Synthesis and herbicidal activities of lithium or potassium hydrogen 1-(substituted phenoxyacetoxy)alkylphosphonates

Article abstract of DOI:10.1080/10426507.2013.797415

A series of lithium or potassium hydrogen 1-(substituted phenoxyacetoxy)alkylphosphonates were designed and synthesized. All the title compounds were identified by IR, ¹H NMR, and ³¹P NMR, some of them were further analyzed by MS and elemental analyses. The test for herbicidal activity indicated that most of the phosphonates (8) possessed excellent postemergence herbicidal activities against broadleaf weeds. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.

Full text of DOI:10.1080/10426507.2013.797415

This article was downloaded by: [Uppsala universitetsbibliotek]
On: 05 October 2014, At: 21:54
Publisher: Taylor & Francis
Informa Ltd Registered in England and Wales Registered Number: 1072954 Registered
office: Mortimer House, 37-41 Mortimer Street, London W1T 3JH, UK
Phosphorus, Sulfur, and Silicon and the
Related Elements
Publication details, including instructions for authors and
subscription information:
http://www.tandfonline.com/loi/gpss20
Synthesis and Herbicidal
Activities of Lithium or Potassium
Hydrogen 1-(Substituted
Phenoxyacetoxy)Alkylphosphonates
Hao Peng a , Qingwu Long a , Xiaoyan Deng a & Hongwu He a
a The Key Laboratory of Pesticide & Chemical Biology, Ministry
of Education, and College of Chemistry, Central China Normal
University , Wuhan , 430079 , P.R. China
Accepted author version posted online: 26 Jul 2013.Published
online: 03 Oct 2013.
To cite this article: Hao Peng , Qingwu Long , Xiaoyan Deng & Hongwu He (2013)
Synthesis and Herbicidal Activities of Lithium or Potassium Hydrogen 1-(Substituted
Phenoxyacetoxy)Alkylphosphonates, Phosphorus, Sulfur, and Silicon and the Related Elements, 188:12,
1868-1874, DOI: 10.1080/10426507.2013.797415
To link to this article: http://dx.doi.org/10.1080/10426507.2013.797415
PLEASE SCROLL DOWN FOR ARTICLE
Taylor & Francis makes every effort to ensure the accuracy of all the information (the
“Content”) contained in the publications on our platform. However, Taylor & Francis,
our agents, and our licensors make no representations or warranties whatsoever as to
the accuracy, completeness, or suitability for any purpose of the Content. Any opinions
and views expressed in this publication are the opinions and views of the authors,
and are not the views of or endorsed by Taylor & Francis. The accuracy of the Content
should not be relied upon and should be independently verified with primary sources
of information. Taylor and Francis shall not be liable for any losses, actions, claims,
proceedings, demands, costs, expenses, damages, and other liabilities whatsoever or
howsoever caused arising directly or indirectly in connection with, in relation to or arising
out of the use of the Content.
This article may be used for research, teaching, and private study purposes. Any
substantial or systematic reproduction, redistribution, reselling, loan, sub-licensing,
systematic supply, or distribution in any form to anyone is expressly forbidden. Terms &

Conditions of access and use can be found at http://www.tandfonline.com/page/terms-
and-conditions

Phosphorus, Sulfur, and Silicon, 188:1868–1874, 2013
Copyright ꢀC Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426507.2013.797415
SYNTHESIS AND HERBICIDAL ACTIVITIES OF LITHIUM
OR POTASSIUM HYDROGEN 1-(SUBSTITUTED
PHENOXYACETOXY)ALKYLPHOSPHONATES
Hao Peng, Qingwu Long, Xiaoyan Deng, and Hongwu He
The Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, and
College of Chemistry, Central China Normal University, Wuhan 430079, P.R. China
GRAPHICAL ABSTRACT
Abstract
A series of lithium or potassium hydrogen 1-(substituted phenoxyace-
toxy)alkylphosphonates were designed and synthesized. All the title compounds were identified
by IR, 1H NMR, and 31P NMR, some of them were further analyzed by MS and elemental
analyses. The test for herbicidal activity indicated that most of the phosphonates (8) possessed
excellent postemergence herbicidal activities against broadleaf weeds.
Supplemental materials are available for this article. Go to the publisher’s online edition of
Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.
Keywords Synthesis; herbicidal activity; phosphonate
INTRODUCTION
α-Substituted alkylphosphonate derivatives have received considerable attention in
medicine and pesticide chemistry due to their biological activities over the past two
decades.1–5 Especially, α-(substituted phenoxyacetoxy)alkylphosphonates, as potent pyru-
vate dehydrogenase complex inhibitors,6,7 possess notable herbicidal activities.8 Based on
Received 10 December 2012; accepted 16 April 2013.
This work was supported by the National Basic Research Program of China (No. 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).
Address correspondence to Hongwu He, College of Chemistry, Central China Normal University, 152 Luoyu
Road, Wuhan 430079, P.R., China. E-mail: he1208@mail.ccnu.edu.cn
1868

