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Long-chain alkyl salicylic compound as well as preparation method application thereof

A chain alkyl salicylic acid and alkyl salicylic acid technology, which is applied in the compound synthesis and pesticide fields, can solve the problems of target biological drug resistance increase, environmental pollution, use restriction, etc., and achieve a simple synthesis method, easy promotion, and low cost of use Effect

Inactive Publication Date: 2011-04-13
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Sodium pentachlorophenate has been used in many countries. It has a good molluscicide effect, but it has broad-spectrum toxicity to non-target organisms, especially fish and shrimp farming, and causes serious environmental pollution. It has long been listed as a banned product by the international community
Niclosamide (Niclosamidum) has a good molluscicide effect and is the only molluscicide recommended by WHO, but it is expensive and toxic to aquatic organisms such as fish, and it can also lead to increased drug resistance of target organisms, making it in Use in developing countries is very limited

Method used

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  • Long-chain alkyl salicylic compound as well as preparation method application thereof
  • Long-chain alkyl salicylic compound as well as preparation method application thereof
  • Long-chain alkyl salicylic compound as well as preparation method application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Embodiment 1 synthetic hydrocarbyl salicylic acid compound

[0029] (1). Synthesis of methyl 2-hydroxy-4-methylbenzoate

[0030] 3.5g of 2-hydroxy-4-methylbenzoic acid (21.1mmol) was dissolved in 60mL of methanol, placed in an ice bath, and 12mL of concentrated sulfuric acid was slowly added dropwise. Then the water bath was heated to reflux overnight. Pour into ice water after cooling, extract 100mL x 2 times with dichloromethane, combine the organic layers, and saturated NaHCO 3 Wash the organic layer with anhydrous MgSO 4 After dehydration and concentration, 3.01 g (86%) of light yellow oil was obtained.

[0031]

[0032] (2). Synthesis of methyl 2-acetoxy-4-methylbenzoate

[0033] Add 3g of methyl 2-hydroxy-4-methylbenzoate (18.1mmol) into 8mL of acetic anhydride (8mmol), then add 8 drops of concentrated sulfuric acid dropwise, shake fully, keep in a water bath at 70°C for 10min, and shake occasionally. After cooling down slightly, pour into ice water, extra...

Embodiment 2

[0047] Example 2 Determination of the Activity of Hydrocarbyl Salicylate Compounds with Different Substitution Positions and Carbon Chain Lengths to Kill Oncomelania

[0048] Take 3-, 4-, 5-substituted hydrocarbyl salicylic acid respectively, and the compound whose carbon chain length is 9-13 is an example, and the selected three kinds of different hydrocarbyl salicylic acids are respectively 3-(1-tridecane En)salicylic acid (1), 4-(1-undecene)salicylic acid (2) and 5-(1-nonacene)salicylic acid (3) were synthesized by the above-mentioned method, and the purity was >95% %. In addition, 3-methylsalicylic acid (4), 4-methylsalicylic acid (5) and 5-methylsalicylic acid (6) were used as active references, and the wettability of niclosamide ethanolamine (Nic) The powder is the positive control drug.

[0049] The above monomers were dissolved with a small amount of absolute ethanol (final concentration <0.5%), and then diluted with dechlorinated water to different concentrations: 5...

Embodiment 3

[0058] Embodiment 3 prepares hydrocarbyl salicylic acid microemulsion

[0059] Take 10g of each hydrocarbyl salicylic acid monomer compound prepared above, put it in a 50ml Erlenmeyer flask, dissolve it with an appropriate amount of absolute ethanol, add 10ml of PEG400 and 20ml of water respectively, put it on a magnetic stirrer, stir evenly, and place it on a water bath at 56°C. Use isopropanol placed in a graduated burette to drop the prepared solution until it becomes clear, record the amount of isopropanol consumed, then dilute it with an appropriate amount of water to form a 10% microemulsion, and dilute it with water to a suitable concentration before use.

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Abstract

The invention belongs to the fields of compound synthesis and pesticides, in particular to a long-chain alkyl salicylic compound as well as a preparation method and application thereof in molluscicide preparation. Easily obtained raw materials and a simple synthetic method with low cost are adopted in the invention to synthesize the target compound. Proved by molluscicide test and shown by results, the LC50 value of the synthetic compound for killing oncomelania is within the oncomelania-killing activity range (smaller than 400 mg / L) of the molluscicide, which is required by the WTO (World Trade Organization). The compound of the invention can be singly used as the molluscicide or be used together with other molluscicides, can be further compounded with different accessories to prepare microemulsion, emulsion, powder and water agent or compounded with niclosamide, copper ion and other accessories to prepare a composite molluscicides to enhance the oncomelania killing effect, lessen the toxic and side effects and decrease the cost.

Description

technical field [0001] The invention belongs to the field of compound synthesis and pesticides, and relates to a hydrocarbyl salicylic acid compound, a preparation method thereof and an application in preparation of oncomelania preparations. Background technique [0002] The prior art discloses 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. Epidemiology believes that eradicating snails can cut off the transmission route of schistosomiasis. Therefore, killing snails is an internationally recognized important measure to prevent schistosomiasis. [0003] Surveys show that schistosomiasis is prevalent in temperate, subtropical, and tr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C65/05C07C65/19C07C51/353A01N37/40A01N59/20A01N25/04A01P9/00
Inventor 俞培忠毛佐华潘家祜谢程姜庆五
Owner FUDAN UNIV
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