CN101037442A - New compound prepared by ice city streptomyces and preparation method - Google Patents
New compound prepared by ice city streptomyces and preparation method Download PDFInfo
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- CN101037442A CN101037442A CN 200710071652 CN200710071652A CN101037442A CN 101037442 A CN101037442 A CN 101037442A CN 200710071652 CN200710071652 CN 200710071652 CN 200710071652 A CN200710071652 A CN 200710071652A CN 101037442 A CN101037442 A CN 101037442A
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Abstract
The invention provides a new compound-alpha milbemycins produced by BingCheng streptomyces spp. and the preparing method. The compound are three new compound separated from the BingCheng Streptomyces spp. The preparing method comprises seed culture and liquid fermentation, which includes filtering the liquid fermentation, extracting with carbinol, EtOAc extraction, concentrating, silica gel column chromatography, RP-18 column chromatography to get the target compound. The inventive new compound has a strong activity to kill acarid and also can be used to control other insects harmful to the plants.
Description
Technical field
What the present invention relates to is a kind of compound, specifically a kind of α series mibemycin.The invention still further relates to the preparation method of this compound.
Background technology
At present, domestic and international application Macrolide agricultural antibiotic Avrmectin widely belongs to the disaccharide compounds, and 50% of domestic annual production is used for outlet.Avrmectin contains avermectin B1a 〉=80% and avermectinB1b≤20%, and phytophagous mites is had special efficacy, by exploitation of U.S. Merck company and production, has and tags and stomach poison function, and very weak interior absorption is arranged.Can prevent and treat evil mites such as tangerine edge mite, ordinary maple leaf mite, elm Panonychus citri and two-spotted spider mite, be mainly used in the harmful mite on the crops such as control cotton, citrus, nut, vegetables, potato, ornamental plant, to natural enemies security, harmful mite to the active phase all has activity, but it is to the rudimentary nontoxic effect of killing of just laying eggs of embryo, and only the later stage ovum that the embryo has been grown has strong ovicidal activity.
Summary of the invention
The purpose of this invention is to provide a kind of insect and have the active new compound-α type mibemycin of very high inhibition with the preparation of Harbin streptomycete to acarid and other infringement plants.
Another object of the present invention provides the preparation method of the new compound-α type mibemycin of Harbin streptomycete preparation.
The structural formula of compound of the present invention is:
Wherein R1 can be CH
3Or CH
2CH
3R
2Can be:
Or
R
3Can be:
Or H.
Its concrete unitized construction can for:
Product of the present invention is to adopt such method to prepare:
(1) fermentation strain: the classification called after Harbin streptomycete (Streptomyces bingchengsis sp.nov) of fermented bacterium, be preserved on 06 12nd, 2006 that " Chinese biological culture presevation management committee common micro-organisms " center ", its preservation registration number is: CGMCC NO.1734.And landing 16S rDNA sequence at NCBI, sequence number is DQ449953.
(2) slant culture: sucrose with 0.4%, 0.2% yeast powder, 0.5% malt extract, 0.1% and skim-milk, soluble in water, transfer pH to 7.0 with 1mol NaOH, add 2.0% agar, transfer the back 121 ℃ of sterilization 30min of pH to 7.2 again, cultivated 7-8 days for 28 ℃, the Harbin streptomycete spore on inclined-plane is washed and make spore suspension with the 1ml sterilized water.
(3) seed culture: substratum (sucrose 1%; Albumen freezes 0.4%; K
2HPO
40.05%.With every bottle of packing 25ml of triangular flask of 250ml, the 1ml spore suspension is added in the 25ml seed culture medium, place on the shaking table 28 ℃, 250rpm cultivates 42h then with substratum (sucrose 8%; Soybean-cake flour 1%; Yeast powder 0.2%; Extractum carnis 0.1%; CaCO
30.3%; K
2HPO
40.3%, MgSO
47H
2O 0.1%, FeSO
47H
2O 0.005%; Adjusting pH to 7.2) every 100ml is sub-packed in the 1L triangular flask, 121 ℃ of sterilization 30min, and inoculation 8ml contains the seed culture medium of spore suspension, and as for 28 ℃ of shaking tables, 250rpm cultivated 8 days.