SYNTHESIS AND HERBICIDAL ACTIVITIES OF PHOSPHONATE DERIVATIVES
1869
the bioisosterism, their phosphonic acids were assumed to have better herbicidal activity,
because phosphonic acid is more analogous to the pyruvic acid, which acts as the substrate
of pyruvate dehydrogenase complex.9,10 However, as strong acids, these phosphonic acids
themselves would lead to the cleavage of carboxylate ester group in the structures. In our pre-
vious work, a series of sodium hydrogen 1-(substituted phenoxyacetoxy)alkylphosphonates
were synthesized, which are almost neutral salts with higher stability than the corresponding
phosphonic acids. Most of these compounds showed excellent postemergence herbicidal
activities against broadleaf weeds, controlling more than 90% of rape and amaranth at
150 g/ha. On the other hand, lithium and potassium are often used for the isoelectronic re-
placement of sodium ions in medical molecules to obtain higher bioactivity and safety,10,11
which encouraged us to replace the sodium with the lithium or potassium and further study
the relationship of structure–herbicidal activity. Herein, we reported the synthesis of 26
new lithium or potassium hydrogen 1-(substituted phenoxyacetoxy)alkylphosphonates and
evaluation for their herbicidal activities.
RESULTS AND DISCUSSION
Syntheses
The multistep procedure for the synthesis of the title phosphonates 8 is out-
lined in Scheme 1. The methods for the synthesis of substituted phenoxyacetyl chlo-
ride 2, dimethyl 1-hydroxyalkylphosphonates 4, and dimethyl 1-(substituted phenoxy-
acetoxy)alkylphosphonates 5 were adopted, according to the previous work reported in
our group.12–14 The phosphonates 5 reacted with chlorotrimethylsilane in acetonitrile
using sodium iodide as catalyst to provide bis(trimethylsilyl) 1-(substituted phenoxy-
acetoxy)alkylphosphonates 6, which was further transformed to 1-(substituted phenoxy-
acetoxy)alkylphosphonic acids 7 by reaction with methanol. The title phosphonates 8
were then obtained by the reaction with lithium hydroxide or potassium carbonate (Table 1).
1
The structures of 8a–8z were confirmed by comprehensive IR, H NMR, 31P NMR,
elemental analysis, and 8a, 8h, 8n, and 8u were further identified via mass spectrum
(MS).
The infra red (IR spectra of compounds 8a–8z showed normal stretching ab-
sorption bands indicating the existence of C C (∼1620, ∼1450 cm−1), C O C
(1080–1200 cm−1), and P C (740–750 cm−1). A sharp and weak band at 2950–3100 cm−1
accounted for the C–H stretching of the benzene ring. The C–H stretching of alkyl
appeared at 2860–2950 cm−1. A strong absorption near 1720–1760 cm−1 was iden-
1
tified for the absorption C O. In the HNMR spectra of the title compounds 8a–8z,
the chemical shifts of aromatic protons appeared at 6.8–7.8 ppm. As for compounds
with aliphatic groups as R, the proton signal corresponding to methenyl attached
to the P atom displayed multiplets at 5.00–5.23; as for the compounds with aro-
matic groups as R, the proton signal appears at 5.76–6.31 as doublets, due to the
coupling with phosphorus.31P NMR chemical shifts of compounds 8a–8z appeared
as a singlet at δ 15.5–16.2 ppm. Their chemical shifts were moved upfield by
approximately 7–8 ppm, compared with that of the corresponding O,O-dimethyl
phosphonates at ∼23 ppm, whereas the chemical shifts of compounds 8a–8z moved
downfield by approximately 3–4 ppm, compared with the 2-methylpropan-2-aminium
phosphonates.15

