CN108552175A - The application of oleanolic acid and its derivative in preventing planthopper - Google Patents
The application of oleanolic acid and its derivative in preventing planthopper Download PDFInfo
- Publication number
- CN108552175A CN108552175A CN201810434199.7A CN201810434199A CN108552175A CN 108552175 A CN108552175 A CN 108552175A CN 201810434199 A CN201810434199 A CN 201810434199A CN 108552175 A CN108552175 A CN 108552175A
- Authority
- CN
- China
- Prior art keywords
- olive
- alkene
- oleanolic acid
- methyl
- methyl esters
- 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.)
- Pending
Links
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/34—Nitriles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing within the same carbon skeleton a carboxylic group or a thio analogue, or a derivative thereof, and a carbon atom having only two bonds to hetero atoms with at the most one bond to halogen, e.g. keto-carboxylic acids
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/12—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings condensed with a carbocyclic ring
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
- A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The present invention relates to field of natural medicinal chemistry and biological pesticide technical field, application of any compound in preventing brown paddy plant hopper in a kind of oleanolic acid and its derivative is disclosed.Since oleanolic acid raw material sources of the present invention are easy to get, and have the characteristic of botanical pesticide, have the characteristics that nuisanceless, safe and efficient, can develop suitable for the botanical pesticide for production green, pollution-free agricultural product, to belong to novel biopesticide.
Description
Technical field
The invention belongs to technical field of pesticide, disclose a kind of new application of oleanolic acid and its derivative, and in particular to
The application of oleanolic acid and its derivative as biological pesticide in preventing planthopper.
Background technology
Planthopper is the pest of the most of Rice Production state facings in Asia, has remote habit of migrating, because of breeding
Multiple is high, is endangered in rice base portion piercing and sucking, easily population outbreak.Planthopper occurring area remains high always, and prevention pressure is bright
It is aobvious to rise.According to statistics, 2011-2013 occurring areas ratio 2001-2010 increases by 14.5%, than 1991-2000, increases
68.4%；Area is prevented up to 600,000,000 mu times, increases by 13.2% than 2001-2010, increases nearly 1 times than 1991-2000.Currently
Imidacloprid, chlopyrifos, cartap, Buprofezin, pymetrozine etc. are due to repeatedly using year after year, " 3R " problem of current planthopper
Seriously, drug resistance rises.The optional high-efficiency low-toxicity medicament for being adapted to prevention rice hoppers is fewer, thus finds efficient
Low planthopper medicament has become one of the major subjects of current plant protection scientific worker.Botanical pesticide is because generally acknowledging it with low
The advantages that poison, noresidue, high selectivity, easy decomposition, pest are not likely to produce drug resistance, and receive researcher's pro-gaze.It is provided from plant
Potential desinsection lead compound is found and screened in source, and carries out the important way that structure optimization has become novel pesticide initiative
One of diameter and research hotspot.
Natural source pentacyclic triterpenoid is distributed in various plants, has extensive bioactivity, while also to more
Kind agricultural pests show preferable control effect.(①Phytochem Rev(2011)10:245–260；②
Ecotoxicology and Environmental Safety 72(2009)1156–1162；③Chemosphere 67
(2007)80–88；④Pesticide Biochemistry and Physiology 81(2005)113–122).Oleanolic acid
(Oleanic acid) belongs to pentacyclic triterpene compound, is widely distributed in various plants in the form of free or be combined into glycosides,
In the plants such as leaf, the gentianaceae plant swertia mileensis herb of main extraction source Oleaceae plants olive.It is with AntiHIV1 RT activity, anti-
The multiple biological activities such as bacterium, anticancer, antiulcer, treatment osteoporosis, because its activity is various, content is higher in plant, at
The natural source guide structure modified and optimized extensively for current Pharmaceutical Chemist.
Invention content
Purpose of the present invention is in view of the defects existing in the prior art, a kind of natural plant desinsection be provided for agricultural production
The application of the new application of agent --- -- oleanolic acid and its derivative, i.e. oleanolic acid as pesticide in preventing brown paddy plant hopper.
To achieve the above object, the present invention provides following technical solutions：
The application of oleanolic acid and its derivative in preventing planthopper.