(4) fermentation liquor treatment: the 50L fermented liquid filters through 200 eye mesh screens, and water cleans fermented liquid, the water of fermented liquid and cleaning usefulness all discards, with the filter residue that obtains after 30 liters of methyl alcohol lixiviates filtrations, method by underpressure distillation is concentrated to methanol solution about 2 liters at last, again with concentrated solution with the EtOAc lixiviate of equal volume 3 times, with the EtOAc phase that obtains, the underpressure distillation meeting produces the 25g oily mater.Silicagel column on the gained oily matter (particle diameter 200～300 orders) is carried out chromatography, use sherwood oil respectively: (95: 5-50: 50) wash-out, distillation is not contained the raw product 10g of A3 and A4 to acetone.Raw product is used sherwood oil respectively: (9: 1-3: 1) two kinds of elutriants carry out wash-out to acetone, have obtained five components, with RP-C on the component four
18Silicagel column carries out chromatography, uses methyl alcohol: water=70: 30-85: 15 2 kinds of elutriants carry out wash-out, can obtain compound 1 (20mg) and compound 2 (11mg).With RP-C on the component three
18Silicagel column carries out chromatography, uses methyl alcohol: (70: 30-95: 5) wash-out obtains compound 3 22mg to water.
Compound of the present invention has strong acaricidal activity, can kill, and what for example colonize in that fruit tree, vegetables and the Tetranychus of taking, Panonychus citri belong to and rust mite belongs to becomes mite and ovum.They also have activity for parasitizing animal hard tick section, Dermanyssidae and Sarcoptidae on one's body.They can also be killed: epizoon, as parasitize animal and bird, especially livestock and poultry Oestrus, Lucilia, Hypoderma, Gasterophilus on one's body, lice and flea; The family insect is as cockroach and housefly; And the various harmful insects in agricultural and the gardening ground, as aphid and lepidopterous larvae.The mole cricket that they also can effectively be killed in the soil belongs to.They also can effectively kill the insect of following kind: Coleoptera, Homoptera, Heteroptera, Diptera, Thysanoptera, Orthoptera, Anoplura, Siphonaptera, Mallophaga, Thysanura, Isoptera, Hymenoptera etc.
Compound of the present invention equally can be in order to control the insect that other can damage plant, especially by eating the insect that plant makes it to damage.These compounds can be in order to protection ornamental plant and productivity plant, especially cotton (as killing Heliothis virescens), and vegetable crop (as killing colorado potato bug and black peach aphid) and rice crop (as killing striped rice borer and rice lice).
New compound of the present invention not only has the effect of well killing adult, and is also very high to the worm's ovum drug effect, therefore, has more potentiality to be exploited.
Description of drawings
Fig. 1 Mil shellfish α
23The inv4gplrndqf spectrogram;
Fig. 2 Mil shellfish α
23The cosygpqf spectrogram;
Fig. 3 Mil shellfish α
23The inv4gplrndqf spectrogram;
Fig. 4 Mil shellfish α
23The invietgp spectrogram;
Fig. 5 Mil shellfish α
23The ms spectrogram;
Fig. 6 Mil shellfish α
23The zgdc spectrogram;
Fig. 7 Mil shellfish α
24The noesyph spectrogram;
Fig. 8 Mil shellfish α
24The invietgp spectrogram;
Fig. 9 Mil shellfish α
24The cosygpqf spectrogram;
Figure 10 Mil shellfish α
24The zgdc spectrogram;
Figure 11 Mil shellfish α
24Zgdc spectrogram Mil shellfish α
24The zg30 spectrogram;
Figure 12 Mil shellfish α
24The ms spectrogram;
Figure 13 Mil shellfish α
24The inv4gplrndqf spectrogram;
Figure 14 Mil shellfish α
25The noesyph spectrogram;
Figure 15 Mil shellfish α
25The inv4gplrndqf spectrogram;
Figure 16 Mil shellfish α
25The invietgp spectrogram;
Figure 17 Mil shellfish α
25The zgdc spectrogram;
Figure 18 Mil shellfish α
25The zg30 spectrogram.
Embodiment
Below in conjunction with embodiment, the present invention is elaborated.
Embodiment 1: compound
1. fermentation
(1) fermentation strain: the classification called after Harbin streptomycete (Streptomyces bingchengsis sp.nov) of fermented bacterium, be preserved on 06 12nd, 2006 that " Chinese biological culture presevation management committee common micro-organisms " center ", its preservation registration number is: CGMCC NO.1734.And landing 16S rDNA sequence at NCBI, sequence number is DQ449953
(2) slant culture: sucrose with 0.4%, 0.2% yeast powder, 0.5% malt extract, 0.1% and skim-milk, soluble in water, transfer pH to 7.0 with 1mol NaOH, add 2.0% agar, transfer the back 121 ℃ of sterilization 30min of pH to 7.2 again, cultivated 7-8 days for 28 ℃, the Harbin streptomycete spore on inclined-plane is washed and make spore suspension with the 1ml sterilized water.
