ContaminantDB: Difenoconazole

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (30)XML

Record Information

Version

1.0

Creation Date

2013-04-25 07:56:51 UTC

Update Date

2016-11-09 01:08:58 UTC

Accession Number

CHEM002789

Identification

Common Name

Difenoconazole

Class

Small Molecule

Description

Difenoconazole is a broad spectrum fungicide that controls a wide variety of fungi – including members of the Aschomycetes, Basidomycetes and Deuteromycetes families. It acts as a seed treatment, foliar spray and systemic fungicide. It is taken up through the surface of the infected plant and is translocated to all parts of the plant. It has a curative effect and a preventative effect. Difenoconazole can be applied to winter wheat, oilseed rape, Brussels sprouts, cabbage, broccoli/calabrese and cauliflower. It controls various fungi including Septoria tritici, Brown Rust, Light Leaf Spot, Leaf Spot, Pod Spot, Ring Spot and Stem canker. It also prevents Ear Discolouration in winter wheat. The mode of action of difenoconazole is that it is a sterol demethylation inhibitor which prevents the development of the fungus by inhibiting cell membrane ergosterol biosynthesis.

Contaminant Sources

My Exposome Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Ether
Fungicide
Organic Compound
Organochloride
Pesticide
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Difenoconazol	ChEMBL

Chemical Formula

C₁₉H₁₇Cl₂N₃O₃

Average Molecular Mass

406.263 g/mol

Monoisotopic Mass

405.065 g/mol

CAS Registry Number

119446-68-3

IUPAC Name

1-({2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole

Traditional Name

difenoconazole

SMILES

CC1COC(CN2C=NC=N2)(O1)C1=C(Cl)C=C(OC2=CC=C(Cl)C=C2)C=C1

InChI Identifier

InChI=1S/C19H17Cl2N3O3/c1-13-9-25-19(27-13,10-24-12-22-11-23-24)17-7-6-16(8-18(17)21)26-15-4-2-14(20)3-5-15/h2-8,11-13H,9-10H2,1H3

InChI Key

BQYJATMQXGBDHF-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylethers

Direct Parent

Diphenylethers

Alternative Parents

Substituents

Diphenylether
Diaryl ether
Phenoxy compound
Phenol ether
Chlorobenzene
Ketal
Halobenzene
Aryl chloride
Aryl halide
Meta-dioxolane
Azole
Heteroaromatic compound
1,2,4-triazole
Ether
Acetal
Oxacycle
Organoheterocyclic compound
Azacycle
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

aromatic ether (CHEBI:81760 )
dioxolane (CHEBI:81760 )
triazoles (CHEBI:81760 )
cyclic ketal (CHEBI:81760 )
triazole fungicide (CHEBI:81760 )
conazole fungicide (CHEBI:81760 )
Conazole fungicides (C18459 )

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 powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0041 g/L	ALOGPS
logP	4.18	ALOGPS
logP	4.86	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Basic)	2.24	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	58.4 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	113.98 m³·mol⁻¹	ChemAxon
Polarizability	38.82 Å³	ChemAxon
Number of Rings	4	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	splash10-0a4l-9023000000-ea5704f754eaf5299869	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0f79-0079000000-9b88cf6e5909b7d45d16	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-0a4i-0000900000-3053e4a0a979a7206562	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-0udi-0090000000-15f5ca653f00ea45daa0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0udi-0091000000-cb0c97ae96929a2f5432	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-0a4i-0000900000-608c632db7a9468fb3b1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-0udi-0290000000-bfb90bf5e3c018fad963	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-0udi-0090000000-2eacea58497fadedeca1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-0a4i-0001900000-9806cc5ead365c8ee36e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0udi-0092100000-da0496ed4c42f62ddeb4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-0udi-0090000000-cb298e1a46e0a954d0ff	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0udi-0390000000-6705241c665e660047d3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-0930800000-a479da71a4305469d74a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0zfr-0190500000-26f33ca71fbfb4388fff	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0pb9-0084900000-7af9c135021ca0aef9b9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-0090000000-4e2a9250675736a9148e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-0udi-0390000000-ab5d44996dc8b7713104	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0f79-0079000000-650c1df9ed18fc4ba036	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0udi-0390000000-793c4f193127b50d447f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-0f79-0920000000-8f8f58d0101fbd13449d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-1002900000-63087c2634dd749c241c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-2009000000-a5b1d8476e7567ac024b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9261000000-eb82d422393084a62cdd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-9000200000-47f376d04a96c3b4eb26	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-9000000000-6e58735ce2565cc3f043	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014l-9101000000-53d5f4f334db713fbb6e	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-01b9-4696000000-db326a3d603f54518d5c	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

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

Uses/Sources

This is a man-made compound that is used as a pesticide.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0251255

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

77730

ChEBI ID

81760

PubChem Compound ID

Not Available

Kegg Compound ID

C18459

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=24405376

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=25172726

3. https://www.ncbi.nlm.nih.gov/pubmed/?term=25306325

Difenoconazole (CHEM002789)

Structure for CHEM002789: Difenoconazole