WO1999040790A1 - Procede de traitement de plantes cotyledonees - Google Patents

Procede de traitement de plantes cotyledonees Download PDF

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Publication number
WO1999040790A1
WO1999040790A1 PCT/US1998/009027 US9809027W WO9940790A1 WO 1999040790 A1 WO1999040790 A1 WO 1999040790A1 US 9809027 W US9809027 W US 9809027W WO 9940790 A1 WO9940790 A1 WO 9940790A1
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WO
WIPO (PCT)
Prior art keywords
chitosan
matrix polymer
polymer
oligomers
plant
Prior art date
Application number
PCT/US1998/009027
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English (en)
Inventor
George E. Heinsohn
August S. Bjornson
Original Assignee
Dcv, Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from PCT/US1998/002725 external-priority patent/WO1998034464A2/fr
Application filed by Dcv, Inc. filed Critical Dcv, Inc.
Priority to AU73673/98A priority Critical patent/AU7367398A/en
Publication of WO1999040790A1 publication Critical patent/WO1999040790A1/fr

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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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
    • A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P21/00—Plant growth regulators
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A40/00—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production
    • Y02A40/10—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production in agriculture

Definitions

  • the Invention is directed to a method for treating cotyledonous plants to improve the yield, health, and vigor of the plant by spraying on the leaves an aqueous solution of chitosan oligomers in a matrix polymer.
  • Chitosan salts have been shown to induce synthesis of the terpenoid phytoalexins which are closely involved in the biosynthesis of growth hormones such as gibberelic acid and abscisic acid .
  • Chitosan salts also induce activation of genes which produce chitinase and glucanase enzymes that are known to be fungal inhibitors and to play a role in pollen development and seed germination, as well as activation of genes which produce protease inhibitors that help protect the plant from insect attack. On a macroscopic scale, these changes translate into enhanced root development, reduced lodging (plants falling over before harvest), enhanced yield, and greater resistance to certain plant diseases.
  • US 4,812,159 discloses treatment of soil in the seed planting zone with a solution of chitosan, application of a chitosan solution to plant seeds, treatment of soil in the seed planting zone with a mixture of solid chitosan and a solid acid , treatment of soil in the seed planting zone with a solid chitosan salt , and application of chitosan salts to the leaves of emerging plants.
  • US 4,964,894 which is a continuation-in-part of US 4,812,159, describes again the same techniques noted above and then discloses a procedure involving seed germination studies for identifying non-phytotoxic acids .
  • Another technique using chitosan is described in US 5,554,445 (Kivekas, Struszczyk) which involves spraying seeds with a liquid dispersion of microcrystalline chitosan, followed by drying to form a polymer film around the seed.
  • US 4,886,541 discloses the application of a chitosan preparation to wheat seed in order to enhance yield, reduce lodging, and enhance root development.
  • US 4,978,381 (Hadwiger) and US 5,104,437 (Hadwiger) describe the same techniques for seed treatment and provide additional examples to extend the method to other cereal crops such as rice, oats, barley, and rye.
  • Chitosan has been employed in agriculture for purposes other than its ability to enhance crop yields. For example, it has demonstrated ability as a bactericide against a variety of microorganisms and has been employed extensively for this purpose.
  • the use of chitosan to inhibit bacteria- nucleated frost damage is disclosed in JP 07179843 A (assigned to Daiiche Seimo KK), and US 5,374,627 discloses the use of a chitosan hydrolysate of molecular weight (MW) 10,000- 50,000 prepared by high- temperature , acid-catalyzed degradation of chitosan as an effective agent for protecting plants against a number of plant diseases such as bacterial soft rot in vegetables , spring deadspot in turfgrass , and bacterial grain rot in rice.
  • MW molecular weight
  • US 5,726,123 discloses a method for treating plants by foliar application of a solution containing both a chitosan salt and oligomers of chitosan that results in increased yield, better draught resistance, and improved overall vigor.
