Synthesis and herbicidal activity of 2-aroxy-propanamides containing pyrimidine and 1,3,4-thiadiazole rings

Article abstract of DOI:10.1002/jhet.1853

A series of novel N-{5-[2-(4,6-dimethoxy-pyrimidin-2-yloxy)-phenyl]-[1,3,4] thiadiazol-2-yl}2-aroxy-propanamides were designed and synthesized by the multistep reactions. 2-(4,6-Dimethoxy-pyrimidin-2-yloxy)-benzaldehyde (1) reacted with aminothiourea to y

Full text of DOI:10.1002/jhet.1853

432
Synthesis and Herbicidal Activity of 2-Aroxy-propanamides Containing
Pyrimidine and 1,3,4-Thiadiazole Rings
Vol 51
*
Man-Yun Liu 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 August 2, 2012
DOI 10.1002/jhet.1853
Published online 18 November 2013 in Wiley Online Library (wileyonlinelibrary.com).
H3CO
S
H3CO
H3CO
N
N
N
S
N
N
S
N
N
N
FeCl3.6H2O
C2H5OH
NH2
NH2CNHNH2
O
CHO
C2H5OH, Reflux
H3CO
O
O
CH=NNHCNH 2
H3CO
H3CO
1
2
3
O
H3CO
H3CO
N
S
N
N
N
NHCCHOAr
CH3
O
ArOCHCOCl
CH3
3
+
Et3N/CH2Cl2
4a~4i
A series of novel N-{5-[2-(4,6-dimethoxy-pyrimidin-2-yloxy)-phenyl]-[1,3,4]thiadiazol-2-yl}2-aroxy-
propanamides were designed and synthesized by the multistep reactions. 2-(4,6-Dimethoxy-pyrimidin-2-
yloxy)-benzaldehyde (1) reacted with aminothiourea to yield 2, which undergoes ring closure to give
5-[2-(4,6-dimethoxy-pyrimidin-2-yloxy)-phenyl]-[1,3,4]thiadiazol-2-amine (3) in the presence of ferric
chloride in refluxing ethanol. 3 reacted with 2-aroxy-propionyl chlorides to give the target compounds
1
4a–4i in moderate to good yields. Their structures were confirmed by IR, H-NMR, EIMS, and elemental
analyses. The preliminary bioassay indicated that some of them displayed moderate to good selective
herbicidal activity against Brassica campestris L. at the concentration of 100 mg/L. However, these compounds
did not possess inhibitory activity against Echinochloa crus-galli at the tested concentrations.
J. Heterocyclic Chem., 51, 432 (2014).
INTRODUCTION
crus-galli (in vitro) were evaluated in this study. Herein, we
would like to report the synthesis and herbicidal activities of
the title compounds 4a–4i in this article (Scheme 1).
Recently, pyrimidinyl salicylic acid derivatives, which
acted as inhibitors of branched chain amino acids (acetolactate
synthase (ALS) or acetohydroxyacid synthase (AHAS))
synthase, have been found to be effective herbicides against
barnyard grass in different growth stages including pre-
emergence treatment and excellent safety on transplanted rice
crops, animals, fish, and so forth [1–5]. To date, several
pyrimidyl carboxylic acid derivatives such as bispyribac-
sodium and pyriminobac-methyl, have been used as
commercially herbicides (Figure 1), which are widely used
in agriculture and plant protection around the world. On the
other hand, 1,3,4-thiadiazole derivatives possessed a wide
range of pharmaceutical or agrochemical activities, such as
anticancer [6], antiviral [7], antibacterial [8], antimicrobial,
and anti-inflammatory activities [9]; some of them exhibited
good fungicidal [10] and herbicidal activities [11]. To find
novel lead compound with good herbicidal activity, we
designed and synthesized a series of novel N-{5-[2-(4,6-
dimethoxy-pyrimidin-2-yloxy)-phenyl]-[1,3,4]thiadiazol-2-yl}
2-aroxy-propanamides, according to the pesticide metabolism,
which might be hydrolyzed to 2-(4,6-dimethoxy-pyrimidin-2-
yloxy)-benzoic acid and 2-aroxy propionic acid in plant
tissues; both of them are effective herbicides. Their herbicidal
activities against Brassica campestris L. and Echinochloa
RESULTS AND DISCUSSION
4,6-Dimethoxypyrimidin-2-yl-methylsulfone reacted with
salicyl aldehyde in the presence of potassium carbonate to
give 2-(4,6-dimethoxypyrimidin-2-yloxy)benzaldehyde (1)
in 94% yield. 1 reacted with aminothiourea to form semicar-
bazone (2), which undergoes annulation in the presence
of FeCl3 to give 5-amino-2-[2-(4,6-dimethoxypyrimidin-2-
yloxy)-phenyl]-[1,3,4]thiadiazole (3) in moderate yield.