1870
H. PENG ET AL.
Table 1 Structure and physicochemical data of title compounds 8a–8z
Compd.
X
Y
M
R
Appearance
mp/◦C
Yield/%
8a
8b
8c
8d
8e
8f
8g
8h
8i
8j
8k
8l
8m
8n
8o
8p
8q
8r
8s
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Li
Li
Li
Li
Li
Li
Li
Li
Li
Li
Li
Li
Li
K
K
K
K
K
K
K
K
K
CH3
C2H5
n-C3H7
i-C3H7
n-C4H9
phenyl
thien-2-yl White solid
CH3
C2H5
n-C3H7
i-C3H7
n-C4H9
phenyl
CH3
White solid 222–224
White solid 226–228
White solid 219–221
White solid 207–209
White solid 188–190
White solid 149–150
84
77
82
83
84
85
47
90
87
82
92
89
85
93
93
84
87
84
86
65
91
85
81
95
90
82
Cl
Cl
>250
CH3
CH3
CH3
CH3
CH3
CH3
Cl
Cl
Cl
Cl
Cl
White solid 175–176
White solid 203–205
White solid 236–238
White solid 203–205
White solid 208–210
White solid 152–153
White solid 138–140
C2H5
White solid
99–100
n-C3H7
i-C3H7
n-C4H9
phenyl
White solid 103–104
White solid 107–108
White solid 139–140
White solid 141–142
Cl
Cl
8t
thien-2-yl White solid 144–145
CH3
C2H5
n-C3H7
i-C3H7
n-C4H9
phenyl
8u
8v
8w
8x
8y
8z
CH3
CH3
CH3
CH3
CH3
CH3
White solid 154–155
White solid 104–105
White solid 113–114
White solid 102–103
White solid 118–120
White solid 109–110
K
K
K
K
Herbicidal Activities
The preliminary herbicidal activities of title compounds against the roots and stems
of Brassica napus L.(rape) and Echinochloa crusgalli Beava (barnyard grass) were tested
at the dosage of 10 and 100 μg/g, respectively. The results showed that some of the
synthesized compounds displayed notable herbicidal activities against the tested plants,
and they displayed higher inhibitory activities against the growth of the root than that of the
stem. For example, 8a–8z showed 96%–99% inhibitory rate against the root of B. napus L.
at the dosage of 10 μg/g, but only 75%–92% inhibitory rate against the stem of B. napus
L. at the same dosage. The inhibitory activities of title compounds against dicotyledon
were higher than those against monocotyledon. For example, 8a–8z showed 75%–92%
inhibitory rate against the stem of dicotyledon B. napus L. at the dosage of 10 μg/g, but
they displayed 28%–76% inhibitory effect against the root of monocotyledon E. crusgalli
at the same dosage.
Based on the preliminary bioassays, compounds 8a–8g, 8i, 8k–8l, 8n–8t, 8v,
and 8y were selected for further bioassay for postemergence herbicidal activity on
Echinochloa crusgalli Beava (barnyard grass), Digitaria sanguinalis Scop (ascendant
crabgrass), Brassica napus L. (rape), Amaranthus retroflerus L. (amaranth), Setaria
viridis (green bristlegrass), and Chenopodium serotinum (small goosefoot). And sodium
hydrogen 1-(2,4-dichlorophenoxyacetoxy)ethylphosphonate were selected as a positive
control. It was found that the tested compounds displayed higher herbicidal activities

