Trifluralin

Trifluralin[1]
IUPAC name 2,6-Dinitro-N,N-dipropyl-4-(trifluoromethyl)aniline
Identifiers
CAS number	1582-09-8 Y
PubChem	5569
ChemSpider	5368 Y
UNII	C8BX46QL7K Y
KEGG	C14343 Y
ChEMBL	CHEMBL31970 Y
Jmol-3D images	{{#if:[O-][N+](=O)c1cc(cc([N+]([O-])=O)c1N(CCC)CCC)C(F)(F)F|Image 1
SMILES [O-][N+](=O)c1cc(cc([N+]([O-])=O)c1N(CCC)CCC)C(F)(F)F
InChI 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 Y Key: ZSDSQXJSNMTJDA-UHFFFAOYSA-N Y 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
Properties
Molecular formula	C13H16F3N3O4
Molar mass	335.28 g/mol
Appearance	Yellow crystals
Melting point	46-47 °C
Boiling point	139-140 °C (@ 4.2 mmHg)
Solubility in water	0.0024 g/100 mL
Hazards
LD50	500 mg/kg (rat, oral)
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Trifluralin is a commonly used pre-emergence herbicide. With about 14 million pounds used in the United States in 2001, it is one of the most widely used herbicides.^[2] Trifluralin is generally applied to the soil to provide control of a variety of annual grass and broadleaf weed species. It inhibits root development by interrupting mitosis, and thus can control weeds as they germinate.^[3]

Trifluralin has been banned in the European Union since 20 March 2008, primarily due to its high toxicity to fish and other aquatic life.^[4]

Environmental behavior

Trifluralin undergoes an extremely complex fate in the environment and is transiently transformed into many different products as it degrades, ultimately being incorporated into soil-bound residues or converted to carbon dioxide (mineralized). Among the more unusual behaviors of trifluralin is inactivation in wet soils. This has been linked to transformation of the herbicide by reduced soil minerals, which in turn had been previously reduced by soil microorganisms as electron acceptors in the absence of oxygen. This environmental process has been reported for many structurally related herbicides (dinitroanilines) as well as a variety of energetic compounds (explosives).^[5]

References