Investigation of cationic surfactants and sulfonamides and their nanoparticles as biocides against sulfur reducing bacteria in the petroleum industry

Article abstract of DOI:10.1080/15533174.2013.778877

A series of cationic ammonium surfactants (1-3) and sulfonamides (4-5) were synthesized and characterized using elemental analysis and FT-IR spectroscopy. The nanostructures of the synthesized surfactants and sulfonamides as silver and zinc nanoparticles

Full text of DOI:10.1080/15533174.2013.778877

This article was downloaded by: [University of York]
On: 08 October 2014, At: 06:56
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
Synthesis and Reactivity in Inorganic, Metal-Organic,
and Nano-Metal Chemistry
Publication details, including instructions for authors and subscription information:
http://www.tandfonline.com/loi/lsrt20
Investigation of Cationic Surfactants and Sulfonamides
and Their Nanoparticles as Biocides Against Sulfur
Reducing Bacteria in the Petroleum Industry
Salwa M. I. Morsy a b & Mohamed M. Ibrahim a c
a Department of Chemistry, Faculty of Science , Taif University , Kingdom of Saudi Arabia
b Applied Surfactant Laboratory, Egyptian Petroleum Research Institute , Nasr City , Cairo ,
Egypt
c Chemistry Department, Faculty of Science , Kafr El-Sheikh University , Kafr El-Sheikh ,
Egypt
Accepted author version posted online: 30 Oct 2013.Published online: 21 Nov 2013.
To cite this article: Salwa M. I. Morsy & Mohamed M. Ibrahim (2014) Investigation of Cationic Surfactants and Sulfonamides
and Their Nanoparticles as Biocides Against Sulfur Reducing Bacteria in the Petroleum Industry, Synthesis and Reactivity in
Inorganic, Metal-Organic, and Nano-Metal Chemistry, 44:4, 530-536, DOI: 10.1080/15533174.2013.778877
To link to this article: http://dx.doi.org/10.1080/15533174.2013.778877
PLEASE SCROLL DOWN FOR ARTICLE
Taylor & Francis makes every effort to ensure the accuracy of all the information (the “Content”) contained
in the publications on our platform. However, Taylor & Francis, our agents, and our licensors make no
representations or warranties whatsoever as to the accuracy, completeness, or suitability for any purpose of the
Content. Any opinions and views expressed in this publication are the opinions and views of the authors, and
are not the views of or endorsed by Taylor & Francis. The accuracy of the Content should not be relied upon and
should be independently verified with primary sources of information. Taylor and Francis shall not be liable for
any losses, actions, claims, proceedings, demands, costs, expenses, damages, and other liabilities whatsoever
or howsoever caused arising directly or indirectly in connection with, in relation to or arising out of the use of
the Content.
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. Terms & Conditions of access and use can be found at http://
www.tandfonline.com/page/terms-and-conditions

Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 44:530–536, 2014
Copyright ꢀ Taylor & Francis Group, LLC
C
ISSN: 1553-3174 print / 1553-3182 online
DOI: 10.1080/15533174.2013.778877
Investigation of Cationic Surfactants and Sulfonamides
and Their Nanoparticles as Biocides Against Sulfur Reducing
Bacteria in the Petroleum Industry
Salwa M. I. Morsy1,2 and Mohamed M. Ibrahim1,3
1Department of Chemistry, Faculty of Science, Taif University, Kingdom of Saudi Arabia
2Applied Surfactant Laboratory, Egyptian Petroleum Research Institute, Nasr City, Cairo, Egypt
3Chemistry Department, Faculty of Science, Kafr El-Sheikh University, Kafr El-Sheikh, Egypt
by consumption of cathodically formed hydrogen.[1] Control of
A series of cationic ammonium surfactants (1–3) and sulfon-
amides (4–5) were synthesized and characterized using elemental
analysis and FT-IR spectroscopy. The nanostructures of the syn-
thesized surfactants and sulfonamides as silver and zinc nanopar-
ticles (Ag/ZnNPs) were prepared and characterized using trans-
mission electron microscope. The TEM image of AgN-1–3 is a
spherical shape with narrow diameter, whereas ZnN-4–6 compos-
ites are roughly spherical. The size analysis demonstrated the av-
erage diameter of 50–55 nm for the composite. The antimicrobial
activity of the synthesized surfactants and sulfonamides as well as
their nanostructures were investigated as potential biocides against
sulfur reducing bacteria. The values of the inhibition zone diam-
eters are gradually increased by increasing the concentration of
the tested biocides and the maximum inhibition diameters for all
biocides are obtained at 5 mg/mL. The results also showed that the
sulfonamides and their nanocomposites have higher biocidal activ-
ities than those of the cationic ammonium surfactants biocides and
their nanoparticles.
