Synthesis and Insecticidal Efficacy of Novel Bis Quinazolinone Derivatives

Article abstract of DOI:10.1002/jhet.2445

A novel bis benzoxazin-4-one derivative has been synthesized and utilized to construct a new series of bis quinazolin-4(3H)-one derivatives via the reactions with different nitrogen nucleophiles namely, primary amines (ammonia, ethanolamine, and 4-aminoantipyrine), secondary amines (morpholine and piperidine), diamine (o-phenylenediamine), hydrazine hydrate, and hydroxylamine. The insecticidal efficacy of newly synthesized compounds was also studied. The structural features of the synthesized compounds were assigned by spectral analysis.

Full text of DOI:10.1002/jhet.2445

Month 2015
Synthesis and Insecticidal Efficacy of Novel Bis Quinazolinone Derivatives
a
a
b
c
*
Manal M. Elshahawi, Ahmed K. EL-Ziaty, Jehan M. Morsy, and Aly F. Aly
aChemistry Department, Faculty of Science, Ain Shams University, Abbasia, Cairo 11566, Egypt
bLaboratory of Synthetic Organic Chemistry, Chemistry Department, Faculty of Education, Ain Shams University, Roxy,
Cairo 11711, Egypt
cPesticides Formulation Laboratory, Central Agricultural Pesticides Laboratory Agricultural Research Center, El Dokki,
Giza 12622, Egypt
*
E-mail: morsy_Jehan@yahoo.com
Received December 13, 2014
DOI 10.1002/jhet.2445
Published online 00 Month 2015 in Wiley Online Library (wileyonlinelibrary.com).
A novel bis benzoxazin-4-one derivative has been synthesized and utilized to construct a new series of bis
quinazolin-4(3H)-one derivatives via the reactions with different nitrogen nucleophiles namely, primary
amines (ammonia, ethanolamine, and 4-aminoantipyrine), secondary amines (morpholine and piperidine),
diamine (o-phenylenediamine), hydrazine hydrate, and hydroxylamine. The insecticidal efficacy of newly
synthesized compounds was also studied. The structural features of the synthesized compounds were
assigned by spectral analysis.
J. Heterocyclic Chem., 00, 00 (2015).
INTRODUCTION
economically important cultivated crops such as cotton,
soybean, groundnut, tobacco, and vegetables [17]. It has
been found that it causes 26–100% yield loss in the field
[18]. The present study aimed to evaluate the newly syn-
thesized bis quinazolin-4(3H)-one derivatives against cot-
ton leaf worm. The bis-benzoxazin-4-one derivative 2 as
a key starting material has been obtained in good yield
by cyclization of 2({4-[(2-carboxyphenyl) amino]-4-
oxobutanoyl} amino) benzoic acid 1, which was obtained
via the reaction of anthranilic acid and succinyl chloride in
pyridine (Scheme 1). The structure of compound 2 was de-
duced from correct analytical and spectroscopic data. IR
spectrum displays an absorption band for carbonyl group at
Benzoxazinones (BAs) are natural products and represent
part of the Gramineae defense system against insects, bacteria,
and fungi [1–3]. Quinazolines exhibit a broad spectrum of
biological activity including anti-inflammatory and antiplate-
let aggregation [4], cytotoxicity [5], and cardiovascular activ-
ity [5,6]. These compounds also act as antihistaminic [7,8],
antifungal, and antimalarial agents [9,10], and they exhibit
potential psychomotor activity [11]. Pronounced pharmaco-
logical and biological activities of both benzoxazinones and
quinazolines stimulated us to continue our previous work
[12–16], for synthesis of novel heterocycles.
1
1756cmꢀ1, and the H-NMR (DMSO-d6) revealed signals
RESULTS AND DISCUSSION
at δ (ppm) at: 7.90–7.30 (m, 8H, ArH), 1.90 (s, 4H,
CH2CH2). Furthermore, the IE-MS of compound 2 shows
the correct molecular ion peak at m/z=320 (5%). (cf. the
The cotton leaf worm Spodoptera littoralis (Boisd) is a
serious pest causing enormous losses to many
© 2015 HeteroCorporation

M. M. Elshahawi, A. K. EL-Ziaty, J. M. Morsy, and A. F. Aly
Vol 000
Scheme 1
Experimental Section and Fig. 1). Aiming to synthesize
novel quinazolinone derivatives which expected to have sig-
nificant insecticidal efficiency, the benzoxazinone derivative
2 was subjected to react with different nitrogen nucleophiles.
