Basic Info

Common NameFormparanate(F03999)
2D Structure
Description

Formparanate 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 IDF03999
CAS Number17702-57-7
PubChem CID37148
FormulaC12H18ClN3O2
IUPAC Name

dimethyl-[[2-methyl-4-(methylcarbamoyloxy)phenyl]iminomethyl]azanium;chloride

InChI Key

SDIUYIZASVDZKT-UHFFFAOYSA-N

InChI

InChI=1S/C12H17N3O2.ClH/c1-9-7-10(17-12(16)13-2)5-6-11(9)14-8-15(3)4;/h5-8H,1-4H3,(H,13,16);1H

Canonical SMILES

CC1=C(C=CC(=C1)OC(=O)NC)N=C[NH+](C)C.[Cl-]

Isomeric SMILES

CC1=C(C=CC(=C1)OC(=O)NC)N=C[NH+](C)C.[Cl-]

Synonyms
        
            Carbamic acid, methyl-, 4-(((dimethylamino)methylene)amino)-m-tolyl ester, hydrochloride
        
            dimethyl-[[2-methyl-4-(methylcarbamoyloxy)phenyl]iminomethyl]azanium chloride
        
            Formparanate hydrochloride [ISO]
        
            UC 34096
        
            Carbamic acid, methyl-, ester with N'-(4-hydroxy-o-tolyl)-N,N-dimethylformamidine, HCl
        
            Methanimidamide, N,N-dimethyl-N'-(2-methyl-4-(((methylamino)carbonyl)oxy)phenyl)-, HCl
        
            Methylcarbamic acid 4-(((dimethylamino)methylene)amino)-m-tolyl ester hydrochloride
        
            N,N-Dimethyl-N'-(2-methyl-4-(((methylamino)carbonyl)oxy)phenyl)methanimidamide hydrochloride
        
            AC1L1X4R
        
            LS-50133
        
Classifies
                

                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Properties

Property NameProperty Value
Molecular Weight271.745
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count4
Complexity279
Monoisotopic Mass271.109
Exact Mass271.109
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 Count2

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