Synthesis and insect antifeedant activities of some substituted styryl 3,4-dichlorophenyl ketones

Article abstract of DOI:10.1016/j.saa.2009.10.003

Sixteen substituted styryl 3,4-dichlorophenyl ketones [(2E)-1-(3,4-dichlorophenyl)-3-phenyl-2-propen-1-ones] were synthesized using eco-friendly benign stereoselective crossed-aldol reaction. They are characterized by their analytical, infrared, NMR and m

Full text of DOI:10.1016/j.saa.2009.10.003

Spectrochimica Acta Part A 75 (2010) 152–156
Contents lists available at ScienceDirect
Spectrochimica Acta Part A: Molecular and
Biomolecular Spectroscopy
journal homepage: www.elsevier.com/locate/saa
Synthesis and insect antifeedant activities of some substituted styryl
3,4-dichlorophenyl ketones
G. Thirunarayanana,∗, S. Suryaa, S. Srinivasana, G. Vanangamudib, V. Sathiyendiranc
a Department of Chemistry, Annamalai University, Annamalainagar 608 002, Chidambaram, Tamilnadu, India
b PG & Research Department of Chemistry, Govt. Arts College, Chidambaram 608 102, India
c Department of Chemistry, Sourastra College, Madurai 625 004, India
a r t i c l e i n f o
a b s t r a c t
Article history:
Received 19 June 2009
Received in revised form 2 October 2009
Accepted 8 October 2009
Sixteen substituted styryl 3,4-dichlorophenyl ketones [(2E)-1-(3,4-dichlorophenyl)-3-phenyl-2-propen-
1-ones] were synthesized using eco-friendly benign stereoselective crossed-aldol reaction. They are
characterized by their analytical, infrared, NMR and mass spectral data. The insect antifeedant activities
of these chalcones were evaluated using Caster semilooper and Achoea janata L.
© 2009 Elsevier B.V. All rights reserved.
Keywords:
Styryl 3,4-dichlorophenyl ketones
Solvent free synthesis
IR and NMR spectra
Insect antifeedant activities
1. Introduction
[16] reported aqueous potassium hydroxide used as a reagent
for synthesis of some aryl chalcones by grinding aryl aldehydes
Green chemistry provides good eco-friendly methods for syn-
thesis of organic compounds without solvent. Among these
methods the aqueous phase reaction is very interesting due to
operative simplicity, easy work up, good yield, non-hazardous
conditions and being safer for the environment. Chemists and envi-
ronmental scientists have reported various solvent methods for
organic synthesis. The use of bases for synthesis of chalcones with
or without solvent is important [1]. A literature survey reveals that
there are few papers reporting synthesis of chalcones using bases
in aqueous phase aldol condensation reaction between ketones
and aldehydes. Various reagents are used for solvent free synthesis
like, metals and metal chelates [2], carbonates [3], chiral boronate
ester [4], phosphate [5], organolithium [6], sodium hydroxide [7],
silica-sulphuric acid [8], alumina [9], organic ionic liquids [10],
metal-nanoparticles [11] and potassium hydroxide-ethanol [12].
Kalluriya and Ray [13] synthesized sydenone chalcones with more
than 60% yield using grinding of aqueous sodium hydroxide-
heterogeneous reaction medium with aldehydes. Hassen and
co-workers [14] reported more than 60% yield of some heteroaryl
chalcones obtained by the solvent free reaction with aldehydes in
20 ◦C cooling condition in presence of surfactants. Venkat Reddy
et al. [15] reported more than 70% yield of chalcones synthesized
using zinc chloride and microwave techniques. Thirunarayanan
and ketones. The authors wish to report an efficient and selective
method for condensation of 3,4-dichlorophenyl methyl ketones
with various m- and p-substituted benzaldehydes under solvent
free conditions by stirring the reactants with sodium hydroxide
at room temperature to yield the respective E-2-propen-1-ones.
