Basic Info

Common NameFormetanate Hydrochloride(F03998)
2D Structure
Description

Formetanate hydrochloride is a carbamate pesticide. Carbamate pesticides are derived from carbamic acid and kill insects in a similar fashion as organophosphate insecticides. They are widely used in homes, gardens and agriculture. The first carbamate, carbaryl, was introduced in 1956 and more of it has been used throughout the world than all other carbamates combined. Because of carbaryl's relatively low mammalian oral and dermal toxicity and broad control spectrum, it has had wide use in lawn and garden settings. Most of the carbamates are extremely toxic to Hymenoptera, and precautions must be taken to avoid exposure to foraging bees or parasitic wasps. Some of the carbamates are translocated within plants, making them an effective systemic treatment. (L795)

FRCD IDF03998
CAS Number23422-53-9
PubChem CID31899
FormulaC11H16ClN3O2
IUPAC Name

[3-(dimethylaminomethylideneamino)phenyl] N-methylcarbamate;hydrochloride

InChI Key

MYPKGPZHHQEODQ-UHFFFAOYSA-N

InChI

InChI=1S/C11H15N3O2.ClH/c1-12-11(15)16-10-6-4-5-9(7-10)13-8-14(2)3;/h4-8H,1-3H3,(H,12,15);1H

Canonical SMILES

CNC(=O)OC1=CC=CC(=C1)N=CN(C)C.Cl

Isomeric SMILES

CNC(=O)OC1=CC=CC(=C1)N=CN(C)C.Cl

Synonyms
        
            Caswell No. 465B
        
            FORMETANATE HYDROCHLORIDE
        
            Carzol
        
            23422-53-9
        
            Formetanate HCl
        
            Carzol SP
        
            Carzol 92SP
        
            Schering 36056
        
            Morton EP 332
        
            UNII-W0Y3OP0N2Z
        
Classifies
                

                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassPhenyl methylcarbamates
Intermediate Tree NodesNot available
Direct ParentPhenyl methylcarbamates
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsPhenyl methylcarbamate - Phenoxy compound - Carbamic acid ester - Carbonic acid derivative - Amidine - Carboxylic acid amidine - Formamidine - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Organic nitrogen compound - Carbonyl group - Organooxygen compound - Organonitrogen compound - Hydrochloride - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as phenyl methylcarbamates. These are aromatic compounds containing a methylcarbamic acid esterified with a phenyl group.

Properties

Property NameProperty Value
Molecular Weight257.718
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count3
Rotatable Bond Count4
Complexity254
Monoisotopic Mass257.093
Exact Mass257.093
Formal Charge0
Heavy Atom Count17
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count2

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.8780
Human Intestinal AbsorptionHIA+0.9859
Caco-2 PermeabilityCaco2+0.5331
P-glycoprotein SubstrateNon-substrate0.7611
P-glycoprotein InhibitorNon-inhibitor0.9157
Non-inhibitor0.7242
Renal Organic Cation TransporterNon-inhibitor0.8484
Distribution
Subcellular localizationMitochondria0.7040
Metabolism
CYP450 2C9 SubstrateNon-substrate0.6272
CYP450 2D6 SubstrateNon-substrate0.6989
CYP450 3A4 SubstrateSubstrate0.6248
CYP450 1A2 InhibitorInhibitor0.5761
CYP450 2C9 InhibitorNon-inhibitor0.8159
CYP450 2D6 InhibitorNon-inhibitor0.8901
CYP450 2C19 InhibitorNon-inhibitor0.6586
CYP450 3A4 InhibitorNon-inhibitor0.7273
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.6563
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9076
Non-inhibitor0.8010
AMES ToxicityAMES toxic0.5503
CarcinogensCarcinogens 0.5090
Fish ToxicityHigh FHMT0.9130
Tetrahymena Pyriformis ToxicityHigh TPT0.9587
Honey Bee ToxicityLow HBT0.5668
BiodegradationNot ready biodegradable0.9969
Acute Oral ToxicityI0.6377
Carcinogenicity (Three-class)Non-required0.5682

Model Value Unit
Absorption
Aqueous solubility-2.8372LogS
Caco-2 Permeability1.1193LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity3.5098LD50, mol/kg
Fish Toxicity0.6900pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.5916pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Other SpicesJapan4ppm
Japanese Plum(Including Prune)Japan0.5ppm
NectarineJapan4ppm
PeachJapan4ppm
PearJapan3ppm
Japanese PearJapan3ppm
AppleJapan3ppm
Other Citrus FruitsJapan4ppm
LimeJapan4ppm
GrapefruitJapan4ppm
Orange(Including Navel Orange)Japan4ppm
LemonJapan4ppm
Unshu Orange,PulpJapan4ppm
ApplesCanada3mg/kg
Citrus FruitsCanada4mg/kg
Peaches/NectarinesCanada3mg/kg
PearsCanada3mg/kg
PlumsCanada0. 5mg/kg

References

TitleJournalDatePubmed ID
An index for selective toxicity of miticides to phytophagous mites and their predators based on orchard trials.Pest Manag Sci2003 Dec14667054