Propiconazole

Structural formula
Structural formula without stereochemistry
General
Surname	Propiconazole
other names	(±) -1 - {[2- (2,4-dichlorophenyl) -4-propyl-1,3-dioxolan-2-yl] methyl} - H -1,2,4-triazole ( IUPAC )
Molecular formula	C 15 H 17 Cl 2 N 3 O 2
Brief description	clear, light to dark yellow, highly viscous liquid with a faint odor
External identifiers / databases
CAS number 60207-90-1 (mixture of isomers) 116498-43-2 [( S , R ) -propiconazole] 116498-44-3 [( R , S ) -propiconazole] 116498-45-4 [( R , R ) -propiconazole] 116498-46-5 [( S , S ) -propiconazole] EC number 262-104-4 ECHA InfoCard 100.056.441 PubChem 43234 ChemSpider 39402 Wikidata Q414357
properties
Molar mass	342.22 g mol −1
Physical state	liquid
density	1.29 g cm −3
Melting point	−23 ° C
boiling point	180 ° C at 13 Pa
Vapor pressure	0.056 mPa
solubility	practically insoluble in water (100 mg m −3 ) bad in hexane soluble in methanol , acetone , diethyl ether , chloroform and benzene
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary danger H and P phrases H: 302-317-360D-410 P: 273-280-301 + 312 + 330-302 + 352-304 + 340 + 310
Toxicological data	1517 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 .

Propiconazole belongs to the group of triazoles and is a clear, yellowish, highly viscous liquid with a faint odor. The mixture of four stereoisomers is used as a fungicide .

Stereochemistry

Propiconazole contains two stereocenters and thus consists of four stereoisomers . It is a four-component mixture of ( S , S ) -, ( R , R ) -, ( S , R ) - and the ( R , S ) -form:

Propiconazole stereoisomers
( S , S ) -Propiconazole CAS number: 116498-46-5	( R , R ) -Propiconazole CAS number: 116498-45-4
( S , R ) -Propiconazole CAS number: 116498-43-2	( R , S ) -Propiconazole CAS number: 116498-44-3

history

Propiconazole was discovered by Janssen Pharmaceutica in 1979 and later developed by Ciba-Geigy .

use

Propiconazole is used as a fungicide. For example, as a wood preservative and for mushrooms, corn, peanuts, almonds, millet, oats, pecans , apricots, peaches, nectarines, plums and prunes. Approvals as pesticides existed in Germany, Austria and Switzerland. The main area of ​​application here was grain cultivation. However, the EEA member states must revoke the authorizations for plant protection products containing propiconazole as an active ingredient by June 19, 2019 at the latest. A use-by period of a maximum of nine months is granted. In Switzerland, plant protection products with the active ingredient propiconazole are still approved.

Web links

• Applications (English) (PDF file; 100 kB)

Individual evidence

1. ↑ ^{a b c d e f} Entry on propiconazole in the GESTIS substance database of the IFA , accessed on January 14, 2030(JavaScript required) .
2. ↑ 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 .
3. ↑ ^{a b c} data sheet Propiconazole at Extension Toxicology Network (English).
4. ↑ Entry on 1 - [[2- (2,4-dichlorophenyl) -4-propyl-1,3-dioxolan-2-yl] methyl] -1H-1,2,4-triazole in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on November 18, 2019. Manufacturers or distributors can expand the harmonized classification and labeling .
5. ↑ Data propiconazole at Sigma-Aldrich , accessed on 14 January 2020 ( PDF ).
6. ^ Entry on propiconazole in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on January 12, 2018.
7. ↑ ^{a b} entry on propiconazole. In: Römpp Online . Georg Thieme Verlag, accessed on January 11, 2015.
8. ↑ L. Toribio, MJ del Nozal, JL Bernal, JJ Jeménez and C. Alonso, J. Chromatography A 2004, 1046 , 249-253.
9. ↑ ^{a b} Directorate-General for Health and Food Safety of the European Commission: Entry on propiconazole in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on December 6, 2019.
10. ↑ Implementing Regulation (EU) 2018/1865 of the Commission of November 28, 2018 on the non-renewal of the approval for the active substance propiconazole according to Regulation (EC) No. 1107/2009 of the European Parliament and of the Council on the placing of plant protection products on the market and amending the Commission Implementing Regulation (EU) No. 540/2011