Design, synthesis and insecticidal evaluation of novel pyrazolecarboxamides containing cyano substituted N-pyridylpyrazole

Article abstract of DOI:10.1002/cjoc.201090296

12 Novel pyrazolecarboxamides containing cyano substituted N-pyridylpyrazole were synthesized, and their structures were characterized by ¹H NMR and HRMS techniques. Their evaluated insecticidal activities against oriental armyworm (Mythimna separata) indicated that the cyano-containing pyrazolecarboxamides exhibited moderate insecticidal activities. Compounds 6i and 6k showed comparable higher activity than corresponding anthranilic diamide 6m.

Full text of DOI:10.1002/cjoc.201090296

FULL PAPER
Design, Synthesis and Insecticidal Evaluation of Novel
Pyrazolecarboxamides Containing Cyano Substituted
N-Pyridylpyrazole†
Liu, Zhili(刘智力)
Feng, Qi(冯启)
Xiong, Lixia(熊丽霞)
Wang, Mingzhong(王明忠)
Li, Zhengming*(李正名)
State-Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry,
Nankai University, Tianjin 300071, China
12 novel pyrazolecarboxamides containing cyano substituted N-pyridylpyrazole were synthesized, and their
1
structures were characterized by H NMR and HRMS techniques. Their evaluated insecticidal activities against
oriental armyworm (Mythimna separata) indicated that the cyano-containing pyrazolecarboxamides exhibited mod-
erate insecticidal activities. Compounds 6i and 6k showed comparable higher activity than corresponding an-
thranilic diamide 6m.
Keywords cyano, insecticidal activity, N-pyridylpyrazole, anthranilic diamide, pyrazolecarboxamide
Introduction
The discovery of novel insecticide with a new mode
of action is crucial to overcome resistance and
eco-biological problems associated with some conven-
tional insecticides. The ryanodine receptors (RyR),
which regulates calcium ion channel in insect nerve
synpase, has represented one of the attractive biological
target for pest control strategies.1 The commercial
chlorantraniliprole (A),2,3 which has a typical anthranilic
diamide structure, was developed by DuPont Co. and
exhibited exceptional insecticidal activity on a broad
range of Lepidoptera, Coleoptera, Diptera and Isop-
tera. 4
Figure 1 Chemical structures of compounds A— C.
The anthranilic diamide structure has been charac-
teristic to chlorantraniliprole, yet the insecticidal activ-
ity of simpler structures that eliminate the aliphatic am-
ide moiety has been little reported. Pyrazolecarbox-
amide (B) reported by DuPont Co. with a simpler struc-
ture, still showed high activity against Lepidoptera.5
The introduction of a cyano group to replace the 4-halo
substituent led to the discovery of cyantraniliprole
(Cyazypyr, C),6 which had improved plant mobility and
increased spectra of insect control. In this article, based
on our previous work,7 a new cyano substituted
N-pyridylpyrazole carboxylic acid was synthesized.
Further derivatization of this compound led to 12 novel
pyrazolecarboxamides as shown in Scheme 1. The bio-
activity against oriental armyworm was tested accord-
ingly.
Experimental
Materials and instruments
1H NMR spectra were recorded at 400 MHz using a
Bruker AC-400 spectrometer in CDCl3 or DMSO-d6
solution with tetramethylsilane as the internal standard.
High-resolution mass spectrometry (HRMS) data were
obtained on a Varian QFT-ESI instrument. The melting
points were determined on an X-4 binocular microscope
melting point apparatus (Beijing Tech Instruments Co.,
Beijing, China) and were uncorrected. Yields were not
optimized. Reagents were all analytically or chemically
pure. Substituted anilines 5a—5l were purchased from
Alfa Aesar. All solvents and liquid reagent were dried
*
E-mail: nkzml@vip.163.com; Tel.: 0086-022-23505376; Fax: 0086-022-23505948
Received July 21, 2010; revised August 20, 2010; accepted August 23, 2010.
Project supported by the National Basic Research Program of China (No. 2010CB126106).
† Dedicated to the 60th Anniversary of Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences.
Chin. J. Chem. 2010, 28, 1757— 1760
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Liu et al.
