Flutolanil

Structural formula
General
Surname	Flutolanil
other names	α-α-α-trifluoro-3'-isopropoxy- o -toluanilide; N - [3- (1-methylethoxy) phenyl] -2- (trifluoromethyl) benzamide;
Molecular formula	C 17 H 16 F 3 NO 2
Brief description	yellowish solid with a slight chemical odor
External identifiers / databases
EC number	613-921-3
ECHA InfoCard	100.124.630
PubChem	47898
ChemSpider	43579
Wikidata	Q2338052
properties
Molar mass	323.34 g mol −1
Physical state	firmly
density	1.321 g cm −3
Melting point	103.9-105.2 ° C
boiling point	300 ° C (decomposition)
Vapor pressure	4.1 10 −7 Pa (20 ° C)
solubility	practically insoluble in water (8 mg l −1 at 20 ° C); soluble in acetone, acetonitrile, dichloromethane, ethyl acetate, methanol and toluene;
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
Toxicological data	10,000 mg kg −1 ( LD 50 , rat , oral ) ; 5,000 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 .

Flutolanil is a chemical compound from the group of amides , more precisely the benzamides .

Extraction and presentation

Flutolanil can be obtained by reacting 3-chloroaniline with sodium isopropoxylate and 2-trifluoromethylbenzoyl chloride:

properties

Flutolanil is a yellowish solid with a slight chemical odor that is practically insoluble in water. The compound is stable under neutral, basic and acidic conditions.

use

Flutolanil is used as a fungicide . It is used to control basidiomycetes in rice, grain, sugar beet, and other crops. Flutolanil is a systemic fungicide that works by inhibiting succinate dehydrogenase . It was brought onto the market in 1986 by the Japanese company Nihon Nōyaku .

Admission

The active ingredient was approved for use as a fungicide in the European Union with effect from March 1, 2009.

In many EU countries, including Germany and Austria, as well as Switzerland, plant protection products with this active ingredient are approved, but none in Austria.

Individual evidence

↑ ^a ^b ^c ^d FAO: Flutolanil (PDF; 366 kB)
↑ ^a ^b ^c ^d data sheet Flutolanil, analytical standard at Sigma-Aldrich , accessed on March 28, 2013 ( PDF ).
↑ ^a ^b ^c ^d ^e BVL: Flutolanil
↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-08-095716-1 , pp. 28 ( 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. 1145 ( limited preview in Google Book search).
↑ Ulrich Schirmer, Peter Jeschke, Matthias Witschel: Modern Crop Protection Compounds: Herbicides . John Wiley & Sons, 2012, ISBN 978-3-527-32965-6 , pp. 628 ( limited preview in Google Book search).
↑ Commission Directive 2008/108 / EC of November 26, 2008 amending Council Directive 91/414 / EEC to include the active substances flutolanil, benfluralin, fluazinam, fuberidazole and mepiquat (PDF)
↑ General Directorate Health and Food Safety of the European Commission: Entry on Flutolanil in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 23, 2016.

[FAO-1] FAO: Flutolanil (PDF; 366 kB)

[Sigma-2] ta sheet Flutolanil, analytical standard at Sigma-Aldrich , accessed on March 28, 2013 ( PDF ).

[bvl-3] BVL: Flutolanil

[Thomas_A._Unger-4] Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-08-095716-1 , pp. 28 ( limited preview in Google Book search).

[Terence_Robert_Roberts,_David_Herd_Hutson-5] 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. 1145 ( limited preview in Google Book search).

[Ulrich_Schirmer,_Peter_Jeschke,_Matthias_Witschel-6] Ulrich Schirmer, Peter Jeschke, Matthias Witschel: Modern Crop Protection Compounds: Herbicides . John Wiley & Sons, 2012, ISBN 978-3-527-32965-6 , pp. 628 ( limited preview in Google Book search).

[7] Commission Directive 2008/108 / EC of November 26, 2008 amending Council Directive 91/414 / EEC to include the active substances flutolanil, benfluralin, fluazinam, fuberidazole and mepiquat (PDF)

[PSM-8] General Directorate Health and Food Safety of the European Commission: Entry on Flutolanil in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 23, 2016.