Synthesis, structure and biological activities of [α-(alkylcarbonyl)- 2-(1,2,4-triazol-1-yl)]ethyl-N,N-dialkydithiocarbamate derivatives

Article abstract of DOI:10.1002/jhet.5570430417

Seven 1,2,4-triazole compounds containing the N,N-dialkyldithiocarbamate group were designed and synthesized. Their structures were identified using infrared spectroscopy, element analysis, ¹H NMR spectroscopy and mass spectrometry, and in two cases by single crystal X-ray diffraction. The result of the biological test showed that the seven compounds all have fungicidal and plant growth-regulating activities.

Full text of DOI:10.1002/jhet.5570430417

Jul-Aug 2006
925
Synthesis, Structure and Biological Activities of [ꢀ-(Alkylcarbonyl)-
2-(1,2,4-Triazol-1-yl)]ethyl-N,N-Dialkydithiocarbamate Derivatives
Fangfang Jian,* Hailian Xiao, Chongyi Zhu, Liangzhong Xu
New Materials & Function Coordination Chemistry Laboratory, Qingdao University of Science and Technology,
Qingdao, 266042, P. R. China (* E-mail: ffj2003@163169.net)
Received September 15, 2005
O
C
O
1. HCHO,(CH3)2NH • HCl
N
CH3
R'
R'C CHCH2
Br
N
N
2.
HN
3. NaOAC-HDAC, Br2
O
R2NCS2Na
N
R'
C
CHCH2N
S
R2N
C
S
R=Me, Et
R'=Me3C, Ph, p-Cl-Ph, p-CH3O-Ph
Seven 1,2,4-triazole compounds containing the N,N-dialkyldithiocarbamate group were designed and
synthesized. Their structures were identified using infrared spectroscopy, element analysis, 1H NMR
spectroscopy and mass spectrometry, and in two cases by single crystal X-ray diffraction. The result of the
biological test showed that the seven compounds all have fungicidal and plant growth-regulating activities.
J. Heterocyclic Chem., 43, 925 (2006).
Introduction.
In both compounds 1 and 4, the bond lengths and
angles are generally normal in the triazole ring and N,N-
dimethyldithiocarbamate group [6-8]. The triazole ring
with the conjunction carbon atom are all fairly planar, and
the largest deviation from the least squares plane through
the ring atoms are 0.022 and 0.010 Å for 1 and 4,
respectively. All atoms in N,N-dimethyldithiocarbamate
group in these two compounds are also quite planar, and
the largest deviation from the least squares plane are
0.014 and 0.011 Å for 1 and 4, respectively. The dihedral
angle between the plane of N,N-dimethyldithiocarbamate
group with the plane of triazole moiety are 9.96(2)˚ and
5.29(2)˚ for 1 and 4, respectively.
1,2,4-Triazole and its derivative are one of the most
widely used fungicides in modern society because of
their highly efficient, low toxicity and absorbent
properties [1-3]. At present, the studies on triazole
derivatives are mainly concentrated on compounds with
triazole as the only active group. The report has rarely
been found about triazole compounds containing both
triazole group and other active group in a single molecule.
Dialkylsubstituted dithiocarbamate salts have also shown
interesting biological effects [4]. N,N-Dialkyldithiocar-
bamate is also known as broad-range fungicides have a
different fungicidal mechanism than that of triazole
compounds [5]. Triazole compounds containing the N,N-
dialkyl dithiocarbamate functional group have rarely been
reported. In order to search for new triazole compounds
with higher bioactivity, seven compounds were designed
and synthesized and the biological activities of these
compounds were tested. Also, their structures were
1
determined by IR, elemental analysis, H NMR spectra
and single crystal X-ray diffraction.
Results and Discussion.
The molecular structures of compounds
1
(C12H20N4OS2) and 4 (C15H18N4O2S2) are illustrated in
Figure 1 and 2, respectively. Figure 3 shows a perspective
view of the crystal packing in the unit cell for 4. Selected
bond distances and angles of 1 and 4 are listed in Table 1.
Figure 1 Molecular structure for 1 with the atomic numbering scheme.

926
F. Jian, H. Xiao, C. Zhu, L. Xu
Vol 43
C=O double bond length 1.17 Å [10]. In compound 4,
bond lengths and angles are generally normal in the
phenyl ring [11]. The C(4)-C(5) and C(4)-C(8) bond
lengths of 1.527(4) Å and 1.540(4) Å are also similar to
those of standard C-C single bond length, while C(8)-O(2)
bond length 1.214(4) Å is much longer, which assign to
the electron delocalization effect between phenyl ring and
carbonyl group. The phenyl ring [C(2), C(3), C(4), C(5),
C(6) and C(7)] with the conjunction carbon atom C(8) and
methoxy group [C(1) and O(1)] are fairly planar, plane
equation: 7.1646x- 0.5670y –3.1279z = -0.0305, and the
largest deviation from the least squares plane is 0.042(3)
Å. This plane is nearly perpendicular to the plane of N,N-
dimethyldithiocarbamate group, with the dihedral angle of
89.26(2)˚. The dihedral angle between the triazole ring
moiety and the phenyl ring is 83.97(2)˚.
Figure 2 Molecular structure for 4 with the atomic numbering scheme.
In the crystal lattice of compounds 1 and 4, there are
some potentially weak (C-H···Y hydrogen bonds, Y = O,
N and S) intermolecular interactions [12, 13]. In
compound 1, the N(4) atom with C(10) form weak C-
H···N intermolecular interaction, the donor and acceptor
distances are C(10)···N(4) 3.3635(1) Å. In compound 4,
the O(2) atom with C(6), and N(3) atom with C(7) form
weak C-H···Y intermolecular interactions, the donor and
acceptor distances are C(6)···O(2) of 3.2427 Å and
C(7)···N(3) of 3.3627 Å. The other intermolecular
interactions are due to the two different types of ꢀ bond
interactions: C-H···ꢀ supramolecule interactions and ꢀ-ꢀ
stacking interaction [14, 15]. There are two types of C-
H···ꢀ supramolecule interactions between C-H and
aromatic rings in compound 1. The distances between
C(9)-H(9A) and C(9)-H(9C) to triazole ring are all 3.667
Å, and bond angles are 114.41º and 103.31º, respectively.
In compound 4, there are two different types of ꢀ-ꢀ
stacking interactions, the center-to-center distances
between two adjacent phenyl rings are 3.963 Å and 3.902
Å, respectively. It is obvious that they form the stronger
ꢀ-ꢀ stacking interaction [16]. In the solid state, all above
extension hydrogen and intermolecular interactions
stabilize the structure.
In the IR spectra, the absorption peaks at about 3100 cm-1
attribute to unsaturated =C-H bond stretching vibration, the
absorption peak at 900~650 cm-1 is assigned to the =C-H
outside-plane bending vibration. The C=N stretching
vibrations are found for all compounds at about 1500 cm-1
[17]. The strong band in the range 1660-1700 cm-1 is
attributed to the ꢀC=O stretching vibration, the band in the
range 1130-1200 cm-1 belonging to the ꢀC=S stretching
vibration [18, 19]. We found that the ꢀC=O stretching
vibration band peak for C = O connected to tertiary butyl
group have shifted slightly to higher frequency by about 20-
30 cm-1 compared with that of C = O groups connected with
Figure 3 A view of the crystal packing down the a axis for the
compound 4
Table 1
Selected bond lengths [Å] and angles [º] for compounds 1 and 4.
