WO2001087067A1 - Compositions a base de polymer chitosan pour le soin des plantes - Google Patents

Compositions a base de polymer chitosan pour le soin des plantes Download PDF

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Publication number
WO2001087067A1
WO2001087067A1 PCT/US2001/015181 US0115181W WO0187067A1 WO 2001087067 A1 WO2001087067 A1 WO 2001087067A1 US 0115181 W US0115181 W US 0115181W WO 0187067 A1 WO0187067 A1 WO 0187067A1
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WO
WIPO (PCT)
Prior art keywords
chitosan
gel
bioagent
molecular weight
composition
Prior art date
Application number
PCT/US2001/015181
Other languages
English (en)
Inventor
Henryk Struszcyk
Antoni Niekraszewicz
Henryk Pospieszny
Alojzy Urbanowski
Maria Wisniewska-Wrona
Magdalena Kucharska
Original Assignee
The Procter & Gamble Company
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
Application filed by The Procter & Gamble Company filed Critical The Procter & Gamble Company
Priority to EP01937294A priority Critical patent/EP1280410A1/fr
Priority to CA002407631A priority patent/CA2407631A1/fr
Priority to JP2001583545A priority patent/JP2004501098A/ja
Priority to AU2001263045A priority patent/AU2001263045A1/en
Publication of WO2001087067A1 publication Critical patent/WO2001087067A1/fr
Priority to US10/292,233 priority patent/US20030119672A1/en

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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

