Ascaroside and phytonutrient combinations and methods of use

Abstract

Provided herein are combinations of agents for enhancing plant growth and methods of using the same. The combination comprises at least one ascaroside (or a derivative or analog of the ascaroside) and at least one phytonutrient. The one or more ascarosides and the one or more phytonutrients may be provided in the same composition, or may be applied together (e.g., substantially simultaneously) or sequentially.

Description

[0001] Cross-references to related applications

[0002] This application claims priority to U.S. Provisional Application No. 63 / 515,554, filed July 25, 2023, the entire contents of which are hereby incorporated by reference. Technical Field

[0003] This invention relates to compositions and methods related to the use of ascaroside and one or more phytonutrients. Background Technology

[0004] Phytonutrients are essential for plant growth and development, as well as the production and quality of their flowers and fruits. Plants also require phytonutrients to produce chlorophyll and perform photosynthesis.

[0005] Many essential and beneficial phytonutrients are known, each playing a vital role in promoting the growth and development of plants, flowers, and fruits. Typically, one or more phytonutrients are applied to any given production crop (“crop”) during its growth process. To effectively address phytonutrient deficiencies and prevent damage from pathogens in plant life, it is often necessary to apply these components individually. This is harmful because it requires additional processing by the crop, increasing costs, resource usage (e.g., fuel, water, labor, etc.), and potential damage to the crop and / or soil. Summary of the Invention

[0006] A combination of agents for promoting plant growth and a method of application are provided. The combination comprises at least one ascaroside (or a derivative or analog of ascaroside) and at least one phytonutrient. The ascaroside can be combined with at least one phytonutrient to provide the plant with the components required for its growth, while also providing durable protection against pathogens (e.g., fungi, molds, bacteria, viruses, and / or nematodes) throughout the plant's life. One or more ascarosides and one or more nutrients can be provided in the same composition, or can be applied together (i.e., substantially simultaneously) or sequentially. The agent is applied in an effective amount (i.e., an amount sufficient to provide the plant with one or more nutrients to promote growth and development and also to provide durable protection against pathogens).

[0007] The present invention includes, but is not limited to, the following embodiments.

[0008] Example 1: A method for providing nutrients to plants and protecting them against pathogens, the method comprising contacting the plant, plant parts or the soil surrounding the plant with an effective amount of a combination of agents comprising one or more ascarosides and one or more phytonutrients.

[0009] Example 2: According to the method of Example 1, wherein the one or more phytonutrients include one or more macronutrients selected from the group consisting of: nitrogen-containing nutrients, phosphorus-containing nutrients, potassium-containing nutrients, calcium-containing nutrients, magnesium-containing nutrients, sulfur-containing nutrients, and combinations thereof.

[0010] Example 3: The method according to Example 1 or 2, wherein the macronutrient is selected from nitrogen-containing nutrients, phosphorus-containing nutrients, potassium-containing nutrients, and combinations thereof.

[0011] Example 4: The method according to any one of Examples 1 to 3, wherein the one or more phytonutrients are in the form of a mixture of nitrogen-containing nutrients, phosphorus-containing nutrients and potassium-containing nutrients.

[0012] Example 5: The method described in Example 2, wherein the macronutrient is selected from calcium-containing nutrients, magnesium-containing nutrients, sulfur-containing nutrients, and combinations thereof.

[0013] Example 6: The method according to any one of Examples 1 to 5, wherein the one or more plant nutrients are in the form of manure / bird droppings, fish milk, bone meal, blood meal, bio-fertilizer or cover crop.

[0014] Example 7: The method according to any one of Examples 1 to 6, wherein the one or more phytonutrients comprises one or more micronutrients selected from the group consisting of: boron-containing nutrients, chlorine-containing nutrients, copper-containing nutrients, iron-containing nutrients, manganese-containing nutrients, molybdenum-containing nutrients, zinc-containing nutrients, and combinations thereof.

[0015] Example 8: The method according to any one of Examples 1 to 7, wherein the one or more phytonutrients comprise one or more macronutrients and one or more micronutrients.

[0016] Example 9: The method according to any one of Examples 1 to 8, wherein the one or more ascarosides comprises an ascaroside having structure (I):

[0017] Where Z is the C that has been substituted in an optional manner. 3-40 Aliphatic groups, and R a and R b Each of them is independently -H or an optionally substituted portion of a group consisting of the following: C 1-20 aliphatic, C 1-20 Acyl group, C 1-20 Heteroaliphatic, aryl, heteroaryl, hydroxyl protecting groups, phosphorus-linked functional groups, sulfur-linked functional groups, silicon-linked functional groups, C 2-20 Carbonates (e.g., partially -C(O)OR) c C 2-20Carbamates (e.g., partially -C(O)N(R) c )2) C 2-20 Thioesters (e.g., partially -C(S)R) c C 2-20 Thiocarbonates (e.g., partially -C(S)OR) c C 2-20 Dithiocarbonates (e.g., partially -C(S)SR) c C 1-20 Thiocarbamates (e.g., partially -C(S)N(R) c 2) The sugar moiety, peptide, polymer chain, or linker to another ascaridin molecule via a bond or carbon-containing linker. Among them, R... c Each occurrence is independently selected from -H, optionally substituted C. 1-12 Aliphatic, optionally substituted C 1-12 Heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, polymer chain or linkage to another ascaridin molecule via a bond or carbon-containing linker, wherein R a and R b Together they can form an optionally substituted ring, which optionally contains one or more heteroatoms and optionally contains one or more unsaturated sites.

[0018] Example 10: The method according to Example 9, wherein Z is selected from the group consisting of: i. –CH(CH3)–R 1 , where R 1 C is arbitrarily substituted 1-40 Aliphatic group, ii.–CH(CH3)–(CH2) n –CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides; iii. –CH(CH3)–(CH2) n –CH=CH-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides; iv. –CH(CH3)–(CH2) n –CH(OH)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides; v. –CH(CH3)–(CH2) n –C(O)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides; vi. –(CH2) n –CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides; vii. –(CH2) n –CH=CH-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides; viii. –(CH2) n –CH(OH)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides; and ix.–(CH2) n –C(O)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides.

[0019] Example 11: According to the method described in Example 9, Z is selected from the group consisting of: x.–CH(CH3)–(CH2) n –CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20Heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or links to another ascaridone molecule via bonds or carbon-containing linker portions; xi. –CH(CH3)–(CH2) n –CH=CH-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 Heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or links to another ascaridone molecule via bonds or carbon-containing linker portions; xii. –CH(CH3)–(CH2) n –CH(OH)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 Heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or links to another ascaridone molecule via bonds or carbon-containing linker portions; xiii. –CH(CH3)–(CH2) n –C(O)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 Heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or links to another ascaridone molecule via bonds or carbon-containing linker portions; xiv. –(CH2) n –CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 A heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linked to another ascaridone molecule via a bond or carbon-containing linker; xv. –(CH2) n –CH=CH-CON(R 3 )2, where n is an integer from 1 to 40, and each R3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 Heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or links to another ascaridone molecule via bonds or carbon-containing linker portions; xvi. –(CH2) n –CH(OH)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 Heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or links to another ascaridone molecule via a bond or carbon-containing linker; or xvii.–(CH2). n –C(O)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linked to another ascaroside molecule via a bond or carbon-containing linker.

[0020] Example 12: The method according to any one of Examples 9 to 11, wherein R a and R b Each is -H.

[0021] Example 13: The method according to any one of Examples 9 to 12, wherein Z is –CH(CH3)–(CH2). n –CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides.

[0022] Example 14: The method according to any one of Examples 1 to 13, wherein one or more ascarosides include ascarosides selected from the group consisting of: ascr#9, ascr#10, ascr#16, ascr#18, ascr#20, ascr#22 and ascr#24.

[0023] Example 15: The method according to any one of Examples 1 to 13, wherein the one or more ascarosides include ascr#18.

[0024] Example 16: The method according to any one of Examples 1 to 15, wherein the one or more ascaroside and the one or more phytonutrients are applied simultaneously or substantially simultaneously.

[0025] Example 17: The method according to any one of Examples 1 to 16, wherein the one or more ascaroside and the one or more phytonutrients are contained in the same composition.

[0026] Example 18: The method according to any one of Examples 1 to 15, wherein the one or more ascaroside and the one or more phytonutrients are applied sequentially (in any order).

[0027] Example 19: The method according to any one of Examples 1 to 18, wherein the combination is used as seed coating.

[0028] Example 20: A composition comprising one or more ascaroside and one or more phytonutrients.

[0029] Example 21: The composition according to Example 20, wherein the one or more ascarosides and the one or more phytonutrients are present in an effective amount.

[0030] Example 22: The composition according to Example 20 or 21, wherein the one or more phytonutrients include one or more macronutrients selected from the group consisting of nitrogen-containing nutrients, phosphorus-containing nutrients, potassium-containing nutrients, calcium-containing nutrients, magnesium-containing nutrients, sulfur-containing nutrients, and combinations thereof.

[0031] Example 23: The composition according to Example 22, wherein the macronutrient is selected from nitrogen-containing nutrients, phosphorus-containing nutrients, potassium-containing nutrients, and combinations thereof.

[0032] Example 24: The composition according to any one of Examples 20 to 23, wherein the one or more phytonutrients are in the form of a mixture of nitrogen-containing nutrients, phosphorus-containing nutrients and potassium-containing nutrients.

[0033] Example 25: The composition according to Example 22, wherein the macronutrient is selected from calcium-containing nutrients, magnesium-containing nutrients, sulfur-containing nutrients, and combinations thereof.

[0034] Example 26: The composition according to any one of Examples 20 to 25, wherein the one or more phytonutrients are in the form of manure / bird droppings, fish milk, bone meal, blood meal, bio-fertilizer or cover crop.

[0035] Example 27: The composition according to any one of Examples 20 to 26, wherein the one or more phytonutrients comprise one or more micronutrients selected from the group consisting of: boron-containing nutrients, chlorine-containing nutrients, copper-containing nutrients, iron-containing nutrients, manganese-containing nutrients, molybdenum-containing nutrients, zinc-containing nutrients, and combinations thereof.

[0036] Example 28: The composition according to any one of Examples 20 to 27, wherein the one or more phytonutrients comprise one or more macronutrients and one or more micronutrients.

[0037] Example 29: A composition according to any one of Examples 20 to 28, wherein the one or more ascarosides comprises an ascaroside having structure (I):

[0038] Where Z is the C that has been substituted in an optional manner. 3-40 Aliphatic groups, and

[0039] R a and R b Each of them is independently -H, or an optionally substituted portion of a group consisting of the following: C 1-20 aliphatic, C 1-20 Acyl group, C 1-20 Heteroaliphatic, aryl, heteroaryl, hydroxyl protecting groups, phosphorus-linked functional groups, sulfur-linked functional groups, silicon-linked functional groups, C 2-20 Carbonates (e.g., partially -C(O)OR) c C 2-20 Carbamates (e.g., partially -C(O)N(R) c )2) C 2-20 Thioesters (e.g., partially -C(S)R) c C 2-20 Thiocarbonates (e.g., partially -C(S)OR) c C 2-20 Dithiocarbonates (e.g., partially -C(S)SR) c C 1-20 Thiocarbamates (e.g., partially -C(S)N(R) c )2) The sugar moiety, peptide, polymer chain, or linker to another ascaridin molecule via a bond or carbon-containing linker, wherein R c Each occurrence is independently selected from -H, optionally substituted C. 1-12 Aliphatic, optionally substituted C 1-12 Heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, polymer chain or linkage to another ascaridin molecule via a bond or carbon-containing linker, wherein R a and Rb Together they can form an optionally substituted ring, which optionally contains one or more heteroatoms and optionally one or more unsaturated sites.

[0040] Example 30: The composition according to Example 29, wherein Z is selected from the group consisting of: i. –CH(CH3)–R 1 , where R 1 C is arbitrarily substituted 1-40 Aliphatic group; ii. –CH(CH3)–(CH2) n –CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides; iii. –CH(CH3)–(CH2) n –CH=CH-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides; iv. –CH(CH3)–(CH2) n –CH(OH)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides; v. –CH(CH3)–(CH2) n –C(O)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides; vi. –(CH2) n –CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides; vii. –(CH2) n –CH=CH-CO2R 2 , where n is an integer from 1 to 40, and R 2-H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides; viii.–(CH2) n –CH(OH)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides; and ix.–(CH2) n –C(O)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides.

[0041] Example 31: The composition according to Example 29, wherein Z is x. –CH(CH3)–(CH2) n –CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 Heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or links to another ascaridone molecule via bonds or carbon-containing linker portions; xi.–CH(CH3)–(CH2) n –CH=CH-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 Heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or links to another ascaridone molecule via bonds or carbon-containing linker portions; xii.–CH(CH3)–(CH2) n –CH(OH)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20Heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or links to another ascaridone molecule via bonds or carbon-containing linker portions; xiii.–CH(CH3)–(CH2) n –C(O)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 Heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or links to another ascaridone molecule via bonds or carbon-containing linker portions; xiv.–(CH2) n –CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 Heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or links to another ascaridone molecule via bonds or carbon-containing linker portions; xv.–(CH2) n –CH=CH-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 Heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or links to another ascaridone molecule via bonds or carbon-containing linker portions; xvi.–(CH2) n –CH(OH)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 Heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or links to another ascaridone molecule via a bond or carbon-containing linker; or xvii.–(CH2). n –C(O)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linked to another ascaroside molecule via a bond or carbon-containing linker.

[0042] Example 32: The composition according to any one of Examples 29 to 31, wherein R a and R b Each is -H.

[0043] Example 33: The composition according to any one of Examples 29 to 32, wherein Z is –CH(CH3)–(CH2). n –CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides.

[0044] Example 34: The composition according to any one of Examples 20 to 33, wherein the one or more ascarosides comprise ascarosides selected from the group consisting of: ascr#9, ascr#10, ascr#16, ascr#18, ascr#20, ascr#22 and ascr#24.

[0045] Example 35: The composition according to any one of Examples 20 to 33, wherein the one or more ascarosides include ascr#18.

[0046] Example 36: The composition according to any one of Examples 20 to 35, wherein the composition is in liquid form.

[0047] Example 37: The composition according to Example 36, wherein the liquid form is a sprayable formulation.

[0048] Example 38: The composition according to any one of Examples 20 to 35, wherein the composition is in solid form.

[0049] Example 39: The composition according to Example 38, wherein the solid form comprises powder or granules.

[0050] Example 40: The composition according to any one of Examples 20 to 39, wherein the composition is in liquid form.

[0051] Example 41: The composition according to any one of Examples 20 to 40, wherein the composition is stable for a period of time greater than 6 months.

[0052] Example 42: A composition according to any one of Examples 20 to 41, wherein the composition further comprises one or more additional components selected from the group consisting of surfactants including emulsifiers, dispersants, foaming agents, colorants, processing aids, lubricants, fillers, reinforcing agents, flame retardants, light stabilizers, ultraviolet radiation absorbers, climate stabilizers, plasticizers, release agents, fragrances, heat-insulating additives (e.g., silica), crosslinking agents, antioxidants, defoamers, buffers, pH adjusters, compatibilizers, drift control additives, expanders / adhesives, tackifiers, plant penetrants, safeners, spreading agents, and wetting agents.