FULL PAPER
Scheme 1 General synthetic procedure of compounds 6a— 6m
1-(3-Chloropyridin-2-yl)-5-(furan-2-yl)-1H-pyra-
zole-3-carbonitrile (3) The title compound was syn-
thesized according to the method reported by Saitoh et
al.9 Thionyl dichloride (2.0 mmol) was added dropwise
to an ice-cold solution of compound 2 (1.0 mmol) in 30
mL of DMF with the temperature maintained below 5
℃ throughout. The reaction was stirred at 5 ℃ for 45
min and then 2 h at ambient temperature. Then the mix-
ture was poured into 50 mL of ice water with stirring for
0.5 h and gray powder was precipitated. After filtration
and recrystallization, the title compound 3 was obtained
1
as white solid, yield 65.8%, m.p. 92—94 ℃; H NMR
(400 MHz, CDCl3) δ: 8.58 (d, J＝4.4 Hz, 1H, Ar-H),
7.99 (d, J＝8.0 Hz, 1H, Ar-H), 7.54 (dd, J＝4.8, 7.6 Hz,
1H, Ar-H), 7.37 (s, 1H, Ar-H), 7.04 (s, 1H, Ar-H), 6.36
(s, 1H, Ar-H), 6.00 (d, J＝3.2 Hz, 1H, Ar-H).
1-(3-Chloropyridin-2-yl)-3-cyano-1H-pyrazole-5-
carboxylic acid (4) The furan moiety was oxidized by
the procedure reported by Varnes et al.10 KMnO4 (5.0
mmol) and KH2PO4 (3.0 mmol) were added succe-
ssively to a solution of compound 3 (1.0 mmol) in 20
mL of acetone and 20 mL of water. The mixture was
refluxed for 1 h, then filtrated and washed with 20 mL
of hot water. The filtrate was acidified to pH 2, then
most of the acetone was evaporated in vacuo. The re-
sulting solution was extracted with ethyl acetate. Or-
ganic layer was combined and dried with sodium sulfate.
The solution was evaporated to give the crude product,
which was recrystallized with petroleum ether and ethyl
acetate (V∶V＝2∶1) to give the title carboxylic acid as
by standard methods in advance and distilled before use.
Chlorantraniliprole was synthesized according to the
literature8 and used as the control.
General procedure
The intermediate 1-(3-chloropyridin-2-yl)-5-(furan-
2-yl)-1H-pyrazole-3-carboxylic acid (1) was synthe-
sized according to our previous work.7 2-Amino-5-
chloro-N,3-dimethylbenzamide (5m) was synthesized
by the method reported by Dong et al.8 The title com-
pounds were prepared as shown in Scheme 1.
1
a yellow solid, yield 55.6%. m.p. 237—239 ℃; H
NMR (400 MHz, CDCl3) δ: 8.60 (d, J＝4.4 Hz, 1H,
Ar-H), 8.32 (d, J＝8.4 Hz, 1H, Ar-H), 7.83 (s, 1H,
Ar-H), 7.75 (dd, J＝4.8, 8.0 Hz, 1H, Ar-H).
General synthetic procedure of 6a— 6m Com-
pound 4 (0.5 mmol) was dissolved in 20 mL of di-
chloromethane under stirring, oxalyl chloride (0.8 mmol)
and a drop of DMF were added successively. After stir-
ring for 2 h at room temperature, dichloromethane was
removed in vacuo. The residue was dissolved in 20 mL
of dichloromethane, and then added dropwise to an
ice-cold solution of substituted anilines 5a—5m (0.5
mmol), pyridine (0.5 mmol) in 20 mL of dichloro-
methane. The mixture was stirred at room temperature
for 2 h before it was washed with 2 mol/L hydrochloric
acid, saturated sodium bicarbonate solution and brine
successively. The organic layer was dried with sodium
sulfate and evaporated. The residue was subjected to
flash chromatography on silica gel with V(petroleum
ether)∶V(ethyl acetate)＝1∶1 to give the title com-
pounds 6a—6m.