Compound 1
1.780(2)
Compound 4
1.780(2)ꢀ
S(1)-C(3)
S(1)-C(4)
S(2)-C(3)
N(1)-C(3)
S(1)-C(13)ꢀ
1.810(2)
1.651(2)
1.333(3)
S(1)-C(9)ꢀ
1.813(2)ꢀ
1.659(2)ꢀ
1.332(2)ꢀ
103.2(8)
109.0(2)
131.2(2)
119.8(1)
102.4(2)
S(2)-C(13)ꢀ
N(1)-C(11)ꢀ
C(3)-S(1)-C(4) 103.2(1)
S(2)-C(3)-S(1) 124.1(1)
C(13)-S(1)-C(9)
C(11)-N(1)-N(2)
C(11)-N(1)-(10)
N(2)-N(1)-C(10)
C(12)-N(2)-N(1)
N(1)-C(3)-S(1) 111.6(2)
N(1)-C(3)-S(2) 124.4(2)
C(10)-C(4)-(1)
109.2(2)
In compound 1, the bond lengths and angles in the tert-
butyl group are in good agreement with the earlier report
[9]. The C(4)-C(5) and C(4)-C(10) bond lengths of
1.535(3) Å and 1.525(3) Å are all similar to those of
standard C-C single bond length 1.54 Å, while C(5)-O(1)
bond length 1.205(4) Å is longer than that of standard

Jul-Aug 2006
[ꢀ-(Alkylcarbonyl)-2-(1,2,4-Triazol-1-yl)]ethyl-N,N-Dialkydithiocarbamate Derivatives
927
(4000-400 cm-1), as KBr pellets, were recorded on a Nicolet FT-
IR 170X spectrophotometer. H NMR spectra were measured
aromatic rings. The IR data are in good agreement with the
predicted structure of the target compounds.
1
with a JEOL FX-90Q nuclear magnetic resonance spectrometer
(CDCl3 as solvent, TMS as internal standard). The melting
points were determined on a Yanaco MP-500 melting point
apparatus.
The intermediates N,N-dialkyldithiocarbamate were prepared
according to the literature report [22]. Alkyl N-imadazolepropyl
ketone were prepared according to the literature [23] and [24]. The
synthesis of the intermediate alkyl ꢀ-bromo-ꢁ-N-imadzole-propyl
ketone and the seven target compounds are described below.
To a 100 mL flask 15 mmol of intermediate alkyl N-imadazole-
propyl ketone, 25 mL acetic acid and 15 mmol sodium acetate were
added. Then 15 mmol bromine was dropwise added with stirring at
15 ~ 25 ºC. The reaction was maintained until the mixture turned
colorless or light yellow for about 2 ~ 3 h. Then 50 mL water and
40 mL chloroform were added. The organic layer was successively
washed with saturated sodium bicarbonate solution and brine, then
The 1H NMR data for seven compounds are as
predicted except for two protons on triazole ring. The
chemical shifts for triazole ring protons are affected by R’
group. When R’ is aromatic rings, the chemical shifts for
two protons are at ꢀ = 7.98-8.22. When R’ is Me3C, their
chemical shifts are ꢀ = 8.03 and ꢀ = 7.87.
Compounds 1-7 were screened for their fungicial
activities against P. Zeae, A. Solani, P. Asparagi, P.
Piricola and C. Archidicala at 50 μg/mL concentrations
following the agar plate diffusion method [20, 21] and
compared with triazolone. Compounds 1, 2, 4 and 5 all
exhibit some efficiency on P. Zeae, A. Solani, P.
Asparagi, P. Piricola and C. Archidicala, but not
significantly, the inhibiting rate of compounds 2 and 5 are
Table 2
The fungicidal and plant grown regulator activities of compounds 1-7
Fungicidal activities(c=0.005%,inhibition)
Plant growth regulator activities
Compound
No
Wheat
coleoptile
elongation
Rooting of
cucumber
cotyledon
Rape
hypocotyls
inhibition
P.zeae
A.solani
P.asparagi
P.piricola
C.arachidicala
1
20.0
45.0
30.8
15.5
45.0
10.0
11.5
46.2
35.5
35.5
0
22.6
35.5
12.9
0
28.6
28.6
0
28.6
28.6
0
20.0
24.4
24.6
20.0
24.4
33.3
26.2
64.6
23.5
35.3
0
23.5
35.3
11.8
0
-7.8
-3.9
-17.1
-22.1
-28.7
-3.9
+39.3
+33.8
+1.0
+25.6
+83.0
+14.7
+77.5
+50.2
-5.9
-9.1
-7.7
-12.3
11.9
-5.0
2
3
4
5
6
7
33.3
22.5
-7.0
-24.0
-9.1
-64.2
triazolone
0
0
dried over sodium sulfate and the chloroform solution containing
about 15 mmol of intermediate alkyl ꢀ-bromo-ꢁ-N-imadazole-
propyl ketone was filtrated into a 100 mL flask. Cooled with ice-
water and 30 mL acetone solution of intermediate N,N-dialkyl-
dithiocarbamate (R = Me, Et) was added under stirring and the
mixture was stirred at around 0 ºC for about 1 h. The solution was
filtered, concentrated and purified by flash chromatography (silica
gel, Vethyl ethanoate: Vcyclohexane = 5:1) to afford the seven target
compounds. Single crystals suitable for X-ray measurements of
compounds 1 and 4 were obtained by recrystallization from ethyl
ethanoate at room temperature.
