Basic Info

Common NameFormetanate(F03997)
2D Structure
Description

Formetanate 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 IDF03997
CAS Number22259-30-9
PubChem CID31099
FormulaC11H15N3O2
IUPAC Name

[3-(dimethylaminomethylideneamino)phenyl] N-methylcarbamate

InChI Key

RMFNNCGOSPBBAD-UHFFFAOYSA-N

InChI

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

Canonical SMILES

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

Isomeric SMILES

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

Synonyms
        
            Formetanate [ANSI:BSI:ISO]
        
            FORMETANATE
        
            Dicarzol
        
            Formetanat
        
            22259-30-9
        
            Caswell No. 465A
        
            UNII-532HEC1KKM
        
            EINECS 244-879-0
        
            EP 322
        
            EPA Pesticide Chemical Code 465200
        
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 - Carbonyl group - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - 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 Weight221.26
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count4
Complexity254
Monoisotopic Mass221.116
Exact Mass221.116
XLogP1.2
Formal Charge0
Heavy Atom Count16
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9316
Human Intestinal AbsorptionHIA+0.9714
Caco-2 PermeabilityCaco2+0.5688
P-glycoprotein SubstrateNon-substrate0.7791
P-glycoprotein InhibitorNon-inhibitor0.8777
Non-inhibitor0.8074
Renal Organic Cation TransporterNon-inhibitor0.8396
Distribution
Subcellular localizationMitochondria0.6860
Metabolism
CYP450 2C9 SubstrateNon-substrate0.6546
CYP450 2D6 SubstrateNon-substrate0.6433
CYP450 3A4 SubstrateSubstrate0.5884
CYP450 1A2 InhibitorInhibitor0.5420
CYP450 2C9 InhibitorNon-inhibitor0.8844
CYP450 2D6 InhibitorNon-inhibitor0.9107
CYP450 2C19 InhibitorNon-inhibitor0.8119
CYP450 3A4 InhibitorNon-inhibitor0.8836
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.7963
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.8971
Non-inhibitor0.8736
AMES ToxicityAMES toxic0.6229
CarcinogensNon-carcinogens0.5689
Fish ToxicityHigh FHMT0.8682
Tetrahymena Pyriformis ToxicityHigh TPT0.8937
Honey Bee ToxicityHigh HBT0.5308
BiodegradationNot ready biodegradable0.9773
Acute Oral ToxicityI0.7818
Carcinogenicity (Three-class)Non-required0.5856

Model Value Unit
Absorption
Aqueous solubility-2.4023LogS
Caco-2 Permeability1.1686LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity4.0127LD50, mol/kg
Fish Toxicity0.7628pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.4493pIGC50, ug/L

References

TitleJournalDatePubmed ID
Formetanate toxicity and changes in antioxidant enzyme system of Apis melliferalarvae.Environ Sci Pollut Res Int2017 Jun28409431
Laccase-Prussian blue film-graphene doped carbon paste modified electrode forcarbamate pesticides quantification.Biosens Bioelectron2013 Sep 1523587791
Determination of pesticides in soy-based infant formula using liquidchromatography with electrospray ionization tandem mass spectrometry.J AOAC Int2006 Jan-Feb16512251
Determination of pesticides in apple-based infant foods using liquidchromatography electrospray ionization tandem mass spectrometry.J Agric Food Chem2005 Feb 915686398
An index for selective toxicity of miticides to phytophagous mites and their predators based on orchard trials.Pest Manag Sci2003 Dec14667054
Insecticide resistance in field populations of Frankliniella occidentalis(Pergande) in Murcia (south-east Spain).Pest Manag Sci2002 Sep12233190

Targets

General Function:
Serine hydrolase activity
Specific Function:
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name:
ACHE
Uniprot ID:
P22303
Molecular Weight:
67795.525 Da
References
  1. Fishel F (2009). Pesticide Toxicity Profile: Carbamate Pesticides. University of Florida, IFAS Extension.: http://edis.ifas.ufl.edu/PI088
General Function:
Identical protein binding
Specific Function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular Weight:
68417.575 Da
Mechanism of Action:
Like the organophosphates, their mode of action is inhibition of cholinesterase enzymes, affecting nerve impulse transmission.
References
  1. Fishel F (2009). Pesticide Toxicity Profile: Carbamate Pesticides. University of Florida, IFAS Extension.: http://edis.ifas.ufl.edu/PI088