biogenic sulfide production decreases operating costs and can be
achieved through the application of biocides.[4] Environmental
regulations and development of oil reservoirs in environmentally
sensitive areas have spurred the development of easily degrad-
able “green” biocides that are less toxic to higher, no target
organisms, such as fish.[5]
Quaternary ammonium salts and their nanoparticles consid-
ered efficient inhibitor of SRB[6,7] are also relatively nontoxic
and inexpensive and has been successfully used to inhibit sulfide
production in oil field settings.[8,9] The efficiency of cationic sur-
factants is based on their ability to disturb the integral bacterial
membrane by a combined hydrophobic and electrostatic ad-
sorption phenomenon at the membrane water interface making
disorganization.[10] The cell membrane is predominantly neg-
atively charged as compared with eukaryotic cells.[11]. Hence,
the positive charge of the cationic amphiphile facilitates their
interaction with the bacterial membrane.
Sulfonamides were the first effective chemotherapeutic
agents employed systematically for the prevention and cure
of bacterial infections in humans.[12,13] Sulfonamides represent
an important class of medicinally important compounds which
are extensively used as antibacterial agent. It interferes with p-
aminobenzoic acid in the biosynthesis of tetrahydrofolic acid,
which is a basic growth factor essential for the metabolic process
of bacteria.
The objective of this article is to present novel synthe-
ses and characteristics of cationic ammonium surfactants and
sulfonamides and their loaded silver and zinc nanoparticle
(Ag/ZnNPs), respectively, were revealed and investigated as
potential biocides against SRB.
Keywords biocides, cationic surfactants, petroleum industry, silver
and zinc nanoparticles, sulfonamides
INTRODUCTION
Sulfate-reducing bacteria (SRB) in oil environments was
rapidly recognized as responsible for the production of H2S.
The formed H2S is the principal agent in the disastrous effects
caused by SRB.[1] It contaminates gas and stored oil, precipitates
ferrous sulfide that plugs injection wells, and promotes precip-
itates ferrous sulfide that plugs injection wells, and promotes
corrosion of iron and steel in the absence of oxygen (anaerobic
corrosion).[2,3] Another principal mechanism by which SRB are
involved in corrosion is their ability to depolarize iron surfaces
EXPERIMENTAL
Received 4 January 2013; accepted 19 February 2013.
This work was financially supported by Taif University, Saudi Ara-
bia, Project No.: 1-433-1819.
Material and Methods
The chemical structures of the synthesized cationic surfac-
tants (1–3) and sulfonamides (4–6) were performed using (Vario
Elementar Analyzer). The IR spectroscopy was also used to
Address correspondence to Mohamed M. Ibrahim, Chemistry De-
partment, Faculty of Science, Taif University, Kingdom of Saudi Ara-
bia. E-mail: ibrahim652001@yahoo.com
530

INVESTIGATION OF CATIONIC SURFACTANTS
531
determine the chemical structures of these compounds using
Genesis Fourier transformer FT-IR. The size and morphology
of silver nanoparticles and the nanostructure of the synthesized
quaternary ammonium and sulfonamide biocides with silver and
zinc nanostructures were investigated by transmission electron
microscope (TEM) using JEM-(Jeol)-2010.