SYNTHESIS AND HERBICIDAL ACTIVITIES OF PHOSPHONATE DERIVATIVES
1871
against dicotyledonous weeds than monocotyledon, which is agreement with the re-
sults in the preliminary bioassays. The compound 8a showed the best herbicidal activ-
ity against the monocotyledon, and with more than 85% inhibitory rate against all the
tested dicotyledonous weeds, which is better than the corresponding potassium hydro-
gen 1-(2,4-dichlorophenoxyacetoxy)ethylphosphonate 8n and sodium hydrogen 1-(2,4-
dichlorophenoxyacetoxy)ethylphosphonate. As a result, lithium salts showed higher her-
bicidal against the monocotyledons than the corresponding potassium and sodium salts,
especially for the compounds with 2,4-Cl2 as the X and Y groups. However, as for the
dicotyledonous plants, the three kinds of salts showed the comparable herbicidal activity,
which is different to the results observed against the monocotyledons.
Experimental details and the herbicidal activities (Table S 1 and Table S 2) are
presented in the online Supplemental Materials.
CONCLUSIONS
In conclusion, a series of lithium or potassium hydrogen 1-(substituted phenoxy-
acetoxy)alkylphosphonates were synthesized via the key intermediate 1-(substituted
phenoxyacetoxy)alkylphosphonic acids with satisfactory yields. The test for herbicidal
activity indicated that most of the title compounds possessed excellent postemergence
herbicidal activities against broadleaf weeds, and they displayed higher herbicidal activities
against dicotyledonous weeds than monocotyledon. Especially, lithium hydrogen 1-(2,4-
dichlorophenoxyacetoxy)ethylphosphonate 8a showed higher herbicidal activity than the
corresponding potassium hydrogen 1-(2,4-dichlorophenoxyacetoxy)ethylphosphonate 8n
and sodium hydrogen 1-(2,4-dichlorophenoxyacetoxy)ethylphosphonate, which provided
some indications for further studies on structure modification.
EXPERIMENTAL
Mass spectra were measured on API2000LC/MS. Infrared spectra were recorded in
potassium bromide pellets with a Nicolet Avatar 360 Fourier transform infrared (FTIR)
spectrophotometer.1HNMR and 31PNMR spectra were recorded in D2O solution using
sodium 3-(trimethylsilyl)propane-1-sulfonate (DSS) as internal standards with a Varian
Mercury-Plus 400 (400 MHz) spectrometer. Elemental analysis was performed with an
Elementar Vario EL III elementary analyzer. Melting points (mp) were measured with an
1
electrothermal melting point apparatus and are uncorrected. Selected H and 31P NMR
spectra are shown in the online Supplemental Materials (Figures S1–S6).
Synthesis
All of the compounds 1–5 were synthesized according to the methods described in
the literature.16–18 (Scheme 1).
General Procedure for 5
To a solution of dimethyl (1-hydroxyalkyl)phosphonates 4 (10 mmol) and pyridine
(14 mmol) in CH2Cl2 (25 mL), a solution of substituted phenoxyacetyl chloride 2 (10 mmol)
was added in CH2Cl2 (15 mL) dropwise at below 5◦C, and the mixture was stirred for 4 h,
which was monitored by thin layer chromatography (TLC). The oily residue was purified

1872
H. PENG ET AL.
Scheme 1 Synthesis of the title compounds 8.
by flash column chromatography on silica gel with the mixture of acetone/petroleum ether
(v:v 1:4) as eluent to furnish 5.
General Procedure for 6
Under a nitrogen atmosphere and in a dark environment, to a solution of 5 (10 mmol)
and sodium iodide (22 mmol) in acetonitrile (25 mL), trimethylchlorosilane (22 mmol)
was added at 30◦C, then the reaction mixture was stirred for 2 h. The resultant mixture
was purified by flash column chromatography on silica gel with a mixture of petroleum
ether/n-propanol (v:v 3:1) as eluent to furnish 6 as a colorless oil.
General Procedure for 7
To a solution of 6 (10 mmol) in anhydrous methanol (25 mL), the reaction mixture
was stirred for 2–3 h at 30◦C, which was monitored by TLC. The solvent was removed
under reduced pressure followed by column chromatography on silica gel with a mixture
of petroleum ether/n-propanol (v:v 1:3) as eluent to yield 7.

