Synthesis and herbicidal activity of O,O-dimethyl-(3-phenacryloyloxy) alkyl phosphonates

Article abstract of DOI:10.1080/10426507.2011.559495

In an attempt to discover novel compounds with high biological activity and low toxicity, a series of new O,O-dimethyl-(3-phenacryloyloxy) alkyl phosphonates 4a-m have been designed and synthesized by the reaction of 3-phenacryloyl chloride with α-hydroxyalkyl phosphonate. All new compounds were characterized by elemental analysis, IR, and ¹H NMR spectroscopy as well as by mass spectrometry. The results of preliminary bioassay indicate that some of the target compounds have excellent inhibitory activities on Triticum aestivum (wheat) and Brassica napus L. (rape). Copyright Taylor and Francis Group, LLC.

Full text of DOI:10.1080/10426507.2011.559495

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Phosphorus, Sulfur, and Silicon and the
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Synthesis and Herbicidal Activity of
O,O-Dimethyl-(3-Phenacryloyloxy) Alkyl
Phosphonates
Tao Wang a , Hai Jin Huang b , Jin Luo a & Dan Hong Yu a
a Key Laboratory of Functional Small Organic Molecules, Ministry of
Education, College of Chemistry and Chemical Engineering, Jiangxi
Normal University, Nanchang, 330022, P. R. China
b College of Chemistry and Chemical Engineering, Shangrao Normal
University, Shangrao, 334001, P. R. China
To cite this article: Tao Wang , Hai Jin Huang , Jin Luo & Dan Hong Yu (2012) Synthesis and Herbicidal
Activity of O,O-Dimethyl-(3-Phenacryloyloxy) Alkyl Phosphonates, Phosphorus, Sulfur, and Silicon and
the Related Elements, 187:1, 135-141, DOI: 10.1080/10426507.2011.559495
To link to this article: http://dx.doi.org/10.1080/10426507.2011.559495
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Phosphorus, Sulfur, and Silicon, 187:135–141, 2012
Copyright ꢀC Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426507.2011.559495
SYNTHESIS AND HERBICIDAL ACTIVITY OF
O,O-DIMETHYL-(3-PHENACRYLOYLOXY) ALKYL
PHOSPHONATES
Tao Wang,1 Hai Jin Huang,2 Jin Luo,1 and Dan Hong Yu1
1Key Laboratory of Functional Small Organic Molecules, Ministry of Education,
College of Chemistry and Chemical Engineering, Jiangxi Normal University,
Nanchang, 330022, P. R. China
2College of Chemistry and Chemical Engineering, Shangrao Normal University,
Shangrao, 334001, P. R. China
GRAPHICAL ABSTRACT
Abstract In an attempt to discover novel compounds with high biological activity and low
toxicity, a series of new O,O-dimethyl-(3-phenacryloyloxy) alkyl phosphonates 4a–m have
been designed and synthesized by the reaction of 3-phenacryloyl chloride with α-hydroxyalkyl
phosphonate. All new compounds were characterized by elemental analysis, IR, and 1H NMR
spectroscopy as well as by mass spectrometry. The results of preliminary bioassay indicate that
some of the target compounds have excellent inhibitory activities on Triticum aestivum (wheat)
and Brassica napus L. (rape).
Keywords O,O-Dimethyl-(3-phenacryloyloxy) alkyl phosphonates; synthesis; herbicidal ac-
tivities
INTRODUCTION
Pyruvate dehydrogenase complex (PDHC) is already known to be a site of pesti-
cide action because it plays a pivotal role in cellular metabolism catalyzing the oxidative
decarboxylation of pyruvate and the subsequent acetylation of coenzyme A (CoA) to
acety-CoA.1–4 An attempt to design inhibitors of PDHC as herbicides using biochemical
reasoning was reported by Baillie et al.5 Series of acetyl phosphonates have been prepared as
mechanism-based inhibitors of PDHC because they are regarded as bioisosters of pyruvate
Received 13 August 2010; accepted 27 January 2011.
