Oryzalin (CHEM003482)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (18)XML
Record Information
Version1.0
Creation Date2014-08-29 06:51:44 UTC
Update Date2016-11-09 01:09:09 UTC
Accession NumberCHEM003482
Identification
Common NameOryzalin
ClassSmall Molecule
DescriptionOryzalin is a pre-emergence surface-applied herbicide. It acts through the disruption (depolymerization) of microtubules, thus blocking anisotropic growth of plant cells. It is used for control of annual grasses and broad-leaved weeds in fruit trees, nut trees, vineyards, turfs and around ornamentals by selectively affecting physiological growth process. It can also be used to induce ploidity as an alternative to colchicine. It has a low aqueous solubility, is not volatile and, based on its chemical properties, is not expected to leach to groundwater. However, groundwater monitoring programmes have identified it as a pollutant. It generally tends not to be persistent in soil or water systems. It has a low mammalian toxicity and is a potential carcinogen. It is moderately toxic to birds, most aquatic organisms, honeybees and earthworms.
Contaminant Sources
  • Clean Air Act Chemicals
  • HPV EPA Chemicals
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Amine
  • Herbicide
  • Organic Compound
  • Pesticide
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
3,5-Dinitro-N(4),N(4)-dipropylsulfanilamideChEBI
3,5-Dinitro-N4,N4-dipropylsulphanilamideChEBI
4-(Dipropylamino)-3,5-dinitrobenzene-1-sulfonamideChEBI
3,5-Dinitro-N(4),N(4)-dipropylsulphanilamideGenerator
3,5-Dinitro-N4,N4-dipropylsulfanilamideGenerator
4-(Dipropylamino)-3,5-dinitrobenzene-1-sulphonamideGenerator
3,5-Dinitro-N,N-di(N-propyl)sulfanilamideMeSH
SurflanMeSH
Chemical FormulaC12H18N4O6S
Average Molecular Mass346.360 g/mol
Monoisotopic Mass346.095 g/mol
CAS Registry Number19044-88-3
IUPAC Name4-(dipropylamino)-3,5-dinitrobenzene-1-sulfonamide
Traditional Nameoryzalin
SMILESCCCN(CCC)C1=C(C=C(C=C1[N+]([O-])=O)S(N)(=O)=O)[N+]([O-])=O
InChI IdentifierInChI=1S/C12H18N4O6S/c1-3-5-14(6-4-2)12-10(15(17)18)7-9(23(13,21)22)8-11(12)16(19)20/h7-8H,3-6H2,1-2H3,(H2,13,21,22)
InChI KeyUNAHYJYOSSSJHH-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
  • Aminobenzenesulfonamide
  • Benzenesulfonamide
  • Nitrobenzene
  • Benzenesulfonyl group
  • Nitroaromatic compound
  • Dialkylarylamine
  • Tertiary aliphatic/aromatic amine
  • Organosulfonic acid amide
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Sulfonyl
  • Aminosulfonyl compound
  • C-nitro compound
  • Organic nitro compound
  • Tertiary amine
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organic oxoazanium
  • Allyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organosulfur compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Organic zwitterion
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Actin Cytoskeleton
  • Actin Filament
  • Axoneme
  • Cell surface
  • Centriole
  • Cytoskeleton
  • Cytosol
  • Endoplasmic reticulum
  • Extracellular
  • Extracellular matrix
  • Golgi apparatus
  • Kinetochore
  • Membrane
  • Membrane Fraction
  • Microtubule
  • Mitochondrion
  • Nuclear Membrane
  • Nucleoplasm
  • Peroxisome
  • Plasma Membrane
  • Soluble Fraction
  • Tubulin
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
Flagellar AssemblyNot AvailableNot Available
Dna replicationNot Availablemap03030
Cell cycleNot Availablemap04110
EndocytosisNot Availablemap04144
Applications
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 Solubility0.016 g/LALOGPS
logP2.42ALOGPS
logP2.33ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)9.9ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area155.04 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity85.84 m³·mol⁻¹ChemAxon
Polarizability32.44 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-1009000000-5c020701dd7cdbc72d31Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-2009000000-4c5b1d8d30b7f6470b0dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-f4b5a722eecdd2ba5863Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-1b918909535479b5635cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0009000000-da97a7a3a352fe08d8e6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0036-9022000000-00cde0f4d788f4e678f9Spectrum
MSMass Spectrum (Electron Ionization)splash10-016r-5389000000-78252d08e971552a904aSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)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 IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkOryzalin
Chemspider IDNot Available
ChEBI ID73163
PubChem Compound ID29393
Kegg Compound IDC18877
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=20405146
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20870876
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21983568
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22771930
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23261650