Open Journal of Synthesis Theory and Applications, 2012, 1, 23-30
http://dx.doi.org/10.4236/ojsta.2012.13005 Published Online October 2012 (http://www.SciRP.org/journal/ojsta)
Antifunga l Pot en tia l of Transition Me tal
Hexacyanoferrates against Fungal Diseases of Mushroom
Charu Arora Chugh, Dipti Bharti
Department of Chemistry, Lovely Professional University, Jalandhar, India
Received July 9, 2012; revised August 12, 2012; accepted September 5, 2012
ABSTRACT
Ferrocyanides of Co(II), Ni(II), Cu(II), Zn(II) and Cd(II) were synthesized and characterized by IR spectra, magnetic
susceptibility, thermal gravimetric analysis, elemental analysis and X ray diffraction studies. Antimicrobial potential of
these complexes have been evaluated. Antifungal screening of these complexes has been carried out against Mycogone
perniciosa and Verticillium fungicola causing wet and dry bubble diseases of button mushroom respectively. Nickel
ferrocyanide has been found to be most effective against Mycogone perniciosa with 60% inhibitory effect while cad-
mium ferrocyanide has exhibited significant potential of 85% against Verticillium fungicola.
Keywords: Verticilium Fungicola; Mycogone Perniciosa; Biocidal Potential; Transition Metal Hexacyanoferrates
1. Introduction
Many of the transition metal ions in the living systems
work as enzymes or carriers in macrocyclic ligand field
environment. Therefore meaningful research in this di-
rection might generate simple models for biologically
occurring metallo enzymes and thus will help in devel-
oping our understanding of biological systems. These
ligands are also of theoretical interest as they are capable
of furnishing an environment of controlled geometry and
ligand field strength [1-5]. Synthesis of a number of poly-
dentatemacrocyclic ligands and their metal complexes
has been reported in literature [6].Transition metals have
an important place within medicinal biochemistry. Re-
view of literature has revealed significant progress in
utilization of transition metal complexes as drugs to treat
several human diseases like carcinomas, lymphomas, in-
fection control etc. These complexes act as therapeutic
and antimicrobial agents [7-13]. Transition metals exhibit
different oxidation states and can interact with a number
of negatively charged molecules. This activity of transi-
tion metals has started the development of metal based
drugs with promising pharmacological application and
may offer unique therapeutic opportunities. To provide
an update on recent advances in the medicinal use of
transition metals, a Medline search has been carried out
to identify the recent relevant literature [14,15].
These complexes may possess antimicrobial activity
against pathogenic fungi being used as a test organism in
the present study. It is well established that metal ferro-
cyanides acts as adsorbent[16,17], ion-exchangers [18, 19]
and photosensitizers [20].Transition metals such as zinc,
copper, cobalt, manganese, iron have been reported to be
essential for crops. They remain in soil in small quantity
and known as micronutrient. If the deficiency of these
elements is detected in soil these are recommended to be
added to soil with fertilizer or in form of top dressing.
Thus these metals act as micronutrient in trace quantity
and hence application of metal complexes in combination
with other ecofriendly chemicals/botanicals may be evalu-
ated for antimicrobial potential.
Mushrooms can provide more than just taste and tex-
ture for our meals-they actually have a surprisingly high
nutritional value also. White button mushrooms have a
surprising amount of nutrients including niacin, ribofla-
vin, folate, phosphorus, iron, panthothenic acid, zinc, po-
tassium, copper, magnesium, vitamin B6, selenium and
thiamin. In addition, white button mushroom extract has
been found to reduce the size of some cancer tumors and
slow down the production of some cancer cells. It is most
prominently linked to reducing the risk of breast and
prostate cancer. The yield of the crop is severely affected
by fungal pathogens Mycogone perniciosa and Verticil-
lium fungicola causing wet and dry bubble diseases of
button mushroom respectively. During the last decade V.
fungicola has become less sensitive to the only approved
chemical (prochloraz) that is still effective to treat infec-
tion. Moreover, it is expected that prochloraz will be
banned from commercial mushroom growing. Therefore,
alternative strategies to control the disease are urgently
needed. Wet bubble caused by M. perniciosa is a disease
that often occurs on mushroom farms. It can be of very
C
opyright © 2012 SciRes. OJSTA

