Bitertanol
_Bitertanol_Structural_Formula_V1.svg) | |
| Identifiers | |
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| ECHA InfoCard | 100.054.084 |
PubChem CID |
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CompTox Dashboard (EPA) |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Bitertanol is a mixture of four isomers, which are chemical compounds belonging to the triazole and biphenyl derivative classes.
Synthesis and Preparation
[edit]Bitertanol can be prepared via a multi-step reaction starting from 3,3-dimethyl-2-butanone: chlorination with elemental chlorine is followed by nucleophilic substitution of the chlorine atom with 4-phenylphenol, bromination with elemental bromine, subsequent nucleophilic substitution with 1,2,4-triazole, and final reduction of the ketone with hydrogen.[1]
Properties
[edit]Bitertanol is a colorless, water-insoluble solid.[2] The commercial product is a 20:80 mixture of the (1RS,2RS)- and (1RS,2SR)-isomers.
- Stereoisomers of bitertanol, showing the Cahn-Ingold-Prelog convention-configuration and content in the technical product
(1R,2R)-bitertanol (approx. 10%)
(1S,2S)-Bitertanol (approx. 10%)
(1R,2S)-Bitertanol (approx. 40%)
(1S,2R)-Bitertanol (approx. 40%)
_Bitertanol_Structural_Formula_V1.svg)
_Bitertanol_Structural_Formula_V1.svg)
_Bitertanol_Structural_Formula_V1.svg)
_Bitertanol_Structural_Formula_V1.svg)
It is highly stable toward photolysis and hydrolysis.[3][4] Its half-life in aqueous suspension is 39.2 days.[5]
Uses
[edit]Bitertanol is used as a fungicide for the preventive or curative treatment of diseases in fruit and vegetable crops, including Venturia species and Monilia laxa in stone fruit, as well as a seed treatment against Fusarium, Septoria, wheat scab, and other pathogens.[6] It was introduced to the market in 1979 by Bayer AG.[7]
Approval
[edit]The European Union approved its use as an active substance in plant protection products, effective January 1, 2012, specifically as a fungicide for seed treatment.[8] This approval expired in August 2013.
In European countries such as Germany and Austria, as well as Switzerland, no plant protection products containing this active substance are approved.[9]
References
[edit]- ↑ Thomas A. Unger (1996), Pesticide Synthesis Handbook, William Andrew, p. 685, ISBN 0-08-095716-1
- ↑ Sigma-Aldrich Co., product no. {{{id}}}.
- ↑ EFSA: Conclusion on the peer review of the pesticide risk assessment of the active substance bitertanol, 2010. doi:10.2903/j.efsa.2010.1850
- ↑ Terence Robert Roberts, David Herd Hutson (1999), Metabolic Pathways of Agrochemicals: Part 2, Insecticides and fungicides, Royal Society of Chemistry, p. 1018, ISBN 0-85404-499-X
- ↑ F. Müller, P. Ackermann, P. Margot: Fungicides, Agricultural, 2. Individual Fungicides. In: Ullmanns Enzyklopädie der Technischen Chemie. Wiley-VCH, Weinheim 2012, doi:10.1002/14356007.o12_o06.
- ↑ FAO: Bitertanol (PDF; 548 kB).
- ↑ Ulrich Schirmer, Peter Jeschke, Matthias Witschel (2012), Modern Crop Protection Compounds: Herbicides, John Wiley & Sons, p. 771, ISBN 978-3-527-32965-6
{{citation}}: CS1 maint: multiple names: authors list (link) - ↑ Template:EUR-Lex-Rechtsakt.
- ↑ Template:PSM-Verz