PLANT PROTECTION METHOD USING CARYOPHYLLENE

Caryophyllene, used as an adjuvant in plant protection treatments, addresses terpene-induced phytotoxicity by reducing damage and enhancing treatment efficacy, enabling higher doses and safer plant protection.

FR3162116A1Pending Publication Date: 2025-11-21XEDA INTERNATIONAL SA
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Patent Information

Application Number
FR2024004924
Authority / Receiving Office
FR · FR
Patent Type
Applications
Current Assignee / Owner
Filing Date
2024-05-14
Publication Date
2025-11-21

AI Technical Summary

Technical Problem

Terpenes used in plant protection products exhibit phytotoxicity, limiting their application doses and affecting the integrity of treated plants, necessitating a method to increase treatment effectiveness while maintaining plant integrity and ensuring food safety.

Method used

The use of caryophyllene as an adjuvant in plant protection treatments, applied simultaneously or separately, at a ratio of 2/8 to 9/1 by weight with the plant protection product, to mitigate phytotoxicity and enhance treatment efficacy.

Benefits of technology

Caryophyllene effectively reduces phytotoxicity, allowing higher application doses of terpenes and improving the effectiveness of plant protection treatments without harming the treated plants.

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Abstract

PLANT PROTECTION PROCESS USING CARYOPHYLLENE This application relates to a plant protection treatment process using caryophyllene, in which caryophyllene has a protective action against the aggressiveness of the plant protection treatment. Figure for abstract: None
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Description

Title of the invention: PROCESS FOR PLANT HEALTH TREATMENT USING CARYOPHYLLENE

[0001] The present invention relates to the protection of plants subjected to phytosanitary treatment, and in particular to phytosanitary treatments based on terpenes. It finds particular application in the field of plant treatment using products of natural origin.

[0002] Terpenes and the essential oils containing them are considered effective alternatives to synthetic plant protection products. For example, the Bioxeda® composition containing clove oil is marketed for fungicide treatment, and Biox-M® is a germination inhibitor based on spearmint oil.

[0003] However, terpenes exhibit phytotoxicity towards treated plants, which therefore limits the application doses.

[0004] For example, clove oil can be aggressive on citrus peel at doses of around 1000 ppm.

[0005] It would be desirable to ensure the maintenance of the integrity of the treated plants in order to be able to increase the application doses of plant protection products in order to increase the effectiveness of the treatments.

[0006] It is therefore particularly desirable to make available a method for protecting plants, especially fruits and vegetables, against the aggressive effects of plant protection treatments. The treatment must be as harmless as possible to the plant being treated, acceptable from a food standpoint, and easy and economical to implement. Furthermore, it is important to provide a treatment with a limited phytotoxic effect and of natural origin for better food compatibility.

[0007] Caryophyllene is a sesquiterpene found in many essential oils. Its use is authorized under REACH regulations. It exhibits cannabinoid (type 2) activity without psychomimetic effects (CB1). It has numerous therapeutic effects.

[0008] FR3127367 describes the nematicidal activity of caryophyllene and its low phytotoxicity compared to other terpenes. However, its effect of reducing or inhibiting the aggressiveness of other terpenes is not suggested.

[0009] The Applicant has now discovered unexpected properties of caryophyllene: It exhibits, against all expectations, a protective activity against the aggressiveness of plant protection treatments, particularly those based on terpenes.

[0010] According to a first object, the present invention relates to a method for protecting plants against the phytotoxicity of treatment with a plant protection product, said method comprising the addition of caryophyllene to the plant protection treatment,

[0011] the application of the plant protection product and caryophyllene can be simultaneous or separate,

[0012] said process being characterized in that the caryophyllene / plant protection product ratio is between 2 / 8 and 9 / 1 by weight.

[0013] The following features, or each of their combinations, represent preferred embodiments of the process according to the invention:

[0014] The term "caryophyllene" used here refers to [3-caryophyllene (also trans-caryophyllene, CAS 87-44-5) with IUPAC nomenclature 17?,47?,95)-4,11,1 l-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene and corresponding to the general formula:

[0015] And / or

[0016] α-caryophyllene (also called humulene, CAS 6753-98-6) of nomenclature IUPAC (1^,4^,8^)-2,6,6,9-tetramethylcycloundeca-1,4,8-triene and corresponding to the general formula:

[0017] These two isomers of caryophyllene can be present in mixture in aromatic plants.

[0018] Thus, according to one embodiment, the term "caryophyllene" refers to each of the two isomers, as well as mixtures of α-caryophyllene and [3-caryophyllene.

[0019] According to the invention, "phytotoxicity" or "aggressiveness" means any damage to fruits and vegetables resulting from the direct action of the phytosanitary treatment, illustrated in particular by the modification of the visual appearance of said fruits and vegetables or their leaves.

[0020] Preferably, according to the invention, "phytotoxicity" therefore refers to the direct alteration, by phytosanitary treatment, of the integrity of the skin of said fruits and vegetables, in particular by modification of the color or texture of their skin. More specifically, phytotoxicity can be illustrated by a homogeneous yellowish coloration, a reddish pigmentation, the formation of yellow or brown spots or areas of necrosis, localized or widespread, or even the formation of microlesions on the skin.

[0021] These micro-lesions then constitute a favorable environment for mold or rotting of fruits and vegetables.

[0022] According to the invention, the phytotoxicity defined above results directly from the action of one or more plant protection products applied by the plant protection treatment and therefore excludes natural aging phenomena, such as senescence in particular.

[0023] As used here, the term "plant protection treatment" refers to the treatment of cultivated or harvested plants against insects and pests and diseases, and / or more broadly to the improvement of yields. According to the invention, plant protection treatment is characterized in particular by insecticidal, fungicidal, bactericidal or nematicid, biostimulant, or nutritional activity. Treatment is understood here to mean any action enabling the prevention of a future infestation or the eradication of an existing infestation.

[0024] More specifically, the said phytosanitary treatment refers to the active substance(s) applied, designated herein as phytosanitary product.

[0025] Said plant protection product may be chosen in particular from among the active ingredients of a plant protection treatment having a harmful phytotoxic effect, especially at its effective dose. It may be chosen from among insecticides, fungicides, bactericides, nematicides, biostimulants, fertilizers, feed additives used in the field and / or post-harvest, whether of natural or synthetic origin.

[0026] According to one embodiment, the phytosanitary treatment includes the application of one or more terpenes as a phytosanitary product, and will hereafter be referred to as "terpene treatment".

[0027] According to one embodiment, the plant protection product can be chosen from among the terpene(s), typically used at effective doses, in particular at doses likely to be phytotoxic to the plant thus treated, i.e. at doses at which phytotoxicity affects the integrity of the treated plant.

[0028] It is understood that the said terpene(s) as a plant protection product is / are distinct from caryophyllene.

[0029] Typically, terpenes can be chosen from aromatic and / or hydroxyl terpenes. Eugenol, and others, are examples of terpenes. thymol, limonene, geraniol, cinnamaldehyde, eucalyptol, carvone, citral, carvacrol, menthol, menthone and citronellol, more specifically eugenol.

[0030] According to one embodiment, the term "terpene" refers to one or more pure terpenes, and / or one or more essential oils containing them.

[0031] Thus, according to one embodiment, said terpene treatment comprises the application of an essential oil chosen from clove oil, sweet orange oil, lemongrass oil, cinnamon oil, mint oil; peppermint oil, geranium oil, eucalyptus oil, oregano oil, rosemary oil, rose oil, savory oil.

[0032] According to the invention, the phytosanitary treatment is complemented by the application of caryophyllene, which is used here for its role as an adjuvant to the phytosanitary product, in that it prevents the risk of phytotoxicity or reduces the phytotoxicity of said phytosanitary product.

[0033] The plant protection product and caryophyllene can be applied simultaneously, typically within the same treatment composition.

[0034] Thus, according to one embodiment, the process according to the invention comprises the application of a composition comprising caryophyllene and the plant protection product.

[0035] Alternatively, the plant protection product and caryophyllene may be applied separately, typically in two distinct compositions. In this case, the application of the two compositions may be simultaneous or separate.

[0036] By "plants," we mean any plant in the process of being cultivated, such as agricultural and horticultural plants, as well as plant products derived from these plants, such as fruits or vegetables in the field or harvested, i.e., in the process of being stored.

[0037] Horticultural and agricultural plants are understood to mean plants related to market gardening, vegetable gardening, arboriculture and floriculture. These plants and products may include, in particular, vegetable and fruit crops, oilseeds and cereals, fruits or vegetables such as solanaceous plants (tomato, eggplant, potato), and more specifically cucurbits (melon, cucumber), legumes (bean), carrot, salsify, lettuce, endive, artichoke, chard, celery, spinach, salad greens, radish, cucumbers, melons, watermelons, and fruit trees and fruits, etc.

[0038] According to the invention, the caryophyllene / plant protection product ratio is between 2 / 8 and 9 / 1 by weight.

[0039] According to one embodiment, the caryophyllene / plant protection product ratio is between 2 / 1 and 9 / 1 by weight.