1-(3-Chloropyridin-2-yl)-5-(furan-2-yl)-1H-pyra-
zole-3-carboxamide (2) Compound 1 (1.0 mmol) was
dissolved in 25 mL of dichloromethane. Under vigorous
stirring, oxalyl chloride (1.5 mmol) and a drop of DMF
were added successively. After stirring at room tem-
perature for 3 h, the mixture was evaporated to dryness
in vacuo. The residue was dissolved in 10 mL of THF,
and added dropwise to an ice-cold solution of ammo-
nium hydroxide (0.5 mL) in 10 mL of THF. After com-
pletion, the mixture was left to warm to ambient tem-
perature and stirred for another 40 min. Then the yellow
suspension was poured into 50 mL of water and ex-
tracted by ethyl acetate (30 mL×3). The combined ex-
tracts were washed with 2 mol/L hydrochloric acid and
brine successively. The yellow solution was dried and
evaporated to give the title compound as a yellow solid,
1
1
6a: Yield 75.0%; white solid, m.p. 209—211 ℃; H
yield 85.0%. m.p. 151—153 ℃; H NMR (400 MHz,
4
NMR (400 MHz, CDCl3) δ: 8.53 ( d, J＝4.8 Hz, 1H,
Ar-H), 8.36 (s, 1H, CONH), 8.22 (d, J＝8.0 Hz, 1H,
Ar-H), 7.97 (d, J＝8.4 Hz, 1H, Ar-H), 7.51 (dd, J＝4.6,
7.6 Hz, Ar-H), 7.41 (d, J＝8.0 Hz, 1H, Ar-H), 7.29 (s,
1H, Ar-H), 7.26—7.23 (m, 1H, Ar-H), 7.11 (t, J＝7.8
Hz, 1H, Ar-H). HRMS calcd for C16H9Cl2N5O ([M－
CDCl3) δ: 8.59 (dd, J＝1.6 Hz, J＝4.8 Hz, 1H, Ar-H),
4
7.97 (dd, J＝1.4 Hz, J＝8.2 Hz, 1H, Ar-H), 7.52 (dd,
J＝4.4, 8.0 Hz, Ar-H), 7.32 (d, J＝1.6 Hz, 1H, Ar-H),
7.21 (s, 1H, Ar-H), 6.84 (s, 1H, CONH), 6.34 (dd, J＝
1.8, 3.4 Hz, 1H, Ar-H), 6.05 (s, 1H, Ar-H), 5.67(s, 1H,
CONH).
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Chin. J. Chem. 2010, 28, 1757— 1760

Design, Synthesis and Insecticidal Evaluation of Novel Pyrazolecarboxamides
H]－ ) 356.0111, found 356.0113.
2H, Ar-H), 7.33 (s, 1H, Ar-H). HRMS calcd for C16H7-
6b: Yield 90.9%; white solid, m.p. 185—187 ℃; 1H
Cl4N5O ([M－H]－ ) 423.9332, found 423.9328.
4
1
NMR (400 MHz, CDCl3) δ: 8.47 (dd, J＝2.0 Hz, J＝
6j: Yield 60.7%; white solid, m.p. 165—167 ℃; H
NMR (400 MHz, CDCl3) δ: 8.68 (s, 1H, CONH), 8.53
(d, J＝4.8 Hz, 1H, Ar-H), 7.99 (d, J＝8.0 Hz, 1H,
Ar-H), 7.78—7.76 (m, 1H, Ar-H), 7.52 (dd, J＝4.8, 8.4
Hz, 1H, Ar-H), 7.36 (s, 1H, Ar-H), 6.97—6.90 (m, 1H,
Ar-H). HRMS calcd for C16H7ClF3N5O ([M－H]－ )
376.0219, found 376.0219.
4
6.4 Hz, 1H, Ar-H), 7.92 (dd, J＝2.0 Hz, J＝11.8 Hz,
1H, Ar-H), 7.88 (s, 1H, CONH), 7.53 (d, J＝9.6 Hz, 1H,
Ar-H), 7.45 (dd, J＝6.4, 10.8 Hz, 1H, Ar-H), 7.19—
7.15 (m, 4H, Ar-H), 2.24 (s, 3H, Ar-CH3). HRMS calcd
for C17H12ClN5O ([M—H]－ ) 336.0658, found 336.0666.
6c: Yield 55.0%; white solid, m.p. 200—202 ℃; 1H
NMR (400 MHz, DMSO-d6) δ: 10.77 (s, 1H, CONHAr),
8.55 (d, J＝4.4 Hz, 1H, Ar-H), 8.40 (d, J＝7.6 Hz, 1H,
Ar-H), 7.89 (s, 1H, Ar-H), 7.79 (d, J＝7.6 Hz, 1H,
Ar-H), 7.74—7.67 (m, 2H, Ar-H), 7.56 (t, J＝7.6 Hz,
6k: Yield 68.5%; white solid, m.p. 180—182 ℃; 1H
NMR (400 MHz, CDCl3) δ: 8.49 (d, J＝4.4 Hz, 1H,
Ar-H), 7.92 (d, J＝8.0 Hz, 1H, Ar-H), 7.82 (s, 1H,
CONH), 7.46 (dd, J＝4.4, 7.6 Hz, 1H, Ar-H), 7.32 (s,
1H, Ar-H), 7.19 (d, J＝7.2 Hz, 1H, Ar-H), 6.89 (t, J＝
8.6 Hz, 1H, Ar-H). HRMS calcd for C16H7BrClF2N5O
([M－H]－ ) 435.9418, found 435.9418.
