Basic Info

Common NameDimetan(F03989)
2D Structure
Description

Dimetan 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 IDF03989
CAS Number122-15-6
PubChem CID31201
FormulaC11H17NO3
IUPAC Name

(5,5-dimethyl-3-oxocyclohexen-1-yl) N,N-dimethylcarbamate

InChI Key

ITEQSCBLCCNACE-UHFFFAOYSA-N

InChI

InChI=1S/C11H17NO3/c1-11(2)6-8(13)5-9(7-11)15-10(14)12(3)4/h5H,6-7H2,1-4H3

Canonical SMILES

CC1(CC(=CC(=O)C1)OC(=O)N(C)C)C

Isomeric SMILES

CC1(CC(=CC(=O)C1)OC(=O)N(C)C)C

Synonyms
        
            215ZV6RPXL
        
            DIMETAN
        
            Geigy 19258
        
            UNII-215ZV6RPXL
        
            122-15-6
        
            EINECS 204-525-8
        
            ENT 24,728
        
            BRN 3280184
        
            5,5-Dimethyl-3-oxocyclohex-1-enyl dimethylcarbamate
        
            AI3-24728
        
Classifies
                

                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds
SubclassCarbonyl compounds
Intermediate Tree NodesKetones - Cyclic ketones
Direct ParentCyclohexenones
Alternative Parents
Molecular FrameworkAliphatic homomonocyclic compounds
SubstituentsCyclohexenone - Carbamic acid ester - Enol ester - Carbonic acid derivative - Organic nitrogen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organonitrogen compound - Aliphatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as cyclohexenones. These are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Properties

Property NameProperty Value
Molecular Weight211.261
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count3
Rotatable Bond Count2
Complexity316
Monoisotopic Mass211.121
Exact Mass211.121
XLogP1.2
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+0.9381
Human Intestinal AbsorptionHIA+0.9974
Caco-2 PermeabilityCaco2+0.5802
P-glycoprotein SubstrateNon-substrate0.7384
P-glycoprotein InhibitorInhibitor0.6016
Non-inhibitor0.9019
Renal Organic Cation TransporterNon-inhibitor0.9045
Distribution
Subcellular localizationMitochondria0.6960
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8270
CYP450 2D6 SubstrateNon-substrate0.8433
CYP450 3A4 SubstrateSubstrate0.6386
CYP450 1A2 InhibitorNon-inhibitor0.8222
CYP450 2C9 InhibitorNon-inhibitor0.8580
CYP450 2D6 InhibitorNon-inhibitor0.8987
CYP450 2C19 InhibitorNon-inhibitor0.7861
CYP450 3A4 InhibitorNon-inhibitor0.8441
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8781
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9596
Non-inhibitor0.9731
AMES ToxicityNon AMES toxic0.6256
CarcinogensNon-carcinogens0.6359
Fish ToxicityHigh FHMT0.8083
Tetrahymena Pyriformis ToxicityHigh TPT0.8694
Honey Bee ToxicityHigh HBT0.8107
BiodegradationNot ready biodegradable0.9773
Acute Oral ToxicityII0.7304
Carcinogenicity (Three-class)Non-required0.5396

Model Value Unit
Absorption
Aqueous solubility-0.9123LogS
Caco-2 Permeability1.4343LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity3.2143LD50, mol/kg
Fish Toxicity1.1000pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.1744pIGC50, 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