Basic Info

Common NameChlorprocarb(F03980)
2D Structure
Description

Chlorprocarb 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 IDF03980
CAS Number23121-99-5
PubChem CID26183
FormulaC13H18N2O4
IUPAC Name

[3-(methoxycarbonylamino)phenyl] N-butylcarbamate

InChI Key

JGNLKFYGXRGIMJ-UHFFFAOYSA-N

InChI

InChI=1S/C13H18N2O4/c1-3-4-8-14-12(16)19-11-7-5-6-10(9-11)15-13(17)18-2/h5-7,9H,3-4,8H2,1-2H3,(H,14,16)(H,15,17)

Canonical SMILES

CCCCNC(=O)OC1=CC=CC(=C1)NC(=O)OC

Isomeric SMILES

CCCCNC(=O)OC1=CC=CC(=C1)NC(=O)OC

Synonyms
        
            Methyl m-hydroxycarbanilate, butylcarbamate
        
            13684-36-1
        
            NSC 222534
        
            BRN 2419804
        
            CARBANILIC ACID, m-HYDROXY-, METHYL ESTER, BUTYLCARBAMATE (ester)
        
            Carbanilic acid, m-hydroxy-, methyl ester, butylcarbamate
        
            [3-(methoxycarbonylamino)phenyl] N-butylcarbamate
        
            Methyl m-hydroxycarbanilate butylcarbamate
        
            AC1L1ALL
        
            WLN: 4MVOR CMVO1
        
Classifies
                

                  
                    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 - Phenoxy compound - 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 Weight266.297
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count7
Complexity296
Monoisotopic Mass266.127
Exact Mass266.127
XLogP2.8
Formal Charge0
Heavy Atom Count19
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+0.9150
Human Intestinal AbsorptionHIA+0.9894
Caco-2 PermeabilityCaco2+0.5053
P-glycoprotein SubstrateSubstrate0.5324
P-glycoprotein InhibitorNon-inhibitor0.8625
Non-inhibitor0.8183
Renal Organic Cation TransporterNon-inhibitor0.8927
Distribution
Subcellular localizationMitochondria0.7113
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8124
CYP450 2D6 SubstrateNon-substrate0.6938
CYP450 3A4 SubstrateNon-substrate0.5236
CYP450 1A2 InhibitorNon-inhibitor0.5292
CYP450 2C9 InhibitorNon-inhibitor0.8870
CYP450 2D6 InhibitorNon-inhibitor0.8372
CYP450 2C19 InhibitorNon-inhibitor0.6312
CYP450 3A4 InhibitorNon-inhibitor0.9246
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8552
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.8981
Non-inhibitor0.8848
AMES ToxicityNon AMES toxic0.5351
CarcinogensNon-carcinogens0.8622
Fish ToxicityHigh FHMT0.9807
Tetrahymena Pyriformis ToxicityHigh TPT0.9520
Honey Bee ToxicityLow HBT0.6030
BiodegradationNot ready biodegradable0.8436
Acute Oral ToxicityIII0.6536
Carcinogenicity (Three-class)Non-required0.6513

Model Value Unit
Absorption
Aqueous solubility-3.7877LogS
Caco-2 Permeability0.8090LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.2002LD50, mol/kg
Fish Toxicity1.1959pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.2840pIGC50, 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