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    • 专利摘要:
    The present invention relates to a composition for improving the stress tolerance of plants comprising at least one oligomer of a hydroxycinnamic acid derivative, and optionally a solubilizing agent in water. The present invention also relates to methods for improving the stress tolerance of a plant comprising applying such a composition to the plant.
    公开号:BE1023236B1
    申请号:E2016/0011
    申请日:2016-01-21
    公开日:2017-01-06
    发明作者:Carlos CABRERA PINO Juan；Guillaume Wegria
    申请人:Fyteko Sprl；
    IPC主号:
    专利说明:

    BIOACTIVE COMPOSITION FOR IMPROVING STRESS TOLERANCE
    PLANT
    FIELD OF THE INVENTION
    The present invention relates to a bioactive composition for improving the tolerance of plants to stress. In particular, the present invention relates to a composition comprising at least one oligomer of hydroxycinnamic derivatives which makes it possible to improve plant tolerance to abiotic and biotic stress, to increase the survival of a plant under unfavorable environmental conditions, to obtain a better growth and provide a substantial yield advantage.
    STATE OF THE ART
    Crop management is most often carried out by chemicals, for example fertilizers or pesticides, which provide effective protection of plants but often interfere with other biological components of the environment, creating irreversible imbalances. In addition, these chemicals can cause serious damage to consumer health because of their residues in food products. From this observation, it appears the need to gradually reduce the use of chemicals in agriculture. Today, agriculture is increasingly focused on product quality as well as environmental, hygienic and sanitary aspects. As a result, agricultural practices tend to evolve towards more sustainable management of agricultural crops, in order to ensure the quantitative and qualitative properties of the product.
    Over the past decade, studies on alternative technologies that are more environmentally friendly have continued to grow and have offered a wide range of options, including agronomic, physical and biological controls (Verma et al. , Biochem Eng Journal, 2007, 37: 1-20, Shoresh et al., Annu Rev Phytopathol, 2000, 48: 21-43, Bharti et al., J Sei Food Agric 2013, 93: 2154-2161, Yeoh. et al., Mol Biol Rep. 2013, 40: 147-158). In this context, the use of biopesticides and biostimulants is certainly one of the most promising options.
    Biopesticides are a type of pesticide derived from natural materials such as animals, plants, bacteria and some minerals. They fall into three broad classes: (1) Microbial pesticides consist of a micro-organism as an active ingredient. For example, fungi that control certain weeds; (2) Plant Protectors (PIPs) are pesticide substances that plants produce from genetic material that has been added to plants and (3) Biochemical biopesticides are natural bioactive compounds or synthetic derivatives of bioactive compounds that are structurally similar (and functionally identical) to their natural counterparts. Elicitors that are able to trigger immune defense responses in plants are one of the most used biopesticides. In general, biochemical biopesticides are characterized by a non-toxic mode of action that may affect the growth and development of a pest, its ability to reproduce, or the ecology of the pest.
    Plant biostimulants are bioactive substances and / or microorganisms whose function when applied to plants or the rhizosphere, is to stimulate their natural processes in order to improve / increase the absorption of nutrients , nutrient efficiency, abiotic stress tolerance and crop quality. Biostimulants are able to improve the quality and yield of crops at a lower cost, by manipulating the plant's metabolism, while reducing the adverse environmental impacts associated with the use of chemical compounds.
    Biostimulants do not provide nutrients directly to plants and they have no direct action against pathogens, but they increase the ability of plants to withstand different abiotic and biotic constraints: lack of water, high heat, excessive moisture, high salinity, toxic minerals or compounds, diseases or parasites (bacteria, viruses, fungi, parasites or harmful insects). These stress conditions have a negative impact on agricultural production. Also, the use of biostimulant, even at low concentration of the ingredient / principle / compound helps to limit the use of fertilizers and pesticides by improving the growth and overall health of the crop plants. The agricultural world therefore has an important interest in improving crop performance with the aim of reducing the total amount of chemical compounds used.
    Biostimulants for plants usually belong to one of three main categories: plant hormones, amino substances and humic substances. In accordance with the foregoing, plant biotimulants may for example include compositions based on algae extracts, humic acids, amino acids, salicylic acid, bio-solids, hydrolysed proteins, silicate and the like. or synthetic compounds. Cinnamic acid and its 4-hydroxy-substituted derivatives (ie p-coumaric acid, caffeic acid, ferulic acid and sinapic acid) form a family of natural products abundantly present in plants and generally known as cinnamates. In particular, ferulic acid, various diflerulic acids and even triferulic acids are important components of the cell walls of certain plants. In cell walls, these compounds are esterified to arabinose groups derived from glucuronoarabinoxylans, a predominant component of the hemicellulose matrix of cell walls. For example, ferulic acid is considered to be the predominant phenolic crosslinking agent of the cell walls of the herb, which plays an important role in the extensibility of the latter (Carpita NC Annu, Rev. Plant Physiol, Plant Mol Biol. 1996, 47: 445-476).
    JP-H-10338603 discloses cinnamic acid as a useful compound for preventing leaf and root death caused by pathogenic bacteria. In addition, Li et al. (Biologia Plantarum 2013, 57 (4): 711-717) showed that cucumber seedlings watered for 2 days with a nutrient solution 'Hoagland' containing ferulic acid could help protect plants from the stress of dehydration.
    However, cinnamic acids and ferulic acid have been presented for several years as phytotoxic agents (Turner et al., Journal of Chemical Ecology, 1975, 1 (1): 41-58, Rasmussen et al, Journal of Chemical Ecology. 1977, 3 (2): 197-205, Liebl et al., Journal of Chemical Ecology, 1983, 9 (8): 1027-1043, Blum et al., Journal of Chemical Ecology, 1984, 10 (8): 1169 1191) and are used by many plants as allelochemical inhibitors (Einhellig et al, Journal of Chemical Ecology 1984, 10 (1): 161-170, Dos Santos et al, Journal of Chemical Ecology, 2004). , (6): 1203-1212, Yu et al., Journal of Chemical Ecology, 1994, 20 (1): 21-31, Lehman et al., Journal of Chemical Ecology, 1999, 25 (11): 2585- 2600).
    The Applicant has surprisingly found that oligomers of hydroxycinnamic derivatives promote the growth and development of plants under various stress conditions, particularly in adverse environmental conditions such as drought or mineral stress. This growth stimulation promotes the efficient use of water by the plant in a wide range of drought stress, ranging from light and seasonal water stress to severe and prolonged drought. This range of water stress situations is usually accompanied by heat stress.
    The present invention thus relates to a composition comprising at least one oligomer of hydroxycinnamic derivatives for improving the tolerance of a plant to stress. ABSTRACT
    The present invention relates to a composition for improving the stress tolerance of a plant comprising at least one oligomer of hydroxycinnamic acid derivative. In one embodiment, said at least one hydroxycinnamic acid derivative oligomer of the invention has a degree of polymerization of at least 2.
    In one embodiment, said at least one hydroxycinnamic acid derivative is selected from the group consisting of ferulic acid, p-coumaric acid, caffeic acid and sinapic acid. In one embodiment, the composition of the invention comprises at least one ferulic acid oligomer, preferably diferulic acid.
    In one embodiment, the composition of the invention comprises from 0.0001 to 200 ppm (parts per million) of said at least one oligomer of hydroxycinnamic acid derivative, preferably from 0.001 to 100 ppm, more preferably from 0.005 to 50 ppm. .
    In one embodiment, the composition of the invention comprises at least 10% of hydroxycinnamic acid derivative dimer, expressed as a percentage relative to the total of hydroxycinnamic derivative oligomers of the composition, preferably at least 20%, more preferably at least 30%.
    According to one embodiment of the invention, the composition is intended to improve the stress tolerance of a plant, wherein said stress is biotic or abiotic. In one embodiment, said abiotic stress is selected from the group consisting of water stress, osmotic stress, heat stress, nutrient deficiencies, and chemical stresses generated by pollutant metallic or organic elements on the soil where said growth occurs. plant, more preferably water stress, drought or osmotic stress.
    The present invention also relates to a composition for improving the stress tolerance of a plant as described above, further comprising at least one solubilizing agent in water.
    In one embodiment, said at least one water solubilizing agent of the invention is selected from the group consisting of polysaccharides and polyols. In a particular embodiment, said at least one solubilizing agent in water is a polysaccharide selected from the group comprising chitosan, chitin, chitin-glucan, carboxymethylcellulose, pectin, hemicellulose, preferentially chitosan .
    Another subject of the invention is a sprayer comprising a composition as described above.
    The present invention further relates to a plant seed, wherein said seed is coated with a composition as described above.
    Another object of the invention is the use of a composition comprising at least one oligomer of hydroxycinnamic acid derivative to improve the stress tolerance of a plant.
    The present invention further relates to a method for improving the stress tolerance of a plant comprising applying a composition as described above.
    DEFINITIONS
    Unless otherwise indicated, all terms used in the disclosure of the invention, including technical and scientific terms, have the same meaning as commonly understood by those skilled in the art to which this invention belongs. For further explanation and to better appreciate the teaching of the present invention, the definitions of certain terms are provided below. When specific terms are defined in the context of a particular aspect or embodiment, the definition is intended to be applied throughout this document, ie also in the context of other aspects or embodiments. , unless otherwise stated. In the present invention, the following terms have the following precise meanings: "Oligomer" refers to a macromolecule consisting of several monomeric units repetitively connected to one another. In one embodiment, the oligomers of the invention are composed of two, three, four or more monomers. "Polymerization degree" refers to the number of monomeric units in the oligomer of the invention. In one embodiment, the degree of polymerization of said at least one hydroxycinnamic acid derivative oligomer is at least 2. "Oligoferulae" refers to an oligomer of ferulic acid, also called ferulate oligomer. In particular, the dimer of ferulic acid is an oligomer consisting of two monomeric ferulic acids linked by covalent bonds. Ferulic acid dimers may also be referred to as diferulic acid or diferulate. "Enhance", in the context of the present invention, can be replaced by inducing, augmenting, reinforcing and analogous terms. - "Tolerance" means the ability of a plant to withstand stress without significant changes in its metabolism, growth, productivity and / or viability. In one embodiment of the invention, the stress may be abiotic stress or biotic stress. - "Abiotic stress" refers to stress that occurs due to non-living factors influencing the environment in which the plant lives. - "Biotic stress" means stress that occurs as a result of damage caused to plants by other living organisms, such as bacteria, viruses, fungi, parasites, pests and beneficial insects, weeds and other cultivated or native plants . - "ppm" refers to parts per million, or one part per 1,000,000 parts. - "Approximately" preceding a value means plus or minus 10% of said value.
    DETAILED DESCRIPTION
    The present invention relates to a composition for improving plant tolerance under adverse environmental conditions comprising at least one hydroxycinnamic acid derivative oligomer. In one embodiment, the adverse environmental conditions are also called stress.
    In one embodiment, said at least one hydroxycinnamic acid derivative oligomer of the composition of the invention is a monohydroxycinnamic acid oligomer. Examples of monohydroxycinnamic acids include, but are not limited to, coumaric acids such as, for example, p-coumaric acid (4-hydroxycinnamic acid), o-coumaric acid (2-hydroxycinnamic acid) and m-coumaric acid (3-hydroxycinnamic acid), or a mixture thereof.
    In another embodiment, said at least one hydroxycinnamic acid derivative oligomer of the composition of the invention is an oligomer of a dihydroxycinnamic acid. Examples of dihydroxycinnamic acids include, but are not limited to, caffeic acid (3,4-dihydroxycinnamic acid), umbellic acid (2,4-dihydroxycinnamic acid), 2,3-dihydroxycinnamic acid, 2,5-dihydroxycinnamic acid and 3,5-dihydroxycinnamic acid, or a mixture thereof.
    In another embodiment, said at least one hydroxycinnamic acid derivative oligomer of the composition of the invention is an oligomer of a trihydroxycinnamic acid. Examples of trihydroxycinnamic acids include, but are not limited to, 3,4,5-trihydroxycinnamic acid and 3,4,6-trihydroxycinnamic acid, or a mixture thereof.
    In another embodiment, said at least one hydroxycinnamic acid derivative oligomer of the composition of the invention is a methylated acid oligomer. Examples of methylated hydroxycinnamic acids include, but are not limited to, ferulic acid (3-methoxy-4-hydroxycinnamic acid), 5-hydroxyferulic acid and sinapinic acid (3,5-dimethoxy-4) - hydroxycinnamic acid), or a mixture thereof.
    In one embodiment, the composition of the invention comprises at least one ester or oligomeric conjugate of hydroxycinnamic acid derivative. Examples of esters or conjugates of hydroxycinnamic acid derivatives include, but are not limited to, caftaric acid, choric acid, chlorogenic acid and costaric acid, or a mixture thereof .
    In one embodiment, said at least one hydroxycinnamic acid derivative of the invention is selected from the group consisting of ferulic acid, coumaric acid, caffeic acid and sinapinic acid, or a mixture of those -this. In a preferred embodiment, said at least one hydroxycinnamic acid derivative of the invention is ferulic acid or coumaric acid, or a mixture thereof. In another more preferred embodiment, said at least one hydroxycinnamic acid derivative of the invention is ferulic acid or p-coumaric acid, or a mixture thereof.
    In one embodiment, said at least one hydroxycinnamic acid derivative oligomer of the composition of the invention is selected from the group consisting of ferulic acid oligomers, coumaric acid oligomers, caffeic acid oligomers and oligomers of sinapinic acid, or a mixture thereof. In a preferred embodiment, said at least one hydroxycinnamic acid derivative oligomer of the composition of the invention is an oligomer of ferulic acid or coumaric acid oligomer, or a mixture thereof. In a more preferred embodiment, said at least one hydroxycinnamic acid derivative oligomer of the composition of the invention is an oligomer of ferulic acid or a p-coumaric acid oligomer, or a mixture thereof. this.
    In one embodiment, said at least one hydroxycinnamic acid derivative oligomer of the composition of the invention has a degree of polymerization of at least two.
    In one embodiment, said at least one hydroxycinnamic acid derivative oligomer of the composition of the invention has a degree of polymerization of 2, 3, 4, 5, 6, 7, 8, 9, 10 or more. Accordingly, in one embodiment, said at least one hydroxycinnamic acid derivative oligomer is a dimer, trimer, tetramer, pentamer, hexamer, heptameter, octamer, nonamer, decamer, or more. . In a particular embodiment, said at least one oligomer of hydroxycinnamic acid derivative of the composition of the invention is a dimer.
    According to one embodiment of the invention, the composition comprises a dimer of ferulic acid (also known as diferulic acid or diférulate). In one embodiment, the composition does not include ferulic acid.
    In one embodiment, the composition of the invention comprises a mixture of oligomers of hydroxycinnamic acid derivatives having different degrees of polymerization. By way of example, but not limited to, the composition may comprise a mixture of ferulic acid dimers, trimers, tetramers, hexamers and more.
    The effective concentration of the hydroxycinnamic acid derivative oligomer in the composition of the invention will vary depending on the type of hydroxycinnamic acid derivative oligomer, the cultures to be treated, the magnitude of the stress (e.g. drought), the desired result, and the crop phase of the plant, among other factors.
    In one embodiment, the composition of the invention comprises from 0.0001 to 200 ppm (parts per million) of said at least one hydroxycinnamic acid derivative oligomer, preferably from 0.001 to 100 ppm, more preferably from 0.005 to 50 ppm. .
    In another embodiment, the composition of the invention comprises from 1 to 200 ppm of said at least one hydroxycinnamic acid derivative oligomer, preferably from 5 to 100 ppm, more preferably from 10 to 50 ppm. In a particular embodiment, the composition of the invention comprises about 15 or 16 ppm of said at least one hydroxycinnamic acid derivative oligomer. In a particular embodiment, the composition of the invention comprises about 50 ppm of said at least one hydroxycinnamic acid derivative oligomer.
    In another embodiment, the composition of the invention comprises between 0.0001 and 10 ppm of said at least one oligomer of hydroxycinnamic acid derivative, preferably from 0.001 to 5 ppm, more preferably from 0.005 to 2.5 ppm.
    In one embodiment, the composition of the invention comprises from 0.0001 to 200 mg / L of said at least one oligomer of hydroxycinnamic acid derivative, preferably from 0.001 to 100 mg / l, more preferably from 0.005 to 50 mg / ml. L. In another embodiment, the composition of the invention comprises from 1 to 200 mg / L of said at least one oligomer of hydroxycinnamic acid derivative, preferably from 5 to 100 mg / l, more preferably from 10 to 50 mg / L. In a particular embodiment, the composition of the invention comprises about 15 or 16 mg / L of said at least one hydroxycinnamic acid derivative oligomer. In a particular embodiment, the composition of the invention comprises about 50 mg / L of said at least one oligomer of hydroxycinnamic acid derivative. In another embodiment, the composition of the invention comprises between 0.0001 and 10 mg / L of said at least one oligomer of hydroxycinnamic acid derivative, preferably from 0.001 to 5 mg / L, more preferably from 0.005 to 2.5 mg / L.
    In one embodiment, the composition of the invention comprises from 1.10'8 to 2.10-2% of said at least one oligomer of hydroxycinnamic acid derivative, preferably from 1.10'7 to 1.10'2%, more preferably from 5 to 10% by weight. '7 to 5.10'3%. In another embodiment, the composition of the invention comprises from 1.10'4 to 2.10'2% of said at least one oligomer of hydroxycinnamic acid derivative, expressed as a percentage by weight relative to the total weight of the composition, of Preferably from 5.10-4 to 1.1 Or2%, more preferably from 1.10-3 to 5.10-3%, In a particular embodiment, the composition according to the invention comprises about 1.5 × 10 -3 or 1.6 × 10 -3% of said at least one oligomer of hydroxycinnamic acid derivative, expressed as a percentage by weight relative to the total weight of the composition In a particular embodiment, the composition of the invention comprises approximately 5.10'3% of said at least one oligomer of hydroxycinnamic acid derivative, expressed as a percentage by weight relative to the total weight of the composition In another embodiment, the composition of the invention comprises from 1.10'8 to 1.10'3% of said at least one oligomer of hydroxycinn acid derivative amic, expressed as a percentage by weight relative to the total weight of the composition, preferably from 1.10'7 to 5.10'4%, more preferably from 5.10'7 to 2.5.10'4%.
    In another embodiment, the composition of the invention comprises at least 10% of a hydroxycinnamic acid derivative dimer, expressed as a percentage based on the total oligomers of hydroxycinnamic derivatives of the composition, preferably at least 20%. %, more preferably at least 30%.
