Cyanazine (CHEM002778)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (13)XML
Record Information
Version1.0
Creation Date2013-04-25 07:56:50 UTC
Update Date2016-11-09 01:08:58 UTC
Accession NumberCHEM002778
Identification
Common NameCyanazine
ClassSmall Molecule
DescriptionCyanazine is sold by DuPont Chemical as Bladex, and has been in use since 1971. In the 1990s it was the fourth most widely used synthetic chemical pesticide in U.S. agriculture. Cyanazine is a triazine herbicide and is used as a pre- and post-emergent herbicide to control annual grasses and broadleaf weeds. It is used mostly on corn, some on cotton, and less than 1% on grain sorghum and wheat fallow. Cyanazine is classified by the EPA as a Restricted Use Pesticide (RUP) because of its teratogenicity and because it has been found in groundwater. Cyanazine can cause a variety of birth defects in animals over a wide range of doses. In a long-term study of rats fed cyanazine, moderate doses resulted in increased brain weights and decreased kidney weights in third generation offspring.
Contaminant Sources
  • Clean Air Act Chemicals
  • HPV EPA Chemicals
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amine
  • Herbicide
  • Nitrile
  • Organic Compound
  • Organochloride
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2-([4-Chloro-6-(ethylamino)-1,3,5-triazin-2-yl]amino)-2-methylpropanenitrileChEBI
2-[[4-Chloro-6-(ethylamino)-S-triazin-2-yl]amino]-2-methylpropionitrileChEBI
2-Chloro-4-(1-cyano-1-methylethylamino)-6-ethylamine-1,3,5-triazineChEBI
2-Chloro-4-(1-cyano-1-methylethylamino)-6-ethylamino-1,3,5-triazineChEBI
BladexChEBI
FortrolChEBI
2-Chloro-4-(1-cyano-1-methylethylamino)-6-ethylamino-S-triazineMeSH
Bladex 80WMeSH
Chemical FormulaC9H13ClN6
Average Molecular Mass240.693 g/mol
Monoisotopic Mass240.089 g/mol
CAS Registry Number21725-46-2
IUPAC Name2-{[4-chloro-6-(ethylimino)-1,6-dihydro-1,3,5-triazin-2-yl]amino}-2-methylpropanenitrile
Traditional Namepayze
SMILESCCNC1=NC(NC(C)(C)C#N)=NC(Cl)=N1
InChI IdentifierInChI=1S/C9H13ClN6/c1-4-12-7-13-6(10)14-8(15-7)16-9(2,3)5-11/h4H2,1-3H3,(H2,12,13,14,15,16)
InChI KeyMZZBPDKVEFVLFF-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as aminotriazines. These are organic compounds containing an amino group attached to a triazine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTriazines
Sub ClassAminotriazines
Direct ParentAminotriazines
Alternative Parents
Substituents
  • Amino-1,3,5-triazine
  • Chloro-s-triazine
  • Halo-s-triazine
  • Aminotriazine
  • Secondary aliphatic/aromatic amine
  • Aryl chloride
  • Aryl halide
  • 1,3,5-triazine
  • Heteroaromatic compound
  • Azacycle
  • Nitrile
  • Carbonitrile
  • Secondary amine
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological RolesNot Available
Chemical Roles
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.03 g/LALOGPS
logP1.29ALOGPS
logP1.14ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)8.93ChemAxon
pKa (Strongest Basic)3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area84.93 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity61.75 m³·mol⁻¹ChemAxon
Polarizability24.15 ųChemAxon
Number of Rings1ChemAxon
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, Positivesplash10-01ta-6980000000-4b8733d4472817ccad42Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-01ox-0090000000-8e03c608e4ecfaf90c13Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-0006-0090000000-6585794cbc4e543c9b8fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-03di-2590000000-1b39858946aacd149e6aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-0jc1-7920000000-91acdf98c918dd96d9e7Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-03di-0090000000-57d11e5613637c38c03dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-0jc1-7920000000-99290c625657c9533c84Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-03di-0190000000-9f60c6ecd3fc6d946951Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-03di-5970000000-7141fe81147ff1a63c72Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-0v5a-9500000000-e2336b781a7a957b816bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-0gb9-9300000000-13a9aa91a7106cfda850Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0006-0090000000-a3de9283c64520eb53e2Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0006-0090000000-1e78b34c1fd0a000adcdSpectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-0006-0090000000-073d815bfb9db5aeffadSpectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-0006-0090000000-a738ecc79bbaa09be430Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-0v59-8910000000-cff2df92578552876df5Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-0uxr-9600000000-f88dd60d34c00e4ba488Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-03di-0090000000-81ecbd9903caeea91ff8Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-03di-5980000000-fe5a8d18a929a2307e75Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-03di-0190000000-81f9ceb53cf7a047ca73Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0190000000-35f8bb8e2a252c70713bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0229-3960000000-40891c255a6257a699faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02tc-9500000000-970af82793125916dbe5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1920000000-d9833e00e48ea55b834aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dr-3390000000-fd6a4d009a0df25e5e11Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0v0u-4900000000-b8b87e43799e4fdc1e2aSpectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9730000000-6bb19a043467c779e47fSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityOrganic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (2)
MetabolismOrganic nitriles are converted into cyanide ions through the action of cytochrome P450 enzymes in the liver. Cyanide is rapidly absorbed and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (1)
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 IDHMDB0250604
FooDB IDFDB097412
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCyanazine
Chemspider ID28552
ChEBI ID38069
PubChem Compound ID30773
Kegg Compound IDC14299
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=16882534
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23762632
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=24607126
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=24631619