CN113229286A - Bactericidal composition containing neobynine derivatives and anthraquinone derivatives - Google Patents
Bactericidal composition containing neobynine derivatives and anthraquinone derivatives Download PDFInfo
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- CN113229286A CN113229286A CN202110561427.9A CN202110561427A CN113229286A CN 113229286 A CN113229286 A CN 113229286A CN 202110561427 A CN202110561427 A CN 202110561427A CN 113229286 A CN113229286 A CN 113229286A
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- derivative
- neobynine
- rhubarb
- anthraquinone
- emodin
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- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 30
- 239000000203 mixture Substances 0.000 title claims abstract description 26
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 150000004056 anthraquinones Chemical class 0.000 title claims abstract description 19
- LQGUBLBATBMXHT-UHFFFAOYSA-N chrysophanol Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC(O)=C3C(=O)C2=C1O LQGUBLBATBMXHT-UHFFFAOYSA-N 0.000 claims abstract description 20
- FFWOKTFYGVYKIR-UHFFFAOYSA-N physcion Chemical compound C1=C(C)C=C2C(=O)C3=CC(OC)=CC(O)=C3C(=O)C2=C1O FFWOKTFYGVYKIR-UHFFFAOYSA-N 0.000 claims abstract description 20
- PKUBGLYEOAJPEG-UHFFFAOYSA-N physcion Natural products C1=C(C)C=C2C(=O)C3=CC(C)=CC(O)=C3C(=O)C2=C1O PKUBGLYEOAJPEG-UHFFFAOYSA-N 0.000 claims abstract description 20
- YDQWDHRMZQUTBA-UHFFFAOYSA-N Aloe emodin Chemical compound C1=CC=C2C(=O)C3=CC(CO)=CC(O)=C3C(=O)C2=C1O YDQWDHRMZQUTBA-UHFFFAOYSA-N 0.000 claims abstract description 14
- 201000010099 disease Diseases 0.000 claims abstract description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 14
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- 239000010282 Emodin Substances 0.000 claims abstract description 10
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- NTGIIKCGBNGQAR-UHFFFAOYSA-N Rheoemodin Natural products C1=C(O)C=C2C(=O)C3=CC(O)=CC(O)=C3C(=O)C2=C1O NTGIIKCGBNGQAR-UHFFFAOYSA-N 0.000 claims abstract description 10
- WLXGUTUUWXVZNM-UHFFFAOYSA-N anthraglycoside A Natural products C1=C(C)C=C2C(=O)C3=CC(OC)=CC(O)=C3C(=O)C2=C1OC1OC(CO)C(O)C(O)C1O WLXGUTUUWXVZNM-UHFFFAOYSA-N 0.000 claims abstract description 10
- NZPQWZZXRKZCDU-UHFFFAOYSA-N chrysophanol Natural products Cc1cc(O)c2C(=O)c3c(O)cccc3Oc2c1 NZPQWZZXRKZCDU-UHFFFAOYSA-N 0.000 claims abstract description 10
- RHMXXJGYXNZAPX-UHFFFAOYSA-N emodin Chemical compound C1=C(O)C=C2C(=O)C3=CC(C)=CC(O)=C3C(=O)C2=C1O RHMXXJGYXNZAPX-UHFFFAOYSA-N 0.000 claims abstract description 10
- VASFLQKDXBAWEL-UHFFFAOYSA-N emodin Natural products OC1=C(OC2=C(C=CC(=C2C1=O)O)O)C1=CC=C(C=C1)O VASFLQKDXBAWEL-UHFFFAOYSA-N 0.000 claims abstract description 10
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- INYYVPJSBIVGPH-QHRIQVFBSA-N Sinomenine Chemical class C([C@@H]1N(CC2)C)C3=CC=C(OC)C(O)=C3[C@@]32[C@@H]1C=C(OC)C(=O)C3 INYYVPJSBIVGPH-QHRIQVFBSA-N 0.000 claims description 6
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- 241001344131 Magnaporthe grisea Species 0.000 abstract description 2
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- -1 anthraquinone compounds Chemical class 0.000 description 9
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PZIIKMBOSNKNFZ-UHFFFAOYSA-N 5-methylindolo[2,3-b]quinoline Chemical compound C1=CC=C2N(C)C3=NC4=CC=CC=C4C3=CC2=C1 PZIIKMBOSNKNFZ-UHFFFAOYSA-N 0.000 description 2
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- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 238000010009 beating Methods 0.000 description 1
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
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- KURWKDDWCJELSV-UHFFFAOYSA-N cryptolepine Chemical class N1=C2C=CC=C[C]2C(N2C)=C1C=C1[C]2C=CC=C1 KURWKDDWCJELSV-UHFFFAOYSA-N 0.000 description 1
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- 230000000642 iatrogenic effect Effects 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
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- 238000011081 inoculation Methods 0.000 description 1
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- KAQKFAOMNZTLHT-OZUDYXHBSA-N prostaglandin I2 Chemical compound O1\C(=C/CCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 KAQKFAOMNZTLHT-OZUDYXHBSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
