Synthesis and Fungicidal Activity
V. R. Akhmetova
, Z. T. Niatshina
, A. D. Burakaeva
, N. F. Galimzyanova
, and R. V. Kunakova
Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, Ufa, Bashkortostan, Russia
Bashkir State University, Ufa, Bashkortostan, Russia
Institute of Biology, Ufa Scientific Center, Russian Academy of Sciences, Ufa, Bashkortostan, Russia
Received April 16, 2010
Abstract—Thiomethylation of para-toluidine and 4(5)-methyl-2-aminothiazoles was used to synthesize N,N'-
dithol-4-yl-1,3,5-thiadiazinane and N,N'-[methylene-bis-(thiomethylene)]-bis-[4(5)-methyl-1,3-thiazole-2-
amines]. A fungicidal and fungistatic effect toward some microscopic fungi, plant-disease-producing factor,
was revealed for these compounds.
ORGANIC SYNTHESIS AND INDUSTRIAL
ISSN 1070-4272, Russian Journal of Applied Chemistry, 2011, Vol. 84, No. 3, pp. 416–419. © Pleiades Publishing, Ltd., 2011.
Original Russian Text © V.R. Akhmetova, Z.T. Niatshina, A.D. Burakaeva, N.F. Galimzyanova, R.V. Kunakova, 2011, published in Zhurnal Prikladnoi
Khimii, 2011, Vol. 84, No. 3, pp. 424–427.
Aromatic compounds conjugated with S,N-con-
taining heterorings play an important role in biotic and
abiotic nature. For example, aryl-containing 1,3,5-
thiadiazinanes are used as fungicides, insecticides,
herbicides, and bactericides [1–3].
An effective way to synthesize compounds of this
kind is by multicomponent condensation of anilines
with formaldehyde and hydrogen sulfide, which makes
it possible to construct 1,3,5-dithiazines and 1,3,5-
thiadiazinanes in a single stage [4–7].
To synthesize compounds with a fungicidal
activity, we studied the thiomethylation of para-
toluidine (Ia) and 4- (Ib) and 5-methyl-2-amino-
thiazoles (Ic) with formaldehyde and hydrogen sulfide.
The starting amino substrates Ia–Ic were chosen
because syntheses of fungicides from para-toluidine
and thiazoles, described in the literature, are complex
and require difficultly accessible reagents [8, 9]. In
addition, thiazole derivatives possess a wide variety of
biological properties: the thiazole ring enters into the
composition of vitamin B
, penicillin, carboxylase
enzyme, and other natural compounds .
Based on an analysis of the condensation reaction
conditions (temperature, concentration, and order of
O + H