Triadimenol

Structural formula
Structural formula without stereochemistry
General
Surname	Triadimenol
other names	α- tert -Butyl-β- (4-chlorophenoxy) -1 H -1,2,4-triazole-1-ethanol
Molecular formula	C 14 H 18 ClN 3 O 2
Brief description	white to gray solid with a phenolic odor
External identifiers / databases
CAS number 55219-65-3 (unspecified stereochemistry) 89482-17-7 (racemic diastereoisomer A) 82200-72-4 (racemic diastereoisomer B) 89497-66-5 [(α R , β S ) stereoisomer] 89497-63-2 [(α S , β R ) stereoisomer] 89497-64-3 [(α R , β R ) stereoisomer] 89497-65-4 [(α S , β S ) stereoisomer] EC number 259-537-6 ECHA InfoCard 100.054.106 PubChem 41368 ChemSpider 37749 Wikidata Q15632882
properties
Molar mass	295.77 g mol −1
Physical state	firmly
density	1.24 g cm −3 [racemic A diastereomer - threo form ( R , S ) + ( S , R )] 1.30 g cm −3 [racemic B diastereomer - erythro form ( R , R ) + ( S , S )]
Melting point	138.2 ° C (racemic A diastereomer) 133.5 ° C (racemic B diastereomer)
solubility	practically insoluble in water (62 or 33 mg l −1 at 20 ° C) soluble in acetone, 2-propanol, dichloromethane, ethyl acetate and dimethyl sulfoxide
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary danger H and P phrases H: 302-360-362-411 P: 261-301 + 312 + 330
Toxicological data	689 - 752 mg kg −1 ( LD 50 ,  rat ,  oral ) > 5000 mg kg −1 ( LD 50 ,  rat ,  transdermal ) > 1 mg l −1 ( LC 50 ,  rat ,  inh. , 4 h) 17.4 mg l −1 ( LC 50 ,  fish , 96 h , median value)
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Triadimenol is a mixture of four isomeric chemical compounds from the group of conazoles and triazoles .

Extraction and presentation

Triadimenol can be produced by a Meerwein-Ponndorf-Verley reduction of Triadimefon with aluminum isopropanolate .

properties

Triadimenol is a flammable white to gray solid with a phenol-like odor that is practically insoluble in water. It has a flash point of 100 ° C and decomposes when heated above 150 ° C. Triadimenol is stable to hydrolysis at pH values of 4, 7 and 9 and is slightly subject to photolysis .

Stereochemistry

Triadimenol contains two stereocenters in the α-position and the β-position:

There are four stereoisomers in total . The technical product consists of 70 to 85% of the racemic diastereoisomer A [(α R , β S ) + (α S , β R )], the diastereoisomer B [(α R , β R ) + (α S , β S )], however, is between 15 and 30%:

Triadimenol stereoisomers
(α R , β S ) stereoisomer	(α S , β R ) stereoisomer
(α R , β R ) stereoisomer	(α S , β S ) stereoisomer

use

Triadimenol is a systemic fungicide with a broad spectrum of activity. It inhibits the ergosterol - and gibberellin - biosynthesis and thus the rate of cell division. The compound was launched in 1978.

Admission

In the European Union, triadimenol has been used as a fungicide in crop protection products since September 2009. Since no application for renewal of the active substance approval was submitted, the EU approval for triadimenol as an active substance in plant protection products, in accordance with Implementing Regulation (EU) No. 540/2011, ended on August 31, 2019 due to the passage of time. In Germany, according to the Plant Protection Act, there is a sale period until February 29, 2020 and a use-by period until February 28, 2021. In Switzerland, the use-by period for the only pesticide available with this active ingredient ends on October 31, 2020. In ten EU member states remains Triadimenol approved under certain conditions. In addition, the active ingredient manufactured by Bayer is also sold on the Brazilian and South African markets.

Individual evidence

1. ↑ ^{a b c d e f g h i j k l} Entry on Triadimenol in the GESTIS substance database of the IFA , accessed on = 31. December 2019(JavaScript required) .
2. ↑ ^{a b c} FAO: FAO SPECIFICATIONS AND EVALUATIONS FOR AGRICULTURAL PESTICIDES - Triadimenol (PDF; 524 kB)
3. ↑ Entry on α-tert-butyl-β- (4-chlorophenoxy) -1H-1,2,4-triazole-1-ethanol in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on December 31, 2019. Manufacturer or distributors can expand the harmonized classification and labeling .
4. ↑ Triadimenol data sheet at Sigma-Aldrich , accessed on = 31. December 2019 ( PDF ).
5. ^ Entry on Triadimenol in the Hazardous Substances Data Bank , accessed April 12, 2013.
6. ↑ ^{a b} Directorate-General for Health and Food Safety of the European Commission: Entry on Triadimenol in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland and Germany ; accessed on April 25, 2020.
7. ^ Horst Börner, Klaus Schlueter: Plant diseases and plant protection . Springer, 2009, ISBN 3-540-49068-X , pp. 496 ( limited preview in Google Book search).
8. ↑ Commission Directive 2008/125 / EC of December 19, 2008 (PDF) amending Council Directive 91/414 / EEC to include aluminum phosphide, calcium phosphide, magnesium phosphide, cymoxanil, dodemorph, 2,5-dichlorobenzoic acid methyl ester, metamitron, sulcotrione , Tebuconazole and triadimenol as active ingredients.
9. ↑ Federal Office of Consumer Protection and Food Safety: revocation of the authorization of plant protection products containing triadimenol August 31, 2019. In: bvl.bund.de . May 8, 2019, accessed May 10, 2019 . 
10. Jump up ↑ Benjamin Luig, Fran Paula de Castro and Alan Tygel (both Campanha Permanente Contra os Agrotóxicos e Pela Vida), Lena Luig (INKOTA network), Simphiwe Dada (Khanyisa), Sarah Schneider (MISEREOR) and Jan Urhahn (Rosa-Luxemburg- Foundation): Dangerous pesticides. (PDF; 2.4 MB) from Bayer and BASF - a global business with double standards. Rosa Luxemburg Foundation , INKOTA network , Episcopal Aid Organization Misereor u. a., April 2020, accessed on April 25, 2020 .