Synthesis and fungicidal activities of 2-alkylthio-5-phenylmethylene-4h- imidazol-4-ones

Article abstract of DOI:10.1080/713744555

2-Alkylthio-5-phenylmethylidene-4H-imidazol-4-ones4weresynthesizedbyS- alkylationof2-thioxo-3-aryl-4-imidazolidinones3, whichwereobtainedviacyclizationofisothiocyanate2witharomaticprimaryamines. 3and4exhibitedgoodfungicidalactivityagainstPhysalosporapiricola.

Full text of DOI:10.1080/713744555

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Phosphorus, Sulfur, and Silicon and the Related
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Synthesis and Fungicidal Activities of 2-Alkylthio-5-
phenylmethylene-4H-imidazol-4-ones
Yong Sun a & Ming-Wu Ding b
a Yunyang Teachers College , Danjiangkou, P.R. China
b Central China Normal University , Wuhan, P.R. China
Published online: 27 Oct 2010.
To cite this article: Yong Sun & Ming-Wu Ding (2003) Synthesis and Fungicidal Activities of 2-Alkylthio-5-phenylmethylene-4H-
imidazol-4-ones, Phosphorus, Sulfur, and Silicon and the Related Elements, 178:10, 2137-2145, DOI: 10.1080/713744555
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Phosphorus, Sulfur, and Silicon, 178:2137–2145, 2003
ꢀC
Copyright Taylor & Francis Inc.
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426500390221609
SYNTHESIS AND FUNGICIDAL ACTIVITIES
OF 2-ALKYLTHIO-5-PHENYLMETHYLENE-4H-
IMIDAZOL-4-ONES
Yong Suna and Ming-Wu Dingb
Yunyang Teachers College, Danjiangkou, P.R. Chinaa and
Central China Normal University, Wuhan, P.R. Chinab
(Received January 8, 2003; accepted March 21, 2003)
2-Alkylthio-5-phenylmethylidene-4H-imidazol-4-ones 4 were synthe-
sized by S-alkylation of 2-thioxo-3-aryl-4-imidazolidinones 3, which
were obtained via cyclization of isothiocyanate 2 with aromatic pri-
mary amines. 3 and 4 exhibited good fungicidal activity against
Physalospora piricola.
Keywords: 4H-Imidazol-4-ones; alkylation; aza-Wittig reaction; fungi-
cidal activities; synthesis
4H-Imidazol-4-ones are important heterocycles having biological
and pharmaceutical activities,1−3 and some 2-alkylthioimidazolones
show significant fungicidal activities.4−6 However, most of the
2-alkylthioimidazolones reported are of the 5,5-disubstituted type and
were generally synthesized from corresponding α-amino acetic acid6,7
(Eq. 1). Unfortunately, 5-arylmethylidene-2-alkylthioimidazolones can-
not be prepared by this general method for the corresponding start-
ing material needed would be unstable vinyl amino acetic acids.
Recently, we are interested in the synthesis of biologically active
imidazolones via tandem aza-Wittig reaction.8−10 Here we report
a new efficient synthesis and fungicidal activity of some new
5-arylmethylidene-2-alkylthioimidazolone derivatives from the stable
vinyliminophosphorane 1.
We gratefully acknowledge financial support of this work by the Natural Science
Foundation of China (Project No. 20102001).
Address correspondence to Yong Sun, Department of Chemistry, Yunyang Teachers
College, Danjiangkou, 442700, P.R. China. E-mail: sunyong6111@sina.com
2137

