AU1508800A - Post-harvest method for treating fruits and vegetables using eugenol and/or isoeugenol - Google Patents

Post-harvest method for treating fruits and vegetables using eugenol and/or isoeugenol Download PDF

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AU1508800A
AU1508800A AU15088/00A AU1508800A AU1508800A AU 1508800 A AU1508800 A AU 1508800A AU 15088/00 A AU15088/00 A AU 15088/00A AU 1508800 A AU1508800 A AU 1508800A AU 1508800 A AU1508800 A AU 1508800A
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eugenol
weight
process according
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vegetables
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Gilbert Bompeix
Alberto Sardo
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Xeda International SA
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Xeda International SA
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    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N65/00Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • A01N65/08Magnoliopsida [dicotyledons]
    • A01N65/38Solanaceae [Potato family], e.g. nightshade, tomato, tobacco or chilli pepper
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N31/00Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/08Oxygen or sulfur directly attached to an aromatic ring system
    • A01N31/16Oxygen or sulfur directly attached to an aromatic ring system with two or more oxygen or sulfur atoms directly attached to the same aromatic ring system
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N65/00Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N65/00Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • A01N65/06Coniferophyta [gymnosperms], e.g. cypress
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N65/00Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • A01N65/08Magnoliopsida [dicotyledons]
    • A01N65/28Myrtaceae [Myrtle family], e.g. teatree or clove
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N65/00Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • A01N65/08Magnoliopsida [dicotyledons]
    • A01N65/34Rosaceae [Rose family], e.g. strawberry, hawthorn, plum, cherry, peach, apricot or almond
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23BPRESERVING, e.g. BY CANNING, MEAT, FISH, EGGS, FRUIT, VEGETABLES, EDIBLE SEEDS; CHEMICAL RIPENING OF FRUIT OR VEGETABLES; THE PRESERVED, RIPENED, OR CANNED PRODUCTS
    • A23B7/00Preservation or chemical ripening of fruit or vegetables
    • A23B7/14Preserving or ripening with chemicals not covered by groups A23B7/08 or A23B7/10
    • A23B7/153Preserving or ripening with chemicals not covered by groups A23B7/08 or A23B7/10 in the form of liquids or solids
    • A23B7/154Organic compounds; Microorganisms; Enzymes

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  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Agronomy & Crop Science (AREA)
  • Microbiology (AREA)
  • Plant Pathology (AREA)
  • Dentistry (AREA)
  • Environmental Sciences (AREA)
  • Biotechnology (AREA)
  • Mycology (AREA)
  • Chemical & Material Sciences (AREA)
  • Botany (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Pest Control & Pesticides (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Cultivation Of Plants (AREA)
  • Storage Of Fruits Or Vegetables (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Epoxy Compounds (AREA)

Abstract

The invention concerns an anti-germinating method for tubers and bulbs consisting in applying on said tubers and bulbs a treatment composition based on an active principle selected among eugenol, a eugenol salt fit for human consumption, isoeugenol, an isoeugenol salt fit for human consumption and their mixtures. The invention also concerns the use of a composition based on an active principle selected among eugenol, a eugenol salt fit for human consumption, isoeugenol, an isoeugenol salt fit for human consumption and their mixtures as anti-germinating agent.

Description

WO 00/32053 PCT/FR99/03007 Process for treating fruit and vegetables after harvesting using eugenol and/or isoeugenol The invention relates to a process for treating 5 fruit and vegetables after harvesting, by applying a treating composition based on eugenol or isoeugenol to the said fruit and vegetables. It is important for fruit and vegetables not to loose their organoleptic quality and to conserve an 10 appealing appearance when they are placed on sale, for rapid consumption. However, after harvesting, fruit and vegetables are commonly stored for relatively long periods before being placed on sale. 15 The phenomena likely to impair the appearance and taste of fruit and vegetables are, in particular, the proliferation of fungi and bacteria on their surface. These degradations are even faster in the region of the small bruises and nicks appearing on the 20 skin of fruit and vegetables during their storage or handling. Many processes exist in the prior art for treating fruit and vegetable to enable the proliferation of bacteria and fungi at the surface of 25 the fruit and vegetables to be slowed down and/or partially or totally prevented. The active principles used in most of these processes are synthetic products, which present high risks of toxicity for the consumer, as a result of 30 which the permitted doses are always low. Consequently, research efforts have essentially been directed towards the development of ever more effective products. The development of these treating agents is very expensive, to the detriment of the economic 35 viability of the treatment. To overcome these drawbacks, processes using natural products have been proposed.
- 2 Thus, patent application FR 95/05157 is directed towards an antifungal treatment process for fruit and vegetables which consists in applying a terpene-based composition to the said fruit and 5 vegetables. The example in that document more specifically illustrates a treating composition based on L-carvone. More generally, that document makes reference to the use of monooxygenated terpenes such as terpineol, menthol, menthone, cineol (or eucalyptol) 10 and citronellal. However, these natural products are less effective than many of the synthetic products developed to date. The invention is based on the discovery of the 15 unexpected efficacy of two dioxygenated terpenes, i.e. eugenol and isoeugenol, of formulae: OH OH OCH3
OCH
3
CH
2
-CH=CH
2
CH=CH-CH
3 Eugenol Isoeugenol 20 in protecting fruit and vegetables against bacteria and fungi. One of the particularly advantageous characteristics of eugenol and isoeugenol is their 25 broad spectrum of activity: in fact, the superiority of these substances over other terpenes is manifested in the case of very varied bacterial strains and in the case of very varied species of fungi. Amongst the bacterial strains are, for example, 30 Erwinia carotovora or Escherichia coli. Examples of fungal species which may be mentioned are Fusarium oxysporum, Geotrichum candidum, Gloeosporium fructigenum, Penicillium digitatum, Penicillium expansum and Phytophthora parasitica.
- 3 The invention thus relates to a process for treating fruit and vegetables after harvesting, characterized in that it comprises the steps consisting in: 5 a - bringing a treating composition to a temperature of 400C to 60 0 C, b - subjecting the said fruit and vegetables to a treatment, for not more than 10 minutes, by spraying them with the said treating composition or by immersing 10 them in the said treating composition, and doing so before storing the fruit and vegetables, the said treating composition comprising, as percentages by weight: - from 10% to 40% of an active principle chosen 15 from eugenol, a nutritionally acceptable eugenol salt, isoeugenol, a nutritionally acceptable isoeugenol salt, and mixtures thereof; - from 0% to 90% of a nonionic surfactant; and 20 - from 0% to 90% of a solvent chosen from aliphatic alcohols, glycols, water and alkyl esters of carboxylic acids, and mixtures thereof; the treatment of tubers and bulbs being excluded. 25 In step a), the temperature to which the treating composition is heated is adjusted depending on the nature of the product treated. In fact, it is important not to cause the fruit and vegetables to cook or degrade. Only the surface of the fruit and 30 vegetables should be heated by placing in contact with the treating composition. According to one preferred embodiment, the surface should reach at least 35*C, better still at least 400C, for example between 450C and 500C. 35 In general, the treating composition is brought to a temperature of between 40'C and 600C and the contact time is adjusted in parallel so as to reach the desired temperature at the surface of the fruit and vegetables.
