Basic Info

Common NameCarboxazole(F03978)
2D Structure
Description

Carboxazole 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 IDF03978
CAS Number55808-13-4
PubChem CID13309592
FormulaC9H14N2O3
IUPAC Name

methyl N-(5-tert-butyl-1,2-oxazol-3-yl)carbamate

InChI Key

ZGUYPJJFHYFLBV-UHFFFAOYSA-N

InChI

InChI=1S/C9H14N2O3/c1-9(2,3)6-5-7(11-14-6)10-8(12)13-4/h5H,1-4H3,(H,10,11,12)

Canonical SMILES

CC(C)(C)C1=CC(=NO1)NC(=O)OC

Isomeric SMILES

CC(C)(C)C1=CC(=NO1)NC(=O)OC

Synonyms
        
            DTXSID10204390
        
            Carboxazole [ISO]
        
            UNII-HWU9B4W5EA
        
            HWU9B4W5EA
        
            55808-13-4
        
            Carboxazole
        
            SCHEMBL164064
        
            CTK1F5993
        
            ZGUYPJJFHYFLBV-UHFFFAOYSA-N
        
            AKOS030572810
        
Classifies
                

                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassImidolactams
SubclassNot available
Intermediate Tree NodesNot available
Direct ParentImidolactams
Alternative Parents
Molecular FrameworkAromatic heteromonocyclic compounds
SubstituentsImidolactam - Azole - Isoxazole - Carbamic acid ester - Heteroaromatic compound - Carbonic acid derivative - Oxacycle - Azacycle - Organic oxide - Organopnictogen compound - Organooxygen compound - Organonitrogen compound - Organic oxygen compound - Carbonyl group - Organic nitrogen compound - Hydrocarbon derivative - Aromatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as imidolactams. These are cyclic organooxygen compounds containing the structure RC(=N)N where the central carbon atom and one of the linked nitrogen atoms are part of the same ring( R here is an organyl group). They can also be viewed as analogs of lactams where the oxygen atom is replaced by a nitrogen atom.

Properties

Property NameProperty Value
Molecular Weight198.222
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count3
Complexity213
Monoisotopic Mass198.1
Exact Mass198.1
XLogP2
Formal Charge0
Heavy Atom Count14
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+0.9350
Human Intestinal AbsorptionHIA+1.0000
Caco-2 PermeabilityCaco2+0.5273
P-glycoprotein SubstrateNon-substrate0.8196
P-glycoprotein InhibitorNon-inhibitor0.7248
Non-inhibitor0.6095
Renal Organic Cation TransporterNon-inhibitor0.9608
Distribution
Subcellular localizationMitochondria0.6049
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8304
CYP450 2D6 SubstrateNon-substrate0.8392
CYP450 3A4 SubstrateNon-substrate0.5166
CYP450 1A2 InhibitorInhibitor0.6371
CYP450 2C9 InhibitorNon-inhibitor0.7504
CYP450 2D6 InhibitorNon-inhibitor0.8838
CYP450 2C19 InhibitorNon-inhibitor0.6224
CYP450 3A4 InhibitorNon-inhibitor0.9808
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.7331
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9821
Non-inhibitor0.9439
AMES ToxicityNon AMES toxic0.5248
CarcinogensNon-carcinogens0.7697
Fish ToxicityLow FHMT0.7003
Tetrahymena Pyriformis ToxicityHigh TPT0.6326
Honey Bee ToxicityLow HBT0.5502
BiodegradationNot ready biodegradable0.9764
Acute Oral ToxicityIII0.4809
Carcinogenicity (Three-class)Non-required0.4352

Model Value Unit
Absorption
Aqueous solubility-2.8188LogS
Caco-2 Permeability1.5216LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity3.0039LD50, mol/kg
Fish Toxicity1.1705pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.1700pIGC50, 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