Etaconazole

Structural formula
	Mixture of stereoisomers - structural formula without stereochemistry
General
Surname	Etaconazole
other names	1 - [(2 RS , 4 RS ; 2 RS , 4 SR ) -2- (2,4-dichlorophenyl) -4-ethyl-1,3-dioxolan-2-ylmethyl] -1 H -1,2,4 -triazole
Molecular formula	C 14 H 15 Cl 2 N 3 O 2
Brief description	colorless solid
External identifiers / databases
ECHA InfoCard	100.056.443
PubChem	91673
Wikidata	Q19279347
properties
Molar mass	328.19 g mol −1
Physical state	firmly
density	1.4 g cm −3
Melting point	75-93 ° C
solubility	practically insoluble in water (80 mg l −1 at 20 ° C); soluble in acetone, dichloromethane and methanol;
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 302
	P: no P-phrases
Toxicological data	1343 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 .

Etaconazole is a chemical compound belonging to the Conazole group .

Extraction and presentation

Etaconazole can be synthesized starting from a bromination of 2,4-dichloroacetophenone with bromine and subsequent dehydration of the ω-bromo-2,4-dichloroacetophenone formed using 1,2-butanediol and p- toluenesulfonic acid as a catalyst. This is followed by condensation of the 2- (2,4-dichlorophenyl) -2-bromomethyl-4-ethyl-1,3-dioxolane obtained with 1,2,4-triazole to give the end product.

properties

Etaconazole is a colorless solid that is practically insoluble in water. The fungicide consists of four stereoisomers.

use

Etaconazole has been used as a fungicide against powdery mildew on fruits and other crops. It was launched in 1979 but was later replaced by other fungicides. The effect is due to inhibition of sterol - biosynthesis .

Individual evidence

↑ ^a ^b ^c ^d Entry on Etaconazole in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on January 26, 2015.
↑ ^a ^b ^c ^d Datasheet Etaconazole, PESTANAL at Sigma-Aldrich , accessed on October 10, 2016 ( PDF ).
↑ ^a ^b ^c S. Gangolli, Royal Society of Chemistry (Great Britain): The Dictionary of Substances and Their Effects: D . Royal Society of Chemistry, 1999, ISBN 978-0-85404-818-2 , pp. 82 ( limited preview in Google Book search).
↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 978-0-8155-1853-2 , pp. 693 ( limited preview in Google Book search).
↑ ^a ^b P. Doyle, T. Fujita: Pesticide Chemistry: Human Welfare and Environment: Synthesis and Structure ... Elsevier, 2013, ISBN 978-1-4831-5086-4 , pp. 303 ( limited preview in Google Book search).

[ppdb-1] Entry on Etaconazole in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on January 26, 2015.

[Sigma-2] Datasheet Etaconazole, PESTANAL at Sigma-Aldrich , accessed on October 10, 2016 ( PDF ).

[S._Gangolli-3] S. Gangolli, Royal Society of Chemistry (Great Britain): The Dictionary of Substances and Their Effects: D . Royal Society of Chemistry, 1999, ISBN 978-0-85404-818-2 , pp. 82 ( limited preview in Google Book search).

[Thomas_A._Unger-4] Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 978-0-8155-1853-2 , pp. 693 ( limited preview in Google Book search).

[P._Doyle,_T._Fujita-5] P. Doyle, T. Fujita: Pesticide Chemistry: Human Welfare and Environment: Synthesis and Structure ... Elsevier, 2013, ISBN 978-1-4831-5086-4 , pp. 303 ( limited preview in Google Book search).