1H, Ar-H), 7.43 (d, J＝7.6 Hz, 1H, Ar-H). HRMS calcd
－
for C17H9ClF3N5O ([M — H] ) 390.0375, found
390.0371.
6d: Yield 93.3%; white solid, m.p. 209—212 ℃; 1H
NMR (400 MHz, DMSO-d6) δ: 10.35 (s, 1H, CONHAr),
8.55 (d, J＝4.4 Hz, 1H, Ar-H), 8.24 (d, J＝8.0 Hz, 1H,
Ar-H), 7.88 (s, 1H, Ar-H), 7.67 (dd, J＝4.8, 8.0 Hz, 1H,
Ar-H), 7.14—7.08 (m, 3H, Ar-H), 2.14 (s, 6H, Ar-CH3).
HRMS calcd for C18H14ClN5O ([M—H]－ ) 350.0814,
found 350.0819.
6l: Yield 80.4%; white solid, m.p. 167—169 ℃; H
1
NMR (400 MHz, DMSO-d6) δ: 10.81 (s, 1H, CONHAr),
4
8.56 (dd, J＝1.2 Hz, J＝4.8 Hz, 1H, Ar-H), 8.30 (dd,
4J＝1.0 Hz, J＝8.0 Hz, 1H, Ar-H), 7.93 (s, 1H, Ar-H),
7.72 (dd, J＝4.4, 8.0 Hz, 1H, Ar-H), 7.68 (d, J＝8.8 Hz,
2H, Ar-H), 7.43 (d, J＝8.8 Hz, 2H, Ar-H). HRMS calcd
for C16H9ClIN5O ([M－H]－ ) 447.9468, found 447.9464.
6m: Yield 65.8%; white solid, m.p. 220—222 ℃
6e: Yield 60.4%; white solid, m.p. 212—213 ℃; 1H
NMR (400 MHz, DMSO-d6) δ: 10.98 (s, 1H, CONHAr),
8.55 (d, J＝4.8 Hz, 1H, Ar-H), 8.24 (d, J＝8.0 Hz, 1H,
Ar-H), 7.92 (s, 1H, Ar-H), 7.69 (dd, J＝4.6, 8.0 Hz, 1H,
Ar-H), 7.57 (d, J＝8.0 Hz, 2H, Ar-H), 7.40 (t, J＝8.0
Hz, 1H, Ar-H). HRMS calcd for C16H8Cl3N5O ([M—
H]－ ) 389.9733, found 389.9728.
1
(lit.11 m.p. 182—184 ℃); H NMR (400 MHz, CDCl3)
δ: 10.34 (s, 1H, CONHAr), 8.49 (dd, 4J＝1.4 Hz, J＝4.6
4
Hz, 1H, Ar-H), 7.91 (dd, J＝1.4 Hz, J＝8.0 Hz, 1H,
Ar-H), 7.50 (s, 1H, Ar-H), 7.72 (dd, J＝4.6, 8.2 Hz, 1H,
Ar-H), 7.25 (d, 4J＝2.0 Hz, 1H, Ar-H), 7.23 (d, 4J＝2.0
Hz, 1H, Ar-H), 6.15 (d, J＝4.8 Hz, 1H, CONHCH3),
2.96 (d, J＝4.8 Hz, 3H, CONHCH3), 2.17 (s, 3H,
Ar-CH3).
1
6f: Yield 75.2%; white solid, m.p. 173—174 ℃; H
NMR (400 MHz, DMSO-d6) δ: 10.46 (s, 1H, CONHAr),
4
8.55 (dd, J＝1.2 Hz, J＝4.8 Hz, 1H, Ar-H), 8.26 (dd,
4J＝1.2 Hz, J＝8.0 Hz, 1H, Ar-H), 7.91 (s, 1H, Ar-H),
Biological activity
Insecticidal activities against oriental armyworm
(Mythimna separata) were performed in the greenhouse.
