Myclobutanil
Structural formula | |||||||||||||||||||
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Structural formula without specifying the stereochemistry (stereocenter is marked with a * ) | |||||||||||||||||||
General | |||||||||||||||||||
Surname | Myclobutanil | ||||||||||||||||||
other names |
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Molecular formula | C 15 H 17 ClN 4 | ||||||||||||||||||
Brief description |
pale yellow crystals |
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properties | |||||||||||||||||||
Molar mass | 288.77 g · mol -1 | ||||||||||||||||||
Physical state |
firmly |
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density |
1.22 g cm −3 |
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Melting point |
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boiling point |
202-208 ° C (133 Pa) |
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Vapor pressure |
0.213 mPa (25 ° C) |
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solubility |
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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 . |
Myclobutanil is a racemic mixture of two enantiomeric chemical compounds from the group of the triazoles , nitriles and chlorophenyls and a systemic azole fungicide developed by Rohm and Haas in the late 1980s .
Stereoisomerism
Myclobutanil is a 1: 1 mixture ( racemate ) of the ( R ) - and ( S ) -configured enantiomer.
Enantiomers of myclobutanil | ||
Surname | ( S ) -Myclobutanil | ( R ) -Myclobutanil |
other names | (-) - myclobutanil | (+) - myclobutanil |
Structural formula | ||
CAS number | 244094-39-1 | 244094-40-4 |
88671-89-0 (mixture of isomers) | ||
EC number | 410-400-0, 618-198-8 (mixture of isomers) | |
ECHA info card | 100.101.000 , 100.115.883 (mixture of isomers) | |
PubChem | 38989055 | 11077077 |
6336 (mixture of isomers) | ||
Wikidata | Q27157152 | Q27157150 |
Q413587 (mixture of isomers) |
synthesis
In the production of myclobutanil, 4-chlorophenylacetonitrile and 1-chlorobutane first react with one another. A bromomethane group is then added by reaction with dibromomethane . The bromine is substituted with 1,2,4-triazole in the last step .
use
Myclobutanil is used as a broad-spectrum fungicide in agriculture and in home gardens (especially in ornamental plants, fruit trees and in viticulture against scab , rust and mildew ).
The action is based on inhibition of ergosterol - biosynthesis .
Admission
Myclobutanil is approved as an active ingredient in plant protection products in many EU countries, including Germany and Austria, and Switzerland.
safety instructions
Myclobutanil is only slightly toxic to humans. In animal experiments, damage to embryos was demonstrated at high doses. It is highly toxic to fish, algae and zooplankton .
Individual evidence
- ↑ a b c Entry on myclobutanil. In: Römpp Online . Georg Thieme Verlag, accessed on May 14, 2014.
- ↑ a b c d e Decision Document of the Plant Industry Directorate of Canada ( Memento of October 5, 2006 in the Internet Archive ).
- ↑ entry to myclobutanil at ChemBlink , accessed on February 25 2011th
- ↑ Product Sheet .
- ↑ a b Entry on myclobutanil in the GESTIS substance database of the IFA , accessed on January 15, 2020(JavaScript required) .
- ↑ Entry on α-n-butyl-α- (4-chlorophenyl) -1H-1,2,4-triazole-1-propanenitrile in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturer or distributors can expand the harmonized classification and labeling .
- ↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 714 ( limited preview in Google Book search).
- ^ Joint Meeting on Pesticide Residues (JMPR), Monograph for Myclobutanil , accessed December 9, 2014.
- ↑ Directorate-General for Health and Food Safety of the European Commission: Entry on myclobutanil in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 13, 2016.