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- MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 description 1
- 229960003165 vancomycin Drugs 0.000 description 1
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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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- 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
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
Abstract
The invention belongs to the field of agricultural bactericide compounding, and discloses a composition containing a neobynine derivative Z-24 and anthraquinone components (emodin, physcion, chrysophanol and aloe-emodin) in rheum officinale and a mixing concentration thereof. The composition is applied to preventing and treating plant diseases caused by rhizoctonia solani, sclerotinia sclerotiorum, fusarium graminearum, botrytis cinerea, magnaporthe grisea and phytophthora capsici, and the mass percentages of the neobylonine derivative Z-24 and the anthraquinone components are 1:500, 1:100, 1:50 and 1: 25. The bactericidal composition disclosed by the invention has the advantages of wider bactericidal spectrum, lower toxicity, capability of effectively delaying the generation of drug resistance of plant pathogenic bacteria and the like, and has further research and development values.
Description
Technical Field
The invention relates to the field of agricultural bactericides, which comprises an active component A: a neobystander derivative, an active component B: anthraquinone compounds emodin, aloe-emodin, physcion and chrysophanol in traditional Chinese medicine rhubarb are effective components, and the composition is used for preventing and treating diseases caused by plant pathogenic fungi such as rhizoctonia solani, sclerotinia sclerotiorum, botrytis cinerea, fusarium graminearum, rice blast, phytophthora capsici and the like.
Background
China is a big country for crop production, but crop diseases are frequently repeated, more than 1600 pests appear all the year round, nearly 100 pests which cause serious harm to crops, such as wheat scab, rice blast, potato late blight and other major crop disease development situations seriously threaten grain stable development. Wherein 70-80% of crop diseases are caused by plant pathogenic fungi, and more than 100 million people lose lives because of the pandemic of late blight of potato in Ireland in 1845-1852 years; in 1943, the pandemic of Bengal rice flaccid leaf caused about 200 ten thousand people to be starved. Even if science and technology develops to the present, the loss of the plant diseases to agriculture still feels eye surprise. The invasion of harmful species and the increase of the spreading speed thereof lead the damage degree of plant diseases to be increasingly intensified. The use of chemical reagents has been the main means for controlling plant fungal diseases, but the prohibition of highly toxic pesticides in various regions of the world and the continuous development of the drug resistance of various plant pathogenic fungi lead researchers to continuously raise the attention of the agricultural bactericidal composition with small toxic and side effects, safety and good environmental compatibility. The compounding of bactericides with different action mechanisms has the advantages of reducing the dosage of chemical bactericides, expanding the bactericidal spectrum, reducing the toxicity, reducing the occurrence of drug resistance and the like, thereby becoming an important means for solving plant diseases.
Neographolide (Neocryptolepine) (5-methyl-5H-indole [2, 3-b ] -quinoline) is a cryptolepine isomer, a bearing quaternary heterocyclic ring linearly fuses an indole ring and a quinoline ring, is a natural alkaloid separated from a climbing plant of African white vine (Cryptolepis sinensis (Lour.) Merr.), is an African traditional medicine, has various biological activities including antitumor, antibacterial, antifungal and antiparasitic activities, has various activities and higher content in plants, and becomes a natural source lead structure widely modified and optimized by pharmaceutical chemists at present.
Rhubarb (Rheum palmatum L.) has a long medicinal history, is one of the famous special medicinal materials in China, and is a typical representative of traditional Chinese medicinal materials in multi-effect, multi-variety and multi-property areas. As a bulk medicinal material and a genuine medicinal material in Gansu province, anthraquinone compounds contained in the medicinal material are main research objects, and modern pharmacological research shows that rhubarb has various pharmacological activities such as antifungal activity, antitumor activity, antioxidant activity and the like. For example, anthraquinone derivatives are useful against methicillin-resistant staphylococcus aureus (MIC 4 μ g/mL, rhein), vancomycin-resistant enterococci (MIC 2-8 μ g/mL, cationic anthraquinone derivatives), escherichia coli (MIC 16 μ g/mL, emodin), candida albicans (MIC 50 μ g/mL, rhubarb extract), botrytis cinerea (EC ═ 50 μ g/mL, rheum officinale extract), and the like50Rhein 8.28. mu.g/mL), Blumeria buchneri (EC)504.7 mug/mL chrysophanol, EC500.48 mug/mL, physcion) and the like have strong inhibitory activity, wherein the research on the antibacterial activity of the drug-resistant staphylococcus aureus is the most extensive; in addition, it also has growth inhibiting or killing effect on bollworm, blood-twirling thatch nematode, etc. However, the research on rhubarb anthraquinone compounds is mainly focused on iatrogenic pathogenic bacteria, and the related research on plant pathogenic bacteria is less. According to the existing research, the natural anthraquinone derivative contained in the rhubarb has a narrow antibacterial spectrum on plant pathogenic fungi, has general antibacterial activity on most of the plant pathogenic fungi, and has a solubility problem at high concentration. Based on the research, the neohederin derivative Z-24 is used as a main agent, anthraquinone components in rhubarb are used as auxiliary agents, and the synergistic interaction research is carried out on common plant pathogenic fungi such as rhizoctonia solani, sclerotinia sclerotiorum, botrytis cinerea, fusarium graminearum, rice blast, phytophthora capsici and the like, so that the antibacterial activity of the neohederin derivative Z-24 is improved, and the dosage and the toxicity of the neohederin derivative Z-24 are reduced.
Disclosure of Invention
The invention aims to provide a bactericide composition containing a neobylonine derivative and anthraquinone compounds, which is used for preventing and treating plant diseases caused by rhizoctonia solani, sclerotinia sclerotiorum, botrytis cinerea, fusarium graminearum, rice blast, phytophthora capsici and the like.
In order to achieve the purpose, the technical scheme of the invention is as follows:
a bactericide composition containing a neocelandine derivative and an anthraquinone compound comprises an active component A and an active component B, wherein the active component A is a neocelandine derivative Z-24, and the active component B is an anthraquinone compound: emodin, aloe-emodin, physcion, and chrysophanol.
The bactericide composition provided by the invention has the following advantages as an agricultural bactericide:
1) the bactericidal composition provided by the invention can reduce the dosage of the main ingredient neobynine derivative Z-24 and reduce the pesticide cost.
2) The bactericidal composition provided by the invention improves the control effect of the natural anthraquinone compounds with rich sources on plant pathogenic bacteria, and has an obvious synergistic effect with Z-24 at a certain compounding ratio.
3) The bactericidal composition provided by the invention has different action mechanisms of the effective components, can effectively delay and reduce the generation of drug resistance of phytopathogen, and enhances the control effect.
Detailed Description
In order to better understand the essence of the present invention, the following detailed description is further illustrated, but the present invention is not limited to these examples. In these examples, all percentages are by weight unless otherwise indicated.
Example 1: a bactericide composition containing Sinomenine derivative Z-24 and anthraquinone compounds comprises active component A and active component B (shown in figure 1), wherein the active component A is Sinomenine derivative Z-24, and the active component B is anthraquinone component in radix et rhizoma Rhei, emodin, physcion, chrysophanol, and aloe emodin.
Example 2: indoor bacteriostatic activity determination of plant pathogenic fungi
The plant pathogenic fungi used in the experiment are strains stored at 4 ℃ in a laboratory, and all culture media used by the plant pathogenic fungi in the laboratory are potato agar glucose culture media (PDA for short). The PDA culture medium formula comprises: 200g of potato (peeled), 20g of glucose, 15g of agar and 1000mL of distilled water. And (4) determining the antibacterial activity by adopting a hypha growth rate method.
The preparation method of the PDA culture medium comprises the following steps: cleaning and peeling potato, weighing 200g, cutting into small pieces, adding water, boiling (boiling for 20-30 min, and being capable of being punctured by a glass rod), filtering with four layers of gauze, adding distilled water into a beaker to 1000mL, adding 15-20g of agar according to experimental requirements, adding 20g of glucose, stirring to fully dissolve, subpackaging in a conical flask, and sterilizing at 121 ℃ for 20 min for later use.
Experimental methods
1) Hypha growth rate method.
1. Firstly, plant pathogenic bacteria are cultured on a PDA flat plate at 25 ℃ for 3-6 days for activation.
2. Heating PDA culture medium to melt, cooling to 45-50 deg.C, adding the sterilizing compositions with different concentrations, and making into tablet with medicine.
3. According to the aseptic operation procedure, a hole puncher is used for beating a circular fungus cake (the diameter is 5mm) at the edge of each bacterial strain hypha cultured for 3-6 days (the growth conditions are consistent as much as possible), then a inoculation needle is used for picking the circular fungus cake to the center of a medicine-containing flat plate, and then a culture dish is placed in an incubator (25 ℃) for culture.
4. After the blank control group is full, the Growth condition of the hyphae is observed and measured, the diameter is measured by adopting a cross method, the data is processed, and the hyphae Growth Inhibition rate (PGI) is calculated.
5. Hypha growth inhibition (%) was (control hypha diameter-treated hypha diameter)/(control hypha diameter-cake diameter) × 100
6. Each treatment was repeated 3 times.
Example 3: indoor activity determination of 6 plant germs by mixing neobyssurine derivative Z-24 and active component B
The compounding synergy of the bactericide is calculated according to Abbott (1925) formula, and the synergistic coefficient of the mixed different medicaments is calculated as follows:
PGI1 and PGI2 in the formula respectively represent Z-24(1), the inhibition rate of single dose of anthraquinone component (2) in rhubarb on the growth of hyphae, OPGI and EPGI respectively represent the inhibition rate of actually observed mixed dose on the growth of hyphae and the inhibition rate of theoretical mixed dose on the growth of hyphae. AI is Abbott index, and AI is more than or equal to 1.5 for synergistic effect; AI <0.5 is antagonistic; an AI between 0.5 and 1.5 indicates an additive effect.
TABLE 1 indoor toxicity synergism of Z-24 and active component B blending on Magnaporthe grisea
As can be seen from Table 1, when the mixing mass ratio of Z-24 to active component B is 1:25, the synergistic effect on rice blast fungi is obvious, and the measured values of the growth inhibition rate of the mixed agent on the hypha of rice blast fungi are all about 90%.
TABLE 2 indoor toxicity synergistic Effect of Z-24 and active component B blending on Fusarium graminearum
As can be seen from Table 2, when the mixing mass ratio of Z-24 to the active component B is 1:25, 1:50 and 1:100, the compound has obvious synergistic effect on fusarium graminearum. When the mass ratio is 1:25 and 1:50, the synergy of Z-24 and physcion is most obvious, and the AI values are 5.32 and 10.36 respectively.
TABLE 3 indoor toxicity synergism of Z-24 and active component B blending on Botrytis cinerea
As can be seen from Table 3, the blending mass ratio of Z-24 to emodin and chrysophanol in the active component B is 1:500, and the blending mass ratio of Z-24 to emodin and chrysophanol in the active component B is 1:2500, so that the synergistic effect on the botrytis cinerea is obvious, and the AI values are 2.03, 3.11, 2.81 and 6.72 respectively.
TABLE 4 indoor toxicity synergism of Z-24 and active ingredient B blending of Ralstonia solanacearum
As can be seen from Table 4, Z-24 and active ingredient B are additive at the given ratio, and have no synergistic effect.
TABLE 5 indoor virulence potentiation of Sclerotinia sclerotiorum by Z-24 and active component B compounding
As can be seen from Table 5, Z-24 and active ingredient B are basically additive at the given ratio, and only Z-24 and chrysophanol show synergistic effect on Sclerotinia sclerotiorum at a ratio of 1: 100.
TABLE 6 indoor toxicity synergism of Z-24 and active component B compounding on Phytophthora capsici
As can be seen from Table 6, Z-24 and active ingredient B are both additive or antagonistic at the stated ratios, with no synergistic effect.
In conclusion, the Z-24 and anthraquinone components in the rhubarb have obvious synergistic effect on part of plant pathogenic bacteria such as botrytis cinerea, fusarium graminearum and rice blast bacteria in a proper proportion, but the synergistic effect on rhizoctonia solani, sclerotinia sclerotiorum and phytophthora capsici is not shown. Wherein, the most obvious Z-24 and physcion composition with synergy has an AI value of 10.36 to fusarium graminearum at a ratio of 1:50, and the actual observation values of the Z-24, the emodin, physcion and aloe-emodin on the inhibition rate of the growth of the hypha of rice blast fungus at a ratio of 1:25 are all about 90%.
The bactericidal composition containing the Sinomenine derivative Z-24, the emodin, the physcion, the aloe-emodin and the chrysophanol can obviously reduce the dosage of the Sinomenine derivative Z-24 and improve the antibacterial activity of anthraquinone compounds. Based on the above, the bactericidal composition provided by the invention has further research and development values.
Claims (8)
1. A sterilization composition containing neobynine derivatives Z-24 and rhubarb anthraquinone components is characterized in that: the effective components include Sinomenine derivative Z-24 and 4 kinds of anthraquinone components (emodin, physcion, aloe-emodin, and chrysophanol) at a weight ratio of 1:500, 1:100, 1:50, and 1: 25.
2. The germicidal composition of claim 1, having the following molecular structural features or names:
component A
Component B
3. The use of the fungicidal composition according to claim 1, which contains the neobynine derivative Z-24 and anthraquinones derived from rhubarb as active ingredients, for controlling diseases caused by Pyricularia oryzae.
4. The use of the bactericidal composition containing the neobynine derivative Z-24 and the anthraquinone components of rheum officinale according to claim 1 for preventing and treating diseases caused by fusarium graminearum.
5. The use of the bactericidal composition containing the Sinomenine derivative Z-24 and the anthraquinone components of rhubarb according to claim 1 for preventing and treating diseases caused by Botrytis cinerea.
6. The use of the fungicidal composition according to claim 1, which contains the neobynine derivative Z-24 and anthraquinones from rhubarb as active ingredients, for the control of diseases caused by rhizoctonia solani.
7. The use of the fungicidal composition according to claim 1, which contains the neobynine derivative Z-24 and anthraquinones from rhubarb, for the prevention and treatment of diseases caused by sclerotinia sclerotiorum.
8. The use of the fungicidal composition according to claim 1, which contains the neobytechin derivative Z-24 and anthraquinones from the group consisting of phytophthora capsici.
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Cited By (2)
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|---|---|---|---|---|
| CN113785848A (en) * | 2021-10-12 | 2021-12-14 | 贵州省烟草公司毕节市公司 | Plant source nematocide and preparation method thereof |
| CN114794159A (en) * | 2022-06-06 | 2022-07-29 | 湖南省林业科学院 | Composition containing camellia saponin as main component for preventing and treating Chinese rose diseases and preparation method thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113785848A (en) * | 2021-10-12 | 2021-12-14 | 贵州省烟草公司毕节市公司 | Plant source nematocide and preparation method thereof |
| CN114794159A (en) * | 2022-06-06 | 2022-07-29 | 湖南省林业科学院 | Composition containing camellia saponin as main component for preventing and treating Chinese rose diseases and preparation method thereof |
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