Methods for improving plant growth, development and resistance to abiotic / biological stress

Abstract

The present invention relates to methods for improving plant growth, development and / or resistance to abiotic / biological stress.

Description

TECHNICAL FIELD

[0001] The present invention relates to a method for improving growth, development and / or resistance to abiotic stress / biotic stress of a plant. BACKGROUND

[0002] The agricultural industry faces multiple challenges, including producing enough food and fiber to meet the needs of a growing global population, adopting more efficient and sustainable production methods, and adapting to climate change.

[0003] Abiotic stresses, such as frost or drought, are major problems in the agricultural industry, as plants are not always able to adjust properly to cold, drought, osmotic stress (e.g. salinization), heat, etc. Plants are particularly dependent on environmental factors and cannot actively change location, and are therefore particularly vulnerable to abiotic stress. Abiotic stress is the most important factor that negatively affects global crop growth and yield. For example, drought stress is one of the main reasons for crop yield reduction in the agricultural sector. Likewise, frost can also significantly cause crop yield reduction, at least in areas where the temperature is not above freezing throughout the year.

[0004] In addition, plants are also subject to attack by pests, such as fungi, molluscs, viruses, insects, etc. These pests can cause damage to plants and can induce plant diseases. This can lead to crop yield reduction and contamination of agricultural products. There are a large number of chemical pesticides available, but they have been rigorously reviewed, as chemical pesticides have many negative effects on health, with high occupational, intentional or accidental exposure potentially leading to hospitalization or death, and exposure routes being through skin contact, ingestion of contaminated consumables or inhalation, whereby chemical pesticides can be metabolized, excreted, stored or accumulated in body fat (Nicolopoulou-Stamati et al., 2016, Front. Public Health 4 (148)). Ideal pesticides should not only be harmless to human health, but also be environmentally friendly and as efficient and specific as possible in protecting plants against specific pests. In addition, ideal pesticides should also avoid the development of resistance by pests. There is still a need to develop new products that meet these criteria.

[0005] The present invention therefore relates to the growth and development of plants, and to the protection of said plants against abiotic stress and biotic stress. SUMMARY

[0006] Surprisingly, it was found that sialic acid-containing saccharides can improve the growth, development and / or resistance to abiotic stress and / or biotic stress of a plant, wherein the degree of polymerization (DP) of the sialic acid-containing saccharides is at least 2.

[0007] Therefore, a first aspect of the present invention provides a plant treatment method, wherein a sialic acid-containing sugar is applied to the plant, a portion of the plant, the seeds of the plant, and / or the intended growth area of ​​the plant, wherein the degree of polymerization (DP) of the sialic acid-containing sugar is at least 2. A second aspect of the present invention provides the use of sialic acid-containing sugars as plant growth and / or plant development biostimulants, wherein the degree of polymerization (DP) of the sialic acid-containing sugars is at least 2. A third aspect of the present invention provides the use of sialic acid-containing sugars as plant protectants, wherein the degree of polymerization (DP) of the sialic acid-containing sugars is at least 2. Detailed Implementation

[0008] Plant treatment method A first aspect of the present invention provides a plant treatment method comprising applying a sialic acid-containing sugar to said plant, a portion of said plant, seeds of said plant, and / or a desired growth area of ​​said plant, wherein said sialic acid-containing sugar has a degree of polymerization (DP) of at least 2. The inventors have unexpectedly discovered that the method according to the invention provides several advantages to plants (compared to untreated plants), including: (i) promoted growth; (ii) promoted development; (iii) protected plants against abiotic stresses and / or (iv) protected plants against biotic stresses, as described herein. Furthermore, the method according to the invention significantly improves flower development and flower protection, even under abiotic stresses such as frost.

[0009] In this application and claims, the expression "applying sialic acid-containing sugars to the plant, parts of the plant, seeds of the plant and / or the intended growth area of ​​the plant" is preferably replaced with the expression "applying sialic acid-containing sugars to the plant, parts of the plant and / or seeds of the plant".

[0010] For the purposes of this invention, and as understood by those skilled in the art, a sugar with a degree of polymerization (DP) of at least 2 means a sugar containing at least 2 monosaccharides.

[0011] For the purposes of this invention, the term "treatment" should be interpreted broadly, that is, the application of a substance (in the context of this invention, the substance is a sialic acid-containing sugar, optionally one or more additional sugars) to a plant, a part of the plant, the seeds of the plant, and / or the intended growth area of ​​the plant. Numerous methods of substance delivery are known to those skilled in the art, and depending on whether the substance needs to be delivered to the plant, a part of the plant, the seeds of the plant, and / or the intended growth area of ​​the plant, those skilled in the art can readily select a suitable method of application based on their general common sense (e.g., Gahukar, 2016, Phytoparasitica 44(3), pp. 379-391).

[0012] For the purposes of this invention, the term "region" preferably refers to soil, inert substrate, volcanic debris, synthetic organic substrate (e.g., polyurethane), organic substrate (e.g., peat, compost, wood waste such as coconut fiber, wood fiber or sawdust, bark), liquid substrate (e.g., floating hydroponic systems), aeroponics, and hydroponics (e.g., nutrient film membrane technology). The inert substrate includes inorganic substrates (e.g., sand, rock wool, glass wool) and expanded minerals (e.g., perlite, vermiculite, zeolite, expanded clay). More preferably, the region refers to soil.

[0013] For the purposes of this invention, the term "plant part" refers to any part of a plant, including roots, stems, leaves, petioles, flowers, fruits, and seeds. Preferably, the plant part is the above-ground part of the plant, i.e., the part above the soil. Therefore, the plant part is more preferably selected from a list consisting of seeds, leaves, petioles, flowers, fruits, and stems, more preferably selected from a list consisting of seeds, leaves, flowers, and fruits, and more preferably seeds or leaves. For clarity, grain is an example of a seed derived from grasses (e.g., wheat, oats, rice, sorghum, millet, rye, barley, corn). Those skilled in the art will know that plants can contain tubers, which are storage containers for nutrients. For clarity, root tuber is an example of a root, while stem tuber is an example of a stem. Since the plant part is preferably the above-ground part of the plant for the purposes of this invention, the stem is also preferably not to include stem tubers for the purposes of this invention, as it is the part below the soil.

[0014] In a preferred embodiment of the invention, as described in this application and claims, the step of applying the sugar (i.e., the sialic acid-containing sugar of the present invention, optionally one or more additional sugars) includes one or more selected from watering, spraying (including ultra-low volume spraying), irrigation, atomizing, nebulizing, dusting, foaming, spreading, coating, drenching, dripping, and injection; preferably, it is carried out by watering, spraying (including ultra-low volume spraying), irrigation, atomizing, nebulizing, dusting, foaming, spreading, coating, drenching, dripping, or injection (e.g., trunk injection, soil injection). The scope of this invention also covers situations where the step of applying sugars involves one or more application methods, preferably selected from one or more of the following: watering, spraying (including ultra-low volume spraying), irrigation, atomization, spraying, dusting, foaming, spreading, coating, drenching, drip irrigation, and injection (e.g., trunk injection, soil injection). In this application and claims, coating is preferably performed by spraying.

[0015] For seed application (as described below), coating is particularly preferred over any other application technique, especially irrigation and soaking. Therefore, in this application and claims, seed application by coating is particularly preferred, and coating by spraying is more preferred.

[0016] The purpose of seed coating (especially by spraying) is to ensure that the substance(s) adhere to the outside of the seed. Adhesives are typically used to assist in achieving this. Furthermore, seed coating (especially by spraying) allows for the application of a predetermined and precise dosage to the seed, which is not possible with irrigation or soaking, where it is impossible to know how much the seed will absorb. Moreover, seed coating (especially by spraying) prevents prolonged contact with liquid, which inevitably initiates a pre-germination process (as is the case with irrigation, for example).

[0017] In additional and / or alternative preferred embodiments, in this application and claims, the step of applying the sugar (i.e., the sialic acid-containing sugar of the present invention, optionally one or more additional sugars) is seed application, root application, aerial application, or soil application, preferably seed application or aerial application. The scope of the invention also covers situations where the step of applying the sugar involves one or more applications selected from the list of seed application, root application, aerial application, or soil application. The term "aerial application" refers to applying a substance (in the context of the invention, i.e., sialic acid-containing sugar, optionally one or more additional sugars) to one or more parts of the plant above the soil (including stems, leaves, petioles, flowers, fruits, and seeds). Preferably, aerial application is applying a substance (in the context of the invention, i.e., sialic acid-containing sugar, optionally one or more additional sugars) to stems, leaves, petioles, flowers, fruits, or seeds; more preferably, to stems, leaves, flowers, or seeds; and most preferably, to leaves or seeds. For stem application, application to tubers is particularly preferred.

[0018] In this application and claims, the term "root application" preferably refers to the application of the sugars (optionally, one or more additional sugars) to the exterior of the root, and therefore preferably excludes the application of the sugars (optionally, one or more additional sugars) to the interior of the root. Similarly, in this application and claims, "the application of the sugars (optionally, one or more additional sugars) to a portion of the plant, wherein the portion is the root," preferably refers to the application of the sugars (optionally, one or more additional sugars) to the exterior of the root of the plant, and therefore preferably excludes the application of the sugars (optionally, one or more additional sugars) to the interior of the root. In this application and claims, the term "exterior of the root" is preferably replaced with "root epidermis."

[0019] In this application and claims, the term "stem application" preferably refers to the application of the sugar (optionally, one or more additional sugars) to the exterior of the stem, and therefore preferably excludes the application of the sugar (optionally, one or more additional sugars) to the interior of the stem. Similarly, in this application and claims, "the application of the sugar (optionally, one or more additional sugars) to a portion of the plant, wherein the portion is the stem," preferably refers to the application of the sugar (optionally, one or more additional sugars) to the exterior of the stem of the plant, and therefore preferably excludes the application of the sugar (optionally, one or more additional sugars) to the interior of the stem.

[0020] In a more preferred embodiment, in this application and claims, the step of applying the sugar (i.e., the sialic acid-containing sugar of the present invention, optionally one or more additional sugars) is seed application, foliar application, stem application, root application, air application, or soil application, preferably seed application, foliar application, or stem application, more preferably seed application or foliar application. The scope of the invention also covers situations where the step of applying the sugar includes one or more applications selected from the list consisting of seed application, foliar application, stem application, root application, and soil application. Furthermore, it should be noted that stem application includes applying the sugar described herein to the bulb (i.e., the food storage organ present in ornamental bulbous plants).

[0021] With regard to the method of the present invention for protecting plants against biotic stress (see the section on “Abiotic Stress and / or Biological Stress”), the step of applying sugars (i.e., the sugars of the present invention containing sialic acid, optionally one or more additional sugars) is most preferably applied by seed.

[0022] With respect to this invention, the sialic acid-containing sugar of this invention can be applied once to the plant, a part of the plant, the seeds of the plant, and / or the intended growth area of ​​the plant; or it can be applied multiple times. The multiple applications can be performed on the same day, but preferably on different dates, with an interval of at least one day, more preferably at least two days, and even more preferably at least one week between two consecutive applications of the sialic acid-containing sugar of this invention.

[0023] In a particularly preferred embodiment of the method of the present invention, the sialic acid-containing sugar of the present invention is applied once to the plant, a portion of the plant, the seeds of the plant, and / or the intended growth area of ​​the plant.

[0024] With regard to the method of the present invention, preferably for the method of protecting plants against abiotic and / or biotic stress (see the section on "Abiotic and / or Biological Stress"), more preferably for the method of protecting plants against abiotic stress (see the section on "Abiotic and / or Biological Stress"), the sialic acid-containing sugar of the present invention is applied at least 1 day, preferably at least 2 days, more preferably at least 3 days, more preferably at least 4 days, and most preferably at least 5 days before exposure to said abiotic and / or biotic stress (preferably abiotic stress). More preferably, the sialic acid-containing sugar of the present invention is applied ≤8 weeks, preferably ≤7 weeks, more preferably ≤6 weeks, more preferably ≤5 weeks, more preferably ≤4 weeks, more preferably ≤3 weeks, and most preferably ≤2 weeks before exposure to said abiotic and / or biotic stress (preferably abiotic stress). More preferably, the sugar containing sialic acid of the present invention is applied 1-42 days, preferably 1-35 days, more preferably 2-35 days, more preferably 3-35 days, more preferably 3-28 days, more preferably 3-21 days, more preferably 3-21 days, more preferably 3-14 days, more preferably 5-14 days, and most preferably 5-10 days before exposure to the abiotic stress and / or biotic stress (preferably abiotic stress).

[0025] With regard to the method of the present invention, the preferred method is for protecting plants or parts of plants (preferably flowers or fruits) against abiotic and / or biotic stresses (see the section on "Abiotic and / or Biological Stresses"), more preferably for protecting plants or parts of plants (preferably flowers or fruits) against abiotic stresses (see the section on "Abiotic and / or Biological Stresses"), and another preferred embodiment is the application of the sialic acid-containing sugars of the present invention before the flowering stage (i.e., before stage 6 in the BBCH classification), more preferably during the inflorescence germination stage (i.e., stage 5 in the BBCH classification). The BBCH (Biologische Bundesanstalt, Bundessortenamt and Chemical industry, German Federal Research Center for Biology, German Federal Office for Variety Development and Chemical Industry) classification is a widely used system for uniformly identifying the phenological developmental stages of plants (BBCH Monograph, Growth stages of mono- and dicotyle-donous plants, Julius Kühn-Institut, ISBN 978-3-95547-071-5).

[0026] Plant In a preferred embodiment of the first aspect of the invention, the plant is a cultivable crop, a fruiting plant, or a vegetable.

[0027] The arable crops are preferably selected from the list consisting of grain crops, pulse crops, oilseed crops, forage crops, fiber crops, and tuber crops; more preferably, from the list consisting of grain crops, oilseed crops, and tuber crops; even more preferably, grain crops or oilseed crops. Grain crops are generally grown for their edible starchy grains. Preferred examples include maize (i.e., corn), wheat (winter and spring wheat), rice, barley, oats, millet, sorghum, rye, spelt, durum, triticale, and sugarcane. More preferred examples include maize, wheat (winter and spring wheat), rice, barley, oats, millet, rye, spelt, durum, triticale, and sugarcane. Even the most preferred examples include maize, wheat (winter and spring wheat), and barley. Throughout this application and claims, unless otherwise expressly stated, the terms "corn" and "maize" are used interchangeably. Legume crops are typically grown for their high-protein, edible seeds. Preferred examples include lentils, beans (e.g., green beans, French beans, runner beans, haricot beans, lima beans), soybeans, broad beans, and peas (e.g., peas, snap peas, snowpeas, splitpeas). More preferred examples include soybeans and broad beans. Oilseed crops are typically grown for the extraction of oil from their seeds. Preferred examples include rapeseed, soybeans, sunflowers, cotton, canola, and peanuts. Forage crops are typically grown to feed animals. Preferred examples include cowpea, clover, and timothy. Fiber crops are typically grown for non-food purposes. Preferred examples include cotton, jute, flax, coir, and hemp. Tuber crops are typically grown for their edible underground parts. Preferred examples include potato, yam, cassava, and araceae plants. More preferred examples include potato.

[0028] More preferably, the arable crops are cereal crops.

[0029] The selected plants were preferably chosen from the following list: Abiu (golden gooseberry), almond, Amla (Indian gooseberry), apple, apricot, avocado, banana, bael (orange), ber (Indian plum), capsicum annuum (e.g., pepper, bell pepper, sweet pepper), carambola (starfruit), cashew, cherry, citrus (clementine, lemon, lime, orange, etc.), coconut, crabapple. Apple, plum (Damson), durian, elderberry, grapefruit, guava, jackfruit, jujube, loquat, lychee, mango, medlar, Morello cherry, mulberry, olive, papaya, carica papaya, asimina triloba, peach, nectarine, pear, pecan, persimmon, pineapple, plum, pomelo, quince, pomegranate, rambutan, sapodilla (chikoo), soursop, strawberry, sugar-apple (sharifa), sweet chestnut, tamarillo, tomato, Ugli fruit, walnut, water apple, coffee, and grape; more preferably, a list consisting of apple, cherry, Morelo cherry, mulberry, olive, pear, strawberry, coffee, and grape; more preferably, a list consisting of apple, cherry, strawberry, coffee, and grape; more preferably, a list consisting of apple, cherry, strawberry, and grape.

[0030] The preferred vegetables are legumes, and more preferably from the following list: *Brassica oleracea* (e.g., cabbage, Brussels sprouts, cauliflower, broccoli, kale, kohlrabi, red cabbage, Savoy cabbage, Chinese broccoli, collardgreens), *Brassica rapa* (e.g., turnip, Chinese cabbage, napa cabbage, bok choy), *Raphanus sativus* (e.g., radish, daikon, seedpod varieties), *Daucus carota* (e.g., carrot), *Pastilbena sativa* (e.g., parsnip), *Beta vulgaris* (e.g., beetroot, sea beet, Swiss chard, sugar beet), and *Lactuca*. (e.g., lettuce, celtuce), asparagus (e.g., asparagus), green beans (Phaseolus vulgaris), broad beans (Phaseoluscoccineus), cotton beans (Phaseolus lunatus) (e.g., green beans, French beans, red beans, lentils, lima beans), broad beans (Vicia faba) (e.g., broad beans), peas (Pisum sativum) (e.g., peas, snap peas, snow peas, split peas), potatoes (Solanum tuberosum) (e.g., potatoes), eggplants (Solanum melongena) (e.g., eggplant), tomatoes (Solanum lycopersicum) (e.g., tomatoes), cucumbers (Cucumis sativus) (e.g., cucumbers), and species of the genus Cucurbita (Cucurbita spp.).(e.g., large pumpkin, small pumpkin, zucchini, dense zucchini, gourd), onion (Allium cepa) (e.g., onion, scallion, green onion), garlic (Allium sativum) (e.g., garlic), Southern European garlic (Allium ampeloprasum) (e.g., leek, elephant garlic), pepper (Capsicum annuum) (e.g., pepper, bell pepper, sweet pepper), spinach (Spinacia oleracea) (e.g., spinach), Dioscorea species (e.g., yam), sweet potato (Ipomoea batatas) (e.g., sweet potato), and cassava (Manihot esculenta) (e.g., cassava); more preferably, a list consisting of broad beans (Vicia faba) (e.g., broad bean), peas (Pisumsativum) (e.g., pea, crisp pea, snow pea, split-pod pea), and potatoes (e.g., potato); most preferably, potatoes.

[0031] In a more preferred embodiment, the plant is selected from the list consisting of: maize; cotton; cereals, including wheat (winter and spring wheat), spelt wheat, durum wheat, rye, barley, oats, millet, and triticale; rapeseed as used herein includes European rapeseed (Brassica napus subsp napus), also known as Argentine canola, rapeseed, or rape, and specific groups of cultivated varieties, canola; turnip (Brassica rapa), also known as Polish canola, and mustard (Brassica juncea), also known as quality canola brown. mustard; the perennials used in this article include coffee, sugarcane; fruiting plants, such as golden cherries, almonds, currants (Indian currants), apples, apricots, avocados, tangerines, jujubes (Indian plums), star fruit, cashews, cherries, citrus fruits (Clementia spp., lemons, limes, oranges, etc.), coconuts, crabapples, plums, durians, elderberries, figs, grapefruits, guavas, jackfruits, dates, loquats, lychees, mangoes, hawthorns, Morelo cherries, mulberries, olives, and papayas (tropical papayas (Carica papaya) and North American trifoliate papayas (Asimina)). Triloba), peaches and nectarines, pears, pecans, persimmons, plums, pomelos, quince, pomegranates, rambutans, sapodilla (chicory), custard apple, strawberries, custard apple (sugar apple), chestnuts, tree tomatoes, Jamaican ugly oranges, walnuts, rose apples and grapes; rice; sorghum, soybeans; turfgrass; vegetables, including wild cabbage (Brassica oleracea) (such as cabbage, Brussels sprouts, cauliflower, broccoli, kale, kohlrabi, red cabbage, crouton, Chinese kale, onion cabbage), turnip (Brassica rapa) (such as turnips, Chinese cabbage, bok choy), radishes (Raphanus sativus) (such as water radishes, white radishes, crisp radish varieties), wild carrots (Daucus carota) (such as carrots);European parsnip (Pastina casativa) (e.g., parsnip), beet (Beta vulgaris) (e.g., beetroot, sea beet, Swiss chard, sugar beet), lettuce (Lactuca sativa) (e.g., lettuce, romaine lettuce), asparagus (Aspargus officinalis) (e.g., asparagus), green bean (Phaseolus vulgaris), broad bean (Phaseolus coccineus), and cotton bean (Phaseolus lunatus) (e.g., green bean, French bean, red bean, lentil, lima bean), broad bean (Vicia faba) (e.g., broad bean), pea (Pisum sativum) (e.g., pea, crisp bean, snow pea, split pea), potato (Solanum tuberosum) (e.g., potato), eggplant (Solanum melongena) (e.g., eggplant), tomato (Solanum lycopersicum) (e.g., tomato), cucumber (Cucumis) *Sativus* (e.g., cucumber), *Cucurbita* spp. (e.g., large-fruited squash, small-fruited squash, zucchini, densely packed zucchini, bottle gourd), *Allium cepa* (e.g., onion, scallion, green onion), *Allium sativum* (e.g., garlic), *Allium ampeloprasum* (e.g., leek, elephant garlic), *Capsicum annuum* (e.g., pepper, bell pepper, sweet pepper), *Spinacia oleracea* (e.g., spinach), *Dioscoreas* pp. (e.g., yam), *Ipomoea batatas* (e.g., sweet potato), and *Manihot esculenta* (e.g., cassava).

[0032] In a more preferred embodiment, the plants are selected from the list of the following: corn; cotton; cereals, including wheat (winter wheat and spring wheat), spelt wheat, durum wheat, rye, barley, oats, millet, and triticale; rapeseed as used herein includes European rapeseed, also known as Argentine rapeseed, canola, or rapeseed; perennial plants as used herein include coffee; sugarcane; fruiting plants such as apple, cherry, Morelo cherry, mulberry, olive, pear, strawberry, and grape; rice, soybean; broad bean (Vicia faba) (e.g., broad bean); pea (Pisum sativum) (e.g., pea, crisp bean, snow pea, split pea) and potato (e.g., potato).

[0033] In a more preferred embodiment, the plants are selected from the list of the following: corn; cotton; cereals, including wheat (winter wheat and spring wheat) and barley; rapeseed, including European rapeseed; perennial plants, including coffee; sugarcane; fruiting plants, such as apple, cherry, strawberry and grape; soybean and potato (such as potato).

[0034] In another preferred embodiment, the plant is under physiological conditions, abiotic stress, or biotic stress. In this invention, the terms "physiological conditions" and "normal conditions" are used interchangeably, preferably referring to conditions typically used for cultivating the plant, although those skilled in the art will understand that these conditions may vary depending on the plant species. More preferably, the physiological conditions refer to conditions where neither abiotic nor biotic stress exists. The terms "abiotic stress" and "biotic stress" are preferably used as described in the section on "Abiotic Stress and / or Biological Stress".

[0035] Sialic acid-containing saccharides In one embodiment of the first aspect of the invention, the method includes the step of applying a sialic acid-containing sugar to the plant, a portion of the plant, the seeds of the plant, and / or the intended growth area of ​​the plant, wherein the degree of polymerization (DP) of the sialic acid-containing sugar is at least 2.

[0036] Those skilled in the art will understand that the term "carbohydrate" refers to a molecule containing at least one monosaccharide, preferably a molecule composed of one or more monosaccharide residues. As used herein, the term "monosaccharide" refers to a sugar that cannot be hydrolyzed into simpler sugars, is classified as an aldose or ketose, and each molecule contains one or more hydroxyl groups. Therefore, a monosaccharide is a carbohydrate containing only one simple sugar.

[0037] Therefore, for the purposes of this invention, "a sugar containing sialic acid with a degree of polymerization (DP) of at least 2" means a sugar containing at least two monosaccharides, wherein at least one monosaccharide is sialic acid.

[0038] The terms “sialic acid-containing sugars” and “sialylated sugars” are used interchangeably in this document to refer to sugars containing sialic acid, that is, sugars containing one or more sialic acid residues.

[0039] The sialic acid preferably has a nine-carbon skeleton (i.e., nine-carbon sialic acid) or an eight-carbon skeleton (i.e., eight-carbon sialic acid), more preferably a nine-carbon skeleton. Sialic acids with a nine-carbon skeleton are well known to those skilled in the art, referring to a group of monosaccharides derived from an acidic nine-carbon parent compound—N-acetylneuraminic acid (Neu5Ac) or 2-keto-3-deoxynonanoic acid (Kdn; the deamination form of N-acetylneuraminic acid)—through modifications such as the addition of acetyl, phosphate, methyl, sulfate, and / or lactate groups. Furthermore, the N-acetyl group of Neu5Ac can be hydroxylated to generate N-hydroxyacetylneuraminic acid (Neu5Gc). More than 50 different examples of sialic acids with a nine-carbon skeleton are known (Essentials of Glycobiology, 2nd edition, 2009, Chapter 14, Varki and Schauer). Sialic acid with an eight-carbon skeleton is structurally related to sialic acid with a nine-carbon skeleton, particularly to Kdn (Essentials of Glycobiology, 2nd ed., 2009, Chapter 14, Varki and Schauer). Therefore, the term "sialic acid with an eight-carbon skeleton" is preferably replaced with "octanoic acid 2-keto-3-deoxyoctanoic acid".

[0040] In a preferred embodiment, the sialic acid-containing sugar comprises nine-carbon sialic acid, preferably selected from the list of the following: Neu5Ac; Neu4Ac; Neu4,5Ac2; Neu5,7Ac2; Neu5,8Ac2; Neu5,9Ac2; Neu4,5,9Ac3; Neu5,7,9Ac3; Neu5,8,9Ac3; Neu4,5,7,9Ac4; Neu5,7,8,9Ac4; Neu4,5,7,8,9Ac5; and Neu5Gc; more preferably, the nine-carbon sialic acid is N-acetylneuraminic acid (i.e., Neu5Ac). In this application and claims, the term "nine-carbon sialic acid" is preferably replaced with "N-acetylneuraminic acid (Neu5Ac)".

[0041] In additional and / or alternative preferred embodiments, the sialic acid-containing sugar comprises octose sialic acid, preferably ketodeoxyoctanoic acid (KDO; i.e., 2-keto-3-deoxy-D-mannulocylic acid, also known as 2-oxo-3-deoxy-D-mannulocylic acid, 3-deoxy-D-mannuno-2-ketogonic acid, 3-deoxy-D-mannuno-2-octulose or 3-deoxy-D-mannuno-2-keto-pyranose). In this application and claims, the term "octose sialic acid" is preferably replaced with "octose 2-keto-3-deoxyoctanoic acid," and more preferably with "ketodeoxyoctanoic acid (KDO)."

[0042] For the purposes of this invention, sialic acid-containing sugars according to the invention may comprise: (i) one or more 9-carbon sialic acids; (ii) one or more 8-carbon sialic acids; or (iii) one or more 9-carbon sialic acids and one or more 8-carbon sialic acids. Unless otherwise expressly stated, in this application and claims, more preferably, sialic acid-containing sugars according to the invention comprise 9-carbon sialic acids, and preferably, said sugars do not contain 8-carbon sialic acids. In other words, unless otherwise expressly stated, in this application and claims, more preferably, sialic acid-containing sugars according to the invention comprise one or more 9-carbon sialic acids, and preferably, said sugars do not contain 8-carbon sialic acids. Therefore, when the list of sugars listed herein contains both sugars containing 9-carbon sialic acids and sugars containing 8-carbon sialic acids, the absence of an identical list of sugars not containing 9-carbon sialic acids is also explicitly and unambiguously disclosed herein.

[0043] In additional and / or alternative preferred embodiments, the sialic acid-containing sugars of the present invention are disaccharides or oligosaccharides. For the purposes of this invention, the term "oligosaccharide" preferably refers to a sugar containing 2 to 20 (inclusive) monosaccharides, i.e., a degree of polymerization (DP) of 2-20. Oligosaccharides can be linear or branched. The bonding between two sugar units (e.g., glycosidic, galactosidic, glucosidic, etc.) can be represented, for example, 1,4, 1->4, or (1-4), and these representations are used interchangeably herein. Each monosaccharide can be cyclic (e.g., pyranose or furanose). Oligosaccharides can contain both α-glycosidic and β-glycosidic bonds, or only β-glycosidic bonds.

[0044] In a more preferred embodiment, the sialic acid-containing sugar comprises sialic acid (preferably the sialic acid disclosed above herein, more preferably Neu5Ac), which is linked to a monosaccharide via an α-2,3-, α-2,6-, or α-2,8- bond, preferably via an α-2,3- or α-2,6- bond, more preferably via an α-2,6- bond, and wherein the monosaccharide is preferably selected from galactose, N-acetylglucosamine, and sialic acid (preferably Neu5Ac), more preferably, the monosaccharide is galactose or N-acetylglucosamine, and more preferably, the monosaccharide is galactose. Those skilled in the art will understand that the expression "sialic acid linked to a monosaccharide" means that the sialic acid is combined with the monosaccharide via a glycosidic bond, and wherein the sialic acid and the monosaccharide are part of the sugars of the present invention (the sugars of the present invention may contain one or more additional monosaccharides in addition to the sialic acid and the monosaccharide, and may contain one or more additional sialic acids).

[0045] In additional and / or alternative preferred embodiments, the sialic acid-containing sugar according to the present invention is a disaccharide or an oligosaccharide. In a more preferred embodiment, the sialic acid-containing sugar is an oligosaccharide. More preferably, the oligosaccharide consists of 3-12, preferably 3-11, more preferably 3-10, more preferably 3-9, more preferably 3-8, more preferably 3-7, more preferably 3-6, and most preferably 3-5 monosaccharides. For clarity, in this application and claims, the expression "xy" refers to the range from x (inclusive) to y (inclusive). For example, 3-5 monosaccharides means the presence of 3, 4, or 5 monosaccharides.

[0046] In a more preferred embodiment, the sialic acid-containing sugar of the present invention comprises lactose, lacto-N-biose (LNB), or N-acetyllactosamine (LacNAc). Preferably, the sialic acid-containing sugar comprises lactose or LacNAc. Most preferably, the sialic acid-containing sugar comprises lactose. For the purposes of this invention, the term "sialic acid-containing sugar comprising lactose, LNB, or LacNAc" refers to a sialic acid-containing sugar containing lactose, LNB, or LacNAc at the reducing end, the non-reducing end, or a position in between. Optionally, the lactose (or LNB or LacNAc) further comprises one or more additional monosaccharides at the reducing end of the lactose (or LNB or LacNAc) and / or further comprises one or more additional monosaccharides at the non-reducing end of the lactose (or LNB or LacNAc). For example, 6'SL is a sialic acid-containing sugar that contains lactose (at the reducing end of 6'SL).

[0047] In an even more preferred embodiment, the sialic acid-containing sugar according to the present invention comprises lactose, lacto-N-biose (LNB) or N-acetyllactosamine (LacNAc) at its reducing end. Preferably, the sialic acid-containing sugar comprises lactose or LacNAc at its reducing end. Most preferably, the sialic acid-containing sugar comprises lactose at its reducing end.

[0048] The sugar containing lactose at its reducing end, and wherein the sialic acid is a nonacarboxylic acid, is preferably selected from 3'-sialyl-lactose (3'SL), 6'-sialyl-lactose (6'SL), 3,6-disialyl-lactose, 6,6'-disialyl-lactose, 8,3-disialyl-lactose, 3'S-2'FL, 6'S-2'FL, 3'S-3-FL, 6'S-3-FL, Neu5Ac-α-2,6-(GlcNAc-β-1,3-)Gal-β-1,4-Glc, Neu5Ac-α-2,6-(Neu5Ac-α-2,3-)Gal-β-1,4-Glc, LST a, LST b, LST c, LST d. A list consisting of bis(s)-lacticol-N-tetrasaccharide (DSLNT), bis(s)-lacticol-N-tetrasaccharide analogs (DS'LNT), bis(s)-lacticol-N-neotetrasaccharide (DSLNnT), and bis(s)-lacticol-N-neotetrasaccharide analogs (DS'LNnT); more preferably selected from the list consisting of 3'SL, 6'SL, 3,6-bis(s)-lacticolose, 3'S-2'FL, 6'S-2'FL, 3'S-3-FL, 6'S-3-FL, Neu5Ac-α-2,6-(GlcNAc-β-1,3-)Gal-β-1,4-Glc, Neu5Ac-α-2,6-(Neu5Ac-α-2,3-)Gal-β-1,4-Glc, LST a, LST b, LST c, LST d. A list consisting of DSLNT, DS'LNT, DSLNnT, and DS'LNnT; more preferably selected from 3'SL, 6'SL, 3'S-2'FL, 6'S-2'FL, 3'S-3-FL, 6'S-3-FL, Neu5Ac-α-2,6-(GlcNAc-β-1,3-)Gal-β-1,4-Glc, Neu5Ac-α-2,6-(Neu5Ac-α-2,3-)Gal-β-1,4-Glc, LST a, LST b, LSTc, LST d. A list consisting of DSLNT, DS'LNT, DSLNnT, and DS'LNnT; more preferably selected from 6'SL, 6'S-2'FL, 6'S-3-FL, Neu5Ac-α-2,6-(GlcNAc-β-1,3-)Gal-β-1,4-Glc, LST b, LST c, DSLNT, DSLNnT, DS'LNT and DS'LNnT; more preferably, a list consisting of 6'SL, Neu5Ac-α-2,6-(GlcNAc-β-1,3-)Gal-β-1,4-Glc, LSTb, LST c, DSLNT, DSLNnT, DS'LNT and DS'LNnT;More preferably, the list consisting of 6'SL, LST b, LSTc, Neu5Ac-α-2,6-(GlcNAc-β-1,3-)Gal-β-1,4-Glc, DS'LNT, and DSLNnT is selected; more preferably, 6'SL, LST c, Neu5Ac-α-2,6-(GlcNAc-β-1,3-)Gal-β-1,4-Glc, DS'LNT, or DSLNnT is selected; more preferably, 6'SL, LST c, DS'LNT, or DSLNnT is selected; more preferably, 6'SL or LST c is selected, and most preferably, 6'SL is selected. Alternatively, the sialic acid-containing sugars, which contain lactose at their reducing end and wherein the sialic acid is a nonacarboxylic acid, are preferably selected from the list consisting of 3'SL, 6'SL, LSTa, LSTb, LSTc, LSTd, DSLNT, DSLNnT, DS'LNT, and DS'LNnT; more preferably from the list consisting of 3'SL, 6'SL, LSTa, LSTb, LSTc, and LSTd; even more preferably from the list consisting of 3'SL, 6'SL, LSTb, and LSTc; and most preferably 6'SL, LSTb, or LSTc. Optionally, the sialic acid-containing sugar further comprises fucose, preferably fucose is linked to a monosaccharide via an α-1,2-, α-1,3- or α-1,4- bond, more preferably via an α-1,2- or α-1,3- bond, and more preferably via an α-1,3- bond, and wherein the monosaccharide is preferably selected from glucose, N-acetylglucosamine and galactose.

[0049] The sialic acid-containing sugar, which contains lactose at its reducing end and wherein the sialic acid is octacarbon sialic acid, is preferably 3'KDO-lactose or 6'KDO-lactose.

[0050] The sialic acid-containing sugars, which contain lacto-N-biose (LNB) at their reducing end and wherein the sialic acid is nonacarboxylic acid, are preferably selected from the list consisting of 3'-sialyl lacto-N-biose (3'SLNB), 6'-sialyl lacto-N-biose (6'SLNB), and sialic acid Lewis a; more preferably, the sialic acid-containing sugar is 6'SLNB.

[0051] The sugar containing lacto-N-biose (LNB) at its reducing end, wherein the sialic acid is octose sialic acid, is preferably 3'-KDO-lacto-N-biose (3'KDO-LNB) or 6'-KDO-lacto-N-biose (6'KDO-LNB); more preferably, the sialic acid-containing sugar is 6'KDO-LNB.

[0052] The sialic acid-containing sugars, which contain N-acetyllactosamine (LacNAc) at their reducing end and wherein the sialic acid is a nonacarboxylic acid, are preferably selected from the list consisting of 3'-sialyllactosamine (3'SLacNAc = 3'SLN), 6'-sialyllactosamine (6'SLacNAc = 6'SLN), and sialic acid Lewis x; more preferably, the sialylated sugar is 6'SLacNAc.

[0053] The sugar containing N-acetyllactosamine (LacNAc) at its reducing end, wherein the sialic acid is octose sialic acid, is preferably 3'-KDO-lactosamine (3'KDO-LacNAc) or 6'-KDO-lactosamine (6'KDO-LacNAc); more preferably, the sialic acid-containing sugar is 6'KDO-LacNAc.

