Diflufenican

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Diflufenican
Diflufenican.svg
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 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
Properties
C19H11F5N2O2
Molar mass 394.301 g·mol−1
AppearanceWhite 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:
GHS-pictogram-pollu.svg [5]
H411, H413 [5]
P262, P273, P352, P391 [5]
Flash point 181.3°C, 358.3°F [1]
Lethal dose or concentration (LD, LC):
>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]

Contents

376 tonnes of diflufenican active ingredient were used in the United Kingdom in 2020. [8]

Discovery

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]

Toxicology

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]

Environmental Fate

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]

Effect and Mechanism

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]

Regulations

Diflufenican is registered in the United Kingdom and the European Union, for professional and amateur use. [13]

Applications

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]

List of Targetted Weeds

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]

List of Co-used Pesticides

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]

List of Crops Applied On

Diflufenican has been applied to crops, including: wheat, barley, [3] field peas, lentils, lupins and oilseed poppy. [11]

Tradenames

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">Triclopyr</span> Chemical compound used as a herbicide

Triclopyr is an organic compound in the pyridine group that is used as a systemic foliar herbicide and fungicide.

<span class="mw-page-title-main">Atrazine</span> Herbicide

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.

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

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.

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

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.

<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">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">Saflufenacil</span> Chemical compound

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.

<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.

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.

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

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.

<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">Cyanazine</span> Chemical compound

Cyanazine is a herbicide that belongs to the group of triazines. Cyanazine inhibits photosynthesis and is therefore used as a herbicide.

<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">Isoxaflutole</span> Chemical compound

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.

<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">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.

References

  1. 1 2 3 4 "Diflufenican Safety Data Sheets". EChemi.
  2. 1 2 3 4 5 "Diflufenican Standard SDS" (PDF). FujiFilm. Retrieved 7 August 2024.
  3. 1 2 3 4 5 6 7 8 9 10 Tomlin, Clive (1994). The Pesticide Manual Incorporating the Agrochemicals Handbook (Tenth ed.). State Library of Western Australia: The Royal Society of Chemistry. p. 335. ISBN   0-948404-79-5.
  4. 1 2 Li, Wentian; Wang, Juan; Li, Shuguang; Liu, Yinping; Li, Siqi; Wu, Junfeng (2023). "Solubility modeling, dissolution and solvation thermodynamics, and solute–solvent interactions of diflufenican in aqueous aprotic and protic cosolvents". The Journal of Chemical Thermodynamics. 179: 106981. doi:10.1016/j.jct.2022.106981.
  5. 1 2 3 4 5 "4Farmers Diflufenican 500 SDS" (PDF). 4Farmers Australia.
  6. 1 2 3 4 "4Farmer Diflufenican 500 Infosheet" (PDF). 4Farmers Australia.
  7. 1 2 3 4 Soltani, Nader; Willemse, Christian; Sikkema, Peter H. (3 June 2024). "Biologically effective dose of diflufenican applied preemergence for the control of multiple herbicide-resistant waterhemp in corn" (pre-proof). Weed Technology. doi: 10.1017/wet.2024.42 .
  8. "PESTICIDE USAGE SURVEY REPORT 295: ARABLE CROPS IN THE UNITED KINGDOM 2020" (PDF). Land Use & Sustainability Team.
  9. 1 2 Changling, Liu; Guan, Aiying; Yang, Jindong (17 December 2014). "Efficient Approach To Discover Novel Agrochemical Candidates: Intermediate Derivatization Method". Journal of Agricultural and Food Chemistry. 64 (1). doi:10.1021/jf5054707.
  10. 1 2 Cramp, Michael C.; Gilmour, James; Hatton, Leslie R.; Hewett, Richard H.; Duck, Donald; Nolan, Christopher J.; Parnell, Edgar W. (30 Oct 1985). "Design and Synthesis of N-(2,4-difluoropheny1)-2-(3-trifluoromethylphenoxy)-3-pyridinecarboxamide (diflufenican), a Novel Pre- and Early Post-emergence Herbicide for Use in Winter Cereals". Pesticide Science. 18: 15–28. doi:10.1002/ps.2780180103.
  11. 1 2 3 4 5 6 "4Farmers Diflufenican 500 Label" (PDF). 4Farmers Australia. Retrieved 7 August 2024.
  12. "Australia Herbicide Classification Lookup". Herbicide Resistance Action Committee.
  13. "Agency Opinion on the classification and labelling of diflufenican (ISO)" (PDF). www.hse.gov.uk. United Kingdom Health and Safety Executive. June 2022. Retrieved 13 September 2024.
  14. "4Farmers Bromoxynil DFF Label" (PDF). 4farmers.com.au. 4Farmers Australia. Retrieved 28 August 2024.
  15. Impey, Louise (2015). "How agchem firms are breathing new life into old pesticide actives". Farmers Weekly.