The bioassay was operated at (25±1) ℃ according to
statistical requirements. Assessments were made on a
dead/alive basis, and mortality rates were corrected ac-
cording to Abbott’s formula.12 Percent mortality was
evaluated. Error of the experiments was 5%. For com-
parative purpose, compound 6m11 and chlorantrani-
liprole were tested as control under the same conditions.
The insecticidal activities of compounds 6a—6m
and chlorantraniliprole were evaluated using the re-
ported procedure.8 The insecticidal activity against ori-
ental armyworm was tested by foliar application, indi-
vidual corn leaves were placed on moistened pieces of
filter paper in Petri dishes. The leaves were then sprayed
with the test solution and allowed to dry. Then every 10
fourth-instar oriental armyworm larvae were put into
each dish. Percent mortalities were evaluated 2 d after
treatment. Each treatment was replicated for three times.
7.70 (dd, J＝4.6, 8.2 Hz, 1H, Ar-H), 7.36 (s, 1H, Ar-H),
7.25 (s, 2H, Ar-H), 2.18 (s, 3H, Ar-CH3). HRMS calcd
－
for C17H11Cl2N5O ([M － H] ) 370.0268, found
370.0272.
1
6g: Yield 45.7%; white solid, m.p. 98—101 ℃; H
4
NMR (400 MHz, CHCl3) δ: 8.50 ( dd, J＝2.0 Hz, J＝
6.4 Hz, 1H, Ar-H), 8.20 (s, 1H, CONH), 8.10 (s, 1H,
Ar-H), 8.03—8.02 (m, 2H, Ar-H), 7.98 (dd, 4J＝2.0 Hz,
J＝10.8 Hz, 1H, Ar-H), 7.51 (dd, J＝6.0, 10.8 Hz, 1H,
Ar-H), 7.34 (s, 1H, Ar-H), 2.41 (s, 3H, Ar-CH3). HRMS
calcd for C17H11ClN6O3 ([M—H]－ ) 381.0508, found
381.0507.
6h: Yield 48.0%; white solid, m.p. 202—204 ℃; 1H
NMR (400 MHz, DMSO-d6) δ: 10.87 (s, 1H, CONHAr),
4
8.56 (dd, J＝1.2 Hz, J＝4.8 Hz, 1H, Ar-H), 8.26 (dd,
4J＝1.2 Hz, J＝8.0 Hz, 1H, Ar-H), 8.27 (d, J＝1.2 Hz,
4
J＝8.0 Hz, 1H, Ar-H), 7.97 (s, 1H, Ar-H), 7.93 (s, 1H,
Ar-H), 7.78 (s, 1H, Ar-H), 7.70 (dd, J＝4.8, 8.2 Hz, 1H,
Ar-H). HRMS calcd for C16H7Cl4N5O ([M — H] － )
423.9932, found 423.9331.
1
6i: Yield 50.4%; white solid, m.p. 187—189 ℃; H
Results and discussion
NMR (400 MHz, CHCl3) δ: 8.48 (d, J＝4.8 Hz, 1H,
Ar-H), 7.92 (d, J＝8.0 Hz, 1H, Ar-H), 7.91 (s, 1H,
CONH), 7.46 (dd, J＝4.8, 8.0 Hz, 1H, Ar-H), 7.38 (s,
Insecticidal activity
The insecticidal activities of compounds 6a—6m
Chin. J. Chem. 2010, 28, 1757— 1760
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Liu et al.
FULL PAPER
and chlorantraniliprole against oriental armyworm was
summarized in Table 1.
but still lower than chlorantraniliprole.
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Table 1 Insecticidal activities of compounds 6a— 6m and
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100
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0
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50
60
100
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2-CH3,4-Cl
2-CH3,4-NO2
2,4,5-Cl3
0
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5
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6h
6i
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2,4,6-Cl3
100
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6j
2,3,4-F3
6k
6l
2,4-F2,6-Br
100
0
100
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100
In general, different substitutes in the benzene ring
suggested the activity sequence as 2,4,6-substituted (6i
and 6k)＞2,6- or 2,4-substituted (6d—6h)＞monosub-
stituted (6a—6c and 6l). The 2,3,5-trichloro substituted
compound 6h showed the activity of 100% at 100 mg/L,
but the 2,3,4-trifluro substituted compound 6g had no
effect at the test concentration. Surprisingly, compounds
6i and 6k showed comparable higher activity than the
corresponding cyano-containing anthranilic diamide 6m,
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Chin. J. Chem. 2010, 28, 1757— 1760