[0054] Note that KDO variants of Neu5Ac-containing sugars (e.g., 6'SL) can be produced as follows: by providing CMP-KDO instead of CMP-Neu5Ac, and using a sialylate transferase capable of transferring KDO, preferably a sialylate transferase with a higher affinity for KDO than Neu5Ac, more preferably a sialylate transferase capable only of transferring KDO and not Neu5Ac, in a manner similar to that of the Neu5Ac-containing sugars (e.g., enzymatic or recombinant methods).

[0055] In additional and / or alternative preferred embodiments, the sialic acid-containing sugars of the present invention comprise oligosaccharides selected from the list consisting of 3'SL, 6'SL, 3'SLNB, 6'SLNB, 3'SLacNAc, 6'SLacNAc, 3'KDO-lactose, 6'KDO-lactose, 3'KDO-LNB, 6'KDO-LNB, 3'KDO-LacNAc, and 6'KDO-LacNAc; preferably selected from 6'SL, 6'SLNB, 6'SLAcNAc, 6'KDO-lactose, 6'KDO-LNB, and 6'KDO-LacNAc. A list of cNAcs is preferred; more preferably, a list of 6'SL, 6'SLNB, and 6'SLAcNAcs is selected. Optionally, the oligosaccharide further comprises one or more additional monosaccharides, preferably selected from glucose, galactose, N-acetylglucosamine, N-acetylglucosamine, fucose, and sialic acid, more preferably from a list of glucose, galactose, N-acetylglucosamine, fucose, and sialic acid, even more preferably from a list of galactose, N-acetylglucosamine, fucose, and sialic acid, and most preferably from a list of galactose, N-acetylglucosamine, and fucose. For the purposes of this invention, the term "sialic acid-containing sugar comprising oligosaccharides" refers to a sialic acid-containing sugar in which the oligosaccharide is contained at the reducing end, the non-reducing end, or a position in between of the sialic acid-containing sugar; optionally, the oligosaccharide further comprises one or more additional monosaccharides. In other words, the sialic acid-containing sugar is the same as the oligosaccharide, or has one or more additional monosaccharides at the reducing end of the oligosaccharide and / or one or more additional monosaccharides at the non-reducing end of the oligosaccharide. For example, LSTc is a sialic acid-containing sugar that contains the oligosaccharide 6'SLacNAc, which has two additional monosaccharides, namely galactose-β-1,4-glucose, at the reducing end.

[0056] In a more preferred embodiment, the sialic acid-containing sugar of the present invention comprises oligosaccharides selected from the list consisting of 3'SL, 6'SL, 3'SLNB, 6'SLNB, 3'SLacNAc, 6'SLacNAc, 3'KDO-lactose, 6'KDO-lactose, 3'KDO-LNB, 6'KDO-LNB, 3'KDO-LacNAc, and 6'KDO-LacNAc, preferably selected from 6'SL, 6'SLNB, 6'SLacNAc, 6'KDO-lactose, and 6'KDO-LN. A list consisting of B and 6'KDO-LacNAc; optionally, wherein the oligosaccharide further comprises one or more additional monosaccharides, the monosaccharides preferably being selected from a list consisting of free glucose, galactose, N-acetylglucosamine, N-acetylglucosamine, fucose and sialic acid, more preferably a list consisting of free glucose, galactose, N-acetylglucosamine, fucose and sialic acid, even more preferably a list consisting of free galactose, N-acetylglucosamine, fucose and sialic acid, and most preferably a list consisting of free galactose, N-acetylglucosamine and fucose. Preferably, the sialic acid-containing sugar comprises sialic acid (preferably as described herein, more preferably octose sialic acid, and even more preferably KDO), which is linked to a monosaccharide via α-2,3-, α-2,6-, or α-2,8- bonds, preferably via α-2,3- or α-2,6- bonds, more preferably via α-2,6- bonds, and wherein the monosaccharide is preferably selected from galactose, N-acetylglucosamine, and sialic acid (preferably Neu5Ac), more preferably, the monosaccharide is galactose or N-acetylglucosamine, and even more preferably, the monosaccharide is galactose. The sialic acid-containing sugar of the present invention also preferably comprises lactose, lact-N-biose (LNB), or N-acetylglucosamine (LacNAc), preferably, the sialic acid-containing sugar comprises lactose or LacNAc, and most preferably, the sialic acid-containing sugar comprises lactose. More preferably, the sialic acid-containing sugars of the present invention contain lactose, lacto-N-biose (LNB) or N-acetyllactosamine (LacNAc) at their reducing end. Preferably, the sialic acid-containing sugars contain lactose or LacNAc at their reducing end. Most preferably, the sialic acid-containing sugars contain lactose at their reducing end.

[0057] In a more preferred embodiment, the sialic acid-containing sugar of the present invention comprises oligosaccharides selected from the list consisting of 3'SL, 6'SL, 3'SLNB, 6'SLNB, 3'SLacNAc, and 6'SLacNAc, preferably selected from the list consisting of 6'SL, 6'SLNB, and 6'SLacNAc; optionally, the oligosaccharides further comprise one or more additional monosaccharides, preferably selected from the list consisting of glucose, galactose, N-acetylglucosamine, N-acetylglucosamine, fucose, and sialic acid, more preferably selected from the list consisting of glucose, galactose, N-acetylglucosamine, fucose, and sialic acid, even more preferably selected from the list consisting of galactose, N-acetylglucosamine, fucose, and sialic acid, and most preferably selected from the list consisting of galactose, N-acetylglucosamine, and fucose. Preferably, the sialic acid-containing sugar comprises sialic acid (preferably as described herein, more preferably 9-carbon sialic acid, more preferably Neu5Ac), which is linked to a monosaccharide via α-2,3-, α-2,6-, or α-2,8- bonds, preferably via α-2,3- or α-2,6- bonds, more preferably via α-2,6- bonds, and wherein the monosaccharide is preferably selected from galactose, N-acetylglucosamine, and sialic acid (preferably Neu5Ac), more preferably, the monosaccharide is galactose or N-acetylglucosamine, more preferably, the monosaccharide is galactose. The sialic acid-containing sugar of the present invention also preferably comprises lactose, lact-N-biose (LNB), or N-acetylglucosamine (LacNAc), preferably, the sialic acid-containing sugar comprises lactose or LacNAc, and most preferably, the sialic acid-containing sugar comprises lactose. More preferably, the sialic acid-containing sugars of the present invention contain lactose, lacto-N-biose (LNB) or N-acetyllactosamine (LacNAc) at their reducing end. Preferably, the sialic acid-containing sugars contain lactose or LacNAc at their reducing end. Most preferably, the sialic acid-containing sugars contain lactose at their reducing end.

[0058] In a more preferred embodiment, the sialic acid-containing sugars of the present invention are selected from 3'-sialyl lactose (3'SL), 6'-sialyl lactose (6'SL), 3,6-disialyl lactose, 6,6'-disialyl lactose, 8,3-disialyl lactose, 3'S-2'FL, 6'S-2'FL, 3'S-3-FL, 6'S-3-FL, Neu5Ac-α-2,6-(GlcNAc-β-1,3-)Gal-β-1,4-Glc, Neu5Ac-α-2,6-(Neu5Ac-α-2,3-)Gal-β-1,4-Glc, LST a, LST b, LST c, LST d. Disialyllact-N-tetrasaccharide (DSLNT), disialyllact-N-tetrasaccharide analog (DS'LNT), disialyllact-N-neotetrasaccharide (DSLNnT), disialyllact-N-neotetrasaccharide analog (DS'LNnT), 3'-sialyllact-N-biose (3'SLNB), 6'-sialyllact-N-biose (6'SLNB), sialic acid Lewis a, 3'-sialyllactosamine (3'SLacNAc), 6'-sialyllactosamine (6'SLacNAc), sialic acid Lewis x, 3'KDO-lactose, 6'KDO-lactose, 3'KDO-LNB The list consists of 6'KDO-LNB, 3'KDO-LacNAc, and 6'KDO-LacNAc; more preferably, it consists of 3'-sialyllactose (3'SL), 6'-sialyllactose (6'SL), 3,6-disialyllactose, 3'S-2'FL, 6'S-2'FL, 3'S-3-FL, 6'S-3-FL, Neu5Ac-α-2,6-(GlcNAc-β-1,3-)Gal-β-1,4-Glc, Neu5Ac-α-2,6-(Neu5Ac-α-2,3-)Gal-β-1,4-Glc, and LST. a. LST b. LST c. LST d. A list consisting of bis(s)-lacticol-N-tetrasaccharide (DSLNT), bis(s)-lacticol-N-tetrasaccharide analog (DS'LNT), bis(s)-lacticol-N-neotetrasaccharide (DSLNnT), bis(s)-lacticol-N-neotetrasaccharide analog (DS'LNnT), 3'-sialidol-N-biose (3'SLNB), 6'-sialidol-N-biose (6'SLNB), sialic acid Lewis a, 3'-sialidol-lactosamine (3'SLacNAc), 6'-sialidol-lactosamine (6'SLacNAc), 3'KDO-lactose, 6'KDO-lactose, 3'KDO-LNB, 6'KDO-LNB, 3'KDO-LacNAc and 6'KDO-LacNAc;More preferably, it is selected from 3'-sialyl lactose (3'SL), 6'-sialyl lactose (6'SL), 3'S-2'FL, 6'S-2'FL, 3'S-3-FL, 6'S-3-FL, Neu5Ac-α-2,6-(GlcNAc-β-1,3-)Gal-β-1,4-Glc, Neu5Ac-α-2,6-(Neu5Ac-α-2,3-)Gal-β-1,4-Glc, LST a, LST b, LST c, LST d. Disialyllact-N-tetrasaccharide (DSLNT), disialyllact-N-tetrasaccharide analog (DS'LNT), disialyllact-N-neotetrasaccharide (DSLNnT), disialyllact-N-neotetrasaccharide analog (DS'LNnT), 3'-sialyllact-N-biose (3'SLNB), 6'-sialyllact-N-biose (6'SLNB), sialic acid Lewis a, 3'-sialyllactosamine (3'SLacNAc), 6'-sialyllactosamine (6 The list consisting of 'SLacNAc', sialic acid Lewis x, 3'KDO-lactose, 6'KDO-lactose, 3'KDO-LNB, 6'KDO-LNB, 3'KDO-LacNAc and 6'KDO-LacNAc; more preferably selected from the list consisting of 3'-sialic acid lactose (3'SL), 6'-sialic acid lactose (6'SL), Neu5Ac-α-2,6-(GlcNAc-β-1,3-)Gal-β-1,4-Glc, LST a, LST b, LSTc, LST d, a list consisting of bis(s)-lacticol-N-tetrasaccharide (DSLNT), bis(s)-lacticol-N-tetrasaccharide analog (DS'LNT), bis(s)-lacticol-N-neotetrasaccharide (DSLNnT), bis(s)-lacticol-N-neotetrasaccharide analog (DS'LNnT), 3'-sialidol-N-biose (3'SLNB), 6'-sialidol-N-biose (6'SLNB), sialic acid Lewis a, 3'-sialidol-lactosamine (3'SLacNAc), 6'-sialidol-lactosamine (6'SLacNAc), sialic acid Lewis x, 3'KDO-lactose, 6'KDO-lactose, 3'KDO-LNB, 6'KDO-LNB, 3'KDO-LacNAc and 6'KDO-LacNAc;More preferably, LST a, LSTb, LST c, and LST are selected from 3'-sialyl lactose (3'SL), 6'-sialyl lactose (6'SL), Neu5Ac-α-2,6-(GlcNAc-β-1,3-)Gal-β-1,4-Glc, LST a, LSTb, LST c, and LST c. d. A list consisting of diasialact-N-tetrasaccharide analogs (DS'LNT), diasialact-N-neotetrasaccharides (DSLNnT), 3'-sialact-N-disaccharides (3'SLNB), 6'-sialact-N-disaccharides (6'SLNB), sialic acid Lewis a, 3'-sialic acid lactosamine (3'SLacNAc), 6'-sialic acid lactosamine (6'SLacNAc), sialic acid Lewis x, 3'KDO-lactose, 6'KDO-lactose, 3'KDO-LNB, 6'KDO-LNB, 3'KDO-LacNAc, and 6'KDO-LacNAc; more preferably selected from the list consisting of 3'-sialic acid lactose (3'SL), 6'-sialic acid lactose (6'SL), LST b, LST c, a list consisting of 3'-sialyl-lact-N-biose (3'SLNB), 6'-sialyl-lact-N-biose (6'SLNB), 3'-sialyl-lactosamine (3'SLacNAc), 6'-sialyl-lactosamine (6'SLacNAc), 3'KDO-lactose, 6'KDO-lactose, 3'KDO-LNB, 6'KDO-LNB, 3'KDO-LacNAc and 6'KDO-LacNAc; more preferably, a list consisting of 6'-sialyl-lactose (6'SL), LST b, LST c, 6'-sialyl-lact-N-biose (6'SLNB), 6'-sialyl-lactosamine (6'SLacNAc), 6'KDO-lactose, 6'KDO-LNB and 6'KDO-LacNAc; Optionally, the sialic acid-containing sugar further comprises fucose, preferably fucose is linked to a monosaccharide via an α-1,2-, α-1,3- or α-1,4- bond, more preferably via an α-1,2- or α-1,3- bond, and more preferably via an α-1,3- bond, and wherein the monosaccharide is preferably selected from glucose, N-acetylglucosamine and galactose.

[0059] In a more preferred embodiment, the sialic acid-containing sugars of the present invention are selected from 3'-sialyl lactose (3'SL), 6'-sialyl lactose (6'SL), 3,6-disialyl lactose, 6,6'-disialyl lactose, 8,3-disialyl lactose, 3'S-2'FL, 6'S-2'FL, 3'S-3-FL, 6'S-3-FL, Neu5Ac-α-2,6-(GlcNAc-β-1,3-)Gal-β-1,4-Glc, Neu5Ac-α-2,6-(Neu5Ac-α-2,3-)Gal-β-1,4-Glc, LST a, LST b, LST c, LST d. Disialialoglact-N-tetrasaccharide (DSLNT), disialialoglact-N-tetrasaccharide analog (DS'LNT), disialialoglact-N-neotetrasaccharide (DSLNnT), disialialoglact-N-neotetrasaccharide analog (DS'LNnT), 3'-sialialoglact-N-biose (3'SLNB), 6'-sialialoglact-N-biose (6'SLNB), sialic acid Lewis a, 3'-sialialoglactosamine (3'SLacNAc), 6'-sialialoglactosamine (6'SLacNAc) and sialic acid The list of Lewis x components; more preferably, 3'-sialyl lactose (3'SL), 6'-sialyl lactose (6'SL), 3,6-disialyl lactose, 3'S-2'FL, 6'S-2'FL, 3'S-3-FL, 6'S-3-FL, Neu5Ac-α-2,6-(GlcNAc-β-1,3-)Gal-β-1,4-Glc, Neu5Ac-α-2,6-(Neu5Ac-α-2,3-)Gal-β-1,4-Glc, LST a, LST b, LST c, LST d, a list consisting of bis(s)-lacticol-N-tetrasaccharide (DSLNT), bis(s)-lacticol-N-tetrasaccharide analog (DS'LNT), bis(s)-lacticol-N-neotetrasaccharide (DSLNnT), bis(s)-lacticol-N-neotetrasaccharide analog (DS'LNnT), 3'-sialidol-N-biose (3'SLNB), 6'-sialidol-N-biose (6'SLNB), sialic acid Lewis a, 3'-sialidol-lactosamine (3'SLacNAc), 6'-sialidol-lactosamine (6'SLacNAc) and sialic acid Lewis x;More preferably, it is selected from 3'-sialyl lactose (3'SL), 6'-sialyl lactose (6'SL), 3'S-2'FL, 6'S-2'FL, 3'S-3-FL, 6'S-3-FL, Neu5Ac-α-2,6-(GlcNAc-β-1,3-)Gal-β-1,4-Glc, LST a, LST b, LST c, LST d. A list consisting of bis(sialo-lact-N-tetrasaccharide) (DSLNT), bis(sialo-lact-N-tetrasaccharide) analog (DS'LNT), bis(sialo-lact-N-neo-tetrasaccharide) (DSLNnT), bis(sialo-lact-N-neo-tetrasaccharide) analog (DS'LNnT), 3'-sialo-lact-N-biose (3'SLNB), 6'-sialo-lact-N-biose (6'SLNB), sialic acid Lewis a, 3'-sialo-lactosamine (3'SLacNAc), 6'-sialo-lactosamine (6'SLacNAc), and sialic acid Lewis x; more preferably selected from the list consisting of 3'-sialo-lactose (3'SL), 6'-sialo-lactose (6'SL), Neu5Ac-α-2,6-(GlcNAc-β-1,3-)Gal-β-1,4-Glc, LST a, LST b, LST c, LST d. A list consisting of bis(sialyllact-N-tetrasaccharide) (DSLNT), bis(sialyllact-N-tetrasaccharide) analog (DS'LNT), bis(sialyllact-N-neotetrasaccharide) (DSLNnT), bis(sialyllact-N-neotetrasaccharide) analog (DS'LNnT), 3'-sialyllact-N-biose (3'SLNB), 6'-sialyllact-N-biose (6'SLNB), sialic acid Lewis a, 3'-sialyllactosamine (3'SLacNAc), 6'-sialyllactosamine (6'SLacNAc), and sialic acid Lewis x; more preferably selected from the list consisting of 3'-sialyllactose (3'SL), 6'-sialyllactose (6'SL), Neu5Ac-α-2,6-(GlcNAc-β-1,3-)Gal-β-1,4-Glc, LST a, LST b, LST c, LST d. A list of analogues of diasialact-N-tetrasaccharides (DS'LNT), diasialact-N-neotetrasaccharides (DSLNnT), 3'-sialact-N-bioses (3'SLNB), 6'-sialact-N-bioses (6'SLNB), sialic acid Lewis a, 3'-sialic acid lactosamine (3'SLacNAc), 6'-sialic acid lactosamine (6'SLacNAc) and sialic acid Lewis acids x;More preferably, the list consisting of 3'-sialyl lactose (6'SL), 6'-sialyl lactose (6'SL), LST b, LST c, 3'-sialyl lacto-N-biose (3'SLNB), 6'-sialyl lacto-N-biose (6'SLNB), 3'-sialyl lactosamine (3'SLacNAc), and 6'-sialyl lactosamine (6'SLacNAc) is selected; even more preferably, the list consisting of 6'-sialyl lactose (6'SL), LST b, LST c, 6'-sialyl lacto-N-biose (6'SLNB), and 6'-sialyl lactosamine (6'SLacNAc) is selected; most preferably, 6'SL, LST b, or LSTc is selected. Optionally, the sialic acid-containing sugar further comprises fucose, preferably fucose is linked to a monosaccharide via an α-1,2-, α-1,3- or α-1,4- bond, more preferably via an α-1,2- or α-1,3- bond, and more preferably via an α-1,3- bond, and wherein the monosaccharide is preferably selected from glucose, N-acetylglucosamine and galactose.

[0060] For the purposes of this invention, the sialic acid-containing sugars of this invention are particularly advantageous in the methods of this invention, especially in methods for promoting plant growth and / or development (see the section on "Promoting Growth and / or Development") and in methods for protecting plants against abiotic and / or biotic stresses (see the section on "Abiotic and / or Biological Stresses"). Preferably, the sialic acid is 9-carbon sialic acid or 8-carbon sialic acid, more preferably, the sialic acid is 9-carbon sialic acid, even more preferably, the sialic acid is Neu5Ac), wherein the sialic acid is linked to a monosaccharide via an α-2,6-bond; preferably, the monosaccharide is selected from galactose, N-acetylglucosamine, and sialic acid (preferably Neu5Ac), more preferably, the monosaccharide is galactose or N-acetylglucosamine, even more preferably, the monosaccharide is galactose. Furthermore, the inventors have discovered that sialic acid-containing sugars can significantly improve flower development and flower protection even under abiotic stresses such as frost (see the section on “Abiotic and / or Biological Stresses”). Preferably, the sialic acid is 9-carbon sialic acid or 8-carbon sialic acid, more preferably, the sialic acid is 9-carbon sialic acid, and even more preferably, the sialic acid is Neu5Ac. The sialic acid is linked to the monosaccharide via an α-2,6-bond. Preferably, the monosaccharide is selected from galactose, N-acetylglucosamine, and sialic acid (preferably Neu5Ac). More preferably, the monosaccharide is galactose or N-acetylglucosamine, and even more preferably, the monosaccharide is galactose. In this application and claims, unless otherwise expressly specified, for the purposes of this invention, sialic acid (i.e., sialic acid-containing sugars) linked to monosaccharides via α-2,6-bonds is preferred over sialic acid linked to monosaccharides via α-2,3-bonds or α-2,8-bonds; preferably, the monosaccharide is selected from galactose, N-acetylglucosamine and sialic acid (preferably Neu5Ac), more preferably, the monosaccharide is galactose or N-acetylglucosamine, and even more preferably, the monosaccharide is galactose.

[0061] With respect to the present invention, sialic acid-containing sugars according to the present invention are particularly advantageous in the methods according to the present invention, especially in methods for protecting plants against abiotic and / or biotic stresses (see the section on “Abiotic and / or Biological Stresses”), preferably wherein the sialic acid is 9-carbon sialic acid or 8-carbon sialic acid, more preferably wherein the sialic acid is 9-carbon sialic acid, more preferably wherein the sialic acid is Neu5Ac), wherein the sialic acid is linked to a monosaccharide via an α-2,3-bond; preferably, the monosaccharide is selected from galactose, N-acetylglucosamine and sialic acid (preferably Neu5Ac), more preferably, the monosaccharide is galactose or N-acetylglucosamine, more preferably, wherein the monosaccharide is galactose.

[0062] In another preferred embodiment, the sialic acid-containing sugars of the present invention are isolated from microbial culture or fermentation, cell culture, enzymatic reaction, or chemical reaction. Alternatively, the sialic acid-containing sugars of the present invention are isolated from natural sources (e.g., human milk or animal milk, preferably animal milk) by, for example, chromatography or filtration techniques.

[0063] In additional and / or alternative preferred embodiments, the sialic acid-containing sugars of the present invention are produced by cells (preferably single cells) preferably under in vitro and / or in vitro conditions, wherein the cells are preferably selected from a list consisting of free microorganisms, plant cells, animal cells, and protozoan cells. In other words, the sialic acid-containing sugars of the present invention are produced by in vitro and / or in vitro cultures of cells, wherein the cells are preferably selected from a list consisting of free microorganisms, plant cells, animal cells, or protozoan cells. Preferably, the cells are microorganisms. Preferably, the microorganisms are selected from a list consisting of bacteria, yeast, and fungi. More preferably, the microorganisms are bacteria, and more preferably, the microorganisms are *Escherichia coli* (E. coli). Escherichia coli Furthermore, preferably, the cells are genetically engineered to produce the sialic acid-containing sugars described in this invention.

[0064] The aforementioned sialic acid-containing sugars are commercially available, and / or methods for their production / purification have been described; therefore, those skilled in the art can accordingly produce / obtain any of the aforementioned sialic acid-containing sugars. For example (all references are incorporated herein by reference): -3'SL: Zhang et al., 2022, ACS Synth. Biol. 11(8): p. 2837-2845; Carbosynth (OS04397) -6'SL: Guo et al., 2018, Appl. Environ. Microbiol. 84(13):e00071-18; Carbosynth (OS04398) -3,6-Disialyllactose: Pan et al., 2006, Carbohydr. Res. 341(6): p. 730-737 -6,6'-disialyllactose: Drouillard et al., 2010, Carbohydr. Res. 345(10): p. 1394-1399 -8,3-Disialyllactose: Carbosynth (OD45739) -3'S-3-FL: Biosynth / Cymit Quimica (3D-OSO1065) -LST a: Carbosynth (OL03882) -LST b: Carbosynth (OL03877) -LST c: WO2016 / 199071; Carbosynth (OL06570) -LST d: Carbosynth (OS158776) -3'SLNB: Carbosynth (OS35289) -Sialic acid Lewis a:Carbosynth (OS00745) -Sialic acid Lewis X: Yu et al., 2017, Chem. Commun (Camb) 53 (80): p. 11012-11015; Carbosynth (OS04058) -3'KDO-Lactose: PCT / EP2023 / 058392 -6'KDO-lactose: Drouillard et al., 2010, Carbohydr. Res. 345(10): p. 1394-1399.

[0065] Furthermore, in another preferred embodiment of the invention, the amount of the sialic acid-containing sugar applied to the plant, parts of the plant, seeds of the plant, and / or the intended growth area of ​​the plant is at least 0.10 µg, preferably at least 0.25 µg, more preferably at least 0.50 µg, more preferably at least 1.00 µg, and most preferably at least 1.50 µg. More preferably, the amount of the sialic acid-containing sugar applied is 0.10 µg-100.00 mg, preferably 0.10 µg-75.00 mg, more preferably 0.10 µg-50.00 mg, more preferably 0.10 µg-25.00 mg, more preferably 0.10 µg-10.00 mg, more preferably 0.10 µg-1.00 mg, more preferably 0.10 µg-100.00 µg, more preferably 0.10 µg-75.00 µg, more preferably 0.25 µg-75.00 µg, more preferably 0.50 µg-75.00 µg, more preferably 1.00 µg-75.00 µg, and most preferably 1.00 µg-50.00 µg. When two or more different sialic acid-containing sugars of the present invention are applied, it is preferred that the amount of each sialic acid-containing sugar applied is at least 0.10 µg, more preferably at least 0.25 µg, more preferably at least 0.50 µg, more preferably at least 1.00 µg, and most preferably at least 1.50 µg. More preferably, the amount of each sialic acid-containing sugar is 0.10 µg-100.00 mg, preferably 0.10 µg-75.00 mg, more preferably 0.10 µg-50.00 mg, more preferably 0.10 µg-25.00 mg, more preferably 0.10 µg-10.00 mg, more preferably 0.10 µg-1.00 mg, more preferably 0.10 µg-100.00 µg, more preferably 0.10 µg-75.00 µg, more preferably 0.25 µg-75.00 µg, more preferably 0.50 µg-75.00 µg, more preferably 1.00 µg-75.00 µg, and most preferably 1.00 µg-50.00 µg.

[0066] More preferably, the amount of sialic acid-containing sugars used in this invention is at least 0.10 µmol, preferably at least 0.25 µmol, more preferably at least 0.50 µmol, more preferably at least 1.00 µmol, and most preferably at least 1.50 µmol. More preferably, the application amount is 0.10 µmol-100.00 mmol, more preferably 0.10 µmol-75.00 mmol, more preferably 0.10 µmol-50.00 mmol, more preferably 0.10 µmol-25.00 mmol, more preferably 0.10 µmol-10.00 mmol, more preferably 0.10 µmol-1.00 mmol, more preferably 0.10 µmol-100.00 µmol, more preferably 0.10 µmol-75.00 µmol, more preferably 0.25 µmol-75.00 µmol, more preferably 0.50 µmol-75.00 µmol, more preferably 1.00 µmol-75.00 µmol, and most preferably 1.00 µmol-50.00 µmol. When two or more different sialic acid-containing sugars of the present invention are applied, it is preferred that the amount of each sialic acid-containing sugar applied is at least 0.10 µmol, more preferably at least 0.25 µmol, more preferably at least 0.50 µmol, more preferably at least 1.00 µmol, and most preferably at least 1.50 µmol. More preferably, the amount of each sialic acid-containing sugar applied is 0.10 µmol-100.00 mmol, preferably 0.10 µmol-75.00 mmol, more preferably 0.10 µmol-50.00 mmol, more preferably 0.10 µmol-25.00 mmol, more preferably 0.10 µmol-10.00 mmol, more preferably 0.10 µmol-1.00 mmol, more preferably 0.10 µmol-100.00 µmol, more preferably 0.10 µmol-75.00 µmol, more preferably 0.25 µmol-75.00 µmol, more preferably 0.50 µmol-75.00 µmol, more preferably 1.00 µmol-75.00 µmol, and most preferably 1.00 µmol-50.00 µmol.

[0067] When the sialic acid-containing sugars of the present invention are applied to seeds, it is particularly preferred that the application rate is at least 1.00 mg per ton of seeds, preferably at least 5.00 mg, more preferably at least 10.00 mg, more preferably at least 25.00 mg, more preferably at least 50.00 mg, more preferably at least 75.00 mg, and most preferably at least 100.00 mg. More preferably, the application rate is 0.001 g-100.0 g per ton of seeds, preferably 0.010 g-100.0 g, more preferably 0.025 g-100.0 g, more preferably 0.050 g-100.0 g, more preferably 0.050 g-75.0 g, more preferably 0.075 g-75.0 g, more preferably 0.100 g-75.0 g, and most preferably 0.100 g-60.0 g. One "ton" is 1000 kg. When applying two or more different sialic acid-containing sugars of the present invention, the preferred application amount of each sialic acid-containing sugar is at least 1.00 mg per ton of seeds, preferably at least 5.00 mg, more preferably at least 10.00 mg, more preferably at least 25.00 mg, more preferably at least 50.00 mg, more preferably at least 75.00 mg, and most preferably at least 100.00 mg. More preferably, the amount of each sialic acid-containing sugar is 0.001 g to 100.0 g per ton of seeds, preferably 0.010 g to 100.0 g, more preferably 0.025 g to 100.0 g, more preferably 0.050 g to 100.0 g, more preferably 0.050 g to 75.0 g, more preferably 0.075 g to 75.0 g, more preferably 0.100 g to 75.0 g, and most preferably 0.100 g to 60.0 g.

[0068] More preferably, the application amount of the sialic acid-containing sugars of the present invention is at least 1.0 µmol per ton of seeds, preferably at least 5.0 µmol, more preferably at least 10.0 µmol, more preferably at least 25.0 µmol, more preferably at least 50.0 µmol, more preferably at least 75.0 µmol, more preferably at least 100.0 µmol, and most preferably at least 150.0 µmol. More preferably, the application rate per ton of seed is 1.0 µmol-150.0 mmol, more preferably 10.0 µmol-150.0 mmol, more preferably 25.0 µmol-150.0 mmol, more preferably 50.0 µmol-150.0 mmol, more preferably 75.0 µmol-150.0 mmol, more preferably 75.0 µmol-125.0 mmol, more preferably 100.0 µmol-125.0 mmol, more preferably 125 µmol-125.0 mmol, more preferably 150 µmol-125.0 mmol, and most preferably 150 µmol-100.0 mmol. When two or more different sialic acid-containing sugars of the present invention are applied, more preferably, the application amount of each sialic acid-containing sugar is at least 1.0 µmol per ton of seeds, preferably at least 5.0 µmol, more preferably at least 10.0 µmol, more preferably at least 25.0 µmol, more preferably at least 50.0 µmol, more preferably at least 75.0 µmol, more preferably at least 100.0 µmol, and most preferably at least 150.0 µmol. More preferably, the amount of each sialic acid-containing sugar is 1.0 µmol-150.0 mmol per ton of seeds, preferably 10.0 µmol-150.0 mmol, more preferably 25.0 µmol-150.0 mmol, more preferably 50.0 µmol-150.0 mmol, more preferably 75.0 µmol-150.0 mmol, more preferably 75.0 µmol-125.0 mmol, more preferably 100.0 µmol-125.0 mmol, more preferably 125 µmol-125.0 mmol, more preferably 150 µmol-125.0 mmol, and most preferably 150 µmol-100.0 mmol.

[0069] In a more preferred embodiment of the invention, the amount of the sialic acid-containing sugar applied to the plant, parts of the plant, seeds of the plant and / or the intended growth area of ​​the plant is at least 1.0 mg per hectare of the plant, preferably at least 5.0 mg, more preferably at least 10.0 mg, more preferably at least 25.0 mg, more preferably at least 50.0 mg, more preferably at least 75.0 mg, more preferably at least 100.0 mg, and most preferably at least 250.0 mg. More preferably, the amount of sialic acid-containing sugars is 0.001 g-1000.0 g per hectare of the plant, preferably 0.001 g-500.0 g, more preferably 0.001 g-250.0 g, more preferably 0.001 g-100.0 g, more preferably 0.001 g-50.0 g, more preferably 0.001 g-25.0 g, more preferably 0.001 g-10.0 g, more preferably 0.010 g-10.0 g, more preferably 0.025 g-10.0 g, more preferably 0.025 g-7.5 g, more preferably 0.025 g-5.0 g, more preferably 0.050 g-2.5 g, more preferably 0.050 g-1.5 g, more preferably 0.100 g-1.5 g, more preferably 0.100 g-1.25 g, and most preferably 0.250 g-1.25 g. When two or more different sialic acid-containing sugars of the present invention are applied, preferably, the application amount of each sialic acid-containing sugar is at least 1.0 mg per hectare of said plant, more preferably at least 5.0 mg, more preferably at least 10.0 mg, more preferably at least 25.0 mg, more preferably at least 50.0 mg, more preferably at least 75.0 mg, more preferably at least 100.0 mg, and most preferably at least 250.0 mg. More preferably, the amount of each sialic acid-containing sugar is 0.001 g-1000.0 g per hectare of the plant, preferably 0.001 g-500.0 g, more preferably 0.001 g-250.0 g, more preferably 0.001 g-100.0 g, more preferably 0.001 g-50.0 g, more preferably 0.001 g-25.0 g, more preferably 0.001 g-10.0 g, more preferably 0.010 g-10.0 g, more preferably 0.025 g-10.0 g, more preferably 0.025 g-7.5 g, more preferably 0.025 g-5.0 g, more preferably 0.050 g-2.5 g, more preferably 0.050 g-1.5 g, more preferably 0.100 g-1.5 g, more preferably 0.100 g-1.25 g, and most preferably 0.250 g-1.25 g.

[0070] In a more preferred embodiment of the invention, the amount of sialic acid-containing sugars applied to the plant, parts of the plant, seeds of the plant, and / or the intended growth area of ​​the plant is at least 1.0 µmol per hectare of the plant, preferably at least 5.0 µmol, more preferably at least 10.0 µmol, more preferably at least 25.0 µmol, more preferably at least 50.0 µmol, more preferably at least 75.0 µmol, more preferably at least 100.0 µmol, more preferably at least 150.0 µmol, more preferably at least 200.0 µmol, and most preferably at least 250.0 µmol. More preferably, the amount of sialic acid-containing sugars is 0.001 mmol to 1000.0 mmol per hectare of the plant, preferably 0.001 mmol to 500.0 mmol, more preferably 0.001 mmol to 250.0 mmol, more preferably 0.001 mmol to 100.0 mmol, more preferably 0.001 mmol to 50.0 mmol, more preferably 0.001 to 25.0 mmol, more preferably 0.001 mmol to 10.0 mmol, more preferably 0.010 mmol to 10.0 mmol, more preferably 0.025 mmol to 10.0 mmol, more preferably 0.025 mmol to 7.5 mmol, more preferably 0.025 mmol to 5.0 mmol, more preferably 0.050 mmol to 2.5 mmol, more preferably 0.050 mmol to 2.0 mmol, more preferably 0.075 mmol to 2.0 mmol per hectare of the plant. The concentration of sialic acid-containing sugars is preferably 0.100 mmol to 2.0 mmol, and most preferably 0.100 mmol to 1.50 mmol. When two or more different sialic acid-containing sugars of the present invention are applied, preferably, the application amount of each sialic acid-containing sugar is at least 1.0 µmol per hectare of the plant, preferably at least 5.0 µmol, more preferably at least 10.0 µmol, more preferably at least 25.0 µmol, more preferably at least 50.0 µmol, more preferably at least 75.0 µmol, more preferably at least 100.0 µmol, more preferably at least 150.0 µmol, more preferably at least 200.0 µmol, and most preferably at least 250.0 µmol.More preferably, the amount of each sialic acid-containing sugar is 0.001 mmol to 10.0 mmol per hectare of the plant, preferably 0.010 mmol to 10.0 mmol, more preferably 0.025 mmol to 10.0 mmol, more preferably 0.025 mmol to 7.5 mmol, more preferably 0.025 mmol to 5.0 mmol, more preferably 0.050 mmol to 2.5 mmol, more preferably 0.050 mmol to 2.0 mmol, more preferably 0.075 mmol to 2.0 mmol, more preferably 0.100 mmol to 2.0 mmol, and most preferably 0.100 mmol to 1.50 mmol.

[0071] In another preferred embodiment, the sialic acid-containing sugars of the present invention are in the form of agronomically acceptable salts.