    The composition according to the invention may further comprise a co-formulant selected from the group comprising: diluting agents, buffering agents, surfactants (dispersing agents, anti-foaming or defoaming agents, spreader, penetration promoters) adjuvant or humectants), antifreeze agents (urea, ethylene glycol, propylene glycol or glycerol), preservatives (potassium sorbate, paraben and its derivatives, 1,2-benzisothiazol-3 ( 2H) -one or essential oils), absorbents (including corn starch or sawdust), thickeners (including clays or xanthate gum), tackifiers (including latex, silicone or alkylated alkyls), crop protection adjuvants, or a mixture thereof.
    According to one embodiment, the composition of the invention further comprises a diluting agent. As used herein, the term "diluting agent" refers to an aqueous or non-aqueous solution that is used to dilute said at least one hydroxycinnamic acid derivative oligomer of the composition. Examples of diluents include, but are not limited to, water, saline, polyethylene glycol, propylene glycol, ethanol, oil and the like.
    According to another embodiment, the composition of the invention further comprises a buffering agent. As used herein, the term "buffering agent" refers to an aqueous solution comprising a mixture of acids and bases which is used to stabilize the pH of the composition. Examples of buffering agents include, but are not limited to, TRIS, phosphate, carbonate, acetate, citrate, glycolate, lactate, borate, tartrate, cacodylate, ethanolamine, glycine, imidazole and the like.
    In one embodiment, the composition of the invention has an acidic pH. As used herein, the term "acidic pH" refers to a pH value of less than or equal to 7. In one embodiment, the composition has a pH of less than or equal to 6. In a particular embodiment, the composition of the invention has a pH of about 5.5.
    According to one embodiment, the composition of the invention further comprises an organic acid. As used herein, the term "organic acid" refers to an organic compound with acidic properties. Preferably, the organic acid is a carboxylic acid. Examples of organic acids include, but are not limited to, lactic acid, succinic acid, malic acid, and citric acid. In a particular embodiment, the composition of the invention comprises lactic acid. The invention also relates to a composition for improving the tolerance of plants to stress as described above, further comprising at least one solubilizing agent, preferably a solubilizing agent in water.
    As used herein, the term "water solubilizing agent" refers to a compound that renders said at least one hydroxycinnamic acid derivative oligomer of the invention soluble or more soluble in water.
    In one embodiment, the solubilizing agent in water is selected from the group consisting of positively or negatively charged biopolymers, polysaccharides, and polyols. In a preferred embodiment, the solubilizing agent in water is a polysaccharide or sulfated polysaccharide. In one embodiment, the polysaccharide or sulfated polysaccharide is a cationic polysaccharide.
    In one embodiment, the solubilizing agent in water is a polysaccharide selected from the group consisting of chitosan, chitin, chitin-glucan, carboxymethylcellulose, pectin, hemicellulose. In a particular embodiment, the solubilizing agent in water is chitosan or chitin-glucan.
    In one embodiment, the solubilizing agent in water is a polyol selected from the group consisting of mannitol and sorbitol.
    According to one embodiment of the invention, the composition comprises diferulic acid (diférulate) and a polysaccharide, preferably a cationic polysaccharide. According to a preferred embodiment of the invention, the composition comprises diférulic acid (diférulate) and chitosan.
    In one embodiment, the composition of the invention comprises from 0.01% to 10% of the said at least one solubilizing agent, expressed as a percentage by weight relative to the total weight of the composition, preferably from 0.05% to 5%, more preferably from 0.1 to 2%. In a particular embodiment, the composition of the invention comprises about 0.4% of said at least one solubilizing agent. In another particular embodiment, the composition of the invention comprises about 0.5% of said at least one solubilizing agent.
    In another embodiment, the composition of the invention comprises from 100 to 10,000 ppm of said at least one solubilizing agent, preferably from 500 to 50,000 ppm, more preferably from 1,000 to 20,000 ppm. In a particular embodiment, the composition of the invention comprises about 4,000 ppm of said at least one solubilizing agent. In another particular embodiment, the composition of the invention comprises about 5,000 ppm of said at least one solubilizing agent.
    In another embodiment, the composition of the invention comprises from 1.10 6 to 2.10 3% of said at least one solubilizing agent, preferably from 5.10 6 to 1.10 3%, more preferably from 1.10 5 to 5.10 "4%. In a particular embodiment, the composition of the invention comprises from 5.10 5 to 2.5 × 10 -4% of said at least one solubilizing agent.
    In another embodiment, the composition of the invention comprises from 0.01 to 20 ppm of said at least one solubilizing agent, preferably from 0.05 to 10 ppm, more preferably from 0.1 to 5 ppm. In a particular embodiment, the composition of the invention comprises from 0.5 to 2.5 ppm of said at least one solubilizing agent.
    According to one embodiment, the hydroxycinnamic acid derivative oligomers of the invention are prepared "in situ" by polymerization of oligomers of the enzyme catalyzed hydroxycinnamic acid derivatives in the presence of a solubilizing agent as described herein. -above. In this case, the solubilizing agent also acts as a matrix controlling the reaction of the polymerization. In a particular embodiment, the solubilizing agent acting as a polymerization matrix is chitosan and the enzyme is a laccase.
    According to one embodiment, the composition of the invention may further comprise any biostimulant, plant growth regulators or hormone-containing products known in the art to enhance the stress tolerance of a plant such as, for example, for example, humic acids, fulvic acids, fiicoidan, antiperspirants, oligosaccharides and the like.
    In one embodiment, the stress for which the composition of the invention improves plant tolerance is abiotic stress or biotic stress.
    As used herein, the term "tolerance" can be replaced by resistance or defense, protection, support, strength, toughness, endurance, stamina, resilience, struggle, and the like.
    In one embodiment, the abiotic stress may be water stress, dryness, osmotic stress, heat stress, nutrient deficiency, and chemical stress generated by a metallic or organic pollutant in the soil where the plant grows. In a preferred embodiment, abiotic stress is selected from the group consisting of water stress, drought and osmotic stress.
    Drought tolerance (drought resistance) is a general concept, depending on the different types of reactions that include drought resistance (avoidance of dehydration), tolerance and drought recovery (recovery of a grade). in normal water following a drought). Here, the concept is also extended to erratic rain and the shortage of water (eg related to the change in global warming of the environment.).
    In one embodiment, the composition comprising at least one oligomer of hydroxycinnamic acid derivative is intended to improve the tolerance of a plant to water stress. In another embodiment, the composition comprising at least one oligomer of hydroxycinnamic acid derivative is intended to improve the tolerance of a plant to drought. In another embodiment, the composition comprising at least one hydroxycinnamic acid derivative oligomer is intended to improve the tolerance of a plant to osmotic stress.
    In one embodiment, the composition for improving the tolerance of a plant to water stress comprises diférulate. In another embodiment, the composition for improving plant tolerance to drought comprises diferulate. In another embodiment, the composition for improving the tolerance of a plant to osmotic stress comprises diferulate.
    In another embodiment, the biotic stress may be due to bacteria, viruses, fungi, parasites, beneficial insects, pests, weeds, cultivated plants or native plants.
    In one embodiment, the plant of the invention is a monocotyledonous plant. In another embodiment, the plant of the invention is a dicotyledonous plant.
    In one embodiment, the plant of the invention is selected from the group consisting of cotton, flax, vine, fruit, vegetables, horticultural and forestry crops, such as: Rosaceae sp., Ribesioidae sp., Juglandaceae sp. , Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp., Rubiaceae sp., Theaceae sp., Sterculiceae sp., Rutaceae sp., Solanaceae sp. ., Vitaceae sp. Liliaceae sp., Asteraceae sp., Umbelliferae sp., Cruciferae sp., Chenopodiaceae sp., Cucurbitaceae sp., Papilionaceae sp., Such as Graminae sp., Fabacae sp., As well as the genetically modified homologous plants of these cultures.
    In one embodiment, the plant is a food crop selected from the group consisting of wheat, rice, corn, soybean, potato, barley, oats, kidney beans, and millet. In another embodiment, the plant is a plant crop selected from the group consisting of tomato, radish, watercress, cucumber, watermelon, melon, cabbage, Chinese cabbage, shallot, onion , carrot, zucchini, and Arabidopsis thaliana. In another embodiment, the plant is a fruit crop selected from the group consisting of apple, pear, date, peach, kiwi, grape, orange, persimmon, plum, apricot, banana, and mandarin. In another embodiment, the plant is a special crop selected from the group consisting of mustard, ginseng, tobacco, cotton, sesame, sugarcane, sugar beet, peanut and rapeseed. In another embodiment, the plant is a flower crop selected from the group consisting of rose, gerbera, gladiolus, carnation, chrysanthemum, lily, and tulip. In another embodiment, the plant is a forage crop selected from the group consisting of ryegrass, red clover, orchardgrass, alfalfa, and tall fescue.
    In one embodiment, the plant is selected from the group consisting of tomato, radish, wheat, watercress, mustard, soybean and Arabidopsis thaliana. In a particular embodiment, the plant is tomato. In another embodiment, the plant is radish. In another embodiment, the plant is wheat. In another embodiment, the plant is watercress. In another embodiment, the plant is mustard. In another embodiment, the plant is soybean. In another embodiment, the plant is Arabidopsis thaliana.
    Another object of the invention is the use of a composition comprising at least one oligomer of hydroxycinnamic acid derivative as described above to improve the tolerance of a plant to stress. In one embodiment, the composition of the invention is used as a biostimulant to improve the stress tolerance of a plant. In one embodiment, the composition of the invention is a biostimulant composition for improving the stress tolerance of a plant. In one embodiment, the composition of the invention is used as a biopesticide to improve the stress tolerance of a plant. In another embodiment, the composition of the invention is a biopesticide composition for improving the stress tolerance of a plant.
    The composition of the invention may be prepared as a formulation such as, for example, an emulsion, an oil, a hydrate, a powder, a granule, a tablet, an aerosol, a suspension and the like. In one embodiment, if necessary, an emulsifying agent, a suspending agent, a spreading agent, a penetrating agent, a wetting agent, a thickening agent and / or a stabilizing agent may be incorporated in the formulation. In one embodiment, the formulation of the invention may be prepared according to a method known in the art.
    According to one embodiment, the composition or formulation of the invention may be applied to plants by a variety of means, including, but not limited to, sprays, sprinklers, drops, immersion, watering, by coating, by irrigation and in oils.
    According to one embodiment, the composition or the formulation of the invention is applied in liquid form. Examples of liquid forms include, but are not limited to, foliar sprays, lawn sprays, seedbed sprays, seedling immersions, seedling coatings, root coatings, root sprays, watering stems, watering tubers, watering fruit, watering the soil, dripping into the soil and injections into the soil.
    According to another embodiment, the composition or the formulation of the invention is applied in dry form. Examples of dry forms include, but are not limited to, granules, microgranules, powders, pellets, sticks, flakes, crystals, and nuggets.
    In one embodiment, the composition of the invention is adapted to be applied to the plant. In a particular embodiment, the composition of the invention is adapted to be sprayed on the plant. In another embodiment, the composition of the invention is adapted to coat parts of the plant. In a particular embodiment, the composition of the invention is a coating composition, preferably a seed coating composition.
    In one embodiment, the composition of the invention is to be applied to the plant. In one embodiment, the composition may be applied to the aerial parts of the plant, such as leaves and stems. In another embodiment, the composition may be applied to the underground parts of the plant, such as on the roots. In another embodiment, the composition may be applied to the seeds.
    In one embodiment, the composition of the invention must be coated on the plant before planting. In one embodiment, the composition is applied to the plant seeds prior to planting.
    In one embodiment, the composition of the invention may be applied pure or diluted.
    In one embodiment, the concentration of the composition of the invention depends on its application. In one embodiment, the composition of the invention is less concentrated when the composition is adapted to be sprayed on the plant than when the composition is a coating composition, preferably a seed coating composition. As used herein, the term "less concentrated" means that when the composition is adapted to be sprayed on the plant, the composition is at least 2-fold less concentrated than when the composition is a coating composition, in particular a composition seed coating, preferably at least 3.4, 5, 6, 7, 8, 9 or 10 times less concentrated.
    In one embodiment, the composition of the invention comprises from 0.0001 to 10 ppm of said at least one hydroxycinnamic acid derivative oligomer, preferably from 0.001 to 5 ppm, more preferably from 0.005 to 2.5 ppm, when the composition is adapted to be sprayed on the plant. In another embodiment, the composition of the invention comprises from 1 to 200 ppm of said at least one hydroxycinnamic acid derivative oligomer, preferably from 5 to 100 ppm, more preferably from 10 to 50 ppm, when the composition is a coating composition, preferably a seed coating composition.
    In one embodiment, the composition of the invention comprises from 0.01 to 20 ppm of said at least one solubilizing agent, preferably from 0.05 to 10 ppm, preferably from 0.1 to 5 ppm, more preferably from 0.5 to 2.5 ppm, when the composition is adapted to be sprayed on the plant. In another embodiment, the composition of the invention comprises from 0.01 to 10% of said at least one solubilizing agent, expressed as a percentage by weight relative to the total weight of the composition, preferably from 0.05 to 5%, more preferably from 0.1 to 2%, when the composition is a coating composition, preferably a seed coating composition.
    Another object of the invention is a sprayer comprising a composition of the invention as described above. In one embodiment, the sprayer of the invention may be an aerosol spray. As used herein, an aerosol can is a sprayer used with a container that can hold a pressurized liquid such as, for example, a can, bottle or reservoir.
    In one embodiment, the sprayer of the invention can be used manually. Examples of hand-operated sprayers include, but are not limited to, hand pump or hose (ie, cartridge) spray bottles. In another embodiment, the sprayer of the invention can be used mechanically. Examples of mechanically used sprayers may include, but are not limited to, in-line self-propelled sprayers.
    In one embodiment, the spraying of the invention is a foliar spray.
    Another subject of the invention is a plant seed coated with a composition of the invention as described above. The present invention encompasses the plant seeds described above having increased stress tolerance.
    The present invention also relates to a method for improving the stress tolerance of a plant comprising applying to the plant a composition as described above.
    The present invention also relates to a method for improving the stress tolerance of a plant comprising applying to the plant a composition of at least one oligomer of hydroxycinnamic acid derivative, preferably diferulic acid.
    In one embodiment, the method of the invention comprises the application of a composition comprising at least one oligomer of hydroxycinnamic acid derivative and at least one solubilizing agent, preferably chitosan, on the plant.
    In one embodiment, the method of the invention comprises applying the composition of the invention to the plant. In one embodiment, the composition is applied to the aerial parts of the plant, preferably the leaves and / or stems. In another embodiment, the composition is applied to the subterranean parts of the plant, preferably the roots. In another embodiment, the method of the invention comprises coating the seeds of the plant prior to planting.
    According to one embodiment, the plant may be further treated for stress tolerance by any method known in the art.
    Another object of the invention is a method for promoting the growth of plants comprising the application of a composition of the invention to said plant.
    The present invention further relates to a method inducing the activity of phenlylalanine-ammonia lyase (PAL) and / or the production of peroxide (H2Q2) comprising applying a composition of the invention to said plant. PAL is an essential enzyme with a regulatory activity of the phenylpropanoid pathway acting on the precursors of secondary metabolites in the plant, thus playing a key role in a range of plant-pathogen interactions (Morrison and Buxton, Crop Sci. 33: 1264-1268). H2O2 peroxides are produced during one or more outbreaks of resistance activity to a wide variety of host / pathogen interactions and are involved in the stimulation of the hypersensitive response, a mechanism used to prevent the spread of infection with microbial pathogens (Apel and Hirt, Annu Rev Plant Biol 2004, 55: 373-399).
    Another object of the invention is a method for modulating the proline content (Pro) in the plant comprising the application of a composition according to the invention to said plant. The accumulation of pro line is a common physiological response in many plants in response to a wide range of stress. Proline accumulation seems to play an adaptive role in the stress tolerance of the plant, transgenic approaches have confirmed the beneficial effect of proline overproduction in times of stress. In addition, the balance between biosynthesis and Pro degradation is also considered essential in the determination of the osmoprotective and developmental functions of proline (Verbruggen and Hermans, Amino Acids, 2008, 35: 753-759).
    The present invention also relates to a method for increasing the water content of a plant, preferably after a period of drought, comprising applying a composition according to the invention to said plant.
    The present invention further relates to a method for increasing the recovery rate of a plant after a period of drought followed by rehydration, such as after episodic drought or rain after a long period of drought, including the application of of a composition according to the invention on said plant.
    BRIEF DESCRIPTION OF THE FIGURES
    Figure 1 is a graph showing the amount of proline in tomato leaves 24 hours after foliar application of oligoferulates at different concentrations. The values of the mean of the standard deviations are reported (n = 3).
    Figure 2 is a graph showing the percentage of germination of radish seeds 72 hours after treatment with oligoferatules for 30 minutes (3 repetitions, 20 seeds per repetition). The values of the mean of the standard deviations are reported (n = 3).
    Figure 3 is a graph showing the fresh weight of radish seedlings after 72 hours of seed germination treated with oligoferatules for 30 minutes (3 repetitions, 20 seeds per repetition). The values of the mean of the standard deviations are reported (n = 3).
    Figure 4 is a graph showing the percentage of germination of radish seeds, 4 days after treatment with a solution of 0.05 mM oligoferulates, a solution of 0.1% chitosan, or a solution comprising 0.05 mM oligoferulates and 0.1 % of chitosan (also called "Oligoferatics composition"), followed by dispersion on plates containing 50 ml of a 125 mM solution of mannitol to simulate osmotic stress conditions.
    Figure 5 is a photograph showing control wheat plants (left) and wheat plants treated with oligoferulae composition (treated, right) after seven days under simulated water stress (A) and one day after rehydration ( B).
    Figure 6 is a bar graph showing the fresh weight of control seedlings and wheat seedlings treated with an oligoferatase (treated) composition after seven days under simulated water stress followed by one day of rehydration. The values of the mean of the standard deviations are reported (n = 3). ANOVA tests indicate statistically significant differences (p <0.05) between plants treated with an oligoferulates composition and control solution.
    EXAMPLES
    The present invention is further illustrated by the following examples. In no case is the scope of the present invention limited by these examples.
