Basic Info

Common NamePyrolan(F04027)
2D Structure
Description

Pyrolan 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 IDF04027
CAS Number87-47-8
PubChem CID6888
FormulaC13H15N3O2
IUPAC Name

(5-methyl-2-phenylpyrazol-3-yl) N,N-dimethylcarbamate

InChI Key

GEDIWDLJKRKBFT-UHFFFAOYSA-N

InChI

InChI=1S/C13H15N3O2/c1-10-9-12(18-13(17)15(2)3)16(14-10)11-7-5-4-6-8-11/h4-9H,1-3H3

Canonical SMILES

CC1=NN(C(=C1)OC(=O)N(C)C)C2=CC=CC=C2

Isomeric SMILES

CC1=NN(C(=C1)OC(=O)N(C)C)C2=CC=CC=C2

Synonyms
        
            3-Methyl-1-phenylpyrazol-5-yl dimethylcarbamate
        
            PYROLAN
        
            Pyralan
        
            Geigy G-22008
        
            87-47-8
        
            Caswell No. 574A
        
            OMS 20
        
            ENT 17,588
        
            NSC 404297
        
            3-Methyl-1-phenylpyrazol-5-yl dimethyl carbamate
        
Classifies
                

                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassAzoles
SubclassPyrazoles
Intermediate Tree NodesNot available
Direct ParentPhenylpyrazoles
Alternative Parents
Molecular FrameworkAromatic heteromonocyclic compounds
SubstituentsPhenylpyrazole - Monocyclic benzene moiety - Benzenoid - Carbamic acid ester - Heteroaromatic compound - Carbonic acid derivative - Azacycle - Organic nitrogen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organooxygen compound - Organonitrogen compound - Organic oxygen compound - Carbonyl group - Aromatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as phenylpyrazoles. These are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group.

Properties

Property NameProperty Value
Molecular Weight245.282
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count3
Rotatable Bond Count3
Complexity290
Monoisotopic Mass245.116
Exact Mass245.116
XLogP2.4
Formal Charge0
Heavy Atom Count18
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+0.9885
Human Intestinal AbsorptionHIA+1.0000
Caco-2 PermeabilityCaco2+0.7027
P-glycoprotein SubstrateNon-substrate0.8723
P-glycoprotein InhibitorNon-inhibitor0.6795
Non-inhibitor0.6646
Renal Organic Cation TransporterNon-inhibitor0.9214
Distribution
Subcellular localizationMitochondria0.8442
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7216
CYP450 2D6 SubstrateNon-substrate0.6074
CYP450 3A4 SubstrateSubstrate0.6695
CYP450 1A2 InhibitorInhibitor0.6149
CYP450 2C9 InhibitorNon-inhibitor0.8742
CYP450 2D6 InhibitorNon-inhibitor0.8840
CYP450 2C19 InhibitorNon-inhibitor0.7813
CYP450 3A4 InhibitorNon-inhibitor0.9682
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.6782
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9644
Non-inhibitor0.8147
AMES ToxicityNon AMES toxic0.5000
CarcinogensNon-carcinogens0.8551
Fish ToxicityHigh FHMT0.9967
Tetrahymena Pyriformis ToxicityLow TPT0.5637
Honey Bee ToxicityLow HBT0.7025
BiodegradationNot ready biodegradable0.9176
Acute Oral ToxicityII0.7173
Carcinogenicity (Three-class)Non-required0.5179

Model Value Unit
Absorption
Aqueous solubility-2.1529LogS
Caco-2 Permeability1.3744LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity3.5656LD50, mol/kg
Fish Toxicity0.9877pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.3146pIGC50, 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