  • the chitosan salt is prepared from chitosan of molecular weight greater than 50,000 amu (atomic mass units, daltons) and an acid that forms a water-soluble chitosan salt .
  • the chitosan oligomers are defined as short fragments of chitosan chains having a degree of polymerization of 2-50, which corresponds to a molecular weight of approximately 320-10,000 amu.
  • This invention is directed to the application of a solution containing both chitosan oligomers and a water soluble polymer to the foliage of cotyledenous growing plants to enhance their yields. Plants so treated are healthier, more drought resistant, and many varieties enjoy an extended production period. The treatment may be repeated throughout the growth cycle of the plant, especially during critical stages of plant growth such as flowering, seed formation, and ripening.
  • the invention is, therefore, directed primarily to a method for improving the yield, health, and vigor of growing cotyldeonous plants comprising spraying onto the foliage between appearance of the first true leaves and completion of the harvest of the plant or fruit therefrom an aqueous solution containing dissolved therein 0.01 to 5.0% chitosan oligomers and a water soluble polymer.
  • the application is repeated before harvesting the plant or useful portion thereof.
  • a chitosan salt applied to the foliage of a plant would, therefore, have to penetrate the epidermal layers in order to initiate any systemic processes. It is problematic how a very large molecule such as a chitosan salt of >50,000 amu would be able to effect epidermal penetration.
  • chitosan salt serves mainly as a matrix to bind the oligomers to the plant and to inhibit loss of water-soluble oligomers from the plant during rainfall or heavy dew.
  • the chitosan salt also provides a minor source of chitosan oligomers derived by the natural degradation processes that cleave the chitosan chains into smaller and smaller fragments.
  • chitosan salt may be replaced by other polymers (matrix polymers) that are able to keep the chitosan oligomers from being washed from the plant upon exposure to water, and which may possess other advantages over chitosan salts in particular applications.
  • matrix polymers polymers that are able to keep the chitosan oligomers from being washed from the plant upon exposure to water
  • chitosan salts offer the advantages of serving as a continuous source of small quantities of chitosan oligomers through degradative processes, and becoming more moisture resistant with the passage of time, they have the disadvantage of forming aqueous solutions of very high viscosity, even at low concentration. Solutions of other polymers at equivalent concentration can have lower viscosity, thereby avoiding the disadvantages noted above.
  • Chitosan salts are particularly well suited to the purpose of protecting chitosan oligomers from rainfall and dew.
  • films formed from chitosan salts of volatile acids become more water-insoluble as the acid evaporated.
  • the initial film of water-soluble chitosan salt which is formed on the leaf surface as the foliar spray dries, becomes progressively less water- soluble and, therefore, more resistant to rainfall and dew with the passage of time.
  • the chitosan oligomers contained within the chitosan salt film become progressively less susceptible to being washed from the leaf by rainfall or dew. The elapsed time over which this occurs depends on the volatility of the acid and on the drying conditions encountered in the field.
  • the ability to keep chitosan oligomers bound to the plant and protected from moisture is not limited to salts of chitosan with volatile acids. Evaporation is not the sole mechanism for loss of acid from a chitosan salt film. Acid may also be removed from the chitosan salt film by biodegradation, through degradation by ambient conditions such as by hydrolysis and/or photolysis, or by deliberate treatment with basic materials such as ammonia and calcium carbonate which may be incorporated in the spray or introduced as a post treatment. Consequently , almost any acid which forms water soluble salts with chitosan is suitable. A further description of suitable acids is detailed below.
  • chitosan salts are indeed suitable for protecting chitosan oligomers from dew and rainfall, there are associated disadvantages caused by the high viscosity of chitosan as previously noted.
  • concentrations of active ingredient comparable to other agrichemical products (30%-80% wt.)
  • a relatively small amount of chitosan salt is sufficient to bind the oligomers to the plant and protect them from moisture, thereby avoiding high viscosity.
  • Chitosan oligomers may be embedded in a wide variety of water soluble polymers other than chitosan salts and still be protected from rainfall and dew by the slow rate at which the polymer dissolves. Provided that the moisture exposure is of relatively limited extent (as is often the case with dew or light showers), the polymer, by its slowness in dissolving, will provide protection for the oligomers even though it would ultimately fail under more strenuous conditions such as prolonged periods of heavy rainfall .
  • Chitosan Oligomers may be embedded in a wide variety of water soluble polymers other than chitosan salts and still be protected from rainfall and dew by the slow rate at which the polymer dissolves. Provided that the moisture exposure is of relatively limited extent (as is often the case with dew or light showers), the polymer, by its slowness in dissolving, will provide protection for the oligomers even though it would ultimately fail under more strenuous conditions such as prolonged periods of heavy rainfall .
  • chitosan oligomers is intended to refer to those homopolymers and copolymers of D-glucosamine and N-acetyl-D- glucosamine having a degree of polymerization (DP) of 2 to 50 corresponding to molecular weight of about 320 to 10,000 amu.
  • DP degree of polymerization
  • Kitasatosporia N174 to a solution of chitosan acetate at 37-55C. After 31 hr., the mixture was heated to 85C to denature the enzyme, and the product concentrated under vacuum at 35-40C and then lyophilized to dryness. Size exclusion chromatography on a Supelco-TSK Column G-Oligo-PW with a mobile phase containing 0.03 M acetic acid and 0.2 M sodium sulfate revealed that 41% of the resolved oligomers were of DP (degree of polymerization) ⁇ 7 and 59% of DP 6-28.
  • Suitable polymers for forming a matrix around the chitosan oligomers must be environmentally innocuous, and also be water soluble in order to facilitate preparation of a solution to spray on a plant . These polymers must also be able to attach to the surface of the leaf , and should therfore be capable of forming hydrogen bonds with polar sites such as -OH on the leaf surface.
  • Polymers containing -OH, -NH, or other polar functional groups such as carbonyl and amido groups are capable of such hydrogen bonding.
  • a detailed review of structural features essential to hydrogen bonding is found in Advanced Organic Chemistry by J. March, McGraw-Hill, N.Y.,N.Y.,1977, pp. 75-78, hereby incorporated by reference.
  • the polymer In order to prevent the oligomers from being washed from the plant by moderate rainfall or dew, the polymer must dissolve slowly enough in water to provide the necessary protection under field conditions . Different chemical classes of water soluble polymers vary greatly in the rates at which they dissolve.
  • suitable candidates for use as matrix polymers are those which (1) can be dissolved at a concentration of 0.5% wt. or higher in water, (2) are environmentally innocuous, (3) contain functional groups capable of forming hydrogen bonds, and (4) meet the following insolubility criteria:
  • suitable matrix polymers may be naturally occurring or synthetic, or mixtures thereof.
  • suitable members are soluble polysaccharides, alginates, polyhydroxyacids, polyaminoacids, polyaminosaccharides and soluble chitosan salts.
  • suitable naturally occuring polymers will be obvious to one skilled in the art.
  • synthetic polymers that will include suitable members are polyethers, polyacetals, polyesters, and polyamides, and poly(alkoxy cellulose) compounds, such as carboxy methyl cellulose.
  • suitable synthetic polymers will be obvious to one skilled in the art.
  • Chitosan as a Matrix Polymer
  • chitosan is a naturally occurring polymer found in many fungi, it is neither abundant nor readily isolated from natural sources in high purity.
  • chitosan is more readily obtained from chitin which, after cellulose, is the most abundant natural polymer.
  • Chitin is readily isolated from shellfish or insect exoskeletons, and is also found in mollusks and fungi.
  • a convenient method of obtaining chitosan from the chitin found in shellfish waste is described in U.S. 3,862,122 (Peniston).
  • compositions possible between the pure homopolymers, poly- N-acetyl-D-glucosamine and pure poly-D-glucosamine residues.