    Example 1 Preparation of ferulic acid oligomers using a laccase as an enzyme
    A solution of 5 mM ferulic acid in methanol (50 mL) was added to 180 mL of ethyl acetate. After mixing, 200 mL of 1 U / mL laccase solution (Sigma-38429, Trametes versicolor laccase) in 50 mM sodium acetate buffer (pH 5.0) was added, and the reaction was performed at room temperature. 25 ° C for 24 hours with shaking on an orbital shaker at 150 rpm. At the end of the reaction, the organic phase was separated using a separatory funnel and the aqueous phase was washed twice with ethyl acetate. All ethyl acetate extracts were evaporated under reduced pressure using a rotary evaporator. The reaction products were redissolved in methanol and mass spectrometric analysis was performed as follows: 1 μL of the sample solution was placed on the spectrometer target and after drying, 1 μL of a DHB / matrix solution CH3CN was placed on the sample and after drying, the spectra were recorded on a Braker Ultraflex mass spectrometer (Braker Daltonik, Bremen, Germany) in the reflector mode using external calibration and working in the positive ion mode. The oliguferalate composition is shown in Table 1.
    Tail 1: Ion composition of the MALDI-TOF-MS spectra of the oligoferatas obtained by the enzymatic reaction using laccase
    * m / z represents the mass divided by the number of charges of the ions
    Example 2 Preparation of Ferulic Acid Oligomers Using a Peroxidase as an Enzyme
    A solution of 50 mM ferulic acid in methanol (200 mL) was added to a mixture of 400 mL of methanol, 80 mL of 0.3% hydrogen peroxide and 600 mL of 50 mM phosphate buffer (pH 7.0). ). After mixing, 10 mL of a 1% horseradish peroxidase solution (245.7 U / mg, AMRESCO INC) in 50 mM phosphate buffer (pH 7.0) was added and the reaction was carried out at 25 ° C. for 24 hours with shaking on an orbital shaker at 150 rpm. At the end of the reaction, the reaction mixture was filtered and the precipitate was washed twice with methanol. The methanol filtrate and the soluble phase of the reaction were evaporated under reduced pressure using a rotary evaporator.
    The reaction products were re-dissolved in methanol and TLC analysis was performed on silica gel plates (Merck 60 GF-254) using benzenediolane: acetic acid (25: 7: 1, v / v / v) as mobile phase. In addition, RP-HPLC analysis was performed using a Waters Symmetry C-18 column (46 x 250 mm) in a Waters Alliance 2695 separation module coupled with a Waters UV detector at 320 nm. The mobile phase consisted of a mixture of acetonitrile: 1% acetic acid (30:70) and the flow rate was 1 mL / min. Prior to injection, the samples were filtered through Sartorious filters (0.45 μm).
    Example 3: Foliar Spraying of Diferér Oligomers Increases Tomato Protein Content in a Dose-Response Model
    Materials and methods
    The tomato plants of the variety "Moneymaker" were cultivated for 3 weeks on soil under controlled conditions (light / darkness regime of 16 h / 8 h respectively, at 24 ° C). Formulations containing diferérulate at increasing concentrations and 0.01% Tween 80 (polysorbate 80) as an emulsifier were sprayed on the tomato leaves until runoff. 0.01% Tween 80 solution was used as a control. After 24 hours, the true leaves of the sprayed plants were collected and crushed in liquid nitrogen.
    Proline (Pro) has been estimated in tomato leaves according to Bates et al. (Plant and Soil, 1973, 39: 205-207) based on the reaction of proline with ninhydrin. A 500 mg sample of fresh leaves was homogenized in 5 ml of 3% aqueous sulphosalycylic acid and centrifuged at 22000g for 5 min. The supernatant was filtered through Sartorious filters (0.45 μm). To 1 mL of the filtrate, 1 mL of ninhydrin reagent (2.5 g of ninhydrin / 100 mL of a solution containing glacial acetic acid, distilled water and 85% orthophosphoric acid a ratio of 6: 3: 1) was added and boiled in a water bath at 100 ° C for 1 h. The readings were taken immediately at a wavelength of 546 nm. The pro line concentration was determined from a standard curve using proline (sigma) and calculated on the basis of fresh weight (mmol proline, g FW-1). Results
    The results presented in Figure 1 show that at low concentrations, the oligomers of diférulates allow the control of Pro content in plants and that it follows a positive linear correlation in relation to the doses applied (dose-response).
    ANOVA tests indicate statistically significant differences (p <0.05) between treated plants with the formulation and with the control solution containing Tween 80.
    Since proline accumulation in plants is known to have both osmoprotective and antioxidant functions, the results show that diférulate oligomers improve osmoprotection and protection against oxidative damage to the plant.
    Example 4 Treatment of radish seeds with oligoferulas increases germination rate and seedling growth
    Materials and methods
    Radish seeds (Raphanus sativus) of the Ronde rode variety were incubated for 30 minutes in a solution of 15 ppm oligoferatas or water (control). The test was repeated 3 times for each treatment, 20 seeds per repetition. The seeds were then dried and placed in an incubator at 30 ° C for optimal germination in water, without stress. After 3 days, sprouted seeds were counted and radish seedlings collected and weighed. Results
    The results show that radish seeds treated with oligoferulas have about 15% more germination percentage than the control where the seeds were incubated with water (62% of germination for control, 77% for germination for control, seeds treated with oligoferatas, Figure 2).
    Similarly, seedling seedlings treated with oligoferulas grew more rapidly by about 14% compared to untreated seeds (0.49 g fresh weight for control, 0.56 g for seeds treated with oligoferatas; 3).
    These results show that oligoferulas are able to modify the behavior of the plant even under non-stressful conditions.
    EXAMPLE 5 Treatment of radish seeds with oligoferulas or with a composition comprising oligoferulates and chitosan to improve the germination of plants under stress conditions
    Materials and methods
    Radish seeds (Raphanus sativus) of the Ronde rode variety were incubated for 5 min in water (as a control), in a solution of oligoferulates at 0.05 mM, a solution of chitosan at 0.1%, or a solution comprising 0.1% chitosan and 0.05 mM oligoferulates (solution then called "Oligoferatum composition"). After drying, the coated seeds were dispersed on plates containing 50 ml of a 125 mM mannitol solution to induce osmotic stress conditions. The plates were sealed with Parafilm M® to prevent dehydration and allowed to incubate at 30 ° C. After 4 days, sprouted seeds were counted and the percentage of germination calculated. Results
    The results show that radish seeds pretreated with a solution comprising oligoferulates alone significantly increased the percentage of germination of radish seeds under stress conditions (52% germinated seed seeds treated with oligoferulates and 23% sprouted seeds). control) (Figure 4).
