Synthesis and growth regulatory activity of pyrazolesulfanyl- and isoxazolesulfanyl-1H-[1,2,4]triazoles and their azinyl derivatives

Article abstract of DOI:10.1002/jhet.514

By cyclocondensation of 3-(1H-[1,2,4]triazol-3-ylsulfanyl)-pentane-2,4-dion with hydroxylamine, hydrazine, methylhidrazine, and arylsulfonyl-hydrazides, the 3-(3,5-dimethyl-isoxazol-4-ylsulfanyl)-1H-[1,2,4]triazole (2) and 3-(3,5-dimethyl-1-R-pyrazol-4-yl

Full text of DOI:10.1002/jhet.514

188
Synthesis and Growth Regulatory Activity of Pyrazolesulfanyl-
and Isoxazolesulfanyl-1H-[1,2,4]triazoles and Their Azinyl
Derivatives
Vol 48
Karine A. Eliazyan,a Lusya V. Shahbazyan,a Vergush A. Pivazyan,a and
Aleksandr P. Yengoyana,b
*
aLaboratory of Pesticides Synthesis, Armenian State Agrarian University; Teryan 74,
Yerevan 0009, Armenia
bArmenian-Russian (Slavonic) State University; H.Emin 123, Yerevan, 0051, Armenia
*E-mail: ayengoyan@mail.ru
Received February 3, 2010
DOI 10.1002/jhet.514
Published online 7 October 2010 in Wiley Online Library (wileyonlinelibrary.com).
By cyclocondensation of 3-(1H-[1,2,4]triazol-3-ylsulfanyl)-pentane-2,4-dion with hydroxylamine, hy-
drazine, methylhidrazine, and arylsulfonyl-hydrazides, the 3-(3,5-dimethyl-isoxazol-4-ylsulfanyl)-1H-
[1,2,4]triazole (2) and 3-(3,5-dimethyl-1-R-pyrazol-4-ylsulfanyl)-1H-[1,2,4]triazoles (3a–d) are synthe-
sized. Under the action of quaternary ammonium salts of azines with limited heating in acetone they
form a series of compounds (4a–h), which molecules simultaneously contain three different heterocyclic
1
rings. Structures of compounds were confirmed by H and 13C NMR, MS, and elemental analysis. The
plants growth regulatory activities of compounds 4a–h were investigated. Data of biological tests testify
that these compounds can be of interest to search for new growth stimulators.
J. Heterocyclic Chem., 48, 188 (2011).
INTRODUCTION
ring through a sulfur atom, and further substitution in
the position 1 of triazoles to obtain corresponding
azinyl-derivatives.
Among the 1,2,4-triazole derivatives the large number
of fungicides, herbicides, insecticides, and plant growth
stimulators are known that are widely used in agricul-
ture [1]. The majority of these compounds contain in
their molecules a triazole cycle that directly or through
different atomic groups is connected with the substituted
phenyl ring. At the same time, there is a significant in-
terest in searching for potential pesticides among the
compounds, in molecules of which the triazole ring is
connected with other heterocycles directly or through
the heteroatom. Earlier, by regioselective alkylation and
acylation in the position 1 of 3-S-substituted 1H-[1,2,4]
triazoles, we had synthesized a new series of corre-
sponding azinyl derivatives [2,3].
RESULTS AND DISCUSSION
As the initial compound, we used previously synthe-
3-(1H-[1,2,4]triazole-3-ylsulfanyl)-pentane-2,4-
sized
dione 1 [2] that under the action of hydroxylamine and
different hydrazides undergoes a cyclocondensation, and
a new series of compounds 2 and 3 are formed (Scheme
1). The mentioned substances are obtained in suffi-
ciently high yields in the aqueous medium at heating up
to 80ꢀC.
In triazole cycle of the synthesized compounds 2 and 3
the process of the prototropic tautomerism can occur.