C. A. CHUGH ET AL.
24
severe (when there are practically no healthy mushrooms
left on the beds), and not that much (unitary diseased
mushrooms) depending on the time when the infection
occurred; and the degree of infection.
Keeping in view the above facts present study has been
undertaken to synthesize, characterize and evaluate anti-
fungal activity of complexes of Mn(II), Co(II), Ni(II),
Cu(II), Zn(II) and Cd (II) against Mycogone perniciosa
and Verticillium fungicola causing wet and dry bubble
diseases of mushroom respectively.
2. Materials and Methods
2.1. Synthesis of Metal Ferrocyanides
Six transition metal ferrocyanides namely manganese fer-
rocyanide, cobalt ferrocyanide, nickel ferrocyanide, cop-
per ferrocyanide, zinc ferrocyanide and cadmium ferro-
cyanide were synthesized following Kourim’s method
[21]. A solution of potassium ferrocyanide (167 ml, 0.1
M) was added to solution of desired metal salt (500 ml,
0.1 M) with constant stirring at room temperature. A
slight excess of metal salt solution markedly improves
the coagulation of the precipitate. The reaction mixture
was heated on a water bath at 80˚C for 3 - 4 hrs, and al-
lowed to stand at ambient temperature for 24 hrs. The
precipitate was filtered under vacuum and washed thor-
oughly with double distilled water. It was dried in an
oven at 60˚C. The dried product was ground and sieved
to 100 mesh size. Coloured powders thus obtained were
stable on exposure of air and moisture. All the synthe-
sized complexes were found to be insoluble in water.
These were characterized on the basis of elemental analy-
sis, carried out on Carlo Erba 1108 CHN analyzer and
Atomic Absorption Spectrophotometer (Perkin Elmer
3100), IR spectra (recorded on Bio-Rad FTIR spectro-
photometer), magnetic susceptibility measurement (re-
corded on VSM-155), molar conductivity measurement
and X ray diffraction studies. The data has been reported
in Tables 1-9.
2.2. Collection of Fungal Cultures
Two fungal pathogens namely Mycogone perniciosa and
Verticillium fungicola causing wet and dry bubble dis-
eases of button mushroom respectively, have been col-
lected from Department of Plant Pathology, College of
Agriculture, G.B. Pant University of Agriculture and Tech-
nology, Pantnagar. Both these fungal pathogens were
grown on potato dextrose agar (PDA) medium and incu-
bated at 20˚C and 28˚C respectively.
2.3. Screening of Metal Complexes for
Fungicidal Activity
Paper disc method, based on diffusion capacity of test che-
mical(s) through agar medium has been used for pre-
liminary screening of antifungal activity of metal com-
plexes [22]. Fungal plug were placed at the center of as-
say plate containing sterilized PDA and allowed to grow.
After circular growth of about 2 - 3 cm diameter four
sterilized paper disc (two loaded with 20 l aqueous sus-
Table 1. Elemental analysis data of metal ferrocyanides.
% found (calculated)
Metal
Com-
plexes Metal Fe N C H
MnFC 28.56
(29.23)
14.66
(14.86)
22.59
(22.36)
20.67
(19.17)
1.69
(1.61)
CoFC 32.12
(32.22)
15.30
(15.27)
21.16
(22.97)
19.65
(19.70)
1.11
(1.10)
NiFC 27.85
(27.93)
13.00
(13.28)
18.79
(19.19)
16.51
(17.14)
2.22
(2.30)
CuFC 27.10
(27.32)
12.10
(12.01)
18.12
(18.07)
14.75
(15.49)
3.13
(3.03)
ZnFC 32.84
(32.95)
14.10
(14.08)
20.40
(21.18)
17.74
(18.16)
1.51
(1.45)
CdFC 50.12
(51.47)
12.58
(12.79)
20.38
(19.24)
17.71
(16.50)
0.26
(0.00)
Table 2. Infrared spectral peak assignment of metal ferro-
cyanide complexes.
Adsorption frequencies (cm–1)
Complexes
HOH C≡N HOH
bending Fe-C Metal-N
Mn2[Fe(CN)6]·3H2O3701 2070 1631 592 451
Co2[Fe(CN)6]·2H2O3724 2083 1609 592 465
Ni2[Fe(CN)6]·5H2O3697 2091 1611 592 463
Cu2[Fe(CN)6]·7H2O3845 2090 1621 592 503
Zn2[Fe(CN)6]·3H2O3685 2080 1600 603 496
Cd2[Fe(CN)6] 37242071 1623 590 508
Table 3. Magnetic moments and molar co nductivity of metal
ferrocyanide complexe s.
Metal hexacyanoferrate (II)µcalc (B.M.) µeff (B.M.) Molar conductance
(µS)
Mn2[Fe(CN)6]·3H2O 5.92 6.21 24.2
Co2[Fe(CN)6]·2H2O 3.87 4.36 9.81
Ni2[Fe(CN)6]·5H2O 2.83 2.99 6.61
Cu2[Fe(CN)6]·7H2O 1.73 2.45 6.72
Zn2[Fe(CN)6]·3H2O 0.00 0.81 2.70
Cd2[Fe(CN)6] 0.00 0.90 7.44
Table 4. Major X-ray absorption peaks in the XRD spectra
of manganese ferrocyanide.
2 θ d-Spacing(Å)
observed
Relative intensity
(%)
d-Spacing[Å]
reported in PCPDF
database
17.61555.0348 56.48 5.8087
24.97953.56478 100.00 3.5570
29.67263.0117 7.07 3.0334
39.15842.3005 6.69 2.3081
40.02772.2525 9.91 2.5152
43.40912.0846 5.28 2.9043

C. A. CHUGH ET AL. 25
Table 5. Major X-ray absorption peaks in the XRD spectra
of cobalt ferrocya nide .
2 θ d-Spacing(Å)
observed
Relative Intencity
(%)
d-Spacing[Å]
reported in PCPDF
database
17.7134 5.0072 60.23 5.0300
25.0657 3.5527 100.00 3.5600
35.8547 2.5045 64.74 2.5300
43.7255 2.0702 8.97 2.0800
44.9538 2.0165 13.02 2.2800
Table 6. Major X-ray absorption peaks in the XRD spectra
of nickel ferrocyanide.
2 θ d-Spacing(Å)
observed
Relative intensity
(%)
d-Spacing[Å]
reported in PCPDF
database
17.7146 5.0069 60.93 5.0500
25.0107 3.5604 100.00 3.5700
35.7078 2.5145 53.31 2.5700
40.1426 2.2463 10.26 2.2600
44.0851 2.0542 15.62 2.0600
51.3617 1.7789 10.64 1.7840
54.7539 1.6765 4.39 1.6830
57.9877 1.5891 11.22 1.5230
Table 7. Major X-ray absorption peaks in the XRD spectra
of copper ferrocyanide.
2 θ d-Spacing(Å)
observed
Relative Intencity
(%)
d-Spacing[Å]
reported in PCPDF
database
25.1752 3.5375 79.69 3.5000
29.7271 3.0054 7.41 3.0200
36.0522 2.4913 36.50 2.5000
40.3144 2.2372 14.79 2.2300
44.3532 2.0424 12.34 2.0400
Table 8. Major X-ray absorption peaks in the XRD spectra
of Zinc ferrocyanide.
2 θ d-Spacing(Å)
observed
Relative Intencity
(%)
d-Spacing[Å]
reported in
PCPDF database
16.3677 5.4157 100.00 5.4000
19.7227 4.5014 46.65 4.5100
21.7924 4.0783 90.70 4.0800
28.6684 3.1139 22.18 3.1100
29.7535 3.0027 9.27 3.0000
35.6073 2.5141 10.35 2.5400
37.7830 2.3810 7.67 2.3700
38.8405 2.3186 7.21 2.3200
40.9696 2.2029 11.16 2.2000
47.8545 1.9008 5.80 1.9500
Table 9. Major X-ray absorption peaks in the XRD spectra
of cadmium ferrocyanide.
2 θ d-Spacing(Å)
observed
Relative intensity
(%)
d-Spacing[Å]
reported in
PCPDF database
19.54674.5415 3.45 4.1100
28.70883.1096 19.86 3.1600
31.75562.8178 3.52 2.8300
35.31962.5412 39.74 2.4900
39.65862.2726 19.20 2.2300
42.74672.1153 9.50 2.1100
49.13731.8541 1.50 1.8180
50.79091.7976 7.34 1.7470
57.32441.6073 10.31 1.6670
59.33631.5575 2.77 1.5760
61.42291.5095 1.43 1.5350
66.31951.4094 2.20 1.4740
pension of metal ferrocyanides and two with samea-
mount of distilled water) were placed at equal distance
from center in order to see the effect of metal ferrocya-
nides on the growth of fungal pathogen. Inhibition zones
were measured after 36 hrs of incubation. Dumb bell
shaped growth of fungus was observed in case of metal
complex possesing growth inhibitory component(s).
Food poisoning technique was used to find percent in-
hibition. For this purpose 0.375% (w/v) metal complex
was spread to each petri-dish containing the sterilized
media, while in control treatment equal amount of pure
solvent was added. The fungal plug was placed at the
centre of petri-dish. Growth of fungus was recorded after
72 hrs of incubation. The percent inhibition was calcu-
lated using the formula of Vincent [23].
Percent Inhibition = (C-T)/C  100
Where C is the growth in control in mm and T is growth
in treatment in mm.
All the experiments were carried out in triplicate in
randomized block design and average value was used for
interpretation of results (Tables 5-9).
2.3.1. Correlation Coefficient (r)
The correlation coefficient (r) was calculated using the
following equation,
 

