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Eugenol ester analogue and its preparation method and insecticide

A technology for eugenol esters and analogs, applied to eugenol ester analogs and their application fields, can solve the problems of poor ester solubility, limited application scope, low hydrophobicity, etc. Effect, simple preparation method

Active Publication Date: 2021-01-15
HUNAN AGRI BIOTECH RES CENT
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] As a phenol analogue, eugenol has low hydrophobicity, weak ester solubility, and weak penetration ability to the epidermis of pest cells, so its activity as a pesticide is not very high
thus limiting its scope of application

Method used

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  • Eugenol ester analogue and its preparation method and insecticide
  • Eugenol ester analogue and its preparation method and insecticide
  • Eugenol ester analogue and its preparation method and insecticide

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preparation example Construction

[0027] The present invention also provides a kind of preparation method of described eugenol ester analogue, comprises the following steps:

[0028] (1) peracyl chlorination of the substituted carboxylic acid to obtain an intermediate product;

[0029] (2) reacting the intermediate product and eugenol in the presence of an acid-binding agent and an organic solvent to obtain the eugenol ester analogue;

[0030] Wherein, the substituent in the substituted carboxylic acid is selected from one of C1-C10 alkyl, C1-C10 alkenyl, aryl, furyl and imidazolyl.

[0031] According to the present invention, the synthetic route of described eugenol ester analog is as follows:

[0032]

[0033] According to the present invention, under preferred conditions, the peracylchlorination process of the substituted carboxylic acid is as follows: uniformly mix the substituted carboxylic acid and thionyl chloride in an organic solvent, heat and reflux at 60°C for 5h, and then cool to 25°C , under ...

Embodiment 1

[0044] Preparation of phenyl 4-propenyl-2-methoxybenzoate

[0045] Mix 10ml of thionyl chloride with 1.00g of benzoic acid (8.19mmol) in dichloromethane evenly, then heat to reflux at 60°C for 5h, then cool to 25°C, at a temperature of 45°C and a pressure of 760mmHg Excess thionyl chloride and dichloromethane were distilled off under reduced pressure to obtain intermediate product 1 as white powder.

[0046] The intermediate product 1 (8.19mmol), 10ml of dichloromethane, 1.34g (8.19mmol) of eugenol, 1ml of triethylamine were stirred at 25°C for 3h, concentrated under reduced pressure, and column chromatography (V 洗脱液 :V 乙酸乙酯 :V 石油醚 =1:3:2) 1.97g of white solid (I1) was obtained with a yield of 90%. The results are shown in Table 1.

[0047] 1 H NMRδ: 2.91(s,3H,CH 3 ), 3.38~3.40 (d, 2H, J=6.00Hz, CH 2 ),3.83(s,1H,OCH 3),5.08~5.31(m,1H,ArH),6.76~6.80(m,2H,ArH),6.94~6.97(m,1H,ArH).

Embodiment 2

[0049] Preparation of methyl 4-propenyl-2-methoxyphenylfuran-2-carboxylate (I2)

[0050] Mix 10ml of thionyl chloride with 1.00g of furancarboxylic acid (8.92mmol) in dichloromethane evenly, then heat to reflux at 60°C for 1h, then cool to 25°C, at a temperature of 45°C and a pressure of 760mmHg The excess thionyl chloride and dichloromethane were distilled off under reduced pressure to obtain white powder intermediate product 2, and the results are shown in Table 1.

[0051] The intermediate product 2 was stirred with 10ml of dichloromethane, 1.52g (8.92mmol) of eugenol, and 1ml of triethylamine in a three-necked flask at 25°C for 4h, then concentrated under reduced pressure, and column chromatography (V 洗脱液 :V 乙酸乙酯 :V 石油醚 =1:1:2) to obtain 1.97g white powder (I2), yield 66%.

[0052] 1 H NMRδ: 3.40~3.42 (d, 2H, J=6.00Hz, CH 2 ),3.82(s,1H,OCH 3 ), 5.09~5.16(m,2H,CH), 5.98~6.00(m,2H,CH), 6.80~6.84(m,2H,CH), 7.06~7.08(m,2H,CH), 7.39~7.40( m, 1H, ArH), 7.67-7.68 (m, 1H, A...

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Abstract

The invention relates to a eugenol ester analogue and application thereof and in particular relates to the eugenol ester analogue and a preparation method thereof as well as insecticide. The preparation method of the eugenol ester analogue comprises the following steps: (1) carrying out acylating chlorination on substituted carboxylic acid to obtain an intermediate product; (2) enabling the intermediate product and eugenol to react under the condition that an acid binding agent and an organic solvent exist, so as to obtain the eugenol ester analogue, wherein a substituent group in the substituted carboxylic acid is selected from one of C1 to C10 alkyl, C1 to C10 alkenyl, aryl, furyl and imidazolyl. The eugenol ester analogue prepared by the method provided by the invention has a remarkablelethal effect on agricultural insect pests and the insect pests also can have an octopamine agonist poisoning symptom; the eugenol ester analogue can be used as the insecticide and is widely appliedto agriculture.

Description

technical field [0001] The invention relates to a eugenol ester analog and its application, in particular to a eugenol ester analog, a preparation method thereof and an insecticide. Background technique [0002] Using natural active substances as lead compounds includes discovering pesticide active compounds directly from natural products and modifying the chemical structure or molecular modification of natural compounds, so as to develop new pesticide varieties, which is one of the effective ways to research new pesticides. According to reports, there are at least 2,000 species of plants in the world that have insecticidal, acaricidal or bactericidal activities. So far, a variety of commercial pesticides have been developed using natural products as lead compounds. [0003] As a plant essential oil, eugenol exists widely in various plants. Because of its various biological activities, it has important research value in the field of drug development. In terms of medicine, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/78C07C69/16C07C69/08C07C69/587C07D307/68C07D261/18A01N37/10A01N37/02A01N37/06A01N43/08A01N43/56A01P7/04
CPCA01N37/02A01N37/06A01N37/10A01N43/08A01N43/56C07C69/08C07C69/16C07C69/587C07C69/78C07D261/18C07D307/68
Inventor 邓希乐周小毛郑文娜
Owner HUNAN AGRI BIOTECH RES CENT
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