Basic Info

Common NameCarbasulam(F03973)
2D Structure
Description

Carbasulam 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 IDF03973
CAS Number1773-37-1
PubChem CID15679
FormulaC10H12N2O6S
IUPAC Name

methyl N-[4-(methoxycarbonylamino)phenyl]sulfonylcarbamate

InChI Key

ZTFLDKYLDUZSMN-UHFFFAOYSA-N

InChI

InChI=1S/C10H12N2O6S/c1-17-9(13)11-7-3-5-8(6-4-7)19(15,16)12-10(14)18-2/h3-6H,1-2H3,(H,11,13)(H,12,14)

Canonical SMILES

COC(=O)NC1=CC=C(C=C1)S(=O)(=O)NC(=O)OC

Isomeric SMILES

COC(=O)NC1=CC=C(C=C1)S(=O)(=O)NC(=O)OC

Synonyms
        
            methyl N-[4-(methoxycarbonylamino)phenyl]sulfonylcarbamate
        
            Carbasulam
        
            1773-37-1
        
            UNII-37T3H0AML4
        
            37T3H0AML4
        
            Acetylasulam
        
            Carbamic acid, [[4-[(methoxycarbonyl)amino]phenyl]sulfonyl]-, methyl ester
        
            Carbasulam [ISO]
        
            Caswell No. 573I
        
            Carbamic acid, ((4-((methoxycarbonyl)amino)phenyl)sulfonyl)-, methyl ester
        
Classifies
                

                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassPhenylcarbamic acid esters
Intermediate Tree NodesNot available
Direct ParentPhenylcarbamic acid esters
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsPhenylcarbamic acid ester - Benzenesulfonamide - Benzenesulfonyl group - Organic sulfonic acid or derivatives - Organosulfonic acid or derivatives - Sulfonyl - Carbamic acid ester - Aminosulfonyl compound - Carbonic acid derivative - Carbonyl group - Organic nitrogen compound - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Hydrocarbon derivative - Organic oxygen compound - Organic oxide - Organopnictogen compound - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as phenylcarbamic acid esters. These are ester derivatives of phenylcarbamic acids.

Properties

Property NameProperty Value
Molecular Weight288.274
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count5
Complexity422
Monoisotopic Mass288.042
Exact Mass288.042
XLogP0
Formal Charge0
Heavy Atom Count19
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+0.9445
Human Intestinal AbsorptionHIA+0.8965
Caco-2 PermeabilityCaco2-0.5965
P-glycoprotein SubstrateNon-substrate0.8781
P-glycoprotein InhibitorNon-inhibitor0.9304
Non-inhibitor0.7803
Renal Organic Cation TransporterNon-inhibitor0.9531
Distribution
Subcellular localizationMitochondria0.6280
Metabolism
CYP450 2C9 SubstrateNon-substrate0.6504
CYP450 2D6 SubstrateNon-substrate0.8710
CYP450 3A4 SubstrateNon-substrate0.7166
CYP450 1A2 InhibitorNon-inhibitor0.9160
CYP450 2C9 InhibitorInhibitor0.6645
CYP450 2D6 InhibitorNon-inhibitor0.9151
CYP450 2C19 InhibitorInhibitor0.6628
CYP450 3A4 InhibitorNon-inhibitor0.8872
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.6504
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9905
Non-inhibitor0.9591
AMES ToxicityNon AMES toxic0.7863
CarcinogensNon-carcinogens0.7663
Fish ToxicityHigh FHMT0.9641
Tetrahymena Pyriformis ToxicityHigh TPT0.6034
Honey Bee ToxicityLow HBT0.6424
BiodegradationNot ready biodegradable1.0000
Acute Oral ToxicityIII0.7604
Carcinogenicity (Three-class)Non-required0.5848

Model Value Unit
Absorption
Aqueous solubility-2.0181LogS
Caco-2 Permeability0.6437LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.2083LD50, mol/kg
Fish Toxicity1.7221pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.0805pIGC50, 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