The treating composition is preferably brought to between 450C and 55 0 C, better still between 480C and 520C, for example 500C. In step b), the contact time is very short and 5 in all cases less than 10 minutes. It generally ranges between 30 seconds and 10 minutes, advantageously between 30 seconds and 5 minutes. A contact time of 2 to 3 minutes is usually sufficient. When the duration of treatment with the hot 10 composition has passed, the application is stopped by any known means, in particular by simply stopping the sprinkling or spraying. In one advantageous variant, in particular in the case of heat-sensitive fruit and vegetables, the 15 process can comprise a further step consisting in rapidly cooling the fruit or vegetables which have been placed in contact with the hot treating composition, cooling them down to a temperature below or equal to ambient temperature. 20 This cooling can be carried out by circulation of air or by contact with water (in particular immersion or spraying), the temperature of which is below or equal to ambient temperature. In the case of fruit and vegetables that are 25 particularly heat-sensitive, such as peaches, apricots, tomatoes and pears, it is recommended to cool them before carrying out the hot treatment with the said treating composition. The cooling should take effect down to the very core of the fruit and vegetables. The 30 fruit and vegetables are, for example, subjected to a treatment by hydrocooling. This can be carried out by spraying them with an aqueous cooling composition or by immersing them in an aqueous cooling composition. The temperature of the aqueous cooling 35 composition is generally between 00C and 150C. The temperature and time of pretreatment with the cooling composition are adjusted so as to cool the treated fruit or vegetables entirely rather than just their outer layer. These parameters depend mainly on - 5 the nature of the fruit and vegetables. As a guide, it will be noted that the temperature of the cooling composition is less than or equal to the conventional storage temperature recommended in the art. 5 According to one preferred embodiment, the aqueous cooling composition has a temperature of from 00C to 10 0 C, better still from 00C to 5-60C. The duration of the pretreatment with the aqueous cooling composition is generally between 2 minutes and 2 hours, 10 usually between 2 minutes and 60 minutes, for example between 4 minutes and 30 minutes. This variant is described more specifically in patent applications FR 96/03100 and FR 98/08995. The active principle can comprise a 15 nutritionally acceptable eugenol or isoeugenol salt. Salts that are particularly preferred include, in particular, alkali metal salts such as the sodium salts, lithium salts and potassium salts. According to a first embodiment of the 20 invention, the active principle is preferably a nutritionally acceptable salt or a mixture of such salts. Specifically, in this case, lower volatility of the active principle is observed. In this way, the duration of protection of the fruit and vegetables 25 after the treating composition has been applied is prolonged. The active principle advantageously comprises one or more nutritionally acceptable eugenol salts. According to a second embodiment of the 30 invention, the active principle is chosen from eugenol, nutritionally acceptable eugenol salts, and mixtures thereof. It should be understood that the treating composition can comprise, in addition to the active 35 principle of eugenol or isoeugenol type, another active principle which counteracts the growth of bacteria and fungi and/or which inhibits the germination of potatoes and onions.
- 6 Examples of nonionic surfactants which can be used according to the invention include, in particular: - the product of condensation of an aliphatic fatty alcohol, which is preferably C8-C22, with a C2-C3 5 alkylene oxide. The C 2
-C
3 alkylene oxide can be ethylene oxide, propylene oxide or a mixture of ethylene oxide and propylene oxide in any proportion. An example of such surfactants is the product of condensation of lauryl alcohol (or n-dodecyl alcohol) with 30 mol of 10 ethylene oxide; - the product of condensation of an alkylphenol in which the alkyl chain is C8-C22 with a C2-C3 alkylene oxide. In this case also, the products of condensation with ethylene oxide, propylene oxide or a mixture of 15 ethylene oxide and propylene oxide in any proportion are also advantageous. As an example of such surfactants, mention may be made of the product of condensation of n-nonylphenol with 10 mol of ethylene oxide; 20 - the product of condensation of a fatty acid, which is preferably C8-C22, with a C2-C3 alkylene oxide, for example ethylene oxide or propylene oxide or a mixture of ethylene oxide and propylene oxide in any proportion. These condensation products have an 25 alkoxylated chain on the hydroxyl function of the carboxylic group. Preferred surfactants of this group are the condensation products obtained from ricinoleic acid with 10 mol of ethylene oxide. It should be understood that -the surfactant can 30 consist of several nonionic surfactants. When the treating composition comprises active substances in the form of salts, the presence of a surfactant is optional. This surfactant is then generally present in the treating composition in a 35 proportion of from 0% to 20% by weight, for example from 10% to 20% by weight. When the treating composition comprises only salified active substances, the surfactant can represent from 10% to 90% by weight and preferably from 15% to 85% by weight of the composition, for example from 10% to 20% by weight. Examples of preferred aliphatic alcohols include C 1
-C
1 2 alkanols. 5 In the context of the invention, glycols denote alkylene glycols and polyalkylene glycols. The term "alkylene glycol" means dihydroxylated alcohols derived from aliphatic hydrocarbons by replacing two hydrogen atoms with two hydroxyl groups. 10 (C2-C6)alkylene glycols such as ethylene glycol and propylene glycol are preferred. The term "polyalkylene glycol" means the compounds of formula HO- (CpH 2 pO)n-H 15 in which p and n are integers between 2 and 6. By way of example, mention may be made of dipropylene glycol. According to the invention, the group CpH 2 pO is linear or branched. The preferred polyalkylene glycol 20 according to the invention is dipropylene glycol. The preferred alkyl esters of carboxylic acids are the (Cl-C6)alkyl esters of (C 1
-C
6 ) alkanoic acid, such as butyl acetate. Water is a preferred solvent. 25 It should be understood that the solvent can consist of a mixture of solvents. When the treating composition comprises active substances in the form of salts, the presence of a solvent is highly desirable. Tha solvent will 30 preferably represent from 40% to 90% by weight of the composition, for example from 50% to 85% by weight, better still from 50% to 80% by weight and generally from 60% to 80% by weight. The solvent in this case is advantageously water. 35 When the treating composition does not comprise only salified active substances, the amount of solvent may be smaller. It may advantageously range between 0% and 80% by weight, better still between 0% and 50% by weight, for example between 0% and 20% by weight.
