Diclobutrazole

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Structural formula
Structural formula of diclobutrazole
1: 1 mixture of ( R ) -form (top) and ( S ) -form (bottom)
General
Surname Diclobutrazole
other names
  • α- tert -Butyl-β- (2,4-dichlorobenzyl) -1 H -1,2,4-triazole-1-ethanol
  • ( R * , R * ) - (+) - β - [(2,4-dichlorophenyl) methyl] -α- (1,1-dimethylethyl) -1 H -1,2,4-triazole-1-ethanol
  • (2 RS , 3 RS ) -1- (2,4-dichlorophenyl) -4,4-dimethyl-2- (1 H -1,2,4-triazol-1-yl) pentan-3-ol ( IUPAC )
  • Vigil
Molecular formula C 15 H 19 Cl 2 N 3 O
External identifiers / databases
CAS number 75736-33-3
EC number 620-436-0
ECHA InfoCard 100.149.227
PubChem 53309
Wikidata Q3026668
properties
Molar mass 328.24 g mol −1
Physical state

firmly

Melting point

148 ° C

solubility

practically insoluble in water (9 mg l −1 at 20 ° C)

safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
07 - Warning 09 - Dangerous for the environment

Caution

H and P phrases H: 319-411
P: 273-305 + 351 + 338
Toxicological data
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Diclobutrazole is a racemic mixture of two chemical compounds from the group of triazoles that is effective as a fungicide .

Extraction and presentation

Diclobutrazole can be obtained from 1,2,4-triazole . This reacts with bromopinacolone in the presence of sodium ethanolate . The resulting product reacts further with 2,4-dichlorobenzyl chloride , sodium hydride and sodium borohydride to form diclobutrazole.

Analytics

The reliable quantitative determination of diclobutrazole in different matrices is possible through the use of HPLC using a diode array detector after adequate sample preparation .

use

Diclobutrazole is used as a fungicide in grain and coffee growing. The compound acts by inhibiting the C14-demethylase in sterol synthesis .

Admission

The active ingredient diclobutrazole was approved in Germany from 1986 to 1996.

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

See also

Individual evidence

  1. ↑ a b Entry on diclobutrazole in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on July 31, 2014.
  2. ↑ a b data sheet diclobutrazol, PESTANAL at Sigma-Aldrich , accessed on May 27, 2014 ( PDF ).
  3. ↑ Entry on (2RS, 3RS) -1- (2,4-dichlorophenyl) -4,4-dimethyl-2- (1H-1,2,4-triazol-1yl) pentan-3-ol 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 .
  4. ↑ a b Entry on diclobutrazole in the GESTIS substance database of the IFA , accessed on July 31, 2014 (JavaScript required)
  5. ↑ Alanwood .
  6. ↑ a b Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 689 ( limited preview in Google Book search).
  7. ↑ C. Bicchi, C. Cordero, P. Rubiolo, A. Occelli: Simultaneous determination of six triazolic pesticide residues in apple and pear pulps by liquid chromatography with ultraviolet diode array detection. In: Journal of AOAC International . Volume 84, Number 5, 2001 Sep-Oct, pp. 1543-1550, ISSN  1060-3271 , PMID 11601474 .
  8. ↑ approval history of the BVL .
  9. ↑ General Directorate Health and Food Safety of the European Commission: Entry on diclobutrazole in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 26, 2016.