International Journal of Chemical Research, ISSN: 0975-3699, Volume 2, Issue 2, 2010, pp-17-20
17
Copyright © 2010, Bioinfo Publications,
International Journal of Chemical Research, ISSN: 0975-3699, Volume 2, Issue 2, 2010
Synthesis of some new amides and their toxicological effect on an
insect Spodoptera litura
Saxena C.M.*
1
, Singh R.K.
1
, Sanjay Ashthana
2
, Archna Saxena
1
Research Laboratory; Department of Chemistry, D.B.S. P.G. College, Kanpur, India,
drcmsaxena01@gmail.com
Research Laboratory; Department of Chemistry, D.A.V. P.G. College, Kanpur, India
Abstract- Some novel organic amides were synthesized by the reaction of glycine/cystiene and
ethylene diamine with respective organic acids (succinic acid, maleic acid, tartaric acid and oxalic acid).
The newly synthesized compounds were isolated as crystalline solid and have sharp melting point. The
compounds were characterized by their elemental, I.R., NMR spectral analysis along with their activity
against an insect responsible for the damage of Indian crops Spodoptera litura. It was found that the
compounds show moderate efficacy against the insect.
Key Wards: Glycine, ethylenediamine, succinic acid, maleic acid, oxalic acid, tartaric acid, insecticidal
activity, Spodoptera litura.
Introduction
In recent year literature survey revealed that
nitrogen and sulfur containing compounds [1-3]
are potentially active against cancer, viral and
fungal disease [4, 5]. Amines in general have
been known to be biologically active [6] and the
effect of presence of various constituents in the
amines increases their antimicrobial and
insecticidal activity, has been investigated [7,
8]. The compounds having amino acid have
proven to be potentially active against various
bacterial and fungal strains and many of them
got wide acceptance in clinical trials [9, 10].
The differential inhibition of cytochrome P-450
between pathogenic bacterial and fungal
strains and human beings is the basis for the
clinically important amino acid as antimicrobial
agents. It may be found that the inhibition can
be determined by the differential
complementarities between the structures of
antimicrobial agent and the active sites of
enzymes responsible for microbial activity.
Insects are found in almost all types of
environment. They affect man's interest in a
number of ways; insects like mosquitoes and
housefly spread large number of diseases like
malaria, dengue and cholera in addition to
painful bites. Further, the compounds
containing amide moiety has also attracted
attention due to their important role as
insecticides and pesticides to save our Indian
crops [11]. In view of the, important behavior of
amines and amino acid, the present
communication deals with the synthesis,
characterization and insecticidal activity of
some new amide of amino acid.
Results and discussion
The amide was generally prepared by using
following method
The newly prepared compounds were
crystallized after vacuum distillation. The
compounds have sharp melting point. The
further characterization of these entire
compounds was done by elemental analysis,
I.R and NMR spectral data followed by
antimicrobial activity.
I.R. spectra
The infrared spectra of newly synthesized
amides of amino acids were recorded in
KBr/CsI pellets in the range of 4000-200cm
-1
.
The I.R. spectra of the entire compound clearly
exhibit absorption bands due to amides and
methylene groups. The absorption frequencies
due to carbonyl groups in amide have been
fully assigned.
1
H-NMR spectra
The
1
H-NMR spectra of the amide of amino
acids were recorded in CDCl 3 at room
temperature using TMS as standard. The
peaks values suggested the presence of
secondary amides group along with methylene
groups in the compound. The peak’s located at
δ8.0 ppm (for secondary amides) while the
peaks value appears at δ2.46, δ3.46 and δ4.09
in case of compound (A) suggested the
presence of six methylene group in the
compound. The peaks values for other
compounds are very close to the first
compound indicating the presence of
secondary amides and methylene proton.
Contact toxicity
The contact toxicity of the compounds is given
in Table-2. It was found that approximately all
these compounds are active against the insect
larvae of Spodoptera litura in different
concentrations. The compounds 3, 4 and 5
show higher toxicity against the larvae while
the rest of the compounds show moderate
toxicity. These compounds are generally used
as emulsion by adding tween 20 emulsifier in
the dissolved compounds. The emulsion of the
compounds then applies on the dorsal surface
of the insect which affect the nervous systems
of the insect larvae and ultimately causing
death of the insects.
Stomach toxicity
The stomach toxicity of the compounds was
given in Table-3. The toxicity of these