WO2002091825A2 - Method to protect plants from oomycete pathogens with serratia marcescens - Google Patents
Method to protect plants from oomycete pathogens with serratia marcescens Download PDFInfo
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- WO2002091825A2 WO2002091825A2 PCT/US2002/015195 US0215195W WO02091825A2 WO 2002091825 A2 WO2002091825 A2 WO 2002091825A2 US 0215195 W US0215195 W US 0215195W WO 02091825 A2 WO02091825 A2 WO 02091825A2
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- serratamolide
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
-
- 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
- A01N63/00—Biocides, pest repellants or attractants, or plant growth regulators containing microorganisms, viruses, microbial fungi, animals or substances produced by, or obtained from, microorganisms, viruses, microbial fungi or animals, e.g. enzymes or fermentates
- A01N63/20—Bacteria; Substances produced thereby or obtained therefrom
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
- C12N1/20—Bacteria; Culture media therefor
- C12N1/205—Bacterial isolates
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
- C12R2001/00—Microorganisms ; Processes using microorganisms
- C12R2001/01—Bacteria or Actinomycetales ; using bacteria or Actinomycetales
- C12R2001/425—Serratia
- C12R2001/43—Serratia marcescens
Definitions
- This invention relates generally to the protection of plants from pathogen attack, and particularly to protection from Oomycete pathogens, including treating plants with compositions from Serratia marcescens.
- the invention is concerned with a new group of antifungal and antimycotic compositions.
- the present invention provides Serratia marcescens and its isolates as being useful to control and prevent Oomycete infestation of plants, especially including the use of Serratia marcescens MSU-97 and serratamolide.
- the present invention further describes the production and isolation of serratamolide from Serratia marcescens MSU-97, as well as the range and efficacy of its antioomycetous activity.
- Serratamolide is a cyclic peptide known to have slight antibiotic properties, to inhibit phagocytosis by polymorphonuclear leukocytes and to increase potassium movement out of bacterial membranes. It has been discovered that serratamolide also has previously unknown antioomycetous activity against specific plant pathogens.
- the invention provides compounds for use in protection of plants from Oomycete pathogens.
- the invention also provides a method for making the compounds of the invention and an environmentally desirable method of controlling and preventing Oomycete infestation of plants by using the compounds of the invention.
- the invention further provides an environmentally desirable method of controlling and preventing Oomycete infestation of plants by administering the compounds of the invention to plants.
- the present invention provides a method for the protection of plants from Oomycete pathogens which comprises treating the plants with an effective amount of one or more isolates of Serratia marcescens.
- the present invention also provides an isolated serratamolide from Serratia marcescens compositions and use of the serratamolide for the protection of plants from Oomycete pathogens.
- FIG. 1 shows the structure of serratamolide.
- FIG. 2 shows the structure of oocydin A (no absolute stereochemistry is implied).
- FIG. 3 is a chromatogram of antioomycetous compounds produced by S. marcescens MSU-97 isolated and characterized against P. ultimum. Growth of S. marcescens was in soytone medium.
- A oocydin
- B unknown component
- C serratamolide
- D unknown component. The presence of oocydin was confirmed by co- chromatography against an authentic standard. The presence of serratamolide was confirmed as described in EXAMPLE 2.
- FIG. 4 is a chromatogram showing separation of serratamolide by preparative
- FIG. 5 is a ⁇ -NMR spectrum of serratamolide obtained in 100% deuterated chloroform.
- FIG. 6 is a 13 C-NMR of serratamolide isolated from S. marcescens MSU-97.
- Serratamolide was dissolved in 100% deuterated chloroform. A serratamolide fraction hydrolyzed for 30 minutes in 0.3 N NaOH and rechromatographed by analytical HPLC showed the absence of a serratamolide peak. In addition, acid hydrolysis in 10 N HCl of the purified fraction released serine. Serine was identified by paper chromatography on
- FIG. 7 shows the hydrolysis in dilute base which hydrolyzes serratamolide to serratamic acid (serratamolide peak is absent in red overlay). Hydrolysis of the serratamolide peak in dilute base eliminated antioomycetous activity against P. ultimum
- FIG. 8 shows the growth of S. marcescens MSU-97 and prodigiosin and serratamolide production in PGP medium.
- S. marcescens MSU-97 grown in PGP medium initiated serratamolide production approximately 12 hours after inoculation of the culture.
- PGP medium the red pigment prodigiosin was produced during exponential growth and declined as cultures entered stationary phase.
- the present invention describes methods for the protection of plants from Oomycete pathogens by treatment of the plant with a pathogen effective amount of one or more isolates from Serratia marcescens which possesses antioomycetous activity against Oomycete plant pathogens.
- the isolate is any material from Serratia marcescens which exhibits antioomycetous activity against Oomycete plant pathogens but is more particularly Serratia marcescens MSU-97 or serratamolide, used alone, together, or in admixture or with oocydin A.
- effective amount is meant an amount sufficient to protect the plants from Oomycete pathogens.
- Serratia marcescens is a Gram-negative bacillus that occurs naturally in soil and water, as well as in the human intestines. Methods of identifying and classifying S. marcescens are known in the art. Falkiner FR (1997) J. Med. Microbiol. 46:903-12. Growth of Serratia marcescens is accompanied by the production of a characteristic red tripyrrole pigment called prodigiosin. The production of a number of secondary metabolites is correlated with pigment synthesis. Prodigiosin is synthesized from amino acids, although the complete biosynthetic pathway is unknown. Bermingham, M. A., et al. (1971). J. Gen. Microbiol. 67, 319-324.
- Serratia marcescens isolate 97 is an epiphytic bacterium isolated from Rhyncholacis pedicillata, an aquatic plant native to Venezuela. See, EXAMPLE 1.
- a biologically pure culture of Serratia marcescens MSU-97 is deposited in the culture collection at Montana State University (MSU) and in other national collections.
- a deposit containing Serratia marcescens MSU-97 has been deposited with the American Type Culture Collection and assigned ATCC No. .
- the subject cultures are deposited under conditions that ensure that access to the cultures will be available during the pendency of the patent application disclosing them to one determined by the Commissioner of Patents and Trademarks to be entitled thereto under 37 C.F.R.
- the subject culture deposits will be stored and made available to the public in accord with the provisions of the Budapest Treaty for the Deposit of Microorganisms, i.e., they will be stored with all the care necessary to keep them viable and uncontaminated for a period of at least 30 years after the date of deposit or for the enforceable life of any patent which may issue disclosing the cultures plus 5 years after the last request for a sample from the deposit.
- the depositor acknowledges the duty to replace the deposits should the depository be unable to furnish a sample when requested, due to the conditions of the deposits. All restrictions on availability to the public of the subject culture deposits will be irrevocably removed upon granting of a patent disclosing them.
- compositions of the invention contain serratamolide (FIG. 1), which has antioomycetous activity, as shown in EXAMPLE 2.
- concentration of serratamolide is between 6 and 100 ⁇ g/ml.
- compositions of the invention may also contain a mono-chlorinated lipophilic macrocyclic lactone, oocydin A (FIG. 2), which was isolated from Serratia marcescens. See, Strobel, G. et al. (1999) Microbiol. 145: 3557-3564. In culture, Serratia marcescens MSU-97 produces oocydin A that can be recovered from the culture medium. Overall, it appears that oocydin A has selective lethal activity against Oomycetes at MICs lower or similar to those noted for metalaxyl. Oocydin is fully described in U.S. Application Serial No. 09/858,871, filed May 17, 2001, the disclosure of which is incorporated herein by reference.
- compositions or isolates of the invention may also contain prodigiosin, a red pigment produced by Serratia marcescens.
- the compounds of the invention may be in a form containing culture medium from which Serratia marcescens MSU-97 has been cultured (see, EXAMPLE 1).
- the compound of the invention may further contain an agriculturally acceptable carrier.
