Basic Info

Common NameSwep(F04029)
2D Structure
Description

Swep 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 IDF04029
CAS Number1918-18-9
PubChem CID15969
FormulaC8H7Cl2NO2
IUPAC Name

methyl N-(3,4-dichlorophenyl)carbamate

InChI Key

WOZQBERUBLYCEG-UHFFFAOYSA-N

InChI

InChI=1S/C8H7Cl2NO2/c1-13-8(12)11-5-2-3-6(9)7(10)4-5/h2-4H,1H3,(H,11,12)

Canonical SMILES

COC(=O)NC1=CC(=C(C=C1)Cl)Cl

Isomeric SMILES

COC(=O)NC1=CC(=C(C=C1)Cl)Cl

Synonyms
        
            Methyl 3,4-dichlorophenylcarbamate
        
            SWEP
        
            Methyl N-(3,4-dichlorophenyl)carbamate
        
            1918-18-9
        
            Methyl 3,4-dichlorocarbanilate
        
            Caswell No. 818
        
            Swep [ANSI]
        
            NIA 2995J
        
            Carbamic acid, (3,4-dichlorophenyl)-, methyl ester
        
            FMC 2995
        
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 - 1,2-dichlorobenzene - Chlorobenzene - Halobenzene - Aryl chloride - Aryl halide - Carbamic acid ester - Carbonic acid derivative - Organic nitrogen compound - Organonitrogen compound - Organochloride - Organohalogen compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Carbonyl group - Organic oxygen compound - 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 Weight220.049
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count2
Complexity189
Monoisotopic Mass218.985
Exact Mass218.985
XLogP3.5
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+0.9912
Human Intestinal AbsorptionHIA+0.9957
Caco-2 PermeabilityCaco2+0.7678
P-glycoprotein SubstrateNon-substrate0.8953
P-glycoprotein InhibitorNon-inhibitor0.9557
Non-inhibitor0.9565
Renal Organic Cation TransporterNon-inhibitor0.9233
Distribution
Subcellular localizationMitochondria0.7758
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7326
CYP450 2D6 SubstrateNon-substrate0.7706
CYP450 3A4 SubstrateNon-substrate0.5157
CYP450 1A2 InhibitorInhibitor0.9243
CYP450 2C9 InhibitorNon-inhibitor0.6990
CYP450 2D6 InhibitorNon-inhibitor0.8475
CYP450 2C19 InhibitorNon-inhibitor0.6592
CYP450 3A4 InhibitorNon-inhibitor0.9090
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.6117
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9345
Non-inhibitor0.9580
AMES ToxicityNon AMES toxic0.6670
CarcinogensNon-carcinogens0.7094
Fish ToxicityHigh FHMT0.9546
Tetrahymena Pyriformis ToxicityHigh TPT0.9886
Honey Bee ToxicityLow HBT0.6421
BiodegradationNot ready biodegradable0.9448
Acute Oral ToxicityIII0.8150
Carcinogenicity (Three-class)Non-required0.6603

Model Value Unit
Absorption
Aqueous solubility-3.2171LogS
Caco-2 Permeability1.9042LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.5938LD50, mol/kg
Fish Toxicity1.2745pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.5139pIGC50, 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