Prochloraz (CHEM002864)

Record Information
Version1.0
Creation Date2013-04-25 07:56:53 UTC
Update Date2026-08-19 10:14:49 UTC
Accession NumberCHEM002864
Identification
Common NameProchloraz
ClassSmall Molecule
Description
Prochloraz is an imidazole fungicide that is widely used in Europe, Australia, Asia and South America for gardening and agriculture. It can be used alone or in combination with other agents in case of fungal infestation of cereals. It is frequently used in the seed dressing to prevent fungal diseases of many crops, including oilseed rape, sugar beet, vegetables, rice and coffee, as well as for the protection of citrus fruits during storage and transport. Screening studies have shown that prochloraz elicits multiple mechanisms of action in vitro, as it antagonizes the androgen and the oestrogen receptor, agonizes the Ah receptor and inhibits aromatase activity. In vivo prochloraz acts as an antiandrogen
Contaminant Sources
  • HPV EPA Chemicals
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Amine
  • Ether
  • Fungicide
  • Organic Compound
  • Organochloride
  • Pesticide
  • Synthetic Compound
Chemical Structure
MOLSDF3D SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
N-Propyl-N-(2-(2,4,6-trichlorophenoxy)ethyl)-1H-imidazoleHMDB
Prochloraz-MNHMDB
Chemical FormulaC15H16Cl3N3O2
Average Molecular Mass376.665 g/mol
Monoisotopic Mass375.031 g/mol
CAS Registry Number67747-09-5
IUPAC NameN-propyl-N-[2-(2,4,6-trichlorophenoxy)ethyl]-1H-imidazole-1-carboxamide
Traditional Nameprochloraz
SMILESCCCN(CCOC1=C(Cl)C=C(Cl)C=C1Cl)C(=O)N1C=CN=C1
InChI IdentifierInChI=1S/C15H16Cl3N3O2/c1-2-4-20(15(22)21-5-3-19-10-21)6-7-23-14-12(17)8-11(16)9-13(14)18/h3,5,8-10H,2,4,6-7H2,1H3
InChI KeyTVLSRXXIMLFWEO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol ethers
Sub ClassNot Available
Direct ParentPhenol ethers
Alternative Parents
Substituents
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Imidazole-1-carbonyl group
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • N-substituted imidazole
  • Azole
  • Heteroaromatic compound
  • Imidazole
  • Carbonic acid derivative
  • Urea
  • Organoheterocyclic compound
  • Azacycle
  • Ether
  • Organochloride
  • Organohalogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • 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 crystal solid.
Experimental Properties
PropertyValue
Melting Point46.5-49.3°C
Boiling PointNot Available
Solubility34 mg/l in water , >600g/l in acetone, xylene, ethanol, dichloromethane, toluene, ethylacetate.
Predicted Properties
PropertyValueSource
Water Solubility0.0091 g/LALOGPS
logP3.78ALOGPS
logP3.62ChemAxon
logS-4.6ALOGPS
pKa (Strongest Basic)2.75ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area47.36 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity90.99 m³·mol⁻¹ChemAxon
Polarizability35.73 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureOral (3)
Mechanism of ToxicityProchloraz acts in vitro as a an aromatase inhibitor, aryl hydrocarbon receptor agonist, androgen receptor antagonist, and estrogen receptor antagonist. (1)
MetabolismNot Available
Toxicity ValuesLD50: 1204 mg/kg (oral; rat) (2); LD50: >2000 mg/kg (dermal, rat) (2); LD50: >2.41 mg/l (inhalation, rat) (2)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesProchloraz is a non-systemic imidazole fungicide, an ergosterol biosynthesis inhibitor with contact and translaminar, protectant and eradicant activity. It is used in agriculture and horticulture against various plant diseases, especially Ascomycetes and Fungi Imperfecti. It is used to control foliar diseases of cereals (Pseudocercosporella, Pyrenophora, Rhynchosporium and Septoria spp.), field crops (such as Alternaria, Botrytis, Pyrenopeziza and Sclerotinia in oilseed rape, Ascochyta and Botrytis in legumes, Pyricularia in rice), fruit (blossom blight) and vegetables (anthracnose). (2)
Minimum Risk LevelNot Available
Health EffectsSuspected endocrine disruptor (1).
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0062513
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 IDNot Available
ChEBI ID8434
PubChem Compound ID73665
Kegg Compound IDC11182
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=24401010
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24964350
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=25163568