Flumioxazin (CHEM002808)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (4)XML
Record Information
Version1.0
Creation Date2013-04-25 07:56:51 UTC
Update Date2026-03-31 18:41:58 UTC
Accession NumberCHEM002808
Identification
Common NameFlumioxazin
ClassSmall Molecule
DescriptionFlumioxazin is a broad-spectrum contact herbicide. It works by interfering with the plants’ production of chlorophyll. Treated plants will respond quickly to treatment and rapidly decompose. Flumioxazin is an N-phenylphthalimide herbicide. The mode of action in this family of herbicides is believed to be inhibition of protoporphyrinogen oxidase, an enzyme important in the synthesis of chlorophyll. Mechanistic study findings suggest that porphyrins accumulate in susceptible plants causing photosensitization, which leads to membrane lipid peroxidation. The peroxidation of membrane lipids leads to irreversible damage of membrane function and structure in susceptible plants. Treatment of soil with flumioxazin will cause susceptible emerging plants to turn necrotic and die shortly after exposure to sunlight. Flumioxazin is used on soybeans, peanuts, orchard fruits and other crops. Flumioxazin is also used to controls invasive Eurasian watermilfoil (Myriophyllum spicatum) and curlyleaf pondweed (Potamogeton crispus). Flumioxazin has been used as an agricultural chemical since 2001, and was conditionally registered for aquatic use in 2010.
Contaminant Sources
  • FooDB Chemicals
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Amine
  • Ester
  • Ether
  • Food Toxin
  • Herbicide
  • Industrial/Workplace Toxin
  • Metabolite
  • Organic Compound
  • Organofluoride
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-[7-Fluoro-3,4-dihydro-3-oxo-4-(2-propyn-1-yl)-2H-1,4-benzoxazin-6-yl]-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dioneChEBI
7-Fluoro-6-(3,4,5,6-tetrahydrophthalimido)-4-(2-propynyl)-1,4-benzoxazin-3(2H)-oneChEBI
FlumioxazineChEBI
N-(7-Fluoro-3,4-dihydro-3-oxo-4-prop-2-ynyl-2H-1,4-benzoxazin-6-yl)cyclohex-1-ene-1,2-dicarboxamideChEBI
S 53482ChEBI
S-53482ChEBI
SumisoyaChEBI
V 53482ChEBI
7-Fluoro-6-((3,4,5,6-tetrahydro)phthalimido)-4-(2-propynyl)-1,4-benzoxazin-3(2 H)-oneMeSH
2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-Propynyl)-2H-1,4-benzoxazin-6-yl]-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione, 9ciHMDB
EINECS annex I index 613-166-00-XHMDB
Chemical FormulaC19H15FN2O4
Average Molecular Mass354.332 g/mol
Monoisotopic Mass354.102 g/mol
CAS Registry Number103361-09-7
IUPAC Name2-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-2,3,4,5,6,7-hexahydro-1H-isoindole-1,3-dione
Traditional Nameflumioxazin
SMILESFC1=CC2=C(C=C1N1C(=O)C3=C(CCCC3)C1=O)N(CC#C)C(=O)CO2
InChI IdentifierInChI=1S/C19H15FN2O4/c1-2-7-21-15-9-14(13(20)8-16(15)26-10-17(21)23)22-18(24)11-5-3-4-6-12(11)19(22)25/h1,8-9H,3-7,10H2
InChI KeyFOUWCSDKDDHKQP-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzoxazinones. These are organic compounds containing a benzene fused to an oxazine ring (a six-member aliphatic ring with four carbon atoms, one oxygen atom, and one nitrogen atom) bearing a ketone group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzoxazines
Sub ClassBenzoxazinones
Direct ParentBenzoxazinones
Alternative Parents
Substituents
  • Benzoxazinone
  • Isoindolone
  • Benzomorpholine
  • Isoindole or derivatives
  • Isoindole
  • Maleimide
  • Alkyl aryl ether
  • Benzenoid
  • Oxazinane
  • Carboxylic acid imide, n-substituted
  • Aryl fluoride
  • Aryl halide
  • Carboxylic acid imide
  • Dicarboximide
  • Tertiary carboxylic acid amide
  • Pyrroline
  • Carboxamide group
  • Lactam
  • Acetylide
  • Carboxylic acid derivative
  • Oxacycle
  • Azacycle
  • Ether
  • Organopnictogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point201 - 204°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.04 g/LALOGPS
logP1.49ALOGPS
logP1.48ChemAxon
logS-4ALOGPS
pKa (Strongest Basic)1.03ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area66.92 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity89.82 m³·mol⁻¹ChemAxon
Polarizability35.26 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-2229000000-32c923cc633219172e19Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a4i-0009000000-26962ff1f0644b52b12bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a4i-0139000000-93276620179efce4b5e7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-002b-0492000000-49b95b5bc48666c9c228Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-054k-1790000000-717403caa055caeacff6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-056s-2950000000-02b76ac5ce474ced3c25Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-004j-2920000000-68313614e41e1a80d621Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-056s-2950000000-0fea113b9a51b882b9f1Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-002b-0493000000-7857f40b5ab219cbe59cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0a4i-0029000000-9e51cb66088cbb284ef2Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-054k-1790000000-347bf9226aaccd9e8ef4Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-0a4i-0009000000-73230d0372d846edb610Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0009000000-8cb9abb7e0166e49492dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0019000000-c2694aa73d4fea59fe8cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-052b-0970000000-82617b5b2416cb07c2afSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0571-0389000000-68f3b4114e09544e4177Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0571-0389000000-81b9a8afc74ebf0f2a5aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0009000000-41dafd7e5a62dfd4c4a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0009000000-c77a6a61460302faadecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zi3-9052000000-8c9da79be6f8c4266e63Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-b5d8e7788e2b600ac517Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-2209000000-c8f318a2ae67ec9aceb6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f6x-9000000000-28e167ab494cbd513382Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-fe9f13447119f2379d38Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0009000000-fe3f7691feea3509d556Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4u-4269000000-a4dae5a303f9418130f2Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
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
DrugBank IDNot Available
HMDB IDHMDB0034854
FooDB IDFDB013420
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID83443
ChEBI ID8939
PubChem Compound ID92425
Kegg Compound IDC11035
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=24391081
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24753331
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=25475126
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=26594468
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=27108479
6.
7.
8. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.