ContaminantDB: Prochloraz

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (36)XML

Record Information

Version

1.0

Creation Date

2013-04-25 07:56:53 UTC

Update Date

2026-03-31 19:49:44 UTC

Accession Number

CHEM002864

Identification

Common Name

Prochloraz

Class

Small 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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
N-Propyl-N-(2-(2,4,6-trichlorophenoxy)ethyl)-1H-imidazole	HMDB
Prochloraz-MN	HMDB

Chemical Formula

C₁₅H₁₆Cl₃N₃O₂

Average Molecular Mass

376.665 g/mol

Monoisotopic Mass

375.031 g/mol

CAS Registry Number

67747-09-5

IUPAC Name

N-propyl-N-[2-(2,4,6-trichlorophenoxy)ethyl]-1H-imidazole-1-carboxamide

Traditional Name

prochloraz

SMILES

CCCN(CCOC1=C(Cl)C=C(Cl)C=C1Cl)C(=O)N1C=CN=C1

InChI Identifier

InChI=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 Key

TVLSRXXIMLFWEO-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenol ethers

Sub Class

Not Available

Direct Parent

Phenol 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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

aromatic ether (CHEBI:8434 )
ureas (CHEBI:8434 )
imidazoles (CHEBI:8434 )
trichlorobenzene (CHEBI:8434 )
amide fungicide (CHEBI:8434 )
imidazole fungicide (CHEBI:8434 )
conazole fungicide (CHEBI:8434 )
Amide fungicides (C11182 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White crystal solid.

Experimental Properties

Property	Value
Melting Point	46.5-49.3°C
Boiling Point	Not Available
Solubility	34 mg/l in water , >600g/l in acetone, xylene, ethanol, dichloromethane, toluene, ethylacetate.

Predicted Properties

Property	Value	Source
Water Solubility	0.0091 g/L	ALOGPS
logP	3.78	ALOGPS
logP	3.62	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Basic)	2.75	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	47.36 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	90.99 m³·mol⁻¹	ChemAxon
Polarizability	35.73 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00mn-9600000000-e3f1ea44e71dcb51a115	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0a4i-0009000000-0ae79f14e960df4bd6a1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0a4i-0019000000-a4cad4c2d27e0a00f713	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0ab9-4049000000-c2057b244ebdd5ab5657	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-00di-9120000000-0c81235ba823fac1cfab	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-00di-9210000000-597ced463ae1e858953e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-00di-9610000000-df1ee809ffe2b4459f6e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-00xr-6910000000-57a6bf28f0ea23b864a3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0a4i-0019000000-91b319fb1a6e7777ede5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0a4i-4069000000-225b6a986f3dc3d0587e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-00di-9120000000-46b8460a97c9653aee9a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-00di-9410000000-c93a2e4fd9bcd6127fef	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-00di-9600000000-9fcaab5a55a00be40df3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-00xr-4900000000-57c2c3ba2bd53bbb5dd5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0a4i-0009000000-5ba733f6eda35e12362a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-053r-0298000000-43f074e6f36a1234e94a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-053r-0296000000-8970d3b3dccb40b5cd40	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0ab9-6129000000-04a16f54678b2eb848a5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0a4i-0029000000-c07acfd90f90af9bc2bf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-05fr-9075000000-13b15aa68191fddb1897	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00or-5209000000-b212e72b864d55b5d685	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-9402000000-0a6b387ecded9dac65fd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014l-9100000000-b04c3c6d40f7449aa7a6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-1409000000-c02564cc693574d2f6f5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-1906000000-dc8e3ee3cdad740a721b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0296-7931000000-51212958609e711c56aa	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-006x-9313000000-56ec4bdef0bfb8b84a37	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral (3)

Mechanism of Toxicity

Prochloraz acts in vitro as a an aromatase inhibitor, aryl hydrocarbon receptor agonist, androgen receptor antagonist, and estrogen receptor antagonist. (1)

Metabolism

Not Available

Toxicity Values

LD50: 1204 mg/kg (oral; rat) (2); LD50: >2000 mg/kg (dermal, rat) (2); LD50: >2.41 mg/l (inhalation, rat) (2)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Prochloraz 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 Level

Not Available

Health Effects

Suspected endocrine disruptor (1).

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0062513

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

Not Available

ChEBI ID

8434

PubChem Compound ID

73665

Kegg Compound ID

C11182

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not 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

Prochloraz (CHEM002864)

Structure for CHEM002864: Prochloraz