Synthesis and Fungicidal Activity of O,O'-Dimethyl α-[(5-Ethoxycarbonyl-4- Methyl-1,3-Thiazol-2-YL-Amino)Arylmethane] Phosphonates

Abstract

A series of dialkyl [(5-ethoxycarbonyl-4-methyl-1,3-thiazol-2-ylamino)arylmethane] phosphonates was synthesized by the reaction of ethyl 2-amino-4-methylthiazole-5-carboxylate, with dialkyl phosphite and aromatic aldehydes using Mg(ClO₄)₂ as the catalyst. All new compounds were identified by elemental analysis, IR, ¹H NMR, and ¹³C NMR spectra. O,O'-Dimethyl α-[(5-Ethoxycarbonyl-4-methyl-1,3-thiazol-2-ylamino)arylmethane] phosphonate was further analyzed by a single-crystal X-ray diffraction analysis. The result of a preliminary bioassay indicated that some compounds exhibit inhibition activities against Rhizoctonia solani and Botrytis cinereapers at a dosage of 100 mg/L.

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Keywords:

• Amino phosphonate
• fungicidal activity
• synthesis
• thiazole

Acknowledgments

The present work was supported by the National Basic Research Program of China (No. 2003CB114400) and the National Natural Science Foundation of China (No.20372023, 20772042).

Notes

^a Condition 1: catalyzed by Mg(ClO₄)₂ in THF.

^b Condition 2: catalyzed by Mg(ClO₄)₂ under solvent-free condition.