Usually the proton exchange between the heteroatoms
proceeds ‘‘fast’’ (in comparison with a temporary NMR-
scale), so in spectra only the averaged signals from two
tautomeric forms are observed. However, in 1H NMR
spectra of compounds 2 and 3 at room temperature two
broadened signals are observed that belong to the protons
for each NH and CH groups of heterocycle. During heat-
ing up to 60ꢀC, when the speed of exchange between the
Among the pyrazole and isoxazole derivatives the
substances with herbicidal [4–14], fungicidal [15–20],
and insecticidal [21–25] activity were also revealed.
However, the number of these preparations is incompa-
rably smaller than the chemical means of plant protec-
tion with triazole, triazine, pyrimidine, thiadiazole, and
thiazole cycles [1]. Therefore, the purpose of the present
research was to synthesize new compounds that contain
pyrazole or isoxazole cycles, connected with triazole
C
V
2010 HeteroCorporation

January 2011
Synthesis and Growth Regulatory Activity of Pyrazolesulfanyl- and
Isoxazolesulfanyl-1H-[1,2,4]triazoles and Their Azinyl Derivatives
189
Scheme 1
(2,3), final products (4), and corresponding methyl-sul-
fanyl derivatives were determined. The assignment of
triazole carbon atoms was made by comparison of
decoupled and proton-coupled spectra of these com-
pounds. Chemical shifts of carbon atoms were compared
with the corresponding data, given in [32]. In this arti-
cle, it was established that if 1-N substitution take place,
the chemical shifts of C3 are in the range of 157.4–
160.3 ppm, but in the case of 4-N-substitution, the peak
of this carbon appears at 149.6–153.1 ppm. In 13C NMR
spectra of the synthesized compounds, the signal of C3
carbon atom is observed in the range of 155.1–160.3
ppm. These data are in agreement with 1-N substitution
in triazole cycle.
BIOLOGICAL ACTIVITY
For preliminary screening tests, the compounds 4a–h
were selected, and growth regulatory activity of their
solutions in concentrations 25 and 50 mg/L was investi-
gated on the swelling, growth, morphogenesis, and sur-
vivability of seeds and seedlings of dicotyledonous cul-
ture plant, French bean. The activity of these com-
pounds was compared with heteroauxin activity. All
investigated substances in a various degree had a stimu-
lator activity (4a-10% compared with heteroauxin; 4b-
95%; 4c-30%; 4d-70%; 4e-40%; 4f-45%; 4g-100%; 4h-
120%). These data testify the necessity of deeper
researches of the growth regulatory activity among the
investigated derivatives. One compound (4h) that sur-
passes heteroauxin on 20% was selected for field trials.
tautomeric forms increases, the signals of the mentioned
protons in pairs coalescence into the single peak.
The synthesized isoxazole- (2) and pyrazole- (3) deriv-
atives under the action of substituted triazine(pyrimi-
dine)-2-yl- (or 4-yl)-trimethyl-ammonium chlorides at
limited heating in acetone form series of compounds (4)
that contain in the molecules simultaneously three differ-
ent heterocyclic rings (Scheme 1). Azinyl-trimethyl-am-
monium chlorides were obtained by substitution of chlo-
rine atoms in 2,4,6-trichloro-[1,3,5]azin. The stepwise
substitution of the first two chlorine atoms proceeds
smoothly, but the substitution of the third chlorine atom
(including interaction with triazole cycle) is problematic.
In such cases, we have proposed to use more electro-
philic azinyl-trimethyl-ammonium chlorides, which are
easily obtained by the interaction of trimethyl-amine
with 4,6-substituted 2-chloro-azins [26,27].
EXPERIMENTAL
The 1H and 13C NMR spectra were determined by Varian
Mercury-300 MHz spectrometer, in the mixture of solvents
DMSO-d6 and CCl4 (1:3), using tetramethylsilane as internal
standard. Mass-spectra were recorded on MX-1321A MS sys-
tem (70 eV). The reaction course control and individuality of
the obtained substances were checked by using the TLC
method on ‘‘Silufol UV-254’’ plates and acetone-hexane mix-
ture (2:1) as eluent. Melting points are uncorrected. Initial 3-
(1H-[1,2,4]triazole-3-ylsulfanyl)-pentane-2,4-dione (1) was pre-
pared as described in [2].