- the compound of the invention may be in a form especially prepared for administration to plants, such as the formulations containing solvents, solid carriers and, if appropriate, surface-active compounds (surfactants) (see, below).
- surfactants see, below.
- the Stramenophila are the Labyrinthulomycota, which have a thallus that is a network of branched tubes within which amoeboid cells crawl. Also among the Stramenophila are the Hyphochytriomycota, which have a thallus that is single-celled or rhizoidal and have motile cells with a single anterior tinsel type fiagellum.
- the Oomycetes are the largest group of Stramenophila. Oomycetes have a thallus that is filamentous with coenocytic hyphae or rarely single-celled or holocarpic. Oomycetes have motile cells, often with whiplash and tinsel flagellae.
- the Oomycetes include such genera as Leptomitus, Brevilegnia, Aphanomyces, Achlya, Saprolegnia, Pythium, Plasmopara, Phytophthora, and Peronospora.
- Oomycetes that have undergone extensive life cycle studies have been found to be diploid in the vegetative phase with meiosis occurring during gametogenesis.
- "Oomycota” means "egg fungi”, a term that refers to the large round oogonia, or structures containing the female gametes. Oomycetes are oogamous, producing large non- motile gametes called eggs, and smaller gametes called sperm.
- the Oomycota were once classified as fungi, because of their filamentous growth, and because they feed on decaying matter like fungi.
- the cell wall of Oomycetes is not composed of chitin, as in the fungi, but is made up of a mix of cellulosic compounds and glycan.
- the nuclei within the filaments are diploid, not haploid as in the fungi.
- Oomycetes are found all over the world in fresh-water and salt-water habitats. Oomycetes absorb their food from the surrounding water or soil, or may invade the body of another organism to feed. The presence of free water or high humidity is important for the development and the pathogenicity of these organisms. Some of the terrestrial Oomycetes are among the most important plant pathogens.
- Oomycetes are important parasites on flowering plants. These include root rotting fungi, seedling dampening mold, blister rusts, white rusts (Albugo, such as A. Candida), water molds and the downy mildews (including Peronospora tabacina) that attack mainly potatoes, tomatoes, vines, hops, maize, sugar beet, tobacco, vegetables, lettuce, but also bananas, rubber, as well as lawns and ornamentals. Plant diseases caused by Oomycetes can have a major impact on human populations. Plasmopara viticola causes the downy mildew of grapes that, in the late 1870s, almost wiped out the French wine industry. Phytophthora infestans causes the late blight of potato that, in the summer of 1846, caused the great Irish Potato Famine.
- Phytophthora destroy eucalyptus, avocado, pineapples, and other tropical crop plants.
- Phytophthera parasitica causes black shank disease.
- Root rot of ornamental plants, such as poinsettia can be caused by Pythium aphanidermatum, P. debaryanum, P. irregular, P. megalacanthum, P. oligandum, P. perniciorum, P. polymastum and P. utimum, and by Phytophthora parasitica.
- Quick oak decline and ornamental plants are subject to attack by phytophthora ramorum.
- the compounds of the invention and the methods of using the compounds are useful for protecting or treating Oomycete-related diseases affecting cereals (maize, wheat, barley, rye, oats, rice, sorghum and related crops); beet (sugar beet and fodder beet); pomes, stone fruit and soft fruit (apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries and blackberries); leguminous plants (beans, lentils, peas, soybeans); oil plants (rape, mustard, poppy, olives, sunflowers, coconut, castor oil plants, cocoa beans, groundnuts); cucumber plants (marrows, cucumber, melons); fiber plants (cotton, flax, hemp, jute); citrus fruit (oranges, lemons, grapefruit, mandarins); vegetables (spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, paprika); lauraceae (avocados, cinnamon, camphor); or
- the invention offers a number of advantages and uses stemming from the easily controlled administration of the compounds of the invention on in plants or plant tissue, such as in the manner of U.S. Pat. No. 5,856,154, 6,031,153, and 6,228,884. Administration may be accomplished simply by applying the compound of the invention to the plant tissue, or to the plant or part of the plant in such a manner and in such an amount as to be effective. For example, application of the compound of the invention can be made to the entire plant (i.e., stem and both sides of the leaves). If administration to the roots is desired, application to the seeds or the soil around the seeds or roots is also possible.
