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WO2019178632A1 - Composition liquide contenant une guanidine polymère - Google Patents

Composition liquide contenant une guanidine polymère Download PDF

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Publication number
WO2019178632A1
WO2019178632A1 PCT/AT2019/060098 AT2019060098W WO2019178632A1 WO 2019178632 A1 WO2019178632 A1 WO 2019178632A1 AT 2019060098 W AT2019060098 W AT 2019060098W WO 2019178632 A1 WO2019178632 A1 WO 2019178632A1
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WO
WIPO (PCT)
Prior art keywords
guanidine
composition
composition according
polymeric
vegetables
Prior art date
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Ceased
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PCT/AT2019/060098
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German (de)
English (en)
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Bcsk Biocid GmbH
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Bcsk Biocid GmbH
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Filing date
Publication date
Application filed by Bcsk Biocid GmbH filed Critical Bcsk Biocid GmbH
Publication of WO2019178632A1 publication Critical patent/WO2019178632A1/fr
Anticipated expiration legal-status Critical
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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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • A01N47/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
    • A01N47/44—Guanidine; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23B—PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
    • A23B2/00—Preservation of foods or foodstuffs, in general
    • A23B2/70—Preservation of foods or foodstuffs, in general by treatment with chemicals
    • A23B2/725—Preservation of foods or foodstuffs, in general by treatment with chemicals in the form of liquids or solids
    • A23B2/729—Organic compounds; Microorganisms; Enzymes
    • A23B2/762—Organic compounds containing nitrogen
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23B—PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
    • A23B7/00—Preservation of fruit or vegetables; Chemical ripening of fruit or vegetables
    • A23B7/14—Preserving or ripening with chemicals not covered by group A23B7/08 or A23B7/10
    • A23B7/153—Preserving or ripening with chemicals not covered by group A23B7/08 or A23B7/10 in the form of liquids or solids
    • A23B7/154—Organic compounds; Microorganisms; Enzymes
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23B—PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
    • A23B7/00—Preservation of fruit or vegetables; Chemical ripening of fruit or vegetables
    • A23B7/16—Coating with a protective layer; Compositions or apparatus therefor