Definitions

  • the present invention relates to bioagent compositions for plant care. Treatment of plants with the compositions herein serves to inhibit the activity of pathogens toward the plants so treated and further stimulates the natural immunity of the treated plants against such pathogens.
  • the compositions herein also provide growth biostimulation for plants treated therewith.
  • the chitosan is used in aqueous solutions, chiefly in organic acids.
  • Such known chitosan-based agents may, as a consequence of their formulation, show phytotoxic action toward plants. Furthermore such formulations act insufficiently on fungal diseases in vivo. Given their form, such preparations selectively act on pathogenic fungi and do not display a controlled action on fungi in vivo without the possibility of simultaneously affecting various fungi strains.
  • Polish Patent Applications P.324094 and P.324095 both disclose bioagents for protecting plants against, respectively, bacterial and fungal diseases.
  • the bioagents disclosed in these patent applications are water suspensions of icrocrystalline chitosan containing 0.001-10% of microcrystalline chitosan with average molecular weight, respectively, of not less than 20 kD (P.324094) and lkD (P.324095); a water retention value (WRV) of not less than 100%, a deacetylation degree of not less than 65%, and an average particle size in the 1-100 ⁇ m range.
  • WRV water retention value
  • bioagents actively inhibit the development of bacterial and fungal pathogens which appear in the soil and/or on the plant by directly affecting the pathogens and promoting natural plant immunity. Since these bioagents are in the form of suspensions, these agents find only limited application possibilities and, due to the particle size of the chitosan therein, their plant protection potential is limited.
  • Polish Patent Applications P.269 984 and P.269 985 both disclose methods for limiting the infection caused by plant viruses.
  • plants prior to infection with mechanically transmitted viruses, are treated with chitosan having an average molecular weight of 5-200 kD.
  • the chitosan is in the form of either solutions in organic acids with a polymer concentration of 0.005-0.1% or suspensions of microcrystalline chitosan in water or organic fluids containing 0.005-0.01% of the polymer which has a water retention value of 100-500%.
  • the use of chitosan solutions in organic acids is not convenient because of the acidity and phytotoxicity toward plants and because is is not easy to remove the preparate with water.
  • the use of microcrystalline chitosan is limited with respect to the suspension form and particle size.
  • Polish Patent Application P.335454 discloses an agent for protecting plants against bacterial, fungal and viral diseases.
  • This agent comprises a chitosan gel with a pH in the range 6.3 to 7.0, containing not less than 0.001% chitosan having an average molecular weight not lower than 10 kD preferably 20-500 kD and deacetylation degree not lower than 65% preferably 70-95%.
  • the preparate demonstrates biological activity in inhibiting pathogens.
  • the agent can additionally contain some water-soluble polymers which facilitate the deposition of the agent on plants.
  • U.S. Patent 5,726,123 discloses a method to enhance the crop output of plants by applying an aqueous acidic solution of mixture of chitosan salts and added chitosan oligomers.
  • U.S. Patent 4,886,541 discloses a method for encapsulating grain seeds with chitosan salts to promote better plant rooting and increase of stem diameter.
  • U.S. Patent 4,964,894 discloses a plant growth regulator based on an aqueous acidic solution of chitosan salts or dry chitosan salts to be applied in the soil.
  • U.S. Patent 5,965,545 discloses a composition and a method for controlling the growth of fungal pathogens.
  • compositions and methods utilize a mixture of an aqueous, acidic or close to neutral solutions of chitosan salts with average molecular weight 200 kD and added oligoaminocarbohydrates with an average molecular weight in the 4-10 kD range.
  • chitosan-based agents fail to demonstrate an optimal biological activity in protecting plants against pathogens like fungi, bacteria, and viruses. Furthermore they do not exhibit a wide spectrum in plant care that would stimulate the growth of plants from germination to harvest.
  • the application of acidic aqueous solutions of chitosan in the known methods causes phytotoxic action on the plant and facilitates the removal of salts by water.
  • compositions useful for plant care can be in liquid or solid state.
  • compositions herein comprise at least 0.001%, and preferably 0.1% to 99.9%, by weight of chitosan polymer in certain forms and having certain chemical characteristics.
  • the chitosan polymer is utilized in the compositions in the form of particles of "microcrystalline" chitosan. Such particles are in the composition which has a pH of greater than 6.9. Microcrystalline chitosan particles of this type are those which have been prepared by a specific step-wise precipitation from aqueous acidic solutions of chitosan.
  • the chitosan polymer is utilized in the compositions herein as a gel-form chitosan salt which are in a composition having a pH of from 5.0 to 6.9.
  • gel-from chitosan salts can also be prepared by a specific step-wise precipitation process.
  • the chitosan polymer present in the compositions must have an average molecular weight of not less than 10 kD, a polydispersity degree not lower than 2 and a deacetylation degree not lower than 65%.
  • the chitosan polymer has a bimodal distribution of molecular weight and comprises a fraction of water-soluble oligoaminocarbohydrates having an average molecular weight less than 10 kD.
  • the chitosan component of the compositions herein is present in certain specific forms which generally result from the way in which the chitosan polymer is prepared. Such forms are those which are realized when the chitosan is precipitated from aqueous acidic chitosan solutions via a procedure involving the step-wise addition of neutralizing agent to such acidic solutions under shear agitation. Such a procedure is disclosed in Polish Patent Application No. P.340132 and in the concurrently filed PCT Application No. US/01/ (P&G Case CM-2550FL*)
  • MCCh microcrystalline chitosan
  • an aqueous solution is formed, generally containing at least 0.001% and preferably from 0.01% to 10.0% by weight of chitosan which can be provided by any conventional chitosan source.
  • This solution contains organic or inorganic acids and/or salts of such acids in an amount sufficient to maintain the solution at a pH which is low enough to completely solubilize the chitosan.
  • the aqueous solution of the first step is partially neutralized by adding a neutralizing agent while subjecting the solution to shear agitation.
  • the neutralizing agent addition and the agitation are sufficient to convert the solution into a continuous gel phase having a pH of from 5.0 to 6.9
  • the partially neutralized gel formed in the previous step is maintained under shear agitation for at least 10 seconds after the gel phase has been formed in order to homogenize the gel phase.
  • This agitated homogenized gel is then further neutralized under continuing agitation by addition of more neutralizing agent sufficient to raise the pH within the homogenized gel phase to above 6.9, preferably above 7.3. Agitation is preferably continued for at least another 10 seconds after this elevated pH is reached.
  • This forms a gel-like suspension of discrete particles of MCCh, and it is this gel-like suspension which can be used as the chitosan component of the bioagent compositions herein.
  • the chitosan particles used in this particular embodiment of the compositons herein are characterized as "microcrystalline” even though their degree of crystallinity is very low, and, in fact is much lower than the degree of crystallinity of many commercially available chitosan products which have a significant crystalline content.
  • the particles herein can be characterized as "activated” given their utility in the bioagent compositions herein.
  • the chitosan material of the particles which are produced is activated because it has a modified specific molecular structure having specific molecular weight and degree of polydispersity. It also has a supermolecular structure having certain morphological characteristics which provide porosity and ability to retain water in a capillary system.
  • microcrystalline chitosan (MCCh) particles are those which have been modified by their prepration process to be “activated.”
  • the chitosan polymer component may also be utilized as a gel-form chitosan salt.
  • Chitosan salts in gel form may also be produced by the process described above but one in which the final neutralization step is not used.
  • the homogenized continuous gel phase having a pH of from 5.0 to 6.9 is, in fact, a material which may also be used in the compositions herein without further converting this homogenized gel phase material to MCCh.
  • the chitosan in the compositions herein preferably have a molecular weight of from 15 to 1300 kD.
  • the chitosan polymer will also preferably have a polydispersity degree of from 3 to 6.
  • the chitosan polymer will also preferably have a deacetylation degree of from 75% to 95%.
  • the chitosan polymer such as prepared by the process steps outlined above may have a bimodal distribution of molecular weight.
  • the chitosan polymer prepared in the manner outlined above will generally also have a water-soluble fraction of oligomeric aminocarbohydrates within its polymeric structure. Such an oligomeric fraction will preferably have an average molecular weight within the range of from 0.179 to 1.79 kD.
  • bioagent compositions herein resides in their use of chitosan of controlled structure, especially a structure having the distribution of molecular weight with bimodal character and/or the presence of the oligomeric fraction. These features provide the multifunctional activity in inhibiting plant pathogens such as viruses, viroids, bacteria and fungi, both directly and indirectly, and a simultaneous stimulation of natural plant immunity against these pathogens. Furthermore, the bioagent compositions herein, both those using chitosan in the form of microcrystalline chitosan as well as those using gel chitosan salts, cause a biostimulation of plant growth from seed germination through seedlings up to the final form of plant or fruits. The joint action of the bioagent composition according to the present invention provides the desirable plant care activity.
  • chitosan bioagent allows, among other things, a controlled biodegradation of chitosan after its application as consequence of the presence of microorganisms or enzymes. Such biodegradation produces a suitable amount and types of bioactive oligoaminosaccharides which inhibit the growth of bacteria or fungi and also biostimulates the plants during their growth stages.
  • the molecular structure of the chitosan bioagent as polycationic provides a controlled, optimal effect against several fungi and also beneficially affects membranes of plants causing the stimulation of natural immunity to pathogens.
  • bioagent is its immediate action after its use, both in the inhibition of the disease pathogens as well as the stimulation of natural plant immunity and growth biostimulation.
  • Another advantage of the chitosan bioagent, both in microcrystalline chitosan form and as gel-form chitosan salts, is the long lasting effect of its use under changeable atmospheric conditions. These forms of chitosan protects the plants in homes as well as in gardens and fields.
  • Yet another advantage of the active bioagent chitosan used in the compositions herein is the high immunity imparted to the treated plants, even when used at concentrations as low as 0.001% wt.
  • the chitosan material also has a wide application range without any hazard for the environment, humans or other animals.
  • the chitosan bioagent in fact, permits the entire elimination of environmental pollution due to its natural origin and complete biodegradability. The plants and their fruits can be used shortly after the bioagent application without the risk of harmful residues.
  • the chitosan bioagent used in this the invention exhibits higher biological activity toward the treated plants, both in terms of protection and biostimulation, than do other known chitosan based agents.
  • the bioactivity of this chitosan bioagent stems from its controlled structure and its in situ reactions which prevent phytotoxic effects in plants.
  • Microcrystalline chitosan (MCCh) in a form of gel-like dispersion containing 0.94 wt% of polymer is used for plant care of the Rickowska variety of lettuce.
  • the MCCh-containing composition is used in the stages of seed germination, plant growth as well as lettuce protection.
  • the lettuce seeds are germinated in an aqueous dispersion of MCCh with differing concentrations for 3 days at 20°C.
  • the results of the germination test are presented in Table 1.
  • the soil used for lettuce seed germination is inoculated with fungi from the Botrytis cinerea strain.
  • the lettuce seeds are encrusted with a 0.1 wt% dispersion of MCCh and then dried at 35°C. These seeds are then introduced into the infected soil, and the germination power is estimated after 5 days, in comparison to unencrusted seeds placed in the same soil and used as a control.
  • the MCCh-treated seeds provided a 90% germination power whereas the control provided only 30 %.
  • MCCh is introduced by mixing and spraying into a soil sample comprising a mixture of deacidified peat and sand in a weight ratio of 1:1. Lettuce seeds are then sown in such soil. The biostimulation of plant growth in the greenhouse is estimated after 3 weeks. The results of such a test are presented in Table 2.
  • MCCh at a concentration of 0.001 wt% is used for spraying the lettuce 6 days before inoculation of the lettuce with the AIMV viruses. Such spraying inhibits the viruses' growth in 99.5% of the lettuce.
  • MCCh is used in vitro for inhibition of Clavibacter michiganense. In such testing MCCh provides a minimum inhibiting concentration (MIC) equal to 0.5. This testing shows that MCCh used for lettuce plant care does not cause any phytotoxic effect. This MCCH bioagent is excellent for care of lettuce plants during their growth period.
  • Microcrystalline chitosan (MCCh) in a gel-like suspension with 2.8% content of the polymer is used for plant care of the tomato species "Slonka".
  • MCCh is used for incrusting the tomato seeds; it is also applied on roots of seedlings and sprayed on the plants during growth.
  • the seeds are immersed for one hour in MCCh suspensions with different polymer concentrations and then dried afterwards.
  • the incrusted seeds are put into to a soil as in Example I, and the power of germination is estimated.
  • the results of germination are presented in Table 3.
  • the roots of the seedlings are immersed for 5 minutes in MCCh suspensions at various concentrations of MCCh. They are next bedded out in soil as in Example I. After two weeks growth in green-house, the roots and the green mass are weighed. The results are given in Table 4.
  • the tomato plants are sprayed with a gel-like suspension of MCCh and with a suspension of solid MCCh with varied concentration and after 24 hours inoculated with tobacco mosaic AIMV virus.
  • the results of the inhibition of infection are shown in Table 6.
  • the MCCh used for tomato plant care does not cause any phytotoxic effect. It is an ideal bioagent for plant care during the growth period. The harvested fruits are in excellent health condition.
  • the gel form of chitosan lactate is used for plant care of Rickowska variant lettuce plants.
  • the gel form is used during seed germination, plant growth as well as for plant protection.
  • the lettuce seeds are germinated in aqueous solutions of gel form of chitosan with different polymer concentrations during 3 days at 20°C. The results are presented in Table 8. Table 8.
  • This gel form of chitosan is used for plant dressing 24 hours before the plants are inoculated with AIMV viruses.
  • This gel form inhibits the virus infection to the extent of 99.5% and 98.8% respectively.
  • This gel form of chitosan lactate is used for the growth inhibition of Botrytis cinerea fungi using media rich in PDA components and poor media-SNA. At a concentration of 5 mg/cm 3 ' a 100% growth inhibition of this fungus is acheived.
  • the gel form of chitosan lactate does not cause any phytotoxic effect at any stage of the lettuce growth.
  • This bioagent is an excellent agent for plant care.
  • a gel form of chitosan acetate is used for the plant care of the tomato species 'Slonka".
  • the tomato seedlings before bed- out are immersed for 5 minutes in suspensions of this gel-like form of chitosan salt. They are next out-bedded in soil as in Example I. After 2 weeks growth in green house, the weight of roots and green mass is estimated. Results are presented in Table 10.
  • a gel form of chitosan salt with 0.1 wt% concentration is tested in vitro for its ability to inhibit the growth of Botrytis cinerea fungus. 80% and 85% inhibition of the fungus growth was attained for the rich PDA and weak SNA media respectively.
  • the gel form of chitosan acetate used for tomato plant care does not cause any phytotoxic effect. It is an ideal bioagent for plant care during the growth period. The fruits which are obtained are in very good health condition.

