Acifluorfen

Acifluorfen
Skeletal formula
Space-filling model of acifluorfen
Names
Preferred IUPAC name
5-[2-Chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid
Identifiers
  • Compounds
  • Acid: Acifluorfen
  • Na+ salt: Acifluorfen sodium
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.051.468 Edit this at Wikidata
UNII
  • InChI=1S/C14H7ClF3NO5/c15-10-5-7(14(16,17)18)1-4-12(10)24-8-2-3-11(19(22)23)9(6-8)13(20)21/h1-6H,(H,20,21) checkY
    Key: NUFNQYOELLVIPL-UHFFFAOYSA-N checkY
  • Na+ salt: InChI=1S/C14H7ClF3NO5.Na/c15-10-5-7(14(16,17)18)1-4-12(10)24-8-2-3-11(19(22)23)9(6-8)13(20)21;/h1-6H,(H,20,21);/q;+1/p-1
    Key: RVULBHWZFCBODE-UHFFFAOYSA-M
  • Acid: Clc2cc(ccc2Oc1cc(C(=O)O)c([N+]([O-])=O)cc1)C(F)(F)F
Properties[1]
C14H7ClF3NO5
Molar mass 361.66 g·mol−1
Density 1.573 g/mL
Melting point 155 °C
250 g/L (20 °C)
log P 1.18 (20 °C)
Acidity (pKa) 3.86
Pharmacology
Legal status
  • AU: S6 (Poison)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Acifluorfen is the ISO common name[2] for an organic compound used as an herbicide. It acts by inhibiting the enzyme protoporphyrinogen oxidase which is necessary for chlorophyll synthesis. Soybeans naturally have a high tolerance to acifluorfen and its salts, via metabolic disposal by glutathione S-transferase.[3][4] It is effective against broadleaf weeds and grasses and is used agriculturally on fields growing soybeans, peanuts, peas, and rice.[5]

  1. ^ Pesticide Properties Database. "Acifluorfen". University of Hertfordshire. Retrieved 2021-03-03.
  2. ^ "Compendium of Pesticide Common Names: acifluorfen". BCPC.
  3. ^ Andrews, Christopher J.; Skipsey, Mark; Townson, Jane K.; Morris, Carol; Jepson, Ian; Edwards, Robert (1997). "Glutathione transferase activities toward herbicides used selectively in soybean". Pesticide Science. 51 (2). Wiley: 213–222. doi:10.1002/(sici)1096-9063(199710)51:2<213::aid-ps622>3.0.co;2-l. ISSN 0031-613X.
  4. ^ "Registration Review Label Mitigation for Sodium Acifluorfen" (PDF). United States Environmental Protection Agency. 2020-06-02. Retrieved 2021-03-05.
  5. ^ Acifluorfen, Extension Toxicology Network