Thiocyclam

ChEBI: An organosulfur heterocyclic compound that is 1,2,3-trithiane in which one of the hydrogens at position 5 has been replaced by a dimethylamino group.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.

Thiocyclam is an organosulfur heterocyclic compound that is 1,2,3-trithiane in which one of the hydrogens at position 5 has been replaced by a dimethylamino group.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 as 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. It has a role as an agrochemical and a nicotinic acetylcholine receptor agonist. It is a nereistoxin analogue insecticide and an organosulfur heterocyclic compound. It is a conjugate base of a thiocyclam(1+). It derives from a hydride of a 1,2,3-trithiane.

Preparation method 1: Preparation of 2-N,N-dimethylamino-1-thiosulfonate-3-thiosulfonate sodium propane Take 7.7g of N,N-dimethylamino-2,3-dichlorolactam Add 20mL of water and 20mL of methanol, and react at 60℃ for 2h. Distill methanol and part of the water. Filter off the precipitated solid. After the mother liquor is placed, a white solid precipitates out. Repeated treatment of the mother liquor. Income 15.4g thiosulfonate, the crude yield is 98%, recrystallized to obtain colorless crystals, mp142～143℃(decomposition). Preparation of 5-N,N-dimethylamino-1,2,3-trithiohexanol oxalate Take 9.99g of sulfonate, add 100mL pH=8 buffer solution (0.5mol sodium dihydrogen phosphate and 0.5mol Potassium dihydrogen phosphate), 48g sodium chloride, 18mL chloroform. Stir and cool to -4°C, add dropwise a solution of 7.6g of sodium sulfide in 30mL of water, and react for 30min. The chloroform layer was separated and neutralized to pH 4 with 2.7 g of oxalic acid in alcohol solution. After precipitation and drying, 7.8 g of product was obtained, with a yield of 95%. After recrystallization, the melting point is 131～132℃ (decomposition). The insecticidal ring can also be prepared by the reaction of Dimehypo with alkali sulfide and then with acid. Preparation method 2: The Swiss Sandoz company reported that 3-N,N-dimethylamino-1,2-dichloropropane was prepared by amination and chlorination from propylene chloride as the starting material, and then mixed with sodium thiobenzene sulfonate The reaction produces 1,3-bis(phenylthiosulfonyl)-2-dimethylaminopropane, which is then cyclized with sodium thiosulfate to form a salt with oxalic acid. Preparation method 3 Japan's Takeda Chemical Industry Co., Ltd. reported a new simple method in 1975, that is, the direct reaction of 3-N,N-dimethylamino-1,2-dichloropropane with polysulfide (sodium). Preparation method 4: Sandoz Company reported that starting from 3-N,N-dimethylamino-1,2-dichloropropane, after 1,3-bis(benzylthio)-2-dimethylaminopropane or 1,3-bis (Thioacetyl)-2-dimethylaminopropane is used to produce 1,3-dimercapto-2-dimethylaminopropane, which is then reacted with sulfur dichloride to produce an insecticidal ring, and then reacts with oxalic acid to produce insecticide Cyclooxalate.

Nereid toxin insecticides have contact killing, stomach poisoning, certain systemic conduction effects, and egg killing properties. This product has a slow toxic effect on pests and a short residual effect period, and has a good control effect on lepidoptera and coleoptera pests. Mainly used for rice pests, the general dosage is 5.3～7.5g active ingredient/100m2, and the control effect is more than 90%. For example, to control rice stem borer and rice borer, use 50% soluble powder 10.5～12g/100m2, splash or spray on water. For the prevention and control of rice leaf roller borer and rice bract, the same amount of chemicals can also be used for splashing. Can be mixed with fast-acting pesticides. Use with caution in silkworm areas.

Molecular Weight:181.4
XLogP3:1.2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:181.00536288
Monoisotopic Mass:181.00536288
Topological Polar Surface Area:79.1
Heavy Atom Count:9
Complexity:80.3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes