Cyclothiomethylation of heterochain α,ω-diamines with formaldehyde and H2S

Cyclothiomethylation was performed of heterochain (O, S-S, NH) α,ω-diamines with formaldehyde and H2S in aqueous medium at 20–60°C to obtain new α,ω-bis(1,3,5-dithiazinanes). The cyclocondensation of N-(3-aminopropyl)butane-1,4-diamine (spermidine), formaldehyde, and H2S proceeds efficiently in the medium of BuOH-H2O at 0°C and leads to the formation of previously unknown O,S-containing macroheterocycle, 1,7-dioxa-3,5,9,11-tetrathiacyclododecane. A fungicidal activity was found in 5,5′-(3,6-dioxaoctane-1,8-diyl)bis-1,3,5-dithiazinane with respect to microscopic fungi affecting agriculture.