Application of a class of 1,2,3-triazole-5-amide compounds as agricultural fungicides
A technology of amide compounds and agricultural fungicides, applied in class 1, can solve problems such as poor safety, weak work foundation, and late start
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Embodiment 1
[0017] Example 1: Preparation of 2-chloro-N-(1-(4-chlorophenyl)-1,2,3-triazole-5)benzamide (compound 1)
[0018]
[0019] Dissolve 2-chlorobenzoic acid in SOCl 2 Reflux at 80°C for 120 minutes, and distill under reduced pressure to remove excess SOCl 2 , Get o-chlorobenzoyl chloride. Under the condition of -78℃ and nitrogen protection, 2mmol of n-butyl lithium was added dropwise to 2mL of dry tetrahydrofuran, and then 2mmol of dry acetonitrile was slowly added dropwise. After stirring for 5 minutes, the substituted 4-chloro dissolved in 2mL of tetrahydrofuran Phenyl azide (2mmol) was slowly added dropwise into the reaction flask, returned to normal temperature and stirred for 120 minutes. After the reaction, purified by silica gel column to obtain 4-chlorophenyl-5-amino-1,2,3-triazole . Take 1 mL of o-chlorobenzoyl chloride, add 1 mmol 4-chlorophenyl-5-amino-1,2,3-triazole, add a small amount of NaH under ice bath, stir at room temperature overnight, and purify by silica gel col...
Embodiment 2
[0020] Example 2: Preparation of 2-chloro-N-(1-(4-fluorophenyl)-1,2,3-triazole-5)benzamide (compound 2)
[0021]
[0022] The preparation method is the same as in Example 1. Replace 4-chlorophenyl azide with 4-fluorophenyl azide to prepare the target compound. The product is a white powder with a yield of 62.3%. m.p.141.3-141.5℃. 1 H NMR(600MHz, DMSO-d 6 )δ10.96(s, 1H), 8.04(s, 1H), 7.69-7.65(m, 2H), 7.56-7.51(m, 4H), 7.44(dd, J=7.6, 1.8Hz, 1H). ESI -MS m / z: 317.07(C 15 H 11 ClFN 4 O, [M+H] + ).
Embodiment 3
[0023] Example 3: Preparation of 2-chloro-N-(1-(3,4-dichlorophenyl)-1,2,3-triazole-5)benzamide (compound 3)
[0024]
[0025] The preparation method is the same as in Example 1. Replace 4-chlorophenyl azide with 3,4-dichlorophenyl azide to prepare the target compound. The product is a white powder with a yield of 60.1%. m.p.155.1-155.5℃. 1 H NMR(600MHz, DMSO-d 6 )δ11.07(s, 1H), 8.07(s, 1H), 8.02(d, J=2.4Hz, 1H), 7.91(d, J=8.6Hz, 1H), 7.67(dd, J=8.6, 2.4 Hz, 1H), 7.60-7.55 (m, 2H), 7.53 (td, J=7.7, 1.5 Hz, 1H), 7.48-7.44 (m, 1H). ESI-MS m / z: 367.04 (C 15 H 10 Cl 3 N 4 O, [M+H] + ).
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