2138
Y. Sun and M.-W. Ding
(1)
RESULTS AND DISCUSSION
The easily accessible vinyliminophosphorane 1 reacted with carbon
disulfide to give vinyl isothiocyanate 2. The reaction of 2 with aromatic
primary amines took place at refluxing acetonitrile in the presence of
potassium carbonate to give 2-thioxo-4-imidazolidinones 3 in 75–85%
yields (Table I).
(2)
TABLE I Preparation of 2-Thioxo-4-imidazolidinones 3 and
4H-Imidazol-4-ones 4
Entry
Ar
RX
Condition
Yield (%)a
m.p. (◦C)
3a
3b
4a
4b
4c
4d
4e
4f
4g
4h
4i
4j
4k
4l
Ph
3-Cl-Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
3-Cl-Ph
3-Cl-Ph
3-Cl-Ph
80◦C/2 h
80◦C/2 h
60◦C/4 h
50◦C/6 h
50◦C/10 h
50◦C/8 h
r.t./3 h
85
75
80
75
69
71
79
70
90
81
85
74
75
81
66
79
77
61
207–208
244–245
121–122
125–126
146–147
71–72
153–155
127–128
184–185
174–175
147–148
225–227
161–163
111–113
202–203
157–159
139–140
91–93
n-BuBr
n-PrBr
i-PrBr
n-C6H13Br
MeI
EtI
PhCH2Cl
r.t./2 h
50◦C/3 h
50◦C/2 h
50◦C/2 h
50◦C/3 h
r.t./2 h
ClCH2CN
ClCH2COOEt
ClCH2CONH2
BrCH2COOMe
BrCH(Me)COOEt
BrCH2COPh
MeI
50◦C/2 h
r.t./2 h
4m
4n
4o
4p
r.t./5 h
ClCH2COOEt
BrCH(Me)COOEt
50◦C/2 h
50◦C/2 h
aA: Isolated yields of 3a–3b based on vinyliminophosphorane 1. B: Purified yields of
4a–4m based on 2-thioxo-4-imidazolidinone 3a. C: Purified yields of 4n–4p based on
2-thioxo-4-imidazolidinone 3b.

Synthesis and Fungicidal Activities
2139
S-Alkylation of 3 with alkyl halides in presence of potassium carbon-
ate provided 2-alkylthio-5-phenylmethylidene-4H-imidazol-4-ones 4 in
61–90% yields. When activated alkylating reagents (RI, BrCH2COR)
were used, the alkylation could be carried out at room temperature.
When other alkylating reagents were applied, the alkylation had to be
carried out at 50–60◦C (Table I).
(3)
The structure of 3 and 4 has been characterized spectroscopically. For
example, the 1H NMR spectral data in 4e show the signals of CH and
SCH3 at 7.00 ppm and 2.67 ppm as single absorption respectively.
The chemical shift of aryl hydrogens is 8.16–7.27 ppm with multiple
absorption. In the IR spectral data of 4e, the strong stretching peak
of imidazolone C O appears at 1720 cm−1. The stretching vibration of
C C shows relatively strong absorbtion at about 1633 cm−1 due to a
resonance effect. The MS of 4e shows relatively strong molecule ion
peak at m/z 295 with 20% abundance.
The formation of 3 can be rationalized in terms of an initial nucle-
ophilic addition of aromatic primary amines to give the intermediate 5
which directly cyclized to give 3 in presence of solid potassium carbon-
ate (Eq. 4).
(4)
The biological activity of 3 and 4 was investigated and the results
showed that they exhibited fungicidal activities, especially against
Physalospora piricola. For example, 4f and 4m showed 96% inhibition
of Physalospora piricola in 50 mg/L (see Table II).
EXPERIMENTAL
Melting points are uncorrected. MS were measured on a HP5988A spec-
trometer. IR were recorded on a PE-983 infrared spectrometer as KBr
pellets with absorption in cm−1. NMR were recorded in CDCl3 on a

