Propamocarb

Basic Info

Common NamePropamocarb(F04023)
2D Structure
Description

Propamocarb 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 IDF04023
CAS Number24579-73-5
PubChem CID32490
FormulaC9H20N2O2
IUPAC Name

propyl N-[3-(dimethylamino)propyl]carbamate

InChI Key

WZZLDXDUQPOXNW-UHFFFAOYSA-N

InChI

InChI=1S/C9H20N2O2/c1-4-8-13-9(12)10-6-5-7-11(2)3/h4-8H2,1-3H3,(H,10,12)

Canonical SMILES

CCCOC(=O)NCCCN(C)C

Isomeric SMILES

CCCOC(=O)NCCCN(C)C

Synonyms
        
            PROPAMOCARB
        
            24579-73-5
        
            Propamocarbe
        
            Propyl (3-(dimethylamino)propyl)carbamate
        
            UNII-8HLL7N9UWO
        
            Propamocarbe [ISO-French]
        
            Nor-AM 39744
        
            Propamocarb [ANSI:BSI:ISO]
        
            8HLL7N9UWO
        
            BRN 2080745
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
SubclassAmino acids, peptides, and analogues
Intermediate Tree NodesAmino acids and derivatives - Carbamic acids and derivatives
Direct ParentCarbamate esters
Alternative Parents
Molecular FrameworkAliphatic acyclic compounds
SubstituentsCarbamic acid ester - Tertiary aliphatic amine - Tertiary amine - Carbonic acid derivative - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Carbonyl group - Amine - Aliphatic acyclic compound
DescriptionThis compound belongs to the class of organic compounds known as carbamate esters. These are compounds containing an ester of carbamic acid with the general structure R2NC(=O)OR' (R' not H). They are esters of carbamic acids.

Properties

Property NameProperty Value
Molecular Weight188.271
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count7
Complexity138
Monoisotopic Mass188.152
Exact Mass188.152
XLogP1.2
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+0.9721
Human Intestinal AbsorptionHIA+0.9950
Caco-2 PermeabilityCaco2+0.5316
P-glycoprotein SubstrateNon-substrate0.5519
P-glycoprotein InhibitorInhibitor0.5137
Non-inhibitor0.8291
Renal Organic Cation TransporterNon-inhibitor0.8315
Distribution
Subcellular localizationLysosome0.6756
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8255
CYP450 2D6 SubstrateNon-substrate0.7483
CYP450 3A4 SubstrateNon-substrate0.5098
CYP450 1A2 InhibitorNon-inhibitor0.7261
CYP450 2C9 InhibitorNon-inhibitor0.8681
CYP450 2D6 InhibitorNon-inhibitor0.8722
CYP450 2C19 InhibitorNon-inhibitor0.8701
CYP450 3A4 InhibitorNon-inhibitor0.9587
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9446
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9498
Non-inhibitor0.7998
AMES ToxicityNon AMES toxic0.7571
CarcinogensNon-carcinogens0.6154
Fish ToxicityHigh FHMT0.7756
Tetrahymena Pyriformis ToxicityLow TPT0.5229
Honey Bee ToxicityLow HBT0.5514
BiodegradationNot ready biodegradable0.8034
Acute Oral ToxicityIII0.6280
Carcinogenicity (Three-class)Non-required0.6236
Model Value Unit
Absorption
Aqueous solubility-2.0960LogS
Caco-2 Permeability1.1590LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.3627LD50, mol/kg
Fish Toxicity1.7787pLC50, mg/L
Tetrahymena Pyriformis Toxicity-0.2827pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
CarrotItaly10mg/kg
PeelItaly10mg/kg
CeleryItaly10mg/kg
LettuceItaly10mg/kg
OnionItaly10mg/kg
Others (2)0140990European Union0.01*26/06/2018
Dewberries (Boysenberries, Loganberries, Olallieberries, Salmonberries, Tayberries, Thimbleberries, Youngberries, Other species and hybrids of genus Rubus, not elsewhere mentioned,)0153020European Union0.01*26/06/2018
Blueberries (Aronia berries/chokeberries (black, purple and red), Aronia berries/chokeberries (black, purple and red), Aronia berries/chokeberries (black, purple and red), Bearberries, Bilberries/E...0154010European Union0.01*26/06/2018
Guavas (Brazilian guavas, Cattley guavas, Costarican guavas, Guayabillos, Parà guavas,)0163070European Union0.01*26/06/2018
Cassava roots/manioc (Blue taros/blue tannias, Canna, Chayotes/christophines roots, Dasheen taros, Eddoe taros, Konjac roots, Tannias/arrowleaf elephant ears/tajer,)0212010European Union0.01*26/06/2018
Chinese cabbages/pe-tsai (Chinese flat cabbages/tatsoi/tai goo choi, Indian mustards/mustard greens, Komatsuna/mustard spinaches, Mizuna (4), Pak-choi/paksoi, Turnip greens/turnip tops (5), Seakale,)0243010European Union2026/06/2018
Kales (Borecoles/collards greens/curly kales, Cow cabbages/stem kales, Cow cabbages/Jersey kales, Kohlrabies leaves (6), Rape kales/Siberian kales, Portuguese kales/tronchuda kales/Portuguese cabba...0243020European Union2026/06/2018
Basil and edible flowers (Apple mint, Asiatic pennywort, Bergamot mint/eau-de-Cologne mint, Corsican mint, Courgette (edible flowers), Gingermint, Greek bush basil, Hoary basil, Holy basil/tulsi, L...0256080European Union3026/06/2018
Pine nut kernels (Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels ...0120090European Union0.01*26/06/2018
FRUITS, FRESH or FROZEN; TREE NUTS0100000European Union0.01*26/06/2018
Citrus fruits0110000European Union0.01*26/06/2018
Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,)0110010European Union0.01*26/06/2018
Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,)0110020European Union0.01*26/06/2018
Lemons (Buddha's hands/Buddha's fingers, Citrons,)0110030European Union0.01*26/06/2018
Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,)0110040European Union0.01*26/06/2018

References

TitleJournalDatePubmed ID
Residue Analysis of 60 Pesticides in Red Swamp Crayfish Using QuEChERS withHigh-Performance Liquid Chromatography-Tandem Mass Spectrometry.J Agric Food Chem2018 May 2329364652
Pesticide Residues on Three Cut Flower Species and Potential Exposure of Floristsin Belgium.Int J Environ Res Public Health2016 Sep 2327669276
Multilocation field trials for risk assessment of a combination fungicideFluopicolide + Propamocarb in tomato.Environ Monit Assess2016 Nov27709463
Detection and assessment of chemical hormesis on the radial growth in vitro ofoomycetes and fungal plant pathogens.Dose Response2012 Sep 2923983664
[Rapid determination of 6 pesticide residues in tomato paste by ultra performanceliquid chromatography-tandem mass spectrometry].Se Pu2011 Nov22393693

Targets

Target Details

Acetylcholinesterase

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
Target Details

Cholinesterase

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