[0053] These and other features, aspects, and advantages of this disclosure will become apparent from the following detailed description and accompanying drawings. The invention includes any combination of two, three, four, or more of the above embodiments, and any combination of any two, three, four, or more features or elements shown in this disclosure, whether or not such features or elements are explicitly combined in the detailed description herein. Unless the context clearly indicates otherwise, this disclosure is intended to be read holistically such that any separable features or elements of the disclosed invention in any aspect and embodiment thereof should be considered as intended to be composable. Detailed Implementation

[0054] This disclosure provides compositions and methods relating to the use of one or more ascaroside and one or more phytonutrients. As used herein, the term "ascaroside" includes ascaroside, its derivatives, analogs, or combinations thereof, as will be described in further detail herein. Ascaroside can be used with any phytonutrient, which will also be described in further detail herein.

[0055] The one or more ascarosides and the one or more nutrients can be used in the same composition, or the one or more ascarosides and the one or more nutrients can be applied simultaneously or sequentially (e.g., in separate formulations). If applied sequentially, these applications are close enough in time that they can work together to produce beneficial results.

[0056] As described above, the methods and compositions of the present invention comprise ascaroside. Ascaroside is a secondary metabolite produced by nematodes. Many structurally diverse ascarosides have been identified in nature, and these ascarosides are considered to function as an evolutionarily conserved chemical language used by nematodes to control many aspects of their development.

[0057] Ascaroside is a derivative of ascaroside, a dideoxysugar lacking hydroxyl groups at positions 3 and 6. Ascaroside has the general structure shown in Formula I:

[0058]

[0059] (Formula I),

[0060] in:

[0061] Z represents C, which is arbitrarily substituted. 2-40 Aliphatic groups, and

[0062] R a and R b Each of them is independently -H or an optionally substituted portion of a group consisting of the following: C 1-20 aliphatic, C 1-20 Acyl group, C 1-20 Heteroaliphatic, aryl, heteroaryl, hydroxyl protecting groups, phosphorus-linked functional groups, sulfur-linked functional groups, silicon-linked functional groups, C 2-20 Carbonates (e.g., partially -C(O)OR) c C 2-20 Carbamates (e.g., partially -C(O)N(R) c )2) C 2-20 Thioesters (e.g., partially -C(S)R) c C 2-20 Thiocarbonates (e.g., partially -C(S)OR) c C 2-20 Dithiocarbonates (e.g., partially -C(S)SR) c C 1-20 Thiocarbamates (e.g., partially -C(S)N(R) c 2) The sugar moiety, peptide, polymer chain, or linker to another ascaridin molecule via a bond or carbon-containing linker.

[0063] Each R c Each occurrence is independently selected from -H, optionally substituted C. 1-12 Aliphatic, optionally substituted C 1-12 Heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, polymer chain or linkage to another ascaridin molecule via a bond or carbon-containing linker, and

[0064] Where R a and R b Together they can form an optionally substituted ring, which optionally contains one or more heteroatoms and optionally one or more unsaturated sites.

[0065] In some embodiments, Z is:

[0066] (i)–CH(CH3)–R 1 , where R 1 C is arbitrarily substituted 1-40 Aliphatic groups

[0067] (ii)–CH(CH3)–(CH2) n –CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, glycoside, amino acid, peptide, nucleotide, or linked to another ascaridone molecule via a bond or carbon-containing linker.

[0068] (iii)–CH(CH3)–(CH2) n –CH=CH-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, glycoside, amino acid, peptide, nucleotide, or linked to another ascaridone molecule via a bond or carbon-containing linker.

[0069] (iv)–CH(CH3)–(CH2) n –CH(OH)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, glycoside, amino acid, peptide, nucleotide, or linked to another ascaridone molecule via a bond or carbon-containing linker.

[0070] (v)–CH(CH3)–(CH2) n –C(O)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, glycoside, amino acid, peptide, nucleotide, or linked to another ascaridone molecule via a bond or carbon-containing linker.

[0071] (vi)–(CH2) n –CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, glycoside, amino acid, peptide, nucleotide, or linked to another ascaridone molecule via a bond or carbon-containing linker.

[0072] (vii)–(CH2) n –CH=CH-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, glycoside, amino acid, peptide, nucleotide, or linked to another ascaridone molecule via a bond or carbon-containing linker.

[0073] (viii)–(CH2) n –CH(OH)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 Heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, glycosides, amino acids, peptides, nucleotides, or linkage to another ascaridone molecule via a bond or carbon-containing linker; or

[0074] (ix)–(CH2) n –C(O)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, glycoside, amino acid, peptide, nucleotide, or linked to another ascaridone molecule via a bond or carbon-containing linker.

[0075] In some embodiments, Z is:

[0076] (x)–CH(CH3)–(CH2) n –CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker.

[0077] (xi)–CH(CH3)–(CH2) n –CH=CH-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker.

[0078] (xii)–CH(CH3)–(CH2) n –CH(OH)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker.

[0079] (xiii)–CH(CH3)–(CH2) n –C(O)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker.

[0080] (xiv)–(CH2) n –CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker.

[0081] (xv)–(CH2) n –CH=CH-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker.

[0082] (xvi)–(CH2) n –CH(OH)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker.

[0083] (xvii)–(CH2) n –C(O)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 Heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or linkages to another ascaridone molecule via bonds or carbon-containing linker portions; or

[0084] (xviii) Optionally unsaturated, optional substituted C 2-40Side chains terminate at chain ends containing functional groups of nitrogen, oxygen, or sulfur.

[0085] As defined above and described herein, in some embodiments, Z includes a nitrogen-, oxygen-, or sulfur-containing functional group. It will be understood that "oxygen-containing functional group" refers to a portion containing one or more oxygen atoms (e.g., carbonyl groups, such as esters, aldehydes, carboxylic acids, orthoesters, and ketones; ethers, hydroxyl groups, and heterocycles containing one or more oxygen atoms and / or one of the aforementioned functional groups); "nitrogen-containing functional group" refers to a portion containing one or more nitrogen atoms (e.g., amines, amides, carbamates, imines, ureas, oximes, amidines, guanidines, nitriles, azo groups, azides, and heterocycles containing one or more nitrogen atoms and / or one of the aforementioned functional groups); and "sulfur-containing functional group" refers to a portion containing one or more sulfur atoms (e.g., thioethers, sulfones, sulfonic acids, sulfoxides, thiols, thiocyanates, or disulfides).

[0086] In some embodiments, Z is optionally unsaturated, optionally substituted C. 2-40 Side chains terminate at chain ends containing oxygen-containing functional groups. In some embodiments, Z is optionally unsaturated, optionally substituted C. 2-40 Side chain, terminating at the end containing a carboxylic acid. In some embodiments, Z is optionally unsaturated, optionally substituted C. 2-40 Side chains that terminate at the aldehyde-containing chain end. In some embodiments, Z is optionally unsaturated, optionally substituted C. 2-40 Side chain, terminating at the end of the chain containing the ester. In some embodiments, Z is optionally unsaturated, optionally substituted C. 2-40 Side chain, which terminates at a point containing -CO2R 2 The chain end. In some embodiments, Z is optionally unsaturated, optionally substituted C 2-40 Side chains that terminate at a chain end containing -CO2H. In some embodiments, Z is optionally unsaturated, optionally substituted C 2-40 Side chains that terminate at a chain end containing -CO2CH3. In some embodiments, Z is optionally unsaturated, optionally substituted C 2-40 Sidechain, which terminates at a point containing -CON(R) 3 The chain end of )2. In some embodiments, Z is optionally unsaturated, optionally substituted C 2-40 Sidechain, which terminates at a point containing -N(R) 3 The chain end of )2. In some embodiments, Z is optionally unsaturated, optionally substituted C 2-40 Side chain, which terminates at the end of an ester containing a linker portion covalently attached to one or more other ascaroside molecules.

[0087] As stated above, the sucralose moiety in the provided compound can be substituted or unsubstituted (i.e., the 2 and 4 positions of the sugar can have functional groups other than -OH, or in other words, the variable R in any of the formulas herein). a and / or R b It can be omitted (-H).

[0088] As defined above and as described in this article, R a and R b Each of them is independently -H or an optionally substituted portion of a group consisting of the following: C 1-20 aliphatic, C 1-20 Acyl group, C 1-20 Heteroaliphatic, aryl, heteroaryl, hydroxyl protecting groups, phosphorus-linked functional groups, sulfur-linked functional groups, silicon-linked functional groups, C 2-20 Carbonates (e.g., partially -C(O)OR) c C 2-20 Carbamates (e.g., partially -C(O)N(R) c )2) C 2-20 Thioesters (e.g., partially -C(S)R) c C 2-20 Thiocarbonates (e.g., partially -C(S)OR) c C 2-20 Dithiocarbonates (e.g., partially -C(S)SR) c C 1-20 Thiocarbamates (e.g., partially -C(S)N(R) c )2) The sugar moiety, peptide, polymer chain or the ascaroside molecule is linked to the ascaroside molecule via a bond or carbon-containing linker.

[0089] In some embodiments, R a For -H. In some embodiments, R b For -H. In some embodiments, R a and R b They are the same. In some embodiments, R a and R b Both are -H. In some embodiments, R a and R b They are different. In some embodiments, R a It is -H, and R b Not -H. In some embodiments, R a Not -H and R b For -H. In some embodiments, R a -H and R b It is a para-hydroxybenzoic acid ester. In some embodiments, R a -H and Rb It is an indole-3-carboxylate. In some embodiments, R a -H and R b It is (E)-2-methyl-2-butenoate. In some embodiments, R a -H and R b It is a pyridine carboxylate. In some embodiments, R a -H and R b It is nicotinic acid ester. In some embodiments, R a -H and R b It is (R)-2-hydroxy-2-(4-hydroxyphenyl)ethyl)amino)-4-oxobutyrate. In some embodiments, R a -H and R b It is 4-((4-hydroxyphenylethyl)amino)-4-oxobutyrate. In some embodiments, R a It contains glycosides, amino acids, peptides, or nucleotides. In some embodiments, R b It contains glycosides, amino acids, peptides, or nucleotides. In some embodiments, R a It includes a link to a second ascaroside molecule. In some embodiments, R b It includes a link to an ascaroside molecule. In some embodiments, R a Contains sugar. In some embodiments, R b It contains sugar.

[0090] In some embodiments, R a C is arbitrarily substituted 1-20 Aliphatic. In some embodiments, R a C is arbitrarily substituted 1-6 Aliphatic. In some embodiments, R a C 1-20 Aliphatic. In some embodiments, R a C 1-6 Aliphatic. In some embodiments, R a It is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl. In some embodiments, R a C 1-20 Acyl group. In some embodiments, R a -C(O)R c In some embodiments, R a It is -C(O)H. In some embodiments, R a It is -C(O)CH3. In some embodiments, R a C is arbitrarily substituted 1-20 Aliphatic. In some embodiments, R a C is arbitrarily substituted1-6 Aliphatic. In some embodiments, R a C 1-20 Aliphatic. In some embodiments, R a C 1-6 Aliphatic. In some embodiments, R a It is a optionally substituted 3- or 8-membered saturated or partially unsaturated heterocyclic group having 1 to 3 independently selected heteroatoms chosen from nitrogen, oxygen, or sulfur. In some embodiments, R a It is an optionally substituted 8- or 12-membered saturated or partially unsaturated bicyclic heterocyclic group having 1 to 4 independently selected heteroatoms chosen from nitrogen, oxygen, or sulfur. In some embodiments, R a The aryl group is optionally substituted. In some embodiments, R a Optionally substituted phenyl. In some embodiments, R a It is phenyl. In some embodiments, R a R is an optionally substituted heteroaryl group. In some embodiments, R a It is a optionally substituted 5- to 6-membered heteroaryl group having 1 to 3 independently selected heteroatoms chosen from nitrogen, oxygen, or sulfur. In some embodiments, R a It is an optionally substituted 8- to 12-membered heteroaryl group having 1 to 4 independently selected heteroatoms chosen from nitrogen, oxygen, or sulfur. In some embodiments, R a C is arbitrarily substituted 2-20 Carbonate. In some embodiments, R a -C(O)OR c In some embodiments, R a C is arbitrarily substituted 2-20 Carbamate. In some embodiments, R a -C(O)N(R) c )2. In some embodiments, R a C is arbitrarily substituted 2-20 Thioesters. In some embodiments, R a -C(S)R c In some embodiments, R a C is arbitrarily substituted 2-20 Thiocarbonates. In some embodiments, R a -C(S)OR c In some embodiments, R a C is arbitrarily substituted 2-20 Dithiocarbonate. In some embodiments, R a -C(S)SR c In some embodiments, R a C is arbitrarily substituted 1-20Thiocarbamates. In some embodiments, R a -C(S)N(R) c )2.

[0091] In some embodiments, R a Optionally substituted hydroxyl protecting groups. Suitable hydroxyl protecting groups are well known in the art and include those described in Protecting Groups in Organic Synthesis, TWGreene and PGM Wuts, 3rd edition, John Wiley & Sons, 1999. Examples of suitable oxygen protecting groups include, but are not limited to, acetyl, benzoylbenzyl, β-methoxyethoxymethyl ether (MEM), dimethoxytriphenylmethyl (DMT), methoxymethyl ether (MOM), methoxytriphenylmethyl (MMT), p-methoxybenzyl ether (PMB), methyl thiomethyl ether, pivaloyl, tetrahydropyranyl (THP), tetrahydrofuranyl (THF), triphenylmethyl, silyl ethers (e.g., trimethylsilyl (TMS), tert-butyldimethylsilyl (TBDMS), triisopropylsilyloxymethyl (TOM), and triisopropylsilyl (TIPS) ether), methyl ethers, and ethoxyethyl ethers. In some embodiments, R a For -OR c .

[0092] In some embodiments, R a This is an optionally substituted phosphorus-linked functional group. It will be understood that, as used herein, "phosphorus-linked functional group" refers to a moiety containing one or more phosphorus atoms (e.g., phosphine, phosphate diester, phosphonic acid, phosphate ester). In some embodiments, R a This is an optionally substituted sulfur-linked functional group. It will be understood that, as used herein, "sulfur-linked functional group" refers to a moiety containing one or more sulfur atoms (e.g., thioethers, sulfones, sulfonic acids, sulfoxides, thiols, thiocyanates, or disulfides). In some embodiments, R a The silicon-linked functional group is optionally substituted. It will be understood that, as used herein, "silicon-linked functional group" refers to a portion containing one or more silicon atoms (e.g., silanol, sulfoxide, siloxane, silyl ether, silyl chloride, silyl hydride, silene, or thiophene).

[0093] In some embodiments, R a For optionally substituted sugar portions. In some embodiments, R a The peptide is optionally substituted. In some embodiments, R a For optionally substituted polymer chains. In some embodiments, R aThis is a connection to the ascaroside molecule via a bond or a carbon-containing linker. In some embodiments, R a C-type compounds containing ascaroside, optionally substituted 1-6 Aliphatic or mixed adipose.

