Diflufenican

Last updated
Diflufenican
Diflufenican.svg
Names
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 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]
Solubility in acetone Soluble [2]
Solubility in ethylene glycol Soluble [3]
Solubility in ethanol Soluble [3]
Hazards
GHS labelling:
GHS-pictogram-pollu.svg [4]
H411, H413 [4]
P262, P273, P352, P391 [4]
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, [5] Europe, and in Feb 2024 registered in North America by the PMRA, EPA registration pending, for use on soybean and corn. [6]

Contents

Discovery

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]

Safety & Environment

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]

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. [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]

List of Controlled Weeds

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]

Trade Names

Related Research Articles

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

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

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

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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 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.
  4. 1 2 3 4 5 "4Farmers Diflufenican 500 SDS" (PDF). 4Farmers Australia.
  5. 1 2 3 "4Farmer Diflufenican 500 Infosheet" (PDF). 4Farmers Australia.
  6. 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 .
  7. 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.
  8. 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.
  9. 1 2 3 "4Farmers Diflufenican 500 Label" (PDF). 4Farmers Australia. Retrieved 7 August 2024.