58842-20-9

Usage

Uses

Used in Pest Control Industry:
(2E)-2-(nitromethylidene)-1,3-thiazinane is used as an active ingredient in fly strips for the control of houseflies (Musca domestica). The strips are effective when placed in or around residential areas, animal housing, recycling facilities, or other locations where houseflies are a nuisance. However, the manufacturer does not currently support residential uses.
Used in Chemical Synthesis:
(2E)-2-(nitromethylidene)-1,3-thiazinane is also used as a useful building block and insecticide in the chemical synthesis industry. Its unique properties as a partial agonist and open channel blocker make it a valuable compound for the development of new insecticides and other related products.

Environmental Fate

Nithiazine is extremely unstable in sunlight due to the nitromethylene chromophore. This group absorbs strongly in water at 365 nm with an extinction coefficient about 40 000M-1 cm-1. Direct irradiation results in a loss of the insecticidal activity and formation of a mixture of more than 40 degradation products. The major products of nithiazine photoreduction and dimerization from irradiation at 360 nm in water are nitrile, nitroso, and oxim derivatives, and dimers. Consequently, nithiazine half-time on foliage is only about 30min. Low photostability is the primary reason that nithiazine is not used as an insecticide for field and other environmental applications. Nithiazine stability in aqueous environments is affected by pH. Its half-time is greater than 3months at pH 7, while it is only 3 h at pH 1.1.

Toxicity evaluation

Nithiazine is an agonist acting at the neural nicotinic acetylcholine receptor – Na+/K+ ionophore in mammals and insects. The nicotinic acetylcholine receptors regulate the flow of Na+ and K+ through the channels in the neural postsynaptic membranes. Opening and closing of the channels by acetylcholine maintains the dynamic ratio of the intracellular to extracellular concentrations of Na+ and K+ needed for the initiation of the signal in the postsynaptic neuron. The structural differences between insect and mammalian receptors determine the high selectivity of nithiazine toxicity to insects.

InChI:InChI=1/C5H8N2O2S/c8-7(9)4-5-6-2-1-3-10-5/h4,6H,1-3H2/b5-4+

Upstream product

• 462-47-5 mercapto-3 propylamine 
• 13623-94-4 1,1-di(methylsulfanyl)-2-nitroethylene 

Downstream Products

• 1422006-99-2 6-amino-9-nitro-8-phenyl-2,3,4,8-tetrahydropyrido[2,1-b][1, 3]thiazine-7-carbonitrile 
• 1422007-00-8 6-amino-9-nitro-8-(p-tolyl)-2,3,4,8-tetrahydropyrido[2,1-b][1, 3]thiazine-7-carbonitrile 
• 1422007-01-9 6-amino-8-(4-methoxyphenyl)-9-nitro-2,3,4,8-tetrahydropyrido[2,1-b][1,3]thiazine-7-carbonitrile 
• 1422007-02-0 6-amino-9-nitro-8-(4-nitrophenyl)-2,3,4,8-tetrahydropyrido[2,1-b][1,3]thiazine-7-carbonitrile 
• 1422007-03-1 6-amino-8-(4-chlorophenyl)-9-nitro-2,3,4,8-tetrahydropyrido[2,1-b][1,3]thiazine-7-carbonitrile 
• 1422007-04-2 ethyl 6-amino-9-nitro-8-phenyl-2,3,4,8-tetrahydropyrido[2,1-b][1,3]thiazine-7-carboxylate 
• 1422007-05-3 ethyl 6-amino-9-nitro-8-(p-tolyl)-2,3,4,8-tetrahydropyrido[2,1-b][1,3]thiazine-7-carboxylate 
• 1400278-05-8 ethyl 6-amino-8-(4-methoxyphenyl)-9-nitro-2,3,4,8-tetrahydropyrido[2,1-b][1,3]thiazine-7-carboxylate 
• 1422007-06-4 ethyl 6-amino-9-nitro-8-(4-nitrophenyl)-2,3,4,8-tetrahydropyrido[2,1-b][1,3]thiazine-7-carboxylate 
• 1346557-79-6 ethyl 6-amino-8-(4-chlorophenyl)-9-nitro-2,3,4,8-tetrahydropyrido[2,1-b][1,3]thiazine-7-carboxylate 

Relevant academic research and scientific papers

The structure modification of seven-membered aza-brigded neonicotinoids in order to investigate their impact on honey bees

In order to explore the relationship between the structure and the toxicity to honey bees of seven-membered aza-bridged neonicotinoids, 16 novel seven-membered aza-bridged neonicotinoid analogues are synthesized by replacing the pyridine ring, and changing the substituents on the pyridine ring, the electron-withdrawing group NO2 and the imidazole ring of our previously developed aza-bridged neonicotinoid 1-[(6-chloropyridin-3-yl)methyl)]-10-(2,5-dimethylphenyl)-9-nitro-2,3,5,6,7,8-hexahydro-1H-5,8-epiminoimidazo azepine (C-29). The insecticidal bioactivities against cowpea aphid (Aphis craccivora) and the bee toxicities of these compounds are tested. Some of the title compounds present good insecticidal activities against cowpea aphid. The results also show that some of the title compounds exhibit lower bee toxicity than that of C-29 and imidacloprid. This suggests that changing the substituents on the neonicotinoids can influence the toxicity toward honey bees of these analogues.

Synthesis, biological activity and crystal structure of ethyl 6-amino-8-(4-methoxy phenyl)-9-nitro-2,3,4,8-tetrahydropyrido[2,1b][1,3] thiazine-7-carboxylate

The compound ethyl 6-amino-8-(4-methoxy phenyl)-9-nitro-2,3,4,8- tetrahydropyrido[2,1b][1,3]thiazine-7-carboxylate (C14H 22N4O4S2) has been synthesized by multicomponent reactions, and characterized by 1H NMR, IR, and X-ray diffraction. The crystal structure analysis shows that the thiazinane ring displays a half-chair conformation. The benzene ring is almost vertical to the tetrahydro-pyridine ring. Intramolecular H-bonding of N- H···O type exists and completes an S (6) ring. In the crystal, the molecules are connected into a 3D network by a N- H···O and C-H···O intermolecular hydrogen bond. The bioassay indicates that the compound shows moderate insecticidal activity against Aphis craccivora.

Preparation of thiazine derivatives

A method for the preparation of a thiazine derivative of the formula STR1 where each R is independently selected from hydrogen or a lower alkyl having 1 to 4 carbon atoms, the method comprising reacting together a sulphur donor which is selected from sulfur, ammonium or alkali metal sulfides, ammonium or alkali metal hydrosulfides, or hydrogen sulfide, 1,1-bis(methylthio)-2-nitroethene and a compound of the formula where each R is as defined above. A preferred method is for the preparation of tetra-2-(nitromethylene)-2H-1,3-thiazine which possesses broad spectrum insecticidal activity, and is also useful as an intermediate in the synthesis of other insecticides.

N-(Arylsulfonyl)-2-nitro-2-(tetrahydro-2H-1,3-thiazin-2-ylidene)acetamides

Novel compounds, identified in the title, useful as insecticides.