[0094] In some embodiments, R b C is arbitrarily substituted 1-20 Aliphatic. In some embodiments, R b C is arbitrarily substituted 1-6 Aliphatic. In some embodiments, R b C 1-20 Aliphatic. In some embodiments, R b C 1-6 Aliphatic. In some embodiments, R b It is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl. In some embodiments, R b C 1-20 Acyl group. In some embodiments, R b -C(O)R c In some embodiments, R b It is -C(O)H. In some embodiments, R b It is -C(O)CH3. In some embodiments, R b C is arbitrarily substituted 1-20 Aliphatic. In some embodiments, R b C is arbitrarily substituted 1-6 Aliphatic. In some embodiments, R b C 1-20 Aliphatic. In some embodiments, R b C 1-6 Aliphatic. In some embodiments, R b It is a optionally substituted 3- or 8-membered saturated or partially unsaturated heterocyclic group having 1 to 3 independently selected heteroatoms chosen from nitrogen, oxygen, or sulfur. In some embodiments, R b It is an optionally substituted 8- or 12-membered saturated or partially unsaturated bicyclic heterocyclic group having 1 to 4 independently selected heteroatoms chosen from nitrogen, oxygen, or sulfur. In some embodiments, R b The aryl group is optionally substituted. In some embodiments, R b Optionally substituted phenyl. In some embodiments, R b It is phenyl. In some embodiments, R b R is an optionally substituted heteroaryl group. In some embodiments, R b It is a optionally substituted 5- to 6-membered heteroaryl group having 1 to 3 independently selected heteroatoms chosen from nitrogen, oxygen, or sulfur. In some embodiments, Rb It is an optionally substituted 8- to 12-membered heteroaryl group having 1 to 4 independently selected heteroatoms chosen from nitrogen, oxygen, or sulfur. In some embodiments, R b C is arbitrarily substituted 2-20 Carbonate. In some embodiments, R b -C(O)OR c In some embodiments, R b C is arbitrarily substituted 2-20 Carbamate. In some embodiments, R b -C(O)N(R) c )2. In some embodiments, R b C is arbitrarily substituted 2-20 Thioesters. In some embodiments, R b -C(S)R c In some embodiments, R b C is arbitrarily substituted 2-20 Thiocarbonates. In some embodiments, R b -C(S)OR c In some embodiments, R b C is arbitrarily substituted 2-20 Dithiocarbonate. In some embodiments, R b -C(S)SR c In some embodiments, R a C is arbitrarily substituted 1-20 Thiocarbamates. In some embodiments, R b -C(S)N(R) c )2.

[0095] In some embodiments, R b The hydroxyl protecting group is optionally substituted. In some embodiments, R b For -OR c .

[0096] In some embodiments, R b R is an optionally substituted phosphorus-linked functional group. In some embodiments, R b R is an optionally substituted sulfur-linked functional group. In some embodiments, R b These are optional silicon-linked functional groups.

[0097] In some embodiments, R b For optionally substituted sugar portions. In some embodiments, R a The peptide is optionally substituted. In some embodiments, R b For optionally substituted polymer chains. In some embodiments, Rb This is a connection to the ascaroside molecule via a bond or a carbon-containing linker. In some embodiments, R b C-type compounds containing ascaroside, optionally substituted 1-6 Aliphatic or mixed adipose.

[0098] In some embodiments, R a and R b Together they can form optionally substituted rings, which optionally contain one or more heteroatoms and optionally one or more unsaturated sites. In some embodiments, R a and R b Together, they can form optionally substituted 3- to 12-membered monocyclic or bicyclic saturated or partially unsaturated carbocyclic or heterocyclic rings having 1 to 4 independently selected heteroatoms chosen from nitrogen, oxygen, or sulfur. In some embodiments, R a and R b Together they can form 5- to 12-membered monocyclic or bicyclic aryl or heteroaryl rings having 1 to 4 independently selected heteroatoms chosen from nitrogen, oxygen or sulfur.

[0099] In some embodiments, R a -H and R b It is a para-hydroxybenzoic acid ester. In some embodiments, R a -H and R b It is an indole-3-carboxylate. In some embodiments, R a -H and R b It is (E)-2-methyl-2-butenoate. In some embodiments, R a -H and R b It is a pyridine carboxylate. In some embodiments, R a -H and R b It is nicotinic acid ester. In some embodiments, R a -H and R b It is (R)-2-hydroxy-2-(4-hydroxyphenyl)ethyl)amino)-4-oxobutyrate. In some embodiments, R a -H and R b It is 4-((4-hydroxyphenylethyl)amino)-4-oxobutyrate.

[0100] In some embodiments, R a and R b All are -H, and Z is selected from the formulas defined in (i) to (ix) above. In some embodiments, R a and R b Both are -H, and Z conforms to equation (i) above. In some embodiments, R a and R bBoth are -H, and Z conforms to equation (ii) above. In some embodiments, R a and R b Both are -H, and Z conforms to equation (iii) above. In some embodiments, R a and R b Both are -H, and Z conforms to equation (iv) above. In some embodiments, R a and R b Both are -H, and Z conforms to the above equation (v). In some embodiments, R a and R b Both are -H, and Z conforms to the above equation (vi). In some embodiments, R a and R b Both are -H, and Z conforms to the above equation (vii). In some embodiments, R a and R b Both are -H, and Z conforms to the above equation (viii). In some embodiments, R a and R b Both are -H, and Z conforms to the above equation (ix). In some embodiments, R a and R b Both are -H, and Z conforms to the above equation (x). In some embodiments, R a and R b Both are -H, and Z conforms to the above equation (xi). In some embodiments, R a and R b Both are -H, and Z conforms to the above equation (xii). In some embodiments, R a and R b Both are -H, and Z conforms to equation (xiii) above. In some embodiments, R a and R b Both are -H, and Z conforms to the above equation (xiv). In some embodiments, R a and R b Both are -H, and Z conforms to the above equation (xv). In some embodiments, R a and R b Both are -H, and Z conforms to the above equation (xvi). In some embodiments, R a and R b Both are -H, and Z satisfies the above formula (xvii).

[0101] As defined above and as described in this article, each R c Each occurrence is independently selected from -H, optionally substituted C. 1-12 Aliphatic, optionally substituted C 1-12Heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, polymer chain or linked to another ascaridin molecule via a bond or carbon-containing linker.

[0102] In some embodiments, R c Each occurrence is independently selected from -H, optionally substituted C. 1-12 Aliphatic, optionally substituted C 1-12 Heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl.

[0103] In some embodiments, R c The occurrence of is -H. In some embodiments, R c C is arbitrarily substituted 1-12 Aliphatic group. In some embodiments, R c C is arbitrarily substituted 1-6 Aliphatic group. In some embodiments, R c C is arbitrarily substituted 1-12 heteroaliphatic groups. In some embodiments, R c C is arbitrarily substituted 1-6 heteroaliphatic groups. In some embodiments, R c It is a optionally substituted 3- or 8-membered saturated or partially unsaturated heterocyclic group having 1 to 3 independently selected heteroatoms chosen from nitrogen, oxygen, or sulfur. In some embodiments, R c It is an optionally substituted 8- or 12-membered saturated or partially unsaturated bicyclic heterocyclic group having 1 to 4 independently selected heteroatoms chosen from nitrogen, oxygen, or sulfur. In some embodiments, R c Optionally substituted aryl groups. In some embodiments, R c Optionally substituted phenyl. In some embodiments, R 2 It is phenyl. In some embodiments, R c R is an optionally substituted heteroaryl group. In some embodiments, R c It is a optionally substituted 5- to 6-membered heteroaryl group having 1 to 3 independently selected heteroatoms chosen from nitrogen, oxygen, or sulfur. In some embodiments, R c It is an 8- to 12-membered heteroaryl group having 1 to 4 independently selected heteroatoms chosen from nitrogen, oxygen or sulfur, which are optionally substituted.

[0104] As defined above and as described in this article, R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20Heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, glycosides, amino acids, peptides, nucleotides, or linkage to another ascaridone molecule via a bond or carbon-containing linker. In some embodiments, R 2 -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 Heteroaliphatic groups or optionally substituted aromatic groups, optionally substituted heteroaryl groups.

[0105] In some embodiments, R 2 For -H. In some embodiments, R 2 It is a metal cation. In some embodiments, R 2 It is an organic cation (e.g., a cationic group centered on nitrogen or phosphorus). In some embodiments, R 2 C is arbitrarily substituted 1-20 Aliphatic groups. In some embodiments, R 2 C is arbitrarily substituted 1-12 Aliphatic groups. In some embodiments, R 2 C is arbitrarily substituted 1-8 Aliphatic groups. In some embodiments, R 2 C is arbitrarily substituted 1-6 Aliphatic groups. In some embodiments, R 2 Selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, and tert-butyl. In some embodiments, R 2 C is arbitrarily substituted 1-6 Aliphatic group. In some embodiments, R 2 C is arbitrarily substituted 1-20 heteroaliphatic groups. In some embodiments, R 2 C is arbitrarily substituted 1-6 heteroaliphatic groups. In some embodiments, R 2 It is a optionally substituted 3- or 8-membered saturated or partially unsaturated heterocyclic group having 1 to 3 independently selected heteroatoms chosen from nitrogen, oxygen, or sulfur. In some embodiments, R 2 It is an optionally substituted 8- or 12-membered saturated or partially unsaturated bicyclic heterocyclic group having 1 to 4 independently selected heteroatoms chosen from nitrogen, oxygen, or sulfur. In some embodiments, R 2 R is an optionally substituted aromatic group. In some embodiments, R 2 Optionally substituted phenyl. In some embodiments, R 2 It is phenyl. In some embodiments, R 2 R is an optionally substituted heteroaryl group. In some embodiments, R 2It is a optionally substituted 5- to 6-membered heteroaryl group having 1 to 3 independently selected heteroatoms chosen from nitrogen, oxygen, or sulfur. In some embodiments, R 2 It is an 8- to 12-membered heteroaryl group having 1 to 4 independently selected heteroatoms chosen from nitrogen, oxygen or sulfur, which are optionally substituted.

[0106] In some embodiments, R 2 Glycosides. It will be understood that a glycoside is a portion of a sugar that is linked to another functional group via a glycosidic bond.

[0107] In some embodiments, R 2 It is a nucleotide. In some embodiments, R 2 It is adenosine monophosphate, cytidine monophosphate, guanosine monophosphate, or uridine monophosphate. In some embodiments, R 2 It is deoxyadenosine monophosphate, deoxycytidine monophosphate, deoxyguanosine monophosphate, or deoxythymidine monophosphate.

[0108] In some embodiments, R 2 For linkage to another ascaroside molecule via a bond or carbon-containing linker. In some embodiments, R 2 C-type compounds containing ascaroside, optionally substituted 1-6 Aliphatic or mixed adipose.

[0109] In some embodiments, R 2 It contains amino acids. In some embodiments, R 2 It contains peptides.

[0110] As defined above and as described in this article, each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 Heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or linkages to another ascaridone molecule via bonds or carbon-containing linker portions. In some embodiments, each R 3 Independently selected from -H and C 1-8 Aliphatic. In some embodiments, an R 3 For -H and another R 3 Not -H. In some embodiments, R 3 None of them are -H. In some embodiments, each R 3 For -H. In some embodiments, R 3 The appearance of C is optionally substituted 1-20 Aliphatic group. In some embodiments, R 3 The appearance of C is optionally substituted 1-6 Aliphatic group. In some embodiments, R3 The appearance of C is optionally substituted 1-20 heteroaliphatic groups. In some embodiments, R 3 The appearance of C is optionally substituted 1-6 heteroaliphatic groups. In some embodiments, R 3 It is a optionally substituted 3- or 8-membered saturated or partially unsaturated heterocyclic group having 1 to 3 independently selected heteroatoms chosen from nitrogen, oxygen, or sulfur. In some embodiments, R 3 It is an optionally substituted 8- or 12-membered saturated or partially unsaturated bicyclic heterocyclic group having 1 to 4 independently selected heteroatoms chosen from nitrogen, oxygen, or sulfur. In some embodiments, R 3 The presence of is optionally a substituted aryl group. In some embodiments, R 3 Optionally substituted phenyl. In some embodiments, R 3 It is phenyl. In some embodiments, R 3 R is an optionally substituted heteroaryl group. In some embodiments, R 3 It is a optionally substituted 5- to 6-membered heteroaryl group having 1 to 3 independently selected heteroatoms chosen from nitrogen, oxygen, or sulfur. In some embodiments, R 3 It is an 8- to 12-membered heteroaryl group having 1 to 4 independently selected heteroatoms chosen from nitrogen, oxygen or sulfur, which are optionally substituted.

[0111] In some embodiments, at least one R 3 -H. In some embodiments, two R 3 All groups are -H. In some embodiments, at least one R 3 C is arbitrarily substituted 1-20 Aliphatic groups. In some embodiments, two R groups... 3 The group is an optionally substituted C 1-20 Aliphatic groups, which may be the same or different. In some embodiments, at least one R 3 C is arbitrarily substituted 1-12 Aliphatic group. In some embodiments, at least one R 3 C is arbitrarily substituted 1-8 Aliphatic group. In some embodiments, at least one R 3 C is arbitrarily substituted 1-6 Aliphatic group. In some embodiments, at least one R 3 The solvent is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, and tert-butyl. In some embodiments, at least one R 3 It is -CH2CH2OH. In some embodiments, at least one R 3 -CH2CH2OR 2, where R 2 It is as defined in the genus and subgenus herein. In some embodiments, at least one R 3 Optionally substituted aromatic groups. In some embodiments, at least one R 3 Contains glycosides. In some embodiments, at least one R 3 Contains amino acids. In some embodiments, at least one R 3 At least one R 3 Contains peptides. In some embodiments, at least one R 3 It contains nucleotides.

[0112] In some embodiments, ascaroside is selected from the group consisting of:

[0113]

[0114] Where x is an integer from 1 to 22, and R a R b and R 2 Each of them is as defined above and in this text as a genus and subgenus.

[0115] In some embodiments, ascaroside is selected from the group consisting of:

[0116]

[0117] Where x and R a and R b Each of them is as defined above and in this text as a genus and subgenus.

[0118] In some embodiments, ascaroside is selected from the group consisting of:

[0119]

[0120] Where y is an integer from 1 to 20, and R a R b and R 2 Each of them is as defined above and in this text as a genus and subgenus.

[0121] In some embodiments, ascaroside is selected from the group consisting of:

[0122]

[0123] Where y and R a and R b Each of them is as defined above and in this text as a genus and subgenus.

[0124] In some embodiments, ascaroside is selected from the group consisting of:

[0125]

[0126] Where x and R 2 Each of them is as defined above and in this text as a genus and subgenus.

[0127] In some embodiments, ascaroside is selected from the group consisting of:

[0128]

[0129] Where x is defined as above and as in this article as genus and subgenus.

[0130] In some embodiments, ascaroside is selected from the group consisting of:

[0131]

[0132] Where y and R 2 Each of them is as defined above and in this text as a genus and subgenus.