Studies of quantitative structure property relationship and insect
antifeedant activities are likewise reported. In this method during
stirring of 3,4-dichloro acetophenone and aldehydes, they decom-
posed slowly forming the products in good yield and the reaction
time is lower than in the solution phase thermal method. The
methylene units of chalcones derived from cyclic or acyclic ketones
are found in many naturally occurring compounds and they are
useful for the synthesis of pyrimidine derivatives [17]. The basic
skeleton of chalcones is widely represented in natural products
and are known to have multipronged activity [18]. Many of the
chalcones are used as agrochemicals and drugs [19].
2. Experimental
All chemicals used were purchased from Sigma–Aldrich and E-
Merck chemical company. Melting points of all chalcones were
determined in open glass capillaries on Mettler FP51 melt-
ing point apparatus and are uncorrected. Infrared spectra (KBr,
4000–400 cm−1) were recorded on AVATAR-300 Fourier transform
spectrophotometer. INSTRUM AV300 operating at 500 MHz for 1
H
∗
spectra and 125.46 MHz for 13C spectra in CDCl3 solvent using TMS
as internal standard. Electron impact (EI) (70 eV) and chemical ion-
Corresponding author. Tel.: +91 4144 220015.
E-mail address: drgtnarayanan@gamil.com (G. Thirunarayanan).
1386-1425/$ – see front matter © 2009 Elsevier B.V. All rights reserved.
doi:10.1016/j.saa.2009.10.003

G. Thirunarayanan et al. / Spectrochimica Acta Part A 75 (2010) 152–156
153
Scheme 1.
Table 1
Physical constants, microanalysis and mass spectral data of substituted styryl 3,4-dichlorophenyl ketones.
Entry
X
Molecular
formula
Molecular
weight
Time Yield M.p. (◦C)
Found (Calcd)
Mass m/z
(m)
(%)
C
H
N
–
1
H
C15H10Cl2O
276.14
45
91
100–101
64.82 (65.01)
3.59 (3.64)
276 (M+), 278, 280, 243, 241, 212, 198, 178,
174, 147, 146, 145, 131, 109, 107, 104, 103, 88,
78, 77, 75, 74, 73, 63, 52,
2
3
m-NH2
p-Br
C15H11Cl2NO 291.15
C15H9BrCl2O 355.91
40
50
86
89
111–112
168–169
61.62 (61.67)
50.55 (50.60)
3.94 (3.79)
2.35 (2.55)
4.72 (4.79)
291 (M+), 293, 295, 280, 241, 240, 226, 197,
178, 166, 147, 107, 95, 88, 75, 51
356 (M+), 357, 358, 360, 322, 321, 319, 165,
149, 277, 276, 275, 214, 212, 181, 147, 145,
137, 136, 124, 111, 103, 106, 102, 95, 75, 50
311 (M+), 313, 315, 276, 241, 149, 137, 136,
125, 111, 102, 95, 88, 51
4
5
o-Cl
C15H9Cl3O
C15H9Cl3O
311.86
311.86
45
50
88
85
121–122
145–146
57.78 (57.82)
57.71 (57.82)
2.85 (2.91)
2.84 (2.91)
–
–
m-Cl
311 (M+), 312, 313, 315, 276, 278, 277, 275,
247, 214, 208, 179, 175, 173, 149, 137, 105,
102, 75, 74, 68, 51.
6
p-Cl
C15H9Cl3O
311.86
50
90
142–143
57.79 (57.82)
2.88 (2.91)
–
311 (M+), 312, 313, 315, 309, 278, 277, 275,
249, 213, 212, 173, 166, 164, 146, 139, 138,
137, 111, 110, 108, 102, 101, 88, 75, 74, 63, 51.
321 (M+), 323, 325, 320, 308, 277, 250, 225,
174, 149, 136, 133, 120, 95, 88, 63, 50.
