Oxyfluorfen

Last updated
Oxyfluorfen
Oxyfluorfen.svg
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 255-983-0
KEGG
PubChem CID
  • 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]
GHS-pictogram-pollu.svg
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]

Contents

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

Environmental impact

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

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

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]

Related Research Articles

<span class="mw-page-title-main">Herbicide</span> Type of chemical used to kill unwanted plants

Herbicides, also commonly known as weed killers, are substances used to control undesired plants, also known as weeds. Selective herbicides control specific weed species while leaving the desired crop relatively unharmed, while non-selective herbicides kill plants indiscriminately. The combined effects of herbicides, nitrogen fertilizer, and improved cultivars has increased yields of major crops by 3x to 6x from 1900 to 2000.

<span class="mw-page-title-main">Glyphosate</span> Systemic herbicide and crop desiccant

Glyphosate is a broad-spectrum systemic herbicide and crop desiccant. It is an organophosphorus compound, specifically a phosphonate, which acts by inhibiting the plant enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSP). It is used to kill weeds, especially annual broadleaf weeds and grasses that compete with crops. Its herbicidal effectiveness was discovered by Monsanto chemist John E. Franz in 1970. Monsanto brought it to market for agricultural use in 1974 under the trade name Roundup. Monsanto's last commercially relevant United States patent expired in 2000.

<span class="mw-page-title-main">Paraquat</span> Chemical compound used as an herbicide

Paraquat (trivial name; ), or N,N′-dimethyl-4,4′-bipyridinium dichloride (systematic name), also known as methyl viologen, is an organic compound with the chemical formula [(C6H7N)2]Cl2. It is classified as a viologen, a family of redox-active heterocycles of similar structure. This salt is one of the most widely used herbicides. It is quick-acting and non-selective, killing green plant tissue on contact. It is also toxic (lethal) to human beings and animals due to its redox activity, which produces superoxide anions. It has been linked to the development of Parkinson's disease and is banned in 58 countries.

<span class="mw-page-title-main">Glufosinate</span> Broad-spectrum herbicide

Glufosinate is a naturally occurring broad-spectrum herbicide produced by several species of Streptomyces soil bacteria. Glufosinate is a non-selective, contact herbicide, with some systemic action. Plants may also metabolize bialaphos and phosalacine, other naturally occurring herbicides, directly into glufosinate. The compound irreversibly inhibits glutamine synthetase, an enzyme necessary for the production of glutamine and for ammonia detoxification, giving it antibacterial, antifungal and herbicidal properties. Application of glufosinate to plants leads to reduced glutamine and elevated ammonia levels in tissues, halting photosynthesis and resulting in plant death.

<span class="mw-page-title-main">Pendimethalin</span> Chemical compound

Pendimethalin is an herbicide of the dinitroaniline class used in premergence and postemergence applications to control annual grasses and certain broadleaf weeds. It inhibits cell division and cell elongation. Pendimethalin is listed in the K1-group according to the Herbicide Resistance Action Committee (HRAC) classification and is approved in Europe, North America, South America, Africa, Asia and Oceania for different crops including cereals, corn, soybeans, rice, potato, legumes, fruits, vegetables, nuts as well as lawns and ornamental plants.

<span class="mw-page-title-main">Dicamba</span> Chemical compound used as herbicide

Dicamba is a selective systemic herbicide first registered in 1967. Brand names for formulations of this herbicide include Dianat, Banvel, Diablo, Oracle and Vanquish. This chemical compound is a chlorinated derivative of o-anisic acid. It has been described as a "widely used, low-cost, environmentally friendly herbicide that does not persist in soils and shows little or no toxicity to wildlife and humans."

<span class="mw-page-title-main">Trifluralin</span> Weed control herbicide

Trifluralin is a commonly used pre-emergence selective herbicide. With about 14 million pounds (6,400 t) used in the United States in 2001, and 3–7 million pounds (1,400–3,200 t) in 2012, it is one of the most widely used herbicides. Trifluralin is also used in Australia. Introduced in 1964, Trifluralin was the first organofluorine compound used as an agrochemical.

<span class="mw-page-title-main">Weed</span> Plant considered undesirable in a particular place or situation

A weed is a plant considered undesirable in a particular situation, growing where it conflicts with human preferences, needs, or goals. Plants with characteristics that make them hazardous, aesthetically unappealing, difficult to control in managed environments, or otherwise unwanted in farm land, orchards, gardens, lawns, parks, recreational spaces, residential and industrial areas, may all be considered weeds. The concept of weeds is particularly significant in agriculture, where the presence of weeds in fields used to grow crops may cause major losses in yields. Invasive species, plants introduced to an environment where their presence negatively impacts the overall functioning and biodiversity of the ecosystem, may also sometimes be considered weeds.

