Synthesis and biological activities of O, O-dialkyl 1-((4,6- Dichloropyrimidin-2-yl)carbamyloxy) alkylphosphonates

Article abstract of DOI:10.1080/10426507.2013.855774

(Equation present) A series of new 1-((4,6-dichloropyrimidin-2-yl) carbamyloxy) alkylphosphonates were designed and synthesized. The structures of all the title compounds were confirmed by IR, ¹H-NMR, ³¹P-NMR and elemental analysis. The results of the bioassay showed that all of title compounds exhibited weak herbicidal activities against monocotyledons and dicotyledons; however, some of them showed potential plant growth regulatory activities. 2014 Copyright Taylor & Francis Group, LLC.

Full text of DOI:10.1080/10426507.2013.855774

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Phosphorus, Sulfur, and Silicon and the
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Synthesis and Biological Activities of
O,O-Dialkyl 1-((4,6-Dichloropyrimidin-2-
yl)Carbamyloxy) Alkylphosphonates
Liang Xua, Geyun Youa, Hao Penga & Hongwu Hea
a Key Laboratory of Pesticide & Chemical Biology, Ministry of
Education, College of Chemistry, Central China Normal University,
Wuhan, China, Hubei
Accepted author version posted online: 23 Jan 2014.Published
online: 12 Jun 2014.
To cite this article: Liang Xu, Geyun You, Hao Peng & Hongwu He (2014) Synthesis and Biological
Activities of O,O-Dialkyl 1-((4,6-Dichloropyrimidin-2-yl)Carbamyloxy) Alkylphosphonates, Phosphorus,
Sulfur, and Silicon and the Related Elements, 189:6, 812-818, DOI: 10.1080/10426507.2013.855774
To link to this article: http://dx.doi.org/10.1080/10426507.2013.855774
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Phosphorus, Sulfur, and Silicon, 189:812–818, 2014
Copyright ꢀC Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426507.2013.855774
SYNTHESIS AND BIOLOGICAL ACTIVITIES
OF O,O-DIALKYL 1-((4,6-DICHLOROPYRIMIDIN-2-
YL)CARBAMYLOXY) ALKYLPHOSPHONATES
Liang Xu, Geyun You, Hao Peng, and Hongwu He
Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of
Chemistry, Central China Normal University, Wuhan, Hubei, China
GRAPHICAL ABSTRACT
Abstract A series of new 1-((4,6-dichloropyrimidin-2-yl)carbamyloxy) alkylphosphonates
were designed and synthesized. The structures of all the title compounds were confirmed by
IR, 1H-NMR, 31P-NMR and elemental analysis. The results of the bioassay showed that all of
title compounds exhibited weak herbicidal activities against monocotyledons and dicotyledons;
however, some of them showed potential plant growth regulatory activities.
Keywords Carbamyloxy; phosphonate; plant growth regulatory activity
INTRODUCTION
Pyrimidine compounds have received considerable attention over the past two decades
in medicine and pesticide chemistry due to their biological activities.1,2 Especially, more and
more pyrimidine compounds have been used as insecticides and herbicides, such as pyrim-
idine amines, pyrimidine acrylic esters, pyrimidine sulfonylureas, and triazolopyrimidine
sulfonamides.3
In our previous work, it was found that 1-(substituted phenoxyacetoxy)alkylphos
phonates or phosphinates possess good herbicidal activities and plant growth regula-
tory activity.2,3 In order to extend the structure type of alkylphosphonates and find
more bioactive compounds, a pyrimidine amine structural unit was introduced into the
molecule structure. Therefore, a novel series of O,O-dialkyl 1-((4,6-dichloropyrimidin-
2-yl)carbamyloxy)alkylphosphonates were synthesized and screened for their herbicidal
activities and plant growth regulatory activities. It is very interesting that all of these com-
pounds have weak herbicidal activities, however, some of them showed potential plant
growth regulating activities.
Received 4 August 2013; accepted 11 October 2013.
Address correspondence to Hao Peng and Hongwu He, College of Chemistry, Central China Normal
University, 152 Luoyu Road, Wuhan 430079, China. E-mail: penghao@mail.ccnu.edu.cn; he1208@mail.
ccnu.edu.cn
812

O,O-DIALKYL 1-((4,6-DICHLOROPYRIMIDIN-2-YL)CARBAMYLOXY)ALKYLPHOSPHONATES 813
RESULTS AND DISCUSSION
Syntheses
The multi-step procedure for the synthesis of the title phosphonates 6 is outlined in
Scheme 1. O,O-Dialkyl phosphonate 1 was accomplished in a one-step reaction starting
from phosphorus trichloride and the corresponding alcohol according to the literature.4
1-hydroxyalkylphosphonates 2 were prepared by the addition of 1 and several kinds of
aldehydes using triethylamine as a catalyst and gave yields of 60%–90%. 4,6-Dichloro-2-
isocyanatopyrimidine 5 were obtained by the reaction of 4,6-dichloropyrimidin-2-amine 4
with excess oxalyl chloride according to the literature.5 The title compounds 6 were then
obtained by the addition of compounds 2 with 4,6-dichloro-2-isocyanatopyrimidine 5. The
1
structures of 6a–p (Table 1) were confirmed by comprehensive IR, H-NMR, 31P-NMR,
and elemental analysis.
IR spectra of the title compounds 6a–p showed normal stretching absorption
bands, indicating the existence N–H (3310–3347 cm−1), P O (∼1220 cm−1), P C
(750–820 cm−1), P O C (1032–1070 cm−1), C O (∼1770 cm−1), C O (∼1170 cm−1),
1
Ar–H (∼3050 cm−1), and C H (3002–3041 cm−1). In the H-NMR spectra of the title
compounds 6a–p, the chemical shifts of aromatic protons appeared at 7.06–7.78 ppm.
As for compounds with aliphatic groups as R’, the proton signal corresponding to OCHP
displayed multiplets at 4.55–5.60 ppm; as for the compounds with aromatic groups as R’,
the proton signal appears at 6.11–6.81 ppm as doublets due to coupling with phospho-
rus. 31P-NMR chemical shifts of compounds 6a–p appeared as singlets at δ 13.3–23.6
ppm.
Biological Activity
The herbicidal activities of compounds 6a–p were evaluated at a dosage of 2.25 kg/ha
in greenhouse using the previously reported procedure.6 They were tested for pre-emergence
and post-emergence inhibitory effect against three monocotyledons (Triticum aestivum L.

814
L. XU ET AL.
Table 1 Structure and physical constants of compounds 6
No.
R
R’
m.p. (◦C)
Yield (%)
6a
6b
6c
6d
6e
6f
6g
6h
6i
6j
6k
6l
6m
6n
6o
6p
Me
Me
Me
Me
Me
Me
Me
Me
Me
Et
Et
Et
Et
i-Pr
i-Pr
i-Pr
H
Me
Et
n-Bu
Fur-2-yl
Ph
o-ClPh
p-ClPh
p-NO2Ph
Me
75–77
61
68
61
71
61
71
77
75
71
69
73
75
82
75
83
62
148–149
167–169
81–83
194–195
161–163
187–189
151–153
185–187
114–115
181–183
173–175
170–171
139–141
195–196
181–183
Ph
o-ClPh
p-ClPh
Me
Ph
Fur-2-yl
(wheat), Digitaria sanguinalis Scop (ascendant crabgrass) and Echinochloa crusgalli Beava
(barnyard grass)) and three dicotyledons (Brassica napus L. (rape), Cucumis sativus L.
(cucumber), and Amarantus mangestnus L. (amaranth)). Unfortunately, compounds 6a–p
have almost no inhibitory activities against both monocotyledons and dicotyledons. How-
ever, it is very interesting that compounds 6a–p present negative inhibition ratio (−2.3
to −68%) to some tested dicotyledonous plants. For example, 6c, 6f, 6l, and 6o showed
promoting effect on the growth of dicotyledonous plants (Table S1 in Supplementary
Materials).
Compounds 6a–p were further tested for plant growth regulatory activity by cucum-
ber cotyledon at the dosage of 10 ppm. As seen from Table S2, most of the compounds
6a–p had stimulating activities to the growth of cucumber cotyledon. The regulatory growth
index values clearly showed that 6a, 6c, 6n inhibited the growth of cucumber cotyledons
expansion. However, they displayed stimulating activities to the growth of cucumber cotyle-
dons root. The compound 6i inhibited both the growth of cucumber cotyledon expansion
and cucumber cotyledon root, and 6k exhibited higher stimulating activity to the growth of
cucumber cotyledon root than indole acetic acid (IAA) at the dosage of 10 ppm, but their
stimulating activity to the growth of cucumber cotyledon expansion at 10 ppm was lower
compared with that of kinetin (KT).
Herbicidal activities (Table S1) and plant growth regulatory activities (Table S2) are
presented in Supplementary Materials.
CONCLUSIONS
In conclusion, a series of 1-((4,6-dichloropyrimidin-2-yl)carbamyloxy)alkylphospho
nates were synthesized via the key intermediates 4,6-dichloro-2-isocyanatopyrimidine

O,O-DIALKYL 1-((4,6-DICHLOROPYRIMIDIN-2-YL)CARBAMYLOXY)ALKYLPHOSPHONATES 815
and 1-hydroxyphosphonates with satisfactory yields. Most of the synthesized compounds
showed weak herbicidal activities against the tested weeds for pre- or post-emergence, but
some of them showed promoting effect on the growth of dicotyledonous plants. The plant
growth regulatory activities of these compounds were tested on cucumber cotyledon at the
dosage of 10 ppm. The primary bioassay results indicated that compounds 6a–p showed
good to moderate plant growth regulatory activities. Especially, compound 6k exhibited
higher stimulating activity to the growth of cucumber cotyledon root than IAA, but their
stimulating activity to the growth of cucumber cotyledon expansion at 10 ppm was lower
compared with KT.
EXPERIMENTAL
1H, 13C-NMR, and 31P-NMR spectra were recorded on a Varian Mercury-Plus 200
spectrometer with CDCl3 as the solvent and TMS as the internal standard. Infrared spectra
were recorded in potassium bromide disks on a Nicolet Avatar 360 FTIR spectrometer.
Elemental analysis was performed by Elementar Vario EL III elementary analyzer. Mass
spectra were measured on Finnigan Trace MS 2000 spectrometer. Melting points (m.p.)
were measured on an electrothermal melting point apparatus and temperature uncorrected.
Synthesis
Synthesis of 2-aminopyrimidine-4,6-diol (3). 2-aminopyrimidine-4,6-diol 3
was prepared by the nucleophilic addition–elimination reaction of guanidine carbonate and
diethyl malonate using ethanol as solvent in 93% yield after refluxing 60 h.7
Synthesis of 4,6-dichloropyrimidin-2-amine (4) and 4,6-dichloro-2-
isocyanatopyrimidine (5). 4,6-dichloropyrimidin-2-amine 4 was synthesized by a
standard method.8 4,6-dichloro-2-isocyanatopyrimidine 5 was obtained as a reddish brown
liquid in 70% yield by treated compound 4 with four equivalent oxalyl chloride under
110◦C for 2 h.5
General Procedure for the Synthesis of Compounds 6
1-hydroxylalkylphosphonates 2 were obtained by the general method of our previ-
ously published papers.9–11 To a three-necked flask, compounds 2 (0.005 mol), 4,6-dichloro-
2-isocyanatopyrimidine 5 (0.005 mol), and 1,2-dichloroethane (15 mL) were added. The
resulting mixture was stirred at ambient temperature about 15 min, and then evaporated.
The residue was chromatographed on silica gel using acetone–petroleum ether (1:2) as the
eluent to afford the pure title compounds 6a–p as solid in 61%–81% yields.
O,O-Dimethyl 1-((4,6-dichloropyrimidin-2-yl)carbamyloxy)methylphosp
1
honates (6a). White solid: H-NMR (CDCl3, 200 MHz): δ = 3.83 (d, 6H, 2OCH3,
J = 7.0 Hz), 4.55 (d, 2H, OCH2P, J = 8.4 Hz), 4.99 (s, 1H, Ar-H), 9.48 (s, 1H, NH); 31P-
NMR (CDCl3, 81 MHz): δ = 21.6; IR (υ/cm−1): 3447 (N H), 3002 (Ar-H), 1764 (C O),
1560, 1512, 1462 (C C), 1230 (P O), 1185 (C O), 1039 (P O C); Anal. Calcd. for
C8H10Cl2N3O5P: C, 29.19; H, 3.03; N, 12.02. Found: C, 30.07; H, 3.24; N, 11.97.
O,O-Dimethyl 1-((4,6-dichloropyrimidin-2-yl)carbamyloxy)ethylphospho
nates (6b). White solid: 1H-NMR (CDCl3, 200 MHz): δ = 1.51–1.55 (m, 3H, CH3), δ =
3.84 (d, 6H, 2OCH3, J = 3.4 Hz), 5.30–5.32 (m, 1H, -OCHP), 7.27 (s, 1H, Ar–H), 8.70 (s,
1H, NH); 13C-NMR (CDCl3, 50 MHz): δ = 15.7, 54.0, 54.5, 54.6, 54.7, 64.7, 68.2, 116.1,

816
L. XU ET AL.
150.6, 150.8, 157.8, 162.9; 31P NMR (CDCl3, 81 MHz): δ = 23.6; IR (υ/cm−1): 3344
(N H), 3030 (Ar–H), 1765 (C O), 1622, 1582, 1558 (C C), 1245 (P O), 1181 (C-O),
1037 (P O C); Anal. Calcd. for C9H12Cl2N3O5P: C, 31.39; H, 3.48; N, 12.20. Found: C,
31.72; H, 3.54; N, 11.65.
O,O-Dimethyl 1-((4,6-dichloropyrimidin-2-yl)carbamyloxy)propylphosph
1
onates (6c). White solid: H-NMR (CDCl3, 200 MHz): δ = 1.23–1.30 (m, 3H, CH3),
2.16–2.31 (m, 2H, CH2), 3.83 (d, 6H, 2OCH3, J = 3.6 Hz), 5.24 (d, 2H, OCHP, J =
4.0 Hz), 7.12 (s, 1H, Ar–H), 9.05 (s, 1H, NH); 31P-NMR (CDCl3, 81 MHz): δ = 23.2;
IR (υ/cm−1): 3440 (N H), 3108 (Ar–H), 1755 (C O), 1546, 1509 (C C), 1218 (P O),
1180 (C O), 1044 (P O C); Anal. Calcd. for C10H14Cl2N3O5P: C, 33.51; H, 3.91; N,
11.73. Found: C, 33.11; H, 3.79; N, 12.18.
O,O-Dimethyl 1-((4,6-dichloropyrimidin-2-yl)carbamyloxy)pentylphosph
1
onates (6d). White solid: H-NMR (CDCl3, 200 MHz): δ = 0.85–0.89 (m, 3H, CH3),
1.36–1.40 (m, 4H, 2CH2), 1.87–1.90 (m, 2H, CH2), 3.84 (d, 6H, 2OCH3, J = 4.8 Hz),
5.28 (d, 1H, OCHP, J = 5.6 Hz), 7.30 (s, 1H, Ar–H), 9.35 (s, 1H, NH); 31P NMR (CDCl3,
81 MHz): δ = 23.4; IR (υ/cm−1): 3310 (N H), 3020 (Ar–H), 1769 (C O), 1553, 1511
(C C), 1216 (P O), 1182 (C O), 1032 (P O C); Anal. Calcd. for C12H18Cl2N3O5P:
C, 37.30; H, 4.60; N, 10.08. Found: C, 37.45; H, 4.48; N, 9.77.
O,O-Dimethyl 1-((4,6-dichloropyrimidin-2-yl)carbamyloxy)-1-(furan-2-yl)
methylphosphonates (6e). White solid: 1H-NMR (CDCl3, 200 MHz): δ = 3.86 (d, 6H,
2OCH3, J = 9,6 Hz), 6.39 (d, H, OCHP, J = 15.8 Hz), 7.05–7.47 (m, 4H, Ar–H), 8.65 (s,
1H, NH); 31P-NMR (CDCl3, 81 MHz): δ = 16.7; IR (υ/cm−1): 3409 (N H), 3034 (Ar–H),
1769 (C O), 1571, 1552, 1509 (C C), 1218 (P O), 1178 (C O), 1033 (P O C); Anal.
Calcd. for C12H12Cl2N3O6P: C, 33.51; H, 3.91; N, 11.73. Found: C, 33.11; H, 3.79; N,
12.18.
O,O-Dimethyl 1-((4,6-dichloropyrimidin-2-yl)carbamyloxy)-1-(phenyl)me
1
thylphosphonates (6f). White solid: H-NMR (CDCl3, 200 MHz): δ = 3.73 (d, 6H,
2OCH3, J = 10.8 Hz), 6.22 (d, 1H, OCHP, J = 14.0 Hz), 7.32–7.60 (m, 6H, Ar–H),
9.90 (s, 1H, NH); 31P NMR (CDCl3, 81 MHz): δ = 20.1; IR (υ/cm−1): 3432 (N H),
3036 (Ar–H), 1772 (C O), 1554, 1510, 1454 (C C), 1215 (P O), 1171 (C O), 1052
(P O C); Anal. Calcd. for C14H14Cl2N3O5P: C, 41.37; H, 3.44; N, 10.34. Found: C,
41.03; H, 3.81; N, 10.30. MS (m/z,%): 405 (M+ 7.90), 216 (57.60), 191 (55.00), 190
(56.50), 110 (100.00), 105 (54.00), 91 (9.05), 77 (54.45).
O,O-Dimethyl 1-((4,6-dichloropyrimidin-2-yl)carbamyloxy)-1-(2-chlorph
enyl)methylphosphonates (6g). White solid: 1H-NMR (CDCl3, 200 MHz): δ = 3.72
(d, 6H, 2OCH3, J = 11.0 Hz), 6.73 (d, 1H, OCHP, J = 14.2 Hz), 7.22–7.77 (m, 5H, Ar–H),
9.90 (s, 1H, NH); 31P-NMR (CDCl3, 81 MHz): δ = 19.1; IR (υ/cm−1): 3434 (N H),
3037, 3004 (Ar–H), 1762 (C O), 1579, 1552, 1515 (C C), 1219 (P O), 1191 (C O),
1054 (P O C); Anal. Calcd. for C14H13Cl3N3O5P: C, 38.18; H, 2.95; N, 9.54. Found: C,
38.59; H, 3.13; N, 9.01.
O,O-Dimethyl 1-((4,6-dichloropyrimidin-2-yl)carbamyloxy)-1-(4-chlorop
1
henyl) methylphosphonates (6h). White solid: H-NMR (CDCl3, 200 MHz): δ =
3.89 (d, 6H, 2OCH3, J = 9.2 Hz), 6.81 (d, 1H, OCHP, J = 14.0 Hz), 7.15–7.39 (m, 5H,
Ar–H), 10.35 (s, 1H, NH); 31P-NMR (CDCl3, 81 MHz): δ = 19.6; IR (υ/cm−1): 3430
(N H), 3032 (Ar–H), 1781 (C O), 1581, 1555, 1511 (C C), 1213 (P O), 1172 (C O),
1039 (P O C); Anal. Calcd. for C14H13Cl3N3O5P: C, 38.18; H, 2.95; N, 9.54. Found: C,
38.40; H, 2.94; N, 9.52.

O,O-DIALKYL 1-((4,6-DICHLOROPYRIMIDIN-2-YL)CARBAMYLOXY)ALKYLPHOSPHONATES 817
O,O-Dimethyl 1-((4,6-dichloropyrimidin-2-yl)carbamyloxy)-1-(4-nitroph
1
enyl) methylphosphonates (6i). White solid: H-NMR (CDCl3, 200 MHz): δ =
3.86 (d, 6H, 2OCH3, J = 11.0 Hz), 6.23 (d, 1H, OCHP, J = 15.2 Hz), 7.30–7.55 (m,
5H, Ar–H), 9.90 (s, 1H, NH); 31P-NMR (CDCl3, 81 MHz): δ = 18.5; IR (υ/cm−1): 3426
(N H), 3041 (Ar–H), 1764 (C O), 1608, 1581, 1554 (C C), 1216 (P O), 1184 (C O),
1040 (P O C); Anal. Calcd. for C14H13Cl2N4O7P: C, 37.25; H, 2.88; N, 12.41. Found:
C, 37.12; H, 2.94; N, 12.08.
O,O-Diethyl 1-((4,6-dichloropyrimidin-2-yl)carbamyloxy)ethylphosphon
ates (6j). White solid: 1H-NMR (CDCl3, 200 MHz): δ = 1.65 (m, 3H, CH3), 1.44–1.48
(m, 6H, 2CH3), 4.27–4.30 (m, 4H, 2OCH2), 5.43–5.45 (m, 1H, OCHP), 7.06 (s, 1H, Ar–H),
10.23 (s, 1H, NH); 31P-NMR (CDCl3, 81 MHz): δ = 21.5; IR (υ/cm−1): 3350 (N H), 3010
(Ar–H), 1767 (C O), 1612, 1580, 1556 (C C), 1216 (P O), 1182 (C-O), 1050 (P O C);
Anal. Calcd. for C11H16Cl2N3O5P: C, 35.48; H, 4.30; N, 11.29. Found: C, 35.41; H, 4.34;
N, 10.81.
O,O-Diethyl 1-((4,6-dichloropyrimidin-2-yl)carbamyloxy)-1-(phenyl)met
hylphosphonates (6k). White solid: 1H-NMR (CDCl3, 200 MHz): δ = 1.15–1.17 (m,
6H, 2CH3), 4.15–4.17 (m, 4H, 2OCH2), 6.18 (d, 1H, OCHP, J = 15.2 Hz), 7.38–7.61 (m,
6H, Ar–H), 9.80 (s, 1H, NH); 31P-NMR (CDCl3, 81 MHz): δ = 18.1; IR (υ/cm−1): 3416
(N H), 3026 (Ar–H), 1774 (C O), 1577, 1555, 1508 (C C), 1216 (P O), 1172 (C O),
1047 (P O C); Anal. Calcd. for C16H18Cl2N3O5P: C, 44.23; H, 4.14; N, 9.67. Found: C,
44.36; H, 4.17; N, 9.56.
O,O-Diethyl 1-((4,6-dichloropyrimidin-2-yl)carbamyloxy)-1-(2-chlorophe
1
nyl)methylphosphonates (6l). White solid: H-NMR (CDCl3, 200 MHz): δ = δ =
1.15–1.19 (m, 6H, 2CH3), 4.15–4.17 (m, 4H, 2OCH2), 5.60 (d, 1H, OCHP, J = 14.2 Hz),
7.22–7.78 (m, 5H, Ar–H), 9.40 (s, 1H, NH); 31P NMR (CDCl3, 81 MHz): δ = 21.2; IR
(υ/cm−1): 3422 (N H), 3030 (Ar–H), 1772 (C O), 1577, 1551, 1476 (C C), 1216 (P O),
1177 (C O), 1051 (P O C); Anal. Calcd. for C16H17Cl3N3O5P: C, 41.02; H, 3.62; N,
9.09. Found: C, 40.82; H, 3.58; N, 8.57.
O,O-Diethyl 1-((4,6-dichloropyrimidin-2-yl)carbamyloxy)-1-(4-chlorophe
1
nyl)methylphosphonates (6m). White solid: H-NMR (CDCl3, 200 MHz): δ =
1.18–1.21 (m, 6H, 2CH3), 4.24–4.28 (m, 4H, 2OCH2), 6.14 (d, 1H, OCHP, J = 14.2 Hz),
7.28–7.57 (m, 5H, Ar–H), 9.90 (s, 1H, NH); 31P-NMR (CDCl3, 81 MHz): δ = 17.0; IR
(υ/cm−1): 3321 (N H), 3029 (Ar–H), 1781 (C O), 1575, 1552, 1509 (C C), 1216 (P O),
1165 (C O), 1051 (P O C); Anal. Calcd. for C16H17Cl3N3O5P: C, 41.02; H, 3.62; N,
9.09. Found: C, 41.07; H, 3.67; N, 8.54.
O,O-Diisopropyl 1-((4,6-dichloropyrimidin-2-yl)carbamyloxy)ethylphosp
honates (6n). White solid: 1H-NMR (CDCl3, 200 MHz): δ = 1.06–1.65 (m, 15H, 5CH3),
4.80–4.87 (m, 2H, 2CH), 5.18–5.21 (m, 1H, OCHP), 7.30 (s, 1H, Ar–H), 9.70 (s, 1H, NH);
31P-NMR (CDCl3, 81 MHz): δ = 19.4; IR (υ/cm−1): 3310 (N H), 3022 (Ar–H), 1768
(C O), 1576, 1546, 1507 (C C), 1212 (P O), 1180 (C O), 1039 (P O C); Anal.
Calcd. for C13H20Cl2N3O5P: C, 39.02; H, 5.02; N, 10.50. Found: C, 39.07; H, 4.87; N,
10.33.
O,O-Diisopropyl 1-((4,6-dichloropyrimidin-2-yl)carbamyloxy)-1-(phenyl)
methylphosphonates (6o). White solid: 1H-NMR (CDCl3, 200 MHz): δ = 1.31–1.41
(m, 12H, 4CH3), 4.78–4.98 (m, 2H, 2CH), 6.11 (d, 1H, OCHP, J = 14.2 Hz), 7.27–7.64 (m,
6H, Ar–H), 10.10 (s, 1H, NH); 31P NMR (CDCl3, 81 MHz): δ = 15.7; IR (υ/cm−1): 3426
(N H), 3026 (Ar–H), 1772 (C O), 1576, 1553, 1455 (C C), 1217 (P O), 1172 (C O),

818
L. XU ET AL.
1073 (P O C); Anal. Calcd. for C18H22Cl2N3O5P: C, 46.77; H, 4.80; N, 9.09. Found: C,
46.75; H, 4.76; N, 8.57.
O,O-Diisopropyl 1-((4,6-dichloropyrimidin-2-yl)carbamyloxy)-1-(furan-2-
yl)methylphosphonates (6p). White solid: 1H-NMR (CDCl3, 200 MHz): δ =
1.01–1.13 (m, 12H, 4CH3), 4.89–5.06 (m, 2H, 2CH), 6.21 (d, 1H, OCHP, J = 14.2 Hz),
6.68–7.28 (m, 4H, Ar–H), 9.90 (s, 1H, NH); 31P-NMR (CDCl3, 81 MHz): δ = 13.3;
IR (υ/cm−1): 3406 (N H), 3022 (Ar–H), 1774 (C O), 1578, 1551, 1509 (C C), 1215
(P O), 1173 (C O), 1074 (P O C); Anal. Calcd. for C16H20Cl2N3O6P: C, 42.49; H,
4.46; N, 9.29. Found: C, 42.44; H, 4.72; N, 8.90.
FUNDING
This work was supported by the National Basic Research Program of China
(2010CB126100), the National Key Technologies R & D Program of China (No.
2011BAE06B03), and the National Natural Science Foundation of China (No. 21172090).
The research was supported in part by the PCSIRT (No. IRT0953).
SUPPLEMENTAL MATERIAL
Supplementary data of this article can be accessed on the publisher’s website,
www.tandfonline.com/gpss
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