Penconazole
Structural formula | ||||||||||||||||
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Structural formula without stereochemistry | ||||||||||||||||
General | ||||||||||||||||
Surname | Penconazole | |||||||||||||||
other names |
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Molecular formula | C 13 H 15 Cl 2 N 3 | |||||||||||||||
Brief description |
white solid |
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External identifiers / databases | ||||||||||||||||
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properties | ||||||||||||||||
Molar mass | 284.18 g mol −1 | |||||||||||||||
Physical state |
firmly |
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density |
1.28 g cm −3 |
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Melting point |
60 ° C |
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Vapor pressure |
3.66 10 −4 Pa (25 ° C) |
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solubility |
practically insoluble in water (73 mg l −1 at 20 ° C) |
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safety instructions | ||||||||||||||||
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Toxicological data | ||||||||||||||||
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . |
Penconazole is a chemical compound from the triazole group . It is chiral and is used as a 1: 1 mixture of the mutually enantiomeric ( R ) form and the ( S ) form. It has been marketed by Ciba-Geigy as a pesticide ( fungicide ) since 1986 .
Extraction and presentation
Penconazole can be obtained from 2,4-dichlorobenzyl bromide. This reacts with potassium cyanate to form 2,4-dichlorophenylacetonitrile . Further reactions with sulfuric acid , 1-bromopropane , sodium borohydride , methanesulfonyl chloride and 1,2,4-triazole finally produce the end product.
Stereochemistry
Penconazole contains a stereocenter and consists of two enantiomers . This is a racemate , i.e. a 1: 1 mixture of ( R ) - and ( S ) -form:
Enantiomers of penconazole | |
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( S ) -penconazole |
( R ) -penconazole |
use
Penconazole is used as a systemic azole fungicide with a protective and curative effect against powdery mildew in viticulture, pumpkin, pome fruit, ornamentals and vegetables.
Admission
In a number of EU countries, including Germany and Austria, as well as Switzerland, plant protection products containing this active ingredient are approved.
Individual evidence
- ↑ a b c Conclusion regarding the peer review of the pesticide risk assessment of the active substance penconazole . In: EFSA Journal . tape 6 , no. 10 , 2008, ISSN 1831-4732 , p. 175r , doi : 10.2903 / j.efsa.2008.175r .
- ↑ Penconazole data sheet from Sigma-Aldrich , accessed on May 20, 2017 ( PDF ).
- ↑ Entry on Penconazole in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on April 2, 2020.
- ↑ a b c d Entry on penconazole. In: Römpp Online . Georg Thieme Verlag, accessed on November 15, 2014.
- ↑ a b c Entry on penconazole in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
- ↑ Entry on 1- [2- (2,4-dichlorophenyl) pentyl] -1H-1,2,4-triazole in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturer or distributor can expand the harmonized classification and labeling .
- ↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 715 ( limited preview in Google Book search).
- ↑ a b Directorate-General for Health and Food Safety of the European Commission: Entry on penconazole in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 25, 2016.