Study of mesoionic compounds: Synthesis and pharmacological evaluation of several 2-[{(4-Substituted-1-sulphonyl) Sydnon-3-yl}]-1,3,4-thiadiazino(6,5-b) indoles as antimicrobial, insecticidal and antihelmintic agents

Article abstract of DOI:10.13005/ojc/300134

In the present study several novel 2-[{(4-Substituted-1-sulphonyl)sydnon-3- yl}]-1, 3, 4-thiadiazino(6, 5-b) indoles [4a-f] synthesised from 2-amino-1, 3, 4-thiadiazino (6, 5-b) indole. Structures of the synthesized substituted indoles were characterized

Full text of DOI:10.13005/ojc/300134

ISSN: 0970-020 X
CODEN: OJCHEG
2014, Vol. 30, No. (1):
Pg. 271-278
ORIENTAL JOURNAL OF CHEMISTRY
An International Open Free Access, Peer Reviewed Research Journal
www.orientjchem.org
Study of Mesoionic Compounds: Synthesis and
Pharmacological Evaluation of Several 2-[{(4-Substituted-1-
sulphonyl) Sydnon-3-yl}]-1,3,4-thiadiazino(6,5-b)indoles as
Antimicrobial, Insecticidal and Antihelmintic Agents
RANJANA DUbEY1, NIDHI CHAUDHARY2, RAvINDRA KUMAR3 and HAMENT PANwAR3*
1Department of Chemistry, S.R.M. University, Modinagar - 201204, Ghaziabad, India.
2Department of Chemistry, M.I.E.T., Meerut - 250 001, India.
3Department of Chemistry, Neelkanth Institute of Technology, Modipuram - 250 110, Meerut, India.
*Corresponding author E-mail: dr_h.panwar@rediffmail.com
http://dx.doi.org/10.13005/ojc/300134
(Received: December 20, 2013; Accepted: January 10, 2014)
AbSTRACT
In the present study several novel 2-[{(4-Substituted-1-sulphonyl)sydnon-3-yl}]-1,3,4-
thiadiazino(6,5-b) indoles [4a-f] synthesised from 2-amino-1,3,4-thiadiazino (6,5-b) indole.Structures
1
of the synthesized substituted indoles were characterized by IR, H-NMR, Mass and elemental
analysis (C, H, N). Synthesised indole derivatives were screened for antimicrobial, insecticidal and
anthelmintic activities. Compound 4a displayed significant biological spectrum.
Key words: Antimicobial, insecticidal, antihelmintic, sydnones, indoles.
INTRODUCTION
member of the mesoionic category of compounds.
Withfewexceptions, sydnonesarestablecompounds
and display significant polarity. Sydnones are
reported to posses anticonvulsant4, antitumor5,
diuretic6, antimicrobial7-9, hypotensive10, anticancer11,
analgesic12, insecticidal13 and antihelmintic14 activities.
On the other hand, indole and its analogs showed
versatile biological spectrum as anti-inflammatory15-
20, anticonvulsant21, antitumor22, antimicrobial23,
antibacterial24-25, antifungal26 and antihelmintic27.
In continuation of research work28-29, we focused
our efforts on the synthesis of 2-[{(4-Substituted-
1-sulphonyl)sydnon-3-yl}]-1,3,4-thiadiazino(6,5-b)
An enormous amount of research
on synthetic and pharmacological studies of
sydnones has been reported during the last few
decades1.Mesoionic compounds are non-benzenoid
heterocycles containing different combination
of hetero atoms. Sydnones being mesoionic
compounds, are 1, 2, 3-oxadiazolium-5-olates
and their chemistry has been widely studied by
the scientific workers2-3 due to their electronic and
versatile biological profile. Literature is evident to
reveal that sydnone derivatives are most important

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DUbEy et al., Orient. J. Chem., Vol. 30(1), 271-278 (2014)
indoles 4a-f starting from 2-amino-1, 3, 4-thiadiazino radical from ion [q]+ furnish ion [r]+ (Table-1).
(6, 5-b) indole (Scheme-1). Hence all these
observation prompted us to synthesis some novel Pharmacology
derivatives of indoles bearing syndnone moiety. It
Compounds 3 and 4a-f were evaluated for
was interesting to study the biological behaviours of antimicrobial, insecticidal and antihelmintic activity
various substituted sydnones.
RESULTS AND DISCUSSION
(Table-2, 3 & 4).
Antimicrobial screening
All the newly synthesized compounds
Synthetic strategy has been outlined in 3 and 4a-f were screened for their antibacterial
Scheme-1. Compound 1 and 2 were synthesised and antifungal activity. All the bacterial as well
by our earlier reported method29. The condensation as fungal strains were clinical isolates, identified
reaction of compound 2 and chloro sulphonic acid with conventional morphological and biochemical
in presence of catalytic amount of phosphorous methods.The microorganisms employed antibacterial
pentoxide yielded the compound 3.The formation of studies were Staphylococcus aureus, E. coli and
compound 3 was evidenced by the disappearance Klabsiella pneumoniae. Disk diffusion method30-
1
31
of singlet in H-NMR spectra and IR spectral
was used for determination of the preliminary
band at d 4.69 ppm and 3106 cm-1 respectively. antibacterial activity. Disks measuring 6.25 mm in
It was further evidenced by the appearance of IR diameter were punched from Whatman no. 1 filter
spectral band at 1180 cm-1 due to the SO2 group. paper.batches of 100 disks were dispensed to each
The desired derivatives, 4a-f were obtained by the screw-capped bottle and sterilized by dry heat at 140
reaction of compound 3 and secondary amines. °C for an hour. The test compounds were prepared
1
In H-NMR spectra compounds 4, the peaks were with different concentrations using DMF.One milliliter
observed at d 2.02-2.51 due to hydrogens of containing 100 times the amount of chemical in each
morpholine ring. Presence of absorption band at disk was added to each bottle, which contained
1460, 1120 for C-O-C of morpholine ring cleared the 100 disks. Disks of each concentration were for
synthesis of derivatives 4a-f.Scheme-2 explored the placed in triplicate in nutrient agar medium seeded
general mass fragmentation of 2-[{(4-morpholino- with fresh bacteria separately. The incubation was
1-sulphonyl) sydnon-3-yl}]-1,3,4-thiadiazino(6,5-b) carried out at 37 °C for 24 h.Ampicillin trihydrate and
indoles 4a.In the mass spectra of compound 4a, the fluconazole were used as standard drugs. Solvent
molecular ion peak 420 [M+] (15%) also confirmed and growth controls were kept and zones of inhibition
the formation of the sydnonyl substituted indoles. were noted. The bacterial inhibition values (mm) of
The molecular, base peak and other peak with their the tested compounds against the tested bacterial
relative intensities were summarised in Table 1.The strains are recorded in Table 2. On the other hand,
mass spectral study of sydnonyl substituted indoles the newly prepared compounds were screened for
publicized that parent compound 4a cleaved and their in vitro antifungal activity against Aspergillus
released gradually fragment radicals and neutrals by fumigatus (plant isolate), Candida albicans and
following two routes viz route A and route b. Route Candida glabrata, in DMF by the serial plate dilution
A produced two daughter ions [a]+ and [b]+ while method32-33.Sabouraud’s agar media were prepared
route b also produced two daughter ions [n]+ and by dissolving peptone (1 g), D-glucose (4 g), and agar
[o]+. Ion [a]+ releases N2 radical to give ion [c]+ which (2 g) in distilled water (100 ml) and adjusting the pH
further expel out S radical to yield quinolinium ion to 5.7.Normal saline was used to make a suspension
[d]+.Quinolinium ion28 [d]+ splits to give ion [e]+.In ion of the spore of fungal strain for lawning. A loopful of
[b]+, sydnonyl ring ruptures similarly to that of other particular fungal strain was transferred to 3 ml saline
pattern of sydnone derivatives29 to yield two ions, ion to get a suspension of the corresponding species.
[f]+ and [j]+. Ion [f]+ further cleaved into ions [g]+ and Agar media (20 ml) was poured into each petri dish.