We gratefully acknowledge financial support of this work by the National Natural Science Foundation of
China (Project No. 20862007) and Natural Science Foundation of Jiangxi Province (No. 2010GZH1399).
Address correspondence to Tao Wang, College of Chemistry and Chemical Engineering, Jiangxi Normal
University, 99 Ziyang Road, Nanchang 330022, China. E-mail: wangtao1962@sohu.com
135

136
T. WANG ET AL.
(acetyl formate).6 Baillie et al. demonstrated that some acetylphosphonates showed modest
herbicidal activity due to the inhibition of PDHC. However, their activity was not suffi-
ciently high for full development as herbicides. In the course of our investigations for new
phosphonate derivatives with good biological activities, we have shown that certain substi-
tuted phenoxy acetoxy alkyl phosphonates possess good herbicide activities.7–9 To find new
phosphonates with better pesticide activity, the 3-phenacryloyloxy structural unit is intro-
duced into phosphonate molecules; thus, O,O-dimethyl-(3-phenacryloyloxy) alkyl phos-
phonates were synthesized by the reaction of 3-phenacryloyl chloride with α-hydroxyalkyl
phosphonates under mild conditions. The synthetic route is shown in Scheme 1.
Scheme 1
RESULTS AND DISCUSSION
Synthesis and Structure
The phosphonates 4 were synthesized by the multistep route outlined in Scheme 1.
The reaction of dialkyl H-phosphonates with aldehydes is a convenient method used to syn-
thesize α-hydroxyalkyl phosphonates. The addition of a base (triethylamine or KF/Al2O3)
was essential for the addition reaction. Without the use of triethylamine or KF/Al2O3 as a
catalyst, the reaction was slow and also the yields were very low. Compounds 4 were pre-
pared from the compound 2 and 3-phenacryloyl chloride 3 in the presence of triethylamine.
As the target phosphonate derivatives contain groups sensitive to acid, base, or water, such
as carboxylic esters, the reaction required conditions near room temperature and the use of
anhydrous solvents. All products 4 were purified by flash column chromatography on silica
gel.
1
The molecular structures of all new compounds prepared were confirmed by H
NMR, IR spectra, MS, and elemental analyses.
In the 1H NMR spectra of 4, the proton of the P-CH moiety in 4f–m exhibits a doublet,
while the protons in the P-OCH3 groups display only one signal as a doublet. The IR spectra
of all compounds showed normal stretching absorption bands indicating the existence of
Ph-H (∼2950 cm−1), C O (∼1710 cm−1), C C (∼1650 cm−1), P O (∼1250 cm−1),

O,O-DIMETHYL-(3-PHENACRYLOYLOXY) ALKYL PHOSPHONATES
137
P-O-C (∼1050 cm−1), and P-C (∼760 cm−1). The EI mass spectra of compounds 4a–m
gave the anticipated molecular ion peaks. The mass spectrum of 4a shows a molecular ion
peak at m/z = 270 with 11.89% abundance. The mass spectra of compounds 4a–m show
the strongest ion peak at m/z = 93 with 100% abundance. All the fragmentation ions of
4a–m are consistent with the structure of the corresponding compounds and can be clearly
assigned.
Herbicidal Activities
The herbicidal activities of compounds 4a–m were evaluated at a rate of 100 and
10 ppm in a set of experiments. They were tested for stalk and root inhibitory effect
against Triticum aestivum (wheat) and Brassica napus L. (rape). As is evident from Table
1, compounds 4a,b,d–f and 4i exhibit notable herbicidal activity on the root of rape at
100 ppm, while compounds 4a,b,e,g–j obviously have a promotive action for plant growth
against a stalk of wheat at 10 ppm.
EXPERIMENTAL
General remarks: Melting points are uncorrected. Mass spectra were measured with
a Finnigan Trace MS spectrometer. IR spectra were recorded with a PE-983 infrared spec-
1
trophotometer as KBr pellets. H and 31P NMR spectra were recorded in CDCl3 with a
Varian Mercury 400 spectrometer and resonances are given relative to external Tetramethyl-
silane (TMS) and 85% H3PO4, respectively. Elementary analyses were performed with a
Vario EL III elementary analysis instrument. The reagents and solvents were commercially
available and were purified according to conventional methods before use. Compounds 1,
2, and 3 were prepared according to the literature.10–22
Table 1 The inhibition percentage of phosphonates 4 to wheat and rape∗
Wheat
Rape
Stalk 10 ppm,
100 ppm
Root 10 ppm,
100 ppm
Stalk 10 ppm,
100 ppm
Root 10 ppm,
100 ppm
4
R
a
b
c
d
e
f
g
h
i
H
Me
Et
Pr
iPr
Ph
4-CH3C6H4
4-ClC6H4
2-ClC6H4
2,4-Cl2C6H3
4-MeOC6H4
3-NO2C6H4
2-Furyl
−20.98
−12.46
−56.96
−36.96
0.00
−2.45
45.28
10.75
25.53
33.40
49.81
79.25
−9.43
−14.72
40.57
0.00
51.22
24.34
37.25
61.48
61.27
41.9
78.94
58.52
41.69
49.95
−12.70
84.13
75.56
98.12
91.00
−4.59
0.00
−15.08
−0.98
−21.64
5.57
−48.30
−4.75
22.64
−0.18
23.77
12.08
3.96
92.33
64.02
89.74
96.30
96.83
67.20
79.89
91.00
0.00
2.95
12.05
8.07
10.49
−8.20
−6.56
4.92
−12.79
−15.08
12.79
−5.25
−7.87
−0.33
30.87
−13.10
−32.28
−1.17
−31.11
−35.79
−39.65
−30.88
−16.14
−3.51
9.71
−7.37
22.81
37.78
28.54
28.19
−21.29
−35.21
−43.04
0.00
−4.59
−18.36
−13.77
6.56
1.89
24.34
2.26
40.94
90.57
−4.53
89.54
j
k
l
−8.20
33.21
78.68
0.00
72.91
81.16
0.00
0.00
m
2.62
38.56
−2.11
2,4-D
78.97
92.12
91.20
98.50
∗Negative inhibition percentage shows promotive action for plant growth.

138
T. WANG ET AL.
Synthesis of O,O-Dimethyl-(3-Phenacryloyloxy) Alkyl Phosphonates 4:
General Procedure
A solution of 3-phenacryloyl chloride 3 (22 mmol) in CH2Cl2 (10 mL) was added to
a stirred mixture of α-hydroxyalkyl phosphonate 2 (20 mmol) and triethylamine (22 mmol)
in CH2Cl2 (25 mL) at 20 ◦C–25 ◦C. The mixture was stirred at ambient temperature for 4 h
and then at 40 ◦C for 1 h, and was washed with 0.1 M hydrochloric acid, saturated sodium
hydrogen carbonate solution, and brine. The resulting mixture was dried and the solvent
was evaporated. The residue was chromatographed on silica with acetone/petroleum ether
(60 ◦C–90 ◦C) (1:4) as eluent to give compounds 4.
(Dimethoxyphosphoryl)Methyl Cinnamate (4a)
Pale yellow liquid, yield 61%; nD20: 1.5490. IR (KBr): υ = 3062 (w, Ph-H), 2957,
2854 (m, C-H), 1723 (s, C O), 1635 (C C), 1578, 1496, 1450 (s, Ph), 1261 (s, P O),
1161 (s, C-O-C), 1031, 896 (s, P-O-C), 768 (s, P-C) cm−1. 1H NMR (CDCl3, 400 MHz): δ
= 3.84 (d, J = 10.8 Hz, 6H, OCH3), 4.54 (d, J = 8.4 Hz, 2H, -OCH2P), 6.48 (d, J = 16.0
Hz, 1H, PhCH CH-), 7.40–7.55 (m, 5H, C6H5), 7.74 (d, J = 16.0 Hz, 1H, PhCH CH-).
31P NMR (CDCl3): δ = 22.0 ppm. MS (70 eV), m/z (%): 270 (M+ 11.89); Anal. calcd. for
C12H15O5P: C, 53.34; H, 5.60. Found: C, 53.43; H, 5.72%.
1-(Dimethoxyphosphoryl)Ethyl Cinnamate (4b)
Pale yellow liquid, yield 83%; nD20: 1.5480. IR (KBr), υ = 3061 (w, Ph-H), 2956,
2854 (m, C-H), 1720 (s, C O), 1636 (C C), 1578, 1496, 1450 (s, Ph), 1247 (s, P O),
1163 (s, C-O-C), 1051, 894 (s, P-O-C), 768 (s, P-C) cm−1; 1H NMR (CDCl3, 400 MHz):
δ = 1.55 (d, J = 9.6 Hz, 3H, -CH3), 3.84 (d, J = 6.8 Hz, 6H, OCH3), 5.46 (m, 1H, -OCHP),
6.47 (d, J = 16.0 Hz, 1H, PhCH CH-), 7.37–7.55 (m, 5H, C6H5), 7.73 (d, J = 16.0 Hz,
1H, PhCH CH-). 31P NMR (CDCl3): δ = 21.8 ppm. MS (70 eV), m/z (%): 284 (M+
12.22); Anal. calcd. for C13H17O5P: C, 54.93; H, 6.03. Found: C, 54.77; H, 6.16%.
1-(Dimethoxyphosphoryl)Propyl Cinnamate (4c)
Pale yellow liquid, yield 80%; nD20: 1.5370. IR (KBr), υ = 3062 (w, Ph-H), 2956,
2854 (m, C-H), 1716 (s, C O), 1635 (C C), 1578, 1496, 1450 (s, Ph), 1257 (s, P O),
1159 (s, C-O-C), 1031, 939 (s, P-O-C), 768 (s, P-C) cm−1; 1H NMR (CDCl3, 400 MHz):
δ = 1.16 (t, J = 9.6 Hz, 3H, -CH2CH3), 2.02 (m, 2H, -CH2CH3), 3.82 (d, J = 8.4 Hz, 6H,
OCH3), 5.38 (m, 1H, -OCHP), 6.49 (d, J = 16.0 Hz, 1H, PhCH CH-), 7.40–7.56 (m, 5H,
C6H5), 7.75 (d, J = 16.0 Hz, 1H, PhCH CH-). 31P NMR (CDCl3): δ = 21.5 ppm. MS (70
eV), m/z (%): 298 (M+ 15.86); Anal. calcd. for C14H19O5P: C, 56.37; H, 6.42. Found: C,
56.55; H, 6.50%.
1-(Dimethoxyphosphoryl)Butyl Cinnamate (4d)
Pale yellow liquid, yield 78%; nD20: 1.5345. IR (KBr), υ = 3062 (w, Ph-H), 2959,
2874 (m, C-H), 1715 (s, C O), 1635 (C C), 1578, 1496, 1450 (s, Ph), 1263 (s, P O),
1
1160 (s, C-O-C), 1032, 985 (s, P-O-C), 709 (s, P-C) cm−1; H NMR (CDCl3, 400 Hz):
δ = 0.96 (t, J = 8.4 Hz, 3H, -CH2CH2CH3), 1.60 (m, 2H, -CH2CH2CH3), 1.93 (m, 2H,

O,O-DIMETHYL-(3-PHENACRYLOYLOXY) ALKYL PHOSPHONATES
139
-CH2CH2CH3), 3.81 (d, J = 6.8 Hz, 6H, OCH3), 5.48 (m, 1H, -OCHP), 6.48 (d, J =
16.0 Hz, 1H, PhCH CH-), 7.39–7.55 (m, 5H, C6H5), 7.74 (d, J = 16.0 Hz, 1H, PhCH
CH-).31P NMR (CDCl3): δ = 21.1 ppm. MS (70 eV), m/z (%): 312 (M+ 15.27); Anal.
calcd. for C15H21O5P: C, 57.69; H, 6.78. Found: C, 57.75; H, 6.90%.
1-(Dimethoxyphosphoryl)-2-Methylpropyl Cinnamate (4e)
Pale yellow liquid, yield 74%; nD20: 1.5350. IR (KBr): υ = 3062 (w, Ph-H), 2963,
2854 (m, C-H), 1716 (s, C O), 1634 (C C), 1578, 1496, 1451 (s, Ph), 1245 (s, P O),
1159 (s, C-O-C), 1033, 893 (s, P-O-C), 768 (s, P-C) cm−1; 1H NMR (CDCl3, 400 MHz):
δ = 1.08 (d, J = 7.2 Hz, 6H, -CH(CH3)2), 2.31 (m, 1H, -CH(CH3)2), 3.79 (d, J = 5.6 Hz,
6H, OCH3), 5.29 (m, 1H, -OCHP), 6.50 (d, J = 16.0 Hz, 1H, PhCH CH-), 7.40–7.55 (m,
5H, C6H5), 7.75 (d, J = 16.0 Hz, 1H, PhCH CH-). 31P NMR (CDCl3): δ = 21.2 ppm. MS
(70 eV), m/z (%): 312 (M+ 11.73); Anal. calcd. for C15H21O5P: C, 57.69; H, 6.78. Found:
C, 57.58; H, 6.86%.
(Dimethoxyphosphoryl)(Phenyl)Methyl Cinnamate (4f)
Pale yellow liquid, yield 71%; nD20: 1.5525. IR (KBr), υ = 3063 (w, Ph-H), 2956,
2854 (m, C-H), 1731 (s, C O), 1633 (C C), 1578, 1496, 1450 (s, Ph), 1265 (s, P O),
1151 (s, C-O-C), 1045, 910 (s, P-O-C), 768 (s, P-C) cm−1; 1H NMR (CDCl3, 400 MHz):
δ = 3.68 (d, J = 10.4 Hz, 6H, OCH3), 6.30 (d, J = 13.2 Hz, 1H, -OCHP), 6.56 (d, J =
16.4 Hz, 1H, PhCH CH-), 7.33–7.57 (m, 10H, -C6H5), 7.77 (d, J = 16.0 Hz, 1H, PhCH
CH-).31P NMR (CHCl3): δ = 19.7 ppm. MS (70 eV) m/z (%): 346 (M+ 13.10); Anal. calcd.
for C18H19O5P: C, 62.43; H, 5.53. Found: C, 62.56; H, 5.61%.
(Dimethoxyphosphoryl)(p-Tolyl)Methyl Cinnamate (4g)
◦
◦
Colorless crystals, yield 64%; mp: 67 C–70 C. IR (KBr): υ = 3072 (w, Ph-H),
2958, 2857 (m, C-H), 1704 (s, C O), 1637 (C C), 1577, 1498, 1448 (s, Ph), 1237 (s,
P O), 1177 (s, C-O-C), 1057, 951 (s, P-O-C), 768 (s, P-C) cm−1; 1H NMR (CDCl3, 400
MHz): δ = 2.35 (s, 3H, CH3), 3.75 (d, J = 10.4 Hz, 6H, OCH3), 6.26 (d, J = 13.2 Hz, H,
-OCHP), 6.54 (d, J = 16.0 Hz, 1H, PhCH CH-), 7.19–7.56 (m, 9H, C6H5, C6H4), 7.75
(d, J = 16.4 Hz, 1H, PhCH CH-).31P NMR (CDCl3): δ = 19.9 ppm. MS (70 eV), m/z
(%): 360 (M+ 15.82); Anal. calcd. for C19H21O5P: C, 63.33; H, 5.87. Found: C, 63.51; H,
5.94%.
(4-Chlorophenyl)(Dimethoxyphosphoryl)Methyl Cinnamate (4h)
◦
◦
Colorless crystals, yield 69%; mp: 79 C–82 C. IR (KBr): υ = 3096 (w, Ph-H),
2928, 2852 (m, C-H), 1729 (s, C O), 1635(C C), 1576, 1488, 1449 (s, Ph), 1257 (s,
P O), 1181 (s, C-O-C), 1061, 892 (s, P-O-C), 767 (s, P-C) cm−1; 1H NMR (CDCl3, 400
MHz): δ = 3.73 (d, J = 10.8 Hz, 6H, OCH3), 6.24 (d, J = 13.6 Hz, 1H, -OCHP), 6.54 (d,
J = 16.0 Hz, 1H, PhCH CH-), 7.36–7.56 (m, 9H, C6H5, C6H4), 7.76 (d, J = 16.0 Hz, 1H,
PhCH CH-). 31P NMR (CDCl3): δ = 19.7 ppm. MS (70 eV), m/z (%): 380 (M+ 19.26);
Anal. calcd. for C18H18ClO5P: C, 56.78; H, 4.76. Found: C, 56.82; H, 4.86%.

140
T. WANG ET AL.
(2-Chlorophenyl)(Dimethoxyphosphoryl)Methyl Cinnamate (4i)
Pale yellow liquid, yield 58%; nD20: 1.5745. IR (KBr), υ = 3063 (w, Ph-H), 2956,
2854 (m, C-H), 1732 (s, C O), 1633 (C C), 1577, 1472, 1449 (s, Ph), 1264 (s, P O),
1149 (s, C-O-C), 1035, 890 (s, P-O-C), 767 (s, P-C) cm−1; 1H NMR (CDCl3, 400 MHz):
δ = 3.84 (d, J = 10.8 Hz, 6H, OCH3), 6.54 (d, J = 16.0 Hz, 1H, PhCH CH-), 6.78 (d,
J = 13.6 Hz, 1H, -OCHP), 7.28–7.55 (m, 9H, C6H5, C6H4), 7.75 (d, J = 16.0 Hz, 1H,
PhCH CH-). 31P NMR (CDCl3): δ = 20.0 ppm. MS (70 eV), m/z (%): 380 (M+ 17.46);
Anal. calcd. for C18H18ClO5P: C, 56.78; H, 4.76. Found: C, 56.87; H, 4.89%.
(2,4-Dichlorophenyl)(Dimethoxyphosphoryl)Methyl Cinnamate (4j)
Pale yellow liquid, yield 75%; nD20: 1.5635. IR (KBr), υ = 3063 (w, Ph-H), 2956,
2855 (m, C-H), 1728 (s, C O), 1635 (C C), 1589, 1473, 1452 (s, Ph), 1268 (s, P O),
1139 (s, C-O-C), 1037, 846 (s, P-O-C), 767 (s, P-C) cm−1; 1H NMR (CDCl3, 400 MHz):
δ = 3.80 (d, J = 11.2 Hz, 6H, OCH3), 6.52 (d, J = 16.0 Hz, 1H, PhCH CH-), 6.68 (d,
J = 13.6 Hz, 1H, -OCHP), 7.30–7.67 (m, 8H, C6H5, C6H3), 7.75 (d, J = 16.0 Hz, 1H,
PhCH CH-). 31P NMR (CDCl3): δ = 19.2 ppm. MS (70 eV), m/z (%): 415 (M+ 24.16);
Anal. calcd. for C18H17Cl2O5P: C, 52.07; H, 4.13. Found: C, 52.22; H, 4.31%.
(Dimethoxyphosphoryl)(4-Methoxyphenyl)Methyl Cinnamate (4k)
◦
◦
Colorless crystals, yield 57%; mp: 76 C–80 C. IR (KBr): υ = 3026 (w, Ph-H),
2956, 2855 (m, C-H), 1705 (s, C O), 1638 (C C), 1583, 1498, 1448 (s, Ph), 1254 (s,
P O), 1177 (s, C-O-C), 1030, 882 (s, P-O-C), 767 (s, P-C) cm−1; 1H NMR (CDCl3, 400
MHz): δ = 3.62 (s, 3H, C6H4OCH3), 3.79 (d, J = 9.2 Hz, 6H, OCH3), 6.24 (d, J = 12.8
Hz, 1H, -OCHP), 6.53 (d, J = 16.0 Hz, 1H, PhCH CH-), 6.91–7.55 (m, 9H, C6H5, C6H4),
7.75 (d, J = 16.0 Hz, 1H, PhCH CH-). 31P NMR (CDCl3): δ = 19.6 ppm. MS (70 eV),
m/z (%): 376 (M+ 18.36); Anal. calcd. for C19H21O6P: C, 60.64; H, 5.62. Found: C, 60.73;
H, 5.71%.
(Dimethoxyphosphoryl)(3-Nitrophenyl)Methyl Cinnamate (4l)
Pale yellow liquid, yield 59%; nD20: 1.5850. IR (KBr): υ = 3065 (w, Ph-H), 2957,
2855 (m, C-H), 1732 (s, C O), 1634(C C), 1578, 1532, 1450 (s, Ph), 1265 (s, P O),
1148 (s, C-O-C), 1036, 907 (s, P-O-C), 768 (s, P-C) cm−1; 1H NMR (CDCl3, 400 MHz):
δ = 3.79 (d, J = 11.2 Hz, 6H, OCH3), 6.37 (d, J = 13.5 Hz, 1H, -OCHP), 6.58 (d, J =
16.0 Hz, 1H, PhCH CH-), 7.41–8.40 (m, 9H, C6H5, C6H4), 7.80 (d, J = 16.0 Hz, 1H,
PhCH CH-). 31P NMR (CDCl3): δ = 20.0 ppm. MS (70 eV), m/z (%): 391 (M+ 31.62);
Anal. calcd. for C18H18NO7P: C, 55.25; H, 4.64; N, 3.58. Found: C, 55.38; H, 4.73; N,
3.79%.
(Dimethoxyphosphoryl)(2-(Furan-2-yl)Phenyl)Methyl Cinnamate (4m)
Pale yellow liquid, yield 72%; nD20: 1.5625. IR (KBr), υ = 3062 (w, Ph-H), 2957,
2855 (m, C-H), 1723 (s, C O), 1635(C C), 1578, 1497, 1450 (s, Ph), 1270 (s, P O),
1151 (s, C-O-C), 1033, 935 (s, P-O-C), 767 (s, P-C) cm−1; 1H NMR (CDCl3, 400 MHz):
δ = 3.80 (d, J = 10.8 Hz, 6H, OCH3), 6.42 (d, J = 11.6 Hz, 1H, -OCHP), 6.50 (d, J =
16.0 Hz, 1H, PhCH CH-), 6.41–7.54 (m, 5H, C4H3O, C6H5), 7.76 (d, J = 16.0 Hz, 1H,

O,O-DIMETHYL-(3-PHENACRYLOYLOXY) ALKYL PHOSPHONATES
141
PhCH CH-). 31P NMR (CDCl3): δ = 16.7 ppm. MS (70 eV), m/z (%): 336 (M+ 21.62);
Anal. calcd. for C16H17O6P: C, 57.15; H, 5.10. Found: C, 57.32; H, 5.30%.
Herbicidal Testing
Herbicidal testing of the new compounds 4 was carried out in a plant (growth room
temperature 23 1 ◦C, RH 60 5%, light intensity 10 Klux, photoperiod 8 h/day). Twenty
seeds of each weed species including rape and wheat were chosen for testing. Seedlings
were grown in the 9-cm-diameter test plate containing two pieces of filter paper and 9
mL solution of the tested compound (100 and 10 mg/L, respectively). Distilled water and
2,4-dichlorophenoxyl acetic acid (2,4-D), a commercially available herbicide in the market,
were used as comparison compounds. The herbicidal activity was assessed as the inhibition
rate in comparison with the distilled water. The herbicidal rating score was based on visual
observation, ranging from 0% to 100%: 0% means no effect, 100% means complete killing.
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