Journal
RUSSIAN CHEMICAL BULLETIN
Volume 67, Issue 6, Pages 1059-1064Publisher
SPRINGER
DOI: 10.1007/s11172-018-2180-x
Keywords
3-thioxoperhydroimidazo[4; 5-e]-1; 2; 4-triazin-6-ones; ring contraction; 5-thioxohexahydroimidazo[4; 5-d]imidazol-2(1H)-ones; thioglycolurils; S-alkylation; Triadimefon; fungicidal activity
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A series of 1,3-disubstituted 4-benzylideneamino-5-thioxohexahydroimidazo[4,5-d]imidazol-2(1H)-ones (thioglycolurils) was synthesized via the reaction of 5,7-disubstituted 3-thioxoperhydroimidazo[4,5-e]-1,2,4-triazin-6-ones with hydroxy-, alkoxy-, and fluorocontaining benzaldehyde derivatives. An alkylation of the obtained thioglycolurils with methyl iodide or 4-bromobenzyl bromide provided the corresponding 6-benzylideneamino-5-alkylsulfanyl-3,3a,6,6a-tetrahydroimidazo[4,5-d]imidazol-2(1H)-ones. The fungicidal activity of some synthesized compounds against pathogens causing diseases of agricultural crops was studied.
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