Above-described oleanolic acid and its derivative include：Oleanolic acid, 3- acetyl group oleanolic acid, 3- hydroxyls -28-
Methyl esters oleanolic acid, 3 beta-hydroxy-N- morpholines-olive -12- alkene -28- amides, 3 beta-hydroxy-N- pyrrolidines-olive -12-
Alkene -28- amides, 3 beta-hydroxy-N- piperidines-olive -12- alkene -28- amides, 3 beta-hydroxy-N- (2- pyridines)-olive -12-
Alkene -28- amides, 3 beta-hydroxy-N- hydroxyls-olive -12- alkene -28- amides, 3- ketone oleanolic acid, 3- ketone -2- bromine olives
Acid, 3- oximes oleanolic acid, 3- amino oleanolic acid, the bromo- olive -28- formic acid -28,13- lactones of 3- ketone -12-, olive -2-
Alkene [2,3-b] pyrazine -28- formic acid, indoles [3,2-b] olive -12- alkene -28- formic acid, 3- ketone -28- methyl esters oleanolic acid, first
Base -3- ketone -2- benzylidenes-olive -12- alkene -28- methyl esters, methyl -3- ketone -2- (4- fluorobenzylidenes)-olive -12-
Alkene -28- methyl esters, methyl -2,3- (5- phenyl) -4,5- dihydro-1 h-pyrazoles base-olive -12- alkene -28- methyl esters, methyl-are different
Oxazole [4,5-b] olive -12- alkene -28- methyl esters, methyl-2-amino pyrimidine [3,2-b] olive -12- alkene -28- methyl esters, first
Base -2- cyano -4- subunits-olive -12- alkene -28- methyl esters, -18 β-H- olive -28- methyl esters of methyl -3,12- diketone.Before
It states oleanolic acid and its derivative and is referred to as compound 1- compounds 23 successively in sequence.
It is a kind of that pesticidal preparations that preventing planthopper are being prepared by the oleanolic acid and its derivative of any description above, including
Oleanolic acid of any description above or derivatives thereof, and oleanolic acid or derivatives thereof and auxiliary material pesticide-acceptable are mixed
Pesticidal preparations are prepared in conjunction.
As being further improved for technical solution, above-described pesticidal preparations, described oleanolic acid or derivatives thereof has
The weight percentage that effect ingredient accounts for the pesticidal preparations is 1%-99%.
As being further improved for technical solution, the dosage form of above-described pesticidal preparations, the pesticidal preparations is micro-capsule
One kind in suspending agent, suspending agent, water dispersible granules, dry suspending agent, wettable powder, missible oil, aqueous emulsion or granule.
Above-described pesticidal preparations are in the application in preventing planthopper.
Further, oleanolic acid derivate preparation method of the present invention is obtained according to the synthetic method of the report of document
The compound obtained.It is detached through conventional methods such as multiple silica gel column chromatographies and obtains sterling, through the spectroscopic techniques such as mass spectrum and nuclear magnetic resonance,
Claim oleanolic acid and its derivative, i.e. compound 1- compounds 23 is determined, structural formula is as shown in attached drawing 1-23.Through
Active ingredients result shows that oleanolic acid derivate of the present invention shows stronger inhibiting effect to brown paddy plant hopper, can use
In preparing insecticide.
Natural source pentacyclic triterpenoid have it is efficient, less toxic, pollution-free, to safety of human and livestock, the mode of action uniqueness, select
Selecting property is high, the natural products of drug resistance etc. is not likely to produce to natural enemy and beneficial organism safety and pest pathogen, meets people couple
The requirement of ideal pesticide, but only a small number of plant terpene compounds are used widely in plant protection at present.Oleanolic acid
Belong to biological pesticide as a kind of natural source alkaloid, compared with chemical pesticide, advantage of the present invention is：
1) insecticidal activity is high, can be used as new prevention planthopper guide and carries out biorational exploitation.
2) compound provided by the invention has excellent lethal effect to planthopper, to be provided in agricultural insect pest's prevention
A kind of natural source insecticide active substance；As fungicide, efficiently, low toxicity, it is safe the features such as meet current novel pesticide wound
The requirement of system.
Description of the drawings
Fig. 1 is the oleanolic acid structural schematic diagram of the present invention.
