Picoxystrobin

Structural formula
General
Surname	Picoxystrobin
other names	Methyl ( E ) -α-methoxymethylene-2- (3-trifluoromethyl-2-pyridyloxymethyl) phenyl acetate; Methyl ( E ) -3-methoxy-2- {2- [6- (trifluoromethyl) -2-pyridyloxymethyl] phenyl} acrylate ( IUPAC );
Molecular formula	C 18 H 16 F 3 NO 4
Brief description	off-white odorless solid
External identifiers / databases
EC number	601-478-9
ECHA InfoCard	100.110.665
PubChem	14255373
Wikidata	Q15632879
properties
Molar mass	367.32 g mol −1
Physical state	firmly
density	1.40 g cm −3
Melting point	75 ° C
Vapor pressure	5.5 10 −9 kPa (20 ° C)
solubility	practically insoluble in water (3.1 mg l −1 at 20 ° C); soluble in 1,2-dichloroethane , acetone , ethyl acetate and xylene ;
safety instructions
H and P phrases	H: 319-332-400
	P: 273-305 + 351 + 338
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 .

Picoxystrobin is a chemical compound from the group of strobilurins and methoxyacrylates .

Extraction and presentation

Picoxystrobin can be obtained through a multi-stage reaction starting from 3-isochromanone .

properties

Picoxystrobin is an off-white, odorless solid that is practically insoluble in water. It is stable to hydrolysis at pH values of 5 and 7. The half-life to hydrolysis at a pH value of 9 and to photolysis is more than two weeks.

use

Picoxystrobin is used as a fungicide against certain fungal diseases in wheat and barley. It blocks the transport of electrons between cytochrome b and cytochrome c1 , which leads to the inhibition of ATP formation. The withdrawal of ATP hinders cellular processes, such as spore germination and mycelium growth.

Admission

Picoxystrobin was approved in Germany since 2001. However, the approvals of all plant protection products with this active ingredient expired at the end of 2017 because the EU Commission did not extend the approval of the active ingredient.

The approval by the EU Commission as an active ingredient in pesticides for use as a fungicide took effect at the beginning of 2004. In August 2017, the EU Commission decided not to renew the approval of the active ingredient.

In Switzerland, plant protection products with this active ingredient are approved.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f EU: Review report for the active substance picoxystrobin (PDF; 87 kB), June 3, 2003.
↑ ^a ^b ^c ^d ^e ^f Datasheet Picoxystrobin from Sigma-Aldrich , accessed on May 20, 2017 ( PDF ).
↑ Wolfgang Krämer, Ulrich Schirmer, Peter Jeschke, Matthias Witschel: Modern Crop Protection Compounds . Wiley-VCH, 2011, ISBN 978-3-527-32965-6 ( page 617 in the Google book search).
↑ Review of the existing maximum residue levels (MRLs) for picoxystrobin according to Article 12 of Regulation (EC) No 396/2005. In: EFSA Journal. 9, 2011, p. 2488, doi : 10.2903 / j.efsa.2011.2488 .
↑ Peter Brandt: Reports on Plant Protection Products 2009: Active Ingredients in Plant Protection Products ; Approval history and regulations of the Plant Protection Application Ordinance . Springer DE, 2010, ISBN 3-0348-0028-2 , pp. 23 ( limited preview in Google Book search).
↑ BVL - Technical reports: Revocation of the approval of plant protection products with the active ingredient picoxystrobin on November 30, 2017. Accessed on October 25, 2017 .
↑ Commission Directive 2003/84 / EC of September 25, 2003 (PDF) amending Council Directive 91/414 / EEC to include the active substances Flurtamone, Flufenacet, Iodosulfuron, Dimethenamid-p, Picoxystrobin, Fosthiazate and Silthiofam.
↑ Implementing Regulation (EU) 2017/1455 of the Commission of 10 August 2017 (PDF) on the non-renewal of the approval for the active substance picoxystrobin 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 for Amendment to the annex of Commission Implementing Regulation (EU) No. 540/2011.
↑ General Directorate Health and Food Safety of the European Commission: Entry on picoxystrobin in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on December 6, 2019.

[EU-1] ↑ ^a ^b ^c ^d ^e ^f EU: Review report for the active substance picoxystrobin (PDF; 87 kB), June 3, 2003.

[Sigma-2] ↑ ^a ^b ^c ^d ^e ^f Datasheet Picoxystrobin from Sigma-Aldrich , accessed on May 20, 2017 ( PDF ).

[modern-3] Wolfgang Krämer, Ulrich Schirmer, Peter Jeschke, Matthias Witschel: Modern Crop Protection Compounds . Wiley-VCH, 2011, ISBN 978-3-527-32965-6 ( page 617 in the Google book search).

[EFSA-4] Review of the existing maximum residue levels (MRLs) for picoxystrobin according to Article 12 of Regulation (EC) No 396/2005. In: EFSA Journal. 9, 2011, p. 2488, doi : 10.2903 / j.efsa.2011.2488 .

[Peter_Brandt-5] Peter Brandt: Reports on Plant Protection Products 2009: Active Ingredients in Plant Protection Products ; Approval history and regulations of the Plant Protection Application Ordinance . Springer DE, 2010, ISBN 3-0348-0028-2 , pp. 23 ( limited preview in Google Book search).

[6] BVL - Technical reports: Revocation of the approval of plant protection products with the active ingredient picoxystrobin on November 30, 2017. Accessed on October 25, 2017 .

[7] Commission Directive 2003/84 / EC of September 25, 2003 (PDF) amending Council Directive 91/414 / EEC to include the active substances Flurtamone, Flufenacet, Iodosulfuron, Dimethenamid-p, Picoxystrobin, Fosthiazate and Silthiofam.

[8] Implementing Regulation (EU) 2017/1455 of the Commission of 10 August 2017 (PDF) on the non-renewal of the approval for the active substance picoxystrobin 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 for Amendment to the annex of Commission Implementing Regulation (EU) No. 540/2011.

[PSM-9] General Directorate Health and Food Safety of the European Commission: Entry on picoxystrobin in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on December 6, 2019.