Tebuconazole

Structural formula
	1: 1 mixture ( racemate ) of ( R ) -form (top) and ( S ) -form (bottom)
General
Surname	Tebuconazole
other names	( RS ) -1- tert -Butyl-1- (4-chlorophenethyl) -2- (1 H -1,2,4-triazol-1-yl) ethanol; (±) -1- tert -Butyl-1- (4-chlorophenethyl) -2- (1 H -1,2,4-triazol-1-yl) ethanol; ( RS ) -1- (4-chlorophenyl) -4,4-dimethyl-3- (1,2,4-triazol-1-ylmethyl) -pentan-3-ol; (±) -1- (4-Chlorophenyl) -4,4-dimethyl-3- (1,2,4-triazol-1-ylmethyl) -pentan-3-ol;
Molecular formula	C 16 H 22 ClN 3 O
Brief description	colorless and odorless solid
External identifiers / databases
EC number	403-640-2
ECHA InfoCard	100.100.535
PubChem	86102
ChemSpider	77680
Wikidata	Q2697579
properties
Molar mass	307.82 g mol −1
Physical state	firmly
density	1.25 g cm −3
Melting point	102 ° C
boiling point	165 ° C (decomposition)
Vapor pressure	3.9 µPa (25 ° C)
solubility	practically insoluble in water (29 mg l −1 at 20 ° C); very soluble in organic solvents;
safety instructions
H and P phrases	H: 302-361d-410
	P: 273-281
Toxicological data	3350 mg kg −1 ( LD 50 , rat , oral ) ; 4488 mg kg −1 ( LD 50 , chicken , oral ) ; > 5000 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 .

Tebuconazole is a mixture of two enantiomeric chemical compounds from the group of triazoles .

Extraction and presentation

Tebuconazole can be obtained by ring opening of 2- tert -butyl-2- (4-chlorophenethyl) oxirane with 1,2,4-triazole in the presence of a base.

Stereochemistry

Since tebuconazole contains a stereocenter , there are two enantiomers of this active ingredient. Technical tebuconazole is used as a 1: 1 mixture ( racemate ) of the ( R ) and ( S ) form.

properties

Tebuconazole is a flammable, colorless and odorless solid that is practically insoluble in water. It is stable to hydrolysis at pH values of 5, 7 and 9.

use

Tebuconazole is used as a fungicide . The effect is based on the substance's intervention in the metabolism of the fungal cells. The compound was launched in 1988.

Tebuconazole is also added to wood preservatives as a fungicidal active ingredient.

Admission

In the European Union, plant protection products containing tebuconazole have been permitted for use as fungicides since September 2009.

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

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on tebuconazole in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
↑ ^a ^b ^c ^d ^e ^f BAUA: Page no longer available , search in web archives: Directive 98/8 / EC concerning the placing of biocidal products on the market - Tebuconazol , November 29, 2007.@1@ 2Template: Dead Link / circa.europa.eu

↑ Müller, F .; Ackermann, P .; Margot, P .: Fungicides, Agricultural, 2. Individual Fungicides in Ullmanns Enzyklopädie der Technischen Chemie , 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, doi : 10.1002 / 14356007.o12_o06 .

↑ Entry on Tebuconazole (ISO); 1- (4-Chlorophenyl) -4,4-dimethyl-3- (1,2,4-triazol-1-ylmethyl) pentan-3-ol in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on 24. January 2017. Manufacturers or distributors can extend the harmonized classification and labeling .

↑ ^a ^b Tebuconazole data sheet from Sigma-Aldrich , accessed on May 15, 2017 ( PDF ).

^ Entry on tebuconazole in the Hazardous Substances Data Bank , accessed April 8, 2013.

↑ Thomas A. Unger: Pesticide synthesis handbook . 1996, ISBN 978-0-8155-1401-5 , pp. 720 ( 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).

↑ Directive 2008/125 / EC of the Commission of December 19, 2008 amending Directive 91/414 / EEC of the Council to include aluminum phosphide, calcium phosphide, magnesium phosphide, cymoxanil, dodemorph, 2,5-dichlorobenzoate, metamitron, sulcotrione, tebuconazole and Triadimenol as active ingredients (PDF) .

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

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

[Baua-2] ↑ ^a ^b ^c ^d ^e ^f BAUA: Page no longer available , search in web archives: Directive 98/8 / EC concerning the placing of biocidal products on the market - Tebuconazol , November 29, 2007.@1@ 2Template: Dead Link / circa.europa.eu

[UllmannTC-3] Müller, F .; Ackermann, P .; Margot, P .: Fungicides, Agricultural, 2. Individual Fungicides in Ullmanns Enzyklopädie der Technischen Chemie , 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, doi : 10.1002 / 14356007.o12_o06 .

[CLP_100.100.535-4] Entry on Tebuconazole (ISO); 1- (4-Chlorophenyl) -4,4-dimethyl-3- (1,2,4-triazol-1-ylmethyl) pentan-3-ol in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on 24. January 2017. Manufacturers or distributors can extend the harmonized classification and labeling .

[Sigma-5] Tebuconazole data sheet from Sigma-Aldrich , accessed on May 15, 2017 ( PDF ).

[HSDB-6] Entry on tebuconazole in the Hazardous Substances Data Bank , accessed April 8, 2013.

[Unger-7] Thomas A. Unger: Pesticide synthesis handbook . 1996, ISBN 978-0-8155-1401-5 , pp. 720 ( limited preview in Google Book Search).

[Horst_Börner,_Klaus_Schlüter-8] Horst Börner, Klaus Schlueter: Plant diseases and plant protection . Springer, 2009, ISBN 3-540-49068-X , pp. 496 ( limited preview in Google Book search).

[9] Directive 2008/125 / EC of the Commission of December 19, 2008 amending Directive 91/414 / EEC of the Council to include aluminum phosphide, calcium phosphide, magnesium phosphide, cymoxanil, dodemorph, 2,5-dichlorobenzoate, metamitron, sulcotrione, tebuconazole and Triadimenol as active ingredients (PDF) .

[PSM-10] General Directorate Health and Food Safety of the European Commission: Entry on Tebuconazole in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 23, 2016.