- the compounds of the invention can be applied in pure form, in solution or suspension, as powders or dusts, or in other conventional formulations used agriculturally or in bioreactor processes. See, U.S. Pat. No. 5,856,154.
- the compounds of the invention can be prepared in formulations in a known manner, for example by intimately mixing and/or grinding the active ingredients with extenders, such as, for example, with solvents, solid carriers and, if appropriate, surface-active compounds (surfactants). See, U.S. Pat. No. 6,228,884.
- Suitable carriers and additives can be solid or liquid and correspond to the substances expediently used in formulation technology, such as, for example, natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers. See also, U.S. Pat. No. 6,228,884.
- Such formulations may include solid or liquid carriers, that is, materials with which the regulator is combined to facilitate application to the plant, tissue, cell or tissue culture, or the like, or to improve storage, handling or transport properties. Examples of suitable carriers include silicates, clays, carbon, sulfur, resins, alcohols, ketones, aromatic hydrocarbons, and the like.
- the regulator formulation may include one or more conventional surfactants, either ionic or non-ionic, such as wetting, emulsifying or dispersing agents.
- the compounds of the invention may be applied as a spray to plant leaves, stems or branches, to seeds before planting or to the soil or other growing medium supporting the plant.
- the administration of the compounds of the invention can be guided by the administration of acylalanine fungicides, such as metalaxyl (N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-DL-alanine methyl ester); benalaxyl (N-(2,6-dimethylphenyl)-N-(phenylacetyl)-DL-alanine methyl ester); furalaxyl (N-(2,6dimethylphenyl)-N-(2-furanylcarbonyl)-DL-alanine methyl ester).
- metalaxyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-DL-alanine methyl ester
- benalaxyl N-(2,6-dimethylphen
- acylalanine fungicides are foliar application, in which the foliage and the growing plant being treated with the active ingredient. See, U.S. Pat. No. 6,228,884.
- the active ingredient is incorporated into the soil directly by applying it in liquid form, or, for example, by means of granules.
- a preferred method of applying the compounds of the invention is to the aerial parts of the plant, especially the foliage (foliar application). See, U.S. Pat. No. 6,228,884. Number and rate of application depend on the biological and climatic environmental conditions for the pathogen.
- the compounds of the invention may reach the plant via the soil through the root system, by drenching the site of the plant with a liquid composition, or by incorporating the substances into the soil in solid form, for example in the form of granules (soil application).
- the compounds of the invention are employed as pure active ingredient or, preferably, together with the adjuvants conventionally used in the art of formulation and is therefore processed in a known manner to give, for example, emulsion concentrates, spreadable pastes, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules, or by encapsulation, for example in polymeric substances.
- the methods of application such as spraying, atomizing, dusting, scattering, brushing on or pouring, as well as the type of the compositions, are selected to suit the intended aims and the prevailing circumstances.
- the agrochemical compositions comprise 0.1 to 99%, in particular 0.1 to 95%o, of the active ingredient 99.9 to 1%, in particular 99.9 to 5%, of a solid or liquid additive, and 0 to 25%, in particular 0.1 to 25%. See, U.S. Pat. No. 6,228,884. While concentrated compositions are more preferred as commercially available goods, the end consumer uses, as a rule, dilute compositions.
- the compounds of the invention can also be applied to plants in combination with another agent that may afford some benefit to the plant.
- the compounds of the invention can be admixed with a fertilizer and then applied.
- Rhyncholacis pedicillata is a small highly specialized aquatic plant of the family Podostemaceae that grows in colonies and thrives in some of the brown-black rivers of the Venezuelan-Guyana.
- R. pedicillata is 0.2-1.0 m in size and it has a bulbous base that anchors the plant to a rock. Its stems are multibranched, are lacy-like, and covered with numerous small leaves.
- Close examination of individual plants in the Carrao River revealed animal or environmentally inflicted wounds on the stems. Normally, such wounds would serve as entry points for one or more pathogenic Oomycetes. However, little or no disease symptoms on the plants were observed.
- S. marcescens is a relatively common microorganism. Regular isolates of it were also screened in the antioomycetous plate test. Neither ATCC isolate 1009, nor MSU isolate 69 demonstrated any antioomycetous activity diffusing from the culture after 3 days of exposure to P. ultimum. This straightforward antifungal test revealed that the likelihood of finding one or more novel antioomycetous substances from isolate 97 of S. marcescens was extremely unlikely.
- the surface characteristics of the bacteria on the plant were identical to those on bacterial surfaces of pure cultures of authentic S. marcescens (isolate 97).
- the bacterial surface characteristics included multiple small projections as well as a generally relatively rough cell surface. This does not appear to be common in bacteria and this characteristic may serve as a means to help locate and identify S. marcescens on the surface of its host.
- the size and shape of the bacterial cells on the plant and those of the authenticated culture appear to be identical. Since S. marcescens was primarily recovered from the plant surface and not from internal tissues, it was considered more epiphytic than endophytic in its relationship to the plant. EXAMPLE 2
- Serratamolide [58] The production and localization of serratamolide in Serratia marcescens MSU-97 as well as the range and efficacy of its antioomycetous activity were examined. Serratamolide was found to have previously unknown antioomycetous activity against specific plant pathogens.
- Serratamolide is a cyclic peptide (Wasserman, H. H., et al. (1962) J Am. Chem. Soc. 84, 2978-2982).
- Serratamolide was isolated from liquid cultures of Serratia marcescens and purified from a 50% > to 75%o methanol solid phase extraction (SPE), then separated by preparative HPLC (FIG. 3).
- PGP peptone-glycerol-phosphate
- Zone of Clearing The zone of clearing on a PDA plate measured antioomycetous activity. Oomycete cultures were grown for three to five days on PDA plates at 23 °C to produce active colonies. Compounds to be tested were placed on a PDA plate in 10 to 20 ⁇ l of methanol and allowed to dry. Then 7-mm agar plugs were cut from agar plates containing the fungal strain to be tested and seeded 10 to 15 mm away from the applied test material. Antioomycetous activity was evidenced as a zone of inhibition of growth around the test compound.
- Prodigiosin Isolation After collecting the 75% methanol fraction containing serratamolide from the solid phase cartridge, prodigiosin was eluted using CHC1 3 methanol (1:2), and the spectra determined on a UVICON 860 scanning UV spectrophotometer. Pigment concentration was determined by the absorbance at 540 nm. [65] In this EXAMPLE, prodigiosin synthesis reached a maximum at 48 hours and then declined. Serratamolide was not produced prior to pigment synthesis, but continued after pigment synthesis decreased (FIG. 8).
- Serratamolide is a previously discovered cyclic depsipeptide known to have slight antibiotic properties, to inhibit phagocytosis by polymorphonuclear leukocytes, and to increase potassium movement out of bacterial membranes.
- the data in this EXAMPLE shows that serratamolide is present in sufficient concentration during growth of S. marcescens MSU-97 to contribute significantly to the antifungal activity exhibited by this organism.
- Pieces of agar containing the cultures were transferred to sterile microfuge tubes containing 0.5 ml sterile distilled water and broken up using a sterile Teflon pestle. 100 ⁇ l of PD broth containing the mycelia was added to each well, and growth inhibition was monitored over 3 days. At the end of 3 days cultures were transferred to a ground glass homogenizer, gently broken up, diluted in distilled water and the optical density measured using a Spectronic 20 spectrophotometer at 660 nm. The minimum inhibitory concentration was determined as the concentration of serratamolide compound needed to effect a 10% reduction in growth. [71] Serratamolide was active against Oomycetes only (e.g., P. cactorum, P. capsici, P. ultimum).
- Rhizoctonia solani 100
- Botrytis cinera 100
- This EXAMPLE shows the ability of extracts of Serratia marcescens MSU-97 to effectively limit or prevent infection of the ornamental plant Vinca (Catharanthus roseus) by the pathogen Phytophtora parasitica.
- Phytophtora parasitica is a virulent pathogen of Vinca, except in those varieties where resistance has developed. Infection of lateral stem tissue is common and is followed by rapid damage to and death of stem tissue below the site of infection. Sometimes the plant will respond by limiting the infection at a node and abscissing leaf and stem tissue. In more severe cases, the entire plant may die. Infection by P. parasitica is readily induced by growing active cultures of the pathogen in a sterile capsule and inverting the capsule over a cut stem or petiole for a period of 24 hours. This infection method provides a ready test system for evaluating the efficacy of a particular compound to either prevent or cure infection by this pathogen.
- Serratia marcescens MSU-97 was grown for a period of 12 days according to the method of Strobel, G. et al. (1999) Microbiology 145: 3557- 3564. Cultures were transferred to 250 ml centrifuge bottles and centrifuged in a Sorval Instruments GSA rotor at 20,000 x g for 15 minutes to remove the cells. The supernatant was then decanted and lyophilized almost to dryness. The culture medium was acidified to a pH of 3.0 using 2N HCl and brought to 50%> methanol (v/v) (Fisher Chemical).
- This solution was then passed through a 6 ml x 1000 mg Bond Elut C-18 solid phase extraction (SPE) cartridge Varian Instruments).
- SPE Bond Elut C-18 solid phase extraction
- the column was prepared for use by washing it with 100%) methanol followed by 10 ml of 18 megohm water, and 10 ml of 50% methanol.
- the column was then rinsed using 6 ml of 50% methanol.
- the compounds were then eluted from the SPE cartridge using 10 ml of 100% methanol, lyophilized to dryness, and weighed.
- MSU-97 medium was applied directly to the cut stem of each of 8 plants.
- 10 ⁇ l of methanol, the solvent for MSU-97 extract was applied to each of 8 plants as a positive control and allowed to dry. Leaves were excised from lateral stems of
- capsules containing active cultures of P. parasitica were inverted over four plants of each of the treatments, yielding a total of six treatments with four replications, where each plant was treated as a replication.
- test 1 the pathogen was left in contact with the plant for 24 hours, the capsule removed, and the plants evaluated for damage five days after the initiation of the test. The test was repeated twice, and the data is the average of the replicated treatments for two tests.
- test 2 In test 2, a similar design was employed, but the cultures of P. parasitica were left in contract with the stems throughout the 5 -day period of the trial.
- Step gradient used in separation of bioactive components ofS. marcescens MSU-97.
Abstract
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AU2002257272A AU2002257272A1 (en) | 2001-05-17 | 2002-05-15 | Method to protect plants from oomycete pathogens with serratia marcescens |
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Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5869038A (en) * | 1992-03-26 | 1999-02-09 | The Minister Of Agriculture, Fisheries And Food In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland | Biological control of fungal post harvest diseases with bacteria |
US6060051A (en) * | 1997-05-09 | 2000-05-09 | Agraquest, Inc. | Strain of bacillus for controlling plant diseases and corn rootworm |
-
2002
- 2002-05-15 AU AU2002257272A patent/AU2002257272A1/en not_active Abandoned
- 2002-05-15 WO PCT/US2002/015195 patent/WO2002091825A2/en not_active Application Discontinuation
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5869038A (en) * | 1992-03-26 | 1999-02-09 | The Minister Of Agriculture, Fisheries And Food In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland | Biological control of fungal post harvest diseases with bacteria |
US6060051A (en) * | 1997-05-09 | 2000-05-09 | Agraquest, Inc. | Strain of bacillus for controlling plant diseases and corn rootworm |
Non-Patent Citations (1)
Title |
---|
HASSALL ET AL.: 'The conformation of serratamolide and related cyclotetradepsipeptides in solution' JOURNAL CHEM. SOC. B no. 9, 1971, pages 1757 - 1761, XP002958222 * |
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