Synthesis and antifungal activities of ω-[4-aryl-5-(1-phenyl-5-methyl-1,2,3-triazol-4-yl)-1,2,4-triazol-3-thio]- ω-(1H-1,2,4-triazol-1-yl)acetophenones

Article abstract of DOI:10.1002/jccs.200100022

New 4-aryl-5-(1-phenyl-5-methyl-1,2,3-triazol-4-yl)-1,2,4-triazol-3-thiones 3 have been synthesized by the intramolecular cyclization of 4-aryl-1-(1-phenyl-5-methyl-1,2,4-triazol-4-formyl)thiosemicarbazides 2 with an 8% NaOH solution, and then 3 reacted w

Full text of DOI:10.1002/jccs.200100022

JournaloftheChineseChemicalSociety, 2001, 48, 121-125
121
Synthesis and Antifungal Activities of -[4-Aryl-5-(1-phenyl-5-methyl-1,2,3-
triazol-4-yl)-1,2,4-triazol-3-thio]- -(1H-1,2,4-triazol-1-yl)acetophenones
a
Chang-Hu Chua ( 褚長虎 ), Xin-Ping Huia (
Zi-Yi Zhang*a ( 張自義 ), Zhi-Chun Lib (
), Yan Zhang (
),
惠新平
張艷
) and Ren-An Liaob (
)
李之春
aDepartmentofChemistry,NationalLaboratoryofAppliedOrganicChemistry,
Lanzhou Uni ver sity, Lanzhou 730000, P. R. China
廖仁安
bStateKeyLaboratoryofElemento-OrganicChemistry,NankaiUniversity,Tianjin300071,P.R. China
New 4-aryl-5-(1-phenyl-5-methyl-1,2,3-triazol-4-yl)-1,2,4-triazol-3-thiones 3 havebeensynthesizedby
the intramolecular cyclization of 4-aryl-1-(1-phenyl-5-methyl-1,2,4-triazol-4-formyl)thiosemicarbazides 2
with an 8% NaOH so lu tion, and then 3 re acted with -bromo- -(1H-1,2,4-triazol-1-yl)acetophenone to af-
ford -[4-aryl-5-(1-phenyl-5-methyl-1,2,3-triazol-4-yl)-1,2,4-triazol-3-thio]- -(1H-1,2,4-triazol-1-yl)-
acetophenones4.Thepreliminarybiologicaltestshowedthattherepresentativecompoundspossesssome
antifungalactivities.
INTRODUCTION
1H-1,2,4-triazole de riv a tives have been re ported to as-
hydrazine with aryl isothiocyanates re sulted in the for ma tion
of 4-aryl-1-(1-phenyl-5-methyl-1,2,3-triazol-4-formyl) thio-
semicarbazides 2. The thiosemicarbazides could be cyclized
in8%sodiumhydroxidesolutiontoform4-aryl-5-(1-phenyl-
5-methyl-1,2,3-triazol-4-yl)-1,2,4-triazol-3-thiones 3. Then,
treat ment of3 with -bromo- -(1H-1,2,4-triazol-1-yl)aceto-
phenone in anhydrous acetone will give -[4-aryl-5-(1-
phenyl-5-methyl-1,2,3-triazol-4-yl)-1,2,4-triazol-3-thio]-
-(1H-1,2,4-triazol-1-yl)acetophenones 4.
so ci ate with fun gi cidal, anti-inflammatory, antiparasitic, in-
secticidal,herbicidal,antiviral,antitumor,hypotensiveef-
fectsandplantgrowthregulatoryactivities.1-7 Up till now, a
great num ber of these com pounds have been syn the sized,
among which some com mer cially pes ti cides have been de-
vel oped in clud ing triadimenfon, triadibenol and dinicon-
azole. Moreover, much attention has been paid to acyl-
thiosemicarbazides and those compounds bearing 1,2,3-
triazole and sub sti tuted 1,2,4-triazole moi eties due to their
significantbiologicalactivities,suchasantifungal,herbi-
cidal, anti-inflammatory, in sec ti cidal and plant growth reg u-
latoryactivities.8-17 In view of these ob ser va tions and our
continuedinterestsinthesynthesisofbiologicallyactive
heterocyclic com pounds, it was worth while to syn the size
new polyheterocyclic com pounds which pos sess a 1H-1,2,4-
triazolering,substituted1,2,4-triazoleringand1,2,3-triazole
moietybecausethebiologicalactivitiesmaybeimproved
manytimesoverthantheirparentsbyincorporatingeverybi-
o log i cally ac tive group with the microstructure of the cell.