Synthesis
Synthesis of the quaternary biocides (1–3)
0.1 mol of triethyl amine was refluxed by 0.1 mol of alkyl
bromides namely: octyl bromide, decyl bromide, and dodecyl
bromide in presence of 100 mL acetone as a solvent for 6 hr.[14]
The reaction product (designated as 1–3) was filtered off and
recrystallized twice from acetone, Scheme 1.
SCH. 2. Chemical structures of the synthesized sulfonamide biocides.
Preparation of the silver nanoparticles
The silver nanoparticles colloidal solution was prepared us-
ing the chemical reduction method, which involves reduction
of silver nitrate (AgNO3) in distilled water using efficient re-
ducing.[17] In typical experiment, 50 mL of (1 mmol/L) solution
of AgNO3 was added to 5 mL of 1% trisodium citrate drop
wise under heating and stirring conditions. The reaction was
preceded until the color is turned to pale yellow as an evident
for the formation of silver nanoparticles.[18]
Preparation and stabilization of silver nanoparticle by (1–3)
The prepared silver nanoparticles solution (20 mL) was
mixed with 5 mL saturated solution of the synthesized qua-
ternary compounds (1–3) in deionized water and stirred con-
tinuously for 24 h till the yellow color becomes paler. Then
the solution was centrifuged at 12000 rpm to obtain the pre-
cipitate of quaternary-silver nanoparticles. The precipitate was
washed with cold water to remove the unreacted materials. The
quaternary-silver nanoparticles solution was used for ultraviolet
measurements and TEM image, while the precipitate was used
for infrared analysis.[19]
SCH. 1. Chemical structures of the synthesized quaternary biocides.
Synthesis of the sulfonamides (4–6)
A mixture of 0.1 mol of 4,4/-biphenyl-disulfonyl chlo-
ride 0.2 mol of 4-aminobenzenesulfonamide, 6-chloro-4-amino
benzene-1,3-disulfonamide or 5-amino-1,3,4-thiadiazole-2-
sulfonamide, and 0.2 mol of pyridine were refluxed in dry
ether (250 mL) for 4 h.[15,16] In case of synthesis of 5-
amino-1,3,4-thiadiazole-2-sulfonamide derivative, the Scotten-
Baumann conditions were used, and the corresponding amine
was dissolved in 15 mL solution 2.5 M NaOH and cooled to
–20◦C in a salt-ice bath. After the reactions were completed,
the solvent was evaporated in vacuum, adjusted to pH 2 with
5 N HCl, and the precipitated bis-sulfonamides were filtered
and recrystallized from aqueous ethanol to give biphenyl 1,4-
disulfonamide biocides (Scheme 2).
Synthesis of sulfonamide-Zn-nanocomposite
50 mL solution of the different sulfonamides in dimethyl
formamide was added to 50 mL suspension of Zn-nanoparticles
prepared from the milling of elemental Zn. The concentration of
the metal to sulfonamides was 1:3 by weight.[20] The solutions
were mixed together and allowed to stir for 24 h at 25◦C.
Antimicrobial Studies
The synthesized quaternary ammonium compounds and the
sulfonamides and their nanoparticles and nanocomposites were
screened for their antimicrobial activity against sulfur reducing
bacteria using agar well diffusion method.[21,22]

532
S. M. I. MORSY AND M. M. IBRAHIM
TABLE 1
The elemental analysis of the synthesized compounds
Calcd. (Found)
