Chemistry:Bixafen
Bixafen is a chemical compound belonging to the groups of pyrazoles, carboxamides, and biphenyls.
Synthesis and Preparation
Bixafen can be prepared by reductive Suzuki–Miyaura coupling of the potassium salt of 2-nitro-5-fluorobenzoic acid with 3,4-dichlorobromobenzene to form the corresponding biaryl compound, followed by reaction with the pyrazole carboxylic acid chloride (1-methyl-3-(difluoromethyl)-4-chlorocarbonyl-1H-pyrazole) in the presence of a base such as triethylamine.[1][2]
Properties
Bixafen is a colorless solid that is practically insoluble in water.[3] It is stable to hydrolysis.[4]
Uses
Bixafen is used as a fungicide on cereal crops.[4] It was introduced to the market by Bayer in 2011.[5] Its mode of action is based on the inhibition of succinate dehydrogenase.[6] Combination formulations with prothioconazole and other compounds are also used.[7]
Approval
The active ingredient was approved by the European Commission with effect from October 1, 2013.[8]
In a number of EU countries, including Germany and Austria, as well as in Switzerland, pesticides (e.g., Aviator Xpro) containing this active ingredient are approved.[9]
References
- ↑ Clemens Lamberth, Jürgen Dinges (2012), Bioactive Heterocyclic Compound Classes: Agrochemicals, John Wiley & Sons, pp. 103, ISBN 352766443-2, https://books.google.com/books?id=dRRR0mB3R_oC&pg=PA103
- ↑ L. J. Gooßen, C. Linder, Saltigo GmbH, WO002008122555A1, 2008.
- ↑ EFSA: Conclusion on the peer review of the pesticide risk assessment of the active substance bixafen, EFSA Journal 2012;10(11):2917
- ↑ 4.0 4.1 BVL: Bixafen
- ↑ Wolfgang Krämer, Ulrich Schirmer, Peter Jeschke, Matthias Witschel (2011), Modern Crop Protection Compounds, Wiley-VCH, pp. 630, ISBN 978-3527329656, https://books.google.com/books?id=rZsaM-K2vdMC&pg=PA630
- ↑ C.A. Berdugo, U. Steiner, H.-W. Dehne, E.-C. Oerke: Effect of bixafen on senescence and yield formation of wheat. In: Pesticide Biochemistry and Physiology. 104, 2012, S. 171–177, doi:10.1016/j.pestbp.2012.07.010.
- ↑ Bayer CropScience: Xpro Technology
- ↑ Template:EUR-Lex link
- ↑ "EU Pesticides Database". https://ec.europa.eu/food/plant/pesticides/eu-pesticides-database/start/screen/active-substances/details/675.
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