Synthesis and Herbicidal Activity of [alpha]-Amino Phosphonate Derivatives Containing Thiazole and Pyrazole Moieties

A series of novel α-amino phosphonate derivatives containing the thiazole and pyrazole moieties 3 were synthesized by the Mannich-type reaction of substituted pyrazole-aldehyde 1, 2-amino-5-ethoxycarbonyl-4-methyl-thiazole 2, and dialkyl phosphites or triphenyl phosphite in the presence of a Lewis a...

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Published in:Phosphorus, sulfur, and silicon and the related elements sulfur, and silicon and the related elements, 2010-08, Vol.185 (8), p.1746
Main Authors: Yu, Zhi-Hua, Shi, De-Qing
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Shi, De-Qing
description A series of novel α-amino phosphonate derivatives containing the thiazole and pyrazole moieties 3 were synthesized by the Mannich-type reaction of substituted pyrazole-aldehyde 1, 2-amino-5-ethoxycarbonyl-4-methyl-thiazole 2, and dialkyl phosphites or triphenyl phosphite in the presence of a Lewis acid such as magnesium perchlorate as the catalyst under solvent-free conditions. Their structures were clearly confirmed by spectroscopy data (IR, 1H NMR, 31P NMR, MS) and elemental analysis. The results of a preliminary bioassay (in vitro) indicated that some of the title compounds 3 possessed moderate herbicidal activities against dicotyledonous plants (Brassica campestris L) or monocotyledonous plants (Echinochloa crus-galli) at the concerntration of 100 mg/L. 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.
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Their structures were clearly confirmed by spectroscopy data (IR, 1H NMR, 31P NMR, MS) and elemental analysis. The results of a preliminary bioassay (in vitro) indicated that some of the title compounds 3 possessed moderate herbicidal activities against dicotyledonous plants (Brassica campestris L) or monocotyledonous plants (Echinochloa crus-galli) at the concerntration of 100 mg/L. 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.</description><identifier>ISSN: 1042-6507</identifier><identifier>EISSN: 1563-5325</identifier><identifier>DOI: 10.1080/10426500903251373</identifier><language>eng</language><publisher>Abingdon: Taylor &amp; Francis Ltd</publisher><subject>Derivatives</subject><ispartof>Phosphorus, sulfur, and silicon and the related elements, 2010-08, Vol.185 (8), p.1746</ispartof><rights>Copyright Taylor &amp; Francis Ltd. 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title Synthesis and Herbicidal Activity of [alpha]-Amino Phosphonate Derivatives Containing Thiazole and Pyrazole Moieties
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