Oxyfluorfen

Oxyfluorfen is a chemical compound used as an herbicide. It is manufactured by Dow AgroSciences, Adama Agricultural Solutions and 4Farmers under the trade names Goal, Galigan, and Oxyfluorfen 240. Oxyfluorfen is used to control broadleaf and grassy weeds in a variety of nut, tree fruit, vine, and field crops, especially wine grapes and almonds. It is also used for residential weed control.

Oxyfluorfen

Names
IUPAC name 2-chloro-1-(3-ethoxy-4-nitrophenoxy)-4-(trifluoromethyl)benzene
Other names Oxyfluorfen; Oxyfluorofen; 2-chloro-1-(3-ethoxy-4-nitrophenoxy)-4-trifluoromethylbenzene; 2-chloro-α,α,α-trifluoro-p-tolyl-3-ethoxy-4-nitrophenyl ether; Galigan; Goal; Goldate; Oxyfluorfene; Oxygold; Zoomer
Identifiers
CAS Number	42874-03-3
3D model (JSmol)	Interactive image
ChEBI	CHEBI:82029
ChEMBL	ChEMBL1871400
ChemSpider	35974
ECHA InfoCard	100.050.876
EC Number	255-983-0
KEGG	C18881
PubChem CID	39327
CompTox Dashboard (EPA)	DTXSID7024241
InChI InChI=1S/C15H11ClF3NO4/c1-2-23-14-8-10(4-5-12(14)20(21)22)24-13-6-3-9(7-11(13)16)15(17,18)19/h3-8H,2H2,1H3 Key: OQMBBFQZGJFLBU-UHFFFAOYSA-N
SMILES CCOC1=C(C=CC(=C1)OC2=C(C=C(C=C2)C(F)(F)F)Cl)[N+](=O)[O-]
Properties
Chemical formula	C15H11ClF3NO4
Molar mass	361.702 g/mol
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H410
Lethal dose or concentration (LD, LC):
LD50 (median dose)	5 g/kg (rat, oral)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Toxicity

Oxyfluorfen has low acute oral, dermal, and inhalation toxicity in humans. The primary toxic effects are in the liver and alterations in blood parameters (anemia). It is classified as a possible human carcinogen. Its LD₅₀ is over 5000 mg/kg.

Environmental impact

Oxyfluorfen is classified as an environmental hazard under the GHS due to being "very toxic to aquatic life with long lasting effects".

Oxyfluorfen is toxic to plants, invertebrates, and fish. Birds and mammals may also experience subchronic and chronic effects from oxyfluorfen. It is persistent in soil and has been shown to drift from application sites to nearby areas. It can contaminate surface water through spray drift and runoff. Oxyflurofen's waterborne LC₅₀ for trout is less than 0.5 mg/L.

Mode of action

Oxyfluorfen is a diphenyl ether herbicide and acts via inhibition of protoporphyrinogen oxidase, (destroying chlorophill production and cell membranes), making its HRAC resistance class Group G (Aus), Group E (Global) and 14 (numerical).

Oxyfluorfen suffers from poor translocation, despite rapid shoot and foliar uptake. Desiccation in affected weeds begins in hours, with necrosis and death following in days.

Application

Oxyfluorfen is used in the USA and Australia, at rates of up to 1500 g/Ha.

It has been used on crops of tree fruit, nuts, onion, tobacco, vines, almonds, apples, apricots, grapevine, macadamias, peaches, pears, pecans, plums, walnuts, Duboisia, Avocado, custard apple, kiwi fruit, Longan, Lychees, mango, Passionfruit, Pawpaw, Rambutan, Brassica crops, broccoli, cabbages, cauliflower, pyrethrum and (before sowing) cotton or winter cereals.