The target compounds 4 were synthesized by the condensa-
tions of 3 with 2-aroxy-propionyl chlorides in the presence
of Et3N at RT in moderate to good yields.
The structures of all of the target compounds were charac-
terized by H-NMR, IR spectra, and elemental analyses;
some of them were determined by EIMS spectrum, which
were listed in the Experimental Section. In the H-NMR
spectra of 4, the methyl protons exhibited as a doublet at
approximately 1.70, whereas the methine proton displayed
as a quartet at approximately 5.0. The two methoxy groups
of the pyrimidine ring and the pyrimidine proton also
showed as a singlet with the chemical shift at approximately
1
1
© 2013 HeteroCorporation

March 2014
Synthesis and Herbicidal Activity of 2-Aroxy-propanamides Containing Pyrimidine and
1,3,4-Thiadiazole Rings
433
H3CO
OCH3
H3C
NOCH3
COOCH3
N
N
H3CO
H3CO
OCH3
OCH3
O
COONa
O
N
N
N
N
OCH3
N
N
H
N
O
O
CO2Pr-n
OCH3
Pyriminobac-methyl
Bispyribac-sodium
ZJ 0273
Figure 1. Structures of some commercial pyrimidinyl carboxylic acid and pyrimidinyl benzylamine herbicides.
Scheme 1. Synthetic route to compounds 4a–4i.
H3CO
S
H3CO
H3CO
FeCl3.6H2O
N
N
N
S
N
N
N
N
S
N
NH2
NH2CNHNH2
O
CHO
C2H5OH, Reflux
H3CO
O
O
CH=NNHCNH2
C2H5OH
H3CO
H3CO
1
2
3
O
N
H3CO
N
N
N
NHCCHOAr
O
ArOCHCOCl
CH3
3
+
CH3
S
Et3N/CH2Cl2
H3CO
4a-4i
results were listed in Table 1. The results showed that these
compounds exhibited moderate selective herbicidal activity
against B. campestris L. at the concentration of 100 mg/L.
However, these compounds displayed weak inhibitory
activity against E. crus-galli at different concentration. For
example, compounds 4a, 4b, 4f, and 4i possessed 75.0%,
65.4%, 64.2%, and 87.6% inhibitory activities against B.
campestris L. at the concentration of 100 mg/L. As for the
preliminary structure-activity relationships, the substituents
of the benzene ring have some effects on their herbicidal
activity. For example, 2,4-dichloro substituted compound
(4i) exhibits the strongest activity, which shows as good
herbicidal activity as the control drug—bispyribac-sodium—
did. Secondly, varying substituents of the aromatic ring at
the different position have some effects on the herbicidal
activity. For example, 4-fluoro substituted one (4f) shows
better activity than 3-fluoro one (4c). However, as for
electron-donating substituents, 3-methyl substituted one
displays stronger activity than 4-methyl substituted one (4g).
Further exploring of structure-activity relationships needs
more experimental results to support. Further biological
activity (in vivo) investigations are on the way.
Table 1
Herbicidal activity of compounds 4a–4i (growth inhibition rate %).
Brassica campestris root
Echinochloa crus-galli cup
test
test
Compd.
10 mg/mL
100 mg/mL
10 mg/mL
100 mg/mL
4a
4b
4c
4d
4e
4f
4g
4h
4i
46.4
20.3
0
31.8
0
24.0
6.2
0
75.0
65.4
27.6
59.8
33.0
64.2
42.4
0
0
0
0
0
0
0
0
0
0
0
0
20.0
5.0
0
20.0
15.0
0
61.0
87.6
69.8
0
72.4
Bispyribac- 65.6
sodium
46.9
3.8 and 5.8, respectively; however, the amino proton
displayed a wide singlet with the chemical shift d at the range
of 10 and 11.5. The IR spectra of 4 revealed NH at
3450 cmÀ1, whereas the signal of 1700 cmÀ1 is attributed to
C=O absorption, and 1350 and 1220 cmÀ1 can be attributed
to C—O—C absorption bands. The mass spectra of the target
compounds 4 shows moderate molecular ion peak and
anticipated fragmentation ion peaks.