295 (M+), 297, 299, 276, 251, 241, 213, 178,
165, 149, 137, 136, 125, 111, 102, 95, 88, 51
293 (M+), 295, 297, 292, 276, 251, 241, 226,
178, 165, 149, 137, 136, 125, 111, 102, 95, 91,
88, 51.
7
8
9
p-N(CH3)2 C17H15Cl2NO 321.07
40
55
40
88
85
88
125–126
103–105
107–108
63.72 (63.76)
60.98 (61.04)
61.39 (61.46)
4.68 (4.72)
2.95 (3.07)
3.38 (3.44)
4.32 (4.37)
–
p-F
C15H9Cl2FO
C15H10Cl2O2
295.13
293.14
o-OH
10
11
12
13
p-OH
C15H10Cl2O2
C16H12Cl2O2
C16H12Cl2O2
C16H12Cl2O
293.14
306.12
306.12
290.27
35
45
40
35
91
90
90
91
117–118
105–106
152–153
137–138
61.41 (61.46)
62.49 (62.56)
62.54 (62.56)
65.93 (66.00)
3.40 (3.44)
3.88 (3.94)
3.90 (3.94)
4.09 (4.15)
293 (M+), 295, 297, 292, 276, 251, 241, 226,
178, 165, 149, 137, 136, 133, 125, 107, 111,
102, 95, 91, 88, 51.
m-OCH3
p-OCH3
p-CH3
306 (M+), 307, 308, 310, 291, 273, 271, 241,
237, 225, 206, 179, 162, 161, 149, 136, 133,
123, 109, 108, 103,90, 89, 78, 63, 51
306 (M+), 307, 308, 310, 291, 273, 271, 237,
225, 206, 179, 162, 149, 136, 133, 123, 109,
108, 89, 78, 63, 51
–
290 (M+), 292, 294, 282, 281, 277, 275, 257,
255, 226, 221, 208, 175, 147, 146, 145, 118,
115, 109, 95, 91, 76, 65, 51.
14
15
o-NO2
C15H9Cl2NO3 321.87
C15H9Cl2NO3 321.87
55
60
86
88
184–185
218–219
66.36 (66.42)
65.34 (66.42)
3.65 (3.72)
3.69 (3.72)
4.98 (5.16)
5.01 (5.16)
321 (M+), 323, 325, 283, 281, 252, 221, 176,
149, 146, 136, 135, 95, 72, 58.
m-NO2
321 (M+), 323, 325, 324, 305, 306, 304, 288,
287, 286, 283, 281, 274, 240, 224, 212,
209,208, 193, 190, 176, 174, 172, 149, 146,
136, 135, 130, 129, 110, 109, 89, 74, 63, 51.
321 (M+), 323, 325, 324, 305, 288, 287, 283,
281, 274, 240,224,212, 208, 193, 190, 176, 174,
149, 146, 136, 130, 129, 110, 74, 63, 51.
16
p-NO2
C15H9Cl2NO3 321.87
50
91
205–206
66.40 (66.42)
3.66 (3.72)
5.11 (5.16)

154
G. Thirunarayanan et al. / Spectrochimica Acta Part A 75 (2010) 152–156
Table 2
Infrared spectral data (␯, cm−1) of substituted styryl 3,4-dichlorophenyl ketones.