Herein, we wish to de scribe the syn the sis of new acyl thio-
semicarbazides, sub sti tuted 1,2,4-triazoles and 1H-1,2,4-
triazolederivativescontaining1,2,3-triazolenuclei.
Scheme I
O
O
S
N
NH
CNHNH2
CNHNHCNHAr
N
N
N
N
N
N
N
S
N
Me
N
Ar
EtOH
Me
NaOH
8%
N
Me
+ ArN=C=S
3
2
1
O
N
N
S
O
N
N
N
Br
N
N
Ar
Me
N
N
N
N
+
N
3
4
The struc tures of the com pounds syn the sized were es-
tab lished on el e men tal anal y ses and spec tral data. The IR
spec tra of com pounds 2 showed two char ac ter is tic peaks in
the range of 1657-1677 cm-1 and 1576-1585 cm -1 due to C=O
and C=N groups, re spec tively. The1H NMR spec tra of2 dis-
played singlets for NH pro tons at 10.52-10.71 ppm and
9.61-10.04 ppm, re spec tively. The methyl pro tons in the
1,2,3-triazole ring dis played a sin glet at 2.54-2.64 ppm.
Though the ar o matic com pounds usu ally have a strong mo-
RESULTSANDDISCUSSION
The re ac tion se quence for ti tle com pounds is out lined
in Scheme I. The con den sa tion of the heterocyclic formyl-

122 J. Chin. Chem. Soc., Vol. 48, No. 1, 2001
Chu et al.
lecularionpeak(EI),themolecularionpeaksof2 are weak or
not ob served ow ing to the C-N bond be tween N2H and -C-
eas ily break ing (Scheme II). For ex am ple, com pound2f ex-
hib its strong frag ment peaks at m/z 217 (40), 215 (100) and
213 (96), and its mo lec u lar ion peak was not ob served. The
1H NMR spectra of 3 showed singlets at 14.1 ppm and
around 2.5 ppm, which were as signed for the pro tons of NH
and methyl groups, re spec tively. The mo lec u lar ion peaks of
3 are all strong. The IR spec tra of4 showed two strong bands
in the range of 1688-1699 cm-1 and 1598-1594 cm-1 areattrib-
Scheme II
O
O
S
C
CNHNH2
+
.
N
N
+
.
CNHNH
Four member ring
rearrangement
3
N
N
+
.
2
1
or
ArN=C=S
H
N
Ar
N
Me
4
N
Me
While their methyl pro tons in the 1,2,3-triazole ring dis-
played a sin glet at 2.79-2.68 ppm. By an a lyz ing the mass
spectraof 4, it was found that the mo lec u lar ion peaks were
very weak prob a bly due to their polyheterocyclic struc ture.
Therepresentativecompounds2a, 2j, 2k, 2l, 3a, 3b,
1
uted to C=O and C=N groups, re spec tively. Their H NMR
spec tra dis played two singlets for the 1H-1,2,4-triazole pro-
tons at 9.30-9.06 ppm and 9.00-8.40 ppm, re spec tively.
Table 1. Yields, Melting Points, Formulas and Elemental Analyses for Compounds 2, 3 and 4
Found (required) (%)
H
Yield
(%)
M.p.
(oC)
Compd.
Ar
Formula
C
N
2a
2b
2c
2d
2e
2f
2g
2h
2i
C6H5
81
79
85
86
83
85
88
75
90
85
84
87
81
90
89
87
85
80
78
82
85
88
90
82
87
85
91
89
92
82
90
78
80
90
80
128-9
139-40
166-7
190-2
135-6
147-8
201-2
160-1
137-8
184-5
176-7
168-9
216-7
221-2
206-7
226-7
175-6
254-5
242-4
246-8
219-20
248-9
262-4
233-4
175-6
136-7
154-5
200-1
228-9
173-4
198-9
218-9
183-4
229-30
161-2
C17H16N6OS
C18H18N6OS
C18H18N6OS
C17H15ClN6OS
C17H15BrN6OS
C17H15BrN6OS
C17H15BrN6OS
C18H18N6O2S
C18H18N6O2S
C17H15ClN6OS
C18H15F3N6OS
C17H14Cl2N6OS
C17H14N6S
57.99 (57.94)
59.39 (59.00)
59.37 (59.00)
52.82 (52.78)
47.06 (47.34)
47.62 (47.34)
47.04 (47.34)
56.76 (56.53)
56.48 (56.53)
52.58 (52.78)
51.61 (51.43)
48.49 (48.46)
61.20 (61.06)
58.93 (59.00)
62.20 (62.05)
55.40 (55.36)
49.20 (49.41)
49.35 (49.41)
49.18 (49.41)
59.38 (59.33)
59.52 (59.33)
55.71 (55.36)
53.49 (53.73)
50.39 (50.63)
62.09 (62.41)
63.00 (63.03)
62.81 (63.03)
58.36 (58.53)
53.94 (54.19)
54.28 (54.19)
53.98 (54.19)
60.75 (61.19)
60.76 (61.19)
58.28 (58.53)
57.22 (57.23)
5.04 (4.68)
5.06 (4.95)
5.31 (4.95)
3.57 (3.91)
3.77 (3.50)
3.68 (3.50)
3.45 (3.50)
4.78 (4.74)
4.68 (4.74)
4.21 (3.91)
3.55 (3.60)
3.40 (3.35)
4.27 (4.22)
5.10 (4.95)
4.76 (4.63)
3.53 (3.52)
3.26 (3.17)
3.44 (3.17)
3.27 (3.17)
3.90 (4.42)
4.26 (4.42)
3.53 (3.52)
3.42 (3.26)
3.01 (3.00)
4.42 (4.07)
4.58 (4.34)
4.16 (4.34)
3.44 (3.64)
3.30 (3.37)
3.17 (3.37)
3.04 (3.37)
4.01 (4.22)
4.05 (4.22)
3.60 (3.64)
3.59 (3.43)
23.58 (23.85)
22.53 (22.93)
22.72 (22.93)
21.39 (21.72)
19.29 (19.69)
19.32 (19.69)
19.65 (19.69)
22.32 (21.93)
22.12 (21.93)
21.50 (21.72)
19.58 (19.99)
19.76 (19.95)
25.13 (25.13)
22.82 (22.93)
24.22 (24.12)
23.05 (22.78)
20.54 (20.33)
20.36 (20.33)
20.61 (20.33)
22.85 (23.06)
23.26 (23.06)
22.37 (22.78)
21.10 (20.86)
21.18 (20.84)
23.92 (24.26)
23.47 (23.62)
23.64 (23.62)
22.66 (22.75)
20.83 (21.06)
20.83 (21.06)
20.80 (21.06)
22.66 (22.94)
22.57 (22.94)
22.60 (22.75)
20.92 (21.45)
p-CH3C6H4
o-CH3C6H4
m-ClC6H4
p-BrC6H4
o-BrC6H4
m-BrC6H4
o-CH3OC6H4
p-CH3OC6H4
p-ClC6H4
m-CF3C6H4
2,4-Cl2C6H3
C6H5
p-CH3C6H4
o-CH3C6H4
m-ClC6H4
p-BrC6H4
2j
2k
2l
3a
3b
3c
3d
3e
3f
3g
3h
3i
C18H16N6S.H2O
C18H16N6S
C17H13ClN6S
C17H13BrN6S
C17H13BrN6S
C17H13BrN6S
C18H16N6OS
C18H16N6OS
C17H13ClN6S
C18H13F3N6S
C17H12Cl2N6S
C27H22N9OS
C28H23N9OS
C28H23N9OS
C27H21ClN9OS
C27H21BrN9OS
C27H21BrN9OS
C27H21BrN9OS
C28H24N9O2S
C28H24N9O2S
C27H21ClN9OS
C28H21F3N9 OS
o-BrC6H4
m-BrC6H4
o-CH3OC6H4
p-CH3OC6H4
p-ClC6H4
m-CF3C6H4
2,4-Cl2C6H3
C6H5
p-CH3C6H4
o-CH3C6H4
m-ClC6H4
p-BrC6H4
3j
3k
3l
4a
4b
4c
4d
4e
4f
4g
4h
4i
o-BrC6H4
m-BrC6H4
o-CH3OC6H4
p-CH3OC6H4
p-ClC6H4
4j
4k
m-CF3C6H4

-[4-Aryl-5-(1-phenyl-5-methyl-1,2,3-triazol-4-yl)-1,2,4-triazol-
J. Chin. Chem. Soc., Vol. 48, No. 1, 2001 123
3-thio]- -(1H-1,2,4-triazol-1-yl)acetophenones
Table 2. 1H NMR Spectral Data for Compounds 2, 3 and 4
No.
