Application of paclobutrazol and its analogs in wheat lodging resistance
A technology of paclobutrazol and the like is applied in the field of crop cultivation and can solve the problems of unfavorable crop rotation, long residual time, potential safety hazards and the like
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Embodiment 1
[0029] Example 1: N-(1-(4-(furan-2-yl)phenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl) Synthesis of -pentan-3-yl)benzamide
[0030] 1. 1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)-pentane-3-primary amine hydrochloride Synthesis of (Intermediate 1)
[0031]
[0032] 1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)-pentane-3-ol (100mmol) was added to 200ml In toluene, stir until completely dissolved, cool down to 0-5°C, add triphenylphosphine (120mmol) and succinimide (120mmol) to the system, drop diethyl azodicarboxylate (100mmol) in toluene After the solution was added dropwise, keep the temperature and stir for 1h, then return to room temperature and continue to stir for 6h. Remove toluene under reduced pressure, add 250g water to the residue, heat up to reflux, then cool down to 60-65°C, add 10g concentrated hydrochloric acid, then heat up to reflux, stir for 1h, cool down to 80-90°C, add 400ml toluene, and heat up to Reflux, keep reflux for 1h, th...
Embodiment 2
[0044] Example 2: N-(1-(4-(furan-2-yl)phenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl) Synthesis of -pentan-3-yl)-2-methoxybenzamide
[0045]
[0046] 1-(4-(furan-2-yl)phenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)-pentane-3- The primary amine (intermediate 3) (100mmol) was dissolved in 150ml of dichloromethane, cooled to -5°C, and kept at the temperature, 2-methoxybenzoyl chloride (102mmol) was added dropwise to the reaction, and then N,N -Diisopropylethylamine (105mmol), warming up to room temperature, stirred for 10h, after the reaction was completed, concentrated under reduced pressure to remove the organic solvent, the residual solid was beaten with ethanol for 50 minutes, and suction filtered to obtain off-white solid N-(1- (4-(furan-2-yl)phenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)-pentane-3-yl)- 2-methoxybenzamide, 42.0 g, yield: 91.5%. LC-MS (ESI, pos, ion) m / z: 459[M+H].
Embodiment 3
[0047] Example 3: N-(1-(4-(furan-2-yl)phenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl) Synthesis of -pentan-3-yl) p-methoxybenzamide
[0048]
[0049] 1-(4-(furan-2-yl)phenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)-pentane-3- The primary amine (intermediate 3) (100mmol) was dissolved in 150ml of dichloromethane, cooled to -5°C, and kept at the temperature, p-methoxybenzoyl chloride (102mmol) was added dropwise to the reaction, and then N,N- Diisopropylethylamine (105mmol), warming up to room temperature, stirred and reacted for 10h, after the reaction was completed, concentrated under reduced pressure to remove the organic solvent, the residual solid was beaten with ethanol for 50 minutes, and suction filtered to obtain off-white solid N-(1-( 4-(furan-2-yl)phenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)-pentane-3-yl)p-methyl Oxybenzamide, 40.8g, yield: 89%. LC-MS (ESI, pos, ion) m / z: 459[M+H].
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