Synthesis and biological activities of O-(E)-(arylmethyl) 1-[1-(arylmethyl)-5-methyl-1H-1,2,3-triazol-4-yl] ethanone oxime ethers

Article abstract of DOI:10.1002/jhet.209

(Chemical Equation Presented) A series of novel O-(E)-(arylmethyl) 1-[1-(arylmethyl)-5-methyl-1H-1,2,3-triazol-4-yl] ethanone oxime ethers were synthesized by the O-alkylation of 1-[1-(arylmethyl)-5-methyl-1H-1,2,3-triazol- 4-yl] ethanone oximes with various arylmethyl chlorides in the basic condition. Their structures were confirmed by IR, ¹H NMR, mass spectroscopy, and elemental analyses. The preliminary bioassay indicated that some of the target compounds (4a-f) displayed good insecticidal and moderate fungicidal activity. For example, compounds 4c and 4g showed 100% and 90.6% death rates against aphides at the concentration of 250 mg/L, respectively, and compounds 4f and 4g displayed 67% and 78.4% inhibitory rates against Rhizoctonia solani at the dosage of 100 mg/L, respectively.

Full text of DOI:10.1002/jhet.209

1218
Synthesis and Biological Activities of O-(E)-(Arylmethyl)
1-[1-(arylmethyl)-5-methyl-1H-1,2,3-triazol-4-yl]
Ethanone Oxime Ethers
Vol 46
Xiao-Fei Zhu and De-Qing Shi*
Key Laboratory of Pesticide and Chemical Biology of Ministry of Education,
College of Chemistry, Central China Normal University, Wuhan 430079, Hubei,
People’s Republic of China
*E-mail: chshidq@mail.ccnu.edu.cn
Received June 18, 2008
DOI 10.1002/jhet.209
Published online 5 November 2009 in Wiley InterScience (www.interscience.wiley.com).
A series of novel O-(E)-(arylmethyl) 1-[1-(arylmethyl)-5-methyl-1H-1,2,3-triazol-4-yl] ethanone
oxime ethers were synthesized by the O-alkylation of 1-[1-(arylmethyl)-5-methyl-1H-1,2,3-triazol-4-yl]
ethanone oximes with various arylmethyl chlorides in the basic condition. Their structures were con-
1
firmed by IR, H NMR, mass spectroscopy, and elemental analyses. The preliminary bioassay indicated
that some of the target compounds (4a–f) displayed good insecticidal and moderate fungicidal activity.
For example, compounds 4c and 4g showed 100% and 90.6% death rates against aphides at the concen-
tration of 250 mg/L, respectively, and compounds 4f and 4g displayed 67% and 78.4% inhibitory rates
against Rhizoctonia solani at the dosage of 100 mg/L, respectively.
J. Heterocyclic Chem., 46, 1218 (2009).
INTRODUCTION
biological and pharmacological activities, as well as low
toxicity toward mammals, and the widely development
of neonicotinic insecticides in the world are very suc-
cessful examples [14–17]. As a continuation of our
ongoing project aimed at investigating novel biologi-
cally nitrogen-containing heterocyclic compounds
[18,19], we designed and synthesized a series of novel
O-(E)-(arylmethyl) 1-[1-(arylmethyl)-5-methyl-1H-1,2,3-
triazol-4-yl] ethanone oxime ethers. We would like to
report the synthesis and biological activities of the title
compounds 4a–g in this article (Scheme 1).
