The synthesis and fungicidal activities of 2,6-bis[(3-aryl)-s-triazolo[3,4- b]-[1,3,4]thiadiazole-6-yl]pyridines

Article abstract of DOI:10.1080/10426500600605830

In search of better bioactive compounds, a series of novel 2,6-bis[(3-aryl)-s-triazolo[3,4-b]-[1,3,4]thiadiazole-6-yl]pyridines 2 were synthesized in high yields by the cyclization of 3-aryl-4-amino-5-mercapto-1, 2, 4-triazoles 1 with 2,6-pyridine dicarboxylic acid. 2 exhibited good fungicidal activities against Cerospora beticola sacc. Copyright Taylor & Francis Group, LLC.

Full text of DOI:10.1080/10426500600605830

This article was downloaded by: [New York University]
On: 02 June 2013, At: 14:02
Publisher: Taylor & Francis
Informa Ltd Registered in England and Wales Registered Number: 1072954
Registered office: Mortimer House, 37-41 Mortimer Street, London W1T 3JH,
UK
Phosphorus, Sulfur, and Silicon
and the Related Elements
Publication details, including instructions for
authors and subscription information:
http://www.tandfonline.com/loi/gpss20
The Synthesis and Fungicidal
Activities of 2,6-Bis[(3-
aryl)-s-triazolo[3,4-b]-
[1,3,4]thiadiazole-6-
yl]pyridines
Dejiang Li a , Deqing Long a & Heqing Fu b
a Department of Chemistry, Yunyang Teachers
College, Danjiangkou, P. R. China
b Research Institute of Chemical Engineering, South
China University of Technology, Guangzhou, P. R.
China
Published online: 21 Sep 2006.
To cite this article: Dejiang Li , Deqing Long & Heqing Fu (2006): The Synthesis
and Fungicidal Activities of 2,6-Bis[(3-aryl)-s-triazolo[3,4-b]-[1,3,4]thiadiazole-6-
yl]pyridines, Phosphorus, Sulfur, and Silicon and the Related Elements, 181:9,
2079-2087
To link to this article: http://dx.doi.org/10.1080/10426500600605830
PLEASE SCROLL DOWN FOR ARTICLE
Full terms and conditions of use: http://www.tandfonline.com/page/terms-
and-conditions
This article may be used for research, teaching, and private study purposes.
Any substantial or systematic reproduction, redistribution, reselling, loan,
sub-licensing, systematic supply, or distribution in any form to anyone is
expressly forbidden.

The publisher does not give any warranty express or implied or make any
representation that the contents will be complete or accurate or up to
date. The accuracy of any instructions, formulae, and drug doses should be
independently verified with primary sources. The publisher shall not be liable
for any loss, actions, claims, proceedings, demand, or costs or damages
whatsoever or howsoever caused arising directly or indirectly in connection
with or arising out of the use of this material.

