RSC Advances
Paper
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off, and residue was puried by column chromatography on
Analytical data for 91h. Yield: 34%; m.p. 184–186 C; H NMR
silica gel with petroleum ether and ethyl acetate (v/v ¼ 4 : 1) to (500 MHz, CDCl ): d 7.99 (s, 1H, Ph–CH]N–), 7.62 (d, J ¼ 15.9
3
give 91b as a yellow solid. Yield: 62.8 mg (68% of theory); m.p. Hz, 1H, Ar–CH]CH), 7.47–7.45 (m, 3H, Ph–H), 7.35 (d, J ¼ 1.6
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1
1
80–185 C; H NMR (500 MHz, CDCl ): d 8.02 (s, 1H, Ph–CH] Hz, 1H, Ph–H), 7.22 (d, J ¼ 7.95 Hz, 1H, Ph–H), 6.92–6.90 (m,
3
N–), 7.50–7.48 (m, 1H, Ph–H), 7.31 (d, J ¼ 1.55 Hz, 1H, Ph–H), 2H, Ph–H), 6.52 (s, 1H, –NH–), 6.24 (d, J ¼ 15.75 Hz, 1H, Ar–
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.24 (d, J ¼ 8.0 Hz, 1H, Ph–H), 6.60 (s, 1H, –NH–), 3.95 (s, 3H, ] CH]CH), 3.92 (s, 3H, ]N–OCH ), 3.86 (s, 3H, Ar–OCH ), 3.40
3
3
N–OCH
3
), 3.40 (s, 3H, –OCH
3
), 3.26–3.22 (m, 1H, CH
3
3 3
OCH–), (s, 3H, –OCH ), 3.25–3.23 (m, 1H, CH OCH–), 2.33 (s, 3H, Me–
1
3
2
3
3
.30 (s, 3H, Me–Ar), 2.23–1.40 (m, 8H, cyclohexane-H
H, O]C–CH
8
), 2.08 (s, Ar), 2.25–1.41 (m, 8H, cyclohexane-H8); C NMR (125 MHz,
3
); TOF-MS: calcd for C21
H
26
N
2
O
5
386.1842, found CDCl ): d 169.9, 165.6, 162.2, 161.9, 148.5, 148.2, 139.4, 130.8,
3
86.1843.
130.3, 129.6, 129.3, 128.5, 126.8, 126.3, 121.9, 114.5, 112.1, 61.8,
5
.1.6 The identical method of 91b was used to synthesize 60.7, 55.9, 55.5, 31.9, 28.5, 21.5, 19.8. TOF-MS: calcd for
and purify compounds 91c–91k
C H N O 504.2260, found 504.2265.
Analytical data for 91c. Yield: 35%; H NMR (500 MHz,
2
9
32 2 6
1
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1
Analytical data for 91i. Yield: 29%; m.p. 159–161 C; H NMR
CDCl
3
): d 8.01 (s, 1H, Ph–CH]N–), 7.48–7.46 (d, J ¼ 8.0 Hz, 1H, (500 MHz, CDCl ): d 8.01 (s, 1H, Ph–CH]N–), 7.63 (d, J ¼ 16 Hz,
3
Ph–H), 7.31 (s, 1H, Ph–H), 7.25–7.23 (d, J ¼ 8.0 Hz, 1H, Ph–H), 1H, Ph–CH]CH–), 7.51–7.49 (m, 2H, Ph–H), 7.05–7.03 (m, 3H,
6.71 (s, 1H, Ph–H), 3.96 (s, 3H, ]N–OCH
3
), 3.67–3.63 (m, 1H, Ph–H), 6.97 (d, J ¼ 2.0 Hz, 2H, Ph–H), 6.54 (s, 1H, –NH–), 6.33 (d,
CH ]CH–), 3.39 (s, 3H, –OCH ), 3.25–3.21 (m, 1H, CH
2
3
3
OCH–), J ¼ 16 Hz, 2H, Ph–CH]CH–), 3.94 (s, 3H, ]N–OCH ), 3.39 (s,
3
2.84–2.80 (m, 2H, CH ]CH–), 2.30 (s, 3H, Me–Ar), 2.23–1.40 (m, 3H, –OCH ), 3.27–3.22 (m, 1H, CH OCH–), 2.35 (s, 3H, Me–Ar),
2
3
3
8
H, cyclohexane-H ); TOF-MS: calcd for C H N O 398.1842, 2.22–1.38 (m, 8H, cyclohexane-H8); TOF-MS: calcd for
8 22 26 2 5
found 398.1838.
