review report for the active substance azoxystrobin (PDF; 583 kB)

[CLP_100.127.964-3] Entry on azoxystrobin (ISO) 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 .

[roempp-4] ↑ ^a ^b ^c ^d ^e entry on azoxystrobin. In: Römpp Online . Georg Thieme Verlag, accessed on August 28, 2013.

[mcp-5] Wolfgang Krämer, Ulrich Schirmer, Peter Jeschke, Matthias Witschel: Modern Crop Protection Compounds: Herbicides, Volume 1 . Wiley-VCH, 2011, ISBN 978-3-527-32965-6 , pp. 617 ( limited preview in Google Book search).

[6] Directive 98/47 / EC of the Commission of June 25, 1998 (PDF) for the inclusion of the active substance azoxystrobin in Annex I of Directive 91/414 / EEC of the Council on the placing of plant protection products on the market.

[7] Implementing regulation (EU) No. 703/2011 of the Commission of July 20, 2011 (PDF) for the approval of the active substance azoxystrobin according to Regulation (EC) No. 1107/2009 of the European Parliament and of the Council on the placing of plant protection products on the market and amending it of the Annex of the Commission Implementing Regulation (EU) No. 540/2011.

[PSM-8] Directorate-General for Health and Food Safety of the European Commission: Entry on azoxystrobin in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 13, 2016.