Trifluralin

Trifluralin[1]
Names
Preferred IUPAC name
2,6-Dinitro-N,N-dipropyl-4-(trifluoromethyl)aniline
Other names
Treflan; α,α,α-trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.014.936 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C13H16F3N3O4/c1-3-5-17(6-4-2)12-10(18(20)21)7-9(13(14,15)16)8-11(12)19(22)23/h7-8H,3-6H2,1-2H3 checkY
    Key: ZSDSQXJSNMTJDA-UHFFFAOYSA-N checkY
  • InChI=1/C13H16F3N3O4/c1-3-5-17(6-4-2)12-10(18(20)21)7-9(13(14,15)16)8-11(12)19(22)23/h7-8H,3-6H2,1-2H3
    Key: ZSDSQXJSNMTJDA-UHFFFAOYAB
  • [O-][N+](=O)c1cc(cc([N+]([O-])=O)c1N(CCC)CCC)C(F)(F)F
Properties
C13H16F3N3O4
Molar mass 335.283 g·mol−1
Appearance Yellow crystals
Density 1360 kg/m3 [2]
Melting point 46 to 47 °C (115 to 117 °F; 319 to 320 K)
Boiling point 139 to 140 °C (282 to 284 °F; 412 to 413 K) (at 4.2 mmHg)
0.0024 g/100 mL
Solubility in acetone >1000 g/L[2]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Toxic to aquatic life
Lethal dose or concentration (LD, LC):
>5000 mg/kg (rat, oral)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Trifluralin is a common pre-emergent selective herbicide, a dinitroaniline. With about 14 million pounds (6,400 t) used in the United States in 2001,[3] and 3–7 million pounds (1,400–3,200 t) in 2012,[4] it is one of the most widely used herbicides. Trifluralin is also used in Australia,[5] and New Zealand,[6] previously in the EU. Introduced in 1964, Trifluralin was the first organofluorine compound used as an agrochemical.[7]

Trifluralin is generally applied to the soil to control annual grass and broadleaf weed species. It inhibits root development by interrupting mitosis and controls weeds as they germinate.[5][8] Trifluralin moves very little inside the plant, remaining in the roots.[9]

Technical grade trifluralin crystals
  1. ^ Merck Index, 11th Edition, 9598.
  2. ^ a b Tomlin, Clive (1994). The Pesticide Manual Incorporating the Agrochemicals Handbook (Tenth ed.). State Library of Western Australia: The Royal Society of Chemistry. p. 1025. ISBN 0-948404-79-5.
  3. ^ 2000-2001 Pesticide Market Estimates, United States Environmental Protection Agency
  4. ^ "Pesticides Industry Sales and Usage 2008 – 2012 Market Estimates" (PDF).
  5. ^ a b Cite error: The named reference 4f leaflet was invoked but never defined (see the help page).
  6. ^ "Application for Approval to Import or Manufacture GF-1981 for Release" (PDF). 24 Mar 2010.
  7. ^ Cite error: The named reference 50 year discovery was invoked but never defined (see the help page).
  8. ^ Grover, Raj; Wolt, Jeffrey D.; Cessna, Allan J.; Schiefer, H. Bruno (1997). "Environmental Fate of Trifluralin". Reviews of Environmental Contamination and Toxicology. Vol. 153. pp. 1–64. doi:10.1007/978-1-4612-2302-3_1. ISBN 978-1-4612-7492-6. PMID 9380893.
  9. ^ Moreland, D. E.; Farmer, F. S.; Hussey, G. G. (1 October 1972). "Inhibition of photosynthesis and respiration by substituted 2,6-dinitroaniline herbicides: I. Effects on chloroplast and mitochondrial activities". Pesticide Biochemistry and Physiology. 2 (3): 342–353. Bibcode:1972PBioP...2..342M. doi:10.1016/0048-3575(72)90039-9.