CN1857079A - Extracting process for fungus metabolite for preventing and controlling weed and rice diseases and its use - Google Patents
Extracting process for fungus metabolite for preventing and controlling weed and rice diseases and its use Download PDFInfo
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Abstract
The present invention belongs to the field of microbial technology, and is especially fungus metabolite for preventing and controlling weeds and diseases of rice. The fungus metabolite contains 3-anhydroophiobollin B as compound I, phiobollin A as compound II, 3-anhydro-6-epiphiobollin A as compound III, and 3-anhydro-6-epiphiobollin B as compound IV. The preparation process includes the following steps: filtering the culture of yard grass Bipolaris sacchari to separate mycelium and fermented liquid; decompression concentrating mycelium leaching liquid to obtain the compound I concentrate; further treatment of the fermented liquid to obtain the compound II, merging the residual leaching liquid and fermented liquid and eluting to obtain compound III and compound IV mixed liquid. The fungus metabolite is used in preparing cockspur grass herbicide.
Description
Technical field
The invention belongs to microbial technology field, be specifically related to fungal metabolite extraction process that is used for controlling weeds and rice disease and uses thereof.
Background technology
The barnyard grass grass is one of the most difficult weeds of preventing and kill off in the whole world, and main at present dependence chemical herbicide is prevented and treated.Yet the long-term use of chemical herbicide makes anti-(anti-) property of medicine problem and the problem of environmental pollution of barnyard grass grass more and more serious.Develop safely and efficiently that biological weed killer meets the agricultural sustainable development requirement, though biological weed killer instead of chemical weed killer herbicide fully at present, it can effectively reduce the using dosage of chemical herbicide, thereby minimizing is to the pollution of environment.
In addition, rice sheath blight disease is seriously to restrict the global rice disease of Rice Production by soil fungi Rhizoctonia solani Kuhn (Rhizoctonia solani kuhn) class that causes.The serious regional paddy rice underproduction of falling ill can reach 50%.Owing to lack the donor of anti-banded sclerotial blight, do not bring out the rice varieties of anti-banded sclerotial blight truly at present in the world as yet, the bactericide of bactericide, especially natural origin of therefore developing highly effective and safe is particularly important.The domestic rice sheath blight disease of preventing and treating is mainly utilized jinggangmeisu at present, though jinggangmeisu is a kind of biopesticide of low toxicity, often needs repeatedly medication just can reach good control efficiency, and cost is higher.The biocontrol microorganisms of rice sheath blight disease mainly contains bacillus subtilis Pseudomonas and Pseudomonas bacterium and trichoderma fungi in the world.Utilize phytopathogen, especially weeds biocontrol microorganisms Goosegrass bipolaris (Bipolaris eleusines) is prevented and treated rice sheath blight disease and can be made full use of limited phytopathogen resource, widen screening bactericide bacterial classification scope, thereby obtain the natural bactericidal agent of highly effective and safe.Goosegrass bipolaris is Australian Alcorn ﹠amp; R.G.Shivas obtains from susceptible yard grass blade separation first, and Mycotaxon nineteen nineties 39 volume 366-370 page or leaf describe its morphological feature in detail, and type strain has been preserved in global bio-diversity information institution (Global Biodiversity Information Facility, be called for short GBIF).But the application study to it yet there are no report.The Goosegrass bipolaris bacterial classification can directly be bought from the market and obtain, and also can obtain from repeated isolation on the susceptible yard grass blade.
Summary of the invention
Technical problem to be solved by this invention is to overcome the deficiencies in the prior art, a kind of technology of extracting fungal metabolite from the Goosegrass bipolaris culture is provided, and provides fungal metabolite in preparation barnyard grass grass weed killer herbicide and the application that prevents and treats in the rice sheath blight disease agricultural chemicals.
The fungal metabolite extraction process that is used for controlling weeds and rice disease, described metabolite comprises 3-dehydration ophiobollin B (3-anhydroophiobolin B), Ophiobolin A (ophiobolin A), 3-dehydration-6-shows Ophiobolin A (3-anhydro-6-epiophiobolin A), 3-dehydration-6-shows ophiobollin B (3-anhydro-6-epiophiobolin B), below be called for short compound 1, compound 2, compound 3, compound 4 respectively, it is characterized in that comprising following processing step:
1) culture that obtains on the PDB medium with Goosegrass bipolaris (Bipolaris eleusines) is through four layers of filtered through gauze, separation of mycelial and zymotic fluid;
2) mycelium merges leaching liquor and concentrating under reduced pressure with ethyl acetate lixiviate 3 times, obtains containing the blackish green oily concentrate of compound 1;
3) zymotic fluid divides 3 extraction to half back of initial volume with equal-volume ethyl acetate at 40 ℃ of following concentrating under reduced pressure, and extraction phase adds the sepia grease that suitable quantity of water washing back concentrating under reduced pressure obtains containing compound 2;
4) will separate the mycelium extract of compound 1 and 2 and zymotic fluid extract merges, last silicagel column volume ratio is 6: 4 the n-hexane and the mixed solvent wash-out of ethyl acetate, 100mL fraction collection eluent, according to the thin-layer chromatography measurement result, after merging, the eluent that contains same composition obtains containing the wash-out mixed liquor of compound 3 and compound 4 respectively.
The described fungal metabolite extraction process that is used for controlling weeds and rice disease is characterized in that described compound 1,2,3,4 is further purified by following method respectively:
1) purifying of compound 1: mycelium lixiviate, the concentrated blackish green oily concentrate that contains compound 1 that obtains are separated out crystal after 4 ℃ of refrigeration, pass through filter paper isolated by filtration mixed crystal with Buchner funnel.Use a small amount of CHCl
3Going up silicagel column behind the dissolving crystal, is that 150: 1 the chloroform and the mixed solvent wash-out of methyl alcohol separate 10mL fraction collection eluent with volume ratio, eluent 22-25 merges the back concentrating under reduced pressure, add the chloroform dissolving, drip ethanol again and separate out colourless unsetting crystal, be compound 1.
2) purifying of compound 2: zymotic fluid concentrates the sepia grease that extraction obtains containing compound 2, and adding a little volume ratio is 1: 1 n-hexane and an ethyl acetate mixed solvent, separates out the crystal of compound 2.Method purifying with recrystallization obtains colourless acicular crystal again.
3) purifying of compound 3: containing silicagel column on the wash-out mixed liquor of compound 3, is that 250: 1 chloroform separates with methyl alcohol mixed solvent wash-out with volume ratio, and 10mL fraction collection eluent, eluent 10-12 partly merge the compound 3 that obtains red paste after concentrating.
4) purifying of compound 4: containing silicagel column on the wash-out mixed liquor of compound 4, is 150: 1 chloroform and methanol-eluted fractions with volume ratio, and eluent 15-17 merges partly that to obtain the khaki solid after concentrating be compound 4.
Test is found first after deliberation, the metabolite compound 1,2,3,4 of separation and purification from the Goosegrass bipolaris culture can be used for preparing microbial herbicide, can use separately, also can use simultaneously, thereby reduce the chemical herbicide using dosage and reach good herbicidal effect with chemical herbicide commonly used.Wherein metabolite compound 2 also can be used for preparing the biological bactericide of preventing and treating rice sheath blight disease, the control Rhizoctonia solani Kuhn.
Goosegrass bipolaris (Bipolaris eleusines) separates from susceptible yard grass and obtains, this bacterial classification and separating method are existing known technology, and but repeated isolation obtains, its cultural method also belongs to existing known technology, generally be that bacterium is inoculated in the PDB medium, under 28 ± 2 ℃ of temperature, liquid fermentation and culture 14 days.
The extraction process of above-mentioned metabolite compound is simple, has opened up new microbial herbicide and bactericide kind, and is nontoxic to people and animals, and to various crop safety such as paddy rice, the noresidue poisoning takes place, and is environmentally friendly.
Embodiment
The separation-extraction technology of compound:
1) culture that obtains on the PDB medium with Goosegrass bipolaris (Bipolaris eleusines) is through four layers of filtered through gauze, separation of mycelial and zymotic fluid;
2) mycelium merges leaching liquor and concentrating under reduced pressure with ethyl acetate lixiviate 3 times, obtains containing the blackish green oily concentrate of compound 1;
3) zymotic fluid divides 3 extraction to half back of initial volume with equal-volume ethyl acetate at 40 ℃ of following concentrating under reduced pressure, and extraction phase adds the sepia grease that suitable quantity of water washing back concentrating under reduced pressure obtains containing compound 2;
4) will separate the mycelium extract of compound 1 and 2 and zymotic fluid extract merges, last silicagel column volume ratio is 6: 4 the n-hexane and the mixed solvent wash-out of ethyl acetate, 100mL fraction collection eluent, according to the thin-layer chromatography measurement result, obtain containing the wash-out mixed liquor of compound 3 after eluent 28-36 merges, obtain containing the wash-out mixed liquor of compound 4 after eluent 37-50 merges.
The purifying process of compound: the 1) purifying of compound 1: mycelium lixiviate, the concentrated blackish green oily concentrate that contains compound 1 that obtains are separated out crystal after 4 ℃ of refrigeration, pass through filter paper isolated by filtration mixed crystal with Buchner funnel.Use a small amount of CHCl
3Going up silicagel column behind the dissolving crystal, is that 150: 1 the chloroform and the mixed solvent wash-out of methyl alcohol separate 10mL fraction collection eluent with volume ratio, eluent 22-25 merges the back concentrating under reduced pressure, add the chloroform dissolving, drip ethanol again and separate out colourless unsetting crystal, be compound 1.
2) purifying of compound 2: zymotic fluid concentrates the sepia grease that extraction obtains containing compound 2, and adding a little volume ratio is 1: 1 n-hexane and an ethyl acetate mixed solvent, separates out the crystal of compound 2.Method purifying with recrystallization obtains colourless acicular crystal again.
3) purifying of compound 3: containing silicagel column on the wash-out mixed liquor of compound 3, is that 250: 1 chloroform separates with methyl alcohol mixed solvent wash-out with volume ratio, and 10mL fraction collection eluent, eluent 10-12 partly merge the compound 3 that obtains red paste after concentrating.
4) purifying of compound 4: containing silicagel column on the wash-out mixed liquor of compound 4, is 150: 1 chloroform and methanol-eluted fractions with volume ratio, and eluent 15-17 merges partly that to obtain the khaki solid after concentrating be compound 4.
The yield of 4 kinds of compounds: from the mycelium of 16L zymotic fluid and dry weight 169.8g, separate obtaining 55mg compound 1,157mg compound 2,48mg compound 3 and 52mg compound 4.
Compound structure is identified: by analyzing nmr spectrum data and comparing the authenticating compound structure in conjunction with existing known related data.Nuclear magnetic resonance experiment mainly comprises
1H-
1H COSY, HMQC, HMBC, DEPT and NOESY, used NMR are AVANCE 500, and solvent is a deuterochloroform, and TMS is as interior mark.The used mass spectrograph of TOF-ESI-MS is Micromass LCT, and the ionization energy is 2140eV.The NMR of compound 1,2,3,4 analyzes data and is shown in Table 1.
The NMR of table 1. compound 1,2,3,4 analyzes data
| Carbon | 1 | 2 | 3 | 4 | ||||
| δ C a | δ H b | δ C | δ H | δ C | δ H | δ C | δ H | |
| 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 | 36.2 48.8 176. 131. 207. 48.3 138. 158. 27.4 52.8 46.1 38.1 33.8 86.5 39.5 | α1.91(m) β1.38(m) 3.19(d，4.5) - 6.11(s) - 4.13(d，7.1) - 7.07(dd，7.1 α2.73(m) β2.45(m) 2.27(s) - α1.78(m) β1.25(m) α1.38(m) β1.64(m) - 1.41(m) | 36.0 51. 0 77.0 55.6 217. 49.1 142. 163. 24.3 61.3 43.4 41.6 30.9 95.4 37.6 | ～1.71(m) 2.36(ddd，12.9，1 - α2.81(d，19.2) β2.50(d，19.2) 3.26(d，10.6) - 7.21(t，8.6) α β2.25(m) 1.76(m) - α1.73(m) β α1.63(m) β2.04(m) - 2.18(m) | 46. 49. 177 130 207 49. 141 155 29. 53. 42. 41. 30. 96. 35. | α1.42(m) β 2.65(d，3.5) - 6.02(t，1.4) - 3.42(d，4.0) - 6.81(dd，6.5，2 α β2.35(m) 2.67(d，3.8) - ～1.42(m) α1.60(m) β1.68(m) - 2.23(m) | 46.1 48.8 177. 130. 207. 49.8 140. 155. 31.5 54.5 44.7 41.4 35.2 88.3 37.1 | α1.34(m) β2.10(m) 2.68(d，13) - 6.04(s) - 3.45(d，4.2) - 6.78(dd，6.3，2. α β2.10(m) 2.56(dd，4.3，2. - α2.00(m) β1.45(m) α1.45(m) β1.59(m) - 1.45(m) |
| 16 17 18 19 20 21 22 23 24 25 | 32.7 26.3 124. 131. 18.5 194. 23.6 16.1 17.7 25.7 | 1.00(m) 1.66(m) 1.90(m) 2.08(m) 5.09(dd，7.1 - 2.23(s) 9.41(s) 0.78(s) 0.89(d，6.7) 1.60(s) 1.69(s) | 43.9 71.6 126. 137. 26.3 196. 18.6 18.9 18.9 26.6 | 1.67(m) 1.77(m) 4.43(m) 5.15(dt，8.6，1.3 - 1.37(s) 9.24(s) 0.82(s) 1.09(d，7.2) 1.71(d，1.1) 1.74(d，1.1) | 42. 72. 126 135 17. 192 22. 16. 18. 25. | 1.72(m) 1.78(m) 4.59(dd，15.6， 5.13(ddd，8.6， - 2.04(s) 9.31(s) 0.87(s) 1.04(d，6.9) 1.65(d，1.0) 1.70(d，0.9) | 32.6 26.2 124. 132. 17.1 192. 22.5 14.8 17.7 25.7 | 1.20(m) 1.47(m) 1.98(m) 2.12(m) 5.16(d，7.3) - 2.07(s) 9.32(s) 0.88(s) 0.98(d，6.6) 1.63(s) 1.71(s) |
aChemical shift in chloroformic solution 125 hertz the time;
bCoupling constant and multiplicity in the time of 500 hertz.
By labor NMR spectral data and TOF-ESI-MS spectrogram, determined that the structural formula of compound 1,2,3,4 is respectively: compound 1:3-dehydration ophiobollin B, English name 3-anhydroophiobolin B (1); Compound 2: Ophiobolin A, English name ophiobolin A (2); Compound 3:3-dehydration-6-shows Ophiobolin A, English name 3-anhydro-6-epiophiobolin A (3); Compound 4:3-dehydration-6-table ophiobollin B, English name 3-anhydro-6-epiophiobolin B (4).
1：R＝βH，3-anhydroophiobolin B 2：Ophiobolin A 3：3-anhydro-6-epiophiobolin A
4：R＝αH，3-anhydro-6-epiophiobolin
B
Compound 2 (ophiobolin A) removing activity and to the biologicall test of rice safety evaluation:
Select for use with a collection of barnyard grass grass seed and japonica rice show water 11, early long-grained nonglutinous rice 03-133 and hybrid rice 187 (representing japonica rice, long-grained nonglutinous rice and hybrid rice respectively), behind presoaking and germinating, select 10 the long 2mm of root left and right sides vernalization seeds and put into the diameter 7cm culture dish (filter paper in ware shop) that is added with measured matter solution (is 0.1% to the DMSO final concentration with micro-DMSO dissolving back thin up), with 0.1%DMSO is blank, put in the incubator and cultivated 2 days down, measure root length and calculate the root growth inhibiting rate in 27 ± 1 ℃.The gained result carries out variance analysis (p＜0.05), estimates IC according to the inhibiting rate that records
50Value.The measured matter sample is chosen 3 concentration gradients, is respectively 10,100,1000 μ g/mL, selects 2 for use, and the 4-D conduct is over against photograph.Result of the test shows: compound 2 (ophiobolin A) has strong inhibitory action, its IC to barnyard grass grass seed radicle growth in the culture dish bioassay
50Value is 7.5 μ M.Experiment find the barnyard grass grass than paddy rice to compound 2 (opbiobolin A) responsive (seeing Table 2) more.Different rice varieties are different to the susceptibility of compound 2 (ophiobolinA), but all do not surpass the barnyard grass grass.Show that Goosegrass bipolaris and metabolite compound 2 thereof (ophiobolin A) have the potentiality of exploitation barnyard grass grass biological weed killer.
Table 2:ophiobolin A is to barnyard grass grass and the long IC of different rice varieties roots
50Value (μ M)
| Kind | IC 50Value (μ M) |
| Elegant water 11 (japonica rice) early rice 03-133 (long-grained nonglutinous rice) (indica hybrid rice 187 (hybrid rice) (hybrid barnyard grass grass | 31 175 150 7.5 |
The biologicall test of compound 1 (3-anhydroophiobolin B), compound 3 (3-anhydro-6-epiophiobolin A) and compound 4 (3-anhydro-6-epiophiobolin B) removing activity
Bioassay method is with compound 2, and result of the test shows the IC of compound 1
50Value is 208 μ M, the IC of compound 3
50Value is 785 μ M, the IC of compound 4
50Value is 260 μ M, and the barnyard grass grass is also had apparent in view inhibition activity.
Compound 2 (ophiobolin A) bactericidal activity detects
Get compound 2 (ophiobolin A) and dissolve with micro-DMSO, adding water, to regulate its concentration be 1mg/mL (containing 0.1%DMSO), and 0.22 μ m filtering with microporous membrane gets aseptic toxin soiutions.With fusing and be cooled to 45～50 ℃ PDA medium and regulate its toxin concentration and be respectively 50,25,10,5 and 1 μ g/mL (2.5 μ M).Add the 2.5mL0.1%DMSO aqueous solution in the contrast PDA medium.Other establishes jinggangmeisu (5%) active ingredient 200,100,50,25,10 μ g/mL is the bactericide contrast.Be inoculated in above-mentioned dull and stereotyped central authorities from cut-off footpath, the banded sclerotial blight bacterium colony edge 7mm bacterium piece of cultivating 2d, cultivate 24h for 28 ℃, survey colony diameter with the right-angled intersection method, and be calculated as follows the inhibiting rate of 2 pairs of sheath blight fungus of compound.
Result of the test demonstration compound 2 (ophiobolin A) is all compared according to jinggangmeisu (seeing Table 3) eager to excel in whatever one does sheath blight fungus mycelial growth inhibitory action activity, compound 2 (ophiobolin A) then just has 100% inhibitory action under 25 μ g/mL concentration, and 5% jinggangmeisu can only reach 45.2% inhibiting rate when active ingredient concentration is 200 μ g/mL.As seen barnyard grass grass Bipolaris sacchari metabolite compound 2 (ophiobolin A) have fabulous bacteriostasis to Rhizoctonia solani Kuhn, and its fungistatic effect obviously is better than jinggangmeisu commonly used at present, can develop as biological bactericide.
Table 3: compound 2 (ophiobolin A) is to sheath blight fungus mycelial growth inhibitory action
| Bacteriostatic agent | Inhibiting rate (%) | |||||
| 200 a | 100 | 50 | 25 | 10 | 1 | |
| Ophiobolin A jinggangmeisu | - c 45.2 | - 29.4 | 100 22.6 | 100 11.3 | 85.9 7.9 | 70.2 - |
aThe bacteriostatic agent concentration unit is μ g/mL;
bShown in inhibiting rate be the mean value of twice reproducible results, variance analysis p＜0.05;
c"-" expression does not detect.
Claims (4)
1, the fungal metabolite extraction process that is used for controlling weeds and rice disease, described metabolite comprises 3-dehydration ophiobollin B (3-anhydroophiobolin B), Ophiobolin A (ophiobolin A), 3-dehydration 6-table Ophiobolin A (3-anhydro-6-epiophiobolin A), 3-dehydration-6-shows ophiobollin B (3-anhydro-6-epiophiobolin B), below be called for short compound 1, compound 2, compound 3, compound 4 respectively, it is characterized in that comprising following processing step:
1) culture that Goosegrass bipolaris (Bipolaris eleusines) is obtained on the PDB medium is through four layers of filtered through gauze, separation of mycelial and zymotic fluid;
2) mycelium merges leaching liquor and concentrating under reduced pressure with ethyl acetate lixiviate 3 times, obtains containing the blackish green oily concentrate of compound 1;
3) zymotic fluid divides 3 extraction to half back of initial volume with equal-volume ethyl acetate at 40 ℃ of following concentrating under reduced pressure, and extraction phase adds the sepia grease that suitable quantity of water washing back concentrating under reduced pressure obtains containing compound 2;
4) will separate the mycelium extract of compound 1 and 2 and zymotic fluid extract merges, last silicagel column volume ratio is 6: 4 the n-hexane and the mixed solvent wash-out of ethyl acetate, 100mL fraction collection eluent, according to the thin-layer chromatography measurement result, after merging, the eluent that contains same composition obtains containing the wash-out mixed liquor of compound 3 and compound 4 respectively.
2, the fungal metabolite extraction process that is used for controlling weeds and rice disease as claimed in claim 1 is characterized in that described compound 1,2,3,4 is further purified by following method respectively:
1) purifying of compound 1: mycelium lixiviate, the concentrated blackish green oily concentrate that contains compound 1 that obtains are separated out crystal after 4 ℃ of refrigeration, pass through filter paper isolated by filtration mixed crystal with Buchner funnel.With going up silicagel column behind a small amount of CHCl3 dissolving crystal, be that 150: 1 the chloroform and the mixed solvent wash-out of methyl alcohol separate 10mL fraction collection eluent with volume ratio, eluent 22-25 merges the back concentrating under reduced pressure, add the chloroform dissolving, drip ethanol again and separate out colourless unsetting crystal, be compound 1.
2) purifying of compound 2: zymotic fluid concentrates the sepia grease that extraction obtains containing compound 2, and adding a little volume ratio is 1: 1 n-hexane and an ethyl acetate mixed solvent, separates out the crystal of compound 2.Method purifying with recrystallization obtains colourless acicular crystal again.
3) purifying of compound 3: the chloroform that contains tlc silica gel post H volume ratio on the wash-out mixed liquor of compound 3 and be 250: 1 separates with methyl alcohol mixed solvent wash-out, 10mL fraction collection eluent, eluent 10-12 partly merge the compound 3 that obtains red paste after concentrating.
4) purifying of compound 4: contain tlc silica gel post H volume ratio on the wash-out mixed liquor of compound 4 and be 150: 1 chloroform and methanol-eluted fractions, eluent 15-17 merges partly that to obtain the khaki solid after concentrating be compound 4.
3, the application of fungal metabolite as claimed in claim 1 or 2 in preparation barnyard grass grass weed killer herbicide.
4, fungal metabolite as claimed in claim 1 or 2 is prevented and treated application in the rice sheath blight disease agricultural chemicals in preparation.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100593567C (en) * | 2006-12-22 | 2010-03-10 | 中国水稻研究所 | Culture process of yard grass Bipolaris sacchari and its use |
| CN103172507A (en) * | 2011-12-21 | 2013-06-26 | 中国科学院微生物研究所 | Ophiobollin sesterterpine compound as well as preparation method and application thereof |
| CN104920479A (en) * | 2015-07-10 | 2015-09-23 | 上海万力华生物科技有限公司 | Herbicide and preparation method and application thereof |
| CN109503613A (en) * | 2018-11-28 | 2019-03-22 | 中南民族大学 | Goosegrass bipolaris element I and the preparation method and application thereof, Goosegrass bipolaris element J and the preparation method and application thereof |
| CN112120034A (en) * | 2020-09-17 | 2020-12-25 | 中国科学院南海海洋研究所 | Application of 6-R-ophiosporin G in preparation of marine fouling organism control agent |
| CN112120033A (en) * | 2020-09-17 | 2020-12-25 | 中国科学院南海海洋研究所 | Application of ophiosporin G in preparation of marine fouling organism control agent |
-
2006
- 2006-06-06 CN CNB2006100518317A patent/CN100356852C/en not_active Expired - Fee Related
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100593567C (en) * | 2006-12-22 | 2010-03-10 | 中国水稻研究所 | Culture process of yard grass Bipolaris sacchari and its use |
| CN103172507A (en) * | 2011-12-21 | 2013-06-26 | 中国科学院微生物研究所 | Ophiobollin sesterterpine compound as well as preparation method and application thereof |
| CN104920479A (en) * | 2015-07-10 | 2015-09-23 | 上海万力华生物科技有限公司 | Herbicide and preparation method and application thereof |
| CN104920479B (en) * | 2015-07-10 | 2018-07-10 | 上海万力华生物科技有限公司 | A kind of herbicide and its preparation method and application |
| CN109503613A (en) * | 2018-11-28 | 2019-03-22 | 中南民族大学 | Goosegrass bipolaris element I and the preparation method and application thereof, Goosegrass bipolaris element J and the preparation method and application thereof |
| CN112120034A (en) * | 2020-09-17 | 2020-12-25 | 中国科学院南海海洋研究所 | Application of 6-R-ophiosporin G in preparation of marine fouling organism control agent |
| CN112120033A (en) * | 2020-09-17 | 2020-12-25 | 中国科学院南海海洋研究所 | Application of ophiosporin G in preparation of marine fouling organism control agent |
| CN112120033B (en) * | 2020-09-17 | 2021-11-09 | 中国科学院南海海洋研究所 | Application of ophiosporin G in preparation of marine fouling organism control agent |
| CN112120034B (en) * | 2020-09-17 | 2021-11-09 | 中国科学院南海海洋研究所 | Application of 6-R-ophiosporin G in preparation of marine fouling organism control agent |
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| Publication number | Publication date |
|---|---|
| CN100356852C (en) | 2007-12-26 |
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