1H NMR (CDCl3 or DMSO-d6 ppm)
2a
2b
10.56 (s, 1H, NH), 9.76 (s, 2H, 2NH), 7.96~7.12 (m, 10H, ArH), 2.60 (s, 3H, CH3)
10.51 (s, 1H, NH), 9.65 (s, 2H, 2NH), 7.64 (s, 5H, ArH), 7.36 (d, 2H, J = 8.8 Hz, ArH), 7.11 (d, 2H, J = 8.8
Hz, ArH), 2.55 (s, 3H, CH3), 2.28 (s, 3H, CH3)
2c
2d
2e
2f
2g
2h
2i
10.56 (s, 1H, NH), 9.68 (s, 2H, 2NH), 8.16~7.20 (m, 9H, ArH), 2.58 (s, 3H, CH3), 2.24 (s, 3H, CH3)
10.58 (s, 1H, NH), 9.96 (s, 2H, 2NH), 7.68~7.12 (m, 9H, ArH), 2.64 (s, 3H, CH3)
10.64 (s, 1H, NH), 9.90 (s, 2H, 2NH), 7.70~7.56 (m, 9H, ArH), 2.64 (s, 3H, CH3)
10.66 (s, 1H, NH), 10.00 (s, 2H, 2NH), 7.82~7.04 (m, 9H, ArH), 2.58 (s, 3H, CH3)
10.60 (s, 1H, NH), 9.96 (s, 2H, 2NH), 7.88~7.24 (m, 9H, ArH), 2.54 (s, 3H, CH3)
10.71 (s, 1H, NH), 9.88 (s, 2H, 2NH), 8.32~6.88 (m, 9H, ArH), 3.76 (s, 3H, CH3O) 2.56 (s, 3H, CH3)
10.50 (s, 1H, NH), 9.65 (s, 2H, 2NH), 7.64 (s, 5H, ArH), 7.33 (d, 2H, J = 8.8 Hz, ArH), 6.78 (d, 2H, J = 8.8,
ArH), 3.74 (s, 3H, OCH3), 2.55 (s, 3H, CH3)
2j
2k
2l
3a
3b
3c
3d
3e
3f
10.52 (s, 1H, NH), 9.84 (s, 2H, 2NH), 7.60~7.22 (m, 9H, ArH), 2.56 (s, 3H, CH3)
10.64 (s, 1H, NH), 9.98 (s, 2H, 2NH), 8.24~7.44 (m, 9H, ArH), 2.59 (s, 3H, CH3)
10.68 (s,1H, NH), 10.04 (s, 2H, NH), 8.60~8.28 (m, 8H, ArH), 2.56 (s, 3H, CH3)
7.64~7.31 (m, 10H, ArH), 2.50 (s, 3H, CH3)
7.64~7.30 (m, 9H, ArH), 2.48 (s, 3H, CH3), 2.22 (s, 3H, CH3)
7.62~7.22 (m, 9H, ArH), 2.60 (s, 3H, CH3), 2.15 (s, 3H, CH3)
7.65~7.20 (m, 9H, ArH), 2.68 (s, 3H, CH3)
7.68~7.20 (m, 9H, ArH), 2.64 (s, 3H, CH3)
7.76~7.33 (m, 9H, ArH), 2.60 (s, 3H, CH3)
3g
3h
3i
7.84~7.40 (m, 9H, ArH), 2.59 (s, 3H, CH3)
7.79~7.04 (m, 9H, ArH), 3.75 (s, 3H, CH3O), 2.57 (s, 3H, CH3)
7.64~7.00 (m, 9H, ArH), 3.87 (s, 3H, CH3O), 2.52 (s, 3H, CH3)
3j
7.68~7.14 (m, 9H, ArH), 2.57 (s, 3H, CH3)
3k
3l
14.14 (s, 1H, NH), 7.76~7.52 (m, 9H, ArH), 2.53 (s, 3H, CH3)
7.62~7.30 (m, 8H, ArH), 2.62 (s, 3H, CH3)
4a
4b
4c
4d
4e
4f
4g
4h
4i
9.22 (s, 1H, TrH), 8.72 (s, 1H, TrH), 8.08~7.48 (m, 16H, CHTr, ArH), 2.68 (s, 3H, CH3)
9.06 (s, 1H, TrH), 8.52 (s, 1H, TrH), 8.13~7.16 (m, 15H, CHTr, ArH), 2.71 (s, 3H, CH3), 2.20 (s, 3H, CH3)
8.92 (s, 1H, TrH), 8.44 (s, 1H, TrH), 8.06~7.28 (m, 15H, CHTr, ArH), 2.72 (s, 3H, CH3), 2.15 (s, 3H, CH3)
