Synthesis and biological activity of novel N-(3-furan-2-yl-1-phenyl-1H-pyrazol-5-yl) amides derivatives

Article abstract of DOI:10.1016/j.cclet.2016.06.019

A series of novel N-(3-furan-2-yl-1-phenyl-1H-pyrazol-5-yl) amides derivatives were designed and synthesized. Their structures were confirmed by¹H NMR,¹³C NMR and HRMS. All title compounds were evaluated for their herbicidal and antifungal activities. Preliminary bioassay results indicated that the title compounds showed good to moderate herbicidal activity at 1000?mg/L. Compound 6q presented the best activity against Digitaria sanguinalis (L) Scop., Amaranthus retroflexus L. and Arabidopsis thaliana with an inhibition degree of five. Compound 6d also showed an inhibition degree of five against D. sanguinalis. In addition, at 50?mg/L, most compounds exhibited good in vitro antifungal activity against Sclerotinia sclerotiorum, with compound 6c showing over 90% antifungal activity against S. sclerotiorum and Pellicularia sasakii.

Full text of DOI:10.1016/j.cclet.2016.06.019

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CCLET-3742; No. of Pages 4
Chinese Chemical Letters xxx (2016) xxx–xxx
Contents lists available at ScienceDirect
Chinese Chemical Letters
journal homepage: www.elsevier.com/locate/cclet
Original article
Synthesis and biological activity of novel N-(3-furan-2-yl-1-phenyl-
H-pyrazol-5-yl) amides derivatives
1
a
b
a
b,c,
a,
Jing-Qian Huo , Liu-Yong Ma , Zhe Zhang , Zhi-Jin Fan *, Jin-Lin Zhang *,
d
d
Tetyana V. Beryozkina , Vasiliy A. Bakulev
a
College of Plant Protection, Agricultural University of Hebei, Baoding 071001, China
b
c
State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China
Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071, China
The Ural Federal University Named after the First President of Russia B.N. Yeltsin, Ekaterinburg 620002, Russia
d
A R T I C L E I N F O
A B S T R A C T
Article history:
A series of novel N-(3-furan-2-yl-1-phenyl-1H-pyrazol-5-yl) amides derivatives were designed and
Received 23 May 2016
Received in revised form 2 June 2016
Accepted 7 June 2016
Available online xxx
1
13
synthesized. Their structures were confirmed by H NMR, C NMR and HRMS. All title compounds were
evaluated for their herbicidal and antifungal activities. Preliminary bioassay results indicated that the
title compounds showed good to moderate herbicidal activity at 1000 mg/L. Compound 6q presented the
best activity against Digitaria sanguinalis (L) Scop., Amaranthus retroflexus L. and Arabidopsis thaliana with
an inhibition degree of five. Compound 6d also showed an inhibition degree of five against D. sanguinalis.
In addition, at 50 mg/L, most compounds exhibited good in vitro antifungal activity against Sclerotinia
sclerotiorum, with compound 6c showing over 90% antifungal activity against S. sclerotiorum and
Pellicularia sasakii.
Keywords:
Amides derivative
Pyrazole
Furan
ß 2016 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.
Published by Elsevier B.V. All rights reserved.
Synthesis
Herbicidal activity
Fungicidal activity
1
. Introduction
Pesticides play an important role in agricultural development in
drug screening technology, an amide compound 12007063, with
good biological activity, which targeted transketolase was discov-
ered. Amide compounds are widely used as pesticides. For
example, propanil belongs to the photosystem PSII herbicides,
and fluopyram which belongs to SDHI (succinate dehydrogenase
inhibitors) fungicides is also an amide compound. In this study, a
series of N-(3-furan-2-yl-1-phenyl-1H-pyrazol-5-yl) amide deri-
vatives were designed and synthesized for biological screening
from lead compound 12007063 by introducing bioactive sub-
structures into the target molecules using the principle of pesticide
molecular designation (Fig. 1).
our country. However, pesticide resistance has become a serious
concern due to continuous application of a single pesticide with a
unique mode of action [1–5], Natural products, often having new
modes of action, low-residue and high selectivity, are important
pesticide leads [6], and following structure optimization, natural
products are strong candidates for the pesticide market [7,8].
Identifying new lead compounds is imperative for pesticide
development [9,10]. In recent years, the combination of computer
simulation, chemical synthesis and biological testing has become
the new policy for drug development in the post genomic era [11].
This has an important impact on novel pesticide development.
Transketolase is widely distributed among plants, animals,
fungi and bacteria [12], and plays an important role in the calvin
cycle of plant photosynthesis [13,14]. It has potential as a new
herbicide target [15]. In a previous study, using computer-aided
2. Experimental
2.1. Chemistry
Reagents and solvents were analytical grade and the anhydrous
reagents were dried by standard methods. The melting points were
measured on an XT-4A apparatus and uncorrected. NMR spectra
were obtained on a Bruker AV-400 spectrometer operating at
*
Corresponding authors.
1
13
4
00 MHz for H NMR and 100 MHz for C NMR. NMR resonances
E-mail addresses: fanzj@nankai.edu.cn (Z.-J. Fan), zhangjinlin@hebau.edu.cn
(J.-L. Zhang).
were registered using CDCl as solvents and TMS as the internal
3
http://dx.doi.org/10.1016/j.cclet.2016.06.019
1
001-8417/ß 2016 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
Please cite this article in press as: J.-Q. Huo, et al., Synthesis and biological activity of novel N-(3-furan-2-yl-1-phenyl-1H-pyrazol-5-yl)
amides derivatives, Chin. Chem. Lett. (2016), http://dx.doi.org/10.1016/j.cclet.2016.06.019

