Tetraconazole

Structural formula
	1: 1 mixture of ( R ) -form (left) ; and ( S ) -form (right)
General
Surname	Tetraconazole
other names	( RS ) -2- (2,4-dichlorophenyl) -3- (1 H -1,2,4-triazol-1-yl) propyl-1,1,2,2-tetrafluoroethyl ether; (±) -2- (2,4-dichlorophenyl) -3- (1 H -1,2,4-triazol-1-yl) propyl-1,1,2,2-tetrafluoroethyl ether;
Molecular formula	C 13 H 11 Cl 2 F 4 N 3 O
Brief description	colorless viscous liquid
External identifiers / databases
EC number	407-760-6
ECHA InfoCard	100.100.923
Wikidata	Q2406717
properties
Molar mass	372.15 g mol −1
Physical state	liquid
density	1.432 g cm −3
Melting point	6 ° C
boiling point	240 ° C (decomposition)
Vapor pressure	negligible
solubility	very sparingly soluble in water (150 mg l −1 at 20 ° C); soluble in xylene, acetone and ethyl acetate;
safety instructions
H and P phrases	H: 302 + 332-411
	P: 273
Toxicological data	1031 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Tetraconazole is a 1: 1 mixture of two enantiomeric chemical compounds from the group of triazoles and conazoles .

Extraction and presentation

Tetraconazole can be obtained by nucleophilic substitution of the mesyl group of methyl 2- (2,4-dichlorophenyl) -3-mesylpropanoate with triazole, followed by reduction of the ester to the alcohol by lithium aluminum hydride and alkylation of the hydroxy group with tetrafluoroethylene .

properties

Tetraconazole is a colorless, oily, non-volatile liquid that is very sparingly soluble in water. When heated above 240 ° C the compound decomposes. It is a racemate of the isomers.

use

Tetraconazole is used as a fungicide against powdery mildew , brown rust , Septoria and Rhyncosporium in grain and scab in apples. The effect is based on blocking the ergosterol biosynthesis in the cell membranes of the fungi. It was brought onto the market by the Italian company Ricerca and is now distributed by the Isagro company. The more active isomer is the ( R ) - (+) - enantiomer .

Admission

The active ingredient tetraconazole was licensed under certain conditions in the European Union for use as a fungicide in arable farming. The application restriction to arable farming and the requirements were lifted in 2010.

In Switzerland none, in Austria and Germany, pesticides (e.g. Emerald) with this active ingredient are permitted.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on tetraconazole in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
↑ ^a ^b Entry on Tetraconazole in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on July 31, 2013.
↑ Entry on (+/-) 2- (2,4-dichlorophenyl) -3- (1H-1,2,4-triazole-1-yl) propyl-1,1,2,2-tetrafluoroethyl ether 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 Wolfgang Krämer, Ulrich Schirmer, Peter Jeschke, Matthias Witschel: Modern Crop Protection Compounds . John Wiley & Sons, 2012, ISBN 978-3-527-32965-6 , pp. 776 ( limited preview in Google Book search).
↑ EU: Review report for the active substance tetraconazole (PDF; 43 kB)
↑ Terry R Roberts, David H Hutson, Philip W Lee, Peter H Nicholls: Metabolic Pathways of Agrochemicals: Part 2: Insecticides and Fungicides . Royal Society of Chemistry, 1999, ISBN 0-85404-499-X , pp. 1088 ( limited preview in Google Book Search).
↑ Reasoned opinion on the modification of the existing MRL for tetraconazole in rape seed. In: EFSA Journal. 10, 2012, doi : 10.2903 / j.efsa.2012.2842 .
↑ Council Directive 2009/82 / EC of July 13, 2009 amending Directive 91/414 / EEC to include the active substance tetraconazole (PDF)
↑ Commission Directive 2010/82 / EU of 29 November 2010 amending Council Directive 91/414 / EEC as regards an extension of the use of the active substance tetraconazole (PDF)

^ Directorate-General for Health and Food Safety of the European Commission: Entry on Tetraconazole in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 12, 2016.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on tetraconazole in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .

[PPDB-2] Entry on Tetraconazole in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on July 31, 2013.

[CLP_100.100.923-3] Entry on (+/-) 2- (2,4-dichlorophenyl) -3- (1H-1,2,4-triazole-1-yl) propyl-1,1,2,2-tetrafluoroethyl ether 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 .

[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. 776 ( limited preview in Google Book search).

[5] EU: Review report for the active substance tetraconazole (PDF; 43 kB)

[Terry_R_Roberts,David_H_Hutson,Philip_W_Lee,Peter_H_Nicholls-6] Terry R Roberts, David H Hutson, Philip W Lee, Peter H Nicholls: Metabolic Pathways of Agrochemicals: Part 2: Insecticides and Fungicides . Royal Society of Chemistry, 1999, ISBN 0-85404-499-X , pp. 1088 ( limited preview in Google Book Search).

[7] Reasoned opinion on the modification of the existing MRL for tetraconazole in rape seed. In: EFSA Journal. 10, 2012, doi : 10.2903 / j.efsa.2012.2842 .

[8] Council Directive 2009/82 / EC of July 13, 2009 amending Directive 91/414 / EEC to include the active substance tetraconazole (PDF)

[9] Commission Directive 2010/82 / EU of 29 November 2010 amending Council Directive 91/414 / EEC as regards an extension of the use of the active substance tetraconazole (PDF)

[PSM-10] Directorate-General for Health and Food Safety of the European Commission: Entry on Tetraconazole in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 12, 2016.