Compound
M. wt.
C%
H%
N%
Br%
Cl%
S%
1
2
3
4
5
6
294.31
322.37
350.42
622.70
847.72
638.73
57.13 (56.56)
59.61 (59.01)
61.70 (61.08)
46.30 (46.27)
34.00 (33.77)
30.09 (29.88)
10.96 (10.85)
11.26 (11.15)
11.51 (11.39)
3.53 (3.50)
23.80 (23.60)
22.10 (21.90)
4.76 (4.71)
4.34 (4.30)
4.00 (3.96)
9.00 (8.96)
9.91 (9.84)
17.54 (17.42)
27.15 (26.88)
24.79 (24.54)
22.80 (22.57)
—
—
—
—
—
—
—
—
—
—
20.57 (20.52)
22.70 (22.54)
30.12 (29.91)
8.36 (8.30)
—
Growing of microorganisms
The bacterial strains were cultured on nutrient medium, while
Minimum inhibitory concentration
The antimicrobial activity of the tested biocides against the
the fungi strains were cultured on malt medium. For bacteria, SRB bacteria was expressed as the minimum inhibitory con-
the broth media were incubated for 24 h. As for fungus, the broth centration (MIC) values, defined as the lowest concentration of
media were incubated for approximately 48 h, with subsequent compounds inhibiting the development of visible growth after
filtering of the culture through a thin layer of sterile Sintered 24 h of incubation. The MIC values were determined by dilution
Glass G2 to remove mycelia fragments before the solution con- method.[22] The compounds tested were dissolved in a mixture
taining the spores was used for inoculation.
of distilled water/alcohol (3/1; v/v) at various concentrations
and the 1 mL aliquot of the biocides solutions was added to
the 14 mL agar media. The final concentrations of the tested
biocides in the medium were 300, 200, 100, 40, 20, 10, and
4 mg/mL.
Measurements of resistance and susceptibility
For preparation of discs and inoculation, 1 mL of inocula
were added to 50 mL of agar media (40◦C) and mixed. The
agar was poured into 120 mm Petri dishes and allowed to cool
at room temperature. Wells (6 mm in diameter) were cut in the
agar plates using proper sterile tubes. Then, holes filled up to the
surface of agar with 0.1 mL of the tested biocides dissolved in
DMF (1 mg/mL DMF). The plates were left on a leveled surface,
incubated for 24 h at 37◦C and then the diameter of the inhi-
bition zones were measured.[23] The inhibition zone formed by
these compounds against the particular test bacterial strain deter-
mined the antibacterial activities of the synthetic compounds.
The mean value obtained for three individual replicates was
used to calculate the zone of growth inhibition of each sam-
ple. Microorganisms The biocidal activity of the synthesized
compounds and their nanostructures were tested against Desul-
fomonas pigra ATCC 29098.
RESULTS AND DISCUSSION
Structure Confirmation
The microelemental analysis showed that the calculated and
the found ratios of the different elements in the compounds
are near to each other by the ratio of 99% (see Table 1). That
showed the purity of the prepared compounds. Their IR spectral
bands (Table 2) showed the presence of the absorption bands
at 2950, 2790, and 3040 cm−1, which confirmed the presence
of the methyl (CH3), methylene (CH2), and positively charged
nitrogen groups (N+). The obtained data showed that the syn-
thesized compounds have identical structures as represented in
Schemes 1 and 2.
TABLE 2
FTIR spectral bonds of the synthesized compounds
Compound
CH3
CH2
R4N+
Aromatic (CH)
SO2
NH
NH2
1
2
3
4
5
6
2950
2940
2954
—
—
—
2790
2810
2800
—
—
—
3040
3040
3040
—
—
—
—
—
—
3075
3082
3058
—
—
—
—
—
—
3260
3248
3255
—
—
—
1162, 1332
1142, 1315
1187, 1342
3279, 3380
3277, 3385
3270, 3394

INVESTIGATION OF CATIONIC SURFACTANTS
533
FIG. 2. TEM of the reduced silver nanoparticles.
the surfactant molecules on the silver nanoparticles. The TEM
images further revealed the stabilization of silver nanoparticles
due to interaction with the quaternary biocide molecules. Fig-
ures 5–7 show the TEM micrograph of the Zn-nanoparticle com-
posite, showing that the particles were roughly spherical. The
size analysis demonstrated the average diameter of 50–55 nm
for the composite.