the highest in these compounds and only reach to 24.4 ~
45.0%. The plant growth regulator activities of
compounds 1-7 have also been tested towards wheat
coleoptile elongation, rooting of cucumber cotyledon and
rape hypocotyls inhibition at 10 μg/mL and compared
with triazolone. Compounds 5 and 7 show remarkable
growth-promoting activity of 83.0% and 77.5% on
rooting of cucumber cotyledon. As far as the relation of
structure and activity is concerned, when R’ group is
Me3C, the compounds 1 and 5 have better comprehensive
inhibiting rates than when the R’ is an aryl group. As far as
R is concerned, inhibiting activities of the compounds (R =
Et) are higher than the compounds (R = Me). Meanwhile,
it can be seen from Table 2 that the relationship changes
between structure and activity are not regular.
tert-Butyl ꢀ-S-dimethyldithiocarbamate-ꢁ-imadzole-propyl
ketone (1).
Colorless crystal, yield 39.4%, mp 110-112°C; ir (KBr),
1
3123m (CH), 1696 (CO), 1504 (CN), 1141 (CS). H nmr (300
MHz; CD3Cl; Me4Si): 8.03 (s, 1H,Tr-H), 7.87 (s, 1H, Tr-H),
5.57~5.75 (dd, 1H, SCH, J=4.38 Hz, J=10.12 Hz), 4.59~4.88
(dd, H, CH2, J=10.12Hz, J=13.18 Hz), 4.26~ 4.48 (dd, H,CH2,
J=4.38Hz, J=13.18Hz), 3.59 (s, 3H, N-CH3), 3.34 (s, 3H, N-
CH3), 0.99 (s, 9H, Me3C).
EXPERIMENTAL
All chemical reagents were obtained from a commercial
source and used without further purification. Elemental analyses
were measured with a Perkin-Elmer 1400C analyzer. IR spectra
Anal. Calcd. for C12H20N4OS2: C, 47.97% H, 6.71% N,
18.65%; Found: C, 48.06% H, 6.65% N, 18.61%.

928
F. Jian, H. Xiao, C. Zhu, L. Xu
Vol 43
Phenyl ꢀ-S-dimethyldithiocarbamate-ꢁ-imadzole-propyl ketone
(2).
ꢀ-Methoxyphenyl ꢀ-S-diethyldithiocarbamate-ꢁ-imadzole-
propyl ketone (7).
Colorless crystal, yield 42.9%, mp 99-101°C; ir (KBr), 3116m
(CH), 1676 (CO), 1596 and 1580 (C=C), 1503 (CN), 1135 (CS).
1H nmr (300 MHz; CD3Cl; Me4Si): 8.22 (s, 1H, Tr-H), 8.02 (s,
1H, Tr-H), 3.59 (s, 3H, N-CH3) 3.34 (s, 3H, N-CH3), 4.44~4.67
(dd, H, CH2, J=4.38Hz, J=13.5Hz), 4.86~5.18 (dd, H, CH2,
J=9.48Hz, J=13.5Hz), 6.30~6.48 (dd, 1H, SCH, J=4.38Hz,
J=9.18Hz), 7.27~8.03 (m, 5H, Ph). Ms: m/z 321 (MH+), 251
Colorless crystal, yield 36.4%, mp 99-100°C; ir (KBr), 3124m
(CH), 1673 (CO), 1597 (C=C), 1490 (CN), 1205 (CS). H nmr
1
(300 MHz; CD3Cl; Me4Si): 8.14 (s, 1H, Tr-H), 7.98 (s, 1H, Tr-
H), 1.17~1.31 (t, 6H, 2CH3), 6.24~8.00 (m, 4H, Ph), 3.62~4.15
(m, 4H, 2N-CH2), 4.44~4.63 (dd, H, CH2, J=4.50Hz,
J=13.76Hz), 4.80~5.08 (dd, H, CH2, J=9.23Hz, J=13.76Hz),
6.24~6.41 (dd, 1H, SCH, J=4.50Hz, J=9.20Hz). Ms: m/z 379
+
+
+
(MH+), 309 [(CH3OPhCO(CH2)CH2 S2N(CH3CH2)2)], 230
[(PhCO(CH2)CH2 S2N(CH3)2)], 200 (PhCOCH2 CH2Im), 131
(PhCOCH2 CH2), 105 (PhCOH+), 77 (PhH+).