28 29 2 5
C H FN O 492.2061, found 492.2066.
Analytical data for 91j. Yield: 30%; H NMR (500 MHz, CDCl ):
3
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1
1
Analytical data for 91d. Yield: 38%; m.p. 192–194 C; H NMR
500 MHz, CDCl ): d 8.01 (s, 1H, Ph–CH]N–), 7.87–7.85 (m, d 8.00 (s, 1H, Ph–CH]N–), 7.50–7.48 (m, 1H, Ph–H), 7.46–7.37
H, Ph–H), 7.43 (dd, J ¼ 1.7 Hz, 1H, Ph–H), 7.37 (d, J ¼ 1.6 (m, 7H, Ph–H), 7.24 (d, J ¼ 8.0 Hz, 1H, Ph–H), 6.32 (s, 1H, –NH–),
¼ J
Hz, 1H, Ph–H), 7.23 (d, J ¼ 8.0 Hz, 2H, Ph–H), 7.18 (d, J ¼ 8.0 3.92 (s, 3H, ]N–OCH ), 3.40 (s, 3H, –OCH ), 3.28–3.24 (m, 1H,
(
2
3
1
2
3
3
Hz, 1H, Ph–H), 6.62 (s, 1H, –NH–), 3.93 (s, 3H, ]N–OCH
3
3
), 3.38 CH OCH–), 2.35 (s, 3H, Me–Ar), 2.27–1.41 (m, 8H, cyclohexane-
(
s, 3H, –OCH ), 3.23–3.21 (m, 1H, CH OCH–), 2.43 (s, 3H, Me– H8), 2.05–2.04 (m, 3H, O]C–CH3); TOF-MS: calcd for
3
3
1
3
Ar), 2.33 (s, 3H, Me–Ar), 2.24–1.43 (m, 8H, cyclohexane-H8);
NMR (125 MHz, CDCl ): d 170.1, 165.6, 161.5, 148.45, 147.34,
C
29 32 2 5
C H N O 488.2311, found 488.2316.
Analytical data for 91k. Yield: 36%; m.p. 173–174 C; H NMR
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1
3
1
1
1
C
45.4, 139.82, 139.37, 130.7, 130.6, 130.5, 130.3, 129.7, 129.6, (500 MHz, CDCl ): d 8.01 (s, 1H, Ph–CH]N–), 7.48–7.45 (m,
29.5, 129.4, 129.2, 128.6, 127.4, 126.6, 126.2, 124.9, 122.2, 1H, Ph–H), 7.31–7.01 (m, 7H, Ph–H), 6.55 (s, 1H, –NH–), 3.95 (s,
3
19.9, 61.9, 60.9, 55.7, 31.9, 28.3, 21.8, 19.8; TOF-MS: calcd for 3H, ]N–OCH ), 3.40 (s, 3H, –OCH ), 3.12–3.08 (m, 1H,
3
3
27
H
30
N
2
O
5
462.2155, found 462.2157.
CH OCH–), 2.84–2.81 (m, 2H, Ph–CH –CH –), 2.71–2.68 (m,
3 2 2
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1
Analytical data for 91e. Yield: 42%; m.p. 199–201 C; H NMR 2H, Ph–CH –CH –), 2.29 (s, 3H, Me–Ar), 2.14–1.27 (m, 8H,
2
2
(
500 MHz, CDCl ): d 8.03 (s, 1H, Ph–CH]N–), 7.72–7.70 (m, 1H, cyclohexane-H ); TOF-MS: calcd for C H N O 476.2311,
3
8 28 32 2 5
Ph–H), 7.53–7.51 (m, 1H, Ph–H), 7.43 (dd, J ¼ J ¼ 1.65 Hz, 1H, found 476.2316.