[0133] In some embodiments, ascaroside is selected from the group consisting of:

[0134]

[0135] Where y is defined as above and as in this article as genus and subgenus.

[0136] In some embodiments, ascaroside is selected from the group consisting of:

[0137]

[0138] Where x and R a R b and R 3 Each of them is as defined above and in this text as a genus and subgenus.

[0139] In some embodiments, ascaroside is selected from the group consisting of:

[0140]

[0141] Where x and R 3 Each of them is as defined above and in this text as a genus and subgenus.

[0142] In some embodiments, ascaroside is selected from the group consisting of:

[0143]

[0144] Where y and R a R b and R 2Each of them is as defined above and in this text as a genus and subgenus.

[0145] In some embodiments, ascaroside is selected from the group consisting of:

[0146]

[0147] Where y and R 3 Each of them is as defined above and in this text as a genus and subgenus.

[0148] In the embodiments, the ascaroside available in the context of this disclosure has a universal structure (I), where Z is –CH(CH3)–(CH2). n –CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides.

[0149] In the embodiments, the ascaroside available in the context of this disclosure has a universal structure (I), where Z is –CH(CH3)–(CH2). n –CH=CH-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides.

[0150] Specific ascarosides available in the context of this disclosure include, but are not limited to, ascr#7 and ascr#18.

[0151]

[0152] In some embodiments, the ascaroside used in the provided methods and compositions is selected from the group consisting of: ASCII#9, ASCII#12, ASCII#14, ASCII#1, ASCII#10, ASCII#16, ASCII#18, ASCII#20, ASCII#22, ASCII#24, ASCII#26, ASCII#28, ASCII#30, ASCII#32, ASCII#34, and ASCII#36. In some embodiments, the ascaroside used in the provided methods is selected from the group consisting of: ASCII#10, ASCII#16, ASCII#18, ASCII#20, ASCII#22, and ASCII#24. In some embodiments, the ascaroside used in the provided methods is selected from the group consisting of: ASCII#9, ASCII#14, ASCII#10, and ASCII#18.

[0153] In some embodiments, the ascaroside used in the provided methods and compositions is selected from the group consisting of: oscr#5, oscr#9, oscr#12, oscr#1, oscr#14, oscr#10, oscr#16, oscr#18, oscr#20, oscr#22, oscr#24, oscr#26, oscr#28, oscr#30, oscr#32, oscr#34, and oscr#36. In some embodiments, the ascaroside used in the provided methods is selected from the group consisting of: oscr#10, oscr#16, oscr#18, oscr#20, and oscr#22. In some embodiments, the ascaroside used in the provided method is selected from the group consisting of: bhas#5, oscr#9, oscr#12, oscr#1, oscr#14, oscr#10, oscr#16, oscr#18, oscr#20, oscr#22, oscr#24, oscr#26, oscr#28, oscr#30, oscr#32, oscr#34, and oscr#36. In some embodiments, the ascaroside used in the provided method is selected from the group consisting of: oscr#10, oscr#16, oscr#18, oscr#20, and oscr#22.

[0154] In some embodiments, the ascaroside used in the provided methods and compositions is selected from the group consisting of: bhas#9, bhas#10, bhas#16, bhas#18, bhas#22, bhas#24, bhas#26, bhas#28, bhas#30, bhas#32, bhas#34, bhas#36, bhas#38, bhas#40 and bhas#42.

[0155] In some embodiments, the ascaroside used in the provided methods and compositions is selected from the group consisting of: bhos#10, bhos#16, bhos#18, bhos#22, bhos#24, bhos#26, bhos#28, bhos#30, bhos#32, bhos#34, bhos#36, bhos#38, bhos#40, and bhos#42.

[0156] In some embodiments, the ascaroside used in the provided methods and compositions is selected from the group consisting of: ascr#18, oscr#16, oscr#17, oscr#15, bhas#18, bhos#16, glas#18, dhas#18, ibha#18, ibho#16, icas#18, icos#15, icos#16, and any combination of two or more of these. In some embodiments, the ascaroside used in the provided methods and compositions is ascr#18. In some embodiments, the ascaroside used in the provided methods and compositions is oscr#16.

[0157] Ascaroside can be obtained from natural sources (e.g., nematodes) or prepared synthetically. Ascaroside can be prepared synthetically, for example by converting 1-O-substituted rhamnose to 1-O-substituted ascaroside. Exemplary methods for preparing ascaroside include: providing 1-O-substituted rhamnose as a starting material; forming a monosulfonate ester on the 3-OH group of the starting material; and treating the monosulfonate ester with a hydride source to form the 1-O-substituted ascaroside. In some embodiments, the formation of the monosulfonate ester is carried out on a substrate without a hydroxyl protecting group at the 2 or 4 position of the rhamnose starting material. In some embodiments, such methods include contacting the starting material with a sulfonating agent (i.e., a sulfonyl halide, sulfonic anhydride, or a similar agent) in the presence of a Lewis acid. Specific details regarding the synthesis of 1-O-substituted ascaroside can be found in International Publication No. WO 2022 / 024067, which is incorporated herein by reference.

[0158] As noted, according to this disclosure, ascaroside is used in combination with phytonutrients. As used herein, the term "phytonutrient" encompasses compounds containing elements essential or beneficial to plant growth and / or development. "Essential" elements are generally considered to be elements required for the life cycle of a plant species. "Beneficial" elements may not meet the necessity criterion but may contribute to plant growth and development or to the quality attributes of the plant or its harvested products. Phytonutrients include elements identified as having a defined metabolic function in plants, as well as elements demonstrated to have significant benefits for plant productivity, crop quality, resource use efficiency, stress tolerance, and / or resistance to pests and diseases.

[0159] In some embodiments, the phytonutrients are mineral phytonutrients. The compounds and compositions suitable for use in the various embodiments of this disclosure may comprise one or more of the following: major nutrients (nitrogen (N), phosphorus (P), and / or potassium (K), commonly referred to as "NPK nutrients"); minor nutrients (calcium (Ca), magnesium (Mg), and sulfur (S)); and / or trace nutrients (including, but not limited to, boron (B), chlorine (Cl), copper (Cu), iron (Fe), manganese (Mn), molybdenum (Mo), and zinc (Zn)). These nutrient classifications (major, minor, and trace) are primarily related to the required amount of each nutrient; major nutrients are required in relatively large amounts, minor nutrients in smaller amounts, and trace nutrients in smaller amounts. Major and minor nutrients are sometimes referred to as "macronutrients," and trace nutrients are sometimes referred to as "micronutrients."

[0160] While not intended to be theoretically limited, nitrogen (N) is generally understood to be a key element in plant / vegetable growth, and in particular to promote good stem growth. Compounds according to this disclosure that can provide N and thus act as phytonutrients include, but are not limited to, ammonium sulfate, ammonium nitrate, and urea.

[0161] While not intended to be theoretically limited, phosphorus (P) is generally understood to enhance plant root systems, seed production, disease and insect resistance, and improve flowering and the texture and flavor of edible plants and vegetables. Sources of phosphorus include, but are not limited to, superphosphate (made from phosphate and sulfate). Grain-fed animal manure is another common source of phosphorus.

[0162] While not intended to be theoretically limited, potassium (K) is generally understood to increase plant vigor and disease resistance, contribute to the formation and movement of starch, sugars, and oils in plants, improve flowering and fruit / fruit quality, and is also important for root and seed production. Sources of potassium include, but are not limited to, potassium chloride and potassium sulfate, as well as wood ash and banana peels.

[0163] In some embodiments, these three major macronutrients (P, N, and K) can be applied via a nutrient-rich composition comprising two or three of these major nutrients. Such nutrient-rich compositions include, but are not limited to, manure or guano, fish milk, bone meal, blood meal, bio-fertilizers, and cover crops.

[0164] The NPK ratio of such nutrient-rich compositions can vary. In some embodiments, a nutrient mixture with equivalent N, P, and K values ​​is used (e.g., a formulation with a 6-6-6 NPK ratio). In some embodiments, a nutrient mixture with a relatively high N ratio is used (e.g., a formulation with a 20-6-6 NPK ratio). Nutrient mixtures with other NPK ratios may be used; there are no particular limitations on the NPK ratios associated with this disclosure. As other examples, a good formulation for promoting rooting and post-transplant care may be a formulation with a 6-20-20 NPK ratio, and a good formulation for supporting and protecting flower development may be a formulation with a 6-20-6 NPK ratio. Formulas for grasses may have high “N” values, such as a 30-0-0 NPK ratio. Generally, any nutrient mixture with any NPK ratio suitable for a given plant at a given stage of plant growth under given conditions is used in conjunction with the ascaroside provided herein.

[0165] While not intended to be theoretically limited, calcium (Ca) is generally understood to enhance and strengthen plant tissues and help neutralize acidity within the plant (acting as a detoxifier by neutralizing organic acids) and in the surrounding soil (especially when lime is applied, increasing crop yield). Calcium activates multiple enzyme systems in protein synthesis and carbohydrate translocation. It is involved in the formation and plasticity of plant cell wall membranes. In peanuts, calcium is essential for seed production. Sources of calcium include, but are not limited to, gypsum.

[0166] While not intended to be theoretically limited, magnesium (Mg) is generally understood to help increase phosphorus uptake and promote chlorophyll production, thus providing plants with a healthy green color and facilitating CO2 absorption. Magnesium is also a cofactor in several enzyme reactions that activate phosphorylation and is essential for stabilizing ribosome particles and nucleic acid structures. Furthermore, magnesium plays a role in aiding the movement of sugars within plants. Sources of magnesium include, but are not limited to, garden lime (e.g., dolomite lime with high magnesium levels or calcified lime with high calcium content).

[0167] Although not intended to be theoretically limited, sulfur (S) is generally understood to actively participate in the metabolism of biotin and thiamine, as well as coenzyme A, and to contribute to seed production, chlorophyll formation, root nodule formation in legumes, and the stability of protein structures.

[0168] Although not intended to be theoretically limited, boron (B) is generally understood to promote root growth and is essential for pollen germination and pollen tube growth. Boron is also associated with lignin synthesis, the activity of certain enzymes, seed and cell wall formation, and sugar transport within plants.

[0169] Although not intended to be theoretically limited, chlorine (Cl) is generally understood to be essential for photosynthesis (because it participates in the release of oxygen). Chlorine increases cell osmotic pressure and the water content of plant tissues.

[0170] Although not intended to be theoretically limited, copper (Cu) is generally understood to be essential in several plant enzyme systems involved in photosynthesis. It may play a role in the synthesis and / or stability of chlorophyll and other plant pigments.

[0171] Although not intended to be theoretically limited, iron (Fe) is generally understood to be essential in the heme enzyme system of plant metabolism, which affects photosynthesis and respiration. It is thought to be crucial for the synthesis and maintenance of chlorophyll in plants and is considered to be closely related to protein metabolism.

[0172] Although not intended to be theoretically limited, manganese (Mn) is generally understood to function primarily as part of plant enzyme systems, activating a variety of metabolic functions and also participating in the redox processes of photosynthesis. It has been further demonstrated to activate indoleacetic acid oxidase, which then oxidizes indoleacetic acid in plants.

[0173] Although not intended to be theoretically limited, molybdenum (Mb) is generally understood to be an important component of two major enzymes required for normal nitrogen assimilation in plants, and is required by some soil microorganisms for nitrogen fixation in soil.

[0174] While not intended to be theoretically limited, zinc (Zn) is generally understood to be essential for the synthesis of tryptophan, which in turn is essential for the formation of indoleacetic acid in plants and is also a necessary component of several metalloenzymes in plants. Zn can also activate carbonic anhydrase and plays a role in RNA and protein synthesis in plants.

[0175] It is worth noting that while this application focuses on the combined application of ascaroside with one or more phytonutrients, ascaroside can alternatively (or additionally) be applied with one or more general soil conditioners that can, for example, enhance the ability of plants to absorb nutrients. Such general soil conditioners include, but are not limited to, compost, mulch, worm castings, wood ash, lime, and other natural additives that enhance the use and availability of nutrients.

[0176] The methods provided herein involve applying an effective amount of one or more ascarosides and an effective amount of one or more phytonutrients to seeds, plants, plant leaves, or the soil in which the plants grow. According to this disclosure, in some embodiments, one or more phytonutrients and one or more ascarosides may be applied at one or more relevant times during phytonutrient application (e.g., when a nutrient deficiency is suspected / confirmed for a given plant or crop). Advantageously, ascarosides can provide a long-lasting effect against pathogen damage to crops and can therefore be conveniently applied together with one or more nutrients at various stages. Thus, in some embodiments provided herein, these components may be applied at a single time point corresponding to the time point required to ensure sufficient phytonutrient balance in order to provide both nutrients and pathogen protection to the plant.

[0177] The application of one or more nutrients and one or more ascaridins can be pre-emergence or post-emergence. Preferred application methods depend on the usual or optimal application time of a particular nutrient or nutrient. Typically, nutrients are added to the plant during its growth period and / or flowering period. In some embodiments, the timing of application of one or more nutrients and one or more ascaridins according to this disclosure can be crop-specific. Sometimes, some of these nutrients are required at a higher value than others. It is noteworthy that phytonutrients (which may be the same or, more commonly, different) can be applied more than once during the growth period; one or more ascaridins can be applied together with related phytonutrients in one or more of these nutrient applications. For example, in some embodiments, one or more ascaridins are applied together with the first application of a given phytonutrient (e.g., at the seedling stage). In some embodiments, one or more ascaridins are applied together with the final application of a given phytonutrient.

[0178] In some embodiments, this disclosure provides a method for applying a macronutrient in combination with one or more ascaridosin. In some embodiments, this disclosure provides a method for applying a micronutrient in combination with one or more ascaridosin. In some embodiments, this disclosure provides a method for applying a nitrogenous phytonutrient in combination with one or more ascaridosin. In some embodiments, this disclosure provides a method for applying a potassium-containing phytonutrient in combination with one or more ascaridosin. In some embodiments, this disclosure provides a method for applying a phosphorus-containing phytonutrient in combination with one or more ascaridosin. In some embodiments, this disclosure provides a method for applying a nitrogenous phytonutrient and a phosphorus-containing phytonutrient in combination with one or more ascaridosin. In some embodiments, this disclosure provides a method for applying a phosphorus-containing phytonutrient and a potassium-containing phytonutrient in combination with one or more ascaridosin. In some embodiments, this disclosure provides a method for applying a nitrogenous phytonutrient, a phosphorus-containing phytonutrient, and a potassium-containing phytonutrient in combination with one or more ascaridosin. In some embodiments, this disclosure provides a method for applying a calcium-containing phytonutrient in combination with one or more ascaridosin. In some embodiments, this disclosure provides a method for applying a magnesium-containing phytonutrient in combination with one or more ascarosides. In some embodiments, this disclosure provides a method for applying a sulfur-containing phytonutrient in combination with one or more ascarosides.

