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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:52:48 UTC
Update Date2019-07-23 06:12:09 UTC
HMDB IDHMDB0032943
Secondary Accession Numbers
  • HMDB32943
Metabolite Identification
Common NameDiazinon
DescriptionDiazinon, also known as dimpylate or new Z diazinon, belongs to the class of organic compounds known as pyrimidinyl phosphorothioates. These are organic compounds containing the thiophosphoric acid functional group or a derivative thereof, with the general structure ROP(OR')(OR'')=S, where R= pyrimidine, R' = organyl group , and R\" = any atom. Based on a literature review a small amount of articles have been published on Diazinon.
Structure
Data?1563862329
Synonyms
ValueSource
DimpylateChEBI
O,O-Diethyl 2-isopropyl-4-methylpyrimidyl-6-thiophosphateChEBI
O,O-Diethyl O-(2-isopropyl-4-methyl-6-pyrimidyl) thionophosphateChEBI
O,O-Diethyl O-(2-isopropyl-6-methyl-4-pyrimidinyl) phosphorothioateChEBI
O,O-Diethyl O-[6-methyl-2-(1-methylethyl)pyrimidin-4-yl] thiophosphateChEBI
Phosphorothioic acid, O,O-diethyl O-(6-methyl-2-(1-methylethyl)-4-pyrimidinyl) esterChEBI
New Z diazinonKegg
Optimizer insecticideKegg
Dimpylic acidGenerator
O,O-Diethyl 2-isopropyl-4-methylpyrimidyl-6-thiophosphoric acidGenerator
O,O-Diethyl O-(2-isopropyl-4-methyl-6-pyrimidyl) thionophosphoric acidGenerator
O,O-Diethyl O-(2-isopropyl-6-methyl-4-pyrimidinyl) phosphorothioic acidGenerator
O,O-Diethyl O-[6-methyl-2-(1-methylethyl)pyrimidin-4-yl] thiophosphoric acidGenerator
Phosphorothioate, O,O-diethyl O-(6-methyl-2-(1-methylethyl)-4-pyrimidinyl) esterGenerator
BazudineMeSH
NeocidolMeSH
NeotsidolMeSH
Agridin 60HMDB
Alfa-toxHMDB
AntigalHMDB
AntlakHMDB
BassadinonHMDB
BasudinHMDB
BazudenHMDB
BazudinHMDB
CiazinonHMDB
CompassHMDB
DacutoxHMDB
DassitoxHMDB
DazzelHMDB
DelzinonHMDB
DiagranHMDB
DianonHMDB
DiazideHMDB
DiazinoneHMDB
DiazitolHMDB
DiazolHMDB
DicidHMDB
Diethyl 2-isopropyl-4-methyl-6-pyrimidyl thionophosphateHMDB
Diethyl dimpylatumHMDB
Dimpylate, innHMDB
DipofeneHMDB
DisonexHMDB
DizictolHMDB
DiziktolHMDB
DizinilHMDB
DizinonHMDB
DrawizonHMDB
DyzolHMDB
EktobandHMDB
ExodinHMDB
FezudinHMDB
FlytrolHMDB
GalesanHMDB
GardentoxHMDB
Isopropylmethylpyrimidyl diethyl thiophosphateHMDB
KayazinonHMDB
KayazolHMDB
Knox-outHMDB
MeodinonHMDB
NedcidolHMDB
NeodinonHMDB
NipsanHMDB
NucidolHMDB
OleodiazinonHMDB
OptimizerHMDB
Root guardHMDB
SarolexHMDB
SpectracideHMDB
SpertacideHMDB
SrolexHMDB
TerminatorHMDB
Chemical FormulaC12H21N2O3PS
Average Molecular Weight304.346
Monoisotopic Molecular Weight304.10104975
IUPAC NameO,O-diethyl O-6-methyl-2-(propan-2-yl)pyrimidin-4-yl phosphorothioate
Traditional Namediazinon
CAS Registry Number333-41-5
SMILES
CCOP(=S)(OCC)OC1=NC(=NC(C)=C1)C(C)C
InChI Identifier
InChI=1S/C12H21N2O3PS/c1-6-15-18(19,16-7-2)17-11-8-10(5)13-12(14-11)9(3)4/h8-9H,6-7H2,1-5H3
InChI KeyFHIVAFMUCKRCQO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrimidinyl phosphorothioates. These are organic compounds containing the thiophosphoric acid functional group or a derivative thereof, with the general structure ROP(OR')(OR'')=S, where R= pyrimidine, R' = organyl group , and R\" = any atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic thiophosphoric acids and derivatives
Sub ClassThiophosphoric acid esters
Direct ParentPyrimidinyl phosphorothioates
Alternative Parents
Substituents
  • Pyrimidinyl phosphorothioate
  • Thiophosphate triester
  • Pyrimidine
  • Heteroaromatic compound
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.04 mg/mL at 25 °CNot Available
LogP3.81Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.035 g/LALOGPS
logP10(4.45) g/LALOGPS
logP10(4.19) g/LChemAxon
logS10(-3.9) g/LALOGPS
pKa (Strongest Basic)4.19ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area53.47 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity80.76 m³·mol⁻¹ChemAxon
Polarizability31.48 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+168.1631661259
DarkChem[M-H]-168.22831661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DiazinonCCOP(=S)(OCC)OC1=NC(=NC(C)=C1)C(C)C2332.4Standard polar33892256
DiazinonCCOP(=S)(OCC)OC1=NC(=NC(C)=C1)C(C)C1789.8Standard non polar33892256