    On the other hand, radish seeds treated exclusively with chitosan show a germination percentage comparable to control seeds (21% sprouted seeds for chitosan-treated seeds) (Figure 4).
    Moreover, the radish seeds pretreated with a solution comprising oligoferulates and chitosan (oligoferatum composition) show a very significant increase in the percentage of germination compared to the control, with 68% of sprouted seeds (FIG. 4).
    These results reveal that the application of oligoferuates, or better yet an oligoferulate composition (oligoferulates and chitosan), shows increased plant germination compared to control or chitosan alone.
    Example 6: The coating of seeds with an oligoferulus composition induces a tolerance to water stress in wheat plants.
    Materials and methods
    Seeds of wheat plants were coated with a composition comprising 0.005% diférulate and 0.5% chitosan (hereinafter referred to as "oligoferulates composition"), and water (as a control). After drying, six wheat seeds per pot (3 pots per treatment) were planted and cultivated for 3 weeks on soil under controlled conditions (light / darkness regime of 16 h / 8 h respectively at 24 ° C). At that time, irrigation was suspended, and no water was added to simulate a drought stress situation. After seven days under this condition, the irrigation was restored, mimicking drought or rain after a long period of drought. The recovery capacity of the plants was estimated the next day, based on the total weight of the wheat plants. Results
    The results show that this intense drought stress has irreversibly injured the tissue of the untreated plants (control, Figures 5A and 5B left, and Figure 6), while the plants treated with the oligoferapid composition show a particularly high recovery (treated Figures 5A and 5B right, and Figure 6).
    As a result, the oligoferula composition can help plants to better respond to episodes of drought or episodic rainfall which is remarkably useful for implementing vegetation management practices under changing climatic conditions.
    权利要求:
    Claims (15)
    [1]
    A composition for improving the stress tolerance of a plant, wherein said composition comprises at least one oligomer of hydroxycinnamic acid derivative.
    [2]
    The composition of claim 1, wherein said at least one hydroxycinnamic acid derivative oligomer has a degree of polymerization of at least two.
    [3]
    The composition of claim 1 or 2, wherein said at least one hydroxycinnamic acid derivative is selected from the group consisting of ferulic acid, p-coumaric acid, caffeic acid and sinapinic acid.
    [4]
    4. Composition according to any one of claims 1 to 3, wherein said composition comprises at least one oligomer of ferulic acid, preferably diferulic acid.
    [5]
    The composition of any one of claims 1 to 4, wherein said composition comprises from 0.0001 to 200 ppm of said at least one hydroxycinnamic acid derivative oligomer, preferably from 0.001 to 100 ppm, more preferably from 0.005 to 50. ppm.
    [6]
    A composition according to any one of claims 1 to 5, wherein said composition comprises at least 10% hydroxycinnamic acid derivative dimer, expressed as a percentage based on total hydroxycinnamic acid derivative oligomers of the composition. preferably at least 20%, more preferably at least 30%.
    [7]
    The composition of any one of claims 1 to 6, wherein the stress is abiotic or biotic.
    [8]
    The composition of claim 7, wherein said abiotic stress is selected from the group consisting of water stress, drought, osmotic stress, heat stress, nutrient deficiency, and chemical stress generated by a metal pollutant or in the soil in which said plant grows, preferably water stress, dryness or osmotic stress.
    [9]
    9. Composition according to any one of claims 1 to 8, further comprising at least one solubilizing agent in water.
    [10]
    The composition of claim 9, wherein said at least one solubilizing agent in water is selected from the group consisting of polysaccharides and polyols.
    [11]
    The composition of claim 9 or 10, wherein said at least one solubilizing agent in water is a polysaccharide selected from the group consisting of chitosan, chitin, chitin-glucan, carboxymethylcellulose, pectin, hemicellulose, preferably chitosan.
    [12]
    A leaf sprayer comprising a composition according to any one of claims 1 to 11.
    [13]
    13. A plant seed, wherein said seed is coated with a composition according to any one of claims 1 to 11.
    [14]
    14. Use of a composition comprising at least one hydroxycinnamic acid derivative oligomer for improving the stress tolerance of a plant, comprising applying a composition according to any one of claims 1 to 11 to said plant .
    [15]
    A method for improving the tolerance of a plant to stress comprising applying a composition according to any one of claims 1 to 11 to said plant.
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    同族专利:
    公开号 | 公开日
    AR107213A1|2018-04-11|
    MA42809A|2021-05-12|
    ZA201802299B|2020-10-28|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    EP15185212|2015-09-15|
    EP15185212.6|2015-09-15|CN201680060504.XA| CN108347931A|2015-09-15|2016-09-15|Bioactive composition for improving stress tolerance in plants|
    PCT/EP2016/071810| WO2017046237A1|2015-09-15|2016-09-15|Bioactive composition for improving stress tolerance of plants|
    MX2018003158A| MX2018003158A|2015-09-15|2016-09-15|Bioactive composition for improving stress tolerance of plants.|
    RU2018113337A| RU2751596C2|2015-09-15|2016-09-15|Composition containing oligomer of hydroxycinnamic acid derivative, use thereof, device, seeds, method for increasing tolerance to plant stress, method for modulating proline content in plants|
    EP16766005.9A| EP3349578A1|2015-09-15|2016-09-15|Bioactive composition for improving stress tolerance of plants|
    AU2016324974A| AU2016324974B2|2015-09-15|2016-09-15|Bioactive composition for improving stress tolerance of plants|
    US15/760,468| US20180242579A1|2015-09-15|2016-09-15|Bioactive composition for improving stress tolerance of plants|
    MA042809A| MA42809A|2015-09-15|2016-09-15|BIOACTIVE COMPOSITION ENABLING TO IMPROVE THE TOLERANCE TO STRESS OF PLANTS|
    CL2018000683A| CL2018000683A1|2015-09-15|2018-03-15|Bioactive composition to improve plant stress tolerance|
    ZA2018/02299A| ZA201802299B|2015-09-15|2018-04-09|Bioactive composition for improving stress tolerance of plants|
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