Phosphorus, Sulfur, and Silicon, 181:2079–2087, 2006
Copyright © Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426500600605830
The Synthesis and Fungicidal Activities of 2,6-Bis[(3-aryl)-
s-triazolo[3,4-b]-[1,3,4]thiadiazole-6-yl]pyridines
Dejiang Li
Deqing Long
Department of Chemistry, Yunyang Teachers College, Danjiangkou,
P. R. China
Heqing Fu
Research Institute of Chemical Engineering, South China University
of Technology, Guangzhou, P. R. China
In search of better bioactive compounds, a series of novel 2,6-bis[(3-aryl)-s-
triazolo[3,4-b]-[1,3,4]thiadiazole-6-yl]pyridines 2 were synthesized in high yields
by the cyclization of 3-aryl-4-amino-5-mercapto-1, 2, 4-triazoles 1 with 2,6-pyridine
dicarboxylic acid. 2 exhibited good fungicidal activities against Cerospora beticola
sacc.
Keywords 3-aryl-4-amino-5-mercapto-1,2,4-triazole; 2,6-bis[(3-aryl)-s-triazolo[3,4-b]-
[1,3,4] thiadiazole-6-yl]pyridines; fungicidal activities; synthesis
INDRODUCTION
s-triazolo[3,4-b]-[1,3,4]thiadiazole derivatives possess significant
biological activitites, such as antiflammatory, and antiviral, antifun-
gal, antineoplastic, and antidepressant effects1−2 and electrochemical
properties.3 They are highly important heterocycles and have been
used in the research and development of agrochemicals and in the
pharmaceutical chemistry. Most derivatives reported only contain one
s-triazolo[3,4-b]-[1,3,4]thiadiazole unit in one moleclule.4−11 Recently,
some of the bis[1,2,4-triazolo[3,4-b]-[1,3,4]thiadiazole-4-yl]alkanes
were reported to posses antibacterial property,12 and bis[1,2,4-
triazolo[3,4-b]-[1,3,4]thiadiazole-3-ylmethoxy]phenylenes
posses
Received November 14, 2005; accepted December 9, 2005.
We gratefully acknowledge financial support of this work by the Natural Science Foun-
dation of Hubei Province Education Committee of China (Project No. D200660001).
Address correspondence to Dejiang Li, Department of Chemistry, Yunyang Teachers
College, Danjiangkou, 442700 P. R. China. E-mail: lidejiang999@yahoo.com.cn
2079

2080
D. Li et al.
anticancer activity against a panel of 60 cell lines derived from 7
cancer types, namely lung, colon, melanoma, renal, ovarian, CNS, and
leukemia.13 Prompted by these observations and in continuation of our
search for bioactive molecules, we designed the synthesis of a series of
novel 2,6-bis[(3-aryl)-s-triazolo[3,4-b]-[1,3,4]thiadiazole-6-yl]pyridines
by the cyclization of 3-aryl-4-amino-5-mercapto-1,2,4-triazoles with
2,6-pyridine dicarboxylic acid. The synthesis, characterization, and
results of fungicidal activity screening studies of the newly synthesized
compounds are presented in this article.
RESULTS AND DISCUSSION
Aroylhydrazides were prepared by the esterification and hydrazinolysis
of corresponding aromatic carboxylic acids. The reaction of
aroylhydrazides with CS2/KOH in absolute ethanol gave potas-
sium aroyldithiocarbazates, and then the hydrazinolysis of potassium
aroyldithiocarbazates with hydrazine hydrate afforded 3-aryl-4-amino-
5-mercapto-1,2,4-triazoles 1 (Scheme 1).
SCHEME 1
The synthesis of 2,6-bis[(3-aryl)-s-triazolo[3,4-b]-[1,3,4]thiadiazole-
6-yl] pyridines
2 was accomplished in one step with good
yields by condensing 3-aryl-4-amino-5-mercapto-1,2,4-triazoles 1 with
2,6-pyridine dicarboxylic acid in the presence of POCl3 and tetra-
butylammonium iodide (Scheme 2, Table I). Because of the poor sol-
ubility of 1 and 2,6-pyridine dicarboxylic acid in POCl3, the yield
of 2 is very low. For example, the yield of 2g was 25.3%. However,
where the tetrabutylammonium iodide as a phase transfer catalyst
was utilized and the mixture was first stirred for 6 h at 55–60◦C,
and then refluxed for 10 h at 115–120◦C, 2g was obtained in a 71%
yield.
The structures of all compounds 2a–p were established on the basis of
elemental analysis and spectral data. The IR spectral data of

Synthesis and Fungicidal Activities
2081
SCHEME 2
compounds 2 showed bands at 1610–1635 cm−1, 1230–1260 cm−1, and
1
700 cm−1 due to C=N, N-N=C, and C-S-C, respectively. The H NMR
spectra of 2 exhibited multiple signals in the δ 7.00–8.80 range ac-
counting for hydrogen of aryl group. With compound 2g as an example,
it exhibited multiple signals in the δ 8.78–8.74, 8.52–8.26, and 7.59–
7.55 ranges accounting for the 11 hydrogens of phenyl and pyridyl
groups. A sharp singlet at δ 2.56 integrating for 6 protons is attributed
to the CH3 groups. The EI-MS for compounds 2 exhibited molecular
ion peaks. With compound 2g as an example, it showed a strong molec-
ular ion peak M+ with m/z 507 and 59% relative abundance.
The biological activity of compounds 2 were investigated, and the re-
sults showed that they exhibited fungicidal activities, especially against
TABLE I The Preparation of
2,6-Bis[(3-aryl)-s-triazolo[3,4-b]-[1,3,4]thiadiazole-6-yl]pyridines 2
from 3-Aryl-4-amino-5-mercapto-1, 2, 4-triazoles 1
Entry
Ar
Condition
Yield (%)a
M.P. (◦C)
2a
2b
2c
2d
2e
2f
2g
2h
2i
2j
2k
2l
2m
2n
2o
2p
Ph
115–120◦C/9.0 h
115–120◦C/10 h
115–120◦C/11 h
115–120◦C/11 h
115–120◦C/10 h
115–120◦C/11 h
115–120◦C/12 h
115–120◦C/10 h
115–120◦C/12 h
115–120◦C/11 h
115–120◦C/10 h
115–120◦C/11 h
115–120◦C/13 h
115–120◦C/11 h
115–120◦C/12 h
115–120◦C/9.0 h
72
56
60
67
56
54
71
62
66
58
63
71
68
55
51
50
>300
>300
>300
>300
>300
>300
>300
>300
>300
>300
>300
>300
>300
>300
>300
>300
2-Cl-Ph
3-Cl-Ph
4-Cl-Ph
2-CH3-Ph
3-CH3-Ph
4-CH3-Ph
3-Br-Ph
4-Br-Ph
2-I-Ph
3-I-Ph
4-I-Ph
4-OCH3-Ph
4-Pyridyl
3-Pyridyl
2-Furyl
aPurified yields of 2a–2p 2,6-pyridine dicarboxylic acid.

2082
D. Li et al.
TABLE II The Fungicidal Activities of
2,6-Bis[(3-aryl)-s-triazolo[3,4-b]-[1,3,4]thiadiazole-6-yl]
Pyridines 2 (50 mg/L, Relative Inhibition %)
Gibberella
zeae
Cerospora
beticola sacc
Physalospora
piricola
Pellicularia
sasakii
Entry
2a
2b
2c
2d
2e
2f
2g
2h
2i
2j
2k
2l
2m
2n
2o
2p
20
45
58
70
26
35
39
32
30
28
26
29
32
48
52
38
73
90
91
95
78
74
70
75
80
84
86
80
70
90
88
77
59
78
80
76
65
62
56
45
42
38
41
46
26
70
65
72
15
80
89
84
29
32
25
40
45
32
28
24
33
36
42
51
Cerospora beticola sacc. For example, 2d showed 95% of Cerospora beti-
cola sacc inhibition of in 50 mg/L (see Table II).
CONCLUSION
In conclusion, tetrabutylammonium iodide is an efficient catalyst
for the synthesis of 2,6-bis[(3-aryl)-s-triazolo[3,4-b]-[1,3,4]thiadiazole-
6-yl]pyridines by the reaction of 3-aryl-4-amino-5-mercapto-1, 2, 4-
triazoles with 2,6-pyridine dicarboxylic acid. Among all the compounds
tested, 2d showed a high degree of inhibition against Cerospora beticola
sacc. Hence, compound 2d stands to be a promising fungicidal agent.
EXPERIMENTAL
Melting points were determined on an X4 melting point apparatus and
are uncorrected. IR spectra were recorded on a Nicolet Nexus 470 FT-
IR spectrophotometer using KBr discs in the range 4000–400 cm−1
.
1H NMR spectra were recorded on a Varian Mercury-Plus 400 NMR
spectrometer in CF3COOD or pyridine-d5 solution using TMS as an
internal reference. MS spectra were recorded on a Finnigan Trace