[s]+ . Ion [g]+ transformed into ions [h]+ and[i]+. Ion [j]+ Excess suspension was decanted and the plates
breaks down to give ions [k]+ and[l]+ and SO2 release were dried by placing in an incubator at 37 °C for 1
converted ion [l]+ into ion [m]+. Ions [p]+ and[q]+ were h. Using an agar punch wells were made into each
obtained by the splitting of ion [n]+. Expulsion of NO well labelled.A control was also prepared in triplicate

DUbEy et al., Orient. J. Chem., Vol. 30(1), 271-278 (2014)
273
and maintained at 37 °C for 3–4 days. Antifungal
activity was determined by measuring the diameter
of the inhibition zone.The fungicidal inhibitory (mm)
values of the tested compounds against the tested
fungal species are recorded in Table- 2.
apparatus (Campbell Electronics, Mumbai, India)
and are uncorrected. The homogeneity of all the
newly synthesized compounds were routinely
checked byTLC on silica gel G plates and spots were
located by using iodine chamber.Elemental analysis
was performed in Heraeus CHN rapid analyser.The
results were found within the 0.4% of theoretical
values.Infrared spectra were recorded on Kbr pellets
on a Perkin Elmer system 2000 FTIR spectrometer
and 1H- NMR spectra on bruker DPX 200 usingTMS
as internal standard.
Insecticidal activity
Periplaneta americana was taken for
insecticidal study and 1 and 2% solutions of the
derivatives 3 and 4a-f were injected in the abdominal
of P. americana with the help of micro syringe.
The time of death had been noted as KD (Knock
promising to moderate activity) value.Cypermethrin
was used as standard drug. At the time of death the
antennae of P. americana became motionless, the
appendages shrunk and folded towards the ventral
side and cockroach lay dorsally34 (Table- 3).
Synthesis
Synthesis of 2-(1,3,4-thiadiazino (6, 5-b)indole-
2´-yl)aminoacetic acid (1)
A mixture of 2-amino-1, 3, 4-thiadiazino
(6, 5-b) indole (0.01 mol), chloroacetic acid (0.01
mol) and anhydrous K2CO3 (5.0 gm) in methanol
(dry, 80 ml) were refluxed for about 18 h on a water
bath. On completion of the reaction, the excess of
solvent was distilled off under reduced pressure. At
0-5 °C, 40% hydrochloric acid (0.01 mol) added to
residue and a solution of sodium nitrite (0.01 mol) in
water (25 ml) was added drop wise during 30 min.
The reaction was allowed to stand overnight. Crude
reaction mixture was filtered, washed thoroughly
with ice cold water and dried in air. The solid thus
obtained was recrystallised with ethanol- water to
obtain compound 1:yield 68%, m.p.160 °C.IR (Kbr)
νmax in cm-1: 1548 (C C of aromatic), 1568 (N=O),
1615 (C=N), 1710 (C=O of COOH), 2837 (CH2),
3010 (OH of COOH), 3047 (aromatic CH). 1H-NMR
(CDCl3) d:4.69 (d, 2H, CH2), 6.50-6.80 (m, 4H, ArH),
9.60 (s, 1H, COOH, exchangeable with D2O). MS:
m/z 289 [M]+. Elemental analysis (C11H7N5SO3),
calcd: C 45.67, H 2.42, N 24.22%, found: C 45.70,
H 2.40, N 24.45%.
Anthelmintic activity
Indian adult earthworms (Pheretima
posthuma) were collected from moist soil and
washed with normal saline to remove all faecal
matter and used for the anthelmintic activity. All the
synthesized derivatives 3 and 4a-f were dissolved
in minimum amount of DMF and the volume
adjusted to 10 ml with saline water. All solutions of
synthesized derivatives and drugs solutions were
freshly prepared. Groups of six earthworms were
released into desired formulations and the paralytic
and lethal time noted. Albendazole was used as
standard drug.Observations were made for the time
taken for paralysis and death of individual worms.
Paralysis was said to occur when the worms did not
receive even in normal saline. Death was concluded
when the worms lost their motility followed by fading
away of their body colour35-38 (Table- 4).
EXPERIMENTAL
Synthesis of 2-(Sydnon-3´-yl)-1, 3, 4-thiadiazino
(6,5-b)indole (2)
All the chemicals used for the preparation
of desired derivatives, were obtained from Sisco
Research Laboratories (SRL), Mumbai, India;
Qualigen Fine Chemicals, Mumbai, India; E. Merck
Ltd., New Delhi, India.The reference drugs ampicillin
trihydrate,fluconazole,cypermethrinandalbendazole
were procured from Ind-Swift, Pharmaceutical,
Panjab; Savorite Pharmaceuticals, Gujarat; Royal
Crop Science, Panipat, India. The melting points
of the compounds were determined in open glass
capillaries with the help of thermonic melting points
Compound 1 was heated with acetic
anhydride (1:5 by weight) on a water bath for 3 h.
The reaction mixture was poured over crushed ice
and recrystallised with ethanol to get compound 2:
yield 62%, m.p.136 °C.IR (Kbr) νmax in cm-1:841(N-O
of sydnones), 1092 (C-O of sydnone), 1252 (C-N),
1522 (N-N), 1573 (C C of aromatic), 1620 (C=N),
1752 (C=O of sydnone), 3033 (aromatic CH), 3106
1
(sydnone -CH). H-NMR (CDCl3) d: 4.69 (s, 1H,
sydnone), 6.62-6.90 (m, 4H, Ar-H). MS: m/z 271

274
DUbEy et al., Orient. J. Chem., Vol. 30(1), 271-278 (2014)
Table 1: Mass spectral data 2-[{(4-Morpholino-1-sulphonyl)
sydnon-3-yl}]-1,3,4-thiadiazino(6,5-b)indoles 4a
Selected ions
[M]+
[a]+
[b]+
[c]+
[d]+
[e]+
[f]+
[g]+
[h]+ [i]+
m/z
420
15
186
46
[k]+
150
79
234
37
154
50
[m]+
270
43
122
40
[n]+
150
79
96
61
[o]+
162
100
233
41
[p]+
108
25
84
64
[q]+
78
13
40
12
[r]+
150
79
204
30
Relative intensity (%)
Selected ions
m/z
[j]+
54
[l]+
86
Relative intensity (%)
22
80
Table 2: Antimicrobial screening of 2-[(4-Sulphoyl chloride)sydon-3-yl]-1,3,4-thiadiazino(6,5-b)
indoles 3 and 2-[{(4-substituted-1-sulphonyl)sydnon-3-yl}]-1,3,4-thiadiazino(6,5-b) indoles 4a-f
Compound
Antibacterial activity (mm)
Antifungal activity (mm)
S. aureus
E. coli K. pneumoniae A. fumigatus C. albicans C. glabrata
3.
4a.
4b.
4c.
-
10
-
-
15
6
5
20
10
8
-
16
8
-
10
6
-
-
12
-
-
-
6
6
4d.
4e.
4f.
-
5
-
16
-
-
6
10
6
16
-
-
6
10
8
20
-
-
10
8
14
-
20
-
6
6
-
-
15
-
8
10
8
-
15
-
Ampicillin trihydrate
Fluconazole
DMF (control)
- means no activity.
Table 3: Insecticidal activity of 2-[(4-Sulphoyl
chloride)sydon-3-yl]-1,3,4-thiadiazino(6,5-b)
indoles 3 and 2-[{(4-substituted-1-sulphonyl)
sydnon-3-yl}]-1,3,4-thiadiazino(6,5-b)indoles
4a-f at two different concentrations
(KD value in min.)
Table 4: Anthelmintic activity of 2-[(4-Sulphoyl
chloride)sydon-3-yl]-1,3,4-thiadiazino(6,5-b)
indoles 3 and 2-[{(4-substituted-1-sulphonyl)
sydnon-3-yl}]-1,3,4-thiadiazino(6,5-b)indoles
4a-f against Pheretima posthuma
(paralytic and lethal time in min.)
Comp.
Time [min.]
Comp.
Paralytic time
(min.)
Lethal time
(min.)
1%
2%
3.
4a.
4b.
4c.
4d.
4e.
4f.
12
6
20
10
24
20
15
18
16
8
3.
4a.
4b.
4c.
4d.
4e.
4f.
28
8
22
6
8
12
8
10
12
5
18
13
10
14
12
5
15
18
14
12
19
7
Albendazole
Cypermethrin

DUbEy et al., Orient. J. Chem., Vol. 30(1), 271-278 (2014)
275
[M]+. Elemental analysis (C11H5N5SO2), calcd: C CH).1H-NMR (CDCl3) d:6.57-6.95 (m, 4H, Ar-H).MS:
48.70, H 1.84, N 25.83%, found: C 48.76, H 1.86, N m/z 369.5 [M]+.Elemental analysis (C11H4N5S2O4Cl),
25.80%.
calcd: C 35.72, H 1.08, N 18.94%, found: C 35.61,
H 1.09, N 18.80%.
