Triticonazole

Structural formula
	1: 1 mixture ( racemate ) of ( R ) -form (top) and ( S ) -form (bottom)
General
Surname	Triticonazole
other names	( E ) -5- (4-chlorobenzylidene) -2,2-dimethyl-1- (1 H -1,2,4-triazol-1-ylmethyl) cyclopentanol; ( RS ) - ( E ) -5- (4-chlorobenzylidene) -2,2-dimethyl-1- (1 H -1,2,4-triazol-1-methyl) cyclopentanol; (±) - ( E ) -5+ (4-Chlorbenzylidene) -2,2-dimethyl-1- (1 H -1,2,4-triazol-1-methyl) cyclopentanol;
Molecular formula	C 17 H 20 ClN 3 O
Brief description	white solid
External identifiers / databases
EC number	603-543-7
ECHA InfoCard	100.126.137
PubChem	6537961
ChemSpider	5020874
Wikidata	Q2366874
properties
Molar mass	317.82 g mol −1
Physical state	firmly
density	1.345 g cm −3
Melting point	139-140.5 ° C
solubility	practically insoluble in water (8 mg l −1 at 20 ° C); soluble in dichloromethane, acetone and ethyl acetate;
safety instructions
GHS hazard labeling from Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
H and P phrases	H: 411
	P: 273
Toxicological data	> 2000 mg kg −1 ( LD 50 , rat , oral ) ; > 2000 mg kg −1 ( LD 50 , rat , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Triticonazole is a chemical compound belonging to the triazole group . It is chiral and is used as a 1: 1 mixture of the mutually stereoisomeric structures.

Extraction and presentation

Triticonazole can be obtained by a multi-stage reaction starting from 2,2-dimethyl-pentenoic acid chloride with aluminum chloride , hydrogen , 4-chlorobenzaldehyde , trimethylsulfonium iodide , dimethylsulfoxide and 1,2,4-triazole .

properties

Triticonazole is a flammable white solid that is practically insoluble in water. The commercially available product is a racemate . So far nothing is known about the synthesis and biological properties of the individual enantiomers . After reaching the melting temperature, a weak decomposition begins, this becomes significant from a temperature of 180 ° C. The compound is stable to hydrolysis at pH 5, 7 and 9.

use

Triticonazole is used as an active ingredient in crop protection products. It is used as a fungicide in grain and maize, for example against Rhynchosporium and maize head brandy ( Sphacelotheca reiliana ).

Admission

The compound was approved for use as a fungicide in the European Union with effect from February 1, 2007. In Germany, Austria and Switzerland, plant protection products (e.g. Real and Rubin Top) with this active ingredient are approved. It has been approved in Germany since 1971.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry for CAS no. 131983-72-7 in the GESTIS substance database of the IFA , accessed on September 17, 2012(JavaScript required) .
↑ ^a ^b EU: Review report for the active substance triticonazole finalized in the Standing Committee on the Food Chain and Animal Health at its meeting on 27 January 2006 in view of the inclusion of triticonazole in Annex I of Directive 91/414 / EEC (PDF File; 99 kB), March 12, 2010
↑ Entry on (RS) - (E) -5- (4-chlorobenzylidene) -2,2-dimethyl-1- (1H-1,2,4-triazol-1-methyl) cyclopentanol 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 .
↑ ^a ^b ^c Data sheet Triticonazole from Sigma-Aldrich , accessed on May 20, 2017 ( PDF ).
↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1401-8 , pp. 727 ( limited preview in Google Book search).
↑ Wolfgang Krämer, Ulrich Schirmer, Peter Jeschke, Matthias Witschel: Modern Crop Protection Compounds . John Wiley & Sons, 2012, ISBN 978-3-527-32965-6 , pp. 780 ff . ( limited preview in Google Book search).
↑ Directive 2006/39 / EC of the Commission of April 12, 2006 amending Directive 91/414 / EEC of the Council to include the active substances clodinafop, pirimicarb, rimsulfuron, tolclofos-methyl and triticonazole (PDF)
↑ General Directorate Health and Food Safety of the European Commission: Entry on triticonazole in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 13, 2016.
↑ 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. 28 ( limited preview in Google Book search).

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry for CAS no. 131983-72-7 in the GESTIS substance database of the IFA , accessed on September 17, 2012(JavaScript required) .

[EU-2] EU: Review report for the active substance triticonazole finalized in the Standing Committee on the Food Chain and Animal Health at its meeting on 27 January 2006 in view of the inclusion of triticonazole in Annex I of Directive 91/414 / EEC (PDF File; 99 kB), March 12, 2010

[CLP_100.126.137-3] Entry on (RS) - (E) -5- (4-chlorobenzylidene) -2,2-dimethyl-1- (1H-1,2,4-triazol-1-methyl) cyclopentanol 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 .

[Sigma-4] Data sheet Triticonazole from Sigma-Aldrich , accessed on May 20, 2017 ( PDF ).

[Thomas_A._Unger-5] Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1401-8 , pp. 727 ( limited preview in Google Book search).

[Wolfgang_Krämer,_Ulrich_Schirmer,_Peter_Jeschke,_Matthias_Witschel-6] Wolfgang Krämer, Ulrich Schirmer, Peter Jeschke, Matthias Witschel: Modern Crop Protection Compounds . John Wiley & Sons, 2012, ISBN 978-3-527-32965-6 , pp. 780 ff . ( limited preview in Google Book search).

[7] Directive 2006/39 / EC of the Commission of April 12, 2006 amending Directive 91/414 / EEC of the Council to include the active substances clodinafop, pirimicarb, rimsulfuron, tolclofos-methyl and triticonazole (PDF)

[PSM-8] General Directorate Health and Food Safety of the European Commission: Entry on triticonazole in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 13, 2016.

[Peter_Brandt-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. 28 ( limited preview in Google Book search).