Names | |
---|---|
IUPAC name N-(2,4-difluorophenyl)-2-[3-(trifluoromethyl)phenoxy]pyridine-3-carboxamide | |
Other names diflufenicanil; 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] – 0.05mg/L [3] | |
Solubility in acetone | Soluble [2] – 100 g/L [3] |
Solubility in ethylene glycol | Soluble [4] |
Solubility in ethanol | Soluble [4] |
Vapor pressure | 0.07 mPa (30°C) [3] |
Hazards | |
GHS labelling: | |
[5] | |
H411, H413 [5] | |
P262, P273, P352, P391 [5] | |
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, [6] Europe, and in Feb 2024 registered in North America by the PMRA, EPA registration pending, for use on soybean and corn. [7]
376 tonnes of diflufenican active ingredient were used in the United Kingdom in 2020. [8]
Diflufenican was discovered with a common intermediate method (CIM), [9] and trialled in England and France between 1981 and 1983. [10] 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. [9]
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. [5] With an oral rat LD50 of >5000 mg/kg, diflufenican is not toxic to mammals, [2] nor to honeybees. [7] [3]
By inhalation, the air LC50 is 2.34 mg/L, for rats. It is not irritating to the skin and eyes, tested on rabbits. In dogs over 90 days, a NOEL of 1000 mg/kg daily was found. By the Ames Test, it is non-mutagenic. [3]
To birds, diflufenican is not toxic. LD50 of >2150 mg/kg (quail), >4000 mg/kg (mallard ducks). For fish, the LC50 is 56–100 mg/L (rainbow trout), 105 mg/L (carp). DFF does not inhibit the growth of algae. Non-toxic to earthworms. [3]
Diflufenican has high persistence in soil but has low mobility, and low bioaccumulative potential. It is toxic to aquatic life. [5] (See toxicology section for details).
Diflufenican rapidly metabolises in cereals to carbon dioxide via nicotinamide and nicotinic acid, and leaves no detectable residue after 200–250 days. In soil, similar degradation to CO2 is seen, with a half life of 15 to 30 weeks. [3]
Targeted weeds display bleaching and chlorotic spotting, followed by pink and purple foliage and necrosis. Symptoms typically begin 3–4 days after application. [6] DFF's residual activity may last 8 weeks. [11]
Diflufenican inhibits carotenoid synthesis, without which photosynthesis begins to fail and the plant is vulnerable to damage from sunlight, causing growth cessation and necrosis. [7] It is absorbed by germinating seedlings. Usually applied at 125–250 g/ha pre-emergence or shortly after, often with other cereal herbicides. [3]
Diflufenican is a Group F, (Australia), F1 (global) or Group 12 (numeric) resistance class herbicide. [12]
Diflufenican is registered in the United Kingdom and the European Union, for professional and amateur use. [13]
Diflufenican is often applied at 50–100 g/ha, [11] [6] or lower if part of a herbicide mixture, e.g. as little as 9 g/ha with bromoxynil. [14]
Diflufenican has shown control over: wild radish, wild turnip, turnip weed, [6] multiply herbicide resistant waterhemp [7] (applied pre-emergence), hedge mustard, Indian hedge mustard, charlock, deadnettle, prickly lettuce, pheasant's eye, [11] Galium aparine , ivy-leaved speedwell and Veronica persica ; [10] 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. [11]
Diflufenican has been sold in formulations containing (not limited to): isoproturon, ioxynil, mecoprop, bromoxynil, diclofop-methyl, [3] and pendimethalin. [15] Furthermore, compatibility is reported with: simazine, alpha cypermethrin, metribuzin and quizalofop, in addition to compatibility with most grass herbicides. [11]
Diflufenican has been applied to crops, including: wheat, barley, [3] field peas, lentils, lupins and oilseed poppy. [11]
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.
Triclopyr is an organic compound in the pyridine group that is used as a systemic foliar herbicide and fungicide.
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.
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.
Bromoxynil is an organic compound with the formula HOBr2C6H2CN. It is classified as a nitrile herbicide, and as such sold under many trade names. It is a white solid. It works by inhibiting photosynthesis. It is moderately toxic to mammals.
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.
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.
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.
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.
Imazaquin is an imidazolinone herbicide, so named because it contains an imidazolinone core. This organic compound is used to control a broad spectrum of weed species. It is a colorless or white solid, although commercial samples can appear brown or tan.
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.
Cyanazine is a herbicide that belongs to the group of triazines. Cyanazine inhibits photosynthesis and is therefore used as a herbicide.
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 (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.
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.