Prothioconazole

Structural formula
	Simplified structural formula without stereochemistry
General
Surname	Prothioconazole
other names	( RS ) -2- [2- (1-chlorocyclopropyl) -3- (2-chlorophenyl) -2-hydroxypropyl] -1,2-dihydro-3 H -1,2,4-triazole-3-thione; (±) -2- [2- (1-chlorocyclopropyl) -3- (2-chlorophenyl) -2-hydroxypropyl] -1,2-dihydro-3 H -1,2,4-triazole-3-thione;
Molecular formula	C 14 H 15 Cl 2 N 3 OS
Brief description	white odorless solid
External identifiers / databases
EC number	605-841-2
ECHA InfoCard	100.114.615
PubChem	6451142
ChemSpider	4953623
Wikidata	Q10816580
properties
Molar mass	344.26 g mol −1
Physical state	firmly
density	1.36 g cm −3
Melting point	141.8 ° C
boiling point	> 487 ° C
Vapor pressure	0.4 μPa (25 ° C)
solubility	practically insoluble in water (300 mg l −1 at 20 ° C); soluble in acetone and ethyl acetate;
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 410
	P: 273-501
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Prothioconazole is a mixture of two isomeric chemical compounds from the group of triazoles , more precisely the triazolinethiones .

Extraction and presentation

Prothioconazole can be obtained by reacting p -chlorobenzyl chloride with chloromethyl-1-chloro-cyclopropyl ketone and 1,2,4-triazole and reacting the intermediate product with n -butyllithium and elemental sulfur (S ₈ ).

properties

Prothioconazole is a white, odorless solid that is practically insoluble in water. The technical product is a 1: 1 mixture of the two enantiomers .

use

Prothioconazole is used as a fungicide . The compound was brought onto the market by Bayer in 2002 , was approved in 2004 and works by inhibiting ergosterol biosynthesis in cell membranes.

Admission

With effect from August 1, 2008, prothioconazole was included in Annex I of Directive 91/414 / EEC and is therefore an active ingredient in plant protection products permitted for use as a fungicide in the European Union .

In many EU countries, including Germany and Austria, as well as Switzerland, plant protection products (e.g. the EfA stain ) are approved with this active ingredient.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f data sheet prothioconazole, PESTANAL at Sigma-Aldrich , accessed on May 19, 2017 ( PDF ).
↑ ^a ^b ^c ^d ^e F. Müller, P. Ackermann, P. Margot: Fungicides, Agricultural, 2. Individual Fungicides . In: Ullmann's Encyclopedia of Technical Chemistry . Wiley-VCH, Weinheim 2012, doi : 10.1002 / 14356007.o12_o06 .
↑ ^a ^b BVL: prothioconazole
^ ^A ^b Ulrich Schirmer, Peter Jeschke, Matthias Witschel: Modern Crop Protection Compounds: Herbicides . John Wiley & Sons, 2012, ISBN 978-3-527-32965-6 , pp. 791 ff . (English, limited preview in Google Book Search).
↑ 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, 2010, ISBN 3-0348-0029-0 , pp. 24 ( limited preview in Google Book search).
^ Horst Börner, Klaus Schlueter: Plant diseases and plant protection . Springer, 2009, ISBN 3-540-49068-X , pp. 496 ( limited preview in Google Book search).
↑ Commission Directive 2008/44 / EC of April 4, 2008 amending Council Directive 91/414 / EEC to include the active substances benthiavalicarb, boscalid, carvone, fluoxastrobin, Paecilomyces lilacinus and prothioconazole
↑ General Directorate Health and Food Safety of the European Commission: Entry on prothioconazole in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 23, 2016.

[Sigma-1] ↑ ^a ^b ^c ^d ^e ^f data sheet prothioconazole, PESTANAL at Sigma-Aldrich , accessed on May 19, 2017 ( PDF ).

[UllmannTC-2] F. Müller, P. Ackermann, P. Margot: Fungicides, Agricultural, 2. Individual Fungicides . In: Ullmann's Encyclopedia of Technical Chemistry . Wiley-VCH, Weinheim 2012, doi : 10.1002 / 14356007.o12_o06 .

[BVL-3] BVL: prothioconazole

[Ulrich_Schirmer,_Peter_Jeschke,_Matthias_Witschel-4] A ^b Ulrich Schirmer, Peter Jeschke, Matthias Witschel: Modern Crop Protection Compounds: Herbicides . John Wiley & Sons, 2012, ISBN 978-3-527-32965-6 , pp. 791 ff . (English, limited preview in Google Book Search).

[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, 2010, ISBN 3-0348-0029-0 , pp. 24 ( limited preview in Google Book search).

[Horst_Börner,_Klaus_Schlüter-6] Horst Börner, Klaus Schlueter: Plant diseases and plant protection . Springer, 2009, ISBN 3-540-49068-X , pp. 496 ( limited preview in Google Book search).

[7] Commission Directive 2008/44 / EC of April 4, 2008 amending Council Directive 91/414 / EEC to include the active substances benthiavalicarb, boscalid, carvone, fluoxastrobin, Paecilomyces lilacinus and prothioconazole

[PSM-8] General Directorate Health and Food Safety of the European Commission: Entry on prothioconazole in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 23, 2016.