Synthesis and application of capsaicin halogenated derivative

A technology of reactions and compounds, applied in the field of chemistry, can solve problems such as high price and limited supply

Active Publication Date: 2018-09-07
SHANGHAI NATURE STANDARD R&D & BIOTECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the production cost of natural capsaicin is lower than that of synthetic products, it is still expensive and limited in supply, so it still has great limitations as a botanical insecticide

Method used

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  • Synthesis and application of capsaicin halogenated derivative
  • Synthesis and application of capsaicin halogenated derivative
  • Synthesis and application of capsaicin halogenated derivative

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0046] The preparation of compound as described in general formula (I) comprises the following steps:

[0047]

[0048] 3-Chloro-5-fluorobenzylamine reacts with formula (II) compound acid chloride to obtain formula (I) compound, and the molar ratio of 3-chloro-5-fluorobenzylamine and formula (II) compound acid chloride is 1:1.1-1.5 , R is C 1-9 Alkyl, halogen substituted C 1-9 Alkyl, C 1-9 Alkenyl, halogen substituted C 1-9 Alkenyl.

[0049] The preparation of the compound described in general formula (I) has one or more features selected from the following:

[0050] (i) the 3-chloro-5-fluorobenzylamine is reacted with the compound acid chloride of formula (II) in an organic solvent, and the organic solvent is selected from the group consisting of dichloromethane, tetrahydrofuran or pyridine;

[0051] (ii) the reaction is carried out in the presence of a base, and the base is selected from the group consisting of triethylamine, pyridine;

[0052] The reaction of (iii)...

Embodiment 1

[0073] Synthesis of N-(3-chloro-5-fluorobenzyl)octylamide

[0074]

[0075] Weigh 159mg of 3-chloro-5-fluorobenzylamine (1mmol) into a dry 50mL eggplant-shaped reaction bottle, add 15mL of dichloromethane, stir until the substrate is completely dissolved, add 200μL of triethylamine and heat at 0~5℃ A solution of 194 mg octanoyl chloride (1.2 mmol dissolved in an appropriate amount of dry dichloromethane) was slowly added dropwise in an ice bath. After the dropwise addition was completed, the mixture was followed and monitored by TLC at room temperature. When the raw material point disappeared, it was washed three times with 20 mL of saturated sodium bicarbonate, water and saturated NaCl aqueous solution, and dried over anhydrous sodium sulfate. After rotary evaporation under reduced pressure, silica gel column chromatography separated to obtain N-(3-chloro-5-fluorobenzyl)octylamide. 1 H NMR (CDCl 3 , 500MHz), δ: 8.19 (1H, s, -NH), 7.62 (1H, d, J = 2.0Hz), 7.32 (1H, s), 6....

Embodiment 2

[0077] Synthesis of 4-chloro-N-(3-chloro-5-fluorobenzyl)butanamide

[0078]

[0079] Weigh 159mg of 3-chloro-5-fluorobenzylamine (1mmol) into a dry 50mL eggplant-shaped reaction bottle, add 15mL of dichloromethane, stir until the substrate is completely dissolved, add 200μL of triethylamine and heat at 0~5℃ A solution of 168 mg of chlorobutyryl chloride (1.2 mmol dissolved in an appropriate amount of dry dichloromethane) was slowly added dropwise in an ice bath. After the dropwise addition was completed, the mixture was followed and monitored by TLC at room temperature. When the raw material point disappeared, it was washed three times with 20 mL of saturated sodium bicarbonate, water and saturated NaCl aqueous solution, and dried over anhydrous sodium sulfate. After rotary evaporation under reduced pressure, it was separated by silica gel column chromatography to obtain the synthesis of 4-chloro-N-(3-chloro-5-fluorobenzyl)butyramide. 1 H NMR (CDCl 3 , 500MHz), δ: 8.19 (1...

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Abstract

The invention relates to synthesis and application of a capsaicin halogenated derivative. The capsaicin halogenated derivative has a structural formula I as shown in the description; in the formula, Ris C1-9 alkyl, halogenated C1-9 alkyl, C1-9 alkenyl and halogenated C1-9 alkenyl. The invention further relates to an agricultural composition with the compound or an agricultural pharmacological acceptable salt. By adopting the compound and the agricultural composition provided by the invention, injurious insects can be effectively killed and / or prevented.

Description

technical field [0001] The invention relates to the technical field of chemistry, in particular to the synthesis and application of a capsaicin halogenated derivative. Background technique [0002] Capsaicin is a kind of pungent and irritating vanillyl amide alkaloid in capsicum. It is composed of various homologues, and its main active ingredients are capsaicin and dihydrocapsaicin. Capsaicin has various biological activities such as analgesic and anti-inflammatory, anti-cancer, blood lipid regulation, weight loss, anti-fatigue, insecticidal and antibacterial, and has a wide range of uses in the fields of medicine and pesticides. In the field of pesticides, Chinese scholars have found that capsaicin has strong toxicity and good control effect on peach aphid, and shows strong oviposition avoidance and antifeeding activity on diamondback moth. The compound preparation of capsaicin and nicotine is The field has a good control effect on diamondback moth and aphids. [0003] T...

Claims

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Application Information

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IPC IPC(8): C07C233/13C07C231/02A01N37/18A01P7/04
CPCA01N37/18C07C233/13
Inventor 钱勇辛振强舒亚平张田勇谢天培
Owner SHANGHAI NATURE STANDARD R&D & BIOTECH
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