Profoxydim

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Structural formula
Structural formula of Profoxydim
Complex mixture of isomers - simplified structural formula
without information on stereochemistry
General
Surname Profoxydim
other names
  • (5 RS ) -2 - {( EZ ) -1 - [(2 RS ) -2- (4-chlorophenoxy) propoxyimino] butyl} -3-hydroxy-5 - [(3 RS ) -thian-3-yl] cyclohex-2-en-1-one
  • 2 - (( EZ ) -1 - ((2 RS ) -2- (4-chlorophenoxy) propoxyimino) butyl) -3-hydroxy-5- (thian-3-yl) cyclohex-2-en-1-one
  • 2- { N - [2- (4-chlorophenoxy) propoxybutane] imidoyl} -3-hydroxy-5-tetrahydro-2 H -thiopyran-3-ylcyclohex-2-en-1-one
  • Clefoxydim
Molecular formula C 24 H 32 ClNO 4 S
Brief description

colorless and odorless liquid

External identifiers / databases
CAS number
  • 139001-49-3
  • 281664-76-4 (lithium salt)
EC number 604-105-8
ECHA InfoCard 100.111.215
PubChem 197395
ChemSpider 170923
Wikidata Q2014243
properties
Molar mass 466.03 g mol −1
Physical state

liquid

density

1.198 g cm −3

Melting point

150–200 ° C (decomposition)

Vapor pressure

1.7 10 −6 hPa (20 ° C)

solubility
  • practically insoluble in water (27.8 mg l −1 at 20 ° C)
  • soluble in methanol, acetone, 2-propanol, ethyl acetate, acetonitrile, dichloromethane, toluene and 1-octanol
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
08 - Dangerous to health 07 - Warning

Caution

H and P phrases H: 351-361d-317
P: 280
Toxicological data
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Profoxydim is a mixture of several isomeric chemical compounds from the group of cyclohexene oximes . Profoxydim was introduced by BASF in 1998 .

properties

Profoxydim is a colorless and odorless liquid. It is stable to hydrolysis and photolysis , but is changing depending on the pH value by oxidation in sulfoxides to ( DT 50 value between 30 and 300 days).

Stereochemistry

The profoxydim molecule has several stereocenters : the carbon atoms C-2 (in the isopropyl group ) and C-5 (linking atom of the thiopyran radical ) are asymmetrically substituted and therefore chiral ; at the oxime moiety can also ( EZ ) isomerism occur. In the cyclohexanone ring there is an enol grouping that enables keto-enol tautomerism .

The isomers are usually used as a mixture.

use

Profoxydim is used as a systemic herbicide in rice cultivation.

The active ingredient inhibits acetyl-CoA carboxylase in fatty acid biosynthesis.

Admission

In some EU countries, plant protection products with this active ingredient are approved, but not in Germany, Austria or Switzerland.

Individual evidence

  1. ↑ a b c d e f g h i j k l EU: Review report for the active substance profoxydim, Finalized in the Standing Committee on the Food Chain and Animal Health at its meeting on, January 28, 2011
  2. ^ Entry on Profoxydim in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
  3. ↑ Entry to 2 - {(EZ) -1 - [(2RS) -2- (4-chlorophenoxy) propoxyimino] butyl} -3-hydroxy-5- (thian-3-yl) cyclohex-2-en-1- one Template: Linktext-Check / Escaped in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
  4. ↑ Data sheet Profoxydim lithium salt from Sigma-Aldrich , accessed on May 22, 2017 ( PDF ).
  5. ↑ a b c Entry on Profoxydim. In: Römpp Online . Georg Thieme Verlag, accessed on March 24, 2015.
  6. ↑ General Directorate Health and Food Safety of the European Commission: Entry on Profoxydim in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 25, 2016.