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Heterocycle-containing dehydroabietylformamide compound as well as preparation method and application thereof

A technology for abietylformamide and dehydroabietylamine, which is applied in the field of dehydroabietylformamide compounds and their preparation, can solve problems such as no dehydroabietylformamide compounds, and achieves novel molecular structure and reaction conditions. Easy-to-control, easy-to-prepare effect

Pending Publication Date: 2021-12-10
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, there is no report on the use of heterocycle-containing dehydroabietyl formamide compounds as agricultural fungicides

Method used

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  • Heterocycle-containing dehydroabietylformamide compound as well as preparation method and application thereof
  • Heterocycle-containing dehydroabietylformamide compound as well as preparation method and application thereof
  • Heterocycle-containing dehydroabietylformamide compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] The preparation of the dehydroabietyl carboxamide compound containing heterocycle:

[0016] Take 2-methylfuran-3-carboxylic acid (1.20mmol) and dehydroabietylamine (1.0mmol) in a one-necked bottle, add dichloromethane (10mL) to dissolve, add catalyst 4-dimethylaminopyridine (0.20mL) under stirring mmol) and condensing agent EDCI (1.20mmol), after addition, react at 25°C for 6-10h, TLC detection, after the reaction is complete, wash the organic layer with saturated sodium bicarbonate solution, wash with water, wash with saturated saline, and dry over anhydrous sodium sulfate , filtered with suction, concentrated under reduced pressure to remove dichloromethane to obtain a crude product, purified by silica gel column chromatography (eluent dichloromethane) and dried to obtain the target compound.

[0017]

[0018] Compound I-1. Yield, 75%, white wax. 1 H NMR (600MHz, CDCl 3 )δ7.22(d, J=2.0Hz, 1H), 7.16(d, J=8.2Hz, 1H), 6.99(dd, J 1 =8.1Hz,J 2 =1.5Hz,1H),6.89(s,1H),...

Embodiment 2

[0020]

[0021] Take 2-fluoropyridine-3-carboxylic acid (1.20mmol) and dehydroabietylamine (1.0mmol) in a one-necked bottle, add dichloromethane (10mL) to dissolve, add the catalyst 4-dimethylaminopyridine (0.20mmol) under stirring and condensing agent EDCI (1.20mmol), after adding, react at 25°C for 6-10h, TLC detection, the reaction is completed, the organic layer is washed with saturated sodium bicarbonate solution, washed with water, washed with saturated saline, dried over anhydrous sodium sulfate, pumped Filtrate, concentrate under reduced pressure to remove dichloromethane to obtain a crude product, purify by silica gel column chromatography (eluent dichloromethane) and dry to obtain the target compound I-2, yield, 75%, white solid; m.p.79-80.5°C.m.p. 79-80.5°C; 1 H NMR (400MHz, CDCl 3 )δ8.49–8.45(m,1H),8.21(d,J=4.5Hz,1H),7.26-7.23(m,1H),7.08(d,J=8.2Hz,1H),6.90(d,J =8.1Hz,1H),6.85–6.79(m,2H),3.39(dd,J 1 =13.6Hz,J 2 =6.1Hz, 1H), 3.29(dd, J1=13.6Hz, J2=6.3Hz, 1H), ...

Embodiment 3

[0023]

[0024] Take 2-chloropyridine-3-carboxylic acid (1.20mmol) and dehydroabietylamine (1.0mmol) in a single-necked bottle, add dichloromethane (10mL) to dissolve, add the catalyst 4-dimethylaminopyridine (0.20mmol) under stirring and condensing agent EDCI (1.20mmol), after adding, react at 25°C for 6-10h, TLC detection, the reaction is completed, the organic layer is washed with saturated sodium bicarbonate solution, washed with water, washed with saturated saline, dried over anhydrous sodium sulfate, pumped Filter, concentrate under reduced pressure to remove dichloromethane to obtain a crude product, purify by silica gel column chromatography (eluent dichloromethane) and dry to obtain the target compound I-3. Yield 80%, white solid; m.p.86-87°C. 1 H NMR (400MHz, CDCl 3 )δ8.29(d, J=4.3Hz, 1H), 7.93(d, J=7.4Hz, 1H), 7.18–7.16(m, 1H), 7.06(d, J=8.1Hz, 1H), 6.89( d,J=8.1Hz,1H),6.79(s,1H),6.58(t,J=5.4Hz,1H),3.30(d,J=9.4Hz,2H),2.87–2.68(m,3H), 2.21(d, J=12.8Hz, 1H), 1.88...

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Abstract

The invention discloses a heterocycle-containing dehydroabietylformamide compound and a preparation method and application thereof. The name of the compound is heterocycle-containing dehydroabietylformamide; the structural formula of the compound is as shown in the specification. The heterocycle-containing dehydroabietylformamide compound is applied to prevention and treatment of plant fungi in agriculture or forestry. An activity result shows that the compound disclosed by the invention has a relatively good prevention and treatment effect on sclerotinia sclerotiorum and botrytis cinerea and shows certain bacteriostatic activity on alternaria solani, fusarium graminearum and rice sheath blight disease.

Description

technical field [0001] The invention belongs to the field of pesticide synthesis, and in particular relates to a class of heterocycle-containing dehydroabietyl carboxamide compounds and a preparation method and application thereof. Background technique [0002] Pine resin is the main component in natural pine trees. Pine resin contains two components: abietic acid and turpentine. Rosin acid has the functions of drying dampness and killing insects, pulling out toxins and promoting granulation, relieving itching and relieving pain, and is a commonly used medicine in surgery. Clinically, it is often researched together with other medicines and made into fine powder and applied to the affected area to treat symptoms such as boils, carbuncles, eczema, impetigo, and skin bleeding from knife wounds. [0003] Abietic acid is dehydroabietic acid, and dehydroabietylamine is a derivative of dehydroabietic acid. It is an important raw material for replacing carboxylic acid groups with ...

Claims

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Application Information

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IPC IPC(8): C07D307/68
CPCC07D307/68C07D213/82C07D231/14C07C231/02C07C233/65C07D261/18C07D277/56C07D237/24C07D311/12C07D317/46C07D333/70C07D239/28C07D209/42C07D231/56C07D241/44C07D277/68C07D271/06C07D231/12A01N43/08A01N43/10A01N43/12A01N43/16A01N43/32A01N43/50A01N43/56A01N43/54A01N43/58A01N43/60A01N43/78A01N43/80A01N43/82A01N37/18C07C2603/26
Inventor 谷文杨子辉刘青松孙月王石发孙雪宝孙露陈霖霖
Owner NANJING FORESTRY UNIV
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