CARBAMATES

CARBAMATES Struktur
CAS-Nr.
Englisch Name:
CARBAMATES
Synonyma:
CARBAMATES
CBNumber:
CB01091908
Summenformel:
Molgewicht:
0
MOL-Datei:
Mol file

CARBAMATES Eigenschaften

Sicherheit

CARBAMATES Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung

The first carbamate esters to exhibit insecticidal activity were derivatives of dithiocarbamic acid. A few of these were contact poisons to soft-bodied insects (aphids), whereas others, including thiram, demonstrated antifeedant properties. In subsequent studies with physostigmine and related carbamate compounds, the charge of amine salts and quaternary structures was shown to prevent their penetration through the waxy cuticle and into the fatty nervous system of insects. Several substituted-phenyl monomethylcarbamates were shown to be effective contact toxins for aphids, flies, and thrips. Still later, the oxime carbamates were discovered and shown to be effective contact and systemic insecticides, nematocides and/or miticides.

Pharmakologie

Carbamate anticholinesterase agents are carbamic acid esters that are hydrolyzed by AChE in a manner similar to that of ACh. Carbamates have this general structure:
The clinically useful carbamates generally contain a tertiary or quaternary amine group that can bind noncovalently to the anionic site of the enzyme.The inhibition of AChE by neostigmine (Prostigmin) illustrates the general mechanism. The quaternary ammonium group of neostigmine binds electrostatically to the anionic site of the enzyme, thereby orienting the drug. The carbamates generally inhibit pseudo-ChE as well as true AChE, and their suicidal degradation by cholinesterases contributes importantly to terminating their duration of effect. Physostigmine (also called eserine) (Antilirium) is a tertiary amine that can inhibit AChE in the CNS, and it can be used in life-threatening cases to treat antimuscarinic poisoning.
Pyridostigmine (Mestinon) is a quaternary ammonium carbamate. Neostigmine and pyridostigmine also have direct agonist activity at nicotinic receptors on skeletal muscle. Rivastigmine (Exelon) is a carbamate cholinesterase inhibitor with good penetration into the brain.

Stoffwechsel

The carbamates are generally broken down by hydrolysis into the parent alcohol/phenol and a substituted carbamic acid. The substituted carbamic acid formed is unstable and decomposes with loss of carbon dioxide to give an amine derivative.
Numerous microorganisms in vitro have the ability to hydrolyze promacyl either at the amide bond to form promecarb or at the ester bond to form isothymol(16). McDougall and Makin (17) reported that microbial degradation accounts for seasonal declines observed in promacyl concentrations in cattle plunge dips and that stabilization of promacyl can be achieved by adjusting the dip wash pH to <4.5.

CARBAMATES Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


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