- 8 According to another preferred embodiment, one or more agents for reducing the evaporation of the active principle are added to the treating composition. Such agents are known in the art. 5 By way of example, mention may be made of water-dispersible polyterpenes; glycerol esters of pine resin; gum lacquers; lecithins; drying oils; polyvinyl alcohol; polyvinylpyrrolidone; alkali metal polyacrylates; and gum arabic. 10 Isoprene polymers and natural rubber are polyterpenes which can be used in the context of the invention. The glycerol esters of pine resin are abietic acid esters. 15 The gum lacquers can be used in their natural form or in purified form, such as shellac resin. The lecithins are mixtures of combinations of oleic, stearic and palmitic acid esters with glycerophosphoric acid and choline. 20 The polyvinyl alcohol, polyvinylpyrrolidone, alkali metal polyacrylates and gum arabic are water soluble synthetic resins which also function as agents for reducing the evaporation of the active principle. However, it should be understood that the 25 invention is not in any way limited to the use of these specific water-soluble resins, but that any other type of water-soluble resin may also be suitable provided that it is capable of reducing the evaporation of the active principle. 30 Preferred examples of drying oils are glyceryl linoleate, linoleic acid and linolenic acid. When it is present, the evaporation-reducing agent represents from 0% to 10% by weight and preferably between 1% and 10% by weight of the treating 35 composition. One preferred formulation of the treating composition is as follows: - 15% to 30% by weight of active principle, better still from 15% to 25% by weight; - 9 - 0% to 20% by weight of a nonionic surfactant, better still from 10% to 20% by weight; - 40% to 90% by weight of a solvent (preferably water), better still from 50% to 80% by weight. 5 In this case, it is advantageous to use active principles in the form of salts. Another preferred formulation is as follows: - from 15% to 30% by weight of active principle, better still from 15% to 25% by weight; 10 - from 10% to 85% by weight of nonionic surfactant, better still from 15% to 85% by weight; - from 0% to 50% by weight of solvent, better still from 0% to 20% by weight. In this case, it is advantageous to use non 15 salified active principles. The treating composition is prepared in a conventional manner per se by simply mixing its constituents together. When the treating composition comprises a 20 nutritionally acceptable salt, this salt may be introduced into the composition, during its preparation, in salt form or else in neutral form; in the latter case, the salt is formed in situ by addition of a suitable base such as an alkali metal hydroxide 25 (sodium hydroxide or potassium hydroxide). The amount of treating composition which needs to be applied to the fruit and vegetables depends on the nature of the fruit and vegetables concerned and on the application method selected. 30 The residual amount of active principle remaining on the fruit and vegetables after application generally varies after each application between 0.4 g and 20 g per tonne of fruit or vegetables treated. More generally, the amount of active principle 35 applied will be adjusted as a function of the duration of storage. Since eugenol and isoeugenol are odoriferous products, it is in fact preferable that, at the end of storage, most of the active principle should have evaporated off so as not to adversely affect the - 10 commercial value of the fruit and vegetables when they are placed on sale. The amount of active principle which needs to be applied thus depends on the volatility of the active principle and on the duration 5 of storage. The process of the invention is particularly advantageous since it uses an active principle which is particularly effective as a bactericide and fungicide. The implementation variants specifically 10 described above are themselves also particularly advantageous since they contribute towards improving the efficacy of the active principle: - by increasing the penetration of the active principle into the surface layer of the fruit and 15 vegetables; - due to the introduction into the treating composition of agents which reduce the volatility of the active principle; - due to the use of a nutritionally acceptable 20 salt of eugenol and/or isoeugenol. The treatment of tubers (and, for example, of potato tubers) and that of bulbs (such as onion bulbs) is excluded from the context of the invention. The examples which follow further illustrate 25 the invention. EXAMPLE 1 This example illustrates aqueous compositions which can be used in unmodified form-in the process of 30 the invention. The active principle in these aqueous compositions is eugenol in the form of its sodium salt. Table 1 gives the formulation of compositions 1.1 to 1.3.
