Synthesis and herbicidal activity of α-[2-(fluoro-substituted phenoxy)propionyloxy] alkyl phosphonates

Article abstract of DOI:10.1080/10426500701807566

Eight of novel fluoro-substituted phosphonate derivatives were synthesized and the preliminary bioassay indicated that these compounds exhibited herbicidal activities. Copyright Taylor & Francis Group, LLC.

Full text of DOI:10.1080/10426500701807566

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Phosphorus, Sulfur, and Silicon
and the Related Elements
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Synthesis and Herbicidal
Activity of α-[2-
(Fluoro-Substituted
Phenoxy)Propionyloxy] Alkyl
Phosphonates
Yan-Jun Li a & Hong-Wu He a
a Key Laboratory of Pesticide and Chemical Biology
of Ministry of Education , Central China Normal
University , Wuhan, P. R. China
Published online: 20 Jun 2008.
To cite this article: Yan-Jun Li & Hong-Wu He (2008) Synthesis and Herbicidal
Activity of α-[2-(Fluoro-Substituted Phenoxy)Propionyloxy] Alkyl Phosphonates,
Phosphorus, Sulfur, and Silicon and the Related Elements, 183:2-3, 712-713, DOI:
10.1080/10426500701807566
To link to this article: http://dx.doi.org/10.1080/10426500701807566
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Phosphorus, Sulfur, and Silicon, 183:712–713, 2008
Copyright © Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426500701807566
Synthesis and Herbicidal Activity
of α-[2-(Fluoro-Substituted Phenoxy)Propionyloxy]
Alkyl Phosphonates
Yan-Jun Li and Hong-Wu He
Key Laboratory of Pesticide and Chemical Biology of Ministry
of Education, Central China Normal University, Wuhan,
P. R. China
Eight of novel fluoro-substituted phosphonate derivatives were synthesized and
the preliminary bioassay indicated that these compounds exhibited herbicidal
activities.
Keywords Fluoro-substituted; phosphonate; synthesis
The title compound was synthesized by the reaction of O,O-dimethyl
1-hydroxyalkylphosphonate and 2-(fluoro-substituted phenoxy) propi-
onyl chloride according to a literature procedure.1,2 O,O-dimethyl 1-
hydroxyalkylphosphonate could be prepared by the reaction of dimethyl
phosphite and several types of aldehydes using potassium fluoride and
alumina (mass ratio was 1:1) as a catalyst with a yield of 56%–88%.3−5
Adding triethylamine as catalyst and trap of acid, the synthesis of
the title compounds could be completed with an isolated yield of 20%–
70%.
1
All eight compounds were confirmed by H NMR, IR, MS spectra
and elemental analysis. The results of preliminary bioassay indicated
that the title compounds exhibited significant herbicidal activities. It is
worthy to note that the introduction of fluorine moiety to phosphonate’s
structure was useful for the improvement of 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
712

Alkyl Phosphonates
713
X
Y
X
BrCH(CH3)COOEt
OH
OCHCOOEt
CH3
K2CO3
Y
X
1) SOCl2
1) NaOH
2) HCl
OCHCOOH
(CH3O)2POCH(OH)R
II
2
Y
CH3
I
O
O
X
Y
H3CO
H3CO
PCHOCCHO
CH3
III
4-CH3-Ph, 4-F-Ph
R
R=CH3
,
CCl3
,
X, Y=2-F-H, 2-Cl-4-F
REFERENCES
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[2] H. W. He, Chin. J. Org. Chem., 23, 155 (2003).
[3] B. J. Lowis, T. Laurent, and Tessier Jean. EP376819, 1990.
[4] B. Springs and P. Healbe. J. Org. Chem., 14, 1165 (1976).
[5] F. B. Francoise and L. Maryvonne, Tetrahedron. Lett., 27, 3515 (1986).