Long-chain alkyl salicylic acid and application thereof in preparing oncomelania killing preparation

A technology for long-chain alkyl salicylic acid and alkyl salicylic acid, which is applied in the field of pesticides and can solve the problems of increased drug resistance, high price, toxicity and the like of target organisms

Inactive Publication Date: 2015-12-30
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] So far, the use of chemically synthesized molluscicides is the main means of controlling molluscs, but there are also various defects. Among them, such as sodium pentachlorophenate, which has been used by many countries and has a good molluscicide effect, but it is not effective for non-target organisms, especially Fish and shrimp farming has broad-spectrum toxicity and is likely to cause serious environmental pollution. It has been listed as a banned product by relevant international organizations; However, its high price and toxicity to fish and other aquatic organisms greatly restrict its use in developing countries, and it can also lead to increased drug resistance of target organisms, etc.

Method used

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  • Long-chain alkyl salicylic acid and application thereof in preparing oncomelania killing preparation
  • Long-chain alkyl salicylic acid and application thereof in preparing oncomelania killing preparation
  • Long-chain alkyl salicylic acid and application thereof in preparing oncomelania killing preparation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1 Preparation of 2-acetoxy-4-(1-alkyl) methyl benzoate

[0026] 2-Acetoxy-4-(1-enyl) methyl benzoate cis-trans isomer crude product (according to patent CN102010328A synthesis method) is dissolved in acetic acid, and 10% Pd / C of 10% molar weight is added in the solution . Mixed solution room temperature, 60psi with H 2 Rocking reaction 9 ~ 11h. After filtration, the filtrate was poured into water and extracted three times with ethyl acetate. The organic layer was washed with water and saturated brine, respectively, and then washed with Na 2 SO 4 Dry and concentrate under reduced pressure to obtain the crude product. The crude product is subjected to column chromatography (stationary phase is: SilicaGelH mixed uniformly and AgNO with a weight ratio of 1% to 2%. 3 ; The mobile phase was: petroleum ether: ethyl acetate = 50:1) to obtain a pale yellow oil.

Embodiment 2

[0027] Example 2. Preparation of 2-hydroxyl-4-(1-heptyl)benzoic acid

[0028] Methyl 2-acetoxy-4-(1-heptyl)benzoate (88.7 mg, 0.30 mmol) was dissolved in 2.1 mL of ethanol, and 1 mol / L NaOH (0.91 mL, 0.91 mmol) was added dropwise with stirring. The water bath was refluxed for 5h, then the solvent was evaporated, adjusted to PH=3 with 1mol / L HCl, then 5mL of water was added, CH 2 Cl 2 Extract 5mL×3 times, combine the organic layers, anhydrous Na 2 SO 4 Dehydrated and concentrated to give a light yellow powder (67.4mg, 94%). 1 H-NMR (CDCl 3 ,400MHz)δ0.87(t,J=6.5Hz,3H),1.26(m,8H),1.60(m,2H),2.59(t,J=7.4,2H),6.75(d,J=8.3Hz ,1H),6.81(brs,1H),7.80(d,J=8.3Hz,1H),10.41(brs,1H); HRESIMSfound:235.1298.Calcd:235.1334forC 14 h 19 o 3 ([M-H] - ).

Embodiment 3

[0029] Example 3. Preparation of 2-hydroxyl-4-(1-decyl)benzoic acid

[0030] Methyl 2-acetoxy-4-(1-decyl)benzoate (106.8 mg, 0.32 mmol) was dissolved in 2.2 mL of ethanol, and 1 mol / L NaOH (0.96 mL, 0.96 mmol) was added dropwise with stirring. The water bath was refluxed for 6h, then the solvent was evaporated, adjusted to PH=3 with 1mol / L HCl, then 6mL of water was added, CH 2 Cl 2 Extract 6mL×3 times, combine organic layers, anhydrous Na 2 SO 4 Dehydrated and concentrated to give a white powder (80.9 mg, 91%). 1 H-NMR (CDCl 3 ,400MHz)δ0.87(t,J=6.5Hz,3H),1.26(m,14H),1.59(m,2H),2.59(t,J=7.4,2H),6.75(dd,J=8.1Hz ,1.2Hz,1H),6.81(brs,1H),7.80(d,J=8.1Hz,1H),10.41(brs,1H); HRESIMSfound:279.0930.Calcd:279.1955forC 17 h 27 o 3 ([M+H] + ).

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Abstract

The invention belongs to the technical field of pesticides, and relates to long-chain alkyl salicylic acid and application thereof in preparing an oncomelania killing preparation. 6-alkyl salicylic acid, 3-alkyl salicylic acid, 4-alkyl salicylic acid and 5-alkyl salicylic acid are used as starting materials, the raw materials are compounded to obtain a long-chain alkyl substituted salicylic acid compound with the side chain being saturated alkyl through corresponding methyl salicylic acid. The salicylic acid compound can be used for preparing a single or compound oncomelania killing preparation; compared with olefin with double bonds, the chemical stability is better, and the oncomelania killing activity is higher.

Description

technical field [0001] The invention belongs to the technical field of pesticides, and relates to long-chain alkyl salicylic acid and its use in preparing oncomelania killing preparations. The salicylic acid compound can be used to prepare single or compound molluscicides. Background technique [0002] Studies have reported that oncomelania is the only intermediate host for the transmission of schistosomiasis. The miracidia of schistosomiasis can develop into schistosomiasis after invading the snail, which multiplies tens of thousands of times in the snail, and continuously produces cercariae in the water or on the wet soil surface, so as to infect humans and other animals. The spread and spread of the disease. Killing snails can cut off the transmission route of schistosomiasis, so killing snails is an internationally recognized important measure to prevent schistosomiasis. [0003] Schistosomiasis is prevalent in temperate, subtropical, and tropical regions. In 2001, W...

Claims

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Application Information

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IPC IPC(8): C07C65/05C07C51/353A01N37/40A01P9/00
Inventor 俞培忠毛佐华潘家祜杨宗龙王秀艳吕远
Owner FUDAN UNIV
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