Basic Info

Common NameKarbutilate(F04004)
2D Structure
Description

Karbutilate 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 IDF04004
CAS Number4849-32-5
PubChem CID312440
FormulaC14H21N3O3
IUPAC Name

[3-(dimethylcarbamoylamino)phenyl] N-tert-butylcarbamate

InChI Key

OWNAXTAAAQTBSP-UHFFFAOYSA-N

InChI

InChI=1S/C14H21N3O3/c1-14(2,3)16-13(19)20-11-8-6-7-10(9-11)15-12(18)17(4)5/h6-9H,1-5H3,(H,15,18)(H,16,19)

Canonical SMILES

CC(C)(C)NC(=O)OC1=CC=CC(=C1)NC(=O)N(C)C

Isomeric SMILES

CC(C)(C)NC(=O)OC1=CC=CC(=C1)NC(=O)N(C)C

Synonyms
        
            3-(3,3-Dimethylureido)phenyl tert-butylcarbamate
        
            Karbutilate
        
            Tandex
        
            Carbutilate
        
            4849-32-5
        
            Karbutylate
        
            FMC 11092
        
            NIA 11092
        
            UNII-49A0A2590D
        
            m-(3,3-Dimethylureido)phenyl tert-butylcarbamate
        
Classifies
                

                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassN-phenylureas
Intermediate Tree NodesNot available
Direct ParentN-phenylureas
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsN-phenylurea - Phenoxy compound - Carbamic acid ester - Urea - Carbonic acid derivative - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Carbonyl group - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as n-phenylureas. These are compounds containing a N-phenylurea moiety, which is structurally characterized by a phenyl group linked to one nitrogen atom of a urea group.

Properties

Property NameProperty Value
Molecular Weight279.34
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count3
Rotatable Bond Count4
Complexity350
Monoisotopic Mass279.158
Exact Mass279.158
XLogP1.7
Formal Charge0
Heavy Atom Count20
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+0.7959
Human Intestinal AbsorptionHIA+0.9523
Caco-2 PermeabilityCaco2+0.5076
P-glycoprotein SubstrateNon-substrate0.6500
P-glycoprotein InhibitorNon-inhibitor0.8585
Non-inhibitor0.8821
Renal Organic Cation TransporterNon-inhibitor0.9428
Distribution
Subcellular localizationMitochondria0.7074
Metabolism
CYP450 2C9 SubstrateNon-substrate0.6957
CYP450 2D6 SubstrateNon-substrate0.7711
CYP450 3A4 SubstrateSubstrate0.5317
CYP450 1A2 InhibitorNon-inhibitor0.7631
CYP450 2C9 InhibitorNon-inhibitor0.7379
CYP450 2D6 InhibitorNon-inhibitor0.9109
CYP450 2C19 InhibitorNon-inhibitor0.7111
CYP450 3A4 InhibitorNon-inhibitor0.8845
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8061
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9408
Non-inhibitor0.8607
AMES ToxicityNon AMES toxic0.5943
CarcinogensNon-carcinogens0.6282
Fish ToxicityHigh FHMT0.8803
Tetrahymena Pyriformis ToxicityHigh TPT0.7623
Honey Bee ToxicityLow HBT0.5906
BiodegradationNot ready biodegradable0.9917
Acute Oral ToxicityIII0.7867
Carcinogenicity (Three-class)Non-required0.6142

Model Value Unit
Absorption
Aqueous solubility-2.9925LogS
Caco-2 Permeability1.1434LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.0005LD50, mol/kg
Fish Toxicity0.9463pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.2887pIGC50, 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