Definitions

  • the invention relates to a liquid composition for increasing the shelf life of fruits and vegetables, comprising a polymeric guanidine.
  • Fruits and vegetables are especially important for a healthy diet. They contain a variety of important nutrients and trace elements. However, a supply of fresh fruit and vegetables is difficult, especially in winter.
  • Ethylene is a gaseous phytohormone that affects the maturation of fruits.
  • Fruits which release ethylene during storage are, for example, apples, apricots, avocados, pears, kaki fruits, kiwi, mango, melons, nectarines, papaya, peach, plums, tomatoes. This causes an acceleration of breathing, aging and maturation in many other species.
  • Fruits that are particularly susceptible to airborne ethylene, and therefore spoil significantly faster include eggplant, bananas, cauliflower, broccoli, chicory, peas, green beans, cucumbers, lettuce, pumpkins, carrots, peppers, parsley, Brussels sprouts, Watermelons.
  • Another key quality feature in fruits and vegetables is the taste. Storage often flattens the taste of fruits and vegetables and may cause an undesirable off-taste.
  • WO 2008/080184 describes the use of polymeric guanidines for controlling microorganisms.
  • EP 2 084 967 describes the treatment of banana trees. The polymeric guanidine is injected into the plant.
  • the object of the invention is therefore to provide an improved method for increasing the shelf life of harvested and intended for consumption fruits and vegetables.
  • composition according to claim 1 contains at least one polymeric guanidine, and at least one wetting agent dissolved in an inorganic solvent. It has surprisingly been found that the shelf life of fruits or vegetables intended for consumption is markedly improved by the composition according to the invention.
  • the Composition can be used to control unwanted microorganisms by exposing the surface of harvested fruits and vegetables.
  • Polymeric guanidines have a good activity against microorganisms.
  • the surface of the vegetable food can be completely treated. Only partial wetting or dripping of the composition is avoided. It thus forms a flat layer on the surface of the vegetable food.
  • the composition forms a film-forming layer on drying.
  • This layer consists of the polyaminosaccharide and the polymeric guanidine.
  • the polymeric guanidine remains attached to the surface of the vegetable food.
  • this layer is easily removable before consumption of the food by washing, for example, in water. This is especially important in plant foods whose shell is to be suitable for consumption. This may be the case when the fruit or vegetables are usually consumed with shell, such as apples or pears. Or even if the shell itself is used, such as the shell of citrus fruits when baking.
  • the application of the composition to the fruit or vegetables can be done, for example, by spraying, brushing or misting.
  • the misting is particularly suitable for use in containers, trailers, boxes and other transport containers.
  • Another possibility is that the fruit or vegetables are dipped in the composition and kept therein for a given residence time.
  • the residence time depends on the type of fruit or vegetable to be treated and is 1 to 5 minutes.
  • the fruit or vegetables can be removed from the solution and dried, for example, in the air.
  • the drying time depends on the climatic conditions.
  • Chitosan is particularly well suited.
  • Chitosan is a poly (D) glucosamine or a deacetyl chitin.
  • the degree of deacetylation is usually between about 60% and 100%.
  • a degree of deacetylation of 80% to 90% is particularly advantageous.
  • Chitosan has as natural product a particularly good compatibility. Even the consumption of chitosan is harmless according to today's findings.
  • the composition of the polymeric guanidine with chitosan as wetting agent is particularly suitable for use to increase the shelf life of fruits and vegetables.
  • the film-forming layer reduces the release of liquid from the stored plant foods. This can dehydration, and as a result, the shrinkage, be reduced. The stored fruits and vegetables will stay fresh longer.
  • the film-forming layer can also minimize the influence of ethylene on the harvested fruits and vegetables. This allows a common storage of different fruits, without having to accept limitations in durability.
  • this composition is particularly good washable with water. It has also surprisingly been found that washing not only the composition itself can be easily removed, but also common pesticides are washed off.
  • the composition of the polymeric guanidine with Chitosan thus serves as a solubilizer for common pesticides and increases their water solubility. As a result, fruit and vegetables treated with the composition are also cleaned of pesticide residues during washing.
  • water can be used as the solvent in the composition.
  • water By using water, a harmless in the food industry solvent can be used.
  • water is tasteless. Water evaporates without leaving residue and thus helps to form the protective layer.
  • water has particularly good dissolution properties for polymeric guanidines and polyaminosaccharides.
  • polymeric guanidines can be used for the composition.
  • the preparation of polymeric guanidines is described, for example, in WO 01/85676 A1 and in patents AT 408302 B and AT 411060 B.
  • Polymeric guanidines also include, for example, or are referred to as Akacid, or X-cid, and are described, for example, in Kratzer et al. , Antibiotics Monitor 1/2/2006; Buxbaum et al.
  • the polymeric guanidine may also be in the form of a complex, for example with gelatin or a polysaccharide (for example as described in WO 2010/106007 A1).
  • WO 2008/080184 describes the use of polymeric guanidines for controlling microorganisms in non-therapeutic applications, for example by nebulization for disinfecting the room.
  • a composition referred to therein is Akacid, poly [2- (2-ethoxy) -ethoxy-ethyl-guanidinium chloride and Akacid Plus, a 3: 1 mixture of poly (hexamethylene guanidinium chloride) and poly [2- (2-ethoxy ) ethoxyethyl) guanidinium chloride].
  • polymeric guanidines in particular for “polymeric guanidine derivatives based on an alkylenediamine and / or an oxyalkylenediamine” (WO 2009/009815 Al), especially for “polymeric guanidine derivatives based on diamines which alkyl chains and / or oxyalkylene chains between two Amino groups, the guanidine derivatives using a product of the polycondensation of a guanidine acid addition salt with diamines which contain polyalkylene chains and / or polyoxyalkylene chains between two amino groups.
  • EP 1 280 766 B1 claim 1.
  • guanidines Particularly preferred are a poly (hexamethyleneguanidinium ) Salt and / or poly [2- (2-ethoxy) ethoxyethyl] guanidinium salt
  • Akacid and Akacid Plus are preferred polymeric guanidines according to the present invention.
  • a preferred embodiment of the composition according to the invention is characterized in that a polymeric guanidine is provided which contains an alkylenediamine and the oxyalkylenediamine in a molar ratio between 4: 1 and 1: 4.
  • the amino groups of alkylenediamine and / or the Oxyalkylendiamins are preferably terminal, wherein for producing the polymeric guanidine as alkylenediamine a compound of general formula NH2 primarily (CH2) nN is provided H2, in which an integer between 2 and 10, in particular 6 , is.
  • a compound of the general formula NH 2 [( CH 2) 2 O)] m ( CH 2) 2 NH 2 may be provided as oxyalkylenediamine, in which an integer between 2 and 5, in particular 2.
  • Preferred polymeric guanidines may be selected from polyhexamethyleneguanidine; Poly [2- (2-ethoxy) ethoxyethyl] guanidine (Akacid, [374572-91-5]); Polytriethylenglykolguanidin; Polyethylenglykolguanidin; Polyoxypropylenguanidin; Polyoxyethylene guanidine or mixture of poly (hexamethyleneguanidinium chloride) and poly [2- (2-ethoxy) ethoxyethyl) guanidinium chloride] (Akacid Plus), especially a 3: 1 mixture.
  • the polymeric guanidine is a polyalkylene guanidine, especially a polyoxyalkylene guanidine.
  • Alkylene may be a C1-C8 alkyl, preferably a C2-C6 alkyl such as ethyl, propyl, butyl, methylpropyl, pentyl, branched or unbranched, which is preferred in all uses of the term “alkylene” or "alkyl” herein.
  • polyguanidine may correspond to the formula (I), (II) or (III)
  • Ri is either an aromatic ring system having at least one aromatic ring optionally containing one or more heteroatoms selected from O, N and S and which is optionally substituted with one or two vinyl groups, or is ethylene, or the one by ring closure
  • R 1 are benzenes (preferably para- or meta-digit embedded), pyridine (preferably attached to the two carbon atoms adjacent to the N), divinylbenzene, biphenyl (preferably both benzene linked in a para-position), 1, 3-bis ((E) -2-vinyl) benzene, furan, pyrrole, thiophene, fluorene, ethylene (preferably cis-linked).
  • Such polymeric guanidines are described in WO 2016/015081 A1.
  • Polymeric guanidines may also contain the compound of formula (IV)
  • Y is selected from -H and -R I -NH 2 ; or X and Y together represent a chemical bond to give a cyclic structure;
  • Ri is selected from divalent organic radicals having 2 to 20 carbon atoms in which one or more carbon atoms are optionally replaced by 0 or N; a and b are each 0 or 1,
  • R 2 is selected from -H and -NH 2 ,
  • n corresponds to a plurality, e.g. to achieve the above molar masses of the polymer.
  • n can be 3 to 200.
  • the guanidine is a guanidinium salt, preferably selected from a halide, preferably a chloride; Phosphate, preferably one
  • the polymeric guanidine of the present invention may be a polyguanidine salt.
  • salting partners e.g. Halide, phosphate, etc. are e.g. described in AT 411060 B.
  • the average molecular weight of the polymeric guanidine is 200 Da to 10,000 Da, preferably 500 Da to 3,000 Da.
  • the polymeric guanidine may be provided with at least 3 guanidine residues.
  • the polymers of these sizes can be obtained by nanofiltration through membranes become.
  • filters with corresponding pore sizes can be used for the permeability of the desired molecular weights. Filtrates (to remove larger polymers) or the residue (to remove the smaller polymers) can be further used to obtain the desired polymer.
  • the desired, preferred polymeric guanidines have improved toxicology.
  • compositions containing 0.025-0.4% by weight, in particular 0.04-0.15% by weight, of polymeric guanidine is particularly effective. Furthermore, it can be provided that the composition 0.5 to 5 wt.%.
  • Polyaminosaccharide in particular chitosan contains.
  • a good film-forming property can be achieved.
  • a particularly effective treatment can be achieved with a composition according to the following formulation.
  • Polymeric guanine 0.025-0.15% by weight
  • Fig. 1 shows oranges treated with an exemplary composition after storage
  • Fig. 2 shows untreated oranges which were stored simultaneously with the oranges of Fig. 3.
  • Fig. 3 shows apples treated with an exemplary composition after storage.
  • Fig. 4 shows untreated apples stored simultaneously with the apples of Fig. 1.
  • Example 1 Preparation of a polymeric guanidine (e.g., Akacid Plus)
  • the formulations are based on active ingredients of the group of polyguanidines (Akacid, described in Kratzer et al., Antibiotika Monitor 1/2/2006, Buxbaum et al., Journal of Antimicrobial Chemotherapy (2006) 58, 193-197, WO 01/85676
  • An exemplary composition was created by mixing the following components: Akacid Plus: 0.05 wt
  • Figures 1 and 2 show the effect of the exemplary composition on harvested oranges.
  • Fig. 1 shows the test group with 10 oranges
  • Fig. 2 shows the control group with also 10 oranges.
  • test group was treated after harvest with the exemplary composition (4000 ppm).
  • control group was not treated further.
  • Fig. 1 shows that in the test group, none of the oranges had a fungal infection.
  • Fig. 2 shows that in the control group all oranges showed a strong fungal attack. Seven oranges were completely covered by a fungus coating. The remaining three oranges were largely covered by a fungus layer.
  • Figures 3 and 4 show the effect of the exemplary composition on harvested apples.
  • Fig. 3 shows the test group with 10 apples
  • Fig. 2 shows the control group with also 10 apples.
  • the apples of both groups were vaccinated after harvest with Botrytis cinerea, the causative agent of apple disease.
  • the test group was additionally treated with the exemplary composition (2000 ppm).
  • the apples of the test group were optically indistinguishable from freshly harvested apples after storage for 10 days. In the control group, almost all apples were inedible.
  • the treated apples therefore had a significantly higher storage life.
  • the durability extension was tested by the use of exemplary solutions according to the invention of 10% Akacid Plus and chitosan in 2 varieties of Dangshan Su pear after harvest. Chitosan with a degree of deacetylation of 85% was used.
  • the aim was to determine the effect of the extension of the Shelf life with different concentrations of Akacid Plus 10% and chitosan.
  • Dangshan su pear pears were used.
  • the test material came from 10-year-old pear trees, which had no infestation with insects, microorganisms or other damage.
  • the pears were of largely the same maturity and size.
  • the average weight was 147.74 g, the average hardness was 2.79 kg / cm 2 and the average soluble solids content was 10.7.
  • the Dangshan Su pears were examined at normal room temperature compared to cold storage conditions.
  • the test conditions were five test arrangements for storage at room temperature and in cold storage conditions (0-2 C °).
  • the fruits of the test groups were initially held in the test solution for 5 minutes and then dried naturally for 24 hours. Each fruit was then stored on the bottom of a plastic drum (26 x 35 x 43 m) Closure was sealed with petroleum jelly. The fruits were stored under different temperature conditions.
  • Table 1 shows the evolution of strength during storage. The decrease in strength could be observed in all approaches, regardless of cool storage conditions or room temperature, or treatment with or without addition.
  • Table 2 shows the content of soluble solids. Soluble solids content in the pears was significantly greater at day 30 in the treated groups. Even under the cold storage conditions, a higher content was detectable. The different Akacid Plus concentrations of the compositions were associated with a 5% higher soluble solids content per stage. Table 2:
  • Tab. 3 shows the content of titratable acids.
  • titratable acid content there was a significant difference between the content of the pears treated with the test solution and the control group. The difference between room temperature and cold storage was not as pronounced as compared to the test group.
  • Table 5 shows the evaluation of the pears stored in cold storage conditions.
  • the used Akacid Plus - Chitosan mixture had a clear freshness effect on the pears. This was much more elaborate than the effect that could be achieved only by the cooler storage conditions.
  • the concentration that showed the best result in terms of freshness was a 500 ppm Akacid Plus dilution. It has been shown that treating the pears with an Akacid Plus chitosan solution has resulted in reduced aging, a better appearance and better inner quality of the pears.

