Cypendazole

Basic Info

Common NameCypendazole(F03983)
2D Structure
Description

Cypendazole 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 IDF03983
CAS Number28559-00-4
PubChem CID34280
FormulaC16H19N5O3
IUPAC Name

methyl N-[1-(5-cyanopentylcarbamoyl)benzimidazol-2-yl]carbamate

InChI Key

MKZGVGOBXZJKGV-UHFFFAOYSA-N

InChI

InChI=1S/C16H19N5O3/c1-24-16(23)20-14-19-12-8-4-5-9-13(12)21(14)15(22)18-11-7-3-2-6-10-17/h4-5,8-9H,2-3,6-7,11H2,1H3,(H,18,22)(H,19,20,23)

Canonical SMILES

COC(=O)NC1=NC2=CC=CC=C2N1C(=O)NCCCCCC#N

Isomeric SMILES

COC(=O)NC1=NC2=CC=CC=C2N1C(=O)NCCCCCC#N

Synonyms
        
            Cypendazole
        
            Cypendazol
        
            Cypendazole [ISO]
        
            BAY 6233
        
            28559-00-4
        
            UNII-SL67GU815E
        
            BAY 6233a
        
            BAY-DAM 18654
        
            EINECS 249-082-1
        
            DAM 18654
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassBenzimidazoles
SubclassNot available
Intermediate Tree NodesNot available
Direct ParentBenzimidazoles
Alternative Parents
Molecular FrameworkAromatic heteropolycyclic compounds
SubstituentsBenzimidazole - N-substituted imidazole - Benzenoid - Azole - Imidazole - Heteroaromatic compound - Isourea - Propargyl-type 1,3-dipolar organic compound - Azacycle - Nitrile - Carbonitrile - Carboximidic acid derivative - Organic 1,3-dipolar compound - Organooxygen compound - Organonitrogen compound - Hydrocarbon derivative - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Aromatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as benzimidazoles. These are organic compounds containing a benzene ring fused to an imidazole ring (five member ring containing a nitrogen atom, 4 carbon atoms, and two double bonds).

Properties

Property NameProperty Value
Molecular Weight329.36
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count5
Rotatable Bond Count7
Complexity489
Monoisotopic Mass329.149
Exact Mass329.149
XLogP1.6
Formal Charge0
Heavy Atom Count24
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

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