Design, Synthesis, and Insecticidal Activity of 1,5-Diphenyl-1-pentanone Analogues
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oxadiazinan-4-ylidene}nitramide (X12): White powdery
crystals, yield 28.2%, m.p. 147—148 ℃; H NMR
(CDCl3, 300 MHz) δ: 1.33—1.37 (m, 3H, CCH3), 2.37
(s, 3H, ArCH3), 3.64—3.76 (m, 2H, CH2C), 4.92 (s, 2H,
OCH2N), 5.36 (s, 2H, NCH2O), 6.93 (d, J=15.39 Hz,
1H, =CHC=O), 7.20—7.23 (m, 1H, ArH-2), 7.24—
7.30 (m, 1H, ArH-4), 7.36—7.38 (m, 2H, ArH-5,6),
7.83 (d, J=15.48 Hz, 1H, CH=C); IR (KBr) ν: 2945,
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crystals, yield 22.4%, m.p. 172—174 ℃; H NMR
(CDCl3, 300 MHz) δ: 1.26 (t, J=7.20 Hz, 3H, CCH3),
3.69—3.73 (m, 3H, CH2C), 4.93 (s, 2H, OCH2N), 5.37
(s, 2H, NCH2O), 6.96 (d, J=15.39 Hz, 1H, =CHC=
O), 7.44 (d, J=8.49 Hz, 2H, ArH-2,6), 7.52 (d, J=8.55
Hz, 2H, ArH-3,5), 7.78 (d, J=15.48 Hz, 1H, CH=C);
IR (KBr) ν: 3076, 1702, 1628, 1589, 1570, 1226, 1092
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1676, 1611, 1562, 1506, 1272, 1039 cm . Anal. calcd
for C15H18N4O4: C 56.60, H 5.70, N 17.60; found C
56.60, H 5.58, N 17.68.
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cm . Anal. calcd for C14H15ClN4O4: C 49.64, H 4.46,
N 16.54; found C 49.69, H 4.35, N 16.63.
N-{3-[(E)-3-(4-Bromophenyl)acryloyl]-5-ethyl-1,3,5-
oxadiazinan-4-ylidene}nitramide (X13): White powdery
N-(3-Cinnamoyl-5-ethyl-1,3,5-oxadiazinan-4-yli-
dene)nitramide (X18): Yellow powdery crystals, yield
18.3%, m.p. 168—170 ℃.; 1H NMR (CDCl3, 300 MHz)
δ: 1.35 (t, J=7.26 Hz, 3H, CCH3), 3.65—3.69 (m, 2H,
CH2C), 4.92 (s, 2H, OCH2N), 5.36 (s, 2H, NCH2O),
6.96 (d, J=15.39 Hz, 1H, =CHC=O), 7.37—7.41 (m,
3H, ArH-2,3,4), 7.55—7.58 (m, 2H, ArH-5,6), 7.86 (d,
J=15.39 Hz, 1H, CH=C); IR (KBr) ν: 3081, 1678,
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crystals, yield 25.0%, m.p. 174—176 ℃; H NMR
(CDCl3, 300 MHz) δ: 1.36 (t, J=7.20 Hz, 3H, CCH3),
3.65—3.76 (m, 2H, CH2C), 4.93 (s, 2H, OCH2N), 5.37
(s, 2H, NCH2O), 6.94 (d, J=15.39 Hz, 1H, =CHC=
O), 7.26—7.38 (m, 2H, ArH-2,6), 7.48—7.52 (m, 2H,
ArH-3,5), 7.80 (d, J=15.48 Hz, 1H, CH=C); IR (KBr)
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ν: 3077, 1700, 1628, 1586, 1486, 1295, 1071 cm .
Anal. calcd for C14H15BrN4O4: C 43.88, H 3.95, N
14.62; found C 43.80, H 3.94, N 14.63.
1614, 1568, 1271, 1503, 1040 cm . Anal. calcd for
C14H16N4O4: C 55.26, H 5.30, N 18.41; found C 55.25,
H 5.22, N 18.69.
N-{3-[(E)-3-(2,4-Dichlorophenyl)acryloyl]-5-ethyl-
1,3,5-oxadiazinan-4-ylidene}nitramide (X14): White
N-{3-Ethyl-5-[(E)-3-(furan-2-yl)acryloyl]-1,3,5-
oxadiazinan-4-ylidene}nitramide
(X19):
Brown
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powdery crystals, yield 45.5%, m.p. 139—140 ℃; H
powdery crystals, yield 19.8%, m.p. 131—133 ℃; H
NMR (CDCl3, 300 MHz) δ: 1.34 (t, J=7.22 Hz, 3H,
CCH3), 3.65 — 3.68 (m, 3H, CH2C), 4.91 (s, 2H,
OCH2N), 5.34 (s, 2H, NCH2O), 6.47—6.49 (m, 1H,
Fu-3 H) , 6.71 (d, J=3.45 Hz, 1H, Fu-4 H), 6.82 (d, J=
15.03 Hz, 1H, =CHC=O), 7.48—7.52 (m, 1H, Fu-5
H), 7.59 (d, J=15.06 Hz, 1H, CH=C); IR (KBr) ν:
NMR (CDCl3, 300 MHz) δ: 1.36 (t, J=7.20 Hz, 3H,
CCH3), 3.65 — 3.76 (m, 2H, CH2C), 4.93 (s, 2H,
OCH2N), 5.37 (s, 2H, NCH2O), 6.94 (d, J=15.39 Hz,
1H, =CHC=O), 7.24 (d, J=8.52 Hz, 1H, ArH-5),
7.43 (d, J=2.07 Hz, 1H, ArH-2), 7.63 (d, J=8.52 Hz,
1H, ArH-4), 7.80 (d, J=15.48 Hz, 1H, CH=C); IR
(KBr) ν: 3083, 1708, 1625, 1584, 1504, 1228, 1050
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3093, 1675, 1613, 1567, 1273, 1040 cm . Anal. calcd
for C12H14N4O5: C 48.98, H 4.80, N 19.04; found C
48.91, H 4.63, N 19.09.
