Application of 3,6-disubstituted imidazo[1, 2-b] pyridazine derivatives in preparation of fungicides
A technology of disubstituted imidazole and 2-b, applied in the field of pesticides, can solve problems such as unresearched inhibitory effects, and achieve the effect of strong bactericidal activity and broad-spectrum bactericidal activity
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[0030] Example 1
[0031] A preparation method of 6-chloro-3-phenylimidazo[1,2-b]pyridazine, comprising the following steps:
[0032] (1) Preparation of 6-chloroimidazo[1,2-b]pyridazine:
[0033] 3-Amino-6-chloropyridazine (3 g, 23 mmol) and n-butanol (30 mL) were added to a 100 mL round-bottomed flask, chloroacetaldehyde (4.6 mL, 50% aqueous solution) was added dropwise at room temperature, and the reaction was refluxed for 16 hours. After the reaction was completed, the reaction solution was cooled to room temperature, n-butanol was evaporated under reduced pressure, then 30 mL of water was added, and NaHCO 3 The solution was adjusted to pH 7, extracted with ethyl acetate (3 x 50 mL), anhydrous Na 2 SO 4 After drying, the organic phase was concentrated and purified by column chromatography to obtain 3.1 g of white solid compound 6-chloroimidazo[1,2-b]pyridazine (2), yield 90%, M.p.115-117°C; 1 H NMR (400MHz, CDCl 3 ): δ7.35(d,1H,J=9.6Hz),7.85(s,1H),8.22(d,1H,J=9.6Hz),8.34...
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[0039] Example 2
[0040] A method for preparing 6-chloro-3-(2,3-dichlorophenyl)imidazo[1,2-b]pyridazine, comprising the following steps:
[0041] The preparation steps (1) and (2) of Example 1 are the same, except that the phenylboronic acid in the step (3) of Example 1 is replaced by 2,3-dichlorophenylboronic acid to obtain compound 6 -Chloro-3-(2,3-dichlorophenyl)imidazo[1,2-b]pyridazine (4b), 48% yield, white solid, M.p.194-195°C, 1 H NMR (600MHz, CDCl 3 )δ7.99-7.98(m,2H),7.59(dd,1H,J=8.4Hz,1.8Hz),7.54(dd,1H,J=8.4Hz,1.2Hz),7.36(t,1H,J= 7.8Hz), 7.13(d, 1H, J=8.4Hz); 13 C NMR (150MHz, CDCl 3 )δ138.0,135.5,134.0,132.9,131.1,130.1,128.8,127.3,127.2,126.4,119.1.HRMS(ESI)calcd for C 12 H 7 N 3 Cl 3 [M+H] + m / z: 297.9706, found 297.9712.
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[0042] Example 3
[0043] A method for preparing 6-chloro-3-(2-fluorophenyl)imidazo[1,2-b]pyridazine, comprising the following steps:
[0044] The preparation steps (1) and (2) of Example 1 are the same, except that the phenylboronic acid in the step (3) of Example 1 is replaced by 2-fluorophenylboronic acid to obtain the compound 6-chloro- 3-(2-Fluorophenyl)imidazo[1,2-b]pyridazine (4c), 77% yield, white solid, M.p.70-72°C, 1 H NMR (400MHz, CDCl 3 )δ8.21(td,1H,J=7.6Hz,2.4Hz),8.15(d,1H,J=2.8Hz),8.00(d,1H,J=9.2Hz),7.41-7.38(m,1H) ,7.33-7.30(m,1H),7.24-7.22(m,1H),7.13(d,1H,J=9.6Hz); 13 C NMR (100MHz, CDCl 3 )δ159.8,157.3,145.7,134.8,134.7,128.9,128.1,126.1,123.1,117.5,115.0,114.8.HRMS(ESI)calcd for C 12 H 8 N 3 FCl[M+H] + m / z: 248.0391, found 248.0400.
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