Oxime ether derivatives are very important agrochem-
icals and are receiving more and more attention because
of their widespread biological activities—some of them
can be used as insecticides, acaricides [1,2], fungicides
[3,4], and herbicides and its safener [5,6]—which are
widely used in the worldwide plant protection. The
1,2,3-triazole ring has been known for more than
100 years. However, it was only in recent decades that
the 1,2,3-triazole chemistry developed very fast due to
the discovery of the diverse biologically active triazole
derivatives. Many of them have been used as insecti-
cides, nematocides, acaricides, and plant growth regula-
tors [7–13]. Recently, heterocyclic compounds contain-
ing nitrogen play more and more important role in pesti-
cide science and industry; moreover, the introduction of
a pyridyl or a thiazole ring into a parent compound may
improve its properties and biological activities in the
looking for novel pharmaceutical and agrochemical lead
compounds, and many pyridyl and thiazole containing
compounds are also known to possess a wide range of
RESULTS AND DISCUSSION
2-Chloro-5-(chloromethyl)-pyridine (or thiazole) was
treated with sodium azide in dry ethanol under refluxing
condition to obtain 5-(azidomethyl)-2-chloro-pyridine
(or thiazole) (1) in high yields, which was annulated
with acetylacetone in DMSO in the presence of anhy-
drous potassium carbonate to generate compound 2.
Treatment of
2 with hydroxylamine hydrochloride
C
V
2009 HeteroCorporation

November 2009
Synthesis and Biological Activities of O-(E)-(Arylmethyl)
1-[1-(arylmethyl)-5-methyl-1H-1,2,3-triazol-4-yl] Ethanone Oxime Ethers
1219
Scheme 1
of 250 mg/L according to a previously reported method
[21]. The results of preliminary bioassays indicated that
some of the target compounds displayed good insectici-
dal activity against aphides (Table 1). For example,
compounds 4c and 4g exhibited 100% and 90.6% inhibi-
tory rates against aphides at the concentration of 250
mg/L, respectively.
Fungicidal activity. The preliminary fungicidal activ-
ity of the target compounds 4 was evaluated by the clas-
sic plate method at a dosage of 100 mg/L, which was
described in the experimental part. The six fungi used—
Fusarium oxysporium, Rhizoctonia solani, Botrytis cin-
ereapers, Gibberella zeae, Dothiorella gregaria, and
Colletotrichum gossypi—belong to the group of field
fungi and were isolated from corresponding crops. The
activities data were also listed in Table 1. The results
indicated that most of compounds 4 exhibit moderate to
weak inhibitory activities against the above six fungi.
For example, compounds 4f and 4g displayed 67% and
78.4% inhibitory rates against Rhizoctonia solani at the
dosage of 100 mg/L, respectively. Further structure-ac-
tivity relationships are under investigation.
afforded oxime 3, which reacted with various arylmethyl
chlorides in the basic condition to get the title com-
pounds 4 in moderate yields.
To optimize the reaction condition of O-alkylation,
we attempted to react 1-[1-(arylmethyl)-5-methyl-1H-
1,2,3-triazol-4-yl]ethanone oxime 3 with various alkyl
chlorides in different base-solvent systems (e.g., Et3N-
CH2Cl2, Et3N-CH3CN, Et3N-toluene, NaOH-CH3CN,
NaOH-DMF, and NaOH-toluene). Finally, we found that
the O-alkylation can take place smoothly in sodium
hydroxide and acetonitrile system to give the target
products 4 in moderate yield (58–85%), and no other
by-product was detected by TLC. In the O-alkylation, 2-
chloro-5-(chloromethyl)-pyridine and 2-chloro-(5-chloro-
methyl)-thiazole are more active than 3-(chloromethyl)-
pyridine and benzyl chloride. For example, when 2-
chloro-5-(chloromethyl)-pyridine and 2-chloro-(5-chloro-
methyl)-thiazole are used as the alkylation reagents, the
reaction can complete at room temperature for 4 to 5 h,
however, for 3-(chloromethyl)-pyridine and benzyl chlo-
ride, the reactions underwent very slow and needed
more high temperature and prolonged reation time.
