Fomesafen

Fomesafen
Names
Preferred IUPAC name
5-[2-Chloro-4-(trifluoromethyl)phenoxy]-N-(methanesulfonyl)-2-nitrobenzamide
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.069.470 Edit this at Wikidata
EC Number
  • 276-439-9
KEGG
UNII
  • InChI=1S/C15H10ClF3N2O6S/c1-28(25,26)20-14(22)10-7-9(3-4-12(10)21(23)24)27-13-5-2-8(6-11(13)16)15(17,18)19/h2-7H,1H3,(H,20,22)
    Key: BGZZWXTVIYUUEY-UHFFFAOYSA-N
  • CS(=O)(=O)NC(=O)C1=C(C=CC(=C1)OC2=C(C=C(C=C2)C(F)(F)F)Cl)[N+](=O)[O-]
Properties[1]
C15H10ClF3N2O6S
Molar mass 438.76 g·mol−1
50 mg/L (20 °C)
log P -1.2 (20 °C)
Acidity (pKa) 2.83
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H302
P264, P270, P301+P312, P330, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Fomesafen is the ISO common name[2] for an organic compound used as an herbicide. It acts by inhibiting the enzyme protoporphyrinogen oxidase (PPO)[3] which is necessary for chlorophyll synthesis. Soybeans naturally have a high tolerance to fomesafen,[3][4] via metabolic disposal by glutathione S-transferase.[3][4] As a result, soy is the most common crop treated with fomesafen, followed by other beans and a few other crop types.[5] It is not safe for maize/corn[6] or other Poaceae.[4]

  1. ^ Pesticide Properties Database. "Fomesafen". University of Hertfordshire. Retrieved 2021-03-03.
  2. ^ "Compendium of Pesticide Common Names: fomesafen". BCPC.
  3. ^ a b c "fomesafen". Weed Ecology and Management Laboratory at Cornell University. Retrieved 2020-11-22.
  4. ^ a b c 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.
  5. ^ "Registration Review Label Mitigation for Fomesafen" (PDF). United States Environmental Protection Agency.
  6. ^ "Fomesafen Carryover Injury to Corn". Iowa State University. 2014-06-03. Retrieved 2020-11-22.