9.08 (s, 1H, TrH), 8.48 (s, 1H, TrH), 8.12~7.52 (m, 15H, CHTr, ArH), 2.70 (s, 3H, CH3)
9.08 (s, 1H, TrH), 8.46 (s, 1H, TrH), 8.14~7.20 (m, 15H, CHTr, ArH), 2.73 (s, 3H, CH3)
9.03 (s, 1H, TrH), 8.65 (s, 1H, TrH), 8.19~7.40 (m, 15H, CHTr, ArH), 2.79 (s, 3H, CH3)
9.04 (s, 1H, TrH), 8.28 (s, 1H, TrH), 8.10~7.28 (m, 15H, CHTr, ArH), 2.68 (s, 3H, CH3)
9.18 (s, 1H, TrH), 8.97 (s, 1H, TrH), 8.12~7.02 (m, 15H, CHTr, ArH), 3.78 (s, 3H, CH3O), 2.70 (s, 3H, CH3)
9.30 (s, 1H, TrH), 9.00 (s, 1H, TrH), 8.12~7.06 (m, 15H, CHTr, ArH), 3.88 (s, 3H, CH3O), 2.68 (s, 3H, CH3)
9.02 (s, 1H, TrH), 8.40 (s, 1H, TrH), 8.12~7.52 (m, 15H, CHTr, ArH), 2.73 (s, 3H, CH3)
9.24 (s, 1H, TrH), 8.64 (s, 1H, TrH), 8.12~7.40 (m, 15H, CHTr, ArH), 2.78 (s, 3H, CH3)
4j
4k
3k, 3l, 4a, 4b, 4e and 4j were screened for their antifungal ac-
tivityapplyingtheagardiffusionmethod. Thepreliminary
resultsindicatedthatthecompoundssynthesizedexhibited
moderateinhibitoryactivityagainstplantpathogeneticfungi
such as cucumber grey mold, rape sclerotium, wheat
gibberella, early blight of to mato, ap ple black rotand cotton
damping-off at a 50 g/mLconcentration.Theinhibitingrate
rangedfrom7.2to68.1%. Moreover, theinhibitingeffectsof
com pounds4 are higher than com pounds 2 and 3. From these
re sults, we can find that the antifungal ac tiv ity im proved
when a 1 H-1,2,4-triazole ring was in cor po rated into a hetero-
cyclicparent.Furtherstudiesonbiologicalactivitiesof 4 are
still in prog ress.
EXPERIMENTAL SECTION
The melt ing points were de ter mined on a Kolfler melt-
ingpointapparatusandwereuncorrected. Elementalanaly-
ses were car ried out on a YanacoCHNCorderMT-3analyzer.
IR spec tra were ob tained in KBr discs on a Nicolet FT-IR
170SX spectrophotometer. Mass spec tra were per formed on
a HP-5988A spec trom e ter (EI at 70 eV). 1H NMR spec tra
(DMSO-d6 or CDCl3) were re corded on a JEOL FX-90X in-
strumentwithTMSasaninternalstandard.
-Bromo- -(1H-1,2,4-triazol-1-yl)acetophenone and
1-aryl-5-methyl-1,2,3-triazol-4-formyl hydrazine were pre-
paredaccordingtotheliteraturemethods,18-19 respectively.

124 J. Chin. Chem. Soc., Vol. 48, No. 1, 2001
Chu et al.
