Promacyl

Basic Info

Common NamePromacyl(F04020)
2D Structure
Description

Promacyl 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 IDF04020
CAS Number34264-24-9
PubChem CID36733
FormulaC16H23NO3
IUPAC Name

(3-methyl-5-propan-2-ylphenyl) N-(2-oxopentyl)carbamate

InChI Key

GGRLUNQHANDPSC-UHFFFAOYSA-N

InChI

InChI=1S/C16H23NO3/c1-5-6-14(18)10-17-16(19)20-15-8-12(4)7-13(9-15)11(2)3/h7-9,11H,5-6,10H2,1-4H3,(H,17,19)

Canonical SMILES

CCCC(=O)CNC(=O)OC1=CC(=CC(=C1)C(C)C)C

Isomeric SMILES

CCCC(=O)CNC(=O)OC1=CC(=CC(=C1)C(C)C)C

Synonyms
        
            Butyrylmethyl carbamic acid m-cym-5-yl ester
        
            Promacyl
        
            Promicide
        
            CRC 7320
        
            BRN 2145981
        
            5-Methyl-m-cumenyl butyryl (methyl)carbamate
        
            CARBAMIC ACID, BUTYRYLMETHYL-, m-CYM-5-YL ESTER
        
            m-Cym-5-yl butyrylmethyl carbamate (8CI)
        
            AC1L1WBC
        
            SCHEMBL5933923
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassCumenes
Intermediate Tree NodesNot available
Direct ParentCumenes
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsCumene - Phenylpropane - Phenoxy compound - Toluene - Carbamic acid ester - Ketone - Carbonic acid derivative - Organopnictogen compound - Organic oxygen compound - Organooxygen compound - Organonitrogen compound - Carbonyl group - Organic nitrogen compound - Organic oxide - Hydrocarbon derivative - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as cumenes. These are aromatic compounds containing a prop-2-ylbenzene moiety.

Properties

Property NameProperty Value
Molecular Weight277.364
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count7
Complexity328
Monoisotopic Mass277.168
Exact Mass277.168
XLogP3.7
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+0.9627
Human Intestinal AbsorptionHIA+1.0000
Caco-2 PermeabilityCaco2+0.6075
P-glycoprotein SubstrateNon-substrate0.5671
P-glycoprotein InhibitorNon-inhibitor0.6270
Non-inhibitor0.6459
Renal Organic Cation TransporterNon-inhibitor0.9059
Distribution
Subcellular localizationMitochondria0.8592
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7875
CYP450 2D6 SubstrateNon-substrate0.6973
CYP450 3A4 SubstrateSubstrate0.5861
CYP450 1A2 InhibitorInhibitor0.5285
CYP450 2C9 InhibitorNon-inhibitor0.6341
CYP450 2D6 InhibitorNon-inhibitor0.7969
CYP450 2C19 InhibitorNon-inhibitor0.5476
CYP450 3A4 InhibitorNon-inhibitor0.7266
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.6593
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.8546
Non-inhibitor0.7751
AMES ToxicityNon AMES toxic0.7322
CarcinogensNon-carcinogens0.8399
Fish ToxicityHigh FHMT0.9348
Tetrahymena Pyriformis ToxicityHigh TPT0.9703
Honey Bee ToxicityHigh HBT0.6421
BiodegradationNot ready biodegradable0.8977
Acute Oral ToxicityIII0.6067
Carcinogenicity (Three-class)Non-required0.5748
Model Value Unit
Absorption
Aqueous solubility-4.0080LogS
Caco-2 Permeability1.2793LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.4488LD50, mol/kg
Fish Toxicity1.0118pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.3390pIGC50, 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