The new quinazolinones were obtained via ring opening of
the benzoxazinone followed by ring closure under the influ-
ence of the reaction conditions.
Aminolysis of bis-benzoxazinone 2 with secondary
amines namely, morpholine and piperidine, in refluxing
dioxane provided bis-succinamide derivatives 3 and 4,
Figure 1. EI-MS fragmentation of compound 2.
Scheme 2
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

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Bis Quinazolinones as Efficient Insecticides
2({4-[(2-Carboxyphenyl)amino]-4-oxobutanoyl}amino)benzoic
acid 1. A solution of succinyl chloride (1.55g, 0.01mol) in
respectively. Upon treatment of bis-benzoxazinone 2
with hydroxylamine hydrochloride in boiling pyridine,
the quinazolinone derivative 5 was produced (Scheme 2).
Furthermore, fusion of 2 with ammonium acetate in
sand bath at 230°C gave the quinazolinone derivative 6.
Hydrazinolysis of 2 by stirring with hydrazine hydrate
(80%) in dioxane at room temperature for 1 h afforded
the quinazolinone derivative 7. The structural features of
quinazolinone 7 were chemically substantiated beside the
correct microanalytical and spectroscopic data from its
acetylating with freshly distilled acetic anhydride to give
the corresponding acetylating product 8. Moreover, 1,
dry ether (10mL) was added dropwise to a solution of
anthranilic acid (2.74g, 0.02mol) in pyridine (20mL) with
stirring. The reaction mixture was stirred for further 30min
at room temperature then poured into ice-cold water and
acidified with concentrated hydrochloric acid (35%). The
obtained precipitate was collected by filtration and washed
several times with water, dried, and crystallized from
benzene to give 1 as buff crystals, m.p: 234–236°C, Yield:
80%, IR (KBr, ν): 3332cmꢀ1 (NH, OH) and 1672cmꢀ1
1
(C¼O). H-NMR (DMSO) δ: 11.39 (br. s, 2H, 2COOH,
exchangeable with D2O), 8.12–7.34 (m, 8H, ArH), 4.98
(br. s, 2H, 2NH, exchangeable), 2.10 (s, 4H, CH2CH2). MS
[m/z, (%)]: 356 (missed), 276 (4)[M-(2H2O, CO2)], 247
(3.8), 146 (30), 129 (5.5), 119 (100), and 90 (53). Anal.
Calcd. for C18H16N2O6 (356): C, 60.67; H, 4.49; N, 7.87.
2-dibenzimidazol [1, 2-c] quinazolinoethan
9 was
obtained via reaction of bis-benzoxazinone 2 with
o-phenylenediamine in boiling dioxane (Scheme 2). How-
ever, bis-benzoxazinone 2 reacted with 4-aminoantipyrine
in refluxing dioxane to give the amide derivative 10. It is
known that reaction of primary aromatic amines with
benzoxazinones gives the corresponding quinazolinones
via oxazinone ring cleavage by the nucleophilic attack of
amino group on the carbonyl functionality followed by
ring closure through attack of nitrogen-lactam form
―CONH― on the double bond of the lactim form
―N¼C―OH with the elimination of water molecule. In
case of 4-aminoantipyrine, the cyclization process seems
difficult because of the bulk of antipyrine moiety, and
hence, the amide 10 was formed instead of the correspond-
ing quinazolinone. On the other hand, treatment of 2 with
ethanolamine in refluxing dioxane afforded quinazolinone
derivative 11 (Scheme 2).
Found: C, 60.64; H, 4.30; N, 7.90.
2-{2-(4-Oxo-4H-benzo[d][1,3]oxazin-2-yl)ethyl}-4H-benzo[d]
[1,3]oxazin-4-one 2. A mixture of 1 (3.56g, 0.01mol) and
freshly distilled acetic anhydride (10 mL) was heated for
4 h on water bath. The reaction mixture was allowed to
cool, and the obtained solid was separated by filtration,
washed with petroleum ether 40–60°C, dried, and
crystallized from toluene to give 2 as green crystals, m.
p: 224–226°C, Yield: 85%, IR (KBr, ν): 1756 cmꢀ1
(C¼O) and 1641 cmꢀ1 (C¼N). 1H-NMR (DMSO) δ:
7.90–7.30 (m, 8H, ArH), 1.90 (s, 4H, CH2CH2). MS
[m/z, (%)]: 320 (5), 276 (9), 248 (8), 247 (15), 116 (4),
131 (2), and 90 (100). Anal. Calcd. for C18H12N2O4
(320): C, 67.50; H, 3.75; N, 8.75. Found: C, 67.64; H,
3.55; N, 8.90.
N1,N4-bis[2-(morpholine-4-carbonyl)phenyl]succinamide
3. A mixture of benzoxazinone 2 (1.0 g, 0.003 mol) and
CONCLUSION
The quinazolinone derivatives under investigation might
be used in a proper formulation form to invent new potent
pesticides to control cotton leaf worm S. littoralis in order
to decrease the loss in the global cotton yield.
morpholine (0.54 g, 0.006 mol) in dioxane (20 mL) was
heated under reflux for 3 h. The solid formed after
cooling was filtered off, dried, and then crystallized
from dioxane to give 3 as white crystals, m.p:
159–160°C, Yield: 70%, IR (KBr, ν): 3226, 3182 cmꢀ1
(NH) and 1682 cmꢀ1 (C¼O). 1H-NMR (DMSO) δ: 9.67
(br. s, 2H, 2NH, exchangeable with D2O), 7.46–7.23
(m, 8H, ArH), 3.43–3.38 (t, 8H, 2 CH2OCH2), 2.46
(t, 8H, 2 CH2NCH2), 2.04 (s, 4H, CH2CH2). MS [m/z, (%)]:
494 (2), 408 (6), 321 (80), 247 (14), 202 (85), 55 (100).
Anal. Calcd. for C26H30N4O6 (494): C, 63.16; H, 6.07; N,
11.33. Found: C, 63.24; H, 6.15; N, 11.40.
EXPERIMENTAL
Chemistry. All melting points were measured on Griffin
and Geory melting point apparatus and are uncorrected.
IR spectra were recorded on Pye Unicam SP 1200
1
spectrophotometer using KBr Wafer technique. H-NMR
spectra were determined on a Varian Gemini 200MHz
using TMS as internal standard (chemical shifts in δ-scale).
EI-MS were measured on a Schimadzu-GC-MS, QP 1000
EX instrument operating at 70eV. Elemental analyses were
carried out at the microanalytical unit, Faculty of Science,
Ain Shams University by using Perkin-Elmer 2400 CHN
elemental analyzer, and satisfactory analytical data ( 0.4)
were obtained for all compounds. The homogeneity of
the synthesized compounds was controlled by TLC
[Using TLC aluminum sheets silica gel F254 (Merck)].
N1,N4-bis[2-(piperidine-4-carbonyl)phenyl]succinamide 4.
A
mixture of benzoxazinone 2 (1.0g, 0.003mol) and piperidine
(0.54g, 0.006mol) in dioxane (20mL) was heated under
reflux for 4h. The solid formed after cooling was filtered
off, dried, and then crystallized from dioxane to give 4 as
white crystals, m.p: 160–162°C, Yield: 70%, IR (KBr, ν):
3200cmꢀ1 (NH) and 1691cmꢀ1 (C¼O). 1H-NMR
(DMSO) δ: 8.91 (br. s, 2H, 2NH, exchangeable with D2O),
7.64–7.31 (m, 8H, ArH), 3.43–3.38 (m, 12H,
2
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M. M. Elshahawi, A. K. EL-Ziaty, J. M. Morsy, and A. F. Aly
Vol 000
CH2CH2CH2), 2.82 (t, 8H, 2 CH2NCH2),1.94 (s, 4H, CH2CH2).
MS [m/z, (%)]: 490 (2), 406 (3), 321 (17), 247 (3), 202 (26),
162 (5), 84 (100). Anal. Calcd. for C28H34N4O4 (490): C,
68.57; H, 6.94; N, 11.43. Found: C, 68.49; H, 6.95; N, 11.40.
3-Hydroxy-2-[2-(3-hydroxy-4-oxo-3,4-dihydroquinazolin-2-yl)
ethyl]quinazolin-4-(3H)-one 5. A mixture of benzoxazinone 2
(1.0g, 0.003mol) and hydroxyl amine hydro chloride
(0.43g, 0.006mol) in pyridine (20mL) was heated under
reflux for 8h. The reaction mixture was concentrated and
the solid formed after cooling was washed with water,
filtered off, dried, and then crystallized from benzene to
give 5 as yellow crystals, m.p: 260–262°C, Yield: 75%, IR
(KBr, ν): 3115cmꢀ1 (OH) and 1649cmꢀ1 (C¼O). 1H-NMR
(DMSO) δ: 8.12–7.19 (m, 8H, ArH), 2.12 (s, 2H, 2OH),
1.91 (s, 4H, CH2CH2). MS [m/z, (%)]: 350 (24), 333 (100),
317 (27), 160 (18), 145 (25). Anal. Calcd. for C18H14N4O4
(350): C, 61.71; H, 4.03; N, 15.99. Found: C, 61.68;
4 h. The solid formed after evaporate the solvent was
filtered off, washed with petroleum ether 40–60, dried,
and then crystallized from ethanol to give 8 as blue
crystals, m.p: 236–238°C, Yield: 80%, IR (KBr, ν, cmꢀ1):
1737, 1702 cmꢀ1 (C¼O), 1606 (C¼N). MS [m/z, (%)]:
516 (30), 416 (25), 374 (78), 332 (23), 274 (11), 186 (63),
56 (100). H-NMR (DMSO) δ: 8.11–7.46 (m, 8H, ArH),
2.49 (s, 6H, 2CH3CO), 2.04 (s, 4H, CH2CH2). Anal.
Calcd. for C26H24N6O6 (516): C, 60.46; H, 4.65;
1
N, 16.27. Found: C, 60.50; H, 4.59; N, 16.30.
1, 2-Dibenzimidazol[1,2-c]quinazolinoethane 9. A mixture
of benzoxazinone 2 (1.0g, 0.003mol) and o-phenylenediamine
(0.675 g, 0.006 mol) in dioxane (20 mL) was heated under
reflux for 8h. The solvent was removed under reduced
pressure, and the solid formed was filtered off, dried,
and then crystallized from dioxane to give 9 as white
crystals, m.p: over 340°C, Yield: 80%, IR (KBr, ν):
3086 cmꢀ1 (CH―Ar), 1618cmꢀ1 (C¼N). MS [m/z, (%)]:
464 (8), 229 (33), 172 (20), 77 (20), 68 (33), 64 (45), 56
(100). 1H-NMR (DMSO) δ: 7.42–7.07 (m, 16H, ArH),
2.05 (s, 4H, CH2CH2). Anal. Calcd. for C30H20N6 (464):
C, 77.59; H, 4.31; N, 18,10. Found: C, 77.49; H, 4.49;
H, 3.99; N, 15.89.
2-[2-(4-Oxo-3,4-dihydroquinazolin-2-yl)ethyl]quinazolin-4-
(3H)-one 6. A mixture of benzoxazinone 2 (1.0 g,
0.003 mol) and ammonium acetate (1.5 g) was fused on
sand bath at 230°C for 2 h. The reaction mixture was
stirred with hot water for 15 min, and the solid formed
was filtered off, dried, and then crystallized from ethanol
to give 6 as pale yellow crystals, m.p: 290–292°C, Yield:
75%, IR (KBr, ν): 3175 cmꢀ1 (NH) ,1675 cmꢀ1 (C¼O),
N, 17.98.