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne des compositions à base de bioagents pour le soin des plantes, que l'on peut utiliser pour le traitement des plantes et de leurs graines. Ce type de traitement sert à inhiber l'activité des agents pathogènes végétaux contre les plantes traitées, à stimuler l'immunité naturelle des plantes contre lesdits agents pathogènes et à provoquer une biostimulation de la croissance des plantes. Les compositions selon l'invention renferment un polymère chitosan pouvant se présenter soit sous la forme de particules de chitosan microcristallin dispersées dans une composition d'un pH supérieur à 6,9, soit sous la forme d'un gel à base de sel de chitosan dispersé dans une composition d'un pH compris entre 5,0 et 6,9. Quelle que soit sa forme, ledit polymère chitosan possède des caractéristiques de poids moléculaire, de degré de polydispersité et de degré de désacétylation spécifiées. De préférence, ledit polymère chitosan a une distribution de poids moléculaire bimodale et renferme une fraction d'oligoaminocarbohydrates solubles dans l'eau. Les caractéristiques du polymère chitosan utilisé dans ces compositions s'obtiennent par la neutralisation par étapes de solutions acides de chitosan et la précipitation du chitosan dans des conditions contrôlées.
PCT/US2001/015181 2000-05-12 2001-05-10 Compositions a base de polymer chitosan pour le soin des plantes WO2001087067A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
EP01937294A EP1280410A1 (fr) 2000-05-12 2001-05-10 Compositions a base de polymer chitosan pour le soin des plantes
CA002407631A CA2407631A1 (fr) 2000-05-12 2001-05-10 Compositions a base de polymer chitosan pour le soin des plantes
JP2001583545A JP2004501098A (ja) 2000-05-12 2001-05-10 植物管理のためのキトサンポリマー組成物
AU2001263045A AU2001263045A1 (en) 2000-05-12 2001-05-10 Chitosan polymer compositions for plant care
US10/292,233 US20030119672A1 (en) 2000-05-12 2002-11-12 Bioagent compositions for plant care

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
PL34013100A PL340131A1 (en) 2000-05-12 2000-05-12 Plant care biopreparation
PLP.340131 2000-05-12

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US10/292,233 Continuation US20030119672A1 (en) 2000-05-12 2002-11-12 Bioagent compositions for plant care

Publications (1)

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WO2001087067A1 true WO2001087067A1 (fr) 2001-11-22

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PCT/US2001/015181 WO2001087067A1 (fr) 2000-05-12 2001-05-10 Compositions a base de polymer chitosan pour le soin des plantes

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EP (1) EP1280410A1 (fr)
JP (1) JP2004501098A (fr)
AU (1) AU2001263045A1 (fr)
CA (1) CA2407631A1 (fr)
PL (1) PL340131A1 (fr)
WO (1) WO2001087067A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1989001288A1 (fr) * 1987-08-14 1989-02-23 Washington State University Research Foundation, I Procede de traitement de semences de cultures cerealieres au chitosan destine a augmenter le rendement, la croissance des racines et la resistance de la tige
WO1989007395A1 (fr) * 1988-02-19 1989-08-24 Bentech Laboratories, Inc. Traitement de plantes avec des sels de chitosan
WO1994003062A1 (fr) * 1992-07-29 1994-02-17 Novasso Oy Procede d'encapsulation de graines
WO1997009879A1 (fr) * 1995-09-14 1997-03-20 Bioestimulantes Orgânicos, Lda. Formule et procede faisant appel au chitosane pour ameliorer la resistance des plantes vis-a-vis des agents pathogenes et des agressions de l'environnement
WO1999040790A1 (fr) * 1998-02-12 1999-08-19 Dcv, Inc. Procede de traitement de plantes cotyledonees
US5965545A (en) * 1996-10-15 1999-10-12 State Of Israel, Ministry Of Agriculture, Agricultural Research Organization, The Volcani Center Compositions and method for controlling fungal disease in plants
WO2001019187A1 (fr) * 1999-09-14 2001-03-22 Instytut Włòkien Chemicznych Agent protegeant les plantes contre les maladies

Family Cites Families (1)

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Publication number Priority date Publication date Assignee Title
PL340132A1 (en) * 2000-05-12 2001-11-19 Procter & Gamble Method of obtaining modified microcrystalline chitosamine

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1989001288A1 (fr) * 1987-08-14 1989-02-23 Washington State University Research Foundation, I Procede de traitement de semences de cultures cerealieres au chitosan destine a augmenter le rendement, la croissance des racines et la resistance de la tige
WO1989007395A1 (fr) * 1988-02-19 1989-08-24 Bentech Laboratories, Inc. Traitement de plantes avec des sels de chitosan
WO1994003062A1 (fr) * 1992-07-29 1994-02-17 Novasso Oy Procede d'encapsulation de graines
WO1997009879A1 (fr) * 1995-09-14 1997-03-20 Bioestimulantes Orgânicos, Lda. Formule et procede faisant appel au chitosane pour ameliorer la resistance des plantes vis-a-vis des agents pathogenes et des agressions de l'environnement
US5965545A (en) * 1996-10-15 1999-10-12 State Of Israel, Ministry Of Agriculture, Agricultural Research Organization, The Volcani Center Compositions and method for controlling fungal disease in plants
WO1999040790A1 (fr) * 1998-02-12 1999-08-19 Dcv, Inc. Procede de traitement de plantes cotyledonees
WO2001019187A1 (fr) * 1999-09-14 2001-03-22 Instytut Włòkien Chemicznych Agent protegeant les plantes contre les maladies

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
A.T.WOJDYLA ET AL.: "EFFECTIVENESS OF CHITOSAN IN THE CONTROL OF SPHAEROTHECA PANNOSA VAR.ROSAE AND PERONOSPORA SPARSA ON ROSES AND MYROTHECIUM RORIDUM ON DIEFFENBACHIA", DE. FAC. LANDBOUWW. INIV. GENT, vol. 61, no. 2a, 1996, pages 461 - 464, XP001031898 *
See also references of EP1280410A1 *
STRUSZCZYK H: "SOME ASPECTS ON THE CREATION OF CHITOSAN BIOACTIVITY", ADVANCES IN CHITIN SCIENCES, XX, XX, vol. 2, 1997, pages 616 - 624, XP001030147 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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

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EP1280410A1 (fr) 2003-02-05
AU2001263045A1 (en) 2001-11-26
CA2407631A1 (fr) 2001-11-22
JP2004501098A (ja) 2004-01-15
PL340131A1 (en) 2001-11-19

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