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KMID : 0903520010440030191
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Journal of the Korean Society of Agricultural Chemistry and Biotechnology
2001 Volume.44 No. 3 p.191 ~ p.196
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Synthesis of Trifluoromethylated Dihydro-1,4-oxathiin Carboxanilides and Their Fungicidal Activity
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조광연/Cho, Kwang Yun
김진철/한호규/남기달/Kim, Jin Cheol/Hahn, Hoh Gyu/Nam, Kee Dal
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Abstract
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α, β-Unsaturated carboxanilides 5 with trifluromethylated dihydro-1,4-oxathiins were synthesized for the development of new agrochemical fungicide. Chlorination of trifluoromethylated β-keto ester 6 followed by the reaction with 1,2-mercaptoethanol gave intermediate 1,4-oxathiane 11. Without purification of 11, substitution of hydroxy group by chlorine, followed by dehydrochlorination of 10 in the presence of triethylamine afforded trifluoromethylated dihydro-1,4-oxathiin ethyl ester 9. Acylation of the hydroxy group of the carboxylic acid 12 followed by treatment of various amines gave the corresponding trifluoromethylated dihydro-1,4-oxathiin carboxamides 5. Antifungal screening (in vivo) of the synthesized compounds against typical plant diseases, which include rice blast, rice sheath blight, cucumber gray mold, tomato late blight, wheat leaf rust, and barley powdery mildew, was carried out. Where meta position of the phenyl group was substituted with isopropoxy or isopropyl group, excellent antifungal activities against rice sheath blight and wheat leaf rust were detected.
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