Basic Info

Common NameAldoxycarb(F03954)
2D Structure
Description

Aldoxycarb 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 IDF03954
CAS Number1646-88-4
PubChem CID9570093
FormulaC7H14N2O4S
IUPAC Name

[(E)-(2-methyl-2-methylsulfonylpropylidene)amino] N-methylcarbamate

InChI Key

YRRKLBAKDXSTNC-WEVVVXLNSA-N

InChI

InChI=1S/C7H14N2O4S/c1-7(2,14(4,11)12)5-9-13-6(10)8-3/h5H,1-4H3,(H,8,10)/b9-5+

Canonical SMILES

CC(C)(C=NOC(=O)NC)S(=O)(=O)C

Isomeric SMILES

CC(C)(/C=N/OC(=O)NC)S(=O)(=O)C

Synonyms
        
            Aldicarb (sulfone)
        
            Aldoxycarb
        
            Standak
        
            Sulfocarb
        
            Aldicarb-sulfone
        
            ALDICARB SULFONE
        
            1646-88-4
        
            Caswell No. 011AA
        
            Temik sulfone
        
            Aldoxycarbe [ISO-French]
        
Classifies
                

                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganosulfur compounds
ClassSulfonyls
SubclassSulfones
Intermediate Tree NodesNot available
Direct ParentSulfones
Alternative Parents
Molecular FrameworkAliphatic acyclic compounds
SubstituentsSulfone - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Carboximidic acid derivative - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Imine - Aliphatic acyclic compound
DescriptionThis compound belongs to the class of organic compounds known as sulfones. These are compounds containing a sulfonyl group( which as the general structure RS(=O)2R' (R,R' =alkyl, aryl)) attached to two carbon atoms.

Properties

Property NameProperty Value
Molecular Weight222.259
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count5
Rotatable Bond Count4
Complexity326
Monoisotopic Mass222.067
Exact Mass222.067
XLogP-0.6
Formal Charge0
Heavy Atom Count14
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.7662
Human Intestinal AbsorptionHIA+0.9726
Caco-2 PermeabilityCaco2-0.5770
P-glycoprotein SubstrateNon-substrate0.8170
P-glycoprotein InhibitorNon-inhibitor0.8781
Non-inhibitor0.8588
Renal Organic Cation TransporterNon-inhibitor0.9587
Distribution
Subcellular localizationMitochondria0.6072
Metabolism
CYP450 2C9 SubstrateNon-substrate0.6339
CYP450 2D6 SubstrateNon-substrate0.8261
CYP450 3A4 SubstrateNon-substrate0.5859
CYP450 1A2 InhibitorNon-inhibitor0.7670
CYP450 2C9 InhibitorNon-inhibitor0.7381
CYP450 2D6 InhibitorNon-inhibitor0.8927
CYP450 2C19 InhibitorNon-inhibitor0.5886
CYP450 3A4 InhibitorNon-inhibitor0.9510
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9568
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9946
Non-inhibitor0.9374
AMES ToxicityNon AMES toxic0.5655
CarcinogensCarcinogens 0.6113
Fish ToxicityHigh FHMT0.9147
Tetrahymena Pyriformis ToxicityLow TPT0.6460
Honey Bee ToxicityHigh HBT0.7397
BiodegradationNot ready biodegradable0.9963
Acute Oral ToxicityI0.7734
Carcinogenicity (Three-class)Non-required0.6511

Model Value Unit
Absorption
Aqueous solubility-1.9136LogS
Caco-2 Permeability0.7392LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity4.0772LD50, mol/kg
Fish Toxicity0.8794pLC50, mg/L
Tetrahymena Pyriformis Toxicity-0.0427pIGC50, ug/L

References

TitleJournalDatePubmed ID
[Determination of aldicarb and its metabolites in peanuts by high performanceliquid chromatography-linear ion trap triple stage mass spectrometry].Se Pu2012 Mar22715699
[Behavior of N-methylcarbamate pesticides during refinement processing of edible oils].J Oleo Sci200717898465
N-methyl carbamate pesticide residues in conventional and organic infant foodsavailable on the Canadian retail market, 2001-03.Food Addit Contam2006 Jul16751141
Pulsed losses and degradation of aldicarb in a South Florida agriculturalwatershed.Arch Environ Contam Toxicol2005 Jan15657802
Determination of pesticides in apple-based infant foods using liquidchromatography electrospray ionization tandem mass spectrometry.J Agric Food Chem2005 Feb 915686398
Determination of aldicarb, aldicarb sulfoxide and aldicarb sulfone in some fruitsand vegetables using high-performance liquid chromatography-atmospheric pressure chemical ionization mass spectrometry.J Chromatogr A2000 Aug 410949478
Analyte stability study of N-methylcarbamate pesticides in beef and poultry livertissues by liquid chromatography.J AOAC Int1993 Nov-Dec8286970
Simplified multiresidue method for liquid chromatographic determination ofN-methyl carbamate insecticides in fruits and vegetables.J Assoc Off Anal Chem1988 May-Jun3391959

Targets

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
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