Trifloxystrobin

Structural formula
General
Surname	Trifloxystrobin
other names	Methyl ( E ) -methoxyimino - {( E ) -α- [1- (α, α, α-trifluoro- m -tolyl) ethylideneaminooxy] - o -tolyl} acetate; Trifloxistrobin;
Molecular formula	C 20 H 19 F 3 N 2 O 4
Brief description	colorless and odorless solid
External identifiers / databases
EC number	604-237-6
ECHA InfoCard	100.119.778
PubChem	11664966
Wikidata	Q15090829
properties
Molar mass	408.37 g mol −1
Physical state	firmly
density	1.36 g cm −3
Melting point	72.9 ° C
Vapor pressure	3.4 10 −6 Pa (° C)
solubility	practically insoluble in water; soluble in toluene, ethyl acetate, acetone and dichloromethane;
safety instructions
H and P phrases	H: 317-410
	P: 273-280-501
Toxicological data	> 5000 mg kg −1 ( LD 50 , rat , oral ) ; > 2000 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 .

Trifloxystrobin is a chemical compound from the group of strobilurins that is used in agriculture against fungal diseases in plants.

Extraction and presentation

Trifloxystrobin can be obtained by reacting methyl (2 E ) -2- (2- (chloromethyl) phenyl) -2-methoxyiminoacetate with sodium 3- (trifluoromethyl) acetophenone oxime.

properties

Trifloxystrobin is a colorless and odorless solid in its pure form. Only the E , E isomer of the compound is referred to as trifloxystrobin . It is stable to hydrolysis at pH 5 and 7, but decomposes at pH 9. When exposed to light, isomerization to the other isomers ( E , Z , Z , E , Z , Z ) on.

use

Estimated US application rate in 2011

Trifloxystrobin is used as an active ingredient in crop protection products . It is a mesostemic fungicide of the strobilurine group with an oxime ether side chain. Trifloxystrobin has a broad effect against fungal diseases in many types of fruit, vegetables and cereals. It was launched in 1999.

Admission

In 2003, the EU Commission included trifloxystrobin in the list of permitted active ingredients in plant protection products for use as a fungicide. In 2012, the permit was initially extended to the end of July 2016. In 2016 and 2017 the term of the permit was extended by one year each. In 2018, the approval for the EU was renewed, it is limited to July 2033. In a number of EU countries, including Germany and Austria, as well as Switzerland, plant protection products (e.g. flint) containing this active ingredient are approved.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g Entry on trifloxistrobin in the GESTIS substance database of the IFA , accessed on April 23, 2013(JavaScript required) .
↑ ^a ^b ^c ^d ^e FAO: TRIFLOXYSTROBIN (PDF; 1.8 MB)
↑ entry on trifloxistrobin; Methyl (E) -methoxyimino - {(E) -α- [1- (α, α, α-trifluoro-m-tolyl) ethylideneaminooxy] -o-tolyl} acetate 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 Datasheet Trifloxystrobin, PESTANAL at Sigma-Aldrich , accessed on May 19, 2017 ( PDF ).
↑ Ulrich Schirmer, Peter Jeschke, Matthias Witschel: Modern Crop Protection Compounds: Herbicides . John Wiley & Sons, 2012, ISBN 978-3-527-32965-6 , pp. 616 ( limited preview in Google Book search).
↑ infu.tu-dortmund.de: Environmental behavior of trifloxystrobin in soils from different geographical regions and the photolytic degradation in water
^ Horst Börner, Klaus Schlueter: Plant diseases and plant protection . Springer, 2009, ISBN 3-540-49068-X , pp. 495 ( limited preview in Google Book search).
↑ Directive 2003/68 / EC of the Commission of July 11, 2003 (PDF) amending Council Directive 91/414 / EEC to include the active substances trifloxystrobin, carfentrazone-ethyl, mesotrione, fenamidone and isoxaflutole.
↑ Regulation (EU) No. 823/2012 of the Commission of September 14, 2012. (PDF)
↑ Implementing Regulation (EU) 2018/1060 of the Commission of July 26, 2018 for the renewal of the approval for the active substance trifloxystrobin. (PDF)
↑ General Directorate Health and Food Safety of the European Commission: Entry on trifloxystrobin in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 4, 2020.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g Entry on trifloxistrobin in the GESTIS substance database of the IFA , accessed on April 23, 2013(JavaScript required) .

[FAO-2] FAO: TRIFLOXYSTROBIN (PDF; 1.8 MB)

[CLP_100.119.778-3] try on trifloxistrobin; Methyl (E) -methoxyimino - {(E) -α- [1- (α, α, α-trifluoro-m-tolyl) ethylideneaminooxy] -o-tolyl} acetate 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] Datasheet Trifloxystrobin, PESTANAL at Sigma-Aldrich , accessed on May 19, 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. 616 ( limited preview in Google Book search).

[infu.tu-dortmund.de-6] u.tu-dortmund.de: Environmental behavior of trifloxystrobin in soils from different geographical regions and the photolytic degradation in water

[Horst_Börner,_Klaus_Schlüter-7] Horst Börner, Klaus Schlueter: Plant diseases and plant protection . Springer, 2009, ISBN 3-540-49068-X , pp. 495 ( limited preview in Google Book search).

[8] Directive 2003/68 / EC of the Commission of July 11, 2003 (PDF) amending Council Directive 91/414 / EEC to include the active substances trifloxystrobin, carfentrazone-ethyl, mesotrione, fenamidone and isoxaflutole.

[9] Regulation (EU) No. 823/2012 of the Commission of September 14, 2012. (PDF)

[10] Implementing Regulation (EU) 2018/1060 of the Commission of July 26, 2018 for the renewal of the approval for the active substance trifloxystrobin. (PDF)

[PSM-11] General Directorate Health and Food Safety of the European Commission: Entry on trifloxystrobin in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 4, 2020.