Preparation method and application of pyrazole oxime compound containing 3-aryl-1,2,4-oxadiazole heterocyclic structure
A compound, oxadiazole technology, applied in the field of pesticides, to achieve the effect of excellent control effect
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Embodiment 1
[0037] The synthesis of compound Ia (R in general formula II 3 = 4-CF 3 , R in III 1 for -CH 3 , R 2 for 4-I)
[0038]
[0039] In a 100 mL flask, 4 mmol of compound III and 30 mL of N,N-dimethylformamide were added, and then 4.8 mmol of compound II and 8 mmol of cesium carbonate were added thereto. Slowly heated to 90°C for 12 hours. Heating was stopped, and after the reaction solution was cooled, it was suction-filtered to remove the solid, the mother liquor was concentrated to dryness, and column chromatography was separated and purified to obtain the target compound Ia with a yield of 53.6%; 1 HNMR (400MHz, CDCl 3): δ8.24(d, J=8.0Hz, 2H, Ar-H), 7.92(s, 1H, CH=N), 7.77(d, J=8.0Hz, 2H, Ar-H), 7.58(d ,J=8.0Hz,2H,Ar-H),6.66(d,J=8.0Hz,2H,Ar-H),5.25(s,2H,CH 2 ),3.60(s,3H,N-CH 3 ),2.33(s,3H,CH 3 ); 13 C NMR (100MHz, CDCl 3 ): δ177.9, 168.8, 157.9, 148.9, 148.8, 144.0, 140.3, 134.6, 134.3, 131.3, 129.3, 127.4, 127.3, 126.5, 123.8, 118.9, 100.9, 88.1, 67.6, 35.7, 15....
Embodiment 2
[0041] The synthesis of compound Ib (R in the general formula II 3 = 4-CF 3 , R in III 1 for -CH 3 , R 2 for 4-F)
[0042] In a 100 mL flask, 5 mmol of compound III and 25 mL of acetone were added, and then 4 mmol of compound II and 6 mmol of 4-N,N-lutidine (DMAP) were added thereto. Heat to reflux for 15 hours. Heating was stopped, and after the reaction solution was cooled, it was suction-filtered to remove the solid, the mother liquor was concentrated to dryness, and column chromatography was separated and purified to obtain the target compound Ib with a yield of 51.2%; 1 H NMR (400MHz, CDCl 3 ): δ8.22(d, J=8.0Hz, 2H, Ar-H), 7.91(s, 1H, CH=N), 7.77(d, J=12.0Hz, 2H, Ar-H), 6.94-6.99 (m,2H,Ar-H),6.82-6.85(m,2H,Ar-H),5.25(s,2H,CH 2 ),3.62(s,3H,N-CH 3 ),2.33(s,3H,CH 3 ); 13 C NMR (100MHz, CDCl 3 ): δ178.0, 168.8, 161.4, 159.0, 153.9, 149.6, 148.8, 144.1, 134.6, 134.3, 131.3, 129.3, 127.3, 118.0, 117.9, 117.8, 100.6, 67.6, 35.7, 15.9.
Embodiment 3
[0044] The synthesis of compound Ic (R in the general formula II 3 = 4-CF 3 , R in III 1 for -CH 3 , R 2 for 3-CF 3 )
[0045] In a 100 mL flask, 4 mmol of compound III and 20 mL of acetonitrile were added, and then 6 mmol of compound II and 10 mmol of sodium bicarbonate were added thereto. Heat to reflux for 13 hours. Heating was stopped, and after the reaction liquid was cooled, it was suction-filtered to remove the solid, the mother liquor was concentrated to dryness, separated and purified by column chromatography to obtain the target compound Ic with a yield of 50.1%; 1 H NMR (400MHz, CDCl 3 ): δ8.22(d, J=8.0Hz, 2H, Ar-H), 7.94(s, 1H, CH=N), 7.77(d, J=8.0Hz, 2H, Ar-H), 7.31-7.42 (m,2H,Ar-H),7.18(s,1H,Ar-H),7.02(d,J=8.0Hz,1H,Ar-H),5.20(s,2H,CH 2 ),3.64(s,3H,N-CH 3 ),2.36(s,3H,CH 3 ); 13 C NMR (100MHz, CDCl 3 ): δ177.8, 168.8, 157.9, 149.0, 148.4, 143.8, 134.6, 134.3, 134.1, 133.8, 132.0, 131.3, 129.3, 127.3, 126.2, 123.4, 121.9, 119.8, 114.1, 100.3.9, 87.7
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