Facile three-component synthesis of dithiocarbamate derivatives with potent antimicrobial activity

Article abstract of DOI:10.3184/030823409X12594282884215

A one-pot three-component synthesis of 3-oxo-3-(phenoxathiin-2-yl)-1- phenyl/(4-chlorophenyl)propyl alkyl/aryldithiocarbamate was achieved from the reaction of 3-phenyl/(4-chlorophenyl)-1-(phenoxathiin-2-yl)propenones, amine and carbon disulfide. The anti

Full text of DOI:10.3184/030823409X12594282884215

JOURNAL OF CHEMICAL RESEARCH 2009
DECEMBER, 753–755
RESEARCH PAPER 753
Facile three-component synthesis of dithiocarbamate derivatives with
potent antimicrobial activity
Mohamed S. Behalo* and Aly A. Aly
Chemistry Department, Faculty of Science, Benha University, PO Box 13518 Egypt
A one-pot three-component synthesis of 3-oxo-3-(phenoxathiin-2-yl)-1-phenyl/(4-chlorophenyl)propyl alkyl/aryl-
dithiocarbamate was achieved from the reaction of 3-phenyl/(4-chlorophenyl)-1-(phenoxathiin-2-yl)propenones,
amine and carbon disulfide. The antimicrobial activities of some compounds were also screened against some
selected bacteria and fungi.
Keywords: dithiocarbamates, phenoxathiin, antimicrobial activity
The chemistry of dithiocarbamates has attracted the
interest of many researchers in the last years. There are
few general approaches involving amines, carbon disulfide
and alkyl halide, epoxide or Michael acceptors to afford
reaction of 2-acetylphenoxathiin and benzaldehyde and
4-chlorobenzaldehyde.23
The reaction of 3-phenyl-1-(phenoxathiin-2-yl)propenone
(1a) (1 mmole), carbon disulfide (3 mmole) and propylamine
(2a) (1.5 mmole) in THF at room temperature afforded 3-oxo-
3-(phenoxathiin-2-yl)-1-phenylpropyl propyldithiocarbamate
(3a) in good yield, Scheme 1. The structure of compound
3a was assigned on the basis of the elemental analysis and
spectroscopic data (1H NMR, 13C NMR, MS and IR).
From these results and in order to generalise this three
components synthesis, chalcones 1a,b were allowed to react
with different amines viz. benzylamine, cyclohexylamine,
1-amino-2-acetaldahyde diethylacetal, diethylamine and
carbon disulfide under the same reaction conditions, it
was found that the reaction afforded the corresponding
dithiocarbamate derivatives 3a–n, Scheme 2. The spectral
data and the elemental analysis of the products are all
consistent with the assigned structures.
The reaction was also carried out in different organic
solvents such as ethanol, acetonitrile, dimethylformamide,
diethyl ether and finally solvent free condition. In these
solvents, the reaction proceeded from low to high yield to
give the corresponding dithiocarbamates.
On the other hand, aromatic amines such as aniline and
p-tolidine did not participate well in the reaction due to
isolation of low yield.
dithiocarbamates1-6 which have demonstrated
a broad
spectrum of applications including agrochemical, medicinal,
and rubber industry.7-10
On the other hand, phenoxathiin derivatives were found to
be active as potential antihypertensive,11 antimicrobial,12,13
antitumour14 and anti-inflammatory agents15 and have
promising fluorescent properties.16,17 Several phenoxathiin
pyridinium derivatives were prepared and acted as effective
antifungal agents against Aspergillus and Candida.18
In previous work, we reported three components synthesis
of dithiocarbamates and heterocycles from azoalkene systems,
carbon disulfide and primary amine.19 In our ongoing
research programme aimed at the synthesis of biologically
active compounds,20-22 we now report one pot synthesis
of dithiocarbamates having bulky phenoxathiin moiety
substituted at position-2 utilising carbon disulfide, amine and
phenoxathiinylchalcones as Michael acceptors in order to
enhance their biological and pharmacological activities.
