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Oxyfluorfen

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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.050.876 Edit this at Wikidata
EC Number
  • 255-983-0
KEGG
  • 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
  • CCOC1=C(C=CC(=C1)OC2=C(C=C(C=C2)C(F)(F)F)Cl)[N+](=O)[O-]
Properties
C15H11ClF3NO4
Molar mass 361.702 g/mol
Hazards
GHS labelling:[1]
GHS09: Environmental hazard
Warning
H410
Lethal dose or concentration (LD, LC):
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).

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.[2][3] 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.[2]

Toxicity

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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).[2] It is classified as a possible human carcinogen.[2] Its LD50 is over 5000 mg/kg.[4]

Environmental impact

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Oxyfluorfen is classified as an environmental hazard under the GHS due to being "very toxic to aquatic life with long lasting effects".[1]

Oxyfluorfen is toxic to plants, invertebrates, and fish. Birds and mammals may also experience subchronic and chronic effects from oxyfluorfen.[2] It is persistent in soil and has been shown to drift from application sites to nearby areas.[2] It can contaminate surface water through spray drift and runoff.[2] Oxyflurofen's waterborne LC50 for trout is less than 0.5 mg/L.[4]

Mode of action

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Oxyfluorfen is a diphenyl ether herbicide and acts via inhibition of protoporphyrinogen oxidase, (destroying chlorophill production and cell membranes),[3] making its HRAC resistance class Group G (Aus),[5] Group E (Global) and 14 (numerical).[6]

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.[3]

Application

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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.[5]

References

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  1. ^ a b "Oxyfluorfen". PubChem. National Center for Biotechnology Information. Retrieved 18 March 2022.
  2. ^ a b c d e f g "Oxyfluorfen RED Facts" (PDF). US EPA. October 2002.
  3. ^ a b c "4Farmers Oxyfluorfen 240 EC Infosheet" (PDF). 4farmers.com.au. 4Farmers Australia.
  4. ^ a b "Oxyflurofen 240 EC SDS" (PDF). 4farmers.com.au. 4Farmers Australia.
  5. ^ a b "4Farmers Oxyfluorfen 240 EC Leaflet" (PDF). www.4farmers.com.au. 4Farmers Australia. Retrieved 20 September 2024.
  6. ^ "2024 HRAC GLOBAL HERBICIDE MOA CLASSIFICATION MASTER LIST". Herbicide Resistance Action Committee.