Entry
X
CO (s-cis)
CO (s-trans)
CHop vinyl
CHip vinyl
CH CHop vinyl
C
C
op vinyl
Subst. styryl part
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
H
1659.75
1665.21
1659.29
1662.04
1664.08
1659.46
1651.65
1662.14
1664.38
1666.38
1646.45
1656.48
1659.71
1668.28
1668.18
1687.67
1601.25
1628.39
1600.62
1603.99
1606.23
1599.93
1549.35
1601.03
1613.28
1609.25
1603.76
1593.73
1598.91
1607.55
1607.38
1589.52
761.30
753.26
737.31
735.65
773.39
732.69
732.69
738.65
748.34
753.48
724.74
717.72
733.50
741.98
742.00
772.87
1129.93
1134.23
1127.11
1136.87
1134.17
1128.29
1128.29
1127.46
1134.23
1142.46
1144.24
1134.54
1123.36
1150.52
1150.28
1151.01
1026.31
1022.45
1048.80
1040.67
1049.16
1049.16
1049.16
1044.70
1066.37
1064.37
1073.69
1033.62
1049.81
1046.16
1046.07
1027.28
521.50
527.43
567.48
534.23
563.74
567.71
567.71
555.84
546.26
536.24
545.87
515.72
524.51
583.71
583.66
561.58
—
m-NH2
p-Br
o-Cl
m-Cl
p-Cl
3346.58 (–NH2)
—
—
—
—
—
—
3435.86 (–OH)
3343.86 (–OH)
1236.17 (C–O–C)
1236.17 (C–O–C)
2857.81 (CH3)
1521.03 (–NO2)
1515.26 (–NO2)
1515.26 (–NO2)
p-F
p-N(CH3)2
o-OH
p-OH
m-OCH3
p-OCH3
p-CH3
o-NO2
m-NO2
p-NO2
ization mode FAB+ mass spectra were recorded with a VARIAN
500 spectrometer. Microanalysis of all chalcones was performed
in Elementar Model Vario EL III Analyzer.
1-(3,4-dichlorophenyl)-3-phenyl-2-propen-1-ones in an excellent
yield with high stereoselectivity. Efficient stirring of an equimolar
quantity of 3,4-dichloroacetophenone and various substituted aryl
aldehydes in aqueous sodium hydroxide solution in presence of
cetyltrimethylammonium bromide (CTABr) as surfactant at room
temperature, feasible stereoselective crossed-aldol condensation
with precipitation of the 3-phenyl-1-3,4-dichlorophenylprop-2-
ene-1-ones in high yields with in the short time (t) as shown in
Table 1. This methodology offers significant advantages over con-
ventional methods such as, (i) safe, clean and simple methodology,
(ii) modified stereoselectivity reaction, (iii) improved reaction rates
and increased yields through suppression of side reactions. (iv)
aqueous alkali metal hydroxides replace alkoxides. (v) reaction was
carried out at room temperature and easier- workup and (vi) avoid
the expensive and hazard organic solvents.
2.1. General procedure for synthesis of substituted styryl
3,4-dichlorophenyl ketones
Appropriate mixture of 3,4-dichloroacetophenone (100 mmol)
and m- and p-substituted benzaldehydes (100 mmol) and cetyl
trimethyl ammonium bromide (CTABr) (15 mmol) were added
to an aqueous solution of sodium hydroxide (200 ml 0.5 M). The
reaction mixture was vigorously stirred at room temperature
(Scheme 1) for the time reported in Table 1. Completion of reac-
tion was confirmed by TLC. The product was filtered and washed
with cold water and recrystallized from ethanol, dried well and
kept in a desiccator. The analytical and Mass spectral data of all
chalcones are presented in Table 1 and the spectral data are shown
in Tables 2–4.
3.1. Insect antifeedant activity
The multipronged activities present in different chalcones are
intended to examine their insect antifeedant activities against
caster semilooper. The larvae’s of Achoea Janata L. were reared as
described on the leaves of caster Riclmus Cammunls in the labora-
tory at the temperature range of 26 1 ◦C and a relative humidity
of 75–85%. The leaf–disc bioassay method [16] was used against the
4th instar larvae to measure the antifeedant activity. The 4th instar
larvae were selected for testing because the larvae at this stage feed
very voraciously.
3. Results and discussion
Our previous investigations [20–25] deal with to carbon–carbon
bond formation and we studied in this article the crossed-aldol con-
densation of 3,4-dichloroacetophenone and a variety of different
substituted aryl aldehydes. This occurs in water at room temper-
ature and in the presence of cetyltrimethylammonium bromide
(CTABr) as the proper cationic surfactant for the synthesis of (2E)-
Table 3
1H NMR spectral data (␦, ppm) of substituted styryl 3,4-dichlorophenyl ketones.