Synthesis and Fungicidal Activities
2083
GC-MS spectrometer. Elemental analyses were taken on a Perkin-
Elemer-2400-CHN elemental analysis instrument.
The General Procedure for the Preparation
of 3-Aryl-4-amino-5-mercapto-1, 2, 4-triazole 114
A mixture of potassium aroyldithiocarbazate (30 mmol) and hydrazine
hydrate (80%, 36 mL) was refluxed with stirring for 4–5 h at 120◦C.
The color of the reaction mixture changed to green, and a homogeneous
solution resulted. Acidification with HCl (3 mol/L) resulted in the pre-
cipitation of a white solid. The product was filtered, washed with cold
water, and recrystallized from ethanol to give the pure compounds 1a–p.
The General Procedure for the Preparation of 2,6-Bis[(3-aryl)-
s-triazolo[3,4-b]-[1,3,4]-thiadiazole-6-yl]pyridines 215
A mixture of compounds 3-aryl-4-amino-5-mercapto-1,2,4-triazole
(2.2 mmol), 2,6-pyridine dicarboxylic acid (1.67 g, 1.0 mmol), the phase
transfer catalyst tetrabutylammonium iodide (1.85 g, 0.5 mmol), and
POCl3 (7 mL) was stirred for 4 h at 55–60◦C and then refluxed for 9.0–
13 h at 115–120◦C. Excess POCl3 was removed under reduced pres-
sure. The concentrated mass was cooled and poured into crushed ice
and neutralized with potassium carbonate. The separated solid was fil-
tered, washed with water, washed with ethanol, and then dried. The
crude material was recrystallized (ethanol-pyridine), giving the pure
products 2a–p.
2,6-Bis[(3-phenyl)-s-triazolo[3,4-b]-[1,3,4]thiadiazole-6-
yl]pyridine (2a)
Yellow powder, 1H NMR (Pyridine-d5, 400 MHz): δ 8.62–8.53 (m, 4H,
Ar-H), 8.42–8.21 (m, 4H, Ar-H), 7.79–7.56 (m, 5H, Ar-H); IR (KBr, cm−1):
1612, 1251, 700. MS-EI (m/z): 479 (M+, 2%), 304 (3%), 146 (51%), 102
(100%). Elemental anal. calcd. for C23H13N9S2: C, 57.61; H, 2.73; N,
26.29. Found: C, 57.76; H, 2.62; N, 26.18.
2,6-Bis[(3-o-chlorophenyl)-s-triazolo[3,4-b]-[1,3,4]-thiadiazole-
6-yl]pyridine (2b)
Brown powder, 1H NMR (Pyridine-d5, 400 MHz): δ 8.47–8.39 (m,
4H, Ar-H), 8.31–8.23 (m, 3H, Ar-H), 7.82–7.71 (m, 4H, Ar-H); IR (KBr,
cm−1): 1619, 1244, 697; MS-EI (m/z): 547 (M+, 58%), 549 (M+2, 15%),
357 (38%), 338 (100%), 146 (51%), 102 (49%). Elemental anal. calcd. for
C23H11N9S2Cl2: C, 52.56; H, 2.02; N, 22.99. Found: C, 52.43; H, 2.11; N,
22.79.

