ContaminantDB: Pyridaben

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (28)XML

Record Information

Version

1.0

Creation Date

2013-04-25 07:56:54 UTC

Update Date

2016-11-09 01:08:59 UTC

Accession Number

CHEM002876

Identification

Common Name

Pyridaben

Class

Small Molecule

Description

Pyridaben is an insecticide and acaricide that is effective against thrips, mites, aphids and leafhoppers. It can be used to treat insect infestations in citrus and other fruit orchards. It was discovered and introduced by Nissan Chemical Industries, Ltd and first marketed in Belgium in 1990. It has a low aqueous solubility, not considered particulatly volatile and, based on its chemical properties, is not expected to leach to groundwater. It is moderately toxic to mammals and not expected to bioaccumulate. It is highly toxic to most aquatic organisms and honey bees but less so to earthworms and birds. (1)

Contaminant Sources

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

Contaminant Type

Ester
Ether
Insecticide
Organic Compound
Organochloride
Pesticide
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4-Chloro-2-(1,1-dimethylethyl)-5-(((4-(1,1-dimethylethyl)phenyl)methyl)thio)-3(2H)-pyridazinone	ChEBI
Sanmite	ChEBI
2-Tert-butyl-5-(4-tert-butyl-benzylthio)-4-chloropyridazin-3(2H)-one	MeSH

Chemical Formula

C₁₉H₂₅ClN₂OS

Average Molecular Mass

364.933 g/mol

Monoisotopic Mass

364.138 g/mol

CAS Registry Number

96489-71-3

IUPAC Name

2-tert-butyl-5-{[(4-tert-butylphenyl)methyl]sulfanyl}-4-chloro-2,3-dihydropyridazin-3-one

Traditional Name

pyridaben

SMILES

CC(C)(C)N1N=CC(SCC2=CC=C(C=C2)C(C)(C)C)=C(Cl)C1=O

InChI Identifier

InChI=1S/C19H25ClN2OS/c1-18(2,3)14-9-7-13(8-10-14)12-24-15-11-21-22(19(4,5)6)17(23)16(15)20/h7-11H,12H2,1-6H3

InChI Key

DWFZBUWUXWZWKD-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylpropanes

Direct Parent

Phenylpropanes

Alternative Parents

Substituents

Phenylpropane
Aryl thioether
Pyridazinone
Alkylarylthioether
Aryl chloride
Aryl halide
Pyridazine
Vinylogous thioester
Heteroaromatic compound
Lactam
Azacycle
Thioether
Sulfenyl compound
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

organochlorine insecticide (CHEBI:38626 )
pyridazinone (CHEBI:38626 )
organochlorine acaricide (CHEBI:38626 )
Pesticides (C18614 )

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

mitochondrial NADH:ubiquinone reductase inhibitor

Chemical Roles

mitochondrial NADH:ubiquinone reductase inhibitor

Physical Properties

State

Solid

Appearance

White crystals.

Experimental Properties

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

Predicted Properties

Property	Value	Source
Water Solubility	0.00024 g/L	ALOGPS
logP	5.52	ALOGPS
logP	5.2	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	32.67 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	105.53 m³·mol⁻¹	ChemAxon
Polarizability	38.97 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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	Not Available	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-QTOF 10V, positive	splash10-0a4i-0009000000-5f4755977cad1dfdc13f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 20V, positive	splash10-0a4j-0309000000-8d10e240f475ede0d247	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 30V, positive	splash10-0002-0900000000-07cc27e240b9f7970542	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 50V, positive	splash10-000t-0900000000-9182df75efb26f2cdcdb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 28V, positive	splash10-0002-0903000000-9cb6e5154bb3bffc0c21	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-0159-0900000000-43432569f53b3de8ac9c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-015a-0900000000-1f92c2e392b74bdb3f73	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0002-0902000000-703f90b510ace30b4975	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-0a4i-0009000000-79889298db9601e5a042	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-0002-0900000000-fabc24c805bbb32e4b70	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-0002-0900000000-65e73bc48a8675df33b6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-000t-0900000000-9182df75efb26f2cdcdb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0002-0900000000-07cc27e240b9f7970542	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0009000000-5f4755977cad1dfdc13f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0a4j-0309000000-8d10e240f475ede0d247	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-066r-0009000000-3b8740ee98b8eeed32c0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056r-0619000000-beaa9edd8a24e66612fb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-0922000000-cfcf24cf44625840aafb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0009000000-f0c4bf7a4e461477c429	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03dr-2935000000-e9c1f257b398deb99bd1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-4900000000-fc406ae7d9987403d1cd	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0002-0901000000-6293bd206d65f770c980	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

LD50: 161 mg/kg (acute, rat) (1)

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 an insecticide effective against thrips, mites, aphids and leafhoppers.

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

HMDB0256960

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

82852

ChEBI ID

38626

PubChem Compound ID

Not Available

Kegg Compound ID

C18614

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Pyridaben (CHEM002876)

Structure for CHEM002876: Pyridaben