3-(3,5-Dimethyl-isoxazol-4-ylsulfanyl)-1H-[1,2,4]triazole
(2). A mixture of compound 1 (2.0 g; 0.01 mol), hydroxyla-
mine sulfate (0.9 g; 0.11 mol), and potassium carbonate (0.77
g; 0.11 mol) was heated at reflux over a steam bath for 1.5 h.
The mixture was cooled and then the compound 2 was filtered
off and recrystallized from water. The compound was obtained
as white crystals; m.p. 138–139ꢀC, yield: 1.78 g (91%). 1H
NMR: d 2.22 (s, 3H, CH3); 2.48 (s, 3H, CH3); 8.12 (b.s, 1H,
5-H); 13.60 (b.s, 1H, NH). 13C NMR: d 9.9; 11.2; 102.2;
146.0 (C5); 156.1 (C3); 161.7; 173.0. MS (m/z) 196 (Mþ).
Anal. Calcd for C7H8N4OS: C, 42.85; H, 4.11; N, 28.55; S,
16.34. Found: C, 42.55; H, 4.20; N, 28.65; S, 16.61.
In the case of compounds 4, the basic question is at
which position of triazole ring the heterylation reaction
1
occurs. Value of 9.0–9.1 ppm for H-5 in H NMR spec-
tra allows excluding 2-N substitution [28], but do not
make a choice between 1-N and 4-N substitutions. In
some cases, by means of mass spectra a substitution
position in triazole cycle can be established [29–31].
However, in mass spectra of synthesized compounds 4,
the molecular fragments, which allow answering this
question, were not detected. For example, in mass spec-
tra of compounds 4d and 4g, the major registered frag-
ments are for 4d: 318(Mþ,100), 275(22), 165(21),
150(29), 123(54), 43(43) and for 4g: 316(Mþ,52),
283(11), 140(9), 109(100), 56(75), 43(32). For this rea-
son, 13C NMR spectra of some unsubstituted derivatives
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DOI 10.1002/jhet

190
K. A. Eliazyan, L. V. Shahbazyan, V. A. Pivazyan, and A. P. Yengoyan
Vol 48
3-(3,5-Dimethyl-1H-pyrazole-4-ylsulfanyl)-1H-[1,2,4]triazole
1-(4,6-Bis-dimethylamino-[1,3,5]triazin-2-yl)-3-(3,5-dimethyl-
isoxazol-4-yl-sulfanyl)-[1,2,4]-triazole (4a). Purified by recrys-
tallization from benzene. The compound was obtained as white
crystals; m.p. 167–169ꢀC, yield 3.25 g (90%). 1H NMR: d
2.25 (s, 3H, CH3); 2.50 (s, 3H, CH3); 3.18 and 3.22 [s,s,
6H,6H, 4,6-N(CH3)2]; 9.08 (s, 1H, 5-H triazole). MS (m/z) 361
(Mþ). Anal. Calcd for C14H19N9OS: C, 46.52; H, 5.30; N,
34.88. S, 8.87; Found: C, 46.71; H, 5.22; N, 35.10; S, 9.11.
1-(4-Dimethylamino-6-morpholin-4-yl-[1,3,5]triazin-2-yl)-3-
(3,5-dimethyl-isoxazol-4-ylsulfanyl)-[1,2,4]triazole (4b). Purified
by boiling in benzene. The compound was obtained as white
crystals; m.p. 226–228ꢀC, yield: 3.22 g (80%). 1H NMR: d
2.20 (s, 3H, CH3); 2.48 (s, 3H, CH3); 3.18 and 3.23 [s,s,
3H,3H, N(CH3)2]; 3.60–3.70 [m, 4H, O(CH2)2]; 3.83 [b.m, 4H,
N(CH2)2]; 9.06 (s, 1H, 5-H triazole). 13C NMR: d 9.6; 11.1;
35.7; 43.4; 65.6; 101.3; 145.8 (C5); 159.4 (C3); 159.9; 161.5;
164.3; 164.9; 173.0. MS (m/z) 403 (Mþ). Anal. Calcd for
C16H21N9O2S: C, 47.63; H, 5.25; N, 31.24; S, 7.95; Found: C,
47.86; H, 5.21; N, 31.48; S, 8.11.