[0179] In some embodiments, this disclosure provides a method for applying a boron-containing phytonutrient in combination with one or more ascaridosin glycosides. In some embodiments, this disclosure provides a method for applying a chlorine-containing phytonutrient in combination with one or more ascaridosin glycosides. In some embodiments, this disclosure provides a method for applying a copper-containing phytonutrient in combination with one or more ascaridosin glycosides. In some embodiments, this disclosure provides a method for applying an iron-containing phytonutrient in combination with one or more ascaridosin glycosides. In some embodiments, this disclosure provides a method for applying a manganese-containing phytonutrient in combination with one or more ascaridosin glycosides. In some embodiments, this disclosure provides a method for applying a molybdenum-containing phytonutrient in combination with one or more ascaridosin glycosides. In some embodiments, this disclosure provides a method for applying a zinc-containing phytonutrient in combination with one or more ascaridosin glycosides.

[0180] In some embodiments, the methods provided herein may include monitoring plants and / or the soil around growing plants to assess nutrient levels and, based on the results of such monitoring, applying appropriate combinations of one or more nutrients with one or more ascarosides.

[0181] In some embodiments, this monitoring involves simply assessing the plant's appearance, as nutrient deficiencies or imbalances can often be identified based on a few general signs. For example, nitrogen deficiency may cause affected plants to have pale green and / or yellow leaves (usually appearing first on older leaves and then on younger leaves as the deficiency worsens); slower, stunted growth; and, in some plants, the shedding of older leaves. Phosphorus deficiency may cause overall stunted growth and, in severe cases, abnormally dark green leaves (older growth) and / or dead areas on the leaves (usually affecting older leaves first, then younger leaves), as well as affected fruits and stems. Purple or reddish hues may be observed on the leaves of deficient corn plants. Phosphorus deficiency may further result in a lack of flowering / flower drop and / or a scorched leaf tip appearance. Potassium deficiency may cause yellowing of the leaf margins of older leaves in affected plants. Potassium-deficient plants grow slowly, have poor root development, and weak stems, and therefore often loiter. Wilting old trees may also be a sign of potassium deficiency. Calcium deficiency can lead to poor root growth, and in severe cases, the growing point may die. Roots deficient in calcium typically turn black and rot; symptoms may appear at the growing points of young leaves and buds, and the plant may exhibit gum-like leaf tips. Magnesium deficiency can cause leaves to turn yellow, bronze, or red, while the veins remain green (usually first appearing on the lower, older leaves). Calcium deficiency can cause flower tip rot (in fruits such as tomatoes).

[0182] In some embodiments, such monitoring includes assessing the soil content of various nutrients via soil testing. It is noteworthy that soil nitrogen testing is generally inaccurate due to the high mobility of nitrogen in soil. However, soil testing for other nutrients can provide information about nutrients that are advantageously applied to plants grown in such soil to optimize plant growth and corresponding characteristics. This analysis can provide insights into the location and timing of nutrient application. Suitable tests may include, for example, extracting and processing soil samples and analyzing the resulting extracts via one or more analytical methods, including but not limited to laser scanning confocal microscopy, mass spectrometry, digestion, combustion, and other methods. In some embodiments, such monitoring includes foliar testing for various nutrients.

[0183] The antipathogenic activity of ascaridin provides additional benefits to the methods and compositions provided herein. Advantageously and conveniently, by applying one or more ascaridins in combination with one or more phytonutrients, the step of applying antimicrobial agents (e.g., fungicides, antibiotics, antivirals, or anti-helmintics) can be omitted (e.g., later in the plant growth cycle) due to the durable effect provided by the one or more ascaridins. For example, while fungicides and antibacterial agents are typically applied at later points in crop growth when such pathogens are present, this disclosure provides methods and compositions for applying ascaridins at very early points in time (i.e., the points at which one or more nutrients are conventionally applied to crops), and can confer resistance to pathogens in crops treated in this way. In some embodiments, ascaridins surprisingly exhibit durable effects, such as reducing or preventing damage caused by fungi, bacteria, viruses, and molds for periods exceeding 3 days, 5 days, 1 week, 2 weeks, 1 month, 2 months, or 3 months after application.

[0184] Co-application of one or more nutrients and one or more ascaridins at a single point in time (e.g., including but not limited to early in the season) can also provide growers with significant economic advantages and enhance the sustainability of crop production. Co-application of ascaridins with one or more nutrients can avoid the need for separate fungicide or antimicrobial treatments later in the season. This saves fuel and labor and may avoid the need for additional toxic pathogen control products, as ascaridin treatment can act as a preventative control to enhance crop tolerance to a wide range of pathogens. Another or alternative benefit of combining ascaridins with one or more nutrients is the control of early-season plant pathogens such as fungi, bacteria, viruses, and nematodes. Co-application of ascaridins with one or more nutrients can avoid the need for separate early-season disease control applications (e.g., fungicides, antimicrobials, or nematicides), thus saving fuel and labor, and may avoid the need for additional toxic pathogen control products, as ascaridin treatment can act as a preventative control to enhance crop tolerance to a variety of pathogens.

[0185] In some embodiments, this disclosure provides blends or compositions of one or more phytonutrients and one or more ascaridosin. In some embodiments, this disclosure provides blends of one or more phytonutrients and one or more ascaridosin, characterized in that the blend provides nutrients to the plant and also protects the plant from pathogens. In some embodiments, this disclosure provides blends or compositions of one or more phytonutrients and one or more ascaridosin, wherein treatment with said blend increases yield by at least about 5%, at least about 10%, at least about 15%, at least about 20%, at least about 25%, at least about 30%, at least about 35%, at least about 40%, at least about 50%, at least about 60%, at least about 75%, or at least about 90% compared to plants treated with the nutrients alone. In some embodiments, this disclosure provides blends or compositions of one or more phytonutrients and one or more ascarosides, wherein treatment with the blend increases yield by between 0 and about 5%, between about 5% and about 10%, between about 10% and about 15%, between about 15% and about 20%, between about 20% and about 25%, between about 25% and about 30%, between 30% and about 35%, between about 35% and about 40%, between about 40% and about 50%, between about 50% and about 60%, between about 60% and about 75%, or between about 75% and about 90%, relative to plants treated with the nutrient alone. In some embodiments, this disclosure provides blends or compositions of one or more phytonutrients and one or more ascarosides, wherein treatment with the blend increases yield by about 5%, about 10%, about 15%, about 20%, about 25%, about 30%, about 35%, about 40%, about 50%, about 60%, about 75%, or about 90% compared to plants treated with the nutrients alone.

[0186] The compounds described herein (i.e., one or more phytonutrients and one or more ascaridins) may be provided as a single formulation or agricultural composition or as separate formulations or agricultural compositions. Alternatively, these components may be applied separately. When one or more ascaridins and one or more phytonutrients are applied separately, one or more ascaridins may be applied before or after the application of the phytonutrients. Typically, when applied separately, the components are applied together at close points in time, for example substantially simultaneously or within about a few minutes or hours (including within about 5 minutes, about 10 minutes, about 30 minutes, about one hour, about 2 hours, about 3 hours, about 4 hours, about 6 hours, about 7 hours, about 8 hours, about 24 hours, or about 2 days).

[0187] In some embodiments, co-application may involve combining one or more ascarosides and one or more phytonutrients before application to the plants (e.g., just before application). One or more ascarosides and one or more phytonutrients may be mixed in the field; for example, one or more ascarosides may be added to a fully formulated tank mixture containing one or more phytonutrients.

[0188] In other embodiments, the components to be applied together can be combined at a point in time prior to application. In such embodiments, an agricultural formulation is prepared comprising a combination of one or more ascarosides and one or more phytonutrients with one or more inert ingredients. Advantageously, in such combinations, one or more ascarosides and one or more phytonutrients are compatible with each other, and the resulting formulation can exhibit stability over long periods of time (e.g., about one week or longer, about one month or longer, about two months or longer, about three months or longer, about four months or longer, about five months or longer, or about six months or longer).

[0189] One or more ascarosides and one or more phytonutrients can be formulated together in a compound preparation. As mentioned above, the preparation or method may include other active ingredients and / or plant or plant product processing compounds. Furthermore, some compositions may leave residues because they are not easily washed off the leaves during rain, thus protecting the plant during and after rain.

[0190] In some embodiments, this disclosure provides a blend of one or more phytonutrients and one or more ascarosides, wherein the weight ratio of the one or more phytonutrients to ascarosides is greater than 100:1, greater than 500:1, or greater than 1000:1. In some embodiments, this disclosure provides blends of phytonutrients and ascaroside, wherein the weight ratio of one or more phytonutrients to ascaroside is greater than 1500:1, greater than 2000:1, greater than 3000:1, greater than 5000:1, greater than 7500:1, greater than 10,000:1, greater than 15,000:1, greater than 20,000:1, greater than 30,000:1, greater than 50,000:1, greater than 100,000:1, greater than 500,000:1, greater than 1,000,000:1, greater than 2,000,000:1, greater than 5,000,000:1, or greater than 10,000,000:1.

[0191] In some embodiments, the provided compositions comprise formulations intended for application to crops such that they apply to the leaves of the crops a combination of one or more ascaridins and an effective amount of one or more phytonutrients at a rate of about 1 mg to about 1,000 mg per acre. In some embodiments, such compositions are formulated for application such that they deliver ascaridins at a rate of 1 to 10 mg per acre, ascaridins at a rate of 5 to 25 mg per acre, ascaridins at a rate of 25 to 100 mg per acre, ascaridins at a rate of about 100 to 500 mg per acre, or ascaridins at a rate of 500 to 1,000 mg per acre.

[0192] In some embodiments, the provided compositions are formulated such that they are applied to the leaves of crops to deliver a combination of one or more ascaridins at a rate of about 1 mg to about 1000 mg per acre and at least 2 oz per acre of nitrogen phytonutrient. In some such embodiments, the compositions are formulated for application such that they deliver ascaridins at a rate of 1 to 10 mg per acre, ascaridins at a rate of 5 to 25 mg per acre, ascaridins at a rate of 25 to 100 mg per acre, ascaridins at a rate of about 100 to 500 mg per acre, or ascaridins at a rate of 500 to 1000 mg per acre. In some such embodiments, the compositions are formulated for application such that they deliver at least 4 oz of nitrogen per acre, at least 8 oz of nitrogen per acre, at least 1 pound of nitrogen per acre, at least 2 pounds of nitrogen per acre, at least 5 pounds of nitrogen per acre, or at least 10 pounds of nitrogen per acre.

[0193] In some embodiments, the provided compositions are formulated such that they are applied to the leaves of crops to deliver a combination of one or more ascaridins at a rate of about 1 mg to about 1000 mg per acre and at least 2 oz per acre of potassium phytonutrient. In some such embodiments, the compositions are formulated for application such that they deliver ascaridins at a rate of 1 to 10 mg per acre, ascaridins at a rate of 5 to 25 mg per acre, ascaridins at a rate of 25 to 100 mg per acre, ascaridins at a rate of about 100 to 500 mg per acre, or ascaridins at a rate of 500 to 1000 mg per acre. In some such embodiments, the compositions are formulated for application such that they deliver at least 4 oz per acre of potassium, at least 8 oz per acre of potassium, at least 1 pound per acre of potassium, at least 2 pounds per acre of potassium, at least 5 pounds per acre of potassium, or at least 10 pounds per acre of potassium.

[0194] In some embodiments, the provided compositions are formulated such that they are applied to the leaves of crops to deliver a combination of one or more ascaridones and a phosphorus phytonutrient at an amount between about 1 mg and about 1000 mg per acre and at least 1 oz per acre. In some such embodiments, the compositions are formulated for application such that they deliver ascaridone at a rate of 1 to 10 mg per acre, ascaridone at a rate of 5 to 25 mg per acre, ascaridone at a rate of 25 to 100 mg per acre, ascaridone at a rate of about 100 to 500 mg per acre, or ascaridone at a rate of 500 to 1000 mg per acre. In some such embodiments, the compositions are formulated for application such that they deliver at least 2 oz of phosphorus per acre, at least 4 oz of phosphorus per acre, at least 8 oz of phosphorus per acre, at least 1 pound of phosphorus per acre, at least 2 pounds of phosphorus per acre, at least 5 pounds of phosphorus per acre, or at least 10 pounds of phosphorus per acre.

[0195] In some embodiments, the formulation delivers one or more ascarosides in any combination of nitrogen, sulfur, or phosphorus in any combination of the amounts described above or herein. In some embodiments, the formulation delivers one or more ascarosides in any combination of nitrogen, potassium, or phosphorus in any combination of the amounts described above or herein.

[0196] In some embodiments, the provided compositions are formulated such that they are applied to the leaves of crops to deliver a combination of one or more ascaridones and an effective amount of sulfur, calcium, or magnesium phytonutrients at a concentration of about 1 mg to about 1000 mg per acre. In some such embodiments, the compositions are formulated for application such that they deliver ascaridone at a concentration of 1 to 10 mg per acre, ascaridone at a concentration of 5 to 25 mg per acre, ascaridone at a concentration of 25 to 100 mg per acre, ascaridone at a concentration of about 100 to 500 mg per acre, or ascaridone at a concentration of 500 to 1000 mg per acre. In some such embodiments, the compositions are formulated for application such that they deliver at least 0.1 oz of sulfur per acre, at least 0.5 oz of sulfur per acre, at least 1 oz of sulfur per acre, at least 2 oz of sulfur per acre, at least 4 oz of sulfur per acre, at least 8 oz of sulfur per acre, at least 1 pound of sulfur per acre, at least 2 pounds of sulfur per acre, at least 5 pounds of sulfur per acre, or at least 10 pounds of sulfur per acre. In some such embodiments, the compositions are formulated for application such that they deliver at least 0.1 oz of calcium per acre, at least 0.5 oz of calcium per acre, at least 1 oz of calcium per acre, at least 2 oz of calcium per acre, at least 4 oz of calcium per acre, at least 8 oz of calcium per acre, or at least 1 pound of calcium per acre. In some such embodiments, the compositions are formulated for application such that they deliver at least 0.1 oz of magnesium per acre, at least 0.5 oz of magnesium per acre, at least 1 oz of magnesium per acre, at least 2 oz of magnesium per acre, at least 4 oz of magnesium per acre, at least 8 oz of magnesium per acre, or at least 1 pound of magnesium per acre. In some embodiments, such formulations deliver one or more ascarosides in any combination of sulfur, calcium, and magnesium in any of the above amounts.