2140
Y. Sun and M.-W. Ding
TABLE II The Fungicidal Activities of 4-Imidazolidinones 3 and
4H-Imidazol-4-ones 4 (50 mg/L, relative inhibition %)
Fusarium
oxysporum
Gibberella
zeae
Cercospora
beticola sacc
Physalospora
piricola
Pellicularia
sasakii
Entry
3a
3b
4a
4b
4c
4d
4e
4f
4g
4h
4i
4j
4k
4l
30
20
47
75
44
38
50
59
56
50
38
50
63
34
47
56
63
47
22
17
62
83
83
62
81
79
62
76
64
64
67
48
98
64
67
76
25
17
66
61
84
61
84
66
61
61
73
55
84
36
61
86
80
84
75
50
71
92
92
88
79
96
79
79
92
83
92
83
96
88
92
88
0
14
94
70
78
74
57
26
35
94
78
13
83
57
35
0
4m
4n
4o
4p
44
70
Varian XL-200 spectrometer and resonances are given in ppm (δ) rel-
ative to TMS. Elemental analyses were taken on a Perkin-Elmer 2400
CHN Elementary Analysis Instrument. CS2 is poisonous and a good
hood should be used.
Preparation of Vinyliminophosphorane 1
Vinyliminophosphorane 1 was prepared by the Staudinger reaction of
vinyl azide and triphenyl phosphine according to the literature report.11
m.p. 148–150◦C (Lit.11 m.p. 149◦C.)
Preparation of 2-Thioxo-3-aryl-4-imidazolidinones 3
To a solution of vinyliminophosphorane 112 (2.25 g, 5 mmol) in dry
methylene chloride (15 mL) was added excess carbon disufide (5 mL).
After the reaction mixture was refluxed for 28 h, the solvent was re-
moved under reduced pressure and ether/petroleum ether (1:2, 20 mL)
was added to precipitate triphenylphosphine oxide which was removed
by filtration. The filtrate was evaporated to give isothiocyanate 2,
which was used directly without further purification. To the solution
of 2 in CH3CN (15 mL) was added ArNH2 (5 mmol) and solid potas-
sium carbonate (0.05 g). The mixture was stirred for 2 h at refluxing

Synthesis and Fungicidal Activities
2141
temperature and filtered; the filtrate was then evaporated in vacua and
the residue was recrystallized from methylene chloride/petroleum ether
to give 2-thioxo-3-aryl-4-imidazolidinones 3.
2-Thioxo-3-pheny-5-phenylmethylene-4-imidazolidinone
(3a)
1
Yellow crystals, H NMR (CDCl3, 200 MHz) δ 8.99 (s, 1H, N H),
7.49–7.22 (m, 10H, Ar H), 6.80 (s, 1H, CH); IR (cm−1), 3217, 1744,
1645; MS (m/z), 280 (M+, 5%), 136 (17%), 117 (100%). Elemental Anal.
Calcd. for C16H12N2OS: C, 68.57; H, 4.28; N, 10.00. Found: C, 68.39; H,
4.17; N, 9.86.
2-Thioxo-3-(3-chloropheny)-5-phenylmethylene-4-
imidazolidinone (3b)
Yellow crystals, 1H NMR (CDCl3, 200 MHz) δ 8.84 (s, 1H, N H), 7.60–
7.22 (m, 9H, Ar H), 6.81 (s, 1H, CH); IR (cm−1), 3223, 1745, 1642;
MS (m/z), 314 (M+, 3%), 168 (12%), 117 (53%), 77 (99%), 45 (100%).
Elemental Anal. Calcd. for C16H11ClN2OS: C, 61.05; H, 3.50; N, 8.90.
Found: C, 59.97; H, 3.39; N, 9.08.
Preparation of 2-Alkylthio-4H-imidazol-4-ones 4
A mixture of 3 (4 mmol), alkyl halide (5 mmol) and solid potassium
carbonate (1.11 g, 8 mmol) in CH3CN (30 mL) was stirred for 2–10 h at
room temperature or 50–60◦C and filtered, the filtrate was condensed
and the residue was recrystallized from methylene chloride/petroleum
ether to give 2-alkylthio-4H-imidazol-4-ones 4.
2-(n-Butylthio)-3-pheny-5-phenylmethylene-4H-imidazol-
4-one (4a)
1
Yellow crystals, H NMR (CDCl3, 200 MHz) δ 8.17–7.22 (m, 10H,
Ar H), 6.99 (s, 1H, CH), 3.31 (t, 2H, SCH2, J = 7.3 Hz), 1.86–1.44 (m,
4H, CH2CH2), 0.99 (t, 3H, CH3, J = 7.3 Hz); IR (cm−1), 1728, 1635; MS
(m/z), 337 (M+ + 1, 2%), 280 (10%), 136 (37%), 117 (100%). Elemental
Anal. Calcd. for C20H20N2OS: C, 71.40; H, 5.99; N, 8.33. Found: C, 71.36;
H, 5.73; N, 8.48.
2-(n-Propylthio)-3-pheny-5-phenylmethylene-4H-imidazol-
4-one (4b)
1
Yellow crystals, H NMR (CDCl3, 200 MHz) δ 8.16–7.21 (m, 10H,
Ar H), 6.99 (s, 1H, CH), 3.29 (t, 2H, SCH2, J = 7.3 Hz), 1.92–1.81 (m,
2H, CH2), 1.08 (t, 3H, CH3, J = 7.3 Hz); IR (cm−1), 1723, 1635; MS (m/z),
323 (M+ + 1, 3%), 280 (10%), 136 (51%), 117 (100%). Elemental Anal.

2142
Y. Sun and M.-W. Ding
Calcd. for C19H18N2OS: C, 70.78; H, 5.63; N, 8.69. Found: C, 70.84; H,
5.72; N, 8.57.
2-(i-Propylthio)-3-pheny-5-phenylmethylene-4H-imidazol-
4-one (4c)
1
Yellow crystals, H NMR (CDCl3, 200 MHz) δ 8.15–7.20 (m, 10H,
Ar H), 6.99 (s, 1H, CH), 4.21–4.14 (m, 1H, SCH, J = 6.8 Hz), 1.50
(d, 6H, 2CH3, J = 6.8 Hz); IR (cm−1), 1721, 1632; MS (m/z), 323 (M+
+
1, 9%), 280 (19%), 136 (43%), 117 (100%). Elemental Anal. Calcd. for
C19H18N2OS: C, 70.78; H, 5.63; N, 8.69. Found: C, 70.60; H, 5.85; N,
8.74.
2-(n-Hexylthio)-3-pheny-5-phenylmethylene-4H-imidazol-
4-one (4d)
1
Yellow crystals, H NMR (CDCl3, 200 MHz) δ 8.16–7.21 (m, 10H,
Ar H), 6.99 (s, 1H, CH), 3.30 (t, 2H, SCH2, J = 7.3 Hz), 1.91–0.87 (m,
11H, (CH2)4CH3); IR (cm−1), 1718, 1636; MS (m/z), 365 (M+ + 1, 2%),
318 (4%), 281 (18%), 136 (18%), 117 (66%), 32 (100%). Elemental Anal.
Calcd. for C22H24N2OS: C, 72.49; H, 6.64; N, 7.69. Found: C, 72.45; H,
6.77; N, 7.62.
2-Methylthio-3-pheny-5-phenylmethylene-4H-imidazol-
4-one (4e)
1
Yellow crystals, H NMR (CDCl3, 200 MHz) δ 8.16–7.27 (m, 10H,
Ar H), 7.00 (s, 1H, CH), 2.67 (s, 3H, SCH3); IR (cm−1), 1720, 1633;
MS (m/z), 295 (M+ + 1, 20%), 248 (6%), 150 (72%), 135 (54%), 116 (34%),
77 (100%). Elemental Anal. Calcd. for C17H14N2OS: C, 69.36; H, 4.79;
N, 9.52. Found: C, 69.15; H, 4.69; N, 9.63.
2-Ethylthio-3-pheny-5-phenylmethylene-4H-imidazol-
4-one (4f)
1
Yellow crystals, H NMR (CDCl3, 200 MHz) δ 8.16–7.27 (m, 10H,
Ar H), 7.00 (s, 1H, CH), 3.32 (q, 2H, SCH2, J = 7.3 Hz), 1.47 (t, 3H,
CH3, J = 7.3 Hz); IR (cm−1), 1721, 1630; MS (m/z), 309 (M+ + 1, 10%),
280 (7%), 248 (3%), 204 (7%), 136 (53%), 117 (50%), 32 (100%). Elemen-
tal Anal. Calcd. for C18H16N2OS: C, 70.10; H, 5.23; N, 9.08. Found: C,
70.32; H, 5.18; N, 9.26.
2-Benzylthio-3-pheny-5-phenylmethylene-4H-imidazol-
4-one (4g)
1
Yellow crystals, H NMR (CDCl3, 200 MHz) δ 8.19–7.19 (m, 15H,
Ar H), 7.03 (s, 1H, CH), 4.55 (s, 2H, SCH2Ph); IR (cm−1), 1730, 1634;
MS (m/z), 371 (M+ + 1, 1%), 167 (3%), 116 (8%), 77 (61%), 32 (100%).

Synthesis and Fungicidal Activities
2143
Elemental Anal. Calcd. for C23H18N2OS: C, 74.57; H, 4.90; N, 7.56.
Found: C, 74.63; H, 4.78; N, 7.74.
2-Cyanomethylthio-3-pheny-5-phenylmethylene-4H-
imidazol-4-one (4h)
1
Yellow crystals, H NMR (CDCl3, 200 MHz) δ 8.15–7.21 (m, 10H,
Ar H), 7.11 (s, 1H, CH), 4.04 (s, 2H, SCH2CN); IR (cm−1), 2258, 1726,
1627; MS (m/z), 320 (M+ + 1, 10%), 280 (4%), 175 (15%), 144 (24%), 135
(100%), 116 (77%). Elemental Anal. Calcd. for C18H13N3OS: C, 67.69;
H, 4.10; N, 13.16. Found: C, 67.62; H, 4.32; N, 13.21.
2-Ethoxycarbonylmethylthio-3-pheny-5-phenylmethylene-
4H-imidazol-4-one (4i)
1
Yellow crystals, H NMR (CDCl3, 200 MHz) δ 8.13–7.22 (m, 10H,
Ar H), 7.02 (s, 1H, CH), 4.24 (q, 2H, COOCH2, J = 7.3 Hz),
4.05 (s, 2H, SCH2COO), 1.30 (t, 3H, CH3, J = 7.3 Hz); IR (cm−1),
1737, 1722, 1634; MS (m/z), 367 (M+ + 1, 9%), 294 (14%), 248
(5%), 135 (37%), 116 (92%), 77 (100%). Elemental Anal. Calcd. for
C20H18N2O3S: C, 65.56; H, 4.95; N, 7.64. Found: C, 65.43; H, 4.74; N,
7.83.
2-Aminocarbonylmethylthio-3-pheny-5-phenylmethylene-
4H-imidazol-4-one (4j)
1
Yellow crystals, H NMR (CDCl3, 200 MHz) δ 8.08–7.22 (m, 10H,
Ar H), 7.08 (s, 1H, CH), 5.51 (s, 2H, NH2), 3.91 (s, 2H, SCH2CO); IR
(cm−1), 3305, 3261, 1709, 1678, 1630; MS (m/z), 338 (M+ + 1, 2%), 280
(2%), 193 (2%), 135 (7%), 116 (26%), 77 (32%), 32 (100%). Elemental
Anal. Calcd. for C18H15N3O2S: C, 64.08; H, 4.48; N, 12.45. Found: C,
64.30; H, 4.37; N, 12.63.
2-Methoxycarbonylmethylthio-3-pheny-5-
phenylmethylene-4H-imidazol-4-one (4k)
1
Yellow crystals, H NMR (CDCl3, 200 MHz) δ 8.13–7.22 (m, 10H,
Ar H), 7.02 (s, 1H, CH), 4.04 (s, 2H, SCH2COO), 3.79 (s, 3H, CH3);
IR (cm−1), 1737, 1724, 1637; MS (m/z), 353 (M+ + 1, 12%), 294 (14%),
248 (4%), 208 (8%), 135 (44%), 116 (75%), 32 (100%). Elemental Anal.
Calcd. for C19H16N2O3S: C, 64.76; H, 4.58; N, 7.95. Found: C, 64.63; H,
4.56; N, 8.12.
2-Ethoxycarbonyl(methyl)methylthio-3-pheny-5-
phenylmethylene-4H-imidazol-4-one (4l)
1
Yellow crystals, H NMR (CDCl3, 200 MHz) δ 8.13–7.21 (m, 10H,
Ar H), 7.00 (s, 1H, CH), 4.65 (q, 1H, SCHCOO, J = 7.7 Hz), 4.24–4.18

2144
Y. Sun and M.-W. Ding
(q, 2H, COOCH2, J = 7.7 Hz), 1.69 (d, 3H, CHCH3, J = 7.7 Hz), 1.24
(t, 3H, OCH2CH3, J = 7.7 Hz); IR (cm−1), 1739, 1723, 1635; MS (m/z),
381 (M+ + 1, 1%), 308 (2%), 280 (2%), 136 (6%), 116 (18%), 44 (100%).
Elemental Anal. Calcd. for C21H20N2O3S: C, 66.30; H, 5.30; N, 7.36.
Found: C, 66.17; H, 5.58; N, 7.19.
2-Benzoylmethylthio-3-pheny-5-phenylmethylene-4H-
imidazol-4-one (4m)
1
Yellow crystals, H NMR (CDCl3, 200 MHz) δ 8.09–7.03 (m, 15H,
Ar H), 6.96 (s, 1H, CH), 4.77 (s, 2H, SCH2COPh); IR (cm−1), 1721,
1694, 1634; MS (m/z), 399 (M+ + 1, 1%), 294 (3%), 135 (6%), 116
(12%), 105 (71%), 32 (100%). Elemental Anal. Calcd. for C24H18N2O2S:
C, 72.34; H, 4.55; N, 7.03. Found: C, 72.38; H, 4.37; N, 7.26.
2-Methylthio-3-(3-chloropheny)-5-phenylmethylene-4H-
imidazol-4-one (4n)
Yellow crystals, 1H NMR (CDCl3, 200 MHz) δ 8.15–7.21 (m, 9H,
Ar H), 7.00 (s, 1H, CH), 2.70 (s, 3H, SCH3); IR (cm−1), 1716, 1637;
MS (m/z), 329 (M+ + 1, 2%), 184 (4%), 170 (4%), 116 (6%), 44 (100%).
Elemental Anal. Calcd. for C17H13ClN2OS: C, 62.10; H, 3.98; N, 8.52.
Found: C, 62.26; H, 3.74; N, 8.64.
2-Ethoxycarbonylmethylthio-3-(3-chloropheny)-5-
phenylmethylene-4H-imidazol-4-one (4o)
Yellow crystals, 1H NMR (CDCl3, 200 MHz) δ 8.12–7.19 (m, 9H,
Ar H), 7.02 (s, 1H, CH), 4.24 (q, 2H, COOCH2, J = 7.3Hz), 4.05 (s, 2H,
SCH2COO), 1.30 (t, 3H, CH3, J = 7.3 Hz); IR (cm−1), 1730, 1718, 1636;
MS (m/z), 401 (M+ + 1, 1%), 328 (1%), 154 (1%), 116 (5%), 31 (100%).
Elemental Anal. Calcd. for C20H17ClN2O3S: C, 59.92; H, 4.27; N, 6.99.
Found: C, 59.73; H, 4.17; N, 7.21.
2-Ethoxycarbonyl(methyl)methylthio-3-(3-chloropheny)-5-
phenylmethylene-4H-imidazol-4-one (4p)
Yellow crystals, 1H NMR (CDCl3, 200 MHz) δ 8.12–7.21 (m,
9H, Ar H), 7.01 (s, 1H, CH), 4.65 (q, 1H, SCHCOO, J = 7.7
Hz), 4.28–4.13 (q, 2H, COOCH2, J = 7.3 Hz), 1.70 (d, 3H, CHCH3,
J = 7.7 Hz), 1.28 (t, 3H, OCH2CH3, J = 7.3 Hz); IR (cm−1), 1742,
1716, 1636; MS (m/z), 415 (M+ + 1, 7%), 342 (15%), 314 (10%),
250 (5%), 144 (25%), 116 (100%). Elemental Anal. Calcd. for
C21H19ClN2O3S: C, 60.79; H, 4.62; N, 6.75. Found: C, 60.53; H, 4.83; N,
6.67.

Synthesis and Fungicidal Activities
2145
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