SYNTHESIS AND HERBICIDAL ACTIVITIES OF PHOSPHONATE DERIVATIVES
1873
General Procedure for Compounds (8)
To a solution of 7 (5.5 mmol) in methanol (20 mL) was added lithium hydroxide or
potassium carbonate (5 mmol), and the mixture was stirred at room temperature for 2 h.
Removal of the solvent under reduced pressure gave the crude product as a white solid,
which was recrystallized from acetonitrile to afford 8.
Lithium Hydrogen 1-(2,4-Dichlorophenoxyacetoxy)ethylphosphonate
1
3
3
(8a). White solid, Yield 84%; H NMR (D2O) δ : 1.41 (dd, 3H, JHH = 7.2 Hz, JPH
=
2
14.4 Hz, P CH CH3), 4.90, 4.93 (q, AB system, 2H, JAB = −16.8 Hz, O-CH2-C),
5.00–5.05 (m, 1H, P-CH), 7.00 (d, 1H, Jo = 8.8 Hz, H6-Ph), 7.27 (t, 1H, Jo = 8.8 Hz,
H5-Ph), 7.47 (s, 1H, H3-Ph); 31P NMR (160 MHz, D2O) δ: 15.468; IR ν /cm−1: 3424,
2982, 2938, 1751, 1481, 1440, 1392, 1201, 1108, 1078, 992, 869, 800, 720; ESI-MS(m/z):
positive: 357(M + 23, 22.27%), 341(M + 7, 35.96%), 334(M+, 3.07%), 301(22.38%),
285(100%), 229(65.74%), 85(26.27%); negative: 331(M-7 + 4, 11.17%), 329(M-7+2,
61.63%), 327(M-7, 100%), 283(7.73%), 255(11.48%), 219(5.82%), 165(21.79%),
161(10.64%), 125(32.82%), 121(20.24%), 107(62.16%), 63(61.59%); Elemental Anal.
Calcd. For C10H10Cl2LiO6P: C 35.85, H 3.01; Found C 35.75, H 2.80.
3
3
Lithium Hydrogen 1-(4-Chloro-2-methylphenoxyacetoxy)ethylphosphon
1
3
ate(8h). White solid, Yield 90%; H NMR (D2O) δ : 1.42 (dd, 3H, JHH = 6.8 Hz,
3JPH = 14.8 Hz, P CH CH3), 2.23 (s, 3H, C6H3-CH3), 4.86 (s, 2H, O CH2-C),
5.13∼5.16 (m, 1H, P CH), 6.84 (d, 1H, Jo = 8.8 Hz, H6-Ph), 7.18 (t, 1H, 3Jo
=
3
8.8 Hz, H5-Ph), 7.25 (s, 1H, H3-Ph); 31P NMR (160 MHz, D2O) δ: 15.573; IR ν
/cm−1: 3410, 2957, 2355, 1763, 1651, 1600, 1493, 1441, 1402, 1381, 1298, 1187, 1138,
1074, 998, 922, 882, 801; ESI-MS(m/z): positive: 337(M+23, 40.30%), 320(M-1+7,
70.40%), 315(M+1, 16.42%), 301(12.19%), 285(45.02%), 254(11.44%), 250(12.44%),
237(12.44%), 229(100%), 221(23.38%), 136(31.84%), 85(29.10%); negative: 321(M + 7,
6.85%), 309(M-7 + 2, 28.90%), 307(M-7, 100%), 201(6.04%), 199(21.09%), 165(2.30%),
143(12.35%), 141(36.38%), 125(28.10%), 107(47.09%), 63(68.86%); Elemental Anal.
Calcd. for C11H13ClLiO6P: C 42.00, H 4.17; found C 42.13, H 4.60.
Potassium Hydrogen 1-(2,4-Dichlorophenoxyacetoxy)ethylphosphonate
1
3
3
(8n). White solid, Yield 93%; H NMR (D2O) δ : 1.47 (dd, 3H, JHH = 7.0 Hz, JPH
=
15.4 Hz, P CH CH3), 4.93 (s, 2H, O CH2-C), 5.17–5.23 (m, 1H, P CH), 6.99 (d, 1H,
3Jo = 8.8 Hz, H6-Ph), 7.28 (t, 1H, 3Jo = 8.8 Hz, 4Jm = 2.0 Hz, H5-Ph), 7.49 (d, 1H, 4Jm
= 2.0 Hz, H3-Ph); 31P NMR (160 MHz, D2O) δ: 15.986; IR ν /cm−1: 3423, 2992, 2938,
1754, 1482, 1439, 1391, 1288, 1212, 1084, 924, 870, 801, 720; ESI-MS(m/z): positive:
389(M + 23, 22.74%), 367(M + 1, 19.59%), 317(100%), 301(10.96%), 261(28.93%),
136(22.13%); negative: 331(M-39 + 4, 13.74%), 329(M-39 + 2, 68.27%), 327(M-39,
100%), 283(4.43%), 219(7.33%), 165(19.42%), 161(12.86%), 125(24.46%), 107(44.59%),
63(44.30%); Elemental Anal. Calcd. for C10H10Cl2KO6P: C 32.71, H 2.75; found C 32.41,
H 2.88.
Potassium Hydrogen 1-(4-Chloro-2-methylphenoxyacetoxy)ethylphosp
honate(8u). White solid, Yield 91%; 1H NMR (D2O) δ : 1.42 (dd, 3H, 3JHH = 6.8 Hz, 3JPH
= 15.2 Hz, P CH CH3), 2.24 (s, 3H, C6H3-CH3), 4.86 (s, 2H, O CH2-C), 5.13∼5.16
(m, 1H, P CH), 6.84 (d, 1H, 3Jo = 8.8 Hz, H6-Ph), 7.18 (t, 1H, 3Jo = 8.8 Hz, H5-Ph), 7.26
(s, 1H, H3-Ph); 31P NMR (160 MHz, D2O) δ: 16.002; IR ν /cm−1: 3417, 3218, 2985, 2922,
2275, 1747, 1653, 1493, 1439, 1381, 1338, 1290, 1241, 1191, 1163, 1138, 1077, 1025,
928, 876, 792, 737; ESI-MS(m/z): positive: 369(M + 23, 31.26%), 346(M+, 24.42%),
250(72.34%), 136(17.59%), 60(100%); negative: 309(M-39 + 2, 35.54%), 307(M-7,