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

Abstract

L'invention concerne une composition liquide contenant au moins une guanidine polymère ainsi qu'au moins un agent mouillant, dissous dans un solvant inorganique, ainsi que l'application de cette composition pour l'augmentation de la durée de conservation de fruits et légumes récoltés ou en tant que produit phytosanitaire contre les micro-organismes indésirables à la surface de fruits et légumes récoltés, ou un procédé d'augmentation de la durée de conservation de fruits et légumes récoltés ou de lutte contre des micro-organismes indésirables par application de cette composition à la surface de fruits et légumes récoltés.
PCT/AT2019/060098 2018-03-23 2019-03-22 Composition liquide contenant une guanidine polymère Ceased WO2019178632A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ATA50243/2018 2018-03-23
ATA50243/2018A AT521125A1 (de) 2018-03-23 2018-03-23 Flüssige Zusammensetzung

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WO2019178632A1 true WO2019178632A1 (fr) 2019-09-26

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Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2437844A1 (de) * 1973-08-06 1975-06-26 Ici Ltd Verfahren zur bekaempfung von schaedlingen
WO2005082178A1 (fr) * 2004-02-27 2005-09-09 Kalle Gmbh Enveloppe pour aliments comprenant des antimicrobicides
WO2008031105A1 (fr) * 2006-09-08 2008-03-13 Delaval Holdings Ab Germicides à base de sel d'un polymère de guanidine
EP2071954A1 (fr) * 2007-12-19 2009-06-24 Bayer CropScience AG Utilisation de dérivés de guanidine polymères destinés à combattre des microorganismes indésirables dans la protection des plantes
WO2012041910A1 (fr) * 2010-10-01 2012-04-05 Elektra Management S.R.O. Solution de composés de guanidinium, procédé utilisant ladite solution et utilisation associée
CN103976015A (zh) * 2014-05-13 2014-08-13 珠海真绿色技术有限公司 一种用于柑橘蒂腐病防治的含有聚氨丙基双胍的保鲜剂及其制备和应用
CN104170833A (zh) * 2014-09-02 2014-12-03 海南正业中农高科股份有限公司 含寡糖与聚六亚甲基双胍或其盐的组合物
CN105055642A (zh) * 2015-07-30 2015-11-18 上海宇昂新材料科技有限公司 一种复方胍类消毒剂及其制备方法
US20160029632A1 (en) * 2010-11-14 2016-02-04 South China Botanical Garden, Chinese Academy Of Sciences Citrus preservative of polyhexamethylene guanidine hydrochloride

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DE2437844A1 (de) * 1973-08-06 1975-06-26 Ici Ltd Verfahren zur bekaempfung von schaedlingen
WO2005082178A1 (fr) * 2004-02-27 2005-09-09 Kalle Gmbh Enveloppe pour aliments comprenant des antimicrobicides
WO2008031105A1 (fr) * 2006-09-08 2008-03-13 Delaval Holdings Ab Germicides à base de sel d'un polymère de guanidine
EP2071954A1 (fr) * 2007-12-19 2009-06-24 Bayer CropScience AG Utilisation de dérivés de guanidine polymères destinés à combattre des microorganismes indésirables dans la protection des plantes
WO2012041910A1 (fr) * 2010-10-01 2012-04-05 Elektra Management S.R.O. Solution de composés de guanidinium, procédé utilisant ladite solution et utilisation associée
US20160029632A1 (en) * 2010-11-14 2016-02-04 South China Botanical Garden, Chinese Academy Of Sciences Citrus preservative of polyhexamethylene guanidine hydrochloride
CN103976015A (zh) * 2014-05-13 2014-08-13 珠海真绿色技术有限公司 一种用于柑橘蒂腐病防治的含有聚氨丙基双胍的保鲜剂及其制备和应用
CN104170833A (zh) * 2014-09-02 2014-12-03 海南正业中农高科股份有限公司 含寡糖与聚六亚甲基双胍或其盐的组合物
CN105055642A (zh) * 2015-07-30 2015-11-18 上海宇昂新材料科技有限公司 一种复方胍类消毒剂及其制备方法

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YAGE XING ET AL: "Chitosan-Based Coating with Antimicrobial Agents: Preparation, Property, Mechanism, and Application Effectiveness on Fruits and Vegetables", INTERNATIONAL JOURNAL OF POLYMER SCIENCE, vol. 2016, 1 January 2016 (2016-01-01), pages 1 - 24, XP055592938, ISSN: 1687-9422, DOI: 10.1155/2016/4851730 *

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