CN102669110B - Application of indole diketopiperazine derivatives - Google Patents
Application of indole diketopiperazine derivatives Download PDFInfo
- Publication number
- CN102669110B CN102669110B CN 201210151080 CN201210151080A CN102669110B CN 102669110 B CN102669110 B CN 102669110B CN 201210151080 CN201210151080 CN 201210151080 CN 201210151080 A CN201210151080 A CN 201210151080A CN 102669110 B CN102669110 B CN 102669110B
- Authority
- CN
- China
- Prior art keywords
- formula
- application
- diketopiperazine derivatives
- analog derivative
- diketopiperazine compounds
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
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, specifically a kind of application of Indolyl diketopiperazine compounds analog derivative.
Background technology
Estimate according to the FAO of the World Food Programme, the grain loss that causes of annual due to illness insect pest approximately 20% in the world, cotton loss approximately 30%, the loss of fruit tree, vegetables approximately 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 mostly lower to mammalian toxicity, and is safer to people and animals in 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 Indolyl diketopiperazine compounds analog derivative.
For achieving the above object, the technical solution adopted in the present invention is:
A kind of application of Indolyl diketopiperazine compounds analog derivative, the Indolyl diketopiperazine compounds analog derivative can be used for preparing agricultural insecticide; Described Indolyl diketopiperazine compounds analog derivative is shown in formula () or formula (two);
Described insecticide formulation can be prepared into liquid, sustained release agent or powder.
The present invention has advantages of:
1) Indolyl diketopiperazine compounds compounds involved in the present invention is separated and obtains through fermented and cultured, extraction by the loose capsule bacterium (Eurotium cristatum) of coronoid process, and have the lethal activity of better halogen worm, a compound tetradehydroechinulin(formula one) and didehydroechinulin(formula two) to the LD of halogen worm
50Value is respectively 19.8 and 27.1 μ g/mL.
2) Indolyl diketopiperazine compounds analog derivative involved in the present invention can be used as novel pesticide composition or the lead compound with insecticidal action.
The characteristics such as 3) Indolyl diketopiperazine compounds analog derivative involved in the present invention can utilize microorganism to carry out the scale fermentation, has production technology simple, and the cycle is short, product cost is low.
Embodiment
For illustrating the understanding to feature of the present invention, below in conjunction with some non-limiting embodiments, the present invention is further elaborated.
Embodiment 1:
The Indolyl diketopiperazine compounds analog derivative is the Indolyl diketopiperazine compounds analog derivative shown in formula () or formula (two), the compound of its formula () and formula (two) is respectively tetradehydroechinulin and didehydroechinulin, is Indolyl diketopiperazine compounds class known compound.
Wherein, Indolyl diketopiperazine compounds class known compound tetradehydroechinulin(formula one) and didehydroechinulin(formula two) preparation process can be respectively referring to document Helv.Chim.Acta, 2012,95,163 – 168 and Helv.Chim.Acta, record in 2010,93,1758 – 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 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 both at home and abroad, the king waits by force [agricultural chemicals again, 2011,50 (4): 261 – 263] with the halogen worm as the model biological assessment insecticidal activity of 14 kinds of common insecticides, 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 mechanism of action; 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 Avermectin.In a word, the halogen worm has the advantages such as wide material sources, amount simple to operate, required compound are few as the model biology of insecticidal activity assay, can greatly improve screening effeciency, and is significant to the research and development of new agricultural insecticide.
1) hatching of halogen worm's ovum
Get halogen worm's ovum 100mg and be placed in 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 standby.
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, standby.
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, makes the test cultures plate.Blank group and each concentration sample sets are respectively established three parallel holes, and the blank group adds 5 μ L artificial seawaters, and sample sets adds the sample liquid of 5 μ L desired concns.After incubated at room temperature 24 hours, detect the dead individual amount of counting halogen worm under the binocular anatomical lens.
The lethal activity of halogen worm represents with corrected mortality, and computing formula is as follows:
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 compound tetradehydroechinulin(formula one) and didehydroechinulin(formula two) LD
50Value is respectively 19.8 and 27.1 μ g/mL, has better insecticidal activity.
Above-mentioned the results show 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 Indolyl diketopiperazine compounds analog derivative is characterized in that: the Indolyl diketopiperazine compounds analog derivative can be used for preparing agricultural insecticide; Described Indolyl diketopiperazine compounds analog derivative is shown in formula () or formula (two);
Formula (one) formula (two).
2. the application of Indolyl diketopiperazine compounds analog derivative claimed in claim 1 is characterized in that: described 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 CN102669110A (en) | 2012-09-19 |
| CN102669110B true CN102669110B (en) | 2013-06-19 |
Family
ID=46802204
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 201210151080 Active CN102669110B (en) | 2012-05-16 | 2012-05-16 | Application of indole diketopiperazine derivatives |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102669110B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| JPWO2022113987A1 (en) * | 2020-11-30 | 2022-06-02 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1709031A1 (en) * | 2003-12-31 | 2006-10-11 | 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
Also Published As
| Publication number | Publication date |
|---|---|
| CN102669110A (en) | 2012-09-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102308852B (en) | Microorganism algae-inhibiting agent capable of inhibiting free microalgae or membrane microalgae in water and preparation method thereof | |
| CN103749441B (en) | Isaria fumosorosea wettable powder as well as preparation method and application thereof | |
| CN102187870B (en) | Application of diterpene alkaloid compound serving as secondary metabolite of seaweed endophytic fungus | |
| CN105410032B (en) | A kind of microorganism trapping bait and application | |
| CN102337219B (en) | Saccharopolyspora spinosa strain, application of saccharopolyspora spinosa strain and method for preparing spinosad | |
| CN102342299A (en) | Empedobacter brevis pesticide and preparation method thereof | |
| Grahovac et al. | Bacillus VOCs in the context of biological control | |
| CN102669110B (en) | Application of indole diketopiperazine derivatives | |
| KR101877932B1 (en) | Composition for controlling nematode comprising grammicin compound as effective component and uses thereof | |
| CN103749545B (en) | Rose dark brown Isaria and bacillus thuringiensis,Bt wetting powder | |
| CN102676393B (en) | Saccharopolyspora spinosa for producing spinosad and culture and application of saccharopolyspora spinosa | |
| CN104593281A (en) | A plurality of indolocarbazole alkaloids having strong insect disinfestation activities, and production strain thereof | |
| CN102177893B (en) | Bactericide | |
| CN103484393A (en) | Klebsiella inoculum capable of biodegrading residual chlorpyrifos pesticide on surfaces of garden stuffs and soil | |
| CN103045488B (en) | Beauveria felina AS-70 strain and application thereof | |
| CN102273456B (en) | Application of beta-dihydro benzoic acid macrolide derivant in preventing and treating harmful spiral shells | |
| CN102659547B (en) | Ophiobolin sesterterpene compound and preparation and application thereof | |
| CN102675293B (en) | Indole diketopiperazines derivatives, preparation method and application thereof | |
| CN101538605B (en) | Method for screening degradation bacteria strains by taking high-efficiency cyhalothrin as substrate | |
| CN108184906A (en) | A kind of preparation method of attractive insecticide for fruit fly | |
| CN107200790A (en) | A kind of chitosan oligosaccharide derivative and its preparation method and application | |
| CN102701935B (en) | Tetranuclear diterpenoids as well as preparation and application thereof | |
| Mathivanan et al. | Utilization of Shrimp waste as a novel media for marine bacteria isolation | |
| CN109699683A (en) | A kind of talcum matrix Java cordyceps sinensis spore preparation | |
| CN103333831A (en) | Method for outdoor domestication and purification of empedobacter brevis GXW15-4 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant |