Metrafenone

Structural formula
General
Surname	Metrafenone
other names	3'-Bromo-2,3,4,6'-tetramethoxy-2 ', 6-dimethylbenzophenone
Molecular formula	C 19 H 21 BrO 5
Brief description	white to yellowish solid with a slightly musty odor
External identifiers / databases
EC number	606-928-8
ECHA InfoCard	100.133.245
PubChem	6451057
ChemSpider	4953549
Wikidata	Q1925667
properties
Molar mass	409.27 g mol −1
Physical state	firmly
density	1.45 g m −3
Melting point	99.2-100.8 ° C
boiling point	310 ° C (decomposition)
solubility	practically insoluble in water (0.47 mg l −1 at 20 ° C); soluble in dichloromethane , acetone and toluene ;
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 410
	P: 273-391-501
Toxicological data	> 5000 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Metrafenone is an active ingredient for crop protection and a chemical compound from the group of benzophenone derivatives .

Extraction and presentation

Metrafenone can be synthesized by an iron (III) chloride catalyzed Friedel-Crafts acylation of 3,4,5-trimethoxytoluene . The associated benzoyl chloride can easily be obtained by bromination of 2-methoxy-6-methyl-benzoic acid and subsequent conversion into the acid chloride .

properties

Metrafenone is a flammable off-white solid that is practically insoluble in water.

use

Metrafenone is used as an active ingredient in plant protection products. In 2007, metrafenone was approved as a fungicidal active ingredient in plant protection products in the European Union. In 2008 it was introduced by BASF as a fungicide in Central and Southeastern Europe.

In Switzerland, Austria and Germany, metrafenone is approved in pesticides for use against fungal diseases in grain and against powdery mildew in viticulture.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on metrafenone in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .
↑ ^a ^b EPA: metrafenone
↑ BVL: Metrafenone
↑ Wolfgang Krämer, Ulrich Schirmer, Peter Jeschke, Matthias Witschel: Modern Crop Protection Compounds . Wiley-VCH, 2011, ISBN 978-3-527-32965-6 , pp. 892 (English, limited preview in Google Book search).
↑ Commission Directive 2007/6 / EC of February 14, 2007 amending Council Directive 91/414 / EEC to include the active substances metrafenone, Bacillus subtilis, spinosad and thiamethoxam
↑ Seedquest: BASF Crop Protection is growing faster than the market in Eastern Europe , May 27, 2008.
↑ General Directorate Health and Food Safety of the European Commission: Entry on Metrafenone in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 12, 2016.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on metrafenone in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .

[EPA-2] EPA: metrafenone

[3] BVL: Metrafenone

[ModernCPC-4] Wolfgang Krämer, Ulrich Schirmer, Peter Jeschke, Matthias Witschel: Modern Crop Protection Compounds . Wiley-VCH, 2011, ISBN 978-3-527-32965-6 , pp. 892 (English, limited preview in Google Book search).

[5] Commission Directive 2007/6 / EC of February 14, 2007 amending Council Directive 91/414 / EEC to include the active substances metrafenone, Bacillus subtilis, spinosad and thiamethoxam

[Seedquest-6] Seedquest: BASF Crop Protection is growing faster than the market in Eastern Europe , May 27, 2008.

[PSM-7] General Directorate Health and Food Safety of the European Commission: Entry on Metrafenone in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 12, 2016.