ꢀ
Entry
X
3,4-Dichloro phenyl ring
H6 (d, 1H)
vinyl H␣ (d, 1H)
vinyl H␤ (d, 1H)
Styryl Ph ring (m, 4H) Substituent in styryl part
ꢀ
ꢀ
H2 (s, 1H) H5 (d, 1H)
1
2
3
4
5
6
7
8
H
7.978
7.794
7.893
8.075
8.095
8.079
7.421 (J = 2.12 Hz) 7.628 (J = 2.12 Hz) 7.536 (J = 15.2 Hz)
7.795 (J = 15.2 Hz)
7.732 (J = 16.3 Hz)
7.762 (J = 15.6 Hz)
8.233 (J = 18.5 Hz)
7.751 (J = 17.0 Hz)
7.771 (J = 15.5 Hz)
7.813 (J = 17.7 Hz)
7.872 (J = 16.3 Hz)
8.215 (J = 18.4 Hz)
7.788 (J = 17.8 Hz)
7.715 (J = 17.8 Hz)
7.808 (J = 16.0 Hz)
7.804 (J = 15.5 Hz)
7.915 (J = 15.5 Hz)
8.169 (J = 16.0 Hz)
7.298-7.372
6.561-6.973
7.012–7.421
7.255–7.302
7.350–7.420
7.562–7.855
6.651–7.321
6.813–7.113
6.671–7.238
6.652–7.182
6.710–7.154
7.564–7.619
7.217–7.257
7.622–7.702
7.575–8.123
–
m-NH2
p-Br
o-Cl
m-Cl
p-Cl
p-N(CH3)2 7.913
p-F
o-OH
p-OH
m-OCH3
p-OCH3
p-CH3
o-NO2
m-NO2
p-NO2
7.381 (J = 3.3 Hz)
7.284 (J = 3.2 Hz)
7.432 (J = 2.5 Hz)
7.509 (J = 1.5 Hz)
7.391 (J = 2.3 Hz)
7.726 (J = 4.6 Hz)
7.558 (J = 3.2 Hz)
7.441 (J = 5.3 Hz)
7.514 (J = 4.7 Hz)
7.174 (J = 4.7 Hz)
7.828 (J = 2.5 Hz)
7.527 (J = 2.0 Hz)
8.284 (J = 1.8 Hz)
7.423 (J = 4.2 Hz)
7.543 (J = 3.0 Hz)
7.573 (J = 3.3 Hz)
7.601 (J = 3.2 Hz)
7.691 (J = 2.5 Hz)
7.598 (J = 1.5 Hz)
7.828 (J = 2.3 Hz)
7.835 (J = 4.6 Hz)
7.601 (J = 3.2 Hz)
7.653 (J = 5.3 Hz)
7.765 (J = 4.7 Hz)
7.563 (J = 4.7 Hz)
7.845 (J = 2.5 Hz)
7.551 (J = 2.0 Hz)
7.763 (J = 1.8 Hz)
7.878 (J = 4.2 Hz)
7.769 (J = 3.0 Hz)
7.356 (J = 16.3 Hz)
7.526 (J = 15.6 Hz)
7.323 (J = 18.5 Hz)
7.435 (J = 17.0 Hz)
7.410 (J = 15.5 Hz)
7.491 (J = 17.7 Hz)
7.532 (J = 16.3 Hz)
7.362 (J = 18.4 Hz)
7.714 (J = 17.8 Hz)
7.321 (J = 17.8 Hz)
7.319 (J = 16.0 Hz)
7.389 (J = 15.5 Hz)
7.756 (J = 15.5 Hz)
7.263 (J = 16.0 Hz)
3.721 (s, 2H, –NH2)
–
–
–
–
2.647 (s, 6H, N(CH3)2)
–
–
–
3.934 (s, 3H, –OCH3)
3.934 (s, 3H, –OCH3)
2.392 (s, 3H, (CH3))
–
–
–
8.032
7.812
7.981
7.813
8.086
8.071
8.531
8.185
7.843
9
10
11
12
13
14
15
16
7.561 (J = 16.25 Hz) 7.807 (J = 16.25 Hz) 7.265–7.563

G. Thirunarayanan et al. / Spectrochimica Acta Part A 75 (2010) 152–156
155
Table 4
13C NMR spectral data (ı, ppm) of substituted styryl 3,4-dichlorophenyl ketones.