[0072] Suitable salts include, but are not limited to, salts of acceptable inorganic acids, such as salts of hydrochloric acid, sulfuric acid, phosphoric acid, nitric acid, carbonic acid, boric acid, aminosulfonic acid, and hydrobromic acid, or salts of agronomically acceptable organic acids, such as salts of acetic acid, propionic acid, butyric acid, tartaric acid, maleic acid, hydroxymaleic acid, fumaric acid, malic acid, citric acid, lactic acid, viscous acid, gluconic acid, benzoic acid, succinic acid, oxalic acid, phenylacetic acid, methanesulfonic acid, toluenesulfonic acid, benzenesulfonic acid, salicylic acid, sulfanilic acid, aspartic acid, glutamic acid, ethylenediaminetetraacetic acid, stearic acid, palmitic acid, oleic acid, lauric acid, pantothenic acid, tannic acid, ascorbic acid, and valeric acid. Suitable salts also include salts of inorganic and organic bases, such as salts of counterions like sodium, calcium, potassium, lithium, magnesium, nickel, zinc, iron, selenium, ammonium, and trimethylsulfonium. These compounds may also be obtained, stored, and / or used in the form of N-oxides. In addition, it includes acid addition salts or base salts in which the counterion is optically active, such as d-lactate or l-lysine salts, or is a racemic mixture, such as dl-tartrate or dl-arginine salt.

[0073] In another preferred embodiment of the invention, the sialic acid-containing carbohydrate of the present invention is linked (preferably chemically linked) to a carrier to deliver the sialic acid-containing carbohydrate. The linking of the carbohydrate to the carrier can improve its affinity. Preferably, the carrier is a ceramide-based carrier or a peptide-based carrier, more preferably, the carrier is a ceramide-based carrier. Preferably, the peptide-based carrier is ε-polylysine, α-polylysine, polyaspartic acid, polyglutamic acid, or polyornithine. These carriers are commercially available (e.g., Sigma-Aldrich, Carbosynth). The ceramide-based carrier is preferably selected from the list consisting of d18:1 / 16:0, t18:0-16:0, t18:0-h16:0, t18:0-h22:0, and t18:0-h24:0. These ceramide carriers are commercially available and well known to those skilled in the art, for example, as described in WO2010 / 037785, which is incorporated herein by reference. d18:1 / 16:0 is also known as C16 ceramide and N-palmitoylsphingosine, and therefore can be used interchangeably herein. t18:0-16:0 is also known as C16 phytoceramide and N-hexadecanoylphytosphingosine, and therefore can be used interchangeably herein. t18:0-h16:0, t18:0-h22:0, and t18:0-h24:0 are glycosylinositol phosphoceramides (GIPC). As will be known to those skilled in the art, “d” and “t” refer to the hydroxylation state of the entire ceramide or the long-chain base moiety (d for 2 groups, t for 3 groups), while “h” indicates the hydroxylation of the fatty acyl group.

[0074] In another preferred embodiment, the sialic acid-containing sugars, and optionally any (preferably all) additional sialic acid-containing sugars, are preferably encapsulated (i.e., forming an encapsulation). This is particularly advantageous for protecting the sugars. If any additional sugars are applied to the plant (see the "Additional Sugars" section), it is preferable to encapsulate any (preferably all) additional sugars. Preferably, all sugars applied to the plant are co-encapsulated.

[0075] Preferably, the encapsulant is a core-shell type, that is, the carrier material forms a shell around the active agent (i.e., the sialylated sugar of the present invention). Preferably, the median diameter (D(v,0.5)) of the core is 125-250 µm, more preferably 150-250 µm, more preferably 165-250 µm, and most preferably 165-225 µm. Furthermore, the median diameter (D(v,0.5)) of the encapsulant is 20-100 µm longer than the median diameter of the core, preferably 20-75 µm, and more preferably 35-75 µm.

[0076] The carrier material preferably comprises a hot-melt material, more preferably an oil and / or wax, even more preferably a hydrogenated oil and / or wax, and optionally further comprises starch. Preferably, the starch comprises less than 15% (w / w) of the carrier material, and more preferably, the starch comprises less than 10% (w / w) of the carrier material.

[0077] The oil is preferably selected from the list consisting of palm oil, sunflower seed oil, soybean oil, rapeseed oil, coconut oil, babassu oil, palm kernel oil, corn oil, sesame oil, and cottonseed oil; more preferably, the oil is selected from the list consisting of palm oil, sunflower seed oil, soybean oil, and rapeseed oil; even more preferably, the oil is palm oil; most preferably, the oil is hydrogenated palm oil.

[0078] The wax is preferably selected from the list consisting of candelilla wax, carnauba wax, beeswax, rice bran wax, paraffin wax, jojoba wax, microcrystalline wax, and Japanese wax; more preferably, the wax is candelilla wax or carnauba wax; most preferably, the wax is candelilla wax.

[0079] More preferably, the content of sialic acid-containing sugars or all sialic acid-containing sugars or all sugars in the encapsulation accounts for 5-50% (w / w) of the total weight of the encapsulation, preferably 10-40% (w / w), more preferably 20-40% (w / w), and even more preferably 20-35% (w / w).

[0080] In another preferred embodiment, the sialic acid-containing sugars of the present invention are milk accharides and / or Lewis antigen sugars. Preferably, the Lewis antigen sugars are sialic acid Lewis a or sialic acid Lewis x.

[0081] In a more preferred embodiment, the sialic acid-containing sugars of the present invention are milk sugars, i.e., sugars that can be found in the milk of animals (preferably mammals and / or humans). For the purposes of the present invention, preferably, the sialylated sugars of the present invention are milk oligosaccharides, i.e., sialic acid-containing oligosaccharides that can be found in the milk of animals (preferably mammals and / or humans).

[0082] Preferably, the sugars / milk oligosaccharides of the milk are mammalian milk sugars / mammalian milk oligosaccharides (MMOs). More preferably, the sugars / milk oligosaccharides of the milk are human milk sugars / human milk oligosaccharides (HMOs).

[0083] As understood by those skilled in the art, mammalian lactooligosaccharides (MMOs) comprise oligosaccharides present in milk at any stage of lactation, including oligosaccharides from human colostrum (i.e., human milk oligosaccharides or HMOs) and oligosaccharides from colostrum of mammals, including but not limited to cattle ( Bos Taurus ),sheep(Ovis aries ),goat( Capra aegagrus hircus Bactrian camel Camelus bactrianus ),horse( Equus ferus caballus ),pig( Sus scropha ),dog( Canis lupus familiaris ) 、 Ezo brown bear ( Ursus arctos yesoensis ), polar bear ( Ursus maritimus ), Japanese black bear ( Ursus thibetanus japonicus ), striped skunk ( Mephitis mephitis ), hooded seal ( Cystophora cristata Asian elephant ( Elephas maximus African elephant Loxodonta africana ), giant anteater ( Myrmecophaga tridactyla ), bottlenose dolphin ( Tursiops truncates Northern minke whale ( Balaenoptera acutorostrata ), Tamar wallaby ( Macropus eugenii ), Red Kangaroo ( Macropus rufus ), brushtail possum ( Trichosurus Vulpecula ),koala( Phascolarctos cinereus ), East Bag Weasel ( Dasyurus viverrinus ),platypus( Ornithorhynchus anatinus(Urashima T. et al., 2011, Milk Oligosaccharides, Nova Biomedical Books, New York ISBN 978-1-61122-831-1; Coppa et al., 2013, Ital. J. Pediatr. 2013, 39(2)). The structures of a large number of milk sugars have now been elucidated. Most lactooligosaccharides found in mammals and animals such as humans contain lactose at the reducing end (Urashima et al., 2011). Other lactooligosaccharides contain N-acetyllactosamine (Gal-β1,4-GlcNAc) or lacto-N-disaccharide (Gal-β1,3-GlcNAc) at the reducing end (Urashima et al., 2011; Wrigglesworth et al., 2020, PLoS ONE 15(12); Urashima et al., 2013, Biosci. Biotechnol. Biochem 77(3): p.455-466; Wei et al., 2018, Sci. Rep. 8:4688). Examples are 3'-SLN (Neu5Ac-α2,3-Gal-β1,4-GlcNAc) and 6'-SLN (Neu5Ac-α2,6-Gal-β1,4-GlcNAc) (Urashima et al., 2011; Wrigglesworth et al., 2020; Wei et al., 2018). Furthermore, the sugars in milk include milk glycosaminoglycans (GAG; Coppa et al., 2013; Rai et al., 2021, Int. J. Biol. Macromolecules, 193(A): p. 137-144). For the purposes of this invention, preferably, the sialic acid-containing sugars described herein are not glycosaminoglycans.

[0084] In this application and claims, "mammalian lactooligosaccharide (MMO)" is preferably "human lactooligosaccharide (HMO)".

[0085] Additional saccharides Optionally, one or more additional sugars are applied in the method of the present invention, preferably one or more additional oligosaccharides, more preferably one or more additional lactooligosaccharides, even more preferably one or more additional mammalian lactooligosaccharides, and most preferably one or more additional human lactooligosaccharides. When the sialic acid-containing sugars and one or more additional sugars of the present invention are applied to the plant, parts of the plant, seeds of the plant, and / or the intended growth area of ​​the plant, preferably, the sialic acid-containing sugars and any (preferably all) additional sugars are applied on the same day, more preferably simultaneously, and more preferably in the form of a composition (preferably, a composition according to the "Composition" section).

[0086] In a preferred embodiment, one or more additional sugars are sialic acid-containing sugars as described herein (see the section “Sialic Acid-Containing Sugars”).

[0087] For the purposes of this invention, an additional and / or alternative preferred embodiment is that one or more additional sugars are sugars that are synthetic intermediates of the sialic acid-containing sugars of this invention (see the section "Sialic Acid-Containing Sugars"). As those skilled in the art will understand, the production of sialic acid-containing sugars requires one or more steps. Each step in the reaction cascade generates an intermediate sugar.

[0088] Compared to the final sialic acid-containing sugar, the intermediate sugars typically lack one or more monosaccharides. For example, possible intermediates in the synthesis of LSTc are lactose, lacto-N-trisaccharide II (LN3, LNT-II), and lacto-N-neotetrasaccharide (LNnT). A possible intermediate in the synthesis of 3'SL is lactose. A possible intermediate in the synthesis of 3'KDO-lactose is lactose.

[0089] The intermediate sugar is preferably a disaccharide or an oligosaccharide.

[0090] According to the sialic acid-containing sugars of the present invention, the intermediate sugars are preferably selected from: -3'SL: Lactose; -6'SL: Lactose; -6,6'-disialyllactose: lactose and 6'SL; -8,3-Disialyllactose: lactose and 3'SL; -3'S-2'FL: lactose and 2'FL; -6'S-2'FL: Lactose and 2'FL -3'S-3-FL: lactose and 3-FL; -6'S-3-FL: lactose and 3-FL; -Neu5Ac-α-2,6-(GlcNAc-β-1,3-)Gal-β-1,4-Glc: lactose, LN3 and 6'SL; -Neu5Ac-α-2,6-(Neu5Ac-α-2,3-)Gal-β-1,4-Glc: lactose, 3'SL and 6'SL; -LST a: lactose, LN3, and LNT; -LST b: lactose, LN3, and LNT; -LST c: lactose, LN3, and LNnT; -LST d: lactose, LN3, and LNnT; -Disialotrol-N-tetrasaccharide (DSLNT): lactose, LN3, LNT, LST a, and LST b; - Disialiacid lact-N-tetrasaccharide analogs (DS'LNT): lactose, 6'SL, LN3, LNT and neu5Ac-α-2,6-Gal-β-1,3-GlcNAc-β-1,3-Gal-β-1,4-Glc; -Disialial lacto-N-neotetrasaccharide (DSLNnT): lactose, LN3, LNnT, 6'SL and LST c; -Disialial lacto-N-neo-tetrasaccharide analogs (DS'LNnT): lactose, LN3, LNnT, 6'SL and LST d; -3'KDO-lactose: lactose; -6'KDO-lactose: lactose; -3'-KDO-lacto-N-disaccharide (3'-KDO-LNB): LNB; -6'-KDO-lacto-N-disaccharide (6'KDO-LNB): LNB; -3'-Sialolact-N-disaccharide (3'SLNB): LNB: -6'-Sialolact-N-disaccharide (6'SLNB): LNB; -Sialic Lewis a: Lactose and 4-fucosylated lact-N-biose (4FLNB); -3'-Sialylactosamine (3'SLacNAc=3'SLN): LacNAc; -6'-Sialylactosamine (6'SLacNAc=6'SLN): LacNAc; - Sialic Lewis x: LacNAc and 3-fucosyl-N-acetyllactosamine (3FlacNAc); -3'-KDO-Lactosamine (3'KDO-LacNAc): LacNAc; -6'-KDO-Lactosamine (6'KDO-LacNAc:LacNAc.

[0091] An additional and / or alternative preferred embodiment for the purposes of this invention is that one or more additional sugars are sialic acid. As described above, sialic acid is a monosaccharide. Preferably, the sialic acid has a nine-carbon skeleton (i.e., nine-carbon sialic acid) or an eight-carbon skeleton (i.e., eight-carbon sialic acid), more preferably a nine-carbon skeleton (i.e., nine-carbon sialic acid). Sialic acid having a nine-carbon skeleton is well known to those skilled in the art and refers to a group of monosaccharides derived from an acidic nine-carbon parent compound—N-acetylneuraminic acid (Neu5Ac) or 2-keto-3-deoxynonanoic acid (Kdn; the deamination form of N-acetylneuraminic acid)—through modification (such as the addition of acetyl, phosphate, methyl, sulfate, and / or lactate groups). Furthermore, the N-acetyl group of Neu5Ac can be hydroxylated to generate N-hydroxyacetylneuraminic acid (Neu5Gc). More than 50 different examples of sialic acid with a nine-carbon skeleton are known (Essentials of Glycobiology, 2nd edition, 2009, Chapter 14, Varki and Schauer). Sialic acid with an eight-carbon skeleton is structurally related to sialic acid with a nine-carbon skeleton, particularly to Kdn (Essentials of Glycobiology, 2nd edition, 2009, Chapter 14, Varki and Schauer). Therefore, the term "sialic acid with an eight-carbon skeleton" is preferably replaced with "eight-carbon 2-keto-3-deoxyoctanoic acid".

[0092] More preferably, the sialic acid is (i) nonacarbon sialic acid, preferably selected from the list of the following: Neu5Ac; Neu4Ac; Neu4,5Ac2; Neu5,7Ac2; Neu5,8Ac2; Neu5,9Ac2; Neu4,5,9Ac3; Neu5,7,9Ac3; Neu5,8,9Ac3; Neu4,5,7,9Ac4; Neu5,7,8,9Ac4; Neu4,5,7,8,9Ac5 and Neu5Gc; more preferably, the nonacarbon sialic acid is N-acetylneuraminic acid (i.e., Neu5Ac). In this application and claims, the term "nine-carbon sialic acid" is preferably replaced by "N-acetylneuraminic acid (Neu5Ac)"; or (ii) octose sialic acid, preferably, wherein the octose sialic acid is ketodeoxyoctanoic acid (KDO; i.e., 2-keto-3-deoxy-D-mannulocylic acid, also known as 2-oxo-3-deoxy-D-mannulocylic acid, 3-deoxy-D-mannuno-2-ketogonic acid, 3-deoxy-D-mannuno-2-octulose or 3-deoxy-D-mannuno-2-ketopyranose). In this application and claims, the term "octose sialic acid" is preferably replaced by "octose 2-keto-3-deoxyoctanoic acid", more preferably by "ketodeoxyoctanoic acid (KDO)".

[0093] More preferably, the sialic acid is N-acetylneuraminic acid (Neu5Ac) or ketodeoxyoctanoic acid (KDO), preferably N-acetylneuraminic acid (Neu5Ac).

[0094] An additional and / or alternative preferred embodiment for the purposes of this invention is that one or more additional sugars are non-fucosylated sugars, preferably non-fucosylated oligosaccharides, more preferably non-fucosylated lactose oligosaccharides, even more preferably non-fucosylated mammalian lactose oligosaccharides, and most preferably non-fucosylated human lactose oligosaccharides. Preferably, the non-fucosylated sugars / oligosaccharides are neutral non-fucosylated sugars / oligosaccharides. "Non-fucosylated" sugars refer to sugars that do not contain fucose. "Neutral" sugars, as used herein and as commonly understood in the art, refer to sugars that do not contain a negative charge derived from a carboxylic acid group.

[0095] In this regard, a preferred embodiment is that the unfucosylated sugar is a disaccharide or an oligosaccharide. In a more preferred embodiment, the unfucosylated sugar is an oligosaccharide. More preferably, the oligosaccharide consists of 3-12, preferably 3-11, more preferably 3-10, more preferably 3-9, more preferably 3-8, more preferably 3-7, more preferably 3-6, and most preferably 3-5 monosaccharides.

[0096] In a more preferred embodiment, the non-fucosylated sugars of the present invention are milk sugars (preferably mammalian milk sugars), preferably lactooligosaccharides, more preferably mammalian lactooligosaccharides, and most preferably human milk oligosaccharides.

[0097] In an additional and / or alternative preferred embodiment, the unfucosylated sugar comprises lactose, lacto-N-biose (LNB), or N-acetyllactosamine (LacNAc). Preferably, the unfucosylated sugar comprises lactose or LacNAc. More preferably, the unfucosylated sugar comprises lactose. More preferably, the unfucosylated sugar comprises lacto-N-trisaccharide II (LNT-II). Most preferably, the unfucosylated sugar comprises lacto-N-tetrasaccharide (LNT) or lacto-N-neotetrasaccharide (LNnT). Optionally, the unfucosylated sugar further comprises one or more additional monosaccharides, preferably selected from the list consisting of glucose, galactose, N-acetylglucosamine, and N-acetylgalactosamine, more preferably selected from the list consisting of glucose, galactose, and N-acetylglucosamine, and more preferably selected from galactose and N-acetylglucosamine. More preferably, the non-fucosylated sugar contains lactose, lacto-N-biose (LNB), or N-acetyllactosamine (LacNAc) at its reducing end. Preferably, the non-fucosylated sugar contains lactose or LacNAc at its reducing end. More preferably, the non-fucosylated sugar contains lactose at its reducing end. More preferably, the non-fucosylated sugar contains lacto-N-trisaccharide II (LNT-II) at its reducing end. Most preferably, the non-fucosylated sugar contains lacto-N-tetrasaccharide (LNT) or lacto-N-neotetrasaccharide (LNnT) at its reducing end.

[0098] Non-fucosylated sugars containing lactose at their reducing end are preferably selected from lactose, lacto-N-trisaccharide II (LN3, LNT-II), lacto-N-neotetrasaccharide (LNnT), lacto-N-tetrasaccharide (LNT), p-lacto-N-neopentasaccharide, p-lacto-N-pentasaccharide, p-lacto-N-neohexasaccharide (pLNnH), p-lacto-N-hexasaccharide (pLNH), β-(1,3)galactosyl-p-lacto-N-neopentasaccharide, β-(1,4)galactosyl -para-lact-N-pentasaccharides, Gal-a1,4-Gal-b1,4-Glc (Gal-a1,4-lactose), β3'-galactosyllactose, β6'-galactosyllactose, Gal-a1,4-Gal-a1,4-Gal-b1,4-Glc, Gal-a1,4-Gal-a1,4-Gal-a1,4-Gal-b1,4-Glc, Gal-b1,3-Gal-b1,3-Gal -b1,4-Glc、Gal-b1,3-Gal-b1,3-Gal-b1,3-Gal-b1,4-Glc、Gal-b1,3-Gal-b1,3-Gal-b1,3-Ga l-b1,3-Gal-b1,4-Glc、Gal-b1,3-Gal-b1,3-Gal-b1,3-Gal-b1,3-Galb1,3-Gal-b1,4-Glc、Gal NAc-b1,3-Gal-b1,4-Glc (GalNAc-b1,3-lactose), Gal-b1,3-GalNAc-b1,3-lactose, GalNAc-b1,3-Gal-a 1,4-Gal-b1,4-Glc (Globo-N-tetrasaccharide), Gal-b1,3-GalNAc-b1,3-Gal-a1,4-Gal-b1,4-Glc, GalNAc-b1,3-LNT, Gal-b1,3-GalNAc-b1,3-LNT, novo-LNT (GlcNAc-b1,6-[Gal-b1,3]-Gal-b1,4-Glc), Gal- novo- LNP I (Gal-b1,4-GlcNAc-b1,6-[Gal-b1,3-Gal-b1,3]-Gal-b1,4-Glc), Gal- novo- LNP II (Gal-b1,4-GlcNAc-b1,6-[Gal-b1,3]-Gal-b1,3-Gal-b1,4-Glc), Gal- novo-LNPIII (Gal-b1,3-Gal-b1,4-GlcNAc-b1,6-[Gal-b1,3]-Gal-b1,4-Glc), novo-LNO, GalNAc-b1,3-LNnT, Gal-b1,3-GalNAc-b1,3-LNnT, lact-N-hexasaccharide (LNH), p-lacto-N-hexasaccharide (pLNH), lact-N-neohexaccharide (LNnH), iso-LNO, novo-LNO, novo-LNnO, LND, iso-LND, GalNAc-a1,3-Gal-b1,4-Glc, novo-LNP I. A list consisting of iso-LNT, DGalLNnH, Galilipentasaccharide, lact-N-heptaose, lact-N-neoheptaose, para-lact-N-neoheptaose, para-lact-N-heptaose, lact-N-octaose (LNO), lact-N-neooctaose, iso-lact-N-octaose, para-lact-N-octaose, iso-lact-N-neooctaose, novo-lact-N-neooctaose, para-lact-N-neooctaose, iso-lact-N-nonaose, novo-lact-N-nonaose, lact-N-nonaose, lact-N-decanose, iso-lact-N-decanose, novo-lact-N-decanose, and lact-N-neodecanoose; more preferably, lactose, lact-N-trisaccharide II (LN3), and lact-N-neotetrasaccharide (LN nT), lact-N-tetrasaccharide (LNT), p-lacto-N-neopentose, p-lacto-N-pentasaccharide, p-lacto-N-neopentose (pLNnH), p-lacto-N-hexasaccharide (pLNH), p-lacto-N-hexasaccharide (pLNH), β-(1,3)galactosyl-p-lacto-N-neopentose, β-(1,4)galactosyl-p-lacto-N-pentasaccharide, Gal-a1,4-Gal-b1,4-Glc (Gal-a1,4-lactose), β3'-galactosyllactose, β6'-galactosyllactose, GalNAc-b1,3-lactose, globulin-N-tetrasaccharide, lact-N-heptasaccharide, lact-N-neopentose, p-lacto-N-neopentose, p-lacto-N-heptasaccharide, lact-N-octasaccharide (LNO), lact-N-neopentose, A list consisting of isoylacto-N-octasaccharide, para-lacto-N-octasaccharide, isoylacto-N-neoctasaccharide, novo-lacto-N-neoctasaccharide, para-lacto-N-neoctasaccharide, isoylacto-N-nonasugar, novo-lacto-N-nonasugar, lact-N-nonasugar, lact-N-decansaccharide, isoylacto-N-decansaccharide, novo-lacto-N-decansaccharide, and lact-N-neocdecansaccharide; more preferably, a list consisting of lactose, lacto-N-trisaccharide II (LN3, LNT-II), lacto-N-neoctetrate (LNnT), lacto-N-tetrasaccharide (LNT), para-lacto-N-neoctetrate, para-lacto-N-pentasaccharide, para-lacto-N-neoctetrate, para-lacto-N-neoctetrate, lacto-N-hexasaccharide, and lacto-N-neoctetrate;More preferably, the list consisting of lactose, lacto-N-trisaccharide II (LN3, LNT-II), lacto-N-neotetrasaccharide (LNnT), lacto-N-tetrasaccharide (LNT), p-lacto-N-neopentasaccharide, p-lacto-N-pentasaccharide, LNnH, LNH, p-lacto-N-neohexasaccharide (pLNnH), and p-lacto-N-hexasaccharide (pLNH) is selected; most preferably, the list consisting of lactose, lacto-N-trisaccharide, lacto-N-tetrasaccharide, and lacto-N-neotetrasaccharide is selected. For the purposes of this invention, the non-fucosylated sugar is preferably not lactose.

[0099] The non-fucosylated sugars containing lacto-N-biose (LNB) at their reducing end are preferably lacto-N-biose (LNB) or diLNB (Gal-β-1,3-GlcNAc-β-1,3-Gal-β-1,3-Glc), more preferably lacto-N-biose (LNB).

[0100] Non-fucosylated sugars containing N-acetyllactosamine (LacNAc) at their reducing end are preferably selected from the list of acetyllactosamine, diLacNAc (Gal-β-1,4-GlcNAc-β-1,3-Gal-β-1,4-GlcNAc), and poly-LacNAc, more preferably N-acetyllactosamine or diLacNAc.

[0101] In an additional and / or alternative preferred embodiment, the non-fucosylated sugar of the present invention comprises a sugar selected from the list consisting of lactose, LNB, LacNAc, LNT-II, LNT, and LNnT; preferably selected from the list consisting of LNT-II, LNT, and LNnT; optionally, the sugar further comprises one or more additional monosaccharides, preferably selected from the list consisting of glucose, galactose, N-acetylglucosamine, and N-acetylglucosamine, more preferably selected from the list consisting of glucose, galactose, and N-acetylglucosamine, and even more preferably selected from galactose and N-acetylglucosamine. For the purposes of this invention, the term "non-fucosylated sugar comprising a sugar" refers to a non-fucosylated sugar containing the sugar at the reducing end, the non-reducing end, or a position between the two of the non-fucosylated sugar; optionally, the sugar further comprises one or more additional monosaccharides to constitute the non-fucosylated sugar. In other words, the non-fucosylated sugar is the same as the sugar, or has one or more additional monosaccharides at the reducing end of the sugar and / or has one or more additional monosaccharides at the non-reducing end of the sugar. For example, LNT I is a non-fucosylated sugar that contains the oligosaccharide LNT-II, which has an additional monosaccharide, galactose, at the non-reducing end.

[0102] In a more preferred embodiment, the non-fucosylated sugar of the present invention comprises a sugar selected from the list consisting of lactose, LNB, LacNAc, LNT-II, LNT, and LNnT; preferably selected from the list consisting of LNT-II, LNT, and LNnT; optionally, the sugar further comprises one or more additional monosaccharides, preferably selected from the list consisting of glucose, galactose, N-acetylglucosamine, and N-acetylglucosamine, more preferably selected from the list consisting of glucose, galactose, and N-acetylglucosamine, and even more preferably selected from galactose and N-acetylglucosamine. Preferably, the non-fucosylated sugar of the present invention comprises lactose, lact-N-biose (LNB), or N-acetylglucosamine (LacNAc) at its reducing end; preferably, the non-fucosylated sugar comprises lactose or LacNAc at its reducing end; more preferably, the non-fucosylated sugar comprises lactose at its reducing end; most preferably, the non-fucosylated sugar comprises LNT-II at its reducing end.

[0103] In a more preferred embodiment, the non-fucosylated sugars of the present invention are selected from lactose, lacto-N-trisaccharide II (LN3, LNT-II), lacto-N-neotetrasaccharide (LNnT), lacto-N-tetrasaccharide (LNT), para-lacto-N-neopentose, para-lacto-N-pentasaccharide, lacto-N-neopentose, para-lacto-N-neopentose, lacto-N-hexasaccharide, para-lacto-N-neopentose, β-(1,3)galactosyl-para-lacto-N-neopentose, β-(1,4)galactosyl-para-lacto-N-pentasaccharide, Gal-al, 4-Gal-b1,4-Glc (Gal-a1,4-lactose), β3'-galactosyllactose, β6'-galactosyllactose, Gal-a1,4-Gal-a1,4-Gal-b1,4-Glc, Gal-a1,4-Gal-a1,4-Gal-a1,4-Gal-b1,4-Glc, Gal-b1,3-Gal-b1,3-Gal-b1,3-Gal-b1,3-Gal-b1,3-Glc al-b1,4-Glc、Gal-b1,3-Gal-b1,3-Gal-b1,3-Gal-b1,3-Gal-b1,4-Glc、Gal-b1,3-Gal-b1,3-Gal-b1,3-Ga l-b1,3-Gal-b1,3-Gal-b1,4-Glc, GalNAc-b1,3-Gal-b1,4-Glc (GalNAc-b1,3-lactose), Gal-b1,3-GalNAc-b1,3 -Lactose, GalNAc-b1,3-Gal-a1,4-Gal-b1,4-Glc (globul-N-tetrasaccharide), Gal-b1,3-GalNAc-b1,3-Gal-a1,4-Gal-b1,4-Glc, G alNAc-b1,3-LNT, Gal-b1,3-GalNAc-b1,3-LNT, novo-LNT (GlcNAc-b1,6-[Gal-b1,3]-Gal-b1,4-Glc), Gal- novo- LNP I (Gal-b1,4-GlcNAc-b1,6-[Gal-b1,3-Gal-b1,3]-Gal-b1,4-Glc), Gal- novo- LNP II (Gal-b1,4-GlcNAc-b1,6-[Gal-b1,3]-Gal-b1,3-Gal-b1,4-Glc), Gal- novo-LNP III (Gal-b1,3-Gal-b1,4-GlcNAc-b1,6-[Gal-b1,3]-Gal-b1,4-Glc), novo-LNO, GalNAc-b1,3-LNnT, Gal-b1,3- GalNAc-b1,3-LNnT, LNH, LNnH, iso-LNO, novo-LNO, novo-LNnO, LND, iso-LND, GalNAc-a1,3-Gal-b1,4-Glc, novo-LNP List of I, iso-LNT, DGalLNnH, Galili pentasaccharide, lact-N-hepta-saccharide, lact-N-neo-hepta-saccharide, para-lact-N-neo-hepta-saccharide, para-lact-N-hepta-saccharide, lact-N-octa-saccharide (LNO), lact-N-neo-octa-saccharide, iso-lact-N-octa-saccharide, para-lact-N-octa-saccharide, iso-lact-N-neo-octa-saccharide, novo-lact-N-neo-octa-saccharide, para-lact-N-neo-octa-saccharide, iso-lact-N-nona-saccharide, novo-lact-N-nona-saccharide, lact-N-nona-saccharide, lact-N-decapsaccharide, iso-lact-N-decapsaccharide, novo-lact-N-decapsaccharide, lact-N-neo-decapsaccharide, LNB, diLNB, LacNAc, diLacNAc and poly-LacNAc.More preferably, the non-fucosylated sugars of the present invention are selected from lacto-N-trisaccharide II (LN3, LNT-II), lacto-N-neotetrasaccharide (LNnT), lacto-N-tetrasaccharide (LNT), p-lacto-N-neopentasaccharide, p-lacto-N-pentasaccharide, lacto-N-neohexasaccharide, p-lacto-N-neohexasaccharide, lacto-N-hexasaccharide, p-lacto-N-hexasaccharide, β-(1,3)galactosyl-p-lacto-N-neopentasaccharide, β-(1,4)galactosyl -para-lact-N-pentasaccharides, Gal-a1,4-Gal-b1,4-Glc (Gal-a1,4-lactose), β3'-galactosyllactose, β6'-galactosyllactose, Gal-a1,4-Gal-a1,4-Gal-b1,4-Glc, Gal-a1,4-Gal-a1,4-Gal-a1,4-Gal-b1,4-Glc, Gal-b1,3-Gal-b1,3 -Gal-b1,4-Glc,Gal-b1,3-Gal-b1,3-Gal-b1,3-Gal-b1,4-Glc,Gal-b1,3-Gal-b1,3-Gal-b 1,3-Gal-b1,3-Gal-b1,4-Glc、Gal-b1,3-Gal-b1,3-Gal-b1,3-Gal-b1,3-Gal-b1,3-Gal-b1, 4-Glc, GalNAc-b1,3-Gal-b1,4-Glc (GalNAc-b1,3-lactose), Gal-b1,3-GalNAc-b1,3-lactose, GalNAc- b1,3-Gal-a1,4-Gal-b1,4-Glc (globul-N-tetrasaccharide), Gal-b1,3-GalNAc-b1,3-Gal-a1,4-Gal-b1,4-Glc, GalNAc-b1,3-LNT, Gal-b1,3-GalNAc-b1,3-LNT, novo-LNT (GlcNAc-b1,6-[Gal-b1,3]-Gal-b1,4-Glc), Gal-. novo- LNP I (Gal-b1,4-GlcNAc-b1,6-[Gal-b1,3-Gal-b1,3]-Gal-b1,4-Glc), Gal- novo- LNP II (Gal-b1,4-GlcNAc-b1,6-[Gal-b1,3]-Gal-b1,3-Gal-b1,4-Glc), Gal- novo-LNP III (Gal-b1,3-Gal-b1,4-GlcNAc-b1,6-[Gal-b1,3]-Gal-b1,4-Glc), novo-LNO, GalNAc-b1,3-LNnT, Gal-b1,3-GalNAc-b1,3-LNnT, LNH, LNnH, iso-LNO, novo-LNO, novo-LNnO, LND, iso-LND, GalNAc-a1,3-Gal-b1,4-Glc, novo-LNP I, iso-LNT, DGalLNnH, Galili pentasaccharide, lact-N-heptacapaccharide, lact-N-neoheptacapaccharide, p-lacto-N-neoheptacapaccharide, List of para-lacto-N-heptaose, lacto-N-octaose (LNO), lacto-N-neooctaose, iso-lacto-N-octaose, para-lacto-N-octaose, iso-lacto-N-neooctaose, novo-lacto-N-neooctaose, para-lacto-N-neooctaose, iso-lacto-N-nonaose, novo-lacto-N-nonaose, lacto-N-nonaose, lacto-N-decanose, iso-lacto-N-decanose, novo-lacto-N-decanose, and lacto-N-neodecanose.More preferably, the non-fucosylated sugars of the present invention are selected from lacto-N-trisaccharide II (LN3, LNT-II), lacto-N-neotetrasaccharide (LNnT), lacto-N-tetrasaccharide (LNT), p-lacto-N-neopentasaccharide, p-lacto-N-pentasaccharide, lacto-N-neohexasaccharide (LNnH), p-lacto-N-neohexasaccharide (pLNnH), lacto-N-hexasaccharide (LNH), p-lacto-N-hexasaccharide (pLNH), β-(1,3)galactosyl-p-lacto-N-neopentasaccharide, β-(1,4)galactosyl-p-lacto- N-pentasaccharides, Gal-a1,4-Gal-b1,4-Glc (Gal-a1,4-lactose), β3'-galactosyllactose, β6'-galactosyllactose, Gal-a1,4-Gal-a1,4-Gal-b1,4-Glc, Gal-a1,4-Gal-a1,4-Gal-a1,4-Gal-b1,4-Glc, Gal-b1,3-Gal-b1,3-Gal-b1,4-Glc, Gal-b1,3-Gal-b1,3-Ga l-b1,3-Gal-b1,4-Glc,Gal-b1,3-Gal-b1,3-Gal-b1,3-Gal-b1,3-Gal-b1,4-Glc,Gal-b1,3-Gal-b1,3-Gal-b 1,3-Gal-b1,3-Gal-b1,3-Gal-b1,4-Glc, GalNAc-b1,3-Gal-b1,4-Glc (GalNAc-b1,3-lactose), Gal-b1,3-GalNAc- b1,3-Lactose, GalNAc-b1,3-Gal-a1,4-Gal-b1,4-Glc (globul-N-tetrasaccharide), Gal-b1,3-GalNAc-b1,3-Gal-a1,4-Gal-b1,4-Glc , GalNAc-b1,3-LNT, Gal-b1,3-GalNAc-b1,3-LNT, novo-LNT (GlcNAc-b1,6-[Gal-b1,3]-Gal-b1,4-Glc), Gal-. novo- LNP I (Gal-b1,4-GlcNAc-b1,6-[Gal-b1,3-Gal-b1,3]-Gal-b1,4-Glc), Gal- novo- LNP II (Gal-b1,4-GlcNAc-b1,6-[Gal-b1,3]-Gal-b1,3-Gal-b1,4-Glc), Gal- novo-LNP III (Gal-b1,3-Gal-b1,4-GlcNAc-b1,6-[Gal-b1,3]-Gal-b1,4-Glc), novo-LNO, GalNAc-b1,3-LNnT, Gal-b 1,3-GalNAc-b1,3-LNnT, LNH, LNnH, iso-LNO, novo-LNO, novo-LNnO, LND, iso-LND, GalNAc-a1,3-Gal-b1,4-Glc, novo-LNP List of I, iso-LNT, DGalLNnH, Galili pentasaccharide, lact-N-hepta-saccharide, lact-N-neo-hepta-saccharide, para-lact-N-neo-hepta-saccharide, para-lact-N-hepta-saccharide, lact-N-octa-saccharide (LNO), lact-N-neo-octa-saccharide, iso-lact-N-octa-saccharide, para-lact-N-octa-saccharide, iso-lact-N-neo-octa-saccharide, novo-lact-N-neo-octa-saccharide, para-lact-N-neo-octa-saccharide, iso-lact-N-nona-saccharide, novo-lact-N-nona-saccharide, lact-N-nona-saccharide, lact-N-decansaccharide, iso-lact-N-decansaccharide, novo-lact-N-decansaccharide, and lact-N-neo-decansaccharide. More preferably, the non-fucosylated sugars of the present invention are selected from the list consisting of LNT-II, LNT, LNnT, LNH, pLNH, LNnH, pLNnH, LNO, LNnO, pLNO, and pLNnO. More preferably, the non-fucosylated sugars are selected from the list consisting of lacto-N-trisaccharide II (LNT-II), lacto-N-tetrasaccharide (LNT), lacto-N-neotetrasaccharide (LNnT), lacto-N-hexasaccharide (LNH), p-lacto-N-hexasaccharide (pLNH), lacto-N-neohexasaccharide (LNnH), and p-lacto-N-neohexasaccharide (pLNnH). Most preferably, the non-fucosylated sugars are selected from the list consisting of LNT-II, LNT, and LNnT.

