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Diester-substituted methyl salicylate analogue and preparation method and application thereof

The technology of a drug and an alkyl group is applied to the methyl salicylate analog substituted by the diester group and its preparation, and the application fields in the control of aphids and the attraction of natural enemies can solve the problems of short shelf life, limited sources of volatiles and irregular structure. stability and other issues, to achieve the effects of low cost, simple and easy preparation method, and diverse functions

Active Publication Date: 2022-01-04
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the limited sources of natural plant volatiles, the structure is unstable, and the shelf life is short, it has limitations in practical applications.

Method used

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  • Diester-substituted methyl salicylate analogue and preparation method and application thereof
  • Diester-substituted methyl salicylate analogue and preparation method and application thereof
  • Diester-substituted methyl salicylate analogue and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Example 1, Preparation of 1-(E)-3,7-dimethyl-2,6-octadiene-2-(acetoxy)-3-methoxybenzoate (A-01)

[0057] In a 100 mL three-necked flask, 2.18 g of 3-methoxysalicylic acid, 3.22 g of DCC (dicyclohexylcarbodiimide) and 1.74 g of DMAP (4-dimethylaminopyridine) were added. Dissolve in 40 mL of tetrahydrofuran, add 2.00 g of geraniol dropwise, and react at 20°C for 3 h. Extract with water three times, obtain organic phase, remove solvent under reduced pressure, silica gel column chromatography (eluent is sherwood oil: ethyl acetate=V 1 :V 2 =50:1), a yellow liquid was obtained, and the product was 1-(E)-3,7-dimethyl-2,6-octadiene-2-hydroxyl-3-methoxybenzoate, the yield 53.8%.

[0058] In a 50mL three-necked flask, add 2g 1-(E)-3,7-dimethyl-2,6-octadiene-2-hydroxyl-3-methoxybenzoate (6.6mmol), then Add 30ml of dichloromethane to dissolve and stir well. Add 1.34g triethylamine (13.2mmol) afterwards as acid-binding agent, ice-bath cooling. Dissolve 1.05g of acetyl chlorid...

Embodiment 2

[0059] Example 2, 1-(E)-3,7-dimethyl-2,6-octadiene-2-(propionyloxy)-3-methoxybenzoate (A-02) preparation

[0060] In a 100 mL three-necked flask, 2.18 g of 3-methoxysalicylic acid, 3.22 g of DCC (dicyclohexylcarbodiimide) and 1.74 g of DMAP (4-dimethylaminopyridine) were added. Dissolve in 40 mL of tetrahydrofuran, add 2.00 g of geraniol dropwise, and react at 20°C for 3 h. Extract with water three times, obtain organic phase, remove solvent under reduced pressure, silica gel column chromatography (eluent is sherwood oil: ethyl acetate=V 1 :V 2 =50:1), a yellow liquid was obtained, and the product was 1-(E)-3,7-dimethyl-2,6-octadiene-2-hydroxyl-3-methoxybenzoate, the yield 53.8%.

[0061] In a 50mL three-necked flask, add 2g 1-(E)-3,7-dimethyl-2,6-octadiene-2-hydroxyl-3-methoxybenzoate (6.6mmol), then Add 30ml of tetrahydrofuran to dissolve and stir evenly. Then add 0.782g pyridine (9.9mmol) as an acid-binding agent, and cool down in an ice bath. Dissolve 1.22g of propi...

Embodiment 3

[0062] Example 3, 1-(E)-3,7-dimethyl-2,6-octadiene-2-(butyryloxy)-3-methoxybenzoate (A-03) preparation

[0063] In a 100 mL three-necked flask, 2.18 g of 3-methoxysalicylic acid, 3.22 g of DCC (dicyclohexylcarbodiimide) and 1.74 g of DMAP (4-dimethylaminopyridine) were added. Dissolve in 40 mL of tetrahydrofuran, add 2.00 g of geraniol dropwise, and react at 20°C for 3 h. Extracted three times with water to obtain the organic phase, removed the solvent under reduced pressure, and separated by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = V1: V2 = 50:1) to obtain a yellow liquid, the product was 1-(E )-3,7-dimethyl-2,6-octadiene-2-hydroxy-3-methoxybenzoate, yield 53.8%.

[0064] In a 50mL three-necked flask, add 2g 1-(E)-3,7-dimethyl-2,6-octadiene-2-hydroxyl-3-methoxybenzoate (6.6mmol), then Add 30ml of ethyl acetate to dissolve and stir well. Then add 0.58g of butyric acid (6.6mmol) and 30ml of ethyl acetate solution to dissolve evenly, stir, a...

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Abstract

The invention provides a diester-substituted methyl salicylate analogue and a preparation method and application thereof. The structural formula is shown as a formula A. The diester-substituted methyl salicylate analogue has the advantages of simple and feasible preparation method, simplicity in operation, easiness in product purification, lower cost and multiple biological activities. The diester-substituted methyl salicylate analogue not only has an effect on aphids, but also has the potential of attracting natural enemies of the aphids. The diester-substituted methyl salicylate analogue can be used as a behavior control agent for aphids and natural enemies thereof, and is applied to green prevention and control of agricultural pests.

Description

technical field [0001] The invention belongs to the field of agricultural chemicals, and in particular relates to a diester-substituted methyl salicylate analogue and a preparation method thereof, as well as the application of the compound in aphid control and (aphid) natural enemy attraction. Background technique [0002] Aphids are one of the main pests in agriculture, causing very serious damage to plants. Aphids mainly cause harm to plants by sucking plant juices. What's more, aphids can also spread various plant viruses, causing huge economic losses to agricultural production. Therefore, effective control of aphids can achieve the purpose of pest control and disease prevention, which is of great significance in agricultural production. The control of aphids currently mainly adopts the method of chemical pesticide control. Due to the resistance of aphids to traditional chemical aphidicides, the amount of pesticides used continues to increase. The toxicity of some chemic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/92C07C69/86C07D333/38A01N37/40A01N43/10A01N53/10A01P7/04A01P19/00
CPCC07C69/92C07C69/86C07D333/38A01N37/40A01N43/00C07C2601/02C07C2601/04C07C2601/08C07C2601/14
Inventor 杨新玲杨朝凯潘世香刘彦秦耀果凌云石卓
Owner CHINA AGRI UNIV