[0040] According to one embodiment, the process can therefore be implemented by one or two treatment compositions.

[0041] According to one embodiment, the process includes the application of a treatment composition comprising caryophyllene, the plant protection product, and optionally one or more acceptable emulsifiers and / or vehicles, and water.

[0042] According to one embodiment, the treatment composition consists of these ingredients, in that it is free of additional agents, in particular solvent.

[0043] The term “emulsifier” refers to surfactants or emulsifiers, these terms being used interchangeably here.

[0044] Various emulsifiers are known per se. According to the present invention, "emulsifier" means any type of agent commonly used to improve emulsification in water, such as ethoxylated fatty alcohols, ethoxylated fatty acids, ethoxylated alkylphenols, sorbitan esters and their ethoxylated derivatives, or any other nonionic or anionic product such as ethoxylated sodium lauryl sulfate.

[0045] The invention is not, however, limited to the use of these particular surfactants.

[0046] The term “acceptable vehicle” refers to a formulation compatible with use on plants and / or in food and more particularly refers to liquid or solid substrates used for the application of active material, in particular to improve their effectiveness, diffusion, selectivity and / or safety.

[0047] Acceptable vehicles may include, in particular, lecithin, bentonite, cyclodextrins, hydroxyapatite and [3-tricalcium phosphate (TCP).

[0048] Typically the treatment composition(s) can be obtained from concentrates.

[0049] According to one embodiment, the concentrate is diluted by mixing with water.

[0050] According to one embodiment, the process therefore comprises

[0051] the preparation of a concentrate by mixing caryophyllene, the plant protection product, and possibly one or more acceptable emulsifiers and / or vehicles;

[0052] the preparation of said treatment composition by diluting said concentrate in water.

[0053] The dilution is typically between 0.01 and 10% (by volume), in particular from 0.1 to 5%, typically between 0.2 and 1%, i.e. 2000 to 10000 ppm.

[0054] The term “concentrate” refers to a “pre-mix” type formulation intended to be diluted in a solvent, typically water, prior to the application of the diluted composition thus obtained, referred to herein as the “treatment composition”.

[0055] The concentrate can typically be an organic solution, an aqueous solution, or an emulsion. Advantageously, the concentrate can comprise the plant protection product and caryophyllene, optionally diluted in water or an organic solvent, or mixtures thereof, possibly in the presence of one or more acceptable emulsifying agents and / or vehicles.

[0056] According to one embodiment, the concentrate consists of these ingredients, in that it is free of additional agents, in particular solvent.

[0057] According to one embodiment, said concentrate contains from 0 to 60% of surfactant(s) (by weight).

[0058] Concentrates can be prepared conventionally in themselves by simply mixing their constituents.

[0059] The treatment according to the invention can typically be carried out by immersion, spraying, sprinkling, watering, irrigation or spreading.

[0060] Generally, the diluted composition(s) is / are applied to the field in one or more applications during the period between sowing and fruit or vegetable ripening. It / They can also be applied post-harvest, during storage, to harvested plant products such as fruits, vegetables, or tubers.

[0061] Typically, the treatment according to the invention can be carried out once or several times during the plant's growing stage. The treatment can therefore be repeated several times, depending on the duration of the growing or storage cycle, the risk of pest infestation, and / or the effectiveness of the plant protection treatment. According to an advantageous aspect, only one treatment is carried out.

[0062] Advantageously, the treatment according to the invention can be carried out at ambient temperature, or at the usual application temperature of the phytosanitary treatment.

[0063] The amount of caryophyllene applied depends on the type of fruit or vegetables concerned, the application method selected, and the aggressiveness of the plant protection treatment. It can also be related to the amount of emulsifiable concentrate. Typically, this treatment composition is applied at a dose of between 1 and 50 L / ha, relative to the concentrate, once or several times during the plant's growing stage or the storage of plant products.

[0064] According to another object, the present invention also relates to the use of caryophyllene as a protective adjuvant for a plant protection product, the application of the plant protection product and that of caryophyllene being able to be simultaneous or separate, characterized in that the caryophyllene / plant protection product ratio is between 2 / 8 and 9 / 1 by weight.

[0065] The term “adjuvant” refers, in the context of the invention, to the use of caryophyllene as a functional additive, capable of reducing the phytotoxicity of the plant protection product at the dose considered, and thus ultimately allowing the application dose of said plant protection product to be increased and therefore ultimately improving the effectiveness of said plant protection treatment.

[0066] According to another object, the invention further relates to the use of caryophyllene as a protective solvent in a composition comprising a plant protection product, characterized in that the caryophyllene / plant protection product ratio is between 2 / 8 and 9 / 1 by weight.

