Citation:
CHEN Min, YANG Chun-Long. Synthesis, Crystal Structure and Biological Activity of 5-(2-Methylphenyl)-1,3,4-oxadiazol-2(3H)-one Derivatives[J]. Chinese Journal of Structural Chemistry,
2015, 34(2): 189-196.
doi:
10.14102/j.cnki.0254-5861.2011-0467
Synthesis, Crystal Structure and Biological Activity of 5-(2-Methylphenyl)-1,3,4-oxadiazol-2(3H)-one Derivatives
摘要:
3-Methyl-5-(2-methylphenyl)-1,3,4-oxadiazol-2(3H)-one (6) and N,N-diethyl-2-(2-methylbenzoyl)-hydrazinecarboxamide (7) were designed and synthesized from 5-(2-methylphenyl)-1,3,4-oxadiazol-2(3H)-one (5) by substituting and ring-opening, respectively. The target compounds were confirmed by IR, 1H NMR spectroscopy, MS, elemental analysis and single-crystal X-ray diffraction. Compound 6 (C10H10N2O2, Mr=190.20) crystallizes in the triclinic system, space group P1 with a=7.4645(16), b=10.868(2), c=12.970(3)Å, α=110.542(2), β=98.142(2), γ=99.766(2)°, V=947.7(3)Å3, Z=4, F(000)=400, Dc=1.333 g/cm3, μ=0.095 mm-1, the final R=0.0550 and wR=0.1483 for 2956 observed reflections with I>2σ(I). Compound 7 (C13H19N3O2, Mr=249.31) crystallizes in the monoclinic system, space group C2/c with a=18.926(3), b=12.1853(17), c=14.740(2)Å, β=125.6380(10)°, V=2762.7(7)Å3, Z=8, F(000)=1072, Dc=1.199 g/cm3, μ=0.083 mm-1, the final R=0.0554 and wR=0.1468 for 2395 observed reflections with I>2σ(I). The preliminary bioassay results indicate that compound 6 exhibits notable fungicidal activities against Fusarium graminearum, Botrytis cinerea, Rhizoctonia cerealis and Colletotrichum capsici at the concentration of 100 μg/mL.
English
Synthesis, Crystal Structure and Biological Activity of 5-(2-Methylphenyl)-1,3,4-oxadiazol-2(3H)-one Derivatives
Abstract:
3-Methyl-5-(2-methylphenyl)-1,3,4-oxadiazol-2(3H)-one (6) and N,N-diethyl-2-(2-methylbenzoyl)-hydrazinecarboxamide (7) were designed and synthesized from 5-(2-methylphenyl)-1,3,4-oxadiazol-2(3H)-one (5) by substituting and ring-opening, respectively. The target compounds were confirmed by IR, 1H NMR spectroscopy, MS, elemental analysis and single-crystal X-ray diffraction. Compound 6 (C10H10N2O2, Mr=190.20) crystallizes in the triclinic system, space group P1 with a=7.4645(16), b=10.868(2), c=12.970(3)Å, α=110.542(2), β=98.142(2), γ=99.766(2)°, V=947.7(3)Å3, Z=4, F(000)=400, Dc=1.333 g/cm3, μ=0.095 mm-1, the final R=0.0550 and wR=0.1483 for 2956 observed reflections with I>2σ(I). Compound 7 (C13H19N3O2, Mr=249.31) crystallizes in the monoclinic system, space group C2/c with a=18.926(3), b=12.1853(17), c=14.740(2)Å, β=125.6380(10)°, V=2762.7(7)Å3, Z=8, F(000)=1072, Dc=1.199 g/cm3, μ=0.083 mm-1, the final R=0.0554 and wR=0.1468 for 2395 observed reflections with I>2σ(I). The preliminary bioassay results indicate that compound 6 exhibits notable fungicidal activities against Fusarium graminearum, Botrytis cinerea, Rhizoctonia cerealis and Colletotrichum capsici at the concentration of 100 μg/mL.
-
Key words:
- oxadiazole
- / hydrazinecarboxamide
- / synthesis
- / crystal structure
- / fungicidal activity
-
-
扫一扫看文章
计量
- PDF下载量: 0
- 文章访问数: 1875
- HTML全文浏览量: 45
下载:
