Synthesis method of chalcone-containing aryloxy-carboxylate compounds and application of chalcone-containing aryloxy-carboxylate compounds in pesticide
A technology of ester compounds and aryloxycarboxylic acids, applied in the field of herbicides, can solve problems such as poor application potential, and achieve the effects of high control efficiency, improved herbicidal activity and high herbicidal activity
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Embodiment 1
[0033] Example 1: Preparation of 4-(2,4-dichlorophenoxyacetoxy)-chalcone (I1):
[0034]
[0035] 4-Hydroxychalcone (0.23g, 1.0mmol) was added to a container containing 2,4-dichlorophenoxyacetyl chloride (0.25g, 1.0mmol) and CH 2 Cl 2 (5mL), then dry triethylamine (200μL) was added in batches, stirred at room temperature for 8h, TLC detected that the reaction was complete, the solvent was removed under reduced pressure, 100mL of 1% NaOH solution was added thereto to remove unreacted raw materials, Filter, wash with distilled water and a small amount of ethanol until pH = 7, dry, and recrystallize the filter cake with methanol and water to obtain 0.33 g of 4-(2,4-dichlorophenoxyacetoxy)-chalcone (I1). Rate 77.0%, mp: 159~160℃; 1 H NMR (400MHz, CDCl 3 )δ: 8.09~8.05(m, 2H), 7.82(d, J=15.2Hz, 1H), 7.65~7.63(m, 2H), 7.49(d, J=15.8Hz, 1H), 7.44~7.41(m ,4H),7.30~7.27(m,2H),7.21(dd,J=8.8,2.5Hz,1H),6.92(d,J=8.8Hz,1H),4.96(s,2H). 13 C NMR (100MHz, CDCl 3 )δ: 189.1, 166.2, 153.3,...
Embodiment 2
[0036] Example 2: Preparation of 4-(2,4-dichlorophenoxyacetoxy)-4'-methylchalcone (I2):
[0037]
[0038] 4-Hydroxy-4'-methylchalcone (0.24g, 1.0mmol) was added to 2,4-dichlorophenoxyacetyl chloride (0.38g, 1.5mmol) and CHCl 3 (5mL) solution, then dry pyridine (200μL) was added in batches, stirred at 0°C for 24h, TLC detected that the reaction was complete, the solvent was removed under reduced pressure, 100mL of 1% NaOH solution was added thereto to remove unreacted raw materials, filtered , washed with distilled water and a small amount of ethanol to pH=7, dried, and the filter cake was recrystallized from ethyl acetate and dichloromethane to obtain 4-(2,4-dichlorophenoxyacetoxy)-4′-methylchar Ketone (I2) 0.37g, yield 85.2%, mp: 177~178°C; 1 H NMR (400MHz, CDCl 3 )δ: 8.06(d, J=8.4Hz, 2H), 7.79(d, J=15.7Hz, 1H), 7.53(d, J=7.5Hz, 2H), 7.47~7.42(m, 2H), 7.27~ 7.25(m,2H),7.23~7.20(m,3H),6.92(d,J=8.8Hz,1H),4.96(s,2H),2.39(s,3H). 13 C NMR (100MHz, CDCl 3 )δ: 189.2, 166.2, ...
Embodiment 3
[0039] Example 3: Preparation of 4-(2,4-dichlorophenoxyacetoxy)-3',4'-dimethylchalcone (I3):
[0040]
[0041] 4-Hydroxy-3',4'-dimethylchalcone (0.25g, 1.0mmol) was added to a container containing 2,4-dichlorophenoxyacetyl chloride (0.38g, 1.5mmol) and 1,2- Dichloroethane (5mL) solution, then dry triethylamine (200μL) was added in batches, refluxed and stirred for 1.0h, TLC detected that the reaction was complete, the solvent was removed under reduced pressure, and 100mL of 1% NaOH solution was added thereto to remove Unreacted raw materials were filtered, washed with distilled water and a small amount of ethanol to pH=7, dried, and the filter cake was recrystallized with ethyl acetate and dichloromethane to obtain 4-(2,4-dichlorophenoxyacetoxy)-3 ',4'-Dimethylchalcone (I3) 0.38g, yield 83.0%, mp: 174~175℃; 1 H NMR (400MHz, CDCl 3)δ: 8.08~8.06(m,2H),7.78(d,J=15.4Hz,1H),7.47~7.42(m,2H),7.42~7.37(m,2H),7.28~7.25(m,2H) ,7.21(dd,J=8.7,2.5Hz,1H),7.18(d,J=7.8Hz,1H),6.92(d,J=9....
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