Oxdiazole compound containing pyrazole ring, preparation method and applications thereof
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A technology of oxadiazoles and compounds, applied in the field of oxadiazoles
Active Publication Date: 2013-01-02
菏泽建数智能科技有限公司
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[0003] However, no information on 2-substituted benzylthio-5-((3,5-dimethyl-1 H -Pyrazol-1-yl)methyl)-1,3,4-oxadiazole Derivatives Synthesis and Biological Activity Research Reports
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Embodiment 1
[0023] 2-Benzylthio-5-((3,5-dimethyl-1 H -Pyrazol-1-yl)methyl)-1,3,4-oxadiazole ( Ia ): White crystals, yield 67.1%, melting point 64-65°C; 1 H NMR (CDCl 3 , 400 MHz), δ: 7.29-7.38(m, 5H, ArH), 5.86(s, 1H, PyH), 5.35(s, 2H, Py-CH 2 ), 4.43(s, 2H, S-CH 2 ), 2.28(s, 3H, Py-CH 3 ), 2.21(s, 3H, Py-CH 3 ). MS (ESI), m / z: 299 (M -1). Elemental anal. (%), calculated: C, 59.98; H, 5.37; N, 18.65; found: C, 60.21; H, 5.61; N , 18.51.
Embodiment 2
[0025] 2-(2,4-Dichlorobenzylthio)-5-((3,5-dimethyl-1 H -Pyrazol-1-yl)methyl)-1,3,4-oxadiazole (Ib): White crystals, the yield is 77.1%, the melting point is 83-84°C; 1 H NMR (CDCl 3 , 400 MHz), δ: 7.48(d, J=7.95Hz, 1H, ArH), 7.40(s, 1H, Ar-H), 7.16(d, J=8.22Hz, 1H, ArH), 5.86(s, 1H, PyH), 5.34(s, 2H, Py-CH 2 ), 4.48(s, 2H, S-CH 2 ), 2.28(s, 3H, Py-CH 3 ), 2.21(s, 3H, Py-CH 3 ). MS (ESI), m / z: 368 (M -1). Elemental anal. (%), calculated: C, 48.79; H, 3.82; N, 15.17; found: C, 48.98; H, 4.12; N ,15.09.
Embodiment 3
[0027] 2-(3-Chlorobenzylthio)-5-((3,5-dimethyl-1 H -Pyrazol-1-yl)methyl)-1,3,4-oxadiazole (Ic): White crystal, yield 83.4%, melting point 67-68℃; 1 H NMR (CDCl 3 , 400 MHz), δ: 7.39(s, 1H, ArH), 7.27-7.32(m, 2H, Ar-H), 7.10-7.23(m, 2H, ArH), 5.86(s, 1H, PyH), 5.34 (s, 2H, Py-CH 2 ), 4.38(s, 2H, S-CH 2 ), 2.28(s, 3H, Py-CH 3 ), 2.21(s, 3H, Py-CH 3 ). MS (ESI), m / z: 333 (M -1). Elemental anal. (%), calculated: C, 53.81; H, 4.52; N, 16.73; found: C, 53.42; H, 4.89; N , 16.38.
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Abstract
The present invention relates to an oxdiazole compound containing a pyrazole ring, and a preparation method thereof. The oxdiazole compound of the present invention has a structure represented by a formula (I), wherein R is a substituted phenyl, the benzene ring on the substituted phenyl is monosubstituted or polysubstituted, the substituted group is independently selected from one of H, C1-C6 alkyl, halogen, cyano, and nitro. The oxdiazole compound of the present invention has characteristics of simple preparation and excellent bactericidal activity, and can be used as a bactericidal agent for prevention and control of cucumber tan disease, cucumber bacterial angular leaf spotdisease, cucumber gummy stem blight, cucumber downy mildew, and cucumber sclerotiumdisease. The present invention further relates to a bactericidal agent containing the compound.
Description
(1) Technical field [0001] The invention relates to an oxadiazole compound containing a pyrazole ring, namely 2-substituted benzylthio-5-((3,5-dimethyl-1 H -Pyrazol-1-yl)methyl)-1,3,4-oxadiazole derivatives and their preparation and application. (2) Background technology [0002] Heterocyclic compounds have become the mainstream in the development of new pesticides, and in heterocyclic compounds, nitrogen-containing heterocycles are the main ones. 1,3,4-Oxadiazole compounds also have very important biological activities, including anti-inflammatory, anti-cancer, anti-viral, antibacterial and herbicidal activities. For example, the synthetic 2-substituted pyrazole-5-methylthio-1,3,4-oxadiazole exhibited good inhibitory activity against rice sheath blight at 100 mg / L; 2-methyl-5 -Substituted benzylthio-1,3,4-oxadiazoles have good inhibitory effect on rapeseed at 100ppm. As an important branch of heterocyclic compounds, the pyrazole ring is the core structural unit of many n...
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