Boscalid (CHEM002761)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (12)XML
Record Information
Version1.0
Creation Date2013-04-25 07:56:50 UTC
Update Date2016-11-09 01:08:58 UTC
Accession NumberCHEM002761
Identification
Common NameBoscalid
ClassSmall Molecule
DescriptionBoscalid is a fungicide developed by BASF and launched in 2003 for use on food crops. It works as a succinate dehydrogenase inhibitor to kill fungal target organisms. It is practically nontoxic to terrestrial animals and is moderately toxic to aquatic animals on an acute exposure basis. In subchronic and chronic feeding studies in rats, mice and dogs, boscalid generally caused decreased body weights and body weight gains (primarily in mice) and effects on the liver (increase in weights, changes in enzyme levels and histopathological changes) as well as on the thyroid (increase in weights and histopathological changes). In a developmental toxicity study in rats, no developmental toxicity was observed in the fetuses at the highest dose tested. Boscalid is classified as, suggestive evidence of carcinogenicity, but not sufficient to assess human carcinogenic potential, according to the EPA.
Contaminant Sources
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Amine
  • Ester
  • Food Toxin
  • Fungicide
  • Organic Compound
  • Organochloride
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Chloro-N-(4'-chloro[1,1'-biphenyl]-2-yl)-3-pyridinecarboxamideChEBI
2-Chloro-N-(4'-chloro[1,1'-biphenyl]-2-yl)pyridine-3-carboxamideChEBI
2-chloro-N-(4-Chlorobiphenyl-2-yl)nicotinamideMeSH
Chemical FormulaC18H12Cl2N2O
Average Molecular Mass343.207 g/mol
Monoisotopic Mass342.033 g/mol
CAS Registry Number188425-85-6
IUPAC Name2-chloro-N-{4'-chloro-[1,1'-biphenyl]-2-yl}pyridine-3-carboxamide
Traditional Nameboscalid
SMILESClC1=CC=C(C=C1)C1=C(NC(=O)C2=C(Cl)N=CC=C2)C=CC=C1
InChI IdentifierInChI=1S/C18H12Cl2N2O/c19-13-9-7-12(8-10-13)14-4-1-2-6-16(14)22-18(23)15-5-3-11-21-17(15)20/h1-11H,(H,22,23)
InChI KeyWYEMLYFITZORAB-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as aromatic anilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with an aromatic group. They have the general structure RNC(=O)R', where R= benzene, and R = aryl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAnilides
Direct ParentAromatic anilides
Alternative Parents
Substituents
  • Aromatic anilide
  • Chlorinated biphenyl
  • Biphenyl
  • Nicotinamide
  • Pyridinecarboxamide
  • Pyridine carboxylic acid or derivatives
  • Chlorobenzene
  • Halobenzene
  • 2-halopyridine
  • Pyridine
  • Aryl halide
  • Aryl chloride
  • Vinylogous halide
  • Heteroaromatic compound
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organohalogen compound
  • Organic oxygen compound
  • Organochloride
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organic oxide
  • 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
ApplicationsNot Available
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 Solubility0.00075 g/LALOGPS
logP4.91ALOGPS
logP4.92ChemAxon
logS-5.7ALOGPS
pKa (Strongest Acidic)12.06ChemAxon
pKa (Strongest Basic)-0.11ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area41.99 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity95.24 m³·mol⁻¹ChemAxon
Polarizability33.9 ųChemAxon
Number of Rings3ChemAxon
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 , negativesplash10-0006-0009000000-08bb054d30b013df8c3aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0006-0009000000-fd23b8bb2b3eca18d170Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-0900000000-576980b20b4f9254c0a7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-0920000000-018f832c24ec5e51d031Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-01t9-0790000000-b60e0536295f0f6f282bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0009000000-1e0db928185a7c40e0acSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0006-0009000000-85c9fae68389f66ef539Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4l-0109000000-35390100c1c858f08950Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0249000000-255b3e9ea0c165968aa2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0292000000-9a2a555807653da18eddSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-1290000000-245c46bd849f5f30c9dfSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00dl-1290000000-55dae94ea9ffe2501875Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0006-0009000000-85dda4095cd906af3a3aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4l-0109000000-6b7ac2e9e77726c22d55Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0249000000-e9a7fa91517adaaa6474Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0292000000-621dc4c81d2c4fddc0b0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-1290000000-5a5348758876aeb7aa0dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00dl-1290000000-68a8a92797d7e0bcc8baSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0009000000-6329d742a309c6964c06Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0029000000-394375ad83fc8d7d2b46Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f6x-0269000000-5cf34c5315292816ef3aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-5982000000-8575b981f752a80b50a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-a75649df0c3b066935abSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0329000000-3421bbf7bf3471368e9dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0r29-4594000000-4b65f05a7caf251f35bcSpectrum
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 IDDB12792
HMDB IDHMDB0249353
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID184713
ChEBI ID81822
PubChem Compound IDNot Available
Kegg Compound IDC18547
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=24380616
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24711278
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=24893153
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=24901961
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=24936710