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3. Results and discussion
3.1. Synthesis
Heterocyclic compounds are important lead sources for drug
and pesticide development and the methods for their construction
are well reported [21–23]. Our former research discovered one
compound, containing furan and pyrazole ring, which could be
studied as an herbicide lead. This study focused on optimization of
this lead and a series of novel N-(3-furan-2-yl-1-phenyl-1H-
pyrazol-5-yl) amides derivatives from 3-(furan-2-yl)-1 -phenyl-H-
pyrazol-5-amine (3) was synthesized. We first tried to prepare 3-
(furan-2-yl)-1-phenyl-H-pyrazol-5-amine (3) using EtOH as the
solvent, and the cycling reaction of 2-furoylacetonitrile with
phenylhydrazine was progressed at the reflux temperature. By-
product was formed and the yield of the desired product was low.
However, after optimization of the reaction conditions, the yield
was increased from 54.01% to 90.09% [24]. 2-Furoylacetonitrile
was allowed to react with phenylhydrazine at 130 8C for 1 h, and
the desired 3-(furan-2-yl)-1-phenyl-H-pyrazol-5-amine (3) was
successfully generated with over 90% yield.
During the synthesis of the target compounds (6), intermediate
3 did not react completely, and the retention factor values of the
target compounds and intermediate 3 were very close. It was
difficult to separate and purify the target compounds using column
chromatography. After washing with HCl, the alkalic intermediate
was easily moved, and the purification efficiency of the target
compounds by chromatography was significantly improved. The
chemical structures of the target compounds were confirmed by
spectroscopic data, and these data are given in Supporting
Fig. 1. The structure of herbicide lead compound 12007063.
standard. The high resolution mass spectra were recorded on an
Agilent 6520-QTOF LC/MS having ESI source in positive mode.
Synthesis of the title compounds was conducted as shown in
Scheme 1. Methyl furan-2-carboxylate (compound 1) was
prepared according to literature [16]. Intermediate 2 was prepared
3
via the reaction of methyl furan-2-carboxylate with CH CN and
NaH in toluene by refluxing for 24 h [17]. The cyclization of
compound 2 with phenylhydrazine gave intermediate 3. Com-
pounds 5a–5t were obtained by the reaction of 4a–4t with SOCl
and a catalytic amount of DMF by refluxing. Compounds 6a–6t
were synthesized by way of a condensation reaction using Et N as
the base in CH Cl . The structures of all newly synthesized
2
3
2
2
1
13
compounds were characterized by melting points, H NMR,
NMR and HRMS.
C
2
.2. Biological assay
The herbicide activity of the target compounds was evaluated
through foliar treatment [18]. The symptoms were monitored at
8 h post-treatment and compared with the control group. The
4
grading standard [19] for the inhibition effect is shown in Table 1.
The target plants tested for herbicide efficacy were Digitaria
sanguinalis L., Echinochloa crusgalli L., Amaranthus retroflexus L.,
Portulaca oleracea L. and Arabidopsis thaliana.
The fungicide activity of the target compounds was tested using
the fungi growth inhibition method [20]. Representative fungi
used in this study included Alternaria solani (AS), Botrytis cinerea
information. Here, the spectroscopic data of 6t were given as a
1
representative. 6t: H NMR (400 MHz, CDCl
3
):
d
8.82 (s, 1H, NH),
7.49 (d, 3H, J = 7.2 Hz, Ph-H), 7.43 (dd, 3H, J = 15.7, 7.6 Hz, Ar-H),
7.09 (s, 1H, Pyrazole-H), 6.90 (d, 1H, J = 7.3 Hz, Ph-H), 6.79 (d, 1H,
J = 8.1 Hz, Ph-H), 6.77 (d, 1H, J = 3.5 Hz, Furan -H), 6.67 (d, 1H,
J = 8.0 Hz, Ph-H), 6.51 (d, 1H, J = 1.7 Hz, Furan-H), 4.73 (s, 2H, –
1
3
OCH
CDCl
2
–), 3.04 (s, 2H, CH
2
), 1.43 (s, 6H, 2Â CH
3
). C NMR (101 MHz,
(BC), Cercospora arachidicola(CA), Gibberella zeae (GZ), Phy-
3
): 165.77, 148.34, 147.67, 144.48, 142.22, 141.68, 137.51,
d
tophthora infestans (Mont) de Bary (PI), Physalospora piricola (PP),
Pellicularia sasakii (PS), Sclerotinia sclerotiorum (SS), and Rhizoctonia
cerealis (RC).
135.56, 129.80, 129.47, 128.38, 124.57, 120.73, 119.90, 114.59,
111.31, 106.75, 95.44, 88.16, 69.20, 43.07, 28.18. HRMS(ESI)
+
[M+H] calcd. for C25
H
23
N
3
O
4
: 430.1767, found: 430.1760.
o
(i) CH
3
CN (3.0 equiv.), NaH (3.0 equiv.), Toluene, reflux for 24 h; (ii) Phenylhydrazine (1.0 equiv.), 130 C for 1 h, yield 90.09%;
(iii) SOCl
2
(5.0 equiv.), DMF (a catalytic amount ), reflux for 5 h; (iv) Et
3
N (1.2 equiv.), CH
2
Cl, room temperature overnight.
Scheme 1. Synthesis of the target compounds.
Please cite this article in press as: J.-Q. Huo, et al., Synthesis and biological activity of novel N-(3-furan-2-yl-1-phenyl-1H-pyrazol-5-yl)
amides derivatives, Chin. Chem. Lett. (2016), http://dx.doi.org/10.1016/j.cclet.2016.06.019

