Basic Info

Common NameButoxycarboxim(F03970)
2D Structure
Description

Butoxycarboxim 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 IDF03970
CAS Number34681-23-7
PubChem CID9571009
FormulaC7H14N2O4S
IUPAC Name

[(E)-3-methylsulfonylbutan-2-ylideneamino] N-methylcarbamate

InChI Key

CTJBHIROCMPUKL-WEVVVXLNSA-N

InChI

InChI=1S/C7H14N2O4S/c1-5(6(2)14(4,11)12)9-13-7(10)8-3/h6H,1-4H3,(H,8,10)/b9-5+

Canonical SMILES

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

Isomeric SMILES

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

Synonyms
        
            3-(Methylsulfonyl)-2-butanone O-(methylcarbamoyl)oxime
        
            Butoxycarboxim
        
            Butoxycarboxime
        
            3-Mesylbutanone O-methylcarbamoyloxime
        
            Plant pin
        
            34681-23-7
        
            Caswell No. 120A
        
            3-(Methylsulfonyl)-2-butanone O-((methylamino)carbonyl)oxime
        
            Butoxicarboxim [German]
        
            Butoxycarboxim [BSI:ISO]
        
Classifies
                

                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganosulfur compounds
ClassSulfonyls
SubclassSulfones
Intermediate Tree NodesNot available
Direct ParentSulfones
Alternative Parents
Molecular FrameworkAliphatic acyclic compounds
SubstituentsSulfone - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Carboximidic acid derivative - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Imine - Aliphatic acyclic compound
DescriptionThis compound belongs to the class of organic compounds known as sulfones. These are compounds containing a sulfonyl group( which as the general structure RS(=O)2R' (R,R' =alkyl, aryl)) attached to two carbon atoms.

Properties

Property NameProperty Value
Molecular Weight222.259
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count5
Rotatable Bond Count4
Complexity328
Monoisotopic Mass222.067
Exact Mass222.067
XLogP-0.1
Formal Charge0
Heavy Atom Count14
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+0.8024
Human Intestinal AbsorptionHIA+0.9448
Caco-2 PermeabilityCaco2-0.5766
P-glycoprotein SubstrateNon-substrate0.8606
P-glycoprotein InhibitorNon-inhibitor0.9013
Non-inhibitor0.8255
Renal Organic Cation TransporterNon-inhibitor0.9594
Distribution
Subcellular localizationMitochondria0.6168
Metabolism
CYP450 2C9 SubstrateNon-substrate0.6300
CYP450 2D6 SubstrateNon-substrate0.8304
CYP450 3A4 SubstrateNon-substrate0.6229
CYP450 1A2 InhibitorNon-inhibitor0.7760
CYP450 2C9 InhibitorNon-inhibitor0.7661
CYP450 2D6 InhibitorNon-inhibitor0.9004
CYP450 2C19 InhibitorNon-inhibitor0.5942
CYP450 3A4 InhibitorNon-inhibitor0.9698
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9724
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9931
Non-inhibitor0.9440
AMES ToxicityNon AMES toxic0.5000
CarcinogensCarcinogens 0.5994
Fish ToxicityHigh FHMT0.8491
Tetrahymena Pyriformis ToxicityLow TPT0.5594
Honey Bee ToxicityHigh HBT0.7370
BiodegradationNot ready biodegradable0.9896
Acute Oral ToxicityII0.7659
Carcinogenicity (Three-class)Non-required0.6312

Model Value Unit
Absorption
Aqueous solubility-1.6096LogS
Caco-2 Permeability0.6410LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.9804LD50, mol/kg
Fish Toxicity1.0322pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.0282pIGC50, 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