DiazinonCCOP(=S)(OCC)OC1=NC(=NC(C)=C1)C(C)C1781.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Diazinon EI-B (Non-derivatized)splash10-0ufr-3931000000-a70584cb463b920938492017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Diazinon EI-B (Non-derivatized)splash10-0ufr-3931000000-a70584cb463b920938492018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Diazinon GC-MS (Non-derivatized) - 70eV, Positivesplash10-03g1-2390000000-64dc2c6900828222f0d02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Diazinon GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0fbi-7920000000-dce70eb9e413a5f2e1a22014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Diazinon LC-ESI-QTOF , positive-QTOFsplash10-0a4i-0009000000-d239df985b8529964c592017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diazinon LC-ESI-QTOF , positive-QTOFsplash10-0ldi-0915000000-ced91e8448a6f8b1969d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diazinon LC-ESI-QTOF , positive-QTOFsplash10-0gb9-0900000000-48faf44580abfbba15e22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diazinon LC-ESI-QTOF , positive-QTOFsplash10-0gb9-0900000000-109fa8436bb829f5f4812017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diazinon LC-ESI-QTOF , positive-QTOFsplash10-0gb9-0900000000-49a403503b8e1237dddc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diazinon LC-ESI-ITFT , positive-QTOFsplash10-0gb9-0900000000-373a091bd4e337f273ac2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diazinon LC-ESI-ITFT , positive-QTOFsplash10-0a4i-0009000000-25cf20e874bc51155b112017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diazinon LC-ESI-ITFT , positive-QTOFsplash10-0pvi-0905000000-89807ca393822677be3e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diazinon LC-ESI-ITFT , positive-QTOFsplash10-0gb9-0900000000-95716b221cd9e83e7d052017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diazinon LC-ESI-ITFT , positive-QTOFsplash10-0gb9-1900000000-3772ba2a27f51803e58a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diazinon LC-ESI-ITFT , positive-QTOFsplash10-0uxs-4900000000-ce1c6d19b36209036e3a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diazinon LC-ESI-ITFT , positive-QTOFsplash10-0w2a-6900000000-8011c485731c42bd49f72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diazinon LC-ESI-ITFT , positive-QTOFsplash10-0a4i-0009000000-e92acd83cf908233bd112017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diazinon LC-ESI-ITFT , positive-QTOFsplash10-0aor-0905000000-54dc7dc28ca7ec93789e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diazinon LC-ESI-ITFT , positive-QTOFsplash10-0gb9-0900000000-cf4033176e3d7c36c5892017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diazinon LC-ESI-ITFT , positive-QTOFsplash10-0gb9-1900000000-cb95f2a89d6871b4c0f52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diazinon LC-ESI-ITFT , positive-QTOFsplash10-0uxs-3900000000-8d43918e6bdf5a7918272017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diazinon LC-ESI-ITFT , positive-QTOFsplash10-0w2a-7900000000-37289512a80be0d06b702017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diazinon LC-ESI-ITFT , positive-QTOFsplash10-0gb9-0900000000-c242d24704a15f911a562017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diazinon 10V, Positive-QTOFsplash10-0a4i-2398000000-292315df845ad237142a2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diazinon 20V, Positive-QTOFsplash10-002k-2490000000-b8c16809eaddcd92f2fb2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diazinon 40V, Positive-QTOFsplash10-00ko-9410000000-169637cf10237dcb2a0f2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diazinon 10V, Negative-QTOFsplash10-0ufr-0694000000-cdcbf19ad7bf249fbdb62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diazinon 20V, Negative-QTOFsplash10-00fs-0890000000-0b16a5fb1c0467d0de872016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diazinon 40V, Negative-QTOFsplash10-000b-0980000000-0e6aa8e81cb45755aac92016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB010928
KNApSAcK IDNot Available
Chemspider ID2909
KEGG Compound IDC14324
BioCyc IDCPD-8965
BiGG IDNot Available
Wikipedia LinkDiazinon
METLIN IDNot Available
PubChem Compound3017
PDB IDNot Available
ChEBI ID34682
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Rush T, Liu XQ, Hjelmhaug J, Lobner D: Mechanisms of chlorpyrifos and diazinon induced neurotoxicity in cortical culture. Neuroscience. 2010 Mar 31;166(3):899-906. doi: 10.1016/j.neuroscience.2010.01.025. Epub 2010 Jan 20. [PubMed:20096330 ]
  2. Coleman WE, Tardiff RG: Contaminant levels in animal feeds used for toxicity studies. Arch Environ Contam Toxicol. 1979;8(6):693-702. [PubMed:119496 ]
  3. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .