Allyxycarb

Basic Info

Common NameAllyxycarb(F03955)
2D Structure
Description

Allyxycarb 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 IDF03955
CAS Number6392-46-7
PubChem CID22890
FormulaC16H22N2O2
IUPAC Name

[4-[bis(prop-2-enyl)amino]-3,5-dimethylphenyl] N-methylcarbamate

InChI Key

FBEHFRAORPEGFH-UHFFFAOYSA-N

InChI

InChI=1S/C16H22N2O2/c1-6-8-18(9-7-2)15-12(3)10-14(11-13(15)4)20-16(19)17-5/h6-7,10-11H,1-2,8-9H2,3-5H3,(H,17,19)

Canonical SMILES

CC1=CC(=CC(=C1N(CC=C)CC=C)C)OC(=O)NC

Isomeric SMILES

CC1=CC(=CC(=C1N(CC=C)CC=C)C)OC(=O)NC

Synonyms
        
            Allyxycarb [BSI:ISO]
        
            Allyxycarb
        
            APC (pesticide)
        
            6392-46-7
        
            Hydrol (insecticide)
        
            Caswell No. 283A
        
            UNII-66S9S03B4N
        
            EINECS 229-002-1
        
            BAY 50282
        
            EPA Pesticide Chemical Code 283600
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassPhenyl methylcarbamates
Intermediate Tree NodesNot available
Direct ParentPhenyl methylcarbamates
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsPhenyl methylcarbamate - Phenoxy compound - Tertiary aliphatic/aromatic amine - M-xylene - Xylene - Dialkylarylamine - Aniline or substituted anilines - Carbamic acid ester - Carbonic acid derivative - Tertiary amine - Amine - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Carbonyl group - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as phenyl methylcarbamates. These are aromatic compounds containing a methylcarbamic acid esterified with a phenyl group.

Properties

Property NameProperty Value
Molecular Weight274.364
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count7
Complexity321
Monoisotopic Mass274.168
Exact Mass274.168
XLogP3.8
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+0.9849
Human Intestinal AbsorptionHIA+0.9678
Caco-2 PermeabilityCaco2+0.6593
P-glycoprotein SubstrateNon-substrate0.6635
P-glycoprotein InhibitorNon-inhibitor0.7591
Inhibitor0.5680
Renal Organic Cation TransporterNon-inhibitor0.7980
Distribution
Subcellular localizationMitochondria0.7401
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7887
CYP450 2D6 SubstrateNon-substrate0.5822
CYP450 3A4 SubstrateSubstrate0.6246
CYP450 1A2 InhibitorNon-inhibitor0.6005
CYP450 2C9 InhibitorNon-inhibitor0.8675
CYP450 2D6 InhibitorNon-inhibitor0.7492
CYP450 2C19 InhibitorNon-inhibitor0.6374
CYP450 3A4 InhibitorInhibitor0.5293
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.5000
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.7308
Non-inhibitor0.7357
AMES ToxicityAMES toxic0.5418
CarcinogensNon-carcinogens0.6922
Fish ToxicityHigh FHMT0.9724
Tetrahymena Pyriformis ToxicityHigh TPT0.9214
Honey Bee ToxicityLow HBT0.5220
BiodegradationNot ready biodegradable0.9960
Acute Oral ToxicityII0.7278
Carcinogenicity (Three-class)Non-required0.5902
Model Value Unit
Absorption
Aqueous solubility-2.8006LogS
Caco-2 Permeability1.4528LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity3.5202LD50, mol/kg
Fish Toxicity0.8007pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.3899pIGC50, 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