Fig. 2 is the 3- acetyl group oleanolic acid structural schematic diagrams of the present invention.
Fig. 3 is the 3- hydroxyl -28- methyl esters oleanolic acid structural schematic diagrams of the present invention.
Fig. 4 is 3 beta-hydroxy-N- morpholines-olive -12- alkene -28- amide structure schematic diagrames of the present invention.
Fig. 5 is 3 beta-hydroxy-N- pyrrolidines-olive -12- alkene -28- amide structure schematic diagrames of the present invention.
Fig. 6 is 3 beta-hydroxy-N- piperidines-olive -12- alkene -28- amide structure schematic diagrames of the present invention.
Fig. 7 is 3 beta-hydroxy-N- (2- pyridines)-olive -12- alkene -28- amide structure schematic diagrames of the present invention.
Fig. 8 is 3 beta-hydroxy-N- hydroxyls-olive -12- alkene -28- amide structure schematic diagrames of the present invention.
Fig. 9 is the 3- ketone oleanolic acid structural schematic diagrams of the present invention.
Figure 10 is the 3- ketone -2- bromine oleanolic acid structural schematic diagrams of the present invention.
Figure 11 is the 3- oxime oleanolic acid structural schematic diagrams of the present invention.
Figure 12 is the 3- amino oleanolic acid structural schematic diagrams of the present invention.
Figure 13 is the bromo- olive -28- formic acid -28,13- lactone structure schematic diagrames of 3- ketone -12- of the present invention.
Figure 14 is olive -2- alkene [2,3-b] pyrazine -28- formic acid structural schematic diagrams of the present invention.
Figure 15 is indoles [3,2-b] olive -12- alkene -28- formic acid structural schematic diagrams of the present invention.
Figure 16 is the 3- ketone -28- methyl esters oleanolic acid structural schematic diagrams of the present invention.
Figure 17 is methyl -3- ketone -2- benzylidenes-olive -12- alkene -28- methyl esters structural schematic diagrams of the present invention.
Figure 18 is methyl -3- ketone -2- (4- fluorobenzylidenes)-olive -12- alkene -28- methyl esters structural representations of the present invention
Figure.
Figure 19 is methyl -2,3- (5- phenyl) -4,5- dihydro-1 h-pyrazoles base-olive -12- alkene -28- first of the present invention
Ester structure schematic diagram.
Figure 20 is methyl-isoxazole [4,5-b] olive -12- alkene -28- methyl esters structural schematic diagrams of the present invention.
Figure 21 is methyl-2-amino pyrimidine [3,2-b] olive -12- alkene -28- methyl esters structural schematic diagrams of the present invention.
Figure 22 is methyl -2- cyano -4- subunits-olive -12- alkene -28- methyl esters structural schematic diagrams of the present invention.
Figure 23 is -18 β-H- olive -28- methyl esters structural schematic diagrams of methyl -3,12- diketone of the present invention.
Specific implementation mode
For a better understanding of the present invention, below by way of specific implementation mode, the above of the present invention is done further
Detailed description.But this should not be interpreted as limitation of the present invention.Experimental method described in following embodiments, such as without special theory
It is bright, it is conventional method.
The preparation of oleanolic acid and its derivative
Compound 1 (oleanolic acid) commercial sources are commercially available.
Compound 2 (reference literature Journal of Medicinal Chemistry 2009,52,3248-3258)
Compound 4,5,6,7,8 (reference literature European Journal of Medicinal Chemistry 2014,
87,159-167)
Compound 9,14,15 (reference literature European Journal of Medicinal Chemistry 2009,
44,2796-2806)
Compound 11 (reference literature Journal of Agricultural and Food Chemistry 2006,54,
3566-3571)
(the reference literature Bioorganic＆Medicinal Chemistry Letters 2009,19,6618- of compound 21
6622)
(the reference literature European Journal of Medicinal of compound 3,16,17,18,19,20
Chemistry 2014,74,398-404)
(the reference literature Bioorganic＆Medicinal Chemistry Letters 2004,14,4723- of compound 22
4726；Journal of Organic Chemistry 2003,68,4833-4844)
(the reference literature European Journal of Medicinal Chemistry 2015,92,700- of compound 10
711)
(the reference literature European Journal of Medicinal Chemistry 2014,72,84- of compound 13
101)
(the reference literature European Journal of Medicinal Chemistry 2015,95,240- of compound 12
248)
Compound 23 (reference literature Journal of Natural Products, 2010,73,1743-1750)
It is obtained with reference to the synthetic method for having document report, through physical property and nucleus n-ness spectrum identification and document report
It is consistent, it is determined that the oleanolic acid cited by claim and its derivative, i.e. compound 1- compounds 23, structural formula is such as
Shown in attached drawing 1-23.All compounds detach through conventional methods such as multiple silica gel column chromatographies and obtain sterling, for further activity
Test.