+
+
+
(CH3OPhCOCH2 CH2Im), 162 (CH3OPhCOCH2 CH2).
Anal. Calcd. for C17H22N4O2S2: C, 53.94% H, 5.86% N,
14.08%; Found: C, 54.01% H, 5.83% N, 14.01%.
Anal. Calcd. for C14H16N4OS2: C, 52.48% H, 5.03% N,
17.40%; Found: C, 52.70% H, 4.99% N, 17.29%.
ꢀ-Chlorophenyl ꢀ-S-dimethyldithiocarbamate-ꢁ-imadzole-propyl
ketone (3).
X-ray Structure Determination.
In the determination of the structure of the single crystal, X-
ray intensities were recorded by Rigaku Raxis-IV diffractometer
using Mo-Kꢀ radiation (ꢁ
Colorless crystal, yield 53.5%, mp 92-93°C; ir (KBr), 3129m
1
(CH), 1681 (CO), 1590 (C=C),1504 (CN), 1141 (CS). H nmr
=
0.71073 Å) graphite
(300 MHz; CD3Cl; Me4Si): 8.18 (s, 1H, Tr-H), 7.94 (s, 1H, Tr-
H), 3.56 (s, 3H, N-CH3), 3.32 (s, 3H, N-CH3), 4.57~4.78 (dd, H,
CH2, J=4.40Hz, J=13.46Hz), 4.82~ 4.93 (dd, H, CH2, J=9.30Hz,
J=13.46Hz), 6.26~6.38 (dd, 1H, SCH, J=4.14Hz, J=9.25Hz),
7.26~7.97 (m, 4H, Ph)
Anal. Calcd. for C14H15ClN4OS2: C, 47.38% H, 4.26% N,
15.79%; Found: C, 47.51% H,4.21% N, 15.80%.
monochromator. The structure was solved by direct methods
using SHELXS-97 program [25]. All the non-hydrogen atoms
were refined on F2 anisotropically by full-matrix least squares
method. Hydrogen atoms were located from the difference
Fourier map and added to the structure calculations, but their
positions were not refined. The contributions of these hydrogen
atoms were included in structure-factor calculations. The
summaries of the key crystallographic information for
compounds 1 and 4 are given in Table 3.
ꢀ-Methoxyphenyl ꢀ-S-dimethyldithiocarbamate-ꢁ-imadzole-
propyl ketone (4).
Colorless crystal, yield 73.3%, mp 120-122°C; ir (KBr),
3138m (CH), 1666 (CO), 1302 (C=C),1505 (CN), 1138 (CS). 1H
nmr (300 MHz; CD3Cl; Me4Si): 8.15 (s, 1H, Tr-H), 7.98 (s, 1H,
Tr-H), 3.55 (s, 3H, N-CH3), 3.32 (s, 3H, N-CH3), 4.56~4.79 (dd,
H, CH2, J=4.36Hz, J=12.92Hz), 4.82~4.93 (dd, H, CH2,
J=9.30Hz, J=12.92Hz), 6.21~6.33 (dd, 1H, SCH, J=4.36Hz,
J=9.23Hz), 6.81~8.00 (m, 4H, Ph), 3.82 (s, 3H, MeO)
Table 3
Crystallographic details for compounds 1 and 4
Empirical formula C12H20N4OS2 1
C15H18N4O2S2 4
350.45
Formula weight
Crystal system,
space group
Unit cell
300.44
Triclinic, Pꢀ
a = 7.348(2) Å
Monoclinic, P21/c
Anal. Calcd. for C15H18N4O2S2: C, 51.41% H, 5.18% N,
15.99%; Found: C, 51.17% H, 5.16% N, 16.30%.
