Haloxyfop

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Haloxyfop is a group of structurally similar chemical compounds that differ in the carboxylic acid residue and in their stereochemical configuration . The ( R ) - isomer of the free acid and its methyl ester are used as herbicides under the names Haloxyfop-P or Haloxyfop-P-methyl and act by inhibiting acetyl-CoA carboxylase . Haloxyfop-P-methyl belongs to the aryloxyphenoxypropionate class of herbicides and is sold under the trade names Gallant , Zellk and Verdict .

Extraction and presentation

Haloxyfop-methyl can be obtained through a multi-stage reaction. The synthesis starts from propionic acid , which is chlorinated and reacts with methanol and hydroquinone . The intermediate product then reacts with 3-methyltrifluoro-5,6-dichloropyridine (from 3-picoline ) to form haloxyfop-methyl.

Synthesis of Haloxyfop-methyl.svg

Representative

Haloxyfop variants
Surname Haloxyfop
  • Haloxyfop-P
  • Haloxyfop-R
 Haloxyfop-etotyl Haloxyfop-methyl Haloxyfop-P-methyl Haloxyfop sodium
Structural formula Haloxyfop Haloxyfop-P Haloxyfop-etotyl Haloxyfop-methyl Haloxyfop-P-methyl Haloxyfop sodium
Configuration of
the stereocenter 		unspec. ( R ) unspec. unspec. ( R ) unspec.
CAS number 69806-34-4 95977-29-0 87237-48-7 69806-40-2 72619-32-0 69806-86-6
PubChem 50895 91743 50896 23681922
Molecular formula C 15 H 11 ClF 3 NO 4 C 19 H 19 ClF 3 NO 5 C 16 H 13 ClF 3 NO 4 C 15 H 10 ClF 3 NNaO 4
Molar mass 361.70 g mol −1 433.81 g mol −1 375.73 g mol −1 383.68 g mol −1
Physical state firmly liquid
Brief description colorless solid White to yellowish solid with a slightly aromatic odor
Melting point 107-108 ° C 58-61 ° C
boiling point > 280 ° C
solubility insoluble in water
GHS labeling of hazardous substances
no GHS pictograms
07 - Warning 09 - Dangerous for the environment
Caution
07 - Warning
Caution
07 - Warning 09 - Dangerous for the environment
Caution
H-phrases no 302-410 302 302-410
P-phrases no ? ? 273-501
LD 50
  • 518 mg kg −1 (rat, oral)
  • > 5000 mg kg −1 (rabbit, dermal)
  • 393 mg kg −1 (rat, oral)
  • > 5000 mg kg −1 (rabbit, dermal)
  • 337 mg kg −1 (rat, oral)

Admission status

The EU Commission decided in 2002 not to include Haloxyfop in the list of permitted active ingredients in plant protection products.

Haloxyfop-P and Haloxyfop-P-methyl have been approved as active ingredients in herbicides in the EU since January 1, 2011.

In Germany, Austria and Switzerland, pesticides containing haloxyfop-P-methyl are permitted.

Individual evidence

  1. ↑ a b Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 771 ( limited preview in Google Book search).
  2. ↑ European Commission: Review report for the active substance haloxyfop-P , October 28, 2010: It is noted that the name "haloxyfop-R" which is commonly used but has no official status, has been modified to "haloxyfop-P", the agreed ISO name of the substance.
  3. ↑ a b c d data sheet Haloxyfop-methyl from Sigma-Aldrich , accessed on November 5, 2016 ( PDF ).
  4. ↑ a b c d data sheet Haloxyfop at Sigma-Aldrich , accessed on November 5, 2016 ( PDF ).
  5. ↑ a b c d Entry on haloxyfop- (2-ethoxyethyl) in the GESTIS substance database of the IFA , accessed on August 6, 2013 (JavaScript required)
  6. ^ SD Gangolli, Royal Society of Chemistry (Great Britain): The Dictionary of Substances and Their Effects (DOSE): Volume 04 EJ . Royal Society of Chemistry, 1999, ISBN 0-85404-823-5 , pp. 544 ( limited preview in Google Book search).
  7. ↑ a b c HALOXYFOP-P-METHYL (FAO) (PDF; 391 kB).
  8. ↑ a b Data sheet Haloxyfop-P-methyl from Sigma-Aldrich , accessed on November 5, 2016 ( PDF ).
  9. ↑ Regulation (EC) No. 2076/2002 of the Commission of November 20, 2002 (PDF) extending the deadline according to Article 8 (2) of Council Directive 91/414 / EEC and on the non-inclusion of certain active substances in Annex I of this Directive and the revocation of the approval of plant protection products with these active substances.
  10. ↑ Directive 2010/86 / EU of the Commission of December 2, 2010 (PDF) amending Council Directive 91/414 / EEC to include the active ingredient Haloxyfop-P.
  11. ↑ General Directorate Health and Food Safety of the European Commission: Entry on Haloxyfop-P (Haloxyfop-R) in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved February 19, 2016.