Bitertanol
Structural formula | ||||||||||||||||
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General structural formula without information on stereochemistry - mixture of four isomers | ||||||||||||||||
General | ||||||||||||||||
Surname | Bitertanol | |||||||||||||||
other names |
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Molecular formula | C 20 H 23 N 3 O 2 | |||||||||||||||
Brief description |
colorless solid |
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properties | ||||||||||||||||
Molar mass | 337.42 g mol −1 | |||||||||||||||
Physical state |
firmly |
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density |
1.16 g cm −3 |
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Melting point |
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boiling point |
300 ° C (decomposition) |
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Vapor pressure |
1.36 nPa (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 . |
Bitertanol is a mixture of four isomeric chemical compounds from the groups of the triazoles and the biphenyl - derivatives .
Extraction and presentation
Bitertanol can be produced by a multi-stage reaction of 3,3-dimethylbutan-1-one by chlorination with elemental chlorine , by subsequent nucleophilic substitution of the chlorine atom with 4-phenylphenol , bromination with elemental bromine , renewed nucleophilic substitution with 1,2,4-triazole and reducing the ketone with hydrogen .
properties
Bitertanol is a colorless solid that is insoluble in water. The technical product is a 20:80 mixture of the (1 RS , 2 RS ) and (1 RS , 2 SR ) isomers .
It is very stable to photolysis and hydrolysis . The half-life in aqueous suspension is 39.2 days.
use
Bitertanol is used as a preventive or curative fungicide to combat certain diseases in fruit and vegetables, including scab and Monilia laxa in stone fruit, and to treat seeds against Fusarium spp. , Septoria , Weizensteinbrand etc. It was brought onto the market by Bayer in 1979 .
Admission
The European Union allowed its use as an active ingredient in plant protection products with effect from January 1, 2012 for applications as a fungicide for seed treatment .
In Germany, Austria and Switzerland, no pesticides with this active ingredient are permitted.
Individual evidence
- ↑ a b c d e f g Bitertanol data sheet , PESTANAL at Sigma-Aldrich , accessed on May 19, 2017 ( PDF ).
- ↑ a b c F. Müller, P. Ackermann, P. Margot: Fungicides, Agricultural, 2. Individual Fungicides. In: Ullmann's Encyclopedia of Technical Chemistry . Wiley-VCH, Weinheim 2012, doi : 10.1002 / 14356007.o12_o06 .
- ↑ a b c d e f EFSA: Conclusion on the peer review of the pesticide risk assessment of the active substance bitertanol , 2010. doi : 10.2903 / j.efsa.2010.1850
- ↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-08-095716-1 , pp. 685 ( limited preview in Google Book search).
- ^ Terence Robert Roberts, David Herd Hutson: Metabolic Pathways of Agrochemicals: Part 2, Insecticides and fungicides . Royal Society of Chemistry, 1999, ISBN 0-85404-499-X , pp. 1018 ( limited preview in Google Book search).
- ↑ FAO: Bitertanol (PDF; 548 kB).
- ↑ Ulrich Schirmer, Peter Jeschke, Matthias Witschel: Modern Crop Protection Compounds: Herbicides . John Wiley & Sons, 2012, ISBN 978-3-527-32965-6 , pp. 771 ( limited preview in Google Book search).
- ↑ Implementing Regulation (EU) No. 1278/2011 of the Commission of December 8, 2011 for the approval of the active ingredient Bitertanol according to Regulation (EC) No. 1107/2009 ... (PDF) .
- ↑ General Directorate Health and Food Safety of the European Commission: Entry on Bitertanol in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 22, 2016.