22
22
nxy xy
r
nxxnyy



 


 

 


 
Here n is the number of data points.
1) r = +1, perfect positive correlation, increase in one
variable is accompanied by the increase in the other.
2) r = –1, perfect negative correlation, decrease in one
variable is accompanied by the decrease in the other.
2.3.2. Coefficient of Determination (“r2”)
Although correlation coefficient is a good measure of the

C. A. CHUGH ET AL.
26
strength of the association, but it has got no literal inter-
pretation. The squared values of r, r2 called coefficient of
determination, however have a very clear meaning. It
gives the measure of the proportion of variation in one
variable associated with variations in the other. For ex-
ample, if the value of r = 0.8, then r2 = 0.64. It means
that 64% variations in the value of inhibition zones are
associated with variation in metal complex and the re-
maining 36% can be attributed to some other unknown
factors. The value of r2 ranges from 0 to 1.
2.3.3. Significance Test
The significance test (t test) was performed and values of
was calculated using the formula:

2
2
1
n
tr
r


Here, n is number of observations.
The observed value of “t” is compared with the critical
value of t obtained for n-2 degrees of freedom at 5% sig-
nificance level from the t distribution table [24].
3. Results and Discussion
3.1. Characterization of Metal Ferrocyanides
The molecular formula of synthesized metal complexes
has been established on the basis of elemental analysis
(Table 1) and thermal studies. Assignments of infra red
peaks have been reported in Table 2. A broad band in the
range of 3400 - 3750 cm–1 has been observed due to in-
terstitial water molecules and OH− groups while the
characteristic HOH bending appears at 1600 - 1631 cm–1
in case of all the complexes synthesized. A sharp peak at
2080 ± 10 cm–1 is characteristic of cyanide stretching.
Sharp peaks at 691 - 590 cm–1 are characteristic of Fe-C
stretching frequencies. Metal-Nitrogen was observed at 451 -
508 cm–1.
Values of observed and calculated magnetic moments
have been reported in Table 3. From a structural stand
point, the ferrocyanide ion can be considered to be a
good example of strong field (low spin) octahedral com-
plexes. In the presence of the strongly perturbing cyanide
ligand the 3d orbitals of ferrous ion will get splitted,
causing a relatively large separation between t2g and eg
orbitals. In the ground state, therefore, the six electrons
from Fe (II) ion will be placed in the low lying t2g orbi-
tals. The metal ions like Zn2+, Co2+, Cu2+, Cr3+, Ni2+,
Mn2+ and Cd3+ will remain in the lattice.
All synthesized metal ferrocyanides are expected to be
diamagnetic due to paired electrons. However, the outer
cations may contribute to the observed magnetic moment,
