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Structural formula
Structural formula of pinoxades
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
CAS number 243973-20-8
EC number 635-361-9
ECHA InfoCard 100.163.258
PubChem 210326
Wikidata Q15632855
Molar mass 400.51 g mol −1
Physical state



1.16 g cm −3 (21 ° C)

Melting point

120.5-121.6 ° C

boiling point

335 ° C (decomposition)

  • practically insoluble in water (200 mg l −1 at 25 ° C)
  • soluble in acetone, dichloromethane, ethyl acetate, methanol, 1-octanol and toluene
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
07 - Warning 08 - Dangerous to health 09 - Dangerous for the environment


H and P phrases H: 302-317-319-332-335-361d-410
P: 261-305 + 351 + 338
Toxicological data
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.


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.


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

  1. a b c d EPA: Pesticide Fact Sheet (PDF; 2.5 MB), July 2005.
  2. a b c Data sheet Pinoxaden at Sigma-Aldrich , accessed on December 30, 2019 ( PDF ).
  3. Entry on Pinoxaden in the GESTIS substance database of the IFA , accessed on December 30, 2019(JavaScript required) .
  4. a b c d e f BVL: Pinoxaden
  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 .
  6. 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).
  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).
  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.