2084
D. Li et al.
2,6-Bis[(3-m-chlorophenyl)-s-triazolo[3,4-b]-[1,3,4]thiadiazole-
6-yl]pyridine (2c)
Brown powder, 1H NMR (Pyridine-d5, 400 MHz): δ 8.63–8.59 (m,
2H, Ar-H), 8.52–8.26 (m, 5H, Ar-H), 7.85–7.69 (m, 4H, Ar-H); IR (KBr,
cm−1): 1621, 1248, 701; MS-EI (m/z): 547 (M+, 100%), 549 (M + 2, 38%),
357 (67%), 338 (69%), 146 (56%), 102 (62%). Elemental anal. calcd. for
C23H11N9S2Cl2: C, 52.56; H, 2.02; N, 22.99. Found: C, 52.68; H, 2.01; N,
22.87.
2,6-Bis[(3-p-chlorophenyl)-s-triazolo[3,4-b]-[1,3,4]-
thiadiazole-6-yl]pyridine (2d)
Brown powder, 1H NMR (Pyridine-d5, 400 MHz): δ 8.59–8.51 (m,
3H, Ar-H), 8.40–8.17 (m, 4H, Ar-H), 7.74–7.60 (m, 4H, Ar-H); IR (KBr,
cm−1): 1630, 1254, 702; MS-EI (m/z): 547 (M+, 100%), 549 (M + 2, 25%),
357 (42%), 338 (52%), 146 (63%), 102 (74%). Elemental nal. calcd. for
C23H11N9S2Cl2: C, 52.56; H, 2.02; N, 22.99. Found: C, 52.71; H, 2.13; N,
22.82.
2,6-Bis[(3-o-methylphenyl)-s-triazolo[3,4-b]-[1,3,4]-
thiadiazole-6-yl]-pyridine (2e)
1
Pale yellow powder, H NMR (Pyridine-d5, 400 MHz): δ 8.73–8.62
(m, 3H, Ar-H), 8.42–8.24 (m, 4H, Ar-H), 7.69–7.51 (m, 4H, Ar-H), 2.53
(s, 6H, 2CH3); IR (KBr, cm−1): 1628, 1241, 701; MS-EI (m/z): 507 (M+,
38%), 317 (52%), 147 (19%), 117 (60%), 115 (100%). Elemental anal.
calcd. for C25H17N9S2: C, 59.16; H, 3.38; N, 24.83. Found: C, 59.02; H,
3.42; N, 24.95.
2,6-Bis[(3-m-methylphenyl)-s-triazolo[3,4-b]-[1,3,4]-
thiadiazole-6-yl]-pyridine(2f)
Yellow powder, 1H NMR (Pyridine-d5, 400 MHz): δ 8.72–8.60 (m, 4H,
Ar-H), 8.69–8.38 (m, 5H, Ar-H), 7.59–7.55 (m, 2H, Ar-H), 2.54 (s, 6H,
2CH3); IR (KBr, cm−1): 1635, 1250, 701; MS-EI (m/z): 507 (M+, 42%), 317
(31%), 147 (37%), 117 (51%), 115 (100%), 102 (32%). Elemental anal.
calcd. for C25H17N9S2: C, 59.16; H, 3.38; N, 24.83. Found: C, 59.23; H,
3.43; N, 24.78.
2,6-Bis[(3-p-methylphenyl)-s-triazolo[3,4-b]-[1,3,4]-
thiadiazole-6-yl]-pyridine (2g)
Yellow powder, 1H NMR (Pyridine-d5, 400 MHz): δ 8.78–8.74 (m, 2H,
Ar-H), 8.52–8.26 (m, 5H, Ar-H), 7.59–7.55 (m, 4H, Ar-H), 2.56 (s, 6H,
2CH3); IR (KBr, cm−1): 1632, 1256, 702; MS-EI (m/z): 507 (M+, 59%),
317 (49%), 147 (27%), 117 (42%), 115 (100%), 101 (20%). Elemental anal.