[0104] Preferably, the non-fucosylated sugars of the present invention are isolated from microbial culture or fermentation, cell culture, enzymatic reaction, or chemical reaction. Alternatively, the non-fucosylated sugars of the present invention are isolated from natural sources (such as human milk or animal milk, preferably animal milk) by, for example, chromatography or filtration techniques. In additional and / or alternative preferred embodiments, the non-fucosylated sugars of the present invention are produced by cells (preferably single cells) preferably under in vitro and / or in vitro conditions, wherein the cells are preferably selected from a list consisting of free microorganisms, plant cells, animal cells, and protozoan cells. In other words, the non-fucosylated sugars of the present invention are produced from in vitro and / or in vitro cultures of cells, wherein the cells are preferably selected from a list consisting of free microorganisms, plant cells, animal cells, or protozoan cells. Preferably, the cells are microorganisms. Preferably, the microorganisms are selected from a list consisting of bacteria, yeast, and fungi. More preferably, the microorganisms are bacteria, and more preferably, the microorganisms are *Escherichia coli*. Furthermore, preferably, the cells are genetically engineered to produce the non-fucosylated sugars of the present invention.

[0105] In an additional and / or alternative preferred embodiment of the present invention, one or more additional sugars are fucosylated sugars, preferably fucosylated oligosaccharides, more preferably fucosylated lactooligosaccharides, even more preferably fucosylated mammalian lactooligosaccharides, and most preferably fucosylated human lactooligosaccharides. Preferably, the fucosylated sugars / oligosaccharides are neutral fucosylated sugars / oligosaccharides. In view of the excellent results achieved by the method of the present invention, particularly in methods for promoting plant growth and / or development (see the section on "Promoting Growth and / or Development") and methods for protecting plants against abiotic and / or biotic stresses (see the section on "Abiotic and / or Biological Stresses"), it is particularly preferred that one or more additional sugars are fucosylated sugars as described herein.

[0106] "Fucosylated sugars" refer to sugars containing fucose, that is, sugars containing one or more fucose residues. Preferably, the fucosylated sugars of the present invention contain only one fucose, that is, the sugar contains one or more monosaccharides, and only one of the monosaccharides is fucose. "Non-fucosylated" sugars refer to sugars that do not contain fucose. As used herein and as commonly understood in the art, "neutral" sugars refer to sugars that do not carry a negative charge derived from a carboxylic acid group.

[0107] In this regard, a preferred embodiment is that the fucosylated sugar comprises fucose, which is linked to a monosaccharide via an α-1,2-, α-1,3-, or α-1,4-bond, preferably via an α-1,2- or α-1,3-bond, more preferably via an α-1,3-bond, and wherein the monosaccharide is preferably selected from glucose, N-acetylglucosamine, and galactose. In this application and claims, the monosaccharide is more preferably selected from: - Fucose is linked to glucose, N-acetylglucosamine and galactose via α-1,2-bonds, more preferably glucose or galactose, more preferably galactose; - Fucose is linked to glucose, N-acetylglucosamine and galactose via α-1,3-bonds, more preferably glucose or N-acetylglucosamine, more preferably glucose; - Fucose is linked to glucose, N-acetylglucosamine and galactose via α-1,4-bonds, more preferably glucose or N-acetylglucosamine, more preferably N-acetylglucosamine.

[0108] With regard to the method of promoting plant growth and / or development of the present invention (see the section on "Promoting Growth and / or Development"), it is preferred to use fucosylated sugars containing fucose linked to a monosaccharide via an α-1,2-bond, rather than fucosylated sugars containing fucose linked to a monosaccharide via an α-1,3-bond or α-1,4-bond; wherein the monosaccharide is preferably selected from glucose, N-acetylglucosamine, and galactose, more preferably glucose or galactose, and even more preferably galactose. Therefore, when the list of fucosylated sugars listed herein includes α-1,3-fucosylated sugars, α-1,2-fucosylated sugars, and α-1,4-fucosylated sugars, it is also explicitly and unambiguously disclosed, with regard to the method of promoting plant growth and / or development of the present invention, that the same list of sugars not containing α-1,2-linked fucose is also missing.

[0109] With regard to the method of protecting plants against abiotic and / or biotic stresses of the present invention (see the section on "Abiotic and / or Biological Stresses"), fucosylated sugars containing fucose linked to monosaccharides via α-1,2-bonds are preferred, rather than fucosylated sugars containing fucose linked to monosaccharides via α-1,3-bonds or α-1,4-bonds; wherein the monosaccharide is preferably selected from glucose, N-acetylglucosamine, and galactose, more preferably glucose or galactose, and even more preferably galactose. Therefore, when the list of fucosylated sugars listed herein includes α-1,3-fucosylated sugars, α-1,2-fucosylated sugars, and α-1,4-fucosylated sugars, the same list lacking α-1,2-linked fucose is also explicitly and unambiguously disclosed for the method of protecting plants against abiotic and / or biotic stresses of the present invention.

[0110] Those skilled in the art will understand that the expression "fucose linked to monosaccharide" refers to the following situation, wherein fucose is linked to a monosaccharide via a glycosidic bond, and wherein the fucose and monosaccharide are part of the fucoidylated sugars of the present invention (which may include one or more additional monosaccharides in addition to the fucose and the monosaccharide).

[0111] In additional and / or alternative preferred embodiments, the fucosylated sugar is a disaccharide or an oligosaccharide. In a more preferred embodiment, the fucosylated sugar is an oligosaccharide. More preferably, the oligosaccharide consists of 3-12, preferably 3-11, more preferably 3-10, more preferably 3-9, more preferably 3-8, more preferably 3-7, more preferably 3-6, and most preferably 3-5 monosaccharides.

[0112] In a more preferred embodiment, the fucosylated sugars of the present invention are milk sugars (preferably mammalian milk sugars), preferably lactoses, more preferably mammalian lactoses, and most preferably human milk oligosaccharides.

[0113] In additional and / or alternative preferred embodiments, the fucosylated sugar comprises lactose, lacto-N-biose (LNB), or N-acetyllactosamine (LacNAc). Preferably, the fucosylated sugar comprises lactose or LacNAc. More preferably, the fucosylated sugar comprises lactose. Optionally, the sugar further comprises one or more additional monosaccharides, preferably selected from the list consisting of glucose, galactose, N-acetylglucosamine, fucose, and N-acetylgalactosamine, more preferably from the list consisting of glucose, galactose, fucose, and N-acetylglucosamine, and even more preferably from the list consisting of galactose, N-acetylglucosamine, and fucose. More preferably, the fucosylated sugar contains lactose, lacto-N-biose (LNB), or N-acetyllactosamine (LacNAc) at its reducing end. More preferably, the fucosylated sugar contains lactose or LacNAc at its reducing end. More preferably, the fucosylated sugar contains lactose at its reducing end.

[0114] Fucosylated sugars containing lactose at their reducing end are preferably selected from 2'-fucosyllactose (2'FL), 3-fucosyllactose (3-FL), difucosyllactose (diFL), lacto-N-fucopentose I (LNFP I), blood group A antigen hexasaccharide type 1 (GalNAc-LNFP I), blood group B antigen hexasaccharide type 1 (Gal-LNFP I), lacto-N-fucopentose II (LNFPII), lacto-N-fucopentose III (LNFP III), lacto-N-fucopentose V (LNFP V), lacto-N-difucohexasaccharide I (LNDFHI), lacto-N-difucohexasaccharide II (LNDFH II), Lewis b-Lewis x, monofucosyllacto-N-hexasaccharide III (MFLNHIII), and difucosyllacto-N-hexasaccharide (a) (DFLNH (a) a list consisting of difucosyl lact-N-hexasaccharide (DFLNH), trifucosyl lact-N-hexasaccharide (TFLNH), lact-N-neofofucopentose I (LNnFP I), lact-N-neofofucopentose V (LNnFP V, LNFP VI) and lact-N-neodifucohexasaccharide (LNnDFH), more preferably selected from the list consisting of 2'FL, 3-FL, diFL, LNFP I, LNFP II, LNFP III, LNFP V, LNDFH I, LNDFH II, MFLNH III, DFLNH (a), DFLNH, TFLNH, LNnFP I, LNnFP V (LNFP VI) and LNnDFH, more preferably selected from the list consisting of 2'FL, 3-FL, diFL, LNFPI, LNFP II, LNFP III, LNFP V, LNDFH I, LNDFH II, LNnFP I, LNnFP The list consisting of LNFP V (LNFP VI) and LNnDFH is more preferably selected from the list consisting of 2'FL, 3-FL, diFL, LNFP I, LNFP II, LNFP III, LNFP V, LNnFP I and LNnFP V (LNFP VI), more preferably selected from the list consisting of 3-FL, diFL, LNFP III, LNFP V and LNnFP V (LNFP VI), more preferably selected from the list consisting of 3-FL, diFL, LNFP V and LNnFP V (LNFP VI), more preferably selected from the list consisting of 3-FL, LNFP V and LNnFP V (LNFP VI), and most preferably, wherein the fucosylated sugar is 3-FL.

[0115] Fucosylated sugars containing lacto-N-biose (LNB) at their reducing end are preferably selected from the list consisting of 2'-fucosylvobeno-N-biose (2'FLNB), 4-fucosylvobeno-N-biose (4FLNB), and difucosylvobeno-N-biose (diFLNB), more preferably 2'FLNB or diFLNB, and most preferably 2'FLNB.

[0116] Fucosylated sugars containing N-acetyllactosamine (LacNAc) at their reducing end are preferably selected from the list consisting of 2'-fucosyl-N-acetyllactosamine (2'FlacNAc), difucosyl-N-acetyllactosamine (diFLacNAc), and 3-fucosyl-N-acetyllactosamine (3FlacNAc), more preferably 3FlacNAc or diFLacNAc, and most preferably 3'FlacNAc.

[0117] In additional and / or alternative preferred embodiments, the fucosylated sugars of the present invention comprise oligosaccharides selected from the list of 2'FL, 3-FL, 2'FLNB, 4FLNB, 2'FLacNAc, and 3FLacNAc, preferably selected from the list of 2'FL, 3-FL, 2'FLNB, 2'FLAcNAc, and 3FLacNAc, more preferably selected from the list of 3-FL, 2'FL, and 3FLAcNAc, and most preferably 3-FL or 3FLAcNAc; optionally, the oligosaccharides further comprise one or more additional monosaccharides, preferably selected from the list of glucose, galactose, N-acetylglucosamine, N-acetylglucosamine, fucose, and sialic acid, more preferably selected from the list of glucose, galactose, N-acetylglucosamine, N-acetylglucosamine, and fucose, and even more preferably selected from the list of galactose, N-acetylglucosamine, and fucose. For the purposes of this invention, the term "fucosylated sugar comprising an oligosaccharide" refers to a fucosylated sugar containing the oligosaccharide at the reducing end, the non-reducing end, or a position in between of the fucosylated sugar; optionally, the oligosaccharide further comprises one or more additional monosaccharides. In other words, the fucosylated sugar is the same as the oligosaccharide, or has one or more additional monosaccharides at the reducing end of the oligosaccharide and / or has one or more additional monosaccharides at the non-reducing end of the oligosaccharide. For example, LNFP I is a fucosylated sugar containing the oligosaccharide 2'FLNB, which has two additional monosaccharides, namely galactose-β-1,4-glucose, at the reducing end.

[0118] In a more preferred embodiment, the fucoidylated sugar of the present invention comprises an oligosaccharide selected from the list of 2'FL, 3-FL, 2'FLNB, 4FLNB, 2'FLacNAc, and 3FLacNAc, preferably selected from the list of 2'FL, 3-FL, 2'FLNB, 2'FLAcNAc, and 3FLacNAc, more preferably selected from the list of 3-FL, 2'FL, and 3FLAcNAc, and most preferably 3-FL or 3FLAcNAc; optionally, the oligosaccharide further comprises one or more additional monosaccharides, preferably selected from the list of glucose, galactose, N-acetylglucosamine, N-acetylglucosamine, fucose, and sialic acid, more preferably selected from the list of glucose, galactose, N-acetylglucosamine, N-acetylglucosamine, and fucose, and even more preferably selected from the list of galactose, N-acetylglucosamine, and fucose. Preferably, the fucosylated sugar comprises fucose, which is linked to a monosaccharide via α-1,2-, α-1,3-, or α-1,4- bonds, more preferably via α-1,2- or α-1,3- bonds, and more preferably via α-1,3- bonds. The monosaccharide is preferably selected from glucose, N-acetylglucosamine, and galactose. The fucosylated sugar of the present invention also preferably comprises lactose, lact-N-biose (LNB), or N-acetylglucosamine (LacNAc). Preferably, the fucosylated sugar comprises lactose or LacNAc, and most preferably, the fucosylated sugar comprises lactose. More preferably, the fucosylated sugars of the present invention contain lactose, lacto-N-biose (LNB) or N-acetyllactosamine (LacNAc) at their reducing end. Preferably, the fucosylated sugars contain lactose or LacNAc at their reducing end. Most preferably, the fucosylated sugars contain lactose at their reducing end.

[0119] In a more preferred embodiment, the fucosylated sugars of the present invention are selected from 2'-fucosylated lactose (2'FL), 3-fucosylated lactose (3-FL), difucosylated lactose (diFL), 2'-fucosylated-N-acetyllactosamine (2'FlacNAc), difucosylated-N-acetyllactosamine (diFLacNAc), 3-fucosylated-N-acetyllactosamine (3FlacNAc), 2'-fucosylated-N-biose (2'FLNB), 4-fucosylated-N-biose (4FLNB), difucosylated-N-biose (diFLNB), lacto-N-fucopentose I (LNFP I), blood group A antigen hexasaccharide type 1 (GalNAc-LNFP I), blood group B antigen hexasaccharide type 1 (Gal-LNFP I), and lacto-N-fucopentose II (LNFP I). A list consisting of LNFPIII, LNFPV, LNDFHI, LNDFHII, Lewis b-Lewis x, MFLNHIII, DFLNH(a), DFLNH(a), DFLNH, TFLNH, LNnFPI, LNnDFH (LNFP VI), and LNDFH (LNnFH). More preferably, the fucosylated sugars of the present invention are selected from the list consisting of 2'FL, 3-FL, diFL, 2'FlacNAc, diFLacNAc, 3FlacNAc, 2'FLNB, 4FLNB, diFLNB, LNFP I, LNFP II, LNFP III, LNFP V, LNDFHI, LNDFH II, LNnFP I, LNnFP V (LNFP VI), and LNnDFH. More preferably, the fucosylated sugars of the present invention are selected from the list consisting of 2'FL, 3-FL, diFL, 2'FlacNAc, diFLacNAc, 3FlacNAc, 2'FLNB, 4FLNB, diFLNB, LNFP I, LNFP II, LNFP III, LNFP V, LNnFP I, and LNnFP V (LNFP VI). More preferably, the fucosylated sugars of the present invention are selected from the list consisting of 2'FL, 3-FL, diFL, 2'FlacNAc, diFLacNAc, 3FlacNAc, 2'FLNB, diFLNB, LNFP I, LNFP III, LNFP V, LNnFP I and LNnFP V (LNFP VI).More preferably, the fucosylated sugars of the present invention are selected from the list consisting of 3-FL, diFL, diFLacNAc, 3FlacNAc, LNFP III, LNFP V, and LNnFP V (LNFP VI). More preferably, the fucosylated sugars of the present invention are selected from the list consisting of 3-FL, diFL, diFLacNAc, 3FlacNAc, LNFP V, and LNnFP V (LNFP VI). Most preferably, the fucosylated sugars of the present invention are selected from the list consisting of 3-FL, 3FlacNAc, LNFP V, and LNnFP V (LNFP VI).

[0120] For the purposes of this invention, a fucosylated sugar comprising fucose linked to a monosaccharide via an α-1,3-bond; preferably, wherein the monosaccharide is selected from glucose, N-acetylglucosamine, and galactose, more preferably, the monosaccharide is glucose or N-acetylglucosamine, and even more preferably, the monosaccharide is glucose; this is particularly advantageous in the methods of the invention, especially in methods for promoting plant growth and / or development (see the section on “Promoting Growth and / or Development”) and in methods for protecting plants against abiotic and / or biotic stresses (see the section on “Abiotic and / or Biological Stresses”).

[0121] For the purposes of this invention, a fucosylated sugar comprising fucose linked to a monosaccharide via an α-1,2-bond; preferably, wherein the monosaccharide is selected from glucose, N-acetylglucosamine, and galactose, more preferably, wherein the monosaccharide is glucose or galactose, and even more preferably, wherein the monosaccharide is galactose; particularly advantageous in the methods of this invention, especially in methods for promoting plant growth and / or development (see the section on “Promoting Growth and / or Development”) and methods for protecting plants against abiotic and / or biotic stresses (see the section on “Abiotic and / or Biological Stresses”), and even more particularly in methods for protecting plants against abiotic stresses (see the section on “Abiotic and / or Biological Stresses”). Furthermore, the inventors discovered that a fucosylated sugar comprising fucose linked to a monosaccharide via an α-1,2-bond; preferably, wherein the monosaccharide is selected from glucose, N-acetylglucosamine, and galactose; more preferably, the monosaccharide is glucose or galactose; even more preferably, the monosaccharide is galactose; when the sialic acid-containing sugar of the present invention (preferably, wherein the sialic acid is linked to the monosaccharide via an α-2,6-bond, and wherein the monosaccharide is preferably selected from galactose, N-acetylglucosamine, and sialic acid (preferably Neu5Ac), more preferably, the monosaccharide is galactose or N-acetylglucosamine, even more preferably, the monosaccharide is galactose) is also applied to the plant; it can synergistically protect the plant against abiotic stress (especially when the abiotic stress is frost) and / or improve fructification. Furthermore, the inventors discovered that a fucoidylated sugar comprising fucose linked to a monosaccharide via an α-1,2-bond; preferably, wherein the monosaccharide is selected from glucose, N-acetylglucosamine, and galactose; more preferably, the monosaccharide is glucose or galactose; even more preferably, the monosaccharide is galactose; when the sialic acid-containing sugar of the present invention (preferably, wherein the sialic acid is linked to the monosaccharide via an α-2,6-bond, and wherein the monosaccharide is preferably selected from galactose, N-acetylglucosamine, and sialic acid (preferably Neu5Ac), more preferably, the monosaccharide is galactose or N-acetylglucosamine, even more preferably, the monosaccharide is galactose) is also applied to the plant; it can synergistically promote the growth and / or development of the plant.

[0122] Preferably, the fucosylated sugars of the present invention are isolated from microbial culture or fermentation, cell culture, enzymatic reaction, or chemical reaction. Alternatively, the fucosylated sugars of the present invention are isolated from natural sources (such as human milk or animal milk, preferably animal milk) by, for example, chromatography or filtration techniques. In additional and / or alternative preferred embodiments, the fucosylated sugars of the present invention are produced by cells (preferably single cells) preferably under in vitro and / or in vitro conditions, wherein the cells are preferably selected from a list consisting of free microorganisms, plant cells, animal cells, and protozoan cells. In other words, the fucosylated sugars of the present invention are produced from in vitro and / or in vitro cultures of cells, wherein the cells are preferably selected from a list consisting of free microorganisms, plant cells, animal cells, or protozoan cells. Preferably, the cells are microorganisms. Preferably, the microorganisms are selected from a list consisting of bacteria, yeast, and fungi. More preferably, the microorganisms are bacteria, and more preferably, the microorganisms are *Escherichia coli*. Furthermore, preferably, the cells are genetically engineered to produce the fucosylated sugars of the present invention.

[0123] The aforementioned fucosylated sugars are commercially available, and / or methods for their production / purification have been described; therefore, those skilled in the art can accordingly produce / obtain any of the aforementioned fucosylated sugars. For example (each reference is incorporated herein by reference): -2'FL: Zhou et al., 2021, ACS Synth. Biol. 10(3): p. 447-458; Lu et al., 2021, ACS Synth. Biol. 10(5): p. 923-938; WO2022 / 034073; Carbosynth (OF06739) -3-FL: Zhou et al., 2021; ACS Synth. Biol. 10(3): p. 447-458, Lu et al., 2021, ACS Synth. Biol. 10(5): p. 923-938; WO2022 / 034073; Carbosynth (OF05673) -diFL:WO2022 / 034073 -2'FlacNAc:WO2022 / 034075 -3FlacNAc:WO2022 / 034075 -diFLacNAc:WO2022 / 034075 -2'FLNB:WO2022 / 034075 -4FLNB:WO2022 / 034075 -diFLNB:WO2022 / 034075 -LNFP I: Derya et al., 2020, J. biotech. 319: pp. 31-38; Carbosynth (OL05676) -GalNAc-LNFP I: WO2022 / 034077 -Gal-LNFP I:WO2022 / 034077 -LNFP II: Zeuner et al., 2018, ACS Synth. Biol. 10(3): p. 447-458 -LNFP III: Zeuner et al., 2018, ACS Synth. Biol. 10(3): p. 447-458; Carbosynth (OL04212) -LNFP V: WO2020 / 115671; Carbosynth (OL06817) -LNDFH I: Huang et al., 2021, ACS Catal. 11(5): p. 2631-2643; Carbosynth (OL01664) -LNDFH II: Yu et al., 2017, chem. Comm. 53(80): p. 11012-11015; Huang et al., 2021, ACS Catal. 11(5): p. 2631-2643; Carbosynth (OL06826) -MFLNH III: Carbosynth (OM05898) -DFLNH (a): Carbosynth (OD05375) -DFLNH: Carbosynth (OD06532) -TFLNH: Isosep (57 / 18-0010) -LNnFP I: Elicityl (GLY033-2-90%) -LNnFP V: Dumon et al., 2001, Glyconj. J. 18(6): p. 465-474 -LNnDFH: Dumon et al., 2001, Glyconj. J. 18(6): p. 465-474.

[0124] Optionally, in the method of the present invention, one or more additional sugars may be applied, wherein the sugars are monosaccharides. The monosaccharides are preferably selected from the list consisting of sialic acid (preferably as described herein, more preferably Neu5Ac or KDO), galactose, L-fucose, GlcNAc, glucose, GalNAc, xylose, mannose, rhamnose, glucuronic acid, and gluconic acid; more preferably selected from the list consisting of sialic acid (preferably as described herein, more preferably Neu5Ac or KDO), galactose, L-fucose, and glucose; and even more preferably selected from the list consisting of sialic acid (preferably as described herein, more preferably Neu5Ac or KDO), galactose, and L-fucose.

[0125] More preferably, in relation to the method of the present invention, if one or more additional sugars are applied to a plant, a portion of the plant, the seeds of the plant, and / or the intended growth region of the plant in the method of the present invention, then the one or more additional sugars are intermediate sugars as described herein.

[0126] With regard to the method of the present invention, most preferably, if one or more additional sugars are applied to a plant, a portion of the plant, a seed of the plant, and / or a region intended for growth of the plant in the method of the present invention, then the one or more additional sugars are fucosylated sugars as described herein, particularly fucosylated sugars comprising fucose linked to a monosaccharide via an α-1,2- or α-1,3- bond; preferably, wherein the monosaccharide is selected from glucose, N-acetylglucosamine, and galactose.

[0127] In addition, another preferred embodiment is that the amount of any (preferably each) of the additional sugars described herein applied to the plant, parts of the plant, seeds of the plant and / or the intended growth area of ​​the plant is at least 0.10 µg, preferably at least 0.25 µg, more preferably at least 0.50 µg, more preferably at least 1.00 µg, and most preferably at least 1.50 µg. More preferably, the amount of any (preferably each) of the added sugars applied is 0.10 µg-100.00 mg, preferably 0.10 µg-75.00 mg, more preferably 0.10 µg-50.00 mg, more preferably 0.10 µg-25.00 mg, more preferably 0.10 µg-10.00 mg, more preferably 0.10 µg-1.00 mg, more preferably 0.10 µg-100.00 µg, more preferably 0.10 µg-75.00 µg, more preferably 0.25 µg-75.00 µg, more preferably 0.50 µg-75.00 µg, more preferably 1.00 µg-75.00 µg, and most preferably 1.00 µg-50.00 µg. More preferably, the amount of any (preferably each) of the additional sugars applied is at least 0.10 µmol, preferably at least 0.25 µmol, more preferably at least 0.50 µmol, more preferably at least 1.00 µmol, and most preferably at least 1.50 µmol. More preferably, the amount of any (preferably each) of the additional sugars applied is 0.10 µmol-100.00 mmol, preferably 0.10 µmol-75.00 mmol, more preferably 0.10 µmol-50.00 mmol, more preferably 0.10 µmol-25.00 mmol, more preferably 0.10 µmol-10.00 mmol, more preferably 0.10 µmol-1.00 mmol, more preferably 0.10 µmol-100.00 µmol, more preferably 0.10 µmol-75.00 µmol, more preferably 0.25 µmol-75.00 µmol, more preferably 0.50 µmol-75.00 µmol, more preferably 1.00 µmol-75.00 µmol, and most preferably 1.00 µmol-50.00 µmol.

[0128] When the added sugars of the present invention are applied to seeds, it is particularly preferred that the application amount of any (preferably each) of the added sugars is at least 1.00 mg per ton of seeds, preferably at least 5.00 mg, more preferably at least 10.00 mg, more preferably at least 25.00 mg, more preferably at least 50.00 mg, more preferably at least 75.00 mg, and most preferably at least 100.00 mg. More preferably, the application amount of any (preferably each) of the added sugars is 0.001 g to 100.0 g per ton of seeds, preferably 0.010 g to 100.0 g, more preferably 0.025 g to 100.0 g, more preferably 0.050 g to 100.0 g, more preferably 0.050 g to 75.0 g, more preferably 0.075 g to 75.0 g, more preferably 0.100 g to 75.0 g, and most preferably 0.100 g to 60.0 g. More preferably, the amount of any (preferably each) of the additional sugars applied is at least 1.0 µmol per ton of seed, preferably at least 5.0 µmol, more preferably at least 10.0 µmol, more preferably at least 25.0 µmol, more preferably at least 50.0 µmol, more preferably at least 75.0 µmol, more preferably at least 100.0 µmol, and most preferably at least 150.0 µmol. More preferably, the application amount of any (preferably each) of the additional sugars is 1.0 µmol-150.0 mmol per ton of seed, preferably 10.0 µmol-150.0 mmol, more preferably 25.0 µmol-150.0 mmol, more preferably 50.0 µmol-150.0 mmol, more preferably 75.0 µmol-150.0 mmol, more preferably 75.0 µmol-125.0 mmol, more preferably 100.0 µmol-125.0 mmol, more preferably 125 µmol-125.0 mmol, more preferably 150 µmol-125.0 mmol, and most preferably 150 µmol-100.0 mmol.

[0129] In a more preferred embodiment, the amount of any (preferably each) of the additional sugar applied to the plant, parts of the plant, seeds of the plant and / or the intended growth area of ​​the plant is at least 1.0 mg per hectare of the plant, preferably at least 5.0 mg, more preferably at least 10.0 mg, more preferably at least 25.0 mg, more preferably at least 50.0 mg, more preferably at least 75.0 mg, more preferably at least 100.0 mg, and most preferably at least 250.0 mg. More preferably, the application rate of any (preferably each) of the added sugars is 0.001 g-1000.0 g per hectare of the plant, preferably 0.001 g-500.0 g, more preferably 0.001 g-250.0 g, more preferably 0.001 g-100.0 g, more preferably 0.001 g-50.0 g, more preferably 0.001 g-25.0 g, more preferably 0.001 g-10.0 g, more preferably 0.010 g-10.0 g, more preferably 0.025 g-10.0 g, more preferably 0.025 g-7.5 g, more preferably 0.025 g-5.0 g, more preferably 0.050 g-2.5 g, more preferably 0.050 g-1.5 g, more preferably 0.100 g-1.5 g, more preferably 0.100 g-1.25 g, and most preferably 0.250 g-1.25 g.

[0130] In a more preferred embodiment of the invention, the amount of any (preferably each) of the additional sugars applied to the plant, parts of the plant, seeds of the plant, and / or the intended growth area of ​​the plant is at least 1.0 µmol per hectare of the plant, preferably at least 5.0 µmol, more preferably at least 10.0 µmol, more preferably at least 25.0 µmol, more preferably at least 50.0 µmol, more preferably at least 75.0 µmol, more preferably at least 100.0 µmol, more preferably at least 150.0 µmol, more preferably at least 200.0 µmol, and most preferably at least 250.0 µmol. More preferably, the amount of any (preferably each) of the additional sugars applied is 0.001 mmol to 1000.0 mmol, preferably 0.001 mmol to 500.0 mmol, more preferably 0.001 mmol to 250.0 mmol, more preferably 0.001 mmol to 100.0 mmol, more preferably 0.001 mmol to 50.0 mmol, more preferably 0.001 mmol to 25.0 mmol, more preferably 0.001 mmol to 10.0 mmol, more preferably 0.010 mmol to 10.0 mmol, more preferably 0.025 mmol to 10.0 mmol, more preferably 0.025 mmol to 7.5 mmol, more preferably 0.025 mmol to 5.0 mmol, more preferably 0.050 mmol to 2.5 mmol, more preferably 0.050 mmol to 2.0 mmol, more preferably 0.075 mmol to 2.0 mmol, more preferably 0.100 mmol. mmol-2.0 mmol, with the optimal range being 0.100 mmol-1.50 mmol.

[0131] In another preferred embodiment, any (preferably all) of the added sugars are present in the form of agronomically acceptable salts.

[0132] Suitable salts include, but are not limited to, salts of acceptable inorganic acids, such as salts of hydrochloric acid, sulfuric acid, phosphoric acid, nitric acid, carbonic acid, boric acid, aminosulfonic acid, and hydrobromic acid, or salts of agronomically acceptable organic acids, such as acetic acid, propionic acid, butyric acid, tartaric acid, maleic acid, hydroxymaleic acid, fumaric acid, malic acid, citric acid, lactic acid, viscous acid, gluconic acid, benzoic acid, succinic acid, oxalic acid, phenylacetic acid, methanesulfonic acid, toluenesulfonic acid, benzenesulfonic acid, salicylic acid, sulfanilic acid, aspartic acid, glutamic acid, ethylenediaminetetraacetic acid, stearic acid, palmitic acid, oleic acid, lauric acid, pantothenic acid, tannic acid, ascorbic acid, and valeric acid. Suitable salts also include salts of inorganic and organic bases, such as salts of counterions like sodium, calcium, potassium, lithium, magnesium, nickel, zinc, iron, selenium, ammonium, and trimethylsulfonium. These compounds may also be obtained, stored, and / or used in the form of N-oxides. In addition, it includes acid addition salts or base salts, wherein the counterion is optically active, such as d-lactate or l-lysine, or is a racemic mixture, such as dl-tartrate or dl-arginine.

[0133] In another preferred embodiment of the invention, the fucosylated sugars and optionally any (preferably all) additional fucosylated sugars are linked (preferably chemically linked) to a carrier for delivery of the fucosylated sugars. In additional and / or alternative preferred embodiments, the non-fucosylated sugars and optionally any (preferably all) additional non-fucosylated sugars are linked (preferably chemically linked) to a carrier for delivery of the fucosylated sugars. In additional and / or alternative preferred embodiments, the additional sugars and optionally any (preferably all) additional additional sugars are linked (preferably chemically linked) to a carrier for delivery of the additional sugars. The linking of the sugars to the carrier can improve their affinity. Preferably, the carrier is a ceramide-based carrier or a peptide-based carrier, more preferably, the carrier is a ceramide-based carrier. Preferably, the peptide-based carrier is ε-polylysine, α-polylysine, polyaspartic acid, polyglutamic acid, or polyornithine. These carriers are commercially available (e.g., Sigma-Aldrich, Carbosynth). The ceramide-based carriers are preferably selected from the list consisting of d18:1 / 16:0, t18:0-16:0, t18:0-h16:0, t18:0-h22:0, and t18:0-h24:0. These ceramide carriers are commercially available and well known to those skilled in the art, for example, as described in WO2010 / 037785, which is incorporated herein by reference. d18:1 / 16:0 is also known as C16 ceramide and N-palmitoylsphingosine, and therefore can be used interchangeably herein. t18:0-16:0 is also known as C16 phytoceramide and N-hexadecanoylphytosphingosine, and therefore can be used interchangeably herein. t18:0-h16:0, t18:0-h22:0, and t18:0-h24:0 are glycosylinositol phosphoceramide (GIPC). As those skilled in the art will know, “d” and “t” refer to the hydroxylation state of the entire ceramide or long-chain base moiety (d is 2 groups, t is 3 groups), while “h” indicates the hydroxylation of fatty acyl groups.

[0134] Composition In a preferred embodiment of the invention, the sialic acid-containing sugars of the invention (see the section "Sialic Acid-Containing Sugars") are part of the composition. Therefore, a preferred method is a method of treating plants, wherein the method includes applying the composition to the plant, parts of the plant, seeds of the plant, and / or the intended growth area of ​​the plant, wherein the composition comprises sialic acid-containing sugars with a degree of polymerization (DP) of at least 2 (see the section "Sialic Acid-Containing Sugars").

[0135] In an additional and / or alternative preferred embodiment, any one or more (preferably all) additional sugars (see the “Additional Sugars” section) applied to the plant, parts of the plant, seeds of the plant, and / or the intended growth area of ​​the plant are part of the composition in the method of the invention.

[0136] For the purposes of this invention, each of the sugars of the invention applied to the plant, a portion of the plant, the seed of the plant, and / or the intended growth area of ​​the plant is preferably part of the same composition.

[0137] In a more preferred embodiment, the composition further comprises one or more selected from the list of emulsifiers, solvents, surfactants, carriers, dispersants, thickeners, hydrophobic agents, water-retaining agents, thickeners, solid carriers, foaming agents, antifreeze agents, and defoamers.

[0138] In additional and / or alternative preferred embodiments, the composition is selected from the list of solutions, emulsions, suspensions, powders, dusts, foams, pastes, particles, aerosols, microcapsules, compressed formulations, capsules, and fogging formulations (cold fog or hot fog).

[0139] More preferably, the composition of the present invention is an agricultural chemical composition, that is, a composition suitable for agricultural use (agricultural composition), and more preferably a composition suitable for industrial agricultural use (industrial agricultural composition).

[0140] More preferably, the composition is a synthetic composition, that is, a composition that does not exist in nature and / or a composition in which at least one component is a synthetic component.

[0141] In the compositions of the present invention, preferably, the concentration of the sialic acid-containing sugars (see the section "Sialic Acid-Containing Sugars") is at least 0.000001% (w / w) of the total weight of the composition, more preferably at least 0.00001%, more preferably at least 0.00005%, and most preferably at least 0.0001% (w / w). Additionally and / or alternatively, the concentration of the sialylated sugars is ≤50.0% (w / w) of the total weight of the composition, preferably ≤40.0%, more preferably ≤30.0%, more preferably ≤20.0%, more preferably ≤10.0%, more preferably ≤5.0%, and most preferably ≤1.0% (w / w). More preferably, the concentration of the sialylated sugars in this invention is 0.000001-50.0% of the total weight of the composition, preferably 0.000001-10.0%, more preferably 0.000001-5.0%, even more preferably 0.00001-5.0%, and most preferably 0.00001-1.0% (w / w).

[0142] In this application and claims, unless otherwise expressly specified, the terms "wt.%" and "% (w / w)" are used interchangeably and both refer to weight percentage. For example, if the composition is a solid composition, 1.0 wt.% means that 1.0 g of sugar is contained in 100.0 g of the solid composition. For example, if the composition is a liquid composition, 1.0 wt.% means that 1.0 g of sugar is contained in 100.0 g of the liquid composition.