Herbicidal activity. The preliminary herbicidal activities
of compounds 4 were evaluated, against two representative
targets, oil rape and barnyard grass, at concentrations of
100 and 10 mg/L, according to a literature method [12]. The
In conclusion, a series of novel N-{5-[2-(4,6-dimethoxy-
pyrimidin-2-yloxy)-phenyl]-[1,3,4]thiadiazol-2-yl}2-aroxy-
propanamides (4) were designed and synthesized by the
multistep reactions. Their structures were determined by IR,
1H-NMR, EIMS, and elemental analyses. The preliminary
bioassay indicated that some of them displayed moderate
selective herbicidal activity against B. campestris L at the
concentration of 100 mg/L.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

434
M.-Y. Liu and D.-Q. Shi
Vol 51
Compound 4b. 4b (Ar=2-BrC6H4): white solid, yield: 62%,
mp 182–183ꢀC; 1H-NMR (CDCl3, 400 MHz) d: 1.74 (d,
J = 6.8Hz, 3H, CH3), 3.83 (s, 6H, 2 Â OCH3), 5.00 (q, J = 6.8 Hz,
1H, CH), 5.80 (s, 1H, pyrimidine-H), 6.95 (t, J = 7.2 Hz, 2H), 7.31
(t, J = 8.0 Hz, 2H), 7.35 (t, J = 7.6 Hz, 1H), 7.50 (t, J = 8.0 Hz,
1H), 7.60 (d, J = 8.0 Hz, 1H), 8.39 (d, J = 7.6 Hz, 1H), 10.35 (br,
1H, NH); IR (KBr) n: 3436 (NH), 2931 (ArH), 1697 (C=O),
1603, 1560, 1512 (Ar), 1355, 1196 (C—O—C) cmÀ1. Anal.
Calcd for C23H20BrN5O5S: C, 49.47; H, 3.61; N, 12.54. Found:
C, 49.61; H, 3.83; N, 12.67.
Compound 4c. 4c (Ar=3-FC6H4): white solid, yield: 75%, mp
176–177ꢀC; 1H-NMR (CDCl3, 400MHz) d: 1.70 (d, J =6.4Hz, 3H,
CH3), 3.84 (s, 6H, 2 Â OCH3), 5.01 (q, J= 6.4 Hz, 1H, CH), 5.81
(s, 1H, pyrimidine-H), 6.68–6.75 (m, 3H), 722–7.38 (m, 3H), 7.50
(t, J= 8.4 Hz, 1H), 8.36 (d, J = 8.4 Hz, 1H), 10.64 (br, 1H, NH); IR
(KBr) n: 3452 (NH), 2959 (ArH), 1686 (C=O), 1612, 1571, 1488
(Ar), 1362, 1210, 1192 (C—O—C) cmÀ1. Anal. Calcd for
C23H20FN5O5S: C, 55.53; H, 4.05; N, 14.08. Found: C, 55.39; H,
4.16; N, 13.92.
Compound 4d. 4d (Ar=3-CH3C6H4): white solid, yield: 74%,
mp 162–163ꢀC; 1H-NMR (CDCl3, 400MHz) d: 1.67 (d, J = 6.8 Hz,
3H, CH3), 2.30 (s, 3H), 3.83 (s, 6H, 2 Â OCH3), 5.02 (q, J = 6.4 Hz,
1H, CH), 5.81 (s, 1H, pyrimidine-H), 6.75 (t, J = 6.8 Hz, 2H), 6.83
(d, J = 7.6 Hz, 1H), 7.17 (d, J = 8.0 Hz, 1H), 7.31 (d, J = 8.0 Hz,
1H), 7.36 (d, J = 7.6 Hz, 1H), 7.50 (t, J = 7.6 Hz, 1H), 8.36 (d,
J = 8.0Hz, 1H), 10.70 (br, 1H, NH); IR (KBr) n: 3464 (NH),
2936 (ArH), 1715 (C=O), 1605, 1561, 1506 (Ar), 1342, 1225
(C—O—C) cmÀ1; EIMS (70eV): m/z 493.5 (M+, 29.6), 478
(5.8), 358 (30.4), 299 (9.9), 258 (22.3), 195 (12.8), 139 (12.6),
136 (12.0), 135 (51.1), 119 (13.1), 116 (14.5), 108 (21.3), 107
(22.8), 91 (100). Anal. Calcd for C24H23N5O5S: C, 58.41; H,
4.70; N, 14.19. Found: C, 58.56; H, 4.52; N, 14.33.
Compound 4e. 4e (Ar=4-ClC6H4): white solid, yield: 65%,
mp 174–175ꢀC; 1H-NMR (CDCl3, 400 MHz) d: 1.70 (d,
J = 6.8Hz, 3H, CH3), 3.83 (s, 6H, 2 Â OCH3), 5.08 (q, J = 6.8 Hz,
1H, CH), 5.81 (s, 1H, pyrimidine-H), 6.90 (d, J = 7.6 Hz, 2H),
7.23 (d, J = 7.6 Hz, 2H), 7.35 (t, J = 8.0 Hz, 2H), 7.49 (d,
J = 7.6Hz, 1H), 8.30 (d, J = 8.0 Hz, 1H), 11.46 (br, 1H, NH); IR
(KBr) n: 3458 (NH), 2940 (ArH), 1712 (C=O), 1608, 1565, 1502
(Ar), 1341, 1227 (C—O—C) cmÀ1; EIMS (70 eV): m/z 513 (M+,
40.0), 498 (13.8), 482 (29.9), 358 (48.9), 258 (76.5), 195 (40.7),
157 (42.4), 155 (76.9), 139 (48.0), 130 (22.6), 128 (40.9), 127
(44.9), 116 (30.3), 113 (36.3), 111 (100), 91 (69.5), 69 (33.6).
Anal. Calcd for C23H20ClN5O5S: C, 53.75; H, 3.92; N, 13.63.
Found: C, 53.70; H, 3.84; N, 13.88.
EXPERIMENTAL
Melting points were determined with a WRS-1B digital melting
point apparatus (Shanghai, China) and are uncorrected. H-NMR
1
spectra was recorded with a Varian Mercury PLUS 400
(400MHz) or PLUS 600 (600 MHz) spectrometer (Palo Alto, CA)
with TMS as the internal reference and CDCl3 or DMSO-d6 as
the solvent, whereas mass spectra were measured on a Finnigan
Trace MS 2000 spectrometer (Finnigan Cooperation, CA) at
70eV using EI method. IR spectra were measured by a Nicolet
NEXUS470 spectrometer (ThermoNicolet Corporation, USA). El-
emental analyses were performed with an Elementar Vario ELШ
CHNSO elemental analyzer (Elementar Cooperation, Germany).
2-(4,6-Dimethoxy-pyrimidin-2-yloxy)-benzaldehyde (1) and 2-
aroxy-propionyl chlorides can be prepared according to a reported
method [13,14], respectively. All of the solvents and materials
were reagent grade and purified as required.
Synthesis of 5-amino-2-[2-(4,6-dimethoxypyrimidin-2-yloxy)-
phenyl]-[1,3,4]thiadiazole (3) [11c]. 2-(4,6-Dimethoxy-pyrimidin-
2-yloxy)-benzaldehyde (1) (5 g, 19 mmol), aminothiourea (1.75 g,
19 mmol), and anhydrous ethanol (70 mL) were added to a 100-mL
three-necked flask; the mixture was allowed to be stirred at RT for
0.5 h and then was stirred under reflux for 4 h. After the mixture was
cooled to RT, the white solid was filtered and washed with ethanol
(5mL) to give 2 as white solid (6 g, 94% yield). mp 184–185ꢀC.
2 (4.25g, 12mmol), FeCl3.6H2O (12 g, 44 mmol), and anhydrous
methanol (45 mL) were added to a 100-mL three-necked flask; the
mixture were allowed to be stirred under reflux for 8 h. After most
of ethanol was removed under vacuum, water (100–150 mL) was
added; the solid was filtered and washed with water (50 mL Â 3);
3 was obtained as gray brown solid (3.5 g, 88% yield). mp
1
161–162ꢀC; H-NMR (DMSO-d6, 400 MHz) d: 3.76 (s, 6H), 5.41
(br, 2H), 5.78 (s, 1H), 7.22 (d, J= 7.8 Hz, 1H, ArH), 7.30
(t, J= 8.4 Hz, 1H, ArH), 7.41 (t, J= 7.2 Hz, 1H, ArH), 7.78
(d, J= 7.2 Hz, 1H, ArH). Anal. Calcd for C14H13N5O3S: C, 50.75;
H, 3.95; N, 21.14. Found: C, 50.87; H, 3.99; N, 21.01.
General procedure for the synthesis of N-{5-[2-(4,6-
dimethoxy-pyrimidin-2-yloxy)-phenyl]-[1,3,4]thiadiazol-2-yl}
2-aroxy-propanamides (4). 3 (1.66g, 5mmol), Et3N (0.5 mL), and
anhydrous CH2Cl2 (10 mL) were added to a 50-mL three-necked
flask, the solution of 2-aroxy-propionyl chloride (5 mmol) in
CH2Cl2 (2 mL) was added dropwise slowly in an ice bath. After the
addition completed, the mixture was allowed to be stirred at RT for
3–4 h till the reaction finished (monitored by TLC). After the
removal of the solvent followed by column chromatography of
the crude product on silica gel using a mixture of petroleum ether
(60–90ꢀC) and ethyl acetate (v/v, 2:1) as the eluent, compounds 4
were obtained as white or light yellow solids in 62–75% yields.
Compound 4a. 4a (Ar=C6H5): white solid, yield: 71%, mp
Compound 4f. 4f (Ar=4-FC6H4): white solid, yield: 68%, mp
1
168–170ꢀC; H-NMR (CDCl3, 400MHz) d: 1.67 (d, J = 6.8 Hz,
3H, CH3), 3.84 (s, 6H, 2 Â OCH3), 4.96 (q, J = 7.2 Hz, 1H, CH),
5.81 (s, 1H, pyrimidine-H), 6.91 (dd, J = 4.4 Hz, J = 9.2 Hz, 2H),
7.00 (t, J = 8.0 Hz, 2H), 7.32 (d, J = 8.0 Hz, 1H), 7.35 (d,
J = 7.6Hz, 1H), 7.51 (t, J = 8.0 Hz, 1H), 8.36 (d, J = 7.2Hz, 1H),
10.61 (br, 1H, NH); IR (KBr) n: 3468 (NH), 2921 (ArH), 1707
1
170–171ꢀC; H-NMR (CDCl3, 400 MHz) d: 1.68 (d, J = 6.8 Hz,
3H, CH3), 3.83 (s, 6H, 2 Â OCH3), 5.01 (q, J = 6.8 Hz, 1H,
CH), 5.80 (s, 1H, pyrimidine-H), 6.95 (d, J = 8.0 Hz, 2H), 7.03
(t, J = 7.2 Hz, 1H), 7.28–7.37 (m, 4H), 7.49 (t, J = 7.2 Hz, 1H),
8.36 (d, J = 7.6 Hz, 1H), 10.48 (br, 1H, NH); IR (KBr) n: 3441
(NH), 2935 (ArH), 1718 (C=O), 1608, 1565, 1510 (Ar), 1358,
1220 (C—O—C) cmÀ1; EIMS (70 eV): m/z 479.5 (M+, 27.6),
464.5 (10.7), 358 (27.0), 331 (11.6), 299 (9.8), 258 (15.5), 195
(15.9), 139 (13.1), 136 (11.3), 121 (57.6), 116 (15.9), 108
(14.6), 94 (15.9), 93 (24.4), 77 (100). Anal. Calcd for
C23H21N5O5S: C, 57.61; H, 4.41; N, 14.61. Found: C, 57.42; H,
4.46; N, 14.75.
(C=O), 1612, 1559, 1506 (Ar), 1345, 1218 (C—O—C) cmÀ1
.
Anal. Calcd for C23H20FN5O5S: C, 55.53; H, 4.05; N, 14.08.
Found: C, 55.30; H, 4.16; N, 14.29.
Compound 4g.
4g (Ar=4-CH3C6H4): white solid, yield:
1
70%, mp 172–173ꢀC; H-NMR (CDCl3, 400 MHz) d: 1.64 (d,
J = 6.8 Hz, 3H, CH3), 2.29 (s, 3H, CH3), 3.83 (s, 6H,
2 Â OCH3), 4.92 (q, J = 7.2 Hz, 1H, CH), 5.81 (s, 1H,
pyrimidine-H), 6.84 (d, J = 8.4 Hz, 2H), 7.10 (d, J = 8.4 Hz, 2H),
7.32 (d, J = 8.0 Hz, 1H), 7.36 (d, J = 8.0 Hz, 1H), 7.48
(t, J = 7.2 Hz, 1H), 8.37 (d, J = 7.6 Hz, 1H), 10.13 (br, 1H, NH);
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

March 2014
Synthesis and Herbicidal Activity of 2-Aroxy-propanamides Containing Pyrimidine and
1,3,4-Thiadiazole Rings
435
REFERENCES AND NOTES
IR (KBr) n: 3439 (NH), 2920 (ArH), 1684 (C=O), 1612, 1569,
1508 (Ar), 1352, 1222, 1195 (C—O—C) cmÀ1; EIMS (70 eV):
m/z 493 (M+, 12.5), 387 (40.3), 386 (14.8), 358 (33.8), 331
(17.2), 258 (74.3), 218 (16.8), 195 (22.8), 139 (18.6), 135
(59.4), 108 (32.7), 107 (41.9), 91 (100), 69 (26.8). Anal. Calcd
for C24H23N5O5S: C, 58.41; H, 4.70; N, 14.19. Found: C,
58.65; H, 4.61; N, 14.03.
[1] Hirai, K.; Uchida, A.; Ohno, R. Ed. Major synthetic routes for
modern herbicide class and agrochemical characteristics. In “Herbicide
Classes in Development,” Mode of Action, Targets, Genetic Engineering,
Chemistry [C]; Springer-Verlag: Berlin, 2004; pp. 179.
[2] Shimizu, T. J Pestic Sci 1997, 22, 254.
[3] Tamaru, M.; Inoue, J.; Hanai, R. J Agric Food Chem 1997,
45, 2777.
Compound 4h. 4h (Ar=4-CH3OC6H4): light yellow solid,
yield: 75%, mp 161–163ꢀC; 1H-NMR (CDCl3, 400 MHz) d:
1.64 (d, J = 6.8 Hz, 3H, CH3), 3.72 (s, 3H, OCH3), 3.83 (s, 6H,
2 Â OCH3), 4.88 (q, J = 6.8 Hz, 1H, CH), 5.80 (s, 1H,
pyrimidine-H), 6.83 (d, J = 8.0 Hz, 2H), 6.90 (d, J = 8.0 Hz, 2H),
7.33 (d, J = 8.0 Hz, 1H), 7.36 (d, J = 8.0 Hz, 1H), 7.50
(t, J = 7.6 Hz, 1H), 8.37 (d, J = 7.6 Hz, 1H), 10.33 (br, 1H, NH);
IR (KBr) n: 3440 (NH), 2928 (ArH), 1681 (C=O), 1613, 1572,
1505 (Ar), 1357, 1225, 1190 (C—O—C) cmÀ1; EIMS (70 eV):
m/z 509 (M+, 19.7), 387 (16.1), 386 (60.4), 358 (54.6), 331
(20.4), 299 (17.4), 259 (15.7), 258 (36.8), 195 (13.2), 151
(29.4), 139 (19.8), 135 (32.2), 124 (28.0), 123 (100), 121
(10.5), 92 (44.8), 77 (52.5). Anal. Calcd for C24H23N5O6S: C,
56.57; H, 4.55; N, 13.74. Found: C, 56.77; H, 4.30; N, 13.56.
Compound 4i. 4i (Ar=2,4-Cl2C6H3): white solid, yield: 63%,
mp 187–189ꢀC; 1H-NMR (CDCl3, 600 MHz) d: 1.71 (d, J = 7.2 Hz,
3H, CH3), 3.83 (s, 6H, 2 Â OCH3), 4.95 (q, J = 6.6 Hz, 1H, CH),
5.80 (s, 1H, pyrimidine-H), 6.92 (d, J = 8.4 Hz, 1H), 7.20 (d,
J = 9.0 Hz, 1H), 7.32 (d, J = 8.4 Hz, 1H), 7.36 (t, J = 7.8 Hz, 1H),
7.44 (s, 1H), 7.50 (t, J = 7.8 Hz, 1H), 8.36 (d, J = 7.8Hz, 1H),
10.43 (br, 1H, NH); IR (KBr) n: 3441 (NH), 2934 (ArH), 1676
(C=O), 1605, 1574, 1501 (Ar), 1342, 1228, 1184 (C—O—C)
cmÀ1. Anal. Calcd for C23H19Cl2N5O5S: C, 50.37; H, 3.49; N,
12.77. Found: C, 50.14; H, 3.24; N, 12.52.
[4] Tamaru, M.; Takehi, T.; Masuyama, N. Pestic Sci 1996,
47, 327.
[5] Tomlin, C. D. S. Ed. The Pesticide Manual, A World
Compendium, 14th Edition; British Crop Production Council: Hampshire,
UK, 2006; pp. 911.
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Acknowledgment. This work was supported by the Natural
Science Foundation of China (No. 20872046) and the Natural
Science Foundation of Hubei Province (No. 2008CDB086).
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet