CN104844465A - Compound for regulating plant growth and preparation containing same - Google Patents
Compound for regulating plant growth and preparation containing same Download PDFInfo
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- CN104844465A CN104844465A CN201510144785.4A CN201510144785A CN104844465A CN 104844465 A CN104844465 A CN 104844465A CN 201510144785 A CN201510144785 A CN 201510144785A CN 104844465 A CN104844465 A CN 104844465A
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Abstract
The present invention relates to a compound for regulating plant growth and a preparation containing the compound. The structural formula of the compound is shown in the formula I. The compound is produced by reaction of abscisic acid and hexanoic acid diethylamino ethyl ester. The present invention also provides a liquid composition for regulating the growth of plants, which uses the compound represented by the above formula I as active ingredients. The liquid composition also contains antioxidants, ultraviolet absorbers and surfactants. The compound represented by the formula I has a high solubility in water, can be diluted with water at arbitrary proportion and precipitation does not occur; biological activity experiments show that the activity of the compound represented by the formula I is higher than the activity of the equal amount of abscisic acid, which indicates that the presence of the hexanoic acid diethylamino ethyl ester plays a synergistic role on abscisic acid activity. The compound represented by the formula I in the liquid composition has good storage stability and photochemical stability.
Description
Technical field
The invention belongs to agrochemicals technical field, be specifically related to a kind of compound for coordinate plant growth and the preparation containing this compound.
Background technology
Diethylamino ethanol caproate, is plant growth promoter, can improves chlorophyll content of plant, strengthens photosynthesis, promotes cell fission, elongation and plant C N metabolism, has volume increase, precocity, promotes painted, oil recovery enhancement and disease-resistant, degeneration-resistant effect.But it is water-soluble poor, on market, the formulation products of high-content is based on Citrate trianion.
Dormin (ABA) in agriculture production for increasing crop yield, make fruit ripen in advance and promote painted, increase stress resistance of plant, retarding of growing and florescence alternation etc.But dormin dissolves slowly in water, and solubleness is poor, this brings inconvenience just to the packed and transported of preparation and use, is difficult to the preparation making high-content.And the structure of dormin height conjugation easily slow oxidation occurring when storing, being easily isomerizated into the transconfiguration of non-activity in the sun and resolving into other product further, greatly reducing the result of use of dormin.So, the stable dormin preparation of high-content for dormin production and transport and use significant.
Summary of the invention
Technical problem to be solved by this invention is that a kind of solvability in water of exploitation is better than dormin, the new compound that specific activity dormin is high simultaneously, thus the result of use improving medicament, and overcomes the dormin defect that poor solubility inconvenience is packed and used in water.
In order to solve the problems of the technologies described above, the invention provides a kind of compound, its structural formula is such as formula shown in I:
Shown in above-mentioned formula I, compound is prepared by the method comprised the steps: dormin and diethylamino ethanol caproate are reacted, obtain the mixture containing compound shown in formula I.
In aforesaid method, the mol ratio of dormin and diethylamino ethanol caproate is 1:2 ~ 2:1.
The temperature of described reaction is 10 DEG C ~ 70 DEG C, specifically can be 30 DEG C or 55 DEG C.
The time of described reaction is 0.5h ~ 24h, specifically can be 2h or 24h.
Described reaction is carried out in organic solvent.
Described organic solvent can be selected from following at least one: acetone, ethyl acetate, methyl alcohol, ethanol, acetonitrile, toluene or dimethylbenzene.
Described organic solvent specifically can be ethyl acetate or ethanol.
Aforesaid method also comprises and is separated containing the mixture of compound shown in formula I the step obtaining compound shown in formula I from described.Concrete operations are as follows: by described containing the removal of solvents in the mixture of compound shown in formula I, obtain the mixture of compound shown in formula I and unreacted raw material; By described mixture by column chromatography purification, obtain compound shown in formula I.
Described column chromatography is: with volume ratio be the ethyl acetate of 1:10 ~ 10:1 and sherwood oil mixed solution for elutriant (as the ethyl acetate of 1:4 and the mixed solution of sherwood oil) for eluent carries out wash-out, collect the elution fraction containing target product, and the solvent that removing is wherein contained, obtain compound shown in described formula I.
Compound shown in above-mentioned formula I also belongs to protection scope of the present invention preparing the application in plant-growth regulator.
Present invention also offers more than one and state the liquid preparation composition for coordinate plant growth that compound shown in formula I is activeconstituents, to overcome easy slow oxidation when it stores, during use, hold degradation-labile defect in the sun.
In described liquid preparation composition, the mass percentage of compound shown in formula I is 0.01% ~ 99%, is preferably 20%-80%, specifically can be 20%, 50% or 80%.
Described liquid preparation composition can by compound shown in formula I, antioxidant, uv-absorbing agent, tensio-active agent and solvent composition, wherein, the content of compound shown in described formula I is 0.01% ~ 99%, oxidation preventive content is 0.1% ~ 5%, uv-absorbing agent content is 0.1% ~ 30%, surfactant content is 0.1% ~ 20%, solvent is surplus.
Preferably, in described liquid preparation composition, the content of compound shown in described formula I is 20% ~ 80%, oxidation preventive content is 0.1% ~ 5%, uv-absorbing agent content is 0.1% ~ 5%, surfactant content is 1% ~ 5%, solvent is surplus.
Described antioxidant can be at least one in tertiary butylated hydroquinone, Tenox PG, ethoxyquin woods, butylated hydroxytoluene and butyl hydroxyanisole, specifically can be tertiary butylated hydroquinone or Tenox PG.
Described uv-absorbing agent can be at least one in BP-4 sodium and ESCALOL 567.
Described tensio-active agent can be at least one in diisobutyl sodium naphthalene sulfonate, sodium lauryl sulphate, fatty alcohol-polyoxyethylene ether, alkylphenol polyoxyethylene, naphthalenesulfonate formaldehyde condensation compound, nonyl phenol formaldehyde condensation products polyethenoxy ether sulphonate and maleic acid di-sec-octyl sulfonate, specifically can be penetrating agent JFC or fast T.
Described solvent can be at least one in propylene glycol and Macrogol 200, poly(oxyethylene glycol) 400, Polyethylene Glycol-600, specifically can be propylene glycol or poly(oxyethylene glycol) 400.
Above-mentioned liquid preparation composition is prepared by following method: compound shown in the formula I taking described content, add the tensio-active agent of described content, join in the solvent of described content, abundant stirring and dissolving, add the antioxidant of described content, add the uv-absorbing agent of described content after dissolving, solvent supplies 100%, compound liquid preparation composition shown in the formula I that namely abundant stirring and dissolving obtains described content.
Dormin and diethylamino ethanol caproate are carried out reaction and have obtained compound shown in formula I by the present invention, the solubleness of compound shown in described formula I in water is high, Precipitation can be there is not arbitrarily than being watered dilution, biological activity test shows, the activity of compound shown in formula I is higher than the activity of dormin waiting amount of substance, and this shows that the activity of the existence of ethylaminoethyl alcohol ester to dormin plays synergistic function.Add in the liquid preparation composition made for activeconstituents with compound shown in formula I storage that antioxidant and uv-absorbing agent can significantly improve compound shown in formula I be watered dilution with it after photochemical stability in application, thus ensure the result of use of compound shown in formula I.
Accompanying drawing explanation
Fig. 1 is the high-efficient liquid phase chromatogram of dormin ABA.
Embodiment
Below by specific embodiment, the present invention will be described, but the present invention is not limited thereto.
The experimental technique used in following embodiment if no special instructions, is ordinary method; Reagent used in following embodiment, material etc., if no special instructions, all can obtain from commercial channels.
The test plant used in following embodiment is wheat, and kind is Jimai 22, the seed selection of crop investigations institute of academy of agricultural sciences of Shandong Province, and authorization is numbered Lu Nong and examines 2006050, and the public can buy from market.
The reagent agent used in following embodiment:
Dormin standard substance (purity >98%) are purchased from lark prestige company, and the former medicine of dormin (purity 91.8%), purchased from Sichuan Guoguang Agrochemical Co., Ltd..
Diethylamino ethanol caproate (purity 98%), purchased from Zheng Shi Chemical Co., Ltd..
Solvent propylene glycol is purchased from traditional Chinese medicines chemical reagent company limited.
Solvent poly(oxyethylene glycol) 400 is purchased from traditional Chinese medicines chemical reagent Beijing company.
Antioxidant tertiary butyl quinhydrones is purchased from traditional Chinese medicines chemical reagent Beijing company.
Antioxidant Tenox PG is purchased from traditional Chinese medicines chemical reagent company limited.
Antioxidant butyl hydroxyanisole is purchased from traditional Chinese medicines chemical reagent company limited.
Uv-absorbing agent BP-4 sodium is purchased from lark prestige Science and Technology Ltd..
Uv-absorbing agent ESCALOL 567 is purchased from lark prestige Science and Technology Ltd..
Surfactant penetrant JFC is purchased from auxiliary reagent factory of Xingtai city.
The fast T of tensio-active agent is purchased from Shanghai Jinshan Chemical Co., Ltd..
Shown in the liquid preparation Chinese style I of preparation in embodiment 3 ~ 5 in following embodiment, the storage stability detection method of compound is as follows:
Heat storage stability carries out according to GB/T 19136-2003 method, and regular storage stability is in room temperature and the degraded situation (in structure, ABA part is index) measuring compound shown in formula I after 6 months.
Shown in the liquid preparation Chinese style I of preparation in embodiment 3 ~ 5 in following embodiment, the photochemical stability detection method of compound is as follows:
Under the low light level, volumetric molar concentration liquid preparation being watered compound shown in dilution accepted way of doing sth I is the diluent of 1135 μm of ol/L, divide and be filled to (specification is 16mm × 13mm × 150mm) in 2 brace plug quartz test tubes, often prop up test tube packing 10ml, to wherein wrap up, as dark control by a test tube masking foil.Compound distilled water solution shown in another preparation formula I (volumetric molar concentration of compound shown in formula I is 1135 μm of ol/L), divides and is filled in two brace plug quartz test tubes, often prop up packing 10ml, will wherein wrap up, as dark control by a test tube masking foil.Enter to embed in the circular channels of XPA-7 type photochemical reaction instrument by above-mentioned 4 test tubes, tank temperature is controlled at 22 DEG C by constant thermal apparatus at low temperature.It is 400r/min that liquid in test tube controls agitation speed by magneton, all test tubes rotate around quartzy cold-trap with 5r/min speed, 300w high voltage mercury lamp is inserted in cold-trap, uv filter is around being inserted in around cold-trap to obtain superpower UV-light, outside light shield keeps shielding status, until light stability.Once, sampling amount is 0.5ml, and the sample obtained puts into ice bath rapidly in sampling in a hour.Utilize compounds content shown in liquid chromatographic detection formula I (with ABA part in structure for index).Ultraviolet ray intensity in test tube place ultraviolet ray intensity and summer noon sun is in table 1
UV intensity in the ultraviolet ray intensity that in table 1 photochemical reaction instrument, test tube accepts and summer noon sun
The detection method of compounds content shown in formula I following (with ABA content for Testing index):
The high performance liquid chromatograph (Agilent company of the U.S., 1200) with UV-detector is used to carry out.Chromatographic column is Agilent Eclipse Plus C18 column (4.6mm × 5 μm, 250mm), column temperature controls at 30 DEG C, and moving phase is 60% (v/v) methanol aqueous solution containing 0.2% (v/v) acetic acid, and flow velocity is 1.0ml/min.(under this chromatographic condition, compound decomposition shown in formula I has become dormin, thus by dormin content reflection formula I shown in the content of compound) content of dormin measured at 260nm place by external standard method.The retention time of dormin is 5.0min (as shown in Figure 1).
Take dormin as external standard, production standard curve, with the peak area of dormin for X-coordinate, the concentration (mg/L) of dormin is ordinate zou drawing standard curve, and the linear equation obtaining dormin is y=0.0112x-3.6718, R
2=0.9985.Related assays data are in table 2.
The linear relationship measurement result of table 2 dormin
| The concentration (mg/L) of compound shown in formula I | 356 | 71.2 | 14.24 | 2.848 | 0.5696 |
| The area of compound shown in formula I | 31864.4 | 7602.5 | 1491.6 | 295.5 | 57.5 |
The preparation of compound shown in embodiment 1, formula I
In 100ml round-bottomed flask, add 5.75g 91.8% dormin (0.02mol), 4.39g 98% diethylamino ethanol caproate (0.02mol), 10ml ethyl acetate, be heated to 55 DEG C and insulated and stirred 24 hours; After completion of the reaction, underpressure distillation goes out solvent, it (take volume ratio as the ethyl acetate of 1:4 and sherwood oil mixed solution for elutriant carries out wash-out that the mixture obtained carries out column chromatography, according to thin-layer chromatography, collect the elution fraction containing target product), underpressure distillation is taken off solvent and is obtained homogeneous orange-yellow thick transparent liquid 8.15g again, and be compound shown in formula I, productive rate is 85%.