[0067] The term “solvent” here refers to the excess amount in concentration, weight or volume of caryophyllene in relation to said plant protection product and its ability to solubilize said terpene.

[0068] Thus, a composition comprising a plant protection product such as a terpene, in solution in caryophyllene such that the caryophyllene / plant protection product ratio is between 2 / 8 and 9 / 1 by weight, is a particular object of the invention.

[0069] More particularly, it aims at a concentrate consisting of an essential oil as defined above, caryophyllene, one or more emulsifiers and water, such that the caryophyllene / terpene ratio is between 2 / 8 and 9 / 1 by weight.

[0070] According to one embodiment, said concentrate comprises: - 0 to 70% by weight of caryophyllene; - 5 to 30% by weight of terpene; - from 0 to 60% by weight of emulsifier(s);

[0071] in water.

[0072] Also, it aims at a plant treatment composition consisting of an essential oil as defined above, caryophyllene, one or more emulsifiers and water, such that the caryophyllene / terpene ratio is between 2 / 8 and 9 / 1 by weight.

[0073] According to one embodiment of the use of the invention, the caryophyllene / terpene ratio is between 2 / 1 and 9 / 1 by weight.

[0074] The following examples are given by way of illustration and not limitation of the present invention. EXAMPLES

[0075] The experiment was carried out on oranges which had been previously inoculated with spores of the fungus Geotrichum Candidum.

[0076] Unless otherwise stated, percentages are given by weight. 1. Preparation of emulsifiable concentrates and treatment compositions. 1. Several emulsifiable concentrates were prepared:

[0077] Different concentrates with varying caryophyllene contents were prepared from a mixture of 6 moles of ethoxylated oleic acid and 10 moles of ethoxylated lauric alcohol.

[0078] Concentrate £ C 1) at 8% clove oil, said oil containing 85% eugenol and 10% beta-caryophyllene _

[0079] For this purpose, a mixture of emulsifiers was prepared consisting of 25.8% of 6 mole ethoxylated oleic acid and 4.7% of 10 mole ethoxylated lauric alcohol.

[0080] These 30.5% emulsifiers were then dispersed in 61.5% water, to which 8% clove oil was then added.

[0081] Concentrate (C2) supplemented with caryophyllene (20%).

[0082] The same mixture of emulsifiers was added to 41.5% water, then 8% clove oil and 20% caryophyllene were added.

[0083] Concentrate (C3) supplemented with caryophyllene (40%):

[0084] A third mixture was prepared with the same mixture of emulsifiers, 21.5% water, 8% clove oil and 40% caryophyllene.

[0085] Concentrate (C 4) without clove oil, supplemented with caryophyllene (40%):

[0086] The emulsifier mixture was supplemented with 29.5% water and 40% caryophyllene

[0087] Cl'-C4' concentrates were prepared in the same way by replacing clove oil with sweet orange oil which contains 95% limonene.

[0088] The caryophyllene / essential oil ratio (by weight) for each of the concentrates is summarized below:

[0089] [Tables 1] Car. / oil Car. / oil Cl na Cl' na C2 20 / 8=2.5 C2' 20 / 8=2.5 C3 40 / 8=5 C3' 40 / 8=5 C4 na C4' na 1. Preparation of treatment compositions

[0090] Each of these 4 emulsifiable concentrates C1-C4 was diluted in water at a level of 1.5% by volume, giving rise to 4 corresponding dispersions D1-D4.

[0091] Each of these 4 emulsifiable concentrates Cl'-C4' was diluted in water at a rate of 1.5% by volume, giving rise to 4 corresponding dispersions Dl'-D4'.

[0092] 2. Immersion treatment

[0093] 5 lots of 20 Navelina variety oranges of the same size and stage of ripeness identical ones were randomized.

[0094] The first batch, simply immersed in water, constituted the control.

[0095] The four other batches of oranges were each immersed in dispersion D1, D2, D3 or D4, respectively.

[0096] 14 days later the fruits were examined for rot count and skin damage (“damage”), assessed as a percentage of affected surface area.

[0097] The results of these counts are reported below:

[0098] [Tables2] Witness DI D2 D3 D4 % rotten 58.8 25.4 19.6 18.9 52.7 % damage 0 7.6 1.7 0.2 0

[0099] The results confirm that:

[0100] Rot is inhibited by clove oil / eugenol.

