Pinoxades

Structural formula
General
Surname	Pinoxades
other names	8- (2,6-diethyl- p -tolyl) -1,2,4,5-tetrahydro-7-oxo-7 H -pyrazolo [1,2- d ] [1,4,5] oxadiazepine-9- yl 2,2-dimethyl propionate
Molecular formula	C 23 H 32 N 2 O 4
Brief description	odorless white solid
External identifiers / databases
EC number	635-361-9
ECHA InfoCard	100.163.258
PubChem	210326
Wikidata	Q15632855
properties
Molar mass	400.51 g mol −1
Physical state	firmly
density	1.16 g cm −3 (21 ° C)
Melting point	120.5-121.6 ° C
boiling point	335 ° C (decomposition)
solubility	practically insoluble in water (200 mg l −1 at 25 ° C); soluble in acetone, dichloromethane, ethyl acetate, methanol, 1-octanol and toluene;
safety instructions
H and P phrases	H: 302-317-319-332-335-361d-410
	P: 261-305 + 351 + 338
Toxicological data	> 5000 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 .

Pinoxaden is a synthetically produced chemical compound from the phenylpyrazoline group that is used as a herbicide .

Extraction and presentation

Pinoxaden can be synthesized by a thermal condensation of a cyclic hydrazine and an arylmalonamide (which in turn is obtained from 2,6-diethyltoluidine ). The resulting intermediate is converted into its enol ester pinoxaden under standard conditions.

properties

Pinoxaden is an odorless white solid, as a technical product a yellow-orange liquid with a smell of thymol . Its half-life to hydrolysis is between 0.2 days at a pH of 9 and 17 days at a pH of 5.

use

Pinoxaden is used as a herbicide. It was developed by Syngenta and is used against grasses. The effect is based on influencing the lipid metabolism of the cells. It inhibits acetyl-CoA carboxylase .

The approval process for pinoxades in the European Union has not yet been completed. After Syngenta submitted the documents for approval in March 2004, their completeness was determined in June 2005 by the EU Commission. If this is the case, the EU member states can issue provisional approvals for plant protection products containing this active ingredient. The authorizations to extend provisional approvals were extended for two years each in 2010 and 2012.

In Germany, Austria and Switzerland, plant protection products (e.g. Axial) containing this active ingredient are approved.

Individual evidence

↑ ^a ^b ^c ^d EPA: Pesticide Fact Sheet (PDF; 2.5 MB), July 2005.
↑ ^a ^b ^c Data sheet Pinoxaden at Sigma-Aldrich , accessed on December 30, 2019 ( PDF ).
↑ Entry on Pinoxaden in the GESTIS substance database of the IFA , accessed on December 30, 2019(JavaScript required) .
↑ ^a ^b ^c ^d ^e ^f BVL: Pinoxaden
↑ Entry on pinoxaden (ISO); 8- (2,6-diethyl-4-methylphenyl) -7-oxo-1,2,4,5-tetrahydro-7H-pyrazolo [1,2-d] [1,4,5] oxadiazepin-9-yl 2,2-dimethylpropanoate in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on December 30, 2019. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ ^a ^b Wolfgang Krämer, Ulrich Schirmer, Peter Jeschke, Matthias Witschel: Modern Crop Protection Compounds . Wiley-VCH, 2011, ISBN 978-3-527-32965-6 , pp. 470 ( limited preview in Google Book search).
↑ Hideo Ohkawa, Hisashi Miyagawa, Philip W. Lee: Pesticide Chemistry: Crop Protection, Public Health, Environmental Safety . John Wiley & Sons, 2007, ISBN 3-527-61125-8 , pp. 105 ( limited preview in Google Book search).
↑ Decision of the Commission of June 22, 2005 (PDF) on the fundamental recognition of the completeness of the documents submitted for detailed examination with regard to the possible inclusion of Pinoxaden in Annex I of Council Directive 91/414 / EEC (2010/353 / EU).
↑ Decision of the Commission of June 24, 2010 (PDF) authorizing the member states to extend provisional authorizations for the new active ingredients amisulbromine, chlorantraniliprole, meptyldinocap and pinoxaden (2010/353 / EU).
↑ Implementation decision of the Commission of April 10, 2012 (PDF) authorizing the member states to extend provisional authorizations for the new active substances amisulbrom, chlorantraniliprole, meptyldinocap, pinoxaden, silver thiosulphate and tembotrione (2012/191 / EU).
↑ General Directorate Health and Food Safety of the European Commission: Entry on Pinoxaden in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 23, 2016.

[EPA-1] EPA: Pesticide Fact Sheet (PDF; 2.5 MB), July 2005.

[Sigma-2] Data sheet Pinoxaden at Sigma-Aldrich , accessed on December 30, 2019 ( PDF ).

[GESTIS-3] Entry on Pinoxaden in the GESTIS substance database of the IFA , accessed on December 30, 2019(JavaScript required) .

[BVL-4] ↑ ^a ^b ^c ^d ^e ^f BVL: Pinoxaden

[CLP_100.163.258-5] Entry on pinoxaden (ISO); 8- (2,6-diethyl-4-methylphenyl) -7-oxo-1,2,4,5-tetrahydro-7H-pyrazolo [1,2-d] [1,4,5] oxadiazepin-9-yl 2,2-dimethylpropanoate in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on December 30, 2019. Manufacturers or distributors can expand the harmonized classification and labeling .

[ModernCPC-6] Wolfgang Krämer, Ulrich Schirmer, Peter Jeschke, Matthias Witschel: Modern Crop Protection Compounds . Wiley-VCH, 2011, ISBN 978-3-527-32965-6 , pp. 470 ( limited preview in Google Book search).

[Hideo_Ohkawa,_Hisashi_Miyagawa,_Dr._Philip_W._Lee-7] Hideo Ohkawa, Hisashi Miyagawa, Philip W. Lee: Pesticide Chemistry: Crop Protection, Public Health, Environmental Safety . John Wiley & Sons, 2007, ISBN 3-527-61125-8 , pp. 105 ( limited preview in Google Book search).

[8] Decision of the Commission of June 22, 2005 (PDF) on the fundamental recognition of the completeness of the documents submitted for detailed examination with regard to the possible inclusion of Pinoxaden in Annex I of Council Directive 91/414 / EEC (2010/353 / EU).

[9] Decision of the Commission of June 24, 2010 (PDF) authorizing the member states to extend provisional authorizations for the new active ingredients amisulbromine, chlorantraniliprole, meptyldinocap and pinoxaden (2010/353 / EU).

[10] Implementation decision of the Commission of April 10, 2012 (PDF) authorizing the member states to extend provisional authorizations for the new active substances amisulbrom, chlorantraniliprole, meptyldinocap, pinoxaden, silver thiosulphate and tembotrione (2012/191 / EU).

[PSM-11] General Directorate Health and Food Safety of the European Commission: Entry on Pinoxaden in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 23, 2016.