(3a). The mixture of compound 1 (2.0 g; 0.01 mol) and 5 mL of
63% hydrazine hydrate was allowed to stand at 20ꢀC for 24 h.
The obtained transparent solution (pH > 9) was neutralized with
acetic acid, filtered off and the filtration residue of compound 3a
was washed with 5 mL of H2O, dried in the air and purified by
boiling in toluene. The compound was obtained as white crys-
1
tals; m.p. 218–220ꢀC, yield: 1.48 g (76%). H NMR (60ꢀC): d
2.21 [s, 6H, (CH3)2]; 8.15 (b.s, 1H, 5-H triazole); 13.30 and
13.62 (b.s, 1H, 1H, NH-pyrazole and NH-triazole). MS (m/z)
195 (Mþ). Anal. Calcd for C7H9N5S: C, 43.06; H, 4.65; N,
35.87; S, 16.42; Found: C, 43.24; H, 5.01; N, 35.67; S, 16.25.
3-(1,3,5-Trimethyl-1H-pyrazol-4-ylsulfanyl)-1H-[1,2,4]tri-
azole (3b). At 0ꢀC, 1.44 g (0.01 mol) of methylhydrazine sul-
fate was dissolved with continuous stirring in 20 mL of 10%
sodium hydroxide solution. On reaching to 15ꢀC, 0.01 mol of
compound 1 was added by portions, then the temperature was
raised up to 60ꢀC and the mixture was allowed to stand for 1
h. The mixture was neutralized with acetic acid to pH 7, then
filtered off and the residue of compound 3b was washed with
5 mL of H2O and dried in the air. Purified by recrystallization
from toluene. The compound was obtained as white crystals;
1-(4-Methyl-6-amino-[1,3,5]triazin-2-yl)-3-(3,5-dimethyl-iso-
xazol-4-ylsulfanyl)-[1,2,4]-triazole (4c). Purified by boiling in
benzene. The compound was obtained as white crystals; m.p.
1
1
m.p. 158–160ꢀC, yield: 1.78 g (85%). H NMR (60ꢀC): d 2.13
240–242ꢀC, yield: 2.0 g (66%). H NMR: d 2.19 (s, 3H, CH3);
(s, 3H, CH3); 2.30 (s, 3H, CH3); 3.73 (s, 3H, NCH3); 7.93
(b.s, 1H, 5-H triazole); 13.40 (b.s, 1H, NH). 13C NMR: d 9.7;
11.7; 36.4; 100.6; 143.3; 146.8(C5); 149.5; 156.7 (C3). MS (m/
z) 209 (Mþ). Anal. Calcd for C8H11N5S: C, 45.91; H, 5.30; N,
33.47; S, 15.32; Found: C, 45.70; H, 5.49; N, 33.63; S, 15.50.
3-[1-(Toluene-4-sulfonyl)-3,5-dimethyl-1H-pyrazol-4-ylsul-
fanyl]-1H-[1,2,4]-triazole (3c). The suspension of compound
1 (2.0 g; 0.01 mol) and para-toluenesulfonyl hydrazine (1.86
g; 0.01 mol) in 10 mL of H2O was heated at 60ꢀC for 3 h.
The water was decanted, viscous oil processed with ice-cold
water and the sediment of compound 3c filtered off. Purified
by recrystallization from benzene. The compound was obtained
as white crystals; m.p. 150–152ꢀC, yield: 3.07 g (88%). 1H
NMR (60ꢀC): d 2.20 (s, 3H, CH3); 2.45 (s, 3H, CH3-tolyl);
2.62 (s, 3H, CH3); 7.36–7.85 (m, 4H, C6H4); 8.20 (b.s, 1H, 5-
H triazole); 13.80 (b.s, 1H, NH). MS (m/z) 349 (Mþ). Anal.