Results and discussion
The starting chalcones, 3-phenyl/(4-chlorophenyl)-1-(phenox-
athiin-2-yl)propenones (1a,b) were prepared by the
SCSNH
O
O
CS2, THF
r.t., 2h
+
Ar
Ph
Ar
Ph
NH2
1a
2a
3a
S
Ar =
O
Scheme 1
O
R1 R2
O
SCSN
CS2, THF
r.t., 2h
+
R1 R2 NH
Ar
Ar
X
2
1a,b
3a-n
X
1a, X = H
1b, X = Cl
Scheme 2
* Correspondent. E-mail: mohamedbehalo@hotmail.com
PAPER: JC090719
JCR_12_2009 Book.indb 753
11/12/2009 15:36

754 JOURNAL OF CHEMICAL RESEARCH 2009
Conclusion
Experimental
All reactions were monitored by TLC using Merck Platen Kieselgel
60 F 25G. Chromatographic purification were performed on columns
packed with Merck silica gel 60, melting points are uncorrected.
IR spectra in KBr were recorded using a Perkin-Elmer 298
spectrophotometer. Mass spectra were obtained using a Shimadzu
GCMS-QP 1000 EX mass spectrometer. 1H and 13C NMR spectra
were obtained using 400 MHz and 100 MHz respectively in the
institute of organic chemistry, faculty of science and technology,
university of Urbino, Urbino. Italy. Microanalytical data was carried
out in the microanalytical centre, university of Cairo, Egypt.
The objectives of the present study were to synthesise and
investigate the biological activities of new phenoxathiin-
containing compounds. This aim has been verified by an
efficient three components synthesis of dithiocarbamate
derivatives 3a-n at room temperature from the reaction of
phenoxathiinylchalcones 1a,b, carbon disulfide and amines.
Biological activities
Some of the newly synthesised target compounds were evaluated
in vitro for their antibacterial activity against Bacillus subtilis,
Rhadococcus equii as Gram positive bacteria and Pseudomonas
aeruginosa and Escherichia coli as Gram negative bacteria.
They were also evaluated in vitro for their antifungal potential
against Candida albican and Fusarium solami. Agar diffusion
method was used for the determination of the preliminary
antibacterial and antifungal activity.24 Ampicillin trihydrate and
terbinafane were used as a reference drugs.
The results were recorded for each tested compound as the
average diameter of inhibition zones (r) of bacterial or fungal
growth around the disks in mm at 100 µg concentration using
dimethylsulfoxide (10 ml) as a solvent.
The results depicted in Table 2 revealed that most of the
tested compounds displayed variable inhibitory effect on the
growth of the tested organisms. Regarding the activity of the
dithiocarbamate series against both Gram positive and Gram
negative bacteria, the results showed that compounds 3c, 3f
and 3h have a significant antibacterial effect. Compounds 3c
and 3i showed the highest activity against Bacillus Subtilis
while 3a showed the lowest. On the other hand, the tested
compounds have no effect against Fusarium solami except
compounds 3c and 3j, they showed antifungal activity similar
to the reference drug Terbinafane.
General procedure for the synthesis of dithiocarbmates 3a–n
To stirred solution of amine 2 (1.5 mmole) in THF (20 mL), CS2
(3 mmole) was added. The chalcone 1 (1 mmole) was added and
the reaction mixture was stirred at room temperature for 2 h. Excess
carbon disulfide was removed and the crude product was purified by
column chromatography on silica gel and ethyl acetate/cyclohexane
as eluent.