Oleanolic acid and its derivative are to brown paddy plant hopper killing activity measurement and result
1) oleanolic acid and its derivative of chemical formula 1-23.
2) for trying insect：Brown paddy plant hopper.
3) bioassay method：Activity of the oleanolic acid derivate to brown paddy plant hopper (3 age) is measured using leaching rice straw method, it will
5mg compounds are dissolved into respectively in 5mL (MeOH/NMP/NP-10) mixed solution, are configured to the medicine that mass concentration is 1000mg/L
Liquid, take its 1mL again with acetone be diluted to respectively 25,50,100,200 and 500mg/L for reagent liquid.Respectively take 20mL for reagent liquid
It is placed in teat glass, takes healthy rice straw to impregnate 15-20s, compared with blank solvent.Each a concentration of processing, is often handled
It is repeated 2 times.Teat glass is placed in 25 DEG C of insulating boxs after processing, 48h, 72h check the survival of brown paddy plant hopper and dead after processing
Die number.
1 oleanolic acid of table and its derivative act on 48 hours killing activity test results to brown paddy plant hopper
2 oleanolic acid of table and its derivative act on 72 hours killing activity test results to brown paddy plant hopper
It is given birth to by upper table and surveys result it is found that oleanolic acid derivate prepared by the present invention shows preferably to inhibit to brown paddy plant hopper
Activity, which part compound at 100ppm to brown paddy plant hopper inhibitory activity up to 60% or more, or even show better activity,
Thus compound of the present invention can be used for preparing the purposes in pesticide.In conclusion oleanolic acid of the present invention its
It derives from a wealth of sources, is easy to derivative synthesis, and some compounds show significant inhibitory activity to brown paddy plant hopper, there is further research
Value, be expected to be developed into novel botanical pesticide.
The preparation embodiment 1 of pesticidal preparations：20% oleanolic acid microcapsule suspending agent
Formula composition：20% oleanolic acid active compound, 0.5% polyisocyanates, 0.8% oil based polyether polyol, 0.2%
Triethylenediamine, 0.02% dibutyltin dilaurate, 0.4% methyl diphenylene diisocyanate, 6% alkyl benzene sulphonate
Salt, 1% polyoxypropylene hexadecyl ethylene oxide addition product, 0.2% xanthans, 4% glycerine, 0.3% sodium benzoate, 0.1% is organic
Silicon, water supply 100%.
It is spare by each component has been weighed with above-mentioned formula composition, 1. by oleanolic acid, oil based polyether polyol, triethylene
Base diamines, dibutyltin dilaurate, methyl diphenylene diisocyanate are uniformly mixed, and after stirring 8~10s, polyisocyanate is added
Cyanate, then be stirred to starting adstante febre and stop, stand foaming and curing, foamed time are 5min~for 24 hours, and foaming is complete
Afterwards 10 microns of semi-finished product fine particles below are crushed to pulverizer.
2. 1. the semi-finished product fine particle of gained, alkylbenzene sulfonate, polyoxypropylene hexadecyl ethylene oxide are added in water to add
At object, xanthans, glycerine, sodium benzoate, organosilicon are stirred into microcapsule suspending agent.
Oleanolic acid can be replaced into 3 beta-hydroxy-N- piperidines-olive -12- alkene -28- amides, 3 beta-hydroxy-N- respectively
(2- pyridines)-olive -12- alkene -28- amides form the preparation embodiment of new pesticidal preparations.
The preparation embodiment 2 of pesticidal preparations：10%3- acetyl group oleanolic acid suspending agents
Formula composition：10%3- acetyl group oleanolic acid, 3% di-2-ethylhexylphosphine oxide methyl naphthalene sulfonic acid (wetting dispersing agent), 2% the third
Olefin(e) acid (is carried with propionamide copolymer (wetting dispersing agent), 0.5% ethylene glycol (antifreezing agent), 0.2% xanthans (thickener), water
Body) supply 100%.
It is spare to have weighed each component by above-mentioned formula composition, then by di-2-ethylhexylphosphine oxide methyl naphthalene sulfonic acid (wetting dispersing agent),
Acrylic acid and propionamide copolymer (wetting dispersing agent), ethylene glycol (antifreezing agent), xanthans (thickener), water (carrier) are tentatively mixed
It closes, then moves into high speed shear kettle high speed cutting kettle and be uniformly mixed, be eventually adding 10%3- acetyl group oleanolic acids in abrading-ball
10%3- acetyl group oleanolic acid suspending agents are made in abrading-ball 2~3 hours in machine.
The preparation embodiment 3 of pesticidal preparations：40%3- hydroxyl -28- methyl esters oleanolic acid water dispersible granules
Formula composition：40%3 beta-hydroxy-N- morpholines-olive -12- alkene -28- amides %, 3% lauryl sodium sulfate,
4% di-2-ethylhexylphosphine oxide bitter edible plant sodium sulfonate (abbreviation NNO), 5% white carbon, 2% ammonium sulfate, kaolin supply 100%.
It is spare that each component has been weighed by above-mentioned formula composition, and then each component is uniformly mixed, is crushed through airslide disintegrating mill
Afterwards, 30min is stirred, through mediating, rear be added in fluidized-bed granulation dryer is granulated, dries, obtain 40%3- hydroxyls -28-
Methyl esters oleanolic acid water dispersible granules.
3- hydroxyl -28- methyl esters oleanolic acids can be substituted for methyl-2-amino pyrimidine [3,2-b] olive-respectively
12- alkene -28- methyl esters, methyl -2- cyano -4- subunits-olive -12- alkene -28- methyl esters form new embodiment.
The preparation embodiment 4 of pesticidal preparations：50%3 beta-hydroxy-N- morpholines-olive -12- alkene -28- amide wettable powders
Agent
Formula composition：50%3 beta-hydroxy-N- morpholines-olive -12- alkene -28- amides, 5.2% lauryl sodium sulfate,
3.8% acrylic acid and propionamide copolymer, 6% white carbon, diatomite supply 100%.
It is spare that each component has been weighed by above-mentioned formula composition, then each combination has been mixed, then through airslide disintegrating mill powder
After broken, 30min is stirred, 50%3 beta-hydroxy-N- morpholines-olive -12- alkene -28- amide wettable powders are obtained.
3 beta-hydroxy-N- morpholines-olive -12- alkene -28- amides can be substituted for 3- ketone oleanolic acid, 3- ketone-respectively
2- bromines oleanolic acid, 3- oximes oleanolic acid, 3- amino oleanolic acids form new embodiment.
The preparation embodiment 5 of pesticidal preparations：60%3 beta-hydroxy-N- pyrrolidines-olive -12- alkene -28- amides are dry to suspend
Agent
Formula composition：60%3 beta-hydroxy-N- pyrrolidines-olive -12- alkene -28- amides, 15% sodium lignin sulfonate,
10% naphthalenesulfonate formaldehyde condensation compound, 0.2% antifoaming agent, sodium sulphate supply 100%.
Each component raw material has been weighed respectively by above-mentioned formula composition in blending tank, is started and is uniformly mixed to obtain active compound
Mixture is put into homogenizer, according to active compound mixture quality than 1:1 is pumped into deionized water, starts cutter, evenly dispersed original
Medicine mixture obtains 30% beta-hydroxy-N- pyrrolidines-olive -12- alkene -28- amide coarse particles；It is pumped into sand mill grinding again
Certain time makes material particular diameter≤5 μm, suspends to obtain 30% beta-hydroxy-N- pyrrolidines-olive -12- alkene -28- amides
Slurry；Suspended nitride is finally subjected to pressure spray dryer or atomizer is dried, 50% moisture is evaporated, is made 60%3
Beta-hydroxy-N- pyrrolidines-olive -12- alkene -28- amide dry suspending agents.
3 beta-hydroxy-N- pyrrolidines-olive -12- alkene -28- amides can be substituted for the neat pier of 3- ketone -28- methyl esters respectively
Tartaric acid, methyl -3- ketone -2- benzylidenes-olive -12- alkene -28- methyl esters, methyl -3- ketone -2- (4- fluorobenzylidenes)-are neat
Pier fruit -12- alkene -28- methyl esters, methyl-isoxazole [4,5-b] olive -12- alkene -28- methyl esters form new embodiment.
The preparation embodiment 6 of pesticidal preparations：Emulsifiable concentrate in the bromo- olive -28- formic acid -28,13- of 30%3- ketone -12-
Formula composition：Bromo- olive -28- formic acid -28, the 13- lactones of 30%3- ketone -12-, 5% nonylphenol polyoxyethylene ether
(emulsifier), 3% alkylaryl polyoxyethylene polyoxypropylene ether again, methyl oleate supply 100%.
Each component raw material has been weighed respectively by above-mentioned formula composition, and each component raw material, which is then put into mixing in mixing kettle, stirs
It mixes, transparency liquid is obtained after stirring evenly, obtains emulsifiable concentrate in the bromo- olive -28- formic acid -28,13- of 30%3- ketone -12-.
Bromo- olive -28- formic acid -28,13- the lactones of 3- ketone -12- can be respectively substituted for olive -2- alkene [2,3-
B] pyrazine -28- formic acid, indoles [3,2-b] olive -12- alkene -28- formic acid forms new embodiment.……….
The preparation embodiment 7 of pesticidal preparations：- 18 β-H- olive -28- methyl esters aqueous emulsions of 6% methyl -3,12- diketone
Formula composition：- 18 β-H- olive -28- methyl esters of 6% methyl -3,12- diketone, 10%N- methyl pyrrolidones are (molten
Agent), 5% nonylphenol polyoxyethylene ether (emulsifier), 3% alkylaryl polyoxyethylene polyoxypropylene ether again (emulsifier), 1% nonyl
Phenol polyethenoxy ether (emulsifier), 3% ethylene glycol (antifreezing agent), 0.2% organosilicon (antifoaming agent) water supply 100%.
- 18 β-H- olive -28- methyl esters of methyl -3,12- diketone will be dissolved with solvent, and it is mixed then to sequentially add emulsifier
It closes, is dissolved into uniform oil phase；Part water, antifreezing agent, antifoaming agent are mixed into uniform water phase；It is high in a kettle
The oil phase is added to the aqueous phase while speed stirring, opens cutter and carries out high speed shear, and is supplied by adding the remaining water, shearing about half
Hour, aqueous emulsion is formed, -18 β-H- olive -28- methyl esters aqueous emulsions of 6% methyl -3,12- diketone are obtained.
The preparation embodiment 8 of pesticidal preparations：0.5% methyl -2,3- (5- phenyl) -4,5- dihydro-1 h-pyrazoles Ji-neat pier
Fruit -12- alkene -28- methacrylate particles agent
Formula composition：0.5% methyl -2,3- (5- phenyl) -4,5- dihydro-1 h-pyrazoles base-olive -12- alkene -28- first
Ester, 2.6% sodium lignin sulfonate (wetting dispersing agent), 3.4% poly carboxylic acid derivative (wetting dispersing agent), 2% starch, 1% sulphur
Sour ammonium, urea (filler) 10%, bentonite (filler) supply 100%
Each component raw material has been weighed respectively by above-mentioned formula composition, has then been uniformly mixed each component raw material, has been crushed,
It stirs, then is granulated with screw extruder pelletizer after wetting with water, is sieved after dry to get 0.5% methyl -2,3-
(5- phenyl) -4,5- dihydro-1 h-pyrazoles base-olive -12- alkene -28- methacrylate particles agent
Pesticidal preparations apply field trial
Test method：Reference《GB/T 17980.4-2000 pesticide field efficacy medicine test criterions (one) insecticide control rice
Plant hopper》.Controlling object：Planthopper；Application method：Conventional spraying.
Comparison medicament 1：25% Diacloden wettable powder (registration card number PD20172724, producer：Guangxi rural area biochemistry stock
Part Co., Ltd)
Comparison medicament 2：20% clothianidin suspending agent (registration card number PD20181268, producer：Liuzhou City's Huinong's chemical industry is limited
Company)
Further also active ingredient weight percentage is prepared in other oleanolic acids or derivatives thereof by applicant
Suspending agent, suspension emulsion, missible oil, aqueous emulsion, microemulsion, dispersible oil-suspending agent or the water dispersible granules of 1%-99%, then into
Row field trial substantially can reach the field test effect of aforementioned table record.
Claims (6)
1. the application of oleanolic acid and its derivative in preventing planthopper.
2. the application of oleanolic acid according to claim 1 and its derivative in preventing planthopper, it is characterised in that：Institute
The oleanolic acid and its derivative stated include：Oleanolic acid, 3- acetyl group oleanolic acid, 3- hydroxyl -28- methyl esters oleanolic acid, 3
Beta-hydroxy-N- morpholines-olive -12- alkene -28- amides, 3 beta-hydroxy-N- pyrrolidines-olive -12- alkene -28- amides, 3 β -
Hydroxy-n-piperidines-olive -12- alkene -28- amides, 3 beta-hydroxy-N- (2- pyridines)-olive -12- alkene -28- amides, 3 β -
Hydroxy-n-hydroxyl-olive -12- alkene -28- amides, 3- ketone oleanolic acid, 3- ketone -2- bromines oleanolic acid, 3- oximes oleanolic acid,
Bromo- olive -28- formic acid -28,13- the lactones of 3- amino oleanolic acid, 3- ketone -12-, olive -2- alkene [2,3-b] pyrazine -
28- formic acid, indoles [3,2-b] olive -12- alkene -28- formic acid, 3- ketone -28- methyl esters oleanolic acid, methyl -3- ketone -2- benzene are sub-
Methyl-olive -12- alkene -28- methyl esters, methyl -3- ketone -2- (4- fluorobenzylidenes)-olive -12- alkene -28- methyl esters, first
Base -2,3- (5- phenyl) -4,5- dihydro-1 h-pyrazoles base-olive -12- alkene -28- methyl esters, methyl-isoxazole [4,5-b] are neat
Pier fruit -12- alkene -28- methyl esters, methyl-2-amino pyrimidine [3,2-b] olive -12- alkene -28- methyl esters, methyl -2- cyano -4-
Subunit-olive -12- alkene -28- methyl esters, -18 β-H- olive -28- methyl esters of methyl -3,12- diketone.
3. a kind of require the 1-2 any oleanolic acid and its derivative preparing the pesticidal preparations for preventing planthopper by profit,
It is characterized in that：Including any oleanolic acids or derivatives thereof of claim 1-2, and by oleanolic acid or derivatives thereof
It is mixed with to obtain pesticidal preparations with auxiliary material pesticide-acceptable.
4. pesticidal preparations according to claim 3, it is characterised in that：The oleanolic acid or derivatives thereof active ingredient accounts for
The weight percentage of the pesticidal preparations is 1%-99%.
5. pesticidal preparations according to claim 5 or 6, it is characterised in that：The dosage form of the pesticidal preparations is microcapsule suspension
One kind in agent, suspending agent, water dispersible granules, dry suspending agent, wettable powder, missible oil, aqueous emulsion or granule.
6. the pesticidal preparations as described in claim 3-5 are in the application in preventing planthopper.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810434199.7A CN108552175A (en) | 2018-05-08 | 2018-05-08 | The application of oleanolic acid and its derivative in preventing planthopper |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810434199.7A CN108552175A (en) | 2018-05-08 | 2018-05-08 | The application of oleanolic acid and its derivative in preventing planthopper |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN108552175A true CN108552175A (en) | 2018-09-21 |
Family
ID=63538388
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810434199.7A Pending CN108552175A (en) | 2018-05-08 | 2018-05-08 | The application of oleanolic acid and its derivative in preventing planthopper |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN108552175A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112021339A (en) * | 2019-06-03 | 2020-12-04 | 南京臻旸生物科技有限公司 | Method for preparing biological pesticide and biological fertilizer from eucalyptus leaves and eucalyptus bark and product |
| CN112142818A (en) * | 2019-06-27 | 2020-12-29 | 中国药科大学 | Oleanolic acid and oleanolic acid derivatives and medical application thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104186470A (en) * | 2014-08-12 | 2014-12-10 | 南京金梧桐医药科技有限公司 | Application of ursolic acid to preparation of insecticide |
-
2018
- 2018-05-08 CN CN201810434199.7A patent/CN108552175A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104186470A (en) * | 2014-08-12 | 2014-12-10 | 南京金梧桐医药科技有限公司 | Application of ursolic acid to preparation of insecticide |
Non-Patent Citations (3)
| Title |
|---|
| 刘步林等: "《农药剂型加工技术》", 31 October 1998, 化学工业出版社 * |
| 郑州粮食学院: "《储粮害虫防治》", 29 February 1988, 中国商业出版社 * |
| 高鸿宾等: "《有机化学》", 31 August 1980, 化学工业出版社 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112021339A (en) * | 2019-06-03 | 2020-12-04 | 南京臻旸生物科技有限公司 | Method for preparing biological pesticide and biological fertilizer from eucalyptus leaves and eucalyptus bark and product |
| CN112142818A (en) * | 2019-06-27 | 2020-12-29 | 中国药科大学 | Oleanolic acid and oleanolic acid derivatives and medical application thereof |
| WO2020259205A1 (en) * | 2019-06-27 | 2020-12-30 | 中国药科大学 | DERIVATIVES OF OLEANOLIC ACID AND δ-OLEANOLIC ACID AND MEDICAL USE THEREOF |
| CN112142818B (en) * | 2019-06-27 | 2023-07-21 | 中国药科大学 | Derivatives of oleanolic acid and delta-oleanolic acid and medical application thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103598192B (en) | A kind of bactericidal composition containing tetramycin and Zhongshengmycin | |
| CN103385251B (en) | A kind of Pesticidal combination of pyriproxyfen-containing | |
| CN104472511A (en) | Molluscicide composition containing metaldehyde and emamectin benzoate | |
| CN108684681A (en) | A kind of mite-killing preparation and its application | |
| CN103004821A (en) | Insecticidal composition containing thiodicarb and spinosad | |
| CN103155929B (en) | Binary pesticide composition and application thereof | |
| CN108552175A (en) | The application of oleanolic acid and its derivative in preventing planthopper | |
| CN103004867B (en) | Insecticidal composition with synergism | |
| CN105340913A (en) | Sterilization composition containing benziothiazolinone and kasugamycin | |
| CN106954634A (en) | A kind of composition pesticide and its application containing pyraclonil and anilofos | |
| CN101700008B (en) | Solid lipid nano-avermectin and preparation method and application thereof | |
| CN103931630A (en) | Insecticide composition containing SYP9080 | |
| CN105340927A (en) | Sterilization composition containing benziothiazolinone and Zhongshengmycin | |
| CN104381294A (en) | Insect and mite killing composition containing xiaochongliulin and spirodiclofen | |
| CN104663687A (en) | Insecticidal and acaricidal composition containing carbamate insecticide | |
| CN104823983B (en) | Microcapsule bactericide for controlling Botrytis cinerea and Sclerotinia scleotiorum | |
| CN105724395B (en) | A kind of binary pesticide composition and its application | |
| CN106665614A (en) | Weeding composition containing penoxsulam, bispyribac-sodium and mefenacet | |
| CN106719732A (en) | Paddy rice special pesticide composition | |
| CN102165958A (en) | Pesticide composite containing bifenazate and triazophos | |
| CN103636632B (en) | A kind of Pesticidal combination containing chlorine chlorfenapyr and Aphox | |
| CN109287651A (en) | A kind of medicament composition containing Biphenthrin | |
| CN104522041A (en) | Flonicamid and efficient cyhalothrin containing insecticide composition | |
| CN108715596B (en) | Application of betulinic acid and derivatives thereof in preventing and treating rice planthopper | |
| CN108719295A (en) | A kind of molluscicide composition containing Tea Saponin |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20180921 |