Synthesis of novel bicycli caged phosphate derivatives

Article abstract of DOI:10.1080/10426500701807491

A series of bicycli caged phosphates were synthesized, and biological activity test showed that the title compounds exhibited moderate herbicidal activity. Copyright Taylor & Francis Group, LLC.

Full text of DOI:10.1080/10426500701807491

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Phosphorus, Sulfur, and Silicon
and the Related Elements
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Synthesis of Novel Bicycli
Caged Phosphate Derivatives
a
a
Wen-Yan Mo & Hong-Wu He
a
Key Laboratory of Pesticide and Chemical Biology
of Ministry of Education, Central China Normal
University, Wuhan, P. R. China
Version of record first published: 20 Jun 2008.
To cite this article: Wen-Yan Mo & Hong-Wu He (2008): Synthesis of Novel Bicycli
Caged Phosphate Derivatives, Phosphorus, Sulfur, and Silicon and the Related
Elements, 183:2-3, 699-700
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Phosphorus, Sulfur, and Silicon, 183:699–700, 2008
Copyright © Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426500701807491
Synthesis of Novel Bicycli Caged Phosphate Derivatives
Wen-Yan Mo and Hong-Wu He
Key Laboratory of Pesticide and Chemical Biology of Ministry
of Education, Central China Normal University, Wuhan, P. R. China
A series of bicycli caged phosphates were synthesized, and biological activity test
showed that the title compounds exhibited moderate herbicidal activity.
Keywords Bicycli caged phosphates; herbicidal activity; synthesis
The symmetrical caged bicyclic phosphate 2 has been synthesized
by Verkade many years ago,1 of which the derivatives possessed
good biological activities, and were particularly useful as herbicides
2
−4
and fungicides.
Herein we synthesized a series of novel bicy-
cle caged phosphate derivatives containing α-hydroxy alkyl phos-
phonates. The precursors of α-hydroxy alkyl phosphonates 1 were
generated by dimethylphosphite’s addiction toward aldehydes with
◦
ice bath (0–5 C) using triethylamine or KF/Al2O3 (quantity ratio is
1:1) as catalyst. Pentaerythritol was reacted with POCl3 and led to
preferable formation (87–95%) of 1-hydroxymethyl-4-phospha-3,5,8-
trioxabicyclo[2,2,2]octane 2, which afforded the corresponding acid 3
5
−8
via oxidation by nitric acid using NH4VO3 as catalyst.
And 3 was
easily acylated and reacted with α-hydroxyalkyl phosphonates 1 to
give title compounds 4 with moderate to good yields. The preliminary
bioassay indicated that the compounds exhibited moderate herbicidal
activity.
Financial support by National Basic Research Program of China (2003CB114400) and
NNSF of China (20372023, 20772042).
Address correspondence to Hongwu He, Key Laboratory of Pesticide and Chemical
Biology of Ministry of Education, Central China Normal University, Wuhan 430079, P. R.
China. E-mail: hel208@mail.ccnu.edu.cn
699

7
00
W.-Y. Mo and H.-W. He
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