[0197] In some embodiments, the provided compositions are formulated such that they are applied to the leaves of crops to deliver a combination of one or more ascaridins and an effective amount of one or more plant micronutrients at a rate of about 1 mg to about 1000 mg per acre. In some such embodiments, the compositions are formulated for application such that they deliver ascaridins at a rate of 1 to 10 mg per acre, ascaridins at a rate of 5 to 25 mg per acre, ascaridins at a rate of 25 to 100 mg per acre, ascaridins at a rate of about 100 to 500 mg per acre, or ascaridins at a rate of 500 to 1000 mg per acre. In some such embodiments, the compositions are formulated for application such that they also deliver an effective amount of zinc in addition to ascaridins. In some embodiments, such compositions are formulated to deliver zinc at a rate of at least 0.1 oz, at least 0.5 oz, at least 1 oz, at least 2 oz, at least 4 oz, or at least 8 oz per acre. In some such embodiments, the compositions are formulated for application such that they also deliver an effective amount of iron in addition to ascaridins. In some embodiments, such compositions are formulated to deliver iron at a rate of at least 0.1 oz, at least 0.5 oz, at least 1 oz, at least 2 oz, at least 4 oz, or at least 8 oz per acre. In some such embodiments, the compositions are formulated for application such that they also deliver an effective amount of manganese in addition to ascaroside. In some embodiments, such compositions are formulated to deliver manganese at a rate of at least 0.1 oz, at least 0.5 oz, at least 1 oz, at least 2 oz, at least 4 oz, or at least 8 oz per acre. In some such embodiments, the compositions are formulated for application such that they also deliver an effective amount of boron in addition to ascaroside. In some embodiments, such compositions are formulated to deliver boron at a rate of at least 0.1 oz, at least 0.5 oz, at least 1 oz, at least 2 oz, at least 4 oz, or at least 8 oz per acre. In some such embodiments, the compositions are formulated for application such that they also deliver an effective amount of silicon in addition to ascaroside. In some embodiments, such compositions are formulated to deliver silicon at a rate of at least 0.1 oz, at least 0.5 oz, at least 1 oz, at least 2 oz, at least 4 oz, or at least 8 oz per acre. In some such embodiments, the compositions are formulated for application such that they also deliver an effective amount of copper in addition to ascaroside. In some embodiments, such compositions are formulated to deliver copper at a rate of at least 0.1 oz, at least 0.5 oz, at least 1 oz, at least 2 oz, at least 4 oz, or at least 8 oz per acre. In some such embodiments, the compositions are formulated for application such that they also deliver an effective amount of molybdenum in addition to ascaroside. In some embodiments, such compositions are formulated to deliver molybdenum at a rate of at least 0.1 oz, at least 0.5 oz, at least 1 oz, at least 2 oz, or at least 4 oz, or at least 8 oz per acre.In some such embodiments, the compositions are formulated for application such that they deliver an effective amount of nickel in addition to ascaroside. In some embodiments, such compositions are formulated to deliver nickel at a rate of at least 0.1 oz, at least 0.5 oz, at least 1 oz, at least 2 oz, at least 4 oz, or at least 8 oz per acre. In some embodiments, such formulations deliver one or more ascarosides in any combination of two or more of zinc, iron, manganese, boron, silicon, molybdenum, copper, and nickel in any of the amounts described above.

[0198] The formulation or composition can be formulated according to conventional methods in the art and can be a liquid or dry composition. Dry compositions include powders, etc. The composition can be used as a liquid concentrate, a ready-to-use (RTU) liquid spray, a powder, or a solid, depending on the user's needs. The selected formulation will depend on the intended use of the product. When in use, the composition can be applied directly to the plant.

[0199] Generally, formulations will include at least one ascaridin as described herein, or at least one ascaridin and one or more phytonutrients, and one or more agriculturally acceptable adjuvants (also referred to herein as "agriculturally suitable adjuvants"). Agriculturally suitable adjuvants are used to enhance the effectiveness of the compounds described herein and include, but are not limited to, surfactants, emulsifiers, oils, salts, etc. Adjuvants may be added to formulations or, alternatively, may be added separately when applied to crops. In some embodiments, wetting agents, emulsifiers, spreading agents, etc., may be used in formulations. Formulations include concentrated forms in which the active agents of the invention (compounds as described herein) are present at a concentration of 0.001% to 98.0%, with the remainder being a physiologically acceptable carrier. Such formulations (especially those containing less than 50% of the compounds of the invention) can sometimes be used directly, but these formulations may also be diluted with other physiologically acceptable carriers to form more diluted treatment formulations. These subsequent formulations may contain lower concentrations of the compounds described herein, from 0.001% to 0.1%.

[0200] The formulation may additionally contain "adjuvant surfactants" to enhance the deposition, wetting, and penetration of the compound on target crops and organisms. These "adjuvant surfactants" may optionally be used as components of the formulation or as canister mixtures. The amount of adjuvant surfactant is typically 0.01 to 1.0% by volume, preferably 0.05 to 0.5% by volume, based on the water spray volume. Suitable adjuvant surfactants include, but are not limited to, ethoxylated nonylphenol, ethoxylated synthetic or natural alcohols, esters or sulfosuccinic acid salts, ethoxylated silicones, ethoxylated fatty amines, blends of surfactants with mineral or vegetable oils, crop oil concentrates (mineral oil (85%) + emulsifier (15%)); nonylphenol ethoxylates; benzyl cocoyl alkyl dimethyl quaternary ammonium salts; blends of petroleum hydrocarbons, alkyl esters, organic acids and anionic surfactants; C9-Cu alkyl polysaccharides; phosphorylated alcohol ethoxylates; natural primary alcohols (C12 to C16) ethoxylates; di-sec-butylphenol EO-PO block copolymers; polysiloxane-methyl caps; nonylphenol ethoxylates + urea ammonium nitrate; emulsified methylated seed oils; tridecanol (synthetic) ethoxylates (8EO); animal fat amine ethoxylates (15EO); PEG (400) dioleate-99. Formulations may also include oil-in-water emulsions.

[0201] In the case of wettable powder formulations, "surfactant" typically constitutes about 0.5% to about 10% of the wettable powder. Suitable "surfactants" for wettable powders include sulfonated lignin, condensed naphthalene sulfonates, naphthalene sulfonates, alkylbenzene sulfonates, alkyl sulfonates, or nonionic surfactants such as ethylene oxide adducts of alkylphenols or mixtures thereof.

[0202] Representative organic solvents that can be used to prepare emulsifiable concentrates of one or more of the disclosed ascarosides and / or one or more phytonutrients are aromatic liquids, such as xylene, propylbenzene fractions; or mixed naphthalene fractions, mineral oils, substituted aromatic organic liquids such as dioctyl phthalate; kerosene; dialkylamides of various fatty acids, especially dimethylamides of fatty glycols and diol derivatives, such as n-butyl ether, ethyl ether or methyl ether of diethylene glycol, methyl ether of triethylene glycol, amides of simple carboxylic acids, such as dimethylformamide and dimethylacetamide, petroleum fractions or hydrocarbons such as mineral oils, aromatic solvents, paraffin oils, etc.; terpene solvents, rosin derivatives, aliphatic ketones such as cyclohexanone, complex aliphatic and aromatic alcohols such as 2-ethoxyethanol, vegetable oils such as soybean oil, rapeseed oil, olive oil, castor oil, sunflower oil, coconut oil, corn oil, cottonseed oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil, tung oil, etc.; esters of the above vegetable oils; etc. Mixtures of two or more organic liquids can also be used to prepare emulsifiable concentrates. Organic liquids include xylene and propylbenzene fractions, with xylene being the preferred choice in some cases. Surfactant dispersants are commonly used in liquid formulations, and their dosage ranges from 0.1 to 20% by weight, based on the combined weight of the dispersant with one or more compounds.

[0203] "Emulsifiers" used for emulsifiable concentrates are typically mixtures of ionic and / or nonionic surfactants, such as those mentioned herein or their equivalents. Examples of nonionic emulsifiers that can be used to prepare emulsifiable concentrates include polyalkylene glycol ethers and condensation products of alkyl and aryl phenols, fatty alcohols, fatty amines, or fatty acids with ethylene oxide or propylene oxide, such as ethoxylated alkylphenols and carboxylic acid esters solubilized with polyols or polyoxyethylenes. Cationic emulsifiers include quaternary ammonium salts and fatty amine salts. Anionic emulsifiers include oil-soluble salts of alkyl aryl sulfonic acids (e.g., calcium), oil-soluble salts, or suitable salts of sulfated and phosphorylated polyethylene glycol ethers.

[0204] Powders containing one or more ascarosides and / or one or more phytonutrients can be prepared by tightly mixing one or more powdered compounds with a suitable powdered agricultural carrier (such as, for example, kaolin, ground volcanic rock, etc.). Based on the total weight of the powder, the powder may suitably contain about 1 to about 10% by weight of the compound.

[0205] Wettable powders can be formed into clumps or compacted to form water-dispersible particles. These particles comprise a mixture of compounds, an inert carrier suitable for particle application, and a surfactant. The concentration of the compound is typically between about 0.1% by weight and about 90% by weight. "Inert carriers suitable for particle application" are typically wax stone, talc, chalk, gypsum, bleaching clay, bentonite, palygorskite, starch, casein, gluten, montmorillonite clay, diatomaceous earth, purified silicates, etc. In such operations, the finely chopped carrier and surfactant are typically blended with one or more compounds and ground.

[0206] An "aqueous suspension" can be prepared in which one or more ascarosides and / or one or more phytonutrients are dispersed in an aqueous medium at concentrations typically ranging from about 5% to about 50% by weight. The suspension is prepared by finely grinding the compound and vigorously mixing it into a medium of water, surfactants, and dispersants. Inert components such as inorganic salts and synthetic or natural gums can also be used to increase the density and / or viscosity of the aqueous medium as needed.

[0207] definition

[0208] To facilitate understanding of this disclosure, certain terms are defined below. Further definitions for these and other terms are set forth throughout the specification. In this application, unless clearly apparent from the context, the term "an" or "a" may be understood to mean "at least one / a kind".

[0209] As used in this application, the term "or" can be understood to mean "and / or". In this application, the terms "comprising" and "including" can be understood to cover the listed components or steps, whether presented alone or together with one or more other components or steps. As used in this application, the term "comprise" and variations thereof (such as "comprising" and "comprises") are not intended to exclude other additives, components, wholes, or steps.

[0210] About, approximately: As used herein, the terms “about” and “approximately” are used equivalently. Unless otherwise stated, the terms “about” and “approximately” are to be understood as allowing for standard variations as would be understood by one of ordinary skill in the art. Where the scope provided herein includes endpoints. Any numbers used in this application with or without “about” are intended to cover any normal fluctuations as understood by one of ordinary skill in the relevant art. Unless otherwise stated, the above terms refer to within 25% of a given value. In some embodiments, the terms “about” or “approximately” refer to a range of values ​​that are 20%, 19%, 18%, 17%, 16%, 15%, 14%, 13%, 12%, 11%, 10%, 9%, 8%, 7%, 6%, 5%, 4%, 3%, 2%, 1% or less of the reference value in either direction, unless otherwise stated or obvious from the context (unless the number would exceed 100% of a possible value).

[0211] The definitions of specific functional groups and chemical terms are described in more detail below. For the purposes of this invention, chemical elements are identified according to the Periodic Table of the Elements, CAS edition, Handbook of Chemistry and Physics, 75th edition, inner cover, and specific functional groups are generally defined as described herein. Furthermore, general principles of organic chemistry, as well as specific functional groups and reactivity, are described in the following references: Organic Chemistry, Thomas Sorrell, University Science Books, Sausalito, 1999; Smith and March March's Advanced Organic Chemistry, 5th edition, John Wiley & Sons, Inc., New York, 2001; Larock, Comprehensive Organic Transformations, VCH Publishers, Inc., New York, 1989; Carruthers, Some Modern Methods of Organic Synthesis, 3rd edition, Cambridge University Press, Cambridge, 1987; the entire contents of each reference are incorporated herein by reference.

[0212] Some of the compounds provided herein may include one or more asymmetric centers and therefore may exist in a variety of stereoisomeric forms, such as enantiomers and / or diastereomers. Thus, the compounds and compositions thereof of the present invention may be in the form of individual enantiomers, diastereomers, or geometric isomers, or may be in the form of mixtures of stereoisomers. In some embodiments, the compounds described herein are enantiomerically pure compounds. In some other embodiments, mixtures of enantiomers or diastereomers are provided.

[0213] Furthermore, unless otherwise indicated, some compounds described herein may have one or more double bonds that can exist as Z or E isomers. Compounds may be provided as single isomers substantially free of other isomers, and alternatively as mixtures of various isomers, such as racemic mixtures of enantiomers.

[0214] As used herein, the term "isomer" includes any and all geometric and stereoisomers. For example, "isomer" includes cis- and trans-isomers, E- and Z-isomers, R- and S-enantiomers, diastereomers, (D)- and (L)-isomers, racemic mixtures thereof, and other mixtures thereof, all of which fall within the scope of this disclosure. For example, in some embodiments, the compound may be provided substantially free of one or more corresponding stereoisomers and may also be referred to as "stereochemically enriched".

[0215] When a particular enantiomer is preferred, in some embodiments it may be provided substantially free of the opposite enantiomer and may also be referred to as “optically enriched.” As used herein, “optically enriched” means that the compound consists of a significantly larger proportion of one enantiomer. In some embodiments, the compound consists of at least about 90% enantiomers by weight. In some embodiments, the compound consists of at least about 95%, 97%, 98%, 99%, 99.5%, 99.7%, 99.8%, or 99.9% enantiomers by weight. In some embodiments, the enantiomer excess of the provided compound is at least about 90%, 95%, 97%, 98%, 99%, 99.5%, 99.7%, 99.8%, or 99.9%. In some embodiments, the enantiomers may be isolated from a racemic mixture or prepared by any method known to those skilled in the art, including chiral high-performance liquid chromatography (HPLC) and the formation and crystallization of chiral salts. See, for example, Jacques et al., Enantiomers, Racemates and Resolutions (Wiley Interscience, New York, 1981); Wilen, SH et al., Tetrahedron 33:2725 (1977); Eliel, ELStereochemistry of Carbon Compounds (McGraw–Hill, New York, 1962); Wilen, SH Tables of Resolving Agents and Optical Resolutions, p. 268 (edited by EL Eliel, Univ. of Notre Dame Press, Notre Dame, IN 1972).

[0216] As used herein, the terms “halo” and “halogen” refer to atoms selected from fluorine (fluorinated, -F), chlorine (chlorinated, -Cl), bromine (brominated, -Br), and iodine (iodinated, -I).

[0217] As used herein, the term "aliphatic" or "aliphatic group" means a hydrocarbon moiety that can be linear (i.e., unbranched), branched, or cyclic (including fused, bridged, and spirofused polycyclic rings) and can be fully saturated or may contain one or more unsaturated units but is not aromatic. Unless otherwise stated, an aliphatic group contains 1 to 30 carbon atoms. In some embodiments, the aliphatic group contains 1 to 12 carbon atoms. In some embodiments, the aliphatic group contains 1 to 8 carbon atoms. In some embodiments, the aliphatic group contains 1 to 6 carbon atoms. In some embodiments, the aliphatic group contains 1 to 5 carbon atoms; in some embodiments, the aliphatic group contains 1 to 4 carbon atoms; in still other embodiments, the aliphatic group contains 1 to 3 carbon atoms; and in still other embodiments, the aliphatic group contains 1 to 2 carbon atoms. Suitable aliphatic groups include, but are not limited to, linear or branched alkyl, alkenyl, and alkynyl groups and their hybrids, such as (cycloalkyl)alkyl, (cycloalkenyl)alkyl, or (cycloalkyl)alkenyl.

[0218] As used herein, the term "heteroaliphatic" or "heteroaliphatic group" refers to an aliphatic group in which one or more carbon or hydrogen atoms are replaced by heteroatoms (e.g., oxygen, nitrogen, sulfur, phosphorus, boron, etc.). In some embodiments, the heteroaliphatic group is a heterocyclic group.

[0219] As used in this article, the term "unsaturated" means that a portion of the material has one or more double or triple bonds.

[0220] As used herein, the term "alkyl" refers to a saturated straight-chain or branched hydrocarbon group derived by removing a single hydrogen atom from an aliphatic portion containing one to six carbon atoms. Unless otherwise stated, an alkyl group contains 1 to 12 carbon atoms. In some embodiments, the alkyl group contains 1 to 8 carbon atoms. In some embodiments, the alkyl group contains 1 to 6 carbon atoms. In some embodiments, the alkyl group contains 1 to 5 carbon atoms; in some embodiments, the alkyl group contains 1 to 4 carbon atoms; in still other embodiments, the alkyl group contains 1 to 3 carbon atoms; and in still other embodiments, the alkyl group contains 1 to 2 carbon atoms. Examples of alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, sec-pentyl, isopentyl, tert-butyl, n-pentyl, neopentyl, n-hexyl, sec-hexyl, n-heptyl, n-octyl, n-decyl, n-undecyl, dodecyl, etc.

[0221] As used herein, the term "alkenyl" refers to a monovalent group derived by removing a single hydrogen atom from a straight-chain or branched aliphatic moiety having at least one carbon-carbon double bond. Unless otherwise stated, an alkenyl group contains 2 to 12 carbon atoms. In some embodiments, the alkenyl group contains 2 to 8 carbon atoms. In some embodiments, the alkenyl group contains 2 to 6 carbon atoms. In some embodiments, the alkenyl group contains 2 to 5 carbon atoms; in some embodiments, the alkenyl group contains 2 to 4 carbon atoms; in still other embodiments, the alkenyl group contains 2 to 3 carbon atoms; and in still other embodiments, the alkenyl group contains 2 carbon atoms. Alkenyl groups include, for example, vinyl, propenyl, butenyl, 1-methyl-2-buten-1-yl, etc.

[0222] The term "aryl," used alone or as part of a larger part such as in "aralkyl," "arylalkoxy," or "aryloxyalkyl," refers to a monocyclic or polycyclic system having a total of five to 20 ring members, wherein at least one ring in the system is aromatic and wherein each ring in the system contains three to twelve ring members. The term "aryl" may be used interchangeably with the term "aryl ring." In some embodiments, "aryl" refers to an aromatic ring system including, but not limited to, phenyl, biphenyl, naphthyl, anthracene, etc., which may have one or more substituents. As used herein, the term "aryl" also includes groups within its scope where the aromatic ring is fused to one or more additional rings, such as benzofuranyl, indanyl, phthalimide, naphthimide, phenanthridine, or tetrahydronaphthyl.

[0223] The terms "heteroaryl" and "heteroary-" used alone or as part of a larger portion, such as "heteroarylalkyl" or "heteroarylalkoxy," refer to groups having 5 to 10 ring atoms, preferably 5, 6, or 9 ring atoms; groups sharing 6, 10, or 14 π electrons in a cyclic array; and groups having one to five heteroatoms in addition to a carbon atom. The term "heteroatom" refers to nitrogen, oxygen, or sulfur, and includes any oxidized form of nitrogen or sulfur, and any quaternized form of basic nitrogen. Heteroaryl groups include, but are not limited to, thienyl, furanyl, pyrroleyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, pyrazinyl, indoleazinyl, purine, naphridinyl, and pteridinyl. As used herein, the terms “heteroaryl” and “heteroary-” also include groups fused to one or more aryl, alicyclic, or heterocyclic rings, wherein the group or connecting point is located on the heteroaryl ring. Non-limiting examples include indolyl, isoindolyl, benzothiopheneyl, benzofuranyl, dibenzofuranyl, indazoleyl, benzimidazolyl, phenthiazolyl, quinolinyl, isoquinolinyl, cenolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, 4H-quinazinyl, carbazolyl, acridineyl, phenazinyl, phenothiazinyl, phenotoxazinyl, tetrahydroquinolinyl, tetrahydroisoquinolinyl, and pyrido[2,3–b]–1,4–oxazin–3(4H)–one. Heteroaryl groups can be monocyclic, bicyclic, bridged bicyclic, or spirocyclic. The term "heteroaryl" may be used interchangeably with the terms "heteroaryl ring," "heteroaryl group," or "heteroaromatic," any of which includes optionally substituted rings. The term "heteroarylalkyl" refers to an alkyl group substituted with a heteroaryl group, wherein the alkyl and heteroaryl portions are independently optionally substituted. The term "heteroarylenyl" refers to a divalent heteroaryl group (e.g., pyridinylenyl).

[0224] As used herein, the terms “heterocycle,” “heterocyclic group,” “heterocyclic group,” and “heterocyclic ring” are used interchangeably and refer to a stable 5- to 7-membered monocyclic or 7- to 10-membered bicyclic heterocyclic portion that is saturated or partially unsaturated and has one or more, preferably one to four, heteroatoms as defined above, in addition to a carbon atom. When referring to the ring atom of the heterocycle, the term “nitrogen” includes substituted nitrogen. As an example, in a saturated or partially unsaturated ring having 0 to 3 heteroatoms selected from oxygen, sulfur, or nitrogen, nitrogen can be N (as in 3,4-dihydro-2H-pyrrole), NH (as in pyrrolidinyl), or +NR (as in N-substituted pyrrolidinyl).

[0225] Heterocycles can be attached to their side groups at any heteroatom or carbon atom to produce a stable structure, and any ring atom can optionally be substituted. Examples of such saturated or partially unsaturated heterocyclic groups include, but are not limited to, tetrahydrofuranyl, tetrahydrothiophenyl, pyrrolyl, piperidinyl, pyrrololinyl, tetrahydroquinolinyl, tetrahydroisoquinolinyl, decahydroquinolinyl, oxazolidinyl, piperazine, dioxalyl, dioxopentyl, diazazyl, oxonitrile, thioazazyl, morpholinyl, and quininecycloyl. The terms “heterocycle,” “heterocyclic group,” “heterocyclic ring,” “heterocyclic moiety,” and “heterocyclic group” are used interchangeably herein and also include groups fused with one or more aryl, heteroaryl, or alicyclic rings, such as dihydroindolyl, 3H-indolyl, benzodihydropyranyl, phenanthridine, or tetrahydroquinolinyl. In some embodiments, the heterocycle may be a 5- to 12-membered bicyclic, bridged bicyclic, or spirocyclic. The heterocycle may contain one or more oxo (=O) or thio (=S) substituents. The term "heterocyclic alkyl" refers to an alkyl group substituted with a heterocyclic group, wherein the alkyl and heterocyclic portions are optionally substituted independently.

[0226] As used herein, the term "partially unsaturated" refers to a ring moiety containing at least one double or triple bond. The term "partially unsaturated" is intended to cover rings having multiple unsaturated sites, but not to include aryl or heteroaryl moiety as defined herein.

[0227] As described herein, compounds provided herein may contain an "optionally substituted" moiety. Generally, the term "substituted," whether or not preceded by the term "optionally," means that one or more hydrogen atoms of the specified moiety are replaced by suitable substituents. Unless otherwise indicated, the "optionally substituted" group may have suitable substituents at each substituted position of the group, and the substituents at each position may be the same or different when more than one position in any given structure is substituted by more than one substituent selected from the specified group. The contemplated combinations of substituents are preferably those that result in the formation of stable or chemically viable compounds. The term "stable" as used herein means that the compound remains substantially unchanged when subjected to conditions that allow it to be generated, detected, and, in some embodiments, recovered, purified, and used for one or more purposes disclosed herein.

[0228] The suitable monovalent substituent on the substituted carbon atom of the "optionally substituted" group is independently a halogen; –(CH2) 0–4 R°;–(CH2) 0–4 OR°;-O-(CH2) 0-4 C(O)OR°;–(CH2) 0–4 CH(OR°)2;–(CH2) 0–4 SR°;–(CH2)0– 4Ph, which can be substituted via R°; –(CH2) 0–4 O(CH2) 0–1 Ph, which can be substituted by R°; –CH=CHPh, which can be substituted by R°; –NO2; -CN; –N3; –(CH2) 0–4 N(R°)2;–(CH2) 0–4 N(R°)C(O)R°; –N(R°)C(S)R°; –(CH2) 0-4 N(R°)C(O)NR°2; –N(R°)C(S)NR°2; –(CH2) 0–4 N(R°)C(O)OR°; -N(R°)N(R°)C(O)R°; –N(R°)N(R°)C(O)NR°2; –N(R°)N(R°)C(O)OR°; –(CH2) 0–4 C(O)R°;-C(S)R°;–(CH2) 0–4 C(O)OR°;–(CH2) 0–4 C(O)N(R°)2;–(CH2) 0–4 C(O)SR°;–(CH2) 0–4 C(O)OSiR°3;–(CH2) 0–4 OC(O)R°;–OC(O)(CH2) 0–4 SR–, SC(S)SR°; –(CH2) 0–4 SC(O)R°;–(CH2) 0–4 C(O)NR°2; -C(S)NR°2; –C(S)SR°; –SC(S)SR°, –(CH2) 0–4 OC(O)NR°2; –C(O)N(OR°)R°; –C(O)C(O)R°; –C(O)CH2C(O)R°; –C(NOR°)R°; –(CH2) 0–4 SSR°;–(CH2) 0– 4S(O)2R°;–(CH2) 0–4 S(O)₂OR°;-(CH₂) 0–4 OS(O)2R°; –S(O)2NR°2; –(CH2) 0–4 S(O)R°; –N(R°)S(O)2NR°2; –N(R°)S(O)2R°; –N(OR°)R°; –C(NH)NR°2; –P(O)2R°; –P(O)R°2; –OP(O)R°2; –OP(O)(OR°)2; SiR°3; –(C 1–4 (linear or branched alkylene)O–N(R°)2; or –(C 1–4(straight-chain or branched alkylene)C(O)O–N(R°)2, wherein each R° can be substituted as defined below and is independently hydrogen, C 1-8 Aliphatic, –CH2Ph, –O(CH2) 0–1 Ph or a 5- to 6-membered saturated, partially unsaturated, or aryl ring having 0 to 4 independent heteroatoms selected from nitrogen, oxygen, or sulfur; or, in addition to the above definitions, two independently occurring R° together with one or more intermediate atoms to form a 3- to 12-membered saturated, partially saturated, or aryl monocyclic or polycyclic ring having 0 to 4 independent heteroatoms selected from nitrogen, oxygen, or sulfur, which may be substituted as defined below.

[0229] The appropriate monovalent substituent of R° is independently a halogen, –(CH2), along with its intermediate atom. 0–2 R –(halogenated R) ), –(CH2) 0–2 OH, –(CH2) 0–2 OR –(CH2) 0–2 CH(OR )2;-O(halogenated R –CN, –N3, –(CH2) 0–2 C(O)R –(CH2) 0–2 C(O)OH, –(CH2) 0–2 C(O)OR -(CH2) 0-4 C(O)N(R°)2;–(CH2) 0–2 SR –(CH2) 0–2 SH, –(CH2) 0–2 NH2、–(CH2) 0–2 NHR -(CH2) 0-2 NR 2, –NO2, –SiR 3. –OSiR 3. –C(O)SR 、–(C 1–4 (straight-chain or branched alkylene)C(O)OR Or –SSR , where each R It is either unsubstituted or, in the case of the prefix "halogenated", substituted with only one or more halogens, and independently selected from C. 1–4 Aliphatic, -CH2Ph, –O(CH2) 0–1Ph or a 5- to 6-membered saturated, partially unsaturated, or aryl ring having 0 to 4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. Suitable divalent substituents on the saturated carbon atom of R° include =O and =S.

[0230] Suitable divalent substituents on the saturated carbon atom of the "optionally substituted" group include the following: =O, =S, =NNR. * 2、=NNHC(O)R * =NNHC(O)OR * =NNHS(O)2R * =NR * =NOR * 、 –O(C(R) * 2)) 2–3 O – or –S(C(R) * 2)) 2– 3S–, where R appears independently each time * Selected from hydrogen, and C that can be substituted as defined below. 1–6 Aliphatic or unsubstituted 5- to 6-membered saturated, partially unsaturated, or aryl rings having 0 to 4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. Suitable divalent substituents bonded to the ortho-substituted carbon of the "optionally substituted" group include: –O(CR * 2) 2–3 O–, where each independently occurring R * Selected from hydrogen, C can be substituted as defined below. 1–6 Aliphatic, or having 0 to 4 unsubstituted 5 to 6 saturated, partially unsaturated or aryl rings independently selected from nitrogen, oxygen or sulfur.

[0231] R * Suitable substituents on aliphatic groups include halogens, -R -(halogenated R) –OH, –OR –O (halogenated R) ), –CN, –C(O)OH, –C(O)OR –NH2, –NHR –NR 2 or –NO2, where each R It is either unsubstituted or, in the case of the prefix "halogenated", substituted with only one or more halogens, and is independently C. 1–4 Aliphatic, –CH2Ph, –O(CH2) 0–1 Ph or a 5- to 6-membered saturated, partially unsaturated, or aryl ring having 0 to 4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0232] Suitable substituents on the substituted nitrogen of the "optionally substituted" group include –R † –NR † 2. –C(O)R † –C(O)OR † –C(O)C(O)R † –C(O)CH2C(O)R † –S(O)2R † -S(O)2NR † 2. –C(S)NR † 2. –C(NH)NR † 2 or –N(R) † )S(O)2R † ; where each R † Independently, hydrogen can be substituted C as defined below. 1-6 Aliphatic, unsubstituted -OPh, or an unsubstituted 5- to 6-membered saturated, partially unsaturated, or aryl ring having 0-4 independently selected heteroatoms chosen from nitrogen, oxygen, or sulfur; or, in addition to the above definitions, two independently occurring R... † Together with its intermediate atom, it forms an unsubstituted 3 to 12-membered saturated, partially unsaturated, or aryl monocyclic or bicyclic ring with 0 to 4 independent heteroatoms selected from nitrogen, oxygen, or sulfur.

[0233] R † Suitable substituents on the aliphatic group can be halogens, -R –(halogenated R) –OH, –OR –O (halogenated R) ), –CN, –C(O)OH, –C(O)OR –NH2, –NHR –NR 2 or -NO2, where each R It is either unsubstituted or, in the case of the prefix "halogenated", substituted with only one or more halogens, and is independently C. 1–4 Aliphatic, –CH2Ph, –O(CH2) 0–1 Ph or a 5- to 6-membered saturated, partially unsaturated, or aryl ring having 0 to 4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0234] As used in this article, the term “substantially” refers to a qualitative condition that exhibits all or nearly all of the scope or degree of the intended characteristics or properties.

[0235] Sometimes, a convention is used to name ascarosides with a few letters prefixed followed by a hash symbol (#) and a number (e.g., ascr#18). This convention is used in scientific literature, and those skilled in the art will understand that each such name relates to a specific chemical structure of known composition and will readily understand the structure of the molecule referred to using this naming convention. Unless otherwise indicated, all compound identifiers in this format used herein conform to the definitions described in the Small Molecule Identifiers Database for Caenorhabditis elegans (SMID-DB) maintained on the World Wide Web smid-db.org.

[0236] Example

[0237] Example 1: Micronutrient test of zinc ascaridin in soybeans

[0238] A trial was conducted to evaluate the efficacy of foliar application of a combination of ascaroside OSCR#16 and zinc. The trial was carried out in a 10-acre commercial soybean field in the eastern United States, divided into two zones of approximately 5 acres each. The crop was planted and maintained using typical practices for the area, at approximately growth stages V5 and R2 / R3. Half of the field was treated with a foliar spray consisting of a 4 oz / acre composition containing 0.04 wt% ascaroside OSCR#16 and 4.0 wt% soluble zinc (as zinc sulfate), diluted with sufficient water to achieve good crop coverage (corresponding to approximately 50 mg of ascaroside and 0.2 oz of zinc per acre).

[0239] Fields were regularly observed to assess differences in plant health and vigor between treated and untreated areas. After crop maturity, the treated and untreated areas were harvested separately. The fields treated with the zinc ascaroside composition were significantly healthier during the growing season, and soybean plants in the treated areas retained their leaves later in the growing season compared to plants in the untreated areas. At harvest, the treated areas produced a yield of 58.8 Bu / ac, while the untreated fields produced a yield of 48.5 Bu / ac, representing a 21% increase in yield corresponding to the application of the ascaroside composition of this invention.

[0240] Example 2: Ascaroside / Multinutrient Test in Soybeans

[0241] The experiment was conducted according to the protocol of Example 1, except that the composition was applied at 20 oz per acre and contained 0.003% oscr#16 combined with a multinutrient composition (Awaken® from Loveland Agri Products) containing 20% ​​nitrogen, 21% potassium, 0.02% boron, 0.19% copper, 0.19% iron, 0.19% manganese, 0.0007% molybdenum and 3.36% zinc.

[0242] Example 3: Ascaroside / Boron Test in Soybeans

[0243] The experiment was conducted according to the scheme of Example 1, except that the applied composition contained a composition containing 2% boron applied at a rate of 0.005% oscr#16 and 32 oz per acre.

[0244] Example 4: Ascaroside / Zinc Test in Soybeans

[0245] The experiment was conducted according to the scheme of Example 1, except that the applied composition contained ascaroside ascr#18 instead of oscr#16.

[0246] Examples 5, 6, and 7: Experiments on ascaroside nutrients in maize

[0247] The experiments were conducted according to the schemes in Examples 1 to 4, except that the composition was applied to corn instead of soybeans.

[0248] Examples 8, 9, and 10: Experiments on ascaroside nutrients in rice

[0249] The experiments were conducted according to the schemes of Examples 1 to 4, except that the compositions were applied to rice instead of soybeans, and the amount of ascaroside in each composition was reduced to 1 / 10 of the amount in Examples 1 to 4.

[0250] Examples 11, 12, and 13: Experiments on ascaroside nutrients in wheat

[0251] The experiments were conducted according to the schemes of Examples 1 to 4, except that the composition was applied to wheat instead of soybeans.

[0252] Example 14: Repeat the above experiment, but change the identity of the ascaroside to evaluate the activity of other ascarosides relative to oscr#16 and ascr#18.

[0253] The compounds, compositions, and methods of this application are intended to cover variations and adaptations developed using information from the embodiments described in this disclosure. Those skilled in the art can adjust or modify the methods and processes described in this specification.

[0254] It will be understood that the use of headings in this disclosure is for the reader's convenience. The presence and / or placement of headings are not intended to limit the scope of the subject matter described herein. Unless otherwise stated, embodiments located in one part of this application are applicable, individually or in combination, to other embodiments throughout the application.

[0255] Throughout this specification, where a composition, compound, or product is described as having, including, or containing specific components, or where a process or method is described as having, including, or containing specific steps, it is contemplated that the articles, apparatus, and systems of this application are also substantially composed of, or consist of, the said components, and that the processes and methods according to this application are also substantially composed of, or consist of, the said process steps.

[0256] It should be understood that the order of steps or the order in which an action is performed is irrelevant as long as the method remains operational. Furthermore, two or more steps or actions can be performed simultaneously.

[0257] All publications and patent applications mentioned in this specification are intended to be of the skill of a person skilled in the art to which this invention pertains. All publications and patent applications are incorporated herein by reference as if each individual publication or patent application were specifically and individually indicated to be incorporated by reference.

[0258] Although the invention has been described in detail by way of illustrations and examples for clarity, it will be apparent that certain changes and modifications may be made within the scope of the appended claims.

Claims

1. A method for providing nutrients to plants and protecting them against pathogens, the method comprising contacting the plant, plant parts, or soil surrounding the plant with an effective amount of a combination of agents comprising one or more ascarosides and one or more phytonutrients.

2. A method for providing nutrients to plants and protection against pathogens, the method comprising applying ascaroside to a plant, a plant part, or the soil surrounding the plant or plant part, wherein the plant, plant part, or the soil surrounding the plant or plant part is receiving or has received nutrients (e.g., via application to the plant, plant part, or the soil surrounding the plant or plant part).

3. A method for providing nutrients to plants and protection against pathogens, the method comprising applying nutrients to a plant, a plant part, or the soil surrounding the plant or plant part, wherein the plant, plant part, or the soil surrounding the plant or plant part is receiving or has been receiving ascaroside (e.g., via application to the plant, plant part, or the soil surrounding the plant or plant part).

4. The method according to claim 1, wherein the one or more phytonutrients include one or more macronutrients selected from the group consisting of nitrogen-containing nutrients, phosphorus-containing nutrients, potassium-containing nutrients, calcium-containing nutrients, magnesium-containing nutrients, sulfur-containing nutrients, and combinations thereof.

5. The method according to claim 1, wherein the one or more phytonutrients comprise one or more micronutrients selected from the group consisting of: boron-containing nutrients, chlorine-containing nutrients, copper-containing nutrients, iron-containing nutrients, manganese-containing nutrients, molybdenum-containing nutrients, zinc-containing nutrients, and combinations thereof.

6. The method according to claim 1, wherein the one or more phytonutrients comprise one or more macronutrients and one or more micronutrients.

7. The method according to any one of claims 1 to 6, wherein the one or more ascarosides comprises ascaroside having structure (I): in: Z represents C, which is arbitrarily substituted. 3-40 Aliphatic groups, and R a and R b Each of them is independently -H or an optionally substituted portion of a group consisting of the following: C 1-20 aliphatic, C 1-20 Acyl group, C 1-20 Heteroaliphatic, aryl, heteroaryl, hydroxyl protecting groups, phosphorus-linked functional groups, sulfur-linked functional groups, silicon-linked functional groups, C 2-20 Carbonates (e.g., partially -C(O)OR) c C 2-20 Carbamates (e.g., partially -C(O)N(R) c )2) C 2-20 Thioesters (e.g., partially -C(S)R) c C 2-20 Thiocarbonates (e.g., partially -C(S)OR) c C 2-20 Dithiocarbonates (e.g., partially -C(S)SR) c C 1-20 Thiocarbamates (e.g., partially -C(S)N(R) c 2) The sugar moiety, peptide, polymer chain, or linker to another ascaridin molecule via a bond or carbon-containing linker. Among them, R... c Each occurrence is independently selected from -H, optionally substituted C. 1-12 Aliphatic, optionally substituted C 1-12 Heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, polymer chain or linkage to another ascaridin molecule via a bond or carbon-containing linker, wherein R a and R b Together they can form optionally substituted rings, which optionally contain one or more heteroatoms and optionally one or more unsaturated sites.

8. The method of claim 7, wherein Z is selected from the group consisting of: (i)–CH(CH3)–R 1 , where R 1 C is arbitrarily substituted 1-40 Aliphatic groups; (ii)–CH(CH3)–(CH2) n –CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides; (iii)–CH(CH3)–(CH2) n –CH=CH-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides; (iv)–CH(CH3)–(CH2) n –CH(OH)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides; (v)–CH(CH3)–(CH2) n –C(O)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides; (vi)–(CH2) n –CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides; (vii)–(CH2) n –CH=CH-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides; (viii)–(CH2) n –CH(OH)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides; and (ix)–(CH2) n –C(O)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides.

9. The method of claim 7, wherein Z is selected from the group consisting of: (x)–CH(CH3)–(CH2) n –CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker. (xi)–CH(CH3)–(CH2) n –CH=CH-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker. (xii)–CH(CH3)–(CH2) n –CH(OH)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker. (xiii)–CH(CH3)–(CH2) n –C(O)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker. (xiv)–(CH2) n –CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker. (xv)–(CH2) n –CH=CH-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker. (xvi)–(CH2) n –CH(OH)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker. (xvii)–(CH2) n –C(O)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 Heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or linkages to another ascaridone molecule via bonds or carbon-containing linker portions; and (xix) optionally unsaturated optionally substituted C 2-40 Side chains terminate at chain ends containing functional groups of nitrogen, oxygen, or sulfur.

10. The method according to any one of claims 1 to 9, wherein one or more ascarosides comprise ascarosides selected from the group consisting of: ascr#9, ascr#10, ascr#16, ascr#18, ascr#20, ascr#22 and ascr#24.

11. The method according to any one of claims 1 to 9, wherein the one or more ascarosides include ascr#18.

12. The method according to any one of claims 1 to 11, wherein the one or more ascarosides and the one or more phytonutrients are applied simultaneously.

13. The method according to claim 12, wherein the one or more ascarosides and the one or more phytonutrients are contained in the same composition.

14. The method according to any one of claims 1 to 13, wherein the one or more ascaroside and the one or more phytonutrients are applied sequentially.

15. The method according to any one of claims 1 to 14, wherein the combination is used as a seed coating.

16. A composition comprising one or more ascaroside and one or more phytonutrients.

17. The composition according to claim 16, wherein the one or more ascarosides and the one or more phytonutrients are present in an effective amount.

18. The composition according to claim 16 or 17, wherein the one or more phytonutrients comprise one or more macronutrients selected from the group consisting of nitrogen-containing nutrients, phosphorus-containing nutrients, potassium-containing nutrients, calcium-containing nutrients, magnesium-containing nutrients, sulfur-containing nutrients, and combinations thereof.

19. The composition according to claim 16 or 17, wherein the one or more phytonutrients comprise one or more micronutrients selected from the group consisting of: boron-containing nutrients, chlorine-containing nutrients, copper-containing nutrients, iodine-iron-containing nutrients, manganese-containing nutrients, molybdenum-containing nutrients, zinc-containing nutrients, and combinations thereof.

20. The composition according to claim 16 or 17, wherein the one or more phytonutrients comprise one or more macronutrients and one or more micronutrients.

21. The composition according to any one of claims 16 to 20, wherein the one or more ascarosides comprises an ascaroside having structure (I): in: Z represents C, which is arbitrarily substituted. 3-40 Aliphatic groups, and R a and R b Each of them is independently -H or an optionally substituted portion of a group consisting of the following: C 1-20 aliphatic, C 1-20 Acyl group, C 1-20 Heteroaliphatic, aryl, heteroaryl, hydroxyl protecting groups, phosphorus-linked functional groups, sulfur-linked functional groups, silicon-linked functional groups, C 2-20 Carbonates (e.g., partially -C(O)OR) c C 2-20 Carbamates (e.g., partially -C(O)N(R) c )2) C 2-20 Thioesters (e.g., partially -C(S)R) c C 2-20 Thiocarbonates (e.g., partially -C(S)OR) c C 2-20 Dithiocarbonates (e.g., partially -C(S)SR) c C 1-20 Thiocarbamates (e.g., partially -C(S)N(R) c 2) The sugar moiety, peptide, polymer chain, or linker to another ascaridin molecule via a bond or carbon-containing linker. Among them, R... c Each occurrence is independently selected from -H, optionally substituted C. 1-12 Aliphatic, optionally substituted C 1-12 Heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, polymer chain or linkage to another ascaridin molecule via a bond or carbon-containing linker, wherein R a and R b Together they can form optionally substituted rings, which optionally contain one or more heteroatoms and optionally one or more unsaturated sites.

22. The composition of claim 21, wherein Z is selected from the group consisting of: (i)–CH(CH3)–R 1 , where R 1 C is arbitrarily substituted 1-40 Aliphatic groups; (ii)–CH(CH3)–(CH2) n –CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides; (iii)–CH(CH3)–(CH2) n –CH=CH-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides; (iv)–CH(CH3)–(CH2) n –CH(OH)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides; (v)–CH(CH3)–(CH2) n –C(O)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides; (vi)–(CH2) n –CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides; (vii)–(CH2) n –CH=CH-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides; (viii)–(CH2) n –CH(OH)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides; and (ix)–(CH2) n –C(O)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides.

23. The composition of claim 21, wherein Z is selected from the group consisting of: (x)–CH(CH3)–(CH2) n –CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker. (xi)–CH(CH3)–(CH2) n –CH=CH-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker. (xii)–CH(CH3)–(CH2) n –CH(OH)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker. (xiii)–CH(CH3)–(CH2) n –C(O)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker. (xiv)–(CH2) n –CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker. (xv)–(CH2) n –CH=CH-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker. (xvi)–(CH2) n –CH(OH)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker. (xvii)–(CH2) n –C(O)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 Heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or linkages to another ascaridone molecule via bonds or carbon-containing linker portions; and (xvii) Optionally unsaturated, Optionally substituted C 2-40 Side chains terminate at chain ends containing functional groups of nitrogen, oxygen, or sulfur.

24. The composition according to any one of claims 16 to 23, wherein the one or more ascarosides comprise ascarosides selected from the group consisting of: ascr#9, ascr#10, ascr#16, ascr#18, ascr#20, ascr#22 and ascr#24.

25. The composition according to any one of claims 16 to 23, wherein the one or more ascarosides comprises ascr#18.

26. The composition according to any one of claims 16 to 25, wherein the composition is in liquid form.

27. The composition of claim 26, wherein the liquid form is a sprayable formulation.

28. The composition according to any one of claims 16 to 25, wherein the composition is in solid form.

29. The composition of claim 28, wherein the solid form comprises powder or granules.

30. The composition according to any one of claims 16 to 29, wherein the composition is stable for a period of time greater than 6 months.

31. The composition according to any one of claims 16 to 30, wherein the composition further comprises one or more additional components selected from the group consisting of: surfactants including emulsifiers, dispersants, foaming agents, colorants, processing aids, lubricants, fillers, reinforcing agents, flame retardants, light stabilizers, ultraviolet radiation absorbers, climate stabilizers, plasticizers, release agents, fragrances, heat-insulating additives (e.g., silica), crosslinking agents, antioxidants, defoamers, buffers, pH adjusters, compatibilizers, drift control additives, expanders / adhesives, tackifiers, plant penetrants, safeners, spreading agents, and wetting agents.

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