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Application of maleimide compound as chitin synthase inhibitor

A technology of maleimide and chitin synthase, which can be used in application, biocide, animal repellent, etc., can solve problems such as economic losses, achieve less toxic and side effects on human body, and cheap and easy-to-obtain raw materials , the effect of a simple synthesis method

Active Publication Date: 2020-06-23
杭州佳嘉乐生物技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, plant diseases caused by fungi have caused huge economic losses to the agriculture of various countries, and new high-efficiency and environmentally friendly antifungal drugs are an inevitable choice for the control of agricultural diseases

Method used

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  • Application of maleimide compound as chitin synthase inhibitor
  • Application of maleimide compound as chitin synthase inhibitor
  • Application of maleimide compound as chitin synthase inhibitor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Embodiment 1: the synthesis of N-phenyl-maleimide (I-A-1):

[0026]

[0027] Weigh 0.98g of maleic anhydride (II-1) and 0.93g of aniline (III-1) into a three-necked round-bottomed flask, add 15mL of acetone and react at room temperature for 1 hour to generate the corresponding maleamic acid. Add 5 mL of acetic anhydride and 100 mg of sodium acetate to the generated maleamic acid, then heat at reflux for 2-3 h. After the reaction finished, the reaction solution was cooled to room temperature, and the solvent was distilled off under reduced pressure to obtain a concentrated solution, which was separated by silica gel column chromatography (eluent V 石油醚 :V 乙酸乙酯 =8:1), and the target liquid was collected, the solvent was removed by vacuum rotation, and the target product N-phenyl-maleimide (I-A-1) was obtained by vacuum drying at 60°C.

[0028] Yield 78.6%, Purity 96.7%. 1 H NMR (500MHz, CDCl3) δ7.38-7.35(m, 2H), 7.35-7.31(m, 2H), 7.29(dq, J=3.9, 1.7Hz, 1H), 6.72(d, J...

Embodiment 2

[0029] Embodiment 2: the synthesis of N-benzyl-maleimide (I-A-2):

[0030]

[0031] In Example 1, the raw material aniline (Ⅲ-1) was changed to benzylamine (Ⅲ-2), and other operations were the same as in Example 1, and the feed ratio remained unchanged.

[0032] Yield 73.3%, Purity 97.9%. 1 H NMR (500MHz CDCl 3 )δ7.38-7.35(m,2H),7.35-7.31(m,2H),7.29(dq, J=3.9,1.7Hz,1H),6.72(d,J=5.0Hz,2H),4.69(s ,2H).HRMS[M+H] + :188.1985.

Embodiment 3

[0033] Embodiment 3: the synthesis of N-phenethyl-maleimide (I-A-3):

[0034]

[0035] In Example 1, the raw material aniline (III-1) was changed to phenethylamine (III-3), and other operations were the same as in Example 1, and the feed ratio remained unchanged.

[0036] Yield 77.2%, Purity 95.3%. 1 H NMR (500MHz, CDCl 3 )δ7.50-7.46(m,2H),7.29-7.24(m,2H),7.24-7.18(m,2H),7.16(s,1H),3.69-3.65(m,2H),2.86-2.82( m,2H).HRMS[M+H] + :202.0785.

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PUM

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Abstract

The invention discloses an application of a maleimide compound as shown in a formula I. In the formula I, R0 is phenyl, benzyl, phenethyl, phenylpropyl, p-fluorophenyl, p-chlorophenyl, p-bromophenyl,p-methoxyphenyl, p-methylphenyl or p-hydroxyphenyl, R1 is hydrogen, methyl, phenyl or chlorine; and R2 is hydrogen, methyl, phenyl or chlorine. The provided maleimide compound has a good inhibition effect on chitin synthase.

Description

technical field [0001] The invention relates to the application of maleimide compounds as chitin synthase inhibitors. [0002] technical background [0003] At present, plant diseases caused by fungi have caused huge economic losses to the agriculture of various countries, and new antifungal drugs with high efficiency and no pollution to the environment are the inevitable choice for controlling agricultural diseases. Chitin is an essential substance in the growth and development of common plant pathogenic fungi, and is also an important part of the fungal cell wall, and chitin does not exist in plants and mammals. If some small molecular compounds are used to inhibit the key enzymes in chitin biosynthesis, it can interfere with the metabolism of chitin in fungi, and it will not affect plants and mammals. Therefore, more and more scholars believe that Chitin metabolic processes may serve as targets for antifungal agents. Chitin synthase, as the key enzyme in the process of c...

Claims

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Application Information

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IPC IPC(8): A01N37/32A01P3/00A61K31/402A61P31/10
CPCA01N37/32A61K31/402A61P31/10
Inventor 陆跃乐张珂睿石小在包莹玲陈小龙范永仙
Owner 杭州佳嘉乐生物技术有限公司
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