Synthesis and Fungicidal Activities
2085
calcd. for C25H17N9S2: C, 59.16; H, 3.38; N, 24.83. Found: C, 59.28; H,
3.39; N, 24.72.
2,6-Bis[(3-m-bromophenyl)-s-triazolo[3,4-b]-[1,3,4]-
thiadiazole-6-yl]pyridine (2h)
Pale yellow powder, 1H NMR (CF3COOD, 400 MHz): δ 8.79–8.65 (m,
3H, Ar-H), 8.24–8.21 (m, 5H, Ar-H), 7.85–7.74 (m, 3H, Ar-H); IR (KBr,
cm−1): 1623, 1239, 703; MS-EI (m/z): 635 (M+, 11%), 637 (M + 2, 12%),
400 (3%), 382 (35%), 146 (47%), 102 (100%). Elemental anal. calcd. for
C23H11N9S2Br2: C, 43.34; H, 1.74; N, 19.78. Found: C, 43.42; H, 1.70; N,
19.65.
2,6-Bis[(3-p-bromophenyl)-s-triazolo[3,4-b]-[1,3,4]-
thiadiazole-6-yl]pyridine (2i)
Yellow powder, 1H NMR (CF3COOD, 400 MHz): δ 8.78–8.51 (m, 4H,
Ar-H), 8.27–8.24 (m, 4H, Ar-H), 7.92–7.88 (m, 3H, Ar-H); IR (KBr,
cm−1): 1617, 1245, 701; MS-EI (m/z): 635 (M+, 13%), 637 (M + 2, 18%),
400 (7%), 381 (4%), 146 (51%), 102 (100%). Elemental anal. calcd. for
C23H11N9S2Br2: C, 43.34; H, 1.74; N, 19.78. Found: C, 43.27; H, 1.72; N,
19.91.
2,6-bis[(3-o-iodophenyl)-s-triazolo[3,4-b]-[1,3,4]-
thiadiazole-6-yl]-pyridine (2j)
Yellow powder, 1H NMR (CF3COOD, 400 MHz): δ 8.70–8.59 (m, 5H,
Ar-H), 8.26–8.12 (m, 4H, Ar-H), 8.02–7.92 (m, 2H, Ar-H); IR (KBr, cm−1):
1625, 1231, 700; MS (m/z): 731 (M+, 6%), 430 (52%), 146 (29%), 129
(15%), 102 (100%). Anal. calcd. for C23H11N9S2I2: C, 37.77; H, 1.52; N,
17.24. Found: C, 37.84; H, 1.50; N, 17.18.
2,6-bis[(3-m-iodophenyl)-s-triazolo[3,4-b]-[1,3,4]-
thiadiazole-6-yl]-pyridine (2k)
1
Pale yellow powder, H NMR (Pyridine-d5, 400 MHz): δ 8.67–8.38
(m, 4H, Ar-H), 8.24–8.12 (m, 4H, Ar-H), 7.85–7.78 (m, 3H, Ar-H); IR
(KBr, cm−1): 1621, 1262, 700; MS-EI (m/z): 731 (M+, 51%), 675 (7%),
430 (76%), 146 (26%), 129 (6%), 102 (44%), 92 (100%). Anal. calcd. for
C23H11N9S2I2: C, 37.77; H, 1.52; N, 17.24. Found: C, 37.86; H, 1.67; N,
17.13.
2,6-bis[(3-p-iodophenyl)-s-triazolo[3,4-b]-[1,3,4]-
thiadiazole-6-yl]-pyridine (2l)
Yellow powder, 1H NMR (CF3COOD, 400 MHz): δ 8.73–8.42 (m, 4H,
Ar-H), 8.11–8.04 (m, 5H, Ar-H), 7.93–7.89 (m, 2H, Ar-H); IR (KBr, cm−1):
1627, 1238, 703; MS-EI (m/z): 731 (M+, 5%), 430 (67%), 146 (44%), 129

