Basic Info

Common NameOms 22(F04016)
2D Structure
Description

Oms 22 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 IDF04016
CAS Number3566-09-4
PubChem CID19107
FormulaC11H14ClNO2
IUPAC Name

(2-chloro-3-propan-2-ylphenyl) N-methylcarbamate

InChI Key

OYQYZTQPLCFOSQ-UHFFFAOYSA-N

InChI

InChI=1S/C11H14ClNO2/c1-7(2)8-5-4-6-9(10(8)12)15-11(14)13-3/h4-7H,1-3H3,(H,13,14)

Canonical SMILES

CC(C)C1=C(C(=CC=C1)OC(=O)NC)Cl

Isomeric SMILES

CC(C)C1=C(C(=CC=C1)OC(=O)NC)Cl

Synonyms
        
            Methylcarbamic acid 2-chloro-m-cumenyl ester
        
            Hercules 7522
        
            3566-09-4
        
            ENT 25,711-X
        
            BRN 2976868
        
            2-chloro-3-isopropylphenyl-n-methyl carbamate
        
            2-Chloro-3-(1-methylethyl)phenol methylcarbamate
        
            CARBAMIC ACID, METHYL-, 2-CHLORO-m-CUMENYL ESTER
        
            Oms 22
        
            AC1L2DH0
        
Classifies
                

                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassPhenyl methylcarbamates
Intermediate Tree NodesNot available
Direct ParentPhenyl methylcarbamates
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsPhenyl methylcarbamate - Cumene - Phenylpropane - Phenoxy compound - 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 phenyl methylcarbamates. These are aromatic compounds containing a methylcarbamic acid esterified with a phenyl group.

Properties

Property NameProperty Value
Molecular Weight227.688
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count3
Complexity221
Monoisotopic Mass227.071
Exact Mass227.071
XLogP3.3
Formal Charge0
Heavy Atom Count15
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+0.9705
Human Intestinal AbsorptionHIA+1.0000
Caco-2 PermeabilityCaco2+0.7324
P-glycoprotein SubstrateNon-substrate0.8465
P-glycoprotein InhibitorNon-inhibitor0.9488
Non-inhibitor0.9848
Renal Organic Cation TransporterNon-inhibitor0.9038
Distribution
Subcellular localizationMitochondria0.7754
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7580
CYP450 2D6 SubstrateSubstrate0.5581
CYP450 3A4 SubstrateSubstrate0.6745
CYP450 1A2 InhibitorInhibitor0.8541
CYP450 2C9 InhibitorNon-inhibitor0.7158
CYP450 2D6 InhibitorNon-inhibitor0.8762
CYP450 2C19 InhibitorInhibitor0.6335
CYP450 3A4 InhibitorNon-inhibitor0.8569
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.5660
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9363
Non-inhibitor0.9243
AMES ToxicityAMES toxic0.6893
CarcinogensNon-carcinogens0.7815
Fish ToxicityHigh FHMT0.9660
Tetrahymena Pyriformis ToxicityHigh TPT0.9797
Honey Bee ToxicityHigh HBT0.7635
BiodegradationNot ready biodegradable0.9792
Acute Oral ToxicityI0.7822
Carcinogenicity (Three-class)Non-required0.5790

Model Value Unit
Absorption
Aqueous solubility-3.6123LogS
Caco-2 Permeability1.7829LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity3.1191LD50, mol/kg
Fish Toxicity0.5857pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.6960pIGC50, 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