[0101] The damage to the skin illustrates phytotoxicity, caused by clove oil / eugenol, it being understood that the damage is inhibited in the presence of an excess of caryophyllene. 1. Spray treatment

[0102] Treatment 1: The 4 dispersions D1-D4 and the water control were applied in the greenhouse by spraying on 5 batches of tomato plants, after dilution to 0.7% in water, at a dose of 100 liters per 1000 m2, using the same procedure for the 4 batches of product and the control.

[0103] After 10 days, the lots were treated with the control or one of the dispersions Dl'-D4' corresponding to D1-D4 respectively.

[0104] The plants were examined 10 days later.

[0105] The checks carried out concerned the estimation of damage to leaves and fruit, always determining the percentage of surface area affected in both cases.

[0106] The results of these counts are reported below:

[0107] [Tables3] Control D1+D1' D2+D2' D3+D3' D4+D4' Fruits 0 5.2 0.5 0.2 0 Leaves 0.1 14.3 2.5 0.2 0

[0108] The conclusion is that the first caryophyllene / oil ratio of 2.5 is capable of reducing the damage caused by essential oils by 5 times, while the caryophyllene / oil ratio of 5 brings the level of damage to almost 0.

[0109] Caryophyllene alone shows no aggressiveness towards plants.

[0110] These results demonstrate that excess caryophyllene, particularly in a caryophyllene / essential oil ratio greater than 2, helps to protect plants against the aggressiveness of essential oils.

Claims

Demands

1. A method for protecting plants against the phytotoxicity of a treatment with a plant protection product, said method comprising the addition of caryophyllene to the plant protection treatment, the application of the plant protection product and that of caryophyllene being able to be simultaneous or separate, characterized in that the caryophyllene / plant protection product ratio is between 2 / 8 and 9 / 1 by weight.

2. A protection method according to claim 1 wherein the caryophyllene / plant protection product ratio is between 2 / 1 and 9 / 1 by weight.

3. A protection method according to claim 1 or 2 wherein said plant protection product is selected from insecticides, fungicides, bactericides, nematicides, biostimulants, fertilizers, food additives, used in the field and / or post-harvest, of natural or synthetic origin.

4. A process according to any one of the preceding claims wherein said plant protection product is selected from terpenes such as eugenol, thymol, limonene, geraniol, cinnamaldehyde, eucalyptol, carvone, citral, carvacrol, menthol, menthone, citronellol and mixtures thereof.

5. A process according to any one of the preceding claims wherein said plant protection product is selected from essential oils, such as clove oil, sweet orange oil, lemongrass oil, cinnamon oil, mint oil, peppermint oil, geranium oil, eucalyptus oil, oregano oil, rosemary oil, rose oil, savory oil and mixtures thereof.

6. A protection method according to any one of the preceding claims, wherein the method comprises the application of a treatment composition comprising caryophyllene, the plant protection product, and optionally one or more acceptable emulsifiers and / or vehicles, and water.

7. A process according to claim 6 further comprising: The preparation of a concentrate by mixing caryophyllene, the plant protection product, and optionally one or more acceptable emulsifiers and / or vehicles; the preparation of said treatment composition by diluting said concentrate in water.

8. A method according to any one of the preceding claims, wherein the application is carried out by immersion, spraying, sprinkling, watering, irrigation or spreading.

9. Treatment method according to any one of claims 6, 7 and 8 wherein said treatment composition is applied at a dose of 1 to 50 L / ha relative to the concentrate, once or several times during the plant growing stage or the storage period of the plant products.

10. Processing method according to claim 7 wherein the concentrate is diluted to a level of 0.01 to 10% (by volume) in water.

11. Processing method according to any one of the preceding claims wherein the plants are selected from agricultural and horticultural plants, plant products derived from these plants, such as fruits or vegetables in the field, or in storage.

12. Use of caryophyllene as a protective adjuvant for a plant protection product, the application of the plant protection product and that of caryophyllene being able to be simultaneous or separate, characterized in that the caryophyllene / plant protection product ratio is between 2 / 8 and 9 / 1 by weight.

13. Use of caryophyllene as a protective solvent in a composition comprising a plant protection product, characterized in that the caryophyllene / plant protection product ratio is between 2 / 8 and 9 / 1 by weight.

14. Use according to any one of claims 12 or 13, such that the caryophyllene / plant protection product ratio is between 2 / 1 and 9 / 1 by weight.

Citation Information

Patent Citations

  • PLANT PROTECTION METHOD USING CARYOPHYLLENE

    FR3127367A1

  • Reducing phytotoxic effects, especially skin damage, caused by physical and chemical treatment of fruit and vegetables, by application of lecithins and their derivatives

    FR2853495A1

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    FR2857564A1

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