Trichodermin C8 oxime ether derivatives and application thereof

A technology of trichodermain and carbonyl trichodermain, applied in biocides, chemicals for biological control, applications, etc.

Inactive Publication Date: 2014-01-22
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, most of the existing new varieties of fungicides in my country are protected by foreign patents, and the use of old varieties is also affected by resistance problems.

Method used

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  • Trichodermin C8 oxime ether derivatives and application thereof
  • Trichodermin C8 oxime ether derivatives and application thereof
  • Trichodermin C8 oxime ether derivatives and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0085] The synthetic method of embodiment 1, compound III, its reaction formula is:

[0086]

[0087] Concrete reaction process is as follows:

[0088] Add 0.1g of 8-carbonyltrichomycin (II), 3 equivalent molar amounts of hydroxylamine hydrochloride and 5mL of anhydrous methanol to the reaction flask, and add 3 equivalent molar amounts of potassium carbonate aqueous solution ( The mass concentration is 15-25%), and the reaction process is detected by TLC. After 5 hours, the reaction was completed. The reaction liquid was concentrated to dryness in vacuo and washed 3 times with 5% (volume concentration) dilute hydrochloric acid, 5 mL each time, and then extracted 3 times with dichloromethane (5 mL each time), and the obtained organic phase was used Anhydrous Na 2 SO 4 Drying, concentration and precipitation of white crystals, yield 88.5%.

[0089] Structural data of compound III: 1 H-NMR (500MHz, CDCl 3 ):δ8.57(s,1H,H-OH),5.88-5.84(dd,J 1 =J 2 =1.0Hz,1H,H-10),4.31-4....

Embodiment 2

[0091] Embodiment 2, the synthetic general method of compound IV, its reaction formula is as follows:

[0092]

[0093] Concrete reaction process is as follows:

[0094] Add 0.5g of trans-8-hydroxyiminotrichodermain (compound of formula III), 1.5 equivalent molar amounts of sodium hydride and 10mL of N,N-dimethylformamide into the reaction bottle, ℃) After reacting for 15 minutes, add 1.5 equivalent molar amounts of iodoalkanes (methyl iodide, ethyl iodide, propane iodide, pentyl iodide, etc.) dropwise, stir the reaction at room temperature, and detect the reaction progress by TLC. After the reaction (about 4 hours), the reaction solution was extracted three times with ethyl acetate (the amount of ethyl acetate each time was 8ml), and the obtained organic phase (located in the upper layer) was washed with water three times (the amount of water each time was 6ml), Anhydrous Na 2 SO 4 Dry and concentrate. Then, it was separated by silica gel column chromatography (using a...

Embodiment 3

[0102] Embodiment 3, a kind of synthesis method of Trichoderma C8 oxime ether derivative (A-2), its reaction formula is:

[0103]

[0104] Concrete reaction process is as follows:

[0105] Add the compound IV-1 (0.3mol) obtained by the method of Example 2, 2 equivalent molar amounts of propionic acid, 20mL CH 2 Cl 2 , adding 1 equivalent molar amount of 4-dimethylaminopyridine (DMAP) and 3 equivalent molar amounts of dicyclohexylcarbodiimide (DCC), stirring the reaction at room temperature, and detecting the reaction progress by TLC. After the reaction (about 12 hours), the reaction solution was washed three times with dilute hydrochloric acid (the volume concentration of dilute hydrochloric acid is 5%, and the dosage of each washing is 5ml), washed three times with water (the dosage of each washing is 5ml), Anhydrous Na 2 SO 4 Dry and concentrate. Then it was separated by silica gel column chromatography (eluent: ethyl acetate:petroleum ether=1:10, volume ratio) to ob...

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Abstract

The invention belongs to the field of bactericide preparation, and relates to a series of trichodermin C8 oxime ether derivatives with bacteriostatic activity on plant pathogenic fungi. Specifically, the invention discloses trichodermin C8 oxime ether derivatives, and the structural general formula of the trichodermin C8 oxime ether derivatives is shown in the specification. The invention also discloses a preparation method of the trichodermin C8 oxime ether derivatives. In the trichodermin C8 oxime ether derivatives, the oxime ether structure is used as an efficient molecular efficacy group, and the parent structure of trichodermin is subjected to functional group transformation so as to prepare a series of trichodermin C8 oxime ether derivatives. The trichodermin C8 oxime ether derivatives can be used as a bactericide for the agriculture and gardening to suppress the plant pathogenic fungi.

Description

technical field [0001] The invention belongs to the field of fungicide creation of new pesticide creation, and specifically relates to a series of trichodermain C8 oxime ether derivatives with antibacterial activity against plant pathogenic fungi. The invention also provides agricultural and horticultural methods of using these compounds and corresponding compositions thereof, as well as methods of preparing them. Background technique [0002] According to the national "Eleventh Five-Year" development plan, pesticide innovation and creation is the key research content. At present, the discovery of new pesticides or lead compounds is still mainly based on analogous synthesis and natural substance models. [0003] Among them, biogenic pesticides, as a category of natural active substances, are an important way to create new pesticides. Because of its low toxicity to humans and animals, good environmental compatibility, and the resistance of harmful organisms, it meets the re...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/10A01N43/90A01P3/00
CPCA01N43/90C07D493/10
Inventor 赵金浩程敬丽郑敏黎小亮章初龙王国平林福呈
Owner ZHEJIANG UNIV
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