N1,N4-bis[2-(4-aminoantipyrine-4-carbonyl)phenyl]succinamide
10. A mixture of benzoxazinone 2 (1.0 g, 0.003 mol) and
1
1610 (C¼N). H-NMR (DMSO) δ: 11.77 (s, 2H, 2NH,
4-aminoantipyrine (1.22g, 0.006mol) in dioxane (20 mL)
was heated under reflux for 8 h. The solvent was removed
under reduced pressure, and the solid formed was filtered
off, dried, and then crystallized from dioxane to give 10
as yellow crystals, m.p: 240–242°C, Yield: 78%, IR (KBr,
ν): 3253 cmꢀ1 (NH), 1670cmꢀ1 (C¼O). 1H-NMR
(DMSO) δ: 9.22 (s, 2H. NH exchangeable with D2O),
8.95 (s, 2H. NH exchangeable with D2O), 8.23–8.04 (m,
8H, ArH), 7.92–7.34 (m, 10H, ArH), 2.2 (s, 12H, 4CH3)
1.95 (s, 4H, CH2CH2). MS [m/z, (%)]: 728[M+2](35), 295
(35), 109 (36), 71 (26), 64 (100). Anal. Calcd. for
C40H38N8O6 (726): C, 66.11; H, 5.23; N, 15.43. Found:
exchangeable with D2O), 8.43–7.11 (m, 8H, ArH), 1.92
(s, 4H, CH2CH2). Anal. Calcd. for C18H14N4O2 (318):
C, 67.92; H, 4.40; N, 17.61. Found: C, 67.88; H, 4.33;
N, 17.65.
13C NMR for compound 6
MS [m/z, (%)]: 318 (5), 173 (4), 145 (4), 103 (8), 91 (7), 57 (100).
3-Amino-2-[2-(3-amino-4-oxo-3,4-dihydroquinazolin-2-yl)ethyl]
quinazolin-4-(3H)-one 7. A mixture of benzoxazinone 2
C, 65.88; H, 5.51; N, 15.42.
3-(2-Hydroxyethyl)-2-{2-[3-(2-hydroxyethyl)-4-oxo-3,4-
dihydroquinazolin-2-yl]ethyl}qunazolin-4(4H)-one 11. A mixture
(1.0 g, 0.003 mol) and hydrazine hydrate (0.31 g, 0.006) in
dioxane (20 mL) was stirred for 1 h. The solid formed was
filtered off, dried, and then crystallized from dioxane to
give 7 as white crystals, m.p: over 300°C, Yield: 90%, IR
(KBr, ν): 3316, 3204cmꢀ1 (NH2), 1672cmꢀ1 (C¼O),
1628 (C¼N). MS [m/z, (%)]: 348 (45), 332 (56), 317
(16), 158 (10), 144 (24), 173 (14), 198 (15), 186 (100).
1H-NMR (DMSO) δ: 8.23–7.34 (m, 8H, ArH), 2.12
(s, 4H, CH2CH2), (2H, NH2, hided under DMSO protons
signals). Anal. Calcd. for C18H16N6O2 (348): C, 62.07; H,
4.59; N, 24.14. Found: C, 62.16; H, 4.53; N, 24.22.
3-Diacetylamino-2-[2-(3-diacetylamino-4-oxo-3,4-dihydro
quinazolin-2-yl)ethyl] quinazolin-4-(3H)-one 8. A mixture of
quinazoline 7 (1.05 g, 0.003 mol) and freshly distilled
acetic anhydride (10 mL) was heated under reflux for
of benzoxazinone 2 (1.0 g, 0.003 mol) and ethanol amine
(0.49 g, 0.006 mol) in dioxane (20 mL) was heated
under reflux for 5 h. The solvent was removed under
reduced pressure, and the solid formed was filtered
off, dried, and then crystallized from ethanol to give
11 as white crystals, m.p: 178–180°C, Yield: 78%, IR
1
(KBr, ν): 3503 cmꢀ1 (OH), 1674 cmꢀ1 (C¼O). H-NMR
(DMSO) δ: 8.12–7.72 (m, 8H ArH), 4.12–3.82 (m, 8H,
2NCH2―CH2O) 3.64 (s, 2H, OH), 1.89 (s, 4H CH2―CH2)
MS [m/z, (%)]: 406 (9), 363 (47), 244 (17), 201 (35), 173
(44), 120 (100). Anal. Calcd. for C22H22N4O4 (406): C,
65.01; H, 5.42; N, 13.79. Found: C, 64.99; H, 5.32; N,
13.72.
