Trifluralin

Trifluralin[1]
Names
	IUPAC name 2,6-Dinitro-N,N-dipropyl-4-(trifluoromethyl)aniline
Identifiers
CAS Number	1582-09-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:35027 ;
ChEMBL	ChEMBL31970 ;
ChemSpider	5368 ;
ECHA InfoCard	100.014.936
KEGG	C14343 ;
PubChem CID	5569;
UNII	C8BX46QL7K ;
CompTox Dashboard (EPA)	DTXSID4021395 ;
	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 Key: ZSDSQXJSNMTJDA-UHFFFAOYSA-N ; 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;
	SMILES [O-][N+](=O)c1cc(cc([N+]([O-])=O)c1N(CCC)CCC)C(F)(F)F;
Properties
Chemical formula	C13H16F3N3O4
Molar mass	335.28 g/mol
Appearance	Yellow crystals
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)
Solubility in water	0.0024 g/100 mL
Hazards
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	>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).
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	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 high toxicity to 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 using them as electron acceptors in the absence of oxygen. This environmental degradation process has been reported for many structurally related herbicides (dinitroanilines) as well as a variety of explosives like TNT and picric acid.[5]

References

Merck Index, 11th Edition, 9598.
2000-2001 Pesticide Market Estimates, United States Environmental Protection Agency
Grover, R., J.D. Wolt, A.J. Cessna, and H.B. Schiefer. 1997. Environmental fate of trifluralin. Reviews of Environmental Contamination and Toxicology 153: 65-90.
http://archive.pic.int/CH/Demo/embed/view_displayFRA.php?id=1186&back=viewB_FRAchems.php?sort=chemical European Union - Final Regulatory Action
Tor, J., C. Xu, J. M. Stucki, M. Wander, G. K. Sims. 2000. Trifluralin degradation under micro-biologically induced nitrate and Fe(III) reducing conditions. Env. Sci. Tech. 34:3148-3152.

External links

Trifluralin in the Pesticide Properties DataBase (PPDB)

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[1] Merck Index, 11th Edition, 9598.

[2] 2000-2001 Pesticide Market Estimates, United States Environmental Protection Agency

[3] Grover, R., J.D. Wolt, A.J. Cessna, and H.B. Schiefer. 1997. Environmental fate of trifluralin. Reviews of Environmental Contamination and Toxicology 153: 65-90.

[4] ttp://archive.pic.int/CH/Demo/embed/view_displayFRA.php?id=1186&back=viewB_FRAchems.php?sort=chemical European Union - Final Regulatory Action

[5] Tor, J., C. Xu, J. M. Stucki, M. Wander, G. K. Sims. 2000. Trifluralin degradation under micro-biologically induced nitrate and Fe(III) reducing conditions. Env. Sci. Tech. 34:3148-3152.