[0143] In the compositions of the present invention, preferably, the concentration of any (preferably all) additional sugars (if any) (see the “Additional Sugars” section) is at least 0.000001% (w / w) of the total weight of the composition, more preferably at least 0.00001%, more preferably at least 0.00005%, and most preferably at least 0.0001% (w / w). Additionally and / or alternatively, the concentration of said any (preferably all) additional sugars is ≤50.0% (w / w) of the total weight of the composition, more preferably ≤40.0%, more preferably ≤30.0%, more preferably ≤20.0%, more preferably ≤10.0%, more preferably ≤5.0%, and most preferably ≤1.0% (w / w). More preferably, the concentration of any (preferably all) additional sugar is 0.000001-50.0% of the total weight of the composition, preferably 0.000001-10.0%, more preferably 0.000001-5.0%, even more preferably 0.00001-5.0%, and most preferably 0.00001-1.0% (w / w).

[0144] Promoting growth and / or development In a preferred embodiment of the first aspect, the method of the present invention is a method for promoting the growth and / or development of a plant or a part of a plant (preferably a flower or fruit), wherein the method includes the step of applying a sialic acid-containing sugar to the plant, a part of the plant, a seed of the plant, and / or a desired growth area of ​​the plant, wherein the degree of polymerization (DP) of the sialic acid-containing sugar is at least 2. Preferably, the plant is under physiological conditions, abiotic stress, or biotic stress.

[0145] For the purposes of this invention, the term “promote” may be used interchangeably with “improve”, and, in relation to plant growth and / or development, it means that the growth and / or development of a plant is generally improved in one or more characteristics or parameters of plant growth and / or plant development compared to a control plant (i.e., a plant that has not received the sialic acid-containing sugars described in this invention (optionally, any additional sugars as described in the “Additional Sugars” section)).

[0146] For the purposes of this invention, the term "promoting growth and / or development" preferably refers to one or more of the following: improving plant yield (i.e., biomass), improving fruiting capacity, improving flower development, and improving resilience (i.e., vigor, vitality). The method of this invention is also particularly effective in improving flower development.

[0147] Plant yield refers to the biomass of a plant or one or more parts of a plant, which may include aboveground parts (preferably harvestable parts) and / or underground parts (preferably harvestable parts). Preferably, plant yield includes one or more of the following: number of roots, root mass, root volume, leaf area, stem length, stem mass, number of fruits, and fruit mass; all of which can be readily assessed by those skilled in the art using conventional techniques. Alternatively, the plant yield preferably refers to the fresh or dry weight of the whole plant, preferably the fresh or dry weight of the plant canopy (i.e., the aboveground part of the plant). More preferably, the plant yield is assessed by measuring stem length or stem mass, and even more preferably, by measuring stem length. Compared to untreated plants (i.e., plants not treated with the sialic acid-containing sugars of the present invention and optionally additional sugars), improved plant yield preferably refers to an increase in plant stem length or weight (dry or fresh, preferably fresh) or canopy weight (dry or fresh, preferably fresh), preferably an increase in stem length of at least 1.0%, preferably at least 2.5%, more preferably at least 5.0%, and most preferably at least 7.5%.

[0148] Fruiting capacity relates to the fruit growth process, including the number of fruits, fruit size, fruit weight, and fruit quality. Preferably, the fruiting capacity is assessed by counting the number of fruits of the plant and / or calculating the average fruit weight of the plant.

[0149] Flower development involves the developmental process of a flower, including the number of flowers, flower size, flower weight, and flower quality. Preferably, flower development is assessed by counting the number of healthy, normal flowers.

[0150] The strength of a plant can be assessed by examining its uprightness. Alternatively, an increase in the ratio of stem weight to stem length also indicates an increase in the plant's strength. In this application and claims, mass (i.e., weight) can be fresh weight or dry weight, preferably fresh weight.

[0151] The terms “method,” “plant,” “application,” “sialic acid-containing sugars,” “plant parts,” and “regions” are as described above (see the sections “methods of treating plants,” “plants,” “sialic acid-containing sugars,” “additional sugars,” and “compositions”).

[0152] In a more preferred embodiment, the sialic acid-containing sugar is as disclosed in the section “Sialic Acid-Containing Sugars”.

[0153] In a more preferred embodiment, the sialic acid-containing carbohydrate of the present invention comprises sialic acid linked to a monosaccharide via an α-2,6-bond (preferably, the sialic acid is 9-carbon sialic acid or 8-carbon sialic acid, more preferably 9-carbon sialic acid, more preferably Neu5Ac); preferably, the monosaccharide is selected from galactose, N-acetylglucosamine and sialic acid, more preferably, the monosaccharide is galactose or N-acetylglucosamine, more preferably, the monosaccharide is galactose.

[0154] In a more preferred embodiment, the sialic acid-containing sugar comprises an oligosaccharide selected from the list of 6'SL, 6'SLNB, 6'SLAcNAc, 6'KDO-lactose, 6'KDO-LNB, and 6'KDO-LacNAc, preferably selected from the list of 6'SL, 6'SLNB, 6'SLAcNAc, and 6'KDO-lactose, and most preferably selected from the list of 6'SL, 6'SLNB, and 6'SLAcNAc; optionally, the oligosaccharide further comprises one or more additional monosaccharides, preferably selected from the list of glucose, galactose, N-acetylglucosamine, N-acetylglucosamine, fucose, and sialic acid, more preferably selected from the list of glucose, galactose, N-acetylglucosamine, fucose, and sialic acid, more preferably selected from the list of galactose, N-acetylglucosamine, fucose, and sialic acid, and most preferably selected from the list of galactose, N-acetylglucosamine, and fucose.

[0155] In additional and / or alternative preferred embodiments, the sialic acid-containing sugar comprises lactose, lacto-N-biose (LNB), or N-acetyllactosamine (LacNAc). Preferably, the sialic acid-containing sugar comprises lactose or LacNAc. Most preferably, the sialic acid-containing sugar comprises lactose. Optionally, the sugar further comprises one or more additional monosaccharides, preferably selected from the list consisting of glucose, galactose, N-acetylglucosamine, N-acetylgalactosamine, fucose, and sialic acid. More preferably, the list consisting of glucose, galactose, N-acetylglucosamine, fucose, and sialic acid is selected. More preferably, the list consisting of galactose, N-acetylglucosamine, fucose, and sialic acid is selected. Most preferably, the list consisting of galactose, N-acetylglucosamine, and fucose is selected. More preferably, the sialic acid-containing sugar contains lactose, lacto-N-biose (LNB), or N-acetyllactosamine (LacNAc) at its reducing end. Preferably, the sialic acid-containing sugar contains lactose or LacNAc at its reducing end. Most preferably, the sialic acid-containing sugar contains lactose at its reducing end.

[0156] In a more preferred embodiment, the sialylated sugar is selected from 6'-sialyl lactose (6'SL), 3,6-disialyl lactose, 6,6'-disialyl lactose, 6'S-2'FL, 6'S-3-FL, Neu5Ac-α-2,6-(GlcNAc-β-1,3-)Gal-β-1,4-Glc, Neu5Ac-α-2,6-(Neu5Ac-α-2,3-)Gal-β-1,4-Glc, LST b, LST c. Disialial lacto-N-tetrasaccharide (DSLNT), disialial lacto-N-tetrasaccharide analog (DS'LNT), disialial lacto-N-neotetrasaccharide (DSLNnT), disialial lacto-N-neotetrasaccharide analog (DS'LNnT), 6'-sialial lacto-N-disaccharide (6'SLNB), 6'-sialyllactosamine (6'SLacNAc), 6'KDO-lactose, 6'KDO-LNB, and 6'KD A list of O-LacNAc components; more preferably, 6'-sialyl lactose (6'SL), 3,6-disialial lactose, 6'S-2'FL, 6'S-3-FL, Neu5Ac-α-2,6-(GlcNAc-β-1,3-)Gal-β-1,4-Glc, Neu5Ac-α-2,6-(Neu5Ac-α-2,3-)Gal-β-1,4-Glc, LST b, LST c, bis(sialyllact-N-tetrasaccharide) (DSLNT), bis(sialyllact-N-tetrasaccharide) analog (DS'LNT), bis(sialyllact-N-neotetrasaccharide) (DSLNnT), bis(sialyllact-N-neotetrasaccharide) analog (DS'LNnT), 6'-sialyllact-N-disaccharide (6'SLNB), 6'-sialyllactosamine (6'SLacNAc), 6'KDO-lactose, 6'KDO-LNB and 6'KDO-LacNAc; more preferably selected from the list consisting of 6'-sialyllactose (6'SL), 6'S-2'FL, 6'S-3-FL, Neu5Ac-α-2,6-(GlcNAc-β-1,3-)Gal-β-1,4-Glc, LST b, LST c. A list consisting of DSLNnT, DS'LNT, 6'-sialyl-lact-N-biose (6'SLNB), 6'-sialyl-lactosamine (6'SLacNAc), 6'KDO-lactose, 6'KDO-LNB, and 6'KDO-LacNAc; more preferably, a list consisting of 6'-sialyl-lactose (6'SL), LSTb, LSTc, 6'-sialyl-lact-N-biose (6'SLNB), 6'-sialyl-lactosamine (6'SLacNAc), 6'KDO-lactose, 6'KDO-LNB, and 6'KDO-LacNAc;More preferably, the list consisting of 6'-sialyl lactose (6'SL), LST b, LST c, 6'-sialyl lacto-N-biose (6'SLNB), 6'-sialyl lactosamine (6'SLacNAc), 6'KDO-lactose, 6'KDO-LNB, and 6'KDO-LacNAc is selected; more preferably, the list consisting of 6'-sialyl lactose (6'SL), LST b, LST c, 6'-sialyl lacto-N-biose (6'SLNB), 6'-sialyl lactosamine (6'SLacNAc), and 6'KDO-lactose is selected; more preferably, the list consisting of 6'-sialyl lactose (6'SL), LST b, LST c, 6'-sialyl lacto-N-biose (6'SLNB), and 6'-sialyl lactosamine (6'SLacNAc) is selected; more preferably, the list consisting of 6'-sialyl lactose (6'SL), LST b, LST c, 6'-sialyl lacto-N-biose (6'SLNB), and 6'-sialyl lactosamine (6'SLacNAc) is selected; more preferably, the list consisting of 6'-sialyl lactose (6'SL), LST b, LST c, 6'-sialyl lacto-N-biose (6'SLNB), and 6'-sialyl lactosamine (6'SLacNAc) is selected. A list consisting of b and LST c; the optimal choice is 6'SL or LST c.

[0157] As detailed in the "Additional Sugars" section, in the method of the present invention, one or more additional sugars are optionally applied, preferably one or more additional oligosaccharides, more preferably one or more additional lactooligosaccharides, even more preferably one or more additional mammalian lactooligosaccharides, and most preferably one or more additional human lactooligosaccharides. The one or more additional sugars may be sialylated sugars as described in the "Sialic Acid-Containing Sugars" section. Alternatively and additionally, the one or more additional sugars may be sialic acid as described in the "Additional Sugars" section. Alternatively and additionally, the one or more additional sugars may be intermediate sugars as described in the "Additional Sugars" section. Alternatively and additionally, the one or more additional sugars may be non-fucosylated sugars as described in the "Additional Sugars" section. Alternatively and additionally, the one or more additional sugars may be fucosylated sugars as described in the "Additional Sugars" section. Alternatively and additionally, the one or more additional sugars may be monosaccharides as described in the "Additional Sugars" section.

[0158] In particular, for the purpose of promoting growth and / or development, one or more of the additional sugars are fucosylated sugars.

[0159] In a more preferred embodiment, the one or more additional sugars are fucosylated sugars comprising fucose linked to a monosaccharide via an α-1,2-bond; preferably, the monosaccharide is selected from glucose, N-acetylglucosamine, and galactose; more preferably, the monosaccharide is glucose or galactose; and even more preferably, the monosaccharide is galactose.

[0160] Preferably, the fucosylated sugar comprises an oligosaccharide selected from 2'FL, 2'FLNB, and 2'FLacNAc; optionally, the oligosaccharide further comprises one or more additional monosaccharides, preferably selected from the list consisting of glucose, galactose, N-acetylglucosamine, N-acetylglucosamine, fucose, and sialic acid, more preferably selected from the list consisting of glucose, galactose, N-acetylglucosamine, N-acetylglucosamine, and fucose.

[0161] More preferably, the fucosylated sugar comprises lactose, lacto-N-biose (LNB), or N-acetyllactosamine (LacNAc). Preferably, the fucosylated sugar comprises lactose or LacNAc. Most preferably, the fucosylated sugar comprises lactose. Optionally, the sugar further comprises one or more additional monosaccharides, preferably selected from the list consisting of glucose, galactose, N-acetylglucosamine, fucose, and N-acetylgalactosamine. More preferably, the monosaccharides are selected from the list consisting of glucose, galactose, fucose, and N-acetylglucosamine. More preferably, the fucosylated sugar comprises lactose, lacto-N-biose (LNB), or N-acetyllactosamine (LacNAc) at its reducing end. Preferably, the fucosylated sugar comprises lactose or LacNAc at its reducing end. Most preferably, the fucosylated sugar comprises lactose at its reducing end.

[0162] More preferably, the fucosylated sugars are selected from 2'-fucosyllactose (2'FL), difucosyllactose (diFL), 2'-fucosyl-N-acetyllactosamine (2'FlacNAc), difucosyl-N-acetyllactosamine (diFLacNAc), 2'-fucosyllacto-N-biose (2'FLNB), difucosyllacto-N-biose (diFLNB), lacto-N-fucopentose I (LNFP I), blood group A antigen hexasaccharide type 1 (GalNAc-LNFP I), blood group B antigen hexasaccharide type 1 (Gal-LNFP I), lacto-N-difucohexasaccharide I (LNDFH I), Lewis b-Lewis x, difucosyllacto-N-hexasaccharide(a) (DFLNH (a)), trifucosyllacto-N-hexasaccharide (TFLNH), and lacto-N-neofucopentose I (LNnFP The list consists of I). More preferably, the fucosylated sugars of the present invention are selected from the list consisting of 2'FL, diFL, 2'FlacNAc, diFLacNAc, 2'FLNB, diFLNB, LNFPI, LNDFH I, and LNnFP I. More preferably, the fucosylated sugars of the present invention are selected from the list consisting of 2'FL, diFL, 2'FlacNAc, diFLacNAc, 2'FLNB, diFLNB, LNFP I, and LNnFP I. Most preferably, the fucosylated sugars of the present invention are selected from the list consisting of 2'FL, diFL, LNFP I, and LNnFP I.

[0163] In a preferred embodiment of the addition and / or alternative, the one or more additional sugars are fucosylated sugars comprising fucose linked to a monosaccharide via an α-1,3-bond; preferably, the monosaccharide is selected from glucose, N-acetylglucosamine and galactose, more preferably, the monosaccharide is glucose or N-acetylglucosamine, and even more preferably, the monosaccharide is glucose.

[0164] Preferably, the fucosylated sugar comprises oligosaccharides selected from 3-FL and 3FLacNAc; optionally, the oligosaccharides further comprise one or more additional monosaccharides, the monosaccharides preferably being selected from the list consisting of glucose, galactose, N-acetylglucosamine, N-acetylglucosamine, fucose and sialic acid, more preferably being selected from the list consisting of glucose, galactose, N-acetylglucosamine, N-acetylglucosamine and fucose.

[0165] More preferably, the fucosylated sugar comprises lactose, lacto-N-biose (LNB), or N-acetyllactosamine (LacNAc). More preferably, the fucosylated sugar comprises lactose or LacNAc. Most preferably, the fucosylated sugar comprises lactose. More preferably, the fucosylated sugar comprises lactose, lacto-N-biose (LNB), or N-acetyllactosamine (LacNAc) at its reducing end. More preferably, the fucosylated sugar comprises lactose or LacNAc at its reducing end. Most preferably, the fucosylated sugar comprises lactose at its reducing end.

[0166] More preferably, the fucosylated sugars are selected from the list consisting of 3-fucosyllactose (3-FL), difucosyllactose (diFL), difucosyl-N-acetyllactosamine (diFLacNAc), 3-fucosyl-N-acetyllactosamine (3FlacNAc), lacto-N-fucopentose III (LNFP III), lacto-N-fucopentose V (LNFP V), lacto-N-difucohexasose II (LNDFH II), Lewis b-Lewis x, monofucosyl lacto-N-hexasose III (MFLNH III), difucosyl lacto-N-hexasose (a) (DFLNH (a)), difucosyl lacto-N-hexasose (DFLNH), trifucosyl lacto-N-hexasose (TFLNH), lacto-N-neofucopentose V (LNnFP V, LNFP VI) and lacto-N-neodifucohexasose (LNnDFH). More preferably, the fucosylated sugars of the present invention are selected from the list consisting of 3-FL, diFL, diFLacNAc, 3FlacNAc, LNFP III, LNFPV, LNDFH II, LNnFP V (LNFP VI), and LNnDFH. More preferably, the fucosylated sugars of the present invention are selected from the list consisting of 3-FL, diFL, diFLacNAc, 3FlacNAc, LNFP III, LNFP V, and LNnFP V (LNFP VI). More preferably, the fucosylated sugars of the present invention are selected from the list consisting of 3-FL, diFL, diFLacNAc, 3FlacNAc, LNFP V, and LNnFP V (LNFP VI). Most preferably, the fucosylated sugars of the present invention are selected from the list consisting of 3-FL, 3FlacNAc, LNFP V, and LNnFP V (LNFP VI).

[0167] In another preferred embodiment, an effective amount of the sialic acid-containing sugars of the present invention is applied to the plant, parts of the plant, seeds of the plant, and / or the intended growth area of ​​the plant. The term "effective amount" refers to the amount required to achieve an improvement in one or more characteristics or parameters of plant growth and / or plant development compared to a control plant. As will be understood by those skilled in the art, the effective amount can vary depending on factors such as the plant species or variety treated, the presence of abiotic and / or biotic stresses, the desired outcome, the plant's growth stage, and the application site (e.g., leaves, roots, or seeds). Those skilled in the art can readily determine the appropriate effective amount in any given situation. If one or more additional sugars are applied in the method of the present invention, it is preferable to apply an effective amount of any one (preferably all) of the additional sugars. For inventions involving the application of at least one additional sugar to the plant, a portion of the plant, the seeds of the plant, and / or the intended growth region of the plant in methods for promoting plant growth and / or development, it is particularly preferred that each sialic acid-containing sugar and each additional sugar (preferably, one or more of the additional sugars are fucosylated sugars) are applied in a synergistic amount. As will be understood by those skilled in the art, a “synergistic amount” of sugar refers to the amount of sugar capable of producing a synergistic effect. For the purposes of this invention, the synergistic effect refers to a promoting effect on plant growth and / or development that is greater than the promoting effect on plant growth and / or development observed when the sugars are applied alone.

[0168] In additional and / or preferred embodiments, a non-phytotoxic amount of the sialic acid-containing sugars of the present invention is applied to the plant. If one or more additional sugars are applied in the method of the present invention, it is preferred to apply any one (preferably all) of the additional sugars in a non-phytotoxic amount. For clarity, the term "non-phytotoxic" applies to the treated plant, i.e., the one or more sugars applied are non-toxic to the treated plant (or at least, according to the art, their toxicity level is acceptable).

[0169] In a more preferred embodiment, the amount of the sialic acid-containing sugars and (if present) any (preferably all) additional sugars are as described in the sections “Sialic Acid-Containing Sugars” and “Additional Sugars”.

[0170] Abiotic stress and / or biotic stress In a preferred embodiment of the first aspect, the method of the present invention is a method for protecting a plant or a part of a plant (preferably a flower or fruit) against abiotic and / or biotic stresses, wherein the method comprises applying a sialic acid-containing sugar to the plant, a part of the plant, a seed of the plant, and / or a region intended for growth of the plant, wherein the degree of polymerization (DP) of the sialic acid-containing sugar is at least 2. The method protects the plant as a result in the plant being able to tolerate abiotic and / or biotic stresses. In view of the excellent results achieved, a particularly preferred embodiment is that the method of the present invention is a method for protecting the flower of a plant against abiotic and / or biotic stresses (preferably abiotic stresses). In other words, preferably, the method is a method for protecting the flower of a plant against abiotic and / or biotic stresses (preferably abiotic stresses).

[0171] For the purposes of this invention, the term "stress" preferably refers to any condition or substance that has a negative impact on plant growth, development, and / or metabolism. When the condition / substance has living properties, it is called "biotic stress" (Gull et al., 2019, IntechOpen, Abiotic and biotic stress in plants, Chapter 1, pp. 1-19). When the condition / substance has non-living properties (e.g., physical and / or chemical properties), it is called "abiotic stress" (Gull et al., 2019, IntechOpen, Abiotic and biotic stress in plants, Chapter 1, pp. 1-19).

[0172] In relation to this invention (i.e., abiotic stress, biotic stress, or abiotic stress and biotic stress), the term "protection" is preferably replaced by the expression "control, prevention, or treatment," and more preferably by the expression "prevention or treatment." Regarding abiotic stress, the term "protection" is more preferably replaced by the term "prevention." As understood by those skilled in the art, the term "control" preferably refers to reducing the degree / severity of abiotic and / or biotic stress; eliminating said abiotic and / or biotic stress; and / or preventing damage or further damage caused by said abiotic and / or biotic stress. For the purposes of this invention, the term "treatment" preferably refers to suppressing the abiotic and / or biotic stress, i.e., preventing the development of the abiotic and / or biotic stress; alleviating the abiotic and / or biotic stress, i.e., causing the abiotic and / or biotic stress to subside; and / or alleviating the condition caused or resulting from the abiotic and / or biotic stress, i.e., alleviating, preventing, or treating the symptoms of the abiotic and / or biotic stress. In other words, "treatment" preferably refers to reducing the duration (number of days / weeks / months of exposure to the abiotic and / or biotic stress), risk, complications, and / or severity of the abiotic and / or biotic stress; this also includes alleviating the symptoms caused by the abiotic and / or biotic stress. The term "prevention" preferably refers to avoiding the occurrence of the abiotic and / or biotic stress, and / or reducing the incidence of the abiotic and / or biotic stress. In other words, "prevention" preferably refers to mitigating the risk of exposure to the abiotic and / or biotic stresses. In this application and claims, unless otherwise expressly stated, the term "prevention" is preferably replaced by the term "priming," that is, a mechanism that brings a plant to a physiological state such that the plant can respond more quickly and / or more robustly after exposure to abiotic and / or biotic stresses.

[0173] The terms “method,” “plant,” “application,” “sialic acid-containing sugars,” “plant parts,” and “regions” are as described above (see the sections “methods of treating plants,” “plants,” “sialic acid-containing sugars,” “additional sugars,” and “compositions”).

[0174] In a more preferred embodiment, the abiotic stress is selected from a list consisting of frost, drought, osmotic stress (preferably salinity), humidity (preferably flooding), heat stress, light stress (preferably ultraviolet stress), and mechanical stress; preferably selected from a list consisting of frost, drought, osmotic stress (preferably salinity), humidity (preferably flooding), heat stress, and light stress (preferably ultraviolet stress); more preferably selected from a list consisting of frost, drought, osmotic stress (preferably salinity), humidity (preferably flooding), and light stress (preferably ultraviolet stress); even more preferably selected from a list consisting of frost, drought, osmotic stress (preferably salinity), and humidity (preferably flooding); and most preferably selected from a list consisting of frost, drought, and humidity (preferably flooding).

[0175] The term "flooding," well known to those skilled in the art, refers to a situation where at least the plant root system is submerged for an extended period. As is known to those skilled in the art, the duration required to achieve a flooded state depends on the plant species, but is preferably at least 1 day, more preferably at least 2 days, more preferably at least 3 days, more preferably at least 4 days, more preferably at least 5 days, more preferably at least 6 days, and most preferably at least 7 days. Flooding is characterized by a lack of oxygen and carbohydrates. For clarity, flooding does not include ponding (e.g., swamps) or inundation (dry areas permanently submerged underwater). In other words, "flooding" refers to a situation where a dry area is temporarily submerged (preferably at least 1 day, more preferably at least 2 days, more preferably at least 3 days, more preferably at least 4 days, more preferably at least 5 days, more preferably at least 6 days, and most preferably at least 7 days), periodically submerged, or intermittently submerged.

[0176] The scope of this invention also includes the following situations: the abiotic stress is one or more of frost, drought, osmotic stress (preferably salt), humidity (preferably flooding), heat stress, light stress (preferably ultraviolet stress), and mechanical stress; preferably, one or more of frost, drought, osmotic stress (preferably salt), humidity (preferably flooding), heat stress, and light stress (preferably ultraviolet stress); more preferably, one or more of frost, drought, osmotic stress (preferably salt), humidity (preferably flooding), and light stress (preferably ultraviolet stress); even more preferably, one or more of frost, drought, osmotic stress (preferably salt), and humidity (preferably flooding); most preferably, one or more of frost, drought, and humidity (preferably flooding).

[0177] In another preferred embodiment, the biotic stress comprises (preferably composed of) a plant pathogen, i.e., an organism pathogenic to the plant. The plant pathogen preferably directly damages the plant and / or causes disease in the plant, more preferably causing disease in the plant. Therefore, the biotic stress preferably comprises (preferably composed of) a plant pathogen or a disease caused by the plant pathogen, more preferably comprising (preferably composed of) a disease caused by the plant pathogen. Preferably, the plant pathogen is selected from the list of fungi, bacteria, viruses, nematodes, mollusks, and insects. More preferably, the plant pathogen is selected from the list of fungi, bacteria, viruses, nematodes, and insects. More preferably, the plant pathogen is selected from the list of fungi, bacteria, and viruses. More preferably, the plant pathogen is a fungus or a bacterium. Most preferably, the plant pathogen is a fungus.

[0178] The plant pathogenic fungi are preferably selected from the list consisting of the following genera: *Albugo*, *Alternaria*, *Aphanomyces*, *Ascochyta*, *Aspergillus*, *Blumeria*, *Botrytis*, *Bremia*, *Ceratocystsc*, *Cercospora*, *Cladiosporium*, *Cladosporium*, *Claviceps*, and *Cercospora*. Cochliobolus, Colletotrichum, Corticium, Cycloconium, Diaporthe, Elsinoe, Eutypa, Exobasidium, Fomitiporia, Fusarium, Gaeumannomyces, Ganoderma, Gibberella, Gloeosporiu m), Glomerella, Guigardia, Gymnosporangium, Helminthospohum, Helminthosporium, Hemileia, Leptosphaeria, Macropomina, Magnaporthe, Mildew, Monilinia, Monographella, Mycosphaer ella), Nectria, Oomycete, Penicillium, Peronospora, Phaemonella, Phaeoacremonium, Phaeosphaera, Phakopsora, Phona, Phopsis, Phytophthora, Plasmodiophora, Plasmopara, and Forsythoside(Podosphaera), *Pseudoperonospora*, *Puccinia*, *Pyrenopeziza*, *Pyrenophora*, *Pyricularia*, *Pythium*, *Ramularia*, *Rhizoctonia*, *Rhizopus*, *Rhynchosporium*, *Sarocladium*, *Podosphaera* Genus: Sclerotinia, Sclerotium, Septoria, Sphacelotheca, Tapesia, Taphrina, Thievabbussis, Tilletia, Typhula, Uncinula, Urocystis, Uromyces, Ustilago, Venturia, and Verticillium. The plant pathogenic fungi are more preferably selected from the list consisting of: *Alternaria*, *Erysticercus*, *Botrytis*, *Cercospora*, *Clavicipitaceae*, *Colletotrichum*, *Metacarpa*, *Fusarium*, *Gibberellinia*, *Gibberellinia*, *Gibberellinia*, *Helminthospohum*, *Helminthospohum*, *Gibberellinia*, *Gibberellinia*, *Metacarpa*, molds, *Cladosporium*, *Gibberellinia*, *Gibberellinia*, *Gibberellinia*, *Gibberellinia*, *Oomycetes*, *Penicillium*. The genera *Peronospora*, *Cyclocarya*, *Laminaria*, *Stemona*, *Pseudomonas*, *Plasmodium*, *Plasmodium*, *Plasmodium*, *Monocotyle*, *Cyclocarya*, *Pseudomonas*, *Stemona*, *Sclerotium*, *Pyth ... The most preferred selection of the plant pathogenic fungi is from the list consisting of the following genera: Alternaria, Erythrophagus bryonicum, Botrytis, Cercospora, Colletotrichum, Messula, Fusarium, Gibberella, Discospora, Helminthospohum, Helminthospohum, Micrococcus, Messula macrocarpa, molds, oomycetes, Downy mildew, Strains, Stem punctata, Phytophthora, Styloides, Pythium, Pseudomonas, Sclerotium, Sclerotium, Sclerotium, and Nematospermum.

[0179] The plant pathogenic bacteria are preferably from the genera Acidovorax, Agrobacterium, Burkholderia, Clavibacter, Erwinia, Pantoea, Pectobacterium, Phytoplasma, Pseudomonas, Ralstonia, Spiroplasma, Streptomyces, Xanthomonas, or Xylella.

[0180] The plant pathogen virus is preferably a mosaic virus. Additionally and / or alternatively, the plant pathogen virus is preferably selected from the list consisting of: Tobacco mosaic virus, Tomoato spotted wilt virus, Tomato yellow leaf curl virus, Cucumber mosaic virus, Potato virus Y, Cauliflower mosaic virus, African cassava mosaic virus, Plum pox virus, Brome mosaic virus, and Potato virus X.

[0181] The plant pathogenic insects are preferably from the families Plutellidae, Noctuidea, Aphididae, Tenebrionidae, Drosophilidae, Delphacidae, Chrysomelidae, Crambidae, Thripidae, Pentatomidae, Chrysomelidae, Tetranychidae, or Aphrophoridae. More preferably, the plant pathogenic insects belong to the genera *Plutella*, *Spodoptera*, *Myzus*, *Nilaparvata*, *Helicoverpa*, *Diabrotica*, *Chilo*, *Thrips*, *Euschistus*, *Phaedon*, *Tetranichus*, *Sitobion*, *Tribolium*, *Drosophila*, or *Philaenus*. More preferably, the plant pathogenic insects are selected from the list consisting of: *Plutella*, *Spodoptera*, *Myzus*, *Nilaparvata*, *Helicoverpa*, *Diabrotica*, *Chilo*, *Thrips*, *Euschistus*, *Phaedon*, *Tetranichus*, *Sitobion*, *Tribolium*, *Drosophila*, or *Philaenus*.

[0182] In relation to biological stress, a preferred embodiment is that the sialic acid-containing sugar is as disclosed in the section "Sialic Acid-Containing Sugars".

[0183] In a more preferred embodiment, the sialic acid-containing sugar comprises sialic acid linked to a monosaccharide via an α-2,3-bond (preferably, wherein the sialic acid is 9-carbon sialic acid or 8-carbon sialic acid, more preferably 9-carbon sialic acid, more preferably Neu5Ac); preferably, wherein the monosaccharide is selected from galactose, N-acetylglucosamine and sialic acid, more preferably, the monosaccharide is galactose or N-acetylglucosamine, more preferably, the monosaccharide is galactose.

[0184] Preferably, the sialic acid-containing sugar comprises oligosaccharides selected from the list of 3'SL, 3'SLNB, 3'SLNAc, 3'KDO-lactose, 3'KDO-LNB, and 3'KDO-LacNAc, more preferably selected from the list of 3'SL, 3'SLNB, 3'SLAcNAc, and 3'KDO-lactose, and most preferably selected from the list of 3'SL, 3'SLNB, and 3'SLAcNAc; optionally, the oligosaccharides further comprise one or more additional monosaccharides, preferably selected from the list of glucose, galactose, N-acetylglucosamine, N-acetylglucosamine, fucose, and sialic acid, more preferably selected from the list of glucose, galactose, N-acetylglucosamine, fucose, and sialic acid, more preferably selected from the list of galactose, N-acetylglucosamine, fucose, and sialic acid, and most preferably selected from the list of galactose, N-acetylglucosamine, and fucose.

[0185] Additionally and / or alternatively, preferably, the sialic acid-containing sugar comprises lactose, lacto-N-biose (LNB), or N-acetyllactosamine (LacNAc), preferably, the sialic acid-containing sugar comprises lactose or LacNAc, most preferably, the sialic acid-containing sugar comprises lactose; optionally, the sugar further comprises one or more additional monosaccharides, preferably selected from the list consisting of glucose, galactose, N-acetylglucosamine, N-acetylgalactosamine, fucose, and sialic acid, more preferably selected from the list consisting of glucose, galactose, N-acetylglucosamine, fucose, and sialic acid, more preferably selected from the list consisting of galactose, N-acetylglucosamine, fucose, and sialic acid, most preferably selected from the list consisting of galactose, N-acetylglucosamine, and fucose. More preferably, the sialic acid-containing sugar contains lactose, lacto-N-biose (LNB), or N-acetyllactosamine (LacNAc) at its reducing end. Preferably, the sialic acid-containing sugar contains lactose or LacNAc at its reducing end. Most preferably, the sialic acid-containing sugar contains lactose at its reducing end.

[0186] More preferably, the sialylated sugars are selected from the list consisting of 3'-sialyl lactose (3'SL), 3,6-disialial lactose, 3'S-2'FL, 3'S-3-FL, Neu5ac-α-2,6-(Neu5ac-α-2,3-)Gal-β-1,4-Glc, LST a, LST d, DSLNT, DS'LNnT, 3'-sialyl lacto-N-biose (3'SLNB), 3'-sialyl lactosamine (3'SLacNAc), sialyl Lewis x, 3'KDO-lactose, 3'KDO-LNB, and 3'KDO-LacNAc; more preferably, they are selected from the list consisting of 3'-sialyl lactose (3'SL), 3'S-2'FL, 3'S-3-FL, LST a, LST d. A list consisting of 3'-sialyl-N-biose (3'SLNB), 3'-sialyl-lactosamine (3'SLacNAc), sialyl Lewis x, 3'KDO-lactose, 3'KDO-LNB, and 3'KDO-LacNAc; more preferably, a list consisting of 3'-sialyl-lactose (3'SL), 3'S-3-FL, LST a, LST d. A list consisting of 3'-sialyl-N-biose (3'SLNB), 3'-sialyl-lactosamine (3'SLacNAc), sialyl Lewis x, 3'KDO-lactose, 3'KDO-LNB, and 3'KDO-LacNAc; more preferably, a list consisting of 3'-sialyl-lactose (3'SL), LST a, LST d, a list consisting of 3'-sialyl-N-biose (3'SLNB), 3'-sialyl-lactosamine (3'SLacNAc), sialyl Lewis x, 3'KDO-lactose, 3'KDO-LNB, and 3'KDO-LacNAc; more preferably, a list consisting of 3'-sialyl-lactose (3'SL), LST a, LST d, 3'-sialyl-N-biose (3'SLNB), 3'-sialyl-lactosamine (3'SLacNAc), 3'KDO-lactose, 3'KDO-LNB, and 3'KDO-LacNAc; more preferably, a list consisting of 3'-sialyl-lactose (3'SL), LST a, LST d, 3'-sialyl-N-biose (3'SLNB), 3'-sialyl-lactosamine (3'SLacNAc), 3'KDO-lactose, 3'KDO-LNB, and 3'KDO-LacNAc; more preferably, a list consisting of 3'-sialyl-lactose (3'SL), LST a, LST The list consisting of d, 3'-sialyl-N-biose (3'SLNB), 3'-sialyl-lactosamine (3'SLacNAc), and 3'KDO-lactose; more preferably, the list consisting of 3'-sialyl-lactose (3'SL), LST a, LST d, 3'-sialyl-N-biose (3'SLNB), and 3'-sialyl-lactosamine (3'SLacNAc); more preferably, the list consisting of 3'-sialyl-lactose (3'SL), LST a, 3'-sialyl-N-biose (3'SLNB), and 3'-sialyl-lactosamine (3'SLacNAc); most preferably, 3'SL, 3'SLNB, or 3'SLacNAc.

[0187] In a more preferred embodiment, the sialic acid-containing sugar comprises sialic acid linked to a monosaccharide via an α-2,6-bond (preferably, wherein the sialic acid is 9-carbon sialic acid or 8-carbon sialic acid, more preferably 9-carbon sialic acid, more preferably Neu5Ac); preferably, wherein the monosaccharide is selected from galactose, N-acetylglucosamine and sialic acid, more preferably, the monosaccharide is galactose or N-acetylglucosamine, more preferably, the monosaccharide is galactose.

[0188] Preferably, the sialic acid-containing sugar comprises oligosaccharides selected from the list of 6'SL, 6'SLNB, 6'SLAcNAc, 6'KDO-lactose, 6'KDO-LNB, and 6'KDO-LacNAc; more preferably selected from the list of 6'SL, 6'SLNB, 6'SLAcNAc, and 6'KDO-lactose; and most preferably selected from the list of 6'SL, 6'SLNB, and 6'SLAcNAc. Optionally, the oligosaccharides further comprise one or more additional monosaccharides, preferably selected from the list of glucose, galactose, N-acetylglucosamine, N-acetylglucosamine, fucose, and sialic acid; more preferably selected from the list of glucose, galactose, N-acetylglucosamine, fucose, and sialic acid; even more preferably selected from the list of galactose, N-acetylglucosamine, fucose, and sialic acid; and most preferably selected from the list of galactose, N-acetylglucosamine, and fucose.

[0189] Additionally and / or alternatively, preferably, the sialic acid-containing sugar comprises lactose, lacto-N-biose (LNB), or N-acetyllactosamine (LacNAc), preferably, the sialic acid-containing sugar comprises lactose or LacNAc, most preferably, the sialic acid-containing sugar comprises lactose; optionally, the sugar further comprises one or more additional monosaccharides, preferably selected from the list consisting of glucose, galactose, N-acetylglucosamine, N-acetylgalactosamine, fucose, and sialic acid, more preferably selected from the list consisting of glucose, galactose, N-acetylglucosamine, fucose, and sialic acid, more preferably selected from the list consisting of galactose, N-acetylglucosamine, fucose, and sialic acid, most preferably selected from the list consisting of galactose, N-acetylglucosamine, and fucose. More preferably, the sialic acid-containing sugar contains lactose, lacto-N-biose (LNB), or N-acetyllactosamine (LacNAc) at its reducing end. Preferably, the sialic acid-containing sugar contains lactose or LacNAc at its reducing end. Most preferably, the sialic acid-containing sugar contains lactose at its reducing end.

[0190] More preferably, the sialic acid-containing sugar is selected from 6-sialyl-lactose (6'SL), 3,6-disialyl-lactose, 6,6'-disialyl-lactose, 6'S-2'FL, 6'S-3-FL, Neu5Ac-α-2,6-(GlcNAc-β-1,3-)Gal-β-1,4-Glc, Neu5Ac-α-2,6-(Neu5Ac-α-2,3-)Gal-β-1,4-Glc, LST b, LST c. The list consisting of DSLNT, DS'LNT, DSLNnT, DS'LNnT, 6'-sialyl-lact-N-disaccharide (6'SLNB), 6'-sialyl-lactosamine (6'SLacNAc), 6'KDO-lactose, 6'KDO-LNB, and 6'KDO-LacNAc; more preferably selected from the list consisting of 6'-sialyl-lactose (6'SL), 3,6-disialial-lactose, 6'S-2'FL, 6'S-3-FL, Neu5Ac-α-2,6-(GlcNAc-β-1,3-)Gal-β-1,4-Glc, Neu5Ac-α-2,6-(Neu5Ac-α-2,3-)Gal-β-1,4-Glc, LST b. LST c. A list consisting of DSLNT, DS'LNT, DSLNnT, DS'LNnT, 6'-sialyl-lact-N-disaccharide (6'SLNB), 6'-sialyl-lactosamine (6'SLacNAc), 6'KDO-lactose, 6'KDO-LNB, and 6'KDO-LacNAc; more preferably selected from the list consisting of 6'-sialyl-lactose (6'SL), 6'S-2'FL, 6'S-3-FL, Neu5Ac-α-2,6-(GlcNAc-β-1,3-)Gal-β-1,4-Glc, LST b. LST c, DSLNnT, DS'LNT, 6'-sialyl-lactose-N-biose (6'SLNB), 6'-sialyl-lactosamine (6'SLacNAc), 6'KDO-lactose, 6'KDO-LNB, and 6'KDO-LacNAc; more preferably, a list consisting of 6'-sialyl-lactose (6'SL), Neu5Ac-α-2,6-(GlcNAc-β-1,3-)Gal-β-1,4-Glc, LST b, LST c, 6'-sialyl-lactose-N-biose (6'SLNB), 6'-sialyl-lactosamine (6'SLacNAc), 6'KDO-lactose, 6'KDO-LNB, and 6'KDO-LacNAc; more preferably, a list consisting of 6'-sialyl-lactose (6'SL), LST b, LST c. A list consisting of 6'-sialyl-lact-N-biose (6'SLNB), 6'-sialyl-lactosamine (6'SLacNAc), 6'KDO-lactose, 6'KDO-LNB, and 6'KDO-LacNAc;More preferably, the list consisting of 6'-sialyl lactose (6'SL), LST b, LST c, 6'-sialyl lacto-N-biose (6'SLNB), 6'-sialyl lactosamine (6'SLacNAc), and 6'-KDO-lactose is selected; even more preferably, the list consisting of 6'-sialyl lactose (6'SL), LST b, LST c, 6'-sialyl lacto-N-biose (6'SLNB), and 6'-sialyl lactosamine (6'SLacNAc) is selected; even more preferably, the list consisting of 6'-sialyl lactose (6'SL), LST b, and LST c is selected; most preferably, 6'SL or LST c is selected.

[0191] In the case of non-biological stress, the preferred embodiment is that the sialic acid-containing sugar is as disclosed in the section "Sialic Acid-Containing Sugars".

[0192] In relation to abiotic stress, a more preferred embodiment is that the sialic acid-containing sugar comprises sialic acid linked to a monosaccharide via an α-2,3 bond (preferably, wherein the sialic acid is 9-carbon sialic acid or 8-carbon sialic acid, more preferably 9-carbon sialic acid, more preferably Neu5Ac), and wherein the sialic acid-containing sugar is as described herein in relation to biotic stress. However, a more preferred embodiment is that the sialic acid-containing sugar comprises sialic acid linked to a monosaccharide via an α-2,6 bond (preferably, the sialic acid is 9-carbon sialic acid or 8-carbon sialic acid, more preferably 9-carbon sialic acid, more preferably Neu5Ac); preferably, wherein the monosaccharide is selected from galactose, N-acetylglucosamine, and sialic acid (preferably Neu5Ac), more preferably, the monosaccharide is galactose or N-acetylglucosamine, more preferably, the monosaccharide is galactose.

[0193] Preferably, the sialic acid-containing sugar comprises oligosaccharides selected from the list of 6'SL, 6'SLNB, 6'SLAcNAc, 6'KDO-lactose, 6'KDO-LNB, and 6'KDO-LacNAc; more preferably selected from the list of 6'SL, 6'SLNB, 6'SLAcNAc, and 6'KDO-lactose; and most preferably selected from the list of 6'SL, 6'SLNB, and 6'SLAcNAc. Optionally, the oligosaccharides further comprise one or more additional monosaccharides, preferably selected from the list of glucose, galactose, N-acetylglucosamine, N-acetylglucosamine, fucose, and sialic acid; more preferably selected from the list of glucose, galactose, N-acetylglucosamine, fucose, and sialic acid; even more preferably selected from the list of galactose, N-acetylglucosamine, fucose, and sialic acid; and most preferably selected from the list of galactose, N-acetylglucosamine, and fucose.

[0194] Additionally and / or alternatively, preferably, the sialic acid-containing sugar comprises lactose, lacto-N-biose (LNB), or N-acetyllactosamine (LacNAc), preferably, the sialic acid-containing sugar comprises lactose or LacNAc, most preferably, the sialic acid-containing sugar comprises lactose; optionally, the sugar further comprises one or more additional monosaccharides, preferably selected from the list consisting of glucose, galactose, N-acetylglucosamine, N-acetylgalactosamine, fucose, and sialic acid, more preferably selected from the list consisting of glucose, galactose, N-acetylglucosamine, fucose, and sialic acid, more preferably selected from the list consisting of galactose, N-acetylglucosamine, fucose, and sialic acid, most preferably selected from the list consisting of galactose, N-acetylglucosamine, and fucose. More preferably, the sialic acid-containing sugar contains lactose, lacto-N-biose (LNB), or N-acetyllactosamine (LacNAc) at its reducing end. Preferably, the sialic acid-containing sugar contains lactose or LacNAc at its reducing end. Most preferably, the sialic acid-containing sugar contains lactose at its reducing end.

[0195] More preferably, the sialylated sugars are selected from 6'-sialyl lactose (6'SL), 3,6-disialyl lactose, 6,6'-disialyl lactose, 6'S-2'FL, 6'S-3-FL, Neu5Ac-α-2,6-(GlcNAc-β-1,3-)Gal-β-1,4-Glc, Neu5Ac-α-2,6-(Neu5Ac-α-2,3-)Gal-β-1,4-Glc, LST b, LST c. The list consisting of DSLNT, DS'LNT, DSLNnT, DS'LNnT, 6'-sialyl-lact-N-disaccharide (6'SLNB), 6'-sialyl-lactosamine (6'SLacNAc), 6'KDO-lactose, 6'KDO-LNB, and 6'KDO-LacNAc; more preferably selected from the list consisting of 6'-sialyl-lactose (6'SL), 3,6-disialial-lactose, 6'S-2'FL, 6'S-3-FL, Neu5Ac-α-2,6-(GlcNAc-β-1,3-)Gal-β-1,4-Glc, Neu5Ac-α-2,6-(Neu5Ac-α-2,3-)Gal-β-1,4-Glc, LST b. LST c. A list consisting of DSLNT, DS'LNT, DSLNnT, DS'LNnT, 6'-sialyl-lact-N-disaccharide (6'SLNB), 6'-sialyl-lactosamine (6'SLacNAc), 6'KDO-lactose, 6'KDO-LNB, and 6'KDO-LacNAc; more preferably selected from the list consisting of 6'-sialyl-lactose (6'SL), 6'S-2'FL, 6'S-3-FL, Neu5Ac-α-2,6-(GlcNAc-β-1,3-)Gal-β-1,4-Glc, LST b. LST c, DSLNnT, DS'LNT, 6'-sialyl-lactose-N-biose (6'SLNB), 6'-sialyl-lactosamine (6'SLacNAc), 6'KDO-lactose, 6'KDO-LNB, and 6'KDO-LacNAc; more preferably, a list consisting of 6'-sialyl-lactose (6'SL), Neu5Ac-α-2,6-(GlcNAc-β-1,3-)Gal-β-1,4-Glc, LST b, LST c, 6'-sialyl-lactose-N-biose (6'SLNB), 6'-sialyl-lactosamine (6'SLacNAc), 6'KDO-lactose, 6'KDO-LNB, and 6'KDO-LacNAc; more preferably, a list consisting of 6'-sialyl-lactose (6'SL), LST b, LST c. A list consisting of 6'-sialyl-lact-N-biose (6'SLNB), 6'-sialyl-lactosamine (6'SLacNAc), 6'KDO-lactose, 6'KDO-LNB, and 6'KDO-LacNAc;More preferably, the list consisting of 6'-sialyl lactose (6'SL), LST b, LST c, 6'-sialyl lacto-N-biose (6'SLNB), 6'-sialyl lactosamine (6'SLacNAc), and 6'-KDO-lactose is selected; even more preferably, the list consisting of 6'-sialyl lactose (6'SL), LST b, LST c, 6'-sialyl lacto-N-biose (6'SLNB), and 6'-sialyl lactosamine (6'SLacNAc) is selected; even more preferably, the list consisting of 6'-sialyl lactose (6'SL), LST b, and LST c is selected; more preferably, 6'SL or LST c; most preferably, 6'SL.

[0196] As detailed in the "Additional Sugars" section, in the method of the present invention, one or more additional sugars are optionally applied, preferably one or more additional oligosaccharides, more preferably one or more additional lactooligosaccharides, even more preferably one or more additional mammalian lactooligosaccharides, and most preferably one or more additional human lactooligosaccharides. The one or more additional sugars may be sialylated sugars as described in the "Sialic Acid-Containing Sugars" section. Alternatively and additionally, the one or more additional sugars may be sialic acid as described in the "Additional Sugars" section. Alternatively and additionally, the one or more additional sugars may be intermediate sugars as described in the "Additional Sugars" section. Alternatively and additionally, the one or more additional sugars may be non-fucosylated sugars as described in the "Additional Sugars" section. Alternatively and additionally, the one or more additional sugars may be fucosylated sugars as described in the "Additional Sugars" section. Alternatively and additionally, the one or more additional sugars may be monosaccharides as described in the "Additional Sugars" section.

[0197] In relation to abiotic and / or biotic stress, it is particularly preferred that one or more additional sugars are fucosylated sugars containing fucose linked to a monosaccharide via an α-1,3- or α-1,2- bond; preferably, the monosaccharide is selected from glucose, N-acetylglucosamine, and galactose.

[0198] More preferably, the fucosylated sugar comprises an oligosaccharide selected from the list of 2'FL, 3-FL, 2'FLNB, 2'FLacNAc, and 3FLacNAc, preferably selected from the list of 3-FL, 2'FL, and 3FLacNAc, and most preferably 3-FL or 2'FL; optionally, the oligosaccharide further comprises one or more additional monosaccharides, preferably selected from the list of glucose, galactose, N-acetylglucosamine, N-acetylglucosamine, fucose, and sialic acid, more preferably selected from the list of glucose, galactose, N-acetylglucosamine, N-acetylglucosamine, and fucose. Additionally and / or alternatively, preferably, the fucosylated sugar comprises lactose, lacto-N-biose (LNB), or N-acetyllactosamine (LacNAc), preferably, the fucosylated sugar comprises lactose or LacNAc, most preferably, the fucosylated sugar comprises lactose; more preferably, the fucosylated sugar comprises lactose, lacto-N-biose (LNB), or N-acetyllactosamine (LacNAc) at its reducing end, preferably, the fucosylated sugar comprises lactose or LacNAc at its reducing end, most preferably, the fucosylated sugar comprises lactose at its reducing end.

[0199] More preferably, the fucosylated sugar is selected from 2'-fucosyllactose (2'FL), 3-fucosyllactose (3-FL), difucosyllactose (diFL), 2'-fucosyl-N-acetyllactosamine (2'FlacNAc), difucosyl-N-acetyllactosamine (diFLacNAc), 3-fucosyl-N-acetyllactosamine (3FlacNAc), 2'-fucosyllacto-N-biose (2'FLNB), difucosyllacto-N-biose (diFLNB), lacto-N-fucopentose I (LNFP I), blood group A antigen hexasaccharide type 1 (GalNAc-LNFP I), blood group B antigen hexasaccharide type 1 (Gal-LNFP I), lacto-N-fucopentose II (LNFP II), lacto-N-fucopentose III (LNFP III), and lacto-N-fucopentose V (LNFP II). A list consisting of lacto-N-difucohexose I (LNDFH I), lacto-N-difucohexose II (LNDFH II), Lewis b-Lewis x, monofucosyl lacto-N-hexose III (MFLNH III), difucosyl lacto-N-hexose (a) (DFLNH (a)), difucosyl lacto-N-hexose (DFLNH), trifucosyl lacto-N-hexose (TFLNH), lacto-N-neofucopentose I (LNnFP I), lacto-N-neofucopentose V (LNnFP V, LNFP VI) and lacto-N-neodifucohexose (LNnDFH). More preferably, the fucosylated sugars of the present invention are selected from the list consisting of 2'FL, 3-FL, diFL, 2'FlacNAc, diFLacNAc, 3FlacNAc, 2'FLNB, diFLNB, LNFP I, LNFP II, LNFP III, LNFP V, LNDFH I, LNDFH II, LNnFP I, LNnFP V (LNFP VI), and LNnDFH. More preferably, the fucosylated sugars of the present invention are selected from the list consisting of 2'FL, 3-FL, diFL, 2'FlacNAc, diFLacNAc, 3FlacNAc, 2'FLNB, diFLNB, LNFP I, LNFP II, LNFP III, LNFP V, LNnFP I, and LNnFP V (LNFP VI). More preferably, the fucosylated sugars of the present invention are selected from the list consisting of 2'FL, 3-FL, diFL, 2'FlacNAc, diFLacNAc, 3FlacNAc, 2'FLNB, diFLNB, LNFP I, LNFP III, LNFP V, LNnFP I and LNnFP V (LNFPVI).Most preferably, the fucosylated sugars of the present invention are selected from the list consisting of 2'FL, 3-FL, diFL, LNFP I, LNFP III, LNFP V, LNnFP I and LNnFP V (LNFP VI).

[0200] Furthermore, regarding abiotic stress (especially frost), and / or regarding the ability to improve fruit set, and / or regarding the improvement of flower development, and / or regarding the protection of flowers, when: (i) The sialic acid-containing carbohydrates of the present invention, preferably sialic acid-containing carbohydrates, comprising sialic acid linked to a monosaccharide via an α-2,6-bond (preferably, wherein the sialic acid is a nine-carbon sialic acid or an eight-carbon sialic acid, more preferably a nine-carbon sialic acid, more preferably Neu5Ac), as described above in this section; and (ii) Fucosylated sugars comprising fucose linked to monosaccharides via α-1,3- or α-1,2- bonds (preferably α-1,2- bonds); preferably, wherein the monosaccharides are selected from glucose, N-acetylglucosamine, and galactose; When applied to the plant, parts of the plant, seeds of the plant, and / or the intended growth area of ​​the plant, a synergistic protective effect is achieved.

[0201] The sialic acid-containing sugar preferably comprises oligosaccharides selected from the list of 6'SL, 6'SLNB, 6'SLAcNAc, 6'KDO-lactose, 6'KDO-LNB, and 6'KDO-LacNA, more preferably selected from the list of 6'SL, 6'SLNB, 6'SLAcNAc, and 6'KDO-lactose, and most preferably selected from the list of 6'SL, 6'SLNB, and 6'SLAcNAc; optionally, the oligosaccharides further comprise one or more additional monosaccharides, preferably selected from the list of glucose, galactose, N-acetylglucosamine, N-acetylglucosamine, fucose, and sialic acid, more preferably selected from the list of glucose, galactose, N-acetylglucosamine, fucose, and sialic acid, more preferably selected from the list of galactose, N-acetylglucosamine, fucose, and sialic acid, and most preferably selected from the list of galactose, N-acetylglucosamine, and fucose. Additionally and / or alternatively, preferably, the sialic acid-containing sugar comprises lactose, lacto-N-biose (LNB), or N-acetyllactosamine (LacNAc), preferably, the sialic acid-containing sugar comprises lactose or LacNAc, most preferably, the sialic acid-containing sugar comprises lactose; optionally, the sialic acid-containing sugar further comprises one or more additional monosaccharides, preferably selected from the list consisting of glucose, galactose, N-acetylglucosamine, N-acetylgalactosamine, fucose, and sialic acid, more preferably selected from the list consisting of glucose, galactose, N-acetylglucosamine, fucose, and sialic acid, more preferably selected from the list consisting of galactose, N-acetylglucosamine, fucose, and sialic acid, most preferably selected from the list consisting of galactose, N-acetylglucosamine, and fucose. More preferably, the sialic acid-containing sugar contains lactose, lacto-N-biose (LNB), or N-acetyllactosamine (LacNAc) at its reducing end. Preferably, the sialic acid-containing sugar contains lactose or LacNAc at its reducing end. Most preferably, the sialic acid-containing sugar contains lactose at its reducing end. More preferably, the sialic acid-containing sugars are selected from the list consisting of 6'-sialyl-lactose (6'SL), 3,6-disialyl-lactose, 6,6'-disialyl-lactose, 6'S-2'FL, 6'S-3-FL, Neu5Ac-α-2,6-(GlcNAc-β-1,3-)Gal-β-1,4-Glc, Neu5Ac-α-2,6-(Neu5Ac-α-2,3-)Gal-β-1,4-Glc, LST b, LST c, DSLNT, DS'LNT, DSLNnT, DS'LNnT, 6'-sialyl-lact-N-biose (6'SLNB), 6'-sialyl-lactosamine (6'SLacNAc), 6'KDO-lactose, 6'KDO-LNB, and 6'KDO-LacNAc;More preferably, it is selected from 6'-sialyl lactose (6'SL), 3,6-disialyl lactose, 6'S-2'FL, 6'S-3-FL, Neu5Ac-α-2,6-(GlcNAc-β-1,3-)Gal-β-1,4-Glc, Neu5Ac-α-2,6-(Neu5Ac-α-2,3-)Gal-β-1,4-Glc, LST b, LST c. A list consisting of DSLNT, DS'LNT, DSLNnT, DS'LNnT, 6'-sialyl-lact-N-disaccharide (6'SLNB), 6'-sialyl-lactosamine (6'SLacNAc), 6'KDO-lactose, 6'KDO-LNB, and 6'KDO-LacNAc; more preferably selected from the list consisting of 6'-sialyl-lactose (6'SL), 6'S-2'FL, 6'S-3-FL, Neu5Ac-α-2,6-(GlcNAc-β-1,3-)Gal-β-1,4-Glc, LST b. LST c. A list consisting of DSLNnT, DS'LNT, 6'-sialyl-lactose-N-biose (6'SLNB), 6'-sialyl-lactosamine (6'SLacNAc), 6'KDO-lactose, 6'KDO-LNB, and 6'KDO-LacNAc; more preferably, a list consisting of 6'-sialyl-lactose (6'SL), Neu5Ac-α-2,6-(GlcNAc-β-1,3-)Gal-β-1,4-Glc, LST b, LST c. A list consisting of 6'-sialyl-lactose-N-biose (6'SLNB), 6'-sialyl-lactosamine (6'SLacNAc), 6'KDO-lactose, 6'KDO-LNB, and 6'KDO-LacNAc; more preferably, a list consisting of 6'-sialyl-lactose (6'SL), LSTb, LST c, a list consisting of 6'-sialyl-lactose-N-biose (6'SLNB), 6'-sialyl-lactosamine (6'SLacNAc), 6'KDO-lactose, 6'KDO-LNB, and 6'KDO-LacNAc; more preferably, a list consisting of 6'-sialyl-lactose (6'SL), LST b, LSTc, 6'-sialyl-lactose-N-biose (6'SLNB), 6'-sialyl-lactosamine (6'SLacNAc), and 6'KDO-lactose; more preferably, a list consisting of 6'-sialyl-lactose (6'SL), LST b, LST c, 6'-sialyl-lactose-N-biose (6'SLNB), and 6'-sialyl-lactosamine (6'SLacNAc); more preferably, a list consisting of 6'-sialyl-lactose (6'SL), LST b, and LST c; more preferably, 6'SL or LST c; most preferably, 6'SL.

[0202] The fucosylated sugar preferably comprises oligosaccharides selected from the list of 2'FL, 3-FL, 2'FLNB, 2'FLacNAc, and 3FLacNAc, more preferably from the list of 2'FL, 3-FL, 2'FLNB, 2'FLAcNAc, and 3FLacNAc, even more preferably from the list of 3-FL, 2'FL, and 3FLAcNAc, and most preferably 3-FL or 2'FL; optionally, the oligosaccharides further comprise one or more additional monosaccharides, preferably selected from the list of glucose, galactose, N-acetylglucosamine, fucose, and N-acetylglucosamine, more preferably from the list of glucose, galactose, fucose, and N-acetylglucosamine, even more preferably from the list of galactose, N-acetylglucosamine, and fucose. Additionally and / or alternatively, preferably, the fucosylated sugar comprises lactose, lacto-N-biose (LNB), or N-acetyllactosamine (LacNAc), preferably, the fucosylated sugar comprises lactose or LacNAc, most preferably, the fucosylated sugar comprises lactose; optionally, the fucosylated sugar further comprises one or more additional monosaccharides, preferably selected from the list consisting of glucose, galactose, N-acetylglucosamine, fucose, and N-acetylgalactosamine, more preferably selected from the list consisting of glucose, galactose, fucose, and N-acetylglucosamine, and even more preferably selected from the list consisting of galactose, N-acetylglucosamine, and fucose. More preferably, the fucosylated sugar contains lactose, lacto-N-biose (LNB), or N-acetyllactosamine (LacNAc) at its reducing end. Preferably, the fucosylated sugar contains lactose or LacNAc at its reducing end. Most preferably, the fucosylated sugar contains lactose at its reducing end.More preferably, the fucosylated sugar is selected from 2'-fucosyllactose (2'FL), 3-fucosyllactose (3-FL), difucosyllactose (diFL), 2'-fucosyl-N-acetyllactosamine (2'FlacNAc), difucosyl-N-acetyllactosamine (diFLacNAc), 3-fucosyl-N-acetyllactosamine (3FlacNAc), 2'-fucosyllacto-N-biose (2'FLNB), difucosyllacto-N-biose (diFLNB), lacto-N-fucopentose I (LNFP I), blood group A antigen hexasaccharide type 1 (GalNAc-LNFP I), blood group B antigen hexasaccharide type 1 (Gal-LNFP I), lacto-N-fucopentose II (LNFP II), lacto-N-fucopentose III (LNFP III), and lacto-N-fucopentose V (LNFP II). A list consisting of lacto-N-difucohexose I (LNDFH I), lacto-N-difucohexose II (LNDFH II), Lewis b-Lewis x, monofucosyl lacto-N-hexose III (MFLNH III), difucosyl lacto-N-hexose (a) (DFLNH (a)), difucosyl lacto-N-hexose (DFLNH), trifucosyl lacto-N-hexose (TFLNH), lacto-N-neofucopentose I (LNnFP I), lacto-N-neofucopentose V (LNnFP V, LNFP VI) and lacto-N-neodifucohexose (LNnDFH). More preferably, the fucosylated sugars of the present invention are selected from the list consisting of 2'FL, 3-FL, diFL, 2'FlacNAc, diFLacNAc, 3FlacNAc, 2'FLNB, diFLNB, LNFP I, LNFP II, LNFP III, LNFP V, LNDFH I, LNDFH II, LNnFP I, LNnFP V (LNFPVI), and LNnDFH. More preferably, the fucosylated sugars of the present invention are selected from the list consisting of 2'FL, 3-FL, diFL, 2'FlacNAc, diFLacNAc, 3FlacNAc, 2'FLNB, diFLNB, LNFP I, LNFP II, LNFP III, LNFPV, LNnFP I, and LNnFP V (LNFPVI). More preferably, the fucosylated sugars of the present invention are selected from the list consisting of 2'FL, 3-FL, diFL, 2'FlacNAc, diFLacNAc, 3FlacNAc, 2'FLNB, diFLNB, LNFP I, LNFP III, LNFP V, LNnFP I and LNnFP V (LNFP VI).Most preferably, the fucosylated sugars of the present invention are selected from the list consisting of 2'FL, 3-FL, diFL, LNFP I, LNFP III, LNFP V, LNnFP I and LNnFP V (LNFP VI).

[0203] In another preferred embodiment, an effective amount of the sialic acid-containing sugar is applied to the plant, parts of the plant, seeds of the plant, and / or the intended growth area of ​​the plant. With respect to biotic stress, the term "effective amount" refers to the amount required to protect the plant against (preferably control), prevent, or treat the biotic stress (as described herein). If the biotic stress is a fungus or a fungal disease, the effective amount is a fungicide-effective amount, i.e., a relative amount of the sugar capable of effectively inhibiting or controlling the fungal growth rate, increasing fungal mortality, or eradicating the fungus. With respect to abiotic stress, the term "effective amount" refers to the amount required to protect the plant against (preferably control), prevent, or treat the abiotic stress (as described herein). As will be understood by those skilled in the art, the effective amount will vary depending on factors such as the (abiotic) stress to be controlled, the plant species or variety to be treated, climatic conditions, the growth stage of the plant, and the application site (e.g., leaves, roots, or seeds). Those skilled in the art can readily determine the appropriate effective amount in any specific situation (e.g., through systematic field trials, which is within the capabilities of those skilled in the art). In the invention concerning the application of at least one additional sugar to the plant, parts of the plant, seeds of the plant, and / or the intended growth area of ​​the plant in a method for protecting plants against abiotic and / or biotic stresses, it is particularly preferred that each sialic acid-containing sugar and each additional sugar (preferably one or more of the additional sugars being fucosylated sugars) are applied in a synergistic amount. As will be understood by those skilled in the art, a “synergistic amount” of sugar refers to the amount of sugar capable of producing a synergistic effect. For the purposes of this invention, the synergistic effect refers to an improvement in plant protection against abiotic and / or biotic stresses, preferably an improvement in tolerance, that is stronger than the effect observed when the sugars are applied alone.

[0204] In additional and / or preferred embodiments, the sialic acid-containing sugar is applied to the plant in a phytotoxic amount. If one or more additional sugars are applied in the method of the invention, it is preferred to apply any (preferably all) of the additional sugars in a phytotoxic amount. For clarity, the term "phytotoxic" applies to the treated plant, meaning that the applied one or more sugars are non-toxic to the treated plant (or at least, according to the art, their toxicity level is acceptable).

[0205] In a more preferred embodiment, the amount of the sialic acid-containing sugars and (if present) any (preferably all) additional sugars is as described in the sections “Sialic Acid-Containing Sugars” and “Additional Sugars”.

[0206] Use In a second aspect, the present invention provides the use of a sialic acid-containing sugar with a degree of polymerization (DP) of at least 2 as a biostimulant for plant growth and / or plant development. Preferably, the present invention provides the use of a composition as a biostimulant for plant growth and / or plant development, wherein the composition comprises a sialic acid-containing sugar with a degree of polymerization (DP) of at least 2, optionally one or more additional sugars, preferably wherein the additional sugars are as described in the "Additional Sugars" section, more preferably wherein the additional sugars are as described in the "Promoting Growth and / or Development" section.

[0207] In a particularly preferred embodiment, the present invention provides the use of a sialic acid-containing sugar with a degree of polymerization (DP) of at least 2 as a flower development biostimulant. More preferably, the present invention provides the use of a composition as a flower development biostimulant, wherein the composition comprises a sialic acid-containing sugar with a degree of polymerization (DP) of at least 2, optionally one or more additional sugars, preferably wherein the additional sugars are as described in the "Additional Sugars" section, more preferably wherein the additional sugars are as described in the "Promoting Growth and / or Development" section.

[0208] For the purposes of this invention, the terms "sialic acid-containing sugars", "plants", "compositions", "added sugars", "plant growth" and "plant development" used in the second aspect and claims of this invention are as described in the first aspect of this invention.

[0209] In a third aspect, the present invention provides the use of a sialic acid-containing sugar with a degree of polymerization (DP) of at least 2 as a plant protectant. Preferably, the present invention provides the use of a composition as a plant protectant, wherein the composition comprises a sialic acid-containing sugar with a degree of polymerization (DP) of at least 2, optionally one or more additional sugars, preferably wherein the additional sugars are as described in the "Additional Sugars" section, more preferably wherein the additional sugars are as described in the "Abiotic Stress and / or Biological Stress" section.

[0210] In a particularly preferred embodiment, the present invention provides the use of a sialic acid-containing sugar with a degree of polymerization (DP) of at least 2 as a flower protectant. More preferably, the present invention provides the use of a composition as a flower protectant, wherein the composition comprises a sialic acid-containing sugar with a degree of polymerization (DP) of at least 2, optionally one or more additional sugars, preferably wherein the additional sugars are as described in the "Additional Sugars" section, more preferably wherein the additional sugars are as described in the "Abiotic Stress and / or Biological Stress" section.

[0211] For the purposes of this invention, the terms "sialic acid-containing sugars", "plants", "compositions", "added sugars" and "protection" used in the third aspect and claims of this invention are as described in the first aspect of this invention.

[0212] Specific embodiments The present invention preferably relates to the following specific embodiments: 1. A method of treating a plant, wherein the method includes the step of applying a sialic acid-containing sugar to the plant, a portion of the plant, a seed of the plant, and / or a intended growth area of ​​the plant, wherein the degree of polymerization (DP) of the sialic acid-containing sugar is at least 2.

[0213] 2. The method according to embodiment 1, wherein the sialic acid is 9-carbon sialic acid or 8-carbon sialic acid, preferably 9-carbon sialic acid.

[0214] 3. According to the method of embodiment 2, the nine-carbon sialic acid is selected from the list consisting of Neu5Ac; Neu4Ac; Neu4,5Ac2; Neu5,7Ac2; Neu5,8Ac2; Neu5,9Ac2; Neu4,5,9Ac3; Neu5,7,9Ac3; Neu5,8,9Ac3; Neu4,5,7,9Ac4; Neu5,7,8,9Ac4; Neu4,5,7,8,9Ac5; and Neu5Gc, preferably, the nine-carbon sialic acid is N-acetylneuraminic acid (Neu5Ac).

[0215] 4. The method according to embodiment 2, wherein the octacarbon sialic acid is ketodeoxyoctanoic acid (KDO).

[0216] 5. The method according to any one of embodiments 1 to 4, wherein the sialic acid is linked to the monosaccharide by an α-2,3-, α-2,6- or α-2,8- bond, preferably α-2,3- or α-2,6-, more preferably α-2,6-.

[0217] 6. The method according to embodiment 5, wherein the monosaccharide is selected from the list consisting of galactose, N-acetylglucosamine and sialic acid, preferably, the monosaccharide is galactose or N-acetylglucosamine, more preferably, the monosaccharide is galactose.

[0218] 7. According to any one of embodiments 1 to 6, the sialic acid-containing sugar is a disaccharide or oligosaccharide, preferably an oligosaccharide.

[0219] 8. The method according to any one of embodiments 1 to 7, wherein the sialic acid-containing sugar comprises oligosaccharides selected from a list consisting of 3'SL, 6'SL, 3'SLNB, 6'SLNB, 3'SLacNAc, 6'SLacNAc, 3'KDO-lactose, 6'KDO-lactose, 3'KDO-LNB, 6'KDO-LNB, 3'KDO-LacNAc, and 6'KDO-LacNAc, preferably selected from 6'SL, 6'SLNB, 6'SLacNAc, 6'KDO-lactose, 6'KDO- The list consists of LNB and 6'KDO-LacNAc; optionally, the oligosaccharide further comprises one or more additional monosaccharides, the monosaccharides preferably being selected from the list consisting of free glucose, galactose, N-acetylglucosamine, N-acetylglucosamine, fucose and sialic acid, more preferably the list consisting of free glucose, galactose, N-acetylglucosamine, fucose and sialic acid, even more preferably the list consisting of free galactose, N-acetylglucosamine, fucose and sialic acid, and most preferably the list consisting of free galactose, N-acetylglucosamine and fucose.

[0220] 9. The method according to any one of embodiments 1 to 8, wherein the sialic acid-containing sugar comprises lactose, lacto-N-biose (LNB) or N-acetyllactosamine (LacNAc), preferably, the sialic acid-containing sugar comprises lactose or LacNAc, more preferably, the sialic acid-containing sugar comprises lactose.

[0221] 10. The method according to any one of embodiments 1 to 9, wherein the sialic acid-containing sugar contains lactose, lacto-N-biose (LNB) or N-acetyllactosamine (LacNAc) at its reducing end, preferably, the sialic acid-containing sugar contains lactose or LacNAc at its reducing end, more preferably, the sialic acid-containing sugar contains lactose at its reducing end.

[0222] 11. The method according to any one of embodiments 1 to 10, wherein the sialic acid-containing sugar is selected from 3'-sialyl lactose (3'SL), 6'-sialyl lactose (6'SL), 3,6-disialyl lactose, 6,6'-disialyl lactose, 8,3-disialyl lactose, 3'S-2'FL, 6'S-2'FL, 3'S-3-FL, 6'S-3-FL, Neu5Ac-α-2,6-(GlcNAc-β-1,3-)Gal-β-1,4-Glc, Neu5Ac-α-2,6-(Neu5Ac-α-2,3-)Gal-β-1,4-Glc, LST a, LST b, LST c, LST d. A list consisting of bis(sialo-lact-N-tetrasaccharide) (DSLNT), bis(sialo-lact-N-tetrasaccharide) analog (DS'LNT), bis(sialo-lact-N-neo-tetrasaccharide) (DSLNnT), bis(sialo-lact-N-neo-tetrasaccharide) analog (DS'LNnT), 3'-sialo-lact-N-biose (3'SLNB), 6'-sialo-lact-N-biose (6'SLNB), sialic acid Lewis a, 3'-sialo-lactosamine (3'SLacNAc), 6'-sialo-lactosamine (6'SLacNAc), sialic acid Lewis x, 3'KDO-lactose, 6'KDO-lactose, 3'KDO-LNB, 6'KDO-LNB, 3'KDO-LacNAc and 6'KDO-LacNAc; optionally, said sialic acid-containing sugars further comprise fucose.

[0223] 12. The method according to any one of embodiments 1 to 11, wherein the application step is seed application, root application, air application or soil application, preferably seed application or air application.

[0224] 13. The method according to any one of embodiments 1 to 12, wherein the application step includes one or more selected from watering, spraying (including ultra-low volume spraying), irrigation, atomization, spraying, dusting, foaming application, spreading, coating, drenching, drip irrigation and injection.

[0225] 14. The method according to any one of embodiments 1 to 13, wherein the plant is an arable crop, a fruiting plant or a vegetable.

[0226] 15. The method according to any one of embodiments 1 to 14, wherein the plant is under physiological conditions, abiotic stress or biotic stress.

[0227] 16. The method according to any one of embodiments 1 to 15, wherein the sialic acid-containing sugar is part of the composition.

[0228] 17. The method according to any one of embodiments 1 to 16, wherein the method is for promoting the growth and / or development of a plant or a part of a plant.

[0229] 18. The method according to embodiment 17, wherein the growth and / or development refers to one or more of improving plant yield, improving fruiting ability, improving flower development, and improving toughness.

[0230] 19. The method according to any one of embodiments 1 to 16, wherein the method is for protecting a plant or parts of a plant against abiotic and / or biotic stresses.

[0231] 20. The method according to embodiment 19, wherein the abiotic stress is selected from a list consisting of frost, drought, osmotic stress (preferably salinity), humidity (preferably flooding), heat stress, light stress (preferably ultraviolet stress), and mechanical stress; preferably selected from a list consisting of frost, drought, osmotic stress (preferably salinity), humidity (preferably flooding), heat stress, and light stress (preferably ultraviolet stress); more preferably selected from a list consisting of frost, drought, osmotic stress (preferably salinity), humidity (preferably flooding), and light stress (preferably ultraviolet stress); even more preferably selected from a list consisting of frost, drought, osmotic stress (preferably salinity), and humidity (preferably flooding); and most preferably selected from a list consisting of frost, drought, and humidity (preferably flooding).

[0232] 21. The method according to embodiment 19 or 20, wherein the biological stress includes plant pathogens or diseases caused by said plant pathogens.

[0233] 22. The method according to embodiment 21, wherein the plant pathogen is selected from a list consisting of fungi, bacteria, viruses, nematodes, mollusks and insects.

[0234] 23. The method according to embodiment 21 or 22, wherein the plant pathogen is a fungus.

[0235] 24. The method according to any one of embodiments 1 to 23, wherein one or more additional sugars are applied to the plant, a portion of the plant, the seeds of the plant, and / or the intended growth area of ​​the plant.

[0236] 25. The method according to any one of embodiments 1 to 24, wherein the method further includes the step of applying one or more additional sugars.

[0237] 26. The method according to any one of embodiments 1 to 25, wherein the method further comprises the step of applying a non-fucosylated sugar.

[0238] 27. The method according to embodiment 26, wherein the unfucosylated sugar comprises a sugar selected from the list consisting of lactose, LNB, LacNAc, LNT-II, LNT, and LNnT; preferably selected from the list consisting of LNT-II, LNT, and LNnT; optionally, wherein the sugar further comprises one or more additional monosaccharides, the monosaccharides preferably selected from the list consisting of glucose, galactose, N-acetylglucosamine, and N-acetylglucosamine, more preferably selected from the list consisting of glucose, galactose, and N-acetylglucosamine, and even more preferably selected from galactose and N-acetylglucosamine.

[0239] 28. The method according to embodiment 26 or 27, wherein the non-fucosylated sugar comprises lactose, lacto-N-biose (LNB) or N-acetyllactosamine (LacNAc), preferably, the non-fucosylated sugar comprises lactose or LacNAc, and most preferably, the non-fucosylated sugar comprises lactose.

[0240] 29. The method according to any one of embodiments 26 to 28, wherein the non-fucosylated sugar comprises lactose, lacto-N-biose (LNB) or N-acetyllactosamine (LacNAc) at its reducing end, preferably, the non-fucosylated sugar comprises lactose or LacNAc at its reducing end, and most preferably, the non-fucosylated sugar comprises lactose at its reducing end.

[0241] 30. The method according to any one of embodiments 26 to 29, wherein the non-fucosylated sugar is selected from lactose, lacto-N-trisaccharide II (LN3, LNT-II), lacto-N-neotetrasaccharide (LNnT), lacto-N-tetrasaccharide (LNT), para-lacto-N-neopentose, para-lacto-N-pentasaccharide, lacto-N-neopentose, para-lacto-N-neopentose, lacto-N-hexasaccharide, para-lacto-N-neopentose, lacto-N-hexasaccharide, para-lacto-N-hexasaccharide, β-(1,3)galactosyl-para-lacto-N-neopentose, β-(1,4)galactosyl-para-lacto-N-pentasaccharide, Ga l-a1,4-Gal-b1,4-Glc (Gal-a1,4-lactose), β3'-galactosyllactose, β6'-galactosyllactose, Gal-a1,4-Gal-a1,4-Gal-b1,4-Glc, Gal-a1,4-Gal-a1,4-Gal-a1,4-Gal-b1,4-Glc, Gal-b1,3-Galb1,3-Gal-b1,4-Glc, Gal-b1,3-Gal-b1,3-Galb1,3-G al-b1,4-Glc,Gal-b1,3-Gal-b1,3-Gal-b1,3-Galb1,3-Gal-b1,4-Glc,Gal-b1,3-Gal-b1,3-Gal-b1,3-Gal- b1,3-Galb1,3-Gal-b1,4-Glc,GalNAc-b1,3-Gal-b1,4-Glc (GalNAc-b1,3-lactose),Gal-b1,3-GalNAc-b1,3-lactose,G alNAc-b1,3-Gal-a1,4-Gal-b1,4-Glc (globul-N-tetrasaccharide), Gal-b1,3-GalNAc-b1,3-Gal-a1,4-Gal-b1,4-Glc, GalNAc- b1,3-LNT, Gal-b1,3-GalNAc-b1,3-LNT, novo-LNT (GlcNAc-b1,6-[Gal-b1,3]-Gal-b1,4-Glc), Gal-novo-LNP I (Gal-b1,4-GlcNAc-b1,6-[Gal-b1,3-Gal-b1,3]-Gal-b1,4-Glc), Gal-novo-LNP II (Gal-b1,4-GlcNAc-b1,6-[Gal-b1,3]-Gal-b1,3-Gal-b1,4-Glc), Gal-novo-LNP III (Gal-b1,3-Gal-b1,4-GlcNAc-b1,6-[Gal-b1,3]-Gal-b1,4-Glc), novo-LNO, GalNAc-b1,3-LNnT, Gal-b1,3-GalNAc-b1,3-LNnT, LNH, LNnH, iso-LNO, novo-LNO, novo-LNnO, LND, iso-LND, GalNAc-a1,3-Gal-b1,4-Glc, novo-LNP A list consisting of I, iso-LNT, DGalLNnH, galili pentasaccharide, lact-N-heptaose, lact-N-neoheptaose, para-lact-N-neoheptaose, para-lact-N-heptaose, lact-N-octaose (LNO), lact-N-neooctaose, iso-lact-N-octaose, para-lact-N-octaose, iso-lact-N-neooctaose, novo-lact-N-neooctaose, para-lact-N-neooctaose, iso-lact-N-nonaose, novo-lact-N-nonaose, lact-N-nonaose, lact-N-decansaccharide, iso-lact-N-decansaccharide, novo-lact-N-decansaccharide, lact-N-neodecasac, iso-lact-N-decansaccharide, novo-lact-N-decansaccharide, lact-N-neodecasac, LNB, LacNAc, diLacNAc, and poly-LacNAc.

[0242] 31. The method according to any one of embodiments 1 to 30, wherein the method further includes the step of applying fucosylated sugars.

[0243] 32. The method according to embodiment 31, wherein the fucoidylated sugar comprises an oligosaccharide selected from the list of 2'FL, 3-FL, 2'FLNB, 4FLNB, 2'FLacNAc and 3FLacNAc, preferably selected from the list of 2'FL, 3-FL, 2'FLNB, 2'FLAcNAc and 3FLacNAc, more preferably selected from the list of 3-FL, 2'FL and 3FLAcNAc, and most preferably 3-FL or 2'FL; optionally, wherein the oligosaccharide further comprises one or more additional monosaccharides, preferably selected from the list of glucose, galactose, N-acetylglucosamine, N-acetylglucosamine, fucose and sialic acid, more preferably selected from the list of glucose, galactose, N-acetylglucosamine, N-acetylglucosamine and fucose.

[0244] 33. The method according to embodiment 31 or 32, wherein the fucoidylated sugar comprises lactose, lacto-N-biose (LNB) or N-acetyllactosamine (LacNAc), preferably, the fucoidylated sugar comprises lactose or LacNAc, more preferably, the fucoidylated sugar comprises lactose.

[0245] 34. The method according to any one of embodiments 31 to 33, wherein the fucosylated sugar comprises lactose, lacto-N-biose (LNB) or N-acetyllactosamine (LacNAc) at its reducing end, preferably, the fucosylated sugar comprises lactose or LacNAc at its reducing end, more preferably, the fucosylated sugar comprises lactose at its reducing end.

[0246] 35. The method according to any one of embodiments 31 to 34, wherein the fucosylated sugar is selected from 2'-fucosylated lactose (2'FL), 3-fucosylated lactose (3-FL), difucosylated lactose (diFL), 2'-fucosylated-N-acetyllactosamine (2'FlacNAc), difucosylated-N-acetyllactosamine (diFLacNAc), 3-fucosylated-N-acetyllactosamine (3FlacNAc), 2'-fucosylated-N-biose (2'FLNB), 4-fucosylated-N-biose (4FLNB), difucosylated-N-biose (diFLNB), lacto-N-fucopentose I (LNFP I), blood group A antigen hexasaccharide type 1 (GalNAc-LNFPI) and blood group B antigen hexasaccharide type 1 (Gal-LNFP I), lacto-N-fucopentose II (LNFP II), Lacto-N-fucopentose III (LNFP III), Lacto-N-fucopentose V (LNFP V), Lacto-N-difucohexasose I (LNDFH I), Lacto-N-difucohexasose II (LNDFH II), Lewis b-Lewis x, Monofucosyl lacto-N-hexasose III (MFLNH III), Difucosyl lacto-N-hexasose (a) (DFLNH (a)), Difucosyl lacto-N-hexasose (DFLNH), Trifucosyl lacto-N-hexasose (TFLNH), Lacto-N-neofucopentose I (LNnFP I), Lacto-N-neofucopentose V (LNnFP V, LNFP The list consisting of LNFP I, LNFP II, LNFP III, LNFP V, LNDFH I, LNDFH II, LNnFP I, LNnFP V (LNFP VI) and LNnDFH is preferred; the list consisting of LNFP I, LNFP II, LNFP III, LNFP V, LNDFH I, LNDFH II, LNnFP I, LNnFP V (LNFP VI) and LNnDFH is preferred; the list consisting of LNFP I, LNFP II, LNFP III, LNFP V, LNnFP I and LNnFP V (LNFP VI) is more preferred. A list consisting of VI); more preferably a list consisting of 2'FL, 3-FL, diFL, 2'FlacNAc, diFLacNAc, 3FlacNAc, 2'FLNB, diFLNB, LNFP I, LNFP III, LNFP V, LNnFP I and LNnFP V (LNFPVI);Most preferably, the fucosylated sugars are selected from the list consisting of 2'FL, 3-FL, diFL, LNFP I, LNFPIII, LNFP V, LNnFP I, and LNnFP V (LNFP VI).

[0247] 36. The method according to any one of embodiments 1 to 35, wherein the method further comprises the step of applying a fucosylated sugar, said fucosylated sugar comprising fucose linked to a monosaccharide via an α-1,3-bond.

[0248] 37. The method according to embodiment 36, wherein the fucosylated sugar is selected from 3-fucosyllactose (3-FL), difucosyllactose (diFL), difucosyl-N-acetyllactosamine (diFLacNAc), 3-fucosyl-N-acetyllactosamine (3FlacNAc), lacto-N-fucopentose III (LNFP III), lacto-N-fucopentose V (LNFP V), lacto-N-difucohexasose II (LNDFH II), Lewis b-Lewis x, monofucosyl lacto-N-hexasose III (MFLNH III), difucosyl lacto-N-hexasose (a) (DFLNH (a)), difucosyl lacto-N-hexasose (DFLNH), trifucosyl lacto-N-hexasose (TFLNH), lacto-N-neofucopentose V (LNnFP V, LNFP The list consists of LNFP VI and LN-N-neo-difucohexasaccharide (LNnDFH); preferably, it consists of the list consisting of 3-FL, diFL, diFLacNAc, 3FlacNAc, LNFP III, LNFP V, LNDFH II, LNnFP V (LNFP VI) and LNnDFH; more preferably, it consists of the list consisting of 3-FL, diFL, diFLacNAc, 3FlacNAc, LNFP III, LNFP V and LNnFP V (LNFP VI); most preferably, it consists of the list consisting of 3-FL, diFL, diFLacNAc, 3FlacNAc, LNFP V and LNnFP V (LNFP VI); most preferably, the fucosylated sugars are selected from the list consisting of 3-FL, 3FlacNAc, LNFP V and LNnFP V (LNFP VI).

[0249] 38. The method according to any one of embodiments 1 to 37, wherein the method further comprises the step of applying a fucosylated sugar, said fucosylated sugar comprising fucose linked to a monosaccharide via an α-1,2-bond.

[0250] 39. The method according to embodiment 38, wherein the fucosylated sugar is selected from 2'-fucosylated lactose (2'FL), difucosylated lactose (diFL), 2'-fucosylated-N-acetyllactosamine (2'FlacNAc), difucosylated-N-acetyllactosamine (diFLacNAc), 2'-fucosylated-N-biose (2'FLNB), difucosylated-N-biose (diFLNB), lacto-N-fucopentose I (LNFP I), blood group A antigen hexasaccharide type 1 (GalNAc-LNFP I), blood group B antigen hexasaccharide type 1 (Gal-LNFP I), lacto-N-difucohexasaccharide I (LNDFH I), Lewis b-Lewis x, difucosylated-N-hexasaccharide (a) (DFLNH (a) A list consisting of trifucosylated lact-N-hexasaccharide (TFLNH) and lact-N-neofofucopentose I (LNnFP I); preferably selected from a list consisting of 2'FL, diFL, 2'FlacNAc, diFLacNAc, 2'FLNB, diFLNB, LNFP I, LNDFH I and LNnFP I; more preferably selected from a list consisting of 2'FL, diFL, 2'FlacNAc, diFLacNAc, 2'FLNB, diFLNB, LNFP I and LNnFP I; most preferably, the fucosylated sugars are selected from a list consisting of 2'FL, diFL, LNFP I and LNnFP I.

[0251] 40. The method according to any one of embodiments 36 to 39, wherein the monosaccharide is selected from glucose, N-acetylglucosamine, and galactose.

[0252] 41. Use of a sialic acid-containing sugar as a biostimulant for plant growth and / or plant development, wherein the degree of polymerization (DP) of the sialic acid-containing sugar is at least 2.

[0253] 42. Use of a sialic acid-containing sugar as a plant protectant, wherein the degree of polymerization (DP) of the sialic acid-containing sugar is at least 2.

[0254] The present invention more preferably relates to the following specific embodiments: 1. A plant treatment method, wherein the method includes the step of applying a sialic acid-containing sugar to the plant, a portion of the plant, a seed of the plant, and / or a desired growth area of ​​the plant, wherein the degree of polymerization (DP) of the sialic acid-containing sugar is at least 2, and wherein the sialic acid-containing sugar comprises sialic acid linked to a monosaccharide via an α-2,3-, α-2,6-, or α-2,8- bond, wherein the monosaccharide is selected from galactose, N-acetylglucosamine, and sialic acid.

[0255] 2. The method according to embodiment 1, wherein the sialic acid is 9-carbon sialic acid or 8-carbon sialic acid, preferably 9-carbon sialic acid.

[0256] 3. The method according to embodiment 2, wherein the nine-carbon sialic acid is selected from the list consisting of N-acetylneuraminic acid (Neu5Ac), Neu4Ac, Neu4,5Ac2, Neu5,7Ac2, Neu5,8Ac2, Neu5,9Ac2, Neu4,5,9Ac3, Neu5,7,9Ac3, Neu5,8,9Ac3, Neu4,5,7,9Ac4, Neu5,7,8,9Ac4, Neu4,5,7,8,9Ac5, and Neu5Gc, preferably, wherein the nine-carbon sialic acid is N-acetylneuraminic acid (Neu5Ac).

[0257] 4. The method according to embodiment 2, wherein the octacarbon sialic acid is ketodeoxyoctanoic acid (KDO).

[0258] 5. The method according to any one of embodiments 1 to 4, wherein the sialic acid-containing sugar includes lactose, lacto-N-biose (LNB), or N-acetyllactosamine (LacNAc).

[0259] 6. The method according to any one of embodiments 1 to 5, wherein the sialic acid-containing sugar comprises an oligosaccharide selected from the list consisting of 3'SL, 6'SL, 3'SLNB, 6'SLNB, 3'SLacNAc, 6'SLacNAc, 3'KDO-lactose, 6'KDO-lactose, 3'KDO-LNB, 6'KDO-LNB, 3'KDO-LacNAc, and 6'KDO-LacNAc; optionally, wherein the oligosaccharide further comprises one or more additional monosaccharides, the monosaccharides preferably selected from glucose, galactose, N-acetylglucosamine, N-acetylglucosamine, fucose, and sialic acid.

[0260] 7. The method according to any one of embodiments 1 to 6, wherein the sialic acid-containing sugar is selected from 3'-sialyl lactose (3'SL), 6'-sialyl lactose (6'SL), 3,6-disialyl lactose, 6,6'-disialyl lactose, 8,3-disialyl lactose, 3'S-2'FL, 6'S-2'FL, 3'S-3-FL, 6'S-3-FL, Neu5Ac-α-2,6-(GlcNAc-β-1,3-)Gal-β-1,4-Glc, Neu5Ac-α-2,6-(Neu5Ac-α-2,3-)Gal-β-1,4-Glc, LST a, LST b, LST c, a list consisting of LSTd, bis(s)-sialolact-N-tetrasaccharide (DSLNT), bis(s)-sialolact-N-tetrasaccharide analog (DS'LNT), bis(s)-sialolact-N-neotetrasaccharide (DSLNnT), bis(s)-sialolact-N-neotetrasaccharide analog (DS'LNnT), 3'-sialolact-N-biose (3'SLNB), 6'-sialolact-N-biose (6'SLNB), sialic acid Lewis a, 3'-sialolactosamine (3'SLacNAc), 6'-sialolactosamine (6'SLacNAc), sialic acid Lewis x, 3'KDO-lactose, 6'KDO-lactose, 3'KDO-LNB, 6'KDO-LNB, 3'KDO-LacNAc and 6'KDO-LacNAc; optionally, said sialic acid-containing sugars further comprise fucose.

[0261] 8. The method according to any one of embodiments 1 to 7, wherein the application step is seed application, root application, air application, or soil application.

[0262] 9. The method according to any one of embodiments 1 to 8, wherein the application step is seed application or aerial application.

[0263] 10. The method according to any one of embodiments 1 to 9, wherein the application step comprises one or more selected from watering, spraying (including ultra-low volume spraying), irrigation, atomization, spraying, dusting, foaming, spreading, coating, immersion, drip irrigation and injection.

[0264] 11. The method according to any one of embodiments 1 to 10, wherein the application step includes coating, preferably by spraying.

[0265] 12. The method according to any one of embodiments 1 to 10, wherein the sialic acid-containing sugar is part of the composition.

[0266] 13. The method according to any one of embodiments 1 to 12, wherein the method is for promoting the growth and / or development of a plant or a part of a plant.

[0267] 14. The method according to embodiment 13, wherein the growth and / or development refers to one or more of improving plant yield, improving fruiting ability, improving flower development, and improving toughness.

[0268] 15. The method according to any one of embodiments 1 to 12, wherein the method is for protecting a plant or parts of a plant against abiotic and / or biotic stresses.

[0269] 16. The method according to any one of embodiments 1 to 12, wherein the method is for protecting a plant or a part of a plant against abiotic stresses selected from a list consisting of frost, drought, osmotic stress (preferably salt), humidity (preferably flooding), heat stress, light stress (preferably ultraviolet stress), and mechanical stress.

[0270] 17. The method according to any one of embodiments 1 to 12, wherein the method is used to protect a plant or a part of a plant against biotic stress.

[0271] 18. The method according to embodiment 15 or 17, wherein the biological stress includes plant pathogens or diseases caused by said plant pathogens.

[0272] 19. The method according to any one of embodiments 1 to 17, wherein the method further comprises the step of applying one or more additional sugars to the plant, a portion of the plant, the seeds of the plant, and / or the intended growth area of ​​the plant.

[0273] 20. The method according to embodiment 19, wherein the method comprises the step of applying (i) a fucosylated sugar and / or (ii) a non-fucosylated sugar and / or (iii) a monosaccharide and / or (iv) a synthetic intermediate of the sialic acid-containing sugar.

[0274] 21. The method according to embodiment 19 or 20, wherein the method includes the step of applying a fucosylated sugar, the fucosylated sugar comprising fucose linked to a monosaccharide via an α-1,3-bond.

[0275] 22. The method according to any one of embodiments 19 to 21, wherein the method includes the step of applying a fucosylated sugar, the fucosylated sugar comprising fucose linked to a monosaccharide via an α-1,2-bond.

[0276] 23. Use of a sialic acid-containing sugar as a biostimulant for plant growth and / or plant development, wherein the degree of polymerization (DP) of the sialic acid-containing sugar is at least 2, and wherein the sialic acid-containing sugar comprises sialic acid linked to a monosaccharide via an α-2,3-, α-2,6-, or α-2,8- bond, wherein the monosaccharide is selected from galactose, N-acetylglucosamine, and sialic acid.

[0277] 24. Use of a sialic acid-containing sugar as a plant protectant, wherein the degree of polymerization (DP) of the sialic acid-containing sugar is at least 2, and wherein the sialic acid-containing sugar comprises sialic acid linked to a monosaccharide via an α-2,3-, α-2,6-, or α-2,8- bond, wherein the monosaccharide is selected from galactose, N-acetylglucosamine, and sialic acid.

[0278] Definitions The terms used in this specification to describe the invention and its various embodiments should be understood not only in their ordinary sense, but also, through the specific definitions herein, to include structures, materials, or behaviors that extend beyond their ordinary meaning. Therefore, if an element can be understood to have more than one meaning in the context of this specification, its use in the claims must be understood to cover all possible meanings supported by this specification and the term itself.

[0279] The various aspects and embodiments of the invention disclosed herein should be understood not only in the order and context specifically described herein, but also in any order and any combination thereof. Unless otherwise stated, each embodiment identified herein can be combined together. All publications, patents, and patent applications referenced in this specification are incorporated herein by reference in their entirety, with the same effect as if each individual publication, patent, or patent application were expressly indicated to be incorporated herein by reference in its entirety. Unless otherwise expressly stated, all singular terms are to be construed as including the plural form, and vice versa. Unless otherwise defined, all technical and scientific terms used herein generally have the meaning commonly understood by one of ordinary skill in the art to which this invention pertains. Generally, the nomenclature used herein and the laboratory procedures described herein for cell culture, molecular genetics, organic chemistry, nucleic acid chemistry, and hybridization are well known and commonly used in the art. Nucleic acid and peptide synthesis employs standard techniques. Generally, enzymatic reactions and purification steps are performed according to the manufacturer's instructions.

[0280] Embodiments of the invention have been disclosed in the accompanying drawings and description. Although specific terminology is used, it is for descriptive purposes only and not for limiting the invention, the scope of which is defined by the claims. It must be understood that the illustrated embodiments are for illustrative purposes only and should not be considered as limiting the invention. Those skilled in the art will understand that modifications, other embodiments, improvements, additions of details, and applications may be made to the invention in accordance with its text and spirit and within its scope; the scope of the invention is defined only by the claims and is interpreted in accordance with patent law (including the doctrine of equivalents). In the claims, reference characters used to indicate steps of the claims are provided for ease of description only and do not indicate any particular order in which these steps are performed (unless expressly stated otherwise).

[0281] In this document and its claims, the verbs “comprising,” “having,” and “containing,” and their various grammatical forms, are used in a non-limiting sense, indicating that everything that follows is included, but not excluded. The verb “substantially constitutes…” indicates, for example, that a composition as defined herein may contain additional components besides those explicitly specified, but which do not alter the distinctive features of the invention. In this document and its claims, unless otherwise expressly stated, the verbs “comprising,” “having,” and “containing,” and their various forms, are preferably replaced by “consisting of” (and their various forms) or “substantially constitutes” (and their various grammatical forms). Furthermore, when using the indefinite article to describe an element, the indefinite article “a” does not exclude the possibility of multiple elements, unless the context explicitly requires that there be one and only one such element. Therefore, the indefinite article “a” generally means “at least one.” When the terms “about,” “approximately,” or “around” are used with numerical values, parameters, or ranges of numerical values ​​(such as the amount, volume, volume ratio, volume percentage, weight ratio, weight percentage, or application rate of a component of a composition), they mean the expected amount, volume, volume ratio, volume percentage, weight ratio, weight percentage, or application rate that a person skilled in the art would consider to provide an effect equivalent to that obtained by a specified amount, volume, volume ratio, volume percentage, weight ratio, weight percentage, or application rate; and should be interpreted according to the number of significant figures reported and with the application of conventional rounding techniques. Preferably, when the terms “about,” “approximately,” or “around” are used with numerical values ​​(e.g., about 10), they preferably indicate that the value may be about 15% of a given value (10), preferably about 10%, more preferably about 5%, and even more preferably about 1%.

[0282] In the specification and claims, unless otherwise expressly stated, the expression "from x to y" (where x and y represent numerical values) refers to a range of values, in which both x and y are included, and where x represents the minimum value and y represents the maximum value. Therefore, the range includes x and y in addition to any values ​​between x and y.

[0283] The terms “LNT II”, “LNT-II”, “LN3”, “Lacto-N-trisaccharide II”, “Lacto-N-trisaccharide II”, “Lacto-N-trisaccharide”, “Lacto-N-trisaccharide” and “GlcNAc-β1,3-Gal-β1,4-Glc” can be used interchangeably.

[0284] The terms "LNT", "lacto-N-tetrasaccharide", and "lacto- N "-Tetrasaccharide" and "Gal-β1,3-GlcNAc-β1,3-Gal-β1,4Glc" can be used interchangeably.

[0285] The terms "LNnT", "lacto-N-neotetrasaccharide", and "lacto- N - The terms "neo-LNT" and "Galβ1-4GlcNAcβ1-3Galβ1-4Glc" can be used interchangeably.

[0286] The terms “lact-N-pentasaccharide” and “LN5” are used interchangeably and refer to GlcNAC-b1,3-Gal-b1,4-GlcNAC-b1,3-Gal-b1,4-Glc.

[0287] The terms “lact-N-neohexose” and “LNnH” are used interchangeably, referring to Gal-b1,4-GlcNAC-b1,6-(Gal-b1,4-GlcNAC-b1,3)-Gal-b1,4Glc.

[0288] The term "pLNnH" refers to Gal-b1,4-GlcNAC-b1,3-Gal-b1,4-GlcNAC-b1,3-Gal-b1,4-Glc.

[0289] The terms “para-lacto-N-neohexose II” and “pLNnH-II” are used interchangeably and refer to Gal-b1,4-GlcNAC-b1,3-Gal-b1,3-GlcNAC-b1,3-Gal-b1,4-Glc.

[0290] The term "pLNH" refers to Gal-b1,3-GlcNAC-b1,3-Gal-b1,4-GlcNAC-b1,3-Gal-b1,4-Glc.

[0291] The terms “p-lacto-N-hexasaccharide II” and “pLNH-II” are used interchangeably, referring to Gal-b1,3-GlcNAC-b1,3-Gal-b1,3-GlcNAC-b1,3-Gal-b1,4-Glc.

[0292] The term "pLNnO" refers to Gal-b1,4-GlcNAc-b1,3-Gal-b1,4-GlcNAc-b1,3-Gal-b1,4-GlcNAc-b1,3-Gal-b1,4-GlcNAc-b1,3-Gal-b1,4-Glc.

[0293] The term "pLNnD" refers to Gal-b1,4-GlcNAc-b1,3-Gal-b1,4-GlcNAc-b1,3-Gal-b1,4-GlcNAc-b1,3-Gal-b1,4-GlcNAc-b1,3-Gal-b1,4-GlcNAc-b1,3-Gal-b1,4-Glc.

[0294] The term "LNH" refers to Gal-b1,4-GlcNAC-b1,6-(Gal-b1,3-GlcNAc-b1,3)-Gal-b1,4-Glc.

[0295] The terms “lacto-N-biose” and “LNB” are used interchangeably and refer to Gal-b1,3-GlcNAc.

[0296] The terms “N-acetyllactosamine” and “LacNAc” are used interchangeably and refer to Gal-b1,4-GlcNAc.

[0297] The terms “iso-LNO” and “iso-lact-N-octasaccharide” are used interchangeably, referring to Gal-b1,3-GlcNAc-b1,3-(Gal-b1,3-GlcNAc-b1,3-Gal-b1,4-GlcNAc-b1,6-)Gal-b1,4-Glc.

[0298] The terms “LND” and “lact-N-decaose” are used interchangeably.

[0299] The terms “LNnD” and “lact-N-neodecanose” are used interchangeably.

[0300] The terms “2'-fucosylated lactose”, “2'-fucosylated lactose”, “α-1,2-fucosylated lactose”, “α-1,2-fucosylated lactose”, “α-1,2-fucosylated lactose”, “α-1,2-fucosylated lactose”, “Fuc-α1,2-Gal-β1,4-Glc”, “2FL” and “2'FL” are used interchangeably.

[0301] The terms “3-fucosyllactose”, “α-1,3-fucosyllactose”, “α-1,3-fucosyllactose”, “α-1,3-fucosyllactose”, “α-1,3-fucosyllactose”, “Gal-β1,4-(Fuc-α1,3-)Glc”, “3FL” and “3-FL” are used interchangeably.

[0302] The terms “di-fucosyllactose”, “di-fucosyllactose”, “lactodifucotetrasaccharide”, “2',3-di-fucosyllactose”, “2',3-di-fucosyllactose”, “α-2',3-fucosyllactose”, “α-2',3-fucosyllactose”, “Fuc-α1,2-Gal-β1,4-(Fuc-α1,3-)Glc”, “DFLac”, “2',3 diFL”, “DFL”, “DiFL”, and “diFL” are used interchangeably.

[0303] The terms “LNFP-I”, “Lact-N-fucopentose I”, “LNFP I”, “LNF I OH I type determinant”, “LNF I”, “LNF1”, “LNF 1”, “Blood group H antigen pentose type 1” and “Fuc-α1,2-Gal-β1,3-GlcNAc-β1,3-Gal-β1,4-Glc” can be used interchangeably.

[0304] The terms “GalNAc-LNFP-I”, “blood group A antigen hexasaccharide type I”, and “GalNAc-α1,3-(Fuc-α1,2)-Gal-β1,3-GlcNAc-β1,3-Gal-β1,4-Glc” can be used interchangeably.

[0305] The terms “Gal-LNFP-I”, “blood group B antigen hexasaccharide type I”, and “Gal-α1,3-(Fuc-α1,2)-Gal-β1,3-GlcNAc-β1,3-Gal-β1,4-Glc” can be used interchangeably.

[0306] The terms “LNFP-II”, “milk-N-fucopentose II”, and “Gal-β1,3-(Fuc-α1,4)-GlcNAc-β1,3-Gal-β1,4-Glc” are used interchangeably.

[0307] The terms “LNFP-III”, “milk-N-fucopentose III”, and “Gal-β1,4-(Fuc-α1,3)-GlcNAc-β1,3-Gal-β1,4-Glc” are used interchangeably.

[0308] The terms “LNFP-V”, “milk-N-fucopentose V”, and “Gal-β1,3-GlcNAc-β1,3-Gal-β1,4-(Fuc-α1,3)-Glc” are used interchangeably.

[0309] The terms "LNDFH I", "milk-N-difucohexose I", "LNDFH-I", "LDFH I", and "Le" are also mentioned. b"-Lactose", "Lewis-β-hexasaccharide" and "Fuc-α1,2-Gal-β1,3-[Fuc-α1,4]-GlcNAc-β1,3-Gal-β1,4-Glc" can be used interchangeably.

[0310] The terms “LNDFH II”, “milk-N-difucohexose II”, “Lewis a-Lewis x”, “LDFH II” and “Fuc-α1,4-(Gal-β1,3)-GlcNAc-β1,3-Gal-β1,4-(Fuc-α1,3)-Glc” are used interchangeably.

[0311] The terms “Lewis b-Lewis x” and “Fucα1,4-[Fuc-α1,2-Galβ1,3]-GlcNAc-β1,3-Gal-β1,4-[Fuc-α1,3]-Glc” are used interchangeably.

[0312] The terms “MFLNH III”, “monofucrose-milk-N-hexasaccharide-III”, and “Gal-β1,4-[Fuc-α1,3]-GlcNAc-β1,6-[Gal-β1,3-GlcNAc-β1,3]-Gal-β1,4-Glc” are used interchangeably.

[0313] The terms “DFLNH (a)”, “difucosyl lact-N-hexasaccharide (a)”, and “Gal-β1,4-[Fuc-α1,3]-GlcNAc-β1,6-[Fuc-α1,2-Gal-β1,3-GlcNAc-β1,3]-Gal-β1,4-Glc” are used interchangeably.

[0314] The terms “DFLNH”, “difucosyl lact-N-hexasaccharide”, and “Gal-β1,4-[Fuc-α1,3]-GlcNAc-β1,6-[Fuc-α1,4-[Gal-β1,3]-GlcNAc-β1,3]-Gal-β1,4-Glc” are used interchangeably.

[0315] The terms “TFLNH”, “trifucosyl lact-N-hexasaccharide”, and “Gal-β1,4-[Fuc-α1,3]-GlcNAc-β1,6-[Fuc-α1,4-[Fuc-α1,2-Gal-β1,3]-GlcNAc-β1,3]-Gal-β1,4-Glc” are used interchangeably.

[0316] The terms “LNnFP I”, “milk-N-neofofucopentose I”, and “Fuc-α1,2-Gal-β1,4-N-GlcNAc-β1,3-Gal-β1,4-Glc” are used interchangeably.

[0317] The terms “LNFP-VI”, “LNnFP V”, “milk-N-neofofucopentose V”, and “Gal-β1,4-GlcNAc-β1,3-Gal-β1,4-(Fuc-α1,3)-Glc” are used interchangeably.

[0318] The terms “LNnDFH”, “milk-N-neofucohexose”, “Lewis x hexose”, and “Gal-β1,4-(Fuc-α1,3)-GlcNAc-β1,3-Gal-β1,4-(Fuc-α1,3)-Glc” are used interchangeably.

[0319] The terms “2'-fucosylated lacto-N-disaccharide”, “2'FLNB”, and “Fuc-α1,2-Gal-β1,3-GlcNAc” are used interchangeably.

[0320] The terms “4-fucosylated lacto-N-disaccharide”, “4FLNB”, and “Fuc-α1,4-[Gal-β1,3-]GlcNAc” are used interchangeably.

[0321] The terms “difucosyl lact-N-disaccharide”, “diFLNB” and “Fuc-α1,4-[Fuc-α1,2-Gal-β1,3-]GlcNAc” are used interchangeably.

[0322] The terms “2'-fucosylosyl-N-acetyllactosamine”, “2'FlacNAc”, and “Fuc-α1,2-Gal-β1,4-GlcNAc” are used interchangeably.

[0323] The terms “3-fucosyl-N-acetyllactosamine”, “3FlacNAc”, and “Gal-β1,4-(Fuc-α1,3-)GlcNAc” are used interchangeably.

[0324] The terms “diFlacNAc” and “Fuc-α1,2-Gal-β1,4-[Fuc-α1,3-]GlcNAc” are used interchangeably.

[0325] The terms “3'-sialyl lactose”, “3'-sialyl lactose”, “α-2,3-sialyl lactose”, “α-2,3-sialyl lactose”, “α-2,3-sialyl lactose”, “α-2,3-sialyl lactose”, “3SL”, “Sia-α2,3-Gal-β1,4-Glc” and “3'SL” are used interchangeably.

[0326] The terms “6'-sialyl lactose”, “6'-sialyl lactose”, “α-2,6-sialyl lactose”, “α-2,6-sialyl lactose”, “α-2,6-sialyl lactose”, “α-2,6-sialyl lactose”, “6SL”, “Sia-α2,6-Gal-β1,4-Glc” and “6'SL” are interchangeable.

[0327] The terms “3,6-disialyllactose” and “Neu5Ac-α2,3-Neu5Ac-α2,6-Gal-β1,4-Glc” are used interchangeably.

[0328] The terms “6,6'-disialyllactose” and “Neu5Ac-α2,6-Neu5Ac-α2,6-Gal-β1,4-Glc” are used interchangeably.

[0329] The terms “8,3-disialyllactose” and “Neu5Ac-α2,8-Neu5Ac-α2,3-Gal-β1,4-Glc” are used interchangeably.

[0330] The terms “3'S-2'FL”, “3'-sialic acid-2'-fucosylated lactose”, and “Neu5Ac-α2,3-[Fuc-α1,2-]Gal-β1,4-Glc” are used interchangeably.

[0331] The terms “6'S-2'FL”, “6'-sialic acid-2'-fucosylated lactose”, and “Neu5Ac-α2,6-[Fuc-α1,2-]Gal-β1,4-Glc” are used interchangeably.

[0332] The terms “3'S-3-FL”, “3'-sialic acid-3-fucosylated lactose”, and “Neu5Ac-α2,3-Gal-β1,4-[Fuc-α1,3]Glc” are used interchangeably.

