Isoxaflutole

Structural formula
General
Surname	Isoxaflutole
other names	5-Cyclopropyl-1,2-oxazol-4-yl-α, α, α-trifluoro-2-mesyl- p -tolyl ketone; (5-Cyclopropyl-4-isoxazolyl) - [2- (methylsulfonyl) -4- (trifluoromethyl) phenyl] methanone;
Molecular formula	C 15 H 12 F 3 NO 4 S
Brief description	White dust
External identifiers / databases
EC number	604-222-4
ECHA InfoCard	100.114.433
PubChem	84098
ChemSpider	75869
DrugBank	DB12938
Wikidata	Q15632908
properties
Molar mass	359.32 g mol −1
Physical state	firmly
density	1.59 g cm −3
Melting point	140 ° C
solubility	almost insoluble in water (6.2 mg l −1 at 20 ° C)
safety instructions
H and P phrases	H: 361d-410
	P: 273-281-501
Toxicological data	> 5000 mg kg −1 ( LD 50 , rat , oral ) ; > 2000 mg kg −1 ( LD 50 , rabbit , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Isoxaflutole is a chemical compound from the group of oxazoles , more precisely the cyclopropylisoxazoles .

Extraction and presentation

Isoxaflutole can be obtained by reacting 1- (4-trifluoromethyl-2-methylsulfonylphenyl) -3-cyclopropyl-2-ethoxymethylene-propane-1,3-dione with hydroxylamine .

properties

Isoxaflutole is a white solid that is insoluble in water. It is stable as a solid and in solution at pH values of 6 and below.

use

Isoxaflutole is used as an active ingredient in crop protection products. It has been used as a herbicide against grasses and broad-leaved weeds such as Abutilon theophrasti , Amaranthus retroflexus , Setaria faberi , Setaria viridis and Panicum species in corn and sugar beet since its market launch in 1995 . The effect is based on the inhibition of the enzyme 4-hydroxyphenylpyruvate dioxygenase (HPPD).

Bayer CropScience markets isoxaflutole together with the safener cyprosulfamide as Balance Flexx .

Soybeans that are tolerant of isoxaflutole have been on the market in the USA since 2012 . Approval of isoxaflutole for soybeans is therefore expected.

Admission

In Europe, the French company Rhône-Poulenc Secteur Agro applied for inclusion in Annex I of Directive 91/414 / EEC on March 6, 1996 . In the European Union, isoxaflutole has been approved for use as a herbicide since October 2003. It was approved in the US in 1998.

In Germany, Austria and Switzerland, pesticides (e.g. Adengo and Merlin) with this active ingredient are approved.

Individual evidence

↑ ^a ^b ^c ^d ^e data sheet isoxaflutole from Sigma-Aldrich , accessed on May 21, 2017 ( PDF ).
↑ ^a ^b ^c ^d ^e Entry on isoxaflutole in the GESTIS substance database of the IFA , accessed on February 5, 2017(JavaScript required) .
↑ Entry on 5-cyclopropyl-1,2-oxazol-4-yl-α, α, α-trifluoro-2-mesyl-p-tolyl ketone in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on April 1, 2017 Manufacturers or distributors can expand the harmonized classification and labeling .
↑ Entry on isoxaflutole in the Hazardous Substances Data Bank , accessed January 11, 2013.
^ ^A ^b Terence Robert Roberts, DH Hutson: Metabolic pathways of agrochemicals . tape 2 . Royal Soc of Chemistry, 1999, ISBN 978-0-85404-499-3 , pp. 379 ( limited preview in Google Book search).
↑ Bayer Balance Flexx Herbicide. Bayer AG , accessed on August 22, 2017 .
↑ ISAAA: GM Events with Isoxaflutole herbicide tolerance
↑ Minnesota New Active Ingredient Review , May 2015
↑ 96/524 / EC: Commission decision of July 29, 1996 on the fundamental recognition of the completeness of the documents required for detailed examination with regard to a possible inclusion of isoxaflutole in Annex I of Council Directive 91/414 / EEC on the Placing of plant protection products on the market (text with EEA relevance) , Official Journal No. L 220 of 30/08/1996 pp. 0027–0028.
↑ Directive 2003/68 / EC of the Commission of July 11, 2003 amending Council Directive 91/414 / EEC to include the active substances trifloxystrobin, carfentrazone-ethyl, mesotrione, fenamidone and isoxaflutole (PDF)
↑ EPA: Isoxaflutole Summary Document Registration Review: Initial Docket June 2011. Retrieved August 22, 2017.
^ Directorate-General for Health and Food Safety of the European Commission: Entry on isoxaflutole in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 13, 2016.

[Sigma-1] ↑ ^a ^b ^c ^d ^e data sheet isoxaflutole from Sigma-Aldrich , accessed on May 21, 2017 ( PDF ).

[GESTIS-2] Entry on isoxaflutole in the GESTIS substance database of the IFA , accessed on February 5, 2017(JavaScript required) .

[CLP_100.114.433-3] Entry on 5-cyclopropyl-1,2-oxazol-4-yl-α, α, α-trifluoro-2-mesyl-p-tolyl ketone in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on April 1, 2017 Manufacturers or distributors can expand the harmonized classification and labeling .

[HSDB-4] Entry on isoxaflutole in the Hazardous Substances Data Bank , accessed January 11, 2013.

[Roberts2-5] A ^b Terence Robert Roberts, DH Hutson: Metabolic pathways of agrochemicals . tape 2 . Royal Soc of Chemistry, 1999, ISBN 978-0-85404-499-3 , pp. 379 ( limited preview in Google Book search).

[6] Bayer Balance Flexx Herbicide. Bayer AG , accessed on August 22, 2017 .

[7] ISAAA: GM Events with Isoxaflutole herbicide tolerance

[8] Minnesota New Active Ingredient Review , May 2015

[9] 96/524 / EC: Commission decision of July 29, 1996 on the fundamental recognition of the completeness of the documents required for detailed examination with regard to a possible inclusion of isoxaflutole in Annex I of Council Directive 91/414 / EEC on the Placing of plant protection products on the market (text with EEA relevance) , Official Journal No. L 220 of 30/08/1996 pp. 0027–0028.

[10] Directive 2003/68 / EC of the Commission of July 11, 2003 amending Council Directive 91/414 / EEC to include the active substances trifloxystrobin, carfentrazone-ethyl, mesotrione, fenamidone and isoxaflutole (PDF)

[EPA-11] EPA: Isoxaflutole Summary Document Registration Review: Initial Docket June 2011. Retrieved August 22, 2017.

[PSM-12] Directorate-General for Health and Food Safety of the European Commission: Entry on isoxaflutole in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 13, 2016.