- 11 TABLE 1 EXAMPLE SURFACTANT EUGENOL NaOH Water 1.1 0 15 8 77 1.2 15 16 4 65 1.3 0 14 2.4 83.6 Table 1 gives the weight percentages of the 5 various constituents. EXAMPLE 2 The fungicidal activity of eugenol and isoeugenol was demonstrated in vitro and compared with 10 that of other terpenes. The cristomalt medium used to evaluate the fungicidal activities contains 0.1% cristomalt (malt extract) and 0.2% agar agar. After sterilization, this culture medium is 15 brought to 550C. The terpene compound tested is then introduced in pure form into the hot culture medium. Immediately after stirring, the medium supplemented with the terpene product is poured into Petri dishes (9 cm diameter, filled with 20 ml of medium) . The agar 20 medium solidifies on cooling. The Petri dishes are then inoculated with explantates (plugs) 6 mm in diameter taken from the edge of a culture of the test fungus obtained on cristomalt medium. The inoculation is carried out at 220C. 25 The mycelial growth was determined periodically (5 to 15 days depending on the species of fungus). The results are expressed in Table 3 below in terms of MIC, which is the content (in ptg/ml) which gives total inhibition of mycelial growth. 30 It will be noted that ranges of variation of the MIC values are indicated in Table 2. In fact, each experiment was carried out several times such that, for each terpene and for each species of fungus, a minimum value and a maximum value were obtained. 35 - 12 TABLE 2 CARVONE EUCALYPTOL EUGENOL ISOEUGENOL TERPINEOL SAFROL AA 40-80 >1280 20-40 20-40 40-80 80-160 BC 20-40 640-1280 20-40 20-40 40-80 80-160 FO 40-80 640-1280 20-40 20-40 40-80 80-160 GC 80-160 320-640 10-20 10-20 80-160 160-230 GR 40-80 320-640 20-40 20-40 40-80 40-80 PD 40-80 >1280 20-40 20-40 40-80 160-230 PE 80-160 >1280 20-40 20-40 40-80 640-1280 PV 80-160 160-320 40-80 20-40 40-80 80-160 PhP 40-80 320-640 20-40 20-40 20-40 40-80 Throughout the text of the present description, 5 the meanings of the abbreviations used in Table 2 are as follows: AA Alternaria alternata BC Botrytis cinerea FO Fusarium oxysporum 10 GC Geotrichum candidum GR Gliocladium roseum PD Penicillium digitatum PE Penicillium expansum PV Phlyctaena vagabonda ("Gloeosporium") 15 PhP Phytophthora parasitica The analysis of the results obtained is carried out simply by using the assessment scale illustrated in Table 3: 20 - 13 TABLE 3 MIC included in the range Grades of inhibition delimited by the two values indicated in ppm (g/ml) 10-20 8 (strong inhibition) 20-40 7 40-80 6 80-160 5 160-320 4 320-640 3 640-1280 2 >1280 1 (weak inhibition) In Table 4, the results obtained have been 5 expressed using the scale from Table 3. TABLE 4 CARVONE EUCALYPTOL EUGENOL ISOEUGENOL TERPINEOL SAFROL AA 6 1 7 7 6 5 BC 7 2 7 7 6 5 FO 6 2 7 7 6 5 GC 5 3 8 8 5 4 GR 6 3 7 7 6 6 PD 6 1 7 7 6 4 PE 5 1 7 7 6 2 PV 5 4 6 7 6 5 PhP 6 3 7 7 7 6 Total of the 52 20 63 64 54 42 degrees of in hibition 10 It emerges clearly from Table 4 that eugenol and isoeugenol are markedly more active than the other terpenes.