if any. The magnetic moment of Mn, Cu, Co and other
cyanides are diamagnetic as expected. Observed mag-
netic moment values (Table 3) of these metal hexacyan-
oferrates were found to be in good agreement with cal-
culated values. µobs indicate presence of three unpaired
electrons in cobalt ferrocyanide, which is in agreement
with d7 configuration of Co2+, whereas reported value of
magnetic moment for cobalt ferrocyanide is 4.6 BM. µobs
values revealed that five, three, two and one unpaired
electrons are present in Mn(II), Co(II), Ni(II), and Cu(II)
hexacyanoferrates respectively, while zinc and cadmium
hexacyanoferrates have zero magnetic moments.
Conductivity measurements (Table 3) in non a
ferrocyanides and found that zinc and cadmium ferro-
queous
so
were carried out to confirm the
pr
haracterized
by
3.2. Antifungal Potential
etal complexes against M.
pe
per and cadmium ferro-
cy
of correlation coefficient (“r”) and coeffi-
lutions provide a method for testing the degree of ioni-
zation of the complexes. The value of molar conductance
the soluble complexes in DMSO indicate these complexes
to be poor electrolytes.
TG and DTA studies
esence of lattice water in metal hexacyanoferrates. Mass
loss was found to be equivalent to three, two, five, seven,
and three moles of water in case of Mn(II), Co(II), Ni(II),
Cu(II), and Zn(II) hexacyanoferrate respectively. Cad-
mium ferrocyanide did not show any loss of water mole-
cule. Molecular formula determined on the basis of ele-
mental analysis, TG and DTA are as follows:
Mn2[Fe(CN)6]·3H2O, Co2[Fe(CN)6]·2H2O,
Ni2[Fe(CN)6]·5H2O, Cu2[Fe(CN)6]·7H2O,
Zn2[Fe(CN)6]·3 H2O, and Cd2[Fe(CN)6].
The synthesized metal complexes were c
X ray diffraction studies (Figure 1-6). d values of the
observed peaks have been reported in Table (5-9) which
are in good agreement with the published data for man-
ganese, cobalt, nickel, copper, zinc and cadmium fer-
rocyanides in PC-PDF file numbers 46-0910, 23-0188,
14-0291, 01-0244, 24-0164, and 01-0433 respectively.
Antifungal potential of m
rniciosa and V. fungicola has been reported in Table 10.
Manganese, nickel, copper and zinc ferrocyanides have
exhibited inhibition zones in the range of 2 - 4 mm with
percent inhibition ranging 30% - 60% against M. pernici
osa. Nickel ferrocyanide possesses maximum inhibitory-
effect against wet bubble causing pathogen M. perniciosa
showing 60% growth inhibition.
Manganese, cobalt, nickel, cop
anide have exhibited inhibition zone ranging 2 - 18
mm and percent inhibition in the range of 4% - 85%
against V. fungicola. Cadmium ferrocyanide has been
found to be most effective against V. fungicola showing
85% growth inhibition. All the metal ferrocyanides ex-
cept zinc ferrocyanide exhibit significant activity against
V. fungicola.
The values

