Salicylic acid trans-(beta)-farnesene analogues and application thereof

A technology of farnesene and its analogues, which is applied in the field of salicylic acid trans-farnesene analogues and their preparation, which can solve the problems of limiting the application of EBF, unstable properties, and easy oxidation, and achieves a simple and convenient preparation method Ease of operation, low cost, and improved stability

Active Publication Date: 2015-06-10
CHINA AGRI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The structural formula of EBF is shown in Formula A: It is not difficult to find from the structural formula of EBF that it contains multiple double bonds, especially a pair of conjugated double bonds at the end, so EBF is easily oxidized and volatile in the air, and its properties are not good. Stable, limiting the application of EBF in the field

Method used

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  • Salicylic acid trans-(beta)-farnesene analogues and application thereof
  • Salicylic acid trans-(beta)-farnesene analogues and application thereof
  • Salicylic acid trans-(beta)-farnesene analogues and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Example 1: Preparation of 3-methoxysalicylic acid-(E)-3,7-dimethyl-2,6-octadienyl ester (I-10)

[0037] In a 100ml three-neck flask, add 2.18g 3-methoxysalicylic acid, 3.20g DCC, 1.74g DMAP and 20mL THF, add dropwise 2.00g geraniol, and react at 20°C for 3 hours. Extract with water three times, take the organic phase, remove the solvent under reduced pressure, and separate by silica gel column chromatography (eluent is petroleum ether:ethyl acetate V:V=500:1) to obtain yellow liquid 3-methoxysalicylic acid -(E)-3,7-dimethyl-2,6-octadienyl ester (I-10), yield 53.8%. 1H NMR: 11.10 (s, 1H, ArOH), 7.26-7.47 (m, 1H, ArH), 7.02-7.09 (m, 1H, ArH), 6.81 (t, 1H, J=8.07Hz, ArH), 5.43- 5.48(m,1H,=CH),5.08-5.10(m,1H,=CH),4.87(d,2H,J=7.14Hz,CH 2 ),3.90(s,3H,ArOCH 3 ),2.10-2.14(m,4H,CH 2 CH 2 ),1.80(s,3H,CH 3 ),1.75(s,3H,CH 3 ),1.60(s,3H,CH 3 ).

[0038] The target compounds numbered I-2~I-4, I-12~I-14, I-18~I-25 and I-27~I-38 were obtained by the same method.

Embodiment 2

[0039] Example 2: Preparation of 3-hydroxysalicylic acid-(E)-3,7-dimethyl-2,6-octadienyl ester (I-5)

[0040] Step 1: Preparation of acetonitrile 3-hydroxysalicylate (intermediate 1)

[0041] In a 100ml three-neck flask, add 0.50g of 3-hydroxysalicylic acid, 0.29g of chloroacetonitrile, 0.49g of triethylamine and 20mL of acetone, and react under reflux for 6 hours. CH 2 Cl 2 Extract with water three times, take the organic phase, remove the solvent under reduced pressure, and separate by silica gel column chromatography to obtain acetonitrile 3-hydroxysalicylate as a yellow oily liquid with a yield of 75%.

[0042] Step 2: Preparation of 3-hydroxysalicylic acid-(E)-3,7-dimethyl-2,6-octadienyl ester (I-5)

[0043] In a 100ml three-necked flask, add 2.00g of acetonitrile 3-hydroxysalicylate, 2.19g of potassium carbonate, 1.80g of geraniol and 40mL of N,N-dimethylformamide, and react at 90°C for 6 hours. Extracted with water, removed the solvent under reduced pressure, and se...

Embodiment 3

[0045] Example 3: Preparation of 3-methyl-2-benzyloxy-salicylic acid-(E)-3,7-dimethyl-2,6-octadienyl ester (I-7)

[0046] Step 1: Preparation of benzyl 3-methyl-2-benzyloxysalicylate (intermediate 2)

[0047] In a 100ml three-neck flask, add 2.00g of 3-methylsalicylic acid, 6.75g of benzyl bromide, 1.59g of tri-NaOH, 0.68g of TBAB and 15mL of CH 2 Cl 2 , 15mL of water, and react at room temperature for 4 hours. Wash with water three times, take the organic phase, remove the solvent under reduced pressure, and separate by silica gel column chromatography to obtain light yellow liquid benzyl 3-methyl-2-benzyloxysalicylate with a yield of 97%.

[0048] Step 2: Preparation of 3-methyl-2-benzyloxysalicylic acid (intermediate 3)

[0049] In a 100ml three-necked flask, 3.18g of benzyl 3-methyl-2-benzyloxysalicylate, 1.10g of NaOH, and 35mL of ethanol were added, and the mixture was refluxed for 4 hours. The solvent was removed under reduced pressure and acidified with dilute hydr...

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Abstract

The invention discloses salicylic acid trans-(beta)-farnesene analogues as well as a preparation method and an application thereof, and belongs to the field of organic compound synthesis. The compound as shown in a formula I in the specification is obtained by the following steps of: mixing salicylic acid and analogues of salicylic acid, geraniol, geranylamine or substituted geranylamine serving as raw materials with an organic solvent, carrying out condensation reaction to obtain the salicylic acid trans-(beta)-farnesene analogues with different substitutes, and carrying out silica-gel column chromatography separation and purification. The preparation method of the compound as shown in the formula I has the advantages of mild reaction, simple and easy operation, relatively high yield and relatively low cost; and the compound is more stable than trans-(beta)-farnesene. The compound as shown in the formula I has multiple biological activities, relatively good killing activity to aphids at high dose, warning repellant activity to aphids at low dose, tobacco mosaic virus resisting activity and bactericidal activity, can be used for pest control and disease prevention in the agricultural production, and has relatively high application and development value.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, and specifically relates to salicylic acid trans-(β)-farnesene analogues and a preparation method thereof, as well as the application of the compounds in aphid control, plant disease resistance and sterilization. Background technique [0002] Aphid alarm pheromone is the oily droplet secreted by the abdominal tube when aphids are attacked by natural enemies. It can make the surrounding aphids alarm, stop feeding, and quickly escape from the harm site, thereby stopping the damage to the host plant. Bowers and Edwards first isolated and identified the main component of aphid alarm pheromone in 1972 as (anti)-β-farnesene ((E)-β-farnesene, referred to as EBF. Francis et al. found that EBF is an aphid alarm pheromone There are even 12 species of aphids with EBF as the only component. The research results show that aphid alarm pheromones have multiple biological activities in addition to the w...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/92C07C69/84C07C67/08C07C67/03C07C205/60C07C201/12C07C235/60C07C231/02A01P7/04A01P1/00A01P3/00
CPCC07C67/03C07C67/08C07C69/84C07C69/92C07C201/12C07C205/60C07C231/02C07C235/60
Inventor 杨新玲秦耀果宋敦伦张景朋凌云谭晓庆曲焱焱李文浩
Owner CHINA AGRI UNIV
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