Nitrilacarb

Basic Info

Common NameNitrilacarb(F04014)
2D Structure
Description

Nitrilacarb 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 IDF04014
CAS Number29672-19-3
PubChem CID9570637
FormulaC9H15N3O2
IUPAC Name

[(E)-(4-cyano-2,2-dimethylbutylidene)amino] N-methylcarbamate

InChI Key

FWISWWONCDDGEX-KPKJPENVSA-N

InChI

InChI=1S/C9H15N3O2/c1-9(2,5-4-6-10)7-12-14-8(13)11-3/h7H,4-5H2,1-3H3,(H,11,13)/b12-7+

Canonical SMILES

CC(C)(CCC#N)C=NOC(=O)NC

Isomeric SMILES

CC(C)(CCC#N)/C=N/OC(=O)NC

Synonyms
        
            AI3-27711
        
            Nitrilacarb
        
            UNII-N17QYK0U2Z
        
            N17QYK0U2Z
        
            29672-19-3
        
            Nitrilacarb [ANSI]
        
            Nitrilacarb [ANSI:ISO]
        
            SCHEMBL5933807
        
            DTXSID4042204
        
            CHEBI:82094
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic acids and derivatives
ClassCarboximidic acids and derivatives
SubclassNot available
Intermediate Tree NodesNot available
Direct ParentCarboximidic acids and derivatives
Alternative Parents
Molecular FrameworkAliphatic acyclic compounds
SubstituentsOrganic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Nitrile - Carbonitrile - Carboximidic acid derivative - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Imine - Aliphatic acyclic compound
DescriptionThis compound belongs to the class of organic compounds known as carboximidic acids and derivatives. These are compounds containing a carboximidic group, with the general formula R-C(=NR1)OR2.

Properties

Property NameProperty Value
Molecular Weight197.238
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count5
Complexity263
Monoisotopic Mass197.116
Exact Mass197.116
XLogP0.8
Formal Charge0
Heavy Atom Count14
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

Targets

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
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