Basic Info

Common NamePromecarb(F04021)
2D Structure
Description

Promecarb 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 IDF04021
CAS Number2631-37-0
PubChem CID17516
FormulaC12H17NO2
IUPAC Name

(3-methyl-5-propan-2-ylphenyl) N-methylcarbamate

InChI Key

DTAPQAJKAFRNJB-UHFFFAOYSA-N

InChI

InChI=1S/C12H17NO2/c1-8(2)10-5-9(3)6-11(7-10)15-12(14)13-4/h5-8H,1-4H3,(H,13,14)

Canonical SMILES

CC1=CC(=CC(=C1)OC(=O)NC)C(C)C

Isomeric SMILES

CC1=CC(=CC(=C1)OC(=O)NC)C(C)C

Synonyms
        
            m-Cym-5-yl methylcarbamate
        
            PROMECARB
        
            Carbamult
        
            Promecarbe
        
            Minacide
        
            2631-37-0
        
            Schering 34615
        
            Morton EP-316
        
            Sch 34615
        
            Nor-Am
        
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 - Cumene - Phenylpropane - Phenoxy compound - Toluene - Carbamic acid ester - Carbonic acid derivative - Carbonyl group - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organooxygen compound - Organonitrogen compound - Organic oxygen compound - Organic nitrogen 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 Weight207.273
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count3
Complexity216
Monoisotopic Mass207.126
Exact Mass207.126
XLogP3.1
Formal Charge0
Heavy Atom Count15
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+0.9464
Human Intestinal AbsorptionHIA+1.0000
Caco-2 PermeabilityCaco2+0.7505
P-glycoprotein SubstrateNon-substrate0.8432
P-glycoprotein InhibitorNon-inhibitor0.9435
Non-inhibitor0.9620
Renal Organic Cation TransporterNon-inhibitor0.9077
Distribution
Subcellular localizationMitochondria0.7591
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7637
CYP450 2D6 SubstrateSubstrate0.7942
CYP450 3A4 SubstrateSubstrate0.5937
CYP450 1A2 InhibitorNon-inhibitor0.5974
CYP450 2C9 InhibitorNon-inhibitor0.9618
CYP450 2D6 InhibitorNon-inhibitor0.9140
CYP450 2C19 InhibitorNon-inhibitor0.9180
CYP450 3A4 InhibitorNon-inhibitor0.9448
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8285
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9508
Non-inhibitor0.9609
AMES ToxicityAMES toxic0.5218
CarcinogensNon-carcinogens0.8225
Fish ToxicityHigh FHMT0.8583
Tetrahymena Pyriformis ToxicityHigh TPT0.9414
Honey Bee ToxicityHigh HBT0.8784
BiodegradationNot ready biodegradable0.7922
Acute Oral ToxicityI0.5604
Carcinogenicity (Three-class)Non-required0.5954

Model Value Unit
Absorption
Aqueous solubility-2.9104LogS
Caco-2 Permeability1.6741LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity3.1022LD50, mol/kg
Fish Toxicity1.2069pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.2340pIGC50, ug/L

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