C. A. CHUGH ET AL.
27
Figure 1. X-ray diffraction pattern for manganese ferrocyanide.
Figure 2. X-ray diffraction pattern for cobaltferrocyanide.
Figure 3. X-ray diffraction pattern for nickel ferrocyanide.

C. A. CHUGH ET AL.
28
Figure 4. X-ray diffraction pattern for copper ferrocyanide.
Figure 5. X-ray diffraction pattern for zinc ferrocyanide.
Figure 6. X-ray diffraction pattern for cadmium ferrocyanide.

C. A. CHUGH ET AL.
29
able 10. Antifungal activity o
Fungal pathogen
Mycogoneperniciosa
Fungal pathogen Verticel-
liumfungicola
Tf transition metal ferrocya-
nides.
Metal ferrocyanides
m) inhibition
Inhib
zone (mm)
t
inhibition
Inhibition Percent
zone (m
ition Percen
Mn2[Fe(CN)6]·3H2O 2 30 7 32
Co2[Fe(CN)6]·2H2O 0 00 8 38
Ni2[Fe(CN)6] ·5H2O 4 60 2 5
Cu2[Fe(CN)6]·7H2O 3 50 15 75
Zn2[Fe(CN)6]·3H2O 2 30 - -
Cd2[Fe(CN)6] 0 00 17 85
The values of correlation fficient (“r”) and coeffi-
ci 2
iversity Grant Commi
ind Ballabh Pant University
A. El-Sayed, A. A. Shabana, M. M. Abo-Alyand and
M. M. Sallam, “Electrical Transport as a Function of Tem-
perature in Hlexes,” Journal of
materials Scieonics, Vol. 14, No.
coe
ent of determination (“r”) are 0.997 and 0.994 respec-
tively for observations related to the inhibitory effect
against M. perniciosa. The value of “r2” suggests that
99.4% inhibition was caused by metal ferrocyanides and
rest 0.6% may be attributed to other unknown and un-
controlled factors. The calculations related to the signifi-
cance test (“t” test) revealed that the value of “t” (25.73)
is much higher than the critical value noted from “t” dis-
tribution table for degree of freedom 4 at 5% significance
level. This suggests that there are less than 5% chances
of error in drawing the conclusions.
The calculated value of “r”, “r2”, and “t” (at 5% sig-
nificance level), for the observations made in case of V.
fungicola are 0.999, 0.998 and 51.50 respectively. The
value of “t” is much higher than the critical value which
is indicative of less than 5% chances of occurrence of
error, and that the null hypothesis may be safely rejected
at 5% significance level.
There are few reports on synergistic effect of antimicro-
bial activity of metal ferrocyanide with botanicals [13].
These complexes have also been reported to adsorb bio-
molecules. Hence these may be proved to be potential
solid support for plant based biocidal component(s). There
may be the possibility of adsorption of active ingredi-
ent(s) at the surface of transitional metal ferrocyanides.
Thus concentration, efficiency and shelf life of active
chemical(s) may increase and lead to increased activity
(biopotentiation). These studies will be helpful in devel-
opment of new fungicidal formulations for management
of dry and wet bubble diseases of button mushroom.
4. Acknowledgements
The author is thankful to Unssion,
New Delhi, India for providing financial support (F. No.
34-346\2008 SR) and Department of Plant Pathology,
of Agriculture and Technology, Pantnagar, Uttarakhand,
India, for providing fungal cultures for present investiga-
tion.
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