Isolan

Basic Info

Common NameIsolan(F04002)
2D Structure
Description

Isolan 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 IDF04002
CAS Number119-38-0
PubChem CID8393
FormulaC10H17N3O2
IUPAC Name

(5-methyl-2-propan-2-ylpyrazol-3-yl) N,N-dimethylcarbamate

InChI Key

RNNBHZYEKNHLKT-UHFFFAOYSA-N

InChI

InChI=1S/C10H17N3O2/c1-7(2)13-9(6-8(3)11-13)15-10(14)12(4)5/h6-7H,1-5H3

Canonical SMILES

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

Isomeric SMILES

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

Synonyms
        
            Saolan
        
            Isopropylmethylpyrazolyl dimethylcarbamate
        
            ISOLAN
        
            Isolane
        
            Isolan (pesticide)
        
            Isolane [French]
        
            Geigy G-23611
        
            Caswell No. 511D
        
            OMS 62
        
            ENT 19,060
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassAzoles
SubclassPyrazoles
Intermediate Tree NodesNot available
Direct ParentPyrazoles
Alternative Parents
Molecular FrameworkAromatic heteromonocyclic compounds
SubstituentsHeteroaromatic compound - Carbamic acid ester - Pyrazole - Carbonic acid derivative - Azacycle - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Carbonyl group - Aromatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as pyrazoles. These are compounds containing a pyrazole ring, which is a five-member aromatic ring with two nitrogen atoms (at positions 1 and 2) and three carbon atoms.

Properties

Property NameProperty Value
Molecular Weight211.265
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count3
Rotatable Bond Count3
Complexity231
Monoisotopic Mass211.132
Exact Mass211.132
XLogP1.4
Formal Charge0
Heavy Atom Count15
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+0.9936
Human Intestinal AbsorptionHIA+1.0000
Caco-2 PermeabilityCaco2+0.6271
P-glycoprotein SubstrateNon-substrate0.8474
P-glycoprotein InhibitorNon-inhibitor0.6970
Non-inhibitor0.9100
Renal Organic Cation TransporterNon-inhibitor0.9051
Distribution
Subcellular localizationMitochondria0.7937
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7569
CYP450 2D6 SubstrateNon-substrate0.6823
CYP450 3A4 SubstrateSubstrate0.6106
CYP450 1A2 InhibitorNon-inhibitor0.5925
CYP450 2C9 InhibitorNon-inhibitor0.9074
CYP450 2D6 InhibitorNon-inhibitor0.8883
CYP450 2C19 InhibitorNon-inhibitor0.8326
CYP450 3A4 InhibitorNon-inhibitor0.9837
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9094
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9637
Non-inhibitor0.8859
AMES ToxicityNon AMES toxic0.5798
CarcinogensNon-carcinogens0.8733
Fish ToxicityHigh FHMT0.9618
Tetrahymena Pyriformis ToxicityLow TPT0.7649
Honey Bee ToxicityLow HBT0.5702
BiodegradationNot ready biodegradable0.5600
Acute Oral ToxicityI0.7781
Carcinogenicity (Three-class)Non-required0.5522
Model Value Unit
Absorption
Aqueous solubility-1.4912LogS
Caco-2 Permeability1.1866LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity4.2601LD50, mol/kg
Fish Toxicity1.2184pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.0590pIGC50, 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