Antifungal Potential of Transition Metal Hexacyanoferrates against Fungal Diseases of Mushroom

doi:10.4236/ojsta.2012.13005

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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

Email: [email protected]

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. A. CHUGH ET AL.

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,

 



nxy xy

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.

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:







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

were carried out to confirm the

haracterized

3.2. Antifungal Potential

etal complexes against M.

per and cadmium ferro-

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.

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.

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.

able 10. Antifungal activity o

Fungal pathogen

Mycogoneperniciosa

Fungal pathogen Verticel-

liumfungicola

Tf transition metal ferrocya-

nides.

Metal ferrocyanides

m) inhibition

Inhib

zone (mm)

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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