FIG. 1. (a) UV spectra of the silver nanoparticles; (b) UV spectra of silver
nanoparticles loaded with the quaternary ammonium biocides.
Antimicrobial Activities
The biocidal activities of the synthesized quaternary am-
monium biocides and their silver loaded nanoparticles and the
sulfonamides and their zinc nanocomposites in terms of the
inhibition zone diameter (in mm) and MIC were determined
and the results were listed in Table 3 and 4, respectively.
It is clear that the values of the inhibition zone diameters are
gradually increased by increasing the concentration of the tested
Ultraviolet Spectroscopy (UV)
It is observed from Figure 1 the presence of a strong absorp-
tion peak at approximately wavelength 430 nm and intensity of
0.49 absorbance intensity from the surface Plasmon resonance
of nanosized silver particles.[24,25] The good symmetric absorp-
tion peak implies that the size distribution of the nanoparticles
is narrow.[26] The loading of the quaternary ammonium biocides
on the silver nanoparticles solution disappear the peak at 430 nm
as shown in Figure 1. That is due to the reduction of the negative
charge on the colloidal particles. Metal particles in their aqueous
colloidal dispersions are usually acquiring negative charges due
to the adsorbed anions around the particles.
Transmission Electron Microscope (TEM)
The size and morphology of silver nanoparticles and the
nanostructure of the synthesized quaternary ammonium and
sulfonamide biocides with silver and zinc nanostructures were
investigated by TEM. The TEM image reduced of the silver
nanoparticles (Figure 2) indicates that these silver particles are
spherical shape with narrow diameter.[27] The particles size
distribution of the quaternary biocides 1 and 2 capped silver
nanoparticles (Figures 3 and 4) indicate that the size distri-
bution of silver nanoparticles is narrow sphere. These figures
showed the spherical silver nanoparticles with a corona of the
FIG. 3. TEM of the decyl triethyl ammonium bromide capped silver nanopar-
quaternary surfactants, which related to the self-assembling of ticles.

534
S. M. I. MORSY AND M. M. IBRAHIM
FIG. 4. TEM of the dodecyl triethyl ammonium bromide capped silver
nanoparticles.
FIG. 6. TEM of biphenyl 1,4-disulfonamide biocides 5.
biocides and the maximum inhibition diameters for all biocides
are obtained at 5 mg/mL. It is also clear that the antimicrobial
activities are gradually increased by increasing the alkyl chain
length. The dodecyl derivative.[3] showed the maximum antimi-
crobial activity against the tested bacterial strain (Desulfomonas
pigra ATCC 29098). The shorter alkyl chain length deriva-
tives[1–3] showed lower biocidal activity in terms of inhibition
zone diameter.[28–31] The biocidal tests were done in dimethyl
formamide as a solvent. The DMF has no effect on the growth
of the tested bacterial strains as described in recent works. The
inhibition zone diameter tests were done for the silver nanopar-
ticles loaded quaternary biocides (AgN-1–3) against the SRB
bacteria (Desulfomonas pigra ATCC 29098). The obtained re-
sults showed the high potency of the nanoparticle-quaternary
biocides compared to their quaternary biocides in the molec-
ular from. The inhibition zone diameters were nearly double,
which indicates the increasing efficiency of the nanoforms of
the biocides in overcoming the fatal effect of the SRB bacteria
in the infected area especially in the oilfields. The values of the
inhibition zone diameter of the sulfonamides[4–6] were listed in
Table 3. It is clear that the inhibition zone diameters range be-
tween 14–17 mm at 1 mg/mL and 17–21 mm at 5 mg/mL. that
is considerably large values compared to the quaternary ammo-
nium biocides. That showed the high inhibiting effect of the sul-
fonamide biocides, which can be attributed to the presence of the
sulfur atoms in the chemical structures of these biocides[32,33]
FIG. 5. TEM of biphenyl 1,4-disulfonamide biocides 4.
