Synthesis, Crystal Structure and Fungicidal Activity of (Z)-3,3-Dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one O-[(5-Aryl-1,3,4-oxadiazol-2-yl)methyl] oxime

doi:10.7503/cjcu20170024

Abstract

Abstract:

A series of (Z)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one O-[(5-aryl-1,3,4-oxadiazol-2-yl)methyl] oxime(4a-4u) was designed and synthesized via the reaction between iodobenzene diacetate(IBD) and the intermediates, (E)-N'-substituted benzylidene-2-({(Z)-[3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ylidene] amino}oxy)acetohydrazide(3), which were prepared from (Z)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one oxime via etherification, hydrazinolysis and condensation with various of substituted benzaldehyde. The structures of target compounds 4 were confirmed by muclear magnetian resonance(NMR), high resolution mass spectrum(HRMS) and elemental analysis. The crystal structure of compound 4c was determined by X-ray diffraction analysis. The results of fungicidal activity indicated that some of the title compounds exhibited moderate control rate against Rhizoctonia solani at 500 mg/L and moderate inhibition rate against Sclerotonia sclerotiorum at 25 mg/L.

Key words: 1,3,4-Oxadiazole, Iodobenzene diacetate, Single-crystal structure, Fungicidal activity

CLC Number:

O626

TrendMD:

TAN Ying, XIAO Mengwu, YE Jiao, HU Aixi, ZENG Ziqing, OU Xiaoming. Synthesis, Crystal Structure and Fungicidal Activity of (Z)-3,3-Dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one O-[(5-Aryl-1,3,4-oxadiazol-2-yl)methyl] oxime[J]. Chem. J. Chinese Universities, 2017, 38(8): 1375.

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