Their structures of compounds 4 were confirmed by
IR, 1H NMR, EI-MS, and elemental analyses, which
were listed in the experimental part. Because of C¼¼N
bond, it probably existed as Z and E-isomers in com-
In conclusion, a series of novel O-(E)-(arylmethyl) 1-
[1-(arylmethyl)-5-methyl-1H-1,2,3-triazol-4-yl] ethanone
oxime ethers were synthesized by the O-alkylation reac-
tions of 1-[1-(arylmethyl)-5-methyl-1H-1,2,3-triazol-4-
yl] ethanone oximes with various arylmethyl chlorides
in the basic condition. The preliminary bioassay indi-
cated that some of the target compounds (4a–f) dis-
played good insecticidal and moderate fungicidal activ-
ity. For example, compounds 4c and 4g showed 100%
and 90.6% death rates against aphides at the concentra-
tion of 250 mg/L, compounds 4f and 4g displayed 67%
and 78.4% inhibitory rates against Rhizoctonia solani at
the dosage of 100 mg/L, respectively.
EXPERIMENTAL
Melting points were determined with a WRS-1B digital
melting point apparatus and are uncorrected. 1H NMR
spectra was recorded with a Varian Mercury PLUS400 spec-
trometer with TMS as the internal reference and CDCl3 as
the solvent, while mass spectra were obtained with a Finni-
gan TRACEMS2000 spectrometer using the EI method. Infra-
red (IR) spectra were measured by a Nicolet NEXUS470
spectrometer. Elemental analyses were performed with an Ele-
mentar Vario ELIII CHNSO elemental analyzer. All the solvents
and materials were reagent grade and purified as required. 5-
(Azidomethyl)-2-chloro-pyridine (or thiazole) (1a–b) was pre-
pared according to the literature procedure [22].
General procedure for the synthesis of 1-[1-(arylmethyl)-
5-methyl-1H-1,2,3-triazol-4-yl] ethanone 2 [23]. 5-(Azido-
methyl)-2-chloro-pyridine (or thiazole) 1 (0.05 mol) and ace-
tylacetone (5.0 g, 0.05 mol) were added to a suspension of
milled potassium carbonate (20.7 g, 0.15 mol) in DMSO (50
mL). The mixture was stirred at room temperature for 6–8 h
1
pounds 3 and 4a–g. In H NMR spectra, the CH3 pro-
tons of the E isomer is shifted downfield relative to that
of Z isomer, owing to its shorter distance between the
oxygen atom in C¼¼NAOA moiety and stronger
unshielded effect [1]. In this article, both of compounds
3 and 4 are in E configurations, which were deduced by
NMR analysis and further by compared with one of its
phosphorothioate analog determined by X-ray diffraction
analysis [20].
Biological activity
Insecticidal activity. Compounds 4 were tested for in-
secticidal activities against aphides at the concentration
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

1220
X.-F. Zhu and D.-Q. Shi
Vol 46
Table 1
The insecticidal and fungicidal activities of 4a–4g (inhibitory rate (%).
Fungicidal activity (100 mg/L)
Insecticidal
activity (250 mg/L)
against aphides
Fusarium
oxysporium
Rhizoctonia
solani
Botrytis
cinereapers
Gibberella
zeae
Dothiorella
gregaria
Colletotrichum
gossypii
Compd.
4a
4b
4c
4d
4e
4f
50.9
45.8
100
23.1
30.4
34.6
26.9
23.1
15.4
26.9
44.3
52.5
63.9
52.6
38.1
67.0
78.4
22.2
33.3
40.7
25.9
55.6
48.2
51.9
61.1
54.6
58.3
55.6
50.0
38.9
63.9
65.4
52.4
50.0
53.9
30.8
15.4
69.2
66.7
45.5
48.2
55.7
48.2
29.6
51.9
23.3
16.0
44.8
90.6
4g
(monitored by TLC); the mixture was poured to water (500
mL). The solid was collected by filtration, washed with water
and diethyl ether, and dried to give 2 as a white solid.
tered off, and the filtrate was concentrated under vacuum. The
residue was purified by column chromatography on silica gel
using petroleum ether and ethyl acetate (1:1 v/v) as the eluent,
giving the corresponding 4a–g in 58–85% yields.
O-(E)-[(6-chloropyridin-3-yl)methy] 1-{1-[(6-chloropyridin-
3-yl)methyl]-5-methyl-1H-1,2,3-triazol-4-yl} ethanone oxime
ether (4a). White crystal, yield: 85%, mp 125–127ꢀC; IR:
C¼¼N 1589, 1566, Ar 1460, 1436, 1388, 1349, N-O-C 1019;
1H NMR (CDCl3): d 2.31 (s, 3H, CH3), 2.40 (s, 3H, CH3),
5.13 (s, 2H, CH2), 5.47 (s, 2H, CH2), 7.27–8.40 (m, 6H, PyH);
ms: m/z 388 (Mþ, 94.1), 264 (9.2), 248(4.50), 126 (100). Anal.
Calcd. for C17H16Cl2N6O: C, 52.19; H, 4.12; N, 21.48. Found:
C, 52.33; H, 4.34; N, 21.32.
1-{1-[(6-Chloropyridin-3-yl) methyl]-5-methyl-1H-1,2,3-tria-
zol-4-yl} ethanone (2a) [19]. White solid, yield: 81%, mp
121–122ꢀC; 1H NMR (CDCl3): d 2.55 (s, 3H, CH3), 2.69 (s,
3H, CH3), 5.52 (s, 2H, CH2), 7.36 (d, J ¼ 8.4 Hz, 1H, PyH),
7.52 (d, J ¼ 11.2 Hz, 1H, PyH), 8.36 (s, 1H, PyH).
1-{1-[(2-Chlorothiazol-5-yl) methyl]-5-methyl-1H-1,2,3-tria-
zol-4-yl} ethanone (2b). White solid, yield: 78%, mp 97–
98ꢀC; 1H NMR (CDCl3): d 2.42 (s, 3H, CH3), 2.48 (s, 3H,
CH3), 5.60 (s, 2H, CH2), 7.51 (s, 1H, thiazole-H).
General procedure for the synthesis of 1-[1-(arylmethyl)-
5-methyl-1H-1,2,3-triazol-4-yl] ethanone oxime (3a–b). To
the stirred mixture of hydroxylamine hydrochloride (2.2 g, 32
mmol), 2 (20.0 mmol), ethanol (40 mL), and H2O (4 mL), so-
dium hydroxide (2 g, 50 mmol) was added slowly. After the
addition completed, the solution was stirred at room temperature
(for 3b) or under reflux (for 3a) for 5–6 h, the mixture was
poured to water (200 mL). The solid was collected by filtration
and recrystallized from toluene to get 3 as a white solid.
O-(E)-[(2-chlorothiazol-5-yl)methyl] 1-{1-[(6-chloropyridin-
3-yl)methyl]-5-methyl-1H-1,2,3-triazol-4-yl}ethanone
oxime
ether (4b). White crystal, yield: 82%, mp 90–91ꢀC; IR: C¼¼N
1590, 1566, Ar 1461, 1412, 1396, 1366, N-O-C 1017; 1H
NMR (CDCl3): d 2.40 (s, 3H, CH3), 2.41 (s, 3H, CH3), 5.22
(s, 2H, CH2), 5.50 (s, 2H, CH2), 7.26–8.35 (m, 4H, thiazole-H,
PyH); ms: m/z 396 (Mþ, 12.5), 131 (100), 126 (94.3), 89
(47.7), 70 (69.4). Anal. Calcd. for C15H14Cl2N6OS: C, 45.35;
H, 3.55; N, 21.15. Found: C, 45.03; H, 3.62; N, 20.97.