2086
D. Li et al.
(9%), 102 (100%). Anal. calcd. for C23H11N9S2I2: C, 37.77; H, 1.52; N,
17.24. Found: C, 37.64; H, 1.49; N, 17.32.
2,6-Bis[(3-p-methoxyphenyl)-s-triazolo[3,4-b]-[1,3,4]-
thiadiazole-6-yl]pyridine (2m)
Yellow powder, 1H NMR (Pyridine-d5, 400 MHz): δ 8.71–8.64 (m, 2H,
Ar-H), 8.47–8.18 (m, 5H, Ar-H), 7.69–7.63 (m, 4H, Ar-H), 3.89 (s, 6H,
2OCH3); IR (KBr, cm−1): 1616, 1241, 700; MS-EI (m/z): 540 (M+, 54%),
334 (84%), 146 (48%), 132 (100%), 101(58%). Elemental anal. calcd. for
C25H17N9S2O2: C, 55.65; H, 3.18; N, 23.36. Found: C, 55.74; H, 3.12; N,
23.27.
2,6-Bis[(3-4ꢀ-pyridyl)-s-triazolo[3,4-b]-[1, 3, 4]thiadiazole-6-yl]-
pyridine (2n)
1
Yellow powder, H NMR (Pyridine-d5, 400 MHz): 8.47–8.43 (m, 2H,
Ar-H), 8.38–8.35 (m, 3H, Ar-H), 8.24–8.17 (m, 4H, Ar-H), 7.42–7.38
(m, 2H, Ar-H); IR (KBr, cm−1): 1626, 1256, 700; MS-EI (m/z): 481 (M+,
100%), 323 (23%), 305 (45%), 146 (16%), 104 (10%). Elemental anal.
calcd. for C21H11N11S2: C, 52.38; H, 2.30; N, 32.01. Found: C, 52.27; H,
2.11; N, 32.18.
2,6-Bis[(3-3ꢀ-pyridyl)-s-triazolo[3, 4-b]-[1, 3, 4]thiadiazole-6-yl]-
pyridine (2o)
Pale yellow powder, 1H NMR (Pyridine-d5, 400 MHz): 8.67–8.51 (m,
3H, Ar-H), 8.42–8.33 (m, 4H, Ar-H), 8.28–8.11 (m, 2H, Ar-H), 7.46–7.32
(m, 2H, Ar-H); IR (KBr, cm−1): 1621, 1242, 701; MS-EI (m/z): 481 (M+,
100%), 323 (15%), 305 (71%), 146 (32%), 104 (9%). Elemental anal. calcd.
for C21H11N11S2: C, 52.38; H, 2.30; N, 32.01. Found: C, 52.47; H, 2.28;
N, 31.87.
2,6-Bis[(3-2ꢀ-furyl)-s-triazolo[3, 4-b]-[1, 3, 4]-
thiadiazole-6-yl]pyridine (2p)
Pale yellow powder, 1H NMR (Pyridine-d5, 400 MHz): 8.43–8.25 (m,
3H, Ar-H), 7.24–6.67 (m, 6H, furyl-H); IR (KBr, cm−1): 1617, 1251, 700;
MS-EI (m/z): 459 (M+, 41%), 312 (4%), 294 (64%), 146 (100%), 93 (31%).
Elemental anal. calcd. for C19H9N9O2S2: C, 49.67; H, 1.97; N, 27.44.
Found: C, 49.75; H, 2.11; N, 27.33.
REFERENCES
[1] N. F. Ewiss and A. A. Bahajaj, J. Heterocylic Chem., 24, 1173 (1987).
[2] M. Jan and G. S. R. Anjaneyulu, Indian J. Chem., 27B, 128 (1987).
[3] X. Xiong, L. X. Zhang, A. J. Zhang and X. Sh. Lu, Synth. Commun., 32, 3455 (2002).

Synthesis and Fungicidal Activities
2087
[4] X. C. Wang, L. Zheng, Z. J. Quang, and D. J. Xu, Synth.Commun., 33, 2891 (2003).
[5] M. Chen and T. Xiao, Chem. Res. Chinese U., 62, 20 (2004).
[6] S. M. El-Khawass and N. S. Habib, J. Heterocylic Chem., 26, 177 (1989).
[7] Q. M. Bano and S. G. Tiwari, Indian J. Chem., 31B, 714 (1992).
[8] F. M . Liu, J. X. Yu, and W. J. Lu, Chin. J. Chem., 17, 62 (1999).
[9] L. X. Zhang, A. J. Zhang, and G. Q. Zhou, Chinese J. Org. Chem., 22, 663 (2002).
[10] M. Li, L. R. Wen, and W. J. Fu, Chinese J. Org. Chem., 23, 678 (2003).
[11] G. Q. Hu, Z. Q. Zhang, and W. L. Huang, Chinese Acta Chim. Sinica., 62, 204 (2004).
[12] B. S. Holla, R. Gonsalves, and S. Shenoy, Il Farmco, 53, 574 (1998).
[13] B. S. Holla, K. N. Poojary, B. S. Rao, and M. K. Shivananda, Eur. J. Med. Chem., 37,
511 (2002).
[14] R. Reid and N. D. Heindel, J. Heterocylic Chem., 13, 925 (1976).
[15] D. J. Li, D. Q. Long, and H. Q. Fu, Synth.Commun., 35, 2495 (2005).