CN102669110A - Application of indole diketopiperazine derivatives - Google Patents
Application of indole diketopiperazine derivatives Download PDFInfo
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- CN102669110A CN102669110A CN2012101510801A CN201210151080A CN102669110A CN 102669110 A CN102669110 A CN 102669110A CN 2012101510801 A CN2012101510801 A CN 2012101510801A CN 201210151080 A CN201210151080 A CN 201210151080A CN 102669110 A CN102669110 A CN 102669110A
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- diketopiperazine derivatives
- piperazine derivative
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- WJXLEDRXFLAJJG-DEOSSOPVSA-N CC(C)(C=C)c1c(C[C@@H](C(NC2=C)=O)NC2=O)c(cc(CC=C(C)C)cc2CC=C(C)C)c2[nH]1 Chemical compound CC(C)(C=C)c1c(C[C@@H](C(NC2=C)=O)NC2=O)c(cc(CC=C(C)C)cc2CC=C(C)C)c2[nH]1 WJXLEDRXFLAJJG-DEOSSOPVSA-N 0.000 description 1
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Abstract
The invention relates to microbial source pesticide, in particular to an application of indole diketopiperazine derivatives. The indole diketopiperazine derivatives can be used for preparing agricultural insecticide and are shown as a formula (1) or a formula (2). The indole diketopiperazine derivatives related by the invention are used as microbial source natural products, only contain four kinds of elements including carbon, hydrogen, oxygen and nitrogen, can be easily degraded in environment and have small influence on non-target organisms, particularly on natural enemy of pests and beneficial microorganisms. The formula (1) and the formula (2) are shown in the accompanying drawing.
Description
Technical field
The present invention relates to microbe-derived insecticide, a kind of specifically application of indole dione piperazine derivative.
Background technology
Estimate that according to the FAO of the World Food Programme the grain loss that annual in the world due to illness insect pest causes is about 20%, it is about 30% that cotton loses, the loss of fruit tree, vegetables about 20%.Therefore, how more efficiently controlling plant diseases has become the task of top priority.In numerous means of prevention, chemical pesticide control is being taken on extremely important role.But along with a large amount of uses of chemical pesticide, plant pest is also more and more obvious to its pesticide resistance, has also brought environmental pollution, person poultry poisoning and three to cause problems such as (carcinogenic, teratogenesis, mutagenesis) thereupon.Compare with traditional chemical synthetic pesticide, biogenic pesticide has following advantage: (1) is lower to mammalian toxicity mostly, and is safer to people and animals in the use; (2) control spectrum is narrower, and selectivity is obvious; (3) little to environmental pressure, safer to non-target organism.So the exploitation of biogenic pesticide has great importance with the sustainable development of using human health, environmental protection and agricultural.
Summary of the invention
The object of the present invention is to provide a kind of application of indole dione piperazine derivative.
For realizing above-mentioned purpose, the technical scheme that the present invention adopted is:
A kind of application of indole dione piperazine derivative, the indole dione piperazine derivative can be used for preparing agricultural insecticide; Said indole dione piperazine derivative is shown in formula () or the formula (two);
Formula (one) formula (two).
Said insecticide formulation can be prepared into liquid, sustained release agent or powder.
The advantage that the present invention had:
1) indole dione piperazine compounds involved in the present invention is separated and obtains through fermented and cultured, extraction by the diffusing capsule bacterium (Eurotium cristatum) of coronoid process; And having the deadly activity of better halogen worm, compound tetradehydroechinulin (formula one) and didehydroechinulin (formula two) are to the LD of halogen worm
50Value is respectively 19.8 and 27.1 μ g/mL.
2) indole dione piperazine derivative involved in the present invention can be used as novel pesticide composition or the lead compound with insecticidal action.
Characteristics such as indole dione piperazine derivative 3) involved in the present invention can utilize microorganism to carry out the scale fermentation, and it is simple to have production technology, and the cycle is short, product cost is low.
4) indole dione piperazine derivative involved in the present invention only contains carbon, hydrogen, oxygen, 4 kinds of elements of nitrogen as microbe-derived natural products, in environment, is easy to degraded, and to non-target organism, particularly the influence of pest natural enemy and beneficial microbe is less;
Embodiment
For illustrating understanding, the present invention is done further elaboration below in conjunction with some non-limiting embodiments to characteristic of the present invention.
Embodiment 1:
The indole dione piperazine derivative is the indole dione piperazine derivative shown in formula () or the formula (two); The compound of its formula () and formula (two) is respectively tetradehydroechinulin and didehydroechinulin, is indole dione piperazines known compound.
Formula (one) formula (two)
Wherein, The preparation process of indole dione piperazines known compound tetradehydroechinulin (formula one) and didehydroechinulin (formula two) can be respectively referring to document Helv.Chim.Acta, 2012,95; 163-168 and Helv.Chim.Acta; 2010,93, the record among the 1758-1763 is carried out.
Embodiment 2: the insecticidal activity test
The halogen worm (brine shrimp) also claim the salt solution fairy shrimp, belongs to Arthropoda in the classification, Crustachia, Anostraca, salt solution fairy shrimp section, genus artemia.The halogen worm is as a kind of insecticide screening model; Relevant report has been arranged, [agricultural chemicals, 2011 such as Wang Zaiqiang both at home and abroad; 50 (4): 261-263] with the halogen worm as the model biological assessment insecticidal activity of 14 kinds of common insecticides; The result shows the compound that has insecticidal activity with the screening of halogen worm, and method is easy, and responsive to the insecticide of multiple different effects mechanism; Hu Zhiyu etc. [ocean circular, 2000,19 (4): 36-41] as indicator organism, have the compound of insecticidal activity with the halogen worm in the rapid screening marine actinomycete; [J.Antibiot, 1989,42 (8): 1304-1307] such as Blizzard T.A. are with the analog of halogen worm rapid screening insecticide AVM.In a word, the halogen worm has advantages such as wide material sources, amount simple to operate, required compound are few as the model biology of insecticidal activity assay, can improve screening effeciency greatly, and is significant to the research and development of new agricultural insecticide.
1) hatching of artemia cysts
Get artemia cysts 100mg and place the 500mL beaker, add artificial seawater 400mL, slowly inflate with inflator pump, room temperature hatching 24h removes chorion and unhatched ovum, and the halogen worm continues to cultivate 24h, and is subsequent use.
2) preparation of sample solution
Testing compound dissolves with DMSO, is formulated as 4mg/mL solution, and be diluted to according to this 2,1 with 0.5mg/mL solution, subsequent use.
3) test method
According to the Solis improved method, get 96 porocyte culture plates, every hole adds the artificial seawater liquid that 195 μ L contain 10-15 halogen worm, processes the test cultures plate.The blank group is respectively established three parallel holes with each concentration sample sets, and the blank group adds 5 μ L artificial seawaters, and sample sets adds the sample liquid of 5 μ L desired concns.After the incubated at room temperature 24 hours, under the binocular anatomical lens, detect the dead individual number of counting halogen worm.
The deadly activity of halogen worm representes that with corrected mortality computing formula is following:
Corrected mortality=(control group survival rate-processed group survival rate)/control group survival rate * 100%, and calculate half lethality rate LD
50Value.
Result of the test is the LD of compound tetradehydroechinulin (formula one) and didehydroechinulin (formula two)
50Value is respectively 19.8 and 27.1 μ g/mL, has better insecticidal activity.
Above-mentioned experimental result proof compound involved in the present invention has better insecticidal activity, and they can be used for preparing agricultural insecticide.
Claims (2)
1. the application of an indole dione piperazine derivative is characterized in that: the indole dione piperazine derivative can be used for preparing agricultural insecticide; Said indole dione piperazine derivative is shown in formula () or the formula (two);
Formula (one) formula (two).
2. the application of the described indole dione piperazine derivative of claim 1 is characterized in that: said insecticide formulation can be prepared into liquid, sustained release agent or powder.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201210151080 CN102669110B (en) | 2012-05-16 | 2012-05-16 | Application of indole diketopiperazine derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201210151080 CN102669110B (en) | 2012-05-16 | 2012-05-16 | Application of indole diketopiperazine derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102669110A true CN102669110A (en) | 2012-09-19 |
| CN102669110B CN102669110B (en) | 2013-06-19 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN 201210151080 Active CN102669110B (en) | 2012-05-16 | 2012-05-16 | Application of indole diketopiperazine derivatives |
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| CN (1) | CN102669110B (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104098549A (en) * | 2014-08-01 | 2014-10-15 | 华东理工大学 | Piperazinedione derivative and preparation and application thereof |
| CN104098549B (en) * | 2014-08-01 | 2017-01-04 | 华东理工大学 | Diketopiperazines and preparation thereof and purposes |
| CN111235036A (en) * | 2020-01-15 | 2020-06-05 | 西北大学 | Eurotium cristatum and method for separating and purifying diketopiperazine dimer from eurotium cristatum |
| CN112237582A (en) * | 2020-01-15 | 2021-01-19 | 西北大学 | Use of diketopiperazine dimers |
| WO2022113987A1 (en) * | 2020-11-30 | 2022-06-02 | 学校法人東京理科大学 | Novel compound, antiviral agent for positive-strand rna, and inhibitor of lipid droplet formation |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005063740A1 (en) * | 2003-12-31 | 2005-07-14 | Council Of Scientific And Industrial Research | Chrysogenazine obtained from fungus penicillium chrysogenum having antibacterial activity |
-
2012
- 2012-05-16 CN CN 201210151080 patent/CN102669110B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005063740A1 (en) * | 2003-12-31 | 2005-07-14 | Council Of Scientific And Industrial Research | Chrysogenazine obtained from fungus penicillium chrysogenum having antibacterial activity |
Non-Patent Citations (2)
| Title |
|---|
| HUI-JIAO YAN ET AL.: "Alkaloid and Anthraquinone Derivatives Produced by the Marine-Derived Endophytic Fungus Eurotium rubrum", 《HELVETICA CHIMICA ACTA》 * |
| LI-NA ZHOU ET AL: "Three New Indole-Containing Diketopiperazine Alkaloids from a Deep-Ocean Sediment Derived Fungus Penicillium griseofulvum", 《HELVETICA CHIMICA ACTA》 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104098549A (en) * | 2014-08-01 | 2014-10-15 | 华东理工大学 | Piperazinedione derivative and preparation and application thereof |
| CN104098549B (en) * | 2014-08-01 | 2017-01-04 | 华东理工大学 | Diketopiperazines and preparation thereof and purposes |
| CN111235036A (en) * | 2020-01-15 | 2020-06-05 | 西北大学 | Eurotium cristatum and method for separating and purifying diketopiperazine dimer from eurotium cristatum |
| CN112237582A (en) * | 2020-01-15 | 2021-01-19 | 西北大学 | Use of diketopiperazine dimers |
| CN111235036B (en) * | 2020-01-15 | 2022-03-18 | 西北大学 | Eurotium cristatum and method for separating and purifying diketopiperazine dimer from eurotium cristatum |
| WO2022113987A1 (en) * | 2020-11-30 | 2022-06-02 | 学校法人東京理科大学 | Novel compound, antiviral agent for positive-strand rna, and inhibitor of lipid droplet formation |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102669110B (en) | 2013-06-19 |
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