Myclobutanil (CHEM002850)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (19)XML
Record Information
Version1.0
Creation Date2013-04-25 07:56:53 UTC
Update Date2016-11-09 01:08:59 UTC
Accession NumberCHEM002850
Identification
Common NameMyclobutanil
ClassSmall Molecule
DescriptionMyclobutanil is a triazole chemical used as a fungicide. It is a steroid demethylation inhibitor, specifically inhibiting ergosterol biosynthesis. Ergosterol is a critical component of fungal cell membranes.
Contaminant Sources
  • Clean Air Act Chemicals
  • EPA Endocrine Screening
  • HPV EPA Chemicals
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amine
  • Fungicide
  • Household Toxin
  • Nitrile
  • Organic Compound
  • Organochloride
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
SysthaneHMDB
(R)-2-p-Chlorophenyl-2-(1H-1,2,4-triazol-1-ylmethyl)hexanenitrileHMDB
Chemical FormulaC15H17ClN4
Average Molecular Mass288.775 g/mol
Monoisotopic Mass288.114 g/mol
CAS Registry Number88671-89-0
IUPAC Name2-(4-chlorophenyl)-2-[(1H-1,2,4-triazol-1-yl)methyl]hexanenitrile
Traditional Namemyclobutanil
SMILESCCCCC(CN1C=NC=N1)(C#N)C1=CC=C(Cl)C=C1
InChI IdentifierInChI=1S/C15H17ClN4/c1-2-3-8-15(9-17,10-20-12-18-11-19-20)13-4-6-14(16)7-5-13/h4-7,11-12H,2-3,8,10H2,1H3
InChI KeyHZJKXKUJVSEEFU-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as chlorobenzenes. Chlorobenzenes are compounds containing one or more chlorine atoms attached to a benzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassHalobenzenes
Direct ParentChlorobenzenes
Alternative Parents
Substituents
  • Chlorobenzene
  • Aryl chloride
  • Aryl halide
  • Azole
  • Heteroaromatic compound
  • 1,2,4-triazole
  • Azacycle
  • Carbonitrile
  • Nitrile
  • Organoheterocyclic compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organohalogen compound
  • Organochloride
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical Roles
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point63°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.086 g/LALOGPS
logP2.8ALOGPS
logP3.66ChemAxon
logS-3.5ALOGPS
pKa (Strongest Basic)2.27ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area54.5 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity91.68 m³·mol⁻¹ChemAxon
Polarizability30.18 ųChemAxon
Number of Rings2ChemAxon
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, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 20V, positivesplash10-00di-0490000000-fcfb99794b82c3ede1a6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 8V, positivesplash10-000i-0090000000-100c47c9c42d51443cfbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 17V, positivesplash10-0079-6190000000-3b99b485c30ee59460dfSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 25V, positivesplash10-00fr-9800000000-4558553a7d268304c28eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 34V, positivesplash10-00b9-5900000000-e18bee0f7cdf70389c3eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 43V, positivesplash10-00b9-4900000000-3c9e94084d58ea9a05b0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 51V, positivesplash10-00b9-4900000000-68d11140a84852a61471Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 20V, positivesplash10-00dr-9260000000-c20f8d7cf640d18c5ca7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, positivesplash10-000i-0090000000-1023ba33e7f36a8678dbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, positivesplash10-002r-0690000000-af12a61338305b399066Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 30V, positivesplash10-004i-0900000000-0b762c59ca809e949601Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 40V, positivesplash10-004i-0900000000-7289f613731c193ad668Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 50V, positivesplash10-004i-0900000000-dc5019d4c2b90807de9bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 26V, positivesplash10-00di-9410000000-9641ac1cca4c00b9bbd1Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0079-6190000000-3b99b485c30ee59460dfSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-00di-0490000000-504bec76aff3e03667ecSpectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-00di-0490000000-a9180023808b2400ce61Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-00fr-9800000000-4558553a7d268304c28eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 25V, Positivesplash10-000i-0090000000-f73f96055bd40b47f77cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-0090000000-a095f596c21a6b4dbde1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dj-0090000000-d266056e3662d044ac02Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9340000000-7fbabd9caa575c48d1afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014r-9080000000-bccc3e6f3f1711478e8eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-9080000000-72f9d4ede1b66ba410aaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-7ae9fb504c0935db938eSpectrum
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)
MetabolismMyclobutanil metabolizes into 1,2,4-triazole, which has a lower acute toxicity than the parent compound (3). Organic 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 ValuesLD50: 1.75 to 1.8 g/kg (rats, oral) (3)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesMyclobutanil is a man-made compound that is used as a pesticide. Myclobutanil is registered for use on a wide range of food and feed crops. It may also be used in greenhouses, public rights of way, turf, and in landscaping applications. Cotton seeds may be treated with myclobutanil. California accounts for roughly 50% of all myclobutanil use in the US, using 70,000 to 90,000 lbs. annually. Grapes are the most heavily treated crop, using 60% of all myclobutanil in California. Almonds and strawberries are also account for a notable percentage of myclobutanil use in California. (3)
Minimum Risk LevelNot Available
Health EffectsMyclobutanil is listed as a developmental toxin (4).
SymptomsWorkers exposed to myclobutanil have reported symptoms such as skin rash, allergic dermatitis, itchiness, nausea, heachache, diarrhea, abdominal pain, vomiting, nosebleed, and eye irritation (3).
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0243541
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMyclobutanil
Chemspider ID6096
ChEBI ID83729
PubChem Compound ID6336
Kegg Compound IDC18477
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26.