<span class="mw-page-title-main">Monolinuron</span> Chemical compound

Monolinuron is a pesticide, more specifically a selective systemic herbicide and an algaecide. As an herbicide, it is used to control broad-leaved weeds and annual grasses in vegetable crops such as leeks, potatoes, and dwarf French beans. Monolinuron affects the photosynthesis in weeds. Following uptake of monolinuron through roots and leaves of weeds, monolinuron causes early symptoms of yellowing and die-back of the leaves, eventually resulting in weed death. In fishkeeping, it is used to control blanket weed and hair algae.

<span class="mw-page-title-main">Mesotrione</span> Chemical compound used as an herbicide

Mesotrione is a selective herbicide used mainly in maize crops. It is a synthetic compound inspired by the natural substance leptospermone found in the bottlebrush tree Callistemon citrinus. It inhibits the enzyme 4-hydroxyphenylpyruvate dioxygenase (HPPD) and is sold under brand names including Callisto and Tenacity. It was first marketed by Syngenta in 2001.

<span class="mw-page-title-main">Bentazon</span> Chemical compound

Bentazon is a chemical manufactured by BASF Chemicals for use in herbicides. It is categorized under the thiadiazine group of chemicals. Sodium bentazon is available commercially and appears slightly brown in colour.

<span class="mw-page-title-main">Fluazifop</span> ACCase herbicide, fop, anti-grass

Fluazifop is the common name used by the ISO for an organic compound that is used as a selective herbicide. The active ingredient is the 2R enantiomer at its chiral centre and this material is known as fluazifop-P when used in that form. More commonly, it is sold as its butyl ester, fluazifop-P butyl with the brand name Fusilade.

<span class="mw-page-title-main">Butafenacil</span> Chemical compound

Butafenacil is the ISO common name for an organic compound of the pyrimidinedione chemical class used as an herbicide. It acts by inhibiting the enzyme protoporphyrinogen oxidase to control broadleaf and some grass weeds in crops including cereals and canola.

<span class="mw-page-title-main">Bromoxynil octanoate</span> Herbicide, active ingredient

Bromoxynil octanoate is a herbicide active ingredient, closely related to bromoxynil, ioxynil, and ioxynil octanoate. Bromoxynil controls broad leafed weeds in many crops, and is used in the USA, Europe and Australia, on crops, roadsides and turf.

<span class="mw-page-title-main">Tribenuron</span> Chemical compound

Tribenuron in the form of tribenuron-methyl is a sulfonylurea herbicide. Its mode of action is the inhibition of acetolactate synthase, group 2 of the Herbicide Resistance Action Committee's classification scheme.

<span class="mw-page-title-main">Prosulfocarb</span> Weed control herbicide

Prosulfocarb is a pre-emergent herbicide used agriculturally in Australia, the EU, Morocco and Iran, for control of annual ryegrass and toad rush in wheat and barley crops. It was introduced to the EU in 1988 and is rapidly growing in use, with sales increasing by over 500% in France since 2008.

<span class="mw-page-title-main">Diflufenican</span> Weed control herbicide

Diflufenican is a herbicide used to control weeds including wild radish and wild turnip weeds or suppress capeweed, crassula, marshmallow or shepherd's purse, in clover pasture, lupins, lentils or field peas. It has seen use in Australia, Europe, and in Feb 2024 registered in North America by the PMRA, EPA registration pending, for use on soybean and corn.

<span class="mw-page-title-main">Isoproturon</span> Weed control herbicide

Isoproturon (IPU) is a urea class selective herbicide, which has been used to control annual grasses and many broad leafed weeds in wheat, barley, rye and triticale.

<span class="mw-page-title-main">Ioxynil</span> Herbicide Chemical Compound

Ioxynil is a post-emergence selective nitrile herbicide. It is used in Australia, New Zealand and Japan to control broadleaf weeds via photosynthesis inhibition. It is used notably on onion crops, among others, normally at 300–900 g/Ha. It was introduced in 1966. The supply of ioxynil is decreasing, but the herbicide remains effective.

<span class="mw-page-title-main">Ethofumesate</span> Weed control herbicide

Ethofumesate is a pre- and post-emergence herbicide used on sugar beets to control weeds, notably blackgrasses. UK registration in 2016 is planned for pre-emergence use on wheat as an auxiliary component of tank mix. Ethofumesate is used in Australia, to control wintergrasses in turfgrasses, along fencelines and tree plantations. Young weeds absorb ethofumesate through roots and shoots, and the ethofumesate inhibits respiration and photosynthesis. Ethofumesate is a Group J (Australia), K3 (Global), Group 15 (numeric), resistance class herbicide.

References

  1. 1 2 "Oxyfluorfen". PubChem . National Center for Biotechnology Information . Retrieved 18 March 2022.
  2. 1 2 3 4 5 6 7 "Oxyfluorfen RED Facts" (PDF). US EPA. October 2002.
  3. 1 2 3 "4Farmers Oxyfluorfen 240 EC Infosheet" (PDF). 4farmers.com.au. 4Farmers Australia.
  4. 1 2 "Oxyflurofen 240 EC SDS" (PDF). 4farmers.com.au. 4Farmers Australia.
  5. 1 2 "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.