Basic Info

Common NameProximphan(F04026)
2D Structure
Description

Proximphan 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 IDF04026
CAS Number2828-42-4
PubChem CID17808
FormulaC10H12N2O2
IUPAC Name

(propan-2-ylideneamino) N-phenylcarbamate

InChI Key

LATYTXGNKNKTDS-UHFFFAOYSA-N

InChI

InChI=1S/C10H12N2O2/c1-8(2)12-14-10(13)11-9-6-4-3-5-7-9/h3-7H,1-2H3,(H,11,13)

Canonical SMILES

CC(=NOC(=O)NC1=CC=CC=C1)C

Isomeric SMILES

CC(=NOC(=O)NC1=CC=CC=C1)C

Synonyms
        
            O-(N-Phenylcarbamoyl)propanonoxime
        
            Proxypham
        
            PROXIMPHAM
        
            Proximphan
        
            Acetone O-carbaniloyloxime
        
            Acetone oxime phenylurethane
        
            Proximpham [German]
        
            O-(N-Phenylcarbamoyl) 2-propanone oxime
        
            Acetone, O-(phenylcarbamoyl)oxime
        
            O-(N-Phenylcarbamoyl)-propanonoxim
        
Classifies
                

                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic nitrogen compounds
ClassOrganonitrogen compounds
SubclassOxime carbamates
Intermediate Tree NodesNot available
Direct ParentOxime carbamates
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsOxime carbamate - Benzenoid - Monocyclic benzene moiety - Ketoxime - Carbonic acid derivative - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as oxime carbamates. These are oxime ether derivatives with the general formula CC(R)=NOC(=O)N(R')R\", where R-R\" = H or organyl.

Properties

Property NameProperty Value
Molecular Weight192.218
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count3
Complexity216
Monoisotopic Mass192.09
Exact Mass192.09
XLogP1.7
Formal Charge0
Heavy Atom Count14
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+0.9533
Human Intestinal AbsorptionHIA+1.0000
Caco-2 PermeabilityCaco2+0.6013
P-glycoprotein SubstrateNon-substrate0.7761
P-glycoprotein InhibitorNon-inhibitor0.9056
Non-inhibitor0.9003
Renal Organic Cation TransporterNon-inhibitor0.9295
Distribution
Subcellular localizationMitochondria0.7420
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7799
CYP450 2D6 SubstrateNon-substrate0.8340
CYP450 3A4 SubstrateNon-substrate0.5724
CYP450 1A2 InhibitorInhibitor0.6845
CYP450 2C9 InhibitorNon-inhibitor0.7696
CYP450 2D6 InhibitorNon-inhibitor0.9099
CYP450 2C19 InhibitorNon-inhibitor0.7386
CYP450 3A4 InhibitorNon-inhibitor0.9684
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.7695
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9741
Non-inhibitor0.9751
AMES ToxicityAMES toxic0.5758
CarcinogensCarcinogens 0.5787
Fish ToxicityHigh FHMT0.9344
Tetrahymena Pyriformis ToxicityHigh TPT0.9581
Honey Bee ToxicityHigh HBT0.5276
BiodegradationNot ready biodegradable0.9934
Acute Oral ToxicityIII0.8015
Carcinogenicity (Three-class)Non-required0.6061

Model Value Unit
Absorption
Aqueous solubility-2.4057LogS
Caco-2 Permeability1.6466LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.1271LD50, mol/kg
Fish Toxicity0.6255pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.4393pIGC50, 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