  • chitosan is intended to apply to copolymers of D- glucosamine and N-acetyl-D-glucosamine containing 0-35% N-Acetyl-D-
  • Inorganic acids which form water-soluble chitosan salts include the halogen acids and nitric acid but exclude sulfuric and phosphoric acids because they do not form water-soluble salts with chitosan.
  • Organic acids are preferred and include the following: lactic acid, glycolic acid, glutamic acid, and acetic acid. Acetic acid is most preferred because it is inexpensive, environmentally innocuous, and sufficiently volatile so that insolubilization of the corresponding chitosan salt is readily accomplished.
  • chitosan is typically prepared from shellfish and has a molecular weight measured in the hundreds of thousands, corresponding to polymer chains in which several thousand monomer units are linked together in ⁇ -1,4 fashion. Chitosan obtained from fungal sources is typically of somewhat lower molecular weight and may contain fractions with molecular weight as low as 50,000 amu (atomic mass units, daltons). The chitosan used in this study was obtained from shrimp or crab shell, and contained about 75-82% D-glucosamine residues which is typical of
  • additives refers to materials which may be optionally used to augment the effectiveness of the invention, but do not themselves have bio-activity. These include such materials as surfactants, wetting agents, defoaming agents, extenders, penetrants, activators, spreading agents, diluents, odorants, brightening agents and the like. It is particularly preferred to use a small amount of wetting agent in the compositions in order to obtain even distribution and wetting of the hydrophobic surface of the plant leaves. Such agents are usually used in concentrations of 0.01 - 0.1% by weight.
  • coadjuvant refers to materials that have a bio- activity that may be the same or different than the bio-activity of the chitosan salts. Such materials include fertilizers, fungicides, insect repellants, plant hormones, trace nutrients, pesticides, herbicides, and mixtures thereof. Both liquid and solid coadjuvants can be used in conjunction with water-soluble matrix polymers and oligomers, so long as the resultant aqueous compositions are sprayable.
  • a mixture of chitosan oligomers and a suitable matrix polymer may be applied to the foliage of growing plants by spraying with an aqueous solution containing appropriate amounts of these materials, or by other techniques which will be readily apparent to one skilled in the art.
  • the preferred technique is by solution spraying which eliminates the problems associated with settling of dispersions, or the dust inhalation hazard associated with applying solids to the
  • spray solutions having a matrix polymer concentration of 0.005 % to 5.0%, and most preferred to use solutions with concentration of 0.01% to 0.5 % . Solutions in this concentration range have viscosities compatible with the use of commercial spraying equipment . It is preferred to use solutions in which the weight ratio of chitosan oligomers to matrix polymer is in the range 0.01 tol ⁇ .0 and preferably in the range 0.05 to 5.0. Solutions in this range of concentration require an application rate of about 5-150 gallons per application per acre to achieve correct dosage which is compatible with the normal operation of commercial spraying equipment.
  • a concentrate containing chitosan oligomer and matrix polymer which may be diluted with water at the site of use prior to application to the plant.
  • the concentrate For typical field operations, it is convenient to dilute the concentrate with 100-500 volumes of water, so the concentrate should be prepared so as to contain the correct amount of chitosan oligomer and matrix polymer after such dilution.
  • a chitosan salt is chosen as the matrix polymer, a more specialized technique is employed since the chitosan must be converted into a salt during the dissolution process.
  • a preferred method when a chitosan salt is chosen as the matrix polymer is to form an aqueous dispersion of chitosan at a temperature of 45-85 C and preferably at 55-75C and to then add the acid. It is preferred that the reaction temperature be at least 45C in order to have a rapid rate of reaction without the necessity of using a large excess of acid. On the other hand, it is preferred that the reaction temperature not exceed 85 C in order to avoid
  • Chitosan oligomers, additives, and coadjuvants can be added to the reaction solution at any stage, but it is preferred that they be added after the reaction is complete and the solution has cooled in order to minimize any secondary reactions.
  • a wide variety of cotyledonous plants can be advantageously treated by the method of the invention, so long as the treatment is carried out in the manner described above.
  • Such plants include members of the genera Allium, Appium, Asparagus, Beta, Brassica, Capsicum, Citrullis, Cucurbita, Daucus, Repairria, ⁇ Lactuca, Lycopersicum, Phaseolus, Solamim, Spinachia and Zea.
  • the members of these genera of vegetables are asparagus, beans, beets, broccoli, carrots, celery, corn, egg plant, lettuce, melons, onions, pea, peppers, potatoes, spinach, squash, strawberries and tomatoes.
  • a further advantage of the invention is that the chitosan oligomers are non-toxic.
  • a matrix polymer that is of similar low toxicity e.g. a polysaccharide
  • the compositions of the invention will be non toxic to birds,
  • compositions 14 mammals, or humans. Moreover, the low toxicity level and easy biodegradability ofthe compositions act to prevent detrimental effects on the beneficial constituents of fertile soil layers. Accordingly, EPA has established an exemption from the requirement of a tolerance for residues of poly-D-glucosamine, when they are used in the production of raw agricultural commodities.
  • a chitosan acetate solution was prepared by vigorously stirring the appropriate amount of water at a temperature of 60 C and adding small flakes of chitosan containing 80 % D-Glucosamine residues at such a rate that the chitosan became wetted and dispersed throughout the liquid phase. Glacial acetic acid was then added in the ratio of 0.36 lb. of acetic acid per pound of chitosan. This represents a ratio of 1.03 equivalents of acetic acid per mole of amino function in the chitosan. The mixture was stirred at 60 C until substantially all the chitosan had dissolved , and the resulting solution then filtered through coarse cheese cloth to remove any adventitious particles.
  • the quantities of water and chitosan were chosen so that the chitosan concentration (exclusive ofthe acetate anion) was 5.0 %. A portion ofthe resulting solution was diluted to a chitosan concentration of 2.5 % and used in Examples I and II to illustrate the effect of chitosan salt only on the test plants. Solid chitosan oligomers were added to a second portion ofthe chitosan acetate solution equivalent to 5 % ofthe weight of chitosan (exclusive of acetate anion) and the mixture briefly agitated to ensure dissolution ofthe oligomers.
  • Treatment was commenced as soon as the plant had produced its first set of true leaves .
  • the true leaves are those which follow the emergent leaves (cotyledons) and which resemble the leaves ofthe mature plant in shape .
  • the treatment protocol was to spray the foliage ofthe plant until the top ofthe leaf surfaces were thoroughly wetted and solution began to drip from the leaf tips, and to repeat the treatment approximately every 2 weeks, as weather conditions allowed. As the plants increased in size, it was obviously necessary to use more chitosan spray solution to wet the leaves. It was estimated that the treatment rate was 10-20 gallons/acre for the initial treatment and 40-60 gallons/ acre at the end of treatment.
  • This test was designed to show the effect of plant treatment with a chitosan salt alone , compared to an untreated control and to treatment with a mixture of chitosan salt and chitosan oligomers.
  • the solution containing 2.5 % chitosan acetate described hereinabove was diluted 17:1 with water. Plants treated with this solution were designated group A.
  • the solution containing 2.5 % of chitosan acetate plus chitosan oligomers described in paragraph I was diluted 17:1 with water. Plants treated with this solution were designated group B.
  • Untreated plants were designated as group C.
  • Bell peppers ("Yolo Wonder") were treated with the appropriate solution when the first true leaves emerged 18 days after seeding. They were transplanted into the field in random block fashion such that each treatment protocol was replicated eight times with 10 plants in each replicate, so that each test was
  • 17 acetate and chitosan oligomers afforded an average of 777 fruits per 100 plants with 3.9 % classified by the grower as "small". This represents an increase of 25.1% in the number of fruits for the case where chitosan oligomers are incorporated into a chitosan acetate matrix compared to the case that where only the chitosan acetate matrix polymer was applied .
  • An additional benefit is that fewer undersized fruits were harvested in the case using chitosan oligomers.