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J.-Q. Huo et al. / Chinese Chemical Letters xxx (2016) xxx–xxx
3
Table 1
herbicidal activity of compound 6q against A. thaliana was slightly
better than that of lead compound 12007063. Compound 6n
showed better activity against broadleaf weeds.
Herbicidal activity of test compounds at 1000 mg/mL.
Compd.
Herbicidal activity (inhibition degree)
Digitaria Echinochloa Amaranthus Portulaca Arabidopsis
The herbicidal efficacy of the target compounds showed that
sanguinalis crusgalli
retroflexus
oleracea
thaliana
3
introducing F, Cl or CF into the phenyl ring could improve the
herbicidal activity. Further studies found that the herbicidal
activity and the weed controlling spectrum of compounds 6d and
6
6
6
6
6
6
6
6
6
6
6
6
6
6
6
6
6
6
6
6
1
a
1
1
1
5
1
2
1
3
3
2
4
2
2
2
3
4
5
1
2
2
5
1
2
1
4
2
1
2
3
2
2
3
2
2
2
2
3
4
2
1
1
4
1
1
1
4
2
2
1
2
3
3
3
2
2
4
1
3
5
1
1
1
5
1
1
1
3
1
1
2
3
3
2
3
2
2
4
1
3
4
1
1
2
4
0
0
1
4
2
1
1
2
3
2
4
2
3
4
1
3
5
0
1
1
4
b
c
6k could be significantly improved by the introduction of CF
to the ortho-positions of the benzene ring. By comparison,
introducing CF (6p) or a nicotinic acid group (6q) to the pyridine
3
or F
d
e
3
f
ring of compounds 6p–6s could increase their herbicidal activity
and expand their herbicide spectrum. Compounds 6d and 6q had
good herbicidal activity and a broad spectrum, and they deserve
further investigation. Compound 6n showed better activity against
broadleaf targets with good selectivity.
g
h
i
j
k
l
m
n
3.2.2. Fungicide activity of the target compounds
o
As summarized in Table 2, all of the target compounds showed
fungicide activity against the selected fungi in vitro at 50 mg/L. The
fungicide activity and the antifungal spectrum of the target
compounds were improved when compared with the compound
12007063. All compounds demonstrated moderate to good
antifungal activity against S. sclerotiorum with growth inhibition
over 60%. Notably, compounds 6f, 6o and 6q demonstrated 100%
growth inhibition of S. sclerotiorum. Against P. sasakii, compound
p
q
r
s
t
2007063
Note: 0: The rate of growth inhibition was same as control; 1: The rate of growth
inhibition was below 25%; 2: The rate of growth inhibition was between 25% and
5
0%; 3: The rate of growth inhibition was between 50% and 75%; 4: The rate of
6c presented the highest activity with an inhibition rate of 91%.
growth inhibition was between 75% and 95%; 5: The rate of growth inhibition was
over 95%.
Compounds 6b and 6t showed the best activity against the strain of
C. arachidicola with the inhibition rate of 54%. Compounds 6a and
6
g were the most active compounds toward the strain of P. piricola
attested by an inhibition rate over 80%. Compound 6a, 6b, 6c, 6g,
m and 6t presented the good activity against more than one fungi
3
3
.2. Biological evaluations
6
.2.1. Herbicidal activity of the target compounds.
with the inhibition rate was higher than 70%. So the EC50 of these
compounds against the corresponding fungi was tested and the
results were showed in Table 3.
Herbicidal activity of the target compounds was evaluated
using the foliar treatment method. The results indicated that
Table 1) all of the target compounds showed moderate to good
(
Comparison of the fungicidal activity of the target compounds
herbicidal activity against the target weeds at 1000 mg/L.
Compound 6d exhibited good herbicidal activity, and the degree
of inhibition against D. sanguinalis was 5 which was equal to that of
lead compound 12007063. Compound 6q also showed good
herbicidal activity against the target weeds, and the inhibition
degree against D. sanguinalis, A. retroflexus and A. thaliana was 5,
while, for E. crusgalli and P. oleracea, the results were 4 degree. The
3
illustrated that the introduction of F, Cl or CF into the benzene ring
could increase antifungal activity and expand the antifungal
spectrum. Further studies found that the antifungal activity and
3
spectrum were indeed improved by introducing F (6f) or CF (6c)
groups into the meta-position at the benzene ring. The antifungal
activity of compounds 6l and 6m showed that introduction of Cl
did not improve their fungicidal activity. The antifungal activity of
Table 2
Fungicidal activity of test compounds (50
mg/mL).
Compd. Antifungal activity (% inhibition)
P. infestans
C. arachidicola
A. solani
B. cinerea
G. zeae
P. piricola
S. sclerotiorum
R. cerealis
P. sasakii
6
6
6
6
6
6
6
6
6
6
6
6
6
6
6
6
6
6
6
6
1
a
14
27
23
23
32
18
18
30
22
43
17
35
30
18
18
22
14
18
9
8
54
23
31
38
38
12
36
45
27
27
36
27
31
46
27
38
8
24
47
41
24
44
41
35
41
41
45
41
36
36
29
41
50
24
35
29
47
30
10
80
30
30
60
60
0
4
33
30
33
19
56
11
43
48
38
19
38
33
37
41
62
22
48
19
30
16
81
0
96
94
96
92
96
100
96
67
71
71
64
71
76
92
100
79
100
96
92
85
63
17
26
30
9
0
17
91
20
22
52
24
28
28
36
24
24
24
4
b
c
38
0
d
e
25
63
88
19
14
43
0
0
f
4
g
9
h
60
45
55
50
60
70
20
50
65
20
20
60
70
24
18
14
36
14
18
18
9
i
j
k
l
0
m
0
n
25
25
57
38
0
o
26
9
59
24
43
39
43
11
13
p
q
17
4
r
s
23
54
17
25
13
10
4
t
18
27
17
36
2007063
Please cite this article in press as: J.-Q. Huo, et al., Synthesis and biological activity of novel N-(3-furan-2-yl-1-phenyl-1H-pyrazol-5-yl)
amides derivatives, Chin. Chem. Lett. (2016), http://dx.doi.org/10.1016/j.cclet.2016.06.019

