Antifungal activities of ketoazomethines of phenyl glyoxal and p-substituted anilines

Article abstract of DOI:10.1155/2011/732197

A new series of ketoazomethines were synthesized by condensation of phenyl glyoxal (prepared by partial oxidation of acetophenone) with various p-substituted anilines viz. p-Cl, p-Br, p-NO₂, p-(C₂H ₅)₂N and p-CH

Full text of DOI:10.1155/2011/732197

ISSN: 0973-4945; CODEN ECJHAO
E-Journal of Chemistry
2011, 8(1), 59-62
http://www.e-journals.net
Antifungal Activities of Ketoazomethines of
Phenyl Glyoxal and p-Substituted Anilines
*
VISHNU VATS, R.K. UPADHYAY and PRATHIBHA SHARMA
Department of Chemistry, N.R.E.C College
Chaudhary Charan Singh University, Meerut, India
*
Department of Plant Pathology
Indian Agricultural and Research Institute, New Delhi, India
vatsvish_2006@yahoo.co.in
Received 16 February 2010; Accepted 22 April 2010
Abstract: A new series of ketoazomethines were synthesized by condensation
of phenyl glyoxal (prepared by partial oxidation of acetophenone) with various
p-substituted anilines viz. p-Cl, p-Br, p-NO2, p-(C H ) N and p-CH These
2
5 2
3.
1
compounds were characterized by elemental analysis, IR and H NMR. The
synthesized ketoazomethines were screened for their antifungal activity against
hazardous fungi namely Fusarium oxysporum, Alternaria brassicola,
Sclerotium and Pythium.
Keywords: Ketazomethines, Synthesis, Antifungal activity.
Introduction
1
Schiff’s bases and their complexes obtained by reactions with transition metals are well
2
, 3
4
known for their antibacterial , antineoplastic , antiviral , anti-inflammatory activity and
5
6,7
8-10
11-12
are used to design medicinal compounds . Many researchers studied the synthesis
13-17
characterization and structure activity relationship of Schiff’s bases
,
. The present study
includes synthesis of a new series of ketoazomethines obtained by condensation of phenyl
glyoxal with p-substituted anilines viz. p-Cl, p-Br, p-NO etc. and examine their antifungal
2
activity against hazardous fungi i.e. Fusarium oxysporum, Alternaria brasssicola,
Sclerotium and Pythium which causes harm to crops like tomato, onion, cauliflower,
broccoli etc.
Experimental
All the chemicals used were either E-Merck or Qualigens. Melting points of all the
compounds determined in open glass capillaries were uncorrected. Elemental analysis of
samples was carried out on Euro EA elemental analyzer. Infrared spectra were recorded in

6
0
PRATHIBHA SHARMA et al.
KBr medium on Thermo Nicollet Nexus FT-IR spectrophotometer and 300MHz NMR
spectra were recorded in dimethylsulphoxide medium on Varian C-13 NMR spectrometer
using TMS as internal standard. Column chromatography was carried out using silica gel
(
finer than 200#).Characterization data is presented in Table 1 and spectral data in Table 2.
Table 1. Physical characteristics and elemental analysis of ketoazomethines
Analysis
M P
Compd
M.F
Color
0
C %
H %
N%
C
Calcd. Found Calcd. Found Calcd.Found
4
4
4
A
B
C
C H NOCl Light pink 151 68.85 68.65
10
4.09 4.01 5.73 5.34
3.47 3.16 4.86 5.10
3.93 3.92 11.02 11.1
5.26 4.81 6.69 6.80
7.14 7.31 10.00 9.84
5.82 6.08 6.27 6.23
14
C H NOBr Pale yellow 163 58.33 58.29
10
14
C H N O
Green
187 66.14 66.12
14
10
11
2
3
4
D
C H NO Light brown 170 80.38 80.20
1
4
4
E
F
C H N O Scarlet Red 161 77.14 77.67
14 15 2
4
C H NO
1
Brown
180 80.71 80.60
5
13
Table 2. Spectral data of ketoazomethines
νC=O Benzene ring
chain νC−H νC=C
δC−H δC−H Subs. Gps
freq.
NMR
(300 MHz)
Compd.
νC=N
(2H) (5H)
1
646
br
δ2.5(d,2H),
C H NOCl 1626 3012 1475
1
825
696
608 (νC−Cl)
4
10
δ6.51(s,5HAr-H),
δ3.38(s,1H,CH-
N),δ6.44(s,4H,Ar
H),δ1.12(3H,CH3)
C H NOBr 1671 3023 1494 1589 811
1
780
502
4
10
7
6
53,
96
1304, 1578
C H N O 1634 2990 1476 1590 838
1
4
10
2
3
νC−NO2)
1
1
1
498,
444
755,
695
752,
688
C H NO 1670 3055
11
1593
-
-
14
1
510,
453
1453 (δCH2),
1354 (δCH3)
C H NO 1672 3074
15
1593 815
1560 826
14
1
560,
479
C H NO 1630 3029
13
709
1357(δCH3)
15
1
Preparation of phenyl glyoxal
Phenyl glyoxal was prepared by the partial oxidation of acetophenone with selenium
dioxide. Reaction mixture containing acetophenone (0.1 mol,1) and selenium dioxide
(
0.1 mol) in round bottom flask containing 95% ethyl alcohol was refluxed for 4-6 h.
Orange yellow reaction mixture was decanted and concentrated over water bath and
dissolved in ether to remove selenium from the product.
Preparation of ketoazomethines(4a-f) (Scheme 1)
Phenyl glyoxal (2, 0.2 mol) and aniline (3A-F, 0.2 mol) were taken in a round bottom flask
containing 100 mL of ethanol and refluxed on water bath for 8 h. Excess of ethanol was
removed from reaction mixture and cooled at room temperature. Then it was poured in ice
cold water and filtered. Solid obtained were collected and recrystallized with ethanol.

