Advances in Biological Chemistry, 2011, 1, 122-127
doi:10.4236/abc.2011.13015 Published Online November 2011 (http://www.SciRP.org/journal/abc/ ABC ).
Published Online November 2011 in SciR es. http://www.scirp.org/journal/ABC
Synthesis and fungicidal activity of some sulphide derivatives
of O-phenyl-N-substituted phenylcarbamates
F. E. Adelowo1*, I. A. O. Ojo2, O. S. Amuda1
1Department of Pure and Applied Chemistry, Ladoke Akintola University of Technology, Ogbomoso, Nigeria;
2Department of Chemistry, Obafemi Awolowo University, Ile-Ife, Nigeria.
Received 5 August 2011; revised 13 September 2011; accepted 24 September 2011.
ABSTRACT
Monosulphides of O-phenyl-N-substituted phenylcar-
bamates were prepared by the reaction between O-
phenyl-N-substituted phenylcarbamates and sulph-
ur dichloride while the corresponding disulphides
were prepared by the reaction between O-phenyl-N-
substituted phenylcarbamates and sulphur monoch-
loride. The synthesized compounds were character-
ized by elemental analysis, thin layer chromatogra-
phy (TLC), Fourier-transform infrared, 1H and 13C
nuclear magnetic resonance spectroscopic techniques.
In vitro fungicidal assay of these sulphides against
Fusarium oxysporum, Aspergillus niger, Aspergillus
flavus and Rhizopus stolonifer showed that they were
more fungicidal than their parent carbamates. The
synthesized sulphides were more active towards As-
pergillus niger and Aspergillus flavus. There was lit-
tle or no variations in the fungicidal activities of the
synthesized monosulphides and disulphides of O-phen-
yl-N-substituted phenyl carbamates.
Keywords: Fungicidal Activity; Sulphide Derivatives;
Synthesis
1. INTRODUCTION
Variations in the structure of sulphur-containing com-
pounds have led to increased fungicidal activity [1,2].
Fungicides are chemicals that combat the attack of vari-
ous fungi species. Organosulphur compounds are eco-
nomically important fungicides that play a significant
role in the production of agricultural crops and in the
preservation of in dustrial products [3].
Dithiocarbamates and their derivatives were one of
the early groups of organic sulphur fungicides. They
were discovered by Tisdale and Williams in 1934 [4].
The properties of the dithiocarbamates could be changed
by replacement of the sulphur hydrogen with metals or
other substituents [5] Extending the alkyl chain could
lead to loss of activity while optimum activity could be
achieved with two methyl groups on the nitrogen of the
dithiocarbamates [2].
Sulphur derivatives of carbonates were among the re-
cently introduced fungicides. They were prepared from
the reaction between carbon disulphide, sulphur and
caustic soda [6]. Tetrathiocarbonate and thiozolidine-
dione gave a broad spectrum control of nematodes, nu-
trifying bacteria and a wide range of soil fungi [7,8].
The stability of the metal-chelate [9] formed between
the heavy metals present in fungi cells and the fungicide
sulphur determines the fungicidal activity of these or-
ganosulphur compounds. Formation of such metal-che-
lates would increase the hydrophobic property of metal
ions and this would enable them to pass through lipoid
layers of cellular membranes to the fungus cells, thereby
leading to their poisoning [10,11].
A wide variety of functional groups have been intro-
duced into the structure of carbamates. These include
sulfenyl, thiono, thiocarbonyl, acyl, sulfinyl, sulfonyl
phosphinothioyl and diatazole groups [12-18]. The most
widely used functional group for the derivatization of
carbamates is the sulfenyl group [15,16,19-22]. Several
types of N-sulfenylated carbamates have shown higher
fungicidal activity than their corresponding parent com-
pounds [1].
This report is concerned with the sulfenylation of
some O-phenyl-N-substituted phenylcarbamates and the
potential use of the derivatized products as fungicides.
This is in line with our research efforts on the synthesis,
structure-activity relationships of organosulphur com-
pounds.
2. MATERIALS AND METHODS
2.1. Reagents and Solvents
Solid reagents were re-crystallized while solvents were
re-distilled. Toluene and di-ethyl ether were dried over
sodium wire. Sulphur monochloride was re-distilled over
sulphur and collected at 138˚C - 139˚C. Similarly sul-

F. E. Adelowo et al. / Advances in Biological Chemistry 1 (2011) 122-127 123
phur dichloride was purified by distillation and the frac-
tion collected at 58˚C - 59˚C.
2.2. Synthesis of Parent Compounds
O-phenyl-N-substituted phenylcarbamates were pre-
pared by the reaction between phenyl chloroformate and
substituted aniline in the presence of pyridine which was
used for trapping the generated HCl. The general proce-
dure for the synthesis of O-phenyl-N-sub stituted phenyl-
carbamates was as reported previously [23].
2.2.1. O-Phen yl - N- (3 -ni trop henyl) carbamate
Phenyl chloroformate (7.8 g, 6.3 cm3, 0.05 mol) and
3-nitroaniline (6.9 g, 0.05 mol) gave O-phenyl-N-(3-
nitrophenyl) carbamate (9.0 g, 70%) as a bright yellow
crystalline solid on re-crystallization from methanol;
(Found: C, 61.10; N, 10.95. Calc. for C13H10N2O4: C,
60.46; N, 10.85%); m.p. 110˚C - 112˚C. The TLC (etha-
nol/DMSO, 3:1) gave a single spot, Rf = 0.82; 1H
(C3D6O): 7. 2 - 8 .8 (Ar-H, m, 9H), 9.8(N-H, b.s., 1H).
2.2.2. O-Phen yl - N- (4 -ni trop henyl) Carbamate
Phenyl chloroformate (7.8 g, 6.3 cm3, 0.05 mol) and
4-nitroanaline (6.9 g, 0.05 mol) gave O-phenyl-N-(4-ni-
trophenyl) carbamate (10.6 g, 82%) as a yellow crystal-
line solid on re-crystallization fro m methanol; (Found : C,
60.59; N, 9.98. Calc. for C13H10N2O4: C, 60.46; N,
10.85%); m.p. 118˚C - 119˚C. The TLC (ethanol/DMSO,
3 : 1) gave a single spot, Rf = 0.84; 1H (C3D6O): 7.1 - 8.9
(Ar-H, m, 9H), 9.8(N-H, b.s., 1H)
2.2.3. O-Phen yl - N- (4 -chloro phen yl ) Carbamate
Phenyl chloroformate (7.8 g, 6.3 cm3, 0.05 mol) and
4-chloroaniline (6.4 g, 0.05 mol) gave O-phenyl-N(4-
chlorophenyl) carbamate (9.7 g, 78%) as a dark brown
crystalline solid on re-crystallization from methanol;
(Found: C, 63.10; N, 5.78. Calc. for C13H10ClNO2: C,
63.03; N, 5.66%); m.p. 126 ˚C - 127˚C. The TLC (etha-
nol/DMSO, 3:1) gave a single spot, Rf = 0.76; 1H
(C3D6O): 7.1 - 8.1 (Ar-H, m, 9H), 9.4 (N-H, b.s., 1H).
The infrared spectra of the synthesized carbamates
showed strong carbonyl stretching bands between 1700
cm–1 and 1705 cm–1 while the secondary amide bands
appeared between 3300 cm–1 and 3350 cm–1 for N-H
stretching.
2.3. Synthesis of Symmetrical
Bis-[N-phenoxycarbonyl-N-(3-nitrophenyl)]
Monosulphide
O-phenyl-N-(3-nitrophenyl) carbamate (1.29 g, 0.005
mol) was dissolved in carbon tetrachloride (20 cm3). To
the brown solution was added excess pyridine (10cm3).
Chilled sulphur dichloride, SCl2 (0.52 g, 0.4 cm3, 0.005
mol) dissolved in carbon tetrachloride (10 cm3) was
added dropwisely from a dropping funnel. The whole
reaction mixture was set up in a 250 cm3 three-necked
reaction flask fitted with a reflux condenser, a dropping
funnel and a magnetic stirrer. The reaction mixture was
stirred for 1 hour at 20˚C in a fume cupboard. White
fumes of hydrogen chloride, which disappeared with
time was produced (Figure 1). An equimolar quantity of
O-phenyl-N-(3-nitrophenyl) carbamate (1.29 g, 0.005
mol) dissolved in carbon tetrachloride (20 cm3) was
added to the reaction mixture through the dropping fun-
nel. Further evolution of white fumes was observed. The
reaction mixture was stirred for another 1 hour and fi-
nally left to stir overnight at room temperature The reac-
tion mixture was washed with 10% hydrochloric acid
(100 cm3) solution in a separatory funnel. The organic
layer was separated and washed with distilled water
CHO
65
CNH
O
NO
2
+Cl-S-Cl CCl
4
Pyridine
CHO
65
CNSCl
O
NO
2
+PyHCl
Pyridine
CCl
4
CHO
65
CNH
O
NO
2
CHO
65
C N
O
NO
2
N COCH
65
O
NO
2
+
S
PyHCl
Figure 1. Synthesis of bis-[N-phenoxycarbonyl-N-(3-nitrophenyl)] monosulphide.
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F. E. Adelowo et al. / Advances in Biological Chemistry 1 (2011) 122-127 124
(3 × 100 cm3). The brown organic layer was separated
from the aqueous layer, dried with anhydrous sodium
sulphate and filtered under suction. Volatile solvents
were removed by means of a rotary evaporator to leave
an oily residue which was solidified on cooling. The
crude product was re-crystallized from methanol to give
the desired product, bis-[N-phenoxycarbonyl-N-(3-nitro-
phenyl)] monosulphide, (I) (2.16 g, 79%) as brown crys-
tals of m.p. 134˚C - 135˚C; (Found: C, 56.09; N, 10.35;
S, 6.68. Calc. for C26H18N4O8S: C, 57.13; N, 10.25; S,
5.87%); TLC (ethanol/DMSO, 3:1) gave a single spot
with Rf = 0.65; 1H (DMSO): 7.8 - 8.5 (Ar-H, m, 18H).
The infrared spectrum of the synthesized compound
showed a strong carbonyl absorption at 1720 cm–1 and
absence of amide band of N-H stretching.
The above procedure was used for the synthesis of
other symmetrical monosulphides.
2.3.1. Bis-[N-phenoxycarbonyl-N-(4-nitrophenyl]
Monosulphide
O-phenyl-N-(4-nitrophenyl) carbamate [2 × (1.30 g,
0.005 mol)] and sulphur dichloride (0.52 g, 0.4 cm3,
0.005 mol) gave the product bis-[N-phenoxycarbonyl-N-
(4-nitrophenyl)] monosulphide (1.78 g, 65%), as brown
crystals of m.p. 140˚C - 141˚C; (Found: C, 57.10; N,
10.02; S, 6.01. Calc. for C26H18N4O8S: C, 57.13; N,
10.25; S, 5.87%). TLC (ethanol/DMSO, 3:1) gave a sin-
gle spot with Rf = 0.64; 1H (DMSO): 7.5 - 8.2 (Ar-H, m,
18H).
2.3.2. Bis-[-N-phenoxycarbonyl-N-(4-chlorophenyl)]
Monosulphide
O-phenyl-N-(4-chlorophenyl) carbamate [2 × (1.24 g,
0.005 mol)] and sulphur dichloride (0.52 g, 0.4 cm3,
0.005 mol) gave the product, bis-[N-phenoxycarbonyl-
N-(4-chlorophenyl)] monosulphide (1.84 g, 70%) as a
brown crystalline solid on re-crystallization from me-
thanol; (Found: C, 59.29; N, 5.51; S, 6.71. Calc. for
C26H18Cl2N2S: C, 59.43; N, 5.33; S, 6.10%); m.p. 78˚C -
79˚C. TLC (ethanol/DMSO, 3:1) gave a single spot with
Rf = 0.65; 1H (DMSO): 7.4 - 8.9 (Ar-H, m, 18H).
2.4. A General Procedure for the Synthesis of
Symmetrical Disulphides
2.4.1. Synthesis of Bis-[N-phenoxycarbonyl-
N-(3-nitr ophe nyl)] Disulphide
To a solution of O-phenyl-N-(3-nitrophenyl) carbamate
(1.29 g, 0.005 mol) dissolved in carbon tetrachloride (20
cm3), was added excess triethylamine, Et3N (10 cm3).
Chilled sulphur monochloride, S2Cl2 (0.68 g, 0.4 cm3, 5
mmol), dissolved in carbon tetrachloride (10 cm3) was
added dropwisely from a dropping funnel, whilst the
reaction mixture was maintained below 10˚C by the ad-
dition of ice to the water bath in wh ich the reaction ves-
sel stood. White fumes which disappeared with time
were produced. The reaction mixture was kept stirring
for another 30 minutes after the addition of sulphur mo-
nochloride was completed. An equimolar quantity of
O-phenyl-N-(3-nitrophenyl) carbamate (1.29 g, 0.005
mol), dissolved in carbon tetrachloride (20 cm3) was
added dropwisely to the reaction mixture. Further evolu-
tion of white fumes as observed. The reaction mixture
was allowed to stir at a temperature below 10˚C for an
additional 30 minutes and finally left to stir overnight at
room temperature (Figure 2). The solid, triethylamine
CHO
65
CNH
O
NO
2
+Cl-S-S-Cl EtN
3
CC l
4
CHO
65
CNSSCl + EtN HCl
3
O
NO
2
+PyHCl
CCl
4
CHO
65
CNH
O
NO
2
CHO
65
C N
O
NO
2
NCOC H
65
O
NO
2
+
S
Et N
3
S
EtN HCl
3
Figure 2. Synthesis of bis-[N-phenoxycarbonyl-N-(3-nitrophenyl)] disulphide.
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F. E. Adelowo et al. / Advances in Biological Chemistry 1 (2011) 122-127 125
hydrochloride was removed by filtration. The filtrate
was washed with 10% hydrochloric acid (100 cm3) solu-
tion in a separatory funnel. The organic layer was
washed with distilled water (3 × 102 cm3), dried with
anhydrous sodium sulphate and filtered. Volatile solvents
were removed from the filtrate by means of a rotary
evaporator to leave an oil, which was so lidified on stand-
ing. The crude product was re-crystallized from metha-
nol to give the desired product, bis-[N-phenoxycar-
bonyl-N-(3-nitrophenyl)] disulphide (II) (1.9 g, 65%), as
a brown crystalline solid, m.p. 108˚C - 1 09˚C; (Found : C,
54.01; N, 9.57; S, 10.30. Calc. for C26H18N4O8S2: C,
53.97; N, 9.68; S, 11.08%). TLC (ethanol/DMSO 3:1)
gave a single spot, Rf = 0.51; 1H (DMSO): 7.2 - 7.8
(Ar-H, m, 18H). The infrared spectrum of the synthe-
sized compound showed a strong carbonyl absorption at
1725 cm–1 and absence of amide band of N-H stretching.
The above procedure was used for the synthesis of other
symmetrical disulphides.
2.4.2. Bis-[N-phenoxycarbonyl-N-(4-nitrophenyl)]
Disulphide
O-phenyl-N(4-nitrophenyl) carbamate [2 × (1.30 g, 0.005
mol)] and sulphur monochloride (0.68 g, 0.4 cm3, 0.005
mol.) gave the product, bis-[N-phenoxycarbonyl-N-(4-
nitrophenyl)] disulphide (2.26 g, 78%) as a brown crystal-
line solid, m.p. 150˚C - 151˚C; (Found: C, 53.88; N, 9.59;
S, 10.54. Calc. for C26H18N4O8S2: C, 53.97; N, 9.68; S,
11.08%). TLC (ethanol/DMSO 3:1) gave a single spot, Rf
= 0.50. 1H (DMSO): 7.5 - 7.9 (Ar-H, m, 18H).
2.4.3. Bis-[N-phenoxycarbonyl-N-(4-chlorophenyl)]
Disulphide
O-phenyl-N-(4-chlorophenyl carbamate [2 × (1.24 g , 0.005
mol)] and sulphur monochloride (0.68 g, 0.4 cm3, 0.005
mol.) gave the product, bis-[N-phenoxycarbonyl-N-(4-
chlorophenyl)] disulphide as a brown crystalline solid
(2.26 g, 81%), m.p. 118˚C - 119˚C; (Found: C, 56.33; N,
5.14; S, 12.97. Calc. for C26H18Cl2N2O4S2: C, 56.01; N,
5.03; S, 11.49%). TLC (ethanol/DMSO 3:1) gave a single
spot, Rf = 0.53. 1H (DMSO): 7.8 - 8.4 (Ar-H, m, 18H).
2.5. Biological Screening
Potato Dextrose Agar (PDA) plates were flooded with
spore suspension of each fungus. About 6mm diameter
filter paper discs were sterilized in petri dishes at 160˚C
for 2 hours. With the aid of sterilized pair of forceps,
filter paper discs that have been soaked in solutions of
various concentrations of each synthesized compound
were put on the surface of inoculated PDA plates. Filter
paper discs were also soaked in the standard and the
control and then placed on the surface of inoculated
PDA plates. All the PDA plates were put in an incubator
at room temperature. The growth diameter of the fungal
spore was measured at every 24 hours until when there
was a complete growth of fungus on the control plate.
The minimum concentration of each synthesized com-
pound that gave 100% inhibition of fungus growth was
taken as the ‘Minimal Inhibitory Concentration’ (MIC)
of the compound [2]. The IC50 (Inhibitory concentration
of the synthesized compound at 50% inhibition of the
fungus population) was extrapolated from the graph of
percentage inhibition (%I) of fungus against concentra-
tion of the synthesized compound [2,24].
3. RESULTS AND DISCUSSION
The values of the minimal inhibitory concentration (MIC)
and the 50% inhibitory concentration (IC50) of the syn-
thesized compounds are presented in Table 1.
The data obtained clearly showed that the sulphide
derivatives retained the fungicidal activity exhibited by
the corresponding phenyl carbamates. Not only sulphide
derivatives retained the fungicidal activity of their parent
carbamates, they were found to be significantly more
fungicidal to all the fungi species. The inhibitory effect
of O-phenyl carbamates on the fungi species has been
probably enhanced by the presence of sulphur. Organic
sulphur compounds could migrate into the fungus cells
and take part in chemical reactions that could lead to
increase in activity [5].
Sulphur derivatives of O-phenyl-N-phenyl carbamate
showed greater activity towards Aspergillus species.
From the results obtained in Table 1, the activity of the
synthesized monosulphides and disulphides (in terms of
MIC) towards Aspergillus species doubled that of other
fungi species. This is an indication that Aspergillus spe-
cies were more susceptible to sulphur derivatives of O-
phenyl-N-phenyl carbamate than Fusarium oxysporum
and Rhizopus stolonifer.
Generally, compounds with substituents at the meta
position of the benzen e ring sh owed greater activity than
those with substituents at the para position. In all the
synthesized compounds, activity decreased with de-
crease in concentration. This is in agreement with our
earlier findings [2]. Increase the number of sulphur at-
oms did not contribute significantly to the fungicidal
activity of the synthesized compounds. The monosul-
phides were even more active than most of their corre-
sponding disulphides as indicated by their IC50 results
(Table 1)
When compared with the results obtained in the pre-
vious paper, the sulphide derivatives of O-phenyl-N-
phenyl carbamate showed greater activity than the sul-
phide derivatives of O-ethyl-N-phenyl carbamate [23].
The delocalization of electrons that takes place in the
phenoxy groups of sulphide derivatives of O-phenyl-N-
phenyl carbamate would increase the nucleophlic prop-
erty of these compounds and this could lead to increase
in activity [2].
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Table 1. Inhibitory effect of the synthesized compounds on the fungi species through MIC and IC50 in ppm.
Aspergillus
niger Aspergillus flavus Rhizopus stolonifer Fusarium oxysporum
S/N Synthesized compounds MIC IC50 MIC IC50 MIC IC50 MIC IC50
1 O-phenyl-N-(3-nitrophenyl) carbamate 50 25 50 24 50 27 50 26
2 O-phenyl-N-(4-nitrophenyl) carbamate 100 45 100 48 100 55 100 52
3 O-phenyl-N-(4-chlorophenyl) carbamate 100 49 100 47 100 60 100 58
4 Bis-[N-phenoxycarbonyl-N-(3-nitrophenyl)]
monosulphide 10 5 10 4 20 13 20 15
5 Bis-[N-phenoxycarbonyl-N-(4-nitrophenyl)]
monosulphide 25 13 25 15 50 26 50 26
6 Bis-[N-phenoxycarbonyl-N-(4-chlorophenyl)]
monosulphide 25 11 25 12 50 20 50 23
7 Bis-[N-phenoxycarbonyl-N-(3-nitrophenyl)]
disulphide 10 07 10 6 20 15 20 14
8 Bis-[N-phenoxycarbonyl-N-(4-nitrophenyl)]
disulphide 25 17 25 15 50 28 50 27
9 Bis-[N-phenoxycarbonyl-N(4-chlorophenyl)]
disulphide 25 12 25 12 50 23 50 24
10 Phenylmercury acetate (standard) 5 1 5 1 5 2 5 2
11 DMSO/H2O (8:2) (Control) 0 0 0 0 0 0 0 0
4. CONCLUSIONS
In the continuation of our research efforts on the synthe-
ses and structural activity of organic sulphur compounds
as potential fungicides, we have studied the fungicidal
activity of sulphur derivatives of O-phenyl-N-phenyl car-
bamates and the results obtained showed that there was
an improvement in the fungicidal activity when com-
pared with their parent compounds and the earlier pre-
pared sulphur derivatives of O-ethyl-N-phenyl carbamate.
REFERENCES
[1] Lamberth, C. (2004) Sulfur chemistry in crop protection.
Journal of Sulfur Chemistry, 25, 39-62.
doi:10.1080/17415990310001612290
[2] Adelowo-Imeokparia, F., Faboya, O.O.P. and Ojo, I.A.O.,
(2005) Synthesis and fungicidalactivity of some phenyl
carbamates. International Journal of Chemistry, 15, 101-
111.
[3] Lukens, R.J. (1971) Chemistry of fungicidal action. Cha p-
man and Hall Ltd., London, 1-138.
[4] Metcalf, R.L. (1971) Chemistry and biology of pesticides.
In: White-Stevens, R., Ed., Pesticides in The Environ-
ment, R. Dekker, New York, 1.
[5] Cremlyn, R. (1979) Pesticides: Preparation and mode of
action. John Wiley and Sons, Ltd., Hoboken, 114-115.
[6] Young, D.E. (1988) U.S. Patent No. 726144.
[7] Ayodele, E.T. (1994) Studies in the synthesis and fungi-
cidal activity of some substituted benzyl-2-hydroxyethyl
oligosulphide and related compounds. Ph.D thesis, Uni-
versity of North London, London.
[8] Sonawane L.V. and Bari, S.B. (2011) Synthesis and spec-
tral characterization of some novel n-substituted 2,4-Thi-
a-zolidinedione. International Journal of Biological Che-
mistry, 5, 68-74.doi:10.3923/ijbc.2011.68.74
[9] Rich, S. (1960) Fungicidal chemistry in plant pathology.
Academy Press Ltd., New York, 588.
[10] Eyring, H., (1966) Untangling biological reactions. Sci-
ence, 154, 1609- 1613.
[11] Pattan, S.R., Suresh, C., Pujari, V.D., Reddy, V.V.K., Rasal
V.P. and Koti, B.C. (2005) Synthesis and antidiabetic ac-
tivity of 2-amino5’(4-sulphonylbenzylidine)-2,4-thiazoli-
dinedione]-7-chloro-6-fluoro-benzothiazole. Indian Journal
of Chemistry, 44, 2404-2408.
[12] Grogan, C.H.; Rice, L.M. and Reid, E.E. (1955) Dithiols
and derivatives. Journal of Organic Chemistry, 20, 50-
58. doi:10.1021/jo01119a009
[13] Field, L., Owen, T.C., Crenshaw, R.R. and Bryan, A.W.
(1961) Organic disulfides and rela ted sub stance s. IV. Thiol-
sulfonates and disulfides containing 2-aminoethyl moie-
ties. Journal of the American Chemical Society, 83, 4414-
4417. doi:10.1021/ja01482a027
[14] Szczepanski, C.V., Heindl, J.; Hoyer, G.A. and Schroder,
E. (1977) Biologically active substances in plants. II:
Synthesis and antimicrobial activity of some unsymmet-
rical oligosulphides. European Journal of Medicinal
Chemistry: Chimica TherapeuticaI, 12, 279-284.
[15] Fahmy, M.A.H. and Fukuto, T.R. (1981) N-sulfinylated
de- rivatives of methylcarbamate esters. Journal of Agri-
cultural and Food Chemistry, 29, 567-572.
doi:10.1021/jf00105a034
[16] Ayodele, E.T.; Hudson, H.R., Ojo, I. A.O. and Pianka, M.
(2000) Organosulfur compounds aspotential fungicides:
C
opyright © 2011 SciRes. ABC

F. E. Adelowo et al. / Advances in Biological Chemistry 1 (2011) 122-127 127
The preparation and properties of some substituted ben-
zyl 2-hydroxylethyl oligosulfides. Journal of Phosphorus,
Sulfur and Silicon, 159, 123-142.
doi:10.1080/10426500008043656
[17] Mori, M., Takagi, M., Noritake, C. and Kagabu, S. (2008)
2, 4-Dioxo-1,3-thiazolidine derivatives as a lead for new
fungicide. Journal of Pesticide Science, 33, 357-363.
doi:10.1584/jpestics.G08-15
[18] Vedavathi, M., Somashekar, B, Sreenivasa, G.M. and
Jayachandran, E. (2010) Synthesis, characterization and
anti-microbial activity of fluoro benzothiazole incorpo-
rated with 1,3,4-Thiadiazole. Journal of Pharmaceutical
Sciences and Research, 2, 53-63.
[19] Reid, E.E. (1960) Organic chemistry of bivalent sulphur.
Chemical Publishing Co. Inc., New York, III, 363-367.
[20] Kharasch, N. (1961) Organic sulphur compounds. Per-
gamon Press, Oxford, 30-51.
[21] Kuhle, E. (1970) One hundred years of sulfenic acid
chemistry, sulfenyl halide synthesis. Synthesis, 11, 560-
580.
[22] Ayodele, E.T. (2005) Preparation and glass house screen-
ing of some substituted benzyl-2-hydroxylethyl oligosul-
fides. Science Focus, 10, 56-62.
[23] Adelowo-Imeokparia, F. and Ojo, I.A.O. (2006) Synthe-
sis and fungicidal activity of some sulphide derivatives of
O-ethyl-N-substituted phenylcarbamates. Pakistan Jour-
nal of Scientific and Industrial R esearch, 49, 324-329.
[24] Tabakova, S. and Dodoff, N. (1995) Effect of platinum
(II) complexes of benzoic and 3-methoxybenzoic acid
hydrazides on Saccharomyces serevisiae. Zeitschrift für
Naturforschung, 50c, 732-743.
C
opyright © 2011 SciRes. ABC