[0333] The terms “6'S-3-FL”, “6'-sialic acid-3-fucosylated lactose”, and “Neu5Ac-α2,6-Gal-β1,4-[Fuc-α1,3]Glc” are used interchangeably.

[0334] The terms “LSTa”, “LS-tetrasaccharide a”, “sialic acid-lact-N-tetrasaccharide a”, “sialic acid-lact-N-tetrasaccharide a” and “Neu5Ac-a2,3-Gal-b1,3-GlcNAc-b1,3-Gal-b1,4-Glc” are used interchangeably.

[0335] The terms “LSTb”, “LS-tetrasaccharide b”, “sialic acid-lact-N-tetrasaccharide b”, “sialic acid-lact-N-tetrasaccharide b” and “Gal-b1,3-(Neu5Ac-a2,6)-GlcNAc-b1,3-Gal-b1,4-Glc” are used interchangeably.

[0336] The terms “LSTc”, “LS-tetrasaccharide c”, “sialic acid-lact-N-tetrasaccharide c”, “sialic acid-lact-N-tetrasaccharide c”, “sialic acid-lact-N-neo-tetrasaccharide c” and “Neu5Ac-a2,6-Gal-b1,4-GlcNAc-b1,3-Gal-b1,4-Glc” are used interchangeably.

[0337] The terms “LSTd”, “LS-tetrasaccharide d”, “sialic acid-lact-N-tetrasaccharide d”, “sialic acid-lact-N-tetrasaccharide d”, “sialic acid-lact-N-neo-tetrasaccharide d” and “Neu5Ac-a 2,3-Gal-b1,4-GlcNAc-b1,3-Gal-b1,4-Glc” are used interchangeably.

[0338] The terms “3'-sialyl-N-disaccharide”, “3'SLNB”, and “Neu5Ac-a2,3-Gal-b1,3-GlcNAc” are used interchangeably.

[0339] The terms “6'-sialyl-N-disaccharide”, “6'SLNB”, and “Neu5Ac-a2,6-Gal-b1,3-GlcNAc” are used interchangeably.

[0340] The terms “monofucrose monosialot-N-octasaccharide”, “sialic acid Lewis a”, “sialic acid Lea”, “5-acetylneuraminic acid-(2-3)-galactosyl-(1-3)-(fucopyranosyl-(1-4))-N-acetylglucosamine” and “Neu5Ac-α2,3-Gal-β1,3-[Fuc-α1,4]-GlcNAc” are used interchangeably.

[0341] The terms “3’-sialyl lactosamine”, “3’SLacNAc”, and “Neu5Ac-a2,3-Gal-b1,4-GlcNAc” are used interchangeably.

[0342] The terms “6’-sialyl lactosamine”, “6’SLacNAc”, and “Neu5Ac-a2,6-Gal-b1,4-GlcNAc” are used interchangeably.

[0343] The terms “sialic acid Lewis x”, “sialic acid Lex”, “5-acetylneuraminic acid-(2-3)-galactosyl-(1-4)-(fucopyranosyl-(1-3))-N-acetylglucosamine” and “Neu5Ac-α2,3-Gal-β1,4-[Fuc-α1,3-]GlcNAc” are used interchangeably.

[0344] The terms “Neu4Ac”, “4-O-acetyl-5-amino-3,5-dideoxy-D-glycerol-D-galacto-non-2-onepyranoic acid”, and “4-O-acetylneuraminic acid” are used interchangeably, with the molecular formula C11H19NO9.

[0345] The terms “Neu5Ac”, “5-acetamino-3,5-dideoxy-D-glycerol-D-galacto-nonyl-2-onepyranoic acid”, “D-glycerol-5-acetamino-3,5-dideoxy-D-galacto-nonyl-2-onepyranoic acid”, “5-(acetamino)-3,5-dideoxy-D-glycerol-D-galacto-2-nonyl-onepyranoic acid”, “5-(acetamino)-3,5-dideoxy-D-glycerol-D-galacto-2-nonyl-onepyranoic acid”, “5-(acetamino)-3,5-dideoxy-D-glycerol-D-galacto-nonyl-2-onepyranoic acid”, and “5-(acetamino)-3,5-dideoxy-D-glycerol-D-galacto-nonyl-2-onepyranoic acid” are used interchangeably, and the molecular formula is C11H19NO9.

[0346] The terms “Neu4,5Ac2”, “N-acetyl-4-O-acetylneuraminic acid”, “4-O-acetyl-N-acetylneuraminic acid”, “4-O-acetyl-N-acetylneuraminic acid compound”, “4-acetylamino-3,5-dideoxy-D-glycerol-D-galacto-nonyl ketone acid compound”, “4-acetylamino-3,5-dideoxy-D-glycerol-D-galacto-2-nonyl ketone acid compound”, “4-acetylamino-3,5-dideoxy-D-glycerol-D-galacto-2-nonyl ketone acid”, and “4-acetylamino-3,5-dideoxy-D-glycerol-D-galacto-2-nonyl ketone acid” are used interchangeably, with the molecular formula C13H21NO10.

[0347] The terms “Neu5,7Ac2”, “7-O-acetyl-N-acetylneuraminic acid”, “N-acetyl-7-O-acetylneuraminic acid”, “7-O-acetyl-N-acetylneuraminic acid compound”, “7-acetylamino-3,5-dideoxy-D-glycerol-D-galacto-nonyl ketone acid compound”, “7-acetylamino-3,5-dideoxy-D-glycerol-D-galacto-2-nonyl ketone acid compound”, “7-acetylamino-3,5-dideoxy-D-glycerol-D-galacto-2-nonyl ketone acid”, and “7-acetylamino-3,5-dideoxy-D-glycerol-D-galacto-2-nonyl ketone acid” are used interchangeably in this document, and the molecular formula is C13H21NO10.

[0348] The terms “Neu5,8Ac2” and “5-n-acetyl-8-o-acetylneuraminic acid” are used interchangeably in this document, with the molecular formula C13H21NO10.

[0349] The terms “Neu5,9Ac2”, “N-acetyl-9-O-acetylneuraminic acid”, “9-anana”, “9-O-acetylsialic acid”, “9-O-acetyl-N-acetylneuraminic acid”, “5-n-acetyl-9-O-acetylneuraminic acid”, “N,9-O-diacetylneuraminic acid” and “N,9-O-diacetylneuraminic acid” are used interchangeably in this document, and the molecular formula is C13H21NO10.

[0350] The terms “Neu4,5,9Ac3” and “5-N-acetyl-4,9-di-O-acetylneuraminic acid” are used interchangeably in this document.

[0351] The terms “Neu5,7,9Ac3” and “5-N-acetyl-7,9-di-O-acetylneuraminic acid” are used interchangeably in this document.

[0352] The terms “Neu5,8,9Ac3” and “5-N-acetyl-8,9-di-O-acetylneuraminic acid” are used interchangeably in this document.

[0353] The terms “Neu4,5,7,9Ac4” and “5-N-acetyl-4,7,9-tri-O-acetylneuraminic acid” are used interchangeably in this document.

[0354] The terms “Neu5,7,8,9Ac4” and “5-N-acetyl-7,8,9-tri-O-acetylneuraminic acid” are used interchangeably in this document.

[0355] The terms “Neu4,5,7,8,9Ac5” and “5-N-acetyl-4,7,8,9-tetra-O-acetylneuraminic acid” are used interchangeably in this document.

[0356] Terms “Neu5Gc”, “N-hydroxyacetyl-neuraminic acid”, “N-hydroxyacetylneuraminic acid”, “N-hydroxyacetylneuraminic acid compound”, “N-ethanolyl-neuraminic acid compound”, “N-ethanolyl-neuraminic acid”, “N-ethanolylneuraminic acid”, “3,5-dideoxy-5-((hydroxyacetyl)amino)-D-glycerol-D-galacto-2-nonylpyranonic acid”, “3,5-dideoxy-5-(ethanolylamino)-D-glycerol-D-galacto-2-nonylpyranonic acid”, “3,5-dideoxy-5-(ethanolylamino)-D-glycerol-D-galacto-2-nonylpyranonic acid”, “3,5-Dideoxy-5-[(hydroxyacetyl)amino]-D-glycerol-D-galacto-non-2-onepyranoic acid” and “D-glycerol-5-hydroxyacetylamino-3,5-Dideoxy-D-galacto-non-2-onepyranoic acid” can be used interchangeably, with the molecular formula C11H19NO10.

[0357] The terms “DSLNnT” and “disialial lact-N-neotetrasaccharide” are used interchangeably, referring to Neu5Ac-a2,6-[Neu5Ac-a2,6-Gal-b1,4-GlcNAc-b1,3]-Gal-b1,4-Glc.

[0358] The terms “DSLNT” and “disialial lacto-N-tetrasaccharide” are used interchangeably, referring to Neu5Ac-a2,6-(Neu5Ac-a2,3-Gal-b1,3-)GlcNAc-b1,3-Gal-b1,4-Glc.

[0359] The terms “DS'LNT” and “disialiolact-N-tetrasaccharide analogue” are used interchangeably, referring to Neu5Ac-a2,6-(Neu5Ac-a2,6-Gal-b1,3-GlcNAc-b1,3-)Gal-b1,4-Glc.

[0360] The terms “DS'LNnT” and “disialiolact-N-neotetrasaccharide analog” are used interchangeably, referring to Neu5Ac-a2,6-(Neu5Ac-a2,3-Gal-b1,4-GlcNAc-b1,3-)Gal-b1,4-Glc.

[0361] The terms “Gal” refers to galactose, “GlcNAc” refers to N-acetylglucosamine, “Neu5Ac” refers to N-acetylneuraminic acid, “Glc” refers to glucose, “ManNAc” refers to N-acetylmmannosamine, “GalNAc” refers to N-acetylgalactosamine, “Fuc” refers to fucose, and “LacNAc” refers to N-acetyllactosamine.

[0362] Example The invention will be described in more detail with reference to embodiments. The following embodiments are intended to further illustrate and explain the invention, and are not intended to limit the invention in any way.

[0363] Example 1 : Saccharides 3'-Sialyllactose (3'SL) and 6'-Sialyllactose (6'SL) were prepared as described in WO2022 / 034079 (Examples 11, 13, and 14; Escherichia coli strains: for 6'SL, described in Example 3 of WO2018 / 122225; for 3'SL, described in Example 7 of WO2018 / 122225), wherein strains derived from Pasteurella multocida ( Pasteurella multocida The α-2,3-sialyl transferase (amino acids 1-268 of Uniprot ID Q9CLP3 sequence v1) was recombinantly produced and purified in *E. coli*, and then dried according to Example 21 of WO2022 / 034079 to obtain 3'SL monosodium powder (purity 98.4%; 83.68% w / w, determined by quantitative NMR) and 6'SL monosodium powder (purity 98.6%; 82.64% w / w, determined by quantitative NMR). Throughout the Examples section, the "purity" of carbohydrates is expressed as purity relative to the total carbohydrate content. For example, 6'SL powder with a purity of 98.6% means that 6'SL accounts for 98.6% of the total carbohydrate content of the powder.

[0364] Lactosyl sialate a (LST a) was recombinantly produced in Escherichia coli and purified as described in Example 4 of EP23180784.3, and then dried as described in Example 21 of WO2022 / 034079 to obtain LST a monosodium powder (purity 89.8%).

[0365] Lacto-sialotetrate c (LST c) was recombinantly produced in Escherichia coli as described in WO2022 / 034079 (Examples 11, 13 and 14), purified, and then dried as described in Example 21 of WO2022 / 034079 to obtain LST c monosodium powder (purity 97.3%).

[0366] 3'KDO-lactose was recombinantly produced in E. coli as described in WO2023 / 187109 (Examples 14 and 15) and purified, and then dried as described in Example 21 of WO2022 / 034079 to obtain 3'KDO-lactose monosodium powder (purity 78.5%).

[0367] 3'-Sialo-3-fucosylated lactose (3'S-3-FL) was recombinantly produced in Escherichia coli as described in Example 10 of PCT / EP2024 / 053033, but in a bioreactor as described in Example 1 of PCT / EP2024 / 053033, and then purified and dried as described in Example 21 of WO2022 / 034079 to obtain 3'S-3-FL powder (purity 90%; 80.0% w / w, determined by quantitative NMR).

[0368] 2'-Fucosyllactose (2'FL) was recombinantly produced and purified in Escherichia coli as described in Examples 10, 13 and 14 of WO2022 / 034079, and then dried as described in Example 21 of WO2022 / 034079 to obtain 2'FL powder (purity 99.3%; 97.79% w / w, determined by quantitative NMR).

[0369] 3-Fucosyllactose (3-FL) was recombinantly produced in Escherichia coli as described in Example 16 of WO2020 / 127417 (Helicobacter pylori α-1,3-fucosyltransferase), purified as described in Examples 13-20 of WO2022 / 034079, and then dried as described in WO2019 / 160922 (Example 7) to obtain 3-FL powder (purity 96.75%; 90.34% w / w, determined by quantitative NMR).

[0370] Saccharide analysis Standards were purchased from Carbosynth (UK), Elicityl (France), and IsoSep (Sweden). Other compounds were analyzed using in-house prepared standards.

[0371] Neutral oligosaccharides were analyzed on a WatersAcquity H-class UPLC equipped with an evaporative light scattering (ELSD) detector or a refractive index (RI) detector. 0.7 µL of sample was injected into a WatersAcquity UPLC BEH Amide column (2.1 × 100 mm; 130 Å; 1.7 µm) equipped with an Acquity UPLC BEH Amide VanGuard column (130 Å, 2.1 × 5 mm). The column temperature was 50 °C. The mobile phase consisted of 1 / 4 water and 3 / 4 acetonitrile solution with 0.2% triethylamine added. Isocratic elution was performed at a flow rate of 0.130 mL / min. The ELS detector was set to a drift tube temperature of 50 °C, a nitrogen pressure of 50 psi, a gain of 200, and a data acquisition rate of 10 pps. The RI detector was set to 35 °C.

[0372] Sialized oligosaccharides were analyzed on a Waters Acquity H-class UPLC equipped with a refractive index (RI) detector. 0.5 µL of sample was injected into a Waters Acquity UPLC BEH Amide column (2.1 × 100 mm; 130 Å; 1.7 µm). The column temperature was 50 °C. The mobile phase consisted of a mixture of 70% acetonitrile, 26% ammonium acetate buffer (150 mM), and 4% methanol, with 0.05% pyrrolidine added. Isocratic elution was performed at a flow rate of 0.150 mL / min. The RI detector temperature was set to 35 °C.

[0373] Neutral and sialylated sugars were analyzed on a Waters Acquity H-class UPLC equipped with a refractive index (RI) detector. 0.5 µL of sample was injected into a Waters Acquity UPLC BEH Amide column (2.1 × 100 mm; 130 Å; 1.7 µm). The column temperature was 50 °C. The mobile phase consisted of a mixture of 72% acetonitrile and 28% ammonium acetate buffer (100 mM), with 0.1% triethylamine added. Isocratic elution was performed at a flow rate of 0.260 mL / min. The RI detector temperature was set to 35 °C.

[0374] The purity of the target sugar is calculated using the following formula: [AUC (target sugar) / AUC (sugar of each type detected)] 100%. “AUC” refers to the “Area Under the Curve”.

[0375] Quantitative NMR The weight percentage (% w / w) of the target sugars in the total powder mass was determined by qNMR.

[0376] NMR spectra were recorded on a Bruker Avance Neo 400MHz equipped with SmartProbe.

[0377] Spectra were processed using TopSpin v4.1.1 (Bruker BioSpin GmbH). Deuterated water (D2O, 99.9%D), maleic acid (TraceCERT, Supelco, lot number BCCC6481, purity 99.94%), and 5 mm glass NMR tubes (Wilmad, 400 MHz) were purchased from Sigma Aldrich. An analytical balance with an accuracy of 0.1 mg was used for sample preparation.

[0378] Prepare samples in triplicate. The analyte (HMO) was analyzed directly; no drying or other treatment was performed on the samples before preparation. Accurately weigh approximately 50 mg of HMO and approximately 25 mg of internal standard (maleic acid) and place them together in a 3 mL glass vial. Add 500 µL of deuterated water (D2O) and shake the vial until all solids are dissolved. Transfer 125 µL of the resulting clear, colorless solution to an NMR tube, add 475 µL of D2O, and carefully vortex to mix the contents.

[0379] The spectrum was recorded at 400 MHz at a temperature of 298 K, without rotation (rotator frequency = 0), with the following parameters and settings: - Flip angle: 30° -Number of scans: 32 - Relaxation delay: 20s.

[0380] Import raw data in Bruker data file format into TopSpin, where the software automatically performs Fourier transform and phase correction. No manual phase correction or other forms of baseline correction are required. For quantitative analysis, manually integrate the two signals (excluding their...). 13 C satellite peak), and calculate the purity (mass fraction percentage) of HMO as follows:

[0381] -w X The purity (% m / m) of the HMO analyte to be tested. -I X and I S These are the integral values ​​of the quantitative HMO and internal standard signals, respectively. -N X and N S It is the number of protons (1H nuclei) that contribute to the quantitative signal of HMO and internal standard (maleic acid has 2 protons). -M X and M S The molecular weights of HMO and internal standard -m X and m S It is the mass of HMO and internal standard in the qNMR sample. -w S It is the (known) purity of the internal standard.

[0382] Example 2: Biotic stimulation Setting up the experiment Wheat (Quintus variety), corn (Like it variety), and soybean (Lenka variety) seeds were coated in a Satec ML2000 seed treatment machine (8 liters of formulation per ton of seed). The formulation consisted of an 8% (v / v) aqueous solution of polyvinyl alcohol and different concentrations of sugars (see Example 1) as “single treatment” or different combinations of different sugar concentrations (see Example 1) as “combination treatment”. The coated seeds were then sown in 96-cell seedling trays filled with standard potting soil. Each tested sugar concentration or combination was tested in eight replicates, with six plants per replicate.

[0383] Results Stem length (cm) and biomass (canopy fresh weight; g), as well as the ratio of fresh weight to stem length, were measured at different days after sowing (DAS) to assess plant robustness. Results are shown as a percentage compared to the untreated control (UTC, i.e., the formulation without the tested sugar), which was set at 100%. Table 1 shows the results for individual treatments of wheat (quintus variety), maize (Likeit variety), and soybean (lenka variety), while Table 2 shows the results for combined treatments. Unless otherwise explicitly stated, in all examples, the untreated control (UTC) refers to the plant or plant part receiving the formulation without the tested sugar.

[0384] Table 1. Results of biostimuli treated individually.

[0385] “DAS” = Days after sowing; “UTC” = Untreated control; “Dosage” represents the amount of each tested sugar per ton of seed. “7 / 14 DAS”: 7 days for wheat (Quintus variety), and 14 days for corn (Like it variety) and soybean (Lenka variety). “14 / 21 DAS”: 14 days for wheat (Quintus variety), and 21 days for corn (Like it variety) and soybean (Lenka variety).

[0386]

[0387] Table 2. Results of biostimulation from combined treatments.

[0388] “DAS” = Days after sowing; “UTC” = Untreated control; “Dosage” indicates the amount of each tested sugar per ton of seed.

[0389]

[0390] Example 3: Biotic stimulation (abiotic stress) Setting up the drought / flooding experiment For foliar treatment, corn (Mofox or Mon Chérie) seeds or wheat (Chevignon) seeds were sown in seedling trays (12×8) containing a substrate supplemented with perlite. Ten days later, when the plants had two grown leaves, foliar spraying was performed by spraying with aqueous solutions of different concentrations of sugars (see Example 1), or aqueous solutions of different concentrations of different sugars (see Example 1). A spray chamber equipped with an Albuz ADI 100° drift-reducing nozzle was used to simulate field application at 200 liters per hectare.

[0391] For seed treatment, maize (variety mofox) seeds were coated using a Satec ML2000 seed treatment machine (8 liters of formulation per ton of seeds). The formulation consisted of an 8% (v / v) aqueous solution of polyvinyl alcohol and sugars of varying concentrations (see Example 1) or combinations of different sugars of varying concentrations (see Example 1). The coated seeds were then sown in seedling trays (12×8) containing a substrate supplemented with perlite.

[0392] Three days after foliar treatment (foliar treatment experiment) or approximately 13 days after sowing (seed coating experiment), the plants were planted in P9 pots and placed under the following conditions: -Drought: Place the plants in plastic containers without watering. When the first signs of drought appear, water each pot with 100 mL. - Flooding: Place the plant in a plastic container filled with water. Adjust the water level to the height of the pot, ensuring the substrate is submerged. If yellowing leaves appear, place the plant under intermittent flooding conditions (21 liters of water per 2.5 m² for 2 minutes every 24 hours). 2 ).

[0393] - Intermittent flooding system: This is used to test growth-promoting effects under "normal conditions".

[0394] Climate conditions in a greenhouse: - Temperature: 22℃ (daytime) / 10℃ (nighttime) Humidity: 50% relative humidity -Covering: ○300 W / m² = 30% shading rate ○500 W / m² = 50% shading rate 700 W / m² = 70% shading rate ○900 W / m² = 90% shading rate The stem length, chlorophyll content, biomass (i.e., canopy fresh weight), and water content per pot were assessed. Measurements were taken on the first day after transplanting (i.e., the initial measurement) and then every 3-4 days for 3-4 weeks.

[0395] Setting up the frost experiment Strawberries (Sonata / Elsanta / Flair varieties) were grown in standard strawberry substrate (one plant per P13 pot) with added Osmocoat (18-5-11 + 4CaO + 2MgO Agroblen; 180 g / 65 L substrate). The pots were placed in an intermittent flooding system (every 2.5 m³ every 10 minutes). 2 Apply 21 liters of water (twice every 24 hours). Foliar spraying (aqueous solutions of different sugar concentrations (see Example 1), or aqueous solutions of different combinations of different sugar concentrations (see Example 1)) is carried out at the early growth stage (approximately 1 week after planting), 1 day before frost, or 10 days before frost. A spray chamber equipped with an Albuz ADI 100° drift reducer is used to simulate field application of 200 liters per hectare. At full bloom, each branch at the same phenological stage is marked, and the plants are placed on trays in a 5°C freezer overnight (with cushioning plants around the trays). In the morning, after refrigerating the plants, they are placed in freezer containers at -5°C. A temperature recorder is placed between the plants. When the temperature reaches -3°C, the freezing temperature is set to -3°C. After freezing at -3°C for one hour, the plants are removed from the containers. One day and one week after the frost, the percentage of damaged flowers on the marked branches is assessed. In addition, when the fruit is ripe, mature fruit is harvested and assessed (the number and weight of primary and secondary fruit on the marked branches and the rest of the plant are counted separately). After three harvests, the number of flowering branches, immature fruit, and stolons is also assessed.

[0396] Climate conditions in a greenhouse: - Temperature: 22℃ (daytime) / 10℃ (nighttime) Humidity: 50% relative humidity - Shading effect: ○300 W / m² = 30% shading rate ○500 W / m²= Shading rate 700 W / m² = 70% shading rate ○900 W / m² = 90% shading rate Results Tables 3 (Follicular Treatment) and 4 (Seed Treatment) show the growth of maize during the stress period (GS), recovery period (GR), and test period (GT) (i.e., plant length at the end of the specified period minus plant length at the beginning of the specified period), expressed as a percentage compared to the untreated control (UTC, i.e., no sugar application), which is set at 100%. For example, the growth during the stress period is calculated as: plant length at the beginning of recovery minus plant length before the start of stress.

[0397] Table 3. Biostimulation results (foliar treatment) of maize (varieties Mofox or Mon Chérie) under different abiotic stress conditions. “UTC” = untreated control; “dosage” indicates the amount of each tested sugar per hectare; “GS” = growth during stress; “GR” = growth during recovery; “GT” = growth during the test.

[0398]

[0399] Table 4. Biostimulation results (seed treatment) of maize (variety Mofox) under different abiotic stress conditions. “UTC” = untreated control; “dosage” indicates the amount of each tested sugar per hectare; “GS” = growth during stress; “GR” = growth during recovery; “GT” = growth during the test.

[0400]

[0401] Table 5 shows the number of healthy flowers, first-grade fruits, and fruit weight of strawberries (after frost stress) treated with sugars (foliar treatment), expressed as a percentage compared to the untreated control (UTC, i.e., no sugar application) (set as 100%).

[0402] Table 5. Biostimulation results of strawberry (varieties Sonata / Elsanta / Flair) under frost stress. “UTC” = untreated control; “dosage” indicates the amount of sugar per hectare per test; “ / ” indicates no fruit was harvested on the marked branch.

[0403]

[0404]

[0405] Example 4: Biotic stress Laboratory experiment Wheat (variety Feeling) or rapeseed (variety Helga) seeds were coated in a Satec ML2000 seed treatment machine (8 liters of formulation per ton of seeds). The formulation consisted of an 8% (v / v) aqueous solution of polyvinyl alcohol and different concentrations of sugars (see Example 1) or combinations of different concentrations of different sugars (see Example 1). Each concentration was repeated four times. Five seeds were placed on moistened filter paper in a petri dish. The seeds were germinated in an incubator at 20°C with a 12-hour light / 12-hour dark cycle. Four days after the start of the experiment, seedlings were inoculated with a spore suspension of the pathogen (for wheat, Fusarium solani, *Fusarium solani*). Fusarium culmorum FUSACU); for rapeseed, use semi-live nutrient-type spotted cocci ( Leptosphaeria maculans (i.e., LEPTMA), with a concentration of 1×10 5 1 spore / ml in 1 / 8 potato glucose broth. Add 3 ml of spore suspension to each petri dish to ensure infection. Monitor plant health daily after infection until two weeks after inoculation. Compare treated plants with untreated healthy seedlings and untreated infected seedlings. Results are the percentage of healthy plants compared to untreated infected seedlings (efficacy).

[0406] Greenhouse experiment For foliar treatment, wheat (Benchmark or Bennington) seeds were sown in potting soil, 4 seeds per pot. Each test concentration was tested in 5 replicates. Fifteen days after sowing, foliar application was performed by spraying with aqueous solutions of different concentrations of sugars (see Example 1) or aqueous solutions of different concentrations of different combinations of sugars (see Example 1). Field application was simulated at 200 liters per hectare using a spray chamber equipped with an Albuz ADI 100° drift-reducing nozzle.

[0407] For seed treatment, wheat (benchmark) seeds were coated in a Satec ML2000 seed treatment machine (8 liters of formulation per ton of seeds). The formulation consisted of an 8% (v / v) aqueous solution of polyvinyl alcohol and different concentrations of sugars (see Example 1) or combinations of different concentrations of different sugars (see Example 1). The coated seeds were then sown in potting soil: 4 seeds per pot. Each test concentration was tested in 5 replicates.

[0408] Three days after foliar treatment (foliar treatment test) or 18 days after sowing (seed coating test), the concentration used is 1×10⁻⁶. 5 Spores / mL of the live vegetative fungus *Cryptospora spp.* (wheat rust) Puccinia triticinaPlants were inoculated with a spore suspension of PUCCRT until dripping. Plants were assessed at 11, 13, and 21 days post-inoculation after the appearance of initial symptoms. The percentage of PUCCRT spots on the top four leaves of the plant (i.e., infection severity) was determined. The mean severity of the top four leaves per plant was calculated. The overall efficacy of each treatment was calculated as a percentage compared to the untreated infected control.

[0409] Detached leaf experiment For foliar treatment, potatoes (variety Fontane) were sown (1 plant per pot). Four replicates were applied for each experimental concentration. Foliar application was carried out two weeks after sowing by spraying with aqueous sugar solutions of varying concentrations. Field application was simulated at 200 liters per hectare using a spray chamber equipped with an Albuz ADI 100° drift-reducing nozzle.

[0410] Three days after foliar treatment, place the terminal leaflets of the third and fifth leaves of each plant onto water agar in a petri dish. Then use a 1×10⁻⁶ solution. 5 Phytophthora infestans ( spores / mL) Phytophthora infestans Spray the leaves with a spore suspension of PHYTIN until the leaves are completely covered by the suspension. Incubate the petri dishes at 15°C and 80% RH.

[0411] The experiment was evaluated 16 days post-inoculation. Phytin percentage (i.e., infection severity) was determined. The mean severity was calculated for four leaves in each treatment. The overall efficacy of each treatment was calculated as a percentage compared to the untreated infected control.

[0412] Growth chamber insect experiment Pea plants (Norli variety) were sown in pots of 4 seeds per pot. Foliar application was performed by spraying with sugar solutions of varying concentrations until dripping. A Birchmeier sprayer was used for each treatment. Three days after treatment, two pots of plants from each treatment were placed in an insect tent. Each tent contained 15 beet armyworms (Spodoptera litura). Spodoptera exigua Larvae. After 7 days, larval survival rate and average larval weight were assessed. Weight loss was calculated based on comparison with the untreated control. Survival percentage was calculated based on the initial number of larvae per tent (n=15).

[0413] Results Tables 6 (Laboratory tests: wheat and rapeseed), 7 (Greenhouse tests: wheat variety Benchmark), 8 (Greenhouse tests: wheat variety Bennington), 9 (Ex vivo leaf tests: potato), and 10 (Grow chamber insect tests) show the efficacy of different sugars in protecting plants against plant pathogens.

[0414] Table 6. Efficacy of sialylated sugars in protecting wheat (variety Feeling) and rapeseed (variety Helga) against pathogens (laboratory test). “FUSACU” = Fusarium oxysporum; “LEPTMA” = Micrococcus spectabilis; “UTC” = untreated control.

[0415]

[0416] Table 7. Efficacy of sialylated sugars in protecting wheat (variety Benchmark) against wheat cryptic rust (greenhouse trial). “UTC” = untreated control.

[0417]

[0418] Table 8. Efficacy of sialylated sugars in protecting wheat (behington variety) against wheat cryptic rust (greenhouse trial). “UTC” = untreated control.

[0419]

[0420] Table 9. The protective effect of sialylated sugars on potato (variety Fontane) against Phytophthora blight (ex-leaf test). “UTC” = untreated control.

[0421]

[0422] Table 10. Efficacy of sialylated sugars in protecting peas (variety Norli) against beet armyworm larvae (growth chamber insect experiment). "UTC" = untreated control.

[0423]

Claims

1. A plant treatment method, wherein the method includes the step of applying a sialic acid-containing sugar to the plant, a portion of the plant, a seed of the plant, and / or a desired growth area of ​​the plant, wherein the degree of polymerization (DP) of the sialic acid-containing sugar is at least 2, and wherein the sialic acid-containing sugar comprises sialic acid linked to a monosaccharide via an α-2,3-, α-2,6-, or α-2,8- bond, wherein the monosaccharide is selected from galactose, N-acetylglucosamine, and sialic acid.

2. The method according to claim 1, wherein the sialic acid is 9-carbon sialic acid or 8-carbon sialic acid, preferably 9-carbon sialic acid.

3. The method according to claim 2, wherein the nine-carbon sialic acid is selected from the list consisting of N-acetylneuraminic acid (Neu5Ac), Neu4Ac, Neu4,5Ac2, Neu5,7Ac2, Neu5,8Ac2, Neu5,9Ac2, Neu4,5,9Ac3, Neu5,7,9Ac3, Neu5,8,9Ac3, Neu4,5,7,9Ac4, Neu5,7,8,9Ac4, Neu4,5,7,8,9Ac5, and Neu5Gc, preferably, wherein the nine-carbon sialic acid is N-acetylneuraminic acid (Neu5Ac).

4. The method according to claim 2, wherein the octacarbon sialic acid is ketodeoxyoctanoic acid (KDO).

5. The method according to any one of claims 1 to 4, wherein the sialic acid-containing sugar comprises lactose, lacto-N-biose (LNB), or N-acetyllactosamine (LacNAc).

6. The method according to any one of claims 1 to 5, wherein the sialic acid-containing sugar comprises an oligosaccharide selected from the list consisting of 3'SL, 6'SL, 3'SLNB, 6'SLNB, 3'SLacNAc, 6'SLacNAc, 3'KDO-lactose, 6'KDO-lactose, 3'KDO-LNB, 6'KDO-LNB, 3'KDO-LacNAc, and 6'KDO-LacNAc; optionally, wherein the oligosaccharide further comprises one or more additional monosaccharides, the monosaccharides preferably selected from glucose, galactose, N-acetylglucosamine, N-acetylglucosamine, fucose, and sialic acid.

7. The method according to any one of claims 1 to 6, wherein the sialic acid-containing sugar is selected from 3'-sialyl-lactose (3'SL), 6'-sialyl-lactose (6'SL), 3,6-disialyl-lactose, 6,6'-disialyl-lactose, 8,3-disialyl-lactose, 3'S-2'FL, 6'S-2'FL, 3'S-3-FL, 6'S-3-FL, Neu5Ac-α-2,6-(GlcNAc-β-1,3-)Gal-β-1,4-Glc, Neu5Ac-α-2,6-(Neu5Ac-α-2,3-)Gal-β-1,4-Glc, LST a, LST b, LST c, LST d. A list consisting of bis(sialo-lact-N-tetrasaccharide) (DSLNT), bis(sialo-lact-N-tetrasaccharide) analog (DS'LNT), bis(sialo-lact-N-neo-tetrasaccharide) (DSLNnT), bis(sialo-lact-N-neo-tetrasaccharide) analog (DS'LNnT), 3'-sialo-lact-N-biose (3'SLNB), 6'-sialo-lact-N-biose (6'SLNB), sialic acid Lewis a, 3'-sialo-lactosamine (3'SLacNAc), 6'-sialo-lactosamine (6'SLacNAc), sialic acid Lewis x, 3'KDO-lactose, 6'KDO-lactose, 3'KDO-LNB, 6'KDO-LNB, 3'KDO-LacNAc and 6'KDO-LacNAc; optionally, said sialic acid-containing sugars further comprise fucose.

8. The method according to any one of claims 1 to 7, wherein the application step is seed application, root application, air application, or soil application.

9. The method according to any one of claims 1 to 8, wherein the application step is seed application or aerial application.

10. The method according to any one of claims 1 to 9, wherein the application step comprises one or more selected from watering, spraying (including ultra-low volume spraying), irrigation, atomization, spraying, dusting, foaming, spreading, coating, immersion, drip irrigation, and injection.

11. The method according to any one of claims 1 to 10, wherein the application step includes coating, preferably by spraying.

12. The method according to any one of claims 1 to 10, wherein the sialic acid-containing sugar is part of the composition.

13. The method according to any one of claims 1 to 12, wherein the method is for promoting the growth and / or development of a plant or a part of a plant.

14. The method of claim 13, wherein the growth and / or development refers to one or more of improving plant yield, improving fruiting ability, improving flower development, and improving toughness.

15. The method according to any one of claims 1 to 12, wherein the method is for protecting a plant or parts of a plant against abiotic and / or biotic stresses.

16. The method according to any one of claims 1 to 12, wherein the method is for protecting a plant or a portion of a plant against abiotic stresses selected from the list of frost, drought, osmotic stress (preferably salt), humidity (preferably flooding), heat stress, light stress (preferably ultraviolet stress), and mechanical stress.

17. The method according to any one of claims 1 to 12, wherein the method is for protecting a plant or a part of a plant against biotic stress.

18. The method according to claim 15 or 17, wherein the biological stress includes plant pathogens or diseases caused by said plant pathogens.

19. The method according to any one of embodiments 1 to 17, wherein the method further comprises the step of applying one or more additional sugars to the plant, a portion of the plant, the seeds of the plant, and / or the intended growth area of ​​the plant.

20. The method of claim 19, wherein the method comprises the step of applying (i) a fucosylated sugar and / or (ii) a non-fucosylated sugar and / or (iii) a monosaccharide and / or (iv) a synthetic intermediate of the sialic acid-containing sugar.

21. The method of claim 19 or 20, wherein the method includes the step of applying a fucosylated sugar, the fucosylated sugar comprising fucose linked to a monosaccharide via an α-1,3-bond.

22. The method according to any one of claims 19 to 21, wherein the method includes the step of applying a fucosylated sugar, the fucosylated sugar comprising fucose linked to a monosaccharide via an α-1,2-bond.

23. Use of a sialic acid-containing sugar as a biostimulant for plant growth and / or plant development, wherein the degree of polymerization (DP) of the sialic acid-containing sugar is at least 2, and wherein the sialic acid-containing sugar comprises sialic acid linked to a monosaccharide via an α-2,3-, α-2,6-, or α-2,8- bond, wherein the monosaccharide is selected from galactose, N-acetylglucosamine, and sialic acid.

24. Use of a sialic acid-containing sugar as a plant protectant, wherein the degree of polymerization (DP) of the sialic acid-containing sugar is at least 2, and wherein the sialic acid-containing sugar comprises sialic acid linked to a monosaccharide via an α-2,3-, α-2,6-, or α-2,8- bond, wherein the monosaccharide is selected from galactose, N-acetylglucosamine, and sialic acid.

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