FIG. 7. TEM of biphenyl 1,4-disulfonamide biocides 6.

INVESTIGATION OF CATIONIC SURFACTANTS
535
TABLE 3
in some fields is limited due to the developed microbial resis-
tance against QAS after longer periods of applications, their
high acute toxicity and low biodegradability.[30]
Antimicrobial activities (a,b) in terms of inhibition zone
diameter (mm) at different doses (1, 2, 5 mg/mL) of the
synthesized quaternary and sulfonamide biocides and their
nanostructures against sulfur reducing bacteria (Desulfomonas
pigra ATCC 29098)
The mode of action of the quaternary ammonium biocides
in the biocidal action is generally accepted that the cationic
biocides can adsorb onto negatively charged cell membranes,
which will then lead to decrease in the osmotic stability of the
cell and leakage of intracellular constituents.[31–33] However, the
exact mechanism of the antimicrobial action is still unknown and
several other mechanisms that may contribute to the antimicro-
bial action have also been suggested, such as the formation of
an impermeable coat on the bacterial surface,[32] uptake of low
molecular weight biocides that will interact with electronega-
tive substances in the cell and inhibition of bacterial growth
through chelation of trace metals.[32] The mechanism for the in-
teraction may be different for gram-positive and gram-negative
bacteria.
AgN-1–3 biocides have high potency against the SRB bacte-
ria (Desulfomonas pigra ATCC 29098). That can be attributed to
the presence of the alky chains that increase the surface activity
of these compounds. This can be explained by the different cell
membrane structure of the two bacterial types.[30] The external
layer of the outer membrane of the SRB bacteria is almost en-
tirely composed of lipopolysaccharides and proteins that restrict
the entrance of biocides and amphiphilic compounds.[30,34] The
perturbation of this outer membrane requires a fine tuning of the
hydrophobic-hydrophilic balance (HLB).
Inhibition zone diameter in (mm) at
different dose (mg/mL)
Compound
1 mg/mL
2 mg/mL
5 mg/mL
1
2
3
12.3
13.5
14.2
22
24
25
14
16
17
25
14
15
16.3
25
26
29
15.5
17
18.5
28
31
34
15
17
18
27
30
32
17
19
21
31
35
39
AgN-1
AgN-2
AgN-3
4
5
6
4-nanocomposite
5-nanocomposite
6-nanocomposite
29
31
aThe data is a mean of five replicates with relative error ∼7%.
bThe antimicrobial activity expressed as the diameter of the inhibi-
tion zone formed in presence of the tested compounds.
It is clear that the values of the inhibition zone diameters are
gradually increased by increasing the concentration of the tested
biocides and the maximum inhibition diameters for all biocides
are obtained at 5 mg/mL. It is also clear that the antimicrobial
activities are the maximum antimicrobial activity against the
tested bacterial strain (Desulfomonas pigra ATCC 29098). The
shorter alkyl chain length derivative[1] showed lower biocidal
activity in terms of inhibition zone diameter.[35–37] The biocidal
tests were done in dimethyl formamide as a solvent. The DMF
has no effect on the growth of the tested bacterial strains as
described in recent works.[38]
MIC values for the synthesized quaternary biocides 1–3 are
summarized in Table 4. The tested biocides show high activity
level against SRB bacteria (Desulfomonas pigra ATCC 29098)
with MIC values >600 mg/mL (Table 4). The MIC values for
the synthesized quaternary ammonium biocides in the form of
the nanoparticles (AgN-1–3) are summarized in Table 4. While,
in case of the sulfonamides, the MIC values range between 300
and 150 mM. The MIC values of the zinc nanocomposite loaded
of the sulfonamides were decreased considerably to reach to
100–25 mM (Table 4).