Entry
X
CO
C␣
C␤
C1
C2
C3
C4
C5
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
H
187.87
180.10
181.30
187.85
187.53
187.63
181.33
190.23
188.79
188.32
188.80
187.96
187.99
188.87
187.89
190.87
120.83
121.40
122.28
123.55
122.02
121.23
122.82
122.65
121.33
121.48
122.14
118.53
119.85
122.48
122.25
122.34
146.03
144.91
144.40
141.73
144.24
144.19
147.32
145.83
146.52
146.27
145.52
145.93
146.16
142.83
141.84
144.52
136.28
137.32
133.56
133.34
136.29
133.36
123.17
130.73
116.78
127.67
135.24
127.44
131.76
130.17
136.45
142.25
127.16
111.08
128.21
131.59
126.97
127.48
127.57
127.33
159.83
127.08
111.29
127.23
128.76
149.71
124.03
127.34
128.64
149.30
132.71
128.82
135.09
129.35
115.28
116.72
115.23
114.58
163.14
114.46
129.80
120.71
148.66
120.74
128.43
114.72
122.48
129.66
128.03
133.38
148.91
163.54
130.40
158.87
114.61
162.05
137.93
127.87
122.23
150.05
128.64
130.20
132.71
127.11
130.30
129.35
115.28
116.72
120.14
114.58
130.38
114.46
129.80
134.46
130.05
120.74
m-NH2
p-Br
o-Cl
m-Cl
p-Cl
p-N(CH3)2
p-F
o-OH
p-OH
m-OCH3
p-OCH3
p-CH3
o-NO2
m-NO2
p-NO2
ꢀ
ꢀ
ꢀ
ꢀ
ꢀ
ꢀ
Entry
X
C6
C1
C2
C3
C4
C5
C6
Substituent in styryl part
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
H
127.16
117.25
128.21
127.84
124.56
127.48
127.57
127.33
127.78
127.08
119.87
127.43
128.76
127.56
131.92
127.34
137.30
137.90
138.92
137.45
137.43
137.49
136.93
136.27
137.67
136.94
137.57
137.02
137.16
136.92
138.21
137.75
130.99
130.50
132.71
132.38
130.79
130.49
131.54
131.07
130.01
130.92
131.36
130.68
131.76
131.95
131.92
132.36
133.28
130.91
133.92
133.57
133.41
132.95
133.01
133.27
133.36
133.38
133.72
133.20
133.24
133.60
133.83
133.28
137.74
140.92
139.92
139.28
137.69
137.56
138.92
140.11
140.92
140.29
139.35
138.11
141.66
139.54
140.32
138.97
130.99
129.36
129.02
128.21
129.66
130.77
129.75
130.31
130.32
130.01
130.11
129.28
130.38
130.42
128.15
130.11
130.33
–
–
–
–
–
–
m-NH2
p-Br
o-Cl
m-Cl
p-Cl
p-N(CH3)2
p-F
o-OH
p-OH
m-OCH3
p-OCH3
p-CH3
o-NO2
m-NO2
p-NO2
121.89
132.71
130.78
130.83
130.84
130.82
131.32
130.81
132.74
130.25
130.64
130.48
130.95
130.92
130.74
46.63 (N(CH3)2)
–
–
56.39 (OCH3)
55.45 (OCH3)
21.59 (CH3)
–
–
–
3.2. Measurement of insect antifeedant activity of chalcones
The results of the antifeedant activity of substituted styryl
3,4,-dichlorophenyl ketones presented in Table 5 reveal that the
compounds 3–6 are found to reflect remarkable antifeedant among
all other chalcones. This test is performed with the insects’ which
ate only two-leaf disc soaked under the solution of this compound.
