Butocarboxim

Basic Info

Common NameButocarboxim(F03969)
2D Structure
Description

Butocarboxim 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 IDF03969
CAS Number34681-10-2
PubChem CID5368008
FormulaC7H14N2O2S
IUPAC Name

[(Z)-3-methylsulfanylbutan-2-ylideneamino] N-methylcarbamate

InChI Key

SFNPDDSJBGRXLW-UITAMQMPSA-N

InChI

InChI=1S/C7H14N2O2S/c1-5(6(2)12-4)9-11-7(10)8-3/h6H,1-4H3,(H,8,10)/b9-5-

Canonical SMILES

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

Isomeric SMILES

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

Synonyms
        
            Butocarboxime [ISO-French]
        
            Butocarboxime
        
            Afiline
        
            BUTOCARBOXIM
        
            3-(Methylthio)-2-butanone O-(methylcarbamoyl)oxime
        
            Drawin 755
        
            Butocarboxim [German]
        
            Butocarboxim [BSI:ISO]
        
            3-(Methylthio)-2-butanone O-((methylamino)carbonyl)oxime
        
            N-(methylcarbamoyloxy)-3-(methylsulfanyl)butan-2-imine
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic nitrogen compounds
ClassOrganonitrogen compounds
SubclassOxime carbamates
Intermediate Tree NodesNot available
Direct ParentOxime carbamates
Alternative Parents
Molecular FrameworkAliphatic acyclic compounds
SubstituentsOxime carbamate - Ketoxime - Carbonic acid derivative - Dialkylthioether - Sulfenyl compound - Thioether - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organosulfur compound - Organooxygen compound - Carbonyl group - Aliphatic acyclic compound
DescriptionThis compound belongs to the class of organic compounds known as oxime carbamates. These are oxime ether derivatives with the general formula CC(R)=NOC(=O)N(R')R\", where R-R\" = H or organyl.

Properties

Property NameProperty Value
Molecular Weight190.261
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count4
Complexity182
Monoisotopic Mass190.078
Exact Mass190.078
XLogP1.2
Formal Charge0
Heavy Atom Count12
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9468
Human Intestinal AbsorptionHIA+0.9965
Caco-2 PermeabilityCaco2-0.5208
P-glycoprotein SubstrateNon-substrate0.8583
P-glycoprotein InhibitorNon-inhibitor0.8895
Non-inhibitor0.9169
Renal Organic Cation TransporterNon-inhibitor0.9476
Distribution
Subcellular localizationMitochondria0.6657
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7525
CYP450 2D6 SubstrateNon-substrate0.8982
CYP450 3A4 SubstrateNon-substrate0.6418
CYP450 1A2 InhibitorNon-inhibitor0.5750
CYP450 2C9 InhibitorNon-inhibitor0.7738
CYP450 2D6 InhibitorNon-inhibitor0.9049
CYP450 2C19 InhibitorNon-inhibitor0.6999
CYP450 3A4 InhibitorNon-inhibitor0.9602
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8876
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9893
Non-inhibitor0.9724
AMES ToxicityNon AMES toxic0.7122
CarcinogensCarcinogens 0.5209
Fish ToxicityHigh FHMT0.6484
Tetrahymena Pyriformis ToxicityLow TPT0.5811
Honey Bee ToxicityHigh HBT0.8825
BiodegradationNot ready biodegradable0.9942
Acute Oral ToxicityII0.7752
Carcinogenicity (Three-class)Non-required0.6511
Model Value Unit
Absorption
Aqueous solubility-0.4069LogS
Caco-2 Permeability1.3878LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity3.7546LD50, mol/kg
Fish Toxicity0.4840pLC50, mg/L
Tetrahymena Pyriformis Toxicity-0.2390pIGC50, ug/L

Targets

Target Details

Acetylcholinesterase

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
Target Details

Cholinesterase

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