ion zone diameter are describing the general behavior of the
tested biocides against the different bacterial genera. The bio-
cidal activity of the quaternary ammonium compounds (QAS)
TABLE 4
Minimum inhibitory concentration values (μM) of the
synthesized quaternary and sulfonamide biocides and their
nanostructures against sulfur-reducing bacteria (Desulfomonas
pigra ATCC 29098)
Minimum inhibitory
Dose, mg/mL
concentration (μM)
1
2
3
>600
>600
>600
200
100
50
AgN-1
AgN-2
AgN-3
4
5
6
300
300
150
100
50
Comparing the antibacterial activities of the silver and zinc
nanostructures showed that the zinc nanocomposites have higher
efficiency as biocide against SRB. That can be attributed to the
influence of zinc nanostructures. It was reported that the zinc
and zinc oxide nanoparticles and also zinc nanocomposites have
high toxicity for the different types of bacteria. Here, the results
4-nanocomposite
5-nanocomposite
6-nanocomposite
25
aThe data is a mean of five replicates with relative error ∼7%.

536
S. M. I. MORSY AND M. M. IBRAHIM
¨
showed identical trend in the activity increasing against SRB 13. Genc¸, Y.; Ozkanca, R.; Bekdemir, Y. Ann. Clin. Microbiol. Antimicrob.
bacteria.
The results of the biocidal activities of the two types of the
synthesized biocides showed their high efficiency as biocides in
defeating the growth of the sulfur reducing bacteria in oilfields
applications.
2008, 7, 17–20.
14. Morsy, S. M.; Ghazy, E. A.; Badawi, A. M. Egypt. j. Microbiol. 2004, 39,
29–40.
15. Badawi, A.; El-Maghraby, A.; Haroun, B.; Soliman, H. Pharmazie 1980,
35, 748–753.
16. Supuran, C. T.; Ilies, M. A.; Scozzafava, A. Eur. J. Med. Chem. 1998, 33,
739–752.
17. Fang, J.; Zhong, C.; Mu, R. Chem. Phys. Lett. 2005, 401, 271–275.
18. Sileikaite, A.; Prosycevas, I.; Puiso, J.; Juraitis, A.; Guobiene, E. J. Mater.
Sci. 2006, 12, 287–291.
CONCLUSION
In this study, we have synthesized two types of the biocides
that were quaternary ammonium bromide and sulfonamides in
their molecular and nanoparticle forms. The molecular forms
of the different biocides showed good biocidal activity against
19. Tamulevicius, S.; Prosycevas, I.; Guobiene, A.; Puiso, J. Solid State Phe-
nom. 2004, 99, 175–180.
20. Huang, J.; Liu, C.; Xiao, H.; Wang, J.; Jiang, D.; Erdan, G. U. Int. J.
Nanomed. 2007, 2, 775–784
SRB bacteria at 2 and 5 mg/mL. The nanoparticles forms of the 21. Cooper, R. E. Analytical Microbiology, Academic Press, New York and
London, 1972.
different biocides were highly potent against the SRB bacteria
than their corresponding molecular form.
22. Hubert, S. K.; Nguyen, P. D.; Walker, R. D. J. Vet. Diagn. Invest. 1998, 10,
164–168.
23. Shah, S. S.; Khan, M. S.; Ullah, H.; Awan, M. A. J. Colloid Interface Sci.
1997, 186, 382–368.
24. Asiri, M.; Badahadah, O. K. Molecules 2007, 12, 1796–1804.
REFERENCES
1. Cord-Ruwisch, R.; Kleinitz, W.; Widdel, F. J. Pet. Technol. 1987, 39,
97–106.
25. Biyala, M. K.; Sharma, K.; Swami, M.; Fahmi, N.; Singh, R. V. Transition
Met. Chem. 2008, 33, 377–381.
2. Hongfang, L.; Liming, X.; Jiashen, Z.; Jing, L. Mater. Perform. 2000, 39,
52–55.
