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Non-peptide juvenile hormone synthetic inhibitor

A juvenile hormone and inhibitor technology, which is applied in the field of non-peptide juvenile hormone synthesis inhibitors, can solve the problems of complex structure, unsuitability for development and high synthesis cost, and achieves low cost, good development and application prospects, and novel structure. Effect

Inactive Publication Date: 2011-06-15
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are still the following disadvantages: the structure of the compound is complex (simulating the active peptide above pentapeptide), some structures are even more complex than natural peptides, and the synthesis cost is high, so it is not suitable for development as a new pesticide.

Method used

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  • Non-peptide juvenile hormone synthetic inhibitor
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  • Non-peptide juvenile hormone synthetic inhibitor

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1、A1

[0027] The synthesis of preparation embodiment 1, A1 compound

[0028] (1) Synthesis of non-peptide fragment 1: Add ethylenediamine (1 times the amount) dropwise into an ethanol solution of benzaldehyde (2.2 times the amount), stir at room temperature for 20 minutes, then add sodium borohydride ( 2.2 times the amount), slowly warming up to room temperature. Water and dichloromethane were added to the reaction solution, and the organic layer was extracted and dried. The dried substance was dissolved in dichloromethane, succinic anhydride (2.2 times the amount) was added and stirred at room temperature overnight, and the non-peptide fragment 1 was obtained by filtration and purification. The specific structural formula is:

[0029]

[0030] (2) Resin activation: Weigh 200 mg Rink Amide-AM resin, swell and activate it with 15 ml DCM for 3 h, add 20% piperidine DMF solution to cut for 20 min, and monitor the reaction with Kaiser’s reagent.

[0031] (3) Connecting to Leu: add...

preparation Embodiment 2、A2

[0037] The synthesis of preparation embodiment 2, A2 compound

[0038] (1) Synthesis of non-peptide fragment 1: Add ethylenediamine (1 times the amount) dropwise into an ethanol solution of benzaldehyde (2.2 times the amount), stir at room temperature for 20 minutes, then add sodium borohydride ( 2.2 times the amount), slowly warming up to room temperature. Water and dichloromethane were added to the reaction solution, and the organic layer was extracted and dried. The dried substance was dissolved in dichloromethane, succinic anhydride (2.2 times the amount) was added and stirred at room temperature overnight, and the non-peptide fragment 1 was obtained by filtration and purification. The structural formula of non-peptide fragment 1 is:

[0039]

[0040] (2) Resin activation: Weigh 200 mg Rink Amide-AM resin, swell and activate it with 15 ml DCM for 3 h, add 20% piperidine DMF solution to cut for 20 min, and monitor the reaction with Kaiser’s reagent.

[0041] (3) Conne...

preparation Embodiment 3、A3

[0045] The synthesis of preparation embodiment 3, A3 compound

[0046] (1) Synthesis of non-peptide fragment 2: 1,4-butanediamine (1 times the amount) was dropped into the ethanol solution of benzaldehyde (2.2 times the amount), stirred at room temperature for 20 minutes, and then added in batches when cooled to 0 degrees Sodium borohydride (2.2 times the amount), slowly warming up to room temperature. Water and dichloromethane were added to the reaction solution, and the organic layer was extracted and dried. The dried substance was dissolved in dichloromethane, succinic anhydride (2.2 times the amount) was added and stirred at room temperature overnight, and the non-peptide fragment 2 was obtained by filtration and purification. The structural formula of non-peptide fragment 2 is:

[0047]

[0048] (2) Resin activation: Weigh 200 mg Rink Amide-AM resin, swell and activate it with 15 ml DCM for 3 h, add 20% piperidine DMF solution to cut for 20 min, and monitor the react...

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Abstract

The invention discloses a non-peptide juvenile hormone synthetic inhibitor and belongs to the technical field of juvenile hormone synthetic inhibitors. A structural formula of an analogue is shown as a formula A. The non-peptide juvenile hormone synthetic inhibitor with a novel structure, simpleness, low cost and high activity of inhibiting juvenile hormone synthetic separation is obtained by substituting non-peptide micromolecule segments for amino acids in a core pentapeptide except for leucine. The compound of the formula A accords with the characteristics of an insect growth regulator andhas a good development application prospect.

Description

technical field [0001] The invention belongs to the technical field of juvenile hormone synthesis inhibitors, in particular to a class of non-peptide juvenile hormone synthesis inhibitors. Background technique [0002] Juvenile hormone (JH) is an important class of insect hormones. It regulates the growth and development of immature insects and the reproduction of adults. Scientists have developed a large series of insect growth regulators (IGRs) - juvenile hormone analogues by using JH as the lead. The main varieties of existing juvenile hormone analogues are: methoprene, triprene, hydroprene, kinoprene, fenoxycard, Pyriproxyfen (pyriproxyfen) and pyridoxone (NC-170) and so on. These commercialized pesticides have played an important role in integrated pest management. However, these pesticides are all juvenile hormone analogs in chemical structure, and there is a possibility of cross-resistance. Therefore, it is very necessary to research and develop other IGRs with n...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C237/22C07C231/02C07D249/18A01N37/46A01N43/647A01P23/00
Inventor 杨新玲谢勇凌云吴小庆斯蒂芬·陶博邓希乐张莉陈馥衡
Owner CHINA AGRI UNIV
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