Triadimephone

Structural formula
Structural formula with undefined stereochemistry
General
Surname	Triadimephone
other names	( RS ) -1- (4-chlorophenoxy) -3,3-dimethyl-1- (1,2,4-triazol-1-yl) butanone (±) -1- (4-Chlorophenoxy) -3,3-dimethyl-1- (1,2,4-triazol-1-yl) -butanone DL -1- (4-chlorophenoxy) -3,3-dimethyl-1- (1,2,4-triazol-1-yl) butanone
Molecular formula	C 14 H 16 ClN 3 O 2
Brief description	colorless solid with a characteristic odor
External identifiers / databases
CAS number 43121-43-3 EC number 256-103-8 ECHA InfoCard 100.050.986 PubChem 39385 ChemSpider 36029 Wikidata Q2452254
properties
Molar mass	293.75 g mol −1
Physical state	firmly
density	1.22 g cm −3
Melting point	82 ° C
Vapor pressure	0.02 mPa (25 ° C)
solubility	practically insoluble in water (64 mg l −1 at 20 ° C) sparingly soluble in n -hexane easily soluble in 2-propanol, dichloromethane, toluene
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary Caution H and P phrases H: 302-317-410 P: 280-301 + 312 + 330
Toxicological data	363 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 .

Triadimefon is a 1: 1 mixture ( racemate ) of two stereoisomeric chemical compounds from the group of triazoles and conazoles .

Stereoisomerism

Triadimefon is chiral , so it contains a stereocenter . There are thus two stereoisomers, the ( R ) enantiomer and the ( S ) enantiomer. The 1: 1 mixture ( racemate ) of ( R ) - and ( S ) -enantiomer is called ( RS ) -Triadimefon or (±) -Triadimefon. If “Triadimefon” is mentioned in the scientific literature or in this article without further details, the racemate is meant.

Extraction and presentation

Triadimefon can be produced by dichlorination of pinacolone and subsequent substitution with sodium p -chlorophenolate and triazole .

The synthesis by reaction of bromopinacolone with the sodium salt of p -chlorophenol and reaction of the respective intermediate with bromine and 1,2,4-triazole is also possible .

properties

Triadimefon is a colorless solid with a characteristic odor, which is practically insoluble in water. It is moderately soluble in most organic solvents except aliphatics. Triadimenol is the main breakdown product . It is stable to hydrolysis over a wide pH range. The metabolism of Triadimefon is enantioselective , i.e. i.e., ( R ) and ( S ) enantiomers are metabolized at different rates.

use

Triadimefon is used as a fungicide . It is used in grain, coffee, fruit, grapes, tea, turf and vegetables and is approved in more than 70 countries. The effect is based on the influence of sterol biosynthesis (steroid demethylation) in the cell membranes.

Admission

Triadimefon was approved in the FRG between 1976 and 2003, in the GDR between 1980 and 1994.

In 2004, the EU Commission decided not to include Triadimefon in the list of permitted active ingredients in pesticides according to Directive 91/414 / EEC.

In Germany, Austria and Switzerland, no pesticides with this active ingredient are permitted.

Individual evidence

1. ↑ ^{a b c} Entry on Triadimefon in the Hazardous Substances Data Bank , accessed September 17, 2012.
2. ↑ ^{a b c d e f} Entry on Triadimefon in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .
3. ↑ ^{a b c} 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 .
4. ↑ Entry on 1- (4-chlorophenoxy) -3,3-dimethyl-1- (1,2,4-triazol-1-yl) butanone 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 .
5. ↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 722 (English, limited preview in Google Book search).
6. ↑ EPA: Reregistration Eligibility Decision for Triadimefon (PDF; 2.9 MB).
7. ↑ ^{a b} 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. 1090 (English, limited preview in Google Book Search).
8. ↑ AHB Deas, GA Carter, T. Clark, DR Clifford, CS James: The enantiomeric composition of triadimenol produced during metabolism of triadimefon by fungi: III. Relationship with sensitivity to triadimefon , Pesticide Biochemistry and Physiology 26, 1986, pp. 10-21.
9. ↑ 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 DE, 2010, ISBN 3-0348-0028-2 , pp. 27 ( limited preview in Google Book search).
10. ↑ Decision of the Commission of January 30, 2004 on the non-inclusion of certain active substances in Annex I of Council Directive 91/414 / EEC and the revocation of the authorizations for plant protection products with these active substances (2004/129 / EC)
11. ↑ General Directorate Health and Food Safety of the European Commission: Entry on Triadimefon in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved February 25, 2016.