Bixafen

Structural formula
General
Surname	Bixafen
other names	N - (3 ′, 4′-dichloro-5-fluorobiphenyl-2-yl) -3- (difluoromethyl) -1-methylpyrazole-4-carboxamide ( IUPAC ); N - (3 ', 4'-dichloro-5-fluoro (1,1'-biphenyl) -2-yl) -3- (difluoromethyl) -1-methyl-1 H -pyrazole-4-carboxamide;
Molecular formula	C 18 H 12 Cl 2 F 3 N 3 O
Brief description	White dust
External identifiers / databases
EC number	642-423-9
ECHA InfoCard	100.170.250
PubChem	11434448
Wikidata	Q2040219
properties
Molar mass	414.21 g mol −1
Physical state	firmly
Melting point	146.6 ° C
boiling point	250–305 ° C (decomposition)
Vapor pressure	1.1 · 10 −7 Pa (25 ° C)
solubility	practically insoluble in water (0.49 g l −1 at 20 ° C); soluble in acetone and dichloromethane;
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 400
	P: 273
Toxicological data	> 2000 mg kg −1 ( LD 50 , rat , oral ) ; > 2000 mg kg −1 ( LD 50 , rat , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Bixafen is a chemical compound from the group of pyrazoles , carboxamides and biphenyls .

Extraction and presentation

Bixafen can be converted by a reductive Suzuki-Miyaura coupling of the potassium salt of 2-nitro-5-fluorobenzoic acid with 3,4-dichlorobromobenzene to the corresponding biaryl compound and further reaction with a pyrazole acid chloride (3- (difluoromethyl) -1-methyl-1 H - pyrazole-4-chlorocarbonyl) in the presence of a base such as triethylamine .

properties

Bixafen is a colorless solid that is practically insoluble in water. It is stable to hydrolysis .

use

Bixafen is used as a fungicide on cereals. It was launched by Bayer in 2011. The effect is based on the inhibition of succinate dehydrogenase . Combination preparations with prothioconazole and other compounds are also used.

Admission

The approval of the active ingredient by the EU Commission took effect on October 1, 2013.

In a number of EU countries, including Germany and Austria, as well as Switzerland, plant protection products (e.g. Aviator Xpro) containing this active ingredient are approved.

Individual evidence

↑ ^a ^b EFSA: Conclusion on the peer review of the pesticide risk assessment of the active substance bixafen , EFSA Journal 2012; 10 (11): 2917
↑ ^a ^b ^c ^d ^e data sheet Bixafen at Sigma-Aldrich , accessed on May 22, 2017 ( PDF ).
↑ ^a ^b ^c ^d ^e ^f ^g BVL: Bixafen
^ Clemens Lamberth, Jürgen Dinges: Bioactive Heterocyclic Compound Classes: Agrochemicals . John Wiley & Sons, 2012, ISBN 3-527-66443-2 , pp. 103 ( limited preview in Google Book search).
↑ LJ Goossen, C. Linder, Saltigo GmbH, WO002008122555A1, 2008.
↑ Wolfgang Krämer, Ulrich Schirmer, Peter Jeschke, Matthias Witschel: Modern Crop Protection Compounds . Wiley-VCH, 2011, ISBN 978-3-527-32965-6 , pp. 630 ( limited preview in Google Book search).
↑ CA 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, pp. 171–177, doi : 10.1016 / j.pestbp.2012.07.010 .
^ Bayer CropScience: Xpro Technology
↑ Implementing Regulation (EU) No. 350/2013 of the Commission of April 17, 2013 (PDF) for the approval of the active substance bixafen according to Regulation (EC) No. 1107/2009 of the European Parliament and of the Council on the placing of plant protection products on the market and amending it of the Annex of the Commission Implementing Regulation (EU) No. 540/2011.
^ Directorate-General for Health and Food Safety of the European Commission: Entry on Bixafen in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved February 20, 2016.

[EFSA-1] EFSA: Conclusion on the peer review of the pesticide risk assessment of the active substance bixafen , EFSA Journal 2012; 10 (11): 2917

[Sigma-2] ↑ ^a ^b ^c ^d ^e data sheet Bixafen at Sigma-Aldrich , accessed on May 22, 2017 ( PDF ).

[BVL-3] ↑ ^a ^b ^c ^d ^e ^f ^g BVL: Bixafen

[Clemens_Lamberth,_Jürgen_Dinges-4] Clemens Lamberth, Jürgen Dinges: Bioactive Heterocyclic Compound Classes: Agrochemicals . John Wiley & Sons, 2012, ISBN 3-527-66443-2 , pp. 103 ( limited preview in Google Book search).

[5] LJ Goossen, C. Linder, Saltigo GmbH, WO002008122555A1, 2008.

[ModernCPC-6] Wolfgang Krämer, Ulrich Schirmer, Peter Jeschke, Matthias Witschel: Modern Crop Protection Compounds . Wiley-VCH, 2011, ISBN 978-3-527-32965-6 , pp. 630 ( limited preview in Google Book search).

[DOI10.1016/j.pestbp.2012.07.010-7] CA 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, pp. 171–177, doi : 10.1016 / j.pestbp.2012.07.010 .

[Source-8] Bayer CropScience: Xpro Technology

[9] Implementing Regulation (EU) No. 350/2013 of the Commission of April 17, 2013 (PDF) for the approval of the active substance bixafen according to Regulation (EC) No. 1107/2009 of the European Parliament and of the Council on the placing of plant protection products on the market and amending it of the Annex of the Commission Implementing Regulation (EU) No. 540/2011.

[PSM-10] Directorate-General for Health and Food Safety of the European Commission: Entry on Bixafen in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved February 20, 2016.