2-芳基-5-(2′,3′,4′,6′-四-O-乙酰基-β-D-吡喃葡萄糖基)亚氨基-1,3,4-噻二唑啉的合成及其抑菌活性

SYNTHESIS AND FUNGICIDAL ACTIVITY OF 2-ARYL-5-(N-2′,3′,4′,6′-TETRA-O-ACETYL-β-D-GLUCOPYRANOSYL)IMIDO-1,3,4-THIADIAZOLINES

使 2 ,3 ,4,6 四 O 乙酰基 β D 吡喃葡萄糖基异硫氰酸酯依次与水合肼、芳醛反应 ,并在K3[Fe(CN) 6 ]和NaOH存在下于醇中环化制得 8种 2 芳基 5 (2′ ,3′ ,4′,6′ 四 O 乙酰基 β D 吡喃葡萄糖基 )亚氨基 1,3 ,4 噻二唑啉化合物 (Ⅳa～h)。所得化合物均经IR、1 HNMR进行了结构表征。初步抑菌活性测试结果表明 ,化合物Ⅳh 在质量浓度为 5 0× 10 - 6 g/L时对小麦赤霉菌的防效达 85 %。

Eight novel compounds of 2 aryl 5 ( N 2′,3′,4′,6′ tetra O acetyl β D glucopyranosyl) imido 1,3,4 thiadiazolinesⅣ a～h were synthesized from 2,3,4,6 tetra O acetyl β D glucopyranosyl isothiocyanate via 3 step reactions, i.e. (1) reaction with hydrazine, (2) reaction with aryl aldehyde and (3) cyclization in presence of K 3\[Fe(CN) 6\] and NaOH. These compounds were characterized by Elemental Analysis, IR and 1 H NMR. The preliminary fungicidal activity tests showed that the compound Ⅳ h provides 85% suppression against gibberella fujikuroi at 50×10 -6 g/L concentration.