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cm . Anal. calcd for C14H14Cl2N4O4: C 45.06, H 3.78,
N 15.01; found C 45.11, H 3.74, N 15.10.
N-{3-Ethyl-5-[(E)-3-(4-methoxyphenyl)acryloyl]-
1,3,5-oxadiazinan-4-ylidene}nitramide (X15): Yellow
N-{3-Ethyl-5-[(E)-3-(thiophen-2-yl)acryloyl]-1,3,5-
oxadiazinan-4-ylidene}nitramide
(X20):
Brown
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powdery crystals, yield 17.2%, m.p. 142—144 ℃; H
powdery crystals, yield 15.2%, m.p. 165—167 ℃; H
NMR (CDCl3, 300 MHz) δ: 1.35 (t, J=7.22 Hz, 3H,
CCH3), 3.65 — 3.69 (m, 3H, CH2C), 4.92 (s, 2H,
OCH2N), 5.35 (s, 2H, NCH2O), 6.74 (d, J=15.06 Hz,
1H, =CHC=O), 7.03—7.09 (m, 1H, Thiophene-4 H),
7.34 (d, J=3.41 Hz, 1H, Thiophene-3 H), 7.44 (d, J=
5.10 Hz, 1H, Thiophene-5 H), 7.94 (d, J=15.09 Hz, 1H,
CH=C); IR (KBr) ν: 3119, 1674, 1599, 1566, 1280,
NMR (CDCl3, 300 MHz) δ: 1.35 (t, J=7.22 Hz, 3H,
CCH3), 3.66—3.68 (m, 2H, CH2C), 3.84 (s, 3H, OCH3),
4.96 (s, 2H, OCH2N), 5.36 (s, 2H, NCH2O), 6.80—6.91
(m, 3H, =CHC=O, ArH-2,6), 7.51—7.54 (m, 2H,
ArH-3,5), 7.83 (d, J=15.32 Hz, 1H, CH=C); IR (KBr)
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ν: 3081, 1674, 1602, 1569, 1515, 1308, 1027 cm .
Anal. calcd for C15H18N4O5: C 53.89, H 5.43, N 16.76;
found C 53.76, H 5.49, N 16.61.
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1043 cm . Anal. calcd for C12H14N4O4S: C 46.44, H
N-{3-[(E)-3-(4-Ethoxyphenyl)acryloyl]-5-ethyl-1,3,5-
4.55, N 18.05; found C 46.40, H 4.41, N 18.12.
oxadiazinan-4-ylidene}nitramide
(X16):
Yellow
N-{3-[(E)-3-(4-Fluorophenyl)acryloyl]-5-isopropyl-
1,3,5-oxadiazinan-4-ylidene}nitramide (X21): White
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powdery crystals, yield 22.3%, m.p. 126—128 ℃; H
NMR (CDCl3, 300 MHz) δ: 1.35 (t, J=7.22 Hz, 3H,
CCH3), 1.43 (t, J=7.02 Hz, 3H, OCCH3), 3.64—3.68
(m, 2H, CH2C), 4.04—4.08 (m, 2H, OCH2), 4.91 (s, 2H,
OCH2N), 5.35 (s, 2H, NCH2O), 6.80—6.89 (m, 3H,
=CHC=O, ArH-2,6), 7.49—7.52 (m, 2H, ArH-3,5),
7.82 (d, J=15.36 Hz, 1H, CH=C); IR (KBr) ν: 3081,
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powdery crystals, yield 45.5%, m.p. 131—132 ℃; H
NMR (CDCl3, 300 MHz) δ: 1.33 (d, J=6.84 Hz, 6H,
C(CH3)2), 4.78—4.82 (m, 1H, CHC2), 4.86 (s, 2H,
OCH2N), 5.34 (s, 2H, NCH2O), 6.89 (d, J=15.39 Hz,
1H, =CHC=O), 7.04—7.10 (m, 2H, ArH-2,6), 7.53—
7.58 (m, 2H, ArH-3,5), 7.82 (d, J=15.39 Hz, 1H, CH=
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1696, 1600, 1570, 1512, 1294, 1040 cm . Anal. calcd
for C16H20N4O5: C 55.17, H 5.79, N 16.08; found C
55.07, H 5.63, N 16.00.
C); IR (KBr) ν: 3110, 1674, 1617, 1597, 1544, 1240,
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1006 cm- . Anal. calcd for C15H17FN4O4: C 53.57, H
5.09, N 16.66; found C 53.60, H 4.93, N 16.78.
N-[3-Ethyl-5-((E)-3-m-tolylacryloyl)-1,3,5-oxadia-
zinan-4-ylidene]nitramide (X17): Yellow powdery
N-{3-[(E)-3-(4-Chlorophenyl)acryloyl]-5-isopropyl-
1,3,5-oxadiazinan-4-ylidene}nitramide (X22): White
Chin. J. Chem. 2011, 29, 2394— 2400
© 2011 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
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