Synthesis of 2-[(4-Sulphoyl chloride)sydon-3-yl]-
1,3,4-thiadiazino(6,5-b) indoles (3)
General preparation of 2-[{(4-Substituted-1-
Compound 2 (0.01 mol) taken in small sulphonyl)sydnon-3-yl}]-1,3,4-thiadiazino (6,5-b)
portion to the mixture of chloro sulphonic acid indoles (4a-f)
(0.01 mol) and catalytic amount of phosphorous
A mixture of dimethyl formamide and
pentoxide. Shake well to ensure thorough mixing. various 2º-amine (0.02 mol) was added to compound
The resulting mixture heated at 60-65 0C for about 3 (0.02 mol) with stirring for 2 hr. Catalytic amount of
1 hr. On completion the reaction, reaction mixture pyridine was added to reaction mixture.The reaction
allowed to cool and pour the mixture over ice.Stirred, mixture was poured to the ice cold water. Crude
filtered, washed and dried to get compound 3.yield products were recrystallized in appropriate solvents
69%, m.p.194 °C. IR (Kbr) νmax in cm-1: 845(N-O of to furnish compounds 4a-f.
sydnones), 1090 (C-O of sydnone), 1180 (SO2),
1247 (C-N), 1526 (N-N), 1570 (C C of aromatic),
4a:yield 69%, m.p.194 °C. IR (Kbr) νmax in
1625 (C=N), 1749 (C=O of sydnone), 3030 (aromatic cm-1:845 (N-O of sydnones), 1090 (C-O of sydnone),
1180 (SO2), 1247 (C-N), 1526 (N-N), 1570 (C C of
aromatic), 1625 (C=N), 1749 (C=O of sydnone),
3030 (aromatic CH). 1H-NMR (CDCl3) d: 2.02-2.51
(t, 8H, -N-CH2), 6.52-7.00 (m, 4H, Ar-H). MS: m/z
420.10 [M]+. Elemental analysis (C15H12N6S2O5),
N
N
NH2
S
N
a
calcd: C 42.86, H 2.86, N 20.00%, found: C 42.97,
N
N
NO
H 2.82, N 19.97%.
NCH2COOH
S
1
N
4b:yield 51%, m.p.132 °C. IR (Kbr) νmax in
cm-1:851 (N-O of sydnones), 1097 (C-O of sydnone),
1182 (SO2), 1253 (C-N), 1530 (N-N), 1576 (C C of
aromatic), 1631 (C=N), 1742 (C=O of sydnone),
b
N
N
N
O
N
1
S
3031 (aromatic CH). H-NMR (CDCl3) d: 1.83 (s,
2
N
c
O-
1H, NH), 2.10-2.62 (t, 8H, -N-CH2), 6.60-7.12 (m,
4H, Ar-H). MS: m/z 419.10 [M]+. Elemental analysis
(C15H13N7S2O4), calcd: C 42.95, H 3.10, N 23.38%,
found: C 42.91, H 3.12, N 23.46%.
H
N
N
N
O
N
S
3
N
O-
4c:yield 48%, m.p.159 °C. IR (Kbr) νmax in
cm-1:849 (N-O of sydnones), 1094 (C-O of sydnone),
1184 (SO2), 1250 (C-N), 1533 (N-N), 1573 (C C of
aromatic), 1628 (C=N), 1747 (C=O of sydnone),
3028 (aromatic CH). 1H-NMR (CDCl3) d: 2.06-2.69
(t, 10H, -N-CH2), 6.60-7.12 (m, 4H, Ar-H). MS: m/z
418.23 [M]+. Elemental analysis (C16H14N6S2O4),
calcd: C 45.91, H 3.35, N 20.10%, found: C 45.88,
H 3.36, N 20.15%.
S
O
O
d
Cl
N
N
N
O
N
S
N
O-
4a-f
O
S
O
N
X
X = O, NH, CH2, N-CH3, N-C6H5,N-CH2.CH3
4d:yield 57%, m.p.168 °C. IR (Kbr) νmax in
cm-1:854 (N-O of sydnones), 1092 (C-O of sydnone),
1180 (SO2), 1251 (C-N), 1536 (N-N), 1572 (C C of
aromatic), 1637 (C=N), 1740 (C=O of sydnone),
a = i.ClCH2COOH, ii. NaNO2/HCl; b = i. (CH3COO)2O; c = ClSO3H; d = secondary amines
Scheme 1:

276
DUbEy et al., Orient. J. Chem., Vol. 30(1), 271-278 (2014)
1
3033 (aromatic CH). H-NMR (CDCl3) d: 1.22 (s,
3H, N-CH3), 2.15-2.66 (t, 8H, -N-CH2), 6.60-7.12 (m,
4H, Ar-H). MS: m/z 433.41 [M]+. Elemental analysis
(C16H15N7S2O4), calcd: C 44.30, H 3.46, N 22.61%,
found: C 44.27, H 3.40, N 22.69%.
calcd: C 50.89, H 3.43, N 19.79%, found: C 50.87,
H 3.44, N 20.02%.
4f:yield 60%, m.p.182 °C. IR (Kbr) νmax in
cm-1:853 (N-O of sydnones), 1090 (C-O of sydnone),
1185 (SO2), 1255 (C-N), 1533 (N-N), 1570 (C C of
aromatic), 1636 (C=N), 1743 (C=O of sydnone),
3030 (aromatic CH). 1H-NMR (CDCl3) ν: 1.34 (t, J =
6 Hz, 3H, -CH3), 2.78 (q, J = 4 Hz, 2H, -CH2-), 2.10-
2.60 (t, 8H, -N-CH2), 6.60-7.12 (m, 4H, Ar-H). MS:
m/z 447.18 [M]+.Elemental analysis (C17H17N7S2O4),
calcd: C 45.61, H 3.80, N 21.91%, found: C 45.67,
H 3.75, N 22.00%.
4e:yield 52%, m.p.147 °C. IR (Kbr) νmax in
cm-1:848 (N-O of sydnones), 1095 (C-O of sydnone),
1178 (SO2), 1250 (C-N), 1530 (N-N), 1574 (C C of
aromatic), 1630 (C=N), 1744 (C=O of sydnone),
3035 (aromatic CH). 1H-NMR (CDCl3) d: 2.10-2.60
(t, 8H, -N-CH2), 6.79-7.52 (m, 9H, Ar-H). MS: m/z
495.12 [M]+. Elemental analysis (C21H17N7S2O4),
N
N
A
N
O
N
S
O -
N
B
O
O
S
4a
(m/z 420)
N
O
Route A
Route B
N
O
SO2
N
N
N
N
N
N
O
N
O-
N
N
S
O
S
O
N
S
N
O-
a
(m/z 186)
O
m
(m/z 270)
n
N
-NO
(m/z 150)
-N2
O
b
(m/z 234)
O
N
C
S
O
N
N
S
O
O
O
N
O-
N
N
S
c
(m/z 154)
N
O
O
N
N
p
(m/z 108)
-S
o
(m/z 162)
i
(m/z 204)
-NO
O
C
S
N=C-C=O
O
O
N
q
(m/z 78)
N
d
(m/z 122)
f
(m/z 233)
O
SO2
-CN
O
N
N
O
N
C
-SO2
j
(m/z 54)
O
O
k
(m/z 150)
l
e
(m/z 96)
O
SO2
(m/z 86)
N
N
N
g
(m/z 84)
-N2O
O
O
r
(m/z 150)
h
(m/z 40)
Scheme 2: Mass spectral fragmentation pattern of
2-[{4-morpholino-1-sulphonyl) sydnon-3-yl}]-1,3,4- thiadiazino (6,5-b) indoles 4a

DUbEy et al., Orient. J. Chem., Vol. 30(1), 271-278 (2014)
277
CONCLUSION
albendazole standard. On the basis of SAR,
morphloine substitution seems to be very vital
Pharmacological evaluation data revealed for biological activity profile. Morpholino sydnonyl
that incorporation of secondary amines into substituted indole i.e.2-[{(4-morpholino-1-sulphonyl)
compound 3 i.e.2-[(4-Sulphoyl chloride)sydon-3-yl]- sydnon-3-yl}]-1,3,4-thiadiazino(6,5-b)indole 4a,
1,3,4-thiadiazino(6,5-b) indoles brought significant showed promising drug canditure among the all
efficacy in to biological activity. Compound 4a & 4e screened derivatives.
were the only compounds which displayed significant
antimicrobial activity against all the selected panel
of pathogens but order of efficacy was 4a > 4e.
During insecticidal activity against P. americana,
ACKNOwLEDGEMENTS
We are thankful for SAIF, Punjab University,
compound 4a showed remarkable potential in India for spectral, elemental analysis and Department
comparison to used standard cypermethrin. Again of Pathology, L.L.R.M. Medical College, India for
compound 4a was the only compound who showed biological activities.
better antihelmitic activity in compare to applied
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