Antifungal Activities of Ketoazomethines
61
Scheme 1
Antifungal activities
Preparation of medium and sample solutions
For the preparation of PDA (Potato Dextrose Agar) medium 250 g potato pieces boiled in
water were filtered and filtrate was made up to 1 liter. To this solution 20 g dextrose powder
was added followed by heating to a syrupy viscous consistency. Standard solutions of all the
samples of 50 ppm concentration were prepared by dissolving known quantity of
compounds in known volume of DMSO (dimethylsulphoxide).
18
Antifungal activities were performed by paper disc method . First of all PDA medium
was sterilized in Autoclave and then poured into autoclaved Petri dishes near the gas flame,
to avoid contamination and these plates were placed in Laminar Air Flow for an hour. There
after filter paper discs dipped in sample solution were placed on medium in Petri dish and
kept in Laminar Air Flow for half an hour. Fungus bit of 1mm diameter was put at a distance
of 1 cm from paper disk wet in sample solution and Petri dishes were sealed with paraffin
0
film in incubator at 25-30 C for 72-96 h for growth of fungus. Fungal growth was measured
as the mean of distances from inoculation point of fungus to its maximum growth in three
directions. Three replicates were used for each fungus.
The synthesized compounds were subjected to antifungal screening and compared
against a standard fungicide Diethane M-45 and DMSO as control with no inhibition; results
are given in Table 3.
Table 3. Results of inhibition of synthesized ketoazomethines
Inhibition.
Time, days
Compd.
S
P
F.O.
A. B.
C H NO
1
3
3
3
3
3
3
3
++
++
++
+
+
++
+
+
+
+
++
++
++
-
4
11
C H NOBr
10
14
C H NOCl
10
++
++
-
14
C H N O
3
++
-
+
14
10
2
C H NO
5
+
-
1
13
C H N O
15
-
-
1
4
2
Diethane-M45
-
-
+
+
S.- Sclerotium, P.-Pythium, A.B. -Alternaria Brassicola, F.O.-Fusarium Oxysporum, -Ve-1-7mm, +Ve-
-14mm, ++Ve-15-20 mm
7

6
2
PRATHIBHA SHARMA et al.
Results and Discussion
The antifungal studies of the compounds were tested by paper bit method against hazardous
fungi namely Fusarium Oxysporum, Alternaria Brassicola, Pythium and Sclerotium and
were compared to reference fungicide Diethane-M45, p-chloroanil showed highest inhibition
against Fusarium oxysporum, Sclerotium and Alternaria brassicola, p-bromoanil was
effective against Pythium, Sclerotium and Alternaria brassicola while phenylanil was
effective against Sclerotium, p-nitroanil was effective against Pythium, Alternaria brassicola
and Fusarium oxysporum.
Acknowledgment
We are grateful to the staff of Plant Pathology department of Indian Agricultural Research
Institute, New Delhi and IIT Roorke for their immense support to accomplish the project.
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