Simeconazole

Structural formula
Structural formula without stereochemistry
General
Surname	Simeconazole
other names	α- (4-Fluorophenyl) -α- (trimethylsilylmethyl) -1 H -1,2,4-triazole-1-ethanol ( RS ) -2- (4-fluorophenyl) -1- (1 H -1,2,4-triazol-1-yl) -3- (trimethylsilyl) propan-2-ol (±) -2- (4-fluorophenyl) -1- (1 H -1,2,4-triazol-1-yl) -3- (trimethylsilyl) propan-2-ol Sipconazole
Molecular formula	C 14 H 20 FN 3 OSi
Brief description	white crystals
External identifiers / databases
CAS number 149508-90-7 (racemate) 168125-52-8 [( S ) form] 168125-48-2 [( R ) -form] EC number 604-694-1 ECHA InfoCard 100.110.630 PubChem 10085783 ChemSpider 8261320 Wikidata Q18923169
properties
Molar mass	293.41 g mol −1
Physical state	firmly
Melting point	118.5-120.5 ° C
solubility	practically insoluble in water (57.5 mg l −1 at 20 ° C)
safety instructions
GHS labeling of hazardous substances Caution H and P phrases H: 302 P: no P-phrases
Toxicological data	648 mg kg −1 ( LD 50 ,  rat ,  oral , mean ♂ / ♀)
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Simeconazole is a chemical compound from the group of triazoles and conazoles and a fungicide introduced by Sankyo in 2001 . It is chiral and is used as a 1: 1 mixture of the mutually enantiomeric ( R ) form and the ( S ) form.

Extraction and presentation

Simeconazole can be obtained from α-chloro-4-fluoroacetophenone by reaction with 1,2,4-triazole sodium and addition of trimethylsilylmethylmagnesium chloride.

Stereochemistry

There are up to 2 ⁿ stereoisomers of chemical compounds with a stereocenter . Here n is the number of stereocenters. Accordingly, there are two stereoisomers of simeconazole, which have also been experimentally confirmed and approved:

Enantiomers of simeconazole
CAS number: 168125-52-8	CAS number: 168125-48-2

use

Simeconazole is used as a systemic broad spectrum fungicide in cereals, especially rice.

Admission

No plant protection products containing this active ingredient are permitted in the EU or Switzerland .

Individual evidence

1. ↑ ^{a b c d} Entry on simeconazole. In: Römpp Online . Georg Thieme Verlag, accessed on January 21, 2015.
2. ↑ ^{a b} Data sheet Simeconazole from Sigma-Aldrich , accessed on May 22, 2017 ( PDF ).
3. ↑ ^{a b} Wolfgang Krämer, Ulrich Schirmer, Peter Jeschke, Matthias Witschel: Modern Crop Protection Compounds: Herbicides, Volume 1 . Wiley-VCH, 2011, ISBN 978-3-527-32965-6 , pp. 790 ( limited preview in Google Book search).
4. ↑ Paula Y. Bruice: Organic Chemistry: Study compact . Pearson Studium, Munich 2011, ISBN 978-3-86894-102-9 , p. 205.
5. ↑ Elim M. Ulrich, Candice M. Morrison, Michael M. Goldsmith, William T. Foremann: Chiral Pesticides: Identification, Description, and Environmental Implications . In: Reviews of Environmental Contaminations and Toxicology. Springer 2012, Boston, Volume 217, pp. 1–74, DOI: 10.1007 / 978-1-4014-2329-4_1 , see p. 11.
6. ↑ Mikio Tsuda, Hiroyuki Itoh, Shigehiro Kato: Evaluation of the systemic activity of simeconazole in comparison with that of other DMI fungicides . In: Pest Management Science . tape 60 , no. 9 , September 2004, p. 875-880 , doi : 10.1002 / ps.907 ( PDF ).
7. ^ Directorate-General for Health and Food Safety of the European Commission: Entry on Simeconazole in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 27, 2016.