3-Oxo-3-(phenoxathiin-2-yl)-1-phenylpropylpropyldithiocarba-
1
mate (3a): H NMR (DMSO-d6), d ppm = 1.07–1.11 (t, 3H, CH3),
1.95–2.11 (m, 2H, CH2), 3.32–3.37 (t, 2H, CH2N), 3.46–3.49 (d, 2H,
CH2CO), 4.85–4.93 (dd, 1H, CHS), 6.97–7.53 (m, 12H, ArH), 12.60
(s, 1H, NH, exchangeable); 13C NMR: 14.03(CH3), 22.17 (CH2),
39.92 (CHS), 47.56 (CH2CO), 52.41 (CH2N), 117.18, 117.42, 117.94,
124.89, 126.58, 126.65, 127.18, 128.22, 128.95, 130.13, 131.13,
135.17, 151.91, 156.87 (phenoxathiin and phenyl carbons), 191.10
(CO), 199.13 (CS); IR, 1680 (CO), 3187 (NH), 2923, 2854 (CH2),
1218 (CS) cm-1; MS: m/z: 465 (M+); Anal. Calcd for C25H23NO2S3
(465.65): C, 64.49; H, 4.98; N, 3.01. Found: C, 64.66; H, 5.12;
N, 3.21%.
3-Oxo-3-(phenoxathiin-2-yl)-1-phenylpropylcyclohexyldithiocarbamate
(3b): 1H NMR (DMSO-d6), d ppm = 1.39–1.67 (m, 6H, 3CH2),
1.98–2.29 (m, 4H, 2CH2), 3.79–3.84 (m, 1H, CHN), 4.19–4.28 (d,
2H, CH2CO), 5.06 (dd, 1H, CHS), 6.78–8.05 (m, 12H, ArH), 11.10
(s, 1H, NH, exchangeable); 13C NMR: 22.17, 28.86, 32.27 (5CH2),
39.78 (CHS), 42.72 (CH2CO), 52.28 (CHN), 117.60, 118.28, 125.15,
125.94, 126.35, 126.95, 127.63, 128.32, 129.25, 131.54, 133.52,
144.93, 150.98, 159.08 (phenoxathiin and phenyl carbons), 193.42
(CO), 196.22 (CS); IR, 1681 (CO), 3350 (NH), 2925, 2850 (CH2),
Table 1 Reaction of chalcones 1a,b with carbon disulfide and amines
Entry
Chalcone 1
Amine, R1R2NH 2
Product 3
M.p./°C
Yield/%
1
2
1a
Propylamine
Cyclohexylamine
Diethylamine
a
b
c
d
e
f
g
h
i
j
k
l
m
n
182 – 184
177 – 179
196 – 198
206 – 208
212 – 214
194 – 196
202 – 204
195 – 197
186 – 188
214 – 216
183 – 185
206 – 208
180 – 182
191 – 193
85
91
88
68
83
45
49
82
83
82
75
74
39
46
3
4
1-Amino-2-acetaldahyde diethylacetal
Benzylamine
5
6
Aniline
7
p-Tolidine
8
1b
Propylamine
9
Cyclohexylamine
Diethylamine
10
11
12
13
14
1-Amino-2-acetaldahyde diethylacetal
Benzylamine
Aniline
p-Tolidine
Table 2 Responses of various micro-organisms to some synthesised compounds
Compound
B. subtilis
R. equii
P. aeruginosa
E. Coli
C. albican
F. solami
3a
10
16
30
18
20
20
12
28
22
30
NT
16
18
28
0
16
20
18
0
0
15
20
0
0
15
18
0
14
12
14
0
0
0
3b
3c
8
3d
0
3e
0
0
8
0
3f
16
15
0
0
30
NT
28
26
18
0
30
NT
10
8
8
6
NT
11
0
3h
0
3i
0
3j
0
30
NT
12
NT
11
Ampicillin trihydrate
Terbinafane
Numbers in the table represent the inhibition zone diameter (r mm) of either fungal growth or bacterial cells for each compound;
r > 20 mm, high active; r > 12 mm, moderately active; r > 6 mm, slightly active; 0 no inhibition was observed; and NT means
not tested.