- 14 EXAMPLE 3 The activity of eugenol and isoeugenol on spore germination was evaluated in vitro and compared with that of other terpenes. 5 The procedure of Example 2 was used to do this, except that the concentration of eugenol and isoeugenol was set at x pg/ml in the culture media used and that 50 ptl of a spore suspension adjusted to 100,000 spores/ml are placed in each Petri dish. 10 The same experiment was carried out starting with a terpene-free culture medium (control test). The results were evaluated using the following assessment criteria: ++ : spore germination comparable to that of the 15 control + : considerable reduction in the level of spores germinated 0 : no spores germinated. Tables 5, 6 and 7 show the results obtained for 20 3 different concentrations of terpenes in the culture medium, i.e. 40 ptg/ml, 80 pg/ml and 1280 ig/ml. TABLE 5 (x = 40 pg/ml) CARVONE EUCALYPTOL EUGENOL ISOEUGENOL TERPINEOL SAFROL AA + ++ 0 0 ++ ++ BC + ++ 0 ++ + + FO + ++ 0 0 ++ ++ GC + ++ 0 0 ++ ++ PD + + 0 0 ++ + PE + + 0 0 ++ + PV + ++ 0 0 ++ + PhP 0 ++ 0 0 + 0 25 - 15 TABLE 6 (x = 80 ptg/ml) CARVONE EUCALYPTOL EUGENOL ISOEUGENOL TERPINEOL SAFROL AA 0 ++ 0 0 0 + BC 0 ++ 0 0 0 0 FO 0 ++ 0 0 0 + GC 0 + 0 0 + + PD 0 + 0 0 0 + PE 0 + 0 0 + + PV 0 + 0 0 0 + PhP 0 + 0 0 0 0 5 TABLE 7 (x = 1280 pg/ml) CARVONE EUCALYPTOL EUGENOL ISOEUGENOL TERPINEOL SAFROL AA 0 0 0 0 0 0 BC 0 0 0 0 0 0 FO 0 0 0 0 0 0 GC 0 0 0 0 0 0 PD 0 + 0 0 0 0 PE 0 + 0 0 0 + PV 0 0 0 0 0 0 PhP 0 0 0 0 0 0 It results clearly from these various tables that the activity of eugenol and isoeugenol is far 10 superior to that of the other terpenes. A concentration of 40 ptg/ml is sufficient to inhibit spore germination. EXAMPLE 4 The bactericidal activity of eugenol and 15 isoeugenol was evaluated in vitro and compared with that of other terpenes. The culture medium used is the following LB medium: Bactotryptone: 1% by weight 20 Yeast extract: 0.5% by weight - 16 NaCl: 0.5% by weight Agar agar: 1.2% by weight A bacterial suspension containing 106 CFU/ml was prepared in sterilized water using the LB medium. 5 200 pl of this bacterial suspension were added to 20 ml of presterilized LB culture medium and brought to 55*C. The terpene tested is then added to the culture medium. After stirring, the medium is immediately distributed in Petri dishes. The medium solidifies on cooling. 10 The incubation is carried out at 28 0 C when the bacterium is Erwinia carotovora and at 37 0 C when the bacterium is Escherichia coli. The growth of the bacterial cloud in the culture medium is observed. The same experiment is 15 carried out in the absence of terpene (control experiment). The results are evaluated using the following assessment scale: ++ : bacterial cloud identical to that of the control 20 + : bacterial cloud present with a marked reduction in growth relative to the control : total absence of growth. Table 8 summarizes the results obtained for 3 different concentrations, i.e. 20, 80 and 320 pg/ml in 25 the case of the bacterium Erwinia carotovora. TABLE 8 Concen CARVONE EUCALYPTOL EUGENOL ISOEUGENOL TERPINEOL SAFROLE in pg/m1 20 ++ ++ + + ++ ++ 80 + ++ - - + ++ 320 - ++ - - - + 30 In another series of experiments, the concentration of terpene required for total inhibition of the growth of the bacteria (MIC) was determined. The - 17 procedure used is that described above. The results obtained are given in Table 9 below. TABLE 9 5 MIC in CARVONE EUCALYPTOL EUGENOL ISOEUGENOL TERPINEOL SAFROL pg/ml Erwinia 80-160 320-640 20-40 20-40 80-160 320-640 sp. Esche- 320-640 >640 40-80 40-80 160-320 >640 richia On the two bacteria, eugenol and isoeugenol are found to be the most active.