1874
H. PENG ET AL.
95.59%), 199(10.90%), 143(7.48%), 141(17.54%), 125(31.88%), 107(66.38%), 63(100%);
Elemental Anal. Calcd. for C11H13ClKO6P: C 38.10, H 3.78; found C 38.41, H 3.75.
The Supplemental Materials contains complete characterization data for all the other
reported compounds.
REFERENCES
1. O’Neal, J. B.; Rosen, H.; Russel, P. B.; Adams, A. C.; Blumenthal, A. J. Med. Pharm. Chem.
1962, 5, 617-626.
2. Makarov, M. V.; Rybalkina, E. Yu.; Ro¨schenthaler, G.-V.; Short, K. W.; Timofeeva, T. V.; Odinets,
I. L. Eur. J. Med. Chem. 2009, 44, 2135-2144.
3. Koh, Y.; Shim, J. H.; Wu, J. Zh.; Zhong, W. D.; Hong, Zh.; Girardet, J. L. J. Med. Chem. 2005,
48, 2867-2875.
4. Finn, J.; Langevine, C.; Birk, I.; Birk, J.; Nickerson, K.; Rodaway, S. Bioorg. Med. Chem. Lett.
1999, 9, 2297-2302.
ˇ
5. Gobec, S.; Plantan, I.; Mravljak, J.; Svajger, U.; Wilson, R. A.; Besra, G. S.; Soares, S. L.;
Appelberg, R.; Kikelj, D. Eur. J. Med. Chem. 2007, 42, 54-63.
6. Wang, T.; He, H. W.; Yuan, J. L. Chin. J. Appl. Chem. 2003, 20, 613-617.
7. Tan, H. L.; Yuan, J. L.; He, H. W.; Wang, T. Chin. J. Chem. Eng. 2005, 6, 4-5.
8. Peng, H.; Wang, T.; Xie, P.; Chen, T.; He, H. W. J. Agric. Food Chem. 2007, 55, 1871-1880.
9. Nemeria, N.; Yan, Y.; Zhang, Z.; Brown, A. M.; Arjunan, P.; Fruey, W.; Guest, J. R.; Jordan, F.
J. Biol. Chem. 2001, 276, 45969-45978.
10. He, H. W.; Wang, T.; Yuan, J. L. J. Organomet. Chem. 2005, 690, 2608-2613.
11. Wang, T.; He, H. W. Phosphorus, Sulfur Silicon Relat. Elem. 2004, 179, 2081-2089.
12. He, H. W.; Chen, T.; Li, Y. J. J. Pestic. Sci. 2007, 32, 42-44.
13. He, H. W.; Wang, J.; Liu, Z. J.; Wan, S. Q.; Lou, A. H. Chin. J. Appl. Chem. 1994, 11, 21-24.
14. He, H. W.; Liu, Z. J. Chin. J. Org. Chem. 2001, 21, 878-883.
15. Gao, L.; Deng, X. Y.; Tan, X. S.; Long, Q. W.; Peng, H.; He, H. W. Phosphorus, Sulfur Silicon
Relat. Elem. 2013, doi: 10.1080/10426507.2012.736101
16. He, H. W.; Yuan, J. L.; Peng, H.; Chen, T. J. Agric. Food Chem. 2011, 59, 4801-4813.
17. Wang, T.; He, H. W. Synth. Commun. 2004, 34, 1415-1423.
18. Chen, T.; Shen, P.; Li, Y. J.; He, H. W. J. Fluorine Chem. 2006, 127, 291-295.