Chemical Properties
The pure oxalate salt appears as white crystals. Its mp is 125-128°C (decomposition), and its vapor pressure is 5.333×10-4 Pa (20°C). Its solubility at 23°C is 92 g/L in dimethyl sulfoxide, 17 g/L in methanol, 1.9 g/L in ethanol, 1.2 g/L in acetonitrile, 545 mg/L in acetone, 225 mg/L in ethyl acetate, 46 mg/L in chloroform, <10 mg/L in toluene, and 84 g/L in water. It is insoluble in ether, xylene, and kerosene. It is stable under acidic or light-protected conditions. The half-life of a 40 mg/L aqueous solution at room temperature and pH 3-5 is 41 days, and at pH 7-9 it is 11 days. A 5 mg/L aqueous solution decomposes 30% in 1 hour under sunlight.
Uses
Thiocyclam is a pro-insecticide of the natural
toxin nereistoxin and is rapidly converted into the
latter in biological media. It has limited systemic activity
with stomach and contact action. It causes paralysis
by ganglionic blocking action on the insect central nervous
system. It is used as the hydrogen oxalate salt. This is converted
to the active nereistoxin, and its oxide in soils and
plants and these are ultimately broken down into smaller
molecules.
Definition
ChEBI: An organosulfur heterocyclic compound that is 1,2,3-trithiane in which one of the hydrogens at position 5 has been replaced by a dimethylamino group. A nicotinic acetylcholine receptor agonist, it was used (particularly as its hydrogen oxalate salt, known
s thyocyclam oxalate) as a broad-spectrum insecticide, but it is also toxic to bees, fish and other aquatic organisms. It is not approved for use within the European Union.
Production Methods
Thiocyclam is commercially synthesised through a multi-step process involving the formation of a trithiane ring system and N,N-dimethylation. The production begins with the cyclization of 1,3-propanedithiol and formaldehyde to form a 1,2,3-trithiane ring, which serves as the core structure. This intermediate is then subjected to N-alkylation using dimethylamine or dimethyl sulphate to introduce the N,N-dimethylamino group at the 5-position of the ring. The reaction is typically carried out under controlled temperature and pH conditions to ensure selectivity and minimise byproducts.
Mechanism of action
A nereistoxin analogue insecticide. Selective, stomach acting with some contact action. Nicotinic acetylcholine receptor (nAChR) channel blocker.
Pesticide Type
Insecticide