O-(E)-benzyl 1-{1-[(6-chloropyridin-3-yl)methyl]-5-methyl-
1H-1,2,3-triazol-4-yl}ethanone oxime ether (4c). White crys-
tal, yield: 80%, mp 75–77ꢀC; 1H NMR (CDCl3): d 2.31 (s,
3H, CH3), 2.41 (s, 3H, CH3), 5.16 (s, 2H, CH2), 5.47 (s, 2H,
CH2), 7.26–8.33 (m, 8H, PhH, PyH); Anal. Calcd. for
C18H18ClN5O: C, 60.76; H, 5.10; N, 19.68. Found: C, 60.85;
H, 5.23; N, 19.84.
1-{1-[(6-Chloropyridin-3-yl) methyl]-5-methyl-1H-1,2,3-tria-
zol-4-yl} ethanone oxime (3a). White solid, yield: 51%, mp
172–174ꢀC; IR: OH 3421, CH3 1419, 1385 cmꢁ1 1H NMR
;
(CDCl3): d 1.54 (s, 1H, OH), 2.42 (s, 3H, CH3), 2.43 (s, 3H,
CH3), 5.49 (s, 2H, CH2), 7.34 (d, J ¼ 8.0 Hz, 1H, PyH), 7.50
(d, J ¼ 10.8 Hz, 1H, PyH), 8.35 (s, 1H, PyH); ms: m/z 265
(Mþ, 10.5), 236 (37.1), 126 (100), 90 (22.3), 77 (8.3), 73
(32.9), 63 (15.8). Anal. Calcd. for C11H12ClN5O: C, 49.72; H,
4.55; N, 26.36. Found: C, 49.57; H, 4.75; N, 26.18.
1-{1-[(2-Chlorothiazol-5-yl) methyl]-5-methyl-1H-1,2,3-tria-
zol-4-yl} ethanone oxime (3b). White solid, yield: 43%, mp
139–141ꢀC; 1H NMR (CDCl3): d 1.62 (s, 1H, OH), 2.60 (s,
3H, CH3), 2.69 (s, 3H, CH3), 5.62 (s, 2H, CH2), 7.53 (s, 1H,
thiazole-H). Anal. Calcd. for C9H10ClN5OS: C, 39.78; H, 3.71;
N, 25.77. Found: C, 39.94; H, 3.53; N, 25.89.
O-(E)-[(pyridin-3-yl)methyl] 1-{1-[(6-chloropyridin-3-yl)methyl]
-5-methyl-1H-1,2,3-triazol-4-yl}ethanone oxime ether (4d). White
crystal, yield: 68%, mp 80–82ꢀC; IR: CH¼¼N 1586, Ar-H, Py-
H 1565, 1484, 1460, 1392, 1334, N-O-C 1033; 1H NMR
(CDCl3): d 2.39 (s, 3H, CH3), 2.41 (s, 3H, CH3), 5.18 (s, 2H,
CH2), 5.47 (s, 2H, CH2), 7.26–8.62 (m, 7H, PyH); Anal.
Calcd. for C17H17ClN6O: C, 57.22; H, 4.80; N, 23.55. Found:
C, 57.48; H, 4.74; N, 23.27.
General procedure for the synthesis of O-(E)-(arylmethyl)
1-[1-(arylmethyl)-5-methyl-1H-1,2,3-triazol-4-yl]
ethanone
O-(E)-[(6-chloropyridin-3-yl)methyl] 1-{1-[(2-chlorothiazol-
5-yl)methyl]-5-methyl-1H-1,2,3-triazol-4-yl}ethanone
oxime ethers 4a–g. A solution of 3 (2 mmol) in anhydrous
CH3CN (10 mL) and NaOH powder (2 mmol) was added to a
three-necked flask. After vigorously stirring for 5–10 min, a
solution of arylmethyl chloride (2 mmol) in anhydrous CH3CN
(5 mL) was added dropwise. After the addition completed, the
mixture was stirred at room temperature or under reflux till the
reaction was complete (monitored by TLC). The solid was fil-
oxime
ether (4e). Yellow oil, yield: 61%; IR: CH¼¼N 1592, Ar-H,
Py-H 1567, 1491, 1448, 1392, 1327, N-O-C 1039; 1H NMR
(CDCl3): d 2.60 (s, 3H, CH3), 2.60 (s, 3H, CH3), 5.14 (s, 2H,
CH2), 5.58 (s, 2H, CH2), 7.27–8.40 (m, 4H, thiazole-H, PyH).
Anal. Calcd. for C15H14Cl2N6OS: C, 45.35; H, 3.55; N, 21.15.
Found: C, 45.46; H, 3.78; N, 21.36.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

November 2009
Synthesis and Biological Activities of O-(E)-(Arylmethyl)
1-[1-(arylmethyl)-5-methyl-1H-1,2,3-triazol-4-yl] Ethanone Oxime Ethers
1221
[2] Zhang, L.; Li, Z.; Li, Z. Unsaturated oxime ethers and their
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O-(E)-[(2-chlorothiazol-5-yl)methyl] 1-{1-[(2-chlorothiazol-
5-yl)methyl]-5-methyl-1H-1,2,3-triazol-4-yl}ethanone
oxime
ether (4f). Yellow oil, yield: 74%; 1H NMR (CDCl3): d 2.38
(s, 3H, CH3), 2.60 (s, 3H, CH3), 5.22 (s, 2H, CH2), 5.61 (s,
2H, CH2), 7.49 (s, 1H, thiazloe-H), 7.52 (s, 1H, thiazole-H).
Anal. Calcd. for C13H12Cl2N6OS2: C, 38.71; H, 3.00; N,
20.84. Found: C, 38.96; H, 3.21; N, 20.93.
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O-(E)-benzyl 1-{1-[(2-chlorothiazol-5-yl)methyl]-5-methyl-
1H-1,2,3-triazol-4-yl}ethanone oxime ether (4g). Yellow oil,
yield: 58%; 1H NMR (CDCl3): d 2.36 (s, 3H, CH3), 2.40 (s,
3H, CH3), 5.17 (s, 2H, CH2), 5.57 (s, 2H, CH2), 7.27–7.52 (m,
6H, thiazole-H, PhH); ms: m/z 361 (Mþ, 10.9), 131 (34.8), 90
(100), 76 (60.7), 62 (25.7). Anal. Calcd. for C16H16ClN5OS:
C, 53.11; H, 4.46; N, 19.35. Found: C, 53.28; H, 4.70; N,
19.61.
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Fungicidal activity testing. The fungicidal activity mea-
surement method was adapted from the one described by
Molina-Torres et al. [24]. The synthesized target compounds
were dissolved in 0.5–1.0 mL of DMF to the concentration of
1000 mg/L. The solutions (1 mL) were mixed rapidly with
thawed potato glucose agar culture medium (9 mL) under
50ꢀC. The mixtures were poured into petridishes. After the
dished were cooled, the solidified plates were incubated with
4-mm mycelium disk, inverted, and incubated at 28ꢀC for
48 h. Distilled water was used as the blank control. Three rep-
licates of each test were carried out. The mycelial elongation
radius (mm) of fungi settlements was measured after 48 h of
culture. The growth inhibitory rates were calculated with the
following equation: I ¼ [(CꢁT)/C] ꢂ 100%. Here, I is the
growth inhibitory rate (%), T is the treatment group fungi set-
tlement radius (mm), and C is the radius of the blank control.
The results are listed in Table 1.
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Acknowledgments. This work was supported by the Natural
Science Foundation of China (Grant No. 20302002) and the Sci-
entific Research Foundation for the Returned Overseas Chinese
Scholars, Ministry of Education of China (Grant No.[2007]
1108).
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Journal of Heterocyclic Chemistry
DOI 10.1002/jhet