Trifluralin (CHEM003508)

Record Information
Version1.0
Creation Date2014-08-29 06:51:46 UTC
Update Date2026-08-19 00:20:23 UTC
Accession NumberCHEM003508
Identification
Common NameTrifluralin
ClassSmall Molecule
Description
Trifluralin is a commonly used pre-emergence soil-incorporated herbicide. With about 14 million pounds used in the United States in 2001, it is one of the most widely used herbicides. 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. Its mode of action is selective and inhibits mitosis and cell division.
Contaminant Sources
  • Clean Air Act Chemicals
  • EPA Endocrine Screening
  • HPV EPA Chemicals
  • IARC Carcinogens Group 3
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amine
  • Herbicide
  • Household Toxin
  • Organic Compound
  • Organofluoride
  • Pesticide
  • Pollutant
  • Synthetic Compound
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2,6-Dinitro-N,N-dipropyl-4-(trifluoromethyl)benzenamineChEBI
alpha,alpha,alpha-Trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidineChEBI
2,6-Dinitro-N,N-dipropyl-4-trifluoromethylanilineKegg
a,a,a-Trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidineGenerator
Α,α,α-trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidineGenerator
TreflanMeSH
Chemical FormulaC13H16F3N3O4
Average Molecular Mass335.279 g/mol
Monoisotopic Mass335.109 g/mol
CAS Registry Number1582-09-8
IUPAC Name2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)aniline
Traditional Nametristar
SMILESCCCN(CCC)C1=C(C=C(C=C1[N+]([O-])=O)C(F)(F)F)[N+]([O-])=O
InChI IdentifierInChI=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
InChI KeyZSDSQXJSNMTJDA-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dinitroanilines. These are organic compounds containing an aniline moiety, which is substituted at 2 positions by a nitro group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAniline and substituted anilines
Direct ParentDinitroanilines
Alternative Parents
Substituents
  • Dinitroaniline
  • Trifluoromethylbenzene
  • Nitrobenzene
  • Nitroaromatic compound
  • Tertiary aliphatic/aromatic amine
  • Dialkylarylamine
  • C-nitro compound
  • Tertiary amine
  • Organic nitro compound
  • Organic oxoazanium
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Alkyl fluoride
  • Hydrocarbon derivative
  • Organic oxide
  • Organonitrogen compound
  • Organofluoride
  • Organopnictogen compound
  • Organohalogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Alkyl halide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Actin Filament
  • Axoneme
  • Cytoskeleton
  • Endoplasmic reticulum
  • Extracellular
  • Golgi apparatus
  • Membrane
  • Microtubule
  • Mitochondrion
  • Nuclear Membrane
  • Plasma Membrane
  • Soluble Fraction
  • Tubulin
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
Atrazine DegradationNot AvailableNot Available
Antiviral AgentsNot AvailableNot Available
Cell cycleNot Availablemap04110
Metabolic PathwaysNot AvailableNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00057 g/LALOGPS
logP5.09ALOGPS
logP4.6ChemAxon
logS-5.8ALOGPS
pKa (Strongest Basic)-1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area94.88 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity79.65 m³·mol⁻¹ChemAxon
Polarizability28.84 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (1)
Uses/SourcesThis is a man-made compound that is used as a pesticide.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0259211
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTrifluralin
Chemspider ID5368
ChEBI ID35027
PubChem Compound IDNot Available
Kegg Compound IDC14343
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=21544921
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24584589
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=24984475
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=25277710