Structural identification data are as follows:
Nuclear magnetic data: δ (300MHz, CDCl
3): 0.86 ~ 0.91 (m, 3H), 1.00 (s, 3H), 1.09 (s, 3H), 1.17 (t, 6H, J=7.19Hz), 1.23 ~ 1.33 (m, 7H), 1.56 ~ 1.66 (m, 2H), 1.91 ~ 1.94 (dd, 6H, J
1=1.33, J
2=10.38), 2.05 (s, 3H), 2.23 ~ 2.34 (m, 3H), 2.51 (s, 1H), 2.84 ~ 2.91 (dd, 4H, J
1=7.22, J
2=14.4), 3.01 (t, 2H, J=5.84), 4.08 ~ 4.16 (dd, 2H, J
1=7.13, J
2=14.27), 4.32 (t, 2H, J=5.82), 5.80 (s, 1H), 5.89 (s, 1H), 6.05 (s, 1H).
The preparation of compound shown in embodiment 2, formula I
In 100ml round-bottomed flask, add 11.5g 91.8% dormin (0.04mol), 8.78g 98% diethylamino ethanol caproate (0.04mol), 20ml ethanol, be heated to 30 DEG C and insulated and stirred 2 hours; After completion of the reaction, underpressure distillation goes out solvent, it (take volume ratio as the ethyl acetate of 1:4 and sherwood oil mixed solution for elutriant carries out wash-out that the mixture obtained carries out column chromatography, according to thin-layer chromatography, collect the elution fraction containing target product), underpressure distillation is taken off solvent and is obtained homogeneous orange-yellow thick transparent liquid 15.34g again, and must be compound shown in formula I, productive rate be 80%.
Confirm consistent with compound prepared by embodiment 1 through nuclear-magnetism.
The mass content of compound shown in embodiment 3, formula I is the preparation of the liquid preparation composition of 20%
Take compound 20g shown in the formula I for preparing according to embodiment 1 method, penetrating agent JFC 2g, add in 50ml propylene glycol, abundant stirring and dissolving, add 0.1g tertiary butylated hydroquinone, add 2g BP-4 sodium after dissolving, supply 100g with propylene glycol, the mass content that namely abundant stirring and dissolving obtains compound shown in formula I is the liquid preparation composition of 20%.
The mass content of compound shown in embodiment 4, formula I is the preparation of the liquid preparation composition of 50%
Take compound 50g shown in the formula I for preparing according to embodiment 1 method, fast T 3g, add in 30ml propylene glycol, abundant stirring and dissolving, add 0.1g Tenox PG, add 2g ESCALOL 567 after dissolving, 100g supplied by propylene glycol, and the mass content that namely abundant stirring and dissolving obtains compound shown in formula I is the liquid preparation composition of 50%.
The mass content of compound shown in embodiment 5, formula I is the preparation of the liquid preparation composition of 80%
Take compound 80g shown in the formula I for preparing according to embodiment 1 method, fast T 3g, add in 10ml poly(oxyethylene glycol) 400, abundant stirring and dissolving, add 0.2g butyl hydroxyanisole, add 4g BP-4 sodium after dissolving, supply 100g by poly(oxyethylene glycol) 400, the mass content that namely abundant stirring and dissolving obtains compound shown in formula I is the liquid preparation composition of 80%.
The evaluated biological activity of compound shown in embodiment 6, formula I
Choose Jimai 22 seed of the same size, respectively compound, diethylamino ethanol caproate and dormin shown in the formula I of 300 μm of ol/L containing a small amount of tween 20 are joined (built-in double-layer filter paper) in the batch cultur ware of diameter 90mm, every ware adds 4ml, and each process arranges 5 repetitions.The wheat seed after 25 sterilizations is sown in every ware.With clear water process in contrast.In growth cabinet, carrying out dark germination test, add up the sprouting situation of every day, breaking through seed coat for sprouting with radicle or plumule.
Shown in table 3 formula I, compound is on the impact of wheat germination
Result shows: under equivalent molar concentration, compound shown in formula I restrained effectively the sprouting of wheat seed, and at the germination rate of the 3rd day significantly lower than the acid-treated germination rate that comes off, and diethylamino ethanol caproate contrast with clear water compared with do not suppress the sprouting of seed, compound shown in formula I has obvious synergism, and its effect is better than dormin.
The storage stability of compound shown in the liquid composition Chinese style I of embodiment 7, embodiment 3 ~ 5 preparation
The storage stability of compound liquor shown in table 4 formula I (with ABA part in structure for index, not add the corresponding preparation of uv-absorbing agent and antioxidant in contrast, all values is all scaled the per-cent of relative initial content)
Result shows, accelerate storage after two weeks to impinging upon high temperature, compounds content declines about 1% ~ 4%, and normal temperature storage declines about 5% ~ 15% after half a year; And all there is not oxidative degradation in the compound added in the embodiment 3 ~ 5 of antioxidant.Show that antioxidant maintains the stability of compound effectively.
The photochemical stability of compound shown in the liquid composition Chinese style I of embodiment 8, embodiment 3 ~ 5 preparation
The photochemical stability (contrast is the distilled water solution of compound shown in 1135 μm of ol/l formula I, and so that in structure, ABA part is for index, all values is all scaled the per-cent of relative initial content) of compound liquid preparation shown in table 5 formula I
Result shows: to impinge upon irradiate 1 hour under superpower ultraviolet after drop to 57%, and in embodiment 3 ~ 5, light stability promotes about 5 ~ 10%.Irradiate after 8 hours, contrast remains 25%, and embodiment 3 ~ 5 still remains 27% ~ 29%.What show uv-absorbing agent adds the light stability significantly improving compound shown in formula I.
Claims (8)
1. compound shown in formula I:
2. prepare a method for compound shown in claim 1 Chinese style I, comprise the steps: dormin and diethylamino ethanol caproate to react, to obtain final product.
3. method according to claim 2, is characterized in that: the mol ratio of described dormin and described diethylamino ethanol caproate is 1:2 ~ 2:1;
The temperature of described reaction is 10 DEG C ~ 70 DEG C;
The time of described reaction is 0.5h ~ 24h.
4. compound shown in claim 1 Chinese style I is preparing the application in plant-growth regulator.
5. a liquid preparation composition, is characterized in that: described liquid preparation composition with compound shown in formula I according to claim 1 for activeconstituents;
In described liquid preparation composition, the mass percentage of compound shown in described formula I is 0.01% ~ 99%.
6. liquid preparation composition according to claim 5, is characterized in that: described liquid preparation composition is by compound shown in formula I, antioxidant, uv-absorbing agent, tensio-active agent and solvent composition;
Wherein, the content of compound shown in described formula I is 0.01% ~ 99%, oxidation preventive content is 0.1% ~ 5%, uv-absorbing agent content is 0.1% ~ 30%, surfactant content is 0.1% ~ 20%, solvent is surplus.
7. liquid preparation composition according to claim 6, is characterized in that: described solvent is at least one in propylene glycol and polyoxyethylene glycol;
Described antioxidant is at least one in tertiary butylated hydroquinone, ethoxyquin woods, butylated hydroxytoluene, butyl hydroxyanisole and Tenox PG;
Described uv-absorbing agent is at least one in BP-4 sodium and ESCALOL 567;
Described tensio-active agent is at least one in diisobutyl sodium naphthalene sulfonate, sodium lauryl sulphate, fatty alcohol-polyoxyethylene ether, alkylphenol polyoxyethylene, naphthalenesulfonate formaldehyde condensation compound, nonyl phenol formaldehyde condensation products polyethenoxy ether sulphonate and maleic acid di-sec-octyl sulfonate.
8. the liquid preparation composition according to any one of claim 5-7 is as the application of plant-growth regulator in agriculture production.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101423443A (en) * | 2008-11-21 | 2009-05-06 | 深圳市朗钛生物科技有限公司 | Water soluble effervescence composition and method of making the same |
| CN101475420A (en) * | 2009-01-23 | 2009-07-08 | 深圳市朗钛生物科技有限公司 | Fertilizer water-dispersion granule and preparation thereof |
| CN104388375A (en) * | 2014-10-31 | 2015-03-04 | 四川省兰月科技有限公司 | Microbial growth promoter and preparation method thereof |
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2015
- 2015-03-30 CN CN201510144785.4A patent/CN104844465B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101423443A (en) * | 2008-11-21 | 2009-05-06 | 深圳市朗钛生物科技有限公司 | Water soluble effervescence composition and method of making the same |
| CN101475420A (en) * | 2009-01-23 | 2009-07-08 | 深圳市朗钛生物科技有限公司 | Fertilizer water-dispersion granule and preparation thereof |
| CN104388375A (en) * | 2014-10-31 | 2015-03-04 | 四川省兰月科技有限公司 | Microbial growth promoter and preparation method thereof |
Non-Patent Citations (2)
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| 张柏莲: "8%胺鲜酯水剂在白菜上应用药效试验", 《福建稻麦科技》 * |
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