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Bis Quinazolinones as Efficient Insecticides
METHOD OF BIOASSAY TECHNIQUE
MATERIALS AND METHODS
The leaf dipping technique was adopted on the 4th instar
larvae to simulate the actual treatments under field condi-
tions [19]. A stock solution of each chemical was freshly
prepared. Subsequent water dilution was made to achieve
concentrations of 100, 200, 400, and 800ppm. Discs of
5-cm diameter were made from cotton leaves collected
from unsprayed fields. The leaves were washed, dried,
immersed in a test solution for 10 s and allowed to dry on
corrugated kitchen foil at ambient temperature for
1–1.5h. Leaf discs immersed in distilled water as control
treatment. On drying, the leaf discs were placed in individ-
ual petri dishes (9-cm diameter). Each treatment (concen-
tration) was replicated 3 times, including water solvent
control. Ten of 4th instar larvae were placed on each leaf
disc (replication), and thus the total number of tested larvae
per concentration was 30. The bioassay was kept at
temperature 25 2°C and 65 5% relative humidity to
determine the different biological criteria. Mortality was
assessed after 72-h exposure to tested compounds; the
LC50 and toxicity index were also estimated.
The cotton leaf worm strain in the present study was
taken from field colony and reared in central agricultural
pesticide laboratory. This strain was obtained from Sharkia
governorate. The strain was kept under laboratory condi-
tions at 25 2°C and 65 5% relative humidity away from
any chemical pressure.
CHEMICALS USED
The newly synthesized quinazolinone derivatives.
Table 1 and Figures 2 and 3 showed the insecticidal
activity data of some synthesized quinazolinone deriva-
tives. These data revealed that as the concentration of
tested compound increases the insecticidal activity in-
creases. From this table we detected that the acetylating
quinazolinone derivative (8) was the more effective com-
pound where it recorded LC50 at 147.895ppm followed
by compounds (9), (7), (11), (5), (4), and (10) with LC50
160.687, 178.317, 283.418, 351.822, 353.589, and
917.032ppm, respectively. On the other hand compound
Table 1
The insecticidal activity of some synthesized quinazolinone derivatives.
Concentration ppm
100
200
400
800
LC50
Slope
Toxicity index
% mortality
4
5
6
7
8
9
10
11
6.67
16.67
0.0
33.33
40.0
36.67
23.33
3.33
26.67
33.33
16.67
53.33
56.67
56.67
43.33
16.67
50.0
50.0
30.0
70.0
76.67
73.33
60.0
30.0
86.67
76.67
43.33
93.33
100.0
90.0
353.589
351.822
1048.957
178.317
147.895
160.687
917.032
283.418
2.784
1.829
1.318
1.964
1.648
1.74
41.83
40.04
14.09
82.94
100
92.04
16.13
52.18
73.33
43.33
1.481
1.623
Figure 2. Ldp line of synthesized (4–7) quinazolinone derivatives.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

M. M. Elshahawi, A. K. EL-Ziaty, J. M. Morsy, and A. F. Aly
Vol 000
Figure 3. Ldp line of synthesized 8–11 quinazolinone derivatives.
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(6) was the least efficient compound among the other tested
quinazolinone derivatives against cotton leaf worm S.
littoralis insect where its LC50 is 1048.957ppm.
The tested quinazolinone derivatives are a new anthranilic
diamide insecticide, which effectively controls pest insects,
and has been shown to be effective against insects that have
developed resistance to older classes of chemistry.
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Journal of Heterocyclic Chemistry
DOI 10.1002/jhet