Compounds 4 and 5 also show enough antifeedant activity but
lesser than 6. Further compound 6 was subjected to measure the
antifeedant activity at different 50, 100, 150 ppm concentrations
and the observation reveals that as the concentrations decreased,
the activity also decreased. It is observed from the results in Table 6
that the ketone 6 (2E)-1-(3,4-dichlorophenyl)-3-(4-chlorophenyl)-2-
propen-1-one shows an appreciable antifeedant activity at 200 ppm
concentration.
Leaf discs of a diameter of 1.85 cm were punched from caster
leaves with the petioles intact. All ketones were dissolved in ace-
tone at a concentration of 200 ppm dipped for 5 min. The leaf discs
were air-dried and placed in 1 l beaker containing little water in
order to facilitate translocation of water. Therefore the leaf discs
remain fresh throughout the duration of the rest, 4th instar lar-
vae of the test insect, which had been preserved on the leaf discs
of all chalcones and allowed to feed on them for 24 h. The area of
the leaf disc consumes were measured by Dethler’s [26] method.
The observed antifeedant activity of chalcones was presented in
Table 5.
Table 5
Antifeedant activity of substituted styryl 3,4-dichlorophenyl ketones. Number of leaf discs consumed by the insect (Values are mean + SE of five).
Entry
X
4–6
pm
6–8
pm
8–10
pm
10–12
pm
12–6
am
6–8
am
8 am–12 Noon
12 Noon–2 pm
2–4
pm
Total leaf disc consumed in 24 h
1
2.
3
4
5
6
7
8
H
1
1
1
1
0.5
1
0.5
0.5
0.5
0.5
1
0
1
1
0.5
1
0.5
0.5
0.5
0
1
1
1
1
0.25
0.25
0
1
1
1
1
1
0.25
0
0
1
1
1
1
0.5
0.25
0
0
1
1
8
8
m-NH2
p-Br
o-Cl
m-Cl
p-Cl
0.5
0.5
0.25
0.5
0.25
0
0.5
0.5
0
0.25
1
0.25
0.25
0.25
0.5
2
0.25
0.25
0.25
0.25
2
1.5
2.5
1.5
0.5
9
p-N(CH3)2
p-F
0
0
1
2
2
0
9
9
o-OH
p-OH
m-OCH3
p-OCH3
p-CH3
o-NO2
m-NO2
p-NO2
1
1
0.5
1
0.5
2
1
2
2
0.5
0.5
3
3
2
.05
2
0.25
0.5
0.5
3
0.5
1
1
1
2
1
1
2
1
0
0.5
1
2
1
1
1
0.5
0
0.5
0
1
1
1
1
0.25
1
1
0.5
0.5
0.5
1
1
0
1
1
1
1
1
1
1
0
1
1
0
0
0
7.5
9
5
9
9
12
12
10
10
11
12
13
14
15
16
2
1
3
2
1
0.5

156
G. Thirunarayanan et al. / Spectrochimica Acta Part A 75 (2010) 152–156
Table 6
Antifeedant activity of compound 6 (2E)-1-(3,4-dichlorophenyl)-3-(4-chlorophenyl)-2-propen-1-one at 4 different concentrations -number of leaf discs consumed by the insect
(Values are mean + SE of five).
ppm
4–6
pm
6–8
pm
8–10
pm
10–12
pm
12–6
am
6–8
am
8 am–12 Noon
12 Noon–2 pm
2–4
pm
Total leaf disc consumed in 24 h
50
100
150
0.5
0
0
0.5
0.25
0
0
0.25
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0.1
0.05
0
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