Novel composite phosphonium salt as well as preparation method and antibacterial application thereof

A quaternary phosphonium salt, a new type of technology, applied in the field of fine chemical synthesis, can solve the problems of poor stability, unsatisfactory effect, and short duration of inhibition, and achieve the effects of good stability, low synthesis price, and less raw material consumption

Active Publication Date: 2016-02-17
SOUTH CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Although the existing quaternary phosphonium salt fungicides have the advantages of fast antibacterial action, wide antibacterial spectrum, and good anti-mildew effect, they still have certain defects, such as poor stability, unsatisfactory effect, and short duration of inhibitory action.

Method used

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  • Novel composite phosphonium salt as well as preparation method and antibacterial application thereof
  • Novel composite phosphonium salt as well as preparation method and antibacterial application thereof
  • Novel composite phosphonium salt as well as preparation method and antibacterial application thereof

Examples

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Comparison scheme
Effect test

Embodiment 1

[0027] A compound quaternary phosphonium salt A in a single crystal form has the molecular structure shown in the above general formula, wherein R is Cl.

[0028] Its preparation method is as follows:

[0029] (1) Dissolve 2mmol of 2-chlorobenzyl bromide and 1.6mmol of triphenylphosphine in 20mL of acetone, stir and reflux at 65-70oC for 24 hours, during which a white precipitate is formed, after natural cooling, suction filter, and use A small amount of acetone and ether washed the filter cake to remove impurities and accelerate drying, and then vacuum-dried to obtain 2-chlorobenzyltriphenylphosphine bromide with a yield of 79.3%; infrared spectroscopic analysis: IR (cm -1 ): ν(benzene ring C–H): 3053; ν(CH 2 ): 2925, 2884; ν(C=C): 1587, 1432; ν(C–P): 1111;

[0030] (2) 1 mmol of 2-chlorobenzyltriphenylphosphine bromide and CuCl 2 2H 2 0.45mmol was dissolved in 15mL of methanol, then 0.5mL of hydrochloric acid was added, stirring was continued, while heating to reflux for...

Embodiment 2

[0038] A compound quaternary phosphonium salt B in a single crystal form has the molecular structure shown in the above general formula, wherein R is Br.

[0039] Its preparation method is as follows:

[0040] (1) Dissolve 2mmol of 2-bromobenzyl bromide and 2mmol of triphenylphosphine in 30mL of acetone, stir and reflux at 65-70oC for 20 hours, during which a white precipitate is formed, after natural cooling, carry out suction filtration, and use a small amount of Acetone and ether wash the filter cake to remove impurities and accelerate drying, and then vacuum-dry to obtain 2-bromobenzyltriphenylphosphine bromide with a yield of 86.4%; infrared spectroscopic analysis: IR (cm -1 ): ν(benzene ring C–H): 3053; ν(CH 3 ): 2922, 2884; ν(C=C): 1584, 1432; ν(C–P): 1114;

[0041] (2) 1mmol of the obtained 2-bromobenzyltriphenylphosphine bromide and CuCl 2 2H 2 0.5mmol was dissolved in 20mL of methanol, then 1mL of hydrochloric acid was added, stirring continued, while heating to ...

Embodiment 3

[0043] A compound quaternary phosphonium salt C in a single crystal form has the molecular structure shown in the above general formula, wherein R is NO 2 .

[0044] Its preparation method is as follows:

[0045](1) Dissolve 2mmol of 2-nitrobenzyl bromide and 2.4mmol of triphenylphosphine in 40mL of acetone, stir and reflux at 65-70oC for 16 hours, during which a white precipitate is formed, after natural cooling, suction filter, and use A small amount of acetone and ether washed the filter cake to remove impurities and accelerate drying, and then vacuum-dried to obtain 2-nitrobenzyltriphenylphosphine bromide with a yield of 88.6%; infrared spectroscopic analysis: IR (cm -1 ):ν(NH 2 ): 3341; ν(benzene ring C–H): 3050; ν(CH 2 ): 2922, 2875; ν(C=C): 1581, 1432; ν(NO 2 ): 1530, 1335; ν(C–P): 1105.

[0046] (2) 1mmol of the obtained 2-nitrobenzyltriphenylphosphine bromide and CuCl 2 2H 2 O0.56mmol was dissolved in 25mL of methanol, then 1.5mL of hydrochloric acid was added,...

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Abstract

The invention belongs to the technical field of fine chemical synthesis and particularly relates to a novel composite phosphonium salt as well as a preparation method and an antibacterial application thereof. The novel composite phosphonium salt adopts a molecular structure shown in the general formula represented in the specification, wherein R is selected from one of Cl, Br and NO2 groups. The novel composite phosphonium salt has good stability, excellent antibacterial performance and long bacteriostasis duration; the preparation method comprises steps of synthesis of brominated substituted benzyl triphenylphosphine, synthesis of an antibacterial complex, crystallization and the like, the operation is simple and controllable, large-scale instruments and equipment are not required, and the production cost is reduced remarkably.

Description

technical field [0001] The invention belongs to the technical field of fine chemical synthesis, and in particular relates to a novel composite quaternary phosphonium salt, a preparation method thereof and an antibacterial application. Background technique [0002] Antibacterial agents refer to various preparations that can kill or inhibit the activity of microorganisms within a certain period of time. They are chemical substances that are highly sensitive to microorganisms such as bacteria and molds. Antimicrobial agents have a wide range of uses, are closely related to human life, and are widely used in industry, agriculture, and animal and plant protection. The quaternary phosphonium salt was discovered in the early 1990s as a water treatment agent. In 1990, Gramham pointed out that the quaternary phosphonium salt was used for industrial and oilfield water treatment with high efficiency, fast, broad spectrum, and low environmental and fish effects. It has the advantages o...

Claims

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Application Information

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IPC IPC(8): A01N57/22A01N59/20C07F9/54A01P3/00A01P1/00
Inventor 倪春林周家容叶辉青张正胡甜刘茵满丽敏
Owner SOUTH CHINA AGRI UNIV
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