Claims (12)

1. Process for treating fruit and vegetables after harvesting, characterized in that it comprises the 5 steps consisting in: a - bringing a treating composition to a temperature of 400C to 600C, b - subjecting the said fruit and vegetables to a treatment, for not more than 10 minutes, by spraying 10 them with the said treating composition or by immersing them in the said treating composition, and doing so before storing the fruit and vegetables, the said treating composition comprising, as percentages by weight: 15 - from 10% to 40% of an active principle chosen from eugenol, a nutritionally acceptable eugenol salt, isoeugenol, a nutritionally acceptable isoeugenol salt, and mixtures thereof; 20 - from 0% to 90% of a nonionic surfactant; and - from 0% to 90% of a solvent chosen from aliphatic alcohols, glycols, water and alkyl esters of carboxylic acids, and mixtures thereof; 25 the treatment of tubers and bulbs being excluded.
2. Treatment process according to Claim 1, characterized in that, before treating the fruit and vegetables with the said treating composition, they are cooled to the core by spraying with an aqueous cooling 30 composition or by immersion in an aqueous cooling composition, the said aqueous cooling composition having a temperature of greater than or equal to OC and less than or equal to 150C.
3. Treatment process according to either of the 35 preceding claims, characterized in that the said active principle is a nutritionally acceptable salt or a mixture of such salts. - 19
4. Process according to any one of the preceding claims, characterized in that the active principle is eugenol, a nutritionally acceptable eugenol salt or a mixture thereof.
5 5. Process according to any one of the preceding claims, characterized in that the said treating composition also comprises one or more agents for reducing the evaporation of the said active principle.
6. Treatment process according to Claim 4, 10 characterized in that the evaporation-reducing agents are chosen from water-dispersible polyterpenes; glycerol esters of pine resin; gum lacquers; lecithins; drying oils; polyvinyl alcohol; polyvinylpyrrolidone; alkali metal polyacrylates; and gum arabic. 15
7. Process according to either of Claims 5 and 6, characterized in that the said treating composition comprises from 1% to 10% by weight of one or more evaporation-reducing agents.
8. Process according to any one of the preceding 20 claims, characterized in that the said treating composition is brought to a temperature of 45 0 C to 50 0 C in step (a).
9. Process according to any one of the preceding claims, characterized in that the said treating 25 composition essentially comprises: - from 15% to 30% by weight of active principle; - from 0% to 20% by weight of nonionic surfactant; 30 - from 40% to 90% by weight of a solvent.
10. Process according to Claim 9, characterized in that the solvent is water and the active principle is a salt or a mixture of salts.
11. Process according to any one of Claims 1 to 8, 35 characterized in that the treating composition essentially comprises: - from 15% to 30% by weight of active principle; - 20 - from 15% to 85% by weight of nonionic surfactant; - from 0% to 50% by weight of solvent.
12. Process according to Claim 11, characterized in 5 that the active principle is chosen from eugenol and isoeugenol, and mixtures thereof.
AU15088/00A 1998-12-03 1999-12-03 Post-harvest method for treating fruits and vegetables using eugenol and/or isoeugenol Ceased AU769891B2 (en)

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FR98/15305 1998-12-03
PCT/FR1999/003007 WO2000032053A1 (en) 1998-12-03 1999-12-03 Post-harvest method for treating fruits and vegetables using eugenol and/or isoeugenol

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DE69915033T2 (en) 2004-12-30
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