Aldicarb

Basic Info

Common NameAldicarb(F03953)
2D Structure
Description

Aldicarb is a carbamate pesticide. Aldicarb is a carbamate insecticide. 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. Aldicarb is effective against thrips, aphids, spider mites, lygus, fleahoppers, and leafminers, but is primarily used as a nematicide. Aldicarb is effective where resistance to organophosphate insecticides has developed, and is extremely important in potato production, where it is used for the control of soil-borne nematodes and some foliar pests. Its weakness is its high level of solubility, which restricts its use in certain areas where the water table is close to the surface. Most of the carbamates are extremely toxic to Hymenoptera, and precautions must be taken to avoid exposure to foraging bees or parasitic wasps. Aldicarb was one of the 'dirty dozen' pesticides that the environmental group Pesticide Action Network North America targeted in 1985. EPA put a ban in place in 2010, requiring an end to distribution by 2017. Use on citrus and potatoes is banned beginning in 2012, with a complete ban in place by 2018.

FRCD IDF03953
CAS Number116-06-3
PubChem CID9570071
FormulaC7H14N2O2S
IUPAC Name

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

InChI Key

QGLZXHRNAYXIBU-WEVVVXLNSA-N

InChI

InChI=1S/C7H14N2O2S/c1-7(2,12-4)5-9-11-6(10)8-3/h5H,1-4H3,(H,8,10)/b9-5+

Canonical SMILES

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

Isomeric SMILES

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

Synonyms
        
            aldicarb
        
            Temik
        
            Aldicarbe
        
            116-06-3
        
            Temik 10 G
        
            NSC 379586
        
            UC-21149
        
            2-Methyl-2-(methylthio)propionaldehyde O-(methylcarbamoyl)oxime
        
            Temik G 10
        
            OMS-771
Classifies
                

                  
                    Pollutant
                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic acids and derivatives
ClassCarboximidic acids and derivatives
SubclassNot available
Intermediate Tree NodesNot available
Direct ParentCarboximidic acids and derivatives
Alternative Parents
Molecular FrameworkAliphatic acyclic compounds
SubstituentsDialkylthioether - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Sulfenyl compound - Thioether - Carboximidic acid derivative - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Hydrocarbon derivative - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Imine - Aliphatic acyclic compound
DescriptionThis compound belongs to the class of organic compounds known as carboximidic acids and derivatives. These are compounds containing a carboximidic group, with the general formula R-C(=NR1)OR2.

Properties

Property NameProperty Value
Molecular Weight190.261
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count4
Complexity180
Monoisotopic Mass190.078
Exact Mass190.078
XLogP1.1
Formal Charge0
Heavy Atom Count12
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+0.9297
Human Intestinal AbsorptionHIA+0.9965
Caco-2 PermeabilityCaco2-0.5292
P-glycoprotein SubstrateNon-substrate0.7968
P-glycoprotein InhibitorNon-inhibitor0.8565
Non-inhibitor0.9115
Renal Organic Cation TransporterNon-inhibitor0.9504
Distribution
Subcellular localizationMitochondria0.6754
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7532
CYP450 2D6 SubstrateNon-substrate0.8792
CYP450 3A4 SubstrateNon-substrate0.5755
CYP450 1A2 InhibitorNon-inhibitor0.6683
CYP450 2C9 InhibitorNon-inhibitor0.7643
CYP450 2D6 InhibitorNon-inhibitor0.8994
CYP450 2C19 InhibitorNon-inhibitor0.6557
CYP450 3A4 InhibitorNon-inhibitor0.9508
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8529
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9966
Non-inhibitor0.9657
AMES ToxicityNon AMES toxic0.9133
CarcinogensCarcinogens 0.5271
Fish ToxicityHigh FHMT0.7423
Tetrahymena Pyriformis ToxicityLow TPT0.6274
Honey Bee ToxicityHigh HBT0.8831
BiodegradationNot ready biodegradable1.0000
Acute Oral ToxicityI0.7797
Carcinogenicity (Three-class)Non-required0.6928
Model Value Unit
Absorption
Aqueous solubility-1.0724LogS
Caco-2 Permeability1.3694LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity5.1054LD50, mol/kg
Fish Toxicity0.0602pLC50, mg/L
Tetrahymena Pyriformis Toxicity-0.2659pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Peanuts/groundnuts0401020European Union0.05*21/10/2011
Citrus fruits0110000European Union0.02*21/10/2011
Mulberries (black and white)0154060European Union0.02*21/10/2011
Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,)0110020European Union0.02*21/10/2011
Lemons (Buddha's hands/Buddha's fingers, Citrons,)0110030European Union0.02*21/10/2011
Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,)0110040European Union0.02*21/10/2011
Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,)0110050European Union0.02*21/10/2011
Others (2)0110990European Union0.02*21/10/2011
Tree nuts0120000European Union0.05*21/10/2011
Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,)0120010European Union0.05*21/10/2011
Brazil nuts0120020European Union0.05*21/10/2011
Cashew nuts0120030European Union0.05*21/10/2011
Chestnuts0120040European Union0.05*21/10/2011
Coconuts (Areca nuts/betel nuts,)0120050European Union0.05*21/10/2011
Hazelnuts/cobnuts (Acorns, Filberts,)0120060European Union0.05*21/10/2011
Macadamias0120070European Union0.05*21/10/2011
Pecans (Hickory nuts,)0120080European Union0.05*21/10/2011
Pistachios0120100European Union0.05*21/10/2011
Walnuts0120110European Union0.05*21/10/2011
Others (2)0120990European Union0.05*21/10/2011

References

TitleJournalDatePubmed ID
Recent trends of modern bacterial insecticides for pest control practice inintegrated crop management system.3 Biotech2017 May28444605
Fluorescence biosensing strategy based on mercury ion-mediated DNA conformationalswitch and nicking enzyme-assisted cycling amplification for highly sensitivedetection of carbamate pesticide.Biosens Bioelectron2016 Mar 1526492468
Death by chumbinho: aldicarb intoxication-regarding a corpse in decomposition.Int J Legal Med2016 Jul26914800
Suspected poisoning of domestic animals by pesticides.Sci Total Environ2016 Jan 126367188
Multiresidue method for the quantitation of 20 pesticides in aquatic products.Anal Bioanal Chem2015 Dec26466578
Cholinesterase sensor based on glassy carbon electrode modified with Agnanoparticles decorated with macrocyclic ligands.Talanta2014 Sep24913851
New validated multiresidue analysis of six 4-hydroxy-coumarin anticoagulantrodenticides in hen eggs.J Vet Diagn Invest2013 Nov24081927
Effects of aldicarb and neonicotinoid seed treatments on twospotted spider miteon cotton.J Econ Entomol2013 Apr23786068
Aldicarb: a case series of watermelon-borne carbamate toxicity.J Agromedicine201323540307
[Determination of aldicarb and its metabolites in peanuts by high performanceliquid chromatography-linear ion trap triple stage mass spectrometry].Se Pu2012 Mar22715699
A semi-fluid gellan gum medium improves nematode toxicity testing.Ecotoxicol Environ Saf2011 Oct21784524
Dispersive liquid-liquid microextraction coupled with high-performance liquidchromatography-diode array detection for the determination of N-methyl carbamate pesticides in vegetables.J Sep Sci2011 Jan21246726
The ameliorative and toxic effects of selenite on Caenorhabditis elegans.Food Chem Toxicol2011 Apr21145367
Solid-phase extraction for multi-residue analysis of pesticides in honey.J Environ Sci Health B201120936565
Development of a simple and low-cost enzymatic methodology for quantitativeanalysis of carbamates in meat samples of forensic interest.J Forensic Sci2010 May20345797
High levels of miticides and agrochemicals in North American apiaries:implications for honey bee health.PLoS One2010 Mar 1920333298
Effects of aldicarb and propoxur on cytotoxicity and lipid peroxidation in CHO-K1cells.Food Chem Toxicol2010 Jun20346998
Electrospray ionization matrix effect as an uncertainty source in HPLC/ESI-MSpesticide residue analysis.J AOAC Int2010 Jan-Feb20334192
Multiresidue analysis of pesticides with hydrolyzable functionality in cookedvegetables by liquid chromatography tandem mass spectrometry.Biomed Chromatogr2009 Jul19360753
Rate, placement and timing of aldicarb applications to control Asian citruspsyllid, Diaphorina citri Kuwayama (Hemiptera: Psyllidae), in oranges.Pest Manag Sci2008 Nov18537108