Thiocarboxime

Basic Info

Common NameThiocarboxime(F04033)
2D Structure
Description

Thiocarboxime 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 IDF04033
CAS Number25171-63-5
PubChem CID34476
FormulaC7H11N3O2S
IUPAC Name

2-cyanoethyl N-(methylcarbamoyloxy)ethanimidothioate

InChI Key

IWRFWZPCCDGEFJ-UHFFFAOYSA-N

InChI

InChI=1S/C7H11N3O2S/c1-6(13-5-3-4-8)10-12-7(11)9-2/h3,5H2,1-2H3,(H,9,11)

Canonical SMILES

CC(=NOC(=O)NC)SCCC#N

Isomeric SMILES

CC(=NOC(=O)NC)SCCC#N

Synonyms
        
            2-cyanoethyl N-(methylcarbamoyloxy)ethanimidothioate
        
            Thiocarboxime [ISO]
        
            Shell 17250
        
            Shell SD 17250
        
            SD 17250W
        
            WL 21959
        
            AI3-27613
        
            AC1L1RMX
        
            3-Thiapentan-2-one, 5-cyano-, O-(methylcarbamoyl)oxime
        
            S-2-Cyanoethyl-N-((methylcarbamoyl)oxy)thio(1,2-)-acetamidate
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic acids and derivatives
ClassOrganic carbonic acids and derivatives
SubclassNot available
Intermediate Tree NodesNot available
Direct ParentOrganic carbonic acids and derivatives
Alternative Parents
Molecular FrameworkAliphatic acyclic compounds
SubstituentsCarbonic acid derivative - Sulfenyl compound - Nitrile - Carbonitrile - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Carbonyl group - Aliphatic acyclic compound
DescriptionThis compound belongs to the class of organic compounds known as organic carbonic acids and derivatives. These are compounds comprising the organic carbonic acid or a derivative thereof.

Properties

Property NameProperty Value
Molecular Weight201.244
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count5
Rotatable Bond Count5
Complexity243
Monoisotopic Mass201.057
Exact Mass201.057
XLogP0.3
Formal Charge0
Heavy Atom Count13
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count1
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