(3) seed culture: substratum (sucrose 1%; Albumen freezes 0.4%; K
2HPO
40.05%.With every bottle of packing 25ml of triangular flask of 250ml, the 1ml spore suspension is added in the 25ml seed culture medium, place on the shaking table 28 ℃, 250rpm cultivates 42h then with substratum (sucrose 8%; Soybean-cake flour 1%; Yeast powder 0.2%; Extractum carnis 0.1%; CaCO
30.3%; K
2HPO
40.3%, MgSO
47H
2O 0.1%, FeSO
47H
2O 0.005%; Adjusting pH to 7.2) every 100ml is sub-packed in the 1L triangular flask, 121 ℃ of sterilization 30min, and inoculation 8ml contains the seed culture medium of spore suspension, and as for 28 ℃ of shaking tables, 250rpm cultivated 8 days.
(4) fermentation liquor treatment: the 50L fermented liquid filters through 200 eye mesh screens, and water cleans fermented liquid, the water of fermented liquid and cleaning usefulness all discards, with the filter residue that obtains after 30 liters of methyl alcohol lixiviates filtrations, method by underpressure distillation is concentrated to methanol solution about 2 liters at last, again with concentrated solution with the EtOAc lixiviate of equal volume 3 times, with the EtOAc phase that obtains, the underpressure distillation meeting produces the 25g oily mater.Silicagel column on the gained oily matter (particle diameter 200～300 orders) is carried out chromatography, use sherwood oil respectively: (95: 5-50: 50) wash-out, distillation is not contained the raw product 10g of A3 and A4 to acetone.Raw product is used sherwood oil respectively: (9: 1-3: 1) two kinds of elutriants carry out wash-out to acetone, have obtained five components, with RP-C on the component four
18Silicagel column carries out chromatography, uses methyl alcohol: water=70: 30-85: 15 2 kinds of elutriants carry out wash-out, can obtain compound 1 (20mg) and compound 2 (11mg).With RP-C on the component three
18Silicagel column carries out chromatography, uses methyl alcohol: (70: 30-95: 5) wash-out obtains compound 3 22mg to water.
2 structures are identified
Mil shellfish α
23(1) molecular formula: C
41H
55NO
12
States of matter: white powder;
Ultimate analysis: C 65.34% H 7.30% O 25.50%
[α]
20 D-12 ° of (c0.65, CHCl
3); V (MeOH) λ
MaxNm (log ε): 246 (3.32); R (KBr), v
MaxCm
-1: 3425 (OH), 2926,1716,1649,592,1458,1415,1377,1261,1034,802,756,665;
1H NMR (CDCl
3, 400MHz) and
13C-NMR (CDCl
3, 100MHz) data are referring to table 1; ESIMS m/z 771[M+NH
4]
+HRESIMS m/z 771.2303[(M+NH
4)
+, calcd for C
41H
59N
2O
12, 771.2273].
Mil shellfish α
24(2) molecular formula: C
43H
59NO
12
States of matter: white powder;
Ultimate analysis: C 66.07% H 7.55% O 24.58%[α]
20 D-12 ° of (c0.65, CHCl
3); UV (MeOH) λ
MaxNm (log ε): 246 (3.32); IR (KBr), v
MaxCm
-1: 3425 (OH), 2926,1716,1649,1592,1458,1415,1377,1261,1034,802,756,665;
1H NMR (CDCl
3, 400MHz) and
13C-NMR (CDCl
3, 100MHz) data are referring to table 1; ESIMS m/z 799[M+NH
4]
+HRESIMS m/z 799.2303[(M+NH
4)
+, calcd for C
43H
63N
2O
12, 799.2273].
Mil shellfish α
25(3) molecular formula: C
37H
54O
10
States of matter: white powder;
Ultimate analysis: C 71.84% H 8.74% O 19.42%[α]
20 D-12 ° (c 0.65, CHCl
3); UV (MeOH) λ
MaxNm (log ε): 246 (3.32); IR (KBr), v
MaxCm
-1: 3425 (OH), 2926,1716,1649,1592,1458,1415,1377,1261,1034,802,756,665;
1H NMR (CDCl
3, 400MHz) and
13C-NMR (CDCl
3, 100MHz) data are referring to table 1; ESIMS m/z 657[M-H]
+HRESIMS m/z 657.2303[(M-H)
+, calcd for C
37H
53O
10, 657.2273].
Table 1: Mil shellfish α
23(1), α
24(2), α
25(3)
1H-and
13The data of CNMR (being coupling constant in the bracket)
| | Proton | Carbon | |||||||
| 1 | 2 | 3 | 1 | 2 | 3 | ||||
| 1 2 3 4 | 3.36br s 5.80br s | 3.37br s 5.82br s | 3.28br s 5.42br s | 172.9s * 45.6d 121.7d 136.5s | 172.9s * 45.7d 121.7d 136.6s | 173.5s * 45.7d 118.1d 137.9s | |||
| 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 | 4.55d(6.0) 4.01d(6.0) 5.80d(11.3) 5.76dd(14.0，11.3) 5.38dd(14.0，10.0) 2.45m 2.24m 1.93m 4.98m 2.24m 3.65m 1.86m 0.91m 5.33m 1.93m 3.22br t(8.8) 4.93m 1.55m 3.45m | 4.55d(6.0) 4.01d(6.0) 5.82d(11.2) 5.77dd(14.0，11.2) 5.38dd(14.0，10.0) 2.44m 2.23m 1.89m 4.97m 2.25m 3.63m 1.85m 0.93m 5.33m 1.93m 3.24br t(8.8) 4.93m 1.57m 3.44m | 4.32d(6.6) 3.97d(6.6) 5.79d(11.3) 5.77dd(14.5，11.3) 5.38dd(14.5，10.0) 2.43m 2.20m 1.88m 4.94m 2.24m 3.61m 1.83m 0.93m 5.34m 1.92m 3.22m 4.94m 1.64m 3.22m | 64.7d 79.2d 80.4s 139.1s 120.6d 123.4d 143.1d 36.0d 48.5t 137.5s 120.3d 34.7t 68.5d 36.2t 68.5d 36.1t 100.0s 75.4d 75.4d 42.2d 69.3d | 64.8d 79.3d 80.4s 139.2s 120.6d 123.3d 143.0d 36.0d 48.5t 137.4s 120.4d 34.8t 68.5d 36.1t 68.4d 36.0t 100.0s 75.4d 75.5d 42.3d 69.4d | 67.7d 79.2d 80.2s 139.6s 120.3d 123.4d 142.8d 35.9d 48.5t 137.5s 120.3d 34.5t 68.5d 36.2t 68.0d 36.3t 99.8s 75.4d 75.4d 39.9d 73.7d |
| 26 27 28 29 30 31 32 33 34 35 36 1’ 2’ 3’ 4’ 5’ 6’ 7’ | 4.98d(13.4) 4.88d(13.4) 4.71br s 1.02d(6.7) 1.55br s 0.84d(6.5) 1.22d(6.2) 6.97d(5.8) 6.27dd(5.8，2.9) 6.98t(2.9) 2.45m 1.71m 1.52m 0.95t(7.4) 1.19d(7.0) | 4.99d(13.4) 4.87d(13.4) 4.71br s 1.03d(6.7) 1.56br s 0.85d(6.5) 1.23d(6.2) 6.97d(5.8) 6.27dd(5.8，2.9) 6.98t(2.9) 2.59m 1.65m 1.23m 1.65m 0.90d(7.0) 1.18d(7.0) 0.88d(7.0) | 1.88s 4.87d(13.4) 4.70d(14.5) 4.66d(14.5) 1.01d(6.8) 1.55br s 0.84d(6.6) 1.75m 1.45m 1.03t(6.8) 2.43m 1.75m 1.50m 0.95t(7.5) 1.19d(6.9) | 64.2t 68.4t 22.3q 15.6q 13.0q 18.8q 160.9s 122.2s 116.0d 110.5d 123.4d 177.5s 41.5d 26.8t 11.6q 16.8q | 64.1t 68.4t 22.2q 15.5q 13.0q 18.8q 160.8s 122.3s 115.9d 110.5d 123.4d 177.8s 38.0d 42.9t 25.9d 22.5q 17.7q 22.6q | 19.9q 68.4t 22.3q 15.6q 12.7q 25.1t 9.9q 177.5s 41.6d 26.8t 11.7q 16.8q |
3. anti-insect activity measuring method
(1) activity of anti-adult mite class
0.1% methanol solution of test compound is diluted 10 times to make the solution of 100 μ g/ml with the water that contains 0.01% stain remover.Be mixed with the test liquid of different concns again, be respectively 100 μ g/ml, 50 μ g/ml, 30 μ g/ml, 10 μ g/ml.
Experiment will be infected Kidney bean plant primary blades to the Tetranychus urticae of organophosphorus insecticides sensitivity, after one day, the blade that infects Tetranychus urticae will be immersed in the testing liquid 1-2s that configures.Allow plant strain growth three days at 25 ℃, calculate mite class mortality ratio with microscopic examination.
(2) activity of anti-mite class worm's ovum
To be made into 100 μ g/ml respectively for testing compound solution, 50 μ g/ml, 30 μ g/ml, 10 μ g/ml infect the Kidney bean primary blades with female Tetranychus urticae.Again adult is removed after on the observation blade 40 ovum being arranged probably.The blade that infects Tetranychus urticae is immersed in the testing liquid 1-2s that configures.Allow plant strain growth ten days at 25 ℃, calculate the ratio that does not grow up to adult, i.e. its mortality ratio.
(3) nematicide activity
0.1% methanol solution of test compound is diluted 10 times to make the solution of 100 μ g/ml with the water that contains 0.01% stain remover.Be mixed with the test liquid of different concns again, be respectively 100 μ g/ml, 50 μ g/ml, 30 μ g/ml, 10 μ g/ml.
The solution for preparing is added 1ml contain in the aqueous suspensions of living nematode, mix back 25 ℃, placed 15 hours, nematode is no longer movable, uses stereoscopic microscope observing.The inactive ratio of nematode, i.e. its mortality ratio.
4. determination of activity result
Three kinds of new compound Mil shellfish α
23, α
24And α
25, have the powerful activity of killing acarid and nematode, see Table 2,3.Experiment showed, that the Mil shellfish rhzomorph activity known to these new compounds ratios in the past is stronger.In general, α type mibemycin is active stronger than β type.But more highly active work in-process are still in constantly studying.
Table 2. Mil shellfish new compound is killed the activity of Tetranychus urticae adult and worm's ovum
| Concentration (μg/ml) | Adult mortality ratio (%) | Worm's ovum mortality ratio (%) | ||||||
| α 23 | α 24 | α 25 | A 3/A 4 * | α 23 | α 24 | α 25 | A
3/ | |
| 100 | 91.2 | 96.5 | 100 | 73.4 | 87.9 | 43.5 | ||
| 50 | 58.7 | 69.3 | 100 | 43,5 | 67.1 | 17.3 | ||
| 30 | 17.3 | 37.4 | 93.0 | 13.7 | 12.4 | 4.1 | ||
| 10 | 5.4 | 11.2 | 71.4 | 0 | 3.4 | |||
Table 3. Mil shellfish new compound is killed the activity of nematode
| Concentration (μ g/ml) | Mortality ratio (%) | |||
| α 23 | α 24 | α 25 | A
3/ | |
| 100 | 100 | 100 | 100 | |
| 50 | 76 | 87 | 100 | |
| 30 | 53 | 54 | 91 | |
| 10 | 21 | 31 | 74 | |
*Mil shellfish A3 and A4 mixes (30: 70)
Claims (5)
1, a kind of new compound with the preparation of Harbin streptomycete, it is characterized in that: structural formula is:
Wherein R1 can be CH
3Or CH
2CH
3R
2Can be:
Or
R
3Can be:
Or H.
2, the new compound with the preparation of Harbin streptomycete according to claim 1 is characterized in that: the R of compound 1
1Be CH
3, R
2Be
R
3Be
3, the new compound with the preparation of Harbin streptomycete according to claim 1 is characterized in that: the R of compound 2
1Be CH3, R
2Be
R
3Be
4, the new compound with the preparation of Harbin streptomycete according to claim 1 is characterized in that: the R of compound 3
1Be CH
2CH
3, R
2Be
R
3Be H.
5, a kind of preparation method who uses the new compound of Harbin streptomycete preparation is characterized in that:
(1) fermentation strain: fermented bacterium is the Harbin streptomycete;
(2) slant culture: sucrose with 0.4%, 0.2% yeast powder, 0.5% malt extract, 0.1% and skim-milk, soluble in water, transfer pH to 7.0 with 1mol NaOH, add 2.0% agar, transfer the back 121 ℃ of sterilization 30min of pH to 7.2 again, cultivated 7-8 days for 28 ℃, the Harbin streptomycete spore on inclined-plane is washed and make spore suspension with the 1ml sterilized water;
(3) seed culture: substratum consists of that sucrose 1%, albumen freeze 0.4%, K
2HPO
40.05%, with every bottle of packing 25ml of triangular flask of 250ml, the 1ml spore suspension is added in the 25ml seed culture medium, place on the shaking table 28 ℃, 250rpm cultivates 42h; Then weight ratio is consisted of sucrose 8%, soybean-cake flour 1%, yeast powder 0.2%, extractum carnis 0.1%, CaCO
30.3%, K
2HPO
403%, MgSO
47H
2O 0.1% and FeSO
47H
2The substratum of O 0.005% is regulated pH to 7.2, and every 100ml is sub-packed in the 1L triangular flask, 121 ℃ of sterilization 30min, and inoculation 8ml contains the seed culture medium of spore suspension, and as for 28 ℃ of shaking tables, 250rpm cultivated 8 days;
(4) fermentation liquor treatment: the 50L fermented liquid filters through 200 eye mesh screens, and water cleans fermented liquid, the water of fermented liquid and cleaning usefulness all discards, with the filter residue that obtains after 30 liters of methyl alcohol lixiviates filtrations, method by underpressure distillation is concentrated to methanol solution 2 liters at last, again with concentrated solution with the EtOAc lixiviate of equal volume 3 times, with the EtOAc phase that obtains, the underpressure distillation meeting produces the 25g oily mater; Silicagel column on the gained oily matter is carried out chromatography, use sherwood oil respectively: 95 of acetone: 5-50: 50 mixture wash-out, distillation is not contained the raw product 10g of A3 and A4; Raw product is used sherwood oil respectively: 9 of acetone: 1-3: 1 mixture elutriant carries out wash-out, has obtained five components, with RP-C on the component four
18Silicagel column carries out chromatography, uses methyl alcohol: water=70: 30-85: 15 elutriants carry out wash-out, can obtain compound 1,20mg and compound 2,11mg; With RP-C on the component three
18Silicagel column carries out chromatography, uses methyl alcohol: 70 of water: 30-95: 5 mixture wash-out obtains compound 3,22mg.
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|---|---|---|---|
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|---|---|---|---|
| CNB2007100716524A CN100467473C (en) | 2007-01-17 | 2007-01-17 | New compound prepared by ice city streptomyces and preparation method |
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ID=38888642
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105087710A (en) * | 2014-10-20 | 2015-11-25 | 杭州辰西生物科技有限公司 | Method and fermentation medium for producing milbemycins through streptomyces fermentation |
| CN105087711A (en) * | 2014-10-20 | 2015-11-25 | 杭州辰西生物科技有限公司 | Fermentation medium for producing milbemycins through fermentation of streptomycete and fermentation culture method |
| CN105906650A (en) * | 2016-04-27 | 2016-08-31 | 东北农业大学 | Novel macrolides compounds and preparation methods and application thereof |
| CN105968122A (en) * | 2016-05-12 | 2016-09-28 | 东北农业大学 | 16-membered ring macrolides compound as well as preparation method and application thereof |
| CN106432264A (en) * | 2016-09-06 | 2017-02-22 | 东北农业大学 | Two kinds of macrolide compound and preparation method and application thereof |
| CN106977525A (en) * | 2017-04-19 | 2017-07-25 | 丽珠集团福州福兴医药有限公司 | A kind of meter Bei Er mycins preparation method |
| CN110526925A (en) * | 2019-07-16 | 2019-12-03 | 遵义市第一人民医院 | A kind of separation method of 25 β--23 β of secondary cyclobutenyl-isobutyl acyloxy mibemycin derivative and its application |
| CN111004252A (en) * | 2019-12-11 | 2020-04-14 | 台州职业技术学院 | Sixteen-membered macrolide compound and preparation method and application thereof |
| CN111303184A (en) * | 2019-12-11 | 2020-06-19 | 台州职业技术学院 | Macrolide compound and preparation method and application thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4144352A (en) * | 1977-12-19 | 1979-03-13 | Merck & Co., Inc. | Milbemycin compounds as anthelmintic agents |
-
2007
- 2007-01-17 CN CNB2007100716524A patent/CN100467473C/en not_active Expired - Fee Related
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