1
2
Ph–H), 7.40 (d, J ¼ 1.45 Hz, 1H, Ph–H), 7.22–7.20 (m, 1H, Ph–H),
.98–6.96 (m, 2H, Ph–H), 6.54 (s, 1H, –NH–), 3.94 (s, 3H, ]N–
OCH ), 3.87 (s, 3H, Ar–OCH ), 3.39 (s, 3H, –OCH ), 3.23–3.21 (m,
H, CH OCH–), 2.35 (s, 3H, Me–Ar), 2.24–1.40 (m, 8H, cyclo- All bioassays were performed on representative organisms
hexane-H
78.2102.
6
5.2 Biological assay
3
3
3
1
3
8
); TOF-MS: calcd for C27
H
30
N
2
O
6
478.2104, found reared in the laboratory. The bioassay was tested for triplicates
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at 25 ꢃ 1 C to take consideration of inter-batch variability. The
1
Analytical data for 91f. Yield: 39%; H NMR (500 MHz, CDCl ): variation of the measurement estimated over the total proce-
3
d 7.96 (s, 1H, Ph–CH]N–), 7.49–7.46 (m, 3H, Ph–H), 7.38–7.36 dure is known to be approximately ꢃ5%. Assessments were
m, 1H, Ph–H), 7.21–7.19 (m, 2H, Ph–H), 7.08–7.06 (m, 2H, Ph– made on a dead/alive basis, and mortality rates were corrected
H), 6.47 (s, 1H, –NH–), 3.97 (s, 3H, ]N–OCH ), 3.62 (s, 2H, Ph– using Abbott's formula. Evaluations were based on a percentage
CH –COO–), 3.38 (s, 3H, –OCH ), 3.22–3.20 (m, 1H, CH OCH–), scale of 0–100, where 0 indicates no activity and 100 represents
.33 (s, 3H, Me–Ar), 2.14–1.34 (m, 8H, cyclohexane-H
calcd for C27 462.2155, found 462.2166.
(
3
2
3
3
2
8
); TOF-MS: total kill. Spirotetramat was evaluated employing the same
procedure as standard.
30 2 5
H N O
1
Analytical data for 91g. Yield: 30%; H NMR (500 MHz,
5.2.1 Inhibition activity against bean aphids (Aphis fabae).
CDCl ): d 7.95 (s, 1H, Ph–CH]N–), 7.48–7.42 (m, 1H, Ph–H), The insecticidal activities of target compounds and spirote-
3
7
.26–7.16 (m, 4H, Ph–H), 7.08–7.06 (m, 1H, Ph–H), 6.94–6.92 tramat were evaluated according to the previously reported
33,34
(m, 1H, Ph–H), 6.54 (s, 1H, –NH–), 3.96 (s, 3H, ]N–OCH ), 3.57 procedure.
Bean aphids were treated according to a slightly
), 3.26–3.19 (m, 1H, modied FAO dip test. Tender soybean shoots with y healthy
3
OCH–), 2.34 (s, 3H, Me–Ar), 2.23 (s, 3H, Me–Ar), 2.18–1.38 third-instar nymphae were dipped into the diluted solutions of
3
2 3
(s, 2H, Ph–CH –COO–), 3.38 (s, 3H, –OCH
CH
(
4
m, 8H, cyclohexane-H
76.2311, found 476.2309.
8
); TOF-MS: calcd for C28
H
32
N
2
O
5
the compounds for 5 s, then superuous uid was removed,
and the nymphae treated were placed in an conditioned room.
Mortality was calculated 72 h aer treatment. Each treatment
49202 | RSC Adv., 2015, 5, 49195–49203
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