dimensions
a = 12.315(3) Å ꢀ= 90º ꢀ=90.32(3)º
tert-Butyl ꢀ-S-diethyldithiocarbamate-ꢁ-imadzole-propyl ketone
(5).
b = 12.057(2) Å ꢁ=
118.55(3)º
b = 11.051(2) Å
ꢁ=101.97(3)º
c = 11.209(2) Å
ꢂ=105.13(3)º
857.8(3) Å3
2, 1.357
Colorless crystal, yield 23.1%, mp 65-66°C; ir (KBr), 3124m
c = 12.532(3) Å ꢂ= 90º
1634.5(6) Å3
4, 1.221
1
(CH), 1700 (CO), 1502 (CN), 1205 (CS). H nmr (300 MHz;
Volume
CD3Cl; Me4Si): 8.05 (s, 1H, Tr-H), 7.88 (s, 1H, Tr-H),
1.18~1.36 (t, 6H, 2CH3), 0.97 (s, 9H, Me3), 3.67~4.00 (m, 4H,
2N-CH2), 4.34~4.51 (dd, H, CH2, J=4.33Hz, J= 12.98Hz),
4.60~5.01 (dd, H, CH2, J=10.02Hz, J= 12.98Hz), 5.62~5.75 (dd,
1H, SCH, J=4.33Hz, J=10.02Hz)
Z, Dc (Mg/m3)
F(000)
640
368
ꢁ range
1.88 to 27.53°
-15ꢁh0ꢁ, -5ꢁkꢁ15, -
13ꢁlꢁ16
1.86 to 27.53°
-9ꢁhꢁ9, 0ꢁkꢁ14, -
14ꢁlꢁ14
2877 /2877 [Rint=
0.0000]
Limiting indices
Reflections
Anal. Calcd. for C14H24N4OS2: C, 50.19% H, 7.36% N,
17.06%; Found: C, 50.13% H, 7.32% N, 17.01%.
5132 / 3130 [Rint
=
collected / unique 0.0248]
ꢂ
GOF
max = 27.51°
82.8 %
1.017
72.7 %
1.031
Phenyl ꢀ-S-diethyldithiocarbamate-ꢁ-imadzole-propyl ketone (6).
Colorless crystal, yield 29.6%, mp 102-103°C; ir (KBr),
3118m (CH), 1678 (CO), 1594 and 1580 (C=C), 1497 (CN),
1203 (CS). H nmr (300 MHz; CD3Cl; Me4Si): 8.17 (s, 1H, Tr-
H), 8.01 (s, 1H, Tr-H), 1.26~1.80 (t, 6H, 2CH3), 7.24~8.02 (m,
5H, Ph), 3.62~4.05 (m, 4H, 2N-CH2), 4.50~4.66 (dd, H, CH2,
J=4.43Hz, J=13.10Hz), 4.82~5.10 (dd, H, CH2, J=9.28Hz,
J=13.10Hz), 6.31~6.48 (dd, 1H, SCH, J=4.43Hz, J=9.12Hz).
Anal. Calcd. for C16H20N4OS2: C, 55.14% H, 5.78% N,
16.08%; Found: C, 55.09% H,5.74% N, 16.20%.
Final R indices
[I>2ꢃ(I)]
R1 = 0.0449,
wR2 = 0.1043
R1 = 0.0552,
wR2 = 0.1384
0.319 and -0.334 e·Å-3
1
Largest diff. peak 0.235 and -0.191 e·Å-3
and hole
Acknowledgments
This work was supported by the Natural Science Foundation
of Shandong Province (No.Y2005B04).

Jul-Aug 2006
[ꢀ-(Alkylcarbonyl)-2-(1,2,4-Triazol-1-yl)]ethyl-N,N-Dialkydithiocarbamate Derivatives
929
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