PAPER: JC090719
JCR_12_2009 Book.indb 754
11/12/2009 15:36

JOURNAL OF CHEMICAL RESEARCH 2009 755
1216 (CS) cm-1; MS: m/z: 505 (M+); Anal. Calcd for C28H27NO2S3
(505.71): C, 66.50; H, 5.38; N, 2.77. Found: C, 66.82; H, 5.47;
N, 2.68%.
4.12 (t, 1H, CHS), 4.14–4.27 (2q, 4H, 2CH2), 5.11–5.16 (m, 1H,
OCH), 6.92–8.06 (m, 11H, ArH), 9.84 (s, 1H, NH, exchangeable);
IR, 1692 (CO), 3270 (NH), 2936, 2845 (CH2), 1260 (CS) cm-1;
Anal. Calcd for C28H28ClNO4S3 (574.18): C, 58.57; H, 4.92; N, 2.44.
Found: C, 58.42; H, 4.80; N, 2.48%.
3-Oxo-3-(phenoxathiin-2-yl)-1-phenylpropyldiethyldithiocarbamate
(3c): 1H NMR (DMSO-d6), d ppm = 1.13–1.24 (2t, 6H, 2CH3), 3.66–
3.69 (d, 2H, CH2CO), 4.01–4.17 (2q, 4H, 2CH2), 5.82 (dd, 1H, CHS),
6.72–7.98 (m, 12H,ArH), 10.47 (s, 1H, NH, exchangeable); 13C NMR
11.25 (2CH3), 45.68 (CHS), 47.16 (2CH2), 47.93 (CH2CO), 117.94,
118.11, 118.80, 121.56, 122.37, 122.85, 125.13, 128.28, 128.49,
131.12, 134.22, 136.18, 154.76, 156.87 (phenoxathiin and phenyl
carbons), 191.22 (CO), 195.23 (CS); IR, 1704 (CO), 3378 (NH),
2980, 2844 (CH2), 1232 (CS) cm-1; MS: m/z: 479 (M+); Anal. Calcd
for C26H25NO2S3 (479.68): C, 65.10; H, 5.25; N, 2.92. Found: C,
65.27; H, 5.39; N, 2.88%.
1-(4-Chlorophenyl)-3-oxo-3-(phenoxathiin-2-yl)propylbenzyl-
dithiocarbamate (3l): 1H NMR (DMSO-d6), d ppm = 3.46 (s, 2H,
CH2), 3.85–3.89 (d, 2H, CH2CO), 5.30–5.35 (m, 1H, CH), 6.77–7.92
(m, 16H, ArH), 9.85 (s, 1H, NH, exchangeable); IR, 1700 (CO), 2938,
2840 (CH2), 1270 (CS) cm-1;Anal. Calcd for C29H22NO2S3Cl (548.14):
C, 63.55; H, 4.05; N, 2.56. Found: C, 63.72; H, 4.13; N, 2.63%.
1-(4-Chlorophenyl)-3-oxo-3-(phenoxathiin-2-yl)propylphenyl-
dithiocarbamate (3m): 1H NMR (DMSO-d6), d ppm = 3.23–
3.27 (d, 2H, CH2), 4.82–4.87 (m, 1H, CH), 6.97–8.01 (m, 16H,
ArH), 9.23 (s, 1H, NH, exchangeable); IR, 1680 (CO), 2945,
2825 (CH2), 1312 (CS); Anal. Calcd for C28H20NO2S3Cl (534.11):
C, 62.96; H, 3.77; N, 2.62. Found: C, 63.11; H, 3.85; N, 2.68%.
1-(4-chlorophenyl)-3-oxo-3-(phenoxathiin-2-yl)propyl-p-tolyldithio-
3-Oxo-3-(phenoxathiin-2-yl)-1-phenylpropyl(2,2-diethoxyethyl)
1
dithiocarbamate (3d): H NMR (DMSO-d6), d ppm = 1.24–135 (2t,
6H, 2CH3), 2.25–2.26 (d, 2H, CH2N), 4.05 (d, 2H, CH2CO), 4.07
(dd, 1H, CHS), 4.15–4.31 (2q, 4H, 2CH2), 5.06–5.10 (m, 1H, OCH),
7.20–7.95 (m, 12H, ArH), 8.75 (s, 1H, NH, exchangeable); IR, 1688
(CO), 3345 (NH), 2935, 2820 (CH2), 1315 (CS) cm-1; MS: m/z: 539
(M+); Anal. Calcd for C28H29NO4S3 (539.72): C, 62.31; H, 5.42; N,
2.60. Found: C, 62.45; H, 5.53; N, 2.49%.
1
carbamate (3n): H NMR (DMSO-d6), d ppm = 2.38 (s, 3H, CH3),
4.32–4.36 (d, 2H, CH2), 5.13–5.5.18 (m, 1H, CH), 6.79–7.95
(m, 15H, ArH), 9.87 (s, 1H, NH, exchangeable); IR, 1705 (CO),
3385 (NH), 2925, 2838 (CH2), 1310 (CS) cm-1; Anal. Calcd for
C29H22NO2S3Cl (548.14): C, 63.54; H, 4.05; N, 2.56. Found:
C, 63.68; H, 4.12; N, 2.62%.
3-Oxo-3-(phenoxathiin-2-yl)-1-phenylpropylbenzyldithiocarbamate
(3e): 1H NMR (DMSO-d6), d ppm = 3.72 (s, 2H, CH2), 3.78–3.82
(d, 2H, CH2CO), 4.67–4.71 (m, 1H, CH), 6.93–7.88 (m, 17H, ArH),
9.38 (s, 1H, NH, exchangeable); IR, 1685 (CO), 3335 (NH), 2945,
2830 (CH2), 1240 (CS) cm-1; MS: m/z: 513 (M+); Anal. Calcd for
C29H23NO2S3 (513.68): C, 67.81; H, 4.51; N, 2.73. Found: C, 68.11;
H, 4.72; N, 2.63%.
All strains were kindly supplied from Botany Department,
Faculty of Science, Benha University, Egypt.
3-Oxo-3-(phenoxathiin-2-yl)-1-phenylpropylphenyldithiocarba-
mate (3f): 1H NMR (CDCl3), d ppm = 3.35–3.38 (d, 2H, CH2),
4.65–4.69 (m, 1H, CH), 7.01–7.98 (m, 17H, ArH), 10.22 (s, 1H, NH,
exchangeable); IR, 1684 (CO), 2930, 2845 (CH2), 1252 (CS); Anal.
Calcd for C28H21NO2S3(499.67): C, 67.30; H, 4.24; N, 2.80. Found:
C, 67.13; H, 4.15; N, 2.72%.
Received 2 August 2009; accepted 24 November 2009
Paper 09/0719 doi: 10.3184/030823409X12594282884215
Published online: 8 December 2009
References
3-Oxo-3-(phenoxathiin-2-yl)-1-phenylpropylp-tolyldithiocarbamate
1
2
C.M. Buess, J. Am. Chem. Soc., 1955, 77, 6613.
R.N. Salvatore, S. Sahaba and K.W. Junga, Tetrahedron Lett.,2001,
42, 2055.
1
(3g): H NMR (DMSO-d6), d ppm = 2.25 (s, 3H, CH3), 4.12 (d, 2H,
CH2), 4.85–4.89 (m, 1H, CH), 6.92–7.50 (m, 16H, ArH), 10.98 (s, 1H,
NH, exchangeable); 13C NMR 23.24 (CH3), 48.31 (CHS), 51.23 (CH2-
C=O), 115.20, 118.24, 118.66, 120.12, 121.36, 121.42, 123.56, 125.68,
128.41, 128.54, 129.14, 131.26, 133.53, 133.76, 135.64, 144.58,
152.38, 154.82 (phenoxathiin and phenyl carbons), 192.46 (CO),
196.28 (CS); IR, 1690 (CO), 3364 (NH), 2930, 2825 (CH2), 1282 (CS)
cm-1; MS: m/z: 513 (M+); Anal. Calcd for C29H23NO2S3 (513.68): C,
67.81; H, 4.51; N, 2.73. Found: C, 68.05; H, 4.75; N, 2.67%.
3
4
A. Ziyaei-Halimjani and M.R. Saidi, J. Sulfur Chem., 2005, 26, 149.
F. Busque, P.D. March, M. Fegueredo, J. Font and L. Gonzales, Eur. J.
Org. Chem., 2004, 1492.
5
6
7
8
9
N. Azizi, F. Aryanasab, L. Torkiyan, A. Ziyaei and M.R. Saidi, J. Org.
Chem., 2006, 71, 3634.
N. Azizi, B. Pourhasan, F. Aryanasab and M.R. Saidi, Synlett, 2007,
1239..
C. Rafin, E. Veignie, M. Sancholle, D. Postal, C. Len, P. Villa and
G. Ronco, J. Agric. Food Chem., 2001, 48, 5283.
P.J. Nieuwenhizen, A.W. Ehlers, J.G. Haasnoot, S.R. Janse, J. Reedijk and
E.J. Baerends, J. Am. Chem. Soc., 1999, 121, 163.
L. Ronconi, C. Marzano, P. Zanello, M. Corsini, G. Miolo, C. Macca,
A. Trevisan and D. Fregona, J. Med. Chem., 2006, 49, 1648.
1-(4-Chlorophenyl)-3-oxo-3-(phenoxathiin-2-yl)propyl propyldithio-
1
carbamate (3h): H NMR (DMSO-d6), d ppm = 1.12–1.15 (t, 3H,
CH3), 2.02–2.10 (m, 2H, CH2), 3.25–3.28 (t, 2H, CH2N), 3.41–3.45
(d, 2H, CH2CO), 5.12–5.18 (dd, 1H, CH), 7.07–7.98 (m, 11H,
ArH), 11.35 (s, 1H, NH, exchangeable); IR, 1695 (CO), 3325 (NH),
2933, 2840 (CH2), 1310 (CS) cm-1; Anal. Calcd for C25H22NO2S3Cl
(500.10): C, 60.04; H, 4.43; N, 2.80. Found: C, 59.82; H, 4.30;
N, 2.86%.
10 M.R. Wood, D.J. Duncalf, S.P. Rannard and S. Perrier, Org. Lett., 2006,
8, 553.
11 J.J. Tegeler, H.H. Ong and J.A. Profitt, J. Heterocyclic Chem., 1983,
20, 867.
12 Y.M. Al-Hiari and B.A. Sweileh, Asian J. Chem.,2006, 18, 2285.
13 O. Maior, D. Gavriliu and S. Stoia, South. Braz. J. Chem., 1995, 3, 79.
14 G.W. Rewcastle, G.J. Atwell, B.D. Palmer, P.D. Boyd, B.C. Baguley and
W.A. Denny, J. Med. Chem.,1991, 34, 491.
15 Y. Girard, P. Hamel and D. Delorme, US Pat. 1990, 5036067; Chem.
Abstr., 1991, 115, 232258.
16 S. Ionescua, D. Gavriliu, O. Maior and M. Hillebrand, J. Photochem.
Photobiol., 1999, 124, 67.
17 T. Constantinescu, A. Mischie, O. Maior, F. Badea, M. Vasilescu,
M.T. Caproiu, R. Socoteanu and D. Nourescu, Rev. Roum. Chim., 2000,
45, 1009.
18 C.T. Supuran, A. Scozzafava, F. Briganti, G. Loloiu and O. Maior
J. Enzyme Inhib., 1998, 31, 291; C.A., 1999, 130, 49076.
19 O.A. Attanasi, L.D. Crescentini, G. Favi, P. Filippone, G. Giorgi,
F. Mantellini, G. Moscatelli and M.S. Behalo, Org. Lett., 2009, 11, 2265.
20 Y.A. Issac, I.G. El-Karim, S.G. Donia and M.S. Behalo, Sulf. Lett., 2002,
25, 183.
1-(4-Chlorophenyl)-3-oxo-3-(phenoxathiin-2-yl)propyl cyclohexyl-
dithiocarbamate (3i): 1H NMR (DMSO-d6), d ppm = 1.65–1.95
(m, 6H, 3CH2), 2.40–2.48 (m, 4H, 2CH2), 3.07–3.09 (d, 2H, CH2CO),
3.76–3.79 (m, 1H, CHN),, 5.38–5.48 (dd, 1H, CHS), 7.08–8.01
(m, 11H, ArH), 11.55 (s, 1H, NH, exchangeable); 13C NMR 21.95,
29.24, 31.78 (5CH2), 39.92 (CH-S), 44.16 (CH2-C=O), 50.17 (CHN),
118.21, 118.54, 123.76, 125.62, 126.57, 127.16, 127.65, 128.77,
130.48, 131.63, 132.76, 142.83, 152.15, 157.94 (phenoxathiin
and phenyl carbons), 188.67, (CO), 193.84 (CS); IR, 1680 (CO),
3400 (NH), 2920, 2850 (CH2), 1250(CS) cm-1; Anal. Calcd for
C28H26NO2S3Cl (540.16): C, 62.26; H, 4.85; N, 2.59. Found: C,
62.45; H, 4.97; N, 2.66%.
1-(4-Chlorophenyl)-3-oxo-3-(phenoxathiin-2-yl)propyldiethyldithio-
1
carbamate (3j): H NMR (DMSO-d6), d ppm = 1.09–1.14 (2t, 6H,
2CH3), 3.45–3.49 (d, 2H, CH2–C=O), 4.22–4.29 (2q, 4H, 2CH2),
4.91 (m, 1H, CHS), 6.94–8.01 (m, 11H, ArH), 9.58 (s, 1H, NH,
exchangeable); IR, 1687 (CO), 2930, 2835 (CH2), 1245 (CS) cm-1;
Anal. Calcd for C26H24NO2S3Cl (514.12): C, 60.74; H, 4.71; N, 2.72.
Found: C, 60.94; H, 4.88; N, 2.78%.
21 Y.A. Issac, I.G. El-Karim, M.S. Behalo, A.A. Aly and S.G. Donia, Olaj,
Szappan, Kozmetika, 2008, 57, 128.
22 M.S. Behalo, Phosphorus, Sulfur Silicon Relat. Elem, 2009, 184, 206.
23 E. Lescot, N.P. Buu-Hoi and N.D. Xuong, J. Chem. Soc., 1956, 2408.
24 C. Leifert, S. Chidbouree, S. Hampson, S. Workman, D. Sigee,
H.A.S. Epton and A. Harbour, J Appl. Bact., 1995, 78, 97.
1-(4-Chlorophenyl)- 3-oxo-3-(phenoxathiin-2-yl)propyl (2,2-diethoxy-
ethyl)dithiocarbamate (3k): 1H NMR (CDCl3), d ppm = 1.15–128 (2t,
6H, 2CH3), 2.18–2.22 (d, 2H, CH2N), 3.84 – 3.88 (d, 2H, CH2CO),
PAPER: JC090719
JCR_12_2009 Book.indb 755
11/12/2009 15:36

Copyright of Journal of Chemical Research is the property of Science Reviews 2000 Ltd. and its content may
not be copied or emailed to multiple sites or posted to a listserv without the copyright holder's express written
permission. However, users may print, download, or email articles for individual use.