3. Maillard, U. Y. J. Appl. Microbiol. Symp. Suppl. 2002, 92, 165–169.
4. Nemati, M.; Jenneman, G. E.; Voordouw, G. Biotechnol. Bioeng. 2001, 74,
424–434.
5. Frey, R. Today’s Chem. Work 1998, 7, 34.
6. Greene, E. A.; Hubert, C.; Nemati, M.; Jenneman, G. E.; Voordouw, G.
Environ. Microbiol. 2003, 5, 607–617.
7. Haveman, S. A.; Greene, E. A.; Stilwell, C. P.; Voordouw, J. K.; Voordouw,
G. J. Bacteriol. 2004, 186, 7944–7950.
8. Ciaraldi, S. W.; Ghazal, H. H.; Abou Shadey, T. H.; El-Leil, H. A.; El-
Raghy, S. M. Progress in combating microbiologically induced corrosion in
oil production, paper no. 181. Corrosion/99. NACE International, Houston,
TX, 1999.
9. Telang, A. J.; Ebert, S.; Foght, J. M.; Westlake, D. W. S.; Jenneman, G. E.;
Gevertz, D.; Voordouw, G. Appl. Environ. Microbiol. 1997, 63, 1785–1793.
10. Castillo Expo´sito, J. A. Studies on antimicrobial activity of arginine-based
surfactants and chemoenzymatic synthesis of novel amphiphiles based on
L-arginine D-fogamine; Thesis, Universitat Autonoma de Barcelona, Spain,
2006.
26. Hutchison, J. E. Am. Chem. Soc. Nanochem. 2008, 2, 395–402.
27. Ibrahim, M. N.; Sharif, S. E. A. Electron. J. Chem. 2007, 4, 531–535
28. Pernak, J.; Mirska, I.; Kmiecik, R. Eur. J. Med. Chem. 1999, 34, 765–
771.
29. Skrzypczak, A.; Brycki, B.; Mirska, I.; Pernak, J. Eur. J. Med. Chem. 1997,
32, 661–668.
30. Garcıa, M. T.; Ribosa, I.; Guindulain, T.; Sanchez Leal, J.; Vives-Rego, J.
Environ. Pollut. 2001, 111, 169–175.
31. Pe´rez, L.; Pinazo, A.; Garc´ıa, M. T.; Lozano, M.; Manresa, A.; Angelet,
M.; Vinardell, M. P.; Mitjans, M.; Pons, R. M. R. Infante 2009, 44, 1884–
1892.
32. Rabea, E. I.; Badawy, M. E. T.; Stevens, C. V.; Smagghe, G.; Steurbaut, W.
Biomacromolecules 2003, 4, 1457–1465.
33. Devlieghere, F.; Vermeulen, A.; Debevere, J. Food Microbiol. 2004, 21,
703–714.
34. Oros, G.; Cserhati, T.; Forgacs, E. Chemosphere 2003, 52, 185–193.
35. Negm, N. A.; Aiad, I. A.; Tawfik, S. M. J. Surf. Deterg. 2010, 13, 503–
511.
36. Negm, N. A.; Zaki, M. F.; Salem, M. A. I. J. Disp. Sci. Technol. 2010, 31,
1390–1395.
11. Oren, Z.; Hong, J.; Shai, Y. J. Biol Chem. 1997, 272, 14643–14649.
12. Mengelers, M. J.; Hougee, P. E.; Jansson, L. H.; Van Miert, A. S. J. Vet.
Pharmacol. Therap. 1997, 20, 276–28.
37. Negm, N. A.; Elkholy, Y. M.; Ghuiba, F. M.; Zahran, M. K.; Mahmoud, S.
A.; Tawfik, S. M. J. Disp. Sci Technol. 2011, 32, 512.
38. Negm, N. A. Egypt. J. Chem. 2002, 45, 483–499.