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Names | |
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IUPAC name N-(2,4-difluorophenyl)-2-[3-(trifluoromethyl)phenoxy]pyridine-3-carboxamide | |
Other names N-(2,4-Difluorophenyl)-2-(3-(trifluoromethyl)phenoxy)nicotinamide | |
Identifiers | |
ChemSpider | |
ECHA InfoCard | 100.122.360 |
PubChem CID | |
CompTox Dashboard (EPA) | |
Properties | |
C19H11F5N2O2 | |
Molar mass | 394.301 g·mol−1 |
Appearance | White Powder |
Density | 1.438 g/cm3 [1] |
Melting point | 160 [2] [1] °C (320 °F; 433 K) |
Boiling point | 376 [1] °C (709 °F; 649 K) |
Insoluble [2] | |
Solubility in acetone | Soluble [2] |
Solubility in ethylene glycol | Soluble [3] |
Solubility in ethanol | Soluble [3] |
Hazards | |
GHS labelling: | |
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H411, H413 [4] | |
P262, P273, P352, P391 [4] | |
Flash point | 181.3°C, 358.3°F [1] |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose) | >5000 mg/kg (rat, oral) [2] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Diflufenican (sometimes called DFF) 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, [5] Europe, and in Feb 2024 registered in North America by the PMRA, EPA registration pending, for use on soybean and corn. [6]
Diflufenican was discovered with a common intermediate method (CIM), [7] and trialled in England and France between 1981-1983. [8] A simple intermediate is reacted and recombined. Diflufenican derives from 2-chloronicotinic acid, one product replaced the chlorine with a phenoxy group, one receives an aniline group, and then both are recombined into DFF. [7]
The Australian Acceptable Daily Intake for diflufenican is set at 0.2 mg/kg/day, based on the NOEL of 16.3 mg/kg/day. [4] With an oral rat LD50 of >5000 mg/kg, diflufenican is not toxic to mammals, [2] nor to honeybees. [6]
Diflufenican has high persistence in soil but has low mobility, and low bioaccumulative potential. It is toxic to aquatic life. [4]
Targeted weeds display bleaching and chlorotic spotting, followed by pink and purple foliage and necrosis. Symptoms typically begin 3–4 days after application. [5] DFF's residual activity may last 8 weeks. [9]
Diflufenican inhibits carotenoid synthesis, without which photosynthesis begins to fail and the plant is vulnerable to damage from sunlight, causing growth cessation and necrosis. [6]
Diflufenican has shown control over: wild radish, wild turnip, turnip weed, [5] multiply herbicide resistant waterhemp [6] (applied pre-emergence), hedge mustard, Indian hedge mustard, charlock, deadnettle, prickly lettuce, pheasant's eye, [9] Galium aparine , ivy-leaved speedwell and Veronica persica ; [8] and suppression of capeweed, crassula, night-scented stock, marshmallow, corn gromwell, chickweed, hyssop loosestrife, Skeleton weed, speedwell, amsinckia, Paterson's curse, rough poppy, sorrel, toad rush, stinging nettle and shepherd's purse. [9]
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.
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.
Atrazine is a chlorinated herbicide of the triazine class. It is used to prevent pre-emergence broadleaf weeds in crops such as maize (corn), soybean and sugarcane and on turf, such as golf courses and residential lawns. Atrazine's primary manufacturer is Syngenta and it is one of the most widely used herbicides in the United States, Canadian, and Australian agriculture. Its use was banned in the European Union in 2004, when the EU found groundwater levels exceeding the limits set by regulators, and Syngenta could not show that this could be prevented nor that these levels were safe.
The mustard plant is any one of several plant species in the genera Brassica, Rhamphospermum and Sinapis in the family Brassicaceae. Mustard seed is used as a spice. Grinding and mixing the seeds with water, vinegar, or other liquids creates the yellow condiment known as prepared mustard. The seeds can also be pressed to make mustard oil, and the edible leaves can be eaten as mustard greens. Many vegetables are cultivated varieties of mustard plants; domestication may have begun 6,000 years ago.
Diquat is the ISO common name for an organic dication that, as a salt with counterions such as bromide or chloride is used as a contact herbicide that produces desiccation and defoliation. Diquat is no longer approved for use in the European Union, although its registration in many other countries including the USA is still valid.
Phenoxy herbicides are two families of chemicals that have been developed as commercially important herbicides, widely used in agriculture. They share the part structure of phenoxyacetic acid.
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.
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."
Sulfentrazone is the ISO common name for an organic compound used as a broad-spectrum herbicide. It acts by inhibiting the enzyme protoporphyrinogen oxidase. It was first marketed in the US in 1997 by FMC Corporation with the brand name Authority.
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.
Saflufenacil 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 weeds in crops including soybeans and corn.
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.
2,4-Dichlorophenoxyacetic acid is an organic compound with the chemical formula Cl2C6H3OCH2CO2H. It is usually referred to by its ISO common name 2,4-D. It is a systemic herbicide that kills most broadleaf weeds by causing uncontrolled growth, but most grasses such as cereals, lawn turf, and grassland are relatively unaffected.
4-Hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors are a class of herbicides that prevent growth in plants by blocking 4-Hydroxyphenylpyruvate dioxygenase, an enzyme in plants that breaks down the amino acid tyrosine into molecules that are then used by plants to create other molecules that plants need. This process of breakdown, or catabolism, and making new molecules from the results, or biosynthesis, is something all living things do. HPPD inhibitors were first brought to market in 1980, although their mechanism of action was not understood until the late 1990s. They were originally used primarily in Japan in rice production, but since the late 1990s have been used in Europe and North America for corn, soybeans, and cereals, and since the 2000s have become more important as weeds have become resistant to glyphosate and other herbicides. Genetically modified crops are under development that include resistance to HPPD inhibitors. There is a pharmaceutical drug on the market, nitisinone, that was originally under development as an herbicide as a member of this class and is used to treat an orphan disease, type I tyrosinemia.
Fomesafen is the ISO common name for an organic compound used as an herbicide. It acts by inhibiting the enzyme protoporphyrinogen oxidase (PPO) which is necessary for chlorophyll synthesis. Soybeans naturally have a high tolerance to fomesafen, via metabolic disposal by glutathione S-transferase. As a result, soy is the most common crop treated with fomesafen, followed by other beans and a few other crop types. It is not safe for maize/corn or other Poaceae.
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.
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.
Isoxaflutole is a selective herbicide used mainly in maize crops. It inhibits the enzyme 4-hydroxyphenylpyruvate dioxygenase (HPPD) and is sold under brand names including Balance and Merlin. It was first marketed by Rhône-Poulenc in 1996.
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.
Isoproturon 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.