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Table 3
The EC50 of the selected compounds.
Compd.
Fungi
Regression equation
r
EC50 (mg/L)
6
6
6
6
6
6
a
b
c
P. piricola
y = 2.214x + 2.301
y = 2.809x + 1.417
y = 2.021x + 2.596
y = 1.920 +2.624
y = 2.020x +2.688
y = 1.970x + 2.573
y = 2.044x + 2.335
y = 2.439x + 2.004
y = 1.818x + 2.249
y = 2.466x + 1.245
y = 1.702x + 2.438
y = 1.615x + 2.785
0.999
0.997
0.994
0.992
0.985
0.995
0.979
0.986
0.996
0.985
0.987
0.998
16.57
18.85
15.47
17.27
13.94
17.06
20.12
16.92
32.59
33.29
31.98
23.53
S. sclerotiorum
B. cinerea
S. sclerotiorum
P. sasakii
S. sclerotiorum
P. piricola
g
m
t
S. sclerotiorum
B. cinerea
S. sclerotiorum
B. cinerea
S. sclerotiorum
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Please cite this article in press as: J.-Q. Huo, et al., Synthesis and biological activity of novel N-(3-furan-2-yl-1-phenyl-1H-pyrazol-5-yl)
amides derivatives, Chin. Chem. Lett. (2016), http://dx.doi.org/10.1016/j.cclet.2016.06.019