Calcd for C14H15N5O2S2: C, 48.12; H, 4.33; N, 20.04; S,
18.35; Found: C, 48.36; H, 4.60; N, 20.31; S, 18.49.
2.37 (s, 3H, 4-CH3); 2.50 (s, 3H, CH3); 6.40 (b.s, 2H, NH2);
9.03 (s, 1H, 5-H triazole). MS (m/z) 304 (Mþ). Anal. Calcd
for C11H12N8OS: C, 43.41; H, 3.97; N, 36.82; S, 10.54; Found:
C, 43.13; H, 4.01; N, 36.61; S, 10.74.
1-(4-Methoxy-6-methyl-pyrimidin-2-yl)-3-(3,5-dimethyl-isoxa-
zol-4-ylsulfanyl)-[1,2,4]-triazole (4d). Purified by recrystalliza-
tion from the mixture of benzene:hexane (1:1). The compound
was obtained as white crystals; m.p. 153–155ꢀC, yield: 2.48 g
(78%). 1H NMR: d 2.25 (s, 3H, CH3); 2.48 (s, 3H, 4-CH3);
2.55 (s, 3H, CH3); 4.03 (s, 3H, CH3); 6.62 (s, 1H, 5-H-pyrim.);
9.10 (s, 1H, 5-H triazole). 13C NMR: d 9.9; 11.3; 23.3; 54.4;
101.3; 105.2; 145.9 (C3); 152.5; 160.3 (C3); 161.8; 169.7;
170.8; 173.4. MS (m/z) 318 (Mþ). Anal. Calcd for
C13H14N6O2S: C, 49.05; H, 4.43; N, 26.40; S, 10.07; Found:
C, 49.27; H, 4.65; N, 26.69; S, 10.29.
1-(4,6-Bis-dimethylamino-[1,3,5]triazin-2-yl)-3-(1,3,5-trimethyl-
1H-pyrazol-4-ylsulfanyl)-[1,2,4]-triazole (4e). Purified by recrys-
tallization from benzene. The compound was obtained as white
crystals; m.p. 186–188ꢀC, yield: 2.92 g (78%). 1H NMR: d
2.20 (s, 3H, CH3); 2.33 (s, 3H, CH3); 3.17 and 3.22 [s,s,
6H,6H, N(CH3)2]; 3.75 (s, 3H, NCH3); 9.00 (s, 1H, 5-H tria-
zole). 13C NMR: d 9.8; 11.8; 35.7; 36.4; 100.0; 143.4;
145.6(C5); 149.7; 159.3(C3); 161.9; 164.9. MS (m/z) 374
(Mþ). Anal. Calcd for C15H22N10S: C, 48.11; H, 5.92; N,
37.40; S, 8.56; Found: C, 47.84; H, 6.21; N, 37.20; S, 8.38.
1-(4-Dimethylamino-6-morpholin-4-yl-[1,3,5]triazin-2-yl)-3-(1,
3,5-trimethyl-1H-pyrazol-4-ylsulfanyl)-[1,2,4]triazole (4f). Purified
by recrystallization from benzene. The compound was obtained
as white crystals; m.p. 152–154ꢀC, yield: 3.75 g (90%). 1H
NMR: d 2.20 (s, 3H, CH3); 2.32 (s, 3H, CH3); 3.17 and 3.23
[s,s, 3H,3H, N(CH3)2]; 3.63–3.70 [m, 4H, O(CH2)2]; 3.73 (s,
3H, NCH3); 3.82 [b.m, 4H, N(CH2)2]; 9.00 (s, 1H, 5-H tria-
zole). MS (m/z) 416 (Mþ). Anal. Calcd for C17H24N10OS: C,
49.02; H, 5.81; N, 33.63; S, 7.70; Found: C, 48.79; H, 6.03;
N, 33.81; S, 7.93.
3-(1-Benzenesulfonyl-3,5-dimethyl-1H-pyrazol-4-ylsulfanyl)-
1H-[1,2,4]triazole (3d). 3-(1-Benzenesulfonyl-3,5-dimethyl-1H-
pyrazol-4-ylsulfanyl)-1H-[1,2,4]triazole (3d) was obtained
according to the mentioned above description. Purified by
recrystallization from benzene. The compound was obtained as
1
white crystals; m.p. 130–132ꢀC, yield: 2.95 g (88%). H NMR
(60ꢀC): d 2.18 (s, 3H, CH3); 2.62 (s, 3H, CH3); 7.58–8.00 (m,
5H, C6H5); 8.15 (b.s, 1H, 5-H triazole); 13.70 (b.s, 1H, NH).
MS (m/z) 335 (Mþ). Anal. Calcd for C13H13N5O2S2: C, 46.55;
H, 3.91; N, 20.88; S, 19.12; Found: C, 46.44; H, 4.17; N,
21.11; S, 19.40.
Synthesis of compounds 4a–h.
General procedure. Compound 2 (or 3) (0.01 mol) was
added with continuous stirring to suspension of 0.01 mol KOH
in 20 mL of dry acetone. In an hour at 0ꢀC, 0.01 mol of azi-
nyltrimethylammonium chloride was added. The reaction mix-
ture was stirred at 20ꢀC for 5 h, then at 50–52ꢀC for 2 h. The
suspension was evaporated, the residue was washed with
water, and then the compound 4 was filtered off and dried in
the air.
1-(2-Amino-6-methyl-pyrimidin-4-yl)-3-(1,3,5-trimethyl-1H-pyr-
azol-4-ylsulfanyl)-[1,2,4]triazole (4g). Purified by boiling in
benzene. The compound was obtained as white crystals; mp
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Synthesis and Growth Regulatory Activity of Pyrazolesulfanyl- and
Isoxazolesulfanyl-1H-[1,2,4]triazoles and Their Azinyl Derivatives
191
236–237ꢀC, yield: 2.84 g (90%). 1H NMR: d 2.19 (s, 3H,
CH3); 2.32 (s, 3H, CH3); 2.37 (s, 3H, 6-CH3); 3.76 (s, 3H,
NCH3); 6.42 (b.s, 2H, NH2); 6.72 (s, 1H, 5-H pyrim.); 8.97 (s,
1H, 5-H triazole). 13C NMR: d 9.8; 11.8; 23.85; 36.4; 96.1;
99.6; 143.2 (C5); 143.5; 149.7; 155.1 (C3); 162.3; 162.9;
171.1. MS (m/z) 316 (Mþ). Anal. Calcd for C13H16N8S: C,
49.35; H, 5.10; N, 35.42; S, 10.13; Found: C, 49.24; H, 5.31;
N, 35.70; S, 10.17.
1-(4-Methoxy-6-methyl-pyrimidin-2-yl)-3-(1,3,5-trimethyl-1H-
pyrazol-4-yl-sulfanyl)-[1,2,4]triazole (4h). Purified by recrys-
tallization from the mixture of benzene:hexane(1:1). The com-
pound was obtained as white crystals; m.p. 236–237ꢀC, yield:
2.71 g (82%). 1H NMR: d 2.20 (s, 3H, CH3); 2.35 (s, 3H,
CH3); 2.47 (s, 3H, 4-CH3); 3.75 (s, 3H, NCH3); 4.05 (s, 3H,
OCH3); 6.60 (s, 1H, 5-H pyrim.); 9.02 (s, 1H, 5-H triazole).
MS (m/z) 331 (Mþ). Anal. Calcd for C14H17N7OS: C, 50.74;
H, 5.17; N, 29.59; S, 9.68; Found: C, 50.85; H, 5.42; N,
29.92; S, 10.02.
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Journal of Heterocyclic Chemistry
DOI 10.1002/jhet