Basic Info

Common NamePropham(F04024)
2D Structure
Description

Propham 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 IDF04024
CAS Number122-42-9
PubChem CID24685
FormulaC10H13NO2
IUPAC Name

propan-2-yl N-phenylcarbamate

InChI Key

VXPLXMJHHKHSOA-UHFFFAOYSA-N

InChI

InChI=1S/C10H13NO2/c1-8(2)13-10(12)11-9-6-4-3-5-7-9/h3-8H,1-2H3,(H,11,12)

Canonical SMILES

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

Isomeric SMILES

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

Synonyms
        
            Prophame
        
            Propham
        
            Isopropyl phenylcarbamate
        
            122-42-9
        
            Isopropyl N-phenylcarbamate
        
            Triherbide
        
            Agermin
        
            Collavin
        
            Tuberit
        
            Tuberite
        
Classifies
                

                  
                    Veterinary Drug
                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassPhenylcarbamic acid esters
Intermediate Tree NodesNot available
Direct ParentPhenylcarbamic acid esters
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsPhenylcarbamic acid ester - Carbamic acid ester - Carbonic acid derivative - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Carbonyl group - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as phenylcarbamic acid esters. These are ester derivatives of phenylcarbamic acids.

Properties

Property NameProperty Value
Molecular Weight179.219
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count3
Complexity162
Monoisotopic Mass179.095
Exact Mass179.095
XLogP2.6
Formal Charge0
Heavy Atom Count13
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+0.9858
Human Intestinal AbsorptionHIA+1.0000
Caco-2 PermeabilityCaco2+0.7778
P-glycoprotein SubstrateNon-substrate0.8769
P-glycoprotein InhibitorNon-inhibitor0.9210
Non-inhibitor0.8707
Renal Organic Cation TransporterNon-inhibitor0.9332
Distribution
Subcellular localizationMitochondria0.7418
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7818
CYP450 2D6 SubstrateNon-substrate0.6347
CYP450 3A4 SubstrateNon-substrate0.5209
CYP450 1A2 InhibitorInhibitor0.7204
CYP450 2C9 InhibitorNon-inhibitor0.8452
CYP450 2D6 InhibitorNon-inhibitor0.9267
CYP450 2C19 InhibitorNon-inhibitor0.8380
CYP450 3A4 InhibitorNon-inhibitor0.9681
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.6105
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9645
Non-inhibitor0.9599
AMES ToxicityNon AMES toxic0.7174
CarcinogensNon-carcinogens0.6233
Fish ToxicityHigh FHMT0.8744
Tetrahymena Pyriformis ToxicityHigh TPT0.9035
Honey Bee ToxicityHigh HBT0.6172
BiodegradationNot ready biodegradable0.5915
Acute Oral ToxicityIII0.7990
Carcinogenicity (Three-class)Non-required0.6706

Model Value Unit
Absorption
Aqueous solubility-2.1486LogS
Caco-2 Permeability1.7896LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.2222LD50, mol/kg
Fish Toxicity1.5073pLC50, mg/L
Tetrahymena Pyriformis Toxicity-0.1733pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Aril spices0870000European Union0.05*30/12/2015
Mace0870010European Union0.05*30/12/2015
Bud spices0850000European Union0.05*30/12/2015
Cloves (Cassia buds, Cassia buds, Cassia buds,)0850010European Union0.05*30/12/2015
Capers (Nasturtium pods, Nasturtium pods,)0850020European Union0.05*30/12/2015
Others (2)0850990European Union0.05*30/12/2015
Flower pistil spices0860000European Union0.05*30/12/2015
Saffron0860010European Union0.05*30/12/2015
Others (2)0860990European Union0.05*30/12/2015
Others (2)0870990European Union0.05*30/12/2015
(a) swine (Wild boar (farmed),)1011000European Union0.01*30/12/2015
Muscle1011010European Union0.01*30/12/2015
Fat1011020European Union0.01*30/12/2015
Liver1011030European Union0.01*30/12/2015
Kidney1011040European Union0.01*30/12/2015
Edible offals (other than liver and kidney)1011050European Union0.01*30/12/2015
Others (2)1011990European Union0.01*30/12/2015
Muscle1012010European Union0.01*30/12/2015
Fat1012020European Union0.01*30/12/2015
Liver1012030European Union0.01*30/12/2015

References

TitleJournalDatePubmed ID
Pesticide residues in propolis from Spain and Chile. An approach using nearinfrared spectroscopy.Talanta2017 Apr 128153295
A pilot survey of 39 Victorian WWTP effluents using a high speed luminescent umu test in conjunction with a novel GC-MS-database technique for automaticidentification of micropollutants.Water Sci Technol201222766865
Determination of plant resistance to carbamate herbicidal compounds inhibitingcell division and early growth by seed and plantlets bioassays.Nat Protoc200617406469
Determination of imidacloprid, metalaxyl, myclobutanil, propham, andthiabendazole in fruits and vegetables by liquid chromatography-atmosphericpressure chemical ionization-mass spectrometry.Fresenius J Anal Chem2001 Sep11678189
Comparison of an HPTLC and an HPLC procedure for the determination ofchlorpropham, propham and thiabendazole residues in potatoes.Food Addit Contam1991 Sep-Oct1818834

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