Basic Info

Common NameDioxacarb(F03991)
2D Structure
Description

Dioxacarb 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 IDF03991
CAS Number6988-21-2
PubChem CID23421
FormulaC11H13NO4
IUPAC Name

[2-(1,3-dioxolan-2-yl)phenyl] N-methylcarbamate

InChI Key

SDKQRNRRDYRQKY-UHFFFAOYSA-N

InChI

InChI=1S/C11H13NO4/c1-12-11(13)16-9-5-3-2-4-8(9)10-14-6-7-15-10/h2-5,10H,6-7H2,1H3,(H,12,13)

Canonical SMILES

CNC(=O)OC1=CC=CC=C1C2OCCO2

Isomeric SMILES

CNC(=O)OC1=CC=CC=C1C2OCCO2

Synonyms
        
            Famid
        
            DIOXACARB
        
            Dioxacarbe
        
            Dioxocarb
        
            Rovlinka
        
            Elocron
        
            Elocron 50WP
        
            MCDP
        
            Elocron 8353
        
            6988-21-2
        
Classifies
                

                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassPhenoxy compounds
Intermediate Tree NodesNot available
Direct ParentPhenoxy compounds
Alternative Parents
Molecular FrameworkAromatic heteromonocyclic compounds
SubstituentsPhenoxy compound - Meta-dioxolane - Acetal - Carboximidic acid derivative - Propargyl-type 1,3-dipolar organic compound - Oxacycle - Organoheterocyclic compound - Organic 1,3-dipolar compound - Organic nitrogen compound - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Imine - Organopnictogen compound - Organic oxygen compound - Aromatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as phenoxy compounds. These are aromatic compounds contaning a phenoxy group.

Properties

Property NameProperty Value
Molecular Weight223.228
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count3
Complexity240
Monoisotopic Mass223.084
Exact Mass223.084
XLogP0.5
Formal Charge0
Heavy Atom Count16
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+0.9404
Human Intestinal AbsorptionHIA+0.9966
Caco-2 PermeabilityCaco2+0.5770
P-glycoprotein SubstrateNon-substrate0.7819
P-glycoprotein InhibitorNon-inhibitor0.8238
Non-inhibitor0.8694
Renal Organic Cation TransporterNon-inhibitor0.8308
Distribution
Subcellular localizationMitochondria0.7962
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7674
CYP450 2D6 SubstrateNon-substrate0.7662
CYP450 3A4 SubstrateSubstrate0.5313
CYP450 1A2 InhibitorInhibitor0.7509
CYP450 2C9 InhibitorNon-inhibitor0.5981
CYP450 2D6 InhibitorNon-inhibitor0.8225
CYP450 2C19 InhibitorInhibitor0.6365
CYP450 3A4 InhibitorNon-inhibitor0.7986
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.5898
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9518
Non-inhibitor0.9329
AMES ToxicityNon AMES toxic0.6591
CarcinogensNon-carcinogens0.9438
Fish ToxicityHigh FHMT0.7561
Tetrahymena Pyriformis ToxicityHigh TPT0.9953
Honey Bee ToxicityLow HBT0.5000
BiodegradationNot ready biodegradable0.6490
Acute Oral ToxicityI0.7734
Carcinogenicity (Three-class)Non-required0.5064

Model Value Unit
Absorption
Aqueous solubility-1.6326LogS
Caco-2 Permeability1.2061LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity3.9196LD50, mol/kg
Fish Toxicity1.0539pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.2548pIGC50, ug/L

References

TitleJournalDatePubmed ID
Liquid chromatographic determination of N-methylcarbamate insecticides and metabolites in crops. II. Analytical characteristics and residue findings.J Assoc Off Anal Chem1985 Jul-Aug4030646

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