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  • Life Sciences & Earth Sciences (AREA)
  • Plant Pathology (AREA)
  • Environmental Sciences (AREA)
  • Zoology (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Pest Control & Pesticides (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Botany (AREA)
  • Agronomy & Crop Science (AREA)
  • Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)

Abstract

L'application d'une solution aqueuse renfermant un matrice polymère et des oligomères de chitosane sur le feuillage de plantes en cours de croissance, permet d'augmenter la production de légumes, de tubercules, de céréales, de fruits et de fleurs. Les plantes ainsi traitées sont plus saines, plus robustes et plus résistante à la sécheresse, de nombreuses variétés bénéficiant d'une période de production plus étendue. Un traitement efficace et convenable de ces plantes consiste à pulvériser sur leur feuillage une solution renfermant 0,005 à 5,0 % en poids de matrice polymère et d'oligomères de chitosane, dans des quantités telles que le rapport en poids entre les oligomères de chitosane et la matrice polymère soit compris entre 0,01 et 10,0.
PCT/US1998/009027 1997-02-12 1998-05-08 Procede de traitement de plantes cotyledonees WO1999040790A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU73673/98A AU7367398A (en) 1997-02-12 1998-05-08 Method for treating cotyledonous plants

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
PCT/US1998/002725 WO1998034464A2 (fr) 1997-02-12 1998-02-12 Procede destine a traiter les plantes cotyledonees
GHPCT/US98/02725 1998-02-12

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WO1999040790A1 true WO1999040790A1 (fr) 1999-08-19

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001087067A1 (fr) * 2000-05-12 2001-11-22 The Procter & Gamble Company Compositions a base de polymer chitosan pour le soin des plantes
EP1185560A1 (fr) * 1996-10-15 2002-03-13 Noach Ben-Shalom Composition et technique de controle des maladies fongiques chez les vegetaux
WO2002085951A2 (fr) * 2001-04-19 2002-10-31 Technology Resource International Corporation Chitosane partiellement o-acetyle, partiellement n-acetyle substitue de maniere aleatoire soluble dans l'eau, des preparations de conservation contenant des chitosanes et des procedes de fabrication de ceux-ci
WO2003070008A1 (fr) * 2002-02-21 2003-08-28 Caldwell Bio Fermentation Canada Inc. Chitosane hydrolyse utile en tant que compose antimicrobien et utilisations de ce dernier
US6716970B2 (en) 2000-04-21 2004-04-06 Adjuvant Pharmaceuticals, Llc Water soluble, randomly substituted partial N-partial O-acetylated chitosan, preserving compositions containing chitosan, and processes for making thereof
US7125967B2 (en) 2003-10-08 2006-10-24 Adjuvant Pharmaceuticals, Llc Water-soluble chitosan having low endotoxin concentration and methods for making and using the same

Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6333310A (ja) * 1986-07-29 1988-02-13 Ihara Chem Ind Co Ltd 植物生長促進剤
JPS63216804A (ja) * 1987-03-05 1988-09-09 Meiji Seika Kaisha Ltd 植物の生長制御方法
JPS63297305A (ja) * 1987-05-28 1988-12-05 Katakura Chitsukarin Kk 種子のコ−テイング剤および種子の処理方法
WO1989007395A1 (fr) * 1988-02-19 1989-08-24 Bentech Laboratories, Inc. Traitement de plantes avec des sels de chitosan
EP0365279A2 (fr) * 1988-10-18 1990-04-25 Ciba Specialty Chemicals Water Treatments Limited Compositions pour l'agriculture
JPH03198702A (ja) * 1989-12-27 1991-08-29 Lion Corp 種子発芽促進方法
WO1992008741A1 (fr) * 1990-11-19 1992-05-29 Centre National De La Recherche Scientifique Composes a liberation progressive d'oligemeres de la glucosamine, procede de preparation et applications
JPH0565368A (ja) * 1991-09-06 1993-03-19 Bihoku Funka Kogyo Kk 低分子量キトサン含有植物機能調節用組成物
JPH07203771A (ja) * 1994-01-14 1995-08-08 Nishikawa Rubber Co Ltd 生分解性キトサン徐放材
JPH083011A (ja) * 1994-06-22 1996-01-09 Tadamoro Inoue 異種植物の接合促進剤
JPH09143013A (ja) * 1995-11-20 1997-06-03 Yaizu Suisan Kagaku Kogyo Kk 植物活力剤
US5726123A (en) * 1997-02-12 1998-03-10 Dcv Chitin Technologies, L.P. Method for treating cotyledonous plants

Patent Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6333310A (ja) * 1986-07-29 1988-02-13 Ihara Chem Ind Co Ltd 植物生長促進剤
JPS63216804A (ja) * 1987-03-05 1988-09-09 Meiji Seika Kaisha Ltd 植物の生長制御方法
JPS63297305A (ja) * 1987-05-28 1988-12-05 Katakura Chitsukarin Kk 種子のコ−テイング剤および種子の処理方法
WO1989007395A1 (fr) * 1988-02-19 1989-08-24 Bentech Laboratories, Inc. Traitement de plantes avec des sels de chitosan
EP0365279A2 (fr) * 1988-10-18 1990-04-25 Ciba Specialty Chemicals Water Treatments Limited Compositions pour l'agriculture
JPH03198702A (ja) * 1989-12-27 1991-08-29 Lion Corp 種子発芽促進方法
WO1992008741A1 (fr) * 1990-11-19 1992-05-29 Centre National De La Recherche Scientifique Composes a liberation progressive d'oligemeres de la glucosamine, procede de preparation et applications
JPH0565368A (ja) * 1991-09-06 1993-03-19 Bihoku Funka Kogyo Kk 低分子量キトサン含有植物機能調節用組成物
JPH07203771A (ja) * 1994-01-14 1995-08-08 Nishikawa Rubber Co Ltd 生分解性キトサン徐放材
JPH083011A (ja) * 1994-06-22 1996-01-09 Tadamoro Inoue 異種植物の接合促進剤
JPH09143013A (ja) * 1995-11-20 1997-06-03 Yaizu Suisan Kagaku Kogyo Kk 植物活力剤
US5726123A (en) * 1997-02-12 1998-03-10 Dcv Chitin Technologies, L.P. Method for treating cotyledonous plants

Non-Patent Citations (9)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Section Ch Derwent World Patents Index; Class A97, AN 73-05114U, XP002077212 *
DATABASE WPI Section Ch Week 8812, Derwent World Patents Index; Class C03, AN 88-080717, XP002077208 *
DATABASE WPI Section Ch Week 8842, Derwent World Patents Index; Class C03, AN 88-296419, XP002077210 *
DATABASE WPI Section Ch Week 8903, Derwent World Patents Index; Class C03, AN 89-020572, XP002077211 *
DATABASE WPI Section Ch Week 9141, Derwent World Patents Index; Class C03, AN 91-299396, XP002077209 *
DATABASE WPI Section Ch Week 9316, Derwent World Patents Index; Class C03, AN 93-129167, XP002077214 *
DATABASE WPI Section Ch Week 9540, Derwent World Patents Index; Class A97, AN 95-307044, XP002077213 *
PATENT ABSTRACTS OF JAPAN vol. 96, no. 5 31 May 1996 (1996-05-31) *
PATENT ABSTRACTS OF JAPAN vol. 97, no. 10 31 October 1997 (1997-10-31) *

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1185560A1 (fr) * 1996-10-15 2002-03-13 Noach Ben-Shalom Composition et technique de controle des maladies fongiques chez les vegetaux
EP1185560A4 (fr) * 1996-10-15 2002-11-04 Noach Ben-Shalom Composition et technique de controle des maladies fongiques chez les vegetaux
US6716970B2 (en) 2000-04-21 2004-04-06 Adjuvant Pharmaceuticals, Llc Water soluble, randomly substituted partial N-partial O-acetylated chitosan, preserving compositions containing chitosan, and processes for making thereof
US7683039B2 (en) 2000-04-21 2010-03-23 Adjuvant Pharmaceuticals, Llc Water soluble, randomly substituted partial N-, partial O-acetylated chitosan, preserving compositions containing chitosan, and processes for making thereof
WO2001087067A1 (fr) * 2000-05-12 2001-11-22 The Procter & Gamble Company Compositions a base de polymer chitosan pour le soin des plantes
WO2002085951A2 (fr) * 2001-04-19 2002-10-31 Technology Resource International Corporation Chitosane partiellement o-acetyle, partiellement n-acetyle substitue de maniere aleatoire soluble dans l'eau, des preparations de conservation contenant des chitosanes et des procedes de fabrication de ceux-ci
WO2002085951A3 (fr) * 2001-04-19 2003-02-06 Technology Resource Int Corp Chitosane partiellement o-acetyle, partiellement n-acetyle substitue de maniere aleatoire soluble dans l'eau, des preparations de conservation contenant des chitosanes et des procedes de fabrication de ceux-ci
WO2003070008A1 (fr) * 2002-02-21 2003-08-28 Caldwell Bio Fermentation Canada Inc. Chitosane hydrolyse utile en tant que compose antimicrobien et utilisations de ce dernier
US7125967B2 (en) 2003-10-08 2006-10-24 Adjuvant Pharmaceuticals, Llc Water-soluble chitosan having low endotoxin concentration and methods for making and using the same

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