Synthesis, crystal structure, and bioactivities of dimethyl[(3,7- dichloroquinolin-8-yl carbonyloxy)alkyl] phosphonate

Article abstract of DOI:10.1080/10426500701807582

Fourteen of phosphonates containing quinoline were synthesized and the preliminary bioassay indicated that these compounds exhibited a little better fungicidal and lower herbicidal activities than the starting compound Quinclorac. Copyright Taylor & Francis Group, LLC.

Full text of DOI:10.1080/10426500701807582

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Phosphorus, Sulfur, and Silicon
and the Related Elements
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Synthesis, Crystal
Structure, and Bioactivities
of Dimethyl[(3,7-
Dichloroquinolin-8-
yl Carbonyloxy)Alkyl]
Phosphonate
Ying Liang a , Ya-Zhou Wang a & Hong-Wu He a
a Key Laboratory of Pesticide and Chemical Biology
of Ministry of Education , Central China Normal
University , Wuhan, People's Republic of China
Published online: 20 Jun 2008.
To cite this article: Ying Liang , Ya-Zhou Wang & Hong-Wu He (2008) Synthesis,
Crystal Structure, and Bioactivities of Dimethyl[(3,7-Dichloroquinolin-8-yl
Carbonyloxy)Alkyl] Phosphonate, Phosphorus, Sulfur, and Silicon and the Related
Elements, 183:2-3, 714-715, DOI: 10.1080/10426500701807582
To link to this article: http://dx.doi.org/10.1080/10426500701807582
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Phosphorus, Sulfur, and Silicon, 183:714–715, 2008
Copyright © Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426500701807582
Synthesis, Crystal Structure, and Bioactivities
of Dimethyl[(3,7-Dichloroquinolin-8-yl
Carbonyloxy)Alkyl] Phosphonate
Ying Liang, Ya-Zhou Wang, and Hong-Wu He∗
Key Laboratory of Pesticide and Chemical Biology of Ministry
of Education, Central China Normal University, Wuhan, People’s
Republic of China
Fourteen of phosphonates containing quinoline were synthesized and the prelimi-
nary bioassay indicated that these compounds exhibited a little better fungicidal
and lower herbicidal activities than the starting compound Quinclorac.
Keywords Bioactivities; phosphonate; quinoline; synthesis
3,7-Dichloroquinoline-8-carbonyl chloride was reacted with O,O-
dimethyl-1-hydroxyalkylphosphonates1,2 to form 3,7-dichloroquinolin-
8-yl carbonyloxyalkylphosphonate. The preparation of title compounds
could be completed in anhydrous solvent at 2–15◦C for 2–5 h good yields
(60%–80%) by adding triethylamine (1.2 equivalent) as catalyst and
1
trap of acid. All 14 compounds were confirmed by H NMR, IR, MS
spectra and elemental analysis, and one was examined by the single
This work was supported by the National Basic Research Program of China
(No: 2003CB114400) and the National Natural Science Foundation of China
(No: 20372023, 20772042).
∗Now at Hubei Biopesticide Engineering Research Center, Hubei Academy of Agri-
cultural Science, Wuhan 430064, People’s Republic of China.
Address correspondence to Hong-Wu He, Key Laboratory of Pesticide and Chemi-
cal Biology of Ministry of Education, Central China Normal University, Wuhan 430079,
People’s Republic of China. E-mail: hel208@mail.ccnu.edu.cn
714

Dimethyl[(3,7-Dichloroquinolin-8-yl Carbonyloxy)Alkyl] Phosphonate
715
crystal X-ray diffraction.3 The results of preliminary bioassay indicated
that the title compounds (R=H, alkyl, Ph, substituted Ph, furfuryl) ex-
hibited a little better fungicidal activities and lower herbicidal activities
than the starting compound Quinciorac, a commercialized herbicide.
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