General procedure for prep a ra tion of 4-aryl-1-(1-phenyl-
5-methyl-1,2,3-triazol-4-formyl)thiosemicarbazides 2a-l
A mix ture of 1-phenyl-5-methyl-1,2,3-triazol-4-formyl
hydrazides (5 mmole) and aryl isothiocyanate (5 mmole) in
ethanol(30mL)wasstirredatroomtemperature.After4-5h,
the resulting precipitate was collected by filtration and
recrystallized from DMF-ethanol to af ford 2a-l.
triazol-1-yl)acetophenone (2 mmole) in 20 mL ab so lute ac e-
tone. The mix ture was stirred at room tem per a ture for 5-6 h
and the sol vent was evap o rated. The crude prod ucts were
chromatographedonsilicagelusingpetroleum/acetone(4:1)
aseluent. Afinalrecrystallizationfrom95%ethanolafforded
pure 4a-k.
General procedure for prep a ra tion of 4-aryl-5-(1-phenyl-
5-methyl-1,2,3-triazol-4-yl)-1,2,4-triazol-3-thiones 3a-l
2 (3 mmole) was dis solved in an 8% so dium hy drox ide
so lu tion (40 mL) and the mix ture was refluxed for 5-6 h. It
was cooled, di luted with wa ter and acid i fied with cold aque-
ousHCl.Theresultingprecipitatewascollectedbyfiltration,
washed well with wa ter and recrystallized from 95% eth a nol
to give 3.
ACKNOWLEDGEMENT
Fi nan cial sup port from the State Key Lab o ra tory of
Elemento-Organic Chem is try of Nankai Uni ver sity is grate-
fullyacknowledged.
Received April 12, 2000.
General procedure for preparationof -[4-aryl-5-(1-
phenyl-5-methyl-1,2,3-triazol-4-yl)-1,2,4-triazol-3-thio]- -
(1H-1,2,4-triazol-1-yl)acetophenones 4a-k
Key Words
1H-1,2,4-Triazole; 1,2,3-Triazole;
Thiosemicarbazide; Antifungal activity.
A so lu tion of3 (2 mmole) in 20 mL ab so lute ac e tone
was added dropwise to a so lu tion of -bromo- -(1H-1,2,4-
REFERENCES
Table 3. MS Spectral Data of Compounds 2, 3 and 4
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No.
MS (EI 70 eV)
2f
218 (5), 217 (40), 215 (100), 173 (33), 171 (40), 160 (21),
155 (15), 118 (32), 77 (50)
2l
420 (M+, 3), 368 (5), 259 (19), 217 (20), 203 (100), 161
(30), 145 (55), 118 (20), 77 (38)
3d
3f
368 (M+, 100), 339 (20), 267 (14), 229 (39), 184 (11),
130 (20), 129 (14), 111 (15)
412 (M+, 3), 368 (5), 333 (71), 155 (18), 149 (100), 111
(3), 105 (9), 77 (39)
4b
4g
4j
533 (M+, 5), 505 (6), 428 (5), 348 (36), 319 (29), 304
(24), 288 (15), 187 (4), 105 (100)
5. Elbe, H. L.; Buechel, K. H.; Brandes, W.; Dutzmann, S.;
Luerssen, K. Ger Offen 4,803,833 (Chem Abstr: 1996,
124, 261076).
414 (1), 411 (1), 354 (4), 285 (1), 197 (2), 187 (1), 155
(8), 118 (5), 105 (69), 77 (100)
380 (1), 368 (1), 308 (6), 246 (2), 204 (4), 187 (1), 176
6. Wolfgan, B.; Wolfgan, R.; Arbold, P.; Bartel, S. Ger
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Abstr: 1998, 129, 260464).
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(2), 155 (7), 105 (68), 77 (100)
Table 4. IR (KBr, cm-1) Data of 2 and 4
No.
C=O
C=N
No.
C=O
C=N
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403.
2a
2f
2l
4a
4b
4c
4d
1648
1677
1657
1690
1699
1693
1690
1589
1576
1585
1597
1597
1598
1598
4e
4f
4g
4h
4I
4j
1693
1688
1691
1690
1695
1694
1692
1597
1598
1594
1598
1595
1597
1598
10. Biagi, G.; Dell’ Omoderme, G.; Ferreti, M.; Giorgi, I.;
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